#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/83/2238390.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2238390
loop_
_publ_author_name
'Majer, Sean H.'
'Tanski, Joseph M.'
_publ_section_title
;
 (E)-Benzyl(1-phenylethylidene)amine
;
_journal_coeditor_code           LD2110
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1289
_journal_paper_doi               10.1107/S1600536813019636
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C15 H15 N'
_chemical_formula_moiety         'C15 H15 N'
_chemical_formula_sum            'C15 H15 N'
_chemical_formula_weight         209.28
_chemical_name_systematic
;
(E)-Benzyl(1-phenylethylidene)amine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 97.3080(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.4633(4)
_cell_length_b                   10.4173(8)
_cell_length_c                   20.2426(15)
_cell_measurement_reflns_used    5923
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      30.45
_cell_measurement_theta_min      2.20
_cell_volume                     1142.71(15)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), OLEX2 (Dolomanov, et al.,
2009) and Mercury
(Macrae et al., 2006)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0422
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            18404
_diffrn_reflns_theta_full        30.53
_diffrn_reflns_theta_max         30.53
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9979
_exptl_absorpt_correction_T_min  0.9778
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Bruker 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.196
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         3496
_refine_ls_number_restraints     105
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0568P)²+0.3065P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1268
_reflns_number_gt                2509
_reflns_number_total             3496
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ld2110.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2238390
_cod_database_fobs_code          2238390
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.6967(5) 0.9477(3) 0.15570(10) 0.0197(4) Uani d PDU 0.909(2) 1 A 1
C C1 0.5051(3) 0.95089(15) 0.11114(9) 0.0153(3) Uani d PDU 0.909(2) 1 A 1
C C2 0.2936(2) 1.04626(13) 0.11017(6) 0.0223(3) Uani d PDU 0.909(2) 1 A 1
H H2A 0.3278 1.1058 0.1477 0.033 Uiso calc PR 0.909(2) 1 A 1
H H2B 0.1399 0.9998 0.1139 0.033 Uiso calc PR 0.909(2) 1 A 1
H H2C 0.2769 1.0946 0.0683 0.033 Uiso calc PR 0.909(2) 1 A 1
C C9 0.7279(4) 1.04393(17) 0.20835(9) 0.0211(3) Uani d PDU 0.909(2) 1 A 1
H H9A 0.5803 1.0444 0.2321 0.025 Uiso calc PR 0.909(2) 1 A 1
H H9B 0.7430 1.1299 0.1884 0.025 Uiso calc PR 0.909(2) 1 A 1
N N1' 0.704(6) 0.952(4) 0.1458(14) 0.0197(4) Uani d PDU 0.091(2) 1 A 2
C C1' 0.724(4) 1.0191(18) 0.1996(11) 0.0153(3) Uani d PDU 0.091(2) 1 A 2
C C2' 0.582(2) 1.1406(12) 0.2104(6) 0.0223(3) Uani d PDU 0.091(2) 1 A 2
H H2'A 0.4768 1.1632 0.1691 0.033 Uiso calc PR 0.091(2) 1 A 2
H H2'B 0.6975 1.2107 0.2232 0.033 Uiso calc PR 0.091(2) 1 A 2
H H2'C 0.4782 1.1263 0.2459 0.033 Uiso calc PR 0.091(2) 1 A 2
C C9' 0.458(4) 0.972(2) 0.1105(11) 0.0211(3) Uani d PDU 0.091(2) 1 A 2
H H9'A 0.4371 1.0570 0.0889 0.025 Uiso calc PR 0.091(2) 1 A 2
H H9'B 0.3250 0.9563 0.1386 0.025 Uiso calc PR 0.091(2) 1 A 2
C C3 0.48698(19) 0.85340(10) 0.05684(5) 0.0171(2) Uani d . 1 1 . .
C C4 0.2827(2) 0.84705(11) 0.00784(6) 0.0206(2) Uani d . 1 1 A .
H H4A 0.1521 0.9071 0.0084 0.025 Uiso calc R 1 1 . .
