# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_afm15pt3_11_P31c
_database_code_depnum_ccdc_archive 'CCDC 1416613'
_audit_update_record             
;
2015-08-03 deposited with the CCDC.
2015-09-16 downloaded from the CCDC.
;


# start Validation Reply Form
_vrf_SHFSU01_afm15pt3_11_P31c    
;
PROBLEM: The absolute value of parameter shift to su ratio > 0.20
RESPONSE: 

Failure to converge is associated with the eveidently highly 
disordered N-heptyl, N-methylpyrolidine cation

;
_vrf_PLAT080_afm15pt3_11_P31c    
;
PROBLEM: Maximum Shift/Error ............................       1.22 Why ? 
RESPONSE:
Failure to converge is associated with the eveidently highly 
disordered N-heptyl, N-methylpyrolidine cation
;
_vrf_PLAT411_afm15pt3_11_P31c    
;
PROBLEM: Short Inter H...H Contact  H3B    ..  H10D    ..       1.78 Ang.  
RESPONSE:
Disordered parts
;
_vrf_PLAT341_afm15pt3_11_P31c    
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0600 Ang.  
RESPONSE: 
High level of disorder
;
_vrf_PLAT410_afm15pt3_11_P31c    
;
PROBLEM: Short Intra H...H Contact  H1A    ..  H6A     ..       1.87 Ang.  
RESPONSE: 
High level of disorder
;
_vrf_PLAT413_afm15pt3_11_P31c    
;
PROBLEM: Short Inter XH3 .. XHn     H3A    ..  H11D    ..       1.98 Ang.  
RESPONSE: 
Disordered parts
;
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H72 Br7 N3 Zn2'
_chemical_formula_weight         1201.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           159
_space_group_name_H-M_alt        'P 3 1 c'
_space_group_name_Hall           'P 3 -2c'
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   'P 3 1 c'
_symmetry_space_group_name_Hall  'P 3 -2c'
_symmetry_Int_Tables_number      159


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

_cell_length_a                   14.7234(2)
_cell_length_b                   14.7234(2)
_cell_length_c                   12.4759(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2342.17(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    15448
_cell_measurement_theta_min      4.9290
_cell_measurement_theta_max      73.2910

_exptl_crystal_description       tablet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_F_000             1192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.033
_exptl_absorpt_coefficient_mu    8.429
_exptl_absorpt_correction_T_min  0.616
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  CrysAlisPro, Agilent Technologies,
  Version 1.171.36.28
  Empirical absorption correction using spherical 
  harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_crystal_treatment        
;
attached with Exxon Paratone N to a nylon loop and quenched 
in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. 
;

_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.5861
_diffrn_reflns_number            50065
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.466
_diffrn_reflns_theta_max         76.846
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3280
_reflns_number_gt                2634
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.990
_reflns_Friedel_fraction_max     0.997
_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.
;

_computing_data_collection       
;
  CrysAlisPro, Agilent Technologies,
;
_computing_cell_refinement       
;
  CrysAlisPro, Agilent Technologies,
;
_computing_data_reduction        
;
  CrysAlisPro, Agilent Technologies,
;
_computing_structure_solution    'ShelxT (sheldrick, 2013)'

_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014a)'

_computing_molecular_graphics    
;
  ORTEP3 for Windows (Farrugia, L., 1997)
  ORTEPIII  (Burnett, N.M., Johnson,C.K., 1996). 
  WinGX (Farrugia, 1999)
  shelXle (Hbschle,C.B., et al., 2011) 
;

_refine_special_details          
;
 Refined as a 4-component inversion twin with the secondary component, 
primary inverted component and secondary inverted component fractions
refining to 0.18, 0.19 and 0.32 respecitively.

Rigid body (SHELXL FRAG) refinement was used for the N-methyl-pyrolidine 
cation moiety and restraints were imposed on the remainder of the penedant 
hexyl residue of the N,N-hexyl-methyl-pyrolidine cation.

