Synthesis and crystal structure of 3-(((7-hydroxy-3-(4-hydroxy-3,5-dinitrophenyl)-4-oxo-4H-chromen-8-yl)methyl)(nitroso)amino)propanoic acid, C19H14N4O11
Chen, Hai-Lin; Yao, Dong-Mei; Luo, Ze-Ping; Wang, Yan-Ping; Luo, Li-Sheng; Zeitschrift für Kristallographie - New Crystal Structures 237 (2022) 1029–1031; doi:10.1515/ncrs-2022-0352

data_8107284
_publ_section_title
;
 Synthesis and crystal structure of
 3-(((7-hydroxy-3-(4-hydroxy-3,5-dinitrophenyl)-4-oxo-4H-chromen-8-yl)methyl)(nitroso)amino)propanoic
 acid, C19H14N4O11
;
_journal_issue                   6
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              1029
_journal_page_last               1031
_journal_paper_doi               10.1515/ncrs-2022-0352
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C19 H14 N4 O11'
_chemical_formula_sum            'C19 H14 N4 O11'
_chemical_formula_weight         474.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_cell_angle_alpha                90
_cell_angle_beta                 124.32(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.855(4)
_cell_length_b                   18.214(4)
_cell_length_c                   14.193(3)
_cell_measurement_reflns_used    10619
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.0220
_cell_measurement_theta_min      3.8400
_cell_volume                     3812(2)
_computing_cell_refinement
'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)[1]'
_computing_data_collection
'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)[1]'
_computing_data_reduction
'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)[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      100.01(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 0.987
_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     77.00 103.00   0.50    0.58    --  111.82  77.00-120.00   52
  2  \w    108.00 134.00   0.50    0.58    --  111.82  77.00-120.00   52
  3  \w    124.00 171.00   0.50    0.58    --  111.82  77.00-150.00   94
  4  \w    118.00 169.00   0.50    0.58    --  111.82  77.00-180.00  102
  5  \w     79.00 105.00   0.50    0.58    --  111.82  77.00-180.00   52
  6  \w     77.00 104.00   0.50    0.58    --  111.82  77.00-150.00   54
  7  \w     83.00 172.00   0.50    0.58    --  111.82  61.00 -90.00  178
  8  \w     83.00 156.00   0.50    0.58    --  111.82  61.00-120.00  146
  9  \w     83.00 129.00   0.50    0.58    --  111.82  61.00-150.00   92
 10  \w    126.00 152.00   0.50    0.58    --  111.82  61.00-180.00   52
 11  \w     83.00 108.00   0.50    0.58    --  111.82  61.00-180.00   50
 12  \w    100.00 157.00   0.50    0.58    --  111.82  61.00  30.00  114
 13  \w    150.00 175.00   0.50    0.58    --  111.82  47.00 127.00   50
 14  \w    123.00 174.00   0.50    0.58    --  111.82  77.00 150.00  102
 15  \w    115.00 140.00   0.50    0.58    --  111.82  61.00 150.00   50
 16  \w     83.00 109.00   0.50    0.58    --  111.82  61.00 150.00   52
 17  \w     84.00 116.00   0.50    0.58    --  111.82  47.00 127.00   64
 18  \w     19.00  93.00   0.50    0.14    --   39.20  47.00 127.00  148
 19  \w     85.00 169.00   0.50    0.58    --  111.82  45.00   0.00  168
 20  \w     84.00 167.00   0.50    0.58    --  111.82  45.00 -60.00  166
 21  \w     83.00 126.00   0.50    0.58    --  111.82  45.00-120.00   86
 22  \w    134.00 160.00   0.50    0.58    --  111.82  45.00-150.00   52
 23  \w     83.00 117.00   0.50    0.58    --  111.82  45.00-150.00   68
 24  \w     78.00 104.00   0.50    0.58    --  111.82  30.00-150.00   52
 25  \w    -32.00   6.00   0.50    0.14    --   39.20 -47.00 -21.00   76
 26  \w    -33.00  22.00   0.50    0.14    --   39.20 -19.00   0.00  110
 27  \w    -44.00  22.00   0.50    0.14    --   39.20 -19.00-120.00  132
 28  \w     75.00 107.00   0.50    0.58    --  111.82-111.00 -30.00   64
 29  \w     33.00  88.00   0.50    0.58    --  111.82 -94.00 -30.00  110
