# Electronic Supplementary Material (ESI) for Molecular Systems Design & Engineering.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_gppw3
_database_code_depnum_ccdc_archive 'CCDC 1420386'
_audit_update_record             
;
2015-08-24 deposited with the CCDC.
2016-03-18 downloaded from the CCDC.
;

_audit_creation_date             2013-06-13T11:50:04-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 3,3'-Diethyloxacarbocyanine iodide
;
_chemical_formula_moiety         'C21 H21 N2 O2, I1'
_chemical_formula_sum            'C21 H21 I1 N2 O2'
_chemical_formula_analytical     ?
_chemical_formula_weight         460.3

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.838(3)
_cell_length_b                   10.358(3)
_cell_length_c                   21.781(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.634(5)
_cell_angle_gamma                90
_cell_volume                     1971.3(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5125
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      33
_cell_measurement_temperature    120(2)
_exptl_crystal_description       Prism
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    1.641
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'Higashi, 1995'
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_T_max  0.808

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
        Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            15924
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       26

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total             4507
_reflns_number_gt                4157
_reflns_threshold_expression     >2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1174
_refine_ls_wR_factor_obs         0.1174
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_number_reflns         4507
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0434P)²+4.4787P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         2.003
_refine_diff_density_min         -1.755
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
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 0 '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 0.006 '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'

_computing_data_collection       
;
        CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_cell_refinement       
;
        CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction        
;
        CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_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
_atom_site_type_symbol
C1 0.4310(3) 0.1674(3) 0.15329(15) 0.0207(6) Uani d . 1 . . C
C2 0.4625(3) 0.2441(3) 0.10405(15) 0.0217(6) Uani d . 1 . . C
C3 0.4123(4) 0.3690(3) 0.09483(18) 0.0285(7) Uani d . 1 . . C
H3 0.4364 0.4191 0.0622 0.034 Uiso calc R 1 . . H
C4 0.3223(4) 0.4163(4) 0.13770(17) 0.0305(7) Uani d . 1 . . C
H4 0.2849 0.5002 0.1336 0.037 Uiso calc R 1 . . H
C5 0.2880(4) 0.3396(4) 0.18647(17) 0.0294(7) Uani d . 1 . . C
H5 0.2265 0.3737 0.2136 0.035 Uiso calc R 1 . . H
C6 0.3427(4) 0.2138(3) 0.19601(16) 0.0256(7) Uani d . 1 . . C
H6 0.3211 0.1638 0.2291 0.031 Uiso calc R 1 . . H
C7 0.5730(3) 0.0550(3) 0.09534(15) 0.0214(6) Uani d . 1 . . C
C8 0.6596(3) -0.0401(3) 0.07294(15) 0.0223(6) Uani d . 1 . . C
H8 0.671 -0.1179 0.0945 0.027 Uiso calc R 1 . . H
C9 0.7313(3) -0.0282(3) 0.02024(15) 0.0214(6) Uani d . 1 . . C
H9 0.7173 0.0467 -0.0035 0.026 Uiso calc R 1 . . H
C10 0.8229(4) -0.1259(3) 0.00279(15) 0.0217(6) Uani d . 1 . . C
H10 0.8363 -0.1988 0.028 0.026 Uiso calc R 1 . . H
C11 0.8963(3) -0.1238(3) -0.04939(15) 0.0190(6) Uani d . 1 . . C
C12 1.0363(3) -0.1783(3) -0.12249(14) 0.0199(6) Uani d . 1 . . C
C13 0.9779(3) -0.0551(3) -0.13461(15) 0.0214(6) Uani d . 1 . . C
C14 1.0061(4) 0.0179(3) -0.18444(16) 0.0258(7) Uani d . 1 . . C
H14 0.9669 0.1007 -0.1917 0.031 Uiso calc R 1 . . H
C15 1.0979(4) -0.0410(4) -0.22345(15) 0.0273(7) Uani d . 1 . . C
H15 1.1198 0.0037 -0.2581 0.033 Uiso calc R 1 . . H
C16 1.1577(4) -0.1651(4) -0.21192(16) 0.0266(7) Uani d . 1 . . C
H16 1.2184 -0.2005 -0.239 0.032 Uiso calc R 1 . . H
C17 1.1285(4) -0.2373(3) -0.16081(15) 0.0229(6) Uani d . 1 . . C
H17 1.1683 -0.3197 -0.1529 0.028 Uiso calc R 1 . . H
C18 0.5096(4) -0.0629(3) 0.18843(16) 0.0256(7) Uani d . 1 . . C
H18A 0.4857 -0.0346 0.2283 0.031 Uiso calc R 1 . . H
H18B 0.613 -0.0969 0.1949 0.031 Uiso calc R 1 . . H
C19 0.3993(4) -0.1698(3) 0.16344(18) 0.0300(7) Uani d . 1 . . C
H19A 0.4263 -0.2019 0.1252 0.045 Uiso calc R 1 . . H
H19B 0.2969 -0.1363 0.1562 0.045 Uiso calc R 1 . . H
H19C 0.4051 -0.2387 0.1932 0.045 Uiso calc R 1 . . H
C20 1.0215(4) -0.3414(3) -0.03608(15) 0.0227(6) Uani d . 1 . . C
H20A 1.0322 -0.4081 -0.0664 0.027 Uiso calc R 1 . . H
H20B 0.939 -0.3662 -0.0138 0.027 Uiso calc R 1 . . H
C21 1.1691(4) -0.3309(4) 0.00919(18) 0.0318(8) Uani d . 1 . . C
H21A 1.1564 -0.2693 0.0409 0.048 Uiso calc R 1 . . H
H21B 1.2502 -0.3032 -0.0126 0.048 Uiso calc R 1 . . H
H21C 1.1943 -0.4136 0.0279 0.048 Uiso calc R 1 . . H
N1 0.5025(3) 0.0490(3) 0.14619(12) 0.0213(5) Uani d . 1 . . N
N2 0.9832(3) -0.2185(3) -0.06828(12) 0.0199(5) Uani d . 1 . . N
O1 0.5504(2) 0.1732(2) 0.06804(11) 0.0220(4) Uani d . 1 . . O
O2 0.8901(2) -0.0218(2) -0.08897(10) 0.0207(4) Uani d . 1 . . O
I1 1.12243(4) 0.37591(2) -0.143084(11) 0.04136(12) Uani d . 1 . . I



#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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 C6 . 1.387(5) ?
C1 C2 . 1.396(5) ?
C1 N1 . 1.399(4) ?
C2 C3 . 1.373(5) ?
C2 O1 . 1.393(4) ?
C3 C4 . 1.402(5) ?
C3 H3 . 0.93 ?
C4 C5 . 1.395(6) ?
C4 H4 . 0.93 ?
C5 C6 . 1.395(5) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C7 N1 . 1.352(4) ?
C7 O1 . 1.362(4) ?
C7 C8 . 1.381(4) ?
C8 C9 . 1.397(5) ?
C8 H8 . 0.93 ?
C9 C10 . 1.385(4) ?
C9 H9 . 0.93 ?
C10 C11 . 1.391(5) ?
C10 H10 . 0.93 ?
C11 N2 . 1.347(4) ?
C11 O2 . 1.359(4) ?
C12 C13 . 1.388(5) ?
C12 C17 . 1.392(5) ?
C12 N2 . 1.398(4) ?
C13 C14 . 1.376(5) ?
C13 O2 . 1.393(4) ?
C14 C15 . 1.400(5) ?
C14 H14 . 0.93 ?
C15 C16 . 1.398(5) ?
C15 H15 . 0.93 ?
C16 C17 . 1.397(5) ?
C16 H16 . 0.93 ?
C17 H17 . 0.93 ?
C18 N1 . 1.475(4) ?
C18 C19 . 1.522(5) ?
C18 H18A . 0.97 ?
C18 H18B . 0.97 ?
C19 H19A . 0.96 ?
C19 H19B . 0.96 ?
C19 H19C . 0.96 ?
C20 N2 . 1.469(4) ?
C20 C21 . 1.516(5) ?
C20 H20A . 0.97 ?
C20 H20B . 0.97 ?
C21 H21A . 0.96 ?
C21 H21B . 0.96 ?
C21 H21C . 0.96 ?