The refinement of the rigid body did not completey converge, oscillating 
as follows:

Mean shift/esd =   0.148  Maximum =     1.380 for rotX N1       
Max. shift = 0.266 A for H1B      Max. dU = 0.003 for C8A_a

and

Mean shift/esd =   0.143  Maximum =    -1.221 for rotZ N1       
Max. shift = 0.240 A for H1A      Max. dU =-0.003 for C8A_a


;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.08P)²+1.0P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00066(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Twinning involves inversion, so Flack parameter cannot be determined
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3280
_refine_ls_number_parameters     141
_refine_ls_number_restraints     170
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1646
_refine_ls_wR_factor_gt          0.1512
_refine_ls_goodness_of_fit_ref   1.234
_refine_ls_restrained_S_all      1.227
_refine_ls_shift/su_max          1.221
_refine_ls_shift/su_mean         0.144

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
Br1 Br 0.6177(4) 0.3131(10) 0.3430(9) 0.1222(18) Uani 0.3333 1 d . U P . .
Br2 Br 0.4884(2) 0.2345(3) 0.5857(3) 0.1020(9) Uani 1 1 d . U . . .
Br3 Br 0.4881(2) 0.2332(3) 0.0988(3) 0.0996(9) Uani 1 1 d . U . . .
Zn1 Zn 0.6667 0.3333 0.5361(5) 0.0703(15) Uani 1 3 d S TU P . .
Zn2 Zn 0.6667 0.3333 0.1497(5) 0.0724(18) Uani 1 3 d S TU P . .
N1 N 0.4839(16) 0.5178(15) 0.3458(19) 0.117(3) Uani 1 1 d G U . . .
C1 C 0.466(3) 0.440(2) 0.2571(19) 0.142(5) Uani 1 1 d G U . . .
H1A H 0.5243 0.4251 0.2530 0.170 Uiso 1 1 calc R U . . .
H1B H 0.4578 0.4663 0.1867 0.170 Uiso 1 1 calc R U . . .
C2 C 0.358(4) 0.338(3) 0.294(3) 0.165(7) Uani 1 1 d . U . . .
H2A H 0.2971 0.3300 0.2532 0.198 Uiso 1 1 calc R U . . .
H2B H 0.3621 0.2728 0.2873 0.198 Uiso 1 1 calc R U . . .
C3 C 0.354(4) 0.365(4) 0.410(4) 0.165(7) Uani 1 1 d . U . . .
H3A H 0.3383 0.3037 0.4546 0.198 Uiso 1 1 calc R U . . .
H3B H 0.2964 0.3804 0.4185 0.198 Uiso 1 1 calc R U . . .
C4 C 0.460(3) 0.463(3) 0.451(2) 0.142(5) Uani 1 1 d . U . . .
H4A H 0.4482 0.5020 0.5089 0.170 Uiso 1 1 calc R U . . .
H4B H 0.5129 0.4442 0.4732 0.170 Uiso 1 1 calc R U . . .
C5 C 0.4229(18) 0.5717(17) 0.335(2) 0.103(4) Uani 1 1 d . U . . .
H5A H 0.3542 0.5235 0.3041 0.155 Uiso 1 1 calc R U . . .
H5B H 0.4605 0.6329 0.2883 0.155 Uiso 1 1 calc R U . . .
H5C H 0.4136 0.5946 0.4060 0.155 Uiso 1 1 calc R U . . .
C6 C 0.600(2) 0.592(2) 0.309(2) 0.151(8) Uani 1 1 d D U . . .
H6A H 0.6366 0.5520 0.3010 0.181 Uiso 1 1 calc R U . . .
