# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1D
_database_code_depnum_ccdc_archive 'CCDC 1854500'
_audit_update_record             
;
2018-07-16 deposited with the CCDC.
2018-08-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H18 Co N2 O9 P'
_chemical_formula_weight         388.15

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'
Co Co 0.3494 0.9721 '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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   5.8605(4)
_cell_length_b                   13.6144(9)
_cell_length_c                   19.3605(14)
_cell_angle_alpha                90
_cell_angle_beta                 105.582(3)
_cell_angle_gamma                90
_cell_volume                     1487.95(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7955
_cell_measurement_theta_min      2.6476
_cell_measurement_theta_max      25.0391

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    1.308
_shelx_estimated_absorpt_T_min   0.880
_shelx_estimated_absorpt_T_max   0.914
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25325
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_av_R_equivalents  0.1350
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.648
_diffrn_reflns_theta_max         25.083
_diffrn_reflns_theta_full        25.083
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2621
_reflns_number_gt                2082
_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 Instrument Service vV6.2.3'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0259P)²+44.3609P] 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_number_reflns         2621
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1058
_refine_ls_R_factor_gt           0.0845
_refine_ls_wR_factor_ref         0.2057
_refine_ls_wR_factor_gt          0.1963
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
Co1 Co 0.5461(2) 0.85521(9) 0.90921(6) 0.0111(3) Uani 1 1 d . . . . .
P1 P 0.4562(5) 0.62617(18) 0.93334(13) 0.0200(6) Uani 1 1 d . . . . .
O1 O 0.6239(11) 0.7086(4) 0.9313(3) 0.0157(14) Uani 1 1 d . . . . .
H1 H 0.2603 0.6404 0.8811 0.019 Uiso 1 1 d R U . . .
O2 O 0.3736(12) 0.6197(5) 0.9999(4) 0.0242(16) Uani 1 1 d . . . . .
O3 O 0.567(2) 0.5285(5) 0.9189(5) 0.052(3) Uani 1 1 d . . . . .
H3 H 0.5661 0.4780 0.9446 0.063 Uiso 1 1 d R U . . .
O4 O 0.5720(11) 0.8409(5) 0.8068(3) 0.0166(14) Uani 1 1 d . . . . .
O5 O 0.9279(11) 0.8662(5) 0.9217(3) 0.0160(14) Uani 1 1 d . . . . .
O6 O 0.8102(12) 0.7807(6) 0.7456(4) 0.0277(17) Uani 1 1 d . . . . .
O7 O 1.1873(11) 0.8295(5) 0.8597(3) 0.0187(15) Uani 1 1 d . . . . .
O8 O 0.5351(11) 0.8742(4) 1.0151(3) 0.0169(14) Uani 1 1 d . . . . .
O9 O 0.4988(12) 0.9927(5) 1.0895(3) 0.0198(15) Uani 1 1 d . . . . .
C1 C 0.7750(15) 0.8181(7) 0.8002(5) 0.0144(19) Uani 1 1 d . . . . .
C2 C 0.9844(15) 0.8402(6) 0.8674(5) 0.0128(19) Uani 1 1 d . . . . .
C3 C 0.5096(16) 0.9615(7) 1.0304(5) 0.015(2) Uani 1 1 d . . . . .
N1 N 0.2058(13) 0.7874(5) 0.6994(4) 0.0125(16) Uani 1 1 d . . . . .
H1A H 0.0739 0.7776 0.7128 0.015 Uiso 1 1 calc R U . . .
H1B H 0.3233 0.7972 0.7388 0.015 Uiso 1 1 calc R U . . .
N2 N 0.0377(14) 0.7712(6) 0.5470(4) 0.0217(19) Uani 1 1 d . . . . .
H2A H 0.1706 0.7817 0.5342 0.026 Uiso 1 1 calc R U . . .
H2B H -0.0785 0.7611 0.5073 0.026 Uiso 1 1 calc R U . . .
C4 C 0.2584(16) 0.6971(7) 0.6619(5) 0.015(2) Uani 1 1 d . . . . .
H4 H 0.4100 0.7059 0.6503 0.018 Uiso 1 1 calc R U . . .
C5 C 0.0670(18) 0.6811(7) 0.5938(5) 0.021(2) Uani 1 1 d . . . . .
H5A H -0.0811 0.6666 0.6050 0.025 Uiso 1 1 calc R U . . .
H5B H 0.1074 0.6253 0.5682 0.025 Uiso 1 1 calc R U . . .
