#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:38:22 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180309 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/23/7152370.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_7152370
loop_
_publ_author_name
'Harding, Sarah L.'
'Savage, G. Paul'
_publ_section_title
;
 Facial selectivity induced by N-aryl atropisomerism in benzonitrile oxide
 cycloadditions with 4-methylene-2-oxazolidinones.
;
_journal_issue                   24
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4759
_journal_page_last               4766
_journal_paper_doi               10.1039/c2ob25271f
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C14 H17 N O2'
_chemical_formula_sum            'C14 H17 N O2'
_chemical_formula_weight         231.29
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.647(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9538(3)
_cell_length_b                   14.0904(4)
_cell_length_c                   9.3597(3)
_cell_measurement_reflns_used    5904
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      32.1124
_cell_measurement_theta_min      2.1205
_cell_volume                     1264.08(7)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug 2 2010,13:00:58)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug 2 2010,13:00:58)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug 2 2010,13:00:58)
;
_computing_molecular_graphics    X-SEED
_computing_publication_material  CIFTAB
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.3389
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15445
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         32.19
_diffrn_reflns_theta_min         2.12
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug 2 2010,13:00:58)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         4197
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0447
_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)+(0.0580P)²+0.3390P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1280
_reflns_number_gt                3371
_reflns_number_total             4197
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25271f.txt
_cod_data_source_block           mx114_11
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7152370
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
_atom_site_refinement_flags
O1 O 0.45235(7) 0.01265(5) 0.23570(8) 0.02214(17) Uani 1 1 d .
O2 O 0.62525(9) -0.07531(6) 0.38093(10) 0.0295(2) Uani 1 1 d .
N1 N 0.64553(8) 0.08706(6) 0.35813(9) 0.01752(17) Uani 1 1 d .
C1 C 0.58016(10) 0.00071(7) 0.33116(11) 0.01892(19) Uani 1 1 d .
C2 C 0.42739(10) 0.11342(7) 0.19558(11) 0.01966(19) Uani 1 1 d .
C3 C 0.55993(10) 0.16111(7) 0.28521(11) 0.01896(19) Uani 1 1 d .
C4 C 0.78235(10) 0.10037(7) 0.45621(10) 0.01660(18) Uani 1 1 d .
C5 C 0.89455(10) 0.11646(7) 0.39656(11) 0.01912(19) Uani 1 1 d .
C6 C 1.02510(11) 0.12849(8) 0.49768(12) 0.0235(2) Uani 1 1 d .
H6 H 1.1044 0.1387 0.4616 0.028 Uiso 1 1 calc R
C7 C 1.04166(11) 0.12592(8) 0.64935(12) 0.0240(2) Uani 1 1 d .
H7 H 1.1320 0.1344 0.7150 0.029 Uiso 1 1 calc R
C8 C 0.92839(11) 0.11121(7) 0.70751(11) 0.0210(2) Uani 1 1 d .
C9 C 0.79771(10) 0.09795(7) 0.60818(11) 0.01898(19) Uani 1 1 d .
H9 H 0.7186 0.0872 0.6445 0.023 Uiso 1 1 calc R
C10 C 0.87688(12) 0.11890(9) 0.23211(12) 0.0261(2) Uani 1 1 d .
H10A H 0.8278 0.0616 0.1866 0.039 Uiso 1 1 calc R
H10B H 0.9688 0.1217 0.2127 0.039 Uiso 1 1 calc R
H10C H 0.8226 0.1750 0.1897 0.039 Uiso 1 1 calc R
C11 C 0.94594(13) 0.11007(9) 0.87263(12) 0.0298(2) Uani 1 1 d .
H11A H 0.9519 0.1754 0.9098 0.045 Uiso 1 1 calc R
H11B H 1.0316 0.0758 0.9219 0.045 Uiso 1 1 calc R
H11C H 0.8657 0.0783 0.8935 0.045 Uiso 1 1 calc R
C12 C 0.59027(12) 0.25247(8) 0.29469(14) 0.0287(2) Uani 1 1 d .
H12A H 0.6777 0.2735 0.3557 0.034 Uiso 1 1 calc R
H12B H 0.5247 0.2972 0.2405 0.034 Uiso 1 1 calc R
C13 C 0.29973(11) 0.14440(10) 0.24241(14) 0.0302(2) Uani 1 1 d .
H13A H 0.2171 0.1119 0.1812 0.045 Uiso 1 1 calc R
H13B H 0.2876 0.2132 0.2293 0.045 Uiso 1 1 calc R
H13C H 0.3120 0.1282 0.3470 0.045 Uiso 1 1 calc R
C14 C 0.40795(14) 0.12157(10) 0.02952(13) 0.0326(3) Uani 1 1 d .
H14A H 0.3210 0.0900 -0.0233 0.049 Uiso 1 1 calc R
H14B H 0.4867 0.0913 0.0033 0.049 Uiso 1 1 calc R
H14C H 0.4035 0.1887 0.0013 0.049 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
C1 O1 C2 110.61(7)
C1 N1 C3 112.01(8)
C1 N1 C4 123.74(8)
C3 N1 C4 124.16(8)
O2 C1 O1 123.45(9)
O2 C1 N1 127.51(9)
O1 C1 N1 109.04(8)
O1 C2 C13 107.51(9)
O1 C2 C3 102.98(7)
C13 C2 C3 112.61(9)
O1 C2 C14 107.47(9)
C13 C2 C14 112.89(9)
C3 C2 C14 112.62(9)
C12 C3 N1 126.51(10)
C12 C3 C2 128.22(9)
N1 C3 C2 105.27(8)
C9 C4 C5 122.32(9)
C9 C4 N1 118.37(8)
C5 C4 N1 119.30(8)
C4 C5 C6 116.59(9)
C4 C5 C10 121.92(9)
C6 C5 C10 121.48(9)
C7 C6 C5 121.56(9)
C6 C7 C8 121.28(9)
C9 C8 C7 117.89(9)
C9 C8 C11 120.80(10)
C7 C8 C11 121.31(10)
C4 C9 C8 120.35(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3535(12)
O1 C2 1.4726(12)
O2 C1 1.2054(12)
N1 C1 1.3707(12)
N1 C3 1.4024(12)
N1 C4 1.4346(12)
C2 C13 1.5160(15)
C2 C3 1.5162(14)
C2 C14 1.5180(14)
C3 C12 1.3198(15)
C4 C9 1.3894(13)
C4 C5 1.3952(13)
C5 C6 1.3963(14)
C5 C10 1.5018(14)
C6 C7 1.3847(16)
C7 C8 1.3934(15)
C8 C9 1.3924(14)
C8 C11 1.5079(15)
