#------------------------------------------------------------------------------
#$Date: 2024-05-05 05:48:18 +0200 (Sun 05 de May de 2024) $
#$Revision: 291672 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/30/7063084.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_7063084
loop_
_publ_author_name
'Das, Arindam'
'Dey, Sovan'
'Yadav, Ram Naresh'
'Dutta, Prajna'
'Dhiman, Shubham'
'Boruah, Palash Jyoti'
'Sarkar, Koushik'
'Sahu, Abhishek'
'Jana, Anupam'
'Paul, Amit Kumar'
'Hossain, Md. Firoj'
_publ_section_title
;
 Unleashing naphthopyranopyrimidine's anticancer potential: a deep
 eutectic solvent (DES) study
;
_journal_issue                   17
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7566
_journal_page_last               7578
_journal_paper_doi               10.1039/D4NJ00796D
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C23 H17 N3 O5'
_chemical_formula_sum            'C23 H17 N3 O5'
_chemical_formula_weight         415.39
_chemical_name_systematic
8,10-dimethyl-12-(4-nitrophenyl)-7a,8,11a,12-tetrahydro-9H-benzo[5,6]chromeno[2,3-d]pyrimidine-9,11(10H)-dione
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-04-12
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-08-08 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.31509(6)
_cell_length_b                   19.69557(13)
_cell_length_c                   20.17380(14)
_cell_measurement_reflns_used    32945
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      68.0230
_cell_measurement_theta_min      2.1730
_cell_volume                     3701.21(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     44.00 127.00   0.50    0.20    --   96.67-145.00-120.00  166
  2  ω     41.00 100.00   0.50    0.20    --   41.08-138.00-150.00  118
  3  ω    -83.00 -14.00   0.50    0.20    --  -82.50  68.00-140.00  138
  4  ω    -65.00  27.00   0.50    0.20    --  -41.08  68.00-140.00  184
  5  ω    -68.00  28.00   0.50    0.20    --  -41.08  77.00 -22.00  192
  6  ω   -105.00 -14.00   0.50    0.20    --  -82.50  77.00  92.00  182
  7  ω    -47.00 -15.00   0.50    0.20    --  -82.50  42.00  90.00   64
  8  ω     14.00 110.00   0.50    0.20    --   41.08  77.00  92.00  192
  9  ω     70.00 165.00   0.50    0.20    --   96.67  77.00  92.00  190
 10  ω     70.00 165.00   0.50    0.20    --   96.67  77.00 120.00  190
 11  ω     70.00 165.00   0.50    0.20    --   96.67  77.00 -22.00  190
 12  ω     14.00 110.00   0.50    0.20    --   41.08  77.00 -90.00  192
 13  ω     17.00 109.00   0.50    0.20    --   41.08  68.00-140.00  184
 14  ω     73.00 165.00   0.50    0.20    --   96.67  68.00-180.00  184
 15  ω     73.00 165.00   0.50    0.20    --   96.67  68.00-140.00  184
 16  ω     82.00 167.00   0.50    0.20    --   96.67  25.00  30.00  170
 17  ω     82.00 167.00   0.50    0.20    --   96.67  25.00 -60.00  170
 18  ω     75.00 164.00   0.50    0.20    --   96.67  59.00  30.00  178
 19  ω     75.00 164.00   0.50    0.20    --   96.67  59.00  60.00  178
 20  ω     75.00 164.00   0.50    0.20    --   96.67  59.00 150.00  178
 21  ω     30.00  57.00   0.50    0.20    --   96.67 -50.00 120.00   54
 22  ω     29.00  83.00   0.50    0.20    --   96.67 -68.00  85.00  108
 23  ω     29.00  68.00   0.50    0.20    --   96.67 -59.00 120.00   78
 24  ω     29.00  68.00   0.50    0.20    --   96.67 -59.00  30.00   78
 25  ω     29.00  68.00   0.50    0.20    --   96.67 -59.00   0.00   78
 26  ω     28.00 105.00   0.50    0.20    --   96.67 -77.00 -33.00  154
 27  ω     28.00 105.00   0.50    0.20    --   96.67 -77.00-147.00  154
 28  ω     29.00  68.00   0.50    0.20    --   96.67 -59.00-150.00   78
 29  ω     29.00  68.00   0.50    0.20    --   96.67 -59.00-120.00   78
 30  ω     30.00  57.00   0.50    0.20    --   96.67 -50.00-120.00   54
