#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/91/2229104.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2229104
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Sumangala, V.'
'Prasad, D. Jagadeesh'
'Poojary, Boja'
'Chantrapromma, Suchada'
_publ_section_title
;
 Methyl
 2-[2-(benzyloxycarbonylamino)propan-2-yl]-5-hydroxy-6-methoxypyrimidine-4-carboxylate
;
_journal_coeditor_code           IS2653
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o274
_journal_paper_doi               10.1107/S160053681005467X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C18 H21 N3 O6'
_chemical_formula_moiety         'C18 H21 N3 O6'
_chemical_formula_sum            'C18 H21 N3 O6'
_chemical_formula_weight         375.38
_chemical_melting_point_gt       391
_chemical_melting_point_lt       393
_chemical_name_systematic
'Methyl 2-[2-(benzyloxycarbonylamino)propan-2-yl]-5-hydroxy-6-methoxypyrimidine-4-carboxylate'
_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                 97.2360(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.5226(2)
_cell_length_b                   8.57170(10)
_cell_length_c                   13.0944(2)
_cell_measurement_reflns_used    5348
_cell_measurement_temperature    297
_cell_measurement_theta_max      29.99
_cell_measurement_theta_min      2.49
_cell_volume                     1839.75(4)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      297
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20111
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         2.49
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9605
_exptl_absorpt_correction_T_min  0.9438
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.325
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         5348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0539
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0839P)²+0.5187P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1642
_reflns_number_gt                4087
_reflns_number_total             5348
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2653.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229104
_cod_database_fobs_code          2229104
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.33157(8) 0.66001(18) 0.07370(11) 0.0657(4) Uani d . 1 . .
O O2 0.24087(8) 0.48066(17) 0.11686(10) 0.0576(3) Uani d . 1 . .
O O3 0.06818(6) 0.74259(11) -0.14162(9) 0.0416(3) Uani d . 1 . .
O O4 -0.06047(6) 0.56031(12) -0.13886(9) 0.0417(3) Uani d . 1 . .
O O5 -0.10852(6) 0.26969(13) -0.11206(10) 0.0473(3) Uani d . 1 . .
O O6 -0.01903(6) 0.07581(11) -0.11913(8) 0.0393(2) Uani d . 1 . .
N N1 0.30737(7) 0.45068(16) -0.02407(11) 0.0407(3) Uani d . 1 . .
N N2 0.15729(7) 0.53687(13) -0.11038(9) 0.0355(3) Uani d . 1 . .
N N3 0.10782(7) 0.27843(13) -0.09593(9) 0.0335(2) Uani d . 1 . .
C C1 0.43521(17) 0.8804(4) 0.2532(3) 0.0946(9) Uani d . 1 . .
H H1A 0.4369 0.9541 0.2015 0.114 Uiso calc R 1 . .
C C2 0.49368(19) 0.8838(5) 0.3419(3) 0.1240(13) Uani d . 1 . .
H H2A 0.5334 0.9611 0.3500 0.149 Uiso calc R 1 . .
C C3 0.49077(19) 0.7724(5) 0.4147(3) 0.1109(12) Uani d . 1 . .
H H3A 0.5300 0.7721 0.4723 0.133 Uiso calc R 1 . .
C C4 0.43242(19) 0.6625(5) 0.4054(2) 0.1040(10) Uani d . 1 . .
H H4A 0.4310 0.5876 0.4566 0.125 Uiso calc R 1 . .
C C5 0.37474(15) 0.6607(3) 0.3200(2) 0.0802(7) Uani d . 1 . .
H H5A 0.3342 0.5848 0.3144 0.096 Uiso calc R 1 . .
C C6 0.37579(10) 0.7669(2) 0.24422(15) 0.0554(4) Uani d . 1 . .
C C7 0.31165(14) 0.7682(3) 0.15168(18) 0.0690(6) Uani d . 1 . .
H H7A 0.2593 0.7402 0.1727 0.083 Uiso calc R 1 . .
H H7B 0.3070 0.8727 0.1230 0.083 Uiso calc R 1 . .
C C8 0.28785(9) 0.5255(2) 0.06047(12) 0.0438(3) Uani d . 1 . .
C C9 0.25579(8) 0.32633(17) -0.07422(12) 0.0402(3) Uani d . 1 . .
C C10 0.16670(8) 0.38177(15) -0.09313(10) 0.0334(3) Uani d . 1 . .
C C11 0.08266(8) 0.59052(15) -0.12577(10) 0.0331(3) Uani d . 1 . .
C C12 0.01324(8) 0.49250(15) -0.12617(10) 0.0319(3) Uani d . 1 . .
C C13 0.03020(8) 0.33494(15) -0.11279(10) 0.0306(3) Uani d . 1 . .
C C14 -0.03910(8) 0.22435(15) -0.11428(10) 0.0327(3) Uani d . 1 . .
