#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/44/2224429.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_2224429
loop_
_publ_author_name
'Zhou, Yong'
'Cheng, Jing-Li'
'Zhu, Guo-Nian'
'Zhao, Jin-Hao'
_publ_section_title
;
 3-(2,4-Dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl
 4-chlorobenzoate
;
_journal_coeditor_code           SI2216
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2992
_journal_paper_doi               10.1107/S1600536809044109
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C22 H17 Cl3 O4'
_chemical_formula_moiety         'C22 H17 Cl3 O4'
_chemical_formula_sum            'C22 H17 Cl3 O4'
_chemical_formula_weight         451.73
_chemical_name_systematic
;
3-(2,4-Dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl 4-chlorobenzoate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 115.1875(12)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   14.7979(8)
_cell_length_b                   10.3483(5)
_cell_length_c                   15.0702(8)
_cell_measurement_reflns_used    13096
_cell_measurement_temperature    296.0(10)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.0
_cell_volume                     2088.33(19)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'CRYSTALS (Watkin et al.,  1996)'
_computing_publication_material  'CrystalStructure and PLATON (Spek, 2009)'
_computing_structure_refinement  'CRYSTALS (Watkin et al.,  1996)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      296.0(10)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19403
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.43
_exptl_absorpt_coefficient_mu    0.464
_exptl_absorpt_correction_T_max  0.878
_exptl_absorpt_correction_T_min  0.800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             928.00
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.54
_refine_diff_density_min         -0.43
_refine_ls_extinction_coef       13E1(2)
_refine_ls_extinction_method     'Larson (1970), equation 22'
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4756
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[0.0005Fo² + 3σ(Fo²)]/(4Fo²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1308
_reflns_number_gt                3289
_reflns_number_total             4756
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            si2216.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2224429
_cod_database_fobs_code          2224429
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,1/2+Z
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.59797(8) -0.25919(9) 0.12627(8) 0.0964(3) Uani d . 1.00 . .
Cl Cl2 0.43688(6) 0.27225(6) 0.35188(6) 0.0706(2) Uani d . 1.00 . .
Cl Cl3 0.74849(6) 0.44566(10) 0.67014(5) 0.0783(2) Uani d . 1.00 . .
O O1 0.41594(14) 0.74637(17) 0.27583(14) 0.0635(6) Uani d . 1.00 . .
O O2 0.32741(12) 0.64354(18) 0.13360(12) 0.0526(5) Uani d . 1.00 . .
O O3 0.43940(12) 0.33403(16) 0.14982(12) 0.0499(5) Uani d . 1.00 . .
O O4 0.60304(16) 0.3775(2) 0.2079(2) 0.0823(8) Uani d . 1.00 . .
C C1 0.32759(19) 0.5153(2) 0.09125(19) 0.0475(7) Uani d . 1.00 . .
C C2 0.41627(18) 0.4558(2) 0.17081(19) 0.0426(7) Uani d . 1.00 . .
C C3 0.45501(19) 0.5243(2) 0.25228(19) 0.0441(7) Uani d . 1.00 . .
C C4 0.4012(2) 0.6500(2) 0.2275(2) 0.0495(8) Uani d . 1.00 . .
C C5 0.3374(2) 0.5343(2) -0.00451(19) 0.0545(8) Uani d . 1.00 . .
C C6 0.2448(2) 0.5961(3) -0.0843(2) 0.0693(10) Uani d . 1.00 . .
C C7 0.1506(2) 0.5212(3) -0.0994(2) 0.0712(10) Uani d . 1.00 . .
C C8 0.1395(2) 0.5091(3) -0.0036(2) 0.0653(9) Uani d . 1.00 . .
C C9 0.23153(18) 0.4468(2) 0.0752(2) 0.0523(8) Uani d . 1.00 . .
C C10 0.5376(2) 0.3002(3) 0.1748(2) 0.0548(9) Uani d . 1.00 . .
C C11 0.54804(19) 0.1611(2) 0.15495(19) 0.0452(7) Uani d . 1.00 . .
C C12 0.6420(2) 0.1213(2) 0.1683(2) 0.0553(8) Uani d . 1.00 . .
C C13 0.6566(2) -0.0088(3) 0.1565(2) 0.0628(10) Uani d . 1.00 . .
C C14 0.5783(2) -0.0928(2) 0.1331(2) 0.0552(8) Uani d . 1.00 . .
C C15 0.4847(2) -0.0556(2) 0.1182(2) 0.0620(9) Uani d . 1.00 . .
