Synthesis and crystal structure of 5-(8-(((5-carboxypentyl)ammonio)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxy-3-nitrobenzenesulfonate monohydrate, C22H24N2O12S
Chen, Hai-Lin; Wang, Yan-Ping; Pan, Li-Wei; Wei, Zheng; Tang, Ling-Chan; Zeitschrift für Kristallographie - New Crystal Structures 238 (2023) 217–219; doi:10.1515/ncrs-2022-0532

data_8107399
_publ_section_title
;
 Synthesis and crystal structure of
 5-(8-(((5-carboxypentyl)ammonio)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxy-3-nitrobenzenesulfonate
 monohydrate, C22H24N2O12S
;
_journal_issue                   2
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              217
_journal_page_last               219
_journal_paper_doi               10.1515/ncrs-2022-0532
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C22 H22 N2 O11 S, H2 O'
_chemical_formula_sum            'C22 H24 N2 O12 S'
_chemical_formula_weight         540.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   38.8080(3)
_cell_length_b                   33.3993(3)
_cell_length_c                   7.16660(10)
_cell_measurement_reflns_used    19505
_cell_measurement_temperature    99.98(11)
_cell_measurement_theta_max      75.5520
_cell_measurement_theta_min      3.5170
_cell_volume                     9289.06(17)
_computing_cell_refinement       'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)[1]'
_computing_data_collection       'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)[1]'
_computing_data_reduction        'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)[1]'
_computing_molecular_graphics    'Diamond 3.2 [2]'
_computing_publication_material  'SHELXL 2018/3 (Sheldrick, 2015)[3]'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)[3]'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)[4]'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(11)
_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 0.993
_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     13.00 109.00   0.50    0.17    --   39.45  52.00 167.00  192
  2  \w    147.00 173.00   0.50    0.68    --  111.82  52.00 167.00   52
  3  \w     94.00 121.00   0.50    0.68    --  111.82  52.00 167.00   54
  4  \w     84.00 110.00   0.50    0.68    --  111.82  45.00  90.00   52
  5  \w    113.00 173.00   0.50    0.68    --  111.82  45.00  90.00  120
  6  \w    134.00 172.00   0.50    0.68    --  111.82  30.00 120.00   76
  7  \w     86.00 111.00   0.50    0.68    --  111.82  30.00 120.00   50
  8  \w     27.00  83.00   0.50    0.68    --  111.82   0.00   0.00  112
  9  \w    100.00 175.00   0.50    0.68    --  111.82   0.00   0.00  150
 10  \w     88.00 175.00   0.50    0.68    --  111.82  61.00-150.00  174
 11  \w     96.00 152.00   0.50    0.68    --  111.82  30.00-150.00  112
 12  \w    -62.00 -25.00   0.50    0.68    --  -62.00  52.00 167.00   74
 13  \w    -21.00   7.00   0.50    0.17    --  -39.45  52.00 167.00   56
 14  \w    -33.00  -7.00   0.50    0.68    --  -62.00  45.00  30.00   52
 15  \w    -16.00  20.00   0.50    0.68    --  -62.00  15.00 -30.00   72
 16  \w    -14.00  15.00   0.50    0.68    --  -62.00  15.00   0.00   58
 17  \w    -55.00 -14.00   0.50    0.17    --  -39.45 -52.00  22.00   82
 18  \w    -90.00 -64.00   0.50    0.17    --  -39.45 125.00 -30.00   52
 19  \w    -97.00 -36.00   0.50    0.17    --  -39.45 125.00-120.00  122
 20  \w   -101.00 -61.00   0.50    0.68    --  -62.00 -52.00  22.00   80
 21  \w   -137.00-106.00   0.50    0.68    --  -62.00 -52.00  22.00   62
 22  \w   -116.00 -89.00   0.50    0.17    --  -39.45 -52.00  22.00   54
 23  \w   -141.00 -90.00   0.50    0.68    --  -62.00-111.00 120.00  102
 24  \w   -135.00 -90.00   0.50    0.68    --  -62.00-111.00 150.00   90
 25  \w     61.00  87.00   0.50    0.68    --  111.82 -77.00   0.00   52
 26  \w     38.00  68.00   0.50    0.68    --  111.82 -61.00  90.00   60
 27  \w     38.00  65.00   0.50    0.68    --  111.82 -61.00   0.00   54
 28  \w     42.00  68.00   0.50    0.68    --  111.82 -61.00 -60.00   52
 29  \w     41.00  68.00   0.50    0.68    --  111.82 -61.00 -90.00   54
 30  \w    -37.00  30.00   0.50    0.17    --   39.45 -52.00  22.00  134
 31  \w    148.00 174.00   0.50    0.68    --  111.82 111.00   0.00   52
