# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2010


data_global
_journal_name_full               'Dalton Trans.'

_journal_coden_Cambridge         0222

_publ_contact_author_name        'Aakeroy, C.'
_publ_contact_author_email       aakeroy@ksu.edu

_publ_section_title              
;
The role of metal ions and counterions in the switching behavior
of a carboxylic acid functionalized spiropyran
;
loop_
_publ_author_name
C.Aakeroy
S.Giordani

# Attachment '- eh0902m.cif'

data_eh0902m
_database_code_depnum_ccdc_archive 'CCDC 771869'
#TrackingRef '- eh0902m.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
EH-02-77-01 methoxy nitro propiony spiropyran Zn(ClO4)2
;
_chemical_name_common            
'EH-02-77-01 methoxy nitro propiony spiropyran Zn(ClO4)2'
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C23 H23 N2 O6) Zn Cl
;
_chemical_formula_sum            'C23 H23 Cl N2 O6 Zn'
_chemical_formula_weight         524.25

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'
Cl Cl 0.1484 0.1585 '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   P2(1)/c

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                   9.000(10)
_cell_length_b                   7.729(9)
_cell_length_c                   37.55(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.774(8)
_cell_angle_gamma                90.00
_cell_volume                     2603(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4330
_cell_measurement_theta_min      8.01
_cell_measurement_theta_max      24.34

