# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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#######################################################################

data_491ZVN14
_database_code_depnum_ccdc_archive 'CCDC 1522570'
_audit_update_record             
;
2016-12-13 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C50 H50 Mn2 O4 P2'
_chemical_formula_sum            'C50 H50 Mn2 O4 P2'
_chemical_formula_weight         886.72

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'
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                   11.3989(3)
_cell_length_b                   16.7647(4)
_cell_length_c                   12.0131(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.0125(10)
_cell_angle_gamma                90
_cell_volume                     2128.34(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9253
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      27.51

_exptl_crystal_description       rhombohedron
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             924
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.444
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.092
_exptl_absorpt_coefficient_mu    0.714
_shelx_estimated_absorpt_T_min   0.742
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7230
_exptl_absorpt_correction_T_max  0.9316
_exptl_absorpt_process_details   '(Sheldrick, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ-geometry diffractometer 208039-01'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            26549
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.195
_diffrn_reflns_theta_max         27.099
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4688
_reflns_number_gt                4146
_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       'APEX2 v2014.1-1(Bruker, 2014)'
_computing_cell_refinement       'APEX2 v2014.1-1(Bruker, 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/1 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'

_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)+(0.0473P)²+1.6533P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4688
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 0.17411(2) 0.42696(2) 0.81784(2) 0.01594(9) Uani 1 1 d . . . . .
P1 P 0.19732(4) 0.48682(2) 0.66405(4) 0.01345(11) Uani 1 1 d . . . . .
O1 O 0.43626(15) 0.37030(12) 0.91430(15) 0.0446(4) Uani 1 1 d . . . . .
O2 O 0.08035(19) 0.28419(10) 0.67218(15) 0.0471(5) Uani 1 1 d . . . . .
C1 C -0.00612(17) 0.46113(11) 0.82359(16) 0.0211(4) Uani 1 1 d . . . . .
C2 C 0.07830(18) 0.52772(11) 0.86100(17) 0.0217(4) Uani 1 1 d . . . . .
C3 C 0.18389(18) 0.50482(11) 0.96502(17) 0.0224(4) Uani 1 1 d . . . . .
C4 C 0.16521(18) 0.42354(11) 0.99267(16) 0.0217(4) Uani 1 1 d . . . . .
C5 C 0.04815(18) 0.39705(11) 0.90668(17) 0.0215(4) Uani 1 1 d . . . . .
C6 C -0.13321(19) 0.46050(14) 0.72630(19) 0.0295(4) Uani 1 1 d . . . . .
H6A H -0.1943 0.4858 0.7549 0.044 Uiso 1 1 calc R U . . .
H6B H -0.1590 0.4053 0.7028 0.044 Uiso 1 1 calc R U . . .
H6C H -0.1304 0.4900 0.6569 0.044 Uiso 1 1 calc R U . . .
C7 C 0.0512(2) 0.60931(12) 0.80611(19) 0.0290(4) Uani 1 1 d . . . . .
H7A H -0.0054 0.6377 0.8370 0.043 Uiso 1 1 calc R U . . .
H7B H 0.0107 0.6045 0.7186 0.043 Uiso 1 1 calc R U . . .
H7C H 0.1306 0.6390 0.8268 0.043 Uiso 1 1 calc R U . . .
C8 C 0.2899(2) 0.55690(14) 1.0413(2) 0.0372(5) Uani 1 1 d . . . . .
H8A H 0.2711 0.5770 1.1094 0.056 Uiso 1 1 calc R U . . .
H8B H 0.2996 0.6019 0.9934 0.056 Uiso 1 1 calc R U . . .
H8C H 0.3685 0.5260 1.0711 0.056 Uiso 1 1 calc R U . . .
C9 C 0.2503(2) 0.37750(13) 1.10008(18) 0.0308(4) Uani 1 1 d . . . . .
H9A H 0.2218 0.3848 1.1669 0.046 Uiso 1 1 calc R U . . .
H9B H 0.3373 0.3970 1.1235 0.046 Uiso 1 1 calc R U . . .
H9C H 0.2472 0.3207 1.0798 0.046 Uiso 1 1 calc R U . . .
C10 C -0.0127(2) 0.31812(12) 0.9067(2) 0.0304(4) Uani 1 1 d . . . . .
H10A H -0.0709 0.3228 0.9491 0.046 Uiso 1 1 calc R U . . .
H10B H 0.0527 0.2785 0.9472 0.046 Uiso 1 1 calc R U . . .
H10C H -0.0597 0.3012 0.8237 0.046 Uiso 1 1 calc R U . . .
C11 C 0.33326(19) 0.39446(12) 0.87382(17) 0.0253(4) Uani 1 1 d . . . . .
C12 C 0.1204(2) 0.34102(11) 0.72799(18) 0.0259(4) Uani 1 1 d . . . . .
C13 C 0.05158(16) 0.49892(10) 0.53979(15) 0.0158(3) Uani 1 1 d . . . . .
C14 C 0.26489(16) 0.58712(10) 0.67527(16) 0.0171(3) Uani 1 1 d . . . . .
C15 C 0.22732(18) 0.64023(11) 0.57877(17) 0.0232(4) Uani 1 1 d . . . . .
H15 H 0.1623 0.6255 0.5050 0.028 Uiso 1 1 calc R U . . .
C16 C 0.2845(2) 0.71437(12) 0.5902(2) 0.0294(4) Uani 1 1 d . . . . .
H16 H 0.2598 0.7497 0.5236 0.035 Uiso 1 1 calc R U . . .
C17 C 0.3774(2) 0.73726(12) 0.6982(2) 0.0307(5) Uani 1 1 d . . . . .
