#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:45:47 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180314 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/28/7152839.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_7152839
loop_
_publ_author_name
'Zhang, Jinzhu'
'Wu, Jing'
'Yin, Zhiwei'
'Zeng, Haisu'
'Khanna, Kunal'
'Hu, Chunhua'
'Zheng, Shengping'
_publ_section_title
;
 An expedient stereoselective and chemoselective synthesis of bicyclic
 oxazolidinones from quinols and isocyanates.
;
_journal_issue                   18
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2939
_journal_page_last               2942
_journal_paper_doi               10.1039/c3ob00047h
_journal_volume                  11
_journal_year                    2013
_chemical_formula_sum            'C15 H15 N O4'
_chemical_formula_weight         273.28
_chemical_name_systematic
;
?
;
_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                 96.0380(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1123(4)
_cell_length_b                   17.9740(12)
_cell_length_c                   11.7487(8)
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      3.49
_cell_volume                     1283.58(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26919
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9887
_exptl_absorpt_correction_T_min  0.9463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SABADS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3196
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0424
_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)+(0.0590P)²+0.6366P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1176
_reflns_number_gt                2786
_reflns_number_total             3196
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob00047h.txt
_cod_data_source_block           12spz1h
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7152839
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
O1 O 0.37589(15) 0.09469(5) 0.39494(8) 0.0231(2) Uani 1 1 d .
O2 O 0.22212(15) 0.05264(6) 0.54730(8) 0.0250(2) Uani 1 1 d .
O3 O 0.69723(18) 0.23189(6) 0.26892(9) 0.0313(2) Uani 1 1 d .
O4 O 0.75106(19) 0.32086(6) 0.57580(9) 0.0332(3) Uani 1 1 d .
N1 N 0.56552(16) 0.10921(6) 0.56627(9) 0.0177(2) Uani 1 1 d .
C1 C 0.3746(2) 0.08271(7) 0.50862(11) 0.0188(2) Uani 1 1 d .
C2 C 0.72733(19) 0.12741(7) 0.48633(10) 0.0178(2) Uani 1 1 d .
H2 H 0.8336 0.0854 0.4831 0.021 Uiso 1 1 calc R
C3 C 0.5764(2) 0.13228(7) 0.37207(10) 0.0197(3) Uani 1 1 d .
C4 C 0.5191(2) 0.21159(7) 0.33288(11) 0.0241(3) Uani 1 1 d .
H4 H 0.3779 0.2116 0.2814 0.029 Uiso 1 1 calc R
C5 C 0.7708(3) 0.16594(9) 0.21369(14) 0.0353(3) Uani 1 1 d .
H5A H 0.9333 0.1626 0.2247 0.042 Uiso 1 1 calc R
H5B H 0.7231 0.1675 0.1305 0.042 Uiso 1 1 calc R
C6 C 0.6692(3) 0.09954(8) 0.26807(12) 0.0290(3) Uani 1 1 d .
H6A H 0.7816 0.0612 0.2909 0.035 Uiso 1 1 calc R
H6B H 0.5512 0.0770 0.2148 0.035 Uiso 1 1 calc R
C7 C 0.5056(2) 0.26704(8) 0.42825(12) 0.0267(3) Uani 1 1 d .
H7A H 0.3752 0.2554 0.4684 0.032 Uiso 1 1 calc R
H7B H 0.4845 0.3174 0.3947 0.032 Uiso 1 1 calc R
C8 C 0.7071(2) 0.26755(7) 0.51428(11) 0.0228(3) Uani 1 1 d .
C9 C 0.8519(2) 0.19922(7) 0.51907(11) 0.0219(3) Uani 1 1 d .
H9A H 0.9264 0.1940 0.5976 0.026 Uiso 1 1 calc R
H9B H 0.9670 0.2064 0.4668 0.026 Uiso 1 1 calc R
C10 C 0.6233(2) 0.09119(7) 0.68417(10) 0.0174(2) Uani 1 1 d .
C11 C 0.4763(2) 0.10772(7) 0.76323(11) 0.0224(3) Uani 1 1 d .
H11 H 0.3437 0.1337 0.7399 0.027 Uiso 1 1 calc R
C12 C 0.5248(2) 0.08596(8) 0.87664(11) 0.0260(3) Uani 1 1 d .
