# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2089058'
loop_
_audit_author_name
_audit_author_address
'Ramesh Rasappan'
;Indian Institute of Science Education and Research
India
;
_audit_update_record             
;
2021-06-09 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H27 I N2 Si Zn'
_chemical_formula_sum            'C14 H27 I N2 Si Zn'
_chemical_formula_weight         443.73

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'
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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.0253(19)
_cell_length_b                   15.7490(19)
_cell_length_c                   16.4568(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3894.2(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    6521
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      23.65

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.513
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_F_000             1776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.085
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.045
_exptl_absorpt_coefficient_mu    2.900
_shelx_estimated_absorpt_T_min   0.791
_shelx_estimated_absorpt_T_max   0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            63027
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.1161
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.245
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3425
_reflns_number_gt                2334
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP3- 2014.1(Farrugia, 1997) '
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0390P)²+8.7419P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3425
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
C1 C 0.3581(6) 0.4965(4) 0.4846(5) 0.073(2) Uani 1 1 d . . . . .
H1A H 0.303552 0.523008 0.464105 0.110 Uiso 1 1 calc R U . . .
H1B H 0.402361 0.493848 0.440885 0.110 Uiso 1 1 calc R U . . .
H1C H 0.381811 0.530298 0.529698 0.110 Uiso 1 1 calc R U . . .
C2 C 0.4218(7) 0.3768(6) 0.5495(5) 0.102(3) Uani 1 1 d . . . . .
H2A H 0.440051 0.413512 0.594620 0.152 Uiso 1 1 calc R U . . .
H2B H 0.468654 0.375904 0.508138 0.152 Uiso 1 1 calc R U . . .
H2C H 0.411683 0.319083 0.569733 0.152 Uiso 1 1 calc R U . . .
C3 C 0.2705(7) 0.4092(7) 0.5746(5) 0.105(4) Uani 1 1 d . . . . .
H3A H 0.277763 0.357236 0.607844 0.126 Uiso 1 1 calc R U . . .
H3B H 0.279573 0.458611 0.610893 0.126 Uiso 1 1 calc R U . . .
C4 C 0.1823(7) 0.4116(7) 0.5444(6) 0.107(4) Uani 1 1 d . . . . .
H4A H 0.171090 0.468890 0.521764 0.129 Uiso 1 1 calc R U . . .
H4B H 0.140831 0.403313 0.590396 0.129 Uiso 1 1 calc R U . . .
C5 C 0.0920(6) 0.3827(8) 0.4271(6) 0.122(4) Uani 1 1 d . . . . .
H5A H 0.074699 0.340399 0.386420 0.183 Uiso 1 1 calc R U . . .
H5B H 0.115171 0.433351 0.399774 0.183 Uiso 1 1 calc R U . . .
H5C H 0.040036 0.398152 0.459906 0.183 Uiso 1 1 calc R U . . .
C6 C 0.1294(6) 0.2678(7) 0.5158(7) 0.117(4) Uani 1 1 d . . . . .
H6A H 0.074191 0.278489 0.545796 0.176 Uiso 1 1 calc R U . . .
H6B H 0.174595 0.245440 0.553060 0.176 Uiso 1 1 calc R U . . .
H6C H 0.118169 0.226325 0.472637 0.176 Uiso 1 1 calc R U . . .
C7 C 0.1916(5) 0.3822(5) 0.2174(5) 0.071(2) Uani 1 1 d . . . . .
H7A H 0.205298 0.385402 0.159237 0.107 Uiso 1 1 calc R U . . .
H7B H 0.158384 0.432916 0.233764 0.107 Uiso 1 1 calc R U . . .
H7C H 0.155491 0.331517 0.228008 0.107 Uiso 1 1 calc R U . . .
C8 C 0.3698(6) 0.2966(5) 0.2217(5) 0.087(3) Uani 1 1 d . . . . .
H8A H 0.341203 0.240673 0.222928 0.130 Uiso 1 1 calc R U . . .
H8B H 0.428078 0.293203 0.248188 0.130 Uiso 1 1 calc R U . . .
H8C H 0.377453 0.314728 0.165147 0.130 Uiso 1 1 calc R U . . .
C9 C 0.3534(4) 0.4830(4) 0.2636(3) 0.0417(14) Uani 1 1 d . . . . .
C10 C 0.4397(5) 0.4930(5) 0.2371(4) 0.064(2) Uani 1 1 d . . . . .
H10 H 0.473347 0.444188 0.222592 0.077 Uiso 1 1 calc R U . . .
C11 C 0.4787(6) 0.5721(6) 0.2311(5) 0.082(3) Uani 1 1 d . . . . .
H11 H 0.538581 0.577272 0.213379 0.098 Uiso 1 1 calc R U . . .
C12 C 0.4311(7) 0.6426(6) 0.2507(5) 0.081(3) Uani 1 1 d . . . . .
H12 H 0.457546 0.697154 0.245628 0.097 Uiso 1 1 calc R U . . .
C13 C 0.3462(6) 0.6353(4) 0.2773(5) 0.067(2) Uani 1 1 d . . . . .
H13 H 0.313385 0.684629 0.291715 0.081 Uiso 1 1 calc R U . . .
C14 C 0.3079(5) 0.5569(4) 0.2835(4) 0.0502(16) Uani 1 1 d . . . . .
H14 H 0.248118 0.552859 0.302001 0.060 Uiso 1 1 calc R U . . .
I1 I 0.34615(3) 0.18036(3) 0.44864(3) 0.05887(18) Uani 1 1 d . . . . .
N1 N 0.3382(4) 0.4101(3) 0.5132(3) 0.0538(14) Uani 1 1 d . . . . .
N2 N 0.1612(4) 0.3470(4) 0.4800(4) 0.0605(16) Uani 1 1 d . . . . .
Si1 Si 0.29795(12) 0.37570(10) 0.27696(10) 0.0429(4) Uani 1 1 d . . . . .
Zn1 Zn 0.28463(4) 0.33464(4) 0.41583(4) 0.03728(19) 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
C1 N1 1.471(8) . ?
C2 N1 1.486(10) . ?
C3 C4 1.416(13) . ?
C3 N1 1.434(10) . ?
C4 N2 1.503(12) . ?
C5 N2 1.467(9) . ?
C6 N2 1.459(10) . ?
C7 Si1 1.878(7) . ?
C8 Si1 1.883(7) . ?
C9 C10 1.378(9) . ?
C9 C14 1.390(8) . ?
C9 Si1 1.896(6) . ?
C10 C11 1.380(10) . ?
C11 C12 1.359(11) . ?
C12 C13 1.354(11) . ?
C13 C14 1.366(9) . ?
I1 Zn1 2.6552(8) . ?
N1 Zn1 2.152(5) . ?
N2 Zn1 2.144(5) . ?
Si1 Zn1 2.3835(17) . ?

