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_4125242
_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(C21 H15 F6 N5), C H2 Cl2'
_chemical_formula_sum            'C43 H32 Cl2 F12 N10'
_chemical_formula_weight         987.68
_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             2014-03-07
_audit_creation_method
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_cell_angle_alpha                76.578(3)
_cell_angle_beta                 86.891(3)
_cell_angle_gamma                87.608(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8375(3)
_cell_length_b                   14.8040(5)
_cell_length_c                   18.7620(6)
_cell_measurement_reflns_used    5628
_cell_measurement_temperature    143.00(10)
_cell_measurement_theta_max      27.7260
_cell_measurement_theta_min      3.3090
_cell_volume                     2113.36(13)
_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 (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      143.00(10)
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -63.00  -37.40   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3611 -178.0000  -30.0000 32

  2 omega  -25.00    9.40   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3611  -99.0000   30.0000 43

  3 omega  -16.00   18.40   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3611  -99.0000 -120.0000 43

  4 omega  -13.00   23.00   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3611  -99.0000  120.0000 45

  5 omega  -86.00  -58.80   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3611 -178.0000   30.0000 34

  6 omega  -37.00   39.00   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1580  -57.0000 -150.0000 95

  7 omega    0.00   88.00   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1580   38.0000  150.0000 110

  8 omega   41.00   93.00   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1580 -178.0000   30.0000 65

  9 omega  -51.00   36.20   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1580  -38.0000  -30.0000 109
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0594622000
_diffrn_orient_matrix_UB_12      0.0358935000
_diffrn_orient_matrix_UB_13      0.0045795000
_diffrn_orient_matrix_UB_21      -0.0442463000
_diffrn_orient_matrix_UB_22      -0.0318001000
_diffrn_orient_matrix_UB_23      0.0284117000
_diffrn_orient_matrix_UB_31      0.0522343000
_diffrn_orient_matrix_UB_32      0.0113561000
_diffrn_orient_matrix_UB_33      0.0261842000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.999
_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       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18833
_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         2.830
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96249
_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    1.552
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1004
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     612
_refine_ls_number_reflns         8640
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0625
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0563P)^2^+1.6476P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1609
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5743
_reflns_number_total             8640
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b03890_si_008.cif
_cod_data_source_block           140306_s3_wj
_cod_depositor_comments
'Adding full bibliography for 4125235--4125245.cif.'
_cod_original_cell_volume        2113.37(12)
_cod_database_code               4125242
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         c12h12n2o3
_shelx_estimated_absorpt_t_max   0.928
_shelx_estimated_absorpt_t_min   0.921
_reflns_odcompleteness_completeness 99.90
_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,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Cl2A) = Uanis(Cl2B)
3. Others
 Sof(H43D)=Sof(H43C)=Sof(Cl2B)=1-FVAR(1)
 Sof(H43A)=Sof(H43B)=Sof(Cl2A)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C43(H43A,H43B), C43(H43D,H43C)
4.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C25(H25), C28(H28), C29(H29), C31(H31), C32(H32), C34(H34),
 C36(H36), C38(H38), C3(H3), C4(H4), C7(H7), C8(H8), C10(H10), C11(H11),
 C13(H13), C15(H15), C17(H17)
4.c Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C40(H40A,H40B,H40C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C)
;
_shelx_res_checksum              96453
_shelx_hkl_checksum              36288
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'