#------------------------------------------------------------------------------
#$Date: 2023-10-06 02:46:59 +0200 (Fri 06 de Oct de 2023) $
#$Revision: 286795 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/95/7159541.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_7159541
loop_
_publ_author_name
'Komogortsev, Andrey N.'
'Lichitskii, Boris V.'
'Melekhina, Valeriya G.'
_publ_section_title
;
 1,1'-Carbonyldiimidazole-mediated transformation of allomaltol containing
 hydrazides into substituted 3-acetyltetronic acids.
;
_journal_issue                   35
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7224
_journal_page_last               7230
_journal_paper_doi               10.1039/d3ob01136d
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C13 H15 N O5, 2(C3 H4 N2)'
_chemical_formula_sum            'C19 H23 N5 O5'
_chemical_formula_weight         401.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-03-20
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-06-15 deposited with the CCDC.	2023-08-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.9400(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.5566(2)
_cell_length_b                   9.65170(10)
_cell_length_c                   21.0321(2)
_cell_measurement_reflns_used    20854
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.6830
_cell_measurement_theta_min      4.2270
_cell_volume                     3948.59(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -75.00  24.00   0.50    0.40    --  -48.70  87.00  59.00  198
  2  ω    -21.00  75.00   0.50    0.40    --   48.70 -87.00 -58.00  192
  3  ω   -112.00 -14.00   0.50    1.60    --  -86.25  87.00  59.00  196
  4  ω     36.00 134.00   0.50    1.60    --  107.75 -87.00 -58.00  196
  5  ω    101.00 178.00   0.50    1.60    --  107.75  87.00  59.00  154
  6  ω   -118.00 -73.00   0.50    0.40    --  -48.70-125.00   0.00   90
  7  ω   -118.00 -73.00   0.50    0.40    --  -48.70-125.00  30.00   90
  8  ω    -26.00  26.00   0.50    0.40    --  -48.70  19.00-180.00  104
  9  ω    -25.00  26.00   0.50    0.40    --   48.70 -19.00-150.00  102
 10  ω   -158.00 -79.00   0.50    1.60    --  -86.25 -87.00 -58.00  158
 11  ω    -51.00 -14.00   0.50    1.60    --  -86.25  45.00-120.00   74
 12  ω    101.00 176.00   0.50    1.60    --  107.75 116.00 -74.79  150
 13  ω     45.00  71.00   0.50    1.60    --  107.75 -61.00 -60.00   52
 14  ω    102.00 150.00   0.50    1.60    --  107.75  30.00 -30.00   96
 15  ω    142.00 173.00   0.50    1.60    --  107.75 125.00-120.00   62
 16  ω     63.00 105.00   0.50    1.60    --  107.75-105.00  13.72   84
 17  ω     41.00  67.00   0.50    1.60    --  107.75 -61.00 120.00   52
 18  ω     46.00  72.00   0.50    1.60    --  107.75 -77.00 -30.00   52
 19  ω     95.00 136.00   0.50    1.60    --  107.75 125.00-120.00   82
 20  ω     37.00  70.00   0.50    1.60    --  107.75 -61.00-150.00   66
 21  ω     50.00  76.00   0.50    1.60    --  107.75-125.00-150.00   52
 22  ω    131.00 177.00   0.50    1.60    --  107.75 125.00-180.00   92
 23  ω     40.00 117.00   0.50    1.60    --  107.75-135.00 151.77  154
 24  ω     60.00 105.00   0.50    1.60    --  107.75 -95.00 -90.00   90
 25  ω    114.00 140.00   0.50    1.60    --  107.75  45.00   0.00   52
 26  ω    143.00 168.00   0.50    1.60    --  107.75  45.00   0.00   50
 27  ω     84.00 111.00   0.50    1.60    --  107.75-125.00-180.00   54