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
C4 C3 N1 114.5(8) . . ?
C3 C4 N2 115.3(8) . . ?
C10 C9 C14 116.2(6) . . ?
C10 C9 Si1 123.5(5) . . ?
C14 C9 Si1 120.2(5) . . ?
C9 C10 C11 121.7(7) . . ?
C12 C11 C10 119.9(8) . . ?
C13 C12 C11 120.2(8) . . ?
C12 C13 C14 119.9(8) . . ?
C13 C14 C9 122.2(7) . . ?
C3 N1 C1 112.3(7) . . ?
C3 N1 C2 108.2(7) . . ?
C1 N1 C2 106.4(6) . . ?
C3 N1 Zn1 104.7(5) . . ?
C1 N1 Zn1 110.4(4) . . ?
C2 N1 Zn1 114.9(5) . . ?
C6 N2 C5 109.6(7) . . ?
C6 N2 C4 111.3(8) . . ?
C5 N2 C4 108.0(8) . . ?
C6 N2 Zn1 113.8(5) . . ?
C5 N2 Zn1 110.8(5) . . ?
C4 N2 Zn1 103.0(5) . . ?
C7 Si1 C8 105.7(4) . . ?
C7 Si1 C9 105.3(3) . . ?
C8 Si1 C9 106.4(3) . . ?
C7 Si1 Zn1 116.4(3) . . ?
C8 Si1 Zn1 109.4(3) . . ?
C9 Si1 Zn1 112.96(18) . . ?
N2 Zn1 N1 84.6(2) . . ?
N2 Zn1 Si1 121.36(16) . . ?
N1 Zn1 Si1 122.21(15) . . ?
N2 Zn1 I1 106.51(16) . . ?
N1 Zn1 I1 102.94(15) . . ?
Si1 Zn1 I1 114.46(5) . . ?

