# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_GMKDCuphenMDP_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1435205'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2017-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H14 Cu N2 O7 P2'
_chemical_formula_weight         435.74

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'
Cu Cu 0.3201 1.2651 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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'

_cell_length_a                   22.3946(4)
_cell_length_b                   4.88940(10)
_cell_length_c                   16.9441(3)
_cell_angle_alpha                90
_cell_angle_beta                 122.6160(10)
_cell_angle_gamma                90
_cell_volume                     1562.73(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9946
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      24.76

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.852
_exptl_crystal_F_000             884
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.645
_shelx_estimated_absorpt_T_min   0.559
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6592
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27347
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.159
_diffrn_reflns_theta_max         30.555
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             4637
_reflns_number_gt                4360
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.955
_reflns_Friedel_fraction_max     0.954
_reflns_Friedel_fraction_full    0.977

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0232P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2017 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.030(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4637
_refine_ls_number_parameters     238
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0220
_refine_ls_wR_factor_ref         0.0512
_refine_ls_wR_factor_gt          0.0500
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.49248(2) 0.76850(5) 0.54906(2) 0.01966(7) Uani 1 1 d . . . . .
P1 P 0.41616(3) 0.30703(12) 0.40312(5) 0.01907(13) Uani 1 1 d . . . . .
P2 P 0.34965(3) 0.51941(11) 0.50462(4) 0.01915(13) Uani 1 1 d . . . . .
O1 O 0.48178(10) 0.4786(3) 0.46264(15) 0.0265(4) Uani 1 1 d . . . . .
O2 O 0.41872(10) 0.0186(4) 0.43215(14) 0.0282(4) Uani 1 1 d . . . . .
O3 O 0.40045(12) 0.3158(4) 0.29962(15) 0.0313(5) Uani 1 1 d D . . . .
H3O H 0.388(2) 0.173(5) 0.275(3) 0.038 Uiso 1 1 d D U . . .
O4 O 0.42445(10) 0.6132(4) 0.57444(13) 0.0255(4) Uani 1 1 d . . . . .
O5 O 0.32669(12) 0.2648(3) 0.53050(16) 0.0275(4) Uani 1 1 d . . . . .
O6 O 0.29505(11) 0.7501(3) 0.48896(17) 0.0285(4) Uani 1 1 d D . . . .
H6O H 0.3078(18) 0.904(5) 0.496(2) 0.034 Uiso 1 1 d D U . . .
O7 O 0.34860(13) 0.8434(5) 0.20326(17) 0.0357(5) Uani 1 1 d D . . . .
H7A H 0.346(2) 0.808(8) 0.154(2) 0.043 Uiso 1 1 d D U . . .
H7B H 0.357(2) 0.698(5) 0.225(3) 0.043 Uiso 1 1 d D U . . .
N1 N 0.52599(12) 1.0322(4) 0.65716(15) 0.0226(4) Uani 1 1 d . . . . .
N2 N 0.58246(11) 0.9029(4) 0.56067(16) 0.0226(4) Uani 1 1 d . . . . .
C1 C 0.34091(13) 0.4764(5) 0.39315(17) 0.0202(5) Uani 1 1 d . . . . .
H1A H 0.2985 0.3706 0.3520 0.024 Uiso 1 1 calc R U . . .
H1B H 0.3352 0.6546 0.3647 0.024 Uiso 1 1 calc R U . . .
C2 C 0.49609(15) 1.0870(6) 0.7046(2) 0.0307(6) Uani 1 1 d . . . . .
H2 H 0.4565 0.9872 0.6920 0.037 Uiso 1 1 calc R U . . .
C3 C 0.52239(17) 1.2914(7) 0.7737(2) 0.0369(7) Uani 1 1 d . . . . .
H3 H 0.4998 1.3282 0.8052 0.044 Uiso 1 1 calc R U . . .
C4 C 0.58116(16) 1.4357(6) 0.7943(2) 0.0348(7) Uani 1 1 d . . . . .
H4 H 0.5992 1.5695 0.8406 0.042 Uiso 1 1 calc R U . . .
C5 C 0.61445(15) 1.3815(5) 0.74526(19) 0.0267(5) Uani 1 1 d . . . . .
C6 C 0.58394(13) 1.1755(5) 0.67684(18) 0.0219(5) Uani 1 1 d . . . . .
C7 C 0.61471(13) 1.1065(5) 0.62461(18) 0.0219(5) Uani 1 1 d . . . . .
C8 C 0.67553(15) 1.2428(5) 0.6405(2) 0.0276(6) Uani 1 1 d . . . . .
C9 C 0.70304(16) 1.1594(7) 0.5874(2) 0.0374(7) Uani 1 1 d . . . . .
H9 H 0.7427 1.2460 0.5946 0.045 Uiso 1 1 calc R U . . .
C10 C 0.67142(17) 0.9502(7) 0.5249(2) 0.0389(7) Uani 1 1 d . . . . .
H10 H 0.6902 0.8899 0.4907 0.047 Uiso 1 1 calc R U . . .
C11 C 0.61061(16) 0.8267(6) 0.5126(2) 0.0312(6) Uani 1 1 d . . . . .
H11 H 0.5892 0.6861 0.4691 0.037 Uiso 1 1 calc R U . . .
C12 C 0.70529(15) 1.4546(6) 0.7103(2) 0.0331(7) Uani 1 1 d . . . . .
H12 H 0.7452 1.5486 0.7214 0.040 Uiso 1 1 calc R U . . .
C13 C 0.67617(15) 1.5197(6) 0.7603(2) 0.0323(6) Uani 1 1 d . . . . .
H13 H 0.6967 1.6568 0.8053 0.039 Uiso 1 1 calc R U . . .


