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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1818907'
_audit_update_record             
;
2018-01-23 deposited with the CCDC.
2018-10-02 downloaded from the CCDC.
;
_audit_creation_date             2017-07-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C6 O12 Zn2, 2(C6 H8 N3 O)'
_chemical_formula_sum            'C18 H16 N6 O14 Zn2'
_chemical_formula_weight         671.11
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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                   8.4179(3)
_cell_length_b                   9.1478(4)
_cell_length_c                   16.4206(5)
_cell_angle_alpha                84.686(3)
_cell_angle_beta                 84.283(3)
_cell_angle_gamma                71.497(3)
_cell_volume                     1190.64(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6908
_cell_measurement_temperature    292.3(6)
_cell_measurement_theta_max      28.7890
_cell_measurement_theta_min      3.9410
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.872
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14200
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.441
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.3(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -21.00   89.00   1.0000   10.5950
omega____ theta____ kappa____ phi______ frames
    -       16.8469   19.0000   60.0000 110

#__ type_ start__ end____ width___ exp.time_
  2 omega  -52.00   35.00   1.0000   10.5950
omega____ theta____ kappa____ phi______ frames
    -       16.8469  -57.0000 -120.0000 87

#__ type_ start__ end____ width___ exp.time_
  3 omega  -12.00   86.00   1.0000   10.5950
omega____ theta____ kappa____ phi______ frames
    -       16.8469   77.0000  -60.0000 98

#__ type_ start__ end____ width___ exp.time_
  4 omega   35.00   91.00   1.0000   10.5950
omega____ theta____ kappa____ phi______ frames
    -       16.8469  178.0000  -90.0000 56

#__ type_ start__ end____ width___ exp.time_
  5 omega  -12.00   86.00   1.0000   10.5950
omega____ theta____ kappa____ phi______ frames
    -       16.8469   77.0000   60.0000 98

#__ type_ start__ end____ width___ exp.time_
  6 omega  -55.00   55.00   1.0000   10.5950
omega____ theta____ kappa____ phi______ frames
    -       16.8469  -19.0000   60.0000 110

