#------------------------------------------------------------------------------
#$Date: 2023-03-04 19:32:12 +0100 (Sat 04 de Mar de 2023) $
#$Revision: 281516 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/22/7062208.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7062208
loop_
_publ_author_name
'Parakhin, Vladimir V.'
'Pokhvisneva, Galina V.'
'Ternikova, Tatyana V.'
'Shlykova, Nina I.'
'Samigullina, Aida I.'
'Nikitin, Sergei V.'
'Gordeev, Pavel B.'
'Smirnov, Gennady A.'
'Kon’kova, Tatyana S.'
'Lempert, David B.'
'Pivkina, Alla N.'
_publ_section_title
;
 Linking polynitro hexaazaisowurtzitane cages via an N,N'-methylene
 bridge: a promising strategy for designing energetic ensembles of CL-20
 derivatives and adjusting their properties
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2444
_journal_page_last               2455
_journal_paper_doi               10.1039/D2NJ05332B
_journal_volume                  47
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C13 H16 N20 O16'
_chemical_formula_sum            'C13 H16 N20 O16'
_chemical_formula_weight         708.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-06-16
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2022-09-22 deposited with the CCDC.	2022-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.3951(19)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.06669(19)
_cell_length_b                   13.5410(3)
_cell_length_c                   11.9398(2)
_cell_measurement_reflns_used    18074
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.4680
_cell_measurement_theta_min      3.2480
_cell_volume                     1278.49(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     58.00  92.00   0.50    0.81    --  107.75-165.00 123.00   68
  2  ω     97.00 138.00   0.50    0.81    --  107.75-165.00 123.00   82
  3  ω     69.00  95.00   0.50    0.81    --  107.75-125.00  30.00   52
  4  ω     38.00  66.00   0.50    0.81    --  107.75-125.00  30.00   56
  5  ω     46.00  81.00   0.50    0.20    --   48.45-116.00 -88.00   70
  6  ω     39.00  67.00   0.50    0.81    --  107.75-125.00-150.00   56
  7  ω     75.00 102.00   0.50    0.81    --  107.75-125.00-150.00   54
  8  ω     80.00 105.00   0.50    0.81    --  107.75-116.00 -88.00   50
  9  ω     76.00 105.00   0.50    0.81    --  107.75 -95.00 -90.00   58
 10  ω     43.00  69.00   0.50    0.81    --  107.75 -95.00 -90.00   52
 11  ω     73.00  99.00   0.50    0.81    --  107.75 -95.00 -60.00   52
 12  ω     88.00 114.00   0.50    0.81    --  107.75 -87.00-135.98   52
 13  ω     64.00 103.00   0.50    0.81    --  107.75 -95.00 -30.00   78
 14  ω     83.00 108.00   0.50    0.81    --  107.75-107.00  68.32   50
 15  ω     61.00  87.00   0.50    0.81    --  107.75 -88.00 151.88   52
 16  ω    103.00 128.00   0.50    0.81    --  107.75 -88.00 151.88   50
 17  ω     44.00  80.00   0.50    0.81    --  107.75 -87.00-135.98   72
 18  ω     78.00 103.00   0.50    0.81    --  107.75 -77.00 -90.00   50
 19  ω     37.00  69.00   0.50    0.81    --  107.75 -77.00-120.00   64
 20  ω     41.00  66.00   0.50    0.81    --  107.75 -72.00-119.61   50
 21  ω     37.00  69.00   0.50    0.81    --  107.75 -77.00 -90.00   64
 22  ω     39.00  64.00   0.50    0.81    --  107.75 -61.00 -60.00   50
 23  ω     39.00  71.00   0.50    0.81    --  107.75 -61.00 -90.00   64
 24  ω     40.00  65.00   0.50    0.81    --  107.75 -61.00 -30.00   50
 25  ω     40.00  70.00   0.50    0.81    --  107.75 -61.00   0.00   60
 26  ω     36.00  61.00   0.50    0.81    --  107.75 -61.00  60.00   50
 27  ω     45.00  71.00   0.50    0.81    --  107.75 -61.00  90.00   52
 28  ω    -24.00  25.00   0.50    0.20    --   48.45 -19.00-120.00   98
 29  ω    -23.00  42.00   0.50    0.20    --   48.45 -38.00   0.00  130
 30  ω    103.00 147.00   0.50    0.81    --  107.75  61.00 150.00   88
 31  ω    109.00 135.00   0.50    0.81    --  107.75  45.00  90.00   52
 32  ω    106.00 136.00   0.50    0.81    --  107.75  45.00  60.00   60
 33  ω    145.00 177.00   0.50    0.81    --  107.75  45.00  60.00   64
 34  ω    107.00 177.00   0.50    0.81    --  107.75  45.00   0.00  140
