# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 N2 O4 P Zn'
_chemical_formula_weight         372.63

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'
P P 0.1023 0.0942 '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   C2/c

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                   33.174(7)
_cell_length_b                   5.5878(11)
_cell_length_c                   20.516(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 127.93(3)
_cell_angle_gamma                90.00
_cell_volume                     2999.6(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3423
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      27.45

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1528
_exptl_absorpt_coefficient_mu    1.763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.776
_exptl_absorpt_correction_T_max  0.868
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         image
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13309
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av__unetI/netI    0.0503
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         27.45
_reflns_number_total             3423
_reflns_number_gt                2439
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXL-97
_computing_publication_material  SHELXL-97

_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. 

 
Restraints on bond lengths and atomic displacement paremeters were applied 
by using DFIX and DELU command in SHELX program.

The used restraints are:

DELU 0.02 c1 C6 c4 c3 c5 c6
DELU 0.002  c1 C2
isor 0.005  c1 C2
isor 0.005  c1 C6
isor 0.005  c3 C4
isor 0.005  c5 C4
dfix 1.4 0.002 c1 c6
dfix 1.4 0.002 c3 c4
dfix 1.4 0.002 c4 c5 

;

_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)+(0.0359P)²+38.1668P] 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         3423
_refine_ls_number_parameters     199
_refine_ls_number_restraints     59
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1562
_refine_ls_wR_factor_gt          0.1083
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      1.191
_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
Zn Zn 0.11928(2) 0.35377(11) 0.09689(4) 0.02479(19) Uani 1 1 d . . .
O1 O 0.05371(15) 0.2939(8) 0.0713(3) 0.0365(10) Uani 1 1 d . . .
N2 N 0.23171(18) 0.5492(9) 0.3410(3) 0.0320(11) Uani 1 1 d . . .
N1 N 0.17881(17) 0.3911(9) 0.2172(3) 0.0286(10) Uani 1 1 d . . .
C11 C 0.2195(2) 0.2394(11) 0.2658(3) 0.0306(12) Uani 1 1 d . . .
H11A H 0.2238 0.0937 0.2490 0.037 Uiso 1 1 calc R . .
C9 C 0.0422(2) 0.4306(10) 0.1071(3) 0.0288(12) Uani 1 1 d . . .
C10 C 0.1872(2) 0.5760(10) 0.2641(3) 0.0306(12) Uani 1 1 d . . .
H10A H 0.1655 0.7069 0.2466 0.037 Uiso 1 1 calc R . .
C12 C 0.2524(2) 0.3358(12) 0.3425(4) 0.0356(13) Uani 1 1 d . . .
H12A H 0.2831 0.2697 0.3872 0.043 Uiso 1 1 calc R . .
C14 C 0.2391(3) 0.6593(12) 0.4651(3) 0.0401(15) Uani 1 1 d . . .
