# 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 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_1
_database_code_depnum_ccdc_archive 'CCDC 1578780'
_audit_update_record             
;
2017-10-09 deposited with the CCDC.
2018-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'	C184 H176 N16 O40 Zn8, 4(C13 H14 N2), 32(H2 O)'
_chemical_formula_sum            'C236 H296 N24 O72 Zn8'
_chemical_formula_weight         5143.91

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      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_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'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   34.864(3)
_cell_length_b                   45.768(4)
_cell_length_c                   8.0403(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     12830(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4165
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      20.97

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             5392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.820
_shelx_estimated_absorpt_T_min   0.735
_shelx_estimated_absorpt_T_max   0.828
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17914
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -53
_diffrn_reflns_limit_k_max       54
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.468
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.952
_reflns_number_total             5666
_reflns_number_gt                4530
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.812
_reflns_Friedel_fraction_max     0.949
_reflns_Friedel_fraction_full    0.925

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0427P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1702 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.022(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5531
_refine_ls_number_parameters     384
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.0924
_refine_ls_wR_factor_gt          0.0864
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.002
_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 0.11054(2) 0.85383(2) 0.03898(7) 0.04239(17) Uani 1 1 d . . . . .
O1 O 0.15861(9) 0.85483(8) -0.0875(4) 0.0502(9) Uani 1 1 d . . . . .
O1W O 0.05075(18) 0.82175(16) 0.6389(10) 0.174(3) Uani 1 1 d . . . . .
H1WA H 0.0629 0.8075 0.5968 0.261 Uiso 1 1 d R U . . .
H1WB H 0.0288 0.8160 0.6710 0.261 Uiso 1 1 d R U . . .
O2 O 0.13034(9) 0.82749(8) -0.2814(5) 0.0570(10) Uani 1 1 d . . . . .
O2W O 0.26806(17) 0.98370(15) 0.3711(10) 0.158(3) Uani 1 1 d . . . . .
H2WA H 0.2801 0.9906 0.2880 0.237 Uiso 1 1 d R U . . .
H2WB H 0.2651 0.9959 0.4428 0.237 Uiso 1 1 d R U . . .
O4 O 0.29253(11) 0.88772(9) -0.1474(5) 0.0718(13) Uani 1 1 d . . . . .
O3W O 0.22034(13) 0.96806(12) 0.0934(7) 0.1085(18) Uani 1 1 d . . . . .
H3WA H 0.2092 0.9620 0.1809 0.163 Uiso 1 1 d R U . . .
H3WB H 0.2443 0.9650 0.1013 0.163 Uiso 1 1 d R U . . .
O3 O 0.32613(9) 0.87191(8) -0.3570(5) 0.0565(10) Uani 1 1 d . . . . .
O4W O 0.25270(13) 0.91104(11) 0.1197(6) 0.0976(15) Uani 1 1 d . . . . .
H4WA H 0.2657 0.9094 0.0308 0.146 Uiso 1 1 d R U . . .
H4WB H 0.2649 0.9032 0.1997 0.146 Uiso 1 1 d R U . . .
O5 O 0.22952(10) 0.81837(8) -0.7252(5) 0.0661(10) Uani 1 1 d . . . . .
N1 N 0.13051(11) 0.87608(8) 0.2441(5) 0.0437(11) Uani 1 1 d . . . . .
N2 N 0.14387(12) 1.06155(9) 0.3693(5) 0.0477(11) Uani 1 1 d . . . . .
N3 N 0.13793(14) 0.97298(15) 1.0689(8) 0.0771(16) Uani 1 1 d . . . . .
C1 C 0.16563(14) 0.88847(11) 0.2421(6) 0.0472(13) Uani 1 1 d . . . . .
H1 H 0.1809 0.8862 0.1481 0.057 Uiso 1 1 calc R U . . .
C2 C 0.17953(16) 0.90413(11) 0.3724(7) 0.0498(13) Uani 1 1 d . . . . .
H2 H 0.2039 0.9124 0.3646 0.060 Uiso 1 1 calc R U . . .
C3 C 0.15846(15) 0.90813(10) 0.5160(7) 0.0478(12) Uani 1 1 d . . . . .
C4 C 0.12294(16) 0.89473(11) 0.5186(7) 0.0545(14) Uani 1 1 d . . . . .
H4 H 0.1075 0.8964 0.6125 0.065 Uiso 1 1 calc R U . . .
C5 C 0.11034(15) 0.87926(12) 0.3860(7) 0.0532(14) Uani 1 1 d . . . . .
H5 H 0.0864 0.8703 0.3932 0.064 Uiso 1 1 calc R U . . .
C6 C 0.17318(18) 0.92693(11) 0.6561(7) 0.0619(16) Uani 1 1 d . . . . .
H6A H 0.1980 0.9196 0.6916 0.074 Uiso 1 1 calc R U . . .
H6B H 0.1557 0.9255 0.7497 0.074 Uiso 1 1 calc R U . . .
C7 C 0.17716(18) 0.95923(12) 0.6055(8) 0.0701(18) Uani 1 1 d . . . . .
H7A H 0.1856 0.9704 0.7013 0.084 Uiso 1 1 calc R U . . .
H7B H 0.1968 0.9609 0.5205 0.084 Uiso 1 1 calc R U . . .
C8 C 0.14093(16) 0.97212(13) 0.5414(10) 0.0700(17) Uani 1 1 d . . . . .
H8A H 0.1217 0.9706 0.6281 0.084 Uiso 1 1 calc R U . . .
H8B H 0.1322 0.9603 0.4486 0.084 Uiso 1 1 calc R U . . .
C9 C 0.11162(16) 1.04712(12) 0.3974(8) 0.0626(16) Uani 1 1 d . . . . .
H9 H 0.0886 1.0569 0.3792 0.075 Uiso 1 1 calc R U . . .
C10 C 0.11001(16) 1.01902(13) 0.4511(8) 0.0665(17) Uani 1 1 d . . . . .
H10 H 0.0863 1.0100 0.4656 0.080 Uiso 1 1 calc R U . . .
C11 C 0.14269(16) 1.00386(12) 0.4840(7) 0.0544(14) Uani 1 1 d . . . . .
C12 C 0.17644(18) 1.01836(14) 0.4557(10) 0.083(2) Uani 1 1 d . . . . .
H12 H 0.1997 1.0090 0.4763 0.099 Uiso 1 1 calc R U . . .
C13 C 0.17630(18) 1.04703(13) 0.3963(10) 0.083(2) Uani 1 1 d . . . . .
H13 H 0.1996 1.0562 0.3751 0.100 Uiso 1 1 calc R U . . .
C14 C 0.19462(13) 0.84341(10) -0.3261(6) 0.0362(11) Uani 1 1 d . . . . .
C15 C 0.22643(12) 0.85805(10) -0.2625(6) 0.0377(11) Uani 1 1 d . . . . .
H15 H 0.2252 0.8667 -0.1580 0.045 Uiso 1 1 calc R U . . .
C16 C 0.25984(13) 0.85981(9) -0.3545(6) 0.0374(11) Uani 1 1 d . . . . .
C17 C 0.26171(14) 0.84716(11) -0.5104(6) 0.0451(13) Uani 1 1 d . . . . .
H17 H 0.2842 0.8485 -0.5722 0.054 Uiso 1 1 calc R U . . .
C18 C 0.23016(14) 0.83254(11) -0.5751(6) 0.0452(12) Uani 1 1 d . . . . .
C19 C 0.19680(13) 0.83063(9) -0.4822(6) 0.0398(11) Uani 1 1 d . . . . .
H19 H 0.1757 0.8207 -0.5248 0.048 Uiso 1 1 calc R U . . .
C20 C 0.15822(13) 0.84147(10) -0.2264(7) 0.0418(11) Uani 1 1 d . . . . .
C21 C 0.29462(14) 0.87436(11) -0.2806(7) 0.0476(13) Uani 1 1 d . . . . .
C22 C 0.2619(2) 0.82045(17) -0.8312(8) 0.085(2) Uani 1 1 d . . . . .
H22A H 0.2852 0.8164 -0.7691 0.102 Uiso 1 1 calc R U . . .
H22B H 0.2638 0.8400 -0.8775 0.102 Uiso 1 1 calc R U . . .
C23 C 0.2572(2) 0.7990(2) -0.9641(11) 0.128(3) Uani 1 1 d . . . . .
H23A H 0.2788 0.8000 -1.0379 0.192 Uiso 1 1 calc R U . . .
H23B H 0.2555 0.7798 -0.9169 0.192 Uiso 1 1 calc R U . . .
H23C H 0.2341 0.8032 -1.0248 0.192 Uiso 1 1 calc R U . . .
