#------------------------------------------------------------------------------
#$Date: 2019-11-17 06:23:00 +0100 (dom 17 de nov de 2019) $
#$Revision: 228645 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/93/1549300.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_1549300
loop_
_publ_author_name
'Rottschäfer, Dennis'
'Neumann, Beate'
'Stammler, Hans-Georg'
'Andrada, Diego M.'
'Ghadwal, Rajendra S.'
_publ_section_title
;
 Kekulé diradicaloids derived from a classical N-heterocyclic carbene.
;
_journal_issue                   22
_journal_name_full               'Chemical science'
_journal_page_first              4970
_journal_page_last               4976
_journal_paper_doi               10.1039/c8sc01209a
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C60 H80 N4, 2(I), 2(C H4 O)'
_chemical_formula_sum            'C62 H88 I2 N4 O2'
_chemical_formula_weight         1175.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-12-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-02-28 deposited with the CCDC.
2018-04-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.6225(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.01776(12)
_cell_length_b                   11.68842(10)
_cell_length_c                   18.61137(19)
_cell_measurement_reflns_used    68766
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      31.8190
_cell_measurement_theta_min      2.0570
_cell_volume                     3022.44(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.15e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.15e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.15e (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0951
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -93.00   5.00   1.00    1.25    --  -23.50 -77.00   0.00   98
  2  ω      6.00  93.00   1.00    1.25    --   24.78  57.00  60.00   87
  3  ω      6.00  93.00   1.00    1.25    --   24.78  57.00-120.00   87
  4  ω    -20.00  65.00   1.00    1.25    --   24.78 -99.00-150.00   85
  5  ω      6.00  93.00   1.00    1.25    --   24.78  57.00 150.00   87
  6  ω    -44.00  43.00   1.00    1.25    --   24.78 -57.00  90.00   87
  7  ω      6.00  83.00   1.00    1.25    --   24.78-130.00  58.60   77
  8  ω     -4.00  94.00   1.00    1.25    --   24.78  77.00 -60.00   98
  9  ω    -44.00  43.00   1.00    1.25    --   24.78 -57.00   0.00   87
 10  ω    -44.00  43.00   1.00    1.25    --   24.78 -57.00 -90.00   87
 11  ω    -95.00  48.00   1.00    1.25    --  -23.50   0.00-180.00  143
 12  ω    -95.00  48.00   1.00    1.25    --  -23.50   0.00-150.00  143
 13  ω     -4.00  94.00   1.00    1.25    --   24.78  77.00-180.00   98
 14  ω      3.00  95.00   1.00    1.25    --   24.78  38.00 120.00   92
 15  ω      6.00  93.00   1.00    1.25    --   24.78  57.00 130.00   87
 16  ω      6.00  93.00   1.00    1.25    --   24.78  57.00   0.00   87
 17  ω    -20.00  65.00   1.00    1.25    --   24.78 -99.00  90.00   85
 18  ω    -10.00  72.00   1.00    1.25    --   24.78-111.00-111.39   82
 19  ω    -46.00  47.00   1.00    1.25    --   24.78 -38.00 150.00   93
 20  ω    -95.00  48.00   1.00    1.25    --  -23.50   0.00 -90.00  143
 21  ω    -95.00  48.00   1.00    1.25    --  -23.50   0.00 -60.00  143
 22  ω    -95.00  48.00   1.00    1.25    --  -23.50   0.00 -30.00  143
 23  ω    -95.00  48.00   1.00    1.25    --  -23.50   0.00-120.00  143
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0418293000
_diffrn_orient_matrix_UB_12      -0.0209447000
_diffrn_orient_matrix_UB_13      0.0132613000
_diffrn_orient_matrix_UB_21      -0.0003972000
_diffrn_orient_matrix_UB_22      0.0488355000
_diffrn_orient_matrix_UB_23      0.0225820000
_diffrn_orient_matrix_UB_31      -0.0292732000
_diffrn_orient_matrix_UB_32      0.0292949000
_diffrn_orient_matrix_UB_33      -0.0281546000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            171581
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.028
_diffrn_reflns_theta_min         1.714
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.083
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.307
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.15e (Rigaku Oxford Diffraction, 2015)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1220
_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.308
_exptl_crystal_size_min          0.204
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         8848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0220
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0176P)²+1.7845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0482
_refine_ls_wR_factor_ref         0.0499
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8020
_reflns_number_total             8848
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8sc01209a2.cif
_cod_data_source_block           rottschaefer61
_cod_depositor_comments
'Adding full bibliography for 1549300--1549303.cif.'
