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_4125238
_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(C20 H12 F6 N4), C H Cl3'
_chemical_formula_sum            'C41 H25 Cl3 F12 N8'
_chemical_formula_weight         964.04
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-06-15
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.425(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.468(2)
_cell_length_b                   7.5319(7)
_cell_length_c                   27.491(3)
_cell_measurement_reflns_used    5075
_cell_measurement_temperature    143.00(10)
_cell_measurement_theta_max      23.9550
_cell_measurement_theta_min      3.2690
_cell_volume                     4154.1(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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      143.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -32.00   52.00   0.2000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   57.0000    0.0000 420

  2 omega   13.00   39.00   0.2000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   57.0000 -120.0000 130

  3 omega  -15.00   12.00   0.2000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   57.0000 -120.0000 135

  4 omega  -35.00  -10.00   0.2000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  128.0000 -104.0000 125

  5 omega  -42.00   53.00   0.2000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   77.0000 -120.0000 475

  6 omega  -67.00  -42.00   0.2000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  142.0000   67.0000 125

  7 omega  -24.00   24.00   0.2000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000 -120.0000 240

  8 omega   30.00   70.00   0.2000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       16.6856 -128.0000 -178.0000 200

  9 omega   20.00   45.00   0.2000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       16.6856 -142.0000   10.0000 125

 10 omega  -87.00  -62.00   0.2000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669 -178.0000  -90.0000 125
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0264691000
_diffrn_orient_matrix_UB_12      0.0128820000
_diffrn_orient_matrix_UB_13      -0.0206402000
_diffrn_orient_matrix_UB_21      0.0227488000
_diffrn_orient_matrix_UB_22      -0.0082480000
_diffrn_orient_matrix_UB_23      -0.0162667000
_diffrn_orient_matrix_UB_31      -0.0056685000
_diffrn_orient_matrix_UB_32      -0.0929289000
_diffrn_orient_matrix_UB_33      -0.0014286000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            34488
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         2.889
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91608
_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    1.541
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1944
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0020(6)
_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   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     630
_refine_ls_number_reflns         8487
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1193
_refine_ls_R_factor_gt           0.0727
_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^)+(0.1056P)^2^+1.0806P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2070
_refine_ls_wR_factor_ref         0.2446
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4713
_reflns_number_total             8487
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b03890_si_011.cif
_cod_data_source_block           160614_s4_cyy
_cod_depositor_comments
'Adding full bibliography for 4125235--4125245.cif.'
_cod_original_cell_volume        4154.0(8)
_cod_database_code               4125238
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         c12h12n2f1
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.911
_reflns_odcompleteness_completeness 99.48
_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, All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F3) = Uanis(F3A)
Uanis(F2) = Uanis(F2A)
Uanis(F1) = Uanis(F1A)
Uanis(F5) = Uanis(F5A)
Uanis(F6) = Uanis(F6A)
Uanis(F4) = Uanis(F4A)
Uanis(F11) = Uanis(F11A)
Uanis(F10) = Uanis(F10A)
Uanis(F12) = Uanis(F12A)
Uanis(F8) = Uanis(F8A)
Uanis(F9) = Uanis(F9A)
Uanis(F7) = Uanis(F7A)
Uanis(Cl3A) = Uanis(Cl3B)
Uanis(Cl1A) = Uanis(Cl1B)
Uanis(Cl2A) = Uanis(Cl2B)
3. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
 Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(2)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(2)
 Sof(F10A)=Sof(F11A)=Sof(F12A)=1-FVAR(3)
 Sof(F10)=Sof(F11)=Sof(F12)=FVAR(3)
 Sof(F7A)=Sof(F8A)=Sof(F9A)=1-FVAR(4)
 Sof(F7)=Sof(F8)=Sof(F9)=FVAR(4)
 Sof(H41A)=Sof(Cl1B)=Sof(Cl2B)=Sof(Cl3B)=1-FVAR(5)
 Sof(H41)=Sof(Cl1A)=Sof(Cl2A)=Sof(Cl3A)=FVAR(5)
4.a Ternary CH refined with riding coordinates:
 C41(H41A), C41(H41)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C12(H12), C13(H13), C15(H15), C16(H16), C18(H18),
 C19(H19), C22(H22), C24(H24), C26(H26), C32(H32), C33(H33), C35(H35), C36(H36),
  C38(H38), C39(H39)
4.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C40(H40A,H40B,H40C)
;
_shelx_res_checksum              38184
_shelx_hkl_checksum              17486
_olex2_submission_special_instructions 'No special instructions were received'