C C5 0.2681(2) 0.75399(12) -0.04178(6) 0.0236(3) Uani d . 1 1 . .
H H5A 0.1277 0.7508 -0.0746 0.028 Uiso calc R 1 1 A .
C C6 0.4574(2) 0.66577(12) -0.04357(6) 0.0242(3) Uani d . 1 1 A .
H H6A 0.4473 0.6022 -0.0775 0.029 Uiso calc R 1 1 . .
C C7 0.6625(2) 0.67147(12) 0.00486(6) 0.0232(2) Uani d . 1 1 . .
H H7A 0.7931 0.6115 0.0039 0.028 Uiso calc R 1 1 A .
C C8 0.6775(2) 0.76402(11) 0.05436(6) 0.0205(2) Uani d . 1 1 A .
H H8A 0.8185 0.7670 0.0870 0.025 Uiso calc R 1 1 . .
C C10 0.9543(2) 1.01713(11) 0.25738(5) 0.0200(2) Uani d . 1 1 . .
C C11 1.0927(2) 0.90513(12) 0.25703(6) 0.0255(3) Uani d . 1 1 A .
H H11A 1.0448 0.8404 0.2249 0.031 Uiso calc R 1 1 . .
C C12 1.3012(2) 0.88711(13) 0.30342(6) 0.0273(3) Uani d . 1 1 . .
H H12A 1.3949 0.8104 0.3026 0.033 Uiso calc R 1 1 A .
C C13 1.3727(2) 0.98068(13) 0.35076(6) 0.0250(3) Uani d . 1 1 A .
H H13A 1.5162 0.9688 0.3819 0.030 Uiso calc R 1 1 . .
C C14 1.2336(2) 1.09130(12) 0.35225(6) 0.0247(3) Uani d . 1 1 . .
H H14A 1.2802 1.1550 0.3850 0.030 Uiso calc R 1 1 A .
C C15 1.0257(2) 1.10962(12) 0.30587(6) 0.0226(2) Uani d . 1 1 A .
H H15A 0.9313 1.1859 0.3072 0.027 Uiso calc R 1 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C9 120.1(2)
N1 C1 C3 118.00(15)
N1 C1 C2 124.87(17)
C3 C1 C2 117.12(12)
N1 C9 C10 111.31(15)
N1 C9 H9A 109.4
C10 C9 H9A 109.4
N1 C9 H9B 109.4
C10 C9 H9B 109.4
H9A C9 H9B 108.0
C1' N1' C9' 108.1(19)
N1' C1' C2' 126(2)
N1' C1' C10 125.7(16)
C2' C1' C10 106.0(11)
C1' C2' H2'A 109.5
C1' C2' H2'B 109.5
H2'A C2' H2'B 109.5
C1' C2' H2'C 109.5
H2'A C2' H2'C 109.5
H2'B C2' H2'C 109.5
N1' C9' C3 93.1(14)
N1' C9' H9'A 113.1
C3 C9' H9'A 113.1
N1' C9' H9'B 113.1
C3 C9' H9'B 113.1
H9'A C9' H9'B 110.5
C4 C3 C8 118.20(10)
C4 C3 C1 121.88(10)
C8 C3 C1 119.92(10)
C4 C3 C9' 111.3(6)
C8 C3 C9' 130.5(6)
C5 C4 C3 120.87(11)
C5 C4 H4A 119.6
C3 C4 H4A 119.6
C6 C5 C4 120.40(11)
C6 C5 H5A 119.8
C4 C5 H5A 119.8
C5 C6 C7 119.27(11)
C5 C6 H6A 120.4
C7 C6 H6A 120.4
C8 C7 C6 120.44(11)
C8 C7 H7A 119.8
C6 C7 H7A 119.8
C7 C8 C3 120.83(10)
C7 C8 H8A 119.6
C3 C8 H8A 119.6
C11 C10 C15 118.64(10)
C11 C10 C9 123.52(11)
C15 C10 C9 117.84(11)
