#------------------------------------------------------------------------------
#$Date: 2023-09-01 01:00:29 +0300 (Fri, 01 Sep 2023) $
#$Revision: 285933 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/20/7132082.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_7132082
loop_
_publ_author_name
'Zhang, Mengying'
'He, Yuhao'
'Li, Song'
'Geng, Yuehua'
'Liu, Xiangyang'
'Yang, Xifa'
_publ_section_title
;
 Synthesis of Spiropyrans and Arylquinones via Ru(II)-Catalyzed
 Conditions-Controlled Coupling of 3-Aryl-2H-benzoxazinones with
 Benzoquinones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC03395C
_journal_year                    2023
_chemical_formula_moiety         'C24 H21 N O4'
_chemical_formula_sum            'C24 H21 N O4'
_chemical_formula_weight         387.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc2fqvkl
_audit_creation_date             2022-07-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-04-14 deposited with the CCDC.	2023-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.869(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5790(3)
_cell_length_b                   13.6219(3)
_cell_length_c                   11.7844(2)
_cell_measurement_reflns_used    4265
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8560
_cell_measurement_theta_min      3.6210
_cell_volume                     1951.64(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_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   -105.00  -4.00   1.00    1.50    --  -33.50   0.00  30.00  101
  2  ω    -94.00 -36.00   1.00    1.50    --  -33.50 -57.00-150.00   58
  3  ω    -50.00 -24.00   1.00    1.50    --  -33.50  57.00-150.00   26
  4  ω     -1.00  25.00   1.00    1.50    --  -33.50  57.00-150.00   26
  5  ω     44.00  69.00   1.00    1.50    --   36.47 -99.00-120.00   25
  6  ω     68.00 109.00   1.00    1.50    --   36.47 178.00  30.00   41
  7  ω      3.00 106.00   1.00    1.50    --   36.47  19.00 -30.00  103
  8  ω     34.00  59.00   1.00    1.50    --   36.47 -37.00 150.00   25
  9  ω      1.00  28.00   1.00    1.50    --   36.47 -99.00-120.00   27
 10  ω    -33.00   1.00   1.00    1.50    --   36.47 -37.00 150.00   34
 11  ω     23.00  72.00   1.00    1.50    --   36.47 -99.00  30.00   49
 12  ω     -2.00  76.00   1.00    1.50    --   36.47 -99.00-180.00   78
 13  ω     58.00 103.00   1.00    1.50    --   36.47 178.00-180.00   45
 14  ω     17.00 105.00   1.00    1.50    --   36.47  77.00-180.00   88
 15  ω    147.00 175.00   1.00    7.00    --  108.00  77.00-180.00   28
 16  ω     80.00 116.00   1.00    7.00    --  108.00  77.00-180.00   36
 17  ω     72.00  98.00   1.00    7.00    --  108.00 -94.00  90.00   26
 18  ω     38.00 108.00   1.00    7.00    --  108.00 -45.00 150.00   70
 19  ω     56.00 110.00   1.00    7.00    --  108.00 -94.00-150.00   54
 20  ω    101.00 176.00   1.00    7.00    --  108.00 111.00 150.00   75
 21  ω     38.00 106.00   1.00    7.00    --  108.00 -94.00 150.00   68
 22  ω     41.00 126.00   1.00    7.00    --  108.00 -61.00-120.00   85
 23  ω    106.00 134.00   1.00    7.00    --  108.00 111.00 -60.00   28
 24  ω     93.00 127.00   1.00    7.00    --  108.00 -45.00  60.00   34
 25  ω     85.00 142.00   1.00    7.00    --  108.00  77.00  90.00   57
 26  ω     71.00 108.00   1.00    7.00    --  108.00 -94.00 -60.00   37
 27  ω     43.00 126.00   1.00    7.00    --  108.00 -30.00-150.00   83
