# 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_bght217_0m
_audit_block_doi                 10.5517/cc13k8xv
_database_code_depnum_ccdc_archive 'CCDC 1029507'
_audit_update_record             
;
2014-10-16 deposited with the CCDC.
2015-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        MOF-1
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H12 N2 O5 Zn, C3 H3 N O2, C3 H7 N O'
_chemical_formula_sum            'C27 H22 N4 O8 Zn'
_chemical_formula_weight         595.88

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.361(5)
_cell_length_b                   15.532(5)
_cell_length_c                   16.269(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 94.661(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2861.3(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Needles
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1224.0
_exptl_absorpt_coefficient_mu    0.912
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_correction_T_min  0.769
_exptl_absorpt_correction_T_max  0.818
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            45877
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         26.23
_reflns_number_total             5765
_reflns_number_gt                4620
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker kappa apex ccd'
_computing_cell_refinement       'Bruker kappa apex ccd'
_computing_data_reduction        'Bruker saint'
_computing_structure_solution    shelxs-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  WinGX1.80.05

_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 > 2σ(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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1276P)²+13.4992P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5765
_refine_ls_number_parameters     417
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_ref         0.1913
_refine_ls_wR_factor_gt          0.1745
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_restrained_S_all      0.911
_refine_ls_shift/su_max          7.155
_refine_ls_shift/su_mean         0.422

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.02421(4) 0.12599(3) 0.03811(3) 0.01173(18) Uani 1 1 d . . .
O1 O 0.0302(3) 0.19925(18) 0.16157(18) 0.0245(7) Uani 1 1 d . . .
O2 O 0.0115(3) 0.26194(19) 0.04080(17) 0.0218(7) Uani 1 1 d . . .
O3 O -0.0505(4) 0.5716(2) 0.09436(19) 0.0392(10) Uani 1 1 d . . .
N1 N -0.1640(3) 0.1184(2) 0.0407(2) 0.0194(7) Uani 1 1 d . . .
N2 N 0.2128(3) 0.1290(2) 0.0390(2) 0.0202(7) Uani 1 1 d . . .
C12 C 0.0010(4) 0.3518(3) 0.1582(3) 0.0189(8) Uani 1 1 d . . .
C14 C -0.0160(3) 0.4360(2) 0.2803(2) 0.0154(8) Uani 1 1 d . . .
C8 C 0.4592(4) 0.1249(3) 0.0399(3) 0.0250(10) Uani 1 1 d . . .
C11 C 0.0160(4) 0.2653(3) 0.1180(3) 0.0198(9) Uani 1 1 d . . .
C3 C -0.4103(4) 0.1221(3) 0.0402(3) 0.0265(10) Uani 1 1 d . . .
C13 C 0.0031(4) 0.3574(3) 0.2433(3) 0.0195(9) Uani 1 1 d . . .
C17 C -0.0181(4) 0.4240(3) 0.1097(3) 0.0236(9) Uani 1 1 d . . .
C16 C -0.0360(5) 0.5036(3) 0.1470(3) 0.0255(10) Uani 1 1 d . . .
C15 C -0.0374(4) 0.5097(3) 0.2325(3) 0.0204(9) Uani 1 1 d . . .
C4 C -0.3420(4) 0.0791(4) 0.0994(3) 0.0373(13) Uani 1 1 d . . .
C7 C 0.3893(4) 0.1465(4) -0.0295(3) 0.0338(12) Uani 1 1 d . . .
C5 C -0.2207(4) 0.0786(4) 0.0977(3) 0.0353(12) Uani 1 1 d . . .
C6 C 0.2676(4) 0.1474(3) -0.0278(3) 0.0308(11) Uani 1 1 d . . .
C2 C -0.3513(5) 0.1670(6) -0.0179(4) 0.069(2) Uani 1 1 d . . .
C9 C 0.4026(5) 0.1106(6) 0.1105(4) 0.055(2) Uani 1 1 d . . .
C10 C 0.2804(4) 0.1137(5) 0.1074(3) 0.0468(16) Uani 1 1 d . . .
C1 C -0.2295(5) 0.1648(5) -0.0147(4) 0.0562(19) Uani 1 1 d . . .