H17 H 0.4156 0.7884 0.7059 0.037 Uiso 1 1 calc R U . . .
C18 C 0.41404(19) 0.68536(12) 0.7942(2) 0.0304(4) Uani 1 1 d . . . . .
H18 H 0.4774 0.7010 0.8684 0.037 Uiso 1 1 calc R U . . .
C19 C 0.35889(18) 0.61020(11) 0.78325(17) 0.0245(4) Uani 1 1 d . . . . .
H19 H 0.3855 0.5746 0.8496 0.029 Uiso 1 1 calc R U . . .
C20 C 0.28733(17) 0.43192(10) 0.58989(16) 0.0173(3) Uani 1 1 d . . . . .
C21 C 0.41445(19) 0.44796(13) 0.6166(2) 0.0288(4) Uani 1 1 d . . . . .
H21 H 0.4556 0.4886 0.6727 0.035 Uiso 1 1 calc R U . . .
C22 C 0.4819(2) 0.40477(15) 0.5615(2) 0.0383(5) Uani 1 1 d . . . . .
H22 H 0.5687 0.4163 0.5798 0.046 Uiso 1 1 calc R U . . .
C23 C 0.4230(2) 0.34495(14) 0.4802(2) 0.0363(5) Uani 1 1 d . . . . .
H23 H 0.4692 0.3156 0.4426 0.044 Uiso 1 1 calc R U . . .
C24 C 0.2973(2) 0.32813(13) 0.45420(19) 0.0320(5) Uani 1 1 d . . . . .
H24 H 0.2568 0.2871 0.3985 0.038 Uiso 1 1 calc R U . . .
C25 C 0.22964(18) 0.37100(11) 0.50912(17) 0.0240(4) Uani 1 1 d . . . . .
H25 H 0.1432 0.3586 0.4914 0.029 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 C12 1.766(2) . ?
Mn1 C11 1.768(2) . ?
Mn1 C4 2.1411(18) . ?
Mn1 C5 2.1450(19) . ?
Mn1 C1 2.1587(18) . ?
Mn1 C3 2.1668(18) . ?
Mn1 C2 2.1771(18) . ?
Mn1 P1 2.2038(5) . ?
P1 C13 1.7805(18) . ?
P1 C14 1.8332(17) . ?
P1 C20 1.8381(18) . ?
O1 C11 1.162(2) . ?
O2 C12 1.156(2) . ?
C1 C2 1.432(3) . ?
C1 C5 1.439(3) . ?
C1 C6 1.482(3) . ?
C2 C3 1.425(3) . ?
C2 C7 1.499(3) . ?
C3 C4 1.437(3) . ?
C3 C8 1.494(3) . ?
C4 C5 1.418(3) . ?
C4 C9 1.504(3) . ?
C5 C10 1.494(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C13 C13 1.206(3) 3_566 ?
C14 C19 1.392(3) . ?
C14 C15 1.396(3) . ?
C15 C16 1.386(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.392(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.388(3) . ?
C20 C25 1.392(3) . ?
C21 C22 1.390(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.385(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.376(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.389(3) . ?
C24 H24 0.9500 . ?
C25 H25 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
C12 Mn1 C11 93.00(10) . . ?
C12 Mn1 C4 116.40(8) . . ?
C11 Mn1 C4 92.16(8) . . ?
C12 Mn1 C5 88.28(8) . . ?
C11 Mn1 C5 121.43(8) . . ?
C4 Mn1 C5 38.65(7) . . ?
C12 Mn1 C1 96.89(9) . . ?
C11 Mn1 C1 157.34(8) . . ?
C4 Mn1 C1 65.18(7) . . ?
C5 Mn1 C1 39.06(7) . . ?
C12 Mn1 C3 152.88(8) . . ?
C11 Mn1 C3 98.26(8) . . ?
C4 Mn1 C3 38.97(7) . . ?
C5 Mn1 C3 64.79(7) . . ?
C1 Mn1 C3 64.69(7) . . ?
C12 Mn1 C2 133.51(9) . . ?
C11 Mn1 C2 133.10(8) . . ?
C4 Mn1 C2 64.83(7) . . ?
C5 Mn1 C2 64.77(7) . . ?
C1 Mn1 C2 38.56(7) . . ?
C3 Mn1 C2 38.29(7) . . ?
C12 Mn1 P1 88.98(6) . . ?
C11 Mn1 P1 91.76(7) . . ?
C4 Mn1 P1 154.05(5) . . ?
C5 Mn1 P1 146.79(5) . . ?
C1 Mn1 P1 108.71(5) . . ?
C3 Mn1 P1 115.09(5) . . ?
C2 Mn1 P1 94.30(5) . . ?
C13 P1 C14 101.04(8) . . ?
C13 P1 C20 99.54(8) . . ?
C14 P1 C20 101.51(8) . . ?
C13 P1 Mn1 112.78(6) . . ?
C14 P1 Mn1 122.35(6) . . ?
C20 P1 Mn1 116.26(6) . . ?
C2 C1 C5 107.51(16) . . ?
C2 C1 C6 126.62(17) . . ?
C5 C1 C6 125.51(18) . . ?
C2 C1 Mn1 71.42(10) . . ?
C5 C1 Mn1 69.95(10) . . ?
C6 C1 Mn1 129.32(13) . . ?
C3 C2 C1 108.22(16) . . ?
C3 C2 C7 126.76(18) . . ?
C1 C2 C7 124.74(18) . . ?
C3 C2 Mn1 70.46(10) . . ?
C1 C2 Mn1 70.02(10) . . ?
C7 C2 Mn1 129.94(13) . . ?
C2 C3 C4 107.97(16) . . ?
C2 C3 C8 127.13(18) . . ?
C4 C3 C8 124.63(18) . . ?
C2 C3 Mn1 71.25(10) . . ?
C4 C3 Mn1 69.55(10) . . ?
C8 C3 Mn1 129.41(15) . . ?
C5 C4 C3 108.00(16) . . ?
C5 C4 C9 126.31(18) . . ?
C3 C4 C9 125.52(18) . . ?
C5 C4 Mn1 70.82(10) . . ?
C3 C4 Mn1 71.48(10) . . ?
C9 C4 Mn1 127.07(14) . . ?
C4 C5 C1 108.29(16) . . ?
C4 C5 C10 125.96(18) . . ?
C1 C5 C10 125.63(18) . . ?
C4 C5 Mn1 70.53(11) . . ?
C1 C5 Mn1 70.98(10) . . ?
C10 C5 Mn1 127.18(14) . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C11 Mn1 176.47(19) . . ?
O2 C12 Mn1 176.15(19) . . ?
C13 C13 P1 173.6(2) 3_566 . ?
C19 C14 C15 119.07(16) . . ?
C19 C14 P1 118.61(14) . . ?
C15 C14 P1 122.30(14) . . ?
C16 C15 C14 120.21(18) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 120.47(19) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 119.59(18) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.52(19) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C14 120.13(18) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
C21 C20 C25 118.85(17) . . ?
C21 C20 P1 121.01(14) . . ?
C25 C20 P1 120.09(14) . . ?
C20 C21 C22 120.3(2) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 120.3(2) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 119.77(19) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 120.2(2) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C20 120.61(19) . . ?
C24 C25 H25 119.7 . . ?
C20 C25 H25 119.7 . . ?

