# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_rt
_database_code_depnum_ccdc_archive 'CCDC 1057529'
_audit_update_record             
;
2015-04-02 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H8 Mn N2 O6'
_chemical_formula_weight         259.08

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'
Cl Cl 0.1484 0.1585 '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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   ' P 21/n'
_symmetry_space_group_name_HALL  ' -P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.345(7)
_cell_length_b                   12.481(7)
_cell_length_c                   12.850(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 133.15(2)
_cell_angle_gamma                90.00
_cell_volume                     1979.9(1)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048
_exptl_absorpt_coefficient_mu    1.344
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.743
_exptl_absorpt_correction_T_max  0.750
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13814
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4489
_reflns_number_gt                3301
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0535P)²+0.8383P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4489
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1295
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.156
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.73393(4) 0.25238(3) 0.49340(3) 0.01831(13) Uani 1 1 d . . .
Mn2 Mn 0.23223(4) 0.25285(3) -0.00786(3) 0.01853(13) Uani 1 1 d . . .
O1 O 0.5321(3) 0.2409(2) 0.32990(17) 0.0508(7) Uani 1 1 d . . .
O2 O 0.7804(3) 0.08799(17) 0.47997(18) 0.0447(6) Uani 1 1 d . . .
O3 O 0.6081(2) 0.18710(17) 0.52983(16) 0.0336(5) Uani 1 1 d . . .
O4 O 0.9300(3) 0.2406(2) 0.65776(17) 0.0526(7) Uani 1 1 d . . .
O5 O 0.6913(3) 0.41457(16) 0.50937(18) 0.0378(5) Uani 1 1 d . . .
O6 O 0.8628(3) 0.31193(19) 0.4615(2) 0.0476(6) Uani 1 1 d . . .
O7 O 0.3663(3) 0.23404(19) 0.15987(16) 0.0424(6) Uani 1 1 d . . .
O8 O 0.8284(2) -0.08496(15) 0.50273(17) 0.0347(5) Uani 1 1 d . . .
O9 O 0.4244(2) 0.18292(18) 0.52541(17) 0.0382(5) Uani 1 1 d . . .
O10 O 1.1063(3) 0.2515(2) 0.82743(16) 0.0480(7) Uani 1 1 d . . .
O11 O 0.7121(2) 0.59038(15) 0.51855(16) 0.0330(5) Uani 1 1 d . . .
O12 O 1.0601(2) 0.30784(18) 0.48196(19) 0.0423(6) Uani 1 1 d . . .
C1 C 0.4807(3) 0.2709(3) 0.2445(2) 0.0340(7) Uani 1 1 d . . .
H1 H 0.5307 0.3251 0.2428 0.041 Uiso 1 1 calc R . .
C2 C 0.8031(4) 0.0027(2) 0.5226(3) 0.0323(7) Uani 1 1 d . . .
H2 H 0.8015 0.0028 0.5745 0.039 Uiso 1 1 calc R . .
C3 C 0.4857(3) 0.2163(3) 0.4964(2) 0.0310(7) Uani 1 1 d . . .
H3 H 0.4352 0.2682 0.4445 0.037 Uiso 1 1 calc R . .
C4 C 0.9887(3) 0.2813(3) 0.7420(2) 0.0325(7) Uani 1 1 d . . .
H4 H 0.9405 0.3392 0.7413 0.039 Uiso 1 1 calc R . .
C5 C 0.7127(4) 0.5011(2) 0.4872(2) 0.0293(6) Uani 1 1 d . . .
H5 H 0.7306 0.4995 0.4439 0.035 Uiso 1 1 calc R . .
C6 C 0.9474(3) 0.2700(3) 0.4559(3) 0.0355(7) Uani 1 1 d . . .
H6 H 0.9226 0.2011 0.4285 0.043 Uiso 1 1 calc R . .
N1 N 0.7779(3) 0.5400(3) 0.8255(2) 0.0459(7) Uani 1 1 d . . .
H1A H 0.8074 0.5542 0.8849 0.055 Uiso 1 1 calc R . .
N2 N 0.7495(4) 0.5496(3) 0.6932(3) 0.0540(9) Uani 1 1 d . . .
C7 C 0.6870(5) 0.4594(3) 0.7627(3) 0.0550(10) Uani 1 1 d . . .
H7 H 0.6446 0.4097 0.7751 0.066 Uiso 1 1 calc R . .
C9 C 0.8143(4) 0.5934(3) 0.7821(3) 0.0525(10) Uani 1 1 d . . .
H9 H 0.8764 0.6529 0.8102 0.063 Uiso 1 1 calc R . .
C8 C 0.6688(5) 0.4639(4) 0.6786(3) 0.0623(11) Uani 1 1 d . . .
H8 H 0.6124 0.4178 0.6218 0.075 Uiso 1 1 calc R . .
N3 N 0.7379(4) 0.9219(2) 0.7845(2) 0.0438(7) Uani 1 1 d . . .
N4 N 0.7210(4) 1.0444(2) 0.6923(2) 0.0467(8) Uani 1 1 d . . .
H4A H 0.6844 1.0882 0.6421 0.056 Uiso 1 1 calc R . .
C10 C 0.8758(4) 0.9600(3) 0.8369(3) 0.0447(8) Uani 1 1 d . . .
H10 H 0.9630 0.9372 0.9019 0.054 Uiso 1 1 calc R . .
C11 C 0.6434(4) 0.9752(3) 0.6953(3) 0.0529(10) Uani 1 1 d . . .
H11 H 0.5412 0.9653 0.6442 0.063 Uiso 1 1 calc R . .
C12 C 0.8644(4) 1.0367(3) 0.7786(3) 0.0478(9) Uani 1 1 d . . .
H12 H 0.9417 1.0768 0.7952 0.057 Uiso 1 1 calc R . .
H2A H 0.743(5) 0.569(4) 0.637(4) 0.093(16) Uiso 1 1 d . . .
H3A H 0.706(6) 0.865(5) 0.802(4) 0.12(2) 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
Mn1 O6 2.151(2) . ?
Mn1 O5 2.158(2) . ?
Mn1 O4 2.164(2) . ?
Mn1 O1 2.171(2) . ?
Mn1 O2 2.186(2) . ?
Mn1 O3 2.203(2) . ?
Mn2 O12 2.144(2) 4_465 ?
Mn2 O10 2.162(2) 1_454 ?
Mn2 O9 2.171(2) 4_565 ?
Mn2 O8 2.182(2) 2_655 ?
Mn2 O11 2.190(2) 2_645 ?
Mn2 O7 2.201(2) . ?
O1 C1 1.225(4) . ?
