# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry B.
# 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.
#
#  This CIF is provided on the understanding that it is used for bona
#  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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_bw

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H25 Cl N4 O3 Zn, F6 P, C2 H3 N'
_chemical_formula_sum            'C29 H28 Cl F6 N5 O3 P Zn'
_chemical_formula_weight         740.35

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

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

_cell_length_a                   17.9746(13)
_cell_length_b                   8.2125(6)
_cell_length_c                   21.4102(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.6920(10)
_cell_angle_gamma                90.00
_cell_volume                     3159.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9919
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1508
_exptl_absorpt_coefficient_mu    0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7218
_exptl_absorpt_correction_T_max  0.8097
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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 scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25157
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.46
_diffrn_reflns_theta_max         27.30
_reflns_number_total             6960
_reflns_number_gt                6166
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_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 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. 

Hydrogen atoms bound to a water molecule were constrained by DFIX and DANG.
;

_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)+(0.0664P)²+1.3385P] 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         6960
_refine_ls_number_parameters     425
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.1147
_refine_ls_wR_factor_gt          0.1082
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.001

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 0.268337(13) 0.38129(3) 0.141165(10) 0.01657(9) Uani 1 1 d . . .
Cl1 Cl 0.19506(3) 0.48692(6) 0.21771(2) 0.02235(12) Uani 1 1 d . . .
P1 P 0.60690(3) 0.18162(7) 0.10098(2) 0.02335(13) Uani 1 1 d . . .
F1 F 0.55836(9) 0.10287(17) 0.04502(6) 0.0363(3) Uani 1 1 d . . .
F2 F 0.57330(9) 0.35810(16) 0.08390(7) 0.0351(3) Uani 1 1 d . . .
F3 F 0.67349(8) 0.21387(18) 0.05388(7) 0.0371(3) Uani 1 1 d . . .
F4 F 0.64072(10) 0.00636(17) 0.11750(7) 0.0442(4) Uani 1 1 d . . .
F5 F 0.54069(9) 0.15016(19) 0.14772(7) 0.0386(4) Uani 1 1 d . . .
F6 F 0.65573(8) 0.26158(18) 0.15686(6) 0.0382(3) Uani 1 1 d . . .
O1 O -0.05540(8) 0.30837(18) 0.05318(7) 0.0230(3) Uani 1 1 d . . .
O2 O 0.16612(8) 0.46716(16) 0.07345(6) 0.0202(3) Uani 1 1 d . . .
O3 O 0.35625(9) 0.26583(18) 0.19384(7) 0.0233(3) Uani 1 1 d D . .
N1 N 0.03077(10) 0.4455(2) 0.11114(8) 0.0238(4) Uani 1 1 d . . .
N2 N 0.31646(10) 0.3150(2) 0.04903(8) 0.0182(3) Uani 1 1 d . . .
N3 N 0.22118(10) 0.1509(2) 0.12544(8) 0.0184(3) Uani 1 1 d . . .
N4 N 0.33930(10) 0.5767(2) 0.12600(8) 0.0176(3) Uani 1 1 d . . .
N5 N 0.47694(12) 0.4782(3) 0.22759(10) 0.0352(5) Uani 1 1 d . . .
C1 C -0.03737(12) 0.4558(3) 0.14076(10) 0.0228(4) Uani 1 1 d . . .
C2 C -0.05687(13) 0.5311(3) 0.19629(10) 0.0277(5) Uani 1 1 d . . .
