#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:15:19 +0300 (Fri, 05 May 2023) $
#$Revision: 283448 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/92/7159229.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_7159229
loop_
_publ_author_name
'Komogortsev, Andrey N.'
'Lichitskii, Boris V.'
'Milyutin, Constantine V.'
'Melekhina, Valeriya G.'
_publ_section_title
;
 Photochemical synthesis and ring-chain-ring tautomerism of
 benzo[4,5]imidazo[1,2-a]cyclopenta[e]pyridines.
;
_journal_issue                   13
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2720
_journal_page_last               2728
_journal_paper_doi               10.1039/d3ob00273j
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C25 H24 N4 O2'
_chemical_formula_sum            'C25 H24 N4 O2'
_chemical_formula_weight         412.48
_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   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-02-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-12-29 deposited with the CCDC.	2023-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.5529(13)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.1847(2)
_cell_length_b                   9.88774(11)
_cell_length_c                   27.3603(4)
_cell_measurement_reflns_used    21523
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      79.1870
_cell_measurement_theta_min      3.3510
_cell_volume                     4715.65(11)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -90.00 -64.80   0.40    0.26    --  -48.51-147.00 -31.00   63
  2  ω    -69.00 -43.00   0.40    0.26    --  -48.51 147.00  18.00   65
  3  ω    -74.00 -48.80   0.40    0.26    --  -48.51 125.00-147.00   63
  4  ω     46.00  71.20   0.40    0.26    --   48.51-125.00 134.00   63
  5  ω     48.80 108.00   0.40    0.26    --   48.51-147.00 -31.00  148
  6  ω    -76.00 -50.80   0.40    0.69    --  -90.00 125.00-147.00   63
  7  ω   -141.00-115.80   0.40    0.69    --  -90.00-125.00 134.00   63
  8  ω    -87.00 -61.80   0.40    0.69    --  -90.00 147.00  18.00   63
  9  ω     80.00 106.00   0.40    0.69    --  111.50 147.00  18.00   65
 10  ω     99.00 157.00   0.40    0.69    --  111.50 125.00-147.00  145
 11  ω     88.00 126.00   0.40    0.69    --  111.50-147.00 -31.00   95
 12  ω     70.00 110.00   0.40    0.69    --  111.50-125.00 134.00  100
 13  ω   -119.00 -75.80   0.40    0.26    --  -48.51-125.00-150.00  108
 14  ω   -120.00 -28.80   0.40    0.26    --  -48.51 -77.00 120.00  228
 15  ω   -120.00 -94.80   0.40    0.26    --  -48.51-125.00 -60.00   63
 16  ω    -25.00  25.00   0.40    0.26    --  -48.51  19.00-150.00  125
 17  ω    -11.20  26.00   0.40    0.26    --  -48.51  19.00 150.00   93
 18  ω    -12.00  23.20   0.40    0.26    --   48.51 -38.00-120.00   88
 19  ω    -50.00 -18.80   0.40    0.69    --  -90.00  45.00  60.00   78
 20  ω     72.00 104.00   0.40    0.69    --  111.50 -95.00 -28.97   80
 21  ω     46.00  74.00   0.40    0.69    --  111.50 -85.00-154.10   70
 22  ω     41.00  69.00   0.40    0.69    --  111.50 -95.00 -28.97   70
 23  ω    103.00 176.20   0.40    0.69    --  111.50  45.00 -30.00  183
 24  ω     42.00 106.00   0.40    0.69    --  111.50-105.00 -45.54  160
 25  ω     41.00  66.20   0.40    0.69    --  111.50 -61.00  90.00   63
 26  ω     40.00  66.00   0.40    0.69    --  111.50 -57.00 -27.00   65
 27  ω     41.00  78.20   0.40    0.69    --  111.50 -77.00 150.00   93
 28  ω     46.00 103.20   0.40    0.69    --  111.50-102.00 126.30  143
 29  ω     92.00 125.20   0.40    0.69    --  111.50-145.00 128.42   83
 30  ω     99.00 169.00   0.40    0.69    --  111.50 125.00 150.00  175
 31  ω     80.00 118.00   0.40    0.69    --  111.50-134.00-101.61   95
 32  ω     40.00  72.00   0.40    0.69    --  111.50 -77.00 -30.00   80
 33  ω     41.00  70.20   0.40    0.69    --  111.50-125.00 150.00   73
 34  ω     89.00 116.20   0.40    0.69    --  111.50 -85.00-154.10   68
 35  ω    114.00 152.00   0.40    0.69    --  111.50  77.00 150.00   95