H6B H 0.6003 0.6238 0.2385 0.181 Uiso 1 1 calc R U . . .
C7 C 0.654(2) 0.677(3) 0.391(3) 0.180(12) Uani 1 1 d D U . . .
H7A H 0.6251 0.6500 0.4634 0.216 Uiso 1 1 calc R U . A 1
H7B H 0.6435 0.7370 0.3751 0.216 Uiso 1 1 calc R U . A 1
C8A C 0.769(3) 0.712(9) 0.389(6) 0.22(3) Uani 0.4 1 d D U P B 1
H8A1 H 0.7774 0.6494 0.3837 0.266 Uiso 0.4 1 calc R U P B 1
H8A2 H 0.8007 0.7547 0.3233 0.266 Uiso 0.4 1 calc R U P B 1
C9A C 0.827(3) 0.775(7) 0.485(6) 0.246(17) Uani 0.4 1 d D U P B 1
H9A1 H 0.8537 0.7357 0.5269 0.295 Uiso 0.4 1 calc R U P B 1
H9A2 H 0.8887 0.8417 0.4616 0.295 Uiso 0.4 1 calc R U P B 1
C10A C 0.760(4) 0.799(7) 0.557(5) 0.246(17) Uani 0.4 1 d D U P B 1
H10A H 0.7127 0.7360 0.5988 0.295 Uiso 0.4 1 calc R U P B 1
H10B H 0.7158 0.8174 0.5119 0.295 Uiso 0.4 1 calc R U P B 1
C11A C 0.823(8) 0.888(7) 0.633(7) 0.246(17) Uani 0.4 1 d D U P B 1
H11A H 0.7756 0.9010 0.6774 0.369 Uiso 0.4 1 calc R U P B 1
H11B H 0.8658 0.8705 0.6788 0.369 Uiso 0.4 1 calc R U P B 1
H11C H 0.8690 0.9519 0.5918 0.369 Uiso 0.4 1 calc R U P B 1
C8B C 0.766(3) 0.751(3) 0.358(5) 0.203(17) Uani 0.6 1 d D U P B 2
H8B1 H 0.8016 0.7096 0.3469 0.244 Uiso 0.6 1 calc R U P B 2
H8B2 H 0.7660 0.7837 0.2891 0.244 Uiso 0.6 1 calc R U P B 2
C9B C 0.826(3) 0.835(3) 0.440(7) 0.246(17) Uani 0.6 1 d D U P B 2
H9B1 H 0.9017 0.8706 0.4214 0.295 Uiso 0.6 1 calc R U P B 2
H9B2 H 0.8171 0.8023 0.5111 0.295 Uiso 0.6 1 calc R U P B 2
C10B C 0.791(5) 0.915(4) 0.445(5) 0.246(17) Uani 0.6 1 d D U P B 2
H10C H 0.8124 0.9568 0.3778 0.295 Uiso 0.6 1 calc R U P B 2
H10D H 0.7140 0.8786 0.4497 0.295 Uiso 0.6 1 calc R U P B 2
C11B C 0.837(8) 0.988(6) 0.539(6) 0.246(17) Uani 0.6 1 d D U P B 2
H11D H 0.8125 1.0387 0.5385 0.369 Uiso 0.6 1 calc R U P B 2
H11E H 0.8157 0.9477 0.6055 0.369 Uiso 0.6 1 calc R U P B 2
H11F H 0.9142 1.0259 0.5337 0.369 Uiso 0.6 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
Br1 Br1 1.086(8) 2_655 ?
Br1 Br1 1.086(8) 3_665 ?
Br1 Zn1 2.490(11) . ?
Br1 Zn2 2.492(11) . ?
Br2 Zn1 2.360(3) . ?
Br3 Zn2 2.369(3) . ?
Zn1 Br2 2.360(3) 2_655 ?
Zn1 Br2 2.360(3) 3_665 ?
Zn1 Br1 2.490(11) 2_655 ?
Zn1 Br1 2.490(11) 3_665 ?
Zn2 Br3 2.369(3) 2_655 ?
Zn2 Br3 2.369(3) 3_665 ?
Zn2 Br1 2.492(11) 2_655 ?
Zn2 Br1 2.492(11) 3_665 ?
N1 C5 1.471(15) . ?
N1 C4 1.49(3) . ?
N1 C1 1.5169 . ?
N1 C6 1.57(3) . ?
C1 C2 1.62(6) . ?
C2 C3 1.50(5) . ?
C3 C4 1.59(7) . ?
C6 C7 1.504(7) . ?
C7 C8A 1.505(10) . ?
C7 C8B 1.505(10) . ?
C8A C9A 1.504(10) . ?
C9A C10A 1.504(10) . ?
C10A C11A 1.504(10) . ?
C8B C9B 1.504(10) . ?
C9B C10B 1.504(10) . ?
C10B C11B 1.504(10) . ?

