#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/09/2210912.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_2210912
loop_
_publ_author_name
'Shao-Fa Sun'
_publ_section_title
;
 4-Benzylidene-2-(isopropylamino)-1-phenylimidazolin-5(4H)-one
;
_journal_coeditor_code           BX2029
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5130
_journal_page_last               o5131
_journal_paper_doi               10.1107/S1600536806042541
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C19 H19 N3 O'
_chemical_formula_moiety         'C19 H19 N3 O'
_chemical_formula_sum            'C19 H19 N3 O'
_chemical_formula_weight         305.37
_chemical_melting_point          397
_chemical_name_systematic
;
4-Benzylidene-2-(isopropylamino)-1-phenyl-imidazolin-5(4H)-one
 ?
;
_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                 94.880(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1186(15)
_cell_length_b                   10.8172(13)
_cell_length_c                   12.8606(16)
_cell_measurement_reflns_used    3899
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      27.28
_cell_measurement_theta_min      2.41
_cell_volume                     1679.8(4)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9888
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3792
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0493
_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)+(0.0778P)²+0.0795P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1484
_reflns_number_gt                2818
_reflns_number_total             3792
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bx2029.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2210912
_cod_database_fobs_code          2210912
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
C C1 0.03441(14) 0.28283(15) 0.81601(15) 0.0745(5) Uani d . 1
H H1 -0.0070 0.2128 0.7972 0.089 Uiso calc R 1
C C2 -0.01716(17) 0.38882(19) 0.84717(16) 0.0896(6) Uani d . 1
H H2 -0.0936 0.3897 0.8503 0.107 Uiso calc R 1
C C3 0.04344(19) 0.49204(17) 0.87340(13) 0.0836(6) Uani d . 1
H H3 0.0083 0.5636 0.8934 0.100 Uiso calc R 1
C C4 0.1555(2) 0.49031(16) 0.87028(15) 0.0877(6) Uani d . 1
H H4 0.1966 0.5609 0.8882 0.105 Uiso calc R 1
C C5 0.20847(15) 0.38490(14) 0.84090(13) 0.0719(4) Uani d . 1
H H5 0.2851 0.3836 0.8399 0.086 Uiso calc R 1
C C6 0.14701(12) 0.28188(11) 0.81311(10) 0.0511(3) Uani d . 1
C C7 0.23724(12) 0.15769(12) 0.67941(11) 0.0544(3) Uani d . 1
C C8 0.28817(11) 0.03249(12) 0.68559(10) 0.0501(3) Uani d . 1
C C9 0.22442(10) 0.06460(11) 0.83421(10) 0.0488(3) Uani d . 1
C C10 0.34003(11) -0.01458(13) 0.60627(11) 0.0554(3) Uani d . 1
H H10 0.3377 0.0343 0.5466 0.066 Uiso calc R 1
C C11 0.39925(11) -0.13090(13) 0.60019(11) 0.0568(4) Uani d . 1
C C12 0.41650(14) -0.21285(15) 0.68313(14) 0.0716(4) Uani d . 1
H H12 0.3885 -0.1946 0.7465 0.086 Uiso calc R 1
C C13 0.47498(16) -0.32140(18) 0.67250(16) 0.0869(6) Uani d . 1
H H13 0.4857 -0.3756 0.7286 0.104 Uiso calc R 1
C C14 0.51727(14) -0.34963(19) 0.57949(17) 0.0844(6) Uani d . 1
H H14 0.5564 -0.4227 0.5728 0.101 Uiso calc R 1
C C15 0.50171(15) -0.27007(18) 0.49670(17) 0.0820(5) Uani d . 1
H H15 0.5303 -0.2890 0.4338 0.098 Uiso calc R 1
C C16 0.44358(13) -0.16183(16) 0.50681(13) 0.0692(4) Uani d . 1
H H16 0.4336 -0.1082 0.4503 0.083 Uiso calc R 1
C C17 0.21249(14) -0.06243(12) 0.99001(12) 0.0615(4) Uani d . 1
H H17 0.2878 -0.0914 0.9816 0.074 Uiso calc R 1
C C18 0.2032(2) -0.03674(17) 1.10370(14) 0.0931(6) Uani d . 1
H H18A 0.2593 0.0214 1.1284 0.140 Uiso calc R 1
H H18B 0.2130 -0.1123 1.1426 0.140 Uiso calc R 1
H H18C 0.1314 -0.0029 1.1128 0.140 Uiso calc R 1
C C19 0.1325(2) -0.16079(18) 0.94959(16) 0.0991(7) Uani d . 1
H H19A 0.0582 -0.1339 0.9573 0.149 Uiso calc R 1
