#------------------------------------------------------------------------------
#$Date: 2016-03-22 14:06:56 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178985 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/08/4120894.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_4120894
loop_
_publ_author_name
'Arvind Jaganathan'
'Richard J. Staples'
'Babak Borhan'
_publ_section_title
;
 Kinetic Resolution of Unsaturated Amides in a Chlorocyclization Reaction:
 Concomitant Enantiomer Differentiation and Face Selective Alkene
 Chlorination by a Single Catalyst
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14806
_journal_page_last               14813
_journal_paper_doi               10.1021/ja407241d
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H16 Cl N O'
_chemical_formula_sum            'C17 H16 Cl N O'
_chemical_formula_weight         285.76
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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_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                   5.0927(2)
_cell_length_b                   10.4944(3)
_cell_length_c                   26.6942(8)
_cell_measurement_reflns_used    961
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      65.23
_cell_measurement_theta_min      5.36
_cell_volume                     1426.67(8)
_computing_cell_refinement       'APEX2 (BRUKER, V2008.5-0, 2006)'
_computing_data_collection       'COSMO (BRUKER, V1.58, 2006)'
_computing_data_reduction        'SAINT (BRUKER, V7.34A, 2006)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_publication_material
'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_refinement
'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_solution
'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω,and/f 0.5 deg'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_sigmaI/netI    0.0536
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            6336
_diffrn_reflns_theta_full        67.87
_diffrn_reflns_theta_max         67.87
_diffrn_reflns_theta_min         3.31
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.315
_exptl_absorpt_correction_T_max  0.8679
_exptl_absorpt_correction_T_min  0.4105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.004(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0331
_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/[σ²(Fo²)+(0.0261P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0750
_reflns_number_gt                2239
_reflns_number_total             2468
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja407241d_si_003.cif
_cod_data_source_block           bb76_0m
_cod_database_code               4120894
#BEGIN Tags that were not found in dictionaries:
_contact_crystallographer_name   'Richard Staples'
_contact_crystallographer_email  staples@chemistry.msu.com
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
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
Cl1 Cl 0.41832(12) 1.06288(5) 0.978614(19) 0.03815(14) Uani 1 1 d .
O1 O 0.7721(3) 0.96616(14) 0.85070(5) 0.0295(3) Uani 1 1 d .
N1 N 0.8949(4) 1.17900(17) 0.86615(6) 0.0299(4) Uani 1 1 d .
C1 C 0.7338(4) 1.1871(2) 0.91178(8) 0.0299(4) Uani 1 1 d .
H1 H 0.8546 1.1849 0.9413 0.036 Uiso 1 1 calc R
C2 C 0.5462(4) 1.0737(2) 0.91603(7) 0.0262(4) Uani 1 1 d .
H2 H 0.3966 1.0869 0.8923 0.031 Uiso 1 1 calc R
C3 C 0.6876(4) 0.9509(2) 0.90198(7) 0.0265(4) Uani 1 1 d .
H3 H 0.8447 0.9398 0.9240 0.032 Uiso 1 1 calc R
C4 C 0.8980(4) 1.07826(19) 0.83999(7) 0.0264(4) Uani 1 1 d .
C5 C 0.5896(5) 1.3133(2) 0.91246(8) 0.0363(5) Uani 1 1 d .
H5A H 0.7166 1.3831 0.9097 0.054 Uiso 1 1 calc R
H5B H 0.4920 1.3215 0.9439 0.054 Uiso 1 1 calc R
H5C H 0.4670 1.3169 0.8842 0.054 Uiso 1 1 calc R
C6 C 0.5212(4) 0.8326(2) 0.90413(8) 0.0259(4) Uani 1 1 d .
C7 C 0.5639(5) 0.7414(2) 0.94129(8) 0.0324(5) Uani 1 1 d .
H7 H 0.7011 0.7529 0.9650 0.039 Uiso 1 1 calc R
C8 C 0.4059(5) 0.6340(2) 0.94359(9) 0.0378(5) Uani 1 1 d .
H8 H 0.4347 0.5721 0.9690 0.045 Uiso 1 1 calc R
C9 C 0.2066(5) 0.6165(2) 0.90916(10) 0.0403(6) Uani 1 1 d .
H9 H 0.0982 0.5429 0.9109 0.048 Uiso 1 1 calc R
C10 C 0.1658(4) 0.7062(2) 0.87226(10) 0.0374(5) Uani 1 1 d .
H10 H 0.0290 0.6943 0.8485 0.045 Uiso 1 1 calc R
C11 C 0.3234(4) 0.8137(2) 0.86961(9) 0.0316(5) Uani 1 1 d .
H11 H 0.2950 0.8746 0.8439 0.038 Uiso 1 1 calc R
C12 C 1.0514(4) 1.0686(2) 0.79296(7) 0.0266(4) Uani 1 1 d .
C13 C 1.0169(4) 0.9668(2) 0.76036(8) 0.0319(5) Uani 1 1 d .
H13 H 0.8882 0.9038 0.7675 0.038 Uiso 1 1 calc R
C14 C 1.1693(5) 0.9564(2) 0.71751(8) 0.0355(5) Uani 1 1 d .
H14 H 1.1431 0.8870 0.6952 0.043 Uiso 1 1 calc R
C15 C 1.3587(4) 1.0467(2) 0.70711(8) 0.0375(5) Uani 1 1 d .
H15 H 1.4640 1.0390 0.6779 0.045 Uiso 1 1 calc R
C16 C 1.3947(5) 1.1487(2) 0.73955(9) 0.0350(5) Uani 1 1 d .
