# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_ada106
_database_code_depnum_ccdc_archive 'CCDC 1866130'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;University of Montreal
Canada
;
_audit_update_record             
;
2018-09-12 deposited with the CCDC.	2019-04-15 downloaded from the CCDC.
;
_audit_creation_date             2016-08-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 N14 Ni O10, H12 Ni O6'
_chemical_formula_sum            'C12 H22 N14 Ni2 O16'
_chemical_formula_weight         735.85
_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 0.0140 0.0070 '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 0.0240 0.0130 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -1.3360 3.2900 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0390 0.0240 '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                   7.3698(3)
_cell_length_b                   8.6190(3)
_cell_length_c                   9.1797(3)
_cell_angle_alpha                78.027(2)
_cell_angle_beta                 84.389(2)
_cell_angle_gamma                86.957(2)
_cell_volume                     567.36(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9990
_cell_measurement_temperature    100
_cell_measurement_theta_max      60.660
_cell_measurement_theta_min      4.301
_shelx_estimated_absorpt_T_max   0.641
_shelx_estimated_absorpt_T_min   0.548
_exptl_absorpt_coefficient_mu    9.766
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1321 before and 0.0879 after correction.
The Ratio of minimum to maximum transmission is 0.8205.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.154
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0823
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            18351
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.614
_diffrn_reflns_theta_min         4.300
_diffrn_ambient_temperature      100
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1896
_reflns_number_total             2490
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
SAINT (2013) V8.37A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2013) V8.37A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         1.765
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.164
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         2490
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0742
_refine_ls_restrained_S_all      1.101
_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)+(0.0854P)²+3.4341P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1723
_refine_ls_wR_factor_ref         0.1909
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_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
Ni1 Ni 1.0000 0.0000 0.0000 0.0201(3) Uani 1 2 d S T P . .
O1 O 1.0463(6) 0.2024(5) 0.0836(5) 0.0224(9) Uani 1 1 d . . . . .
O2 O 0.5476(6) -0.0049(5) 0.7572(5) 0.0254(10) Uani 1 1 d . . . . .
O3 O 0.7857(6) 0.7617(5) 0.4956(5) 0.0244(10) Uani 1 1 d . . . . .
O4 O 0.7245(6) 0.0512(6) 0.0174(6) 0.0243(10) Uani 1 1 d . . . . .
H4A H 0.664(10) 0.037(9) -0.068(9) 0.03(2) Uiso 1 1 d . . . . .
H4B H 0.674(14) 0.012(12) 0.083(12) 0.05(3) Uiso 1 1 d . . . . .
O5 O 1.0117(6) -0.1360(6) 0.2071(5) 0.0236(10) Uani 1 1 d . . . . .
H5A H 0.971(9) -0.229(9) 0.239(7) 0.016(16) Uiso 1 1 d . . . . .
H5B H 0.969(10) -0.085(9) 0.267(9) 0.03(2) Uiso 1 1 d . . . . .
N1 N 0.8855(7) 0.1259(6) 0.3093(6) 0.0235(11) Uani 1 1 d . . . . .
N2 N 0.7118(7) 0.0632(7) 0.5340(6) 0.0237(12) Uani 1 1 d . . . . .
H2 H 0.730(10) -0.034(10) 0.532(9) 0.03(2) Uiso 1 1 d . . . . .
N3 N 0.9725(7) 0.3954(6) 0.2160(6) 0.0214(11) Uani 1 1 d . . . . .
N4 N 0.7875(7) 0.3235(6) 0.4435(6) 0.0217(11) Uani 1 1 d . . . . .
N5 N 0.5906(7) 0.2590(6) 0.6660(6) 0.0230(11) Uani 1 1 d . . . . .
N6 N 0.8778(7) 0.5846(6) 0.3526(6) 0.0236(11) Uani 1 1 d . . . . .
N7 N 0.6769(7) 0.5165(6) 0.5777(6) 0.0241(12) Uani 1 1 d . . . . .
C1 C 0.9701(8) 0.2413(7) 0.2002(7) 0.0233(13) Uani 1 1 d . . . . .
C2 C 0.7978(8) 0.1682(7) 0.4251(7) 0.0206(12) Uani 1 1 d . . . . .
C3 C 0.6132(8) 0.1025(7) 0.6600(7) 0.0201(12) Uani 1 1 d . . . . .
C4 C 0.8808(8) 0.4368(7) 0.3346(7) 0.0219(13) Uani 1 1 d . . . . .
C5 C 0.6826(8) 0.3670(7) 0.5660(6) 0.0188(12) Uani 1 1 d . . . . .
C6 C 0.7791(8) 0.6240(7) 0.4763(7) 0.0221(13) Uani 1 1 d . . . . .
Ni2 Ni 0.5000 0.5000 1.0000 0.0213(3) Uani 1 2 d S T P . .
O6 O 0.4897(6) 0.6517(6) 0.7949(5) 0.0237(10) Uani 1 1 d . . . . .
H6A H 0.526(11) 0.733(11) 0.788(9) 0.04(2) Uiso 1 1 d . . . . .
H6B H 0.556(12) 0.614(10) 0.736(9) 0.04(2) Uiso 1 1 d . . . . .
O7 O 0.6130(7) 0.6780(6) 1.0726(5) 0.0267(11) Uani 1 1 d . . . . .
H7A H 0.720(12) 0.709(10) 1.047(10) 0.04(2) Uiso 1 1 d . . . . .
H7B H 0.566(11) 0.698(9) 1.137(9) 0.02(2) Uiso 1 1 d . . . . .
O8 O 0.2557(6) 0.5887(7) 1.0726(6) 0.0287(11) Uani 1 1 d . . . . .
H8A H 0.156(8) 0.537(7) 1.114(7) 0.006(14) Uiso 1 1 d . . . . .
H8B H 0.232(9) 0.664(8) 1.068(7) 0.004(17) Uiso 1 1 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
Ni1 O1 2.102(4) 2_755 ?
Ni1 O1 2.102(4) . ?
Ni1 O4 2.053(5) 2_755 ?
Ni1 O4 2.053(5) . ?
Ni1 O5 2.023(5) 2_755 ?
Ni1 O5 2.023(5) . ?
O1 C1 1.259(7) . ?
O2 C3 1.227(7) . ?
O3 C6 1.240(7) . ?
O4 H4A 0.97(8) . ?
O4 H4B 0.71(10) . ?
O5 H5A 0.85(7) . ?
O5 H5B 0.81(8) . ?
N1 C1 1.382(8) . ?
N1 C2 1.297(7) . ?
N2 H2 0.84(8) . ?
N2 C2 1.335(8) . ?
N2 C3 1.398(7) . ?
N3 C1 1.367(8) . ?
N3 C4 1.327(7) . ?
N4 C2 1.381(8) . ?
N4 C4 1.399(8) . ?
N4 C5 1.406(7) . ?
N5 C3 1.363(8) . ?
N5 C5 1.327(8) . ?
N6 C4 1.317(8) . ?
N6 C6 1.381(7) . ?
N7 C5 1.314(8) . ?
N7 C6 1.368(8) . ?
Ni2 O6 2.063(5) . ?
Ni2 O6 2.063(5) 2_667 ?
Ni2 O7 2.040(4) . ?
Ni2 O7 2.040(4) 2_667 ?
Ni2 O8 2.025(5) . ?
Ni2 O8 2.025(5) 2_667 ?
O6 H6A 0.75(9) . ?
O6 H6B 0.80(9) . ?
O7 H7A 0.84(9) . ?
O7 H7B 0.71(8) . ?
O8 H8A 0.89(6) . ?
O8 H8B 0.66(7) . ?

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 O1 180.0 . 2_755 ?
O4 Ni1 O1 90.01(17) . 2_755 ?
O4 Ni1 O1 89.99(17) . . ?
O4 Ni1 O1 89.98(17) 2_755 2_755 ?
O4 Ni1 O1 90.01(17) 2_755 . ?
O4 Ni1 O4 180.0 2_755 . ?
O5 Ni1 O1 90.02(17) 2_755 . ?
O5 Ni1 O1 90.02(17) . 2_755 ?
O5 Ni1 O1 89.98(17) . . ?
O5 Ni1 O1 89.98(17) 2_755 2_755 ?
O5 Ni1 O4 83.07(19) 2_755 . ?
O5 Ni1 O4 96.93(19) . . ?
O5 Ni1 O4 83.07(19) . 2_755 ?
O5 Ni1 O4 96.93(19) 2_755 2_755 ?
O5 Ni1 O5 180.0 . 2_755 ?
C1 O1 Ni1 127.3(4) . . ?
Ni1 O4 H4A 114(4) . . ?
Ni1 O4 H4B 117(8) . . ?
H4A O4 H4B 108(9) . . ?
Ni1 O5 H5A 127(4) . . ?
Ni1 O5 H5B 108(5) . . ?
H5A O5 H5B 105(7) . . ?
C2 N1 C1 118.5(5) . . ?
C2 N2 H2 118(5) . . ?
C2 N2 C3 124.1(5) . . ?
C3 N2 H2 118(5) . . ?
C4 N3 C1 118.9(5) . . ?
C2 N4 C4 118.0(5) . . ?
C2 N4 C5 121.0(5) . . ?
C4 N4 C5 121.1(5) . . ?
C5 N5 C3 120.0(5) . . ?
C4 N6 C6 119.1(5) . . ?
C5 N7 C6 119.8(5) . . ?
O1 C1 N1 118.7(5) . . ?
O1 C1 N3 119.6(6) . . ?
N3 C1 N1 121.7(5) . . ?
N1 C2 N2 121.7(6) . . ?
N1 C2 N4 122.4(5) . . ?
N2 C2 N4 116.0(5) . . ?
O2 C3 N2 118.6(5) . . ?
O2 C3 N5 123.5(5) . . ?
N5 C3 N2 117.9(5) . . ?
N3 C4 N4 120.5(5) . . ?
N6 C4 N3 120.6(5) . . ?
N6 C4 N4 118.9(5) . . ?
N5 C5 N4 120.4(5) . . ?
N7 C5 N4 118.4(5) . . ?
N7 C5 N5 121.2(5) . . ?
O3 C6 N6 118.2(5) . . ?
O3 C6 N7 119.4(5) . . ?
N7 C6 N6 122.3(5) . . ?
O6 Ni2 O6 180.0(2) . 2_667 ?
O7 Ni2 O6 87.8(2) 2_667 2_667 ?
O7 Ni2 O6 92.2(2) . 2_667 ?
O7 Ni2 O6 87.8(2) . . ?
O7 Ni2 O6 92.2(2) 2_667 . ?
O7 Ni2 O7 180.0(2) 2_667 . ?
O8 Ni2 O6 90.5(2) . . ?
O8 Ni2 O6 90.5(2) 2_667 2_667 ?
O8 Ni2 O6 89.5(2) 2_667 . ?
O8 Ni2 O6 89.5(2) . 2_667 ?
O8 Ni2 O7 93.6(2) . 2_667 ?
O8 Ni2 O7 86.4(2) . . ?
O8 Ni2 O7 86.4(2) 2_667 2_667 ?
O8 Ni2 O7 93.6(2) 2_667 . ?
O8 Ni2 O8 180.0 . 2_667 ?
Ni2 O6 H6A 117(7) . . ?
Ni2 O6 H6B 107(6) . . ?
H6A O6 H6B 104(8) . . ?
Ni2 O7 H7A 125(5) . . ?
Ni2 O7 H7B 114(6) . . ?
H7A O7 H7B 118(8) . . ?
Ni2 O8 H8A 129(4) . . ?
Ni2 O8 H8B 127(6) . . ?
H8A O8 H8B 104(7) . . ?

