#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/30/2223099.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_2223099
loop_
_publ_author_name
'Murtaza, Ghulam'
'Ebihara, Masahiro'
'Said, Muhammad'
'Khawar Rauf, M.'
'Anwar, Saeed'
_publ_section_title
;
 2-Benzoyl-1-(2,4-dichlorophenyl)-3-phenylguanidine
;
_journal_coeditor_code           HG2555
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2297
_journal_page_last               o2298
_journal_paper_doi               10.1107/S160053680903387X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H15 Cl2 N3 O'
_chemical_formula_moiety         'C20 H15 Cl2 N3 O'
_chemical_formula_sum            'C20 H15 Cl2 N3 O'
_chemical_formula_weight         384.25
_chemical_name_systematic
;
2-Benzoyl-1-(2,4-dichlorophenyl)-3-phenylguanidine
;
_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                 124.072(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.461(6)
_cell_length_b                   6.663(2)
_cell_length_c                   19.388(6)
_cell_measurement_reflns_used    5226
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1761.4(10)
_computing_cell_refinement
'CrystalClear (Molecular Structure Corporation & Rigaku, 2001)'
_computing_data_collection
'CrystalClear (Molecular Structure Corporation & Rigaku, 2001)'
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation & Rigaku, 2004)'
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and
TEXSAN (Molecular Structure Corporation & Rigaku, 2004)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 14.62
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13586
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.31
_exptl_absorpt_coefficient_mu    0.383
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.271
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0423
_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)+(0.0364P)²+1.087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.0992
_reflns_number_gt                3768
_reflns_number_total             4023
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2555.cif
_cod_data_source_block           I
_cod_original_cell_volume        1761.0(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2223099
_cod_database_fobs_code          2223099
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
C C1 0.16683(11) 0.5401(2) 0.00837(10) 0.0159(3) Uani d . 1 . .
N N1 0.23055(9) 0.3930(2) 0.05737(8) 0.0168(3) Uani d . 1 . .
N N2 0.27838(10) 0.1383(2) 0.15357(9) 0.0190(3) Uani d . 1 . .
H H2 0.2660(14) 0.070(3) 0.1846(13) 0.023 Uiso d . 1 . .
N N3 0.12213(10) 0.2596(2) 0.09071(9) 0.0176(3) Uani d . 1 . .
H H3 0.0802(15) 0.344(3) 0.0586(13) 0.021 Uiso d . 1 . .
C C2 0.20779(11) 0.2689(2) 0.09780(10) 0.0159(3) Uani d . 1 . .
O O1 0.08319(8) 0.57114(18) -0.00799(7) 0.0198(2) Uani d . 1 . .
C C3 0.20711(11) 0.6783(2) -0.02684(10) 0.0169(3) Uani d . 1 . .
C C4 0.16230(12) 0.8635(3) -0.05922(10) 0.0197(3) Uani d . 1 . .
H H4 0.1064 0.9001 -0.0594 0.024 Uiso calc R 1 . .
C C5 0.19875(13) 0.9949(3) -0.09131(11) 0.0244(4) Uani d . 1 . .
H H5 0.1687 1.1222 -0.1121 0.029 Uiso calc R 1 . .
C C6 0.27903(13) 0.9406(3) -0.09309(11) 0.0270(4) Uani d . 1 . .
H H6 0.3033 1.0292 -0.1159 0.032 Uiso calc R 1 . .
C C7 0.32341(14) 0.7558(3) -0.06128(12) 0.0294(4) Uani d . 1 . .
H H7 0.3782 0.7180 -0.0626 0.035 Uiso calc R 1 . .
C C8 0.28878(13) 0.6261(3) -0.02765(11) 0.0233(4) Uani d . 1 . .
H H8 0.3206 0.5011 -0.0050 0.028 Uiso calc R 1 . .
C C9 0.37728(11) 0.1401(2) 0.17925(10) 0.0160(3) Uani d . 1 . .
C C10 0.45195(12) 0.1401(2) 0.26411(10) 0.0162(3) Uani d . 1 . .
C C11 0.55020(11) 0.1405(2) 0.29205(10) 0.0170(3) Uani d . 1 . .
H H11 0.6005 0.1393 0.3499 0.020 Uiso calc R 1 . .
C C12 0.57271(11) 0.1428(2) 0.23292(11) 0.0173(3) Uani d . 1 . .
C C13 0.50041(12) 0.1377(2) 0.14848(10) 0.0186(3) Uani d . 1 . .
H H13 0.5175 0.1366 0.1091 0.022 Uiso calc R 1 . .
C C14 0.40293(12) 0.1341(2) 0.12201(10) 0.0184(3) Uani d . 1 . .
