# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 696828'
_audit_update_record             
;
2008-07-29 deposited with the CCDC.
2015-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H16 Co N O5 P'
_chemical_formula_sum            'C9 H16 Co N O5 P'
_chemical_formula_weight         308.13

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Hexagonal
_symmetry_space_group_name_H-M   'P 6(3) '
_symmetry_space_group_name_Hall  'P 6c '

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

_cell_length_a                   18.3143(10)
_cell_length_b                   18.3143(10)
_cell_length_c                   6.1688(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     1791.9(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    4180
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Prism
_exptl_crystal_colour            Pink
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             954
_exptl_absorpt_coefficient_mu    1.579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      291(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  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14116
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         27.47
_reflns_number_total             2188
_reflns_number_gt                2043
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_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)+(0.1087P)²+1.1720P] where P=(Fo²+2Fc²)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2188
_refine_ls_number_parameters     155
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1524
_refine_ls_wR_factor_gt          0.1414
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.032
_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
Co1 Co 0.07214(4) 0.83065(4) 0.69758(15) 0.0175(2) Uani 1 1 d . . .
P1 P 0.02202(7) 0.77939(7) 0.2186(3) 0.0171(3) Uani 1 1 d . . .
O1 O 0.0425(2) 0.8491(2) 0.3861(7) 0.0209(8) Uani 1 1 d . . .
O2 O 0.0830(2) 0.8119(3) 0.0257(8) 0.0234(9) Uani 1 1 d . . .
O3 O -0.0697(2) 0.7345(2) 0.1504(6) 0.0210(8) Uani 1 1 d . . .
O1W O -0.0541(2) 0.7211(2) 0.7198(8) 0.0219(8) Uani 1 1 d . . .
H4A H -0.0891 0.7338 0.6247 0.026 Uiso 1 1 d R . .
H4B H -0.0705 0.7218 0.8588 0.026 Uiso 1 1 d R . .
O2W O 0.0208(3) 0.9093(3) 0.7911(9) 0.0322(11) Uani 1 1 d . . .
H5B H -0.0264 0.8773 0.8516 0.039 Uiso 1 1 d R . .
H5A H 0.0512 0.9565 0.8837 0.039 Uiso 1 1 d R . .
N1 N 0.1071(3) 0.7448(3) 0.5268(8) 0.0196(9) Uani 1 1 d . . .
H1C H 0.1508 0.7726 0.4710 0.023 Uiso 1 1 d R . .
C1 C 0.0419(4) 0.7026(4) 0.3585(10) 0.0226(11) Uani 1 1 d . . .
H1A H -0.0099 0.6595 0.4248 0.027 Uiso 1 1 calc R . .
H1B H 0.0603 0.6755 0.2545 0.027 Uiso 1 1 calc R . .
C2 C 0.1237(4) 0.6866(3) 0.6591(11) 0.0256(13) Uani 1 1 d . . .
H2 H 0.0766 0.6582 0.7610 0.031 Uiso 1 1 calc R . .
C3 C 0.2034(5) 0.7380(5) 0.7945(13) 0.0400(16) Uani 1 1 d . . .
H3A H 0.2512 0.7666 0.7000 0.060 Uiso 1 1 calc R . .
H3B H 0.2115 0.7010 0.8890 0.060 Uiso 1 1 calc R . .
H3C H 0.1976 0.7787 0.8794 0.060 Uiso 1 1 calc R . .
C4 C 0.1280(4) 0.6184(4) 0.5306(11) 0.0267(12) Uani 1 1 d . . .
C5 C 0.1798(5) 0.6387(4) 0.3473(15) 0.0416(18) Uani 1 1 d . . .
H5 H 0.2127 0.6950 0.3071 0.050 Uiso 1 1 calc R . .
C6 C 0.1832(5) 0.5773(4) 0.2249(17) 0.0469(19) Uani 1 1 d . . .
H6 H 0.2164 0.5922 0.1008 0.056 Uiso 1 1 calc R . .