 28  ω     37.00  65.00   0.50    1.60    --  107.75 -57.00-107.27   56
 29  ω     98.00 135.00   0.50    1.60    --  107.75  30.00  30.00   74
 30  ω     44.00  84.00   0.50    1.60    --  107.75 -95.00  90.00   80
 31  ω     95.00 121.00   0.50    1.60    --  107.75 125.00-180.00   52
 32  ω     76.00 101.00   0.50    1.60    --  107.75 -77.00-120.00   50
 33  ω     42.00 106.00   0.50    1.60    --  107.75-105.00  55.78  128
 34  ω     98.00 126.00   0.50    1.60    --  107.75  30.00 150.00   56
 35  ω    131.00 176.00   0.50    1.60    --  107.75  30.00 150.00   90
 36  ω     48.00  81.00   0.50    1.60    --  107.75 -77.00   0.00   66
 37  ω     57.00  83.00   0.50    1.60    --  107.75 -95.00  30.00   52
 38  ω     36.00  63.00   0.50    1.60    --  107.75 -61.00-120.00   54
 39  ω     74.00 104.00   0.50    1.60    --  107.75 -77.00-180.00   60
 40  ω     38.00  71.00   0.50    1.60    --  107.75 -95.00   0.00   66
 41  ω     43.00  77.00   0.50    1.60    --  107.75-125.00-180.00   68
 42  ω    111.00 136.00   0.50    1.60    --  107.75  73.00  49.59   50
 43  ω    134.00 160.00   0.50    1.60    --  107.75  30.00-180.00   52
;
_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      -0.0143988000
_diffrn_orient_matrix_UB_12      -0.1429129000
_diffrn_orient_matrix_UB_13      -0.0310499000
_diffrn_orient_matrix_UB_21      -0.0719710000
_diffrn_orient_matrix_UB_22      -0.0007380000
_diffrn_orient_matrix_UB_23      0.0238004000
_diffrn_orient_matrix_UB_31      -0.0299406000
_diffrn_orient_matrix_UB_32      0.0705734000
_diffrn_orient_matrix_UB_33      -0.0624379000
_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  0.0258
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            26476
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.853
_diffrn_reflns_theta_min         4.227
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.832
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.53a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.285
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         4156
_refine_ls_number_restraints     32
_refine_ls_restrained_S_all      1.283
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0562
_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)+(0.0108P)²+10.2680P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1260
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4091
_reflns_number_total             4156
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01136d2.cif
_cod_data_source_block           kjnoim
_cod_depositor_comments
'Adding full bibliography for 7159539--7159545.cif.'
_cod_database_code               7159541
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C187  H170  N17  O17  '
_chemical_oxdiff_usercomment     KJMOIM
_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   0.936
_shelx_estimated_absorpt_t_min   0.892
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O5-N1 \\sim O5A-N1A
 with sigma of 0.02
 N3-C15 \\sim N3A-C15A
 with sigma of 0.02
 N5-C17 \\sim N5A-C17A
 with sigma of 0.02
 N3A-N3 \\sim C16-C16A
 with sigma of 0.03
 N5-C19 \\sim N5A-C19A
 with sigma of 0.02
 N3-C16 \\sim N3A-C16A
 with sigma of 0.02
 N5-C18 \\sim N5A-C18A
 with sigma of 0.04
 N3-N2 \\sim N3A-N2A
 with sigma of 0.04
 N3-C14 \\sim N3A-C14A
 with sigma of 0.04
 N4A-N5 \\sim N5A-N4
 with sigma of 0.03
 N3A-C15A \\sim C15-N3
 with sigma of 0.03
 N4-C19 \\sim C19A-N5A
 with sigma of 0.03
