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#$Date: 2022-09-16 12:31:29 +0300 (Fri, 16 Sep 2022) $
#$Revision: 277921 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/57/8105786.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_8105786
loop_
_publ_author_name
'Li, Wu-Wu'
'Zheng, Min-Yan'
'Ying, Guo'
'Jiang, Yan-Ping'
'Wang, Qiao'
'Wang, Mei'
'Ji, Min-Xiang'
'Zhang, Yu-Tao'
'Zhang, Zun-Ting'
_publ_section_title
;
 Crystal structure of N-methylanilinium
 5,7-dihydroxy-4-oxo-2-phenyl-4H-chromene-8-sulfonate monohydrate,
 C22H21NO8S
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              581
_journal_page_last               583
_journal_paper_doi               10.1515/ncrs-2018-0585
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C15 H9 O7 S, C7 H10 N, H2 O'
_chemical_formula_sum            'C22 H21 N O8 S'
_chemical_formula_weight         459.46
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                95.004(9)
_cell_angle_beta                 104.918(9)
_cell_angle_gamma                107.323(9)
_cell_formula_units_Z            2
_cell_length_a                   7.095(4)
_cell_length_b                   11.882(7)
_cell_length_c                   13.661(8)
_cell_measurement_reflns_used    748
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.53
_cell_measurement_theta_min      2.48
_cell_volume                     1045.5(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'Bruker APEX-II area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.1006
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6155
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.215
_diffrn_reflns_theta_min         1.568
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       sheet
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.369
_exptl_crystal_size_mid          0.247
_exptl_crystal_size_min          0.105
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.00071(10)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4414
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.1607
_refine_ls_R_factor_gt           0.0627
_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)+(0.0624P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1745
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1826
_reflns_number_total             4414
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0585_suppl.cif
_cod_data_source_block           I
_cod_original_cell_volume        1045.4(11)
_cod_database_code               8105786
_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   0.928
_shelx_estimated_absorpt_t_max   0.979
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
S1 S 0.43830(18) 0.07589(9) 0.30954(8) 0.0551(3) Uani 1 1 d . . . . .
N1 N 1.0179(5) 0.7518(3) 0.5597(3) 0.0659(10) Uani 1 1 d . . . . .
H1A H 1.152674 0.766244 0.587640 0.079 Uiso 1 1 calc R U . . .
H1B H 0.955239 0.728706 0.606784 0.079 Uiso 1 1 calc R U . . .
O1 O 0.5038(5) 0.0609(2) 0.41532(19) 0.0778(10) Uani 1 1 d . . . . .
O2 O 0.6022(4) 0.1626(2) 0.2840(2) 0.0712(9) Uani 1 1 d . . . . .
O3 O 0.2453(4) 0.1003(2) 0.2835(2) 0.0738(9) Uani 1 1 d . . . . .
O4 O 0.4771(5) -0.1625(2) 0.3806(2) 0.0637(8) Uani 1 1 d D . . . .
H4 H 0.487(7) -0.103(3) 0.4255(17) 0.096 Uiso 1 1 d D U . . .
O5 O 0.3026(4) 0.0166(2) 0.08827(18) 0.0459(7) Uani 1 1 d . . . . .
O6 O 0.1265(4) -0.2999(2) -0.10445(19) 0.0609(8) Uani 1 1 d . . . . .
O7 O 0.2194(5) -0.3996(2) 0.0552(2) 0.0672(9) Uani 1 1 d . . . . .
H7 H 0.171560 -0.396233 -0.005454 0.101 Uiso 1 1 calc R U . . .
O8 O 0.8422(6) 0.6926(3) 0.7104(3) 0.0740(10) Uani 1 1 d D . . . .
C1 C 0.3887(6) -0.0650(3) 0.2362(3) 0.0433(9) Uani 1 1 d . . . . .
C2 C 0.4073(6) -0.1657(4) 0.2787(3) 0.0472(10) Uani 1 1 d . . . . .
C3 C 0.3533(6) -0.2767(3) 0.2166(3) 0.0543(11) Uani 1 1 d . . . . .
H3 H 0.369499 -0.341778 0.246694 0.065 Uiso 1 1 calc R U . . .
C4 C 0.2772(6) -0.2910(3) 0.1126(3) 0.0471(10) Uani 1 1 d . . . . .