H H19B 0.1470 -0.2356 0.9885 0.149 Uiso calc R 1
H H19C 0.1413 -0.1757 0.8772 0.149 Uiso calc R 1
N N1 0.20119(9) 0.17406(10) 0.77834(9) 0.0529(3) Uani d . 1
N N2 0.27473(9) -0.01924(10) 0.78325(9) 0.0515(3) Uani d . 1
N N3 0.19461(11) 0.05313(10) 0.93133(9) 0.0586(3) Uani d D 1
H H3A 0.1738(13) 0.1174(11) 0.9644(12) 0.070 Uiso d D 1
O O1 0.22715(11) 0.23147(10) 0.60850(9) 0.0771(4) Uani 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
C6 C1 C2 119.41(17)
C6 C1 H1 120.3
C2 C1 H1 120.3
C3 C2 C1 120.28(18)
C3 C2 H2 119.9
C1 C2 H2 119.9
C4 C3 C2 119.94(16)
C4 C3 H3 120.0
C2 C3 H3 120.0
C3 C4 C5 120.58(18)
C3 C4 H4 119.7
C5 C4 H4 119.7
C6 C5 C4 119.27(17)
C6 C5 H5 120.4
C4 C5 H5 120.4
C1 C6 C5 120.52(13)
C1 C6 N1 120.04(13)
C5 C6 N1 119.42(13)
O1 C7 N1 125.85(12)
O1 C7 C8 130.96(13)
N1 C7 C8 103.19(11)
C10 C8 N2 128.96(13)
C10 C8 C7 121.56(13)
N2 C8 C7 109.46(11)
N2 C9 N3 125.61(12)
N2 C9 N1 114.40(11)
N3 C9 N1 119.98(11)
C8 C10 C11 129.34(14)
C8 C10 H10 115.3
C11 C10 H10 115.3
C12 C11 C16 117.61(14)
C12 C11 C10 123.62(13)
C16 C11 C10 118.75(14)
C13 C12 C11 120.69(16)
C13 C12 H12 119.7
C11 C12 H12 119.7
C14 C13 C12 120.40(19)
C14 C13 H13 119.8
C12 C13 H13 119.8
C15 C14 C13 119.99(16)
C15 C14 H14 120.0
C13 C14 H14 120.0
C14 C15 C16 119.87(17)
C14 C15 H15 120.1
C16 C15 H15 120.1
C15 C16 C11 121.43(17)
C15 C16 H16 119.3
C11 C16 H16 119.3
N3 C17 C19 111.29(14)
N3 C17 C18 108.85(12)
C19 C17 C18 111.62(15)
N3 C17 H17 108.3
C19 C17 H17 108.3
C18 C17 H17 108.3
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C17 C19 H19A 109.5
C17 C19 H19B 109.5
H19A C19 H19B 109.5
C17 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C7 N1 C9 107.24(10)
C7 N1 C6 125.35(10)
C9 N1 C6 127.37(10)
C9 N2 C8 105.62(11)
C9 N3 C17 121.37(11)
C9 N3 H3A 120.0(11)
C17 N3 H3A 118.0(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.368(2)
C1 C2 1.381(2)
C1 H1 0.9300
C2 C3 1.363(3)
C2 H2 0.9300
C3 C4 1.362(3)
C3 H3 0.9300
C4 C5 1.377(2)
C4 H4 0.9300
C5 C6 1.371(2)
C5 H5 0.9300
C6 N1 1.4288(16)
C7 O1 1.2102(16)
C7 N1 1.3913(17)
C7 C8 1.4876(19)
C8 C10 1.3431(19)
C8 N2 1.3970(17)
C9 N2 1.3007(16)
C9 N3 1.3352(17)
C9 N1 1.4010(17)
C10 C11 1.454(2)
C10 H10 0.9300
C11 C12 1.389(2)
C11 C16 1.397(2)
C12 C13 1.384(2)
C12 H12 0.9300
C13 C14 1.375(3)
C13 H13 0.9300
C14 C15 1.370(3)
C14 H14 0.9300
C15 C16 1.378(2)
C15 H15 0.9300
C16 H16 0.9300
C17 N3 1.4667(18)
C17 C19 1.502(3)
C17 C18 1.502(2)
C17 H17 0.9800
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
N3 H3A 0.863(9)
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
C12 H12 N2 . 0.93 2.42 3.0614(19) 126.5 yes
N3 H3A O1 4_566 0.863(9) 2.515(12) 3.2593(16) 145.0(14) 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
C6 C1 C2 C3 0.9(3)
C1 C2 C3 C4 -0.9(3)
C2 C3 C4 C5 -0.1(3)
C3 C4 C5 C6 1.0(3)
C2 C1 C6 C5 0.1(2)
C2 C1 C6 N1 -178.30(15)
C4 C5 C6 C1 -1.0(2)
C4 C5 C6 N1 177.36(15)
O1 C7 C8 C10 4.5(2)
N1 C7 C8 C10 -175.49(13)
O1 C7 C8 N2 -177.14(16)
N1 C7 C8 N2 2.92(14)
N2 C8 C10 C11 -1.8(2)
C7 C8 C10 C11 176.31(13)
C8 C10 C11 C12 -3.5(2)
C8 C10 C11 C16 177.81(14)
C16 C11 C12 C13 -0.4(2)
C10 C11 C12 C13 -179.11(15)
C11 C12 C13 C14 0.2(3)
C12 C13 C14 C15 0.0(3)
C13 C14 C15 C16 0.0(3)
C14 C15 C16 C11 -0.2(3)
C12 C11 C16 C15 0.5(2)
C10 C11 C16 C15 179.20(15)
O1 C7 N1 C9 177.19(15)
C8 C7 N1 C9 -2.86(14)
O1 C7 N1 C6 -0.7(2)
C8 C7 N1 C6 179.24(12)
N2 C9 N1 C7 2.08(16)
N3 C9 N1 C7 -177.63(12)
N2 C9 N1 C6 179.92(12)
N3 C9 N1 C6 0.2(2)
C1 C6 N1 C7 100.42(17)
C5 C6 N1 C7 -77.95(18)
C1 C6 N1 C9 -77.06(19)
C5 C6 N1 C9 104.57(17)
N3 C9 N2 C8 179.55(13)
N1 C9 N2 C8 -0.13(15)
C10 C8 N2 C9 176.50(14)
C7 C8 N2 C9 -1.75(14)
N2 C9 N3 C17 -2.9(2)
N1 C9 N3 C17 176.80(13)
C19 C17 N3 C9 -73.26(19)
C18 C17 N3 C9 163.31(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655085
