#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/91/2019115.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_2019115
loop_
_publ_author_name
'Su, Bi-Yun'
'Wang, Jia-Xiang'
'Liu, Xiang'
'Li, Qian-Ding'
_publ_section_title
;
 3,4-Dimethyl-N-[1-(1H-pyrrol-2-yl)ethylidene]aniline and
 the 1-(1-thiophen-2-yl) analogue
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1073
_journal_page_last               1076
_journal_paper_doi               10.1107/S0108270113022142
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C14 H16 N2'
_chemical_formula_moiety         'C14 H16 N2'
_chemical_formula_sum            'C14 H16 N2'
_chemical_formula_weight         212.29
_chemical_name_systematic
;
3,4-Dimethyl-N-[1-(1H-pyrrol-2-yl)ethylidene]aniline
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 110.448(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.013(3)
_cell_length_b                   10.265(2)
_cell_length_c                   9.892(2)
_cell_measurement_reflns_used    838
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.54
_cell_measurement_theta_min      2.59
_cell_volume                     1238.1(5)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.978
_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  0.0468
_diffrn_reflns_av_sigmaI/netI    0.0527
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6774
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.86
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_correction_T_min  0.9750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2603
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.1157
_refine_ls_R_factor_gt           0.0561
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1501
_refine_ls_wR_factor_ref         0.1894
_reflns_number_gt                1344
_reflns_number_total             2603
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cu3033.cif
_cod_data_source_block           I
_cod_original_cell_volume        1238.2(4)
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               2019115
_cod_database_fobs_code          2019115
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
N N1 -0.17111(16) 0.46605(19) -0.02161(19) 0.0606(5) Uani d . 1 1
H H1 -0.1169(19) 0.500(2) -0.040(2) 0.073 Uiso d . 1 1
N N2 0.03340(15) 0.40619(18) 0.18907(18) 0.0643(6) Uani d . 1 1
C C1 -0.27753(19) 0.4720(2) -0.1073(3) 0.0723(7) Uani d . 1 1
H H1A -0.3055 0.5154 -0.1951 0.087 Uiso calc R 1 1
C C2 -0.3370(2) 0.4029(3) -0.0421(3) 0.0795(8) Uani d . 1 1
H H2 -0.4126 0.3911 -0.0773 0.095 Uiso calc R 1 1
C C3 -0.2642(2) 0.3534(3) 0.0862(3) 0.0748(7) Uani d . 1 1
H H3 -0.2824 0.3022 0.1521 0.090 Uiso calc R 1 1
C C4 -0.15956(18) 0.3937(2) 0.0987(2) 0.0579(6) Uani d . 1 1
C C5 -0.0541(2) 0.3664(2) 0.2080(2) 0.0594(6) Uani d . 1 1
C C6 -0.0547(2) 0.2908(3) 0.3394(3) 0.0915(9) Uani d . 1 1
H H6A -0.0256 0.2051 0.3377 0.137 Uiso calc R 1 1
H H6B -0.1286 0.2840 0.3384 0.137 Uiso calc R 1 1
H H6C -0.0104 0.3353 0.4253 0.137 Uiso calc R 1 1
C C7 0.13719(19) 0.3741(2) 0.2936(2) 0.0601(6) Uani d . 1 1
C C8 0.1881(2) 0.2577(2) 0.2830(2) 0.0744(7) Uani d . 1 1
H H8 0.1532 0.1986 0.2102 0.089 Uiso calc R 1 1
C C9 0.2905(2) 0.2303(3) 0.3809(3) 0.0795(8) Uani d . 1 1
H H9 0.3231 0.1514 0.3731 0.095 Uiso calc R 1 1
C C10 0.34727(19) 0.3147(3) 0.4904(2) 0.0689(7) Uani d . 1 1
C C11 0.2978(2) 0.4342(2) 0.4993(2) 0.0642(6) Uani d . 1 1
C C12 0.1935(2) 0.4612(2) 0.4006(2) 0.0648(6) Uani d . 1 1
H H12 0.1608 0.5404 0.4069 0.078 Uiso calc R 1 1
C C13 0.4574(2) 0.2778(3) 0.5978(3) 0.0988(9) Uani d . 1 1
H H13A 0.4773 0.1926 0.5755 0.148 Uiso calc R 1 1
H H13B 0.4538 0.2775 0.6931 0.148 Uiso calc R 1 1
H H13C 0.5114 0.3398 0.5935 0.148 Uiso calc R 1 1
C C14 0.3561(2) 0.5324(3) 0.6135(3) 0.0956(9) Uani d . 1 1
H H14A 0.3130 0.6105 0.5992 0.143 Uiso calc R 1 1
H H14B 0.4263 0.5521 0.6071 0.143 Uiso calc R 1 1
H H14C 0.3660 0.4970 0.7071 0.143 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
_geom_angle_publ_flag
C1 N1 C4 110.39(19) y
C1 N1 H1 126.0(15) ?