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    1.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8457
_exptl_absorpt_correction_T_max  0.9378
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            61286
_diffrn_reflns_av_R_equivalents  0.3846
_diffrn_reflns_av_sigmaI/netI    0.2150
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_theta_min         7.77
_diffrn_reflns_theta_max         28.92
_reflns_number_total             6509
_reflns_number_gt                2734
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6509
_refine_ls_number_parameters     281
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.3601
_refine_ls_R_factor_gt           0.2237
_refine_ls_wR_factor_ref         0.4679
_refine_ls_wR_factor_gt          0.4372
_refine_ls_goodness_of_fit_ref   1.972
_refine_ls_restrained_S_all      1.971
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.5885(3) 0.2584(2) 0.30101(3) 0.0664(8) Uani 1 1 d . . .
Cl1 Cl 0.8329(6) 0.3397(5) 0.31313(10) 0.0863(17) Uani 1 1 d . . .
N11 N 0.2559(17) 0.7408(19) 0.3813(3) 0.078(4) Uani 1 1 d . . .
C12 C 0.287(3) 0.605(2) 0.4066(4) 0.100(8) Uani 1 1 d D . .
C13 C 0.2044(15) 0.6514(14) 0.4403(3) 0.075(5) Uani 1 1 d D . .
C14 C 0.1211(14) 0.8153(13) 0.4301(2) 0.065(5) Uani 1 1 d GD . .
C15 C 0.0267(13) 0.9184(14) 0.4485(2) 0.086(6) Uani 1 1 d G . .
H15 H 0.0041 0.8869 0.4719 0.103 Uiso 1 1 calc R . .
C16 C -0.0347(12) 1.0674(13) 0.4326(3) 0.104(8) Uani 1 1 d G . .
H16 H -0.0993 1.1378 0.4452 0.124 Uiso 1 1 calc R . .
C17 C -0.0017(15) 1.1133(13) 0.3984(3) 0.091(7) Uani 1 1 d G . .
H17 H -0.0437 1.2152 0.3876 0.109 Uiso 1 1 calc R . .
C18 C 0.0927(17) 1.0103(16) 0.3800(2) 0.103(8) Uani 1 1 d G . .
H18 H 0.1153 1.0417 0.3566 0.124 Uiso 1 1 calc R . .
C19 C 0.1542(15) 0.8612(15) 0.3959(2) 0.089(7) Uani 1 1 d G . .
C20 C 0.3164(19) 0.668(3) 0.4736(3) 0.102(7) Uani 1 1 d D . .
H20A H 0.3696 0.5587 0.4778 0.152 Uiso 1 1 calc R . .
H20B H 0.2627 0.6970 0.4945 0.152 Uiso 1 1 calc R . .
H20C H 0.3881 0.7604 0.4696 0.152 Uiso 1 1 calc R . .
C21 C 0.0994(16) 0.502(2) 0.4487(5) 0.084(6) Uani 1 1 d D . .
H21A H 0.0266 0.4829 0.4282 0.127 Uiso 1 1 calc R . .
H21B H 0.0470 0.5317 0.4698 0.127 Uiso 1 1 calc R . .
H21C H 0.1578 0.3963 0.4536 0.127 Uiso 1 1 calc R . .
C22 C 0.299(2) 0.765(2) 0.3439(3) 0.101(7) Uani 1 1 d DU . .
H22A H 0.4021 0.7207 0.3427 0.121 Uiso 1 1 calc R . .
H22B H 0.3005 0.8900 0.3386 0.121 Uiso 1 1 calc R . .
C23 C 0.1979(18) 0.675(3) 0.3145(3) 0.082(5) Uani 1 1 d DU . .
H23A H 0.0976 0.7279 0.3127 0.098 Uiso 1 1 calc R . .
H23B H 0.1874 0.5503 0.3202 0.098 Uiso 1 1 calc R . .
C24 C 0.270(2) 0.695(3) 0.2787(4) 0.103(6) Uani 1 1 d DU . .
H24A H 0.1910 0.6752 0.2593 0.124 Uiso 1 1 calc R . .
H24B H 0.3009 0.8178 0.2770 0.124 Uiso 1 1 calc R . .
C25 C 0.4051(16) 0.5832(18) 0.2706(3) 0.057(4) Uani 1 1 d DU . .
O25 O 0.4503(15) 0.4637(13) 0.2945(2) 0.080(4) Uani 1 1 d . . .
O26 O 0.4630(14) 0.5966(12) 0.2401(2) 0.070(3) Uani 1 1 d . . .
C27 C 0.377(2) 0.4514(17) 0.3963(3) 0.085(6) Uani 1 1 d D . .
H27 H 0.4169 0.4480 0.3737 0.103 Uiso 1 1 calc R . .
C28 C 0.4047(13) 0.2994(12) 0.4227(3) 0.039(3) Uiso 1 1 d D . .
H28 H 0.3633 0.2959 0.4451 0.047 Uiso 1 1 calc R . .
C31 C 0.5456(17) 0.1210(15) 0.3753(3) 0.044(3) Uani 1 1 d . . .
C32 C 0.6294(17) -0.0397(18) 0.3686(3) 0.051(4) Uani 1 1 d . . .
C33 C 0.6748(17) -0.1497(19) 0.3983(3) 0.064(4) Uani 1 1 d . . .
H33 H 0.7318 -0.2509 0.3949 0.076 Uiso 1 1 calc R . .
C34 C 0.6331(16) -0.105(2) 0.4337(4) 0.070(5) Uani 1 1 d . . .
C35 C 0.5494(19) 0.041(2) 0.4393(4) 0.066(5) Uani 1 1 d . . .
H35 H 0.5227 0.0659 0.4627 0.080 Uiso 1 1 calc R . .
C36 C 0.5015(17) 0.1578(16) 0.4103(3) 0.058(4) Uani 1 1 d D . .
O31 O 0.4925(13) 0.2135(11) 0.3474(2) 0.063(3) Uani 1 1 d . . .
O32 O 0.6584(12) -0.0652(11) 0.3336(2) 0.056(3) Uani 1 1 d . . .
N34 N 0.685(2) -0.221(2) 0.4634(4) 0.097(6) Uani 1 1 d . . .
O34 O 0.7389(17) -0.375(2) 0.4553(3) 0.109(5) Uani 1 1 d . . .
O35 O 0.6725(19) -0.178(2) 0.4943(3) 0.127(7) Uani 1 1 d . . .
C37 C 0.749(2) -0.2132(17) 0.3242(4) 0.067(5) Uani 1 1 d . . .
H37A H 0.7543 -0.2162 0.2983 0.101 Uiso 1 1 calc R . .
H37B H 0.7026 -0.3203 0.3320 0.101 Uiso 1 1 calc R . .
H37C H 0.8491 -0.2024 0.3362 0.101 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Zn1 0.143(2) 0.0349(8) 0.0239(7) -0.0024(6) 0.0202(8) -0.0001(11)
Cl1 0.156(5) 0.048(2) 0.056(2) -0.0045(17) 0.014(3) 0.003(3)
N11 0.105(11) 0.088(10) 0.043(6) 0.020(7) 0.019(7) 0.046(9)
C12 0.18(2) 0.089(13) 0.034(7) 0.021(8) 0.015(10) 0.091(14)
C13 0.086(14) 0.107(14) 0.034(7) -0.008(8) 0.006(8) 0.026(12)
C14 0.069(11) 0.100(12) 0.028(6) 0.002(7) 0.012(7) 0.059(10)
C15 0.087(15) 0.125(16) 0.051(8) 0.011(10) 0.031(9) 0.008(12)
C16 0.15(2) 0.107(15) 0.051(9) 0.010(9) 0.014(11) 0.097(15)
C17 0.111(16) 0.121(16) 0.040(8) 0.014(9) 0.002(9) 0.059(13)
C18 0.17(2) 0.103(15) 0.038(8) 0.009(9) 0.001(11) 0.054(15)
C19 0.135(17) 0.108(14) 0.025(6) -0.003(7) 0.008(8) 0.093(13)
C20 0.18(2) 0.101(14) 0.026(7) 0.005(8) 0.035(10) 0.042(14)
C21 0.084(14) 0.112(15) 0.058(9) 0.035(9) 0.011(9) 0.041(13)
C22 0.199(19) 0.052(9) 0.066(9) 0.012(8) 0.094(12) 0.010(12)
C23 0.078(12) 0.116(13) 0.052(8) 0.029(9) 0.010(9) 0.016(10)
C24 0.153(17) 0.093(13) 0.072(10) 0.020(9) 0.060(11) 0.001(12)
C25 0.086(12) 0.058(9) 0.026(6) -0.012(6) 0.007(7) -0.031(8)
O25 0.164(12) 0.052(6) 0.027(4) 0.022(4) 0.018(6) 0.015(7)
O26 0.131(10) 0.044(6) 0.036(5) 0.001(4) 0.006(6) 0.005(6)
C27 0.122(16) 0.098(13) 0.041(7) 0.017(8) 0.033(9) 0.033(12)
C31 0.075(10) 0.032(6) 0.025(5) 0.008(5) 0.009(6) 0.024(7)
C32 0.065(10) 0.054(8) 0.035(6) 0.013(6) 0.020(7) 0.010(7)
C33 0.095(13) 0.055(9) 0.045(7) 0.018(7) 0.028(8) 0.021(9)
C34 0.067(12) 0.095(12) 0.051(8) 0.037(8) 0.033(8) 0.041(10)
C35 0.081(12) 0.072(10) 0.050(8) 0.035(7) 0.027(8) 0.028(9)
C36 0.087(12) 0.049(8) 0.043(7) 0.023(6) 0.027(8) 0.029(8)
O31 0.118(9) 0.044(6) 0.030(4) 0.004(4) 0.027(5) 0.006(5)
O32 0.101(8) 0.038(5) 0.029(4) 0.002(4) 0.013(5) 0.009(5)
N34 0.140(14) 0.082(11) 0.076(9) 0.050(8) 0.062(9) 0.070(10)
O34 0.141(12) 0.119(12) 0.073(7) 0.035(7) 0.048(8) 0.074(10)
O35 0.182(14) 0.163(13) 0.047(6) 0.043(7) 0.062(8) 0.112(12)
C37 0.118(14) 0.041(8) 0.045(7) -0.012(6) 0.021(8) 0.006(8)

