# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_K2L1
_database_code_depnum_ccdc_archive 'CCDC 1040481'
_audit_update_record             
;
2014-12-22 deposited with the CCDC.
2015-01-20 downloaded from the CCDC.
;
_audit_creation_date             2014-09-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H24 K2 N2 O6'
_chemical_formula_sum            'C20 H24 K2 N2 O6'
_chemical_formula_weight         466.61
_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'
K K 0.2009 0.2494 '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'

_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                   19.637(2)
_cell_length_b                   9.4274(10)
_cell_length_c                   5.7239(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.912(3)
_cell_angle_gamma                90.00
_cell_volume                     1057.16(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1094
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.11
_cell_measurement_theta_min      4.16
_exptl_absorpt_coefficient_mu    0.488
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0665 before and 0.0570 after correction.
The Ratio of minimum to maximum transmission is 0.9202.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0857
_diffrn_reflns_av_unetI/netI     0.1004
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            10874
_diffrn_reflns_theta_full        28.50
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.40
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_number_gt                1730
_reflns_number_total             2790
_reflns_threshold_expression     >2sigma(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  'XLMP (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         2790
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1078
_refine_ls_R_factor_gt           0.0510
_refine_ls_restrained_S_all      1.014
_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)+(0.0402P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.1115
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O15-H15A
 0.84 with sigma of 0.02
 O15-H15B
 0.84 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10)
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
K1 K 0.52248(3) 0.88192(6) 0.26448(10) 0.01625(16) Uani 1 d . . .
O2 O 0.57490(9) 0.62162(19) 0.2797(3) 0.0190(4) Uani 1 d . . .
C3 C 0.62037(13) 0.5346(3) 0.3524(5) 0.0142(6) Uani 1 d . . .
O4 O 0.61313(9) 0.45031(19) 0.5214(3) 0.0195(5) Uani 1 d . . .
C5 C 0.68583(13) 0.5269(3) 0.2288(4) 0.0127(5) Uani 1 d . . .
C6 C 0.69478(13) 0.6138(3) 0.0370(4) 0.0157(5) Uani 1 d . . .
H6 H 0.6609 0.6821 -0.0096 0.019 Uiso 1 calc . . R
C7 C 0.75288(13) 0.6015(3) -0.0867(5) 0.0176(6) Uani 1 d . . .
H7 H 0.7582 0.6613 -0.2177 0.021 Uiso 1 calc . . R
C8 C 0.80332(14) 0.5031(3) -0.0222(5) 0.0182(6) Uani 1 d . . .
C9 C 0.79514(14) 0.4189(3) 0.1749(5) 0.0209(6) Uani 1 d . . .
H9 H 0.8297 0.3529 0.2246 0.025 Uiso 1 calc . . R
C10 C 0.73693(13) 0.4307(3) 0.2990(5) 0.0183(6) Uani 1 d . . .
H10 H 0.7320 0.3727 0.4325 0.022 Uiso 1 calc . . R
C11 C 0.86288(13) 0.4843(3) -0.1719(5) 0.0226(7) Uani 1 d . . .
H11A H 0.8534 0.4023 -0.2772 0.027 Uiso 1 calc . . R
H11B H 0.8663 0.5695 -0.2715 0.027 Uiso 1 calc . . R
N12 N 0.92848(11) 0.4618(2) -0.0428(4) 0.0182(5) Uani 1 d . . .
C13 C 0.94985(14) 0.5897(3) 0.0872(5) 0.0229(7) Uani 1 d . . .
H13A H 0.9166 0.6110 0.2047 0.028 Uiso 1 calc . . R
H13B H 0.9506 0.6710 -0.0220 0.028 Uiso 1 calc . . R
C14 C 0.97974(14) 0.4299(3) -0.2098(5) 0.0248(7) Uani 1 d . . .
H14A H 0.9812 0.5083 -0.3244 0.030 Uiso 1 calc . . R
H14B H 0.9665 0.3423 -0.2968 0.030 Uiso 1 calc . . R
O15 O 0.42333(10) 0.8278(2) 0.5665(3) 0.0186(4) Uani 1 d . . D
H15A H 0.4002(13) 0.752(2) 0.543(5) 0.028 Uiso 1 d . . DR
H15B H 0.4016(14) 0.862(3) 0.680(4) 0.028 Uiso 1 d . . DR


_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
K1 K1 3.6510(11) 3_676 ?
K1 O2 3.0248(19) 4_575 ?
K1 O2 3.057(2) 4_576 ?
K1 O2 2.9599(19) 2_655 ?
K1 O2 2.6603(18) . ?
K1 C3 3.183(3) 2_655 ?
K1 C3 3.240(3) 4_575 ?
K1 O4 3.097(2) 2_655 ?
K1 O4 2.8184(18) 4_575 ?
K1 O15 2.947(2) 4_575 ?
K1 O15 3.069(2) 3_676 ?
K1 O15 2.7384(19) . ?
O2 K1 3.0249(19) 4_576 ?
O2 K1 3.057(2) 4_575 ?
O2 K1 2.9599(19) 2_645 ?
O2 C3 1.262(3) . ?
C3 K1 3.240(3) 4_576 ?
C3 K1 3.183(3) 2_645 ?
C3 O4 1.268(3) . ?
C3 C5 1.511(3) . ?
O4 K1 2.8185(18) 4_576 ?
O4 K1 3.097(2) 2_645 ?
C5 C6 1.391(3) . ?
C5 C10 1.391(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.388(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.389(4) . ?
C8 C9 1.397(4) . ?
C8 C11 1.507(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.391(4) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 N12 1.456(3) . ?
N12 C13 1.463(3) . ?
N12 C14 1.466(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.519(4) 3_765 ?
C14 C13 1.519(4) 3_765 ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
O15 K1 2.947(2) 4_576 ?
O15 K1 3.069(2) 3_676 ?
O15 H15A 0.851(17) . ?
O15 H15B 0.864(17) . ?

