# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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 1515781'
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2017-01-10 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         'C6 Mn N9,C9 H20 P'
_chemical_formula_sum            'C15 H20 Mn N9 P'
_chemical_formula_weight         412.31

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'
P P 0.1023 0.0942 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.098(2)
_cell_length_b                   12.156(2)
_cell_length_c                   17.119(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.32(3)
_cell_angle_gamma                90
_cell_volume                     2088.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3275
_cell_measurement_theta_min      1.7642
_cell_measurement_theta_max      27.1643

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             852
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.726
_shelx_estimated_absorpt_T_min   0.868
_shelx_estimated_absorpt_T_max   0.868
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14170
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.305
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             4636
_reflns_number_gt                3786
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0629P)²+1.2616P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4636
_refine_ls_number_parameters     238
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1319
_refine_ls_wR_factor_gt          0.1234
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001

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 0.73110(4) 0.77455(3) 0.21230(2) 0.04211(14) Uani 1 1 d . . . . .
P1 P 0.77281(8) 0.25280(6) -0.01044(4) 0.0530(2) Uani 1 1 d . . . . .
C12 C 0.6526(3) 1.0373(2) 0.19286(16) 0.0528(6) Uani 1 1 d . . . . .
C10 C 0.8226(3) 0.5131(2) 0.25089(18) 0.0561(7) Uani 1 1 d . . . . .
C11 C 0.9625(3) 0.3696(2) 0.27910(17) 0.0537(6) Uani 1 1 d . . . . .
C14 C 0.7586(3) 0.8386(2) 0.40331(16) 0.0589(7) Uani 1 1 d . . . . .
N4 N 0.6736(3) 0.9464(2) 0.18471(18) 0.0714(7) Uani 1 1 d . . . . .
N1 N 0.7915(3) 0.6019(2) 0.23928(16) 0.0688(7) Uani 1 1 d . . . . .
C13 C 0.5500(3) 1.1858(2) 0.23658(18) 0.0565(7) Uani 1 1 d . . . . .
N5 N 0.6373(3) 1.1433(2) 0.19520(18) 0.0736(8) Uani 1 1 d . . . . .
N2 N 0.8434(3) 0.4091(2) 0.2642(2) 0.0831(9) Uani 1 1 d . . . . .
C1 C 0.6361(3) 0.1560(3) -0.01882(19) 0.0622(7) Uani 1 1 d . . . . .
H1A H 0.6281 0.1247 0.0326 0.075 Uiso 1 1 calc R U . . .
H1B H 0.5542 0.1953 -0.0353 0.075 Uiso 1 1 calc R U . . .
N7 N 0.7571(4) 0.8161(3) 0.33947(16) 0.0843(9) Uani 1 1 d . . . . .
C4 C 0.9306(3) 0.1783(3) 0.0089(2) 0.0774(9) Uani 1 1 d . . . . .
H4A H 0.9387 0.1280 -0.0343 0.093 Uiso 1 1 calc R U . . .
H4B H 1.0031 0.2307 0.0100 0.093 Uiso 1 1 calc R U . . .
C8 C 0.7778(4) 0.3246(3) -0.10198(19) 0.0732(9) Uani 1 1 d . . . . .
H8A H 0.7716 0.2707 -0.1440 0.088 Uiso 1 1 calc R U . . .
H8B H 0.6995 0.3711 -0.1104 0.088 Uiso 1 1 calc R U . . .
C2 C 0.6513(4) 0.0659(3) -0.0748(2) 0.0732(9) Uani 1 1 d D . . . .
H2 H 0.6450 0.0828 -0.1281 0.088 Uiso 1 1 calc R U . . .
C9 C 0.8979(4) 0.3943(3) -0.1087(2) 0.0798(10) Uani 1 1 d . . . . .
H9A H 0.9167 0.4374 -0.0618 0.120 Uiso 1 1 calc R U . . .
H9B H 0.8813 0.4423 -0.1532 0.120 Uiso 1 1 calc R U . . .
H9C H 0.9728 0.3479 -0.1153 0.120 Uiso 1 1 calc R U . . .
C6 C 0.7590(4) 0.3465(3) 0.0678(2) 0.0788(10) Uani 1 1 d . . . . .
H6A H 0.7825 0.3088 0.1173 0.095 Uiso 1 1 calc R U . . .
H6B H 0.8224 0.4058 0.0644 0.095 Uiso 1 1 calc R U . . .
N8 N 0.7670(4) 0.8757(3) 0.47431(16) 0.0965(12) Uani 1 1 d . . . . .
C5 C 0.9456(4) 0.1148(4) 0.0835(2) 0.0928(12) Uani 1 1 d . . . . .
H5A H 0.9314 0.1627 0.1264 0.139 Uiso 1 1 calc R U . . .
