# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_alpha_Zn
_database_code_depnum_ccdc_archive 'CCDC 1813598'
_audit_update_record             
;
2017-12-28 deposited with the CCDC.
2018-05-16 downloaded from the CCDC.
;
_audit_creation_date             2017-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 N O4 Zn'
_chemical_formula_sum            'C16 H13 N O4 Zn'
_chemical_formula_weight         348.64
_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 0.0181 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'
O O 0.0492 0.0322 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   41.740(4)
_cell_length_b                   41.740(4)
_cell_length_c                   9.9584(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     15025(4)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    3497
_cell_measurement_temperature    203
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      32.4
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.093
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    0.694
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       Prism
_exptl_crystal_F_000             3204
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            27125
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        62.991
_diffrn_reflns_theta_max         62.991
_diffrn_reflns_theta_min         6.948
_diffrn_ambient_temperature      203(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5169
_reflns_number_total             5370
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         5370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0708P)²+20.0439P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1292
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b), C12(H12a,H12b)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C11(H11), C15(H15), C16(H16), C10(H10), C6(H6), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.02658(2) 0.49064(2) 0.06865(3) 0.03120(14) Uani 1 1 d . . . . .
N1 N 0.06094(5) 0.47613(5) 0.16855(18) 0.0358(4) Uani 1 1 d . . . . .
H1 H 0.0454 0.4561 0.2307 0.043 Uiso 1 1 calc R . . . .
O1 O -0.01061(5) 0.48492(5) 0.21255(16) 0.0491(4) Uani 1 1 d . . . . .
O2 O 0.05241(5) 0.54630(4) 0.09211(17) 0.0488(4) Uani 1 1 d . . . . .
O3 O -0.01255(5) 0.43956(4) -0.0005(2) 0.0608(5) Uani 1 1 d . . . . .
O4 O 0.04906(5) 0.49913(5) -0.11956(16) 0.0527(4) Uani 1 1 d . . . . .
C1 C -0.03620(6) 0.49214(6) 0.2184(2) 0.0381(5) Uani 1 1 d . . . . .
C8 C 0.04162(7) 0.56852(6) 0.0620(2) 0.0418(5) Uani 1 1 d . . . . .
C5 C -0.07866(6) 0.49176(7) 0.6108(2) 0.0413(5) Uani 1 1 d . . . . .
C3 C -0.04545(7) 0.47392(6) 0.4597(2) 0.0427(5) Uani 1 1 d . . . . .
H3 H -0.0315 0.4625 0.4459 0.051 Uiso 1 1 calc R . . . .
C2 C -0.05242(6) 0.49046(6) 0.3537(2) 0.0386(5) Uani 1 1 d . . . . .
C14 C 0.09308(7) 0.43956(7) 0.1273(2) 0.0447(6) Uani 1 1 d . . . . .
C9 C 0.06508(7) 0.60780(6) 0.1078(3) 0.0439(6) Uani 1 1 d . . . . .
C4 C -0.05879(7) 0.47388(7) 0.5869(2) 0.0440(5) Uani 1 1 d . . . . .
H4 H -0.0544 0.4618 0.6568 0.053 Uiso 1 1 calc R . . . .
C13 C 0.07535(7) 0.46022(7) 0.0669(2) 0.0459(6) Uani 1 1 d . . . . .
H13A H 0.0934 0.4801 0.0111 0.055 Uiso 1 1 calc R . . . .
H13B H 0.0551 0.4435 0.0093 0.055 Uiso 1 1 calc R . . . .
C11 C 0.09785(7) 0.61907(7) 0.1761(3) 0.0522(6) Uani 1 1 d . . . . .
H11 H 0.1063 0.6025 0.1894 0.063 Uiso 1 1 calc R . . . .
C15 C 0.13006(8) 0.45146(8) 0.1086(3) 0.0555(7) Uani 1 1 d . . . . .
