Highly enantioselective Friedel-Crafts alkylation of indoles and pyrrole with beta,gamma-unsaturated alpha-ketoesters catalyzed by heteroarylidene-tethered bis(oxazoline) copper complexes
Lei Liu; Hongli Ma; Yumei Xiao; Fengpei Du; Zhaohai Qin; Nan Li; Bin Fu; Chem.Commun. 48 (2012) 9281–; doi:10.1039/c2cc34803a

data_7108320
_publ_section_title
;
 Highly enantioselective Friedel-Crafts alkylation of indoles and pyrrole
 with beta,gamma-unsaturated alpha-ketoesters catalyzed by
 heteroarylidene-tethered bis(oxazoline) copper complexes
;
_journal_name_full               Chem.Commun.
_journal_page_first              9281
_journal_paper_doi               10.1039/c2cc34803a
_journal_volume                  48
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H14 N2 O3'
_chemical_formula_sum            'C16 H14 N2 O3'
_chemical_formula_weight         282.29
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-05-23
_audit_creation_method
;
Olex2 1.1
(compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8802(12)
_cell_length_b                   10.1254(15)
_cell_length_c                   14.573(2)
_cell_measurement_reflns_used    3124
_cell_measurement_temperature    100.2
_cell_measurement_theta_max      69.6247
_cell_measurement_theta_min      4.3597
_cell_volume                     1457.9(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_diffrn_ambient_temperature      100.2
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
1 omega -45.00 -19.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- -33.5000 37.0000 60.0000 26

2 omega -43.00 -18.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- -33.5000 157.0000 78.0000 25

3 omega -105.00 -18.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- -33.5000 -37.0000 -90.0000 87

4 omega -18.00 73.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- 54.0000 -37.0000 -150.0000 91

5 omega -8.00 54.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- 54.0000 -77.0000 -180.0000 62

6 omega 128.00 170.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 111.0000 120.0000 42

7 omega 119.00 177.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 45.0000 0.0000 58

8 omega 53.00 96.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -45.0000 -150.0000 43

9 omega 110.00 167.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 111.0000 30.0000 57

10 omega 53.00 80.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -45.0000 30.0000 27

11 omega 87.00 120.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 45.0000 -30.0000 33

12 omega 148.00 178.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 45.0000 -30.0000 30

13 omega 134.00 178.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 111.0000 -120.0000 44

14 omega 44.00 89.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -45.0000 90.0000 45

15 omega 46.00 161.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -15.0000 0.0000 115
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1139734000
_diffrn_orient_matrix_UB_12      -0.0750500000
_diffrn_orient_matrix_UB_13      -0.0498311000
_diffrn_orient_matrix_UB_21      -0.0473828000
_diffrn_orient_matrix_UB_22      0.0581636000
_diffrn_orient_matrix_UB_23      -0.0919963000
_diffrn_orient_matrix_UB_31      0.0956280000
_diffrn_orient_matrix_UB_32      0.1186840000
_diffrn_orient_matrix_UB_33      0.0137817000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5232
_diffrn_reflns_theta_full        69.79
_diffrn_reflns_theta_max         69.79
_diffrn_reflns_theta_min         5.32
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.742
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2714
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0515P)^2^+0.2513P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0851
_reflns_number_gt                2649
_reflns_number_total             2714
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc34803a.txt
_cod_data_source_block           exp_602
_cod_database_code               7108320
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97