#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:53:49 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178410 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/31/4023168.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4023168
loop_
_publ_author_name
'Yit Wooi Goh'
'Brett R. Pool'
'Jonathan M. White'
_publ_section_title
;
 Structural Studies on Cycloadducts of Furan, 2-Methoxyfuran,
 and 5-Trimethylsilylcyclopentadiene with Maleic Anhydride
 and N-Methylmaleimide
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              151
_journal_page_last               156
_journal_paper_doi               10.1021/jo7018575
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C12 H19 N O6'
_chemical_formula_weight         273.28
_chemical_name_systematic
;
 ?
;
_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                 98.569(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8817(8)
_cell_length_b                   8.1183(7)
_cell_length_c                   17.2401(15)
_cell_measurement_reflns_used    3721
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.32
_cell_volume                     1229.21(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6234
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.119
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0005(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0484P)²+0.8107P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1228
_reflns_number_gt                1886
_reflns_number_total             2158
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7018575-File001_10.cif
_cod_data_source_block           CMPD22
_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 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023168
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6098(2) 0.4268(2) 0.15389(11) 0.0312(4) Uani 1 1 d . . .
C2 C 0.6808(2) 0.5900(2) 0.18080(11) 0.0299(4) Uani 1 1 d . . .
H2 H 0.7917 0.5811 0.1941 0.036 Uiso 1 1 calc R . .
C3 C 0.6338(2) 0.7396(2) 0.12505(11) 0.0298(4) Uani 1 1 d . . .
C4 C 0.4651(2) 0.7281(2) 0.09686(11) 0.0309(4) Uani 1 1 d . . .
H4 H 0.4174 0.7014 0.0467 0.037 Uiso 1 1 calc R . .
C5 C 0.4000(2) 0.7640(2) 0.15860(12) 0.0354(5) Uani 1 1 d . . .
H5 H 0.2961 0.7652 0.1610 0.042 Uiso 1 1 calc R . .
C6 C 0.5261(2) 0.8025(2) 0.22429(12) 0.0356(5) Uani 1 1 d . . .
H6 H 0.4973 0.8724 0.2660 0.043 Uiso 1 1 calc R . .
C7 C 0.6065(2) 0.6364(2) 0.25255(11) 0.0317(4) Uani 1 1 d . . .
H7 H 0.6827 0.6523 0.2993 0.038 Uiso 1 1 calc R . .
C8 C 0.5005(2) 0.4963(2) 0.26311(11) 0.0306(4) Uani 1 1 d . . .
C9 C 0.4138(3) 0.2357(3) 0.19312(13) 0.0425(5) Uani 1 1 d . . .
H9A H 0.3519 0.2293 0.2342 0.064 Uiso 0.50 1 calc PR . .
H9B H 0.4779 0.1402 0.1950 0.064 Uiso 0.50 1 calc PR . .
H9C H 0.3495 0.2404 0.1432 0.064 Uiso 0.50 1 calc PR . .
H9D H 0.4343 0.1773 0.1474 0.064 Uiso 0.50 1 calc PR . .
H9E H 0.3082 0.2664 0.1866 0.064 Uiso 0.50 1 calc PR . .
H9F H 0.4367 0.1662 0.2384 0.064 Uiso 0.50 1 calc PR . .
C10 C 0.6939(3) 0.9032(3) 0.02222(13) 0.0466(6) Uani 1 1 d . . .
H10A H 0.7676 0.9151 -0.0129 0.070 Uiso 1 1 calc R . .
H10B H 0.6921 1.0016 0.0530 0.070 Uiso 1 1 calc R . .
H10C H 0.5951 0.8850 -0.0075 0.070 Uiso 1 1 calc R . .
N1 N 0.50800(18) 0.38353(19) 0.20371(9) 0.0312(4) Uani 1 1 d . . .
O1 O 0.63516(18) 0.34460(18) 0.09881(8) 0.0431(4) Uani 1 1 d . . .
O2 O 0.41852(18) 0.48238(18) 0.31290(8) 0.0440(4) Uani 1 1 d . . .
O3 O 0.64044(15) 0.87023(16) 0.18269(8) 0.0361(4) Uani 1 1 d . . .
O5 O 0.73440(15) 0.76534(17) 0.07328(8) 0.0370(4) Uani 1 1 d . . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 124.30(19) . . ?
O1 C1 C2 127.38(18) . . ?
N1 C1 C2 108.32(16) . . ?
C1 C2 C7 104.66(15) . . ?
C1 C2 C3 115.52(15) . . ?
C7 C2 C3 101.36(14) . . ?
C1 C2 H2 111.5 . . ?
C7 C2 H2 111.5 . . ?
C3 C2 H2 111.5 . . ?
O5 C3 O3 111.82(15) . . ?
O5 C3 C4 120.86(16) . . ?
O3 C3 C4 101.76(14) . . ?
O5 C3 C2 112.20(15) . . ?
O3 C3 C2 99.61(13) . . ?
C4 C3 C2 108.09(15) . . ?
C5 C4 C3 105.11(17) . . ?
C5 C4 H4 127.4 . . ?
C3 C4 H4 127.4 . . ?
C4 C5 C6 106.68(17) . . ?
C4 C5 H5 126.7 . . ?
C6 C5 H5 126.7 . . ?
O3 C6 C5 101.92(15) . . ?