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
N1 C3 C4 N2 51.0(13) . . . . ?
C14 C9 C10 C11 0.2(10) . . . . ?
Si1 C9 C10 C11 -177.5(6) . . . . ?
C9 C10 C11 C12 -0.8(12) . . . . ?
C10 C11 C12 C13 1.1(13) . . . . ?
C11 C12 C13 C14 -0.9(12) . . . . ?
C12 C13 C14 C9 0.3(11) . . . . ?
C10 C9 C14 C13 0.0(10) . . . . ?
Si1 C9 C14 C13 177.8(5) . . . . ?
C4 C3 N1 C1 82.9(10) . . . . ?
C4 C3 N1 C2 -160.0(9) . . . . ?
C4 C3 N1 Zn1 -37.0(10) . . . . ?
C3 C4 N2 C6 89.0(10) . . . . ?
C3 C4 N2 C5 -150.7(9) . . . . ?
C3 C4 N2 Zn1 -33.4(10) . . . . ?
C10 C9 Si1 C7 -127.0(6) . . . . ?
C14 C9 Si1 C7 55.3(6) . . . . ?
C10 C9 Si1 C8 -15.1(6) . . . . ?
C14 C9 Si1 C8 167.3(5) . . . . ?
C10 C9 Si1 Zn1 104.9(5) . . . . ?
C14 C9 Si1 Zn1 -72.7(5) . . . . ?

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
_geom_hbond_publ_flag
C2 H2C I1 0.98 3.12 3.691(8) 118.8 . yes

_refine_diff_density_max         0.830
_refine_diff_density_min         -0.804
_refine_diff_density_rms         0.101



####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2089062'
loop_
_audit_author_name
_audit_author_address
'Revathi C'
;Indian Institute of Science Education and Research
India
;
_audit_update_record             
;
2021-06-09 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H25 I N2 Si Zn'
_chemical_formula_sum            'C9 H25 I N2 Si Zn'
_chemical_formula_weight         381.67

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   19.6510(16)
_cell_length_b                   10.2987(8)
_cell_length_c                   8.2925(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1678.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6832
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      25.37