H15 H 0.1449 0.4734 0.0627 0.067 Uiso 1 1 calc R . . . .
C12 C 0.09155(6) 0.50600(7) 0.2502(2) 0.0435(5) Uani 1 1 d . . . . .
H12A H 0.1006 0.5296 0.2052 0.052 Uiso 1 1 calc R . . . .
H12B H 0.1119 0.5011 0.2566 0.052 Uiso 1 1 calc R . . . .
C16 C 0.07183(8) 0.40729(9) 0.1972(4) 0.0671(9) Uani 1 1 d . . . . .
H16 H 0.0468 0.3989 0.2112 0.080 Uiso 1 1 calc R . . . .
C10 C 0.05378(8) 0.63306(7) 0.0862(4) 0.0688(9) Uani 1 1 d . . . . .
H10 H 0.0323 0.6262 0.0375 0.083 Uiso 1 1 calc R . . . .
C6 C -0.08619(9) 0.50781(9) 0.5038(3) 0.0645(8) Uani 1 1 d . . . . .
H6 H -0.1000 0.5194 0.5176 0.077 Uiso 1 1 calc R . . . .
C7 C -0.07354(9) 0.50707(9) 0.3764(3) 0.0643(8) Uani 1 1 d . . . . .
H7 H -0.0792 0.5178 0.3053 0.077 Uiso 1 1 calc R . . . .


_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 Zn1 3.0229(6) 10_565 ?
Zn1 N1 2.0693(17) . ?
Zn1 O1 2.0371(17) . ?
Zn1 O2 2.0273(15) . ?
Zn1 O3 2.0507(16) . ?
Zn1 O4 2.0461(17) . ?
N1 C13 1.492(3) . ?
N1 C12 1.501(3) . ?
O1 C1 1.248(3) . ?
O2 C8 1.253(3) . ?
O3 C8 1.246(3) 10_565 ?
O4 C1 1.259(3) 10_565 ?
C1 O4 1.259(3) 10_565 ?
C1 C2 1.494(3) . ?
C8 O3 1.246(3) 10_565 ?
C8 C9 1.500(3) . ?
C5 C4 1.386(3) . ?
C5 C12 1.505(3) 10_566 ?
C5 C6 1.376(4) . ?
C3 C2 1.370(3) . ?
C3 C4 1.383(3) . ?
C2 C7 1.386(3) . ?
C14 C13 1.514(3) . ?
C14 C15 1.378(4) . ?
C14 C16 1.375(4) . ?
C9 C11 1.383(4) . ?
C9 C10 1.370(4) . ?
C11 C15 1.381(3) 14_455 ?
C15 C11 1.381(3) 15 ?
C12 C5 1.505(3) 10_566 ?
C16 C10 1.387(4) 15 ?
C10 C16 1.387(4) 14_455 ?
C6 C7 1.381(4) . ?

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
N1 Zn1 Zn1 177.28(6) . 10_565 ?
O1 Zn1 Zn1 74.55(5) . 10_565 ?
O1 Zn1 N1 103.10(7) . . ?
O1 Zn1 O3 87.15(8) . . ?
O1 Zn1 O4 157.11(7) . . ?
O2 Zn1 Zn1 78.14(5) . 10_565 ?
O2 Zn1 N1 103.34(7) . . ?
O2 Zn1 O1 89.47(7) . . ?
O2 Zn1 O3 157.07(7) . . ?
O2 Zn1 O4 88.39(7) . . ?
O3 Zn1 Zn1 79.10(5) . 10_565 ?
O3 Zn1 N1 99.51(7) . . ?
O4 Zn1 Zn1 82.71(5) . 10_565 ?
O4 Zn1 N1 99.57(7) . . ?
O4 Zn1 O3 86.01(8) . . ?
C13 N1 Zn1 107.25(13) . . ?
C13 N1 C12 111.83(18) . . ?
C12 N1 Zn1 116.35(13) . . ?
