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#$Date: 2022-08-18 01:39:06 +0300 (Thu, 18 Aug 2022) $
#$Revision: 277291 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/53/7245343.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7245343
loop_
_publ_author_name
'Destro, Riccardo'
'Barzaghi, Mario'
'Soave, Raffaella'
'Roversi, Pietro'
'Lo Presti, Leonardo'
_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       '2θ/ω 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/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/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
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014/4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.089010(4) 0.118410(4) 0.00000 0.006 Uani 1 1 d . . . . .
F1 F -0.16093(3) -0.79418(2) 0.14033(3) 0.010 Uani 1 1 d . . . . .
N1 N 0.21000(2) 0.09832(2) 0.11559(2) 0.006 Uani 1 1 d . . . . .
N2 N 0.05378(2) -0.17098(2) 0.07887(2) 0.007 Uani 1 1 d . . . . .
C1 C 0.17237(2) -0.04499(2) 0.13658(2) 0.005 Uani 1 1 d . . . . .
C2 C 0.27293(2) -0.06165(2) 0.23811(1) 0.005 Uani 1 1 d . . . . .
C3 C 0.21042(2) -0.14320(2) 0.35841(2) 0.006 Uani 1 1 d . . . . .
C4 C 0.30822(2) -0.14947(2) 0.45555(2) 0.007 Uani 1 1 d . . . . .
C5 C 0.46711(2) -0.07459(2) 0.43286(2) 0.007 Uani 1 1 d . . . . .
C6 C 0.52883(2) 0.00486(2) 0.31212(2) 0.007 Uani 1 1 d . . . . .
C7 C 0.43160(2) 0.01124(2) 0.21447(2) 0.006 Uani 1 1 d . . . . .
C8 C 0.00582(2) -0.32821(2) 0.10392(2) 0.006 Uani 1 1 d . . . . .
C9 C 0.10842(2) -0.38432(2) 0.11070(2) 0.006 Uani 1 1 d . . . . .
C10 C 0.05190(2) -0.54201(2) 0.12707(2) 0.007 Uani 1 1 d . . . . .
C11 C -0.10628(2) -0.64050(2) 0.13215(2) 0.007 Uani 1 1 d . . . . .
C12 C -0.21023(2) -0.58765(2) 0.12746(2) 0.007 Uani 1 1 d . . . . .
C13 C -0.15264(2) -0.42974(2) 0.11463(2) 0.007 Uani 1 1 d . . . . .
H3 H 0.08791 -0.19519 0.37584 0.02199 Uani 1 1 d . . . . .
H4 H 0.26149 -0.20430 0.55350 0.02404 Uani 1 1 d . . . . .
H5 H 0.54296 -0.07830 0.50922 0.02811 Uani 1 1 d . . . . .
H6 H 0.65120 0.06041 0.29437 0.02339 Uani 1 1 d . . . . .
H7 H 0.47952 0.07430 0.12175 0.02191 Uani 1 1 d . . . . .
H9 H 0.23098 -0.30812 0.10284 0.02250 Uani 1 1 d . . . . .
H10 H 0.12680 -0.59066 0.13165 0.02961 Uani 1 1 d . . . . .
H12 H -0.33369 -0.66190 0.13358 0.02559 Uani 1 1 d . . . . .
H13 H -0.22885 -0.38414 0.11088 0.02850 Uani 1 1 d . . . . .
H2N H -0.01615 -0.15598 0.01410 0.02115 Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 Cl1 113.238(2) . . ?
C1 N2 C8 127.868(2) . . ?
C1 N2 H2N 118.498 . . ?
C8 N2 H2N 113.496 . . ?
N1 C1 N2 126.517(2) . . ?
N1 C1 C2 112.995(1) . . ?
N2 C1 C2 120.465(2) . . ?
C7 C2 C3 120.448(2) . . ?
C7 C2 C1 119.045(1) . . ?
C3 C2 C1 120.442(2) . . ?
C4 C3 C2 119.381(2) . . ?
C4 C3 H3 121.518 . . ?
C2 C3 H3 119.033 . . ?
C3 C4 C5 120.183(2) . . ?
C3 C4 H4 119.755 . . ?
C5 C4 H4 119.831 . . ?
