Enantioselective Synthesis of Tetrahydropyridines/Piperidines via Stepwise [4 + 2]/[2 + 2] Cyclizations.
Wang, Zhen; Xu, Huacheng; Su, Qin; Hu, Ping; Shao, Pan-Lin; He, Yun; Lu, Yixin; Organic letters 19 (2017) 3111–3114; doi:10.1021/acs.orglett.7b01221

data_1556051
_publ_section_title
;
 Enantioselective Synthesis of Tetrahydropyridines/Piperidines via
 Stepwise [4 + 2]/[2 + 2] Cyclizations.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3111
_journal_page_last               3114
_journal_paper_doi               10.1021/acs.orglett.7b01221
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C33 H26 Cl N O4 S'
_chemical_formula_sum            'C33 H26 Cl N O4 S'
_chemical_formula_weight         568.06
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-09-08
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9355(5)
_cell_length_b                   14.8690(6)
_cell_length_c                   20.8047(11)
_cell_measurement_reflns_used    2649
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.2980
_cell_measurement_theta_min      3.7010
_cell_volume                     2764.2(2)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   -4.00   22.60   0.7000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000 -150.0000 38

  2 omega  -46.00   77.20   0.7000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856    0.0000  -30.0000 176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0238061000
_diffrn_orient_matrix_UB_12      -0.0125221000
_diffrn_orient_matrix_UB_13      -0.0312783000
_diffrn_orient_matrix_UB_21      -0.0731909000
_diffrn_orient_matrix_UB_22      -0.0155567000
_diffrn_orient_matrix_UB_23      -0.0070772000
_diffrn_orient_matrix_UB_31      -0.0194299000
_diffrn_orient_matrix_UB_32      0.0433300000
_diffrn_orient_matrix_UB_33      -0.0115580000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9007
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         3.005
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22828
_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_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1525 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         5422
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0507P)^2^+0.1698P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1099
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_full    0.933
_reflns_Friedel_fraction_max     0.911
_reflns_number_gt                4408
_reflns_number_total             5422
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01221_si_002.cif
_cod_data_source_block           160907_s1_wz
_cod_original_cell_volume        2764.1(2)
_cod_database_code               1556051
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         c12h12n2o3cl1s1
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.905
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16),
 C22(H22), C23(H23), C25(H25), C26(H26), C28(H28), C29(H29), C31(H31), C32(H32)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C33(H33A,H33B,H33C)
;
_shelx_res_checksum              23444
_shelx_hkl_checksum              27666
_olex2_submission_special_instructions 'No special instructions were received'