O2 C2 1.220(3) . ?
O3 C3 1.243(3) . ?
O4 C4 1.231(4) . ?
O5 C5 1.237(3) . ?
O6 C6 1.231(4) . ?
O7 C1 1.245(4) . ?
O8 C2 1.251(3) . ?
O8 Mn2 2.182(2) 2_645 ?
O9 C3 1.240(3) . ?
O9 Mn2 2.171(2) 4_566 ?
O10 C4 1.234(4) . ?
O10 Mn2 2.162(2) 1_656 ?
O11 C5 1.245(3) . ?
O11 Mn2 2.190(2) 2_655 ?
O12 C6 1.223(4) . ?
O12 Mn2 2.144(2) 4_666 ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N1 C9 1.305(5) . ?
N1 C7 1.341(5) . ?
N1 H1A 0.8600 . ?
N2 C9 1.296(5) . ?
N2 C8 1.361(6) . ?
N2 H2A 0.97(5) . ?
C7 C8 1.338(6) . ?
C7 H7 0.9300 . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
N3 C11 1.329(5) . ?
N3 C10 1.351(5) . ?
N3 H3A 0.96(6) . ?
N4 C11 1.317(5) . ?
N4 C12 1.332(5) . ?
N4 H4A 0.8600 . ?
C10 C12 1.340(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

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
O6 Mn1 O5 90.00(9) . . ?
O6 Mn1 O4 91.36(12) . . ?
O5 Mn1 O4 92.18(9) . . ?
O6 Mn1 O1 93.33(11) . . ?
O5 Mn1 O1 94.27(10) . . ?
O4 Mn1 O1 172.02(10) . . ?
O6 Mn1 O2 90.02(9) . . ?
O5 Mn1 O2 179.06(9) . . ?
O4 Mn1 O2 86.88(9) . . ?
O1 Mn1 O2 86.67(10) . . ?
O6 Mn1 O3 177.96(8) . . ?
O5 Mn1 O3 91.46(8) . . ?
O4 Mn1 O3 87.16(11) . . ?
O1 Mn1 O3 87.98(10) . . ?
O2 Mn1 O3 88.49(9) . . ?
O12 Mn2 O10 97.10(10) 4_465 1_454 ?
O12 Mn2 O9 172.01(8) 4_465 4_565 ?
O10 Mn2 O9 90.86(10) 1_454 4_565 ?
O12 Mn2 O8 89.01(9) 4_465 2_655 ?
O10 Mn2 O8 96.38(9) 1_454 2_655 ?
O9 Mn2 O8 89.36(9) 4_565 2_655 ?
O12 Mn2 O11 90.99(9) 4_465 2_645 ?
O10 Mn2 O11 81.76(9) 1_454 2_645 ?
O9 Mn2 O11 90.89(9) 4_565 2_645 ?
O8 Mn2 O11 178.13(8) 2_655 2_645 ?
O12 Mn2 O7 82.33(10) 4_465 . ?
O10 Mn2 O7 173.16(9) 1_454 . ?
O9 Mn2 O7 89.86(9) 4_565 . ?
O8 Mn2 O7 90.43(9) 2_655 . ?
O11 Mn2 O7 91.42(9) 2_645 . ?
C1 O1 Mn1 140.4(2) . . ?
C2 O2 Mn1 136.0(2) . . ?
C3 O3 Mn1 128.6(2) . . ?
C4 O4 Mn1 141.6(2) . . ?
C5 O5 Mn1 130.9(2) . . ?
C6 O6 Mn1 133.9(2) . . ?
C1 O7 Mn2 139.9(2) . . ?
C2 O8 Mn2 129.9(2) . 2_645 ?
C3 O9 Mn2 128.8(2) . 4_566 ?
C4 O10 Mn2 143.3(2) . 1_656 ?
C5 O11 Mn2 133.8(2) . 2_655 ?
C6 O12 Mn2 134.6(2) . 4_666 ?
O1 C1 O7 124.7(3) . . ?
O1 C1 H1 117.6 . . ?
O7 C1 H1 117.6 . . ?
O2 C2 O8 126.0(3) . . ?
O2 C2 H2 117.0 . . ?
O8 C2 H2 117.0 . . ?
O9 C3 O3 126.4(3) . . ?
O9 C3 H3 116.8 . . ?
O3 C3 H3 116.8 . . ?
O4 C4 O10 125.3(3) . . ?
O4 C4 H4 117.3 . . ?
O10 C4 H4 117.3 . . ?
O5 C5 O11 125.0(3) . . ?
O5 C5 H5 117.5 . . ?
O11 C5 H5 117.5 . . ?
O12 C6 O6 128.0(3) . . ?
O12 C6 H6 116.0 . . ?
O6 C6 H6 116.0 . . ?
C9 N1 C7 109.1(3) . . ?
C9 N1 H1A 125.4 . . ?
C7 N1 H1A 125.4 . . ?
C9 N2 C8 109.1(3) . . ?
C9 N2 H2A 133(3) . . ?
C8 N2 H2A 118(3) . . ?
C8 C7 N1 107.2(4) . . ?
C8 C7 H7 126.4 . . ?
N1 C7 H7 126.4 . . ?
N2 C9 N1 108.6(4) . . ?
N2 C9 H9 125.7 . . ?
N1 C9 H9 125.7 . . ?
C7 C8 N2 106.1(4) . . ?
C7 C8 H8 127.0 . . ?
N2 C8 H8 127.0 . . ?
C11 N3 C10 108.0(3) . . ?
C11 N3 H3A 122(3) . . ?
C10 N3 H3A 130(3) . . ?
C11 N4 C12 110.0(3) . . ?
C11 N4 H4A 125.0 . . ?
C12 N4 H4A 125.0 . . ?
C12 C10 N3 107.7(3) . . ?
C12 C10 H10 126.1 . . ?
N3 C10 H10 126.1 . . ?
N4 C11 N3 107.6(3) . . ?
N4 C11 H11 126.2 . . ?
N3 C11 H11 126.2 . . ?
N4 C12 C10 106.7(3) . . ?
N4 C12 H12 126.6 . . ?
C10 C12 H12 126.6 . . ?

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
O6 Mn1 O1 C1 -14.0(4) . . . . ?
O5 Mn1 O1 C1 76.2(4) . . . . ?
O4 Mn1 O1 C1 -139.9(6) . . . . ?
O2 Mn1 O1 C1 -103.9(4) . . . . ?
O3 Mn1 O1 C1 167.5(4) . . . . ?
O6 Mn1 O2 C2 144.1(4) . . . . ?
O5 Mn1 O2 C2 53(5) . . . . ?