#__ type_ start__ end____ width___ exp.time_
  7 omega  -63.00   -9.00   1.0000   10.5950
omega____ theta____ kappa____ phi______ frames
    -      -17.7844  107.0000  120.0000 54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0084022000
_diffrn_orient_matrix_UB_12      -0.0779877000
_diffrn_orient_matrix_UB_13      0.0131573000
_diffrn_orient_matrix_UB_21      -0.0314599000
_diffrn_orient_matrix_UB_22      0.0226491000
_diffrn_orient_matrix_UB_23      0.0401359000
_diffrn_orient_matrix_UB_31      -0.0829375000
_diffrn_orient_matrix_UB_32      0.0108845000
_diffrn_orient_matrix_UB_33      -0.0104155000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4118
_reflns_number_total             4854
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.768
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4854
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0320
_refine_ls_restrained_S_all      1.120
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0270P)²+1.1221P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0844
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C13(H13), C14(H14), N1(H1), N2(H2), N3(H3), N4(H4), N5(H5),
 N6(H6)
;
_atom_sites_solution_hydrogens   geom
_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 0.51954(4) 0.48763(4) 0.33647(2) 0.03056(10) Uani 1 1 d . . . . .
Zn2 Zn 0.49215(4) 1.02375(4) 0.15973(2) 0.03456(10) Uani 1 1 d . . . . .
O1 O 0.6474(2) 0.2587(2) 0.31712(12) 0.0355(5) Uani 1 1 d . . . . .
O2 O 0.6532(2) 0.0758(2) 0.23536(12) 0.0379(5) Uani 1 1 d . . . . .
O3 O 0.3675(2) 0.4451(2) 0.25196(12) 0.0349(4) Uani 1 1 d . . . . .
O4 O 0.3654(2) 0.2583(2) 0.17491(12) 0.0366(5) Uani 1 1 d . . . . .
O5 O 0.6581(2) 0.5731(2) 0.24357(12) 0.0367(5) Uani 1 1 d . . . . .
O6 O 0.6403(3) 0.7881(2) 0.16464(12) 0.0396(5) Uani 1 1 d . . . . .
O7 O 0.3719(2) 0.7220(2) 0.32977(12) 0.0388(5) Uani 1 1 d . . . . .
O8 O 0.3633(3) 0.9402(2) 0.25682(12) 0.0406(5) Uani 1 1 d . . . . .
O9 O 0.6610(2) 0.5115(3) 0.42695(12) 0.0396(5) Uani 1 1 d . . . . .
O10 O 0.6361(2) 0.5433(2) 0.56033(11) 0.0362(5) Uani 1 1 d . . . . .
O11 O 0.3380(3) 1.0004(3) 0.07551(13) 0.0439(5) Uani 1 1 d . . . . .
O12 O 0.3638(2) 0.9426(2) -0.05451(12) 0.0360(4) Uani 1 1 d . . . . .
O13 O -0.0994(3) 0.3248(3) 0.12171(14) 0.0553(6) Uani 1 1 d . . . . .
O14 O 1.0643(3) 1.1970(3) 0.59311(15) 0.0571(6) Uani 1 1 d . . . . .
C1 C 0.5911(3) 0.2057(3) 0.26336(16) 0.0284(6) Uani 1 1 d . . . . .
C2 C 0.4263(3) 0.3117(3) 0.22706(15) 0.0274(5) Uani 1 1 d . . . . .
C3 C 0.5912(3) 0.7130(3) 0.22244(16) 0.0292(6) Uani 1 1 d . . . . .
C4 C 0.4273(3) 0.7998(3) 0.27417(16) 0.0311(6) Uani 1 1 d . . . . .
C5 C 0.5861(3) 0.5157(3) 0.49570(16) 0.0279(6) Uani 1 1 d . . . . .
C6 C 0.4133(3) 0.9835(3) 0.00615(17) 0.0308(6) Uani 1 1 d . . . . .
C7 C 0.0317(4) 0.8120(4) 0.2030(2) 0.0463(8) Uani 1 1 d . . . . .
H7 H 0.0109 0.8287 0.2586 0.056 Uiso 1 1 calc R . . . .
C8 C 0.0143(4) 0.8375(4) 0.0709(2) 0.0434(7) Uani 1 1 d . . . . .
H8 H -0.0240 0.8768 0.0196 0.052 Uiso 1 1 calc R . . . .
C9 C 0.1430(3) 0.7096(3) 0.08624(17) 0.0325(6) Uani 1 1 d . . . . .
C10 C 0.2617(4) 0.5973(4) 0.03066(19) 0.0406(7) Uani 1 1 d . . . . .
H10A H 0.3534 0.5313 0.0614 0.049 Uiso 1 1 calc R . . . .
