# 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_cd10710_001_sq
_database_code_depnum_ccdc_archive 'CCDC 1004887'

_audit_update_record             
;
2014-05-22 deposited with the CCDC.
2015-06-22 downloaded from the CCDC.
;
_publcif_datablock.id            {87d4c8fb-1498-4e36-9dea-98e36e82bde7}

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N2 O11 Zn2'
_chemical_formula_sum            'C20 H22 N2 O11 Zn2'
_chemical_formula_weight         597.13



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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   15.023(2)
_cell_length_b                   10.1643(13)
_cell_length_c                   18.196(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.233(2)
_cell_angle_gamma                90
_cell_volume                     2533.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    14247
_cell_measurement_theta_min      1.4893
_cell_measurement_theta_max      27.7415

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    1.951
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.704
_exptl_absorpt_correction_T_max  0.813
_exptl_absorpt_process_details   'Jacobson, R. (1998), Private communication'

_exptl_special_details           ?

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Rigaku, AFC-7'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       
;
Mercury (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 14.6306
_diffrn_measurement_method       dtprofit.ref

_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_measurement_details      
;
scan:
	Number of images: 180
	           Slice: 0.0000 - 360.0000
	     Image width: 2.0000
	        Exp time: 60.0000
	   Rotation axis: Phi
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 0.0000
	             XTD: 42.3300
	          2theta: -10.0889
scan:
	Number of images: 17
	           Slice: -24.0000 - 10.0000
	     Image width: 2.0000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 0.0000
	             XTD: 42.3300
	          2theta: -10.0889
scan:
	Number of images: 20
	           Slice: -30.0000 - 10.0000
	     Image width: 2.0000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 90.0000
	             XTD: 42.3300
	          2theta: -10.0889
scan:
	Number of images: 20
	           Slice: -30.0000 - 10.0000
	     Image width: 2.0000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 180.0000
	             XTD: 42.3300
	          2theta: -10.0889
scan:
	Number of images: 20
	           Slice: -30.0000 - 10.0000
	     Image width: 2.0000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 270.0000
	             XTD: 42.3300
	          2theta: -10.0889

;
_diffrn_measurement_device_details 
;
AFC7: Eulerian 3-circle
;
_diffrn_orient_matrix_UB_11      -0.0187
_diffrn_orient_matrix_UB_12      -0.0706
_diffrn_orient_matrix_UB_13      -0.0010
_diffrn_orient_matrix_UB_21      0.0929
_diffrn_orient_matrix_UB_22      -0.0243
_diffrn_orient_matrix_UB_23      -0.0214
_diffrn_orient_matrix_UB_31      0.0051
_diffrn_orient_matrix_UB_32      -0.0277
_diffrn_orient_matrix_UB_33      0.0533
_diffrn_orient_matrix_type       d*Trek

_diffrn_reflns_number            21935
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.486
_diffrn_reflns_theta_max         27.735
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.794
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.794
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.794
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             4737
_reflns_number_gt                4124
_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.

 Structure factors included contributions from the .fab file.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'Superflip (Palatinus & Chupias, 2007)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'DIAMOND Brandenburg (2007)'
_computing_publication_material  
'PLATON (Spek, 2003) and publCIF (Westrip, 2010)'