C24 C 0.12874(18) 0.99998(14) 1.0235(10) 0.0746(17) Uani 1 1 d . . . . .
H24 H 0.1455 1.0150 1.0520 0.090 Uiso 1 1 calc R U . . .
C25 C 0.09635(18) 1.00713(13) 0.9380(8) 0.0654(16) Uani 1 1 d . . . . .
H25 H 0.0917 1.0265 0.9093 0.078 Uiso 1 1 calc R U . . .
C26 C 0.07038(15) 0.98573(13) 0.8936(7) 0.0550(14) Uani 1 1 d . . . . .
C27 C 0.07932(19) 0.95787(13) 0.9415(8) 0.0675(17) Uani 1 1 d . . . . .
H27 H 0.0627 0.9426 0.9168 0.081 Uiso 1 1 calc R U . . .
C28 C 0.1124(2) 0.95251(13) 1.0250(10) 0.0749(17) Uani 1 1 d . . . . .
H28 H 0.1177 0.9333 1.0540 0.090 Uiso 1 1 calc R U . . .
C29 C 0.03469(15) 0.99283(14) 0.7956(9) 0.0709(16) Uani 1 1 d . . . . .
H29A H 0.0286 0.9763 0.7250 0.085 Uiso 1 1 calc R U . . .
H29B H 0.0401 1.0093 0.7236 0.085 Uiso 1 1 calc R U . . .
C30 C 0.0000 1.0000 0.9004(11) 0.063(2) Uani 1 2 d S T P . .
H30A H 0.0059 1.0165 0.9714 0.075 Uiso 0.5 1 calc R U P . .
H30B H -0.0059 0.9835 0.9714 0.075 Uiso 0.5 1 calc R 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 1.961(3) . ?
Zn1 O3 2.013(4) 16_465 ?
Zn1 N2 2.046(4) 7_544 ?
Zn1 N1 2.060(4) . ?
Zn1 O4 2.457(4) 16_465 ?
Zn1 C21 2.568(5) 16_465 ?
O1 C20 1.274(6) . ?
O1W H1WA 0.8495 . ?
O1W H1WB 0.8502 . ?
O2 C20 1.245(6) . ?
O2W H2WA 0.8500 . ?
O2W H2WB 0.8078 . ?
O4 C21 1.235(6) . ?
O4 Zn1 2.457(4) 8_564 ?
O3W H3WA 0.8503 . ?
O3W H3WB 0.8495 . ?
O3 C21 1.264(6) . ?
O3 Zn1 2.013(4) 8_564 ?
O4W H4WA 0.8501 . ?
O4W H4WB 0.8501 . ?
O5 C18 1.370(6) . ?
O5 C22 1.419(7) . ?
N1 C5 1.348(7) . ?
N1 C1 1.349(6) . ?
N2 C9 1.323(6) . ?
N2 C13 1.329(7) . ?
N2 Zn1 2.046(4) 3 ?
N3 C24 1.328(8) . ?
N3 C28 1.340(8) . ?
C1 C2 1.358(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.381(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(7) . ?
C3 C6 1.507(8) . ?
C4 C5 1.353(8) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.540(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.486(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C11 1.525(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.358(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.360(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.370(8) . ?
C12 C13 1.396(8) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.387(7) . ?
C14 C15 1.393(6) . ?
C14 C20 1.503(7) . ?
C15 C16 1.382(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(7) . ?
C16 C21 1.506(7) . ?
C17 C18 1.389(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.385(6) . ?
C19 H19 0.9300 . ?
C21 Zn1 2.568(5) 8_564 ?
C22 C23 1.460(10) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.362(9) . ?
C24 H24 0.9300 . ?
C25 C26 1.381(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.368(8) . ?
C26 C29 1.508(8) . ?
C27 C28 1.357(9) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 C30 1.510(7) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C29 1.510(7) 2_575 ?
C30 H30A 0.9700 . ?
C30 H30B 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
O1 Zn1 O3 101.20(15) . 16_465 ?
O1 Zn1 N2 104.48(15) . 7_544 ?
O3 Zn1 N2 131.39(17) 16_465 7_544 ?
O1 Zn1 N1 96.59(15) . . ?
O3 Zn1 N1 113.31(15) 16_465 . ?
N2 Zn1 N1 103.91(16) 7_544 . ?
O1 Zn1 O4 158.33(14) . 16_465 ?
O3 Zn1 O4 57.24(13) 16_465 16_465 ?
N2 Zn1 O4 90.61(15) 7_544 16_465 ?
N1 Zn1 O4 94.68(15) . 16_465 ?
O1 Zn1 C21 130.02(17) . 16_465 ?
O3 Zn1 C21 28.92(16) 16_465 16_465 ?
N2 Zn1 C21 111.67(17) 7_544 16_465 ?
N1 Zn1 C21 106.54(16) . 16_465 ?
O4 Zn1 C21 28.35(14) 16_465 16_465 ?
C20 O1 Zn1 115.8(3) . . ?
H1WA O1W H1WB 109.5 . . ?
H2WA O2W H2WB 111.5 . . ?
C21 O4 Zn1 80.8(3) . 8_564 ?
H3WA O3W H3WB 109.5 . . ?
C21 O3 Zn1 100.7(3) . 8_564 ?
H4WA O4W H4WB 109.4 . . ?
C18 O5 C22 119.0(4) . . ?
C5 N1 C1 116.0(5) . . ?
C5 N1 Zn1 123.7(4) . . ?
C1 N1 Zn1 120.3(3) . . ?
C9 N2 C13 116.5(5) . . ?
C9 N2 Zn1 117.5(3) . 3 ?
C13 N2 Zn1 126.0(4) . 3 ?
C24 N3 C28 114.7(6) . . ?
N1 C1 C2 122.4(4) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C3 121.7(5) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C2 C3 C4 115.5(5) . . ?
C2 C3 C6 121.3(5) . . ?
C4 C3 C6 123.2(5) . . ?
C5 C4 C3 120.8(5) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
N1 C5 C4 123.6(5) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
C3 C6 C7 112.4(4) . . ?
C3 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
C3 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C6 113.3(5) . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 C11 116.7(5) . . ?
C7 C8 H8A 108.1 . . ?
C11 C8 H8A 108.1 . . ?
C7 C8 H8B 108.1 . . ?
C11 C8 H8B 108.1 . . ?
H8A C8 H8B 107.3 . . ?
N2 C9 C10 124.2(5) . . ?
N2 C9 H9 117.9 . . ?
C10 C9 H9 117.9 . . ?
C9 C10 C11 120.7(5) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C12 116.1(5) . . ?
C10 C11 C8 120.7(5) . . ?
C12 C11 C8 123.1(5) . . ?
C11 C12 C13 120.6(6) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
N2 C13 C12 121.9(6) . . ?
N2 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C19 C14 C15 119.4(4) . . ?
C19 C14 C20 120.2(4) . . ?
C15 C14 C20 120.4(4) . . ?
C16 C15 C14 120.2(5) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.0(5) . . ?
C15 C16 C21 119.6(5) . . ?
C17 C16 C21 120.3(5) . . ?
C16 C17 C18 120.3(5) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
O5 C18 C19 115.6(4) . . ?
O5 C18 C17 124.8(4) . . ?
C19 C18 C17 119.6(5) . . ?
C18 C19 C14 120.5(4) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
O2 C20 O1 124.5(5) . . ?
O2 C20 C14 120.0(5) . . ?
O1 C20 C14 115.5(4) . . ?
O4 C21 O3 121.1(5) . . ?
O4 C21 C16 120.9(5) . . ?
O3 C21 C16 118.0(5) . . ?
O4 C21 Zn1 70.8(3) . 8_564 ?
O3 C21 Zn1 50.4(2) . 8_564 ?
C16 C21 Zn1 168.2(4) . 8_564 ?
O5 C22 C23 107.7(5) . . ?
O5 C22 H22A 110.2 . . ?
C23 C22 H22A 110.2 . . ?
O5 C22 H22B 110.2 . . ?
C23 C22 H22B 110.2 . . ?
H22A C22 H22B 108.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N3 C24 C25 124.2(6) . . ?
N3 C24 H24 117.9 . . ?
C25 C24 H24 117.9 . . ?
C24 C25 C26 120.2(6) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C27 C26 C25 116.1(6) . . ?
C27 C26 C29 122.4(6) . . ?
C25 C26 C29 121.5(5) . . ?
C28 C27 C26 120.1(6) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
N3 C28 C27 124.7(6) . . ?
N3 C28 H28 117.7 . . ?
C27 C28 H28 117.7 . . ?
C26 C29 C30 114.6(6) . . ?
C26 C29 H29A 108.6 . . ?
C30 C29 H29A 108.6 . . ?
C26 C29 H29B 108.6 . . ?
C30 C29 H29B 108.6 . . ?
H29A C29 H29B 107.6 . . ?
C29 C30 C29 112.1(7) . 2_575 ?
C29 C30 H30A 109.2 . . ?
C29 C30 H30A 109.2 2_575 . ?
C29 C30 H30B 109.2 . . ?
C29 C30 H30B 109.2 2_575 . ?
H30A C30 H30B 107.9 . . ?

