Discovery of Fluorogenic Diarylsydnone-Alkene Photoligation: Conversion of ortho-Dual-Twisted Diarylsydnones into Planar Pyrazolines.
Zhang, Linmeng; Zhang, Xiaocui; Yao, Zhuojun; Jiang, Shichao; Deng, Jiajie; Li, Bo; Yu, Zhipeng; Journal of the American Chemical Society 140 (2018) 7390–7394; doi:10.1021/jacs.8b02493

data_4132231
_publ_section_title
;
 Discovery of Fluorogenic Diarylsydnone-Alkene Photoligation: Conversion
 of ortho-Dual-Twisted Diarylsydnones into Planar Pyrazolines.
;
_journal_issue                   24
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7390
_journal_page_last               7394
_journal_paper_doi               10.1021/jacs.8b02493
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C20 H19 F3 N2 O3'
_chemical_formula_sum            'C20 H19 F3 N2 O3'
_chemical_formula_weight         392.37
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-06-08
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.5187(16)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.47072(18)
_cell_length_b                   9.95859(17)
_cell_length_c                   33.1143(6)
_cell_measurement_reflns_used    4514
_cell_measurement_temperature    200
_cell_measurement_theta_max      72.4210
_cell_measurement_theta_min      5.3460
_cell_volume                     3758.26(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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      200
_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 0.977
_diffrn_measurement_details
;
  1 omega    1.00   75.00   1.0000    1.6800
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000   60.0000 74

  2 omega   23.00   90.00   1.0000    1.6800
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  -60.0000 67

  3 omega  -31.00   53.00   1.0000    1.6800
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000  -60.0000 84

  4 omega  -33.00   55.00   1.0000    1.6800
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000  150.0000 88

  5 omega    1.00   75.00   1.0000    1.6800
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  150.0000 74

  6 omega  -33.00   55.00   1.0000    1.6800
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000    0.0000 88

  7 omega  100.00  178.00   1.0000    6.7300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 78

  8 omega   40.00   98.00   1.0000    6.7300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

  9 omega   87.00  178.00   1.0000    6.7300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -60.0000 91

 10 omega   39.00  109.00   1.0000    6.7300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -151.0000 70

 11 omega  100.00  178.00   1.0000    6.7300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 78

 12 omega   87.00  178.00   1.0000    6.7300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   60.0000 91

 13 omega   41.00  126.00   1.0000    6.7300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -150.0000 85

 14 omega   38.00   91.00   1.0000    6.7300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 15 omega   20.00  104.00   1.0000    1.6800
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  -60.0000 84

 16 omega   10.00   89.00   1.0000    1.6800
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000 -180.0000 79

 17 omega   20.00  104.00   1.0000    1.6800
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   90.0000 84
;
_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      -0.0217392000
_diffrn_orient_matrix_UB_12      0.0163080000
_diffrn_orient_matrix_UB_13      -0.0465134000
_diffrn_orient_matrix_UB_21      -0.0470759000
_diffrn_orient_matrix_UB_22      0.1429904000
_diffrn_orient_matrix_UB_23      0.0054431000
_diffrn_orient_matrix_UB_31      0.1247979000
_diffrn_orient_matrix_UB_32      0.0567839000
_diffrn_orient_matrix_UB_33      -0.0003033000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            10669
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.628
_diffrn_reflns_theta_min         5.901
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.971
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67421
_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            'dull yellowish yellow'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.858
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3660
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0699
_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^)+(0.1050P)^2^+7.1057P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1920
_refine_ls_wR_factor_ref         0.1972
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3278
_reflns_number_total             3660
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b02493_si_005.cif
_cod_data_source_block           yzp-zlm-d-47-200k
_cod_original_cell_volume        3758.27(11)
_cod_database_code               4132231
_reflns_odcompleteness_completeness 99.89
_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:
 C00G(H00D,H00E)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00C(H00C), C00F(H00F), C00H(H00H), C00J(H00K),
 C00L(H00L), C00M(H00M)
2.c Idealised Me refined as rotating group:
 C00I(H00G,H00I,H00J), C00P(H00N,H00O,H00P), C00Q(H00Q,H00R,H00S)
;
_shelx_res_checksum              17258
_shelx_hkl_checksum              53343
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2017-06-07
_olex2_submission_special_instructions 'No special instructions were received'