H5B H 1.0338 0.0844 0.0919 0.139 Uiso 1 1 calc R U . . .
H5C H 0.8814 0.0563 0.0805 0.139 Uiso 1 1 calc R U . . .
C3 C 0.6731(4) -0.0369(3) -0.0537(3) 0.0929(12) Uani 1 1 d D . . . .
H3A H 0.6798 -0.0561 -0.0008 0.111 Uiso 1 1 calc R U . . .
H3B H 0.6818 -0.0904 -0.0916 0.111 Uiso 1 1 calc R U . . .
C7 C 0.6180(5) 0.3960(4) 0.0675(3) 0.1020(14) Uani 1 1 d . . . . .
H7A H 0.5898 0.4263 0.0166 0.153 Uiso 1 1 calc R U . . .
H7B H 0.6196 0.4531 0.1064 0.153 Uiso 1 1 calc R U . . .
H7C H 0.5569 0.3395 0.0793 0.153 Uiso 1 1 calc R U . . .
N3 N 1.0592(3) 0.3241(2) 0.2939(2) 0.0834(9) Uani 1 1 d . . . . .
N6 N 0.4786(3) 1.2311(2) 0.2726(2) 0.0768(8) Uani 1 1 d . . . . .
C15 C 0.7318(3) 0.8166(2) 0.53167(16) 0.0577(7) Uani 1 1 d . . . . .
N9 N 0.7053(3) 0.7747(2) 0.58670(15) 0.0734(8) 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 N4 2.205(3) . ?
Mn1 N3 2.215(3) 2_755 ?
Mn1 N9 2.220(3) 4_575 ?
Mn1 N1 2.220(3) . ?
Mn1 N7 2.222(3) . ?
Mn1 N6 2.225(3) 2_645 ?
P1 C6 1.776(4) . ?
P1 C8 1.799(3) . ?
P1 C1 1.807(3) . ?
P1 C4 1.831(3) . ?
C12 N4 1.137(4) . ?
C12 N5 1.299(4) . ?
C10 N1 1.135(4) . ?
C10 N2 1.298(4) . ?
C11 N3 1.128(4) . ?
C11 N2 1.294(4) . ?
C14 N7 1.125(4) . ?
C14 N8 1.290(4) . ?
C13 N6 1.140(4) . ?
C13 N5 1.298(4) . ?
C1 C2 1.475(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C4 C5 1.485(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C8 C9 1.494(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C2 C3 1.312(5) . ?
C2 H2 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C6 C7 1.546(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
N8 C15 1.297(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C3 H3A 0.9300 . ?
C3 H3B 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
N3 Mn1 2.215(3) 2_745 ?
N6 Mn1 2.225(3) 2_655 ?
C15 N9 1.129(4) . ?
N9 Mn1 2.220(3) 4_576 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Mn1 N3 87.85(11) . 2_755 ?
N4 Mn1 N9 92.75(11) . 4_575 ?
N3 Mn1 N9 92.16(13) 2_755 4_575 ?
N4 Mn1 N1 179.21(11) . . ?
N3 Mn1 N1 91.43(11) 2_755 . ?
N9 Mn1 N1 86.94(10) 4_575 . ?
N4 Mn1 N7 89.67(12) . . ?
N3 Mn1 N7 88.57(13) 2_755 . ?
N9 Mn1 N7 177.49(11) 4_575 . ?
N1 Mn1 N7 90.64(11) . . ?
N4 Mn1 N6 91.06(11) . 2_645 ?
N3 Mn1 N6 175.66(12) 2_755 2_645 ?
N9 Mn1 N6 92.09(13) 4_575 2_645 ?
N1 Mn1 N6 89.68(11) . 2_645 ?
N7 Mn1 N6 87.22(13) . 2_645 ?
C6 P1 C8 110.98(18) . . ?
C6 P1 C1 110.78(17) . . ?
C8 P1 C1 109.92(16) . . ?
C6 P1 C4 108.65(18) . . ?
C8 P1 C4 106.90(17) . . ?
C1 P1 C4 109.52(16) . . ?
N4 C12 N5 173.0(3) . . ?
N1 C10 N2 173.3(4) . . ?
N3 C11 N2 172.0(3) . . ?
N7 C14 N8 172.9(4) . . ?
C12 N4 Mn1 160.5(3) . . ?
C10 N1 Mn1 178.1(3) . . ?
N6 C13 N5 174.5(3) . . ?
C12 N5 C13 120.2(3) . . ?
C11 N2 C10 121.7(3) . . ?
C2 C1 P1 113.7(2) . . ?
C2 C1 H1A 108.8 . . ?
P1 C1 H1A 108.8 . . ?
C2 C1 H1B 108.8 . . ?
P1 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
C14 N7 Mn1 174.0(3) . . ?
C5 C4 P1 114.7(3) . . ?
C5 C4 H4A 108.6 . . ?
P1 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
P1 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C9 C8 P1 116.3(3) . . ?
C9 C8 H8A 108.2 . . ?
P1 C8 H8A 108.2 . . ?
C9 C8 H8B 108.2 . . ?
P1 C8 H8B 108.2 . . ?
H8A C8 H8B 107.4 . . ?
C3 C2 C1 123.7(4) . . ?
C3 C2 H2 118.2 . . ?
C1 C2 H2 118.2 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C6 P1 113.3(3) . . ?
C7 C6 H6A 108.9 . . ?
P1 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
P1 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C15 N8 C14 121.6(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C2 C3 H3A 120.0 . . ?
C2 C3 H3B 120.0 . . ?
H3A C3 H3B 120.0 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C11 N3 Mn1 158.7(3) . 2_745 ?
C13 N6 Mn1 147.5(3) . 2_655 ?
N9 C15 N8 172.5(3) . . ?
C15 N9 Mn1 156.5(3) . 4_576 ?

