# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_twin5
_database_code_depnum_ccdc_archive 'CCDC 1552746'
_audit_update_record             
;
2017-05-28 deposited with the CCDC.	2019-07-22 downloaded from the CCDC.
;
_audit_creation_date             2017-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H18 Co N8 O10, 2(H2 O)'
_chemical_formula_sum            'C12 H22 Co N8 O12'
_chemical_formula_weight         529.30
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5940(4)
_cell_length_b                   7.8777(5)
_cell_length_c                   9.2102(5)
_cell_angle_alpha                98.868(2)
_cell_angle_beta                 101.319(2)
_cell_angle_gamma                114.712(2)
_cell_volume                     473.22(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5026
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.355
_cell_measurement_theta_min      2.953
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.995
_exptl_absorpt_correction_T_max  0.745686
_exptl_absorpt_correction_T_min  0.636574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0740 before and 0.0368 after correction.
 The Ratio of minimum to maximum transmission not present.
 The λ/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1906 before and 0.0387 after correction.
 The Ratio of minimum to maximum transmission is 0.85.
 The λ/2 correction factor is Not present

Final HKLF 4 output contains 15294 reflections, Rint = 0.0316
 (13725 with I > 3sig(I), Rint = 0.0312)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light pink'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.857
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             273
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2347
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         28.355
_diffrn_reflns_theta_min         3.086
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Quest CMOS'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2287
_reflns_number_total             2347
_reflns_special_details          
;
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0278
_refine_ls_restrained_S_all      1.145
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0514P)²+0.1476P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0827
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5657(14)
 0.4343(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
3.a Free rotating group:
 O11(H11A,H11B)
3.b Rotating group:
 O10(H10A,H10B)
3.c Secondary CH2 refined with riding coordinates:
 N4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
3.d Aromatic/amide H refined with riding coordinates:
 N2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.500000 1.000000 1.000000 0.01089(11) Uani 1 2 d S T P . .
N1 N 0.9210(2) 0.7122(2) 0.45270(18) 0.0131(3) Uani 1 1 d . . . . .
O2 O 1.0751(2) 0.4684(2) 0.18699(16) 0.0181(3) Uani 1 1 d . . . . .
N2 N 1.0325(2) 0.6444(2) 0.38584(18) 0.0135(3) Uani 1 1 d . . . . .
H2 H 1.159172 0.686091 0.439018 0.016 Uiso 1 1 calc R . . . .
C2 C 0.9665(3) 0.5182(3) 0.2444(2) 0.0126(3) Uani 1 1 d . . . . .
O3 O 0.4642(2) 0.4586(2) 0.14821(15) 0.0148(3) Uani 1 1 d . . . . .
N3 N 0.7631(2) 0.4508(2) 0.17091(17) 0.0109(3) Uani 1 1 d . . . . .
C3 C 0.6388(3) 0.5155(2) 0.2237(2) 0.0109(3) Uani 1 1 d . . . . .
N4 N 0.6802(2) 0.3132(2) 0.02512(17) 0.0117(3) Uani 1 1 d . . . . .
H4A H 0.785257 0.327295 -0.013771 0.014 Uiso 1 1 calc R . . . .
H4B H 0.600707 0.349012 -0.037110 0.014 Uiso 1 1 calc R . . . .
C4 C 0.7353(3) 0.6540(2) 0.3775(2) 0.0116(3) Uani 1 1 d . . . . .
C5 C 0.6042(3) 0.7241(3) 0.4438(2) 0.0126(3) Uani 1 1 d . . . . .
H5A H 0.473513 0.611381 0.432861 0.015 Uiso 1 1 calc R . . . .
H5B H 0.575339 0.808969 0.384576 0.015 Uiso 1 1 calc R . . . .
C6 C 0.7031(3) 0.8358(3) 0.6129(2) 0.0127(3) Uani 1 1 d . . . . .
H6A H 0.754336 0.759889 0.668339 0.015 Uiso 1 1 calc R . . . .
H6B H 0.820923 0.959862 0.621306 0.015 Uiso 1 1 calc R . . . .
C7 C 0.5613(3) 0.8785(2) 0.6905(2) 0.0112(3) Uani 1 1 d . . . . .
O8 O 0.6405(2) 0.97123(19) 0.83264(15) 0.0139(3) Uani 1 1 d . . . . .
O9 O 0.3803(2) 0.8221(2) 0.61905(15) 0.0177(3) Uani 1 1 d . . . . .
O10 O 0.7317(2) 0.9980(2) 1.15841(16) 0.0216(3) Uani 1 1 d . . . . .
H10A H 0.797673 1.108921 1.228470 0.032 Uiso 1 1 d GR . . . .
H10B H 0.814915 0.979693 1.112269 0.032 Uiso 1 1 d GR . . . .
O11 O 0.9456(2) 0.82166(19) 1.08409(16) 0.0163(3) Uani 1 1 d . . . . .
H11A H 1.073902 0.902111 1.107503 0.024 Uiso 1 1 d G . . . .
H11B H 0.901450 0.759723 0.987334 0.024 Uiso 1 1 d G . . . .


