#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/13/2221306.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_2221306
loop_
_publ_author_name
'Xu, Liang-zhong'
'Huang, Jin'
'Su, Qun-qun'
'Guo, Wei'
_publ_section_title
4-[(6-Chloro-2-pyridyl)methoxy]-3-(2,4-dichlorophenyl)-1-oxaspiro[4.5]dec-3-en-2-one
_journal_coeditor_code           BX2196
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o846
_journal_paper_doi               10.1107/S1600536809010101
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C21 H18 Cl3 N O3'
_chemical_formula_moiety         'C21 H18 Cl3 N O3'
_chemical_formula_sum            'C21 H18 Cl3 N O3'
_chemical_formula_weight         438.71
_chemical_name_systematic
;
4-[(6-Chloro-2-pyridyl)methoxy]-3-(2,4-dichlorophenyl)-1-oxaspiro[4.5]dec-\
3-en-2-one
;
_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'
_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                 95.77(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2457(14)
_cell_length_b                   13.108(3)
_cell_length_c                   21.054(4)
_cell_measurement_reflns_used    5265
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.948
_cell_measurement_theta_min      1.553
_cell_volume                     1989.5(7)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14740
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.83
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.483
_exptl_absorpt_correction_T_max  0.9716
_exptl_absorpt_correction_T_min  0.9180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.311
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3519
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0337
_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)+(0.053P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0892
_reflns_number_gt                3191
_reflns_number_total             3519
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bx2196.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2221306
_cod_database_fobs_code          2221306
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 -0.28480(7) -0.08999(4) 0.06950(2) 0.03906(15) Uani d . 1 . .
Cl Cl2 -0.06561(6) 0.21586(3) 0.228775(19) 0.02533(13) Uani d . 1 . .
Cl Cl3 0.36534(7) 0.22352(4) 0.06907(2) 0.03617(15) Uani d . 1 . .
O O1 0.00146(14) 0.14206(8) 0.42592(5) 0.0204(3) Uani d . 1 . .
O O2 -0.26135(15) 0.13568(9) 0.35960(5) 0.0248(3) Uani d . 1 . .
O O3 0.35068(14) 0.00872(8) 0.35405(5) 0.0226(3) Uani d . 1 . .
N N1 0.4102(2) 0.18419(11) 0.19104(7) 0.0264(3) Uani d . 1 . .
C C1 0.1925(2) 0.10733(12) 0.42562(7) 0.0188(3) Uani d . 1 . .
C C2 0.3193(2) 0.20111(12) 0.42615(8) 0.0239(4) Uani d . 1 . .
H H2A 0.4436 0.1795 0.4190 0.029 Uiso calc R 1 . .
H H2B 0.2745 0.2464 0.3915 0.029 Uiso calc R 1 . .
C C3 0.3264(2) 0.25889(13) 0.48925(8) 0.0275(4) Uani d . 1 . .
H H3A 0.2050 0.2870 0.4944 0.033 Uiso calc R 1 . .
H H3B 0.4135 0.3150 0.4889 0.033 Uiso calc R 1 . .
C C4 0.3862(3) 0.18769(13) 0.54514(8) 0.0292(4) Uani d . 1 . .
H H4A 0.5117 0.1641 0.5416 0.035 Uiso calc R 1 . .
H H4B 0.3862 0.2251 0.5849 0.035 Uiso calc R 1 . .
C C5 0.2574(2) 0.09592(13) 0.54645(8) 0.0259(4) Uani d . 1 . .
H H5A 0.1351 0.1188 0.5551 0.031 Uiso calc R 1 . .
H H5B 0.3042 0.0502 0.5806 0.031 Uiso calc R 1 . .
C C6 0.2430(2) 0.03854(12) 0.48280(7) 0.0211(4) Uani d . 1 . .
H H6A 0.3608 0.0058 0.4780 0.025 Uiso calc R 1 . .
H H6B 0.1498 -0.0145 0.4835 0.025 Uiso calc R 1 . .
C C7 0.1869(2) 0.05012(11) 0.36345(7) 0.0182(3) Uani d . 1 . .
