#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2009114.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_2009114
loop_
_publ_author_name
'Billodeaux, D. R.'
'Fronczek, F. R.'
'D\"ur\"ust, Y.'
_publ_section_title
;
 2,6-Dimethylspiro[1-oxa-2,5-diazabicyclo[3.3.0]octane-3,1'-cyclohexane]-4,6-dione
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1943
_journal_page_last               1945
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C12 H18 N2 O3'
_chemical_formula_weight         238.28
_chemical_melting_point          400.5(5)
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2452(5)
_cell_length_b                   7.8690(6)
_cell_length_c                   24.1510(14)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    297
_cell_measurement_theta_max      44.1
_cell_measurement_theta_min      21.6
_cell_volume                     1186.86(15)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1993)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1996)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0130
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            1444
_diffrn_reflns_theta_full        75.0
_diffrn_reflns_theta_max         75
_diffrn_reflns_theta_min         3.66
_diffrn_standards_decay_%        3.9
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_correction_T_min  0.775
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.16
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.6(3)
_refine_ls_extinction_coef       0.0164(16)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1444
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.036
_refine_ls_R_factor_gt           0.034
_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/[\s^2^(Fo^2^)+(0.0738P)^2^+0.0956P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.106
_reflns_number_gt                1377
_reflns_number_total             1444
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    da1097.cif
_[local]_cod_data_source_block   A29
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '400-401' was changed to '400.5(5)' -
the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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        1186.90(10)
_cod_database_code               2009114
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_type_symbol
O1 0.5462(2) 0.37414(17) 0.43107(5) 0.0438(3) Uani d . 1 O
O9 0.8061(3) 0.6730(2) 0.46952(6) 0.0553(4) Uani d . 1 O
O10 0.2555(3) 0.8489(2) 0.36026(8) 0.0661(5) Uani d . 1 O
N2 0.3706(3) 0.29354(19) 0.40122(6) 0.0422(4) Uani d . 1 N
N6 0.5624(3) 0.7874(2) 0.40892(7) 0.0449(4) Uani d . 1 N
C3 0.2750(3) 0.4379(2) 0.37047(7) 0.0373(4) Uani d . 1 C
C4 0.2839(3) 0.5858(2) 0.41381(8) 0.0412(4) Uani d . 1 C
H4 0.1480 0.5963 0.4338 0.049 Uiso calc R 1 H
C5 0.3544(3) 0.7548(2) 0.39058(8) 0.0456(5) Uani d . 1 C
C7 0.6346(3) 0.6685(2) 0.44626(7) 0.0420(4) Uani d . 1 C
C8 0.4633(3) 0.5334(2) 0.45240(7) 0.0407(4) Uani d . 1 C
