#------------------------------------------------------------------------------
#$Date: 2021-06-05 07:42:12 +0300 (Sat, 05 Jun 2021) $
#$Revision: 265823 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/29/7242970.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_7242970
loop_
_publ_author_name
'Lin, Huawei'
'Yang, Huimin'
'Gong, Qi'
'Luo, Shan'
'Gu, Jing'
'Cao, Xiaoqun'
'Mao, Biming'
'Ge, Yanqing'
'Yuan, Chunhao'
_publ_section_title
;
 Construction of cyclopentane-fused coumarins via DBU-catalyzed [3+2]
 cycloaddition of 3-homoacyl coumarins with cyclic 1-azadienes
;
_journal_issue                   33
_journal_name_full               'RSC Advances'
_journal_page_first              20118
_journal_page_last               20122
_journal_paper_doi               10.1039/D1RA03387E
_journal_volume                  11
_journal_year                    2021
_chemical_formula_sum            'C32 H23 N O6 S'
_chemical_formula_weight         549.57
_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   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-03-29 deposited with the CCDC.	2021-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                114.381(3)
_cell_angle_beta                 99.000(3)
_cell_angle_gamma                101.915(3)
_cell_formula_units_Z            2
_cell_length_a                   10.5537(10)
_cell_length_b                   11.0474(11)
_cell_length_c                   13.2402(13)
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      54.01
_cell_measurement_theta_min      3.31
_cell_volume                     1324.2(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_av_unetI/netI     0.0679
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13998
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        52.989
_diffrn_reflns_theta_max         52.989
_diffrn_reflns_theta_min         3.312
_exptl_absorpt_coefficient_mu    0.967
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4655
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0758
_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)+(0.1696P)²+0.2560P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2104
_refine_ls_wR_factor_ref         0.2158
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4296
_reflns_number_total             4655
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra03387e2.cif
_cod_data_source_block           20190909li_ZNZ5256_31_5_0m_a
_cod_database_code               7242970
_shelx_shelxl_version_number     2018/3
_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_min   0.861
_shelx_estimated_absorpt_t_max   0.901
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
C1 C -0.1134(2) 0.1396(2) 0.6040(2) 0.0427(5) Uani 1 1 d . . . . .
H1 H -0.124458 0.187722 0.559730 0.051 Uiso 1 1 calc R U . . .
C2 C -0.2256(3) 0.0578(3) 0.6134(2) 0.0536(7) Uani 1 1 d . . . . .
H2 H -0.313241 0.048964 0.574533 0.064 Uiso 1 1 calc R U . . .
C3 C -0.2099(3) -0.0105(3) 0.6792(2) 0.0538(7) Uani 1 1 d . . . . .
H3 H -0.286757 -0.065727 0.686080 0.065 Uiso 1 1 calc R U . . .
C4 C -0.0825(3) 0.0014(3) 0.7351(2) 0.0561(7) Uani 1 1 d . . . . .
H4 H -0.071926 -0.044841 0.781051 0.067 Uiso 1 1 calc R U . . .
C5 C 0.0291(3) 0.0799(3) 0.7243(2) 0.0488(6) Uani 1 1 d . . . . .
H5 H 0.116632 0.085997 0.761229 0.059 Uiso 1 1 calc R U . . .
C6 C 0.0139(2) 0.1508(2) 0.65898(17) 0.0355(5) Uani 1 1 d . . . . .
C7 C 0.1372(2) 0.2343(2) 0.64863(17) 0.0332(5) Uani 1 1 d . . . . .
C8 C 0.1387(2) 0.3694(2) 0.64156(16) 0.0288(4) Uani 1 1 d . . . . .
H8 H 0.047813 0.383405 0.638503 0.035 Uiso 1 1 calc R U . . .
C9 C 0.18647(19) 0.3736(2) 0.53707(15) 0.0289(4) Uani 1 1 d . . . . .
H9 H 0.214735 0.288587 0.498456 0.035 Uiso 1 1 calc R U . . .
C10 C 0.0728(2) 0.3712(2) 0.45083(16) 0.0320(5) Uani 1 1 d . . . . .
C11 C 0.2303(2) 0.5260(2) 0.41107(17) 0.0328(5) Uani 1 1 d . . . . .
C12 C 0.2459(2) 0.5776(3) 0.33278(19) 0.0432(6) Uani 1 1 d . . . . .
H12 H 0.173822 0.549890 0.267336 0.052 Uiso 1 1 calc R U . . .
C13 C 0.3683(3) 0.6700(3) 0.3517(2) 0.0446(6) Uani 1 1 d . . . . .
H13 H 0.380462 0.706031 0.298812 0.054 Uiso 1 1 calc R U . . .
C14 C 0.4731(2) 0.7101(2) 0.44713(18) 0.0383(5) Uani 1 1 d . . . . .
H14 H 0.556576 0.774442 0.460372 0.046 Uiso 1 1 calc R U . . .
C15 C 0.4558(2) 0.6558(2) 0.52345(17) 0.0333(5) Uani 1 1 d . . . . .