_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 O26 2.012(9) 2_645 ?
Zn1 O25 2.019(11) . ?
Zn1 O31 2.037(9) . ?
Zn1 Cl1 2.296(7) . ?
N11 C12 1.430(18) . ?
N11 C19 1.445(15) . ?
N11 C22 1.500(16) . ?
C12 C27 1.502(5) . ?
C12 C13 1.57(2) . ?
C13 C14 1.505(5) . ?
C13 C21 1.541(5) . ?
C13 C20 1.544(5) . ?
C14 C15 1.3900 . ?
C14 C19 1.3900 . ?
C15 C16 1.3900 . ?
C15 H15 0.9500 . ?
C16 C17 1.3900 . ?
C16 H16 0.9500 . ?
C17 C18 1.3900 . ?
C17 H17 0.9500 . ?
C18 C19 1.3900 . ?
C18 H18 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.538(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.548(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.544(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 O26 1.298(15) . ?
C25 O25 1.328(16) . ?
O26 Zn1 2.012(9) 2_655 ?
C27 C28 1.543(5) . ?
C27 H27 0.9500 . ?
C28 C36 1.497(5) . ?
C28 H28 0.9500 . ?
C31 O31 1.327(13) . ?
C31 C36 1.431(15) . ?
C31 C32 1.485(18) . ?
C32 O32 1.376(14) . ?
C32 C33 1.435(18) . ?
C33 C34 1.453(19) . ?
C33 H33 0.9500 . ?
C34 C35 1.39(2) . ?
C34 N34 1.476(18) . ?
C35 C36 1.453(17) . ?
C35 H35 0.9500 . ?
O32 C37 1.462(17) . ?
N34 O35 1.223(17) . ?
N34 O34 1.324(18) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?

