#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/19/7151948.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_7151948
loop_
_publ_author_name
'Jiang, Ran'
'Xu, Hai-Yan'
'Xu, Xiao-Ping'
'Chu, Xue-Qiang'
'Ji, Shun-Jun'
_publ_section_title
;
 Direct alkylation of indoles and amines by tert-enamides: facile
 access to pharmaceutically active 2-oxo-1-pyrrolidine analogues.
;
_journal_issue                   16
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5659
_journal_page_last               5669
_journal_paper_doi               10.1039/c1ob05546a
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C12 H15 Cl N2 O'
_chemical_formula_sum            'C12 H15 Cl N2 O'
_chemical_formula_weight         238.71
_chemical_name_common            1-(1-(4-chlorophenyl)ethyl)pyrrolidin-2-one
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 111.894(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.180(3)
_cell_length_b                   9.4995(18)
_cell_length_c                   12.049(3)
_cell_measurement_reflns_used    4774
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     1187.4(5)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean 14.63
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7217
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.302
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       0.072(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2692
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0529
_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)+(0.0812P)²+0.0102P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1404
_reflns_number_gt                2020
_reflns_number_total             2692
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob05546a.txt
_cod_data_source_block           shelxl
_cod_original_cell_volume        1187.4(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7151948
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.02937(5) -0.23856(7) 0.72719(5) 0.0618(2) Uani 1 1 d . . .
O1 O 0.60091(14) 0.36868(15) 0.61913(12) 0.0502(4) Uani 1 1 d . . .
N1 N 0.64351(14) 0.32801(15) 0.45054(13) 0.0352(4) Uani 1 1 d . . .
N2 N 0.61414(15) 0.09304(16) 0.37101(13) 0.0396(4) Uani 1 1 d . . .
H2 H 0.5878 0.0643 0.2972 0.048 Uiso 1 1 calc R . .
C1 C 0.65576(18) 0.39861(19) 0.55098(16) 0.0372(4) Uani 1 1 d . . .
C2 C 0.7455(2) 0.5218(2) 0.56246(19) 0.0498(5) Uani 1 1 d . . .
H2A H 0.8094 0.5292 0.6442 0.060 Uiso 1 1 calc R . .
H2B H 0.6972 0.6103 0.5412 0.060 Uiso 1 1 calc R . .
C3 C 0.8098(2) 0.4880(3) 0.4747(2) 0.0552(6) Uani 1 1 d . . .
H3A H 0.8915 0.4385 0.5145 0.066 Uiso 1 1 calc R . .
H3B H 0.8260 0.5739 0.4375 0.066 Uiso 1 1 calc R . .
C4 C 0.7122(2) 0.3939(2) 0.38229(18) 0.0473(5) Uani 1 1 d . . .
H4A H 0.6536 0.4494 0.3156 0.057 Uiso 1 1 calc R . .
H4B H 0.7555 0.3233 0.3511 0.057 Uiso 1 1 calc R . .
C5 C 0.55189(17) 0.21310(18) 0.40018(15) 0.0352(4) Uani 1 1 d . . .
H5 H 0.5170 0.1835 0.4609 0.042 Uiso 1 1 calc R . .
C6 C 0.44061(19) 0.2612(2) 0.28990(17) 0.0432(4) Uani 1 1 d . . .
H6A H 0.4706 0.2755 0.2248 0.065 Uiso 1 1 calc R . .
H6B H 0.4064 0.3489 0.3070 0.065 Uiso 1 1 calc R . .
H6C H 0.3735 0.1901 0.2672 0.065 Uiso 1 1 calc R . .
C7 C 0.71429(17) 0.02264(18) 0.45697(15) 0.0342(4) Uani 1 1 d . . .
C8 C 0.73134(19) 0.0217(2) 0.57810(16) 0.0445(5) Uani 1 1 d . . .
H8 H 0.6764 0.0757 0.6042 0.053 Uiso 1 1 calc R . .
C9 C 0.82765(18) -0.0576(2) 0.65956(17) 0.0459(5) Uani 1 1 d . . .
H9 H 0.8371 -0.0582 0.7404 0.055 Uiso 1 1 calc R . .
C10 C 0.91023(18) -0.1359(2) 0.62303(17) 0.0417(4) Uani 1 1 d . . .
C11 C 0.89877(17) -0.1328(2) 0.50501(17) 0.0421(4) Uani 1 1 d . . .
H11 H 0.9566 -0.1839 0.4804 0.050 Uiso 1 1 calc R . .
