# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_14P
_database_code_depnum_ccdc_archive 'CCDC 1588474'
_audit_update_record             
;
2017-11-30 deposited with the CCDC.
2018-01-18 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C19 H20 I N2 O2'
_chemical_formula_moiety         'C19 H20 I N2 O2'
_chemical_formula_weight         435.28
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   8.9246(13)
_cell_length_b                   26.061(4)
_cell_length_c                   15.999(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 103.344(3)
_cell_angle_gamma                90.0000
_cell_volume                     3620.6(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4235
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.40
_cell_measurement_temperature    200
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1736.00
_exptl_absorpt_coefficient_mu    1.783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.511
_exptl_absorpt_correction_T_max  0.982

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      200
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            32814
_diffrn_reflns_av_R_equivalents  0.1675
_diffrn_reflns_theta_max         27.527
_diffrn_reflns_theta_min         3.040
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             8268
_reflns_number_gt                4666
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1256
_refine_ls_R_factor_gt           0.0748
_refine_ls_wR_factor_ref         0.2065
_refine_ls_wR_factor_gt          0.1833
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         8268
_refine_ls_number_parameters     433
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1190P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         3.58
_refine_diff_density_min         -2.78
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
I I -0.4742 1.8119
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.59674(6) 0.55549(2) 0.33453(3) 0.04346(19) Uani 1 1 d . . . . .
I2 I 1.16597(7) 0.54491(2) 0.89735(4) 0.0546(2) Uani 1 1 d . . . . .
O1 O 0.0342(6) 0.26241(18) -0.1565(3) 0.0416(12) Uani 1 1 d . . . . .
O2 O 0.3118(6) 0.15885(18) 0.0601(3) 0.0430(13) Uani 1 1 d . . . . .
O3 O 0.5445(6) 0.29557(17) 0.3590(3) 0.0433(13) Uani 1 1 d . . . . .
O4 O 0.7879(6) 0.16872(17) 0.5439(3) 0.0387(12) Uani 1 1 d . . . . .
N1 N 0.0929(6) 0.2221(2) -0.1144(3) 0.0299(13) Uani 1 1 d . . . . .
N2 N 0.2270(6) 0.1733(2) -0.0123(3) 0.0276(12) Uani 1 1 d . . . . .
N3 N 0.5953(6) 0.2517(2) 0.3892(3) 0.0284(12) Uani 1 1 d . . . . .
N4 N 0.7106(6) 0.19182(19) 0.4767(3) 0.0263(12) Uani 1 1 d . . . . .
C1 C 0.1879(7) 0.2220(2) -0.0352(4) 0.0252(14) Uani 1 1 d . . . . .
C2 C 0.0700(7) 0.1701(3) -0.1543(4) 0.0308(15) Uani 1 1 d . . . . .
C3 C 0.1517(8) 0.1345(2) -0.0785(4) 0.0284(14) Uani 1 1 d . . . . .
C4 C 0.1505(10) 0.1718(3) -0.2311(4) 0.045(2) Uani 1 1 d . . . . .
H4A H 0.139382 0.138381 -0.260146 0.054 Uiso 1 1 calc R U . . .
H4B H 0.102607 0.198403 -0.271808 0.054 Uiso 1 1 calc R U . . .
H4C H 0.260108 0.179525 -0.209673 0.054 Uiso 1 1 calc R U . . .
C5 C -0.1000(8) 0.1612(3) -0.1885(5) 0.0444(19) Uani 1 1 d . . . . .
H5A H -0.116437 0.127093 -0.214835 0.053 Uiso 1 1 calc R U . . .
H5B H -0.152760 0.163357 -0.141233 0.053 Uiso 1 1 calc R U . . .
H5C H -0.141427 0.187359 -0.231638 0.053 Uiso 1 1 calc R U . . .
C6 C 0.2781(8) 0.1006(3) -0.0973(5) 0.0395(17) Uani 1 1 d . . . . .
H6A H 0.232747 0.074795 -0.140299 0.047 Uiso 1 1 calc R U . . .
H6B H 0.351472 0.121630 -0.119278 0.047 Uiso 1 1 calc R U . . .
H6C H 0.331782 0.083339 -0.044348 0.047 Uiso 1 1 calc R U . . .
C7 C 0.0427(9) 0.1037(3) -0.0383(5) 0.0450(19) Uani 1 1 d . . . . .
H7A H -0.009419 0.077786 -0.079219 0.054 Uiso 1 1 calc R U . . .
H7B H 0.100970 0.086670 0.013772 0.054 Uiso 1 1 calc R U . . .
H7C H -0.034114 0.126652 -0.023323 0.054 Uiso 1 1 calc R U . . .
C8 C 0.2421(7) 0.2681(2) 0.0149(4) 0.0243(13) Uani 1 1 d . . . . .
C9 C 0.1506(7) 0.3118(2) 0.0104(4) 0.0282(14) Uani 1 1 d . . . . .
H9 H 0.050286 0.311984 -0.026184 0.034 Uiso 1 1 calc R U . . .
C10 C 0.2036(8) 0.3548(2) 0.0582(4) 0.0293(15) Uani 1 1 d . . . . .
H10 H 0.138296 0.383908 0.054974 0.035 Uiso 1 1 calc R U . . .