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.046

_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_2
_database_code_depnum_ccdc_archive 'CCDC 1578781'
_audit_update_record             
;
2017-10-09 deposited with the CCDC.
2018-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H26 N2 O6 Zn'
_chemical_formula_sum            'C24 H26 N2 O6 Zn'
_chemical_formula_weight         503.84

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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.0802(16)
_cell_length_b                   20.171(2)
_cell_length_c                   15.8618(18)
_cell_angle_alpha                90
_cell_angle_beta                 96.497(2)
_cell_angle_gamma                90
_cell_volume                     4476.1(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2726
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      23.36

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             2096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    1.141
_shelx_estimated_absorpt_T_min   0.812
_shelx_estimated_absorpt_T_max   0.830
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12555
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.093
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             3955
_reflns_number_gt                2968
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0554P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3948
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1008
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.36596(2) 0.07964(2) 0.04839(2) 0.03392(14) Uani 1 1 d . . . . .
O3 O 0.34474(16) 0.00043(10) -0.38269(13) 0.0443(5) Uani 1 1 d . . . . .
O1 O 0.38235(16) 0.06830(10) -0.07775(13) 0.0435(6) Uani 1 1 d . . . . .
O4 O 0.34088(17) 0.07718(10) -0.48414(13) 0.0482(6) Uani 1 1 d . . . . .
O1W O 0.51813(18) 0.05569(16) 0.08170(17) 0.0479(6) Uani 1 1 d . . . . .
O5 O 0.37345(17) 0.29240(10) -0.33132(13) 0.0496(6) Uani 1 1 d . . . . .
N1 N 0.37284(16) 0.14948(12) 0.14608(14) 0.0341(6) Uani 1 1 d . . . . .
C15 C 0.3685(2) 0.09568(14) -0.25503(17) 0.0321(7) Uani 1 1 d . . . . .
H15 H 0.3669 0.0514 -0.2391 0.038 Uiso 1 1 calc R U . . .
C17 C 0.3641(2) 0.17889(14) -0.36354(18) 0.0339(7) Uani 1 1 d . . . . .
H17 H 0.3604 0.1904 -0.4206 0.041 Uiso 1 1 calc R U . . .
N2 N 0.70917(17) 0.40441(12) 0.51414(15) 0.0361(6) Uani 1 1 d . . . . .
C20 C 0.3840(2) 0.12880(17) -0.09988(19) 0.0406(8) Uani 1 1 d . . . . .
O2 O 0.3874(2) 0.17460(12) -0.04799(14) 0.0659(7) Uani 1 1 d . . . . .
C14 C 0.37859(19) 0.14462(14) -0.19318(17) 0.0319(7) Uani 1 1 d . . . . .
C4 C 0.3684(2) 0.26074(15) 0.1999(2) 0.0451(8) Uani 1 1 d . . . . .
H4 H 0.3628 0.3059 0.1884 0.054 Uiso 1 1 calc R U . . .
C19 C 0.3803(2) 0.21076(15) -0.21757(18) 0.0363(7) Uani 1 1 d . . . . .
H19 H 0.3867 0.2438 -0.1764 0.044 Uiso 1 1 calc R U . . .
C3 C 0.3808(2) 0.23804(17) 0.28325(19) 0.0429(8) Uani 1 1 d . . . . .
C16 C 0.36077(19) 0.11232(14) -0.34047(17) 0.0295(6) Uani 1 1 d . . . . .
C21 C 0.3478(2) 0.06010(15) -0.40843(19) 0.0345(7) Uani 1 1 d . . . . .
C18 C 0.3728(2) 0.22787(14) -0.30228(18) 0.0351(7) Uani 1 1 d . . . . .
C1 C 0.3838(2) 0.12890(16) 0.22737(19) 0.0420(8) Uani 1 1 d . . . . .
H1 H 0.3890 0.0836 0.2379 0.050 Uiso 1 1 calc R U . . .
C22 C 0.3661(2) 0.34309(14) -0.2701(2) 0.0422(8) Uani 1 1 d . . . . .
H22A H 0.4232 0.3437 -0.2297 0.051 Uiso 1 1 calc R U . . .
H22B H 0.3115 0.3347 -0.2394 0.051 Uiso 1 1 calc R U . . .
C12 C 0.5581(2) 0.35053(17) 0.5162(2) 0.0503(9) Uani 1 1 d . . . . .
H12 H 0.5240 0.3157 0.5368 0.060 Uiso 1 1 calc R U . . .
C11 C 0.5113(2) 0.39731(17) 0.46314(19) 0.0422(8) Uani 1 1 d . . . . .
C23 C 0.3545(3) 0.40839(15) -0.3150(2) 0.0571(10) Uani 1 1 d . . . . .
H23A H 0.2960 0.4081 -0.3537 0.069 Uiso 1 1 calc R U . . .
H23B H 0.4076 0.4153 -0.3480 0.069 Uiso 1 1 calc R U . . .
C9 C 0.6632(2) 0.45011(17) 0.4646(2) 0.0493(9) Uani 1 1 d . . . . .
H9 H 0.6983 0.4856 0.4469 0.059 Uiso 1 1 calc R U . . .
C5 C 0.3645(2) 0.21476(15) 0.1334(2) 0.0411(8) Uani 1 1 d . . . . .
H5 H 0.3558 0.2304 0.0779 0.049 Uiso 1 1 calc R U . . .
C6 C 0.3880(2) 0.28296(17) 0.3620(2) 0.0529(9) Uani 1 1 d . . . . .
H6C H 0.3343 0.2734 0.3933 0.064 Uiso 1 1 calc R U . . .
H6D H 0.4459 0.2716 0.3982 0.064 Uiso 1 1 calc R U . . .
C8 C 0.4068(2) 0.39428(18) 0.4304(2) 0.0561(10) Uani 1 1 d . . . . .
H8A H 0.3823 0.4390 0.4213 0.067 Uiso 1 1 calc R U . . .
H8B H 0.3720 0.3734 0.4726 0.067 Uiso 1 1 calc R U . . .
C7 C 0.3892(2) 0.35432(17) 0.3448(2) 0.0508(9) Uani 1 1 d . . . . .
H7A H 0.3286 0.3675 0.3142 0.061 Uiso 1 1 calc R U . . .
H7B H 0.4394 0.3643 0.3097 0.061 Uiso 1 1 calc R U . . .
C10 C 0.5674(2) 0.44791(17) 0.4381(2) 0.0552(9) Uani 1 1 d . . . . .
H10 H 0.5398 0.4811 0.4028 0.066 Uiso 1 1 calc R U . . .