H14A H 0.2519 0.5012 0.4885 0.048 Uiso 1 1 calc R . .
H14B H 0.2022 0.6559 0.4325 0.048 Uiso 1 1 calc R . .
C13 C 0.2531(3) 0.7178(13) 0.4096(4) 0.0414(16) Uani 1 1 d . . .
H13A H 0.2410 0.8776 0.3873 0.050 Uiso 1 1 calc R . .
H13B H 0.2900 0.7181 0.4422 0.050 Uiso 1 1 calc R . .
O2 O 0.06771(17) 0.6062(8) 0.1491(3) 0.0449(11) Uani 1 1 d . . .
P P -0.10226(5) 0.1523(2) -0.00265(8) 0.0232(3) Uani 1 1 d . . .
C7 C -0.0368(2) 0.1605(10) 0.0360(3) 0.0284(11) Uani 1 1 d . . .
H7A H -0.0204 0.0113 0.0644 0.034 Uiso 1 1 calc R . .
H7B H -0.0360 0.1729 -0.0103 0.034 Uiso 1 1 calc R . .
C8 C -0.0065(2) 0.3688(10) 0.0953(3) 0.0287(12) Uani 1 1 d . . .
H8A H -0.0283 0.5092 0.0747 0.034 Uiso 1 1 calc R . .
H8B H 0.0023 0.3293 0.1487 0.034 Uiso 1 1 calc R . .
C1 C -0.1018(2) 0.1052(10) 0.0846(3) 0.0304(11) Uani 1 1 d DU . .
C6 C -0.1233(3) 0.2713(14) 0.1060(5) 0.064(2) Uani 1 1 d DU . .
H6A H -0.1386 0.4086 0.0742 0.076 Uiso 1 1 calc R . .
C4 C -0.0999(3) 0.0323(11) 0.2224(4) 0.0486(17) Uani 1 1 d DU . .
H4A H -0.0992 0.0094 0.2680 0.058 Uiso 1 1 calc R . .
C2 C -0.0806(4) -0.0935(17) 0.1325(6) 0.076(2) Uani 1 1 d U . .
H2A H -0.0666 -0.2078 0.1186 0.091 Uiso 1 1 calc R . .
C5 C -0.1222(4) 0.2355(14) 0.1725(5) 0.079(3) Uani 1 1 d DU . .
H5A H -0.1367 0.3498 0.1853 0.095 Uiso 1 1 calc R . .
O4 O -0.12693(14) 0.3936(7) -0.0393(2) 0.0294(9) Uani 1 1 d . . .
C3 C -0.0786(4) -0.1347(16) 0.2006(6) 0.084(3) Uani 1 1 d DU . .
H3A H -0.0633 -0.2728 0.2319 0.100 Uiso 1 1 calc R . .
O3 O -0.13094(15) -0.0533(7) -0.0615(2) 0.0311(9) 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
Zn 0.0245(3) 0.0264(3) 0.0237(3) -0.0021(3) 0.0150(3) -0.0018(3)
O1 0.030(2) 0.043(2) 0.045(2) -0.017(2) 0.027(2) -0.0095(19)
N2 0.031(2) 0.038(3) 0.024(2) -0.007(2) 0.015(2) -0.009(2)
N1 0.027(2) 0.034(3) 0.025(2) -0.005(2) 0.017(2) -0.002(2)
C11 0.031(3) 0.029(3) 0.032(3) 0.006(2) 0.020(3) 0.006(2)
C9 0.026(3) 0.031(3) 0.025(2) 0.000(2) 0.014(2) 0.000(2)
C10 0.037(3) 0.027(3) 0.027(3) 0.001(2) 0.019(2) 0.004(2)
C12 0.030(3) 0.041(3) 0.029(3) 0.005(3) 0.015(2) 0.003(3)
C14 0.045(4) 0.046(4) 0.026(3) -0.009(3) 0.020(3) -0.013(3)
C13 0.048(4) 0.047(4) 0.028(3) -0.014(3) 0.023(3) -0.019(3)
O2 0.042(3) 0.044(3) 0.050(3) -0.017(2) 0.029(2) -0.015(2)
P 0.0232(7) 0.0232(7) 0.0261(6) -0.0007(6) 0.0166(6) -0.0002(6)
C7 0.024(3) 0.030(3) 0.032(3) -0.006(2) 0.018(2) -0.004(2)
C8 0.027(3) 0.029(3) 0.032(3) -0.003(2) 0.019(2) 0.000(2)
C1 0.029(2) 0.035(2) 0.031(2) -0.0037(18) 0.0205(19) -0.0034(19)
C6 0.079(4) 0.071(4) 0.057(3) 0.010(3) 0.050(3) 0.027(3)
C4 0.055(3) 0.053(3) 0.044(3) 0.001(2) 0.034(2) -0.003(2)
C2 0.111(5) 0.063(4) 0.075(4) 0.026(3) 0.067(4) 0.031(3)
C5 0.099(5) 0.094(5) 0.071(4) 0.004(3) 0.066(4) 0.028(4)
O4 0.028(2) 0.030(2) 0.033(2) 0.0034(17) 0.0201(17) 0.0028(17)
C3 0.110(5) 0.084(5) 0.074(4) 0.019(4) 0.065(4) 0.018(4)
O3 0.030(2) 0.028(2) 0.037(2) -0.0060(18) 0.0213(18) -0.0010(17)