H12 H 0.4238 0.0963 0.9308 0.031 Uiso 1 1 calc R
C13 C 0.7197(3) 0.04923(8) 0.91103(11) 0.0278(3) Uani 1 1 d .
H13 H 0.7513 0.0337 0.9883 0.033 Uiso 1 1 calc R
C14 C 0.8682(2) 0.03512(8) 0.83264(12) 0.0274(3) Uani 1 1 d .
H14 H 1.0034 0.0110 0.8570 0.033 Uiso 1 1 calc R
C15 C 0.8219(2) 0.05590(7) 0.71854(11) 0.0218(3) Uani 1 1 d .
H15 H 0.9244 0.0461 0.6649 0.026 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 C3 110.48(9)
C4 O3 C5 108.40(10)
C1 N1 C10 120.68(10)
C1 N1 C2 110.87(10)
C10 N1 C2 123.69(10)
O2 C1 O1 121.84(11)
O2 C1 N1 128.34(12)
O1 C1 N1 109.82(10)
N1 C2 C9 112.21(10)
N1 C2 C3 100.77(9)
C9 C2 C3 113.97(10)
N1 C2 H2 109.9
C9 C2 H2 109.9
C3 C2 H2 109.9
O1 C3 C6 111.29(11)
O1 C3 C4 108.62(10)
C6 C3 C4 102.26(10)
O1 C3 C2 104.54(9)
C6 C3 C2 115.89(11)
C4 C3 C2 114.25(10)
O3 C4 C7 108.97(11)
O3 C4 C3 103.47(11)
C7 C4 C3 114.93(11)
O3 C4 H4 109.7
C7 C4 H4 109.7
C3 C4 H4 109.7
O3 C5 C6 107.20(11)
O3 C5 H5A 110.3
C6 C5 H5A 110.3
O3 C5 H5B 110.3
C6 C5 H5B 110.3
H5A C5 H5B 108.5
C5 C6 C3 103.77(11)
C5 C6 H6A 111.0
C3 C6 H6A 111.0
C5 C6 H6B 111.0
C3 C6 H6B 111.0
H6A C6 H6B 109.0
C4 C7 C8 113.39(11)
C4 C7 H7A 108.9
C8 C7 H7A 108.9
C4 C7 H7B 108.9
C8 C7 H7B 108.9
H7A C7 H7B 107.7
O4 C8 C7 121.19(13)
O4 C8 C9 121.84(12)
C7 C8 C9 116.97(11)
C8 C9 C2 113.77(10)
C8 C9 H9A 108.8
C2 C9 H9A 108.8
C8 C9 H9B 108.8
C2 C9 H9B 108.8
H9A C9 H9B 107.7
C11 C10 C15 120.60(11)
C11 C10 N1 119.16(11)
C15 C10 N1 120.23(11)
C12 C11 C10 119.49(12)
C12 C11 H11 120.3
C10 C11 H11 120.3
C13 C12 C11 120.26(12)
C13 C12 H12 119.9
C11 C12 H12 119.9
C14 C13 C12 119.88(12)
C14 C13 H13 120.1
C12 C13 H13 120.1
C13 C14 C15 120.73(12)
C13 C14 H14 119.6
C15 C14 H14 119.6
C10 C15 C14 118.99(12)
C10 C15 H15 120.5
C14 C15 H15 120.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3537(15)
O1 C3 1.4492(15)
O2 C1 1.2069(15)
O3 C4 1.4336(17)
O3 C5 1.446(2)
O4 C8 1.2132(16)
N1 C1 1.3715(15)
N1 C10 1.4302(15)
N1 C2 1.4706(15)
C2 C9 1.5271(17)
C2 C3 1.5492(17)
C2 H2 1.0000
C3 C6 1.5187(18)
C3 C4 1.5274(18)
C4 C7 1.5083(19)
C4 H4 1.0000
C5 C6 1.517(2)
C5 H5A 0.9900
C5 H5B 0.9900
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.5090(18)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.5114(19)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.3908(17)
C10 C15 1.3915(17)
C11 C12 1.3905(19)
C11 H11 0.9500
C12 C13 1.385(2)
C12 H12 0.9500
C13 C14 1.383(2)
C13 H13 0.9500
C14 C15 1.3917(18)
C14 H14 0.9500
C15 H15 0.9500