C11 C 0.3523(7) 0.3565(2) 0.1115(4) 0.0248(14) Uani 1 1 d . . . . .
C12 C 0.4440(7) 0.3132(2) 0.1149(4) 0.0257(13) Uani 1 1 d . . . . .
H12 H 0.545878 0.313706 0.149666 0.031 Uiso 1 1 calc R U . . .
C13 C 0.3907(7) 0.2691(2) 0.0688(4) 0.0249(14) Uani 1 1 d . . . . .
H13 H 0.454621 0.239555 0.073758 0.030 Uiso 1 1 calc R U . . .
C14 C 0.4101(7) 0.4031(2) 0.1622(4) 0.0270(14) Uani 1 1 d . . . . .
C15 C 0.3596(10) 0.4518(3) 0.1337(6) 0.054(2) Uani 1 1 d . . . . .
H15 H 0.288362 0.455859 0.079910 0.065 Uiso 1 1 calc R U . . .
C16 C 0.4124(11) 0.4945(3) 0.1830(6) 0.059(3) Uani 1 1 d . . . . .
H16 H 0.374881 0.527515 0.163243 0.071 Uiso 1 1 calc R U . . .
C17 C 0.5192(8) 0.4900(2) 0.2608(5) 0.0356(16) Uani 1 1 d . . . . .
C18 C 0.5727(8) 0.4418(2) 0.2902(5) 0.0335(16) Uani 1 1 d . . . . .
H18 H 0.645689 0.438083 0.343471 0.040 Uiso 1 1 calc R U . . .
C19 C 0.5183(7) 0.3991(2) 0.2409(4) 0.0304(15) Uani 1 1 d . . . . .
H19 H 0.555386 0.366122 0.261062 0.036 Uiso 1 1 calc R U . . .
C20 C 0.6866(7) 0.2429(2) 0.4680(4) 0.0230(13) Uani 1 1 d . . . . .
C21 C 0.5630(7) 0.2045(2) 0.3338(4) 0.0265(14) Uani 1 1 d . . . . .
C22 C 0.6312(7) 0.1609(2) 0.3993(4) 0.0266(14) Uani 1 1 d . . . . .
C23 C 0.6508(9) 0.2123(3) 0.2626(5) 0.0399(17) Uani 1 1 d . . . . .
H23A H 0.634123 0.182550 0.224020 0.048 Uiso 1 1 calc R U . . .
H23B H 0.613144 0.243332 0.229856 0.048 Uiso 1 1 calc R U . . .
H23C H 0.761055 0.215889 0.288422 0.048 Uiso 1 1 calc R U . . .
C24 C 0.3911(8) 0.2017(3) 0.2947(5) 0.0391(18) Uani 1 1 d . . . . .
H24A H 0.368542 0.171104 0.258370 0.047 Uiso 1 1 calc R U . . .
H24B H 0.335210 0.199843 0.340605 0.047 Uiso 1 1 calc R U . . .
H24C H 0.358578 0.232400 0.259755 0.047 Uiso 1 1 calc R U . . .
C25 C 0.7517(8) 0.1285(2) 0.3728(5) 0.0342(16) Uani 1 1 d . . . . .
H25A H 0.703639 0.107898 0.322524 0.041 Uiso 1 1 calc R U . . .
H25B H 0.830742 0.150702 0.358502 0.041 Uiso 1 1 calc R U . . .
H25C H 0.799247 0.105671 0.420270 0.041 Uiso 1 1 calc R U . . .
C26 C 0.5101(8) 0.1281(3) 0.4260(5) 0.0366(17) Uani 1 1 d . . . . .
H26A H 0.433399 0.150306 0.442865 0.044 Uiso 1 1 calc R U . . .
H26B H 0.459431 0.106373 0.377773 0.044 Uiso 1 1 calc R U . . .
H26C H 0.559078 0.106439 0.474746 0.044 Uiso 1 1 calc R U . . .
C27 C 0.7536(7) 0.2826(2) 0.5289(4) 0.0218(13) Uani 1 1 d . . . . .
C28 C 0.6807(7) 0.3300(2) 0.5298(4) 0.0286(14) Uani 1 1 d . . . . .
H28 H 0.584208 0.336165 0.491231 0.034 Uiso 1 1 calc R U . . .
C29 C 0.7481(7) 0.3681(2) 0.5862(4) 0.0274(14) Uani 1 1 d . . . . .
H29 H 0.696338 0.399977 0.585618 0.033 Uiso 1 1 calc R U . . .
C30 C 0.8901(7) 0.3610(2) 0.6441(4) 0.0245(13) Uani 1 1 d . . . . .
C31 C 0.9623(7) 0.3134(2) 0.6428(4) 0.0287(14) Uani 1 1 d . . . . .
H31 H 1.060337 0.307792 0.680118 0.034 Uiso 1 1 calc R U . . .
C32 C 0.8956(7) 0.2747(2) 0.5894(4) 0.0256(14) Uani 1 1 d . . . . .
H32 H 0.944615 0.242131 0.592741 0.031 Uiso 1 1 calc R U . . .
C33 C 0.9622(7) 0.4030(2) 0.7029(4) 0.0277(14) Uani 1 1 d . . . . .