_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
Cu1 O4 1.9466(19) . ?
Cu1 O1 1.9576(19) . ?
Cu1 N1 2.025(2) . ?
Cu1 N2 2.026(2) . ?
Cu1 O2 2.1495(19) 1_565 ?
P1 O2 1.4845(18) . ?
P1 O1 1.5110(19) . ?
P1 O3 1.592(2) . ?
P1 C1 1.802(3) . ?
P2 O5 1.4998(18) . ?
P2 O4 1.5098(19) . ?
P2 O6 1.577(2) . ?
P2 C1 1.803(3) . ?
O2 Cu1 2.1494(19) 1_545 ?
O3 H3O 0.78(2) . ?
O6 H6O 0.79(2) . ?
O7 H7A 0.82(3) . ?
O7 H7B 0.78(2) . ?
N1 C2 1.322(4) . ?
N1 C6 1.349(3) . ?
N2 C11 1.324(4) . ?
N2 C7 1.358(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.404(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.362(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.409(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.404(4) . ?
C5 C13 1.432(4) . ?
C6 C7 1.424(4) . ?
C7 C8 1.406(4) . ?
C8 C9 1.399(5) . ?
C8 C12 1.437(4) . ?
C9 C10 1.363(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.398(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.357(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?

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
O4 Cu1 O1 95.04(8) . . ?
O4 Cu1 N1 90.07(9) . . ?
O1 Cu1 N1 166.93(9) . . ?
O4 Cu1 N2 163.97(8) . . ?
O1 Cu1 N2 91.25(9) . . ?
N1 Cu1 N2 80.87(9) . . ?
O4 Cu1 O2 96.97(8) . 1_565 ?
O1 Cu1 O2 89.95(8) . 1_565 ?
N1 Cu1 O2 101.39(8) . 1_565 ?
N2 Cu1 O2 97.76(9) . 1_565 ?
O2 P1 O1 117.15(11) . . ?
O2 P1 O3 109.66(12) . . ?
O1 P1 O3 106.15(12) . . ?
O2 P1 C1 109.57(12) . . ?
O1 P1 C1 109.36(11) . . ?
O3 P1 C1 104.13(12) . . ?
O5 P2 O4 115.68(12) . . ?
O5 P2 O6 106.61(12) . . ?
O4 P2 O6 110.29(11) . . ?
O5 P2 C1 110.41(11) . . ?
O4 P2 C1 107.72(11) . . ?
O6 P2 C1 105.69(12) . . ?
P1 O1 Cu1 125.74(12) . . ?
P1 O2 Cu1 135.98(12) . 1_545 ?
P1 O3 H3O 111(3) . . ?
P2 O4 Cu1 127.97(11) . . ?
P2 O6 H6O 118(3) . . ?
H7A O7 H7B 100(4) . . ?
C2 N1 C6 118.7(2) . . ?
C2 N1 Cu1 128.1(2) . . ?
C6 N1 Cu1 113.10(18) . . ?
C11 N2 C7 118.2(2) . . ?
C11 N2 Cu1 128.87(19) . . ?
C7 N2 Cu1 112.89(17) . . ?
P1 C1 P2 112.79(13) . . ?
P1 C1 H1A 109.0 . . ?
P2 C1 H1A 109.0 . . ?
P1 C1 H1B 109.0 . . ?
P2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
N1 C2 C3 121.9(3) . . ?
N1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 116.4(3) . . ?
C6 C5 C13 118.6(3) . . ?
C4 C5 C13 125.0(3) . . ?
N1 C6 C5 123.5(3) . . ?
N1 C6 C7 116.5(2) . . ?
C5 C6 C7 120.0(2) . . ?
N2 C7 C8 123.0(3) . . ?
N2 C7 C6 116.2(2) . . ?
C8 C7 C6 120.8(2) . . ?
C9 C8 C7 117.1(3) . . ?
C9 C8 C12 124.8(3) . . ?
C7 C8 C12 118.1(3) . . ?
C10 C9 C8 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 119.8(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
N2 C11 C10 122.3(3) . . ?
N2 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C13 C12 C8 121.1(3) . . ?
C13 C12 H12 119.4 . . ?
C8 C12 H12 119.4 . . ?
C12 C13 C5 121.4(3) . . ?
C12 C13 H13 119.3 . . ?
C5 C13 H13 119.3 . . ?

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.050

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_GMKDZ1_0m
_database_code_depnum_ccdc_archive 'CCDC 1435206'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2017-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H18 Mn N2 O8 P2'
_chemical_formula_weight         435.16

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   12.3487(3)
_cell_length_b                   14.3471(4)
_cell_length_c                   10.0005(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.5780(10)
_cell_angle_gamma                90
_cell_volume                     1689.04(8)
_cell_formula_units_Z            4
_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_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_F_000             892
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.016
_shelx_estimated_absorpt_T_min   0.675
_shelx_estimated_absorpt_T_max   0.951
_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_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23096
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.238
_diffrn_reflns_theta_max         29.701
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2388
_reflns_number_gt                2088
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0436P)²+0.8375P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2388
_refine_ls_number_parameters     123
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0754
_refine_ls_wR_factor_gt          0.0711
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.043
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.0000 0.23870(2) 0.2500 0.02181(9) Uani 1 2 d S T P . .
P1 P -0.04097(3) 0.35346(2) -0.06574(3) 0.02403(10) Uani 1 1 d . . . . .
O1 O -0.05995(9) 0.31945(7) 0.06668(10) 0.0307(2) Uani 1 1 d . . . . .
O2 O 0.08316(9) 0.32380(8) -0.06255(11) 0.0332(2) Uani 1 1 d D . . . .
H2 H 0.1008(16) 0.3215(14) -0.1336(17) 0.040 Uiso 1 1 d D U . . .
O3 O -0.12489(9) 0.32084(8) -0.20166(10) 0.0331(2) Uani 1 1 d . . . . .
O4 O -0.16667(10) 0.25837(10) 0.28855(13) 0.0404(3) Uani 1 1 d D . . . .
H4A H -0.2231(15) 0.2303(14) 0.257(2) 0.049 Uiso 1 1 d D U . . .
H4B H -0.1589(18) 0.2786(14) 0.3644(17) 0.049 Uiso 1 1 d D U . . .
N1 N 0.08047(11) 0.10877(9) 0.37285(14) 0.0327(3) Uani 1 1 d . . . . .
C1 C -0.04179(12) 0.47849(10) -0.06541(14) 0.0294(3) Uani 1 1 d . . . . .
H1A H -0.0234 0.5006 -0.1476 0.035 Uiso 1 1 calc R U . . .
H1B H -0.1178 0.4999 -0.0725 0.035 Uiso 1 1 calc R U . . .
C2 C 0.04449(13) 0.02447(10) 0.31900(18) 0.0357(3) Uani 1 1 d . . . . .
C3 C 0.08958(18) -0.05611(13) 0.3925(3) 0.0576(6) Uani 1 1 d . . . . .
H3 H 0.0641 -0.1143 0.3552 0.069 Uiso 1 1 calc R U . . .
C4 C 0.17162(18) -0.04936(18) 0.5198(3) 0.0696(8) Uani 1 1 d . . . . .
H4 H 0.2015 -0.1029 0.5699 0.084 Uiso 1 1 calc R U . . .
C5 C 0.20908(16) 0.03626(17) 0.5724(2) 0.0585(6) Uani 1 1 d . . . . .
H5 H 0.2654 0.0422 0.6581 0.070 Uiso 1 1 calc R U . . .
C6 C 0.16159(15) 0.11435(14) 0.49571(19) 0.0438(4) Uani 1 1 d . . . . .
H6 H 0.1873 0.1729 0.5312 0.053 Uiso 1 1 calc R U . . .