 35  ω     99.00 124.00   0.50    0.81    --  107.75  30.00 -60.00   50
 36  ω    143.00 171.00   0.50    0.81    --  107.75  30.00 -60.00   56
 37  ω    148.00 175.00   0.50    0.81    --  107.75  35.00 -90.64   54
 38  ω    130.00 165.00   0.50    0.81    --  107.75  45.00-120.00   70
 39  ω    101.00 126.00   0.50    0.81    --  107.75  45.00-120.00   50
 40  ω    115.00 140.00   0.50    0.81    --  107.75 116.00  -0.00   50
 41  ω     96.00 139.00   0.50    0.81    --  107.75 125.00  90.00   86
 42  ω     98.00 123.00   0.50    0.81    --  107.75 125.00 120.00   50
 43  ω     70.00 113.00   0.50    0.81    --  107.75 165.00 146.00   86
 44  ω    143.00 169.00   0.50    0.81    --  107.75 125.00 120.00   52
 45  ω    146.00 172.00   0.50    0.81    --  107.75 125.00  90.00   52
 46  ω    -24.00   2.00   0.50    0.20    --  -48.45  19.00-150.00   52
 47  ω    -83.00 -19.00   0.50    0.20    --  -48.45 116.00  -0.00  128
 48  ω    -50.00 -15.00   0.50    0.81    --  -86.25  45.00-150.00   70
 49  ω   -119.00 -75.00   0.50    0.20    --  -48.45-125.00 120.00   88
 50  ω   -120.00 -47.00   0.50    0.20    --  -48.45-165.00 123.00  146
 51  ω   -120.00 -74.00   0.50    0.20    --  -48.45-125.00 -30.00   92
 52  ω   -119.00 -91.00   0.50    0.81    --  -86.25-116.00 -88.00   56
 53  ω     81.00 107.00   0.50    0.81    --  107.75-116.00 -88.00   52
 54  ω    -68.00 -37.00   0.50    0.20    --  -48.70 -57.00  30.00   62
 55  ω   -108.00 -82.00   0.50    0.20    --  -48.70 -57.00  30.00   52
 56  ω   -111.00 -75.00   0.50    0.20    --  -48.70-125.00-150.00   72
 57  ω    -23.00  26.00   0.50    0.20    --  -48.70  19.00 -30.00   98
 58  ω    -17.00   9.00   0.50    0.20    --   48.70 -19.00 -90.00   52
 59  ω    -49.00 -14.00   0.50    0.81    --  -86.25  45.00-180.00   70
 60  ω    -63.00 -36.00   0.50    0.81    --  -86.25  61.00  60.00   54
 61  ω     42.00  68.00   0.50    0.81    --  107.75 -61.00 120.00   52
 62  ω     44.00  82.00   0.50    0.81    --  107.75 -77.00 120.00   76
 63  ω     36.00  61.00   0.50    0.81    --  107.75 -56.00 -60.77   50
 64  ω    110.00 136.00   0.50    0.81    --  107.75 125.00 -90.00   52
 65  ω     43.00  69.00   0.50    0.81    --  107.75 -77.00   0.00   52
 66  ω    111.00 137.00   0.50    0.81    --  107.75  45.00 150.00   52
 67  ω    142.00 178.00   0.50    0.81    --  107.75  45.00 150.00   72
 68  ω     81.00 107.00   0.50    0.81    --  107.75-105.00 -32.81   52
 69  ω     62.00 106.00   0.50    0.81    --  107.75-125.00-120.00   88
 70  ω     73.00 108.00   0.50    0.81    --  107.75-109.00-142.50   70
 71  ω     71.00  96.00   0.50    0.81    --  107.75 -95.00   0.00   50
 72  ω     74.00 106.00   0.50    0.81    --  107.75-101.00  75.63   64
 73  ω     53.00 103.00   0.50    0.81    --  107.75-125.00 -60.00  100
 74  ω    104.00 130.00   0.50    0.81    --  107.75  30.00-150.00   52
 75  ω    139.00 165.00   0.50    0.81    --  107.75 125.00 -90.00   52
 76  ω     38.00  64.00   0.50    0.81    --  107.75-105.00 -32.81   52
 77  ω     38.00  64.00   0.50    0.81    --  107.75 -95.00   0.00   52
 78  ω     36.00  61.00   0.50    0.81    --  107.75 -61.00-150.00   50
 79  ω     41.00  67.00   0.50    0.81    --  107.75 -77.00  30.00   52
 80  ω     71.00  97.00   0.50    0.81    --  107.75 -77.00  30.00   52
 81  ω     92.00 151.00   0.50    0.81    --  107.75  77.00-120.00  118
 82  ω    103.00 129.00   0.50    0.81    --  107.75  15.00-150.00   52
 83  ω    138.00 164.00   0.50    0.81    --  107.75  15.00-150.00   52
 84  ω     74.00  99.00   0.50    0.81    --  107.75 -95.00 150.00   50
 85  ω    101.00 136.00   0.50    0.81    --  107.75  31.00-141.81   70
 86  ω     65.00  91.00   0.50    0.81    --  107.75-103.00 -42.87   52
 87  ω    101.00 128.00   0.50    0.81    --  107.75  30.00 150.00   54
 88  ω    153.00 178.00   0.50    0.81    --  107.75  15.00  30.00   50
 89  ω     94.00 119.00   0.50    0.81    --  107.75  61.00   0.00   50
 90  ω     37.00  63.00   0.50    0.81    --  107.75 -95.00  90.00   52
 91  ω     69.00  94.00   0.50    0.81    --  107.75 -77.00 -30.00   50
