#------------------------------------------------------------------------------
#$Date: 2022-03-10 11:51:05 +0200 (Thu, 10 Mar 2022) $
#$Revision: 273599 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/47/8104722.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_8104722
loop_
_publ_author_name
'Ning, Zhi Wei'
'Gan, Lin Ling'
'Zhou, Shu Jing'
'Tian, Jie'
'Du, Yu Hui'
'Zhang, Hui Zhen'
_publ_section_title
;
 Crystal structure of N 1,N
 2-bis(2-fluorobenzyl)benzene-1,2-diamine,C20H18F2N2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              819
_journal_page_last               820
_journal_paper_doi               10.1515/ncrs-2021-0094
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C20 H18 F2 N2'
_chemical_formula_sum            'C20 H18 F2 N2'
_chemical_formula_weight         324.36
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_cell_angle_alpha                90
_cell_angle_beta                 104.109(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4233(11)
_cell_length_b                   7.3805(7)
_cell_length_c                   18.9531(16)
_cell_measurement_reflns_used    1720
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.663
_cell_measurement_theta_min      2.761
_cell_volume                     1685.4(3)
_computing_cell_refinement       'SAINT V6.36A (?, 2016)'
_computing_data_reduction        'SAINT V6.36A (?, 2016)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1036
_diffrn_reflns_av_unetI/netI     0.1004
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8005
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.984
_diffrn_reflns_theta_max         24.984
_diffrn_reflns_theta_min         2.974
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      .
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0070(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.946
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0464
_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/[σ²(Fo²)+(0.0000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1201
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1455
_reflns_number_total             2957
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0094_suppl.cif
_cod_data_source_block           180913c
_cod_database_code               8104722
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(H5)=Sof(F1A)=1-FVAR(1)
 Sof(H1)=Sof(F1)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C14(H14A,H14B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C17(H17), C18(H18), C19(H19), C20(H20)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C1 C 0.1777(3) 0.4570(5) 0.55252(15) 0.0748(8) Uani 1 1 d . . . . .
H1 H 0.1486 0.5423 0.5788 0.090 Uiso 0.579(5) 1 calc R . P A 1
C2 C 0.1201(3) 0.2998(5) 0.53252(16) 0.0874(10) Uani 1 1 d . . . . .
H2 H 0.0527 0.2806 0.5445 0.105 Uiso 1 1 calc R . . . .
C3 C 0.1624(3) 0.1705(5) 0.49465(15) 0.0862(10) Uani 1 1 d . . . . .
H3 H 0.1244 0.0624 0.4813 0.103 Uiso 1 1 calc R . . . .
C4 C 0.2623(3) 0.2024(4) 0.47644(14) 0.0792(9) Uani 1 1 d . . . . .
H4 H 0.2912 0.1173 0.4499 0.095 Uiso 1 1 calc R . . . .
C5 C 0.3174(3) 0.3599(5) 0.49794(14) 0.0701(8) Uani 1 1 d . . . . .
H5 H 0.3855 0.3780 0.4869 0.084 Uiso 0.421(5) 1 calc R . P A 2
C6 C 0.2772(2) 0.4947(4) 0.53542(12) 0.0591(7) Uani 1 1 d . . . . .
C7 C 0.3394(2) 0.6679(4) 0.55588(12) 0.0676(8) Uani 1 1 d . . . . .
H7A H 0.3716 0.7063 0.5166 0.081 Uiso 1 1 calc R . . . .
H7B H 0.2886 0.7616 0.5634 0.081 Uiso 1 1 calc R . . . .
C8 C 0.5056(2) 0.7805(4) 0.64599(12) 0.0508(6) Uani 1 1 d . . . . .
C9 C 0.4969(2) 0.9535(4) 0.61579(13) 0.0659(8) Uani 1 1 d . . . . .
H9 H 0.4365 0.9826 0.5778 0.079 Uiso 1 1 calc R . . . .
C10 C 0.5774(3) 1.0823(4) 0.64200(17) 0.0771(9) Uani 1 1 d . . . . .
H10 H 0.5709 1.1975 0.6215 0.093 Uiso 1 1 calc R . . . .
C11 C 0.6665(3) 1.0414(4) 0.69791(18) 0.0805(9) Uani 1 1 d . . . . .
H11 H 0.7205 1.1287 0.7152 0.097 Uiso 1 1 calc R . . . .
C12 C 0.6766(2) 0.8709(4) 0.72870(14) 0.0660(7) Uani 1 1 d . . . . .
H12 H 0.7375 0.8445 0.7667 0.079 Uiso 1 1 calc R . . . .
C13 C 0.5976(2) 0.7386(3) 0.70390(12) 0.0510(6) Uani 1 1 d . . . . .
C14 C 0.7040(2) 0.5046(3) 0.78625(12) 0.0603(7) Uani 1 1 d . . . . .
