#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/98/2209810.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2209810
loop_
_publ_author_name
'Ping, Zhang'
'Na, Liu'
'Yuan, Li'
_publ_section_title
4-(4-Chlorophenyl)-3-(2,5-dioxo-2,5-dihydropyrrol-1-yl)-1-(4-methoxyphenyl)azetidin-2-one
_journal_coeditor_code           CS2007
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3523
_journal_page_last               o3524
_journal_paper_doi               10.1107/S1600536806028443
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C20 H15 Cl N2 O4'
_chemical_formula_moiety         'C20 H15 Cl N2 O4'
_chemical_formula_sum            'C20 H15 Cl N2 O4'
_chemical_formula_weight         382.79
_chemical_name_systematic
;
4-(4-Chlorophenyl)-3-(2,5-dioxo-2,5-dihydropyrrol-1-yl)-1-(4-
methoxyphenyl)azetidin-2-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 112.888(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.344(3)
_cell_length_b                   11.609(3)
_cell_length_c                   13.640(3)
_cell_measurement_reflns_used    1323
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.65
_cell_measurement_theta_min      2.58
_cell_volume                     1800.7(8)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0561
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9542
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  0.866
_exptl_absorpt_correction_T_min  0.845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.304
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3173
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0384
_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)+(0.0178P)²+0.6522P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0979
_reflns_number_gt                2008
_reflns_number_total             3173
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cs2007.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2209810
_cod_database_fobs_code          2209810
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Cl Cl1 0.60540(6) 0.11155(7) 1.02026(6) 0.0771(3) Uani d . 1
O O1 0.65512(15) 0.10125(16) 0.53805(13) 0.0681(5) Uani d . 1
O O2 0.91941(15) -0.08896(16) 0.82125(13) 0.0663(5) Uani d . 1
O O3 1.09703(15) 0.03303(16) 0.74384(13) 0.0635(5) Uani d . 1
O O4 1.39353(15) 0.36837(16) 1.17319(13) 0.0731(5) Uani d . 1
N N1 0.81116(15) 0.02833(16) 0.68067(13) 0.0440(5) Uani d . 1
N N2 1.03130(15) 0.18260(16) 0.82416(14) 0.0453(5) Uani d . 1
C C1 0.6955(2) 0.0289(2) 0.60559(17) 0.0482(6) Uani d . 1
C C2 0.6388(2) -0.0741(2) 0.62785(19) 0.0585(7) Uani d . 1
H H2 0.5614 -0.0967 0.5901 0.070 Uiso calc R 1
C C3 0.7158(2) -0.1288(2) 0.70993(19) 0.0592(7) Uani d . 1