H10B H 0.3087 0.6536 -0.0130 0.049 Uiso 1 1 calc R . . . .
C11 C 0.1773(4) 0.4959(4) -0.00734(18) 0.0410(7) Uani 1 1 d . . . . .
H11 H 0.2651 0.4211 -0.0395 0.049 Uiso 1 1 calc R . . . .
C12 C -0.0516(4) 0.4043(4) 0.06669(18) 0.0418(7) Uani 1 1 d . . . . .
C13 C 1.0101(4) 0.5406(4) 0.65988(19) 0.0388(7) Uani 1 1 d . . . . .
H13 H 1.0592 0.4340 0.6652 0.047 Uiso 1 1 calc R . . . .
C14 C 0.9377(4) 0.7864(4) 0.68071(19) 0.0412(7) Uani 1 1 d . . . . .
H14 H 0.9306 0.8772 0.7041 0.049 Uiso 1 1 calc R . . . .
C15 C 0.8581(3) 0.7747(3) 0.61545(17) 0.0318(6) Uani 1 1 d . . . . .
C16 C 0.7418(3) 0.8917(4) 0.56144(18) 0.0384(7) Uani 1 1 d . . . . .
H16A H 0.6523 0.9584 0.5956 0.046 Uiso 1 1 calc R . . . .
H16B H 0.6910 0.8387 0.5283 0.046 Uiso 1 1 calc R . . . .
C17 C 0.8268(4) 0.9924(3) 0.50434(18) 0.0363(6) Uani 1 1 d . . . . .
H17 H 0.7419 1.0589 0.4689 0.044 Uiso 1 1 calc R . . . .
C18 C 1.0331(4) 1.1077(3) 0.55089(18) 0.0392(7) Uani 1 1 d . . . . .
N1 N -0.0501(3) 0.8993(3) 0.14403(19) 0.0489(7) Uani 1 1 d . . . . .
H1 H -0.1322 0.9831 0.1502 0.059 Uiso 1 1 calc R . . . .
N2 N 0.1499(3) 0.6949(3) 0.16987(15) 0.0383(6) Uani 1 1 d . . . . .
H2 H 0.2200 0.6213 0.1966 0.046 Uiso 1 1 calc R . . . .
N3 N 0.1050(3) 0.4088(3) 0.05595(16) 0.0446(6) Uani 1 1 d . . . . .
H3 H 0.1724 0.3531 0.0909 0.054 Uiso 1 1 calc R . . . .
N4 N 1.0305(3) 0.6406(3) 0.70628(15) 0.0399(6) Uani 1 1 d . . . . .
H4 H 1.0930 0.6180 0.7469 0.048 Uiso 1 1 calc R . . . .
N5 N 0.9066(3) 0.6184(3) 0.60386(15) 0.0370(6) Uani 1 1 d . . . . .
H5 H 0.8745 0.5778 0.5659 0.044 Uiso 1 1 calc R . . . .
N6 N 0.8808(3) 1.0929(3) 0.55165(15) 0.0402(6) Uani 1 1 d . . . . .
H6 H 0.8046 1.1499 0.5842 0.048 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 2.0662(19) . ?
Zn1 O3 2.1176(19) . ?
Zn1 O5 2.0740(19) . ?
Zn1 O7 2.1085(19) . ?
Zn1 O9 2.0618(19) . ?
Zn1 O10 2.0910(19) 2_666 ?
Zn2 O2 2.112(2) 1_565 ?
Zn2 O4 2.0971(19) 1_565 ?
Zn2 O6 2.119(2) . ?
Zn2 O8 2.064(2) . ?
Zn2 O11 2.057(2) . ?
Zn2 O12 2.067(2) 2_675 ?
O1 C1 1.244(3) . ?
O2 Zn2 2.112(2) 1_545 ?
O2 C1 1.248(3) . ?
O3 C2 1.253(3) . ?
O4 Zn2 2.0971(19) 1_545 ?
O4 C2 1.248(3) . ?
O5 C3 1.255(3) . ?
O6 C3 1.236(3) . ?
O7 C4 1.250(3) . ?
O8 C4 1.243(3) . ?
O9 C5 1.235(3) . ?
O10 Zn1 2.0910(19) 2_666 ?
O10 C5 1.254(3) . ?
O11 C6 1.245(3) . ?
O12 Zn2 2.067(2) 2_675 ?
O12 C6 1.248(3) . ?
O13 C12 1.224(4) . ?
O14 C18 1.222(4) . ?
C1 C2 1.557(4) . ?
C3 C4 1.565(4) . ?
C5 C5 1.554(5) 2_666 ?
C6 C6 1.571(5) 2_675 ?
C7 H7 0.9300 . ?
C7 N1 1.300(4) . ?
C7 N2 1.325(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.342(4) . ?
C8 N1 1.363(4) . ?
C9 C10 1.492(4) . ?
C9 N2 1.373(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.539(4) . ?
C11 H11 0.9800 . ?
C11 C12 1.526(4) 2_565 ?
C11 N3 1.454(4) . ?
C12 C11 1.526(4) 2_565 ?
C12 N3 1.325(4) . ?
C13 H13 0.9300 . ?
C13 N4 1.304(4) . ?
C13 N5 1.325(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.348(4) . ?
C14 N4 1.366(4) . ?
C15 C16 1.491(4) . ?
C15 N5 1.382(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.537(4) . ?
C17 H17 0.9800 . ?
C17 C18 1.519(4) 2_776 ?
C17 N6 1.458(4) . ?
C18 C17 1.519(4) 2_776 ?
C18 N6 1.330(4) . ?
N1 H1 0.8600 . ?
N2 H2 0.8600 . ?
N3 H3 0.8600 . ?
N4 H4 0.8600 . ?
N5 H5 0.8600 . ?
N6 H6 0.8600 . ?