C5 C 0.2619(5) -0.1913(3) 0.0647(3) 0.0428(9) Uani 1 1 d . . . . .
C6 C 0.3185(5) -0.0819(3) 0.1292(3) 0.0402(9) Uani 1 1 d . . . . .
C7 C 0.1870(6) -0.2014(3) -0.0445(3) 0.0474(10) Uani 1 1 d . . . . .
C8 C 0.1890(6) -0.0917(3) -0.0800(3) 0.0494(10) Uani 1 1 d . . . . .
H8 H 0.152948 -0.091893 -0.150459 0.059 Uiso 1 1 calc R U . . .
C9 C 0.2409(5) 0.0114(3) -0.0154(3) 0.0443(10) Uani 1 1 d . . . . .
C10 C 0.2447(5) 0.1295(3) -0.0406(3) 0.0432(9) Uani 1 1 d . . . . .
C11 C 0.1707(6) 0.1419(4) -0.1425(3) 0.0527(11) Uani 1 1 d . . . . .
H11 H 0.119295 0.075104 -0.194632 0.063 Uiso 1 1 calc R U . . .
C12 C 0.1731(6) 0.2526(4) -0.1666(3) 0.0613(12) Uani 1 1 d . . . . .
H12 H 0.128141 0.260979 -0.234912 0.074 Uiso 1 1 calc R U . . .
C13 C 0.2418(7) 0.3503(4) -0.0894(4) 0.0641(12) Uani 1 1 d . . . . .
H13 H 0.241270 0.424688 -0.105444 0.077 Uiso 1 1 calc R U . . .
C14 C 0.3114(7) 0.3386(4) 0.0113(4) 0.0652(12) Uani 1 1 d . . . . .
H14 H 0.357511 0.405178 0.063223 0.078 Uiso 1 1 calc R U . . .
C15 C 0.3135(6) 0.2290(3) 0.0360(3) 0.0567(11) Uani 1 1 d . . . . .
H15 H 0.361450 0.221899 0.104493 0.068 Uiso 1 1 calc R U . . .
C16 C 0.7869(11) 0.4699(5) 0.3083(4) 0.0866(17) Uani 1 1 d . . . . .
H16 H 0.735797 0.406195 0.253408 0.104 Uiso 1 1 calc R U . . .
C17 C 0.6586(9) 0.4978(5) 0.3566(4) 0.0917(17) Uani 1 1 d . . . . .
H17 H 0.517976 0.454332 0.333403 0.110 Uiso 1 1 calc R U . . .
C18 C 0.7342(8) 0.5907(4) 0.4406(4) 0.0778(14) Uani 1 1 d . . . . .
H18 H 0.646328 0.608942 0.474714 0.093 Uiso 1 1 calc R U . . .
C19 C 0.9403(7) 0.6544(4) 0.4717(3) 0.0572(11) Uani 1 1 d . . . . .
C20 C 1.0713(8) 0.6290(4) 0.4228(4) 0.0720(13) Uani 1 1 d . . . . .
H20 H 1.211575 0.673432 0.444458 0.086 Uiso 1 1 calc R U . . .
C21 C 0.9907(10) 0.5358(5) 0.3406(4) 0.0852(16) Uani 1 1 d . . . . .
H21 H 1.078210 0.517501 0.306318 0.102 Uiso 1 1 calc R U . . .
C22 C 0.9848(7) 0.8652(4) 0.5327(4) 0.0796(15) Uani 1 1 d . . . . .
H22A H 1.065221 0.895924 0.488158 0.119 Uiso 1 1 calc R U . . .
H22B H 1.026982 0.923302 0.594372 0.119 Uiso 1 1 calc R U . . .
H22C H 0.840933 0.849301 0.498133 0.119 Uiso 1 1 calc R U . . .
H8A H 0.904(6) 0.690(4) 0.7694(15) 0.078(17) Uiso 1 1 d D . . . .
H8B H 0.794(9) 0.745(4) 0.722(5) 0.15(3) Uiso 1 1 d D . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
O1 S1 O3 112.7(2) . .
O1 S1 O2 111.17(19) . .
O3 S1 O2 113.3(2) . .
O1 S1 C1 104.88(18) . .
O3 S1 C1 106.22(17) . .