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
C5 C1 C2 C3 0.6(2) . . . . ?
C6 C1 C2 C3 173.96(18) . . . . ?
Mn1 C1 C2 C3 -60.38(13) . . . . ?
C5 C1 C2 C7 -173.64(17) . . . . ?
C6 C1 C2 C7 -0.3(3) . . . . ?
Mn1 C1 C2 C7 125.39(18) . . . . ?
C5 C1 C2 Mn1 60.97(12) . . . . ?
C6 C1 C2 Mn1 -125.67(19) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C7 C2 C3 C4 174.05(18) . . . . ?
Mn1 C2 C3 C4 -60.13(13) . . . . ?
C1 C2 C3 C8 -174.17(19) . . . . ?
C7 C2 C3 C8 -0.1(3) . . . . ?
Mn1 C2 C3 C8 125.7(2) . . . . ?
C1 C2 C3 Mn1 60.10(12) . . . . ?
C7 C2 C3 Mn1 -125.82(19) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C8 C3 C4 C5 173.77(19) . . . . ?
Mn1 C3 C4 C5 -61.76(13) . . . . ?
C2 C3 C4 C9 -175.98(18) . . . . ?
C8 C3 C4 C9 -1.7(3) . . . . ?
Mn1 C3 C4 C9 122.82(19) . . . . ?
C2 C3 C4 Mn1 61.20(13) . . . . ?
C8 C3 C4 Mn1 -124.5(2) . . . . ?
C3 C4 C5 C1 0.9(2) . . . . ?
C9 C4 C5 C1 176.30(18) . . . . ?
Mn1 C4 C5 C1 -61.26(13) . . . . ?
C3 C4 C5 C10 -175.45(18) . . . . ?
C9 C4 C5 C10 -0.1(3) . . . . ?
Mn1 C4 C5 C10 122.37(19) . . . . ?
C3 C4 C5 Mn1 62.19(13) . . . . ?
C9 C4 C5 Mn1 -122.44(19) . . . . ?
C2 C1 C5 C4 -0.9(2) . . . . ?
C6 C1 C5 C4 -174.40(18) . . . . ?
Mn1 C1 C5 C4 60.97(13) . . . . ?
C2 C1 C5 C10 175.45(18) . . . . ?
C6 C1 C5 C10 2.0(3) . . . . ?
Mn1 C1 C5 C10 -122.64(19) . . . . ?
C2 C1 C5 Mn1 -61.91(12) . . . . ?
C6 C1 C5 Mn1 124.63(19) . . . . ?
C13 P1 C14 C19 159.70(15) . . . . ?
C20 P1 C14 C19 -98.07(16) . . . . ?
Mn1 P1 C14 C19 33.50(17) . . . . ?
C13 P1 C14 C15 -21.72(17) . . . . ?
C20 P1 C14 C15 80.52(16) . . . . ?
Mn1 P1 C14 C15 -147.91(13) . . . . ?
C19 C14 C15 C16 1.0(3) . . . . ?
P1 C14 C15 C16 -177.59(15) . . . . ?
C14 C15 C16 C17 -1.5(3) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
C16 C17 C18 C19 0.3(3) . . . . ?
C17 C18 C19 C14 -0.7(3) . . . . ?
C15 C14 C19 C18 0.1(3) . . . . ?
P1 C14 C19 C18 178.74(16) . . . . ?
C13 P1 C20 C21 140.42(16) . . . . ?
C14 P1 C20 C21 36.99(17) . . . . ?
Mn1 P1 C20 C21 -98.20(15) . . . . ?
C13 P1 C20 C25 -42.19(16) . . . . ?
C14 P1 C20 C25 -145.62(15) . . . . ?
Mn1 P1 C20 C25 79.19(15) . . . . ?
C25 C20 C21 C22 1.2(3) . . . . ?
P1 C20 C21 C22 178.66(17) . . . . ?
C20 C21 C22 C23 -0.5(4) . . . . ?
C21 C22 C23 C24 -0.2(4) . . . . ?
C22 C23 C24 C25 0.1(3) . . . . ?
C23 C24 C25 C20 0.7(3) . . . . ?
C21 C20 C25 C24 -1.4(3) . . . . ?
P1 C20 C25 C24 -178.82(15) . . . . ?