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 K1 K1 53.86(4) 2_655 3_676 ?
O2 K1 K1 130.60(5) . 3_676 ?
O2 K1 K1 51.44(4) 4_576 3_676 ?
O2 K1 K1 143.01(4) 4_575 3_676 ?
O2 K1 O2 140.50(7) 4_575 4_576 ?
O2 K1 O2 100.85(5) 2_655 4_575 ?
O2 K1 O2 81.62(6) . 4_576 ?
O2 K1 O2 162.43(4) . 2_655 ?
O2 K1 O2 82.23(6) . 4_575 ?
O2 K1 O2 105.30(5) 2_655 4_576 ?
O2 K1 C3 99.46(6) 2_655 4_575 ?
O2 K1 C3 90.02(6) . 4_575 ?
O2 K1 C3 99.34(6) 4_575 2_655 ?
O2 K1 C3 22.91(6) 4_575 4_575 ?
O2 K1 C3 23.34(6) 2_655 2_655 ?
O2 K1 C3 121.84(6) 4_576 4_575 ?
O2 K1 C3 116.21(6) 4_576 2_655 ?
O2 K1 C3 139.25(6) . 2_655 ?
O2 K1 O4 106.13(6) . 4_575 ?
O2 K1 O4 137.13(5) 4_576 2_655 ?
O2 K1 O4 121.75(6) . 2_655 ?
O2 K1 O4 43.00(5) 2_655 2_655 ?
O2 K1 O4 81.47(5) 4_575 2_655 ?
O2 K1 O15 99.59(5) 4_575 3_676 ?
O2 K1 O15 63.53(5) 2_655 3_676 ?
O2 K1 O15 68.76(5) . 4_575 ?
O2 K1 O15 133.41(6) . 3_676 ?
O2 K1 O15 95.60(6) . . ?
O2 K1 O15 67.60(5) 4_576 3_676 ?
C3 K1 K1 68.00(5) 2_655 3_676 ?
C3 K1 K1 125.10(5) 4_575 3_676 ?
C3 K1 C3 107.17(6) 2_655 4_575 ?
O4 K1 K1 91.19(4) 2_655 3_676 ?
O4 K1 K1 102.42(4) 4_575 3_676 ?
O4 K1 O2 87.45(5) 4_575 2_655 ?
O4 K1 O2 44.56(5) 4_575 4_575 ?
O4 K1 O2 107.45(5) 4_575 4_576 ?
O4 K1 C3 23.24(6) 2_655 2_655 ?
O4 K1 C3 95.52(6) 2_655 4_575 ?
O4 K1 C3 22.82(6) 4_575 4_575 ?
O4 K1 C3 102.68(6) 4_575 2_655 ?
O4 K1 O4 99.88(5) 4_575 2_655 ?
O4 K1 O15 55.81(5) 4_575 3_676 ?
O4 K1 O15 127.56(6) 4_575 4_575 ?
O15 K1 K1 47.12(4) 3_676 3_676 ?
O15 K1 K1 55.20(4) . 3_676 ?
O15 K1 K1 120.43(4) 4_575 3_676 ?
O15 K1 O2 94.20(5) 4_575 2_655 ?
O15 K1 O2 73.34(5) . 2_655 ?
O15 K1 O2 84.09(5) 4_575 4_575 ?
O15 K1 O2 122.27(5) 4_575 4_576 ?
O15 K1 O2 66.17(5) . 4_576 ?
O15 K1 O2 151.42(6) . 4_575 ?
O15 K1 C3 70.91(6) 4_575 2_655 ?
O15 K1 C3 170.96(7) . 4_575 ?
O15 K1 C3 78.63(6) 3_676 4_575 ?
O15 K1 C3 86.82(6) 3_676 2_655 ?
O15 K1 C3 64.07(6) . 2_655 ?
O15 K1 C3 106.99(6) 4_575 4_575 ?
O15 K1 O4 75.50(5) . 2_655 ?
O15 K1 O4 104.36(5) 3_676 2_655 ?
O15 K1 O4 156.40(6) . 4_575 ?
O15 K1 O4 54.17(5) 4_575 2_655 ?
O15 K1 O15 68.79(5) . 4_575 ?
O15 K1 O15 102.32(5) . 3_676 ?
O15 K1 O15 157.73(5) 4_575 3_676 ?
K1 O2 K1 74.70(5) 2_645 4_575 ?
K1 O2 K1 117.08(6) . 2_645 ?
K1 O2 K1 83.40(5) . 4_576 ?
K1 O2 K1 82.78(5) . 4_575 ?
K1 O2 K1 79.15(5) 2_645 4_576 ?
K1 O2 K1 140.50(7) 4_576 4_575 ?
C3 O2 K1 119.69(15) . 4_575 ?
C3 O2 K1 88.15(15) . 4_576 ?
C3 O2 K1 88.31(15) . 2_645 ?
C3 O2 K1 150.90(17) . . ?
K1 C3 K1 72.83(6) 2_645 4_576 ?
O2 C3 K1 68.35(14) . 2_645 ?
O2 C3 K1 68.94(13) . 4_576 ?
O2 C3 O4 123.1(2) . . ?
O2 C3 C5 118.8(2) . . ?
O4 C3 K1 59.58(13) . 4_576 ?
O4 C3 K1 74.55(14) . 2_645 ?
O4 C3 C5 118.1(2) . . ?
C5 C3 K1 156.75(17) . 4_576 ?
C5 C3 K1 130.19(16) . 2_645 ?
K1 O4 K1 80.12(5) 4_576 2_645 ?
C3 O4 K1 82.21(15) . 2_645 ?
C3 O4 K1 97.60(15) . 4_576 ?
C6 C5 C3 119.9(2) . . ?
C6 C5 C10 119.0(2) . . ?
C10 C5 C3 121.1(2) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.4 . . ?
C6 C7 C8 121.1(2) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 C9 118.3(2) . . ?
C7 C8 C11 119.6(2) . . ?
C9 C8 C11 121.9(3) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9 119.6 . . ?
C5 C10 H10 119.8 . . ?
C9 C10 C5 120.4(2) . . ?
C9 C10 H10 119.8 . . ?
C8 C11 H11A 108.5 . . ?
C8 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
N12 C11 C8 115.0(2) . . ?
N12 C11 H11A 108.5 . . ?
N12 C11 H11B 108.5 . . ?
C11 N12 C13 110.6(2) . . ?
C11 N12 C14 108.8(2) . . ?
C13 N12 C14 108.4(2) . . ?
N12 C13 H13A 109.5 . . ?
N12 C13 H13B 109.5 . . ?
N12 C13 C14 110.8(2) . 3_765 ?
H13A C13 H13B 108.1 . . ?
C14 C13 H13A 109.5 3_765 . ?
C14 C13 H13B 109.5 3_765 . ?
N12 C14 C13 111.6(2) . 3_765 ?
N12 C14 H14A 109.3 . . ?
N12 C14 H14B 109.3 . . ?
C13 C14 H14A 109.3 3_765 . ?
C13 C14 H14B 109.3 3_765 . ?
H14A C14 H14B 108.0 . . ?
K1 O15 K1 77.68(5) . 3_676 ?
K1 O15 K1 83.59(6) . 4_576 ?
K1 O15 K1 105.74(6) 4_576 3_676 ?
K1 O15 H15A 117.0(19) . . ?
K1 O15 H15A 80(2) 4_576 . ?
K1 O15 H15A 165(2) 3_676 . ?
K1 O15 H15B 67(2) 3_676 . ?
K1 O15 H15B 145(2) . . ?
K1 O15 H15B 108(2) 4_576 . ?
H15A O15 H15B 98(3) . . ?

