# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_Complex_5'
_database_code_depnum_ccdc_archive 'CCDC 1938926'
loop_
_audit_author_name
_audit_author_address
'Gregory Leitus'
;Chemical Research Support department, Weizmann Institute of Science
Israel
;
_audit_update_record             
;
2019-08-27 deposited with the CCDC.	2019-09-04 downloaded from the CCDC.
;
# Crystallography: Gregory Leitus

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H36 Mn N2 O4 P'
_chemical_formula_sum            'C22 H36 Mn N2 O4 P'
_chemical_formula_weight         478.44

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   12.713(3)
_cell_length_b                   14.096(3)
_cell_length_c                   13.603(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.34(3)
_cell_angle_gamma                90
_cell_volume                     2381.3(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    61998
_cell_measurement_theta_min      2.1876
_cell_measurement_theta_max      26.8074

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.651
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   'Bruker KappaApex2'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker KappaApex CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            60055
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.272
_diffrn_reflns_theta_max         27.170
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5257
_reflns_number_gt                4333
_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       'Software Bruker KappaApex CCD'
_computing_cell_refinement       'Software Bruker KappaApex CCD'
_computing_data_reduction        'Software Bruker KappaApex CCD'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    "Mercury 3.7'"
_computing_publication_material  'SHELXL-2016/4 (Sheldrick, 2016)'
_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)+(0.0357P)²+0.9343P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5257
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0725
_refine_ls_wR_factor_gt          0.0681
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.37589(2) 0.75050(2) 0.56641(2) 0.00904(7) Uani 1 1 d . . . . .
P1 P 0.19622(3) 0.73422(3) 0.57179(3) 0.00989(9) Uani 1 1 d . . . . .
O1 O 0.32590(10) 0.90250(8) 0.41626(9) 0.0216(3) Uani 1 1 d . . . . .
O2 O 0.42881(9) 0.89951(8) 0.72067(9) 0.0231(3) Uani 1 1 d . . . . .
O3 O 0.42252(8) 0.63575(7) 0.65573(8) 0.0123(2) Uani 1 1 d . . . . .
O4 O 0.50705(10) 0.57876(8) 0.80494(8) 0.0220(3) Uani 1 1 d . . . . .
N1 N 0.33061(10) 0.66095(8) 0.44775(9) 0.0103(3) Uani 1 1 d . . . . .
N2 N 0.53504(10) 0.72379(9) 0.52666(10) 0.0126(3) Uani 1 1 d . . . . .
C1 C 0.14496(12) 0.70842(11) 0.43633(11) 0.0136(3) Uani 1 1 d . . . . .
H1A H 0.0770 0.6719 0.4272 0.016 Uiso 1 1 calc R U . . .
H1B H 0.1298 0.7686 0.3984 0.016 Uiso 1 1 calc R U . . .
C2 C 0.22753(13) 0.65212(10) 0.39680(11) 0.0126(3) Uani 1 1 d . . . . .
C3 C 0.20163(14) 0.59419(11) 0.31205(12) 0.0170(3) Uani 1 1 d . . . . .
H3 H 0.1287 0.5861 0.2781 0.020 Uiso 1 1 calc R U . . .
C4 C 0.28344(14) 0.54854(11) 0.27776(12) 0.0195(4) Uani 1 1 d . . . . .
H4 H 0.2670 0.5092 0.2198 0.023 Uiso 1 1 calc R U . . .
C5 C 0.38938(14) 0.56052(11) 0.32843(12) 0.0166(3) Uani 1 1 d . . . . .
H5 H 0.4465 0.5313 0.3047 0.020 Uiso 1 1 calc R U . . .
C6 C 0.41020(13) 0.61607(10) 0.41455(11) 0.0124(3) Uani 1 1 d . . . . .
C7 C 0.52001(12) 0.62717(10) 0.48032(12) 0.0131(3) Uani 1 1 d . . . . .
H7A H 0.5305 0.5787 0.5342 0.016 Uiso 1 1 calc R U . . .
H7B H 0.5750 0.6165 0.4398 0.016 Uiso 1 1 calc R U . . .
C8 C 0.15281(13) 0.62382(11) 0.63393(12) 0.0148(3) Uani 1 1 d . . . . .
C9 C 0.19365(13) 0.53632(11) 0.58545(12) 0.0166(3) Uani 1 1 d . . . . .
H9A H 0.1792 0.4789 0.6211 0.025 Uiso 1 1 calc R U . . .
H9B H 0.2713 0.5423 0.5898 0.025 Uiso 1 1 calc R U . . .
H9C H 0.1564 0.5321 0.5146 0.025 Uiso 1 1 calc R U . . .
C10 C 0.03016(13) 0.61338(12) 0.62076(14) 0.0234(4) Uani 1 1 d . . . . .
H10A H -0.0044 0.6211 0.5496 0.035 Uiso 1 1 calc R U . . .
H10B H 0.0033 0.6620 0.6606 0.035 Uiso 1 1 calc R U . . .
H10C H 0.0134 0.5503 0.6437 0.035 Uiso 1 1 calc R U . . .
C11 C 0.20327(14) 0.62171(12) 0.74740(12) 0.0180(3) Uani 1 1 d . . . . .
H11A H 0.1826 0.6791 0.7792 0.027 Uiso 1 1 calc R U . . .
H11B H 0.2819 0.6190 0.7574 0.027 Uiso 1 1 calc R U . . .
H11C H 0.1775 0.5657 0.7778 0.027 Uiso 1 1 calc R U . . .
C12 C 0.11429(13) 0.83988(11) 0.59817(12) 0.0143(3) Uani 1 1 d . . . . .
C13 C 0.15871(13) 0.93030(11) 0.55849(12) 0.0161(3) Uani 1 1 d . . . . .
H13A H 0.1510 0.9254 0.4854 0.024 Uiso 1 1 calc R U . . .
H13B H 0.2350 0.9376 0.5905 0.024 Uiso 1 1 calc R U . . .
H13C H 0.1184 0.9855 0.5742 0.024 Uiso 1 1 calc R U . . .
C14 C -0.00553(13) 0.83498(12) 0.54730(14) 0.0210(4) Uani 1 1 d . . . . .
H14A H -0.0424 0.8914 0.5652 0.031 Uiso 1 1 calc R U . . .
H14B H -0.0375 0.7780 0.5701 0.031 Uiso 1 1 calc R U . . .
H14C H -0.0132 0.8325 0.4741 0.031 Uiso 1 1 calc R U . . .
C15 C 0.12743(14) 0.85105(12) 0.71252(12) 0.0208(4) Uani 1 1 d . . . . .
H15A H 0.1000 0.9132 0.7273 0.031 Uiso 1 1 calc R U . . .
H15B H 0.2038 0.8461 0.7451 0.031 Uiso 1 1 calc R U . . .
H15C H 0.0869 0.8010 0.7380 0.031 Uiso 1 1 calc R U . . .
C16 C 0.55963(14) 0.79037(11) 0.44905(13) 0.0179(3) Uani 1 1 d . . . . .
H16A H 0.4959 0.7944 0.3928 0.021 Uiso 1 1 calc R U . . .
H16B H 0.6198 0.7639 0.4219 0.021 Uiso 1 1 calc R U . . .
C17 C 0.58973(15) 0.89002(12) 0.48837(14) 0.0244(4) Uani 1 1 d . . . . .
H17A H 0.5409 0.9102 0.5312 0.037 Uiso 1 1 calc R U . . .
H17B H 0.5837 0.9339 0.4315 0.037 Uiso 1 1 calc R U . . .
H17C H 0.6639 0.8901 0.5277 0.037 Uiso 1 1 calc R U . . .
C18 C 0.62684(13) 0.72061(12) 0.61614(13) 0.0190(3) Uani 1 1 d . . . . .
H18A H 0.6092 0.6738 0.6644 0.023 Uiso 1 1 calc R U . . .
H18B H 0.6324 0.7835 0.6493 0.023 Uiso 1 1 calc R U . . .
C19 C 0.73734(14) 0.69532(14) 0.59584(15) 0.0274(4) Uani 1 1 d . . . . .
H19A H 0.7337 0.6330 0.5633 0.041 Uiso 1 1 calc R U . . .
H19B H 0.7906 0.6935 0.6596 0.041 Uiso 1 1 calc R U . . .
H19C H 0.7585 0.7432 0.5516 0.041 Uiso 1 1 calc R U . . .
C20 C 0.34414(12) 0.84419(11) 0.47822(12) 0.0137(3) Uani 1 1 d . . . . .
C21 C 0.41010(12) 0.83742(11) 0.66246(12) 0.0144(3) Uani 1 1 d . . . . .
C22 C 0.46080(13) 0.64140(12) 0.74992(12) 0.0153(3) Uani 1 1 d . . . . .
H22 H 0.4524(16) 0.7063(14) 0.7819(14) 0.026(5) 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 C20 1.7718(16) . ?
Mn1 C21 1.7761(16) . ?
Mn1 N1 2.0329(13) . ?
Mn1 O3 2.0338(11) . ?
Mn1 N2 2.2350(14) . ?
Mn1 P1 2.3122(6) . ?
P1 C1 1.8545(16) . ?
P1 C12 1.8951(16) . ?
P1 C8 1.9079(16) . ?
O1 C20 1.1646(19) . ?
O2 C21 1.1701(19) . ?
O3 C22 1.2721(19) . ?
O4 C22 1.2236(19) . ?
N1 C6 1.350(2) . ?
N1 C2 1.351(2) . ?
N2 C16 1.495(2) . ?
N2 C7 1.4958(19) . ?
N2 C18 1.496(2) . ?
C1 C2 1.504(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.394(2) . ?
C3 C4 1.386(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.497(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C10 1.538(2) . ?
C8 C9 1.540(2) . ?
C8 C11 1.540(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C14 1.534(2) . ?
C12 C15 1.537(2) . ?
C12 C13 1.538(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.523(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.530(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C22 H22 1.03(2) . ?