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
_geom_angle_publ_flag
C6 C1 C2 121.0(3) . . ?
C6 C1 N1 133.4(3) . . ?
C2 C1 N1 105.6(3) . . ?
C3 C2 O1 127.6(3) . . ?
C3 C2 C1 123.4(3) . . ?
O1 C2 C1 109.0(3) . . ?
C2 C3 C4 115.8(3) . . ?
C2 C3 H3 122.1 . . ?
C4 C3 H3 122.1 . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C6 C5 C4 122.4(3) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C1 C6 C5 116.2(3) . . ?
C1 C6 H6 121.9 . . ?
C5 C6 H6 121.9 . . ?
N1 C7 O1 110.1(3) . . ?
N1 C7 C8 127.2(3) . . ?
O1 C7 C8 122.7(3) . . ?
C7 C8 C9 124.8(3) . . ?
C7 C8 H8 117.6 . . ?
C9 C8 H8 117.6 . . ?
C10 C9 C8 121.1(3) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 125.2(3) . . ?
C9 C10 H10 117.4 . . ?
C11 C10 H10 117.4 . . ?
N2 C11 O2 110.0(3) . . ?
N2 C11 C10 126.5(3) . . ?
O2 C11 C10 123.5(3) . . ?
C13 C12 C17 121.6(3) . . ?
C13 C12 N2 105.8(3) . . ?
C17 C12 N2 132.6(3) . . ?
C14 C13 C12 123.3(3) . . ?
C14 C13 O2 127.9(3) . . ?
C12 C13 O2 108.8(3) . . ?
C13 C14 C15 115.5(3) . . ?
C13 C14 H14 122.3 . . ?
C15 C14 H14 122.3 . . ?
C16 C15 C14 122.0(3) . . ?
C16 C15 H15 119 . . ?
C14 C15 H15 119 . . ?
C17 C16 C15 121.7(3) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C12 C17 C16 116.0(3) . . ?
C12 C17 H17 122 . . ?
C16 C17 H17 122 . . ?
N1 C18 C19 112.6(3) . . ?
N1 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
N1 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 C21 111.3(3) . . ?
N2 C20 H20A 109.4 . . ?
C21 C20 H20A 109.4 . . ?
N2 C20 H20B 109.4 . . ?
C21 C20 H20B 109.4 . . ?
H20A C20 H20B 108 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C7 N1 C1 108.8(3) . . ?
C7 N1 C18 124.5(3) . . ?
C1 N1 C18 126.7(3) . . ?
C11 N2 C12 108.7(3) . . ?
C11 N2 C20 125.9(3) . . ?
C12 N2 C20 125.4(3) . . ?
C7 O1 C2 106.6(2) . . ?
C11 O2 C13 106.7(2) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.2(5) . . . . ?
N1 C1 C2 C3 -179.7(3) . . . . ?
C6 C1 C2 O1 -178.9(3) . . . . ?
N1 C1 C2 O1 0.2(3) . . . . ?
O1 C2 C3 C4 178.7(3) . . . . ?
C1 C2 C3 C4 -1.4(5) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C3 C4 C5 C6 1.1(5) . . . . ?
C2 C1 C6 C5 0.2(5) . . . . ?
N1 C1 C6 C5 -178.6(3) . . . . ?
C4 C5 C6 C1 -1.4(5) . . . . ?
N1 C7 C8 C9 -179.4(3) . . . . ?
O1 C7 C8 C9 -0.9(5) . . . . ?
C7 C8 C9 C10 176.5(3) . . . . ?
C8 C9 C10 C11 178.7(3) . . . . ?
C9 C10 C11 N2 -178.4(3) . . . . ?
C9 C10 C11 O2 2.1(5) . . . . ?
C17 C12 C13 C14 -0.2(5) . . . . ?
N2 C12 C13 C14 179.5(3) . . . . ?
C17 C12 C13 O2 179.8(3) . . . . ?
N2 C12 C13 O2 -0.5(3) . . . . ?
C12 C13 C14 C15 0.6(5) . . . . ?
O2 C13 C14 C15 -179.4(3) . . . . ?
C13 C14 C15 C16 -0.6(5) . . . . ?
C14 C15 C16 C17 0.2(5) . . . . ?
C13 C12 C17 C16 -0.2(4) . . . . ?
N2 C12 C17 C16 -179.8(3) . . . . ?
C15 C16 C17 C12 0.3(5) . . . . ?
O1 C7 N1 C1 -0.3(3) . . . . ?
C8 C7 N1 C1 178.3(3) . . . . ?
O1 C7 N1 C18 -177.0(3) . . . . ?
C8 C7 N1 C18 1.6(5) . . . . ?
C6 C1 N1 C7 179.1(3) . . . . ?
C2 C1 N1 C7 0.0(3) . . . . ?
C6 C1 N1 C18 -4.3(5) . . . . ?
C2 C1 N1 C18 176.7(3) . . . . ?
C19 C18 N1 C7 -80.4(4) . . . . ?
C19 C18 N1 C1 103.5(4) . . . . ?
O2 C11 N2 C12 -0.2(3) . . . . ?
C10 C11 N2 C12 -179.8(3) . . . . ?
O2 C11 N2 C20 177.4(3) . . . . ?
C10 C11 N2 C20 -2.1(5) . . . . ?
C13 C12 N2 C11 0.5(3) . . . . ?
C17 C12 N2 C11 -179.9(3) . . . . ?
C13 C12 N2 C20 -177.2(3) . . . . ?
C17 C12 N2 C20 2.4(5) . . . . ?
C21 C20 N2 C11 -90.8(4) . . . . ?
C21 C20 N2 C12 86.5(4) . . . . ?
N1 C7 O1 C2 0.5(3) . . . . ?
C8 C7 O1 C2 -178.2(3) . . . . ?
C3 C2 O1 C7 179.5(3) . . . . ?
C1 C2 O1 C7 -0.4(3) . . . . ?
N2 C11 O2 C13 -0.1(3) . . . . ?
C10 C11 O2 C13 179.5(3) . . . . ?
C14 C13 O2 C11 -179.6(3) . . . . ?
C12 C13 O2 C11 0.4(3) . . . . ?


# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_gppw5
_database_code_depnum_ccdc_archive 'CCDC 1420387'
_audit_update_record             
;
2015-08-24 deposited with the CCDC.
2016-03-18 downloaded from the CCDC.
;

_audit_creation_date             2014-02-28T12:23:39-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 3,3'-Diethylthiacarbocyanine iodide
;
_chemical_formula_moiety         'C21 H21 I1 N2 S2'
_chemical_formula_sum            'C23.75 H34.75 I N2 O2.75 S2'
_chemical_formula_analytical     ?
_chemical_formula_weight         583.31

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.429(5)
_cell_length_b                   18.273(5)
_cell_length_c                   15.316(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 113.767(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     4464(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6193
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      33.2
_cell_measurement_temperature    120(2)
_exptl_crystal_description       Prism
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.736
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2386
_exptl_absorpt_coefficient_mu    1.652
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'Higashi, 1995'
_exptl_absorpt_correction_T_min  0.679
_exptl_absorpt_correction_T_max  0.848

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_source                   'Sealed Tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
        Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            17402
_diffrn_reflns_av_R_equivalents  0.056
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.010 295 98 ' '
2 0.500 0.500 0.019 295 98 ' '
_platon_squeeze_details          
;
The unit cell contains 11 methanol molecules which have been treated as a 
diffuse contribution to the overall scattering without specific atom positions 
by SQUEEZE/PLATON.
;
_reflns_number_total             5105
_reflns_number_gt                4650
_reflns_threshold_expression     >2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.118
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_restrained_S_all      1.09
_refine_ls_number_reflns         5105
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0475P)²+12.8481P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.662
_refine_diff_density_min         -0.782
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
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 0 '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 0.006 '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'

_computing_data_collection       
;
        CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_cell_refinement       
;
        CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction        
;
        CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_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
_atom_site_type_symbol
C1 0.92613(19) 0.68912(19) 0.4507(2) 0.0343(7) Uani d . 1 . . C
C2 0.93870(19) 0.7635(2) 0.4442(3) 0.0371(7) Uani d . 1 . . C
C3 0.9574(2) 0.8099(2) 0.5223(3) 0.0494(10) Uani d . 1 . . C
H3 0.9646 0.8599 0.5175 0.059 Uiso calc R 1 . . H
C4 0.9647(2) 0.7783(3) 0.6078(3) 0.0600(13) Uani d . 1 . . C
H4 0.979 0.8074 0.6619 0.072 Uiso calc R 1 . . H
C5 0.9511(2) 0.7043(3) 0.6139(3) 0.0547(11) Uani d . 1 . . C
H5 0.9548 0.685 0.6716 0.066 Uiso calc R 1 . . H
C6 0.9321(2) 0.6584(2) 0.5361(2) 0.0429(8) Uani d . 1 . . C
H6 0.9236 0.6086 0.5409 0.051 Uiso calc R 1 . . H
C7 0.90283(18) 0.69625(17) 0.2907(2) 0.0291(6) Uani d . 1 . . C
C8 0.88325(19) 0.67280(17) 0.1980(2) 0.0307(6) Uani d . 1 . . C
H8 0.8752 0.6228 0.1862 0.037 Uiso calc R 1 . . H
C9 0.87466(18) 0.71731(17) 0.1218(2) 0.0305(6) Uani d . 1 . . C
H9 0.8829 0.7674 0.1321 0.037 Uiso calc R 1 . . H
C10 0.8542(2) 0.69025(18) 0.0304(2) 0.0326(6) Uani d . 1 . . C
H10 0.8487 0.6398 0.0224 0.039 Uiso calc R 1 . . H
C11 0.84120(19) 0.73232(17) -0.0503(2) 0.0312(6) Uani d . 1 . . C
C12 0.81326(19) 0.75692(18) -0.2086(2) 0.0314(6) Uani d . 1 . . C
C13 0.82332(18) 0.82761(17) -0.1729(2) 0.0301(6) Uani d . 1 . . C
C14 0.8185(2) 0.88775(19) -0.2306(3) 0.0378(7) Uani d . 1 . . C
H14 0.8273 0.935 -0.206 0.045 Uiso calc R 1 . . H
C15 0.8001(2) 0.8746(2) -0.3262(3) 0.0390(7) Uani d . 1 . . C
H15 0.7965 0.9138 -0.3664 0.047 Uiso calc R 1 . . H
C16 0.7871(2) 0.8042(2) -0.3628(2) 0.0381(7) Uani d . 1 . . C
H16 0.7739 0.7972 -0.4274 0.046 Uiso calc R 1 . . H
C17 0.7932(2) 0.7439(2) -0.3053(2) 0.0357(7) Uani d . 1 . . C
H17 0.7843 0.6967 -0.33 0.043 Uiso calc R 1 . . H
C18 0.8958(2) 0.57297(17) 0.3547(2) 0.0314(6) Uani d . 1 . . C
H18A 0.8556 0.5611 0.2909 0.038 Uiso calc R 1 . . H
H18B 0.8738 0.5552 0.3997 0.038 Uiso calc R 1 . . H
C19 0.9786(2) 0.53515(18) 0.3732(3) 0.0373(7) Uani d . 1 . . C
H19A 1.0026 0.5555 0.3321 0.056 Uiso calc R 1 . . H
H19B 0.9691 0.4837 0.3607 0.056 Uiso calc R 1 . . H
H19C 1.0164 0.5423 0.4386 0.056 Uiso calc R 1 . . H
C20 0.8251(2) 0.62490(18) -0.1551(2) 0.0367(7) Uani d . 1 . . C
H20A 0.8697 0.6022 -0.1012 0.044 Uiso calc R 1 . . H
H20B 0.8366 0.6168 -0.2113 0.044 Uiso calc R 1 . . H
C21 0.7424(2) 0.58903(19) -0.1695(3) 0.0452(9) Uani d . 1 . . C
H21A 0.7312 0.5963 -0.1137 0.068 Uiso calc R 1 . . H
H21B 0.7455 0.5375 -0.1802 0.068 Uiso calc R 1 . . H
H21C 0.6982 0.6105 -0.2238 0.068 Uiso calc R 1 . . H
N1 0.90621(16) 0.65288(14) 0.36413(18) 0.0302(5) Uani d . 1 . . N
N2 0.82432(17) 0.70426(14) -0.13785(19) 0.0312(5) Uani d . 1 . . N
S1 0.92658(5) 0.78679(4) 0.32846(6) 0.03610(19) Uani d . 1 . . S
S2 0.84237(5) 0.82757(4) -0.05154(6) 0.03103(17) Uani d . 1 . . S
I1 0.77385(2) 0.476347(13) 0.086939(19) 0.05768(13) Uani d . 1 . . I



#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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 C2 . 1.387(5) ?
C1 C6 . 1.388(5) ?
C1 N1 . 1.395(4) ?
C2 C3 . 1.394(5) ?
C2 S1 . 1.751(4) ?
C3 C4 . 1.389(7) ?
C3 H3 . 0.93 ?
C4 C5 . 1.382(7) ?
C4 H4 . 0.93 ?
C5 C6 . 1.384(6) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C7 N1 . 1.358(4) ?
C7 C8 . 1.388(4) ?
C7 S1 . 1.747(3) ?
C8 C9 . 1.380(4) ?
C8 H8 . 0.93 ?
C9 C10 . 1.389(5) ?
C9 H9 . 0.93 ?
C10 C11 . 1.394(4) ?
C10 H10 . 0.93 ?
C11 N2 . 1.353(4) ?
C11 S2 . 1.741(3) ?
C12 C13 . 1.386(5) ?
C12 C17 . 1.397(5) ?
C12 N2 . 1.403(4) ?
C13 C14 . 1.391(4) ?
C13 S2 . 1.751(3) ?
C14 C15 . 1.388(5) ?
C14 H14 . 0.93 ?
C15 C16 . 1.385(5) ?
C15 H15 . 0.93 ?
C16 C17 . 1.387(5) ?
C16 H16 . 0.93 ?
C17 H17 . 0.93 ?
C18 N1 . 1.471(4) ?
C18 C19 . 1.520(5) ?
C18 H18A . 0.97 ?
C18 H18B . 0.97 ?
C19 H19A . 0.96 ?
C19 H19B . 0.96 ?
C19 H19C . 0.96 ?
C20 N2 . 1.475(4) ?
C20 C21 . 1.516(5) ?
C20 H20A . 0.97 ?
C20 H20B . 0.97 ?
C21 H21A . 0.96 ?
C21 H21B . 0.96 ?
C21 H21C . 0.96 ?