C4 N1 H1 123.6(15) ?
C5 N2 C7 119.03(18) ?
N1 C1 C2 107.8(2) y
N1 C1 H1A 126.1 ?
C2 C1 H1A 126.1 ?
C1 C2 C3 107.7(2) y
C1 C2 H2 126.2 ?
C3 C2 H2 126.2 ?
C2 C3 C4 107.9(2) y
C2 C3 H3 126.0 ?
C4 C3 H3 126.0 ?
N1 C4 C3 106.2(2) y
N1 C4 C5 122.9(2) y
C3 C4 C5 130.9(2) y
N2 C5 C4 119.17(19) y
N2 C5 C6 124.0(2) ?
C4 C5 C6 116.9(2) ?
C5 C6 H6A 109.5 ?
C5 C6 H6B 109.5 ?
H6A C6 H6B 109.5 ?
C5 C6 H6C 109.5 ?
H6A C6 H6C 109.5 ?
H6B C6 H6C 109.5 ?
C12 C7 C8 118.3(2) ?
C12 C7 N2 121.4(2) ?
C8 C7 N2 120.1(2) ?
C9 C8 C7 119.6(2) ?
C9 C8 H8 120.2 ?
C7 C8 H8 120.2 ?
C8 C9 C10 123.0(2) ?
C8 C9 H9 118.5 ?
C10 C9 H9 118.5 ?
C9 C10 C11 117.8(2) ?
C9 C10 C13 120.9(2) ?
C11 C10 C13 121.4(2) ?
C12 C11 C10 119.0(2) ?
C12 C11 C14 120.3(2) ?
C10 C11 C14 120.7(2) ?
C7 C12 C11 122.2(2) ?
C7 C12 H12 118.9 ?
C11 C12 H12 118.9 ?
C10 C13 H13A 109.5 ?
C10 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
C10 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
C11 C14 H14A 109.5 ?
C11 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
C11 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 1.349(3) y
N1 C4 1.366(3) y
N1 H1 0.86(2) ?
N2 C5 1.284(3) y
N2 C7 1.423(3) y
C1 C2 1.367(3) y
C1 H1A 0.9300 ?
C2 C3 1.387(3) y
C2 H2 0.9300 ?
C3 C4 1.387(3) y
C3 H3 0.9300 ?
C4 C5 1.447(3) y
C5 C6 1.517(3) ?
C6 H6A 0.9600 ?
C6 H6B 0.9600 ?
C6 H6C 0.9600 ?
C7 C12 1.384(3) ?
C7 C8 1.388(3) ?
C8 C9 1.375(3) ?
C8 H8 0.9300 ?
C9 C10 1.382(3) ?
C9 H9 0.9300 ?
C10 C11 1.403(3) ?
C10 C13 1.505(3) ?
C11 C12 1.395(3) ?
C11 C14 1.506(3) ?
C12 H12 0.9300 ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 N2 3_565 0.86(2) 2.33(2) 3.122(3) 154(2)
C1 H1A Cg1 3_565 0.93 2.76 3.537(6) 142.2
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_publ_flag
C4 N1 C1 C2 0.2(3) ?
N1 C1 C2 C3 -0.3(3) ?
C1 C2 C3 C4 0.3(3) ?
C1 N1 C4 C3 0.0(3) ?
C1 N1 C4 C5 177.7(2) ?
C2 C3 C4 N1 -0.1(3) ?
C2 C3 C4 C5 -177.6(2) ?
C7 N2 C5 C4 -177.21(18) ?
C7 N2 C5 C6 2.6(3) ?
N1 C4 C5 N2 -3.3(3) y
C3 C4 C5 N2 173.8(2) ?
N1 C4 C5 C6 176.8(2) ?
C3 C4 C5 C6 -6.0(4) ?
C5 N2 C7 C12 -97.8(3) ?
C5 N2 C7 C8 87.4(3) y
C12 C7 C8 C9 2.1(3) ?
N2 C7 C8 C9 177.1(2) ?
C7 C8 C9 C10 -0.8(4) ?
C8 C9 C10 C11 -1.0(4) ?
C8 C9 C10 C13 177.8(2) ?
C9 C10 C11 C12 1.5(3) ?
C13 C10 C11 C12 -177.3(2) ?
C9 C10 C11 C14 -178.4(2) ?
C13 C10 C11 C14 2.7(3) ?
C8 C7 C12 C11 -1.6(3) ?
N2 C7 C12 C11 -176.56(19) ?
C10 C11 C12 C7 -0.2(3) ?
C14 C11 C12 C7 179.7(2) ?
