# Electronic Supplementary Material (ESI) for RSC Advances.
# 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. 
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data_M1K4
_database_code_depnum_ccdc_archive 'CCDC 1434497'
_audit_update_record             
;
2016-02-02 deposited with the CCDC.
2016-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'Mercury thiocyanate complex(zohori-(tez-Masoudi)'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H23 Hg N7 O4 S2'
_chemical_formula_weight         738.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   8.4523(8)
_cell_length_b                   11.6846(12)
_cell_length_c                   27.114(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.952(4)
_cell_angle_gamma                90
_cell_volume                     2676.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9879
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      26.03

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.076
_exptl_absorpt_coefficient_mu    5.952
_shelx_estimated_absorpt_T_min   0.307
_shelx_estimated_absorpt_T_max   0.660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5799
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'SADBAS, Bruker-AXS, 2008'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29879
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.743
_diffrn_reflns_theta_max         26.181
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.00
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.00
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.00
_reflns_number_total             5364
_reflns_number_gt                4814
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0900P)²+105.1749P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5364
_refine_ls_number_parameters     351
_refine_ls_number_restraints     327
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0822
_refine_ls_wR_factor_ref         0.2204
_refine_ls_wR_factor_gt          0.2136
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_restrained_S_all      1.133
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.001

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
Hg1 Hg 0.79376(8) 0.19317(6) 0.28544(2) 0.0241(2) Uani 1 1 d . U . . .
S1 S 0.6665(6) 0.3685(4) 0.33021(18) 0.0321(10) Uani 1 1 d . U . . .
C1S C 0.569(2) 0.4279(15) 0.2822(7) 0.029(3) Uani 1 1 d . U . . .
N1S N 0.491(2) 0.4683(17) 0.2513(7) 0.043(4) Uani 1 1 d . U . . .
S2 S 0.8623(6) 0.0587(4) 0.35361(18) 0.0298(10) Uani 1 1 d . U . . .
C2S C 0.820(2) 0.1511(17) 0.3983(7) 0.031(4) Uani 1 1 d . U . . .
N2S N 0.791(3) 0.2158(16) 0.4286(7) 0.048(5) Uani 1 1 d . U . . .
O1 O 0.173(2) -0.1617(12) 0.3649(6) 0.042(3) Uani 1 1 d . U . . .
O2 O 0.023(2) -0.1740(18) 0.4273(6) 0.060(5) Uani 1 1 d . U . . .
N1 N 0.1326(19) -0.1304(14) 0.4054(6) 0.032(3) Uani 1 1 d . U . . .
C1 C 0.213(2) -0.0293(17) 0.4297(8) 0.032(3) Uani 1 1 d . U . . .
C2 C 0.206(2) -0.0280(18) 0.4794(8) 0.036(4) Uani 1 1 d . U . . .
H2 H 0.1460 -0.0836 0.4963 0.043 Uiso 1 1 calc R U . . .
C3 C 0.288(3) 0.0565(18) 0.5049(8) 0.040(4) Uani 1 1 d . U . . .
H3 H 0.2835 0.0622 0.5398 0.048 Uiso 1 1 calc R U . . .
C4 C 0.379(3) 0.1336(19) 0.4782(8) 0.037(4) Uani 1 1 d . U . . .
H4 H 0.4412 0.1892 0.4955 0.044 Uiso 1 1 calc R U . . .
C5 C 0.380(2) 0.1308(17) 0.4289(8) 0.033(4) Uani 1 1 d . U . . .
H5 H 0.4388 0.1871 0.4121 0.039 Uiso 1 1 calc R U . . .
C6 C 0.296(2) 0.0461(14) 0.4006(7) 0.024(3) Uani 1 1 d . U . . .
C7 C 0.296(2) 0.0490(14) 0.3476(7) 0.024(3) Uani 1 1 d . U . . .
H7 H 0.2044 0.0225 0.3298 0.029 Uiso 1 1 calc R U . . .
C8 C 0.419(2) 0.0874(16) 0.3219(7) 0.025(3) Uani 1 1 d . U . . .
H8 H 0.5120 0.1107 0.3399 0.030 Uiso 1 1 calc R U . . .
