Synthesis and crystal structure of 5-(8-((3-carboxyazetidin-1-ium-1-yl)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate monohydrate, C20H19NO10S
Chen, Hai-Lin; Huang, Xiu-Xiang; Yao, Dong-Mei; Wang, Yan-Ping; Lu, Xiao-Bing; Zeitschrift für Kristallographie - New Crystal Structures 236 (2021) 1371–1373; doi:10.1515/ncrs-2021-0346

data_8104610
_publ_section_title
;
 Synthesis and crystal structure of
 5-(8-((3-carboxyazetidin-1-ium-1-yl)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate
 monohydrate, C20H19NO10S
;
_journal_issue                   6
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              1371
_journal_page_last               1373
_journal_paper_doi               10.1515/ncrs-2021-0346
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C20 H17 N O9 S, H2 O'
_chemical_formula_sum            'C20 H19 N O10 S'
_chemical_formula_weight         465.42
_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   mixed
_cell_angle_alpha                102.413(2)
_cell_angle_beta                 103.199(2)
_cell_angle_gamma                97.753(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3470(2)
_cell_length_b                   9.6701(2)
_cell_length_c                   12.9523(3)
_cell_measurement_reflns_used    7183
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      75.3590
_cell_measurement_theta_min      3.6020
_cell_volume                     975.26(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     12.00  78.00   0.50    0.05    --   39.20  37.00  60.00  132
  2  \w     85.00 120.00   0.50    0.05    --   39.20  37.00  60.00   70
  3  \w     84.00 109.00   0.50    0.17    --  111.82  45.00 120.00   50
  4  \w    113.00 170.00   0.50    0.17    --  111.82  45.00 120.00  114
  5  \w    131.00 175.00   0.50    0.17    --  111.82  61.00  90.00   88
  6  \w     75.00 174.00   0.50    0.17    --  111.82  30.00  30.00  198
  7  \w     33.00  90.00   0.50    0.17    --  111.82   0.00 -90.00  114
  8  \w     94.00 168.00   0.50    0.17    --  111.82   0.00 -90.00  148
  9  \w    -38.00  20.00   0.50    0.17    --  -62.00  30.00-150.00  116
 10  \w    -25.00  11.00   0.50    0.17    --  -62.00  15.00   0.00   72
 11  \w    -28.00  20.00   0.50    0.17    --  -62.00  15.00 120.00   96
 12  \w    -37.00  17.00   0.50    0.17    --  -62.00  30.00 150.00  108
 13  \w     76.00 109.00   0.50    0.05    --   39.20-158.00 134.00   66
 14  \w     86.00 122.00   0.50    0.17    --  111.82-158.00 134.00   72
 15  \w     69.00 104.00   0.50    0.17    --  111.82-111.00  60.00   70
 16  \w     38.00  66.00   0.50    0.17    --  111.82-111.00 -60.00   56
 17  \w     78.00 109.00   0.50    0.17    --  111.82-118.00 -72.00   62
 18  \w     71.00 102.00   0.50    0.17    --  111.82-111.00 -60.00   62
 19  \w     70.00 107.00   0.50    0.17    --  111.82-111.00-150.00   74
 20  \w     35.00  61.00   0.50    0.17    --  111.82-111.00-150.00   52
 21  \w     13.00  89.00   0.50    0.05    --   39.20-118.00 -72.00  152
 22  \w     63.00  89.00   0.50    0.17    --  111.82 -94.00  90.00   52
 23  \w     79.00 106.00   0.50    0.17    --  111.82-111.00 150.00   54
 24  \w     37.00 101.00   0.50    0.17    --  111.82 -94.00 150.00  128
 25  \w     34.00  60.00   0.50    0.17    --  111.82 -94.00  90.00   52
 26  \w     35.00  89.00   0.50    0.17    --  111.82 -94.00-120.00  108
 27  \w     74.00 102.00   0.50    0.17    --  111.82 -77.00 -60.00   56
 28  \w     64.00 102.00   0.50    0.17    --  111.82 -77.00 -90.00   76
 29  \w     46.00  77.00   0.50    0.17    --  111.82 -77.00-180.00   62
 30  \w     38.00  63.00   0.50    0.17    --  111.82 -61.00 -60.00   50
 31  \w     39.00  65.00   0.50    0.17    --  111.82 -77.00 -60.00   52
 32  \w     38.00  63.00   0.50    0.17    --  111.82 -61.00 -90.00   50
 33  \w     59.00 102.00   0.50    0.17    --  111.82 -77.00  30.00   86
 34  \w     39.00  65.00   0.50    0.17    --  111.82 -61.00  90.00   52
 35  \w     42.00  68.00   0.50    0.17    --  111.82 -61.00 120.00   52
 36  \w     38.00  66.00   0.50    0.17    --  111.82 -61.00  30.00   56