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 O3 79.88(7) . . ?
O1 Zn1 O5 94.46(8) . . ?
O1 Zn1 O7 167.20(8) . . ?
O1 Zn1 O10 99.04(8) . 2_666 ?
O5 Zn1 O3 91.99(8) . . ?
O5 Zn1 O7 80.19(7) . . ?
O5 Zn1 O10 165.85(8) . 2_666 ?
O7 Zn1 O3 88.64(8) . . ?
O9 Zn1 O1 97.25(8) . . ?
O9 Zn1 O3 173.98(8) . . ?
O9 Zn1 O5 93.52(8) . . ?
O9 Zn1 O7 94.69(9) . . ?
O9 Zn1 O10 80.65(7) . 2_666 ?
O10 Zn1 O3 94.51(7) 2_666 . ?
O10 Zn1 O7 87.41(8) 2_666 . ?
O2 Zn2 O6 90.67(8) 1_565 . ?
O4 Zn2 O2 79.51(7) 1_565 1_565 ?
O4 Zn2 O6 169.40(8) 1_565 . ?
O8 Zn2 O2 93.73(9) . 1_565 ?
O8 Zn2 O4 96.14(8) . 1_565 ?
O8 Zn2 O6 80.42(7) . . ?
O8 Zn2 O12 167.16(8) . 2_675 ?
O11 Zn2 O2 171.75(9) . 1_565 ?
O11 Zn2 O4 95.26(8) . 1_565 ?
O11 Zn2 O6 94.94(9) . . ?
O11 Zn2 O8 93.18(9) . . ?
O11 Zn2 O12 81.99(8) . 2_675 ?
O12 Zn2 O2 92.16(8) 2_675 1_565 ?
O12 Zn2 O4 96.15(8) 2_675 1_565 ?
O12 Zn2 O6 88.12(8) 2_675 . ?
C1 O1 Zn1 113.91(16) . . ?
C1 O2 Zn2 112.68(16) . 1_545 ?
C2 O3 Zn1 112.11(16) . . ?
C2 O4 Zn2 112.50(16) . 1_545 ?
C3 O5 Zn1 113.70(16) . . ?
C3 O6 Zn2 111.84(16) . . ?
C4 O7 Zn1 112.35(16) . . ?
C4 O8 Zn2 113.11(17) . . ?
C5 O9 Zn1 112.47(16) . . ?
C5 O10 Zn1 111.85(16) . 2_666 ?
C6 O11 Zn2 110.74(17) . . ?
C6 O12 Zn2 110.39(17) . 2_675 ?
O1 C1 O2 126.7(2) . . ?
O1 C1 C2 117.0(2) . . ?
O2 C1 C2 116.3(2) . . ?
O3 C2 C1 116.8(2) . . ?
O4 C2 O3 125.5(2) . . ?
O4 C2 C1 117.7(2) . . ?
O5 C3 C4 116.3(2) . . ?
O6 C3 O5 126.7(2) . . ?
O6 C3 C4 117.0(2) . . ?
O7 C4 C3 117.2(2) . . ?
O8 C4 O7 125.4(2) . . ?
O8 C4 C3 117.5(2) . . ?
O9 C5 O10 125.8(2) . . ?
O9 C5 C5 118.0(3) . 2_666 ?
O10 C5 C5 116.2(3) . 2_666 ?
O11 C6 O12 125.9(3) . . ?
O11 C6 C6 117.1(3) . 2_675 ?
O12 C6 C6 117.0(3) . 2_675 ?
N1 C7 H7 126.0 . . ?
N1 C7 N2 107.9(3) . . ?
N2 C7 H7 126.0 . . ?
C9 C8 H8 126.3 . . ?
C9 C8 N1 107.5(3) . . ?
N1 C8 H8 126.3 . . ?
C8 C9 C10 131.6(3) . . ?
C8 C9 N2 105.6(3) . . ?
N2 C9 C10 122.7(2) . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C9 C10 C11 112.8(2) . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C10 C11 H11 107.4 . . ?
C12 C11 C10 109.5(3) 2_565 . ?
C12 C11 H11 107.4 2_565 . ?
N3 C11 C10 111.0(2) . . ?
N3 C11 H11 107.4 . . ?
N3 C11 C12 113.8(3) . 2_565 ?
O13 C12 C11 119.0(3) . 2_565 ?
O13 C12 N3 123.2(3) . . ?
N3 C12 C11 117.8(3) . 2_565 ?
N4 C13 H13 126.2 . . ?
N4 C13 N5 107.6(3) . . ?
N5 C13 H13 126.2 . . ?
C15 C14 H14 126.2 . . ?
C15 C14 N4 107.6(3) . . ?
N4 C14 H14 126.2 . . ?
C14 C15 C16 132.7(3) . . ?
C14 C15 N5 105.1(3) . . ?
N5 C15 C16 122.2(2) . . ?
C15 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
C15 C16 C17 114.0(2) . . ?
H16A C16 H16B 107.6 . . ?
C17 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C16 C17 H17 107.3 . . ?
C18 C17 C16 110.4(2) 2_776 . ?
C18 C17 H17 107.3 2_776 . ?
N6 C17 C16 110.5(2) . . ?
N6 C17 H17 107.3 . . ?
N6 C17 C18 113.7(2) . 2_776 ?
O14 C18 C17 119.2(3) . 2_776 ?
O14 C18 N6 122.7(3) . . ?
N6 C18 C17 118.1(3) . 2_776 ?
C7 N1 C8 109.5(3) . . ?
C7 N1 H1 125.2 . . ?
C8 N1 H1 125.2 . . ?
C7 N2 C9 109.4(3) . . ?
C7 N2 H2 125.3 . . ?
C9 N2 H2 125.3 . . ?
C11 N3 H3 115.8 . . ?
C12 N3 C11 128.4(3) . . ?
C12 N3 H3 115.8 . . ?
C13 N4 C14 109.8(3) . . ?
C13 N4 H4 125.1 . . ?
C14 N4 H4 125.1 . . ?
C13 N5 C15 109.9(2) . . ?
C13 N5 H5 125.1 . . ?
C15 N5 H5 125.1 . . ?
C17 N6 H6 115.9 . . ?
C18 N6 C17 128.2(2) . . ?
C18 N6 H6 115.9 . . ?