C1 O1 Zn1 134.31(15) . . ?
C8 O2 Zn1 129.67(15) . . ?
C8 O3 Zn1 127.46(15) 10_565 . ?
C1 O4 Zn1 122.77(16) 10_565 . ?
O1 C1 O4 125.0(2) . 10_565 ?
O1 C1 C2 116.94(19) . . ?
O4 C1 C2 118.0(2) 10_565 . ?
O2 C8 C9 117.1(2) . . ?
O3 C8 O2 125.4(2) 10_565 . ?
O3 C8 C9 117.4(2) 10_565 . ?
C4 C5 C12 121.4(2) . 10_566 ?
C6 C5 C4 118.2(2) . . ?
C6 C5 C12 120.4(2) . 10_566 ?
C2 C3 C4 121.3(2) . . ?
C3 C2 C1 120.9(2) . . ?
C3 C2 C7 118.3(2) . . ?
C7 C2 C1 120.7(2) . . ?
C15 C14 C13 121.3(2) . . ?
C16 C14 C13 120.0(2) . . ?
C16 C14 C15 118.6(2) . . ?
C11 C9 C8 121.1(2) . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 C11 118.5(2) . . ?
C3 C4 C5 120.4(2) . . ?
N1 C13 C14 113.87(19) . . ?
C15 C11 C9 120.5(2) 14_455 . ?
C14 C15 C11 120.8(2) . 15 ?
N1 C12 C5 111.55(19) . 10_566 ?
C14 C16 C10 120.5(3) . 15 ?
C9 C10 C16 120.9(3) . 14_455 ?
C5 C6 C7 121.2(2) . . ?
C6 C7 C2 120.5(2) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_beta_Zn
_database_code_depnum_ccdc_archive 'CCDC 1813599'
_audit_update_record             
;
2017-12-28 deposited with the CCDC.
2018-05-16 downloaded from the CCDC.
;
_audit_creation_date             2017-12-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.11(C432 H351 N27 O108 Zn27)'
_chemical_formula_sum            'C48 H39 N3 O12 Zn3'
_chemical_formula_weight         1045.93
_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 0.0181 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'
O O 0.0492 0.0322 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   42.4897(8)
_cell_length_b                   42.4897(8)
_cell_length_c                   10.4000(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     16260.4(9)
_cell_formula_units_Z            9
_cell_measurement_reflns_used    1786
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      40.4
_cell_measurement_theta_min      6.7
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.515
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.961
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             4806
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       50
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            29635
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.482
_diffrn_reflns_theta_max         67.482
_diffrn_reflns_theta_min         2.079
_diffrn_ambient_temperature      203
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5024
_reflns_number_total             6487
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.537
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         6487
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0608
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1567P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2030
_refine_ls_wR_factor_ref         0.2140
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 C24B-N2
 1.48 with sigma of 0.02
 C21B-C24B
 1.48 with sigma of 0.02
 C24A-C21A
 1.48 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C19A) = Uanis(C18A) = Uanis(C23A) = Uanis(C22A) = Uanis(C21A) =
Uanis(C20A) = Uanis(C24A) = Uanis(C19B) = Uanis(C18B) = Uanis(C23B) =
Uanis(C20B) = Uanis(C21B) = Uanis(C22B) = Uanis(C24B)
4. Others
 Fixed Sof: C17B(0.5) C19B(0.5) H19B(0.5) C18B(0.5) C23B(0.5) H23B(0.5)
 C22B(0.5) H22B(0.5) C21B(0.5) C20B(0.5) H20B(0.5) N2(0.5) H2(0.5) C19A(0.5)
 H19A(0.5) C18A(0.5) C23A(0.5) H23A(0.5) C22A(0.5) H22A(0.5) C21A(0.5)
 C20A(0.5) H20A(0.5) C24B(0.5) H24A(0.5) H24B(0.5) C24A(0.5) H24C(0.5)
 H24D(0.5) C17A(0.5)
5.a Ternary CH refined with riding coordinates:
 N1(H1)
5.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C8(H8A,H8B), C24B(H24A,H24B), C24A(H24C,H24D)
5.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C14(H14), C3(H3), C12(H12), C11(H11), C15(H15), C4(H4),
 C19B(H19B), C23B(H23B), C22B(H22B), C20B(H20B), N2(H2), C19A(H19A), C23A(H23A),
  C22A(H22A), C20A(H20A)
5.d Fitted hexagon refined as free rotating group:
 C19B(C18B,C23B,C22B,C21B,C20B), C19A(C18A,C23A,C22A,C21A,C20A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.8333 0.6667 0.1667 0.0683(2) Uani 1 2 d S T P . .