H14A H 0.6874 0.3922 0.8079 0.072 Uiso 1 1 calc R . . . .
H14B H 0.7201 0.5955 0.8244 0.072 Uiso 1 1 calc R . . . .
C15 C 0.8058(2) 0.4773(3) 0.75771(11) 0.0489(6) Uani 1 1 d . . . . .
C16 C 0.9073(2) 0.4380(4) 0.80387(12) 0.0613(7) Uani 1 1 d . . . . .
C17 C 1.0027(2) 0.4067(4) 0.78206(15) 0.0778(9) Uani 1 1 d . . . . .
H17 H 1.0687 0.3803 0.8159 0.093 Uiso 1 1 calc R . . . .
C18 C 0.9990(3) 0.4149(4) 0.70898(16) 0.0838(9) Uani 1 1 d . . . . .
H18 H 1.0627 0.3954 0.6925 0.101 Uiso 1 1 calc R . . . .
C19 C 0.9000(3) 0.4524(4) 0.66086(14) 0.0755(9) Uani 1 1 d . . . . .
H19 H 0.8967 0.4566 0.6113 0.091 Uiso 1 1 calc R . . . .
C20 C 0.8048(2) 0.4841(3) 0.68435(13) 0.0609(7) Uani 1 1 d . . . . .
H20 H 0.7389 0.5104 0.6504 0.073 Uiso 1 1 calc R . . . .
F1 F 0.4115(3) 0.3927(5) 0.48346(14) 0.0980(14) Uani 0.579(5) 1 d . . P A 1
F1A F 0.1450(4) 0.5726(6) 0.5906(3) 0.113(2) Uani 0.421(5) 1 d . . P A 2
F2 F 0.91046(14) 0.4293(2) 0.87692(7) 0.0986(6) Uani 1 1 d . . . . .
N1 N 0.42681(18) 0.6445(4) 0.62191(10) 0.0590(6) Uani 1 1 d . . . . .
H1A H 0.454(2) 0.539(4) 0.6348(14) 0.079(10) Uiso 1 1 d . . . . .
N2 N 0.6066(2) 0.5608(3) 0.73116(11) 0.0560(6) Uani 1 1 d . . . . .
H2A H 0.545(3) 0.527(4) 0.7344(15) 0.092(11) Uiso 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'
F F 0.0171 0.0103 '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'
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
C2 C1 H1 118.5 . .
C2 C1 C6 123.0(3) . .
C6 C1 H1 118.5 . .
F1A C1 C2 121.2(4) . .
F1A C1 C6 115.7(4) . .
C1 C2 H2 120.2 . .
C1 C2 C3 119.5(3) . .
C3 C2 H2 120.2 . .
C2 C3 H3 120.3 . .
C2 C3 C4 119.5(3) . .
C4 C3 H3 120.3 . .
C3 C4 H4 120.5 . .
C5 C4 C3 119.1(3) . .
C5 C4 H4 120.5 . .
C4 C5 H5 118.3 . .
C4 C5 C6 123.4(3) . .
C6 C5 H5 118.3 . .
F1 C5 C4 120.9(3) . .
F1 C5 C6 115.7(3) . .
C1 C6 C5 115.5(3) . .
C1 C6 C7 123.2(3) . .
C5 C6 C7 121.3(3) . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 108.1 . .
N1 C7 C6 110.6(2) . .
N1 C7 H7A 109.5 . .
N1 C7 H7B 109.5 . .
C9 C8 C13 119.2(2) . .
C9 C8 N1 123.1(2) . .
N1 C8 C13 117.8(2) . .
C8 C9 H9 119.8 . .
C10 C9 C8 120.4(3) . .
C10 C9 H9 119.8 . .
C9 C10 H10 119.8 . .
C11 C10 C9 120.4(3) . .
C11 C10 H10 119.8 . .
C10 C11 H11 119.9 . .
C10 C11 C12 120.1(3) . .
C12 C11 H11 119.9 . .
C11 C12 H12 119.5 . .
C11 C12 C13 121.1(3) . .
C13 C12 H12 119.5 . .
C12 C13 C8 118.8(2) . .
C12 C13 N2 123.2(2) . .
N2 C13 C8 117.9(2) . .
H14A C14 H14B 107.7 . .
C15 C14 H14A 108.8 . .
C15 C14 H14B 108.8 . .
N2 C14 H14A 108.8 . .
N2 C14 H14B 108.8 . .
N2 C14 C15 113.92(19) . .
C16 C15 C14 121.2(2) . .
C16 C15 C20 115.2(2) . .
C20 C15 C14 123.5(2) . .
C17 C16 C15 124.7(2) . .
C17 C16 F2 118.8(2) . .
F2 C16 C15 116.4(2) . .
C16 C17 H17 120.7 . .
C16 C17 C18 118.6(3) . .