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
C20 Mn1 C21 88.19(7) . . ?
C20 Mn1 N1 86.58(6) . . ?
C21 Mn1 N1 174.66(6) . . ?
C20 Mn1 O3 172.96(6) . . ?
C21 Mn1 O3 96.60(6) . . ?
N1 Mn1 O3 88.71(5) . . ?
C20 Mn1 N2 92.80(6) . . ?
C21 Mn1 N2 101.66(6) . . ?
N1 Mn1 N2 79.67(5) . . ?
O3 Mn1 N2 81.21(5) . . ?
C20 Mn1 P1 90.68(6) . . ?
C21 Mn1 P1 97.67(6) . . ?
N1 Mn1 P1 81.35(4) . . ?
O3 Mn1 P1 93.78(4) . . ?
N2 Mn1 P1 160.45(4) . . ?
C1 P1 C12 104.57(7) . . ?
C1 P1 C8 101.93(7) . . ?
C12 P1 C8 109.54(7) . . ?
C1 P1 Mn1 97.34(6) . . ?
C12 P1 Mn1 120.97(5) . . ?
C8 P1 Mn1 118.44(5) . . ?
C22 O3 Mn1 123.50(10) . . ?
C6 N1 C2 119.95(13) . . ?
C6 N1 Mn1 116.82(10) . . ?
C2 N1 Mn1 122.93(10) . . ?
C16 N2 C7 107.52(12) . . ?
C16 N2 C18 110.42(13) . . ?
C7 N2 C18 108.83(12) . . ?
C16 N2 Mn1 113.70(10) . . ?
C7 N2 Mn1 102.39(9) . . ?
C18 N2 Mn1 113.41(10) . . ?
C2 C1 P1 109.56(10) . . ?
C2 C1 H1A 109.8 . . ?
P1 C1 H1A 109.8 . . ?
C2 C1 H1B 109.8 . . ?
P1 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
N1 C2 C3 120.68(15) . . ?
N1 C2 C1 116.26(13) . . ?
C3 C2 C1 123.05(14) . . ?
C4 C3 C2 119.26(15) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 119.70(15) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 118.60(15) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
N1 C6 C5 121.72(15) . . ?
N1 C6 C7 114.90(13) . . ?
C5 C6 C7 123.31(14) . . ?
N2 C7 C6 111.47(12) . . ?
N2 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
N2 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C10 C8 C9 107.44(13) . . ?
C10 C8 C11 108.03(14) . . ?
C9 C8 C11 107.91(13) . . ?
C10 C8 P1 114.11(11) . . ?
C9 C8 P1 107.92(11) . . ?
C11 C8 P1 111.21(11) . . ?
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 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C14 C12 C15 110.11(14) . . ?
C14 C12 C13 106.42(13) . . ?
C15 C12 C13 107.56(13) . . ?
C14 C12 P1 114.34(11) . . ?
C15 C12 P1 109.09(11) . . ?
C13 C12 P1 109.09(10) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 C17 113.94(14) . . ?
N2 C16 H16A 108.8 . . ?
C17 C16 H16A 108.8 . . ?
N2 C16 H16B 108.8 . . ?
C17 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 C19 116.53(14) . . ?
N2 C18 H18A 108.2 . . ?
C19 C18 H18A 108.2 . . ?
N2 C18 H18B 108.2 . . ?
C19 C18 H18B 108.2 . . ?
H18A C18 H18B 107.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 C20 Mn1 175.89(14) . . ?
O2 C21 Mn1 175.03(14) . . ?
O4 C22 O3 126.96(15) . . ?
O4 C22 H22 117.6(11) . . ?
O3 C22 H22 115.4(11) . . ?

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
C12 P1 C1 C2 159.10(10) . . . . ?
C8 P1 C1 C2 -86.82(11) . . . . ?
Mn1 P1 C1 C2 34.38(11) . . . . ?
C6 N1 C2 C3 2.4(2) . . . . ?
Mn1 N1 C2 C3 175.92(11) . . . . ?
C6 N1 C2 C1 -177.07(13) . . . . ?
Mn1 N1 C2 C1 -3.54(18) . . . . ?
P1 C1 C2 N1 -23.92(16) . . . . ?
P1 C1 C2 C3 156.63(13) . . . . ?
N1 C2 C3 C4 -2.7(2) . . . . ?
C1 C2 C3 C4 176.73(14) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C3 C4 C5 C6 2.0(2) . . . . ?
C2 N1 C6 C5 0.1(2) . . . . ?
Mn1 N1 C6 C5 -173.77(11) . . . . ?
C2 N1 C6 C7 -176.91(13) . . . . ?
Mn1 N1 C6 C7 9.17(16) . . . . ?
C4 C5 C6 N1 -2.3(2) . . . . ?
C4 C5 C6 C7 174.48(14) . . . . ?
C16 N2 C7 C6 -79.77(15) . . . . ?
C18 N2 C7 C6 160.61(13) . . . . ?
Mn1 N2 C7 C6 40.29(13) . . . . ?
N1 C6 C7 N2 -35.85(18) . . . . ?
C5 C6 C7 N2 147.14(14) . . . . ?
C1 P1 C12 C14 41.06(13) . . . . ?
C8 P1 C12 C14 -67.54(13) . . . . ?
Mn1 P1 C12 C14 149.11(10) . . . . ?
C1 P1 C12 C15 164.83(11) . . . . ?
C8 P1 C12 C15 56.23(13) . . . . ?
Mn1 P1 C12 C15 -87.12(12) . . . . ?
C1 P1 C12 C13 -77.94(12) . . . . ?
C8 P1 C12 C13 173.46(10) . . . . ?
Mn1 P1 C12 C13 30.11(13) . . . . ?
C7 N2 C16 C17 -173.42(14) . . . . ?
C18 N2 C16 C17 -54.81(18) . . . . ?
Mn1 N2 C16 C17 73.98(16) . . . . ?
C16 N2 C18 C19 -55.44(18) . . . . ?
C7 N2 C18 C19 62.36(18) . . . . ?
Mn1 N2 C18 C19 175.61(12) . . . . ?
Mn1 O3 C22 O4 -166.54(13) . . . . ?

_refine_diff_density_max         0.368
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_Complex_3
_database_code_depnum_ccdc_archive 'CCDC 1938928'
loop_
_audit_author_name
_audit_author_address
'Gregory Leitus'
;Chemical Research Support department, Weizmann Institute of Science
Israel
;
_audit_update_record             
;
2019-08-27 deposited with the CCDC.	2019-09-04 downloaded from the CCDC.
;
# Crystallography: Gregory Leitus

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C22 H34 Mn N2 O4 P), C7 H8'
_chemical_formula_sum            'C51 H76 Mn2 N4 O8 P2'
_chemical_formula_weight         1044.97

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      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                   18.0388(14)
_cell_length_b                   10.3918(9)
_cell_length_c                   14.3680(12)
_cell_angle_alpha                90
_cell_angle_beta                 105.838(2)
_cell_angle_gamma                90
_cell_volume                     2591.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13085
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      28.79