 30  \w     33.00 106.00   0.50    0.58    --  111.82-111.00  30.00  146
 31  \w     81.00 106.00   0.50    0.58    --  111.82-111.00  90.00   50
 32  \w     35.00  61.00   0.50    0.58    --  111.82-111.00  90.00   52
 33  \w     38.00 102.00   0.50    0.58    --  111.82 -77.00  30.00  128
 34  \w     38.00  89.00   0.50    0.58    --  111.82 -77.00  90.00  102
 35  \w     53.00  78.00   0.50    0.58    --  111.82 -77.00 150.00   50
 36  \w     38.00  68.00   0.50    0.58    --  111.82 -61.00  90.00   60
 37  \w     51.00 101.00   0.50    0.58    --  111.82 -77.00-150.00  100
 38  \w     40.00  66.00   0.50    0.58    --  111.82 -61.00-180.00   52
 39  \w     38.00  66.00   0.50    0.58    --  111.82 -61.00-150.00   56
 40  \w     42.00  67.00   0.50    0.58    --  111.82 -61.00-120.00   50
 41  \w     40.00  67.00   0.50    0.58    --  111.82 -61.00 120.00   54
 42  \w     42.00  67.00   0.50    0.58    --  111.82 -61.00 150.00   50
 43  \w     52.00  78.00   0.50    0.58    --  111.82 179.00-120.00   52
 44  \w    108.00 143.00   0.50    0.58    --  111.82 179.00-120.00   70
 45  \w     94.00 120.00   0.50    0.58    --  111.82 111.00  90.00   52
 46  \w    127.00 157.00   0.50    0.58    --  111.82 111.00  90.00   60
 47  \w    -23.00  25.00   0.50    0.58    --  -52.00  30.00-150.00   96
 48  \w    -38.00  26.00   0.50    0.58    --  -52.00  30.00 -90.00  128
 49  \w   -124.00 -47.00   0.50    0.14    --  -39.20 179.00-120.00  154
 50  \w    -38.00  -2.00   0.50    0.58    --  -52.00  47.00 127.00   72
 51  \w     -8.00  27.00   0.50    0.14    --  -39.20  47.00 127.00   70
 52  \w   -101.00 -76.00   0.50    0.58    --  -52.00 -47.00 -21.00   50
 53  \w    -88.00 -63.00   0.50    0.14    --  -39.20 -47.00 -21.00   50
 54  \w   -108.00 -68.00   0.50    0.58    --  -52.00 -77.00 -90.00   80
 55  \w   -125.00 -25.00   0.50    0.58    --  -52.00 -61.00-150.00  200
 56  \w   -125.00 -20.00   0.50    0.58    --  -52.00 -77.00-180.00  210
;
_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      0.0992566000
_diffrn_orient_matrix_UB_12      0.0296172000
_diffrn_orient_matrix_UB_13      -0.0073626000
_diffrn_orient_matrix_UB_21      0.0150432000
_diffrn_orient_matrix_UB_22      0.0391425000
_diffrn_orient_matrix_UB_23      0.0918742000
_diffrn_orient_matrix_UB_31      0.0509501000
_diffrn_orient_matrix_UB_32      -0.0689766000
_diffrn_orient_matrix_UB_33      0.0491779000
_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  0.0355
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22401
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.956
_diffrn_reflns_theta_min         3.857
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.207
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_description       block
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         3922
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0639
_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^)+(0.1102P)^2^+6.3459P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1867
_refine_ls_wR_factor_ref         0.1897
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3642
_reflns_number_total             3922
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0352_suppl.cif
_cod_data_source_block           nljx_llx
_cod_original_cell_volume        3812.3(17)
_cod_database_code               8107284
_shelx_estimated_absorpt_t_max   0.859
_shelx_estimated_absorpt_t_min   0.830
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16a,H16b), C17(H17a,H17b), C18(H18a,H18b)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C9(H9), C11(H11), C15(H15)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4), O10(H10)
;
_shelx_res_checksum              28487
_shelx_hkl_checksum              74381
_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 1.731
_oxdiff_exptl_absorpt_empirical_full_min 0.521