#------------------------------------------------------------------------------
#$Date: 2024-07-05 21:01:12 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293280 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/99/7159921.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_7159921
loop_
_publ_author_name
'Kumar Yadav, Anup'
'Yadav, Dhananjay'
'Kumar, Vipin'
'Ray, Subhasish'
'Singh, Maya Shankar'
_publ_section_title
;
 PIDA-promoted metal-free [3 + 2] heteroannulation of
 β-ketothioamides with 4-hydroxy coumarins: chemo-/regioselective
 access to furo[3,2-c]chromen-4-ones at room temperature.
;
_journal_issue                   21
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4326
_journal_page_last               4331
_journal_paper_doi               10.1039/d4ob00438h
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C24 H15 N O4'
_chemical_formula_sum            'C24 H15 N O4'
_chemical_formula_weight         381.37
_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     dual
_audit_creation_date             2023-09-30
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-10-02 deposited with the CCDC.	2024-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.4669(3)
_cell_length_b                   8.12770(10)
_cell_length_c                   21.7889(4)
_cell_measurement_reflns_used    9902
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.6510
_cell_measurement_theta_min      4.0460
_cell_volume                     3624.56(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_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    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00   0.00   0.50    1.74    --  -40.83 104.00 -67.00  146
  2  ω    -80.00 -55.00   0.50    1.74    --  -40.83 136.00   3.00   50
  3  ω    -27.00  23.00   0.50    1.74    --  -40.83  20.00 142.00  100
  4  ω   -113.00 -30.00   0.50    1.74    --  -40.83 -20.00 -23.00  166
  5  ω      1.00  26.00   0.50    1.74    --   40.83 -20.00 -23.00   50
  6  ω     41.00  67.00   0.50    1.74    --   40.83-104.00-168.00   52
  7  ω     57.00 102.00   0.50    1.74    --   40.83  20.00 142.00   90
  8  ω     46.00  95.00   0.50    1.74    --   40.83-133.00 117.00   98
  9  ω    -65.00 -30.00   0.50    1.74    --  -82.50 104.00 -67.00   70
 10  ω   -122.00 -96.00   0.50    1.74    --  -82.50 -20.00 -23.00   52
 11  ω   -148.00 -70.00   0.50    1.74    --  -82.50-136.00 -60.00  156
 12  ω   -130.00-104.00   0.50    1.74    --  -82.50-104.00-168.00   52
 13  ω     88.00 116.00   0.50    1.74    --  104.00-136.00 -60.00   56
 14  ω    106.00 131.00   0.50    1.74    --  104.00  20.00 142.00   50
 15  ω    105.00 130.00   0.50    1.74    --  104.00 133.00-174.00   50
 16  ω     46.00  71.00   0.50    1.74    --  104.00-104.00-168.00   50
 17  ω     78.00 103.00   0.50    1.74    --  104.00-133.00 117.00   50
 18  ω    120.00 145.00   0.50    1.74    --  104.00 136.00   3.00   50
 19  ω    116.00 142.00   0.50    1.74    --  104.00 104.00 -67.00   52
 20  ω   -107.00 -14.00   0.50    1.74    --  -40.83 -77.00 -60.00  186
 21  ω     -6.00  19.00   0.50    1.74    --  -40.83  32.00 -60.00   50
 22  ω     -5.00  20.00   0.50    1.74    --   40.83 -11.00 120.00   50
 23  ω    -46.00 -15.00   0.50    1.74    --  -82.50  42.00 -90.00   62
 24  ω    -57.00 -21.00   0.50    1.74    --  -82.50  50.00-180.00   72
 25  ω     38.00  68.00   0.50    1.74    --  104.00 -59.00   0.00   60
 26  ω     36.00  65.00   0.50    1.74    --  104.00 -59.00 -60.00   58
 27  ω     36.00  64.00   0.50    1.74    --  104.00 -59.00-120.00   56
 28  ω     53.00  79.00   0.50    1.74    --  104.00-111.00 150.00   52
 29  ω     36.00  83.00   0.50    1.74    --  104.00 -68.00-180.00   94
 30  ω     52.00 103.00   0.50    1.74    --  104.00-111.00 -30.00  102
 31  ω     46.00  71.00   0.50    1.74    --  104.00 -93.00 120.00   50
 32  ω     36.00  61.00   0.50    1.74    --  104.00 -68.00 -90.00   50
