#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/45/4024505.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_4024505
loop_
_publ_author_name
'Ke-Lai Li'
'Zong-Bo Du'
'Can-Cheng Guo'
'Qing-Yun Chen'
_publ_section_title
;
Regioselective Syntheses of 2- and 4-Formylpyrido[2,1-b]benzoxazoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3286
_journal_page_last               3292
_journal_paper_doi               10.1021/jo900267c
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C12 H7 N O3'
_chemical_formula_weight         213.19
_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                 96.046(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0473(15)
_cell_length_b                   7.9725(13)
_cell_length_c                   13.064(2)
_cell_measurement_reflns_used    1431
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      48.740
_cell_measurement_theta_min      4.527
_cell_volume                     937.0(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      292(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  0.1338
_diffrn_reflns_av_sigmaI/netI    0.0964
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5368
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60427
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.471
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.128
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2050
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0496
_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)+(0.0424P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1243
_reflns_number_gt                1428
_reflns_number_total             2050
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900267c_si_002.cif
_cod_data_source_block           cd26277
_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      P2(1)/c
_cod_database_code               4024505
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.52716(13) 0.52724(16) 0.23170(11) 0.0504(4) Uani 1 1 d . . .
O2 O 0.58402(12) 0.17873(14) 0.50315(10) 0.0422(3) Uani 1 1 d . . .
O3 O 0.94240(15) 0.4304(2) 0.14394(13) 0.0667(5) Uani 1 1 d . . .
N1 N 0.56998(14) 0.34858(15) 0.36746(11) 0.0332(4) Uani 1 1 d . . .
C1 C 0.61399(18) 0.4303(2) 0.27950(14) 0.0370(4) Uani 1 1 d . . .
C2 C 0.76146(17) 0.3857(2) 0.25932(14) 0.0377(4) Uani 1 1 d . . .
C3 C 0.84487(18) 0.2704(2) 0.32070(16) 0.0406(5) Uani 1 1 d . . .
C4 C 0.79645(19) 0.1937(2) 0.40488(16) 0.0428(5) Uani 1 1 d . . .
C5 C 0.65662(17) 0.2376(2) 0.42565(14) 0.0358(4) Uani 1 1 d . . .
C6 C 0.43290(17) 0.35901(19) 0.40909(14) 0.0350(4) Uani 1 1 d . . .
C7 C 0.44429(17) 0.25335(19) 0.49275(15) 0.0363(4) Uani 1 1 d . . .
C8 C 0.3324(2) 0.2284(2) 0.55462(16) 0.0445(5) Uani 1 1 d . . .
C9 C 0.2023(2) 0.3150(2) 0.52607(17) 0.0503(5) Uani 1 1 d . . .
C10 C 0.1888(2) 0.4223(2) 0.44236(18) 0.0491(5) Uani 1 1 d . . .
C11 C 0.30265(19) 0.4472(2) 0.38066(17) 0.0431(5) Uani 1 1 d . . .
C12 C 0.8221(2) 0.4638(2) 0.17274(17) 0.0497(5) Uani 1 1 d . . .
H12 H 0.7649 0.5454 0.1364 0.060 Uiso 1 1 calc R . .
H3 H 0.9421(19) 0.245(2) 0.3025(14) 0.043(5) Uiso 1 1 d . . .
H4 H 0.855(2) 0.116(2) 0.4475(15) 0.048(5) Uiso 1 1 d . . .
H8 H 0.3400(19) 0.154(2) 0.6115(14) 0.046(5) Uiso 1 1 d . . .
H9 H 0.119(2) 0.304(2) 0.5698(16) 0.050(5) Uiso 1 1 d . . .
H10 H 0.099(2) 0.482(2) 0.4240(15) 0.047(5) Uiso 1 1 d . . .
H11 H 0.2983(19) 0.520(2) 0.3211(15) 0.044(5) Uiso 1 1 d . . .
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
C5 O2 C7 106.70(13) . . ?
C5 N1 C6 107.57(14) . . ?
C5 N1 C1 123.98(14) . . ?
C6 N1 C1 128.41(13) . . ?
O1 C1 N1 118.98(15) . . ?
O1 C1 C2 128.53(18) . . ?
N1 C1 C2 112.49(15) . . ?
C3 C2 C1 121.22(17) . . ?
C3 C2 C12 120.51(16) . . ?
C1 C2 C12 118.27(17) . . ?
C4 C3 C2 123.95(16) . . ?
C4 C3 H3 118.9(11) . . ?
C2 C3 H3 117.2(11) . . ?
C5 C4 C3 115.20(17) . . ?