 31  ω     30.00  57.00   0.50    0.20    --   96.67 -50.00 -90.00   54
 32  ω     30.00  57.00   0.50    0.20    --   96.67 -50.00  90.00   54
 33  ω    -27.00  68.00   0.50    0.20    --   41.08 -77.00 -33.00  190
 34  ω    -27.00  65.00   0.50    0.20    --   41.08 -68.00  85.00  184
 35  ω    -29.00  31.00   0.50    0.20    --   41.08 -25.00 120.00  120
 36  ω    -27.00  68.00   0.50    0.20    --   41.08 -77.00-147.00  190
 37  ω    -34.00  24.00   0.50    0.20    --   41.08 -12.00-180.00  116
 38  ω   -110.00 -14.00   0.50    0.20    --  -41.08 -77.00-120.00  192
 39  ω   -108.00 -18.00   0.50    0.20    --  -41.08 -64.00 -90.00  180
 40  ω   -110.00 -14.00   0.50    0.20    --  -41.08 -77.00   0.00  192
 41  ω   -109.00 -17.00   0.50    0.20    --  -41.08 -68.00  85.00  184
 42  ω   -108.00 -18.00   0.50    0.20    --  -41.08 -64.00 150.00  180
 43  ω   -110.00 -14.00   0.50    0.20    --  -41.08 -77.00 120.00  192
 44  ω   -108.00 -22.00   0.50    0.20    --  -41.08 -50.00   0.00  172
 45  ω   -107.00 -26.00   0.50    0.20    --  -41.08 -38.00-180.00  162
 46  ω   -151.00 -55.00   0.50    0.20    --  -82.50 -77.00-147.00  192
 47  ω   -151.00 -55.00   0.50    0.20    --  -82.50 -77.00 -33.00  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0118889000
_diffrn_orient_matrix_UB_12      -0.0570682000
_diffrn_orient_matrix_UB_13      0.0519260000
_diffrn_orient_matrix_UB_21      0.1383998000
_diffrn_orient_matrix_UB_22      -0.0324671000
_diffrn_orient_matrix_UB_23      -0.0272352000
_diffrn_orient_matrix_UB_31      0.0896869000
_diffrn_orient_matrix_UB_32      0.0425318000
_diffrn_orient_matrix_UB_33      0.0489333000
_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  0.0982
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            44160
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.186
_diffrn_reflns_theta_min         4.383
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.890
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_description       needle
_exptl_crystal_F_000             1728
_exptl_crystal_preparation       'Crystal was prepared from ethylacetate'
_exptl_crystal_recrystallization_method
'crystal was prepared from ethyl acetate solvent'
_exptl_crystal_size_max          0.002
_exptl_crystal_size_mid          0.002
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.00147(13)
_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   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3378
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0516P)²+1.7747P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.0982
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3241
_reflns_number_total             3378
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj00796d2.cif
_cod_data_source_block           kskkc054_auto
_cod_depositor_comments          'Adding full bibliography for 7063084.cif.'
_cod_database_code               7063084
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     100K
_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   0.999
_shelx_estimated_absorpt_t_min   0.998
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H31A,H31B,H31C} of C31
 At 1.5 times of:
  {H30A,H30B,H30C} of C30
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C17(H17), C3(H3), C24(H24), C18(H18), C23(H23), C21(H21), C16(H16),
 C20(H20), C2(H2)
2.c Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C30(H30A,H30B,H30C)
;
_olex2_exptl_crystal_mounting_method 'crystal mounted fron rigako instrument'
_olex2_submission_original_sample_id SD10054
_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 1.742
_oxdiff_exptl_absorpt_empirical_full_min 0.543
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
O5 O 0.10782(10) 0.00460(4) 0.85492(5) 0.0180(2) Uani 1 1 d . . . . .