 33  ω     90.00 115.00   0.50    1.74    --  104.00  33.00-180.00   50
 34  ω     36.00  67.00   0.50    1.74    --  104.00 -59.00  90.00   62
 35  ω     88.00 117.00   0.50    1.74    --  104.00-133.00 -90.00   58
 36  ω     53.00  78.00   0.50    1.74    --  104.00-133.00 -90.00   50
 37  ω    105.00 161.00   0.50    1.74    --  104.00  93.00 -90.00  112
 38  ω     38.00  66.00   0.50    1.74    --  104.00-133.00  90.00   56
 39  ω     79.00 105.00   0.50    1.74    --  104.00-133.00  90.00   52
 40  ω     60.00 108.00   0.50    1.74    --  104.00-111.00 120.00   96
 41  ω     37.00  77.00   0.50    1.74    --  104.00 -68.00 150.00   80
 42  ω     53.00  79.00   0.50    1.74    --  104.00 -68.00-150.00   52
 43  ω     48.00  73.00   0.50    1.74    --  104.00 -93.00-120.00   50
 44  ω    125.00 172.00   0.50    1.74    --  104.00  33.00-180.00   94
 45  ω     80.00 105.00   0.50    1.74    --  104.00 -93.00 120.00   50
 46  ω     79.00 141.00   0.50    1.74    --  104.00  17.00  30.00  124
 47  ω     89.00 138.00   0.50    1.74    --  104.00 133.00-180.00   98
;
_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      -0.0344018000
_diffrn_orient_matrix_UB_12      -0.0255982000
_diffrn_orient_matrix_UB_13      -0.0621407000
_diffrn_orient_matrix_UB_21      -0.0638851000
_diffrn_orient_matrix_UB_22      -0.0436300000
_diffrn_orient_matrix_UB_23      0.0337126000
_diffrn_orient_matrix_UB_31      -0.0200693000
_diffrn_orient_matrix_UB_32      0.1826497000
_diffrn_orient_matrix_UB_33      -0.0006740000
_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  0.0311
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21846
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.047
_diffrn_reflns_theta_min         4.058
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.785
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       plate
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3536
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0413
_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)+(0.0662P)²+0.2566P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1190
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2701
_reflns_number_total             3536
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00438h2.cif
_cod_data_source_block           aky-45_autored
_cod_depositor_comments
'Adding full bibliography for 7159921--7159922.cif.'
_cod_database_code               7159921
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O S'
_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   0.962
_shelx_estimated_absorpt_t_min   0.859
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C20(H20), C24(H24), C3(H3), C13(H13), C7(H7), C15(H15), C2(H2),
 C17(H17), C9(H9), C19(H19), C5(H5), C21(H21), C11(H11), C23(H23)
;
_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 1.221
_oxdiff_exptl_absorpt_empirical_full_min 0.794
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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 0.67367(5) 0.81836(13) 0.58528(5) 0.0574(3) Uani 1 1 d . . . . .
O4 O 0.84633(5) 0.67013(13) 0.51239(5) 0.0639(3) Uani 1 1 d . . . . .
O2 O 0.79399(5) 0.52242(15) 0.44301(6) 0.0713(3) Uani 1 1 d . . . . .
O3 O 0.56187(6) 0.56363(18) 0.46090(6) 0.0831(4) Uani 1 1 d . . . . .
N1 N 0.56621(6) 0.76587(18) 0.55787(6) 0.0649(4) Uani 1 1 d . . . . .
H1 H 0.540478 0.707252 0.535604 0.078 Uiso 1 1 calc R U . . .
C1 C 0.73426(7) 0.77496(18) 0.56300(7) 0.0531(3) Uani 1 1 d . . . . .
C4 C 0.64803(7) 0.53113(17) 0.39200(7) 0.0547(4) Uani 1 1 d . . . . .
C6 C 0.72914(7) 0.68197(16) 0.51167(7) 0.0514(3) Uani 1 1 d . . . . .
C8 C 0.79273(7) 0.82289(18) 0.59287(7) 0.0549(4) Uani 1 1 d . . . . .
C10 C 0.53489(7) 0.86968(19) 0.60080(7) 0.0566(4) Uani 1 1 d . . . . .
C12 C 0.66010(7) 0.66091(18) 0.49934(7) 0.0541(3) Uani 1 1 d . . . . .
C14 C 0.78869(7) 0.61689(18) 0.48490(7) 0.0560(4) Uani 1 1 d . . . . .
C16 C 0.62973(7) 0.74543(19) 0.54681(7) 0.0564(4) Uani 1 1 d . . . . .
