Construction of the [6,5,7,5] Tetracyclic Core of Calyciphylline A Type Alkaloids via a Tandem Semipinacol Rearrangement/Nicholas Reaction.
Shao, Hui; Bao, Wen; Jing, Ze-Ran; Wang, Yun-Peng; Zhang, Fu-Min; Wang, Shao-Hua; Tu, Yong-Qiang; Organic letters 19 (2017) 4648–4651; doi:10.1021/acs.orglett.7b02274

data_1547034
_publ_section_title
;
 Construction of the [6,5,7,5] Tetracyclic Core of Calyciphylline A Type
 Alkaloids via a Tandem Semipinacol Rearrangement/Nicholas Reaction.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4648
_journal_page_last               4651
_journal_paper_doi               10.1021/acs.orglett.7b02274
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C16 H22 O4'
_chemical_formula_sum            'C16 H22 O4'
_chemical_formula_weight         278.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-05-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.074(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4594(19)
_cell_length_b                   9.840(2)
_cell_length_c                   17.995(3)
_cell_measurement_reflns_used    433
_cell_measurement_temperature    271(13)
_cell_measurement_theta_max      26.5340
_cell_measurement_theta_min      3.7980
_cell_volume                     1494.1(5)
_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      271(13)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega -100.00  -61.00   1.5000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  178.0000 -180.0000 26

  2 omega  -85.00  -56.50   1.5000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  178.0000   90.0000 19

  3 omega  -53.00   -5.00   1.5000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000 -120.0000 32

  4 omega   25.00   52.00   1.5000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000 -120.0000 18

  5 omega  -52.00   47.00   1.5000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867    0.0000   90.0000 66
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0808117000
_diffrn_orient_matrix_UB_12      0.0048623000
_diffrn_orient_matrix_UB_13      0.0133348000
_diffrn_orient_matrix_UB_21      -0.0038300000
_diffrn_orient_matrix_UB_22      -0.0663035000
_diffrn_orient_matrix_UB_23      0.0152041000
_diffrn_orient_matrix_UB_31      0.0230952000
_diffrn_orient_matrix_UB_32      -0.0278038000
_diffrn_orient_matrix_UB_33      -0.0339199000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_unetI/netI     0.1558
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5611
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.43
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.08080
_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    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.1990
_refine_ls_R_factor_gt           0.0744
_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^)+(0.0215P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1475
_reflns_number_gt                1129
_reflns_number_total             2924
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b02274_si_003.cif
_cod_data_source_block           shaohui_0507_1
_cod_original_cell_volume        1494.2(6)
_cod_database_code               1547034
_chemical_oxdiff_formula         'C H O'
_reflns_odcompleteness_completeness 99.63
_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:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C11(H11A,
 H11B), C15(H15A,H15B)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
2.d :
 C13(H13)
;
_olex2_date_sample_data_collection 2017-05-08
_olex2_submission_special_instructions 'No special instructions were received'