 N5-N4 \\sim N5A-N4A
 with sigma of 0.03
 O5-C11 \\sim O5A-C11
 with sigma of 0.04
 C18A-N4A \\sim C17-N5
 with sigma of 0.03
 N5-C19 \\sim C19A-N4A
 with sigma of 0.03
 C17A-N5A \\sim C18-N4
 with sigma of 0.03
 N1-O5 \\sim N1A-O5A
 with sigma of 0.03
 N1-C11 \\sim N1A-C11
 with sigma of 0.02
 C11-N1 \\sim N1-N1A
 with sigma of 0.03
 C15A-C14A \\sim C14-C15
 with sigma of 0.03
 N2-C16 \\sim N2A-C16A
 with sigma of 0.02
 N2-C14 \\sim N2A-C14A
 with sigma of 0.02
 C16A-N2 \\sim N2A-C16
 with sigma of 0.03
 C15-C16 \\sim C15A-C16A
 with sigma of 0.04
 C16-C14 \\sim C16A-C14A
 with sigma of 0.04
 C14-C14A \\sim N2A-N2
 with sigma of 0.03
 N2-N2A \\sim C16A-C16
 with sigma of 0.03
 C15-C14 \\sim C15A-C14A
 with sigma of 0.02
 N2-C15 \\sim N2A-C15A
 with sigma of 0.04
 N4-C19 \\sim N4A-C19A
 with sigma of 0.02
 C17-C19 \\sim C17A-C19A
 with sigma of 0.04
 N4-C18 \\sim N4A-C18A
 with sigma of 0.02
 N4-C17 \\sim N4A-C17A
 with sigma of 0.04
 C18A-C17A \\sim C17-C18
 with sigma of 0.03
 C17-C18 \\sim C17A-C18A
 with sigma of 0.02
 C19-C18 \\sim C19A-C18A
 with sigma of 0.04
 C18-C19 \\sim C19A-C17A
 with sigma of 0.03
3. Uiso/Uaniso restraints and constraints
Uanis(N3A) = Uanis(N3)
Uanis(N4) = Uanis(N5)
Uanis(N5) = Uanis(N4A)
Uanis(N4A) = Uanis(N5A)
Uanis(O5A) = Uanis(O5)
Uanis(N5A) = Uanis(N4)
Uanis(N1) = Uanis(N1A)
Uanis(C16A) = Uanis(C16)
Uanis(N2A) = Uanis(N2)
Uanis(C15) = Uanis(C15A)
Uanis(C14) = Uanis(C14A)
Uanis(C17) = Uanis(C18A)
Uanis(C19) = Uanis(C19A)
Uanis(C17A) = Uanis(C18)
4. Others
 Sof(O5A)=Sof(H5A)=Sof(N1A)=1-FVAR(1)
 Sof(O5)=Sof(H5)=Sof(N1)=FVAR(1)
 Sof(N2A)=Sof(N3A)=Sof(H3E)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=
 Sof(H16A)=1-FVAR(2)
 Sof(N2)=Sof(N3)=Sof(H3)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=
 FVAR(2)
 Sof(N4A)=Sof(N5A)=Sof(H5K)=Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=
 Sof(H19A)=1-FVAR(3)
 Sof(N4)=Sof(N5)=Sof(H5D)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=Sof(C19)=
 Sof(H19)=FVAR(3)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5B,H5C), C12(H12A,H12B)
5.b Aromatic/amide H refined with riding coordinates:
 C8(H8), N3(H3), C14(H14), C15(H15), C16(H16), N3A(H3E), C14A(H14A),
 C15A(H15A), C16A(H16A), C17(H17), C18(H18), C19(H19), C17A(H17A), C18A(H18A),
 C19A(H19A)
5.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
5.d Idealised tetrahedral OH refined as rotating group:
 O5(H5), O5A(H5A)
;
_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 1.365
_oxdiff_exptl_absorpt_empirical_full_min 0.797
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
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 0.56872(8) 0.46681(16) 0.42995(7) 0.0269(3) Uani 1 1 d . . . . .
O2 O 0.80230(7) 0.50956(14) 0.41040(6) 0.0201(3) Uani 1 1 d . . . . .
O3 O 0.91951(8) 0.19079(16) 0.35566(8) 0.0307(4) Uani 1 1 d . . . . .
O4 O 0.77898(8) 0.17150(15) 0.33506(7) 0.0268(3) Uani 1 1 d . . . . .
O5 O 0.71498(11) -0.0337(2) 0.27907(11) 0.0266(5) Uani 0.714(3) 1 d D . P A 1
H5 H 0.690714 -0.098898 0.262685 0.040 Uiso 0.714(3) 1 calc R U P A 1
O5A O 0.6337(3) 0.0509(6) 0.2636(3) 0.0266(5) Uani 0.286(3) 1 d D . P A 2
H5A H 0.621682 -0.029927 0.252614 0.040 Uiso 0.286(3) 1 calc R U P A 2
N1 N 0.67429(15) 0.0863(3) 0.28147(13) 0.0238(6) Uani 0.714(3) 1 d D . P A 1
N1A N 0.7016(4) 0.0495(8) 0.2911(4) 0.0238(6) Uani 0.286(3) 1 d D . P A 2
C1 C 0.69490(10) 0.3940(2) 0.37564(9) 0.0207(4) Uani 1 1 d . . . . .
