#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/01/4510117.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_4510117
loop_
_publ_author_name
'Pan, Fangfang'
'Englert, Ulli'
_publ_section_title
;
 N-(6-Methyl-2-pyridyl)mesitylenesulfonamide: An Efficient Template for
 Polyiodides
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1057
_journal_paper_doi               10.1021/cg4015477
_journal_volume                  14
_journal_year                    2014
_chemical_formula_sum            'C18 H22 I2 N2 O2 S'
_chemical_formula_weight         584.24
_chemical_name_systematic
; 
 ? 
;
_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                94.0410(10)
_cell_angle_beta                 104.4000(10)
_cell_angle_gamma                90.7170(10)
_cell_formula_units_Z            2
_cell_length_a                   8.8726(8)
_cell_length_b                   10.5812(9)
_cell_length_c                   11.2061(10)
_cell_measurement_reflns_used    4632
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.9289
_cell_measurement_theta_min      2.3711
_cell_volume                     1015.98(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'SMART CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_source         'Incoatec microsource'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15108
_diffrn_reflns_theta_full        29.50
_diffrn_reflns_theta_max         29.50
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    3.212
_exptl_absorpt_correction_T_max  0.8559
_exptl_absorpt_correction_T_min  0.5659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.910
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.701
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         5602
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0254
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0246P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0542
_refine_ls_wR_factor_ref         0.0573
_reflns_number_gt                4877
_reflns_number_total             5602
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg4015477_si_001.cif
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4510117
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
I1 I 0.801187(18) -0.194517(14) 0.247129(14) 0.01756(5) Uani 1 1 d .
I2 I 0.926682(18) -0.416886(15) 0.065843(15) 0.02014(5) Uani 1 1 d .
S1 S 0.70894(7) 0.22960(6) 0.12829(5) 0.01467(12) Uani 1 1 d .
O1 O 0.85726(19) 0.19324(16) 0.11180(16) 0.0196(4) Uani 1 1 d .
O2 O 0.6018(2) 0.28499(16) 0.03073(15) 0.0183(4) Uani 1 1 d .
N1 N 0.4430(2) -0.04569(19) 0.18457(18) 0.0145(4) Uani 1 1 d .
H1N H 0.523(3) -0.095(2) 0.208(2) 0.020(7) Uiso 1 1 d .
N2 N 0.6272(2) 0.09206(19) 0.1484(2) 0.0157(4) Uani 1 1 d .
H2N H 0.682(3) 0.034(3) 0.165(3) 0.026(8) Uiso 1 1 d .
C1 C 0.4734(3) 0.0695(2) 0.1483(2) 0.0138(5) Uani 1 1 d .
C2 C 0.3002(3) -0.0866(2) 0.1907(2) 0.0161(5) Uani 1 1 d .
C3 C 0.1777(3) -0.0071(2) 0.1578(2) 0.0200(5) Uani 1 1 d .
H3 H 0.0760 -0.0329 0.1613 0.024 Uiso 1 1 calc R
C4 C 0.2044(3) 0.1111(2) 0.1195(2) 0.0204(5) Uani 1 1 d .
H4 H 0.1199 0.1661 0.0967 0.025 Uiso 1 1 calc R
C5 C 0.3518(3) 0.1505(2) 0.1139(2) 0.0189(5) Uani 1 1 d .
H5 H 0.3689 0.2313 0.0869 0.023 Uiso 1 1 calc R
C6 C 0.2872(3) -0.2177(2) 0.2291(2) 0.0196(5) Uani 1 1 d .
H6A H 0.2713 -0.2785 0.1566 0.029 Uiso 1 1 calc R
H6B H 0.1987 -0.2241 0.2663 0.029 Uiso 1 1 calc R
H6C H 0.3831 -0.2367 0.2896 0.029 Uiso 1 1 calc R
C7 C 0.7321(3) 0.3232(2) 0.2698(2) 0.0145(5) Uani 1 1 d .
C8 C 0.6401(3) 0.4308(2) 0.2779(2) 0.0161(5) Uani 1 1 d .
C9 C 0.6616(3) 0.4950(2) 0.3938(2) 0.0177(5) Uani 1 1 d .
H9 H 0.6007 0.5669 0.4014 0.021 Uiso 1 1 calc R
C10 C 0.7674(3) 0.4597(2) 0.4990(2) 0.0178(5) Uani 1 1 d .
C11 C 0.8586(3) 0.3561(2) 0.4864(2) 0.0183(5) Uani 1 1 d .
H11 H 0.9337 0.3325 0.5571 0.022 Uiso 1 1 calc R
C12 C 0.8440(3) 0.2856(2) 0.3741(2) 0.0161(5) Uani 1 1 d .
C13 C 0.5296(3) 0.4875(2) 0.1723(2) 0.0203(5) Uani 1 1 d .
H13A H 0.4908 0.5667 0.2024 0.031 Uiso 1 1 calc R
H13B H 0.4420 0.4278 0.1368 0.031 Uiso 1 1 calc R
H13C H 0.5842 0.5049 0.1089 0.031 Uiso 1 1 calc R
C14 C 0.7844(3) 0.5322(2) 0.6223(2) 0.0242(6) Uani 1 1 d .
H14A H 0.7203 0.6073 0.6116 0.036 Uiso 1 1 calc R
H14B H 0.8937 0.5585 0.6570 0.036 Uiso 1 1 calc R
H14C H 0.7502 0.4780 0.6786 0.036 Uiso 1 1 calc R
C15 C 0.9522(3) 0.1768(2) 0.3727(2) 0.0208(5) Uani 1 1 d .
