# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_e1312a
_database_code_depnum_ccdc_archive 'CCDC 1497261'
_audit_update_record             
;
2016-08-02 deposited with the CCDC.
2017-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H30 I N3 O Zn'
_chemical_formula_sum            'C27 H30 I N3 O Zn'
_chemical_formula_weight         604.81

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'
I I -0.4742 1.8119 '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                   13.7585(6)
_cell_length_b                   12.5082(4)
_cell_length_c                   15.7328(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.107(4)
_cell_angle_gamma                90
_cell_volume                     2542.49(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7880
_cell_measurement_theta_min      2.1277
_cell_measurement_theta_max      28.4823

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.599
_exptl_crystal_size_mid          0.229
_exptl_crystal_size_min          0.062
_exptl_absorpt_coefficient_mu    2.204
_shelx_estimated_absorpt_T_min   0.352
_shelx_estimated_absorpt_T_max   0.876
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.492954
_exptl_absorpt_correction_T_max  0.869034
_exptl_absorpt_process_details   'Oxford Diffraction CrysAlis'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Oxford Sapphire CCD'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean 8.2564
_diffrn_reflns_number            17638
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.266
_diffrn_reflns_theta_max         28.560
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5858
_reflns_number_gt                4177
_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       'Oxford Diffraction CrysAlis'
_computing_cell_refinement       'Oxford Diffraction CrysAlis'
_computing_data_reduction        'Oxford Diffraction CrysAlis'
_computing_structure_solution    'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'