_refine_diff_density_max         0.562
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.069

_shelxl_version_number           2014-1


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Benzene'
_chemical_properties_physical    
', Air-sensitive,Moisture-sensitive,Oxygen-sensitive'
####################################################################### 
# 
# 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_444ZVN14
_database_code_depnum_ccdc_archive 'CCDC 1522568'
_audit_update_record             
;
2016-12-13 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H34 Mn2 O4 P2'
_chemical_formula_sum            'C40 H34 Mn2 O4 P2'
_chemical_formula_weight         750.49

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'
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                   11.8159(5)
_cell_length_b                   8.6579(3)
_cell_length_c                   17.7993(8)
_cell_angle_alpha                90
_cell_angle_beta                 107.4395(15)
_cell_angle_gamma                90
_cell_volume                     1737.19(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9986
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      27.49

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             772
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.327
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.142
_exptl_absorpt_coefficient_mu    0.860
_shelx_estimated_absorpt_T_min   0.766
_shelx_estimated_absorpt_T_max   0.888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9212
_exptl_absorpt_correction_T_max  0.9646
_exptl_absorpt_process_details   '(Sheldrick, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ-geometry diffractometer 208039-01'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            22723
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.399
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3818
_reflns_number_gt                3182
_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       'APEX2 v2014.1-1(Bruker, 2014)'
_computing_cell_refinement       'APEX2 v2014.1-1(Bruker, 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/1 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'