O3 C6 C7 99.28(15) . . ?
C5 C6 C7 107.99(15) . . ?
O3 C6 H6 115.2 . . ?
C5 C6 H6 115.2 . . ?
C7 C6 H6 115.2 . . ?
C8 C7 C2 105.31(15) . . ?
C8 C7 C6 115.04(16) . . ?
C2 C7 C6 101.02(14) . . ?
C8 C7 H7 111.6 . . ?
C2 C7 H7 111.6 . . ?
C6 C7 H7 111.6 . . ?
O2 C8 N1 124.32(17) . . ?
O2 C8 C7 127.54(17) . . ?
N1 C8 C7 108.11(15) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C9 H9D 109.5 . . ?
H9A C9 H9D 141.1 . . ?
H9B C9 H9D 56.3 . . ?
H9C C9 H9D 56.3 . . ?
N1 C9 H9E 109.5 . . ?
H9A C9 H9E 56.3 . . ?
H9B C9 H9E 141.1 . . ?
H9C C9 H9E 56.3 . . ?
H9D C9 H9E 109.5 . . ?
N1 C9 H9F 109.5 . . ?
H9A C9 H9F 56.3 . . ?
H9B C9 H9F 56.3 . . ?
H9C C9 H9F 141.1 . . ?
H9D C9 H9F 109.5 . . ?
H9E C9 H9F 109.5 . . ?
O5 C10 H10A 109.5 . . ?
O5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 N1 C8 113.58(16) . . ?
C1 N1 C9 123.21(16) . . ?
C8 N1 C9 123.18(17) . . ?
C6 O3 C3 95.89(13) . . ?
C3 O5 C10 112.96(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.209(2) . ?
C1 N1 1.382(2) . ?
C1 C2 1.510(3) . ?
C2 C7 1.533(3) . ?
C2 C3 1.567(2) . ?
C2 H2 0.9800 . ?
C3 O5 1.370(2) . ?
C3 O3 1.448(2) . ?
C3 C4 1.507(3) . ?
C4 C5 1.318(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.503(3) . ?
C5 H5 0.9300 . ?
C6 O3 1.437(2) . ?
C6 C7 1.569(3) . ?
C6 H6 0.9800 . ?
C7 C8 1.505(3) . ?
C7 H7 0.9800 . ?
C8 O2 1.211(2) . ?
C8 N1 1.382(2) . ?
C9 N1 1.459(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C9 H9D 0.9600 . ?
C9 H9E 0.9600 . ?
C9 H9F 0.9600 . ?
C10 O5 1.436(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C7 180.00(18) . . . . ?
N1 C1 C2 C7 -0.27(19) . . . . ?
O1 C1 C2 C3 69.5(2) . . . . ?
N1 C1 C2 C3 -110.79(17) . . . . ?
C1 C2 C3 O5 -93.70(19) . . . . ?
C7 C2 C3 O5 153.84(15) . . . . ?
C1 C2 C3 O3 147.85(15) . . . . ?
C7 C2 C3 O3 35.40(16) . . . . ?
C1 C2 C3 C4 42.0(2) . . . . ?
C7 C2 C3 C4 -70.43(17) . . . . ?
O5 C3 C4 C5 -157.66(17) . . . . ?
O3 C3 C4 C5 -33.14(18) . . . . ?
C2 C3 C4 C5 71.18(19) . . . . ?
C3 C4 C5 C6 1.6(2) . . . . ?
C4 C5 C6 O3 30.72(19) . . . . ?
C4 C5 C6 C7 -73.28(19) . . . . ?
C1 C2 C7 C8 1.05(18) . . . . ?
C3 C2 C7 C8 121.50(15) . . . . ?
C1 C2 C7 C6 -118.97(15) . . . . ?
C3 C2 C7 C6 1.47(17) . . . . ?
O3 C6 C7 C8 -151.09(15) . . . . ?
C5 C6 C7 C8 -45.2(2) . . . . ?
O3 C6 C7 C2 -38.27(17) . . . . ?
C5 C6 C7 C2 67.58(18) . . . . ?
C2 C7 C8 O2 -179.78(19) . . . . ?
C6 C7 C8 O2 -69.5(3) . . . . ?
C2 C7 C8 N1 -1.50(19) . . . . ?
C6 C7 C8 N1 108.78(18) . . . . ?
O1 C1 N1 C8 179.01(17) . . . . ?
C2 C1 N1 C8 -0.7(2) . . . . ?
O1 C1 N1 C9 -2.9(3) . . . . ?
C2 C1 N1 C9 177.34(17) . . . . ?
O2 C8 N1 C1 179.78(18) . . . . ?
C7 C8 N1 C1 1.4(2) . . . . ?
O2 C8 N1 C9 1.7(3) . . . . ?
C7 C8 N1 C9 -176.63(17) . . . . ?
C5 C6 O3 C3 -48.86(16) . . . . ?
C7 C6 O3 C3 61.89(15) . . . . ?
O5 C3 O3 C6 -179.64(15) . . . . ?
C4 C3 O3 C6 49.99(16) . . . . ?
C2 C3 O3 C6 -60.92(15) . . . . ?
O3 C3 O5 C10 -68.4(2) . . . . ?
C4 C3 O5 C10 51.2(2) . . . . ?
C2 C3 O5 C10 -179.41(16) . . . . ?