O4 Mn1 O2 C2 52.7(4) . . . . ?
O1 Mn1 O2 C2 -122.6(4) . . . . ?
O3 Mn1 O2 C2 -34.5(4) . . . . ?
O6 Mn1 O3 C3 -180(100) . . . . ?
O5 Mn1 O3 C3 44.7(3) . . . . ?
O4 Mn1 O3 C3 136.8(3) . . . . ?
O1 Mn1 O3 C3 -49.5(3) . . . . ?
O2 Mn1 O3 C3 -136.2(3) . . . . ?
O6 Mn1 O4 C4 111.2(4) . . . . ?
O5 Mn1 O4 C4 21.1(4) . . . . ?
O1 Mn1 O4 C4 -122.9(7) . . . . ?
O2 Mn1 O4 C4 -158.9(4) . . . . ?
O3 Mn1 O4 C4 -70.3(4) . . . . ?
O6 Mn1 O5 C5 11.8(3) . . . . ?
O4 Mn1 O5 C5 103.2(3) . . . . ?
O1 Mn1 O5 C5 -81.5(3) . . . . ?
O2 Mn1 O5 C5 103(5) . . . . ?
O3 Mn1 O5 C5 -169.6(3) . . . . ?
O5 Mn1 O6 C6 168.4(3) . . . . ?
O4 Mn1 O6 C6 76.2(3) . . . . ?
O1 Mn1 O6 C6 -97.3(3) . . . . ?
O2 Mn1 O6 C6 -10.6(3) . . . . ?
O3 Mn1 O6 C6 33(3) . . . . ?
O12 Mn2 O7 C1 -155.3(4) 4_465 . . . ?
O10 Mn2 O7 C1 119.0(8) 1_454 . . . ?
O9 Mn2 O7 C1 23.0(4) 4_565 . . . ?
O8 Mn2 O7 C1 -66.4(4) 2_655 . . . ?
O11 Mn2 O7 C1 113.9(4) 2_645 . . . ?
Mn1 O1 C1 O7 165.9(3) . . . . ?
Mn2 O7 C1 O1 -178.1(3) . . . . ?
Mn1 O2 C2 O8 -179.9(2) . . . . ?
Mn2 O8 C2 O2 -146.5(3) 2_645 . . . ?
Mn2 O9 C3 O3 168.2(2) 4_566 . . . ?
Mn1 O3 C3 O9 -173.7(2) . . . . ?
Mn1 O4 C4 O10 177.1(3) . . . . ?
Mn2 O10 C4 O4 -157.0(3) 1_656 . . . ?
Mn1 O5 C5 O11 -164.6(2) . . . . ?
Mn2 O11 C5 O5 172.4(2) 2_655 . . . ?
Mn2 O12 C6 O6 173.7(3) 4_666 . . . ?
Mn1 O6 C6 O12 -144.7(3) . . . . ?
C9 N1 C7 C8 0.4(5) . . . . ?
C8 N2 C9 N1 -0.5(5) . . . . ?
C7 N1 C9 N2 0.1(5) . . . . ?
N1 C7 C8 N2 -0.7(5) . . . . ?
C9 N2 C8 C7 0.8(5) . . . . ?
C11 N3 C10 C12 -0.2(4) . . . . ?
C12 N4 C11 N3 0.0(4) . . . . ?
C10 N3 C11 N4 0.2(4) . . . . ?
C11 N4 C12 C10 -0.1(4) . . . . ?
N3 C10 C12 N4 0.2(4) . . . . ?

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 H1A O8 0.86 1.95 2.792(4) 167.5 4_566
N1 H1A O2 0.86 2.61 3.138(4) 120.4 4_566
N4 H4A O3 0.86 1.94 2.803(4) 178.0 1_565
N4 H4A O9 0.86 2.63 3.211(4) 126.3 1_565
N2 H2A O11 0.97(5) 1.87(5) 2.829(4) 172(4) .
N3 H3A O7 0.96(6) 1.89(6) 2.851(4) 173(5) 3_666
N3 H3A O1 0.96(6) 2.54(5) 3.180(4) 124(4) 3_666

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.095
####################################################################### 
# 
# 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_ht
_database_code_depnum_ccdc_archive 'CCDC 1057530'
_audit_update_record             
;
2015-05-12 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H8 Mn N2 O6'
_chemical_formula_weight         259.08

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'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P -4 21 m '

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

_cell_length_a                   8.8169(10)
_cell_length_b                   8.8169(10)
_cell_length_c                   6.4562(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     501.89(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    453(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             262
_exptl_absorpt_coefficient_mu    1.326
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      453(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Mercury2 (2x2 bin mode)'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1747
_diffrn_reflns_av_R_equivalents  0.1789
_diffrn_reflns_av_sigmaI/netI    0.1276
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.91
_diffrn_reflns_theta_max         27.45
_reflns_number_total             374
_reflns_number_gt                214
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0850P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_number_reflns         374
_refine_ls_number_parameters     48
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.1174
_refine_ls_R_factor_gt           0.0879
_refine_ls_wR_factor_ref         0.2173
_refine_ls_wR_factor_gt          0.2006
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_restrained_S_all      1.157
_refine_ls_shift/su_max          0.054
_refine_ls_shift/su_mean         0.005

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.5000 0.5000 0.5000 0.0404(8) Uani 1 4 d S . .
C1 C 0.7218(17) 0.2218(17) 0.516(8) 0.115(10) Uani 1 2 d S . .
H1 H 0.7945 0.2943 0.5498 0.139 Uiso 1 2 d SR . .
O1 O 0.6018(7) 0.2768(7) 0.505(2) 0.087(3) Uani 1 1 d . . .
C2 C 0.5000 0.5000 1.0000 0.107(9) Uani 1 4 d S . .
H2 H 0.4363 0.5881 1.0000 0.129 Uiso 0.25 1 d PR . .
O2 O 0.5357(19) 0.487(7) 0.8359(19) 0.065(5) Uani 0.50 1 d P . .
N2 N 0.622(2) 0.049(4) 0.905(4) 0.073(10) Uani 0.25 1 d PGU . .
H2A H 0.7101 0.0525 0.8353 0.087 Uiso 0.25 1 d PR . .
C5 C 0.604(3) -0.010(4) 1.108(4) 0.065(5) Uani 0.25 1 d PGU . .
H5A H 0.6841 -0.0402 1.1999 0.078 Uiso 0.25 1 d PR . .
N1 N 0.446(3) -0.017(4) 1.152(3) 0.065(5) Uani 0.25 1 d PGU . .
H1A H 0.4044 -0.0501 1.2712 0.078 Uiso 0.25 1 d PR . .