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
O15 H15A O4 0.851(17) 1.96(2) 2.755(3) 155(3) 3_666
O15 H15B O4 0.863(17) 1.940(19) 2.764(3) 159(3) 2_656


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
K1 K1 O2 K1 93.82(8) 3_676 . . 2_645 ?
K1 K1 O2 K1 19.61(7) 3_676 . . 4_576 ?
K1 K1 O2 K1 162.51(3) 3_676 . . 4_575 ?
K1 K1 O2 C3 -54.4(3) 3_676 . . . ?
K1 K1 O15 K1 -107.70(5) 3_676 . . 4_576 ?
K1 O2 C3 K1 152.1(3) . . . 2_645 ?
K1 O2 C3 K1 -79.19(4) 2_645 . . 4_576 ?
K1 O2 C3 K1 -150.48(13) 4_575 . . 4_576 ?
K1 O2 C3 K1 -71.29(11) 4_575 . . 2_645 ?
K1 O2 C3 K1 79.19(4) 4_576 . . 2_645 ?
K1 O2 C3 K1 72.9(3) . . . 4_576 ?
K1 O2 C3 O4 -124.4(2) 4_575 . . . ?
K1 O2 C3 O4 26.1(2) 4_576 . . . ?
K1 O2 C3 O4 -53.1(2) 2_645 . . . ?
K1 O2 C3 O4 99.0(4) . . . . ?
K1 O2 C3 C5 125.0(2) 2_645 . . . ?
K1 O2 C3 C5 -155.8(2) 4_576 . . . ?
K1 O2 C3 C5 -82.9(4) . . . . ?
K1 O2 C3 C5 53.7(3) 4_575 . . . ?
K1 C3 O4 K1 78.88(6) 4_576 . . 2_645 ?
K1 C3 O4 K1 -78.88(6) 2_645 . . 4_576 ?
K1 C3 C5 C6 -104.7(5) 4_576 . . . ?
K1 C3 C5 C6 84.4(3) 2_645 . . . ?
K1 C3 C5 C10 -93.6(3) 2_645 . . . ?
K1 C3 C5 C10 77.3(5) 4_576 . . . ?
O2 K1 O2 K1 -105.31(6) 4_575 . . 2_645 ?
O2 K1 O2 K1 179.54(3) 4_576 . . 4_575 ?
O2 K1 O2 K1 -3.86(10) 2_655 . . 2_645 ?
O2 K1 O2 K1 110.85(6) 4_576 . . 2_645 ?
O2 K1 O2 K1 -179.53(3) 4_575 . . 4_576 ?
O2 K1 O2 K1 -36.63(5) 4_575 . . 4_575 ?
O2 K1 O2 K1 36.64(5) 4_576 . . 4_576 ?
O2 K1 O2 K1 64.82(9) 2_655 . . 4_575 ?
O2 K1 O2 K1 -78.08(9) 2_655 . . 4_576 ?
O2 K1 O2 C3 -152.1(3) 2_655 . . . ?
O2 K1 O2 C3 -37.4(3) 4_576 . . . ?
O2 K1 O2 C3 106.4(3) 4_575 . . . ?
O2 K1 O15 K1 113.06(12) 4_575 . . 4_576 ?
O2 K1 O15 K1 -49.23(5) 4_576 . . 4_576 ?
O2 K1 O15 K1 58.47(5) 4_576 . . 3_676 ?
O2 K1 O15 K1 -57.20(5) 2_655 . . 3_676 ?
O2 K1 O15 K1 -164.90(6) 2_655 . . 4_576 ?
O2 K1 O15 K1 136.74(5) . . . 3_676 ?
O2 K1 O15 K1 29.04(6) . . . 4_576 ?
O2 K1 O15 K1 -139.24(11) 4_575 . . 3_676 ?
O2 C3 O4 K1 -28.4(3) . . . 4_576 ?
O2 C3 O4 K1 50.4(2) . . . 2_645 ?
O2 C3 C5 C6 -0.6(4) . . . . ?
O2 C3 C5 C10 -178.6(2) . . . . ?
C3 K1 O2 K1 -10.01(13) 2_655 . . 2_645 ?
C3 K1 O2 K1 -84.22(10) 2_655 . . 4_576 ?
C3 K1 O2 K1 158.86(6) 4_575 . . 4_576 ?
C3 K1 O2 K1 -126.92(8) 4_575 . . 2_645 ?
C3 K1 O2 K1 -58.24(6) 4_575 . . 4_575 ?
C3 K1 O2 K1 58.68(10) 2_655 . . 4_575 ?
C3 K1 O2 C3 -158.3(3) 2_655 . . . ?
C3 K1 O2 C3 84.8(3) 4_575 . . . ?
C3 K1 O15 K1 172.04(8) 2_655 . . 4_576 ?
C3 K1 O15 K1 -95.0(4) 4_575 . . 3_676 ?
C3 K1 O15 K1 157.3(4) 4_575 . . 4_576 ?
C3 K1 O15 K1 -80.26(6) 2_655 . . 3_676 ?
C3 C5 C6 C7 -176.0(2) . . . . ?
C3 C5 C10 C9 176.2(2) . . . . ?
O4 K1 O2 K1 142.48(5) 4_575 . . 4_576 ?
O4 K1 O2 K1 -143.31(7) 4_575 . . 2_645 ?
O4 K1 O2 K1 -30.41(9) 2_655 . . 2_645 ?
O4 K1 O2 K1 38.27(7) 2_655 . . 4_575 ?
O4 K1 O2 K1 -74.62(6) 4_575 . . 4_575 ?
O4 K1 O2 K1 -104.63(5) 2_655 . . 4_576 ?
O4 K1 O2 C3 68.4(3) 4_575 . . . ?
O4 K1 O2 C3 -178.7(3) 2_655 . . . ?
O4 K1 O15 K1 150.42(6) 2_655 . . 4_576 ?
O4 K1 O15 K1 -128.16(14) 4_575 . . 4_576 ?
O4 K1 O15 K1 -20.46(16) 4_575 . . 3_676 ?
O4 K1 O15 K1 -101.88(5) 2_655 . . 3_676 ?
O4 C3 C5 C6 177.6(2) . . . . ?
O4 C3 C5 C10 -0.4(4) . . . . ?
C5 C3 O4 K1 -127.7(2) . . . 2_645 ?
C5 C3 O4 K1 153.43(19) . . . 4_576 ?
C5 C6 C7 C8 -0.2(4) . . . . ?
C6 C5 C10 C9 -1.9(4) . . . . ?
C6 C7 C8 C9 -1.7(4) . . . . ?
C6 C7 C8 C11 175.0(3) . . . . ?
C7 C8 C9 C10 1.9(4) . . . . ?
C7 C8 C11 N12 141.1(3) . . . . ?
C8 C9 C10 C5 -0.1(4) . . . . ?
C8 C11 N12 C13 -67.3(3) . . . . ?
C8 C11 N12 C14 173.9(2) . . . . ?
C9 C8 C11 N12 -42.3(4) . . . . ?
C10 C5 C6 C7 2.0(4) . . . . ?
C11 C8 C9 C10 -174.8(3) . . . . ?
C11 N12 C13 C14 -176.4(2) . . . 3_765 ?
C11 N12 C14 C13 178.0(2) . . . 3_765 ?
C13 N12 C14 C13 57.7(3) . . . 3_765 ?
C14 N12 C13 C14 -57.3(3) . . . 3_765 ?
O15 K1 O2 K1 84.59(7) 3_676 . . 4_576 ?
O15 K1 O2 K1 158.81(6) 3_676 . . 2_645 ?
O15 K1 O2 K1 -132.51(6) 3_676 . . 4_575 ?
O15 K1 O2 K1 -92.88(5) 4_575 . . 4_576 ?
O15 K1 O2 K1 114.67(5) . . . 4_575 ?
O15 K1 O2 K1 -18.66(6) 4_575 . . 2_645 ?
O15 K1 O2 K1 50.02(5) 4_575 . . 4_575 ?
O15 K1 O2 K1 45.99(8) . . . 2_645 ?
O15 K1 O2 K1 -28.23(6) . . . 4_576 ?
O15 K1 O2 C3 -102.3(3) . . . . ?
O15 K1 O2 C3 10.5(4) 3_676 . . . ?
O15 K1 O2 C3 -166.9(3) 4_575 . . . ?
O15 K1 O15 K1 0.0 3_676 . . 3_676 ?
O15 K1 O15 K1 -107.70(5) 3_676 . . 4_576 ?
O15 K1 O15 K1 93.66(8) 4_575 . . 4_576 ?
O15 K1 O15 K1 -158.64(6) 4_575 . . 3_676 ?