 28  ω    115.00 175.00   1.00    7.00    --  108.00  45.00-150.00   60
 29  ω    100.00 157.00   1.00    7.00    --  108.00 111.00-120.00   57
 30  ω     65.00 138.00   1.00    7.00    --  108.00-157.00 162.00   73
 31  ω     90.00 178.00   1.00    7.00    --  108.00  45.00  30.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0065344000
_diffrn_orient_matrix_UB_12      0.1121169000
_diffrn_orient_matrix_UB_13      0.0175998000
_diffrn_orient_matrix_UB_21      -0.1171274000
_diffrn_orient_matrix_UB_22      0.0001882000
_diffrn_orient_matrix_UB_23      0.0177915000
_diffrn_orient_matrix_UB_31      0.0479685000
_diffrn_orient_matrix_UB_32      -0.0148538000
_diffrn_orient_matrix_UB_33      0.1329119000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13721
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         3.636
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3476
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0485
_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)+(0.0742P)²+0.3085P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1338
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2821
_reflns_number_total             3476
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc03395c2.cif
_cod_data_source_block           202207127
_cod_database_code               7132082
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O3N1
_chemical_oxdiff_usercomment     r
_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   0.931
_shelx_estimated_absorpt_t_min   0.911
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H4-O4
 0.9 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4A), C10(H10), C11(H11), C12(H12), C13(H13),
 C18(H18), C20(H20)
3.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_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 1.078
_oxdiff_exptl_absorpt_empirical_full_min 0.933
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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 0.92316(11) 0.71041(10) 0.81381(10) 0.0440(3) Uani 1 1 d . . . . .
O2 O 0.76561(12) 0.78053(11) 0.81115(11) 0.0521(4) Uani 1 1 d . . . . .
O3 O 0.75596(9) 0.59309(8) 0.64243(10) 0.0352(3) Uani 1 1 d . . . . .
O4 O 0.35805(13) 0.45066(13) 0.6818(2) 0.0739(6) Uani 1 1 d D . . . .
H4 H 0.360(3) 0.3892(14) 0.701(3) 0.094(11) Uiso 1 1 d D . . . .
N1 N 0.86098(12) 0.70827(11) 0.57527(12) 0.0342(3) Uani 1 1 d . . . . .
H1 H 0.8402(16) 0.7036(15) 0.499(2) 0.039(5) Uiso 1 1 d . . . . .
C1 C 1.08263(16) 0.61500(17) 0.81619(17) 0.0507(5) Uani 1 1 d . . . . .
H1A H 1.1007 0.6158 0.8978 0.061 Uiso 1 1 calc R . . . .
C2 C 1.14952(16) 0.56779(17) 0.7572(2) 0.0555(5) Uani 1 1 d . . . . .
H2 H 1.2129 0.5359 0.7990 0.067 Uiso 1 1 calc R . . . .
C3 C 1.12224(16) 0.56796(16) 0.6358(2) 0.0505(5) Uani 1 1 d . . . . .
H3 H 1.1676 0.5363 0.5963 0.061 Uiso 1 1 calc R . . . .
C4 C 1.02788(15) 0.61489(14) 0.57264(16) 0.0424(4) Uani 1 1 d . . . . .
H4A H 1.0107 0.6154 0.4910 0.051 Uiso 1 1 calc R . . . .
C5 C 0.95908(13) 0.66105(12) 0.63088(15) 0.0348(4) Uani 1 1 d . . . . .
C6 C 0.98868(14) 0.66094(13) 0.75239(15) 0.0386(4) Uani 1 1 d . . . . .
C7 C 0.81885(15) 0.73439(13) 0.75867(14) 0.0364(4) Uani 1 1 d . . . . .
C8 C 0.77446(13) 0.69702(12) 0.63176(13) 0.0321(4) Uani 1 1 d . . . . .
C9 C 0.67197(14) 0.75165(12) 0.56854(14) 0.0340(4) Uani 1 1 d . . . . .
C10 C 0.68150(17) 0.84258(14) 0.51826(17) 0.0454(4) Uani 1 1 d . . . . .
