Supramolecular heterosynthon assemblies of ortho-phenylenediamine with substituted aromatic carboxylic acids
Mishra, Risha; Pallepogu, Raghavaiah; Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials 74 (2018) 32–; doi:10.1107/S2052520617014299

data_2021917
_publ_section_title
;
 Supramolecular heterosynthon assemblies of ortho-phenylenediamine with
 substituted aromatic carboxylic acids
;
_journal_coeditor_code           EB5067
_journal_issue                   1
_journal_name_full
'Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials'
_journal_page_first              32
_journal_paper_doi               10.1107/S2052520617014299
_journal_volume                  74
_journal_year                    2018
_chemical_formula_moiety         'C7 H4 N O4, C6 H9 N2'
_chemical_formula_sum            'C13 H13 N3 O4'
_chemical_formula_weight         275.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.021(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.881(2)
_cell_length_b                   6.0754(16)
_cell_length_c                   11.995(3)
_cell_measurement_reflns_used    1756
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.29
_cell_volume                     647.1(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298.15
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2914
_diffrn_reflns_point_group_measured_fraction_full 0.892
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         24.978
_diffrn_reflns_theta_min         1.698
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       plate
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 533 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2026
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0499
_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^)+(0.0690P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1256
_reflns_Friedel_coverage         0.644
_reflns_Friedel_fraction_full    0.780
_reflns_Friedel_fraction_max     0.781
_reflns_number_gt                1635
_reflns_number_total             2026
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            eb5067sup1.cif
_cod_data_source_block           OPDPNB
_cod_database_code               2021917
_shelxl_version_number           2012-9
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.960
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N1-H1B
 0.85 with sigma of 0.02
 N1-H1A
 0.89 with sigma of 0.02
 N1-H1C
 0.87 with sigma of 0.02
 N2-H2B
 0.85 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12)
;
_olex2_submission_special_instructions 'No special instructions were received'