#------------------------------------------------------------------------------
#$Date: 2016-02-16 21:30:59 +0100 (mar 16 de feb de 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/55/4025541.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_4025541
loop_
_publ_author_name
'H. M. Dhammika Bandara'
'Tracey R. Friss'
'Miriam M. Enriquez'
'William Isley'
'Christopher Incarvito'
'Harry A. Frank'
'Jose Gascon'
'Shawn C. Burdette'
_publ_section_title
;
 Proof for the Concerted Inversion Mechanism in the trans → cis
 Isomerization of Azobenzene Using Hydrogen Bonding To Induce Isomer
 Locking
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4817
_journal_page_last               4827
_journal_paper_doi               10.1021/jo100866m
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C24 H22 N6 '
_chemical_formula_sum            'C24 H22 N6'
_chemical_formula_weight         394.48
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.328(2)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   10.1401(11)
_cell_length_b                   13.6843(15)
_cell_length_c                   7.3008(8)
_cell_measurement_reflns_used    8805
_cell_measurement_temperature    223.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     1008.68(19)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  SHELXL
_computing_structure_solution    SHELXS97
_diffrn_detector_area_resol_mean 6.85
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10199
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             416.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2301
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0588P)²+0.1505P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1294
_reflns_number_gt                1784
_reflns_number_total             2301
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo100866m_si_002.cif
_cod_data_source_block           '_User-defined'
_cod_original_formula_sum        'C24 H22 N6 '
_cod_database_code               4025541
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
N(1) N 1.20763(11) 0.08282(9) 0.55555(17) 0.0495(3) Uani 1.00 1 d . . .
N(2) N 0.96962(12) 0.10546(9) 0.67655(17) 0.0461(3) Uani 1.00 1 d . . .
N(3) N 0.94420(10) 0.00372(8) 1.03370(15) 0.0440(3) Uani 1.00 1 d . . .
C(1) C 1.33237(15) 0.07706(12) 0.5099(2) 0.0573(4) Uani 1.00 1 d . . .
C(2) C 1.37671(16) 0.11910(12) 0.3570(2) 0.0604(4) Uani 1.00 1 d . . .
C(3) C 1.28670(17) 0.16929(13) 0.2408(2) 0.0671(4) Uani 1.00 1 d . . .
C(4) C 1.15765(16) 0.17602(12) 0.2838(2) 0.0603(4) Uani 1.00 1 d . . .
C(5) C 1.12136(13) 0.13266(9) 0.44274(19) 0.0424(3) Uani 1.00 1 d . . .
C(6) C 0.98048(13) 0.14112(10) 0.49250(19) 0.0457(3) Uani 1.00 1 d . . .
C(7) C 0.85633(12) 0.10841(9) 0.76188(18) 0.0407(3) Uani 1.00 1 d . . .
C(8) C 0.74392(14) 0.16025(11) 0.6859(2) 0.0493(3) Uani 1.00 1 d . . .
C(9) C 0.62891(14) 0.16324(12) 0.7718(2) 0.0547(4) Uani 1.00 1 d . . .
C(10) C 0.61831(15) 0.11495(12) 0.9366(2) 0.0576(4) Uani 1.00 1 d . . .
C(11) C 0.72696(14) 0.06454(11) 1.0153(2) 0.0516(3) Uani 1.00 1 d . . .
C(12) C 0.84582(12) 0.06039(10) 0.93354(18) 0.0416(3) Uani 1.00 1 d . . .
H(1) H 1.3937 0.0417 0.5884 0.069 Uiso 1.00 1 c R . .
H(2) H 1.4658 0.1138 0.3325 0.073 Uiso 1.00 1 c R . .
H(3) H 1.3127 0.1987 0.1335 0.081 Uiso 1.00 1 c R . .
H(4) H 1.0945 0.2099 0.2055 0.072 Uiso 1.00 1 c R . .
H(5) H 0.9525 0.2096 0.4843 0.055 Uiso 1.00 1 c R . .
H(6) H 0.9217 0.1033 0.4050 0.055 Uiso 1.00 1 c R . .
H(7) H 0.7478 0.1936 0.5739 0.059 Uiso 1.00 1 c R . .
H(8) H 0.5561 0.1987 0.7176 0.066 Uiso 1.00 1 c R . .
H(9) H 0.5389 0.1165 0.9935 0.069 Uiso 1.00 1 c R . .
H(10) H 0.7207 0.0319 1.1275 0.062 Uiso 1.00 1 c R . .
H(2A) H 1.0374(16) 0.0732(11) 0.725(2) 0.056(4) Uiso 1.00 1 c . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C(1) N(1) C(5) 117.21(13) yes . . .