H10 H 0.7507 0.8694 0.5244 0.054 Uiso 1 1 calc R . . . .
C11 C 0.58876(19) 0.89305(16) 0.4594(2) 0.0555(5) Uani 1 1 d . . . . .
H11 H 0.5952 0.9540 0.4263 0.067 Uiso 1 1 calc R . . . .
C12 C 0.48649(18) 0.85250(16) 0.44997(19) 0.0550(5) Uani 1 1 d . . . . .
H12 H 0.4238 0.8860 0.4094 0.066 Uiso 1 1 calc R . . . .
C13 C 0.47616(16) 0.76281(15) 0.50006(17) 0.0458(4) Uani 1 1 d . . . . .
H13 H 0.4065 0.7366 0.4929 0.055 Uiso 1 1 calc R . . . .
C14 C 0.56929(14) 0.71043(13) 0.56177(14) 0.0355(4) Uani 1 1 d . . . . .
C15 C 0.56144(14) 0.61449(12) 0.61712(14) 0.0346(4) Uani 1 1 d . . . . .
C16 C 0.65684(13) 0.55913(12) 0.65795(13) 0.0319(4) Uani 1 1 d . . . . .
C17 C 0.65606(14) 0.46601(12) 0.70849(14) 0.0346(4) Uani 1 1 d . . . . .
C18 C 0.55425(15) 0.42988(13) 0.71467(16) 0.0407(4) Uani 1 1 d . . . . .
H18 H 0.5503 0.3679 0.7463 0.049 Uiso 1 1 calc R . . . .
C19 C 0.45872(15) 0.48387(15) 0.67491(18) 0.0456(4) Uani 1 1 d . . . . .
C20 C 0.46211(15) 0.57593(14) 0.62798(18) 0.0435(4) Uani 1 1 d . . . . .
H20 H 0.3979 0.6125 0.6035 0.052 Uiso 1 1 calc R . . . .
C21 C 0.76277(15) 0.40744(14) 0.75850(17) 0.0423(4) Uani 1 1 d . . . . .
C22 C 0.82269(19) 0.38654(17) 0.6625(2) 0.0566(5) Uani 1 1 d . . . . .
H22A H 0.7767 0.3469 0.6021 0.085 Uiso 1 1 calc GR . . . .
H22B H 0.8901 0.3522 0.6962 0.085 Uiso 1 1 calc GR . . . .
H22C H 0.8387 0.4474 0.6294 0.085 Uiso 1 1 calc GR . . . .
C23 C 0.83849(17) 0.46522(17) 0.85881(19) 0.0547(5) Uani 1 1 d . . . . .
H23A H 0.8565 0.5272 0.8297 0.082 Uiso 1 1 calc GR . . . .
H23B H 0.9047 0.4285 0.8899 0.082 Uiso 1 1 calc GR . . . .
H23C H 0.8017 0.4762 0.9197 0.082 Uiso 1 1 calc GR . . . .
C24 C 0.73976(19) 0.30859(16) 0.8093(2) 0.0605(6) Uani 1 1 d . . . . .
H24A H 0.7056 0.3195 0.8723 0.091 Uiso 1 1 calc GR . . . .
H24B H 0.8077 0.2738 0.8385 0.091 Uiso 1 1 calc GR . . . .
H24C H 0.6916 0.2705 0.7490 0.091 Uiso 1 1 calc GR . . . .
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_
_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
C7 O1 C6 119.79(13) . . ?
C16 O3 C8 120.60(12) . . ?
C19 O4 H4 112(2) . . ?
C5 N1 H1 116.5(14) . . ?
C5 N1 C8 114.89(13) . . ?
C8 N1 H1 114.2(13) . . ?
C2 C1 H1A 120.5 . . ?
C6 C1 H1A 120.5 . . ?
C6 C1 C2 119.03(18) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 119.92(18) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.50(19) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4A 120.0 . . ?
C3 C4 C5 120.09(17) . . ?