C7 C 0.1374(5) 0.4941(5) 0.2868(16) 0.046(2) Uani 1 1 d . . .
H7 H 0.1404 0.4528 0.2064 0.055 Uiso 1 1 calc R . .
C8 C 0.0871(4) 0.4724(4) 0.4677(14) 0.0399(18) Uani 1 1 d . . .
H8 H 0.0559 0.4161 0.5095 0.048 Uiso 1 1 calc R . .
C9 C 0.0826(4) 0.5343(4) 0.5888(13) 0.0349(15) Uani 1 1 d . . .
H9 H 0.0484 0.5188 0.7113 0.042 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
Co1 O1 2.070(4) . ?
Co1 O2 2.079(5) 1_556 ?
Co1 O3 2.101(3) 6_665 ?
Co1 O2W 2.156(4) . ?
Co1 O1W 2.180(3) . ?
Co1 N1 2.235(5) . ?
P1 O3 1.514(4) . ?
P1 O2 1.534(5) . ?
P1 O1 1.536(4) . ?
P1 C1 1.834(6) . ?
O2 Co1 2.079(5) 1_554 ?
O3 Co1 2.101(3) 5_454 ?
O1W H4A 0.9790 . ?
O1W H4B 0.9111 . ?
O2W H5B 0.8499 . ?
O2W H5A 0.9496 . ?
N1 C1 1.476(7) . ?
N1 C2 1.490(7) . ?
N1 H1C 0.7823 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C4 1.515(8) . ?
C2 C3 1.530(9) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C9 1.382(8) . ?
C4 C5 1.401(10) . ?
C5 C6 1.382(11) . ?
C5 H5 0.9300 . ?
C6 C7 1.375(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.373(11) . ?
C7 H7 0.9300 . ?
C8 C9 1.395(10) . ?
C8 H8 0.9300 . ?
C9 H9 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 Co1 O2 170.13(15) . 1_556 ?
O1 Co1 O3 89.23(15) . 6_665 ?
O2 Co1 O3 97.35(15) 1_556 6_665 ?
O1 Co1 O2W 84.35(19) . . ?
O2 Co1 O2W 87.67(19) 1_556 . ?
O3 Co1 O2W 95.63(15) 6_665 . ?
O1 Co1 O1W 87.97(17) . . ?
O2 Co1 O1W 86.07(17) 1_556 . ?
O3 Co1 O1W 174.37(16) 6_665 . ?
O2W Co1 O1W 88.96(15) . . ?
O1 Co1 N1 82.42(17) . . ?
O2 Co1 N1 104.95(18) 1_556 . ?
O3 Co1 N1 88.99(15) 6_665 . ?
O2W Co1 N1 165.93(19) . . ?
O1W Co1 N1 85.80(15) . . ?
O3 P1 O2 112.9(2) . . ?
O3 P1 O1 112.5(2) . . ?
O2 P1 O1 111.8(2) . . ?
O3 P1 C1 107.8(2) . . ?
O2 P1 C1 106.1(2) . . ?
O1 P1 C1 105.1(2) . . ?
P1 O1 Co1 117.6(2) . . ?
P1 O2 Co1 135.1(2) . 1_554 ?
P1 O3 Co1 133.7(2) . 5_454 ?
Co1 O1W H4A 105.2 . . ?
Co1 O1W H4B 104.6 . . ?
H4A O1W H4B 107.5 . . ?
Co1 O2W H5B 106.9 . . ?
Co1 O2W H5A 121.0 . . ?
H5B O2W H5A 107.1 . . ?
C1 N1 C2 114.3(4) . . ?
C1 N1 Co1 105.0(3) . . ?
C2 N1 Co1 118.6(4) . . ?
C1 N1 H1C 109.2 . . ?
C2 N1 H1C 101.4 . . ?
Co1 N1 H1C 108.0 . . ?
N1 C1 P1 110.4(4) . . ?
N1 C1 H1A 109.6 . . ?
P1 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
P1 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
N1 C2 C4 114.7(5) . . ?
N1 C2 C3 109.4(5) . . ?
C4 C2 C3 111.5(5) . . ?
N1 C2 H2 107.0 . . ?
C4 C2 H2 107.0 . . ?
C3 C2 H2 107.0 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C9 C4 C5 117.1(6) . . ?
C9 C4 C2 122.2(6) . . ?
C5 C4 C2 120.7(5) . . ?
C6 C5 C4 121.6(6) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C7 C6 C5 119.9(8) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C6 119.7(7) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 120.2(6) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C4 C9 C8 121.3(7) . . ?
C4 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.850
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.186
####################################################################### 
# 
# 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_co
_database_code_depnum_ccdc_archive 'CCDC 696829'
_audit_update_record             
;
2008-07-29 deposited with the CCDC.
2015-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H16 Co N O5 P'
_chemical_formula_sum            'C9 H16 Co N O5 P'
_chemical_formula_weight         308.13