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
Br1 Br1 Br1 60.003(4) 2_655 3_665 ?
Br1 Br1 Zn1 77.40(10) 2_655 . ?
Br1 Br1 Zn1 77.40(10) 3_665 . ?
Br1 Br1 Zn2 77.41(12) 2_655 . ?
Br1 Br1 Zn2 77.41(12) 3_665 . ?
Zn1 Br1 Zn2 150.8(2) . . ?
Br2 Zn1 Br2 113.38(13) . 2_655 ?
Br2 Zn1 Br2 113.38(13) . 3_665 ?
Br2 Zn1 Br2 113.38(13) 2_655 3_665 ?
Br2 Zn1 Br1 109.9(3) . 2_655 ?
Br2 Zn1 Br1 90.80(17) 2_655 2_655 ?
Br2 Zn1 Br1 114.1(3) 3_665 2_655 ?
Br2 Zn1 Br1 90.80(17) . . ?
Br2 Zn1 Br1 114.1(3) 2_655 . ?
Br2 Zn1 Br1 109.9(3) 3_665 . ?
Br1 Zn1 Br1 25.20(19) 2_655 . ?
Br2 Zn1 Br1 114.1(3) . 3_665 ?
Br2 Zn1 Br1 109.9(3) 2_655 3_665 ?
Br2 Zn1 Br1 90.80(17) 3_665 3_665 ?
Br1 Zn1 Br1 25.20(19) 2_655 3_665 ?
Br1 Zn1 Br1 25.20(19) . 3_665 ?
Br3 Zn2 Br3 113.09(13) 2_655 3_665 ?
Br3 Zn2 Br3 113.09(13) 2_655 . ?
Br3 Zn2 Br3 113.09(13) 3_665 . ?
Br3 Zn2 Br1 91.17(19) 2_655 2_655 ?
Br3 Zn2 Br1 114.5(3) 3_665 2_655 ?
Br3 Zn2 Br1 110.1(3) . 2_655 ?
Br3 Zn2 Br1 114.5(3) 2_655 . ?
Br3 Zn2 Br1 110.1(3) 3_665 . ?
Br3 Zn2 Br1 91.17(19) . . ?
Br1 Zn2 Br1 25.2(2) 2_655 . ?
Br3 Zn2 Br1 110.1(3) 2_655 3_665 ?
Br3 Zn2 Br1 91.17(19) 3_665 3_665 ?
Br3 Zn2 Br1 114.5(3) . 3_665 ?
Br1 Zn2 Br1 25.2(2) 2_655 3_665 ?
Br1 Zn2 Br1 25.2(2) . 3_665 ?
C5 N1 C4 109(2) . . ?
C5 N1 C1 114.7(18) . . ?
C4 N1 C1 109(2) . . ?
C5 N1 C6 109.9(18) . . ?
C4 N1 C6 121(2) . . ?
C1 N1 C6 92(2) . . ?
N1 C1 C2 102(2) . . ?
C3 C2 C1 100(4) . . ?
C2 C3 C4 114(5) . . ?
N1 C4 C3 94(3) . . ?
C7 C6 N1 109(2) . . ?
C6 C7 C8A 108(3) . . ?
C6 C7 C8B 110(3) . . ?
C9A C8A C7 112.8(14) . . ?
C10A C9A C8A 112.6(14) . . ?
C9A C10A C11A 112.8(15) . . ?
C9B C8B C7 112.9(14) . . ?
C8B C9B C10B 112.7(14) . . ?
C11B C10B C9B 112.8(14) . . ?

_refine_diff_density_max         0.971
_refine_diff_density_min         -0.756
_refine_diff_density_rms         0.095

####################################################################### 
# 
# 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_afm13pt9
_database_code_depnum_ccdc_archive 'CCDC 1416614'
_audit_update_record             
;
2015-08-03 deposited with the CCDC.
2015-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H40 Br6 N2 Zn2'
_chemical_formula_weight         870.70

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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                   8.9131(10)
_cell_length_b                   10.4346(12)
_cell_length_c                   15.6895(19)
_cell_angle_alpha                90
_cell_angle_beta                 104.580(7)
_cell_angle_gamma                90
_cell_volume                     1412.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8162
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      28.10

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.089
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.053
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.048
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    10.192
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.846
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
 SADABS (Sheldrick, 1996)
;


_diffrn_crystal_treatment        
;
attached with Exxon Paratone N to a nylon loop. 
The crystal was quenched in a cold nitrogen gas stream from an 
Oxford Cryosystems Cryostream.
;