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             1108
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.605
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.831
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   'Bruker KappaApex CCD'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker KappaApex CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17621
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.859
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5243
_reflns_number_gt                4082
_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       'Software Bruker KappaApex CCD'
_computing_cell_refinement       'Software Bruker KappaApex CCD'
_computing_data_reduction        'Software Bruker KappaApex CCD'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    "Mercury 3.7'"
_computing_publication_material  'SHELXL-2016/4 (Sheldrick, 2016)'
_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)+(0.0273P)²+0.7574P] 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         5243
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0797
_refine_ls_wR_factor_gt          0.0718
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
Mn1 Mn 0.28599(2) 0.53565(3) 0.15642(2) 0.01396(9) Uani 1 1 d . . . . .
P1 P 0.35001(3) 0.69611(5) 0.10129(4) 0.01421(13) Uani 1 1 d . . . . .
O1 O 0.40610(8) 0.52055(14) 0.34234(11) 0.0248(4) Uani 1 1 d . . . . .
O2 O 0.35308(9) 0.31656(13) 0.07975(11) 0.0271(4) Uani 1 1 d . . . . .
O3 O 0.21032(8) 0.65064(12) 0.20536(10) 0.0176(3) Uani 1 1 d . . . . .
O4 O 0.09277(8) 0.57761(14) 0.20893(11) 0.0235(4) Uani 1 1 d . . . . .
N1 N 0.21154(9) 0.55149(14) 0.02109(12) 0.0149(4) Uani 1 1 d . . . . .
N2 N 0.18884(9) 0.43815(15) 0.17788(12) 0.0158(4) Uani 1 1 d . . . . .
C1 C 0.13832(12) 0.39493(18) 0.08306(15) 0.0199(5) Uani 1 1 d . . . . .
H1A H 0.0841 0.3925 0.0860 0.024 Uiso 1 1 calc R U . . .
H1B H 0.1532 0.3068 0.0690 0.024 Uiso 1 1 calc R U . . .
C2 C 0.14502(12) 0.48420(18) 0.00344(15) 0.0174(5) Uani 1 1 d . . . . .
C3 C 0.08881(12) 0.49283(19) -0.08394(16) 0.0210(5) Uani 1 1 d . . . . .
H3 H 0.0418 0.4468 -0.0942 0.025 Uiso 1 1 calc R U . . .
C4 C 0.10255(12) 0.5700(2) -0.15605(16) 0.0231(5) Uani 1 1 d . . . . .
H4 H 0.0645 0.5783 -0.2162 0.028 Uiso 1 1 calc R U . . .
C5 C 0.17206(12) 0.63500(19) -0.14021(15) 0.0206(5) Uani 1 1 d . . . . .
H5 H 0.1823 0.6870 -0.1897 0.025 Uiso 1 1 calc R U . . .
C6 C 0.22650(12) 0.62319(18) -0.05115(15) 0.0165(4) Uani 1 1 d . . . . .
C7 C 0.30588(11) 0.68059(19) -0.03053(14) 0.0173(5) Uani 1 1 d . . . . .
H7A H 0.3027 0.7665 -0.0612 0.021 Uiso 1 1 calc R U . . .
H7B H 0.3387 0.6252 -0.0589 0.021 Uiso 1 1 calc R U . . .
C8 C 0.19239(12) 0.33757(19) 0.25791(16) 0.0209(5) Uani 1 1 d . . . . .
C9 C 0.25069(13) 0.2345(2) 0.25058(17) 0.0275(5) Uani 1 1 d . . . . .
H9A H 0.2501 0.1653 0.2967 0.041 Uiso 1 1 calc R U . . .
H9B H 0.3023 0.2726 0.2656 0.041 Uiso 1 1 calc R U . . .
H9C H 0.2372 0.1994 0.1848 0.041 Uiso 1 1 calc R U . . .
C10 C 0.21851(12) 0.4043(2) 0.35657(15) 0.0242(5) Uani 1 1 d . . . . .
H10A H 0.1778 0.4624 0.3644 0.036 Uiso 1 1 calc R U . . .
H10B H 0.2655 0.4539 0.3604 0.036 Uiso 1 1 calc R U . . .
H10C H 0.2290 0.3394 0.4080 0.036 Uiso 1 1 calc R U . . .
C11 C 0.11339(12) 0.2751(2) 0.24812(17) 0.0267(5) Uani 1 1 d . . . . .
H11A H 0.1003 0.2191 0.1911 0.040 Uiso 1 1 calc R U . . .
H11B H 0.0742 0.3424 0.2409 0.040 Uiso 1 1 calc R U . . .
H11C H 0.1154 0.2240 0.3061 0.040 Uiso 1 1 calc R U . . .
C12 C 0.45691(11) 0.68720(18) 0.11373(15) 0.0170(4) Uani 1 1 d . . . . .
C13 C 0.47820(12) 0.54431(19) 0.11038(16) 0.0213(5) Uani 1 1 d . . . . .
H13A H 0.5329 0.5368 0.1129 0.032 Uiso 1 1 calc R U . . .
H13B H 0.4468 0.5057 0.0503 0.032 Uiso 1 1 calc R U . . .
H13C H 0.4685 0.4993 0.1658 0.032 Uiso 1 1 calc R U . . .
C14 C 0.48173(12) 0.7567(2) 0.03255(15) 0.0221(5) Uani 1 1 d . . . . .
H14A H 0.4704 0.8488 0.0343 0.033 Uiso 1 1 calc R U . . .
H14B H 0.4534 0.7210 -0.0302 0.033 Uiso 1 1 calc R U . . .
H14C H 0.5372 0.7446 0.0419 0.033 Uiso 1 1 calc R U . . .
C15 C 0.50292(12) 0.7387(2) 0.21294(15) 0.0229(5) Uani 1 1 d . . . . .
H15A H 0.4846 0.6973 0.2639 0.034 Uiso 1 1 calc R U . . .
H15B H 0.4957 0.8320 0.2153 0.034 Uiso 1 1 calc R U . . .
H15C H 0.5577 0.7196 0.2229 0.034 Uiso 1 1 calc R U . . .
C16 C 0.32465(11) 0.86640(18) 0.12896(15) 0.0166(4) Uani 1 1 d . . . . .
C17 C 0.23814(12) 0.88429(19) 0.08029(15) 0.0212(5) Uani 1 1 d . . . . .
H17A H 0.2092 0.8147 0.1004 0.032 Uiso 1 1 calc R U . . .
H17B H 0.2289 0.8823 0.0098 0.032 Uiso 1 1 calc R U . . .
H17C H 0.2212 0.9673 0.0996 0.032 Uiso 1 1 calc R U . . .
C18 C 0.33806(12) 0.87695(19) 0.23872(15) 0.0200(5) Uani 1 1 d . . . . .
H18A H 0.3213 0.9618 0.2547 0.030 Uiso 1 1 calc R U . . .
H18B H 0.3930 0.8658 0.2710 0.030 Uiso 1 1 calc R U . . .
H18C H 0.3085 0.8100 0.2607 0.030 Uiso 1 1 calc R U . . .
C19 C 0.36829(12) 0.97351(18) 0.09241(16) 0.0228(5) Uani 1 1 d . . . . .
H19A H 0.3629 0.9612 0.0233 0.034 Uiso 1 1 calc R U . . .
H19B H 0.4230 0.9704 0.1281 0.034 Uiso 1 1 calc R U . . .
H19C H 0.3469 1.0573 0.1026 0.034 Uiso 1 1 calc R U . . .
C20 C 0.35649(12) 0.52594(18) 0.27057(15) 0.0166(4) Uani 1 1 d . . . . .
C21 C 0.32992(12) 0.40651(19) 0.11121(15) 0.0185(5) Uani 1 1 d . . . . .
C22 C 0.15806(12) 0.56662(19) 0.20086(15) 0.0184(5) Uani 1 1 d . . . . .
C23 C 0.9571(4) 0.3025(5) 0.4975(5) 0.0401(7) Uani 0.5 1 d . . P A -1
H23A H 0.9409 0.2716 0.4306 0.060 Uiso 0.5 1 calc R U P A -1
H23B H 0.9132 0.3000 0.5254 0.060 Uiso 0.5 1 calc R U P A -1
H23C H 0.9984 0.2474 0.5355 0.060 Uiso 0.5 1 calc R U P A -1
C24 C 0.9857(2) 0.4373(3) 0.4992(3) 0.0331(13) Uani 0.5 1 d G . P A -1
C25 C 1.0170(2) 0.4813(3) 0.4268(2) 0.029(8) Uani 0.5 1 d G . P A -1
H25 H 1.0198 0.4257 0.3753 0.034 Uiso 0.5 1 calc R U P A -1
C26 C 1.0444(2) 0.6067(4) 0.4296(2) 0.0365(13) Uani 0.5 1 d G . P A -1
H26 H 1.0658 0.6368 0.3801 0.044 Uiso 0.5 1 calc R U P A -1
C27 C 1.0404(2) 0.6881(3) 0.5049(3) 0.0401(7) Uani 0.5 1 d G . P A -1
H27 H 1.0590 0.7738 0.5068 0.048 Uiso 0.5 1 calc R U P A -1
C28 C 1.0090(2) 0.6441(3) 0.5773(2) 0.0261(10) Uani 0.5 1 d G . P A -1
H28 H 1.0063 0.6997 0.6287 0.031 Uiso 0.5 1 calc R U P A -1
C29 C 0.9817(2) 0.5187(3) 0.5744(3) 0.033(8) Uani 0.5 1 d G . P A -1
H29 H 0.9603 0.4886 0.6239 0.040 Uiso 0.5 1 calc R U P A -1