_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
Mn1 O1 2.1051(10) 2 ?
Mn1 O1 2.1051(10) . ?
Mn1 O4 2.2234(12) 2 ?
Mn1 O4 2.2234(12) . ?
Mn1 N1 2.2878(12) . ?
Mn1 N1 2.2878(12) 2 ?
P1 O1 1.4947(10) . ?
P1 O3 1.5132(10) . ?
P1 O2 1.5818(11) . ?
P1 C1 1.7938(15) . ?
O2 H2 0.804(15) . ?
O4 H4A 0.785(15) . ?
O4 H4B 0.791(15) . ?
N1 C6 1.333(2) . ?
N1 C2 1.344(2) . ?
C1 C1 1.530(3) 5_565 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.393(2) . ?
C2 C2 1.482(3) 2 ?
C3 C4 1.370(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.361(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?

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 Mn1 O1 113.22(6) 2 . ?
O1 Mn1 O4 88.89(4) 2 2 ?
O1 Mn1 O4 83.08(4) . 2 ?
O1 Mn1 O4 83.09(4) 2 . ?
O1 Mn1 O4 88.89(4) . . ?
O4 Mn1 O4 165.41(7) 2 . ?
O1 Mn1 N1 89.96(4) 2 . ?
O1 Mn1 N1 153.84(5) . . ?
O4 Mn1 N1 85.52(5) 2 . ?
O4 Mn1 N1 106.56(5) . . ?
O1 Mn1 N1 153.84(5) 2 2 ?
O1 Mn1 N1 89.96(4) . 2 ?
O4 Mn1 N1 106.56(5) 2 2 ?
O4 Mn1 N1 85.52(5) . 2 ?
N1 Mn1 N1 70.87(7) . 2 ?
O1 P1 O3 116.54(6) . . ?
O1 P1 O2 107.73(6) . . ?
O3 P1 O2 109.36(6) . . ?
O1 P1 C1 108.81(6) . . ?
O3 P1 C1 107.95(6) . . ?
O2 P1 C1 105.96(7) . . ?
P1 O1 Mn1 147.48(7) . . ?
P1 O2 H2 120.8(14) . . ?
Mn1 O4 H4A 128.3(16) . . ?
Mn1 O4 H4B 111.3(15) . . ?
H4A O4 H4B 114(2) . . ?
C6 N1 C2 119.27(15) . . ?
C6 N1 Mn1 121.99(12) . . ?
C2 N1 Mn1 118.73(10) . . ?
C1 C1 P1 113.71(13) 5_565 . ?
C1 C1 H1A 108.8 5_565 . ?
P1 C1 H1A 108.8 . . ?
C1 C1 H1B 108.8 5_565 . ?
P1 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
N1 C2 C3 120.31(18) . . ?
N1 C2 C2 115.83(9) . 2 ?
C3 C2 C2 123.87(13) . 2 ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 119.51(18) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 118.6(2) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
N1 C6 C5 122.5(2) . . ?
N1 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?