_cod_database_code               1549300
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C62 H88 I1 N4 O2'
_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.
;
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C22(H22), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20), C29(H29), C30(H30)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C), C31(H31A,H31B,H31C)
;
_olex2_date_sample_data_collection 2017-12-06
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.223
_oxdiff_exptl_absorpt_empirical_full_min 0.849
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
N1 N 0.26909(7) 0.51231(8) 0.58241(5) 0.01220(18) Uani 1 1 d .
N2 N 0.38393(7) 0.45233(8) 0.66720(5) 0.01143(17) Uani 1 1 d .
C1 C 0.35998(8) 0.48017(9) 0.59792(6) 0.01064(19) Uani 1 1 d .
C2 C 0.22171(9) 0.51530(11) 0.64911(7) 0.0174(2) Uani 1 1 d .
H2A H 0.166590 0.464423 0.645082 0.021 Uiso 1 1 calc R
H2B H 0.201017 0.592183 0.659135 0.021 Uiso 1 1 calc R
C3 C 0.30177(9) 0.47408(11) 0.70809(7) 0.0172(2) Uani 1 1 d .
H3A H 0.317681 0.532399 0.744804 0.021 Uiso 1 1 calc R
H3B H 0.282830 0.404757 0.731118 0.021 Uiso 1 1 calc R
C4 C 0.22155(8) 0.54037(10) 0.51059(6) 0.0137(2) Uani 1 1 d .
C5 C 0.16590(8) 0.45485(11) 0.47184(7) 0.0169(2) Uani 1 1 d .
C6 C 0.12590(10) 0.48081(13) 0.40101(7) 0.0231(3) Uani 1 1 d .
H6 H 0.088855 0.426139 0.373783 0.028 Uiso 1 1 calc R
C7 C 0.14034(10) 0.58646(14) 0.37049(8) 0.0270(3) Uani 1 1 d .
H7 H 0.114650 0.601328 0.322738 0.032 Uiso 1 1 calc R
C8 C 0.19292(10) 0.66990(13) 0.41095(8) 0.0245(3) Uani 1 1 d .
H8 H 0.201116 0.740962 0.390137 0.029 Uiso 1 1 calc R
C9 C 0.23396(9) 0.64970(11) 0.48235(7) 0.0174(2) Uani 1 1 d .
C10 C 0.14598(9) 0.33915(11) 0.50428(8) 0.0198(2) Uani 1 1 d .
H10 H 0.187622 0.332010 0.550701 0.024 Uiso 1 1 calc R
C11 C 0.16841(11) 0.23936(13) 0.45622(9) 0.0309(3) Uani 1 1 d .
H11A H 0.124798 0.240759 0.411868 0.046 Uiso 1 1 calc GR
H11B H 0.161210 0.168541 0.481073 0.046 Uiso 1 1 calc GR
H11C H 0.233317 0.246064 0.445532 0.046 Uiso 1 1 calc GR
C12 C 0.04110(11) 0.33210(14) 0.51944(10) 0.0340(4) Uani 1 1 d .
H12A H 0.028840 0.392262 0.552119 0.051 Uiso 1 1 calc GR
H12B H 0.030181 0.259375 0.540893 0.051 Uiso 1 1 calc GR
H12C H -0.001287 0.340255 0.474796 0.051 Uiso 1 1 calc GR
C13 C 0.28670(9) 0.74485(11) 0.52639(8) 0.0206(3) Uani 1 1 d .
H13 H 0.316973 0.711938 0.572244 0.025 Uiso 1 1 calc R
C14 C 0.36628(11) 0.79695(14) 0.48773(9) 0.0318(3) Uani 1 1 d .
H14A H 0.407595 0.737212 0.474475 0.048 Uiso 1 1 calc GR
H14B H 0.403235 0.849922 0.519580 0.048 Uiso 1 1 calc GR
H14C H 0.337906 0.836363 0.444906 0.048 Uiso 1 1 calc GR
C15 C 0.21575(11) 0.83706(13) 0.54414(10) 0.0322(3) Uani 1 1 d .