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
C6 P1 C1 C2 -171.5(3) . . . . ?
C8 P1 C1 C2 65.5(3) . . . . ?
C4 P1 C1 C2 -51.7(3) . . . . ?
C6 P1 C4 C5 59.3(4) . . . . ?
C8 P1 C4 C5 179.1(3) . . . . ?
C1 P1 C4 C5 -61.8(4) . . . . ?
C6 P1 C8 C9 66.6(3) . . . . ?
C1 P1 C8 C9 -170.5(3) . . . . ?
C4 P1 C8 C9 -51.7(3) . . . . ?
P1 C1 C2 C3 110.8(4) . . . . ?
C8 P1 C6 C7 75.1(3) . . . . ?
C1 P1 C6 C7 -47.2(3) . . . . ?
C4 P1 C6 C7 -167.6(3) . . . . ?

_refine_diff_density_max         0.603
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1524209'
_audit_update_record             
;
2016-12-23 deposited with the CCDC.
2017-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 Mn N9, C8 H20 O P'
_chemical_formula_sum            'C14 H20 Mn N9 O P'
_chemical_formula_weight         416.30

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'
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'
P P 0.1023 0.0942 '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/c'

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                   10.391(13)
_cell_length_b                   15.81(2)
_cell_length_c                   15.482(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 127.560(19)
_cell_angle_gamma                90.00
_cell_volume                     2016(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5263
_cell_measurement_theta_min      1.6594
_cell_measurement_theta_max      27.4198

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             860
_exptl_absorpt_coefficient_mu    0.756
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8634
_exptl_absorpt_correction_T_max  0.8759
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  'Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16461
_diffrn_reflns_av_R_equivalents  0.0847
_diffrn_reflns_av_sigmaI/netI    0.1033
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         24.50
_reflns_number_total             3334
_reflns_number_gt                2602
_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)+(0.1600P)²+101.9335P] 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     SHELXL
_refine_ls_extinction_coef       0.066(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3334
_refine_ls_number_parameters     240
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1575
_refine_ls_R_factor_gt           0.1343
_refine_ls_wR_factor_ref         0.3438
_refine_ls_wR_factor_gt          0.3170
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.003

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 0.41640(13) 0.18386(8) 0.18495(8) 0.0238(3) Uani 1 1 d . . .
C10 C 0.4713(8) 0.3618(6) 0.3221(6) 0.029(2) Uani 1 1 d . . .
N1 N 0.4446(9) 0.3030(5) 0.2721(6) 0.046(3) Uani 1 1 d . . .
N6 N 0.4027(8) 0.1154(6) 0.3100(5) 0.036(2) Uani 1 1 d . . .
N3 N 0.6098(8) 0.5618(5) 0.3966(5) 0.031(2) Uani 1 1 d . . .
N2 N 0.5026(9) 0.4229(6) 0.3925(6) 0.057(3) Uani 1 1 d . . .
N7 N 0.6880(8) 0.1633(6) 0.3084(6) 0.046(3) Uani 1 1 d . . .
N4 N 0.4645(8) 0.2590(6) 0.0849(5) 0.038(2) Uani 1 1 d . . .
C11 C 0.5600(8) 0.4961(5) 0.3907(5) 0.022(2) Uani 1 1 d . . .
C12 C 0.4951(9) 0.3038(6) 0.0444(7) 0.033(3) Uani 1 1 d . . .
N9 N 0.1492(8) 0.2030(5) 0.0753(6) 0.041(2) Uani 1 1 d . . .
C14 C 0.7991(9) 0.1892(6) 0.3971(7) 0.038(3) Uani 1 1 d . . .
N8 N 0.9020(10) 0.2088(7) 0.4975(6) 0.068(3) Uani 1 1 d . . .
C15 C 0.0337(9) 0.2447(6) 0.0357(7) 0.034(3) Uani 1 1 d . . .
P1 P 1.0032(2) 0.01899(14) 0.76081(15) 0.0259(6) Uani 1 1 d U . .
N5 N 0.5459(8) 0.3631(6) 0.0082(5) 0.042(2) Uani 1 1 d . . .
C13 C 0.4645(9) 0.1288(6) 0.4009(6) 0.031(2) Uani 1 1 d . . .
O1 O 0.8995(7) -0.0205(5) 0.5662(4) 0.051(2) Uani 1 1 d . . .
C8 C 1.0492(8) 0.1236(6) 0.7379(6) 0.030(2) Uani 1 1 d . . .
H8A H 1.1012 0.1176 0.7019 0.036 Uiso 1 1 calc R . .
H8B H 0.9462 0.1549 0.6876 0.036 Uiso 1 1 calc R . .
C9 C 1.1633(10) 0.1767(6) 0.8445(7) 0.038(3) Uani 1 1 d . . .
H9A H 1.1044 0.1927 0.8729 0.056 Uiso 1 1 calc R . .
H9B H 1.1983 0.2278 0.8283 0.056 Uiso 1 1 calc R . .
H9C H 1.2585 0.1428 0.8990 0.056 Uiso 1 1 calc R . .
C1 C 0.8397(9) -0.0253(5) 0.6252(6) 0.030(2) Uani 1 1 d U . .
H1A H 0.8164 -0.0846 0.6318 0.036 Uiso 1 1 calc R . .
H1B H 0.7388 0.0083 0.5898 0.036 Uiso 1 1 calc R . .
C4 C 0.9355(9) 0.0242(7) 0.8461(7) 0.037(3) Uani 1 1 d . . .
H4A H 0.8976 -0.0326 0.8483 0.045 Uiso 1 1 calc R . .
H4B H 1.0297 0.0390 0.9213 0.045 Uiso 1 1 calc R . .
C7 C 1.1817(9) -0.0500(6) 0.8247(7) 0.037(3) Uani 1 1 d . . .
H7A H 1.2131 -0.0541 0.7760 0.044 Uiso 1 1 calc R . .
H7B H 1.2732 -0.0237 0.8937 0.044 Uiso 1 1 calc R . .
C5 C 0.8031(9) 0.0864(7) 0.8084(6) 0.039(3) Uani 1 1 d . . .
H5A H 0.8442 0.1438 0.8161 0.059 Uiso 1 1 calc R . .
H5B H 0.7651 0.0805 0.8525 0.059 Uiso 1 1 calc R . .
H5C H 0.7128 0.0756 0.7317 0.059 Uiso 1 1 calc R . .
C6 C 1.1554(13) -0.1379(8) 0.8487(11) 0.070(5) Uani 1 1 d . . .
H6A H 1.0821 -0.1355 0.8685 0.105 Uiso 1 1 calc R . .
H6B H 1.2598 -0.1620 0.9093 0.105 Uiso 1 1 calc R . .
H6C H 1.1072 -0.1735 0.7839 0.105 Uiso 1 1 calc R . .
C3 C 0.7876(11) -0.0444(7) 0.4554(7) 0.047(3) Uani 1 1 d . . .
H3A H 0.7418 -0.0999 0.4505 0.071 Uiso 1 1 calc R . .
H3B H 0.8436 -0.0472 0.4225 0.071 Uiso 1 1 calc R . .
H3C H 0.7002 -0.0025 0.4164 0.071 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
Mn1 N9 2.222(7) . ?
Mn1 N1 2.229(9) . ?
Mn1 N3 2.229(8) 2_645 ?
Mn1 N4 2.238(9) . ?
Mn1 N7 2.268(7) . ?
Mn1 N6 2.298(9) . ?
C10 N1 1.131(12) . ?
C10 N2 1.340(13) . ?
N6 C13 1.155(11) . ?
N3 C11 1.140(11) . ?
N3 Mn1 2.229(8) 2_655 ?
N2 C11 1.309(12) . ?
N7 C14 1.206(10) . ?
N4 C12 1.112(14) . ?
C12 N5 1.355(14) . ?
N9 C15 1.163(11) . ?
C14 N8 1.277(11) . ?
N8 C15 1.333(13) 4_666 ?
C15 N8 1.333(13) 4_465 ?
P1 C8 1.815(9) . ?
P1 C7 1.836(9) . ?
P1 C4 1.837(12) . ?
P1 C1 1.853(7) . ?
N5 C13 1.334(11) 4_565 ?
C13 N5 1.334(11) 4_566 ?
O1 C1 1.385(14) . ?
O1 C3 1.417(10) . ?
C8 C9 1.564(11) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C4 C5 1.490(14) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C7 C6 1.505(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?