Zn2 Zn 0.76210(2) 0.62789(2) -0.01921(4) 0.0728(2) Uani 1 1 d . . . . .
O2 O 0.65777(8) 0.84075(7) 0.0366(2) 0.0779(6) Uani 1 1 d . . . . .
O4 O 0.74197(7) 0.64744(8) 0.1059(2) 0.0867(8) Uani 1 1 d . . . . .
O3 O 0.79395(7) 0.67857(9) 0.2139(2) 0.0856(8) Uani 1 1 d . . . . .
O1 O 0.67886(9) 0.88863(8) 0.1622(3) 0.0925(8) Uani 1 1 d . . . . .
O6 O 0.76071(8) 0.58403(8) 0.0482(3) 0.0932(8) Uani 1 1 d . . . . .
O5 O 0.80067(8) 0.61245(9) 0.2082(3) 0.0898(8) Uani 1 1 d . . . . .
N1 N 0.73079(9) 0.78071(8) 0.5330(3) 0.0699(7) Uani 1 1 d . . . . .
H1 H 0.7462 0.7761 0.5910 0.084 Uiso 1 1 calc R . . . .
C13 C 0.74529(10) 0.68686(10) 0.2722(3) 0.0692(8) Uani 1 1 d . . . . .
C2 C 0.70053(10) 0.84777(9) 0.2013(3) 0.0703(8) Uani 1 1 d . . . . .
C1 C 0.67905(11) 0.86075(10) 0.1297(3) 0.0739(9) Uani 1 1 d . . . . .
C16 C 0.76180(10) 0.66956(11) 0.1914(3) 0.0723(9) Uani 1 1 d . . . . .
C10 C 0.71793(10) 0.72377(10) 0.4126(3) 0.0700(8) Uani 1 1 d . . . . .
C5 C 0.73703(11) 0.82131(10) 0.3497(3) 0.0727(9) Uani 1 1 d . . . . .
C6 C 0.71823(13) 0.80314(11) 0.2391(3) 0.0833(11) Uani 1 1 d . . . . .
H6 H 0.7178 0.7819 0.2143 0.100 Uiso 1 1 calc R . . . .
C7 C 0.70044(12) 0.81617(10) 0.1667(3) 0.0806(10) Uani 1 1 d . . . . .
H7 H 0.6881 0.8037 0.0930 0.097 Uiso 1 1 calc R . . . .
C14 C 0.71242(11) 0.68410(12) 0.2391(4) 0.0809(10) Uani 1 1 d . . . . .
H14 H 0.6992 0.6695 0.1702 0.097 Uiso 1 1 calc R . . . .
C3 C 0.71963(11) 0.86640(10) 0.3102(3) 0.0757(9) Uani 1 1 d . . . . .
H3 H 0.7204 0.8878 0.3343 0.091 Uiso 1 1 calc R . . . .
C12 C 0.76412(11) 0.70742(11) 0.3773(3) 0.0762(9) Uani 1 1 d . . . . .
H12 H 0.7863 0.7095 0.4001 0.091 Uiso 1 1 calc R . . . .
C11 C 0.74986(11) 0.72502(11) 0.4491(3) 0.0792(10) Uani 1 1 d . . . . .