O29 O -0.31370(11) -0.05321(5) 0.95178(5) 0.0251(2) Uani 1 1 d . . . . .
O28 O -0.11919(10) 0.15202(5) 1.00714(5) 0.0203(2) Uani 1 1 d . . . . .
O27 O -0.12842(12) 0.40450(5) 0.77529(5) 0.0287(3) Uani 1 1 d . . . . .
N9 N -0.21666(12) 0.04938(5) 0.98022(5) 0.0175(3) Uani 1 1 d . . . . .
N25 N -0.13324(12) 0.34530(6) 0.75629(6) 0.0197(3) Uani 1 1 d . . . . .
O26 O -0.19433(13) 0.32747(5) 0.70542(5) 0.0334(3) Uani 1 1 d . . . . .
N7 N -0.10036(12) -0.02327(5) 0.90481(5) 0.0174(3) Uani 1 1 d . . . . .
C10 C -0.10971(14) 0.09939(6) 0.97519(6) 0.0165(3) Uani 1 1 d . . . . .
C15 C 0.41341(14) 0.19884(6) 0.91537(6) 0.0161(3) Uani 1 1 d . . . . .
H15 H 0.337278 0.221799 0.937262 0.019 Uiso 1 1 calc R U . . .
C8 C -0.21778(14) -0.01162(7) 0.94610(6) 0.0185(3) Uani 1 1 d . . . . .
C14 C 0.38716(13) 0.13541(6) 0.88433(6) 0.0149(3) Uani 1 1 d . . . . .
C12 C 0.12153(13) 0.13720(6) 0.91810(6) 0.0142(3) Uani 1 1 d . . . . .
H12 H 0.152745 0.156648 0.961560 0.017 Uiso 1 1 calc R U . . .
C17 C 0.66272(14) 0.19493(7) 0.88188(7) 0.0192(3) Uani 1 1 d . . . . .
H17 H 0.755340 0.215120 0.881685 0.023 Uiso 1 1 calc R U . . .
C6 C 0.00558(14) 0.02464(6) 0.89796(6) 0.0159(3) Uani 1 1 d . . . . .
C3 C 0.34795(15) 0.00975(7) 0.81964(6) 0.0185(3) Uani 1 1 d . . . . .
H3 H 0.332350 -0.032337 0.797796 0.022 Uiso 1 1 calc R U . . .
C13 C 0.24938(14) 0.10361(6) 0.88522(6) 0.0151(3) Uani 1 1 d . . . . .
C4 C 0.23579(14) 0.04201(6) 0.85393(6) 0.0157(3) Uani 1 1 d . . . . .
C22 C -0.06252(14) 0.29362(6) 0.79715(7) 0.0164(3) Uani 1 1 d . . . . .
C19 C 0.06119(13) 0.19452(6) 0.87496(6) 0.0143(3) Uani 1 1 d . . . . .
C24 C 0.04312(13) 0.26017(6) 0.89952(6) 0.0168(3) Uani 1 1 d . . . . .
H24 H 0.073468 0.270589 0.943316 0.020 Uiso 1 1 calc R U . . .
C11 C 0.00679(13) 0.08434(6) 0.93062(6) 0.0155(3) Uani 1 1 d . . . . .
C18 C 0.64035(14) 0.13387(7) 0.85071(7) 0.0182(3) Uani 1 1 d . . . . .
H18 H 0.717960 0.112126 0.828743 0.022 Uiso 1 1 calc R U . . .
C23 C -0.01881(14) 0.31048(6) 0.86062(7) 0.0177(3) Uani 1 1 d . . . . .
H23 H -0.030836 0.355287 0.877161 0.021 Uiso 1 1 calc R U . . .
C21 C -0.04447(14) 0.22919(7) 0.77069(6) 0.0183(3) Uani 1 1 d . . . . .
