# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_g131206d
_database_code_depnum_ccdc_archive 'CCDC 1403254'
_audit_update_record             
;
2015-05-27 deposited with the CCDC.
2015-08-18 downloaded from the CCDC.
;
_audit_creation_date             2014-03-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C9 H5 O7 Zn, C7 H8 N2 O, 2(H2 O)'
_chemical_formula_sum            'C16 H17 N2 O10 Zn'
_chemical_formula_weight         462.69
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.1095(2)
_cell_length_b                   9.5924(4)
_cell_length_c                   13.2708(4)
_cell_angle_alpha                83.938(3)
_cell_angle_beta                 84.247(3)
_cell_angle_gamma                86.754(3)
_cell_volume                     894.46(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6706
_cell_measurement_temperature    278.18(10)
_cell_measurement_theta_max      29.9390
_cell_measurement_theta_min      3.6660
_exptl_absorpt_coefficient_mu    1.435
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             474
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10401
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.88
_diffrn_ambient_temperature      278.18(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0042921000
_diffrn_orient_matrix_UB_12      -0.0547509000
_diffrn_orient_matrix_UB_13      0.0403870000
_diffrn_orient_matrix_UB_21      -0.0995991000
_diffrn_orient_matrix_UB_22      -0.0001018000
_diffrn_orient_matrix_UB_23      -0.0008023000
_diffrn_orient_matrix_UB_31      0.0117551000
_diffrn_orient_matrix_UB_32      -0.0504350000
_diffrn_orient_matrix_UB_33      -0.0358253000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3847
_reflns_number_total             4090
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.688
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4090
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0268
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0285P)²+0.5056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0677
_refine_ls_wR_factor_ref         0.0690
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O10-H10A = O10-H10B
 0.85 with sigma of 0.01
3.a Rotating group:
 O8(H8A,H8B)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C12(H12), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Zn1 Zn 1.17649(3) 0.240557(19) 0.423641(14) 0.01726(7) Uani 1 d . . .
O1 O 0.98822(17) 0.26040(14) 0.53988(10) 0.0245(3) Uani 1 d . . .
O2 O 0.73188(17) 0.17095(14) 0.49365(9) 0.0238(3) Uani 1 d . . .
O3 O 0.7019(2) 0.50206(14) 0.54926(10) 0.0302(3) Uani 1 d . . .
O4 O 0.80519(19) 0.59571(13) 0.67732(10) 0.0250(3) Uani 1 d . . .
O5 O 0.86257(17) -0.07375(13) 0.64798(10) 0.0220(3) Uani 1 d . . .
O6 O 0.56115(18) -0.10873(13) 0.70056(11) 0.0286(3) Uani 1 d . . .
O7 O 0.0241(3) 0.25818(16) 1.00205(11) 0.0436(4) Uani 1 d . . .
O8 O 1.36510(18) 0.17200(15) 0.52003(10) 0.0279(3) Uani 1 d . . .
H8A H 1.3086 0.1328 0.5745 0.042 Uiso 1 d . . GR
H8B H 1.4249 0.2408 0.5344 0.042 Uiso 1 d . . GR
O9 O 0.2084(2) 1.02640(15) 0.69644(11) 0.0282(3) Uani 1 d . . .
H9A H 0.124(4) 0.985(3) 0.680(2) 0.044(8) Uiso 1 d . . .
H9B H 0.297(4) 0.978(3) 0.708(2) 0.043(8) Uiso 1 d . . .
O10 O 0.6387(4) 0.7183(3) 0.89515(18) 0.0852(7) Uani 1 d . . D
H10A H 0.644(7) 0.734(5) 0.8299(9) 0.128 Uiso 1 d . . DR
H10B H 0.754(3) 0.721(6) 0.910(4) 0.128 Uiso 1 d . . DR
N1 N 0.2635(2) 0.52172(18) 0.65448(13) 0.0250(3) Uani 1 d . . .