 36  ω    104.00 140.00   0.40    0.69    --  111.50  45.00   0.00   90
 37  ω    144.00 170.00   0.40    0.69    --  111.50  45.00   0.00   65
 38  ω     40.00 106.00   0.40    0.69    --  111.50-119.00 -42.05  165
 39  ω     41.00  74.20   0.40    0.69    --  111.50-125.00-180.00   83
 40  ω     44.00  85.20   0.40    0.69    --  111.50 -77.00-150.00  103
 41  ω    143.00 169.00   0.40    0.69    --  111.50  30.00 120.00   65
 42  ω     53.00  78.20   0.40    0.69    --  111.50-145.00 128.42   63
 43  ω    103.00 130.20   0.40    0.69    --  111.50  45.00  30.00   68
 44  ω     95.00 157.00   0.40    0.69    --  111.50 125.00   0.00  155
 45  ω     41.00  70.20   0.40    0.69    --  111.50 -61.00  30.00   73
 46  ω     73.00 101.00   0.40    0.69    --  111.50 -95.00-180.00   70
 47  ω    135.00 177.00   0.40    0.69    --  111.50 125.00 120.00  105
 48  ω     47.00  76.20   0.40    0.69    --  111.50 -77.00 -60.00   73
 49  ω    116.80 178.00   0.40    0.69    --  111.50  77.00-150.00  153
 50  ω    141.00 166.20   0.40    0.69    --  111.50  15.00 150.00   63
 51  ω    130.00 156.00   0.40    0.69    --  111.50  45.00 120.00   65
 52  ω     66.00 102.00   0.40    0.69    --  111.50 -77.00  30.00   90
 53  ω     42.00  70.00   0.40    0.69    --  111.50-125.00 -60.00   70
 54  ω     70.00 111.20   0.40    0.69    --  111.50 -81.00 -93.69  103
 55  ω    122.00 162.00   0.40    0.69    --  111.50  30.00  30.00  100
 56  ω     42.00  69.20   0.40    0.69    --  111.50 -61.00   0.00   68
 57  ω     42.00  69.20   0.40    0.69    --  111.50 -61.00  60.00   68
 58  ω     79.00 105.00   0.40    0.69    --  111.50-107.00   4.97   65
;
_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      0.0053788000
_diffrn_orient_matrix_UB_12      -0.1542623000
_diffrn_orient_matrix_UB_13      0.0081221000
_diffrn_orient_matrix_UB_21      -0.0114660000
_diffrn_orient_matrix_UB_22      0.0183202000
_diffrn_orient_matrix_UB_23      0.0532610000
_diffrn_orient_matrix_UB_31      -0.0874810000
_diffrn_orient_matrix_UB_32      -0.0119180000
_diffrn_orient_matrix_UB_33      -0.0233790000
_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  0.0370
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            32398
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.678
_diffrn_reflns_theta_min         3.370
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.604
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.877
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.00065(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         5013
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0563
_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)+(0.0481P)²+9.2106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1413
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4797
_reflns_number_total             5013
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00273j2.cif
_cod_data_source_block           KOKBMIMUVQHI
_cod_depositor_comments
'Adding full bibliography for 7159223--7159229.cif.'
_cod_database_code               7159229
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C25 H24 N3 O3'
_chemical_oxdiff_usercomment     KOKBMIMUVQHI
_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   0.942
_shelx_estimated_absorpt_t_min   0.849
_reflns_odcompleteness_completeness 96.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.50
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O1-H1
 0.85 with sigma of 0.02
;
_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 6.161
_oxdiff_exptl_absorpt_empirical_full_min 0.632
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 0.42891(9) 0.83739(13) 0.63706(6) 0.0368(3) Uani 1 1 d D . . . .
H1 H 0.4484(15) 0.864(3) 0.6125(9) 0.055 Uiso 1 1 d D U . . .
O2 O 0.24244(7) 0.50922(13) 0.67815(5) 0.0319(3) Uani 1 1 d . . . . .
N1 N 0.50410(9) 0.70026(16) 0.80988(7) 0.0318(4) Uani 1 1 d . . . . .
N2 N 0.53633(9) 0.67009(15) 0.73735(6) 0.0289(3) Uani 1 1 d . . . . .
