Total synthesis of indole alkaloid (±)-subincanadine e.
Tian, Jingjing; Du, Qiuchen; Guo, Rui; Li, Yun; Cheng, Bin; Zhai, Hongbin; Organic letters 16 (2014) 3173–3175; doi:10.1021/ol501308p

data_1516343
_publ_section_title
;
 Total synthesis of indole alkaloid (+-)-subincanadine e.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3173
_journal_page_last               3175
_journal_paper_doi               10.1021/ol501308p
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C19 H24 N2 O2'
_chemical_formula_sum            'C19 H24 N2 O2'
_chemical_formula_weight         312.40
_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     iterative
_audit_creation_date             2013-10-30
_audit_creation_method
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Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
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_cell_angle_alpha                90
_cell_angle_beta                 106.292(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7462(17)
_cell_length_b                   11.9167(19)
_cell_length_c                   12.6020(11)
_cell_measurement_reflns_used    2346
_cell_measurement_temperature    294.16(10)
_cell_measurement_theta_max      70.4830
_cell_measurement_theta_min      4.9860
_cell_volume                     1981.4(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      294.16(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9354
_diffrn_measured_fraction_theta_max 0.9891
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0060562000
_diffrn_orient_matrix_UB_12      0.1198077000
_diffrn_orient_matrix_UB_13      0.0437890000
_diffrn_orient_matrix_UB_21      -0.1114456000
_diffrn_orient_matrix_UB_22      0.0082182000
_diffrn_orient_matrix_UB_23      -0.0694004000
_diffrn_orient_matrix_UB_31      -0.0340529000
_diffrn_orient_matrix_UB_32      -0.0481251000
_diffrn_orient_matrix_UB_33      0.0973041000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9857
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.951
_diffrn_reflns_theta_min         3.350
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.541
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81597
_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_density_diffrn    1.047
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2900
_exptl_crystal_size_mid          0.2400
_exptl_crystal_size_min          0.1500
_platon_squeeze_details
;
;
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0022(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3794
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0626
_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^)+(0.1043P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1708
_refine_ls_wR_factor_ref         0.1895
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2657
_reflns_number_total             3794
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol501308p_si_002.cif
_cod_data_source_block           tianjj1028
_cod_depositor_comments          'Adding full bibliography for 1516343.cif.'
_cod_database_code               1516343
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 93.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C15(H15A,H15B), C18(H18A,H18B),
 C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), C2(H2A), C3(H3), C4(H4), C5(H5), C16(H16)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_shelx_res_checksum              2758
_shelx_hkl_checksum              91306