_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)+(0.0309P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5858
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0601
_refine_ls_wR_factor_gt          0.0569
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_restrained_S_all      0.918
_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
Zn1 Zn 0.07508(2) 0.25681(2) 0.09762(2) 0.02983(7) Uani 1 1 d . . . . .
I1 I 0.08278(2) 0.15761(2) 0.24332(2) 0.05019(7) Uani 1 1 d . . . . .
O1 O 0.21004(12) 0.28184(13) 0.08467(11) 0.0360(4) Uani 1 1 d . . . . .
C1 C 0.22494(16) 0.22938(17) 0.01756(15) 0.0263(5) Uani 1 1 d . . . . .
C2 C 0.31821(16) 0.24140(17) -0.00233(15) 0.0283(5) Uani 1 1 d . . . . .
C3 C 0.32875(17) 0.18187(18) -0.07161(15) 0.0335(6) Uani 1 1 d . . . . .
H3A H 0.3898 0.1893 -0.0839 0.040 Uiso 1 1 calc R U . . .
C4 C 0.25388(17) 0.11010(19) -0.12570(15) 0.0311(5) Uani 1 1 d . . . . .
C5 C 0.16279(17) 0.10255(18) -0.10806(15) 0.0295(5) Uani 1 1 d . . . . .
H5A H 0.1107 0.0573 -0.1430 0.035 Uiso 1 1 calc R U . . .
C6 C 0.14739(16) 0.16155(17) -0.03890(14) 0.0255(5) Uani 1 1 d . . . . .
N1 N 0.05403(13) 0.16386(14) -0.01977(12) 0.0267(4) Uani 1 1 d . . . . .
C7 C -0.02763(17) 0.11183(18) -0.06553(16) 0.0316(5) Uani 1 1 d . . . . .
H7A H -0.0218 0.0648 -0.1093 0.038 Uiso 1 1 calc R U . . .
C8 C -0.12870(16) 0.11989(18) -0.05506(15) 0.0270(5) Uani 1 1 d . . . . .
C9 C -0.20209(17) 0.04277(19) -0.09947(16) 0.0361(6) Uani 1 1 d . . . . .
H9A H -0.1841 -0.0098 -0.1332 0.043 Uiso 1 1 calc R U . . .
C10 C -0.29972(18) 0.0423(2) -0.09486(17) 0.0420(6) Uani 1 1 d . . . . .
H10A H -0.3467 -0.0105 -0.1246 0.050 Uiso 1 1 calc R U . . .
C11 C -0.32778(19) 0.1197(2) -0.04650(18) 0.0460(7) Uani 1 1 d . . . . .
H11A H -0.3936 0.1185 -0.0423 0.055 Uiso 1 1 calc R U . . .
C12 C -0.25932(18) 0.1992(2) -0.00403(17) 0.0406(6) Uani 1 1 d . . . . .
H12A H -0.2796 0.2524 0.0277 0.049 Uiso 1 1 calc R U . . .
C13 C -0.16054(16) 0.20084(19) -0.00819(15) 0.0299(5) Uani 1 1 d . . . . .
N2 N -0.08960(14) 0.28283(15) 0.03508(12) 0.0294(4) Uani 1 1 d . . . . .
C14 C -0.11855(18) 0.37791(19) 0.04042(15) 0.0313(5) Uani 1 1 d . . . . .
H14A H -0.1877 0.3969 0.0135 0.038 Uiso 1 1 calc R U . . .
C15 C -0.04168(17) 0.45758(18) 0.08948(14) 0.0289(5) Uani 1 1 d . . . . .
C16 C -0.06702(19) 0.56102(19) 0.10396(16) 0.0366(6) Uani 1 1 d . . . . .
H16A H -0.1352 0.5846 0.0810 0.044 Uiso 1 1 calc R U . . .
C17 C 0.0108(2) 0.62836(19) 0.15311(17) 0.0414(6) Uani 1 1 d . . . . .
H17A H -0.0047 0.6977 0.1657 0.050 Uiso 1 1 calc R U . . .
C18 C 0.1108(2) 0.5935(2) 0.18354(17) 0.0436(6) Uani 1 1 d . . . . .
H18A H 0.1643 0.6387 0.2160 0.052 Uiso 1 1 calc R U . . .
C19 C 0.13082(19) 0.4897(2) 0.16502(16) 0.0388(6) Uani 1 1 d . . . . .
H19A H 0.1991 0.4662 0.1846 0.047 Uiso 1 1 calc R U . . .
N3 N 0.05640(14) 0.42188(15) 0.12023(12) 0.0310(4) Uani 1 1 d . . . . .
C20 C 0.40287(17) 0.31919(18) 0.05380(16) 0.0326(5) Uani 1 1 d . . . . .
C21 C 0.4961(2) 0.3208(2) 0.0224(2) 0.0524(7) Uani 1 1 d . . . . .
H21A H 0.4743 0.3420 -0.0400 0.063 Uiso 1 1 calc R U . . .
H21B H 0.5465 0.3707 0.0585 0.063 Uiso 1 1 calc R U . . .
H21C H 0.5262 0.2507 0.0290 0.063 Uiso 1 1 calc R U . . .
C22 C 0.35975(19) 0.43281(19) 0.04480(19) 0.0453(6) Uani 1 1 d . . . . .
H22A H 0.3007 0.4344 0.0641 0.054 Uiso 1 1 calc R U . . .
H22B H 0.4120 0.4803 0.0819 0.054 Uiso 1 1 calc R U . . .
H22C H 0.3394 0.4552 -0.0173 0.054 Uiso 1 1 calc R U . . .
C23 C 0.4408(2) 0.2852(2) 0.15311(18) 0.0483(7) Uani 1 1 d . . . . .
H23A H 0.3834 0.2835 0.1746 0.058 Uiso 1 1 calc R U . . .
H23B H 0.4713 0.2153 0.1588 0.058 Uiso 1 1 calc R U . . .
H23C H 0.4915 0.3353 0.1883 0.058 Uiso 1 1 calc R U . . .
C24 C 0.27510(18) 0.0498(2) -0.20248(16) 0.0385(6) Uani 1 1 d . . . . .
C25 C 0.2787(3) 0.1295(2) -0.27452(19) 0.0639(9) Uani 1 1 d . . . . .
H25A H 0.3314 0.1819 -0.2478 0.077 Uiso 1 1 calc R U . . .
H25B H 0.2942 0.0925 -0.3218 0.077 Uiso 1 1 calc R U . . .
H25C H 0.2128 0.1644 -0.2994 0.077 Uiso 1 1 calc R U . . .
C26 C 0.1909(2) -0.0316(2) -0.2474(2) 0.0648(9) Uani 1 1 d . . . . .
H26A H 0.1871 -0.0828 -0.2032 0.078 Uiso 1 1 calc R U . . .
H26B H 0.1256 0.0043 -0.2724 0.078 Uiso 1 1 calc R U . . .
H26C H 0.2070 -0.0676 -0.2948 0.078 Uiso 1 1 calc R U . . .
C27 C 0.3779(2) -0.0098(3) -0.1661(2) 0.0725(10) Uani 1 1 d . . . . .
H27A H 0.4324 0.0399 -0.1373 0.087 Uiso 1 1 calc R U . . .
H27B H 0.3742 -0.0624 -0.1228 0.087 Uiso 1 1 calc R U . . .
H27C H 0.3917 -0.0445 -0.2152 0.087 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
Zn1 O1 1.9616(14) . ?
Zn1 N1 2.1164(18) . ?
Zn1 N3 2.1257(19) . ?
Zn1 N2 2.1621(18) . ?
Zn1 I1 2.5765(3) . ?
O1 C1 1.318(2) . ?
C1 C6 1.413(3) . ?
C1 C2 1.430(3) . ?
C2 C3 1.368(3) . ?
C2 C20 1.541(3) . ?
C3 C4 1.410(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.377(3) . ?
C4 C24 1.535(3) . ?
C5 C6 1.390(3) . ?
C5 H5A 0.9300 . ?
C6 N1 1.417(3) . ?
N1 C7 1.284(3) . ?
C7 C8 1.459(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.398(3) . ?
C8 C13 1.408(3) . ?
C9 C10 1.370(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.366(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.375(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.383(3) . ?