N3 N 0.49973(9) 0.41767(15) 0.58039(6) 0.0281(3) Uani 1 1 d . . . . .
N4 N 0.38260(9) 0.61931(16) 0.55930(6) 0.0317(4) Uani 1 1 d . . . . .
C1 C 0.44163(10) 0.69910(17) 0.64924(8) 0.0280(4) Uani 1 1 d . . . . .
C2 C 0.38137(10) 0.66040(17) 0.67819(7) 0.0269(4) Uani 1 1 d . . . . .
C3 C 0.40346(11) 0.74404(19) 0.72771(8) 0.0302(4) Uani 1 1 d . . . . .
H3A H 0.3663(13) 0.734(2) 0.7488(9) 0.033(6) Uiso 1 1 d . . . . .
H3B H 0.4010(13) 0.841(2) 0.7188(9) 0.031(6) Uiso 1 1 d . . . . .
C4 C 0.48102(10) 0.70614(18) 0.75984(8) 0.0291(4) Uani 1 1 d . . . . .
C5 C 0.52812(10) 0.67131(18) 0.68225(8) 0.0286(4) Uani 1 1 d . . . . .
C6 C 0.55009(10) 0.5306(2) 0.66489(8) 0.0304(4) Uani 1 1 d . . . . .
H6A H 0.5424(13) 0.457(3) 0.6888(9) 0.037(6) Uiso 1 1 d . . . . .
H6B H 0.6049(13) 0.527(2) 0.6646(9) 0.034(6) Uiso 1 1 d . . . . .
C7 C 0.49545(10) 0.51208(17) 0.61310(7) 0.0263(4) Uani 1 1 d . . . . .
C8 C 0.43569(10) 0.61029(18) 0.60299(7) 0.0274(4) Uani 1 1 d . . . . .
C9 C 0.58060(12) 0.7814(2) 0.67153(9) 0.0368(5) Uani 1 1 d . . . . .
H9A H 0.6370(16) 0.757(3) 0.6885(10) 0.047(7) Uiso 1 1 d . . . . .
H9B H 0.5701(13) 0.787(3) 0.6321(10) 0.040(6) Uiso 1 1 d . . . . .
H9C H 0.5685(14) 0.875(3) 0.6845(10) 0.043(7) Uiso 1 1 d . . . . .
C10 C 0.58076(11) 0.66045(18) 0.82184(8) 0.0312(4) Uani 1 1 d . . . . .
C11 C 0.63415(12) 0.6431(2) 0.86941(9) 0.0363(4) Uani 1 1 d . . . . .
H11 H 0.6188(19) 0.659(3) 0.8994(13) 0.073(10) Uiso 1 1 d . . . . .
C12 C 0.70746(12) 0.6020(2) 0.87066(9) 0.0385(5) Uani 1 1 d . . . . .
H12 H 0.7478(14) 0.592(3) 0.9050(10) 0.041(6) Uiso 1 1 d . . . . .
C13 C 0.72690(11) 0.5769(2) 0.82548(9) 0.0363(5) Uani 1 1 d . . . . .
H13 H 0.7806(13) 0.545(2) 0.8282(8) 0.033(6) Uiso 1 1 d . . . . .
C14 C 0.67511(11) 0.59455(19) 0.77779(9) 0.0332(4) Uani 1 1 d . . . . .
H14 H 0.6892(14) 0.575(3) 0.7466(10) 0.042(7) Uiso 1 1 d . . . . .
C15 C 0.60188(11) 0.63864(18) 0.77689(8) 0.0300(4) Uani 1 1 d . . . . .
C16 C 0.44299(11) 0.41876(19) 0.53536(8) 0.0296(4) Uani 1 1 d . . . . .
C17 C 0.43956(12) 0.3147(2) 0.49955(8) 0.0339(4) Uani 1 1 d . . . . .
H17 H 0.4810(14) 0.241(3) 0.5099(9) 0.042(7) Uiso 1 1 d . . . . .
C18 C 0.38182(14) 0.3124(3) 0.45479(9) 0.0427(5) Uani 1 1 d . . . . .
H18 H 0.3806(15) 0.237(3) 0.4317(10) 0.047(7) Uiso 1 1 d . . . . .
C19 C 0.32698(14) 0.4174(3) 0.44267(9) 0.0482(6) Uani 1 1 d . . . . .