C4 C 0.367(2) 0.038(4) 0.976(5) 0.065(5) Uani 0.25 1 d PGU . .
H4A H 0.2591 0.0460 0.9626 0.078 Uiso 0.25 1 d PR . .
C3 C 0.475(3) 0.078(4) 0.823(4) 0.074(13) Uani 0.25 1 d PGU . .
H3A H 0.4535 0.1189 0.6878 0.089 Uiso 0.25 1 d PR . .


_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 2.163(7) 3_566 ?
Mn1 O1 2.163(7) 4_656 ?
Mn1 O1 2.163(7) . ?
Mn1 O1 2.163(7) 2_665 ?
Mn1 O2 2.195(13) 4_656 ?
Mn1 O2 2.195(13) . ?
Mn1 O2 2.195(13) 3_566 ?
Mn1 O2 2.195(13) 2_665 ?
Mn1 Mn1 6.2345(7) 5_656 ?
Mn1 Mn1 6.2345(7) 5_546 ?
Mn1 Mn1 6.2345(7) 5_646 ?
Mn1 Mn1 6.2345(7) 5_556 ?
C1 O1 1.166(8) 8_545 ?
C1 O1 1.166(8) . ?
C1 H1 0.9319 . ?
C2 O2 1.111(12) 3_567 ?
C2 O2 1.111(12) 2_665 ?
C2 O2 1.111(13) 4_657 ?
C2 O2 1.111(13) . ?
C2 H2 0.9584 . ?
O2 O2 0.67(4) 2_665 ?
N2 C3 0.918(11) 8_545 ?
N2 C4 0.90(5) 2_655 ?
N2 N2 0.91(5) 8_545 ?
N2 C5 1.4200 . ?
N2 C3 1.4200 . ?
N2 C3 1.51(7) 2_655 ?
N2 N1 1.73(2) 2_655 ?
N2 C4 1.658(16) 7 ?
N2 C4 1.826(17) 8_545 ?
N2 N1 1.85(2) 7 ?
N2 C5 1.82(4) 8_545 ?
N2 C3 1.85(5) 7 ?
N2 H2A 0.8984 . ?
C5 N1 0.58(5) 2_655 ?
C5 C5 1.17(6) 7 ?
C5 C4 0.923(13) 2_655 ?
C5 N1 0.994(9) 7 ?
C5 N1 1.17(3) 8_545 ?
C5 C4 1.498(12) 8_545 ?
C5 N1 1.4200 . ?
C5 C5 1.42(6) 8_545 ?
C5 C5 1.84(5) 2_655 ?
C5 C3 1.857(2) 8_545 ?
C5 N2 1.82(3) 8_545 ?
C5 H5A 0.9595 . ?
N1 N1 0.46(8) 8_545 ?
N1 C5 0.58(5) 2_655 ?
N1 N1 0.88(6) 7 ?
N1 C5 0.994(9) 7 ?
N1 C5 1.17(2) 8_545 ?
N1 N1 0.99(5) 2_655 ?
N1 C4 1.4200 . ?
N1 N2 1.73(3) 2_655 ?
N1 C4 1.75(3) 7 ?
N1 N2 1.85(3) 7 ?
N1 C4 1.73(4) 8_545 ?
N1 H1A 0.9025 . ?
C4 N2 0.90(4) 2_655 ?
C4 C5 0.92(3) 2_655 ?
C4 C3 1.105(16) 7 ?
C4 C4 1.19(6) 7 ?
C4 C5 1.498(14) 8_545 ?
C4 C3 1.4200 . ?
C4 N2 1.66(3) 7 ?
C4 N2 1.83(3) 8_545 ?
C4 N1 1.75(3) 7 ?
C4 N1 1.73(6) 8_545 ?
C4 C3 1.99(5) 2_655 ?
C4 H4A 0.9563 . ?
C3 C3 0.67(7) 7 ?
C3 N2 0.92(2) 8_545 ?
C3 C4 1.105(13) 7 ?
C3 C3 1.29(5) 8_545 ?
C3 N2 1.51(6) 2_655 ?
C3 C3 1.45(6) 2_655 ?
C3 C5 1.857(2) 8_545 ?
C3 N2 1.85(5) 7 ?
C3 C5 2.06(2) 2_655 ?
C3 C4 1.99(3) 2_655 ?
C3 H3A 0.9635 . ?

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 178.3(7) 3_566 4_656 ?
O1 Mn1 O1 90.013(11) 3_566 . ?
O1 Mn1 O1 90.013(12) 4_656 . ?
O1 Mn1 O1 90.013(12) 3_566 2_665 ?
O1 Mn1 O1 90.013(12) 4_656 2_665 ?
O1 Mn1 O1 178.3(7) . 2_665 ?
O1 Mn1 O2 95.4(14) 3_566 4_656 ?
O1 Mn1 O2 83.0(13) 4_656 4_656 ?
O1 Mn1 O2 97.1(10) . 4_656 ?
O1 Mn1 O2 84.6(10) 2_665 4_656 ?
O1 Mn1 O2 97.1(10) 3_566 . ?
O1 Mn1 O2 84.6(10) 4_656 . ?
O1 Mn1 O2 83.0(13) . . ?
O1 Mn1 O2 95.4(14) 2_665 . ?
O2 Mn1 O2 167.6(6) 4_656 . ?
O1 Mn1 O2 83.0(13) 3_566 3_566 ?
O1 Mn1 O2 95.4(14) 4_656 3_566 ?
O1 Mn1 O2 84.6(10) . 3_566 ?
O1 Mn1 O2 97.1(10) 2_665 3_566 ?
O2 Mn1 O2 17.6(9) 4_656 3_566 ?
O2 Mn1 O2 167.6(6) . 3_566 ?
O1 Mn1 O2 84.6(10) 3_566 2_665 ?
O1 Mn1 O2 97.1(10) 4_656 2_665 ?
O1 Mn1 O2 95.4(14) . 2_665 ?
O1 Mn1 O2 83.0(13) 2_665 2_665 ?
O2 Mn1 O2 167.6(6) 4_656 2_665 ?
O2 Mn1 O2 17.6(9) . 2_665 ?
O2 Mn1 O2 167.6(6) 3_566 2_665 ?
O1 Mn1 Mn1 159.51(16) 3_566 5_656 ?
O1 Mn1 Mn1 20.49(16) 4_656 5_656 ?
O1 Mn1 Mn1 110.47(17) . 5_656 ?
O1 Mn1 Mn1 69.53(17) 2_665 5_656 ?
O2 Mn1 Mn1 82.0(9) 4_656 5_656 ?
