Crystal engineering of co-crystal of nicotinic acid and pyrogallol: an experimental and theoretical electron density analysis
Iqbal, Alia; Mehmood, Arshad; Noureen, Sajida; Lecomte, Claude; Ahmed, Maqsood; Acta Crystallographica Section B 77 (2021) 1035–1047; doi:10.1107/S2052520621009124

data_2108895
_publ_section_title
;
 Crystal engineering of co-crystal of nicotinic acid and pyrogallol: an
 experimental and theoretical electron density analysis
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              1035
_journal_page_last               1047
_journal_paper_doi               10.1107/S2052520621009124
_journal_volume                  77
_journal_year                    2021
_chemical_formula_moiety         'C6 H5 N O2, C6 H6 O3'
_chemical_formula_sum            'C12 H11 N O5'
_chemical_formula_weight         249.22
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-12-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.6648(4)
_cell_length_b                   11.9321(3)
_cell_length_c                   12.9678(4)
_cell_measurement_reflns_used    2780
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      52.2
_cell_measurement_theta_min      2.27
_cell_volume                     2114.40(10)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II'
_diffrn_measurement_method       'omega and phi scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            101259
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         52.201
_diffrn_reflns_theta_min         2.266
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.7503
_exptl_absorpt_correction_T_min  0.6752
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0673 before and 0.0563 after correction.
The Ratio of minimum to maximum transmission is 0.8999.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.286
_exptl_crystal_size_min          0.243
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 7550 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.33(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         23980
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0565P)^2^+0.0520P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1080
_reflns_Friedel_coverage         0.927
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                18901
_reflns_number_total             23980
_reflns_threshold_expression     '>2.0 sigma(I)'
_cod_data_source_file            px5041sup1.cif
_cod_data_source_block           IAM_SHELX
_cod_database_code               2108895
_publcif_datablock.id            {b6945dbc-22ad-4a98-89e7-d5db92dd06c6}
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.958
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), N2(H2), C3(H3), C4(H4), C5(H5A), C7(H7A), C9(H9A), C10(H10A),
  C11(H11), C15(H15), C16(H16), C17(H17), C21(H21), C22(H22), C23(H23)
2.b Idealised tetrahedral OH refined as rotating group with stretchable bonds:
 O5(H5), O6(H6), O7(H7), O8(H8), O9(H9), O10(H10)
;
_shelx_res_checksum              22167
_shelx_hkl_checksum              24697
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
_publcif_funding_html
;
;