#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/19/2201902.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_2201902
loop_
_publ_author_name
'Li, Xiao-Fang'
'Feng, Ya-Qing'
'Hu, Xiao-Fen'
'Xu, Mian'
_publ_section_title
;
 4-(4-Chlorophenyl)-1,3-diphenyl-7-oxa-1,2-diazaspiro[4.4]non-2-en-6-one
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o794
_journal_page_last               o796
_journal_paper_doi               10.1107/S1600536803009759
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C24 H19 Cl N2 O2'
_chemical_formula_moiety         'C24 H19 Cl N2 O2'
_chemical_formula_sum            'C24 H19 Cl N2 O2'
_chemical_formula_weight         402.86
_chemical_name_systematic
;
4-(4-Chlorophenyl)-1,3-diphenyl-7-oxa-1,2-diazaspiro[4.4]non-2-en-6-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 102.325(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.013(6)
_cell_length_b                   15.627(6)
_cell_length_c                   16.317(6)
_cell_measurement_reflns_used    907
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.77
_cell_measurement_theta_min      2.39
_cell_volume                     3989(3)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'SMART CCD area-detector'
_diffrn_measurement_method       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  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0592
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9301
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         1.84
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.414
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1225
_refine_ls_R_factor_gt           0.0543
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.084P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1310
_reflns_number_gt                2154
_reflns_number_total             4039
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6220.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2201902
_cod_database_fobs_code          2201902
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_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
_atom_site_type_symbol
Cl1 0.06404(5) 0.88675(8) 0.14477(6) 0.1081(4) Uani d . 1 . . Cl
N1 0.51756(12) 0.74185(13) 0.41532(13) 0.0510(5) Uani d . 1 . . N
N2 0.54456(12) 0.82442(14) 0.40529(13) 0.0510(5) Uani d . 1 . . N
O1 0.38566(12) 0.68136(12) 0.50917(12) 0.0654(6) Uani d . 1 . . O
O2 0.32198(11) 0.62775(13) 0.38593(13) 0.0696(6) Uani d . 1 . . O
C1 0.37840(15) 0.67854(17) 0.43477(19) 0.0484(6) Uani d . 1 . . C
C2 0.42539(14) 0.73343(15) 0.38178(14) 0.0419(6) Uani d . 1 . . C
C3 0.40205(16) 0.69071(18) 0.29555(16) 0.0567(7) Uani d . 1 . . C
H3A 0.3912 0.7332 0.2512 0.068 Uiso calc R 1 . . H
H3B 0.4475 0.6531 0.2867 0.068 Uiso calc R 1 . . H
C4 0.32204(18) 0.6404(2) 0.2977(2) 0.0755(9) Uani d . 1 . . C
H4A 0.2716 0.6720 0.2702 0.091 Uiso calc R 1 . . H
H4B 0.3227 0.5858 0.2696 0.091 Uiso calc R 1 . . H