_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)+(0.0334P)²+2.6624P] 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         4737
_refine_ls_number_parameters     336
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0788
_refine_ls_wR_factor_gt          0.0731
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.047
_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 0.11150(2) 0.27736(3) 0.23655(2) 0.02700(10) Uani 1 1 d . . . . .
Zn2 Zn -0.15583(2) 1.05025(3) 0.04666(2) 0.02265(9) Uani 1 1 d . . . . .
C1 C 0.17467(19) 0.6650(3) 0.20190(15) 0.0255(6) Uani 1 1 d . . . . .
H1 H 0.2385 0.7064 0.2163 0.031 Uiso 1 1 calc R U . . .
C2 C 0.10889(18) 0.7402(3) 0.23557(14) 0.0242(5) Uani 1 1 d . . . . .
H2 H 0.1308 0.8318 0.2465 0.029 Uiso 1 1 calc R U . . .
C3 C 0.02346(18) 0.7310(2) 0.15121(14) 0.0218(5) Uani 1 1 d . . . . .
H3 H -0.0121 0.6493 0.1492 0.026 Uiso 1 1 calc R U . . .
C4 C 0.09852(19) 0.7023(2) 0.11489(15) 0.0244(5) Uani 1 1 d . . . . .
H4 H 0.0800 0.6272 0.0778 0.029 Uiso 1 1 calc R U . . .
C5 C 0.1812(2) 0.5185(3) 0.21858(16) 0.0316(6) Uani 1 1 d . . . . .
C6 C 0.09737(19) 0.6846(2) 0.30745(15) 0.0246(5) Uani 1 1 d . . . . .
C7 C -0.04941(19) 0.8407(2) 0.12414(15) 0.0251(6) Uani 1 1 d . . . . .
C8 C -0.13045(19) 1.1793(3) -0.08132(15) 0.0267(6) Uani 1 1 d . . . . .
O1 O 0.09923(16) 0.45599(18) 0.19243(12) 0.0382(5) Uani 1 1 d . . . . .
O2 O 0.26031(17) 0.4651(2) 0.25612(14) 0.0503(6) Uani 1 1 d . . . . .
O3 O 0.01465(14) 0.67915(19) 0.30960(11) 0.0338(4) Uani 1 1 d . . . . .
O4 O -0.17405(13) 1.14528(18) 0.13505(10) 0.0283(4) Uani 1 1 d . . . . .
O5 O -0.05619(14) 0.91217(19) 0.06528(11) 0.0323(4) Uani 1 1 d . . . . .
O6 O 0.10395(14) 0.35693(19) 0.33976(11) 0.0332(4) Uani 1 1 d . . . . .
O7 O -0.11794(17) 1.19105(19) -0.00752(12) 0.0411(5) Uani 1 1 d . . . . .
O8 O -0.16755(17) 1.0822(2) -0.12343(13) 0.0448(5) Uani 1 1 d . . . . .
N1 N 0.22348(16) 0.1531(2) 0.29592(14) 0.0315(5) Uani 1 1 d . . . . .
C9 C 0.3050(2) 0.1506(4) 0.2833(2) 0.0533(9) Uani 1 1 d . . . . .
H9 H 0.3112 0.2099 0.2467 0.064 Uiso 1 1 calc R U . . .
C10 C 0.3802(3) 0.0640(4) 0.3221(3) 0.0631(11) Uani 1 1 d . . . . .
H10 H 0.4356 0.0656 0.3114 0.076 Uiso 1 1 calc R U . . .
C11 C 0.3735(2) -0.0253(3) 0.3770(2) 0.0504(9) Uani 1 1 d . . . . .
C12 C 0.2891(3) -0.0233(4) 0.3885(3) 0.0648(11) Uani 1 1 d . . . . .
H12 H 0.2803 -0.0826 0.4238 0.078 Uiso 1 1 calc R U . . .
C13 C 0.2168(3) 0.0667(3) 0.3477(2) 0.0532(9) Uani 1 1 d . . . . .
H13 H 0.1605 0.0664 0.3571 0.064 Uiso 1 1 calc R U . . .
N2 N 0.70864(17) -0.4691(2) 0.49390(14) 0.0322(5) Uani 1 1 d . . . . .
C14 C 0.6649(2) -0.4293(3) 0.54078(19) 0.0412(7) Uani 1 1 d . . . . .
H14 H 0.6951 -0.4462 0.5958 0.049 Uiso 1 1 calc R U . . .
C15 C 0.5767(2) -0.3642(3) 0.5108(2) 0.0512(9) Uani 1 1 d . . . . .
H15 H 0.5484 -0.3384 0.5454 0.061 Uiso 1 1 calc R U . . .
C16 C 0.5300(2) -0.3371(3) 0.4291(2) 0.0482(8) Uani 1 1 d . . . . .
C17 C 0.5746(3) -0.3801(4) 0.3817(2) 0.0688(12) Uani 1 1 d . . . . .
H17 H 0.5451 -0.3660 0.3263 0.083 Uiso 1 1 calc R U . . .
C18 C 0.6629(3) -0.4442(4) 0.4151(2) 0.0558(10) Uani 1 1 d . . . . .
H18 H 0.6920 -0.4713 0.3813 0.067 Uiso 1 1 calc R U . . .
C19 C 0.4563(3) -0.1199(4) 0.4213(3) 0.0731(13) Uani 1 1 d . . . . .
H19A H 0.5141 -0.0903 0.4150 0.088 Uiso 1 1 calc R U . . .
H19B H 0.4704 -0.1169 0.4783 0.088 Uiso 1 1 calc R U . . .
C20 C 0.4363(3) -0.2574(4) 0.3936(3) 0.0652(11) Uani 1 1 d . . . . .
H20A H 0.4102 -0.2603 0.3352 0.078 Uiso 1 1 calc R U . . .
H20B H 0.3882 -0.2947 0.4103 0.078 Uiso 1 1 calc R U . . .
O1W O 0.2115(3) 0.1295(4) 0.5440(3) 0.1084(12) Uani 1 1 d D . . . .
H1A H 0.170(4) 0.073(6) 0.517(4) 0.163 Uiso 1 1 d D U . . .
H1B H 0.190(5) 0.169(6) 0.573(4) 0.163 Uiso 1 1 d D U . . .
O2W O 0.1157(2) 0.1960(3) 0.11665(15) 0.0475(6) Uani 1 1 d D . . . .
H2A H 0.066(3) 0.208(7) 0.075(2) 0.16(3) Uiso 1 1 d D . . . .
H2B H 0.140(4) 0.122(3) 0.118(4) 0.14(2) Uiso 1 1 d D . . . .
O3W O 0.0885(2) 0.9410(3) 0.43797(16) 0.0605(7) Uani 1 1 d D . . . .
H3A H 0.105(3) 0.863(3) 0.457(3) 0.091 Uiso 1 1 d D U . . .
H3B H 0.0290(17) 0.944(5) 0.404(2) 0.091 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 1.9631(19) . y
Zn1 O3 1.9967(19) 2_545 y
Zn1 N1 2.025(2) . y
Zn1 O6 2.0902(18) . y
Zn1 O2W 2.358(2) . y
Zn2 O7 1.9505(19) . y
Zn2 O5 1.9770(19) . y
Zn2 O4 1.9891(17) . y
Zn2 N2 2.035(2) 4_465 y
C1 C5 1.514(4) . ?
C1 C2 1.560(3) . ?
C1 C4 1.572(3) . ?
C1 H1 0.9800 . ?
C2 C6 1.499(3) . ?
C2 C3 1.547(3) . ?
C2 H2 0.9800 . ?
C3 C7 1.497(4) . ?
C3 C4 1.551(3) . ?
C3 H3 0.9800 . ?
C4 C8 1.514(3) 3_575 ?
C4 H4 0.9800 . ?
C5 O2 1.228(3) . y
C5 O1 1.291(4) . y
C6 O3 1.261(3) . y
C6 O4 1.262(3) 2_545 y
C7 O6 1.254(3) 2 y
C7 O5 1.263(3) . y
C8 O8 1.233(3) . y
C8 O7 1.283(3) . y
C8 C4 1.514(3) 3_575 ?
O3 Zn1 1.9967(19) 2 ?
O4 C6 1.262(3) 2 ?
O6 C7 1.254(3) 2_545 ?
N1 C13 1.321(4) . ?
N1 C9 1.335(4) . ?
C9 C10 1.377(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(5) . ?
C11 C19 1.515(4) . ?
C12 C13 1.379(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
N2 C14 1.336(4) . ?
N2 C18 1.336(4) . ?
N2 Zn2 2.035(2) 4_666 ?
C14 C15 1.378(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.364(5) . ?
C16 C20 1.519(4) . ?
C17 C18 1.375(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.473(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
O1W H1A 0.84(2) . ?
O1W H1B 0.84(2) . ?
O2W H2A 0.83(2) . ?
O2W H2B 0.84(2) . ?
O3W H3A 0.861(19) . ?
O3W H3B 0.854(19) . ?

