# Electronic Supplementary Material (ESI) for MedChemComm.
# 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_czf-zhr-c-zn02-140909
_audit_block_doi                 10.5517/cc14kp3h
_database_code_depnum_ccdc_archive 'CCDC 1059676'
_audit_update_record             
;
2015-04-15 deposited with the CCDC.
2015-11-12 downloaded from the CCDC.
;
_audit_creation_date             2014-10-17
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C10 H9 Br N O2 Zn0.5)'
_chemical_formula_sum            'C20 H18 Br2 N2 O4 Zn'
_chemical_formula_weight         575.55
_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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   5.06412(19)
_cell_length_b                   18.1609(12)
_cell_length_c                   11.4569(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.646(4)
_cell_angle_gamma                90.00
_cell_volume                     1044.31(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1292
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6127
_cell_measurement_theta_min      3.3586
_exptl_absorpt_coefficient_mu    5.031
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.830
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5059
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.59
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9784
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -84.00  -56.00   0.5000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.6216 -178.0000  120.0000 56

#__ type_ start__ end____ width___ exp.time_
  2 omega  -88.00  -43.00   0.5000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.6216  -77.0000   30.0000 90

#__ type_ start__ end____ width___ exp.time_
  3 omega  -74.00  -46.00   0.5000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.6216 -178.0000 -120.0000 56

#__ type_ start__ end____ width___ exp.time_
  4 omega  -13.00   58.00   0.5000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7935  -99.0000 -150.0000 142

#__ type_ start__ end____ width___ exp.time_
  5 omega  -50.00   40.00   0.5000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7935  -57.0000   60.0000 180
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0030927000
_diffrn_orient_matrix_UB_12      0.0378914000
_diffrn_orient_matrix_UB_13      0.0149062000
_diffrn_orient_matrix_UB_21      0.1080193000
_diffrn_orient_matrix_UB_22      -0.0055213000
_diffrn_orient_matrix_UB_23      0.0452818000
_diffrn_orient_matrix_UB_31      0.0910395000
_diffrn_orient_matrix_UB_32      0.0077484000
_diffrn_orient_matrix_UB_33      -0.0403476000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1540
_reflns_number_total             2139