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
N1 H1 O2 0.86 2.16 2.870(3) 139.2 1_465
N2 H2 O3 0.86 1.91 2.768(3) 174.8 .
N3 H3 O4 0.86 2.15 2.993(3) 166.4 .
N4 H4 O5 0.86 2.27 2.872(3) 127.0 2_766
N4 H4 O13 0.86 2.28 3.004(3) 142.4 2_666
N5 H5 O10 0.86 2.14 2.753(3) 127.9 .
N6 H6 O7 0.86 2.09 2.947(3) 175.8 2_676

_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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1818908'
_audit_update_record             
;
2018-01-23 deposited with the CCDC.
2018-10-02 downloaded from the CCDC.
;
_audit_creation_date             2016-10-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H14 Mn N6 O6'
_chemical_formula_sum            'C14 H14 Mn N6 O6'
_chemical_formula_weight         417.25
_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 0.0181 0.0091 '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 -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.78208(16)
_cell_length_b                   11.57400(17)
_cell_length_c                   14.9180(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.6582(14)
_cell_angle_gamma                90
_cell_volume                     1680.76(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4765
_cell_measurement_temperature    293(1)
_cell_measurement_theta_max      72.3370
_cell_measurement_theta_min      4.5230
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.837
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.649
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8453
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         4.542
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   20.00  104.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000    0.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega   20.00  104.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000  120.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega  -31.00   53.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -57.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega   10.00  104.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000 -120.0000 94

#__ type_ start__ end____ width___ exp.time_
  5 omega    1.00   27.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   93.0000  -47.6852 26

#__ type_ start__ end____ width___ exp.time_
  6 omega  -31.00   53.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -57.0000 -120.0000 84

#__ type_ start__ end____ width___ exp.time_
  7 omega   23.00   90.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171 -125.0000 -150.0000 67

#__ type_ start__ end____ width___ exp.time_
  8 omega   38.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

#__ type_ start__ end____ width___ exp.time_
  9 omega  100.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 78

