#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/36/1503647.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_1503647
loop_
_publ_author_name
'Tu, Shu-Jiang'
'Zhang, Xiao-Hong'
'Han, Zheng-Guo'
'Cao, Xu-Dong'
'Wu, Shan-Shan'
'Yan, Shu'
'Hao, Wen-Juan'
'Zhang, Ge'
'Ma, Ning'
_publ_section_title
;
 Synthesis of Isoxazolo[5,4-b]pyridines by Microwave-Assisted
 Multi-Component Reactions in Water
;
_journal_issue                   3
_journal_name_full               'Journal of Combinatorial Chemistry'
_journal_page_first              428
_journal_paper_doi               10.1021/cc800212v
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C16 H12 N2 O4'
_chemical_formula_weight         296.28
_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                 95.5920(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8513(16)
_cell_length_b                   7.6116(11)
_cell_length_c                   12.6732(15)
_cell_measurement_reflns_used    1263
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.513
_cell_measurement_theta_min      2.956
_cell_volume                     1329.8(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0853
_diffrn_reflns_av_sigmaI/netI    0.0841
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6625
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_correction_T_min  0.9850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2333
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1284
_refine_ls_R_factor_gt           0.0575
_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)+(0.0242P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0934
_reflns_number_gt                1267
_reflns_number_total             2333
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cc800212v_si_003.cif
_cod_data_source_block           080820a
_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 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1503647
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
N1 N 0.19564(17) -0.0001(3) 0.93775(17) 0.0496(6) Uani 1 1 d .
N2 N 0.42384(17) -0.1679(3) 0.8929(2) 0.0646(7) Uani 1 1 d .
O1 O -0.00728(12) 0.1886(3) 0.77882(13) 0.0530(5) Uani 1 1 d .
O2 O 0.03096(12) 0.1945(3) 0.61265(14) 0.0561(5) Uani 1 1 d .
O3 O 0.35098(14) -0.1183(3) 0.95948(14) 0.0625(6) Uani 1 1 d .
O4 O 0.30666(13) 0.0742(2) 0.28784(14) 0.0553(6) Uani 1 1 d .
C1 C 0.1314(2) 0.0595(3) 0.8621(2) 0.0413(7) Uani 1 1 d .
C2 C 0.03488(19) 0.1313(4) 0.8820(2) 0.0545(8) Uani 1 1 d .
H2A H -0.0049 0.0415 0.9106 0.065 Uiso 1 1 calc R
H2B H 0.0418 0.2291 0.9312 0.065 Uiso 1 1 calc R
C3 C 0.05378(18) 0.1546(4) 0.7033(2) 0.0431(7) Uani 1 1 d .
C4 C 0.14180(18) 0.0708(3) 0.75423(18) 0.0371(6) Uani 1 1 d .
C5 C 0.22780(17) 0.0190(3) 0.71290(19) 0.0364(6) Uani 1 1 d .
C6 C 0.29723(19) -0.0463(3) 0.7918(2) 0.0411(7) Uani 1 1 d .
C7 C 0.2760(2) -0.0493(4) 0.8971(2) 0.0461(7) Uani 1 1 d .
C8 C 0.3921(2) -0.1270(4) 0.7960(2) 0.0496(7) Uani 1 1 d .
C9 C 0.45235(19) -0.1739(4) 0.7089(2) 0.0653(9) Uani 1 1 d .
H9A H 0.4837 -0.0703 0.6857 0.098 Uiso 1 1 calc R
H9B H 0.4117 -0.2232 0.6507 0.098 Uiso 1 1 calc R
H9C H 0.5006 -0.2584 0.7344 0.098 Uiso 1 1 calc R
C10 C 0.24536(17) 0.0332(3) 0.60100(18) 0.0366(6) Uani 1 1 d .
C11 C 0.18199(17) -0.0388(3) 0.52099(19) 0.0410(7) Uani 1 1 d .
H11 H 0.1263 -0.0955 0.5385 0.049 Uiso 1 1 calc R
C12 C 0.19987(17) -0.0281(3) 0.41641(19) 0.0424(7) Uani 1 1 d .
H12 H 0.1567 -0.0784 0.3642 0.051 Uiso 1 1 calc R
C13 C 0.28166(18) 0.0570(4) 0.3886(2) 0.0411(7) Uani 1 1 d .
C14 C 0.34544(18) 0.1327(3) 0.4676(2) 0.0438(7) Uani 1 1 d .
H14 H 0.4002 0.1921 0.4498 0.053 Uiso 1 1 calc R
C15 C 0.32724(17) 0.1194(3) 0.5715(2) 0.0420(7) Uani 1 1 d .
H15 H 0.3706 0.1691 0.6237 0.050 Uiso 1 1 calc R
C16 C 0.2431(2) 0.0018(4) 0.2031(2) 0.0576(8) Uani 1 1 d .
