# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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 2265206'
loop_
_audit_author_name
_audit_author_address
'ke xu'
;Southeast University
China
;
_audit_update_record             
;
2023-05-24 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;
_audit_creation_date             2023-03-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H21 Mn N6 O P'
_chemical_formula_sum            'C13 H21 Mn N6 O P'
_chemical_formula_weight         363.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.7272(6)
_cell_length_b                   13.4618(9)
_cell_length_c                   15.5199(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.731(6)
_cell_angle_gamma                90
_cell_volume                     1823.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2470
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.003
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.821
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             756
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12914
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.003
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2470
_reflns_number_total             3209
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.907
_refine_diff_density_min         -1.033
_refine_diff_density_rms         0.144
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3209
_refine_ls_number_restraints     74
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0731
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1556P)²+1.1900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2240
_refine_ls_wR_factor_ref         0.2386
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1-H1
 0.98 with sigma of 0.01
3. Rigid bond restraints
 P1, O1
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0001
 P1, C1
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0001
 P1, C4
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0001
 P1, C7
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0001
 C12, C10, C11, C13, C7, C4, C9, C5, C8, C6, C3, C1, C2
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
 C2, C1, C3, C8, C7, C4, C9, C6, C5
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C6 \\sim C5 \\sim C4 \\sim C3 \\sim C1 \\sim C2 \\sim C7 \\sim C8 \\sim C9:
within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
Uanis(P1) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C1) \\sim
Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C2) = Uanis(C6) = Uanis(C8) = Uanis(C9)
5.a Ternary CH refined with riding coordinates:
 C7(H7), C4(H4), C1(H1)
5.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C5(H5A,H5B,H5C), C8(H8A,H8B,H8C), C6(H6A,H6B,H6C), C3(H3A,
 H3B,H3C), C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.74577(5) 0.12023(3) -0.07653(3) 0.03664(13) Uani 1 1 d . . . . .
C12 C 1.1174(4) 0.0771(2) -0.0409(2) 0.0440(8) Uani 1 1 d . . . . .
N6 N 0.4962(3) 0.0901(2) -0.0734(2) 0.0533(8) Uani 1 1 d . . . . .
N5 N 1.2489(3) 0.0374(2) -0.0146(2) 0.0528(8) Uani 1 1 d . . . . .
C10 C 0.3773(3) 0.0691(2) -0.0488(2) 0.0417(8) Uani 1 1 d . . . . .
N4 N 0.9971(3) 0.1052(2) -0.0578(2) 0.0558(8) Uani 1 1 d . . . . .
O1 O 0.7294(3) 0.1908(2) 0.04335(16) 0.0614(5) Uani 1 1 d . U . . .
N1 N 0.7394(4) 0.2635(2) -0.1418(2) 0.0619(9) Uani 1 1 d . . . . .
N3 N 0.7599(4) 0.0333(3) -0.1957(2) 0.0673(10) Uani 1 1 d . . . . .
P1 P 0.71818(15) 0.25872(10) 0.11770(8) 0.07761(11) Uani 1 1 d . U . . .
C11 C 0.7565(6) -0.0137(3) -0.2564(3) 0.0683(12) Uani 1 1 d . . . . .
C13 C 0.7422(5) 0.3465(3) -0.1592(2) 0.0634(11) Uani 1 1 d . . . . .
C7 C 0.5273(7) 0.3095(5) 0.1255(4) 0.1206(7) Uani 1 1 d . U . . .
H7 H 0.526848 0.359508 0.171390 0.145 Uiso 1 1 calc R U . . .
C4 C 0.7533(8) 0.1815(6) 0.2157(4) 0.1196(6) Uani 1 1 d . U . . .
H4 H 0.676473 0.128595 0.211173 0.144 Uiso 1 1 calc R U . . .
C9 C 0.4081(10) 0.2329(6) 0.1444(5) 0.1572(7) Uani 1 1 d . U . . .
H9A H 0.363276 0.209588 0.091365 0.236 Uiso 1 1 calc R U . . .
H9B H 0.329878 0.261745 0.179465 0.236 Uiso 1 1 calc R U . . .
H9C H 0.454577 0.178178 0.174637 0.236 Uiso 1 1 calc R U . . .
C5 C 0.9016(9) 0.1279(7) 0.2136(5) 0.1722(12) Uani 1 1 d . U . . .
H5A H 0.965286 0.149473 0.260912 0.258 Uiso 1 1 calc R U . . .
