#------------------------------------------------------------------------------
#$Date: 2022-03-04 11:20:38 +0200 (Fri, 04 Mar 2022) $
#$Revision: 273322 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/46/8104621.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_8104621
loop_
_publ_author_name
'Gong, Yi-Xia'
'Geng, Yi-Ding'
'Zhou, Shu-Jing'
'Wang, Gui-Yan'
_publ_section_title
;
 The crystal structure of
 1-[5-(2-fluorophenyl)-1-(pyridine-3-sulfonyl)-1H-pyrrol-3-yl]-N-methylmethanaminium
 3-carboxyprop-2-enoate, C21H20FN3O6S
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              911
_journal_page_last               913
_journal_paper_doi               10.1515/ncrs-2021-0146
_journal_volume                  236
_journal_year                    2021
_chemical_formula_sum            'C21 H20 F N3 O6 S'
_chemical_formula_weight         461.46
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 92.5000(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8502(4)
_cell_length_b                   7.9892(4)
_cell_length_c                   34.9707(19)
_cell_measurement_reflns_used    3506
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.70
_cell_measurement_theta_min      2.33
_cell_volume                     2191.2(2)
_computing_cell_refinement       'CrysAlisPro, Ver. 38.43 [1]'
_computing_data_collection       'CrysAlisPro, Ver. 38.43 [1]'
_computing_data_reduction        'CrysAlisPro, Ver. 38.43 [1]'
_computing_molecular_graphics    'Diamond 4.0 [4]'
_computing_publication_material  'SHELXL-2014/7 [3]'
_computing_structure_refinement  'SHELXL-2014/7 [3]'
_computing_structure_solution    'SHELXT  [2]'
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2711
_diffrn_detector_type            EOS
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            13924
_diffrn_reflns_theta_full        25.28
_diffrn_reflns_theta_max         25.28
_diffrn_reflns_theta_min         1.17
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.9650
_exptl_absorpt_correction_T_min  0.9575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.687
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3987
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0502
_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)+(0.0578P)²+1.8136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1361
_reflns_number_gt                3246
_reflns_number_total             3987
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_j_ncrs-2021-0146_suppl.cif
_cod_data_source_block           d4
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               8104621
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1A F 0.0874(6) -0.1222(6) 0.12937(14) 0.0684(17) Uani 0.410(5) 1 d P A 1
F1B F -0.1513(4) 0.2482(4) 0.21207(9) 0.0730(12) Uani 0.590(5) 1 d P A 2
C1 C -0.0984(4) 0.0956(4) 0.20479(9) 0.0522(7) Uani 1 1 d . . .
H1 H -0.1327 0.2033 0.2109 0.063 Uiso 0.410(5) 1 calc PR A 1
C2 C -0.1182(4) -0.0301(5) 0.23108(10) 0.0667(9) Uani 1 1 d . A .
H2 H -0.1632 -0.0071 0.2547 0.080 Uiso 1 1 calc R . .
C3 C -0.0709(4) -0.1886(5) 0.22208(11) 0.0694(10) Uani 1 1 d . . .
H3 H -0.0837 -0.2743 0.2397 0.083 Uiso 1 1 calc R A .
C4 C -0.0041(4) -0.2238(4) 0.18700(11) 0.0649(9) Uani 1 1 d . A .
H4 H 0.0265 -0.3327 0.1808 0.078 Uiso 1 1 calc R . .
C5 C 0.0164(4) -0.0955(4) 0.16141(9) 0.0501(7) Uani 1 1 d . . .
H5 H 0.0623 -0.1188 0.1379 0.060 Uiso 0.590(5) 1 calc PR A 2
C6 C -0.0296(3) 0.0681(3) 0.16969(8) 0.0401(6) Uani 1 1 d . A .
C7 C -0.0062(3) 0.2029(3) 0.14155(7) 0.0375(6) Uani 1 1 d . . .
C8 C -0.0934(3) 0.2358(3) 0.10806(8) 0.0427(6) Uani 1 1 d . A .