C18 C -0.0759(7) 0.6537(3) 0.1290(3) 0.0530(19) Uani 1 1 d . . .
C19 C -0.1992(8) 0.6589(4) 0.1507(4) 0.061(2) Uani 1 1 d . . .
O4 O 0.0126(3) 0.12405(17) -0.08692(17) 0.0162(6) Uani 1 1 d . . .
O5 O 0.0474(3) 0.01194(18) 0.09754(17) 0.0188(6) Uani 1 1 d . . .
C20 C 0.0170(3) -0.0578(2) 0.1280(2) 0.0139(8) Uani 1 1 d . . .
C21 C -0.2996(11) 0.6665(8) 0.1669(6) 0.101(4) Uani 1 1 d D . .
C1S C 0.2998(10) 0.3705(8) 0.0712(8) 0.112(4) Uani 1 1 d . . .
H1S1 H 0.3142 0.3107 0.0833 0.167 Uiso 1 1 calc R . .
H1S2 H 0.3527 0.3898 0.0320 0.167 Uiso 1 1 calc R . .
H1S3 H 0.2197 0.3779 0.0487 0.167 Uiso 1 1 calc R . .
N1S N 0.3172(11) 0.4153(13) 0.1386(8) 0.173(7) Uani 1 1 d D . .
O1S O -0.5546(11) 0.7098(14) 0.1984(8) 0.240(8) Uani 1 1 d . . .
N2S N -0.366(2) 0.3723(16) 0.1936(17) 0.326(17) Uani 1 1 d D . .
C4S C -0.328(3) 0.2926(18) 0.229(2) 0.70(4) Uani 1 1 d D . .
H4S H -0.3991 0.2632 0.2266 0.836 Uiso 1 1 calc R . .
C3S C -0.360(3) 0.384(4) 0.1050(17) 0.55(4) Uani 1 1 d D . .
C2S C 0.331(2) 0.392(3) 0.2241(13) 0.50(4) Uani 1 1 d D . .
H2S1 H 0.3445 0.4427 0.2571 0.752 Uiso 1 1 calc R . .
H2S2 H 0.3965 0.3534 0.2336 0.752 Uiso 1 1 calc R . .
H2S3 H 0.2601 0.3640 0.2390 0.752 Uiso 1 1 calc R . .
O2S O -0.251(2) 0.2278(15) 0.2666(15) 0.51(2) Uani 1 1 d D . .
O3S O 0.293(3) 0.527(3) 0.053(2) 0.65(3) Uani 1 1 d . . .
C6S C -0.355(2) 0.4192(19) 0.2615(19) 0.313(16) Uani 1 1 d D . .
C7S C 0.307(2) 0.4999(19) 0.140(2) 0.359(13) Uani 1 1 d . . .
H7S H 0.3080 0.5349 0.1868 0.431 Uiso 1 1 calc R . .
H1W H -0.566(4) 0.764(3) 0.238(3) 0.000(9) Uiso 1 1 d . . .
H2 H -0.014(4) 0.422(3) 0.050(3) 0.016(11) Uiso 1 1 d . . .
H4 H 0.018(4) 0.314(3) 0.277(3) 0.023(13) Uiso 1 1 d . . .
H3 H -0.054(4) 0.565(3) 0.254(3) 0.017(11) Uiso 1 1 d . . .
H2W H -0.600(7) 0.675(5) 0.142(5) 0.06(2) Uiso 1 1 d . . .
H7 H -0.379(7) 0.026(5) 0.134(5) 0.09(2) Uiso 1 1 d . . .
H10 H 0.223(5) 0.164(4) -0.072(4) 0.035(14) Uiso 1 1 d . . .
H13 H 0.436(8) 0.099(6) 0.166(6) 0.10(3) Uiso 1 1 d . . .
H12 H 0.232(6) 0.117(4) 0.157(4) 0.06(2) Uiso 1 1 d . . .
H6 H -0.172(7) 0.041(5) 0.140(5) 0.07(2) Uiso 1 1 d . . .
H11 H 0.418(7) 0.153(5) -0.077(5) 0.05(2) Uiso 1 1 d . . .
H8 H -0.394(7) 0.204(5) -0.053(5) 0.07(2) Uiso 1 1 d . . .
