#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:09:00 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180170 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/66/7106602.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7106602
loop_
_publ_author_name
'Wentao Wang'
'Xiangjin Lian'
'Donghui Chen'
'Xiaohua Liu'
'Lili Lin'
'Xiaoming Feng'
_publ_section_title
;
 Highly enantioselective yttrium(III)-catalyzed Friedel-Crafts alkylation
 of B-trichloro(trifluoro)methyl aryl enones with indoles
;
_journal_name_full               Chem.Commun.
_journal_page_first              7821
_journal_paper_doi               10.1039/c1cc12306h
_journal_volume                  47
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H14 Cl3 N O'
_chemical_formula_sum            'C18 H14 Cl3 N O'
_chemical_formula_weight         366.65
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.6727(8)
_cell_length_b                   14.1660(7)
_cell_length_c                   5.9443(2)
_cell_measurement_reflns_used    1741
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.7862
_cell_measurement_theta_min      3.0506
_cell_volume                     1656.58(12)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_molecular_graphics
;
OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material
;
OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., 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      293(2)
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
1 omega -87.00 9.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- -16.7361 -38.0000 30.0000 96

2 omega -41.00 16.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- -16.7361 77.0000 -180.0000 57
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0175074
_diffrn_orient_matrix_UB_12      0.0423529
_diffrn_orient_matrix_UB_13      0.0264195
_diffrn_orient_matrix_UB_21      0.0314794
_diffrn_orient_matrix_UB_22      0.0229204
_diffrn_orient_matrix_UB_23      0.0199368
_diffrn_orient_matrix_UB_31      0.0014517
_diffrn_orient_matrix_UB_32      0.0137413
_diffrn_orient_matrix_UB_33      -0.1146407
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5029
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    0.556
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.99371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0440
_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/[σ²(Fo²)+(0.0240P)²+0.0210P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0685
_refine_ls_wR_factor_ref         0.0752
_reflns_number_gt                2497
_reflns_number_total             3111
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc12306h.txt
_cod_data_source_block           110107_S2_WWT
_cod_original_cell_volume        1656.56(13)
_cod_database_code               7106602
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, z'
3 'x+1/2, -y+1/2, -z'
4 '-x+1/2, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.01163(4) 0.86623(6) 0.25058(19) 0.0670(3) Uani 1 1 d . . .
Cl2 Cl 0.06601(5) 0.80593(8) 0.63251(13) 0.0686(3) Uani 1 1 d . . .
Cl3 Cl 0.12899(4) 0.81912(7) 0.19742(15) 0.0583(3) Uani 1 1 d . . .
O1 O 0.11806(11) 0.58554(19) -0.0427(3) 0.0596(7) Uani 1 1 d . . .
N1 N -0.09959(14) 0.5908(2) 0.6627(5) 0.0446(8) Uani 1 1 d . . .
C1 C -0.14114(14) 0.6216(2) 0.4927(5) 0.0374(7) Uani 1 1 d . . .
C2 C -0.09934(13) 0.6620(2) 0.3266(4) 0.0330(7) Uani 1 1 d . . .
C3 C -0.12985(15) 0.6977(2) 0.1329(5) 0.0415(8) Uani 1 1 d . . .
C4 C -0.19945(16) 0.6936(3) 0.1128(6) 0.0504(9) Uani 1 1 d . . .
C5 C -0.23942(17) 0.6541(2) 0.2802(7) 0.0537(10) Uani 1 1 d . . .
C6 C -0.21166(17) 0.6181(3) 0.4724(6) 0.0485(9) Uani 1 1 d . . .
C7 C -0.03072(14) 0.6546(2) 0.4069(4) 0.0333(7) Uani 1 1 d . . .
C8 C -0.03369(16) 0.6117(2) 0.6112(5) 0.0400(8) Uani 1 1 d . . .
C9 C 0.03360(13) 0.6841(2) 0.2885(5) 0.0343(6) Uani 1 1 d . . .
C10 C 0.05241(14) 0.7872(2) 0.3405(5) 0.0435(8) Uani 1 1 d . . .
C11 C 0.09312(16) 0.6168(3) 0.3377(6) 0.0432(8) Uani 1 1 d . . .
C12 C 0.14167(15) 0.6012(2) 0.1443(5) 0.0412(8) Uani 1 1 d . . .
C13 C 0.21619(14) 0.5976(2) 0.1846(5) 0.0341(7) Uani 1 1 d . . .
C14 C 0.24648(16) 0.6279(3) 0.3810(5) 0.0445(8) Uani 1 1 d . . .
C15 C 0.31629(18) 0.6231(3) 0.4085(6) 0.0582(10) Uani 1 1 d . . .
C16 C 0.35611(19) 0.5855(3) 0.2426(7) 0.0626(10) Uani 1 1 d . . .
C17 C 0.32721(19) 0.5551(3) 0.0464(7) 0.0598(11) Uani 1 1 d . . .
C18 C 0.25768(17) 0.5606(3) 0.0148(6) 0.0458(8) Uani 1 1 d . . .
H5 H -0.2877(13) 0.6497(19) 0.263(5) 0.047(8) Uiso 1 1 d . . .
H9 H 0.0238(10) 0.6834(18) 0.128(4) 0.023(6) Uiso 1 1 d . . .
H4 H -0.2202(13) 0.716(2) -0.015(5) 0.042(9) Uiso 1 1 d . . .
H8 H 0.0034(13) 0.5975(19) 0.706(4) 0.042(9) Uiso 1 1 d . . .
H3 H -0.1039(11) 0.7280(19) 0.031(4) 0.027(8) Uiso 1 1 d . . .
H11B H 0.1160(13) 0.634(2) 0.473(5) 0.040(8) Uiso 1 1 d . . .