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 112.14(9) . 2_545 y
O1 Zn1 N1 135.49(9) . . y
O3 Zn1 N1 110.47(9) 2_545 . y
O1 Zn1 O6 88.79(8) . . y
O3 Zn1 O6 100.32(7) 2_545 . y
N1 Zn1 O6 95.83(9) . . y
O1 Zn1 O2W 88.84(9) . . y
O3 Zn1 O2W 79.43(8) 2_545 . y
N1 Zn1 O2W 86.74(9) . . y
O6 Zn1 O2W 177.31(9) . . y
O7 Zn2 O5 104.48(8) . . y
O7 Zn2 O4 102.59(8) . . y
O5 Zn2 O4 123.50(8) . . y
O7 Zn2 N2 120.13(10) . 4_465 y
O5 Zn2 N2 109.48(9) . 4_465 y
O4 Zn2 N2 97.77(8) . 4_465 y
C5 C1 C2 113.7(2) . . ?
C5 C1 C4 113.6(2) . . ?
C2 C1 C4 87.75(18) . . ?
C5 C1 H1 113.1 . . ?
C2 C1 H1 113.1 . . ?
C4 C1 H1 113.1 . . ?
C6 C2 C3 119.8(2) . . ?
C6 C2 C1 118.5(2) . . ?
C3 C2 C1 88.96(18) . . ?
C6 C2 H2 109.3 . . ?
C3 C2 H2 109.3 . . ?
C1 C2 H2 109.3 . . ?
C7 C3 C2 118.6(2) . . ?
C7 C3 C4 124.2(2) . . ?
C2 C3 C4 88.98(18) . . ?
C7 C3 H3 107.8 . . ?
C2 C3 H3 107.8 . . ?
C4 C3 H3 107.8 . . ?
C8 C4 C3 115.4(2) 3_575 . ?
C8 C4 C1 112.2(2) 3_575 . ?
C3 C4 C1 88.40(18) . . ?
C8 C4 H4 112.9 3_575 . ?
C3 C4 H4 112.9 . . ?
C1 C4 H4 112.9 . . ?
O2 C5 O1 123.1(3) . . ?
O2 C5 C1 121.0(3) . . ?
O1 C5 C1 115.9(2) . . ?
O3 C6 O4 122.5(2) . 2_545 ?
O3 C6 C2 120.8(2) . . ?
O4 C6 C2 116.7(2) 2_545 . ?
O6 C7 O5 121.7(2) 2 . ?
O6 C7 C3 118.2(2) 2 . ?
O5 C7 C3 120.1(2) . . ?
O8 C8 O7 124.0(2) . . ?
O8 C8 C4 121.5(2) . 3_575 ?
O7 C8 C4 114.4(2) . 3_575 ?
C5 O1 Zn1 112.93(18) . . ?
C6 O3 Zn1 137.95(17) . 2 ?
C6 O4 Zn2 116.27(17) 2 . ?
C7 O5 Zn2 110.21(17) . . ?
C7 O6 Zn1 135.07(17) 2_545 . ?
C8 O7 Zn2 120.86(18) . . ?
C13 N1 C9 117.0(3) . . ?
C13 N1 Zn1 120.4(2) . . ?
C9 N1 Zn1 122.6(2) . . ?
N1 C9 C10 122.7(3) . . ?
N1 C9 H9 118.6 . . ?
C10 C9 H9 118.6 . . ?
C9 C10 C11 120.2(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 116.5(3) . . ?
C12 C11 C19 122.6(4) . . ?
C10 C11 C19 120.9(4) . . ?
C11 C12 C13 120.2(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
N1 C13 C12 123.4(3) . . ?
N1 C13 H13 118.3 . . ?
C12 C13 H13 118.3 . . ?
C14 N2 C18 117.2(3) . . ?
C14 N2 Zn2 118.74(19) . 4_666 ?
C18 N2 Zn2 123.9(2) . 4_666 ?
N2 C14 C15 122.5(3) . . ?
N2 C14 H14 118.7 . . ?
C15 C14 H14 118.7 . . ?
C14 C15 C16 120.1(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 116.7(3) . . ?
C17 C16 C20 120.9(3) . . ?
C15 C16 C20 122.3(3) . . ?
C16 C17 C18 120.6(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
N2 C18 C17 122.8(3) . . ?
N2 C18 H18 118.6 . . ?
C17 C18 H18 118.6 . . ?
C20 C19 C11 114.4(3) . . ?
C20 C19 H19A 108.7 . . ?
C11 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
C11 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C19 C20 C16 109.8(3) . . ?
C19 C20 H20A 109.7 . . ?
C16 C20 H20A 109.7 . . ?
C19 C20 H20B 109.7 . . ?
C16 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
H1A O1W H1B 108(7) . . ?
Zn1 O2W H2A 117(5) . . ?
Zn1 O2W H2B 117(4) . . ?
H2A O2W H2B 113(6) . . ?
H3A O3W H3B 112(4) . . ?

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
C5 C1 C2 C6 27.1(3) . . . . ?
C4 C1 C2 C6 141.9(2) . . . . ?
C5 C1 C2 C3 -96.6(2) . . . . ?
C4 C1 C2 C3 18.17(18) . . . . ?
C6 C2 C3 C7 90.0(3) . . . . ?
C1 C2 C3 C7 -147.4(2) . . . . ?
C6 C2 C3 C4 -141.0(2) . . . . ?
C1 C2 C3 C4 -18.42(18) . . . . ?
C7 C3 C4 C8 28.8(3) . . . 3_575 ?
C2 C3 C4 C8 -95.6(2) . . . 3_575 ?
C7 C3 C4 C1 142.7(2) . . . . ?
C2 C3 C4 C1 18.27(19) . . . . ?
C5 C1 C4 C8 -146.3(2) . . . 3_575 ?
C2 C1 C4 C8 98.7(2) . . . 3_575 ?
C5 C1 C4 C3 96.9(2) . . . . ?
C2 C1 C4 C3 -18.13(18) . . . . ?
C2 C1 C5 O2 -122.0(3) . . . . ?
C4 C1 C5 O2 139.7(3) . . . . ?
C2 C1 C5 O1 56.7(3) . . . . ?
C4 C1 C5 O1 -41.6(3) . . . . ?
C3 C2 C6 O3 -28.8(4) . . . . ?
C1 C2 C6 O3 -135.4(3) . . . . ?
C3 C2 C6 O4 151.8(2) . . . 2_545 ?
C1 C2 C6 O4 45.1(3) . . . 2_545 ?
C2 C3 C7 O6 -67.2(3) . . . 2 ?
C4 C3 C7 O6 -177.4(2) . . . 2 ?
C2 C3 C7 O5 114.2(3) . . . . ?
C4 C3 C7 O5 4.1(4) . . . . ?
O2 C5 O1 Zn1 11.3(3) . . . . ?
C1 C5 O1 Zn1 -167.38(17) . . . . ?
O4 C6 O3 Zn1 151.1(2) 2_545 . . 2 ?
C2 C6 O3 Zn1 -28.4(4) . . . 2 ?
O6 C7 O5 Zn2 3.1(3) 2 . . . ?
C3 C7 O5 Zn2 -178.40(18) . . . . ?
O8 C8 O7 Zn2 1.1(4) . . . . ?
C4 C8 O7 Zn2 179.26(17) 3_575 . . . ?
C13 N1 C9 C10 -0.6(5) . . . . ?
Zn1 N1 C9 C10 -178.4(3) . . . . ?
N1 C9 C10 C11 -0.1(6) . . . . ?
C9 C10 C11 C12 1.1(6) . . . . ?
C9 C10 C11 C19 -179.1(4) . . . . ?
C10 C11 C12 C13 -1.4(6) . . . . ?
C19 C11 C12 C13 178.8(4) . . . . ?
C9 N1 C13 C12 0.3(6) . . . . ?
Zn1 N1 C13 C12 178.1(3) . . . . ?
C11 C12 C13 N1 0.7(7) . . . . ?
C18 N2 C14 C15 -0.5(5) . . . . ?
Zn2 N2 C14 C15 174.8(3) 4_666 . . . ?
N2 C14 C15 C16 -0.3(5) . . . . ?
C14 C15 C16 C17 1.3(5) . . . . ?
C14 C15 C16 C20 -175.6(3) . . . . ?
C15 C16 C17 C18 -1.6(6) . . . . ?
C20 C16 C17 C18 175.4(4) . . . . ?
C14 N2 C18 C17 0.2(6) . . . . ?
Zn2 N2 C18 C17 -174.9(3) 4_666 . . . ?
C16 C17 C18 N2 0.9(7) . . . . ?
C12 C11 C19 C20 72.8(6) . . . . ?
C10 C11 C19 C20 -107.0(5) . . . . ?
C11 C19 C20 C16 168.3(4) . . . . y
C17 C16 C20 C19 -109.0(5) . . . . ?
C15 C16 C20 C19 67.8(5) . . . . ?

