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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mx94_12

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H26 Co2 N2 O8 P2'
_chemical_formula_sum            'C12 H26 Co2 N2 O8 P2'
_chemical_formula_weight         506.15

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'
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           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   15.0954(6)
_cell_length_b                   11.5689(4)
_cell_length_c                   10.6232(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.192(4)
_cell_angle_gamma                90.00
_cell_volume                     1741.19(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    7545
_cell_measurement_theta_min      2.2682
_cell_measurement_theta_max      32.3145

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.931
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040
_exptl_absorpt_coefficient_mu    2.135
_exptl_absorpt_correction_T_min  0.92255
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_detector_area_resol_mean 10.3389
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18166
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3992
_reflns_number_gt                3699
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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.

 The unit cell was metrically similar to a C-centred orthorhombic cell 
 (transformation matrix 0 0 1 -2 0 -1 0 -1 0) and the data was treated as a
 pseudo merohedral twin (twin law -1 0 -1 0 -1 0 0 0 1 corresponding to a 
 180 deg rotation about a) and refined with BASF = 0.03 which reduced R1 by 
 approximately 2%. However, there remained a residual electron density peak 
 of 3.3 eÅ₋₃ located 1.95 Å from O8 and is presumed to be a 
 consequence of further unaccounted for twinning. Attempts to model the 
 electron density as a disordered water molecule were unsuccessful. 
;

_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)+(0.0395P)²+4.9157P] 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         3992
_refine_ls_number_parameters     252
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0892
_refine_ls_wR_factor_gt          0.0853
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.036
_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 0.40523(3) 0.30861(3) 0.19775(4) 0.00856(10) Uani 1 1 d . . .
Co2 Co 0.59740(3) 0.35517(3) 0.15040(4) 0.00914(10) Uani 1 1 d . . .
P1 P 0.37287(5) 0.37308(6) -0.09034(7) 0.00742(14) Uani 1 1 d . . .
P2 P -0.38221(5) 0.20544(7) -0.05196(7) 0.01319(16) Uani 1 1 d . . .
O1 O 0.45015(14) 0.37355(17) 0.0487(2) 0.0099(4) Uani 1 1 d . . .
O2 O 0.38019(14) 0.47381(17) -0.1787(2) 0.0100(4) Uani 1 1 d . . .
O3 O 0.36364(14) 0.25782(18) -0.1603(2) 0.0116(4) Uani 1 1 d . . .
O4 O -0.44888(14) 0.18721(19) -0.1964(2) 0.0126(4) Uani 1 1 d . . .
O5 O -0.41018(18) 0.1516(3) 0.0571(3) 0.0350(7) Uani 1 1 d . . .
O6 O -0.36499(17) 0.3343(2) -0.0169(3) 0.0288(6) Uani 1 1 d . . .
O7 O 0.38940(16) 0.4886(2) 0.2407(2) 0.0173(5) Uani 1 1 d D . .
O8 O 0.42438(15) 0.14131(18) 0.1234(2) 0.0124(4) Uani 1 1 d D . .
N1 N 0.25751(16) 0.3163(2) 0.0538(2) 0.0090(5) Uani 1 1 d . . .
N2 N -0.25639(16) 0.1748(2) -0.1824(2) 0.0104(5) Uani 1 1 d . . .
C1 C 0.19286(19) 0.3641(3) 0.1189(3) 0.0111(5) Uani 1 1 d . . .
H1A H 0.2121 0.4445 0.1471 0.013 Uiso 1 1 calc R . .
H1B H 0.2001 0.3185 0.2008 0.013 Uiso 1 1 calc R . .
C2 C 0.08828(19) 0.3639(2) 0.0297(3) 0.0113(5) Uani 1 1 d . . .
H2A H 0.0500 0.3970 0.0800 0.014 Uiso 1 1 calc R . .
H2B H 0.0794 0.4128 -0.0502 0.014 Uiso 1 1 calc R . .
C3 C 0.05464(19) 0.2405(2) -0.0150(3) 0.0109(5) Uani 1 1 d . . .
H3 H 0.0617 0.1937 0.0670 0.013 Uiso 1 1 calc R . .
C4 C 0.12081(19) 0.1897(3) -0.0825(3) 0.0120(5) Uani 1 1 d . . .
H4A H 0.1041 0.1076 -0.1045 0.014 Uiso 1 1 calc R . .
H4B H 0.1110 0.2313 -0.1677 0.014 Uiso 1 1 calc R . .
C5 C 0.22504(19) 0.1975(2) 0.0048(3) 0.0111(5) Uani 1 1 d . . .
H5A H 0.2366 0.1459 0.0832 0.013 Uiso 1 1 calc R . .
H5B H 0.2635 0.1686 -0.0475 0.013 Uiso 1 1 calc R . .
C6 C 0.26383(19) 0.3938(2) -0.0546(3) 0.0100(5) Uani 1 1 d . . .
H6A H 0.2602 0.4751 -0.0279 0.012 Uiso 1 1 calc R . .
H6B H 0.2092 0.3790 -0.1373 0.012 Uiso 1 1 calc R . .
C7 C -0.2197(2) 0.2952(2) -0.1703(3) 0.0117(5) Uani 1 1 d . . .
H7A H -0.2620 0.3456 -0.1411 0.014 Uiso 1 1 calc R . .
H7B H -0.2224 0.3219 -0.2600 0.014 Uiso 1 1 calc R . .
C8 C -0.1185(2) 0.3102(3) -0.0721(3) 0.0134(6) Uani 1 1 d . . .
H8A H -0.0991 0.3919 -0.0728 0.016 Uiso 1 1 calc R . .
H8B H -0.1164 0.2914 0.0198 0.016 Uiso 1 1 calc R . .
C9 C -0.04940(19) 0.2324(3) -0.1090(3) 0.0107(5) Uani 1 1 d . . .
H9 H -0.0516 0.2553 -0.2008 0.013 Uiso 1 1 calc R . .
C10 C -0.0860(2) 0.1081(3) -0.1180(3) 0.0142(6) Uani 1 1 d . . .
H10A H -0.0455 0.0571 -0.1500 0.017 Uiso 1 1 calc R . .
H10B H -0.0817 0.0816 -0.0274 0.017 Uiso 1 1 calc R . .
C11 C -0.18785(19) 0.0976(3) -0.2125(3) 0.0132(6) Uani 1 1 d . . .
H11A H -0.1898 0.1139 -0.3049 0.016 Uiso 1 1 calc R . .
H11B H -0.2086 0.0167 -0.2104 0.016 Uiso 1 1 calc R . .
C12 C -0.2742(2) 0.1387(3) -0.0592(3) 0.0130(6) Uani 1 1 d . . .
H12A H -0.2201 0.1617 0.0208 0.016 Uiso 1 1 calc R . .
H12B H -0.2801 0.0535 -0.0582 0.016 Uiso 1 1 calc R . .
H1W H 0.400(4) 0.538(3) 0.189(3) 0.052(16) Uiso 1 1 d D . .
H2W H 0.400(3) 0.521(3) 0.315(2) 0.043(14) Uiso 1 1 d D . .
H3W H 0.430(3) 0.090(2) 0.181(3) 0.022(10) Uiso 1 1 d D . .
H4W H 0.462(3) 0.126(4) 0.083(4) 0.056(17) Uiso 1 1 d D . .