C12 H12A 0.9300 . ?
C13 N2 1.418(3) . ?
N2 C14 1.266(3) . ?
C14 C15 1.465(3) . ?
C14 H14A 0.9300 . ?
C15 N3 1.344(3) . ?
C15 C16 1.379(3) . ?
C16 C17 1.373(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.364(3) . ?
C17 H17A 0.9300 . ?
C18 C19 1.379(3) . ?
C18 H18A 0.9300 . ?
C19 N3 1.330(3) . ?
C19 H19A 0.9300 . ?
C20 C21 1.525(3) . ?
C20 C23 1.528(3) . ?
C20 C22 1.528(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C26 1.521(4) . ?
C24 C25 1.523(4) . ?
C24 C27 1.526(3) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
O1 Zn1 N1 81.22(6) . . ?
O1 Zn1 N3 92.04(7) . . ?
N1 Zn1 N3 133.75(7) . . ?
O1 Zn1 N2 144.10(7) . . ?
N1 Zn1 N2 82.99(7) . . ?
N3 Zn1 N2 76.22(7) . . ?
O1 Zn1 I1 114.73(5) . . ?
N1 Zn1 I1 117.60(5) . . ?
N3 Zn1 I1 106.81(5) . . ?
N2 Zn1 I1 101.16(5) . . ?
C1 O1 Zn1 114.66(13) . . ?
O1 C1 C6 120.73(18) . . ?
O1 C1 C2 121.4(2) . . ?
C6 C1 C2 117.80(19) . . ?
C3 C2 C1 117.8(2) . . ?
C3 C2 C20 122.26(19) . . ?
C1 C2 C20 119.96(19) . . ?
C2 C3 C4 124.87(19) . . ?
C2 C3 H3A 117.6 . . ?
C4 C3 H3A 117.6 . . ?
C5 C4 C3 116.7(2) . . ?
C5 C4 C24 123.9(2) . . ?
C3 C4 C24 119.38(19) . . ?
C4 C5 C6 121.0(2) . . ?
C4 C5 H5A 119.5 . . ?
C6 C5 H5A 119.5 . . ?
C5 C6 C1 121.71(19) . . ?
C5 C6 N1 124.8(2) . . ?
C1 C6 N1 113.47(18) . . ?
C7 N1 C6 123.59(19) . . ?
C7 N1 Zn1 126.77(14) . . ?
C6 N1 Zn1 109.55(13) . . ?
N1 C7 C8 125.9(2) . . ?
N1 C7 H7A 117.1 . . ?
C8 C7 H7A 117.1 . . ?
C9 C8 C13 117.18(19) . . ?
C9 C8 C7 116.7(2) . . ?
C13 C8 C7 126.1(2) . . ?
C10 C9 C8 122.0(2) . . ?
C10 C9 H9A 119.0 . . ?
C8 C9 H9A 119.0 . . ?
C11 C10 C9 119.8(2) . . ?
C11 C10 H10A 120.1 . . ?
C9 C10 H10A 120.1 . . ?
C10 C11 C12 120.4(2) . . ?
C10 C11 H11A 119.8 . . ?
C12 C11 H11A 119.8 . . ?
C11 C12 C13 120.5(2) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C12 C13 C8 120.1(2) . . ?
C12 C13 N2 120.9(2) . . ?
C8 C13 N2 118.99(18) . . ?
C14 N2 C13 122.06(19) . . ?
C14 N2 Zn1 114.55(16) . . ?
C13 N2 Zn1 123.38(14) . . ?
N2 C14 C15 119.2(2) . . ?
N2 C14 H14A 120.4 . . ?
C15 C14 H14A 120.4 . . ?
N3 C15 C16 122.1(2) . . ?
N3 C15 C14 114.7(2) . . ?
C16 C15 C14 123.2(2) . . ?
C17 C16 C15 118.4(2) . . ?
C17 C16 H16A 120.8 . . ?
C15 C16 H16A 120.8 . . ?
C18 C17 C16 119.9(2) . . ?
C18 C17 H17A 120.0 . . ?
C16 C17 H17A 120.0 . . ?
C17 C18 C19 118.5(2) . . ?
C17 C18 H18A 120.7 . . ?
C19 C18 H18A 120.7 . . ?
N3 C19 C18 122.6(2) . . ?
N3 C19 H19A 118.7 . . ?
C18 C19 H19A 118.7 . . ?
C19 N3 C15 118.3(2) . . ?
C19 N3 Zn1 126.36(16) . . ?
C15 N3 Zn1 115.26(15) . . ?
C21 C20 C23 107.8(2) . . ?
C21 C20 C22 107.51(19) . . ?
C23 C20 C22 109.8(2) . . ?
C21 C20 C2 112.15(19) . . ?
C23 C20 C2 109.59(19) . . ?
C22 C20 C2 109.95(19) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C26 C24 C25 107.9(2) . . ?
C26 C24 C27 107.8(2) . . ?
C25 C24 C27 109.7(2) . . ?
C26 C24 C4 111.95(19) . . ?
C25 C24 C4 109.1(2) . . ?
C27 C24 C4 110.3(2) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 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
Zn1 O1 C1 C6 0.1(3) . . . . ?
Zn1 O1 C1 C2 178.24(15) . . . . ?
O1 C1 C2 C3 178.3(2) . . . . ?
C6 C1 C2 C3 -3.6(3) . . . . ?
O1 C1 C2 C20 -1.5(3) . . . . ?
C6 C1 C2 C20 176.63(19) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C20 C2 C3 C4 -179.5(2) . . . . ?
C2 C3 C4 C5 1.8(4) . . . . ?
C2 C3 C4 C24 178.9(2) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C24 C4 C5 C6 -178.3(2) . . . . ?
C4 C5 C6 C1 -1.6(3) . . . . ?
C4 C5 C6 N1 175.8(2) . . . . ?
O1 C1 C6 C5 -177.7(2) . . . . ?
C2 C1 C6 C5 4.1(3) . . . . ?
O1 C1 C6 N1 4.6(3) . . . . ?
C2 C1 C6 N1 -173.60(18) . . . . ?
C5 C6 N1 C7 -0.7(3) . . . . ?
C1 C6 N1 C7 176.9(2) . . . . ?
C5 C6 N1 Zn1 175.93(18) . . . . ?
C1 C6 N1 Zn1 -6.4(2) . . . . ?
C6 N1 C7 C8 -173.1(2) . . . . ?
Zn1 N1 C7 C8 10.8(3) . . . . ?
N1 C7 C8 C9 -168.6(2) . . . . ?
N1 C7 C8 C13 14.7(4) . . . . ?
C13 C8 C9 C10 -2.8(3) . . . . ?
C7 C8 C9 C10 -179.8(2) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?
C9 C10 C11 C12 1.4(4) . . . . ?
C10 C11 C12 C13 -1.3(4) . . . . ?
C11 C12 C13 C8 -0.9(4) . . . . ?
C11 C12 C13 N2 179.7(2) . . . . ?
C9 C8 C13 C12 2.8(3) . . . . ?
C7 C8 C13 C12 179.5(2) . . . . ?
C9 C8 C13 N2 -177.8(2) . . . . ?
C7 C8 C13 N2 -1.1(3) . . . . ?
C12 C13 N2 C14 -34.6(3) . . . . ?
C8 C13 N2 C14 146.0(2) . . . . ?
C12 C13 N2 Zn1 144.99(19) . . . . ?
C8 C13 N2 Zn1 -34.4(3) . . . . ?
C13 N2 C14 C15 177.39(19) . . . . ?
Zn1 N2 C14 C15 -2.2(3) . . . . ?
N2 C14 C15 N3 4.0(3) . . . . ?
N2 C14 C15 C16 -175.5(2) . . . . ?
N3 C15 C16 C17 -1.4(3) . . . . ?
C14 C15 C16 C17 178.1(2) . . . . ?
C15 C16 C17 C18 2.3(3) . . . . ?
C16 C17 C18 C19 -1.1(4) . . . . ?
C17 C18 C19 N3 -1.3(4) . . . . ?
C18 C19 N3 C15 2.2(3) . . . . ?
C18 C19 N3 Zn1 -174.11(18) . . . . ?
C16 C15 N3 C19 -0.8(3) . . . . ?
C14 C15 N3 C19 179.6(2) . . . . ?
C16 C15 N3 Zn1 175.89(16) . . . . ?
C14 C15 N3 Zn1 -3.7(2) . . . . ?
C3 C2 C20 C21 0.2(3) . . . . ?
C1 C2 C20 C21 180.0(2) . . . . ?
C3 C2 C20 C23 -119.5(2) . . . . ?
C1 C2 C20 C23 60.3(3) . . . . ?
C3 C2 C20 C22 119.7(2) . . . . ?
C1 C2 C20 C22 -60.5(3) . . . . ?
C5 C4 C24 C26 -8.7(3) . . . . ?
C3 C4 C24 C26 174.5(2) . . . . ?
C5 C4 C24 C25 110.7(3) . . . . ?
C3 C4 C24 C25 -66.2(3) . . . . ?
C5 C4 C24 C27 -128.8(3) . . . . ?
C3 C4 C24 C27 54.4(3) . . . . ?