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
O1W H1B O2W 0.84(2) 2.11(3) 2.921(4) 163(7) 4_566
O2W H2B O8 0.84(2) 2.11(2) 2.922(4) 165(6) 3_565
O3W H3A O7 0.861(19) 1.95(2) 2.792(3) 167(4) 2_545
O3W H3B O1 0.854(19) 2.01(2) 2.848(4) 169(5) 2

_refine_diff_density_max         0.360
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.076

_shelxl_version_number           2013-3



loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?

####################################################################### 
# 
# 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_CD03212
_database_code_depnum_ccdc_archive 'CCDC 1004888'
#Added by publCIF



_audit_update_record             
;
2014-05-22 deposited with the CCDC.
2015-06-22 downloaded from the CCDC.
;
_publcif_datablock.id            {0ff1f51e-6401-4ada-91c0-620cab0633f8}

_cell_special_details            ?
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 N O5 Zn'
_chemical_formula_sum            'C10 H10 N O5 Zn'
_chemical_formula_weight         289.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Zn Zn 0.2839 1.4301 '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'
C C 0.0033 0.0016 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 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, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   5.8438(13)
_cell_length_b                   12.088(3)
_cell_length_c                   15.288(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.975(5)
_cell_angle_gamma                90
_cell_volume                     1063.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6773
_cell_measurement_theta_min      1.6863
_cell_measurement_theta_max      28.1952

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_F_000             588
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.37
_exptl_absorpt_coefficient_mu    2.318
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.370
_exptl_absorpt_correction_T_max  0.434
_exptl_absorpt_process_details   'Jacobson, R. (1998), Private communication'


_exptl_special_details           ?

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  
;
Mercury (2x2 bin mode)
;
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 14.6306
_diffrn_reflns_number            12846
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.685
_diffrn_reflns_theta_max         28.173
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.809
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.809
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.809
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             2115
_reflns_number_gt                1760

_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_measurement_details      
;
scan:
	Number of images: 180
	           Slice: 0.0000 - 360.0000
	     Image width: 2.0000
	        Exp time: 150.0000
	   Rotation axis: Phi
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 0.0000
	             XTD: 40.9756
	          2theta: -10.2309
scan:
	Number of images: 17
	           Slice: -24.0000 - 10.0000
	     Image width: 2.0000
	        Exp time: 150.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 0.0000
	             XTD: 40.9756
	          2theta: -10.2309
scan:
	Number of images: 20
	           Slice: -30.0000 - 10.0000
	     Image width: 2.0000
	        Exp time: 150.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 90.0000
	             XTD: 40.9756
	          2theta: -10.2309
scan:
	Number of images: 20
	           Slice: -30.0000 - 10.0000
	     Image width: 2.0000
	        Exp time: 150.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 180.0000
	             XTD: 40.9756
	          2theta: -10.2309
scan:
	Number of images: 20
	           Slice: -30.0000 - 10.0000
	     Image width: 2.0000
	        Exp time: 150.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 270.0000
	             XTD: 40.9756
	          2theta: -10.2309

;
_diffrn_measurement_device_details 
;
AFC7: Eulerian 3-circle
;
_diffrn_orient_matrix_UB_11      -0.0029
_diffrn_orient_matrix_UB_12      -0.1163
_diffrn_orient_matrix_UB_13      0.1293
_diffrn_orient_matrix_UB_21      0.0051
_diffrn_orient_matrix_UB_22      0.0614
_diffrn_orient_matrix_UB_23      0.0553
_diffrn_orient_matrix_UB_31      -0.0655
_diffrn_orient_matrix_UB_32      -0.0040
_diffrn_orient_matrix_UB_33      0.0104
_diffrn_orient_matrix_type       d*Trek


_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       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  
'SHELXL-2013 (Sheldrick, 2013), SHELXLE (Hubschle, Sheldrick & Dittrich, 2011)'
_computing_molecular_graphics    'DIAMOND Brandenburg (2007)'
_computing_publication_material  
'PLATON (Spek, 2003) and publCIF (Westrip, 2010)'

_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)+(0.0435P)²+0.7088P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     vecmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2115
_refine_ls_number_parameters     160
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.102
_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 0.67856(6) 0.33701(3) 0.47405(2) 0.02376(14) Uani 1 1 d . . . . .
N1 N 0.5996(5) 0.1838(2) 0.42714(17) 0.0293(6) Uani 1 1 d . . . . .
C1 C 0.7545(6) 0.1022(3) 0.4339(2) 0.0423(9) Uani 1 1 d . . . . .
H1 H 0.9012 0.1145 0.4671 0.051 Uiso 1 1 calc R U . . .
C2 C 0.7088(7) 0.0014(3) 0.3944(2) 0.0451(10) Uani 1 1 d . . . . .
H2 H 0.8228 -0.0531 0.4014 0.054 Uiso 1 1 calc R U . . .
C3 C 0.4933(6) -0.0196(3) 0.3440(2) 0.0342(8) Uani 1 1 d . . . . .
C4 C 0.3321(7) 0.0643(3) 0.3395(3) 0.0511(11) Uani 1 1 d . . . . .
H4 H 0.1823 0.0535 0.3084 0.061 Uiso 1 1 calc R U . . .
C5 C 0.3912(7) 0.1633(3) 0.3804(3) 0.0478(10) Uani 1 1 d . . . . .
H5 H 0.2798 0.2189 0.3752 0.057 Uiso 1 1 calc R U . . .
C6 C 0.4417(7) -0.1248(3) 0.2917(2) 0.0367(8) Uani 1 1 d . . . . .
H6A H 0.2750 -0.1327 0.2738 0.044 Uiso 1 1 calc R U . . .
H6B H 0.4977 -0.1875 0.3289 0.044 Uiso 1 1 calc R U . . .
C7 C 1.0933(5) 0.3741(3) 0.71837(18) 0.0224(6) Uani 1 1 d . . . . .
H7 H 1.2354 0.3339 0.7432 0.027 Uiso 1 1 calc R U . . .
C8 C 0.8848(5) 0.4994(2) 0.26738(17) 0.0197(6) Uani 1 1 d . . . . .
H8 H 0.7585 0.4848 0.2176 0.024 Uiso 1 1 calc R U . . .
C9 C 0.8500(5) 0.4282(2) 0.34458(18) 0.0218(6) Uani 1 1 d . . . . .
C10 C 0.9812(6) 0.3319(3) 0.6283(2) 0.0262(7) Uani 1 1 d . . . . .
O1 O 0.6663(4) 0.44944(18) 0.37768(13) 0.0267(5) Uani 1 1 d . . . . .
O2 O 0.9838(4) 0.35197(18) 0.37334(14) 0.0301(5) Uani 1 1 d . . . . .
O3 O 0.9903(5) 0.2329(2) 0.61066(16) 0.0475(7) Uani 1 1 d . . . . .
O4 O 0.8667(4) 0.4031(2) 0.57687(13) 0.0337(5) Uani 1 1 d . . . . .
O1W O 0.3667(4) 0.3717(2) 0.51143(15) 0.0335(5) Uani 1 1 d D . . . .
H1W H 0.371(7) 0.423(3) 0.550(2) 0.050 Uiso 1 1 d D U . . .
H2W H 0.248(5) 0.381(4) 0.472(2) 0.050 Uiso 1 1 d D 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 O4 1.929(2) . y
Zn1 O1 1.997(2) . y
Zn1 N1 2.011(3) . y
Zn1 O1W 2.045(2) . y
N1 C5 1.324(4) . ?
N1 C1 1.331(4) . ?
C1 C2 1.366(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.381(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(5) . ?
C3 C6 1.505(4) . ?
C4 C5 1.368(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C6 1.545(7) 2_655 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C10 1.507(4) . ?
C7 C8 1.547(4) 3_766 ?
C7 C7 1.578(6) 2_756 ?
C7 H7 0.9800 . ?
C8 C9 1.503(4) . ?
C8 C8 1.531(6) 2_755 ?
C8 C7 1.547(4) 3_766 ?
C8 H8 0.9800 . ?
C9 O2 1.239(4) . ?
C9 O1 1.290(3) . ?
C10 O3 1.231(4) . ?
C10 O4 1.275(4) . ?
O1W H1W 0.850(19) . ?
O1W H2W 0.848(19) . ?