H21 H -0.074628 0.219099 0.726796 0.022 Uiso 1 1 calc R U . . .
C1 C 0.50342(14) 0.10289(6) 0.85086(6) 0.0162(3) Uani 1 1 d . . . . .
C16 C 0.54804(14) 0.22735(7) 0.91404(6) 0.0178(3) Uani 1 1 d . . . . .
H16 H 0.563755 0.269764 0.935269 0.021 Uiso 1 1 calc R U . . .
C20 C 0.01864(14) 0.18011(6) 0.81000(6) 0.0173(3) Uani 1 1 d . . . . .
H20 H 0.033370 0.135832 0.792608 0.021 Uiso 1 1 calc R U . . .
C2 C 0.47946(14) 0.03994(7) 0.81828(6) 0.0180(3) Uani 1 1 d . . . . .
H2 H 0.556175 0.018631 0.795260 0.022 Uiso 1 1 calc R U . . .
C31 C -0.09030(15) -0.08832(7) 0.86922(7) 0.0214(3) Uani 1 1 d . . . . .
H31A H -0.091387 -0.079925 0.821340 0.026 Uiso 1 1 calc R U . . .
H31B H -0.172076 -0.117098 0.881236 0.026 Uiso 1 1 calc R U . . .
H31C H -0.000722 -0.111249 0.881381 0.026 Uiso 1 1 calc R U . . .
C30 C -0.34234(15) 0.06517(7) 1.02170(7) 0.0217(3) Uani 1 1 d . . . . .
H30A H -0.311104 0.089553 1.061515 0.033 Uiso 1 1 calc R U . . .
H30B H -0.390178 0.022880 1.034633 0.033 Uiso 1 1 calc R U . . .
H30C H -0.409381 0.093587 0.996568 0.033 Uiso 1 1 calc R U . . .
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
C6 O5 C4 117.14(10) . . ?
C10 N9 C30 117.19(11) . . ?
C8 N9 C10 125.30(11) . . ?
C8 N9 C30 117.38(11) . . ?
O27 N25 C22 117.85(11) . . ?
O26 N25 O27 123.41(11) . . ?
O26 N25 C22 118.74(11) . . ?
C8 N7 C31 119.00(11) . . ?
C6 N7 C8 120.76(11) . . ?
C6 N7 C31 120.24(11) . . ?
O28 C10 N9 120.31(12) . . ?
O28 C10 C11 123.89(12) . . ?
N9 C10 C11 115.80(11) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C16 C15 C14 120.57(12) . . ?
O29 C8 N9 122.85(12) . . ?
O29 C8 N7 121.43(12) . . ?
N9 C8 N7 115.72(11) . . ?
C15 C14 C13 122.38(11) . . ?
C15 C14 C1 118.23(12) . . ?
C1 C14 C13 119.39(11) . . ?
C13 C12 H12 108.8 . . ?
C13 C12 C19 111.18(10) . . ?
C19 C12 H12 108.8 . . ?
C11 C12 H12 108.8 . . ?
C11 C12 C13 109.13(10) . . ?
C11 C12 C19 110.04(10) . . ?
C18 C17 H17 120.2 . . ?
C18 C17 C16 119.65(12) . . ?
C16 C17 H17 120.2 . . ?
O5 C6 N7 111.81(11) . . ?
O5 C6 C11 124.37(12) . . ?
C11 C6 N7 123.81(12) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.78(12) . . ?
C14 C13 C12 121.35(11) . . ?
C4 C13 C14 117.68(12) . . ?
C4 C13 C12 120.96(11) . . ?
O5 C4 C3 113.69(11) . . ?
C13 C4 O5 122.43(11) . . ?
C13 C4 C3 123.86(12) . . ?
C23 C22 N25 119.06(11) . . ?
C23 C22 C21 122.68(12) . . ?
C21 C22 N25 118.25(11) . . ?
C24 C19 C12 121.69(11) . . ?
C24 C19 C20 119.14(11) . . ?
C20 C19 C12 119.13(11) . . ?
C19 C24 H24 119.7 . . ?