O2 Mn1 Mn1 86.3(13) . 5_656 ?
O2 Mn1 Mn1 98.0(9) 3_566 5_656 ?
O2 Mn1 Mn1 93.7(13) 2_665 5_656 ?
O1 Mn1 Mn1 20.49(16) 3_566 5_546 ?
O1 Mn1 Mn1 159.51(16) 4_656 5_546 ?
O1 Mn1 Mn1 69.53(17) . 5_546 ?
O1 Mn1 Mn1 110.47(17) 2_665 5_546 ?
O2 Mn1 Mn1 98.0(9) 4_656 5_546 ?
O2 Mn1 Mn1 93.7(13) . 5_546 ?
O2 Mn1 Mn1 82.0(9) 3_566 5_546 ?
O2 Mn1 Mn1 86.3(13) 2_665 5_546 ?
Mn1 Mn1 Mn1 180.0 5_656 5_546 ?
O1 Mn1 Mn1 110.47(17) 3_566 5_646 ?
O1 Mn1 Mn1 69.53(17) 4_656 5_646 ?
O1 Mn1 Mn1 20.49(16) . 5_646 ?
O1 Mn1 Mn1 159.51(16) 2_665 5_646 ?
O2 Mn1 Mn1 93.7(13) 4_656 5_646 ?
O2 Mn1 Mn1 82.0(9) . 5_646 ?
O2 Mn1 Mn1 86.3(13) 3_566 5_646 ?
O2 Mn1 Mn1 98.0(9) 2_665 5_646 ?
Mn1 Mn1 Mn1 90.0 5_656 5_646 ?
Mn1 Mn1 Mn1 90.0 5_546 5_646 ?
O1 Mn1 Mn1 69.53(17) 3_566 5_556 ?
O1 Mn1 Mn1 110.47(17) 4_656 5_556 ?
O1 Mn1 Mn1 159.51(16) . 5_556 ?
O1 Mn1 Mn1 20.49(16) 2_665 5_556 ?
O2 Mn1 Mn1 86.3(13) 4_656 5_556 ?
O2 Mn1 Mn1 98.0(9) . 5_556 ?
O2 Mn1 Mn1 93.7(13) 3_566 5_556 ?
O2 Mn1 Mn1 82.0(9) 2_665 5_556 ?
Mn1 Mn1 Mn1 90.0 5_656 5_556 ?
Mn1 Mn1 Mn1 90.0 5_546 5_556 ?
Mn1 Mn1 Mn1 180.0 5_646 5_556 ?
O1 C1 O1 138.8(17) 8_545 . ?
O1 C1 H1 110.5 8_545 . ?
O1 C1 H1 110.6 . . ?
C1 O1 Mn1 139.1(10) . . ?
O2 C2 O2 155.3(12) 3_567 2_665 ?
O2 C2 O2 35.2(18) 3_567 4_657 ?
O2 C2 O2 155.3(12) 2_665 4_657 ?
O2 C2 O2 155.3(12) 3_567 . ?
O2 C2 O2 35.2(18) 2_665 . ?
O2 C2 O2 155.3(12) 4_657 . ?
O2 C2 H2 99.7 3_567 . ?
O2 C2 H2 75.4 2_665 . ?
O2 C2 H2 80.3 4_657 . ?
O2 C2 H2 104.6 . . ?
O2 O2 C2 72.4(9) 2_665 . ?
O2 O2 Mn1 81.2(4) 2_665 . ?
C2 O2 Mn1 153.6(13) . . ?
O2 O2 H2 46.3 2_665 . ?
C2 O2 H2 34.4 . . ?
Mn1 O2 H2 122.2 . . ?
C3 N2 C4 75(4) 8_545 2_655 ?
C3 N2 N2 102(3) 8_545 8_545 ?
C4 N2 N2 133(2) 2_655 8_545 ?
C3 N2 C5 103.1(8) 8_545 . ?
C4 N2 C5 39.4(15) 2_655 . ?
N2 N2 C5 100.4(14) 8_545 . ?
C3 N2 C3 62(3) 8_545 . ?
C4 N2 C3 117(3) 2_655 . ?
N2 N2 C3 39.3(12) 8_545 . ?
C5 N2 C3 108.0 . . ?
C3 N2 C3 15.7(13) 8_545 2_655 ?
C4 N2 C3 67(3) 2_655 2_655 ?
N2 N2 C3 97.1(16) 8_545 2_655 ?
C5 N2 C3 89.3(10) . 2_655 ?
C3 N2 C3 59(2) . 2_655 ?
C3 N2 N1 106(2) 8_545 2_655 ?
C4 N2 N1 55(2) 2_655 2_655 ?
N2 N2 N1 82.5(14) 8_545 2_655 ?
C5 N2 N1 18(2) . 2_655 ?
C3 N2 N1 93.2(17) . 2_655 ?
C3 N2 N1 90(2) 2_655 2_655 ?
C3 N2 C4 97(3) 8_545 7 ?
C4 N2 C4 110(3) 2_655 7 ?
N2 N2 C4 23.3(13) 8_545 7 ?
C5 N2 C4 79.2(6) . 7 ?
C3 N2 C4 41.2(9) . 7 ?
C3 N2 C4 87(3) 2_655 7 ?
N1 N2 C4 61(2) 2_655 7 ?
C3 N2 C4 49.9(9) 8_545 8_545 ?
C4 N2 C4 34(3) 2_655 8_545 ?
N2 N2 C4 109.5(10) 8_545 8_545 ?
C5 N2 C4 53.2 . 8_545 ?
C3 N2 C4 83.5(13) . 8_545 ?
C3 N2 C4 37.2(11) 2_655 8_545 ?
N1 N2 C4 59(2) 2_655 8_545 ?
C4 N2 C4 88.8(15) 7 8_545 ?
C3 N2 N1 108(2) 8_545 7 ?
C4 N2 N1 68.4(16) 2_655 7 ?
N2 N2 N1 68.2(13) 8_545 7 ?
C5 N2 N1 32.19(17) . 7 ?
C3 N2 N1 81.9(9) . 7 ?
C3 N2 N1 92(2) 2_655 7 ?
N1 N2 N1 14(2) 2_655 7 ?
C4 N2 N1 47.4(5) 7 7 ?
C4 N2 N1 66.4(17) 8_545 7 ?
C3 N2 C5 110(2) 8_545 8_545 ?
C4 N2 C5 85.9(13) 2_655 8_545 ?
N2 N2 C5 50.1(11) 8_545 8_545 ?
C5 N2 C5 50.3(14) . 8_545 ?
C3 N2 C5 68.6(11) . 8_545 ?