C6 C5 C4 120.296(2) . . ?
C6 C5 H5 119.717 . . ?
C4 C5 H5 119.987 . . ?
C7 C6 C5 119.782(2) . . ?
C7 C6 H6 120.276 . . ?
C5 C6 H6 119.940 . . ?
C6 C7 C2 119.896(4) . . ?
C6 C7 H7 119.803 . . ?
C2 C7 H7 120.291 . . ?
C9 C8 C13 119.998(2) . . ?
C9 C8 N2 123.041(1) . . ?
C13 C8 N2 116.870(1) . . ?
C10 C9 C8 119.794(3) . . ?
C10 C9 H9 118.967 . . ?
C8 C9 H9 121.237 . . ?
C11 C10 C9 118.816(2) . . ?
C11 C10 H10 118.786 . . ?
C9 C10 H10 122.346 . . ?
F1 C11 C12 118.866(2) . . ?
F1 C11 C10 118.660(1) . . ?
C12 C11 C10 122.469(3) . . ?
C11 C12 C13 118.279(1) . . ?
C11 C12 H12 123.764 . . ?
C13 C12 H12 117.957 . . ?
C12 C13 C8 120.570(1) . . ?
C12 C13 H13 120.673 . . ?
C8 C13 H13 118.747 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 N1 1.7490(2) . ?
F1 C11 1.3547(2) . ?
N1 C1 1.3064(2) . ?
N2 C1 1.3533(2) . ?
N2 C8 1.4207(2) . ?
N2 H2N 1.0142 . ?
C1 C2 1.4894(2) . ?
C2 C7 1.3984(2) . ?
C2 C3 1.4003(2) . ?
C3 C4 1.3955(2) . ?
C3 H3 1.0812 . ?
C4 C5 1.3980(2) . ?
C4 H4 1.0956 . ?
C5 C6 1.3954(2) . ?
C5 H5 1.0848 . ?
C6 C7 1.3953(2) . ?
C6 H6 1.0780 . ?
C7 H7 1.0796 . ?
C8 C9 1.3987(2) . ?
C8 C13 1.3974(2) . ?
C9 C10 1.3963(2) . ?
C9 H9 1.0771 . ?
C10 C11 1.3876(2) . ?
C10 H10 1.0814 . ?
C11 C12 1.3857(2) . ?
C12 C13 1.3931(2) . ?
C12 H12 1.0807 . ?
C13 H13 1.0690 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 N1 Cl1 -0.05(3) . . . . ?
C2 C1 N1 Cl1 -178.31(3) . . . . ?
C8 N2 C1 N1 -176.98(2) . . . . ?
C8 N2 C1 C2 1.16(3) . . . . ?
N1 C1 C2 C7 -58.68(2) . . . . ?
N2 C1 C2 C7 122.94(2) . . . . ?
C3 C2 C1 N1 118.40(3) . . . . ?
N2 C1 C2 C3 -59.97(3) . . . . ?
C7 C2 C3 C4 0.84(3) . . . . ?
C1 C2 C3 C4 -176.20(2) . . . . ?
C2 C3 C4 C5 0.17(3) . . . . ?
C3 C4 C5 C6 -1.02(3) . . . . ?
C4 C5 C6 C7 0.86(3) . . . . ?
C5 C6 C7 C2 0.14(3) . . . . ?
C3 C2 C7 C6 -0.99(3) . . . . ?
C1 C2 C7 C6 176.09(2) . . . . ?
C1 N2 C8 C9 -46.08(3) . . . . ?
C1 N2 C8 C13 137.39(2) . . . . ?
C13 C8 C9 C10 0.52(3) . . . . ?
N2 C8 C9 C10 -175.91(2) . . . . ?
C8 C9 C10 C11 1.94(3) . . . . ?
C9 C10 C11 F1 176.31(2) . . . . ?
C9 C10 C11 C12 -2.86(3) . . . . ?
F1 C11 C12 C13 -177.95(2) . . . . ?
C10 C11 C12 C13 1.22(3) . . . . ?
C11 C12 C13 C8 1.34(3) . . . . ?
C9 C8 C13 C12 -2.19(3) . . . . ?
N2 C8 C13 C12 174.45(2) . . . . ?