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
O4 H4A O2 0.97(8) 2.00(8) 2.965(7) 177(7) 1_554
O4 H4B O2 0.71(10) 2.08(10) 2.719(6) 151(11) 2_656
O5 H5A N6 0.85(7) 1.85(8) 2.687(7) 166(6) 1_545
O5 H5B O3 0.81(8) 2.54(8) 2.982(6) 116(6) 1_545
O5 H5B N1 0.81(8) 1.99(8) 2.707(7) 148(7) .
N2 H2 O3 0.84(8) 1.88(8) 2.714(7) 170(8) 1_545
O6 H6A O2 0.75(9) 2.23(9) 2.957(7) 163(9) 1_565
O6 H6B N7 0.80(9) 1.94(9) 2.736(6) 170(8) .
O7 H7A O1 0.84(9) 2.08(10) 2.895(6) 161(8) 2_766
O7 H7B N5 0.71(8) 2.13(8) 2.837(7) 175(8) 2_667
O8 H8A N3 0.89(6) 1.91(6) 2.790(7) 169(6) 1_456
O8 H8B O4 0.66(7) 2.45(7) 3.049(7) 154(7) 2_666

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
Ni1 O1 C1 N1 19.7(9) . . . . ?
Ni1 O1 C1 N3 -160.2(4) . . . . ?
C1 N1 C2 N2 179.5(6) . . . . ?
C1 N1 C2 N4 -0.5(9) . . . . ?
C1 N3 C4 N4 1.7(9) . . . . ?
C1 N3 C4 N6 -179.0(6) . . . . ?
C2 N1 C1 O1 -175.9(6) . . . . ?
C2 N1 C1 N3 4.0(9) . . . . ?
C2 N2 C3 O2 -176.1(6) . . . . ?
C2 N2 C3 N5 5.7(9) . . . . ?
C2 N4 C4 N3 1.5(9) . . . . ?
C2 N4 C4 N6 -177.7(6) . . . . ?
C2 N4 C5 N5 -0.4(9) . . . . ?
C2 N4 C5 N7 -179.7(6) . . . . ?
C3 N2 C2 N1 -179.0(6) . . . . ?
C3 N2 C2 N4 1.0(9) . . . . ?
C3 N5 C5 N4 7.4(9) . . . . ?
C3 N5 C5 N7 -173.4(6) . . . . ?
C4 N3 C1 O1 175.3(6) . . . . ?
C4 N3 C1 N1 -4.6(9) . . . . ?
C4 N4 C2 N1 -2.1(9) . . . . ?
C4 N4 C2 N2 177.8(6) . . . . ?
C4 N4 C5 N5 178.0(6) . . . . ?
C4 N4 C5 N7 -1.3(9) . . . . ?
C4 N6 C6 O3 176.2(6) . . . . ?
C4 N6 C6 N7 -3.1(10) . . . . ?
C5 N4 C2 N1 176.3(6) . . . . ?
C5 N4 C2 N2 -3.7(8) . . . . ?
C5 N4 C4 N3 -176.9(6) . . . . ?
C5 N4 C4 N6 3.8(9) . . . . ?
C5 N5 C3 O2 172.1(6) . . . . ?
C5 N5 C3 N2 -9.8(9) . . . . ?
C5 N7 C6 O3 -173.6(6) . . . . ?
C5 N7 C6 N6 5.7(9) . . . . ?
C6 N6 C4 N3 179.1(6) . . . . ?
C6 N6 C4 N4 -1.6(9) . . . . ?
C6 N7 C5 N4 -3.4(9) . . . . ?
C6 N7 C5 N5 177.4(6) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ada115
_database_code_depnum_ccdc_archive 'CCDC 1867181'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;University of Montreal
Canada
;
_audit_update_record             
;
2018-09-11 deposited with the CCDC.	2019-04-15 downloaded from the CCDC.
;
_audit_creation_date             2017-01-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C12 H10 N14 Ni0.49 O10 Zn0.51, H12 Ni0.92 O6 Zn0.08'
_chemical_formula_sum            'C12 H22 N14 Ni1.41 O16 Zn0.59'
_chemical_formula_weight         739.78
_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 0.0140 0.0070 '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 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -1.3360 3.2900 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0390 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -2.7480 0.5280 '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                   7.3891(3)
_cell_length_b                   8.6307(3)
_cell_length_c                   9.1887(4)
_cell_angle_alpha                77.928(2)
_cell_angle_beta                 84.470(2)
_cell_angle_gamma                87.086(2)
_cell_volume                     570.08(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    100
_cell_measurement_theta_max      60.694
_cell_measurement_theta_min      4.298
_shelx_estimated_absorpt_T_max   0.660
_shelx_estimated_absorpt_T_min   0.440
_exptl_absorpt_coefficient_mu    7.566
_exptl_absorpt_correction_T_max  0.2103
_exptl_absorpt_correction_T_min  0.1085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1446 before and 0.0768 after correction.
The Ratio of minimum to maximum transmission is 0.5159.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.155
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             377
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16725
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.650
_diffrn_reflns_theta_min         4.297
_diffrn_ambient_temperature      100
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2319
_reflns_number_total             2583
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.791
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.115
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2583
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.158
_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)+(0.0376P)²+2.0003P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1148
_refine_special_details          ?
_olex2_refinement_description    
;
1. Shared sites
{Ni1, Zn1}
{Ni2, Zn2}
2. Uiso/Uaniso restraints and constraints
Uanis(Ni1) = Uanis(Zn1)
Uanis(Ni2) = Uanis(Zn2)
3. Others
 Sof(Ni1)=0.5*(1-FVAR(2))
 Sof(Zn1)=0.5*FVAR(2)
 Sof(Zn2)=0.5*(1-FVAR(3))
 Sof(Ni2)=0.5*FVAR(3)
;
_atom_sites_solution_hydrogens   difmap
_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
Zn1 Zn 1.000000 0.000000 0.000000 0.0126(2) Uani 0.51(4) 2 d S T P . .
Ni1 Ni 1.000000 0.000000 0.000000 0.0126(2) Uani 0.49(4) 2 d S T P . .
N1 N 0.8867(4) 0.1267(3) 0.3095(3) 0.0156(6) Uani 1 1 d . . . . .
O1 O 1.0473(3) 0.2042(3) 0.0856(3) 0.0150(5) Uani 1 1 d . . . . .
C1 C 0.9713(4) 0.2435(4) 0.2005(4) 0.0136(6) Uani 1 1 d . . . . .
N2 N 0.9737(4) 0.3964(3) 0.2169(3) 0.0150(6) Uani 1 1 d . . . . .
O2 O 0.5482(3) -0.0051(3) 0.7564(3) 0.0174(5) Uani 1 1 d . . . . .
C2 C 0.7988(4) 0.1699(4) 0.4245(4) 0.0133(6) Uani 1 1 d . . . . .
C3 C 0.8812(4) 0.4378(4) 0.3352(4) 0.0133(6) Uani 1 1 d . . . . .
O3 O 0.7839(4) 0.7621(3) 0.4961(3) 0.0186(5) Uani 1 1 d . . . . .
N3 N 0.7116(4) 0.0633(3) 0.5343(3) 0.0157(6) Uani 1 1 d . . . . .
H3 H 0.724(6) -0.033(6) 0.529(5) 0.021(11) Uiso 1 1 d . . . . .
C4 C 0.6122(4) 0.1046(4) 0.6581(4) 0.0147(6) Uani 1 1 d . . . . .
N4 N 0.7875(4) 0.3236(3) 0.4434(3) 0.0139(6) Uani 1 1 d . . . . .
N5 N 0.8765(4) 0.5856(3) 0.3534(3) 0.0157(6) Uani 1 1 d . . . . .
C5 C 0.6827(4) 0.3674(4) 0.5657(4) 0.0129(6) Uani 1 1 d . . . . .
C6 C 0.7789(5) 0.6249(4) 0.4762(4) 0.0148(6) Uani 1 1 d . . . . .
N6 N 0.5907(4) 0.2581(3) 0.6667(3) 0.0151(6) Uani 1 1 d . . . . .
N7 N 0.6760(4) 0.5166(3) 0.5782(3) 0.0152(6) Uani 1 1 d . . . . .
O4 O 0.7222(3) 0.0530(3) 0.0182(3) 0.0169(5) Uani 1 1 d . . . . .
H4A H 0.654(7) 0.034(6) 0.092(6) 0.028(13) Uiso 1 1 d . . . . .
H4B H 0.661(7) 0.027(6) -0.049(6) 0.041(15) Uiso 1 1 d . . . . .
O5 O 0.9891(3) 0.1350(3) -0.2078(3) 0.0161(5) Uani 1 1 d . . . . .
H5A H 1.029(8) 0.074(7) -0.276(7) 0.048(16) Uiso 1 1 d . . . . .
H5B H 1.024(8) 0.220(8) -0.234(7) 0.051(18) Uiso 1 1 d . . . . .
Ni2 Ni 0.500000 0.500000 1.000000 0.0126(2) Uani 0.92(4) 2 d S T P . .
Zn2 Zn 0.500000 0.500000 1.000000 0.0126(2) Uani 0.08(4) 2 d S T P . .
O6 O 0.3875(4) 0.3212(3) 0.9264(3) 0.0182(5) Uani 1 1 d . . . . .
H6A H 0.428(6) 0.302(5) 0.846(5) 0.019(11) Uiso 1 1 d . . . . .
H6B H 0.279(7) 0.302(6) 0.940(6) 0.029(13) Uiso 1 1 d . . . . .
O7 O 0.4908(3) 0.6535(3) 0.7932(3) 0.0156(5) Uani 1 1 d . . . . .
H7A H 0.546(7) 0.612(6) 0.724(6) 0.031(13) Uiso 1 1 d . . . . .
H7B H 0.522(7) 0.745(7) 0.783(6) 0.037(15) Uiso 1 1 d . . . . .
O8 O 0.2555(3) 0.5897(3) 1.0719(3) 0.0177(5) Uani 1 1 d . . . . .
H8A H 0.165(7) 0.545(6) 1.114(6) 0.026(12) Uiso 1 1 d . . . . .
H8B H 0.230(7) 0.683(7) 1.059(6) 0.028(13) Uiso 1 1 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
Ni1 O1 2.132(2) 2_755 ?
Ni1 O1 2.132(2) . ?
Ni1 O4 2.079(2) 2_755 ?
Ni1 O4 2.079(2) . ?
Ni1 O5 2.025(2) . ?
Ni1 O5 2.024(2) 2_755 ?
N1 C1 1.390(4) . ?
N1 C2 1.299(4) . ?
O1 C1 1.249(4) . ?
C1 N2 1.360(4) . ?
N2 C3 1.331(4) . ?
O2 C4 1.241(4) . ?
C2 N3 1.351(5) . ?
C2 N4 1.370(4) . ?
C3 N4 1.402(4) . ?
C3 N5 1.319(4) . ?
O3 C6 1.238(4) . ?
N3 H3 0.84(5) . ?
N3 C4 1.394(4) . ?
C4 N6 1.344(4) . ?
N4 C5 1.410(4) . ?
N5 C6 1.373(4) . ?
C5 N6 1.338(4) . ?
C5 N7 1.314(4) . ?
C6 N7 1.378(4) . ?
O4 H4A 0.80(6) . ?
O4 H4B 0.88(6) . ?
O5 H5A 0.92(6) . ?
O5 H5B 0.77(7) . ?
Ni2 O6 2.051(3) . ?
Ni2 O6 2.051(3) 2_667 ?
Ni2 O7 2.082(2) 2_667 ?
Ni2 O7 2.082(2) . ?
Ni2 O8 2.035(2) 2_667 ?
Ni2 O8 2.035(2) . ?
O6 H6A 0.82(5) . ?
O6 H6B 0.82(5) . ?
O7 H7A 0.85(5) . ?
O7 H7B 0.82(6) . ?
O8 H8A 0.81(5) . ?
O8 H8B 0.81(5) . ?

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 O1 180.0 . 2_755 ?
O4 Ni1 O1 89.59(10) 2_755 2_755 ?
O4 Ni1 O1 90.41(10) . 2_755 ?
O4 Ni1 O1 90.41(10) 2_755 . ?
O4 Ni1 O1 89.59(10) . . ?
O4 Ni1 O4 180.0 2_755 . ?
O5 Ni1 O1 89.38(10) . 2_755 ?
O5 Ni1 O1 89.38(10) 2_755 . ?
O5 Ni1 O1 90.62(10) 2_755 2_755 ?
O5 Ni1 O1 90.62(10) . . ?
O5 Ni1 O4 83.31(10) . . ?
O5 Ni1 O4 96.69(10) . 2_755 ?
O5 Ni1 O4 83.31(10) 2_755 2_755 ?
O5 Ni1 O4 96.69(10) 2_755 . ?
O5 Ni1 O5 180.0 2_755 . ?
C2 N1 C1 117.7(3) . . ?
C1 O1 Ni1 127.6(2) . . ?
O1 C1 N1 118.0(3) . . ?
O1 C1 N2 120.2(3) . . ?
N2 C1 N1 121.8(3) . . ?
C3 N2 C1 119.1(3) . . ?
N1 C2 N3 121.1(3) . . ?
N1 C2 N4 123.2(3) . . ?
N3 C2 N4 115.7(3) . . ?
N2 C3 N4 120.1(3) . . ?
N5 C3 N2 121.0(3) . . ?
N5 C3 N4 118.9(3) . . ?
C2 N3 H3 118(3) . . ?
C2 N3 C4 123.1(3) . . ?
C4 N3 H3 119(3) . . ?
O2 C4 N3 117.2(3) . . ?
O2 C4 N6 123.2(3) . . ?
N6 C4 N3 119.5(3) . . ?
C2 N4 C3 117.9(3) . . ?
C2 N4 C5 121.6(3) . . ?
C3 N4 C5 120.5(3) . . ?
C3 N5 C6 119.7(3) . . ?
N6 C5 N4 120.0(3) . . ?
N7 C5 N4 119.1(3) . . ?
N7 C5 N6 120.8(3) . . ?
O3 C6 N5 118.9(3) . . ?
O3 C6 N7 118.9(3) . . ?
N5 C6 N7 122.2(3) . . ?
C5 N6 C4 119.5(3) . . ?
C5 N7 C6 119.4(3) . . ?
Ni1 O4 H4A 127(4) . . ?
Ni1 O4 H4B 116(4) . . ?
H4A O4 H4B 103(5) . . ?
Ni1 O5 H5A 108(4) . . ?
Ni1 O5 H5B 126(5) . . ?
H5A O5 H5B 110(6) . . ?
O6 Ni2 O6 180.0 2_667 . ?
O6 Ni2 O7 92.29(10) . . ?
O6 Ni2 O7 87.71(10) . 2_667 ?
O6 Ni2 O7 92.29(10) 2_667 2_667 ?
O6 Ni2 O7 87.71(10) 2_667 . ?
O7 Ni2 O7 180.00(19) . 2_667 ?
O8 Ni2 O6 86.04(11) . 2_667 ?
O8 Ni2 O6 86.04(11) 2_667 . ?
O8 Ni2 O6 93.96(11) . . ?
O8 Ni2 O6 93.96(11) 2_667 2_667 ?
O8 Ni2 O7 90.40(10) . . ?
O8 Ni2 O7 89.60(10) 2_667 . ?
O8 Ni2 O7 89.60(10) . 2_667 ?
O8 Ni2 O7 90.40(10) 2_667 2_667 ?
O8 Ni2 O8 180.0 2_667 . ?
Ni2 O6 H6A 119(3) . . ?
Ni2 O6 H6B 124(3) . . ?
H6A O6 H6B 109(5) . . ?
Ni2 O7 H7A 111(3) . . ?
Ni2 O7 H7B 119(4) . . ?
H7A O7 H7B 110(5) . . ?
Ni2 O8 H8A 130(3) . . ?
Ni2 O8 H8B 124(4) . . ?
H8A O8 H8B 106(5) . . ?