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Hexagonal
_symmetry_space_group_name_H-M   'P 6(3) '
_symmetry_space_group_name_Hall  'P 6c '

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

_cell_length_a                   18.288(8)
_cell_length_b                   18.288(8)
_cell_length_c                   6.168(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     1786.5(16)
_cell_formula_units_Z            6
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    4180
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      27.48

_exptl_crystal_description       prism
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             954
_exptl_absorpt_coefficient_mu    1.584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      291(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  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12569
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_sigmaI/netI    0.0546
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2293
_reflns_number_gt                2002
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_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)+(0.0706P)²+1.1945P] where P=(Fo²+2Fc²)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2293
_refine_ls_number_parameters     154
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1260
_refine_ls_wR_factor_gt          0.1233
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.054
_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
Co1 Co 0.24155(4) 0.16931(4) 0.68866(13) 0.0323(2) Uani 1 1 d . . .
P1 P 0.24302(8) 0.22091(7) 0.2119(3) 0.0310(3) Uani 1 1 d . . .
O1 O 0.1934(2) 0.1516(2) 0.3769(7) 0.0362(9) Uani 1 1 d . . .
O2 O 0.2707(2) 0.1882(2) 0.0175(6) 0.0313(8) Uani 1 1 d . . .
O3 O 0.1955(2) 0.2658(2) 0.1392(6) 0.0287(8) Uani 1 1 d . . .
O1W O 0.2251(2) 0.2783(2) 0.7150(7) 0.0298(7) Uani 1 1 d . . .
H4A H 0.1770 0.2682 0.6264 0.036 Uiso 1 1 d R . .
H4B H 0.2033 0.2735 0.8612 0.036 Uiso 1 1 d R . .
O2W O 0.1114(2) 0.0910(2) 0.7836(7) 0.0310(8) Uani 1 1 d . . .
H5B H 0.1054 0.0981 0.9172 0.037 Uiso 1 1 d R . .
H5A H 0.0788 0.1068 0.6974 0.037 Uiso 1 1 d R . .
N1 N 0.3632(3) 0.2552(3) 0.5179(8) 0.0348(11) Uani 1 1 d . . .
H1C H 0.3786 0.2215 0.4458 0.042 Uiso 1 1 calc R . .
C1 C 0.3399(3) 0.2986(3) 0.3507(10) 0.0357(13) Uani 1 1 d . . .
H1A H 0.3853 0.3264 0.2464 0.043 Uiso 1 1 calc R . .
H1B H 0.3309 0.3413 0.4188 0.043 Uiso 1 1 calc R . .
C2 C 0.4370(3) 0.3140(3) 0.6554(9) 0.0346(12) Uani 1 1 d . . .
H2 H 0.4183 0.3422 0.7580 0.042 Uiso 1 1 calc R . .
C3 C 0.4656(3) 0.2610(4) 0.7840(10) 0.0355(13) Uani 1 1 d . . .
H3A H 0.4197 0.2217 0.8733 0.053 Uiso 1 1 d R . .
H3B H 0.5125 0.2979 0.8741 0.053 Uiso 1 1 d R . .
H3C H 0.4823 0.2307 0.6878 0.053 Uiso 1 1 d R . .
C4 C 0.5107(3) 0.3819(4) 0.5215(10) 0.0360(13) Uani 1 1 d . . .
C5 C 0.5404(4) 0.3613(4) 0.3380(11) 0.0442(16) Uani 1 1 d . . .
H5 H 0.5168 0.3050 0.2967 0.053 Uiso 1 1 calc R . .
C6 C 0.6047(3) 0.4235(4) 0.2165(12) 0.0436(14) Uani 1 1 d . . .
H6 H 0.6232 0.4089 0.0919 0.052 Uiso 1 1 calc R . .
C7 C 0.6415(4) 0.5062(4) 0.2773(11) 0.0460(17) Uani 1 1 d . . .
H7 H 0.6847 0.5482 0.1948 0.055 Uiso 1 1 calc R . .
C8 C 0.6140(3) 0.5262(3) 0.4601(11) 0.0376(14) Uani 1 1 d . . .