H H14 0.3530 0.1276 0.0642 0.022 Uiso calc R 1 . .
Cl Cl1 0.42229(3) 0.14079(6) 0.33735(2) 0.02082(11) Uani d . 1 . .
Cl Cl2 0.69542(3) 0.15526(6) 0.26631(3) 0.02167(11) Uani d . 1 . .
C C15 0.10396(11) 0.1209(2) 0.13708(10) 0.0160(3) Uani d . 1 . .
C C16 0.11539(12) 0.1817(3) 0.21063(11) 0.0216(3) Uani d . 1 . .
H H16 0.1332 0.3162 0.2295 0.026 Uiso calc R 1 . .
C C17 0.10044(13) 0.0438(3) 0.25644(11) 0.0259(4) Uani d . 1 . .
H H17 0.1086 0.0843 0.3069 0.031 Uiso calc R 1 . .
C C18 0.07378(12) -0.1519(3) 0.22886(11) 0.0237(4) Uani d . 1 . .
H H18 0.0639 -0.2454 0.2605 0.028 Uiso calc R 1 . .
C C19 0.06150(12) -0.2117(3) 0.15488(11) 0.0224(4) Uani d . 1 . .
H H19 0.0423 -0.3454 0.1355 0.027 Uiso calc R 1 . .
C C20 0.07740(11) -0.0753(3) 0.10929(10) 0.0191(3) Uani d . 1 . .
H H20 0.0701 -0.1165 0.0592 0.023 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'
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
O1 C1 N1 . . 127.45(15) ?
O1 C1 C3 . . 119.26(14) ?
N1 C1 C3 . . 113.27(13) ?
C2 N1 C1 . . 119.92(13) ?
C2 N2 C9 . . 125.14(14) ?
C2 N2 H2 . . 117.2(13) ?
C9 N2 H2 . . 115.8(13) ?
C2 N3 C15 . . 122.90(14) ?
C2 N3 H3 . . 115.4(14) ?
C15 N3 H3 . . 121.7(14) ?
N1 C2 N3 . . 126.61(14) ?
N1 C2 N2 . . 117.82(14) ?
N3 C2 N2 . . 115.56(14) ?
C4 C3 C8 . . 119.04(15) ?
C4 C3 C1 . . 119.33(14) ?
C8 C3 C1 . . 121.63(15) ?
C5 C4 C3 . . 120.48(16) ?
C5 C4 H4 . . 119.8 ?
C3 C4 H4 . . 119.8 ?
C6 C5 C4 . . 120.14(17) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C7 C6 C5 . . 119.44(17) ?
C7 C6 H6 . . 120.3 ?
C5 C6 H6 . . 120.3 ?
C8 C7 C6 . . 120.71(17) ?
C8 C7 H7 . . 119.6 ?
C6 C7 H7 . . 119.6 ?
C7 C8 C3 . . 120.18(17) ?
C7 C8 H8 . . 119.9 ?
C3 C8 H8 . . 119.9 ?
C14 C9 C10 . . 118.64(15) ?
C14 C9 N2 . . 121.60(14) ?
C10 C9 N2 . . 119.71(15) ?
C11 C10 C9 . . 121.57(15) ?
C11 C10 Cl1 . . 118.64(13) ?
C9 C10 Cl1 . . 119.79(13) ?
C10 C11 C12 . . 117.98(15) ?
C10 C11 H11 . . 121.0 ?
C12 C11 H11 . . 121.0 ?
C13 C12 C11 . . 121.75(15) ?
C13 C12 Cl2 . . 119.34(13) ?
C11 C12 Cl2 . . 118.91(12) ?
C12 C13 C14 . . 119.28(16) ?
C12 C13 H13 . . 120.4 ?
C14 C13 H13 . . 120.4 ?
C13 C14 C9 . . 120.69(15) ?
C13 C14 H14 . . 119.7 ?
C9 C14 H14 . . 119.7 ?
C20 C15 C16 . . 120.33(15) ?
C20 C15 N3 . . 119.68(15) ?
C16 C15 N3 . . 119.97(15) ?
C15 C16 C17 . . 119.43(16) ?
C15 C16 H16 . . 120.3 ?
C17 C16 H16 . . 120.3 ?
C18 C17 C16 . . 120.42(17) ?
C18 C17 H17 . . 119.8 ?
C16 C17 H17 . . 119.8 ?
C17 C18 C19 . . 119.99(16) ?
C17 C18 H18 . . 120.0 ?
C19 C18 H18 . . 120.0 ?
C18 C19 C20 . . 119.90(16) ?
C18 C19 H19 . . 120.1 ?
