#------------------------------------------------------------------------------
#$Date: 2017-10-13 13:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201982 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/24/4102498.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_4102498
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           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                 93.874(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2311(8)
_cell_length_b                   7.3758(7)
_cell_length_c                   15.2252(15)
_cell_measurement_temperature    103(2)
_cell_volume                     922.22(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1883
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.2*0.2*0.1
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.291
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1883
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.291
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0823
_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)+(0.0394P)²+1.2201P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1680
_refine_ls_wR_factor_ref         0.1693
_reflns_number_gt                1822
_reflns_number_total             1883
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja101336n_si_004.cif
_cod_data_source_block           z2
_cod_database_code               4102498
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_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
_atom_site_refinement_flags
N1 N 0.2844(2) 0.1675(3) 0.77767(14) 0.0258(5) Uani 1 1 d .
N2 N 0.9285(3) 0.1665(3) 1.07870(15) 0.0312(5) Uani 1 1 d .
C1 C 0.4118(3) 0.1569(3) 0.84062(16) 0.0222(5) Uani 1 1 d .
C2 C 0.4020(3) 0.2430(3) 0.92363(16) 0.0224(5) Uani 1 1 d .
C3 C 0.2455(3) 0.3292(4) 0.94740(17) 0.0266(6) Uani 1 1 d .
H3A H 0.2701 0.4365 0.9850 0.032 Uiso 1 1 calc R
H3B H 0.1834 0.2419 0.9815 0.032 Uiso 1 1 calc R
C4 C 0.1420(3) 0.3870(4) 0.86487(18) 0.0319(6) Uani 1 1 d .
H4A H 0.0327 0.4250 0.8813 0.038 Uiso 1 1 calc R
H4B H 0.1937 0.4917 0.8371 0.038 Uiso 1 1 calc R
C5 C 0.1257(3) 0.2320(4) 0.80059(18) 0.0315(6) Uani 1 1 d .
H5A H 0.0657 0.1314 0.8268 0.038 Uiso 1 1 calc R
H5B H 0.0620 0.2721 0.7466 0.038 Uiso 1 1 calc R
C6 C 0.2897(3) 0.0667(4) 0.69661(18) 0.0347(7) Uani 1 1 d .
H6A H 0.3917 0.0930 0.6695 0.052 Uiso 1 1 calc R
H6B H 0.1974 0.1020 0.6562 0.052 Uiso 1 1 calc R
H6C H 0.2834 -0.0634 0.7091 0.052 Uiso 1 1 calc R
C7 C 0.5564(3) 0.0642(3) 0.82393(16) 0.0249(6) Uani 1 1 d .
H7A H 0.5627 0.0002 0.7701 0.030 Uiso 1 1 calc R
C8 C 0.6889(3) 0.0648(3) 0.88463(16) 0.0245(5) Uani 1 1 d .
H8A H 0.7854 0.0021 0.8720 0.029 Uiso 1 1 calc R
C9 C 0.6821(3) 0.1568(3) 0.96432(16) 0.0225(5) Uani 1 1 d .
C10 C 0.5371(3) 0.2433(3) 0.98279(16) 0.0232(5) Uani 1 1 d .
H10A H 0.5313 0.3039 1.0375 0.028 Uiso 1 1 calc R
C11 C 0.8198(3) 0.1611(3) 1.02761(16) 0.0246(6) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0227(10) 0.0279(11) 0.0260(11) 0.0017(9) -0.0040(8) -0.0006(9)
N2 0.0230(11) 0.0352(13) 0.0343(12) -0.0062(10) -0.0074(9) 0.0045(9)
C1 0.0219(12) 0.0214(12) 0.0232(12) 0.0053(10) -0.0002(9) -0.0048(9)
C2 0.0174(11) 0.0202(12) 0.0299(13) 0.0054(10) 0.0023(9) 0.0004(9)
C3 0.0223(12) 0.0295(13) 0.0282(13) -0.0018(11) 0.0045(10) 0.0044(10)
C4 0.0239(13) 0.0336(15) 0.0381(15) 0.0036(12) 0.0022(11) 0.0123(11)
C5 0.0223(12) 0.0383(15) 0.0328(14) 0.0055(12) -0.0051(10) 0.0026(11)
C6 0.0303(14) 0.0430(17) 0.0296(14) -0.0086(12) -0.0074(11) -0.0014(12)
C7 0.0264(12) 0.0265(13) 0.0217(12) -0.0011(10) 0.0008(10) -0.0022(10)
C8 0.0185(11) 0.0237(13) 0.0311(13) 0.0010(10) 0.0009(10) 0.0002(10)
C9 0.0187(11) 0.0218(12) 0.0263(12) 0.0030(10) -0.0032(9) -0.0023(9)
C10 0.0230(12) 0.0246(13) 0.0220(12) -0.0005(10) 0.0012(9) -0.0012(10)
C11 0.0220(12) 0.0226(12) 0.0293(13) -0.0027(10) 0.0014(10) 0.0025(10)
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 C6 120.1(2)
C1 N1 C5 120.4(2)
C6 N1 C5 116.9(2)
N1 C1 C7 121.0(2)
N1 C1 C2 120.6(2)
C7 C1 C2 118.4(2)
C10 C2 C1 119.2(2)
C10 C2 C3 120.5(2)
C1 C2 C3 120.3(2)
C2 C3 C4 111.0(2)
C5 C4 C3 110.0(2)
N1 C5 C4 111.2(2)
C8 C7 C1 121.0(2)
C7 C8 C9 120.5(2)
C8 C9 C10 118.8(2)
C8 C9 C11 121.2(2)
C10 C9 C11 120.0(2)
C2 C10 C9 121.9(2)
N2 C11 C9 179.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.374(3)
N1 C6 1.444(3)
N1 C5 1.455(3)
N2 C11 1.146(3)
C1 C7 1.411(3)
C1 C2 1.422(3)
C2 C10 1.383(3)
C2 C3 1.502(3)
C3 C4 1.531(3)
C4 C5 1.505(4)
C7 C8 1.381(3)
C8 C9 1.395(3)
C9 C10 1.398(3)
C9 C11 1.438(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 27224669