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
O26 Zn1 O25 107.2(4) 2_645 . ?
O26 Zn1 O31 117.6(4) 2_645 . ?
O25 Zn1 O31 86.4(4) . . ?
O26 Zn1 Cl1 118.6(4) 2_645 . ?
O25 Zn1 Cl1 112.3(4) . . ?
O31 Zn1 Cl1 110.2(3) . . ?
C12 N11 C19 108.6(10) . . ?
C12 N11 C22 131.3(12) . . ?
C19 N11 C22 119.9(11) . . ?
N11 C12 C27 119.4(11) . . ?
N11 C12 C13 106.7(9) . . ?
C27 C12 C13 133.8(11) . . ?
C14 C13 C21 112.4(12) . . ?
C14 C13 C20 114.4(11) . . ?
C21 C13 C20 105.6(13) . . ?
C14 C13 C12 104.3(9) . . ?
C21 C13 C12 109.5(13) . . ?
C20 C13 C12 110.6(12) . . ?
C15 C14 C19 120.0 . . ?
C15 C14 C13 131.9(8) . . ?
C19 C14 C13 108.1(8) . . ?
C16 C15 C14 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C14 120.0 . . ?
C18 C19 N11 127.8(8) . . ?
C14 C19 N11 112.2(7) . . ?
C13 C20 H20A 109.5 . . ?
C13 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C13 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C13 C21 H21A 109.5 . . ?
C13 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C13 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N11 C22 C23 115.6(12) . . ?
N11 C22 H22A 108.4 . . ?
C23 C22 H22A 108.4 . . ?
N11 C22 H22B 108.4 . . ?
C23 C22 H22B 108.4 . . ?
H22A C22 H22B 107.4 . . ?
C22 C23 C24 108.0(14) . . ?
C22 C23 H23A 110.1 . . ?
C24 C23 H23A 110.1 . . ?
C22 C23 H23B 110.1 . . ?
C24 C23 H23B 110.1 . . ?
H23A C23 H23B 108.4 . . ?
C25 C24 C23 120.6(13) . . ?
C25 C24 H24A 107.2 . . ?
C23 C24 H24A 107.2 . . ?
C25 C24 H24B 107.2 . . ?
C23 C24 H24B 107.2 . . ?
H24A C24 H24B 106.8 . . ?
O26 C25 O25 121.9(13) . . ?
O26 C25 C24 120.7(11) . . ?
O25 C25 C24 117.2(12) . . ?
C25 O25 Zn1 141.2(9) . . ?
C25 O26 Zn1 129.9(10) . 2_655 ?
C12 C27 C28 119.8(10) . . ?
C12 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C36 C28 C27 115.1(9) . . ?
C36 C28 H28 122.5 . . ?
C27 C28 H28 122.5 . . ?
O31 C31 C36 120.6(10) . . ?
O31 C31 C32 118.1(9) . . ?
C36 C31 C32 120.4(9) . . ?
O32 C32 C33 126.4(12) . . ?
O32 C32 C31 114.9(10) . . ?
C33 C32 C31 118.6(11) . . ?
C32 C33 C34 119.5(13) . . ?
C32 C33 H33 120.2 . . ?
C34 C33 H33 120.2 . . ?
C35 C34 C33 121.1(12) . . ?
C35 C34 N34 121.7(13) . . ?
C33 C34 N34 117.1(13) . . ?
C34 C35 C36 121.7(12) . . ?
C34 C35 H35 119.2 . . ?
C36 C35 H35 119.2 . . ?
C31 C36 C35 118.5(10) . . ?
C31 C36 C28 130.1(10) . . ?
C35 C36 C28 111.4(10) . . ?
C31 O31 Zn1 128.2(9) . . ?
C32 O32 C37 119.7(10) . . ?
O35 N34 O34 121.9(12) . . ?
O35 N34 C34 119.9(13) . . ?
O34 N34 C34 118.1(13) . . ?
O32 C37 H37A 109.5 . . ?
O32 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
O32 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?

