#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/03/2200306.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_2200306
loop_
_publ_author_name
'Bruno, Giuseppe'
'Nicoló, Francesco'
'Rotondo, Archimede'
'Foti, Francesco'
'Risitano, Francesco'
'Grassi, Giovanni'
'Bilardo, Cristina'
_publ_section_title
9-(2-Methoxybenzylidene)-6-(2-methoxyphenyl)-4,8-diphenyl-2-oxa-3,7-diazaspiro[4.4]nona-3,7-dien-1-one
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o399
_journal_page_last               o401
_journal_paper_doi               10.1107/S160053680100561X
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C33 H26 N2 O4'
_chemical_formula_moiety         'C33 H26 N2 O4'
_chemical_formula_sum            'C33 H26 N2 O4'
_chemical_formula_weight         514.56
_chemical_name_systematic
;
9-(2-Methoxy-benzylidene)-6-(2-methoxy-phenyl)-4,8-diphenyl-2-oxa-
3,7-diazaspiro[4.4]nona-3,7-dien-1-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                99.172(19)
_cell_angle_beta                 101.131(17)
_cell_angle_gamma                101.239(18)
_cell_formula_units_Z            2
_cell_length_a                   9.127(2)
_cell_length_b                   10.450(3)
_cell_length_c                   14.632(3)
_cell_measurement_reflns_used    33
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.93
_cell_measurement_theta_min      5.98
_cell_volume                     1314.6(6)
_computing_cell_refinement       P3/V
_computing_data_collection       'P3/V (Siemens,1989)'
_computing_data_reduction        'SHELXTL-Plus (Sheldrick, 1990)'
_computing_molecular_graphics    'XPW (Siemens, 1996)'
_computing_publication_material  'PARST97 (Nardelli, 1995) and SHELXL97'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .000
_diffrn_measured_fraction_theta_max .999
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0315
_diffrn_reflns_av_sigmaI/netI    .0990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6449
_diffrn_reflns_theta_full        .50
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 197
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             540
_exptl_crystal_size_max          .17
_exptl_crystal_size_mid          .13
_exptl_crystal_size_min          .10
_refine_diff_density_max         .136
_refine_diff_density_min         -.123
_refine_ls_extinction_coef       .0066(10)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   .716
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         6067
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .716
_refine_ls_R_factor_all          .1264
_refine_ls_R_factor_gt           .0414
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0434P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .0972
_reflns_number_gt                2324
_reflns_number_total             6067
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            na6058.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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_cell_volume        1314.6(5)
_cod_database_code               2200306
_cod_database_fobs_code          2200306
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O1 -.10977(17) .19704(15) .05703(10) .0697(4) Uani d . 1 . . O
O2 .06428(19) .08620(16) .10916(11) .0778(5) Uani d . 1 . . O
O3 -.44275(16) .06542(16) .18440(11) .0767(5) Uani d . 1 . . O
O4 .13162(16) .62202(13) .38007(11) .0627(4) Uani d . 1 . . O
N1 -.1893(2) .28770(18) .09999(12) .0623(5) Uani d . 1 . . N
N2 -.01940(19) .05973(15) .33299(11) .0522(5) Uani d . 1 . . N
C1 -.0554(2) .20630(18) .22057(13) .0427(5) Uani d . 1 . . C
C2 -.1566(2) .29628(19) .19064(14) .0472(5) Uani d . 1 . . C
C3 -.0222(2) .1529(2) .12636(15) .0546(6) Uani d . 1 . . C
