#------------------------------------------------------------------------------
#$Date: 2019-09-25 11:50:40 +0300 (Wed, 25 Sep 2019) $
#$Revision: 218820 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/41/7234138.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_7234138
loop_
_publ_author_name
'Pachaiyappan Rajamalli'
'Parthasarathy Gandeepan'
'Min-Jie Huang'
'Chien-Hong Cheng'
_publ_section_title
;
 Bromo induced reversible distinct color switching of a structurally
 simple donor-acceptor molecule by vapo, piezo and thermal stimuli
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              3329
_journal_page_last               3335
_journal_paper_doi               10.1039/C5TC00109A
_journal_volume                  3
_journal_year                    2015
_chemical_formula_sum            'C29 H24 Br Cl2 N'
_chemical_formula_weight         537.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.2686(9)
_cell_length_b                   12.6470(9)
_cell_length_c                   31.172(2)
_cell_measurement_reflns_used    5452
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.6317
_cell_measurement_theta_min      2.6136
_cell_volume                     4836.7(6)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            36389
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.418
_diffrn_reflns_theta_min         2.113
_exptl_absorpt_coefficient_mu    1.939
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.7603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lamellar
_exptl_crystal_F_000             2192
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.01
_refine_diff_density_max         3.383
_refine_diff_density_min         -1.497
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4966
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0657
_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)+(0.0510P)²+36.6274P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1501
_refine_ls_wR_factor_ref         0.1609
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3781
_reflns_number_total             4966
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            J-Mater-Chem-C-2015-3-3329.cif
_cod_data_source_block           mo_140632lt_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               7234138
_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           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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
Br1 Br 0.64563(4) 0.24163(4) 0.33255(2) 0.02227(16) Uani 1 1 d . . . . .
C1 C 0.6321(4) 0.2302(3) 0.27221(14) 0.0127(9) Uani 1 1 d . . . . .
C2 C 0.5433(4) 0.1736(3) 0.25497(15) 0.0126(9) Uani 1 1 d . . . . .
C3 C 0.4635(4) 0.1207(4) 0.28042(16) 0.0163(10) Uani 1 1 d . . . . .
H3 H 0.4676 0.1249 0.3108 0.020 Uiso 1 1 calc R U . . .
C4 C 0.3814(4) 0.0641(4) 0.26187(17) 0.0182(11) Uani 1 1 d . . . . .
H4 H 0.3295 0.0290 0.2794 0.022 Uiso 1 1 calc R U . . .
C5 C 0.3727(4) 0.0573(4) 0.21652(17) 0.0175(10) Uani 1 1 d . . . . .
H5 H 0.3157 0.0170 0.2039 0.021 Uiso 1 1 calc R U . . .
C6 C 0.4456(4) 0.1083(3) 0.19107(16) 0.0139(9) Uani 1 1 d . . . . .
H6 H 0.4385 0.1039 0.1608 0.017 Uiso 1 1 calc R U . . .
C7 C 0.5334(4) 0.1689(3) 0.20921(15) 0.0120(9) Uani 1 1 d . . . . .
C8 C 0.6070(4) 0.2244(3) 0.18295(15) 0.0126(9) Uani 1 1 d . . . . .
C9 C 0.6964(4) 0.2781(3) 0.20058(16) 0.0138(9) Uani 1 1 d . . . . .
C10 C 0.7741(4) 0.3319(4) 0.17427(17) 0.0163(10) Uani 1 1 d . . . . .
H10 H 0.7650 0.3323 0.1440 0.020 Uiso 1 1 calc R U . . .
C11 C 0.8613(4) 0.3825(4) 0.19206(18) 0.0217(11) Uani 1 1 d . . . . .
H11 H 0.9126 0.4172 0.1741 0.026 Uiso 1 1 calc R U . . .
C12 C 0.8755(4) 0.3836(4) 0.23676(18) 0.0213(11) Uani 1 1 d . . . . .
H12 H 0.9367 0.4192 0.2486 0.026 Uiso 1 1 calc R U . . .
C13 C 0.8035(4) 0.3349(4) 0.26341(17) 0.0177(10) Uani 1 1 d . . . . .
H13 H 0.8150 0.3367 0.2935 0.021 Uiso 1 1 calc R U . . .
C14 C 0.7106(4) 0.2808(3) 0.24634(16) 0.0139(9) Uani 1 1 d . . . . .
C15 C 0.4976(4) 0.2903(4) 0.12370(16) 0.0150(10) Uani 1 1 d . . . . .
C16 C 0.4773(4) 0.3865(4) 0.14380(16) 0.0149(10) Uani 1 1 d . . . . .
H16 H 0.5244 0.4105 0.1659 0.018 Uiso 1 1 calc R U . . .