H2 H -0.0221 0.5873 0.2211 0.033 Uiso 1 1 calc R . .
C3 C -0.13096(14) 0.5180(3) 0.21282(11) 0.0297(5) Uani 1 1 d . . .
H3 H -0.1462 0.5668 0.2495 0.036 Uiso 1 1 calc R . .
C4 C -0.18310(13) 0.4328(3) 0.17542(11) 0.0294(5) Uani 1 1 d . . .
H4 H -0.2321 0.4269 0.1880 0.035 Uiso 1 1 calc R . .
C5 C -0.16392(13) 0.3568(3) 0.12021(11) 0.0275(5) Uani 1 1 d . . .
H5 H -0.1983 0.2998 0.0954 0.033 Uiso 1 1 calc R . .
C6 C -0.09017(13) 0.3721(2) 0.10474(10) 0.0236(4) Uani 1 1 d . . .
C7 C 0.01733(12) 0.3585(2) 0.06141(10) 0.0223(4) Uani 1 1 d . . .
C8 C 0.07179(12) 0.3116(2) 0.01602(9) 0.0213(4) Uani 1 1 d . . .
C9 C 0.05425(13) 0.2093(2) -0.03492(10) 0.0244(4) Uani 1 1 d . . .
H9 H 0.0059 0.1702 -0.0404 0.029 Uiso 1 1 calc R . .
C10 C 0.10765(13) 0.1656(3) -0.07706(10) 0.0244(4) Uani 1 1 d . . .
C11 C 0.08890(15) 0.0599(3) -0.13305(11) 0.0318(5) Uani 1 1 d . . .
H11A H 0.0776 0.1277 -0.1686 0.048 Uiso 1 1 calc R . .
H11B H 0.0466 -0.0067 -0.1244 0.048 Uiso 1 1 calc R . .
H11C H 0.1307 -0.0084 -0.1418 0.048 Uiso 1 1 calc R . .
C12 C 0.17999(12) 0.2248(2) -0.06740(9) 0.0227(4) Uani 1 1 d . . .
H12 H 0.2162 0.1958 -0.0955 0.027 Uiso 1 1 calc R . .
C13 C 0.19982(12) 0.3254(2) -0.01735(9) 0.0200(4) Uani 1 1 d . . .
C14 C 0.14497(12) 0.3696(2) 0.02440(9) 0.0189(4) Uani 1 1 d . . .
C15 C 0.27782(12) 0.3874(2) -0.00731(9) 0.0208(4) Uani 1 1 d . . .
H15A H 0.3063 0.3627 -0.0439 0.025 Uiso 1 1 calc R . .
H15B H 0.2764 0.5049 -0.0027 0.025 Uiso 1 1 calc R . .
C16 C 0.31581(12) 0.1356(2) 0.04665(10) 0.0206(4) Uani 1 1 d . . .
H16A H 0.3601 0.0937 0.0681 0.025 Uiso 1 1 calc R . .
H16B H 0.3167 0.1001 0.0035 0.025 Uiso 1 1 calc R . .
C17 C 0.39230(12) 0.3828(2) 0.05423(10) 0.0217(4) Uani 1 1 d . . .
H17A H 0.4130 0.3901 0.0130 0.026 Uiso 1 1 calc R . .
H17B H 0.4237 0.3106 0.0793 0.026 Uiso 1 1 calc R . .
C18 C 0.24731(11) 0.0673(2) 0.07688(9) 0.0193(4) Uani 1 1 d . . .
C19 C 0.21472(13) -0.0781(3) 0.05695(10) 0.0253(4) Uani 1 1 d . . .
H19 H 0.2333 -0.1342 0.0231 0.030 Uiso 1 1 calc R . .
C20 C 0.15430(13) -0.1378(2) 0.08821(11) 0.0259(5) Uani 1 1 d . . .
H20 H 0.1312 -0.2337 0.0751 0.031 Uiso 1 1 calc R . .
C21 C 0.12843(13) -0.0534(3) 0.13927(10) 0.0253(4) Uani 1 1 d . . .
H21 H 0.0888 -0.0932 0.1616 0.030 Uiso 1 1 calc R . .
C22 C 0.16285(12) 0.0912(2) 0.15621(10) 0.0221(4) Uani 1 1 d . . .
H22 H 0.1451 0.1492 0.1900 0.027 Uiso 1 1 calc R . .
C23 C 0.39193(11) 0.5498(2) 0.08380(9) 0.0191(4) Uani 1 1 d . . .
C24 C 0.44467(12) 0.6662(3) 0.07048(10) 0.0229(4) Uani 1 1 d . . .
H24 H 0.4791 0.6471 0.0397 0.027 Uiso 1 1 calc R . .
C25 C 0.44570(12) 0.8115(3) 0.10340(10) 0.0245(4) Uani 1 1 d . . .
H25 H 0.4810 0.8909 0.0952 0.029 Uiso 1 1 calc R . .
C26 C 0.39371(12) 0.8371(2) 0.14849(10) 0.0219(4) Uani 1 1 d . . .
H26 H 0.3944 0.9320 0.1722 0.026 Uiso 1 1 calc R . .
C27 C 0.34017(11) 0.7178(2) 0.15778(9) 0.0197(4) Uani 1 1 d . . .
H27 H 0.3038 0.7364 0.1869 0.024 Uiso 1 1 calc R . .
C28 C 0.52857(14) 0.5493(3) 0.21489(10) 0.0292(5) Uani 1 1 d . . .
C29 C 0.59582(15) 0.6377(3) 0.19897(13) 0.0376(6) Uani 1 1 d . . .
H29A H 0.6308 0.6343 0.2337 0.056 Uiso 1 1 calc R . .
H29B H 0.5834 0.7489 0.1895 0.056 Uiso 1 1 calc R . .
H29C H 0.6175 0.5880 0.1632 0.056 Uiso 1 1 calc R . .
H3A H 0.3436(16) 0.202(3) 0.2222(12) 0.050(9) Uiso 1 1 d D . .
H3B H 0.3877(14) 0.332(3) 0.2088(13) 0.045(9) Uiso 1 1 d D . .