C4 -.1401(2) .08823(18) .26221(13) .0465(5) Uani d . 1 . . C
H4A -.2103 .1237 .2968 .056 Uiso calc R 1 . . H
C5 .1027(2) .15468(18) .35306(13) .0438(5) Uani d . 1 . . C
C6 .0927(2) .26075(18) .29690(13) .0416(5) Uani d . 1 . . C
C7 -.2340(2) -.03312(19) .18993(14) .0502(5) Uani d . 1 . . C
C8 -.1717(3) -.1378(2) .16066(17) .0764(7) Uani d . 1 . . C
H8A -.0686 -.1329 .1857 .092 Uiso calc R 1 . . H
C9 -.2581(4) -.2496(3) .0953(2) .1033(10) Uani d . 1 . . C
H9A -.2135 -.3189 .0758 .124 Uiso calc R 1 . . H
C10 -.4097(4) -.2574(3) .0596(2) .1042(10) Uani d . 1 . . C
H10A -.4689 -.3329 .0157 .125 Uiso calc R 1 . . H
C11 -.4760(3) -.1553(3) .08741(18) .0842(8) Uani d . 1 . . C
H11A -.5796 -.1618 .0626 .101 Uiso calc R 1 . . H
C12 -.3888(3) -.0427(2) .15233(16) .0594(6) Uani d . 1 . . C
C13 -.5991(3) .0641(3) .1489(2) .1016(9) Uani d . 1 . . C
H13A -.6206 .1455 .1775 .122 Uiso calc R 1 . . H
H13B -.6633 -.0101 .1640 .122 Uiso calc R 1 . . H
H13C -.6192 .0558 .0811 .122 Uiso calc R 1 . . H
C14 -.2262(2) .38041(18) .25122(15) .0484(5) Uani d . 1 . . C
C15 -.3275(3) .4497(2) .21214(18) .0766(7) Uani d . 1 . . C
H15A -.3502 .4449 .1467 .092 Uiso calc R 1 . . H
C16 -.3958(3) .5264(3) .2692(3) .0960(10) Uani d . 1 . . C
H16A -.4638 .5729 .2418 .115 Uiso calc R 1 . . H
C17 -.3644(3) .5347(2) .3659(2) .0851(8) Uani d . 1 . . C
H17A -.4125 .5847 .4038 .102 Uiso calc R 1 . . H
C18 -.2614(3) .4686(2) .40581(19) .0758(7) Uani d . 1 . . C
H18A -.2376 .4749 .4713 .091 Uiso calc R 1 . . H
C19 -.1932(3) .3928(2) .34877(16) .0621(6) Uani d . 1 . . C
H19A -.1229 .3488 .3767 .075 Uiso calc R 1 . . H
C20 .2378(2) .15512(17) .42693(13) .0435(5) Uani d . 1 . . C
C21 .3866(2) .19547(19) .41597(15) .0546(6) Uani d . 1 . . C
H21A .4024 .2241 .3609 .066 Uiso calc R 1 . . H
C22 .5108(2) .1935(2) .48570(17) .0656(7) Uani d . 1 . . C
H22A .6098 .2197 .4771 .079 Uiso calc R 1 . . H
C23 .4892(3) .1531(2) .56798(17) .0685(7) Uani d . 1 . . C
H23A .5732 .1537 .6157 .082 Uiso calc R 1 . . H
C24 .3423(3) .1118(2) .57934(15) .0615(6) Uani d . 1 . . C
H24A .3271 .0829 .6344 .074 Uiso calc R 1 . . H
C25 .2183(2) .11304(17) .50995(14) .0509(5) Uani d . 1 . . C
H25A .1197 .0852 .5186 .061 Uiso calc R 1 . . H
C26 .1870(2) .38002(18) .31301(13) .0476(5) Uani d . 1 . . C
H26A .2679 .4026 .3666 .057 Uiso calc R 1 . . H
C27 .1740(2) .48004(19) .25258(15) .0488(5) Uani d . 1 . . C
C28 .1902(2) .4540(2) .15946(16) .0660(6) Uani d . 1 . . C
H28A .2097 .3729 .1348 .079 Uiso calc R 1 . . H
C29 .1778(3) .5481(3) .10244(18) .0778(7) Uani d . 1 . . C
H29A .1879 .5301 .0399 .093 Uiso calc R 1 . . H
C30 .1504(3) .6678(3) .1399(2) .0799(8) Uani d . 1 . . C
H30A .1410 .7306 .1020 .096 Uiso calc R 1 . . H
C31 .1365(2) .6964(2) .23166(18) .0678(7) Uani d . 1 . . C
H31A .1197 .7787 .2562 .081 Uiso calc R 1 . . H
C32 .1475(2) .6025(2) .28819(16) .0534(6) Uani d . 1 . . C
C33 .0652(3) .7288(2) .41123(17) .0815(8) Uani d . 1 . . C
H33A .0604 .7320 .4765 .122 Uiso calc R 1 . . H
H33C -.0366 .7150 .3726 .122 Uiso calc R 1 . . H
H33D .1270 .8115 .4056 .122 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 .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-2 -2 5
-2 -1 4
-3 -1 0
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
C3 O1 N1 109.45(16) ?
C12 O3 C13 118.61(19) yes
C32 O4 C33 117.50(16) yes
C2 N1 O1 108.89(16) ?
C5 N2 C4 110.15(14) ?
C2 C1 C3 100.42(15) yes
C2 C1 C6 120.68(16) yes
C3 C1 C6 110.80(16) yes
C2 C1 C4 112.84(15) yes
C3 C1 C4 110.79(16) yes
C6 C1 C4 101.51(13) ?
N1 C2 C14 119.84(17) ?
N1 C2 C1 112.62(19) ?
C14 C2 C1 127.38(17) ?
O2 C3 O1 121.9(2) yes
O2 C3 C1 129.93(19) yes
O1 C3 C1 108.16(18) ?
N2 C4 C7 113.56(15) ?
N2 C4 C1 105.44(14) ?
