# Electronic Supplementary Material (ESI) for Inorganic 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_Li2CdSnSe4
_database_code_depnum_ccdc_archive 'CCDC 1524808'
_audit_update_record             
;
2016-12-28 deposited with the CCDC.
2017-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Lithium cadmium tin selenide (2/1/1/4)'
_chemical_name_common            'Lithium cadmium tin selenide (2/1/1/4)'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'Cd Li2 Se4 Sn'
_chemical_formula_structural     'Li2 Cd Sn Se4'
_chemical_formula_weight         560.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   14.4508(3)
_cell_length_b                   8.3986(2)
_cell_length_c                   6.80320(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     825.68(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3696
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      27.13

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    4.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    23.125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0760
_exptl_absorpt_correction_T_max  0.2944
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10208
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.72
_diffrn_reflns_theta_max         27.18
_reflns_number_total             1817
_reflns_number_gt                1561
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalMaker (Palmer, 2010)'
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0490P)²+4.0418P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    .
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_number_reflns         1817
_refine_ls_number_parameters     63
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1023
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_restrained_S_all      1.162
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Li1 Li 0.1603(6) 0.5055(13) 0.254(6) 0.000(2) Uiso 1 1 d . . .
Li2 Li 0.0748(7) -0.2601(12) 0.746(4) 0.000(2) Uiso 1 1 d . . .
Cd1 Cd 0.16337(4) -0.00442(9) 0.2481(3) 0.0252(2) Uani 1 1 d . . .
Sn1 Sn 0.41402(3) -0.25260(6) 0.2498(2) 0.01375(17) Uani 1 1 d . . .
Se1 Se 0.07678(6) -0.25806(11) 0.37960(15) 0.0189(3) Uani 1 1 d . . .
Se2 Se 0.08753(6) 0.25702(11) 0.38026(14) 0.0193(3) Uani 1 1 d . . .
Se3 Se 0.16827(5) -0.00069(12) -0.14025(14) 0.0175(3) Uani 1 1 d . . .
Se4 Se 0.33591(5) -0.00527(12) 0.37607(13) 0.0167(3) 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
Li1 Se1 2.476(17) 1_565 ?
Li1 Se2 2.489(18) . ?
Li1 Se4 2.57(4) 4_554 ?
Li1 Se3 2.580(16) 4 ?
Li2 Se1 2.49(3) . ?
Li2 Se2 2.517(13) 2 ?
Li2 Se4 2.587(13) 4_545 ?
Li2 Se3 2.678(12) 1_556 ?
Cd1 Se2 2.6136(14) . ?
Cd1 Se1 2.6276(15) . ?
Cd1 Se4 2.6410(12) . ?
Cd1 Se3 2.643(3) . ?
Sn1 Se3 2.5130(11) 4_545 ?
Sn1 Se1 2.5140(11) 3_545 ?
Sn1 Se2 2.5153(17) 4_544 ?
Sn1 Se4 2.5154(11) . ?
Se1 Li1 2.476(17) 1_545 ?
Se1 Sn1 2.5140(11) 3_445 ?
Se2 Sn1 2.5153(17) 4 ?
Se2 Li2 2.517(13) 2_554 ?
Se3 Sn1 2.5130(11) 4_554 ?
Se3 Li1 2.580(16) 4_544 ?
Se3 Li2 2.678(12) 1_554 ?
Se4 Li1 2.57(4) 4_545 ?
Se4 Li2 2.587(13) 4_554 ?

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
Se1 Li1 Se2 110.3(10) 1_565 . ?
Se1 Li1 Se4 112.5(11) 1_565 4_554 ?
Se2 Li1 Se4 108.9(10) . 4_554 ?
Se1 Li1 Se3 112.8(10) 1_565 4 ?
Se2 Li1 Se3 107.0(9) . 4 ?
Se4 Li1 Se3 104.9(9) 4_554 4 ?
Se1 Li2 Se2 111.9(6) . 2 ?
Se1 Li2 Se4 110.0(6) . 4_545 ?
Se2 Li2 Se4 110.4(7) 2 4_545 ?
Se1 Li2 Se3 106.1(6) . 1_556 ?
Se2 Li2 Se3 110.9(6) 2 1_556 ?
Se4 Li2 Se3 107.3(6) 4_545 1_556 ?
Se2 Cd1 Se1 111.36(7) . . ?