H15 H 0.528531 0.681978 0.587975 0.040 Uiso 1 1 calc R U . . .
C16 C 0.3327(2) 0.5631(2) 0.50683(16) 0.0288(4) Uani 1 1 d . . . . .
C17 C 0.31127(19) 0.5019(2) 0.58772(15) 0.0280(4) Uani 1 1 d . . . . .
H17 H 0.391545 0.471455 0.604442 0.034 Uiso 1 1 calc R U . . .
C18 C 0.29261(18) 0.59865(19) 0.70485(15) 0.0271(4) Uani 1 1 d . . . . .
H18 H 0.220798 0.641757 0.692893 0.033 Uiso 1 1 calc R U . . .
C19 C 0.24548(19) 0.4929(2) 0.74886(15) 0.0286(4) Uani 1 1 d . . . . .
H19 H 0.323213 0.459520 0.766472 0.034 Uiso 1 1 calc R U . . .
C20 C 0.1977(2) 0.5481(2) 0.85622(16) 0.0328(5) Uani 1 1 d . . . . .
C21 C 0.1100(2) 0.6293(2) 0.86959(18) 0.0401(5) Uani 1 1 d . . . . .
H21 H 0.077076 0.649933 0.809423 0.048 Uiso 1 1 calc R U . . .
C22 C 0.0710(3) 0.6798(3) 0.9707(2) 0.0525(7) Uani 1 1 d . . . . .
H22 H 0.011375 0.734840 0.979456 0.063 Uiso 1 1 calc R U . . .
C23 C 0.1185(3) 0.6506(3) 1.0591(2) 0.0577(8) Uani 1 1 d . . . . .
H23 H 0.092564 0.686586 1.128635 0.069 Uiso 1 1 calc R U . . .
C24 C 0.2030(3) 0.5695(3) 1.0458(2) 0.0547(7) Uani 1 1 d . . . . .
H24 H 0.234259 0.548200 1.105909 0.066 Uiso 1 1 calc R U . . .
C25 C 0.2433(2) 0.5183(2) 0.94538(18) 0.0421(5) Uani 1 1 d . . . . .
H25 H 0.302369 0.462576 0.937335 0.051 Uiso 1 1 calc R U . . .
C26 C 0.42389(19) 0.7102(2) 0.78122(15) 0.0289(4) Uani 1 1 d . . . . .
C27 C 0.4464(2) 0.8527(2) 0.79870(16) 0.0307(4) Uani 1 1 d . . . . .
C28 C 0.3596(2) 0.8920(2) 0.73439(19) 0.0358(5) Uani 1 1 d . . . . .
H28 H 0.281823 0.823534 0.676347 0.043 Uiso 1 1 calc R U . . .
C29 C 0.3863(2) 1.0291(3) 0.7547(2) 0.0442(6) Uani 1 1 d . . . . .
H29 H 0.328359 1.054389 0.709633 0.053 Uiso 1 1 calc R U . . .
C30 C 0.4980(3) 1.1296(2) 0.8414(2) 0.0469(6) Uani 1 1 d . . . . .
H30 H 0.514617 1.224122 0.856418 0.056 Uiso 1 1 calc R U . . .
C31 C 0.5852(2) 1.0952(2) 0.9060(2) 0.0428(5) Uani 1 1 d . . . . .
H31 H 0.661410 1.164623 0.965284 0.051 Uiso 1 1 calc R U . . .
C32 C 0.5593(2) 0.9574(2) 0.88256(17) 0.0348(5) Uani 1 1 d . . . . .
N1 N 0.51387(17) 0.66863(19) 0.82534(15) 0.0348(4) Uani 1 1 d . . . . .
O1 O 0.64790(15) 0.92513(16) 0.95069(13) 0.0416(4) Uani 1 1 d . . . . .
O2 O 0.73500(17) 0.7697(2) 0.80478(17) 0.0524(5) Uani 1 1 d . . . . .
O3 O 0.72390(18) 0.7502(2) 0.98090(18) 0.0609(5) Uani 1 1 d . . . . .
O4 O 0.10246(15) 0.43674(17) 0.38693(12) 0.0389(4) Uani 1 1 d . . . . .
O5 O -0.04314(15) 0.31000(18) 0.43172(13) 0.0439(4) Uani 1 1 d . . . . .
O6 O 0.23890(17) 0.19920(18) 0.64926(16) 0.0463(4) Uani 1 1 d . . . . .
S1 S 0.66669(5) 0.77362(6) 0.88970(5) 0.0404(2) Uani 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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 '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 C1 C2 120.0(2) . . ?
C6 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.6(2) . . ?
C1 C6 C7 121.87(19) . . ?
C5 C6 C7 118.5(2) . . ?
O6 C7 C6 121.08(19) . . ?
O6 C7 C8 118.85(18) . . ?
C6 C7 C8 120.03(18) . . ?
C7 C8 C19 108.64(15) . . ?
C7 C8 C9 112.58(16) . . ?
C19 C8 C9 104.40(15) . . ?
C7 C8 H8 110.4 . . ?