_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 C21 1.770(2) . ?
Mn1 C20 1.783(2) . ?
Mn1 N1 2.0460(16) . ?
Mn1 O3 2.0760(14) . ?
Mn1 N2 2.1186(16) . ?
Mn1 P1 2.2893(6) . ?
Mn1 C22 2.577(2) . ?
P1 C7 1.850(2) . ?
P1 C12 1.890(2) . ?
P1 C16 1.8968(19) . ?
O1 C20 1.168(2) . ?
O2 C21 1.164(2) . ?
O3 C22 1.274(2) . ?
O4 C22 1.220(2) . ?
N1 C2 1.352(2) . ?
N1 C6 1.363(2) . ?
N2 C1 1.487(2) . ?
N2 C22 1.516(2) . ?
N2 C8 1.542(3) . ?
C1 C2 1.503(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.385(3) . ?
C3 C4 1.385(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.504(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.525(3) . ?
C8 C10 1.532(3) . ?
C8 C11 1.537(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C15 1.537(3) . ?
C12 C13 1.538(3) . ?
C12 C14 1.539(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C18 1.533(3) . ?
C16 C19 1.536(3) . ?
C16 C17 1.537(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C23 C24 1.490(5) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.3900 . ?
C24 C29 1.3900 . ?
C25 C26 1.3900 . ?
C25 H25 0.9500 . ?
C26 C27 1.3900 . ?
C26 H26 0.9500 . ?
C27 C28 1.3900 . ?
C27 H27 0.9500 . ?
C28 C29 1.3900 . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?

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
C21 Mn1 C20 90.94(9) . . ?
C21 Mn1 N1 87.46(8) . . ?
C20 Mn1 N1 175.68(8) . . ?
C21 Mn1 O3 164.27(7) . . ?
C20 Mn1 O3 95.21(7) . . ?
N1 Mn1 O3 87.35(6) . . ?
C21 Mn1 N2 99.31(8) . . ?
C20 Mn1 N2 104.46(8) . . ?
N1 Mn1 N2 79.76(6) . . ?
O3 Mn1 N2 65.13(6) . . ?
C21 Mn1 P1 96.12(7) . . ?
C20 Mn1 P1 93.39(6) . . ?
N1 Mn1 P1 82.81(5) . . ?
O3 Mn1 P1 97.95(4) . . ?
N2 Mn1 P1 156.09(5) . . ?
C21 Mn1 C22 134.96(8) . . ?
C20 Mn1 C22 103.96(8) . . ?
N1 Mn1 C22 79.95(7) . . ?
O3 Mn1 C22 29.32(5) . . ?
N2 Mn1 C22 36.04(6) . . ?
P1 Mn1 C22 124.41(5) . . ?
C7 P1 C12 103.61(9) . . ?
C7 P1 C16 103.58(9) . . ?
C12 P1 C16 108.91(9) . . ?
C7 P1 Mn1 100.02(7) . . ?
C12 P1 Mn1 121.98(6) . . ?
C16 P1 Mn1 115.70(7) . . ?
C22 O3 Mn1 97.71(12) . . ?
C2 N1 C6 119.34(17) . . ?
C2 N1 Mn1 117.10(13) . . ?
C6 N1 Mn1 123.55(13) . . ?
C1 N2 C22 107.23(14) . . ?
C1 N2 C8 111.65(15) . . ?
C22 N2 C8 112.18(15) . . ?
C1 N2 Mn1 109.60(12) . . ?
C22 N2 Mn1 88.69(11) . . ?
C8 N2 Mn1 124.40(12) . . ?
N2 C1 C2 110.77(16) . . ?
N2 C1 H1A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
N1 C2 C3 121.97(19) . . ?
N1 C2 C1 115.35(18) . . ?
C3 C2 C1 122.61(18) . . ?
C2 C3 C4 118.7(2) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 119.2(2) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
N1 C6 C5 120.82(19) . . ?
N1 C6 C7 116.26(17) . . ?
C5 C6 C7 122.81(19) . . ?
C6 C7 P1 110.89(14) . . ?
C6 C7 H7A 109.5 . . ?
P1 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
P1 C7 H7B 109.5 . . ?
H7A C7 H7B 108.0 . . ?
C9 C8 C10 109.76(18) . . ?
C9 C8 C11 109.69(17) . . ?
C10 C8 C11 108.62(18) . . ?
C9 C8 N2 108.28(17) . . ?
C10 C8 N2 108.82(16) . . ?
C11 C8 N2 111.66(17) . . ?
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 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C15 C12 C13 106.80(16) . . ?
C15 C12 C14 110.15(16) . . ?
C13 C12 C14 107.63(17) . . ?
C15 C12 P1 110.46(14) . . ?
C13 C12 P1 107.54(13) . . ?
C14 C12 P1 113.94(14) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C18 C16 C19 110.37(16) . . ?
C18 C16 C17 108.36(17) . . ?
C19 C16 C17 107.95(16) . . ?
C18 C16 P1 107.64(13) . . ?
C19 C16 P1 115.40(14) . . ?
C17 C16 P1 106.88(13) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 C20 Mn1 175.81(18) . . ?
O2 C21 Mn1 174.47(18) . . ?
O4 C22 O3 130.65(19) . . ?
O4 C22 N2 121.56(17) . . ?
O3 C22 N2 107.75(17) . . ?
O4 C22 Mn1 171.24(16) . . ?
O3 C22 Mn1 52.97(10) . . ?
N2 C22 Mn1 55.28(9) . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C29 120.0 . . ?
C25 C24 C23 120.5(4) . . ?
C29 C24 C23 119.5(4) . . ?
C26 C25 C24 120.0 . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 120.0 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 C28 120.0 . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C29 C28 C27 120.0 . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C24 120.0 . . ?
C28 C29 H29 120.0 . . ?
C24 C29 H29 120.0 . . ?

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
C22 N2 C1 C2 65.4(2) . . . . ?
C8 N2 C1 C2 -171.39(16) . . . . ?
Mn1 N2 C1 C2 -29.52(19) . . . . ?
C6 N1 C2 C3 -4.7(3) . . . . ?
Mn1 N1 C2 C3 176.70(15) . . . . ?
C6 N1 C2 C1 172.37(17) . . . . ?
Mn1 N1 C2 C1 -6.3(2) . . . . ?
N2 C1 C2 N1 24.2(2) . . . . ?
N2 C1 C2 C3 -158.76(18) . . . . ?
N1 C2 C3 C4 1.9(3) . . . . ?
C1 C2 C3 C4 -174.88(19) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C2 N1 C6 C5 4.5(3) . . . . ?
Mn1 N1 C6 C5 -176.96(14) . . . . ?
C2 N1 C6 C7 -171.90(17) . . . . ?
Mn1 N1 C6 C7 6.6(2) . . . . ?
C4 C5 C6 N1 -1.7(3) . . . . ?
C4 C5 C6 C7 174.49(18) . . . . ?
N1 C6 C7 P1 -23.2(2) . . . . ?
C5 C6 C7 P1 160.49(16) . . . . ?
C12 P1 C7 C6 152.76(13) . . . . ?
C16 P1 C7 C6 -93.56(14) . . . . ?
Mn1 P1 C7 C6 26.16(14) . . . . ?
C1 N2 C8 C9 81.6(2) . . . . ?
C22 N2 C8 C9 -158.03(16) . . . . ?
Mn1 N2 C8 C9 -53.6(2) . . . . ?
C1 N2 C8 C10 -159.17(16) . . . . ?
C22 N2 C8 C10 -38.8(2) . . . . ?
Mn1 N2 C8 C10 65.7(2) . . . . ?
C1 N2 C8 C11 -39.3(2) . . . . ?
C22 N2 C8 C11 81.1(2) . . . . ?
Mn1 N2 C8 C11 -174.46(13) . . . . ?
C7 P1 C12 C15 162.86(14) . . . . ?
C16 P1 C12 C15 53.08(16) . . . . ?
Mn1 P1 C12 C15 -85.90(14) . . . . ?
C7 P1 C12 C13 -80.95(15) . . . . ?
C16 P1 C12 C13 169.27(14) . . . . ?
Mn1 P1 C12 C13 30.29(16) . . . . ?
C7 P1 C12 C14 38.25(16) . . . . ?
C16 P1 C12 C14 -71.53(16) . . . . ?
Mn1 P1 C12 C14 149.49(12) . . . . ?
C7 P1 C16 C18 164.18(13) . . . . ?
C12 P1 C16 C18 -86.03(15) . . . . ?
Mn1 P1 C16 C18 55.82(15) . . . . ?
C7 P1 C16 C19 -72.09(16) . . . . ?
C12 P1 C16 C19 37.71(17) . . . . ?
Mn1 P1 C16 C19 179.55(12) . . . . ?
C7 P1 C16 C17 47.95(16) . . . . ?
C12 P1 C16 C17 157.75(14) . . . . ?
Mn1 P1 C16 C17 -60.41(15) . . . . ?
Mn1 O3 C22 O4 -169.7(2) . . . . ?
Mn1 O3 C22 N2 7.82(15) . . . . ?
C1 N2 C22 O4 60.1(2) . . . . ?
C8 N2 C22 O4 -62.8(2) . . . . ?
Mn1 N2 C22 O4 170.23(18) . . . . ?
C1 N2 C22 O3 -117.73(17) . . . . ?
C8 N2 C22 O3 119.34(18) . . . . ?
Mn1 N2 C22 O3 -7.60(15) . . . . ?
C1 N2 C22 Mn1 -110.14(14) . . . . ?
C8 N2 C22 Mn1 126.94(15) . . . . ?
C29 C24 C25 C26 0.0 . . . . ?
C23 C24 C25 C26 -179.2(5) . . . . ?
C24 C25 C26 C27 0.0 . . . . ?
C25 C26 C27 C28 0.0 . . . . ?
C26 C27 C28 C29 0.0 . . . . ?
C27 C28 C29 C24 0.0 . . . . ?
C25 C24 C29 C28 0.0 . . . . ?
C23 C24 C29 C28 179.2(5) . . . . ?