Se2 Cd1 Se4 106.54(6) . . ?
Se1 Cd1 Se4 109.58(6) . . ?
Se2 Cd1 Se3 110.19(7) . . ?
Se1 Cd1 Se3 111.27(7) . . ?
Se4 Cd1 Se3 107.72(5) . . ?
Se3 Sn1 Se1 111.57(5) 4_545 3_545 ?
Se3 Sn1 Se2 108.66(5) 4_545 4_544 ?
Se1 Sn1 Se2 111.00(4) 3_545 4_544 ?
Se3 Sn1 Se4 111.76(5) 4_545 . ?
Se1 Sn1 Se4 105.69(4) 3_545 . ?
Se2 Sn1 Se4 108.11(5) 4_544 . ?
Li1 Se1 Li2 110.2(10) 1_545 . ?
Li1 Se1 Sn1 111.3(6) 1_545 3_445 ?
Li2 Se1 Sn1 109.9(2) . 3_445 ?
Li1 Se1 Cd1 107.5(5) 1_545 . ?
Li2 Se1 Cd1 110.6(2) . . ?
Sn1 Se1 Cd1 107.28(5) 3_445 . ?
Li1 Se2 Sn1 112.0(9) . 4 ?
Li1 Se2 Li2 105.1(6) . 2_554 ?
Sn1 Se2 Li2 110.8(6) 4 2_554 ?
Li1 Se2 Cd1 114.1(5) . . ?
Sn1 Se2 Cd1 108.70(7) 4 . ?
Li2 Se2 Cd1 105.9(3) 2_554 . ?
Sn1 Se3 Li1 110.8(5) 4_554 4_544 ?
Sn1 Se3 Cd1 107.14(5) 4_554 . ?
Li1 Se3 Cd1 107.7(9) 4_544 . ?
Sn1 Se3 Li2 110.5(3) 4_554 1_554 ?
Li1 Se3 Li2 114.8(5) 4_544 1_554 ?
Cd1 Se3 Li2 105.4(5) . 1_554 ?
Sn1 Se4 Li1 111.1(2) . 4_545 ?
Sn1 Se4 Li2 108.5(3) . 4_554 ?
Li1 Se4 Li2 107.7(6) 4_545 4_554 ?
Sn1 Se4 Cd1 108.26(5) . . ?
Li1 Se4 Cd1 110.5(2) 4_545 . ?
Li2 Se4 Cd1 110.9(3) 4_554 . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.18
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         3.934
_refine_diff_density_min         -1.519
_refine_diff_density_rms         0.416

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

data_asim_mono1
_database_code_depnum_ccdc_archive 'CCDC 1524708'
_audit_update_record             
;
2016-12-28 deposited with the CCDC.
2017-06-13 downloaded from the CCDC.
;
_audit_creation_date             2016-08-25
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'I, C28 H39 N4'
_chemical_formula_sum            'C28 H39 I N4'
_chemical_formula_weight         558.53
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   11.264(5)
_cell_length_b                   16.103(8)
_cell_length_c                   16.181(10)
_cell_angle_alpha                90
_cell_angle_beta                 110.13(3)
_cell_angle_gamma                90
_cell_volume                     2756(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1551
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      17.984
_cell_measurement_theta_min      2.308
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.184
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1378 before and 0.1100 after correction.
The Ratio of minimum to maximum transmission is 0.6329.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1795
_diffrn_reflns_av_unetI/netI     0.1849
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            29465
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.352
_diffrn_reflns_theta_min         2.304
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3072
_reflns_number_total             6104
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.651
_refine_diff_density_min         -1.350
_refine_diff_density_rms         0.147
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         6104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1602
_refine_ls_R_factor_gt           0.0684
_refine_ls_restrained_S_all      0.944
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0560P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1811
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C26(H26), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C13(H13), C25(H25), C15(H15), C12(H12), C16(H16), C24(H24), C21(H21),
 C22(H22)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C6(H6A,H6B,H6C), C5(H5A,H5B,H5C), C28(H28A,H28B,H28C),
 C10(H10A,H10B,H10C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C27(H27A,H27B,
 H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Patterson Methods, followed by a Tangent Expansion (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.038
;
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 0.29500(5) 0.77879(3) 0.71624(3) 0.03815(19) Uani 1 1 d . . . . .