H19 H 0.2864(16) 0.425(3) 0.4088(11) 0.056(8) Uiso 1 1 d . . . . .
C20 C 0.32959(13) 0.5205(3) 0.47638(9) 0.0457(5) Uani 1 1 d . . . . .
H20 H 0.2878(15) 0.590(3) 0.4683(9) 0.044(7) Uiso 1 1 d . . . . .
C21 C 0.38555(11) 0.5219(2) 0.52399(8) 0.0325(4) Uani 1 1 d . . . . .
C22 C 0.30036(11) 0.69945(19) 0.64575(8) 0.0300(4) Uani 1 1 d . . . . .
H22A H 0.2928(14) 0.659(3) 0.6120(10) 0.039(6) Uiso 1 1 d . . . . .
H22B H 0.2959(13) 0.799(3) 0.6414(9) 0.038(6) Uiso 1 1 d . . . . .
C23 C 0.23879(11) 0.6517(2) 0.66963(9) 0.0330(4) Uani 1 1 d . . . . .
H23A H 0.2427(13) 0.700(2) 0.7034(9) 0.033(6) Uiso 1 1 d . . . . .
H23B H 0.1894(13) 0.669(2) 0.6462(9) 0.032(6) Uiso 1 1 d . . . . .
C24 C 0.31519(10) 0.47035(19) 0.71136(8) 0.0303(4) Uani 1 1 d . . . . .
H24A H 0.3134(12) 0.366(2) 0.7149(8) 0.028(5) Uiso 1 1 d . . . . .
H24B H 0.3240(13) 0.514(2) 0.7468(9) 0.036(6) Uiso 1 1 d . . . . .
C25 C 0.38067(10) 0.50747(18) 0.68945(8) 0.0267(4) Uani 1 1 d . . . . .
H25A H 0.3720(12) 0.456(2) 0.6569(9) 0.028(5) Uiso 1 1 d . . . . .
H25B H 0.4292(13) 0.479(2) 0.7140(9) 0.032(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 0.0181 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 -1 0.0819
0 -1 1 0.0800
0 0 -1 0.0374
0 0 1 0.0579
-2 0 1 0.1266
2 0 -1 0.1479
0 -1 -2 0.0637
0 2 1 0.0943
-1 0 2 0.0943
-1 0 -2 0.0817
1 0 -2 0.1112
1 0 2 0.1129
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
C1 O1 H1 113.0(19) . . ?
C23 O2 C24 111.19(14) . . ?
C4 N1 C10 104.96(16) . . ?
C4 N2 C5 125.85(16) . . ?
C4 N2 C15 106.50(16) . . ?
C15 N2 C5 127.59(16) . . ?
C7 N3 C16 115.75(16) . . ?
C8 N4 C21 115.32(16) . . ?
O1 C1 C2 105.32(14) . . ?
O1 C1 C5 111.63(15) . . ?
O1 C1 C8 113.32(16) . . ?
C2 C1 C5 112.86(15) . . ?
C8 C1 C2 112.64(14) . . ?
C8 C1 C5 101.32(14) . . ?
C3 C2 C1 105.56(14) . . ?
C3 C2 C25 111.43(16) . . ?
C22 C2 C1 109.82(16) . . ?
C22 C2 C3 109.88(15) . . ?
C22 C2 C25 107.47(14) . . ?
C25 C2 C1 112.68(14) . . ?
C2 C3 H3A 113.6(13) . . ?
C2 C3 H3B 108.9(13) . . ?
H3A C3 H3B 104.1(18) . . ?
C4 C3 C2 110.60(15) . . ?
C4 C3 H3A 108.4(13) . . ?
C4 C3 H3B 111.2(13) . . ?
N1 C4 N2 113.57(17) . . ?
N1 C4 C3 126.64(18) . . ?
N2 C4 C3 119.78(18) . . ?
N2 C5 C1 112.11(15) . . ?
N2 C5 C6 110.17(16) . . ?
N2 C5 C9 108.38(15) . . ?
C6 C5 C1 106.12(14) . . ?
C9 C5 C1 109.66(16) . . ?
C9 C5 C6 110.41(16) . . ?
C5 C6 H6A 110.4(14) . . ?
C5 C6 H6B 112.1(14) . . ?
H6A C6 H6B 107.5(19) . . ?
C7 C6 C5 103.87(15) . . ?
C7 C6 H6A 110.4(14) . . ?