_refine_diff_density_max         0.348
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_Complex_4'
_database_code_depnum_ccdc_archive 'CCDC 1938929'
loop_
_audit_author_name
_audit_author_address
'Gregory Leitus'
;Chemical Research Support department, Weizmann Institute of Science
Israel
;
_audit_update_record             
;
2019-08-27 deposited with the CCDC.	2019-09-04 downloaded from the CCDC.
;
# Linda JW Shimon
# Noel Angel Espinosa Jalapa, David Milstein
# revised for Amit Kumar

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H36 Mn N2 O2 P'
_chemical_formula_sum            'C21 H36 Mn N2 O2 P'
_chemical_formula_weight         434.43

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   12.5824(8)
_cell_length_b                   14.2411(7)
_cell_length_c                   13.1504(8)
_cell_angle_alpha                90
_cell_angle_beta                 107.519(7)
_cell_angle_gamma                90
_cell_volume                     2247.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8881
_cell_measurement_theta_min      3.6620
_cell_measurement_theta_max      32.9220

_exptl_crystal_description       prism
_exptl_crystal_colour            red-orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.676
_shelx_estimated_absorpt_T_min   0.877
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.61832
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.4c (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Rigaku XtaLabPro Kappa Dual'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28603
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.471
_diffrn_reflns_theta_max         30.504
_diffrn_reflns_theta_full        26.000
_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 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6835
_reflns_number_gt                5272
_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       'CrysAlisPro 1.171.39.4c (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.4c (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.4c (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    "Mercury 3.7'"
_computing_publication_material  'SHELXL-2016/4 (Sheldrick, 2016)'
_refine_special_details          
;  CO group is disordered over two positions, the hydride was not found but
placed in calculated position and held fixed during refinement.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0581P)²+1.6015P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6835
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1212
_refine_ls_wR_factor_gt          0.1103
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
MN1 Mn 0.55133(2) 0.72996(2) 0.36219(2) 0.01606(8) Uani 1 1 d . . . . .
P1 P 0.55107(4) 0.71841(3) 0.19124(3) 0.01528(10) Uani 1 1 d . . . . .
N1 N 0.41891(13) 0.64201(11) 0.31147(13) 0.0202(3) Uani 1 1 d . . . . .
N2 N 0.49644(14) 0.72196(11) 0.50415(13) 0.0222(3) Uani 1 1 d . . . . .
O1 O 0.70358(13) 0.89123(10) 0.41239(12) 0.0279(3) Uani 1 1 d . . . . .
C1 C 0.40551(15) 0.67829(13) 0.12853(14) 0.0198(3) Uani 1 1 d . . . . .
H1A H 0.356669 0.733281 0.102823 0.024 Uiso 1 1 calc R U . . .
H1B H 0.402222 0.637807 0.066462 0.024 Uiso 1 1 calc R U . . .
C2 C 0.36515(16) 0.62455(13) 0.20760(15) 0.0215(4) Uani 1 1 d . . . . .
C3 C 0.27492(18) 0.56279(15) 0.17712(17) 0.0287(4) Uani 1 1 d . . . . .
H3 H 0.240469 0.549106 0.103866 0.034 Uiso 1 1 calc R U . . .
C4 C 0.23605(19) 0.52166(16) 0.25442(19) 0.0348(5) Uani 1 1 d . . . . .
H4 H 0.174896 0.479326 0.234943 0.042 Uiso 1 1 calc R U . . .
C5 C 0.28765(18) 0.54315(16) 0.36073(18) 0.0317(5) Uani 1 1 d . . . . .
H5 H 0.260358 0.517927 0.414934 0.038 Uiso 1 1 calc R U . . .
C6 C 0.38039(16) 0.60247(13) 0.38689(16) 0.0234(4) Uani 1 1 d . . . . .
C7 C 0.44967(18) 0.62484(14) 0.49835(16) 0.0250(4) Uani 1 1 d . . . . .
H7A H 0.403289 0.619717 0.547010 0.030 Uiso 1 1 calc R U . . .
H7B H 0.511363 0.578968 0.521706 0.030 Uiso 1 1 calc R U . . .
C8 C 0.63587(16) 0.62020(13) 0.15521(15) 0.0209(4) Uani 1 1 d . . . . .
C9 C 0.62236(19) 0.60998(15) 0.03551(16) 0.0289(4) Uani 1 1 d . . . . .
H9A H 0.658870 0.662858 0.011909 0.043 Uiso 1 1 calc R U . . .
H9B H 0.542924 0.609525 -0.004702 0.043 Uiso 1 1 calc R U . . .
H9C H 0.656672 0.551028 0.023073 0.043 Uiso 1 1 calc R U . . .
C10 C 0.59487(18) 0.52759(13) 0.19171(17) 0.0265(4) Uani 1 1 d . . . . .
H10A H 0.517018 0.516669 0.150109 0.040 Uiso 1 1 calc R U . . .
H10B H 0.600630 0.531920 0.267554 0.040 Uiso 1 1 calc R U . . .
H10C H 0.640951 0.475418 0.180617 0.040 Uiso 1 1 calc R U . . .
C11 C 0.76076(16) 0.63178(15) 0.21549(16) 0.0253(4) Uani 1 1 d . . . . .
H11A H 0.802225 0.578308 0.199689 0.038 Uiso 1 1 calc R U . . .
H11B H 0.771160 0.634347 0.292345 0.038 Uiso 1 1 calc R U . . .
H11C H 0.788326 0.690038 0.192757 0.038 Uiso 1 1 calc R U . . .
C12 C 0.55803(16) 0.82651(13) 0.10880(14) 0.0209(4) Uani 1 1 d . . . . .
C13 C 0.50050(19) 0.81432(15) -0.01124(16) 0.0277(4) Uani 1 1 d . . . . .
H13A H 0.422319 0.796959 -0.023212 0.042 Uiso 1 1 calc R U . . .
H13B H 0.538181 0.764764 -0.039014 0.042 Uiso 1 1 calc R U . . .
H13C H 0.504296 0.873450 -0.048111 0.042 Uiso 1 1 calc R U . . .
C14 C 0.68077(18) 0.85521(15) 0.12836(18) 0.0299(4) Uani 1 1 d . . . . .
H14A H 0.717597 0.809254 0.094829 0.045 Uiso 1 1 calc R U . . .
H14B H 0.718813 0.857218 0.205226 0.045 Uiso 1 1 calc R U . . .
H14C H 0.683892 0.917384 0.097449 0.045 Uiso 1 1 calc R U . . .
C15 C 0.49921(19) 0.90819(13) 0.14657(16) 0.0273(4) Uani 1 1 d . . . . .
H15A H 0.501096 0.964206 0.103862 0.041 Uiso 1 1 calc R U . . .
H15B H 0.537478 0.921402 0.221853 0.041 Uiso 1 1 calc R U . . .
H15C H 0.421597 0.890968 0.138039 0.041 Uiso 1 1 calc R U . . .
C16 C 0.40435(18) 0.78945(15) 0.50196(18) 0.0287(4) Uani 1 1 d . . . . .
H16A H 0.371235 0.771818 0.558671 0.034 Uiso 1 1 calc R U . . .
H16B H 0.345483 0.783328 0.432673 0.034 Uiso 1 1 calc R U . . .
C17 C 0.4411(2) 0.89167(15) 0.5175(2) 0.0342(5) Uani 1 1 d . . . . .
H17A H 0.492253 0.900220 0.589645 0.051 Uiso 1 1 calc R U . . .
H17B H 0.375733 0.931995 0.507894 0.051 Uiso 1 1 calc R U . . .
H17C H 0.479129 0.908594 0.465101 0.051 Uiso 1 1 calc R U . . .
C18 C 0.59099(18) 0.73118(15) 0.60454(16) 0.0271(4) Uani 1 1 d . . . . .
H18A H 0.625996 0.793386 0.604160 0.033 Uiso 1 1 calc R U . . .
H18B H 0.647437 0.683031 0.603581 0.033 Uiso 1 1 calc R U . . .
C19 C 0.5625(2) 0.7214(2) 0.70925(19) 0.0424(6) Uani 1 1 d . . . . .
H19A H 0.509741 0.770706 0.713611 0.064 Uiso 1 1 calc R U . . .
H19B H 0.630626 0.727367 0.769425 0.064 Uiso 1 1 calc R U . . .
H19C H 0.528779 0.659688 0.711766 0.064 Uiso 1 1 calc R U . . .
C20 C 0.64511(16) 0.82558(13) 0.39512(14) 0.0196(3) Uani 1 1 d . . . . .
C21A C 0.66302(17) 0.64372(16) 0.41998(16) 0.0226(4) Uani 0.926(3) 1 d . . P A
1
H21A H 0.454070 0.804730 0.320560 0.034 Uiso 0.9261 1 d . U P A 1
O2A O 0.73521(15) 0.59940(12) 0.45659(13) 0.0323(4) Uani 0.926(3) 1 d . . P A 1
C21B C 0.426(2) 0.820(2) 0.311(2) 0.0226(4) Uani 0.074(3) 1 d . . P A 2
H21B H 0.647420 0.655810 0.411880 0.034 Uiso 0.0739 1 d . U P A 2
O2B O 0.3666(19) 0.8560(16) 0.2873(16) 0.0323(4) Uani 0.074(3) 1 d . . 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 C20 1.7683(19) . ?
MN1 C21A 1.849(2) . ?
MN1 C21B 1.99(3) . ?
MN1 N1 2.0300(16) . ?
MN1 N2 2.1797(16) . ?
MN1 P1 2.2531(5) . ?
MN1 H21A 1.5899 . ?
MN1 H21B 1.5900 . ?
P1 C1 1.8578(18) . ?
P1 C12 1.9000(18) . ?
P1 C8 1.9035(19) . ?
N1 C6 1.351(2) . ?
N1 C2 1.352(2) . ?
N2 C18 1.493(3) . ?
N2 C7 1.496(2) . ?
N2 C16 1.499(3) . ?
O1 C20 1.169(2) . ?
C1 C2 1.498(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.396(3) . ?
C3 C4 1.384(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.497(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.538(3) . ?
C8 C11 1.541(3) . ?
C8 C10 1.544(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.536(3) . ?
C12 C15 1.539(3) . ?
C12 C14 1.543(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.523(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.530(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C21A O2A 1.092(3) . ?
C21B O2B 0.88(3) . ?

