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#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/39/4023953.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_4023953
loop_
_publ_author_name
'Blanca R. Díaz-Sánchez'
'Martín A. Iglesias-Arteaga'
'Roberto Melgar-Fernández'
'Eusebio Juaristi'
_publ_contact_author_address
;     Departamento de Química
      Centro de Investigación y de Estudios Avanzados
      Instituto Politécnico Nacional
      Apartado Postal 14-740      
      07000 México D.F.
      Mexico
;
_publ_contact_author_email       juaristi@relaq.mx
_publ_contact_author_fax         (+52)(55)57477132
_publ_contact_author_name        'Eusebio Juaristi'
_publ_contact_author_phone       (+52)(55)50613722
_publ_section_title
;
 Synthesis of 2-Substituted-5-halo-2,3-dihydro-4(H)-pyrimidin-4-ones
 and Their Derivatization Utilizing the Sonogashira Coupling Reaction
 in the Enantioselective Synthesis of α-Substituted
 β-Amino Acids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4822
_journal_page_last               4825
_journal_paper_doi               10.1021/jo0705115
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C14 H15 Br1 N2 O2'
_chemical_formula_sum            'C14 H15 Br N2 O2'
_chemical_formula_weight         323.19
_chemical_melting_point          469
_chemical_name_systematic
;
1-Benzoyl-2(S)-iso-propyl-5-bromo-2,3-dihydro-4(H)-pyrimidin-4-one
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2004-12-07
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.9920(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.4454(4)
_cell_length_b                   7.2110(2)
_cell_length_c                   14.2431(5)
_cell_measurement_reflns_used    2974
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      3.395
_cell_volume                     1426.23(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'HKL Denzo (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0579
_diffrn_reflns_av_sigmaI/netI    0.0552
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5145
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.56
_diffrn_standards_number         5145
_exptl_absorpt_coefficient_mu    2.882
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.864
_refine_diff_density_min         -0.808
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.011(12)
_refine_ls_extinction_coef       0.0106(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2842
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0405
_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)+(0.0600P)²+0.1706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                2647
_reflns_number_total             2842
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0705115si20070313_011453_2.cif
_cod_data_source_block           ejbd02
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4023953
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, 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
C9 C 0.5043(4) 0.5463(8) 0.1300(3) 0.0635(12) Uani 1 1 d . . .
H9A H 0.5546 0.6173 0.1150 0.095 Uiso 1 1 calc R . .
H9B H 0.4430 0.6014 0.0987 0.095 Uiso 1 1 calc R . .
H9C H 0.5058 0.4216 0.1069 0.095 Uiso 1 1 calc R . .
C10 C 0.4402(4) 0.4307(7) 0.2652(5) 0.0731(15) Uani 1 1 d . . .
H10A H 0.4404 0.3075 0.2398 0.110 Uiso 1 1 calc R . .
H10B H 0.3790 0.4879 0.2362 0.110 Uiso 1 1 calc R . .
H10C H 0.4512 0.4250 0.3348 0.110 Uiso 1 1 calc R . .
C15 C 0.6510(3) 1.1510(6) 0.0780(3) 0.0485(10) Uani 1 1 d . . .
H15 H 0.6117 1.0841 0.0264 0.058 Uiso 1 1 calc R . .
O7 O 0.63438(17) 0.6960(6) 0.53993(14) 0.0464(5) Uani 1 1 d . . .
C2 C 0.5217(2) 0.7413(5) 0.2820(2) 0.0339(8) Uani 1 1 d . . .
H2 H 0.4597 0.8003 0.2511 0.041 Uiso 1 1 calc R . .
C4 C 0.6230(2) 0.7214(5) 0.4517(2) 0.0355(7) Uani 1 1 d . . .
C5 C 0.7040(2) 0.7465(5) 0.4082(2) 0.0349(8) Uani 1 1 d . . .
C6 C 0.6910(3) 0.8234(5) 0.3211(2) 0.0353(7) Uani 1 1 d . . .
C8 C 0.5194(3) 0.5441(6) 0.2413(3) 0.0442(9) Uani 1 1 d . . .
H8 H 0.5813 0.4846 0.2720 0.053 Uiso 1 1 calc R . .
C11 C 0.5740(3) 0.9855(6) 0.1870(3) 0.0415(8) Uani 1 1 d . . .
C14 C 0.6487(2) 1.1161(5) 0.1733(2) 0.0380(7) Uani 1 1 d . . .
C16 C 0.7125(3) 1.2864(7) 0.0603(3) 0.0545(11) Uani 1 1 d . . .
H16 H 0.7158 1.3073 -0.0032 0.065 Uiso 1 1 calc R . .
C17 C 0.7690(3) 1.3905(7) 0.1364(3) 0.0541(10) Uani 1 1 d . . .
H17 H 0.8086 1.4833 0.1238 0.065 Uiso 1 1 calc R . .
C18 C 0.7666(3) 1.3567(6) 0.2311(3) 0.0482(9) Uani 1 1 d . . .
H18 H 0.8042 1.4271 0.2822 0.058 Uiso 1 1 calc R . .
C19 C 0.7080(2) 1.2171(7) 0.2497(2) 0.0404(8) Uani 1 1 d . . .
H19 H 0.7083 1.1909 0.3137 0.048 Uiso 1 1 calc R . .
Br13 Br 0.82961(2) 0.69894(5) 0.48650(2) 0.04783(17) Uani 1 1 d . . .