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
O3 P1 O1 Mn1 114.66(12) . . . . ?
O2 P1 O1 Mn1 -8.62(15) . . . . ?
C1 P1 O1 Mn1 -123.07(13) . . . . ?
O1 P1 C1 C1 53.98(16) . . . 5_565 ?
O3 P1 C1 C1 -178.69(13) . . . 5_565 ?
O2 P1 C1 C1 -61.62(15) . . . 5_565 ?
C6 N1 C2 C3 1.6(2) . . . . ?
Mn1 N1 C2 C3 -178.43(13) . . . . ?
C6 N1 C2 C2 -179.02(16) . . . 2 ?
Mn1 N1 C2 C2 1.0(2) . . . 2 ?
N1 C2 C3 C4 -0.5(3) . . . . ?
C2 C2 C3 C4 -179.86(19) 2 . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C2 N1 C6 C5 -1.5(3) . . . . ?
Mn1 N1 C6 C5 178.52(14) . . . . ?
C4 C5 C6 N1 0.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 O1 0.93 2.63 3.186(2) 118.9 2
O4 H4B O2 0.791(15) 2.025(16) 2.7832(15) 160(2) 2
O4 H4A O3 0.785(15) 1.934(15) 2.7057(15) 168(2) 7_455
O2 H2 O3 0.804(15) 1.760(15) 2.5616(14) 174(2) 2_554
C6 H6 O1 0.93 2.63 3.186(2) 118.9 2
O4 H4B O2 0.791(15) 2.025(16) 2.7832(15) 160(2) 2
O4 H4A O3 0.785(15) 1.934(15) 2.7057(15) 168(2) 7_455
O2 H2 O3 0.804(15) 1.760(15) 2.5616(14) 174(2) 2_554
C6 H6 O1 0.93 2.63 3.186(2) 118.9 2
O4 H4B O2 0.791(15) 2.025(16) 2.7832(15) 160(2) 2
O4 H4A O3 0.785(15) 1.934(15) 2.7057(15) 168(2) 7_455
O2 H2 O3 0.804(15) 1.760(15) 2.5616(14) 174(2) 2_554
C6 H6 O1 0.93 2.63 3.186(2) 118.9 2
O4 H4B O2 0.791(15) 2.025(16) 2.7832(15) 160(2) 2
O4 H4A O3 0.785(15) 1.934(15) 2.7057(15) 168(2) 7_455
O2 H2 O3 0.804(15) 1.760(15) 2.5616(14) 174(2) 2_554
C6 H6 O1 0.93 2.63 3.186(2) 118.9 2
O4 H4B O2 0.791(15) 2.025(16) 2.7832(15) 160(2) 2
O4 H4A O3 0.785(15) 1.934(15) 2.7057(15) 168(2) 7_455
O2 H2 O3 0.804(15) 1.760(15) 2.5616(14) 174(2) 2_554
C6 H6 O1 0.93 2.63 3.186(2) 118.9 2
O4 H4B O2 0.791(15) 2.025(16) 2.7832(15) 160(2) 2
O4 H4A O3 0.785(15) 1.934(15) 2.7057(15) 168(2) 7_455
O2 H2 O3 0.804(15) 1.760(15) 2.5616(14) 174(2) 2_554
C6 H6 O1 0.93 2.63 3.186(2) 118.9 2
O4 H4B O2 0.791(15) 2.025(16) 2.7832(15) 160(2) 2
O4 H4A O3 0.785(15) 1.934(15) 2.7057(15) 168(2) 7_455
O2 H2 O3 0.804(15) 1.760(15) 2.5616(14) 174(2) 2_554
C6 H6 O1 0.93 2.63 3.186(2) 118.9 2
O4 H4B O2 0.791(15) 2.025(16) 2.7832(15) 160(2) 2
O4 H4A O3 0.785(15) 1.934(15) 2.7057(15) 168(2) 7_455
O2 H2 O3 0.804(15) 1.760(15) 2.5616(14) 174(2) 2_554
O4 H4B O2 0.791(15) 2.025(16) 2.7832(15) 160(2) 2
O4 H4A O3 0.785(15) 1.934(15) 2.7057(15) 168(2) 7_455
C6 H6 O1 0.93 2.63 3.186(2) 118.9 2
C6 H6 O1 0.93 2.63 3.186(2) 118.9 2
O4 H4A O3 0.785(15) 1.934(15) 2.7057(15) 168(2) 7_455
O4 H4B O2 0.791(15) 2.025(16) 2.7832(15) 160(2) 2
O2 H2 O3 0.804(15) 1.760(15) 2.5616(14) 174(2) 2_554
O2 H2 O3 0.804(15) 1.760(15) 2.5616(14) 174(2) 2_554
O4 H4A O3 0.785(15) 1.934(15) 2.7057(15) 168(2) 7_455
O4 H4B O2 0.791(15) 2.025(16) 2.7832(15) 160(2) 2
C6 H6 O1 0.93 2.63 3.186(2) 118.9 2
O2 H2 O3 0.804(15) 1.760(15) 2.5616(14) 174(2) 2_554
O4 H4A O3 0.785(15) 1.934(15) 2.7057(15) 168(2) 7_455
O4 H4B O2 0.791(15) 2.025(16) 2.7832(15) 160(2) 2
C6 H6 O1 0.93 2.63 3.186(2) 118.9 2
O2 H2 O3 0.804(15) 1.760(15) 2.5616(14) 174(2) 2_554
O4 H4A O3 0.785(15) 1.934(15) 2.7057(15) 168(2) 7_455
O4 H4B O2 0.791(15) 2.025(16) 2.7832(15) 160(2) 2
C6 H6 O1 0.93 2.63 3.186(2) 118.9 2
O2 H2 O3 0.804(15) 1.760(15) 2.5616(14) 174(2) 2_554
O4 H4A O3 0.785(15) 1.934(15) 2.7057(15) 168(2) 7_455
O4 H4B O2 0.791(15) 2.025(16) 2.7832(15) 160(2) 2
C6 H6 O1 0.93 2.63 3.186(2) 118.9 2
O2 H2 O3 0.804(15) 1.760(15) 2.5616(14) 174(2) 2_554
O4 H4A O3 0.785(15) 1.934(15) 2.7057(15) 168(2) 7_455
O4 H4B O2 0.791(15) 2.025(16) 2.7832(15) 160(2) 2
C6 H6 O1 0.93 2.63 3.186(2) 118.9 2
O2 H2 O3 0.804(15) 1.760(15) 2.5616(14) 174(2) 2_554
O4 H4A O3 0.785(15) 1.934(15) 2.7057(15) 168(2) 7_455
O4 H4B O2 0.791(15) 2.025(16) 2.7832(15) 160(2) 2
C6 H6 O1 0.93 2.63 3.186(2) 118.9 2
O2 H2 O3 0.804(15) 1.760(15) 2.5616(14) 174(2) 2_554
O4 H4A O3 0.785(15) 1.934(15) 2.7057(15) 168(2) 7_455
O4 H4B O2 0.791(15) 2.025(16) 2.7832(15) 160(2) 2
C6 H6 O1 0.93 2.63 3.186(2) 118.9 2

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.062

_shelxl_version_number           2013-2

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_gmkd05_0m
_database_code_depnum_ccdc_archive 'CCDC 1435207'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2017-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H14 N2 O6 P2 Zn'
_chemical_formula_weight         409.56