_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_H2L1
_database_code_depnum_ccdc_archive 'CCDC 1040482'
_audit_update_record             
;
2014-12-22 deposited with the CCDC.
2015-01-20 downloaded from the CCDC.
;
_audit_creation_date             2014-09-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H22 N2 O4'
_chemical_formula_sum            'C20 H22 N2 O4'
_chemical_formula_weight         354.40
_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'
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'

_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                   6.0077(9)
_cell_length_b                   16.128(3)
_cell_length_c                   9.1598(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.630(5)
_cell_angle_gamma                90.00
_cell_volume                     858.7(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    540
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      23.56
_cell_measurement_theta_min      2.62
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0750 before and 0.0617 after correction.
The Ratio of minimum to maximum transmission is 0.9112.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0811
_diffrn_reflns_av_unetI/netI     0.0924
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8237
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.53
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_number_gt                1286
_reflns_number_total             2282
_reflns_threshold_expression     >2sigma(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  'XLMP (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         2282
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1174
_refine_ls_R_factor_gt           0.0595
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0616P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1533
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H5 of C5, H6 of C6, H8 of C8, H9 of C9
 At 1.5 times of:
  H1 of C13
2. Restrained distances
 H1-O1
 0.84 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9)
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.4241(2) 0.40318(10) 0.18934(17) 0.0243(4) Uani 1 d . . D
C2 C 0.3691(3) 0.36173(14) 0.2978(2) 0.0207(5) Uani 1 d . . .
O3 O 0.1821(3) 0.32950(10) 0.28609(18) 0.0325(5) Uani 1 d . . .
C4 C 0.5556(3) 0.35634(13) 0.4415(2) 0.0175(5) Uani 1 d . . .
C5 C 0.7717(3) 0.39018(14) 0.4523(2) 0.0206(5) Uani 1 d . . .
H5 H 0.8045 0.4165 0.3673 0.025 Uiso 1 calc . . R
C6 C 0.9396(4) 0.38551(14) 0.5874(2) 0.0223(5) Uani 1 d . . .
H6 H 1.0873 0.4084 0.5934 0.027 Uiso 1 calc . . R
C7 C 0.8969(3) 0.34828(13) 0.7136(2) 0.0184(5) Uani 1 d . . .
C8 C 0.6824(4) 0.31224(13) 0.7005(2) 0.0231(5) Uani 1 d . . .
H8 H 0.6515 0.2844 0.7847 0.028 Uiso 1 calc . . R
C9 C 0.5128(4) 0.31641(14) 0.5658(2) 0.0229(5) Uani 1 d . . .
H9 H 0.3668 0.2918 0.5587 0.027 Uiso 1 calc . . R
C10 C 1.0759(4) 0.34649(13) 0.8629(2) 0.0201(5) Uani 1 d . . .
H10A H 1.0498 0.2967 0.9195 0.024 Uiso 1 calc . . R
H10B H 1.2297 0.3410 0.8430 0.024 Uiso 1 calc . . R
N11 N 1.0767(3) 0.42072(11) 0.95941(19) 0.0177(4) Uani 1 d . . .
C12 C 0.8593(3) 0.42923(14) 1.0066(2) 0.0193(5) Uani 1 d . . .
H12A H 0.8290 0.3777 1.0571 0.023 Uiso 1 calc . . R
H12B H 0.7296 0.4382 0.9169 0.023 Uiso 1 calc . . R
C13 C 1.1227(4) 0.49834(13) 0.8864(2) 0.0193(5) Uani 1 d . . .
H13A H 0.9969 0.5086 0.7950 0.023 Uiso 1 calc . . R
H13B H 1.2680 0.4928 0.8550 0.023 Uiso 1 calc . . R
H1 H 0.296(3) 0.4064(14) 0.111(2) 0.029 Uiso 1 d . . DR


_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
O1 C2 1.307(3) . ?
O1 H1 0.914(16) . ?
C2 O3 1.218(2) . ?
C2 C4 1.500(3) . ?
C4 C5 1.388(3) . ?
C4 C9 1.387(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.382(3) . ?
C7 C8 1.391(3) . ?
C7 C10 1.511(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.389(3) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 N11 1.488(3) . ?
N11 C12 1.483(3) . ?
N11 C13 1.478(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.511(3) 3_767 ?
C13 C12 1.511(3) 3_767 ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?

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
C2 O1 H1 107.5(15) . . ?
O1 C2 C4 114.85(18) . . ?
O3 C2 O1 123.78(19) . . ?
O3 C2 C4 121.4(2) . . ?
C5 C4 C2 121.16(19) . . ?
C9 C4 C2 119.65(18) . . ?
C9 C4 C5 119.19(18) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.9(2) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.5(2) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C8 118.22(18) . . ?
C6 C7 C10 121.65(19) . . ?
C8 C7 C10 120.1(2) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.8(2) . . ?
C9 C8 H8 119.6 . . ?
C4 C9 C8 120.3(2) . . ?
C4 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C7 C10 H10A 108.6 . . ?
C7 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
N11 C10 C7 114.66(16) . . ?
N11 C10 H10A 108.6 . . ?
N11 C10 H10B 108.6 . . ?
C12 N11 C10 112.15(16) . . ?
C13 N11 C10 112.69(16) . . ?
C13 N11 C12 109.43(16) . . ?
N11 C12 H12A 109.7 . . ?
N11 C12 H12B 109.7 . . ?
N11 C12 C13 109.66(16) . 3_767 ?
H12A C12 H12B 108.2 . . ?
C13 C12 H12A 109.7 3_767 . ?
C13 C12 H12B 109.7 3_767 . ?
N11 C13 C12 110.65(17) . 3_767 ?
N11 C13 H13A 109.5 . . ?
N11 C13 H13B 109.5 . . ?
C12 C13 H13A 109.5 3_767 . ?
C12 C13 H13B 109.5 3_767 . ?
H13A C13 H13B 108.1 . . ?

