Molecular Engineering of Mechanochromic Materials by Programmed C-H Arylation: Making a Counterpoint in the Chromism Trend.
Wu, Jie; Cheng, Yangyang; Lan, Jingbo; Wu, Di; Qian, Shengyou; Yan, Lipeng; He, Zhen; Li, Xiaoyu; Wang, Kai; Zou, Bo; You, Jingsong; Journal of the American Chemical Society 138 (2016) 12803–12812; doi:10.1021/jacs.6b03890

data_4125239
_publ_section_title
;
 Molecular Engineering of Mechanochromic Materials by Programmed C-H
 Arylation: Making a Counterpoint in the Chromism Trend.
;
_journal_issue                   39
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12803
_journal_page_last               12812
_journal_paper_doi               10.1021/jacs.6b03890
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C20 H12 F6 N4'
_chemical_formula_sum            'C20 H12 F6 N4'
_chemical_formula_weight         422.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2yc'
_space_group_name_H-M_alt        'I 1 2/c 1'
_symmetry_space_group_name_Hall  '-I 2yc'
_symmetry_space_group_name_H-M   'I 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-11-18
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.304(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.3500(3)
_cell_length_b                   10.0002(2)
_cell_length_c                   27.9606(7)
_cell_measurement_reflns_used    3899
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      72.4890
_cell_measurement_theta_min      4.6930
_cell_volume                     3693.68(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -31.00   53.00   1.0000    2.4900
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000  -90.0000 84

  2 omega   20.00  104.00   1.0000    2.4900
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000  -90.0000 84

  3 omega   20.00  104.00   1.0000    2.4900
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000 -180.0000 84

  4 omega   10.00  104.00   1.0000    2.4900
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000  150.0000 94

  5 omega    2.00   29.00   1.0000    2.4900
omega____ theta____ kappa____ phi______ frames
    -       36.5421   91.0000   82.1403 27

  6 omega    1.00   75.00   1.0000    2.4900
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000   30.0000 74

  7 omega   10.00  104.00   1.0000    2.4900
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000  120.0000 94

  8 omega   39.00  109.00   1.0000    9.9600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 70

  9 omega   38.00   91.00   1.0000    9.9600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

 10 omega   39.00  109.00   1.0000    9.9600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 70

 11 omega   91.00  176.00   1.0000    9.9600
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 85

 12 omega   38.00  116.00   1.0000    9.9600
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 78

 13 omega   57.00  150.00   1.0000    9.9600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 93

 14 omega   81.00  176.00   1.0000    9.9600
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 95

 15 omega   40.00   98.00   1.0000    9.9600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

 16 omega   90.00  175.00   1.0000    9.9600
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0282940000
_diffrn_orient_matrix_UB_12      -0.0770335000
_diffrn_orient_matrix_UB_13      -0.0477297000
_diffrn_orient_matrix_UB_21      0.0151216000
_diffrn_orient_matrix_UB_22      -0.1333848000
_diffrn_orient_matrix_UB_23      0.0276664000
_diffrn_orient_matrix_UB_31      -0.1121343000
_diffrn_orient_matrix_UB_32      0.0014654000
_diffrn_orient_matrix_UB_33      0.0074710000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            9890
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.992
_diffrn_reflns_theta_min         4.702
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.188
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       0.0020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3293
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0837
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1530P)^2^+3.6990P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2462
_refine_ls_wR_factor_ref         0.2585
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2756
_reflns_number_total             3293
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b03890_si_005.cif
_cod_data_source_block           wj001
_cod_depositor_comments
'Adding full bibliography for 4125235--4125245.cif.'
_cod_original_cell_volume        3693.70(15)
_cod_database_code               4125239
_shelxl_version_number           2014-1
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 F4, C20
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 F5, C20
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Others
 Sof(F6A)=1-FVAR(1)
 Sof(F6)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C14(H14), C16(H16), C7(H7), C2(H2), C11(H11), C10(H10), C3(H3),
 C8(H8)
4.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              65502
_shelx_hkl_checksum              54726
_olex2_submission_special_instructions 'No special instructions were received'