C7 C6 H6B 112.6(13) . . ?
N3 C7 C6 125.64(16) . . ?
N3 C7 C8 122.90(17) . . ?
C8 C7 C6 111.45(16) . . ?
N4 C8 C1 125.50(16) . . ?
N4 C8 C7 123.20(17) . . ?
C7 C8 C1 111.29(16) . . ?
C5 C9 H9A 110.3(15) . . ?
C5 C9 H9B 107.1(14) . . ?
C5 C9 H9C 111.4(14) . . ?
H9A C9 H9B 110(2) . . ?
H9A C9 H9C 110(2) . . ?
H9B C9 H9C 108(2) . . ?
N1 C10 C15 110.00(17) . . ?
C11 C10 N1 129.57(19) . . ?
C11 C10 C15 120.43(19) . . ?
C10 C11 H11 119(2) . . ?
C12 C11 C10 117.9(2) . . ?
C12 C11 H11 123(2) . . ?
C11 C12 H12 119.1(14) . . ?
C11 C12 C13 120.9(2) . . ?
C13 C12 H12 120.0(14) . . ?
C12 C13 H13 118.1(13) . . ?
C14 C13 C12 122.3(2) . . ?
C14 C13 H13 119.6(13) . . ?
C13 C14 H14 121.3(15) . . ?
C13 C14 C15 116.5(2) . . ?
C15 C14 H14 122.2(15) . . ?
N2 C15 C10 104.95(16) . . ?
C14 C15 N2 133.05(19) . . ?
C14 C15 C10 122.01(19) . . ?
N3 C16 C17 119.64(17) . . ?
N3 C16 C21 121.37(17) . . ?
C17 C16 C21 118.98(18) . . ?
C16 C17 H17 116.1(14) . . ?
C18 C17 C16 120.4(2) . . ?
C18 C17 H17 123.5(14) . . ?
C17 C18 H18 117.7(16) . . ?
C17 C18 C19 120.6(2) . . ?
C19 C18 H18 121.7(16) . . ?
C18 C19 H19 123.4(17) . . ?
C20 C19 C18 120.2(2) . . ?
C20 C19 H19 116.3(17) . . ?
C19 C20 H20 119.1(15) . . ?
C19 C20 C21 120.7(2) . . ?
C21 C20 H20 120.0(15) . . ?
N4 C21 C16 121.25(18) . . ?
N4 C21 C20 119.67(19) . . ?
C20 C21 C16 119.05(19) . . ?
C2 C22 H22A 107.2(14) . . ?
C2 C22 H22B 110.5(14) . . ?
H22A C22 H22B 108(2) . . ?
C23 C22 C2 112.03(16) . . ?
C23 C22 H22A 110.8(14) . . ?
C23 C22 H22B 108.4(14) . . ?
O2 C23 C22 111.77(15) . . ?
O2 C23 H23A 109.1(13) . . ?
O2 C23 H23B 105.9(14) . . ?
C22 C23 H23A 111.8(13) . . ?
C22 C23 H23B 108.8(14) . . ?
H23A C23 H23B 109.3(19) . . ?
O2 C24 H24A 106.2(12) . . ?
O2 C24 H24B 110.7(13) . . ?
O2 C24 C25 111.80(16) . . ?
H24A C24 H24B 109.1(18) . . ?
C25 C24 H24A 109.0(12) . . ?
C25 C24 H24B 109.9(13) . . ?
C2 C25 H25A 109.3(13) . . ?
C2 C25 H25B 111.1(14) . . ?
C24 C25 C2 111.50(15) . . ?
C24 C25 H25A 106.6(12) . . ?
C24 C25 H25B 108.1(13) . . ?
H25A C25 H25B 110.3(18) . . ?
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 H1 0.884(17) . ?
O1 C1 1.411(2) . ?
O2 C23 1.426(2) . ?
O2 C24 1.428(2) . ?
N1 C4 1.314(3) . ?
N1 C10 1.395(3) . ?
N2 C4 1.368(2) . ?
N2 C5 1.472(3) . ?
N2 C15 1.398(3) . ?
N3 C7 1.311(2) . ?
N3 C16 1.363(2) . ?
N4 C8 1.308(3) . ?
N4 C21 1.376(3) . ?
C1 C2 1.571(3) . ?
C1 C5 1.599(3) . ?
C1 C8 1.519(3) . ?
C2 C3 1.540(3) . ?