H8 H 0.6409 0.5821 0.5062 0.045 Uiso 1 1 calc R . .
C9 C 0.5476(3) 0.4661(3) 0.5789(10) 0.0322(11) Uani 1 1 d . . .
H9 H 0.5274 0.4819 0.6977 0.039 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
Co1 O1 2.072(4) . ?
Co1 O2 2.082(4) 1_556 ?
Co1 O3 2.090(4) 5 ?
Co1 O2W 2.156(4) . ?
Co1 O1W 2.166(3) . ?
Co1 N1 2.243(5) . ?
P1 O1 1.522(4) . ?
P1 O3 1.532(4) . ?
P1 O2 1.535(4) . ?
P1 C1 1.836(5) . ?
O2 Co1 2.082(4) 1_554 ?
O3 Co1 2.090(4) 6_554 ?
O1W H4A 0.9710 . ?
O1W H4B 0.9725 . ?
O2W H5B 0.8500 . ?
O2W H5A 0.9469 . ?
N1 C1 1.489(8) . ?
N1 C2 1.498(6) . ?
N1 H1C 0.9100 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.532(8) . ?
C2 C4 1.539(8) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9599 . ?
C3 H3B 0.9602 . ?
C3 H3C 0.9602 . ?
C4 C9 1.383(8) . ?
C4 C5 1.386(9) . ?
C5 C6 1.379(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.366(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.356(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.374(8) . ?
C8 H8 0.9300 . ?
C9 H9 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 Co1 O2 169.69(16) . 1_556 ?
O1 Co1 O3 89.23(15) . 5 ?
O2 Co1 O3 97.94(14) 1_556 5 ?
O1 Co1 O2W 84.64(16) . . ?
O2 Co1 O2W 87.24(15) 1_556 . ?
O3 Co1 O2W 96.09(14) 5 . ?
O1 Co1 O1W 88.28(17) . . ?
O2 Co1 O1W 85.19(16) 1_556 . ?
O3 Co1 O1W 174.43(14) 5 . ?
O2W Co1 O1W 88.64(13) . . ?
O1 Co1 N1 82.48(17) . . ?
O2 Co1 N1 105.01(16) 1_556 . ?
O3 Co1 N1 88.38(17) 5 . ?
O2W Co1 N1 166.30(16) . . ?
O1W Co1 N1 86.35(16) . . ?
O1 P1 O3 112.4(2) . . ?
O1 P1 O2 111.9(2) . . ?
O3 P1 O2 111.5(2) . . ?
O1 P1 C1 106.0(2) . . ?
O3 P1 C1 107.9(2) . . ?
O2 P1 C1 106.7(2) . . ?
P1 O1 Co1 117.4(2) . . ?
P1 O2 Co1 136.0(2) . 1_554 ?
P1 O3 Co1 133.2(2) . 6_554 ?
Co1 O1W H4A 108.2 . . ?
Co1 O1W H4B 103.1 . . ?
H4A O1W H4B 102.2 . . ?
Co1 O2W H5B 110.3 . . ?
Co1 O2W H5A 107.4 . . ?
H5B O2W H5A 110.3 . . ?
C1 N1 C2 113.9(4) . . ?
C1 N1 Co1 104.5(3) . . ?
C2 N1 Co1 117.3(4) . . ?
C1 N1 H1C 106.8 . . ?
C2 N1 H1C 106.8 . . ?
Co1 N1 H1C 106.8 . . ?
N1 C1 P1 109.4(3) . . ?
N1 C1 H1A 109.8 . . ?
P1 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
P1 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
N1 C2 C3 108.0(4) . . ?
N1 C2 C4 112.8(5) . . ?
C3 C2 C4 110.5(5) . . ?
N1 C2 H2 108.5 . . ?
C3 C2 H2 108.5 . . ?
C4 C2 H2 108.5 . . ?
C2 C3 H3A 109.0 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 110.7 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.4 . . ?
C9 C4 C5 118.2(5) . . ?
C9 C4 C2 120.2(6) . . ?
C5 C4 C2 121.5(5) . . ?
C6 C5 C4 120.5(5) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C7 C6 C5 120.6(6) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C8 C7 C6 118.9(6) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C7 C8 C9 121.8(5) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C8 C9 C4 119.9(6) . . ?
C8 C9 H9 120.1 . . ?
C4 C9 H9 120.1 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.086
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 696830'
_audit_update_record             
;
2008-07-29 deposited with the CCDC.
2015-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H16 N Ni O5 P'
_chemical_formula_sum            'C9 H16 N Ni O5 P'
_chemical_formula_weight         307.91

