#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/03/2230308.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_2230308
loop_
_publ_author_name
'Mat Rashid, Fatisha Liyana'
'Heng, Lee Yook'
'Daran, Jean-Claude'
'Kassim, Mohammad B.'
_publ_section_title
;
 N-Benzoyl-N'-(1,10-phenanthrolin-5-yl)thiourea
 dichloromethane hemisolvate monohydrate
;
_journal_coeditor_code           FJ2403
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1397
_journal_page_last               o1398
_journal_paper_doi               10.1107/S160053681101734X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C20 H14 N4 O S, 0.5C H2 Cl2, H2 O'
_chemical_formula_moiety         'C20 H14 N4 O S, 0.5(C H2 Cl2), H2 O'
_chemical_formula_sum            'C20.5 H17 Cl N4 O2 S'
_chemical_formula_weight         418.89
_chemical_name_systematic
;
N-Benzoyl-N'-(1,10-phenanthrolin-5-yl)thiourea
dichloromethane hemisolvate monohydrate
;
_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                112.949(5)
_cell_angle_beta                 103.984(5)
_cell_angle_gamma                96.641(5)
_cell_formula_units_Z            2
_cell_length_a                   9.385(5)
_cell_length_b                   10.863(5)
_cell_length_c                   10.927(5)
_cell_measurement_reflns_used    4905
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.38
_cell_measurement_theta_min      2.10
_cell_volume                     967.6(8)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia,
1997) and
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON
(Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type
;
Bruker SMART APEX CCD area-detector
;
_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  0.0144
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4400
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_T_max  0.9740
_exptl_absorpt_correction_T_min  0.9163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             434
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.187
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3254
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0494
_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)+(0.0792P)²+0.0787P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1390
_reflns_number_gt                2450
_reflns_number_total             3254
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2403.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C20.50 H17 Cl N4 O2 S'
_cod_database_code               2230308
_cod_database_fobs_code          2230308
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C8 0.1675(2) 0.7038(2) 0.1383(2) 0.0355(5) Uani d . 1 1 . .
C C7 0.1658(3) 0.4881(2) 0.1675(2) 0.0392(6) Uani d . 1 1 . .
C C14 0.0884(3) 0.8891(2) 0.3010(2) 0.0376(5) Uani d . 1 1 . .
C C13 -0.0219(3) 0.9315(2) 0.2377(2) 0.0419(6) Uani d . 1 1 . .
H H13 -0.0864 0.8715 0.1488 0.050 Uiso calc R 1 1 . .
C C12 -0.0432(3) 1.0675(2) 0.3038(2) 0.0384(5) Uani d . 1 1 . .
C C20 0.0499(3) 1.1569(2) 0.4405(2) 0.0359(5) Uani d . 1 1 . .
C C19 0.1718(3) 1.1125(2) 0.5081(2) 0.0366(5) Uani d . 1 1 . .
C C15 0.1916(3) 0.9784(2) 0.4377(2) 0.0386(5) Uani d . 1 1 . .
C C1 0.2387(3) 0.3698(2) 0.1377(2) 0.0374(5) Uani d . 1 1 . .
C C6 0.3666(3) 0.3676(3) 0.0951(3) 0.0444(6) Uani d . 1 1 . .
H H6 0.4046 0.4380 0.0751 0.053 Uiso calc R 1 1 . .
C C5 0.4371(3) 0.2607(3) 0.0825(3) 0.0528(7) Uani d . 1 1 . .
H H5 0.5231 0.2593 0.0544 0.063 Uiso calc R 1 1 . .
C C4 0.3802(3) 0.1559(3) 0.1116(3) 0.0521(7) Uani d . 1 1 . .
H H4 0.4284 0.0843 0.1034 0.063 Uiso calc R 1 1 . .
C C3 0.2526(3) 0.1569(3) 0.1525(3) 0.0556(7) Uani d . 1 1 . .
H H3 0.2136 0.0853 0.1704 0.067 Uiso calc R 1 1 . .
C C2 0.1833(3) 0.2638(2) 0.1669(3) 0.0472(6) Uani d . 1 1 . .
H H2 0.0983 0.2653 0.1965 0.057 Uiso calc R 1 1 . .
