#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/08/2220828.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_2220828
loop_
_publ_author_name
'Wang, Xing-Han'
'Hao, Wen-Juan'
'Tu, Shu-Jiang'
_publ_section_title
N-Cyclohexyl-3-(4-hydroxy-6-oxo-1,6-dihydropyrimidin-5-yl)-3-p-tolylpropanamide
_journal_coeditor_code           HK2610
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o309
_journal_paper_doi               10.1107/S1600536809001251
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H25 N3 O3'
_chemical_formula_moiety         'C20 H25 N3 O3'
_chemical_formula_sum            'C20 H25 N3 O3'
_chemical_formula_weight         355.43
_chemical_melting_point_gt       534
_chemical_melting_point_lt       536
_chemical_name_systematic
;
N-Cyclohexyl-3-(4-hydroxy-6-oxo-1,6-dihydropyrimidin-5-yl)-
3-p-tolylpropanamide
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 101.740(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1563(12)
_cell_length_b                   19.637(2)
_cell_length_c                   13.2746(18)
_cell_measurement_reflns_used    1921
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.66
_cell_measurement_theta_min      2.6
_cell_volume                     1826.4(4)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  'SHELXTL (Bruker, 1998)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0733
_diffrn_reflns_av_sigmaI/netI    0.0752
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9491
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9878
_exptl_absorpt_correction_T_min  0.9800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.194
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3216
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0354P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.1042
_reflns_number_gt                1916
_reflns_number_total             3216
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2610.cif
_cod_data_source_block           I
_cod_original_cell_volume        1826.5(4)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2220828
_cod_database_fobs_code          2220828
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_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 0.8327(2) 1.04303(8) 0.89288(11) 0.0456(5) Uani d . 1 . .
H H1A 0.8598 1.0297 0.9526 0.068 Uiso calc R 1 . .
O O2 1.1335(2) 1.04358(9) 0.60752(11) 0.0511(5) Uani d . 1 . .
O O3 0.5892(2) 0.93937(8) 0.69802(11) 0.0447(4) Uani d . 1 . .
N N1 1.2782(3) 1.00038(10) 0.76292(14) 0.0387(5) Uani d . 1 . .
H H1 1.3786 0.9909 0.7394 0.046 Uiso calc R 1 . .
N N2 1.1340(3) 0.99789(9) 0.90587(13) 0.0367(5) Uani d . 1 . .
N N3 0.7956(3) 0.91122(9) 0.59665(13) 0.0378(5) Uani d . 1 . .
H H3 0.8514 0.9251 0.5488 0.045 Uiso calc R 1 . .
C C1 1.2753(3) 0.98462(12) 0.86043(17) 0.0396(6) Uani d . 1 . .
H H1B 1.3815 0.9626 0.8987 0.048 Uiso calc R 1 . .
C C2 0.9778(3) 1.02944(11) 0.84599(16) 0.0316(5) Uani d . 1 . .
C C3 0.9650(3) 1.04690(10) 0.74467(15) 0.0290(5) Uani d . 1 . .
C C4 1.1234(3) 1.03189(11) 0.69730(17) 0.0346(6) Uani d . 1 . .
C C5 0.6857(3) 0.95565(11) 0.63376(16) 0.0329(6) Uani d . 1 . .
C C6 0.6872(3) 1.02749(11) 0.59477(16) 0.0350(6) Uani d . 1 . .
H H6A 0.5572 1.0422 0.5679 0.042 Uiso calc R 1 . .
H H6B 0.7563 1.0291 0.5391 0.042 Uiso calc R 1 . .
C C7 0.7820(3) 1.07626(11) 0.68124(15) 0.0317(6) Uani d . 1 . .
H H7 0.6931 1.0795 0.7283 0.038 Uiso calc R 1 . .
C C8 0.8005(3) 1.14835(11) 0.64204(16) 0.0302(5) Uani d . 1 . .
C C9 0.6815(3) 1.17248(12) 0.55327(17) 0.0366(6) Uani d . 1 . .
H H9 0.6022 1.1421 0.5108 0.044 Uiso calc R 1 . .