C13 C 0.6551(2) 0.35531(16) 0.53862(19) 0.0469(8) Uani 1 1 d . . . . .
H13 H 0.6849 0.3223 0.5730 0.056 Uiso 1 1 calc R U . . .
C2 C 0.3877(2) 0.17087(17) 0.2952(2) 0.0459(8) Uani 1 1 d . . . . .
H2 H 0.3951 0.1537 0.3500 0.055 Uiso 1 1 calc R U . . .
C24 C 0.3508(3) 0.46513(18) -0.2511(3) 0.0718(12) Uani 1 1 d . . . . .
H24A H 0.3442 0.5066 -0.2808 0.108 Uiso 1 1 calc R U . . .
H24B H 0.4088 0.4654 -0.2128 0.108 Uiso 1 1 calc R U . . .
H24C H 0.2972 0.4589 -0.2195 0.108 Uiso 1 1 calc R U . . .
H1WA H 0.565(4) 0.062(2) 0.038(3) 0.118(18) Uiso 1 1 d . . . . .
H1WB H 0.531(3) 0.0241(18) 0.091(2) 0.052(15) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O3 1.992(2) 6_556 ?
Zn1 O1 2.053(2) . ?
Zn1 N1 2.088(2) . ?
Zn1 O1W 2.202(3) . ?
Zn1 N2 2.236(2) 8_455 ?
Zn1 C20 2.591(3) . ?
O3 C21 1.273(3) . ?
O3 Zn1 1.992(2) 6 ?
O1 C20 1.271(4) . ?
O4 C21 1.243(4) . ?
O1W H1WA 1.02(6) . ?
O1W H1WB 0.67(4) . ?
O5 C18 1.381(3) . ?
O5 C22 1.422(3) . ?
N1 C5 1.335(4) . ?
N1 C1 1.347(4) . ?
C15 C14 1.388(4) . ?
C15 C16 1.388(4) . ?
C15 H15 0.9300 . ?
C17 C18 1.382(4) . ?
C17 C16 1.394(4) . ?
C17 H17 0.9300 . ?
N2 C9 1.331(4) . ?
N2 C13 1.333(4) . ?
N2 Zn1 2.236(2) 8_556 ?
C20 O2 1.235(4) . ?
C20 C14 1.507(4) . ?
C14 C19 1.390(4) . ?
C4 C3 1.392(4) . ?
C4 C5 1.401(4) . ?
C4 H4 0.9300 . ?
C19 C18 1.380(4) . ?
C19 H19 0.9300 . ?
C3 C2 1.370(4) . ?
C3 C6 1.537(4) . ?
C16 C21 1.503(4) . ?
C1 C2 1.365(4) . ?
C1 H1 0.9300 . ?
C22 C23 1.497(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C12 C13 1.375(4) . ?
C12 C11 1.381(5) . ?
C12 H12 0.9300 . ?
C11 C10 1.377(5) . ?
C11 C8 1.505(4) . ?
C23 C24 1.534(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C9 C10 1.367(5) . ?
C9 H9 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.466(4) . ?
C6 H6C 0.9700 . ?
C6 H6D 0.9700 . ?
C8 C7 1.574(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C10 H10 0.9300 . ?
C13 H13 0.9300 . ?
C2 H2 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
O3 Zn1 O1 119.02(8) 6_556 . ?
O3 Zn1 N1 97.88(9) 6_556 . ?
O1 Zn1 N1 142.89(9) . . ?
O3 Zn1 O1W 83.84(11) 6_556 . ?
O1 Zn1 O1W 89.76(9) . . ?
N1 Zn1 O1W 90.44(9) . . ?
O3 Zn1 N2 92.57(9) 6_556 8_455 ?
O1 Zn1 N2 89.77(9) . 8_455 ?
N1 Zn1 N2 92.57(9) . 8_455 ?
O1W Zn1 N2 175.60(10) . 8_455 ?
O3 Zn1 C20 147.64(10) 6_556 . ?
O1 Zn1 C20 28.90(9) . . ?
N1 Zn1 C20 114.47(10) . . ?
O1W Zn1 C20 96.25(11) . . ?
N2 Zn1 C20 85.41(9) 8_455 . ?
C21 O3 Zn1 125.31(19) . 6 ?
C20 O1 Zn1 99.79(18) . . ?
Zn1 O1W H1WA 120(3) . . ?
Zn1 O1W H1WB 119(4) . . ?
H1WA O1W H1WB 96(4) . . ?
C18 O5 C22 116.5(2) . . ?
C5 N1 C1 116.5(3) . . ?
C5 N1 Zn1 123.9(2) . . ?
C1 N1 Zn1 119.5(2) . . ?
C14 C15 C16 120.6(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C9 N2 C13 115.6(3) . . ?
C9 N2 Zn1 116.4(2) . 8_556 ?
C13 N2 Zn1 128.0(2) . 8_556 ?
O2 C20 O1 122.3(3) . . ?
O2 C20 C14 119.3(3) . . ?
O1 C20 C14 118.3(3) . . ?
O2 C20 Zn1 71.44(18) . . ?
O1 C20 Zn1 51.32(14) . . ?
C14 C20 Zn1 166.6(2) . . ?
C15 C14 C19 119.3(3) . . ?
C15 C14 C20 122.2(3) . . ?
C19 C14 C20 118.4(3) . . ?
C3 C4 C5 119.2(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C18 C19 C14 120.6(3) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
C2 C3 C4 117.1(3) . . ?
C2 C3 C6 118.3(3) . . ?
C4 C3 C6 124.6(3) . . ?
C15 C16 C17 119.2(3) . . ?
C15 C16 C21 121.3(3) . . ?
C17 C16 C21 119.4(3) . . ?
O4 C21 O3 124.8(3) . . ?
O4 C21 C16 119.2(3) . . ?
O3 C21 C16 116.0(3) . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 O5 123.9(3) . . ?
C17 C18 O5 116.3(2) . . ?
N1 C1 C2 123.6(3) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
O5 C22 C23 108.7(3) . . ?
O5 C22 H22A 110.0 . . ?
C23 C22 H22A 110.0 . . ?
O5 C22 H22B 110.0 . . ?
C23 C22 H22B 110.0 . . ?
H22A C22 H22B 108.3 . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C10 C11 C12 115.6(3) . . ?
C10 C11 C8 120.1(3) . . ?
C12 C11 C8 124.3(3) . . ?
C22 C23 C24 110.6(3) . . ?
C22 C23 H23A 109.5 . . ?
C24 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 108.1 . . ?
N2 C9 C10 123.7(3) . . ?
N2 C9 H9 118.1 . . ?
C10 C9 H9 118.1 . . ?
N1 C5 C4 123.0(3) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
C7 C6 C3 115.4(3) . . ?
C7 C6 H6C 108.4 . . ?
C3 C6 H6C 108.4 . . ?
C7 C6 H6D 108.4 . . ?
C3 C6 H6D 108.4 . . ?
H6C C6 H6D 107.5 . . ?
C11 C8 C7 111.8(3) . . ?
C11 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C11 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C6 C7 C8 110.3(3) . . ?
C6 C7 H7A 109.6 . . ?
C8 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C9 C10 C11 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
N2 C13 C12 124.0(3) . . ?
N2 C13 H13 118.0 . . ?
C12 C13 H13 118.0 . . ?
C1 C2 C3 120.6(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         0.555
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.064

