#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/25/4102500.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_4102500
loop_
_publ_author_name
'Sergey I. Druzhinin'
'Peter Mayer'
'Dietmar Stalke'
'Rixa von Bülow'
'Mathias Noltemeyer'
'Klaas A. Zachariasse'
_publ_contact_author_address
;
Max-Planck-Institut fuer biophysikalische Chemie, Spektroskopie und 
Photochemische Kinetik
D-37070 Goettingen
Germany
;
_publ_contact_author_email       kzachar@gwdg.de
_publ_contact_author_name        'Klaas A. Zachariasse'
_publ_section_title
;
 Intramolecular Charge Transfer with
 1-tert-Butyl-6-cyano-1,2,3,4-tetrahydroquinoline (NTC6) and Other
 Aminobenzonitriles. A Comparison of Experimental Vapor Phase Spectra and
 Crystal Structures with Calculations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7730
_journal_page_last               7744
_journal_paper_doi               10.1021/ja101336n
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C11 H12 N2'
_chemical_formula_weight         172.23
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.5057(5)
_cell_length_b                   8.4820(5)
_cell_length_c                   19.2656(12)
_cell_measurement_temperature    200(2)
_cell_volume                     1880.16(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0521
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11005
_diffrn_reflns_theta_full        25.33
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    0.074
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         1715
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0430
_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)+(0.0613P)²+0.1389P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1225
_reflns_number_gt                1149
_reflns_number_total             1715
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja101336n_si_006.cif
_cod_data_source_block           ln513
_cod_database_code               4102500
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
N1 N 0.09802(13) 0.47406(18) 0.35765(8) 0.0536(5) Uani 1 1 d
N2 N 0.09681(16) 0.9183(2) 0.64439(9) 0.0719(6) Uani 1 1 d
C1 C -0.00283(17) 0.5285(2) 0.31930(10) 0.0544(5) Uani 1 1 d
C2 C -0.04903(17) 0.6690(3) 0.35949(10) 0.0548(5) Uani 1 1 d
C3 C 0.02471(13) 0.67252(19) 0.42384(8) 0.0427(5) Uani 1 1 d
C4 C 0.10987(14) 0.5543(2) 0.41813(9) 0.0436(5) Uani 1 1 d
C5 C 0.19220(15) 0.5323(2) 0.47049(9) 0.0495(5) Uani 1 1 d
C6 C 0.18576(15) 0.6259(2) 0.52866(10) 0.0496(5) Uani 1 1 d
C7 C 0.10056(14) 0.74218(19) 0.53541(8) 0.0443(5) Uani 1 1 d
C8 C 0.01895(15) 0.7653(2) 0.48186(9) 0.0455(5) Uani 1 1 d
C9 C 0.09736(16) 0.8391(2) 0.59584(10) 0.0529(5) Uani 1 1 d
C10 C 0.16397(18) 0.3369(2) 0.33666(11) 0.0565(5) Uani 1 1 d
C11 C 0.2663(2) 0.3766(3) 0.29172(14) 0.0692(6) Uani 1 1 d
