# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2010

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'R E Mulvey'
_publ_contact_author_email       R.E.MULVEY@STRATH.AC.UK

_publ_section_title              
;
Structural elaboration of the surprising
ortho-zincation of benzylmethylether
;
loop_
_publ_author_name
'R E Mulvey'
'Liam Balloch'
'Alan R. Kennedy'
'Jan Klett'
"Charles T. O'Hara"

# Attachment 'updated_bme.CIF'

data_jkliam2
_database_code_depnum_ccdc_archive 'CCDC 755821'
#TrackingRef 'updated_bme.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H52 N3 Na O Zn'
_chemical_formula_weight         523.08

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'
Na Na 0.0362 0.0249 '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)

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

_cell_length_a                   9.236(2)
_cell_length_b                   16.527(2)
_cell_length_c                   10.6095(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.39(3)
_cell_angle_gamma                90.00
_cell_volume                     1475.0(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    1416
_cell_measurement_theta_min      2.7114
_cell_measurement_theta_max      30.8334

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78402
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(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  'OXFORD DIFFRACTION GEMINI S'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean .
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13428
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0464
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         31.09
_reflns_number_total             7511
_reflns_number_gt                6567
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'CrysAlis CCD'
_computing_cell_refinement       'CrysAlis CCD'
_computing_data_reduction        'CrysAlis RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'shelxp / ortep'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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^)+(0.0352P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.052(7)
_refine_ls_number_reflns         7511
_refine_ls_number_parameters     311
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0658
_refine_ls_wR_factor_gt          0.0646
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.973
_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
Na1 Na 0.37373(10) 0.19320(5) 0.65566(8) 0.01832(16) Uani 1 1 d . . .
Zn1 Zn 0.67420(2) 0.294437(14) 0.854336(18) 0.01594(5) Uani 1 1 d . . .
C11 C 0.5958(2) 0.31964(10) 0.64592(18) 0.0172(3) Uani 1 1 d . . .
C12 C 0.4614(2) 0.36406(10) 0.5582(2) 0.0181(4) Uani 1 1 d . . .
C13 C 0.4357(2) 0.38500(11) 0.4223(2) 0.0224(4) Uani 1 1 d . . .
H13A H 0.3428 0.4143 0.3662 0.027 Uiso 1 1 calc R . .
C14 C 0.5444(3) 0.36340(11) 0.3692(2) 0.0225(4) Uani 1 1 d . . .
H14A H 0.5276 0.3780 0.2775 0.027 Uiso 1 1 calc R . .
C15 C 0.6779(2) 0.32013(11) 0.4523(2) 0.0226(4) Uani 1 1 d . . .
H15A H 0.7542 0.3049 0.4180 0.027 Uiso 1 1 calc R . .
C16 C 0.70073(19) 0.29886(16) 0.58560(16) 0.0197(3) Uani 1 1 d . . .
H16A H 0.7928 0.2684 0.6395 0.024 Uiso 1 1 calc R . .
C1 C 0.3400(3) 0.39137(13) 0.6101(2) 0.0214(4) Uani 1 1 d . . .
H1A H 0.3940 0.4177 0.7016 0.026 Uiso 1 1 calc R . .
H1B H 0.2670 0.4312 0.5451 0.026 Uiso 1 1 calc R . .
O1 O 0.25143(16) 0.32226(8) 0.62170(14) 0.0223(3) Uani 1 1 d . . .
C10 C 0.1234(3) 0.34697(14) 0.6542(3) 0.0332(5) Uani 1 1 d . . .
H10A H 0.0765 0.2994 0.6781 0.050 Uiso 1 1 calc R . .
H10B H 0.0425 0.3742 0.5740 0.050 Uiso 1 1 calc R . .
H10C H 0.1629 0.3843 0.7330 0.050 Uiso 1 1 calc R . .
C2 C 0.8502(2) 0.36841(11) 0.9821(2) 0.0231(4) Uani 1 1 d . . .
C21 C 0.9810(3) 0.37131(15) 0.9280(3) 0.0411(6) Uani 1 1 d . . .
H21A H 1.0603 0.4122 0.9796 0.062 Uiso 1 1 calc R . .
H21B H 0.9338 0.3854 0.8294 0.062 Uiso 1 1 calc R . .
H21C H 1.0323 0.3182 0.9403 0.062 Uiso 1 1 calc R . .
C22 C 0.9240(3) 0.34555(14) 1.1346(2) 0.0385(6) Uani 1 1 d . . .