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
O1 H1 N11 0.914(16) 1.668(17) 2.579(2) 173(2) 1_454

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
O1 C2 C4 C5 -2.8(3) . . . . ?
O1 C2 C4 C9 177.6(2) . . . . ?
C2 C4 C5 C6 178.9(2) . . . . ?
C2 C4 C9 C8 -178.80(19) . . . . ?
O3 C2 C4 C5 177.3(2) . . . . ?
O3 C2 C4 C9 -2.3(3) . . . . ?
C4 C5 C6 C7 -0.6(3) . . . . ?
C5 C4 C9 C8 1.6(3) . . . . ?
C5 C6 C7 C8 2.5(3) . . . . ?
C5 C6 C7 C10 -177.2(2) . . . . ?
C6 C7 C8 C9 -2.4(3) . . . . ?
C6 C7 C10 N11 86.7(3) . . . . ?
C7 C8 C9 C4 0.4(3) . . . . ?
C7 C10 N11 C12 63.7(2) . . . . ?
C7 C10 N11 C13 -60.3(2) . . . . ?
C8 C7 C10 N11 -93.1(2) . . . . ?
C9 C4 C5 C6 -1.6(3) . . . . ?
C10 C7 C8 C9 177.29(19) . . . . ?
C10 N11 C12 C13 175.73(16) . . . 3_767 ?
C10 N11 C13 C12 -175.44(16) . . . 3_767 ?
C12 N11 C13 C12 59.1(2) . . . 3_767 ?
C13 N11 C12 C13 -58.5(2) . . . 3_767 ?

_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_1
_database_code_depnum_ccdc_archive 'CCDC 1040483'
_audit_update_record             
;
2014-12-22 deposited with the CCDC.
2015-01-20 downloaded from the CCDC.
;
_audit_creation_date             2014-09-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C40 H42 N4 O10 Zn3, C6 H14 N2 O2'
_chemical_formula_sum            'C46 H56 N6 O12 Zn3'
_chemical_formula_weight         1081.08
_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'
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 0.2910 1.4260 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z'
5 '-x, -y, -z'
6 'x, -y, z'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z'

_cell_length_a                   17.666(7)
_cell_length_b                   24.302(6)
_cell_length_c                   6.0130(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.76(4)
_cell_angle_gamma                90.00
_cell_volume                     2536.1(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    13301
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.88
_cell_measurement_theta_min      2.88
_exptl_absorpt_coefficient_mu    1.471
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   'XScale within XDS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.1644
_diffrn_reflns_av_unetI/netI     0.0798
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            23326
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.89
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'Phi Scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.71090
_diffrn_source                   'Australian Synchrotron'
_diffrn_standards_number         0
_reflns_number_gt                2682
_reflns_number_total             3438
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'BluIce (McPhillips, 2002)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_refine_diff_density_max         1.674
_refine_diff_density_min         -1.173
_refine_diff_density_rms         0.150
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3438
_refine_ls_number_restraints     43
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0639
_refine_ls_restrained_S_all      1.010
_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)+(0.1222P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1661
_refine_ls_wR_factor_ref         0.1758
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H12A of C12A, H9 of C9, H18 of C18, H8 of C8, H11A of
  C11A, H8A of C8A, H11 of C11, H9A of C9A, H12 of C12
 At 1.5 times of:
  All C(H,H,H) groups, H3 of C9
2. Restrained distances
 O3-H3
 0.84 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C12) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C5) \\sim Ueq: with sigma of
0.001 and sigma for terminal atoms of 0.02
Uanis(C9A) \\sim Ueq, Uanis(C8A) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C9)
\\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4. Others
 Fixed Sof: O4(0.5) C9A(0.5) H9A(0.5) C11(0.5) H11(0.5) C12(0.5) H12(0.5)
 C8A(0.5) H8A(0.5) C21(0.5) H21A(0.5) H21B(0.5) H21C(0.5) O4A(0.5) C20(0.5)
 H20A(0.5) H20B(0.5) H20C(0.5) C12A(0.5) H12A(0.5) C11A(0.5) H11A(0.5) C8(0.5)
 H8(0.5) C9(0.5) H9(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16A,H16B), C15(H15A,H15B)
5.b Aromatic/amide H refined with riding coordinates:
 C9A(H9A), C11(H11), C12(H12), C8A(H8A), C18(H18), C12A(H12A), C11A(H11A),
 C8(H8), C9(H9)
5.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Zn1 Zn 0.5000 0.0000 1.0000 0.0219(2) Uani 1 d . . 4 S T P