C19 C8 H8 110.4 . . ?
C9 C8 H8 110.4 . . ?
C10 C9 C17 115.25(16) . . ?
C10 C9 C8 110.55(16) . . ?
C17 C9 C8 106.26(15) . . ?
C10 C9 H9 108.2 . . ?
C17 C9 H9 108.2 . . ?
C8 C9 H9 108.2 . . ?
O5 C10 O4 117.17(18) . . ?
O5 C10 C9 124.03(18) . . ?
O4 C10 C9 118.74(17) . . ?
C16 C11 C12 122.3(2) . . ?
C16 C11 O4 122.73(17) . . ?
C12 C11 O4 114.94(19) . . ?
C13 C12 C11 118.9(2) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.7(2) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 121.0(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C11 C16 C15 117.66(18) . . ?
C11 C16 C17 120.13(18) . . ?
C15 C16 C17 122.20(18) . . ?
C16 C17 C9 113.56(15) . . ?
C16 C17 C18 116.83(16) . . ?
C9 C17 C18 103.61(14) . . ?
C16 C17 H17 107.5 . . ?
C9 C17 H17 107.5 . . ?
C18 C17 H17 107.5 . . ?
C26 C18 C19 113.70(15) . . ?
C26 C18 C17 110.40(15) . . ?
C19 C18 C17 100.76(14) . . ?
C26 C18 H18 110.5 . . ?
C19 C18 H18 110.5 . . ?
C17 C18 H18 110.5 . . ?
C20 C19 C18 115.61(16) . . ?
C20 C19 C8 114.84(15) . . ?
C18 C19 C8 103.32(14) . . ?
C20 C19 H19 107.5 . . ?
C18 C19 H19 107.5 . . ?
C8 C19 H19 107.5 . . ?
C25 C20 C21 118.9(2) . . ?
C25 C20 C19 119.0(2) . . ?
C21 C20 C19 122.14(18) . . ?
C22 C21 C20 120.0(2) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.5(3) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 119.7(2) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 120.6(2) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C20 120.3(2) . . ?
C24 C25 H25 119.9 . . ?
C20 C25 H25 119.9 . . ?
N1 C26 C27 123.46(18) . . ?
N1 C26 C18 115.61(18) . . ?
C27 C26 C18 120.88(17) . . ?
C32 C27 C28 117.23(19) . . ?
C32 C27 C26 119.51(18) . . ?
C28 C27 C26 123.26(18) . . ?
C29 C28 C27 120.7(2) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C28 C29 C30 119.7(2) . . ?
C28 C29 H29 120.2 . . ?
C30 C29 H29 120.2 . . ?
C31 C30 C29 121.3(2) . . ?
C31 C30 H30 119.4 . . ?
C29 C30 H30 119.4 . . ?
C30 C31 C32 118.4(2) . . ?
C30 C31 H31 120.8 . . ?
C32 C31 H31 120.8 . . ?
C31 C32 C27 122.7(2) . . ?
C31 C32 O1 117.38(19) . . ?
C27 C32 O1 119.84(19) . . ?
C26 N1 S1 119.18(15) . . ?
C32 O1 S1 116.12(13) . . ?
C10 O4 C11 122.36(16) . . ?
O3 S1 O2 119.90(12) . . ?
O3 S1 O1 105.02(11) . . ?
O2 S1 O1 108.18(10) . . ?
O3 S1 N1 109.64(10) . . ?
O2 S1 N1 108.61(10) . . ?
O1 S1 N1 104.36(9) . . ?
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
C1 C6 1.379(3) . ?
C1 C2 1.389(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.380(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.398(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.492(3) . ?
C7 O6 1.213(3) . ?
C7 C8 1.531(3) . ?
C8 C19 1.554(3) . ?
C8 C9 1.560(2) . ?
C8 H8 1.0000 . ?
C9 C10 1.509(3) . ?
C9 C17 1.536(3) . ?
C9 H9 1.0000 . ?
C10 O5 1.200(3) . ?
C10 O4 1.354(2) . ?
C11 C16 1.379(3) . ?
C11 C12 1.388(3) . ?
C11 O4 1.397(2) . ?
C12 C13 1.384(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.399(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.506(2) . ?
C17 C18 1.549(2) . ?
C17 H17 1.0000 . ?
C18 C26 1.513(3) . ?
C18 C19 1.537(2) . ?
C18 H18 1.0000 . ?
C19 C20 1.511(3) . ?
C19 H19 1.0000 . ?
C20 C25 1.394(3) . ?
C20 C21 1.399(3) . ?
C21 C22 1.386(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.386(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.370(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.387(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 N1 1.297(3) . ?
C26 C27 1.455(3) . ?
C27 C32 1.395(3) . ?
C27 C28 1.406(3) . ?
C28 C29 1.382(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.387(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.374(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.379(3) . ?
C31 H31 0.9500 . ?
C32 O1 1.398(3) . ?
N1 S1 1.6291(17) . ?
O1 S1 1.6013(18) . ?
O2 S1 1.4185(18) . ?
O3 S1 1.4089(18) . ?
