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

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#
#                 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
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#  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 
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data_0228b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H11 N O8 P2 Zn2'
_chemical_formula_weight         465.88

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                   15.2874(18)
_cell_length_b                   8.1363(10)
_cell_length_c                   11.3600(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.136(2)
_cell_angle_gamma                90.00
_cell_volume                     1409.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1754
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      26.80

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    3.673
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.3770
_exptl_absorpt_correction_T_max  0.8463
_exptl_absorpt_process_details   sadabs

_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  'Smart Apex II CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7719
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.34
_diffrn_reflns_theta_max         26.50
_reflns_number_total             2895
_reflns_number_gt                2147
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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^)+(0.0699P)^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         2895
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.1160
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.001
_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 0.55592(3) 0.16370(7) 0.47788(5) 0.01479(17) Uani 1 1 d . . .
Zn2 Zn 0.60777(3) -0.16325(6) 0.73841(5) 0.01448(17) Uani 1 1 d . . .
P1 P 0.65744(8) -0.16775(15) 0.48708(10) 0.0128(3) Uani 1 1 d . . .
P2 P 0.59177(8) 0.25162(15) 0.22758(10) 0.0133(3) Uani 1 1 d . . .
N1 N 0.6916(2) 0.1530(5) 0.4267(3) 0.0134(8) Uani 1 1 d . . .
O5 O 0.5154(2) 0.2268(4) 0.3089(3) 0.0159(7) Uani 1 1 d . . .
O3 O 0.6740(2) -0.2516(4) 0.6073(3) 0.0148(7) Uani 1 1 d . . .
O4 O 0.6202(2) 0.4288(4) 0.2238(3) 0.0227(8) Uani 1 1 d . . .
O6 O 0.5690(2) 0.1799(4) 0.1066(3) 0.0189(7) Uani 1 1 d . . .
O1 O 0.56680(19) -0.0868(4) 0.4773(3) 0.0157(7) Uani 1 1 d . . .
O2 O 0.6699(2) -0.2824(4) 0.3853(3) 0.0195(8) Uani 1 1 d . . .
O8 O 1.1534(3) 0.2837(6) 0.3860(4) 0.0575(14) Uani 1 1 d . . .
H8C H 1.1535 0.3090 0.4587 0.086 Uiso 1 1 d R . .
O7 O 1.1164(3) 0.4629(7) 0.2485(5) 0.079(2) Uani 1 1 d . . .
C3 C 0.7397(3) 0.3078(6) 0.4630(4) 0.0193(11) Uani 1 1 d . . .
H3A H 0.7411 0.3169 0.5482 0.023 Uiso 1 1 d R . .
H3B H 0.7061 0.4003 0.4301 0.023 Uiso 1 1 d R . .
C4 C 0.8329(3) 0.3238(6) 0.4267(4) 0.0190(10) Uani 1 1 d . . .
C5 C 0.8510(3) 0.4195(7) 0.3301(5) 0.0258(12) Uani 1 1 d . . .
H5A H 0.8056 0.4728 0.2866 0.031 Uiso 1 1 d R . .
C6 C 0.9018(4) 0.2477(7) 0.4915(5) 0.0301(13) Uani 1 1 d . . .
H6B H 0.8905 0.1856 0.5575 0.036 Uiso 1 1 d R . .
C1 C 0.7345(3) 0.0047(6) 0.4829(4) 0.0157(10) Uani 1 1 d . . .
H1A H 0.7568 0.0315 0.5627 0.019 Uiso 1 1 d R . .
H1B H 0.7839 -0.0274 0.4389 0.019 Uiso 1 1 d R . .
C2 C 0.6814(3) 0.1310(5) 0.2952(4) 0.0131(9) Uani 1 1 d . . .
H2B H 0.6709 0.0157 0.2774 0.016 Uiso 1 1 d R . .
H2C H 0.7355 0.1625 0.2615 0.016 Uiso 1 1 d R . .
C7 C 0.9365(4) 0.4363(7) 0.2983(5) 0.0299(13) Uani 1 1 d . . .
H7A H 0.9481 0.5010 0.2337 0.036 Uiso 1 1 d R . .
C8 C 0.9872(3) 0.2624(7) 0.4599(5) 0.0302(13) Uani 1 1 d . . .
H8A H 1.0326 0.2093 0.5035 0.036 Uiso 1 1 d R . .
C9 C 1.0048(3) 0.3572(6) 0.3619(5) 0.0248(12) Uani 1 1 d . . .
C10 C 1.0957(4) 0.3777(8) 0.3256(6) 0.0367(15) 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 0.0143(3) 0.0161(3) 0.0141(3) -0.0001(2) 0.0022(2) 0.0002(2)
Zn2 0.0146(3) 0.0154(3) 0.0135(3) 0.0010(2) 0.0013(2) 0.0003(2)
P1 0.0115(6) 0.0147(6) 0.0125(6) -0.0001(5) 0.0019(5) 0.0017(5)
P2 0.0132(6) 0.0135(6) 0.0134(6) 0.0036(5) 0.0018(4) 0.0002(5)
N1 0.014(2) 0.015(2) 0.0116(19) 0.0020(15) 0.0029(15) 0.0010(16)
O5 0.0100(16) 0.0244(19) 0.0132(16) 0.0012(14) 0.0009(13) 0.0002(14)
O3 0.0140(16) 0.0190(18) 0.0117(16) -0.0005(14) 0.0045(12) 0.0027(14)
O4 0.026(2) 0.0132(18) 0.029(2) 0.0034(15) 0.0016(16) 0.0000(15)
O6 0.0227(19) 0.0209(18) 0.0133(17) 0.0000(14) 0.0030(14) -0.0017(15)
O1 0.0135(16) 0.0133(17) 0.0207(18) 0.0017(14) 0.0052(14) -0.0003(14)
O2 0.0175(18) 0.0245(19) 0.0162(17) -0.0056(15) -0.0007(14) 0.0064(15)
O8 0.026(2) 0.084(4) 0.063(3) 0.036(3) 0.008(2) 0.012(2)
O7 0.031(3) 0.111(5) 0.096(4) 0.067(4) 0.026(3) 0.009(3)
C3 0.017(3) 0.019(3) 0.022(3) -0.001(2) 0.002(2) 0.000(2)
C4 0.013(2) 0.021(3) 0.023(3) -0.001(2) 0.002(2) -0.001(2)
C5 0.021(3) 0.028(3) 0.028(3) 0.008(2) 0.002(2) 0.001(2)
C6 0.025(3) 0.035(3) 0.030(3) 0.014(3) 0.002(2) -0.007(3)
C1 0.011(2) 0.021(2) 0.015(2) 0.003(2) -0.0001(18) 0.006(2)
C2 0.013(2) 0.012(2) 0.014(2) 0.0021(18) 0.0015(18) 0.0021(18)
C7 0.028(3) 0.031(3) 0.032(3) 0.010(2) 0.007(2) -0.001(2)
C8 0.016(3) 0.037(3) 0.038(3) 0.010(3) 0.000(2) -0.001(2)
C9 0.013(2) 0.026(3) 0.035(3) 0.004(2) 0.004(2) 0.000(2)
C10 0.025(3) 0.041(4) 0.044(4) 0.007(3) 0.006(3) -0.002(3)