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           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.5335(2)
_cell_length_b                   10.6895(3)
_cell_length_c                   12.6347(4)
_cell_angle_alpha                95.967(2)
_cell_angle_beta                 90.237(2)
_cell_angle_gamma                103.332(2)
_cell_volume                     722.96(4)
_cell_formula_units_Z            2
_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          0.28
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.881
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    1.953
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.6108
_exptl_absorpt_correction_T_max  0.8754
_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_reflns_number            28580
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         28.84
_reflns_number_total             3780
_reflns_number_gt                3265
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0252P)²+0.4314P] 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         3780
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0621
_refine_ls_wR_factor_gt          0.0587
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.28797(4) 0.28892(2) 0.210828(16) 0.01483(7) Uani 1 1 d . . .
P1 P 0.31055(9) 0.10635(5) 0.41210(4) 0.01731(11) Uani 1 1 d . . .
P2 P 0.74089(8) 0.13504(5) 0.12186(4) 0.01405(10) Uani 1 1 d . . .
O1 O 0.3076(3) 0.21418(14) 0.34628(11) 0.0255(3) Uani 1 1 d . . .
O2 O 0.4739(3) 0.17004(15) 0.51538(12) 0.0252(3) Uani 1 1 d . . .
O3 O 0.4071(3) -0.00571(14) 0.36031(11) 0.0238(3) Uani 1 1 d . . .
O4 O 0.5693(2) 0.22310(13) 0.14514(11) 0.0228(3) Uani 1 1 d . . .
O5 O 0.7285(3) 0.03824(15) 0.20813(12) 0.0254(3) Uani 1 1 d . . .
H5 H 0.630(5) 0.031(3) 0.245(2) 0.030 Uiso 1 1 d . . .
O6 O 1.0109(2) 0.20083(13) 0.11088(10) 0.0205(3) Uani 1 1 d . . .
H6 H 0.498(4) 0.119(2) 0.5529(19) 0.025 Uiso 1 1 d . . .
N1 N 0.0910(3) 0.42033(16) 0.29631(13) 0.0204(3) Uani 1 1 d . . .
N2 N 0.4714(3) 0.47842(16) 0.17236(13) 0.0199(3) Uani 1 1 d . . .
C1 C -0.1061(4) 0.3814(2) 0.35558(16) 0.0239(4) Uani 1 1 d . . .
H1 H -0.1584 0.2939 0.3637 0.029 Uiso 1 1 calc R . .
C2 C -0.2345(4) 0.4660(2) 0.40509(17) 0.0307(5) Uani 1 1 d . . .
H2 H -0.3720 0.4359 0.4453 0.037 Uiso 1 1 calc R . .
C3 C -0.1562(4) 0.5954(2) 0.39408(18) 0.0334(5) Uani 1 1 d . . .
H3 H -0.2398 0.6544 0.4270 0.040 Uiso 1 1 calc R . .
C4 C 0.0483(4) 0.6371(2) 0.33353(18) 0.0299(5) Uani 1 1 d . . .
H4 H 0.1053 0.7245 0.3258 0.036 Uiso 1 1 calc R . .
C5 C 0.1678(4) 0.54627(19) 0.28416(15) 0.0211(4) Uani 1 1 d . . .
C6 C 0.3836(4) 0.57949(19) 0.21459(15) 0.0212(4) Uani 1 1 d . . .
C7 C 0.4914(5) 0.7045(2) 0.1945(2) 0.0337(5) Uani 1 1 d . . .
H7 H 0.4299 0.7732 0.2254 0.040 Uiso 1 1 calc R . .
C8 C 0.6911(5) 0.7264(2) 0.1283(2) 0.0383(6) Uani 1 1 d . . .
H8 H 0.7641 0.8098 0.1132 0.046 Uiso 1 1 calc R . .
C9 C 0.7807(4) 0.6228(2) 0.08468(19) 0.0332(5) Uani 1 1 d . . .
H9 H 0.9144 0.6349 0.0395 0.040 Uiso 1 1 calc R . .
C10 C 0.6675(4) 0.5006(2) 0.10973(17) 0.0265(4) Uani 1 1 d . . .
H10 H 0.7303 0.4310 0.0819 0.032 Uiso 1 1 calc R . .
C11 C 0.0048(3) 0.0470(2) 0.45801(16) 0.0233(4) Uani 1 1 d . . .
H11A H -0.0598 0.1196 0.4878 0.028 Uiso 1 1 calc R . .
H11B H -0.1023 0.0037 0.3978 0.028 Uiso 1 1 calc R . .
C12 C 0.6371(3) 0.03621(19) -0.00074(14) 0.0180(4) Uani 1 1 d . . .
H12A H 0.6592 0.0904 -0.0586 0.022 Uiso 1 1 calc R . .
H12B H 0.7389 -0.0262 -0.0141 0.022 Uiso 1 1 calc R . .


_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 1.9753(14) . ?
Zn1 O6 1.9755(12) 1_455 ?
Zn1 O4 2.0006(13) . ?
Zn1 N2 2.1518(17) . ?
Zn1 N1 2.1744(16) . ?
P1 O1 1.4927(14) . ?
P1 O3 1.5112(15) . ?
P1 O2 1.5827(15) . ?
P1 C11 1.7866(19) . ?
P2 O4 1.4935(14) . ?
P2 O6 1.5113(13) . ?
P2 O5 1.5703(15) . ?
P2 C12 1.7938(18) . ?
O2 H6 0.80(2) . ?
O5 H5 0.72(3) . ?
O6 Zn1 1.9755(12) 1_655 ?
N1 C1 1.336(3) . ?
N1 C5 1.340(3) . ?
N2 C10 1.337(3) . ?
N2 C6 1.346(2) . ?
C1 C2 1.377(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.373(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.484(3) . ?
C6 C7 1.381(3) . ?
C7 C8 1.381(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.380(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.381(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C11 1.528(4) 2_556 ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C12 1.537(3) 2_655 ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