C2 C22 1.537(3) . ?
C2 C25 1.544(2) . ?
C3 H3A 1.01(2) . ?
C3 H3B 0.99(2) . ?
C3 C4 1.482(3) . ?
C5 C6 1.559(3) . ?
C5 C9 1.530(3) . ?
C6 H6A 1.01(3) . ?
C6 H6B 1.00(2) . ?
C6 C7 1.492(3) . ?
C7 C8 1.425(2) . ?
C9 H9A 1.03(3) . ?
C9 H9B 1.04(3) . ?
C9 H9C 1.04(3) . ?
C10 C11 1.395(3) . ?
C10 C15 1.406(3) . ?
C11 H11 0.95(3) . ?
C11 C12 1.385(3) . ?
C12 H12 1.02(3) . ?
C12 C13 1.401(3) . ?
C13 H13 1.01(2) . ?
C13 C14 1.386(3) . ?
C14 H14 0.98(3) . ?
C14 C15 1.395(3) . ?
C16 C17 1.410(3) . ?
C16 C21 1.429(3) . ?
C17 H17 1.03(3) . ?
C17 C18 1.367(3) . ?
C18 H18 0.97(3) . ?
C18 C19 1.412(4) . ?
C19 H19 1.01(3) . ?
C19 C20 1.366(4) . ?
C20 H20 1.00(3) . ?
C20 C21 1.406(3) . ?
C22 H22A 0.98(3) . ?
C22 H22B 0.99(3) . ?
C22 C23 1.523(3) . ?
C23 H23A 1.03(2) . ?
C23 H23B 0.96(2) . ?
C24 H24A 1.03(2) . ?
C24 H24B 1.03(2) . ?
C24 C25 1.523(3) . ?
C25 H25A 1.00(2) . ?
C25 H25B 0.99(2) . ?
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 C1 C2 C3 -64.53(18) . . . . ?
O1 C1 C2 C22 53.87(19) . . . . ?
O1 C1 C2 C25 173.64(15) . . . . ?
O1 C1 C5 N2 94.86(18) . . . . ?
O1 C1 C5 C6 -144.83(16) . . . . ?
O1 C1 C5 C9 -25.6(2) . . . . ?
O1 C1 C8 N4 -43.7(2) . . . . ?
O1 C1 C8 C7 137.17(16) . . . . ?
O2 C24 C25 C2 57.2(2) . . . . ?
N1 C10 C11 C12 179.84(19) . . . . ?
N1 C10 C15 N2 1.6(2) . . . . ?
N1 C10 C15 C14 -178.31(16) . . . . ?
N2 C5 C6 C7 143.73(15) . . . . ?
N3 C7 C8 N4 -3.9(3) . . . . ?
N3 C7 C8 C1 175.21(16) . . . . ?
N3 C16 C17 C18 178.25(19) . . . . ?
N3 C16 C21 N4 -4.0(3) . . . . ?
N3 C16 C21 C20 178.20(19) . . . . ?
C1 C2 C3 C4 -62.52(19) . . . . ?
C1 C2 C22 C23 174.37(15) . . . . ?
C1 C2 C25 C24 -172.77(16) . . . . ?
C1 C5 C6 C7 22.16(19) . . . . ?
C2 C1 C5 N2 -23.5(2) . . . . ?
C2 C1 C5 C6 96.77(17) . . . . ?
C2 C1 C5 C9 -143.97(16) . . . . ?
C2 C1 C8 N4 75.7(2) . . . . ?
C2 C1 C8 C7 -103.40(17) . . . . ?
C2 C3 C4 N1 -144.17(18) . . . . ?
C2 C3 C4 N2 34.5(2) . . . . ?
C2 C22 C23 O2 -56.6(2) . . . . ?
C3 C2 C22 C23 -69.9(2) . . . . ?
C3 C2 C25 C24 68.8(2) . . . . ?
C4 N1 C10 C11 177.34(19) . . . . ?
C4 N1 C10 C15 -1.8(2) . . . . ?
C4 N2 C5 C1 -8.6(2) . . . . ?
C4 N2 C5 C6 -126.54(18) . . . . ?
C4 N2 C5 C9 112.56(19) . . . . ?
C4 N2 C15 C10 -0.75(19) . . . . ?
C4 N2 C15 C14 179.16(19) . . . . ?
C5 N2 C4 N1 -177.79(16) . . . . ?