H22A H 1.0067 0.3849 1.1863 0.058 Uiso 1 1 calc R . .
H22B H 0.9713 0.2915 1.1454 0.058 Uiso 1 1 calc R . .
H22C H 0.8417 0.3455 1.1704 0.058 Uiso 1 1 calc R . .
C23 C 0.7834(3) 0.45356(12) 0.9694(2) 0.0311(5) Uani 1 1 d . . .
H23A H 0.8699 0.4915 1.0185 0.047 Uiso 1 1 calc R . .
H23B H 0.7055 0.4553 1.0101 0.047 Uiso 1 1 calc R . .
H23C H 0.7316 0.4687 0.8715 0.047 Uiso 1 1 calc R . .
N3 N 0.57605(18) 0.19533(9) 0.89675(15) 0.0160(3) Uani 1 1 d . . .
C32 C 0.6732(2) 0.12091(11) 0.92260(19) 0.0188(4) Uani 1 1 d . . .
C321 C 0.5749(3) 0.04432(11) 0.8563(2) 0.0248(4) Uani 1 1 d . . .
H32A H 0.5111 0.0540 0.7575 0.037 Uiso 1 1 calc R . .
H32B H 0.5044 0.0318 0.9018 0.037 Uiso 1 1 calc R . .
H32C H 0.6469 -0.0013 0.8674 0.037 Uiso 1 1 calc R . .
C322 C 0.7883(3) 0.13215(12) 0.8521(2) 0.0253(4) Uani 1 1 d . . .
H32D H 0.7273 0.1433 0.7534 0.038 Uiso 1 1 calc R . .
H32E H 0.8509 0.0827 0.8630 0.038 Uiso 1 1 calc R . .
H32F H 0.8599 0.1776 0.8951 0.038 Uiso 1 1 calc R . .
C33 C 0.7738(2) 0.10399(13) 1.0766(2) 0.0244(4) Uani 1 1 d . . .
H33A H 0.8239 0.0500 1.0867 0.029 Uiso 1 1 calc R . .
H33B H 0.8597 0.1448 1.1133 0.029 Uiso 1 1 calc R . .
C34 C 0.6738(2) 0.10656(13) 1.1609(2) 0.0272(4) Uani 1 1 d . . .
H34A H 0.5901 0.0645 1.1278 0.033 Uiso 1 1 calc R . .
H34B H 0.7417 0.0963 1.2598 0.033 Uiso 1 1 calc R . .
C36 C 0.4949(2) 0.21012(11) 0.99091(19) 0.0186(4) Uani 1 1 d . . .
C35 C 0.5991(2) 0.18994(13) 1.14293(19) 0.0241(4) Uani 1 1 d . . .
H35A H 0.6843 0.2310 1.1809 0.029 Uiso 1 1 calc R . .
H35B H 0.5334 0.1929 1.1966 0.029 Uiso 1 1 calc R . .
C361 C 0.3368(2) 0.16450(12) 0.9464(2) 0.0245(4) Uani 1 1 d . . .
H36A H 0.3571 0.1061 0.9552 0.037 Uiso 1 1 calc R . .
H36B H 0.2684 0.1777 0.8499 0.037 Uiso 1 1 calc R . .
H36C H 0.2838 0.1806 1.0057 0.037 Uiso 1 1 calc R . .
C362 C 0.4553(2) 0.30044(16) 0.98252(18) 0.0246(4) Uani 1 1 d . . .
H36D H 0.5540 0.3318 1.0233 0.037 Uiso 1 1 calc R . .
H36E H 0.3898 0.3113 1.0335 0.037 Uiso 1 1 calc R . .
H36F H 0.3968 0.3161 0.8854 0.037 Uiso 1 1 calc R . .
N41 N 0.11792(19) 0.09431(10) 0.57411(16) 0.0209(3) Uani 1 1 d . . .
C411 C -0.0241(3) 0.13287(15) 0.5748(2) 0.0337(5) Uani 1 1 d . . .
H41A H -0.0058 0.1467 0.6700 0.051 Uiso 1 1 calc R . .
H41B H -0.1143 0.0955 0.5362 0.051 Uiso 1 1 calc R . .
H41C H -0.0476 0.1822 0.5186 0.051 Uiso 1 1 calc R . .
C412 C 0.1462(3) 0.01931(13) 0.6552(2) 0.0273(4) Uani 1 1 d . . .
H41D H 0.1659 0.0324 0.7510 0.041 Uiso 1 1 calc R . .