C C16 0.4699(2) 0.0755(2) 0.1285(2) 0.0586(9) Uani d . 1.00 . .
C C17 0.53097(19) 0.5005(2) 0.35283(19) 0.0454(7) Uani d . 1.00 . .
C C18 0.52788(19) 0.3912(2) 0.4051(2) 0.0482(8) Uani d . 1.00 . .
C C19 0.5946(2) 0.3713(2) 0.5033(2) 0.0528(8) Uani d . 1.00 . .
C C20 0.6659(2) 0.4649(2) 0.5479(2) 0.0530(8) Uani d . 1.00 . .
C C21 0.6719(2) 0.5728(3) 0.4985(2) 0.0620(9) Uani d . 1.00 . .
C C22 0.6042(2) 0.5900(3) 0.4017(2) 0.0620(9) Uani d . 1.00 . .
H H12 0.6941 0.1801 0.1847 0.066 Uiso c R 1.00 . .
H H13 0.7188 -0.0386 0.1644 0.075 Uiso c R 1.00 . .
H H15 0.4330 -0.1150 0.1019 0.074 Uiso c R 1.00 . .
H H16 0.4067 0.1052 0.1174 0.070 Uiso c R 1.00 . .
H H19 0.5908 0.2979 0.5372 0.063 Uiso c R 1.00 . .
H H21 0.7210 0.6344 0.5297 0.074 Uiso c R 1.00 . .
H H22 0.6084 0.6641 0.3687 0.074 Uiso c R 1.00 . .
H H51 0.3944 0.5896 0.0079 0.065 Uiso c R 1.00 . .
H H52 0.3481 0.4507 -0.0276 0.065 Uiso c R 1.00 . .
H H61 0.2386 0.6841 -0.0654 0.083 Uiso c R 1.00 . .
H H62 0.2521 0.5969 -0.1454 0.083 Uiso c R 1.00 . .
H H71 0.1544 0.4355 -0.1236 0.085 Uiso c R 1.00 . .
H H72 0.0929 0.5662 -0.1472 0.085 Uiso c R 1.00 . .
H H81 0.0816 0.4562 -0.0146 0.078 Uiso c R 1.00 . .
H H82 0.1306 0.5944 0.0181 0.078 Uiso c R 1.00 . .
H H91 0.2245 0.4475 0.1363 0.063 Uiso c R 1.00 . .
H H92 0.2356 0.3583 0.0561 0.063 Uiso c R 1.00 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.148 0.159
;
International Tables for Crystallography
(1992, 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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O2 C4 . . . 110.07(18) ?
C2 O3 C10 . . . 120.29(19) ?
O2 C1 C2 . . . 100.83(17) ?
O2 C1 C5 . . . 108.2(2) ?
O2 C1 C9 . . . 108.5(2) ?
C2 C1 C5 . . . 114.3(2) ?
C2 C1 C9 . . . 112.5(2) ?
C5 C1 C9 . . . 111.7(2) ?
O3 C2 C1 . . . 114.5(2) ?
O3 C2 C3 . . . 130.8(2) ?
C1 C2 C3 . . . 114.5(2) ?
C2 C3 C4 . . . 105.2(2) ?
C2 C3 C17 . . . 135.0(2) ?
C4 C3 C17 . . . 119.8(2) ?
O1 C4 O2 . . . 121.7(2) ?
O1 C4 C3 . . . 129.5(2) ?
O2 C4 C3 . . . 108.8(2) ?
C1 C5 C6 . . . 112.7(2) ?
C5 C6 C7 . . . 111.2(2) ?
C6 C7 C8 . . . 111.2(2) ?
C7 C8 C9 . . . 110.7(2) ?
C1 C9 C8 . . . 113.3(2) ?
O3 C10 O4 . . . 121.2(2) ?
O3 C10 C11 . . . 112.1(2) ?
O4 C10 C11 . . . 126.7(2) ?
C10 C11 C12 . . . 116.3(2) ?
C10 C11 C16 . . . 122.3(2) ?
C12 C11 C16 . . . 121.4(2) ?
C11 C12 C13 . . . 118.2(2) ?
C12 C13 C14 . . . 119.3(3) ?
Cl1 C14 C13 . . . 119.7(2) ?
Cl1 C14 C15 . . . 116.7(2) ?
C13 C14 C15 . . . 123.6(2) ?
C14 C15 C16 . . . 117.0(2) ?
C11 C16 C15 . . . 120.5(2) ?
C3 C17 C18 . . . 121.6(2) ?
C3 C17 C22 . . . 121.3(2) ?