C34 C 0.9333(10) 0.4537(3) 0.6792(5) 0.047(2) Uani 1 1 d . . . . .
H34 H 0.870979 0.461631 0.624063 0.056 Uiso 1 1 calc R U . . .
C35 C 0.9948(11) 0.4935(3) 0.7354(5) 0.059(3) Uani 1 1 d . . . . .
H35 H 0.974937 0.528166 0.717872 0.071 Uiso 1 1 calc R U . . .
C36 C 1.0834(8) 0.4830(3) 0.8157(5) 0.0367(17) Uani 1 1 d . . . . .
C37 C 1.1179(8) 0.4319(3) 0.8400(4) 0.0364(16) Uani 1 1 d . . . . .
H37 H 1.182453 0.424147 0.894527 0.044 Uiso 1 1 calc R U . . .
C38 C 1.0571(7) 0.3929(3) 0.7839(4) 0.0296(14) Uani 1 1 d . . . . .
H38 H 1.080338 0.358318 0.800823 0.036 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2017/1 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# MOLECULAR GEOMETRY

_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
I1 C17 2.099(7) . ?
I2 C36 2.100(6) . ?
O1 N1 1.293(7) . ?
O2 N2 1.286(7) . ?
O3 N3 1.283(7) . ?
O4 N4 1.285(6) . ?
N1 C1 1.353(8) . ?
N1 C2 1.491(8) . ?
N2 C1 1.346(8) . ?
N2 C3 1.504(8) . ?
N3 C20 1.354(8) . ?
N3 C21 1.502(8) . ?
N4 C20 1.349(8) . ?
N4 C22 1.510(8) . ?
C1 C8 1.462(9) . ?
C2 C5 1.508(9) . ?
C2 C4 1.562(9) . ?
C2 C3 1.566(9) . ?
C3 C7 1.515(9) . ?
C3 C6 1.517(9) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.394(8) . ?
C8 C13 1.406(8) . ?
C9 C10 1.378(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.403(9) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(9) . ?
C11 C14 1.485(9) . ?
C12 C13 1.389(8) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.390(9) . ?
C14 C19 1.404(9) . ?
C15 C16 1.382(11) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(11) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(9) . ?
C18 C19 1.385(9) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C27 1.453(8) . ?
C21 C24 1.519(9) . ?
C21 C23 1.538(9) . ?
C21 C22 1.570(9) . ?
C22 C25 1.504(9) . ?
C22 C26 1.516(9) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.399(8) . ?
C27 C32 1.420(8) . ?
C28 C29 1.381(8) . ?
C28 H28 0.9500 . ?
C29 C30 1.399(8) . ?
C29 H29 0.9500 . ?
C30 C31 1.402(9) . ?
C30 C33 1.488(9) . ?
C31 C32 1.366(8) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C34 1.384(9) . ?
C33 C38 1.401(9) . ?
C34 C35 1.400(10) . ?
C34 H34 0.9500 . ?
C35 C36 1.371(10) . ?
C35 H35 0.9500 . ?
C36 C37 1.402(10) . ?
C37 C38 1.380(9) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?

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
O1 N1 C1 125.4(5) . . ?
O1 N1 C2 121.2(5) . . ?
C1 N1 C2 113.2(5) . . ?
O2 N2 C1 125.6(5) . . ?
O2 N2 C3 120.8(5) . . ?
C1 N2 C3 113.4(5) . . ?
O3 N3 C20 125.9(5) . . ?
O3 N3 C21 120.3(5) . . ?
C20 N3 C21 113.8(5) . . ?
O4 N4 C20 126.2(5) . . ?
O4 N4 C22 119.8(5) . . ?
C20 N4 C22 114.0(5) . . ?
N2 C1 N1 108.8(5) . . ?
N2 C1 C8 126.5(6) . . ?
N1 C1 C8 124.7(6) . . ?
N1 C2 C5 108.8(6) . . ?
N1 C2 C4 105.6(5) . . ?
C5 C2 C4 109.0(6) . . ?
N1 C2 C3 102.3(5) . . ?
C5 C2 C3 116.1(6) . . ?
C4 C2 C3 114.2(6) . . ?
N2 C3 C7 106.5(5) . . ?
N2 C3 C6 107.4(5) . . ?
C7 C3 C6 110.8(6) . . ?
N2 C3 C2 101.6(5) . . ?
C7 C3 C2 114.4(6) . . ?
C6 C3 C2 115.2(6) . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 118.3(6) . . ?
C9 C8 C1 121.8(6) . . ?
C13 C8 C1 119.8(6) . . ?
C10 C9 C8 121.0(6) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 121.2(6) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 117.7(6) . . ?
C12 C11 C14 121.1(6) . . ?
C10 C11 C14 121.2(6) . . ?
C11 C12 C13 121.7(6) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C12 C13 C8 120.0(6) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C15 C14 C19 117.8(6) . . ?
C15 C14 C11 121.5(6) . . ?
C19 C14 C11 120.7(6) . . ?
C16 C15 C14 120.4(7) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 121.2(7) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C18 119.5(6) . . ?
C16 C17 I1 120.4(5) . . ?
C18 C17 I1 120.1(5) . . ?
C19 C18 C17 119.1(7) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C18 C19 C14 122.0(6) . . ?