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
C19 N11 C12 C27 173.2(19) . . . . ?
C22 N11 C12 C27 -1(3) . . . . ?
C19 N11 C12 C13 -3(2) . . . . ?
C22 N11 C12 C13 -177.4(16) . . . . ?
N11 C12 C13 C14 3(2) . . . . ?
C27 C12 C13 C14 -173(2) . . . . ?
N11 C12 C13 C21 123.7(15) . . . . ?
C27 C12 C13 C21 -52(3) . . . . ?
N11 C12 C13 C20 -120.4(16) . . . . ?
C27 C12 C13 C20 64(3) . . . . ?
C21 C13 C14 C15 60.6(15) . . . . ?
C20 C13 C14 C15 -59.8(18) . . . . ?
C12 C13 C14 C15 179.2(13) . . . . ?
C21 C13 C14 C19 -120.3(12) . . . . ?
C20 C13 C14 C19 119.2(12) . . . . ?
C12 C13 C14 C19 -1.7(15) . . . . ?
C19 C14 C15 C16 0.0 . . . . ?
C13 C14 C15 C16 179.0(15) . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C17 C18 C19 C14 0.0 . . . . ?
C17 C18 C19 N11 -178.8(15) . . . . ?
C15 C14 C19 C18 0.0 . . . . ?
C13 C14 C19 C18 -179.2(12) . . . . ?
C15 C14 C19 N11 178.9(13) . . . . ?
C13 C14 C19 N11 -0.2(13) . . . . ?
C12 N11 C19 C18 -178.8(13) . . . . ?
C22 N11 C19 C18 -4(2) . . . . ?
C12 N11 C19 C14 2.3(18) . . . . ?
C22 N11 C19 C14 177.2(12) . . . . ?
C12 N11 C22 C23 84(3) . . . . ?
C19 N11 C22 C23 -89.4(19) . . . . ?
N11 C22 C23 C24 -173.4(13) . . . . ?
C22 C23 C24 C25 77(2) . . . . ?
C23 C24 C25 O26 177.8(16) . . . . ?
C23 C24 C25 O25 3(3) . . . . ?
O26 C25 O25 Zn1 -5(2) . . . . ?
C24 C25 O25 Zn1 169.5(15) . . . . ?
O26 Zn1 O25 C25 -53.6(17) 2_645 . . . ?
O31 Zn1 O25 C25 -171.4(16) . . . . ?
Cl1 Zn1 O25 C25 78.3(16) . . . . ?
O25 C25 O26 Zn1 177.8(10) . . . 2_655 ?
C24 C25 O26 Zn1 4(2) . . . 2_655 ?
N11 C12 C27 C28 -176.8(17) . . . . ?
C13 C12 C27 C28 -1(4) . . . . ?
C12 C27 C28 C36 -177.3(17) . . . . ?
O31 C31 C32 O32 7.4(19) . . . . ?
C36 C31 C32 O32 176.6(14) . . . . ?
O31 C31 C32 C33 -174.0(13) . . . . ?
C36 C31 C32 C33 -5(2) . . . . ?
O32 C32 C33 C34 -179.1(14) . . . . ?
C31 C32 C33 C34 2(2) . . . . ?
C32 C33 C34 C35 0(2) . . . . ?
C32 C33 C34 N34 -178.8(15) . . . . ?
C33 C34 C35 C36 -1(2) . . . . ?
N34 C34 C35 C36 178.3(16) . . . . ?
O31 C31 C36 C35 173.2(14) . . . . ?
C32 C31 C36 C35 4(2) . . . . ?
O31 C31 C36 C28 -4(2) . . . . ?
C32 C31 C36 C28 -173.1(15) . . . . ?
C34 C35 C36 C31 -1(2) . . . . ?
C34 C35 C36 C28 176.3(15) . . . . ?
C27 C28 C36 C31 -16(2) . . . . ?
C27 C28 C36 C35 167.0(14) . . . . ?
C36 C31 O31 Zn1 153.4(11) . . . . ?
C32 C31 O31 Zn1 -37.3(17) . . . . ?
O26 Zn1 O31 C31 92.6(11) 2_645 . . . ?
O25 Zn1 O31 C31 -159.9(11) . . . . ?
Cl1 Zn1 O31 C31 -47.5(11) . . . . ?
C33 C32 O32 C37 -2(2) . . . . ?
C31 C32 O32 C37 176.0(13) . . . . ?
C35 C34 N34 O35 -10(3) . . . . ?
C33 C34 N34 O35 169.4(17) . . . . ?
C35 C34 N34 O34 167.1(17) . . . . ?
C33 C34 N34 O34 -14(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.946
_diffrn_reflns_theta_full        28.92
_diffrn_measured_fraction_theta_full 0.946
_refine_diff_density_max         2.306
_refine_diff_density_min         -1.021
_refine_diff_density_rms         0.174