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
N3 H3 O3 0.84(5) 1.88(5) 2.715(4) 171(4) 1_545
O4 H4A O2 0.80(6) 1.93(6) 2.717(4) 168(5) 2_656
O4 H4B O2 0.88(6) 2.11(6) 2.977(4) 168(5) 1_554
O5 H5A N1 0.92(6) 1.89(6) 2.706(4) 148(5) 2_755
O5 H5B O3 0.77(7) 2.65(6) 2.989(3) 108(5) 2_765
O5 H5B N5 0.77(7) 1.94(7) 2.689(4) 164(6) 2_765
O6 H6A N6 0.82(5) 2.03(5) 2.831(4) 165(4) .
O6 H6B O1 0.82(5) 2.16(6) 2.900(4) 150(5) 1_456
O7 H7A N7 0.85(5) 1.88(6) 2.731(4) 177(5) .
O7 H7B O2 0.82(6) 2.14(6) 2.943(4) 169(5) 1_565
O8 H8A N2 0.81(5) 1.99(6) 2.790(4) 169(5) 1_456
O8 H8B O1 0.81(5) 2.58(5) 3.067(3) 120(4) 2_666
O8 H8B O4 0.81(5) 2.27(6) 3.030(4) 156(5) 2_666
O8 H8B O5 0.81(5) 2.68(5) 3.293(4) 134(4) 2_666

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
Ni1 O1 C1 N1 20.5(4) . . . . ?
Ni1 O1 C1 N2 -159.9(2) . . . . ?
N1 C1 N2 C3 -5.1(5) . . . . ?
N1 C2 N3 C4 -178.5(3) . . . . ?
N1 C2 N4 C3 -2.3(5) . . . . ?
N1 C2 N4 C5 176.5(3) . . . . ?
O1 C1 N2 C3 175.4(3) . . . . ?
C1 N1 C2 N3 179.3(3) . . . . ?
C1 N1 C2 N4 -0.6(5) . . . . ?
C1 N2 C3 N4 2.0(5) . . . . ?
C1 N2 C3 N5 -178.4(3) . . . . ?
N2 C3 N4 C2 1.6(5) . . . . ?
N2 C3 N4 C5 -177.3(3) . . . . ?
N2 C3 N5 C6 179.6(3) . . . . ?
O2 C4 N6 C5 171.6(3) . . . . ?
C2 N1 C1 O1 -176.0(3) . . . . ?
C2 N1 C1 N2 4.4(5) . . . . ?
C2 N3 C4 O2 -175.3(3) . . . . ?
C2 N3 C4 N6 4.3(5) . . . . ?
C2 N4 C5 N6 -0.2(5) . . . . ?
C2 N4 C5 N7 -179.8(3) . . . . ?
C3 N4 C5 N6 178.6(3) . . . . ?
C3 N4 C5 N7 -0.9(4) . . . . ?
C3 N5 C6 O3 176.1(3) . . . . ?
C3 N5 C6 N7 -3.8(5) . . . . ?
O3 C6 N7 C5 -173.9(3) . . . . ?
N3 C2 N4 C3 177.8(3) . . . . ?
N3 C2 N4 C5 -3.4(4) . . . . ?
N3 C4 N6 C5 -8.0(5) . . . . ?
N4 C2 N3 C4 1.4(5) . . . . ?
N4 C3 N5 C6 -0.8(5) . . . . ?
N4 C5 N6 C4 6.1(5) . . . . ?
N4 C5 N7 C6 -3.5(5) . . . . ?
N5 C3 N4 C2 -178.0(3) . . . . ?
N5 C3 N4 C5 3.1(5) . . . . ?
N5 C6 N7 C5 6.0(5) . . . . ?
N6 C5 N7 C6 177.0(3) . . . . ?
N7 C5 N6 C4 -174.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_adam832
_database_code_depnum_ccdc_archive 'CCDC 1866133'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;University of Montreal
Canada
;
_audit_update_record             
;
2018-09-05 deposited with the CCDC.	2019-04-15 downloaded from the CCDC.
;
_audit_creation_date             2016-06-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 Mn N14 O10, H12 Mn O6'
_chemical_formula_sum            'C12 H22 Mn2 N14 O16'
_chemical_formula_weight         728.31
_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 0.0140 0.0070 '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 0.0240 0.0130 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0390 0.0240 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn -0.0160 2.2330 '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                   6.9844(4)
_cell_length_b                   8.7175(5)
_cell_length_c                   10.0198(6)
_cell_angle_alpha                79.079(2)
_cell_angle_beta                 81.581(2)
_cell_angle_gamma                84.507(2)
_cell_volume                     591.11(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9185
_cell_measurement_temperature    100
_cell_measurement_theta_max      60.593
_cell_measurement_theta_min      3.945
_shelx_estimated_absorpt_T_max   0.691
_shelx_estimated_absorpt_T_min   0.502
_exptl_absorpt_coefficient_mu    6.655
_exptl_absorpt_correction_T_max  0.5163
_exptl_absorpt_correction_T_min  0.4035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0923 before and 0.0415 after correction.
The Ratio of minimum to maximum transmission is 0.7815.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.046
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             370
_exptl_crystal_recrystallization_method 'crystallized in H2O'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            32337
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.579
_diffrn_reflns_theta_min         3.943
_diffrn_ambient_temperature      100
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2632
_reflns_number_total             2698
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
SAINT (2013) V8.37A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2013) V8.37A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         2698
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0215
_refine_ls_restrained_S_all      1.115
_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)+(0.0406P)²+0.1739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0633
_refine_ls_wR_factor_ref         0.0639
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_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
Mn1 Mn 0.5000 1.0000 1.0000 0.00995(8) Uani 1 2 d S T P . .
Mn2 Mn 1.0000 0.5000 0.0000 0.01070(8) Uani 1 2 d S T P . .
O1 O 0.46138(12) 0.80124(9) 0.89871(8) 0.01267(17) Uani 1 1 d . . . . .
O2 O 0.96215(12) 1.01445(9) 0.26334(8) 0.01676(17) Uani 1 1 d . . . . .
O3 O 0.73348(12) 0.25525(8) 0.49011(8) 0.01564(19) Uani 1 1 d . . . . .
O4 O 0.19481(12) 1.05935(10) 1.02310(9) 0.01596(18) Uani 1 1 d . . . . .
H4A H 0.136(3) 1.131(3) 0.978(2) 0.038(5) Uiso 1 1 d . . . . .
H4B H 0.127(3) 1.033(2) 1.099(2) 0.030(5) Uiso 1 1 d . . . . .
O5 O 0.54894(15) 1.14836(11) 0.80302(9) 0.0194(2) Uani 1 1 d . . . . .
H5A H 0.562(3) 1.239(3) 0.762(2) 0.031(5) Uiso 1 1 d . . . . .
H5B H 0.575(3) 1.095(3) 0.746(2) 0.036(5) Uiso 1 1 d . . . . .
O6 O 0.99813(13) 0.34900(10) 0.20091(9) 0.01371(17) Uani 1 1 d . . . . .
H6A H 0.965(3) 0.262(3) 0.224(2) 0.030(5) Uiso 1 1 d . . . . .
H6B H 0.947(3) 0.394(3) 0.259(2) 0.029(5) Uiso 1 1 d . . . . .
O7 O 1.08720(13) 0.69474(10) 0.08185(9) 0.01566(18) Uani 1 1 d . . . . .
H7A H 1.034(3) 0.709(2) 0.176(2) 0.043(6) Uiso 1 1 d . . . . .
H7B H 1.196(3) 0.732(2) 0.048(2) 0.043(5) Uiso 1 1 d . . . . .
O8 O 1.29264(12) 0.42040(10) -0.06330(9) 0.01479(17) Uani 1 1 d . . . . .
H8A H 1.365(3) 0.361(2) -0.011(2) 0.031(5) Uiso 1 1 d . . . . .
H8B H 1.371(3) 0.478(2) -0.118(2) 0.026(5) Uiso 1 1 d . . . . .
N1 N 0.60849(13) 0.88410(10) 0.68198(9) 0.01225(18) Uani 1 1 d . . . . .
N2 N 0.78302(13) 0.94690(10) 0.46787(9) 0.01260(18) Uani 1 1 d . . . . .
H2 H 0.767(2) 1.059(2) 0.4793(17) 0.022(4) Uiso 1 1 d . . . . .
N3 N 0.53536(13) 0.61635(10) 0.76581(9) 0.01195(18) Uani 1 1 d . . . . .
N4 N 0.71745(13) 0.68885(10) 0.54887(9) 0.01037(18) Uani 1 1 d . . . . .
N5 N 0.90579(13) 0.75580(10) 0.33126(9) 0.01241(18) Uani 1 1 d . . . . .
N6 N 0.63481(14) 0.42894(10) 0.63154(9) 0.01253(18) Uani 1 1 d . . . . .
N7 N 0.82845(13) 0.50011(11) 0.41101(9) 0.01214(18) Uani 1 1 d . . . . .
C1 C 0.53315(15) 0.76690(12) 0.78389(11) 0.0111(2) Uani 1 1 d . . . . .
C2 C 0.69901(16) 0.84132(13) 0.57027(11) 0.0099(2) Uani 1 1 d . . . . .
C3 C 0.88799(16) 0.90749(13) 0.34836(12) 0.0113(2) Uani 1 1 d . . . . .
C4 C 0.62761(16) 0.57514(13) 0.65080(11) 0.0099(2) Uani 1 1 d . . . . .
C5 C 0.81903(16) 0.64703(13) 0.42726(11) 0.0099(2) Uani 1 1 d . . . . .
C6 C 0.73246(16) 0.39189(12) 0.51086(11) 0.0117(2) Uani 1 1 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
Mn1 O1 2.2228(8) . ?
Mn1 O1 2.2228(8) 2_677 ?
Mn1 O4 2.1342(9) 2_677 ?
Mn1 O4 2.1342(9) . ?
Mn1 O5 2.1459(9) 2_677 ?
Mn1 O5 2.1459(9) . ?
Mn2 O6 2.1856(9) . ?
Mn2 O6 2.1856(9) 2_765 ?
Mn2 O7 2.1903(8) . ?
Mn2 O7 2.1903(8) 2_765 ?
Mn2 O8 2.1394(9) . ?
Mn2 O8 2.1394(9) 2_765 ?
O1 C1 1.2639(14) . ?
O2 C3 1.2352(14) . ?
O3 C6 1.2466(13) . ?
O4 H4A 0.81(2) . ?
O4 H4B 0.84(2) . ?
O5 H5A 0.82(2) . ?
O5 H5B 0.79(2) . ?
O6 H6A 0.80(2) . ?
O6 H6B 0.79(2) . ?
O7 H7A 0.99(2) . ?
O7 H7B 0.85(2) . ?
O8 H8A 0.85(2) . ?
O8 H8B 0.84(2) . ?
N1 C1 1.3833(13) . ?
N1 C2 1.3029(15) . ?
N2 H2 1.001(17) . ?
N2 C2 1.3467(14) . ?
N2 C3 1.3929(14) . ?
N3 C1 1.3567(13) . ?
N3 C4 1.3294(15) . ?
N4 C2 1.3770(14) . ?
N4 C4 1.4026(14) . ?
N4 C5 1.4095(14) . ?
N5 C3 1.3571(14) . ?
N5 C5 1.3361(14) . ?
N6 C4 1.3200(14) . ?
N6 C6 1.3769(14) . ?
N7 C5 1.3156(14) . ?
N7 C6 1.3811(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Mn1 O1 180.0 2_677 . ?
O4 Mn1 O1 88.99(3) . 2_677 ?
O4 Mn1 O1 91.02(3) 2_677 2_677 ?
O4 Mn1 O1 91.01(3) . . ?
O4 Mn1 O1 88.99(3) 2_677 . ?
O4 Mn1 O4 180.0 . 2_677 ?
O4 Mn1 O5 93.41(4) 2_677 2_677 ?
O4 Mn1 O5 93.41(4) . . ?
O4 Mn1 O5 86.59(4) 2_677 . ?
O4 Mn1 O5 86.59(4) . 2_677 ?
O5 Mn1 O1 89.92(3) . . ?
O5 Mn1 O1 90.08(3) 2_677 . ?
O5 Mn1 O1 89.92(3) 2_677 2_677 ?
O5 Mn1 O1 90.08(3) . 2_677 ?
O5 Mn1 O5 180.0 . 2_677 ?
O6 Mn2 O6 180.0 . 2_765 ?
O6 Mn2 O7 89.41(3) . 2_765 ?
O6 Mn2 O7 90.59(3) . . ?
O6 Mn2 O7 90.59(3) 2_765 2_765 ?
O6 Mn2 O7 89.41(3) 2_765 . ?
O7 Mn2 O7 180.0 . 2_765 ?
O8 Mn2 O6 88.17(3) . 2_765 ?
O8 Mn2 O6 91.83(3) 2_765 2_765 ?
O8 Mn2 O6 88.17(3) 2_765 . ?
O8 Mn2 O6 91.83(3) . . ?
O8 Mn2 O7 93.48(3) 2_765 2_765 ?
O8 Mn2 O7 86.52(3) . 2_765 ?
O8 Mn2 O7 93.48(3) . . ?
O8 Mn2 O7 86.52(3) 2_765 . ?
O8 Mn2 O8 180.0 2_765 . ?
C1 O1 Mn1 132.06(7) . . ?
Mn1 O4 H4A 127.7(15) . . ?
Mn1 O4 H4B 120.1(14) . . ?
H4A O4 H4B 108(2) . . ?
Mn1 O5 H5A 145.5(14) . . ?
Mn1 O5 H5B 108.5(16) . . ?
H5A O5 H5B 106(2) . . ?
Mn2 O6 H6A 128.2(15) . . ?
Mn2 O6 H6B 110.3(15) . . ?
H6A O6 H6B 105(2) . . ?
Mn2 O7 H7A 119.4(12) . . ?
Mn2 O7 H7B 118.5(14) . . ?
H7A O7 H7B 117.3(18) . . ?
Mn2 O8 H8A 124.3(13) . . ?
Mn2 O8 H8B 122.7(13) . . ?
H8A O8 H8B 103.9(18) . . ?
C2 N1 C1 116.79(9) . . ?
C2 N2 H2 117.3(10) . . ?
C2 N2 C3 123.41(10) . . ?
C3 N2 H2 119.2(10) . . ?
C4 N3 C1 119.49(9) . . ?
C2 N4 C4 118.02(9) . . ?
C2 N4 C5 121.66(9) . . ?
C4 N4 C5 120.30(9) . . ?
C5 N5 C3 119.82(10) . . ?
C4 N6 C6 118.61(10) . . ?
C5 N7 C6 119.31(10) . . ?
O1 C1 N1 118.65(9) . . ?
O1 C1 N3 118.80(9) . . ?
N3 C1 N1 122.55(10) . . ?
N1 C2 N2 120.75(10) . . ?
N1 C2 N4 123.42(10) . . ?
N2 C2 N4 115.83(10) . . ?
O2 C3 N2 117.32(10) . . ?
O2 C3 N5 123.39(10) . . ?
N5 C3 N2 119.29(10) . . ?
N3 C4 N4 119.41(10) . . ?
N6 C4 N3 120.74(10) . . ?
N6 C4 N4 119.85(10) . . ?
N5 C5 N4 119.91(10) . . ?
N7 C5 N4 119.07(10) . . ?
N7 C5 N5 121.02(10) . . ?
O3 C6 N6 118.79(10) . . ?
O3 C6 N7 118.43(10) . . ?
N6 C6 N7 122.78(10) . . ?