C C15 -0.08544(9) -0.03516(18) -0.11987(13) 0.0428(3) Uani d . 1 . .
H H15A -0.0688 -0.1342 -0.1443 0.064 Uiso calc R 1 . .
H H15B -0.1320 0.0021 -0.1645 0.064 Uiso calc R 1 . .
H H15C -0.0995 -0.0467 -0.0513 0.064 Uiso calc R 1 . .
C C16 0.28446(11) 0.2973(3) -0.17910(16) 0.0620(5) Uani d . 1 . .
H H16A 0.2781 0.3910 -0.2195 0.093 Uiso calc R 1 . .
H H16B 0.2524 0.2154 -0.2141 0.093 Uiso calc R 1 . .
H H16C 0.3409 0.2672 -0.1696 0.093 Uiso calc R 1 . .
C C17 0.26450(10) 0.1795(2) -0.00690(18) 0.0621(5) Uani d . 1 . .
H H17A 0.2431 0.1996 0.0567 0.093 Uiso calc R 1 . .
H H17B 0.3211 0.1517 0.0072 0.093 Uiso calc R 1 . .
H H17C 0.2348 0.0953 -0.0424 0.093 Uiso calc R 1 . .
C C18 0.13886(10) 0.84324(18) -0.13387(14) 0.0459(4) Uani d . 1 . .
H H18A 0.1215 0.9500 -0.1412 0.069 Uiso calc R 1 . .
H H18B 0.1714 0.8175 -0.1873 0.069 Uiso calc R 1 . .
H H18C 0.1706 0.8291 -0.0679 0.069 Uiso calc R 1 . .
H H1N1 0.3337(13) 0.501(3) -0.0634(16) 0.056(6) Uiso d . 1 . .
H H1O4 -0.0985(14) 0.492(3) -0.1310(16) 0.061(6) Uiso d . 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 O1 C7 . . 117.95(16) ?
C11 O3 C18 . . 116.35(11) ?
C12 O4 H1O4 . . 110.4(15) ?
C14 O6 C15 . . 116.01(11) ?
C8 N1 C9 . . 121.72(13) ?
C8 N1 H1N1 . . 117.3(15) ?
C9 N1 H1N1 . . 114.6(15) ?
C11 N2 C10 . . 117.20(12) ?
C10 N3 C13 . . 116.34(11) ?
C6 C1 C2 . . 119.4(3) ?
C6 C1 H1A . . 120.3 ?
C2 C1 H1A . . 120.3 ?
C3 C2 C1 . . 118.8(3) ?
C3 C2 H2A . . 120.6 ?
C1 C2 H2A . . 120.6 ?
C4 C3 C2 . . 121.3(3) ?
C4 C3 H3A . . 119.3 ?
C2 C3 H3A . . 119.3 ?
C3 C4 C5 . . 119.9(3) ?
C3 C4 H4A . . 120.1 ?
C5 C4 H4A . . 120.1 ?
C6 C5 C4 . . 121.3(3) ?
C6 C5 H5A . . 119.4 ?
C4 C5 H5A . . 119.4 ?
C5 C6 C1 . . 119.3(2) ?
C5 C6 C7 . . 121.61(19) ?
C1 C6 C7 . . 119.1(2) ?
O1 C7 C6 . . 111.30(17) ?
O1 C7 H7A . . 109.4 ?
C6 C7 H7A . . 109.4 ?
O1 C7 H7B . . 109.4 ?
C6 C7 H7B . . 109.4 ?
H7A C7 H7B . . 108.0 ?
O2 C8 N1 . . 126.21(16) ?
O2 C8 O1 . . 124.59(16) ?
N1 C8 O1 . . 109.19(14) ?
N1 C9 C16 . . 106.99(13) ?
N1 C9 C17 . . 109.39(13) ?
C16 C9 C17 . . 111.45(16) ?
N1 C9 C10 . . 109.75(11) ?
C16 C9 C10 . . 107.73(12) ?
C17 C9 C10 . . 111.42(13) ?
N3 C10 N2 . . 126.07(12) ?
N3 C10 C9 . . 119.16(12) ?
N2 C10 C9 . . 114.70(12) ?
N2 C11 O3 . . 120.91(12) ?
N2 C11 C12 . . 122.52(12) ?
O3 C11 C12 . . 116.57(12) ?
O4 C12 C13 . . 127.17(12) ?
O4 C12 C11 . . 117.66(12) ?
C13 C12 C11 . . 115.17(12) ?
N3 C13 C12 . . 122.55(12) ?
N3 C13 C14 . . 118.93(11) ?
C12 C13 C14 . . 118.50(11) ?
O5 C14 O6 . . 123.62(13) ?
O5 C14 C13 . . 121.63(12) ?
O6 C14 C13 . . 114.75(11) ?
O6 C15 H15A . . 109.5 ?
O6 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O6 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C9 C16 H16A . . 109.5 ?