_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  APEXII-FR591
_diffrn_measurement_method       ω+φ
_diffrn_reflns_number            61940
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_av_R_equivalents  0.0911
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.368
_diffrn_reflns_theta_max         28.426
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3528
_reflns_number_gt                2915
_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       'APEX (Bruker-AXS,2012)'
_computing_cell_refinement       'SAINT (Bruker-AXS,2012)'
_computing_data_reduction        'SAINT and XPREP (Bruker-AXS,2012)'
_computing_structure_solution    'SIR97 (Altomare, et. al. 1997)'
_computing_structure_refinement  'SHELXL-14 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
  xtal 3.6 (Hall,du Boulay, D.J. & Olthof-Hazekamp, R. 1999)
  ORTEPII  (Johnson,C.K., 1976). 
  WinGX (Farrugia, 1999)
  shelXle (Hbschle,C.B., et al., 2011) 
;
_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)+(0.1P)²+5.0P] 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         3528
_refine_ls_number_parameters     122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1637
_refine_ls_wR_factor_gt          0.1439
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_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
Br1 Br 0.64944(8) 0.11278(6) -0.00972(4) 0.02948(19) Uani 1 1 d . . . . .
Br2 Br 0.23381(7) 0.25563(6) -0.00887(4) 0.02775(19) Uani 1 1 d . . . . .
Br3 Br 0.51645(7) 0.12403(6) 0.21185(4) 0.02517(18) Uani 1 1 d . . . . .
Zn1 Zn 0.42744(7) 0.10915(6) 0.05746(4) 0.01782(18) Uani 1 1 d . . . . .
N1 N 0.0555(5) 0.0781(4) 0.2778(3) 0.0148(8) Uani 1 1 d . . . . .
C1 C 0.2050(6) 0.0142(5) 0.3261(4) 0.0196(11) Uani 1 1 d . . . . .
H1A H 0.2715 0.0043 0.2846 0.024 Uiso 1 1 calc R U . . .
H1B H 0.1803 -0.0728 0.3437 0.024 Uiso 1 1 calc R U . . .
C2 C 0.2970(7) 0.0836(7) 0.4072(4) 0.0282(13) Uani 1 1 d . . . . .
H2A H 0.2323 0.0954 0.4487 0.042 Uiso 1 1 calc R U . . .
H2B H 0.3298 0.1674 0.3902 0.042 Uiso 1 1 calc R U . . .
H2C H 0.3886 0.0328 0.4353 0.042 Uiso 1 1 calc R U . . .
C3 C 0.0919(6) 0.2097(5) 0.2471(4) 0.0225(11) Uani 1 1 d . . . . .
H3A H 0.1754 0.2008 0.2162 0.027 Uiso 1 1 calc R U . . .
H3B H 0.1322 0.2642 0.2996 0.027 Uiso 1 1 calc R U . . .
C4 C -0.0445(8) 0.2781(6) 0.1863(5) 0.0359(16) Uani 1 1 d . . . . .
H4A H -0.1289 0.2865 0.2157 0.054 Uiso 1 1 calc R U . . .
H4B H -0.0807 0.2284 0.1320 0.054 Uiso 1 1 calc R U . . .
H4C H -0.0120 0.3635 0.1720 0.054 Uiso 1 1 calc R U . . .
C5 C -0.0231(6) -0.0059(5) 0.1997(3) 0.0179(10) Uani 1 1 d . . . . .
H5A H -0.1276 0.0292 0.1729 0.021 Uiso 1 1 calc R U . . .
H5B H -0.0368 -0.0931 0.2216 0.021 Uiso 1 1 calc R U . . .
C6 C 0.0662(7) -0.0161(6) 0.1284(4) 0.0278(13) Uani 1 1 d . . . . .
H6A H 0.1679 -0.0548 0.1535 0.042 Uiso 1 1 calc R U . . .
H6B H 0.0800 0.0697 0.1061 0.042 Uiso 1 1 calc R U . . .
H6C H 0.0078 -0.0696 0.0800 0.042 Uiso 1 1 calc R U . . .
C7 C -0.0547(6) 0.0939(6) 0.3368(4) 0.0219(11) Uani 1 1 d . . . . .
H7A H -0.0085 0.1555 0.3841 0.026 Uiso 1 1 calc R U . . .
H7B H -0.1526 0.1318 0.3016 0.026 Uiso 1 1 calc R U . . .
C8 C -0.0926(7) -0.0280(6) 0.3786(4) 0.0284(13) Uani 1 1 d . . . . .
H8A H 0.0009 -0.0600 0.4204 0.043 Uiso 1 1 calc R U . . .
H8B H -0.1304 -0.0924 0.3329 0.043 Uiso 1 1 calc R U . . .
H8C H -0.1728 -0.0106 0.4099 0.043 Uiso 1 1 calc R U . . .