N1 N 0.4216(6) 0.7204(3) 0.5486(4) 0.0276(13) Uani 1 1 d . . . . .
H1 H 0.4033 0.7354 0.5938 0.033 Uiso 1 1 calc R . . . .
N4 N 0.2766(6) 0.5786(3) 0.6119(4) 0.0284(14) Uani 1 1 d . . . . .
N2 N 0.3754(6) 0.6235(3) 0.4366(4) 0.0283(14) Uani 1 1 d . . . . .
N3 N 0.1353(6) 0.6376(3) 0.5024(4) 0.0312(15) Uani 1 1 d . . . . .
C11 C 0.3057(7) 0.5535(4) 0.3899(5) 0.0249(16) Uani 1 1 d . . . . .
C2 C 0.2568(7) 0.6233(4) 0.5383(5) 0.0245(15) Uani 1 1 d . . . . .
C14 C 0.1951(7) 0.4152(4) 0.2869(5) 0.0259(15) Uani 1 1 d . . . . .
C13 C 0.2869(7) 0.4058(4) 0.3696(5) 0.0258(16) Uani 1 1 d . . . . .
H13 H 0.3134 0.3526 0.3902 0.031 Uiso 1 1 calc R . . . .
C20 C 0.5142(7) 0.7684(4) 0.5304(5) 0.0239(15) Uani 1 1 d . . . . .
C25 C 0.5733(7) 0.7482(4) 0.4700(5) 0.0298(18) Uani 1 1 d . . . . .
H25 H 0.5510 0.6996 0.4373 0.036 Uiso 1 1 calc R . . . .
C1 C 0.3568(6) 0.6529(4) 0.5034(5) 0.0236(15) Uani 1 1 d . . . . .
C15 C 0.1567(7) 0.4949(4) 0.2579(5) 0.0305(17) Uani 1 1 d . . . . .
H15 H 0.0918 0.5028 0.2044 0.037 Uiso 1 1 calc R . . . .
C3 C 0.0713(7) 0.6030(4) 0.5536(5) 0.0318(18) Uani 1 1 d . . . . .
C12 C 0.3400(7) 0.4734(4) 0.4221(5) 0.0281(16) Uani 1 1 d . . . . .
H12 H 0.3980 0.4655 0.4785 0.034 Uiso 1 1 calc R . . . .
C26 C 0.7948(7) 0.9323(4) 0.4893(5) 0.0314(18) Uani 1 1 d . . . . .
H26 H 0.8277 0.9061 0.4469 0.038 Uiso 1 1 calc R . . . .
C4 C 0.1604(8) 0.5668(4) 0.6213(5) 0.0332(19) Uani 1 1 d . . . . .
C16 C 0.2150(7) 0.5641(4) 0.3087(5) 0.0309(18) Uani 1 1 d . . . . .
H16 H 0.1919 0.6174 0.2870 0.037 Uiso 1 1 calc R . . . .
C23 C 0.6997(7) 0.8738(4) 0.5044(5) 0.0327(18) Uani 1 1 d . . . . .
C24 C 0.6652(7) 0.8000(4) 0.4584(5) 0.0288(17) Uani 1 1 d . . . . .
H24 H 0.7044 0.7847 0.4187 0.035 Uiso 1 1 calc R . . . .
C17 C 0.1427(7) 0.3418(4) 0.2267(5) 0.0343(18) Uani 1 1 d . . . . .
H17 H 0.0691 0.3610 0.1776 0.041 Uiso 1 1 calc R . . . .
C9 C 0.0766(8) 0.6918(4) 0.4267(5) 0.0354(18) Uani 1 1 d . . . . .
H9A H -0.0045 0.6687 0.3912 0.043 Uiso 1 1 calc R . . . .
H9B H 0.1298 0.6939 0.3907 0.043 Uiso 1 1 calc R . . . .
C8 C 0.4196(8) 0.4592(4) 0.6773(6) 0.044(2) Uani 1 1 d . . . . .
H8A H 0.3988 0.4374 0.6188 0.066 Uiso 1 1 calc GR . . . .
H8B H 0.3663 0.4339 0.7055 0.066 Uiso 1 1 calc GR . . . .
H8C H 0.5065 0.4473 0.7105 0.066 Uiso 1 1 calc GR . . . .
C21 C 0.5469(7) 0.8425(4) 0.5758(5) 0.0345(19) Uani 1 1 d . . . . .