_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)+(0.0543P)²+1.5527P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3818
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.66872(3) 0.55678(4) 0.39744(2) 0.02968(13) Uani 1 1 d . . . . .
P1 P 0.81369(5) 0.38505(6) 0.43401(3) 0.02442(14) Uani 1 1 d . . . . .
O1 O 0.6933(3) 0.5771(3) 0.56615(14) 0.0894(10) Uani 1 1 d . . . . .
O2 O 0.4768(2) 0.3286(3) 0.34597(17) 0.0755(8) Uani 1 1 d . . . . .
C1 C 0.5254(3) 0.7243(4) 0.35068(19) 0.0551(8) Uani 1 1 d . . . . .
H1A H 0.4953 0.7348 0.2927 0.066 Uiso 1 1 calc R U . . .
H1B H 0.4626 0.7292 0.3771 0.066 Uiso 1 1 calc R U . . .
C2 C 0.6313(3) 0.7968(3) 0.38807(18) 0.0563(8) Uani 1 1 d . . . . .
H2 H 0.6349 0.8505 0.4385 0.068 Uiso 1 1 calc R U . . .
C3 C 0.7421(3) 0.7697(4) 0.3748(2) 0.0604(9) Uani 1 1 d . . . . .
H3 H 0.8147 0.8078 0.4157 0.072 Uiso 1 1 calc R U . . .
C4 C 0.7584(3) 0.6547(4) 0.3218(2) 0.0608(9) Uani 1 1 d . . . . .
H4 H 0.8418 0.6192 0.3300 0.073 Uiso 1 1 calc R U . . .
C5 C 0.6682(3) 0.5595(4) 0.27403(17) 0.0562(9) Uani 1 1 d . . . . .
H5A H 0.6938 0.4637 0.2534 0.067 Uiso 1 1 calc R U . . .
H5B H 0.6007 0.6121 0.2359 0.067 Uiso 1 1 calc R U . . .
C6 C 0.6806(3) 0.5703(3) 0.50027(17) 0.0487(7) Uani 1 1 d . . . . .
C7 C 0.5532(3) 0.4154(4) 0.36780(17) 0.0460(7) Uani 1 1 d . . . . .
C8 C 0.9548(2) 0.4663(3) 0.48400(13) 0.0299(5) Uani 1 1 d . . . . .
C9 C 0.84771(19) 0.2806(3) 0.35375(12) 0.0262(4) Uani 1 1 d . . . . .
C10 C 0.7707(2) 0.1634(3) 0.31617(13) 0.0317(5) Uani 1 1 d . . . . .
H10 H 0.7092 0.1301 0.3366 0.038 Uiso 1 1 calc R U . . .
C11 C 0.7841(3) 0.0951(3) 0.24849(14) 0.0409(6) Uani 1 1 d . . . . .
H11 H 0.7321 0.0146 0.2230 0.049 Uiso 1 1 calc R U . . .
C12 C 0.8727(3) 0.1441(3) 0.21860(14) 0.0450(7) Uani 1 1 d . . . . .
H12 H 0.8802 0.0989 0.1717 0.054 Uiso 1 1 calc R U . . .
C13 C 0.9507(3) 0.2583(3) 0.25615(15) 0.0439(6) Uani 1 1 d . . . . .
H13 H 1.0126 0.2901 0.2357 0.053 Uiso 1 1 calc R U . . .
C14 C 0.9385(2) 0.3266(3) 0.32392(14) 0.0355(5) Uani 1 1 d . . . . .
H14 H 0.9923 0.4049 0.3500 0.043 Uiso 1 1 calc R U . . .
C15 C 0.8066(2) 0.2271(3) 0.50120(12) 0.0293(5) Uani 1 1 d . . . . .
C16 C 0.7019(2) 0.1900(3) 0.51774(15) 0.0380(6) Uani 1 1 d . . . . .
H16 H 0.6327 0.2505 0.4961 0.046 Uiso 1 1 calc R U . . .
C17 C 0.6986(3) 0.0641(3) 0.56609(17) 0.0469(7) Uani 1 1 d . . . . .
H17 H 0.6267 0.0380 0.5767 0.056 Uiso 1 1 calc R U . . .
C18 C 0.7995(3) -0.0226(3) 0.59852(15) 0.0473(7) Uani 1 1 d . . . . .
H18 H 0.7971 -0.1075 0.6318 0.057 Uiso 1 1 calc R U . . .
C19 C 0.9032(3) 0.0136(3) 0.58273(15) 0.0460(7) Uani 1 1 d . . . . .
H19 H 0.9723 -0.0466 0.6050 0.055 Uiso 1 1 calc R U . . .
C20 C 0.9076(2) 0.1377(3) 0.53443(14) 0.0385(6) Uani 1 1 d . . . . .
H20 H 0.9797 0.1621 0.5239 0.046 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 C7 1.791(3) . ?
Mn1 C6 1.797(3) . ?
Mn1 C2 2.121(3) . ?
Mn1 C4 2.124(3) . ?
Mn1 C3 2.127(3) . ?
Mn1 C5 2.195(3) . ?
Mn1 C1 2.195(3) . ?
Mn1 P1 2.2136(6) . ?
P1 C8 1.782(2) . ?
P1 C9 1.834(2) . ?
P1 C15 1.835(2) . ?
O1 C6 1.138(4) . ?
O2 C7 1.149(4) . ?
C1 C2 1.380(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.418(5) . ?
C2 H2 1.0000 . ?
C3 C4 1.424(5) . ?
C3 H3 1.0000 . ?
C4 C5 1.413(5) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C8 C8 1.201(5) 3_766 ?
C9 C14 1.390(3) . ?
C9 C10 1.393(3) . ?
C10 C11 1.393(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.375(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.392(4) . ?
C15 C20 1.396(3) . ?
C16 C17 1.397(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.373(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.387(4) . ?
C19 H19 0.9500 . ?
C20 H20 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
C7 Mn1 C6 99.46(15) . . ?
C7 Mn1 C2 121.59(13) . . ?
C6 Mn1 C2 88.11(12) . . ?
C7 Mn1 C4 124.55(15) . . ?
C6 Mn1 C4 135.93(16) . . ?
C2 Mn1 C4 72.00(14) . . ?
C7 Mn1 C3 148.70(14) . . ?
C6 Mn1 C3 103.01(14) . . ?
C2 Mn1 C3 39.01(14) . . ?
C4 Mn1 C3 39.14(14) . . ?
C7 Mn1 C5 86.51(14) . . ?
C6 Mn1 C5 174.03(15) . . ?
C2 Mn1 C5 88.44(12) . . ?
C4 Mn1 C5 38.15(14) . . ?
C3 Mn1 C5 71.33(14) . . ?
C7 Mn1 C1 84.62(14) . . ?
C6 Mn1 C1 99.13(13) . . ?
C2 Mn1 C1 37.24(13) . . ?
C4 Mn1 C1 88.34(12) . . ?
C3 Mn1 C1 70.59(13) . . ?
C5 Mn1 C1 80.97(12) . . ?
C7 Mn1 P1 94.70(9) . . ?
C6 Mn1 P1 85.82(10) . . ?
C2 Mn1 P1 143.71(10) . . ?
C4 Mn1 P1 88.02(8) . . ?
C3 Mn1 P1 108.33(10) . . ?
C5 Mn1 P1 94.10(8) . . ?
C1 Mn1 P1 175.05(9) . . ?
C8 P1 C9 101.13(11) . . ?
C8 P1 C15 100.80(10) . . ?
C9 P1 C15 101.74(10) . . ?
C8 P1 Mn1 114.02(8) . . ?
C9 P1 Mn1 115.66(7) . . ?
C15 P1 Mn1 120.66(8) . . ?
C2 C1 Mn1 68.43(16) . . ?
C2 C1 H1A 116.8 . . ?
Mn1 C1 H1A 116.8 . . ?
C2 C1 H1B 116.8 . . ?
Mn1 C1 H1B 116.8 . . ?
H1A C1 H1B 113.8 . . ?
C1 C2 C3 126.4(3) . . ?
C1 C2 Mn1 74.32(18) . . ?
C3 C2 Mn1 70.74(17) . . ?
C1 C2 H2 115.7 . . ?
C3 C2 H2 115.7 . . ?
Mn1 C2 H2 115.7 . . ?
C2 C3 C4 122.8(3) . . ?
C2 C3 Mn1 70.25(18) . . ?
C4 C3 Mn1 70.32(18) . . ?
C2 C3 H3 117.2 . . ?
C4 C3 H3 117.2 . . ?
Mn1 C3 H3 117.2 . . ?
C5 C4 C3 125.4(3) . . ?
C5 C4 Mn1 73.63(19) . . ?
C3 C4 Mn1 70.54(18) . . ?
C5 C4 H4 116.2 . . ?
C3 C4 H4 116.2 . . ?
Mn1 C4 H4 116.2 . . ?
C4 C5 Mn1 68.22(17) . . ?
C4 C5 H5A 116.9 . . ?
Mn1 C5 H5A 116.9 . . ?
C4 C5 H5B 116.9 . . ?
Mn1 C5 H5B 116.9 . . ?
H5A C5 H5B 113.9 . . ?
O1 C6 Mn1 176.9(3) . . ?
O2 C7 Mn1 177.0(3) . . ?
C8 C8 P1 174.2(3) 3_766 . ?
C14 C9 C10 119.5(2) . . ?
C14 C9 P1 122.05(18) . . ?
C10 C9 P1 117.98(17) . . ?
C9 C10 C11 119.8(2) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.6(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C14 119.8(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C9 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
C16 C15 C20 118.9(2) . . ?
C16 C15 P1 121.75(18) . . ?
C20 C15 P1 119.29(19) . . ?
C15 C16 C17 120.1(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 120.1(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 120.1(3) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 120.4(3) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C15 120.4(3) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?

