#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/03/2200331.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_2200331
loop_
_publ_author_name
'Kubicki, Maciej'
'Codding, Penelope W.'
_publ_section_title
;
 8-Oxa-1-aza-7-phenylbicyclo[5.2.1]decane-9,10-dione
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o406
_journal_page_last               o407
_journal_paper_doi               10.1107/S160053680100558X
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C14 H15 N O3'
_chemical_formula_sum            'C14 H15 N O3'
_chemical_formula_weight         245.27
_chemical_name_systematic
;
8-Oxa-1-aza-7-phenylbicyclo[5.2.1]decane-9,10-dione
;
_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                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.7112(8)
_cell_length_b                   10.4414(8)
_cell_length_c                   17.687(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      10
_cell_volume                     1239.4(2)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software'
_computing_data_reduction        'ENPROC (Rettig, 1978)'
_computing_molecular_graphics
'Stereochemical Workstation Operation Manual (Siemens, 1989)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .983
_diffrn_measured_fraction_theta_max .983
_diffrn_measurement_device_type  'CAD-4F four-circle'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  Ni-filter
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  .0000
_diffrn_reflns_av_sigmaI/netI    .0602
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1472
_diffrn_reflns_theta_full        74.96
_diffrn_reflns_theta_max         74.96
_diffrn_reflns_theta_min         4.92
_diffrn_standards_decay_%        3
_diffrn_standards_interval_time  33
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    .760
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          .25
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .1
_refine_diff_density_max         .182
_refine_diff_density_min         -.177
_refine_ls_extinction_coef       .0043(8)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1472
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          .0744
_refine_ls_R_factor_gt           .0628
_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)+(0.01P)²+0.6P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1369
_reflns_number_gt                1199
_reflns_number_total             1472
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            om6011.cif
_cod_data_source_block           I
_cod_database_code               2200331
_cod_database_fobs_code          2200331
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 .0144(5) .2640(3) .86377(19) .0510(8) Uani d . 1 . . N
C2 .0850(7) .3872(4) .8327(3) .0621(12) Uani d . 1 . . C
H21 .1103 .4470 .8735 .081 Uiso calc R 1 . . H
H22 -.0161 .4236 .7999 .081 Uiso calc R 1 . . H
C3 .2745(8) .3645(4) .7883(2) .0652(12) Uani d . 1 . . C
H31 .3350 .4468 .7773 .085 Uiso calc R 1 . . H
H32 .2399 .3250 .7404 .085 Uiso calc R 1 . . H
C4 .4287(7) .2803(4) .8280(3) .0658(12) Uani d . 1 . . C
H41 .4284 .3023 .8813 .086 Uiso calc R 1 . . H
H42 .5591 .3023 .8082 .086 Uiso calc R 1 . . H
C5 .4021(8) .1332(4) .8212(2) .0630(12) Uani d . 1 . . C
H51 .3067 .1172 .7811 .082 Uiso calc R 1 . . H
H52 .5285 .0975 .8049 .082 Uiso calc R 1 . . H
C6 .3337(8) .0574(4) .8913(2) .0575(11) Uani d . 1 . . C
H61 .3562 -.0329 .8815 .075 Uiso calc R 1 . . H
H62 .4185 .0815 .9334 .075 Uiso calc R 1 . . H
C7 .1171(7) .0740(3) .9160(2) .0474(10) Uani d . 1 . . C
C71 .0491(8) -.0121(3) .9802(2) .0578(12) Uani d . 1 . . C
C72 .1773(11) -.0245(5) 1.0421(2) .0839(18) Uani d . 1 . . C
H72 .2983 .0188 1.0432 .101 Uiso calc R 1 . . H
C73 .1203(15) -.1031(5) 1.1023(3) .112(3) Uani d . 1 . . C
H73 .2041 -.1137 1.1437 .134 Uiso calc R 1 . . H
C74 -.0623(13) -.1653(5) 1.0998(3) .104(3) Uani d . 1 . . C
H74 -.1022 -.2158 1.1404 .125 Uiso calc R 1 . . H
C75 -.1825(10) -.1531(5) 1.0391(3) .0907(18) Uani d . 1 . . C
H75 -.3032 -.1968 1.0376 .109 Uiso calc R 1 . . H
C76 -.1271(9) -.0759(4) .9791(3) .0734(14) Uani d . 1 . . C
H76 -.2114 -.0676 .9377 .088 Uiso calc R 1 . . H
O8 -.0105(5) .0538(2) .85033(15) .0568(8) Uani d . 1 . . O
C9 -.0398(6) .1662(4) .8152(2) .0555(10) Uani d . 1 . . C
O9 -.1123(6) .1764(3) .75395(17) .0788(11) Uani d . 1 . . O
C10 .0909(6) .2164(3) .9297(2) .0468(9) Uani d . 1 . . C
O10 .1485(5) .2767(2) .98398(14) .0628(9) Uani d . 1 . . O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0181 .0091 '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 .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0492 .0322 '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
C10 N1 C9 111.1(3) y
C10 N1 C2 120.9(4) y
C9 N1 C2 119.8(3) y
N1 C2 C3 109.1(3) ?
N1 C2 H21 109.9 ?
C3 C2 H21 109.9 ?
N1 C2 H22 109.9 ?
C3 C2 H22 109.9 ?
H21 C2 H22 108.3 ?
C2 C3 C4 114.9(3) ?
C2 C3 H31 108.5 ?
C4 C3 H31 108.5 ?
C2 C3 H32 108.5 ?
C4 C3 H32 108.5 ?
H31 C3 H32 107.5 ?
C3 C4 C5 117.1(4) ?
C3 C4 H41 108.0 ?