 92  ω     80.00 105.00   0.50    0.81    --  107.75 -95.00-150.00   50
 93  ω     77.00 110.00   0.50    0.81    --  107.75-125.00  90.00   66
 94  ω     40.00 105.00   0.50    0.81    --  107.75-125.00 150.00  130
 95  ω    152.00 177.00   0.50    0.81    --  107.75  30.00-180.00   50
 96  ω    149.00 174.00   0.50    0.81    --  107.75  15.00 120.00   50
 97  ω    130.00 156.00   0.50    0.81    --  107.75  30.00-120.00   52
 98  ω    128.00 154.00   0.50    0.81    --  107.75  15.00  90.00   52
 99  ω     83.00 108.00   0.50    0.81    --  107.75 -79.00 138.36   50
100  ω     63.00 103.00   0.50    0.81    --  107.75-101.00 127.57   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0690478000
_diffrn_orient_matrix_UB_12      0.0795305000
_diffrn_orient_matrix_UB_13      0.0710003000
_diffrn_orient_matrix_UB_21      -0.1027378000
_diffrn_orient_matrix_UB_22      -0.0793777000
_diffrn_orient_matrix_UB_23      0.0487838000
_diffrn_orient_matrix_UB_31      0.1505244000
_diffrn_orient_matrix_UB_32      -0.0176092000
_diffrn_orient_matrix_UB_33      0.0995033000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24639
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.802
_diffrn_reflns_theta_min         3.777
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.487
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.576
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.57a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             724
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 2321 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     450
_refine_ls_number_reflns         5296
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0310
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0478P)²+0.3294P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0827
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.950
_reflns_number_gt                5119
_reflns_number_total             5296
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj05332b2.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 7062208--7062213.cif.'
_cod_database_code               7062208
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     PGV-2022
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.755
_reflns_odcompleteness_completeness 92.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     86.18
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C6(H6), C3(H3), C5(H5A), C1(H1), C2(H2), C10(H10), C9(H9), C8(H8),
 C7(H7), C12(H12), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.293
_oxdiff_exptl_absorpt_empirical_full_min 0.655
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8112(3) 0.42228(15) 0.62080(16) 0.0213(4) Uani 1 1 d . . . . .
O2 O 1.0043(2) 0.40544(16) 0.77485(17) 0.0225(4) Uani 1 1 d . . . . .
O5 O 0.6506(3) 0.71799(15) 0.73758(16) 0.0245(4) Uani 1 1 d . . . . .
O6 O 0.8834(3) 0.68549(16) 0.86012(18) 0.0250(4) Uani 1 1 d . . . . .
O3 O 0.8296(3) 0.35357(17) 1.10409(17) 0.0260(4) Uani 1 1 d . . . . .
O4 O 0.6003(3) 0.26658(17) 1.04331(19) 0.0276(5) Uani 1 1 d . . . . .
O7 O 0.7161(3) 0.62394(17) 1.16892(17) 0.0250(4) Uani 1 1 d . . . . .
O8 O 0.4531(3) 0.58304(16) 1.15433(17) 0.0235(4) Uani 1 1 d . . . . .
O13 O 0.4737(3) 0.70234(15) 0.37897(17) 0.0241(4) Uani 1 1 d . . . . .
O14 O 0.2375(3) 0.73325(15) 0.25959(17) 0.0238(4) Uani 1 1 d . . . . .
O16 O 0.2610(3) 0.39382(15) 0.11654(16) 0.0233(4) Uani 1 1 d . . . . .
O15 O 0.1030(2) 0.52451(16) 0.07869(16) 0.0212(4) Uani 1 1 d . . . . .
O11 O -0.3124(3) 0.42949(18) 0.3261(2) 0.0317(5) Uani 1 1 d . . . . .
O12 O -0.1923(3) 0.29456(16) 0.4047(2) 0.0308(5) Uani 1 1 d . . . . .
O10 O -0.1675(3) 0.64416(16) 0.5203(2) 0.0267(4) Uani 1 1 d . . . . .
O9 O 0.0243(3) 0.60619(16) 0.66980(17) 0.0244(4) Uani 1 1 d . . . . .
N1 N 0.7480(3) 0.46623(16) 0.78661(18) 0.0146(4) Uani 1 1 d . . . . .
N3 N 0.6406(3) 0.62065(16) 0.88342(18) 0.0152(4) Uani 1 1 d . . . . .
N2 N 0.6923(3) 0.36752(16) 0.92481(18) 0.0156(4) Uani 1 1 d . . . . .
N4 N 0.5937(3) 0.52450(17) 1.02448(18) 0.0146(4) Uani 1 1 d . . . . .
N5 N 0.3940(3) 0.41989(16) 0.89650(18) 0.0159(4) Uani 1 1 d . . . . .