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'

_symmetry_cell_setting           Hexagonal
_symmetry_space_group_name_H-M   'P 6(3) '
_symmetry_space_group_name_Hall  'P 6c '

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

_cell_length_a                   18.0812(15)
_cell_length_b                   18.0812(15)
_cell_length_c                   6.1296(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     1735.5(3)
_cell_formula_units_Z            6
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    5251
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    1.824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      291(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  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13930
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2652
_reflns_number_gt                2521
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_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)+(0.0695P)²+0.5001P] where P=(Fo²+2Fc²)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(1)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2652
_refine_ls_number_parameters     155
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.1036
_refine_ls_wR_factor_gt          0.0818
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
Ni1 Ni 0.93060(2) 0.17084(2) 0.30375(9) 0.00804(13) Uani 1 1 d . . .
P1 P 0.97834(5) 0.22003(5) 0.78200(16) 0.00846(18) Uani 1 1 d . . .
O1 O 0.95808(15) 0.14946(15) 0.6142(4) 0.0100(5) Uani 1 1 d . . .
O2 O 0.91645(15) 0.18775(16) 0.9748(4) 0.0118(5) Uani 1 1 d . . .
O3 O 1.07160(15) 0.26595(15) 0.8509(4) 0.0109(5) Uani 1 1 d . . .
O1W O 1.05370(13) 0.27773(13) 0.2812(5) 0.0108(5) Uani 1 1 d . . .
H4A H 1.0887 0.2650 0.3762 0.013 Uiso 1 1 d R . .
H4B H 1.0701 0.2770 0.1421 0.013 Uiso 1 1 d R . .
O2W O 0.97799(16) 0.09203(15) 0.2117(4) 0.0133(5) Uani 1 1 d . . .
H5B H 1.0252 0.1240 0.1512 0.016 Uiso 1 1 d R . .
H5A H 0.9475 0.0449 0.1192 0.016 Uiso 1 1 d R . .
N1 N 0.89329(19) 0.25333(18) 0.4639(5) 0.0108(6) Uani 1 1 d . . .
H1C H 0.8495 0.2255 0.5198 0.013 Uiso 1 1 d R . .
C1 C 0.9583(2) 0.2967(2) 0.6376(6) 0.0108(7) Uani 1 1 d . . .
H1A H 0.9383 0.3238 0.7400 0.013 Uiso 1 1 calc R . .
H1B H 1.0110 0.3408 0.5731 0.013 Uiso 1 1 calc R . .
C2 C 0.8777(2) 0.3123(2) 0.3276(7) 0.0140(7) Uani 1 1 d . . .
H2 H 0.9253 0.3408 0.2250 0.017 Uiso 1 1 calc R . .
C3 C 0.7963(3) 0.2596(3) 0.1946(7) 0.0190(8) Uani 1 1 d . . .
H3A H 0.7483 0.2319 0.2914 0.029 Uiso 1 1 calc R . .
H3B H 0.8014 0.2174 0.1116 0.029 Uiso 1 1 calc R . .
H3C H 0.7881 0.2965 0.0973 0.029 Uiso 1 1 calc R . .
C4 C 0.8724(2) 0.3814(2) 0.4582(6) 0.0140(7) Uani 1 1 d . . .
C5 C 0.8201(3) 0.3602(3) 0.6428(8) 0.0206(8) Uani 1 1 d . . .
H5 H 0.7871 0.3032 0.6834 0.025 Uiso 1 1 calc R . .
C6 C 0.8167(3) 0.4225(3) 0.7658(8) 0.0243(9) Uani 1 1 d . . .
H6 H 0.7828 0.4074 0.8902 0.029 Uiso 1 1 calc R . .
C7 C 0.8640(3) 0.5076(3) 0.7039(7) 0.0209(8) Uani 1 1 d . . .