_refine_diff_density_max         0.474
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.066

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_e709a
_database_code_depnum_ccdc_archive 'CCDC 1497259'
_audit_update_record             
;
2017-06-26 deposited with the CCDC.
2017-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H33 N3 O3 Zn, 0.5(H2 O)'
_chemical_formula_sum            'C29 H34 N3 O3.50 Zn'
_chemical_formula_weight         545.96

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'

_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                   10.1927(13)
_cell_length_b                   10.2059(12)
_cell_length_c                   14.7907(19)
_cell_angle_alpha                94.834(10)
_cell_angle_beta                 98.779(11)
_cell_angle_gamma                114.583(12)
_cell_volume                     1364.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3504
_cell_measurement_theta_min      2.2078
_cell_measurement_theta_max      27.8588

_exptl_crystal_description       Plate
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             574
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.168
_exptl_absorpt_coefficient_mu    0.937
_shelx_estimated_absorpt_T_min   0.637
_shelx_estimated_absorpt_T_max   0.859
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.708
_exptl_absorpt_correction_T_max  0.873
_exptl_absorpt_process_details   'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Oxford Sapphire CCD'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean 8.2564
_diffrn_reflns_number            8580
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.225
_diffrn_reflns_theta_max         27.921
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5709
_reflns_number_gt                4310
_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       'CrysAlisPro 1.171.38.43, Rigaku OD, 2015'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43, Rigaku OD, 2015'
_computing_data_reduction        'CrysAlisPro 1.171.38.43, Rigaku OD, 2015'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'