#__ type_ start__ end____ width___ exp.time_
 10 omega   87.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   90.0000 91

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00  113.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -107.0000   92.0000 75

#__ type_ start__ end____ width___ exp.time_
 12 omega   39.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

#__ type_ start__ end____ width___ exp.time_
 13 omega   38.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
 14 omega   38.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
 15 omega   40.00   98.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 58

#__ type_ start__ end____ width___ exp.time_
 16 omega   41.00  126.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   60.0000 85

#__ type_ start__ end____ width___ exp.time_
 17 omega  -31.00   14.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -57.0000   90.0000 45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0223878000
_diffrn_orient_matrix_UB_12      -0.0804556000
_diffrn_orient_matrix_UB_13      -0.0794878000
_diffrn_orient_matrix_UB_21      -0.0090917000
_diffrn_orient_matrix_UB_22      -0.1058868000
_diffrn_orient_matrix_UB_23      0.0616838000
_diffrn_orient_matrix_UB_31      -0.1564420000
_diffrn_orient_matrix_UB_32      -0.0053622000
_diffrn_orient_matrix_UB_33      -0.0253759000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2777
_reflns_number_total             3002
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3002
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      0.982
_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)+(0.0892P)²+0.4863P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1211
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C13(H13), C14(H14), N2(H2), N3(H3A), N4(H4A), N5(H5)
;
_atom_sites_solution_hydrogens   geom
_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 0.25254(3) 0.37220(3) 0.49422(2) 0.02401(16) Uani 1 1 d . . . . .
O1 O 0.06412(17) 0.38215(14) 0.56402(12) 0.0312(4) Uani 1 1 d . . . . .
O2 O -0.14458(17) 0.46184(15) 0.55089(13) 0.0372(4) Uani 1 1 d . . . . .
O3 O 0.39682(16) 0.46955(15) 0.58626(10) 0.0296(4) Uani 1 1 d . . . . .
O4 O 0.58904(17) 0.57289(16) 0.59011(11) 0.0337(4) Uani 1 1 d . . . . .
O5 O 0.8233(3) 0.1059(2) 0.56935(15) 0.0592(6) Uani 1 1 d . . . . .
O6 O 0.6585(2) 0.29453(18) 0.86768(15) 0.0522(5) Uani 1 1 d . . . . .
C1 C -0.0242(2) 0.45482(19) 0.53357(15) 0.0261(5) Uani 1 1 d . . . . .
C2 C 0.4963(2) 0.51239(19) 0.55122(14) 0.0242(5) Uani 1 1 d . . . . .
C3 C 0.2727(3) 0.1058(2) 0.5492(2) 0.0423(6) Uani 1 1 d . . . . .
H3 H 0.1859 0.0902 0.5206 0.051 Uiso 1 1 calc R . . . .
C4 C 0.4523(3) 0.1922(2) 0.6060(2) 0.0483(8) Uani 1 1 d . . . . .
H4 H 0.5139 0.2509 0.6241 0.058 Uiso 1 1 calc R . . . .
C5 C 0.4769(3) 0.0778(2) 0.62019(17) 0.0336(5) Uani 1 1 d . . . . .