C2 C 0.66495(11) 0.5412(2) 0.37366(11) 0.0262(5) Uani 1 1 d . . . . .
H2A H 0.685953 0.594433 0.410927 0.031 Uiso 1 1 calc R U . . .
H2B H 0.676353 0.588714 0.334389 0.031 Uiso 1 1 calc R U . . .
C3 C 0.58731(12) 0.5379(3) 0.37467(11) 0.0305(5) Uani 1 1 d . . . . .
H3A H 0.569458 0.633900 0.374536 0.037 Uiso 1 1 calc R U . . .
H3B H 0.566048 0.490820 0.335721 0.037 Uiso 1 1 calc R U . . .
C4 C 0.59050(11) 0.3257(2) 0.43046(10) 0.0241(4) Uani 1 1 d . . . . .
H4A H 0.568811 0.278305 0.391747 0.029 Uiso 1 1 calc R U . . .
H4B H 0.575288 0.278296 0.468309 0.029 Uiso 1 1 calc R U . . .
C5 C 0.66808(11) 0.3153(2) 0.43226(9) 0.0209(4) Uani 1 1 d . . . . .
H5B H 0.681525 0.216633 0.430547 0.025 Uiso 1 1 calc R U . . .
H5C H 0.689594 0.354539 0.473013 0.025 Uiso 1 1 calc R U . . .
C6 C 0.77185(10) 0.3943(2) 0.38301(9) 0.0190(4) Uani 1 1 d . . . . .
C7 C 0.87248(10) 0.5178(2) 0.41881(9) 0.0210(4) Uani 1 1 d . . . . .
C8 C 0.91202(11) 0.4133(2) 0.40183(10) 0.0244(4) Uani 1 1 d . . . . .
H8 H 0.960540 0.421989 0.409770 0.029 Uiso 1 1 calc R U . . .
C9 C 0.88397(11) 0.2890(2) 0.37216(10) 0.0232(4) Uani 1 1 d . . . . .
C10 C 0.80967(11) 0.2885(2) 0.36335(9) 0.0205(4) Uani 1 1 d . . . . .
C11 C 0.71076(12) 0.1817(2) 0.30978(10) 0.0278(5) Uani 1 1 d D . . . .
C12 C 0.67582(12) 0.3182(3) 0.31175(10) 0.0275(5) Uani 1 1 d . . . . .
H12A H 0.625426 0.304117 0.305470 0.033 Uiso 1 1 calc R U . . .
H12B H 0.688830 0.376628 0.276241 0.033 Uiso 1 1 calc R U . . .
C13 C 0.89628(12) 0.6534(2) 0.44639(11) 0.0264(5) Uani 1 1 d . . . . .
H13A H 0.871233 0.674941 0.483178 0.040 Uiso 1 1 calc R U . . .
H13B H 0.887642 0.725932 0.413963 0.040 Uiso 1 1 calc R U . . .
H13C H 0.945638 0.648594 0.460202 0.040 Uiso 1 1 calc R U . . .