H8 H -0.1891 0.1780 0.0986 0.051 Uiso 1 1 calc R . .
C9 C -0.0153(3) 0.3728(3) 0.08967(7) 0.0382(6) Uani 1 1 d . . .
C10 C 0.1214(3) 0.4203(3) 0.11206(7) 0.0395(6) Uani 1 1 d . A .
H10 H 0.1973 0.5056 0.1067 0.047 Uiso 1 1 calc R . .
C11 C 0.3870(3) 0.1348(3) 0.17531(7) 0.0329(5) Uani 1 1 d . A .
C12 C 0.3723(3) 0.0148(3) 0.20328(7) 0.0423(6) Uani 1 1 d . . .
H12 H 0.3117 0.0356 0.2250 0.051 Uiso 1 1 calc R . .
C13 C 0.4506(4) -0.1366(4) 0.19783(9) 0.0500(7) Uani 1 1 d . . .
H13 H 0.4448 -0.2212 0.2160 0.060 Uiso 1 1 calc R . .
C14 C 0.5377(4) -0.1608(4) 0.16506(9) 0.0522(7) Uani 1 1 d . . .
H14 H 0.5875 -0.2649 0.1615 0.063 Uiso 1 1 calc R . .
C15 C 0.4795(3) 0.1017(3) 0.14341(8) 0.0434(6) Uani 1 1 d . . .
H15 H 0.4890 0.1849 0.1250 0.052 Uiso 1 1 calc R . .
C16 C -0.0695(3) 0.4493(3) 0.05203(7) 0.0428(6) Uani 1 1 d . A .
H16A H -0.0869 0.3612 0.0332 0.051 Uiso 1 1 calc R . .
H16B H 0.0207 0.5215 0.0436 0.051 Uiso 1 1 calc R . .
C17 C -0.2140(4) 0.6948(4) 0.07991(10) 0.0656(9) Uani 1 1 d . A .
H17A H -0.1875 0.6577 0.1056 0.098 Uiso 1 1 calc R . .
H17B H -0.3197 0.7554 0.0792 0.098 Uiso 1 1 calc R . .
H17C H -0.1246 0.7666 0.0717 0.098 Uiso 1 1 calc R . .
C18 C 0.3860(3) 1.3032(3) 0.04141(7) 0.0371(6) Uani 1 1 d . . .
C19 C 0.3044(4) 1.1353(4) 0.03467(9) 0.0521(7) Uani 1 1 d . . .
H19 H 0.1954 1.1310 0.0232 0.063 Uiso 1 1 calc R . .
C20 C 0.3786(4) 0.9975(4) 0.04408(9) 0.0518(7) Uani 1 1 d . . .
H20 H 0.4849 1.0030 0.0568 0.062 Uiso 1 1 calc R . .
C21 C 0.3038(4) 0.8278(4) 0.03573(9) 0.0543(7) Uani 1 1 d U . .
N1 N 0.1284(3) 0.3191(3) 0.14459(6) 0.0372(5) Uani 1 1 d . A .
N2 N -0.2299(3) 0.5488(3) 0.05427(6) 0.0393(5) Uani 1 1 d D . .
H1N H -0.316(3) 0.481(3) 0.0606(8) 0.047 Uiso 1 1 d D . .
H2N H -0.256(3) 0.584(3) 0.0306(6) 0.047 Uiso 1 1 d D . .
N3 N 0.5555(3) -0.0451(3) 0.13799(7) 0.0532(6) Uani 1 1 d . . .
O1 O 0.2070(3) 0.3366(3) 0.21468(5) 0.0558(5) Uani 1 1 d . A .
O2 O 0.3938(3) 0.4586(2) 0.16699(6) 0.0564(5) Uani 1 1 d . A .
O3 O 0.3126(2) 1.4208(2) 0.02315(5) 0.0409(4) Uani 1 1 d . . .