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
O4 Zn1 O1 105.19(10) . . y
O4 Zn1 N1 137.36(11) . . y
O1 Zn1 N1 112.77(10) . . y
O4 Zn1 O1W 95.57(10) . . y
O1 Zn1 O1W 98.43(10) . . y
N1 Zn1 O1W 97.36(11) . . y
C5 N1 C1 116.9(3) . . ?
C5 N1 Zn1 119.8(2) . . ?
C1 N1 Zn1 123.0(2) . . ?
N1 C1 C2 123.3(3) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C1 C2 C3 120.0(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 116.2(3) . . ?
C4 C3 C6 121.5(3) . . ?
C2 C3 C6 122.1(3) . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
N1 C5 C4 123.1(3) . . ?
N1 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
C3 C6 C6 111.2(2) . 2_655 ?
C3 C6 H6A 109.4 . . ?
C6 C6 H6A 109.4 2_655 . ?
C3 C6 H6B 109.4 . . ?
C6 C6 H6B 109.4 2_655 . ?
H6A C6 H6B 108.0 . . ?
C10 C7 C8 118.4(2) . 3_766 ?
C10 C7 C7 108.8(3) . 2_756 ?
C8 C7 C7 87.87(14) 3_766 2_756 ?
C10 C7 H7 113.1 . . ?
C8 C7 H7 113.1 3_766 . ?
C7 C7 H7 113.1 2_756 . ?
C9 C8 C8 121.3(2) . 2_755 ?
C9 C8 C7 118.4(2) . 3_766 ?
C8 C8 C7 89.58(15) 2_755 3_766 ?
C9 C8 H8 108.7 . . ?
C8 C8 H8 108.7 2_755 . ?
C7 C8 H8 108.7 3_766 . ?
O2 C9 O1 121.8(3) . . ?
O2 C9 C8 122.8(3) . . ?
O1 C9 C8 115.4(3) . . ?
O3 C10 O4 124.0(3) . . ?
O3 C10 C7 120.1(3) . . ?
O4 C10 C7 115.7(3) . . ?
C9 O1 Zn1 103.17(18) . . ?
C10 O4 Zn1 112.8(2) . . ?
Zn1 O1W H1W 115(3) . . ?
Zn1 O1W H2W 119(3) . . ?
H1W O1W H2W 109(4) . . ?

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
C5 N1 C1 C2 1.0(6) . . . . ?
Zn1 N1 C1 C2 -173.1(3) . . . . ?
N1 C1 C2 C3 0.4(6) . . . . ?
C1 C2 C3 C4 -2.2(6) . . . . ?
C1 C2 C3 C6 173.7(4) . . . . ?
C2 C3 C4 C5 2.6(6) . . . . ?
C6 C3 C4 C5 -173.3(4) . . . . ?
C1 N1 C5 C4 -0.5(6) . . . . ?
Zn1 N1 C5 C4 173.7(4) . . . . ?
C3 C4 C5 N1 -1.3(7) . . . . ?
C3 C6 C6 C3 -49.9(6) . . 2_655 2_655 y
C4 C3 C6 C6 102.0(5) . . . 2_655 ?
C2 C3 C6 C6 -73.7(5) . . . 2_655 ?
C8 C8 C9 O2 -13.8(4) 2_755 . . . ?
C7 C8 C9 O2 -122.4(3) 3_766 . . . ?
C8 C8 C9 O1 168.2(2) 2_755 . . . ?
C7 C8 C9 O1 59.6(3) 3_766 . . . ?
C8 C7 C10 O3 169.6(3) 3_766 . . . ?
C7 C7 C10 O3 -92.4(3) 2_756 . . . ?
C8 C7 C10 O4 -15.2(4) 3_766 . . . ?
C7 C7 C10 O4 82.8(3) 2_756 . . . ?
O2 C9 O1 Zn1 0.5(3) . . . . ?
C8 C9 O1 Zn1 178.51(19) . . . . ?
O3 C10 O4 Zn1 6.9(4) . . . . ?
C7 C10 O4 Zn1 -168.07(19) . . . . ?

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
O1W H1W O1 0.850(19) 1.93(2) 2.775(3) 170(4) 3_666
O1W H2W O2 0.848(19) 1.99(2) 2.808(3) 162(4) 1_455

_refine_diff_density_max         0.326
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.099

_shelxl_version_number           2013-3


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?
####################################################################### 
# 
# 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_cd09610_001_sq
_database_code_depnum_ccdc_archive 'CCDC 1028267'
#Added by publCIF



_audit_update_record             
;
2014-10-08 deposited with the CCDC.
2015-06-22 downloaded from the CCDC.
;
_publcif_datablock.id            {b5506f9b-d370-4c9d-8ca8-84c666f43d8f}
# publcif _publ_body_element loop end


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 N2 Ni O7, H2 O'
_chemical_formula_sum            'C16 H22 N2 Ni O8'
_chemical_formula_weight         429.06

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'
Ni Ni 0.3393 1.1124 '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           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 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, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   12.956(2)
_cell_length_b                   9.8991(10)
_cell_length_c                   16.960(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.750(2)
_cell_angle_gamma                90
_cell_volume                     2047.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    13158
_cell_measurement_theta_min      1.6702
_cell_measurement_theta_max      27.6002

_exptl_crystal_description       block
_exptl_crystal_colour            'light blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.990
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.700
_exptl_absorpt_correction_T_max  0.800
_exptl_absorpt_process_details   'Jacobson, R. (1998), Private communication'

_exptl_special_details           ?