H21 H 0.5074 0.8580 0.6153 0.041 Uiso 1 1 calc R . . . .
C6 C 0.1465(8) 0.5265(5) 0.7019(6) 0.050(2) Uani 1 1 d . . . . .
H6A H 0.1644 0.4682 0.7017 0.074 Uiso 1 1 calc GR . . . .
H6B H 0.0617 0.5342 0.7012 0.074 Uiso 1 1 calc GR . . . .
H6C H 0.2048 0.5516 0.7539 0.074 Uiso 1 1 calc GR . . . .
C7 C 0.3991(8) 0.5522(4) 0.6729(5) 0.0381(19) Uani 1 1 d . . . . .
H7A H 0.4081 0.5722 0.7312 0.046 Uiso 1 1 calc R . . . .
H7B H 0.4649 0.5780 0.6557 0.046 Uiso 1 1 calc R . . . .
C5 C -0.0684(7) 0.6083(5) 0.5293(6) 0.047(2) Uani 1 1 d . . . . .
H5A H -0.0924 0.6648 0.5340 0.071 Uiso 1 1 calc GR . . . .
H5B H -0.0948 0.5741 0.5685 0.071 Uiso 1 1 calc GR . . . .
H5C H -0.1083 0.5893 0.4699 0.071 Uiso 1 1 calc GR . . . .
C22 C 0.6379(8) 0.8941(5) 0.5631(6) 0.044(2) Uani 1 1 d . . . . .
H22 H 0.6583 0.9435 0.5946 0.053 Uiso 1 1 calc R . . . .
C28 C 0.7352(9) 1.0134(5) 0.4505(6) 0.048(2) Uani 1 1 d . . . . .
H28A H 0.6676 1.0031 0.3961 0.072 Uiso 1 1 calc GR . . . .
H28B H 0.7975 1.0482 0.4399 0.072 Uiso 1 1 calc GR . . . .
H28C H 0.7023 1.0405 0.4909 0.072 Uiso 1 1 calc GR . . . .
C10 C 0.0570(9) 0.7796(4) 0.4546(6) 0.050(2) Uani 1 1 d . . . . .
H10A H 0.0160 0.8127 0.4033 0.075 Uiso 1 1 calc GR . . . .
H10B H 0.1374 0.8038 0.4873 0.075 Uiso 1 1 calc GR . . . .
H10C H 0.0052 0.7778 0.4909 0.075 Uiso 1 1 calc GR . . . .
C18 C 0.0997(9) 0.2702(5) 0.2727(6) 0.056(3) Uani 1 1 d . . . . .
H18A H 0.1702 0.2507 0.3215 0.084 Uiso 1 1 calc GR . . . .
H18B H 0.0674 0.2256 0.2317 0.084 Uiso 1 1 calc GR . . . .
H18C H 0.0345 0.2896 0.2936 0.084 Uiso 1 1 calc GR . . . .
C19 C 0.2425(9) 0.3121(5) 0.1890(6) 0.052(2) Uani 1 1 d . . . . .
H19A H 0.2672 0.3574 0.1600 0.078 Uiso 1 1 calc GR . . . .
H19B H 0.2080 0.2682 0.1475 0.078 Uiso 1 1 calc GR . . . .
H19C H 0.3150 0.2919 0.2359 0.078 Uiso 1 1 calc GR . . . .
C27 C 0.9067(8) 0.9475(5) 0.5744(7) 0.055(3) Uani 1 1 d . . . . .
H27A H 0.8777 0.9758 0.6161 0.082 Uiso 1 1 calc GR . . . .
H27B H 0.9689 0.9810 0.5618 0.082 Uiso 1 1 calc GR . . . .
H27C H 0.9437 0.8953 0.5985 0.082 Uiso 1 1 calc GR . . . .


_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
N1 H1 0.8600 . ?
N1 C20 1.409(8) . ?
N1 C1 1.372(8) . ?
N4 C2 1.342(8) . ?
N4 C4 1.382(9) . ?
N4 C7 1.457(10) . ?
N2 C11 1.432(8) . ?
N2 C1 1.262(8) . ?
N3 C2 1.310(9) . ?
N3 C3 1.387(9) . ?
N3 C9 1.464(9) . ?
C11 C12 1.395(9) . ?
C11 C16 1.370(10) . ?
