The design of novel metronidazole benzoate structures: exploring stoichiometric diversity
Santiago de Oliveira, Yara; Saraiva Costa, Wendell; Ferreira Borges, Poliana; Silmara Alves de Santana, Maria; Ayala, Alejandro Pedro; Acta Crystallographica Section C 75 (2019) –; doi:10.1107/S2053229619003838

data_2021566
_publ_section_title
;
 The design of novel metronidazole benzoate structures: exploring
 stoichiometric diversity
;
_journal_coeditor_code           JX3032
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229619003838
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C13 H13 N3 O4, C7 H6 O2'
_chemical_formula_moiety         'C13 H13 N3 O4, C7 H6 O2'
_chemical_formula_sum            'C20 H19 N3 O6'
_chemical_formula_weight         397.38
_chemical_name_common
;
Benzoylmetronidazole--benzoic acid (1/1)
;
_chemical_name_systematic
;
2-(2-Methyl-5-nitro-1<i>H</i>-imidazol-1-yl)ethyl benzoate--benzoic acid (1/1)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
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;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
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_cell_length_b                   9.0354(4)
_cell_length_c                   16.5974(8)
_cell_measurement_reflns_used    9997
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      67.97
_cell_measurement_theta_min      5.09
_cell_volume                     1932.42(15)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2012)
;
_computing_data_reduction
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SAINT (Bruker, 2016)
;
_computing_molecular_graphics
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OLEX2 (Dolomanov <i>et al.</i>,  2009),
<i>MERCURY</i> (Version 3.10; Macrae <i>et al.</i>,  2008) and
<i>VEGA</i> (Pedretti <i>et al.</i>, 2004)
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_computing_publication_material
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OLEX2 (Dolomanov <i>et al.</i>,  2009)
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_computing_structure_refinement
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SHELXL2018 (Sheldrick, 2015b)
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_computing_structure_solution
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SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      300.39
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            60527
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.311
_diffrn_reflns_theta_min         3.674
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.860
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            'clear light colourless'
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_exptl_crystal_description       Prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.144
_refine_ls_extinction_coef       0.0027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         3542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0462P)^2^+0.7992P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1297
_reflns_number_gt                2669
_reflns_number_total             3542
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jx3032sup1.cif
_cod_data_source_block           bzmdbzc
_cod_database_code               2021566
_cod_database_fobs_code          2021566
_shelx_estimated_absorpt_t_min   0.546
_shelx_estimated_absorpt_t_max   0.847
_shelx_hkl_checksum              48667
_shelx_res_checksum              91909