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       'Mercury CCD'
_diffrn_measurement_device_type  'Rigaku, AFC-7 diffractometer'
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 14.6306
_diffrn_reflns_number            23825
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.057
_diffrn_reflns_theta_max         27.642
_diffrn_reflns_theta_full        25.241


_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_measurement_details      
;
scan:
	Number of images: 180
	           Slice: 0.0000 - 360.0000
	     Image width: 2.0000
	        Exp time: 90.0000
	   Rotation axis: Phi
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 0.0000
	             XTD: 42.2802
	          2theta: -10.0862
scan:
	Number of images: 17
	           Slice: -24.0000 - 10.0000
	     Image width: 2.0000
	        Exp time: 90.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 0.0000
	             XTD: 42.2802
	          2theta: -10.0862
scan:
	Number of images: 20
	           Slice: -30.0000 - 10.0000
	     Image width: 2.0000
	        Exp time: 90.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 90.0000
	             XTD: 42.2802
	          2theta: -10.0862
scan:
	Number of images: 20
	           Slice: -30.0000 - 10.0000
	     Image width: 2.0000
	        Exp time: 90.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 180.0000
	             XTD: 42.2802
	          2theta: -10.0862
scan:
	Number of images: 20
	           Slice: -30.0000 - 10.0000
	     Image width: 2.0000
	        Exp time: 90.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 270.0000
	             XTD: 42.2802
	          2theta: -10.0862

;
_diffrn_measurement_device_details 
;
AFC7: Eulerian 3-circle
;

_diffrn_measured_fraction_theta_max 0.813
_diffrn_measured_fraction_theta_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.813
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.813
_diffrn_reflns_point_group_measured_fraction_full 0.957
_reflns_number_total             3874
_reflns_number_gt                3289
_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.

 Structure factors included contributions from the .fab file.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  
'SHELXL-2013 (Sheldrick, 2013), SHELXLE (Hubschle, Sheldrick & Dittrich, 2011)'
_computing_molecular_graphics    'DIAMOND Brandenburg (2007)'
_computing_publication_material  
'PLATON (Spek, 2003) and publCIF (Westrip, 2010)'


_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0396P)²+1.2083P] 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         3874
_refine_ls_number_parameters     268
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0879
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.060
_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
Ni1 Ni 0.16320(2) 0.24011(3) 0.54163(2) 0.02554(10) Uani 1 1 d . . . . .
O1 O 0.10126(12) 0.23314(14) 0.41233(9) 0.0275(3) Uani 1 1 d . . . . .
O2 O 0.02443(14) 0.02887(15) 0.38862(9) 0.0380(4) Uani 1 1 d . . . . .
O3 O 0.02063(13) 0.52667(15) 0.36548(9) 0.0379(4) Uani 1 1 d . . . . .
O4 O -0.11319(13) 0.39491(16) 0.37773(9) 0.0364(4) Uani 1 1 d . . . . .
N1 N 0.32062(15) 0.2133(2) 0.53878(11) 0.0333(4) Uani 1 1 d . . . . .
N2 N 0.79256(15) 0.26406(18) 0.82919(11) 0.0308(4) Uani 1 1 d . . . . .
C1 C -0.03515(16) 0.1924(2) 0.27979(11) 0.0250(4) Uani 1 1 d . . . . .
H1 H -0.1044 0.1427 0.2572 0.030 Uiso 1 1 calc R U . . .
C2 C -0.04791(17) 0.3476(2) 0.26685(12) 0.0262(4) Uani 1 1 d . . . . .
H2 H -0.1161 0.3666 0.2207 0.031 Uiso 1 1 calc R U . . .
C3 C -0.04504(18) 0.4309(2) 0.34201(12) 0.0295(5) Uani 1 1 d . . . . .
C4 C 0.03431(17) 0.1481(2) 0.36690(12) 0.0259(4) Uani 1 1 d . . . . .
C5 C 0.3469(2) 0.2702(3) 0.47669(16) 0.0451(6) Uani 1 1 d . . . . .
H5 H 0.2937 0.3201 0.4366 0.054 Uiso 1 1 calc R U . . .
C6 C 0.4488(2) 0.2586(3) 0.46909(16) 0.0467(7) Uani 1 1 d . . . . .
H6 H 0.4635 0.3015 0.4253 0.056 Uiso 1 1 calc R U . . .
C7 C 0.52936(18) 0.1831(3) 0.52652(14) 0.0386(5) Uani 1 1 d . . . . .
C8 C 0.50171(19) 0.1221(3) 0.58975(14) 0.0410(6) Uani 1 1 d . . . . .
H8 H 0.5530 0.0695 0.6296 0.049 Uiso 1 1 calc R U . . .
C9 C 0.39797(18) 0.1391(2) 0.59396(14) 0.0370(5) Uani 1 1 d . . . . .
H9 H 0.3811 0.0970 0.6371 0.044 Uiso 1 1 calc R U . . .
C10 C 0.85074(19) 0.2005(3) 0.78835(13) 0.0385(5) Uani 1 1 d . . . . .
H10 H 0.9090 0.1461 0.8191 0.046 Uiso 1 1 calc R U . . .
C11 C 0.8289(2) 0.2114(3) 0.70359(14) 0.0410(6) Uani 1 1 d . . . . .
H11 H 0.8715 0.1647 0.6782 0.049 Uiso 1 1 calc R U . . .
C12 C 0.74310(19) 0.2921(3) 0.65578(14) 0.0361(5) Uani 1 1 d . . . . .
C13 C 0.6849(2) 0.3606(3) 0.69823(14) 0.0419(6) Uani 1 1 d . . . . .
H13 H 0.6278 0.4178 0.6692 0.050 Uiso 1 1 calc R U . . .
C14 C 0.71128(19) 0.3443(2) 0.78334(14) 0.0390(5) Uani 1 1 d . . . . .
H14 H 0.6707 0.3912 0.8103 0.047 Uiso 1 1 calc R U . . .
C15 C 0.6424(2) 0.1741(3) 0.52055(16) 0.0478(7) Uani 1 1 d . . . . .
H15A H 0.6365 0.1701 0.4620 0.057 Uiso 1 1 calc R U . . .
H15B H 0.6774 0.0916 0.5474 0.057 Uiso 1 1 calc R U . . .
C16 C 0.7141(2) 0.2959(3) 0.56234(15) 0.0477(6) Uani 1 1 d . . . . .
H16A H 0.7808 0.2953 0.5484 0.057 Uiso 1 1 calc R U . . .
H16B H 0.6749 0.3789 0.5408 0.057 Uiso 1 1 calc R U . . .
O1W O 0.17747(13) 0.44535(15) 0.52309(10) 0.0327(3) Uani 1 1 d D . . . .
H1A H 0.1375(19) 0.468(3) 0.4741(12) 0.049 Uiso 1 1 d D U . . .
H1B H 0.154(2) 0.488(3) 0.5571(14) 0.049 Uiso 1 1 d D U . . .
O2W O -0.00056(13) 0.26909(15) 0.53451(10) 0.0306(3) Uani 1 1 d D . . . .
H2A H -0.007(2) 0.330(2) 0.5687(14) 0.046 Uiso 1 1 d D U . . .
H2B H -0.032(2) 0.300(3) 0.4859(12) 0.046 Uiso 1 1 d D U . . .
O3W O 0.14637(13) 0.02904(16) 0.55130(10) 0.0351(4) Uani 1 1 d D . . . .
H3A H 0.116(2) 0.016(3) 0.4978(11) 0.053 Uiso 1 1 d D U . . .
H3B H 0.0968(18) 0.017(3) 0.5719(16) 0.053 Uiso 1 1 d D U . . .
O4W O -0.2797(3) 0.1964(4) 0.3352(2) 0.1062(9) Uani 1 1 d D . . . .
H4A H -0.230(4) 0.256(5) 0.341(4) 0.159 Uiso 1 1 d D U . . .
H4B H -0.305(5) 0.261(5) 0.296(3) 0.159 Uiso 1 1 d D U . . .