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
O4 H4B O2 0.84(2) 1.85(2) 2.6846(12) 170(2) 1_456
O5 H5A N6 0.82(2) 1.97(2) 2.7715(13) 166(2) 1_565
O5 H5B N1 0.79(2) 2.04(2) 2.7709(13) 153(2) .
O6 H6A O2 0.80(2) 2.12(2) 2.8919(12) 163(2) 1_545
O6 H6B N7 0.79(2) 1.97(2) 2.7555(13) 177(2) .
O7 H7A N5 0.99(2) 1.77(2) 2.7534(13) 169.8(18) .
O7 H7B O1 0.85(2) 2.26(2) 3.0780(12) 160.8(19) 1_654
O8 H8B N3 0.84(2) 1.86(2) 2.7055(12) 176.0(19) 1_654
N2 H2 O3 1.001(17) 1.724(17) 2.7242(11) 176.7(15) 1_565

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
Mn1 O1 C1 N1 -20.54(15) . . . . ?
Mn1 O1 C1 N3 158.72(7) . . . . ?
C1 N1 C2 N2 -177.54(9) . . . . ?
C1 N1 C2 N4 1.78(16) . . . . ?
C1 N3 C4 N4 -1.39(16) . . . . ?
C1 N3 C4 N6 178.86(10) . . . . ?
C2 N1 C1 O1 173.09(10) . . . . ?
C2 N1 C1 N3 -6.14(16) . . . . ?
C2 N2 C3 O2 -178.28(10) . . . . ?
C2 N2 C3 N5 1.04(17) . . . . ?
C2 N4 C4 N3 -2.69(16) . . . . ?
C2 N4 C4 N6 177.07(9) . . . . ?
C2 N4 C5 N5 2.23(15) . . . . ?
C2 N4 C5 N7 -178.52(10) . . . . ?
C3 N2 C2 N1 177.47(10) . . . . ?
C3 N2 C2 N4 -1.90(16) . . . . ?
C3 N5 C5 N4 -3.12(16) . . . . ?
C3 N5 C5 N7 177.64(10) . . . . ?
C4 N3 C1 O1 -173.23(10) . . . . ?
C4 N3 C1 N1 5.99(16) . . . . ?
C4 N4 C2 N1 2.48(16) . . . . ?
C4 N4 C2 N2 -178.17(9) . . . . ?
C4 N4 C5 N5 -179.35(9) . . . . ?
C4 N4 C5 N7 -0.10(16) . . . . ?
C4 N6 C6 O3 -177.38(10) . . . . ?
C4 N6 C6 N7 2.14(16) . . . . ?
C5 N4 C2 N1 -179.06(11) . . . . ?
C5 N4 C2 N2 0.29(14) . . . . ?
C5 N4 C4 N3 178.83(9) . . . . ?
C5 N4 C4 N6 -1.41(16) . . . . ?
C5 N5 C3 O2 -179.13(10) . . . . ?
C5 N5 C3 N2 1.58(16) . . . . ?
C5 N7 C6 O3 175.85(10) . . . . ?
C5 N7 C6 N6 -3.66(16) . . . . ?
C6 N6 C4 N3 -179.86(10) . . . . ?
C6 N6 C4 N4 0.39(16) . . . . ?
C6 N7 C5 N4 2.51(15) . . . . ?
C6 N7 C5 N5 -178.25(9) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-05-18
_olex2_date_sample_submission    2016-05-16
_olex2_exptl_crystal_mounting_method 'mounted on a Mitegen Cryoloop'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_adam95
_database_code_depnum_ccdc_archive 'CCDC 1866132'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;University of Montreal
Canada
;
_audit_update_record             
;
2018-09-05 deposited with the CCDC.	2019-04-15 downloaded from the CCDC.
;
_audit_creation_date             2018-09-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 Co N14 O10, Co H12 O6'
_chemical_formula_sum            'C12 H22 Co2 N14 O16'
_chemical_formula_weight         736.29
_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 0.0140 0.0070 '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 -0.6630 2.9000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0240 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0390 0.0250 '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                   7.3633(3)
_cell_length_b                   8.6464(3)
_cell_length_c                   9.2763(3)
_cell_angle_alpha                77.947(2)
_cell_angle_beta                 84.247(2)
_cell_angle_gamma                87.228(2)
_cell_volume                     574.43(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    120
_cell_measurement_theta_max      60.688
_cell_measurement_theta_min      4.260
_shelx_estimated_absorpt_T_max   0.724
_shelx_estimated_absorpt_T_min   0.545
_exptl_absorpt_coefficient_mu    8.627
_exptl_absorpt_correction_T_max  0.3747
_exptl_absorpt_correction_T_min  0.2668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1129 before and 0.0753 after correction.
The Ratio of minimum to maximum transmission is 0.7120.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.128
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             374
_exptl_crystal_recrystallization_method 'in H2O'
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            30851
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.758
_diffrn_reflns_theta_min         4.258
_diffrn_ambient_temperature      120
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2457
_reflns_number_total             2633
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
SAINT (2013) V8.37A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2013) V8.37A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         2633
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0288
_refine_ls_restrained_S_all      1.098
_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)+(0.0431P)²+0.4726P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0786
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 N2-H2
 0.9 with sigma of 0.001
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_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 0.000000 0.000000 0.00896(10) Uani 1 2 d S T P . .
Co2 Co 0.000000 0.500000 1.000000 0.00933(10) Uani 1 2 d S T P . .
O1 O 0.54791(17) 0.20308(14) 0.08946(14) 0.0135(3) Uani 1 1 d . . . . .
O2 O 0.04851(18) -0.00721(15) 0.75728(14) 0.0190(3) Uani 1 1 d . . . . .
O3 O 0.28125(19) 0.75991(14) 0.49695(13) 0.0177(3) Uani 1 1 d . . . . .
O4 O 0.77928(17) -0.05415(16) -0.01647(16) 0.0162(3) Uani 1 1 d . . . . .
H4A H 0.846(4) -0.033(4) -0.090(4) 0.030(8) Uiso 1 1 d . . . . .
H4B H 0.844(4) -0.031(4) 0.056(4) 0.051(9) Uiso 1 1 d . . . . .
O5 O 0.50242(19) -0.13663(16) 0.20703(15) 0.0156(3) Uani 1 1 d . . . . .
H5A H 0.452(4) -0.078(4) 0.273(3) 0.035(8) Uiso 1 1 d . . . . .
H5B H 0.461(4) -0.236(4) 0.243(3) 0.036(8) Uiso 1 1 d . . . . .
O6 O -0.00497(18) 0.65376(16) 0.79280(15) 0.0142(3) Uani 1 1 d . . . . .
H6A H 0.030(4) 0.743(4) 0.781(3) 0.032(8) Uiso 1 1 d . . . . .
H6B H 0.054(4) 0.606(4) 0.719(3) 0.034(8) Uiso 1 1 d . . . . .
O7 O -0.11351(19) 0.31720(16) 0.92651(15) 0.0185(3) Uani 1 1 d . . . . .
H7A H -0.058(4) 0.298(3) 0.837(3) 0.025(6) Uiso 1 1 d . . . . .
H7B H -0.235(4) 0.287(4) 0.953(4) 0.050(9) Uiso 1 1 d . . . . .
O8 O -0.24887(18) 0.58929(16) 1.07015(15) 0.0177(3) Uani 1 1 d . . . . .
H8A H -0.343(4) 0.537(3) 1.107(3) 0.025(7) Uiso 1 1 d . . . . .
H8B H -0.277(5) 0.693(5) 1.056(4) 0.063(10) Uiso 1 1 d . . . . .
N1 N 0.3853(2) 0.12498(17) 0.31225(16) 0.0144(3) Uani 1 1 d . . . . .
N2 N 0.2115(2) 0.06118(17) 0.53601(16) 0.0148(3) Uani 1 1 d D . . . .
N3 N 0.4724(2) 0.39481(17) 0.22001(16) 0.0139(3) Uani 1 1 d . . . . .
N4 N 0.28643(19) 0.32168(17) 0.44532(16) 0.0121(3) Uani 1 1 d . . . . .
N5 N 0.0920(2) 0.25558(18) 0.66833(16) 0.0145(3) Uani 1 1 d . . . . .
N6 N 0.3754(2) 0.58355(17) 0.35532(16) 0.0143(3) Uani 1 1 d . . . . .
N7 N 0.1759(2) 0.51371(17) 0.57994(16) 0.0141(3) Uani 1 1 d . . . . .
C1 C 0.4703(2) 0.2421(2) 0.20424(19) 0.0125(3) Uani 1 1 d . . . . .
C2 C 0.2982(2) 0.1678(2) 0.42674(19) 0.0114(3) Uani 1 1 d . . . . .
C3 C 0.1136(2) 0.1017(2) 0.65882(19) 0.0130(3) Uani 1 1 d . . . . .
C4 C 0.3803(2) 0.4357(2) 0.33735(19) 0.0117(3) Uani 1 1 d . . . . .
C5 C 0.1824(2) 0.3650(2) 0.56727(19) 0.0107(3) Uani 1 1 d . . . . .
C6 C 0.2775(2) 0.6225(2) 0.47744(19) 0.0138(3) Uani 1 1 d . . . . .
H2 H 0.225(4) -0.0414(8) 0.530(3) 0.028(6) 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 O1 2.1502(12) 2_655 ?
Co1 O1 2.1502(12) . ?
Co1 O4 2.0846(13) 2_655 ?
Co1 O4 2.0845(13) . ?
Co1 O5 2.0351(13) . ?
Co1 O5 2.0351(13) 2_655 ?
Co2 O6 2.0989(13) 2_567 ?
Co2 O6 2.0989(13) . ?
Co2 O7 2.0865(13) 2_567 ?
Co2 O7 2.0865(13) . ?
Co2 O8 2.0522(13) 2_567 ?
Co2 O8 2.0522(13) . ?
O1 C1 1.258(2) . ?
O2 C3 1.244(2) . ?
O3 C6 1.241(2) . ?
O4 H4A 0.80(3) . ?
O4 H4B 0.92(4) . ?
O5 H5A 0.92(3) . ?
O5 H5B 0.91(3) . ?
O6 H6A 0.81(3) . ?
O6 H6B 0.93(3) . ?
O7 H7A 0.93(3) . ?
O7 H7B 0.94(3) . ?
O8 H8A 0.85(3) . ?
O8 H8B 0.90(4) . ?
N1 C1 1.390(2) . ?
N1 C2 1.297(2) . ?
N2 C2 1.350(2) . ?
N2 C3 1.385(2) . ?
N2 H2 0.9002(11) . ?
N3 C1 1.360(2) . ?
N3 C4 1.326(2) . ?
N4 C2 1.374(2) . ?
N4 C4 1.402(2) . ?
N4 C5 1.408(2) . ?
N5 C3 1.352(2) . ?
N5 C5 1.335(2) . ?
N6 C4 1.322(2) . ?
N6 C6 1.374(2) . ?
N7 C5 1.314(2) . ?
N7 C6 1.378(2) . ?