C(6) N(2) C(7) 123.93(11) yes . . .
N(3) N(3) C(12) 116.87(10) yes 3_757 . .
N(1) C(1) C(2) 124.57(14) yes . . .
C(1) C(2) C(3) 117.71(15) yes . . .
C(2) C(3) C(4) 118.99(16) yes . . .
C(3) C(4) C(5) 119.66(14) yes . . .
N(1) C(5) C(4) 121.85(13) yes . . .
N(1) C(5) C(6) 118.15(12) yes . . .
C(4) C(5) C(6) 120.00(12) yes . . .
N(2) C(6) C(5) 110.70(10) yes . . .
N(2) C(7) C(8) 121.44(12) yes . . .
N(2) C(7) C(12) 121.64(11) yes . . .
C(8) C(7) C(12) 116.92(11) yes . . .
C(7) C(8) C(9) 121.61(13) yes . . .
C(8) C(9) C(10) 121.27(13) yes . . .
C(9) C(10) C(11) 118.47(14) yes . . .
C(10) C(11) C(12) 122.07(14) yes . . .
N(3) C(12) C(7) 126.89(11) yes . . .
N(3) C(12) C(11) 113.43(11) yes . . .
C(7) C(12) C(11) 119.65(11) yes . . .
C(6) N(2) H(2A) 115.3(11) no . . .
C(7) N(2) H(2A) 120.1(11) no . . .
N(1) C(1) H(1) 117.7 no . . .
C(2) C(1) H(1) 117.7 no . . .
C(1) C(2) H(2) 121.1 no . . .
C(3) C(2) H(2) 121.1 no . . .
C(2) C(3) H(3) 120.5 no . . .
C(4) C(3) H(3) 120.5 no . . .
C(3) C(4) H(4) 120.2 no . . .
C(5) C(4) H(4) 120.2 no . . .
N(2) C(6) H(5) 109.5 no . . .
N(2) C(6) H(6) 109.5 no . . .
C(5) C(6) H(5) 109.5 no . . .
C(5) C(6) H(6) 109.5 no . . .
H(5) C(6) H(6) 108.1 no . . .
C(7) C(8) H(7) 119.2 no . . .
C(9) C(8) H(7) 119.2 no . . .
C(8) C(9) H(8) 119.4 no . . .
C(10) C(9) H(8) 119.4 no . . .
C(9) C(10) H(9) 120.8 no . . .
C(11) C(10) H(9) 120.8 no . . .
C(10) C(11) H(10) 119.0 no . . .
C(12) C(11) H(10) 119.0 no . . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
N(1) C(1) 1.3399(19) yes . .
N(1) C(5) 1.3323(17) yes . .
N(2) C(6) 1.4434(18) yes . .
N(2) C(7) 1.3573(18) yes . .
N(3) N(3) 1.2793(15) yes . 3_757
N(3) C(12) 1.4127(16) yes . .
C(1) C(2) 1.368(2) yes . .
C(2) C(3) 1.371(2) yes . .
C(3) C(4) 1.377(2) yes . .
C(4) C(5) 1.383(2) yes . .
C(5) C(6) 1.5108(19) yes . .
C(7) C(8) 1.4116(18) yes . .
C(7) C(12) 1.4278(18) yes . .
C(8) C(9) 1.375(2) yes . .
C(9) C(10) 1.386(2) yes . .
C(10) C(11) 1.379(2) yes . .
C(11) C(12) 1.3948(19) yes . .
N(2) H(2A) 0.865(15) no . .
C(1) H(1) 0.940 no . .
C(2) H(2) 0.940 no . .
C(3) H(3) 0.940 no . .
C(4) H(4) 0.940 no . .
C(6) H(5) 0.980 no . .
C(6) H(6) 0.980 no . .
C(8) H(7) 0.940 no . .
C(9) H(8) 0.940 no . .
C(10) H(9) 0.940 no . .
C(11) H(10) 0.940 no . .