C9 C 0.418(2) 0.0951(15) 0.2688(7) 0.024(3) Uani 1 1 d . U . . .
H9 H 0.3253 0.0770 0.2498 0.029 Uiso 1 1 calc R U . . .
N2 N 0.5426(17) 0.1262(12) 0.2475(5) 0.021(3) Uani 1 1 d . U . . .
C10 C 0.546(2) 0.1283(17) 0.1926(7) 0.028(4) Uani 1 1 d . U . . .
H10A H 0.4380 0.1412 0.1784 0.034 Uiso 1 1 calc R U . . .
H10B H 0.5849 0.0541 0.1802 0.034 Uiso 1 1 calc R U . . .
C11 C 0.656(2) 0.2247(16) 0.1769(7) 0.028(3) Uani 1 1 d . U . . .
H11A H 0.6620 0.2255 0.1405 0.034 Uiso 1 1 calc R U . . .
H11B H 0.6130 0.2993 0.1875 0.034 Uiso 1 1 calc R U . . .
N3 N 0.8144(16) 0.2067(12) 0.1997(5) 0.024(3) Uani 1 1 d . U . . .
H3A H 0.8564 0.1324 0.1874 0.029 Uiso 1 1 calc R U . . .
C12 C 0.929(2) 0.2966(17) 0.1890(7) 0.031(3) Uani 1 1 d . U . . .
H12A H 0.8844 0.3723 0.1974 0.037 Uiso 1 1 calc R U . . .
H12B H 0.9508 0.2962 0.1534 0.037 Uiso 1 1 calc R U . . .
C13 C 1.082(2) 0.2754(15) 0.2194(7) 0.028(3) Uani 1 1 d . U . . .
H13A H 1.1243 0.1982 0.2125 0.033 Uiso 1 1 calc R U . . .
H13B H 1.1633 0.3327 0.2110 0.033 Uiso 1 1 calc R U . . .
N4 N 1.0455(17) 0.2848(11) 0.2697(6) 0.023(3) Uani 1 1 d . U . . .
C14 C 1.153(2) 0.3290(13) 0.3007(7) 0.025(3) Uani 1 1 d . U . . .
H14 H 1.2529 0.3480 0.2881 0.030 Uiso 1 1 calc R U . . .
C15 C 1.128(2) 0.3500(16) 0.3516(7) 0.029(3) Uani 1 1 d . U . . .
H15 H 1.0337 0.3261 0.3665 0.034 Uiso 1 1 calc R U . . .
C16 C 1.242(2) 0.4042(15) 0.3779(7) 0.030(3) Uani 1 1 d . U . . .
H16 H 1.3365 0.4214 0.3615 0.037 Uiso 1 1 calc R U . . .
C17 C 1.235(2) 0.4398(15) 0.4300(7) 0.030(3) Uani 1 1 d . U . . .
C18 C 1.310(3) 0.5356(17) 0.4505(8) 0.036(4) Uani 1 1 d . U . . .
C19 C 1.303(3) 0.565(2) 0.4991(8) 0.046(5) Uani 1 1 d . U . . .
H19 H 1.3528 0.6332 0.5110 0.055 Uiso 1 1 calc R U . . .
C20 C 1.223(3) 0.494(2) 0.5311(9) 0.044(5) Uani 1 1 d . U . . .
H20 H 1.2184 0.5125 0.5651 0.053 Uiso 1 1 calc R U . . .
C21 C 1.149(3) 0.3950(19) 0.5131(8) 0.039(4) Uani 1 1 d . U . . .
H21 H 1.0970 0.3450 0.5350 0.047 Uiso 1 1 calc R U . . .
C22 C 1.151(2) 0.3703(17) 0.4636(8) 0.034(4) Uani 1 1 d . U . . .
H22 H 1.0958 0.3049 0.4514 0.041 Uiso 1 1 calc R U . . .
N5 N 1.397(3) 0.6160(17) 0.4187(8) 0.046(4) Uani 1 1 d . U . . .
