#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/18/8101855.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_8101855
loop_
_publ_author_name
'Amani, A.'
'Rezanejade Bardajee, G.'
'Jafarpour, F.'
'Razaghi, M. O.'
'Yousefi Behzadi,  M.'
'Haeri, A.'
_publ_section_title
;
 Crystal structure of 2,2-diphenyl-4-dimethyl-aminopentanenitrile,
 C₁₉H₂₂N₂
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              549
_journal_page_last               550
_journal_volume                  220
_journal_year                    2005
_chemical_formula_structural     'C19 H22 N2'
_chemical_formula_sum            'C19 H22 N2'
_chemical_formula_weight         278.39
_chemical_name_systematic        2,2-diphenyl-4-dimethylaminopentanenitrile
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.599(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6358(13)
_cell_length_b                   15.162(2)
_cell_length_c                   12.807(2)
_cell_measurement_reflns_used    898
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_cell_volume                     1607.0(4)
_computing_cell_refinement       'SAINTPlus (Bruker, 1998a)'
_computing_data_collection       'SMART (Bruker, 1998b)'
_computing_data_reduction        'SAINTPlus (Bruker, 1998a)'
_computing_molecular_graphics    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_publication_material  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_structure_refinement  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_structure_solution    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       phi/omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7566
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         2.69
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1998a)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2322
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0582P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0880
_reflns_number_gt                2073
_reflns_number_total             2322
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            1267-1634.cff
_cod_data_source_block           22dp4dmapn_aa
_cod_depositor_comments
;
 Correcting the _chemical_formula_sum and _chemical_formula_structural data
 item values by changing them from 'C18 H22 N2' to 'C19 H22 N2' after
 consulting the original publication.

 Antanas Vaitkus,
 2017-09-11

The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        1607.1(4)
_cod_original_sg_symbol_H-M      C1c1
_cod_original_formula_sum        'C18 H22 N2'
_cod_database_code               8101855
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8505(2) 0.18773(14) 0.38662(16) 0.0320(4) Uani 1 4 a d . . .
N2 N 0.6674(3) 0.37956(13) 0.29669(17) 0.0310(4) Uani 1 4 a d . . .
C1 C 0.6350(3) 0.44627(16) 0.1095(2) 0.0365(6) Uani 1 4 a d . . .
H1A H 0.6016 0.5007 0.1346 0.055 Uiso 1 4 a calc R . .
H1B H 0.5759 0.4373 0.0345 0.055 Uiso 1 4 a calc R . .
H1C H 0.7485 0.4487 0.1162 0.055 Uiso 1 4 a calc R . .
C2 C 0.6015(3) 0.36986(15) 0.17814(19) 0.0276(4) Uani 1 4 a d . . .
H2A H 0.4838 0.3664 0.1631 0.033 Uiso 1 4 a calc R . .
C3 C 0.8352(3) 0.40912(19) 0.3316(2) 0.0420(6) Uani 1 4 a d . . .
H3A H 0.8705 0.4138 0.4096 0.063 Uiso 1 4 a calc R . .
H3B H 0.8437 0.4656 0.2999 0.063 Uiso 1 4 a calc R . .
H3C H 0.9019 0.3673 0.3083 0.063 Uiso 1 4 a calc R . .
C4 C 0.5658(4) 0.43573(19) 0.3429(3) 0.0467(7) Uani 1 4 a d . . .
H4A H 0.6130 0.4403 0.4203 0.070 Uiso 1 4 a calc R . .
H4B H 0.4599 0.4103 0.3280 0.070 Uiso 1 4 a calc R . .
H4C H 0.5580 0.4934 0.3108 0.070 Uiso 1 4 a calc R . .
C5 C 0.6544(3) 0.28357(14) 0.13821(17) 0.0239(4) Uani 1 4 a d . . .
H5A H 0.7689 0.2873 0.1448 0.029 Uiso 1 4 a calc R . .
H5B H 0.5977 0.2768 0.0615 0.029 Uiso 1 4 a calc R . .
C6 C 0.6242(2) 0.20000(13) 0.19976(16) 0.0202(4) Uani 1 4 a d . . .