 32  \w     38.00  65.00   0.50    0.68    --  111.82 -61.00-150.00   54
 33  \w     39.00  96.00   0.50    0.68    --  111.82 -77.00-180.00  114
 34  \w     73.00 103.00   0.50    0.68    --  111.82 -94.00 -60.00   60
 35  \w     80.00 106.00   0.50    0.68    --  111.82-111.00-150.00   52
 36  \w     35.00  73.00   0.50    0.68    --  111.82-111.00-150.00   76
 37  \w     67.00 108.00   0.50    0.68    --  111.82-111.00 -60.00   82
 38  \w     83.00 108.00   0.50    0.68    --  111.82-111.00  30.00   50
 39  \w     80.00 106.00   0.50    0.68    --  111.82-111.00  90.00   52
 40  \w     32.00  71.00   0.50    0.68    --  111.82-111.00  30.00   78
 41  \w     44.00  92.00   0.50    0.68    --  111.82 -94.00   0.00   96
 42  \w     36.00  62.00   0.50    0.68    --  111.82-111.00 -60.00   52
 43  \w     32.00  60.00   0.50    0.68    --  111.82-111.00-180.00   56
 44  \w     79.00 105.00   0.50    0.68    --  111.82-111.00-180.00   52
 45  \w     25.00  98.00   0.50    0.17    --   39.45-125.00 -90.00  146
 46  \w     33.00  59.00   0.50    0.68    --  111.82 -94.00 -60.00   52
 47  \w     33.00  99.00   0.50    0.68    --  111.82 -94.00  60.00  132
 48  \w     32.00  96.00   0.50    0.68    --  111.82 -94.00 120.00  128
;
_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      0.0024352000
_diffrn_orient_matrix_UB_12      0.0133303000
_diffrn_orient_matrix_UB_13      -0.2053365000
_diffrn_orient_matrix_UB_21      -0.0249251000
_diffrn_orient_matrix_UB_22      0.0348459000
_diffrn_orient_matrix_UB_23      0.0404618000
_diffrn_orient_matrix_UB_31      0.0308040000
_diffrn_orient_matrix_UB_32      0.0271323000
_diffrn_orient_matrix_UB_33      0.0489052000
_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  0.0256
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            22287
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.069
_diffrn_reflns_theta_min         3.492
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.887
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87676
_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            yellow
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_description       needle
_exptl_crystal_F_000             4512
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Flack x determined using 2058 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.006(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         4722
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0432
_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/[\s^2^(Fo^2^)+(0.0794P)^2^+21.3871P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1223
_reflns_Friedel_coverage         0.816
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                4677
_reflns_number_total             4722
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0532_suppl.cif
_cod_data_source_block           tlc-100k
_cod_database_code               8107399
_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,H,H,H)
  groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 C19-C18 \\sim C19A-C18A
 with sigma of 0.02
 N2-C17 \\sim N2-C17A
 with sigma of 0.02
 C18-C17 \\sim C18A-C17A
 with sigma of 0.02
 C20-C19 \\sim C20-C19A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C17) = Uanis(C17A)
Uanis(C18) = Uanis(C18A)
Uanis(C19) = Uanis(C19A)
4. Others
 Sof(C17A)=Sof(H17C)=Sof(H17D)=Sof(C18A)=Sof(H18C)=Sof(H18D)=Sof(C19A)=
 Sof(H19C)=Sof(H19D)=Sof(H20C)=Sof(H20D)=Sof(H2BC)=Sof(H2BD)=1-FVAR(1)
 Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(C19)=Sof(H19A)=
 Sof(H19B)=Sof(H20A)=Sof(H20B)=Sof(H2AA)=Sof(H2AB)=FVAR(1)
5.a Riding coordinates:
 O12(H12A,H12B)
5.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C17A(H17C,H17D), C18(H18A,H18B), C18A(H18C,
 H18D), C19(H19A,H19B), C19A(H19C,H19D), C20(H20A,H20B), C20(H20C,H20D),
 C21(H21A,H21B), N2(H2AA,H2AB), N2(H2BC,H2BD)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C9(H9), C11(H11), C15(H15)
5.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4), O11(H11A)
;
_shelx_res_checksum              49933
_shelx_hkl_checksum              39754
_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 1.781
_oxdiff_exptl_absorpt_empirical_full_min 0.576