H5B H 0.951883 0.141686 0.160314 0.258 Uiso 1 1 calc R U . . .
H5C H 0.883555 0.057748 0.218359 0.258 Uiso 1 1 calc R U . . .
C8 C 0.4702(10) 0.3574(6) 0.0421(5) 0.1572(7) Uani 1 1 d . U . . .
H8A H 0.531543 0.414697 0.029637 0.236 Uiso 1 1 calc R U . . .
H8B H 0.365223 0.377094 0.048285 0.236 Uiso 1 1 calc R U . . .
H8C H 0.477921 0.310504 -0.004306 0.236 Uiso 1 1 calc R U . . .
C6 C 0.7235(9) 0.2296(7) 0.3072(4) 0.1572(7) Uani 1 1 d . U . . .
H6A H 0.819077 0.251105 0.332146 0.236 Uiso 1 1 calc R U . . .
H6B H 0.677129 0.181317 0.344107 0.236 Uiso 1 1 calc R U . . .
H6C H 0.656233 0.285619 0.300597 0.236 Uiso 1 1 calc R U . . .
N2 N 0.7461(7) 0.4420(3) -0.1685(3) 0.1138(19) Uani 1 1 d . . . . .
C3 C 0.9776(9) 0.3523(6) 0.0596(6) 0.2002(13) Uani 1 1 d . U . . .
H3A H 0.998649 0.412968 0.029487 0.300 Uiso 1 1 calc R U . . .
H3B H 0.964770 0.299248 0.018729 0.300 Uiso 1 1 calc R U . . .
H3C H 1.061549 0.337111 0.097931 0.300 Uiso 1 1 calc R U . . .
C1 C 0.8457(9) 0.3629(5) 0.1062(6) 0.1446(8) Uani 1 1 d D U . . .
H1 H 0.785359 0.402346 0.064886 0.174 Uiso 1 1 calc DR U . . .
C2 C 0.8562(10) 0.4337(6) 0.1755(5) 0.1572(7) Uani 1 1 d . U . . .
H2A H 0.784838 0.416053 0.219537 0.236 Uiso 1 1 calc R U . . .
H2B H 0.832406 0.498808 0.154036 0.236 Uiso 1 1 calc R U . . .
H2C H 0.958319 0.433292 0.199227 0.236 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 N6 2.217(3) . ?
Mn1 N5 2.551(3) 3_755 ?
Mn1 N4 2.218(3) . ?
Mn1 O1 2.096(3) . ?
Mn1 N1 2.179(3) . ?
Mn1 N3 2.193(3) . ?
C12 N5 1.325(4) . ?
C12 N4 1.143(4) . ?
N6 C10 1.146(4) . ?
N5 C10 1.316(4) 1_655 ?
O1 P1 1.476(3) . ?
N1 C13 1.149(5) . ?
N3 C11 1.134(5) . ?
P1 C7 1.806(6) . ?
P1 C4 1.865(7) . ?
P1 C1 1.801(7) . ?
C11 N2 1.310(6) 2_644 ?
C13 N2 1.295(6) . ?
C7 H7 0.9800 . ?
C7 C9 1.497(10) . ?
C7 C8 1.525(10) . ?
C4 H4 0.9800 . ?
C4 C5 1.482(10) . ?
C4 C6 1.585(9) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C3 C1 1.375(11) . ?
C1 H1 0.9800 . ?
C1 C2 1.439(10) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?

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
N6 Mn1 N5 81.16(10) . 3_755 ?
N6 Mn1 N4 161.91(12) . . ?
N4 Mn1 N5 80.80(10) . 3_755 ?
O1 Mn1 N6 89.15(11) . . ?
O1 Mn1 N5 83.44(11) . 3_755 ?
O1 Mn1 N4 90.20(12) . . ?
O1 Mn1 N1 90.55(11) . . ?
O1 Mn1 N3 174.69(12) . . ?
N1 Mn1 N6 98.82(12) . . ?
N1 Mn1 N5 173.99(11) . 3_755 ?
N1 Mn1 N4 99.26(12) . . ?
N1 Mn1 N3 94.70(12) . . ?
N3 Mn1 N6 89.25(13) . . ?
N3 Mn1 N5 91.31(12) . 3_755 ?
N3 Mn1 N4 89.75(13) . . ?
N4 C12 N5 173.1(4) . . ?