H41E H 0.2389 -0.0087 0.6535 0.041 Uiso 1 1 calc R . .
H41F H 0.0526 -0.0158 0.6151 0.041 Uiso 1 1 calc R . .
C42 C 0.0911(2) 0.07499(12) 0.43067(19) 0.0223(4) Uani 1 1 d . . .
H42A H 0.0395 0.1220 0.3711 0.027 Uiso 1 1 calc R . .
H42B H 0.0167 0.0287 0.3985 0.027 Uiso 1 1 calc R . .
C43 C 0.2402(2) 0.05424(11) 0.4123(2) 0.0216(4) Uani 1 1 d . . .
H43A H 0.2957 0.0094 0.4759 0.026 Uiso 1 1 calc R . .
H43B H 0.2105 0.0350 0.3165 0.026 Uiso 1 1 calc R . .
N44 N 0.34994(19) 0.12313(9) 0.43931(16) 0.0189(3) Uani 1 1 d . . .
C441 C 0.2827(3) 0.18507(13) 0.3316(2) 0.0288(4) Uani 1 1 d . . .
H44A H 0.1887 0.2091 0.3376 0.043 Uiso 1 1 calc R . .
H44B H 0.2522 0.1602 0.2403 0.043 Uiso 1 1 calc R . .
H44C H 0.3622 0.2273 0.3449 0.043 Uiso 1 1 calc R . .
C442 C 0.4998(3) 0.09464(13) 0.4388(2) 0.0270(4) Uani 1 1 d . . .
H44D H 0.5469 0.0538 0.5112 0.040 Uiso 1 1 calc R . .
H44E H 0.5733 0.1403 0.4564 0.040 Uiso 1 1 calc R . .
H44F H 0.4795 0.0708 0.3485 0.040 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
Na1 0.0185(4) 0.0207(4) 0.0141(4) -0.0018(3) 0.0051(3) 0.0016(3)
Zn1 0.01556(9) 0.01842(8) 0.01512(9) -0.00162(10) 0.00760(6) -0.00060(10)
C11 0.0179(9) 0.0154(8) 0.0196(9) -0.0016(6) 0.0090(7) -0.0037(6)
C12 0.0213(9) 0.0138(8) 0.0217(9) -0.0011(7) 0.0115(7) -0.0032(7)
C13 0.0232(10) 0.0184(9) 0.0210(9) 0.0010(7) 0.0045(8) -0.0019(7)
C14 0.0314(11) 0.0214(9) 0.0160(9) -0.0003(7) 0.0110(8) -0.0079(8)
C15 0.0253(10) 0.0241(9) 0.0236(9) -0.0044(7) 0.0155(8) -0.0065(7)
C16 0.0195(8) 0.0200(8) 0.0210(8) -0.0010(10) 0.0096(6) -0.0021(10)
C1 0.0229(11) 0.0147(9) 0.0291(11) 0.0033(8) 0.0134(9) 0.0015(8)
O1 0.0182(7) 0.0208(6) 0.0321(7) 0.0028(5) 0.0147(6) 0.0021(5)
C10 0.0243(11) 0.0318(11) 0.0504(14) 0.0067(10) 0.0224(10) 0.0050(9)
C2 0.0204(10) 0.0251(9) 0.0248(10) -0.0063(8) 0.0105(8) -0.0066(7)
C21 0.0271(12) 0.0451(14) 0.0576(16) -0.0200(12) 0.0240(11) -0.0123(10)
C22 0.0330(13) 0.0349(12) 0.0317(12) -0.0027(10) -0.0026(10) -0.0093(10)
C23 0.0415(14) 0.0224(10) 0.0350(12) -0.0079(9) 0.0212(10) -0.0081(9)
N3 0.0178(7) 0.0187(7) 0.0125(7) 0.0004(6) 0.0073(6) 0.0006(6)
C32 0.0189(9) 0.0213(9) 0.0151(9) 0.0003(7) 0.0059(7) 0.0000(7)
C321 0.0267(11) 0.0210(9) 0.0249(10) -0.0002(8) 0.0089(8) 0.0026(8)
C322 0.0258(11) 0.0261(10) 0.0257(10) 0.0018(8) 0.0124(8) 0.0065(8)
C33 0.0217(10) 0.0287(10) 0.0193(10) 0.0048(8) 0.0050(8) 0.0038(8)
C34 0.0244(10) 0.0374(11) 0.0152(9) 0.0066(8) 0.0037(8) -0.0030(9)
C36 0.0202(9) 0.0238(9) 0.0136(8) -0.0014(7) 0.0086(7) -0.0017(7)
C35 0.0238(10) 0.0360(10) 0.0139(9) -0.0023(8) 0.0094(8) -0.0047(8)
C361 0.0217(10) 0.0322(10) 0.0224(10) -0.0008(8) 0.0119(8) -0.0038(8)
C362 0.0265(9) 0.0293(10) 0.0233(8) -0.0032(11) 0.0157(7) 0.0014(11)