H7 H 0.8619 0.5497 0.7864 0.025 Uiso 1 1 calc R . .
C8 C 0.9140(3) 0.5292(2) 0.5195(7) 0.0202(8) Uani 1 1 d . . .
H8 H 0.9452 0.5860 0.4765 0.024 Uiso 1 1 calc R . .
C9 C 0.9181(2) 0.4663(2) 0.3961(7) 0.0189(8) Uani 1 1 d . . .
H9 H 0.9519 0.4816 0.2714 0.023 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
Ni1 O1 2.052(2) . ?
Ni1 O2 2.074(3) 1_554 ?
Ni1 O2W 2.075(2) . ?
Ni1 O3 2.087(2) 6_544 ?
Ni1 O1W 2.099(2) . ?
Ni1 N1 2.156(3) . ?
P1 O3 1.520(2) . ?
P1 O2 1.528(3) . ?
P1 O1 1.534(3) . ?
P1 C1 1.828(3) . ?
O2 Ni1 2.074(3) 1_556 ?
O3 Ni1 2.087(2) 5_665 ?
O1W H4A 0.9687 . ?
O1W H4B 0.9047 . ?
O2W H5B 0.8402 . ?
O2W H5A 0.9397 . ?
N1 C1 1.485(5) . ?
N1 C2 1.488(4) . ?
N1 H1C 0.7733 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C4 1.526(5) . ?
C2 C3 1.528(5) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C9 1.384(5) . ?
C4 C5 1.400(6) . ?
C5 C6 1.382(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.388(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.376(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.398(5) . ?
C8 H8 0.9300 . ?
C9 H9 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 Ni1 O2 171.36(10) . 1_554 ?
O1 Ni1 O2W 84.30(11) . . ?
O2 Ni1 O2W 87.74(11) 1_554 . ?
O1 Ni1 O3 88.27(9) . 6_544 ?
O2 Ni1 O3 95.79(9) 1_554 6_544 ?
O2W Ni1 O3 95.07(10) . 6_544 ?
O1 Ni1 O1W 89.39(11) . . ?
O2 Ni1 O1W 87.27(11) 1_554 . ?
O2W Ni1 O1W 90.14(9) . . ?
O3 Ni1 O1W 174.05(10) 6_544 . ?
O1 Ni1 N1 84.09(11) . . ?
O2 Ni1 N1 103.68(11) 1_554 . ?
O2W Ni1 N1 168.06(11) . . ?
O3 Ni1 N1 87.32(10) 6_544 . ?
O1W Ni1 N1 87.00(10) . . ?
O3 P1 O2 113.23(14) . . ?
O3 P1 O1 112.27(13) . . ?
O2 P1 O1 112.08(14) . . ?
O3 P1 C1 107.87(15) . . ?
O2 P1 C1 106.19(15) . . ?
O1 P1 C1 104.53(15) . . ?
P1 O1 Ni1 116.41(14) . . ?
P1 O2 Ni1 133.40(15) . 1_556 ?
P1 O3 Ni1 133.04(15) . 5_665 ?
Ni1 O1W H4A 105.1 . . ?
Ni1 O1W H4B 104.7 . . ?
H4A O1W H4B 107.8 . . ?
Ni1 O2W H5B 105.9 . . ?
Ni1 O2W H5A 122.1 . . ?
H5B O2W H5A 106.9 . . ?
C1 N1 C2 114.0(3) . . ?
C1 N1 Ni1 104.7(2) . . ?
C2 N1 Ni1 118.5(2) . . ?
C1 N1 H1C 107.9 . . ?
C2 N1 H1C 102.4 . . ?
Ni1 N1 H1C 108.9 . . ?
N1 C1 P1 110.5(2) . . ?
N1 C1 H1A 109.5 . . ?
P1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
P1 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
N1 C2 C4 113.8(3) . . ?
N1 C2 C3 108.8(3) . . ?
C4 C2 C3 110.8(3) . . ?
N1 C2 H2 107.7 . . ?
C4 C2 H2 107.7 . . ?
C3 C2 H2 107.7 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C9 C4 C5 118.2(4) . . ?
C9 C4 C2 121.1(4) . . ?
C5 C4 C2 120.6(3) . . ?
C6 C5 C4 121.1(4) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 120.1(4) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 119.5(4) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 120.5(4) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C4 C9 C8 120.5(4) . . ?
C4 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.950
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.189