_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)+(0.1473P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     patterson
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5709
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_ref         0.2128
_refine_ls_wR_factor_gt          0.1653
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
Zn1 Zn 0.88881(5) 0.64538(5) 0.66132(3) 0.0366(2) Uani 1 1 d . . . . .
O1 O 0.8459(3) 0.6764(3) 0.78520(19) 0.0394(7) Uani 1 1 d . . . . .
C1 C 0.7975(4) 0.7761(4) 0.7963(3) 0.0319(8) Uani 1 1 d . . . . .
C2 C 0.7596(4) 0.8137(4) 0.8811(3) 0.0326(8) Uani 1 1 d . . . . .
C3 C 0.7104(5) 0.9215(4) 0.8872(3) 0.0367(9) Uani 1 1 d . . . . .
H3A H 0.6871 0.9455 0.9427 0.044 Uiso 1 1 calc R U . . .
C4 C 0.6940(5) 0.9959(5) 0.8145(3) 0.0388(9) Uani 1 1 d . . . . .
C5 C 0.7291(5) 0.9586(5) 0.7323(3) 0.0393(9) Uani 1 1 d . . . . .
H5A H 0.7193 1.0066 0.6828 0.047 Uiso 1 1 calc R U . . .
C6 C 0.7786(4) 0.8510(4) 0.7217(3) 0.0328(8) Uani 1 1 d . . . . .
N1 N 0.8222(4) 0.8101(3) 0.6411(2) 0.0323(7) Uani 1 1 d . . . . .
C7 C 0.8094(4) 0.8608(4) 0.5653(3) 0.0346(8) Uani 1 1 d . . . . .
H7A H 0.7664 0.9253 0.5643 0.042 Uiso 1 1 calc R U . . .
C8 C 0.8553(4) 0.8281(4) 0.4799(3) 0.0339(8) Uani 1 1 d . . . . .
C9 C 0.8069(5) 0.8761(5) 0.4018(3) 0.0434(10) Uani 1 1 d . . . . .
H9A H 0.7478 0.9245 0.4062 0.052 Uiso 1 1 calc R U . . .
C10 C 0.8449(5) 0.8533(5) 0.3173(3) 0.0497(11) Uani 1 1 d . . . . .
H10A H 0.8092 0.8847 0.2660 0.060 Uiso 1 1 calc R U . . .
C11 C 0.9337(5) 0.7854(6) 0.3089(3) 0.0499(11) Uani 1 1 d . . . . .
H11A H 0.9592 0.7715 0.2523 0.060 Uiso 1 1 calc R U . . .
C12 C 0.9860(5) 0.7369(5) 0.3852(3) 0.0442(10) Uani 1 1 d . . . . .
H12A H 1.0459 0.6897 0.3794 0.053 Uiso 1 1 calc R U . . .
C13 C 0.9493(4) 0.7586(4) 0.4703(3) 0.0357(8) Uani 1 1 d . . . . .
N2 N 1.0061(4) 0.7158(4) 0.5503(2) 0.0341(7) Uani 1 1 d . . . . .
C14 C 1.1284(5) 0.7121(5) 0.5611(3) 0.0417(9) Uani 1 1 d . . . . .
H14A H 1.1843 0.7349 0.5156 0.050 Uiso 1 1 calc R U . . .
C15 C 1.1825(5) 0.6712(4) 0.6463(3) 0.0388(9) Uani 1 1 d . . . . .
C16 C 1.3190(5) 0.6724(6) 0.6648(3) 0.0527(12) Uani 1 1 d . . . . .
H16A H 1.3792 0.6954 0.6216 0.063 Uiso 1 1 calc R U . . .
C17 C 1.3659(6) 0.6387(7) 0.7493(4) 0.0630(14) Uani 1 1 d . . . . .
H17A H 1.4572 0.6369 0.7633 0.076 Uiso 1 1 calc R U . . .
C18 C 1.2722(6) 0.6074(7) 0.8128(4) 0.0620(14) Uani 1 1 d . . . . .
H18A H 1.3012 0.5862 0.8703 0.074 Uiso 1 1 calc R U . . .
C19 C 1.1360(6) 0.6085(6) 0.7887(3) 0.0538(12) Uani 1 1 d . . . . .
H19A H 1.0732 0.5861 0.8304 0.065 Uiso 1 1 calc R U . . .
N3 N 1.0926(4) 0.6404(4) 0.7082(2) 0.0421(8) Uani 1 1 d . . . . .
C20 C 0.7714(5) 0.7319(5) 0.9630(3) 0.0412(9) Uani 1 1 d . . . . .
C21 C 0.6671(7) 0.5700(5) 0.9314(4) 0.0596(13) Uani 1 1 d . . . . .
H21A H 0.5680 0.5586 0.9129 0.071 Uiso 1 1 calc R U . . .
H21B H 0.6955 0.5323 0.8799 0.071 Uiso 1 1 calc R U . . .
H21C H 0.6725 0.5174 0.9816 0.071 Uiso 1 1 calc R U . . .
C22 C 0.7265(8) 0.7883(7) 1.0482(3) 0.0709(17) Uani 1 1 d . . . . .
H22A H 0.7910 0.8900 1.0690 0.085 Uiso 1 1 calc R U . . .
H22B H 0.6267 0.7755 1.0311 0.085 Uiso 1 1 calc R U . . .
H22C H 0.7341 0.7342 1.0972 0.085 Uiso 1 1 calc R U . . .
C23 C 0.9300(6) 0.7519(8) 0.9928(4) 0.0712(17) Uani 1 1 d . . . . .
H23A H 0.9946 0.8538 1.0125 0.085 Uiso 1 1 calc R U . . .
H23B H 0.9360 0.6997 1.0431 0.085 Uiso 1 1 calc R U . . .
H23C H 0.9590 0.7146 0.9414 0.085 Uiso 1 1 calc R U . . .
C24 C 0.6430(6) 1.1181(5) 0.8263(3) 0.0505(11) Uani 1 1 d . . . . .
C25 C 0.6498(8) 1.1706(7) 0.9263(4) 0.0758(18) Uani 1 1 d . . . . .
H25A H 0.7478 1.2011 0.9616 0.091 Uiso 1 1 calc R U . . .
H25B H 0.6247 1.2515 0.9296 0.091 Uiso 1 1 calc R U . . .
H25C H 0.5812 1.0927 0.9511 0.091 Uiso 1 1 calc R U . . .
C26 C 0.7505(9) 1.2550(7) 0.7909(5) 0.088(2) Uani 1 1 d . . . . .
H26A H 0.8485 1.2886 0.8269 0.105 Uiso 1 1 calc R U . . .
H26B H 0.7499 1.2290 0.7269 0.105 Uiso 1 1 calc R U . . .
H26C H 0.7191 1.3312 0.7971 0.105 Uiso 1 1 calc R U . . .
C27 C 0.4923(9) 1.0695(10) 0.7686(7) 0.126(4) Uani 1 1 d . . . . .
H27A H 0.4913 1.0368 0.7056 0.151 Uiso 1 1 calc R U . . .
H27B H 0.4225 0.9908 0.7923 0.151 Uiso 1 1 calc R U . . .
H27C H 0.4660 1.1496 0.7708 0.151 Uiso 1 1 calc R U . . .
O2 O 0.7554(4) 0.4460(3) 0.5919(2) 0.0556(9) Uani 1 1 d . . . . .
C28 C 0.6228(8) 0.3807(6) 0.5793(3) 0.0636(15) Uani 1 1 d . . . . .
C29 C 0.5385(7) 0.4550(7) 0.6214(5) 0.086(2) Uani 1 1 d . . . . .
H29A H 0.4349 0.3910 0.6059 0.104 Uiso 1 1 calc R U . . .
H29B H 0.5714 0.4769 0.6876 0.104 Uiso 1 1 calc R U . . .
H29C H 0.5562 0.5439 0.5973 0.104 Uiso 1 1 calc R U . . .
O3 O 0.5472(7) 0.2586(5) 0.5303(4) 0.1059(18) Uani 1 1 d . . . . .
O1W O 0.6129(11) 0.0448(10) 0.5065(8) 0.099(3) Uani 0.5 1 d . . P . .
H1W1 H 0.5634 -0.0478 0.4954 0.119 Uiso 0.5 1 d . U P . .
H2W1 H 0.5808 0.1073 0.5319 0.119 Uiso 0.5 1 d . U P . .