_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 N4 2.0816(17) . ?
Zn1 N3 2.0967(17) . ?
Zn1 O3 2.1361(15) . ?
Zn1 N2 2.2441(16) . ?
Zn1 Cl1 2.3023(5) . ?
Zn1 O2 2.4121(15) . ?
P1 F1 1.5979(15) . ?
P1 F4 1.5980(15) . ?
P1 F5 1.5984(15) . ?
P1 F6 1.6034(14) . ?
P1 F2 1.6081(15) . ?
P1 F3 1.6095(14) . ?
O1 C7 1.377(3) . ?
O1 C6 1.387(3) . ?
O2 C14 1.366(2) . ?
N1 C7 1.299(3) . ?
N1 C1 1.398(3) . ?
N2 C17 1.474(3) . ?
N2 C16 1.475(2) . ?
N2 C15 1.497(3) . ?
N3 C18 1.342(3) . ?
N3 C22 1.347(3) . ?
N4 C27 1.344(3) . ?
N4 C23 1.346(2) . ?
N5 C28 1.136(3) . ?
C1 C6 1.388(3) . ?
C1 C2 1.394(3) . ?
C2 C3 1.392(3) . ?
C3 C4 1.402(3) . ?
C4 C5 1.389(3) . ?
C5 C6 1.382(3) . ?
C7 C8 1.452(3) . ?
C8 C9 1.405(3) . ?
C8 C14 1.406(3) . ?
C9 C10 1.384(3) . ?
C10 C12 1.398(3) . ?
C10 C11 1.510(3) . ?
C12 C13 1.391(3) . ?
C13 C14 1.398(3) . ?
C13 C15 1.501(3) . ?
C16 C18 1.515(3) . ?
C17 C23 1.510(3) . ?
C18 C19 1.391(3) . ?
C19 C20 1.382(3) . ?
C20 C21 1.386(3) . ?
C21 C22 1.382(3) . ?
C23 C24 1.382(3) . ?
C24 C25 1.386(3) . ?
C25 C26 1.379(3) . ?
C26 C27 1.391(3) . ?
C28 C29 1.459(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
N4 Zn1 N3 156.57(7) . . ?
N4 Zn1 O3 88.71(6) . . ?
N3 Zn1 O3 88.48(6) . . ?
N4 Zn1 N2 78.23(6) . . ?
N3 Zn1 N2 78.72(6) . . ?
O3 Zn1 N2 93.33(6) . . ?
N4 Zn1 Cl1 100.76(5) . . ?
N3 Zn1 Cl1 102.55(5) . . ?
O3 Zn1 Cl1 102.78(4) . . ?
N2 Zn1 Cl1 163.85(5) . . ?
N4 Zn1 O2 98.06(6) . . ?
N3 Zn1 O2 82.54(6) . . ?
O3 Zn1 O2 170.28(5) . . ?
N2 Zn1 O2 81.32(6) . . ?
Cl1 Zn1 O2 82.88(4) . . ?
F1 P1 F4 89.84(9) . . ?
F1 P1 F5 90.22(8) . . ?
F4 P1 F5 90.08(9) . . ?
F1 P1 F6 179.64(8) . . ?
F4 P1 F6 90.42(9) . . ?
F5 P1 F6 90.02(8) . . ?
F1 P1 F2 90.07(8) . . ?
F4 P1 F2 179.55(10) . . ?
F5 P1 F2 90.37(9) . . ?
F6 P1 F2 89.67(8) . . ?
F1 P1 F3 89.80(8) . . ?
F4 P1 F3 90.10(9) . . ?
F5 P1 F3 179.82(10) . . ?