H9 H -0.184(7) 0.211(5) -0.050(5) 0.08(3) Uiso 1 1 d . . .
H1 H -0.371(6) 0.681(8) 0.198(6) 0.16(4) Uiso 1 1 d D . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 O5 2.025(3) . ?
Zn1 O4 2.028(3) . ?
Zn1 O2 2.117(3) . ?
Zn1 N2 2.142(4) . ?
Zn1 N1 2.145(4) . ?
Zn1 O1 2.305(3) . ?
Zn1 C11 2.530(4) . ?
O1 C11 1.250(5) . ?
O2 C11 1.254(5) . ?
O3 C16 1.361(5) . ?
O3 C18 1.434(6) . ?
N1 C5 1.325(6) . ?
N1 C1 1.333(7) . ?
N2 C10 1.321(7) . ?
N2 C6 1.327(6) . ?
C12 C17 1.378(6) . ?
C12 C13 1.385(6) . ?
C12 C11 1.509(5) . ?
C14 C13 1.386(5) . ?
C14 C15 1.395(6) . ?
C14 C20 1.495(5) 2 ?
C8 C9 1.378(7) . ?
C8 C7 1.368(7) . ?
C8 C3 1.483(6) 1_655 ?
C3 C4 1.361(7) . ?
C3 C2 1.391(8) . ?
C3 C8 1.483(6) 1_455 ?
C17 C16 1.400(6) . ?
C16 C15 1.396(6) . ?
C4 C5 1.380(7) . ?
C7 C6 1.386(7) . ?
C2 C1 1.381(8) . ?
C9 C10 1.387(7) . ?
C18 C19 1.474(11) . ?
C19 C21 1.197(13) . ?
O4 C20 1.258(5) 3 ?
O5 C20 1.252(5) . ?
C20 O4 1.258(5) 3 ?
C20 C14 1.495(5) 2_545 ?
C1S N1S 1.299(13) . ?
N1S C7S 1.32(3) . ?
N1S C2S 1.434(10) . ?
N2S C3S 1.46(3) . ?
N2S C6S 1.32(3) . ?
N2S C4S 1.420(10) . ?
C4S O2S 1.431(11) . ?
C3S C6S 2.602(11) . ?
O3S C7S 1.49(3) . ?

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
O5 Zn1 O4 117.47(11) . . ?
O5 Zn1 O2 150.34(11) . . ?
O4 Zn1 O2 92.10(11) . . ?
O5 Zn1 N2 85.65(13) . . ?
O4 Zn1 N2 89.48(13) . . ?
O2 Zn1 N2 92.75(13) . . ?
O5 Zn1 N1 91.94(13) . . ?
O4 Zn1 N1 92.00(13) . . ?
O2 Zn1 N1 89.13(12) . . ?
N2 Zn1 N1 177.56(13) . . ?
O5 Zn1 O1 91.28(11) . . ?
O4 Zn1 O1 151.22(11) . . ?
O2 Zn1 O1 59.12(10) . . ?
N2 Zn1 O1 91.39(13) . . ?
N1 Zn1 O1 88.24(13) . . ?
O5 Zn1 C11 120.78(13) . . ?
O4 Zn1 C11 121.72(12) . . ?
O2 Zn1 C11 29.64(13) . . ?
N2 Zn1 C11 93.23(14) . . ?
N1 Zn1 C11 87.64(13) . . ?
O1 Zn1 C11 29.51(12) . . ?
C11 O1 Zn1 85.3(2) . . ?
C11 O2 Zn1 93.7(3) . . ?
C16 O3 C18 117.4(3) . . ?
C5 N1 C1 116.7(4) . . ?
C5 N1 Zn1 125.6(3) . . ?
C1 N1 Zn1 117.4(3) . . ?
C10 N2 C6 116.7(4) . . ?
C10 N2 Zn1 121.0(3) . . ?
C6 N2 Zn1 122.3(3) . . ?
C17 C12 C13 120.7(4) . . ?
C17 C12 C11 119.6(4) . . ?
C13 C12 C11 119.7(4) . . ?
C13 C14 C15 120.5(4) . . ?
C13 C14 C20 120.3(4) . 2 ?
C15 C14 C20 119.2(3) . 2 ?
C9 C8 C7 116.6(4) . . ?