C6 C -0.0176(19) 0.8587(8) 0.5846(5) 0.025(2) Uani 1 1 d . . . . .
H6A H -0.1678 0.8491 0.5958 0.030 Uiso 1 1 calc R U . . .
H6B H -0.0328 0.9155 0.5535 0.030 Uiso 1 1 calc R U . . .
C7 C 0.1760(17) 0.8776(7) 0.6537(5) 0.018(2) Uani 1 1 d . . . . .
H7 H 0.3251 0.8908 0.6416 0.021 Uiso 1 1 calc R U . . .
C8 C 0.2783(19) 0.6100(7) 0.7131(6) 0.026(2) Uani 1 1 d . . . . .
H8A H 0.4003 0.6228 0.7563 0.038 Uiso 1 1 calc R U . . .
H8B H 0.3171 0.5518 0.6907 0.038 Uiso 1 1 calc R U . . .
H8C H 0.1300 0.6007 0.7244 0.038 Uiso 1 1 calc R U . . .
C9 C 0.1172(18) 0.9651(8) 0.6944(6) 0.025(2) Uani 1 1 d . . . . .
H9A H -0.0415 0.9586 0.6987 0.037 Uiso 1 1 calc R U . . .
H9B H 0.1300 1.0244 0.6689 0.037 Uiso 1 1 calc R U . . .
H9C H 0.2260 0.9675 0.7413 0.037 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
Co1 O4 2.038(6) . ?
Co1 O1 2.066(6) . ?
Co1 O8 2.084(6) . ?
Co1 O9 2.088(7) 3_677 ?
Co1 O7 2.093(6) 1_455 ?
Co1 O5 2.190(6) . ?
P1 O2 1.497(7) . ?
P1 O1 1.500(7) . ?
P1 O3 1.540(8) . ?
P1 H1 1.3240 . ?
O3 H3 0.8499 . ?
O4 C1 1.269(11) . ?
O5 C2 1.236(11) . ?
O6 C1 1.239(11) . ?
O7 C2 1.247(11) . ?
O7 Co1 2.093(6) 1_655 ?
O8 C3 1.243(11) . ?
O9 C3 1.240(11) . ?
O9 Co1 2.088(7) 3_677 ?
C1 C2 1.559(12) . ?
C3 C3 1.557(17) 3_677 ?
N1 C7 1.496(12) . ?
N1 C4 1.502(11) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N2 C6 1.478(13) . ?
N2 C5 1.507(13) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
C4 C5 1.500(13) . ?
C4 C8 1.529(13) . ?
C4 H4 0.9800 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.526(13) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C9 1.518(13) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

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 Co1 O1 92.2(3) . . ?
O4 Co1 O8 177.1(3) . . ?
O1 Co1 O8 88.9(2) . . ?
O4 Co1 O9 98.6(3) . 3_677 ?
O1 Co1 O9 167.7(3) . 3_677 ?
O8 Co1 O9 80.1(2) . 3_677 ?
O4 Co1 O7 82.3(2) . 1_455 ?
O1 Co1 O7 94.1(3) . 1_455 ?
O8 Co1 O7 100.3(3) . 1_455 ?
O9 Co1 O7 93.3(3) 3_677 1_455 ?
O4 Co1 O5 76.9(2) . . ?
O1 Co1 O5 83.1(2) . . ?
O8 Co1 O5 100.6(2) . . ?
O9 Co1 O5 93.4(3) 3_677 . ?
O7 Co1 O5 158.9(2) 1_455 . ?
O2 P1 O1 115.7(4) . . ?
O2 P1 O3 110.9(4) . . ?
O1 P1 O3 109.2(5) . . ?
O2 P1 H1 104.6 . . ?
O1 P1 H1 108.1 . . ?
O3 P1 H1 108.1 . . ?
P1 O1 Co1 128.2(4) . . ?
P1 O3 H3 121.4 . . ?
C1 O4 Co1 116.0(6) . . ?
C2 O5 Co1 112.7(6) . . ?
C2 O7 Co1 143.0(6) . 1_655 ?
C3 O8 Co1 113.0(6) . . ?
C3 O9 Co1 112.9(6) . 3_677 ?
O6 C1 O4 124.2(9) . . ?
O6 C1 C2 121.1(8) . . ?
O4 C1 C2 114.7(8) . . ?
O5 C2 O7 128.2(8) . . ?
O5 C2 C1 115.8(7) . . ?