N41 0.0189(8) 0.0254(8) 0.0194(8) -0.0008(6) 0.0088(6) -0.0004(6)
C411 0.0225(11) 0.0439(13) 0.0355(12) -0.0049(10) 0.0129(9) 0.0059(9)
C412 0.0313(12) 0.0267(10) 0.0227(10) 0.0009(8) 0.0098(9) -0.0066(9)
C42 0.0196(10) 0.0260(9) 0.0182(9) -0.0011(8) 0.0047(8) -0.0061(8)
C43 0.0288(11) 0.0198(9) 0.0181(9) -0.0029(7) 0.0118(8) -0.0039(8)
N44 0.0232(8) 0.0181(7) 0.0192(8) -0.0006(6) 0.0126(6) -0.0012(6)
C441 0.0345(12) 0.0241(10) 0.0289(11) 0.0051(9) 0.0142(9) -0.0034(9)
C442 0.0277(11) 0.0273(10) 0.0321(11) -0.0017(9) 0.0185(9) -0.0002(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
Na1 O1 2.3705(15) . ?
Na1 N3 2.4675(19) . ?
Na1 N44 2.4983(17) . ?
Na1 N41 2.7043(19) . ?
Na1 C11 2.9597(19) . ?
Na1 Zn1 3.1802(13) . ?
Zn1 N3 2.0109(15) . ?
Zn1 C2 2.038(2) . ?
Zn1 C11 2.0652(18) . ?
C11 C16 1.406(2) . ?
C11 C12 1.411(3) . ?
C12 C13 1.404(3) . ?
C12 C1 1.509(3) . ?
C13 C14 1.386(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.386(2) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C1 O1 1.439(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
O1 C10 1.422(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C2 C23 1.520(3) . ?
C2 C22 1.522(3) . ?
C2 C21 1.538(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
N3 C32 1.480(2) . ?
N3 C36 1.496(2) . ?
C32 C33 1.535(3) . ?
C32 C322 1.543(3) . ?
C32 C321 1.547(3) . ?
C321 H32A 0.9800 . ?
C321 H32B 0.9800 . ?
C321 H32C 0.9800 . ?
C322 H32D 0.9800 . ?
C322 H32E 0.9800 . ?
C322 H32F 0.9800 . ?
C33 C34 1.529(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.518(3) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C36 C362 1.531(3) . ?
C36 C361 1.535(3) . ?
C36 C35 1.535(3) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C361 H36A 0.9800 . ?
C361 H36B 0.9800 . ?
C361 H36C 0.9800 . ?
C362 H36D 0.9800 . ?
C362 H36E 0.9800 . ?
C362 H36F 0.9800 . ?
N41 C411 1.461(3) . ?
N41 C412 1.469(3) . ?
N41 C42 1.472(2) . ?
C411 H41A 0.9800 . ?
C411 H41B 0.9800 . ?
C411 H41C 0.9800 . ?
C412 H41D 0.9800 . ?
C412 H41E 0.9800 . ?
C412 H41F 0.9800 . ?
C42 C43 1.508(3) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 N44 1.471(2) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
N44 C442 1.464(2) . ?
N44 C441 1.468(2) . ?
C441 H44A 0.9800 . ?
C441 H44B 0.9800 . ?
C441 H44C 0.9800 . ?
C442 H44D 0.9800 . ?
C442 H44E 0.9800 . ?
C442 H44F 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
O1 Na1 N3 104.72(6) . . ?
O1 Na1 N44 114.95(6) . . ?
N3 Na1 N44 134.48(6) . . ?
O1 Na1 N41 101.34(6) . . ?
N3 Na1 N41 121.87(6) . . ?
N44 Na1 N41 72.07(6) . . ?
O1 Na1 C11 69.70(5) . . ?
N3 Na1 C11 77.70(6) . . ?
N44 Na1 C11 95.42(6) . . ?
N41 Na1 C11 160.39(6) . . ?
O1 Na1 Zn1 81.83(4) . . ?
N3 Na1 Zn1 39.22(4) . . ?
N44 Na1 Zn1 125.06(5) . . ?