N2 N 0.3711(4) 0.2748(7) 0.2733(3) 0.0284(11) Uani 0.580(10) 1 d D . P B 1
N3 N 0.4127(8) 0.0753(13) 0.3102(9) 0.026(2) Uani 0.580(10) 1 d D . P B 1
H3 H 0.414671 -0.006123 0.329162 0.031 Uiso 0.580(10) 1 calc R U P B 1
C14 C 0.4412(5) 0.2724(8) 0.2696(4) 0.0304(15) Uani 0.580(10) 1 d D . P B 1
H14 H 0.467573 0.346849 0.255476 0.036 Uiso 0.580(10) 1 calc R U P B 1
C15 C 0.4667(6) 0.1466(13) 0.2895(10) 0.0301(16) Uani 0.580(10) 1 d D . P B 1
H15 H 0.512589 0.114757 0.289015 0.036 Uiso 0.580(10) 1 calc R U P B 1
C16 C 0.3561(6) 0.1530(13) 0.2962(9) 0.0290(14) Uani 0.580(10) 1 d D . P B 1
H16 H 0.310791 0.123625 0.302090 0.035 Uiso 0.580(10) 1 calc R U P B 1
N2A N 0.3958(6) 0.2855(10) 0.2662(5) 0.0284(11) Uani 0.420(10) 1 d D . P B 2
N3A N 0.4199(11) 0.0730(19) 0.3001(13) 0.026(2) Uani 0.420(10) 1 d D . P B 2
H3E H 0.413197 -0.013063 0.311830 0.031 Uiso 0.420(10) 1 calc R U P B 2
C14A C 0.4647(6) 0.2560(12) 0.2628(6) 0.0304(15) Uani 0.420(10) 1 d D . P B 2
H14A H 0.495982 0.316300 0.244839 0.036 Uiso 0.420(10) 1 calc R U P B 2
C15A C 0.4818(9) 0.129(2) 0.2884(15) 0.0301(16) Uani 0.420(10) 1 d D . P B 2
H15A H 0.526249 0.089316 0.296286 0.036 Uiso 0.420(10) 1 calc R U P B 2
C16A C 0.3711(8) 0.1720(19) 0.2907(12) 0.0290(14) Uani 0.420(10) 1 d D . P B 2
H16A H 0.324976 0.161587 0.300451 0.035 Uiso 0.420(10) 1 calc R U P B 2
N4 N 0.4269(7) 0.0164(9) 0.5106(5) 0.0258(8) Uani 0.50(2) 1 d D . P C 1
N5 N 0.3163(9) 0.0456(18) 0.5186(11) 0.0258(8) Uani 0.50(2) 1 d D . P C 1
H5D H 0.276(2) 0.039(4) 0.508(2) 0.016(12) Uiso 0.50(2) 1 d . . P C 1
C17 C 0.3522(17) 0.091(6) 0.5744(17) 0.029(2) Uani 0.50(2) 1 d D . P C 1
H17 H 0.332736 0.128945 0.610010 0.035 Uiso 0.50(2) 1 calc R U P C 1
C18 C 0.4201(17) 0.071(5) 0.5700(11) 0.0333(14) Uani 0.50(2) 1 d D . P C 1
H18 H 0.456456 0.092159 0.602060 0.040 Uiso 0.50(2) 1 calc R U P C 1
C19 C 0.3641(8) 0.005(3) 0.4808(7) 0.0230(19) Uani 0.50(2) 1 d D . P C 1
H19 H 0.354038 -0.028057 0.438324 0.028 Uiso 0.50(2) 1 calc R U P C 1
N4A N 0.3258(10) 0.0387(18) 0.5187(12) 0.0258(8) Uani 0.50(2) 1 d D . P C 2
N5A N 0.4394(7) 0.0350(9) 0.5246(5) 0.0258(8) Uani 0.50(2) 1 d D . P C 2
H5K H 0.486(4) 0.024(8) 0.513(4) 0.06(2) Uiso 0.50(2) 1 d . . P C 2
C17A C 0.4208(17) 0.083(5) 0.5820(11) 0.0333(14) Uani 0.50(2) 1 d D . P C 2
H17A H 0.451299 0.111987 0.617680 0.040 Uiso 0.50(2) 1 calc R U P C 2
C18A C 0.3513(17) 0.083(6) 0.5786(17) 0.029(2) Uani 0.50(2) 1 d D . P C 2
H18A H 0.324602 0.109261 0.611946 0.035 Uiso 0.50(2) 1 calc R U P C 2
C19A C 0.3809(7) 0.008(3) 0.4888(8) 0.0230(19) Uani 0.50(2) 1 d D . P C 2
H19A H 0.378604 -0.029599 0.446818 0.028 Uiso 0.50(2) 1 calc R U P C 2
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
-1 -1 -1 0.0172
1 1 1 0.0709
0 1 -1 0.0727
0 -1 1 0.0148
0 -1 -1 0.0152
0 1 1 0.0684
1 0 0 0.0572
-1 0 1 0.0541
0 0 -1 0.0264
-1 1 0 0.0369
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
C4 O1 C3 111.32(17) . . ?
