#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:15:19 +0300 (Fri, 05 May 2023) $
#$Revision: 283448 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/92/7159224.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_7159224
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         'C21 H20 N2 O4'
_chemical_formula_sum            'C21 H20 N2 O4'
_chemical_formula_weight         364.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                107.8011(13)
_cell_angle_beta                 96.7797(9)
_cell_angle_gamma                98.0759(10)
_cell_formula_units_Z            2
_cell_length_a                   7.48251(7)
_cell_length_b                   8.97191(13)
_cell_length_c                   13.67021(19)
_cell_measurement_reflns_used    14898
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.0000
_cell_measurement_theta_min      3.4500
_cell_volume                     852.40(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_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      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 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    133.00 159.00   0.40    0.33    --  111.50  45.00-180.00   65
  2  ω    101.00 177.00   0.40    0.33    --  111.50  45.00-120.00  190
  3  ω    149.00 175.00   0.40    0.33    --  111.50  45.00 -90.00   65
  4  ω    102.00 142.00   0.40    0.33    --  111.50  61.00  30.00  100
  5  ω    101.00 152.20   0.40    0.33    --  111.50  45.00  90.00  128
  6  ω    118.00 153.20   0.40    0.33    --  111.50  45.00 150.00   88
  7  ω    101.00 177.00   0.40    0.33    --  111.50  45.00 120.00  190
  8  ω    101.00 177.00   0.40    0.33    --  111.50  15.00  60.00  190
  9  ω    103.00 175.00   0.40    0.33    --  111.50  21.00  -8.03  180
 10  ω    101.00 177.00   0.40    0.33    --  111.50  15.00-120.00  190
 11  ω    124.00 150.00   0.40    0.33    --  111.50  15.00-150.00   65
 12  ω    -63.00  23.00   0.40    0.08    --  -48.76  57.00  60.00  215
 13  ω    -26.00  26.00   0.40    0.08    --  -48.76  19.00-180.00  130
 14  ω    -26.00  26.00   0.40    0.08    --  -48.76  19.00 -90.00  130
 15  ω    -51.00 -19.00   0.40    0.33    --  -90.00  45.00   0.00   80
 16  ω    -43.00  23.00   0.40    0.08    --  -48.76  38.00 150.00  165
 17  ω     40.00 110.00   0.40    0.33    --  111.50-125.00 -60.00  175
 18  ω     82.00 108.00   0.40    0.33    --  111.50-119.00  42.62   65
 19  ω     40.00 110.00   0.40    0.33    --  111.50-125.00   0.00  175
 20  ω     44.00  70.00   0.40    0.33    --  111.50-119.00  42.62   65
 21  ω     40.00  86.00   0.40    0.33    --  111.50-125.00 -30.00  115
 22  ω     43.00  68.20   0.40    0.33    --  111.50-104.00 -64.50   63
 23  ω     40.00 108.00   0.40    0.33    --  111.50-110.00 -24.00  170
 24  ω     63.00 103.00   0.40    0.33    --  111.50-103.00  31.48  100
 25  ω     23.00  87.00   0.40    0.08    --   48.76-110.00 -24.00  160
 26  ω     40.00 104.00   0.40    0.33    --  111.50 -98.00  61.25  160
 27  ω     72.00  98.00   0.40    0.33    --  111.50-104.00 -64.50   65
 28  ω     61.00  92.20   0.40    0.33    --  111.50 -95.00-120.00   78
 29  ω     40.00 110.00   0.40    0.33    --  111.50-125.00-180.00  175
 30  ω     76.00 102.00   0.40    0.33    --  111.50-102.00-168.32   65
 31  ω     84.00 109.20   0.40    0.33    --  111.50-125.00 -90.00   63
 32  ω     40.00 104.00   0.40    0.33    --  111.50 -95.00-180.00  160
 33  ω     44.00  78.00   0.40    0.33    --  111.50 -95.00   0.00   85
 34  ω     76.00 103.20   0.40    0.33    --  111.50 -95.00 -30.00   68
 35  ω     40.00 104.00   0.40    0.33    --  111.50 -95.00  30.00  160
 36  ω     40.00 104.00   0.40    0.33    --  111.50 -95.00  60.00  160
 37  ω     45.00 103.00   0.40    0.33    --  111.50 -95.00 150.00  145