O3A O 1.413(5) 0.722(3) 0.4358(14) 0.051(5) Uani 0.5 1 d . U P A 1
O4A O 1.360(5) 0.605(3) 0.3733(13) 0.050(5) Uani 0.5 1 d . U P A 1
O3B O 1.483(5) 0.681(3) 0.4348(14) 0.051(5) Uani 0.5 1 d . U P A 2
O4B O 1.464(5) 0.589(3) 0.3813(13) 0.050(5) Uani 0.5 1 d . U P A 2


_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
Hg1 N3 2.343(14) . ?
Hg1 N4 2.433(14) . ?
Hg1 N2 2.455(14) . ?
Hg1 S2 2.480(5) . ?
Hg1 S1 2.630(5) . ?
S1 C1S 1.67(2) . ?
C1S N1S 1.15(3) . ?
S2 C2S 1.67(2) . ?
C2S N2S 1.15(3) . ?
O1 N1 1.22(2) . ?
O2 N1 1.23(2) . ?
N1 C1 1.50(3) . ?
C1 C2 1.35(3) . ?
C1 C6 1.39(3) . ?
C2 C3 1.38(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.40(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.34(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.43(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.44(3) . ?
C7 C8 1.35(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.44(3) . ?
C8 H8 0.9500 . ?
C9 N2 1.27(2) . ?
C9 H9 0.9500 . ?
N2 C10 1.49(2) . ?
C10 C11 1.53(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N3 1.47(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N3 C12 1.46(2) . ?
N3 H3A 1.0000 . ?
C12 C13 1.54(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N4 1.41(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
N4 C14 1.32(2) . ?
C14 C15 1.43(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.34(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.48(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.39(3) . ?
C17 C22 1.43(3) . ?
C18 C19 1.36(3) . ?
C18 N5 1.49(3) . ?
C19 C20 1.40(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.39(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.37(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
N5 O3B 1.13(4) . ?
N5 O4B 1.22(4) . ?
N5 O4A 1.27(4) . ?
N5 O3A 1.33(4) . ?
O3B O4B 1.80(5) . ?

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
N3 Hg1 N4 72.6(5) . . ?
N3 Hg1 N2 72.4(5) . . ?
N4 Hg1 N2 144.6(5) . . ?
N3 Hg1 S2 139.4(4) . . ?
N4 Hg1 S2 103.1(4) . . ?
N2 Hg1 S2 106.7(4) . . ?
N3 Hg1 S1 116.8(4) . . ?
N4 Hg1 S1 96.4(4) . . ?
N2 Hg1 S1 94.6(3) . . ?
S2 Hg1 S1 103.80(16) . . ?
C1S S1 Hg1 99.4(7) . . ?
N1S C1S S1 174.4(19) . . ?
C2S S2 Hg1 94.7(7) . . ?
N2S C2S S2 179(2) . . ?
O1 N1 O2 123.5(18) . . ?
O1 N1 C1 119.5(16) . . ?
O2 N1 C1 116.9(17) . . ?
C2 C1 C6 126.9(19) . . ?
C2 C1 N1 114.3(17) . . ?
C6 C1 N1 118.6(17) . . ?
C1 C2 C3 118(2) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C2 C3 C4 118(2) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C5 C4 C3 122(2) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 122(2) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C1 C6 C7 127.0(17) . . ?
C1 C6 C5 112.7(17) . . ?
C7 C6 C5 120.2(17) . . ?
C8 C7 C6 123.5(17) . . ?
C8 C7 H7 118.3 . . ?
C6 C7 H7 118.3 . . ?
C7 C8 C9 124.0(17) . . ?
C7 C8 H8 118.0 . . ?
C9 C8 H8 118.0 . . ?
N2 C9 C8 119.8(17) . . ?
N2 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 N2 C10 120.2(16) . . ?
C9 N2 Hg1 128.2(13) . . ?
C10 N2 Hg1 111.5(11) . . ?
N2 C10 C11 108.8(15) . . ?
N2 C10 H10A 109.9 . . ?
C11 C10 H10A 109.9 . . ?
N2 C10 H10B 109.9 . . ?
C11 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
N3 C11 C10 109.3(15) . . ?
