# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_Q86
_database_code_depnum_ccdc_archive 'CCDC 1509249'
_audit_update_record             
;
2016-12-15 deposited with the CCDC.
2016-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H4 Mn N4'
_chemical_formula_weight         187.07

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           66
_space_group_name_H-M_alt        'C c c m'
_space_group_name_Hall           '-C 2 2c'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.1570(14)
_cell_length_b                   12.806(3)
_cell_length_c                   7.8560(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     720.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    4050
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      29.56

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    1.761
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8165
_exptl_absorpt_correction_T_max  0.8720
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4050
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.182
_diffrn_reflns_theta_max         29.563
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             530
_reflns_number_gt                453
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0381P)²+0.3264P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         530
_refine_ls_number_parameters     32
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0249
_refine_ls_wR_factor_ref         0.0699
_refine_ls_wR_factor_gt          0.0668
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.2500 0.2500 0.5000 0.02320(17) Uani 1 4 d S T P . .
C1 C 0.05557(19) 0.19145(12) 0.3012(2) 0.0358(4) Uani 0.5 1 d . . P . .
N1 N 0.05557(19) 0.19145(12) 0.3012(2) 0.0358(4) Uani 0.5 1 d . . P . .
N2 N 0.0917(2) 0.40568(14) 0.5000 0.0304(4) Uani 1 2 d S T P . .
C2 C -0.0910(3) 0.41149(18) 0.5000 0.0415(6) Uani 1 2 d S T P . .
H2 H -0.1607 0.3502 0.5000 0.050 Uiso 1 2 calc R U P . .
C3 C 0.1811(3) 0.4953(2) 0.5000 0.0421(6) Uani 1 2 d S T P . .
H3 H 0.3110 0.4948 0.5000 0.051 Uiso 1 2 calc R U P . .


_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 C1 2.2220(15) . ?
Mn1 N1 2.2220(15) 13_556 ?
Mn1 C1 2.2220(15) 13_556 ?
Mn1 N1 2.2220(15) 10_556 ?
Mn1 C1 2.2220(15) 6 ?
Mn1 C1 2.2220(15) 10_556 ?
Mn1 N1 2.2220(15) 6 ?
Mn1 N2 2.2931(17) . ?
Mn1 N2 2.2931(17) 13_556 ?
C1 N1 1.131(3) 3 ?
C1 C1 1.131(3) 3 ?
N2 C2 1.309(3) . ?
N2 C3 1.314(3) . ?
C2 C3 1.357(3) 9_566 ?
C3 C2 1.357(3) 9_566 ?

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
C1 Mn1 N1 180.0 . 13_556 ?
C1 Mn1 C1 180.0 . 13_556 ?
N1 Mn1 C1 0.0 13_556 13_556 ?
C1 Mn1 N1 89.3 . 10_556 ?
N1 Mn1 N1 90.70(8) 13_556 10_556 ?
C1 Mn1 N1 90.70(8) 13_556 10_556 ?
C1 Mn1 C1 90.70(8) . 6 ?
N1 Mn1 C1 89.3 13_556 6 ?
C1 Mn1 C1 89.30(8) 13_556 6 ?
N1 Mn1 C1 180.0 10_556 6 ?
C1 Mn1 C1 89.30(8) . 10_556 ?
N1 Mn1 C1 90.7 13_556 10_556 ?
C1 Mn1 C1 90.70(8) 13_556 10_556 ?
N1 Mn1 C1 0.0 10_556 10_556 ?
C1 Mn1 C1 180.00(7) 6 10_556 ?
C1 Mn1 N1 90.7 . 6 ?
N1 Mn1 N1 89.30(8) 13_556 6 ?
C1 Mn1 N1 89.30(8) 13_556 6 ?
N1 Mn1 N1 180.0 10_556 6 ?
C1 Mn1 N1 0.00(9) 6 6 ?
C1 Mn1 N1 180.0 10_556 6 ?
C1 Mn1 N2 89.08(5) . . ?
N1 Mn1 N2 90.92(5) 13_556 . ?
C1 Mn1 N2 90.92(5) 13_556 . ?
N1 Mn1 N2 89.08(5) 10_556 . ?
C1 Mn1 N2 90.92(5) 6 . ?
C1 Mn1 N2 89.08(5) 10_556 . ?
N1 Mn1 N2 90.92(5) 6 . ?
C1 Mn1 N2 90.92(5) . 13_556 ?
N1 Mn1 N2 89.08(5) 13_556 13_556 ?
C1 Mn1 N2 89.08(5) 13_556 13_556 ?
N1 Mn1 N2 90.92(5) 10_556 13_556 ?
C1 Mn1 N2 89.08(5) 6 13_556 ?
C1 Mn1 N2 90.92(5) 10_556 13_556 ?
N1 Mn1 N2 89.08(5) 6 13_556 ?
N2 Mn1 N2 180.0 . 13_556 ?
N1 C1 C1 0.0 3 3 ?
N1 C1 Mn1 160.07(5) 3 . ?
C1 C1 Mn1 160.07(5) 3 . ?
C2 N2 C3 115.88(19) . . ?
C2 N2 Mn1 122.87(16) . . ?
C3 N2 Mn1 121.25(14) . . ?
N2 C2 C3 121.6(2) . 9_566 ?
N2 C3 C2 122.5(2) . 9_566 ?