C23 C24 C19 120.70(12) . . ?
C23 C24 H24 119.7 . . ?
C10 C11 C12 119.66(11) . . ?
C6 C11 C10 118.59(12) . . ?
C6 C11 C12 121.63(12) . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C1 120.93(12) . . ?
C1 C18 H18 119.5 . . ?
C22 C23 C24 118.26(12) . . ?
C22 C23 H23 120.9 . . ?
C24 C23 H23 120.9 . . ?
C22 C21 H21 121.0 . . ?
C20 C21 C22 118.09(12) . . ?
C20 C21 H21 121.0 . . ?
C18 C1 C14 119.44(12) . . ?
C18 C1 C2 121.15(12) . . ?
C2 C1 C14 119.41(12) . . ?
C15 C16 C17 121.17(12) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C19 C20 H20 119.4 . . ?
C21 C20 C19 121.11(12) . . ?
C21 C20 H20 119.4 . . ?
C3 C2 C1 120.86(12) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
N7 C31 H31A 109.5 . . ?
N7 C31 H31B 109.5 . . ?
N7 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N9 C30 H30A 109.5 . . ?
N9 C30 H30B 109.5 . . ?
N9 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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
O5 C6 1.3478(16) . ?
O5 C4 1.4015(15) . ?
O29 C8 1.2175(16) . ?
O28 C10 1.2239(16) . ?
O27 N25 1.2282(15) . ?
N9 C10 1.4047(17) . ?
N9 C8 1.3847(17) . ?
N9 C30 1.4723(17) . ?
N25 O26 1.2247(16) . ?
N25 C22 1.4661(16) . ?
N7 C8 1.3938(17) . ?
N7 C6 1.3724(17) . ?
N7 C31 1.4717(17) . ?
C10 C11 1.4400(18) . ?
C15 H15 0.9500 . ?
C15 C14 1.4187(18) . ?
C15 C16 1.3744(18) . ?
C14 C13 1.4282(18) . ?
C14 C1 1.4280(18) . ?
C12 H12 1.0000 . ?
C12 C13 1.5153(17) . ?
C12 C19 1.5322(17) . ?
C12 C11 1.5134(17) . ?
C17 H17 0.9500 . ?
C17 C18 1.3730(19) . ?
C17 C16 1.4036(19) . ?
C6 C11 1.3478(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.4049(19) . ?
C3 C2 1.3620(19) . ?
C13 C4 1.3735(18) . ?
C22 C23 1.3841(19) . ?
C22 C21 1.3869(18) . ?
C19 C24 1.3950(18) . ?
C19 C20 1.3980(18) . ?
C24 H24 0.9500 . ?
C24 C23 1.3895(19) . ?
C18 H18 0.9500 . ?
C18 C1 1.4139(18) . ?
C23 H23 0.9500 . ?
C21 H21 0.9500 . ?
C21 C20 1.3818(19) . ?
C1 C2 1.4208(18) . ?
C16 H16 0.9500 . ?
C20 H20 0.9500 . ?
C2 H2 0.9500 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
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
O5 C6 C11 C10 179.89(11) . . . . ?
O5 C6 C11 C12 4.01(19) . . . . ?
O28 C10 C11 C12 -3.93(19) . . . . ?
O28 C10 C11 C6 -179.89(12) . . . . ?
O27 N25 C22 C23 12.61(18) . . . . ?
O27 N25 C22 C21 -168.49(12) . . . . ?
N9 C10 C11 C12 175.60(10) . . . . ?
N9 C10 C11 C6 -0.37(17) . . . . ?
N25 C22 C23 C24 177.61(11) . . . . ?
N25 C22 C21 C20 -178.24(11) . . . . ?
O26 N25 C22 C23 -167.07(12) . . . . ?
O26 N25 C22 C21 11.83(18) . . . . ?
N7 C6 C11 C10 -0.33(19) . . . . ?
N7 C6 C11 C12 -176.21(11) . . . . ?
C10 N9 C8 O29 -179.42(12) . . . . ?
