#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/95/1519562.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1519562
loop_
_publ_author_name
'Bricklebank, Neil'
'Coles, Simon J.'
'Hursthouse, Michael B.'
_publ_section_title
;
 C19H21I4N4S3
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              901
_journal_year                    2003
_chemical_formula_sum            'C19 H21 I4 N4 S3'
_chemical_formula_weight         909.18
_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
_cell_angle_alpha                100.0980(10)
_cell_angle_beta                 95.7330(10)
_cell_angle_gamma                110.7060(10)
_cell_formula_units_Z            2
_cell_length_a                   9.14320(10)
_cell_length_b                   9.9264(2)
_cell_length_c                   16.5802(3)
_cell_measurement_reflns_used    16740
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1364.22(4)
_computing_cell_refinement       'DENZO and COLLECT'
_computing_data_collection
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_data_reduction        'DENZO and COLLECT'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method       'ω and φ scans to fill Ewald sphere'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11625
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    4.812
_exptl_absorpt_correction_T_max  0.8308
_exptl_absorpt_correction_T_min  0.5523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing, 1997)'
_exptl_crystal_colour            dark
_exptl_crystal_density_diffrn    2.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             846
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.283
_refine_diff_density_min         -1.559
_refine_diff_density_rms         0.158
_refine_ls_extinction_coef       0.0023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         6195
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0478P)²+3.5475P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0970
_reflns_number_gt                5457
_reflns_number_total             6195
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-901.cif
_cod_data_source_block           03src0294
_cod_depositor_comments
;
Citation :
Bricklebank, Neil and Coles, Simon J. and Hursthouse, Michael B. (2003) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/901)

More at:
http://ecrystals.chem.soton.ac.uk/901/

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1519562
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C13 C 0.1820(6) 0.5236(5) 0.4610(3) 0.0316(10) Uani 1 1 d . . .
H13 H 0.2253 0.5073 0.5112 0.038 Uiso 1 1 calc R . .
C14 C 0.2046(6) 0.6598(5) 0.4470(3) 0.0316(10) Uani 1 1 d . . .
H14 H 0.2653 0.7495 0.4864 0.038 Uiso 1 1 calc R . .
C15 C 0.1279(5) 0.6532(5) 0.3675(3) 0.0263(9) Uani 1 1 d . . .
H15 H 0.1309 0.7379 0.3475 0.032 Uiso 1 1 calc R . .
C16 C 0.0487(5) 0.5113(4) 0.3226(2) 0.0200(8) Uani 1 1 d . . .
C17 C -0.0467(4) 0.4657(4) 0.2399(2) 0.0179(7) Uani 1 1 d . . .
C18 C -0.2263(5) 0.3219(4) 0.1224(2) 0.0236(8) Uani 1 1 d . . .
H18A H -0.3401 0.2918 0.1269 0.028 Uiso 1 1 calc R . .
H18B H -0.2142 0.2530 0.0751 0.028 Uiso 1 1 calc R . .
C19 C -0.1557(5) 0.4828(5) 0.1132(3) 0.0283(9) Uani 1 1 d . . .
H19A H -0.0880 0.4925 0.0699 0.034 Uiso 1 1 calc R . .
H19B H -0.2403 0.5197 0.0992 0.034 Uiso 1 1 calc R . .
N3 N -0.1297(4) 0.3283(3) 0.2005(2) 0.0198(7) Uani 1 1 d D . .
N4 N -0.0614(4) 0.5619(4) 0.1959(2) 0.0210(7) Uani 1 1 d D . .
H3N H -0.132(8) 0.248(5) 0.224(4) 0.053(18) Uiso 1 1 d D . .
H4N H 0.005(4) 0.6632(16) 0.208(3) 0.013(10) Uiso 1 1 d D . .
C1 C 0.4384(6) 0.6994(5) 0.0719(3) 0.0323(10) Uani 1 1 d . . .
H1 H 0.4679 0.6178 0.0541 0.039 Uiso 1 1 calc R . .
C2 C 0.5135(5) 0.8347(5) 0.0591(3) 0.0289(9) Uani 1 1 d . . .
H2 H 0.6017 0.8589 0.0310 0.035 Uiso 1 1 calc R . .