C10 N6 Mn1 161.3(3) . . ?
C12 N5 Mn1 121.1(2) . 3_755 ?
C10 N5 Mn1 118.9(2) 1_655 3_755 ?
C10 N5 C12 118.9(3) 1_655 . ?
N6 C10 N5 173.3(4) . 1_455 ?
C12 N4 Mn1 164.6(3) . . ?
P1 O1 Mn1 168.68(19) . . ?
C13 N1 Mn1 165.7(3) . . ?
C11 N3 Mn1 175.0(4) . . ?
O1 P1 C7 110.9(2) . . ?
O1 P1 C4 106.3(3) . . ?
O1 P1 C1 111.0(3) . . ?
C7 P1 C4 107.3(3) . . ?
C1 P1 C7 106.5(3) . . ?
C1 P1 C4 114.8(4) . . ?
N3 C11 N2 173.2(5) . 2_644 ?
N1 C13 N2 172.8(4) . . ?
P1 C7 H7 108.8 . . ?
C9 C7 P1 113.4(5) . . ?
C9 C7 H7 108.8 . . ?
C9 C7 C8 103.7(6) . . ?
C8 C7 P1 113.2(5) . . ?
C8 C7 H7 108.8 . . ?
P1 C4 H4 104.0 . . ?
C5 C4 P1 112.9(5) . . ?
C5 C4 H4 104.0 . . ?
C5 C4 C6 111.8(6) . . ?
C6 C4 P1 118.4(6) . . ?
C6 C4 H4 104.0 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C13 N2 C11 123.5(4) . 2_654 ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
P1 C1 H1 99.2 . . ?
C3 C1 P1 119.6(6) . . ?
C3 C1 H1 99.2 . . ?
C3 C1 C2 114.6(7) . . ?
C2 C1 P1 118.3(6) . . ?
C2 C1 H1 99.2 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 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
Mn1 O1 P1 C7 75.6(10) . . . . ?
Mn1 O1 P1 C4 -168.0(9) . . . . ?
Mn1 O1 P1 C1 -42.5(10) . . . . ?
O1 P1 C7 C9 65.0(5) . . . . ?
O1 P1 C7 C8 -52.8(6) . . . . ?
O1 P1 C4 C5 56.1(6) . . . . ?
O1 P1 C4 C6 -170.6(5) . . . . ?
O1 P1 C1 C3 -28.1(9) . . . . ?
O1 P1 C1 C2 -176.3(6) . . . . ?
C7 P1 C4 C5 174.8(6) . . . . ?
C7 P1 C4 C6 -51.8(6) . . . . ?
C7 P1 C1 C3 -148.9(8) . . . . ?
C7 P1 C1 C2 62.8(7) . . . . ?
C4 P1 C7 C9 -50.7(6) . . . . ?
C4 P1 C7 C8 -168.5(5) . . . . ?
C4 P1 C1 C3 92.4(8) . . . . ?
C4 P1 C1 C2 -55.8(8) . . . . ?
C1 P1 C7 C9 -174.2(5) . . . . ?
C1 P1 C7 C8 68.0(6) . . . . ?
C1 P1 C4 C5 -67.0(7) . . . . ?