_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag

Ni1 O1 2.0660(15) . . yes
Ni1 O1W 2.0737(16) . . yes
Ni1 O2W 2.1036(18) . . yes
Ni1 O3W 2.1129(16) . . yes
Ni1 N1 2.073(2) . . yes
Ni1 N2 2.0823(18) . 2_656 yes
O1 C4 1.266(3) . . no
O2 C4 1.256(2) . . no
O3 C3 1.246(3) . . no
O4 C3 1.279(3) . . no
N1 C5 1.336(3) . . no
N1 C9 1.336(3) . . no
O1W H1A 0.85(2) . . no
O1W H1B 0.85(3) . . no
N2 C10 1.340(3) . . no
N2 C14 1.338(3) . . no
O2W H2A 0.86(2) . . no
O2W H2B 0.84(2) . . no
O3W H3B 0.84(3) . . no
O3W H3A 0.868(18) . . no
C1 C2 1.553(3) . . no
C1 C1 1.573(3) . 2_555 no
C1 C4 1.512(3) . . no
C2 C3 1.508(3) . . no
C2 C2 1.532(3) . 2_555 no
C5 C6 1.374(4) . . no
C6 C7 1.382(4) . . no
C7 C15 1.504(4) . . no
C7 C8 1.379(4) . . no
C8 C9 1.380(4) . . no
C10 C11 1.372(3) . . no
C11 C12 1.386(4) . . no
C12 C13 1.383(4) . . no
C12 C16 1.501(3) . . no
C13 C14 1.376(3) . . no
C15 C16 1.541(4) . . no
C1 H1 0.9800 . . no
C2 H2 0.9800 . . no
O4W H4B 0.90(5) . . no
O4W H4A 0.85(6) . . no
C5 H5 0.9300 . . no
C6 H6 0.9300 . . no
C8 H8 0.9300 . . no
C9 H9 0.9300 . . no
C10 H10 0.9300 . . no
C11 H11 0.9300 . . no
C13 H13 0.9300 . . no
C14 H14 0.9300 . . no
C15 H15A 0.9700 . . no
C15 H15B 0.9700 . . no
C16 H16B 0.9700 . . no
C16 H16A 0.9700 . . no


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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag

O1 Ni1 O1W 83.93(6) . . . yes
O1 Ni1 O2W 85.48(6) . . . yes
O1 Ni1 O3W 92.07(6) . . . yes
O1 Ni1 N1 90.19(7) . . . yes
O1 Ni1 N2 172.17(7) . . 2_656 yes
O1W Ni1 O2W 89.86(6) . . . yes
O1W Ni1 O3W 175.93(6) . . . yes
O1W Ni1 N1 89.03(7) . . . yes
O1W Ni1 N2 92.35(7) . . 2_656 yes
O2W Ni1 O3W 90.62(6) . . . yes
O2W Ni1 N1 175.62(7) . . . yes
O2W Ni1 N2 87.63(7) . . 2_656 yes
O3W Ni1 N1 90.19(7) . . . yes
O3W Ni1 N2 91.71(7) . . 2_656 yes
N1 Ni1 N2 96.66(8) . . 2_656 yes
Ni1 O1 C4 127.49(13) . . . no
Ni1 N1 C5 118.63(17) . . . no
Ni1 N1 C9 124.39(16) . . . no
C5 N1 C9 117.0(2) . . . no
Ni1 O1W H1A 111(2) . . . no
Ni1 O1W H1B 108.3(19) . . . no
H1A O1W H1B 107(2) . . . no
Ni1 N2 C14 124.17(15) 2_656 . . no
Ni1 N2 C10 119.17(15) 2_656 . . no
C10 N2 C14 116.60(19) . . . no
H2A O2W H2B 106(2) . . . no
Ni1 O2W H2B 104.5(18) . . . no
Ni1 O2W H2A 112.5(18) . . . no
Ni1 O3W H3A 95(2) . . . no
Ni1 O3W H3B 107(2) . . . no
H3A O3W H3B 106(2) . . . no
C2 C1 C4 115.14(16) . . . no
C1 C1 C2 88.07(15) 2_555 . . no
C1 C1 C4 110.19(17) 2_555 . . no
C1 C2 C3 116.78(16) . . . no
C2 C2 C3 121.58(18) 2_555 . . no
C1 C2 C2 89.53(16) . . 2_555 no
O4 C3 C2 115.11(18) . . . no
O3 C3 C2 120.4(2) . . . no
O3 C3 O4 124.54(19) . . . no
O1 C4 O2 124.28(18) . . . no
O1 C4 C1 117.45(17) . . . no
O2 C4 C1 118.24(18) . . . no
N1 C5 C6 123.2(2) . . . no
C5 C6 C7 120.0(2) . . . no
C6 C7 C15 120.3(2) . . . no
C8 C7 C15 122.7(2) . . . no
C6 C7 C8 116.9(2) . . . no
C7 C8 C9 120.0(2) . . . no
N1 C9 C8 122.9(2) . . . no
N2 C10 C11 123.5(2) . . . no
C10 C11 C12 119.9(2) . . . no
C13 C12 C16 123.5(2) . . . no
C11 C12 C16 119.8(2) . . . no
C11 C12 C13 116.6(2) . . . no
C12 C13 C14 120.2(2) . . . no
N2 C14 C13 123.2(2) . . . no
C7 C15 C16 111.8(2) . . . no
C12 C16 C15 111.3(2) . . . no
C2 C1 H1 114.00 . . . no
C4 C1 H1 114.00 . . . no
C1 C1 H1 114.00 2_555 . . no
C1 C2 H2 109.00 . . . no
C3 C2 H2 109.00 . . . no
C2 C2 H2 109.00 2_555 . . no
H4A O4W H4B 71(6) . . . no
N1 C5 H5 118.00 . . . no
C6 C5 H5 118.00 . . . no
C5 C6 H6 120.00 . . . no
C7 C6 H6 120.00 . . . no
C9 C8 H8 120.00 . . . no
C7 C8 H8 120.00 . . . no
N1 C9 H9 119.00 . . . no
C8 C9 H9 119.00 . . . no
C11 C10 H10 118.00 . . . no
N2 C10 H10 118.00 . . . no
C10 C11 H11 120.00 . . . no
C12 C11 H11 120.00 . . . no
C14 C13 H13 120.00 . . . no
C12 C13 H13 120.00 . . . no
N2 C14 H14 118.00 . . . no
C13 C14 H14 118.00 . . . no
C7 C15 H15B 109.00 . . . no
C16 C15 H15A 109.00 . . . no
C7 C15 H15A 109.00 . . . no
H15A C15 H15B 108.00 . . . no
C16 C15 H15B 109.00 . . . no
C12 C16 H16A 109.00 . . . no
C12 C16 H16B 109.00 . . . no
C15 C16 H16B 109.00 . . . no
H16A C16 H16B 108.00 . . . no
C15 C16 H16A 109.00 . . . no