_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
Zn O1 1.927(4) . ?
Zn O4 1.955(4) 5_565 ?
Zn O3 1.960(4) 5 ?
Zn N1 2.010(5) . ?
O1 C9 1.271(7) . ?
N2 C10 1.353(7) . ?
N2 C12 1.368(8) . ?
N2 C13 1.463(7) . ?
N1 C10 1.320(7) . ?
N1 C11 1.371(7) . ?
C11 C12 1.359(8) . ?
C11 H11A 0.9300 . ?
C9 O2 1.236(7) . ?
C9 C8 1.520(8) . ?
C10 H10A 0.9300 . ?
C12 H12A 0.9300 . ?
C14 C13 1.506(8) . ?
C14 C14 1.527(11) 7_566 ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
P O3 1.507(4) . ?
P O4 1.516(4) . ?
P C7 1.797(5) . ?
P C1 1.798(5) . ?
C7 C8 1.530(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C1 C2 1.358(10) . ?
C1 C6 1.396(2) . ?
C6 C5 1.357(10) . ?
C6 H6A 0.9300 . ?
C4 C5 1.397(2) . ?
C4 C3 1.397(2) . ?
C4 H4A 0.9300 . ?
C2 C3 1.378(11) . ?
C2 H2A 0.9300 . ?
C5 H5A 0.9300 . ?
O4 Zn 1.955(4) 5_565 ?
C3 H3A 0.9300 . ?
O3 Zn 1.960(4) 5 ?

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 Zn O4 120.32(18) . 5_565 ?
O1 Zn O3 101.38(17) . 5 ?
O4 Zn O3 105.40(16) 5_565 5 ?
O1 Zn N1 116.43(18) . . ?
O4 Zn N1 105.81(18) 5_565 . ?
O3 Zn N1 105.96(18) 5 . ?
C9 O1 Zn 115.4(4) . . ?
C10 N2 C12 107.2(5) . . ?
C10 N2 C13 125.9(5) . . ?
C12 N2 C13 126.9(5) . . ?
C10 N1 C11 106.3(5) . . ?
C10 N1 Zn 125.7(4) . . ?
C11 N1 Zn 127.9(4) . . ?
C12 C11 N1 109.2(5) . . ?
C12 C11 H11A 125.4 . . ?
N1 C11 H11A 125.4 . . ?
O2 C9 O1 124.0(5) . . ?
O2 C9 C8 119.8(5) . . ?
O1 C9 C8 116.1(5) . . ?
N1 C10 N2 110.7(5) . . ?
N1 C10 H10A 124.6 . . ?
N2 C10 H10A 124.6 . . ?
C11 C12 N2 106.5(5) . . ?
C11 C12 H12A 126.7 . . ?
N2 C12 H12A 126.7 . . ?
C13 C14 C14 112.2(7) . 7_566 ?
C13 C14 H14A 109.2 . . ?
C14 C14 H14A 109.2 7_566 . ?
C13 C14 H14B 109.2 . . ?
C14 C14 H14B 109.2 7_566 . ?
H14A C14 H14B 107.9 . . ?
N2 C13 C14 113.2(5) . . ?
N2 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
N2 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.8 . . ?
O3 P O4 113.5(2) . . ?
O3 P C7 111.7(2) . . ?
O4 P C7 109.5(2) . . ?
O3 P C1 107.5(2) . . ?
O4 P C1 107.2(2) . . ?
C7 P C1 107.2(3) . . ?
C8 C7 P 113.2(4) . . ?
C8 C7 H7A 108.9 . . ?
P C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
P C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C7 114.4(5) . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C2 C1 C6 116.9(6) . . ?
C2 C1 P 121.7(5) . . ?
C6 C1 P 121.5(5) . . ?
C5 C6 C1 121.0(7) . . ?
C5 C6 H6A 119.5 . . ?
C1 C6 H6A 119.5 . . ?
C5 C4 C3 116.9(7) . . ?
C5 C4 H4A 121.6 . . ?
C3 C4 H4A 121.6 . . ?
C1 C2 C3 123.5(8) . . ?
C1 C2 H2A 118.2 . . ?
C3 C2 H2A 118.2 . . ?
C6 C5 C4 122.1(7) . . ?
C6 C5 H5A 119.0 . . ?
C4 C5 H5A 119.0 . . ?
P O4 Zn 135.3(2) . 5_565 ?
C2 C3 C4 119.6(8) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 H3A 120.2 . . ?
P O3 Zn 141.1(3) . 5 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.185
_refine_diff_density_min         -1.105
_refine_diff_density_rms         0.186
_database_code_depnum_ccdc_archive 'CCDC 969993'
#######################################################################
#
#                 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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 N2 O4 P Zn'
_chemical_formula_weight         372.63