C5 0.39684(14) 0.82861(15) 0.38827(15) 0.0432(6) Uani d . 1 . . C
H5 0.3858 0.8359 0.4447 0.052 Uiso calc R 1 . . H
C6 0.47944(15) 0.87515(16) 0.38733(15) 0.0451(6) Uani d . 1 . . C
C7 0.57841(15) 0.67546(16) 0.42321(15) 0.0452(6) Uani d . 1 . . C
C8 0.66421(15) 0.69477(18) 0.43080(16) 0.0534(7) Uani d . 1 . . C
H8 0.6814 0.7513 0.4280 0.064 Uiso calc R 1 . . H
C9 0.72415(17) 0.6297(2) 0.44256(18) 0.0645(8) Uani d . 1 . . C
H9 0.7817 0.6432 0.4487 0.077 Uiso calc R 1 . . H
C10 0.70030(18) 0.5459(2) 0.44531(18) 0.0687(8) Uani d . 1 . . C
H10 0.7411 0.5026 0.4528 0.082 Uiso calc R 1 . . H
C11 0.61563(19) 0.52664(19) 0.43685(19) 0.0672(8) Uani d . 1 . . C
H11 0.5988 0.4698 0.4382 0.081 Uiso calc R 1 . . H
C12 0.55474(16) 0.59065(17) 0.42631(17) 0.0578(7) Uani d . 1 . . C
H12 0.4974 0.5766 0.4213 0.069 Uiso calc R 1 . . H
C13 0.31455(14) 0.84996(15) 0.32727(15) 0.0424(6) Uani d . 1 . . C
C14 0.31225(16) 0.87577(17) 0.24559(16) 0.0574(7) Uani d . 1 . . C
H14 0.3632 0.8850 0.2282 0.069 Uiso calc R 1 . . H
C15 0.23534(17) 0.88798(19) 0.18957(17) 0.0644(8) Uani d . 1 . . C
H15 0.2345 0.9054 0.1349 0.077 Uiso calc R 1 . . H
C16 0.16018(16) 0.87412(18) 0.21525(18) 0.0586(7) Uani d . 1 . . C
C17 0.16097(16) 0.84983(17) 0.29655(18) 0.0564(7) Uani d . 1 . . C
H17 0.1099 0.8414 0.3138 0.068 Uiso calc R 1 . . H
C18 0.23817(15) 0.83808(16) 0.35223(16) 0.0473(6) Uani d . 1 . . C
H18 0.2387 0.8220 0.4072 0.057 Uiso calc R 1 . . H
C19 0.49231(15) 0.96739(16) 0.38210(15) 0.0459(6) Uani d . 1 . . C
C20 0.42589(18) 1.02534(19) 0.37186(19) 0.0683(8) Uani d . 1 . . C
H20 0.3703 1.0058 0.3677 0.082 Uiso calc R 1 . . H
C21 0.4411(2) 1.11219(19) 0.3677(2) 0.0799(9) Uani d . 1 . . C
H21 0.3956 1.1505 0.3600 0.096 Uiso calc R 1 . . H
C22 0.5224(2) 1.1421(2) 0.37477(19) 0.0756(9) Uani d . 1 . . C
H22 0.5324 1.2005 0.3717 0.091 Uiso calc R 1 . . H
C23 0.5888(2) 1.0856(2) 0.38635(19) 0.0732(9) Uani d . 1 . . C
H23 0.6443 1.1058 0.3914 0.088 Uiso calc R 1 . . H
C24 0.57464(17) 0.99941(18) 0.39062(16) 0.0578(7) Uani d . 1 . . C
H24 0.6207 0.9618 0.3993 0.069 Uiso calc R 1 . . H
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_publ_flag
N2 N1 C7 118.04(19) y
N2 N1 C2 110.80(18) y
C7 N1 C2 126.1(2) y
C6 N2 N1 109.99(19) y
C1 O2 C4 111.6(2) ?
O1 C1 O2 122.4(2) ?
O1 C1 C2 127.0(3) ?
O2 C1 C2 110.5(2) ?
N1 C2 C1 114.70(19) ?
N1 C2 C3 114.29(19) ?
C1 C2 C3 102.9(2) ?
N1 C2 C5 100.06(18) ?
C1 C2 C5 108.01(18) ?
C3 C2 C5 117.3(2) ?
C4 C3 C2 104.3(2) ?
C4 C3 H3A 110.9 ?
C2 C3 H3A 110.9 ?
C4 C3 H3B 110.9 ?
C2 C3 H3B 110.9 ?
H3A C3 H3B 108.9 ?
O2 C4 C3 105.9(2) ?
O2 C4 H4A 110.6 ?
C3 C4 H4A 110.6 ?
O2 C4 H4B 110.6 ?
C3 C4 H4B 110.6 ?
H4A C4 H4B 108.7 ?
C13 C5 C6 122.0(2) ?
C13 C5 C2 113.06(19) ?
C6 C5 C2 100.80(17) ?
C13 C5 H5 106.7 ?
C6 C5 H5 106.7 ?
C2 C5 H5 106.7 ?
N2 C6 C19 120.1(2) ?
N2 C6 C5 111.6(2) ?
C19 C6 C5 127.6(2) ?
C12 C7 C8 118.7(2) ?
C12 C7 N1 121.3(2) ?
C8 C7 N1 120.0(2) ?
C9 C8 C7 119.8(3) ?