H11 H 0.7620 0.7378 0.5226 0.095 Uiso 1 1 calc R . . . .
C15 C 0.69932(10) 0.70270(11) 0.3071(4) 0.0777(9) Uani 1 1 d . . . . .
H15 H 0.6776 0.7012 0.2821 0.093 Uiso 1 1 calc R . . . .
C4 C 0.73759(11) 0.85286(10) 0.3828(4) 0.0768(9) Uani 1 1 d . . . . .
H4 H 0.7503 0.8655 0.4558 0.092 Uiso 1 1 calc R . . . .
C9 C 0.70293(11) 0.74429(10) 0.4834(4) 0.0743(9) Uani 1 1 d . . . . .
H9A H 0.6867 0.7475 0.4263 0.089 Uiso 1 1 calc R . . . .
H9B H 0.6886 0.7296 0.5555 0.089 Uiso 1 1 calc R . . . .
C17B C 0.5310(3) 0.4442(5) 0.5098(16) 0.064(3) Uani 0.5 1 d . . . A -1
C8 C 0.75566(11) 0.80618(11) 0.4339(4) 0.0780(9) Uani 1 1 d . . . . .
H8A H 0.7645 0.7936 0.3803 0.094 Uiso 1 1 calc R . . . .
H8B H 0.7764 0.8261 0.4761 0.094 Uiso 1 1 calc R . . . .
C19B C 0.7425(4) 0.5169(4) 0.1437(10) 0.179(2) Uani 0.5 1 d . . . A -1
H19B H 0.7402 0.5184 0.0553 0.215 Uiso 0.5 1 calc R . . A -1
C18B C 0.7626(3) 0.5484(3) 0.2155(13) 0.179(2) Uani 0.5 1 d G . . A -1
C23B C 0.7660(3) 0.5461(3) 0.3476(13) 0.179(2) Uani 0.5 1 d G . . A -1
H23B H 0.7794 0.5671 0.3957 0.215 Uiso 0.5 1 calc R . . A -1
C22B C 0.7493(4) 0.5124(3) 0.4079(10) 0.179(2) Uani 0.5 1 d G . . A -1
H22B H 0.7515 0.5109 0.4963 0.215 Uiso 0.5 1 calc R . . A -1
C21B C 0.7292(3) 0.4809(3) 0.3361(12) 0.179(2) Uani 0.5 1 d DG . . A -1
C20B C 0.7258(3) 0.4832(3) 0.2039(12) 0.179(2) Uani 0.5 1 d G . . A -1
H20B H 0.7123 0.4622 0.1559 0.215 Uiso 0.5 1 calc R . . A -1
N2 N 0.6775(4) 0.4428(6) 0.447(2) 0.264(12) Uani 0.5 1 d D . . A -1
H2 H 0.6740 0.4463 0.5260 0.317 Uiso 0.5 1 calc R . . A -1
C19A C 0.5664(4) 0.4157(4) 0.5275(12) 0.179(2) Uani 0.5 1 d . . . A -1
H19A H 0.5533 0.4019 0.5980 0.215 Uiso 0.5 1 calc R . . A -1
C18A C 0.5566(3) 0.4388(4) 0.4677(13) 0.179(2) Uani 0.5 1 d G . . A -1
C23A C 0.5763(3) 0.4594(3) 0.3624(12) 0.179(2) Uani 0.5 1 d G . . A -1
H23A H 0.5697 0.4749 0.3223 0.215 Uiso 0.5 1 calc R . . A -1
C22A C 0.6057(3) 0.4569(3) 0.3170(11) 0.179(2) Uani 0.5 1 d G . . A -1
H22A H 0.6189 0.4707 0.2466 0.215 Uiso 0.5 1 calc R . . A -1
C21A C 0.6155(3) 0.4338(4) 0.3769(13) 0.179(2) Uani 0.5 1 d DG . . A -1
C20A C 0.5959(4) 0.4132(3) 0.4821(13) 0.179(2) Uani 0.5 1 d G . . A -1
H20A H 0.6024 0.3978 0.5222 0.215 Uiso 0.5 1 calc R . . A -1
C24B C 0.7107(5) 0.4442(4) 0.3961(19) 0.179(2) Uani 0.5 1 d D . . A -1
H24A H 0.7049 0.4252 0.3331 0.215 Uiso 0.5 1 calc R . . A -1
H24B H 0.7252 0.4423 0.4642 0.215 Uiso 0.5 1 calc R . . A -1
C24A C 0.6527(4) 0.4348(5) 0.346(2) 0.179(2) Uani 0.5 1 d D . . A -1
H24C H 0.6467 0.4113 0.3113 0.215 Uiso 0.5 1 calc R . . A -1
H24D H 0.6649 0.4526 0.2788 0.215 Uiso 0.5 1 calc R . . A -1
C17A C 0.7777(6) 0.5898(4) 0.1442(19) 0.073(3) Uani 0.5 1 d . . . A -1


_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 O2 2.198(2) 6_565 ?