C2 C1 1.501(9) . ?
C14 C13 1.390(10) . ?
C14 C15 1.384(9) . ?
C14 C17 1.516(9) . ?
C13 H13 0.9300 . ?
C13 C12 1.384(9) . ?
C20 C25 1.397(9) . ?
C20 C21 1.383(9) . ?
C25 H25 0.9300 . ?
C25 C24 1.392(9) . ?
C15 H15 0.9300 . ?
C15 C16 1.406(10) . ?
C3 C4 1.339(11) . ?
C3 C5 1.487(10) . ?
C12 H12 0.9300 . ?
C26 H26 0.9800 . ?
C26 C23 1.509(9) . ?
C26 C28 1.502(10) . ?
C26 C27 1.533(12) . ?
C4 C6 1.512(10) . ?
C16 H16 0.9300 . ?
C23 C24 1.385(9) . ?
C23 C22 1.396(10) . ?
C24 H24 0.9300 . ?
C17 H17 0.9800 . ?
C17 C18 1.539(10) . ?
C17 C19 1.529(10) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.523(10) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C8 C7 1.512(9) . ?
C21 H21 0.9300 . ?
C21 C22 1.388(9) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C22 H22 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

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
C20 N1 H1 115.9 . . ?
C1 N1 H1 115.9 . . ?
C1 N1 C20 128.3(6) . . ?
C2 N4 C4 107.2(6) . . ?
C2 N4 C7 126.0(6) . . ?
C4 N4 C7 126.7(6) . . ?
C1 N2 C11 121.7(6) . . ?
C2 N3 C3 110.1(6) . . ?
C2 N3 C9 125.3(6) . . ?
C3 N3 C9 124.1(6) . . ?
C12 C11 N2 120.0(7) . . ?
C16 C11 N2 120.0(6) . . ?
C16 C11 C12 119.5(7) . . ?
N4 C2 C1 125.9(6) . . ?
N3 C2 N4 108.5(6) . . ?
N3 C2 C1 125.6(6) . . ?
C13 C14 C17 122.0(6) . . ?
C15 C14 C13 118.1(6) . . ?
C15 C14 C17 119.9(7) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 C14 121.7(6) . . ?
C12 C13 H13 119.1 . . ?
C25 C20 N1 125.8(6) . . ?
C21 C20 N1 116.3(6) . . ?
C21 C20 C25 117.9(6) . . ?
C20 C25 H25 119.6 . . ?
C24 C25 C20 120.7(6) . . ?
C24 C25 H25 119.6 . . ?
N1 C1 C2 112.4(6) . . ?
N2 C1 N1 122.6(6) . . ?
N2 C1 C2 124.8(6) . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.5(7) . . ?
C16 C15 H15 119.7 . . ?
N3 C3 C5 122.7(7) . . ?
C4 C3 N3 105.4(6) . . ?
C4 C3 C5 131.9(7) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.5(7) . . ?
C13 C12 H12 120.2 . . ?
C23 C26 H26 107.8 . . ?
C23 C26 C27 111.4(7) . . ?
C28 C26 H26 107.8 . . ?
C28 C26 C23 111.7(7) . . ?
C28 C26 C27 110.3(6) . . ?
C27 C26 H26 107.8 . . ?
N4 C4 C6 122.5(8) . . ?
C3 C4 N4 108.8(6) . . ?
C3 C4 C6 128.5(7) . . ?
C11 C16 C15 120.4(7) . . ?
C11 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C24 C23 C26 122.1(6) . . ?
C24 C23 C22 117.0(6) . . ?
C22 C23 C26 120.8(6) . . ?
C25 C24 H24 119.1 . . ?
C23 C24 C25 121.7(6) . . ?
C23 C24 H24 119.1 . . ?
C14 C17 H17 108.0 . . ?
C14 C17 C18 113.0(7) . . ?
C14 C17 C19 108.9(6) . . ?
C18 C17 H17 108.0 . . ?
C19 C17 H17 108.0 . . ?
C19 C17 C18 110.8(6) . . ?
N3 C9 H9A 109.2 . . ?
N3 C9 H9B 109.2 . . ?
N3 C9 C10 112.0(6) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
C20 C21 H21 119.5 . . ?
C20 C21 C22 120.9(6) . . ?
C22 C21 H21 119.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N4 C7 C8 114.5(7) . . ?