N6 N 0.4592(3) 0.52291(16) 0.73198(18) 0.0141(4) Uani 1 1 d . . . . .
N7 N 0.8625(3) 0.42637(17) 0.72400(19) 0.0172(4) Uani 1 1 d . . . . .
N9 N 0.7320(3) 0.67754(16) 0.82244(19) 0.0181(5) Uani 1 1 d . . . . .
N8 N 0.7082(3) 0.32765(17) 1.0311(2) 0.0199(5) Uani 1 1 d . . . . .
N10 N 0.5870(3) 0.58285(17) 1.12091(18) 0.0172(4) Uani 1 1 d . . . . .
N13 N 0.2600(3) 0.59774(16) 0.36621(18) 0.0146(4) Uani 1 1 d . . . . .
N14 N 0.1608(3) 0.46513(17) 0.25651(18) 0.0161(4) Uani 1 1 d . . . . .
N11 N 0.0613(3) 0.56004(16) 0.49818(18) 0.0152(4) Uani 1 1 d . . . . .
N12 N -0.0363(3) 0.42568(17) 0.39173(19) 0.0175(4) Uani 1 1 d . . . . .
N15 N 0.2417(3) 0.35078(17) 0.41660(19) 0.0150(4) Uani 1 1 d . . . . .
N16 N 0.3507(3) 0.49941(16) 0.53722(18) 0.0136(4) Uani 1 1 d . . . . .
N19 N 0.3299(3) 0.68232(16) 0.33188(19) 0.0173(4) Uani 1 1 d . . . . .
N20 N 0.1781(3) 0.46187(17) 0.14448(19) 0.0169(4) Uani 1 1 d . . . . .
N18 N -0.1896(3) 0.38078(19) 0.3745(2) 0.0218(5) Uani 1 1 d . . . . .
N17 N -0.0355(3) 0.60478(16) 0.5682(2) 0.0193(5) Uani 1 1 d . . . . .
C4 C 0.5647(3) 0.43741(18) 0.7485(2) 0.0141(5) Uani 1 1 d . . . . .
H4 H 0.549227 0.397827 0.676446 0.017 Uiso 1 1 calc R U . . .
C6 C 0.4694(3) 0.58334(18) 0.8315(2) 0.0143(5) Uani 1 1 d . . . . .
H6 H 0.387348 0.639367 0.815400 0.017 Uiso 1 1 calc R U . . .
C3 C 0.5224(3) 0.37324(19) 0.8479(2) 0.0152(5) Uani 1 1 d . . . . .
H3 H 0.484540 0.305933 0.819226 0.018 Uiso 1 1 calc R U . . .
C5 C 0.4320(3) 0.51916(19) 0.9334(2) 0.0150(5) Uani 1 1 d . . . . .
H5A H 0.335349 0.548050 0.963348 0.018 Uiso 1 1 calc R U . . .
C1 C 0.7912(3) 0.45530(19) 0.9100(2) 0.0152(5) Uani 1 1 d . . . . .
H1 H 0.915098 0.443721 0.937024 0.018 Uiso 1 1 calc R U . . .
C2 C 0.7298(3) 0.55098(19) 0.9663(2) 0.0145(5) Uani 1 1 d . . . . .
H2 H 0.825352 0.583509 1.019584 0.017 Uiso 1 1 calc R U . . .
C13 C 0.4385(3) 0.57014(19) 0.6204(2) 0.0146(5) Uani 1 1 d . . . . .
H13A H 0.550104 0.587057 0.603025 0.017 Uiso 1 1 calc R U . . .
H13B H 0.371322 0.631492 0.618880 0.017 Uiso 1 1 calc R U . . .
C10 C 0.3684(3) 0.51564(18) 0.4216(2) 0.0132(5) Uani 1 1 d . . . . .
H10 H 0.489468 0.528297 0.418387 0.016 Uiso 1 1 calc R U . . .
C9 C 0.3006(3) 0.42306(19) 0.3469(2) 0.0138(5) Uani 1 1 d . . . . .
H9 H 0.391894 0.394736 0.310893 0.017 Uiso 1 1 calc R U . . .
C8 C 0.1049(3) 0.55748(19) 0.2994(2) 0.0152(5) Uani 1 1 d . . . . .
H8 H 0.052133 0.602789 0.236213 0.018 Uiso 1 1 calc R U . . .
C7 C -0.0208(3) 0.53197(19) 0.3829(2) 0.0165(5) Uani 1 1 d . . . . .
H7 H -0.133219 0.564754 0.358627 0.020 Uiso 1 1 calc R U . . .
C12 C 0.1790(3) 0.47863(18) 0.5467(2) 0.0142(5) Uani 1 1 d . . . . .
H12 H 0.172502 0.466847 0.628437 0.017 Uiso 1 1 calc R U . . .
C11 C 0.1131(3) 0.38573(19) 0.4727(2) 0.0151(5) Uani 1 1 d . . . . .
H11 H 0.077890 0.332680 0.521414 0.018 Uiso 1 1 calc R U . . .
H5 H 0.348(5) 0.383(3) 0.947(3) 0.024(9) Uiso 1 1 d . . . . .