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
C20 MN1 C21A 92.42(9) . . ?
C20 MN1 C21B 89.5(7) . . ?
C20 MN1 N1 167.65(8) . . ?
C21A MN1 N1 99.92(8) . . ?
C21B MN1 N1 78.2(7) . . ?
C20 MN1 N2 100.99(7) . . ?
C21A MN1 N2 90.62(7) . . ?
C21B MN1 N2 84.4(7) . . ?
N1 MN1 N2 78.98(6) . . ?
C20 MN1 P1 95.79(6) . . ?
C21A MN1 P1 97.72(6) . . ?
C21B MN1 P1 86.8(7) . . ?
N1 MN1 P1 82.68(5) . . ?
N2 MN1 P1 160.92(5) . . ?
C20 MN1 H21A 87.5 . . ?
C21A MN1 H21A 176.0 . . ?
N1 MN1 H21A 80.2 . . ?
N2 MN1 H21A 85.4 . . ?
P1 MN1 H21A 86.3 . . ?
C20 MN1 H21B 92.4 . . ?
C21B MN1 H21B 174.9 . . ?
N1 MN1 H21B 99.9 . . ?
N2 MN1 H21B 90.6 . . ?
P1 MN1 H21B 97.7 . . ?
C1 P1 C12 101.80(8) . . ?
C1 P1 C8 102.42(9) . . ?
C12 P1 C8 109.13(8) . . ?
C1 P1 MN1 99.82(6) . . ?
C12 P1 MN1 121.58(6) . . ?
C8 P1 MN1 118.00(6) . . ?
C6 N1 C2 118.95(17) . . ?
C6 N1 MN1 117.15(13) . . ?
C2 N1 MN1 123.84(12) . . ?
C18 N2 C7 108.84(15) . . ?
C18 N2 C16 111.47(16) . . ?
C7 N2 C16 107.58(15) . . ?
C18 N2 MN1 112.27(12) . . ?
C7 N2 MN1 103.06(11) . . ?
C16 N2 MN1 113.10(12) . . ?
C2 C1 P1 110.12(13) . . ?
C2 C1 H1A 109.6 . . ?
P1 C1 H1A 109.6 . . ?
C2 C1 H1B 109.6 . . ?
P1 C1 H1B 109.6 . . ?
H1A C1 H1B 108.2 . . ?
N1 C2 C3 121.47(17) . . ?
N1 C2 C1 115.87(16) . . ?
C3 C2 C1 122.62(18) . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 119.0(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C4 C5 C6 118.98(19) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
N1 C6 C5 121.93(19) . . ?
N1 C6 C7 113.48(17) . . ?
C5 C6 C7 124.53(18) . . ?
N2 C7 C6 110.54(15) . . ?
N2 C7 H7A 109.5 . . ?
C6 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C9 C8 C11 108.54(16) . . ?
C9 C8 C10 107.02(16) . . ?
C11 C8 C10 108.41(16) . . ?
C9 C8 P1 115.26(13) . . ?
C11 C8 P1 110.77(13) . . ?
C10 C8 P1 106.58(13) . . ?
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 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C15 107.07(16) . . ?
C13 C12 C14 109.86(16) . . ?
C15 C12 C14 107.49(16) . . ?
C13 C12 P1 113.99(13) . . ?
C15 C12 P1 108.60(12) . . ?
C14 C12 P1 109.59(13) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 C17 114.12(18) . . ?
N2 C16 H16A 108.7 . . ?
C17 C16 H16A 108.7 . . ?
N2 C16 H16B 108.7 . . ?
C17 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 C19 116.56(18) . . ?
N2 C18 H18A 108.2 . . ?
C19 C18 H18A 108.2 . . ?
N2 C18 H18B 108.2 . . ?
C19 C18 H18B 108.2 . . ?
H18A C18 H18B 107.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 C20 MN1 176.50(17) . . ?
O2A C21A MN1 173.67(19) . . ?
O2B C21B MN1 176(3) . . ?

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
C12 P1 C1 C2 -153.62(13) . . . . ?
C8 P1 C1 C2 93.50(14) . . . . ?
MN1 P1 C1 C2 -28.24(13) . . . . ?
C6 N1 C2 C3 -3.5(3) . . . . ?
MN1 N1 C2 C3 179.51(15) . . . . ?
C6 N1 C2 C1 174.06(16) . . . . ?
MN1 N1 C2 C1 -2.9(2) . . . . ?
P1 C1 C2 N1 22.3(2) . . . . ?
P1 C1 C2 C3 -160.08(16) . . . . ?
N1 C2 C3 C4 3.0(3) . . . . ?
C1 C2 C3 C4 -174.4(2) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 -2.8(3) . . . . ?
C2 N1 C6 C5 0.9(3) . . . . ?
MN1 N1 C6 C5 178.02(16) . . . . ?
C2 N1 C6 C7 178.03(16) . . . . ?
MN1 N1 C6 C7 -4.8(2) . . . . ?
C4 C5 C6 N1 2.3(3) . . . . ?
C4 C5 C6 C7 -174.5(2) . . . . ?
C18 N2 C7 C6 -162.50(16) . . . . ?
C16 N2 C7 C6 76.58(19) . . . . ?
MN1 N2 C7 C6 -43.15(17) . . . . ?
N1 C6 C7 N2 34.2(2) . . . . ?
C5 C6 C7 N2 -148.7(2) . . . . ?
C18 N2 C16 C17 55.5(2) . . . . ?
C7 N2 C16 C17 174.70(18) . . . . ?
MN1 N2 C16 C17 -72.2(2) . . . . ?
C7 N2 C18 C19 -63.5(2) . . . . ?
C16 N2 C18 C19 55.0(2) . . . . ?
MN1 N2 C18 C19 -176.89(16) . . . . ?

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
C3 H3 O1_$1 0.95 2.56 3.387(3) 145.1 4_575
C5 H5 O2A_$2 0.95 2.36 3.224(3) 150.1 3_666
C11 H11B O2A 0.98 2.39 3.314(3) 157.2 .
C15 H15C O2B 0.98 2.32 2.94(2) 119.8 .
C16 H16B O2B 0.99 2.26 2.878(19) 119.5 .