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 O6 116.81(6) . 1_455 ?
O1 Zn1 O4 94.92(6) . . ?
O6 Zn1 O4 101.05(6) 1_455 . ?
O1 Zn1 N2 127.91(6) . . ?
O6 Zn1 N2 113.46(6) 1_455 . ?
O4 Zn1 N2 88.12(6) . . ?
O1 Zn1 N1 87.08(6) . . ?
O6 Zn1 N1 96.21(6) 1_455 . ?
O4 Zn1 N1 159.45(6) . . ?
N2 Zn1 N1 74.74(6) . . ?
O1 P1 O3 116.74(8) . . ?
O1 P1 O2 105.90(9) . . ?
O3 P1 O2 109.86(8) . . ?
O1 P1 C11 109.02(9) . . ?
O3 P1 C11 109.23(9) . . ?
O2 P1 C11 105.47(9) . . ?
O4 P2 O6 115.68(8) . . ?
O4 P2 O5 111.79(8) . . ?
O6 P2 O5 107.54(8) . . ?
O4 P2 C12 108.12(8) . . ?
O6 P2 C12 107.65(8) . . ?
O5 P2 C12 105.53(9) . . ?
P1 O1 Zn1 154.05(10) . . ?
P1 O2 H6 113.2(18) . . ?
P2 O4 Zn1 158.43(10) . . ?
P2 O5 H5 120(2) . . ?
P2 O6 Zn1 135.21(8) . 1_655 ?
C1 N1 C5 119.18(17) . . ?
C1 N1 Zn1 123.57(14) . . ?
C5 N1 Zn1 117.19(13) . . ?
C10 N2 C6 118.71(18) . . ?
C10 N2 Zn1 123.52(14) . . ?
C6 N2 Zn1 117.77(13) . . ?
N1 C1 C2 122.5(2) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.2(2) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 119.0(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.2(2) . . ?
N1 C5 C6 115.17(17) . . ?
C4 C5 C6 123.64(19) . . ?
N2 C6 C7 121.5(2) . . ?
N2 C6 C5 115.12(17) . . ?
C7 C6 C5 123.36(19) . . ?
C8 C7 C6 119.4(2) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C9 C8 C7 119.1(2) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 118.5(2) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
N2 C10 C9 122.7(2) . . ?
N2 C10 H10 118.6 . . ?
C9 C10 H10 118.6 . . ?
C11 C11 P1 113.32(18) 2_556 . ?
C11 C11 H11A 108.9 2_556 . ?
P1 C11 H11A 108.9 . . ?
C11 C11 H11B 108.9 2_556 . ?
P1 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C12 C12 P2 112.51(17) 2_655 . ?
C12 C12 H12A 109.1 2_655 . ?
P2 C12 H12A 109.1 . . ?
C12 C12 H12B 109.1 2_655 . ?
P2 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?

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
O3 P1 O1 Zn1 28.1(2) . . . . ?
O2 P1 O1 Zn1 150.7(2) . . . . ?
C11 P1 O1 Zn1 -96.3(2) . . . . ?
O6 Zn1 O1 P1 50.2(2) 1_455 . . . ?
O4 Zn1 O1 P1 -54.9(2) . . . . ?
N2 Zn1 O1 P1 -146.3(2) . . . . ?
N1 Zn1 O1 P1 145.6(2) . . . . ?
O6 P2 O4 Zn1 -140.7(2) . . . . ?
O5 P2 O4 Zn1 -17.2(3) . . . . ?
C12 P2 O4 Zn1 98.6(3) . . . . ?
O1 Zn1 O4 P2 31.4(3) . . . . ?
O6 Zn1 O4 P2 -87.2(3) 1_455 . . . ?
N2 Zn1 O4 P2 159.3(3) . . . . ?
N1 Zn1 O4 P2 126.2(2) . . . . ?
O4 P2 O6 Zn1 76.60(14) . . . 1_655 ?
O5 P2 O6 Zn1 -49.12(14) . . . 1_655 ?
C12 P2 O6 Zn1 -162.40(12) . . . 1_655 ?
O1 Zn1 N1 C1 -51.26(15) . . . . ?
O6 Zn1 N1 C1 65.41(16) 1_455 . . . ?
O4 Zn1 N1 C1 -147.49(17) . . . . ?
N2 Zn1 N1 C1 178.08(16) . . . . ?
O1 Zn1 N1 C5 131.70(14) . . . . ?
O6 Zn1 N1 C5 -111.63(14) 1_455 . . . ?
O4 Zn1 N1 C5 35.5(3) . . . . ?
N2 Zn1 N1 C5 1.04(13) . . . . ?
O1 Zn1 N2 C10 105.05(16) . . . . ?
O6 Zn1 N2 C10 -90.95(16) 1_455 . . . ?
O4 Zn1 N2 C10 10.28(16) . . . . ?
N1 Zn1 N2 C10 178.83(17) . . . . ?
O1 Zn1 N2 C6 -74.46(16) . . . . ?
O6 Zn1 N2 C6 89.53(14) 1_455 . . . ?
O4 Zn1 N2 C6 -169.24(14) . . . . ?
N1 Zn1 N2 C6 -0.69(13) . . . . ?
C5 N1 C1 C2 0.0(3) . . . . ?
Zn1 N1 C1 C2 -177.00(15) . . . . ?
N1 C1 C2 C3 -0.6(3) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C1 N1 C5 C4 1.0(3) . . . . ?
Zn1 N1 C5 C4 178.21(15) . . . . ?
C1 N1 C5 C6 -178.39(17) . . . . ?
Zn1 N1 C5 C6 -1.2(2) . . . . ?
C3 C4 C5 N1 -1.4(3) . . . . ?
C3 C4 C5 C6 177.96(19) . . . . ?
C10 N2 C6 C7 0.1(3) . . . . ?
Zn1 N2 C6 C7 179.59(16) . . . . ?
C10 N2 C6 C5 -179.24(17) . . . . ?
Zn1 N2 C6 C5 0.3(2) . . . . ?
N1 C5 C6 N2 0.6(2) . . . . ?
C4 C5 C6 N2 -178.80(18) . . . . ?
N1 C5 C6 C7 -178.67(19) . . . . ?
C4 C5 C6 C7 1.9(3) . . . . ?
N2 C6 C7 C8 1.1(3) . . . . ?
C5 C6 C7 C8 -179.7(2) . . . . ?
C6 C7 C8 C9 -0.9(4) . . . . ?
C7 C8 C9 C10 -0.4(4) . . . . ?
C6 N2 C10 C9 -1.4(3) . . . . ?
Zn1 N2 C10 C9 179.05(16) . . . . ?
C8 C9 C10 N2 1.6(3) . . . . ?
O1 P1 C11 C11 -169.7(2) . . . 2_556 ?
O3 P1 C11 C11 61.6(2) . . . 2_556 ?
O2 P1 C11 C11 -56.4(2) . . . 2_556 ?
O4 P2 C12 C12 -54.4(2) . . . 2_655 ?
O6 P2 C12 C12 180.00(18) . . . 2_655 ?
O5 P2 C12 C12 65.4(2) . . . 2_655 ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        28.84
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.074
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound_5
_database_code_depnum_ccdc_archive 'CCDC 1521331'
_audit_update_record             
;
2016-12-07 deposited with the CCDC.
2017-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H22 N2 Ni O10 P2'
_chemical_formula_weight         498.98

