#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/21/2222157.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_2222157
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Yeap, Chin Sing'
'Sujith, K. V.'
'Kalluraya, B.'
_publ_section_title
;Ethyl
 4-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
;
_journal_coeditor_code           TK2442
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1229
_journal_paper_doi               10.1107/S1600536809016365
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H19 Cl N4 O3'
_chemical_formula_moiety         'C18 H19 Cl N4 O3'
_chemical_formula_sum            'C18 H19 Cl N4 O3'
_chemical_formula_weight         374.82
_chemical_name_systematic
;
Ethyl 4-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-methyl-2-oxo-
1,2,3,4-tetrahydropyrimidine-5-carboxylate
;
_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                93.3940(10)
_cell_angle_beta                 99.3790(10)
_cell_angle_gamma                90.2030(10)
_cell_formula_units_Z            2
_cell_length_a                   7.9083(2)
_cell_length_b                   10.2600(2)
_cell_length_c                   10.9075(3)
_cell_measurement_reflns_used    9944
_cell_measurement_temperature    110
_cell_measurement_theta_max      35.8
_cell_measurement_theta_min      2.6
_cell_volume                     871.58(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      110
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
;
Bruker SMART APEXII 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  0.026
_diffrn_reflns_av_sigmaI/netI    0.026
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18224
_diffrn_reflns_theta_full        30.0
_diffrn_reflns_theta_max         30.0
_diffrn_reflns_theta_min         1.9
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.48
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         5048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.044
_refine_ls_R_factor_gt           0.036
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0515P)²+0.3283P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.093
_refine_ls_wR_factor_ref         0.099
_reflns_number_gt                4355
_reflns_number_total             5048
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2442.cif
_cod_data_source_block           I
_cod_database_code               2222157
_cod_database_fobs_code          2222157
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cl Cl1 0.16502(4) 0.27288(3) 0.28593(3) 0.01867(8) Uani d . 1 . .
O O1 0.09492(11) 0.60474(9) 0.13406(8) 0.01980(18) Uani d . 1 . .
O O2 0.64558(11) 0.20298(9) 0.00629(8) 0.02096(19) Uani d . 1 . .
O O3 0.77714(11) 0.29869(9) 0.18745(8) 0.02079(19) Uani d . 1 . .
N N1 0.40982(13) 0.25693(10) 0.48878(9) 0.01486(19) Uani d . 1 . .
N N2 0.57439(13) 0.29637(10) 0.53670(9) 0.01546(19) Uani d . 1 . .
N N3 0.36526(13) 0.54573(10) 0.21278(9) 0.01470(19) Uani d . 1 . .
N N4 0.21476(13) 0.43462(10) 0.03761(9) 0.0162(2) Uani d . 1 . .
C C1 0.41198(18) 0.06888(12) 0.61334(11) 0.0202(2) Uani d . 1 . .
H H1A 0.5286 0.0600 0.6116 0.024 Uiso calc R 1 . .
C C2 0.3256(2) -0.01924(13) 0.67359(12) 0.0253(3) Uani d . 1 . .
H H2A 0.3844 -0.0884 0.7115 0.030 Uiso calc R 1 . .
C C3 0.1527(2) -0.00483(14) 0.67768(12) 0.0265(3) Uani d . 1 . .
H H3A 0.0951 -0.0654 0.7165 0.032 Uiso calc R 1 . .
C C4 0.06518(18) 0.09986(14) 0.62404(12) 0.0254(3) Uani d . 1 . .
H H4A -0.0503 0.1106 0.6289 0.030 Uiso calc R 1 . .
C C5 0.14923(16) 0.18874(13) 0.56301(11) 0.0202(2) Uani d . 1 . .
H H5A 0.0910 0.2594 0.5276 0.024 Uiso calc R 1 . .
C C6 0.32146(16) 0.17084(11) 0.55550(10) 0.0161(2) Uani d . 1 . .