N41 Na1 Zn1 159.72(4) . . ?
C11 Na1 Zn1 39.10(4) . . ?
N3 Zn1 C2 130.48(7) . . ?
N3 Zn1 C11 114.38(6) . . ?
C2 Zn1 C11 114.94(8) . . ?
N3 Zn1 Na1 50.89(5) . . ?
C2 Zn1 Na1 173.93(6) . . ?
C11 Zn1 Na1 64.68(5) . . ?
C16 C11 C12 114.23(16) . . ?
C16 C11 Zn1 115.80(13) . . ?
C12 C11 Zn1 129.43(13) . . ?
C16 C11 Na1 117.46(13) . . ?
C12 C11 Na1 87.52(11) . . ?
Zn1 C11 Na1 76.22(6) . . ?
C13 C12 C11 122.37(17) . . ?
C13 C12 C1 117.72(18) . . ?
C11 C12 C1 119.92(17) . . ?
C14 C13 C12 120.67(18) . . ?
C14 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
C15 C14 C13 118.61(17) . . ?
C15 C14 H14A 120.7 . . ?
C13 C14 H14A 120.7 . . ?
C14 C15 C16 120.10(17) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C15 C16 C11 124.01(18) . . ?
C15 C16 H16A 118.0 . . ?
C11 C16 H16A 118.0 . . ?
O1 C1 C12 109.15(16) . . ?
O1 C1 H1A 109.8 . . ?
C12 C1 H1A 109.8 . . ?
O1 C1 H1B 109.8 . . ?
C12 C1 H1B 109.8 . . ?
H1A C1 H1B 108.3 . . ?
C10 O1 C1 110.59(15) . . ?
C10 O1 Na1 127.84(12) . . ?
C1 O1 Na1 118.37(11) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C23 C2 C22 108.13(17) . . ?
C23 C2 C21 106.93(17) . . ?
C22 C2 C21 109.2(2) . . ?
C23 C2 Zn1 108.25(14) . . ?
C22 C2 Zn1 116.25(14) . . ?
C21 C2 Zn1 107.71(14) . . ?
C2 C21 H21A 109.5 . . ?
C2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C2 C22 H22A 109.5 . . ?
C2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C2 C23 H23A 109.5 . . ?
C2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C32 N3 C36 116.40(14) . . ?
C32 N3 Zn1 115.07(11) . . ?
C36 N3 Zn1 114.38(11) . . ?
C32 N3 Na1 108.78(11) . . ?
C36 N3 Na1 108.71(11) . . ?
Zn1 N3 Na1 89.89(6) . . ?
N3 C32 C33 113.75(15) . . ?
N3 C32 C322 107.24(14) . . ?
C33 C32 C322 107.61(16) . . ?
N3 C32 C321 113.50(15) . . ?
C33 C32 C321 108.58(15) . . ?
C322 C32 C321 105.69(15) . . ?
C32 C321 H32A 109.5 . . ?
C32 C321 H32B 109.5 . . ?
H32A C321 H32B 109.5 . . ?
C32 C321 H32C 109.5 . . ?
H32A C321 H32C 109.5 . . ?
H32B C321 H32C 109.5 . . ?
C32 C322 H32D 109.5 . . ?
C32 C322 H32E 109.5 . . ?
H32D C322 H32E 109.5 . . ?
C32 C322 H32F 109.5 . . ?
H32D C322 H32F 109.5 . . ?
H32E C322 H32F 109.5 . . ?
C34 C33 C32 111.81(16) . . ?
C34 C33 H33A 109.3 . . ?
C32 C33 H33A 109.3 . . ?
C34 C33 H33B 109.3 . . ?
C32 C33 H33B 109.3 . . ?
H33A C33 H33B 107.9 . . ?
C35 C34 C33 107.75(16) . . ?
C35 C34 H34A 110.2 . . ?
C33 C34 H34A 110.2 . . ?
C35 C34 H34B 110.2 . . ?
C33 C34 H34B 110.2 . . ?
H34A C34 H34B 108.5 . . ?
N3 C36 C362 107.09(14) . . ?
N3 C36 C361 112.94(15) . . ?
C362 C36 C361 106.70(16) . . ?
N3 C36 C35 113.36(15) . . ?
C362 C36 C35 107.70(15) . . ?
C361 C36 C35 108.70(15) . . ?
C34 C35 C36 112.62(16) . . ?
C34 C35 H35A 109.1 . . ?
C36 C35 H35A 109.1 . . ?
C34 C35 H35B 109.1 . . ?
