Synthesis and crystal structure of 1-((7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)methyl)piperidin-1-ium-4-carboxylate monohydrate, C22H22N2O9
Chen, Hai-Lin; Li, Xian; Yao, Dong-Mei; Luo, Ze-Ping; Wang, Yan-Ping; Lan, Jian-Jing; Zeitschrift für Kristallographie - New Crystal Structures 238 (2023) 1215–1217; doi:10.1515/ncrs-2023-0412

data_8107706
_publ_section_title
;
 Synthesis and crystal structure of
 1-((7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)methyl)piperidin-1-ium-4-carboxylate
 monohydrate, C22H22N2O9
;
_journal_issue                   6
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              1215
_journal_page_last               1217
_journal_paper_doi               10.1515/ncrs-2023-0412
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C22 H20 N2 O8, H2 O'
_chemical_formula_sum            'C22 H22 N2 O9'
_chemical_formula_weight         458.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 96.853(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7374(3)
_cell_length_b                   29.1082(11)
_cell_length_c                   8.7595(3)
_cell_measurement_reflns_used    8104
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.0580
_cell_measurement_theta_min      2.4010
_cell_volume                     1958.74(13)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)[1]'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)[1]'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)[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      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.816
_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     35.00  87.00   0.50    0.46    --   10.68-162.00 167.00  104
  2  \w     14.00  39.00   0.50    0.46    --   10.68-117.00 -42.00   50
  3  \w    -27.00  23.00   0.50    0.46    --  -11.15 -77.00-150.00  100
  4  \w    -84.00 -57.00   0.50    0.46    --  -11.15 -77.00-150.00   54
  5  \w     -9.00  23.00   0.50    0.46    --   10.68 -19.00-180.00   64
  6  \w    -79.00 -54.00   0.50    0.46    --  -11.15 162.00-164.00   50
  7  \w    -38.00  64.00   0.50    0.46    --  -11.15  57.00 150.00  204
;
_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      -0.0116554000
_diffrn_orient_matrix_UB_12      0.0240925000
_diffrn_orient_matrix_UB_13      0.0054931000
_diffrn_orient_matrix_UB_21      -0.0334972000
_diffrn_orient_matrix_UB_22      0.0007534000
_diffrn_orient_matrix_UB_23      -0.0789459000
_diffrn_orient_matrix_UB_31      -0.0852123000
_diffrn_orient_matrix_UB_32      -0.0036011000
_diffrn_orient_matrix_UB_33      0.0197686000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.816
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14766
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.816
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.303
_diffrn_reflns_theta_min         2.444
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4372
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0520
_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^)+(0.0770P)^2^+0.6646P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1421
_refine_ls_wR_factor_ref         0.1501
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3383
_reflns_number_total             4372
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0412_suppl_001.cif
_cod_data_source_block           6
_cod_database_code               8107706
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 O5-N1 \\sim O5A-N1
 with sigma of 0.02
 O6-N1 \\sim O6A-N1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O5) = Uanis(O5A)
Uanis(O6) = Uanis(O6A)
4. Others
 Sof(O5A)=Sof(O6A)=1-FVAR(1)
 Sof(O5)=Sof(O6)=FVAR(1)
5.a Free rotating group:
 O9(H9A,H9B)
5.b Ternary CH refined with riding coordinates:
 N2(H2), C19(H19)
5.c Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C20(H20A,H20B), C21(H21A,H21B)
5.d Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C11(H11), C14(H14)
5.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_shelx_res_checksum              30157
_shelx_hkl_checksum              80342
_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 1.328
_oxdiff_exptl_absorpt_empirical_full_min 0.661