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
_geom_angle_publ_flag
C2 C1 C6 120.7(3) . . ?
C2 C1 N1 112.5(3) . . ?
C6 C1 N1 126.8(3) . . ?
C1 C2 C3 121.5(4) . . ?
C1 C2 S1 110.7(3) . . ?
C3 C2 S1 127.8(3) . . ?
C4 C3 C2 117.3(4) . . ?
C4 C3 H3 121.4 . . ?
C2 C3 H3 121.4 . . ?
C5 C4 C3 121.1(4) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 121.5(4) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 117.8(4) . . ?
C5 C6 H6 121.1 . . ?
C1 C6 H6 121.1 . . ?
N1 C7 C8 125.3(3) . . ?
N1 C7 S1 110.7(2) . . ?
C8 C7 S1 124.0(2) . . ?
C9 C8 C7 125.5(3) . . ?
C9 C8 H8 117.2 . . ?
C7 C8 H8 117.2 . . ?
C8 C9 C10 122.6(3) . . ?
C8 C9 H9 118.7 . . ?
C10 C9 H9 118.7 . . ?
C9 C10 C11 125.5(3) . . ?
C9 C10 H10 117.2 . . ?
C11 C10 H10 117.2 . . ?
N2 C11 C10 124.2(3) . . ?
N2 C11 S2 111.5(2) . . ?
C10 C11 S2 124.3(3) . . ?
C13 C12 C17 121.0(3) . . ?
C13 C12 N2 112.2(3) . . ?
C17 C12 N2 126.8(3) . . ?
C12 C13 C14 121.3(3) . . ?
C12 C13 S2 111.0(2) . . ?
C14 C13 S2 127.7(3) . . ?
C15 C14 C13 117.6(3) . . ?
C15 C14 H14 121.2 . . ?
C13 C14 H14 121.2 . . ?
C16 C15 C14 121.2(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 121.4(3) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C16 C17 C12 117.4(3) . . ?
C16 C17 H17 121.3 . . ?
C12 C17 H17 121.3 . . ?
N1 C18 C19 111.2(3) . . ?
N1 C18 H18A 109.4 . . ?
C19 C18 H18A 109.4 . . ?
N1 C18 H18B 109.4 . . ?
C19 C18 H18B 109.4 . . ?
H18A C18 H18B 108 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 C21 112.0(3) . . ?
N2 C20 H20A 109.2 . . ?
C21 C20 H20A 109.2 . . ?
N2 C20 H20B 109.2 . . ?
C21 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C7 N1 C1 114.9(3) . . ?
C7 N1 C18 122.4(3) . . ?
C1 N1 C18 122.5(3) . . ?
C11 N2 C12 114.4(3) . . ?
C11 N2 C20 122.4(3) . . ?
C12 N2 C20 123.0(3) . . ?
C7 S1 C2 91.20(16) . . ?
C11 S2 C13 90.82(15) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.2(5) . . . . ?
N1 C1 C2 C3 178.5(3) . . . . ?
C6 C1 C2 S1 -179.6(3) . . . . ?
N1 C1 C2 S1 -0.8(3) . . . . ?
C1 C2 C3 C4 1.4(5) . . . . ?
S1 C2 C3 C4 -179.4(3) . . . . ?
C2 C3 C4 C5 -2.2(5) . . . . ?
C3 C4 C5 C6 1.9(6) . . . . ?
C4 C5 C6 C1 -0.7(5) . . . . ?
C2 C1 C6 C5 -0.1(5) . . . . ?
N1 C1 C6 C5 -178.7(3) . . . . ?
N1 C7 C8 C9 175.7(3) . . . . ?
S1 C7 C8 C9 -4.2(5) . . . . ?
C7 C8 C9 C10 -179.4(3) . . . . ?
C8 C9 C10 C11 177.2(3) . . . . ?
C9 C10 C11 N2 177.5(3) . . . . ?
C9 C10 C11 S2 -4.0(5) . . . . ?
C17 C12 C13 C14 -3.7(5) . . . . ?
N2 C12 C13 C14 177.2(3) . . . . ?
C17 C12 C13 S2 176.7(2) . . . . ?
N2 C12 C13 S2 -2.4(3) . . . . ?
C12 C13 C14 C15 2.4(5) . . . . ?
S2 C13 C14 C15 -178.1(3) . . . . ?
C13 C14 C15 C16 0.0(5) . . . . ?
C14 C15 C16 C17 -1.1(5) . . . . ?
C15 C16 C17 C12 -0.2(5) . . . . ?
C13 C12 C17 C16 2.5(5) . . . . ?
N2 C12 C17 C16 -178.5(3) . . . . ?
C8 C7 N1 C1 -179.1(3) . . . . ?
S1 C7 N1 C1 0.8(3) . . . . ?
C8 C7 N1 C18 5.2(5) . . . . ?
S1 C7 N1 C18 -174.9(2) . . . . ?
C2 C1 N1 C7 0.0(4) . . . . ?
C6 C1 N1 C7 178.7(3) . . . . ?
C2 C1 N1 C18 175.7(3) . . . . ?
C6 C1 N1 C18 -5.6(5) . . . . ?
C19 C18 N1 C7 86.1(4) . . . . ?
C19 C18 N1 C1 -89.3(4) . . . . ?
C10 C11 N2 C12 179.8(3) . . . . ?
S2 C11 N2 C12 1.1(3) . . . . ?
C10 C11 N2 C20 -5.4(5) . . . . ?
S2 C11 N2 C20 175.9(2) . . . . ?
C13 C12 N2 C11 0.9(4) . . . . ?
C17 C12 N2 C11 -178.2(3) . . . . ?
C13 C12 N2 C20 -173.9(3) . . . . ?
C17 C12 N2 C20 7.0(5) . . . . ?
C21 C20 N2 C11 84.2(4) . . . . ?
C21 C20 N2 C12 -101.4(4) . . . . ?
N1 C7 S1 C2 -1.1(2) . . . . ?
C8 C7 S1 C2 178.9(3) . . . . ?
C1 C2 S1 C7 1.1(2) . . . . ?
C3 C2 S1 C7 -178.2(3) . . . . ?
N2 C11 S2 C13 -2.1(2) . . . . ?
C10 C11 S2 C13 179.2(3) . . . . ?
C12 C13 S2 C11 2.6(2) . . . . ?
C14 C13 S2 C11 -177.0(3) . . . . ?