####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1060995'
_audit_update_record             
;
2015-04-22 deposited with the CCDC.
2015-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H16 N Ni O5 P'
_chemical_formula_sum            'C9 H16 N Ni O5 P'
_chemical_formula_weight         307.91

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'
Ni Ni 0.3393 1.1124 '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      hexagonal
_space_group_IT_number           173
_space_group_name_H-M_alt        'P 63'
_space_group_name_Hall           'P 6c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, z+1/2'

_cell_length_a                   18.1621(6)
_cell_length_b                   18.1621(6)
_cell_length_c                   6.168(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1762(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    471
_cell_measurement_theta_min      2.242
_cell_measurement_theta_max      21.151

_exptl_crystal_description       niddle-like
_exptl_crystal_colour            'light green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.796
_shelx_estimated_absorpt_T_min   0.467
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   'SADABS(Bruker, 2000)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4903
_diffrn_reflns_av_unetI/netI     0.1264
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.243
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2188
_reflns_number_gt                1479
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.995

_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       'SMART (Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.05(4)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2188
_refine_ls_number_parameters     156
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.0736
_refine_ls_wR_factor_gt          0.0632
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_restrained_S_all      0.939
_refine_ls_shift/su_max          0.002
_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 0.76022(6) 0.82914(5) 0.06333(19) 0.0140(2) Uani 1 1 d . . . . .
P1 P 0.75872(13) 0.77979(12) 0.5404(5) 0.0133(5) Uani 1 1 d . . . . .
C1 C 0.6622(5) 0.7036(5) 0.3989(14) 0.018(2) Uani 1 1 d . . . . .
H1A H 0.6703 0.6592 0.3359 0.022 Uiso 1 1 calc R U . . .
H1B H 0.6155 0.6773 0.5012 0.022 Uiso 1 1 calc R U . . .
C2 C 0.5659(5) 0.6886(5) 0.088(2) 0.026(3) Uani 1 1 d . . . . .
H2 H 0.5843 0.6595 -0.0136 0.031 Uiso 1 1 calc R U . . .
C3 C 0.5387(6) 0.7410(6) -0.0435(13) 0.032(3) Uani 1 1 d . . . . .
H3A H 0.5213 0.7711 0.0522 0.048 Uiso 1 1 calc R U . . .
H3B H 0.4920 0.7042 -0.1357 0.048 Uiso 1 1 calc R U . . .
H3C H 0.5855 0.7809 -0.1309 0.048 Uiso 1 1 calc R U . . .
C4 C 0.4919(6) 0.6203(6) 0.2205(16) 0.022(2) Uani 1 1 d . . . . .
C5 C 0.4604(6) 0.6404(6) 0.4040(17) 0.032(3) Uani 1 1 d . . . . .
H5 H 0.4841 0.6969 0.4458 0.038 Uiso 1 1 calc R U . . .
C6 C 0.3952(5) 0.5783(6) 0.524(2) 0.041(3) Uani 1 1 d . . . . .
H6 H 0.3763 0.5930 0.6479 0.050 Uiso 1 1 calc R U . . .
C7 C 0.3580(6) 0.4945(6) 0.4620(16) 0.035(3) Uani 1 1 d . . . . .
H7 H 0.3142 0.4522 0.5434 0.042 Uiso 1 1 calc R U . . .
C8 C 0.3866(6) 0.4745(7) 0.2772(18) 0.034(3) Uani 1 1 d . . . . .
H8 H 0.3605 0.4182 0.2317 0.041 Uiso 1 1 calc R U . . .
C9 C 0.4535(6) 0.5362(6) 0.1573(14) 0.027(3) Uani 1 1 d . . . . .
H9 H 0.4725 0.5210 0.0345 0.033 Uiso 1 1 calc R U . . .
N1 N 0.6411(4) 0.7464(4) 0.2259(11) 0.0143(18) Uani 1 1 d . . . . .
H1C H 0.6259 0.7798 0.2968 0.017 Uiso 1 1 d R U . . .
O1 O 0.8081(3) 0.8498(4) 0.3730(9) 0.0139(13) Uani 1 1 d . . . . .
O2 O 0.7292(4) 0.8116(4) 0.7337(8) 0.0186(16) Uani 1 1 d . . . . .
O3 O 0.8067(3) 0.7349(3) 0.6111(9) 0.0142(16) Uani 1 1 d . . . . .
O1W O 0.7765(3) 0.7231(3) 0.0412(13) 0.0177(13) Uani 1 1 d . . . . .
H1WA H 0.8165 0.7294 0.1245 0.021 Uiso 1 1 d R U . . .
H1WB H 0.7877 0.7176 -0.0895 0.021 Uiso 1 1 d R U . . .
O2W O 0.8861(3) 0.9086(3) -0.0281(8) 0.0235(16) Uani 1 1 d . . . . .
H2WA H 0.9068 0.8773 -0.0617 0.028 Uiso 1 1 d R U . . .
H2WB H 0.8952 0.9449 -0.1266 0.028 Uiso 1 1 d 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 O1 2.054(6) . ?
Ni1 O2W 2.080(6) . ?
Ni1 O3 2.089(5) 5_564 ?
Ni1 O2 2.092(6) 1_554 ?
Ni1 O1W 2.094(4) . ?
Ni1 N1 2.167(7) . ?
P1 O3 1.524(5) . ?
P1 O1 1.533(6) . ?
P1 O2 1.534(6) . ?
P1 C1 1.823(8) . ?
C1 N1 1.480(10) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 N1 1.503(11) . ?
C2 C3 1.508(12) . ?
C2 C4 1.531(13) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C9 1.381(12) . ?
C4 C5 1.396(13) . ?
C5 C6 1.374(12) . ?
C5 H5 0.9300 . ?
C6 C7 1.375(12) . ?
C6 H6 0.9300 . ?
C7 C8 1.375(13) . ?
C7 H7 0.9300 . ?
C8 C9 1.384(12) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
N1 H1C 0.8953 . ?
O2 Ni1 2.092(6) 1_556 ?
O3 Ni1 2.089(5) 6_655 ?
O1W H1WA 0.8495 . ?
O1W H1WB 0.8497 . ?
O2W H2WA 0.8503 . ?
O2W H2WB 0.8497 . ?