_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_3
_database_code_depnum_ccdc_archive 'CCDC 1578782'
_audit_update_record             
;
2017-10-09 deposited with the CCDC.
2018-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '	C25 H26 N2 O5 Zn, 2(H2 O)	'
_chemical_formula_sum            'C25 H30 N2 O7 Zn'
_chemical_formula_weight         535.88

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      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                   7.5609(8)
_cell_length_b                   19.205(2)
_cell_length_c                   17.8092(19)
_cell_angle_alpha                90
_cell_angle_beta                 98.4260(10)
_cell_angle_gamma                90
_cell_volume                     2558.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2993
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      21.88

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    1.006
_shelx_estimated_absorpt_T_min   0.766
_shelx_estimated_absorpt_T_max   0.817
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14242
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.121
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             4494
_reflns_number_gt                3114
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1176P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4484
_refine_ls_number_parameters     365
_refine_ls_number_restraints     654
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1782
_refine_ls_wR_factor_gt          0.1610
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.061
_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 0.22560(6) 0.21188(2) 0.83953(3) 0.0450(2) Uani 1 1 d . . . . .
O3 O 0.5494(4) 0.29228(14) 1.24737(17) 0.0510(8) Uani 1 1 d . . . . .
N1 N 0.3193(4) 0.11269(17) 0.86319(19) 0.0447(8) Uani 1 1 d . . . . .
N2 N 1.0774(5) -0.23463(18) 0.7056(2) 0.0464(8) Uani 1 1 d . . . . .
C9 C 1.1065(6) -0.2150(2) 0.7789(3) 0.0559(11) Uani 1 1 d . U . . .
H9 H 1.2153 -0.2263 0.8079 0.067 Uiso 1 1 calc R U . . .
C21 C 0.4104(5) 0.3295(2) 1.2491(2) 0.0460(9) Uani 1 1 d . U . . .
O4 O 0.3732(4) 0.35847(17) 1.30660(17) 0.0580(8) Uani 1 1 d . . . . .
C20 C 0.2474(7) 0.2707(3) 0.9731(3) 0.0593(11) Uani 1 1 d . U . . .
C15 C 0.3256(6) 0.3040(2) 1.1098(3) 0.0488(10) Uani 1 1 d . U . . .
H15 H 0.4298 0.2780 1.1111 0.059 Uiso 1 1 calc R U . . .
C3 C 0.4612(6) -0.0200(2) 0.8983(3) 0.0509(10) Uani 1 1 d . U . . .
C7 C 0.7039(6) -0.1137(2) 0.8896(3) 0.0572(11) Uani 1 1 d . U . . .
H7A H 0.7934 -0.0775 0.9003 0.069 Uiso 1 1 calc R U . . .
H7B H 0.7507 -0.1557 0.9157 0.069 Uiso 1 1 calc R U . . .
C13 C 0.9169(6) -0.2189(2) 0.6670(3) 0.0527(10) Uani 1 1 d . U . . .
H13 H 0.8924 -0.2323 0.6164 0.063 Uiso 1 1 calc R U . . .
C11 C 0.8157(6) -0.1632(2) 0.7717(3) 0.0497(10) Uani 1 1 d . U . . .
C10 C 0.9821(6) -0.1789(2) 0.8129(3) 0.0544(10) Uani 1 1 d . U . . .
H10 H 1.0092 -0.1651 0.8634 0.065 Uiso 1 1 calc R U . . .
C12 C 0.7884(6) -0.1847(2) 0.6975(3) 0.0539(10) Uani 1 1 d . U . . .
H12 H 0.6794 -0.1755 0.6676 0.065 Uiso 1 1 calc R U . . .
C16 C 0.2894(5) 0.3364(2) 1.1753(2) 0.0480(10) Uani 1 1 d . U . . .
C1 C 0.4921(6) 0.0990(2) 0.8656(3) 0.0523(10) Uani 1 1 d . U . . .
H1 H 0.5675 0.1350 0.8555 0.063 Uiso 1 1 calc R U . . .
C6 C 0.5326(7) -0.0914(2) 0.9203(3) 0.0584(11) Uani 1 1 d . U . . .
H6A H 0.4398 -0.1251 0.9033 0.070 Uiso 1 1 calc R U . . .
H6B H 0.5554 -0.0938 0.9753 0.070 Uiso 1 1 calc R U . . .
C14 C 0.2101(6) 0.3095(3) 1.0425(3) 0.0550(10) Uani 1 1 d . U . . .
C8 C 0.6709(6) -0.1272(3) 0.8056(3) 0.0598(11) Uani 1 1 d . U . . .
H8A H 0.5629 -0.1549 0.7946 0.072 Uiso 1 1 calc R U . . .
H8B H 0.6477 -0.0829 0.7800 0.072 Uiso 1 1 calc R U . . .
C2 C 0.5653(6) 0.0343(2) 0.8822(3) 0.0548(10) Uani 1 1 d . U . . .
H2 H 0.6871 0.0275 0.8824 0.066 Uiso 1 1 calc R U . . .
O2 O 0.3931(5) 0.24179(18) 0.97385(18) 0.0677(9) Uani 1 1 d . U . . .
C5 C 0.2169(6) 0.0602(2) 0.8787(3) 0.0650(12) Uani 1 1 d . U . . .
H5 H 0.0954 0.0683 0.8782 0.078 Uiso 1 1 calc R U . . .
C4 C 0.2811(6) -0.0055(2) 0.8954(3) 0.0649(12) Uani 1 1 d . U . . .
H4 H 0.2029 -0.0407 0.9049 0.078 Uiso 1 1 calc R U . . .
O1 O 0.1264(5) 0.26829(19) 0.91646(18) 0.0734(10) Uani 1 1 d . . . . .
C17 C 0.1356(7) 0.3765(3) 1.1721(3) 0.0694(12) Uani 1 1 d . U . . .
H17 H 0.1082 0.3983 1.2156 0.083 Uiso 1 1 calc R U . . .
C19 C 0.0596(7) 0.3491(3) 1.0395(3) 0.0710(12) Uani 1 1 d . U . . .
H19 H -0.0188 0.3527 0.9943 0.085 Uiso 1 1 calc R U . . .
C18 C 0.0232(7) 0.3840(3) 1.1040(3) 0.0806(13) Uani 1 1 d . U . . .
O5 O -0.1117(17) 0.4393(6) 1.0947(7) 0.099(4) Uani 0.538(7) 1 d D U P A 1
C22 C -0.1363(18) 0.4877(8) 1.1550(8) 0.112(2) Uani 0.538(7) 1 d D U P A 1
H22A H -0.0340 0.5186 1.1644 0.134 Uiso 0.538(7) 1 calc R U P A 1
H22B H -0.1439 0.4620 1.2014 0.134 Uiso 0.538(7) 1 calc R U P A 1
C23 C -0.3007(18) 0.5291(8) 1.1343(11) 0.126(3) Uani 0.538(7) 1 d D U P A 1
H23A H -0.3031 0.5645 1.1730 0.152 Uiso 0.538(7) 1 calc R U P A 1
H23B H -0.2905 0.5531 1.0872 0.152 Uiso 0.538(7) 1 calc R U P A 1
C24 C -0.4697(19) 0.4944(9) 1.1247(11) 0.130(3) Uani 0.538(7) 1 d D U P A 1
H24A H -0.4828 0.4734 1.1731 0.156 Uiso 0.538(7) 1 calc R U P A 1
H24B H -0.4627 0.4565 1.0893 0.156 Uiso 0.538(7) 1 calc R U P A 1
C25 C -0.631(2) 0.5315(9) 1.0993(11) 0.147(4) Uani 0.538(7) 1 d D U P A 1
H25A H -0.7310 0.5001 1.0963 0.220 Uiso 0.538(7) 1 calc R U P A 1
H25B H -0.6460 0.5681 1.1346 0.220 Uiso 0.538(7) 1 calc R U P A 1
H25C H -0.6258 0.5511 1.0502 0.220 Uiso 0.538(7) 1 calc R U P A 1
C22' C -0.2206(18) 0.4302(10) 1.1595(8) 0.105(2) Uani 0.462(7) 1 d D U P A 2
H22C H -0.1323 0.4628 1.1839 0.126 Uiso 0.462(7) 1 calc R U P A 2
H22D H -0.2360 0.3938 1.1958 0.126 Uiso 0.462(7) 1 calc R U P A 2
C23' C -0.3913(19) 0.4667(8) 1.1381(11) 0.117(3) Uani 0.462(7) 1 d D U P A 2
H23C H -0.4413 0.4781 1.1837 0.141 Uiso 0.462(7) 1 calc R U P A 2
H23D H -0.4744 0.4357 1.1077 0.141 Uiso 0.462(7) 1 calc R U P A 2
C24' C -0.372(2) 0.5327(9) 1.0938(11) 0.123(3) Uani 0.462(7) 1 d D U P A 2
H24C H -0.3891 0.5214 1.0401 0.148 Uiso 0.462(7) 1 calc R U P A 2
H24D H -0.4670 0.5645 1.1023 0.148 Uiso 0.462(7) 1 calc R U P A 2
C25' C -0.203(2) 0.5681(10) 1.1126(13) 0.152(4) Uani 0.462(7) 1 d D U P A 2
H25D H -0.2025 0.6092 1.0820 0.228 Uiso 0.462(7) 1 calc R U P A 2
H25E H -0.1862 0.5809 1.1652 0.228 Uiso 0.462(7) 1 calc R U P A 2
H25F H -0.1081 0.5377 1.1030 0.228 Uiso 0.462(7) 1 calc R U P A 2
O5' O -0.1578(19) 0.4004(7) 1.0960(9) 0.096(4) Uani 0.462(7) 1 d D U P A 2
O1W O 0.7258(10) 0.2469(6) 1.0450(5) 0.246(5) Uani 1 1 d G . . . .
H1WA H 0.7715 0.2874 1.0477 0.369 Uiso 1 1 d DG U . . .
H1WB H 0.6141 0.2539 1.0423 0.369 Uiso 1 1 d DG U . . .
O2W O 0.8800(9) 0.1509(4) 0.9810(3) 0.183(3) Uani 1 1 d . . . . .
H2WA H 0.8709 0.1579 0.9334 0.274 Uiso 1 1 d R U . . .
H2WB H 0.8109 0.1787 0.9999 0.274 Uiso 1 1 d DR 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 O3 1.958(3) 4_565 ?
Zn1 O1 1.978(4) . ?
Zn1 N1 2.054(3) . ?
Zn1 N2 2.066(4) 2_656 ?
O3 C21 1.275(5) . ?
O3 Zn1 1.958(3) 4_666 ?
N1 C5 1.325(6) . ?
N1 C1 1.328(5) . ?
N2 C13 1.339(5) . ?
N2 C9 1.346(6) . ?
N2 Zn1 2.066(4) 2_646 ?
C9 C10 1.378(6) . ?
C9 H9 0.9300 . ?
C21 O4 1.233(5) . ?
C21 C16 1.493(6) . ?
C20 O2 1.232(6) . ?
C20 O1 1.260(6) . ?
C20 C14 1.504(7) . ?
C15 C14 1.379(6) . ?
C15 C16 1.386(6) . ?
C15 H15 0.9300 . ?
C3 C2 1.362(6) . ?
C3 C4 1.383(6) . ?
C3 C6 1.504(6) . ?
C7 C8 1.502(6) . ?
C7 C6 1.539(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C13 C12 1.351(6) . ?
C13 H13 0.9300 . ?
C11 C12 1.370(6) . ?
C11 C10 1.394(6) . ?
C11 C8 1.495(6) . ?
C10 H10 0.9300 . ?
C12 H12 0.9300 . ?
C16 C17 1.390(6) . ?
C1 C2 1.375(6) . ?
C1 H1 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C14 C19 1.363(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C2 H2 0.9300 . ?
C5 C4 1.368(6) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C17 C18 1.383(7) . ?
C17 H17 0.9300 . ?
C19 C18 1.392(7) . ?
C19 H19 0.9300 . ?
C18 O5' 1.391(15) . ?
C18 O5 1.464(12) . ?
O5 C22 1.454(13) . ?
C22 C23 1.476(14) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.429(15) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.429(15) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C22' O5' 1.410(15) . ?
C22' C23' 1.468(14) . ?
C22' H22C 0.9700 . ?
C22' H22D 0.9700 . ?
C23' C24' 1.512(16) . ?
C23' H23C 0.9700 . ?
C23' H23D 0.9700 . ?
C24' C25' 1.443(16) . ?
C24' H24C 0.9700 . ?
C24' H24D 0.9700 . ?
C25' H25D 0.9600 . ?
C25' H25E 0.9600 . ?
C25' H25F 0.9600 . ?
O1W H1WA 0.8502 . ?
O1W H1WB 0.8501 . ?
O2W H2WA 0.8499 . ?
O2W H2WB 0.8500 . ?