H15 H 0.229(5) 0.291(3) 0.389(4) 0.031(10) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0637
0 -1 0 0.0693
0 0 1 0.0157
0 0 -1 0.0061
3 -4 4 0.0415
-1 -1 -1 0.0522
-1 0 1 0.1023
1 1 1 0.0659
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N7 N1 C4 116.6(2) . . ?
N7 N1 C1 116.7(2) . . ?
C1 N1 C4 107.7(2) . . ?
N9 N3 C6 121.5(2) . . ?
N9 N3 C2 118.8(2) . . ?
C2 N3 C6 111.0(2) . . ?
N8 N2 C3 120.0(2) . . ?
N8 N2 C1 118.8(2) . . ?
C1 N2 C3 109.87(19) . . ?
N10 N4 C5 116.4(2) . . ?
N10 N4 C2 114.0(2) . . ?
C2 N4 C5 106.86(19) . . ?
C3 N5 H5 117(2) . . ?
C5 N5 C3 114.3(2) . . ?
C5 N5 H5 113(2) . . ?
C4 N6 C6 114.48(19) . . ?
C4 N6 C13 116.1(2) . . ?
C6 N6 C13 119.0(2) . . ?
O1 N7 N1 115.2(2) . . ?
O2 N7 O1 126.2(2) . . ?
O2 N7 N1 118.4(2) . . ?
O5 N9 N3 115.8(2) . . ?
O6 N9 O5 126.9(2) . . ?
O6 N9 N3 117.3(2) . . ?
O3 N8 O4 126.4(2) . . ?
O3 N8 N2 117.6(2) . . ?
O4 N8 N2 116.0(2) . . ?
O7 N10 O8 125.0(2) . . ?
O7 N10 N4 118.3(2) . . ?
O8 N10 N4 116.6(2) . . ?
N19 N13 C10 121.1(2) . . ?
N19 N13 C8 120.6(2) . . ?
C8 N13 C10 109.3(2) . . ?
N20 N14 C9 118.6(2) . . ?
N20 N14 C8 117.9(2) . . ?
C8 N14 C9 108.17(19) . . ?
N17 N11 C7 118.5(2) . . ?
N17 N11 C12 118.5(2) . . ?
C7 N11 C12 108.0(2) . . ?
N18 N12 C7 121.5(2) . . ?
N18 N12 C11 122.1(2) . . ?
C7 N12 C11 109.7(2) . . ?
C9 N15 H15 116(3) . . ?
C11 N15 C9 113.9(2) . . ?
C11 N15 H15 117(3) . . ?
C10 N16 C13 115.4(2) . . ?
C10 N16 C12 112.7(2) . . ?
C12 N16 C13 114.8(2) . . ?
O13 N19 O14 126.0(2) . . ?
O13 N19 N13 117.3(2) . . ?
O14 N19 N13 116.6(2) . . ?
O16 N20 O15 124.9(2) . . ?
O16 N20 N14 117.2(2) . . ?
O15 N20 N14 117.9(2) . . ?
O11 N18 N12 117.0(2) . . ?
O12 N18 O11 126.1(2) . . ?
O12 N18 N12 116.9(2) . . ?
O10 N17 N11 116.6(2) . . ?
O9 N17 O10 126.6(2) . . ?
O9 N17 N11 116.6(2) . . ?
N1 C4 H4 110.3 . . ?
N1 C4 C3 105.21(19) . . ?
N6 C4 N1 110.7(2) . . ?
N6 C4 H4 110.3 . . ?
N6 C4 C3 110.0(2) . . ?
C3 C4 H4 110.3 . . ?
N3 C6 H6 110.3 . . ?
N3 C6 C5 99.74(19) . . ?
N6 C6 N3 115.9(2) . . ?
N6 C6 H6 110.3 . . ?
N6 C6 C5 109.7(2) . . ?
C5 C6 H6 110.3 . . ?
N2 C3 C4 100.63(19) . . ?
N2 C3 H3 110.2 . . ?
N5 C3 N2 115.1(2) . . ?
N5 C3 C4 110.3(2) . . ?
N5 C3 H3 110.2 . . ?
C4 C3 H3 110.2 . . ?
N4 C5 C6 104.96(19) . . ?
N4 C5 H5A 110.1 . . ?
N5 C5 N4 111.4(2) . . ?
N5 C5 C6 110.1(2) . . ?
N5 C5 H5A 110.1 . . ?
C6 C5 H5A 110.1 . . ?
N1 C1 N2 100.27(19) . . ?
N1 C1 H1 111.6 . . ?
N1 C1 C2 108.3(2) . . ?
N2 C1 H1 111.6 . . ?
N2 C1 C2 112.9(2) . . ?
C2 C1 H1 111.6 . . ?
N3 C2 N4 99.59(19) . . ?
N3 C2 C1 113.4(2) . . ?
N3 C2 H2 111.3 . . ?
N4 C2 C1 109.3(2) . . ?
N4 C2 H2 111.3 . . ?
C1 C2 H2 111.3 . . ?