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 O1 180.0 . 2_655 ?
O4 Co1 O1 90.36(5) . . ?
O4 Co1 O1 89.64(5) 2_655 . ?
O4 Co1 O1 89.64(5) . 2_655 ?
O4 Co1 O1 90.36(5) 2_655 2_655 ?
O4 Co1 O4 180.0 . 2_655 ?
O5 Co1 O1 89.01(5) 2_655 2_655 ?
O5 Co1 O1 89.01(5) . . ?
O5 Co1 O1 90.99(5) 2_655 . ?
O5 Co1 O1 90.99(5) . 2_655 ?
O5 Co1 O4 95.74(5) 2_655 . ?
O5 Co1 O4 84.26(5) 2_655 2_655 ?
O5 Co1 O4 95.74(5) . 2_655 ?
O5 Co1 O4 84.26(5) . . ?
O5 Co1 O5 180.0 . 2_655 ?
O6 Co2 O6 180.0 . 2_567 ?
O7 Co2 O6 92.65(5) 2_567 2_567 ?
O7 Co2 O6 87.35(5) . 2_567 ?
O7 Co2 O6 92.65(5) . . ?
O7 Co2 O6 87.35(5) 2_567 . ?
O7 Co2 O7 180.0 2_567 . ?
O8 Co2 O6 90.73(5) . . ?
O8 Co2 O6 89.27(5) . 2_567 ?
O8 Co2 O6 89.27(5) 2_567 . ?
O8 Co2 O6 90.73(5) 2_567 2_567 ?
O8 Co2 O7 86.29(6) 2_567 . ?
O8 Co2 O7 93.71(6) 2_567 2_567 ?
O8 Co2 O7 86.29(6) . 2_567 ?
O8 Co2 O7 93.71(6) . . ?
O8 Co2 O8 180.0 . 2_567 ?
C1 O1 Co1 128.13(11) . . ?
Co1 O4 H4A 125(2) . . ?
Co1 O4 H4B 117(2) . . ?
H4A O4 H4B 104(3) . . ?
Co1 O5 H5A 107.9(19) . . ?
Co1 O5 H5B 129.8(19) . . ?
H5A O5 H5B 105(3) . . ?
Co2 O6 H6A 120(2) . . ?
Co2 O6 H6B 110.0(19) . . ?
H6A O6 H6B 109(3) . . ?
Co2 O7 H7A 114.2(16) . . ?
Co2 O7 H7B 122.9(19) . . ?
H7A O7 H7B 118(3) . . ?
Co2 O8 H8A 126.9(19) . . ?
Co2 O8 H8B 123(2) . . ?
H8A O8 H8B 110(3) . . ?
C2 N1 C1 117.51(15) . . ?
C2 N2 C3 123.12(15) . . ?
C2 N2 H2 117.3(16) . . ?
C3 N2 H2 119.5(16) . . ?
C4 N3 C1 119.01(15) . . ?
C2 N4 C4 117.73(14) . . ?
C2 N4 C5 121.57(14) . . ?
C4 N4 C5 120.69(15) . . ?
C5 N5 C3 119.27(15) . . ?
C4 N6 C6 119.61(15) . . ?
C5 N7 C6 119.33(15) . . ?
O1 C1 N1 118.02(15) . . ?
O1 C1 N3 119.92(15) . . ?
N3 C1 N1 122.07(15) . . ?
N1 C2 N2 121.04(16) . . ?
N1 C2 N4 123.23(16) . . ?
N2 C2 N4 115.73(15) . . ?
O2 C3 N2 117.75(16) . . ?
O2 C3 N5 122.43(16) . . ?
N5 C3 N2 119.82(16) . . ?
N3 C4 N4 120.28(15) . . ?
N6 C4 N3 120.97(16) . . ?
N6 C4 N4 118.75(15) . . ?
N5 C5 N4 120.08(15) . . ?
N7 C5 N4 119.16(15) . . ?
N7 C5 N5 120.76(16) . . ?
O3 C6 N6 119.04(16) . . ?
O3 C6 N7 118.68(16) . . ?
N6 C6 N7 122.28(15) . . ?

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
_geom_hbond_publ_flag
O4 H4A O2 0.80(3) 1.93(3) 2.7180(18) 167(3) 1_654 yes
O4 H4B O2 0.92(4) 2.07(4) 2.9798(19) 170(3) 2_656 yes
O5 H5A O3 0.92(3) 2.51(3) 2.9905(18) 113(2) 1_545 yes
O5 H5A N1 0.92(3) 1.90(3) 2.716(2) 148(3) . yes
O5 H5B N6 0.91(3) 1.79(3) 2.682(2) 166(3) 1_545 yes
O6 H6A O2 0.81(3) 2.13(3) 2.9221(19) 165(3) 1_565 yes
O6 H6B N7 0.93(3) 1.80(3) 2.730(2) 178(3) . yes
O7 H7A N5 0.93(3) 1.92(3) 2.835(2) 171(2) . yes
O7 H7B O1 0.94(3) 2.00(4) 2.8868(18) 157(3) 1_456 yes
O8 H8A N3 0.85(3) 1.95(3) 2.785(2) 169(3) 1_456 yes
O8 H8B O1 0.90(4) 2.55(4) 3.0700(18) 118(3) 2_566 yes
O8 H8B O4 0.90(4) 2.19(4) 3.031(2) 155(3) 1_466 yes
O8 H8B O5 0.90(4) 2.63(4) 3.3095(19) 133(3) 1_466 yes

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
Co1 O1 C1 N1 21.6(2) . . . . ?
Co1 O1 C1 N3 -158.79(12) . . . . ?
C1 N1 C2 N2 179.70(15) . . . . ?
C1 N1 C2 N4 0.1(3) . . . . ?
C1 N3 C4 N4 1.8(2) . . . . ?
C1 N3 C4 N6 -178.51(15) . . . . ?
C2 N1 C1 O1 -176.72(15) . . . . ?
C2 N1 C1 N3 3.7(2) . . . . ?
C2 N2 C3 O2 -175.66(16) . . . . ?
C2 N2 C3 N5 4.3(3) . . . . ?
C2 N4 C4 N3 1.8(2) . . . . ?
C2 N4 C4 N6 -177.95(15) . . . . ?
C2 N4 C5 N5 -0.1(2) . . . . ?
C2 N4 C5 N7 179.92(16) . . . . ?
C3 N2 C2 N1 -178.62(16) . . . . ?
C3 N2 C2 N4 1.0(2) . . . . ?
C3 N5 C5 N4 5.5(2) . . . . ?
C3 N5 C5 N7 -174.53(16) . . . . ?
C4 N3 C1 O1 175.82(15) . . . . ?
C4 N3 C1 N1 -4.6(2) . . . . ?
C4 N4 C2 N1 -2.7(2) . . . . ?
C4 N4 C2 N2 177.61(15) . . . . ?
C4 N4 C5 N5 179.19(15) . . . . ?
C4 N4 C5 N7 -0.8(2) . . . . ?
C4 N6 C6 O3 176.48(16) . . . . ?
C4 N6 C6 N7 -3.1(3) . . . . ?
C5 N4 C2 N1 176.54(17) . . . . ?
C5 N4 C2 N2 -3.1(2) . . . . ?
C5 N4 C4 N3 -177.51(15) . . . . ?
C5 N4 C4 N6 2.8(2) . . . . ?
C5 N5 C3 O2 172.44(16) . . . . ?
C5 N5 C3 N2 -7.5(2) . . . . ?
C5 N7 C6 O3 -174.50(16) . . . . ?
C5 N7 C6 N6 5.0(3) . . . . ?
C6 N6 C4 N3 179.45(15) . . . . ?
C6 N6 C4 N4 -0.8(2) . . . . ?
C6 N7 C5 N4 -3.0(2) . . . . ?
C6 N7 C5 N5 177.04(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_adam842
_database_code_depnum_ccdc_archive 'CCDC 1866131'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;University of Montreal
Canada
;
_audit_update_record             
;
2018-09-05 deposited with the CCDC.	2019-04-15 downloaded from the CCDC.
;
_audit_creation_date             2016-05-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 N14 O10 Zn, H12 O6 Zn'
_chemical_formula_sum            'C12 H22 N14 O16 Zn2'
_chemical_formula_weight         749.17
_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 0.0140 0.0070 '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 0.0240 0.0130 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0390 0.0240 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -2.7480 0.5280 '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                   7.4188(3)
_cell_length_b                   8.6369(4)
_cell_length_c                   9.2126(4)
_cell_angle_alpha                77.798(2)
_cell_angle_beta                 84.443(2)
_cell_angle_gamma                87.127(2)
_cell_volume                     573.99(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    100
_cell_measurement_theta_max      60.721
_cell_measurement_theta_min      4.290
_shelx_estimated_absorpt_T_max   0.890
_shelx_estimated_absorpt_T_min   0.673
_exptl_absorpt_coefficient_mu    2.388
_exptl_absorpt_correction_T_max  0.5163
_exptl_absorpt_correction_T_min  0.4064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1053 before and 0.0581 after correction.
The Ratio of minimum to maximum transmission is 0.7871.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.167
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       platelet
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            23186
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.763
_diffrn_reflns_theta_min         4.288
_diffrn_ambient_temperature      100
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2454
_reflns_number_total             2636
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
SAINT (2013) V8.37A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2013) V8.37A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         2636
_refine_ls_number_restraints     45
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0264
_refine_ls_restrained_S_all      1.067
_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)+(0.0460P)²+0.2171P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0719
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 O4-H4A \\sim O4-H4B \\sim O5-H5A \\sim O5-H5B \\sim O6-H6A \\sim O6-H6B \\sim
O7-H7A \\sim O7-H7B \\sim O8-
 H8A \\sim O8-H8B
 with sigma of 0.02
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_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
Zn1 Zn 0.5000 1.0000 1.0000 0.01144(10) Uani 1 2 d S T P . .
O1 O 0.45186(13) 0.79405(11) 0.91371(11) 0.0132(2) Uani 1 1 d . . . . .
O2 O 0.95112(14) 1.00457(11) 0.24416(11) 0.0159(2) Uani 1 1 d . . . . .
O3 O 0.71627(15) 0.23741(11) 0.50405(10) 0.0163(2) Uani 1 1 d . . . . .
O4 O 0.22023(14) 1.05387(12) 1.01847(11) 0.0152(2) Uani 1 1 d D . . . .
H4A H 0.162(4) 1.023(4) 1.095(2) 0.062(9) Uiso 1 1 d D . . . .
H4B H 0.170(3) 1.033(3) 0.951(2) 0.047(7) Uiso 1 1 d D . . . .
O5 O 0.48935(14) 1.13474(12) 0.79186(11) 0.0143(2) Uani 1 1 d D . . . .
H5A H 0.524(4) 1.224(2) 0.764(3) 0.043(7) Uiso 1 1 d D . . . .
H5B H 0.532(3) 1.081(2) 0.734(2) 0.032(6) Uiso 1 1 d D . . . .
N1 N 0.61291(16) 0.87229(13) 0.68999(13) 0.0132(2) Uani 1 1 d . . . . .
N2 N 0.78759(16) 0.93618(14) 0.46587(13) 0.0133(2) Uani 1 1 d . . . . .
H2 H 0.775(3) 1.039(3) 0.474(2) 0.036(6) Uiso 1 1 d . . . . .
N3 N 0.52651(15) 0.60239(13) 0.78246(13) 0.0127(2) Uani 1 1 d . . . . .
N4 N 0.71184(15) 0.67567(13) 0.55646(12) 0.0114(2) Uani 1 1 d . . . . .
N5 N 0.90864(16) 0.74142(13) 0.33410(12) 0.0133(2) Uani 1 1 d . . . . .
N6 N 0.62286(16) 0.41369(13) 0.64651(13) 0.0135(2) Uani 1 1 d . . . . .
N7 N 0.82373(16) 0.48330(13) 0.42224(13) 0.0130(2) Uani 1 1 d . . . . .
C1 C 0.52875(18) 0.75491(15) 0.79809(15) 0.0123(3) Uani 1 1 d . . . . .
C2 C 0.70112(18) 0.82942(16) 0.57507(15) 0.0116(3) Uani 1 1 d . . . . .
C3 C 0.88666(18) 0.89497(16) 0.34263(15) 0.0125(3) Uani 1 1 d . . . . .
C4 C 0.61864(18) 0.56123(16) 0.66469(15) 0.0114(3) Uani 1 1 d . . . . .
C5 C 0.81718(18) 0.63161(16) 0.43471(15) 0.0114(3) Uani 1 1 d . . . . .
C6 C 0.72104(18) 0.37460(16) 0.52402(15) 0.0130(3) Uani 1 1 d . . . . .
Zn2 Zn 1.0000 0.5000 0.0000 0.01154(10) Uani 1 2 d S T P . .
O6 O 1.00880(14) 0.34406(12) 0.20960(11) 0.0141(2) Uani 1 1 d D . . . .
H6A H 0.973(3) 0.2590(19) 0.217(2) 0.027(6) Uiso 1 1 d D . . . .
H6B H 0.959(3) 0.388(3) 0.271(2) 0.031(6) Uiso 1 1 d D . . . .
O7 O 1.11379(14) 0.68055(12) 0.07478(12) 0.0167(2) Uani 1 1 d D . . . .
H7A H 1.064(3) 0.694(3) 0.1532(18) 0.029(5) Uiso 1 1 d D . . . .
H7B H 1.220(2) 0.698(3) 0.058(3) 0.050(7) Uiso 1 1 d D . . . .
O8 O 1.24574(14) 0.41015(12) -0.07256(12) 0.0165(2) Uani 1 1 d D . . . .
H8A H 1.327(3) 0.463(3) -0.108(2) 0.033(6) Uiso 1 1 d D . . . .
H8B H 1.268(3) 0.3181(18) -0.055(3) 0.035(6) 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
Zn1 O1 2.1540(10) . ?
Zn1 O1 2.1540(10) 2_677 ?
Zn1 O4 2.1028(10) . ?
Zn1 O4 2.1028(10) 2_677 ?
Zn1 O5 2.0283(10) . ?
Zn1 O5 2.0283(10) 2_677 ?
O1 C1 1.2608(17) . ?
O2 C3 1.2434(17) . ?
O3 C6 1.2396(16) . ?
O4 H4A 0.792(16) . ?
O4 H4B 0.814(15) . ?
O5 H5A 0.805(15) . ?
O5 H5B 0.810(15) . ?
N1 C1 1.3877(17) . ?
N1 C2 1.3014(18) . ?
N2 H2 0.91(2) . ?
N2 C2 1.3476(18) . ?
N2 C3 1.3924(17) . ?
N3 C1 1.3561(17) . ?
N3 C4 1.3288(18) . ?
N4 C2 1.3719(17) . ?
N4 C4 1.4027(17) . ?
N4 C5 1.4123(17) . ?
N5 C3 1.3459(17) . ?
N5 C5 1.3379(17) . ?
N6 C4 1.3183(17) . ?
N6 C6 1.3767(17) . ?
N7 C5 1.3082(18) . ?
N7 C6 1.3792(17) . ?
Zn2 O6 2.1126(10) . ?
Zn2 O6 2.1126(10) 2_765 ?
Zn2 O7 2.0779(10) 2_765 ?
Zn2 O7 2.0779(10) . ?
Zn2 O8 2.0528(10) . ?
Zn2 O8 2.0529(10) 2_765 ?
O6 H6A 0.781(14) . ?
O6 H6B 0.795(15) . ?
O7 H7A 0.807(14) . ?
O7 H7B 0.808(15) . ?
O8 H8A 0.780(14) . ?
O8 H8B 0.790(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O1 180.0 2_677 . ?
O4 Zn1 O1 90.42(4) . . ?
O4 Zn1 O1 89.58(4) 2_677 . ?
O4 Zn1 O1 90.42(4) 2_677 2_677 ?
O4 Zn1 O1 89.58(4) . 2_677 ?
O4 Zn1 O4 180.000(13) . 2_677 ?
O5 Zn1 O1 89.13(4) . . ?
O5 Zn1 O1 89.13(4) 2_677 2_677 ?
O5 Zn1 O1 90.87(4) 2_677 . ?
O5 Zn1 O1 90.87(4) . 2_677 ?
O5 Zn1 O4 96.65(4) . 2_677 ?
O5 Zn1 O4 83.35(4) 2_677 2_677 ?
O5 Zn1 O4 96.65(4) 2_677 . ?
O5 Zn1 O4 83.35(4) . . ?
O5 Zn1 O5 180.0 2_677 . ?
C1 O1 Zn1 127.41(8) . . ?
Zn1 O4 H4A 119(2) . . ?
Zn1 O4 H4B 112.1(18) . . ?
H4A O4 H4B 109(3) . . ?
Zn1 O5 H5A 126.3(19) . . ?
Zn1 O5 H5B 106.8(16) . . ?
H5A O5 H5B 109(2) . . ?
C2 N1 C1 117.47(11) . . ?
C2 N2 H2 116.8(14) . . ?
C2 N2 C3 122.94(12) . . ?
C3 N2 H2 120.3(14) . . ?
C4 N3 C1 118.99(11) . . ?
C2 N4 C4 118.01(11) . . ?
C2 N4 C5 121.53(11) . . ?
C4 N4 C5 120.44(11) . . ?
C5 N5 C3 119.52(12) . . ?
C4 N6 C6 119.57(12) . . ?
C5 N7 C6 119.42(12) . . ?
O1 C1 N1 117.80(12) . . ?
O1 C1 N3 119.91(12) . . ?
N3 C1 N1 122.29(12) . . ?
N1 C2 N2 121.05(12) . . ?
N1 C2 N4 122.98(12) . . ?
N2 C2 N4 115.97(12) . . ?
O2 C3 N2 117.33(12) . . ?
O2 C3 N5 122.92(12) . . ?
N5 C3 N2 119.75(12) . . ?
N3 C4 N4 120.08(12) . . ?
N6 C4 N3 121.00(12) . . ?
N6 C4 N4 118.91(12) . . ?
N5 C5 N4 119.80(12) . . ?
N7 C5 N4 119.22(12) . . ?
N7 C5 N5 120.97(12) . . ?
O3 C6 N6 118.94(12) . . ?
O3 C6 N7 118.88(12) . . ?
N6 C6 N7 122.17(12) . . ?
O6 Zn2 O6 180.0 . 2_765 ?
O7 Zn2 O6 87.85(4) . 2_765 ?
O7 Zn2 O6 92.15(4) . . ?
O7 Zn2 O6 92.14(4) 2_765 2_765 ?
O7 Zn2 O6 87.85(4) 2_765 . ?
O7 Zn2 O7 180.0 . 2_765 ?
O8 Zn2 O6 90.55(4) . . ?
O8 Zn2 O6 90.56(4) 2_765 2_765 ?
O8 Zn2 O6 89.44(4) 2_765 . ?
O8 Zn2 O6 89.44(4) . 2_765 ?
O8 Zn2 O7 93.88(4) . . ?
O8 Zn2 O7 93.88(4) 2_765 2_765 ?
O8 Zn2 O7 86.12(4) . 2_765 ?
O8 Zn2 O7 86.12(4) 2_765 . ?
O8 Zn2 O8 180.0 . 2_765 ?
Zn2 O6 H6A 116.9(16) . . ?
Zn2 O6 H6B 107.8(17) . . ?
H6A O6 H6B 112(2) . . ?
Zn2 O7 H7A 111.8(15) . . ?
Zn2 O7 H7B 121.5(19) . . ?
H7A O7 H7B 118(2) . . ?
Zn2 O8 H8A 123.4(18) . . ?
Zn2 O8 H8B 121.3(17) . . ?
H8A O8 H8B 115(2) . . ?