C1 P1 C4 C6 66.3(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_new
_database_code_depnum_ccdc_archive 'CCDC 2265207'
loop_
_audit_author_name
_audit_author_address
'ke xu'
;Southeast University
China
;
_audit_update_record             
;
2023-05-24 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;
_audit_creation_date             2023-05-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 Mn N6 O P'
_chemical_formula_sum            'C13 Mn N6 O P'
_chemical_formula_weight         342.10
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P m n b'
_space_group_name_Hall           '-P 2bc 2a'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'x+1/2, -y, -z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x-1/2, y, z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.7333(3)
_cell_length_b                   13.8646(7)
_cell_length_c                   15.4301(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1868.33(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1820
_cell_measurement_temperature    408(2)
_cell_measurement_theta_max      30.928
_cell_measurement_theta_min      3
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.801
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             748
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.816
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9549
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.816
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.928
_diffrn_reflns_theta_min         1.975
_diffrn_ambient_temperature      408(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.816
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1820
_reflns_number_total             2556
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     107
_refine_ls_number_reflns         2556
_refine_ls_number_restraints     115
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0700
_refine_ls_restrained_S_all      2.042
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1827P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2264
_refine_ls_wR_factor_ref         0.2443
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 P1-O1
 1.6 with sigma of 0.01
 Mn1-O1
 2.1 with sigma of 0.01
 P1-C2A = C6A-C4 = C5A-C4 = C3A-C1 = C2A-C1
 1.6 with sigma of 0.02
 P1-C2A
 4 with sigma of 0.02
 C3A-C2A
 2.5 with sigma of 0.02
 C4-C5 \\sim C4-C5A
 with sigma of 0.02
 C4-C6 \\sim C4-C6A
 with sigma of 0.02
 C1-C2 \\sim C1-C2A
 with sigma of 0.02
 C1-C3 \\sim C1-C3A
 with sigma of 0.02
2. Rigid bond restraints
 C9, C8, C7, C4, C1, C2, C6, C5, C3, C6A, C5A, C3A, C2A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
P1 \\sim C4 \\sim C1: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 1.7A
C1 \\sim P1 \\sim C4: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 1.7A
P1: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02 within
1.7A
C2A \\sim C2 \\sim C1 \\sim C3 \\sim C3A \\sim C6A \\sim C6 \\sim C5A \\sim C5
\\sim C4: within 1.7A with sigma of 0.007 and sigma for terminal atoms of 0.001
within 1.7A
Uanis(P1) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.001
Uanis(P1) \\sim Ueq, Uanis(O1) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(P1) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C4) \\sim Ueq: with sigma of
0.1 and sigma for terminal atoms of 0.2
Uanis(C3) = Uanis(C1) = Uanis(C2A) = Uanis(C3A) = Uanis(C2) = Uanis(C6A) =
Uanis(C6) = Uanis(C5) = Uanis(C5A) = Uanis(C4)
Uanis(C2A) = Uanis(C2) = Uanis(C1) = Uanis(C3A) = Uanis(C3) = Uanis(C5A) =
Uanis(C4) = Uanis(C6A) = Uanis(C5)
4. Rigid body (RIGU) restrains
 C2, C5, C3, C6
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C6A, C3A, C2A, C5A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
5. Others
 Sof(C6A)=0.5*(1-FVAR(2))
 Sof(C6)=0.5*FVAR(2)
 Sof(C3A)=Sof(C2A)=1-FVAR(2)
 Sof(C2)=Sof(C3)=FVAR(2)
 Fixed Sof: C5(0.25) C5A(0.25)
;
_atom_sites_solution_hydrogens   .
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.750000 0.11280(2) 1.07988(2) 0.05211(7) Uani 1 2 d DS T P . .
P1 P 0.750000 0.25796(6) 0.89009(4) 0.1043(2) Uani 1 2 d DS TU P A .
C9 C 1.12011(12) 0.07112(10) 1.04764(9) 0.0621(3) Uani 1 1 d . . . . .
N5 N 1.250000 0.03741(13) 1.01747(11) 0.0759(5) Uani 1 2 d S T P . .
N4 N 0.99989(13) 0.09406(10) 1.06778(8) 0.0796(4) Uani 1 1 d . . . . .
O1 O 0.750000 0.18770(12) 0.96279(8) 0.0886(5) Uani 1 2 d DS TU P . .
N1 N 0.750000 0.01544(14) 1.18966(13) 0.0990(6) Uani 1 2 d S T P . .
N3 N 0.750000 0.24661(14) 1.15299(11) 0.0942(6) Uani 1 2 d S T P . .
C8 C 0.750000 -0.0364(2) 1.2467(2) 0.1157(10) Uani 1 2 d S T P . .
N2 N 0.750000 -0.0812(2) 1.32124(19) 0.210(2) Uani 1 2 d S T P . .
C7 C 0.750000 0.3256(2) 1.17126(15) 0.1102(9) Uani 1 2 d S T P . .
C4 C 0.750000 0.1925(3) 0.7887(3) 0.19788(8) Uani 1 2 d DS TU P . .
C1 C 0.9281(4) 0.3231(2) 0.8884(2) 0.19788(8) Uani 1 1 d D U . . .
