#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/38/1503858.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_1503858
loop_
_publ_author_name
'Sasada, Toshiaki'
'Kobayashi, Fuminori'
'Sakai, Norio'
'Konakahara, Takeo'
_publ_section_title
;
 An unprecedented approach to 4,5-disubstituted pyrimidine derivatives by
 a ZnCl(2)-catalyzed three-component coupling reaction.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2161
_journal_page_last               2164
_journal_paper_doi               10.1021/ol900382j
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C14 H11 N3 O'
_chemical_formula_weight         237.26
_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                 92.403(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.613(3)
_cell_length_b                   9.682(5)
_cell_length_c                   21.629(10)
_cell_measurement_reflns_used    1515
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.98
_cell_measurement_theta_min      2.31
_cell_volume                     1174.4(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      273(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.922
_diffrn_measured_fraction_theta_max 0.922
_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  0.0558
_diffrn_reflns_av_sigmaI/netI    0.0672
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7004
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  -183
_exptl_absorpt_correction_T_min  -183
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.311
_refine_ls_hydrogen_treatment    calc
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2694
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.311
_refine_ls_R_factor_all          0.1219
_refine_ls_R_factor_gt           0.1099
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0556P)²+2.4695P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2184
_refine_ls_wR_factor_ref         0.2240
_reflns_number_gt                2356
_reflns_number_total             2694
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900382j_si_001.cif
_cod_data_source_block           4a
_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_cell_volume        1174.4(9)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1503858
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 -0.1507(4) 0.6646(3) 0.07951(12) 0.0210(6) Uani 1 1 d .
N3 N 0.0283(5) 1.1388(3) 0.11067(13) 0.0165(6) Uani 1 1 d .
N2 N -0.2841(5) 1.0783(3) 0.03801(14) 0.0183(7) Uani 1 1 d .
C5 C -0.0423(6) 0.9022(3) 0.08720(15) 0.0141(7) Uani 1 1 d .
N1 N -0.0485(5) 0.5322(3) 0.07579(15) 0.0218(7) Uani 1 1 d .
C12 C 0.2299(6) 0.8747(4) 0.21527(17) 0.0179(7) Uani 1 1 d .
H12 H 0.0993 0.8157 0.2112 0.022 Uiso 1 1 calc R
C9 C 0.6207(6) 1.0484(4) 0.22761(18) 0.0227(8) Uani 1 1 d .
H9 H 0.7540 1.1054 0.2313 0.027 Uiso 1 1 calc R
C1 C 0.3480(7) 0.4318(4) 0.07857(19) 0.0234(8) Uani 1 1 d .
H1A H 0.2619 0.3470 0.0831 0.035 Uiso 1 1 calc R
H1B H 0.4677 0.4397 0.1114 0.035 Uiso 1 1 calc R
H1C H 0.4228 0.4322 0.0395 0.035 Uiso 1 1 calc R
C14 C -0.2279(6) 0.9467(4) 0.04721(16) 0.0166(7) Uani 1 1 d .
H14 H -0.3175 0.8801 0.0257 0.020 Uiso 1 1 calc R
C4 C 0.0269(6) 0.7572(4) 0.08736(15) 0.0151(7) Uani 1 1 d .
C7 C 0.2594(6) 0.9797(3) 0.17233(15) 0.0149(7) Uani 1 1 d .
C6 C 0.0778(6) 1.0057(3) 0.12168(15) 0.0139(7) Uani 1 1 d .
C10 C 0.5897(7) 0.9448(4) 0.26986(17) 0.0263(9) Uani 1 1 d .
H10 H 0.7003 0.9330 0.3027 0.032 Uiso 1 1 calc R
C2 C 0.1795(6) 0.5508(4) 0.08134(16) 0.0175(7) Uani 1 1 d .
C8 C 0.4535(6) 1.0680(4) 0.17959(16) 0.0174(7) Uani 1 1 d .
H8 H 0.4713 1.1406 0.1520 0.021 Uiso 1 1 calc R
C3 C 0.2375(6) 0.6919(3) 0.08970(16) 0.0172(7) Uani 1 1 d .
H3 H 0.3883 0.7307 0.0955 0.021 Uiso 1 1 calc R
C11 C 0.3946(7) 0.8580(4) 0.26384(17) 0.0235(8) Uani 1 1 d .
H11 H 0.3743 0.7881 0.2926 0.028 Uiso 1 1 calc R
C13 C -0.1459(6) 1.1675(3) 0.06918(16) 0.0165(7) Uani 1 1 d .
H13 H -0.1741 1.2606 0.0611 0.020 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
C4 O1 N1 108.2(3)
C13 N3 C6 117.6(3)
C14 N2 C13 114.8(3)
C14 C5 C6 116.0(3)
C14 C5 C4 119.4(3)
C6 C5 C4 124.4(3)
C2 N1 O1 105.8(3)
C11 C12 C7 119.9(3)
C10 C9 C8 119.9(3)
N2 C14 C5 123.9(3)
C3 C4 O1 109.8(3)
C3 C4 C5 133.6(3)
O1 C4 C5 116.4(3)
C8 C7 C12 119.3(3)
C8 C7 C6 119.3(3)
C12 C7 C6 121.2(3)
N3 C6 C5 120.1(3)
N3 C6 C7 115.2(3)
C5 C6 C7 124.7(3)
C9 C10 C11 120.3(3)
N1 C2 C3 111.6(3)
N1 C2 C1 121.0(3)
C3 C2 C1 127.4(3)
C9 C8 C7 120.3(3)
C4 C3 C2 104.7(3)
C12 C11 C10 120.3(4)
N2 C13 N3 127.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.346(4)
O1 N1 1.408(4)
N3 C13 1.329(4)
N3 C6 1.338(4)
N2 C14 1.325(4)
N2 C13 1.326(4)
C5 C14 1.394(5)
C5 C6 1.404(5)
C5 C4 1.457(5)
N1 C2 1.293(5)
C12 C11 1.379(5)
C12 C7 1.392(5)
C9 C10 1.373(6)
C9 C8 1.383(5)
C1 C2 1.493(5)
C4 C3 1.340(5)
C7 C8 1.389(5)
C7 C6 1.486(5)
C10 C11 1.382(6)
C2 C3 1.414(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 28415754