# start Validation Reply Form
_vrf_CHEMW03_I                   
;
PROBLEM: ALERT: The ratio of given/expected molecular weight as
 calculated from the _atom_site* data lies outside
            the range 0.90 <> 1.10
RESPONSE: This discrepency is due to the treatment of disordered solvent 
molecules using SQUEEZE/PLATON (see _refine_special_details).
;
_vrf_PLAT043_I                   
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..      90.87 Check 
RESPONSE: This discrepency is due to the treatment of disordered solvent 
molecules using SQUEEZE/PLATON (see _refine_special_details).
;
_vrf_PLAT044_I                   
;
PROBLEM: Calculated and Reported Density Dx  Differ by ..     0.2706 Check 
RESPONSE: This discrepency is due to the treatment of disordered solvent 
molecules using SQUEEZE/PLATON (see _refine_special_details).
;
_vrf_PLAT601_I                   
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of .        297 Ang3  
RESPONSE: These voids contain disordered solvent molecules which have been 
treated as a diffuse contribution to the overall scattering using 
SQUEEZE/PLATON.
;
# end Validation Reply Form
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_gppw4
_database_code_depnum_ccdc_archive 'CCDC 1420388'
_audit_update_record             
;
2015-08-24 deposited with the CCDC.
2016-03-18 downloaded from the CCDC.
;

_audit_creation_date             2014-02-28T13:39:33-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 3,3'-Diethylthiatricarbocyanine iodide
;
_chemical_formula_moiety         'C25 H25 N2 S2, I1'
_chemical_formula_sum            'C25 H25 I1 N2 S2'
_chemical_formula_analytical     ?
_chemical_formula_weight         544.49

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.457(3)
_cell_length_b                   18.079(6)
_cell_length_c                   17.791(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.896(5)
_cell_angle_gamma                90
_cell_volume                     2347.0(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7548
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      32.9
_cell_measurement_temperature    120(2)
_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1096
_exptl_absorpt_coefficient_mu    1.557
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'Higashi, 1995'
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_T_max  0.817

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
        Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            15528
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.053
_diffrn_reflns_theta_min         2.6
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total             5228
_reflns_number_gt                4597
_reflns_threshold_expression     >2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1282
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_refine_ls_number_reflns         5228
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0509P)²+5.5903P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.427
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.136
_refine_ls_extinction_method     none
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 0 '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'
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'

_computing_data_collection       
;
        CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_cell_refinement       
;
        CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction        
;
        CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_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
_atom_site_type_symbol
C1 -0.2418(5) 1.2136(2) 0.0740(3) 0.0259(8) Uani d . 1 . . C
C2 -0.1460(6) 1.2624(2) 0.1294(3) 0.0268(8) Uani d . 1 . . C
C3 -0.1026(6) 1.3342(2) 0.1100(3) 0.0314(9) Uani d . 1 . . C
H3 -0.0387 1.3665 0.1467 0.038 Uiso calc R 1 . . H
C4 -0.1584(6) 1.3553(3) 0.0341(3) 0.0337(10) Uani d . 1 . . C
H4 -0.1316 1.4028 0.0196 0.04 Uiso calc R 1 . . H
C5 -0.2543(6) 1.3069(3) -0.0214(3) 0.0327(9) Uani d . 1 . . C
H5 -0.2895 1.3228 -0.072 0.039 Uiso calc R 1 . . H
C6 -0.2978(6) 1.2357(2) -0.0022(3) 0.0294(9) Uani d . 1 . . C
H6 -0.3623 1.2037 -0.039 0.035 Uiso calc R 1 . . H
C7 -0.1806(5) 1.1351(2) 0.1794(3) 0.0256(8) Uani d . 1 . . C
C8 -0.1709(6) 1.0686(2) 0.2201(3) 0.0282(9) Uani d . 1 . . C
H8 -0.2427 1.0292 0.1978 0.034 Uiso calc R 1 . . H
C9 -0.0602(6) 1.0583(2) 0.2921(3) 0.0288(9) Uani d . 1 . . C
H9 0.0076 1.0985 0.3151 0.035 Uiso calc R 1 . . H
C10 -0.0439(6) 0.9913(2) 0.3322(3) 0.0277(9) Uani d . 1 . . C
H10 -0.115 0.9512 0.3111 0.033 Uiso calc R 1 . . H
C11 0.0752(6) 0.9829(2) 0.4026(3) 0.0284(9) Uani d . 1 . . C
H11 0.1403 1.0247 0.4228 0.034 Uiso calc R 1 . . H
C12 0.1076(6) 0.9186(2) 0.4460(3) 0.0284(9) Uani d . 1 . . C
H12 0.0439 0.876 0.4273 0.034 Uiso calc R 1 . . H
C13 0.2308(6) 0.9150(2) 0.5162(3) 0.0275(9) Uani d . 1 . . C
H13 0.2912 0.9585 0.5343 0.033 Uiso calc R 1 . . H
C14 0.2719(6) 0.8517(2) 0.5620(2) 0.0271(8) Uani d . 1 . . C
H14 0.2127 0.8079 0.5443 0.033 Uiso calc R 1 . . H
C15 0.3951(5) 0.8501(2) 0.6320(3) 0.0258(8) Uani d . 1 . . C
C17 0.6093(6) 0.8773(2) 0.7573(2) 0.0273(9) Uani d . 1 . . C
C18 0.7191(6) 0.9029(2) 0.8250(3) 0.0297(9) Uani d . 1 . . C
H18 0.7586 0.9518 0.8299 0.036 Uiso calc R 1 . . H
C19 0.7678(6) 0.8531(3) 0.8850(3) 0.0303(9) Uani d . 1 . . C
H19 0.8387 0.8692 0.9313 0.036 Uiso calc R 1 . . H
C20 0.7127(6) 0.7794(3) 0.8772(3) 0.0304(9) Uani d . 1 . . C
H20 0.7494 0.747 0.918 0.036 Uiso calc R 1 . . H
C21 0.6038(6) 0.7535(2) 0.8095(3) 0.0299(9) Uani d . 1 . . C
H21 0.5681 0.7042 0.804 0.036 Uiso calc R 1 . . H
C22 0.5501(5) 0.8037(2) 0.7502(2) 0.0257(8) Uani d . 1 . . C
C23 -0.3485(6) 1.0809(2) 0.0565(3) 0.0268(8) Uani d . 1 . . C
H23A -0.4388 1.0997 0.0135 0.032 Uiso calc R 1 . . H
H23B -0.4111 1.0491 0.0867 0.032 Uiso calc R 1 . . H
C24 -0.2059(6) 1.0364(2) 0.0265(3) 0.0312(9) Uani d . 1 . . C
H24A -0.1481 1.0672 -0.0055 0.047 Uiso calc R 1 . . H
H24B -0.264 0.9952 -0.0029 0.047 Uiso calc R 1 . . H
H24C -0.1154 1.0185 0.069 0.047 Uiso calc R 1 . . H
C25 0.3448(6) 0.7183(2) 0.6576(3) 0.0273(8) Uani d . 1 . . C
H25A 0.2185 0.7263 0.6317 0.033 Uiso calc R 1 . . H
H25B 0.3438 0.6902 0.704 0.033 Uiso calc R 1 . . H
C26 0.4411(7) 0.6730(3) 0.6055(3) 0.0381(11) Uani d . 1 . . C
H26A 0.4492 0.7016 0.5608 0.057 Uiso calc R 1 . . H
H26B 0.3726 0.6287 0.59 0.057 Uiso calc R 1 . . H
H26C 0.5621 0.6603 0.6327 0.057 Uiso calc R 1 . . H
I1 -0.46636(4) 1.097302(15) -0.179870(18) 0.03296(12) Uani d . 1 . . I
N1 -0.2634(5) 1.14352(19) 0.1044(2) 0.0246(7) Uani d . 1 . . N
N2 0.4319(5) 0.7904(2) 0.6790(2) 0.0257(7) Uani d . 1 . . N
S1 -0.08254(14) 1.21800(6) 0.21838(6) 0.0267(2) Uani d . 1 . . S
S2 0.51894(15) 0.92791(6) 0.67357(6) 0.0276(2) Uani d . 1 . . S