H1 H -0.1104(13) 0.568(2) 0.768(5) 0.029(9) Uiso 1 1 d . . .
H14 H 0.2192(13) 0.658(2) 0.501(5) 0.047(9) Uiso 1 1 d . . .
H15 H 0.3373(17) 0.647(3) 0.538(6) 0.077(13) Uiso 1 1 d . . .
H17 H 0.3537(18) 0.531(3) -0.069(6) 0.080(13) Uiso 1 1 d . . .
H6 H -0.2364(14) 0.589(2) 0.590(5) 0.044(9) Uiso 1 1 d . . .
H16 H 0.4043(16) 0.584(2) 0.268(6) 0.073(11) Uiso 1 1 d . . .
H18 H 0.2368(14) 0.543(2) -0.127(5) 0.047(9) Uiso 1 1 d . . .
H11A H 0.0759(16) 0.556(3) 0.374(6) 0.069(12) Uiso 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 C10 Cl2 107.95(18) . . ?
Cl1 C10 Cl3 107.23(16) . . ?
Cl2 C10 Cl3 107.47(16) . . ?
O1 C12 C11 118.5(3) . . ?
O1 C12 C13 120.9(3) . . ?
N1 C1 C2 107.3(2) . . ?
N1 C1 C6 130.3(3) . . ?
N1 C8 H8 123.7(16) . . ?
C1 N1 H1 126(2) . . ?
C1 C2 C7 106.7(2) . . ?
C1 C6 H6 117.6(18) . . ?
C2 C3 H3 119.0(15) . . ?
C2 C7 C9 127.9(2) . . ?
C3 C2 C1 118.4(3) . . ?
C3 C2 C7 134.9(3) . . ?
C3 C4 C5 121.3(3) . . ?
C3 C4 H4 119.9(17) . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H3 121.7(15) . . ?
C4 C5 H5 120.9(17) . . ?
C5 C4 H4 118.8(17) . . ?
C5 C6 C1 117.2(3) . . ?
C5 C6 H6 125.1(18) . . ?
C6 C1 C2 122.4(3) . . ?
C6 C5 C4 121.7(3) . . ?
C6 C5 H5 117.5(17) . . ?
C7 C8 N1 109.8(3) . . ?
C7 C8 H8 126.5(16) . . ?
C7 C9 C10 111.8(2) . . ?
C7 C9 C11 112.3(2) . . ?
C7 C9 H9 106.8(13) . . ?
C8 N1 C1 109.4(3) . . ?
C8 N1 H1 124(2) . . ?
C8 C7 C2 106.8(3) . . ?
C8 C7 C9 125.3(3) . . ?
C9 C10 Cl1 111.66(19) . . ?
C9 C10 Cl2 112.0(2) . . ?
C9 C10 Cl3 110.3(2) . . ?
C9 C11 H11B 111.0(17) . . ?
C9 C11 H11A 109(2) . . ?
C10 C9 C11 111.5(3) . . ?
C10 C9 H9 104.7(16) . . ?
C11 C9 H9 109.3(14) . . ?
C12 C11 C9 115.3(3) . . ?
C12 C11 H11B 112.4(16) . . ?
C12 C11 H11A 106(2) . . ?
C13 C12 C11 120.4(3) . . ?
C13 C14 C15 120.9(3) . . ?
C13 C14 H14 120.8(15) . . ?
C13 C18 H18 118.5(17) . . ?
C14 C13 C12 123.5(3) . . ?
C14 C13 C18 118.4(3) . . ?
C14 C15 H15 121(2) . . ?
C15 C14 H14 118.2(16) . . ?
C15 C16 H16 117(2) . . ?
C16 C15 C14 120.1(4) . . ?
C16 C15 H15 119(2) . . ?
C16 C17 C18 120.7(4) . . ?
C16 C17 H17 121(2) . . ?
C17 C16 C15 120.0(3) . . ?
C17 C16 H16 123(2) . . ?
C17 C18 C13 120.0(4) . . ?
C17 C18 H18 121.4(17) . . ?
C18 C13 C12 118.1(3) . . ?
C18 C17 H17 119(2) . . ?
H11B C11 H11A 102(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C10 1.768(3) . ?
Cl2 C10 1.776(3) . ?
Cl3 C10 1.788(3) . ?
O1 C12 1.225(3) . ?
N1 C1 1.371(4) . ?
N1 C8 1.364(4) . ?
N1 H1 0.73(3) . ?
C1 C2 1.407(4) . ?
C1 C6 1.393(4) . ?
C2 C3 1.394(4) . ?
C2 C7 1.436(4) . ?
C3 C4 1.376(4) . ?
C3 H3 0.90(2) . ?
C4 C5 1.387(5) . ?
C4 H4 0.92(3) . ?
C5 C6 1.365(5) . ?
C5 H5 0.96(2) . ?
C6 H6 0.95(3) . ?
C7 C8 1.359(4) . ?
C7 C9 1.507(4) . ?
C8 H8 0.94(3) . ?
C9 C10 1.538(4) . ?
C9 C11 1.538(4) . ?
C9 H9 0.97(2) . ?
C11 C12 1.511(4) . ?
C11 H11B 0.96(3) . ?
C11 H11A 0.95(4) . ?
C12 C13 1.486(4) . ?
C13 C14 1.379(4) . ?
C13 C18 1.400(4) . ?
C14 C15 1.385(4) . ?
C14 H14 0.99(3) . ?
C15 C16 1.368(5) . ?
C15 H15 0.93(3) . ?
C16 C17 1.367(5) . ?
C16 H16 0.96(3) . ?
C17 C18 1.383(5) . ?
C17 H17 0.92(4) . ?
C18 H18 0.97(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.73(3) 2.46(3) 3.073(4) 143(3) 2_566