C9 C8 C3 121.8(5) . 1_655 ?
C7 C8 C3 121.5(4) . 1_655 ?
O2 C11 O1 121.8(4) . . ?
O2 C11 C12 118.3(4) . . ?
O1 C11 C12 119.9(4) . . ?
O2 C11 Zn1 56.6(2) . . ?
O1 C11 Zn1 65.2(2) . . ?
C12 C11 Zn1 173.6(3) . . ?
C4 C3 C2 116.7(4) . . ?
C4 C3 C8 121.9(4) . 1_455 ?
C2 C3 C8 121.3(5) . 1_455 ?
C14 C13 C12 119.9(4) . . ?
C12 C17 C16 119.5(4) . . ?
O3 C16 C15 124.3(4) . . ?
O3 C16 C17 115.3(4) . . ?
C15 C16 C17 120.4(4) . . ?
C16 C15 C14 119.0(4) . . ?
C3 C4 C5 120.1(4) . . ?
C8 C7 C6 119.9(5) . . ?
N1 C5 C4 123.7(4) . . ?
N2 C6 C7 123.3(5) . . ?
C3 C2 C1 119.9(5) . . ?
C8 C9 C10 119.9(5) . . ?
N2 C10 C9 123.2(5) . . ?
N1 C1 C2 122.8(5) . . ?
O3 C18 C19 111.6(6) . . ?
C21 C19 C18 177.2(8) . . ?
C20 O4 Zn1 122.6(2) 3 . ?
C20 O5 Zn1 156.5(3) . . ?
O4 C20 O5 124.6(3) 3 . ?
O4 C20 C14 117.0(3) 3 2_545 ?
O5 C20 C14 118.4(3) . 2_545 ?
C1S N1S C7S 123(2) . . ?
C1S N1S C2S 133(3) . . ?
C7S N1S C2S 103(3) . . ?
C3S N2S C6S 139(3) . . ?
C3S N2S C4S 118(3) . . ?
C6S N2S C4S 98(2) . . ?
N2S C4S O2S 160(3) . . ?
N2S C3S C6S 19.7(13) . . ?
N2S C6S C3S 21.8(17) . . ?
O3S C7S N1S 106(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.23
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.389
_refine_diff_density_min         -0.770
_refine_diff_density_rms         0.127
####################################################################### 
# 
# 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_MOF-2
_audit_block_doi                 10.5517/cc13k8yw
_database_code_depnum_ccdc_archive 'CCDC 1029508'
_audit_update_record             
;
2014-10-16 deposited with the CCDC.
2015-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        MOF-2
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H14 N2 O5 Zn'
_chemical_formula_sum            'C23 H14 N2 O5 Zn'
_chemical_formula_weight         463.75

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_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                   29.971(8)
_cell_length_b                   16.271(4)
_cell_length_c                   15.804(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.749(7)
_cell_angle_gamma                90.00
_cell_volume                     6942(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Needles
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.887
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1888.0
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_correction_T_min  0.818
_exptl_absorpt_correction_T_max  0.858
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            76513
_diffrn_reflns_av_R_equivalents  0.0859
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         26.37
_reflns_number_total             7085
_reflns_number_gt                4780
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker kappa apex ccd'
_computing_cell_refinement       'Bruker kappa apex ccd'
_computing_data_reduction        'Bruker saint'
_computing_structure_solution    shelxs-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  WinGX1.80.05

_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 > 2σ(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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7085
_refine_ls_number_parameters     280
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.1319
_refine_ls_R_factor_gt           0.1051
_refine_ls_wR_factor_ref         0.3192
_refine_ls_wR_factor_gt          0.3014
_refine_ls_goodness_of_fit_ref   1.215
_refine_ls_restrained_S_all      1.222
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.24686(2) 0.21143(3) 0.37151(3) 0.0405(3) Uani 1 1 d . . .
O4 O 0.24791(13) 0.3364(2) 0.3746(2) 0.0486(9) Uani 1 1 d . . .
O1 O 0.25047(16) 0.20610(19) 0.2394(3) 0.0530(10) Uani 1 1 d . . .
N2 N 0.3262(2) 0.2079(3) 0.4458(4) 0.0600(13) Uani 1 1 d . . .