#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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 C6 . 1.391(6) ?
C1 N1 . 1.401(5) ?
C1 C2 . 1.404(6) ?
C2 C3 . 1.399(6) ?
C2 S1 . 1.750(5) ?
C3 C4 . 1.382(7) ?
C3 H3 . 0.93 ?
C4 C5 . 1.401(7) ?
C4 H4 . 0.93 ?
C5 C6 . 1.388(6) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C7 N1 . 1.357(6) ?
C7 C8 . 1.398(6) ?
C7 S1 . 1.747(4) ?
C8 C9 . 1.385(6) ?
C8 H8 . 0.93 ?
C9 C10 . 1.399(6) ?
C9 H9 . 0.93 ?
C10 C11 . 1.386(6) ?
C10 H10 . 0.93 ?
C11 C12 . 1.390(6) ?
C11 H11 . 0.93 ?
C12 C13 . 1.390(6) ?
C12 H12 . 0.93 ?
C13 C14 . 1.402(6) ?
C13 H13 . 0.93 ?
C14 C15 . 1.386(6) ?
C14 H14 . 0.93 ?
C15 N2 . 1.359(6) ?
C15 S2 . 1.759(4) ?
C17 C18 . 1.388(6) ?
C17 C22 . 1.399(6) ?
C17 S2 . 1.760(4) ?
C18 C19 . 1.387(7) ?
C18 H18 . 0.93 ?
C19 C20 . 1.393(6) ?
C19 H19 . 0.93 ?
C20 C21 . 1.387(6) ?
C20 H20 . 0.93 ?
C21 C22 . 1.387(6) ?
C21 H21 . 0.93 ?
C22 N2 . 1.406(5) ?
C23 N1 . 1.480(5) ?
C23 C24 . 1.515(6) ?
C23 H23A . 0.97 ?
C23 H23B . 0.97 ?
C24 H24A . 0.96 ?
C24 H24B . 0.96 ?
C24 H24C . 0.96 ?
C25 N2 . 1.472(5) ?
C25 C26 . 1.523(6) ?
C25 H25A . 0.97 ?
C25 H25B . 0.97 ?
C26 H26A . 0.96 ?
C26 H26B . 0.96 ?
C26 H26C . 0.96 ?

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
_geom_angle_publ_flag
C6 C1 N1 126.9(4) . . ?
C6 C1 C2 120.8(4) . . ?
N1 C1 C2 112.2(4) . . ?
C3 C2 C1 121.3(4) . . ?
C3 C2 S1 128.0(4) . . ?
C1 C2 S1 110.6(3) . . ?
C4 C3 C2 117.3(4) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C3 C4 C5 121.6(4) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 121.2(4) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 117.9(4) . . ?
C5 C6 H6 121.1 . . ?
C1 C6 H6 121.1 . . ?
N1 C7 C8 124.8(4) . . ?
N1 C7 S1 111.3(3) . . ?
C8 C7 S1 124.0(3) . . ?
C9 C8 C7 123.5(4) . . ?
C9 C8 H8 118.2 . . ?
C7 C8 H8 118.2 . . ?
C8 C9 C10 124.1(4) . . ?
C8 C9 H9 117.9 . . ?
C10 C9 H9 117.9 . . ?
C11 C10 C9 121.9(4) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 126.8(4) . . ?
C10 C11 H11 116.6 . . ?
C12 C11 H11 116.6 . . ?
C11 C12 C13 123.0(4) . . ?
C11 C12 H12 118.5 . . ?
C13 C12 H12 118.5 . . ?
C12 C13 C14 125.8(4) . . ?
C12 C13 H13 117.1 . . ?
C14 C13 H13 117.1 . . ?
C15 C14 C13 124.3(4) . . ?
C15 C14 H14 117.8 . . ?
C13 C14 H14 117.8 . . ?
N2 C15 C14 125.5(4) . . ?
N2 C15 S2 110.7(3) . . ?
C14 C15 S2 123.7(3) . . ?
C18 C17 C22 121.0(4) . . ?
C18 C17 S2 127.9(4) . . ?
C22 C17 S2 111.0(3) . . ?
C19 C18 C17 117.7(4) . . ?
C19 C18 H18 121.2 . . ?
C17 C18 H18 121.2 . . ?
C18 C19 C20 121.3(4) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C21 C20 C19 121.1(4) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C22 C21 C20 117.7(4) . . ?
C22 C21 H21 121.1 . . ?
C20 C21 H21 121.1 . . ?
C21 C22 C17 121.1(4) . . ?
C21 C22 N2 127.0(4) . . ?
C17 C22 N2 111.8(4) . . ?
N1 C23 C24 111.2(3) . . ?
N1 C23 H23A 109.4 . . ?
C24 C23 H23A 109.4 . . ?
N1 C23 H23B 109.4 . . ?
C24 C23 H23B 109.4 . . ?
H23A C23 H23B 108 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N2 C25 C26 113.3(4) . . ?
N2 C25 H25A 108.9 . . ?
C26 C25 H25A 108.9 . . ?
N2 C25 H25B 108.9 . . ?
C26 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C7 N1 C1 114.6(4) . . ?
C7 N1 C23 122.4(3) . . ?
C1 N1 C23 122.6(4) . . ?
C15 N2 C22 115.3(4) . . ?
C15 N2 C25 121.5(4) . . ?
C22 N2 C25 123.1(4) . . ?
C7 S1 C2 91.2(2) . . ?
C15 S2 C17 91.0(2) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.4(6) . . . . ?
N1 C1 C2 C3 177.1(4) . . . . ?
C6 C1 C2 S1 -176.6(3) . . . . ?
N1 C1 C2 S1 0.9(4) . . . . ?
C1 C2 C3 C4 0.2(6) . . . . ?
S1 C2 C3 C4 175.7(3) . . . . ?
C2 C3 C4 C5 -0.1(7) . . . . ?
C3 C4 C5 C6 0.2(7) . . . . ?
C4 C5 C6 C1 -0.5(6) . . . . ?
N1 C1 C6 C5 -176.6(4) . . . . ?
C2 C1 C6 C5 0.6(6) . . . . ?
N1 C7 C8 C9 168.6(4) . . . . ?
S1 C7 C8 C9 -10.0(6) . . . . ?
C7 C8 C9 C10 -177.4(4) . . . . ?
C8 C9 C10 C11 177.0(4) . . . . ?
C9 C10 C11 C12 -177.5(4) . . . . ?
C10 C11 C12 C13 179.6(4) . . . . ?
C11 C12 C13 C14 -178.8(4) . . . . ?
C12 C13 C14 C15 -179.7(4) . . . . ?
C13 C14 C15 N2 177.1(4) . . . . ?
C13 C14 C15 S2 -0.1(6) . . . . ?
C22 C17 C18 C19 0.0(6) . . . . ?
S2 C17 C18 C19 177.3(3) . . . . ?
C17 C18 C19 C20 1.6(6) . . . . ?
C18 C19 C20 C21 -1.3(7) . . . . ?
C19 C20 C21 C22 -0.7(6) . . . . ?
C20 C21 C22 C17 2.3(6) . . . . ?
C20 C21 C22 N2 -175.9(4) . . . . ?
C18 C17 C22 C21 -2.0(6) . . . . ?
S2 C17 C22 C21 -179.8(3) . . . . ?
C18 C17 C22 N2 176.5(4) . . . . ?
S2 C17 C22 N2 -1.3(4) . . . . ?
C8 C7 N1 C1 -174.6(4) . . . . ?
S1 C7 N1 C1 4.1(4) . . . . ?
C8 C7 N1 C23 -2.2(6) . . . . ?
S1 C7 N1 C23 176.6(3) . . . . ?
C6 C1 N1 C7 174.1(4) . . . . ?
C2 C1 N1 C7 -3.3(5) . . . . ?
C6 C1 N1 C23 1.6(6) . . . . ?
C2 C1 N1 C23 -175.7(3) . . . . ?
C24 C23 N1 C7 -81.4(5) . . . . ?
C24 C23 N1 C1 90.4(5) . . . . ?
C14 C15 N2 C22 -174.7(4) . . . . ?
S2 C15 N2 C22 2.8(4) . . . . ?
C14 C15 N2 C25 2.2(6) . . . . ?
S2 C15 N2 C25 179.7(3) . . . . ?
C21 C22 N2 C15 177.4(4) . . . . ?
C17 C22 N2 C15 -1.0(5) . . . . ?
C21 C22 N2 C25 0.5(6) . . . . ?
C17 C22 N2 C25 -177.9(4) . . . . ?
C26 C25 N2 C15 83.1(5) . . . . ?
C26 C25 N2 C22 -100.3(5) . . . . ?
N1 C7 S1 C2 -3.0(3) . . . . ?
C8 C7 S1 C2 175.8(4) . . . . ?
C3 C2 S1 C7 -174.7(4) . . . . ?
C1 C2 S1 C7 1.2(3) . . . . ?
N2 C15 S2 C17 -2.9(3) . . . . ?
C14 C15 S2 C17 174.6(4) . . . . ?
C18 C17 S2 C15 -175.2(4) . . . . ?
C22 C17 S2 C15 2.4(3) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p21oncmore
_database_code_depnum_ccdc_archive 'CCDC 1420389'
_audit_update_record             
;
2015-08-24 deposited with the CCDC.
2016-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H25 I N2 O S2'
_chemical_formula_weight         536.47