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.5112
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.095
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    3.351
_shelx_estimated_absorpt_T_min   0.741
_shelx_estimated_absorpt_T_max   0.878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.741
_exptl_absorpt_correction_T_max  0.878
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            25023
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.865
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2952
_reflns_number_gt                2482
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.859
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP3- 2014.1(Farrugia, 1997) '
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          
;
 Refined as a 2-component inversion 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)+(0.0324P)²+4.2072P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.03(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2952
_refine_ls_number_parameters     183
_refine_ls_number_restraints     76
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.0938
_refine_ls_wR_factor_gt          0.0881
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.027
_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
C1 C 0.2066(6) 0.416(2) 0.541(2) 0.172(10) Uani 1 1 d . . . . .
H1A H 0.216811 0.479479 0.626214 0.257 Uiso 1 1 calc R U . A 2
H1B H 0.164887 0.442287 0.484900 0.257 Uiso 1 1 calc R U . A 2
H1C H 0.200409 0.330275 0.588851 0.257 Uiso 1 1 calc R U . A 2
C2 C 0.2465(7) 0.3192(14) 0.3027(16) 0.104(5) Uani 1 1 d . . . . .
H2A H 0.284126 0.315890 0.225154 0.156 Uiso 1 1 calc R U . . .
H2B H 0.240217 0.233214 0.351146 0.156 Uiso 1 1 calc R U . . .
H2C H 0.204695 0.345226 0.247196 0.156 Uiso 1 1 calc R U . . .
C5 C 0.4363(9) 0.5374(16) 0.310(2) 0.139(8) Uani 1 1 d . . . . .
H5A H 0.416688 0.478764 0.229018 0.209 Uiso 1 1 calc R U . . .
H5B H 0.446444 0.621327 0.259411 0.209 Uiso 1 1 calc R U . . .
H5C H 0.478371 0.499531 0.352357 0.209 Uiso 1 1 calc R U . . .
C6 C 0.4173(10) 0.6433(13) 0.560(2) 0.129(6) Uani 1 1 d . . . . .
H6A H 0.461070 0.608341 0.596756 0.193 Uiso 1 1 calc R U . . .
H6B H 0.424342 0.728986 0.511795 0.193 Uiso 1 1 calc R U . . .
H6C H 0.386396 0.651103 0.652513 0.193 Uiso 1 1 calc R U . . .
I1 I 0.34011(5) 0.41125(11) 0.84847(12) 0.1070(4) Uani 1 1 d . . . . .
N2 N 0.2622(4) 0.4126(8) 0.4279(10) 0.056(2) Uani 1 1 d D U . . .
N1 N 0.3878(4) 0.5561(7) 0.4412(10) 0.056(2) Uani 1 1 d D . . . .
Zn1 Zn 0.35976(5) 0.36899(9) 0.53755(15) 0.0476(2) Uani 1 1 d . . . . .
C7 C 0.3857(13) 0.0284(17) 0.525(4) 0.130(11) Uani 0.733(17) 1 d D U P B 1
H7A H 0.337602 0.020728 0.495970 0.196 Uiso 0.733(17) 1 calc R U P B 1
H7B H 0.411021 -0.045391 0.480779 0.196 Uiso 0.733(17) 1 calc R U P B 1
H7C H 0.390176 0.028773 0.643013 0.196 Uiso 0.733(17) 1 calc R U P B 1
C9 C 0.5127(9) 0.191(5) 0.502(4) 0.109(12) Uani 0.733(17) 1 d D U P B 1
H9A H 0.533107 0.271298 0.460356 0.163 Uiso 0.733(17) 1 calc R U P B 1
H9B H 0.516140 0.190260 0.620036 0.163 Uiso 0.733(17) 1 calc R U P B 1
H9C H 0.536984 0.116096 0.457802 0.163 Uiso 0.733(17) 1 calc R U P B 1
C8 C 0.4220(9) 0.1570(19) 0.217(2) 0.092(7) Uani 0.733(17) 1 d D U P B 1
H8A H 0.375137 0.151965 0.176838 0.138 Uiso 0.733(17) 1 calc R U P B 1
H8B H 0.445543 0.229415 0.164405 0.138 Uiso 0.733(17) 1 calc R U P B 1
H8C H 0.445777 0.075674 0.192456 0.138 Uiso 0.733(17) 1 calc R U P B 1
C3 C 0.3247(8) 0.6237(16) 0.403(3) 0.089(7) Uani 0.733(17) 1 d D . P B 1
H3A H 0.333953 0.694392 0.325495 0.106 Uiso 0.733(17) 1 calc R U P B 1
H3B H 0.305776 0.662925 0.502686 0.106 Uiso 0.733(17) 1 calc R U P B 1
C4 C 0.2743(9) 0.5314(14) 0.333(3) 0.087(6) Uani 0.733(17) 1 d D U P B 1
H4A H 0.230432 0.577409 0.319793 0.104 Uiso 0.733(17) 1 calc R U P B 1
H4B H 0.290171 0.505810 0.224290 0.104 Uiso 0.733(17) 1 calc R U P B 1
Si1 Si 0.4210(4) 0.1835(7) 0.4414(11) 0.0551(17) Uani 0.733(17) 1 d D . P B 1
Si1' Si 0.4246(12) 0.181(2) 0.517(3) 0.060(4) Uani 0.267(17) 1 d D . P B 2
C7' C 0.381(3) 0.053(7) 0.398(10) 0.127(18) Uani 0.267(17) 1 d D U P B 2
H7'1 H 0.372871 0.083707 0.287844 0.190 Uiso 0.267(17) 1 calc R U P B 2
H7'2 H 0.408952 -0.025689 0.394964 0.190 Uiso 0.267(17) 1 calc R U P B 2
H7'3 H 0.336803 0.032050 0.448537 0.190 Uiso 0.267(17) 1 calc R U P B 2
C8' C 0.436(4) 0.111(7) 0.723(5) 0.15(3) Uani 0.267(17) 1 d D U P B 2
H8'1 H 0.459439 0.174283 0.791961 0.226 Uiso 0.267(17) 1 calc R U P B 2
H8'2 H 0.391845 0.089580 0.769163 0.226 Uiso 0.267(17) 1 calc R U P B 2
H8'3 H 0.463993 0.031842 0.715590 0.226 Uiso 0.267(17) 1 calc R U P B 2
C9' C 0.514(3) 0.196(13) 0.440(12) 0.10(2) Uani 0.267(17) 1 d D U P B 2
H9'1 H 0.537582 0.263589 0.501589 0.149 Uiso 0.267(17) 1 calc R U P B 2
H9'2 H 0.537236 0.113202 0.453013 0.149 Uiso 0.267(17) 1 calc R U P B 2
H9'3 H 0.512623 0.220302 0.325932 0.149 Uiso 0.267(17) 1 calc R U P B 2
C3' C 0.3296(13) 0.578(4) 0.336(4) 0.062(12) Uani 0.267(17) 1 d D U P B 2
H3'1 H 0.332703 0.518978 0.241516 0.075 Uiso 0.267(17) 1 calc R U P B 2
H3'2 H 0.330681 0.668312 0.295236 0.075 Uiso 0.267(17) 1 calc R U P B 2
C4' C 0.2623(17) 0.5539(13) 0.424(5) 0.051(9) Uani 0.267(17) 1 d D U P B 2
H4'1 H 0.262657 0.591645 0.533736 0.061 Uiso 0.267(17) 1 calc R U P B 2
H4'2 H 0.223020 0.588618 0.362878 0.061 Uiso 0.267(17) 1 calc R U P B 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
C1 N2 1.440(16) . ?
C1 C4' 2.04(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N2 1.448(14) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C5 N1 1.462(16) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 N1 1.455(17) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
I1 Zn1 2.6431(15) . ?
N2 C4' 1.456(13) . ?
N2 C4 1.474(11) . ?
N2 Zn1 2.169(8) . ?
N1 C3 1.455(11) . ?
N1 C3' 1.457(13) . ?
N1 Zn1 2.158(8) . ?
Zn1 Si1' 2.32(2) . ?
Zn1 Si1 2.395(7) . ?
C7 Si1 1.875(15) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 Si1 1.873(18) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C8 Si1 1.882(16) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C3 C4 1.492(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
Si1' C7' 1.86(2) . ?
Si1' C8' 1.87(2) . ?
Si1' C9' 1.87(2) . ?
C7' H7'1 0.9800 . ?
C7' H7'2 0.9800 . ?
C7' H7'3 0.9800 . ?
C8' H8'1 0.9800 . ?
C8' H8'2 0.9800 . ?
C8' H8'3 0.9800 . ?
C9' H9'1 0.9800 . ?
C9' H9'2 0.9800 . ?
C9' H9'3 0.9800 . ?
C3' C4' 1.53(3) . ?
C3' H3'1 0.9900 . ?
C3' H3'2 0.9900 . ?
C4' H4'1 0.9900 . ?
C4' H4'2 0.9900 . ?