H15A H 0.8910 0.0989 0.3387 0.031 Uiso 1 1 calc R
H15B H 1.0125 0.1659 0.4571 0.031 Uiso 1 1 calc R
H15C H 1.0232 0.1950 0.3212 0.031 Uiso 1 1 calc R
C16 C 0.5408(3) 0.1174(3) 0.4685(2) 0.0267(6) Uani 1 1 d .
H16 H 0.5684 0.1982 0.4470 0.032 Uiso 1 1 calc R
C17 C 0.3480(3) -0.0271(3) 0.5043(3) 0.0270(6) Uani 1 1 d .
H17 H 0.2439 -0.0454 0.5073 0.032 Uiso 1 1 calc R
C18 C 0.3885(3) 0.0912(3) 0.4724(2) 0.0263(6) Uani 1 1 d .
H18 H 0.3121 0.1538 0.4534 0.032 Uiso 1 1 calc R
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'
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
O2 S1 O1 119.35(11) .
O2 S1 N2 106.74(11) .
O1 S1 N2 102.97(10) .
O2 S1 C7 110.77(11) .
O1 S1 C7 110.14(11) .
N2 S1 C7 105.65(11) .
C2 N1 C1 124.0(2) .
C2 N1 H1N 118.9(17) .
C1 N1 H1N 117.0(17) .
C1 N2 S1 126.97(17) .
C1 N2 H2N 115(2) .
S1 N2 H2N 118(2) .
N1 C1 N2 114.6(2) .
N1 C1 C5 118.6(2) .
N2 C1 C5 126.7(2) .
N1 C2 C3 118.3(2) .
N1 C2 C6 116.8(2) .
C3 C2 C6 124.9(2) .
C2 C3 C4 119.2(2) .
C2 C3 H3 120.4 .
C4 C3 H3 120.4 .
C5 C4 C3 121.3(2) .
C5 C4 H4 119.3 .
C3 C4 H4 119.3 .
C1 C5 C4 118.5(2) .
C1 C5 H5 120.7 .
C4 C5 H5 120.7 .
C2 C6 H6A 109.5 .
C2 C6 H6B 109.5 .
H6A C6 H6B 109.5 .
C2 C6 H6C 109.5 .
H6A C6 H6C 109.5 .
H6B C6 H6C 109.5 .
C12 C7 C8 121.5(2) .
C12 C7 S1 117.57(18) .
C8 C7 S1 120.92(18) .
C9 C8 C7 116.8(2) .
C9 C8 C13 116.6(2) .
C7 C8 C13 126.5(2) .
C10 C9 C8 123.6(2) .
C10 C9 H9 118.2 .
C8 C9 H9 118.2 .
C9 C10 C11 117.8(2) .
C9 C10 C14 121.2(2) .
C11 C10 C14 121.0(2) .
C10 C11 C12 122.5(2) .
C10 C11 H11 118.8 .
C12 C11 H11 118.8 .
C11 C12 C7 117.8(2) .
C11 C12 C15 117.1(2) .
C7 C12 C15 125.1(2) .
C8 C13 H13A 109.5 .
C8 C13 H13B 109.5 .
H13A C13 H13B 109.5 .
C8 C13 H13C 109.5 .
H13A C13 H13C 109.5 .
H13B C13 H13C 109.5 .
C10 C14 H14A 109.5 .
C10 C14 H14B 109.5 .
H14A C14 H14B 109.5 .
C10 C14 H14C 109.5 .
H14A C14 H14C 109.5 .
H14B C14 H14C 109.5 .
C12 C15 H15A 109.5 .
C12 C15 H15B 109.5 .
H15A C15 H15B 109.5 .
C12 C15 H15C 109.5 .
H15A C15 H15C 109.5 .
H15B C15 H15C 109.5 .
C17 C16 C18 120.4(3) 2_656
C17 C16 H16 119.8 2_656
C18 C16 H16 119.8 .
C16 C17 C18 119.8(3) 2_656
C16 C17 H17 120.1 2_656
C18 C17 H17 120.1 .
C16 C18 C17 119.8(3) .
C16 C18 H18 120.1 .
C17 C18 H18 120.1 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I2 I2 2.7587(4) 2_745
S1 O2 1.4247(17) .
S1 O1 1.4274(17) .
S1 N2 1.672(2) .
S1 C7 1.775(2) .
N1 C2 1.353(3) .
N1 C1 1.357(3) .
N1 H1N 0.88(3) .
N2 C1 1.382(3) .
N2 H2N 0.79(3) .
C1 C5 1.382(3) .
C2 C3 1.376(3) .
C2 C6 1.493(3) .
C3 C4 1.387(3) .
C3 H3 0.9500 .
C4 C5 1.385(3) .
C4 H4 0.9500 .
C5 H5 0.9500 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 C12 1.417(3) .
C7 C8 1.420(3) .
C8 C9 1.390(3) .
C8 C13 1.503(3) .
C9 C10 1.389(3) .
C9 H9 0.9500 .
C10 C11 1.391(3) .
C10 C14 1.505(3) .
C11 C12 1.393(3) .
C11 H11 0.9500 .
C12 C15 1.510(3) .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 C17 1.377(4) 2_656
C16 C18 1.388(4) .
C16 H16 0.9500 .
C17 C16 1.377(4) 2_656
C17 C18 1.393(4) .
C17 H17 0.9500 .
C18 H18 0.9500 .
