# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_compound-1
_database_code_depnum_ccdc_archive 'CCDC 1587233'
_audit_update_record             
;
2017-11-23 deposited with the CCDC.
2018-02-28 downloaded from the CCDC.
;
#=====================================================================  

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 Br4 N2 O4 Zn2'
_chemical_formula_sum            'C16 H16 Br4 N2 O4 Zn2'
_chemical_formula_weight         750.69

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'
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      triclinic
_space_group_IT_number           2
_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'
'-x, -y, -z'

_cell_length_a                   6.849(2)
_cell_length_b                   12.673(4)
_cell_length_c                   13.419(4)
_cell_angle_alpha                78.619(13)
_cell_angle_beta                 86.759(15)
_cell_angle_gamma                86.386(17)
_cell_volume                     1138.4(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2886
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.4

_exptl_crystal_description       Prism
_exptl_crystal_colour            'Light Yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.190
_exptl_crystal_F_000             716
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_absorpt_coefficient_mu    9.150
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.405
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Sphere (Rigaku CrystalClear)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            11754
_diffrn_reflns_av_unetI/netI     0.1284
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.100
_diffrn_reflns_theta_max         27.536
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             4972
_reflns_number_gt                2496
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.99

_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       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_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)+(0.1005P)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_number_reflns         4972
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1114
_refine_ls_R_factor_gt           0.0690
_refine_ls_wR_factor_ref         0.2067
_refine_ls_wR_factor_gt          0.1985
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.070
_refine_ls_shift/su_mean         0.005