Zn2 Zn 0.5000 0.059738(18) 0.5000 0.02385(19) Uani 1 d . . 2 S T P
O3 O 0.54449(19) 0.0000 0.7111(5) 0.0230(6) Uani 1 d . . 2 DS T P
O4 O 0.4390(3) 0.0753(2) 0.9447(8) 0.0321(11) Uani 0.50 d A 2 1 . . .
O6 O 0.42160(15) 0.10418(9) 0.5923(4) 0.0316(5) Uani 1 d A . 1 . . .
N14 N 0.07178(19) 0.22480(14) 0.6509(6) 0.0401(7) Uani 1 d . . 1 . . .
C13 C 0.1258(2) 0.22303(19) 0.8671(8) 0.0456(10) Uani 1 d B . 1 . . .
H13A H 0.0998 0.2073 0.9848 0.055 Uiso 1 calc . . 1 R . .
H13B H 0.1424 0.2609 0.9136 0.055 Uiso 1 calc . . 1 R . .
C9A C 0.2349(5) 0.1990(4) 0.6794(15) 0.0285(18) Uani 0.50 d B 1 1 . U .
H9A H 0.2170 0.2277 0.5752 0.034 Uiso 0.50 calc B 1 1 R . .
C11 C 0.2375(6) 0.1624(4) 1.0248(18) 0.035(2) Uani 0.50 d B 2 1 . U .
H11 H 0.2208 0.1633 1.1661 0.042 Uiso 0.50 calc B 2 1 R . .
C12 C 0.3052(6) 0.1339(4) 1.0092(17) 0.036(2) Uani 0.50 d B 2 1 . U .
H12 H 0.3361 0.1184 1.1407 0.043 Uiso 0.50 calc B 2 1 R . .
C16 C 0.0249(2) 0.17526(17) 0.6153(8) 0.0428(9) Uani 1 d . . 1 . . .
H16A H -0.0079 0.1731 0.7316 0.051 Uiso 1 calc . . 1 R . .
H16B H 0.0589 0.1425 0.6318 0.051 Uiso 1 calc . . 1 R . .
C8A C 0.2994(5) 0.1701(3) 0.6529(14) 0.0249(17) Uani 0.50 d B 1 1 . U .
H8A H 0.3252 0.1792 0.5326 0.030 Uiso 0.50 calc B 1 1 R . .
C7 C 0.3269(2) 0.12836(18) 0.7979(6) 0.0385(8) Uani 1 d . . 1 . . .
C15 C 0.0232(2) 0.27362(16) 0.6175(7) 0.0413(9) Uani 1 d . . 1 . . .
H15A H 0.0558 0.3071 0.6413 0.050 Uiso 1 calc . . 1 R . .
H15B H -0.0116 0.2740 0.7288 0.050 Uiso 1 calc . . 1 R . .
C10 C 0.1957(2) 0.18844(17) 0.8481(7) 0.0406(8) Uani 1 d . . 1 . . .
C5 C 0.3942(3) 0.09515(18) 0.7639(7) 0.0423(8) Uani 1 d A . 1 . U .
O17 O 0.2973(3) 0.0000 0.2750(9) 0.0804(19) Uani 1 d . . 2 S T P
N19 N 0.2064(4) 0.0000 0.4923(13) 0.084(2) Uani 1 d . . 2 S T P
C18 C 0.2736(4) 0.0000 0.4365(13) 0.0567(17) Uani 1 d C . 2 S T P
H18 H 0.3137 0.0000 0.5661 0.068 Uiso 1 calc . . 2 RS T P
C21 C 0.1570(9) 0.0482(8) 0.368(3) 0.105(6) Uani 0.50 d C -1 1 . . .
H21A H 0.1840 0.0646 0.2557 0.157 Uiso 0.50 calc C -1 1 GR . .
H21B H 0.1491 0.0763 0.4782 0.157 Uiso 0.50 calc C -1 1 GR . .
H21C H 0.1070 0.0340 0.2911 0.157 Uiso 0.50 calc C -1 1 GR . .
O4A O 0.4002(3) 0.0428(2) 0.8487(9) 0.0338(11) Uani 0.50 d A 1 1 . . .
C20 C 0.1857(9) -0.0151(6) 0.704(2) 0.087(5) Uani 0.50 d C -1 1 . . .
H20A H 0.2324 -0.0192 0.8197 0.130 Uiso 0.50 calc C -1 1 GR . .
H20B H 0.1575 -0.0501 0.6864 0.130 Uiso 0.50 calc C -1 1 GR . .
H20C H 0.1530 0.0136 0.7510 0.130 Uiso 0.50 calc C -1 1 GR . .
C12A C 0.2857(5) 0.1123(5) 0.9696(15) 0.044(2) Uani 0.50 d B 1 1 . . .
H12A H 0.3011 0.0810 1.0614 0.053 Uiso 0.50 calc B 1 1 R . .
C11A C 0.2221(6) 0.1436(5) 1.0004(17) 0.043(2) Uani 0.50 d B 1 1 . . .
H11A H 0.1962 0.1353 1.1214 0.051 Uiso 0.50 calc B 1 1 R . .
C8 C 0.2880(6) 0.1590(4) 0.6187(17) 0.032(2) Uani 0.50 d B 2 1 . U .
H8 H 0.3071 0.1603 0.4812 0.039 Uiso 0.50 calc B 2 1 R . .
C9 C 0.2221(6) 0.1878(4) 0.6355(18) 0.037(2) Uani 0.50 d B 2 1 . U .
H9 H 0.1944 0.2069 0.5082 0.045 Uiso 0.50 calc B 2 1 R . .
H3 H 0.5912(16) 0.0000 0.767(13) 0.056 Uiso 1 d . . 2 DRS T 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 O3 2.036(3) 5_657 ?
Zn1 O3 2.036(3) . ?
Zn1 O4 2.118(5) 2_657 ?
Zn1 O4 2.118(5) 6 ?
Zn1 O4 2.118(5) 5_657 ?
Zn1 O4 2.118(5) . ?
Zn1 O4A 2.103(5) 6 ?
Zn1 O4A 2.103(5) 5_657 ?
Zn1 O4A 2.103(5) 2_657 ?
Zn1 O4A 2.103(5) . ?
Zn2 Zn2 2.9034(11) 5_656 ?
Zn2 O3 1.991(2) 5_656 ?
Zn2 O3 1.991(2) . ?
Zn2 O6 1.918(2) . ?
Zn2 O6 1.918(2) 2_656 ?
O3 Zn2 1.991(2) 5_656 ?
O3 H3 0.83(2) . ?
O4 C5 1.311(7) . ?
O6 C5 1.238(4) . ?
N14 C13 1.463(6) . ?
N14 C16 1.454(5) . ?
N14 C15 1.456(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C10 1.516(5) . ?
C9A H9A 0.9500 . ?
C9A C8A 1.374(11) . ?
C9A C10 1.355(9) . ?
C11 H11 0.9500 . ?
C11 C12 1.400(14) . ?
C11 C10 1.335(11) . ?
C12 H12 0.9500 . ?
C12 C7 1.401(10) . ?
C16 C16 1.498(9) 2_556 ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C8A H8A 0.9500 . ?
C8A C7 1.366(9) . ?
C7 C5 1.483(5) . ?
C7 C12A 1.425(8) . ?
C7 C8 1.383(10) . ?
C15 C15 1.495(9) 2_556 ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C10 C11A 1.444(12) . ?
C10 C9 1.440(10) . ?
C5 O4A 1.366(6) . ?
O17 C18 1.127(9) . ?
N19 C18 1.293(9) . ?
N19 C21 1.566(17) . ?
N19 C21 1.566(17) 6 ?
N19 C20 1.438(13) 6 ?
N19 C20 1.438(13) . ?
C18 H18 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C12A H12A 0.9500 . ?
C12A C11A 1.396(12) . ?
C11A H11A 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.378(13) . ?
C9 H9 0.9500 . ?