C9 C8 H8 120.1 ?
C7 C8 H8 120.1 ?
C10 C9 C8 121.2(3) ?
C10 C9 H9 119.4 ?
C8 C9 H9 119.4 ?
C11 C10 C9 119.0(3) ?
C11 C10 H10 120.5 ?
C9 C10 H10 120.5 ?
C10 C11 C12 120.8(3) ?
C10 C11 H11 119.6 ?
C12 C11 H11 119.6 ?
C11 C12 C7 120.5(2) ?
C11 C12 H12 119.8 ?
C7 C12 H12 119.8 ?
C18 C13 C14 118.6(2) ?
C18 C13 C5 118.6(2) ?
C14 C13 C5 122.6(2) ?
C15 C14 C13 120.9(2) ?
C15 C14 H14 119.5 ?
C13 C14 H14 119.5 ?
C16 C15 C14 119.5(2) ?
C16 C15 H15 120.3 ?
C14 C15 H15 120.3 ?
C15 C16 C17 120.6(2) ?
C15 C16 Cl1 119.6(2) ?
C17 C16 Cl1 119.8(2) ?
C16 C17 C18 119.5(2) ?
C16 C17 H17 120.2 ?
C18 C17 H17 120.2 ?
C17 C18 C13 120.8(2) ?
C17 C18 H18 119.6 ?
C13 C18 H18 119.6 ?
C20 C19 C24 117.8(2) ?
C20 C19 C6 122.7(2) ?
C24 C19 C6 119.5(2) ?
C19 C20 C21 120.7(3) ?
C19 C20 H20 119.6 ?
C21 C20 H20 119.6 ?
C22 C21 C20 120.5(3) ?
C22 C21 H21 119.8 ?
C20 C21 H21 119.8 ?
C23 C22 C21 119.4(3) ?
C23 C22 H22 120.3 ?
C21 C22 H22 120.3 ?
C22 C23 C24 120.7(3) ?
C22 C23 H23 119.7 ?
C24 C23 H23 119.7 ?
C23 C24 C19 120.9(3) ?
C23 C24 H24 119.6 ?
C19 C24 H24 119.6 ?
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 C16 . 1.725(3) ?
N1 N2 . 1.382(3) y
N1 C7 . 1.410(3) y
N1 C2 . 1.466(3) y
N2 C6 . 1.293(3) y
O1 C1 . 1.196(3) y
O2 C1 . 1.332(3) y
O2 C4 . 1.453(3) y
C1 C2 . 1.526(3) y
C2 C3 . 1.530(3) y
C2 C5 . 1.566(3) y
C3 C4 . 1.510(4) y
C3 H3A . 0.97 ?
C3 H3B . 0.97 ?
C4 H4A . 0.97 ?
C4 H4B . 0.97 ?
C5 C13 . 1.509(3) ?
C5 C6 . 1.512(3) ?
C5 H5 . 0.98 ?
C6 C19 . 1.461(3) ?
C7 C12 . 1.382(4) ?
C7 C8 . 1.386(3) ?
C8 C9 . 1.383(4) ?
C8 H8 . 0.93 ?
C9 C10 . 1.368(4) ?
C9 H9 . 0.93 ?
C10 C11 . 1.367(4) ?
C10 H10 . 0.93 ?
C11 C12 . 1.382(4) ?
C11 H11 . 0.93 ?
C12 H12 . 0.93 ?
C13 C18 . 1.382(3) ?
C13 C14 . 1.385(3) ?
C14 C15 . 1.381(3) ?
C14 H14 . 0.93 ?
C15 C16 . 1.373(4) ?
C15 H15 . 0.93 ?
C16 C17 . 1.377(4) ?
C17 C18 . 1.381(3) ?
C17 H17 . 0.93 ?
C18 H18 . 0.93 ?
C19 C20 . 1.380(4) ?
C19 C24 . 1.389(3) ?
C20 C21 . 1.383(4) ?
C20 H20 . 0.93 ?
C21 C22 . 1.364(4) ?
C21 H21 . 0.93 ?
C22 C23 . 1.364(4) ?
C22 H22 . 0.93 ?