Zn1 O2 2.198(2) 12_655 ?
Zn1 O3 2.036(2) . ?
Zn1 O3 2.035(2) 13_665 ?
Zn1 O5 2.055(3) . ?
Zn1 O5 2.055(3) 13_665 ?
Zn2 O2 2.032(3) 12_655 ?
Zn2 O4 1.956(2) . ?
Zn2 O1 2.396(3) 12_655 ?
Zn2 O6 1.964(3) . ?
Zn2 N1 2.058(3) 6_564 ?
Zn2 C1 2.561(4) 12_655 ?
O2 Zn1 2.198(2) 8_654 ?
O2 Zn2 2.032(3) 11_565 ?
O2 C1 1.307(5) . ?
O4 C16 1.261(4) . ?
O3 C16 1.243(4) . ?
O1 Zn2 2.396(3) 11_565 ?
O1 C1 1.235(4) . ?
O6 C17A 1.18(2) . ?
O5 C17A 1.18(2) . ?
N1 Zn2 2.058(3) 8_655 ?
N1 H1 0.9800 . ?
N1 C9 1.493(5) . ?
N1 C8 1.485(4) . ?
C13 C16 1.501(4) . ?
C13 C14 1.385(5) . ?
C13 C12 1.378(5) . ?
C2 C1 1.482(5) . ?
C2 C7 1.388(5) . ?
C2 C3 1.388(5) . ?
C1 Zn2 2.561(4) 11_565 ?
C10 C11 1.384(5) . ?
C10 C15 1.386(5) . ?
C10 C9 1.505(4) . ?
C5 C6 1.393(5) . ?
C5 C4 1.373(5) . ?
C5 C8 1.522(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.365(6) . ?
C7 H7 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.369(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(5) . ?
C12 H12 0.9300 . ?
C12 C11 1.392(5) . ?
C11 H11 0.9300 . ?
C15 H15 0.9300 . ?
C4 H4 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C17B C18A 1.295(13) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C19B H19B 0.9300 . ?
C19B C18B 1.3900 . ?
C19B C20B 1.3900 . ?
C18B C23B 1.3900 . ?
C18B C17A 1.714(14) . ?
C23B H23B 0.9300 . ?
C23B C22B 1.3900 . ?
C22B H22B 0.9300 . ?
C22B C21B 1.3900 . ?
C21B C20B 1.3900 . ?
C21B C24B 1.489(13) . ?
C20B H20B 0.9300 . ?
N2 H2 0.8600 . ?
N2 C24B 1.478(15) . ?
N2 C24A 1.41(3) . ?
C19A H19A 0.9300 . ?
C19A C18A 1.3900 . ?
C19A C20A 1.3900 . ?
C18A C23A 1.3900 . ?
C23A H23A 0.9300 . ?