C18 C17 C22 . . . 116.9(2) ?
Cl2 C18 C17 . . . 121.20(17) ?
Cl2 C18 C19 . . . 116.1(2) ?
C17 C18 C19 . . . 122.6(2) ?
C18 C19 C20 . . . 117.4(2) ?
Cl3 C20 C19 . . . 119.0(2) ?
Cl3 C20 C21 . . . 119.5(2) ?
C19 C20 C21 . . . 121.6(2) ?
C20 C21 C22 . . . 119.5(2) ?
C17 C22 C21 . . . 121.9(2) ?
C1 C5 H51 . . . 108.7 ?
C1 C5 H52 . . . 108.7 ?
C6 C5 H51 . . . 108.7 ?
C6 C5 H52 . . . 108.7 ?
H51 C5 H52 . . . 109.5 ?
C5 C6 H61 . . . 109.0 ?
C5 C6 H62 . . . 109.0 ?
C7 C6 H61 . . . 109.0 ?
C7 C6 H62 . . . 109.0 ?
H61 C6 H62 . . . 109.5 ?
C6 C7 H71 . . . 109.1 ?
C6 C7 H72 . . . 109.1 ?
C8 C7 H71 . . . 109.1 ?
C8 C7 H72 . . . 109.1 ?
H71 C7 H72 . . . 109.5 ?
C7 C8 H81 . . . 109.2 ?
C7 C8 H82 . . . 109.2 ?
C9 C8 H81 . . . 109.2 ?
C9 C8 H82 . . . 109.2 ?
H81 C8 H82 . . . 109.5 ?
C1 C9 H91 . . . 108.5 ?
C1 C9 H92 . . . 108.5 ?
C8 C9 H91 . . . 108.5 ?
C8 C9 H92 . . . 108.5 ?
H91 C9 H92 . . . 109.5 ?
C11 C12 H12 . . . 120.9 ?
C13 C12 H12 . . . 120.9 ?
C12 C13 H13 . . . 120.4 ?
C14 C13 H13 . . . 120.4 ?
C14 C15 H15 . . . 121.5 ?
C16 C15 H15 . . . 121.5 ?
C11 C16 H16 . . . 119.8 ?
C15 C16 H16 . . . 119.8 ?
C18 C19 H19 . . . 121.3 ?
C20 C19 H19 . . . 121.3 ?
C20 C21 H21 . . . 120.2 ?
C22 C21 H21 . . . 120.2 ?
C17 C22 H22 . . . 119.1 ?
C21 C22 H22 . . . 119.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C14 . . 1.757(2) ?
Cl2 C18 . . 1.747(2) ?
Cl3 C20 . . 1.736(2) ?
O1 C4 . . 1.199(3) ?
O2 C1 . . 1.473(3) ?
O2 C4 . . 1.373(2) ?
O3 C2 . . 1.377(3) ?
O3 C10 . . 1.382(3) ?
O4 C10 . . 1.190(3) ?
C1 C2 . . 1.483(3) ?
C1 C5 . . 1.523(4) ?
C1 C9 . . 1.513(3) ?
C2 C3 . . 1.319(3) ?
C3 C4 . . 1.487(3) ?
C3 C17 . . 1.473(3) ?
C5 C6 . . 1.527(3) ?
C6 C7 . . 1.524(4) ?
C7 C8 . . 1.526(5) ?
C8 C9 . . 1.517(3) ?
C10 C11 . . 1.492(4) ?
C11 C12 . . 1.380(4) ?
C11 C16 . . 1.374(3) ?
C12 C13 . . 1.386(4) ?
C13 C14 . . 1.369(4) ?
C14 C15 . . 1.361(4) ?
C15 C16 . . 1.393(4) ?
C17 C18 . . 1.390(3) ?
C17 C22 . . 1.377(3) ?
C18 C19 . . 1.402(3) ?
C19 C20 . . 1.378(3) ?
C20 C21 . . 1.366(4) ?
C21 C22 . . 1.386(3) ?
C5 H51 . . 0.970 ?
C5 H52 . . 0.970 ?
C6 H61 . . 0.970 ?
C6 H62 . . 0.970 ?
C7 H71 . . 0.970 ?
C7 H72 . . 0.970 ?
C8 H81 . . 0.970 ?
C8 H82 . . 0.970 ?
C9 H91 . . 0.970 ?
C9 H92 . . 0.970 ?
C12 H12 . . 0.930 ?
C13 H13 . . 0.930 ?
C15 H15 . . 0.930 ?