C12 C 0.80217(17) -0.0545(2) 0.42367(16) 0.0395(4) Uani 1 1 d . . .
H12 H 0.7950 -0.0528 0.3434 0.047 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 0.0033 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'
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'
Cl Cl 0.1484 0.1585 '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
C1 N1 C4 113.25(15) . . ?
C1 N1 C5 124.41(14) . . ?
C4 N1 C5 121.34(14) . . ?
C7 N2 C5 121.91(14) . . ?
C7 N2 H2 119.0 . . ?
C5 N2 H2 119.0 . . ?
O1 C1 N1 125.29(17) . . ?
O1 C1 C2 126.67(16) . . ?
N1 C1 C2 108.02(14) . . ?
C1 C2 C3 104.03(16) . . ?
C1 C2 H2A 110.9 . . ?
C3 C2 H2A 110.9 . . ?
C1 C2 H2B 110.9 . . ?
C3 C2 H2B 110.9 . . ?
H2A C2 H2B 109.0 . . ?
C2 C3 C4 103.74(15) . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
C4 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
N1 C4 C3 102.91(15) . . ?
N1 C4 H4A 111.2 . . ?
C3 C4 H4A 111.2 . . ?
N1 C4 H4B 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
N2 C5 N1 111.28(14) . . ?
N2 C5 C6 109.72(15) . . ?
N1 C5 C6 110.96(15) . . ?
N2 C5 H5 108.3 . . ?
N1 C5 H5 108.3 . . ?
C6 C5 H5 108.3 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 C12 119.88(15) . . ?
N2 C7 C8 122.83(16) . . ?
C12 C7 C8 117.28(17) . . ?
C9 C8 C7 120.83(17) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C9 C8 120.35(17) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.11(18) . . ?
C9 C10 Cl1 119.57(15) . . ?
C11 C10 Cl1 120.32(16) . . ?
C12 C11 C10 119.49(17) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C7 121.87(16) . . ?
C11 C12 H12 119.1 . . ?
C7 C12 H12 119.1 . . ?
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 1.748(2) . ?
O1 C1 1.227(2) . ?
N1 C1 1.345(2) . ?
N1 C4 1.459(2) . ?
N1 C5 1.465(2) . ?
N2 C7 1.382(2) . ?
N2 C5 1.446(2) . ?
N2 H2 0.8700 . ?
C1 C2 1.514(3) . ?
C2 C3 1.518(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C3 C4 1.524(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 C6 1.513(3) . ?
C5 H5 0.9900 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 H6C 0.9700 . ?
C7 C12 1.399(2) . ?
C7 C8 1.400(2) . ?
C8 C9 1.379(3) . ?
C8 H8 0.9400 . ?
C9 C10 1.379(3) . ?
C9 H9 0.9400 . ?
C10 C11 1.380(3) . ?
C11 C12 1.375(3) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 O1 175.48(19) . . . . ?
C5 N1 C1 O1 6.9(3) . . . . ?
C4 N1 C1 C2 -3.1(2) . . . . ?
C5 N1 C1 C2 -171.74(17) . . . . ?
O1 C1 C2 C3 166.5(2) . . . . ?
N1 C1 C2 C3 -15.0(2) . . . . ?
C1 C2 C3 C4 26.0(2) . . . . ?
C1 N1 C4 C3 19.7(2) . . . . ?
C5 N1 C4 C3 -171.28(16) . . . . ?
C2 C3 C4 N1 -27.4(2) . . . . ?
C7 N2 C5 N1 60.7(2) . . . . ?
C7 N2 C5 C6 -176.16(16) . . . . ?
C1 N1 C5 N2 -131.56(17) . . . . ?
C4 N1 C5 N2 60.7(2) . . . . ?
C1 N1 C5 C6 105.96(19) . . . . ?
C4 N1 C5 C6 -61.8(2) . . . . ?
C5 N2 C7 C12 -156.05(16) . . . . ?
C5 N2 C7 C8 25.5(3) . . . . ?
N2 C7 C8 C9 175.70(18) . . . . ?
C12 C7 C8 C9 -2.8(3) . . . . ?
C7 C8 C9 C10 0.9(3) . . . . ?
C8 C9 C10 C11 1.5(3) . . . . ?
C8 C9 C10 Cl1 -178.59(15) . . . . ?
C9 C10 C11 C12 -1.9(3) . . . . ?
Cl1 C10 C11 C12 178.18(14) . . . . ?
C10 C11 C12 C7 -0.1(3) . . . . ?
N2 C7 C12 C11 -176.15(16) . . . . ?
C8 C7 C12 C11 2.4(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26998152