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 C1 C2 C3 50.7(3) . . . . ?
C1 C2 C3 C4 -3.2(5) . . . . ?
Mn1 C2 C3 C4 49.0(3) . . . . ?
C1 C2 C3 Mn1 -52.2(3) . . . . ?
C2 C3 C4 C5 3.0(5) . . . . ?
Mn1 C3 C4 C5 51.9(3) . . . . ?
C2 C3 C4 Mn1 -48.9(3) . . . . ?
C3 C4 C5 Mn1 -50.6(3) . . . . ?
C8 P1 C9 C14 -27.4(2) . . . . ?
C15 P1 C9 C14 -131.08(19) . . . . ?
Mn1 P1 C9 C14 96.26(18) . . . . ?
C8 P1 C9 C10 160.23(18) . . . . ?
C15 P1 C9 C10 56.59(19) . . . . ?
Mn1 P1 C9 C10 -76.08(18) . . . . ?
C14 C9 C10 C11 -1.0(3) . . . . ?
P1 C9 C10 C11 171.53(18) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C10 C11 C12 C13 1.6(4) . . . . ?
C11 C12 C13 C14 -1.2(4) . . . . ?
C12 C13 C14 C9 -0.3(4) . . . . ?
C10 C9 C14 C13 1.4(3) . . . . ?
P1 C9 C14 C13 -170.86(19) . . . . ?
C8 P1 C15 C16 140.5(2) . . . . ?
C9 P1 C15 C16 -115.6(2) . . . . ?
Mn1 P1 C15 C16 14.0(2) . . . . ?
C8 P1 C15 C20 -42.0(2) . . . . ?
C9 P1 C15 C20 61.9(2) . . . . ?
Mn1 P1 C15 C20 -168.47(16) . . . . ?
C20 C15 C16 C17 -0.8(4) . . . . ?
P1 C15 C16 C17 176.79(19) . . . . ?
C15 C16 C17 C18 1.0(4) . . . . ?
C16 C17 C18 C19 -0.7(4) . . . . ?
C17 C18 C19 C20 0.3(4) . . . . ?
C18 C19 C20 C15 -0.1(4) . . . . ?
C16 C15 C20 C19 0.4(4) . . . . ?
P1 C15 C20 C19 -177.3(2) . . . . ?

_refine_diff_density_max         0.461
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.077

_shelxl_version_number           2014-1


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
_chemical_properties_physical    
', Air-sensitive,Moisture-sensitive,Oxygen-sensitive'
####################################################################### 
# 
# 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_mo_135zvn14_0m
_database_code_depnum_ccdc_archive 'CCDC 1522569'
_audit_update_record             
;
2016-12-13 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H42 Mn2 O4 P2'
_chemical_formula_sum            'C44 H42 Mn2 O4 P2'
_chemical_formula_weight         806.59

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

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

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

_cell_length_a                   9.5676(4)
_cell_length_b                   10.9197(4)
_cell_length_c                   11.2228(4)
_cell_angle_alpha                105.9466(6)
_cell_angle_beta                 112.2887(6)
_cell_angle_gamma                104.5166(7)
_cell_volume                     956.58(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9980
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      26.39

