#------------------------------------------------------------------------------
#$Date: 2019-11-24 16:41:40 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238611 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/77/7237794.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_7237794
loop_
_publ_author_name
'Sharber, Seth A.'
'Mann, Arielle'
'Shih, Kuo-Chih'
'Mullin, William J.'
'Nieh, Mu-Ping'
'Thomas, Samuel W.'
_publ_section_title
;
 Directed polymorphism and mechanofluorochromism of conjugated materials
 through weak non-covalent control
;
_journal_issue                   27
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              8316
_journal_paper_doi               10.1039/C9TC01301F
_journal_volume                  7
_journal_year                    2019
_chemical_formula_sum            'C44 H22 Cl6 F10 O8'
_chemical_formula_weight         1081.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2019-02-13 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.6230(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.5910(6)
_cell_length_b                   5.8584(2)
_cell_length_c                   26.0228(11)
_cell_measurement_reflns_used    8131
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      19.39
_cell_measurement_theta_min      2.85
_cell_volume                     2178.81(15)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0826
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            39436
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.357
_diffrn_reflns_theta_min         2.850
_exptl_absorpt_coefficient_mu    0.492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany'
_exptl_crystal_colour            Green
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1084
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane/hexanes'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   0.7444
_exptl_transmission_factor_min   0.7007
_refine_diff_density_max         1.455
_refine_diff_density_min         -0.976
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         3980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0448
_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)+(0.0396P)²+4.2276P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1066
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2970
_reflns_number_total             3980
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9tc01301f3.cif
_cod_data_source_block           SS190115_0m_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7237794
_shelx_shelxl_version_number     2017/1
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Cl1 Cl 0.71596(6) 0.20573(15) 0.39575(3) 0.0299(2) Uani 1 1 d . .
C1 C -0.03599(19) 1.0033(5) 0.54492(10) 0.0139(6) Uani 1 1 d . .
H1 H -0.060644 1.006384 0.576033 0.017 Uiso 1 1 calc R U
C2 C 0.02421(18) 0.8284(5) 0.53811(10) 0.0121(6) Uani 1 1 d . .
Cl2 Cl 0.70137(6) 0.17055(15) 0.28369(3) 0.0276(2) Uani 1 1 d . .
Cl3 Cl 0.70917(8) -0.23784(16) 0.34606(4) 0.0465(3) Uani 1 1 d . .
C3 C 0.06180(19) 0.8244(5) 0.49235(10) 0.0140(6) Uani 1 1 d . .
C21 C 0.04897(19) 0.6472(5) 0.57879(10) 0.0142(6) Uani 1 1 d . .
O21 O 0.09509(14) 0.4812(4) 0.57555(7) 0.0191(5) Uani 1 1 d . .
C22 C 0.0356(2) 0.5289(5) 0.66312(11) 0.0208(7) Uani 1 1 d . .
H22A H 0.103964 0.529315 0.677138 0.025 Uiso 1 1 calc R U
H22B H 0.016502 0.373380 0.650406 0.025 Uiso 1 1 calc R U
O22 O 0.01138(14) 0.6936(3) 0.62112(7) 0.0185(5) Uani 1 1 d . .
C23 C -0.0162(2) 0.6012(5) 0.70457(11) 0.0169(6) Uani 1 1 d . .
C24 C -0.0866(2) 0.4726(5) 0.71838(10) 0.0168(6) Uani 1 1 d . .
F24 F -0.11193(13) 0.2730(3) 0.69382(7) 0.0271(4) Uani 1 1 d . .
C25 C -0.1333(2) 0.5402(6) 0.75686(11) 0.0197(7) Uani 1 1 d . .
F25 F -0.20044(13) 0.4088(3) 0.76993(7) 0.0318(5) Uani 1 1 d . .
C26 C -0.1107(2) 0.7437(6) 0.78232(11) 0.0195(7) Uani 1 1 d . .