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
N9 Mn1 N1 89.4(3) . . ?
N9 Mn1 N3 91.2(3) . 2_645 ?
N1 Mn1 N3 177.7(3) . 2_645 ?
N9 Mn1 N4 95.8(3) . . ?
N1 Mn1 N4 88.2(4) . . ?
N3 Mn1 N4 94.0(3) 2_645 . ?
N9 Mn1 N7 175.3(4) . . ?
N1 Mn1 N7 88.5(3) . . ?
N3 Mn1 N7 90.7(3) 2_645 . ?
N4 Mn1 N7 88.4(3) . . ?
N9 Mn1 N6 91.0(3) . . ?
N1 Mn1 N6 86.6(3) . . ?
N3 Mn1 N6 91.2(3) 2_645 . ?
N4 Mn1 N6 171.4(2) . . ?
N7 Mn1 N6 84.7(3) . . ?
N1 C10 N2 170.5(11) . . ?
C10 N1 Mn1 174.7(7) . . ?
C13 N6 Mn1 131.7(7) . . ?
C11 N3 Mn1 148.4(5) . 2_655 ?
C11 N2 C10 120.5(10) . . ?
C14 N7 Mn1 138.3(9) . . ?
C12 N4 Mn1 171.5(8) . . ?
N3 C11 N2 173.9(10) . . ?
N4 C12 N5 172.5(9) . . ?
C15 N9 Mn1 152.6(7) . . ?
N7 C14 N8 168.3(12) . . ?
C14 N8 C15 123.1(11) . 4_666 ?
N9 C15 N8 175.4(12) . 4_465 ?
C8 P1 C7 110.3(4) . . ?
C8 P1 C4 111.2(5) . . ?
C7 P1 C4 110.0(5) . . ?
C8 P1 C1 107.0(4) . . ?
C7 P1 C1 108.3(4) . . ?
C4 P1 C1 110.0(4) . . ?
C13 N5 C12 118.1(7) 4_565 . ?
N6 C13 N5 173.8(10) . 4_566 ?
C1 O1 C3 114.7(7) . . ?
C9 C8 P1 113.8(6) . . ?
C9 C8 H8A 108.8 . . ?
P1 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
P1 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C1 P1 104.8(5) . . ?
O1 C1 H1A 110.8 . . ?
P1 C1 H1A 110.8 . . ?
O1 C1 H1B 110.8 . . ?
P1 C1 H1B 110.8 . . ?
H1A C1 H1B 108.9 . . ?
C5 C4 P1 114.5(7) . . ?
C5 C4 H4A 108.6 . . ?
P1 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
P1 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C6 C7 P1 114.0(8) . . ?
C6 C7 H7A 108.8 . . ?
P1 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
P1 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C3 H3A 109.5 . . ?
O1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
O1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C10 N1 Mn1 -77(13) . . . . ?
N9 Mn1 N1 C10 172(10) . . . . ?
N3 Mn1 N1 C10 67(15) 2_645 . . . ?
N4 Mn1 N1 C10 -92(10) . . . . ?
N7 Mn1 N1 C10 -4(10) . . . . ?
N6 Mn1 N1 C10 81(10) . . . . ?
N9 Mn1 N6 C13 -122.6(10) . . . . ?
N1 Mn1 N6 C13 -33.3(9) . . . . ?
N3 Mn1 N6 C13 146.2(9) 2_645 . . . ?
N4 Mn1 N6 C13 20(3) . . . . ?
N7 Mn1 N6 C13 55.6(10) . . . . ?
N1 C10 N2 C11 163(5) . . . . ?
N9 Mn1 N7 C14 -47(5) . . . . ?
N1 Mn1 N7 C14 16.3(13) . . . . ?
N3 Mn1 N7 C14 -161.5(13) 2_645 . . . ?
N4 Mn1 N7 C14 104.5(13) . . . . ?
N6 Mn1 N7 C14 -70.4(13) . . . . ?
N9 Mn1 N4 C12 104(5) . . . . ?
N1 Mn1 N4 C12 15(5) . . . . ?
N3 Mn1 N4 C12 -164(5) 2_645 . . . ?
N7 Mn1 N4 C12 -74(5) . . . . ?
N6 Mn1 N4 C12 -38(6) . . . . ?
Mn1 N3 C11 N2 -123(6) 2_655 . . . ?
C10 N2 C11 N3 180(100) . . . . ?
Mn1 N4 C12 N5 22(12) . . . . ?
N1 Mn1 N9 C15 18(2) . . . . ?
N3 Mn1 N9 C15 -164(2) 2_645 . . . ?
N4 Mn1 N9 C15 -70(2) . . . . ?
N7 Mn1 N9 C15 82(5) . . . . ?
N6 Mn1 N9 C15 105(2) . . . . ?
Mn1 N7 C14 N8 67(6) . . . . ?
N7 C14 N8 C15 180(100) . . . 4_666 ?
Mn1 N9 C15 N8 -84(13) . . . 4_465 ?
N4 C12 N5 C13 -169(8) . . . 4_565 ?
Mn1 N6 C13 N5 -108(10) . . . 4_566 ?
C7 P1 C8 C9 -72.6(8) . . . . ?
C4 P1 C8 C9 49.8(7) . . . . ?
C1 P1 C8 C9 169.9(7) . . . . ?
C3 O1 C1 P1 -174.7(7) . . . . ?
C8 P1 C1 O1 55.0(7) . . . . ?
C7 P1 C1 O1 -63.9(7) . . . . ?
C4 P1 C1 O1 175.8(6) . . . . ?
C8 P1 C4 C5 50.8(7) . . . . ?
C7 P1 C4 C5 173.3(6) . . . . ?
C1 P1 C4 C5 -67.5(8) . . . . ?
C8 P1 C7 C6 178.9(8) . . . . ?
C4 P1 C7 C6 55.9(10) . . . . ?
C1 P1 C7 C6 -64.3(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1B N5 0.99 2.58 3.526(12) 159.7 4_566
C1 H1B N5 0.99 2.58 3.526(12) 159.7 4_566
C1 H1B N5 0.99 2.58 3.526(12) 159.7 4_566
C1 H1B N5 0.99 2.58 3.526(12) 159.7 4_566
C1 H1B N5 0.99 2.58 3.526(12) 159.7 4_566
C1 H1B N5 0.99 2.58 3.526(12) 159.7 4_566
C1 H1B N5 0.99 2.58 3.526(12) 159.7 4_566
C1 H1B N5 0.99 2.58 3.526(12) 159.7 4_566
C1 H1B N5 0.99 2.58 3.526(12) 159.7 4_566
C1 H1B N5 0.99 2.58 3.526(12) 159.7 4_566
C1 H1B N5 0.99 2.58 3.526(12) 159.7 4_566