C C8 0.3726(2) -0.04708(12) 0.29626(8) 0.0251(4) Uani d . 1 . .
H H8A 0.2760 -0.0984 0.2901 0.030 Uiso calc R 1 . .
H H8B 0.4911 -0.0822 0.3010 0.030 Uiso calc R 1 . .
C C9 0.3640(2) 0.01985(12) 0.23785(8) 0.0221(4) Uani d . 1 . .
C C10 0.3138(2) -0.02018(13) 0.17760(8) 0.0285(4) Uani d . 1 . .
H H10 0.2810 -0.0886 0.1730 0.034 Uiso calc R 1 . .
C C11 0.3125(2) 0.04149(14) 0.12452(8) 0.0293(4) Uani d . 1 . .
H H11 0.2799 0.0162 0.0837 0.035 Uiso calc R 1 . .
C C12 0.3619(2) 0.14262(13) 0.13470(8) 0.0254(4) Uani d . 1 . .
C C13 0.4111(2) 0.12222(13) 0.24178(8) 0.0247(4) Uani d . 1 . .
H H13 0.4453 0.1496 0.2820 0.030 Uiso calc R 1 . .
C C14 0.0183(2) 0.05485(11) 0.33042(7) 0.0185(3) Uani d . 1 . .
C C15 -0.0991(2) 0.11385(12) 0.37036(7) 0.0199(4) Uani d . 1 . .
C C16 -0.0574(2) 0.01791(12) 0.26666(7) 0.0190(3) Uani d . 1 . .
C C17 -0.0880(2) -0.08572(12) 0.25352(8) 0.0233(4) Uani d . 1 . .
H H17 -0.0618 -0.1332 0.2860 0.028 Uiso calc R 1 . .
C C18 -0.1565(2) -0.11919(13) 0.19334(8) 0.0263(4) Uani d . 1 . .
H H18 -0.1736 -0.1885 0.1853 0.032 Uiso calc R 1 . .
C C19 -0.1993(2) -0.04852(13) 0.14529(8) 0.0253(4) Uani d . 1 . .
C C20 -0.1746(2) 0.05474(12) 0.15634(8) 0.0229(4) Uani d . 1 . .
H H20 -0.2048 0.1020 0.1240 0.027 Uiso calc R 1 . .
C C21 -0.1040(2) 0.08598(11) 0.21652(8) 0.0185(3) Uani d . 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C15 O1 C1 . . 109.69(12) ?
C7 O3 C8 . . 120.36(13) ?
C12 N1 C13 . . 116.43(15) ?
O1 C1 C7 . . 102.52(12) ?
O1 C1 C6 . . 109.58(12) ?
C7 C1 C6 . . 112.12(13) ?
O1 C1 C2 . . 108.54(12) ?
C7 C1 C2 . . 111.66(12) ?
C6 C1 C2 . . 111.93(14) ?
C3 C2 C1 . . 111.83(13) ?
C3 C2 H2A . . 109.2 ?
C1 C2 H2A . . 109.2 ?
C3 C2 H2B . . 109.2 ?
C1 C2 H2B . . 109.2 ?
H2A C2 H2B . . 107.9 ?
C2 C3 C4 . . 110.44(14) ?
C2 C3 H3A . . 109.6 ?
C4 C3 H3A . . 109.6 ?
C2 C3 H3B . . 109.6 ?
C4 C3 H3B . . 109.6 ?
H3A C3 H3B . . 108.1 ?
C5 C4 C3 . . 111.65(14) ?
C5 C4 H4A . . 109.3 ?
C3 C4 H4A . . 109.3 ?
C5 C4 H4B . . 109.3 ?
C3 C4 H4B . . 109.3 ?
H4A C4 H4B . . 108.0 ?
C4 C5 C6 . . 111.10(14) ?
C4 C5 H5A . . 109.4 ?
C6 C5 H5A . . 109.4 ?
C4 C5 H5B . . 109.4 ?
C6 C5 H5B . . 109.4 ?
H5A C5 H5B . . 108.0 ?