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 Ni1 O2W 84.7(2) . . ?
O1 Ni1 O3 88.1(2) . 5_564 ?
O2W Ni1 O3 94.6(2) . 5_564 ?
O1 Ni1 O2 171.5(2) . 1_554 ?
O2W Ni1 O2 87.8(2) . 1_554 ?
O3 Ni1 O2 96.3(2) 5_564 1_554 ?
O1 Ni1 O1W 89.3(3) . . ?
O2W Ni1 O1W 90.5(2) . . ?
O3 Ni1 O1W 174.1(3) 5_564 . ?
O2 Ni1 O1W 87.0(3) 1_554 . ?
O1 Ni1 N1 83.2(2) . . ?
O2W Ni1 N1 167.6(2) . . ?
O3 Ni1 N1 87.6(2) 5_564 . ?
O2 Ni1 N1 104.2(2) 1_554 . ?
O1W Ni1 N1 86.8(2) . . ?
O3 P1 O1 112.5(3) . . ?
O3 P1 O2 112.3(4) . . ?
O1 P1 O2 112.4(3) . . ?
O3 P1 C1 108.7(3) . . ?
O1 P1 C1 104.4(4) . . ?
O2 P1 C1 105.9(4) . . ?
N1 C1 P1 110.5(6) . . ?
N1 C1 H1A 109.6 . . ?
P1 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
P1 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
N1 C2 C3 109.5(7) . . ?
N1 C2 C4 112.8(10) . . ?
C3 C2 C4 111.5(7) . . ?
N1 C2 H2 107.6 . . ?
C3 C2 H2 107.6 . . ?
C4 C2 H2 107.6 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C9 C4 C5 118.1(9) . . ?
C9 C4 C2 119.9(9) . . ?
C5 C4 C2 121.9(9) . . ?
C6 C5 C4 121.4(9) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 120.2(11) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C8 118.8(10) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C7 C8 C9 121.6(9) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C4 C9 C8 119.9(9) . . ?
C4 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C1 N1 C2 115.1(7) . . ?
C1 N1 Ni1 105.5(5) . . ?
C2 N1 Ni1 117.8(6) . . ?
C1 N1 H1C 104.6 . . ?
C2 N1 H1C 105.7 . . ?
Ni1 N1 H1C 107.2 . . ?
P1 O1 Ni1 117.1(3) . . ?
P1 O2 Ni1 134.0(3) . 1_556 ?
P1 O3 Ni1 133.3(3) . 6_655 ?
Ni1 O1W H1WA 109.9 . . ?
Ni1 O1W H1WB 108.8 . . ?
H1WA O1W H1WB 110.6 . . ?
Ni1 O2W H2WA 107.6 . . ?
Ni1 O2W H2WB 116.9 . . ?
H2WA O2W H2WB 111.5 . . ?

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 C1 N1 -146.9(6) . . . . ?
O1 P1 C1 N1 -26.6(7) . . . . ?
O2 P1 C1 N1 92.3(6) . . . . ?
N1 C2 C4 C9 -130.6(9) . . . . ?
C3 C2 C4 C9 105.8(10) . . . . ?
N1 C2 C4 C5 50.4(12) . . . . ?
C3 C2 C4 C5 -73.2(13) . . . . ?
C9 C4 C5 C6 2.4(15) . . . . ?
C2 C4 C5 C6 -178.6(9) . . . . ?
C4 C5 C6 C7 -1.6(16) . . . . ?
C5 C6 C7 C8 -0.6(16) . . . . ?
C6 C7 C8 C9 2.1(16) . . . . ?
C5 C4 C9 C8 -0.9(14) . . . . ?
C2 C4 C9 C8 180.0(9) . . . . ?
C7 C8 C9 C4 -1.3(16) . . . . ?
P1 C1 N1 C2 175.9(6) . . . . ?
P1 C1 N1 Ni1 44.3(6) . . . . ?
C3 C2 N1 C1 166.6(8) . . . . ?
C4 C2 N1 C1 41.8(10) . . . . ?
C3 C2 N1 Ni1 -67.9(9) . . . . ?
C4 C2 N1 Ni1 167.3(6) . . . . ?
O3 P1 O1 Ni1 111.1(4) . . . . ?
O2 P1 O1 Ni1 -120.9(3) . . . . ?
C1 P1 O1 Ni1 -6.6(5) . . . . ?
O3 P1 O2 Ni1 14.8(6) . . . 1_556 ?
O1 P1 O2 Ni1 -113.3(5) . . . 1_556 ?
C1 P1 O2 Ni1 133.3(5) . . . 1_556 ?
O1 P1 O3 Ni1 10.7(6) . . . 6_655 ?
O2 P1 O3 Ni1 -117.4(5) . . . 6_655 ?
C1 P1 O3 Ni1 125.8(5) . . . 6_655 ?

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
O2W H2WB O1 0.85 2.28 2.870(8) 126.3 5_564
O2W H2WA O1 0.85 1.95 2.796(8) 177.2 6_654
O1W H1WB O3 0.85 1.88 2.695(10) 161.6 1_554
O1W H1WA O2 0.85 1.96 2.775(8) 161.3 6_654
C3 H3C O2 0.96 2.52 3.327(11) 141.2 1_554
O2W H2WB O1 0.85 2.28 2.870(8) 126.3 5_564
O2W H2WA O1 0.85 1.95 2.796(8) 177.2 6_654
O1W H1WB O3 0.85 1.88 2.695(10) 161.6 1_554
O1W H1WA O2 0.85 1.96 2.775(8) 161.3 6_654
C3 H3C O2 0.96 2.52 3.327(11) 141.2 1_554
C3 H3C O2 0.96 2.52 3.327(11) 141.2 1_554
O1W H1WA O2 0.85 1.96 2.775(8) 161.3 6_654
O1W H1WB O3 0.85 1.88 2.695(10) 161.6 1_554
O2W H2WA O1 0.85 1.95 2.796(8) 177.2 6_654
O2W H2WB O1 0.85 2.28 2.870(8) 126.3 5_564

_refine_diff_density_max         0.658
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.105

_shelxl_version_number           2013-4