C7 C 0.7481(3) 0.19663(14) 0.30773(17) 0.0238(4) Uani 1 4 a d . . .
C8 C 0.4528(2) 0.20065(13) 0.21337(17) 0.0215(4) Uani 1 4 a d . . .
C9 C 0.4238(3) 0.20023(16) 0.31468(19) 0.0295(5) Uani 1 4 a d . . .
H9A H 0.5099 0.2019 0.3779 0.035 Uiso 1 4 a calc R . .
C10 C 0.2648(3) 0.19729(18) 0.3216(2) 0.0367(6) Uani 1 4 a d . . .
H10A H 0.2459 0.1963 0.3895 0.044 Uiso 1 4 a calc R . .
C11 C 0.1362(3) 0.19588(16) 0.2283(2) 0.0354(6) Uani 1 4 a d . . .
H11A H 0.0309 0.1935 0.2333 0.043 Uiso 1 4 a calc R . .
C12 C 0.1643(3) 0.19798(16) 0.1273(2) 0.0324(5) Uani 1 4 a d . . .
H12A H 0.0778 0.1981 0.0643 0.039 Uiso 1 4 a calc R . .
C13 C 0.3221(3) 0.19986(14) 0.11967(18) 0.0258(4) Uani 1 4 a d . . .
H13A H 0.3403 0.2006 0.0515 0.031 Uiso 1 4 a calc R . .
C14 C 0.6494(2) 0.11326(14) 0.14290(17) 0.0232(4) Uani 1 4 a d . . .
C15 C 0.6112(3) 0.03373(15) 0.1848(2) 0.0317(5) Uani 1 4 a d . . .
H15A H 0.5707 0.0344 0.2447 0.038 Uiso 1 4 a calc R . .
C16 C 0.6328(3) -0.04655(17) 0.1378(3) 0.0393(6) Uani 1 4 a d . . .
H16A H 0.6073 -0.0991 0.1665 0.047 Uiso 1 4 a calc R . .
C17 C 0.6927(3) -0.04759(19) 0.0479(2) 0.0402(6) Uani 1 4 a d . . .
H17A H 0.7066 -0.1009 0.0159 0.048 Uiso 1 4 a calc R . .
C18 C 0.7310(3) 0.03009(19) 0.0066(2) 0.0390(6) Uani 1 4 a d . . .
H18A H 0.7716 0.0291 -0.0533 0.047 Uiso 1 4 a calc R . .
C19 C 0.7099(3) 0.11095(17) 0.05339(18) 0.0310(5) Uani 1 4 a d . . .
H19A H 0.7365 0.1632 0.0245 0.037 Uiso 1 4 a calc R . .
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 0.0000 '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 0.0000 '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
C3 N2 C4 110.8(2) . . ?
C3 N2 C2 113.9(2) . . ?
C4 N2 C2 112.1(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C2 C5 111.62(18) . . ?
N2 C2 C1 115.9(2) . . ?
C5 C2 C1 109.45(19) . . ?
N2 C2 H2A 106.4 . . ?
C5 C2 H2A 106.4 . . ?
C1 C2 H2A 106.4 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 C6 114.88(16) . . ?
C2 C5 H5A 108.5 . . ?
C6 C5 H5A 108.5 . . ?
C2 C5 H5B 108.5 . . ?
C6 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
N1 C7 C6 173.4(2) . . ?
C7 C6 C8 110.77(16) . . ?
C7 C6 C14 104.32(17) . . ?
C8 C6 C14 109.13(17) . . ?
C7 C6 C5 108.61(17) . . ?
C8 C6 C5 111.02(17) . . ?
C14 C6 C5 112.81(16) . . ?
C13 C8 C9 119.11(19) . . ?
C13 C8 C6 118.12(18) . . ?
C9 C8 C6 122.76(19) . . ?
C8 C9 C10 120.0(2) . . ?
C8 C9 H9A 120.0 . . ?
C10 C9 H9A 120.0 . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10A 119.8 . . ?
C9 C10 H10A 119.8 . . ?
C10 C11 C12 119.7(2) . . ?
C10 C11 H11A 120.1 . . ?
C12 C11 H11A 120.1 . . ?