C1 C6 C5 . . 113.06(13) ?
C1 C6 H6A . . 109.0 ?
C5 C6 H6A . . 109.0 ?
C1 C6 H6B . . 109.0 ?
C5 C6 H6B . . 109.0 ?
H6A C6 H6B . . 107.8 ?
O3 C7 C14 . . 135.67(15) ?
O3 C7 C1 . . 112.59(13) ?
C14 C7 C1 . . 111.73(13) ?
O3 C8 C9 . . 113.22(12) ?
O3 C8 H8A . . 108.9 ?
C9 C8 H8A . . 108.9 ?
O3 C8 H8B . . 108.9 ?
C9 C8 H8B . . 108.9 ?
H8A C8 H8B . . 107.7 ?
C13 C9 C10 . . 117.49(15) ?
C13 C9 C8 . . 121.71(15) ?
C10 C9 C8 . . 120.77(15) ?
C11 C10 C9 . . 119.95(16) ?
C11 C10 H10 . . 120.0 ?
C9 C10 H10 . . 120.0 ?
C10 C11 C12 . . 117.11(16) ?
C10 C11 H11 . . 121.4 ?
C12 C11 H11 . . 121.4 ?
N1 C12 C11 . . 125.13(16) ?
N1 C12 Cl3 . . 115.93(13) ?
C11 C12 Cl3 . . 118.94(13) ?
N1 C13 C9 . . 123.89(15) ?
N1 C13 H13 . . 118.1 ?
C9 C13 H13 . . 118.1 ?
C7 C14 C15 . . 105.99(14) ?
C7 C14 C16 . . 133.52(14) ?
C15 C14 C16 . . 120.44(14) ?
O2 C15 O1 . . 121.42(14) ?
O2 C15 C14 . . 128.58(15) ?
O1 C15 C14 . . 109.99(13) ?
C21 C16 C17 . . 116.66(15) ?
C21 C16 C14 . . 121.05(14) ?
C17 C16 C14 . . 122.28(14) ?
C18 C17 C16 . . 121.58(15) ?
C18 C17 H17 . . 119.2 ?
C16 C17 H17 . . 119.2 ?
C19 C18 C17 . . 119.35(15) ?
C19 C18 H18 . . 120.3 ?
C17 C18 H18 . . 120.3 ?
C20 C19 C18 . . 121.13(16) ?
C20 C19 Cl1 . . 119.24(13) ?
C18 C19 Cl1 . . 119.63(13) ?
C21 C20 C19 . . 118.36(15) ?
C21 C20 H20 . . 120.8 ?
C19 C20 H20 . . 120.8 ?
C20 C21 C16 . . 122.90(14) ?
C20 C21 Cl2 . . 117.74(12) ?
C16 C21 Cl2 . . 119.32(12) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C19 . 1.7398(17) ?
Cl2 C21 . 1.7400(16) ?
Cl3 C12 . 1.7440(17) ?
O1 C15 . 1.366(2) ?
O1 C1 . 1.4577(18) ?
O2 C15 . 1.2090(19) ?
O3 C7 . 1.3375(18) ?
O3 C8 . 1.4421(18) ?
N1 C12 . 1.320(2) ?
N1 C13 . 1.342(2) ?
C1 C7 . 1.505(2) ?
C1 C6 . 1.519(2) ?
C1 C2 . 1.534(2) ?
C2 C3 . 1.526(2) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.530(2) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.524(2) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.531(2) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C14 . 1.345(2) ?
C8 C9 . 1.507(2) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C13 . 1.385(2) ?
C9 C10 . 1.387(2) ?
C10 C11 . 1.378(2) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.384(2) ?
C11 H11 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 C15 . 1.474(2) ?
C14 C16 . 1.480(2) ?
C16 C21 . 1.398(2) ?
C16 C17 . 1.400(2) ?
C17 C18 . 1.385(2) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.384(2) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.382(2) ?
C20 C21 . 1.380(2) ?
C20 H20 . 0.9300 ?
