Effect of Hydrogen Bonds and π...π-interactions on the Crystallization of Phenyl-perfluorophenyl Amides: Understanding the Self-organization of a Cocrystal
Pagliari, Anderson; Meyer, Alexandre R.; Solner, Vanessa; Rosa, Jéssica Maria Luis; Hoerner, Manfredo; Gauze Bonacorso, Helio; Zanatta, Nilo; Martins, Marcos A. P.; CrystEngComm  (2022) –; doi:10.1039/D2CE00231K

data_7245087
_publ_section_title
;
 Effect of Hydrogen Bonds and \p...\p-interactions on the Crystallization
 of Phenyl-perfluorophenyl Amides: Understanding the Self-organization of
 a Cocrystal
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00231K
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C13 H F10 N O, C13 H11 N O'
_chemical_formula_sum            'C26 H12 F10 N2 O2'
_chemical_formula_weight         574.38
_chemical_melting_point          ?
_chemical_name_common            'bis-pentafluorbenzamide N-phenylbenzamide'
_chemical_name_systematic
;
        '2,3,4,5,6-pentafluoro-N-(perfluorophenyl)benzamide N-phenylbenzamide'
;
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_date             2021-11-10T15:53:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2021-11-11 deposited with the CCDC.	2022-06-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.13(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.580(7)
_cell_length_b                   5.800(4)
_cell_length_c                   20.624(17)
_cell_measurement_reflns_used    9617
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.99
_cell_measurement_theta_min      2.33
_cell_measurement_wavelength     0.71073
_cell_volume                     1145.7(15)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER APEX-III'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            44600
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.101
_diffrn_reflns_theta_min         2.327
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.9669
_exptl_absorpt_correction_T_min  0.9164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        SADABS-2016/2 - Bruker AXS area detector scaling and absorption
        correction. Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. &
        Stalke D., J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   none
_exptl_transmission_factor_min   none
_refine_diff_density_max         1.54
_refine_diff_density_min         -0.986
_refine_diff_density_rms         0.108
_refine_ls_abs_structure_details
;
 Flack x determined using 1894 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.18(19)
_refine_ls_extinction_coef       0.016(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     356
_refine_ls_number_reflns         6704
_refine_ls_number_restraints     68
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.1262
_refine_ls_R_factor_gt           0.1047
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0613P)^2^+5.3342P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.223
_refine_ls_wR_factor_ref         0.2359
_reflns_Friedel_coverage         0.83
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                5415
_reflns_number_total             6704
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00231k1.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'none' was changed to '?'
-- the value is undefined or not given.

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        1145.8(15)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7245087
_shelx_estimated_absorpt_t_min   0.916
_shelx_estimated_absorpt_t_max   0.967
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              26582
_shelx_hkl_checksum              54680