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        24.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.785
_refine_diff_density_min         -1.022
_refine_diff_density_rms         0.268
####################################################################### 
# 
# 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 1515779'
_audit_update_record             
;
2016-11-18 deposited with the CCDC.
2017-01-10 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         'C6 Mn N9,C9 H22 P'
_chemical_formula_sum            'C15 H22 Mn N9 P'
_chemical_formula_weight         414.32

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'
P P 0.1023 0.0942 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.496(2)
_cell_length_b                   12.396(3)
_cell_length_c                   16.254(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2114.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2656
_cell_measurement_theta_min      2.3125
_cell_measurement_theta_max      26.9805

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             860
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.717
_shelx_estimated_absorpt_T_min   0.870
_shelx_estimated_absorpt_T_max   0.870
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14796
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.170
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4818
_reflns_number_gt                3564
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0626P)²+0.7456P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.14(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4818
_refine_ls_number_parameters     240
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1376
_refine_ls_wR_factor_gt          0.1250
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_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
C1 C 0.7628(12) 0.8866(6) 0.0292(5) 0.098(3) Uani 1 1 d . . . . .
H1A H 0.7700 0.8563 0.0840 0.118 Uiso 1 1 calc R U . . .
H1B H 0.6732 0.8861 0.0145 0.118 Uiso 1 1 calc R U . . .
C2 C 0.8307(11) 0.8161(7) -0.0278(6) 0.109(3) Uani 1 1 d . . . . .
H2A H 0.9210 0.8196 -0.0153 0.131 Uiso 1 1 calc R U . . .
H2B H 0.8193 0.8437 -0.0832 0.131 Uiso 1 1 calc R U . . .
C3 C 0.7900(13) 0.6999(7) -0.0264(6) 0.125(4) Uani 1 1 d . . . . .
H3A H 0.8041 0.6706 0.0275 0.187 Uiso 1 1 calc R U . . .
H3B H 0.8387 0.6599 -0.0660 0.187 Uiso 1 1 calc R U . . .
H3C H 0.7011 0.6951 -0.0398 0.187 Uiso 1 1 calc R U . . .
C4 C 0.8103(9) 1.0856(7) -0.0664(5) 0.098(3) Uani 1 1 d . . . . .
H4A H 0.8393 1.1596 -0.0612 0.118 Uiso 1 1 calc R U . . .
H4B H 0.8701 1.0484 -0.1020 0.118 Uiso 1 1 calc R U . . .
C5 C 0.6825(11) 1.0863(10) -0.1077(7) 0.126(4) Uani 1 1 d . . . . .
H5A H 0.6558 1.0134 -0.1180 0.189 Uiso 1 1 calc R U . . .
H5B H 0.6883 1.1246 -0.1589 0.189 Uiso 1 1 calc R U . . .
H5C H 0.6215 1.1213 -0.0727 0.189 Uiso 1 1 calc R U . . .
C6 C 0.7141(8) 1.0972(7) 0.1031(5) 0.086(2) Uani 1 1 d . . . . .
H6A H 0.7414 1.1720 0.1045 0.103 Uiso 1 1 calc R U . . .
H6B H 0.6276 1.0958 0.0821 0.103 Uiso 1 1 calc R U . . .
C7 C 0.7137(10) 1.0542(7) 0.1890(5) 0.114(3) Uani 1 1 d . . . . .
H7A H 0.6823 0.9815 0.1888 0.172 Uiso 1 1 calc R U . . .
H7B H 0.6597 1.0982 0.2228 0.172 Uiso 1 1 calc R U . . .
H7C H 0.7989 1.0552 0.2105 0.172 Uiso 1 1 calc R U . . .
C8 C 0.9779(8) 1.0306(7) 0.0681(6) 0.092(3) Uani 1 1 d . . . . .
H8A H 0.9845 0.9923 0.1199 0.110 Uiso 1 1 calc R U . . .
H8B H 1.0321 0.9941 0.0286 0.110 Uiso 1 1 calc R U . . .
C9 C 1.0263(8) 1.1450(8) 0.0799(6) 0.097(3) Uani 1 1 d . . . . .
H9A H 1.0464 1.1759 0.0273 0.146 Uiso 1 1 calc R U . . .
H9B H 1.1014 1.1438 0.1136 0.146 Uiso 1 1 calc R U . . .
H9C H 0.9617 1.1875 0.1063 0.146 Uiso 1 1 calc R U . . .
C10 C 0.3289(6) 1.1054(5) 0.9844(3) 0.0508(14) Uani 1 1 d . . . . .
C11 C 0.3525(6) 1.0629(6) 1.1187(3) 0.0566(15) Uani 1 1 d . . . . .
C12 C 0.0862(6) 0.8380(6) 0.8342(4) 0.0582(17) Uani 1 1 d . . . . .
C13 C 0.0042(7) 0.6998(5) 0.7599(5) 0.0604(16) Uani 1 1 d . . . . .
C14 C 0.4439(9) 0.8581(9) 0.8188(5) 0.099(3) Uani 1 1 d . U . . .
C15 C 0.5821(9) 0.7186(7) 0.7940(5) 0.092(3) Uani 1 1 d . U . . .
Mn1 Mn 0.22651(8) 1.04889(6) 0.79988(4) 0.0405(2) Uani 1 1 d . . . . .
N1 N 0.2812(6) 1.1098(4) 0.9224(3) 0.0623(13) Uani 1 1 d . . . . .
N2 N 0.3909(6) 1.1126(7) 1.0524(3) 0.093(3) Uani 1 1 d . . . . .
N3 N 0.3285(6) 1.0229(5) 1.1785(3) 0.0705(16) Uani 1 1 d . . . . .
N4 N 0.0975(6) 0.9239(5) 0.8571(3) 0.0632(14) Uani 1 1 d . . . . .
N5 N 0.0865(7) 0.7361(4) 0.8127(5) 0.089(2) Uani 1 1 d . . . . .
N6 N -0.0625(6) 0.6601(4) 0.7131(4) 0.0719(16) Uani 1 1 d . . . . .
N7 N 0.3832(6) 0.9290(5) 0.8087(4) 0.0794(17) Uani 1 1 d . . . . .
N8 N 0.5165(11) 0.7787(8) 0.8442(6) 0.146(3) Uani 1 1 d . U . . .
N9 N 0.6464(7) 0.6653(5) 0.7602(4) 0.0806(18) Uani 1 1 d . . . . .
P1 P 0.81561(18) 1.02408(14) 0.03278(12) 0.0651(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
C1 C2 1.460(12) . ?
C1 P1 1.793(8) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.502(11) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.501(13) . ?
C4 P1 1.785(9) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.494(11) . ?
C6 P1 1.807(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.518(11) . ?
C8 P1 1.799(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N1 1.127(7) . ?
C10 N2 1.286(8) . ?
C11 N3 1.119(7) . ?
C11 N2 1.305(8) . ?
C12 N4 1.134(8) . ?
C12 N5 1.311(9) . ?
C13 N6 1.145(9) . ?
C13 N5 1.298(9) . ?
C14 N7 1.097(9) . ?
C14 N8 1.312(12) . ?
C15 N9 1.092(8) . ?
C15 N8 1.303(11) . ?
Mn1 N9 2.194(6) 3_656 ?
Mn1 N1 2.206(5) . ?
Mn1 N6 2.216(6) 3_556 ?
Mn1 N7 2.222(6) . ?
Mn1 N3 2.240(5) 2_574 ?
Mn1 N4 2.258(6) . ?
N3 Mn1 2.240(5) 2_575 ?
N6 Mn1 2.216(6) 3_546 ?
N9 Mn1 2.194(6) 3_646 ?

