#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/75/2227502.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_2227502
loop_
_publ_author_name
'Tahir, M. Nawaz'
'Tariq, Muhammad Ilyas'
'Ahmad, Shahbaz'
'Sarfraz, Muhammad'
'Tariq, Riaz H.'
_publ_section_title
;
 2,3-Dimethyl-N-[(E)-(1H-pyrrol-2-yl)methylidene]aniline
;
_journal_coeditor_code           HB5606
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2295
_journal_paper_doi               10.1107/S1600536810031867
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H14 N2'
_chemical_formula_moiety         'C13 H14 N2'
_chemical_formula_sum            'C13 H14 N2'
_chemical_formula_weight         198.26
_chemical_name_systematic
;
2,3-Dimethyl-N-[(E)-(1H-pyrrol-2-yl)methylidene]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
_cell_angle_beta                 107.613(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8684(9)
_cell_length_b                   7.1649(5)
_cell_length_c                   12.9517(9)
_cell_measurement_reflns_used    1075
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.25
_cell_measurement_theta_min      3.21
_cell_volume                     1138.18(14)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.10
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_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  0.0647
_diffrn_reflns_av_sigmaI/netI    0.0659
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8641
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         3.21
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.127
_refine_ls_extinction_coef       0.019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2066
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1182
_refine_ls_R_factor_gt           0.0518
_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)+(0.0559P)²+0.0942P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1415
_reflns_number_gt                1075
_reflns_number_total             2066
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5606.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227502
_cod_database_fobs_code          2227502
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
N N1 0.39549(16) 0.8356(3) 0.05111(16) 0.0532(8) Uani . . 1.000
N N2 0.62151(16) 0.9535(3) 0.15496(16) 0.0550(8) Uani . . 1.000
C C1 0.2837(2) 0.7796(3) 0.01500(19) 0.0499(9) Uani . . 1.000
C C2 0.25093(19) 0.6419(4) -0.06368(19) 0.0539(9) Uani . . 1.000
C C3 0.1406(2) 0.5922(4) -0.1006(2) 0.0659(11) Uani . . 1.000
C C4 0.0680(2) 0.6814(4) -0.0579(3) 0.0787(11) Uani . . 1.000
C C5 0.1015(2) 0.8157(4) 0.0209(3) 0.0834(14) Uani . . 1.000
C C6 0.2096(2) 0.8668(4) 0.0569(2) 0.0675(11) Uani . . 1.000
C C7 0.3339(2) 0.5434(4) -0.1043(2) 0.0766(11) Uani . . 1.000
C C8 0.0995(3) 0.4408(5) -0.1836(2) 0.1085(16) Uani . . 1.000
C C9 0.44692(19) 0.8048(3) 0.1505(2) 0.0516(9) Uani . . 1.000
C C10 0.55763(19) 0.8560(3) 0.20329(18) 0.0495(9) Uani . . 1.000
C C11 0.6209(2) 0.8162(3) 0.3068(2) 0.0592(10) Uani . . 1.000
C C12 0.7242(2) 0.8895(4) 0.3205(2) 0.0642(10) Uani . . 1.000
C C13 0.7225(2) 0.9738(4) 0.2261(2) 0.0635(10) Uani . . 1.000
H H2 0.60086 0.99538 0.08967 0.0660 Uiso . . 1.000
H H4 -0.00546 0.64985 -0.08297 0.0945 Uiso . . 1.000
H H5 0.05137 0.87191 0.04976 0.1003 Uiso . . 1.000
H H6 0.23263 0.95956 0.10904 0.0810 Uiso . . 1.000
H H7A 0.39874 0.61809 -0.08930 0.1147 Uiso . . 1.000
H H7B 0.30476 0.52419 -0.18105 0.1147 Uiso . . 1.000
H H7C 0.35134 0.42497 -0.06860 0.1147 Uiso . . 1.000
H H8A 0.13149 0.32366 -0.15456 0.1628 Uiso . . 1.000