C17 C 0.3887(4) 0.4474(4) 0.13173(17) 0.0199(11) Uani 1 1 d . . . . .
H17 H 0.3770 0.5136 0.1454 0.024 Uiso 1 1 calc R U . . .
C18 C 0.3163(4) 0.4143(4) 0.10005(17) 0.0203(11) Uani 1 1 d . . . . .
C19 C 0.3369(4) 0.3170(4) 0.08085(16) 0.0213(11) Uani 1 1 d . . . . .
H19 H 0.2885 0.2920 0.0593 0.026 Uiso 1 1 calc R U . . .
C20 C 0.4261(4) 0.2552(4) 0.09220(15) 0.0193(10) Uani 1 1 d . . . . .
H20 H 0.4382 0.1892 0.0784 0.023 Uiso 1 1 calc R U . . .
C21 C 0.2178(4) 0.4804(5) 0.08849(19) 0.0308(13) Uani 1 1 d . . . . .
H21A H 0.1582 0.4647 0.1084 0.046 Uiso 1 1 calc R U . . .
H21B H 0.1948 0.4637 0.0591 0.046 Uiso 1 1 calc R U . . .
H21C H 0.2366 0.5555 0.0904 0.046 Uiso 1 1 calc R U . . .
C22 C 0.6548(4) 0.1716(4) 0.10891(16) 0.0169(10) Uani 1 1 d . . . . .
C23 C 0.6567(4) 0.1934(4) 0.06512(16) 0.0202(10) Uani 1 1 d . . . . .
H23 H 0.6126 0.2486 0.0539 0.024 Uiso 1 1 calc R U . . .
C24 C 0.7220(4) 0.1356(4) 0.03799(18) 0.0250(12) Uani 1 1 d . . . . .
H24 H 0.7199 0.1507 0.0082 0.030 Uiso 1 1 calc R U . . .
C25 C 0.7910(4) 0.0559(4) 0.05246(17) 0.0214(11) Uani 1 1 d . . . . .
C26 C 0.7907(4) 0.0361(4) 0.09651(17) 0.0218(11) Uani 1 1 d . . . . .
H26 H 0.8372 -0.0171 0.1078 0.026 Uiso 1 1 calc R U . . .
C27 C 0.7236(4) 0.0927(4) 0.12428(17) 0.0193(10) Uani 1 1 d . . . . .
H27 H 0.7248 0.0772 0.1541 0.023 Uiso 1 1 calc R U . . .
C28 C 0.8584(5) -0.0097(5) 0.02234(18) 0.0290(12) Uani 1 1 d . . . . .
H28A H 0.8161 -0.0713 0.0130 0.044 Uiso 1 1 calc R U . . .
H28B H 0.9246 -0.0335 0.0370 0.044 Uiso 1 1 calc R U . . .
H28C H 0.8785 0.0329 -0.0027 0.044 Uiso 1 1 calc R U . . .
C29 C 0.9524(6) 0.2896(6) 0.0713(2) 0.0504(19) Uani 1 1 d . . . . .
H29A H 0.9717 0.3213 0.0993 0.060 Uiso 1 1 calc R U . . .
H29B H 0.8821 0.2520 0.0746 0.060 Uiso 1 1 calc R U . . .
Cl1 Cl 1.05394(13) 0.19979(14) 0.05575(6) 0.0426(4) Uani 1 1 d . . . . .
Cl2 Cl 0.9392(2) 0.3895(2) 0.03257(14) 0.1179(13) Uani 1 1 d . . . . .
N1 N 0.5876(3) 0.2279(3) 0.13765(12) 0.0132(8) 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'
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'
Br Br -0.2901 2.4595 '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'
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
C14 C1 C2 122.7(4) . .
C14 C1 Br1 118.3(3) . .
C2 C1 Br1 119.0(3) . .
C1 C2 C3 123.8(4) . .
C1 C2 C7 117.8(4) . .
C3 C2 C7 118.4(4) . .
C4 C3 C2 121.1(5) . .
C4 C3 H3 119.4 . .
C2 C3 H3 119.4 . .
C3 C4 C5 120.6(4) . .
C3 C4 H4 119.7 . .
C5 C4 H4 119.7 . .
C6 C5 C4 120.2(4) . .
C6 C5 H5 119.9 . .
C4 C5 H5 119.9 . .
C5 C6 C7 121.1(5) . .
C5 C6 H6 119.4 . .
C7 C6 H6 119.4 . .
C8 C7 C2 120.3(4) . .
C8 C7 C6 121.2(4) . .
C2 C7 C6 118.5(4) . .
C9 C8 C7 121.1(4) . .
C9 C8 N1 120.1(4) . .
C7 C8 N1 118.9(4) . .
C8 C9 C10 121.8(4) . .
C8 C9 C14 119.7(4) . .
C10 C9 C14 118.5(4) . .