C7 C4 C1 115.81(16) ?
N2 C5 C20 121.16(16) ?
N2 C5 C6 114.44(16) ?
C20 C5 C6 124.40(18) ?
C26 C6 C5 127.72(17) ?
C26 C6 C1 127.28(16) ?
C5 C6 C1 104.89(16) ?
C8 C7 C12 118.3(2) ?
C8 C7 C4 121.70(19) ?
C12 C7 C4 119.97(19) ?
C7 C8 C9 121.7(2) ?
C10 C9 C8 119.1(3) ?
C9 C10 C11 120.8(3) ?
C10 C11 C12 119.9(3) ?
O3 C12 C11 124.8(2) yes
O3 C12 C7 115.1(2) yes
C11 C12 C7 120.1(2) ?
C15 C14 C19 117.7(2) ?
C15 C14 C2 120.7(2) ?
C19 C14 C2 121.53(17) ?
C14 C15 C16 120.6(2) ?
C17 C16 C15 120.7(2) ?
C18 C17 C16 119.3(3) ?
C17 C18 C19 119.8(2) ?
C18 C19 C14 121.8(2) ?
C25 C20 C21 118.10(18) ?
C25 C20 C5 119.96(18) ?
C21 C20 C5 121.94(18) ?
C22 C21 C20 120.8(2) ?
C23 C22 C21 120.2(2) ?
C22 C23 C24 119.5(2) ?
C25 C24 C23 120.4(2) ?
C24 C25 C20 120.9(2) ?
C6 C26 C27 125.27(18) yes
C32 C27 C28 118.59(18) ?
C32 C27 C26 120.73(19) ?
C28 C27 C26 120.67(19) ?
C27 C28 C29 120.7(2) ?
C30 C29 C28 119.0(2) ?
C31 C30 C29 121.3(2) ?
C30 C31 C32 119.8(2) ?
O4 C32 C31 123.5(2) yes
O4 C32 C27 115.87(17) yes
C31 C32 C27 120.6(2) ?
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
O1 C3 . 1.364(2) yes
O1 N1 . 1.440(2) yes
O2 C3 . 1.187(2) yes
O3 C12 . 1.369(3) yes
O3 C13 . 1.417(2) yes
O4 C32 . 1.367(2) yes
O4 C33 . 1.425(2) yes
N1 C2 . 1.287(2) yes
N2 C5 . 1.289(2) yes
N2 C4 . 1.470(2) yes
C1 C2 . 1.498(2) yes
C1 C3 . 1.512(3) yes
C1 C6 . 1.520(2) yes
C1 C4 . 1.594(2) yes
C2 C14 . 1.466(3) ?
C4 C7 . 1.503(3) yes
C5 C20 . 1.473(2) yes
C5 C6 . 1.488(2) yes
C6 C26 . 1.327(2) yes
C7 C8 . 1.374(3) ?
C7 C12 . 1.392(3) ?
C8 C9 . 1.376(3) ?
C9 C10 . 1.364(4) ?
C10 C11 . 1.371(4) ?
C11 C12 . 1.381(3) ?
C14 C15 . 1.377(3) ?
C14 C19 . 1.380(3) ?
C15 C16 . 1.382(3) ?
C16 C17 . 1.373(4) ?
C17 C18 . 1.368(3) ?
C18 C19 . 1.376(3) ?
C20 C25 . 1.387(2) ?
C20 C21 . 1.389(3) ?
C21 C22 . 1.377(3) ?
C22 C23 . 1.374(3) ?
C23 C24 . 1.376(3) ?
C24 C25 . 1.370(3) ?
C26 C27 . 1.480(2) yes
C27 C32 . 1.388(3) ?
C27 C28 . 1.389(3) ?
C28 C29 . 1.395(3) ?
C29 C30 . 1.372(3) ?
C30 C31 . 1.363(3) ?
C31 C32 . 1.386(3) ?
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
C4 H4A O3 . .98 2.32 2.725(2) 103 yes
C8 H8A O2 . .93 2.87 3.148(3) 98 ?
C8 H8A N2 . .93 2.61 2.902(3) 99 ?
C15 H15A N1 . .93 2.51 2.810(3) 99 yes
C25 H25A N2 . .93 2.71 2.936(3) 94 ?
C13 H13A O2 1_455 .96 2.77 3.076(3) 100 ?
C30 H30A O1 2_565 .93 2.54 3.396(3) 153 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
C3 O1 N1 C2 -1.8(2) ?
O1 N1 C2 C14 -178.58(16) ?
O1 N1 C2 C1 -2.8(2) ?
C3 C1 C2 N1 5.7(2) ?
C6 C1 C2 N1 127.63(19) ?
C4 C1 C2 N1 -112.26(19) ?