C5 N2 C4 C3 3.4(3) . . . . ?
C5 N2 C15 C10 176.57(16) . . . . ?
C5 N2 C15 C14 -3.5(3) . . . . ?
C5 C1 C2 C3 57.49(18) . . . . ?
C5 C1 C2 C22 175.89(14) . . . . ?
C5 C1 C2 C25 -64.3(2) . . . . ?
C5 C1 C8 N4 -163.44(17) . . . . ?
C5 C1 C8 C7 17.45(19) . . . . ?
C5 C6 C7 N3 168.95(17) . . . . ?
C5 C6 C7 C8 -11.8(2) . . . . ?
C6 C7 C8 N4 176.79(17) . . . . ?
C6 C7 C8 C1 -4.1(2) . . . . ?
C7 N3 C16 C17 -175.03(17) . . . . ?
C7 N3 C16 C21 3.6(3) . . . . ?
C8 N4 C21 C16 0.3(3) . . . . ?
C8 N4 C21 C20 178.10(19) . . . . ?
C8 C1 C2 C3 171.49(15) . . . . ?
C8 C1 C2 C22 -70.11(19) . . . . ?
C8 C1 C2 C25 49.7(2) . . . . ?
C8 C1 C5 N2 -144.23(15) . . . . ?
C8 C1 C5 C6 -23.92(18) . . . . ?
C8 C1 C5 C9 95.33(17) . . . . ?
C9 C5 C6 C7 -96.60(18) . . . . ?
C10 N1 C4 N2 1.4(2) . . . . ?
C10 N1 C4 C3 -179.88(17) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C10 C15 N2 -177.67(16) . . . . ?
C11 C10 C15 C14 2.4(3) . . . . ?
C11 C12 C13 C14 1.5(3) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 N2 178.35(18) . . . . ?
C13 C14 C15 C10 -1.8(3) . . . . ?
C15 N2 C4 N1 -0.4(2) . . . . ?
C15 N2 C4 C3 -179.24(16) . . . . ?
C15 N2 C5 C1 174.56(16) . . . . ?
C15 N2 C5 C6 56.6(2) . . . . ?
C15 N2 C5 C9 -64.3(2) . . . . ?
C15 C10 C11 C12 -1.0(3) . . . . ?
C16 N3 C7 C6 179.30(17) . . . . ?
C16 N3 C7 C8 0.1(3) . . . . ?
C16 C17 C18 C19 3.1(3) . . . . ?
C17 C16 C21 N4 174.60(18) . . . . ?
C17 C16 C21 C20 -3.2(3) . . . . ?
C17 C18 C19 C20 -2.2(4) . . . . ?
C18 C19 C20 C21 -1.5(4) . . . . ?
C19 C20 C21 N4 -173.7(2) . . . . ?
C19 C20 C21 C16 4.1(3) . . . . ?
C21 N4 C8 C1 -175.59(17) . . . . ?
C21 N4 C8 C7 3.4(3) . . . . ?
C21 C16 C17 C18 -0.4(3) . . . . ?
C22 C2 C3 C4 179.13(16) . . . . ?
C22 C2 C25 C24 -51.7(2) . . . . ?
C23 O2 C24 C25 -60.1(2) . . . . ?
C24 O2 C23 C22 59.6(2) . . . . ?
C25 C2 C3 C4 60.1(2) . . . . ?
C25 C2 C22 C23 51.5(2) . . . . ?
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
0.0005 1.0001 -0.9961 -0.1624 -0.0347 0.0113
-0.0005 -1.0001 0.9961 0.1624 0.0347 -0.0113
0.0001 0.0003 -0.9982 -0.0082 -0.0532 0.0233
-0.0001 -0.0003 0.9982 0.0082 0.0532 -0.0233
-1.9979 0.0001 0.9923 -0.0027 0.0758 0.1516
1.9979 -0.0001 -0.9923 0.0027 -0.0758 -0.1516
-0.0001 -0.9992 -1.9985 0.1379 -0.1247 0.0586
0.0007 1.9993 1.0025 -0.3003 0.0900 -0.0473
-0.9991 -0.0004 1.9935 0.0109 0.1176 0.0408
-0.9986 0.0008 -1.9993 -0.0217 -0.0950 0.1341
0.9991 0.0004 -1.9935 -0.0109 -0.1176 -0.0408
0.9986 -0.0008 1.9993 0.0217 0.0950 -0.1341