_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 N4 2.2117(16) 1_566 ?
Co1 N4 2.2117(16) 2_666 ?
Co1 O8 2.0750(13) . ?
Co1 O8 2.0749(13) 2_677 ?
Co1 O10 2.0607(14) . ?
Co1 O10 2.0607(14) 2_677 ?
N1 N2 1.364(2) . ?
N1 C4 1.288(2) . ?
O2 C2 1.221(2) . ?
N2 H2 0.8800 . ?
N2 C2 1.366(2) . ?
C2 N3 1.385(2) . ?
O3 C3 1.220(2) . ?
N3 C3 1.376(2) . ?
N3 N4 1.4222(19) . ?
C3 C4 1.477(2) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
C4 C5 1.504(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.526(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.522(2) . ?
C7 O8 1.280(2) . ?
C7 O9 1.251(2) . ?
O10 H10A 0.8739 . ?
O10 H10B 0.8740 . ?
O11 H11A 0.8700 . ?
O11 H11B 0.8698 . ?

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
N4 Co1 N4 180.0 2_666 1_566 ?
O8 Co1 N4 83.33(6) 2_677 2_666 ?
O8 Co1 N4 96.67(5) 2_677 1_566 ?
O8 Co1 N4 83.33(6) . 1_566 ?
O8 Co1 N4 96.67(5) . 2_666 ?
O8 Co1 O8 180.0 2_677 . ?
O10 Co1 N4 91.58(6) 2_677 2_666 ?
O10 Co1 N4 88.42(6) 2_677 1_566 ?
O10 Co1 N4 91.58(6) . 1_566 ?
O10 Co1 N4 88.42(6) . 2_666 ?
O10 Co1 O8 91.06(5) . 2_677 ?
O10 Co1 O8 88.94(5) . . ?
O10 Co1 O8 91.06(5) 2_677 . ?
O10 Co1 O8 88.94(5) 2_677 2_677 ?
O10 Co1 O10 180.00(9) . 2_677 ?
C4 N1 N2 118.26(15) . . ?
N1 N2 H2 116.8 . . ?
N1 N2 C2 126.31(16) . . ?
C2 N2 H2 116.8 . . ?
O2 C2 N2 123.71(17) . . ?
O2 C2 N3 122.65(16) . . ?
N2 C2 N3 113.63(15) . . ?
C2 N3 N4 117.31(14) . . ?
C3 N3 C2 124.97(14) . . ?
C3 N3 N4 117.59(14) . . ?
O3 C3 N3 121.46(16) . . ?
O3 C3 C4 124.50(16) . . ?
N3 C3 C4 114.03(16) . . ?
Co1 N4 H4A 107.0 1_544 . ?
Co1 N4 H4B 107.0 1_544 . ?
N3 N4 Co1 121.38(11) . 1_544 ?
N3 N4 H4A 107.0 . . ?
N3 N4 H4B 107.0 . . ?
H4A N4 H4B 106.7 . . ?
N1 C4 C3 122.52(16) . . ?
N1 C4 C5 121.06(15) . . ?
C3 C4 C5 116.41(16) . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
C4 C5 C6 112.54(15) . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
C5 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 C5 113.79(15) . . ?
C7 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
O8 C7 C6 114.97(16) . . ?
O9 C7 C6 121.36(15) . . ?
O9 C7 O8 123.66(16) . . ?
C7 O8 Co1 129.33(12) . . ?
Co1 O10 H10A 109.8 . . ?
Co1 O10 H10B 109.5 . . ?
H10A O10 H10B 109.2 . . ?
H11A O11 H11B 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
N1 N2 C2 O2 176.79(18) . . . . ?
N1 N2 C2 N3 -3.3(3) . . . . ?
N1 C4 C5 C6 -10.2(2) . . . . ?
O2 C2 N3 C3 -173.66(18) . . . . ?
O2 C2 N3 N4 2.1(3) . . . . ?
N2 N1 C4 C3 0.9(3) . . . . ?
N2 N1 C4 C5 -179.48(16) . . . . ?
N2 C2 N3 C3 6.4(3) . . . . ?
N2 C2 N3 N4 -177.83(15) . . . . ?
C2 N3 C3 O3 175.16(17) . . . . ?
C2 N3 C3 C4 -5.8(3) . . . . ?
C2 N3 N4 Co1 100.51(16) . . . 1_544 ?
O3 C3 C4 N1 -179.15(18) . . . . ?
O3 C3 C4 C5 1.2(3) . . . . ?
N3 C3 C4 N1 1.8(3) . . . . ?
N3 C3 C4 C5 -177.80(15) . . . . ?
C3 N3 N4 Co1 -83.45(17) . . . 1_544 ?
C3 C4 C5 C6 169.41(15) . . . . ?
N4 N3 C3 O3 -0.5(3) . . . . ?
N4 N3 C3 C4 178.50(15) . . . . ?
C4 N1 N2 C2 -0.1(3) . . . . ?
C4 C5 C6 C7 -170.02(15) . . . . ?
C5 C6 C7 O8 179.69(15) . . . . ?
C5 C6 C7 O9 1.1(2) . . . . ?
C6 C7 O8 Co1 -161.98(12) . . . . ?
O9 C7 O8 Co1 16.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.5657(14)
2 0.4343(14)