N3 C11 H11A 109.8 . . ?
C10 C11 H11A 109.8 . . ?
N3 C11 H11B 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
C12 N3 C11 114.4(14) . . ?
C12 N3 Hg1 108.5(11) . . ?
C11 N3 Hg1 109.2(10) . . ?
C12 N3 H3A 108.2 . . ?
C11 N3 H3A 108.2 . . ?
Hg1 N3 H3A 108.2 . . ?
N3 C12 C13 109.3(15) . . ?
N3 C12 H12A 109.8 . . ?
C13 C12 H12A 109.8 . . ?
N3 C12 H12B 109.8 . . ?
C13 C12 H12B 109.8 . . ?
H12A C12 H12B 108.3 . . ?
N4 C13 C12 107.2(15) . . ?
N4 C13 H13A 110.3 . . ?
C12 C13 H13A 110.3 . . ?
N4 C13 H13B 110.3 . . ?
C12 C13 H13B 110.3 . . ?
H13A C13 H13B 108.5 . . ?
C14 N4 C13 118.4(15) . . ?
C14 N4 Hg1 130.2(12) . . ?
C13 N4 Hg1 111.0(11) . . ?
N4 C14 C15 124.5(17) . . ?
N4 C14 H14 117.7 . . ?
C15 C14 H14 117.7 . . ?
C16 C15 C14 118.3(18) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
C15 C16 C17 126.3(19) . . ?
C15 C16 H16 116.8 . . ?
C17 C16 H16 116.8 . . ?
C18 C17 C22 115.6(18) . . ?
C18 C17 C16 125.2(18) . . ?
C22 C17 C16 119.2(17) . . ?
C19 C18 C17 124(2) . . ?
C19 C18 N5 115.9(19) . . ?
C17 C18 N5 120.3(18) . . ?
C18 C19 C20 119(2) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C21 C20 C19 120(2) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C22 C21 C20 120(2) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C17 121.9(19) . . ?
C21 C22 H22 119.0 . . ?
C17 C22 H22 119.0 . . ?
O3B N5 O4B 100(3) . . ?
O4A N5 O3A 117(3) . . ?
O3B N5 C18 122(3) . . ?
O4B N5 C18 125(2) . . ?
O4A N5 C18 113(2) . . ?
O3A N5 C18 116(2) . . ?
N5 O3B O4B 42(2) . . ?
N5 O4B O3B 37.9(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 N2S 0.95 2.60 3.32(3) 133.3 3_656
C11 H11A O2 0.99 2.65 3.37(3) 130.3 2
N3 H3A O4B 1.00 2.49 3.24(4) 131.1 2_745
C13 H13A O4A 0.99 2.58 3.26(4) 125.9 2_745
C13 H13B O1 0.99 2.52 3.22(2) 127.5 2_655
C14 H14 N1S 0.95 2.68 3.59(3) 161.5 1_655

_refine_diff_density_max         4.827
_refine_diff_density_min         -4.178
_refine_diff_density_rms         0.271

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_m2k1
_database_code_depnum_ccdc_archive 'CCDC 1434498'
_audit_update_record             
;
2016-02-02 deposited with the CCDC.
2016-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        'Mercury Iodide complex(zohori-Tez-Masoudi)'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H23 Hg I2 N5 O4'
_chemical_formula_weight         875.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   7.1329(3)
_cell_length_b                   7.3046(3)
_cell_length_c                   14.7198(7)
_cell_angle_alpha                97.922(2)
_cell_angle_beta                 97.425(2)
_cell_angle_gamma                117.0955(18)
_cell_volume                     660.03(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5830
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      27.25

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.203
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.096
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.034
_exptl_absorpt_coefficient_mu    8.205
_shelx_estimated_absorpt_T_min   0.506
_shelx_estimated_absorpt_T_max   0.768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5998
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker, 2010'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7494
_diffrn_reflns_av_unetI/netI     0.0717
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.863
_diffrn_reflns_theta_max         27.632
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.944
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.657
_diffrn_reflns_point_group_measured_fraction_full 0.706
_reflns_number_total             4034
_reflns_number_gt                3730
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.394
_reflns_Friedel_fraction_max     0.371
_reflns_Friedel_fraction_full    0.468

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2 Suite'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  
;SHELXL-2013 (Sheldrick, 2013), 
C. B. Hübschle, G. M. Sheldrick and B. Dittrich
ShelXle: a Qt graphical user interface for SHELXL
J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    'Diamond3.2 (Crystal Impact, 2009)'
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0200P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 995 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.106(6)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4034
_refine_ls_number_parameters     302
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0778
_refine_ls_wR_factor_gt          0.0767
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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_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
Hg Hg 0.66252(3) 0.68120(3) 0.50430(2) 0.03037(14) Uani 1 1 d . . . . .
