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_4132233
_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         'C29 H18 N2 O8, C H4 O'
_chemical_formula_sum            'C30 H22 N2 O9'
_chemical_formula_weight         554.49
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-10-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.816(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0804(4)
_cell_length_b                   20.9776(8)
_cell_length_c                   12.4916(4)
_cell_measurement_reflns_used    3069
_cell_measurement_temperature    143.1(2)
_cell_measurement_theta_max      27.9810
_cell_measurement_theta_min      3.1030
_cell_volume                     2610.30(17)
_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_environment      N~2~
_diffrn_ambient_temperature      143.1(2)
_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  -28.00    8.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   57.0000  -90.0000 36

  2 omega  -26.00   49.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   57.0000   90.0000 75

  3 omega    5.00   76.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   77.0000  150.0000 71

  4 omega  -18.00   17.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000    0.0000 35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0377613000
_diffrn_orient_matrix_UB_12      -0.0263988000
_diffrn_orient_matrix_UB_13      -0.0141132000
_diffrn_orient_matrix_UB_21      0.0400359000
_diffrn_orient_matrix_UB_22      0.0207937000
_diffrn_orient_matrix_UB_23      -0.0264033000
_diffrn_orient_matrix_UB_31      0.0452266000
_diffrn_orient_matrix_UB_32      0.0035979000
_diffrn_orient_matrix_UB_33      0.0490524000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11815
_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         3.105
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81334
_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            colorless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         5334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0500P)^2^+0.5067P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1245
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3754
_reflns_number_total             5334
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b02493_si_004.cif
_cod_data_source_block           171018_s1_zlm
_cod_original_cell_volume        2610.30(16)
_cod_database_code               4132233
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.969
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C6(H6), C10(H10), C11(H11), C13(H13), C16(H16), C18(H18),
 C19(H19), C24(H24), C25(H25), C27(H27), C28(H28)
2.b Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C29(H29A,H29B,H29C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'