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
O4 H4A O2 0.792(16) 1.971(19) 2.7198(14) 158(3) 1_456
O4 H4B O2 0.814(15) 2.172(15) 2.9835(15) 175(2) 2_676
O5 H5A N6 0.805(15) 1.900(16) 2.6828(15) 164(3) 1_565
O5 H5B O3 0.810(15) 2.57(2) 2.9903(14) 113.6(18) 1_565
O5 H5B N1 0.810(15) 1.980(17) 2.7173(15) 151(2) .
N2 H2 O3 0.91(2) 1.82(2) 2.7176(14) 171(2) 1_565
O6 H6A O2 0.781(14) 2.171(15) 2.9303(14) 164(2) 1_545
O6 H6B N7 0.795(15) 1.941(15) 2.7346(15) 176(2) .
O7 H7A N5 0.807(14) 2.035(14) 2.8367(15) 172(2) .
O7 H7B O1 0.808(15) 2.151(19) 2.8920(14) 153(3) 1_654
O8 H8A N3 0.780(14) 2.006(15) 2.7839(15) 175(2) 1_654
O8 H8B O1 0.790(15) 2.60(2) 3.0714(15) 120.4(19) 2_766
O8 H8B O4 0.790(15) 2.276(16) 3.0240(15) 158(2) 1_644