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
O1W Ni1 O1 C4 -152.73(18) . . . . no
O2W Ni1 O1 C4 -62.39(18) . . . . no
O3W Ni1 O1 C4 28.06(18) . . . . no
N1 Ni1 O1 C4 118.26(18) . . . . no
O1 Ni1 N1 C5 35.65(19) . . . . no
O1 Ni1 N1 C9 -142.37(18) . . . . no
O1W Ni1 N1 C5 -48.28(19) . . . . no
O1W Ni1 N1 C9 133.70(18) . . . . no
O3W Ni1 N1 C5 127.72(19) . . . . no
O3W Ni1 N1 C9 -50.30(18) . . . . no
N2 Ni1 N1 C5 -140.53(19) 2_656 . . . no
N2 Ni1 N1 C9 41.45(18) 2_656 . . . no
O1W Ni1 N2 C10 134.62(19) . . 2_656 2_656 no
O1W Ni1 N2 C14 -42.51(19) . . 2_656 2_656 no
O2W Ni1 N2 C10 44.85(19) . . 2_656 2_656 no
O2W Ni1 N2 C14 -132.27(18) . . 2_656 2_656 no
O3W Ni1 N2 C10 -45.70(19) . . 2_656 2_656 no
O3W Ni1 N2 C14 137.18(18) . . 2_656 2_656 no
N1 Ni1 N2 C10 -136.09(19) . . 2_656 2_656 no
N1 Ni1 N2 C14 46.79(19) . . 2_656 2_656 no
Ni1 O1 C4 O2 -27.6(3) . . . . no
Ni1 O1 C4 C1 154.65(14) . . . . no
Ni1 N1 C5 C6 180.0(2) . . . . no
C9 N1 C5 C6 -1.8(4) . . . . no
Ni1 N1 C9 C8 179.27(18) . . . . no
C5 N1 C9 C8 1.2(3) . . . . no
C14 N2 C10 C11 -1.8(4) . . . . no
Ni1 N2 C10 C11 -179.1(2) 2_656 . . . no
C10 N2 C14 C13 1.5(3) . . . . no
Ni1 N2 C14 C13 178.67(19) 2_656 . . . no
C4 C1 C2 C3 -30.7(3) . . . . no
C4 C1 C2 C2 94.96(19) . . . 2_555 no
C1 C1 C2 C3 -142.11(19) 2_555 . . . no
C1 C1 C2 C2 -16.49(14) 2_555 . . 2_555 no
C2 C1 C4 O1 -21.1(3) . . . . no
C2 C1 C4 O2 160.9(2) . . . . no
C1 C1 C4 O1 76.5(2) 2_555 . . . no
C1 C1 C4 O2 -101.4(2) 2_555 . . . no
C2 C1 C1 C2 16.27(14) . . 2_555 2_555 no
C2 C1 C1 C4 -99.86(17) . . 2_555 2_555 no
C4 C1 C1 C2 -99.86(17) . . 2_555 2_555 no
C4 C1 C1 C4 144.00(17) . . 2_555 2_555 no
C1 C2 C3 O3 125.9(2) . . . . no
C1 C2 C3 O4 -53.9(3) . . . . no
C2 C2 C3 O3 18.5(3) 2_555 . . . no
C2 C2 C3 O4 -161.32(18) 2_555 . . . no
C1 C2 C2 C1 16.69(14) . . 2_555 2_555 no
C1 C2 C2 C3 138.28(18) . . 2_555 2_555 no
C3 C2 C2 C1 138.28(18) . . 2_555 2_555 no
C3 C2 C2 C3 -100.1(2) . . 2_555 2_555 no
N1 C5 C6 C7 1.2(4) . . . . no
C5 C6 C7 C8 0.1(4) . . . . no
C5 C6 C7 C15 -177.7(3) . . . . no
C6 C7 C8 C9 -0.7(4) . . . . no
C15 C7 C8 C9 177.1(2) . . . . no
C6 C7 C15 C16 83.4(3) . . . . no
C8 C7 C15 C16 -94.3(3) . . . . no
C7 C8 C9 N1 0.0(4) . . . . no
N2 C10 C11 C12 0.4(4) . . . . no
C10 C11 C12 C13 1.4(4) . . . . no
C10 C11 C12 C16 -175.5(3) . . . . no
C11 C12 C13 C14 -1.6(4) . . . . no
C16 C12 C13 C14 175.1(3) . . . . no
C11 C12 C16 C15 81.3(3) . . . . no
C13 C12 C16 C15 -95.4(3) . . . . no
C12 C13 C14 N2 0.2(4) . . . . no
C7 C15 C16 C12 69.5(3) . . . . yes

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
O1W H1A O3 0.846(16) 2.035(17) 2.872(2) 170(2) .
O1W H1B O3 0.851(17) 2.97(2) 3.676(2) 141(2) 3_566
O2W H2A O3 0.856(17) 1.855(17) 2.707(2) 174(3) 3_566
O2W H2B O4 0.845(17) 2.011(17) 2.851(2) 172(3) .
O3W H3A O2 0.868(17) 1.837(18) 2.676(2) 162(3) .
O3W H3B O2 0.836(17) 1.958(17) 2.791(2) 173(3) 3_556
O4W H4A O4 0.850(19) 1.99(2) 2.826(4) 168(6) .

_refine_diff_density_max         0.306
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-3



loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?

_exptl_crystal_recrystallization_method 'Hydrothermal Synthesis'