C C11 -0.1558(3) 1.1162(3) 0.2395(3) 0.0490(6) Uani d . 1 1 . .
H H11 -0.2178 1.0612 0.1482 0.059 Uiso calc R 1 1 . .
C C10 -0.1746(3) 1.2442(3) 0.3108(3) 0.0533(7) Uani d . 1 1 . .
H H10 -0.2479 1.2787 0.2689 0.064 Uiso calc R 1 1 . .
C C9 -0.0820(3) 1.3217(3) 0.4472(3) 0.0506(7) Uani d . 1 1 . .
H H9 -0.0988 1.4074 0.4964 0.061 Uiso calc R 1 1 . .
C C16 0.3117(3) 0.9399(3) 0.5063(3) 0.0470(6) Uani d . 1 1 . .
H H16 0.3276 0.8523 0.4638 0.056 Uiso calc R 1 1 . .
C C17 0.4052(3) 1.0305(3) 0.6353(3) 0.0562(7) Uani d . 1 1 . .
H H17 0.4865 1.0067 0.6814 0.067 Uiso calc R 1 1 . .
C C18 0.3767(3) 1.1599(3) 0.6968(3) 0.0550(7) Uani d . 1 1 . .
H H18 0.4411 1.2211 0.7852 0.066 Uiso calc R 1 1 . .
N N1 0.1038(2) 0.75069(19) 0.2384(2) 0.0462(5) Uani d . 1 1 . .
H H1A 0.0695 0.6940 0.2674 0.055 Uiso calc R 1 1 . .
N N2 0.1897(2) 0.57097(18) 0.1030(2) 0.0384(5) Uani d . 1 1 . .
H H2A 0.2221 0.5371 0.0325 0.046 Uiso calc R 1 1 . .
N N3 0.2644(2) 1.2012(2) 0.6378(2) 0.0475(5) Uani d . 1 1 . .
N N4 0.0287(2) 1.2829(2) 0.5128(2) 0.0462(5) Uani d . 1 1 . .
O O1 0.0911(2) 0.51100(18) 0.2479(2) 0.0574(5) Uani d . 1 1 . .
S S1 0.22322(8) 0.79160(7) 0.05756(7) 0.0509(2) Uani d . 1 1 . .
O O2W 0.2509(2) 0.46575(19) -0.1633(2) 0.0658(6) Uani d . 1 1 . .
H H1W 0.2519 0.3976 -0.2352 0.099 Uiso d R 1 1 . .
H H2W 0.1823 0.5024 -0.1909 0.099 Uiso d R 1 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'
S S 0.1246 0.1234 '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
N1 C8 N2 . . 116.0(2) ?
N1 C8 S1 . . 124.83(17) ?
N2 C8 S1 . . 119.18(17) ?
O1 C7 N2 . . 122.2(2) ?
O1 C7 C1 . . 121.1(2) ?
N2 C7 C1 . . 116.7(2) ?
C13 C14 N1 . . 121.2(2) ?
C13 C14 C15 . . 121.4(2) ?
N1 C14 C15 . . 117.4(2) ?
C14 C13 C12 . . 121.3(2) ?
C14 C13 H13 . . 119.3 ?
C12 C13 H13 . . 119.3 ?
C11 C12 C20 . . 117.5(2) ?
C11 C12 C13 . . 122.8(2) ?
C20 C12 C13 . . 119.7(2) ?
N4 C20 C12 . . 122.7(2) ?
N4 C20 C19 . . 118.2(2) ?
C12 C20 C19 . . 119.1(2) ?
N3 C19 C15 . . 121.9(2) ?
N3 C19 C20 . . 118.7(2) ?
C15 C19 C20 . . 119.4(2) ?
C16 C15 C19 . . 117.6(2) ?
C16 C15 C14 . . 123.4(2) ?
C19 C15 C14 . . 119.0(2) ?
C6 C1 C2 . . 119.3(2) ?
C6 C1 C7 . . 122.8(2) ?
C2 C1 C7 . . 117.6(2) ?
C5 C6 C1 . . 119.9(2) ?
C5 C6 H6 . . 120.1 ?
C1 C6 H6 . . 120.1 ?
C6 C5 C4 . . 120.0(2) ?
C6 C5 H5 . . 120.0 ?
