Photoisomerization-enhanced 1,3-dipolar cycloaddition of carbon-bridged octocyclic azobenzene with photo-released nitrile imine for peptide stapling and imaging in live cells.
Deng, Jiajie; Wu, Xueting; Guo, Guiling; Zhao, Xiaohu; Yu, Zhipeng; Organic & biomolecular chemistry 18 (2020) 5602–5607; doi:10.1039/d0ob01027h

data_7157568
_publ_section_title
;
 Photoisomerization-enhanced 1,3-dipolar cycloaddition of carbon-bridged
 octocyclic azobenzene with photo-released nitrile imine for peptide
 stapling and imaging in live cells.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5602
_journal_page_last               5607
_journal_paper_doi               10.1039/d0ob01027h
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C31 H21 F3 N6 O'
_chemical_formula_sum            'C31 H21 F3 N6 O'
_chemical_formula_weight         550.54
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-04-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2020-03-23 deposited with the CCDC.	2020-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.5263(19)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.8293(3)
_cell_length_b                   16.2265(2)
_cell_length_c                   20.2270(3)
_cell_measurement_reflns_used    11672
_cell_measurement_temperature    141.3(2)
_cell_measurement_theta_max      72.3820
_cell_measurement_theta_min      4.0220
_cell_volume                     5205.93(15)
_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
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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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      141.3(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
  1 omega   23.00   90.00   1.0000    1.3800
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000   60.0000 67

  2 omega   20.00  104.00   1.0000    1.3800
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000 -120.0000 84

  3 omega   23.00   90.00   1.0000    1.3800
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  -60.0000 67

  4 omega  -31.00   53.00   1.0000    1.3800
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000 -120.0000 84

  5 omega  -31.00   63.00   1.0000    1.3800
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000  120.0000 94

  6 omega   20.00  104.00   1.0000    1.3800
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   90.0000 84

  7 omega    1.00   75.00   1.0000    1.3800
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000 -150.0000 74

  8 omega  100.00  178.00   1.0000    5.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 78

  9 omega   38.00   91.00   1.0000    5.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

 10 omega   39.00  109.00   1.0000    5.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 70

 11 omega   38.00   91.00   1.0000    5.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 12 omega   39.00  109.00   1.0000    5.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 70

 13 omega   39.00  109.00   1.0000    5.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 70

 14 omega   81.00  176.00   1.0000    5.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 95

 15 omega   40.00   87.00   1.0000    5.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 47

 16 omega   44.00   70.00   1.0000    5.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 26

 17 omega   65.00   91.00   1.0000    5.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 26

 18 omega  100.00  178.00   1.0000    5.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 78
;
_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      0.0330036000
_diffrn_orient_matrix_UB_12      0.0880145000
_diffrn_orient_matrix_UB_13      0.0214758000
_diffrn_orient_matrix_UB_21      -0.0910866000
_diffrn_orient_matrix_UB_22      0.0328519000
_diffrn_orient_matrix_UB_23      -0.0262727000
_diffrn_orient_matrix_UB_31      -0.0065140000
_diffrn_orient_matrix_UB_32      -0.0139491000
_diffrn_orient_matrix_UB_33      0.0733401000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28959
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.669
_diffrn_reflns_theta_min         4.639
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.866
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70834
_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_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       block
_exptl_crystal_F_000             2272
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.876
_refine_diff_density_min         -0.675
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     741
_refine_ls_number_reflns         10167
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0632
_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^)+(0.1163P)^2^+2.6658P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1728
_refine_ls_wR_factor_ref         0.1825
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8733
_reflns_number_total             10167
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01027h2.cif
_cod_data_source_block           yzp-c-31-142k
_cod_depositor_comments
'Adding full bibliography for 7157568--7157569.cif.'
_cod_original_cell_volume        5205.90(16)
_cod_database_code               7157568
_shelx_shelxl_version_number     2014/7
_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, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00Y(H00A,H00B), C01E(H01A,H01B), C022(H02D,H02E), C023(H02F,H02G)
2.b Aromatic/amide H refined with riding coordinates:
 C00R(H00R), C00V(H00V), C00X(H00X), C00Z(H00Z), C010(H010), C012(H012),
 C015(H015), C016(H016), C017(H017), C018(H018), C01A(H01C), C01D(H01D),
 C01F(H01F), C01I(H01I), C01J(H01J), C01O(H01O), C01P(H01P), C01R(H01R),
 C01S(H01S), C01T(H01T), C01U(H01U), C01W(H01W), C01X(H01X), C01Z(H01Z),
 C020(H020), C026(H026), C027(H027), C028(H028)
2.c Idealised Me refined as rotating group:
 C024(H02A,H02B,H02C), C02A(H02H,H02I,H02J)
;
_olex2_submission_special_instructions 'No special instructions were received'