H H3 0.7013 -0.1964 0.7394 0.071 Uiso calc R 1
C C4 0.8287(2) -0.0661(2) 0.74788(18) 0.0500(6) Uani d . 1
C C5 0.89280(19) 0.1201(2) 0.69089(17) 0.0473(6) Uani d . 1
H H5 0.8789 0.1546 0.6215 0.057 Uiso calc R 1
C C6 1.0245(2) 0.0968(2) 0.75346(17) 0.0489(6) Uani d . 1
C C7 0.90632(18) 0.2154(2) 0.77637(16) 0.0446(6) Uani d . 1
H H7 0.8951 0.2930 0.7459 0.054 Uiso calc R 1
C C8 0.83633(18) 0.19596(19) 0.84328(16) 0.0413(5) Uani d . 1
C C9 0.7178(2) 0.2247(2) 0.80150(18) 0.0509(6) Uani d . 1
H H9 0.6856 0.2609 0.7356 0.061 Uiso calc R 1
C C10 0.6473(2) 0.2004(2) 0.85592(19) 0.0543(6) Uani d . 1
H H10 0.5679 0.2198 0.8271 0.065 Uiso calc R 1
C C11 0.6955(2) 0.1473(2) 0.95345(19) 0.0490(6) Uani d . 1
C C12 0.8125(2) 0.1201(2) 0.99809(17) 0.0487(6) Uani d . 1
H H12 0.8445 0.0859 1.0650 0.058 Uiso calc R 1
C C13 0.88260(19) 0.14415(19) 0.94243(17) 0.0458(6) Uani d . 1
H H13 0.9620 0.1252 0.9721 0.055 Uiso calc R 1
C C14 1.12358(18) 0.2319(2) 0.91109(16) 0.0432(5) Uani d . 1
C C15 1.10428(19) 0.3325(2) 0.95628(17) 0.0491(6) Uani d . 1
H H15 1.0312 0.3681 0.9273 0.059 Uiso calc R 1
C C16 1.1921(2) 0.3805(2) 1.04386(18) 0.0508(6) Uani d . 1
H H16 1.1779 0.4476 1.0742 0.061 Uiso calc R 1
C C17 1.3009(2) 0.3287(2) 1.08599(17) 0.0513(6) Uani d . 1
C C18 1.3204(2) 0.2281(2) 1.04144(19) 0.0563(7) Uani d . 1
H H18 1.3938 0.1928 1.0706 0.068 Uiso calc R 1
C C19 1.23342(19) 0.1792(2) 0.95482(18) 0.0513(6) Uani d . 1
H H19 1.2477 0.1114 0.9255 0.062 Uiso calc R 1
C C20 1.3799(2) 0.4755(3) 1.2176(2) 0.0778(9) Uani d . 1
H H20A 1.3616 0.5345 1.1642 0.117 Uiso calc R 1
H H20B 1.4517 0.4948 1.2760 0.117 Uiso calc R 1
H H20C 1.3173 0.4697 1.2424 0.117 Uiso calc R 1
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
C17 O4 C20 117.8(2)
C4 N1 C1 109.84(19)
C4 N1 C5 126.68(18)
C1 N1 C5 123.17(19)
C6 N2 C14 134.30(19)
C6 N2 C7 96.31(17)
C14 N2 C7 129.31(19)
O1 C1 N1 124.5(2)
O1 C1 C2 129.5(2)
N1 C1 C2 106.1(2)
C3 C2 C1 108.8(2)
C3 C2 H2 125.6
C1 C2 H2 125.6
C2 C3 C4 109.4(2)
C2 C3 H3 125.3
C4 C3 H3 125.3
O2 C4 N1 125.2(2)
O2 C4 C3 128.9(2)
N1 C4 C3 105.9(2)
N1 C5 C6 118.32(19)
N1 C5 C7 117.61(17)
C6 C5 C7 85.85(16)
N1 C5 H5 111.0
C6 C5 H5 111.0
C7 C5 H5 111.0
O3 C6 N2 132.8(2)
O3 C6 C5 135.7(2)
N2 C6 C5 91.42(18)
N2 C7 C8 116.41(17)
N2 C7 C5 86.40(16)
C8 C7 C5 115.28(18)
N2 C7 H7 112.1
C8 C7 H7 112.1
C5 C7 H7 112.1
C13 C8 C9 118.3(2)
C13 C8 C7 122.96(19)
C9 C8 C7 118.63(19)
C10 C9 C8 121.1(2)
C10 C9 H9 119.4
C8 C9 H9 119.4
C11 C10 C9 119.2(2)
C11 C10 H10 120.4
C9 C10 H10 120.4
C12 C11 C10 121.3(2)
C12 C11 Cl1 119.41(19)
C10 C11 Cl1 119.29(18)
C11 C12 C13 119.1(2)
C11 C12 H12 120.5
C13 C12 H12 120.5