C18 C19 H19 119.0 . . ?
C14 C19 H19 119.0 . . ?
N4 C20 N3 108.1(5) . . ?
N4 C20 C27 127.0(5) . . ?
N3 C20 C27 124.8(5) . . ?
N3 C21 C24 108.7(5) . . ?
N3 C21 C23 105.6(5) . . ?
C24 C21 C23 109.8(6) . . ?
N3 C21 C22 101.9(5) . . ?
C24 C21 C22 116.1(5) . . ?
C23 C21 C22 113.8(5) . . ?
C25 C22 N4 107.5(5) . . ?
C25 C22 C26 111.4(6) . . ?
N4 C22 C26 107.4(5) . . ?
C25 C22 C21 114.3(5) . . ?
N4 C22 C21 101.4(5) . . ?
C26 C22 C21 113.9(5) . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 C26 H26A 109.5 . . ?
C22 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C22 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 C32 117.8(6) . . ?
C28 C27 C20 121.1(5) . . ?
C32 C27 C20 121.2(5) . . ?
C29 C28 C27 120.5(6) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C28 C29 C30 122.0(6) . . ?
C28 C29 H29 119.0 . . ?
C30 C29 H29 119.0 . . ?
C29 C30 C31 117.1(6) . . ?
C29 C30 C33 121.1(6) . . ?
C31 C30 C33 121.8(6) . . ?
C32 C31 C30 121.9(6) . . ?
C32 C31 H31 119.1 . . ?
C30 C31 H31 119.1 . . ?
C31 C32 C27 120.7(6) . . ?
C31 C32 H32 119.7 . . ?
C27 C32 H32 119.7 . . ?
C34 C33 C38 117.9(6) . . ?
C34 C33 C30 120.2(6) . . ?
C38 C33 C30 122.0(6) . . ?
C33 C34 C35 120.8(7) . . ?
C33 C34 H34 119.6 . . ?
C35 C34 H34 119.6 . . ?
C36 C35 C34 120.7(7) . . ?
C36 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C35 C36 C37 119.5(6) . . ?
C35 C36 I2 118.2(5) . . ?
C37 C36 I2 122.3(5) . . ?
C38 C37 C36 119.4(6) . . ?
C38 C37 H37 120.3 . . ?
C36 C37 H37 120.3 . . ?
C37 C38 C33 121.8(6) . . ?
C37 C38 H38 119.1 . . ?
C33 C38 H38 119.1 . . ?

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
O2 N2 C1 N1 -177.5(6) . . . . ?
C3 N2 C1 N1 -1.8(8) . . . . ?
O2 N2 C1 C8 4.6(11) . . . . ?
C3 N2 C1 C8 -179.7(6) . . . . ?
O1 N1 C1 N2 -179.3(6) . . . . ?
C2 N1 C1 N2 -4.2(8) . . . . ?
O1 N1 C1 C8 -1.4(10) . . . . ?
C2 N1 C1 C8 173.7(6) . . . . ?
O1 N1 C2 C5 -53.3(8) . . . . ?
C1 N1 C2 C5 131.3(6) . . . . ?
O1 N1 C2 C4 63.5(7) . . . . ?
C1 N1 C2 C4 -111.9(6) . . . . ?
O1 N1 C2 C3 -176.7(5) . . . . ?
C1 N1 C2 C3 7.9(7) . . . . ?
O2 N2 C3 C7 62.4(7) . . . . ?
C1 N2 C3 C7 -113.5(6) . . . . ?
O2 N2 C3 C6 -56.3(8) . . . . ?
C1 N2 C3 C6 127.8(6) . . . . ?
O2 N2 C3 C2 -177.6(6) . . . . ?
C1 N2 C3 C2 6.5(7) . . . . ?
N1 C2 C3 N2 -7.9(6) . . . . ?
C5 C2 C3 N2 -126.2(6) . . . . ?
C4 C2 C3 N2 105.6(6) . . . . ?
N1 C2 C3 C7 106.3(6) . . . . ?
C5 C2 C3 C7 -11.9(8) . . . . ?
C4 C2 C3 C7 -140.1(6) . . . . ?
N1 C2 C3 C6 -123.6(6) . . . . ?
C5 C2 C3 C6 118.1(7) . . . . ?
C4 C2 C3 C6 -10.1(8) . . . . ?
N2 C1 C8 C9 -148.9(7) . . . . ?
N1 C1 C8 C9 33.6(10) . . . . ?
N2 C1 C8 C13 31.6(10) . . . . ?
N1 C1 C8 C13 -145.9(6) . . . . ?
C13 C8 C9 C10 -0.6(9) . . . . ?
C1 C8 C9 C10 179.9(6) . . . . ?
C8 C9 C10 C11 1.4(10) . . . . ?
C9 C10 C11 C12 -0.4(9) . . . . ?
C9 C10 C11 C14 179.3(6) . . . . ?
C10 C11 C12 C13 -1.3(9) . . . . ?
C14 C11 C12 C13 179.0(6) . . . . ?
C11 C12 C13 C8 2.0(9) . . . . ?
C9 C8 C13 C12 -1.1(9) . . . . ?
C1 C8 C13 C12 178.5(6) . . . . ?
C12 C11 C14 C15 149.7(7) . . . . ?