_refine_diff_density_max         0.348
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_QS72
_database_code_depnum_ccdc_archive 'CCDC 1509248'
_audit_update_record             
;
2016-12-15 deposited with the CCDC.
2016-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25.14 H20.28 Mn2 N8 O'
_chemical_formula_weight         560.32

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3630(17)
_cell_length_b                   12.827(3)
_cell_length_c                   12.987(3)
_cell_angle_alpha                78.01(3)
_cell_angle_beta                 77.50(3)
_cell_angle_gamma                71.85(3)
_cell_volume                     1277.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9605
_cell_measurement_theta_min      1.62
_cell_measurement_theta_max      23.27

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    1.024
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8617
_exptl_absorpt_correction_T_max  0.9227
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9605
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.625
_diffrn_reflns_theta_max         23.274
_diffrn_reflns_theta_full        23.274
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.934
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.934
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.934
_reflns_number_total             3449
_reflns_number_gt                2835
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0840P)²+3.0904P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3449
_refine_ls_number_parameters     338
_refine_ls_number_restraints     379
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1549
_refine_ls_wR_factor_gt          0.1435
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn -0.10437(10) 1.22012(6) 0.04146(6) 0.0214(3) Uani 1 1 d . . . . .
Mn2 Mn 0.36189(9) 1.09808(6) 0.30991(6) 0.0204(3) Uani 1 1 d . . . . .
C1 C 0.4773(6) 1.0197(4) 0.4595(4) 0.0260(10) Uani 0.5 1 d . U P . .
N1 N 0.4773(6) 1.0197(4) 0.4595(4) 0.0260(10) Uani 0.5 1 d . . P . .
O1 O 0.1621(5) 1.0131(3) 0.3876(3) 0.0283(9) Uani 1 1 d . U . . .
H1 H 0.1982 0.9514 0.4211 0.030(17) Uiso 1 1 calc R . . . .
C2 C 0.0153(14) 1.0160(9) 0.3449(9) 0.040(2) Uani 0.570(10) 1 d . U P . .