C6 C 0.5951(3) 0.0072(2) 0.66147(19) 0.0372(6) Uani 1 1 d . . . . .
H6A H 0.6259 -0.0426 0.6153 0.045 Uiso 1 1 calc R . . . .
H6B H 0.5621 -0.0421 0.7073 0.045 Uiso 1 1 calc R . . . .
C7 C 0.7186(3) 0.0754(2) 0.70411(17) 0.0322(5) Uani 1 1 d . . . . .
H7 H 0.7892 0.0189 0.7251 0.039 Uiso 1 1 calc R . . . .
C8 C 0.7794(3) 0.1511(2) 0.63468(18) 0.0366(6) Uani 1 1 d . . . . .
C9 C 0.6918(3) 0.2514(2) 0.79774(18) 0.0337(5) Uani 1 1 d . . . . .
C10 C 0.7440(3) 0.3279(2) 0.72633(17) 0.0322(5) Uani 1 1 d . . . . .
H10 H 0.6701 0.3817 0.7057 0.039 Uiso 1 1 calc R . . . .
C11 C 0.8679(3) 0.4002(2) 0.76664(18) 0.0333(5) Uani 1 1 d . . . . .
H11A H 0.8947 0.4532 0.7211 0.040 Uiso 1 1 calc R . . . .
H11B H 0.8403 0.4458 0.8164 0.040 Uiso 1 1 calc R . . . .
C12 C 0.9881(2) 0.3278(2) 0.79931(16) 0.0303(5) Uani 1 1 d . . . . .
C13 C 1.0255(3) 0.2813(2) 0.88152(17) 0.0346(5) Uani 1 1 d . . . . .
H13 H 0.9780 0.2904 0.9321 0.042 Uiso 1 1 calc R . . . .
C14 C 1.1776(3) 0.2271(2) 0.79565(17) 0.0370(6) Uani 1 1 d . . . . .
H14 H 1.2543 0.1930 0.7745 0.044 Uiso 1 1 calc R . . . .
N1 N 0.3243(2) 0.20962(18) 0.56118(15) 0.0365(5) Uani 1 1 d . . . . .
N2 N 0.3602(2) 0.02550(19) 0.58320(17) 0.0416(5) Uani 1 1 d . . . . .
H2 H 0.3453 -0.0478 0.5820 0.050 Uiso 1 1 calc R . . . .
N3 N 0.6844(3) 0.13878(18) 0.78285(15) 0.0368(5) Uani 1 1 d . . . . .
H3A H 0.6555 0.0978 0.8253 0.044 Uiso 1 1 calc R . . . .
N4 N 0.7807(2) 0.26469(19) 0.64840(14) 0.0363(5) Uani 1 1 d . . . . .
H4A H 0.8069 0.3060 0.6053 0.044 Uiso 1 1 calc R . . . .
N5 N 1.0857(2) 0.2918(2) 0.74556(14) 0.0362(5) Uani 1 1 d . . . . .
H5 H 1.0875 0.3079 0.6894 0.043 Uiso 1 1 calc R . . . .
N6 N 1.1448(2) 0.2183(2) 0.87874(14) 0.0349(5) 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 2.2075(17) . ?
Mn1 O2 2.2622(17) 3_566 ?
Mn1 O3 2.1827(16) . ?
Mn1 O4 2.1845(17) 3_666 ?
Mn1 N1 2.212(2) . ?
Mn1 N6 2.195(2) 4_465 ?
O1 C1 1.258(3) . ?
O2 Mn1 2.2622(17) 3_566 ?
O2 C1 1.233(3) . ?
O3 C2 1.251(3) . ?
O4 Mn1 2.1846(17) 3_666 ?
O4 C2 1.244(3) . ?
O5 C8 1.221(4) . ?
O6 C9 1.229(3) . ?
C1 C1 1.554(4) 3_566 ?
C2 C2 1.564(4) 3_666 ?
C3 H3 0.9300 . ?
C3 N1 1.308(3) . ?
C3 N2 1.330(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.358(4) . ?
C4 N1 1.375(4) . ?
C5 C6 1.497(4) . ?
C5 N2 1.361(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.529(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.522(4) . ?
C7 N3 1.452(3) . ?
C8 N4 1.330(4) . ?
C9 C10 1.512(3) . ?
C9 N3 1.323(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.545(3) . ?
C10 N4 1.449(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.487(3) . ?
C12 C13 1.356(3) . ?
C12 N5 1.371(3) . ?
C13 H13 0.9300 . ?
C13 N6 1.380(3) . ?
C14 H14 0.9300 . ?
C14 N5 1.340(3) . ?
C14 N6 1.315(3) . ?
N2 H2 0.8600 . ?
N3 H3A 0.8600 . ?
N4 H4A 0.8600 . ?
N5 H5 0.8600 . ?
N6 Mn1 2.195(2) 4_666 ?