C11 C10 C1' 112.5(6)
C15 C10 C1' 128.8(6)
C10 C11 C12 120.53(11)
C10 C11 H11A 119.7
C12 C11 H11A 119.7
C13 C12 C11 120.32(12)
C13 C12 H12A 119.8
C11 C12 H12A 119.8
C14 C13 C12 119.56(11)
C14 C13 H13A 120.2
C12 C13 H13A 120.2
C13 C14 C15 120.21(11)
C13 C14 H14A 119.9
C15 C14 H14A 119.9
C14 C15 C10 120.74(11)
C14 C15 H15A 119.6
C10 C15 H15A 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.292(2)
N1 C9 1.457(3)
C1 C3 1.490(2)
C1 C2 1.5224(17)
C2 H2A 0.9800
C2 H2B 0.9800
C2 H2C 0.9800
C9 C10 1.510(2)
C9 H9A 0.9900
C9 H9B 0.9900
N1' C1' 1.289(18)
N1' C9' 1.457(19)
C1' C2' 1.516(16)
C1' C10 1.60(2)
C2' H2'A 0.9800
C2' H2'B 0.9800
C2' H2'C 0.9800
C9' C3 1.66(2)
C9' H9'A 0.9900
C9' H9'B 0.9900
C3 C4 1.3971(15)
C3 C8 1.4020(15)
C4 C5 1.3908(16)
C4 H4A 0.9500
C5 C6 1.3876(17)
C5 H5A 0.9500
C6 C7 1.3932(16)
C6 H6A 0.9500
C7 C8 1.3855(16)
C7 H7A 0.9500
C8 H8A 0.9500
C10 C11 1.3911(17)
C10 C15 1.3952(16)
C11 C12 1.3938(17)
C11 H11A 0.9500
C12 C13 1.3877(17)
C12 H12A 0.9500
C13 C14 1.3828(18)
C13 H13A 0.9500
C14 C15 1.3920(16)
C14 H14A 0.9500
C15 H15A 0.9500
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
C9 N1 C1 C3 177.6(2)
C9 N1 C1 C2 -3.0(4)
C1 N1 C9 C10 176.2(3)
C9' N1' C1' C2' -26(5)
C9' N1' C1' C10 174(2)
C1' N1' C9' C3 -170(3)
N1 C1 C3 C4 177.9(2)
C2 C1 C3 C4 -1.5(2)
N1 C1 C3 C8 -1.6(3)
C2 C1 C3 C8 179.08(12)
N1 C1 C3 C9' 180(6)
C2 C1 C3 C9' 0(5)
N1' C9' C3 C4 -175(2)
N1' C9' C3 C8 5(3)
N1' C9' C3 C1 7(5)
C8 C3 C4 C5 0.44(17)
C1 C3 C4 C5 -179.01(13)
C9' C3 C4 C5 -179.4(10)
C3 C4 C5 C6 -0.23(18)
C4 C5 C6 C7 -0.05(18)
C5 C6 C7 C8 0.10(18)
C6 C7 C8 C3 0.12(18)
C4 C3 C8 C7 -0.39(16)
C1 C3 C8 C7 179.07(12)
C9' C3 C8 C7 179.4(12)
N1 C9 C10 C11 -8.5(3)
N1 C9 C10 C15 172.2(2)
N1 C9 C10 C1' -9(5)
N1' C1' C10 C11 -22(4)
C2' C1' C10 C11 175.3(10)
N1' C1' C10 C15 159(3)
C2' C1' C10 C15 -4(2)
N1' C1' C10 C9 158(8)
C2' C1' C10 C9 -5(4)
C15 C10 C11 C12 -1.24(19)
C9 C10 C11 C12 179.41(15)
C1' C10 C11 C12 179.5(10)
C10 C11 C12 C13 0.2(2)
C11 C12 C13 C14 0.92(19)
C12 C13 C14 C15 -1.07(19)
C13 C14 C15 C10 0.05(19)
C11 C10 C15 C14 1.10(18)
C9 C10 C15 C14 -179.51(14)
C1' C10 C15 C14 -179.8(12)