H2A H -0.0165 1.0904 0.3055 0.048 Uiso 0.570(10) 1 calc R U P . .
H2B H -0.0728 1.0152 0.4072 0.048 Uiso 0.570(10) 1 calc R U P . .
N2 N 0.2149(5) 1.2536(3) 0.3852(3) 0.0228(10) Uani 1 1 d . . . . .
C3 C 0.6759(7) 1.1985(4) 0.1582(4) 0.0218(11) Uani 1 1 d . . . . .
N3 N 0.5658(6) 1.1771(4) 0.2191(4) 0.0302(11) Uani 1 1 d . . . . .
C4 C -0.0205(13) 0.9400(8) 0.2721(8) 0.030(2) Uani 0.570(10) 1 d . U P . .
H4A H 0.0840 0.9073 0.2281 0.045 Uiso 0.570(10) 1 calc R U P . .
H4B H -0.1023 0.9853 0.2277 0.045 Uiso 0.570(10) 1 calc R U P . .
H4C H -0.0644 0.8824 0.3174 0.045 Uiso 0.570(10) 1 calc R U P . .
N4 N 0.4972(5) 0.9480(4) 0.2223(3) 0.0256(10) Uani 1 1 d . . . . .
C5 C 0.1095(7) 1.1945(4) 0.1231(4) 0.0262(10) Uani 1 1 d . U . . .
N5 N 0.2062(6) 1.1723(4) 0.1791(4) 0.0283(11) Uani 1 1 d . . . . .
C6 C -0.1449(7) 1.2863(4) -0.1209(4) 0.0239(11) Uani 1 1 d . U . . .
N6 N -0.1647(7) 1.3184(5) -0.2061(4) 0.0444(14) Uani 1 1 d . . . . .
C7 C -0.0208(7) 1.0439(4) 0.0105(4) 0.0308(10) Uani 0.5 1 d . U P . .
N7 N -0.0208(7) 1.0439(4) 0.0105(4) 0.0308(10) Uani 0.5 1 d . . P . .
C8 C 0.2076(7) 1.3547(4) 0.3290(4) 0.0279(10) Uani 1 1 d . U . . .
H8 H 0.2616 1.3595 0.2584 0.033 Uiso 1 1 calc R U . . .
N8 N 0.8182(6) 0.4118(3) 0.0697(3) 0.0254(10) Uani 1 1 d . . . . .
C9 C 0.1244(7) 1.4521(4) 0.3701(4) 0.0272(10) Uani 1 1 d . U . . .
H9 H 0.1218 1.5202 0.3271 0.033 Uiso 1 1 calc R U . . .
N9 N 0.6995(7) 0.2086(4) 0.5339(4) 0.0393(13) Uani 1 1 d . . . . .
C10 C 0.0443(6) 1.4479(4) 0.4763(4) 0.0214(9) Uani 1 1 d . U . . .
C11 C 0.0505(7) 1.3431(4) 0.5344(4) 0.0270(10) Uani 1 1 d . U . . .
H11 H -0.0024 1.3358 0.6052 0.032 Uiso 1 1 calc R U . . .
C12 C 0.1350(7) 1.2504(4) 0.4870(4) 0.0274(10) Uani 1 1 d . U . . .
H12 H 0.1370 1.1814 0.5277 0.033 Uiso 1 1 calc R U . . .
C13 C 0.4379(7) 0.9222(5) 0.1458(4) 0.0312(10) Uani 1 1 d . U . . .
H13 H 0.3480 0.9746 0.1165 0.037 Uiso 1 1 calc R U . . .
C14 C 0.5037(7) 0.8216(4) 0.1084(5) 0.0324(10) Uani 1 1 d . U . . .
H14 H 0.4569 0.8072 0.0559 0.039 Uiso 1 1 calc R U . . .
C15 C 0.6387(7) 0.7427(4) 0.1486(5) 0.0321(9) Uani 1 1 d . U . . .
C16 C 0.7061(8) 0.7713(5) 0.2246(5) 0.0372(10) Uani 1 1 d . U . . .
H16 H 0.7993 0.7217 0.2529 0.045 Uiso 1 1 calc R U . . .
C17 C 0.6333(7) 0.8739(5) 0.2573(5) 0.0340(10) Uani 1 1 d . U . . .