C2 C 1.0171(8) 0.3279(5) 0.9769(3) 0.19788(8) Uani 0.537(3) 1 d D U P A 1
C6 C 0.750000 0.2117(15) 0.6868(5) 0.19788(8) Uani 0.228(10) 2 d DS TU P B 1
C5 C 0.7977(16) 0.0888(5) 0.7839(7) 0.19788(8) Uani 0.25 1 d D U P B 1
C3 C 0.9377(10) 0.4010(4) 0.8278(4) 0.19788(8) Uani 0.537(3) 1 d D U P A 1
C6A C 0.6961(10) 0.2554(6) 0.7070(3) 0.19788(8) Uani 0.386(5) 1 d D U P B 2
C5A C 0.8972(8) 0.1329(7) 0.7815(9) 0.19788(8) Uani 0.25 1 d D U P B 2
C3A C 1.0597(6) 0.2523(4) 0.8735(4) 0.19788(8) Uani 0.463(3) 1 d D U P A 2
C2A C 0.9520(7) 0.3832(4) 0.9727(3) 0.19788(8) Uani 0.463(3) 1 d D U P A 2


_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 N5 2.5678(17) 5_757 ?
Mn1 N4 2.2057(12) . ?
Mn1 N4 2.2057(12) 7_755 ?
Mn1 O1 2.0838(13) . ?
Mn1 N1 2.1660(19) . ?
Mn1 N3 2.1713(19) . ?
P1 O1 1.4857(15) . ?
P1 C4 1.808(4) . ?
P1 C1 1.799(4) . ?
P1 C1 1.799(4) 7_755 ?
C9 N5 1.3122(14) . ?
C9 N4 1.1402(16) . ?
N1 C8 1.137(3) . ?
N3 C7 1.131(3) . ?
C8 N2 1.307(4) . ?
N2 C7 1.297(4) 6_558 ?
C4 C6 1.596(9) . ?
C4 C5 1.500(9) 7_755 ?
C4 C5 1.500(9) . ?
C4 C6A 1.603(7) 7_755 ?
C4 C6A 1.603(7) . ?
C4 C5A 1.532(7) 7_755 ?
C4 C5A 1.532(7) . ?
C1 C2 1.573(6) . ?
C1 C3 1.431(6) . ?
C1 C3A 1.528(6) . ?
C1 C2A 1.560(5) . ?
C5 C5 0.83(3) 7_755 ?
C6A C6A 0.942(17) 7_755 ?

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 N5 81.66(3) 7_755 5_757 ?
N4 Mn1 N5 81.66(3) . 5_757 ?
N4 Mn1 N4 163.32(7) . 7_755 ?
O1 Mn1 N5 84.09(6) . 5_757 ?
O1 Mn1 N4 89.16(3) . . ?
O1 Mn1 N4 89.16(3) . 7_755 ?
O1 Mn1 N1 171.34(7) . . ?
O1 Mn1 N3 91.41(6) . . ?
N1 Mn1 N5 87.25(7) . 5_757 ?
N1 Mn1 N4 89.58(3) . . ?
N1 Mn1 N4 89.58(4) . 7_755 ?
N1 Mn1 N3 97.25(7) . . ?
N3 Mn1 N5 175.50(6) . 5_757 ?
N3 Mn1 N4 98.32(3) . 7_755 ?
N3 Mn1 N4 98.32(4) . . ?
O1 P1 C4 108.91(16) . . ?
O1 P1 C1 109.90(10) . . ?
O1 P1 C1 109.90(10) . 7_755 ?
C1 P1 C4 103.83(12) . . ?
C1 P1 C4 103.83(12) 7_755 . ?
C1 P1 C1 119.7(2) . 7_755 ?
N4 C9 N5 172.78(15) . . ?
C9 N5 Mn1 119.76(9) 7_855 5_757 ?
C9 N5 Mn1 119.76(9) . 5_757 ?
C9 N5 C9 119.65(17) 7_855 . ?
C9 N4 Mn1 165.24(12) . . ?
P1 O1 Mn1 168.92(10) . . ?
C8 N1 Mn1 179.3(2) . . ?
C7 N3 Mn1 163.13(18) . . ?
N1 C8 N2 169.2(3) . . ?
C7 N2 C8 123.5(3) 6_558 . ?
N3 C7 N2 170.7(3) . 6_568 ?
C6 C4 P1 140.3(8) . . ?
C6 C4 C6A 30.0(6) . 7_755 ?
C5 C4 P1 121.6(5) . . ?
C5 C4 P1 121.6(5) 7_755 . ?
C5 C4 C6 96.4(9) 7_755 . ?
C5 C4 C6 96.4(9) . . ?
C5 C4 C5 32.3(11) 7_755 . ?
C5 C4 C6A 113.6(6) . 7_755 ?
