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_4125243
_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 H16 N6'
_chemical_formula_sum            'C20 H16 N6'
_chemical_formula_weight         340.39
_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     iterative
_audit_creation_date             2014-06-22
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.18 svn.r2945 for OlexSys, GUI svn.r4846)
;
_cell_angle_alpha                90
_cell_angle_beta                 115.192(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6566(6)
_cell_length_b                   30.6548(15)
_cell_length_c                   7.8558(6)
_cell_measurement_reflns_used    5236
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.4680
_cell_measurement_theta_min      5.7630
_cell_volume                     1668.5(2)
_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
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   23.00   90.00   1.0000    4.2600
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000 -150.0000 67

  2 omega   20.00  104.00   1.0000    4.2600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   60.0000 84

  3 omega  -31.00   53.00   1.0000    4.2600
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000   30.0000 84

  4 omega    1.00   75.00   1.0000    4.2600
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  -30.0000 74

  5 omega  -31.00   53.00   1.0000    4.2600
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000   90.0000 84

  6 omega   20.00  104.00   1.0000    4.2600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  -90.0000 84

  7 omega   38.00   91.00   1.0000   17.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

  8 omega   39.00  109.00   1.0000   17.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

  9 omega   38.00   91.00   1.0000   17.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

 10 omega   38.00   91.00   1.0000   17.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

 11 omega   87.00  178.00   1.0000   17.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -120.0000 91

 12 omega  100.00  178.00   1.0000   17.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 78

 13 omega   39.00  109.00   1.0000   17.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 70

 14 omega   57.00  150.00   1.0000   17.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  150.0000 93

 15 omega   40.00   98.00   1.0000   17.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 58

 16 omega   20.00  104.00   1.0000    4.2600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000    0.0000 84

 17 omega   10.00  104.00   1.0000    4.2600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000   90.0000 94

 18 omega   10.00  104.00   1.0000    4.2600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  150.0000 94

 19 omega  -33.00   55.00   1.0000    4.2600
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000  150.0000 88

 20 omega   10.00  104.00   1.0000    4.2600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000 -180.0000 94

 21 omega  -31.00   53.00   1.0000    4.2600
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000 -120.0000 84

 22 omega   87.00  178.00   1.0000   17.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   30.0000 91

 23 omega   87.00  178.00   1.0000   17.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -60.0000 91

 24 omega   91.00  176.00   1.0000   17.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 85

 25 omega   91.00  154.00   1.0000   17.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 63

 26 omega   70.00  178.00   1.0000   17.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  150.0000 108
;
_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      0.0825706000
_diffrn_orient_matrix_UB_12      0.0463196000
_diffrn_orient_matrix_UB_13      0.0119678000
_diffrn_orient_matrix_UB_21      -0.2063869000
_diffrn_orient_matrix_UB_22      0.0184446000
_diffrn_orient_matrix_UB_23      -0.0969538000
_diffrn_orient_matrix_UB_31      -0.0026825000
_diffrn_orient_matrix_UB_32      0.0063687000
_diffrn_orient_matrix_UB_33      0.1934100000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.988
_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       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            14907
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         5.773
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68256
_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    1.355
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2973
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0603
_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^)+(0.1180P)^2^+0.2540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1674
_refine_ls_wR_factor_ref         0.1783
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2525
_reflns_number_total             2973
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b03890_si_009.cif
_cod_data_source_block           wj-5
_cod_depositor_comments
'Adding full bibliography for 4125235--4125245.cif.'
_cod_database_code               4125243
_shelxl_version_number           2014-1
_reflns_odcompleteness_completeness 99.90
_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.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              93158
_shelx_hkl_checksum              15410
_olex2_submission_special_instructions 'No special instructions were received'