H17 H 0.6819 0.8924 0.3065 0.041 Uiso 1 1 calc R U . . .
C18 C 0.7361(8) 0.4983(5) 0.0055(5) 0.0389(11) Uani 1 1 d . U . . .
H18 H 0.7163 0.4846 -0.0575 0.047 Uiso 1 1 calc R U . . .
C19 C 0.6787(8) 0.6059(5) 0.0258(5) 0.0396(10) Uani 1 1 d . U . . .
H19 H 0.6233 0.6624 -0.0227 0.048 Uiso 1 1 calc R U . . .
C20 C 0.7045(7) 0.6286(4) 0.1192(5) 0.0317(9) Uani 1 1 d . U . . .
C21 C 0.7904(8) 0.5411(5) 0.1848(5) 0.0419(10) Uani 1 1 d . U . . .
H21 H 0.8125 0.5524 0.2482 0.050 Uiso 1 1 calc R U . . .
C22 C 0.8442(8) 0.4363(5) 0.1570(5) 0.0429(12) Uani 1 1 d . U . . .
H22 H 0.9031 0.3788 0.2032 0.051 Uiso 1 1 calc R U . . .
C23 C 0.6416(9) 0.2632(5) 0.4448(5) 0.0469(12) Uani 1 1 d . U . . .
H23 H 0.6526 0.2231 0.3905 0.056 Uiso 1 1 calc R U . . .
C24 C 0.5660(9) 0.3761(5) 0.4280(5) 0.0452(12) Uani 1 1 d . U . . .
H24 H 0.5308 0.4099 0.3630 0.054 Uiso 1 1 calc R U . . .
C25 C 0.5422(8) 0.4390(5) 0.5065(5) 0.0345(11) Uani 1 1 d . U . . .
C26 C 0.5971(8) 0.3807(5) 0.6009(5) 0.0383(11) Uani 1 1 d . U . . .
H26 H 0.5820 0.4179 0.6580 0.046 Uiso 1 1 calc R U . . .
C27 C 0.6736(8) 0.2684(5) 0.6107(5) 0.0389(12) Uani 1 1 d . U . . .
H27 H 0.7093 0.2322 0.6751 0.047 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 C6 2.161(5) . ?
Mn1 C3 2.166(6) 1_455 ?
Mn1 C5 2.177(6) . ?
Mn1 C7 2.243(5) . ?
Mn1 N8 2.424(4) 1_465 ?
Mn2 O1 2.224(4) . ?
Mn2 N5 2.236(5) . ?
Mn2 N3 2.244(5) . ?
Mn2 C1 2.261(5) . ?
Mn2 N2 2.282(4) . ?
Mn2 N4 2.298(4) . ?
C1 N1 1.158(9) 2_676 ?
C1 C1 1.158(9) 2_676 ?
O1 C2 1.440(11) . ?
C2 C4 1.618(15) . ?
N2 C8 1.340(7) . ?
N2 C12 1.345(7) . ?
C3 N3 1.140(7) . ?
C3 Mn1 2.166(6) 1_655 ?
N4 C17 1.332(7) . ?
N4 C13 1.340(7) . ?
C5 N5 1.135(7) . ?
C6 N6 1.126(7) . ?
C7 N7 1.144(10) 2_575 ?
C7 C7 1.144(10) 2_575 ?
C8 C9 1.379(7) . ?
N8 C22 1.315(7) . ?
N8 C18 1.336(7) . ?
N8 Mn1 2.424(4) 1_645 ?
C9 C10 1.396(7) . ?
N9 C27 1.322(8) . ?
N9 C23 1.326(8) . ?
C10 C11 1.389(8) . ?
C10 C10 1.496(10) 2_586 ?
C11 C12 1.372(7) . ?
C13 C14 1.380(8) . ?
C14 C15 1.377(8) . ?
C15 C16 1.395(8) . ?
C15 C20 1.494(8) . ?
C16 C17 1.380(8) . ?
C18 C19 1.374(8) . ?
C19 C20 1.379(8) . ?
C20 C21 1.366(8) . ?
C21 C22 1.376(8) . ?
C23 C24 1.379(9) . ?
C24 C25 1.373(9) . ?
C25 C26 1.386(8) . ?
C25 C25 1.493(11) 2_666 ?
C26 C27 1.373(8) . ?