C3 C 0.4476(5) 0.9393(4) 0.0921(2) 0.0217(8) Uani 1 1 d . . .
H3 H 0.4865 1.0403 0.0892 0.026 Uiso 1 1 calc R . .
C4 C 0.3185(4) 0.8722(4) 0.1290(2) 0.0184(7) Uani 1 1 d . . .
C5 C 0.2297(5) 0.9484(4) 0.1732(2) 0.0185(7) Uani 1 1 d . . .
H5 H 0.2607 1.0515 0.1765 0.022 Uiso 1 1 calc R . .
C6 C 0.0395(5) 0.9834(4) 0.2480(2) 0.0218(8) Uani 1 1 d . . .
H6A H 0.1097 1.0881 0.2544 0.026 Uiso 1 1 calc R . .
H6B H 0.0241 0.9658 0.3041 0.026 Uiso 1 1 calc R . .
C7 C -0.1197(5) 0.9519(4) 0.1954(2) 0.0207(8) Uani 1 1 d . . .
H7A H -0.1029 0.9794 0.1415 0.025 Uiso 1 1 calc R . .
H7B H -0.1853 0.8449 0.1840 0.025 Uiso 1 1 calc R . .
C8 C -0.3125(5) 0.9640(4) 0.2748(2) 0.0185(7) Uani 1 1 d . . .
H8 H -0.3318 0.8622 0.2707 0.022 Uiso 1 1 calc R . .
C9 C -0.4087(5) 1.0254(4) 0.3211(2) 0.0178(7) Uani 1 1 d . . .
C10 C -0.5161(5) 0.9531(4) 0.3671(3) 0.0241(8) Uani 1 1 d . . .
H10 H -0.5351 0.8551 0.3729 0.029 Uiso 1 1 calc R . .
C11 C -0.5949(5) 1.0408(5) 0.4046(3) 0.0268(9) Uani 1 1 d . . .
H11 H -0.6720 1.0086 0.4387 0.032 Uiso 1 1 calc R . .
C12 C -0.5475(5) 1.1767(5) 0.3861(3) 0.0245(8) Uani 1 1 d . . .
H12 H -0.5888 1.2495 0.4054 0.029 Uiso 1 1 calc R . .
N1 N 0.1139(4) 0.8861(3) 0.2076(2) 0.0189(6) Uani 1 1 d . . .
N2 N -0.2034(4) 1.0365(4) 0.2389(2) 0.0182(6) Uani 1 1 d . . .
S1 S 0.28334(15) 0.68996(12) 0.12379(8) 0.0353(3) Uani 1 1 d . . .
S2 S -0.40522(12) 1.20139(10) 0.32425(6) 0.0208(2) Uani 1 1 d . . .
S3 S 0.06683(14) 0.38478(12) 0.37803(7) 0.0295(2) Uani 1 1 d . . .
I1 I 0.35740(3) 0.39171(3) 0.191454(18) 0.02834(10) Uani 1 1 d . . .
I2 I 0.12818(4) 0.23004(4) 0.042970(19) 0.03543(11) Uani 1 1 d . . .
I3 I 0.58271(5) 0.56909(4) 0.34761(3) 0.05666(14) Uani 1 1 d . . .
I4 I 0.88114(4) 0.86880(3) 0.456525(18) 0.03158(10) Uani 1 1 d . . .
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C14 C13 S3 112.4(3) . .
C14 C13 H13 123.8 . .
S3 C13 H13 123.8 . .
C13 C14 C15 112.5(4) . .
C13 C14 H14 123.8 . .
C15 C14 H14 123.8 . .
C16 C15 C14 112.5(4) . .
C16 C15 H15 123.8 . .
C14 C15 H15 123.8 . .
C15 C16 C17 126.5(4) . .
C15 C16 S3 111.6(3) . .
C17 C16 S3 121.9(3) . .
N3 C17 N4 112.2(3) . .
N3 C17 C16 125.0(3) . .
N4 C17 C16 122.7(3) . .
N3 C18 C19 102.0(3) . .
N3 C18 H18A 111.4 . .
C19 C18 H18A 111.4 . .
N3 C18 H18B 111.4 . .