C C7 0.36219(14) 0.30274(11) 0.37349(10) 0.0143(2) Uani d . 1 . .
C C8 0.49610(14) 0.37464(11) 0.34481(10) 0.0132(2) Uani d . 1 . .
C C9 0.62520(14) 0.36737(11) 0.45051(10) 0.0144(2) Uani d . 1 . .
C C10 0.50187(14) 0.44856(11) 0.22960(10) 0.0135(2) Uani d . 1 . .
H H10A 0.6117 0.4960 0.2419 0.016 Uiso calc R 1 . .
C C11 0.21883(15) 0.53209(11) 0.13033(10) 0.0150(2) Uani d . 1 . .
C C12 0.35013(15) 0.35289(11) 0.02438(10) 0.0146(2) Uani d . 1 . .
C C13 0.49312(14) 0.35937(11) 0.11231(10) 0.0140(2) Uani d . 1 . .
C C14 0.65113(15) 0.28596(11) 0.10717(11) 0.0155(2) Uani d . 1 . .
C C15 0.80143(17) 0.13146(13) -0.00265(12) 0.0223(3) Uani d . 1 . .
H H15A 0.8243 0.0716 0.0635 0.027 Uiso calc R 1 . .
H H15B 0.8983 0.1912 0.0039 0.027 Uiso calc R 1 . .
C C16 0.7726(2) 0.05757(18) -0.12749(15) 0.0387(4) Uani d . 1 . .
H H16A 0.8746 0.0112 -0.1390 0.058 Uiso calc R 1 . .
H H16B 0.7456 0.1177 -0.1918 0.058 Uiso calc R 1 . .
H H16C 0.6793 -0.0034 -0.1314 0.058 Uiso calc R 1 . .
C C17 0.31577(17) 0.26349(13) -0.09159(12) 0.0201(2) Uani d . 1 . .
H H17A 0.207(3) 0.2792(18) -0.1382(18) 0.034(5) Uiso d . 1 . .
H H17B 0.316(3) 0.175(2) -0.0718(18) 0.038(5) Uiso d . 1 . .
H H17C 0.398(2) 0.2794(18) -0.1447(17) 0.034(5) Uiso d . 1 . .
C C18 0.79965(15) 0.42889(12) 0.47221(12) 0.0187(2) Uani d . 1 . .
H H18A 0.8530 0.4188 0.5566 0.028 Uiso calc R 1 . .
H H18B 0.7902 0.5201 0.4575 0.028 Uiso calc R 1 . .
H H18C 0.8679 0.3874 0.4164 0.028 Uiso calc R 1 . .
H H1N3 0.367(2) 0.6038(15) 0.2734(15) 0.016(4) Uiso d . 1 . .
H H1N4 0.120(2) 0.4247(17) -0.0173(17) 0.026(4) 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'
Cl Cl 0.1484 0.1585 '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
C14 O2 C15 . . 115.79(9) ?
C7 N1 N2 . . 110.16(9) ?
C7 N1 C6 . . 130.02(10) ?
N2 N1 C6 . . 119.60(9) ?
C9 N2 N1 . . 105.46(9) ?
C11 N3 C10 . . 125.12(9) ?
C11 N3 H1N3 . . 117.1(10) ?
C10 N3 H1N3 . . 115.4(10) ?
C11 N4 C12 . . 124.24(10) ?
C11 N4 H1N4 . . 117.5(11) ?
C12 N4 H1N4 . . 118.3(11) ?
C2 C1 C6 . . 119.05(12) ?
C2 C1 H1A . . 120.5 ?
C6 C1 H1A . . 120.5 ?
C3 C2 C1 . . 120.45(12) ?
C3 C2 H2A . . 119.8 ?
C1 C2 H2A . . 119.8 ?
C2 C3 C4 . . 120.08(13) ?
C2 C3 H3A . . 120.0 ?
C4 C3 H3A . . 120.0 ?
C3 C4 C5 . . 120.28(13) ?
