#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/83/2218381.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_2218381
loop_
_publ_author_name
'Dai, Wei'
'Fu, Da-Wei'
_publ_section_title
;(+-)-5-Ethyl-2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic
 acid
;
_journal_coeditor_code           DN2325
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o971
_journal_paper_doi               10.1107/S1600536808007411
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C15 H19 N3 O3'
_chemical_formula_moiety         'C15 H19 N3 O3'
_chemical_formula_sum            'C15 H19 N3 O3'
_chemical_formula_weight         289.33
_chemical_name_systematic
;
(+-)-5-Ethyl-2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-
yl)nicotinic acid
;
_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                 100.213(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.6916(15)
_cell_length_b                   16.0748(17)
_cell_length_c                   7.3801(8)
_cell_measurement_reflns_used    2685
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4798
_cell_measurement_theta_min      3.0266
_cell_volume                     1481.8(3)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia,
1997) and
PLATON (Spek, 2003)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Mercury2 (2x2 bin mode)'
_diffrn_measurement_method       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  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15016
_diffrn_reflns_theta_full        27.36
_diffrn_reflns_theta_max         27.36
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.199
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3357
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0509
_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)+(0.0611P)²+0.3777P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1360
_reflns_number_gt                2413
_reflns_number_total             3357
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2325.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2218381
_cod_database_fobs_code          2218381
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
N N1 0.56210(12) 0.92867(8) 0.3216(2) 0.0442(4) Uani d . 1
N N2 0.31126(10) 0.86524(8) 0.06785(19) 0.0358(3) Uani d . 1
N N3 0.38168(11) 0.99041(8) 0.1425(2) 0.0419(4) Uani d . 1
H H3 0.4293 1.0259 0.1901 0.050 Uiso calc R 1
O O1 0.36104(10) 0.71477(7) 0.09236(19) 0.0484(4) Uani d . 1
H H1 0.3450 0.7642 0.0817 0.073 Uiso calc R 1
O O2 0.48765(11) 0.63866(7) 0.2486(2) 0.0590(4) Uani d . 1
O O3 0.24362(11) 1.07812(8) 0.0169(2) 0.0626(4) Uani d . 1
C C1 0.65661(14) 0.90689(11) 0.4182(3) 0.0465(5) Uani d . 1
H H1A 0.7023 0.9491 0.4702 0.056 Uiso calc R 1
C C2 0.69167(13) 0.82543(11) 0.4465(2) 0.0385(4) Uani d . 1
C C3 0.62079(13) 0.76450(10) 0.3712(2) 0.0354(4) Uani d . 1
H H3A 0.6409 0.7090 0.3883 0.042 Uiso calc R 1
C C4 0.51990(12) 0.78314(9) 0.2704(2) 0.0304(3) Uani d . 1
C C5 0.49432(12) 0.86849(9) 0.2486(2) 0.0328(4) Uani d . 1
C C6 0.39348(13) 0.90513(9) 0.1502(2) 0.0337(4) Uani d . 1
C C7 0.80073(15) 0.80620(13) 0.5550(3) 0.0508(5) Uani d . 1
H H7A 0.8117 0.7465 0.5559 0.061 Uiso calc R 1