N1 N 0.1672(2) 0.2139(3) 0.2957(4) 0.0607(13) Uani 1 1 d . . .
C13 C 0.2539(2) 0.3747(3) 0.4477(3) 0.0441(12) Uani 1 1 d . . .
C10 C 0.2468(2) 0.0885(3) 0.1476(3) 0.0500(14) Uani 1 1 d . . .
C11 C 0.2497(2) 0.1307(3) 0.2350(4) 0.0491(13) Uani 1 1 d . . .
C3 C 0.0635(4) 0.2166(8) 0.1868(11) 0.136(5) Uani 1 1 d . . .
C2 C 0.0980(5) 0.2856(9) 0.1812(14) 0.213(10) Uani 1 1 d D . .
H2 H 0.0854 0.3305 0.1414 0.256 Uiso 1 1 calc R . .
C6 C 0.3512(4) 0.1570(8) 0.5125(12) 0.173(6) Uani 1 1 d . . .
H6 H 0.3337 0.1184 0.5297 0.208 Uiso 1 1 calc R . .
C4 C 0.0870(4) 0.1532(8) 0.2365(10) 0.149(5) Uani 1 1 d . . .
H4 H 0.0692 0.1062 0.2359 0.178 Uiso 1 1 calc R . .
C1 C 0.1464(4) 0.2778(7) 0.2360(12) 0.167(7) Uani 1 1 d . . .
H1 H 0.1674 0.3187 0.2331 0.200 Uiso 1 1 calc R . .
C5 C 0.1371(4) 0.1541(6) 0.2896(8) 0.117(3) Uani 1 1 d . . .
H5 H 0.1511 0.1073 0.3249 0.141 Uiso 1 1 calc R . .
C14 C 0.3526(4) 0.2647(9) 0.4256(10) 0.149(5) Uani 1 1 d . . .
H14 H 0.3361 0.3043 0.3804 0.179 Uiso 1 1 calc R . .
C8 C 0.4306(4) 0.2102(7) 0.5409(10) 0.123(4) Uani 1 1 d . . .
C9 C 0.4038(5) 0.2655(12) 0.4705(15) 0.207(9) Uani 1 1 d . . .
H9 H 0.4209 0.3045 0.4527 0.249 Uiso 1 1 calc R . .
C7 C 0.4043(6) 0.1565(10) 0.5616(16) 0.240(11) Uani 1 1 d . . .
H7 H 0.4202 0.1178 0.6085 0.288 Uiso 1 1 calc R . .
O3 O 0.24794(17) 0.0862(2) 0.2998(3) 0.0627(11) Uani 1 1 d . . .
C15 C 0.2559(2) 0.4661(3) 0.4386(3) 0.0438(12) Uani 1 1 d . . .
C17 C 0.25269(17) 0.5049(3) 0.3592(3) 0.0425(12) Uani 1 1 d . . .
H17 H 0.2501 0.4732 0.3082 0.051 Uiso 1 1 calc R . .
C18 C 0.2598(3) 0.5146(3) 0.5165(4) 0.076(2) Uani 1 1 d . . .
H18 H 0.2618 0.4899 0.5711 0.091 Uiso 1 1 calc R . .
C19 C 0.2605(4) 0.5997(4) 0.5092(5) 0.098(3) Uani 1 1 d . . .
C20 C 0.2429(4) 0.1382(3) 0.0729(5) 0.089(3) Uani 1 1 d . . .
H20 H 0.2424 0.1952 0.0772 0.107 Uiso 1 1 calc R . .
O2 O 0.2612(2) 0.3457(2) 0.5237(3) 0.0752(14) Uani 1 1 d . . .
O5 O 0.2663(3) 0.6534(2) 0.5829(4) 0.140(3) Uani 1 1 d . . .
C24 C 0.2811(6) 0.6190(6) 0.6757(6) 0.153(6) Uani 1 1 d D . .
H24A H 0.2620 0.5697 0.6711 0.184 Uiso 1 1 calc R . .
H24B H 0.2742 0.6582 0.7148 0.184 Uiso 1 1 calc R . .
C25 C 0.3397(9) 0.5967(8) 0.7241(12) 0.180(8) Uani 1 1 d DU . .