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
N2 C1 C4' 45.7(9) . . ?
N2 C1 H1A 109.5 . . ?
C4' C1 H1A 76.9 . . ?
N2 C1 H1B 109.5 . . ?
C4' C1 H1B 92.0 . . ?
H1A C1 H1B 109.5 . . ?
N2 C1 H1C 109.5 . . ?
C4' C1 H1C 152.9 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 N2 C2 108.9(11) . . ?
C1 N2 C4' 89.3(17) . . ?
C2 N2 C4' 130.4(19) . . ?
C1 N2 C4 116.5(14) . . ?
C2 N2 C4 101.7(12) . . ?
C1 N2 Zn1 113.8(9) . . ?
C2 N2 Zn1 110.5(7) . . ?
C4' N2 Zn1 102.4(15) . . ?
C4 N2 Zn1 104.7(8) . . ?
C6 N1 C3 101.0(12) . . ?
C6 N1 C3' 129(2) . . ?
C6 N1 C5 109.1(12) . . ?
C3 N1 C5 117.3(15) . . ?
C3' N1 C5 94.8(19) . . ?
C6 N1 Zn1 113.6(8) . . ?
C3 N1 Zn1 106.8(9) . . ?
C3' N1 Zn1 99.2(17) . . ?
C5 N1 Zn1 109.0(8) . . ?
N1 Zn1 N2 83.4(3) . . ?
N1 Zn1 Si1' 125.3(7) . . ?
N2 Zn1 Si1' 128.8(6) . . ?
N1 Zn1 Si1 117.4(3) . . ?
N2 Zn1 Si1 118.0(3) . . ?
N1 Zn1 I1 104.6(2) . . ?
N2 Zn1 I1 104.2(2) . . ?
Si1' Zn1 I1 106.8(6) . . ?
Si1 Zn1 I1 122.0(2) . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
Si1 C9 H9A 109.5 . . ?
Si1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
Si1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
Si1 C8 H8A 109.5 . . ?
Si1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Si1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C3 C4 110.2(13) . . ?
N1 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
N1 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
N2 C4 C3 115.3(15) . . ?
N2 C4 H4A 108.4 . . ?
C3 C4 H4A 108.4 . . ?
N2 C4 H4B 108.4 . . ?
C3 C4 H4B 108.4 . . ?
H4A C4 H4B 107.5 . . ?
C9 Si1 C7 107.0(18) . . ?
C9 Si1 C8 105.2(13) . . ?
C7 Si1 C8 104.3(13) . . ?
C9 Si1 Zn1 111.1(13) . . ?
C7 Si1 Zn1 111.7(8) . . ?
C8 Si1 Zn1 116.8(7) . . ?
C7' Si1' C8' 106(4) . . ?
C7' Si1' C9' 108(4) . . ?
C8' Si1' C9' 103(4) . . ?
C7' Si1' Zn1 112(3) . . ?
C8' Si1' Zn1 109(3) . . ?
C9' Si1' Zn1 118(4) . . ?
Si1' C7' H7'1 109.5 . . ?
Si1' C7' H7'2 109.5 . . ?
H7'1 C7' H7'2 109.5 . . ?
Si1' C7' H7'3 109.5 . . ?
H7'1 C7' H7'3 109.5 . . ?
H7'2 C7' H7'3 109.5 . . ?
Si1' C8' H8'1 109.5 . . ?
Si1' C8' H8'2 109.5 . . ?
H8'1 C8' H8'2 109.5 . . ?
Si1' C8' H8'3 109.5 . . ?
H8'1 C8' H8'3 109.5 . . ?
H8'2 C8' H8'3 109.5 . . ?
Si1' C9' H9'1 109.5 . . ?
Si1' C9' H9'2 109.5 . . ?
H9'1 C9' H9'2 109.5 . . ?
Si1' C9' H9'3 109.5 . . ?
H9'1 C9' H9'3 109.5 . . ?
H9'2 C9' H9'3 109.5 . . ?
N1 C3' C4' 111(3) . . ?
N1 C3' H3'1 109.3 . . ?
C4' C3' H3'1 109.3 . . ?
N1 C3' H3'2 109.3 . . ?
C4' C3' H3'2 109.3 . . ?
H3'1 C3' H3'2 108.0 . . ?
N2 C4' C3' 100(2) . . ?
N2 C4' C1 45.0(10) . . ?
C3' C4' C1 144(2) . . ?
N2 C4' H4'1 111.8 . . ?
C3' C4' H4'1 111.8 . . ?
C1 C4' H4'1 80.7 . . ?
N2 C4' H4'2 111.8 . . ?
C3' C4' H4'2 111.8 . . ?
C1 C4' H4'2 94.3 . . ?
H4'1 C4' H4'2 109.5 . . ?

