Asymmetric Total Synthesis of (-)-Lycospidine A.
Xu, Shiyan; Zhang, Jing; Ma, Donghui; Xu, Dengyu; Xie, Xingang; She, Xuegong; Organic letters 18 (2016) 4682–4685; doi:10.1021/acs.orglett.6b02322

data_1555741
_publ_section_title
;
 Asymmetric Total Synthesis of (-)-Lycospidine A.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4682
_journal_page_last               4685
_journal_paper_doi               10.1021/acs.orglett.6b02322
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H23 N O3'
_chemical_formula_sum            'C15 H23 N O3'
_chemical_formula_weight         265.34
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-07-27
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5731(5)
_cell_length_b                   9.2969(4)
_cell_length_c                   17.1079(7)
_cell_measurement_reflns_used    925
_cell_measurement_temperature    294.23(10)
_cell_measurement_theta_max      23.7830
_cell_measurement_theta_min      4.0110
_cell_volume                     1363.56(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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_environment      air
_diffrn_ambient_temperature      294.23(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -38.00   85.25   1.4500    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867    0.0000  150.0000 85

  2 omega   64.00   91.55   1.4500    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000  -30.0000 19
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0360413000
_diffrn_orient_matrix_UB_12      -0.0134817000
_diffrn_orient_matrix_UB_13      0.0365842000
_diffrn_orient_matrix_UB_21      0.0681343000
_diffrn_orient_matrix_UB_22      -0.0361898000
_diffrn_orient_matrix_UB_23      0.0129219000
_diffrn_orient_matrix_UB_31      0.0300506000
_diffrn_orient_matrix_UB_32      0.0658036000
_diffrn_orient_matrix_UB_33      0.0146152000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3496
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.017
_diffrn_reflns_theta_min         3.364
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.293
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 575 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.6(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2540
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0532
_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^)+(0.0325P)^2^+0.1623P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1118
_reflns_Friedel_coverage         0.627
_reflns_Friedel_fraction_full    0.884
_reflns_Friedel_fraction_max     0.872
_reflns_number_gt                1994
_reflns_number_total             2540
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02322_si_004.cif
_cod_data_source_block           xushy_0722_1
_cod_original_cell_volume        1363.55(12)
_cod_database_code               1555741
_reflns_odcompleteness_completeness 99.51
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C12(H12A,H12B), C14(H14A,
 H14B)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-07-25
_olex2_submission_special_instructions 'No special instructions were received'