C C10 0.6781(3) 1.24068(12) 0.52658(18) 0.0400(6) Uani d . 1 . .
H H10 0.5952 1.2553 0.4672 0.048 Uiso calc R 1 . .
C C11 0.7955(4) 1.28759(12) 0.58638(19) 0.0393(6) Uani d . 1 . .
C C12 0.9218(4) 1.26311(12) 0.67173(19) 0.0412(6) Uani d . 1 . .
H H12 1.0068 1.2931 0.7115 0.049 Uiso calc R 1 . .
C C13 0.9251(3) 1.19530(12) 0.69940(17) 0.0367(6) Uani d . 1 . .
H H13 1.0118 1.1806 0.7573 0.044 Uiso calc R 1 . .
C C14 0.7807(4) 1.36269(12) 0.5595(2) 0.0587(8) Uani d . 1 . .
H H14A 0.8643 1.3731 0.5135 0.088 Uiso calc R 1 . .
H H14B 0.8168 1.3892 0.6212 0.088 Uiso calc R 1 . .
H H14C 0.6517 1.3734 0.5269 0.088 Uiso calc R 1 . .
C C15 0.8280(3) 0.84081(11) 0.63122(17) 0.0367(6) Uani d . 1 . .
H H15 0.7200 0.8266 0.6614 0.044 Uiso calc R 1 . .
C C16 1.0092(4) 0.83383(13) 0.71338(18) 0.0488(7) Uani d . 1 . .
H H16A 0.9999 0.8627 0.7714 0.059 Uiso calc R 1 . .
H H16B 1.1174 0.8492 0.6857 0.059 Uiso calc R 1 . .
C C17 1.0429(4) 0.76056(13) 0.75025(19) 0.0532(7) Uani d . 1 . .
H H17A 1.1649 0.7576 0.7979 0.064 Uiso calc R 1 . .
H H17B 0.9442 0.7473 0.7868 0.064 Uiso calc R 1 . .
C C18 1.0418(4) 0.71171(14) 0.6614(2) 0.0593(8) Uani d . 1 . .
H H18A 1.1538 0.7198 0.6324 0.071 Uiso calc R 1 . .
H H18B 1.0483 0.6653 0.6869 0.071 Uiso calc R 1 . .
C C19 0.8642(4) 0.72005(12) 0.5780(2) 0.0556(8) Uani d . 1 . .
H H19A 0.7536 0.7057 0.6043 0.067 Uiso calc R 1 . .
H H19B 0.8738 0.6910 0.5202 0.067 Uiso calc R 1 . .
C C20 0.8367(4) 0.79365(12) 0.54125(18) 0.0435(6) Uani d . 1 . .
H H20A 0.9418 0.8070 0.5095 0.052 Uiso calc R 1 . .
H H20B 0.7195 0.7975 0.4900 0.052 Uiso calc R 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
C1 N1 C4 . . 122.5(2) ?
C1 N1 H1 . . 118.8 ?
C4 N1 H1 . . 118.8 ?
C1 N2 C2 . . 115.89(18) ?
C5 N3 C15 . . 124.82(18) ?
C5 N3 H3 . . 117.6 ?
C15 N3 H3 . . 117.6 ?
C2 O1 H1A . . 109.5 ?
N2 C1 N1 . . 124.6(2) ?
N2 C1 H1B . . 117.7 ?
N1 C1 H1B . . 117.7 ?
O1 C2 C3 . . 120.1(2) ?
O1 C2 N2 . . 115.78(18) ?
C3 C2 N2 . . 124.1(2) ?
C2 C3 C4 . . 118.5(2) ?
C2 C3 C7 . . 121.06(19) ?
C4 C3 C7 . . 120.26(18) ?
O2 C4 N1 . . 119.2(2) ?
O2 C4 C3 . . 126.4(2) ?
N1 C4 C3 . . 114.34(18) ?
O3 C5 N3 . . 122.4(2) ?
O3 C5 C6 . . 121.4(2) ?
N3 C5 C6 . . 116.14(19) ?
C5 C6 C7 . . 111.05(17) ?