O2 S1 C1 108.01(18) . .
C19 N1 C22 113.4(3) . .
C19 N1 H1A 108.9 . .
C22 N1 H1A 108.9 . .
C19 N1 H1B 108.9 . .
C22 N1 H1B 108.9 . .
H1A N1 H1B 107.7 . .
C2 O4 H4 122(2) . .
C9 O5 C6 121.1(3) . .
C4 O7 H7 109.5 . .
H8A O8 H8B 100(5) . .
C6 C1 C2 116.3(3) . .
C6 C1 S1 119.6(3) . .
C2 C1 S1 124.0(3) . .
O4 C2 C3 115.8(4) . .
O4 C2 C1 123.0(3) . .
C3 C2 C1 121.3(3) . .
C4 C3 C2 120.8(4) . .
C4 C3 H3 119.6 . .
C2 C3 H3 119.6 . .
O7 C4 C3 119.5(4) . .
O7 C4 C5 120.0(3) . .
C3 C4 C5 120.5(3) . .
C6 C5 C4 116.9(3) . .
C6 C5 C7 120.6(3) . .
C4 C5 C7 122.5(3) . .
O5 C6 C5 119.9(3) . .
O5 C6 C1 116.0(3) . .
C5 C6 C1 124.1(3) . .
O6 C7 C8 122.8(3) . .
O6 C7 C5 122.0(4) . .
C8 C7 C5 115.2(3) . .
C9 C8 C7 122.3(4) . .
C9 C8 H8 118.8 . .
C7 C8 H8 118.8 . .
C8 C9 O5 120.7(3) . .
C8 C9 C10 128.3(3) . .
O5 C9 C10 111.0(3) . .
C15 C10 C11 118.9(3) . .
C15 C10 C9 120.9(3) . .
C11 C10 C9 120.2(3) . .
C12 C11 C10 120.4(4) . .
C12 C11 H11 119.8 . .
C10 C11 H11 119.8 . .
C13 C12 C11 119.8(4) . .
C13 C12 H12 120.1 . .
C11 C12 H12 120.1 . .
C12 C13 C14 120.2(4) . .
C12 C13 H13 119.9 . .
C14 C13 H13 119.9 . .
C13 C14 C15 120.5(4) . .
C13 C14 H14 119.8 . .
C15 C14 H14 119.8 . .
C14 C15 C10 120.2(4) . .
C14 C15 H15 119.9 . .
C10 C15 H15 119.9 . .
C17 C16 C21 119.3(5) . .
C17 C16 H16 120.3 . .
C21 C16 H16 120.3 . .
C16 C17 C18 120.8(5) . .
C16 C17 H17 119.6 . .
C18 C17 H17 119.6 . .
C19 C18 C17 118.3(5) . .
C19 C18 H18 120.9 . .
C17 C18 H18 120.9 . .
C20 C19 C18 121.7(4) . .
C20 C19 N1 120.4(4) . .
C18 C19 N1 117.8(4) . .
C19 C20 C21 118.2(5) . .
C19 C20 H20 120.9 . .
C21 C20 H20 120.9 . .
C16 C21 C20 121.6(5) . .
C16 C21 H21 119.2 . .
C20 C21 H21 119.2 . .
N1 C22 H22A 109.5 . .
N1 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
N1 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.444(3) .
S1 O3 1.446(3) .
S1 O2 1.447(3) .
S1 C1 1.763(4) .
N1 C19 1.458(5) .
N1 C22 1.497(5) .
N1 H1A 0.8900 .
N1 H1B 0.8900 .
O4 C2 1.345(4) .
O4 H4 0.871(17) .
O5 C9 1.361(4) .
O5 C6 1.362(4) .
O6 C7 1.255(4) .
O7 C4 1.339(4) .
O7 H7 0.8200 .
O8 H8A 0.822(10) .
O8 H8B 0.821(10) .
C1 C6 1.393(5) .
C1 C2 1.401(5) .
C2 C3 1.393(5) .
C3 C4 1.359(5) .
C3 H3 0.9300 .
C4 C5 1.421(5) .
C5 C6 1.390(5) .
C5 C7 1.430(5) .
C7 C8 1.427(5) .
C8 C9 1.338(5) .
C8 H8 0.9300 .
C9 C10 1.468(5) .
C10 C15 1.382(5) .