H16 H 1.5252 1.2108 0.7325 0.042 Uiso 1 1 calc R
C17 C 1.2411(4) 1.1600(2) 0.78205(8) 0.0305(5) Uani 1 1 d .
H17 H 1.2652 1.2305 0.8039 0.037 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C4 O1 C3 115.64(15)
C4 N1 C1 120.75(18)
N1 C1 C5 109.30(17)
N1 C1 C2 111.41(16)
C5 C1 C2 112.10(19)
N1 C1 H1 108.0
C5 C1 H1 108.0
C2 C1 H1 108.0
C3 C2 C1 110.14(16)
C3 C2 Cl1 110.27(14)
C1 C2 Cl1 110.16(14)
C3 C2 H2 108.7
C1 C2 H2 108.7
Cl1 C2 H2 108.7
O1 C3 C6 107.20(16)
O1 C3 C2 106.29(15)
C6 C3 C2 115.00(16)
O1 C3 H3 109.4
C6 C3 H3 109.4
C2 C3 H3 109.4
N1 C4 O1 126.56(18)
N1 C4 C12 122.05(19)
O1 C4 C12 111.38(16)
C1 C5 H5A 109.5
C1 C5 H5B 109.5
H5A C5 H5B 109.5
C1 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C11 C6 C7 119.3(2)
C11 C6 C3 120.34(19)
C7 C6 C3 120.35(19)
C8 C7 C6 119.9(2)
C8 C7 H7 120.0
C6 C7 H7 120.0
C9 C8 C7 120.3(2)
C9 C8 H8 119.8
C7 C8 H8 119.8
C10 C9 C8 119.7(2)
C10 C9 H9 120.2
C8 C9 H9 120.2
C9 C10 C11 120.3(2)
C9 C10 H10 119.8
C11 C10 H10 119.8
C6 C11 C10 120.4(2)
C6 C11 H11 119.8
C10 C11 H11 119.8
C13 C12 C17 119.11(19)
C13 C12 C4 121.12(18)
C17 C12 C4 119.71(19)
C14 C13 C12 120.4(2)
C14 C13 H13 119.8
C12 C13 H13 119.8
C15 C14 C13 120.2(2)
C15 C14 H14 119.9
C13 C14 H14 119.9
C14 C15 C16 119.7(2)
C14 C15 H15 120.1
C16 C15 H15 120.1
C17 C16 C15 120.2(2)
C17 C16 H16 119.9
C15 C16 H16 119.9
C16 C17 C12 120.3(2)
C16 C17 H17 119.8
C12 C17 H17 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C2 1.7967(19)
O1 C4 1.370(3)
O1 C3 1.444(2)
N1 C4 1.267(3)
N1 C1 1.471(3)
C1 C5 1.515(3)
C1 C2 1.530(3)
C1 H1 1.0000
C2 C3 1.523(3)
C2 H2 1.0000
C3 C6 1.504(3)
C3 H3 1.0000
C4 C12 1.482(3)
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
C6 C11 1.380(3)
C6 C7 1.396(3)
C7 C8 1.387(3)
C7 H7 0.9500
C8 C9 1.382(4)
C8 H8 0.9500
C9 C10 1.378(4)
C9 H9 0.9500
C10 C11 1.386(3)
C10 H10 0.9500
C11 H11 0.9500
C12 C13 1.389(3)
C12 C17 1.392(3)
C13 C14 1.386(3)
C13 H13 0.9500
C14 C15 1.380(3)
C14 H14 0.9500
C15 C16 1.389(4)
C15 H15 0.9500
C16 C17 1.383(3)
C16 H16 0.9500
C17 H17 0.9500
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C4 N1 C1 C5 -135.0(2)
C4 N1 C1 C2 -10.6(3)
N1 C1 C2 C3 42.8(2)
C5 C1 C2 C3 165.60(17)
N1 C1 C2 Cl1 164.61(14)
C5 C1 C2 Cl1 -72.54(19)
C4 O1 C3 C6 171.78(16)
C4 O1 C3 C2 48.3(2)
C1 C2 C3 O1 -60.8(2)
Cl1 C2 C3 O1 177.40(13)
C1 C2 C3 C6 -179.25(17)
Cl1 C2 C3 C6 59.0(2)
C1 N1 C4 O1 -3.6(3)
C1 N1 C4 C12 177.97(18)
C3 O1 C4 N1 -17.3(3)
C3 O1 C4 C12 161.24(16)
O1 C3 C6 C11 -48.3(2)
C2 C3 C6 C11 69.6(2)
O1 C3 C6 C7 132.22(19)
C2 C3 C6 C7 -109.9(2)
C11 C6 C7 C8 -0.9(3)
C3 C6 C7 C8 178.6(2)
C6 C7 C8 C9 0.2(3)
C7 C8 C9 C10 0.2(4)
C8 C9 C10 C11 0.0(4)
C7 C6 C11 C10 1.1(3)
C3 C6 C11 C10 -178.5(2)
C9 C10 C11 C6 -0.6(3)
N1 C4 C12 C13 -168.5(2)
O1 C4 C12 C13 12.8(3)
N1 C4 C12 C17 14.1(3)
O1 C4 C12 C17 -164.50(18)
C17 C12 C13 C14 -0.1(3)
C4 C12 C13 C14 -177.43(19)
C12 C13 C14 C15 0.7(3)
C13 C14 C15 C16 -0.6(3)
C14 C15 C16 C17 -0.1(3)
C15 C16 C17 C12 0.7(3)
C13 C12 C17 C16 -0.6(3)
C4 C12 C17 C16 176.8(2)