 38  ω     40.00  76.00   0.40    0.33    --  111.50 -95.00  90.00   90
 39  ω     42.00  69.20   0.40    0.33    --  111.50 -85.00  64.61   68
 40  ω     40.00  65.20   0.40    0.33    --  111.50 -87.00 -83.52   63
 41  ω     40.00 104.00   0.40    0.33    --  111.50 -95.00-150.00  160
 42  ω    103.00 129.00   0.40    0.33    --  111.50 -87.00 -83.52   65
 43  ω     84.00 116.00   0.40    0.33    --  111.50 -85.00  64.61   80
 44  ω     59.00 104.20   0.40    0.33    --  111.50 -77.00  60.00  113
 45  ω     65.00  99.00   0.40    0.33    --  111.50 -77.00 150.00   85
 46  ω     50.00  94.00   0.40    0.33    --  111.50 -77.00 -30.00  110
 47  ω     40.00  70.00   0.40    0.33    --  111.50 -61.00-180.00   75
 48  ω     57.00  99.00   0.40    0.33    --  111.50 -77.00-180.00  105
 49  ω     45.00  71.00   0.40    0.33    --  111.50 -77.00 -90.00   65
 50  ω    -25.00  25.00   0.40    0.08    --   48.76 -19.00 -90.00  125
 51  ω     44.00  69.20   0.40    0.33    --  111.50 -61.00 120.00   63
 52  ω     42.00  70.00   0.40    0.33    --  111.50 -61.00 150.00   70
 53  ω     95.00 177.00   0.40    0.33    --  111.50 125.00 -60.00  205
 54  ω    138.00 170.00   0.40    0.33    --  111.50 125.00   0.00   80
 55  ω    102.00 127.20   0.40    0.33    --  111.50 125.00   0.00   63
 56  ω    122.00 148.00   0.40    0.33    --  111.50 125.00-120.00   65
 57  ω     96.00 121.20   0.40    0.33    --  111.50 125.00-120.00   63
 58  ω     97.00 151.00   0.40    0.33    --  111.50 125.00-150.00  135
 59  ω    124.00 170.00   0.40    0.33    --  111.50 125.00 -90.00  115
 60  ω    103.00 177.00   0.40    0.33    --  111.50 110.00  70.00  185
 61  ω    131.00 167.00   0.40    0.33    --  111.50 125.00 150.00   90
 62  ω   -161.00 -77.00   0.40    0.33    --  -90.00 -56.00  49.09  210
 63  ω   -121.00 -73.00   0.40    0.08    --  -48.76-125.00 150.00  120
 64  ω   -121.00 -73.00   0.40    0.08    --  -48.76-125.00  30.00  120
 65  ω   -161.00 -83.00   0.40    0.33    --  -90.00-110.00 -24.00  195
 66  ω    -82.00 -18.00   0.40    0.33    --  -90.00 110.00  70.00  160
 67  ω    -82.00  -2.00   0.40    0.08    --  -48.76 110.00  70.00  200
;
_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      -0.0026200000
_diffrn_orient_matrix_UB_12      -0.1211283000
_diffrn_orient_matrix_UB_13      -0.1081933000
_diffrn_orient_matrix_UB_21      0.0253528000
_diffrn_orient_matrix_UB_22      0.1369548000
_diffrn_orient_matrix_UB_23      -0.0458929000
_diffrn_orient_matrix_UB_31      0.2095069000
_diffrn_orient_matrix_UB_32      0.0164490000
_diffrn_orient_matrix_UB_33      0.0248681000
_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  0.0308
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18947
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.456
_diffrn_reflns_theta_min         3.446
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.813
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.845
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
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            'clear colourless'
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0025(7)
_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   1.034
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         3679
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0377
_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)+(0.0621P)²+0.3236P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1049
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3503
_reflns_number_total             3679
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00273j2.cif
_cod_data_source_block           C6UV-CDI
_cod_depositor_comments
'Adding full bibliography for 7159223--7159229.cif.'