N6 C13 N16 106.7(2) . . ?
N6 C13 H13A 110.4 . . ?
N6 C13 H13B 110.4 . . ?
N16 C13 H13A 110.4 . . ?
N16 C13 H13B 110.4 . . ?
H13A C13 H13B 108.6 . . ?
N13 C10 H10 110.3 . . ?
N13 C10 C9 103.63(18) . . ?
N16 C10 N13 112.5(2) . . ?
N16 C10 H10 110.3 . . ?
N16 C10 C9 109.5(2) . . ?
C9 C10 H10 110.3 . . ?
N14 C9 C10 103.4(2) . . ?
N14 C9 H9 110.3 . . ?
N15 C9 N14 112.8(2) . . ?
N15 C9 C10 109.57(19) . . ?
N15 C9 H9 110.3 . . ?
C10 C9 H9 110.3 . . ?
N13 C8 N14 102.9(2) . . ?
N13 C8 H8 112.1 . . ?
N13 C8 C7 108.9(2) . . ?
N14 C8 H8 112.1 . . ?
N14 C8 C7 108.3(2) . . ?
C7 C8 H8 112.1 . . ?
N11 C7 C8 107.9(2) . . ?
N11 C7 H7 112.0 . . ?
N12 C7 N11 102.7(2) . . ?
N12 C7 C8 109.6(2) . . ?
N12 C7 H7 112.0 . . ?
C8 C7 H7 112.0 . . ?
N11 C12 H12 110.2 . . ?
N11 C12 C11 104.75(19) . . ?
N16 C12 N11 111.9(2) . . ?
N16 C12 H12 110.2 . . ?
N16 C12 C11 109.7(2) . . ?
C11 C12 H12 110.2 . . ?
N12 C11 C12 102.4(2) . . ?
N12 C11 H11 110.6 . . ?
N15 C11 N12 112.7(2) . . ?
N15 C11 C12 109.6(2) . . ?
N15 C11 H11 110.6 . . ?
C12 C11 H11 110.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N7 1.221(3) . ?
O2 N7 1.217(3) . ?
O5 N9 1.223(3) . ?
O6 N9 1.220(3) . ?
O3 N8 1.226(3) . ?
O4 N8 1.230(3) . ?
O7 N10 1.219(3) . ?
O8 N10 1.223(3) . ?
O13 N19 1.215(3) . ?
O14 N19 1.234(3) . ?
O16 N20 1.223(3) . ?
O15 N20 1.231(3) . ?
O11 N18 1.234(3) . ?
O12 N18 1.223(3) . ?
O10 N17 1.227(3) . ?
O9 N17 1.214(3) . ?
N1 N7 1.406(3) . ?
N1 C4 1.510(3) . ?
N1 C1 1.453(3) . ?
N3 N9 1.371(3) . ?
N3 C6 1.486(3) . ?
N3 C2 1.451(3) . ?
N2 N8 1.362(3) . ?
N2 C3 1.493(3) . ?
N2 C1 1.462(3) . ?
N4 N10 1.406(3) . ?
N4 C5 1.526(3) . ?
N4 C2 1.455(3) . ?
N5 C3 1.431(3) . ?
N5 C5 1.429(3) . ?
N5 H5 0.92(4) . ?
N6 C4 1.427(3) . ?
N6 C6 1.431(3) . ?
N6 C13 1.457(3) . ?
N13 N19 1.374(3) . ?
N13 C10 1.486(3) . ?
N13 C8 1.451(3) . ?
N14 N20 1.373(3) . ?
N14 C9 1.510(3) . ?
N14 C8 1.456(3) . ?
N11 N17 1.391(3) . ?
N11 C7 1.455(3) . ?
N11 C12 1.495(3) . ?
N12 N18 1.357(3) . ?
N12 C7 1.450(3) . ?
N12 C11 1.490(3) . ?
N15 C9 1.425(3) . ?
N15 C11 1.423(3) . ?
N15 H15 0.87(5) . ?
N16 C13 1.458(3) . ?
N16 C10 1.432(3) . ?
N16 C12 1.440(3) . ?
C4 H4 1.0000 . ?
C4 C3 1.562(3) . ?
C6 H6 1.0000 . ?
C6 C5 1.572(3) . ?
C3 H3 1.0000 . ?
C5 H5A 1.0000 . ?
C1 H1 1.0000 . ?
C1 C2 1.584(3) . ?
C2 H2 1.0000 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C10 H10 1.0000 . ?
C10 C9 1.573(3) . ?
C9 H9 1.0000 . ?
C8 H8 1.0000 . ?
C8 C7 1.594(4) . ?
C7 H7 1.0000 . ?
C12 H12 1.0000 . ?
C12 C11 1.568(3) . ?
C11 H11 1.0000 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5 H5 O16 0.92(4) 2.27(4) 3.048(3) 142(3) 1_556 yes
N15 H15 O5 0.87(5) 2.19(4) 2.830(3) 130(4) 2_646 yes
N15 H15 O10 0.87(5) 2.36(4) 2.988(3) 129(4) 2_546 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C4 C3 N2 -4.5(2) . . . . ?