C6 O2 C7 119.42(16) . . ?
C10 O4 C11 117.61(17) . . ?
N1 O5 H5 109.5 . . ?
N1A O5A H5A 109.5 . . ?
C11 N1 O5 108.7(3) . . ?
C11 N1A O5A 101.9(6) . . ?
C2 C1 C5 108.40(17) . . ?
C2 C1 C12 110.99(17) . . ?
C6 C1 C2 112.15(17) . . ?
C6 C1 C5 109.78(16) . . ?
C6 C1 C12 103.98(16) . . ?
C12 C1 C5 111.54(17) . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 C1 111.01(18) . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
O1 C3 C2 111.09(17) . . ?
O1 C3 H3A 109.4 . . ?
O1 C3 H3B 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
O1 C4 H4A 109.4 . . ?
O1 C4 H4B 109.4 . . ?
O1 C4 C5 111.08(17) . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C1 C5 H5B 109.3 . . ?
C1 C5 H5C 109.3 . . ?
C4 C5 C1 111.47(17) . . ?
C4 C5 H5B 109.3 . . ?
C4 C5 H5C 109.3 . . ?
H5B C5 H5C 108.0 . . ?
O2 C6 C1 115.91(17) . . ?
C10 C6 O2 121.20(18) . . ?
C10 C6 C1 122.88(18) . . ?
O2 C7 C13 111.76(18) . . ?
C8 C7 O2 121.37(19) . . ?
C8 C7 C13 126.8(2) . . ?
C7 C8 H8 118.7 . . ?
C7 C8 C9 122.6(2) . . ?
C9 C8 H8 118.7 . . ?
O3 C9 C8 123.9(2) . . ?
O3 C9 C10 122.9(2) . . ?
C8 C9 C10 113.13(18) . . ?
O4 C10 C9 116.33(18) . . ?
C6 C10 O4 121.45(19) . . ?
C6 C10 C9 122.20(19) . . ?
O4 C11 C12 118.63(18) . . ?
N1 C11 O4 126.7(2) . . ?
N1 C11 C12 114.6(2) . . ?
N1A C11 O4 98.0(4) . . ?
N1A C11 C12 143.4(4) . . ?
C1 C12 H12A 109.2 . . ?
C1 C12 H12B 109.2 . . ?
C11 C12 C1 111.97(18) . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C16 N2 C14 105.5(6) . . ?
C15 N3 H3 126.4 . . ?
C16 N3 H3 126.4 . . ?
C16 N3 C15 107.1(7) . . ?
N2 C14 H14 125.3 . . ?
C15 C14 N2 109.4(6) . . ?
C15 C14 H14 125.3 . . ?
N3 C15 H15 127.0 . . ?
C14 C15 N3 106.1(7) . . ?
C14 C15 H15 127.0 . . ?
N2 C16 N3 111.6(7) . . ?
N2 C16 H16 124.2 . . ?
N3 C16 H16 124.2 . . ?
C16A N2A C14A 104.3(9) . . ?
C15A N3A H3E 125.8 . . ?
C16A N3A H3E 125.8 . . ?
C16A N3A C15A 108.5(11) . . ?
N2A C14A H14A 124.3 . . ?
C15A C14A N2A 111.3(9) . . ?
C15A C14A H14A 124.3 . . ?
N3A C15A H15A 128.0 . . ?
C14A C15A N3A 104.0(10) . . ?
C14A C15A H15A 128.0 . . ?
N2A C16A N3A 111.1(10) . . ?
N2A C16A H16A 124.4 . . ?
N3A C16A H16A 124.4 . . ?
C19 N4 C18 106.8(12) . . ?
C17 N5 H5D 131(4) . . ?
C19 N5 H5D 123(4) . . ?
C19 N5 C17 105.7(16) . . ?
