Enantioselective Total Syntheses of Various Amphilectane and Serrulatane Diterpenoids via Cope Rearrangements.
Yu, Xuerong; Su, Fan; Liu, Chang; Yuan, Haosen; Zhao, Shan; Zhou, Zhiyao; Quan, Tianfei; Luo, Tuoping; Journal of the American Chemical Society 138 (2016) 6261–6270; doi:10.1021/jacs.6b02624

data_4130351
_publ_section_title
;
 Enantioselective Total Syntheses of Various Amphilectane and Serrulatane
 Diterpenoids via Cope Rearrangements.
;
_journal_issue                   19
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6261
_journal_page_last               6270
_journal_paper_doi               10.1021/jacs.6b02624
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C22 H25 N O4'
_chemical_formula_sum            'C22 H25 N O4'
_chemical_formula_weight         367.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-09-16
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                69.445(10)
_cell_angle_beta                 88.471(8)
_cell_angle_gamma                82.126(9)
_cell_formula_units_Z            2
_cell_length_a                   6.8007(6)
_cell_length_b                   10.8026(13)
_cell_length_c                   14.4909(13)
_cell_measurement_reflns_used    1333
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      71.8010
_cell_measurement_theta_min      4.4300
_cell_volume                     987.14(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9954
_diffrn_measured_fraction_theta_max 0.9604
_diffrn_measurement_details
;
  1 omega  -50.00   35.00   1.0000    2.9100
omega____ theta____ kappa____ phi______ frames
    -      -40.6056   38.0000   30.0000 85

  2 omega  -40.00   30.00   1.0000    2.9100
omega____ theta____ kappa____ phi______ frames
    -      -40.6056   38.0000  150.0000 70

  3 omega -113.00  -11.00   1.0000    2.9100
omega____ theta____ kappa____ phi______ frames
    -      -40.6056  -57.0000 -120.0000 102

  4 omega   61.00  117.00   1.0000    2.9100
omega____ theta____ kappa____ phi______ frames
    -       40.6056  178.0000  -60.0000 56

  5 omega   61.00  129.00   1.0000    2.9100
omega____ theta____ kappa____ phi______ frames
    -       40.6056  178.0000 -180.0000 68

  6 omega   41.00  121.00   1.0000   11.6500
omega____ theta____ kappa____ phi______ frames
    -      107.3775 -125.0000 -150.0000 80

  7 omega   77.00  178.00   1.0000   11.6500
omega____ theta____ kappa____ phi______ frames
    -      107.3775   30.0000   60.0000 101

  8 omega   33.00   91.00   1.0000   11.6500
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -30.0000  -90.0000 58

  9 omega   88.00  114.00   1.0000   11.6500
omega____ theta____ kappa____ phi______ frames
    -      107.3775   30.0000  -30.0000 26

 10 omega   23.00   99.00   1.0000   11.6500
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -94.0000  -60.0000 76

 11 omega  124.00  166.00   1.0000   11.6500
omega____ theta____ kappa____ phi______ frames
    -      107.3775   30.0000  -30.0000 42

 12 omega  114.00  141.00   1.0000   11.6500
omega____ theta____ kappa____ phi______ frames
    -      107.3775  125.0000 -150.0000 27

 13 omega  149.00  176.00   1.0000   11.6500
omega____ theta____ kappa____ phi______ frames
    -      107.3775  125.0000 -150.0000 27

 14 omega   50.00  107.00   1.0000   11.6500
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -94.0000    0.0000 57

 15 omega   33.00   83.00   1.0000   11.6500
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -30.0000   60.0000 50

 16 omega   95.00  153.00   1.0000   11.6500
omega____ theta____ kappa____ phi______ frames
    -      107.3775  125.0000  -30.0000 58

 17 omega  106.00  177.00   1.0000   11.6500
omega____ theta____ kappa____ phi______ frames
    -      107.3775  125.0000    0.0000 71

 18 omega   50.00  126.00   1.0000   11.6500
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -61.0000    0.0000 76
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.2109448000
_diffrn_orient_matrix_UB_12      0.0286872000
_diffrn_orient_matrix_UB_13      -0.0339695000
_diffrn_orient_matrix_UB_21      -0.0594027000
_diffrn_orient_matrix_UB_22      0.0169308000
_diffrn_orient_matrix_UB_23      -0.1060388000
_diffrn_orient_matrix_UB_31      -0.0655646000
_diffrn_orient_matrix_UB_32      0.1500906000
_diffrn_orient_matrix_UB_33      -0.0223661000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0781
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6411
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.129
_diffrn_reflns_theta_min         3.258
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_description
;
;
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3807
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1163
_refine_ls_R_factor_gt           0.0738
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1011P)^2^+0.1144P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1958
_refine_ls_wR_factor_ref         0.2342
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2189
_reflns_number_total             3807
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b02624_si_002.cif
_cod_data_source_block           exp_3927
_cod_original_cell_volume        987.14(18)
_cod_database_code               4130351
_chemical_oxdiff_formula         'C20 H20 N1 O4'
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C12(H12A,H12B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C16(H16), C21(H21)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C)
;
_shelx_estimated_absorpt_t_max   0.935
_shelx_estimated_absorpt_t_min   0.875
_shelxl_version_number           2013-3