C36 C35 H35B 109.1 . . ?
H35A C35 H35B 107.8 . . ?
C36 C361 H36A 109.5 . . ?
C36 C361 H36B 109.5 . . ?
H36A C361 H36B 109.5 . . ?
C36 C361 H36C 109.5 . . ?
H36A C361 H36C 109.5 . . ?
H36B C361 H36C 109.5 . . ?
C36 C362 H36D 109.5 . . ?
C36 C362 H36E 109.5 . . ?
H36D C362 H36E 109.5 . . ?
C36 C362 H36F 109.5 . . ?
H36D C362 H36F 109.5 . . ?
H36E C362 H36F 109.5 . . ?
C411 N41 C412 107.94(16) . . ?
C411 N41 C42 109.34(16) . . ?
C412 N41 C42 109.60(15) . . ?
C411 N41 Na1 113.74(13) . . ?
C412 N41 Na1 113.70(12) . . ?
C42 N41 Na1 102.35(11) . . ?
N41 C411 H41A 109.5 . . ?
N41 C411 H41B 109.5 . . ?
H41A C411 H41B 109.5 . . ?
N41 C411 H41C 109.5 . . ?
H41A C411 H41C 109.5 . . ?
H41B C411 H41C 109.5 . . ?
N41 C412 H41D 109.5 . . ?
N41 C412 H41E 109.5 . . ?
H41D C412 H41E 109.5 . . ?
N41 C412 H41F 109.5 . . ?
H41D C412 H41F 109.5 . . ?
H41E C412 H41F 109.5 . . ?
N41 C42 C43 114.18(16) . . ?
N41 C42 H42A 108.7 . . ?
C43 C42 H42A 108.7 . . ?
N41 C42 H42B 108.7 . . ?
C43 C42 H42B 108.7 . . ?
H42A C42 H42B 107.6 . . ?
N44 C43 C42 113.03(15) . . ?
N44 C43 H43A 109.0 . . ?
C42 C43 H43A 109.0 . . ?
N44 C43 H43B 109.0 . . ?
C42 C43 H43B 109.0 . . ?
H43A C43 H43B 107.8 . . ?
C442 N44 C441 108.56(15) . . ?
C442 N44 C43 109.06(15) . . ?
C441 N44 C43 110.62(16) . . ?
C442 N44 Na1 115.33(13) . . ?
C441 N44 Na1 103.91(12) . . ?
C43 N44 Na1 109.25(10) . . ?
N44 C441 H44A 109.5 . . ?
N44 C441 H44B 109.5 . . ?
H44A C441 H44B 109.5 . . ?
N44 C441 H44C 109.5 . . ?
H44A C441 H44C 109.5 . . ?
H44B C441 H44C 109.5 . . ?
N44 C442 H44D 109.5 . . ?
N44 C442 H44E 109.5 . . ?
H44D C442 H44E 109.5 . . ?
N44 C442 H44F 109.5 . . ?
H44D C442 H44F 109.5 . . ?
H44E C442 H44F 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
O1 Na1 Zn1 N3 125.57(7) . . . . ?
N44 Na1 Zn1 N3 -119.60(8) . . . . ?
N41 Na1 Zn1 N3 24.92(14) . . . . ?
C11 Na1 Zn1 N3 -166.72(8) . . . . ?
O1 Na1 Zn1 C2 20.1(5) . . . . ?
N3 Na1 Zn1 C2 -105.5(5) . . . . ?
N44 Na1 Zn1 C2 134.9(5) . . . . ?
N41 Na1 Zn1 C2 -80.5(6) . . . . ?
C11 Na1 Zn1 C2 87.8(5) . . . . ?
O1 Na1 Zn1 C11 -67.71(6) . . . . ?
N3 Na1 Zn1 C11 166.72(8) . . . . ?
N44 Na1 Zn1 C11 47.12(7) . . . . ?
N41 Na1 Zn1 C11 -168.36(15) . . . . ?
N3 Zn1 C11 C16 -102.84(15) . . . . ?
C2 Zn1 C11 C16 72.56(16) . . . . ?
Na1 Zn1 C11 C16 -114.13(16) . . . . ?
N3 Zn1 C11 C12 86.26(16) . . . . ?
C2 Zn1 C11 C12 -98.33(17) . . . . ?
Na1 Zn1 C11 C12 74.98(16) . . . . ?
N3 Zn1 C11 Na1 11.29(7) . . . . ?
C2 Zn1 C11 Na1 -173.31(6) . . . . ?