C26 C 0.3873(14) 0.5783(18) 0.7732(17) 0.336(19) Uani 1 1 d U . .
H26 H 0.4206 0.5654 0.8075 0.403 Uiso 1 1 calc R . .
C2B C 0.4673(4) 0.2897(5) 0.6357(7) 0.037(2) Uiso 0.48 1 d P . .
C1B C 0.0236(4) 0.2830(6) 0.1114(9) 0.054(3) Uiso 0.52 1 d PD . .
C1A C 0.0056(7) 0.2172(10) 0.1240(14) 0.092(5) Uiso 0.48 1 d P . .
C2A C 0.4832(7) 0.2049(9) 0.5910(13) 0.092(5) Uiso 0.52 1 d P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O2 2.004(4) 7_556 ?
Zn1 O4 2.033(4) . ?
Zn1 N2 2.146(6) . ?
Zn1 O1 2.139(4) . ?
Zn1 N1 2.157(5) . ?
Zn1 O3 2.339(4) . ?
Zn1 C11 2.558(5) . ?
O4 C13 1.256(5) . ?
O1 C11 1.229(6) . ?
N2 C6 1.294(13) . ?
N2 C14 1.342(12) . ?
N1 C5 1.303(10) . ?
N1 C1 1.359(12) . ?
C13 O2 1.218(6) . ?
C13 C15 1.498(6) . ?
C10 C17 1.365(7) 4_545 ?
C10 C20 1.393(7) . ?
C10 C11 1.512(7) . ?
C11 O3 1.273(6) . ?
C3 C4 1.302(15) . ?
C3 C2 1.556(19) . ?
C3 C1A 1.58(2) . ?
C3 C1B 1.667(17) . ?
C2 C1 1.335(16) . ?
C2 C1B 2.013(17) . ?
C6 C7 1.438(17) . ?
C4 C5 1.365(14) . ?
C14 C9 1.385(16) . ?
C8 C7 1.31(2) . ?
C8 C9 1.385(19) . ?
C8 C2A 1.43(2) . ?
C8 C2B 1.922(15) . ?
C15 C17 1.370(6) . ?
C15 C18 1.423(7) . ?
C17 C10 1.365(7) 4 ?
C18 C19 1.391(8) . ?
C19 O5 1.406(7) . ?
C19 C20 1.404(8) 4 ?
C20 C19 1.404(8) 4_545 ?
O2 Zn1 2.004(4) 7_556 ?
O5 C24 1.448(10) . ?
C24 C25 1.62(2) . ?
C25 C26 1.33(3) . ?
C2B C1A 1.24(2) 8_556 ?
C2B C2A 1.710(19) . ?
C1B C2A 1.13(2) 8_455 ?
C1B C1A 1.254(19) . ?
C1A C2B 1.24(2) 8_455 ?
C1A C2A 1.42(2) 8_455 ?
C2A C1B 1.13(2) 8_556 ?
C2A C1A 1.42(2) 8_556 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Zn1 O4 116.73(13) 7_556 . ?
O2 Zn1 N2 92.2(2) 7_556 . ?
O4 Zn1 N2 90.66(16) . . ?
O2 Zn1 O1 149.74(13) 7_556 . ?
O4 Zn1 O1 93.29(12) . . ?
N2 Zn1 O1 91.11(19) . . ?
O2 Zn1 N1 88.1(2) 7_556 . ?
O4 Zn1 N1 89.78(16) . . ?
N2 Zn1 N1 179.32(19) . . ?
O1 Zn1 N1 88.35(19) . . ?
O2 Zn1 O3 91.66(14) 7_556 . ?
O4 Zn1 O3 151.57(12) . . ?
N2 Zn1 O3 89.82(17) . . ?
O1 Zn1 O3 58.28(12) . . ?
N1 Zn1 O3 89.55(18) . . ?
O2 Zn1 C11 121.27(17) 7_556 . ?
O4 Zn1 C11 121.88(15) . . ?
N2 Zn1 C11 90.74(19) . . ?
O1 Zn1 C11 28.58(15) . . ?
N1 Zn1 C11 88.6(2) . . ?
O3 Zn1 C11 29.69(15) . . ?
C13 O4 Zn1 120.9(3) . . ?