_cod_database_code               7159224
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C21 H20 N2 O4'
_chemical_oxdiff_usercomment     C6UV-CDI
_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   0.938
_shelx_estimated_absorpt_t_min   0.804
_reflns_odcompleteness_completeness 98.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.50
_olex2_refinement_description
;
;
_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 1.307
_oxdiff_exptl_absorpt_empirical_full_min 0.650
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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 0.30972(11) 0.14207(9) 0.56007(6) 0.01931(19) Uani 1 1 d . . . . .
O2 O 0.16873(11) 0.34055(9) 0.54728(6) 0.01853(19) Uani 1 1 d . . . . .
O3 O 0.08467(12) 0.09833(10) 0.42475(7) 0.0246(2) Uani 1 1 d . . . . .
O4 O 0.39287(13) 0.67360(10) 0.63279(8) 0.0282(2) Uani 1 1 d . . . . .
N1 N 0.05468(13) 0.41373(11) 0.86205(7) 0.0181(2) Uani 1 1 d . . . . .
N2 N 0.18665(12) 0.45191(11) 0.72947(7) 0.0161(2) Uani 1 1 d . . . . .
C1 C 0.17933(15) 0.18475(13) 0.50330(9) 0.0186(2) Uani 1 1 d . . . . .
C2 C 0.29081(15) 0.40976(13) 0.64716(8) 0.0164(2) Uani 1 1 d . . . . .
C3 C 0.40585(15) 0.27725(12) 0.64931(9) 0.0169(2) Uani 1 1 d . . . . .
C4 C 0.42969(16) 0.54881(13) 0.63769(9) 0.0196(2) Uani 1 1 d . . . . .
C5 C 0.59995(16) 0.49167(14) 0.62455(9) 0.0219(2) Uani 1 1 d . . . . .
H5 H 0.703(2) 0.556(2) 0.6130(13) 0.030(4) Uiso 1 1 d . . . . .
C6 C 0.58828(15) 0.34091(14) 0.62363(9) 0.0200(2) Uani 1 1 d . . . . .
C7 C 0.73029(17) 0.24191(16) 0.59561(11) 0.0266(3) Uani 1 1 d . . . . .
H7A H 0.818(3) 0.295(3) 0.5609(17) 0.051(5) Uiso 1 1 d . . . . .
H7B H 0.672(2) 0.136(2) 0.5473(14) 0.036(4) Uiso 1 1 d . . . . .
H7C H 0.800(2) 0.234(2) 0.6591(15) 0.036(4) Uiso 1 1 d . . . . .
C8 C 0.41539(15) 0.22380(13) 0.74724(9) 0.0173(2) Uani 1 1 d . . . . .
C9 C 0.21853(15) 0.20422(13) 0.77032(9) 0.0180(2) Uani 1 1 d . . . . .
H9A H 0.140(2) 0.1226(18) 0.7108(12) 0.020(3) Uiso 1 1 d . . . . .
H9B H 0.209(2) 0.171(2) 0.8318(13) 0.026(4) Uiso 1 1 d . . . . .
C10 C 0.14937(14) 0.35594(13) 0.79037(8) 0.0161(2) Uani 1 1 d . . . . .
C11 C 0.02040(15) 0.55622(13) 0.84849(9) 0.0172(2) Uani 1 1 d . . . . .
C12 C -0.07578(16) 0.66415(14) 0.90652(9) 0.0200(2) Uani 1 1 d . . . . .
H12 H -0.120(2) 0.6515(19) 0.9676(13) 0.024(4) Uiso 1 1 d . . . . .
C13 C -0.10037(16) 0.79433(14) 0.87578(10) 0.0217(2) Uani 1 1 d . . . . .
H13 H -0.168(2) 0.874(2) 0.9161(13) 0.030(4) Uiso 1 1 d . . . . .
C14 C -0.03244(16) 0.81478(14) 0.78850(9) 0.0208(2) Uani 1 1 d . . . . .
H14 H -0.056(2) 0.907(2) 0.7668(13) 0.031(4) Uiso 1 1 d . . . . .
C15 C 0.06780(15) 0.71039(13) 0.73133(9) 0.0192(2) Uani 1 1 d . . . . .
H15 H 0.113(2) 0.7237(19) 0.6706(13) 0.023(4) Uiso 1 1 d . . . . .
