#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/01/2230106.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_2230106
loop_
_publ_author_name
'Moosa, Basem A.'
'Fazal, Atif'
'Ali, Shaikh A.'
'Fettouhi, Mohammed'
_publ_section_title
;
 Racemic methyl
 3,10-dioxa-2-azatricyclo[6.2.1.0^2,6^]undecane-4-carboxylate
;
_journal_coeditor_code           OM2422
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1245
_journal_paper_doi               10.1107/S160053681101484X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C10 H15 N O4'
_chemical_formula_moiety         'C10 H15 N O4'
_chemical_formula_sum            'C10 H15 N O4'
_chemical_formula_weight         213.23
_chemical_name_systematic
;
methyl 3,10-dioxa-2-azatricyclo[6.2.1.0^2,6^]undecane-4-carboxylate
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.546(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.213(3)
_cell_length_b                   7.1075(18)
_cell_length_c                   12.910(3)
_cell_measurement_reflns_used    13498
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.38
_cell_measurement_theta_min      1.82
_cell_volume                     1028.5(4)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'SMART (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART APEX area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13498
_diffrn_reflns_theta_full        28.38
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9947
_exptl_absorpt_correction_T_min  0.9790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.217
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2563
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0568
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0701P)²+0.2128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1547
_reflns_number_gt                1567
_reflns_number_total             2563
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2422.cif
_cod_data_source_block           I
_cod_original_cell_volume        1028.4(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230106
_cod_database_fobs_code          2230106
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_type_symbol
_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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.14231(14) 0.9997(2) 0.39231(12) 0.0433(4) Uani d . 1 1 . .
O O1 0.43183(15) 0.7626(3) 0.60910(14) 0.0821(6) Uani d . 1 1 . .
O O2 0.24093(17) 0.6880(3) 0.59172(15) 0.0838(6) Uani d . 1 1 . .
O O3 0.23751(14) 0.86158(19) 0.40074(11) 0.0559(4) Uani d . 1 1 . .
O O4 0.26276(13) 1.22561(19) 0.29897(11) 0.0516(4) Uani d . 1 1 . .
C C1 0.4428(3) 0.6375(5) 0.6972(2) 0.0950(11) Uani d . 1 1 . .
H H1A 0.3834 0.6687 0.7465 0.142 Uiso calc R 1 1 . .
H H1B 0.5207 0.6507 0.7290 0.142 Uiso calc R 1 1 . .
H H1C 0.4316 0.5099 0.6745 0.142 Uiso calc R 1 1 . .
C C2 0.3263(2) 0.7726(3) 0.56322(17) 0.0514(5) Uani d . 1 1 . .
C C3 0.3243(2) 0.9186(3) 0.47749(16) 0.0484(5) Uani d . 1 1 . .
C C4 0.2854(2) 1.1087(3) 0.51816(18) 0.0508(5) Uani d . 1 1 . .
C C5 0.15285(19) 1.1108(3) 0.48841(15) 0.0458(5) Uani d . 1 1 . .
C C6 0.0935(2) 1.3043(3) 0.47755(17) 0.0515(5) Uani d . 1 1 . .
C C7 0.1024(2) 1.3900(3) 0.36965(17) 0.0535(6) Uani d . 1 1 . .
C C8 0.0548(2) 1.2468(3) 0.29092(19) 0.0542(6) Uani d . 1 1 . .
C C9 0.15798(18) 1.1088(3) 0.29848(15) 0.0441(5) Uani d . 1 1 . .
C C10 0.2287(2) 1.4113(3) 0.3337(2) 0.0565(6) Uani d . 1 1 . .
H H4 0.400(2) 0.929(3) 0.4479(16) 0.056(6) Uiso d . 1 1 . .
H H5 0.3284(19) 1.202(3) 0.4850(17) 0.050(6) Uiso d . 1 1 . .
H H6 0.301(2) 1.116(3) 0.590(2) 0.069(7) Uiso d . 1 1 . .
H H7 0.1119(18) 1.042(3) 0.5399(16) 0.049(6) Uiso d . 1 1 . .
H H8 0.011(2) 1.290(3) 0.4920(18) 0.053(6) Uiso d . 1 1 . .
H H9 0.1310(19) 1.383(3) 0.5271(17) 0.051(6) Uiso d . 1 1 . .
H H10 0.061(2) 1.508(4) 0.3653(17) 0.061(6) Uiso d . 1 1 . .
H H11 -0.020(2) 1.189(3) 0.3108(17) 0.060(7) Uiso d . 1 1 . .
H H12 0.050(2) 1.304(4) 0.220(2) 0.073(7) Uiso d . 1 1 . .
