# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
'Ran Jiang'
'Hai-Yan Xu'
'Xiao-ping Xu'
'Xue-Qiang Chu'
'Shun-jun Ji'
_publ_contact_author_name        'Shun-Jun Ji'
_publ_contact_author_email       chemjsj@suda.edu.cn

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 820789'
#TrackingRef '- shelxl.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            1-(1-(4-chlorophenyl)ethyl)pyrrolidin-2-one
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H15 Cl N2 O'
_chemical_formula_sum            'C12 H15 Cl N2 O'
_chemical_formula_weight         238.71

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

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'

_cell_length_a                   11.180(3)
_cell_length_b                   9.4995(18)
_cell_length_c                   12.049(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.894(5)
_cell_angle_gamma                90.00
_cell_volume                     1187.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4774
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.696
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 14.63
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7217
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.51
_reflns_number_total             2692
_reflns_number_gt                2020
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'CrystalStructure 3.7.0'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0812P)^2^+0.0102P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.072(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2692
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1404
_refine_ls_wR_factor_gt          0.1287
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0518(4) 0.0681(4) 0.0545(4) 0.0090(3) 0.0071(3) 0.0141(3)
O1 0.0646(9) 0.0587(9) 0.0389(7) -0.0105(6) 0.0326(7) -0.0141(7)
N1 0.0440(8) 0.0339(8) 0.0336(7) -0.0013(6) 0.0216(7) -0.0008(6)
N2 0.0549(9) 0.0344(8) 0.0294(7) -0.0031(6) 0.0156(7) 0.0054(7)
C1 0.0434(9) 0.0391(10) 0.0323(9) -0.0023(7) 0.0177(8) 0.0011(8)
C2 0.0614(12) 0.0489(12) 0.0459(11) -0.0131(9) 0.0278(10) -0.0150(10)
C3 0.0626(13) 0.0607(14) 0.0558(13) -0.0105(10) 0.0375(11) -0.0202(11)
C4 0.0621(12) 0.0483(12) 0.0438(11) -0.0065(8) 0.0340(10) -0.0119(9)
C5 0.0428(9) 0.0333(9) 0.0340(9) 0.0003(7) 0.0196(8) 0.0005(7)
C6 0.0438(10) 0.0448(11) 0.0397(10) -0.0002(8) 0.0142(8) 0.0048(8)
C7 0.0431(9) 0.0283(9) 0.0316(8) -0.0027(7) 0.0144(7) -0.0047(7)
C8 0.0559(11) 0.0468(11) 0.0348(9) 0.0010(8) 0.0215(9) 0.0100(9)
C9 0.0561(11) 0.0493(12) 0.0341(10) 0.0040(8) 0.0188(9) 0.0033(9)
C10 0.0389(9) 0.0401(10) 0.0411(10) 0.0035(8) 0.0092(8) 0.0005(8)
C11 0.0383(10) 0.0432(10) 0.0462(11) -0.0063(8) 0.0175(8) -0.0021(8)
C12 0.0444(10) 0.0421(10) 0.0343(9) -0.0057(8) 0.0174(8) -0.0053(8)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.091