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 O1 108.82(14) 4_565 . ?
O3 Zn1 N1 107.81(13) 4_565 . ?
O1 Zn1 N1 121.32(15) . . ?
O3 Zn1 N2 97.74(13) 4_565 2_656 ?
O1 Zn1 N2 111.41(15) . 2_656 ?
N1 Zn1 N2 107.12(13) . 2_656 ?
C21 O3 Zn1 117.7(3) . 4_666 ?
C5 N1 C1 116.4(4) . . ?
C5 N1 Zn1 123.6(3) . . ?
C1 N1 Zn1 119.9(3) . . ?
C13 N2 C9 116.2(4) . . ?
C13 N2 Zn1 124.3(3) . 2_646 ?
C9 N2 Zn1 119.5(3) . 2_646 ?
N2 C9 C10 122.9(4) . . ?
N2 C9 H9 118.6 . . ?
C10 C9 H9 118.6 . . ?
O4 C21 O3 124.3(4) . . ?
O4 C21 C16 120.3(4) . . ?
O3 C21 C16 115.4(4) . . ?
O2 C20 O1 122.3(5) . . ?
O2 C20 C14 119.3(4) . . ?
O1 C20 C14 118.4(5) . . ?
C14 C15 C16 121.3(4) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C2 C3 C4 115.7(4) . . ?
C2 C3 C6 123.8(4) . . ?
C4 C3 C6 120.5(4) . . ?
C8 C7 C6 112.1(4) . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
N2 C13 C12 123.7(4) . . ?
N2 C13 H13 118.2 . . ?
C12 C13 H13 118.2 . . ?
C12 C11 C10 116.1(4) . . ?
C12 C11 C8 120.9(4) . . ?
C10 C11 C8 123.0(4) . . ?
C9 C10 C11 119.9(4) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C13 C12 C11 121.2(4) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C15 C16 C17 118.8(4) . . ?
C15 C16 C21 122.0(4) . . ?
C17 C16 C21 119.2(4) . . ?
N1 C1 C2 123.3(4) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C3 C6 C7 116.8(4) . . ?
C3 C6 H6A 108.1 . . ?
C7 C6 H6A 108.1 . . ?
C3 C6 H6B 108.1 . . ?
C7 C6 H6B 108.1 . . ?
H6A C6 H6B 107.3 . . ?
C19 C14 C15 119.7(4) . . ?
C19 C14 C20 120.0(4) . . ?
C15 C14 C20 120.3(4) . . ?
C11 C8 C7 117.2(4) . . ?
C11 C8 H8A 108.0 . . ?
C7 C8 H8A 108.0 . . ?
C11 C8 H8B 108.0 . . ?
C7 C8 H8B 108.0 . . ?
H8A C8 H8B 107.2 . . ?
C3 C2 C1 120.7(4) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
N1 C5 C4 123.2(4) . . ?
N1 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
C5 C4 C3 120.7(4) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C20 O1 Zn1 105.7(3) . . ?
C18 C17 C16 119.8(5) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C14 C19 C18 120.1(5) . . ?
C14 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C17 C18 O5' 125.6(8) . . ?
C17 C18 C19 120.2(5) . . ?
O5' C18 C19 109.6(7) . . ?
C17 C18 O5 120.2(7) . . ?
C19 C18 O5 118.3(6) . . ?
C22 O5 C18 122.8(10) . . ?
O5 C22 C23 110.7(12) . . ?
O5 C22 H22A 109.5 . . ?
C23 C22 H22A 109.5 . . ?
O5 C22 H22B 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
C24 C23 C22 119.0(15) . . ?
C24 C23 H23A 107.6 . . ?
C22 C23 H23A 107.6 . . ?
C24 C23 H23B 107.6 . . ?
C22 C23 H23B 107.6 . . ?
H23A C23 H23B 107.0 . . ?
C23 C24 C25 121.0(15) . . ?
C23 C24 H24A 107.1 . . ?
C25 C24 H24A 107.1 . . ?
C23 C24 H24B 107.1 . . ?
C25 C24 H24B 107.1 . . ?
H24A C24 H24B 106.8 . . ?
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 . . ?
O5' C22' C23' 111.8(13) . . ?
O5' C22' H22C 109.2 . . ?
C23' C22' H22C 109.2 . . ?
O5' C22' H22D 109.2 . . ?
C23' C22' H22D 109.2 . . ?
H22C C22' H22D 107.9 . . ?
C22' C23' C24' 112.8(15) . . ?
C22' C23' H23C 109.0 . . ?
C24' C23' H23C 109.0 . . ?
C22' C23' H23D 109.0 . . ?
C24' C23' H23D 109.0 . . ?
H23C C23' H23D 107.8 . . ?
C25' C24' C23' 115.0(14) . . ?
C25' C24' H24C 108.5 . . ?
C23' C24' H24C 108.5 . . ?
C25' C24' H24D 108.5 . . ?
C23' C24' H24D 108.5 . . ?
H24C C24' H24D 107.5 . . ?
C24' C25' H25D 109.5 . . ?
C24' C25' H25E 109.5 . . ?
H25D C25' H25E 109.5 . . ?
C24' C25' H25F 109.5 . . ?
H25D C25' H25F 109.5 . . ?
H25E C25' H25F 109.5 . . ?
C18 O5' C22' 116.9(12) . . ?
H1WA O1W H1WB 104.5 . . ?
H2WA O2W H2WB 109.5 . . ?