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
N(1) N(2) 3.4892(16) ? . 3_756
N(1) C(7) 3.5157(17) ? . 3_756
N(2) N(1) 3.4892(16) ? . 3_756
N(2) C(4) 3.593(2) ? . 4_555
N(2) C(5) 3.4754(17) ? . 3_756
N(3) C(4) 3.5837(19) ? . 1_556
N(3) C(4) 3.4704(19) ? . 3_756
C(4) N(2) 3.593(2) ? . 4_554
C(4) N(3) 3.5837(19) ? . 1_554
C(4) N(3) 3.4704(19) ? . 3_756
C(5) N(2) 3.4754(17) ? . 3_756
C(7) N(1) 3.5157(17) ? . 3_756
N(1) H(3) 3.208 ? . 4_555
N(1) H(4) 3.285 ? . 4_555
N(1) H(6) 2.891 ? . 3_756
N(2) H(4) 2.825 ? . 4_555
N(2) H(5) 3.399 ? . 4_555
N(2) H(6) 3.138 ? . 3_756
N(3) H(4) 3.391 ? . 1_556
N(3) H(4) 3.409 ? . 3_756
N(3) H(6) 3.061 ? . 1_556
C(1) H(1) 3.353 ? . 3_856
C(1) H(2) 3.449 ? . 3_856
C(1) H(3) 3.210 ? . 4_555
C(1) H(8) 3.095 ? . 1_655
C(2) H(1) 3.201 ? . 3_856
C(2) H(3) 3.310 ? . 4_555
C(2) H(8) 3.246 ? . 1_655
C(2) H(8) 3.302 ? . 4_654
C(2) H(9) 3.250 ? . 1_654
C(3) H(3) 3.378 ? . 4_555
C(3) H(8) 3.292 ? . 4_654
C(3) H(9) 3.343 ? . 1_654
C(4) H(3) 3.345 ? . 4_555
C(4) H(4) 3.563 ? . 4_555
C(4) H(5) 3.273 ? . 4_554
C(5) H(3) 3.245 ? . 4_555
C(5) H(4) 2.914 ? . 4_555
C(5) H(6) 3.455 ? . 3_756
C(5) H(2A) 3.414(15) ? . 3_756
C(6) H(4) 2.753 ? . 4_555
C(6) H(6) 3.548 ? . 3_756
C(6) H(2A) 3.332(15) ? . 3_756
C(7) H(4) 3.517 ? . 4_555
C(7) H(5) 3.081 ? . 4_555
C(8) H(5) 3.396 ? . 4_555
C(8) H(7) 3.465 ? . 4_555
C(9) H(1) 3.107 ? . 1_455
C(9) H(2) 3.535 ? . 1_455
C(9) H(2) 3.518 ? . 4_455
C(9) H(7) 3.109 ? . 4_555
C(10) H(1) 3.403 ? . 1_455
C(10) H(2) 3.402 ? . 1_456
C(10) H(7) 3.058 ? . 4_555
C(10) H(8) 3.369 ? . 4_555
C(11) H(6) 3.352 ? . 1_556
C(11) H(7) 3.342 ? . 4_555
C(12) H(5) 3.337 ? . 4_555
C(12) H(6) 3.506 ? . 1_556
H(1) C(1) 3.353 ? . 3_856
H(1) C(2) 3.201 ? . 3_856
H(1) C(9) 3.107 ? . 1_655
H(1) C(10) 3.403 ? . 1_655
H(1) H(1) 2.851 ? . 3_856
H(1) H(2) 2.595 ? . 3_856
H(1) H(8) 2.816 ? . 1_655
H(1) H(9) 3.340 ? . 1_655
H(2) C(1) 3.449 ? . 3_856
H(2) C(9) 3.535 ? . 1_655
H(2) C(9) 3.518 ? . 4_654
H(2) C(10) 3.402 ? . 1_654
H(2) H(1) 2.595 ? . 3_856
H(2) H(7) 3.397 ? . 1_655
H(2) H(8) 3.101 ? . 1_655
H(2) H(8) 2.875 ? . 4_654
H(2) H(9) 2.649 ? . 1_654
H(2) H(10) 3.301 ? . 1_654
H(3) N(1) 3.208 ? . 4_554
H(3) C(1) 3.210 ? . 4_554
H(3) C(2) 3.310 ? . 4_554
H(3) C(3) 3.378 ? . 4_554
H(3) C(4) 3.345 ? . 4_554
H(3) C(5) 3.245 ? . 4_554
H(3) H(8) 2.856 ? . 4_654
H(3) H(9) 2.829 ? . 1_654
H(4) N(1) 3.285 ? . 4_554
H(4) N(2) 2.825 ? . 4_554
H(4) N(3) 3.391 ? . 1_554
H(4) N(3) 3.409 ? . 3_756
H(4) C(4) 3.563 ? . 4_554
H(4) C(5) 2.914 ? . 4_554
H(4) C(6) 2.753 ? . 4_554