H H8B 0.11924 0.46977 -0.24760 0.1628 Uiso . . 1.000
H H8C 0.02160 0.43251 -0.20160 0.1628 Uiso . . 1.000
H H9 0.40938 0.74430 0.19188 0.0620 Uiso . . 1.000
H H11 0.59856 0.75163 0.35870 0.0711 Uiso . . 1.000
H H12 0.78356 0.88212 0.38276 0.0770 Uiso . . 1.000
H H13 0.78071 1.03508 0.21258 0.0763 Uiso . . 1.000
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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C9 . . . 116.4(2) yes
C10 N2 C13 . . . 109.3(2) yes
C10 N2 H2 . . . 125.00 no
C13 N2 H2 . . . 125.00 no
N1 C1 C2 . . . 119.5(2) yes
N1 C1 C6 . . . 119.4(2) yes
C2 C1 C6 . . . 121.1(2) no
C1 C2 C3 . . . 118.9(2) no
C3 C2 C7 . . . 121.1(2) no
C1 C2 C7 . . . 120.0(2) no
C2 C3 C8 . . . 121.9(3) no
C4 C3 C8 . . . 119.1(3) no
C2 C3 C4 . . . 119.0(3) no
C3 C4 C5 . . . 121.6(3) no
C4 C5 C6 . . . 119.7(3) no
C1 C6 C5 . . . 119.6(3) no
N1 C9 C10 . . . 125.2(2) yes
N2 C10 C11 . . . 107.0(2) yes
C9 C10 C11 . . . 128.7(2) no
N2 C10 C9 . . . 124.3(2) yes
C10 C11 C12 . . . 108.0(2) no
C11 C12 C13 . . . 107.4(2) no
N2 C13 C12 . . . 108.4(2) yes
C3 C4 H4 . . . 119.00 no
C5 C4 H4 . . . 119.00 no
C4 C5 H5 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
C1 C6 H6 . . . 120.00 no
C5 C6 H6 . . . 120.00 no
C2 C7 H7A . . . 109.00 no
C2 C7 H7B . . . 109.00 no
C2 C7 H7C . . . 110.00 no
H7A C7 H7B . . . 109.00 no
H7A C7 H7C . . . 109.00 no
H7B C7 H7C . . . 109.00 no
C3 C8 H8A . . . 109.00 no
C3 C8 H8B . . . 109.00 no
C3 C8 H8C . . . 109.00 no
H8A C8 H8B . . . 109.00 no
H8A C8 H8C . . . 109.00 no
H8B C8 H8C . . . 109.00 no
N1 C9 H9 . . . 117.00 no
C10 C9 H9 . . . 117.00 no
C10 C11 H11 . . . 126.00 no
C12 C11 H11 . . . 126.00 no
C11 C12 H12 . . . 126.00 no
C13 C12 H12 . . . 126.00 no
N2 C13 H13 . . . 126.00 no
C12 C13 H13 . . . 126.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 . . 1.429(3) yes
N1 C9 . . 1.276(3) yes
N2 C10 . . 1.366(3) yes
N2 C13 . . 1.354(3) yes
N2 H2 . . 0.8600 no
C1 C2 . . 1.389(3) no
C1 C6 . . 1.381(4) no
C2 C7 . . 1.502(4) no
C2 C3 . . 1.400(4) no
C3 C4 . . 1.378(4) no
C3 C8 . . 1.506(4) no
C4 C5 . . 1.374(5) no
C5 C6 . . 1.376(4) no
C9 C10 . . 1.429(4) no
C10 C11 . . 1.372(3) no
C11 C12 . . 1.390(4) no
C12 C13 . . 1.358(4) no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C6 H6 . . 0.9300 no
C7 H7A . . 0.9600 no
C7 H7B . . 0.9600 no
C7 H7C . . 0.9600 no
C8 H8A . . 0.9600 no
C8 H8B . . 0.9600 no
C8 H8C . . 0.9600 no
C9 H9 . . 0.9300 no
C11 H11 . . 0.9300 no
C12 H12 . . 0.9300 no
C13 H13 . . 0.9300 no
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
_geom_hbond_publ_flag
N2 H2 N1 3_675 0.86 2.20 3.017(3) 158 yes
C9 H9 Cg1 2_645 0.93 2.80 3.606(3) 145 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 N1 C1 C2 . . . . -116.5(3) no
C9 N1 C1 C6 . . . . 65.2(3) no
C1 N1 C9 C10 . . . . -177.7(2) no
C13 N2 C10 C9 . . . . -178.2(2) no
C13 N2 C10 C11 . . . . 0.3(3) no
C10 N2 C13 C12 . . . . 0.0(3) no
N1 C1 C2 C3 . . . . -178.2(2) no
N1 C1 C2 C7 . . . . 4.4(4) no
C6 C1 C2 C3 . . . . 0.1(4) no
C6 C1 C2 C7 . . . . -177.3(2) no
N1 C1 C6 C5 . . . . 178.8(2) no
C2 C1 C6 C5 . . . . 0.5(4) no
C1 C2 C3 C4 . . . . 0.1(4) no
C1 C2 C3 C8 . . . . -178.4(2) no
C7 C2 C3 C4 . . . . 177.5(3) no
C7 C2 C3 C8 . . . . -1.0(4) no
C2 C3 C4 C5 . . . . -0.9(5) no
C8 C3 C4 C5 . . . . 177.6(3) no
C3 C4 C5 C6 . . . . 1.6(5) no
C4 C5 C6 C1 . . . . -1.4(4) no
N1 C9 C10 N2 . . . . 3.4(4) no
N1 C9 C10 C11 . . . . -174.7(2) no
N2 C10 C11 C12 . . . . -0.4(3) no
C9 C10 C11 C12 . . . . 177.9(2) no
C10 C11 C12 C13 . . . . 0.5(3) no
C11 C12 C13 N2 . . . . -0.3(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745772