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
C4' C1 N2 C2 -132.9(19) . . . . ?
C4' C1 N2 Zn1 103.3(18) . . . . ?
C6 N1 C3 C4 -158.5(18) . . . . ?
C5 N1 C3 C4 83(2) . . . . ?
Zn1 N1 C3 C4 -39(2) . . . . ?
C1 N2 C4 C3 93(2) . . . . ?
C2 N2 C4 C3 -148.9(17) . . . . ?
Zn1 N2 C4 C3 -34(2) . . . . ?
N1 C3 C4 N2 52(3) . . . . ?
C6 N1 C3' C4' -81(3) . . . . ?
C5 N1 C3' C4' 159(3) . . . . ?
Zn1 N1 C3' C4' 49(3) . . . . ?
C1 N2 C4' C3' 168(2) . . . . ?
C2 N2 C4' C3' -77(3) . . . . ?
Zn1 N2 C4' C3' 54(2) . . . . ?
C2 N2 C4' C1 114.6(17) . . . . ?
Zn1 N2 C4' C1 -114.2(10) . . . . ?
N1 C3' C4' N2 -76(4) . . . . ?
N1 C3' C4' C1 -61(6) . . . . ?

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
_geom_hbond_publ_flag
C1 H1A^b I1 0.98 3.12 3.658(17) 115.8 . yes
C6 H6C I1 0.98 3.09 3.704(18) 121.8 . yes
C1 H1A^b I1 0.98 3.12 3.658(17) 115.8 . yes
C6 H6C I1 0.98 3.09 3.704(18) 121.8 . yes

_refine_diff_density_max         1.001
_refine_diff_density_min         -0.977
_refine_diff_density_rms         0.074