O1 Na1 C11 C16 -145.40(14) . . . . ?
N3 Na1 C11 C16 103.63(14) . . . . ?
N44 Na1 C11 C16 -30.77(14) . . . . ?
N41 Na1 C11 C16 -79.8(2) . . . . ?
Zn1 Na1 C11 C16 112.18(15) . . . . ?
O1 Na1 C11 C12 -29.27(10) . . . . ?
N3 Na1 C11 C12 -140.24(11) . . . . ?
N44 Na1 C11 C12 85.36(11) . . . . ?
N41 Na1 C11 C12 36.3(2) . . . . ?
Zn1 Na1 C11 C12 -131.69(12) . . . . ?
O1 Na1 C11 Zn1 102.42(6) . . . . ?
N3 Na1 C11 Zn1 -8.55(5) . . . . ?
N44 Na1 C11 Zn1 -142.95(6) . . . . ?
N41 Na1 C11 Zn1 167.98(15) . . . . ?
C16 C11 C12 C13 0.3(3) . . . . ?
Zn1 C11 C12 C13 171.29(13) . . . . ?
Na1 C11 C12 C13 -118.84(16) . . . . ?
C16 C11 C12 C1 -179.17(18) . . . . ?
Zn1 C11 C12 C1 -8.2(3) . . . . ?
Na1 C11 C12 C1 61.71(16) . . . . ?
C11 C12 C13 C14 -0.9(3) . . . . ?
C1 C12 C13 C14 178.53(17) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 C11 -1.0(3) . . . . ?
C12 C11 C16 C15 0.7(3) . . . . ?
Zn1 C11 C16 C15 -171.63(16) . . . . ?
Na1 C11 C16 C15 101.1(2) . . . . ?
C13 C12 C1 O1 108.79(19) . . . . ?
C11 C12 C1 O1 -71.7(2) . . . . ?
C12 C1 O1 C10 -172.94(17) . . . . ?
C12 C1 O1 Na1 25.7(2) . . . . ?
N3 Na1 O1 C10 -85.36(17) . . . . ?
N44 Na1 O1 C10 117.53(17) . . . . ?
N41 Na1 O1 C10 42.19(17) . . . . ?
C11 Na1 O1 C10 -155.97(17) . . . . ?
Zn1 Na1 O1 C10 -117.49(17) . . . . ?
N3 Na1 O1 C1 72.39(14) . . . . ?
N44 Na1 O1 C1 -84.72(15) . . . . ?
N41 Na1 O1 C1 -160.06(13) . . . . ?
C11 Na1 O1 C1 1.79(13) . . . . ?
Zn1 Na1 O1 C1 40.27(13) . . . . ?
N3 Zn1 C2 C23 -120.47(13) . . . . ?
C11 Zn1 C2 C23 65.04(15) . . . . ?
Na1 Zn1 C2 C23 -19.9(6) . . . . ?
N3 Zn1 C2 C22 1.4(2) . . . . ?
C11 Zn1 C2 C22 -173.10(15) . . . . ?
Na1 Zn1 C2 C22 101.9(6) . . . . ?
N3 Zn1 C2 C21 124.25(15) . . . . ?
C11 Zn1 C2 C21 -50.25(17) . . . . ?
Na1 Zn1 C2 C21 -135.2(5) . . . . ?
C2 Zn1 N3 C32 -76.93(14) . . . . ?
C11 Zn1 N3 C32 97.58(13) . . . . ?
Na1 Zn1 N3 C32 110.76(13) . . . . ?
C2 Zn1 N3 C36 61.73(15) . . . . ?
C11 Zn1 N3 C36 -123.75(12) . . . . ?
Na1 Zn1 N3 C36 -110.57(13) . . . . ?
C2 Zn1 N3 Na1 172.30(7) . . . . ?
C11 Zn1 N3 Na1 -13.18(8) . . . . ?
O1 Na1 N3 C32 -172.89(10) . . . . ?
N44 Na1 N3 C32 -22.52(15) . . . . ?
N41 Na1 N3 C32 73.36(12) . . . . ?
C11 Na1 N3 C32 -108.01(11) . . . . ?
Zn1 Na1 N3 C32 -116.54(12) . . . . ?
O1 Na1 N3 C36 59.44(12) . . . . ?
N44 Na1 N3 C36 -150.18(11) . . . . ?
N41 Na1 N3 C36 -54.30(13) . . . . ?
C11 Na1 N3 C36 124.33(11) . . . . ?
Zn1 Na1 N3 C36 115.80(12) . . . . ?
