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#$Date: 2022-05-19 11:55:07 +0300 (Thu, 19 May 2022) $
#$Revision: 275543 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/53/8105302.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_8105302
loop_
_publ_author_name
'Mo, Shuang-Ming'
'Shi, Da-Bin'
_publ_section_title
;
 Crystal structure of
 4′-amino-3′,5′-diisopropyl-(1,1′-biphenyl)-4-carbonitrile,
 C19H22N2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              837
_journal_page_last               839
_journal_paper_doi               10.1515/ncrs-2020-0038
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C19 H22 N2'
_chemical_formula_sum            'C19 H22 N2'
_chemical_formula_weight         278.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                87.278(5)
_cell_angle_beta                 71.092(6)
_cell_angle_gamma                66.190(6)
_cell_formula_units_Z            2
_cell_length_a                   8.1330(5)
_cell_length_b                   9.3474(5)
_cell_length_c                   12.1520(8)
_cell_measurement_reflns_used    3041
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.460
_cell_measurement_theta_min      3.863
_cell_volume                     795.88(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXL-2018/1 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.6525
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4642
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.460
_diffrn_reflns_theta_min         3.863
_exptl_absorpt_coefficient_mu    0.520
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59800
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.1137
_exptl_transmission_factor_min   0.0909
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3041
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0498
_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)+(0.0909P)²+0.1137P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1360
_refine_ls_wR_factor_ref         0.1415
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2743
_reflns_number_total             3041
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0038_suppl.cif
_cod_data_source_block           49
_cod_original_cell_volume        795.88(9)
_cod_database_code               8105302
_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.
;
_shelx_estimated_absorpt_t_min   0.903
_shelx_estimated_absorpt_t_max   0.903
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 1.36460(18) -0.09322(15) 0.10047(11) 0.0297(3) Uani 1 1 d . . . . .
C2 C 1.27955(17) -0.00035(15) 0.21130(10) 0.0258(3) Uani 1 1 d . . . . .
C3 C 1.29136(18) -0.07450(14) 0.31218(11) 0.0274(3) Uani 1 1 d . . . . .
H3 H 1.359314 -0.182683 0.307359 0.033 Uiso 1 1 calc R U . . .
C4 C 1.20179(17) 0.01314(14) 0.41956(10) 0.0270(3) Uani 1 1 d . . . . .
H4 H 1.211578 -0.037284 0.486471 0.032 Uiso 1 1 calc R U . . .
C5 C 1.09649(16) 0.17618(13) 0.43025(10) 0.0231(3) Uani 1 1 d . . . . .
C6 C 1.08856(17) 0.24886(14) 0.32721(10) 0.0252(3) Uani 1 1 d . . . . .
H6 H 1.021490 0.357120 0.331641 0.030 Uiso 1 1 calc R U . . .
C7 C 1.17870(18) 0.16237(14) 0.21921(10) 0.0269(3) Uani 1 1 d . . . . .
H7 H 1.172172 0.212551 0.151828 0.032 Uiso 1 1 calc R U . . .
C8 C 0.99380(17) 0.26620(13) 0.54654(10) 0.0232(3) Uani 1 1 d . . . . .
C9 C 1.05474(17) 0.21262(13) 0.64188(10) 0.0243(3) Uani 1 1 d . . . . .
H9 H 1.165412 0.121505 0.629984 0.029 Uiso 1 1 calc R U . . .
C10 C 0.95688(17) 0.28982(14) 0.75331(10) 0.0244(3) Uani 1 1 d . . . . .
C11 C 0.78960(17) 0.42900(14) 0.77139(10) 0.0246(3) Uani 1 1 d . . . . .
C12 C 0.72247(17) 0.48523(13) 0.67690(10) 0.0234(3) Uani 1 1 d . . . . .
C13 C 0.82646(17) 0.40341(13) 0.56731(10) 0.0234(3) Uani 1 1 d . . . . .
H13 H 0.783438 0.441093 0.505085 0.028 Uiso 1 1 calc R U . . .
C14 C 1.02937(19) 0.22927(15) 0.85452(11) 0.0292(3) Uani 1 1 d . . . . .
H14 H 0.917841 0.250589 0.924825 0.035 Uiso 1 1 calc R U . . .
C15 C 1.1394(2) 0.31898(18) 0.87570(13) 0.0414(4) Uani 1 1 d . . . . .
H15A H 1.252991 0.296521 0.809574 0.062 Uiso 1 1 calc R U . . .
H15B H 1.173300 0.286922 0.944409 0.062 Uiso 1 1 calc R U . . .
H15C H 1.060877 0.429731 0.886407 0.062 Uiso 1 1 calc R U . . .
C16 C 1.1522(2) 0.05297(17) 0.83884(13) 0.0407(4) Uani 1 1 d . . . . .
H16A H 1.087289 -0.002094 0.818407 0.061 Uiso 1 1 calc R U . . .
H16B H 1.174905 0.019680 0.910513 0.061 Uiso 1 1 calc R U . . .
H16C H 1.271657 0.030370 0.777745 0.061 Uiso 1 1 calc R U . . .
C17 C 0.53474(17) 0.62867(14) 0.69937(11) 0.0280(3) Uani 1 1 d . . . . .