C10 C11 C14 C15 -30.0(10) . . . . ?
C12 C11 C14 C19 -30.2(9) . . . . ?
C10 C11 C14 C19 150.1(6) . . . . ?
C19 C14 C15 C16 -1.6(13) . . . . ?
C11 C14 C15 C16 178.5(8) . . . . ?
C14 C15 C16 C17 1.5(15) . . . . ?
C15 C16 C17 C18 -0.8(13) . . . . ?
C15 C16 C17 I1 -179.8(7) . . . . ?
C16 C17 C18 C19 0.1(11) . . . . ?
I1 C17 C18 C19 179.2(5) . . . . ?
C17 C18 C19 C14 -0.3(11) . . . . ?
C15 C14 C19 C18 1.0(11) . . . . ?
C11 C14 C19 C18 -179.1(6) . . . . ?
O4 N4 C20 N3 -177.8(6) . . . . ?
C22 N4 C20 N3 -0.1(7) . . . . ?
O4 N4 C20 C27 5.9(10) . . . . ?
C22 N4 C20 C27 -176.4(6) . . . . ?
O3 N3 C20 N4 177.9(6) . . . . ?
C21 N3 C20 N4 -5.9(7) . . . . ?
O3 N3 C20 C27 -5.7(10) . . . . ?
C21 N3 C20 C27 170.5(6) . . . . ?
O3 N3 C21 C24 -51.5(8) . . . . ?
C20 N3 C21 C24 132.0(6) . . . . ?
O3 N3 C21 C23 66.3(7) . . . . ?
C20 N3 C21 C23 -110.2(6) . . . . ?
O3 N3 C21 C22 -174.6(5) . . . . ?
C20 N3 C21 C22 9.0(7) . . . . ?
O4 N4 C22 C25 -56.4(7) . . . . ?
C20 N4 C22 C25 125.8(6) . . . . ?
O4 N4 C22 C26 63.6(7) . . . . ?
C20 N4 C22 C26 -114.2(6) . . . . ?
O4 N4 C22 C21 -176.7(5) . . . . ?
C20 N4 C22 C21 5.5(6) . . . . ?
N3 C21 C22 C25 -123.2(6) . . . . ?
C24 C21 C22 C25 118.9(6) . . . . ?
C23 C21 C22 C25 -10.1(8) . . . . ?
N3 C21 C22 N4 -7.9(6) . . . . ?
C24 C21 C22 N4 -125.8(6) . . . . ?
C23 C21 C22 N4 105.2(6) . . . . ?
N3 C21 C22 C26 107.2(6) . . . . ?
C24 C21 C22 C26 -10.8(8) . . . . ?
C23 C21 C22 C26 -139.7(6) . . . . ?
N4 C20 C27 C28 -155.6(6) . . . . ?
N3 C20 C27 C28 28.7(9) . . . . ?
N4 C20 C27 C32 24.8(10) . . . . ?
N3 C20 C27 C32 -151.0(6) . . . . ?
C32 C27 C28 C29 1.8(9) . . . . ?
C20 C27 C28 C29 -177.9(6) . . . . ?
C27 C28 C29 C30 0.1(10) . . . . ?
C28 C29 C30 C31 -0.1(9) . . . . ?
C28 C29 C30 C33 178.6(6) . . . . ?
C29 C30 C31 C32 -1.9(10) . . . . ?
C33 C30 C31 C32 179.4(6) . . . . ?
C30 C31 C32 C27 4.0(10) . . . . ?
C28 C27 C32 C31 -3.8(9) . . . . ?
C20 C27 C32 C31 175.9(6) . . . . ?
C29 C30 C33 C34 -28.7(10) . . . . ?
C31 C30 C33 C34 149.9(7) . . . . ?
C29 C30 C33 C38 149.6(6) . . . . ?
C31 C30 C33 C38 -31.8(9) . . . . ?
C38 C33 C34 C35 -1.3(12) . . . . ?
C30 C33 C34 C35 177.1(7) . . . . ?
C33 C34 C35 C36 -0.8(14) . . . . ?
C34 C35 C36 C37 2.7(13) . . . . ?
C34 C35 C36 I2 -178.3(7) . . . . ?
C35 C36 C37 C38 -2.5(11) . . . . ?
I2 C36 C37 C38 178.6(5) . . . . ?
C36 C37 C38 C33 0.3(10) . . . . ?
C34 C33 C38 C37 1.5(10) . . . . ?
C30 C33 C38 C37 -176.8(6) . . . . ?

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

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
2-(4'-Iodo-1,1'-biphenyl-4-yl)-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl
####################################################################### 
# 
# 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_15P
_database_code_depnum_ccdc_archive 'CCDC 1588475'
_audit_update_record             
;
2017-11-30 deposited with the CCDC.
