#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:50:19 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180318 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/32/7153254.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_7153254
loop_
_publ_author_name
'Petrova, Tetyana'
'Tarabara, Igor'
'Palchikov, Vitaliy'
'Kasyan, Liliya'
'Kosenkov, Dmytro'
'Okovytyy, Sergiy'
'Gorb, Leonid'
'Shishkina, Svetlana'
'Shishkin, Oleg'
'Leszczynski, Jerzy'
_publ_section_title
;
 Ethanolysis of N-substituted norbornane epoxyimides: discovery of diverse
 pathways depending on substituent's character.
;
_journal_issue                   9
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2142
_journal_page_last               2157
_journal_paper_doi               10.1039/b917850c
_journal_volume                  8
_journal_year                    2010
_chemical_formula_moiety         'C10 H13 N O4'
_chemical_formula_sum            'C10 H13 N O4'
_chemical_formula_weight         211.21
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.676(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2977(16)
_cell_length_b                   6.6557(9)
_cell_length_c                   13.778(2)
_cell_measurement_reflns_used    3258
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32
_cell_measurement_theta_min      4
_cell_volume                     962.8(3)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr 1 2005,17:53:34)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr 1 2005,17:53:34)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr 1 2005,17:53:34)
;
_computing_molecular_graphics    'XP (Siemens, 1998)'
_computing_publication_material  'SHELXTL (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 1998)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  Xcalibur"3
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0138
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4738
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.05
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0353
_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)+(0.0583P)²+0.1505P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.0994
_reflns_number_gt                1874
_reflns_number_total             2154
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b917850c.txt
_cod_data_source_block           KAS29
_cod_original_cell_volume        962.8(2)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7153254
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
N1 N 0.22091(9) 0.47728(15) 0.18930(7) 0.0269(2) Uani 1 1 d
O1 O 0.04648(8) 0.27139(13) 0.11949(6) 0.0359(2) Uani 1 1 d
O2 O 0.41356(8) 0.61949(15) 0.28803(7) 0.0435(3) Uani 1 1 d
O3 O 0.07674(8) 0.43697(15) 0.33119(7) 0.0371(2) Uani 1 1 d
H3O H 0.0509(18) 0.536(3) 0.3583(14) 0.060(5) Uiso 1 1 d
O4 O 0.32526(9) 0.42670(17) 0.57609(7) 0.0435(3) Uani 1 1 d
H4O H 0.406(2) 0.427(3) 0.6111(15) 0.062(5) Uiso 1 1 d
C1 C 0.15167(10) 0.30234(17) 0.18585(8) 0.0267(2) Uani 1 1 d
C2 C 0.23267(11) 0.16305(17) 0.27135(8) 0.0283(3) Uani 1 1 d
H2 H 0.2432(14) 0.032(2) 0.2406(12) 0.043(4) Uiso 1 1 d
C3 C 0.19312(11) 0.12141(18) 0.36606(9) 0.0305(3) Uani 1 1 d