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
Zn1 Zn 0.24106(13) 0.37707(6) 0.28174(7) 0.0375(2) Uani 1 1 d . . . . .
Br22 Br 0.20763(12) 0.07662(6) 0.11496(7) 0.0510(2) Uani 1 1 d . . . . .
Br21 Br 0.56085(12) -0.02629(6) 0.34374(7) 0.0505(2) Uani 1 1 d . . . . .
Zn2 Zn 0.32374(13) 0.10606(6) 0.27241(8) 0.0413(2) Uani 1 1 d . . . . .
Br12 Br 0.37510(13) 0.47671(7) 0.38949(7) 0.0544(2) Uani 1 1 d . . . . .
Br11 Br 0.04250(13) 0.46635(8) 0.15109(9) 0.0677(3) Uani 1 1 d . . . . .
O12 O 0.4266(8) 0.2551(3) 0.2471(4) 0.0463(15) Uani 1 1 d . . . . .
N1 N 0.6409(8) 0.2730(4) -0.0423(5) 0.0345(16) Uani 1 1 d . . . . .
C25 C 0.0412(11) 0.3379(5) -0.4073(6) 0.040(2) Uani 1 1 d . . . . .
H25A H 0.0317 0.3896 -0.4668 0.048 Uiso 1 1 calc R U . . .
C18 C 0.5541(10) 0.2995(6) 0.1761(6) 0.0362(19) Uani 1 1 d . . . . .
N2 N -0.0791(8) 0.2573(4) -0.3884(5) 0.0332(15) Uani 1 1 d . . . . .
O11 O 0.5406(8) 0.3950(4) 0.1429(5) 0.0505(17) Uani 1 1 d . . . . .
C21 C -0.0670(11) 0.1827(6) -0.3036(6) 0.040(2) Uani 1 1 d . . . . .
H21A H -0.1520 0.1268 -0.2924 0.048 Uiso 1 1 calc R U . . .
O22 O 0.0941(8) 0.1110(4) 0.3667(5) 0.0548(17) Uani 1 1 d . . . . .
C16 C 0.7911(10) 0.2732(6) 0.0338(6) 0.040(2) Uani 1 1 d . . . . .
H16A H 0.8285 0.3464 0.0307 0.048 Uiso 1 1 calc R U . . .
H16B H 0.9069 0.2305 0.0177 0.048 Uiso 1 1 calc R U . . .
O21 O 0.0598(9) 0.2828(4) 0.3800(5) 0.0573(18) Uani 1 1 d . . . . .
C15 C 0.5429(10) 0.3655(5) -0.0851(6) 0.0359(19) Uani 1 1 d . . . . .
H15A H 0.5724 0.4301 -0.0681 0.043 Uiso 1 1 calc R U . . .
C12 C 0.4513(12) 0.1754(6) -0.1323(7) 0.046(2) Uani 1 1 d . . . . .
H12A H 0.4196 0.1094 -0.1457 0.055 Uiso 1 1 calc R U . . .
C13 C 0.3525(11) 0.2699(5) -0.1782(6) 0.036(2) Uani 1 1 d . . . . .
C11 C 0.5965(12) 0.1802(6) -0.0668(6) 0.045(2) Uani 1 1 d . . . . .
H11A H 0.6661 0.1169 -0.0386 0.054 Uiso 1 1 calc R U . . .
C24 C 0.1806(11) 0.3448(5) -0.3383(6) 0.039(2) Uani 1 1 d . . . . .
H24A H 0.2637 0.4017 -0.3514 0.047 Uiso 1 1 calc R U . . .
C14 C 0.4009(11) 0.3656(6) -0.1532(7) 0.045(2) Uani 1 1 d . . . . .
H14A H 0.3369 0.4301 -0.1826 0.054 Uiso 1 1 calc R U . . .
C17 C 0.7108(11) 0.2267(6) 0.1415(6) 0.040(2) Uani 1 1 d . . . . .
H17A H 0.6589 0.1570 0.1423 0.048 Uiso 1 1 calc R U . . .
H17B H 0.8166 0.2160 0.1882 0.048 Uiso 1 1 calc R U . . .
C23 C 0.1972(11) 0.2670(5) -0.2494(6) 0.037(2) Uani 1 1 d . . . . .
C26 C -0.2254(11) 0.2474(6) -0.4650(6) 0.044(2) Uani 1 1 d . . . . .
H26A H -0.2435 0.3161 -0.5114 0.053 Uiso 1 1 calc R U . . .
H26B H -0.3505 0.2298 -0.4301 0.053 Uiso 1 1 calc R U . . .
C22 C 0.0652(11) 0.1857(6) -0.2330(7) 0.044(2) Uani 1 1 d . . . . .
H22A H 0.0678 0.1334 -0.1737 0.053 Uiso 1 1 calc R U . . .
C27 C -0.1587(11) 0.1613(6) -0.5251(6) 0.044(2) Uani 1 1 d . . . . .
H27A H -0.1263 0.0952 -0.4774 0.053 Uiso 1 1 calc R U . . .
H27B H -0.2676 0.1477 -0.5631 0.053 Uiso 1 1 calc R U . . .
C28 C 0.0154(11) 0.1871(6) -0.5986(6) 0.040(2) 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
Zn1 O21 2.021(5) . ?
Zn1 O12 2.047(5) . ?
Zn1 Br11 2.3444(14) . ?
Zn1 Br12 2.3547(13) . ?
Br22 Zn2 2.4029(15) . ?
Br21 Zn2 2.3592(13) . ?
Zn2 O22 1.967(6) . ?
Zn2 O12 2.016(5) . ?
O12 C18 1.320(9) . ?
N1 C11 1.339(9) . ?
N1 C15 1.354(8) . ?
