Palladium-Catalyzed <i>syn</i>-Stereocontrolled Ring Opening of Oxabicyclic Alkenes with Arylsulfonyl Hydrazides.
Chen, Donghan; Yao, Yongqi; Yang, Wen; Lin, Qifu; Li, Huanyong; Wang, Lin; Chen, Shuqi; Tan, Yun; Yang, Dingqiao; The Journal of organic chemistry 84 (2019) 12481–12489; doi:10.1021/acs.joc.9b01957

data_4033969
_publ_section_title
;
 Palladium-Catalyzed <i>syn</i>-Stereocontrolled Ring Opening of
 Oxabicyclic Alkenes with Arylsulfonyl Hydrazides.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12481
_journal_page_last               12489
_journal_paper_doi               10.1021/acs.joc.9b01957
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C16 H13 N O3'
_chemical_formula_sum            'C16 H13 N O3'
_chemical_formula_weight         265.96
_space_group_crystal_system      tetragonal
_space_group_IT_number           85
_space_group_name_Hall           '-P 4a'
_space_group_name_H-M_alt        'P 4/n :2'
_symmetry_Int_Tables_number      85
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.3246(3)
_cell_length_b                   14.3246(3)
_cell_length_c                   13.4826(4)
_cell_measurement_reflns_used    1845
_cell_measurement_temperature    293
_cell_measurement_theta_max      62.2900
_cell_measurement_theta_min      4.5100
_cell_volume                     2766.55(12)
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0288
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.9844
_diffrn_measured_fraction_theta_max 0.9844
_diffrn_measurement_details
;
  1 omega   31.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934   57.0000 -120.0000 70

  2 omega   34.00   61.00   1.0000    3.3200
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000    0.0000 27

  3 omega   28.00   54.00   1.0000    3.3200
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000  -60.0000 26

  4 omega   24.00   65.00   1.0000    3.3200
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000  -30.0000 41

  5 omega   48.00   89.00   1.0000    3.3200
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000 -150.0000 41

  6 omega   19.00   70.00   1.0000    3.3200
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000 -150.0000 51

  7 omega   19.00   63.00   1.0000    3.3200
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000  150.0000 44

  8 omega   39.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934  178.0000  120.0000 26

  9 omega   78.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934  178.0000  -90.0000 27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0494264000
_diffrn_orient_matrix_UB_12      -0.0908893000
_diffrn_orient_matrix_UB_13      0.0315826000
_diffrn_orient_matrix_UB_21      -0.0946641000
_diffrn_orient_matrix_UB_22      -0.0509268000
_diffrn_orient_matrix_UB_23      0.0008395000
_diffrn_orient_matrix_UB_31      0.0136649000
_diffrn_orient_matrix_UB_32      -0.0264471000
_diffrn_orient_matrix_UB_33      -0.1097454000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4318
_diffrn_reflns_theta_full        62.8014
_diffrn_reflns_theta_max         62.80
_diffrn_reflns_theta_min         4.37
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79330
_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 yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.2833
_exptl_crystal_description       block
_exptl_crystal_F_000             1123.8133
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.2853
_refine_diff_density_min         -0.4169
_refine_diff_density_rms         0.1122
_refine_ls_d_res_high            0.8668
_refine_ls_d_res_low             10.1290
_refine_ls_goodness_of_fit_ref   1.0415
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2203
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0415
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0627
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1094P)^2^+0.1618P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1477
_refine_ls_wR_factor_ref         0.1584
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              0
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                1857
_reflns_number_total             2203
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo9b01957_si_001.cif
_cod_data_source_block           wanglin3-0417
_cod_depositor_comments
;

2020-10-09
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      'P 4/n'
_cod_original_formula_moiety     '0.67(C16 H13 N O3)'
_cod_original_formula_sum        'C10.667 H8.667 N0.667 O2'
_cod_original_formula_units_Z    12
_cod_original_formula_weight     178.19
_cod_database_code               4033969
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C002(H002), C005(H005)
2.b Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00J(H00J), C00I(H00I), C00C(H00C), C00E(H00E), C00H(H00H),
 C00D(H00D), C009(H009), C007(H007), C008(H008)
2.c Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_olex2_submission_special_instructions 'No special instructions were received'