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
O3 Zn1 O3 180.0 5_657 . ?
O3 Zn1 O4 82.40(13) 5_657 6 ?
O3 Zn1 O4 97.60(13) 5_657 5_657 ?
O3 Zn1 O4 82.40(13) . 2_657 ?
O3 Zn1 O4 97.60(13) . . ?
O3 Zn1 O4 97.60(13) . 6 ?
O3 Zn1 O4 82.40(13) . 5_657 ?
O3 Zn1 O4 82.40(13) 5_657 . ?
O3 Zn1 O4 97.60(13) 5_657 2_657 ?
O3 Zn1 O4A 86.74(16) 5_657 . ?
O3 Zn1 O4A 86.74(16) 5_657 6 ?
O3 Zn1 O4A 86.74(16) . 2_657 ?
O3 Zn1 O4A 86.74(16) . 5_657 ?
O3 Zn1 O4A 93.26(16) . 6 ?
O3 Zn1 O4A 93.26(16) . . ?
O3 Zn1 O4A 93.26(16) 5_657 5_657 ?
O3 Zn1 O4A 93.26(16) 5_657 2_657 ?
O4 Zn1 O4 180.0(3) 2_657 6 ?
O4 Zn1 O4 119.5(3) . 6 ?
O4 Zn1 O4 60.5(3) . 2_657 ?
O4 Zn1 O4 119.5(3) 2_657 5_657 ?
O4 Zn1 O4 60.5(3) 6 5_657 ?
O4 Zn1 O4 179.999(1) . 5_657 ?
O4A Zn1 O4 148.9(2) 6 2_657 ?
O4A Zn1 O4 90.1(2) 2_657 . ?
O4A Zn1 O4 148.9(2) . 5_657 ?
O4A Zn1 O4 89.9(2) 6 . ?
O4A Zn1 O4 89.9(2) 2_657 5_657 ?
O4A Zn1 O4 31.1(2) 5_657 5_657 ?
O4A Zn1 O4 148.9(2) 5_657 . ?
O4A Zn1 O4 31.1(2) 2_657 2_657 ?
O4A Zn1 O4 31.1(2) 6 6 ?
O4A Zn1 O4 90.1(2) 6 5_657 ?
O4A Zn1 O4 148.9(2) 2_657 6 ?
O4A Zn1 O4 89.9(2) 5_657 2_657 ?
O4A Zn1 O4 90.1(2) 5_657 6 ?
O4A Zn1 O4 31.1(2) . . ?
O4A Zn1 O4 90.1(2) . 2_657 ?
O4A Zn1 O4 89.9(2) . 6 ?
O4A Zn1 O4A 180.0(3) 6 2_657 ?
O4A Zn1 O4A 59.4(3) 2_657 5_657 ?
O4A Zn1 O4A 179.999(1) 5_657 . ?
O4A Zn1 O4A 120.6(3) 2_657 . ?
O4A Zn1 O4A 120.6(3) 6 5_657 ?
O4A Zn1 O4A 59.4(3) 6 . ?
O3 Zn2 Zn2 43.19(7) . 5_656 ?
O3 Zn2 Zn2 43.19(7) 5_656 5_656 ?
O3 Zn2 O3 86.38(13) 5_656 . ?
O6 Zn2 Zn2 124.27(7) 2_656 5_656 ?
O6 Zn2 Zn2 124.27(7) . 5_656 ?
O6 Zn2 O3 116.52(11) 2_656 5_656 ?
O6 Zn2 O3 116.52(11) . . ?
O6 Zn2 O3 112.00(12) . 5_656 ?
O6 Zn2 O3 112.00(12) 2_656 . ?
O6 Zn2 O6 111.46(15) 2_656 . ?
Zn1 O3 H3 99(6) . . ?
Zn2 O3 Zn1 112.01(11) 5_656 . ?
Zn2 O3 Zn1 112.01(11) . . ?
Zn2 O3 Zn2 93.62(13) 5_656 . ?
Zn2 O3 H3 120(3) 5_656 . ?
Zn2 O3 H3 120(3) . . ?
C5 O4 Zn1 131.2(4) . . ?
C5 O6 Zn2 123.8(2) . . ?
C16 N14 C13 111.4(3) . . ?
C16 N14 C15 110.5(3) . . ?
C15 N14 C13 114.6(3) . . ?
N14 C13 H13A 109.5 . . ?
N14 C13 H13B 109.5 . . ?
N14 C13 C10 110.8(3) . . ?
H13A C13 H13B 108.1 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C8A C9A H9A 118.6 . . ?
C10 C9A H9A 118.6 . . ?
C10 C9A C8A 122.7(7) . . ?
C12 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
C10 C11 C12 122.3(9) . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C7 119.4(8) . . ?
C7 C12 H12 120.3 . . ?
N14 C16 C16 110.9(3) . 2_556 ?
N14 C16 H16A 109.5 . . ?
N14 C16 H16B 109.5 . . ?
C16 C16 H16A 109.5 2_556 . ?
C16 C16 H16B 109.5 2_556 . ?
H16A C16 H16B 108.1 . . ?
C9A C8A H8A 119.7 . . ?
C7 C8A C9A 120.6(7) . . ?
C7 C8A H8A 119.7 . . ?
C12 C7 C5 122.7(5) . . ?
C12 C7 C12A 26.5(5) . . ?
C8A C7 C12 112.5(6) . . ?
C8A C7 C5 121.0(4) . . ?
C8A C7 C12A 119.8(5) . . ?
C8A C7 C8 15.6(5) . . ?
C12A C7 C5 118.9(5) . . ?
C8 C7 C12 118.4(6) . . ?
C8 C7 C5 118.7(5) . . ?
C8 C7 C12A 117.7(6) . . ?
N14 C15 C15 109.6(3) . 2_556 ?
N14 C15 H15A 109.7 . . ?
N14 C15 H15B 109.7 . . ?
C15 C15 H15A 109.7 2_556 . ?
C15 C15 H15B 109.7 2_556 . ?
H15A C15 H15B 108.2 . . ?
C9A C10 C13 119.2(5) . . ?
C9A C10 C11A 117.9(5) . . ?
C9A C10 C9 16.8(5) . . ?
C11 C10 C13 122.7(5) . . ?
C11 C10 C9A 113.7(6) . . ?
C11 C10 C11A 21.9(5) . . ?
C11 C10 C9 118.6(7) . . ?
C11A C10 C13 122.8(5) . . ?
C9 C10 C13 118.5(5) . . ?
C9 C10 C11A 115.8(6) . . ?
O4 C5 C7 117.5(4) . . ?
O4 C5 O4A 49.9(4) . . ?
O6 C5 O4 119.2(4) . . ?
O6 C5 C7 117.8(4) . . ?
O6 C5 O4A 117.4(4) . . ?
O4A C5 C7 117.6(4) . . ?
C18 N19 C21 109.4(7) . 6 ?
C18 N19 C21 109.4(7) . . ?
C18 N19 C20 128.9(9) . . ?
C18 N19 C20 128.9(9) . 6 ?
C21 N19 C21 96.9(17) 6 . ?
C20 N19 C21 91.2(10) . 6 ?
C20 N19 C21 91.2(10) 6 . ?
C20 N19 C21 113.8(8) . . ?
C20 N19 C21 113.8(8) 6 6 ?
C20 N19 C20 29.7(11) 6 . ?
O17 C18 N19 136.9(9) . . ?
O17 C18 H18 111.6 . . ?
N19 C18 H18 111.6 . . ?
N19 C21 H21A 109.5 . . ?
N19 C21 H21B 109.5 . . ?
N19 C21 H21C 109.5 . . ?
C5 O4A Zn1 128.5(4) . . ?
N19 C20 H20A 109.5 . . ?
N19 C20 H20B 109.5 . . ?
N19 C20 H20C 109.5 . . ?
C7 C12A H12A 120.7 . . ?
C11A C12A C7 118.7(8) . . ?
C11A C12A H12A 120.7 . . ?
C10 C11A H11A 120.0 . . ?
C12A C11A C10 119.9(7) . . ?
C12A C11A H11A 120.0 . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.3(8) . . ?
C9 C8 H8 119.3 . . ?
C10 C9 H9 120.4 . . ?
C8 C9 C10 119.2(8) . . ?
C8 C9 H9 120.4 . . ?

