The crystal structure of ammonium (E)-4-((4-carboxyphenyl)diazenyl)benzoate, C14H13N3O4
Jian-Ge, Wang; Hua-Rui, Wang; Zeitschrift für Kristallographie - New Crystal Structures 237 (2022) 569–570; doi:10.1515/ncrs-2022-0138

data_8105752
_publ_section_title
;
 The crystal structure of ammonium
 (E)-4-((4-carboxyphenyl)diazenyl)benzoate, C14H13N3O4
;
_journal_issue                   4
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              569
_journal_page_last               570
_journal_paper_doi               10.1515/ncrs-2022-0138
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C14 H9 N2 O4, H4 N'
_chemical_formula_sum            'C14 H13 N3 O4'
_chemical_formula_weight         287.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 96.037(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4188(4)
_cell_length_b                   3.7968(2)
_cell_length_c                   30.2320(18)
_cell_measurement_reflns_used    8788
_cell_measurement_temperature    293.27(10)
_cell_measurement_theta_max      28.2950
_cell_measurement_theta_min      4.0580
_cell_volume                     1303.44(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.27(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.936
_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    -33.00  55.00   1.00   10.00    --  -13.80  38.00-150.00   88
  2  \w    -20.00  25.00   1.00   10.00    --  -13.80 -99.00 -30.00   45
  3  \w    -83.00   5.00   1.00   10.00    --  -13.80 -38.00  30.00   88
  4  \w    -63.00   5.00   1.00   10.00    --  -13.80 117.00  48.00   68
  5  \w     -5.00  64.00   1.00   10.00    --   14.82-117.00 -38.00   69
  6  \w     -2.00  82.00   1.00   10.00    --   14.82  57.00-180.00   84
  7  \w     -4.00  84.00   1.00   10.00    --   14.82  38.00 -60.00   88
  8  \w    -20.00  54.00   1.00   10.00    --   14.82 -99.00  60.00   74
  9  \w     -4.00  84.00   1.00   10.00    --   14.82  38.00   0.00   88
 10  \w    -57.00  44.00   1.00   10.00    --   14.82 -19.00 -30.00  101
 11  \w    -86.00 -35.00   1.00   10.00    --  -13.80-178.00-180.00   51
 12  \w    -86.00 -35.00   1.00   10.00    --  -13.80-178.00 -30.00   51
 13  \w    -20.00  25.00   1.00   10.00    --  -13.80 -99.00-180.00   45
 14  \w    -20.00  54.00   1.00   10.00    --   14.82 -99.00   0.00   74
 15  \w     -2.00  82.00   1.00   10.00    --   14.82  57.00  90.00   84
 16  \w    -20.00  54.00   1.00   10.00    --   14.82 -99.00-120.00   74
 17  \w    -20.00  54.00   1.00   10.00    --   14.82 -99.00  30.00   74
 18  \w    -12.00  59.00   1.00   10.00    --   14.82-108.00-157.93   71
 19  \w    -54.00  84.00   1.00   10.00    --   14.82   0.00-150.00  138
 20  \w    -54.00  84.00   1.00   10.00    --   14.82   0.00-120.00  138
 21  \w    -54.00  -4.00   1.00   10.00    --   14.82   0.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0014124000
_diffrn_orient_matrix_UB_12      -0.0216810000
_diffrn_orient_matrix_UB_13      -0.0465736000
_diffrn_orient_matrix_UB_21      -0.0138894000
_diffrn_orient_matrix_UB_22      0.0595674000
_diffrn_orient_matrix_UB_23      -0.0046162000
_diffrn_orient_matrix_UB_31      0.0931099000
_diffrn_orient_matrix_UB_32      0.0114001000
_diffrn_orient_matrix_UB_33      0.0060057000
_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  0.0527
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            21200
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.438
_diffrn_reflns_theta_min         3.588
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         1529
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0656
_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^)+(0.1178P)^2^+1.1727P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2003
_refine_ls_wR_factor_ref         0.2073
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1324
_reflns_number_total             1529
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0138_suppl.cif
_cod_data_source_block           a
_cod_database_code               8105752
_chemical_oxdiff_formula         c1h1n1o1Zn1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All N(H,H) groups, All O(H) groups
2. Others
 Fixed Sof: H1(0.5)
3.a Riding coordinates:
 O1(H1), N2(H2a,H2b)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
;
_shelx_res_checksum              86690
_shelx_hkl_checksum              35840
_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 1.869
_oxdiff_exptl_absorpt_empirical_full_min 0.363