_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 O6 1.938(3) 4_566 ?
Zn1 O5 2.040(3) . ?
Zn1 O1 2.045(3) . ?
Zn1 O1 2.076(3) 3_656 ?
Zn1 N1 2.195(4) . ?
Zn2 O2 1.911(3) 4_556 ?
Zn2 O4 1.926(3) 4_566 ?
Zn2 O5 1.988(3) 3_656 ?
Zn2 O3 1.994(3) . ?
P1 O2 1.509(3) . ?
P1 O1 1.531(3) . ?
P1 O3 1.531(3) . ?
P1 C1 1.835(5) . ?
P2 O4 1.507(4) . ?
P2 O6 1.510(3) . ?
P2 O5 1.554(3) . ?
P2 C2 1.811(4) . ?
N1 C1 1.494(6) . ?
N1 C3 1.501(6) . ?
N1 C2 1.502(5) . ?
O5 Zn2 1.988(3) 3_656 ?
O4 Zn2 1.926(3) 4_565 ?
O6 Zn1 1.938(3) 4_565 ?
O1 Zn1 2.076(3) 3_656 ?
O2 Zn2 1.911(3) 4 ?
O8 C10 1.322(7) . ?
O8 H8C 0.8500 . ?
O7 C10 1.178(7) . ?
C3 C4 1.517(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9699 . ?
C4 C6 1.387(7) . ?
C4 C5 1.389(7) . ?
C5 C7 1.388(7) . ?
C5 H5A 0.9300 . ?
C6 C8 1.384(7) . ?
C6 H6B 0.9300 . ?
C1 H1A 0.9699 . ?
C1 H1B 0.9700 . ?
C2 H2B 0.9700 . ?
C2 H2C 0.9699 . ?
C7 C9 1.385(7) . ?
C7 H7A 0.9300 . ?
C8 C9 1.396(7) . ?
C8 H8A 0.9299 . ?
C9 C10 1.488(8) . ?

