Crystal engineering, electron density analysis, and in situ variable temperature studies on co-crystal between nicotinic acid and gallic acid sesquihydrate
Iqbal, Infal; Mehmood, Arshad; Noureen, Sajida; Lecomte, Claude; Ahmed, Maqsood; CrystEngComm 25 (2023) 770–784; doi:10.1039/D2CE01149B

data_7246039
_publ_section_title
;
 Crystal engineering, electron density analysis, and in situ variable
 temperature studies on co-crystal between nicotinic acid and gallic acid
 sesquihydrate
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              770
_journal_page_last               784
_journal_paper_doi               10.1039/D2CE01149B
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C7 H6 O5, C6 H5 N O2, 1.5(H2 O)'
_chemical_formula_sum            'C13 H14 N O8.5'
_chemical_formula_weight         320.25
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2022-05-15
_audit_creation_method
;
FinalCif V89 by Daniel Kratzert, Freiburg 2022,
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2022-05-16 deposited with the CCDC.	2022-12-22 downloaded from the CCDC.
;
_cell_angle_alpha                92.958(9)
_cell_angle_beta                 116.097(10)
_cell_angle_gamma                114.336(10)
_cell_formula_units_Z            4
_cell_length_a                   11.819(3)
_cell_length_b                   11.875(4)
_cell_length_c                   12.418(4)
_cell_measurement_reflns_used    258
_cell_measurement_temperature    310.00
_cell_measurement_theta_max      19.07
_cell_measurement_theta_min      3.10
_cell_volume                     1367.1(8)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      310.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.923
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device       'Four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2173
_diffrn_reflns_av_unetI/netI     0.2829
_diffrn_reflns_Laue_measured_fraction_full 0.923
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7001
_diffrn_reflns_point_group_measured_fraction_full 0.923
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        23.762
_diffrn_reflns_theta_max         23.762
_diffrn_reflns_theta_min         2.314
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.7450
_exptl_absorpt_correction_T_min  0.5480
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0922 before and 0.0636 after correction.
The Ratio of minimum to maximum transmission is 0.7356.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_description       block
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         3861
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.955
_refine_ls_R_factor_all          0.2744
_refine_ls_R_factor_gt           0.1036
_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^)+(0.0476P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1699
_refine_ls_wR_factor_ref         0.2485
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1269
_reflns_number_total             3861
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01149b2.cif
_cod_data_source_block           mo_ga5_infal_ht_2132021_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7246035--7246043.cif.

2024-09-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C26 H28 N2 O17'
_cod_original_formula_weight         640.50
_cod_original_formula_moiety         '2(C7 H6 O5), 2(C6 H5 N O2), 3(H2 O)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        1367.1(7)
_cod_database_code               7246039
_shelx_shelxl_version_number     2018/3
_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, All O(H,H) groups
2.a Free rotating group:
 O16(H16A,H16B), O15(H15A,H15B), O17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1A), C26(H26), C14(H14), C20(H20), C10(H10A), C7(H7), C17(H17),
 C19(H19), C23(H23), C3(H3A), C25(H25), C24(H24), C18(H18)
2.c Idealised tetrahedral OH refined as rotating group:
 O9(H9), O4(H4), O1(H1), O7(H7A), O5(H5), O8(H8), O10(H10), O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cobra Cryo device'
_shelx_res_checksum              1591