_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 O1 1.977(3) . ?
Zn1 O2 1.991(3) . ?
Zn1 N1 2.086(3) . ?
Zn1 N3 2.110(3) . ?
Zn1 N2 2.174(3) . ?
O1 C1 1.311(4) . ?
C1 C6 1.428(5) . ?
C1 C2 1.436(5) . ?
C2 C3 1.388(5) . ?
C2 C20 1.545(5) . ?
C3 C4 1.396(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.385(6) . ?
C4 C24 1.545(6) . ?
C5 C6 1.393(5) . ?
C5 H5A 0.9300 . ?
C6 N1 1.423(5) . ?
N1 C7 1.285(5) . ?
C7 C8 1.471(5) . ?
C7 H7A 0.9300 . ?
C8 C9 1.392(6) . ?
C8 C13 1.426(6) . ?
C9 C10 1.393(6) . ?
C9 H9A 0.9300 . ?
C10 C11 1.363(7) . ?
C10 H10A 0.9300 . ?
C11 C12 1.390(6) . ?
C11 H11A 0.9300 . ?
C12 C13 1.392(6) . ?
C12 H12A 0.9300 . ?
C13 N2 1.419(5) . ?
N2 C14 1.250(5) . ?
C14 C15 1.460(6) . ?
C14 H14A 0.9300 . ?
C15 N3 1.357(5) . ?
C15 C16 1.371(6) . ?
C16 C17 1.391(7) . ?
C16 H16A 0.9300 . ?
C17 C18 1.403(8) . ?
C17 H17A 0.9300 . ?
C18 C19 1.385(7) . ?
C18 H18A 0.9300 . ?
C19 N3 1.321(6) . ?
C19 H19A 0.9300 . ?
C20 C21 1.528(7) . ?
C20 C23 1.531(7) . ?
C20 C22 1.549(6) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C27 1.493(9) . ?
C24 C25 1.510(7) . ?
C24 C26 1.566(8) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
O2 C28 1.208(7) . ?
C28 O3 1.245(7) . ?
C28 C29 1.526(9) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
O1W H1W1 0.852(9) . ?
O1W H2W1 0.910(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
O1 Zn1 O2 111.90(13) . . ?
O1 Zn1 N1 81.72(11) . . ?
O2 Zn1 N1 117.07(14) . . ?
O1 Zn1 N3 96.64(13) . . ?
O2 Zn1 N3 105.44(15) . . ?
N1 Zn1 N3 134.85(14) . . ?
O1 Zn1 N2 153.34(13) . . ?
O2 Zn1 N2 94.73(13) . . ?
N1 Zn1 N2 85.06(12) . . ?
N3 Zn1 N2 76.67(13) . . ?
C1 O1 Zn1 114.5(2) . . ?
O1 C1 C6 120.0(3) . . ?
O1 C1 C2 122.8(3) . . ?
C6 C1 C2 117.1(3) . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 C20 121.3(3) . . ?
C1 C2 C20 119.6(3) . . ?
C2 C3 C4 123.6(4) . . ?
C2 C3 H3A 118.2 . . ?
C4 C3 H3A 118.2 . . ?
C5 C4 C3 117.4(4) . . ?
C5 C4 C24 121.4(4) . . ?
C3 C4 C24 121.2(4) . . ?
C4 C5 C6 121.8(4) . . ?
C4 C5 H5A 119.1 . . ?
C6 C5 H5A 119.1 . . ?
C5 C6 N1 125.4(3) . . ?
C5 C6 C1 121.0(4) . . ?
N1 C6 C1 113.6(3) . . ?
C7 N1 C6 123.5(3) . . ?
C7 N1 Zn1 126.2(3) . . ?
C6 N1 Zn1 110.1(2) . . ?
N1 C7 C8 127.2(4) . . ?
N1 C7 H7A 116.4 . . ?
C8 C7 H7A 116.4 . . ?
C9 C8 C13 117.0(4) . . ?
C9 C8 C7 116.3(4) . . ?
C13 C8 C7 126.6(4) . . ?
C8 C9 C10 121.6(4) . . ?
C8 C9 H9A 119.2 . . ?
C10 C9 H9A 119.2 . . ?
C11 C10 C9 120.8(4) . . ?
C11 C10 H10A 119.6 . . ?
C9 C10 H10A 119.6 . . ?
C10 C11 C12 119.8(4) . . ?
C10 C11 H11A 120.1 . . ?
C12 C11 H11A 120.1 . . ?
C11 C12 C13 120.3(4) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C12 C13 N2 121.6(4) . . ?
C12 C13 C8 120.5(4) . . ?
N2 C13 C8 117.9(3) . . ?
C14 N2 C13 121.8(3) . . ?
C14 N2 Zn1 114.2(3) . . ?
C13 N2 Zn1 124.0(3) . . ?
N2 C14 C15 119.1(4) . . ?
N2 C14 H14A 120.5 . . ?
C15 C14 H14A 120.5 . . ?
N3 C15 C16 122.2(4) . . ?
N3 C15 C14 115.6(4) . . ?
C16 C15 C14 122.1(4) . . ?
C15 C16 C17 118.9(5) . . ?
C15 C16 H16A 120.5 . . ?
C17 C16 H16A 120.5 . . ?
C16 C17 C18 118.4(5) . . ?
C16 C17 H17A 120.8 . . ?
C18 C17 H17A 120.8 . . ?
C19 C18 C17 119.1(5) . . ?
C19 C18 H18A 120.5 . . ?
C17 C18 H18A 120.5 . . ?
N3 C19 C18 122.0(5) . . ?
N3 C19 H19A 119.0 . . ?
C18 C19 H19A 119.0 . . ?
C19 N3 C15 119.5(4) . . ?
C19 N3 Zn1 126.4(3) . . ?
C15 N3 Zn1 114.2(3) . . ?
C21 C20 C23 110.1(4) . . ?
C21 C20 C2 108.3(4) . . ?
C23 C20 C2 110.1(4) . . ?
C21 C20 C22 108.3(4) . . ?
C23 C20 C22 108.1(4) . . ?
C2 C20 C22 111.9(4) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C27 C24 C25 111.4(5) . . ?
C27 C24 C4 110.0(4) . . ?
C25 C24 C4 113.3(4) . . ?
C27 C24 C26 107.7(6) . . ?
C25 C24 C26 105.4(5) . . ?
C4 C24 C26 108.7(4) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C28 O2 Zn1 129.3(3) . . ?
O2 C28 O3 125.0(6) . . ?
O2 C28 C29 118.5(5) . . ?
O3 C28 C29 116.5(6) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
H1W1 O1W H2W1 124.1(12) . . ?