C5 C4 C6A 124.3(6) 7_755 7_755 ?
C5 C4 C5A 73.3(7) . 7_755 ?
C5 C4 C5A 41.1(6) 7_755 7_755 ?
C6A C4 P1 114.0(4) . . ?
C6A C4 P1 114.0(4) 7_755 . ?
C5A C4 P1 109.5(5) . . ?
C5A C4 P1 109.5(5) 7_755 . ?
C5A C4 C6A 89.4(6) 7_755 . ?
C5A C4 C6A 118.8(6) . . ?
C5A C4 C5A 114.1(7) . 7_755 ?
C2 C1 P1 115.8(3) . . ?
C3 C1 P1 116.1(4) . . ?
C3 C1 C2 120.4(4) . . ?
C3A C1 P1 109.3(3) . . ?
C3A C1 C2A 111.6(4) . . ?
C2A C1 P1 111.8(3) . . ?
C5 C5 C4 73.9(5) 7_755 . ?
C6A C6A C4 72.9(3) 7_755 . ?

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
P1 C4 C5 C5 100.3(4) . . . 7_755 ?
P1 C4 C6A C6A 97.9(2) . . . 7_755 ?
O1 P1 C4 C6 180.000(4) . . . . ?
O1 P1 C4 C5 -19.0(6) . . . . ?
O1 P1 C4 C5 19.0(6) . . . 7_755 ?
O1 P1 C4 C6A 161.2(3) . . . . ?
O1 P1 C4 C6A -161.2(3) . . . 7_755 ?
O1 P1 C4 C5A 62.9(5) . . . 7_755 ?
O1 P1 C4 C5A -62.9(5) . . . . ?
O1 P1 C1 C2 -23.5(4) . . . . ?
O1 P1 C1 C3 -173.1(3) . . . . ?
O1 P1 C1 C3A 61.8(3) . . . . ?
O1 P1 C1 C2A -62.3(3) . . . . ?
N1 C8 N2 C7 180.000(6) . . . 6_558 ?
C4 P1 O1 Mn1 180.000(2) . . . . ?
C4 P1 C1 C2 -139.9(4) . . . . ?
C4 P1 C1 C3 70.5(4) . . . . ?
C4 P1 C1 C3A -54.6(3) . . . . ?
C4 P1 C1 C2A -178.6(3) . . . . ?
C1 P1 O1 Mn1 66.87(11) . . . . ?
C1 P1 O1 Mn1 -66.87(11) 7_755 . . . ?
C1 P1 C4 C6 62.94(11) 7_755 . . . ?
C1 P1 C4 C6 -62.94(11) . . . . ?
C1 P1 C4 C5 -98.0(6) 7_755 . . 7_755 ?
C1 P1 C4 C5 98.0(6) . . . . ?
C1 P1 C4 C5 136.1(6) . . . 7_755 ?
C1 P1 C4 C5 -136.1(6) 7_755 . . . ?
C1 P1 C4 C6A -44.2(4) . . . 7_755 ?
C1 P1 C4 C6A 81.7(4) 7_755 . . 7_755 ?
C1 P1 C4 C6A -81.7(4) . . . . ?
C1 P1 C4 C6A 44.2(4) 7_755 . . . ?
C1 P1 C4 C5A -179.9(5) 7_755 . . . ?
C1 P1 C4 C5A 179.9(5) . . . 7_755 ?
C1 P1 C4 C5A -54.2(5) 7_755 . . 7_755 ?
C1 P1 C4 C5A 54.2(5) . . . . ?
C1 P1 C1 C2 105.0(4) 7_755 . . . ?
C1 P1 C1 C3 -44.6(4) 7_755 . . . ?
C1 P1 C1 C3A -169.7(2) 7_755 . . . ?
C1 P1 C1 C2A 66.3(3) 7_755 . . . ?
C6 C4 C5 C5 -91.8(3) . . . 7_755 ?
C5A C4 C6A C6A -33.6(5) . . . 7_755 ?
C5A C4 C6A C6A -151.0(5) 7_755 . . 7_755 ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT242_new                 
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         P1 Check 
RESPONSE: Due to the high temperature of the single crystal diffraction
experiment, the "MainMol" Ueq of the P atom is relatively low compared to
the surrounding atoms due to the presence of disorder in the C atoms around
the P atom and the relatively high "MainMol" Ueq of the C atom.
;
# end Validation Reply Form