H1 H 0.293(4) 0.532(3) 0.591(2) 0.043(7) Uiso 1 d . . .
N2 N 0.1232(2) 0.23220(16) 0.83632(12) 0.0238(3) Uani 1 d . . .
H2 H 0.1366 0.1717 0.7924 0.029 Uiso 1 calc . . R
C1 C 0.7357(2) 0.22856(17) 0.66539(12) 0.0158(3) Uani 1 d . . .
C2 C 0.6835(2) 0.10793(17) 0.72844(13) 0.0178(3) Uani 1 d . . .
C3 C 0.6138(3) 0.11727(19) 0.82994(14) 0.0227(4) Uani 1 d . . .
H3 H 0.5744 0.0372 0.8705 0.027 Uiso 1 calc . . R
C4 C 0.6031(3) 0.24504(19) 0.87058(14) 0.0241(4) Uani 1 d . . .
H4 H 0.5622 0.2503 0.9389 0.029 Uiso 1 calc . . R
C5 C 0.6541(2) 0.36543(19) 0.80826(14) 0.0214(4) Uani 1 d . . .
H5 H 0.6473 0.4513 0.8354 0.026 Uiso 1 calc . . R
C6 C 0.7153(2) 0.35902(17) 0.70592(13) 0.0170(3) Uani 1 d . . .
C7 C 0.8212(2) 0.21844(17) 0.55679(13) 0.0159(3) Uani 1 d . . .
C8 C 0.7447(2) 0.49317(17) 0.63770(13) 0.0183(3) Uani 1 d . . .
C9 C 0.7008(2) -0.03461(17) 0.68976(13) 0.0185(3) Uani 1 d . . .
C10 C 0.2126(3) 0.39510(19) 0.69541(14) 0.0223(4) Uani 1 d . . .
H10 H 0.2087 0.3231 0.6541 0.027 Uiso 1 calc . . R
C11 C 0.1653(2) 0.37013(19) 0.79976(14) 0.0210(3) Uani 1 d . . .
C12 C 0.1693(3) 0.4815(2) 0.85851(15) 0.0306(4) Uani 1 d . . .
H12 H 0.1359 0.4691 0.9283 0.037 Uiso 1 calc . . R
C13 C 0.2235(3) 0.6110(2) 0.81211(16) 0.0352(5) Uani 1 d . . .
H13 H 0.2270 0.6857 0.8511 0.042 Uiso 1 calc . . R
C14 C 0.2719(3) 0.6303(2) 0.70917(16) 0.0311(4) Uani 1 d . . .
H14 H 0.3098 0.7169 0.6780 0.037 Uiso 1 calc . . R
C15 C 0.0633(3) 0.1830(2) 0.93363(15) 0.0269(4) Uani 1 d . . .
C16 C 0.0533(3) 0.0246(2) 0.94967(15) 0.0308(4) Uani 1 d . . .
H16A H -0.0087 -0.0070 0.8949 0.037 Uiso 1 calc . . R
H16B H 0.1807 -0.0176 0.9470 0.037 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 1.9562(12) . ?
Zn1 O4 1.9552(13) 2_766 ?
Zn1 O5 1.9913(12) 2_756 ?
Zn1 O8 1.9832(13) . ?
O1 C7 1.267(2) . ?
O2 C7 1.238(2) . ?
O3 C8 1.235(2) . ?
O4 Zn1 1.9552(13) 2_766 ?
O4 C8 1.277(2) . ?
O5 Zn1 1.9913(12) 2_756 ?
O5 C9 1.280(2) . ?
O6 C9 1.242(2) . ?
O7 C15 1.220(2) . ?
O8 H8A 0.8524 . ?
O8 H8B 0.8522 . ?
O9 H9A 0.80(3) . ?
O9 H9B 0.78(3) . ?
O10 H10A 0.861(10) . ?
O10 H10B 0.865(10) . ?
N1 H1 0.85(3) . ?
N1 C10 1.331(2) . ?
N1 C14 1.338(3) . ?