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.115
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2139
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0585
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0692P)²+0.1188P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1466
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Br1 Br 0.96770(18) 0.31929(5) 0.45154(6) 0.0850(3) Uani 1 1 d . . .
Zn1 Zn 1.0000 0.5000 1.0000 0.0403(3) Uani 1 2 d S . .
O1 O 1.2315(6) 0.5203(2) 0.8700(3) 0.0411(9) Uani 1 1 d . . .
O2 O 0.7030(6) 0.5772(2) 0.9139(3) 0.0502(10) Uani 1 1 d D . .
H2 H 0.552(6) 0.558(2) 0.893(4) 0.075 Uiso 1 1 d D . .
N1 N 0.8572(7) 0.4164(2) 0.8777(4) 0.0388(10) Uani 1 1 d . . .
C1 C 1.1728(9) 0.4790(3) 0.7772(4) 0.0394(12) Uani 1 1 d . . .
C2 C 1.2893(10) 0.4855(3) 0.6750(4) 0.0475(14) Uani 1 1 d . . .
H2A H 1.4155 0.5222 0.6699 0.057 Uiso 1 1 calc R . .
C3 C 1.2219(11) 0.4386(4) 0.5800(5) 0.0572(16) Uani 1 1 d . . .
H3 H 1.3024 0.4452 0.5124 0.069 Uiso 1 1 calc R . .
C4 C 1.0425(11) 0.3835(3) 0.5828(5) 0.0523(14) Uani 1 1 d . . .
C5 C 0.9119(9) 0.3731(3) 0.6822(4) 0.0416(12) Uani 1 1 d . . .
C6 C 0.7150(11) 0.3189(3) 0.6948(5) 0.0524(15) Uani 1 1 d . . .
H6 H 0.6654 0.2857 0.6340 0.063 Uiso 1 1 calc R . .
C7 C 0.5992(11) 0.3151(3) 0.7941(5) 0.0507(14) Uani 1 1 d . . .
H7 H 0.4710 0.2794 0.8024 0.061 Uiso 1 1 calc R . .
C8 C 0.6749(10) 0.3652(3) 0.8838(5) 0.0464(13) Uani 1 1 d . . .
H8 H 0.5929 0.3626 0.9517 0.056 Uiso 1 1 calc R . .
C9 C 0.9764(8) 0.4212(3) 0.7788(4) 0.0378(12) Uani 1 1 d . . .
C10 C 0.7484(12) 0.6349(4) 0.8395(6) 0.0695(19) Uani 1 1 d D . .
H10A H 0.7710 0.6799 0.8839 0.104 Uiso 1 1 calc R . .
H10B H 0.5991 0.6397 0.7788 0.104 Uiso 1 1 calc R . .
H10C H 0.9065 0.6251 0.8042 0.104 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.1232(7) 0.0789(6) 0.0532(4) -0.0216(4) 0.0128(4) -0.0179(5)
Zn1 0.0312(4) 0.0453(5) 0.0446(5) -0.0072(4) 0.0057(3) -0.0062(4)
O1 0.0283(17) 0.052(2) 0.0436(19) -0.0072(17) 0.0069(15) -0.0081(15)
O2 0.0290(18) 0.052(3) 0.069(2) 0.0121(19) 0.0027(17) -0.0047(17)
N1 0.029(2) 0.043(3) 0.043(2) -0.006(2) 0.0015(17) -0.0012(18)
C1 0.029(2) 0.043(3) 0.045(3) 0.000(2) 0.000(2) 0.003(2)
C2 0.045(3) 0.050(4) 0.048(3) 0.001(3) 0.009(2) -0.007(2)
C3 0.062(4) 0.064(4) 0.047(3) -0.001(3) 0.013(3) 0.001(3)
C4 0.058(3) 0.052(4) 0.044(3) -0.009(3) -0.005(3) 0.000(3)
C5 0.036(3) 0.042(3) 0.044(3) -0.006(2) -0.004(2) 0.003(2)
C6 0.051(3) 0.044(3) 0.058(4) -0.010(3) -0.007(3) -0.004(3)
C7 0.043(3) 0.041(3) 0.067(4) 0.000(3) 0.002(3) -0.009(3)
C8 0.039(3) 0.046(3) 0.055(3) 0.000(3) 0.009(2) -0.006(2)
C9 0.026(2) 0.041(3) 0.045(3) 0.003(2) -0.003(2) 0.005(2)
C10 0.054(4) 0.064(5) 0.090(5) 0.019(4) 0.009(3) -0.006(3)

