Accurate experimental characterization of the labile N–Cl bond in N-chloro-N'-(p-fluorophenyl)-benzamidine crystal at 17.5 K
Destro, Riccardo; Barzaghi, Mario; Soave, Raffaella; Roversi, Pietro; Lo Presti, Leonardo; CrystEngComm  (2022) –; doi:10.1039/D2CE00957A

data_7245343
_publ_section_title
;
 Accurate experimental characterization of the labile N--Cl bond in
 N-chloro-N'-(p-fluorophenyl)-benzamidine crystal at 17.5 K
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00957A
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H10 Cl F N2'
_chemical_formula_sum            'C13 H10 Cl F N2'
_chemical_formula_weight         248.68
_chemical_name_common            NCLBA
_chemical_name_systematic
;
N-chloro-N'-(p-fluorophenyl)-benzamidine
;
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_audit_creation_date             10/06/2022
_audit_creation_method           SHELXL-2014/4
_audit_update_record
;
2022-06-20 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   10.0227(3)
_cell_length_b                   10.0227(3)
_cell_length_c                   9.8795(4)
_cell_measurement_reflns_used    120
_cell_measurement_temperature    17.5(9)
_cell_measurement_theta_max      15.58
_cell_measurement_theta_min      13.25
_cell_volume                     859.48(5)
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996),
Brandenburg, K.; Putz, H. Diamond - Crystal and Molecular Structure
Visualization 3.1d; Crystal
Impact GbR: Bonn, 2006; http://www.crystalimpact.com/diamond.
;
_computing_structure_refinement
;
VALRAY2000 (Stewart, Spackman & Flensburg, 2000)
;
_computing_structure_solution    'SHELXS-2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      17.5(9)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Siemens P1-'
_diffrn_measurement_method       '2\q/\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            27709
_diffrn_reflns_point_group_measured_fraction_full 0.728
_diffrn_reflns_point_group_measured_fraction_max 0.708
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         54.397
_diffrn_reflns_theta_min         2.346
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.323
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       sphere
_exptl_crystal_F_000             384
_exptl_crystal_size_rad          0.25
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.28
_refine_ls_abs_structure_details
;
 Flack x determined using 2780 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.019(12)
_refine_ls_extinction_coef       0.160(8)
_refine_ls_extinction_method     VALRAY2000
_refine_ls_goodness_of_fit_ref   0.9652
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     680
_refine_ls_number_reflns         14309
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9652
_refine_ls_R_factor_all          0.0159
_refine_ls_R_factor_gt           0.0159
_refine_ls_shift/su_max          0.0490
_refine_ls_shift/su_mean         0.0040
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0140
_refine_ls_wR_factor_ref         0.0140
_reflns_Friedel_coverage         0.419
_reflns_Friedel_fraction_full    0.456
_reflns_Friedel_fraction_max     0.419
_reflns_number_gt                14309
_reflns_number_total             14382
_reflns_threshold_expression     'I > 0'
_cod_data_source_file            d2ce00957a3.cif
_cod_data_source_block           NCLBA
_cod_original_cell_volume        859.48(6)
_cod_database_code               7245343
_shelxl_version_number           2014/4
_shelx_res_checksum              58083
_shelx_hkl_checksum              80899