C5 C6 H6A . . 109.4 ?
C7 C6 H6A . . 109.4 ?
C5 C6 H6B . . 109.4 ?
C7 C6 H6B . . 109.4 ?
H6A C6 H6B . . 108.0 ?
C3 C7 C8 . . 114.65(18) ?
C3 C7 C6 . . 112.09(17) ?
C8 C7 C6 . . 112.24(17) ?
C3 C7 H7 . . 105.7 ?
C8 C7 H7 . . 105.7 ?
C6 C7 H7 . . 105.7 ?
C9 C8 C13 . . 116.8(2) ?
C9 C8 C7 . . 121.7(2) ?
C13 C8 C7 . . 121.2(2) ?
C10 C9 C8 . . 121.5(2) ?
C10 C9 H9 . . 119.2 ?
C8 C9 H9 . . 119.2 ?
C11 C10 C9 . . 121.4(2) ?
C11 C10 H10 . . 119.3 ?
C9 C10 H10 . . 119.3 ?
C10 C11 C12 . . 117.3(2) ?
C10 C11 C14 . . 120.5(2) ?
C12 C11 C14 . . 122.2(2) ?
C13 C12 C11 . . 121.7(2) ?
C13 C12 H12 . . 119.1 ?
C11 C12 H12 . . 119.1 ?
C12 C13 C8 . . 121.2(2) ?
C12 C13 H13 . . 119.4 ?
C8 C13 H13 . . 119.4 ?
C11 C14 H14A . . 109.5 ?
C11 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C11 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
N3 C15 C16 . . 111.59(19) ?
N3 C15 C20 . . 111.02(18) ?
C16 C15 C20 . . 110.01(19) ?
N3 C15 H15 . . 108.0 ?
C16 C15 H15 . . 108.0 ?
C20 C15 H15 . . 108.0 ?
C15 C16 C17 . . 111.8(2) ?
C15 C16 H16A . . 109.3 ?
C17 C16 H16A . . 109.3 ?
C15 C16 H16B . . 109.3 ?
C17 C16 H16B . . 109.3 ?
H16A C16 H16B . . 107.9 ?
C18 C17 C16 . . 111.8(2) ?
C18 C17 H17A . . 109.3 ?
C16 C17 H17A . . 109.3 ?
C18 C17 H17B . . 109.3 ?
C16 C17 H17B . . 109.3 ?
H17A C17 H17B . . 107.9 ?
C19 C18 C17 . . 111.7(2) ?
C19 C18 H18A . . 109.3 ?
C17 C18 H18A . . 109.3 ?
C19 C18 H18B . . 109.3 ?
C17 C18 H18B . . 109.3 ?
H18A C18 H18B . . 107.9 ?
C18 C19 C20 . . 111.7(2) ?
C18 C19 H19A . . 109.3 ?
C20 C19 H19A . . 109.3 ?
C18 C19 H19B . . 109.3 ?
C20 C19 H19B . . 109.3 ?
H19A C19 H19B . . 107.9 ?
C15 C20 C19 . . 110.4(2) ?
C15 C20 H20A . . 109.6 ?
C19 C20 H20A . . 109.6 ?
C15 C20 H20B . . 109.6 ?
C19 C20 H20B . . 109.6 ?
H20A C20 H20B . . 108.1 ?
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
N1 C1 . 1.335(3) ?
N1 C4 . 1.406(3) ?
N1 H1 . 0.8600 ?
N2 C1 . 1.305(3) ?
N2 C2 . 1.380(3) ?
N3 C5 . 1.334(3) ?
N3 C15 . 1.460(3) ?
N3 H3 . 0.8600 ?
O1 C2 . 1.341(2) ?
O1 H1A . 0.8200 ?
O2 C4 . 1.230(2) ?
O3 C5 . 1.244(2) ?
C1 H1B . 0.9300 ?
C2 C3 . 1.373(3) ?
C3 C4 . 1.435(3) ?
C3 C7 . 1.519(3) ?
C5 C6 . 1.504(3) ?
C6 C7 . 1.542(3) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C8 . 1.523(3) ?
C7 H7 . 0.9800 ?