F26 F -0.15642(12) 0.8138(3) 0.81915(6) 0.0287(5) Uani 1 1 d . .
C27 C -0.0405(2) 0.8772(5) 0.76980(11) 0.0196(7) Uani 1 1 d . .
F27 F -0.01830(13) 1.0754(3) 0.79501(7) 0.0279(4) Uani 1 1 d . .
C28 C 0.0050(2) 0.8051(5) 0.73126(11) 0.0178(6) Uani 1 1 d . .
F28 F 0.07237(13) 0.9392(3) 0.71951(7) 0.0277(4) Uani 1 1 d . .
C31 C 0.1250(2) 0.6506(5) 0.48121(10) 0.0145(6) Uani 1 1 d . .
C32 C 0.1761(2) 0.5178(5) 0.46778(10) 0.0144(6) Uani 1 1 d . .
C33 C 0.24021(19) 0.3549(5) 0.45364(11) 0.0151(6) Uani 1 1 d . .
C34 C 0.2780(2) 0.3892(5) 0.40867(11) 0.0183(7) Uani 1 1 d . .
H34 H 0.257879 0.515292 0.386277 0.022 Uiso 1 1 calc R U
C35 C 0.3439(2) 0.2411(5) 0.39692(11) 0.0180(7) Uani 1 1 d . .
H35 H 0.369195 0.265622 0.366480 0.022 Uiso 1 1 calc R U
C36 C 0.37382(19) 0.0553(5) 0.42934(11) 0.0148(6) Uani 1 1 d . .
C37 C 0.3340(2) 0.0148(5) 0.47291(11) 0.0172(6) Uani 1 1 d . .
H37 H 0.352279 -0.115393 0.494296 0.021 Uiso 1 1 calc R U
C38 C 0.2684(2) 0.1632(5) 0.48496(11) 0.0171(6) Uani 1 1 d . .
H38 H 0.241887 0.135273 0.514848 0.020 Uiso 1 1 calc R U
C39 C 0.4498(2) -0.0891(5) 0.41632(11) 0.0170(6) Uani 1 1 d . .
O39 O 0.49154(14) -0.0452(4) 0.38175(8) 0.0230(5) Uani 1 1 d . .
C40 C 0.5391(2) -0.4256(6) 0.43485(12) 0.0245(7) Uani 1 1 d . .
H40A H 0.516974 -0.494950 0.400295 0.037 Uiso 1 1 calc R U
H40B H 0.552081 -0.545782 0.461525 0.037 Uiso 1 1 calc R U
H40C H 0.596358 -0.338694 0.434634 0.037 Uiso 1 1 calc R U
O40 O 0.46758(14) -0.2738(4) 0.44682(8) 0.0206(5) Uani 1 1 d . .
C41 C 0.6709(2) 0.0453(5) 0.33932(12) 0.0221(7) Uani 1 1 d . .
H41 H 0.601066 0.045372 0.334222 0.027 Uiso 1 1 calc R U
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C2 C1 C3 122.3(3) . 3_576
C2 C1 H1 118.8 . .
C3 C1 H1 118.8 3_576 .
C1 C2 C3 119.1(3) . .
C1 C2 C21 120.3(2) . .
C3 C2 C21 120.6(2) . .
C1 C3 C2 118.6(3) 3_576 .
C1 C3 C31 117.7(2) 3_576 .
C2 C3 C31 123.8(3) . .
O21 C21 O22 123.2(3) . .
O21 C21 C2 126.0(2) . .
O22 C21 C2 110.8(2) . .
O22 C22 C23 105.8(2) . .
O22 C22 H22A 110.6 . .
C23 C22 H22A 110.6 . .
O22 C22 H22B 110.6 . .
C23 C22 H22B 110.6 . .
H22A C22 H22B 108.7 . .
C21 O22 C22 113.8(2) . .
C24 C23 C28 116.3(3) . .