C5 C4 H41 108.0 ?
C3 C4 H42 108.0 ?
C5 C4 H42 108.0 ?
H41 C4 H42 107.3 ?
C6 C5 C4 118.7(4) ?
C6 C5 H51 107.6 ?
C4 C5 H51 107.6 ?
C6 C5 H52 107.6 ?
C4 C5 H52 107.6 ?
H51 C5 H52 107.1 ?
C7 C6 C5 117.1(4) ?
C7 C6 H61 108.0 ?
C5 C6 H61 108.0 ?
C7 C6 H62 108.0 ?
C5 C6 H62 108.0 ?
H61 C6 H62 107.3 ?
O8 C7 C10 101.6(3) ?
O8 C7 C71 109.5(3) ?
C10 C7 C71 115.2(3) ?
O8 C7 C6 108.3(3) ?
C10 C7 C6 105.5(3) ?
C71 C7 C6 115.6(4) ?
C76 C71 C72 120.1(4) ?
C76 C71 C7 122.8(4) ?
C72 C71 C7 117.1(4) ?
C73 C72 C71 118.8(6) ?
C73 C72 H72 120.6 ?
C71 C72 H72 120.6 ?
C74 C73 C72 119.5(7) ?
C74 C73 H73 120.2 ?
C72 C73 H73 120.2 ?
C75 C74 C73 120.6(5) ?
C75 C74 H74 119.7 ?
C73 C74 H74 119.7 ?
C74 C75 C76 120.3(6) ?
C74 C75 H75 119.8 ?
C76 C75 H75 119.8 ?
C71 C76 C75 120.6(5) ?
C71 C76 H76 119.7 ?
C75 C76 H76 119.7 ?
C9 O8 C7 109.2(3) y
O9 C9 O8 123.9(4) ?
O9 C9 N1 127.3(4) ?
O8 C9 N1 108.7(3) ?
O10 C10 N1 127.3(3) ?
O10 C10 C7 126.8(4) ?
N1 C10 C7 105.3(3) ?
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 C10 . 1.368(5) y
N1 C9 . 1.383(5) y
N1 C2 . 1.477(5) y
C2 C3 . 1.513(6) ?
C2 H21 . .9700 ?
C2 H22 . .9700 ?
C3 C4 . 1.529(6) ?
C3 H31 . .9700 ?
C3 H32 . .9700 ?
C4 C5 . 1.551(6) ?
C4 H41 . .9700 ?
C4 H42 . .9700 ?
C5 C6 . 1.541(5) ?
C5 H51 . .9700 ?
C5 H52 . .9700 ?
C6 C7 . 1.528(6) ?
C6 H61 . .9700 ?
C6 H62 . .9700 ?
C7 O8 . 1.459(4) y
C7 C10 . 1.517(5) ?
C7 C71 . 1.519(5) y
C71 C76 . 1.357(7) ?
C71 C72 . 1.398(7) ?
C72 C73 . 1.398(7) ?
C72 H72 . .9300 ?
C73 C74 . 1.387(11) ?
C73 H73 . .9300 ?
C74 C75 . 1.349(8) ?
C74 H74 . .9300 ?
C75 C76 . 1.384(7) ?
C75 H75 . .9300 ?
C76 H76 . .9300 ?
O8 C9 . 1.342(5) y
C9 O9 . 1.193(5) y
C10 O10 . 1.211(4) y
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
C6 H62 O10 4_557 .97 2.59 3.512(5) 158.5
C74 H74 O9 2_455 .93 2.81 3.495(7) 131.7
C4 H42 O9 1_655 .97 2.74 3.519(6) 137.7
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
C10 N1 C2 C3 83.1(4)
C9 N1 C2 C3 -62.5(5)
N1 C2 C3 C4 -46.3(5)
C2 C3 C4 C5 83.4(5)
C3 C4 C5 C6 -108.2(5)
C4 C5 C6 C7 71.8(6)
C5 C6 C7 O8 50.7(4)
C5 C6 C7 C10 -57.4(4)
C5 C6 C7 C71 174.0(3)
O8 C7 C71 C76 -12.2(5)
C10 C7 C71 C76 101.5(5)
C6 C7 C71 C76 -134.9(4)
O8 C7 C71 C72 167.6(4)
C10 C7 C71 C72 -78.7(5)
C6 C7 C71 C72 44.9(5)
C76 C71 C72 C73 -.1(7)
C7 C71 C72 C73 -179.9(5)
C71 C72 C73 C74 -1.0(8)
C72 C73 C74 C75 1.7(9)
C73 C74 C75 C76 -1.5(9)
C72 C71 C76 C75 .3(7)
C7 C71 C76 C75 -179.9(4)
C74 C75 C76 C71 .4(8)
C10 C7 O8 C9 20.6(4)
C71 C7 O8 C9 142.9(3)
C6 C7 O8 C9 -90.2(4)
C7 O8 C9 O9 168.2(4)
C7 O8 C9 N1 -15.9(5)
C10 N1 C9 O9 179.3(4)
C2 N1 C9 O9 -32.0(7)
C10 N1 C9 O8 3.5(5)
C2 N1 C9 O8 152.3(4)
C9 N1 C10 O10 -178.6(4)
C2 N1 C10 O10 33.1(6)
C9 N1 C10 C7 9.6(5)
C2 N1 C10 C7 -138.7(4)
O8 C7 C10 O10 170.4(4)
C71 C7 C10 O10 52.2(6)
C6 C7 C10 O10 -76.7(5)
O8 C7 C10 N1 -17.8(4)
C71 C7 C10 N1 -136.0(4)
C6 C7 C10 N1 95.2(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 23136138