N1 C16 1.491(10) . ?
C25 N2 1.329(9) . ?
C25 C24 1.386(11) . ?
C25 H25A 0.9300 . ?
C18 O11 1.204(8) . ?
C18 C17 1.486(10) . ?
N2 C21 1.331(9) . ?
N2 C26 1.503(10) . ?
C21 C22 1.354(11) . ?
C21 H21A 0.9300 . ?
O22 C28 1.233(9) 1_556 ?
C16 C17 1.534(11) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
O21 C28 1.243(9) 1_556 ?
C15 C14 1.371(11) . ?
C15 H15A 0.9300 . ?
C12 C11 1.376(12) . ?
C12 C13 1.387(10) . ?
C12 H12A 0.9300 . ?
C13 C14 1.385(10) . ?
C13 C23 1.477(11) . ?
C11 H11A 0.9300 . ?
C24 C23 1.394(10) . ?
C24 H24A 0.9300 . ?
C14 H14A 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C23 C22 1.390(10) . ?
C26 C27 1.514(11) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C22 H22A 0.9300 . ?
C27 C28 1.514(11) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 O22 1.233(9) 1_554 ?
C28 O21 1.243(9) 1_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
O21 Zn1 O12 96.7(2) . . ?
O21 Zn1 Br11 105.06(18) . . ?
O12 Zn1 Br11 115.94(17) . . ?
O21 Zn1 Br12 101.59(19) . . ?
O12 Zn1 Br12 113.51(16) . . ?
Br11 Zn1 Br12 119.44(5) . . ?
O22 Zn2 O12 105.4(2) . . ?
O22 Zn2 Br21 110.85(17) . . ?
O12 Zn2 Br21 111.62(16) . . ?
O22 Zn2 Br22 107.22(19) . . ?
O12 Zn2 Br22 107.91(17) . . ?
Br21 Zn2 Br22 113.39(5) . . ?
C18 O12 Zn2 129.2(5) . . ?
C18 O12 Zn1 107.0(4) . . ?
Zn2 O12 Zn1 117.3(3) . . ?
C11 N1 C15 119.0(7) . . ?
C11 N1 C16 120.1(6) . . ?
C15 N1 C16 120.8(6) . . ?
N2 C25 C24 119.9(7) . . ?
N2 C25 H25A 120.0 . . ?
C24 C25 H25A 120.0 . . ?
O11 C18 O12 120.0(7) . . ?
O11 C18 C17 123.1(7) . . ?
O12 C18 C17 116.9(6) . . ?
C25 N2 C21 120.6(6) . . ?
C25 N2 C26 119.9(6) . . ?
C21 N2 C26 119.4(6) . . ?
N2 C21 C22 122.1(7) . . ?
N2 C21 H21A 118.9 . . ?
C22 C21 H21A 118.9 . . ?
C28 O22 Zn2 130.2(5) 1_556 . ?
N1 C16 C17 110.6(6) . . ?
N1 C16 H16A 109.5 . . ?
C17 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C28 O21 Zn1 139.0(6) 1_556 . ?
N1 C15 C14 121.2(7) . . ?
N1 C15 H15A 119.4 . . ?
C14 C15 H15A 119.4 . . ?
C11 C12 C13 119.4(7) . . ?
C11 C12 H12A 120.3 . . ?
C13 C12 H12A 120.3 . . ?
C12 C13 C14 118.0(7) . . ?
C12 C13 C23 120.5(7) . . ?
C14 C13 C23 121.5(6) . . ?
N1 C11 C12 122.1(7) . . ?
N1 C11 H11A 119.0 . . ?
C12 C11 H11A 119.0 . . ?
C25 C24 C23 120.4(7) . . ?
C25 C24 H24A 119.8 . . ?
C23 C24 H24A 119.8 . . ?
C15 C14 C13 120.2(7) . . ?
C15 C14 H14A 119.9 . . ?
C13 C14 H14A 119.9 . . ?
C18 C17 C16 111.4(6) . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C22 C23 C24 117.0(7) . . ?
C22 C23 C13 122.0(7) . . ?
C24 C23 C13 121.0(6) . . ?
N2 C26 C27 111.5(6) . . ?
N2 C26 H26A 109.3 . . ?
C27 C26 H26A 109.3 . . ?
N2 C26 H26B 109.3 . . ?
C27 C26 H26B 109.3 . . ?
H26A C26 H26B 108.0 . . ?
C21 C22 C23 119.9(7) . . ?
C21 C22 H22A 120.1 . . ?
C23 C22 H22A 120.1 . . ?
C28 C27 C26 115.6(6) . . ?
C28 C27 H27A 108.4 . . ?
C26 C27 H27A 108.4 . . ?
C28 C27 H27B 108.4 . . ?
C26 C27 H27B 108.4 . . ?
H27A C27 H27B 107.4 . . ?
O22 C28 O21 127.0(7) 1_554 1_554 ?
O22 C28 C27 116.1(6) 1_554 . ?
O21 C28 C27 116.8(7) 1_554 . ?

_refine_diff_density_max         2.054
_refine_diff_density_min         -1.190
_refine_diff_density_rms         0.326


_chemical_properties_physical    Light-sensitive,Photo-sensitive
_exptl_crystal_preparation       photochromism