H15A H 0.185467 0.871147 0.499992 0.048 Uiso 1 1 calc GR
H15B H 0.249718 0.894802 0.574040 0.048 Uiso 1 1 calc GR
H15C H 0.167602 0.803007 0.569523 0.048 Uiso 1 1 calc GR
C16 C 0.46189(8) 0.37518(10) 0.69317(6) 0.0126(2) Uani 1 1 d .
C17 C 0.45297(9) 0.25905(10) 0.67317(6) 0.0145(2) Uani 1 1 d .
C18 C 0.52720(10) 0.18535(11) 0.70086(7) 0.0198(2) Uani 1 1 d .
H18 H 0.522470 0.107810 0.689759 0.024 Uiso 1 1 calc R
C19 C 0.60782(10) 0.22583(12) 0.74463(7) 0.0221(3) Uani 1 1 d .
H19 H 0.657363 0.175824 0.761530 0.026 Uiso 1 1 calc R
C20 C 0.61488(9) 0.34060(12) 0.76330(7) 0.0205(2) Uani 1 1 d .
H20 H 0.669642 0.366862 0.792295 0.025 Uiso 1 1 calc R
C21 C 0.54126(9) 0.41754(10) 0.73936(6) 0.0153(2) Uani 1 1 d .
C22 C 0.36558(9) 0.21058(10) 0.62580(7) 0.0166(2) Uani 1 1 d .
H22 H 0.331131 0.274435 0.599931 0.020 Uiso 1 1 calc R
C23 C 0.29695(10) 0.15281(13) 0.67238(8) 0.0261(3) Uani 1 1 d .
H23A H 0.328404 0.088166 0.696993 0.039 Uiso 1 1 calc GR
H23B H 0.240196 0.127667 0.641883 0.039 Uiso 1 1 calc GR
H23C H 0.279315 0.206445 0.707391 0.039 Uiso 1 1 calc GR
C24 C 0.39224(10) 0.12525(13) 0.56927(8) 0.0249(3) Uani 1 1 d .
H24A H 0.436845 0.160326 0.541073 0.037 Uiso 1 1 calc GR
H24B H 0.335233 0.103105 0.537956 0.037 Uiso 1 1 calc GR
H24C H 0.421341 0.058820 0.593349 0.037 Uiso 1 1 calc GR
C25 C 0.54718(9) 0.54064(11) 0.76470(7) 0.0183(2) Uani 1 1 d .
H25 H 0.496980 0.583844 0.734551 0.022 Uiso 1 1 calc R
C26 C 0.52700(12) 0.54888(13) 0.84365(8) 0.0290(3) Uani 1 1 d .
H26A H 0.465413 0.515447 0.847804 0.044 Uiso 1 1 calc GR
H26B H 0.526829 0.627777 0.857964 0.044 Uiso 1 1 calc GR
H26C H 0.576126 0.508565 0.874526 0.044 Uiso 1 1 calc GR
C27 C 0.64424(10) 0.59598(12) 0.75665(8) 0.0257(3) Uani 1 1 d .
H27A H 0.693391 0.563335 0.791463 0.039 Uiso 1 1 calc GR
H27B H 0.640567 0.676865 0.764826 0.039 Uiso 1 1 calc GR
H27C H 0.659608 0.582442 0.708621 0.039 Uiso 1 1 calc GR
C28 C 0.43162(8) 0.48550(9) 0.54644(6) 0.0109(2) Uani 1 1 d .
C29 C 0.51128(8) 0.55601(10) 0.56650(6) 0.0135(2) Uani 1 1 d .
H29 H 0.518127 0.593329 0.611016 0.016 Uiso 1 1 calc R
C30 C 0.58029(8) 0.57048(10) 0.52007(6) 0.0136(2) Uani 1 1 d .
H30 H 0.633616 0.616903 0.533290 0.016 Uiso 1 1 calc R
I1 I 0.41279(2) 0.82305(2) 0.72122(2) 0.02068(3) Uani 1 1 d .
O1 O 0.61400(10) 0.80540(10) 0.62463(8) 0.0405(3) Uani 1 1 d .