C18 C 0.84942(7) 0.76695(19) 0.56431(7) 0.0589(4) Uani 1 1 d . . . . .
C20 C 0.47617(7) 0.94072(18) 0.58312(8) 0.0590(4) Uani 1 1 d . . . . .
H20 H 0.459770 0.921282 0.543977 0.071 Uiso 1 1 calc R U . . .
C22 C 0.62127(7) 0.58310(19) 0.45218(7) 0.0599(4) Uani 1 1 d . . . . .
C24 C 0.68955(8) 0.62878(19) 0.35764(7) 0.0616(4) Uani 1 1 d . . . . .
H24 H 0.706176 0.725840 0.373979 0.074 Uiso 1 1 calc R U . . .
C3 C 0.62554(9) 0.3854(2) 0.36710(8) 0.0696(4) Uani 1 1 d . . . . .
H3 H 0.597623 0.319153 0.389977 0.083 Uiso 1 1 calc R U . . .
C13 C 0.79813(8) 0.9198(2) 0.64571(8) 0.0662(4) Uani 1 1 d . . . . .
H13 H 0.760762 0.957645 0.665470 0.079 Uiso 1 1 calc R U . . .
C7 C 0.44205(8) 1.0396(2) 0.62305(9) 0.0715(5) Uani 1 1 d . . . . .
H7 H 0.402592 1.086143 0.610927 0.086 Uiso 1 1 calc R U . . .
C15 C 0.91041(8) 0.8073(2) 0.58655(9) 0.0729(5) Uani 1 1 d . . . . .
H15 H 0.947933 0.770419 0.566798 0.087 Uiso 1 1 calc R U . . .
C2 C 0.55873(8) 0.8988(3) 0.65897(8) 0.0761(5) Uani 1 1 d . . . . .
H2 H 0.597876 0.851441 0.671491 0.091 Uiso 1 1 calc R U . . .
C17 C 0.70612(9) 0.5808(2) 0.29881(8) 0.0730(5) Uani 1 1 d . . . . .
H17 H 0.732803 0.648123 0.275072 0.088 Uiso 1 1 calc R U . . .
C9 C 0.91485(9) 0.9030(2) 0.63845(10) 0.0798(5) Uani 1 1 d . . . . .
H9 H 0.955779 0.930870 0.653817 0.096 Uiso 1 1 calc R U . . .
C19 C 0.64364(10) 0.3366(2) 0.30921(9) 0.0781(5) Uani 1 1 d . . . . .
H19 H 0.628739 0.237158 0.293402 0.094 Uiso 1 1 calc R U . . .
C5 C 0.85895(9) 0.9589(2) 0.66830(9) 0.0764(5) Uani 1 1 d . . . . .
H5 H 0.862722 1.022662 0.703561 0.092 Uiso 1 1 calc R U . . .
C21 C 0.46598(9) 1.0698(2) 0.68047(10) 0.0814(5) Uani 1 1 d . . . . .
H21 H 0.443184 1.137812 0.707286 0.098 Uiso 1 1 calc R U . . .
C11 C 0.68364(10) 0.4349(2) 0.27498(9) 0.0765(5) Uani 1 1 d . . . . .
H11 H 0.695658 0.403057 0.235570 0.092 Uiso 1 1 calc R U . . .
C23 C 0.52408(9) 0.9989(3) 0.69850(9) 0.0869(6) Uani 1 1 d . . . . .
H23 H 0.540121 1.018643 0.737744 0.104 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
C16 O1 C1 105.39(11) . . ?
C18 O4 C14 124.69(12) . . ?
C10 N1 H1 115.2 . . ?
C16 N1 H1 115.2 . . ?
C16 N1 C10 129.53(14) . . ?
O1 C1 C8 121.86(14) . . ?
C6 C1 O1 111.37(13) . . ?
C6 C1 C8 126.75(13) . . ?
C24 C4 C22 122.84(14) . . ?
C3 C4 C22 117.94(14) . . ?
C3 C4 C24 118.96(15) . . ?
C1 C6 C12 107.14(12) . . ?
C1 C6 C14 118.07(14) . . ?
C12 C6 C14 134.57(14) . . ?
C18 C8 C1 114.11(15) . . ?
C18 C8 C13 119.04(15) . . ?
C13 C8 C1 126.84(14) . . ?
C20 C10 N1 117.21(14) . . ?
C2 C10 N1 123.41(14) . . ?
C2 C10 C20 119.35(15) . . ?