N5 C17 H17 125.8 . . ?
C18 C17 N5 108(2) . . ?
C18 C17 H17 125.8 . . ?
N4 C18 H18 126.2 . . ?
C17 C18 N4 107.6(19) . . ?
C17 C18 H18 126.2 . . ?
N4 C19 N5 111.3(7) . . ?
N4 C19 H19 124.3 . . ?
N5 C19 H19 124.3 . . ?
C19A N4A C18A 105.6(16) . . ?
C17A N5A H5K 127(5) . . ?
C19A N5A H5K 127(5) . . ?
C19A N5A C17A 105.9(12) . . ?
N5A C17A H17A 126.0 . . ?
C18A C17A N5A 107.9(19) . . ?
C18A C17A H17A 126.0 . . ?
N4A C18A H18A 125.8 . . ?
C17A C18A N4A 108(2) . . ?
C17A C18A H18A 125.8 . . ?
N4A C19A H19A 123.9 . . ?
N5A C19A N4A 112.1(7) . . ?
N5A C19A H19A 123.9 . . ?
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 C3 1.429(3) . ?
O1 C4 1.427(3) . ?
O2 C6 1.361(2) . ?
O2 C7 1.368(2) . ?
O3 C9 1.246(3) . ?
O4 C10 1.384(2) . ?
O4 C11 1.388(3) . ?
O5 H5 0.8400 . ?
O5 N1 1.410(3) . ?
O5A H5A 0.8400 . ?
O5A N1A 1.392(8) . ?
N1 C11 1.274(3) . ?
N1A C11 1.342(8) . ?
C1 C2 1.536(3) . ?
C1 C5 1.549(3) . ?
C1 C6 1.497(3) . ?
C1 C12 1.541(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.521(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.517(3) . ?
C5 H5B 0.9900 . ?
C5 H5C 0.9900 . ?
C6 C10 1.351(3) . ?
C7 C8 1.341(3) . ?
C7 C13 1.487(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.435(3) . ?
C9 C10 1.446(3) . ?
C11 C12 1.486(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N2 C14 1.381(6) . ?
N2 C16 1.315(8) . ?
N3 H3 0.8800 . ?
N3 C15 1.369(8) . ?
N3 C16 1.345(9) . ?
C14 H14 0.9500 . ?
C14 C15 1.361(7) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
N2A C14A 1.386(8) . ?
N2A C16A 1.324(11) . ?
N3A H3E 0.8800 . ?
N3A C15A 1.372(11) . ?
N3A C16A 1.352(12) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.364(11) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
N4 C18 1.376(11) . ?
N4 C19 1.324(10) . ?
N5 H5D 0.80(5) . ?
N5 C17 1.375(13) . ?
N5 C19 1.347(10) . ?
C17 H17 0.9500 . ?
C17 C18 1.352(10) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N4A C18A 1.375(12) . ?
N4A C19A 1.337(11) . ?
N5A H5K 0.98(7) . ?
N5A C17A 1.378(13) . ?
N5A C19A 1.329(10) . ?
C17A H17A 0.9500 . ?
C17A C18A 1.353(10) . ?
C18A H18A 0.9500 . ?
C19A H19A 0.9500 . ?
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 H5D N5 0.80(5) 1.83(5) 2.63(4) 174(5) 2_556 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
O1 C4 C5 C1 -56.4(2) . . . . ?
O2 C6 C10 O4 -179.54(17) . . . . ?
O2 C6 C10 C9 2.2(3) . . . . ?
O2 C7 C8 C9 2.0(3) . . . . ?
O3 C9 C10 O4 -0.1(3) . . . . ?
O3 C9 C10 C6 178.2(2) . . . . ?
O4 C11 C12 C1 -40.8(3) . . . . ?
O5 N1 C11 O4 -0.6(4) . . . . ?
O5 N1 C11 C12 175.85(19) . . . . ?
O5A N1A C11 O4 -178.9(5) . . . . ?
O5A N1A C11 C12 1.0(10) . . . . ?
N1 C11 C12 C1 142.4(2) . . . . ?
N1A C11 C12 C1 139.3(6) . . . . ?
