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_4125237
_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         'C23 H20.07 N6'
_chemical_formula_sum            'C23 H20.03 N6'
_chemical_formula_weight         380.48
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-06-30
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 115.826(13)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   33.375(3)
_cell_length_b                   8.0465(5)
_cell_length_c                   32.417(4)
_cell_measurement_reflns_used    2670
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.8860
_cell_measurement_theta_min      3.7240
_cell_volume                     7836.1(16)
_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_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details
;
  1 omega   -9.00   21.00   0.3000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  120.0000 100

  2 omega  -54.00   43.20   0.3000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669    0.0000 -120.0000 324

  3 omega  -83.00   10.00   0.3000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -77.0000 -120.0000 310
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0147415000
_diffrn_orient_matrix_UB_12      0.0142905000
_diffrn_orient_matrix_UB_13      -0.0233385000
_diffrn_orient_matrix_UB_21      0.0164057000
_diffrn_orient_matrix_UB_22      -0.0289755000
_diffrn_orient_matrix_UB_23      -0.0066085000
_diffrn_orient_matrix_UB_31      -0.0084034000
_diffrn_orient_matrix_UB_32      -0.0820775000
_diffrn_orient_matrix_UB_33      -0.0017474000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            16753
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.925
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90452
_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    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             3201
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     536
_refine_ls_number_reflns         7700
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1042
_refine_ls_R_factor_gt           0.0602
_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^)+(0.0709P)^2^+2.8439P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1454
_refine_ls_wR_factor_ref         0.1759
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4573
_reflns_number_total             7700
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b03890_si_013.cif
_cod_data_source_block           160629_s3_cyy
_cod_depositor_comments
'Adding full bibliography for 4125235--4125245.cif.'
_cod_original_cell_volume        7836.1(15)
_cod_database_code               4125237
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         c12h12n2o3
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.968
_reflns_odcompleteness_completeness 95.92
_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,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C42A) = Uanis(C42)
Uanis(C43) = Uanis(C43A)
Uanis(C45A) = Uanis(C45)
Uanis(C46) = Uanis(C46A)
3. Others
 Sof(C42)=Sof(H42A)=Sof(H42B)=Sof(C45)=Sof(H45A)=Sof(H45B)=Sof(C43A)=Sof(H43C)=
 Sof(H43D)=Sof(C46A)=Sof(H46C)=Sof(H46D)=1-FVAR(1)
 Sof(H44A)=Sof(H44B)=Sof(H44C)=Sof(H44D)=Sof(C43)=Sof(H43A)=Sof(H43B)=Sof(C46)=
 Sof(H46A)=Sof(H46B)=Sof(C42A)=Sof(H42C)=Sof(H42D)=Sof(C45A)=Sof(H45C)=
 Sof(H45D)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C44(H44A,H44B), C44(H44C,H44D), C42(H42A,H42B), C43(H43A,H43B), C45(H45A,
 H45B), C46(H46A,H46B), C42A(H42C,H42D), C43A(H43C,H43D), C45A(H45C,H45D),
 C46A(H46C,H46D), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,
 H22B), C23(H23A,H23B)
4.b Aromatic/amide H refined with riding coordinates:
 C25(H25), C26(H26), C28(H28), C29(H29), C33(H33), C34(H34), C37(H37),
 C38(H38), C40(H40), C41(H41), C2(H2), C3(H3), C5(H5), C6(H6), C10(H10),
 C11(H11), C14(H14), C15(H15), C17(H17), C18(H18)
;
_shelx_res_checksum              65479
_shelx_hkl_checksum              43210
_olex2_submission_special_instructions 'No special instructions were received'