C11 C12 C13 120.2(2) . . ?
C11 C12 H12A 119.9 . . ?
C13 C12 H12A 119.9 . . ?
C8 C13 C12 120.5(2) . . ?
C8 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
C19 C14 C15 118.7(2) . . ?
C19 C14 C6 123.1(2) . . ?
C15 C14 C6 118.17(18) . . ?
C16 C15 C14 120.9(2) . . ?
C16 C15 H15A 119.6 . . ?
C14 C15 H15A 119.6 . . ?
C17 C16 C15 119.6(3) . . ?
C17 C16 H16A 120.2 . . ?
C15 C16 H16A 120.2 . . ?
C18 C17 C16 119.9(3) . . ?
C18 C17 H17A 120.1 . . ?
C16 C17 H17A 120.1 . . ?
C17 C18 C19 120.8(2) . . ?
C17 C18 H18A 119.6 . . ?
C19 C18 H18A 119.6 . . ?
C14 C19 C18 120.1(2) . . ?
C14 C19 H19A 120.0 . . ?
C18 C19 H19A 120.0 . . ?
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
N1 C7 1.145(3) . ?
N2 C3 1.460(3) . ?
N2 C4 1.464(3) . ?
N2 C2 1.469(3) . ?
C1 C2 1.532(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C5 1.522(3) . ?
C2 H2A 0.9800 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.553(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C7 C6 1.488(3) . ?
C6 C8 1.539(3) . ?
C6 C14 1.549(3) . ?
C8 C13 1.393(3) . ?
C8 C9 1.390(3) . ?
C9 C10 1.402(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.380(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.384(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.394(3) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 C19 1.390(3) . ?
C14 C15 1.397(3) . ?
C15 C16 1.394(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.391(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.370(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.399(4) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
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
C3 N2 C2 C5 79.8(2) . . . . ?
C4 N2 C2 C5 -153.4(2) . . . . ?
C3 N2 C2 C1 -46.4(3) . . . . ?
C4 N2 C2 C1 80.4(3) . . . . ?
N2 C2 C5 C6 51.4(2) . . . . ?
C1 C2 C5 C6 -178.93(19) . . . . ?
N1 C7 C6 C8 133(2) . . . . ?
N1 C7 C6 C14 16(2) . . . . ?
N1 C7 C6 C5 -105(2) . . . . ?
C2 C5 C6 C7 -75.8(2) . . . . ?
C2 C5 C6 C8 46.3(2) . . . . ?
C2 C5 C6 C14 169.12(18) . . . . ?
C7 C6 C8 C13 -177.28(18) . . . . ?
C14 C6 C8 C13 -63.0(2) . . . . ?
C5 C6 C8 C13 62.0(2) . . . . ?
C7 C6 C8 C9 1.4(3) . . . . ?
C14 C6 C8 C9 115.7(2) . . . . ?
C5 C6 C8 C9 -119.3(2) . . . . ?
C13 C8 C9 C10 1.2(4) . . . . ?
C6 C8 C9 C10 -177.4(2) . . . . ?
C8 C9 C10 C11 -0.8(4) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C10 C11 C12 C13 1.2(4) . . . . ?
C9 C8 C13 C12 -0.5(3) . . . . ?
C6 C8 C13 C12 178.26(19) . . . . ?
C11 C12 C13 C8 -0.7(4) . . . . ?
C7 C6 C14 C19 -111.0(2) . . . . ?
C8 C6 C14 C19 130.6(2) . . . . ?
C5 C6 C14 C19 6.7(3) . . . . ?
C7 C6 C14 C15 68.2(2) . . . . ?
C8 C6 C14 C15 -50.2(3) . . . . ?
C5 C6 C14 C15 -174.08(19) . . . . ?
C19 C14 C15 C16 -0.1(3) . . . . ?
C6 C14 C15 C16 -179.4(2) . . . . ?
C14 C15 C16 C17 -0.2(4) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C16 C17 C18 C19 -0.4(4) . . . . ?
C15 C14 C19 C18 0.2(3) . . . . ?
C6 C14 C19 C18 179.4(2) . . . . ?
C17 C18 C19 C14 0.0(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 29065