H(4) C(7) 3.517 ? . 4_554
H(4) H(5) 2.338 ? . 4_554
H(4) H(2A) 3.031 ? . 4_554
H(5) N(2) 3.399 ? . 4_554
H(5) C(4) 3.273 ? . 4_555
H(5) C(7) 3.081 ? . 4_554
H(5) C(8) 3.396 ? . 4_554
H(5) C(12) 3.337 ? . 4_554
H(5) H(4) 2.338 ? . 4_555
H(6) N(1) 2.891 ? . 3_756
H(6) N(2) 3.138 ? . 3_756
H(6) N(3) 3.061 ? . 1_554
H(6) C(5) 3.455 ? . 3_756
H(6) C(6) 3.548 ? . 3_756
H(6) C(11) 3.352 ? . 1_554
H(6) C(12) 3.506 ? . 1_554
H(6) H(6) 3.467 ? . 3_756
H(6) H(10) 2.906 ? . 1_554
H(6) H(2A) 2.641 ? . 3_756
H(7) C(8) 3.465 ? . 4_554
H(7) C(9) 3.109 ? . 4_554
H(7) C(10) 3.058 ? . 4_554
H(7) C(11) 3.342 ? . 4_554
H(7) H(2) 3.397 ? . 1_455
H(7) H(8) 3.433 ? . 4_554
H(7) H(9) 3.370 ? . 4_554
H(8) C(1) 3.095 ? . 1_455
H(8) C(2) 3.246 ? . 1_455
H(8) C(2) 3.302 ? . 4_455
H(8) C(3) 3.292 ? . 4_455
H(8) C(10) 3.369 ? . 4_554
H(8) H(1) 2.816 ? . 1_455
H(8) H(2) 3.101 ? . 1_455
H(8) H(2) 2.875 ? . 4_455
H(8) H(3) 2.856 ? . 4_455
H(8) H(7) 3.433 ? . 4_555
H(8) H(9) 3.008 ? . 4_554
H(9) C(2) 3.250 ? . 1_456
H(9) C(3) 3.343 ? . 1_456
H(9) H(1) 3.340 ? . 1_455
H(9) H(2) 2.649 ? . 1_456
H(9) H(3) 2.829 ? . 1_456
H(9) H(7) 3.370 ? . 4_555
H(9) H(8) 3.008 ? . 4_555
H(9) H(9) 3.289 ? . 3_657
H(9) H(10) 3.377 ? . 3_657
H(10) H(2) 3.301 ? . 1_456
H(10) H(6) 2.906 ? . 1_556
H(10) H(9) 3.377 ? . 3_657
H(2A) C(5) 3.414(15) ? . 3_756
H(2A) C(6) 3.332(15) ? . 3_756
H(2A) H(4) 3.031 ? . 4_555
H(2A) H(6) 2.641 ? . 3_756
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C(1) N(1) C(5) C(4) 0.7(2) ? . . . .
C(1) N(1) C(5) C(6) -179.32(12) ? . . . .
C(5) N(1) C(1) C(2) 0.4(2) ? . . . .
C(6) N(2) C(7) C(8) -9.5(2) ? . . . .
C(6) N(2) C(7) C(12) 171.33(12) ? . . . .
C(7) N(2) C(6) C(5) 176.63(11) ? . . . .
N(3) N(3) C(12) C(7) 1.78(19) ? 3_757 . . .
N(3) N(3) C(12) C(11) 179.67(11) ? 3_757 . . .
N(1) C(1) C(2) C(3) -1.1(2) ? . . . .
C(1) C(2) C(3) C(4) 0.7(2) ? . . . .
C(2) C(3) C(4) C(5) 0.3(2) ? . . . .
C(3) C(4) C(5) N(1) -1.0(2) ? . . . .
C(3) C(4) C(5) C(6) 178.99(14) ? . . . .
N(1) C(5) C(6) N(2) 9.72(16) ? . . . .
C(4) C(5) C(6) N(2) -170.29(12) ? . . . .
N(2) C(7) C(8) C(9) 179.86(13) ? . . . .
N(2) C(7) C(12) N(3) -1.6(2) ? . . . .
N(2) C(7) C(12) C(11) -179.33(12) ? . . . .
C(8) C(7) C(12) N(3) 179.24(12) ? . . . .
C(8) C(7) C(12) C(11) 1.47(18) ? . . . .
C(12) C(7) C(8) C(9) -0.9(2) ? . . . .
C(7) C(8) C(9) C(10) -0.3(2) ? . . . .
C(8) C(9) C(10) C(11) 1.0(2) ? . . . .
C(9) C(10) C(11) C(12) -0.4(2) ? . . . .
C(10) C(11) C(12) N(3) -178.89(13) ? . . . .
C(10) C(11) C(12) C(7) -0.8(2) ? . . . .