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
O3 H3 O17 0.83(2) 2.03(5) 2.781(6) 149(8) 2_656

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 O4 C5 O6 -62.5(7) . . . . ?
Zn1 O4 C5 C7 144.3(4) . . . . ?
Zn1 O4 C5 O4A 40.2(4) . . . . ?
Zn2 Zn2 O3 Zn1 -115.50(18) 5_656 . . . ?
Zn2 Zn2 O6 C5 44.4(4) 5_656 . . . ?
Zn2 O6 C5 O4 34.9(6) . . . . ?
Zn2 O6 C5 C7 -172.0(3) . . . . ?
Zn2 O6 C5 O4A -22.3(6) . . . . ?
O3 Zn1 O3 Zn2 -128.1(9) 5_657 . . . ?
O3 Zn1 O3 Zn2 128.1(10) 5_657 . . 5_656 ?
O3 Zn1 O4 C5 45.2(5) . . . . ?
O3 Zn1 O4 C5 -134.8(5) 5_657 . . . ?
O3 Zn1 O4A C5 115.7(5) 5_657 . . . ?
O3 Zn1 O4A C5 -64.3(5) . . . . ?
O3 Zn2 O3 Zn1 -115.50(18) 5_656 . . . ?
O3 Zn2 O3 Zn2 0.0 5_656 . . 5_656 ?
O3 Zn2 O6 C5 -5.4(4) . . . . ?
O3 Zn2 O6 C5 91.8(4) 5_656 . . . ?
O4 Zn1 O3 Zn2 -171.2(2) 2_657 . . 5_656 ?
O4 Zn1 O3 Zn2 -8.8(2) . . . . ?
O4 Zn1 O3 Zn2 -67.51(19) 2_657 . . . ?
O4 Zn1 O3 Zn2 171.2(2) 5_657 . . . ?
O4 Zn1 O3 Zn2 8.8(2) 6 . . 5_656 ?
O4 Zn1 O3 Zn2 -112.49(19) . . . 5_656 ?
O4 Zn1 O3 Zn2 112.49(19) 6 . . . ?
O4 Zn1 O3 Zn2 67.51(19) 5_657 . . 5_656 ?
O4 Zn1 O4 C5 -58.0(6) 6 . . . ?
O4 Zn1 O4 C5 122.0(6) 2_657 . . . ?
O4 Zn1 O4 C5 56(14) 5_657 . . . ?
O4 Zn1 O4A C5 18.0(5) 2_657 . . . ?
O4 Zn1 O4A C5 -162.0(5) 6 . . . ?
O4 Zn1 O4A C5 35.0(4) . . . . ?
O4 Zn1 O4A C5 -145.0(4) 5_657 . . . ?
O4 C5 O4A Zn1 -38.7(4) . . . . ?
O6 Zn2 O3 Zn1 -2.68(17) . . . . ?
O6 Zn2 O3 Zn1 127.31(13) 2_656 . . . ?
O6 Zn2 O3 Zn2 -117.19(11) 2_656 . . 5_656 ?
O6 Zn2 O3 Zn2 112.82(12) . . . 5_656 ?
O6 Zn2 O6 C5 -135.6(4) 2_656 . . . ?
O6 C5 O4A Zn1 67.6(7) . . . . ?
N14 C13 C10 C9A 51.8(7) . . . . ?
N14 C13 C10 C11 -153.2(6) . . . . ?
N14 C13 C10 C11A -127.0(7) . . . . ?
N14 C13 C10 C9 32.6(7) . . . . ?
C13 N14 C16 C16 -174.8(3) . . . 2_556 ?
C13 N14 C15 C15 174.0(3) . . . 2_556 ?
C13 C10 C11A C12A 178.2(9) . . . . ?
C13 C10 C9 C8 176.5(8) . . . . ?
C9A C8A C7 C12 -24.5(11) . . . . ?
C9A C8A C7 C5 177.0(7) . . . . ?
C9A C8A C7 C12A 4.0(13) . . . . ?
C9A C8A C7 C8 91(3) . . . . ?
C9A C10 C11A C12A -0.7(14) . . . . ?
C9A C10 C9 C8 79(2) . . . . ?
C11 C12 C7 C8A 26.8(11) . . . . ?
C11 C12 C7 C5 -175.1(7) . . . . ?
C11 C12 C7 C12A -85.2(16) . . . . ?
C11 C12 C7 C8 10.7(11) . . . . ?
C11 C10 C11A C12A -85.0(19) . . . . ?
C11 C10 C9 C8 2.0(13) . . . . ?
C12 C11 C10 C13 -175.3(7) . . . . ?
C12 C11 C10 C9A -19.0(11) . . . . ?
C12 C11 C10 C11A 87.3(19) . . . . ?
C12 C11 C10 C9 -1.1(12) . . . . ?
C12 C7 C5 O4 -7.2(8) . . . . ?
C12 C7 C5 O6 -160.8(6) . . . . ?
C12 C7 C5 O4A 49.6(8) . . . . ?
C12 C7 C12A C11A 74.3(17) . . . . ?
C12 C7 C8 C9 -9.9(13) . . . . ?
C16 N14 C13 C10 80.0(4) . . . . ?
C16 N14 C15 C15 -59.1(5) . . . 2_556 ?
C8A C9A C10 C13 179.0(7) . . . . ?
C8A C9A C10 C11 21.9(12) . . . . ?
C8A C9A C10 C11A -2.1(13) . . . . ?
C8A C9A C10 C9 -89(2) . . . . ?
C8A C7 C5 O4 149.0(6) . . . . ?
C8A C7 C5 O6 -4.5(8) . . . . ?
C8A C7 C5 O4A -154.2(6) . . . . ?
C8A C7 C12A C11A -6.5(14) . . . . ?
C8A C7 C8 C9 -82(2) . . . . ?
C7 C5 O4A Zn1 -142.6(4) . . . . ?
C7 C12A C11A C10 4.9(16) . . . . ?
C7 C8 C9 C10 3.6(15) . . . . ?
C15 N14 C13 C10 -153.6(4) . . . . ?
C15 N14 C16 C16 56.6(5) . . . 2_556 ?
C10 C9A C8A C7 0.4(14) . . . . ?
C10 C11 C12 C7 -5.4(13) . . . . ?
C5 C7 C12A C11A -179.7(9) . . . . ?
C5 C7 C8 C9 175.7(8) . . . . ?
C21 N19 C18 O17 52.5(10) 6 . . . ?
C21 N19 C18 O17 -52.5(10) . . . . ?
O4A Zn1 O3 Zn2 98.42(19) 5_657 . . 5_656 ?
O4A Zn1 O3 Zn2 -98.42(19) 2_657 . . . ?
O4A Zn1 O3 Zn2 157.88(19) 2_657 . . 5_656 ?
O4A Zn1 O3 Zn2 22.12(19) . . . . ?
O4A Zn1 O3 Zn2 81.58(19) 6 . . . ?
O4A Zn1 O3 Zn2 -81.58(19) . . . 5_656 ?
O4A Zn1 O3 Zn2 -22.12(19) 6 . . 5_656 ?
O4A Zn1 O3 Zn2 -157.88(19) 5_657 . . . ?
O4A Zn1 O4 C5 131.9(5) 2_657 . . . ?
O4A Zn1 O4 C5 141.6(5) 5_657 . . . ?
O4A Zn1 O4 C5 -38.4(5) . . . . ?
O4A Zn1 O4 C5 -48.1(5) 6 . . . ?
O4A Zn1 O4A C5 45(26) 5_657 . . . ?
O4A Zn1 O4A C5 23.8(4) 2_657 . . . ?
O4A Zn1 O4A C5 -156.2(4) 6 . . . ?
C20 N19 C18 O17 -160.8(8) 6 . . . ?
C20 N19 C18 O17 160.8(8) . . . . ?
C12A C7 C5 O4 -37.8(9) . . . . ?
C12A C7 C5 O6 168.6(7) . . . . ?
C12A C7 C5 O4A 19.0(9) . . . . ?
C12A C7 C8 C9 20.1(13) . . . . ?
C11A C10 C9 C8 -22.5(13) . . . . ?
C8 C7 C5 O4 166.9(6) . . . . ?
C8 C7 C5 O6 13.4(8) . . . . ?
C8 C7 C5 O4A -136.3(7) . . . . ?
C8 C7 C12A C11A -24.2(14) . . . . ?
C9 C10 C11A C12A 18.0(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT230_p-1                 
;
PROBLEM: Hirshfeld Test Diff for    O6     --  C5      ..        7.6 su    
RESPONSE: Organic backbone was disordered across two orientations. Carboxylate
oxygen atom was modelled at two ends of dynamic disorder range. Slight disorder
of solvent DMF molecule across symmetry element was not further modelled.
;
# end Validation Reply Form