C16 C 0.09665(14) 0.58184(13) 0.76466(8) 0.0163(2) Uani 1 1 d . . . . .
C17 C 0.47871(16) 0.06189(13) 0.72745(9) 0.0213(2) Uani 1 1 d . . . . .
H17A H 0.387(2) -0.020(2) 0.6721(13) 0.027(4) Uiso 1 1 d . . . . .
H17B H 0.597(2) 0.0633(19) 0.7012(12) 0.024(4) Uiso 1 1 d . . . . .
C18 C 0.50559(17) 0.01587(14) 0.82668(10) 0.0241(3) Uani 1 1 d . . . . .
H18A H 0.384(2) -0.0062(19) 0.8484(12) 0.025(4) Uiso 1 1 d . . . . .
H18B H 0.555(2) -0.086(2) 0.8080(13) 0.031(4) Uiso 1 1 d . . . . .
C19 C 0.63700(18) 0.14628(15) 0.91546(10) 0.0258(3) Uani 1 1 d . . . . .
H19A H 0.651(2) 0.119(2) 0.9813(14) 0.034(4) Uiso 1 1 d . . . . .
H19B H 0.762(2) 0.159(2) 0.8957(13) 0.027(4) Uiso 1 1 d . . . . .
C20 C 0.57244(17) 0.30581(14) 0.93740(9) 0.0229(3) Uani 1 1 d . . . . .
H20A H 0.665(2) 0.390(2) 0.9927(13) 0.029(4) Uiso 1 1 d . . . . .
H20B H 0.455(2) 0.302(2) 0.9672(13) 0.029(4) Uiso 1 1 d . . . . .
C21 C 0.54835(15) 0.35239(13) 0.83849(9) 0.0190(2) Uani 1 1 d . . . . .
H21A H 0.669(2) 0.3655(18) 0.8164(12) 0.020(3) Uiso 1 1 d . . . . .
H21B H 0.506(2) 0.454(2) 0.8535(12) 0.024(4) 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
2 1 0 0.1173
0 2 7 0.0466
0 -2 -7 0.0466
0 0 8 0.0410
0 -3 9 0.0503
4 -2 2 0.1190
0 -6 4 0.0684
0 -4 -5 0.0500
5 -2 -2 0.1209
-5 3 2 0.1541
4 0 -4 0.1122
-4 0 4 0.1423
0 1 -9 0.0369
0 6 -2 0.0783
4 0 2 0.1129
-4 0 -2 0.1424
-4 -2 0 0.1453
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 C3 111.11(8) . . ?
C1 O2 C2 110.56(8) . . ?
C10 N1 C11 104.96(9) . . ?
C10 N2 C2 122.25(9) . . ?
C10 N2 C16 105.91(9) . . ?
C16 N2 C2 131.79(9) . . ?
O1 C1 O2 111.33(9) . . ?
O3 C1 O1 124.80(10) . . ?
O3 C1 O2 123.87(11) . . ?
O2 C2 C3 103.05(8) . . ?
O2 C2 C4 106.62(9) . . ?
N2 C2 O2 110.02(9) . . ?
N2 C2 C3 115.61(9) . . ?
N2 C2 C4 115.74(9) . . ?
C4 C2 C3 104.69(9) . . ?
O1 C3 C2 102.84(8) . . ?
O1 C3 C6 108.54(9) . . ?
O1 C3 C8 107.99(8) . . ?
C6 C3 C2 103.11(9) . . ?
C6 C3 C8 116.54(9) . . ?
C8 C3 C2 116.76(9) . . ?
O4 C4 C2 124.97(11) . . ?
O4 C4 C5 127.97(11) . . ?
C5 C4 C2 106.73(9) . . ?
C4 C5 H5 120.8(10) . . ?
C6 C5 C4 112.55(10) . . ?
C6 C5 H5 126.5(10) . . ?
C5 C6 C3 111.99(10) . . ?
C5 C6 C7 124.87(11) . . ?
C7 C6 C3 123.06(10) . . ?
C6 C7 H7A 108.9(12) . . ?
C6 C7 H7B 109.8(11) . . ?
C6 C7 H7C 110.1(11) . . ?
H7A C7 H7B 109.2(16) . . ?