C10 N9 C8 N7 1.27(18) . . . . ?
C15 C14 C13 C12 1.72(18) . . . . ?
C15 C14 C13 C4 -179.66(11) . . . . ?
C15 C14 C1 C18 1.19(18) . . . . ?
C15 C14 C1 C2 -178.83(11) . . . . ?
C8 N9 C10 O28 179.40(12) . . . . ?
C8 N9 C10 C11 -0.14(18) . . . . ?
C8 N7 C6 O5 -178.64(11) . . . . ?
C8 N7 C6 C11 1.55(19) . . . . ?
C14 C15 C16 C17 0.29(19) . . . . ?
C14 C13 C4 O5 176.35(11) . . . . ?
C14 C13 C4 C3 -1.99(18) . . . . ?
C14 C1 C2 C3 -1.20(19) . . . . ?
C12 C13 C4 O5 -5.03(18) . . . . ?
C12 C13 C4 C3 176.63(12) . . . . ?
C12 C19 C24 C23 -176.58(11) . . . . ?
C12 C19 C20 C21 175.99(11) . . . . ?
C17 C18 C1 C14 -0.46(19) . . . . ?
C17 C18 C1 C2 179.56(12) . . . . ?
C6 O5 C4 C3 166.34(11) . . . . ?
C6 O5 C4 C13 -12.16(17) . . . . ?
C6 N7 C8 O29 178.76(12) . . . . ?
C6 N7 C8 N9 -1.92(17) . . . . ?
C13 C14 C1 C18 -179.14(11) . . . . ?
C13 C14 C1 C2 0.84(18) . . . . ?
C13 C12 C19 C24 -125.91(12) . . . . ?
C13 C12 C19 C20 56.29(15) . . . . ?
C13 C12 C11 C10 165.07(11) . . . . ?
C13 C12 C11 C6 -19.09(16) . . . . ?
C4 O5 C6 N7 -167.01(10) . . . . ?
C4 O5 C6 C11 12.80(17) . . . . ?
C4 C3 C2 C1 0.00(19) . . . . ?
C22 C21 C20 C19 0.97(19) . . . . ?
C19 C12 C13 C14 76.30(14) . . . . ?
C19 C12 C13 C4 -102.28(13) . . . . ?
C19 C12 C11 C10 -72.68(14) . . . . ?
C19 C12 C11 C6 103.16(14) . . . . ?
C19 C24 C23 C22 0.30(19) . . . . ?
C24 C19 C20 C21 -1.87(19) . . . . ?
C11 C12 C13 C14 -162.14(11) . . . . ?
C11 C12 C13 C4 19.28(15) . . . . ?
C11 C12 C19 C24 113.06(13) . . . . ?
C11 C12 C19 C20 -64.74(14) . . . . ?
C18 C17 C16 C15 0.5(2) . . . . ?
C18 C1 C2 C3 178.78(12) . . . . ?
C23 C22 C21 C20 0.6(2) . . . . ?
C21 C22 C23 C24 -1.2(2) . . . . ?
C1 C14 C13 C12 -177.93(11) . . . . ?
C1 C14 C13 C4 0.69(18) . . . . ?
C16 C15 C14 C13 179.23(12) . . . . ?
C16 C15 C14 C1 -1.11(18) . . . . ?
C16 C17 C18 C1 -0.38(19) . . . . ?
C20 C19 C24 C23 1.22(19) . . . . ?
C2 C3 C4 O5 -176.79(11) . . . . ?
C2 C3 C4 C13 1.7(2) . . . . ?
C31 N7 C8 O29 -2.13(19) . . . . ?
C31 N7 C8 N9 177.19(11) . . . . ?
C31 N7 C6 O5 2.26(16) . . . . ?
C31 N7 C6 C11 -177.55(12) . . . . ?
C30 N9 C10 O28 3.74(17) . . . . ?
C30 N9 C10 C11 -175.80(11) . . . . ?
C30 N9 C8 O29 -3.77(19) . . . . ?
C30 N9 C8 N7 176.92(11) . . . . ?
