#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/48/4034894.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_4034894
loop_
_publ_author_name
'Shi, Juan'
'Kang, Yang'
'Wang, Tao'
'Liang, Yong'
'Zhang, Zunting'
_publ_section_title
;
 Synthesis of Polycyclic Heteroaromatic Coumarins via Photoinduced
 Dehydrogenative Annulation of 4-Phenyl-3-heteroarylcoumarins.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13940
_journal_page_last               13948
_journal_paper_doi               10.1021/acs.joc.8b02290
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C20 H12 O2 S'
_chemical_formula_weight         316.36
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.9342(17)
_cell_length_b                   16.527(4)
_cell_length_c                   21.431(5)
_cell_measurement_reflns_used    9750
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      5.353
_cell_measurement_theta_min      68.250
_cell_volume                     2810.2(11)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            35147
_diffrn_reflns_theta_full        68.61
_diffrn_reflns_theta_max         68.61
_diffrn_reflns_theta_min         5.35
_exptl_absorpt_coefficient_mu    2.102
_exptl_absorpt_correction_T_max  0.5712
_exptl_absorpt_correction_T_min  0.4196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(sadabs; Bruker, 1999)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0662P)²+1.2657P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1201
_reflns_number_gt                2342
_reflns_number_total             2518
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02290_si_003.cif
_cod_data_source_block           s
_cod_original_cell_volume        2810.2(10)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4034894
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.18108(6) 0.08334(3) 0.24829(2) 0.03431(19) Uani 1 1 d .
O1 O 0.39495(19) 0.20772(8) 0.41736(6) 0.0392(4) Uani 1 1 d .
O2 O 0.2419(2) 0.11273(9) 0.37333(7) 0.0459(4) Uani 1 1 d .
C8 C 0.3400(2) 0.21659(11) 0.30641(8) 0.0291(4) Uani 1 1 d .
C13 C 0.4022(2) 0.28167(10) 0.18588(8) 0.0267(4) Uani 1 1 d .
C12 C 0.3131(2) 0.20667(11) 0.19246(8) 0.0285(4) Uani 1 1 d .
C1 C 0.4692(2) 0.33034(11) 0.36086(8) 0.0300(4) Uani 1 1 d .
C6 C 0.4639(3) 0.28455(12) 0.41571(8) 0.0347(4) Uani 1 1 d .
C19 C 0.4238(2) 0.29068(11) 0.30177(8) 0.0277(4) Uani 1 1 d .
C14 C 0.4337(2) 0.31417(11) 0.12599(8) 0.0296(4) Uani 1 1 d .
H14 H 0.3875 0.2876 0.0906 0.036 Uiso 1 1 calc R
C16 C 0.5987(2) 0.41928(10) 0.17058(8) 0.0294(4) Uani 1 1 d .
H16 H 0.6691 0.4653 0.1657 0.035 Uiso 1 1 calc R
C18 C 0.4632(2) 0.32212(10) 0.24015(8) 0.0258(4) Uani 1 1 d .
C15 C 0.5285(2) 0.38257(10) 0.11706(8) 0.0303(4) Uani 1 1 d .
C5 C 0.5238(3) 0.31214(14) 0.47273(9) 0.0424(5) Uani 1 1 d .
H5 H 0.5261 0.2771 0.5078 0.051 Uiso 1 1 calc R
C9 C 0.2835(3) 0.17570(10) 0.25182(8) 0.0287(4) Uani 1 1 d .
C17 C 0.5682(2) 0.39035(11) 0.22929(9) 0.0285(4) Uani 1 1 d .
C4 C 0.5799(3) 0.39075(14) 0.47808(9) 0.0435(5) Uani 1 1 d .
H4 H 0.6262 0.4099 0.5162 0.052 Uiso 1 1 calc R
C20 C 0.5629(3) 0.41697(12) 0.05346(9) 0.0412(5) Uani 1 1 d .