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
C6 Mn1 C3 117.4(2) . 1_455 ?
C6 Mn1 C5 132.5(2) . . ?
C3 Mn1 C5 109.3(2) 1_455 . ?
C6 Mn1 C7 93.01(19) . . ?
C3 Mn1 C7 93.93(19) 1_455 . ?
C5 Mn1 C7 92.7(2) . . ?
C6 Mn1 N8 86.08(17) . 1_465 ?
C3 Mn1 N8 88.83(18) 1_455 1_465 ?
C5 Mn1 N8 86.01(17) . 1_465 ?
C7 Mn1 N8 177.21(18) . 1_465 ?
O1 Mn2 N5 86.71(16) . . ?
O1 Mn2 N3 175.06(15) . . ?
N5 Mn2 N3 90.49(17) . . ?
O1 Mn2 C1 84.36(17) . . ?
N5 Mn2 C1 170.28(18) . . ?
N3 Mn2 C1 98.68(18) . . ?
O1 Mn2 N2 92.04(15) . . ?
N5 Mn2 N2 86.27(16) . . ?
N3 Mn2 N2 91.84(16) . . ?
C1 Mn2 N2 90.22(16) . . ?
O1 Mn2 N4 87.86(15) . . ?
N5 Mn2 N4 88.87(16) . . ?
N3 Mn2 N4 88.02(17) . . ?
C1 Mn2 N4 94.61(17) . . ?
N2 Mn2 N4 175.13(15) . . ?
N1 C1 C1 0.0 2_676 2_676 ?
N1 C1 Mn2 174.2(6) 2_676 . ?
C1 C1 Mn2 174.2(6) 2_676 . ?
C2 O1 Mn2 126.7(5) . . ?
O1 C2 C4 133.9(9) . . ?
C8 N2 C12 116.1(4) . . ?
C8 N2 Mn2 120.6(3) . . ?
C12 N2 Mn2 123.2(3) . . ?
N3 C3 Mn1 173.8(4) . 1_655 ?
C3 N3 Mn2 163.7(4) . . ?
C17 N4 C13 116.6(4) . . ?
C17 N4 Mn2 118.4(3) . . ?
C13 N4 Mn2 124.5(4) . . ?
N5 C5 Mn1 168.7(5) . . ?
C5 N5 Mn2 165.9(5) . . ?
N6 C6 Mn1 178.4(5) . . ?
N7 C7 C7 0.0 2_575 2_575 ?
N7 C7 Mn1 176.5(6) 2_575 . ?
C7 C7 Mn1 176.5(6) 2_575 . ?
N2 C8 C9 123.7(5) . . ?
C22 N8 C18 114.8(5) . . ?
C22 N8 Mn1 120.4(4) . 1_645 ?
C18 N8 Mn1 124.6(3) . 1_645 ?
C8 C9 C10 119.7(5) . . ?
C27 N9 C23 115.9(5) . . ?
C11 C10 C9 116.6(5) . . ?
C11 C10 C10 122.5(6) . 2_586 ?
C9 C10 C10 120.9(6) . 2_586 ?
C12 C11 C10 119.9(5) . . ?
N2 C12 C11 123.9(5) . . ?
N4 C13 C14 123.2(5) . . ?
C15 C14 C13 120.0(5) . . ?
C14 C15 C16 116.9(5) . . ?
C14 C15 C20 122.5(5) . . ?
C16 C15 C20 120.5(5) . . ?
C17 C16 C15 119.3(5) . . ?
N4 C17 C16 123.7(5) . . ?
N8 C18 C19 124.9(5) . . ?
C18 C19 C20 118.9(5) . . ?
C21 C20 C19 116.8(5) . . ?
C21 C20 C15 121.4(5) . . ?
C19 C20 C15 121.8(5) . . ?
C20 C21 C22 120.0(5) . . ?
N8 C22 C21 124.6(5) . . ?
N9 C23 C24 123.8(6) . . ?
C25 C24 C23 120.6(6) . . ?
C24 C25 C26 115.2(5) . . ?
C24 C25 C25 122.8(6) . 2_666 ?
C26 C25 C25 121.9(7) . 2_666 ?
C27 C26 C25 120.6(6) . . ?
N9 C27 C26 123.8(6) . . ?

_refine_diff_density_max         0.633
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.103