C10 C11 1.392(5) .
C11 C12 1.380(5) .
C11 H11 0.9300 .
C12 C13 1.371(5) .
C12 H12 0.9300 .
C13 C14 1.371(6) .
C13 H13 0.9300 .
C14 C15 1.377(5) .
C14 H14 0.9300 .
C15 H15 0.9300 .
C16 C17 1.351(7) .
C16 C21 1.355(7) .
C16 H16 0.9300 .
C17 C18 1.390(6) .
C17 H17 0.9300 .
C18 C19 1.363(6) .
C18 H18 0.9300 .
C19 C20 1.361(6) .
C20 C21 1.374(6) .
C20 H20 0.9300 .
C21 H21 0.9300 .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
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
O1 S1 C1 C6 179.0(3) . . . .
O3 S1 C1 C6 59.5(3) . . . .
O2 S1 C1 C6 -62.3(3) . . . .
O1 S1 C1 C2 1.7(4) . . . .
O3 S1 C1 C2 -117.8(3) . . . .
O2 S1 C1 C2 120.4(3) . . . .
C6 C1 C2 O4 178.6(3) . . . .
S1 C1 C2 O4 -4.0(5) . . . .
C6 C1 C2 C3 -1.5(5) . . . .
S1 C1 C2 C3 175.9(3) . . . .
O4 C2 C3 C4 178.7(4) . . . .
C1 C2 C3 C4 -1.2(6) . . . .
C2 C3 C4 O7 -177.5(4) . . . .
C2 C3 C4 C5 3.5(6) . . . .
O7 C4 C5 C6 178.1(3) . . . .
C3 C4 C5 C6 -3.0(5) . . . .
O7 C4 C5 C7 -0.4(6) . . . .
C3 C4 C5 C7 178.6(4) . . . .
C9 O5 C6 C5 -3.1(5) . . . .
C9 O5 C6 C1 178.3(3) . . . .
C4 C5 C6 O5 -178.3(3) . . . .
C7 C5 C6 O5 0.1(5) . . . .
C4 C5 C6 C1 0.2(5) . . . .
C7 C5 C6 C1 178.6(3) . . . .
C2 C1 C6 O5 -179.4(3) . . . .
S1 C1 C6 O5 3.1(4) . . . .
C2 C1 C6 C5 2.0(5) . . . .
S1 C1 C6 C5 -175.5(3) . . . .
C6 C5 C7 O6 -176.9(3) . . . .
C4 C5 C7 O6 1.4(6) . . . .
C6 C5 C7 C8 3.9(5) . . . .
C4 C5 C7 C8 -177.8(3) . . . .
O6 C7 C8 C9 175.5(4) . . . .
C5 C7 C8 C9 -5.3(6) . . . .
C7 C8 C9 O5 2.6(6) . . . .
C7 C8 C9 C10 -178.3(3) . . . .
C6 O5 C9 C8 1.8(5) . . . .
C6 O5 C9 C10 -177.4(3) . . . .
C8 C9 C10 C15 -176.4(4) . . . .
O5 C9 C10 C15 2.7(5) . . . .
C8 C9 C10 C11 6.2(6) . . . .
O5 C9 C10 C11 -174.6(3) . . . .
C15 C10 C11 C12 2.3(6) . . . .
C9 C10 C11 C12 179.7(3) . . . .
C10 C11 C12 C13 -2.3(6) . . . .
C11 C12 C13 C14 1.1(7) . . . .
C12 C13 C14 C15 0.2(7) . . . .
C13 C14 C15 C10 -0.2(6) . . . .
C11 C10 C15 C14 -1.0(6) . . . .
C9 C10 C15 C14 -178.4(4) . . . .
C21 C16 C17 C18 -1.9(8) . . . .
C16 C17 C18 C19 1.3(8) . . . .
C17 C18 C19 C20 -0.1(7) . . . .
C17 C18 C19 N1 179.9(4) . . . .
C22 N1 C19 C20 98.8(5) . . . .
C22 N1 C19 C18 -81.2(5) . . . .
C18 C19 C20 C21 -0.4(7) . . . .
N1 C19 C20 C21 179.6(4) . . . .
C17 C16 C21 C20 1.3(8) . . . .
C19 C20 C21 C16 -0.2(7) . . . .
