#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:56:18 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178412 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/33/4023362.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_4023362
loop_
_publ_author_name
'Petr Melša'
'Michal Čajan'
'Zdeněk Havlas'
'Ctibor Mazal'
_publ_section_title
;
 Substituent Effect on exo Stereoselectivity in the 1,3-Dipolar
 Cycloaddition Reaction of Tulipalin A with Nitrile Ylides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3032
_journal_page_last               3039
_journal_paper_doi               10.1021/jo702563n
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C19 H17 N O2'
_chemical_formula_weight         291.34
_chemical_name_systematic
; 
 (5S*,6S*)-6,8-Diphenyl-2-oxa-7-azaspiro[4.4]non-7-en-1-one  
;
_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                 100.66(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8997(12)
_cell_length_b                   26.612(5)
_cell_length_c                   9.3887(19)
_cell_measurement_reflns_used    710
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      21.499
_cell_measurement_theta_min      2.708
_cell_volume                     1448.6(5)
_computing_cell_refinement       'KUMA KM-4 software'
_computing_data_collection       'KUMA KM-4 Crysalis V170'
_computing_data_reduction        'KUMA KM-4 software'
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  'SHELXTL (Bruker, 1998)'
_computing_structure_refinement  'SHELXTL (Bruker, 1998)'
_computing_structure_solution    'SHELXTL (Bruker, 1998)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean '0.06 mm'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'Kuma KM-4 CCD diffractometer'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10568
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.68
_diffrn_reflns_theta_min         3.06
_diffrn_standards_decay_%        'not applicable'
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_number         'not applicable'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   SHELXTL
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       planar
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3438
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0594P)²+0.1325P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1250
_reflns_number_gt                2477
_reflns_number_total             3438
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702563n-File003.cif
_cod_data_source_block           melsa4
_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               4023362
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
N1 N 0.2822(2) 0.14885(5) 0.18817(14) 0.0236(3) Uani 1 1 d . . .
C1 C 0.2089(3) 0.10728(6) 0.23054(16) 0.0214(3) Uani 1 1 d . . .
C2 C 0.2770(3) 0.06135(6) 0.15513(17) 0.0216(3) Uani 1 1 d . . .
H2A H 0.1464 0.0376 0.1302 0.026 Uiso 1 1 calc R . .
H2B H 0.4090 0.0438 0.2152 0.026 Uiso 1 1 calc R . .
C3 C 0.3440(3) 0.08415(5) 0.01916(16) 0.0190(3) Uani 1 1 d . . .
C4 C 0.4168(3) 0.13878(6) 0.07474(16) 0.0206(3) Uani 1 1 d . . .
H4 H 0.5836 0.1379 0.1212 0.025 Uiso 1 1 calc R . .
C5 C 0.1554(3) 0.08160(6) -0.11601(16) 0.0213(3) Uani 1 1 d . . .
H5A H 0.0533 0.0523 -0.1120 0.026 Uiso 1 1 calc R . .
H5B H 0.0611 0.1126 -0.1269 0.026 Uiso 1 1 calc R . .
C6 C 0.2884(3) 0.07622(6) -0.23986(17) 0.0245(4) Uani 1 1 d . . .
H6A H 0.2071 0.0531 -0.3150 0.029 Uiso 1 1 calc R . .
H6B H 0.3056 0.1093 -0.2851 0.029 Uiso 1 1 calc R . .
O1 O 0.51186(19) 0.05603(4) -0.17520(12) 0.0239(3) Uani 1 1 d . . .
C7 C 0.5456(3) 0.05813(6) -0.02967(17) 0.0204(3) Uani 1 1 d . . .
O2 O 0.71670(19) 0.04174(4) 0.04429(12) 0.0267(3) Uani 1 1 d . . .
C8 C 0.3855(3) 0.17879(6) -0.04067(16) 0.0206(3) Uani 1 1 d . . .
C9 C 0.5484(3) 0.18469(6) -0.12892(18) 0.0254(4) Uani 1 1 d . . .
H9 H 0.6841 0.1647 -0.1124 0.030 Uiso 1 1 calc R . .
C10 C 0.5148(3) 0.21944(6) -0.24077(19) 0.0295(4) Uani 1 1 d . . .
H10 H 0.6265 0.2229 -0.3012 0.035 Uiso 1 1 calc R . .
C11 C 0.3193(3) 0.24909(7) -0.26461(19) 0.0304(4) Uani 1 1 d . . .
H11 H 0.2957 0.2726 -0.3420 0.037 Uiso 1 1 calc R . .