_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 O3 1.978(2) 4_566 ?
Co1 O1 2.067(2) . ?
Co1 O4 2.099(2) 4_666 ?
Co1 O8 2.147(2) . ?
Co1 O7 2.162(2) . ?
Co1 N1 2.228(2) . ?
Co2 O2 2.012(2) 3_665 ?
Co2 O4 2.040(2) 4_666 ?
Co2 O6 2.058(3) 1_655 ?
Co2 O1 2.120(2) . ?
Co2 N2 2.332(2) 4_666 ?
P1 O3 1.509(2) . ?
P1 O2 1.524(2) . ?
P1 O1 1.534(2) . ?
P1 C6 1.828(3) . ?
P2 O5 1.499(3) . ?
P2 O4 1.531(2) . ?
P2 O6 1.537(3) . ?
P2 C12 1.830(3) . ?
O2 Co2 2.012(2) 3_665 ?
O3 Co1 1.978(2) 4_565 ?
O4 Co2 2.040(2) 4_465 ?
O4 Co1 2.099(2) 4_465 ?
O6 Co2 2.058(3) 1_455 ?
N1 C1 1.485(3) . ?
N1 C6 1.488(4) . ?
N1 C5 1.491(4) . ?
N2 C11 1.482(4) . ?
N2 C12 1.484(4) . ?
N2 C7 1.488(4) . ?
N2 Co2 2.332(2) 4_465 ?
C1 C2 1.535(4) . ?
C2 C3 1.535(4) . ?
C3 C4 1.533(4) . ?
C3 C9 1.546(4) . ?
C4 C5 1.528(4) . ?
C7 C8 1.534(4) . ?
C8 C9 1.528(4) . ?
C9 C10 1.531(4) . ?
C10 C11 1.523(4) . ?