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
Zn1 O1 C1 N1 -20.67(17) . . . . ?
Zn1 O1 C1 N3 159.62(9) . . . . ?
C1 N1 C2 N2 -179.50(12) . . . . ?
C1 N1 C2 N4 0.8(2) . . . . ?
C1 N3 C4 N4 -1.92(19) . . . . ?
C1 N3 C4 N6 178.75(12) . . . . ?
C2 N1 C1 O1 176.03(12) . . . . ?
C2 N1 C1 N3 -4.3(2) . . . . ?
C2 N2 C3 O2 175.52(13) . . . . ?
C2 N2 C3 N5 -4.3(2) . . . . ?
C2 N4 C4 N3 -1.34(19) . . . . ?
C2 N4 C4 N6 178.01(12) . . . . ?
C2 N4 C5 N5 -0.28(19) . . . . ?
C2 N4 C5 N7 179.68(13) . . . . ?
C3 N2 C2 N1 178.61(13) . . . . ?
C3 N2 C2 N4 -1.7(2) . . . . ?
C3 N5 C5 N4 -5.85(19) . . . . ?
C3 N5 C5 N7 174.19(12) . . . . ?
C4 N3 C1 O1 -175.47(12) . . . . ?
C4 N3 C1 N1 4.8(2) . . . . ?
C4 N4 C2 N1 1.9(2) . . . . ?
C4 N4 C2 N2 -177.81(12) . . . . ?
C4 N4 C5 N5 -178.50(12) . . . . ?
C4 N4 C5 N7 1.47(19) . . . . ?
C4 N6 C6 O3 -176.25(12) . . . . ?
C4 N6 C6 N7 3.3(2) . . . . ?
C5 N4 C2 N1 -176.35(13) . . . . ?
C5 N4 C2 N2 3.93(18) . . . . ?
C5 N4 C4 N3 176.94(12) . . . . ?
C5 N4 C4 N6 -3.72(19) . . . . ?
C5 N5 C3 O2 -171.78(13) . . . . ?
C5 N5 C3 N2 8.1(2) . . . . ?
C5 N7 C6 O3 173.96(12) . . . . ?
C5 N7 C6 N6 -5.6(2) . . . . ?
C6 N6 C4 N3 -179.36(12) . . . . ?
C6 N6 C4 N4 1.30(19) . . . . ?
C6 N7 C5 N4 3.07(19) . . . . ?
C6 N7 C5 N5 -176.96(12) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-05-16
_olex2_date_sample_submission    2016-05-13
_olex2_submission_original_sample_id 'MID-1 '
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ada1042
_database_code_depnum_ccdc_archive 'CCDC 1867182'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;University of Montreal
Canada
;
_audit_update_record             
;
2018-09-11 deposited with the CCDC.	2019-04-15 downloaded from the CCDC.
;
_audit_creation_date             2016-08-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 Co0.74 Mn0.26 N14 O10, Co H12 O6'
_chemical_formula_sum            'C12 H22 Co1.74 Mn0.26 N14 O16'
_chemical_formula_weight         735.26
_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 0.0140 0.0070 '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 -0.6628 2.9049 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn -0.0162 2.2332 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0240 0.0130 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0390 0.0240 '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                   6.9999(2)
_cell_length_b                   8.6955(2)
_cell_length_c                   9.8777(3)
_cell_angle_alpha                78.7700(10)
_cell_angle_beta                 81.6070(10)
_cell_angle_gamma                85.0940(10)
_cell_volume                     582.39(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9830
_cell_measurement_temperature    120
_cell_measurement_theta_max      60.755
_cell_measurement_theta_min      4.006
_shelx_estimated_absorpt_T_max   0.636
_shelx_estimated_absorpt_T_min   0.437
_exptl_absorpt_coefficient_mu    8.280
_exptl_absorpt_correction_T_max  0.2626
_exptl_absorpt_correction_T_min  0.1546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1243 before and 0.0831 after correction.
The Ratio of minimum to maximum transmission is 0.5887.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light Brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    Brown
_exptl_crystal_density_diffrn    2.096
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             373
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            27640
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.724
_diffrn_reflns_theta_min         4.005
_diffrn_ambient_temperature      120
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2391
_reflns_number_total             2658
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
SAINT (2013) V8.37A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2013) V8.37A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         2658
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.006
_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)+(0.0853P)²+2.0381P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1462
_refine_special_details          ?
_olex2_refinement_description    
;
1. Shared sites
{Mn1, Co1}
2. Uiso/Uaniso restraints and constraints
Uanis(Mn1) = Uanis(Co1)
3. Others
 Sof(Mn1)=0.5*(1-FVAR(2))
 Sof(Co1)=0.5*FVAR(2)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_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 0.5000 1.0000 1.0000 0.0146(2) Uani 0.74(5) 2 d S T P . .
Mn1 Mn 0.5000 1.0000 1.0000 0.0146(2) Uani 0.26(5) 2 d S T P . .
O1 O 0.4614(4) 0.8006(3) 0.9015(3) 0.0185(5) Uani 1 1 d . . . . .
O2 O 0.9642(4) 1.0165(3) 0.2566(3) 0.0233(6) Uani 1 1 d . . . . .
O3 O 0.7337(4) 0.2540(3) 0.4909(3) 0.0220(6) Uani 1 1 d . . . . .
O4 O 0.2029(4) 1.0591(4) 1.0162(3) 0.0224(6) Uani 1 1 d . . . . .
H4A H 0.148(10) 1.126(9) 0.970(7) 0.06(2) Uiso 1 1 d . . . . .
H4B H 0.132(8) 1.040(6) 1.083(6) 0.031(14) Uiso 1 1 d . . . . .
O5 O 0.5457(5) 1.1455(3) 0.8030(3) 0.0261(7) Uani 1 1 d . . . . .
H5A H 0.554(8) 1.234(8) 0.767(6) 0.037(15) Uiso 1 1 d . . . . .
H5B H 0.581(8) 1.081(7) 0.743(6) 0.036(14) Uiso 1 1 d . . . . .
N1 N 0.6097(4) 0.8841(3) 0.6812(3) 0.0169(6) Uani 1 1 d . . . . .
N2 N 0.7850(4) 0.9478(3) 0.4643(3) 0.0171(6) Uani 1 1 d . . . . .
H2 H 0.767(6) 1.060(5) 0.475(4) 0.008(9) Uiso 1 1 d . . . . .
N3 N 0.5334(4) 0.6163(3) 0.7675(3) 0.0163(6) Uani 1 1 d . . . . .
N4 N 0.7176(4) 0.6892(3) 0.5477(3) 0.0148(6) Uani 1 1 d . . . . .
N5 N 0.9080(4) 0.7570(3) 0.3268(3) 0.0172(6) Uani 1 1 d . . . . .
N6 N 0.6345(4) 0.4284(3) 0.6329(3) 0.0171(6) Uani 1 1 d . . . . .
N7 N 0.8292(4) 0.4995(4) 0.4095(3) 0.0173(6) Uani 1 1 d . . . . .
C1 C 0.5323(5) 0.7672(4) 0.7855(4) 0.0159(7) Uani 1 1 d . . . . .
C2 C 0.7002(5) 0.8418(4) 0.5687(4) 0.0140(7) Uani 1 1 d . . . . .
C3 C 0.8895(5) 0.9085(4) 0.3433(4) 0.0153(7) Uani 1 1 d . . . . .
C4 C 0.6266(5) 0.5748(4) 0.6513(4) 0.0162(7) Uani 1 1 d . . . . .
C5 C 0.8200(5) 0.6475(4) 0.4254(4) 0.0138(7) Uani 1 1 d . . . . .
C6 C 0.7327(5) 0.3921(4) 0.5110(4) 0.0164(7) Uani 1 1 d . . . . .
Co2 Co 1.0000 0.5000 0.0000 0.0143(2) Uani 1 2 d S T P . .
O6 O 1.0031(4) 0.3520(3) 0.1978(3) 0.0180(5) Uani 1 1 d . . . . .
H6A H 0.968(8) 0.265(7) 0.217(6) 0.029(14) Uiso 1 1 d . . . . .
H6B H 0.947(8) 0.399(6) 0.256(6) 0.027(13) Uiso 1 1 d . . . . .
O7 O 1.0960(4) 0.6877(3) 0.0753(3) 0.0220(6) Uani 1 1 d . . . . .
H7A H 1.039(8) 0.709(7) 0.170(6) 0.042(15) Uiso 1 1 d . . . . .
H7B H 1.197(9) 0.730(6) 0.042(6) 0.036(14) Uiso 1 1 d . . . . .
O8 O 1.2799(4) 0.4186(3) -0.0665(3) 0.0199(6) Uani 1 1 d . . . . .
H8A H 1.345(8) 0.372(7) -0.015(6) 0.034(15) Uiso 1 1 d . . . . .
H8B H 1.361(8) 0.478(7) -0.123(6) 0.035(14) Uiso 1 1 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 O1 2.200(2) . ?
Co1 O1 2.200(2) 2_677 ?
Co1 O4 2.090(3) . ?
Co1 O4 2.090(3) 2_677 ?
Co1 O5 2.102(3) 2_677 ?
Co1 O5 2.102(3) . ?
O1 C1 1.258(4) . ?
O2 C3 1.236(4) . ?
O3 C6 1.254(4) . ?
O4 H4A 0.78(7) . ?
O4 H4B 0.77(6) . ?
O5 H5A 0.79(6) . ?
O5 H5B 0.89(6) . ?
N1 C1 1.383(4) . ?
N1 C2 1.298(4) . ?
N2 H2 0.99(4) . ?
N2 C2 1.345(4) . ?
N2 C3 1.394(4) . ?
N3 C1 1.357(4) . ?
N3 C4 1.333(5) . ?
N4 C2 1.375(4) . ?
N4 C4 1.401(4) . ?
N4 C5 1.407(4) . ?
N5 C3 1.352(5) . ?
N5 C5 1.341(4) . ?
N6 C4 1.316(5) . ?
N6 C6 1.375(5) . ?
N7 C5 1.321(5) . ?
N7 C6 1.371(5) . ?
Co2 O6 2.121(3) 2_765 ?
Co2 O6 2.122(3) . ?
Co2 O7 2.116(3) 2_765 ?
Co2 O7 2.116(3) . ?
Co2 O8 2.083(3) 2_765 ?
Co2 O8 2.083(3) . ?
O6 H6A 0.79(6) . ?
O6 H6B 0.80(6) . ?
O7 H7A 1.01(6) . ?
O7 H7B 0.82(6) . ?
O8 H8A 0.77(6) . ?
O8 H8B 0.87(6) . ?

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 O1 180.0 2_677 . ?
O4 Co1 O1 90.62(10) . . ?
O4 Co1 O1 90.62(10) 2_677 2_677 ?
O4 Co1 O1 89.38(10) 2_677 . ?
O4 Co1 O1 89.38(10) . 2_677 ?
O4 Co1 O4 180.00(16) 2_677 . ?
O4 Co1 O5 91.23(13) . . ?
O4 Co1 O5 88.77(13) 2_677 . ?
O4 Co1 O5 91.23(13) 2_677 2_677 ?
O4 Co1 O5 88.77(13) . 2_677 ?
O5 Co1 O1 89.83(10) 2_677 . ?
O5 Co1 O1 89.83(10) . 2_677 ?
O5 Co1 O1 90.17(10) . . ?
O5 Co1 O1 90.17(10) 2_677 2_677 ?
O5 Co1 O5 180.0 2_677 . ?
C1 O1 Co1 131.5(2) . . ?
Co1 O4 H4A 128(5) . . ?
Co1 O4 H4B 125(4) . . ?
H4A O4 H4B 104(6) . . ?
Co1 O5 H5A 142(4) . . ?
Co1 O5 H5B 106(4) . . ?
H5A O5 H5B 112(5) . . ?
C2 N1 C1 117.3(3) . . ?
C2 N2 H2 117(2) . . ?
C2 N2 C3 123.4(3) . . ?
C3 N2 H2 120(2) . . ?
C4 N3 C1 119.7(3) . . ?
C2 N4 C4 118.0(3) . . ?
C2 N4 C5 121.7(3) . . ?
C4 N4 C5 120.2(3) . . ?
C5 N5 C3 119.3(3) . . ?
C4 N6 C6 118.5(3) . . ?
C5 N7 C6 118.8(3) . . ?
O1 C1 N1 119.3(3) . . ?
O1 C1 N3 118.7(3) . . ?
N3 C1 N1 122.0(3) . . ?
N1 C2 N2 120.9(3) . . ?
N1 C2 N4 123.4(3) . . ?
N2 C2 N4 115.7(3) . . ?
O2 C3 N2 117.1(3) . . ?
O2 C3 N5 123.3(3) . . ?
N5 C3 N2 119.6(3) . . ?
N3 C4 N4 119.3(3) . . ?
N6 C4 N3 121.0(3) . . ?
N6 C4 N4 119.8(3) . . ?
N5 C5 N4 120.1(3) . . ?
N7 C5 N4 119.2(3) . . ?
N7 C5 N5 120.7(3) . . ?
O3 C6 N6 118.6(3) . . ?
O3 C6 N7 118.1(3) . . ?
N7 C6 N6 123.4(3) . . ?
O6 Co2 O6 180.0 2_765 . ?
O7 Co2 O6 90.94(11) . . ?
O7 Co2 O6 89.06(11) 2_765 . ?
O7 Co2 O6 90.94(11) 2_765 2_765 ?
O7 Co2 O6 89.06(11) . 2_765 ?
O7 Co2 O7 180.0 . 2_765 ?
O8 Co2 O6 91.24(11) 2_765 2_765 ?
O8 Co2 O6 91.24(11) . . ?
O8 Co2 O6 88.76(11) . 2_765 ?
O8 Co2 O6 88.76(11) 2_765 . ?
O8 Co2 O7 86.64(11) 2_765 . ?
O8 Co2 O7 93.36(11) 2_765 2_765 ?
O8 Co2 O7 93.36(11) . . ?
O8 Co2 O7 86.64(11) . 2_765 ?
O8 Co2 O8 180.0 2_765 . ?
Co2 O6 H6A 125(4) . . ?
Co2 O6 H6B 108(4) . . ?
H6A O6 H6B 107(5) . . ?
Co2 O7 H7A 120(3) . . ?
Co2 O7 H7B 123(4) . . ?
H7A O7 H7B 115(5) . . ?
Co2 O8 H8A 122(4) . . ?
Co2 O8 H8B 122(4) . . ?
H8A O8 H8B 102(5) . . ?

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
O4 H4B O2 0.77(6) 1.91(6) 2.678(4) 172(6) 1_456
O5 H5A N6 0.79(6) 2.00(6) 2.758(4) 162(6) 1_565
O5 H5B N1 0.89(6) 1.91(6) 2.747(4) 156(5) .
N2 H2 O3 0.99(4) 1.72(4) 2.714(4) 179(4) 1_565
O6 H6A O2 0.79(6) 2.12(6) 2.891(4) 163(5) 1_545
O6 H6B N7 0.80(6) 1.95(6) 2.745(4) 174(5) .
O7 H7A N5 1.01(6) 1.78(6) 2.785(4) 172(5) .
O7 H7B O1 0.82(6) 2.20(6) 2.991(4) 162(5) 1_654
O8 H8B N3 0.87(6) 1.85(6) 2.714(4) 175(5) 1_654