O4 O 0.5120(2) 1.3194(2) 0.06391(5) 0.0479(5) Uani 1 1 d . . .
O5 O 0.1548(3) 0.8072(3) 0.02459(9) 0.0834(8) Uani 1 1 d U . .
O6 O 0.4121(3) 0.7116(3) 0.04125(8) 0.0721(7) Uani 1 1 d D . .
H1O H 0.368(5) 0.613(3) 0.0348(11) 0.087 Uiso 1 1 d D . .
S1 S 0.28475(8) 0.32843(8) 0.178744(18) 0.03953(19) 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 0.0033 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'
F F 0.0171 0.0103 '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
F1B C1 C2 120.1(3) . .
F1B C1 C6 117.3(3) . .
C2 C1 C6 122.6(3) . .
C3 C2 C1 119.0(3) . .
C2 C3 C4 120.8(3) . .
C5 C4 C3 119.0(3) . .
F1A C5 C4 120.6(4) . .
F1A C5 C6 117.5(3) . .
C4 C5 C6 121.8(3) . .
C1 C6 C5 116.8(3) . .
C1 C6 C7 122.8(3) . .
C5 C6 C7 120.4(3) . .
C8 C7 N1 106.7(2) . .
C8 C7 C6 130.1(2) . .
N1 C7 C6 123.1(2) . .
C7 C8 C9 109.2(2) . .
C10 C9 C8 107.5(2) . .
C10 C9 C16 125.6(2) . .
C8 C9 C16 126.9(2) . .
C9 C10 N1 108.1(2) . .
C12 C11 C15 120.2(2) . .
C12 C11 S1 120.9(2) . .
C15 C11 S1 118.89(19) . .
C13 C12 C11 117.5(2) . .
C14 C13 C12 118.8(3) . .
N3 C14 C13 124.5(3) . .
N3 C15 C11 122.5(2) . .
C9 C16 N2 112.3(2) . .
O4 C18 O3 125.2(2) . .
O4 C18 C19 121.0(2) . .
O3 C18 C19 113.8(2) . .
C20 C19 C18 122.8(3) . .
C19 C20 C21 123.8(3) . .
O5 C21 O6 125.0(3) . .
O5 C21 C20 122.8(3) . .
O6 C21 C20 112.2(3) . .
C10 N1 C7 108.5(2) . .
C10 N1 S1 123.84(18) . .
C7 N1 S1 127.40(17) . .
C17 N2 C16 113.9(2) . .
C15 N3 C14 116.5(2) . .
O2 S1 O1 120.67(13) . .
O2 S1 N1 104.98(11) . .
O1 S1 N1 107.61(11) . .
O2 S1 C11 110.12(12) . .
O1 S1 C11 108.47(12) . .
N1 S1 C11 103.61(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1A C5 1.290(5) .
F1B C1 1.316(4) .
C1 C2 1.374(4) .
C1 C6 1.380(4) .
C2 C3 1.360(5) .
C3 C4 1.384(5) .
C4 C5 1.375(4) .
C5 C6 1.390(4) .
C6 C7 1.476(4) .
C7 C8 1.356(4) .
C7 N1 1.407(3) .
C8 C9 1.422(4) .
C9 C10 1.355(4) .
C9 C16 1.496(3) .
C10 N1 1.395(3) .
C11 C12 1.378(3) .
C11 C15 1.383(3) .
C11 S1 1.749(2) .
C12 C13 1.374(4) .
C13 C14 1.373(4) .
C14 N3 1.335(4) .
C15 N3 1.333(3) .
C16 N2 1.493(3) .
C17 N2 1.474(4) .
C18 O4 1.243(3) .
C18 O3 1.261(3) .
C18 C19 1.501(4) .
C19 C20 1.281(4) .
C20 C21 1.501(4) .
C21 O5 1.228(4) .
C21 O6 1.268(4) .
N1 S1 1.676(2) .
O1 S1 1.422(2) .
O2 S1 1.419(2) .