I1 I 1.04717(14) 0.69051(13) 0.50433(6) 0.0371(2) Uani 1 1 d . . . . .
I2 I 0.32874(14) 0.30751(12) 0.50429(6) 0.0335(2) Uani 1 1 d . . . . .
O1 O 0.664(3) 0.061(2) -0.0765(7) 0.075(4) Uani 1 1 d . . . . .
O2 O 0.467(2) 0.0994(19) 0.0144(8) 0.060(3) Uani 1 1 d . . . . .
N1 N 0.628(3) 0.095(2) 0.0005(8) 0.050(4) Uani 1 1 d . . . . .
C1 C 0.792(3) 0.128(2) 0.0825(9) 0.044(4) Uani 1 1 d . . . . .
C2 C 0.893(3) 0.007(3) 0.0744(11) 0.053(4) Uani 1 1 d . . . . .
H2 H 0.8615 -0.0873 0.0164 0.064 Uiso 1 1 calc R U . . .
C3 C 1.034(3) 0.021(3) 0.1478(11) 0.057(5) Uani 1 1 d . . . . .
H3 H 1.1041 -0.0629 0.1428 0.069 Uiso 1 1 calc R U . . .
C4 C 1.076(3) 0.161(3) 0.2317(11) 0.055(4) Uani 1 1 d . . . . .
H4 H 1.1754 0.1725 0.2847 0.066 Uiso 1 1 calc R U . . .
C5 C 0.976(3) 0.282(3) 0.2387(10) 0.046(4) Uani 1 1 d . . . . .
H5 H 1.0096 0.3765 0.2968 0.055 Uiso 1 1 calc R U . . .
C6 C 0.829(3) 0.272(2) 0.1648(9) 0.038(3) Uani 1 1 d . . . . .
C7 C 0.732(3) 0.411(2) 0.1720(10) 0.041(4) Uani 1 1 d . . . . .
H7 H 0.6949 0.4511 0.1166 0.049 Uiso 1 1 calc R U . . .
C8 C 0.692(3) 0.484(2) 0.2520(9) 0.040(4) Uani 1 1 d . . . . .
H8 H 0.7117 0.4337 0.3066 0.048 Uiso 1 1 calc R U . . .
C9 C 0.620(3) 0.640(2) 0.2555(9) 0.037(3) Uani 1 1 d . . . . .
H9 H 0.5987 0.6877 0.2002 0.045 Uiso 1 1 calc R U . . .
N2 N 0.583(2) 0.7147(16) 0.3304(7) 0.035(3) Uani 1 1 d . . . . .
C10 C 0.530(2) 0.880(2) 0.3325(9) 0.034(3) Uani 1 1 d . . . . .
H10A H 0.3757 0.8258 0.3346 0.041 Uiso 1 1 calc R U . . .
H10B H 0.5527 0.9357 0.2748 0.041 Uiso 1 1 calc R U . . .
C11 C 0.668(2) 1.0541(19) 0.4174(9) 0.034(3) Uani 1 1 d . . . . .
H11A H 0.8220 1.1011 0.4167 0.041 Uiso 1 1 calc R U . . .
H11B H 0.6427 1.1757 0.4144 0.041 Uiso 1 1 calc R U . . .
N3 N 0.6255(16) 0.9895(13) 0.5037(6) 0.0148(16) Uiso 1 1 d . . . . .
H3A H 0.4718 0.9500 0.5043 0.018 Uiso 1 1 calc R U . . .