H7A C7 H7C 108.1(16) . . ?
H7B C7 H7C 110.7(15) . . ?
C9 C8 C3 105.85(9) . . ?
C9 C8 C17 108.51(9) . . ?
C9 C8 C21 111.63(9) . . ?
C17 C8 C3 111.96(9) . . ?
C21 C8 C3 109.17(9) . . ?
C21 C8 C17 109.70(9) . . ?
C8 C9 H9A 108.6(9) . . ?
C8 C9 H9B 112.6(9) . . ?
H9A C9 H9B 107.6(13) . . ?
C10 C9 C8 111.28(9) . . ?
C10 C9 H9A 109.8(9) . . ?
C10 C9 H9B 106.9(10) . . ?
N1 C10 N2 113.78(10) . . ?
N1 C10 C9 126.50(10) . . ?
N2 C10 C9 119.72(10) . . ?
N1 C11 C16 111.00(10) . . ?
C12 C11 N1 127.64(10) . . ?
C12 C11 C16 121.36(10) . . ?
C11 C12 H12 121.6(10) . . ?
C13 C12 C11 117.64(11) . . ?
C13 C12 H12 120.7(10) . . ?
C12 C13 H13 119.6(10) . . ?
C12 C13 C14 120.74(11) . . ?
C14 C13 H13 119.7(10) . . ?
C13 C14 H14 119.1(10) . . ?
C15 C14 C13 122.33(11) . . ?
C15 C14 H14 118.6(10) . . ?
C14 C15 H15 122.2(9) . . ?
C14 C15 C16 116.58(11) . . ?
C16 C15 H15 121.2(9) . . ?
C11 C16 N2 104.24(9) . . ?
C15 C16 N2 134.49(10) . . ?
C15 C16 C11 121.20(10) . . ?
C8 C17 H17A 108.3(10) . . ?
C8 C17 H17B 111.7(9) . . ?
H17A C17 H17B 106.7(13) . . ?
C18 C17 C8 112.18(10) . . ?
C18 C17 H17A 110.8(10) . . ?
C18 C17 H17B 107.0(9) . . ?
C17 C18 H18A 109.4(9) . . ?
C17 C18 H18B 106.8(10) . . ?
H18A C18 H18B 107.9(13) . . ?
C19 C18 C17 111.70(10) . . ?
C19 C18 H18A 110.1(9) . . ?
C19 C18 H18B 110.8(10) . . ?
C18 C19 H19A 112.0(10) . . ?
C18 C19 H19B 109.3(9) . . ?
C18 C19 C20 111.11(10) . . ?
H19A C19 H19B 106.8(14) . . ?
C20 C19 H19A 108.8(10) . . ?
C20 C19 H19B 108.6(10) . . ?
C19 C20 H20A 109.3(10) . . ?
C19 C20 H20B 110.7(10) . . ?
C19 C20 C21 110.68(10) . . ?
H20A C20 H20B 105.5(13) . . ?
C21 C20 H20A 109.5(10) . . ?
C21 C20 H20B 111.0(10) . . ?
C8 C21 H21A 107.5(9) . . ?
C8 C21 H21B 110.1(9) . . ?
C20 C21 C8 112.65(9) . . ?
C20 C21 H21A 108.1(9) . . ?
C20 C21 H21B 109.8(9) . . ?
H21A C21 H21B 108.6(13) . . ?
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 C1 1.3449(14) . ?
O1 C3 1.4559(13) . ?
O2 C1 1.3602(14) . ?
O2 C2 1.4533(13) . ?
O3 C1 1.1887(14) . ?
O4 C4 1.2091(15) . ?
N1 C10 1.2990(15) . ?
N1 C11 1.4000(14) . ?
N2 C2 1.4305(14) . ?
N2 C10 1.3921(14) . ?
N2 C16 1.4134(14) . ?
C2 C3 1.5678(15) . ?
C2 C4 1.5554(15) . ?
C3 C6 1.5262(15) . ?
C3 C8 1.5514(15) . ?
C4 C5 1.4489(17) . ?
C5 H5 0.955(18) . ?
C5 C6 1.3392(17) . ?
C6 C7 1.4893(16) . ?
C7 H7A 1.01(2) . ?