C31 C 0.63576(10) 0.92208(12) 0.62316(8) 0.0250(3) Uani 1 1 d .
H31A H 0.584478 0.961767 0.594086 0.037 Uiso 1 1 calc GR
H31B H 0.694561 0.932578 0.602763 0.037 Uiso 1 1 calc GR
H31C H 0.643176 0.951977 0.671623 0.037 Uiso 1 1 calc GR
H1 H 0.5686(16) 0.8001(18) 0.6441(12) 0.047(6) 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 0.0033 0.0016 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
-3 0 5 0.1022
3 0 -5 0.1022
2 5 -2 0.1403
-2 -5 2 0.1403
4 0 5 0.1425
-4 0 -5 0.1425
5 -1 -5 0.1202
-1 3 5 0.1689
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
C1 N1 C2 110.43(9) . .
C1 N1 C4 125.24(9) . .
C4 N1 C2 124.33(9) . .
C1 N2 C3 110.02(9) . .
C1 N2 C16 123.92(9) . .
C16 N2 C3 122.52(9) . .
N1 C1 N2 113.15(10) . .
N1 C1 C28 124.33(10) . .
N2 C1 C28 122.23(10) . .
N1 C2 H2A 111.2 . .
N1 C2 H2B 111.2 . .
N1 C2 C3 102.96(9) . .
H2A C2 H2B 109.1 . .
C3 C2 H2A 111.2 . .
C3 C2 H2B 111.2 . .
N2 C3 C2 103.29(9) . .
N2 C3 H3A 111.1 . .
N2 C3 H3B 111.1 . .
C2 C3 H3A 111.1 . .
C2 C3 H3B 111.1 . .
H3A C3 H3B 109.1 . .
C5 C4 N1 117.89(10) . .
C9 C4 N1 119.16(11) . .
C9 C4 C5 122.94(11) . .
C4 C5 C10 123.12(11) . .
C6 C5 C4 117.12(12) . .
C6 C5 C10 119.74(12) . .
C5 C6 H6 119.4 . .
C7 C6 C5 121.25(13) . .
C7 C6 H6 119.4 . .
C6 C7 H7 119.9 . .
C8 C7 C6 120.10(13) . .
C8 C7 H7 119.9 . .
C7 C8 H8 119.3 . .
C7 C8 C9 121.42(13) . .
C9 C8 H8 119.3 . .
C4 C9 C13 122.86(11) . .
C8 C9 C4 117.07(12) . .
C8 C9 C13 120.05(12) . .
C5 C10 H10 107.8 . .
C5 C10 C11 112.54(12) . .
C5 C10 C12 110.56(11) . .
C11 C10 H10 107.8 . .
C11 C10 C12 110.06(12) . .
C12 C10 H10 107.8 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11B 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C10 C12 H12A 109.5 . .
C10 C12 H12B 109.5 . .
C10 C12 H12C 109.5 . .
H12A C12 H12B 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C9 C13 H13 107.9 . .
C9 C13 C14 111.80(12) . .
C9 C13 C15 110.43(11) . .
C14 C13 H13 107.9 . .
C14 C13 C15 110.84(12) . .
C15 C13 H13 107.9 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14B 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C17 C16 N2 118.36(10) . .
C21 C16 N2 119.10(10) . .
C21 C16 C17 122.49(11) . .
C16 C17 C22 123.27(11) . .
C18 C17 C16 117.49(11) . .
C18 C17 C22 119.20(11) . .
C17 C18 H18 119.5 . .
C19 C18 C17 121.08(12) . .
C19 C18 H18 119.5 . .
C18 C19 H19 119.9 . .
C18 C19 C20 120.22(12) . .
C20 C19 H19 119.9 . .
C19 C20 H20 119.4 . .
C19 C20 C21 121.21(12) . .
C21 C20 H20 119.4 . .
C16 C21 C25 122.20(11) . .
C20 C21 C16 117.43(11) . .
C20 C21 C25 120.35(11) . .
C17 C22 H22 107.9 . .
C17 C22 C23 110.71(11) . .
C17 C22 C24 112.94(10) . .
C23 C22 H22 107.9 . .
C24 C22 H22 107.9 . .