O7 C2 C1 116.0(8) . . ?
O9 C3 O8 126.0(8) . . ?
O9 C3 C3 117.1(10) . 3_677 ?
O8 C3 C3 117.0(10) . 3_677 ?
C7 N1 C4 113.1(7) . . ?
C7 N1 H1A 109.0 . . ?
C4 N1 H1A 109.0 . . ?
C7 N1 H1B 109.0 . . ?
C4 N1 H1B 109.0 . . ?
H1A N1 H1B 107.8 . . ?
C6 N2 C5 111.4(7) . . ?
C6 N2 H2A 109.3 . . ?
C5 N2 H2A 109.3 . . ?
C6 N2 H2B 109.3 . . ?
C5 N2 H2B 109.3 . . ?
H2A N2 H2B 108.0 . . ?
C5 C4 N1 110.0(7) . . ?
C5 C4 C8 111.5(8) . . ?
N1 C4 C8 108.2(7) . . ?
C5 C4 H4 109.1 . . ?
N1 C4 H4 109.1 . . ?
C8 C4 H4 109.1 . . ?
C4 C5 N2 110.4(8) . . ?
C4 C5 H5A 109.6 . . ?
N2 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
N2 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
N2 C6 C7 111.0(8) . . ?
N2 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
N2 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
N1 C7 C9 110.1(7) . . ?
N1 C7 C6 108.8(8) . . ?
C9 C7 C6 111.6(8) . . ?
N1 C7 H7 108.8 . . ?
C9 C7 H7 108.8 . . ?
C6 C7 H7 108.8 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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
O2 P1 O1 Co1 -78.8(6) . . . . ?
O3 P1 O1 Co1 155.3(5) . . . . ?
Co1 O4 C1 O6 159.3(8) . . . . ?
Co1 O4 C1 C2 -20.3(10) . . . . ?
Co1 O5 C2 O7 -172.9(7) . . . . ?
Co1 O5 C2 C1 7.1(9) . . . . ?
Co1 O7 C2 O5 -10.1(17) 1_655 . . . ?
Co1 O7 C2 C1 170.0(7) 1_655 . . . ?
O6 C1 C2 O5 -171.4(9) . . . . ?
O4 C1 C2 O5 8.1(12) . . . . ?
O6 C1 C2 O7 8.5(13) . . . . ?
O4 C1 C2 O7 -171.9(8) . . . . ?
Co1 O9 C3 O8 -179.8(8) 3_677 . . . ?
Co1 O9 C3 C3 0.4(12) 3_677 . . 3_677 ?
Co1 O8 C3 O9 -179.6(8) . . . . ?
Co1 O8 C3 C3 0.2(12) . . . 3_677 ?
C7 N1 C4 C5 -56.6(10) . . . . ?
C7 N1 C4 C8 -178.5(7) . . . . ?
N1 C4 C5 N2 55.4(10) . . . . ?
C8 C4 C5 N2 175.4(8) . . . . ?
C6 N2 C5 C4 -57.7(10) . . . . ?
C5 N2 C6 C7 58.2(10) . . . . ?
C4 N1 C7 C9 178.5(8) . . . . ?
C4 N1 C7 C6 56.0(10) . . . . ?
N2 C6 C7 N1 -56.2(10) . . . . ?
N2 C6 C7 C9 -177.8(8) . . . . ?

_refine_diff_density_max         1.393
_refine_diff_density_min         -0.973
_refine_diff_density_rms         0.152

####################################################################### 
# 
# 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_2D
_database_code_depnum_ccdc_archive 'CCDC 1854501'
_audit_update_record             
;
2018-07-16 deposited with the CCDC.
2018-08-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H20 Co2 N2 O14 P2'
_chemical_formula_weight         572.08

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   15.3007(9)
_cell_length_b                   8.2832(5)
_cell_length_c                   16.2601(10)
_cell_angle_alpha                90
_cell_angle_beta                 113.487(2)
_cell_angle_gamma                90
_cell_volume                     1890.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9976
_cell_measurement_theta_min      2.5313
_cell_measurement_theta_max      28.3962

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.010
_exptl_crystal_F_000             1160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    2.002
_shelx_estimated_absorpt_T_min   0.690
_shelx_estimated_absorpt_T_max   0.753
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21039
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_av_R_equivalents  0.0799
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.531
_diffrn_reflns_theta_max         28.406
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4730
_reflns_number_gt                3761
_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 Instrument Service vV6.2.3'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  "SHELXL-2014/7 (Sheldrick, 2014)'"
_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)+(0.0278P)²+2.2937P] 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_number_reflns         4730
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0876
_refine_ls_wR_factor_gt          0.0810
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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
Co1 Co 0.66798(2) 0.56621(4) 0.64856(2) 0.00781(9) Uani 1 1 d . . . . .