_refine_diff_density_max         0.926
_refine_diff_density_min         -0.684
_refine_diff_density_rms         0.079

####################################################################### 
# 
# 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_Complex_3'
_database_code_depnum_ccdc_archive 'CCDC 1938927'
loop_
_audit_author_name
_audit_author_address
'Gregory Leitus'
;Chemical Research Support department, Weizmann Institute of Science
Israel
;
_audit_update_record             
;
2019-08-27 deposited with the CCDC.	2019-09-04 downloaded from the CCDC.
;
# Crystallography: Gregory Leitus
# start Validation Reply Form
_vrf_THETM01_Complex_3'          
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The crystals were very thin and small plates. Full data could be
collected till resolution 1.05 A with Cu-radiation at 100 K to maximize signal
to noise. Although the data resolution is very low the refinement is stable
and no restraints or constraints have been applied.
;
_vrf_PLAT027_Complex_3'          
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      26.00 Degree
RESPONSE: See above.
;
_vrf_PLAT088_Complex_3'          
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.43 Note  
RESPONSE: See response on Alerts level A
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H34 Mn N2 O4 P'
_chemical_formula_sum            'C22 H34 Mn N2 O4 P'
_chemical_formula_weight         476.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.0332(4)
_cell_length_b                   11.6911(4)
_cell_length_c                   17.3894(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.460(4)
_cell_angle_gamma                90
_cell_volume                     2228.82(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4464
_cell_measurement_theta_min      4.5380
_cell_measurement_theta_max      47.7800

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.033
_exptl_crystal_size_min          0.023
_exptl_absorpt_coefficient_mu    5.750
_shelx_estimated_absorpt_T_min   0.846
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.73032
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8651
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.032
_diffrn_reflns_theta_max         47.964
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2073
_reflns_number_gt                1884
_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       'CrysAlisPro 1.171.39.4c (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.4c (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.4c (Rigaku OD, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    "Mercury 3.7'"
_computing_publication_material  'SHELXL-2016/4 (Sheldrick, 2016)'
_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)+(0.0291P)²+2.2266P] 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         2073
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0268
_refine_ls_wR_factor_ref         0.0670
_refine_ls_wR_factor_gt          0.0655
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
Mn1 Mn 0.69546(4) 0.79175(4) 0.64316(3) 0.01504(19) Uani 1 1 d . . . . .
P1 P 0.87716(7) 0.71452(6) 0.62060(5) 0.0151(2) Uani 1 1 d . . . . .
O1 O 0.7639(2) 1.0231(2) 0.60012(13) 0.0281(6) Uani 1 1 d . . . . .
O2 O 0.75333(19) 0.86725(19) 0.80393(15) 0.0296(6) Uani 1 1 d . . . . .
O3 O 0.66484(17) 0.62649(17) 0.68213(11) 0.0156(5) Uani 1 1 d . . . . .
O4 O 0.71576(18) 0.44191(19) 0.67012(11) 0.0196(5) Uani 1 1 d . . . . .
N1 N 0.6416(2) 0.7113(2) 0.54313(14) 0.0139(6) Uani 1 1 d . . . . .
N2 N 0.5020(2) 0.8320(2) 0.62526(14) 0.0159(6) Uani 1 1 d . . . . .
C1 C 0.4792(3) 0.8418(3) 0.53874(17) 0.0195(8) Uani 1 1 d . . . . .
H1A H 0.3903 0.8429 0.5223 0.023 Uiso 1 1 calc R U . . .
H1B H 0.5146 0.9140 0.5216 0.023 Uiso 1 1 calc R U . . .
C2 C 0.5361(3) 0.7424(3) 0.50270(18) 0.0154(8) Uani 1 1 d . . . . .
C3 C 0.4891(3) 0.6830(3) 0.43813(18) 0.0175(8) Uani 1 1 d . . . . .
H3 H 0.4148 0.7063 0.4095 0.021 Uiso 1 1 calc R U . . .
C4 C 0.5517(3) 0.5887(3) 0.41552(18) 0.0192(8) Uani 1 1 d . . . . .
H4 H 0.5229 0.5486 0.3696 0.023 Uiso 1 1 calc R U . . .
C5 C 0.6567(3) 0.5529(3) 0.46016(17) 0.0165(8) Uani 1 1 d . . . . .
H5 H 0.6989 0.4866 0.4463 0.020 Uiso 1 1 calc R U . . .
C6 C 0.6989(3) 0.6149(3) 0.52499(17) 0.0140(8) Uani 1 1 d . . . . .
C7 C 0.7968(3) 0.5802(2) 0.58742(17) 0.0158(8) Uani 1 1 d . . . . .
H7 H 0.8521 0.5190 0.5715 0.019 Uiso 1 1 calc R U . . .
C8 C 0.4227(3) 0.7383(3) 0.64979(17) 0.0181(8) Uani 1 1 d . . . . .
H8A H 0.4481 0.6653 0.6277 0.022 Uiso 1 1 calc R U . . .
H8B H 0.3374 0.7534 0.6279 0.022 Uiso 1 1 calc R U . . .
C9 C 0.4263(3) 0.7248(3) 0.73606(17) 0.0204(8) Uani 1 1 d . . . . .
H9A H 0.3835 0.6545 0.7476 0.031 Uiso 1 1 calc R U . . .
H9B H 0.3864 0.7907 0.7574 0.031 Uiso 1 1 calc R U . . .
H9C H 0.5113 0.7206 0.7593 0.031 Uiso 1 1 calc R U . . .
C10 C 0.4725(3) 0.9437(2) 0.66075(18) 0.0193(8) Uani 1 1 d . . . . .
H10A H 0.5269 1.0029 0.6426 0.023 Uiso 1 1 calc R U . . .
H10B H 0.4922 0.9372 0.7175 0.023 Uiso 1 1 calc R U . . .
C11 C 0.3425(3) 0.9854(3) 0.64432(19) 0.0236(9) Uani 1 1 d . . . . .
H11A H 0.3204 0.9909 0.5883 0.035 Uiso 1 1 calc R U . . .
H11B H 0.3351 1.0609 0.6678 0.035 Uiso 1 1 calc R U . . .
H11C H 0.2876 0.9315 0.6662 0.035 Uiso 1 1 calc R U . . .
C12 C 0.9541(3) 0.7628(3) 0.53362(18) 0.0187(8) Uani 1 1 d . . . . .
C13 C 1.0524(3) 0.8515(3) 0.55807(19) 0.0244(9) Uani 1 1 d . . . . .
H13A H 1.0176 0.9129 0.5870 0.037 Uiso 1 1 calc R U . . .
H13B H 1.0834 0.8834 0.5120 0.037 Uiso 1 1 calc R U . . .
H13C H 1.1195 0.8150 0.5909 0.037 Uiso 1 1 calc R U . . .
C14 C 0.8628(3) 0.8193(3) 0.47274(17) 0.0214(8) Uani 1 1 d . . . . .
H14A H 0.8030 0.7624 0.4513 0.032 Uiso 1 1 calc R U . . .
H14B H 0.9061 0.8503 0.4312 0.032 Uiso 1 1 calc R U . . .
H14C H 0.8206 0.8814 0.4967 0.032 Uiso 1 1 calc R U . . .
C15 C 1.0113(3) 0.6626(3) 0.49311(19) 0.0251(8) Uani 1 1 d . . . . .
H15A H 1.0695 0.6225 0.5304 0.038 Uiso 1 1 calc R U . . .
H15B H 1.0538 0.6921 0.4507 0.038 Uiso 1 1 calc R U . . .
H15C H 0.9471 0.6095 0.4724 0.038 Uiso 1 1 calc R U . . .
C16 C 0.9961(3) 0.6754(3) 0.70292(18) 0.0174(8) Uani 1 1 d . . . . .
C17 C 0.9344(3) 0.6079(3) 0.76282(18) 0.0213(8) Uani 1 1 d . . . . .
H17A H 0.8627 0.6500 0.7759 0.032 Uiso 1 1 calc R U . . .
H17B H 0.9918 0.5975 0.8095 0.032 Uiso 1 1 calc R U . . .
H17C H 0.9090 0.5330 0.7415 0.032 Uiso 1 1 calc R U . . .
C18 C 1.1007(3) 0.6029(3) 0.67938(19) 0.0237(8) Uani 1 1 d . . . . .
H18A H 1.0677 0.5347 0.6517 0.036 Uiso 1 1 calc R U . . .
H18B H 1.1538 0.5797 0.7257 0.036 Uiso 1 1 calc R U . . .
H18C H 1.1479 0.6477 0.6456 0.036 Uiso 1 1 calc R U . . .
C19 C 1.0465(3) 0.7851(3) 0.74286(19) 0.0233(8) Uani 1 1 d . . . . .
H19A H 1.0905 0.8293 0.7070 0.035 Uiso 1 1 calc R U . . .
H19B H 1.1022 0.7652 0.7888 0.035 Uiso 1 1 calc R U . . .
H19C H 0.9789 0.8309 0.7583 0.035 Uiso 1 1 calc R U . . .
C20 C 0.7339(3) 0.9302(3) 0.61451(18) 0.0189(8) Uani 1 1 d . . . . .
C21 C 0.7313(3) 0.8375(3) 0.7398(2) 0.0185(8) Uani 1 1 d . . . . .
C22 C 0.7210(3) 0.5439(3) 0.65319(18) 0.0166(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 C20 1.759(4) . ?
Mn1 C21 1.765(4) . ?
Mn1 N1 2.008(2) . ?
Mn1 O3 2.088(2) . ?
Mn1 N2 2.174(2) . ?
Mn1 P1 2.2727(9) . ?
P1 C7 1.863(3) . ?
P1 C16 1.886(3) . ?
P1 C12 1.901(3) . ?
O1 C20 1.170(4) . ?
O2 C21 1.168(4) . ?
O3 C22 1.281(4) . ?
O4 C22 1.231(4) . ?
N1 C2 1.340(4) . ?
N1 C6 1.347(4) . ?
N2 C8 1.494(4) . ?
N2 C10 1.496(4) . ?
N2 C1 1.501(4) . ?
C1 C2 1.493(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.371(4) . ?
C3 C4 1.381(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.377(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.499(4) . ?
C7 C22 1.551(4) . ?
C7 H7 1.0000 . ?
C8 C9 1.504(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.511(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C14 1.527(4) . ?
C12 C13 1.526(4) . ?
C12 C15 1.538(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C18 1.525(4) . ?
C16 C17 1.527(4) . ?
C16 C19 1.532(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C20 Mn1 C21 87.44(14) . . ?
C20 Mn1 N1 104.07(12) . . ?
C21 Mn1 N1 168.34(12) . . ?
C20 Mn1 O3 175.10(11) . . ?
C21 Mn1 O3 89.92(12) . . ?
N1 Mn1 O3 78.74(9) . . ?
C20 Mn1 N2 91.41(12) . . ?
C21 Mn1 N2 100.47(12) . . ?
N1 Mn1 N2 77.72(9) . . ?
O3 Mn1 N2 93.13(8) . . ?
C20 Mn1 P1 94.07(10) . . ?
C21 Mn1 P1 100.21(10) . . ?
N1 Mn1 P1 81.09(8) . . ?
O3 Mn1 P1 82.32(6) . . ?
N2 Mn1 P1 158.81(7) . . ?
C7 P1 C16 107.27(13) . . ?
C7 P1 C12 104.07(14) . . ?
C16 P1 C12 109.94(14) . . ?
C7 P1 Mn1 89.43(10) . . ?
C16 P1 Mn1 121.16(10) . . ?
C12 P1 Mn1 120.04(10) . . ?
C22 O3 Mn1 117.87(19) . . ?
C2 N1 C6 120.5(3) . . ?
C2 N1 Mn1 118.8(2) . . ?
C6 N1 Mn1 119.6(2) . . ?
C8 N2 C10 111.2(2) . . ?
C8 N2 C1 107.7(2) . . ?
C10 N2 C1 109.1(2) . . ?
C8 N2 Mn1 113.42(18) . . ?
C10 N2 Mn1 112.68(17) . . ?
C1 N2 Mn1 102.18(17) . . ?
C2 C1 N2 109.3(2) . . ?
C2 C1 H1A 109.8 . . ?
N2 C1 H1A 109.8 . . ?
C2 C1 H1B 109.8 . . ?
N2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.3 . . ?
N1 C2 C3 121.2(3) . . ?
N1 C2 C1 111.9(3) . . ?
C3 C2 C1 126.8(3) . . ?
C2 C3 C4 118.8(3) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 119.0(3) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
N1 C6 C5 120.5(3) . . ?
N1 C6 C7 112.1(3) . . ?
C5 C6 C7 126.9(3) . . ?
C6 C7 C22 101.8(2) . . ?
C6 C7 P1 106.0(2) . . ?
C22 C7 P1 106.3(2) . . ?
C6 C7 H7 113.9 . . ?
C22 C7 H7 113.9 . . ?
P1 C7 H7 113.9 . . ?
N2 C8 C9 114.3(2) . . ?
N2 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
N2 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
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 . . ?
N2 C10 C11 116.7(2) . . ?
N2 C10 H10A 108.1 . . ?
C11 C10 H10A 108.1 . . ?
N2 C10 H10B 108.1 . . ?
C11 C10 H10B 108.1 . . ?
H10A C10 H10B 107.3 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C14 C12 C13 107.0(3) . . ?
C14 C12 C15 106.5(2) . . ?
C13 C12 C15 109.2(3) . . ?
C14 C12 P1 111.2(2) . . ?
C13 C12 P1 110.3(2) . . ?
C15 C12 P1 112.4(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C18 C16 C17 107.8(2) . . ?
C18 C16 C19 109.9(3) . . ?
C17 C16 C19 106.8(3) . . ?
C18 C16 P1 114.5(2) . . ?
C17 C16 P1 108.5(2) . . ?
C19 C16 P1 109.1(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 C20 Mn1 175.6(3) . . ?
O2 C21 Mn1 179.0(3) . . ?
O4 C22 O3 126.8(3) . . ?
O4 C22 C7 119.0(3) . . ?
O3 C22 C7 114.1(3) . . ?