C20 C19 H19 . . 120.1 ?
C15 C20 C19 . . 119.93(16) ?
C15 C20 H20 . . 120.0 ?
C19 C20 H20 . . 120.0 ?
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
C1 O1 . 1.2447(19) ?
C1 N1 . 1.359(2) ?
C1 C3 . 1.504(2) ?
N1 C2 . 1.329(2) ?
N2 C2 . 1.367(2) ?
N2 C9 . 1.411(2) ?
N2 H2 . 0.86(2) ?
N3 C2 . 1.339(2) ?
N3 C15 . 1.433(2) ?
N3 H3 . 0.84(2) ?
C3 C4 . 1.393(2) ?
C3 C8 . 1.397(2) ?
C4 C5 . 1.390(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.389(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.388(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.383(3) ?
C7 H7 . 0.9500 ?
C8 H8 . 0.9500 ?
C9 C14 . 1.392(2) ?
C9 C10 . 1.397(2) ?
C10 C11 . 1.388(2) ?
C10 Cl1 . 1.7412(17) ?
C11 C12 . 1.388(2) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.384(2) ?
C12 Cl2 . 1.7439(17) ?
C13 C14 . 1.384(2) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
C15 C20 . 1.388(2) ?
C15 C16 . 1.390(2) ?
C16 C17 . 1.392(3) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.384(3) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.390(3) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.391(2) ?
C19 H19 . 0.9500 ?
C20 H20 . 0.9500 ?
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
N3 H3 O1 . 0.84(2) 2.01(2) 2.6471(19) 132.7(18)
N3 H3 O1 3_565 0.84(2) 2.36(2) 3.032(2) 138.2(18)
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
O1 C1 N1 C2 . . . . -3.8(3) ?
C3 C1 N1 C2 . . . . 174.94(14) ?
C1 N1 C2 N3 . . . . 6.2(2) ?
C1 N1 C2 N2 . . . . -172.70(14) ?
C15 N3 C2 N1 . . . . -179.82(15) ?
C15 N3 C2 N2 . . . . -0.9(2) ?
C9 N2 C2 N1 . . . . 8.0(2) ?
C9 N2 C2 N3 . . . . -171.02(15) ?
O1 C1 C3 C4 . . . . 15.7(2) ?
N1 C1 C3 C4 . . . . -163.16(14) ?
O1 C1 C3 C8 . . . . -164.54(16) ?
N1 C1 C3 C8 . . . . 16.6(2) ?
C8 C3 C4 C5 . . . . -0.5(2) ?
C1 C3 C4 C5 . . . . 179.28(15) ?
C3 C4 C5 C6 . . . . 1.5(3) ?
C4 C5 C6 C7 . . . . -1.1(3) ?
C5 C6 C7 C8 . . . . -0.3(3) ?
C6 C7 C8 C3 . . . . 1.3(3) ?
C4 C3 C8 C7 . . . . -0.9(3) ?
C1 C3 C8 C7 . . . . 179.35(16) ?
C2 N2 C9 C14 . . . . -53.8(2) ?
C2 N2 C9 C10 . . . . 128.62(17) ?
C14 C9 C10 C11 . . . . 2.0(2) ?
N2 C9 C10 C11 . . . . 179.58(14) ?
C14 C9 C10 Cl1 . . . . -178.31(12) ?
N2 C9 C10 Cl1 . . . . -0.7(2) ?
C9 C10 C11 C12 . . . . 0.6(2) ?
Cl1 C10 C11 C12 . . . . -179.13(12) ?
C10 C11 C12 C13 . . . . -2.3(2) ?
C10 C11 C12 Cl2 . . . . 177.02(12) ?
C11 C12 C13 C14 . . . . 1.3(2) ?
Cl2 C12 C13 C14 . . . . -177.99(12) ?
C12 C13 C14 C9 . . . . 1.4(2) ?
C10 C9 C14 C13 . . . . -3.0(2) ?
N2 C9 C14 C13 . . . . 179.45(15) ?
C2 N3 C15 C20 . . . . -82.0(2) ?
C2 N3 C15 C16 . . . . 96.34(19) ?
C20 C15 C16 C17 . . . . 0.3(2) ?
N3 C15 C16 C17 . . . . -178.04(15) ?
C15 C16 C17 C18 . . . . -0.4(3) ?
C16 C17 C18 C19 . . . . -0.2(3) ?
C17 C18 C19 C20 . . . . 0.9(3) ?
C16 C15 C20 C19 . . . . 0.4(2) ?
N3 C15 C20 C19 . . . . 178.77(14) ?
C18 C19 C20 C15 . . . . -1.0(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743179