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'
P P 0.1023 0.0942 '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                   11.496(2)
_cell_length_b                   13.665(3)
_cell_length_c                   11.051(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.53(3)
_cell_angle_gamma                90.00
_cell_volume                     1553.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3544
_cell_measurement_theta_min      3.58
_cell_measurement_theta_max      27.480

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             764
_exptl_absorpt_coefficient_mu    1.702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.486
_exptl_absorpt_correction_T_max  0.665
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         image
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14919
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.58
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3544
_reflns_number_gt                3079
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXL-97
_computing_publication_material  SHELXL-97

_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)+(0.0436P)²+10.4208P] 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         3544
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1681
_refine_ls_wR_factor_gt          0.1640
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_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
Zn Zn 0.03492(6) 0.23958(4) 0.10306(6) 0.02773(19) Uani 1 1 d . . .
C1 C -0.3667(5) -0.1923(4) 0.0107(6) 0.0317(11) Uani 1 1 d . . .
C2 C -0.4168(6) -0.1800(5) 0.1033(7) 0.0466(15) Uani 1 1 d . . .
H2A H -0.3607 -0.1771 0.1953 0.056 Uiso 1 1 calc R . .
C3 C -0.5478(7) -0.1719(6) 0.0604(9) 0.062(2) Uani 1 1 d . . .
H3A H -0.5804 -0.1616 0.1227 0.074 Uiso 1 1 calc R . .
C4 C -0.6319(7) -0.1792(6) -0.0757(9) 0.065(2) Uani 1 1 d . . .
H4A H -0.7211 -0.1754 -0.1044 0.078 Uiso 1 1 calc R . .
C5 C -0.5856(7) -0.1916(7) -0.1675(9) 0.068(2) Uani 1 1 d . . .
H5A H -0.6429 -0.1962 -0.2590 0.082 Uiso 1 1 calc R . .
C6 C -0.4520(6) -0.1975(6) -0.1253(7) 0.0545(18) Uani 1 1 d . . .
H6A H -0.4202 -0.2049 -0.1887 0.065 Uiso 1 1 calc R . .
C7 C -0.1397(5) -0.0714(4) 0.0906(5) 0.0336(11) Uani 1 1 d . . .
H7A H -0.1631 -0.0408 0.1558 0.040 Uiso 1 1 calc R . .
H7B H -0.0456 -0.0704 0.1282 0.040 Uiso 1 1 calc R . .
C8 C -0.1960(6) -0.0105(4) -0.0388(6) 0.0356(12) Uani 1 1 d . . .
H8A H -0.1864 -0.0471 -0.1091 0.043 Uiso 1 1 calc R . .
H8B H -0.2884 -0.0018 -0.0675 0.043 Uiso 1 1 calc R . .
