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_4125236
_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         '2(C19 H10 F6 N4), C H Cl3'
_chemical_formula_sum            'C39 H21 Cl3 F12 N8'
_chemical_formula_weight         935.99
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-06-16
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.240(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.0395(16)
_cell_length_b                   7.5585(7)
_cell_length_c                   35.865(4)
_cell_measurement_reflns_used    4765
_cell_measurement_temperature    143.05(10)
_cell_measurement_theta_max      25.7530
_cell_measurement_theta_min      3.0270
_cell_volume                     3998.8(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      143.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega    1.00   36.10   0.3000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2361   57.0000    0.0000 117

  2 omega    1.90   88.00   0.3000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2361   57.0000   90.0000 287

  3 omega   15.00   40.80   0.3000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2361 -132.0000   79.0000 86

  4 omega   44.00   83.00   0.3000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2361 -137.0000  -96.0000 130

  5 omega  -66.00  -39.00   0.3000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5174 -178.0000 -150.0000 90

  6 omega  -82.00    2.00   0.3000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5174  -38.0000  -30.0000 280

  7 omega  -62.00    6.10   0.3000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5174   19.0000   30.0000 227

  8 omega  -67.00  -42.70   0.3000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5174  137.0000  -34.0000 81

  9 omega  -39.00  -10.80   0.3000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5174   77.0000 -150.0000 94

 10 omega  -63.00  -38.70   0.3000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5174  132.0000  149.0000 81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0384196000
_diffrn_orient_matrix_UB_12      0.0098623000
_diffrn_orient_matrix_UB_13      0.0085796000
_diffrn_orient_matrix_UB_21      -0.0287535000
_diffrn_orient_matrix_UB_22      -0.0021506000
_diffrn_orient_matrix_UB_23      -0.0182086000
_diffrn_orient_matrix_UB_31      -0.0034268000
_diffrn_orient_matrix_UB_32      -0.0932135000
_diffrn_orient_matrix_UB_33      0.0013248000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0861
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            32164
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.919
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1880
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.0021(8)
_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   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     610
_refine_ls_number_reflns         8166
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.1331
_refine_ls_R_factor_gt           0.0853
_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/[\s^2^(Fo^2^)+(0.1437P)^2^+0.5825P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2497
_refine_ls_wR_factor_ref         0.2992
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4401
_reflns_number_total             8166
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b03890_si_012.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 4125235--4125245.cif.'
_cod_original_cell_volume        3998.7(7)
_cod_database_code               4125236
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         c12h12n2f3
_shelx_estimated_absorpt_t_max   0.937
_shelx_estimated_absorpt_t_min   0.880
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F12) = Uanis(F12A)
Uanis(F11) = Uanis(F11A)
Uanis(F10) = Uanis(F10A)
Uanis(F7) = Uanis(F7A)
Uanis(F8) = Uanis(F8A)
Uanis(F9) = Uanis(F9A)
Uanis(F4) = Uanis(F4A)
Uanis(F6) = Uanis(F6A)
Uanis(F5) = Uanis(F5A)
Uanis(F2) = Uanis(F2A)
Uanis(F1A) = Uanis(F1)
Uanis(F3) = Uanis(F3A)
Uanis(Cl2) = Uanis(Cl2A)
Uanis(Cl3) = Uanis(Cl3A)
Uanis(Cl1) = Uanis(Cl1A)
3. Others
 Sof(F10A)=Sof(F11A)=Sof(F12A)=1-FVAR(1)
 Sof(F10)=Sof(F11)=Sof(F12)=FVAR(1)
 Sof(F7A)=Sof(F8A)=Sof(F9A)=1-FVAR(2)
 Sof(F7)=Sof(F8)=Sof(F9)=FVAR(2)
 Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(3)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(3)
 Sof(F1)=Sof(F2A)=Sof(F3A)=1-FVAR(4)
 Sof(F2)=Sof(F3)=Sof(F1A)=FVAR(4)
 Sof(H39A)=Sof(Cl1A)=Sof(Cl2A)=Sof(Cl3A)=1-FVAR(5)
 Sof(H39)=Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=FVAR(5)
4.a Ternary CH refined with riding coordinates:
 C39(H39A), C39(H39)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C21(H21), C23(H23), C25(H25), C31(H31), C32(H32), C34(H34),
  C35(H35), C36(H36), C37(H37), C38(H38)
;
_shelx_res_checksum              62154
_shelx_hkl_checksum              79522
_olex2_submission_special_instructions 'No special instructions were received'