Co2 Co 0.83255(2) 1.01135(4) 0.84509(2) 0.00777(9) Uani 1 1 d . . . . .
P1 P 0.87869(5) 0.69808(8) 0.73568(5) 0.00932(15) Uani 1 1 d . . . . .
H1 H 0.9131 0.5706 0.7679 0.011 Uiso 1 1 d R U . . .
P2 P 0.61444(5) 0.89063(9) 0.74422(5) 0.00975(15) Uani 1 1 d . . . . .
H2 H 0.5867 1.0235 0.7072 0.012 Uiso 1 1 d R U . . .
O1 O 0.78899(13) 0.6814(2) 0.65125(12) 0.0115(4) Uani 1 1 d . . . . .
O2 O 0.87495(13) 0.7999(2) 0.80984(12) 0.0133(4) Uani 1 1 d . . . . .
O3 O 0.96242(14) 0.7619(3) 0.71160(13) 0.0168(4) Uani 1 1 d . . . . .
H3A H 0.9733 0.7048 0.6732 0.020 Uiso 1 1 d R U . . .
O4 O 0.62140(13) 0.7792(2) 0.67506(13) 0.0146(4) Uani 1 1 d . . . . .
O5 O 0.70235(13) 0.9149(2) 0.82970(12) 0.0114(4) Uani 1 1 d . . . . .
O6 O 0.52855(14) 0.8319(3) 0.76602(14) 0.0212(5) Uani 1 1 d . . . . .
H6A H 0.5213 0.8776 0.8097 0.025 Uiso 1 1 d R U . . .
O7 O 0.73360(14) 0.3398(2) 0.63875(12) 0.0122(4) Uani 1 1 d . . . . .
O8 O 0.71340(14) 0.4687(2) 0.77965(12) 0.0134(4) Uani 1 1 d . . . . .
O9 O 0.77820(14) 0.2469(2) 0.86042(12) 0.0122(4) Uani 1 1 d . . . . .
O10 O 0.79682(14) 0.1170(2) 0.71818(12) 0.0132(4) Uani 1 1 d . . . . .
O11 O 0.60725(13) 0.5833(2) 0.50720(12) 0.0115(4) Uani 1 1 d . . . . .
O12 O 0.47092(13) 0.5444(2) 0.38726(12) 0.0121(4) Uani 1 1 d . . . . .
O13 O 0.88316(13) 0.9559(2) 0.98405(12) 0.0107(4) Uani 1 1 d . . . . .
O14 O 1.01999(13) 0.9065(2) 1.10199(12) 0.0114(4) Uani 1 1 d . . . . .
C1 C 0.76151(19) 0.2551(3) 0.70881(17) 0.0099(5) Uani 1 1 d . . . . .
C2 C 0.74914(18) 0.3304(3) 0.79018(17) 0.0091(5) Uani 1 1 d . . . . .
C3 C 0.52305(18) 0.5368(3) 0.46971(17) 0.0080(5) Uani 1 1 d . . . . .
C4 C 0.97157(19) 0.9609(3) 1.02467(17) 0.0086(5) Uani 1 1 d . . . . .
C5 C 0.5833(2) 0.1483(4) 0.4679(2) 0.0190(6) Uani 1 1 d . . . . .
H5A H 0.5884 0.2292 0.5118 0.029 Uiso 1 1 calc R U . . .
H5B H 0.5267 0.0856 0.4555 0.029 Uiso 1 1 calc R U . . .
H5C H 0.5801 0.1994 0.4138 0.029 Uiso 1 1 calc R U . . .
C6 C 0.66979(19) 0.0386(3) 0.50369(17) 0.0111(5) Uani 1 1 d . . . . .
H6 H 0.6771 -0.0029 0.5625 0.013 Uiso 1 1 calc R U . . .
C7 C 0.65967(19) -0.1016(3) 0.44132(17) 0.0109(5) Uani 1 1 d . . . . .
H7A H 0.6049 -0.1661 0.4363 0.013 Uiso 1 1 calc R U . . .
H7B H 0.6492 -0.0613 0.3821 0.013 Uiso 1 1 calc R U . . .
