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_4125241
_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         'C21 H15 F6 N5'
_chemical_formula_sum            'C21 H15 F6 N5'
_chemical_formula_weight         451.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-01-02
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                77.253(4)
_cell_angle_beta                 76.240(5)
_cell_angle_gamma                83.065(4)
_cell_formula_units_Z            2
_cell_length_a                   7.4714(5)
_cell_length_b                   9.4834(4)
_cell_length_c                   15.0286(9)
_cell_measurement_reflns_used    2723
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.5790
_cell_measurement_theta_min      3.4100
_cell_volume                     1006.17(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL-2012 (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_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -25.00   24.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3611  -99.0000   90.0000 49

  2 omega  -23.00   25.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3611  -99.0000  -90.0000 48

  3 omega  -67.00  -41.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3611 -178.0000   30.0000 26

  4 omega  -23.00    3.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3611  -99.0000 -150.0000 26

  5 omega   36.00   94.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1580  178.0000  -60.0000 58

  6 omega   -6.00   83.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1580   38.0000   90.0000 89

  7 omega  -39.00   63.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1580  -19.0000 -120.0000 102

  8 omega  -39.00  -14.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3611   57.0000   60.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0085645000
_diffrn_orient_matrix_UB_12      0.0033057000
_diffrn_orient_matrix_UB_13      -0.0484311000
_diffrn_orient_matrix_UB_21      0.0912531000
_diffrn_orient_matrix_UB_22      0.0217382000
_diffrn_orient_matrix_UB_23      -0.0091341000
_diffrn_orient_matrix_UB_31      0.0346778000
_diffrn_orient_matrix_UB_32      -0.0736721000
_diffrn_orient_matrix_UB_33      0.0054321000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8302
_diffrn_reflns_point_group_measured_fraction_full 0.998
_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         2.863
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_description
;
;
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1016
_refine_ls_R_factor_gt           0.0678
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0870P)^2^+0.3826P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1693
_refine_ls_wR_factor_ref         0.1962
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2631
_reflns_number_total             4105
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b03890_si_006.cif
_cod_data_source_block           131230_s1_wj
_cod_depositor_comments
'Adding full bibliography for 4125235--4125245.cif.'
_cod_database_code               4125241
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         c12h12n2o3f6
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.962
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Uiso/Uaniso restraints and constraints
Uanis(F5A) = Uanis(F5B)
Uanis(F4A) = Uanis(F4B)
Uanis(F1A) = Uanis(F1B)
Uanis(F2A) = Uanis(F2B)
Uanis(F3A) = Uanis(F3B)
Uanis(F6A) = Uanis(F6B)
3. Others
 Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(F4B)=Sof(F5B)=1-FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=Sof(F5A)=FVAR(1)
 Sof(F6B)=1-FVAR(2)
 Sof(F6A)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C15(H15),
 C17(H17)
4.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              55401
_shelx_hkl_checksum              2250