_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 C4 1.900(6) . ?
Zn1 O1 2.048(3) . ?
Zn1 O1 2.048(3) 3_767 ?
Zn1 O2 2.193(3) 3_767 ?
Zn1 O2 2.193(3) . ?
Zn1 N1 2.126(4) 3_767 ?
Zn1 N1 2.126(4) . ?
O1 C1 1.303(6) . ?
O2 H2 0.848(10) . ?
O2 C10 1.389(7) . ?
N1 C8 1.319(6) . ?
N1 C9 1.356(6) . ?
C1 C2 1.384(7) . ?
C1 C9 1.448(7) . ?
C2 H2A 0.9300 . ?
C2 C3 1.389(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.355(8) . ?
C4 C5 1.404(7) . ?
C5 C6 1.422(8) . ?
C5 C9 1.414(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.349(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.388(8) . ?
C8 H8 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
O1 Zn1 O1 180.000(1) 3_767 . ?
O1 Zn1 O2 88.99(14) 3_767 3_767 ?
O1 Zn1 O2 88.99(14) . . ?
O1 Zn1 O2 91.01(14) . 3_767 ?
O1 Zn1 O2 91.01(14) 3_767 . ?
O1 Zn1 N1 99.98(14) 3_767 . ?
O1 Zn1 N1 80.02(14) . . ?
O1 Zn1 N1 80.02(14) 3_767 3_767 ?
O1 Zn1 N1 99.98(14) . 3_767 ?
O2 Zn1 O2 180.000(1) 3_767 . ?
N1 Zn1 O2 89.56(15) 3_767 . ?
N1 Zn1 O2 90.44(15) . . ?
N1 Zn1 O2 89.56(15) . 3_767 ?
N1 Zn1 O2 90.44(15) 3_767 3_767 ?
N1 Zn1 N1 180.000(2) . 3_767 ?
C1 O1 Zn1 113.5(3) . . ?
Zn1 O2 H2 114(3) . . ?
C10 O2 Zn1 126.8(3) . . ?
C10 O2 H2 111(2) . . ?
C8 N1 Zn1 130.4(4) . . ?
C8 N1 C9 118.8(4) . . ?
C9 N1 Zn1 110.8(3) . . ?
O1 C1 C2 124.4(5) . . ?
O1 C1 C9 119.3(5) . . ?
C2 C1 C9 116.3(5) . . ?
C1 C2 H2A 119.2 . . ?
C1 C2 C3 121.5(5) . . ?
C3 C2 H2A 119.2 . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 122.0(5) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 Br1 119.9(5) . . ?
C3 C4 C5 120.5(5) . . ?
C5 C4 Br1 119.6(4) . . ?
C4 C5 C6 126.1(5) . . ?
C4 C5 C9 117.9(5) . . ?
C9 C5 C6 116.1(5) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.7(5) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 120.6 . . ?
C6 C7 C8 118.8(5) . . ?
C8 C7 H7 120.6 . . ?
N1 C8 C7 123.3(5) . . ?
N1 C8 H8 118.3 . . ?
C7 C8 H8 118.3 . . ?
N1 C9 C1 116.1(4) . . ?
N1 C9 C5 122.2(5) . . ?
C5 C9 C1 121.7(5) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
Br1 C4 C5 C6 -2.2(8) . . . . ?
Br1 C4 C5 C9 178.9(4) . . . . ?
Zn1 O1 C1 C2 175.7(4) . . . . ?
Zn1 O1 C1 C9 -5.3(6) . . . . ?
Zn1 N1 C8 C7 178.5(4) . . . . ?
Zn1 N1 C9 C1 1.1(5) . . . . ?
Zn1 N1 C9 C5 -178.4(4) . . . . ?
O1 Zn1 O1 C1 -136(100) 3_767 . . . ?
O1 Zn1 O2 C10 155.6(5) 3_767 . . . ?
O1 Zn1 O2 C10 -24.4(5) . . . . ?
O1 Zn1 N1 C8 179.1(5) . . . . ?
O1 Zn1 N1 C8 -0.9(5) 3_767 . . . ?
O1 Zn1 N1 C9 177.1(3) 3_767 . . . ?
O1 Zn1 N1 C9 -2.9(3) . . . . ?
O1 C1 C2 C3 178.5(5) . . . . ?
O1 C1 C9 N1 2.8(7) . . . . ?
O1 C1 C9 C5 -177.7(4) . . . . ?
O2 Zn1 O1 C1 93.8(3) 3_767 . . . ?
O2 Zn1 O1 C1 -86.2(3) . . . . ?
O2 Zn1 O2 C10 44(100) 3_767 . . . ?
O2 Zn1 N1 C8 88.0(5) 3_767 . . . ?
O2 Zn1 N1 C8 -92.0(5) . . . . ?
O2 Zn1 N1 C9 86.0(3) . . . . ?
O2 Zn1 N1 C9 -94.0(3) 3_767 . . . ?
N1 Zn1 O1 C1 -175.6(3) 3_767 . . . ?
N1 Zn1 O1 C1 4.4(3) . . . . ?
N1 Zn1 O2 C10 -104.4(5) . . . . ?
N1 Zn1 O2 C10 75.6(5) 3_767 . . . ?
N1 Zn1 N1 C8 -133(100) 3_767 . . . ?
N1 Zn1 N1 C9 45(100) 3_767 . . . ?
C1 C2 C3 C4 -1.0(9) . . . . ?
C2 C1 C9 N1 -178.1(4) . . . . ?
C2 C1 C9 C5 1.3(7) . . . . ?
C2 C3 C4 Br1 -178.0(4) . . . . ?
C2 C3 C4 C5 1.7(9) . . . . ?
C3 C4 C5 C6 178.1(6) . . . . ?
C3 C4 C5 C9 -0.8(8) . . . . ?
C4 C5 C6 C7 -178.7(5) . . . . ?
C4 C5 C9 N1 178.7(4) . . . . ?
C4 C5 C9 C1 -0.7(7) . . . . ?
C5 C6 C7 C8 0.3(8) . . . . ?
C6 C5 C9 N1 -0.3(7) . . . . ?
C6 C5 C9 C1 -179.7(5) . . . . ?
C6 C7 C8 N1 -0.7(9) . . . . ?
C8 N1 C9 C1 179.4(4) . . . . ?
C8 N1 C9 C5 -0.1(7) . . . . ?
C9 N1 C8 C7 0.6(8) . . . . ?
C9 C1 C2 C3 -0.5(8) . . . . ?
C9 C5 C6 C7 0.2(8) . . . . ?