N1 C4 C3 N5 117.4(2) . . . . ?
N1 C1 C2 N3 3.1(3) . . . . ?
N1 C1 C2 N4 113.2(2) . . . . ?
N3 C6 C5 N4 -3.8(2) . . . . ?
N3 C6 C5 N5 -123.9(2) . . . . ?
N2 C1 C2 N3 -107.0(2) . . . . ?
N2 C1 C2 N4 3.1(3) . . . . ?
N6 C4 C3 N2 -123.8(2) . . . . ?
N6 C4 C3 N5 -1.8(3) . . . . ?
N6 C6 C5 N4 118.4(2) . . . . ?
N6 C6 C5 N5 -1.7(3) . . . . ?
N7 N1 C4 N6 -128.1(2) . . . . ?
N7 N1 C4 C3 113.1(2) . . . . ?
N7 N1 C1 N2 -96.8(2) . . . . ?
N7 N1 C1 C2 144.7(2) . . . . ?
N9 N3 C6 N6 58.7(3) . . . . ?
N9 N3 C6 C5 176.3(2) . . . . ?
N9 N3 C2 N4 168.7(2) . . . . ?
N9 N3 C2 C1 -75.4(3) . . . . ?
N8 N2 C3 N5 53.0(3) . . . . ?
N8 N2 C3 C4 171.5(2) . . . . ?
N8 N2 C1 N1 175.2(2) . . . . ?
N8 N2 C1 C2 -69.7(3) . . . . ?
N10 N4 C5 N5 -133.8(2) . . . . ?
N10 N4 C5 C6 107.0(2) . . . . ?
N10 N4 C2 N3 -92.0(2) . . . . ?
N10 N4 C2 C1 149.0(2) . . . . ?
N13 C10 C9 N14 0.4(2) . . . . ?
N13 C10 C9 N15 -120.2(2) . . . . ?
N13 C8 C7 N11 1.4(3) . . . . ?
N13 C8 C7 N12 -109.8(2) . . . . ?
N14 C8 C7 N11 112.5(2) . . . . ?
N14 C8 C7 N12 1.4(3) . . . . ?
N11 C12 C11 N12 -0.8(2) . . . . ?
N11 C12 C11 N15 119.1(2) . . . . ?
N16 C10 C9 N14 120.6(2) . . . . ?
N16 C10 C9 N15 0.1(3) . . . . ?
N16 C12 C11 N12 -120.9(2) . . . . ?
N16 C12 C11 N15 -1.1(3) . . . . ?
N19 N13 C10 N16 115.7(2) . . . . ?
N19 N13 C10 C9 -126.1(2) . . . . ?
N19 N13 C8 N14 112.7(2) . . . . ?
N19 N13 C8 C7 -132.6(2) . . . . ?
N20 N14 C9 N15 -125.6(2) . . . . ?
N20 N14 C9 C10 116.2(2) . . . . ?
N20 N14 C8 N13 -103.5(2) . . . . ?
N20 N14 C8 C7 141.4(2) . . . . ?
N18 N12 C7 N11 116.9(2) . . . . ?
N18 N12 C7 C8 -128.5(2) . . . . ?
N18 N12 C11 N15 112.7(3) . . . . ?
N18 N12 C11 C12 -129.6(2) . . . . ?
N17 N11 C7 N12 -104.6(2) . . . . ?
N17 N11 C7 C8 139.6(2) . . . . ?
N17 N11 C12 N16 -123.3(2) . . . . ?
N17 N11 C12 C11 118.0(2) . . . . ?
C4 N1 N7 O1 39.6(3) . . . . ?
C4 N1 N7 O2 -145.0(2) . . . . ?
C4 N1 C1 N2 36.5(2) . . . . ?
C4 N1 C1 C2 -82.0(2) . . . . ?
C4 N6 C6 N3 57.3(3) . . . . ?
C4 N6 C6 C5 -54.7(3) . . . . ?
C4 N6 C13 N16 64.6(3) . . . . ?
C6 N3 N9 O5 19.7(3) . . . . ?
C6 N3 N9 O6 -162.9(2) . . . . ?
C6 N3 C2 N4 -43.3(2) . . . . ?
C6 N3 C2 C1 72.7(3) . . . . ?
C6 N6 C4 N1 -59.1(3) . . . . ?
C6 N6 C4 C3 56.7(3) . . . . ?
C6 N6 C13 N16 -152.3(2) . . . . ?
C3 N2 N8 O3 -155.3(2) . . . . ?
C3 N2 N8 O4 26.6(3) . . . . ?
C3 N2 C1 N1 -41.2(2) . . . . ?
C3 N2 C1 C2 73.9(3) . . . . ?
C3 N5 C5 N4 -59.9(3) . . . . ?
C3 N5 C5 C6 56.2(3) . . . . ?
C5 N4 N10 O7 -149.0(2) . . . . ?
C5 N4 N10 O8 35.6(3) . . . . ?
C5 N4 C2 N3 38.1(2) . . . . ?