C23A C22A 1.3900 . ?
C22A H22A 0.9300 . ?
C22A C21A 1.3900 . ?
C21A C20A 1.3900 . ?
C21A C24A 1.590(14) . ?
C20A H20A 0.9300 . ?
C24B H24A 0.9700 . ?
C24B H24B 0.9700 . ?
C24A H24C 0.9700 . ?
C24A H24D 0.9700 . ?

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
O2 Zn1 O2 180.0 12_655 6_565 ?
O3 Zn1 O2 92.70(9) . 12_655 ?
O3 Zn1 O2 87.30(9) . 6_565 ?
O3 Zn1 O2 92.71(9) 13_665 6_565 ?
O3 Zn1 O2 87.30(9) 13_665 12_655 ?
O3 Zn1 O3 180.0 . 13_665 ?
O3 Zn1 O5 92.84(13) . . ?
O3 Zn1 O5 92.83(13) 13_665 13_665 ?
O3 Zn1 O5 87.17(13) 13_665 . ?
O3 Zn1 O5 87.16(13) . 13_665 ?
O5 Zn1 O2 91.80(11) 13_665 6_565 ?
O5 Zn1 O2 88.20(11) . 6_565 ?
O5 Zn1 O2 88.20(11) 13_665 12_655 ?
O5 Zn1 O2 91.80(11) . 12_655 ?
O5 Zn1 O5 180.0(3) 13_665 . ?
O2 Zn2 O1 58.79(10) 12_655 12_655 ?
O2 Zn2 N1 139.53(10) 12_655 6_564 ?
O2 Zn2 C1 30.38(11) 12_655 12_655 ?
O4 Zn2 O2 113.80(10) . 12_655 ?
O4 Zn2 O1 98.94(13) . 12_655 ?
O4 Zn2 O6 110.71(13) . . ?
O4 Zn2 N1 96.36(10) . 6_564 ?
O4 Zn2 C1 111.00(12) . 12_655 ?
O1 Zn2 C1 28.63(10) 12_655 12_655 ?
O6 Zn2 O2 96.04(12) . 12_655 ?
O6 Zn2 O1 147.55(12) . 12_655 ?
O6 Zn2 N1 97.78(12) . 6_564 ?
O6 Zn2 C1 122.59(13) . 12_655 ?
N1 Zn2 O1 91.57(11) 6_564 12_655 ?
N1 Zn2 C1 114.71(12) 6_564 12_655 ?
Zn2 O2 Zn1 100.75(10) 11_565 8_654 ?
C1 O2 Zn1 133.9(2) . 8_654 ?
C1 O2 Zn2 97.8(2) . 11_565 ?
C16 O4 Zn2 120.9(2) . . ?
C16 O3 Zn1 142.3(2) . . ?
C1 O1 Zn2 83.1(3) . 11_565 ?
C17A O6 Zn2 112.1(6) . . ?
C17A O5 Zn1 128.0(7) . . ?
Zn2 N1 H1 105.6 8_655 . ?
C9 N1 Zn2 108.8(2) . 8_655 ?
C9 N1 H1 105.6 . . ?
C8 N1 Zn2 115.3(2) . 8_655 ?
C8 N1 H1 105.6 . . ?
C8 N1 C9 115.0(3) . . ?
C14 C13 C16 121.2(3) . . ?
C12 C13 C16 119.3(3) . . ?
C12 C13 C14 119.5(3) . . ?
C7 C2 C1 121.7(3) . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 C7 118.8(3) . . ?
O2 C1 Zn2 51.82(18) . 11_565 ?
O2 C1 C2 119.0(3) . . ?
O1 C1 Zn2 68.3(2) . 11_565 ?
O1 C1 O2 119.5(4) . . ?
O1 C1 C2 121.3(4) . . ?
C2 C1 Zn2 164.4(3) . 11_565 ?
O4 C16 C13 117.2(3) . . ?