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.20460(10)
_cell_length_b                   19.6744(2)
_cell_length_c                   13.64070(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1933.52(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9900
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      31.91

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.227
_shelx_estimated_absorpt_T_min   0.579
_shelx_estimated_absorpt_T_max   0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6471
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37488
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.817
_diffrn_reflns_theta_max         28.699
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2570
_reflns_number_gt                2250
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0335P)²+0.6222P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2570
_refine_ls_number_parameters     199
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0243
_refine_ls_wR_factor_ref         0.0643
_refine_ls_wR_factor_gt          0.0607
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.95097(3) 0.7500 0.56892(2) 0.02316(8) Uani 1 2 d S T P . .
P1A P -0.0104(6) 0.5780(3) 0.8844(5) 0.0257(9) Uani 0.5 1 d . . P A 1
O1A O -0.0595(3) 0.64087(10) 0.94567(18) 0.0349(5) Uani 0.5 1 d . . P A 1
O2A O -0.2005(7) 0.5468(3) 0.8450(4) 0.0404(10) Uani 0.5 1 d D . P A 1
H2A H -0.224(6) 0.553(2) 0.7871(16) 0.048 Uiso 0.5 1 d D U P B 1
O3A O 0.1177(4) 0.59390(14) 0.80321(17) 0.0356(6) Uani 0.5 1 d . . P A 1
C1A C 0.0699(4) 0.51272(13) 0.9626(2) 0.0259(5) Uani 0.5 1 d . . P A 1
H1A1 H 0.1088 0.4746 0.9225 0.031 Uiso 0.5 1 calc R U P A 1
H1A2 H 0.1784 0.5292 0.9974 0.031 Uiso 0.5 1 calc R U P A 1
P1B P -0.0049(7) 0.5753(3) 0.8772(5) 0.0247(8) Uani 0.5 1 d . . P C 2
O1B O -0.0427(3) 0.64853(10) 0.87825(18) 0.0326(4) Uani 0.5 1 d . . P C 2
O2B O -0.1501(7) 0.5321(2) 0.8204(4) 0.0456(12) Uani 0.5 1 d . . P C 2
O3B O 0.1924(3) 0.55906(13) 0.83683(17) 0.0404(5) Uani 0.5 1 d D . P C 2
H3B H 0.147(8) 0.581(3) 0.794(3) 0.048 Uiso 0.5 1 d D U P D 2
C1B C -0.0112(4) 0.53868(13) 0.9980(2) 0.0238(5) Uani 0.5 1 d . . P C 2
H1B1 H 0.0868 0.5591 1.0368 0.029 Uiso 0.5 1 calc R U P C 2
H1B2 H -0.1285 0.5506 1.0283 0.029 Uiso 0.5 1 calc R U P C 2
O4 O 1.2217(2) 0.7500 0.60638(17) 0.0488(5) Uani 1 2 d DS T P . .
H4A H 1.286(3) 0.7847(8) 0.6014(15) 0.059 Uiso 1 1 d D U . . .
O5 O 0.91686(18) 0.82601(7) 0.66982(10) 0.0474(3) Uani 1 1 d D . . . .
H5A H 0.981(3) 0.8315(11) 0.7170(13) 0.057 Uiso 1 1 d D U . . .
H5B H 0.830(3) 0.8524(10) 0.6700(16) 0.057 Uiso 1 1 d D U . . .
O6 O 0.6698(2) 0.7500 0.54254(11) 0.0308(3) Uani 1 2 d DS T P . .
H6O H 0.611(3) 0.7838(8) 0.5563(12) 0.037 Uiso 1 1 d D U . . .
N1 N 0.98418(17) 0.81792(6) 0.45362(9) 0.0297(3) Uani 1 1 d . . . . .
C2 C 0.9943(2) 0.88531(8) 0.45560(15) 0.0426(4) Uani 1 1 d . . . . .
H2 H 0.9959 0.9073 0.5160 0.051 Uiso 1 1 calc R U . . .
C3 C 1.0026(3) 0.92435(9) 0.37035(18) 0.0569(6) Uani 1 1 d . . . . .
H3 H 1.0100 0.9715 0.3744 0.068 Uiso 1 1 calc R U . . .
C4 C 0.9997(3) 0.89337(12) 0.28176(17) 0.0596(6) Uani 1 1 d . . . . .
H4 H 1.0034 0.9192 0.2247 0.072 Uiso 1 1 calc R U . . .
C5 C 0.9912(3) 0.82191(11) 0.27618(13) 0.0471(4) Uani 1 1 d . . . . .
C6 C 0.98509(19) 0.78663(8) 0.36549(11) 0.0311(3) Uani 1 1 d . . . . .
C7 C 0.9909(3) 0.78380(13) 0.18650(14) 0.0658(6) Uani 1 1 d . . . . .
H7 H 0.9907 0.8069 0.1270 0.079 Uiso 1 1 calc R U . . .


