#------------------------------------------------------------------------------
#$Date: 2020-03-26 01:37:56 +0200 (Thu, 26 Mar 2020) $
#$Revision: 249708 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/45/4134541.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_4134541
loop_
_publ_author_name
'Konrad, David B.'
'Savasci, Gökcen'
'Allmendinger, Lars'
'Trauner, Dirk'
'Ochsenfeld, Christian'
'Ali, Ahmed M.'
_publ_section_title
;
 Computational Design and Synthesis of a Deeply Red-Shifted and Bistable
 Azobenzene
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b10430
_journal_year                    2020
_chemical_formula_moiety         'C12 H6 Cl4 N2'
_chemical_formula_sum            'C12 H6 Cl4 N2'
_chemical_formula_weight         319.99
_chemical_name_common            621-cis
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_block_code                C12H6Cl4N2_wo055_trauner
_audit_creation_date             2018-07-04
_audit_creation_method           SHELXL-2014
_audit_update_record             05-Jul-18
_cell_angle_alpha                90
_cell_angle_beta                 107.709(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9223(6)
_cell_length_b                   7.4039(4)
_cell_length_c                   16.2847(9)
_cell_measurement_reflns_used    2032
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      28.1130
_cell_measurement_theta_min      4.6170
_cell_volume                     1254.50(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_refinement
;
Sheldrick, G. M. (2008).
Acta Cryst. A64, 112--122.
;
_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      143(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -12.00  93.00   1.00    8.00    --   21.54  77.00-150.00  105
  2  ω    -12.00  94.00   1.00    8.00    --   21.54  77.00  90.00  106
  3  ω    -11.00  94.00   1.00    8.00    --   21.54  77.00 -30.00  105
;
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Oxford XCalibur'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0592420000
_diffrn_orient_matrix_UB_12      0.0261185000
_diffrn_orient_matrix_UB_13      0.0058835000
_diffrn_orient_matrix_UB_21      0.0210342000
_diffrn_orient_matrix_UB_22      -0.0338207000
_diffrn_orient_matrix_UB_23      0.0427763000
_diffrn_orient_matrix_UB_31      0.0263358000
_diffrn_orient_matrix_UB_32      0.0857454000
_diffrn_orient_matrix_UB_33      0.0150540000
_diffrn_radiation_collimation    '0.5 mm collimator'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7186
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         28.718
_diffrn_reflns_theta_min         4.632
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           40_mA
_diffrn_source_power             2.00_kW
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50_kV
_exptl_absorpt_coefficient_mu    0.922
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_description       rod
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.458
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.096
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0335P)²+0.4113P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0913
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2293
_reflns_number_total             2908
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b10430_si_003.cif
_cod_data_source_block           wo055
_cod_original_cell_volume        1254.50(12)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4134541
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3651(2) 0.3605(3) 0.40361(14) 0.0208(5) Uani 1 1 d . . . . .
C2 C 0.3983(2) 0.2769(3) 0.48406(15) 0.0231(5) Uani 1 1 d . . . . .
C3 C 0.5212(2) 0.2127(3) 0.52281(16) 0.0303(6) Uani 1 1 d . . . . .
H3 H 0.5425 0.1575 0.5780 0.036 Uiso 1 1 calc R U . . .
C4 C 0.6131(2) 0.2294(3) 0.48062(17) 0.0321(6) Uani 1 1 d . . . . .
H4 H 0.6967 0.1815 0.5061 0.038 Uiso 1 1 calc R U . . .
C5 C 0.5842(2) 0.3156(3) 0.40144(16) 0.0289(6) Uani 1 1 d . . . . .
H5 H 0.6475 0.3274 0.3727 0.035 Uiso 1 1 calc R U . . .
C6 C 0.4627(2) 0.3836(3) 0.36510(15) 0.0252(5) Uani 1 1 d . . . . .
C7 C 0.1159(2) 0.1914(3) 0.34888(14) 0.0196(5) Uani 1 1 d . . . . .
C8 C 0.0186(2) 0.1463(3) 0.38464(14) 0.0228(5) Uani 1 1 d . . . . .
C9 C -0.0185(2) -0.0298(3) 0.39026(15) 0.0275(5) Uani 1 1 d . . . . .
H9 H -0.0838 -0.0571 0.4157 0.033 Uiso 1 1 calc R U . . .
C10 C 0.0407(2) -0.1670(3) 0.35824(15) 0.0304(6) Uani 1 1 d . . . . .
H10 H 0.0183 -0.2893 0.3640 0.036 Uiso 1 1 calc R U . . .
C11 C 0.1311(2) -0.1274(3) 0.31847(15) 0.0279(5) Uani 1 1 d . . . . .
H11 H 0.1694 -0.2216 0.2951 0.033 Uiso 1 1 calc R U . . .