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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'

_cell_length_a                   21.150(4)
_cell_length_b                   6.4590(13)
_cell_length_c                   17.453(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.13(3)
_cell_angle_gamma                90.00
_cell_volume                     2380.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8005
_cell_measurement_theta_min      1.1
_cell_measurement_theta_max      33.07

_exptl_crystal_description       block
_exptl_crystal_colour            dark-coloured
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    1.537
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'Higashi, 1995'
_exptl_absorpt_correction_T_min  0.637
_exptl_absorpt_correction_T_max  0.735

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku CCD diffractometer with Saturn 724+'
_diffrn_measurement_method       'profile data from ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            21284
_diffrn_reflns_av_R_equivalents  0.1162
_diffrn_reflns_av_sigmaI/netI    0.1113
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         33.07
_reflns_number_total             8005
_reflns_number_gt                5309
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
        CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_cell_refinement       
;
        CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction        
;
        CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL-PLUS (Sheldrick, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1463P)²+33.0923P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0085(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8005
_refine_ls_number_parameters     285
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1989
_refine_ls_R_factor_gt           0.1573
_refine_ls_wR_factor_ref         0.4065
_refine_ls_wR_factor_gt          0.3702
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
I1 I 0.22625(4) 0.87045(13) 0.08839(5) 0.0515(3) Uani 0.978(8) 1 d P A 1
I1A I 0.3005(12) 0.869(2) 0.0883(7) 0.092(9) Uani 0.074(6) 1 d P B 2
I1B I 0.1386(19) 0.858(7) 0.087(2) 0.041(14) Uiso 0.016(4) 1 d P C 3
S2 S 0.33657(14) 0.2091(5) -0.27787(17) 0.0442(7) Uani 1 1 d . . .
S3 S 0.15603(14) 1.3011(5) -0.25454(18) 0.0458(7) Uani 1 1 d . . .
N1 N 0.1340(4) 1.3727(15) -0.1125(6) 0.044(2) Uani 1 1 d . . .
C23 C 0.2548(5) 0.7314(18) -0.1392(6) 0.040(2) Uani 1 1 d . . .
H23A H 0.2565 0.7230 -0.0860 0.048 Uiso 1 1 calc R . .
N2 N 0.3770(5) 0.0874(17) -0.1433(6) 0.047(2) Uani 1 1 d . . .
C21 C 0.1949(6) 1.048(2) -0.1305(7) 0.048(3) Uani 1 1 d . . .
H21A H 0.1970 1.0255 -0.0777 0.058 Uiso 1 1 calc R . .
C20 C 0.1039(6) 1.5366(19) -0.1543(8) 0.048(3) Uani 1 1 d . . .
C19 C 0.2834(5) 0.5760(17) -0.1791(7) 0.040(2) Uani 1 1 d . . .
H19A H 0.2816 0.5801 -0.2325 0.048 Uiso 1 1 calc R . .
C18 C 0.3816(5) -0.0217(18) -0.2701(7) 0.041(2) Uani 1 1 d . . .
C17 C 0.1354(6) 1.3625(18) -0.0272(7) 0.048(3) Uani 1 1 d . . .
H17A H 0.1364 1.5017 -0.0063 0.058 Uiso 1 1 calc R . .
H17B H 0.1735 1.2915 -0.0083 0.058 Uiso 1 1 calc R . .
C16 C 0.2228(5) 0.9042(16) -0.1744(7) 0.038(2) Uani 1 1 d . . .
H16A H 0.2210 0.9185 -0.2275 0.046 Uiso 1 1 calc R . .
C15 C 0.3969(6) -0.157(2) -0.3279(9) 0.054(3) Uani 1 1 d . . .
H15A H 0.3827 -0.1361 -0.3787 0.065 Uiso 1 1 calc R . .
C14 C 0.3419(4) 0.2414(17) -0.1786(6) 0.037(2) Uani 1 1 d . . .
C13 C 0.1628(5) 1.2296(17) -0.1574(7) 0.041(2) Uani 1 1 d . . .
C12 C 0.3830(6) 0.075(2) -0.0572(7) 0.049(3) Uani 1 1 d . . .
H12A H 0.3913 -0.0671 -0.0416 0.059 Uiso 1 1 calc R . .
H12B H 0.3436 0.1180 -0.0362 0.059 Uiso 1 1 calc R . .
C11 C 0.4540(6) -0.3636(19) -0.2317(10) 0.056(3) Uani 1 1 d . . .
H11A H 0.4791 -0.4785 -0.2198 0.067 Uiso 1 1 calc R . .
C10 C 0.0432(6) 1.8485(19) -0.1723(9) 0.053(3) Uani 1 1 d . . .
H10A H 0.0205 1.9582 -0.1528 0.063 Uiso 1 1 calc R . .
C9 C 0.3149(4) 0.4137(17) -0.1414(6) 0.039(2) Uani 1 1 d . . .
H9A H 0.3187 0.4179 -0.0881 0.047 Uiso 1 1 calc R . .
C8 C 0.3994(5) -0.0631(18) -0.1909(7) 0.043(2) Uani 1 1 d . . .
C7 C 0.4372(6) -0.236(2) -0.1735(8) 0.054(3) Uani 1 1 d . . .
H7A H 0.4508 -0.2643 -0.1230 0.065 Uiso 1 1 calc R . .
C6 C 0.0515(5) 1.8345(16) -0.2507(8) 0.046(3) Uani 1 1 d . . .
H6A H 0.0335 1.9344 -0.2835 0.055 Uiso 1 1 calc R . .
C4 C 0.1126(5) 1.5210(19) -0.2320(7) 0.043(2) Uani 1 1 d . . .
C3 C 0.4356(7) -0.329(2) -0.3052(9) 0.056(3) Uani 1 1 d . . .
H3A H 0.4485 -0.4198 -0.3425 0.067 Uiso 1 1 calc R . .
C2 C 0.0690(6) 1.6973(19) -0.1234(9) 0.053(3) Uani 1 1 d . . .
H2A H 0.0632 1.7028 -0.0710 0.064 Uiso 1 1 calc R . .
C1 C 0.0871(6) 1.671(2) -0.2816(10) 0.057(3) Uani 1 1 d . . .
H1A H 0.0931 1.6637 -0.3339 0.069 Uiso 1 1 calc R . .
C31 C 0.4371(7) 0.214(3) -0.0255(10) 0.065(4) Uani 1 1 d . . .
H31A H 0.4409 0.2024 0.0293 0.098 Uiso 1 1 calc R . .
H31B H 0.4281 0.3556 -0.0394 0.098 Uiso 1 1 calc R . .
H31C H 0.4760 0.1724 -0.0467 0.098 Uiso 1 1 calc R . .
C30 C 0.0770(7) 1.247(3) -0.0004(9) 0.068(4) Uani 1 1 d . . .
H30A H 0.0787 1.2431 0.0547 0.102 Uiso 1 1 calc R . .
H30B H 0.0766 1.1088 -0.0202 0.102 Uiso 1 1 calc R . .
H30C H 0.0393 1.3184 -0.0188 0.102 Uiso 1 1 calc R . .
O1 O 0.2995(5) 0.1239(17) -0.4485(5) 0.061(3) Uani 1 1 d D . .
H1O H 0.263(6) 0.08(3) -0.419(9) 0.070 Uiso 1 1 d D . .
H2O H 0.344(6) 0.08(3) -0.449(10) 0.070 Uiso 1 1 d D . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2 C14 1.743(11) . ?
S2 C18 1.770(11) . ?
S3 C4 1.748(13) . ?
S3 C13 1.756(13) . ?
N1 C13 1.375(14) . ?
N1 C20 1.416(14) . ?
N1 C17 1.489(16) . ?
C23 C19 1.380(16) . ?
C23 C16 1.426(14) . ?
C23 H23A 0.9300 . ?
N2 C14 1.369(14) . ?
N2 C8 1.380(16) . ?
N2 C12 1.503(16) . ?
C21 C16 1.360(16) . ?
C21 C13 1.422(17) . ?
C21 H21A 0.9300 . ?
C20 C4 1.381(18) . ?
C20 C2 1.400(18) . ?
C19 C9 1.389(16) . ?
C19 H19A 0.9300 . ?
C18 C15 1.385(18) . ?
C18 C8 1.437(17) . ?
C17 C30 1.54(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C16 H16A 0.9300 . ?
C15 C3 1.425(18) . ?
C15 H15A 0.9300 . ?
C14 C9 1.423(14) . ?
C12 C31 1.534(19) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C11 C3 1.34(2) . ?
C11 C7 1.37(2) . ?
C11 H11A 0.9300 . ?
C10 C2 1.389(18) . ?
C10 C6 1.39(2) . ?
C10 H10A 0.9300 . ?
C9 H9A 0.9300 . ?
C8 C7 1.398(19) . ?
C7 H7A 0.9300 . ?
C6 C1 1.422(18) . ?
C6 H6A 0.9300 . ?
C4 C1 1.387(19) . ?
C3 H3A 0.9300 . ?
C2 H2A 0.9300 . ?
C1 H1A 0.9300 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
O1 H1O 0.99(12) . ?
O1 H2O 0.99(12) . ?