C5 C4 H4A 120.0 . . ?
C4 C5 N1 124.43(15) . . ?
C6 C5 N1 117.17(16) . . ?
C6 C5 C4 118.40(16) . . ?
C1 C6 O1 118.20(16) . . ?
C1 C6 C5 122.04(18) . . ?
C5 C6 O1 119.75(16) . . ?
O1 C7 C8 116.96(14) . . ?
O2 C7 O1 118.83(15) . . ?
O2 C7 C8 124.18(16) . . ?
O3 C8 C7 105.38(13) . . ?
O3 C8 C9 112.93(13) . . ?
N1 C8 O3 107.81(13) . . ?
N1 C8 C7 106.75(13) . . ?
N1 C8 C9 112.04(13) . . ?
C9 C8 C7 111.52(14) . . ?
C10 C9 C8 119.54(16) . . ?
C10 C9 C14 120.98(16) . . ?
C14 C9 C8 119.47(15) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.27(19) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.52(18) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.65(18) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 120.97(18) . . ?
C14 C13 H13 119.5 . . ?
C9 C14 C13 117.59(16) . . ?
C9 C14 C15 119.90(15) . . ?
C13 C14 C15 122.51(17) . . ?
C16 C15 C14 118.85(15) . . ?
C20 C15 C14 122.60(16) . . ?
C20 C15 C16 118.54(16) . . ?
O3 C16 C15 119.86(15) . . ?
O3 C16 C17 117.56(14) . . ?
C15 C16 C17 122.45(15) . . ?
C16 C17 C21 121.99(15) . . ?
C18 C17 C16 116.68(16) . . ?
C18 C17 C21 121.30(16) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 C17 121.69(17) . . ?
C19 C18 H18 119.2 . . ?
O4 C19 C18 122.77(18) . . ?
O4 C19 C20 116.78(17) . . ?
C20 C19 C18 120.44(17) . . ?
C15 C20 H20 119.9 . . ?
C19 C20 C15 120.16(17) . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C17 110.94(16) . . ?
C23 C21 C17 109.68(15) . . ?
C23 C21 C22 109.73(18) . . ?
C24 C21 C17 111.77(16) . . ?
C24 C21 C22 107.59(17) . . ?
C24 C21 C23 107.03(17) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
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 C6 1.401(2) . ?
O1 C7 1.346(2) . ?
O2 C7 1.200(2) . ?
O3 C8 1.445(2) . ?
O3 C16 1.385(2) . ?
O4 H4 0.868(18) . ?
O4 C19 1.367(2) . ?
N1 H1 0.87(2) . ?
N1 C5 1.397(2) . ?
N1 C8 1.422(2) . ?
C1 H1A 0.9300 . ?
C1 C2 1.380(3) . ?
C1 C6 1.377(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(3) . ?
C4 H4A 0.9300 . ?
C4 C5 1.386(3) . ?
C5 C6 1.384(2) . ?
C7 C8 1.542(2) . ?
C8 C9 1.509(2) . ?
C9 C10 1.391(3) . ?
C9 C14 1.392(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.378(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.378(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.377(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.405(2) . ?
C14 C15 1.475(2) . ?
C15 C16 1.394(2) . ?
C15 C20 1.391(3) . ?
C16 C17 1.402(2) . ?
C17 C18 1.391(2) . ?
C17 C21 1.543(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.384(3) . ?
C19 C20 1.376(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.538(3) . ?
C21 C23 1.532(3) . ?
C21 C24 1.531(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
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
O4 H4 O2 0.868(18) 2.14(3) 2.804(2) 133(3) 2_646
N1 H1 O1 0.87(2) 2.90(2) 3.5454(18) 132.5(16) 4_575
N1 H1 O2 0.87(2) 2.18(2) 3.0387(19) 167.5(19) 4_575
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 C7 C8 O3 73.71(18) . . . . ?
O1 C7 C8 N1 -40.75(19) . . . . ?