C24 C22 C23 109.26(11) . .
C22 C23 H23A 109.5 . .
C22 C23 H23B 109.5 . .
C22 C23 H23C 109.5 . .
H23A C23 H23B 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C22 C24 H24A 109.5 . .
C22 C24 H24B 109.5 . .
C22 C24 H24C 109.5 . .
H24A C24 H24B 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
C21 C25 H25 107.8 . .
C21 C25 C26 110.39(11) . .
C21 C25 C27 112.58(11) . .
C26 C25 H25 107.8 . .
C27 C25 H25 107.8 . .
C27 C25 C26 110.23(11) . .
C25 C26 H26A 109.5 . .
C25 C26 H26B 109.5 . .
C25 C26 H26C 109.5 . .
H26A C26 H26B 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C25 C27 H27A 109.5 . .
C25 C27 H27B 109.5 . .
C25 C27 H27C 109.5 . .
H27A C27 H27B 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C29 C28 C1 116.03(10) . .
C30 C28 C1 123.05(10) 3_666 .
C30 C28 C29 120.83(10) 3_666 .
C28 C29 H29 119.9 . .
C30 C29 C28 120.18(10) . .
C30 C29 H29 119.9 . .
C28 C30 H30 120.5 3_666 .
C29 C30 C28 119.00(10) . 3_666
C29 C30 H30 120.5 . .
C31 O1 H1 106.3(16) . .
O1 C31 H31A 109.5 . .
O1 C31 H31B 109.5 . .
O1 C31 H31C 109.5 . .
H31A C31 H31B 109.5 . .
H31A C31 H31C 109.5 . .
H31B C31 H31C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.3230(14) .
N1 C2 1.4839(14) .
N1 C4 1.4498(15) .
N2 C1 1.3291(14) .
N2 C3 1.4840(14) .
N2 C16 1.4494(14) .
C1 C28 1.4784(15) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C2 C3 1.5394(17) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C5 1.4066(17) .
C4 C9 1.4015(17) .
C5 C6 1.3958(18) .
C5 C10 1.5218(18) .
C6 H6 0.9300 .
C6 C7 1.385(2) .
C7 H7 0.9300 .
C7 C8 1.383(2) .
C8 H8 0.9300 .
C8 C9 1.3965(18) .
C9 C13 1.5146(19) .
C10 H10 0.9800 .
C10 C11 1.5278(19) .
C10 C12 1.5355(19) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 H13 0.9800 .
C13 C14 1.5317(19) .
C13 C15 1.532(2) .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C16 C17 1.4086(16) .
C16 C21 1.4030(17) .
C17 C18 1.3956(17) .
C17 C22 1.5207(17) .
C18 H18 0.9300 .
C18 C19 1.3859(19) .
C19 H19 0.9300 .
C19 C20 1.3860(19) .
C20 H20 0.9300 .
C20 C21 1.3964(17) .
C21 C25 1.5130(17) .
C22 H22 0.9800 .
C22 C23 1.5343(18) .
C22 C24 1.5316(18) .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
C24 H24A 0.9600 .
C24 H24B 0.9600 .
C24 H24C 0.9600 .
C25 H25 0.9800 .
C25 C26 1.5357(19) .
C25 C27 1.5318(19) .
C26 H26A 0.9600 .
C26 H26B 0.9600 .
C26 H26C 0.9600 .
C27 H27A 0.9600 .
C27 H27B 0.9600 .
C27 H27C 0.9600 .
C28 C29 1.3982(16) .
C28 C30 1.3905(16) 3_666
C29 H29 0.9300 .
C29 C30 1.3903(15) .
C30 H30 0.9300 .
O1 C31 1.3986(18) .
O1 H1 0.78(2) .
C31 H31A 0.9600 .
C31 H31B 0.9600 .
C31 H31C 0.9600 .
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_4
N1 C1 C28 C29 118.61(13) . .
N1 C1 C28 C30 -58.01(16) . 3_666
N1 C2 C3 N2 -0.35(12) . .
N1 C4 C5 C6 -175.86(10) . .
N1 C4 C5 C10 5.84(16) . .
N1 C4 C9 C8 175.19(11) . .
N1 C4 C9 C13 -6.50(17) . .