C12 C 0.1668(2) 0.0500(3) 0.31228(14) 0.0220(5) Uani 1 1 d . . . . .
N1 N 0.24673(18) 0.4538(3) 0.36384(12) 0.0231(4) Uani 1 1 d . . . . .
N2 N 0.13797(18) 0.3818(3) 0.34176(12) 0.0222(4) Uani 1 1 d . . . . .
Cl1 Cl 0.28713(6) 0.26304(9) 0.54090(4) 0.03149(17) Uani 1 1 d . . . . .
Cl2 Cl 0.42788(6) 0.50185(9) 0.26893(4) 0.03718(18) Uani 1 1 d . . . . .
Cl3 Cl -0.05457(6) 0.31846(9) 0.42516(4) 0.03135(17) Uani 1 1 d . . . . .
Cl4 Cl 0.26952(6) 0.09475(9) 0.25197(4) 0.03240(17) Uani 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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 117.3(2) . . ?
C2 C1 N1 125.4(2) . . ?
C6 C1 N1 116.3(2) . . ?
C3 C2 C1 121.4(2) . . ?
C3 C2 Cl1 118.36(19) . . ?
C1 C2 Cl1 120.17(18) . . ?
C2 C3 C4 119.5(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 119.1(2) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 121.9(2) . . ?
C5 C6 Cl2 119.47(19) . . ?
C1 C6 Cl2 118.60(18) . . ?
C8 C7 C12 116.7(2) . . ?
C8 C7 N2 115.73(19) . . ?
C12 C7 N2 126.8(2) . . ?
C9 C8 C7 122.0(2) . . ?
C9 C8 Cl3 119.38(18) . . ?
C7 C8 Cl3 118.58(18) . . ?
C8 C9 C10 119.2(2) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 119.9(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C7 121.5(2) . . ?
C11 C12 Cl4 117.90(18) . . ?
C7 C12 Cl4 120.52(17) . . ?
N2 N1 C1 124.84(19) . . ?
N1 N2 C7 124.15(19) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.393(3) . ?
C1 C6 1.402(3) . ?
C1 N1 1.435(3) . ?
C2 C3 1.383(3) . ?
C2 Cl1 1.739(2) . ?
C3 C4 1.383(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.374(3) . ?
C5 H5 0.9500 . ?
C6 Cl2 1.732(2) . ?
C7 C8 1.398(3) . ?
C7 C12 1.400(3) . ?
C7 N2 1.441(3) . ?
C8 C9 1.376(3) . ?
C8 Cl3 1.738(2) . ?
C9 C10 1.388(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.367(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(3) . ?
C11 H11 0.9500 . ?
C12 Cl4 1.733(2) . ?
N1 N2 1.251(3) . ?
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -2.6(3) . . . . ?
N1 C1 C2 C3 -170.6(2) . . . . ?
C6 C1 C2 Cl1 173.66(17) . . . . ?
N1 C1 C2 Cl1 5.7(3) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
Cl1 C2 C3 C4 -177.13(18) . . . . ?
C2 C3 C4 C5 2.3(4) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C4 C5 C6 C1 -3.3(4) . . . . ?
C4 C5 C6 Cl2 176.64(18) . . . . ?
C2 C1 C6 C5 4.7(3) . . . . ?
N1 C1 C6 C5 173.8(2) . . . . ?
C2 C1 C6 Cl2 -175.26(17) . . . . ?
N1 C1 C6 Cl2 -6.2(3) . . . . ?
C12 C7 C8 C9 5.2(3) . . . . ?
N2 C7 C8 C9 175.7(2) . . . . ?
C12 C7 C8 Cl3 -176.22(16) . . . . ?
N2 C7 C8 Cl3 -5.7(3) . . . . ?
C7 C8 C9 C10 -1.1(3) . . . . ?
Cl3 C8 C9 C10 -179.65(18) . . . . ?
C8 C9 C10 C11 -2.6(3) . . . . ?
C9 C10 C11 C12 1.9(3) . . . . ?
C10 C11 C12 C7 2.5(3) . . . . ?
C10 C11 C12 Cl4 -173.66(18) . . . . ?
C8 C7 C12 C11 -5.9(3) . . . . ?
N2 C7 C12 C11 -175.2(2) . . . . ?
C8 C7 C12 Cl4 170.15(16) . . . . ?
N2 C7 C12 Cl4 0.8(3) . . . . ?
C2 C1 N1 N2 -63.6(3) . . . . ?
C6 C1 N1 N2 128.2(2) . . . . ?
C1 N1 N2 C7 -3.5(3) . . . . ?
C8 C7 N2 N1 133.5(2) . . . . ?
C12 C7 N2 N1 -57.0(3) . . . . ?