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
C8 N2 C1 C2 -72.9(3) . . . . ?
C10 N2 C1 C2 166.3(2) . . . . ?
Mn1 N2 C1 C2 46.8(2) . . . . ?
C6 N1 C2 C3 -5.6(4) . . . . ?
Mn1 N1 C2 C3 -173.5(2) . . . . ?
C6 N1 C2 C1 172.0(3) . . . . ?
Mn1 N1 C2 C1 4.1(3) . . . . ?
N2 C1 C2 N1 -36.2(3) . . . . ?
N2 C1 C2 C3 141.2(3) . . . . ?
N1 C2 C3 C4 0.8(4) . . . . ?
C1 C2 C3 C4 -176.4(3) . . . . ?
C2 C3 C4 C5 3.1(4) . . . . ?
C3 C4 C5 C6 -2.3(4) . . . . ?
C2 N1 C6 C5 6.4(4) . . . . ?
Mn1 N1 C6 C5 174.2(2) . . . . ?
C2 N1 C6 C7 -166.0(3) . . . . ?
Mn1 N1 C6 C7 1.7(3) . . . . ?
C4 C5 C6 N1 -2.4(4) . . . . ?
C4 C5 C6 C7 168.8(3) . . . . ?
N1 C6 C7 C22 68.9(3) . . . . ?
C5 C6 C7 C22 -103.0(3) . . . . ?
N1 C6 C7 P1 -42.1(3) . . . . ?
C5 C6 C7 P1 146.1(3) . . . . ?
C16 P1 C7 C6 177.14(19) . . . . ?
C12 P1 C7 C6 -66.4(2) . . . . ?
Mn1 P1 C7 C6 54.55(19) . . . . ?
C16 P1 C7 C22 69.4(2) . . . . ?
C12 P1 C7 C22 -174.1(2) . . . . ?
Mn1 P1 C7 C22 -53.18(19) . . . . ?
C10 N2 C8 C9 -55.2(3) . . . . ?
C1 N2 C8 C9 -174.6(2) . . . . ?
Mn1 N2 C8 C9 73.0(3) . . . . ?
C8 N2 C10 C11 -57.7(3) . . . . ?
C1 N2 C10 C11 61.0(3) . . . . ?
Mn1 N2 C10 C11 173.7(2) . . . . ?
C7 P1 C16 C18 67.9(2) . . . . ?
C12 P1 C16 C18 -44.6(3) . . . . ?
Mn1 P1 C16 C18 168.07(18) . . . . ?
C7 P1 C16 C17 -52.5(2) . . . . ?
C12 P1 C16 C17 -165.0(2) . . . . ?
Mn1 P1 C16 C17 47.6(2) . . . . ?
C7 P1 C16 C19 -168.5(2) . . . . ?
C12 P1 C16 C19 78.9(2) . . . . ?
Mn1 P1 C16 C19 -68.4(2) . . . . ?
Mn1 O3 C22 O4 178.6(2) . . . . ?
Mn1 O3 C22 C7 -4.7(3) . . . . ?
C6 C7 C22 O4 109.6(3) . . . . ?
P1 C7 C22 O4 -139.7(2) . . . . ?
C6 C7 C22 O3 -67.4(3) . . . . ?
P1 C7 C22 O3 43.3(3) . . . . ?

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.041

