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#$Date: 2016-01-06 12:34:23 +0200 (Wed, 06 Jan 2016) $
#$Revision: 173599 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/05/1540571.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_1540571
loop_
_publ_author_name
'Druzhinin, Sergey I.'
'Galievsky, Victor A.'
'Demeter, Attila'
'Kovalenko, Sergey A.'
'Senyushkina, Tamara'
'Dubbaka, Srinivas R.'
'Knochel, Paul'
'Mayer, Peter'
'Grosse, Christian'
'Stalke, Dietmar'
'Zachariasse, Klaas A.'
_publ_section_title
;
 Two-State Intramolecular Charge Transfer (ICT) with
 3,5-Dimethyl-4-(dimethylamino)benzonitrile (MMD) and Its Meta-Isomer
 mMMD. Ground State Amino Twist Not Essential for ICT.
;
_journal_issue                   49
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              11820
_journal_page_last               11836
_journal_paper_doi               10.1021/acs.jpca.5b09368
_journal_volume                  119
_journal_year                    2015
_chemical_formula_moiety         'C11 H14 N2'
_chemical_formula_sum            'C11 H14 N2'
_chemical_formula_weight         174.242
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      62
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                C11H14N2_mn265_zachariasse
_audit_creation_date             18-Jul-08
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_audit_update_record             18-Jul-08
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9170(4)
_cell_length_b                   7.6126(3)
_cell_length_c                   15.0884(6)
_cell_measurement_reflns_used    7754
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      3.134
_cell_volume                     1024.22(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement
'SHELXL-97 (G. M. Sheldrick. University of Göttingen, 97-2 version)'
_computing_structure_solution
;
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A.
Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for
crystal structure determination and refinement; J. Appl. Crystallogr. 1999,
32, 115-119.
;
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method
'CCD, rotation images, thick slices, phi/omega-scan'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.0511404
_diffrn_orient_matrix_UB_12      0.0317310
_diffrn_orient_matrix_UB_13      -0.0580957
_diffrn_orient_matrix_UB_21      -0.1072521
_diffrn_orient_matrix_UB_22      0.0375169
_diffrn_orient_matrix_UB_23      0.0311896
_diffrn_orient_matrix_UB_31      0.0560126
_diffrn_orient_matrix_UB_32      0.1008078
_diffrn_orient_matrix_UB_33      0.0066791
_diffrn_radiation_collimation    0.20
_diffrn_radiation_monochromator  'MONTEL, graded multilayered X-ray optics'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6109
_diffrn_reflns_theta_full        25.23
_diffrn_reflns_theta_max         25.23
_diffrn_reflns_theta_min         3.54
_diffrn_source_current           55.00
_diffrn_source_power             3.025
_diffrn_source_type              'FR 591 generator'
_diffrn_source_voltage           55.00
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.12999(8)
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.04(2)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     80
_refine_ls_number_reflns         992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0641
_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)+(0.0730P)²+0.4534P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1708
_refine_ls_wR_factor_ref         0.1785
_reflns_number_gt                782
_reflns_number_total             992
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp5b09368_si_001.cif
_cod_data_source_block           mn265
_cod_depositor_comments
'Adding full bibliography for 1540571--1540573.cif.'
_cod_database_code               1540571
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -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
_atom_site_refinement_flags
N7 N 0.8098(3) 0.2500 0.16068(15) 0.0635(8) Uani 1 2 d S
N9 N 0.4309(4) 0.2500 -0.1578(2) 0.0958(12) Uani 1 2 d S
C3 C 0.8175(3) 0.2500 0.06571(16) 0.0452(7) Uani 1 2 d S
C2 C 0.6793(3) 0.2500 0.02112(15) 0.0419(7) Uani 1 2 d S
C1 C 0.6802(3) 0.2500 -0.07183(16) 0.0478(7) Uani 1 2 d S
C6 C 0.8138(4) 0.2500 -0.11922(19) 0.0638(9) Uani 1 2 d S
H6 H 0.8131 0.2500 -0.1822 0.077 Uiso 1 2 calc SR
C5 C 0.9463(3) 0.2500 -0.0737(2) 0.0689(10) Uani 1 2 d S
H5 H 1.0378 0.2500 -0.1059 0.083 Uiso 1 2 calc SR
C4 C 0.9515(3) 0.2500 0.0181(2) 0.0572(8) Uani 1 2 d S
C13 C 0.5344(3) 0.2500 0.07080(18) 0.0604(8) Uani 1 2 d S
H13A H 0.5073 0.3709 0.0863 0.091 Uiso 0.50 1 calc PR
H13B H 0.5453 0.1803 0.1250 0.091 Uiso 0.50 1 calc PR
H13C H 0.4556 0.1988 0.0336 0.091 Uiso 0.50 1 calc PR
C8 C 0.5403(4) 0.2500 -0.11888(19) 0.0651(9) Uani 1 2 d S
C12 C 1.1034(3) 0.2500 0.0633(3) 0.0870(12) Uani 1 2 d S
H12A H 1.1782 0.3021 0.0236 0.131 Uiso 0.50 1 calc PR
H12B H 1.1324 0.1290 0.0774 0.131 Uiso 0.50 1 calc PR
H12C H 1.0978 0.3189 0.1180 0.131 Uiso 0.50 1 calc PR
C10 C 0.8443(3) 0.0914(3) 0.20650(14) 0.0846(9) Uani 1 1 d .