C5 N4 C2 C1 -81.0(2) . . . . ?
C5 N5 C3 N2 58.6(3) . . . . ?
C5 N5 C3 C4 -54.4(3) . . . . ?
C1 N1 N7 O1 168.7(2) . . . . ?
C1 N1 N7 O2 -15.8(3) . . . . ?
C1 N1 C4 N6 98.5(2) . . . . ?
C1 N1 C4 C3 -20.3(3) . . . . ?
C1 N2 N8 O3 -15.4(4) . . . . ?
C1 N2 N8 O4 166.5(2) . . . . ?
C1 N2 C3 N5 -90.2(3) . . . . ?
C1 N2 C3 C4 28.4(2) . . . . ?
C2 N3 N9 O5 164.3(2) . . . . ?
C2 N3 N9 O6 -18.3(3) . . . . ?
C2 N3 C6 N6 -88.4(2) . . . . ?
C2 N3 C6 C5 29.3(2) . . . . ?
C2 N4 N10 O7 -23.9(3) . . . . ?
C2 N4 N10 O8 160.7(2) . . . . ?
C2 N4 C5 N5 97.4(2) . . . . ?
C2 N4 C5 C6 -21.8(2) . . . . ?
C13 N6 C4 N1 85.6(3) . . . . ?
C13 N6 C4 C3 -158.6(2) . . . . ?
C13 N6 C6 N3 -86.3(3) . . . . ?
C13 N6 C6 C5 161.7(2) . . . . ?
C13 N16 C10 N13 -77.0(3) . . . . ?
C13 N16 C10 C9 168.3(2) . . . . ?
C13 N16 C12 N11 76.9(3) . . . . ?
C13 N16 C12 C11 -167.35(19) . . . . ?
C10 N13 N19 O13 -23.3(3) . . . . ?
C10 N13 N19 O14 159.9(2) . . . . ?
C10 N13 C8 N14 -34.8(3) . . . . ?
C10 N13 C8 C7 79.9(2) . . . . ?
C10 N16 C13 N6 -159.4(2) . . . . ?
C10 N16 C12 N11 -57.9(3) . . . . ?
C10 N16 C12 C11 57.8(3) . . . . ?
C9 N14 N20 O16 29.6(3) . . . . ?
C9 N14 N20 O15 -153.8(2) . . . . ?
C9 N14 C8 N13 34.7(2) . . . . ?
C9 N14 C8 C7 -80.5(2) . . . . ?
C9 N15 C11 N12 56.6(3) . . . . ?
C9 N15 C11 C12 -56.8(3) . . . . ?
C8 N13 N19 O13 -167.0(2) . . . . ?
C8 N13 N19 O14 16.2(3) . . . . ?
C8 N13 C10 N16 -97.0(2) . . . . ?
C8 N13 C10 C9 21.2(3) . . . . ?
C8 N14 N20 O16 163.3(2) . . . . ?
C8 N14 N20 O15 -20.0(3) . . . . ?
C8 N14 C9 N15 96.6(2) . . . . ?
C8 N14 C9 C10 -21.7(3) . . . . ?
C7 N11 N17 O10 -21.1(3) . . . . ?
C7 N11 N17 O9 163.3(2) . . . . ?
C7 N11 C12 N16 98.2(2) . . . . ?
C7 N11 C12 C11 -20.5(3) . . . . ?
C7 N12 N18 O11 16.2(4) . . . . ?
C7 N12 N18 O12 -166.4(2) . . . . ?
C7 N12 C11 N15 -95.5(3) . . . . ?
C7 N12 C11 C12 22.1(3) . . . . ?
C12 N11 N17 O10 -155.3(2) . . . . ?
C12 N11 N17 O9 29.1(3) . . . . ?
C12 N11 C7 N12 33.8(3) . . . . ?
C12 N11 C7 C8 -82.0(2) . . . . ?
C12 N16 C13 N6 67.0(3) . . . . ?
C12 N16 C10 N13 57.6(3) . . . . ?
C12 N16 C10 C9 -57.1(3) . . . . ?
C11 N12 N18 O11 164.7(2) . . . . ?
C11 N12 N18 O12 -17.9(4) . . . . ?
C11 N12 C7 N11 -35.0(3) . . . . ?
C11 N12 C7 C8 79.5(2) . . . . ?
C11 N15 C9 N14 -57.2(3) . . . . ?
C11 N15 C9 C10 57.4(3) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0008 0.9998 -0.0026 0.0793 -0.0796 -0.0178
-0.0008 -0.9998 0.0026 -0.0793 0.0796 0.0178
0.0006 -0.0000 0.9980 0.0708 0.0486 0.0994
-0.0006 0.0000 -0.9980 -0.0708 -0.0486 -0.0994
3.4402 -3.6288 3.7916 -0.2569 0.1196 0.9590
-1.0007 -1.0003 -1.0003 -0.0815 0.1334 -0.2326
-0.9987 -0.0006 0.9930 0.1394 0.1511 -0.0515
1.0007 1.0003 1.0003 0.0815 -0.1334 0.2326
