Fluconazolium oxalate: synthesis and structural characterization of a highly soluble crystalline form
Owoyemi, Bolaji C. Dayo; da Silva, Cecilia C. P.; Diniz, Luan F.; Souza, Matheus S.; Ellena, Javier; Carneiro, Renato L.; CrystEngComm 21 (2019) 1114–; doi:10.1039/C8CE01729H

data_7232077
_publ_section_title
;
 Fluconazolium oxalate: synthesis and structural characterization of a
 highly soluble crystalline form
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              1114
_journal_paper_doi               10.1039/C8CE01729H
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C13 H13 F2 N6 O, C2 H O4'
_chemical_formula_sum            'C15 H14 F2 N6 O5'
_chemical_formula_weight         396.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-04-19 deposited with the CCDC.
2018-12-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.566(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6109(6)
_cell_length_b                   14.9140(18)
_cell_length_c                   20.848(3)
_cell_measurement_reflns_used    1456
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.88
_cell_measurement_theta_min      2.73
_cell_volume                     1733.1(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_av_unetI/netI     0.0860
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            15398
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_min         1.967
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1100 before and 0.0469 after correction. The Ratio of minimum to maximum transmission is 0.8866. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3939
_refine_ls_number_restraints     69
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1326
_refine_ls_R_factor_gt           0.0551
_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^)+(0.0604P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1280
_refine_ls_wR_factor_ref         0.1581
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1893
_reflns_number_total             3939
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce01729h1.cif
_cod_data_source_block           mo_fluco_0m
_cod_depositor_comments          'Adding full bibliography for 7232077.cif.'
_cod_original_cell_volume        1733.1(3)
_cod_database_code               7232077
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2. Rigid body (RIGU) restrains
 C10, C9, C8, C13, C12, C11
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O3, O2, O4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O5, O3, O2, O4, C15, C14
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Fixed Sof: O5(0.45) O5'(0.55)
4.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), N3(H3), C12(H12), C13(H13), C7(H7), C5(H5), C10(H10)
4.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4A)
;
_olex2_submission_special_instructions 'No special instructions were received'