N2 H2 0.8600 . ?
N2 C11 1.398(2) . ?
N2 C15 1.362(2) . ?
C1 C2 1.400(2) . ?
C1 C6 1.408(2) . ?
C1 C7 1.518(2) . ?
C2 C3 1.398(2) . ?
C2 C9 1.505(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.391(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.391(2) . ?
C6 C8 1.505(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.391(2) . ?
C11 C12 1.391(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.371(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.516(3) . ?
C16 C16 1.512(4) 2_557 ?
C16 H16A 0.9700 . ?
C16 H16B 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 O5 112.26(5) . 2_756 ?
O1 Zn1 O8 88.94(6) . . ?
O4 Zn1 O1 115.24(6) 2_766 . ?
O4 Zn1 O5 108.24(5) 2_766 2_756 ?
O4 Zn1 O8 126.67(6) 2_766 . ?
O8 Zn1 O5 104.08(6) . 2_756 ?
C7 O1 Zn1 130.28(11) . . ?
C8 O4 Zn1 109.63(11) . 2_766 ?
C9 O5 Zn1 107.04(10) . 2_756 ?
Zn1 O8 H8A 109.5 . . ?
Zn1 O8 H8B 109.7 . . ?
H8A O8 H8B 109.3 . . ?
H9A O9 H9B 113(3) . . ?
H10A O10 H10B 105(5) . . ?
C10 N1 H1 117.3(18) . . ?
C10 N1 C14 123.15(17) . . ?
C14 N1 H1 119.5(18) . . ?
C11 N2 H2 116.3 . . ?
C15 N2 H2 116.3 . . ?
C15 N2 C11 127.31(16) . . ?
C2 C1 C6 118.77(15) . . ?
C2 C1 C7 120.71(14) . . ?
C6 C1 C7 120.46(15) . . ?
C1 C2 C9 121.45(15) . . ?
C3 C2 C1 120.38(15) . . ?
C3 C2 C9 118.17(15) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.44(17) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.43(16) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.83(16) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C8 120.49(15) . . ?
C5 C6 C1 120.00(16) . . ?
C5 C6 C8 119.35(15) . . ?
O1 C7 C1 113.59(14) . . ?
O2 C7 O1 125.24(15) . . ?
O2 C7 C1 121.16(14) . . ?
O3 C8 O4 123.17(16) . . ?
O3 C8 C6 119.76(15) . . ?
O4 C8 C6 116.98(15) . . ?
O5 C9 C2 117.26(14) . . ?
O6 C9 O5 123.28(15) . . ?
O6 C9 C2 119.46(15) . . ?
N1 C10 H10 119.9 . . ?
N1 C10 C11 120.26(17) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 N2 116.08(16) . . ?
C12 C11 N2 125.90(17) . . ?
C12 C11 C10 117.99(17) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.38(18) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.63(18) . . ?
C14 C13 H13 119.7 . . ?
N1 C14 C13 118.57(18) . . ?
N1 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
O7 C15 N2 123.57(18) . . ?
O7 C15 C16 122.87(18) . . ?
N2 C15 C16 113.55(16) . . ?
C15 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
C16 C16 C15 112.4(2) 2_557 . ?
C16 C16 H16A 109.1 2_557 . ?
C16 C16 H16B 109.1 2_557 . ?
H16A C16 H16B 107.9 . . ?

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
O9 H9A O5 0.80(3) 2.07(3) 2.845(2) 165(3) 1_465
O9 H9B O6 0.78(3) 2.00(3) 2.760(2) 162(3) 1_565
O10 H10A O6 0.861(10) 2.26(3) 3.000(3) 144(4) 1_565
O10 H10B O7 0.865(10) 2.09(2) 2.906(3) 158(5) 2_667
N1 H1 O3 0.85(3) 1.92(3) 2.723(2) 158(2) 2_666
N2 H2 O9 0.86 2.00 2.850(2) 171.2 1_545

_exptl_crystal_preparation       Luminescent