H8 0.4141 0.5228 0.4908 0.049 Uiso calc R 1 H
C11 0.0461(3) 0.4030(3) 0.35130(9) 0.0503(5) Uani d . 1 C
H11A -0.0128 0.5058 0.3352 0.060 Uiso calc R 1 H
H11B -0.0409 0.3735 0.3832 0.060 Uiso calc R 1 H
C12 0.0334(4) 0.2589(3) 0.30865(10) 0.0631(6) Uani d . 1 C
H12A 0.0781 0.1531 0.3257 0.076 Uiso calc R 1 H
H12B -0.1135 0.2456 0.2963 0.076 Uiso calc R 1 H
C13 0.1758(5) 0.2969(3) 0.25927(10) 0.0685(7) Uani d . 1 C
H13A 0.1230 0.3970 0.2402 0.082 Uiso calc R 1 H
H13B 0.1712 0.2023 0.2336 0.082 Uiso calc R 1 H
C14 0.4063(4) 0.3270(3) 0.27777(8) 0.0554(5) Uani d . 1 C
H14A 0.4629 0.2239 0.2942 0.066 Uiso calc R 1 H
H14B 0.4937 0.3550 0.2458 0.066 Uiso calc R 1 H
C15 0.4178(3) 0.4712(2) 0.31975(7) 0.0439(4) Uani d . 1 C
H15A 0.3733 0.5762 0.3021 0.053 Uiso calc R 1 H
H15B 0.5649 0.4850 0.3318 0.053 Uiso calc R 1 H
C16 0.6862(4) 0.9353(3) 0.39222(10) 0.0599(6) Uani d . 1 C
H16A 0.6941 1.0141 0.4225 0.090 Uiso calc R 1 H
H16B 0.6181 0.9890 0.3612 0.090 Uiso calc R 1 H
H16C 0.8280 0.9004 0.3820 0.090 Uiso calc R 1 H
C17 0.2319(4) 0.2155(3) 0.44290(9) 0.0615(6) Uani d . 1 C
H17A 0.3141 0.1380 0.4651 0.092 Uiso calc R 1 H
H17B 0.1182 0.1549 0.4248 0.092 Uiso calc R 1 H
H17C 0.1723 0.3023 0.4662 0.092 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0428(7) 0.0418(6) 0.0466(7) 0.0048(6) -0.0058(6) -0.0015(5)
O9 0.0459(7) 0.0604(9) 0.0594(8) -0.0005(8) -0.0113(7) -0.0079(7)
O10 0.0707(11) 0.0435(8) 0.0842(10) 0.0091(8) -0.0254(10) 0.0036(7)
N2 0.0441(8) 0.0393(7) 0.0432(7) -0.0023(7) -0.0009(7) 0.0038(6)
N6 0.0439(9) 0.0400(8) 0.0508(8) -0.0015(7) -0.0023(7) -0.0027(7)
C3 0.0338(8) 0.0371(8) 0.0411(8) 0.0005(7) -0.0002(7) -0.0004(7)
C4 0.0354(8) 0.0430(9) 0.0453(8) 0.0025(8) 0.0020(8) -0.0045(7)
C5 0.0460(10) 0.0378(9) 0.0531(10) 0.0064(9) -0.0062(8) -0.0046(8)
C7 0.0419(9) 0.0452(9) 0.0390(8) 0.0039(8) 0.0011(7) -0.0077(7)
C8 0.0415(9) 0.0447(10) 0.0358(7) 0.0029(9) 0.0018(7) -0.0019(7)
C11 0.0357(9) 0.0522(11) 0.0630(11) -0.0008(9) -0.0065(9) -0.0034(9)
C12 0.0523(12) 0.0591(13) 0.0778(14) -0.0075(12) -0.0179(11) -0.0105(12)
C13 0.0790(17) 0.0699(15) 0.0567(11) 0.0007(15) -0.0187(12) -0.0166(11)
C14 0.0660(13) 0.0557(11) 0.0445(9) 0.0033(12) 0.0038(10) -0.0079(9)
C15 0.0483(10) 0.0439(9) 0.0395(8) -0.0017(9) 0.0040(8) 0.0011(7)
C16 0.0609(13) 0.0457(11) 0.0732(13) -0.0115(12) -0.0031(12) 0.0024(9)
C17 0.0696(15) 0.0559(12) 0.0591(11) -0.0122(12) 0.0057(12) 0.0154(10)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 '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'
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
C8 O1 N2 106.42(14) yes
O1 N2 C3 102.55(12) yes
O1 N2 C17 106.73(14) yes
C17 N2 C3 115.32(17) ?
C7 N6 C5 112.85(17) ?
C7 N6 C16 123.49(18) ?
C5 N6 C16 123.60(18) ?
N2 C3 C11 113.01(16) ?
N2 C3 C15 107.20(14) ?
C11 C3 C15 109.38(16) ?
N2 C3 C4 102.73(14) yes
C11 C3 C4 111.67(14) ?
C15 C3 C4 112.67(15) ?
C5 C4 C8 104.65(16) ?
C5 C4 C3 114.64(15) ?
