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_1555742
_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 H19 Cl2 N O2'
_chemical_formula_sum            'C15 H19 Cl2 N O2'
_chemical_formula_weight         316.21
_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_Hall           'P 61'
_space_group_name_H-M_alt        'P 61'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-08-15
_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                120
_cell_formula_units_Z            6
_cell_length_a                   14.6129(6)
_cell_length_b                   14.6129(6)
_cell_length_c                   14.5834(6)
_cell_measurement_reflns_used    2132
_cell_measurement_temperature    290.8(2)
_cell_measurement_theta_max      49.4040
_cell_measurement_theta_min      4.6120
_cell_volume                     2696.88(19)
_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)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.8(2)
_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   -8.00   53.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -60.0000 61

  2 omega   82.00  115.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000    0.0000 33

  3 omega   97.00  122.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000    0.0000 25

  4 omega   91.00  118.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   30.0000 27

  5 omega   68.00  114.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -30.0000 46

  6 omega   78.00  104.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 26

  7 omega  121.00  161.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 40

  8 omega  137.00  164.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   30.0000 27

  9 omega  123.00  177.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000   60.0000 54

 10 omega  108.00  177.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 69

 11 omega  101.00  176.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   60.0000 75

 12 omega  100.00  134.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 34

 13 omega   87.00  115.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000    0.0000 28

 14 omega   88.00  115.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000    0.0000 27

 15 omega   88.00  114.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000   30.0000 26

 16 omega   82.00  108.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000    0.0000 26

 17 omega   87.00  176.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -30.0000 89

 18 omega   84.00  151.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  150.0000 67

 19 omega   78.00  104.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 26

 20 omega   88.00  116.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -30.0000 28

 21 omega   88.00  113.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -60.0000 25

 22 omega   78.00  104.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 26

 23 omega   83.00  109.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   69.0000  -44.1432 26

 24 omega   83.00  108.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  -30.0000 25

 25 omega   82.00  108.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   30.0000 26

 26 omega   78.00  105.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000   60.0000 27

 27 omega   37.00   64.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -30.0000 27

 28 omega   34.00   62.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000    0.0000 28

 29 omega   24.00   68.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000    0.0000 44

 30 omega   50.00   84.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -90.0000 34

 31 omega   61.00   93.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 32

 32 omega    4.00   93.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -101.0000 -105.0000 89

 33 omega    1.00   59.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000 -180.0000 58

 34 omega  -48.00   21.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 69
;
_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      -0.0697277000
_diffrn_orient_matrix_UB_12      0.0405905000
_diffrn_orient_matrix_UB_13      -0.0422016000
_diffrn_orient_matrix_UB_21      0.0929965000
_diffrn_orient_matrix_UB_22      0.1142894000
_diffrn_orient_matrix_UB_23      0.0058953000
_diffrn_orient_matrix_UB_31      0.0361539000
_diffrn_orient_matrix_UB_32      -0.0106856000
_diffrn_orient_matrix_UB_33      -0.0966599000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15695
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.567
_diffrn_reflns_theta_min         4.626
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.253
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62473
_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    1.168
_exptl_crystal_description       block
_exptl_crystal_F_000             996
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 745 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3255
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0595P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1229
_reflns_Friedel_coverage         0.855
_reflns_Friedel_fraction_full    0.941
_reflns_Friedel_fraction_max     0.926
_reflns_number_gt                2200
_reflns_number_total             3255
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02322_si_002.cif
_cod_data_source_block           xushy_00304_sqd
_cod_original_cell_volume        2696.9(3)
_cod_database_code               1555742
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C4(H4), C7(H7), C11(H11), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C10(H10A,H10B), C12(H12A,H12B),
 C14(H14A,H14B)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_platon_squeeze_void_probe_radius 1.20