F6 P1 F3 89.95(8) . . ?
F2 P1 F3 89.46(8) . . ?
C7 O1 C6 103.52(16) . . ?
C14 O2 Zn1 118.71(12) . . ?
C7 N1 C1 105.13(18) . . ?
C17 N2 C16 112.75(16) . . ?
C17 N2 C15 108.47(16) . . ?
C16 N2 C15 111.47(16) . . ?
C17 N2 Zn1 102.80(12) . . ?
C16 N2 Zn1 105.66(12) . . ?
C15 N2 Zn1 115.48(12) . . ?
C18 N3 C22 119.21(18) . . ?
C18 N3 Zn1 115.90(13) . . ?
C22 N3 Zn1 124.53(14) . . ?
C27 N4 C23 118.94(17) . . ?
C27 N4 Zn1 125.73(13) . . ?
C23 N4 Zn1 115.10(13) . . ?
C6 C1 C2 120.6(2) . . ?
C6 C1 N1 108.16(18) . . ?
C2 C1 N1 131.2(2) . . ?
C3 C2 C1 116.7(2) . . ?
C2 C3 C4 121.5(2) . . ?
C5 C4 C3 122.1(2) . . ?
C6 C5 C4 115.3(2) . . ?
C5 C6 O1 127.9(2) . . ?
C5 C6 C1 123.8(2) . . ?
O1 C6 C1 108.21(19) . . ?
N1 C7 O1 114.98(19) . . ?
N1 C7 C8 125.6(2) . . ?
O1 C7 C8 119.44(18) . . ?
C9 C8 C14 119.30(19) . . ?
C9 C8 C7 122.5(2) . . ?
C14 C8 C7 118.15(18) . . ?
C10 C9 C8 121.1(2) . . ?
C9 C10 C12 118.27(19) . . ?
C9 C10 C11 121.6(2) . . ?
C12 C10 C11 120.1(2) . . ?
C13 C12 C10 122.4(2) . . ?
C12 C13 C14 118.5(2) . . ?
C12 C13 C15 121.93(18) . . ?
C14 C13 C15 119.57(18) . . ?
O2 C14 C13 117.29(19) . . ?
O2 C14 C8 122.35(18) . . ?
C13 C14 C8 120.35(18) . . ?
N2 C15 C13 112.93(16) . . ?
N2 C16 C18 111.14(16) . . ?
N2 C17 C23 111.06(16) . . ?
N3 C18 C19 121.51(19) . . ?
N3 C18 C16 116.69(18) . . ?
C19 C18 C16 121.76(18) . . ?
C20 C19 C18 119.1(2) . . ?
C19 C20 C21 119.4(2) . . ?
C22 C21 C20 118.6(2) . . ?
N3 C22 C21 122.22(19) . . ?
N4 C23 C24 121.67(18) . . ?
N4 C23 C17 116.28(17) . . ?
C24 C23 C17 121.99(18) . . ?
C23 C24 C25 119.32(19) . . ?
C26 C25 C24 119.18(19) . . ?
C25 C26 C27 118.61(19) . . ?
N4 C27 C26 122.17(18) . . ?
N5 C28 C29 178.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        27.30
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.086
_database_code_depnum_ccdc_archive 'CCDC 979643'