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 O2 73.08(6) . 3_566 ?
O1 Mn1 N1 94.23(8) . . ?
O3 Mn1 O1 101.22(6) . . ?
O3 Mn1 O2 90.16(7) . 3_566 ?
O3 Mn1 N1 89.91(7) . . ?
O3 Mn1 N6 166.09(7) . 4_465 ?
O4 Mn1 O1 158.30(7) 3_666 . ?
O4 Mn1 O2 85.33(7) 3_666 3_566 ?
O4 Mn1 O3 76.15(6) 3_666 . ?
O4 Mn1 N1 107.22(8) 3_666 . ?
O4 Mn1 N6 89.99(7) 3_666 4_465 ?
N1 Mn1 O2 167.07(8) . 3_566 ?
N6 Mn1 O1 92.10(7) 4_465 . ?
N6 Mn1 O2 89.89(8) 4_465 3_566 ?
N6 Mn1 N1 93.13(8) 4_465 . ?
C1 O1 Mn1 116.11(14) . . ?
C1 O2 Mn1 114.91(14) . 3_566 ?
C2 O3 Mn1 115.02(13) . . ?
C2 O4 Mn1 114.94(14) . 3_666 ?
O1 C1 C1 116.2(2) . 3_566 ?
O2 C1 O1 127.2(2) . . ?
O2 C1 C1 116.6(2) . 3_566 ?
O3 C2 C2 116.7(2) . 3_666 ?
O4 C2 O3 126.1(2) . . ?
O4 C2 C2 117.2(2) . 3_666 ?
N1 C3 H3 124.3 . . ?
N1 C3 N2 111.4(2) . . ?
N2 C3 H3 124.3 . . ?
C5 C4 H4 124.5 . . ?
C5 C4 N1 111.0(2) . . ?
N1 C4 H4 124.5 . . ?
C4 C5 C6 135.5(2) . . ?
C4 C5 N2 104.0(2) . . ?
N2 C5 C6 120.4(2) . . ?
C5 C6 H6A 108.3 . . ?
C5 C6 H6B 108.3 . . ?
C5 C6 C7 115.8(2) . . ?
H6A C6 H6B 107.4 . . ?
C7 C6 H6A 108.3 . . ?
C7 C6 H6B 108.3 . . ?
C6 C7 H7 106.9 . . ?
C8 C7 C6 111.1(2) . . ?
C8 C7 H7 106.9 . . ?
N3 C7 C6 111.2(2) . . ?
N3 C7 H7 106.9 . . ?
N3 C7 C8 113.4(2) . . ?
O5 C8 C7 119.2(3) . . ?
O5 C8 N4 123.2(3) . . ?
N4 C8 C7 117.6(2) . . ?
O6 C9 C10 119.7(2) . . ?
O6 C9 N3 121.9(2) . . ?
N3 C9 C10 118.4(2) . . ?
C9 C10 H10 107.7 . . ?
C9 C10 C11 110.5(2) . . ?
C11 C10 H10 107.7 . . ?
N4 C10 C9 113.4(2) . . ?
N4 C10 H10 107.7 . . ?
N4 C10 C11 109.8(2) . . ?
C10 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 C10 112.7(2) . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C13 C12 C11 130.9(2) . . ?
C13 C12 N5 105.5(2) . . ?
N5 C12 C11 123.6(2) . . ?
C12 C13 H13 125.2 . . ?
C12 C13 N6 109.7(2) . . ?
N6 C13 H13 125.2 . . ?
N5 C14 H14 124.6 . . ?
N6 C14 H14 124.6 . . ?
N6 C14 N5 110.9(2) . . ?
C3 N1 Mn1 128.21(18) . . ?
C3 N1 C4 104.6(2) . . ?
C4 N1 Mn1 125.26(18) . . ?
C3 N2 C5 109.0(2) . . ?
C3 N2 H2 125.5 . . ?
C5 N2 H2 125.5 . . ?
C7 N3 H3A 115.8 . . ?
C9 N3 C7 128.3(2) . . ?
C9 N3 H3A 115.8 . . ?
C8 N4 C10 128.5(2) . . ?
C8 N4 H4A 115.7 . . ?
C10 N4 H4A 115.7 . . ?
C12 N5 H5 125.9 . . ?
C14 N5 C12 108.2(2) . . ?
C14 N5 H5 125.9 . . ?
C13 N6 Mn1 124.78(17) . 4_666 ?
C14 N6 Mn1 129.35(18) . 4_666 ?
C14 N6 C13 105.9(2) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