C18 C17 H17 120.7 . .
C17 C18 H18 120.5 . .
C19 C18 C17 118.9(3) . .
C19 C18 H18 120.5 . .
C18 C19 H19 119.3 . .
C18 C19 C20 121.3(3) . .
C20 C19 H19 119.3 . .
C15 C20 H20 119.4 . .
C19 C20 C15 121.2(2) . .
C19 C20 H20 119.4 . .
C7 N1 H1A 120.8(19) . .
C8 N1 C7 120.8(2) . .
C8 N1 H1A 111(2) . .
C13 N2 C14 120.6(2) . .
C13 N2 H2A 109(2) . .
C14 N2 H2A 119(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 H1 0.9300 .
C1 C2 1.368(4) .
C1 C6 1.381(4) .
C1 F1A 1.248(4) .
C2 H2 0.9300 .
C2 C3 1.374(4) .
C3 H3 0.9300 .
C3 C4 1.387(4) .
C4 H4 0.9300 .
C4 C5 1.360(4) .
C5 H5 0.9300 .
C5 C6 1.384(4) .
C5 F1 1.288(4) .
C6 C7 1.495(4) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C7 N1 1.454(3) .
C8 C9 1.393(3) .
C8 C13 1.412(3) .
C8 N1 1.399(3) .
C9 H9 0.9300 .
C9 C10 1.381(4) .
C10 H10 0.9300 .
C10 C11 1.367(4) .
C11 H11 0.9300 .
C11 C12 1.380(4) .
C12 H12 0.9300 .
C12 C13 1.383(3) .
C13 N2 1.405(3) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C14 C15 1.505(3) .
C14 N2 1.453(3) .
C15 C16 1.379(3) .
C15 C20 1.388(3) .
C16 C17 1.366(4) .
C16 F2 1.377(3) .
C17 H17 0.9300 .
C17 C18 1.376(3) .
C18 H18 0.9300 .
C18 C19 1.369(4) .
C19 H19 0.9300 .
C19 C20 1.381(4) .
C20 H20 0.9300 .
N1 H1A 0.86(3) .
N2 H2A 0.82(3) .
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
C1 C2 C3 C4 -0.9(4) . . . .
C1 C6 C7 N1 97.7(3) . . . .
C2 C1 C6 C5 -1.7(4) . . . .
C2 C1 C6 C7 178.7(2) . . . .
C2 C3 C4 C5 1.4(4) . . . .
C3 C4 C5 C6 -2.2(4) . . . .
C3 C4 C5 F1 178.5(3) . . . .
C4 C5 C6 C1 2.3(4) . . . .
C4 C5 C6 C7 -178.1(2) . . . .
C5 C6 C7 N1 -81.8(3) . . . .
C6 C1 C2 C3 1.1(4) . . . .
C6 C7 N1 C8 171.1(2) . . . .
C8 C9 C10 C11 0.0(4) . . . .
C8 C13 N2 C14 174.5(2) . . . .
C9 C8 C13 C12 -0.3(3) . . . .
C9 C8 C13 N2 -177.3(2) . . . .
C9 C8 N1 C7 9.8(4) . . . .
C9 C10 C11 C12 -0.1(4) . . . .
C10 C11 C12 C13 0.0(4) . . . .
C11 C12 C13 C8 0.2(4) . . . .
C11 C12 C13 N2 177.0(2) . . . .
C12 C13 N2 C14 -2.3(4) . . . .
C13 C8 C9 C10 0.3(4) . . . .
C13 C8 N1 C7 -170.6(2) . . . .
C14 C15 C16 C17 178.2(3) . . . .
C14 C15 C16 F2 -1.4(4) . . . .
C14 C15 C20 C19 -177.9(3) . . . .
C15 C14 N2 C13 -74.2(3) . . . .
C15 C16 C17 C18 0.3(5) . . . .
C16 C15 C20 C19 0.2(4) . . . .
C16 C17 C18 C19 -0.6(4) . . . .
C17 C18 C19 C20 0.8(5) . . . .
C18 C19 C20 C15 -0.6(4) . . . .
C20 C15 C16 C17 0.0(4) . . . .
C20 C15 C16 F2 -179.6(2) . . . .
F1 C5 C6 C1 -178.3(3) . . . .
F1 C5 C6 C7 1.2(4) . . . .
F1A C1 C2 C3 -175.8(4) . . . .
F1A C1 C6 C5 175.3(3) . . . .
F1A C1 C6 C7 -4.3(5) . . . .
F2 C16 C17 C18 179.8(2) . . . .
N1 C8 C9 C10 179.9(2) . . . .
N1 C8 C13 C12 -180.0(2) . . . .
N1 C8 C13 N2 3.0(3) . . . .
N2 C14 C15 C16 174.8(2) . . . .
N2 C14 C15 C20 -7.2(3) . . . .