_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
Br1 Zn1 2.4653(9) . ?
Br1 Zn1 2.4768(9) 3_655 ?
Br2 Zn1 2.3439(9) . ?
Br3 Zn1 2.3566(9) . ?
Zn1 Br1 2.4769(9) 3_655 ?
N1 C1 1.512(6) . ?
N1 C3 1.518(7) . ?
N1 C7 1.518(7) . ?
N1 C5 1.525(6) . ?
C1 C2 1.514(8) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.521(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.531(8) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.508(9) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
Zn1 Br1 Zn1 85.66(3) . 3_655 ?
Br2 Zn1 Br3 115.67(3) . . ?
Br2 Zn1 Br1 112.37(3) . . ?
Br3 Zn1 Br1 109.86(3) . . ?
Br2 Zn1 Br1 111.02(3) . 3_655 ?
Br3 Zn1 Br1 111.62(3) . 3_655 ?
Br1 Zn1 Br1 94.35(3) . 3_655 ?
C1 N1 C3 109.0(4) . . ?
C1 N1 C7 111.5(4) . . ?
C3 N1 C7 108.5(4) . . ?
C1 N1 C5 108.5(4) . . ?
C3 N1 C5 110.9(4) . . ?
C7 N1 C5 108.4(4) . . ?
N1 C1 C2 115.7(5) . . ?
N1 C1 H1A 108.4 . . ?
C2 C1 H1A 108.4 . . ?
N1 C1 H1B 108.4 . . ?
C2 C1 H1B 108.4 . . ?
H1A C1 H1B 107.4 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 115.0(5) . . ?
N1 C3 H3A 108.5 . . ?
C4 C3 H3A 108.5 . . ?
N1 C3 H3B 108.5 . . ?
C4 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 C6 114.1(4) . . ?
N1 C5 H5A 108.7 . . ?
C6 C5 H5A 108.7 . . ?
N1 C5 H5B 108.7 . . ?
C6 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 N1 115.1(5) . . ?
C8 C7 H7A 108.5 . . ?
N1 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
N1 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
C3 N1 C1 C2 60.4(6) . . . . ?
C7 N1 C1 C2 -59.4(6) . . . . ?
C5 N1 C1 C2 -178.7(5) . . . . ?
C1 N1 C3 C4 171.7(5) . . . . ?
C7 N1 C3 C4 -66.7(6) . . . . ?
C5 N1 C3 C4 52.3(7) . . . . ?
C1 N1 C5 C6 -66.2(6) . . . . ?
C3 N1 C5 C6 53.5(6) . . . . ?
C7 N1 C5 C6 172.6(5) . . . . ?
C1 N1 C7 C8 -55.3(6) . . . . ?
C3 N1 C7 C8 -175.4(5) . . . . ?
C5 N1 C7 C8 64.0(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
C1 H1A Br3 0.99 2.98 3.839(6) 145.7 .
C1 H1B Br2 0.99 3.08 3.875(6) 137.9 2_545
C4 H4B Br1 0.98 3.08 3.956(7) 149.4 1_455
C5 H5B Br3 0.99 3.12 4.098(5) 169.3 2_545
C6 H6C Br2 0.98 2.91 3.793(6) 151.2 3
C7 H7A Br1 0.99 3.07 4.034(6) 165.0 4_566
C7 H7B Br3 0.99 2.93 3.845(6) 153.6 1_455
C8 H8A Br2 0.98 3.09 4.026(7) 159.7 2_545

_refine_diff_density_max         1.579
_refine_diff_density_min         -2.962
_refine_diff_density_rms         0.417

_shelxl_version_number           2014-1