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
O6 Zn1 O5 123.55(13) 4_566 . ?
O6 Zn1 O1 130.75(13) 4_566 . ?
O5 Zn1 O1 105.49(13) . . ?
O6 Zn1 O1 93.37(13) 4_566 3_656 ?
O5 Zn1 O1 95.03(12) . 3_656 ?
O1 Zn1 O1 77.01(13) . 3_656 ?
O6 Zn1 N1 100.25(14) 4_566 . ?
O5 Zn1 N1 89.41(13) . . ?
O1 Zn1 N1 83.17(13) . . ?
O1 Zn1 N1 160.17(13) 3_656 . ?
O2 Zn2 O4 104.99(15) 4_556 4_566 ?
O2 Zn2 O5 125.27(13) 4_556 3_656 ?
O4 Zn2 O5 109.36(14) 4_566 3_656 ?
O2 Zn2 O3 108.75(14) 4_556 . ?
O4 Zn2 O3 103.53(14) 4_566 . ?
O5 Zn2 O3 103.06(13) 3_656 . ?
O2 P1 O1 112.00(19) . . ?
O2 P1 O3 112.72(19) . . ?
O1 P1 O3 110.28(18) . . ?
O2 P1 C1 109.6(2) . . ?
O1 P1 C1 104.4(2) . . ?
O3 P1 C1 107.4(2) . . ?
O4 P2 O6 113.0(2) . . ?
O4 P2 O5 111.9(2) . . ?
O6 P2 O5 110.90(19) . . ?
O4 P2 C2 108.6(2) . . ?
O6 P2 C2 107.1(2) . . ?
O5 P2 C2 104.81(19) . . ?
C1 N1 C3 111.6(4) . . ?
C1 N1 C2 109.8(3) . . ?
C3 N1 C2 112.8(3) . . ?
C1 N1 Zn1 108.3(3) . . ?
C3 N1 Zn1 110.3(3) . . ?
C2 N1 Zn1 103.7(3) . . ?
P2 O5 Zn2 127.62(18) . 3_656 ?
P2 O5 Zn1 113.69(17) . . ?
Zn2 O5 Zn1 114.01(15) 3_656 . ?
P1 O3 Zn2 116.46(18) . . ?
P2 O4 Zn2 156.2(2) . 4_565 ?
P2 O6 Zn1 115.93(19) . 4_565 ?
P1 O1 Zn1 120.14(18) . . ?
P1 O1 Zn1 133.0(2) . 3_656 ?
Zn1 O1 Zn1 102.99(13) . 3_656 ?
P1 O2 Zn2 136.9(2) . 4 ?
C10 O8 H8C 108.6 . . ?
N1 C3 C4 116.7(4) . . ?
N1 C3 H3A 108.2 . . ?
C4 C3 H3A 108.2 . . ?
N1 C3 H3B 108.1 . . ?
C4 C3 H3B 108.0 . . ?
H3A C3 H3B 107.3 . . ?
C6 C4 C5 118.8(5) . . ?
C6 C4 C3 120.6(5) . . ?
C5 C4 C3 120.5(4) . . ?
C7 C5 C4 120.4(5) . . ?
C7 C5 H5A 119.7 . . ?
C4 C5 H5A 119.8 . . ?
C8 C6 C4 121.2(5) . . ?
C8 C6 H6B 119.3 . . ?
C4 C6 H6B 119.5 . . ?
N1 C1 P1 111.4(3) . . ?
N1 C1 H1A 109.4 . . ?
P1 C1 H1A 109.3 . . ?
N1 C1 H1B 109.4 . . ?
P1 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
N1 C2 P2 112.2(3) . . ?
N1 C2 H2B 109.0 . . ?
P2 C2 H2B 109.1 . . ?
N1 C2 H2C 109.3 . . ?
P2 C2 H2C 109.2 . . ?
H2B C2 H2C 107.9 . . ?
C9 C7 C5 120.4(5) . . ?
C9 C7 H7A 119.7 . . ?
C5 C7 H7A 119.9 . . ?
C6 C8 C9 119.6(5) . . ?
C6 C8 H8A 120.2 . . ?
C9 C8 H8A 120.1 . . ?
C7 C9 C8 119.4(5) . . ?
C7 C9 C10 119.2(5) . . ?
C8 C9 C10 121.4(5) . . ?
O7 C10 O8 121.5(6) . . ?
O7 C10 C9 125.4(6) . . ?
O8 C10 C9 113.1(5) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.696
_refine_diff_density_min         -0.889
_refine_diff_density_rms         0.292
_database_code_depnum_ccdc_archive 'CCDC 948672'