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
Zn1 O1 C1 C6 0.5(5) . . . . ?
Zn1 O1 C1 C2 179.6(3) . . . . ?
O1 C1 C2 C3 179.4(4) . . . . ?
C6 C1 C2 C3 -1.4(5) . . . . ?
O1 C1 C2 C20 -1.7(6) . . . . ?
C6 C1 C2 C20 177.4(4) . . . . ?
C1 C2 C3 C4 0.6(6) . . . . ?
C20 C2 C3 C4 -178.2(4) . . . . ?
C2 C3 C4 C5 0.1(7) . . . . ?
C2 C3 C4 C24 -178.2(4) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C24 C4 C5 C6 178.4(4) . . . . ?
C4 C5 C6 N1 -177.5(4) . . . . ?
C4 C5 C6 C1 -1.0(6) . . . . ?
O1 C1 C6 C5 -179.2(4) . . . . ?
C2 C1 C6 C5 1.6(6) . . . . ?
O1 C1 C6 N1 -2.3(5) . . . . ?
C2 C1 C6 N1 178.5(3) . . . . ?
C5 C6 N1 C7 -5.8(6) . . . . ?
C1 C6 N1 C7 177.5(4) . . . . ?
C5 C6 N1 Zn1 179.5(3) . . . . ?
C1 C6 N1 Zn1 2.8(4) . . . . ?
C6 N1 C7 C8 178.1(4) . . . . ?
Zn1 N1 C7 C8 -8.0(6) . . . . ?
N1 C7 C8 C9 169.2(4) . . . . ?
N1 C7 C8 C13 -13.9(7) . . . . ?
C13 C8 C9 C10 1.9(6) . . . . ?
C7 C8 C9 C10 179.1(4) . . . . ?
C8 C9 C10 C11 -1.4(7) . . . . ?
C9 C10 C11 C12 0.7(7) . . . . ?
C10 C11 C12 C13 -0.6(7) . . . . ?
C11 C12 C13 N2 -177.3(4) . . . . ?
C11 C12 C13 C8 1.3(6) . . . . ?
C9 C8 C13 C12 -1.9(6) . . . . ?
C7 C8 C13 C12 -178.8(4) . . . . ?
C9 C8 C13 N2 176.8(4) . . . . ?
C7 C8 C13 N2 -0.1(6) . . . . ?
C12 C13 N2 C14 28.9(6) . . . . ?
C8 C13 N2 C14 -149.8(4) . . . . ?
C12 C13 N2 Zn1 -149.2(3) . . . . ?
C8 C13 N2 Zn1 32.2(5) . . . . ?
C13 N2 C14 C15 178.2(4) . . . . ?
Zn1 N2 C14 C15 -3.6(5) . . . . ?
N2 C14 C15 N3 -0.2(6) . . . . ?
N2 C14 C15 C16 -176.5(4) . . . . ?
N3 C15 C16 C17 1.0(8) . . . . ?
C14 C15 C16 C17 177.1(4) . . . . ?
C15 C16 C17 C18 -1.2(8) . . . . ?
C16 C17 C18 C19 1.2(9) . . . . ?
C17 C18 C19 N3 -1.1(9) . . . . ?
C18 C19 N3 C15 0.9(8) . . . . ?
C18 C19 N3 Zn1 179.6(4) . . . . ?
C16 C15 N3 C19 -0.9(7) . . . . ?
C14 C15 N3 C19 -177.2(4) . . . . ?
C16 C15 N3 Zn1 -179.7(4) . . . . ?
C14 C15 N3 Zn1 4.0(5) . . . . ?
C3 C2 C20 C21 117.9(4) . . . . ?
C1 C2 C20 C21 -60.9(5) . . . . ?
C3 C2 C20 C23 -121.7(5) . . . . ?
C1 C2 C20 C23 59.5(5) . . . . ?
C3 C2 C20 C22 -1.4(6) . . . . ?
C1 C2 C20 C22 179.7(4) . . . . ?
C5 C4 C24 C27 70.2(7) . . . . ?
C3 C4 C24 C27 -111.5(6) . . . . ?
C5 C4 C24 C25 -164.3(5) . . . . ?
C3 C4 C24 C25 13.9(7) . . . . ?
C5 C4 C24 C26 -47.5(6) . . . . ?
C3 C4 C24 C26 130.7(5) . . . . ?
Zn1 O2 C28 O3 175.7(4) . . . . ?
Zn1 O2 C28 C29 -0.6(8) . . . . ?

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
C7 H7A O1W 0.93 2.45 3.341(11) 159.6 1_565
C14 H14A O2 0.93 2.66 3.304(5) 127.2 2_766
C14 H14A O1W 0.93 2.43 3.144(11) 133.8 2_766
C16 H16A O3 0.93 2.50 3.380(7) 158.9 2_766
O1W H1W1 O3 0.852(9) 1.939(4) 2.791(10) 179.3(8) 2_656
O1W H2W1 O3 0.910(10) 1.716(6) 2.548(11) 150.6(7) .

_refine_diff_density_max         0.900
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.127

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_e1311a
_database_code_depnum_ccdc_archive 'CCDC 1497260'
_audit_update_record             
;
2016-08-02 deposited with the CCDC.
2017-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H30 Br N3 O Zn'
_chemical_formula_sum            'C27 H30 Br N3 O Zn'
_chemical_formula_weight         557.82

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                   7.9476(3)
_cell_length_b                   11.5809(5)
_cell_length_c                   14.2737(6)
_cell_angle_alpha                83.054(4)
_cell_angle_beta                 76.725(4)
_cell_angle_gamma                89.507(3)
_cell_volume                     1269.02(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4061
_cell_measurement_theta_min      2.1579
_cell_measurement_theta_max      28.2955

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             572
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.661
_exptl_crystal_size_mid          0.326
_exptl_crystal_size_min          0.186
_exptl_absorpt_coefficient_mu    2.566
_shelx_estimated_absorpt_T_min   0.282
_shelx_estimated_absorpt_T_max   0.647
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.338022
_exptl_absorpt_correction_T_max  0.686286
_exptl_absorpt_process_details   'Oxford Diffraction CrysAlis'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Oxford Sapphire CCD'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean 8.2564
_diffrn_reflns_number            8731
_diffrn_reflns_av_unetI/netI     0.0667
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.442
_diffrn_reflns_theta_max         28.367
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5668
_reflns_number_gt                3707
_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       'Oxford Diffraction CrysAlis'
_computing_cell_refinement       'Oxford Diffraction CrysAlis'
_computing_data_reduction        'Oxford Diffraction CrysAlis'
_computing_structure_solution    'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'

