# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H B N O Zn'
_chemical_formula_weight         119.21

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'
B B 0.0013 0.0007 '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           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   8.670(4)
_cell_length_b                   8.670(4)
_cell_length_c                   12.722(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     956.2(12)
_cell_formula_units_Z            10
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.070
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             570
_exptl_absorpt_coefficient_mu    6.203
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5272
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.84
_diffrn_reflns_theta_max         25.09
_reflns_number_total             853
_reflns_number_gt                849
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_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)+(0.0196P)²+0.3166P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.016(17)
_refine_ls_number_reflns         853
_refine_ls_number_parameters     79
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0160
_refine_ls_R_factor_gt           0.0159
_refine_ls_wR_factor_ref         0.0482
_refine_ls_wR_factor_gt          0.0482
_refine_ls_goodness_of_fit_ref   1.242
_refine_ls_restrained_S_all      1.242
_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 0.57205(3) 0.57205(3) 0.0000 0.01678(13) Uani 1 2 d S . .
O3 O 0.43997(17) 0.70155(17) 0.12949(11) 0.0126(3) Uani 1 1 d . . .
N1 N 0.5917(2) 0.3906(2) 0.09917(14) 0.0165(4) Uani 1 1 d . . .
H1A H 0.5948 0.3033 0.0610 0.020 Uiso 1 1 d R . .
H1B H 0.5070 0.3865 0.1400 0.020 Uiso 1 1 d R . .
O1 O 0.73136(15) 0.73136(15) 0.0000 0.0112(4) Uani 1 2 d S . .
O5 O 0.49342(18) 0.7464(2) 0.31280(11) 0.0159(4) Uani 1 1 d . . .
O4 O 0.68631(17) 0.79563(18) 0.18783(11) 0.0144(3) Uani 1 1 d . . .
B1 B 0.5382(3) 0.7512(3) 0.20931(19) 0.0110(5) Uani 1 1 d . . .
C2 C 0.7367(3) 0.2633(3) 0.2500 0.0224(7) Uani 1 2 d S . .
H2A H 0.8333 0.2672 0.2867 0.027 Uiso 0.50 1 d PR . .
C1 C 0.7314(3) 0.3943(3) 0.16922(18) 0.0211(5) Uani 1 1 d . . .
H1C H 0.7328 0.4912 0.2058 0.025 Uiso 1 1 d R . .
H1D H 0.8221 0.3894 0.1261 0.025 Uiso 1 1 d R . .
B2 B 0.7722(3) 0.8296(3) 0.09273(18) 0.0102(5) Uani 1 1 d . . .

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 0.01715(14) 0.01715(14) 0.0160(2) 0.00579(11) -0.00579(11) -0.00637(16)
O3 0.0088(7) 0.0192(8) 0.0099(7) -0.0024(6) 0.0010(6) -0.0003(7)
N1 0.0224(11) 0.0147(10) 0.0124(9) -0.0004(7) 0.0015(8) 0.0029(7)
O1 0.0125(6) 0.0125(6) 0.0086(9) -0.0002(7) 0.0002(7) -0.0045(8)
O5 0.0115(8) 0.0266(9) 0.0095(8) 0.0011(6) 0.0002(6) -0.0035(8)
O4 0.0118(8) 0.0223(8) 0.0091(7) 0.0005(6) 0.0015(6) -0.0038(7)
B1 0.0128(13) 0.0101(11) 0.0102(11) 0.0006(9) -0.0003(9) 0.0003(9)
C2 0.0268(11) 0.0268(11) 0.0135(15) 0.0018(12) 0.0018(12) 0.0135(14)
C1 0.0207(13) 0.0272(14) 0.0155(11) 0.0020(10) 0.0022(10) 0.0039(10)
B2 0.0103(11) 0.0133(12) 0.0069(11) 0.0001(9) -0.0002(9) -0.0006(9)

_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 1.953(2) . ?
Zn1 N1 2.024(2) 7 ?
Zn1 N1 2.024(2) . ?
Zn1 O3 2.2989(19) 7 ?
Zn1 O3 2.2989(19) . ?
O3 B1 1.393(3) . ?
O3 B2 1.521(3) 6_465 ?
N1 C1 1.504(3) . ?
N1 H1A 0.9001 . ?
N1 H1B 0.8999 . ?
O1 B2 1.498(3) . ?
O1 B2 1.498(3) 7 ?
O5 B1 1.373(3) . ?
O5 B2 1.479(3) 4_465 ?
O4 B1 1.368(3) . ?
O4 B2 1.451(3) . ?
C2 C1 1.533(3) 8_665 ?
C2 C1 1.533(3) . ?
C2 H2A 0.9598 . ?
C1 H1C 0.9600 . ?
C1 H1D 0.9600 . ?
B2 O5 1.479(3) 3_654 ?
B2 O3 1.521(3) 6_565 ?

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 N1 119.35(6) . 7 ?
O1 Zn1 N1 119.35(6) . . ?
N1 Zn1 N1 121.29(12) 7 . ?
O1 Zn1 O3 90.39(4) . 7 ?
N1 Zn1 O3 88.55(8) 7 7 ?
N1 Zn1 O3 91.06(8) . 7 ?
O1 Zn1 O3 90.39(4) . . ?
N1 Zn1 O3 91.06(8) 7 . ?
N1 Zn1 O3 88.55(8) . . ?
O3 Zn1 O3 179.21(8) 7 . ?
B1 O3 B2 118.03(17) . 6_465 ?
B1 O3 Zn1 111.62(14) . . ?
B2 O3 Zn1 123.78(12) 6_465 . ?
C1 N1 Zn1 114.86(15) . . ?
C1 N1 H1A 108.3 . . ?
Zn1 N1 H1A 108.7 . . ?
C1 N1 H1B 108.4 . . ?
Zn1 N1 H1B 108.8 . . ?
H1A N1 H1B 107.7 . . ?
B2 O1 B2 110.6(2) . 7 ?
B2 O1 Zn1 124.72(11) . . ?
B2 O1 Zn1 124.72(11) 7 . ?
B1 O5 B2 121.44(18) . 4_465 ?
B1 O4 B2 134.88(18) . . ?
O4 B1 O5 117.7(2) . . ?
O4 B1 O3 121.0(2) . . ?
O5 B1 O3 121.1(2) . . ?
C1 C2 C1 113.9(3) 8_665 . ?
C1 C2 H2A 108.6 8_665 . ?
C1 C2 H2A 109.1 . . ?
N1 C1 C2 113.93(19) . . ?
N1 C1 H1C 108.4 . . ?
C2 C1 H1C 108.8 . . ?
N1 C1 H1D 108.7 . . ?
C2 C1 H1D 109.0 . . ?
H1C C1 H1D 107.8 . . ?
O4 B2 O5 110.70(18) . 3_654 ?
O4 B2 O1 114.81(19) . . ?
O5 B2 O1 108.51(16) 3_654 . ?
O4 B2 O3 105.13(16) . 6_565 ?
O5 B2 O3 109.59(18) 3_654 6_565 ?
O1 B2 O3 107.95(16) . 6_565 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.052
_database_code_depnum_ccdc_archive 'CCDC 955550'