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
_geom_angle_publ_flag
C14 S2 C18 91.1(5) . . ?
C4 S3 C13 90.7(5) . . ?
C13 N1 C20 114.2(11) . . ?
C13 N1 C17 123.6(10) . . ?
C20 N1 C17 122.2(10) . . ?
C19 C23 C16 124.3(11) . . ?
C19 C23 H23A 117.9 . . ?
C16 C23 H23A 117.9 . . ?
C14 N2 C8 115.9(10) . . ?
C14 N2 C12 120.2(10) . . ?
C8 N2 C12 123.5(10) . . ?
C16 C21 C13 126.2(11) . . ?
C16 C21 H21A 116.9 . . ?
C13 C21 H21A 116.9 . . ?
C4 C20 C2 122.3(12) . . ?
C4 C20 N1 111.8(11) . . ?
C2 C20 N1 125.9(12) . . ?
C23 C19 C9 121.5(10) . . ?
C23 C19 H19A 119.2 . . ?
C9 C19 H19A 119.2 . . ?
C15 C18 C8 121.6(11) . . ?
C15 C18 S2 128.3(10) . . ?
C8 C18 S2 110.0(8) . . ?
N1 C17 C30 110.7(11) . . ?
N1 C17 H17A 109.5 . . ?
C30 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
C30 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C21 C16 C23 120.2(11) . . ?
C21 C16 H16A 119.9 . . ?
C23 C16 H16A 119.9 . . ?
C18 C15 C3 116.2(14) . . ?
C18 C15 H15A 121.9 . . ?
C3 C15 H15A 121.9 . . ?
N2 C14 C9 125.8(11) . . ?
N2 C14 S2 111.4(8) . . ?
C9 C14 S2 122.8(8) . . ?
N1 C13 C21 125.8(11) . . ?
N1 C13 S3 111.0(9) . . ?
C21 C13 S3 123.2(9) . . ?
N2 C12 C31 110.4(12) . . ?
N2 C12 H12A 109.6 . . ?
C31 C12 H12A 109.6 . . ?
N2 C12 H12B 109.6 . . ?
C31 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C3 C11 C7 122.4(13) . . ?
C3 C11 H11A 118.8 . . ?
C7 C11 H11A 118.8 . . ?
C2 C10 C6 119.4(12) . . ?
C2 C10 H10A 120.3 . . ?
C6 C10 H10A 120.3 . . ?
C19 C9 C14 124.6(10) . . ?
C19 C9 H9A 117.7 . . ?
C14 C9 H9A 117.7 . . ?
N2 C8 C7 130.0(12) . . ?
N2 C8 C18 111.6(10) . . ?
C7 C8 C18 118.3(12) . . ?
C11 C7 C8 119.2(14) . . ?
C11 C7 H7A 120.4 . . ?
C8 C7 H7A 120.4 . . ?
C10 C6 C1 121.3(12) . . ?
C10 C6 H6A 119.4 . . ?
C1 C6 H6A 119.4 . . ?
C20 C4 C1 119.6(12) . . ?
C20 C4 S3 112.3(9) . . ?
C1 C4 S3 128.1(10) . . ?
C11 C3 C15 122.0(13) . . ?
C11 C3 H3A 119.0 . . ?
C15 C3 H3A 119.0 . . ?
C10 C2 C20 118.9(14) . . ?
C10 C2 H2A 120.6 . . ?
C20 C2 H2A 120.6 . . ?
C4 C1 C6 118.6(14) . . ?
C4 C1 H1A 120.7 . . ?
C6 C1 H1A 120.7 . . ?
C12 C31 H31A 109.5 . . ?
C12 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C12 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C17 C30 H30A 109.5 . . ?
C17 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C17 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
H1O O1 H2O 134(10) . . ?

_diffrn_measured_fraction_theta_max 0.887
_diffrn_reflns_theta_full        33.07
_diffrn_measured_fraction_theta_full 0.887
_refine_diff_density_max         1.617
_refine_diff_density_min         -2.194
_refine_diff_density_rms         0.221

_vrf_PLAT029_I                   
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.887 Note  
RESPONSE: Noted. There is disorder in the structure, which compromises
recorded data intensity (heavily as the heavy present (iodine) is the 
subject of the disorder.
;