C11 C10 C9 120.9(5) . .
C11 C10 H10 119.6 . .
C9 C10 H10 119.6 . .
C10 C11 C12 120.4(5) . .
C10 C11 H11 119.8 . .
C12 C11 H11 119.8 . .
C13 C12 C11 121.4(5) . .
C13 C12 H12 119.3 . .
C11 C12 H12 119.3 . .
C12 C13 C14 120.4(5) . .
C12 C13 H13 119.8 . .
C14 C13 H13 119.8 . .
C1 C14 C13 123.2(5) . .
C1 C14 C9 118.3(4) . .
C13 C14 C9 118.4(4) . .
C20 C15 C16 119.0(4) . .
C20 C15 N1 121.9(4) . .
C16 C15 N1 119.0(4) . .
C17 C16 C15 120.3(5) . .
C17 C16 H16 119.8 . .
C15 C16 H16 119.8 . .
C16 C17 C18 121.7(5) . .
C16 C17 H17 119.1 . .
C18 C17 H17 119.1 . .
C19 C18 C17 117.1(5) . .
C19 C18 C21 122.1(5) . .
C17 C18 C21 120.8(5) . .
C20 C19 C18 122.0(5) . .
C20 C19 H19 119.0 . .
C18 C19 H19 119.0 . .
C15 C20 C19 119.8(5) . .
C15 C20 H20 120.1 . .
C19 C20 H20 120.1 . .
C18 C21 H21A 109.5 . .
C18 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C18 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C27 C22 C23 118.0(4) . .
C27 C22 N1 119.8(4) . .
C23 C22 N1 122.2(4) . .
C24 C23 C22 120.5(5) . .
C24 C23 H23 119.8 . .
C22 C23 H23 119.8 . .
C23 C24 C25 122.7(5) . .
C23 C24 H24 118.7 . .
C25 C24 H24 118.7 . .
C24 C25 C26 116.5(5) . .
C24 C25 C28 122.2(5) . .
C26 C25 C28 121.2(5) . .
C27 C26 C25 121.4(5) . .
C27 C26 H26 119.3 . .
C25 C26 H26 119.3 . .
C26 C27 C22 120.9(5) . .
C26 C27 H27 119.6 . .
C22 C27 H27 119.6 . .
C25 C28 H28A 109.5 . .
C25 C28 H28B 109.5 . .
H28A C28 H28B 109.5 . .
C25 C28 H28C 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
Cl1 C29 Cl2 109.9(4) . .
Cl1 C29 H29A 109.7 . .
Cl2 C29 H29A 109.7 . .
Cl1 C29 H29B 109.7 . .
Cl2 C29 H29B 109.7 . .
H29A C29 H29B 108.2 . .
C22 N1 C15 122.6(4) . .
C22 N1 C8 120.9(4) . .
C15 N1 C8 116.5(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.894(5) .
C1 C14 1.409(7) .
C1 C2 1.410(6) .
C2 C3 1.428(6) .
C2 C7 1.433(7) .
C3 C4 1.364(7) .
C3 H3 0.9500 .
C4 C5 1.420(7) .
C4 H4 0.9500 .
C5 C6 1.359(7) .
C5 H5 0.9500 .
C6 C7 1.437(6) .
C6 H6 0.9500 .
C7 C8 1.406(6) .
C8 C9 1.402(6) .
C8 N1 1.433(6) .
C9 C10 1.430(7) .
C9 C14 1.437(7) .
C10 C11 1.364(7) .
C10 H10 0.9500 .
C11 C12 1.404(8) .
C11 H11 0.9500 .
C12 C13 1.360(7) .
C12 H12 0.9500 .
C13 C14 1.432(6) .
C13 H13 0.9500 .
C15 C20 1.389(7) .
C15 C16 1.391(7) .
C15 N1 1.426(6) .
C16 C17 1.384(7) .
C16 H16 0.9500 .
C17 C18 1.393(7) .
C17 H17 0.9500 .
C18 C19 1.391(7) .
C18 C21 1.513(7) .
C19 C20 1.391(7) .
C19 H19 0.9500 .
C20 H20 0.9500 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 C27 1.392(7) .
C22 C23 1.393(7) .
C22 N1 1.410(6) .
C23 C24 1.375(7) .
C23 H23 0.9500 .
C24 C25 1.392(7) .
C24 H24 0.9500 .
C25 C26 1.396(8) .
C25 C28 1.501(7) .
C26 C27 1.392(7) .
C26 H26 0.9500 .
C27 H27 0.9500 .
C28 H28A 0.9800 .
C28 H28B 0.9800 .
C28 H28C 0.9800 .
C29 Cl1 1.755(7) .
C29 Cl2 1.756(9) .
C29 H29A 0.9900 .
C29 H29B 0.9900 .