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
C2 C1 P1 116.0(7) . . ?
C2 C1 H1A 108.3 . . ?
P1 C1 H1A 108.3 . . ?
C2 C1 H1B 108.3 . . ?
P1 C1 H1B 108.3 . . ?
H1A C1 H1B 107.4 . . ?
C1 C2 C3 115.2(9) . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 . . ?
C3 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 P1 115.8(7) . . ?
C5 C4 H4A 108.3 . . ?
P1 C4 H4A 108.3 . . ?
C5 C4 H4B 108.3 . . ?
P1 C4 H4B 108.3 . . ?
H4A C4 H4B 107.4 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 P1 114.4(6) . . ?
C7 C6 H6A 108.7 . . ?
P1 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
P1 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 P1 113.5(6) . . ?
C9 C8 H8A 108.9 . . ?
P1 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
P1 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 N2 172.1(7) . . ?
N3 C11 N2 174.3(7) . . ?
N4 C12 N5 172.7(7) . . ?
N6 C13 N5 174.3(8) . . ?
N7 C14 N8 170.1(10) . . ?
N9 C15 N8 171.1(10) . . ?
N9 Mn1 N1 91.1(2) 3_656 . ?
N9 Mn1 N6 91.2(3) 3_656 3_556 ?
N1 Mn1 N6 94.3(2) . 3_556 ?
N9 Mn1 N7 91.1(3) 3_656 . ?
N1 Mn1 N7 88.8(2) . . ?
N6 Mn1 N7 176.2(2) 3_556 . ?
N9 Mn1 N3 91.5(2) 3_656 2_574 ?
N1 Mn1 N3 176.6(2) . 2_574 ?
N6 Mn1 N3 87.9(2) 3_556 2_574 ?
N7 Mn1 N3 89.0(2) . 2_574 ?
N9 Mn1 N4 177.5(2) 3_656 . ?
N1 Mn1 N4 91.1(2) . . ?
N6 Mn1 N4 90.0(2) 3_556 . ?
N7 Mn1 N4 87.6(2) . . ?
N3 Mn1 N4 86.3(2) 2_574 . ?
C10 N1 Mn1 155.1(5) . . ?
C10 N2 C11 121.3(6) . . ?
C11 N3 Mn1 176.7(6) . 2_575 ?
C12 N4 Mn1 124.8(5) . . ?
C13 N5 C12 120.5(6) . . ?
C13 N6 Mn1 143.6(6) . 3_546 ?
C14 N7 Mn1 167.2(8) . . ?
C15 N8 C14 122.6(8) . . ?
C15 N9 Mn1 175.5(7) . 3_646 ?
C4 P1 C1 111.5(4) . . ?
C4 P1 C8 107.4(4) . . ?
C1 P1 C8 110.2(5) . . ?
C4 P1 C6 109.8(4) . . ?
C1 P1 C6 108.4(4) . . ?
C8 P1 C6 109.5(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
C6 H6B N2 0.97 2.54 3.496(11) 168.8 1_554

_refine_diff_density_max         0.580
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1515782'
_audit_update_record             
;
2016-11-18 deposited with the CCDC.
2017-01-10 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         'C6 Mn N9,C8 H20 O P'
_chemical_formula_sum            'C14 H20 Mn N9 O P'
_chemical_formula_weight         416.30

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'
P P 0.1023 0.0942 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.694(2)
_cell_length_b                   12.092(2)
_cell_length_c                   16.108(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2083.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2752
_cell_measurement_theta_min      2.2052
_cell_measurement_theta_max      26.7893

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_F_000             860
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.732
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14569
_diffrn_reflns_av_unetI/netI     0.0774
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.039
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4760
_reflns_number_gt                3164
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    0.999