N2 C1 C28 C29 -54.74(15) . .
N2 C1 C28 C30 128.63(12) . 3_666
N2 C16 C17 C18 -177.72(10) . .
N2 C16 C17 C22 -0.09(16) . .
N2 C16 C21 C20 179.94(11) . .
N2 C16 C21 C25 1.64(17) . .
C1 N1 C2 C3 -1.95(13) . .
C1 N1 C4 C5 97.38(14) . .
C1 N1 C4 C9 -81.58(15) . .
C1 N2 C3 C2 2.55(13) . .
C1 N2 C16 C17 -66.82(15) . .
C1 N2 C16 C21 115.71(13) . .
C1 C28 C29 C30 -177.12(11) . .
C2 N1 C1 N2 3.87(14) . .
C2 N1 C1 C28 -170.02(10) . .
C2 N1 C4 C5 -82.33(14) . .
C2 N1 C4 C9 98.70(14) . .
C3 N2 C1 N1 -4.11(14) . .
C3 N2 C1 C28 169.93(10) . .
C3 N2 C16 C17 89.80(13) . .
C3 N2 C16 C21 -87.67(14) . .
C4 N1 C1 N2 -175.88(10) . .
C4 N1 C1 C28 10.23(18) . .
C4 N1 C2 C3 177.80(11) . .
C4 C5 C6 C7 -0.19(19) . .
C4 C5 C10 C11 -129.31(13) . .
C4 C5 C10 C12 107.16(14) . .
C4 C9 C13 C14 127.21(13) . .
C4 C9 C13 C15 -108.88(14) . .
C5 C4 C9 C8 -3.72(18) . .
C5 C4 C9 C13 174.59(11) . .
C5 C6 C7 C8 -1.9(2) . .
C6 C5 C10 C11 52.43(16) . .
C6 C5 C10 C12 -71.10(16) . .
C6 C7 C8 C9 1.2(2) . .
C7 C8 C9 C4 1.5(2) . .
C7 C8 C9 C13 -176.83(13) . .
C8 C9 C13 C14 -54.53(16) . .
C8 C9 C13 C15 69.38(16) . .
C9 C4 C5 C6 3.07(17) . .
C9 C4 C5 C10 -175.24(11) . .
C10 C5 C6 C7 178.18(12) . .
C16 N2 C1 N1 155.03(10) . .
C16 N2 C1 C28 -30.93(16) . .
C16 N2 C3 C2 -156.93(10) . .
C16 C17 C18 C19 -1.85(18) . .
C16 C17 C22 C23 -98.91(13) . .
C16 C17 C22 C24 138.20(12) . .
C16 C21 C25 C26 103.94(14) . .
C16 C21 C25 C27 -132.41(12) . .
C17 C16 C21 C20 2.57(17) . .
C17 C16 C21 C25 -175.73(11) . .
C17 C18 C19 C20 1.7(2) . .
C18 C17 C22 C23 78.68(14) . .
C18 C17 C22 C24 -44.20(16) . .
C18 C19 C20 C21 0.7(2) . .
C19 C20 C21 C16 -2.72(19) . .
C19 C20 C21 C25 175.62(12) . .
C20 C21 C25 C26 -74.32(15) . .
C20 C21 C25 C27 49.33(16) . .
C21 C16 C17 C18 -0.34(17) . .
C21 C16 C17 C22 177.30(11) . .
C22 C17 C18 C19 -179.59(12) . .
C28 C29 C30 C28 0.41(19) . 3_666
C30 C28 C29 C30 -0.42(19) 3_666 .
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
-3.0008 0.0006 5.0018 0.1918 0.1142 -0.0530
3.0008 -0.0006 -5.0018 -0.1918 -0.1142 0.0530
2.0005 4.9994 -2.0030 -0.2150 0.1981 0.1443
-2.0005 -4.9994 2.0030 0.2150 -0.1981 -0.1443
3.9987 0.0012 4.9982 -0.1010 0.1113 -0.2577
-3.9987 -0.0012 -4.9982 0.1010 -0.1113 0.2577
5.0006 -1.0004 -5.0025 -0.2546 -0.1638 -0.0348
-1.0008 3.0005 4.9997 0.0453 0.2598 -0.0236