C16 H16 . . 0.930 ?
C19 H19 . . 0.930 ?
C21 H21 . . 0.930 ?
C22 H22 . . 0.930 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C5 H52 Cl1 3_655 0.97 2.79 3.726(3) 162 yes
C16 H16 Cl3 4_454 0.93 2.82 3.595(3) 141 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 O2 C4 O1 . . . . 178.8(3) ?
C1 O2 C4 C3 . . . . 0.2(3) ?
C4 O2 C1 C2 . . . . -4.5(3) ?
C4 O2 C1 C5 . . . . -124.7(2) ?
C4 O2 C1 C9 . . . . 113.9(2) ?
C2 O3 C10 O4 . . . . -5.7(4) ?
C2 O3 C10 C11 . . . . 174.4(2) ?
C10 O3 C2 C1 . . . . 137.8(2) ?
C10 O3 C2 C3 . . . . -48.0(4) ?
O2 C1 C2 O3 . . . . -176.7(2) ?
O2 C1 C2 C3 . . . . 8.1(3) ?
O2 C1 C5 C6 . . . . -68.4(2) ?
O2 C1 C9 C8 . . . . 67.4(3) ?
C2 C1 C5 C6 . . . . -179.8(2) ?
C5 C1 C2 O3 . . . . -60.9(3) ?
C5 C1 C2 C3 . . . . 124.0(2) ?
C2 C1 C9 C8 . . . . 178.0(2) ?
C9 C1 C2 O3 . . . . 67.9(3) ?
C9 C1 C2 C3 . . . . -107.2(3) ?
C5 C1 C9 C8 . . . . -51.8(3) ?
C9 C1 C5 C6 . . . . 51.0(3) ?
O3 C2 C3 C4 . . . . 177.6(3) ?
O3 C2 C3 C17 . . . . -4.5(6) ?
C1 C2 C3 C4 . . . . -8.2(3) ?
C1 C2 C3 C17 . . . . 169.7(3) ?
C2 C3 C4 O1 . . . . -173.7(3) ?
C2 C3 C4 O2 . . . . 4.9(3) ?
C2 C3 C17 C18 . . . . -50.1(5) ?
C2 C3 C17 C22 . . . . 134.5(3) ?
C4 C3 C17 C18 . . . . 127.6(3) ?
C4 C3 C17 C22 . . . . -47.9(4) ?
C17 C3 C4 O1 . . . . 8.0(5) ?
C17 C3 C4 O2 . . . . -173.4(2) ?
C1 C5 C6 C7 . . . . -53.4(3) ?
C5 C6 C7 C8 . . . . 55.8(3) ?
C6 C7 C8 C9 . . . . -56.1(3) ?
C7 C8 C9 C1 . . . . 54.5(3) ?
O3 C10 C11 C12 . . . . 173.7(2) ?
O3 C10 C11 C16 . . . . -8.8(4) ?
O4 C10 C11 C12 . . . . -6.2(5) ?
O4 C10 C11 C16 . . . . 171.4(3) ?
C10 C11 C12 C13 . . . . 176.1(2) ?
C10 C11 C16 C15 . . . . -174.9(2) ?
C12 C11 C16 C15 . . . . 2.6(4) ?
C16 C11 C12 C13 . . . . -1.5(4) ?
C11 C12 C13 C14 . . . . -0.5(4) ?
C12 C13 C14 Cl1 . . . . -175.6(2) ?
C12 C13 C14 C15 . . . . 1.5(4) ?
Cl1 C14 C15 C16 . . . . 176.8(2) ?
C13 C14 C15 C16 . . . . -0.4(4) ?
C14 C15 C16 C11 . . . . -1.6(4) ?
C3 C17 C18 Cl2 . . . . 3.1(4) ?
C3 C17 C18 C19 . . . . -174.9(3) ?
C3 C17 C22 C21 . . . . 175.5(3) ?
C18 C17 C22 C21 . . . . -0.2(4) ?
C22 C17 C18 Cl2 . . . . 178.7(2) ?
C22 C17 C18 C19 . . . . 0.8(4) ?
Cl2 C18 C19 C20 . . . . -178.7(2) ?
C17 C18 C19 C20 . . . . -0.6(4) ?
C18 C19 C20 Cl3 . . . . 178.8(2) ?
C18 C19 C20 C21 . . . . -0.1(4) ?
Cl3 C20 C21 C22 . . . . -178.2(2) ?
C19 C20 C21 C22 . . . . 0.7(5) ?
C20 C21 C22 C17 . . . . -0.6(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743674