C3 C4 H4A . . 119.9 ?
C5 C4 H4A . . 119.9 ?
C4 C5 C6 . . 119.22(12) ?
C4 C5 H5A . . 120.4 ?
C6 C5 H5A . . 120.4 ?
C5 C6 C1 . . 120.82(12) ?
C5 C6 N1 . . 120.71(11) ?
C1 C6 N1 . . 118.47(11) ?
N1 C7 C8 . . 108.70(10) ?
N1 C7 Cl1 . . 123.11(9) ?
C8 C7 Cl1 . . 128.18(9) ?
C7 C8 C9 . . 103.79(10) ?
C7 C8 C10 . . 128.17(10) ?
C9 C8 C10 . . 128.00(10) ?
N2 C9 C8 . . 111.88(10) ?
N2 C9 C18 . . 120.43(10) ?
C8 C9 C18 . . 127.69(11) ?
N3 C10 C8 . . 111.17(9) ?
N3 C10 C13 . . 110.10(9) ?
C8 C10 C13 . . 112.92(9) ?
N3 C10 H10A . . 107.5 ?
C8 C10 H10A . . 107.5 ?
C13 C10 H10A . . 107.5 ?
O1 C11 N3 . . 122.70(10) ?
O1 C11 N4 . . 120.82(10) ?
N3 C11 N4 . . 116.45(10) ?
C13 C12 N4 . . 119.61(10) ?
C13 C12 C17 . . 127.57(10) ?
N4 C12 C17 . . 112.82(10) ?
C12 C13 C14 . . 125.95(10) ?
C12 C13 C10 . . 120.88(10) ?
C14 C13 C10 . . 113.16(9) ?
O3 C14 O2 . . 122.46(11) ?
O3 C14 C13 . . 122.92(11) ?
O2 C14 C13 . . 114.63(10) ?
O2 C15 C16 . . 106.46(10) ?
O2 C15 H15A . . 110.4 ?
C16 C15 H15A . . 110.4 ?
O2 C15 H15B . . 110.4 ?
C16 C15 H15B . . 110.4 ?
H15A C15 H15B . . 108.6 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C12 C17 H17A . . 111.0(11) ?
C12 C17 H17B . . 111.1(12) ?
H17A C17 H17B . . 106.9(16) ?
C12 C17 H17C . . 110.3(11) ?
H17A C17 H17C . . 106.4(16) ?
H17B C17 H17C . . 111.0(17) ?
C9 C18 H18A . . 109.5 ?
C9 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C9 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
Cl1 C7 . 1.7070(12) ?
O1 C11 . 1.2378(14) ?
O2 C14 . 1.3456(14) ?
O2 C15 . 1.4505(14) ?
O3 C14 . 1.2157(14) ?
N1 C7 . 1.3641(14) ?
N1 N2 . 1.3712(13) ?
N1 C6 . 1.4268(15) ?
N2 C9 . 1.3334(15) ?
N3 C11 . 1.3468(14) ?
N3 C10 . 1.4695(14) ?
N3 H1N3 . 0.862(16) ?
N4 C11 . 1.3760(15) ?
N4 C12 . 1.3828(14) ?
N4 H1N4 . 0.883(18) ?
C1 C2 . 1.3886(18) ?
C1 C6 . 1.3932(17) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.383(2) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.387(2) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.3887(18) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.3899(17) ?
C5 H5A . 0.9300 ?
C7 C8 . 1.3760(16) ?
C8 C9 . 1.4158(15) ?
C8 C10 . 1.5125(15) ?
C9 C18 . 1.4924(16) ?
C10 C13 . 1.5202(15) ?
C10 H10A . 0.9800 ?
C12 C13 . 1.3570(15) ?
C12 C17 . 1.5047(16) ?
C13 C14 . 1.4685(15) ?
C15 C16 . 1.5020(19) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 H17A . 0.95(2) ?
C17 H17B . 0.95(2) ?
C17 H17C . 0.956(19) ?