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
Co1 O1 C1 N1 -19.3(5) . . . . ?
Co1 O1 C1 N3 159.6(2) . . . . ?
C1 N1 C2 N2 -177.8(3) . . . . ?
C1 N1 C2 N4 1.7(5) . . . . ?
C1 N3 C4 N4 -1.7(5) . . . . ?
C1 N3 C4 N6 178.1(3) . . . . ?
C2 N1 C1 O1 172.6(3) . . . . ?
C2 N1 C1 N3 -6.2(5) . . . . ?
C2 N2 C3 O2 -178.4(3) . . . . ?
C2 N2 C3 N5 0.4(5) . . . . ?
C2 N4 C4 N3 -2.5(5) . . . . ?
C2 N4 C4 N6 177.7(3) . . . . ?
C2 N4 C5 N5 1.7(5) . . . . ?
C2 N4 C5 N7 -178.8(3) . . . . ?
C3 N2 C2 N1 177.8(3) . . . . ?
C3 N2 C2 N4 -1.8(5) . . . . ?
C3 N5 C5 N4 -3.2(5) . . . . ?
C3 N5 C5 N7 177.3(3) . . . . ?
C4 N3 C1 O1 -172.6(3) . . . . ?
C4 N3 C1 N1 6.3(5) . . . . ?
C4 N4 C2 N1 2.5(5) . . . . ?
C4 N4 C2 N2 -178.0(3) . . . . ?
C4 N4 C5 N5 -179.6(3) . . . . ?
C4 N4 C5 N7 -0.1(5) . . . . ?
C4 N6 C6 O3 -177.1(3) . . . . ?
C4 N6 C6 N7 2.5(5) . . . . ?
C5 N4 C2 N1 -178.8(3) . . . . ?
C5 N4 C2 N2 0.7(5) . . . . ?
C5 N4 C4 N3 178.8(3) . . . . ?
C5 N4 C4 N6 -1.1(5) . . . . ?
C5 N5 C3 O2 -179.2(3) . . . . ?
C5 N5 C3 N2 2.2(5) . . . . ?
C5 N7 C6 O3 176.0(3) . . . . ?
C5 N7 C6 N6 -3.6(5) . . . . ?
C6 N6 C4 N3 -180.0(3) . . . . ?
C6 N6 C4 N4 -0.1(5) . . . . ?
C6 N7 C5 N4 2.3(5) . . . . ?
C6 N7 C5 N5 -178.2(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ada117
_database_code_depnum_ccdc_archive 'CCDC 1867180'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;University of Montreal
Canada
;
_audit_update_record             
;
2018-09-11 deposited with the CCDC.	2019-04-15 downloaded from the CCDC.
;
_audit_creation_date             2018-09-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C12 H10 Mn0.31 N14 Ni0.69 O10, H12 Mn0.02 Ni0.98 O6'
_chemical_formula_sum            'C12 H22 Mn0.32 N14 Ni1.68 O16'
_chemical_formula_weight         734.65
_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 0.0140 0.0070 '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'
Mn Mn -0.0160 2.2330 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -1.3360 3.2900 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0390 0.0250 '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                   7.3080(16)
_cell_length_b                   8.6517(18)
_cell_length_c                   9.4153(18)
_cell_angle_alpha                78.474(15)
_cell_angle_beta                 83.477(14)
_cell_angle_gamma                87.509(15)
_cell_volume                     579.4(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4276
_cell_measurement_temperature    100
_cell_measurement_theta_max      61.129
_cell_measurement_theta_min      4.194
_shelx_estimated_absorpt_T_max   0.494
_shelx_estimated_absorpt_T_min   0.306
_exptl_absorpt_coefficient_mu    9.124
_exptl_absorpt_correction_T_max  0.3404
_exptl_absorpt_correction_T_min  0.1848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1448 before and 0.0782 after correction. The Ratio of minimum to maximum transmission is 0.5429. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.106
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Chunk
_exptl_crystal_F_000             375
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7945
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         61.932
_diffrn_reflns_theta_min         4.193
_diffrn_ambient_temperature      100
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1997
_reflns_number_total             2595
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.629
_refine_diff_density_min         -1.426
_refine_diff_density_rms         0.155
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2595
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1137
_refine_ls_R_factor_gt           0.0889
_refine_ls_restrained_S_all      1.060
_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)+(0.1105P)²+3.6237P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2235
_refine_ls_wR_factor_ref         0.2462
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Shared sites
{Mn1, Ni1}
{Mn2, Ni2}
3. Uiso/Uaniso restraints and constraints
Uanis(Mn1) = Uanis(Ni1)
Uanis(Mn2) = Uanis(Ni2)
4. Others
 Sof(Ni1)=0.5*(1-FVAR(2))
 Sof(Mn1)=0.5*FVAR(2)
 Sof(Ni2)=0.5*(1-FVAR(3))
 Sof(Mn2)=0.5*FVAR(3)
5.a Riding coordinates:
 O6(H6A,H6B)
5.b Rotating group:
 O4(H4A,H4B), O5(H5A,H5B), O7(H7A,H7B), O8(H8A,H8B)
5.c Aromatic/amide H refined with riding coordinates:
 N3(H3)
;
_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
Mn1 Mn 0.500000 1.000000 1.000000 0.0361(5) Uani 0.31(8) 2 d S T P . .
Ni1 Ni 0.500000 1.000000 1.000000 0.0361(5) Uani 0.69(8) 2 d S T P . .
N1 N 0.6097(8) 0.8787(7) 0.6847(7) 0.0406(14) Uani 1 1 d . . . . .
C1 C 0.5277(10) 0.7623(8) 0.7898(8) 0.0378(15) Uani 1 1 d . . . . .
O1 O 0.4487(7) 0.8007(5) 0.9049(6) 0.0408(12) Uani 1 1 d . . . . .
C2 C 0.6994(9) 0.8362(8) 0.5713(8) 0.0347(15) Uani 1 1 d . . . . .
O2 O 0.9577(8) 1.0115(6) 0.2487(6) 0.0508(14) Uani 1 1 d . . . . .
N2 N 0.5285(9) 0.6098(7) 0.7748(7) 0.0411(14) Uani 1 1 d . . . . .
N3 N 0.7873(9) 0.9422(7) 0.4635(7) 0.0406(14) Uani 1 1 d . . . . .
H3 H 0.780256 1.042161 0.470933 0.049 Uiso 1 1 calc R . . . .
C3 C 0.6212(10) 0.5680(8) 0.6589(8) 0.0359(15) Uani 1 1 d . . . . .
O3 O 0.7242(7) 0.2465(5) 0.4966(5) 0.0436(13) Uani 1 1 d . . . . .
N4 N 0.7141(8) 0.6833(7) 0.5514(6) 0.0374(13) Uani 1 1 d . . . . .
C4 C 0.8875(10) 0.9030(8) 0.3421(8) 0.0390(16) Uani 1 1 d . . . . .
O4 O 0.2157(7) 1.0605(6) 1.0165(6) 0.0417(12) Uani 1 1 d . . . . .
H4A H 0.165832 1.033054 1.105497 0.063 Uiso 1 1 d GR . . . .
H4B H 0.159122 1.012619 0.962070 0.063 Uiso 1 1 d GR . . . .
N5 N 0.6282(8) 0.4210(7) 0.6403(7) 0.0392(14) Uani 1 1 d . . . . .
O5 O 0.4924(8) 0.8582(6) 1.2048(6) 0.0476(14) Uani 1 1 d . . . . .
H5A H 0.421852 0.777267 1.211440 0.071 Uiso 1 1 d GR . . . .
H5B H 0.448375 0.910803 1.271809 0.071 Uiso 1 1 d GR . . . .
C5 C 0.8192(9) 0.6411(8) 0.4282(7) 0.0351(15) Uani 1 1 d . . . . .
C6 C 0.7246(10) 0.3848(8) 0.5168(8) 0.0382(15) Uani 1 1 d . . . . .
N6 N 0.9105(8) 0.7507(7) 0.3287(7) 0.0403(14) Uani 1 1 d . . . . .
N7 N 0.8268(9) 0.4937(7) 0.4129(7) 0.0402(14) Uani 1 1 d . . . . .
Mn2 Mn 1.000000 0.500000 0.000000 0.0354(5) Uani 0.02(8) 2 d S T P . .
Ni2 Ni 1.000000 0.500000 0.000000 0.0354(5) Uani 0.98(8) 2 d S T P . .
O6 O 0.7424(7) 0.5840(6) 0.0640(6) 0.0467(13) Uani 1 1 d . . . . .
H6A H 0.747166 0.672045 0.088818 0.070 Uiso 1 1 d R . . . .
H6B H 0.688296 0.516834 0.135578 0.070 Uiso 1 1 d R . . . .
O7 O 0.8923(8) 0.3179(6) -0.0742(6) 0.0434(13) Uani 1 1 d . . . . .
H7A H 0.950172 0.306469 -0.158625 0.065 Uiso 1 1 d GR . . . .
H7B H 0.774524 0.334664 -0.086232 0.065 Uiso 1 1 d GR . . . .
O8 O 1.0061(7) 0.3523(5) 0.2015(5) 0.0375(11) Uani 1 1 d . . . . .
H8A H 0.960544 0.259961 0.202435 0.056 Uiso 1 1 d GR . . . .
H8B H 0.941751 0.392863 0.269992 0.056 Uiso 1 1 d GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O1 2.160(4) . ?
Mn1 O1 2.160(4) 2_677 ?
Mn1 O4 2.117(5) 2_677 ?
Mn1 O4 2.117(5) . ?
Mn1 O5 2.064(5) . ?
Mn1 O5 2.064(5) 2_677 ?
N1 C1 1.368(9) . ?
N1 C2 1.297(8) . ?
C1 O1 1.266(8) . ?
C1 N2 1.354(9) . ?
C2 N3 1.348(9) . ?
C2 N4 1.371(8) . ?
O2 C4 1.236(9) . ?
N2 C3 1.323(9) . ?
N3 H3 0.8800 . ?
N3 C4 1.379(9) . ?
C3 N4 1.407(9) . ?
C3 N5 1.316(8) . ?
O3 C6 1.249(8) . ?
N4 C5 1.418(8) . ?
C4 N6 1.350(9) . ?
O4 H4A 0.8657 . ?
O4 H4B 0.8676 . ?
N5 C6 1.373(9) . ?
O5 H5A 0.8760 . ?
O5 H5B 0.8743 . ?
C5 N6 1.334(9) . ?
C5 N7 1.310(9) . ?
C6 N7 1.389(9) . ?
Mn2 O6 2.058(5) 2_765 ?
Mn2 O6 2.058(5) . ?
Mn2 O7 2.064(4) . ?
Mn2 O7 2.064(5) 2_765 ?
Mn2 O8 2.069(5) . ?
Mn2 O8 2.069(5) 2_765 ?
O6 H6A 0.8436 . ?
O6 H6B 0.8667 . ?
O7 H7A 0.8787 . ?
O7 H7B 0.8833 . ?
O8 H8A 0.8769 . ?
O8 H8B 0.8758 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Mn1 O1 180.0(3) 2_677 . ?
O4 Mn1 O1 89.27(19) 2_677 . ?
O4 Mn1 O1 90.72(19) . . ?
O4 Mn1 O1 89.27(19) . 2_677 ?
O4 Mn1 O1 90.73(19) 2_677 2_677 ?
O4 Mn1 O4 180.0 2_677 . ?
O5 Mn1 O1 91.1(2) . . ?
O5 Mn1 O1 91.1(2) 2_677 2_677 ?
O5 Mn1 O1 88.9(2) 2_677 . ?
O5 Mn1 O1 88.9(2) . 2_677 ?
O5 Mn1 O4 95.4(2) . . ?
O5 Mn1 O4 84.6(2) 2_677 . ?
O5 Mn1 O4 95.4(2) 2_677 2_677 ?
O5 Mn1 O4 84.6(2) . 2_677 ?
O5 Mn1 O5 180.0 2_677 . ?
C2 N1 C1 117.1(6) . . ?
O1 C1 N1 117.8(6) . . ?
O1 C1 N2 119.6(6) . . ?
N2 C1 N1 122.6(6) . . ?
C1 O1 Mn1 128.7(4) . . ?
N1 C2 N3 121.3(6) . . ?
N1 C2 N4 123.7(6) . . ?
N3 C2 N4 114.9(6) . . ?
C3 N2 C1 119.5(6) . . ?
C2 N3 H3 118.2 . . ?
C2 N3 C4 123.7(6) . . ?
C4 N3 H3 118.2 . . ?
N2 C3 N4 119.5(6) . . ?
N5 C3 N2 121.8(6) . . ?
N5 C3 N4 118.7(6) . . ?
C2 N4 C3 117.4(6) . . ?
C2 N4 C5 121.9(6) . . ?
C3 N4 C5 120.7(6) . . ?
O2 C4 N3 117.6(6) . . ?
O2 C4 N6 121.8(6) . . ?
N6 C4 N3 120.6(6) . . ?
Mn1 O4 H4A 110.9 . . ?
Mn1 O4 H4B 110.3 . . ?
H4A O4 H4B 108.1 . . ?
C3 N5 C6 119.3(6) . . ?
Mn1 O5 H5A 110.7 . . ?
Mn1 O5 H5B 110.7 . . ?
H5A O5 H5B 107.9 . . ?
N6 C5 N4 120.3(6) . . ?
N7 C5 N4 119.6(6) . . ?
N7 C5 N6 120.1(6) . . ?
O3 C6 N5 119.1(6) . . ?
O3 C6 N7 117.4(6) . . ?
N5 C6 N7 123.5(6) . . ?
C5 N6 C4 118.3(6) . . ?
C5 N7 C6 118.0(6) . . ?
O6 Mn2 O6 180.0 2_765 . ?
O6 Mn2 O7 87.6(2) 2_765 . ?
O6 Mn2 O7 87.6(2) . 2_765 ?
O6 Mn2 O7 92.4(2) . . ?
O6 Mn2 O7 92.4(2) 2_765 2_765 ?
O6 Mn2 O8 90.6(2) . . ?
O6 Mn2 O8 89.4(2) 2_765 . ?
O6 Mn2 O8 89.4(2) . 2_765 ?
O6 Mn2 O8 90.6(2) 2_765 2_765 ?
O7 Mn2 O7 180.0 . 2_765 ?
O7 Mn2 O8 88.63(19) 2_765 2_765 ?
O7 Mn2 O8 91.37(19) . 2_765 ?
O7 Mn2 O8 91.37(19) 2_765 . ?
O7 Mn2 O8 88.63(19) . . ?
O8 Mn2 O8 180.0(3) . 2_765 ?
Mn2 O6 H6A 111.8 . . ?
Mn2 O6 H6B 110.3 . . ?
H6A O6 H6B 109.6 . . ?
Mn2 O7 H7A 111.1 . . ?
Mn2 O7 H7B 111.8 . . ?
H7A O7 H7B 107.2 . . ?
Mn2 O8 H8A 111.4 . . ?
Mn2 O8 H8B 111.0 . . ?
H8A O8 H8B 107.7 . . ?

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
_geom_hbond_publ_flag
N3 H3 O3 0.88 1.85 2.725(7) 170.4 1_565 yes
O4 H4A O2 0.87 1.90 2.698(7) 151.7 1_456 yes
O4 H4B O2 0.87 2.30 3.105(8) 154.9 2_676 yes
O5 H5A N5 0.88 2.00 2.688(8) 134.4 2_667 yes
O5 H5B N1 0.87 1.96 2.728(7) 145.2 2_677 yes
O5 H5B O3 0.87 2.56 3.055(7) 117.0 2_667 yes
O6 H6A O4 0.84 2.34 3.038(7) 140.0 2_676 yes
O6 H6B N2 0.87 1.98 2.761(8) 150.2 2_666 yes
O7 H7A N6 0.88 1.94 2.807(8) 171.0 2_765 yes
O7 H7B O1 0.88 2.38 2.911(7) 118.5 2_666 yes
O8 H8A O2 0.88 2.11 2.923(7) 154.7 1_545 yes
O8 H8B O3 0.88 2.65 3.263(7) 128.3 . yes
O8 H8B N7 0.88 1.85 2.723(7) 173.7 . yes

_olex2_submission_special_instructions 'No special instructions were received'