_exptl_crystal_description       Prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             418
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.368
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.786
_shelx_estimated_absorpt_T_min   0.761
_shelx_estimated_absorpt_T_max   0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6913
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS 2012/1, Sheldrick'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec ImuS'
_diffrn_radiation_monochromator  mirrors
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30153
_diffrn_reflns_av_unetI/netI     0.0071
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.115
_diffrn_reflns_theta_max         25.680
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3641
_reflns_number_gt                3586
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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+0.6505P] 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         3641
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0663
_refine_ls_wR_factor_gt          0.0660
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 0.86352(2) 0.80166(2) 0.61604(2) 0.01397(8) Uani 1 1 d . . . . .
P1 P 0.98540(4) 0.80469(3) 0.82931(3) 0.01073(9) Uani 1 1 d . . . . .
O1 O 1.16310(15) 0.92670(15) 0.59963(13) 0.0387(3) Uani 1 1 d . . . . .
O2 O 0.90371(18) 1.09402(12) 0.72339(13) 0.0358(3) Uani 1 1 d . . . . .
C1 C 1.19998(16) 0.82199(14) 0.91112(15) 0.0137(3) Uani 1 1 d . . . . .
C2 C 1.30401(17) 0.89560(14) 1.05646(15) 0.0166(3) Uani 1 1 d . . . . .
H2 H 1.2642 0.9385 1.1148 0.020 Uiso 1 1 calc R U . . .
C3 C 1.46600(18) 0.90664(15) 1.11664(16) 0.0196(3) Uani 1 1 d . . . . .
H3 H 1.5372 0.9590 1.2154 0.024 Uiso 1 1 calc R U . . .
C4 C 1.52333(18) 0.84129(16) 1.03257(17) 0.0210(3) Uani 1 1 d . . . . .
H4 H 1.6336 0.8483 1.0738 0.025 Uiso 1 1 calc R U . . .
C5 C 1.41982(19) 0.76562(16) 0.88833(17) 0.0218(3) Uani 1 1 d . . . . .
H5 H 1.4586 0.7191 0.8312 0.026 Uiso 1 1 calc R U . . .
C6 C 1.25896(18) 0.75758(15) 0.82692(16) 0.0185(3) Uani 1 1 d . . . . .
H6 H 1.1895 0.7082 0.7276 0.022 Uiso 1 1 calc R U . . .
C7 C 0.88497(16) 0.66201(14) 0.86370(14) 0.0132(3) Uani 1 1 d . . . . .
C8 C 0.78222(18) 0.67277(15) 0.92315(15) 0.0185(3) Uani 1 1 d . . . . .
H8 H 0.7671 0.7568 0.9505 0.022 Uiso 1 1 calc R U . . .
C9 C 0.70167(19) 0.56116(17) 0.94270(17) 0.0241(3) Uani 1 1 d . . . . .
H9 H 0.6306 0.5688 0.9822 0.029 Uiso 1 1 calc R U . . .
C10 C 0.72460(19) 0.43910(16) 0.90485(17) 0.0254(3) Uani 1 1 d . . . . .
H10 H 0.6703 0.3634 0.9194 0.031 Uiso 1 1 calc R U . . .
C11 C 0.82687(19) 0.42724(15) 0.84570(17) 0.0237(3) Uani 1 1 d . . . . .
H11 H 0.8427 0.3434 0.8198 0.028 Uiso 1 1 calc R U . . .
C12 C 0.90629(18) 0.53807(15) 0.82435(15) 0.0180(3) Uani 1 1 d . . . . .
H12 H 0.9753 0.5293 0.7828 0.022 Uiso 1 1 calc R U . . .
C13 C 0.81632(19) 0.58028(15) 0.51802(15) 0.0201(3) Uani 1 1 d . . . . .
H13A H 0.9140 0.5572 0.5356 0.024 Uiso 1 1 calc R U . . .
H13B H 0.7263 0.5126 0.5190 0.024 Uiso 1 1 calc R U . . .
C14 C 0.76969(19) 0.63424(15) 0.41551(15) 0.0205(3) Uani 1 1 d . . . . .
C15 C 0.66374(19) 0.70615(15) 0.40476(15) 0.0216(3) Uani 1 1 d . . . . .
H15 H 0.6660 0.7622 0.3480 0.026 Uiso 1 1 calc R U . . .
C16 C 0.60257(18) 0.74545(16) 0.50047(16) 0.0227(3) Uani 1 1 d . . . . .
C17 C 0.63006(18) 0.70840(17) 0.61501(16) 0.0222(3) Uani 1 1 d . . . . .
H17A H 0.5896 0.6078 0.5925 0.027 Uiso 1 1 calc R U . . .
H17B H 0.6138 0.7638 0.6909 0.027 Uiso 1 1 calc R U . . .
C18 C 0.8482(2) 0.63078(18) 0.32114(17) 0.0294(4) Uani 1 1 d . . . . .
H18A H 0.7811 0.5452 0.2343 0.044 Uiso 1 1 calc R U . . .
H18B H 0.9590 0.6337 0.3706 0.044 Uiso 1 1 calc R U . . .
H18C H 0.8553 0.7112 0.2973 0.044 Uiso 1 1 calc R U . . .
C19 C 0.5222(2) 0.8474(2) 0.48607(19) 0.0365(4) Uani 1 1 d . . . . .
H19A H 0.4027 0.7965 0.4264 0.055 Uiso 1 1 calc R U . . .
H19B H 0.5653 0.9028 0.4427 0.055 Uiso 1 1 calc R U . . .
H19C H 0.5465 0.9091 0.5798 0.055 Uiso 1 1 calc R U . . .
C20 C 1.04682(19) 0.87347(17) 0.60586(15) 0.0233(3) Uani 1 1 d . . . . .
C21 C 0.8854(2) 0.97894(16) 0.68179(16) 0.0230(3) Uani 1 1 d . . . . .
C22 C 0.99884(16) 0.94902(14) 0.96090(14) 0.0130(3) 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 1.7931(16) . ?
Mn1 C21 1.7975(16) . ?
Mn1 C15 2.1372(15) . ?
Mn1 C14 2.1440(14) . ?
Mn1 C16 2.1518(15) . ?
Mn1 C17 2.2046(15) . ?
Mn1 C13 2.2074(14) . ?
Mn1 P1 2.2158(4) . ?
P1 C22 1.7767(14) . ?
P1 C7 1.8332(14) . ?
P1 C1 1.8368(14) . ?
O1 C20 1.157(2) . ?
O2 C21 1.154(2) . ?
C1 C6 1.394(2) . ?
C1 C2 1.394(2) . ?
C2 C3 1.393(2) . ?
C3 C4 1.385(2) . ?
C4 C5 1.387(2) . ?
C5 C6 1.395(2) . ?
C7 C8 1.392(2) . ?
C7 C12 1.3953(19) . ?
C8 C9 1.390(2) . ?
C9 C10 1.383(2) . ?
C10 C11 1.387(2) . ?
C11 C12 1.391(2) . ?
C13 C14 1.409(2) . ?
C14 C15 1.420(2) . ?
C14 C18 1.511(2) . ?
C15 C16 1.425(2) . ?
C16 C17 1.403(2) . ?
C16 C19 1.514(2) . ?
C22 C22 1.203(3) 2_777 ?