C3 C1 C2 C14 -178.88(18) ?
C6 C1 C2 C14 -57.0(3) ?
C4 C1 C2 C14 63.1(2) ?
N1 O1 C3 O2 -173.32(19) ?
N1 O1 C3 C1 5.5(2) ?
C2 C1 C3 O2 172.1(2) ?
C6 C1 C3 O2 43.5(3) ?
C4 C1 C3 O2 -68.4(3) ?
C2 C1 C3 O1 -6.5(2) ?
C6 C1 C3 O1 -135.18(16) ?
C4 C1 C3 O1 112.95(17) ?
C5 N2 C4 C7 141.90(18) ?
C5 N2 C4 C1 14.1(2) ?
C2 C1 C4 N2 -149.07(16) ?
C3 C1 C4 N2 99.23(17) ?
C6 C1 C4 N2 -18.48(18) ?
C2 C1 C4 C7 84.5(2) ?
C3 C1 C4 C7 -27.2(2) ?
C6 C1 C4 C7 -144.93(16) ?
C4 N2 C5 C20 175.92(17) ?
C4 N2 C5 C6 -3.3(2) ?
N2 C5 C6 C26 167.00(19) ?
C20 C5 C6 C26 -12.2(3) ?
N2 C5 C6 C1 -9.4(2) ?
C20 C5 C6 C1 171.37(17) ?
C2 C1 C6 C26 -34.5(3) ?
C3 C1 C6 C26 82.2(2) ?
C4 C1 C6 C26 -160.08(19) ?
C2 C1 C6 C5 141.88(17) ?
C3 C1 C6 C5 -101.35(17) ?
C4 C1 C6 C5 16.34(18) ?
N2 C4 C7 C8 -31.9(3) yes
C1 C4 C7 C8 90.4(2) ?
N2 C4 C7 C12 146.80(18) ?
C1 C4 C7 C12 -91.0(2) ?
C12 C7 C8 C9 .5(4) ?
C4 C7 C8 C9 179.2(2) ?
C7 C8 C9 C10 -.8(4) ?
C8 C9 C10 C11 .4(5) ?
C9 C10 C11 C12 .1(4) ?
C13 O3 C12 C11 -.4(3) ?
C13 O3 C12 C7 179.44(19) yes
C10 C11 C12 O3 179.4(2) ?
C10 C11 C12 C7 -.4(4) ?
C8 C7 C12 O3 -179.8(2) ?
C4 C7 C12 O3 1.5(3) ?
C8 C7 C12 C11 .1(3) ?
C4 C7 C12 C11 -178.6(2) ?
N1 C2 C14 C15 .6(3) yes
C1 C2 C14 C15 -174.53(19) ?
N1 C2 C14 C19 -179.57(19) ?
C1 C2 C14 C19 5.3(3) ?
C19 C14 C15 C16 -1.4(3) ?
C2 C14 C15 C16 178.4(2) ?
C14 C15 C16 C17 -.2(4) ?
C15 C16 C17 C18 1.6(4) ?
C16 C17 C18 C19 -1.3(4) ?
C17 C18 C19 C14 -.4(3) ?
C15 C14 C19 C18 1.7(3) ?
C2 C14 C19 C18 -178.12(19) ?
N2 C5 C20 C25 -38.8(3) ?
C6 C5 C20 C25 140.34(19) ?
N2 C5 C20 C21 140.5(2) ?
C6 C5 C20 C21 -40.4(3) yes
C25 C20 C21 C22 .0(3) ?
C5 C20 C21 C22 -179.28(18) ?
C20 C21 C22 C23 -.9(3) ?
C21 C22 C23 C24 1.4(3) ?
C22 C23 C24 C25 -1.1(3) ?
C23 C24 C25 C20 .3(3) ?
C21 C20 C25 C24 .3(3) ?
C5 C20 C25 C24 179.59(18) ?
C5 C6 C26 C27 177.86(19) ?
C1 C6 C26 C27 -6.5(3) ?
C6 C26 C27 C32 116.8(2) ?
C6 C26 C27 C28 -64.1(3) yes
C32 C27 C28 C29 -1.0(3) ?
C26 C27 C28 C29 179.9(2) ?
C27 C28 C29 C30 .5(3) ?
C28 C29 C30 C31 .6(4) ?
C29 C30 C31 C32 -1.1(4) ?
C33 O4 C32 C31 15.4(3) ?
C33 O4 C32 C27 -163.81(18) yes
C30 C31 C32 O4 -178.5(2) ?
C30 C31 C32 C27 .6(3) ?
C28 C27 C32 O4 179.66(18) ?
C26 C27 C32 O4 -1.3(3) ?
C28 C27 C32 C31 .4(3) ?
C26 C27 C32 C31 179.5(2) ?