C8 C4 C3 103.62(14) ?
O10 C5 N6 123.7(2) yes
O10 C5 C4 128.0(2) ?
N6 C5 C4 108.36(17) ?
O9 C7 N6 125.1(2) yes
O9 C7 C8 126.85(19) ?
N6 C7 C8 108.04(16) ?
O1 C8 C4 106.31(14) yes
O1 C8 C7 108.62(15) ?
C4 C8 C7 105.73(15) ?
C3 C11 C12 112.64(17) ?
C13 C12 C11 110.6(2) ?
C12 C13 C14 110.70(18) ?
C15 C14 C13 110.78(19) ?
C14 C15 C3 112.11(17) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N2 1.458(2) yes
O1 C8 1.451(2) yes
O9 C7 1.210(3) yes
O10 C5 1.210(2) yes
N2 C3 1.483(2) yes
N2 C17 1.464(3) yes
N6 C5 1.396(3) yes
N6 C7 1.375(2) yes
N6 C16 1.454(3) yes
C3 C11 1.528(2) ?
C3 C15 1.538(2) ?
C3 C4 1.566(2) ?
C4 C5 1.509(3) ?
C4 C8 1.514(3) ?
C7 C8 1.516(3) ?
C11 C12 1.534(3) ?
C12 C13 1.518(4) ?
C13 C14 1.526(4) ?
C14 C15 1.523(3) ?
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
C8 O1 N2 C17 -79.06(17) ?
C8 O1 N2 C3 42.57(15) yes
O1 N2 C3 C11 -160.57(14) ?
C17 N2 C3 C11 -45.0(2) ?
O1 N2 C3 C15 78.84(16) ?
C17 N2 C3 C15 -165.59(17) ?
O1 N2 C3 C4 -40.09(16) yes
C17 N2 C3 C4 75.48(18) yes
N2 C3 C4 C5 137.36(16) ?
C11 C3 C4 C5 -101.2(2) ?
C15 C3 C4 C5 22.3(2) ?
N2 C3 C4 C8 23.94(18) yes
C11 C3 C4 C8 145.34(16) ?
C15 C3 C4 C8 -91.08(18) ?
C7 N6 C5 O10 175.40(19) ?
C16 N6 C5 O10 -2.0(3) ?yes
C7 N6 C5 C4 -5.9(2) ?
C16 N6 C5 C4 176.61(18) ?
C8 C4 C5 O10 -175.5(2) ?
C3 C4 C5 O10 71.7(3) ?
C8 C4 C5 N6 5.96(19) ?
C3 C4 C5 N6 -106.85(18) ?
C5 N6 C7 O9 -177.05(17) ?
C16 N6 C7 O9 0.4(3) yes
C5 N6 C7 C8 3.3(2) ?
C16 N6 C7 C8 -179.28(18) ?
N2 O1 C8 C4 -26.77(17) yes
N2 O1 C8 C7 -140.13(14) ?
C5 C4 C8 O1 -119.30(15) yes
C3 C4 C8 O1 1.14(18) ?
C5 C4 C8 C7 -3.96(18) ?
C3 C4 C8 C7 116.48(15) ?
O9 C7 C8 O1 -65.2(2) ?
N6 C7 C8 O1 114.46(16) ?
O9 C7 C8 C4 -178.96(18) ?
N6 C7 C8 C4 0.71(19) ?
N2 C3 C11 C12 -64.9(2) ?
C15 C3 C11 C12 54.4(2) ?
C4 C3 C11 C12 179.83(17) yes
C3 C11 C12 C13 -56.2(3) yes
C11 C12 C13 C14 56.4(3) yes
C12 C13 C14 C15 -57.2(3) yes
C13 C14 C15 C3 56.8(2) yes
N2 C3 C15 C14 68.1(2) ?
C11 C3 C15 C14 -54.7(2) yes
C4 C3 C15 C14 -179.58(16) ?