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
C13 H13 O3 . 0.93 2.53 2.864(2) 102
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
C15 O1 C1 C7 . . . . -2.79(15) ?
C15 O1 C1 C6 . . . . -122.03(13) ?
C15 O1 C1 C2 . . . . 115.46(13) ?
O1 C1 C2 C3 . . . . 68.12(17) ?
C7 C1 C2 C3 . . . . -179.60(13) ?
C6 C1 C2 C3 . . . . -52.96(18) ?
C1 C2 C3 C4 . . . . 55.70(18) ?
C2 C3 C4 C5 . . . . -57.18(19) ?
C3 C4 C5 C6 . . . . 55.15(19) ?
O1 C1 C6 C5 . . . . -69.25(17) ?
C7 C1 C6 C5 . . . . 177.61(13) ?
C2 C1 C6 C5 . . . . 51.22(18) ?
C4 C5 C6 C1 . . . . -52.32(18) ?
C8 O3 C7 C14 . . . . 0.0(3) ?
C8 O3 C7 C1 . . . . -178.59(12) ?
O1 C1 C7 O3 . . . . -178.43(12) ?
C6 C1 C7 O3 . . . . -60.99(17) ?
C2 C1 C7 O3 . . . . 65.55(16) ?
O1 C1 C7 C14 . . . . 2.66(16) ?
C6 C1 C7 C14 . . . . 120.10(15) ?
C2 C1 C7 C14 . . . . -113.36(15) ?
C7 O3 C8 C9 . . . . 69.36(18) ?
O3 C8 C9 C13 . . . . 26.2(2) ?
O3 C8 C9 C10 . . . . -155.88(14) ?
C13 C9 C10 C11 . . . . 0.1(2) ?
C8 C9 C10 C11 . . . . -177.88(16) ?
C9 C10 C11 C12 . . . . -0.3(2) ?
C13 N1 C12 C11 . . . . 0.2(2) ?
C13 N1 C12 Cl3 . . . . -178.92(12) ?
C10 C11 C12 N1 . . . . 0.2(3) ?
C10 C11 C12 Cl3 . . . . 179.21(13) ?
C12 N1 C13 C9 . . . . -0.3(2) ?
C10 C9 C13 N1 . . . . 0.2(2) ?
C8 C9 C13 N1 . . . . 178.20(15) ?
O3 C7 C14 C15 . . . . 179.93(16) ?
C1 C7 C14 C15 . . . . -1.50(17) ?
O3 C7 C14 C16 . . . . -2.6(3) ?
C1 C7 C14 C16 . . . . 175.99(15) ?
C1 O1 C15 O2 . . . . -179.05(13) ?
C1 O1 C15 C14 . . . . 2.09(16) ?
C7 C14 C15 O2 . . . . -179.10(15) ?
C16 C14 C15 O2 . . . . 3.0(2) ?
C7 C14 C15 O1 . . . . -0.35(16) ?
C16 C14 C15 O1 . . . . -178.24(13) ?
C7 C14 C16 C21 . . . . -109.1(2) ?
C15 C14 C16 C21 . . . . 68.14(19) ?
C7 C14 C16 C17 . . . . 71.7(2) ?
C15 C14 C16 C17 . . . . -111.08(17) ?
C21 C16 C17 C18 . . . . 1.7(2) ?
C14 C16 C17 C18 . . . . -179.07(15) ?
C16 C17 C18 C19 . . . . -1.3(2) ?
C17 C18 C19 C20 . . . . 0.1(3) ?
C17 C18 C19 Cl1 . . . . 179.83(12) ?
C18 C19 C20 C21 . . . . 0.7(2) ?
Cl1 C19 C20 C21 . . . . -179.05(12) ?
C19 C20 C21 C16 . . . . -0.3(2) ?
C19 C20 C21 Cl2 . . . . 177.62(12) ?
C17 C16 C21 C20 . . . . -0.9(2) ?
C14 C16 C21 C20 . . . . 179.87(14) ?
C17 C16 C21 Cl2 . . . . -178.75(12) ?
C14 C16 C21 Cl2 . . . . 2.0(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742003
