Short C–H⋯F interactions involving the 2,5-difluorobenzene group: understanding the role of fluorine in aggregation and complex C–F/C–H disorder in a 2 × 6 isomer grid
Mocilac, P.; Osman, I. A.; Gallagher, J. F.; CrystEngComm 18 (2016) 5764–; doi:10.1039/C6CE00795C

data_7225602
_publ_section_title
;
 Short C--H&#x22EF;F interactions involving the 2,5-difluorobenzene group:
 understanding the role of fluorine in aggregation and complex C--F/C--H
 disorder in a 2 \\times 6 isomer grid
;
_journal_issue                   30
_journal_name_full               CrystEngComm
_journal_page_first              5764
_journal_paper_doi               10.1039/C6CE00795C
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C13 H9 F2 N O'
_chemical_formula_sum            'C13 H9 F2 N O'
_chemical_formula_weight         233.21
_chemical_melting_point          402
_chemical_name_systematic        '(26_F2 or 11-018)'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-02-14 deposited with the CCDC.
2016-06-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1031(18)
_cell_length_b                   21.838(3)
_cell_length_c                   4.8875(6)
_cell_measurement_reflns_used    2293
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      3.44
_cell_volume                     1078.3(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-14/7
_computing_structure_refinement
'SHELXL97 and SHELXL-14/7 (Sheldrick, 2008) & SORTX (McArdle, 1995)'
_computing_structure_solution    'SHELXS-14/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      294(1)
_diffrn_detector_area_resol_mean 16.056
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            7275
_diffrn_reflns_point_group_measured_fraction_full 0.838
_diffrn_reflns_point_group_measured_fraction_max 0.800
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.454
_diffrn_reflns_theta_min         3.450
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Empirical - ABSPACK'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       Needle
_exptl_crystal_F_000             480
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-hexane'
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details
;
Flack x from 298 quotients (Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack   -0.8(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.848
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1980
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.848
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0336
_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^)+(0.0311P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0599
_refine_ls_wR_factor_ref         0.0667
_reflns_Friedel_coverage         0.480
_reflns_Friedel_fraction_full    0.634
_reflns_Friedel_fraction_max     0.588
_reflns_number_gt                1187
_reflns_number_total             1980
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c6ce00795c2.cif
_cod_data_source_block           26_F2_294K
_cod_depositor_comments
'Adding full bibliography for 7225595--7225606.cif.'
_cod_database_code               7225602
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.942
_shelx_estimated_absorpt_t_max   0.994
_shelx_res_checksum              20532