C12 C 0.763(2) 1.151(2) 0.5924(9) 0.036(3) Uani 1 1 d . . . . .
H12A H 0.7425 1.2761 0.5953 0.043 Uiso 1 1 calc R U . . .
H12B H 0.9174 1.1954 0.5937 0.043 Uiso 1 1 calc R U . . .
C13 C 0.700(2) 1.054(2) 0.6755(8) 0.032(3) Uani 1 1 d . . . . .
H13A H 0.7736 1.1634 0.7345 0.039 Uiso 1 1 calc R U . . .
H13B H 0.5419 0.9935 0.6700 0.039 Uiso 1 1 calc R U . . .
N4 N 0.7595(19) 0.8882(16) 0.6778(7) 0.033(2) Uani 1 1 d . . . . .
C14 C 0.867(3) 0.886(2) 0.7525(9) 0.038(3) Uani 1 1 d . . . . .
H14 H 0.8976 0.9871 0.8079 0.045 Uiso 1 1 calc R U . . .
C15 C 0.947(3) 0.737(2) 0.7577(10) 0.041(4) Uani 1 1 d . . . . .
H15 H 0.9127 0.6325 0.7029 0.049 Uiso 1 1 calc R U . . .
C16 C 1.066(3) 0.740(2) 0.8365(10) 0.045(4) Uani 1 1 d . . . . .
H16 H 1.0849 0.8340 0.8925 0.054 Uiso 1 1 calc R U . . .
C17 C 1.168(3) 0.610(2) 0.8423(9) 0.039(3) Uani 1 1 d . . . . .
C18 C 1.244(3) 0.548(3) 0.7703(11) 0.049(4) Uani 1 1 d . . . . .
H18 H 1.2216 0.5862 0.7123 0.059 Uiso 1 1 calc R U . . .
C19 C 1.351(3) 0.435(3) 0.7772(12) 0.059(5) Uani 1 1 d . . . . .
H19 H 1.3986 0.3941 0.7243 0.070 Uiso 1 1 calc R U . . .
C20 C 1.392(3) 0.378(3) 0.8606(13) 0.061(5) Uani 1 1 d . . . . .
H20 H 1.4680 0.3008 0.8657 0.073 Uiso 1 1 calc R U . . .
C21 C 1.321(3) 0.435(3) 0.9345(10) 0.052(4) Uani 1 1 d . . . . .
H21 H 1.3472 0.3981 0.9924 0.062 Uiso 1 1 calc R U . . .
C22 C 1.210(3) 0.549(2) 0.9255(10) 0.044(4) Uani 1 1 d . . . . .
N5 N 1.131(3) 0.598(2) 1.0089(8) 0.052(4) Uani 1 1 d . . . . .
O3 O 1.244(3) 0.642(2) 1.0859(7) 0.074(4) Uani 1 1 d . . . . .
O4 O 0.952(3) 0.591(2) 0.9948(8) 0.069(4) Uani 1 1 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
Hg N3 2.385(9) . ?
Hg N4 2.610(10) . ?
Hg N2 2.618(10) . ?
Hg I2 2.6831(9) . ?
Hg I1 2.7133(9) . ?
O1 N1 1.214(16) . ?
O2 N1 1.201(19) . ?
N1 C1 1.48(2) . ?
C1 C2 1.37(2) . ?
C1 C6 1.399(18) . ?
C2 C3 1.34(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.39(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.37(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.38(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.46(2) . ?
C7 C8 1.35(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.44(2) . ?
C8 H8 0.9500 . ?
C9 N2 1.273(17) . ?
C9 H9 0.9500 . ?
N2 C10 1.424(16) . ?
C10 C11 1.500(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N3 1.437(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N3 C12 1.498(16) . ?
N3 H3A 1.0000 . ?
C12 C13 1.515(18) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N4 1.456(15) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
N4 C14 1.265(17) . ?
C14 C15 1.44(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.34(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.44(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.37(2) . ?
C17 C22 1.405(19) . ?
C18 C19 1.36(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.39(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.35(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.39(2) . ?
C21 H21 0.9500 . ?