 37  \w     39.00  65.00   0.50    0.17    --  111.82 -61.00   0.00   52
 38  \w     -8.00  19.00   0.50    0.05    --   39.20 -19.00-120.00   54
 39  \w    -42.00  23.00   0.50    0.05    --   39.20 -19.00 -30.00  130
 40  \w     84.00 134.00   0.50    0.17    --  111.82 111.00  60.00  100
 41  \w     82.00 108.00   0.50    0.17    --  111.82 158.00 167.00   52
 42  \w     55.00 110.00   0.50    0.05    --   39.20 158.00 167.00  110
 43  \w    125.00 160.00   0.50    0.17    --  111.82 118.00  13.00   70
 44  \w     97.00 153.00   0.50    0.17    --  111.82 111.00 -30.00  112
 45  \w     87.00 112.00   0.50    0.17    --  111.82 111.00-150.00   50
 46  \w    -95.00 -68.00   0.50    0.05    --  -39.20 -77.00 120.00   54
 47  \w   -111.00 -70.00   0.50    0.05    --  -39.20-158.00 134.00   82
 48  \w   -122.00 -97.00   0.50    0.17    --  -62.00-158.00 134.00   50
 49  \w   -138.00-113.00   0.50    0.17    --  -62.00-118.00 -72.00   50
 50  \w    -44.00  -4.00   0.50    0.05    --  -39.20 -77.00 120.00   80
 51  \w    -88.00 -63.00   0.50    0.17    --  -62.00 118.00  13.00   50
 52  \w    -59.00 -33.00   0.50    0.05    --  -39.20 118.00  13.00   52
 53  \w    -95.00 -70.00   0.50    0.05    --  -39.20 158.00 167.00   50
 54  \w   -110.00 -85.00   0.50    0.17    --  -62.00 158.00 167.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0132876000
_diffrn_orient_matrix_UB_12      0.0335826000
_diffrn_orient_matrix_UB_13      -0.1090893000
_diffrn_orient_matrix_UB_21      0.0812483000
_diffrn_orient_matrix_UB_22      0.1577688000
_diffrn_orient_matrix_UB_23      0.0614490000
_diffrn_orient_matrix_UB_31      0.1748078000
_diffrn_orient_matrix_UB_32      -0.0403202000
_diffrn_orient_matrix_UB_33      0.0168671000
_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  0.0291
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10313
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.765
_diffrn_reflns_theta_min         3.625
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.049
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.64a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_description       plate
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3921
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0439
_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/[\s^2^(Fo^2^)+(0.0549P)^2^+0.6407P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3522
_reflns_number_total             3921
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0346_suppl.cif
_cod_data_source_block           nchl-chl8.24-ding-100k
_cod_database_code               8104610
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 N1-C16 \\sim N1A-C16
 with sigma of 0.02
 N1-C19 \\sim N1A-C19
 with sigma of 0.02
 N1-C17 \\sim N1A-C17
 with sigma of 0.02
 O9-C20 \\sim O9A-C20A
 with sigma of 0.02
 O9-C18 \\sim O9A-C18
 with sigma of 0.04
 O8-C20 \\sim O8A-C20A
 with sigma of 0.02
 C18-C20 \\sim C18-C20A
 with sigma of 0.02
 O8-C18 \\sim O8A-C18
 with sigma of 0.04
 O9-O8 \\sim O9A-O8A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(N1) = Uanis(N1A)
Uanis(O8) = Uanis(O8A)
Uanis(O9) = Uanis(O9A)
Uanis(C20) = Uanis(C20A)
4. Others
 Sof(H16C)=Sof(H16D)=Sof(H17C)=Sof(H17D)=Sof(H19C)=Sof(H19D)=Sof(N1A)=
 Sof(H1AA)=1-FVAR(1)
 Sof(H16A)=Sof(H16B)=Sof(H17A)=Sof(H17B)=Sof(H19A)=Sof(H19B)=Sof(N1)=Sof(H1A)=
 FVAR(1)
 Sof(H18A)=Sof(O8A)=Sof(H8A)=Sof(O9A)=Sof(C20A)=1-FVAR(2)
 Sof(H18)=Sof(O8)=Sof(O9)=Sof(H9A)=Sof(C20)=FVAR(2)
5.a Free rotating group:
 O10(H10A,H10B)
5.b Ternary CH refined with riding coordinates:
 C18(H18), C18(H18A), N1(H1A), N1A(H1AA)
5.c Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C16(H16C,H16D), C17(H17A,H17B), C17(H17C,H17D), C19(H19A,
 H19B), C19(H19C,H19D)
5.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C9(H9), C11(H11), C14(H14), C15(H15)
5.e Tetrahedral OH refined with riding coordinates:
 O8A(H8A)
5.f Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4), O9(H9A)
;
_shelx_res_checksum              93706
_shelx_hkl_checksum              11234
_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 1.701
_oxdiff_exptl_absorpt_empirical_full_min 0.637