C4 C5 H5 . . 120.0 ?
C3 C4 C5 . . 120.4(2) ?
C3 C4 H4 . . 119.8 ?
C5 C4 H4 . . 119.8 ?
C2 C3 C4 . . 119.8(3) ?
C2 C3 H3 . . 120.1 ?
C4 C3 H3 . . 120.1 ?
C3 C2 C1 . . 120.7(2) ?
C3 C2 H2 . . 119.7 ?
C1 C2 H2 . . 119.7 ?
C10 C11 C12 . . 119.8(2) ?
C10 C11 H11 . . 120.1 ?
C12 C11 H11 . . 120.1 ?
C11 C10 C9 . . 118.3(2) ?
C11 C10 H10 . . 120.8 ?
C9 C10 H10 . . 120.8 ?
N4 C9 C10 . . 124.8(2) ?
N4 C9 H9 . . 117.6 ?
C10 C9 H9 . . 117.6 ?
C17 C16 C15 . . 119.9(2) ?
C17 C16 H16 . . 120.0 ?
C15 C16 H16 . . 120.0 ?
C16 C17 C18 . . 118.5(3) ?
C16 C17 H17 . . 120.7 ?
C18 C17 H17 . . 120.7 ?
N3 C18 C17 . . 124.2(3) ?
N3 C18 H18 . . 117.9 ?
C17 C18 H18 . . 117.9 ?
C8 N1 C14 . . 124.39(19) ?
C8 N1 H1A . . 117.8 ?
C14 N1 H1A . . 117.8 ?
C7 N2 C8 . . 127.66(19) ?
C7 N2 H2A . . 116.2 ?
C8 N2 H2A . . 116.2 ?
C18 N3 C19 . . 117.9(2) ?
C9 N4 C20 . . 116.8(2) ?
H1W O2W H2W . . 106.6 ?
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
C8 N1 . 1.329(3) ?
C8 N2 . 1.395(3) ?
C8 S1 . 1.651(2) ?
C7 O1 . 1.222(3) ?
C7 N2 . 1.372(3) ?
C7 C1 . 1.486(3) ?
C14 C13 . 1.331(3) ?
C14 N1 . 1.431(3) ?
C14 C15 . 1.437(3) ?
C13 C12 . 1.432(3) ?
C13 H13 . 0.9300 ?
C12 C11 . 1.397(4) ?
C12 C20 . 1.407(3) ?
C20 N4 . 1.354(3) ?
C20 C19 . 1.444(3) ?
C19 N3 . 1.355(3) ?
C19 C15 . 1.416(3) ?
C15 C16 . 1.398(3) ?
C1 C6 . 1.388(3) ?
C1 C2 . 1.388(3) ?
C6 C5 . 1.379(4) ?
C6 H6 . 0.9300 ?
C5 C4 . 1.381(4) ?
C5 H5 . 0.9300 ?
C4 C3 . 1.375(4) ?
C4 H4 . 0.9300 ?
C3 C2 . 1.371(4) ?
C3 H3 . 0.9300 ?
C2 H2 . 0.9300 ?
C11 C10 . 1.360(4) ?
C11 H11 . 0.9300 ?
C10 C9 . 1.383(4) ?
C10 H10 . 0.9300 ?
C9 N4 . 1.322(3) ?
C9 H9 . 0.9300 ?
C16 C17 . 1.358(4) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.391(4) ?
C17 H17 . 0.9300 ?
C18 N3 . 1.317(3) ?
C18 H18 . 0.9300 ?
N1 H1A . 0.8600 ?
N2 H2A . 0.8600 ?
O2W H1W . 0.8472 ?
O2W H2W . 0.8513 ?
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
N1 H1A O1 . 0.86 1.96 2.636(3) 135
N2 H2A O2W . 0.86 2.07 2.910(3) 165
O2W H1W N3 1_544 0.85 2.08 2.889(3) 160
O2W H2W O1 2_565 0.85 2.46 3.187(3) 144
C9 H9 O1 2_576 0.93 2.56 3.140(4) 121
C2 H2 Cg2 1_545 0.93 2.99 3.806(4) 147
C13 H13 Cg3 2_565 0.93 2.88 3.796(3) 168
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656697