C24 C23 C22 123.0(3) . .
C28 C23 C22 120.7(3) . .
F24 C24 C25 117.8(3) . .
F24 C24 C23 119.8(3) . .
C25 C24 C23 122.4(3) . .
F25 C25 C26 119.5(3) . .
F25 C25 C24 120.8(3) . .
C26 C25 C24 119.7(3) . .
F26 C26 C25 120.4(3) . .
F26 C26 C27 119.8(3) . .
C25 C26 C27 119.8(3) . .
F27 C27 C28 121.2(3) . .
F27 C27 C26 119.6(3) . .
C28 C27 C26 119.3(3) . .
F28 C28 C27 118.0(3) . .
F28 C28 C23 119.4(3) . .
C27 C28 C23 122.6(3) . .
C32 C31 C3 174.0(3) . .
C31 C32 C33 177.6(3) . .
C38 C33 C34 118.8(3) . .
C38 C33 C32 121.0(2) . .
C34 C33 C32 120.2(3) . .
C35 C34 C33 120.3(3) . .
C35 C34 H34 119.9 . .
C33 C34 H34 119.9 . .
C34 C35 C36 120.4(3) . .
C34 C35 H35 119.8 . .
C36 C35 H35 119.8 . .
C35 C36 C37 119.6(3) . .
C35 C36 C39 117.6(2) . .
C37 C36 C39 122.7(3) . .
C38 C37 C36 120.1(3) . .
C38 C37 H37 120.0 . .
C36 C37 H37 120.0 . .
C37 C38 C33 120.7(3) . .
C37 C38 H38 119.6 . .
C33 C38 H38 119.6 . .
O39 C39 O40 123.1(3) . .
O39 C39 C36 123.9(3) . .
O40 C39 C36 113.0(2) . .
O40 C40 H40A 109.5 . .
O40 C40 H40B 109.5 . .
H40A C40 H40B 109.5 . .
O40 C40 H40C 109.5 . .
H40A C40 H40C 109.5 . .
H40B C40 H40C 109.5 . .
C39 O40 C40 115.5(2) . .
Cl3 C41 Cl1 111.45(17) . .
Cl3 C41 Cl2 110.48(17) . .
Cl1 C41 Cl2 110.51(17) . .
Cl3 C41 H41 108.1 . .
Cl1 C41 H41 108.1 . .
Cl2 C41 H41 108.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C41 1.756(3) .
C1 C2 1.384(4) .
C1 C3 1.398(4) 3_576
C1 H1 0.9500 .
C2 C3 1.408(4) .
C2 C21 1.491(4) .
Cl2 C41 1.758(3) .
Cl3 C41 1.748(3) .
C3 C31 1.442(4) .
C21 O21 1.195(3) .
C21 O22 1.353(3) .
C22 O22 1.448(3) .
C22 C23 1.498(4) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 C24 1.379(4) .
C23 C28 1.385(4) .
C24 F24 1.348(3) .
C24 C25 1.378(4) .
C25 F25 1.342(3) .
C25 C26 1.372(4) .
C26 F26 1.338(3) .
C26 C27 1.378(4) .
C27 F27 1.341(3) .
C27 C28 1.376(4) .
C28 F28 1.341(3) .
C31 C32 1.178(4) .
C32 C33 1.436(4) .
C33 C38 1.400(4) .
C33 C34 1.405(4) .
C34 C35 1.375(4) .
C34 H34 0.9500 .
C35 C36 1.392(4) .
C35 H35 0.9500 .
C36 C37 1.394(4) .
C36 C39 1.486(4) .
C37 C38 1.376(4) .
C37 H37 0.9500 .
C38 H38 0.9500 .
C39 O39 1.212(3) .
C39 O40 1.336(4) .
C40 O40 1.452(3) .
C40 H40A 0.9800 .
C40 H40B 0.9800 .
C40 H40C 0.9800 .
C41 H41 1.0000 .