C5 C4 H4 121.3(11) . . ?
C3 C4 H4 123.5(11) . . ?
O2 C5 N1 110.41(13) . . ?
O2 C5 C4 126.45(16) . . ?
N1 C5 C4 123.14(17) . . ?
C7 C6 C11 120.88(16) . . ?
C7 C6 N1 105.99(14) . . ?
C11 C6 N1 133.13(17) . . ?
C8 C7 C6 123.90(16) . . ?
C8 C7 O2 126.77(17) . . ?
C6 C7 O2 109.33(14) . . ?
C7 C8 C9 115.35(19) . . ?
C7 C8 H8 123.7(11) . . ?
C9 C8 H8 120.9(11) . . ?
C8 C9 C10 121.59(18) . . ?
C8 C9 H9 118.4(11) . . ?
C10 C9 H9 119.9(11) . . ?
C9 C10 C11 122.60(19) . . ?
C9 C10 H10 120.8(11) . . ?
C11 C10 H10 116.6(11) . . ?
C10 C11 C6 115.66(19) . . ?
C10 C11 H11 125.7(10) . . ?
C6 C11 H11 118.6(11) . . ?
O3 C12 C2 124.85(19) . . ?
O3 C12 H12 117.6 . . ?
C2 C12 H12 117.6 . . ?
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
O1 C1 1.225(2) . ?
O2 C5 1.348(2) . ?
O2 C7 1.3909(18) . ?
O3 C12 1.218(2) . ?
N1 C5 1.360(2) . ?
N1 C6 1.408(2) . ?
N1 C1 1.414(2) . ?
C1 C2 1.432(2) . ?
C2 C3 1.389(3) . ?
C2 C12 1.449(3) . ?
C3 C4 1.370(3) . ?
C3 H3 0.958(16) . ?
C4 C5 1.367(2) . ?
C4 H4 0.955(19) . ?
C6 C7 1.375(2) . ?
C6 C11 1.389(2) . ?
C7 C8 1.375(2) . ?
C8 C9 1.382(3) . ?
C8 H8 0.947(18) . ?
C9 C10 1.384(3) . ?
C9 H9 0.995(18) . ?
C10 C11 1.387(3) . ?
C10 H10 0.949(19) . ?
C11 H11 0.967(19) . ?
C12 H12 0.9300 . ?
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 O1 179.38(15) . . . . ?
C6 N1 C1 O1 1.9(2) . . . . ?
C5 N1 C1 C2 -1.0(2) . . . . ?
C6 N1 C1 C2 -178.57(14) . . . . ?
O1 C1 C2 C3 -178.88(16) . . . . ?
N1 C1 C2 C3 1.6(2) . . . . ?
O1 C1 C2 C12 1.0(3) . . . . ?
N1 C1 C2 C12 -178.48(14) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C12 C2 C3 C4 178.75(17) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C7 O2 C5 N1 1.01(18) . . . . ?
C7 O2 C5 C4 -178.11(17) . . . . ?
C6 N1 C5 O2 -1.09(18) . . . . ?
C1 N1 C5 O2 -179.05(14) . . . . ?
C6 N1 C5 C4 178.07(16) . . . . ?
C1 N1 C5 C4 0.1(3) . . . . ?
C3 C4 C5 O2 179.36(16) . . . . ?
C3 C4 C5 N1 0.3(3) . . . . ?
C5 N1 C6 C7 0.72(17) . . . . ?
C1 N1 C6 C7 178.56(15) . . . . ?
C5 N1 C6 C11 -178.10(18) . . . . ?
C1 N1 C6 C11 -0.2(3) . . . . ?
C11 C6 C7 C8 -1.0(3) . . . . ?
N1 C6 C7 C8 179.98(16) . . . . ?
C11 C6 C7 O2 178.88(14) . . . . ?
N1 C6 C7 O2 -0.11(18) . . . . ?
C5 O2 C7 C8 179.37(17) . . . . ?
C5 O2 C7 C6 -0.54(18) . . . . ?
C6 C7 C8 C9 1.5(3) . . . . ?
O2 C7 C8 C9 -178.44(16) . . . . ?
C7 C8 C9 C10 -1.6(3) . . . . ?
C8 C9 C10 C11 1.5(3) . . . . ?
C9 C10 C11 C6 -0.9(3) . . . . ?
C7 C6 C11 C10 0.7(3) . . . . ?
N1 C6 C11 C10 179.34(17) . . . . ?
C3 C2 C12 O3 4.0(3) . . . . ?
C1 C2 C12 O3 -175.87(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658934