C22 N5 1.48(2) . ?
N5 O3 1.208(16) . ?
N5 O4 1.25(2) . ?

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
N3 Hg N4 71.5(3) . . ?
N3 Hg N2 70.9(3) . . ?
N4 Hg N2 142.0(3) . . ?
N3 Hg I2 122.2(2) . . ?
N4 Hg I2 102.6(2) . . ?
N2 Hg I2 102.4(3) . . ?
N3 Hg I1 121.4(2) . . ?
N4 Hg I1 96.8(3) . . ?
N2 Hg I1 97.2(3) . . ?
I2 Hg I1 116.36(3) . . ?
O2 N1 O1 124.9(14) . . ?
O2 N1 C1 118.3(12) . . ?
O1 N1 C1 116.7(15) . . ?
C2 C1 C6 123.7(15) . . ?
C2 C1 N1 117.3(12) . . ?
C6 C1 N1 118.8(13) . . ?
C3 C2 C1 120.4(15) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 118.2(16) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C5 C4 C3 120.9(15) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 122.8(14) . . ?
C4 C5 H5 118.6 . . ?
C6 C5 H5 118.6 . . ?
C5 C6 C1 113.9(14) . . ?
C5 C6 C7 122.1(12) . . ?
C1 C6 C7 123.8(14) . . ?
C8 C7 C6 124.1(13) . . ?
C8 C7 H7 118.0 . . ?
C6 C7 H7 118.0 . . ?
C7 C8 C9 120.5(12) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
N2 C9 C8 122.0(12) . . ?
N2 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C9 N2 C10 119.9(11) . . ?
C9 N2 Hg 131.8(9) . . ?
C10 N2 Hg 107.0(7) . . ?
N2 C10 C11 109.6(11) . . ?
N2 C10 H10A 109.8 . . ?
C11 C10 H10A 109.8 . . ?
N2 C10 H10B 109.8 . . ?
C11 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
N3 C11 C10 112.4(11) . . ?
N3 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
N3 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C11 N3 C12 116.1(10) . . ?
C11 N3 Hg 108.5(7) . . ?
C12 N3 Hg 108.8(7) . . ?
C11 N3 H3A 107.7 . . ?
C12 N3 H3A 107.7 . . ?
Hg N3 H3A 107.7 . . ?
N3 C12 C13 108.7(10) . . ?
N3 C12 H12A 109.9 . . ?
C13 C12 H12A 109.9 . . ?
N3 C12 H12B 109.9 . . ?
C13 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
N4 C13 C12 109.3(10) . . ?
N4 C13 H13A 109.8 . . ?
C12 C13 H13A 109.8 . . ?
N4 C13 H13B 109.8 . . ?
C12 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?
C14 N4 C13 120.4(11) . . ?
C14 N4 Hg 132.1(10) . . ?
C13 N4 Hg 106.6(7) . . ?
N4 C14 C15 123.3(13) . . ?
N4 C14 H14 118.4 . . ?
C15 C14 H14 118.4 . . ?
C16 C15 C14 122.8(13) . . ?
C16 C15 H15 118.6 . . ?
C14 C15 H15 118.6 . . ?
C15 C16 C17 124.6(14) . . ?
C15 C16 H16 117.7 . . ?
C17 C16 H16 117.7 . . ?
C18 C17 C22 114.3(14) . . ?
C18 C17 C16 123.4(13) . . ?
C22 C17 C16 122.2(14) . . ?
C19 C18 C17 123.6(15) . . ?
C19 C18 H18 118.2 . . ?
C17 C18 H18 118.2 . . ?
C18 C19 C20 120.5(17) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C21 C20 C19 118.8(17) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C20 C21 C22 119.6(14) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C21 C22 C17 123.2(14) . . ?
C21 C22 N5 116.1(12) . . ?
C17 C22 N5 120.7(14) . . ?
O3 N5 O4 124.0(14) . . ?
O3 N5 C22 118.5(15) . . ?
O4 N5 C22 117.4(12) . . ?

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 N1 C1 C2 140.6(16) . . . . ?
O1 N1 C1 C2 -38(2) . . . . ?
