#------------------------------------------------------------------------------
#$Date: 2017-04-05 12:09:42 +0300 (Wed, 05 Apr 2017) $
#$Revision: 194938 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/97/7119724.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_7119724
loop_
_publ_author_name
'Wu, Xia'
'Geng, Xiao'
'Zhao, Peng'
'Zhang, Jingjing'
'Wu, Yan-Dong'
'Wu, An-Xin'
_publ_section_title
;
 I2-Promoted formal [3+2] cycloaddition of α-methylenyl isocyanides with
 methyl ketones: a route to 2,5-disubstituted oxazoles.
;
_journal_issue                   24
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3438
_journal_page_last               3441
_journal_paper_doi               10.1039/c6cc10275a
_journal_volume                  53
_journal_year                    2017
_chemical_formula_sum            'C14 H15 N O4'
_chemical_formula_weight         261.27
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-10-24 deposited with the CCDC.
2017-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.388(3)
_cell_length_b                   6.6658(13)
_cell_length_c                   14.112(3)
_cell_measurement_reflns_used    4287
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.06
_cell_measurement_theta_min      2.83
_cell_volume                     1353.4(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  CCD
_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  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14228
_diffrn_reflns_theta_full        32.13
_diffrn_reflns_theta_max         32.13
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9832
_exptl_absorpt_correction_T_min  0.9795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.193
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         2437
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0755
_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)+(0.1349P)²+0.3183P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2062
_refine_ls_wR_factor_ref         0.2460
_reflns_number_gt                1580
_reflns_number_total             2437
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc10275a2.cif
_cod_data_source_block           2
_cod_depositor_comments          'Adding full bibliography for 7119724.cif.'
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               7119724
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
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
O1 O 0.79144(14) 0.7500 0.38498(15) 0.0738(6) Uani 1 2 d S . .
O2 O 0.38732(11) 0.7500 0.56548(11) 0.0465(4) Uani 1 2 d S A .
O3 O 0.21090(14) 0.7500 0.52067(15) 0.0779(7) Uani 1 2 d SU . .
O4 O 0.16479(15) 0.7500 0.67208(17) 0.0822(7) Uani 1 2 d S . .
N1 N 0.35957(16) 0.7500 0.72020(15) 0.0587(6) Uani 1 2 d S A .
C1 C 0.8785(3) 0.7500 0.2417(4) 0.1089(15) Uani 1 2 d S . .
H1A H 0.9142 0.8571 0.2690 0.163 Uiso 0.50 1 calc PR . .
H1B H 0.8744 0.7687 0.1744 0.163 Uiso 0.50 1 calc PR . .
H1C H 0.9083 0.6242 0.2549 0.163 Uiso 0.50 1 calc PR . .
C2 C 0.7833(3) 0.7500 0.2833(2) 0.0772(9) Uani 1 2 d S . .
H2A H 0.7495 0.8680 0.2625 0.093 Uiso 0.50 1 calc PR . .
H2B H 0.7495 0.6320 0.2625 0.093 Uiso 0.50 1 calc PR . .
C3 C 0.71048(18) 0.7500 0.43543(18) 0.0537(6) Uani 1 2 d S . .
C4 C 0.62331(18) 0.7500 0.39504(17) 0.0534(6) Uani 1 2 d S . .
H4 H 0.6165 0.7500 0.3295 0.064 Uiso 1 2 calc SR . .
C5 C 0.54575(17) 0.7500 0.45360(16) 0.0497(5) Uani 1 2 d S . .
H5 H 0.4869 0.7500 0.4264 0.060 Uiso 1 2 calc SR . .
C6 C 0.55373(15) 0.7500 0.55086(15) 0.0433(5) Uani 1 2 d S . .
C7 C 0.64251(16) 0.7500 0.59036(17) 0.0531(6) Uani 1 2 d S . .
H7 H 0.6495 0.7500 0.6559 0.064 Uiso 1 2 calc SR . .
C8 C 0.71946(18) 0.7500 0.5333(2) 0.0594(6) Uani 1 2 d S . .
H8 H 0.7784 0.7500 0.5605 0.071 Uiso 1 2 calc SR . .
C9 C 0.47173(14) 0.7500 0.60963(15) 0.0439(5) Uani 1 2 d S . .
C10 C 0.45398(18) 0.7500 0.70503(17) 0.0553(6) Uani 1 2 d S . .
H10 H 0.4990 0.7500 0.7524 0.066 Uiso 1 2 calc SR . .
C11 C 0.32406(16) 0.7500 0.63625(17) 0.0501(5) Uani 1 2 d S . .
C12 C 0.22490(17) 0.7500 0.6128(2) 0.0584(6) Uani 1 2 d S A .
C13 C 0.1135(3) 0.8038(11) 0.4929(4) 0.100(2) Uani 0.50 1 d PU A -1
H13A H 0.0701 0.7774 0.5440 0.120 Uiso 0.50 1 calc PR A -1
H13B H 0.1089 0.9437 0.4745 0.120 Uiso 0.50 1 calc PR A -1
C14 C 0.0973(5) 0.6731(16) 0.4137(6) 0.190(5) Uani 0.50 1 d PU A -1
H14A H 0.0346 0.6898 0.3917 0.285 Uiso 0.50 1 calc PR A -1
H14B H 0.1067 0.5364 0.4329 0.285 Uiso 0.50 1 calc PR A -1
H14C H 0.1398 0.7056 0.3635 0.285 Uiso 0.50 1 calc PR A -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
_geom_angle_site_symmetry_3
C3 O1 C2 116.8(2) .