C23 C24 . 1.371(4) ?
C23 H23 . 0.93 ?
C24 H24 . 0.93 ?
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
C8 H8 N2 1_555 0.93 2.43 2.758(4) 101 yes
C11 H11 O1 5_666 0.93 2.51 3.369(4) 154 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
_geom_torsion_publ_flag
C7 N1 N2 C6 171.0(2) ?
C2 N1 N2 C6 14.7(3) ?
C4 O2 C1 O1 176.2(3) ?
C4 O2 C1 C2 -0.4(3) ?
N2 N1 C2 C1 -139.8(2) ?
C7 N1 C2 C1 66.2(3) ?
N2 N1 C2 C3 101.8(2) ?
C7 N1 C2 C3 -52.3(3) ?
N2 N1 C2 C5 -24.5(2) ?
C7 N1 C2 C5 -178.5(2) ?
O1 C1 C2 N1 45.8(4) ?
O2 C1 C2 N1 -137.8(2) ?
O1 C1 C2 C3 170.5(3) ?
O2 C1 C2 C3 -13.1(3) ?
O1 C1 C2 C5 -64.8(3) ?
O2 C1 C2 C5 111.6(2) ?
N1 C2 C3 C4 145.5(2) ?
C1 C2 C3 C4 20.5(3) ?
C5 C2 C3 C4 -97.8(2) ?
C1 O2 C4 C3 14.1(3) ?
C2 C3 C4 O2 -21.4(3) ?
N1 C2 C5 C13 155.64(18) ?
C1 C2 C5 C13 -84.1(2) ?
C3 C2 C5 C13 31.5(3) ?
N1 C2 C5 C6 23.8(2) ?
C1 C2 C5 C6 144.1(2) ?
C3 C2 C5 C6 -100.4(2) ?
N1 N2 C6 C19 173.8(2) ?
N1 N2 C6 C5 3.3(3) ?
C13 C5 C6 N2 -144.1(2) ?
C2 C5 C6 N2 -18.0(3) ?
C13 C5 C6 C19 46.3(4) ?
C2 C5 C6 C19 172.4(2) ?
N2 N1 C7 C12 -174.5(2) y
C2 N1 C7 C12 -22.1(4) ?
N2 N1 C7 C8 7.7(3) ?
C2 N1 C7 C8 160.0(2) ?
C12 C7 C8 C9 -1.0(4) ?
N1 C7 C8 C9 176.9(2) ?
C7 C8 C9 C10 1.2(4) ?
C8 C9 C10 C11 -0.5(5) ?
C9 C10 C11 C12 -0.5(5) ?
C10 C11 C12 C7 0.7(4) ?
C8 C7 C12 C11 0.1(4) ?
N1 C7 C12 C11 -177.8(2) ?
C6 C5 C13 C18 -150.0(2) ?
C2 C5 C13 C18 89.6(3) ?
C6 C5 C13 C14 34.2(4) ?
C2 C5 C13 C14 -86.2(3) ?
C18 C13 C14 C15 -1.2(4) ?
C5 C13 C14 C15 174.6(3) ?
C13 C14 C15 C16 -0.1(4) ?
C14 C15 C16 C17 1.2(4) ?
C14 C15 C16 Cl1 -178.4(2) ?
C15 C16 C17 C18 -1.0(4) ?
Cl1 C16 C17 C18 178.7(2) ?
C16 C17 C18 C13 -0.3(4) ?
C14 C13 C18 C17 1.4(4) ?
C5 C13 C18 C17 -174.6(2) ?
N2 C6 C19 C20 -173.1(3) y
C5 C6 C19 C20 -4.2(4) ?
N2 C6 C19 C24 4.6(4) ?
C5 C6 C19 C24 173.5(2) ?
C24 C19 C20 C21 2.0(4) ?
C6 C19 C20 C21 179.7(3) ?
C19 C20 C21 C22 -0.9(5) ?
C20 C21 C22 C23 -0.2(5) ?
C21 C22 C23 C24 0.2(5) ?
C22 C23 C24 C19 0.9(4) ?
C20 C19 C24 C23 -2.0(4) ?
C6 C19 C24 C23 -179.7(2) ?