2018-01-18 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C25 H24 N3 O2 S'
_chemical_formula_moiety         'C25 H24 N3 O2 S'
_chemical_formula_weight         430.54
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.9325(9)
_cell_length_b                   9.7653(11)
_cell_length_c                   13.1883(16)
_cell_angle_alpha                81.1923(10)
_cell_angle_beta                 77.9080(10)
_cell_angle_gamma                74.017(8)
_cell_volume                     1075.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2938
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    150
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             454.00
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.539
_exptl_absorpt_correction_T_max  0.991

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      150
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            20985
_diffrn_reflns_av_R_equivalents  0.1995
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         3.111
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4927
_reflns_number_gt                3913
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1706
_refine_ls_wR_factor_gt          0.1651
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4927
_refine_ls_number_parameters     280
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1024P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.45
_refine_diff_density_min         -0.80
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.54706(5) 0.09411(5) 0.31993(3) 0.02748(17) Uani 1 1 d . . . . .
O1 O -0.23244(19) 0.46980(15) 0.43303(11) 0.0405(4) Uani 1 1 d . . . . .
O2 O 0.08797(18) 0.07058(17) 0.58968(11) 0.0419(4) Uani 1 1 d . . . . .
N1 N -0.18177(19) 0.36434(16) 0.49800(11) 0.0249(4) Uani 1 1 d . . . . .
N2 N -0.02739(19) 0.17946(17) 0.57389(11) 0.0252(4) Uani 1 1 d . . . . .
N3 N 0.42134(18) 0.22048(16) 0.11397(11) 0.0207(3) Uani 1 1 d . . . . .
C1 C -0.0397(2) 0.26842(19) 0.48488(13) 0.0236(4) Uani 1 1 d . . . . .
C2 C -0.2862(2) 0.3248(2) 0.59750(13) 0.0244(4) Uani 1 1 d . . . . .
C3 C -0.1588(2) 0.23339(19) 0.66084(13) 0.0226(4) Uani 1 1 d . . . . .
C4 C -0.3898(3) 0.4583(2) 0.64514(16) 0.0373(5) Uani 1 1 d . . . . .
H4A H -0.456928 0.430986 0.709688 0.045 Uiso 1 1 calc R U . . .
H4B H -0.322962 0.514201 0.660632 0.045 Uiso 1 1 calc R U . . .
H4C H -0.456524 0.516197 0.595910 0.045 Uiso 1 1 calc R U . . .
C5 C -0.3858(3) 0.2371(2) 0.56747(16) 0.0358(5) Uani 1 1 d . . . . .
H5A H -0.456365 0.208418 0.629760 0.043 Uiso 1 1 calc R U . . .
H5B H -0.448939 0.295357 0.516400 0.043 Uiso 1 1 calc R U . . .
H5C H -0.315752 0.151515 0.537071 0.043 Uiso 1 1 calc R U . . .
C6 C -0.0926(3) 0.3214(3) 0.71835(16) 0.0395(5) Uani 1 1 d . . . . .
H6A H -0.173230 0.360096 0.776662 0.047 Uiso 1 1 calc R U . . .
H6B H 0.000799 0.260128 0.744996 0.047 Uiso 1 1 calc R U . . .
H6C H -0.062732 0.400382 0.670312 0.047 Uiso 1 1 calc R U . . .
C7 C -0.2067(2) 0.1096(2) 0.73267(14) 0.0281(4) Uani 1 1 d . . . . .
H7A H -0.292505 0.147113 0.788794 0.034 Uiso 1 1 calc R U . . .
H7B H -0.242843 0.051772 0.692902 0.034 Uiso 1 1 calc R U . . .
H7C H -0.115611 0.050048 0.762659 0.034 Uiso 1 1 calc R U . . .
C8 C 0.3534(2) 0.18787(18) 0.30520(13) 0.0194(4) Uani 1 1 d . . . . .
C9 C 0.2398(2) 0.20124(19) 0.39520(13) 0.0219(4) Uani 1 1 d . . . . .
H9 H 0.271323 0.169334 0.461068 0.026 Uiso 1 1 calc R U . . .
C10 C 0.0797(2) 0.26086(19) 0.39060(13) 0.0221(4) Uani 1 1 d . . . . .
C11 C 0.0367(2) 0.3115(2) 0.29347(13) 0.0246(4) Uani 1 1 d . . . . .
H11 H -0.071301 0.353599 0.288769 0.029 Uiso 1 1 calc R U . . .
C12 C 0.1498(2) 0.30116(19) 0.20403(13) 0.0225(4) Uani 1 1 d . . . . .
H12 H 0.118208 0.338085 0.138719 0.027 Uiso 1 1 calc R U . . .
C13 C 0.3098(2) 0.23775(18) 0.20694(12) 0.0189(4) Uani 1 1 d . . . . .
C14 C 0.5857(2) 0.19686(17) 0.11000(13) 0.0185(4) Uani 1 1 d . . . . .
C15 C 0.6858(2) 0.21883(19) 0.01553(13) 0.0224(4) Uani 1 1 d . . . . .
H15 H 0.641879 0.253709 -0.045954 0.027 Uiso 1 1 calc R U . . .
C16 C 0.8483(2) 0.1906(2) 0.00994(14) 0.0261(4) Uani 1 1 d . . . . .
H16 H 0.914403 0.203260 -0.055496 0.031 Uiso 1 1 calc R U . . .
C17 C 0.9148(2) 0.1441(2) 0.09892(14) 0.0267(4) Uani 1 1 d . . . . .
H17 H 1.025734 0.126411 0.095298 0.032 Uiso 1 1 calc R U . . .
C18 C 0.8166(2) 0.12392(19) 0.19350(14) 0.0241(4) Uani 1 1 d . . . . .