C9 C -0.1351(5) 0.0888(4) -0.0273(6) 0.0337(11) Uani 1 1 d . . .
C10 C -0.1539(5) 0.3922(4) 0.0884(6) 0.0377(12) Uani 1 1 d . . .
H10A H -0.1549 0.3692 0.1671 0.045 Uiso 1 1 calc R . .
C11 C -0.1093(6) 0.4094(5) -0.0798(7) 0.0488(16) Uani 1 1 d . . .
H11A H -0.0732 0.4001 -0.1394 0.059 Uiso 1 1 calc R . .
C12 C -0.1972(7) 0.4788(6) -0.0914(8) 0.0584(19) Uani 1 1 d . . .
H12A H -0.2322 0.5257 -0.1593 0.070 Uiso 1 1 calc R . .
C13 C -0.3201(7) 0.5223(6) 0.0430(10) 0.065(2) Uani 1 1 d . . .
H13A H -0.3294 0.5874 0.0049 0.078 Uiso 1 1 calc R . .
H13B H -0.2883 0.5290 0.1400 0.078 Uiso 1 1 calc R . .
C14 C -0.4516(6) 0.4728(6) -0.0158(8) 0.0563(18) Uani 1 1 d . . .
H14A H -0.4847 0.4681 -0.1132 0.068 Uiso 1 1 calc R . .
H14B H -0.4418 0.4069 0.0200 0.068 Uiso 1 1 calc R . .
N1 N -0.0816(4) 0.3549(3) 0.0338(5) 0.0330(10) Uani 1 1 d . . .
N2 N -0.2246(5) 0.4669(4) 0.0154(6) 0.0446(12) Uani 1 1 d . . .
O1 O -0.0493(4) 0.1141(3) 0.0900(4) 0.0409(9) Uani 1 1 d . . .
O2 O -0.1703(5) 0.1397(3) -0.1304(5) 0.0505(11) Uani 1 1 d . . .
O3 O -0.1695(4) -0.2434(3) -0.0422(4) 0.0352(9) Uani 1 1 d . . .
O4 O -0.1321(4) -0.2483(3) 0.2015(4) 0.0446(10) Uani 1 1 d . . .
P P -0.19281(13) -0.19638(10) 0.06874(13) 0.0275(3) 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
Zn 0.0255(3) 0.0260(3) 0.0315(3) -0.0009(2) 0.0126(2) 0.0007(2)
C1 0.032(3) 0.025(2) 0.040(3) -0.001(2) 0.018(2) 0.000(2)
C2 0.046(4) 0.054(4) 0.050(4) 0.004(3) 0.031(3) 0.004(3)
C3 0.048(4) 0.074(5) 0.080(5) 0.015(4) 0.044(4) 0.013(4)
C4 0.036(4) 0.064(5) 0.097(6) 0.000(4) 0.032(4) 0.007(3)
C5 0.034(3) 0.082(6) 0.072(5) -0.018(4) 0.010(3) 0.008(4)
C6 0.036(3) 0.079(5) 0.045(4) -0.014(3) 0.016(3) 0.006(3)
C7 0.034(3) 0.034(3) 0.032(3) -0.006(2) 0.015(2) -0.009(2)
C8 0.036(3) 0.027(3) 0.039(3) -0.004(2) 0.012(2) -0.003(2)
C9 0.034(3) 0.029(3) 0.044(3) -0.002(2) 0.023(2) -0.001(2)
C10 0.032(3) 0.041(3) 0.039(3) -0.001(2) 0.015(2) 0.005(2)
C11 0.043(3) 0.061(4) 0.048(4) 0.018(3) 0.025(3) 0.014(3)
C12 0.053(4) 0.055(4) 0.067(5) 0.025(4) 0.028(4) 0.021(3)
C13 0.042(4) 0.055(4) 0.096(6) -0.020(4) 0.029(4) 0.009(3)
C14 0.040(4) 0.052(4) 0.077(5) -0.012(4) 0.026(3) 0.009(3)
N1 0.031(2) 0.032(2) 0.037(2) 0.0014(19) 0.0162(19) 0.0044(18)
N2 0.032(3) 0.039(3) 0.061(3) -0.005(2) 0.019(2) 0.007(2)
O1 0.040(2) 0.0270(19) 0.049(2) -0.0001(17) 0.0131(19) -0.0081(16)
O2 0.063(3) 0.042(2) 0.048(3) 0.007(2) 0.026(2) -0.003(2)
O3 0.0318(19) 0.041(2) 0.038(2) -0.0069(17) 0.0206(17) -0.0043(16)
O4 0.050(3) 0.045(2) 0.034(2) 0.0077(18) 0.0142(19) -0.003(2)
P 0.0270(6) 0.0302(7) 0.0268(6) -0.0007(5) 0.0132(5) -0.0024(5)