C16 C12 C6 103.89(13) . . ?
C16 C12 C22 120.02(14) . . ?
C22 C12 C6 136.06(13) . . ?
O4 C14 C6 115.18(14) . . ?
O2 C14 O4 116.77(13) . . ?
O2 C14 C6 128.04(15) . . ?
O1 C16 C12 112.18(13) . . ?
N1 C16 O1 118.53(13) . . ?
N1 C16 C12 129.28(15) . . ?
O4 C18 C8 120.95(14) . . ?
C15 C18 O4 117.75(15) . . ?
C15 C18 C8 121.30(17) . . ?
C10 C20 H20 119.8 . . ?
C7 C20 C10 120.48(16) . . ?
C7 C20 H20 119.8 . . ?
O3 C22 C4 117.46(14) . . ?
O3 C22 C12 119.06(14) . . ?
C12 C22 C4 123.42(13) . . ?
C4 C24 H24 120.3 . . ?
C17 C24 C4 119.41(15) . . ?
C17 C24 H24 120.3 . . ?
C4 C3 H3 119.4 . . ?
C19 C3 C4 121.22(16) . . ?
C19 C3 H3 119.4 . . ?
C8 C13 H13 120.1 . . ?
C5 C13 C8 119.73(16) . . ?
C5 C13 H13 120.1 . . ?
C20 C7 H7 119.9 . . ?
C21 C7 C20 120.16(16) . . ?
C21 C7 H7 119.9 . . ?
C18 C15 H15 120.5 . . ?
C9 C15 C18 118.90(17) . . ?
C9 C15 H15 120.5 . . ?
C10 C2 H2 120.2 . . ?
C10 C2 C23 119.54(17) . . ?
C23 C2 H2 120.2 . . ?
C24 C17 H17 119.6 . . ?
C11 C17 C24 120.77(16) . . ?
C11 C17 H17 119.6 . . ?
C15 C9 H9 119.5 . . ?
C15 C9 C5 120.94(17) . . ?
C5 C9 H9 119.5 . . ?
C3 C19 H19 120.2 . . ?
C11 C19 C3 119.63(16) . . ?
C11 C19 H19 120.2 . . ?
C13 C5 C9 120.08(18) . . ?
C13 C5 H5 120.0 . . ?
C9 C5 H5 120.0 . . ?
C7 C21 H21 120.2 . . ?
C7 C21 C23 119.69(17) . . ?
C23 C21 H21 120.2 . . ?
C17 C11 H11 120.0 . . ?
C19 C11 C17 119.96(17) . . ?
C19 C11 H11 120.0 . . ?
C2 C23 H23 119.6 . . ?
C21 C23 C2 120.76(18) . . ?
C21 C23 H23 119.6 . . ?
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 1.3776(16) . ?
O1 C16 1.3649(19) . ?
O4 C14 1.3921(19) . ?
O4 C18 1.379(2) . ?
O2 C14 1.1976(19) . ?
O3 C22 1.2407(19) . ?
N1 H1 0.8600 . ?
N1 C10 1.413(2) . ?
N1 C16 1.3327(18) . ?
C1 C6 1.354(2) . ?
C1 C8 1.417(2) . ?
C4 C22 1.483(2) . ?
C4 C24 1.383(2) . ?
C4 C3 1.382(2) . ?
C6 C12 1.449(2) . ?
C6 C14 1.4511(19) . ?
C8 C18 1.393(2) . ?
C8 C13 1.399(2) . ?
C10 C20 1.388(2) . ?
C10 C2 1.379(2) . ?
C12 C16 1.388(2) . ?
C12 C22 1.445(2) . ?
C18 C15 1.379(2) . ?
C20 H20 0.9300 . ?
C20 C7 1.375(2) . ?
C24 H24 0.9300 . ?
C24 C17 1.382(2) . ?
C3 H3 0.9300 . ?
C3 C19 1.373(2) . ?
C13 H13 0.9300 . ?
C13 C5 1.376(2) . ?
C7 H7 0.9300 . ?
C7 C21 1.366(3) . ?
C15 H15 0.9300 . ?
C15 C9 1.376(3) . ?
C2 H2 0.9300 . ?
C2 C23 1.380(3) . ?
C17 H17 0.9300 . ?
C17 C11 1.374(2) . ?
C9 H9 0.9300 . ?
C9 C5 1.392(3) . ?
C19 H19 0.9300 . ?
C19 C11 1.365(3) . ?