H3 H 0.1282(15) 0.014(3) 0.3526(12) 0.048(4) Uiso 1 1 d
C4 C 0.16485(10) 0.31848(19) 0.41175(8) 0.0286(3) Uani 1 1 d
H4 H 0.1314(14) 0.290(2) 0.4669(12) 0.038(4) Uiso 1 1 d
C5 C 0.29835(10) 0.41682(18) 0.46599(8) 0.0279(3) Uani 1 1 d
H5 H 0.2978(13) 0.555(2) 0.4366(11) 0.034(4) Uiso 1 1 d
C6 C 0.38763(10) 0.26999(17) 0.44045(8) 0.0275(2) Uani 1 1 d
H6 H 0.4790(14) 0.289(2) 0.4842(11) 0.036(4) Uiso 1 1 d
C7 C 0.32530(12) 0.06725(19) 0.44854(10) 0.0355(3) Uani 1 1 d
H7B H 0.3237(15) 0.042(2) 0.5212(12) 0.047(4) Uiso 1 1 d
H7A H 0.3664(16) -0.045(3) 0.4278(13) 0.050(4) Uiso 1 1 d
C8 C 0.36171(10) 0.27396(18) 0.32159(9) 0.0284(3) Uani 1 1 d
H8 H 0.4308(15) 0.207(2) 0.3051(12) 0.044(4) Uiso 1 1 d
C9 C 0.33988(10) 0.47646(18) 0.26801(8) 0.0284(2) Uani 1 1 d
C10 C 0.16645(13) 0.6502(2) 0.12283(10) 0.0356(3) Uani 1 1 d
H10C H 0.1094(16) 0.601(2) 0.0541(13) 0.051(5) Uiso 1 1 d
H10B H 0.1121(18) 0.727(3) 0.1517(14) 0.061(5) Uiso 1 1 d
H10A H 0.2372(17) 0.732(3) 0.1241(13) 0.051(5) Uiso 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
C9 N1 C1 113.25(9)
C9 N1 C10 124.00(10)
C1 N1 C10 122.46(10)
O1 C1 N1 123.08(10)
O1 C1 C2 128.45(11)
N1 C1 C2 108.36(9)
C1 C2 C8 104.74(9)
C1 C2 C3 119.01(10)
C8 C2 C3 102.99(9)
C4 C3 C7 100.83(9)
C4 C3 C2 111.07(9)
C7 C3 C2 99.18(9)
O3 C4 C3 110.13(9)
O3 C4 C5 114.53(10)
C3 C4 C5 104.11(9)
O4 C5 C6 111.77(9)
O4 C5 C4 108.42(9)
C6 C5 C4 102.95(9)
C5 C6 C7 100.59(9)
C5 C6 C8 110.28(9)
C7 C6 C8 100.22(9)
C6 C7 C3 94.90(9)
C9 C8 C2 104.44(9)
C9 C8 C6 117.58(10)
C2 C8 C6 104.04(9)
O2 C9 N1 123.80(11)
O2 C9 C8 127.36(10)
N1 C9 C8 108.83(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C9 1.3806(14)
N1 C1 1.3937(15)
N1 C10 1.4578(15)
O1 C1 1.2199(14)
O2 C9 1.2270(15)
O3 C4 1.4243(14)
O4 C5 1.4344(14)
C1 C2 1.5128(16)
C2 C8 1.5504(16)
C2 C3 1.5524(16)
C3 C4 1.5386(17)
C3 C7 1.5485(17)
C4 C5 1.5585(16)
C5 C6 1.5357(15)
C6 C7 1.5450(17)
C6 C8 1.5538(15)
C8 C9 1.5126(17)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3O O1 0.86(2) 2.00(2) 2.8377(13) 163.7(17) 2
O4 H4O O2 0.86(2) 2.03(2) 2.8680(14) 167.3(18) 3_666
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
C9 N1 C1 O1 -177.19(10)
C10 N1 C1 O1 8.76(17)
C9 N1 C1 C2 -0.72(12)
C10 N1 C1 C2 -174.77(10)
O1 C1 C2 C8 173.10(11)
N1 C1 C2 C8 -3.13(11)
O1 C1 C2 C3 -72.59(15)
N1 C1 C2 C3 111.18(11)
C1 C2 C3 C4 -49.01(13)
C8 C2 C3 C4 66.24(11)
C1 C2 C3 C7 -154.44(10)
C8 C2 C3 C7 -39.19(11)
C7 C3 C4 O3 156.10(9)
C2 C3 C4 O3 51.76(12)
C7 C3 C4 C5 32.87(11)
C2 C3 C4 C5 -71.47(11)
O3 C4 C5 O4 123.93(10)
C3 C4 C5 O4 -115.76(10)
O3 C4 C5 C6 -117.53(10)
C3 C4 C5 C6 2.78(11)
O4 C5 C6 C7 78.61(11)
C4 C5 C6 C7 -37.55(10)
O4 C5 C6 C8 -176.23(9)
C4 C5 C6 C8 67.61(11)
C5 C6 C7 C3 57.05(10)
C8 C6 C7 C3 -56.03(10)
C4 C3 C7 C6 -54.95(10)
C2 C3 C7 C6 58.73(10)
C1 C2 C8 C9 5.41(11)
C3 C2 C8 C9 -119.71(9)
C1 C2 C8 C6 129.27(9)
C3 C2 C8 C6 4.15(11)
C5 C6 C8 C9 41.98(13)
C7 C6 C8 C9 147.39(10)
C5 C6 C8 C2 -72.90(11)
C7 C6 C8 C2 32.51(10)
C1 N1 C9 O2 -176.21(11)
C10 N1 C9 O2 -2.27(17)
C1 N1 C9 C8 4.42(12)
C10 N1 C9 C8 178.37(10)
C2 C8 C9 O2 174.61(11)
C6 C8 C9 O2 59.96(15)
C2 C8 C9 N1 -6.05(11)
C6 C8 C9 N1 -120.71(10)