_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
Zn O1 1.942(4) . ?
Zn O3 1.943(4) 3 ?
Zn O4 1.946(4) 2 ?
Zn N1 1.987(5) . ?
C1 C6 1.382(9) . ?
C1 C2 1.391(8) . ?
C1 P 1.807(5) . ?
C2 C3 1.367(9) . ?
C2 H2A 0.9300 . ?
C3 C4 1.381(12) . ?
C3 H3A 0.9300 . ?
C4 C5 1.350(12) . ?
C4 H4A 0.9300 . ?
C5 C6 1.395(9) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.526(8) . ?
C7 P 1.793(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.507(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O2 1.238(7) . ?
C9 O1 1.277(7) . ?
C10 N1 1.327(7) . ?
C10 N2 1.329(8) . ?
C10 H10A 0.9300 . ?
C11 C12 1.350(9) . ?
C11 N1 1.369(8) . ?
C11 H11A 0.9300 . ?
C12 N2 1.361(9) . ?
C12 H12A 0.9300 . ?
C13 N2 1.474(8) . ?
C13 C14 1.513(10) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C14 1.503(12) 3_465 ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
O3 P 1.511(4) . ?
O3 Zn 1.943(4) 3 ?
O4 P 1.493(4) . ?
O4 Zn 1.946(4) 2_545 ?

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 Zn O3 116.46(18) . 3 ?
O1 Zn O4 100.24(19) . 2 ?
O3 Zn O4 103.32(19) 3 2 ?
O1 Zn N1 116.33(19) . . ?
O3 Zn N1 110.44(18) 3 . ?
O4 Zn N1 108.32(19) 2 . ?
C6 C1 C2 118.7(6) . . ?
C6 C1 P 121.3(5) . . ?
C2 C1 P 119.9(5) . . ?
C3 C2 C1 120.6(7) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
C2 C3 C4 119.9(7) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C5 C4 C3 120.6(7) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 120.0(8) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C1 C6 C5 120.1(7) . . ?
C1 C6 H6A 119.9 . . ?
C5 C6 H6A 119.9 . . ?
C8 C7 P 114.6(4) . . ?
C8 C7 H7A 108.6 . . ?
P C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
P C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C7 115.2(5) . . ?
C9 C8 H8A 108.5 . . ?
C7 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
C7 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
O2 C9 O1 124.7(5) . . ?
O2 C9 C8 118.6(5) . . ?
O1 C9 C8 116.7(5) . . ?
N1 C10 N2 110.8(5) . . ?
N1 C10 H10A 124.6 . . ?
N2 C10 H10A 124.6 . . ?
C12 C11 N1 109.1(6) . . ?
C12 C11 H11A 125.5 . . ?
N1 C11 H11A 125.5 . . ?
C11 C12 N2 106.7(6) . . ?
C11 C12 H12A 126.7 . . ?
N2 C12 H12A 126.7 . . ?
N2 C13 C14 112.1(6) . . ?
N2 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
N2 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C14 C14 C13 112.3(8) 3_465 . ?
C14 C14 H14A 109.1 3_465 . ?
C13 C14 H14A 109.1 . . ?
C14 C14 H14B 109.1 3_465 . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
C10 N1 C11 105.8(5) . . ?
C10 N1 Zn 125.5(4) . . ?
C11 N1 Zn 128.7(4) . . ?
C10 N2 C12 107.6(5) . . ?
C10 N2 C13 125.4(6) . . ?
C12 N2 C13 126.9(6) . . ?
C9 O1 Zn 116.6(4) . . ?
P O3 Zn 136.6(2) . 3 ?
P O4 Zn 156.3(3) . 2_545 ?
O4 P O3 114.9(3) . . ?
O4 P C7 109.8(3) . . ?
O3 P C7 110.0(2) . . ?
O4 P C1 108.7(3) . . ?
O3 P C1 107.1(2) . . ?
C7 P C1 105.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.509
_refine_diff_density_min         -0.742
_refine_diff_density_rms         0.139
_exptl_crystal_preparation       Luminescent
_database_code_depnum_ccdc_archive 'CCDC 969994'