C11 O1 Zn1 95.0(3) . . ?
C6 N2 C14 116.2(9) . . ?
C6 N2 Zn1 125.1(7) . . ?
C14 N2 Zn1 118.6(6) . . ?
C5 N1 C1 115.2(8) . . ?
C5 N1 Zn1 126.3(6) . . ?
C1 N1 Zn1 117.6(5) . . ?
O2 C13 O4 127.3(4) . . ?
O2 C13 C15 118.9(4) . . ?
O4 C13 C15 113.6(4) . . ?
C17 C10 C20 120.8(4) 4_545 . ?
C17 C10 C11 121.7(4) 4_545 . ?
C20 C10 C11 117.5(4) . . ?
O1 C11 O3 121.9(5) . . ?
O1 C11 C10 119.8(5) . . ?
O3 C11 C10 118.1(4) . . ?
O1 C11 Zn1 56.4(3) . . ?
O3 C11 Zn1 65.5(3) . . ?
C10 C11 Zn1 173.9(4) . . ?
C4 C3 C2 114.0(10) . . ?
C4 C3 C1A 122.9(12) . . ?
C2 C3 C1A 122.4(12) . . ?
C4 C3 C1B 167.6(11) . . ?
C2 C3 C1B 77.2(9) . . ?
C1A C3 C1B 45.3(7) . . ?
C1 C2 C3 117.2(11) . . ?
C1 C2 C1B 170.8(14) . . ?
C3 C2 C1B 53.9(7) . . ?
N2 C6 C7 123.8(13) . . ?
C3 C4 C5 121.6(11) . . ?
N1 C1 C2 124.4(10) . . ?
N1 C5 C4 126.6(9) . . ?
N2 C14 C9 121.5(11) . . ?
C7 C8 C9 115.7(11) . . ?
C7 C8 C2A 117.5(13) . . ?
C9 C8 C2A 126.8(14) . . ?
C7 C8 C2B 117.2(15) . . ?
C9 C8 C2B 97.1(11) . . ?
C2A C8 C2B 59.2(8) . . ?
C8 C9 C14 122.1(13) . . ?
C8 C7 C6 120.5(14) . . ?
C11 O3 Zn1 84.8(3) . . ?
C17 C15 C18 119.0(4) . . ?
C17 C15 C13 123.7(4) . . ?
C18 C15 C13 117.3(4) . . ?
C10 C17 C15 122.1(4) 4 . ?
C19 C18 C15 118.6(5) . . ?
O5 C19 C18 123.4(6) . . ?
O5 C19 C20 114.9(5) . 4 ?
C18 C19 C20 121.6(5) . 4 ?
C10 C20 C19 118.0(5) . 4_545 ?
C13 O2 Zn1 163.8(5) . 7_556 ?
C19 O5 C24 118.2(5) . . ?
O5 C24 C25 110.9(11) . . ?
C26 C25 C24 173(2) . . ?
C1A C2B C2A 54.8(10) 8_556 . ?
C1A C2B C8 94.3(11) 8_556 . ?
C2A C2B C8 45.8(7) . . ?
C2A C1B C1A 73.1(12) 8_455 . ?
C2A C1B C3 131.7(14) 8_455 . ?
C1A C1B C3 63.7(11) . . ?
C2A C1B C2 161.7(14) 8_455 . ?
C1A C1B C2 112.5(13) . . ?
C3 C1B C2 48.9(6) . . ?
C1B C1A C2B 126.2(16) . 8_455 ?
C1B C1A C2A 49.3(10) . 8_455 ?
C2B C1A C2A 79.5(15) 8_455 8_455 ?
C1B C1A C3 70.9(12) . . ?
C2B C1A C3 137.5(17) 8_455 . ?
C2A C1A C3 116.7(15) 8_455 . ?
C1B C2A C1A 57.6(12) 8_556 8_556 ?
C1B C2A C8 160.0(17) 8_556 . ?
C1A C2A C8 112.4(15) 8_556 . ?
C1B C2A C2B 101.5(12) 8_556 . ?
C1A C2A C2B 45.7(10) 8_556 . ?
C8 C2A C2B 75.0(10) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         2.514
_refine_diff_density_min         -0.918
_refine_diff_density_rms         0.140