C11 O2 C9 105.18(17) .
C12 O3 C13 113.7(3) .
C12 O3 C13 113.7(3) 8_575
C13 O3 C13 27.7(5) 8_575
C11 N1 C10 104.4(2) .
C2 C1 H1A 109.5 .
C2 C1 H1B 109.5 .
H1A C1 H1B 109.5 .
C2 C1 H1C 109.5 .
H1A C1 H1C 109.5 .
H1B C1 H1C 109.5 .
O1 C2 C1 108.5(3) .
O1 C2 H2A 110.0 .
C1 C2 H2A 110.0 .
O1 C2 H2B 110.0 .
C1 C2 H2B 110.0 .
H2A C2 H2B 108.4 .
O1 C3 C4 124.1(2) .
O1 C3 C8 116.1(2) .
C4 C3 C8 119.8(2) .
C3 C4 C5 119.0(2) .
C3 C4 H4 120.5 .
C5 C4 H4 120.5 .
C6 C5 C4 121.7(2) .
C6 C5 H5 119.1 .
C4 C5 H5 119.1 .
C5 C6 C7 118.4(2) .
C5 C6 C9 120.3(2) .
C7 C6 C9 121.32(19) .
C8 C7 C6 120.4(2) .
C8 C7 H7 119.8 .
C6 C7 H7 119.8 .
C7 C8 C3 120.7(2) .
C7 C8 H8 119.7 .
C3 C8 H8 119.7 .
O2 C9 C10 106.42(19) .
O2 C9 C6 117.74(18) .
C10 C9 C6 135.8(2) .
N1 C10 C9 109.7(2) .
N1 C10 H10 125.2 .
C9 C10 H10 125.2 .
N1 C11 O2 114.3(2) .
N1 C11 C12 126.4(2) .
O2 C11 C12 119.3(2) .
O4 C12 O3 125.2(3) .
O4 C12 C11 122.9(3) .
O3 C12 C11 111.9(2) .
C14 C13 O3 102.1(5) .
C14 C13 H13A 111.3 .
O3 C13 H13A 111.3 .
C14 C13 H13B 111.3 .
O3 C13 H13B 111.3 .
H13A C13 H13B 109.2 .
C13 C14 H14A 109.5 .
C13 C14 H14B 109.5 .
H14A C14 H14B 109.5 .
C13 C14 H14C 109.5 .
H14A C14 H14C 109.5 .
H14B C14 H14C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C3 1.365(3) .
O1 C2 1.440(4) .
O2 C11 1.351(3) .
O2 C9 1.365(3) .
O3 C12 1.315(3) .
O3 C13 1.499(5) .
O3 C13 1.499(5) 8_575
O4 C12 1.203(3) .
N1 C11 1.290(3) .
N1 C10 1.375(3) .
C1 C2 1.490(5) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.378(4) .
C3 C8 1.388(4) .
C4 C5 1.389(3) .
C4 H4 0.9300 .
C5 C6 1.377(3) .
C5 H5 0.9300 .
C6 C7 1.394(3) .
C6 C9 1.442(3) .
C7 C8 1.369(3) .
C7 H7 0.9300 .
C8 H8 0.9300 .
C9 C10 1.370(3) .
C10 H10 0.9300 .
C11 C12 1.465(4) .
C13 C14 1.436(9) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
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
_geom_torsion_site_symmetry_1
C3 O1 C2 C1 180.0 .
C2 O1 C3 C4 0.000(1) .
C2 O1 C3 C8 180.0 .
O1 C3 C4 C5 180.0 .
C8 C3 C4 C5 0.000(1) .
C3 C4 C5 C6 0.000(1) .
C4 C5 C6 C7 0.0 .
C4 C5 C6 C9 180.0 .
C5 C6 C7 C8 0.0 .
C9 C6 C7 C8 180.0 .
C6 C7 C8 C3 0.0 .
O1 C3 C8 C7 180.0 .
C4 C3 C8 C7 0.0 .
C11 O2 C9 C10 0.0 .
C11 O2 C9 C6 180.0 .
C5 C6 C9 O2 0.000(1) .
C7 C6 C9 O2 180.0 .
C5 C6 C9 C10 180.0 .
C7 C6 C9 C10 0.000(1) .
C11 N1 C10 C9 0.0 .
O2 C9 C10 N1 0.0 .
C6 C9 C10 N1 180.0 .
C10 N1 C11 O2 0.0 .
C10 N1 C11 C12 180.0 .
C9 O2 C11 N1 0.000(1) .
C9 O2 C11 C12 180.0 .
C13 O3 C12 O4 15.2(3) .
C13 O3 C12 O4 -15.2(3) 8_575
C13 O3 C12 C11 -164.8(3) .
C13 O3 C12 C11 164.8(3) 8_575
N1 C11 C12 O4 0.0 .
O2 C11 C12 O4 180.0 .
N1 C11 C12 O3 180.0 .
O2 C11 C12 O3 0.0 .
C12 O3 C13 C14 -142.4(5) .
C13 O3 C13 C14 -46.2(6) 8_575