H H13 0.1645(16) 1.018(3) 0.2423(15) 0.041(5) Uiso d . 1 1 . .
H H14 0.235(2) 1.501(4) 0.2774(19) 0.072(7) Uiso d . 1 1 . .
H H15 0.284(2) 1.451(3) 0.3903(18) 0.056(6) Uiso d . 1 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 N1 C9 . . 108.55(14) ?
O3 N1 C5 . . 104.91(14) ?
C9 N1 C5 . . 114.04(16) ?
C2 O1 C1 . . 116.43(19) ?
C3 O3 N1 . . 110.24(14) ?
C9 O4 C10 . . 107.76(15) ?
O1 C1 H1A . . 109.5 ?
O1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
O1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O2 C2 O1 . . 123.6(2) ?
O2 C2 C3 . . 124.9(2) ?
O1 C2 C3 . . 111.22(19) ?
O3 C3 C2 . . 107.94(18) ?
O3 C3 C4 . . 107.17(17) ?
C2 C3 C4 . . 110.81(18) ?
O3 C3 H4 . . 110.3(13) ?
C2 C3 H4 . . 110.7(13) ?
C4 C3 H4 . . 109.9(13) ?
C3 C4 C5 . . 102.07(17) ?
C3 C4 H5 . . 108.5(13) ?
C5 C4 H5 . . 113.0(13) ?
C3 C4 H6 . . 110.0(15) ?
C5 C4 H6 . . 113.8(15) ?
H5 C4 H6 . . 109(2) ?
N1 C5 C4 . . 105.22(16) ?
N1 C5 C6 . . 112.30(17) ?
C4 C5 C6 . . 116.70(19) ?
N1 C5 H7 . . 106.4(12) ?
C4 C5 H7 . . 107.7(13) ?
C6 C5 H7 . . 107.9(12) ?
C7 C6 C5 . . 113.74(17) ?
C7 C6 H8 . . 107.9(14) ?
C5 C6 H8 . . 108.0(13) ?
C7 C6 H9 . . 110.1(13) ?
C5 C6 H9 . . 106.8(13) ?
H8 C6 H9 . . 110.3(19) ?
C10 C7 C8 . . 100.20(18) ?
C10 C7 C6 . . 113.9(2) ?
C8 C7 C6 . . 108.17(19) ?
C10 C7 H10 . . 110.8(13) ?
C8 C7 H10 . . 112.4(14) ?
C6 C7 H10 . . 110.9(13) ?
C9 C8 C7 . . 97.78(18) ?
C9 C8 H11 . . 111.8(14) ?
C7 C8 H11 . . 113.3(13) ?
C9 C8 H12 . . 110.2(14) ?
C7 C8 H12 . . 110.5(15) ?
H11 C8 H12 . . 112(2) ?
O4 C9 N1 . . 114.92(16) ?
O4 C9 C8 . . 104.39(17) ?
N1 C9 C8 . . 106.81(17) ?
O4 C9 H13 . . 108.0(11) ?
N1 C9 H13 . . 106.1(11) ?
C8 C9 H13 . . 117.0(11) ?
O4 C10 C7 . . 105.13(18) ?
O4 C10 H14 . . 110.0(15) ?
C7 C10 H14 . . 112.6(15) ?
O4 C10 H15 . . 108.9(13) ?
C7 C10 H15 . . 112.1(13) ?
H14 C10 H15 . . 108(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
N1 O3 . 1.452(2) ?
N1 C9 . 1.453(2) ?
N1 C5 . 1.473(2) ?
O1 C2 . 1.311(3) ?
O1 C1 . 1.446(3) ?
O2 C2 . 1.197(3) ?
O3 C3 . 1.429(3) ?
O4 C9 . 1.439(2) ?
O4 C10 . 1.449(3) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C3 . 1.517(3) ?
C3 C4 . 1.518(3) ?
C3 H4 . 0.95(2) ?
C4 C5 . 1.525(3) ?
C4 H5 . 0.93(2) ?
C4 H6 . 0.94(3) ?
C5 C6 . 1.532(3) ?
C5 H7 . 0.95(2) ?
C6 C7 . 1.526(3) ?
C6 H8 . 0.95(2) ?
C6 H9 . 0.94(2) ?
C7 C10 . 1.509(3) ?
C7 C8 . 1.525(3) ?
C7 H10 . 0.96(2) ?
C8 C9 . 1.518(3) ?
C8 H11 . 0.98(2) ?
C8 H12 . 1.01(3) ?
C9 H13 . 0.976(19) ?
C10 H14 . 0.97(3) ?
C10 H15 . 0.99(2) ?