C3 N2 C5 95.0(17) 2_655 8_545 ?
N1 N2 C5 32.4(10) 2_655 8_545 ?
C4 N2 C5 30.3(13) 7 8_545 ?
C4 N2 C5 78.1(11) 8_545 8_545 ?
N1 N2 C5 18.1(13) 7 8_545 ?
C3 N2 C3 50(3) 8_545 7 ?
C4 N2 C3 99(4) 2_655 7 ?
N2 N2 C3 53.7(13) 8_545 7 ?
C5 N2 C3 96.6(9) . 7 ?
C3 N2 C3 18.0(14) . 7 ?
C3 N2 C3 43(2) 2_655 7 ?
N1 N2 C3 85.0(17) 2_655 7 ?
C4 N2 C3 47.3(11) 7 7 ?
C4 N2 C3 65.5(15) 8_545 7 ?
N1 N2 C3 76.7(13) 7 7 ?
C5 N2 C3 68.1(7) 8_545 7 ?
C3 N2 H2A 95.8 8_545 . ?
C4 N2 H2A 101.1 2_655 . ?
N2 N2 H2A 125.9 8_545 . ?
C5 N2 H2A 124.8 . . ?
C3 N2 H2A 126.6 . . ?
C3 N2 H2A 110.2 2_655 . ?
N1 N2 H2A 140.2 2_655 . ?
C4 N2 H2A 149.0 7 . ?
C4 N2 H2A 120.7 8_545 . ?
N1 N2 H2A 149.9 7 . ?
C5 N2 H2A 154.6 8_545 . ?
C3 N2 H2A 133.4 7 . ?
N1 C5 C5 75(7) 2_655 7 ?
N1 C5 C4 141(4) 2_655 2_655 ?
C5 C5 C4 91(4) 7 2_655 ?
N1 C5 N1 15(4) 2_655 7 ?
C5 C5 N1 82(3) 7 7 ?
C4 C5 N1 129.0(19) 2_655 7 ?
N1 C5 N1 47(6) 2_655 8_545 ?
C5 C5 N1 29(3) 7 8_545 ?
C4 C5 N1 113(4) 2_655 8_545 ?
N1 C5 N1 54(4) 7 8_545 ?
N1 C5 C4 106(6) 2_655 8_545 ?
C5 C5 C4 38.0(6) 7 8_545 ?
C4 C5 C4 53(4) 2_655 8_545 ?
N1 C5 C4 106(3) 7 8_545 ?
N1 C5 C4 63.0(13) 8_545 8_545 ?
N1 C5 N1 34(6) 2_655 . ?
C5 C5 N1 43.8 7 . ?
C4 C5 N1 117(3) 2_655 . ?
N1 C5 N1 38(3) 7 . ?
N1 C5 N1 17(3) 8_545 . ?
C4 C5 N1 72.7(15) 8_545 . ?
N1 C5 N2 113(5) 2_655 . ?
C5 C5 N2 109.7 7 . ?
C4 C5 N2 38(3) 2_655 . ?
N1 C5 N2 98.3(11) 7 . ?
N1 C5 N2 116.5(15) 8_545 . ?
C4 C5 N2 77.4(5) 8_545 . ?
N1 C5 N2 108.0 . . ?
N1 C5 C5 34(5) 2_655 8_545 ?
C5 C5 C5 90.0 7 8_545 ?
C4 C5 C5 113(2) 2_655 8_545 ?
N1 C5 C5 18.8(15) 7 8_545 ?
N1 C5 C5 66(3) 8_545 8_545 ?
C4 C5 C5 103.7(18) 8_545 8_545 ?
N1 C5 C5 48.5 . 8_545 ?
N2 C5 C5 79.6 . 8_545 ?
N1 C5 C5 37(4) 2_655 2_655 ?
C5 C5 C5 51(2) 7 2_655 ?
C4 C5 C5 108(3) 2_655 2_655 ?
N1 C5 C5 34(2) 7 2_655 ?
N1 C5 C5 28.8(18) 8_545 2_655 ?
C4 C5 C5 71.5(14) 8_545 2_655 ?
N1 C5 C5 14.0(13) . 2_655 ?
N2 C5 C5 94.3(9) . 2_655 ?
C5 C5 C5 39(2) 8_545 2_655 ?
N1 C5 C3 115(3) 2_655 8_545 ?
C5 C5 C3 82.2 7 8_545 ?
C4 C5 C3 26.0(19) 2_655 8_545 ?
N1 C5 C3 103.2(19) 7 8_545 ?
N1 C5 C3 96.2(7) 8_545 8_545 ?
C4 C5 C3 48.6(6) 8_545 8_545 ?
N1 C5 C3 94.4(11) . 8_545 ?
N2 C5 C3 28.8(5) . 8_545 ?
C5 C5 C3 87.9(17) 8_545 8_545 ?
C5 C5 C3 83.4(14) 2_655 8_545 ?
N1 C5 N2 83(5) 2_655 8_545 ?
C5 C5 N2 105.2(7) 7 8_545 ?
C4 C5 N2 65(2) 2_655 8_545 ?
N1 C5 N2 68.7(17) 7 8_545 ?
N1 C5 N2 98(2) 8_545 8_545 ?
C4 C5 N2 87.1(11) 8_545 8_545 ?
N1 C5 N2 84.8(13) . 8_545 ?
N2 C5 N2 29.5(14) . 8_545 ?
C5 C5 N2 50.1(14) 8_545 8_545 ?
C5 C5 N2 70.8(14) 2_655 8_545 ?
C3 C5 N2 45.4(5) 8_545 8_545 ?
N1 C5 H5A 112.0 2_655 . ?
C5 C5 H5A 108.9 7 . ?
C4 C5 H5A 107.0 2_655 . ?
N1 C5 H5A 123.2 7 . ?
N1 C5 H5A 115.5 8_545 . ?
C4 C5 H5A 116.0 8_545 . ?
N1 C5 H5A 125.8 . . ?
N2 C5 H5A 126.2 . . ?
C5 C5 H5A 135.7 8_545 . ?
C5 C5 H5A 139.4 2_655 . ?
C3 C5 H5A 133.1 8_545 . ?
N2 C5 H5A 145.0 8_545 . ?
N1 N1 C5 146(5) 8_545 2_655 ?
N1 N1 N1 90.0 8_545 7 ?
C5 N1 N1 105(6) 2_655 7 ?
N1 N1 C5 18.8(16) 8_545 7 ?
C5 N1 C5 128(6) 2_655 7 ?
N1 N1 C5 98(4) 7 7 ?
N1 N1 C5 114(3) 8_545 8_545 ?
