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_1555743
_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 H21 N O3'
_chemical_formula_sum            'C15 H21 N O3'
_chemical_formula_weight         263.33
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-08-20
_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            8
_cell_length_a                   8.4853(3)
_cell_length_b                   8.4853(3)
_cell_length_c                   37.1900(15)
_cell_measurement_reflns_used    1653
_cell_measurement_temperature    294.44(10)
_cell_measurement_theta_max      23.8830
_cell_measurement_theta_min      3.5550
_cell_volume                     2677.69(17)
_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      294.44(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 0.954
_diffrn_measurement_details
;
  1 omega   34.00   97.65   0.9500    3.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9327 -178.0000  150.0000 67

  2 omega   51.00   92.80   0.9500    3.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9327  178.0000  -60.0000 44

  3 omega   28.00   88.80   0.9500    3.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9327   77.0000 -120.0000 64

  4 omega  -65.00  -39.35   0.9500    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.1983  101.0000  151.0000 27
;
_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      0.0666240000
_diffrn_orient_matrix_UB_12      -0.0487430000
_diffrn_orient_matrix_UB_13      0.0030175000
_diffrn_orient_matrix_UB_21      0.0251669000
_diffrn_orient_matrix_UB_22      0.0130640000
_diffrn_orient_matrix_UB_23      -0.0179455000
_diffrn_orient_matrix_UB_31      0.0437656000
_diffrn_orient_matrix_UB_32      0.0666289000
_diffrn_orient_matrix_UB_33      0.0057191000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            8118
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.078
_diffrn_reflns_theta_min         3.250
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93230
_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    1.306
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3043
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0552
_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^)+(0.0482P)^2^+0.3289P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1274
_reflns_Friedel_coverage         0.630
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                2247
_reflns_number_total             3043
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02322_si_003.cif
_cod_data_source_block           xushy_0726
_cod_original_cell_volume        2677.7(2)
_cod_database_code               1555743
_chemical_oxdiff_formula         'C H N O'
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1(2) 0(2)
2. 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
3.a Riding coordinates:
 O2(H2)
3.b Ternary CH refined with riding coordinates:
 C4(H4), C7(H7), C9(H9)
3.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C8(H8A,H8B), C10(H10A,H10B), C13(H13A,
 H13B), C14(H14A,H14B)
3.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-07-26
_olex2_submission_special_instructions 'No special instructions were received'