Organocatalytic asymmetric strategies to carbocyclic structures by gamma-alkylation-annulation sequences
Bjarke S. Donslund; Kim Soholm Halskov; Lars A. Leth; Bruno Matos Paz; Karl Anker Jorgensen; Chem.Commun. 50 (2014) 13676–; doi:10.1039/C4cc06556E

data_7115914
_publ_section_title
;
 Organocatalytic asymmetric strategies to carbocyclic structures by
 gamma-alkylation-annulation sequences
;
_journal_name_full               Chem.Commun.
_journal_page_first              13676
_journal_paper_doi               10.1039/C4cc06556E
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H18 O2 S'
_chemical_formula_sum            'C20 H18 O2 S'
_chemical_formula_weight         322.40
_chemical_name_common            2013_06_26
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-06-28
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                103.126(5)
_cell_angle_beta                 98.144(7)
_cell_angle_gamma                98.902(5)
_cell_formula_units_Z            2
_cell_length_a                   8.0288(16)
_cell_length_b                   9.2244(19)
_cell_length_c                   11.460(3)
_cell_measurement_reflns_used    9945
_cell_measurement_temperature    100
_cell_measurement_theta_max      21.93
_cell_measurement_theta_min      2.30
_cell_volume                     802.7(3)
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            36305
_diffrn_reflns_theta_full        21.95
_diffrn_reflns_theta_max         21.95
_diffrn_reflns_theta_min         1.46
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1306 before and 0.0568 after correction.
The Ratio of minimum to maximum transmission is 0.7902.
The \l/2 correction factor is 0.0015.
;
_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    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.07(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         7505
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0563
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0305P)^2^+1.4036P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1354
_reflns_number_gt                6054
_reflns_number_total             7505
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc06556e2.cif
_cod_data_source_block           2013_06_26
_cod_database_code               7115914
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C29(H29), C36(H36)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C24(H24A,H24B), C26(H26A,H26B), C32(H32A,H32B), C37(H37A,
 H37B), C43(H43A,H43B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C15(H15), C17(H17), C18(H18), C19(H19),
 C21(H21), C23(H23), C25(H25), C27(H27), C28(H28), C30(H30), C31(H31), C35(H35),
  C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C1(H1), C2(H2)
;