Facile access to diverse all-carbon quaternary center containing spirobicycles by exploring a tandem Castro–Stephens coupling/acyloxy shift/cyclization/semipinacol rearrangement sequence
Zhang, Ye; Zheng, Tian-Lu; Cheng, Fu; Dai, Kun-Long; Zhang, Kun; Ma, Ai-Jun; Zhang, Fu-Min; Zhang, Xiao-Ming; Wang, Shao-Hua; Tu, Yong-Qiang; Chemical Science 11 (2020) 3878–3884; doi:10.1039/D0SC00102C

data_1557618
_publ_section_title
;
 Facile access to diverse all-carbon quaternary center containing
 spirobicycles by exploring a tandem Castro--Stephens coupling/acyloxy
 shift/cyclization/semipinacol rearrangement sequence
;
_journal_issue                   15
_journal_name_full               'Chemical Science'
_journal_page_first              3878
_journal_page_last               3884
_journal_paper_doi               10.1039/D0SC00102C
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C22 H30 N2 O4 S'
_chemical_formula_sum            'C22 H30 N2 O4 S'
_chemical_formula_weight         418.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-05-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2019-10-29 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.667(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9610(3)
_cell_length_b                   17.5295(6)
_cell_length_c                   13.2899(4)
_cell_measurement_reflns_used    2956
_cell_measurement_temperature    295.3(2)
_cell_measurement_theta_max      69.6190
_cell_measurement_theta_min      5.0230
_cell_volume                     2272.62(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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      295.3(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
  1 omega  -29.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   57.0000 -150.0000 64

  2 omega  -79.00  -44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000 -120.0000 35

  3 omega  -76.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  -30.0000 42

  4 omega   32.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -60.0000 87

  5 omega   33.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 88

  6 omega  102.00  132.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   90.0000 30

  7 omega  146.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 29

  8 omega   39.00  139.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 100

  9 omega  116.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000  -60.0000 61

 10 omega   35.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 30

 11 omega   35.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 58

 12 omega   35.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 56

 13 omega   63.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 25

 14 omega   57.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -30.0000 37

 15 omega   64.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000 -120.0000 39

 16 omega  115.00  166.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000 -120.0000 51

 17 omega   44.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -180.0000 44
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1564485000
_diffrn_orient_matrix_UB_12      0.0066793000
_diffrn_orient_matrix_UB_13      0.0105267000
_diffrn_orient_matrix_UB_21      0.0102671000
_diffrn_orient_matrix_UB_22      0.0408583000
_diffrn_orient_matrix_UB_23      0.1039223000
_diffrn_orient_matrix_UB_31      0.0188890000
_diffrn_orient_matrix_UB_32      -0.0774888000
_diffrn_orient_matrix_UB_33      0.0557221000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7941
_diffrn_reflns_theta_full        66.59
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_min         4.23
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.501
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48170
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.856
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         3890
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0565
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0918P)^2^+1.0790P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1590
_refine_ls_wR_factor_ref         0.1700
_reflns_number_gt                3232
_reflns_number_total             3890
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0sc00102c2.cif
_cod_data_source_block           zhangy_0518
_cod_depositor_comments
;Adding full bibliography for 1557613--1557618.cif.

 Adding full bibliography for 1557613--1557618.cif.
;
_cod_database_code               1557618
_reflns_odcompleteness_completeness 96.72
_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 Ternary CH refined with riding coordinates:
 C3(H3), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C17(H17), C18(H18), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C22(H22A,H22B,
 H22C)
;
_olex2_date_sample_data_collection 2018-05-18
_olex2_submission_special_instructions 'No special instructions were received'