O3 C16 O4 125.7(3) . . ?
O3 C16 C13 117.0(3) . . ?
C11 C10 C15 118.2(3) . . ?
C11 C10 C9 122.3(3) . . ?
C15 C10 C9 119.4(3) . . ?
C6 C5 C8 121.1(3) . . ?
C4 C5 C6 118.3(3) . . ?
C4 C5 C8 120.6(4) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 H6 119.6 . . ?
C2 C7 H7 119.5 . . ?
C6 C7 C2 121.0(4) . . ?
C6 C7 H7 119.5 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
C13 C12 H12 120.2 . . ?
C13 C12 C11 119.7(3) . . ?
C11 C12 H12 120.2 . . ?
C10 C11 C12 120.9(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C10 C15 H15 119.5 . . ?
C14 C15 C10 121.1(3) . . ?
C14 C15 H15 119.5 . . ?
C5 C4 C3 121.6(4) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
N1 C9 C10 115.0(3) . . ?
N1 C9 H9A 108.5 . . ?
N1 C9 H9B 108.5 . . ?
C10 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
N1 C8 C5 112.1(3) . . ?
N1 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C5 C8 H8A 109.2 . . ?
C5 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C18B C19B H19B 120.0 . . ?
C18B C19B C20B 120.0 . . ?
C20B C19B H19B 120.0 . . ?
C19B C18B C17A 119.3(11) . . ?
C23B C18B C19B 120.0 . . ?
C23B C18B C17A 120.1(11) . . ?
C18B C23B H23B 120.0 . . ?
C18B C23B C22B 120.0 . . ?
C22B C23B H23B 120.0 . . ?
C23B C22B H22B 120.0 . . ?
C21B C22B C23B 120.0 . . ?
C21B C22B H22B 120.0 . . ?
C22B C21B C20B 120.0 . . ?
C22B C21B C24B 122.1(12) . . ?
C20B C21B C24B 117.9(12) . . ?
C19B C20B H20B 120.0 . . ?
C21B C20B C19B 120.0 . . ?
C21B C20B H20B 120.0 . . ?
C24B N2 H2 125.4 . . ?
C24A N2 H2 125.4 . . ?
C24A N2 C24B 109(2) . . ?
C18A C19A H19A 120.0 . . ?
C18A C19A C20A 120.0 . . ?
C20A C19A H19A 120.0 . . ?
C17B C18A C19A 123.2(11) . . ?
C17B C18A C23A 116.6(11) . . ?
C19A C18A C23A 120.0 . . ?
C18A C23A H23A 120.0 . . ?
C18A C23A C22A 120.0 . . ?
C22A C23A H23A 120.0 . . ?
C23A C22A H22A 120.0 . . ?
C21A C22A C23A 120.0 . . ?
C21A C22A H22A 120.0 . . ?
C22A C21A C20A 120.0 . . ?
C22A C21A C24A 122.4(9) . . ?
C20A C21A C24A 116.8(10) . . ?
C19A C20A H20A 120.0 . . ?
C21A C20A C19A 120.0 . . ?
C21A C20A H20A 120.0 . . ?
C21B C24B H24A 111.6 . . ?
C21B C24B H24B 111.6 . . ?
N2 C24B C21B 100.7(11) . . ?
N2 C24B H24A 111.6 . . ?
N2 C24B H24B 111.6 . . ?
H24A C24B H24B 109.4 . . ?
N2 C24A C21A 118.2(17) . . ?
N2 C24A H24C 107.8 . . ?
N2 C24A H24D 107.8 . . ?
C21A C24A H24C 107.8 . . ?
C21A C24A H24D 107.8 . . ?
H24C C24A H24D 107.1 . . ?
O6 C17A C18B 106.0(14) . . ?
O5 C17A O6 145.1(12) . . ?
O5 C17A C18B 109.0(12) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method ?
_olex2_submission_special_instructions 'No special instructions were received'