H18 H 0.860842 0.093667 0.255207 0.029 Uiso 1 1 calc R U . . .
C19 C 0.6555(2) 0.14715(18) 0.19921(13) 0.0198(4) Uani 1 1 d . . . . .
C20 C 0.3632(2) 0.26855(19) 0.01658(12) 0.0194(4) Uani 1 1 d . . . . .
C21 C 0.3346(2) 0.41207(19) -0.02124(14) 0.0252(4) Uani 1 1 d . . . . .
H21 H 0.351339 0.479619 0.017155 0.030 Uiso 1 1 calc R U . . .
C22 C 0.2812(2) 0.4568(2) -0.11544(14) 0.0278(4) Uani 1 1 d . . . . .
H22 H 0.261409 0.555154 -0.141538 0.033 Uiso 1 1 calc R U . . .
C23 C 0.2570(2) 0.3588(2) -0.17108(14) 0.0285(4) Uani 1 1 d . . . . .
H23 H 0.221596 0.389391 -0.235880 0.034 Uiso 1 1 calc R U . . .
C24 C 0.2842(2) 0.2156(2) -0.13252(15) 0.0296(4) Uani 1 1 d . . . . .
H24 H 0.266341 0.148321 -0.170634 0.036 Uiso 1 1 calc R U . . .
C25 C 0.3377(2) 0.1700(2) -0.03820(14) 0.0246(4) Uani 1 1 d . . . . .
H25 H 0.356371 0.071840 -0.011740 0.030 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2017/1 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# MOLECULAR GEOMETRY

_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
S1 C8 1.7558(19) . ?
S1 C19 1.7661(17) . ?
O1 N1 1.2787(19) . ?
O2 N2 1.286(2) . ?
N1 C1 1.350(2) . ?
N1 C2 1.507(2) . ?
N2 C1 1.354(2) . ?
N2 C3 1.500(2) . ?
N3 C13 1.409(2) . ?
N3 C14 1.413(2) . ?
N3 C20 1.449(2) . ?
C1 C10 1.455(2) . ?
C2 C4 1.515(3) . ?
C2 C5 1.534(3) . ?
C2 C3 1.549(3) . ?
C3 C7 1.518(2) . ?
C3 C6 1.527(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.388(2) . ?
C8 C13 1.408(2) . ?
C9 C10 1.398(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(2) . ?
C11 C12 1.380(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.398(2) . ?
C12 H12 0.9500 . ?
C14 C15 1.398(2) . ?
C14 C19 1.405(2) . ?
C15 C16 1.389(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(3) . ?
C18 H18 0.9500 . ?
C20 C25 1.380(2) . ?
C20 C21 1.386(2) . ?
C21 C22 1.389(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.377(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.386(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.391(2) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

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
C8 S1 C19 101.08(8) . . ?
O1 N1 C1 126.64(15) . . ?
O1 N1 C2 121.80(15) . . ?
C1 N1 C2 111.31(14) . . ?
O2 N2 C1 126.74(16) . . ?
O2 N2 C3 121.61(14) . . ?
C1 N2 C3 111.25(15) . . ?
C13 N3 C14 123.26(14) . . ?
C13 N3 C20 117.46(14) . . ?
C14 N3 C20 116.96(14) . . ?
N1 C1 N2 108.53(15) . . ?
N1 C1 C10 125.76(16) . . ?
N2 C1 C10 125.71(17) . . ?
N1 C2 C4 110.40(15) . . ?
N1 C2 C5 106.05(15) . . ?
C4 C2 C5 111.32(18) . . ?
N1 C2 C3 100.08(14) . . ?
C4 C2 C3 114.90(16) . . ?
C5 C2 C3 113.13(15) . . ?
N2 C3 C7 110.80(15) . . ?
N2 C3 C6 105.27(15) . . ?
C7 C3 C6 111.18(15) . . ?
N2 C3 C2 100.31(13) . . ?
C7 C3 C2 114.55(15) . . ?
C6 C3 C2 113.78(16) . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 120.38(16) . . ?
C9 C8 S1 116.85(13) . . ?
C13 C8 S1 122.57(14) . . ?
C8 C9 C10 121.14(16) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 118.45(16) . . ?
C11 C10 C1 120.69(17) . . ?
C9 C10 C1 120.85(16) . . ?
C12 C11 C10 120.51(17) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 121.76(16) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C12 C13 C8 117.71(16) . . ?
C12 C13 N3 120.57(15) . . ?
C8 C13 N3 121.68(16) . . ?
C15 C14 C19 117.45(16) . . ?
C15 C14 N3 120.68(15) . . ?
C19 C14 N3 121.85(15) . . ?
C16 C15 C14 121.21(16) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 120.55(17) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 118.87(17) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C19 C18 C17 120.95(17) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C14 120.92(16) . . ?
C18 C19 S1 116.68(13) . . ?
C14 C19 S1 122.08(14) . . ?
C25 C20 C21 120.46(16) . . ?
C25 C20 N3 119.36(15) . . ?
C21 C20 N3 120.18(15) . . ?
C20 C21 C22 119.78(17) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C23 C22 C21 120.07(17) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 119.99(17) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C25 120.24(17) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C20 C25 C24 119.45(17) . . ?