C12 C 0.1585(3) 0.24448(6) -0.17585(19) 0.0290(4) Uani 1 1 d . . .
H12 H 0.0253 0.2653 -0.1908 0.035 Uiso 1 1 calc R . .
C13 C 0.1919(3) 0.20933(6) -0.06461(18) 0.0251(4) Uani 1 1 d . . .
H13 H 0.0804 0.2062 -0.0040 0.030 Uiso 1 1 calc R . .
C14 C 0.0693(3) 0.10580(6) 0.34571(16) 0.0235(3) Uani 1 1 d . . .
C15 C 0.0501(3) 0.14853(7) 0.42831(19) 0.0317(4) Uani 1 1 d . . .
H15 H 0.1356 0.1778 0.4149 0.038 Uiso 1 1 calc R . .
C16 C -0.0922(4) 0.14856(8) 0.5293(2) 0.0401(5) Uani 1 1 d . . .
H16 H -0.1046 0.1779 0.5850 0.048 Uiso 1 1 calc R . .
C17 C -0.2167(3) 0.10615(8) 0.54978(19) 0.0396(5) Uani 1 1 d . . .
H17 H -0.3173 0.1066 0.6179 0.048 Uiso 1 1 calc R . .
C18 C -0.1954(3) 0.06322(8) 0.47158(19) 0.0372(5) Uani 1 1 d . . .
H18 H -0.2790 0.0338 0.4872 0.045 Uiso 1 1 calc R . .
C19 C -0.0518(3) 0.06280(7) 0.36978(18) 0.0304(4) Uani 1 1 d . . .
H19 H -0.0364 0.0330 0.3165 0.036 Uiso 1 1 calc R . .
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
C1 N1 C4 109.13(13) . . ?
N1 C1 C14 121.19(14) . . ?
N1 C1 C2 114.96(13) . . ?
C14 C1 C2 123.85(14) . . ?
C1 C2 C3 101.72(12) . . ?
C7 C3 C5 102.69(12) . . ?
C7 C3 C2 114.12(13) . . ?
C5 C3 C2 114.52(12) . . ?
C7 C3 C4 109.87(12) . . ?
C5 C3 C4 115.34(12) . . ?
C2 C3 C4 100.73(11) . . ?
N1 C4 C8 112.49(12) . . ?
N1 C4 C3 104.95(11) . . ?
C8 C4 C3 115.09(13) . . ?
C6 C5 C3 103.86(12) . . ?
O1 C6 C5 105.78(12) . . ?
C7 O1 C6 111.24(12) . . ?
O2 C7 O1 121.65(14) . . ?
O2 C7 C3 127.93(14) . . ?
O1 C7 C3 110.41(13) . . ?
C13 C8 C9 118.51(14) . . ?
C13 C8 C4 121.27(14) . . ?
C9 C8 C4 120.19(14) . . ?
C10 C9 C8 120.66(15) . . ?
C11 C10 C9 120.13(15) . . ?
C12 C11 C10 119.91(16) . . ?
C11 C12 C13 119.75(15) . . ?
C8 C13 C12 121.02(15) . . ?
C19 C14 C15 118.97(15) . . ?
C19 C14 C1 120.96(15) . . ?
C15 C14 C1 120.02(15) . . ?
C16 C15 C14 120.44(17) . . ?
C15 C16 C17 120.23(18) . . ?
C18 C17 C16 120.08(17) . . ?
C17 C18 C19 120.06(18) . . ?
C14 C19 C18 120.17(17) . . ?
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
N1 C1 1.278(2) . ?
N1 C4 1.4661(19) . ?
C1 C14 1.476(2) . ?
C1 C2 1.504(2) . ?
C2 C3 1.530(2) . ?
C3 C7 1.519(2) . ?
C3 C5 1.527(2) . ?
C3 C4 1.577(2) . ?
C4 C8 1.506(2) . ?
C5 C6 1.525(2) . ?
C6 O1 1.4489(19) . ?
O1 C7 1.3450(19) . ?
C7 O2 1.1968(19) . ?
C8 C13 1.386(2) . ?
C8 C9 1.389(2) . ?
C9 C10 1.386(2) . ?
C10 C11 1.381(2) . ?
C11 C12 1.379(2) . ?
C12 C13 1.389(2) . ?
C14 C19 1.390(2) . ?
C14 C15 1.393(2) . ?
C15 C16 1.378(2) . ?
C16 C17 1.379(3) . ?
C17 C18 1.377(3) . ?
C18 C19 1.390(2) . ?