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
N3 H1N3 N2 2_666 0.863(16) 2.233(16) 3.0601(14) 160.7(14) y
N4 H1N4 O1 2_565 0.882(17) 1.960(17) 2.8418(13) 176.8(17) y
C18 H18C O3 . 0.96 2.59 3.2850(15) 129 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
C7 N1 N2 C9 . . . . 0.68(12) ?
C6 N1 N2 C9 . . . . 175.80(10) ?
C6 C1 C2 C3 . . . . -0.95(19) ?
C1 C2 C3 C4 . . . . -1.6(2) ?
C2 C3 C4 C5 . . . . 1.8(2) ?
C3 C4 C5 C6 . . . . 0.54(19) ?
C4 C5 C6 C1 . . . . -3.09(18) ?
C4 C5 C6 N1 . . . . 177.20(11) ?
C2 C1 C6 C5 . . . . 3.29(18) ?
C2 C1 C6 N1 . . . . -176.99(11) ?
C7 N1 C6 C5 . . . . -46.54(17) ?
N2 N1 C6 C5 . . . . 139.45(11) ?
C7 N1 C6 C1 . . . . 133.75(13) ?
N2 N1 C6 C1 . . . . -40.27(15) ?
N2 N1 C7 C8 . . . . -0.59(13) ?
C6 N1 C7 C8 . . . . -175.05(11) ?
N2 N1 C7 Cl1 . . . . -179.88(8) ?
C6 N1 C7 Cl1 . . . . 5.67(17) ?
N1 C7 C8 C9 . . . . 0.25(12) ?
Cl1 C7 C8 C9 . . . . 179.49(9) ?
N1 C7 C8 C10 . . . . -177.62(10) ?
Cl1 C7 C8 C10 . . . . 1.62(18) ?
N1 N2 C9 C8 . . . . -0.52(12) ?
N1 N2 C9 C18 . . . . 178.99(10) ?
C7 C8 C9 N2 . . . . 0.18(13) ?
C10 C8 C9 N2 . . . . 178.06(10) ?
C7 C8 C9 C18 . . . . -179.29(11) ?
C10 C8 C9 C18 . . . . -1.41(19) ?
C11 N3 C10 C8 . . . . -103.04(12) ?
C11 N3 C10 C13 . . . . 22.87(15) ?
C7 C8 C10 N3 . . . . 57.33(15) ?
C9 C8 C10 N3 . . . . -120.05(12) ?
C7 C8 C10 C13 . . . . -67.00(15) ?
C9 C8 C10 C13 . . . . 115.62(12) ?
C10 N3 C11 O1 . . . . 166.80(11) ?
C10 N3 C11 N4 . . . . -15.22(16) ?
C12 N4 C11 O1 . . . . 177.43(11) ?
C12 N4 C11 N3 . . . . -0.59(17) ?
C11 N4 C12 C13 . . . . 5.61(18) ?
C11 N4 C12 C17 . . . . -174.82(11) ?
N4 C12 C13 C14 . . . . -175.52(11) ?
C17 C12 C13 C14 . . . . 5.0(2) ?
N4 C12 C13 C10 . . . . 4.26(17) ?
C17 C12 C13 C10 . . . . -175.23(11) ?
N3 C10 C13 C12 . . . . -16.61(15) ?
C8 C10 C13 C12 . . . . 108.30(12) ?
N3 C10 C13 C14 . . . . 163.20(9) ?
C8 C10 C13 C14 . . . . -71.89(12) ?
C15 O2 C14 O3 . . . . -1.48(17) ?
C15 O2 C14 C13 . . . . 178.58(10) ?
C12 C13 C14 O3 . . . . 177.86(12) ?
C10 C13 C14 O3 . . . . -1.93(17) ?
C12 C13 C14 O2 . . . . -2.20(17) ?
C10 C13 C14 O2 . . . . 178.00(10) ?
C14 O2 C15 C16 . . . . -173.84(12) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2271371