H8 H -0.0426(17) 0.844(2) 0.4880(8) 0.059(5) Uiso 1 1 d
H21 H -0.131(2) 0.658(2) 0.3682(10) 0.068(6) Uiso 1 1 d
H6 H 0.2401(15) 0.6145(19) 0.5652(9) 0.048(4) Uiso 1 1 d
H5 H 0.2500(18) 0.452(2) 0.4671(8) 0.058(5) Uiso 1 1 d
H22 H -0.0425(17) 0.769(2) 0.3308(10) 0.072(6) Uiso 1 1 d
H101 H 0.1911(18) 0.281(2) 0.3791(12) 0.074(6) Uiso 1 1 d
H102 H 0.1071(19) 0.264(2) 0.3118(11) 0.076(6) Uiso 1 1 d
H11 H 0.0163(17) 0.553(2) 0.2722(11) 0.068(6) Uiso 1 1 d
H111 H 0.324(2) 0.445(3) 0.3203(12) 0.090(7) Uiso 1 1 d
H12 H -0.0607(19) 0.436(3) 0.3179(10) 0.080(6) Uiso 1 1 d
H112 H 0.303(2) 0.285(3) 0.2773(12) 0.097(8) Uiso 1 1 d
H113 H 0.242(2) 0.438(3) 0.2498(13) 0.089(7) Uiso 1 1 d
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
C4 N1 C10 126.22(16)
C4 N1 C1 111.00(15)
C10 N1 C1 122.20(16)
N1 C1 C2 105.67(15)
N1 C1 H11 111.6(12)
C2 C1 H11 113.2(12)
N1 C1 H12 106.7(11)
C2 C1 H12 112.7(11)
H11 C1 H12 106.9(17)
C3 C2 C1 103.80(15)
C3 C2 H21 114.3(12)
C1 C2 H21 110.7(12)
C3 C2 H22 113.0(11)
C1 C2 H22 110.7(11)
H21 C2 H22 104.6(17)
C8 C3 C4 120.51(15)
C8 C3 C2 131.14(16)
C4 C3 C2 108.35(15)
N1 C4 C5 128.47(16)
N1 C4 C3 110.79(14)
C5 C4 C3 120.74(16)
C6 C5 C4 118.38(17)
C6 C5 H5 120.4(10)
C4 C5 H5 121.2(10)
C5 C6 C7 121.42(16)
C5 C6 H6 120.8(10)
C7 C6 H6 117.8(10)
C6 C7 C8 119.84(16)
C6 C7 C9 120.09(15)
C8 C7 C9 120.06(16)
C3 C8 C7 119.09(16)
C3 C8 H8 121.7(10)
C7 C8 H8 119.2(10)
N2 C9 C7 178.7(2)
N1 C10 C11 113.14(18)
N1 C10 H101 108.4(12)
C11 C10 H101 109.5(12)
N1 C10 H102 106.4(11)
C11 C10 H102 111.6(12)
H101 C10 H102 107.5(16)
C10 C11 H111 108.8(13)
C10 C11 H112 110.1(15)
H111 C11 H112 109.6(19)
C10 C11 H113 111.5(14)
H111 C11 H113 108.2(19)
H112 C11 H113 108.6(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C4 1.356(2)
N1 C10 1.446(2)
N1 C1 1.451(2)
N2 C9 1.152(2)
C1 C2 1.518(3)
C1 H11 0.96(2)
C1 H12 1.03(2)
C2 C3 1.503(2)
C2 H21 0.96(2)
C2 H22 1.02(2)
C3 C8 1.368(2)
C3 C4 1.406(2)
C4 C5 1.396(2)
C5 C6 1.375(3)
C5 H5 0.96(2)
C6 C7 1.397(2)
C6 H6 0.947(18)
C7 C8 1.409(2)
C7 C9 1.425(3)
C8 H8 0.98(2)
C10 C11 1.499(3)
C10 H101 0.99(2)
C10 H102 1.02(2)
C11 H111 1.04(3)
C11 H112 0.93(3)
C11 H113 1.00(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
C4 N1 C1 C2 6.0(2)
C10 N1 C1 C2 177.76(16)
N1 C1 C2 C3 -6.0(2)
C1 C2 C3 C8 -174.73(17)
C1 C2 C3 C4 4.2(2)
C10 N1 C4 C5 5.6(3)
C1 N1 C4 C5 176.95(18)
C10 N1 C4 C3 -174.76(16)
C1 N1 C4 C3 -3.4(2)
C8 C3 C4 N1 178.35(15)
C2 C3 C4 N1 -0.76(19)
C8 C3 C4 C5 -1.9(2)
C2 C3 C4 C5 178.96(16)
N1 C4 C5 C6 -178.37(16)
C3 C4 C5 C6 2.0(2)
C4 C5 C6 C7 -1.0(2)
C5 C6 C7 C8 0.0(2)
C5 C6 C7 C9 -178.94(16)
C4 C3 C8 C7 0.9(2)
C2 C3 C8 C7 179.77(17)
C6 C7 C8 C3 0.0(2)
C9 C7 C8 C3 179.01(15)
C6 C7 C9 N2 60(9)
C8 C7 C9 N2 -119(9)
C4 N1 C10 C11 -95.6(2)
C1 N1 C10 C11 93.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 28706290