C5 H5 0.9300 . ?
C21 H21 0.9300 . ?
C21 C23 1.379(3) . ?
C11 H11 0.9300 . ?
C23 H23 0.9300 . ?
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 C6 C12 -0.55(15) . . . . ?
O1 C1 C6 C14 -175.91(11) . . . . ?
O1 C1 C8 C18 179.43(12) . . . . ?
O1 C1 C8 C13 -1.7(2) . . . . ?
O4 C18 C15 C9 -179.67(15) . . . . ?
N1 C10 C20 C7 178.28(14) . . . . ?
N1 C10 C2 C23 -178.39(17) . . . . ?
C1 O1 C16 N1 179.49(13) . . . . ?
C1 O1 C16 C12 -1.94(15) . . . . ?
C1 C6 C12 C16 -0.61(15) . . . . ?
C1 C6 C12 C22 177.30(16) . . . . ?
C1 C6 C14 O4 -5.49(19) . . . . ?
C1 C6 C14 O2 173.48(15) . . . . ?
C1 C8 C18 O4 -1.53(19) . . . . ?
C1 C8 C18 C15 177.95(14) . . . . ?
C1 C8 C13 C5 -178.44(15) . . . . ?
C4 C24 C17 C11 -2.2(3) . . . . ?
C4 C3 C19 C11 -1.2(3) . . . . ?
C6 C1 C8 C18 0.7(2) . . . . ?
C6 C1 C8 C13 179.59(14) . . . . ?
C6 C12 C16 O1 1.60(16) . . . . ?
C6 C12 C16 N1 179.97(15) . . . . ?
C6 C12 C22 O3 167.80(16) . . . . ?
C6 C12 C22 C4 -15.1(3) . . . . ?
C8 C1 C6 C12 178.25(13) . . . . ?
C8 C1 C6 C14 2.9(2) . . . . ?
C8 C18 C15 C9 0.8(2) . . . . ?
C8 C13 C5 C9 0.4(3) . . . . ?
C10 N1 C16 O1 8.1(2) . . . . ?
C10 N1 C16 C12 -170.22(15) . . . . ?
C10 C20 C7 C21 0.4(2) . . . . ?
C10 C2 C23 C21 0.0(3) . . . . ?
C12 C6 C14 O4 -179.26(13) . . . . ?
C12 C6 C14 O2 -0.3(3) . . . . ?
C14 O4 C18 C8 -1.5(2) . . . . ?
C14 O4 C18 C15 178.99(14) . . . . ?
C14 C6 C12 C16 173.63(15) . . . . ?
C14 C6 C12 C22 -8.5(3) . . . . ?
C16 O1 C1 C6 1.51(15) . . . . ?
C16 O1 C1 C8 -177.37(12) . . . . ?
C16 N1 C10 C20 144.06(17) . . . . ?
C16 N1 C10 C2 -37.9(3) . . . . ?
C16 C12 C22 O3 -14.5(2) . . . . ?
C16 C12 C22 C4 162.60(14) . . . . ?
C18 O4 C14 O2 -174.05(13) . . . . ?
C18 O4 C14 C6 5.04(19) . . . . ?
C18 C8 C13 C5 0.4(2) . . . . ?
C18 C15 C9 C5 0.0(3) . . . . ?
C20 C10 C2 C23 -0.4(3) . . . . ?
C20 C7 C21 C23 -0.8(3) . . . . ?
C22 C4 C24 C17 -172.17(15) . . . . ?
C22 C4 C3 C19 174.18(16) . . . . ?
C22 C12 C16 O1 -176.73(12) . . . . ?
C22 C12 C16 N1 1.6(2) . . . . ?
C24 C4 C22 O3 132.98(17) . . . . ?
C24 C4 C22 C12 -44.2(2) . . . . ?
C24 C4 C3 C19 0.0(3) . . . . ?
C24 C17 C11 C19 1.0(3) . . . . ?
C3 C4 C22 O3 -41.0(2) . . . . ?
C3 C4 C22 C12 141.82(15) . . . . ?
C3 C4 C24 C17 1.7(2) . . . . ?
C3 C19 C11 C17 0.7(3) . . . . ?
C13 C8 C18 O4 179.52(13) . . . . ?
C13 C8 C18 C15 -1.0(2) . . . . ?
C7 C21 C23 C2 0.6(3) . . . . ?
C15 C9 C5 C13 -0.6(3) . . . . ?
C2 C10 C20 C7 0.2(2) . . . . ?