H10A H 0.9534 0.0764 0.2092 0.127 Uiso 1 1 calc R
H10B H 0.7996 -0.0083 0.1750 0.127 Uiso 1 1 calc R
H10C H 0.8037 0.0970 0.2668 0.127 Uiso 1 1 calc R
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.001000
0 0 -1 0.070000
8 -1 0 0.078000
-1 0 0 0.050000
1 5 0 0.120000
-1 -6 0 0.181000
-4 -3 0 0.074000
-4 -1 0 0.043000
1 0 -3 0.082000
1 3 -7 0.111000
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C10 N7 C10 115.9(2) . 8_565
C10 N7 C3 118.31(14) . .
C10 N7 C3 118.31(14) 8_565 .
C4 C3 C2 120.4(2) . .
C4 C3 N7 123.8(2) . .
C2 C3 N7 115.9(2) . .
C1 C2 C3 118.3(2) . .
C1 C2 C13 120.4(2) . .
C3 C2 C13 121.2(2) . .
C6 C1 C2 121.3(2) . .
C6 C1 C8 119.4(2) . .
C2 C1 C8 119.3(2) . .
C5 C6 C1 118.8(3) . .
C5 C6 H6 120.6 . .
C1 C6 H6 120.6 . .
C6 C5 C4 122.1(3) . .
C6 C5 H5 118.9 . .
C4 C5 H5 118.9 . .
C5 C4 C3 119.1(3) . .
C5 C4 C12 118.6(3) . .
C3 C4 C12 122.3(3) . .
C2 C13 H13A 109.5 . .
C2 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C2 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
N9 C8 C1 178.6(4) . .
C4 C12 H12A 109.5 . .
C4 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C4 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
N7 C10 H10A 109.5 . .
N7 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
N7 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N7 C10 1.425(2) .
N7 C10 1.425(2) 8_565
N7 C3 1.435(3) .
N9 C8 1.139(4) .
C3 C4 1.394(4) .
C3 C2 1.404(3) .
C2 C1 1.402(3) .
C2 C13 1.494(3) .
C1 C6 1.390(4) .
C1 C8 1.435(4) .
C6 C5 1.367(4) .
C6 H6 0.9500 .
C5 C4 1.386(5) .
C5 H5 0.9500 .
C4 C12 1.516(4) .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
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_site_symmetry_1
C10 N7 C3 C4 -74.3(2) .
C10 N7 C3 C4 74.3(2) 8_565
C10 N7 C3 C2 105.7(2) .
C10 N7 C3 C2 -105.7(2) 8_565
C4 C3 C2 C1 0.0 .
N7 C3 C2 C1 180.0 .
C4 C3 C2 C13 180.0 .
N7 C3 C2 C13 0.0 .
C3 C2 C1 C6 0.0 .
C13 C2 C1 C6 180.0 .
C3 C2 C1 C8 180.0 .
C13 C2 C1 C8 0.0 .
C2 C1 C6 C5 0.0 .
C8 C1 C6 C5 180.0 .
C1 C6 C5 C4 0.0 .
C6 C5 C4 C3 0.0 .
C6 C5 C4 C12 180.0 .
C2 C3 C4 C5 0.0 .
N7 C3 C4 C5 180.0 .
C2 C3 C4 C12 180.0 .
N7 C3 C4 C12 0.0 .
loop_
_reflns_scale_group_code
_reflns_scale_meas_F
1 1.0
