Photo-accelerated “Click” Reaction between Diarylsydnone and Ring-strained Alkyne for Bioorthogonal Ligation
Zhang, Xiaocui; Wu, Xueting; Jiang, Shichao; Gao, Jingshuo; Yao, Zhuojun; Deng, Jiajie; Zhang, Linmeng; Yu, Zhipeng; Chemical Communications  (2019) –; doi:10.1039/C9CC02882J

data_7123552
_publ_section_title
;
 Photo-accelerated &#x201C;Click&#x201D; Reaction between Diarylsydnone
 and Ring-strained Alkyne for Bioorthogonal Ligation
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC02882J
_journal_year                    2019
_chemical_formula_moiety         'C24 H22 F4 N2 O'
_chemical_formula_sum            'C24 H22 F4 N2 O'
_chemical_formula_weight         430.43
_chemical_name_common            5bd-dark
_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     direct
_audit_creation_date             2018-09-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-20 deposited with the CCDC.    2019-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                93.263(4)
_cell_angle_beta                 95.198(5)
_cell_angle_gamma                106.430(5)
_cell_formula_units_Z            2
_cell_length_a                   5.7422(4)
_cell_length_b                   8.6225(4)
_cell_length_c                   22.5087(13)
_cell_measurement_reflns_used    2202
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.1060
_cell_measurement_theta_min      3.5160
_cell_volume                     1060.57(11)
_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    'ShelXS (Sheldrick, 2008)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -42.00   52.40   0.8000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   77.0000 -120.0000 118

  2 omega  -25.00   23.00   0.8000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  -60.0000 60

  3 omega  -25.00   15.00   0.8000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  120.0000 50

  4 omega  -80.00    2.40   0.8000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -38.0000  -60.0000 103

  5 omega  -81.00  -26.60   0.8000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -77.0000  120.0000 68

  6 omega  -15.00   11.40   0.8000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -77.0000  120.0000 33

  7 omega   38.00   88.40   0.8000   19.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  178.0000  150.0000 63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0780476000
_diffrn_orient_matrix_UB_12      -0.0505152000
_diffrn_orient_matrix_UB_13      0.0028640000
_diffrn_orient_matrix_UB_21      0.0332668000
_diffrn_orient_matrix_UB_22      0.0290042000
_diffrn_orient_matrix_UB_23      0.0306050000
_diffrn_orient_matrix_UB_31      -0.0979568000
_diffrn_orient_matrix_UB_32      -0.0633859000
_diffrn_orient_matrix_UB_33      0.0079942000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9014
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.197
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96998
_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            ??
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.0656
_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^)+(0.0859P)^2^+0.2469P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1707
_refine_ls_wR_factor_ref         0.1993
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2418
_reflns_number_total             4338
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc02882j2.cif
_cod_data_source_block           180921_s1_zxc
_cod_original_cell_volume        1060.56(11)
_cod_database_code               7123552
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2f3
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.964
_reflns_odcompleteness_completeness 99.84
_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
 At 1.5 times of:
  All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O1) = Uanis(O1A)
Uanis(C7) = Uanis(C7A)
Uanis(C5) = Uanis(C5A)
Uanis(C6) = Uanis(C6A)
3. Others
 Sof(H24C)=Sof(H24D)=Sof(O1A)=Sof(H1A)=1-FVAR(1)
 Sof(H24A)=Sof(H24B)=Sof(O1)=Sof(H1)=FVAR(1)
 Sof(H4BC)=Sof(H4BD)=Sof(H8BC)=Sof(H8BD)=Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6A)=
 Sof(C7A)=Sof(H7A)=1-FVAR(2)
 Sof(H4AA)=Sof(H4AB)=Sof(H8AA)=Sof(H8AB)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=
 Sof(C7)=Sof(H7)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C5A(H5A), C6A(H6A), C7A(H7A)
4.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4AA,H4AB), C4(H4BC,H4BD), C8(H8AA,H8AB), C8(H8BC,H8BD),
 C9(H9A,H9B), C24(H24A,H24B), C24(H24C,H24D)
4.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C15(H15), C16(H16), C19(H19), C20(H20), C22(H22), C23(H23)
4.d Tetrahedral OH refined with riding coordinates:
 O1A(H1A)
4.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              90280
_olex2_submission_special_instructions 'No special instructions were received'