_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
Ni1 O4 2.0166(17) . ?
Ni1 O5 2.0471(11) 7_575 ?
Ni1 O5 2.0472(11) . ?
Ni1 O6 2.0577(14) . ?
Ni1 N1 2.0776(12) . ?
Ni1 N1 2.0776(12) 7_575 ?
P1A O3A 1.476(7) . ?
P1A O1A 1.534(8) . ?
P1A O2A 1.595(7) . ?
P1A C1A 1.767(5) . ?
O2A H2A 0.814(19) . ?
C1A C1A 1.518(6) 5_567 ?
C1A H1A1 0.9700 . ?
C1A H1A2 0.9700 . ?
P1B O1B 1.467(5) . ?
P1B O2B 1.555(8) . ?
P1B O3B 1.558(7) . ?
P1B C1B 1.798(7) . ?
P1B H3B 1.59(6) . ?
O3B H3B 0.80(2) . ?
C1B C1B 1.531(5) 5_567 ?
C1B H1B1 0.9700 . ?
C1B H1B2 0.9700 . ?
O4 H4A 0.826(15) . ?
O5 H5A 0.798(15) . ?
O5 H5B 0.814(15) . ?
O6 H6O 0.811(14) . ?
N1 C2 1.3282(19) . ?
N1 C6 1.3507(19) . ?
C2 C3 1.395(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.354(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.409(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.403(2) . ?
C5 C7 1.435(3) . ?
C6 C6 1.441(3) 7_575 ?
C7 C7 1.330(5) 7_575 ?
C7 H7 0.9300 . ?

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
O4 Ni1 O5 86.89(6) . 7_575 ?
O4 Ni1 O5 86.89(6) . . ?
O5 Ni1 O5 93.85(8) 7_575 . ?
O4 Ni1 O6 175.39(8) . . ?
O5 Ni1 O6 89.96(5) 7_575 . ?
O5 Ni1 O6 89.97(5) . . ?
O4 Ni1 N1 94.61(6) . . ?
O5 Ni1 N1 173.02(5) 7_575 . ?
O5 Ni1 N1 93.04(5) . . ?
O6 Ni1 N1 88.91(5) . . ?
O4 Ni1 N1 94.61(6) . 7_575 ?
O5 Ni1 N1 93.04(5) 7_575 7_575 ?
O5 Ni1 N1 173.02(5) . 7_575 ?
O6 Ni1 N1 88.91(5) . 7_575 ?
N1 Ni1 N1 80.05(7) . 7_575 ?
O3A P1A O1A 112.5(3) . . ?
O3A P1A O2A 111.4(5) . . ?
O1A P1A O2A 107.2(4) . . ?
O3A P1A C1A 113.7(4) . . ?
O1A P1A C1A 109.5(4) . . ?
O2A P1A C1A 101.8(3) . . ?
P1A O2A H2A 117(3) . . ?
C1A C1A P1A 115.3(3) 5_567 . ?
C1A C1A H1A1 108.4 5_567 . ?
P1A C1A H1A1 108.4 . . ?
C1A C1A H1A2 108.4 5_567 . ?
P1A C1A H1A2 108.4 . . ?
H1A1 C1A H1A2 107.5 . . ?
O1B P1B O2B 114.7(3) . . ?
O1B P1B O3B 111.9(3) . . ?
O2B P1B O3B 109.0(5) . . ?
O1B P1B C1B 112.3(5) . . ?
O2B P1B C1B 102.8(3) . . ?
O3B P1B C1B 105.4(3) . . ?
O1B P1B H3B 93.7(18) . . ?
O2B P1B H3B 98(2) . . ?
O3B P1B H3B 29.5(9) . . ?
C1B P1B H3B 134.8(10) . . ?
P1B O3B H3B 77(4) . . ?
C1B C1B P1B 115.4(3) 5_567 . ?
C1B C1B H1B1 108.4 5_567 . ?
P1B C1B H1B1 108.4 . . ?
C1B C1B H1B2 108.4 5_567 . ?
P1B C1B H1B2 108.4 . . ?
H1B1 C1B H1B2 107.5 . . ?
Ni1 O4 H4A 121.2(15) . . ?
Ni1 O5 H5A 124.8(16) . . ?
Ni1 O5 H5B 124.0(15) . . ?
H5A O5 H5B 111(2) . . ?
Ni1 O6 H6O 118.4(14) . . ?
C2 N1 C6 118.22(14) . . ?
C2 N1 Ni1 129.27(12) . . ?
C6 N1 Ni1 112.41(9) . . ?
N1 C2 C3 122.35(19) . . ?
N1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C4 C3 C2 119.71(18) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 119.87(18) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 116.63(18) . . ?
C6 C5 C7 118.81(19) . . ?
C4 C5 C7 124.56(18) . . ?
N1 C6 C5 123.20(15) . . ?
N1 C6 C6 117.11(8) . 7_575 ?
C5 C6 C6 119.66(11) . 7_575 ?
C7 C7 C5 121.50(12) 7_575 . ?
C7 C7 H7 119.3 7_575 . ?
C5 C7 H7 119.3 . . ?

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
O3A P1A C1A C1A -170.9(4) . . . 5_567 ?
O1A P1A C1A C1A 62.3(4) . . . 5_567 ?
O2A P1A C1A C1A -51.0(6) . . . 5_567 ?
O1B P1B C1B C1B 175.2(3) . . . 5_567 ?
O2B P1B C1B C1B 51.5(5) . . . 5_567 ?
O3B P1B C1B C1B -62.7(4) . . . 5_567 ?
C6 N1 C2 C3 1.1(3) . . . . ?
Ni1 N1 C2 C3 -174.93(13) . . . . ?
N1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C3 C4 C5 C7 -178.82(19) . . . . ?
C2 N1 C6 C5 -1.8(2) . . . . ?
Ni1 N1 C6 C5 174.93(12) . . . . ?
C2 N1 C6 C6 176.43(11) . . . 7_575 ?
Ni1 N1 C6 C6 -6.90(10) . . . 7_575 ?
C4 C5 C6 N1 1.0(2) . . . . ?
C7 C5 C6 N1 -179.75(16) . . . . ?
C4 C5 C6 C6 -177.09(13) . . . 7_575 ?
C7 C5 C6 C6 2.1(2) . . . 7_575 ?
C6 C5 C7 C7 -2.2(2) . . . 7_575 ?
C4 C5 C7 C7 176.98(15) . . . 7_575 ?

_refine_diff_density_max         0.483
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.087

_shelxl_version_number           2014/6