H H7B 0.8035 0.8240 0.6813 0.061 Uiso calc R 1
C C8 0.89069(16) 0.84795(14) 0.4789(3) 0.0624(6) Uani d . 1
H H8A 0.8871 0.8321 0.3525 0.094 Uiso calc R 1
H H8B 0.9583 0.8309 0.5492 0.094 Uiso calc R 1
H H8C 0.8837 0.9072 0.4868 0.094 Uiso calc R 1
C C9 0.45278(13) 0.70696(10) 0.2013(2) 0.0366(4) Uani d . 1
C C10 0.28196(14) 1.00956(10) 0.0468(3) 0.0429(4) Uani d . 1
C C11 0.22886(13) 0.92565(10) -0.0124(2) 0.0373(4) Uani d . 1
C C12 0.12537(15) 0.91484(12) 0.0676(3) 0.0492(5) Uani d . 1
H H12 0.0754 0.9583 0.0133 0.059 Uiso calc R 1
C C13 0.0711(2) 0.83164(17) 0.0180(4) 0.0788(8) Uani d . 1
H H13A 0.1161 0.7876 0.0757 0.118 Uiso calc R 1
H H13B 0.0592 0.8244 -0.1131 0.118 Uiso calc R 1
H H13C 0.0038 0.8303 0.0602 0.118 Uiso calc R 1
C C14 0.1441(2) 0.92685(19) 0.2749(3) 0.0857(9) Uani d . 1
H H14A 0.0772 0.9224 0.3177 0.128 Uiso calc R 1
H H14B 0.1745 0.9809 0.3050 0.128 Uiso calc R 1
H H14C 0.1924 0.8849 0.3329 0.128 Uiso calc R 1
C C15 0.21042(17) 0.91982(12) -0.2218(3) 0.0527(5) Uani d . 1
H H15A 0.2770 0.9283 -0.2638 0.079 Uiso calc R 1
H H15B 0.1600 0.9617 -0.2737 0.079 Uiso calc R 1
H H15C 0.1827 0.8658 -0.2596 0.079 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
C1 N1 C5 118.60(14)
C6 N2 C11 108.73(13)
C10 N3 C6 109.15(14)
C10 N3 H3 125.4
C6 N3 H3 125.4
C9 O1 H1 109.5
N1 C1 C2 124.36(16)
N1 C1 H1A 117.8
C2 C1 H1A 117.8
C3 C2 C1 116.18(15)
C3 C2 C7 122.83(16)
C1 C2 C7 120.99(16)
C2 C3 C4 122.28(15)
C2 C3 H3A 118.9
C4 C3 H3A 118.9
C3 C4 C5 116.13(14)
C3 C4 C9 114.27(14)
C5 C4 C9 129.60(14)
N1 C5 C4 122.43(15)
N1 C5 C6 110.34(13)
C4 C5 C6 127.23(14)
N2 C6 N3 113.84(14)
N2 C6 C5 126.50(14)
N3 C6 C5 119.66(14)
C2 C7 C8 113.25(16)
C2 C7 H7A 108.9
C8 C7 H7A 108.9
C2 C7 H7B 108.9
C8 C7 H7B 108.9
H7A C7 H7B 107.7
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O2 C9 O1 120.50(15)
O2 C9 C4 118.47(15)
O1 C9 C4 121.02(13)
O3 C10 N3 127.14(17)
O3 C10 C11 127.32(16)
N3 C10 C11 105.54(13)
N2 C11 C15 109.74(14)
N2 C11 C10 102.72(13)
C15 C11 C10 108.85(15)
N2 C11 C12 111.34(14)
C15 C11 C12 113.15(15)
C10 C11 C12 110.51(14)
C14 C12 C13 109.8(2)
C14 C12 C11 112.33(16)
C13 C12 C11 112.79(17)
C14 C12 H12 107.2
C13 C12 H12 107.2
C11 C12 H12 107.2
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C12 C14 H14A 109.5
C12 C14 H14B 109.5
H14A C14 H14B 109.5
C12 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C11 C15 H15A 109.5
C11 C15 H15B 109.5
H15A C15 H15B 109.5
C11 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.329(2)
N1 C5 1.342(2)
N2 C6 1.282(2)
N2 C11 1.472(2)
N3 C10 1.370(2)
N3 C6 1.379(2)
N3 H3 0.8600
O1 C9 1.298(2)
O1 H1 0.8200
O2 C9 1.2118(19)
O3 C10 1.209(2)
C1 C2 1.387(2)
C1 H1A 0.9300
C2 C3 1.378(2)
C2 C7 1.503(2)
C3 C4 1.395(2)
C3 H3A 0.9300
C4 C5 1.412(2)
C4 C9 1.527(2)
C5 C6 1.477(2)
C7 C8 1.515(3)
C7 H7A 0.9700
C7 H7B 0.9700
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C10 C11 1.536(2)
C11 C15 1.524(3)
C11 C12 1.543(3)
C12 C14 1.518(3)
C12 C13 1.519(3)
C12 H12 0.9800
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 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
O1 H1 N2 . 0.82 1.68 2.4984(18) 177.9
N3 H3 O2 2_655 0.86 2.10 2.9330(19) 161.5
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 49447