O1 C7 C8 C9 -163.42(15) . . . . ?
O2 C7 C8 O3 -104.21(19) . . . . ?
O2 C7 C8 N1 141.34(18) . . . . ?
O2 C7 C8 C9 18.7(2) . . . . ?
O3 C8 C9 C10 -159.44(15) . . . . ?
O3 C8 C9 C14 20.8(2) . . . . ?
O3 C16 C17 C18 -174.98(14) . . . . ?
O3 C16 C17 C21 6.9(2) . . . . ?
O4 C19 C20 C15 -179.46(19) . . . . ?
N1 C5 C6 O1 -2.6(2) . . . . ?
N1 C5 C6 C1 178.78(17) . . . . ?
N1 C8 C9 C10 -37.5(2) . . . . ?
N1 C8 C9 C14 142.75(16) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C1 C6 O1 -178.55(18) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 N1 -178.43(17) . . . . ?
C3 C4 C5 C6 1.6(3) . . . . ?
C4 C5 C6 O1 177.41(16) . . . . ?
C4 C5 C6 C1 -1.3(3) . . . . ?
C5 N1 C8 O3 -56.40(17) . . . . ?
C5 N1 C8 C7 56.40(18) . . . . ?
C5 N1 C8 C9 178.74(14) . . . . ?
C6 O1 C7 O2 -176.73(17) . . . . ?
C6 O1 C7 C8 5.2(2) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C7 O1 C6 C1 -163.19(17) . . . . ?
C7 O1 C6 C5 18.1(2) . . . . ?
C7 C8 C9 C10 82.12(19) . . . . ?
C7 C8 C9 C14 -97.66(18) . . . . ?
C8 O3 C16 C15 26.2(2) . . . . ?
C8 O3 C16 C17 -157.73(14) . . . . ?
C8 N1 C5 C4 142.69(17) . . . . ?
C8 N1 C5 C6 -37.3(2) . . . . ?
C8 C9 C10 C11 179.47(17) . . . . ?
C8 C9 C14 C13 -178.72(15) . . . . ?
C8 C9 C14 C15 0.5(2) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C9 C14 C15 C16 -10.8(2) . . . . ?
C9 C14 C15 C20 170.66(17) . . . . ?
C10 C9 C14 C13 1.5(3) . . . . ?
C10 C9 C14 C15 -179.23(16) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C9 -1.1(3) . . . . ?
C12 C13 C14 C15 179.65(18) . . . . ?
C13 C14 C15 C16 168.46(16) . . . . ?
C13 C14 C15 C20 -10.1(3) . . . . ?
C14 C9 C10 C11 -0.7(3) . . . . ?
C14 C15 C16 O3 -2.2(2) . . . . ?
C14 C15 C16 C17 -178.09(15) . . . . ?
C14 C15 C20 C19 176.65(17) . . . . ?
C15 C16 C17 C18 1.0(2) . . . . ?
C15 C16 C17 C21 -177.15(15) . . . . ?
C16 O3 C8 N1 -158.95(13) . . . . ?
C16 O3 C8 C7 87.33(16) . . . . ?
C16 O3 C8 C9 -34.63(19) . . . . ?
C16 C15 C20 C19 -1.9(3) . . . . ?
C16 C17 C18 C19 -1.1(3) . . . . ?
C16 C17 C21 C22 -60.3(2) . . . . ?
C16 C17 C21 C23 61.1(2) . . . . ?
C16 C17 C21 C24 179.61(17) . . . . ?
C17 C18 C19 O4 -178.9(2) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
C18 C17 C21 C22 121.65(19) . . . . ?
C18 C17 C21 C23 -116.97(19) . . . . ?
C18 C17 C21 C24 1.6(3) . . . . ?
C18 C19 C20 C15 1.8(3) . . . . ?
C20 C15 C16 O3 176.39(15) . . . . ?
C20 C15 C16 C17 0.5(3) . . . . ?
C21 C17 C18 C19 176.99(17) . . . . ?