_refine_diff_density_max         0.487
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.081

_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_4
_database_code_depnum_ccdc_archive 'CCDC 1578783'
_audit_update_record             
;
2017-10-09 deposited with the CCDC.
2018-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H26 N2 O5 Zn'
_chemical_formula_sum            'C25 H26 N2 O5 Zn'
_chemical_formula_weight         499.85

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      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                   7.3754(8)
_cell_length_b                   19.291(2)
_cell_length_c                   18.0017(19)
_cell_angle_alpha                90
_cell_angle_beta                 98.6690(10)
_cell_angle_gamma                90
_cell_volume                     2531.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3201
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      22.97

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.006
_shelx_estimated_absorpt_T_min   0.824
_shelx_estimated_absorpt_T_max   0.856
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13994
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.402
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             4461
_reflns_number_gt                3274
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0424P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4424
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0883
_refine_ls_wR_factor_gt          0.0811
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.72459(4) 0.21234(2) 0.84210(2) 0.03613(12) Uani 1 1 d . . . . .
O3 O 1.0494(2) 0.29299(9) 1.24940(10) 0.0423(4) Uani 1 1 d . . . . .
O4 O 0.8652(2) 0.35874(10) 1.30631(9) 0.0470(5) Uani 1 1 d . . . . .
N1 N 0.9257(3) 0.26549(10) 0.79725(12) 0.0374(5) Uani 1 1 d . . . . .
O2 O 0.9032(3) 0.24333(11) 0.97694(10) 0.0587(6) Uani 1 1 d . . . . .
O1 O 0.6248(3) 0.26613(10) 0.91900(11) 0.0583(6) Uani 1 1 d . . . . .
C5 C 1.0891(4) 0.28424(13) 0.83668(15) 0.0404(6) Uani 1 1 d . . . . .
H5 H 1.1126 0.2735 0.8876 0.049 Uiso 1 1 calc R U . . .
N2 N 1.6832(3) 0.61392(10) 0.63232(11) 0.0366(5) Uani 1 1 d . . . . .
C15 C 0.8267(4) 0.30451(12) 1.11120(14) 0.0388(6) Uani 1 1 d . . . . .
H15 H 0.9361 0.2800 1.1135 0.047 Uiso 1 1 calc R U . . .
C1 C 0.8975(4) 0.28300(13) 0.72385(16) 0.0426(7) Uani 1 1 d . . . . .
H1 H 0.7865 0.2709 0.6951 0.051 Uiso 1 1 calc R U . . .
C11 C 1.5474(4) 0.47933(13) 0.60017(14) 0.0376(6) Uani 1 1 d . . . . .
C21 C 0.9051(4) 0.32987(13) 1.24958(14) 0.0356(6) Uani 1 1 d . . . . .
C7 C 1.3060(4) 0.38386(13) 0.61179(15) 0.0461(7) Uani 1 1 d . . . . .
H7A H 1.2104 0.4183 0.5998 0.055 Uiso 1 1 calc R U . . .
H7B H 1.2622 0.3408 0.5877 0.055 Uiso 1 1 calc R U . . .
C16 C 0.7826(4) 0.33708(13) 1.17553(13) 0.0357(6) Uani 1 1 d . . . . .
C20 C 0.7520(5) 0.27013(14) 0.97561(16) 0.0470(8) Uani 1 1 d . . . . .
C13 C 1.5099(4) 0.59797(13) 0.63530(14) 0.0404(6) Uani 1 1 d . . . . .
H13 H 1.4325 0.6326 0.6482 0.049 Uiso 1 1 calc R U . . .
C4 C 1.2211(4) 0.31819(14) 0.80517(14) 0.0414(6) Uani 1 1 d . . . . .
H4 H 1.3320 0.3292 0.8347 0.050 Uiso 1 1 calc R U . . .
C3 C 1.1926(3) 0.33640(12) 0.73046(14) 0.0359(6) Uani 1 1 d . . . . .
C2 C 1.0248(4) 0.31774(14) 0.68958(15) 0.0427(7) Uani 1 1 d . . . . .
H2 H 0.9985 0.3288 0.6388 0.051 Uiso 1 1 calc R U . . .
C8 C 1.4759(4) 0.40727(13) 0.58021(15) 0.0471(7) Uani 1 1 d . . . . .
H8A H 1.5737 0.3746 0.5968 0.057 Uiso 1 1 calc R U . . .
H8B H 1.4497 0.4041 0.5259 0.057 Uiso 1 1 calc R U . . .
C12 C 1.4386(4) 0.53266(13) 0.62027(15) 0.0446(7) Uani 1 1 d . . . . .
H12 H 1.3159 0.5242 0.6236 0.054 Uiso 1 1 calc R U . . .
C19 C 0.5492(4) 0.34671(15) 1.03988(15) 0.0530(8) Uani 1 1 d . . . . .
H19 H 0.4706 0.3501 0.9945 0.064 Uiso 1 1 calc R U . . .
O5 O 0.3439(3) 0.41711(12) 1.09255(11) 0.0748(7) Uani 1 1 d . . . . .
C17 C 0.6218(4) 0.37555(13) 1.17097(15) 0.0435(7) Uani 1 1 d . . . . .
H17 H 0.5928 0.3980 1.2134 0.052 Uiso 1 1 calc R U . . .
C14 C 0.7069(4) 0.30874(13) 1.04381(14) 0.0415(7) Uani 1 1 d . . . . .
C18 C 0.5051(4) 0.38051(15) 1.10341(16) 0.0514(8) Uani 1 1 d . . . . .
C6 C 1.3409(4) 0.37308(15) 0.69634(15) 0.0493(7) Uani 1 1 d . . . . .
H6A H 1.4537 0.3469 0.7087 0.059 Uiso 1 1 calc R U . . .
H6B H 1.3609 0.4181 0.7201 0.059 Uiso 1 1 calc R U . . .
C10 C 1.7256(4) 0.49663(13) 0.59590(17) 0.0498(7) Uani 1 1 d . . . . .
H10 H 1.8046 0.4632 0.5818 0.060 Uiso 1 1 calc R U . . .
C9 C 1.7897(4) 0.56276(14) 0.61210(17) 0.0506(8) Uani 1 1 d . . . . .
H9 H 1.9118 0.5725 0.6089 0.061 Uiso 1 1 calc R U . . .