C1 C2 C3 O1 57.6(2) . . . . ?
C1 C6 C10 O4 -0.3(3) . . . . ?
C1 C6 C10 C9 -178.53(18) . . . . ?
C2 C1 C5 C4 51.1(2) . . . . ?
C2 C1 C6 O2 24.1(2) . . . . ?
C2 C1 C6 C10 -155.18(19) . . . . ?
C2 C1 C12 C11 173.44(18) . . . . ?
C3 O1 C4 C5 61.3(2) . . . . ?
C4 O1 C3 C2 -62.0(2) . . . . ?
C5 C1 C2 C3 -51.4(2) . . . . ?
C5 C1 C6 O2 -96.5(2) . . . . ?
C5 C1 C6 C10 84.3(2) . . . . ?
C5 C1 C12 C11 -65.6(2) . . . . ?
C6 O2 C7 C8 -1.4(3) . . . . ?
C6 O2 C7 C13 177.22(17) . . . . ?
C6 C1 C2 C3 -172.79(17) . . . . ?
C6 C1 C5 C4 173.91(17) . . . . ?
C6 C1 C12 C11 52.7(2) . . . . ?
C7 O2 C6 C1 179.98(16) . . . . ?
C7 O2 C6 C10 -0.7(3) . . . . ?
C7 C8 C9 O3 179.7(2) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C8 C9 C10 O4 -179.87(17) . . . . ?
C8 C9 C10 C6 -1.5(3) . . . . ?
C10 O4 C11 N1 179.2(2) . . . . ?
C10 O4 C11 N1A -177.2(4) . . . . ?
C10 O4 C11 C12 2.8(3) . . . . ?
C11 O4 C10 C6 19.2(3) . . . . ?
C11 O4 C10 C9 -162.41(18) . . . . ?
C12 C1 C2 C3 71.4(2) . . . . ?
C12 C1 C5 C4 -71.4(2) . . . . ?
C12 C1 C6 O2 144.10(17) . . . . ?
C12 C1 C6 C10 -35.2(3) . . . . ?
C13 C7 C8 C9 -176.4(2) . . . . ?
N2 C14 C15 N3 -5(2) . . . . ?
C14 N2 C16 N3 2.9(18) . . . . ?
C15 N3 C16 N2 -6(2) . . . . ?
C16 N2 C14 C15 1.2(15) . . . . ?
C16 N3 C15 C14 6(2) . . . . ?
N2A C14A C15A N3A 8(3) . . . . ?
C14A N2A C16A N3A -2(3) . . . . ?
C15A N3A C16A N2A 7(4) . . . . ?
C16A N2A C14A C15A -3(2) . . . . ?
C16A N3A C15A C14A -9(3) . . . . ?
N5 C17 C18 N4 1(6) . . . . ?
C17 N5 C19 N4 3(4) . . . . ?
C18 N4 C19 N5 -2(3) . . . . ?
C19 N4 C18 C17 0(5) . . . . ?
C19 N5 C17 C18 -2(5) . . . . ?
N5A C17A C18A N4A -2(6) . . . . ?
C17A N5A C19A N4A 2(3) . . . . ?
C18A N4A C19A N5A -3(4) . . . . ?
C19A N4A C18A C17A 3(5) . . . . ?
C19A N5A C17A C18A 0(5) . . . . ?
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
-1.0015 -1.0001 -0.9982 0.1883 0.0491 0.0217
1.0015 1.0001 0.9982 -0.1883 -0.0491 -0.0217
0.0008 0.9999 -0.9996 -0.1119 -0.0246 0.1330
-0.0008 -0.9999 0.9996 0.1119 0.0246 -0.1330
-0.0014 -1.0002 -0.9988 0.1740 -0.0229 -0.0082
0.0014 1.0002 0.9988 -0.1740 0.0229 0.0082
1.0002 -0.0001 -0.0006 -0.0144 -0.0720 -0.0299
-0.9999 0.0003 0.9998 -0.0167 0.0958 -0.0325
-0.0003 -0.0002 -0.9992 0.0311 -0.0238 0.0624
-0.9991 1.0001 0.0002 -0.1285 0.0712 0.1005