C7 H7B 0.982(19) . ?
C7 H7C 0.987(19) . ?
C8 C9 1.5398(15) . ?
C8 C17 1.5464(15) . ?
C8 C21 1.5432(15) . ?
C9 H9A 0.972(15) . ?
C9 H9B 0.983(17) . ?
C9 C10 1.4829(15) . ?
C11 C12 1.3950(16) . ?
C11 C16 1.4036(15) . ?
C12 H12 0.965(17) . ?
C12 C13 1.3845(16) . ?
C13 H13 0.999(17) . ?
C13 C14 1.4023(17) . ?
C14 H14 0.991(18) . ?
C14 C15 1.3924(16) . ?
C15 H15 0.965(16) . ?
C15 C16 1.3973(15) . ?
C17 H17A 0.993(17) . ?
C17 H17B 0.994(16) . ?
C17 C18 1.5338(17) . ?
C18 H18A 1.005(16) . ?
C18 H18B 1.005(18) . ?
C18 C19 1.5282(17) . ?
C19 H19A 1.001(19) . ?
C19 H19B 1.005(17) . ?
C19 C20 1.5290(17) . ?
C20 H20A 0.999(18) . ?
C20 H20B 1.013(17) . ?
C20 C21 1.5313(16) . ?
C21 H21A 0.990(16) . ?
C21 H21B 0.980(17) . ?
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 C3 C6 C5 118.29(11) . . . . ?
O1 C3 C6 C7 -58.71(14) . . . . ?
O1 C3 C8 C9 -70.81(10) . . . . ?
O1 C3 C8 C17 47.24(11) . . . . ?
O1 C3 C8 C21 168.91(8) . . . . ?
O2 C2 C3 O1 -10.14(10) . . . . ?
O2 C2 C3 C6 102.69(9) . . . . ?
O2 C2 C3 C8 -128.16(9) . . . . ?
O2 C2 C4 O4 70.59(14) . . . . ?
O2 C2 C4 C5 -103.27(10) . . . . ?
O4 C4 C5 C6 -173.16(12) . . . . ?
N1 C11 C12 C13 -176.96(11) . . . . ?
N1 C11 C16 N2 -2.39(12) . . . . ?
N1 C11 C16 C15 175.01(10) . . . . ?
N2 C2 C3 O1 109.92(10) . . . . ?
N2 C2 C3 C6 -137.26(9) . . . . ?
N2 C2 C3 C8 -8.10(13) . . . . ?
N2 C2 C4 O4 -52.14(16) . . . . ?
N2 C2 C4 C5 134.01(10) . . . . ?
C1 O1 C3 C2 8.00(11) . . . . ?
C1 O1 C3 C6 -100.78(10) . . . . ?
C1 O1 C3 C8 132.03(9) . . . . ?
C1 O2 C2 N2 -114.35(10) . . . . ?
C1 O2 C2 C3 9.47(11) . . . . ?
C1 O2 C2 C4 119.40(9) . . . . ?
C2 O2 C1 O1 -4.98(12) . . . . ?
C2 O2 C1 O3 174.95(11) . . . . ?
C2 N2 C10 N1 179.34(9) . . . . ?
C2 N2 C10 C9 -0.11(15) . . . . ?
C2 N2 C16 C11 -179.57(11) . . . . ?
C2 N2 C16 C15 3.5(2) . . . . ?
C2 C3 C6 C5 9.69(13) . . . . ?
C2 C3 C6 C7 -167.30(11) . . . . ?
C2 C3 C8 C9 44.38(12) . . . . ?
C2 C3 C8 C17 162.43(9) . . . . ?
C2 C3 C8 C21 -75.91(11) . . . . ?
C2 C4 C5 C6 0.45(14) . . . . ?
C3 O1 C1 O2 -2.43(12) . . . . ?
C3 O1 C1 O3 177.65(11) . . . . ?
C3 C2 C4 O4 179.36(11) . . . . ?
C3 C2 C4 C5 5.51(12) . . . . ?
C3 C8 C9 C10 -59.82(11) . . . . ?
C3 C8 C17 C18 174.69(9) . . . . ?
C3 C8 C21 C20 -177.52(9) . . . . ?
C4 C2 C3 O1 -121.50(9) . . . . ?