C9 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C9 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C9 C17 H17A . . 109.5 ?
C9 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C9 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
O3 C18 H18A . . 109.5 ?
O3 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
O3 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C8 . 1.360(2) ?
O1 C7 . 1.448(3) ?
O2 C8 . 1.200(2) ?
O3 C11 . 1.3368(16) ?
O3 C18 . 1.4452(18) ?
O4 C12 . 1.3408(16) ?
O4 H1O4 . 0.88(2) ?
O5 C14 . 1.2149(17) ?
O6 C14 . 1.3193(16) ?
O6 C15 . 1.4513(17) ?
N1 C8 . 1.353(2) ?
N1 C9 . 1.4672(19) ?
N1 H1N1 . 0.83(2) ?
N2 C11 . 1.3077(17) ?
N2 C10 . 1.3542(17) ?
N3 C10 . 1.3127(17) ?
N3 C13 . 1.3627(16) ?
C1 C6 . 1.376(3) ?
C1 C2 . 1.414(5) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.354(5) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.343(5) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.375(4) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.349(3) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.506(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C9 C16 . 1.529(2) ?
C9 C17 . 1.533(2) ?
C9 C10 . 1.5370(18) ?
C11 C12 . 1.4213(19) ?
C12 C13 . 1.3860(18) ?
C13 C14 . 1.4847(18) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O4 H1O4 O5 1_555 0.87(2) 1.93(3) 2.6513(15) 139(2) y
O4 H1O4 O2 3_565 0.87(2) 2.39(2) 3.0508(17) 132(2) y
C7 H7A O5 3_565 0.97 2.52 3.347(3) 143 y
C15 H15A O3 1_545 0.96 2.49 3.2148(18) 132 y
C17 H17A O2 1_555 0.96 2.54 3.099(2) 117 y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 1.6(5) ?
C1 C2 C3 C4 . . . . -1.8(6) ?
C2 C3 C4 C5 . . . . 0.7(6) ?
C3 C4 C5 C6 . . . . 0.6(5) ?
C4 C5 C6 C1 . . . . -0.8(4) ?
C4 C5 C6 C7 . . . . -178.5(2) ?
C2 C1 C6 C5 . . . . -0.3(4) ?
C2 C1 C6 C7 . . . . 177.4(3) ?
C8 O1 C7 C6 . . . . 106.6(2) ?
C5 C6 C7 O1 . . . . -84.3(3) ?
C1 C6 C7 O1 . . . . 98.0(3) ?
C9 N1 C8 O2 . . . . 18.1(2) ?
C9 N1 C8 O1 . . . . -163.27(13) ?
C7 O1 C8 O2 . . . . -9.7(2) ?
C7 O1 C8 N1 . . . . 171.67(15) ?
C8 N1 C9 C16 . . . . 166.62(15) ?
C8 N1 C9 C17 . . . . -72.52(18) ?
C8 N1 C9 C10 . . . . 50.01(18) ?
C13 N3 C10 N2 . . . . -3.5(2) ?
C13 N3 C10 C9 . . . . 179.89(12) ?
C11 N2 C10 N3 . . . . 4.0(2) ?
C11 N2 C10 C9 . . . . -179.24(12) ?
N1 C9 C10 N3 . . . . -151.85(13) ?
C16 C9 C10 N3 . . . . 92.00(17) ?
C17 C9 C10 N3 . . . . -30.53(19) ?
N1 C9 C10 N2 . . . . 31.13(17) ?
C16 C9 C10 N2 . . . . -85.01(16) ?
C17 C9 C10 N2 . . . . 152.45(14) ?
C10 N2 C11 O3 . . . . 178.86(12) ?
C10 N2 C11 C12 . . . . -0.8(2) ?
C18 O3 C11 N2 . . . . -3.98(19) ?
C18 O3 C11 C12 . . . . 175.74(12) ?
N2 C11 C12 O4 . . . . 177.56(12) ?
O3 C11 C12 O4 . . . . -2.16(18) ?
N2 C11 C12 C13 . . . . -2.25(19) ?
O3 C11 C12 C13 . . . . 178.04(12) ?
C10 N3 C13 C12 . . . . -0.14(19) ?
C10 N3 C13 C14 . . . . -178.53(11) ?
O4 C12 C13 N3 . . . . -177.02(12) ?
C11 C12 C13 N3 . . . . 2.76(19) ?
O4 C12 C13 C14 . . . . 1.4(2) ?
C11 C12 C13 C14 . . . . -178.85(11) ?
C15 O6 C14 O5 . . . . -1.1(2) ?
C15 O6 C14 C13 . . . . 179.53(11) ?
N3 C13 C14 O5 . . . . 167.78(13) ?
C12 C13 C14 O5 . . . . -10.7(2) ?
N3 C13 C14 O6 . . . . -12.83(17) ?
C12 C13 C14 O6 . . . . 168.72(12) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 28293229
