Tandem semipinacol-type 1,2-carbon migration/aldol reaction toward the construction of [5-6-7] all-carbon tricyclic core of Calyciphylline A-type alkaloids.
Yang, Ming; Wang, Lin; He, Zheng-He; Wang, Shao-Hua; Zhang, Shu-Yu; Tu, Yong-Qiang; Zhang, Fu-Min; Organic letters 14 (2012) 5114–5117; doi:10.1021/ol302386g

data_1508683
_publ_section_title
;
 Tandem semipinacol-type 1,2-carbon migration/aldol reaction toward the
 construction of [5-6-7] all-carbon tricyclic core of Calyciphylline
 A-type alkaloids.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5114
_journal_page_last               5117
_journal_paper_doi               10.1021/ol302386g
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C20 H22 O3'
_chemical_formula_sum            'C20 H22 O3'
_chemical_formula_weight         310.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-08-23
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  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.30(4)
_cell_length_b                   18.67(8)
_cell_length_c                   19.80(4)
_cell_measurement_reflns_used    3008
_cell_measurement_temperature    239.05(10)
_cell_measurement_theta_max      28.7519
_cell_measurement_theta_min      2.9938
_cell_volume                     3438(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      239.05(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9854
_diffrn_measured_fraction_theta_max 0.9405
_diffrn_measurement_details
;
  1 omega   35.00   61.40   1.2000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.9710  178.0000   90.0000 22

  2 omega  -12.00   15.60   1.2000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.9710 -101.0000  -12.0000 23

  3 omega    1.00   67.00   1.2000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3304 -101.0000  167.0000 55

  4 omega   10.00   49.60   1.2000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3304   57.0000    0.0000 33

  5 omega   42.00   81.60   1.2000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3304  178.0000    0.0000 33
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0206999000
_diffrn_orient_matrix_UB_12      0.0292529000
_diffrn_orient_matrix_UB_13      -0.0218251000
_diffrn_orient_matrix_UB_21      0.0518711000
_diffrn_orient_matrix_UB_22      0.0233631000
_diffrn_orient_matrix_UB_23      0.0139906000
_diffrn_orient_matrix_UB_31      0.0483517000
_diffrn_orient_matrix_UB_32      -0.0125181000
_diffrn_orient_matrix_UB_33      -0.0244134000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10387
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.00
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3422
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0562
_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^)+(0.0538P)^2^+1.0998P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1530
_reflns_number_gt                2320
_reflns_number_total             3422
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302386g_si_002.cif
_cod_data_source_block           yangm120813
_cod_original_cell_volume        3437(20)
_cod_database_code               1508683
_reflns_odcompleteness_completeness 98.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63