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0758P)²+0.0779P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.00(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4760
_refine_ls_number_parameters     240
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1537
_refine_ls_wR_factor_gt          0.1338
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.072
_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
C8 C 0.5287(10) 0.5149(8) 0.9347(7) 0.101(3) Uani 1 1 d . . . . .
H8A H 0.5233 0.4768 0.8819 0.122 Uiso 1 1 calc R U . . .
H8B H 0.4798 0.4735 0.9748 0.122 Uiso 1 1 calc R U . . .
C5 C 0.8215(11) 0.5891(13) 1.1042(8) 0.146(5) Uani 1 1 d . . . . .
H5A H 0.8485 0.5168 1.1209 0.219 Uiso 1 1 calc R U . . .
H5B H 0.8200 0.6372 1.1516 0.219 Uiso 1 1 calc R U . . .
H5C H 0.8782 0.6181 1.0634 0.219 Uiso 1 1 calc R U . . .
C4 C 0.6952(10) 0.5820(8) 1.0683(6) 0.097(3) Uani 1 1 d . . . . .
H4A H 0.6609 0.6559 1.0638 0.116 Uiso 1 1 calc R U . . .
H4B H 0.6422 0.5403 1.1059 0.116 Uiso 1 1 calc R U . . .
C6 C 0.7843(9) 0.5942(7) 0.8949(6) 0.085(2) Uani 1 1 d . . . . .
H6A H 0.7546 0.6699 0.8931 0.102 Uiso 1 1 calc R U . . .
H6B H 0.8702 0.5956 0.9143 0.102 Uiso 1 1 calc R U . . .
C1 C 0.7492(14) 0.3784(7) 0.9737(7) 0.118(4) Uani 1 1 d . . . . .
H1A H 0.7382 0.3417 0.9206 0.141 Uiso 1 1 calc R U . . .
H1B H 0.8376 0.3786 0.9872 0.141 Uiso 1 1 calc R U . . .
P1 P 0.69110(19) 0.51792(16) 0.96824(14) 0.0688(6) Uani 1 1 d . . . . .
C10 C 0.1670(7) 0.6079(6) 0.0113(4) 0.0576(17) Uani 1 1 d . U . . .
C14 C 0.4171(7) 0.3400(6) 0.1610(4) 0.0596(19) Uani 1 1 d . . . . .
N4 N 0.1238(6) 0.4279(5) 0.1871(5) 0.0832(19) Uani 1 1 d . . . . .
N7 N 0.4027(6) 0.4268(5) 0.1349(4) 0.0638(16) Uani 1 1 d . . . . .
N1 N 0.2147(7) 0.6173(5) 0.0730(3) 0.0646(15) Uani 1 1 d . . . . .
Mn1 Mn 0.27545(9) 0.55427(7) 0.19451(5) 0.0412(3) Uani 1 1 d . . . . .
N8 N 0.4213(7) 0.2378(5) 0.1864(6) 0.089(2) Uani 1 1 d . . . . .
N2 N 0.1014(7) 0.6073(8) -0.0565(4) 0.093(2) Uani 1 1 d . U . . .
N5 N 0.0019(11) 0.2668(9) 0.1592(7) 0.146(3) Uani 1 1 d . U . . .
C9 C 0.4731(10) 0.6300(10) 0.9255(8) 0.118(4) Uani 1 1 d . . . . .
H9A H 0.4623 0.6625 0.9794 0.178 Uiso 1 1 calc R U . . .
H9B H 0.3935 0.6250 0.8983 0.178 Uiso 1 1 calc R U . . .
H9C H 0.5284 0.6752 0.8931 0.178 Uiso 1 1 calc R U . . .
C12 C 0.0641(10) 0.3548(8) 0.1796(6) 0.097(3) Uani 1 1 d . U . . .
C7 C 0.7819(10) 0.5475(7) 0.8085(6) 0.106(3) Uani 1 1 d . . . . .
H7A H 0.8087 0.4718 0.8098 0.158 Uiso 1 1 calc R U . . .
H7B H 0.8372 0.5894 0.7737 0.158 Uiso 1 1 calc R U . . .
H7C H 0.6984 0.5516 0.7869 0.158 Uiso 1 1 calc R U . . .