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
O3 Co1 O1 178.40(8) 4_566 . ?
O3 Co1 O4 98.67(8) 4_566 4_666 ?
O1 Co1 O4 80.86(8) . 4_666 ?
O3 Co1 O8 92.80(8) 4_566 . ?
O1 Co1 O8 85.66(8) . . ?
O4 Co1 O8 88.19(8) 4_666 . ?
O3 Co1 O7 97.22(9) 4_566 . ?
O1 Co1 O7 84.33(8) . . ?
O4 Co1 O7 92.10(9) 4_666 . ?
O8 Co1 O7 169.81(8) . . ?
O3 Co1 N1 91.89(9) 4_566 . ?
O1 Co1 N1 88.56(8) . . ?
O4 Co1 N1 169.42(8) 4_666 . ?
O8 Co1 N1 90.75(8) . . ?
O7 Co1 N1 87.10(9) . . ?
O2 Co2 O4 101.72(8) 3_665 4_666 ?
O2 Co2 O6 99.33(10) 3_665 1_655 ?
O4 Co2 O6 158.94(10) 4_666 1_655 ?
O2 Co2 O1 94.02(8) 3_665 . ?
O4 Co2 O1 80.97(8) 4_666 . ?
O6 Co2 O1 97.18(9) 1_655 . ?
O2 Co2 N2 88.06(8) 3_665 4_666 ?
O4 Co2 N2 81.45(8) 4_666 4_666 ?
O6 Co2 N2 99.77(9) 1_655 4_666 ?
O1 Co2 N2 162.36(8) . 4_666 ?
O3 P1 O2 112.72(12) . . ?
O3 P1 O1 112.79(12) . . ?
O2 P1 O1 113.43(11) . . ?
O3 P1 C6 106.32(12) . . ?
O2 P1 C6 106.85(12) . . ?
O1 P1 C6 103.86(12) . . ?
O5 P2 O4 117.01(15) . . ?
O5 P2 O6 106.55(17) . . ?
O4 P2 O6 111.97(14) . . ?
O5 P2 C12 110.48(14) . . ?
O4 P2 C12 100.78(13) . . ?
O6 P2 C12 109.93(14) . . ?
P1 O1 Co1 113.25(11) . . ?
P1 O1 Co2 143.65(12) . . ?
Co1 O1 Co2 97.86(8) . . ?
P1 O2 Co2 134.74(12) . 3_665 ?
P1 O3 Co1 135.96(13) . 4_565 ?
P2 O4 Co2 123.00(12) . 4_465 ?
P2 O4 Co1 137.62(12) . 4_465 ?
Co2 O4 Co1 99.37(9) 4_465 4_465 ?
P2 O6 Co2 104.43(15) . 1_455 ?
C1 N1 C6 111.4(2) . . ?
C1 N1 C5 108.4(2) . . ?
C6 N1 C5 112.7(2) . . ?
C1 N1 Co1 110.97(17) . . ?
C6 N1 Co1 103.82(16) . . ?
C5 N1 Co1 109.48(16) . . ?
C11 N2 C12 111.9(2) . . ?
C11 N2 C7 108.4(2) . . ?
C12 N2 C7 111.2(2) . . ?
C11 N2 Co2 107.09(17) . 4_465 ?
C12 N2 Co2 102.62(16) . 4_465 ?
C7 N2 Co2 115.51(17) . 4_465 ?
N1 C1 C2 114.4(2) . . ?
C3 C2 C1 110.6(2) . . ?
C4 C3 C2 107.6(2) . . ?
C4 C3 C9 110.8(2) . . ?
C2 C3 C9 114.2(2) . . ?
C5 C4 C3 113.2(2) . . ?
N1 C5 C4 114.3(2) . . ?
N1 C6 P1 112.62(19) . . ?
N2 C7 C8 114.7(2) . . ?
C9 C8 C7 111.5(2) . . ?
C8 C9 C10 107.8(2) . . ?
C8 C9 C3 115.5(2) . . ?
C10 C9 C3 111.2(2) . . ?
C11 C10 C9 112.1(2) . . ?
N2 C11 C10 115.5(2) . . ?
N2 C12 P2 110.70(19) . . ?

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
O7 H1W O6 0.839(10) 2.27(2) 3.064(4) 157(5) 3_565
O7 H2W O5 0.840(10) 2.00(2) 2.793(3) 158(4) 2
O8 H3W O2 0.838(10) 2.03(2) 2.758(3) 146(3) 4_566
O8 H4W O5 0.840(10) 2.06(3) 2.821(3) 150(5) 1_655

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         3.293
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.101
_database_code_depnum_ccdc_archive 'CCDC 986602'