H20C H 0.6774 0.4024 0.0405 0.062 Uiso 1 1 calc R
H20B H 0.5522 0.4760 0.0549 0.062 Uiso 1 1 calc R
H20A H 0.4816 0.3949 0.0235 0.062 Uiso 1 1 calc R
C3 C 0.5675(3) 0.44148(13) 0.42647(9) 0.0408(5) Uani 1 1 d .
H3 H 0.5968 0.4970 0.4305 0.049 Uiso 1 1 calc R
C2 C 0.5132(3) 0.41253(11) 0.36946(9) 0.0340(4) Uani 1 1 d .
C7 C 0.3171(3) 0.17540(12) 0.36620(9) 0.0354(4) Uani 1 1 d .
C10 C 0.1809(3) 0.08664(11) 0.16793(10) 0.0381(5) Uani 1 1 d .
H10 H 0.1345 0.0450 0.1427 0.046 Uiso 1 1 calc R
C11 C 0.2531(3) 0.15400(11) 0.14426(9) 0.0334(4) Uani 1 1 d .
H11 H 0.2629 0.1651 0.1009 0.040 Uiso 1 1 calc R
H17 H 0.628(3) 0.4172(13) 0.2640(11) 0.034(6) Uiso 1 1 d .
H2 H 0.500(3) 0.4502(12) 0.3345(10) 0.026(5) 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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C10 S1 C9 90.92(9)
C7 O1 C6 121.12(14)
C19 C8 C9 120.50(16)
C19 C8 C7 121.98(17)
C9 C8 C7 117.38(17)
C14 C13 C18 120.16(16)
C14 C13 C12 120.32(16)
C18 C13 C12 119.49(15)
C9 C12 C11 112.33(17)
C9 C12 C13 119.42(16)
C11 C12 C13 128.19(16)
C6 C1 C2 114.67(16)
C6 C1 C19 118.37(17)
C2 C1 C19 126.91(16)
O1 C6 C5 114.49(17)
O1 C6 C1 122.02(17)
C5 C6 C1 123.49(19)
C8 C19 C18 118.71(16)
C8 C19 C1 116.48(15)
C18 C19 C1 124.79(17)
C15 C14 C13 122.47(16)
C17 C16 C15 121.81(17)
C17 C18 C13 115.93(15)
C17 C18 C19 123.96(16)
C13 C18 C19 120.04(17)
C14 C15 C16 117.21(16)
C14 C15 C20 122.58(17)
C16 C15 C20 120.19(17)
C4 C5 C6 119.58(18)
C12 C9 C8 121.58(17)
C12 C9 S1 111.33(14)
C8 C9 S1 127.04(13)
C16 C17 C18 122.14(16)
C5 C4 C3 118.62(19)
C2 C3 C4 121.1(2)
C3 C2 C1 121.67(18)
O2 C7 O1 117.24(17)
O2 C7 C8 124.96(19)
O1 C7 C8 117.68(17)
C11 C10 S1 113.65(15)
C10 C11 C12 111.77(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C10 1.723(2)
S1 C9 1.7312(19)
O1 C7 1.367(3)
O1 C6 1.383(2)
O2 C7 1.205(3)
C8 C19 1.397(3)
C8 C9 1.423(3)
C8 C7 1.462(2)
C13 C14 1.414(2)
C13 C18 1.426(2)
C13 C12 1.434(3)
C12 C9 1.391(2)
C12 C11 1.432(3)
C1 C6 1.399(3)
C1 C2 1.415(3)
C1 C19 1.471(2)
C6 C5 1.388(3)
C19 C18 1.453(2)
C14 C15 1.371(3)
C16 C17 1.368(3)
C16 C15 1.412(3)
C18 C17 1.421(3)
C15 C20 1.502(2)
C5 C4 1.378(3)
C4 C3 1.391(3)
C3 C2 1.381(3)
C10 C11 1.351(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168328738
