One-pot synthesis of multisubstituted butyrolactonimidates: total synthesis of (-)-nephrosteranic Acid.
Wang, Huijing; Tang, Pei; Zhou, Qilong; Zhang, Dan; Chen, Zhitao; Huang, Hongxiu; Qin, Yong; The Journal of organic chemistry 80 (2015) 2494–2502; doi:10.1021/jo5029166

data_4030688
_publ_section_title
;
 One-pot synthesis of multisubstituted butyrolactonimidates: total
 synthesis of (-)-nephrosteranic Acid.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2494
_journal_page_last               2502
_journal_paper_doi               10.1021/jo5029166
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C21 H31 N O6 S'
_chemical_formula_sum            'C21 H31 N O6 S'
_chemical_formula_weight         425.53
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-04-10
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7841(5)
_cell_length_b                   9.9078(5)
_cell_length_c                   27.3053(14)
_cell_measurement_reflns_used    3221
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.5200
_cell_measurement_theta_min      3.1670
_cell_volume                     2376.4(2)
_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, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -26.00   -1.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3611  -97.0000   89.0000 25

  2 omega  -27.00    1.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1580  -97.0000   89.0000 28

  3 omega   -8.00   18.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1580   97.0000 -162.0000 26

  4 omega   -7.00   25.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3611  -99.0000  -60.0000 32

  5 omega  -39.00   51.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3611   57.0000  -60.0000 90

  6 omega    9.00   56.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1580  -97.0000   89.0000 47
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0380154000
_diffrn_orient_matrix_UB_12      0.0310039000
_diffrn_orient_matrix_UB_13      -0.0199674000
_diffrn_orient_matrix_UB_21      -0.0062007000
_diffrn_orient_matrix_UB_22      0.0606719000
_diffrn_orient_matrix_UB_23      0.0136303000
_diffrn_orient_matrix_UB_31      0.0710132000
_diffrn_orient_matrix_UB_32      0.0218885000
_diffrn_orient_matrix_UB_33      -0.0094937000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0761
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            11332
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.984
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93090
_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
;
;
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_description
;
;
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 865 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.06(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         4716
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0608
_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^)+(0.0533P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1430
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_full    0.950
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                2869
_reflns_number_total             4716
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5029166_si_001.cif
_cod_data_source_block           140409_s1_lyf_m
_cod_depositor_comments          'Adding full bibliography for 4030688.cif.'
_cod_database_code               4030688
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         c12h14n2o3s1
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.951
_reflns_odcompleteness_completeness 99.57
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C17(H17A,H17B,
 H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              22509
_shelx_hkl_checksum              52047