H16A H 0.2355 -0.1219 0.2145 0.086 Uiso 1 1 calc R
H16B H 0.2703 0.0203 0.1371 0.086 Uiso 1 1 calc R
H16C H 0.1810 0.0584 0.2008 0.086 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 N1 C7 110.3(2)
C8 N2 O3 107.5(2)
C3 O1 C2 110.7(2)
C7 O3 N2 107.8(2)
C13 O4 C16 118.2(2)
N1 C1 C4 127.3(3)
N1 C1 C2 123.7(2)
C4 C1 C2 109.0(2)
O1 C2 C1 104.4(2)
O1 C2 H2A 110.9
C1 C2 H2A 110.9
O1 C2 H2B 110.9
C1 C2 H2B 110.9
H2A C2 H2B 108.9
O2 C3 O1 120.0(2)
O2 C3 C4 131.4(2)
O1 C3 C4 108.6(2)
C1 C4 C5 121.5(2)
C1 C4 C3 107.3(2)
C5 C4 C3 131.0(2)
C4 C5 C6 112.3(2)
C4 C5 C10 124.6(2)
C6 C5 C10 123.1(2)
C7 C6 C5 119.5(3)
C7 C6 C8 103.5(2)
C5 C6 C8 136.9(3)
N1 C7 O3 120.7(3)
N1 C7 C6 129.1(3)
O3 C7 C6 110.2(3)
N2 C8 C6 111.0(2)
N2 C8 C9 118.6(3)
C6 C8 C9 130.3(3)
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C11 C10 C15 117.6(2)
C11 C10 C5 121.7(2)
C15 C10 C5 120.7(2)
C12 C11 C10 121.4(2)
C12 C11 H11 119.3
C10 C11 H11 119.3
C11 C12 C13 120.2(2)
C11 C12 H12 119.9
C13 C12 H12 119.9
O4 C13 C12 125.1(2)
O4 C13 C14 115.6(2)
C12 C13 C14 119.3(2)
C15 C14 C13 119.8(2)
C15 C14 H14 120.1
C13 C14 H14 120.1
C14 C15 C10 121.7(2)
C14 C15 H15 119.2
C10 C15 H15 119.2
O4 C16 H16A 109.5
O4 C16 H16B 109.5
H16A C16 H16B 109.5
O4 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.324(3)
N1 C7 1.325(3)
N2 C8 1.302(3)
N2 O3 1.428(3)
O1 C3 1.363(3)
O1 C2 1.446(3)
O2 C3 1.200(3)
O3 C7 1.349(3)
O4 C13 1.361(3)
O4 C16 1.431(3)
C1 C4 1.391(3)
C1 C2 1.488(3)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.469(3)
C4 C5 1.404(3)
C5 C6 1.409(3)
C5 C10 1.466(3)
C6 C7 1.395(3)
C6 C8 1.446(3)
C8 C9 1.490(4)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 C11 1.388(3)
C10 C15 1.393(3)
C11 C12 1.374(3)
C11 H11 0.9300
C12 C13 1.380(3)
C12 H12 0.9300
C13 C14 1.394(3)
C14 C15 1.368(3)
C14 H14 0.9300
C15 H15 0.9300
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 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
C8 N2 O3 C7 0.6(3)
C7 N1 C1 C4 0.6(4)
C7 N1 C1 C2 -177.6(2)
C3 O1 C2 C1 1.0(3)
N1 C1 C2 O1 176.8(2)
C4 C1 C2 O1 -1.6(3)
C2 O1 C3 O2 -179.5(2)
C2 O1 C3 C4 0.0(3)
N1 C1 C4 C5 -1.1(4)
C2 C1 C4 C5 177.3(2)
N1 C1 C4 C3 -176.8(3)
C2 C1 C4 C3 1.7(3)
O2 C3 C4 C1 178.3(3)
O1 C3 C4 C1 -1.1(3)
O2 C3 C4 C5 3.2(5)
O1 C3 C4 C5 -176.1(2)
C1 C4 C5 C6 1.4(3)
C3 C4 C5 C6 175.9(3)
C1 C4 C5 C10 -177.6(2)
C3 C4 C5 C10 -3.1(4)
C4 C5 C6 C7 -1.4(3)
C10 C5 C6 C7 177.7(2)
C4 C5 C6 C8 174.6(3)
C10 C5 C6 C8 -6.4(5)
C1 N1 C7 O3 -178.5(2)
C1 N1 C7 C6 -0.6(4)
N2 O3 C7 N1 176.5(2)
N2 O3 C7 C6 -1.7(3)
C5 C6 C7 N1 1.1(4)
C8 C6 C7 N1 -176.1(3)
C5 C6 C7 O3 179.2(2)
C8 C6 C7 O3 2.0(3)
O3 N2 C8 C6 0.7(3)
O3 N2 C8 C9 -176.8(2)
C7 C6 C8 N2 -1.7(3)
C5 C6 C8 N2 -178.1(3)
C7 C6 C8 C9 175.4(3)
C5 C6 C8 C9 -1.0(5)
C4 C5 C10 C11 -53.8(4)
C6 C5 C10 C11 127.3(3)
C4 C5 C10 C15 126.5(3)
C6 C5 C10 C15 -52.4(4)
C15 C10 C11 C12 1.0(4)
C5 C10 C11 C12 -178.7(2)
C10 C11 C12 C13 -0.7(4)
C16 O4 C13 C12 1.1(4)
C16 O4 C13 C14 -179.0(2)
C11 C12 C13 O4 179.5(2)
C11 C12 C13 C14 -0.4(4)
O4 C13 C14 C15 -178.8(2)
C12 C13 C14 C15 1.1(4)
C13 C14 C15 C10 -0.8(4)
C11 C10 C15 C14 -0.3(4)
C5 C10 C15 C14 179.4(2)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 24742155 ChemSpider