H17 H 0.533137 0.706564 0.751376 0.034 Uiso 1 1 calc R U . . .
C18 C 0.5060(2) 0.70635(15) 0.58957(12) 0.0349(3) Uani 1 1 d . . . . .
H18A H 0.615222 0.726585 0.546919 0.052 Uiso 1 1 calc R U . . .
H18B H 0.394311 0.803583 0.611486 0.052 Uiso 1 1 calc R U . . .
H18C H 0.490368 0.637687 0.541328 0.052 Uiso 1 1 calc R U . . .
C19 C 0.36701(19) 0.58555(17) 0.76319(14) 0.0406(4) Uani 1 1 d . . . . .
H19A H 0.355430 0.519023 0.710977 0.061 Uiso 1 1 calc R U . . .
H19B H 0.251529 0.679567 0.789031 0.061 Uiso 1 1 calc R U . . .
H19C H 0.389093 0.531089 0.829489 0.061 Uiso 1 1 calc R U . . .
N1 N 1.42881(18) -0.16902(14) 0.01327(10) 0.0393(3) Uani 1 1 d . . . . .
N2 N 0.69287(17) 0.50982(13) 0.88095(9) 0.0359(3) Uani 1 1 d . . . . .
H2A H 0.734384 0.475483 0.937947 0.043 Uiso 1 1 calc R U . . .
H2B H 0.590994 0.594594 0.892335 0.043 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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
C10 C9 C8 122.63(11) . .
C10 C9 H9 118.7 . .
C8 C9 H9 118.7 . .
C11 N2 H2A 120.0 . .
C11 N2 H2B 120.0 . .
H2A N2 H2B 120.0 . .
C13 C12 C11 118.70(10) . .
C13 C12 C17 121.85(10) . .
C11 C12 C17 119.39(11) . .
C9 C8 C13 117.33(11) . .
C9 C8 C5 121.03(10) . .
C13 C8 C5 121.55(11) . .
N2 C11 C10 119.70(11) . .
N2 C11 C12 120.32(11) . .
C10 C11 C12 119.97(11) . .
C12 C13 C8 122.57(11) . .
C12 C13 H13 118.7 . .
C8 C13 H13 118.7 . .
N1 C1 C2 178.12(14) . .
C4 C5 C6 117.60(11) . .
C4 C5 C8 120.67(11) . .
C6 C5 C8 121.71(10) . .
C6 C7 C2 120.02(11) . .
C6 C7 H7 120.0 . .
C2 C7 H7 120.0 . .
C9 C10 C11 118.78(11) . .
C9 C10 C14 121.11(11) . .
C11 C10 C14 120.09(11) . .
C4 C3 C2 119.75(11) . .
C4 C3 H3 120.1 . .
C2 C3 H3 120.1 . .
C7 C6 C5 121.17(11) . .
C7 C6 H6 119.4 . .
C5 C6 H6 119.4 . .
C3 C4 C5 121.68(11) . .
C3 C4 H4 119.2 . .
C5 C4 H4 119.2 . .
C10 C14 C16 113.82(10) . .
C10 C14 C15 110.41(11) . .
C16 C14 C15 109.86(12) . .
C10 C14 H14 107.5 . .
C16 C14 H14 107.5 . .
C15 C14 H14 107.5 . .
C12 C17 C18 114.28(10) . .
C12 C17 C19 110.15(10) . .
C18 C17 C19 109.61(11) . .
C12 C17 H17 107.5 . .
C18 C17 H17 107.5 . .
C19 C17 H17 107.5 . .
C3 C2 C7 119.75(11) . .
C3 C2 C1 119.45(11) . .
C7 C2 C1 120.74(11) . .
C17 C19 H19A 109.5 . .
C17 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C17 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C14 C16 H16A 109.5 . .
C14 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C14 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C9 C10 1.3851(16) .
C9 C8 1.3983(16) .
C9 H9 0.9300 .
N2 C11 1.3781(15) .
N2 H2A 0.8600 .
N2 H2B 0.8600 .
C12 C13 1.3850(16) .
C12 C11 1.4178(17) .
C12 C17 1.5216(16) .
C8 C13 1.3998(16) .
C8 C5 1.4776(16) .
C11 C10 1.4128(17) .
C13 H13 0.9300 .
C1 N1 1.1452(17) .
C1 C2 1.4382(16) .
C5 C4 1.4020(17) .
C5 C6 1.4035(16) .
C7 C6 1.3828(16) .
C7 C2 1.3967(17) .
C7 H7 0.9300 .
C10 C14 1.5215(16) .
C3 C4 1.3814(17) .
C3 C2 1.3908(18) .
C3 H3 0.9300 .
C6 H6 0.9300 .
C4 H4 0.9300 .
C14 C16 1.5256(18) .
C14 C15 1.5316(19) .
C14 H14 0.9800 .
C17 C18 1.5282(18) .
C17 C19 1.5341(19) .
C17 H17 0.9800 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2B N1 0.86 2.34 3.0372(16) 138.3 1_466 yes
N2 H2B N1 0.86 2.34 3.0372(16) 138.3 1_466 yes
N2 H2B N1 0.86 2.34 3.0372(16) 138.3 1_466 yes