C19 C18 H18B 111.4 . .
H18A C18 H18B 109.2 . .
N4 C19 C18 102.8(3) . .
N4 C19 H19A 111.2 . .
C18 C19 H19A 111.2 . .
N4 C19 H19B 111.2 . .
C18 C19 H19B 111.2 . .
H19A C19 H19B 109.1 . .
C17 N3 C18 110.8(3) . .
C17 N3 H3N 122(4) . .
C18 N3 H3N 127(4) . .
C17 N4 C19 110.0(3) . .
C17 N4 H4N 124(3) . .
C19 N4 H4N 123(3) . .
C2 C1 S1 112.5(3) . .
C2 C1 H1 123.7 . .
S1 C1 H1 123.7 . .
C1 C2 C3 113.3(4) . .
C1 C2 H2 123.3 . .
C3 C2 H2 123.3 . .
C4 C3 C2 110.6(4) . .
C4 C3 H3 124.7 . .
C2 C3 H3 124.7 . .
C3 C4 C5 125.1(3) . .
C3 C4 S1 112.0(3) . .
C5 C4 S1 122.7(3) . .
N1 C5 C4 124.3(3) . .
N1 C5 H5 117.9 . .
C4 C5 H5 117.9 . .
N1 C6 C7 109.5(3) . .
N1 C6 H6A 109.8 . .
C7 C6 H6A 109.8 . .
N1 C6 H6B 109.8 . .
C7 C6 H6B 109.8 . .
H6A C6 H6B 108.2 . .
N2 C7 C6 110.3(3) . .
N2 C7 H7A 109.6 . .
C6 C7 H7A 109.6 . .
N2 C7 H7B 109.6 . .
C6 C7 H7B 109.6 . .
H7A C7 H7B 108.1 . .
N2 C8 C9 124.7(4) . .
N2 C8 H8 117.7 . .
C9 C8 H8 117.7 . .
C10 C9 C8 125.5(4) . .
C10 C9 S2 111.0(3) . .
C8 C9 S2 123.4(3) . .
C9 C10 C11 112.7(4) . .
C9 C10 H10 123.7 . .
C11 C10 H10 123.7 . .
C12 C11 C10 112.3(4) . .
C12 C11 H11 123.9 . .
C10 C11 H11 123.9 . .
C11 C12 S2 112.4(3) . .
C11 C12 H12 123.8 . .
S2 C12 H12 123.8 . .
C5 N1 C6 115.5(3) . .
C8 N2 C7 115.5(3) . .
C4 S1 C1 91.6(2) . .
C12 S2 C9 91.6(2) . .
C13 S3 C16 91.1(2) . .
I2 I1 I3 176.618(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C13 C14 1.359(7) .
C13 S3 1.708(4) .
C13 H13 0.9500 .
C14 C15 1.409(6) .
C14 H14 0.9500 .
C15 C16 1.366(6) .
C15 H15 0.9500 .
C16 C17 1.452(5) .
C16 S3 1.724(4) .
C17 N3 1.312(5) .
C17 N4 1.334(5) .
C18 N3 1.471(5) .
C18 C19 1.538(6) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 N4 1.465(5) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
N3 H3N 0.946(10) .
N4 H4N 0.944(10) .
C1 C2 1.340(7) .
C1 S1 1.714(5) .
C1 H1 0.9500 .
C2 C3 1.431(6) .
C2 H2 0.9500 .
C3 C4 1.394(5) .
C3 H3 0.9500 .
C4 C5 1.458(6) .
C4 S1 1.707(4) .
C5 N1 1.269(5) .
C5 H5 0.9500 .
C6 N1 1.474(5) .
C6 C7 1.520(5) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 N2 1.471(5) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 N2 1.275(5) .
C8 C9 1.444(5) .
C8 H8 0.9500 .
C9 C10 1.379(6) .
C9 S2 1.728(4) .
C10 C11 1.418(6) .
C10 H10 0.9500 .
C11 C12 1.364(6) .
C11 H11 0.9500 .
C12 S2 1.713(4) .
C12 H12 0.9500 .
I1 I2 2.8695(4) .
I1 I3 2.9696(5) .
I4 I4 2.7642(6) 2_776