C8 C 0.83306(19) -0.1081(3) 0.48665(18) 0.0110(5) Uani 1 1 d . . . . .
H8A H 0.8275 -0.0687 0.4286 0.013 Uiso 1 1 calc R U . . .
H8B H 0.8889 -0.1768 0.5106 0.013 Uiso 1 1 calc R U . . .
C9 C 0.84514(19) 0.0334(3) 0.54918(17) 0.0105(5) Uani 1 1 d . . . . .
H9 H 0.8546 -0.0074 0.6087 0.013 Uiso 1 1 calc R U . . .
C10 C 0.9301(2) 0.1357(4) 0.5570(2) 0.0176(6) Uani 1 1 d . . . . .
H10A H 0.9220 0.1740 0.4987 0.026 Uiso 1 1 calc R U . . .
H10B H 0.9871 0.0720 0.5817 0.026 Uiso 1 1 calc R U . . .
H10C H 0.9351 0.2261 0.5956 0.026 Uiso 1 1 calc R U . . .
N1 N 0.75635(15) 0.1343(3) 0.51376(14) 0.0091(4) Uani 1 1 d . . . . .
H1A H 0.7626 0.2164 0.5510 0.011 Uiso 1 1 calc R U . . .
H1B H 0.7489 0.1750 0.4607 0.011 Uiso 1 1 calc R U . . .
N2 N 0.74703(15) -0.2039(3) 0.47555(15) 0.0111(5) Uani 1 1 d . . . . .
H2A H 0.7541 -0.2465 0.5281 0.013 Uiso 1 1 calc R U . . .
H2B H 0.7406 -0.2845 0.4374 0.013 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
Co1 O4 2.0130(19) . ?
Co1 O1 2.0679(18) . ?
Co1 O11 2.1129(18) . ?
Co1 O8 2.1211(19) . ?
Co1 O7 2.1628(19) . ?
Co1 O12 2.1702(19) 3_666 ?
Co2 O2 2.0282(19) . ?
Co2 O5 2.0669(19) . ?
Co2 O10 2.1033(18) 1_565 ?
Co2 O13 2.1264(18) . ?
Co2 O9 2.1740(19) 1_565 ?
Co2 O14 2.1786(19) 3_777 ?
P1 O2 1.4912(19) . ?
P1 O1 1.512(2) . ?
P1 O3 1.5728(19) . ?
P1 H1 1.2032 . ?
P2 O4 1.4908(19) . ?
P2 O5 1.514(2) . ?
P2 O6 1.569(2) . ?
P2 H2 1.2450 . ?
O3 H3A 0.8500 . ?
O6 H6A 0.8500 . ?
O7 C1 1.259(3) . ?
O8 C2 1.251(3) . ?
O9 C2 1.255(3) . ?
O9 Co2 2.1740(19) 1_545 ?
O10 C1 1.248(3) . ?
O10 Co2 2.1034(18) 1_545 ?
O11 C3 1.247(3) . ?
O12 C3 1.259(3) . ?
O12 Co1 2.1702(19) 3_666 ?
O13 C4 1.247(3) . ?
O14 C4 1.261(3) . ?
O14 Co2 2.1786(18) 3_777 ?
C1 C2 1.541(3) . ?
C3 C3 1.547(5) 3_666 ?
C4 C4 1.542(5) 3_777 ?
C5 C6 1.517(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 N1 1.496(3) . ?
C6 C7 1.508(4) . ?
C6 H6 0.9800 . ?
C7 N2 1.491(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N2 1.485(3) . ?
C8 C9 1.514(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N1 1.501(3) . ?
C9 C10 1.514(4) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?

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 Co1 O1 88.93(8) . . ?
O4 Co1 O11 97.73(8) . . ?
O1 Co1 O11 89.66(7) . . ?
O4 Co1 O8 96.95(7) . . ?
O1 Co1 O8 102.86(8) . . ?
O11 Co1 O8 160.85(8) . . ?
O4 Co1 O7 171.97(8) . . ?
O1 Co1 O7 87.92(7) . . ?
O11 Co1 O7 89.64(7) . . ?
O8 Co1 O7 76.58(7) . . ?
O4 Co1 O12 92.02(8) . 3_666 ?
O1 Co1 O12 166.76(7) . 3_666 ?
O11 Co1 O12 77.13(7) . 3_666 ?
O8 Co1 O12 90.14(7) . 3_666 ?
O7 Co1 O12 92.74(8) . 3_666 ?