N4 C7 H7A 108.6 . . ?
N4 C7 H7B 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C23 C22 H22 119.1 . . ?
C21 C22 C23 121.8(7) . . ?
C21 C22 H22 119.1 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
N1 C20 C25 C24 -179.1(7) . . . . ?
N1 C20 C21 C22 179.5(7) . . . . ?
N4 C2 C1 N1 -77.1(8) . . . . ?
N4 C2 C1 N2 107.4(9) . . . . ?
N2 C11 C12 C13 -169.0(6) . . . . ?
N2 C11 C16 C15 172.5(6) . . . . ?
N3 C2 C1 N1 102.1(8) . . . . ?
N3 C2 C1 N2 -73.4(10) . . . . ?
N3 C3 C4 N4 -0.2(8) . . . . ?
N3 C3 C4 C6 173.7(7) . . . . ?
C11 N2 C1 N1 -179.3(6) . . . . ?
C11 N2 C1 C2 -4.3(11) . . . . ?
C2 N4 C4 C3 0.8(8) . . . . ?
C2 N4 C4 C6 -173.6(7) . . . . ?
C2 N4 C7 C8 -114.5(7) . . . . ?
C2 N3 C3 C4 -0.5(8) . . . . ?
C2 N3 C3 C5 -179.4(6) . . . . ?
C2 N3 C9 C10 -93.9(8) . . . . ?
C14 C13 C12 C11 -3.4(10) . . . . ?
C14 C15 C16 C11 -3.8(10) . . . . ?
C13 C14 C15 C16 4.0(10) . . . . ?
C13 C14 C17 C18 50.0(10) . . . . ?
C13 C14 C17 C19 -73.6(9) . . . . ?
C20 N1 C1 N2 1.0(12) . . . . ?
C20 N1 C1 C2 -174.6(6) . . . . ?
C20 C25 C24 C23 -1.3(12) . . . . ?
C20 C21 C22 C23 0.2(13) . . . . ?
C25 C20 C21 C22 -1.6(12) . . . . ?
C1 N1 C20 C25 -11.0(12) . . . . ?
C1 N1 C20 C21 167.8(7) . . . . ?
C1 N2 C11 C12 -79.8(9) . . . . ?
C1 N2 C11 C16 107.7(8) . . . . ?
C15 C14 C13 C12 -0.4(10) . . . . ?
C15 C14 C17 C18 -133.6(7) . . . . ?
C15 C14 C17 C19 102.8(8) . . . . ?
C3 N3 C2 N4 1.0(8) . . . . ?
C3 N3 C2 C1 -178.3(6) . . . . ?
C3 N3 C9 C10 77.0(9) . . . . ?
C12 C11 C16 C15 -0.1(10) . . . . ?
C26 C23 C24 C25 -177.1(7) . . . . ?
C26 C23 C22 C21 177.7(8) . . . . ?
C4 N4 C2 N3 -1.1(7) . . . . ?
C4 N4 C2 C1 178.2(6) . . . . ?
C4 N4 C7 C8 69.6(9) . . . . ?
C16 C11 C12 C13 3.6(10) . . . . ?
C24 C23 C22 C21 0.6(13) . . . . ?
C17 C14 C13 C12 176.0(6) . . . . ?
C17 C14 C15 C16 -172.6(6) . . . . ?
C9 N3 C2 N4 173.0(6) . . . . ?
C9 N3 C2 C1 -6.3(11) . . . . ?
C9 N3 C3 C4 -172.6(6) . . . . ?
C9 N3 C3 C5 8.6(10) . . . . ?
C21 C20 C25 C24 2.1(11) . . . . ?
C7 N4 C2 N3 -177.6(6) . . . . ?
C7 N4 C2 C1 1.7(11) . . . . ?
C7 N4 C4 C3 177.3(6) . . . . ?
C7 N4 C4 C6 3.0(10) . . . . ?
C5 C3 C4 N4 178.5(7) . . . . ?
C5 C3 C4 C6 -7.6(14) . . . . ?
C22 C23 C24 C25 -0.1(12) . . . . ?
C28 C26 C23 C24 114.1(8) . . . . ?
C28 C26 C23 C22 -62.8(10) . . . . ?
C27 C26 C23 C24 -122.0(8) . . . . ?
C27 C26 C23 C22 61.1(10) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