C5 N1 C5 76(7) 2_655 8_545 ?
N1 N1 C5 29(2) 7 8_545 ?
C5 N1 C5 117(3) 7 8_545 ?
N1 N1 N1 62(4) 8_545 2_655 ?
C5 N1 N1 127(8) 2_655 2_655 ?
N1 N1 N1 28(4) 7 2_655 ?
C5 N1 N1 72(3) 7 2_655 ?
C5 N1 N1 54(2) 8_545 2_655 ?
N1 N1 C5 48.5 8_545 . ?
C5 N1 C5 129(4) 2_655 . ?
N1 N1 C5 43.8 7 . ?
C5 N1 C5 55(4) 7 . ?
C5 N1 C5 66(3) 8_545 . ?
N1 N1 C5 19(3) 2_655 . ?
N1 N1 C4 126.1 8_545 . ?
C5 N1 C4 24(2) 2_655 . ?
N1 N1 C4 96.3 7 . ?
C5 N1 C4 108.2(6) 7 . ?
C5 N1 C4 69.9(13) 8_545 . ?
N1 N1 C4 112(2) 2_655 . ?
C5 N1 C4 108.0 . . ?
N1 N1 N2 97.5(13) 8_545 2_655 ?
C5 N1 N2 49(4) 2_655 2_655 ?
N1 N1 N2 111.2(19) 7 2_655 ?
C5 N1 N2 78.9(17) 7 2_655 ?
C5 N1 N2 92.1(19) 8_545 2_655 ?
N1 N1 N2 112.4(17) 2_655 2_655 ?
C5 N1 N2 99.3(15) . 2_655 ?
C4 N1 N2 31.2(15) . 2_655 ?
N1 N1 C4 118.6(6) 8_545 7 ?
C5 N1 C4 55(4) 2_655 7 ?
N1 N1 C4 53.8(15) 7 7 ?
C5 N1 C4 111(2) 7 7 ?
C5 N1 C4 29.0(16) 8_545 7 ?
N1 N1 C4 72(4) 2_655 7 ?
C5 N1 C4 76.1(11) . 7 ?
C4 N1 C4 42.5(15) . 7 ?
N2 N1 C4 63.3(14) 2_655 7 ?
N1 N1 N2 68.2(14) 8_545 7 ?
C5 N1 N2 78(4) 2_655 7 ?
N1 N1 N2 109.8(19) 7 7 ?
C5 N1 N2 49.6(9) 7 7 ?
C5 N1 N2 103.8(19) 8_545 7 ?
N1 N1 N2 97(3) 2_655 7 ?
C5 N1 N2 79.9(19) . 7 ?
C4 N1 N2 59.3(13) . 7 ?
N2 N1 N2 29.3(16) 2_655 7 ?
C4 N1 N2 79.4(11) 7 7 ?
N1 N1 C4 41.5(11) 8_545 8_545 ?
C5 N1 C4 106(3) 2_655 8_545 ?
N1 N1 C4 95.13(11) 7 8_545 ?
C5 N1 C4 24.5(12) 7 8_545 ?
C5 N1 C4 103.2(18) 8_545 8_545 ?
N1 N1 C4 75(3) 2_655 8_545 ?
C5 N1 C4 55.7(5) . 8_545 ?
C4 N1 C4 84.6(11) . 8_545 ?
N2 N1 C4 57.3(9) 2_655 8_545 ?
C4 N1 C4 89.1(7) 7 8_545 ?
N2 N1 C4 28.8(12) 7 8_545 ?
N1 N1 H1A 93.4 8_545 . ?
C5 N1 H1A 103.8 2_655 . ?
N1 N1 H1A 121.3 7 . ?
C5 N1 H1A 103.0 7 . ?
C5 N1 H1A 129.7 8_545 . ?
N1 N1 H1A 119.2 2_655 . ?
C5 N1 H1A 125.8 . . ?
C4 N1 H1A 126.2 . . ?
N2 N1 H1A 126.3 2_655 . ?
C4 N1 H1A 146.3 7 . ?
N2 N1 H1A 125.7 7 . ?
C4 N1 H1A 123.9 8_545 . ?
N2 C4 C5 103(6) 2_655 2_655 ?
N2 C4 C3 53.4(15) 2_655 7 ?
C5 C4 C3 132(3) 2_655 7 ?
N2 C4 C4 122(3) 2_655 7 ?
C5 C4 C4 89(3) 2_655 7 ?
C3 C4 C4 76(3) 7 7 ?
N2 C4 C5 123(3) 2_655 8_545 ?
C5 C4 C5 51(3) 2_655 8_545 ?
C3 C4 C5 103(3) 7 8_545 ?
C4 C4 C5 38.0(7) 7 8_545 ?
N2 C4 C3 77(4) 2_655 . ?
C5 C4 C3 121(3) 2_655 . ?
C3 C4 C3 27(3) 7 . ?
C4 C4 C3 49.1 7 . ?
C5 C4 C3 79.0(6) 8_545 . ?
N2 C4 N1 94(2) 2_655 . ?
C5 C4 N1 15(3) 2_655 . ?
C3 C4 N1 117.6(8) 7 . ?
C4 C4 N1 83.7 7 . ?
C5 C4 N1 47.1(13) 8_545 . ?
C3 C4 N1 108.0 . . ?
N2 C4 N2 23.8(16) 2_655 7 ?
C5 C4 N2 85(4) 2_655 7 ?
C3 C4 N2 57.8(9) 7 7 ?
C4 C4 N2 106(2) 7 7 ?
C5 C4 N2 99(2) 8_545 7 ?
C3 C4 N2 74(2) . 7 ?
N1 C4 N2 73.2(14) . 7 ?
N2 C4 N2 97(4) 2_655 8_545 ?
C5 C4 N2 95(3) 2_655 8_545 ?
C3 C4 N2 55(3) 7 8_545 ?
C4 C4 N2 24.7(12) 7 8_545 ?
C5 C4 N2 49.4(11) 8_545 8_545 ?
C3 C4 N2 29.7(7) . 8_545 ?
N1 C4 N2 84.6(8) . 8_545 ?
N2 C4 N2 83(2) 7 8_545 ?
N2 C4 N1 108.5(18) 2_655 7 ?
C5 C4 N1 37.9(17) 2_655 7 ?
C3 C4 N1 105(2) 7 7 ?
C4 C4 N1 53.8(16) 7 7 ?
C5 C4 N1 18.5(18) 8_545 7 ?
C3 C4 N1 85.5(12) . 7 ?
N1 C4 N1 30.0(16) . 7 ?
N2 C4 N1 84.7(12) 7 7 ?