O1 O 0.6828(10) 0.3243(6) 1.0343(5) 0.149(4) Uani 1 1 d . . . . .
C3 C 0.7038(16) 0.2128(8) 1.0361(8) 0.148(6) Uani 1 1 d . . . . .
H3A H 0.6324 0.1748 1.0140 0.223 Uiso 1 1 calc R U . . .
H3B H 0.7176 0.1897 1.0924 0.223 Uiso 1 1 calc R U . . .
H3C H 0.7762 0.1957 1.0033 0.223 Uiso 1 1 calc R U . . .
C13 C -0.0785(10) 0.2186(8) 0.2098(6) 0.100(3) Uani 1 1 d . U . . .
N6 N -0.1484(7) 0.1706(6) 0.2434(4) 0.0775(19) Uani 1 1 d . . . . .
N3 N 0.1684(6) 0.5176(5) -0.1839(4) 0.0731(17) Uani 1 1 d . . . . .
C11 C 0.1424(7) 0.5575(7) -0.1232(4) 0.0642(18) Uani 1 1 d . U . . .
N9 N 0.5652(6) 0.1700(5) 0.2931(5) 0.0703(18) Uani 1 1 d . . . . .
C15 C 0.5013(8) 0.2067(5) 0.2421(6) 0.0640(19) 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
C8 C9 1.520(14) . ?
C8 P1 1.819(11) . ?
C5 C4 1.470(14) . ?
C4 P1 1.789(9) . ?
C6 C7 1.501(13) . ?
C6 P1 1.800(8) . ?
C1 O1 1.373(12) . ?
C1 P1 1.800(10) . ?
C10 N1 1.124(8) . ?
C10 N2 1.297(9) . ?
C14 N7 1.141(9) . ?
C14 N8 1.303(10) . ?
N4 C12 1.097(10) . ?
N4 Mn1 2.232(6) . ?
N7 Mn1 2.269(6) . ?
N1 Mn1 2.198(6) . ?
Mn1 N6 2.196(7) 3 ?
Mn1 N9 2.213(6) 3_655 ?
Mn1 N3 2.225(6) 2_565 ?
N8 C15 1.296(11) . ?
N2 C11 1.307(9) . ?
N5 C12 1.296(12) . ?
N5 C13 1.322(12) . ?
O1 C3 1.367(11) . ?
C13 N6 1.090(10) . ?
N6 Mn1 2.196(7) 3_545 ?
N3 C11 1.126(8) . ?
N3 Mn1 2.225(6) 2_564 ?
N9 C15 1.157(10) . ?
N9 Mn1 2.213(6) 3_645 ?

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
C9 C8 P1 112.6(6) . . ?
C5 C4 P1 113.7(9) . . ?
C7 C6 P1 114.0(6) . . ?
O1 C1 P1 107.6(8) . . ?
C4 P1 C1 110.7(5) . . ?
C4 P1 C6 110.9(5) . . ?
C1 P1 C6 108.7(5) . . ?
C4 P1 C8 107.4(5) . . ?
C1 P1 C8 109.0(6) . . ?
C6 P1 C8 110.1(5) . . ?
N1 C10 N2 172.1(8) . . ?
N7 C14 N8 173.3(8) . . ?
C12 N4 Mn1 168.7(8) . . ?
C14 N7 Mn1 123.3(6) . . ?
C10 N1 Mn1 152.5(6) . . ?
N6 Mn1 N1 90.0(3) 3 . ?
N6 Mn1 N9 91.7(3) 3 3_655 ?
N1 Mn1 N9 95.1(3) . 3_655 ?
N6 Mn1 N3 90.9(3) 3 2_565 ?
N1 Mn1 N3 177.0(2) . 2_565 ?
N9 Mn1 N3 87.7(3) 3_655 2_565 ?
N6 Mn1 N4 90.8(3) 3 . ?
N1 Mn1 N4 88.6(3) . . ?
N9 Mn1 N4 175.6(3) 3_655 . ?
N3 Mn1 N4 88.6(3) 2_565 . ?
N6 Mn1 N7 176.9(3) 3 . ?
N1 Mn1 N7 92.1(2) . . ?
N9 Mn1 N7 90.3(2) 3_655 . ?
N3 Mn1 N7 86.9(2) 2_565 . ?
N4 Mn1 N7 87.0(2) . . ?
C15 N8 C14 121.0(7) . . ?
C10 N2 C11 120.8(6) . . ?
C12 N5 C13 122.6(9) . . ?
N4 C12 N5 170.9(11) . . ?
C3 O1 C1 113.6(9) . . ?
N6 C13 N5 171.0(10) . . ?
C13 N6 Mn1 172.4(8) . 3_545 ?
C11 N3 Mn1 177.4(7) . 2_564 ?
N3 C11 N2 174.0(8) . . ?
C15 N9 Mn1 139.6(7) . 3_645 ?
N9 C15 N8 173.2(9) . . ?

_refine_diff_density_max         0.459
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.076