C20 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?

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
O1 N1 C1 N2 176.03(18) . . . . ?
C2 N1 C1 N2 -9.6(2) . . . . ?
O1 N1 C1 C10 -4.6(3) . . . . ?
C2 N1 C1 C10 169.77(17) . . . . ?
O2 N2 C1 N1 176.74(18) . . . . ?
C3 N2 C1 N1 -10.5(2) . . . . ?
O2 N2 C1 C10 -2.7(3) . . . . ?
C3 N2 C1 C10 170.05(16) . . . . ?
O1 N1 C2 C4 -39.6(2) . . . . ?
C1 N1 C2 C4 145.76(18) . . . . ?
O1 N1 C2 C5 81.1(2) . . . . ?
C1 N1 C2 C5 -93.53(18) . . . . ?
O1 N1 C2 C3 -161.09(17) . . . . ?
C1 N1 C2 C3 24.27(19) . . . . ?
O2 N2 C3 C7 -40.6(2) . . . . ?
C1 N2 C3 C7 146.25(16) . . . . ?
O2 N2 C3 C6 79.7(2) . . . . ?
C1 N2 C3 C6 -93.47(18) . . . . ?
O2 N2 C3 C2 -161.99(17) . . . . ?
C1 N2 C3 C2 24.86(19) . . . . ?
N1 C2 C3 N2 -27.19(16) . . . . ?
C4 C2 C3 N2 -145.41(16) . . . . ?
C5 C2 C3 N2 85.23(17) . . . . ?
N1 C2 C3 C7 -145.87(15) . . . . ?
C4 C2 C3 C7 95.9(2) . . . . ?
C5 C2 C3 C7 -33.4(2) . . . . ?
N1 C2 C3 C6 84.69(17) . . . . ?
C4 C2 C3 C6 -33.5(2) . . . . ?
C5 C2 C3 C6 -162.89(17) . . . . ?
C19 S1 C8 C9 -163.81(14) . . . . ?
C19 S1 C8 C13 21.36(17) . . . . ?
C13 C8 C9 C10 1.6(3) . . . . ?
S1 C8 C9 C10 -173.34(14) . . . . ?
C8 C9 C10 C11 -2.2(3) . . . . ?
C8 C9 C10 C1 177.08(16) . . . . ?
N1 C1 C10 C11 -26.5(3) . . . . ?
N2 C1 C10 C11 152.81(19) . . . . ?
N1 C1 C10 C9 154.19(18) . . . . ?
N2 C1 C10 C9 -26.5(3) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?
C1 C10 C11 C12 -178.49(16) . . . . ?
C10 C11 C12 C13 1.2(3) . . . . ?
C11 C12 C13 C8 -1.8(3) . . . . ?
C11 C12 C13 N3 176.00(16) . . . . ?
C9 C8 C13 C12 0.4(3) . . . . ?
S1 C8 C13 C12 175.07(13) . . . . ?
C9 C8 C13 N3 -177.38(15) . . . . ?
S1 C8 C13 N3 -2.7(2) . . . . ?
C14 N3 C13 C12 161.16(16) . . . . ?
C20 N3 C13 C12 -1.0(2) . . . . ?
C14 N3 C13 C8 -21.1(3) . . . . ?
C20 N3 C13 C8 176.73(15) . . . . ?
C13 N3 C14 C15 -162.53(16) . . . . ?
C20 N3 C14 C15 -0.3(2) . . . . ?
C13 N3 C14 C19 19.2(2) . . . . ?
C20 N3 C14 C19 -178.56(16) . . . . ?
C19 C14 C15 C16 0.9(3) . . . . ?
N3 C14 C15 C16 -177.44(16) . . . . ?
C14 C15 C16 C17 -2.1(3) . . . . ?
C15 C16 C17 C18 1.1(3) . . . . ?
C16 C17 C18 C19 1.1(3) . . . . ?
C17 C18 C19 C14 -2.3(3) . . . . ?
C17 C18 C19 S1 171.40(14) . . . . ?
C15 C14 C19 C18 1.3(2) . . . . ?
N3 C14 C19 C18 179.60(16) . . . . ?
C15 C14 C19 S1 -172.08(13) . . . . ?
N3 C14 C19 S1 6.3(2) . . . . ?
C8 S1 C19 C18 163.35(14) . . . . ?
C8 S1 C19 C14 -23.04(16) . . . . ?
C13 N3 C20 C25 -99.0(2) . . . . ?
C14 N3 C20 C25 97.71(19) . . . . ?
C13 N3 C20 C21 81.4(2) . . . . ?
C14 N3 C20 C21 -81.9(2) . . . . ?
C25 C20 C21 C22 -0.6(3) . . . . ?
N3 C20 C21 C22 179.00(16) . . . . ?
C20 C21 C22 C23 0.0(3) . . . . ?
C21 C22 C23 C24 0.7(3) . . . . ?
C22 C23 C24 C25 -0.7(3) . . . . ?
C21 C20 C25 C24 0.6(3) . . . . ?
N3 C20 C25 C24 -179.00(17) . . . . ?
C23 C24 C25 C20 0.0(3) . . . . ?

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

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
2-(10-Phenyl-10H-phenothiazine-3-yl)-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl
