#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/12/7151210.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_7151210
loop_
_publ_author_name
'Heaney, Frances'
'Lawless, Elaine'
'Mahon, Mary'
'McArdle, Patrick'
'Cunningham, Desmond'
_publ_section_title
;
 1,3-Dipolar character of 2-vinyl quinazoline 3-oxides; first and
 second generation cycloaddition products.
;
_journal_issue                   12
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2408
_journal_page_last               2416
_journal_paper_doi               10.1039/b602423h
_journal_volume                  4
_journal_year                    2006
_chemical_formula_sum            'C23 H20 N2 O5'
_chemical_formula_weight         404.41
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.275(9)
_cell_angle_beta                 101.461(11)
_cell_angle_gamma                100.074(13)
_cell_formula_units_Z            2
_cell_length_a                   7.5822(15)
_cell_length_b                   10.3689(13)
_cell_length_c                   13.0588(9)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      12
_cell_volume                     989.9(2)
_computing_cell_refinement       'XDS (W.Kabsch, 2000)'
_computing_data_collection       'Marresearch MarControl software'
_computing_data_reduction        'XDS (W.Kabsch, 2000)'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.918
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'Marresearch image plate'
_diffrn_measurement_method       '180 mm image plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_sigmaI/netI    0.0813
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3934
_diffrn_reflns_theta_full        20.86
_diffrn_reflns_theta_max         20.86
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.079(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         1920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0451
_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)+(0.0571P)²+0.2197P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1202
_reflns_number_gt                1684
_reflns_number_total             1920
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b602423h.txt
_cod_data_source_block           fhm1_1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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      P-1
_cod_database_code               7151210
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 -0.4120(3) 0.86255(19) 0.11811(15) 0.0618(6) Uani 1 1 d . . .
O2 O 0.1689(2) 0.80762(17) 0.19941(14) 0.0496(6) Uani 1 1 d . . .
O3 O -0.0462(3) 0.98251(19) 0.34211(15) 0.0610(6) Uani 1 1 d . . .
O4 O 0.2466(2) 0.96247(17) 0.37649(14) 0.0533(6) Uani 1 1 d . . .
O5 O -0.1302(2) 0.95074(17) 0.10197(13) 0.0507(6) Uani 1 1 d . . .
N1 N 0.0231(3) 0.5386(2) 0.27794(17) 0.0447(6) Uani 1 1 d . . .
N3 N -0.1492(3) 0.6546(2) 0.36797(16) 0.0402(6) Uani 1 1 d . . .
C2 C 0.0047(3) 0.6047(2) 0.3584(2) 0.0398(7) Uani 1 1 d . . .
C4 C -0.2378(3) 0.7169(2) 0.29769(19) 0.0372(7) Uani 1 1 d . . .
C5 C -0.1553(3) 0.7624(2) 0.20175(18) 0.0357(6) Uani 1 1 d . . .
C5A C -0.1756(3) 0.6373(2) 0.13580(18) 0.0369(7) Uani 1 1 d . . .
C6 C -0.2734(3) 0.6212(3) 0.03338(19) 0.0438(7) Uani 1 1 d . . .
H6 H -0.3289 0.6890 0.0035 0.057 Uiso 1 1 calc R . .
C7 C -0.2900(4) 0.5077(3) -0.0248(2) 0.0522(8) Uani 1 1 d . . .
H7 H -0.3548 0.4999 -0.0936 0.068 Uiso 1 1 calc R . .
C8 C -0.2114(4) 0.4055(3) 0.0182(2) 0.0544(8) Uani 1 1 d . . .
H8 H -0.2244 0.3280 -0.0209 0.071 Uiso 1 1 calc R . .
C9 C -0.1139(4) 0.4185(3) 0.1188(2) 0.0510(7) Uani 1 1 d . . .
H9 H -0.0599 0.3494 0.1472 0.066 Uiso 1 1 calc R . .
C9A C -0.0935(3) 0.5332(2) 0.18001(19) 0.0400(7) Uani 1 1 d . . .
C10 C 0.0465(3) 0.8284(2) 0.23880(19) 0.0360(7) Uani 1 1 d . . .
C11 C 0.0771(4) 0.9332(2) 0.32578(19) 0.0402(7) Uani 1 1 d . . .
C12 C 0.2840(4) 1.0643(3) 0.4585(2) 0.0696(10) Uani 1 1 d . . .
H12A H 0.2309 1.1381 0.4322 0.097 Uiso 1 1 calc R . .
H12B H 0.4138 1.0911 0.4812 0.097 Uiso 1 1 calc R . .
H12C H 0.2320 1.0310 0.5165 0.097 Uiso 1 1 calc R . .
C13 C -0.2519(4) 0.8629(2) 0.13793(19) 0.0415(7) Uani 1 1 d . . .
C14 C -0.2018(4) 1.0536(3) 0.0413(2) 0.0654(9) Uani 1 1 d . . .
H14A H -0.2909 1.0152 -0.0187 0.092 Uiso 1 1 calc R . .
H14B H -0.1037 1.1104 0.0188 0.092 Uiso 1 1 calc R . .
H14C H -0.2582 1.1032 0.0836 0.092 Uiso 1 1 calc R . .
C15 C 0.1524(3) 0.6158(3) 0.4501(2) 0.0450(7) Uani 1 1 d . . .
H15 H 0.2433 0.5669 0.4476 0.058 Uiso 1 1 calc R . .
C16 C 0.1706(3) 0.6878(3) 0.5362(2) 0.0447(7) Uani 1 1 d . . .
H16 H 0.0739 0.7293 0.5428 0.058 Uiso 1 1 calc R . .
C17 C 0.3299(3) 0.7079(2) 0.62242(19) 0.0433(7) Uani 1 1 d . . .
C18 C 0.4627(4) 0.6294(3) 0.6342(2) 0.0530(8) Uani 1 1 d . . .
H18 H 0.4459 0.5564 0.5893 0.069 Uiso 1 1 calc R . .
C19 C 0.6185(4) 0.6573(3) 0.7110(2) 0.0619(9) Uani 1 1 d . . .
H19 H 0.7058 0.6034 0.7175 0.081 Uiso 1 1 calc R . .
C20 C 0.6454(4) 0.7646(3) 0.7780(2) 0.0636(9) Uani 1 1 d . . .
H20 H 0.7516 0.7842 0.8292 0.083 Uiso 1 1 calc R . .
C21 C 0.5154(4) 0.8425(3) 0.7691(2) 0.0644(9) Uani 1 1 d . . .
H21 H 0.5335 0.9153 0.8143 0.084 Uiso 1 1 calc R . .
C22 C 0.3587(4) 0.8138(3) 0.6936(2) 0.0556(8) Uani 1 1 d . . .
H22 H 0.2698 0.8660 0.6899 0.072 Uiso 1 1 calc R . .
C23 C -0.4218(3) 0.7396(3) 0.3087(2) 0.0503(8) Uani 1 1 d . . .
H23A H -0.4476 0.7062 0.3735 0.070 Uiso 1 1 calc R . .
H23B H -0.5126 0.6954 0.2516 0.070 Uiso 1 1 calc R . .
H23C H -0.4238 0.8319 0.3079 0.070 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O4 C12 115.8(2) . . ?
C13 O5 C14 116.3(2) . . ?
C2 N1 C9A 123.5(2) . . ?
C4 N3 C2 124.6(2) . . ?
N1 C2 N3 125.7(2) . . ?
N1 C2 C15 116.6(2) . . ?
N3 C2 C15 117.4(2) . . ?
N3 C4 C23 118.6(2) . . ?
N3 C4 C5 119.5(2) . . ?
C23 C4 C5 121.9(2) . . ?
C5A C5 C13 110.34(19) . . ?
C5A C5 C10 112.35(19) . . ?
C13 C5 C10 106.65(19) . . ?
C5A C5 C4 104.50(19) . . ?
C13 C5 C4 113.7(2) . . ?
C10 C5 C4 109.48(19) . . ?
C6 C5A C9A 118.4(2) . . ?
C6 C5A C5 122.5(2) . . ?
C9A C5A C5 119.1(2) . . ?
C7 C6 C5A 121.6(2) . . ?
C6 C7 C8 120.2(3) . . ?
C9 C8 C7 119.5(2) . . ?
C8 C9 C9A 121.7(3) . . ?
N1 C9A C9 115.9(2) . . ?
N1 C9A C5A 125.2(2) . . ?
C9 C9A C5A 118.6(2) . . ?
O2 C10 C11 121.5(2) . . ?
O2 C10 C5 124.3(2) . . ?
C11 C10 C5 114.0(2) . . ?
O3 C11 O4 125.4(2) . . ?
O3 C11 C10 120.9(2) . . ?
O4 C11 C10 113.7(2) . . ?
O1 C13 O5 123.3(2) . . ?
O1 C13 C5 126.5(2) . . ?
O5 C13 C5 110.1(2) . . ?
C16 C15 C2 126.9(2) . . ?
C15 C16 C17 125.6(2) . . ?
C18 C17 C22 117.2(2) . . ?
C18 C17 C16 122.7(2) . . ?
C22 C17 C16 120.0(2) . . ?
C19 C18 C17 121.3(3) . . ?
C20 C19 C18 120.1(3) . . ?
C21 C20 C19 119.8(3) . . ?
C20 C21 C22 120.3(3) . . ?
C21 C22 C17 121.3(3) . . ?
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 C13 1.189(3) . ?
O2 C10 1.197(3) . ?
O3 C11 1.194(3) . ?
O4 C11 1.306(3) . ?
O4 C12 1.451(3) . ?
O5 C13 1.336(3) . ?
O5 C14 1.449(3) . ?
N1 C2 1.295(3) . ?
N1 C9A 1.398(3) . ?
N3 C4 1.274(3) . ?
N3 C2 1.384(3) . ?
C2 C15 1.457(3) . ?
C4 C23 1.488(3) . ?
C4 C5 1.548(4) . ?
C5 C5A 1.521(3) . ?
C5 C13 1.533(3) . ?
C5 C10 1.543(3) . ?
C5A C6 1.388(3) . ?
C5A C9A 1.409(3) . ?
C6 C7 1.371(4) . ?
C7 C8 1.374(4) . ?
C8 C9 1.366(4) . ?
C9 C9A 1.398(4) . ?
C10 C11 1.523(4) . ?
C15 C16 1.317(4) . ?
C16 C17 1.462(4) . ?
C17 C18 1.388(4) . ?
C17 C22 1.394(4) . ?
C18 C19 1.375(4) . ?
C19 C20 1.373(4) . ?
C20 C21 1.368(4) . ?
C21 C22 1.371(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9793074