C22 C 0.2839(5) 0.44875(19) 1.15576(18) 0.0685(10) Uani 1 1 d . . . . .
H22A H 0.3789 0.4790 1.1809 0.082 Uiso 1 1 calc R U . . .
H22B H 0.2579 0.4136 1.1912 0.082 Uiso 1 1 calc R U . . .
C23 C 0.1128(5) 0.49008(17) 1.12876(19) 0.0700(10) Uani 1 1 d . . . . .
H23 H 0.0251 0.4594 1.0985 0.084 Uiso 1 1 calc R U . . .
C25 C 0.0266(6) 0.51466(19) 1.1958(2) 0.0973(14) Uani 1 1 d . . . . .
H25A H 0.0103 0.4758 1.2276 0.146 Uiso 1 1 calc R U . . .
H25B H -0.0904 0.5354 1.1784 0.146 Uiso 1 1 calc R U . . .
H25C H 0.1054 0.5482 1.2238 0.146 Uiso 1 1 calc R U . . .
C24 C 0.1556(7) 0.5493(2) 1.0795(3) 0.1201(17) Uani 1 1 d . . . . .
H24A H 0.2344 0.5819 1.1090 0.180 Uiso 1 1 calc R U . . .
H24B H 0.0437 0.5719 1.0584 0.180 Uiso 1 1 calc R U . . .
H24C H 0.2161 0.5318 1.0397 0.180 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 O3 1.9531(19) 4_565 ?
Zn1 O1 1.9602(18) . ?
Zn1 N2 2.045(2) 2_746 ?
Zn1 N1 2.065(2) . ?
O3 C21 1.281(3) . ?
O3 Zn1 1.9531(18) 4_666 ?
O4 C21 1.237(3) . ?
N1 C1 1.349(3) . ?
N1 C5 1.352(3) . ?
O2 C20 1.226(3) . ?
O1 C20 1.279(4) . ?
C5 C4 1.366(4) . ?
C5 H5 0.9300 . ?
N2 C13 1.324(3) . ?
N2 C9 1.345(3) . ?
N2 Zn1 2.046(2) 2_756 ?
C15 C14 1.392(4) . ?
C15 C16 1.398(3) . ?
C15 H15 0.9300 . ?
C1 C2 1.373(4) . ?
C1 H1 0.9300 . ?
C11 C10 1.370(4) . ?
C11 C12 1.386(3) . ?
C11 C8 1.511(3) . ?
C21 C16 1.500(3) . ?
C7 C6 1.519(4) . ?
C7 C8 1.521(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C16 C17 1.391(3) . ?
C20 C14 1.515(4) . ?
C13 C12 1.376(3) . ?
C13 H13 0.9300 . ?
C4 C3 1.375(3) . ?
C4 H4 0.9300 . ?
C3 C2 1.388(4) . ?
C3 C6 1.509(3) . ?
C2 H2 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C12 H12 0.9300 . ?
C19 C14 1.367(4) . ?
C19 C18 1.397(4) . ?
C19 H19 0.9300 . ?
O5 C18 1.371(3) . ?
O5 C22 1.419(4) . ?
C17 C18 1.384(4) . ?
C17 H17 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C10 C9 1.376(3) . ?
C10 H10 0.9300 . ?
C9 H9 0.9300 . ?
C22 C23 1.510(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.509(5) . ?
C23 C25 1.523(5) . ?
C23 H23 0.9800 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
O3 Zn1 O1 111.15(8) 4_565 . ?
O3 Zn1 N2 107.34(8) 4_565 2_746 ?
O1 Zn1 N2 118.68(8) . 2_746 ?
O3 Zn1 N1 96.53(8) 4_565 . ?
O1 Zn1 N1 112.43(9) . . ?
N2 Zn1 N1 108.35(8) 2_746 . ?
C21 O3 Zn1 118.03(15) . 4_666 ?
C1 N1 C5 116.2(2) . . ?
C1 N1 Zn1 119.56(18) . . ?
C5 N1 Zn1 124.28(17) . . ?
C20 O1 Zn1 106.62(19) . . ?
N1 C5 C4 123.0(2) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
C13 N2 C9 116.6(2) . . ?
C13 N2 Zn1 119.79(17) . 2_756 ?
C9 N2 Zn1 123.64(18) . 2_756 ?
C14 C15 C16 119.9(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
N1 C1 C2 123.2(3) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C10 C11 C12 115.6(2) . . ?
C10 C11 C8 121.0(2) . . ?
C12 C11 C8 123.4(2) . . ?
O4 C21 O3 123.6(2) . . ?
O4 C21 C16 120.4(2) . . ?
O3 C21 C16 116.0(2) . . ?
C6 C7 C8 113.0(2) . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C17 C16 C15 119.6(2) . . ?
C17 C16 C21 119.7(2) . . ?
C15 C16 C21 120.7(2) . . ?
O2 C20 O1 123.1(3) . . ?
O2 C20 C14 120.1(3) . . ?
O1 C20 C14 116.8(3) . . ?
N2 C13 C12 123.2(2) . . ?
N2 C13 H13 118.4 . . ?
C12 C13 H13 118.4 . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C3 C2 116.4(2) . . ?
C4 C3 C6 120.3(2) . . ?
C2 C3 C6 123.3(2) . . ?
C1 C2 C3 120.2(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C11 C8 C7 117.5(2) . . ?
C11 C8 H8A 107.9 . . ?
C7 C8 H8A 107.9 . . ?
C11 C8 H8B 107.9 . . ?
C7 C8 H8B 107.9 . . ?
H8A C8 H8B 107.2 . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C19 C18 120.6(3) . . ?
C14 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C18 O5 C22 118.4(2) . . ?
C18 C17 C16 120.1(2) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C14 C15 120.0(2) . . ?
C19 C14 C20 120.7(3) . . ?
C15 C14 C20 119.3(3) . . ?
O5 C18 C17 124.9(2) . . ?
O5 C18 C19 115.3(3) . . ?
C17 C18 C19 119.8(3) . . ?
C3 C6 C7 116.6(2) . . ?
C3 C6 H6A 108.1 . . ?
C7 C6 H6A 108.1 . . ?
C3 C6 H6B 108.1 . . ?
C7 C6 H6B 108.1 . . ?
H6A C6 H6B 107.3 . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
N2 C9 C10 122.8(3) . . ?
N2 C9 H9 118.6 . . ?
C10 C9 H9 118.6 . . ?
O5 C22 C23 108.4(3) . . ?
O5 C22 H22A 110.0 . . ?
C23 C22 H22A 110.0 . . ?
O5 C22 H22B 110.0 . . ?
C23 C22 H22B 110.0 . . ?
H22A C22 H22B 108.4 . . ?
C24 C23 C22 110.5(3) . . ?
C24 C23 C25 112.3(3) . . ?
C22 C23 C25 109.7(3) . . ?
C24 C23 H23 108.0 . . ?
C22 C23 H23 108.0 . . ?
C25 C23 H23 108.0 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         0.281
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.051

_shelxl_version_number           2014-3

