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_4125240
_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         'C19 H16 Cl N5'
_chemical_formula_sum            'C19 H16 Cl N5'
_chemical_formula_weight         349.82
_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             2014-06-22
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.18 svn.r2945 for OlexSys, GUI svn.r4846)
;
_cell_angle_alpha                100.727(4)
_cell_angle_beta                 99.114(4)
_cell_angle_gamma                98.267(4)
_cell_formula_units_Z            2
_cell_length_a                   7.6508(4)
_cell_length_b                   8.3307(4)
_cell_length_c                   13.6240(6)
_cell_measurement_reflns_used    5320
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.4440
_cell_measurement_theta_min      5.4700
_cell_volume                     828.86(7)
_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 0.985
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -31.00   53.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000 -120.0000 84

  2 omega  -31.00   53.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000  120.0000 84

  3 omega  -33.00   55.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000   30.0000 88

  4 omega   20.00  104.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000    0.0000 84

  5 omega   20.00  104.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   30.0000 84

  6 omega    1.00   75.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000 -150.0000 74

  7 omega   10.00  104.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  150.0000 94

  8 omega   23.00   90.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000   90.0000 67

  9 omega   39.00  109.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 70

 10 omega   38.00   91.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

 11 omega   87.00  178.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  150.0000 91

 12 omega   38.00   91.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

 13 omega   41.00  126.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -30.0000 85

 14 omega  100.00  178.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 78

 15 omega   40.00   98.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 58

 16 omega   40.00   98.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

 17 omega   38.00   91.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 18 omega   40.00   98.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

 19 omega   38.00  116.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 78

 20 omega   87.00  178.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   30.0000 91

 21 omega   39.00  109.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 70

 22 omega   57.00  150.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -60.0000 93

 23 omega   39.00  109.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

 24 omega   37.00  146.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -180.0000 109

 25 omega   20.00  104.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   60.0000 84

 26 omega   10.00  104.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -60.0000 94

 27 omega   10.00  104.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000   90.0000 94

 28 omega  -33.00   55.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000  -60.0000 88

 29 omega   17.00  105.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000 -150.0000 88

 30 omega   10.00  104.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000 -120.0000 94

 31 omega   20.00  104.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  -90.0000 84

 32 omega   87.00  178.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 91

 33 omega   81.00  176.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 95

 34 omega   81.00  176.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 95

 35 omega   87.00  178.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   90.0000 91

 36 omega   87.00  178.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 91

 37 omega   91.00  176.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 85

 38 omega   81.00  176.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 95

 39 omega   91.00  176.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 85

 40 omega   91.00  176.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 85

 41 omega   81.00  176.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 95

 42 omega   81.00  176.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 95

 43 omega   81.00  176.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 95

 44 omega   91.00  176.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 85

 45 omega   70.00  178.00   1.0000    4.2400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -90.0000 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      -0.0599300000
_diffrn_orient_matrix_UB_12      -0.1332083000
_diffrn_orient_matrix_UB_13      -0.0994057000
_diffrn_orient_matrix_UB_21      0.0721052000
_diffrn_orient_matrix_UB_22      0.1261791000
_diffrn_orient_matrix_UB_23      -0.0599958000
_diffrn_orient_matrix_UB_31      0.1848477000
_diffrn_orient_matrix_UB_32      -0.0540992000
_diffrn_orient_matrix_UB_33      0.0162080000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14709
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         5.493
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.129
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19577
_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    1.402
_exptl_crystal_description       needle
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0549
_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^)+(0.1110P)^2^+0.0460P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1554
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2573
_reflns_number_total             2957
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b03890_si_007.cif
_cod_data_source_block           wj-6-2
_cod_depositor_comments
'Adding full bibliography for 4125235--4125245.cif.'
_cod_database_code               4125240
_shelxl_version_number           2014-1
_reflns_odcompleteness_completeness 99.97
_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:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              64859
_shelx_hkl_checksum              68924
_olex2_submission_special_instructions 'No special instructions were received'