N1 N 0.5978(2) 0.8556(4) 0.2619(2) 0.0356(6) Uani 1 1 d . . .
N3 N 0.5359(2) 0.7431(4) 0.38748(19) 0.0381(7) Uani 1 1 d D . .
O12 O 0.4917(2) 0.9946(5) 0.1345(2) 0.0573(8) Uani 1 1 d . . .
H3 H 0.490(4) 0.741(11) 0.417(5) 0.12(2) Uiso 1 1 d D . .
H6 H 0.740(3) 0.843(6) 0.293(3) 0.044(11) 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'
Br Br -0.2901 2.4595 '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
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 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C15 C14 119.5(4) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
N3 C2 N1 107.2(3) . . ?
N3 C2 C8 112.3(3) . . ?
N1 C2 C8 112.8(3) . . ?
N3 C2 H2 108.1 . . ?
N1 C2 H2 108.1 . . ?
C8 C2 H2 108.1 . . ?
O7 C4 N3 123.2(3) . . ?
O7 C4 C5 123.0(3) . . ?
N3 C4 C5 113.6(3) . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 Br13 119.8(3) . . ?
C4 C5 Br13 118.3(2) . . ?
C5 C6 N1 119.9(3) . . ?
C5 C6 H6 123(3) . . ?
N1 C6 H6 116(3) . . ?
C10 C8 C2 110.8(3) . . ?
C10 C8 C9 109.5(4) . . ?
C2 C8 C9 111.2(4) . . ?
C10 C8 H8 108.4 . . ?
C2 C8 H8 108.4 . . ?
C9 C8 H8 108.4 . . ?
O12 C11 N1 120.1(4) . . ?
O12 C11 C14 120.4(3) . . ?
N1 C11 C14 119.5(3) . . ?
C15 C14 C19 119.7(4) . . ?
C15 C14 C11 117.2(3) . . ?
C19 C14 C11 122.8(3) . . ?
C17 C16 C15 120.5(4) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 120.1(4) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 119.8(4) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C14 120.4(3) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
C11 N1 C6 124.7(3) . . ?
C11 N1 C2 119.2(3) . . ?
C6 N1 C2 116.1(3) . . ?
C4 N3 C2 122.7(3) . . ?
C4 N3 H3 111(5) . . ?
C2 N3 H3 126(5) . . ?
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
C9 C8 1.541(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C8 1.519(7) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C15 C16 1.389(6) . ?
C15 C14 1.390(5) . ?
C15 H15 0.9300 . ?
O7 C4 1.235(4) . ?
C2 N3 1.460(4) . ?
C2 N1 1.464(5) . ?
C2 C8 1.532(5) . ?
C2 H2 0.9800 . ?
C4 N3 1.345(4) . ?
C4 C5 1.480(5) . ?
C5 C6 1.325(5) . ?
C5 Br13 1.881(3) . ?
C6 N1 1.397(4) . ?
C6 H6 0.91(5) . ?
C8 H8 0.9800 . ?
C11 O12 1.219(4) . ?
C11 N1 1.389(5) . ?
C11 C14 1.486(5) . ?
C14 C19 1.391(5) . ?
C16 C17 1.385(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.387(6) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
N3 H3 0.89(2) . ?
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
O7 C4 C5 C6 -160.9(4) . . . . ?
N3 C4 C5 C6 14.3(5) . . . . ?
O7 C4 C5 Br13 10.4(5) . . . . ?
N3 C4 C5 Br13 -174.5(3) . . . . ?
C4 C5 C6 N1 -10.2(6) . . . . ?
Br13 C5 C6 N1 178.7(3) . . . . ?
N3 C2 C8 C10 57.9(5) . . . . ?
N1 C2 C8 C10 179.3(4) . . . . ?
N3 C2 C8 C9 180.0(3) . . . . ?
N1 C2 C8 C9 -58.7(4) . . . . ?
C16 C15 C14 C19 0.0(6) . . . . ?
C16 C15 C14 C11 173.2(4) . . . . ?
O12 C11 C14 C15 -43.3(6) . . . . ?
N1 C11 C14 C15 138.3(4) . . . . ?
O12 C11 C14 C19 129.8(5) . . . . ?
N1 C11 C14 C19 -48.6(6) . . . . ?
C14 C15 C16 C17 -2.1(7) . . . . ?
C15 C16 C17 C18 1.9(7) . . . . ?
C16 C17 C18 C19 0.5(7) . . . . ?
C17 C18 C19 C14 -2.6(6) . . . . ?
C15 C14 C19 C18 2.4(6) . . . . ?
C11 C14 C19 C18 -170.5(4) . . . . ?
O12 C11 N1 C6 174.7(4) . . . . ?
C14 C11 N1 C6 -6.9(6) . . . . ?
O12 C11 N1 C2 -5.1(6) . . . . ?
C14 C11 N1 C2 173.2(3) . . . . ?
C5 C6 N1 C11 157.5(4) . . . . ?
C5 C6 N1 C2 -22.7(5) . . . . ?
N3 C2 N1 C11 -133.5(3) . . . . ?
C8 C2 N1 C11 102.3(4) . . . . ?
N3 C2 N1 C6 46.6(4) . . . . ?
C8 C2 N1 C6 -77.5(4) . . . . ?
O7 C4 N3 C2 -169.3(4) . . . . ?
C5 C4 N3 C2 15.6(5) . . . . ?
N1 C2 N3 C4 -44.6(4) . . . . ?
C8 C2 N3 C4 79.9(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 20564602