C4 C2 C3 C6 -8.68(11) . . . . ?
C4 C2 C3 C8 120.48(10) . . . . ?
C4 C5 C6 C3 -6.65(15) . . . . ?
C4 C5 C6 C7 170.29(11) . . . . ?
C6 C3 C8 C9 166.79(9) . . . . ?
C6 C3 C8 C17 -75.16(12) . . . . ?
C6 C3 C8 C21 46.50(12) . . . . ?
C8 C3 C6 C5 -119.60(11) . . . . ?
C8 C3 C6 C7 63.41(14) . . . . ?
C8 C9 C10 N1 -138.33(11) . . . . ?
C8 C9 C10 N2 41.04(13) . . . . ?
C8 C17 C18 C19 -54.87(13) . . . . ?
C9 C8 C17 C18 -68.86(12) . . . . ?
C9 C8 C21 C20 65.81(12) . . . . ?
C10 N1 C11 C12 -179.65(11) . . . . ?
C10 N1 C11 C16 0.65(12) . . . . ?
C10 N2 C2 O2 99.63(11) . . . . ?
C10 N2 C2 C3 -16.54(14) . . . . ?
C10 N2 C2 C4 -139.45(10) . . . . ?
C10 N2 C16 C11 3.08(11) . . . . ?
C10 N2 C16 C15 -173.80(12) . . . . ?
C11 N1 C10 N2 1.48(12) . . . . ?
C11 N1 C10 C9 -179.12(10) . . . . ?
C11 C12 C13 C14 0.78(17) . . . . ?
C12 C11 C16 N2 177.89(10) . . . . ?
C12 C11 C16 C15 -4.72(17) . . . . ?
C12 C13 C14 C15 -2.48(18) . . . . ?
C13 C14 C15 C16 0.57(17) . . . . ?
C14 C15 C16 N2 179.41(11) . . . . ?
C14 C15 C16 C11 2.95(16) . . . . ?
C16 N2 C2 O2 -77.35(13) . . . . ?
C16 N2 C2 C3 166.48(10) . . . . ?
C16 N2 C2 C4 43.57(16) . . . . ?
C16 N2 C10 N1 -3.00(12) . . . . ?
C16 N2 C10 C9 177.55(9) . . . . ?
C16 C11 C12 C13 2.72(17) . . . . ?
C17 C8 C9 C10 179.86(9) . . . . ?
C17 C8 C21 C20 -54.50(13) . . . . ?
C17 C18 C19 C20 55.64(14) . . . . ?
C18 C19 C20 C21 -55.95(14) . . . . ?
C19 C20 C21 C8 56.37(13) . . . . ?
C21 C8 C9 C10 58.85(12) . . . . ?
C21 C8 C17 C18 53.33(13) . . . . ?
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
2.0015 0.9997 -0.0027 -0.1260 0.1878 0.4357
0.0009 2.0035 6.9946 -0.9995 -0.0466 0.2071
-0.0020 -2.0054 -6.9919 0.9994 0.0462 -0.2073
0.0052 -0.0023 7.9790 -0.8630 -0.3664 0.1995
0.0009 -2.9979 9.0003 -0.6106 -0.8236 0.1747
4.0024 -2.0001 2.0076 0.0146 -0.2646 0.8556
-0.0038 -5.9910 3.9864 0.2944 -1.0035 -0.0002
-0.0006 -4.0034 -4.9931 1.0251 -0.3191 -0.1901
4.9933 -2.0008 -1.9994 0.4456 -0.0557 0.9635
-4.9990 3.0030 2.0161 -0.5688 0.1920 -0.9478
4.0037 -0.0144 -3.9924 0.4232 0.2828 0.7393
-4.0034 0.0063 3.9862 -0.4216 -0.2836 -0.7395
0.0085 0.9885 -9.0021 0.8542 0.5487 -0.2058
-0.0029 6.0039 -2.0021 -0.5106 0.9141 0.0484
4.0038 0.0017 1.9737 -0.2242 0.0112 0.8879
-4.0006 -0.0053 -1.9933 0.2268 -0.0107 -0.8878
-4.0047 -1.9967 -0.0105 0.2535 -0.3745 -0.8721