O1 Na1 N3 Zn1 -56.35(6) . . . . ?
N44 Na1 N3 Zn1 94.02(9) . . . . ?
N41 Na1 N3 Zn1 -170.10(5) . . . . ?
C11 Na1 N3 Zn1 8.53(5) . . . . ?
C36 N3 C32 C33 -41.9(2) . . . . ?
Zn1 N3 C32 C33 95.90(15) . . . . ?
Na1 N3 C32 C33 -165.08(12) . . . . ?
C36 N3 C32 C322 -160.77(15) . . . . ?
Zn1 N3 C32 C322 -22.96(18) . . . . ?
Na1 N3 C32 C322 76.06(15) . . . . ?
C36 N3 C32 C321 82.89(19) . . . . ?
Zn1 N3 C32 C321 -139.30(13) . . . . ?
Na1 N3 C32 C321 -40.27(16) . . . . ?
N3 C32 C33 C34 51.4(2) . . . . ?
C322 C32 C33 C34 170.00(16) . . . . ?
C321 C32 C33 C34 -76.0(2) . . . . ?
C32 C33 C34 C35 -58.9(2) . . . . ?
C32 N3 C36 C362 159.63(15) . . . . ?
Zn1 N3 C36 C362 21.53(17) . . . . ?
Na1 N3 C36 C362 -77.17(15) . . . . ?
C32 N3 C36 C361 -83.2(2) . . . . ?
Zn1 N3 C36 C361 138.70(13) . . . . ?
Na1 N3 C36 C361 40.00(17) . . . . ?
C32 N3 C36 C35 41.0(2) . . . . ?
Zn1 N3 C36 C35 -97.10(16) . . . . ?
Na1 N3 C36 C35 164.19(13) . . . . ?
C33 C34 C35 C36 58.6(2) . . . . ?
N3 C36 C35 C34 -50.0(2) . . . . ?
C362 C36 C35 C34 -168.33(16) . . . . ?
C361 C36 C35 C34 76.43(19) . . . . ?
O1 Na1 N41 C411 -20.03(14) . . . . ?
N3 Na1 N41 C411 95.42(14) . . . . ?
N44 Na1 N41 C411 -132.82(14) . . . . ?
C11 Na1 N41 C411 -80.6(2) . . . . ?
Zn1 Na1 N41 C411 77.1(2) . . . . ?
O1 Na1 N41 C412 -144.12(12) . . . . ?
N3 Na1 N41 C412 -28.66(14) . . . . ?
N44 Na1 N41 C412 103.10(13) . . . . ?
C11 Na1 N41 C412 155.33(17) . . . . ?
Zn1 Na1 N41 C412 -46.9(2) . . . . ?
O1 Na1 N41 C42 97.78(11) . . . . ?
N3 Na1 N41 C42 -146.77(11) . . . . ?
N44 Na1 N41 C42 -15.01(11) . . . . ?
C11 Na1 N41 C42 37.2(2) . . . . ?
Zn1 Na1 N41 C42 -165.05(12) . . . . ?
C411 N41 C42 C43 165.66(17) . . . . ?
C412 N41 C42 C43 -76.22(19) . . . . ?
Na1 N41 C42 C43 44.76(16) . . . . ?
N41 C42 C43 N44 -66.3(2) . . . . ?
C42 C43 N44 C442 171.87(16) . . . . ?
C42 C43 N44 C441 -68.8(2) . . . . ?
C42 C43 N44 Na1 45.00(18) . . . . ?
O1 Na1 N44 C442 127.61(12) . . . . ?
N3 Na1 N44 C442 -20.56(16) . . . . ?
N41 Na1 N44 C442 -137.95(13) . . . . ?
C11 Na1 N44 C442 57.51(13) . . . . ?
Zn1 Na1 N44 C442 29.85(14) . . . . ?
O1 Na1 N44 C441 8.92(13) . . . . ?
N3 Na1 N44 C441 -139.26(12) . . . . ?
N41 Na1 N44 C441 103.36(12) . . . . ?
C11 Na1 N44 C441 -61.19(12) . . . . ?
Zn1 Na1 N44 C441 -88.85(12) . . . . ?
O1 Na1 N44 C43 -109.16(13) . . . . ?
N3 Na1 N44 C43 102.66(14) . . . . ?
N41 Na1 N44 C43 -14.72(12) . . . . ?
C11 Na1 N44 C43 -179.27(12) . . . . ?
Zn1 Na1 N44 C43 153.07(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.901
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.052