C12 C13 C8 121.0(2)
C12 C13 H13 119.5
C8 C13 H13 119.5
C15 C14 C19 119.2(2)
C15 C14 N2 119.7(2)
C19 C14 N2 121.1(2)
C16 C15 C14 120.9(2)
C16 C15 H15 119.6
C14 C15 H15 119.6
C17 C16 C15 119.6(2)
C17 C16 H16 120.2
C15 C16 H16 120.2
O4 C17 C16 124.4(2)
O4 C17 C18 115.9(2)
C16 C17 C18 119.7(2)
C19 C18 C17 121.1(2)
C19 C18 H18 119.5
C17 C18 H18 119.5
C18 C19 C14 119.5(2)
C18 C19 H19 120.2
C14 C19 H19 120.2
O4 C20 H20A 109.5
O4 C20 H20B 109.5
H20A C20 H20B 109.5
O4 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C11 1.740(2)
O1 C1 1.203(3)
O2 C4 1.206(3)
O3 C6 1.207(3)
O4 C17 1.370(3)
O4 C20 1.422(3)
N1 C4 1.391(3)
N1 C1 1.396(3)
N1 C5 1.435(3)
N2 C6 1.366(3)
N2 C14 1.407(3)
N2 C7 1.472(3)
C1 C2 1.475(3)
C2 C3 1.316(3)
C2 H2 0.9300
C3 C4 1.476(3)
C3 H3 0.9300
C5 C6 1.538(3)
C5 C7 1.568(3)
C5 H5 0.9800
C7 C8 1.498(3)
C7 H7 0.9800
C8 C13 1.384(3)
C8 C9 1.388(3)
C9 C10 1.375(3)
C9 H9 0.9300
C10 C11 1.374(3)
C10 H10 0.9300
C11 C12 1.368(3)
C12 C13 1.383(3)
C12 H12 0.9300
C13 H13 0.9300
C14 C15 1.383(3)
C14 C19 1.392(3)
C15 C16 1.381(3)
C15 H15 0.9300
C16 C17 1.376(3)
C16 H16 0.9300
C17 C18 1.381(3)
C18 C19 1.373(3)
C18 H18 0.9300
C19 H19 0.9300
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
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 O1 179.2(2)
C5 N1 C1 O1 5.2(3)
C4 N1 C1 C2 -0.9(2)
C5 N1 C1 C2 -174.86(19)
O1 C1 C2 C3 -179.5(2)
N1 C1 C2 C3 0.5(3)
C1 C2 C3 C4 0.0(3)
C1 N1 C4 O2 -179.2(2)
C5 N1 C4 O2 -5.5(4)
C1 N1 C4 C3 0.9(2)
C5 N1 C4 C3 174.6(2)
C2 C3 C4 O2 179.6(3)
C2 C3 C4 N1 -0.5(3)
C4 N1 C5 C6 23.5(3)
C1 N1 C5 C6 -163.58(19)
C4 N1 C5 C7 -77.4(3)
C1 N1 C5 C7 95.5(2)
C14 N2 C6 O3 1.4(4)
C7 N2 C6 O3 178.4(3)
C14 N2 C6 C5 -175.7(2)
C7 N2 C6 C5 1.27(17)
N1 C5 C6 O3 62.6(4)
C7 C5 C6 O3 -178.1(3)
N1 C5 C6 N2 -120.4(2)
C7 C5 C6 N2 -1.19(16)
C6 N2 C7 C8 115.3(2)
C14 N2 C7 C8 -67.6(3)
C6 N2 C7 C5 -1.25(17)
C14 N2 C7 C5 175.9(2)
N1 C5 C7 N2 121.02(19)
C6 C5 C7 N2 1.10(15)
N1 C5 C7 C8 3.4(3)
C6 C5 C7 C8 -116.48(19)
N2 C7 C8 C13 -3.6(3)
C5 C7 C8 C13 95.4(2)
N2 C7 C8 C9 -179.5(2)
C5 C7 C8 C9 -80.5(3)
C13 C8 C9 C10 -1.2(3)
C7 C8 C9 C10 174.9(2)
C8 C9 C10 C11 0.2(4)
C9 C10 C11 C12 1.2(4)
C9 C10 C11 Cl1 -177.57(18)
C10 C11 C12 C13 -1.7(4)
Cl1 C11 C12 C13 177.16(17)
C11 C12 C13 C8 0.6(3)
C9 C8 C13 C12 0.8(3)
C7 C8 C13 C12 -175.1(2)
C6 N2 C14 C15 168.9(2)
C7 N2 C14 C15 -7.2(3)
C6 N2 C14 C19 -13.2(4)
C7 N2 C14 C19 170.8(2)
C19 C14 C15 C16 -0.2(3)
N2 C14 C15 C16 177.8(2)
C14 C15 C16 C17 0.9(3)
C20 O4 C17 C16 -5.7(4)
C20 O4 C17 C18 176.0(2)
C15 C16 C17 O4 -179.3(2)
C15 C16 C17 C18 -1.1(4)
O4 C17 C18 C19 179.0(2)
C16 C17 C18 C19 0.7(4)
C17 C18 C19 C14 0.0(4)
C15 C14 C19 C18 -0.2(3)
N2 C14 C19 C18 -178.2(2)
