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_7115915
_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 H16 Cl N O2'
_chemical_formula_sum            'C20 H16 Cl N O2'
_chemical_formula_weight         337.79
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-06-20
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.18 svn.r2945 for OlexSys, GUI svn.r4846)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.8439(4)
_cell_length_b                   11.8914(2)
_cell_length_c                   22.4284(6)
_cell_measurement_reflns_used    10048
_cell_measurement_temperature    99.99(13)
_cell_measurement_theta_max      30.4500
_cell_measurement_theta_min      1.8200
_cell_volume                     3158.83(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details
;
  1 omega  -67.00  121.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7803   19.0000  120.0000 188

  2 omega  -73.00   70.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7803  -77.0000   30.0000 143

  3 omega  -15.00  119.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7803   57.0000  -90.0000 134

  4 omega    0.00   37.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -27.7178 -123.0000   55.8240 37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0145428000
_diffrn_orient_matrix_UB_12      -0.0537968000
_diffrn_orient_matrix_UB_13      0.0113045000
_diffrn_orient_matrix_UB_21      0.0083185000
_diffrn_orient_matrix_UB_22      -0.0197581000
_diffrn_orient_matrix_UB_23      -0.0295440000
_diffrn_orient_matrix_UB_31      0.0574303000
_diffrn_orient_matrix_UB_32      0.0164090000
_diffrn_orient_matrix_UB_33      0.0013630000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0849
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            25699
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.078
_diffrn_reflns_theta_min         1.816
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  0.811
_exptl_absorpt_correction_T_min  0.616
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.4067
_exptl_crystal_size_mid          0.2282
_exptl_crystal_size_min          0.1761
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 2467 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         10247
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0597
_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^)+(0.0543P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1417
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.900
_reflns_number_gt                7473
_reflns_number_total             10247
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc06556e2.cif
_cod_data_source_block           exp_2260
_cod_original_cell_volume        3158.84(14)
_cod_database_code               7115915
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C20 H16 N O2 Cl'
_reflns_odcompleteness_completeness 99.97
_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
2. Others
 Sof(Cl3)=Sof(C4B)=Sof(H4B)=Sof(C3B)=Sof(H3B)=Sof(C6B)=Sof(C5B)=Sof(H5B)=
 Sof(C2B)=Sof(H2B)=1-FVAR(1)
 Sof(Cl1)=Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(C4A)=Sof(H4A)=Sof(C2A)=Sof(H2A)=
 Sof(C3A)=Sof(H3A)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C27(H27), C32(H32), C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C34(H34A,H34B), C14(H14A,H14B), C13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C39(H39), C37(H37), C22(H22), C24(H24), C25(H25), C38(H38), C40(H40),
 C23(H23), C29(H29), C30(H30), C9(H9), C18(H18), C20(H20), C10(H10), C17(H17),
 C19(H19), C5A(H5A), C4A(H4A), C2A(H2A), C3A(H3A), C4B(H4B), C3B(H3B), C5B(H5B),
  C2B(H2B)
;
_olex2_submission_special_instructions 'No special instructions were received'