_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)+(0.0448P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5668
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0859
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   0.882
_refine_ls_restrained_S_all      0.882
_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_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 0.13915(4) 0.71982(3) 0.57389(2) 0.03399(10) Uani 1 1 d . . . . .
Br1 Br 0.01040(4) 0.68817(3) 0.44236(2) 0.04354(11) Uani 1 1 d . . . . .
O1 O -0.0278(3) 0.69815(17) 0.69948(15) 0.0445(5) Uani 1 1 d . . . . .
C1 C -0.0589(3) 0.7917(2) 0.7431(2) 0.0320(6) Uani 1 1 d . . . . .
C2 C -0.1610(4) 0.7902(2) 0.8390(2) 0.0344(7) Uani 1 1 d . . . . .
C3 C -0.1898(4) 0.8941(3) 0.8775(2) 0.0383(7) Uani 1 1 d . . . . .
H3A H -0.2575 0.8921 0.9402 0.046 Uiso 1 1 calc R U . . .
C4 C -0.1241(4) 1.0027(2) 0.8286(2) 0.0355(7) Uani 1 1 d . . . . .
C5 C -0.0250(3) 1.0034(2) 0.7356(2) 0.0334(6) Uani 1 1 d . . . . .
H5A H 0.0193 1.0737 0.7003 0.040 Uiso 1 1 calc R U . . .
C6 C 0.0098(3) 0.9016(2) 0.6938(2) 0.0307(6) Uani 1 1 d . . . . .
C7 C 0.1816(3) 0.9828(2) 0.5404(2) 0.0328(6) Uani 1 1 d . . . . .
H7A H 0.1373 1.0552 0.5536 0.039 Uiso 1 1 calc R U . . .
N1 N 0.1210(3) 0.89420(19) 0.60259(17) 0.0319(5) Uani 1 1 d . . . . .
C8 C 0.3140(3) 0.9793(2) 0.4509(2) 0.0293(6) Uani 1 1 d . . . . .
C9 C 0.3429(4) 1.0807(3) 0.3857(2) 0.0382(7) Uani 1 1 d . . . . .
H9A H 0.2729 1.1441 0.3993 0.046 Uiso 1 1 calc R U . . .
C10 C 0.4706(4) 1.0905(3) 0.3022(2) 0.0459(8) Uani 1 1 d . . . . .
H10A H 0.4862 1.1594 0.2601 0.055 Uiso 1 1 calc R U . . .
C11 C 0.5764(4) 0.9968(3) 0.2810(2) 0.0479(8) Uani 1 1 d . . . . .
H11A H 0.6642 1.0029 0.2248 0.057 Uiso 1 1 calc R U . . .
C12 C 0.5513(4) 0.8946(3) 0.3433(2) 0.0395(7) Uani 1 1 d . . . . .
H12A H 0.6218 0.8317 0.3287 0.047 Uiso 1 1 calc R U . . .
C13 C 0.4220(3) 0.8851(2) 0.4275(2) 0.0308(6) Uani 1 1 d . . . . .
N2 N 0.3944(3) 0.77954(19) 0.49147(16) 0.0307(5) Uani 1 1 d . . . . .
C14 C 0.5167(4) 0.7147(2) 0.5082(2) 0.0348(7) Uani 1 1 d . . . . .
H14A H 0.6308 0.7342 0.4773 0.042 Uiso 1 1 calc R U . . .
C15 C 0.4749(4) 0.6085(2) 0.5771(2) 0.0331(6) Uani 1 1 d . . . . .
C16 C 0.6006(4) 0.5368(3) 0.6034(2) 0.0433(8) Uani 1 1 d . . . . .
H16A H 0.7172 0.5526 0.5760 0.052 Uiso 1 1 calc R U . . .
C17 C 0.5486(4) 0.4410(3) 0.6716(2) 0.0494(8) Uani 1 1 d . . . . .
H17A H 0.6300 0.3902 0.6897 0.059 Uiso 1 1 calc R U . . .
C18 C 0.3761(5) 0.4214(3) 0.7122(3) 0.0512(9) Uani 1 1 d . . . . .
H18A H 0.3391 0.3588 0.7597 0.061 Uiso 1 1 calc R U . . .
C19 C 0.2572(4) 0.4967(3) 0.6812(2) 0.0446(8) Uani 1 1 d . . . . .
H19A H 0.1399 0.4819 0.7073 0.054 Uiso 1 1 calc R U . . .
N3 N 0.3046(3) 0.5887(2) 0.61575(18) 0.0365(6) Uani 1 1 d . . . . .
C20 C -0.2320(4) 0.6737(3) 0.8973(2) 0.0465(8) Uani 1 1 d . . . . .
C21 C -0.3357(6) 0.6887(3) 0.9986(3) 0.0755(12) Uani 1 1 d . . . . .
H21A H -0.2641 0.7253 1.0327 0.091 Uiso 1 1 calc R U . . .
H21B H -0.4336 0.7364 0.9940 0.091 Uiso 1 1 calc R U . . .
H21C H -0.3750 0.6139 1.0331 0.091 Uiso 1 1 calc R U . . .
C22 C -0.3501(6) 0.6156(3) 0.8460(3) 0.0809(13) Uani 1 1 d . . . . .
H22A H -0.2876 0.6050 0.7817 0.097 Uiso 1 1 calc R U . . .
H22B H -0.3893 0.5413 0.8816 0.097 Uiso 1 1 calc R U . . .
H22C H -0.4478 0.6638 0.8425 0.097 Uiso 1 1 calc R U . . .
C23 C -0.0808(6) 0.5955(4) 0.9092(3) 0.0878(14) Uani 1 1 d . . . . .
H23A H -0.0120 0.5840 0.8465 0.105 Uiso 1 1 calc R U . . .
H23B H -0.0109 0.6316 0.9446 0.105 Uiso 1 1 calc R U . . .
H23C H -0.1244 0.5217 0.9441 0.105 Uiso 1 1 calc R U . . .
C24 C -0.1635(4) 1.1157(3) 0.8742(2) 0.0406(7) Uani 1 1 d . . . . .
C25 C -0.0009(5) 1.1936(3) 0.8516(3) 0.0692(11) Uani 1 1 d . . . . .
H25A H 0.0440 1.2069 0.7827 0.083 Uiso 1 1 calc R U . . .
H25B H -0.0295 1.2667 0.8761 0.083 Uiso 1 1 calc R U . . .
H25C H 0.0846 1.1561 0.8818 0.083 Uiso 1 1 calc R U . . .
C26 C -0.2296(5) 1.0973(3) 0.9837(2) 0.0612(10) Uani 1 1 d . . . . .
H26A H -0.2517 1.1713 1.0075 0.073 Uiso 1 1 calc R U . . .
H26B H -0.3346 1.0514 1.0001 0.073 Uiso 1 1 calc R U . . .
H26C H -0.1442 1.0575 1.0127 0.073 Uiso 1 1 calc R U . . .
C27 C -0.3017(5) 1.1822(3) 0.8294(3) 0.0616(10) Uani 1 1 d . . . . .
H27A H -0.2620 1.1946 0.7601 0.074 Uiso 1 1 calc R U . . .
H27B H -0.4077 1.1374 0.8464 0.074 Uiso 1 1 calc R U . . .
H27C H -0.3212 1.2559 0.8540 0.074 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
Zn1 O1 1.960(2) . ?
Zn1 N1 2.106(2) . ?
Zn1 N3 2.121(2) . ?
Zn1 N2 2.170(2) . ?
Zn1 Br1 2.4002(4) . ?
O1 C1 1.308(3) . ?
C1 C2 1.421(4) . ?
C1 C6 1.425(4) . ?
C2 C3 1.378(4) . ?
C2 C20 1.535(4) . ?
C3 C4 1.405(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.379(4) . ?
C4 C24 1.529(4) . ?
C5 C6 1.383(4) . ?
C5 H5A 0.9300 . ?
C6 N1 1.407(3) . ?
C7 N1 1.291(3) . ?
C7 C8 1.461(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.393(4) . ?
C8 C13 1.406(4) . ?
C9 C10 1.370(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.387(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.377(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.384(4) . ?
C12 H12A 0.9300 . ?
C13 N2 1.421(3) . ?
N2 C14 1.271(3) . ?
C14 C15 1.467(4) . ?
C14 H14A 0.9300 . ?
C15 N3 1.349(3) . ?
C15 C16 1.383(4) . ?
C16 C17 1.382(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.369(5) . ?
C17 H17A 0.9300 . ?
C18 C19 1.391(4) . ?
C18 H18A 0.9300 . ?
C19 N3 1.324(4) . ?
C19 H19A 0.9300 . ?
C20 C21 1.521(5) . ?
C20 C22 1.521(5) . ?
C20 C23 1.526(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C26 1.520(4) . ?
C24 C25 1.532(4) . ?
C24 C27 1.548(4) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
O1 Zn1 N1 81.11(8) . . ?
O1 Zn1 N3 93.67(9) . . ?
N1 Zn1 N3 129.02(8) . . ?
O1 Zn1 N2 148.00(8) . . ?
N1 Zn1 N2 82.04(8) . . ?
N3 Zn1 N2 76.36(9) . . ?
O1 Zn1 Br1 112.25(6) . . ?
N1 Zn1 Br1 111.95(6) . . ?
N3 Zn1 Br1 116.75(6) . . ?
N2 Zn1 Br1 99.24(6) . . ?
C1 O1 Zn1 115.04(17) . . ?
O1 C1 C2 123.0(2) . . ?
O1 C1 C6 119.9(3) . . ?
C2 C1 C6 117.1(2) . . ?
C3 C2 C1 118.5(3) . . ?
C3 C2 C20 122.1(3) . . ?
C1 C2 C20 119.5(3) . . ?
C2 C3 C4 124.5(3) . . ?
C2 C3 H3A 117.7 . . ?
C4 C3 H3A 117.7 . . ?
C5 C4 C3 116.7(3) . . ?
C5 C4 C24 121.0(3) . . ?
C3 C4 C24 122.3(3) . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5A 119.4 . . ?
C6 C5 H5A 119.4 . . ?
C5 C6 N1 124.5(2) . . ?
C5 C6 C1 121.9(3) . . ?
N1 C6 C1 113.5(2) . . ?
N1 C7 C8 125.6(3) . . ?
N1 C7 H7A 117.2 . . ?
C8 C7 H7A 117.2 . . ?
C7 N1 C6 124.4(2) . . ?
C7 N1 Zn1 124.89(19) . . ?
C6 N1 Zn1 110.02(17) . . ?
C9 C8 C13 117.1(3) . . ?
C9 C8 C7 117.0(3) . . ?
C13 C8 C7 125.8(2) . . ?
C10 C9 C8 122.5(3) . . ?
C10 C9 H9A 118.8 . . ?
C8 C9 H9A 118.8 . . ?
C9 C10 C11 119.4(3) . . ?
C9 C10 H10A 120.3 . . ?
C11 C10 H10A 120.3 . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11A 120.0 . . ?
C10 C11 H11A 120.0 . . ?
C11 C12 C13 120.4(3) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C12 C13 C8 120.6(3) . . ?
C12 C13 N2 120.7(3) . . ?
C8 C13 N2 118.7(2) . . ?
C14 N2 C13 123.2(2) . . ?
C14 N2 Zn1 114.38(19) . . ?
C13 N2 Zn1 122.38(16) . . ?
N2 C14 C15 119.0(3) . . ?
N2 C14 H14A 120.5 . . ?
C15 C14 H14A 120.5 . . ?
N3 C15 C16 122.5(3) . . ?
N3 C15 C14 114.9(2) . . ?
C16 C15 C14 122.6(3) . . ?
C17 C16 C15 118.3(3) . . ?
C17 C16 H16A 120.8 . . ?
C15 C16 H16A 120.8 . . ?
C18 C17 C16 119.4(3) . . ?
C18 C17 H17A 120.3 . . ?
C16 C17 H17A 120.3 . . ?
C17 C18 C19 118.9(3) . . ?
C17 C18 H18A 120.6 . . ?
C19 C18 H18A 120.6 . . ?
N3 C19 C18 122.5(3) . . ?
N3 C19 H19A 118.8 . . ?
C18 C19 H19A 118.8 . . ?
C19 N3 C15 118.3(3) . . ?
C19 N3 Zn1 126.1(2) . . ?
C15 N3 Zn1 115.31(19) . . ?
C21 C20 C22 107.7(3) . . ?
C21 C20 C23 107.1(3) . . ?
C22 C20 C23 110.5(3) . . ?
C21 C20 C2 112.1(3) . . ?
C22 C20 C2 110.3(3) . . ?
C23 C20 C2 109.0(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C26 C24 C4 113.7(3) . . ?
C26 C24 C25 107.5(3) . . ?
C4 C24 C25 110.4(3) . . ?
C26 C24 C27 108.4(3) . . ?
C4 C24 C27 108.8(2) . . ?
C25 C24 C27 107.8(3) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 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
Zn1 O1 C1 C2 -172.8(2) . . . . ?
Zn1 O1 C1 C6 7.7(3) . . . . ?
O1 C1 C2 C3 -178.3(3) . . . . ?
C6 C1 C2 C3 1.2(4) . . . . ?
O1 C1 C2 C20 3.1(4) . . . . ?
C6 C1 C2 C20 -177.4(2) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C20 C2 C3 C4 178.1(3) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C2 C3 C4 C24 178.6(3) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C24 C4 C5 C6 -179.4(3) . . . . ?
C4 C5 C6 N1 -174.5(3) . . . . ?
C4 C5 C6 C1 2.0(4) . . . . ?
O1 C1 C6 C5 177.6(2) . . . . ?
C2 C1 C6 C5 -2.0(4) . . . . ?
O1 C1 C6 N1 -5.5(4) . . . . ?
C2 C1 C6 N1 174.9(2) . . . . ?
C8 C7 N1 C6 171.7(2) . . . . ?
C8 C7 N1 Zn1 -19.1(4) . . . . ?
C5 C6 N1 C7 -11.8(4) . . . . ?
C1 C6 N1 C7 171.4(2) . . . . ?
C5 C6 N1 Zn1 177.6(2) . . . . ?
C1 C6 N1 Zn1 0.8(3) . . . . ?
N1 C7 C8 C9 170.1(3) . . . . ?
N1 C7 C8 C13 -14.1(4) . . . . ?
C13 C8 C9 C10 -0.3(4) . . . . ?
C7 C8 C9 C10 175.9(3) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C12 0.7(5) . . . . ?
C10 C11 C12 C13 -0.6(4) . . . . ?
C11 C12 C13 C8 0.0(4) . . . . ?
C11 C12 C13 N2 179.4(3) . . . . ?
C9 C8 C13 C12 0.4(4) . . . . ?
C7 C8 C13 C12 -175.4(3) . . . . ?
C9 C8 C13 N2 -179.0(2) . . . . ?
C7 C8 C13 N2 5.3(4) . . . . ?
C12 C13 N2 C14 36.8(4) . . . . ?
C8 C13 N2 C14 -143.9(3) . . . . ?
C12 C13 N2 Zn1 -146.0(2) . . . . ?
C8 C13 N2 Zn1 33.3(3) . . . . ?
C13 N2 C14 C15 178.8(2) . . . . ?
Zn1 N2 C14 C15 1.4(3) . . . . ?
N2 C14 C15 N3 1.1(4) . . . . ?
N2 C14 C15 C16 -176.3(3) . . . . ?
N3 C15 C16 C17 0.4(5) . . . . ?
C14 C15 C16 C17 177.6(3) . . . . ?
C15 C16 C17 C18 -1.4(5) . . . . ?
C16 C17 C18 C19 2.1(5) . . . . ?
C17 C18 C19 N3 -2.0(5) . . . . ?
C18 C19 N3 C15 1.0(5) . . . . ?
C18 C19 N3 Zn1 -172.8(2) . . . . ?
C16 C15 N3 C19 -0.2(4) . . . . ?
C14 C15 N3 C19 -177.6(2) . . . . ?
C16 C15 N3 Zn1 174.3(2) . . . . ?
C14 C15 N3 Zn1 -3.1(3) . . . . ?
C3 C2 C20 C21 0.6(4) . . . . ?
C1 C2 C20 C21 179.2(3) . . . . ?
C3 C2 C20 C22 120.7(3) . . . . ?
C1 C2 C20 C22 -60.8(4) . . . . ?
C3 C2 C20 C23 -117.8(3) . . . . ?
C1 C2 C20 C23 60.8(4) . . . . ?
C5 C4 C24 C26 -163.9(3) . . . . ?
C3 C4 C24 C26 17.9(4) . . . . ?
C5 C4 C24 C25 -43.1(4) . . . . ?
C3 C4 C24 C25 138.7(3) . . . . ?
C5 C4 C24 C27 75.1(4) . . . . ?
C3 C4 C24 C27 -103.1(3) . . . . ?

_refine_diff_density_max         0.479
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.081

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