C8 C9 . 1.390(3) ?
C8 C13 . 1.396(3) ?
C9 C10 . 1.384(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.383(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.384(3) ?
C11 C14 . 1.516(3) ?
C12 C13 . 1.380(3) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 C16 . 1.522(3) ?
C15 C20 . 1.523(3) ?
C15 H15 . 0.9800 ?
C16 C17 . 1.523(3) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 C18 . 1.519(4) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 C19 . 1.515(4) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C19 C20 . 1.525(3) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
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
N1 H1 O3 1_655 0.86 1.98 2.813(3) 162 yes
O1 H1A N2 3_777 0.82 1.95 2.753(3) 168 yes
N3 H3 O2 3_776 0.86 2.19 2.992(4) 155 yes
C17 H17B Cg2 2_555 0.97 2.47 3.440(3) 177 yes
C20 H20A Cg2 3_556 0.97 2.74 3.629(3) 152 yes
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
C2 N2 C1 N1 . . . . 1.1(3) ?
C4 N1 C1 N2 . . . . -1.8(4) ?
C1 N2 C2 O1 . . . . 180.0(2) ?
C1 N2 C2 C3 . . . . -0.1(3) ?
O1 C2 C3 C4 . . . . 179.7(2) ?
N2 C2 C3 C4 . . . . -0.3(3) ?
O1 C2 C3 C7 . . . . -5.2(3) ?
N2 C2 C3 C7 . . . . 174.9(2) ?
C1 N1 C4 O2 . . . . -178.3(2) ?
C1 N1 C4 C3 . . . . 1.3(3) ?
C2 C3 C4 O2 . . . . 179.2(2) ?
C7 C3 C4 O2 . . . . 4.0(4) ?
C2 C3 C4 N1 . . . . -0.3(3) ?
C7 C3 C4 N1 . . . . -175.56(18) ?
C15 N3 C5 O3 . . . . -4.8(3) ?
C15 N3 C5 C6 . . . . 174.2(2) ?
O3 C5 C6 C7 . . . . 66.6(3) ?
N3 C5 C6 C7 . . . . -112.4(2) ?
C2 C3 C7 C8 . . . . 117.4(2) ?
C4 C3 C7 C8 . . . . -67.5(3) ?
C2 C3 C7 C6 . . . . -113.1(2) ?
C4 C3 C7 C6 . . . . 62.0(3) ?
C5 C6 C7 C3 . . . . 44.5(2) ?
C5 C6 C7 C8 . . . . 175.24(18) ?
C3 C7 C8 C9 . . . . 153.35(19) ?
C6 C7 C8 C9 . . . . 24.0(3) ?
C3 C7 C8 C13 . . . . -33.2(3) ?
C6 C7 C8 C13 . . . . -162.62(19) ?
C13 C8 C9 C10 . . . . -4.0(3) ?
C7 C8 C9 C10 . . . . 169.7(2) ?
C8 C9 C10 C11 . . . . 1.0(3) ?
C9 C10 C11 C12 . . . . 2.5(3) ?
C9 C10 C11 C14 . . . . -176.1(2) ?
C10 C11 C12 C13 . . . . -3.1(3) ?
C14 C11 C12 C13 . . . . 175.5(2) ?
C11 C12 C13 C8 . . . . 0.1(3) ?
C9 C8 C13 C12 . . . . 3.4(3) ?
C7 C8 C13 C12 . . . . -170.3(2) ?
C5 N3 C15 C16 . . . . -94.9(3) ?
C5 N3 C15 C20 . . . . 142.0(2) ?
N3 C15 C16 C17 . . . . 179.60(18) ?
C20 C15 C16 C17 . . . . -56.7(3) ?
C15 C16 C17 C18 . . . . 54.0(3) ?
C16 C17 C18 C19 . . . . -52.2(3) ?
C17 C18 C19 C20 . . . . 54.0(3) ?
N3 C15 C20 C19 . . . . -178.2(2) ?
C16 C15 C20 C19 . . . . 57.8(3) ?
C18 C19 C20 C15 . . . . -57.0(3) ?