O2 Co2 O5 91.92(8) . . ?
O2 Co2 O10 93.98(7) . 1_565 ?
O5 Co2 O10 100.42(8) . 1_565 ?
O2 Co2 O13 95.26(7) . . ?
O5 Co2 O13 88.30(7) . . ?
O10 Co2 O13 167.07(8) 1_565 . ?
O2 Co2 O9 170.95(7) . 1_565 ?
O5 Co2 O9 88.07(7) . 1_565 ?
O10 Co2 O9 77.14(7) 1_565 1_565 ?
O13 Co2 O9 93.78(7) . 1_565 ?
O2 Co2 O14 89.07(8) . 3_777 ?
O5 Co2 O14 164.80(7) . 3_777 ?
O10 Co2 O14 94.64(7) 1_565 3_777 ?
O13 Co2 O14 76.50(7) . 3_777 ?
O9 Co2 O14 93.31(7) 1_565 3_777 ?
O2 P1 O1 118.18(11) . . ?
O2 P1 O3 107.99(11) . . ?
O1 P1 O3 109.84(11) . . ?
O2 P1 H1 107.2 . . ?
O1 P1 H1 113.4 . . ?
O3 P1 H1 98.3 . . ?
O4 P2 O5 118.07(11) . . ?
O4 P2 O6 107.25(12) . . ?
O5 P2 O6 110.58(11) . . ?
O4 P2 H2 107.2 . . ?
O5 P2 H2 109.5 . . ?
O6 P2 H2 103.2 . . ?
P1 O1 Co1 122.86(11) . . ?
P1 O2 Co2 146.78(12) . . ?
P1 O3 H3A 114.3 . . ?
P2 O4 Co1 147.33(13) . . ?
P2 O5 Co2 128.57(11) . . ?
P2 O6 H6A 116.8 . . ?
C1 O7 Co1 114.63(16) . . ?
C2 O8 Co1 115.88(16) . . ?
C2 O9 Co2 113.77(16) . 1_545 ?
C1 O10 Co2 115.57(16) . 1_545 ?
C3 O11 Co1 115.59(15) . . ?
C3 O12 Co1 113.67(15) . 3_666 ?
C4 O13 Co2 114.47(15) . . ?
C4 O14 Co2 112.75(15) . 3_777 ?
O10 C1 O7 126.5(2) . . ?
O10 C1 C2 117.5(2) . . ?
O7 C1 C2 116.0(2) . . ?
O8 C2 O9 127.3(2) . . ?
O8 C2 C1 116.7(2) . . ?
O9 C2 C1 116.0(2) . . ?
O11 C3 O12 126.7(2) . . ?
O11 C3 C3 117.1(3) . 3_666 ?
O12 C3 C3 116.2(3) . 3_666 ?
O13 C4 O14 126.8(2) . . ?
O13 C4 C4 117.2(3) . 3_777 ?
O14 C4 C4 116.1(3) . 3_777 ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C6 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 C7 109.3(2) . . ?
N1 C6 C5 108.9(2) . . ?
C7 C6 C5 111.3(2) . . ?
N1 C6 H6 109.1 . . ?
C7 C6 H6 109.1 . . ?
C5 C6 H6 109.1 . . ?
N2 C7 C6 110.5(2) . . ?
N2 C7 H7A 109.6 . . ?
C6 C7 H7A 109.6 . . ?
N2 C7 H7B 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
N2 C8 C9 111.1(2) . . ?
N2 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N2 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N1 C9 C8 108.9(2) . . ?
N1 C9 C10 109.6(2) . . ?
C8 C9 C10 111.1(2) . . ?
N1 C9 H9 109.0 . . ?
C8 C9 H9 109.0 . . ?
C10 C9 H9 109.0 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 N1 C9 111.9(2) . . ?
C6 N1 H1A 109.2 . . ?
C9 N1 H1A 109.2 . . ?
C6 N1 H1B 109.2 . . ?
C9 N1 H1B 109.2 . . ?
H1A N1 H1B 107.9 . . ?
C8 N2 C7 111.2(2) . . ?
C8 N2 H2A 109.4 . . ?
C7 N2 H2A 109.4 . . ?
C8 N2 H2B 109.4 . . ?
C7 N2 H2B 109.4 . . ?
H2A N2 H2B 108.0 . . ?

_refine_diff_density_max         0.587
_refine_diff_density_min         -0.929
_refine_diff_density_rms         0.117