O2 N1 C1 C6 -36(2) . . . . ?
O1 N1 C1 C6 145.3(15) . . . . ?
C6 C1 C2 C3 0(3) . . . . ?
N1 C1 C2 C3 -176.1(17) . . . . ?
C1 C2 C3 C4 0(3) . . . . ?
C2 C3 C4 C5 0(3) . . . . ?
C3 C4 C5 C6 1(3) . . . . ?
C4 C5 C6 C1 0(3) . . . . ?
C4 C5 C6 C7 -176.6(17) . . . . ?
C2 C1 C6 C5 0(2) . . . . ?
N1 C1 C6 C5 176.3(15) . . . . ?
C2 C1 C6 C7 176.1(17) . . . . ?
N1 C1 C6 C7 -7(2) . . . . ?
C5 C6 C7 C8 -32(3) . . . . ?
C1 C6 C7 C8 152.5(17) . . . . ?
C6 C7 C8 C9 172.7(15) . . . . ?
C7 C8 C9 N2 -179.1(16) . . . . ?
C8 C9 N2 C10 174.8(14) . . . . ?
C8 C9 N2 Hg 10(2) . . . . ?
C9 N2 C10 C11 -130.6(14) . . . . ?
Hg N2 C10 C11 37.9(13) . . . . ?
N2 C10 C11 N3 -65.6(15) . . . . ?
C10 C11 N3 C12 177.5(11) . . . . ?
C10 C11 N3 Hg 54.6(12) . . . . ?
C11 N3 C12 C13 -178.6(10) . . . . ?
Hg N3 C12 C13 -55.9(11) . . . . ?
N3 C12 C13 N4 67.6(14) . . . . ?
C12 C13 N4 C14 129.2(14) . . . . ?
C12 C13 N4 Hg -41.3(12) . . . . ?
C13 N4 C14 C15 -174.9(14) . . . . ?
Hg N4 C14 C15 -7(2) . . . . ?
N4 C14 C15 C16 178.0(17) . . . . ?
C14 C15 C16 C17 -172.9(16) . . . . ?
C15 C16 C17 C18 32(3) . . . . ?
C15 C16 C17 C22 -152.3(17) . . . . ?
C22 C17 C18 C19 1(3) . . . . ?
C16 C17 C18 C19 176.3(18) . . . . ?
C17 C18 C19 C20 -1(3) . . . . ?
C18 C19 C20 C21 1(3) . . . . ?
C19 C20 C21 C22 0(3) . . . . ?
C20 C21 C22 C17 0(3) . . . . ?
C20 C21 C22 N5 177.8(18) . . . . ?
C18 C17 C22 C21 0(2) . . . . ?
C16 C17 C22 C21 -175.6(17) . . . . ?
C18 C17 C22 N5 -177.9(16) . . . . ?
C16 C17 C22 N5 6(2) . . . . ?
C21 C22 N5 O3 38(2) . . . . ?
C17 C22 N5 O3 -144.0(16) . . . . ?
C21 C22 N5 O4 -142.2(16) . . . . ?
C17 C22 N5 O4 36(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 I1 0.95 3.21 3.877(15) 128.6 .
C11 H11B I2 0.99 3.17 3.893(13) 130.8 1_565
C12 H12A I2 0.99 3.20 3.900(14) 129.1 1_565
C12 H12B I2 0.99 3.18 4.100(14) 155.1 1_665
C15 H15 I1 0.95 3.21 3.886(14) 129.2 .
C11 H11B I2 0.99 3.17 3.893(13) 130.8 1_565
C12 H12A I2 0.99 3.20 3.900(14) 129.1 1_565
C12 H12B I2 0.99 3.18 4.100(14) 155.1 1_665
C15 H15 I1 0.95 3.21 3.886(14) 129.2 .
N3 H3A I1 1.00 2.75 3.687(10) 157.1 1_455
N3 H3A I2 1.00 3.21 3.789(9) 118.5 1_565

_refine_diff_density_max         1.744
_refine_diff_density_min         -1.024
_refine_diff_density_rms         0.158

_shelxl_version_number           2013-2