N2 C4 N1 57.8(13) 8_545 7 ?
N2 C4 N1 83(3) 2_655 8_545 ?
C5 C4 N1 27(2) 2_655 8_545 ?
C3 C4 N1 106.2(16) 7 8_545 ?
C4 C4 N1 84.87(17) 7 8_545 ?
C5 C4 N1 51.6(12) 8_545 8_545 ?
C3 C4 N1 100.0(11) . 8_545 ?
N1 C4 N1 12.4(17) . 8_545 ?
N2 C4 N1 61(2) 7 8_545 ?
N2 C4 N1 80.5(12) 8_545 8_545 ?
N1 C4 N1 33.1(14) 7 8_545 ?
N2 C4 C3 39.6(17) 2_655 2_655 ?
C5 C4 C3 97(4) 2_655 2_655 ?
C3 C4 C3 36.6(8) 7 2_655 ?
C4 C4 C3 83(2) 7 2_655 ?
C5 C4 C3 89(2) 8_545 2_655 ?
C3 C4 C3 46.7(17) . 2_655 ?
N1 C4 C3 82.9(8) . 2_655 ?
N2 C4 C3 27.3(6) 7 2_655 ?
N2 C4 C3 58.0(18) 8_545 2_655 ?
N1 C4 C3 80.5(13) 7 2_655 ?
N1 C4 C3 70.8(17) 8_545 2_655 ?
N2 C4 H4A 97.4 2_655 . ?
C5 C4 H4A 112.3 2_655 . ?
C3 C4 H4A 111.2 7 . ?
C4 C4 H4A 130.5 7 . ?
C5 C4 H4A 137.8 8_545 . ?
C3 C4 H4A 126.0 . . ?
N1 C4 H4A 126.0 . . ?
N2 C4 H4A 119.0 7 . ?
N2 C4 H4A 145.0 8_545 . ?
N1 C4 H4A 143.5 7 . ?
N1 C4 H4A 133.1 8_545 . ?
C3 C4 H4A 133.5 2_655 . ?
C3 C3 N2 142.5(9) 7 8_545 ?
C3 C3 C4 104(3) 7 7 ?
N2 C3 C4 52(3) 8_545 7 ?
C3 C3 C3 90.0 7 8_545 ?
N2 C3 C3 78(3) 8_545 8_545 ?
C4 C3 C3 112.6(3) 7 8_545 ?
C3 C3 C4 49.1 7 . ?
N2 C3 C4 100.4(19) 8_545 . ?
C4 C3 C4 54(3) 7 . ?
C3 C3 C4 107.4 8_545 . ?
C3 C3 N2 120.9 7 . ?
N2 C3 N2 39(3) 8_545 . ?
C4 C3 N2 81.1(14) 7 . ?
C3 C3 N2 39.3 8_545 . ?
C4 C3 N2 108.0 . . ?
C3 C3 N2 21.8(12) 7 2_655 ?
N2 C3 N2 120.8(17) 8_545 2_655 ?
C4 C3 N2 87(3) 7 2_655 ?
C3 C3 N2 82.9(15) 8_545 2_655 ?
C4 C3 N2 35.5(14) . 2_655 ?
N2 C3 N2 104.5(13) . 2_655 ?
C3 C3 C3 62(3) 7 2_655 ?
N2 C3 C3 101(3) 8_545 2_655 ?
C4 C3 C3 116.7(12) 7 2_655 ?
C3 C3 C3 28(3) 8_545 2_655 ?
C4 C3 C3 87.9(19) . 2_655 ?
N2 C3 C3 63(2) . 2_655 ?
N2 C3 C3 57(2) 2_655 2_655 ?
C3 C3 C5 97.8 7 8_545 ?
N2 C3 C5 48(2) 8_545 8_545 ?
C4 C3 C5 21.5(18) 7 8_545 ?
C3 C3 C5 92.1(18) 8_545 8_545 ?
C4 C3 C5 52.3(6) . 8_545 ?
N2 C3 C5 65.9(15) . 8_545 ?
N2 C3 C5 77.5(13) 2_655 8_545 ?
C3 C3 C5 95.5(16) 2_655 8_545 ?
C3 C3 N2 41.1(16) 7 7 ?
N2 C3 N2 108.4(17) 8_545 7 ?
C4 C3 N2 99(2) 7 7 ?
C3 C3 N2 53.7(18) 8_545 7 ?
C4 C3 N2 59.1(16) . 7 ?
N2 C3 N2 79.8(16) . 7 ?
N2 C3 N2 29(2) 2_655 7 ?
C3 C3 N2 29.1(10) 2_655 7 ?
C5 C3 N2 80.9(13) 8_545 7 ?
C3 C3 C5 63.4(14) 7 2_655 ?
N2 C3 C5 81.3(17) 8_545 2_655 ?
C4 C3 C5 45.1(17) 7 2_655 ?
C3 C3 C5 91.9(19) 8_545 2_655 ?
C4 C3 C5 22.5(12) . 2_655 ?
N2 C3 C5 85.6(13) . 2_655 ?
N2 C3 C5 43.6(15) 2_655 2_655 ?
C3 C3 C5 80(2) 2_655 2_655 ?
C5 C3 C5 34.3(14) 8_545 2_655 ?
N2 C3 C5 55.2(17) 7 2_655 ?
C3 C3 C4 97.5(19) 7 2_655 ?
N2 C3 C4 55.8(19) 8_545 2_655 ?
C4 C3 C4 81.7(8) 7 2_655 ?
C3 C3 C4 30.8(8) 8_545 2_655 ?
C4 C3 C4 89.8(12) . 2_655 ?
N2 C3 C4 23.7(19) . 2_655 ?
N2 C3 C4 80.9(18) 2_655 2_655 ?
C3 C3 C4 45.5(12) 2_655 2_655 ?
C5 C3 C4 61.5(14) 8_545 2_655 ?
N2 C3 C4 56.6(5) 7 2_655 ?
C5 C3 C4 69.1(13) 2_655 2_655 ?
C3 C3 H3A 97.0 7 . ?
N2 C3 H3A 120.4 8_545 . ?
C4 C3 H3A 128.8 7 . ?
C3 C3 H3A 113.8 8_545 . ?
C4 C3 H3A 126.1 . . ?
N2 C3 H3A 125.9 . . ?
N2 C3 H3A 118.7 2_655 . ?
C3 C3 H3A 114.4 2_655 . ?
C5 C3 H3A 150.1 8_545 . ?
N2 C3 H3A 126.0 7 . ?
C5 C3 H3A 148.4 2_655 . ?
C4 C3 H3A 141.3 2_655 . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         1.022
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.160