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 84.16(7) . . ?
C20 Mn1 C15 106.56(6) . . ?
C21 Mn1 C15 104.94(6) . . ?
C20 Mn1 C14 88.29(6) . . ?
C21 Mn1 C14 137.88(6) . . ?
C15 Mn1 C14 38.75(6) . . ?
C20 Mn1 C16 139.56(6) . . ?
C21 Mn1 C16 87.15(7) . . ?
C15 Mn1 C16 38.80(6) . . ?
C14 Mn1 C16 72.38(6) . . ?
C20 Mn1 C17 176.66(6) . . ?
C21 Mn1 C17 96.82(7) . . ?
C15 Mn1 C17 70.10(6) . . ?
C14 Mn1 C17 88.86(6) . . ?
C16 Mn1 C17 37.54(6) . . ?
C20 Mn1 C13 97.80(7) . . ?
C21 Mn1 C13 174.78(6) . . ?
C15 Mn1 C13 69.88(6) . . ?
C14 Mn1 C13 37.74(6) . . ?
C16 Mn1 C13 88.25(6) . . ?
C17 Mn1 C13 80.95(6) . . ?
C20 Mn1 P1 97.26(5) . . ?
C21 Mn1 P1 94.17(5) . . ?
C15 Mn1 P1 150.63(4) . . ?
C14 Mn1 P1 127.91(4) . . ?
C16 Mn1 P1 122.77(4) . . ?
C17 Mn1 P1 85.86(4) . . ?
C13 Mn1 P1 90.39(4) . . ?
C22 P1 C7 100.52(6) . . ?
C22 P1 C1 100.03(6) . . ?
C7 P1 C1 101.28(6) . . ?
C22 P1 Mn1 111.69(4) . . ?
C7 P1 Mn1 118.49(4) . . ?
C1 P1 Mn1 121.44(5) . . ?
C6 C1 C2 119.31(13) . . ?
C6 C1 P1 119.45(11) . . ?
C2 C1 P1 121.23(10) . . ?
C3 C2 C1 120.36(13) . . ?
C4 C3 C2 120.02(14) . . ?
C3 C4 C5 120.02(13) . . ?
C4 C5 C6 120.18(14) . . ?
C1 C6 C5 120.07(14) . . ?
C8 C7 C12 119.20(13) . . ?
C8 C7 P1 121.25(10) . . ?
C12 C7 P1 119.50(10) . . ?
C9 C8 C7 120.31(14) . . ?
C10 C9 C8 120.23(14) . . ?
C9 C10 C11 119.97(14) . . ?
C10 C11 C12 120.05(14) . . ?
C11 C12 C7 120.23(14) . . ?
C14 C13 Mn1 68.69(8) . . ?
C13 C14 C15 123.22(14) . . ?
C13 C14 C18 119.69(14) . . ?
C15 C14 C18 116.76(14) . . ?
C13 C14 Mn1 73.57(8) . . ?
C15 C14 Mn1 70.36(8) . . ?
C18 C14 Mn1 124.60(11) . . ?
C14 C15 C16 126.15(14) . . ?
C14 C15 Mn1 70.89(8) . . ?
C16 C15 Mn1 71.16(8) . . ?
C17 C16 C15 123.79(14) . . ?
C17 C16 C19 119.08(14) . . ?
C15 C16 C19 116.67(15) . . ?
C17 C16 Mn1 73.27(9) . . ?
C15 C16 Mn1 70.04(8) . . ?
C19 C16 Mn1 124.88(12) . . ?
C16 C17 Mn1 69.19(9) . . ?
O1 C20 Mn1 175.95(15) . . ?
O2 C21 Mn1 177.82(15) . . ?
C22 C22 P1 173.28(17) 2_777 . ?

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 P1 C1 C6 -159.89(11) . . . . ?
C7 P1 C1 C6 97.14(12) . . . . ?
Mn1 P1 C1 C6 -36.66(13) . . . . ?
C22 P1 C1 C2 21.66(12) . . . . ?
C7 P1 C1 C2 -81.31(12) . . . . ?
Mn1 P1 C1 C2 144.90(10) . . . . ?
C6 C1 C2 C3 1.1(2) . . . . ?
P1 C1 C2 C3 179.50(11) . . . . ?
C1 C2 C3 C4 -1.7(2) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C3 C4 C5 C6 1.4(2) . . . . ?
C2 C1 C6 C5 0.8(2) . . . . ?
P1 C1 C6 C5 -177.68(11) . . . . ?
C4 C5 C6 C1 -2.0(2) . . . . ?
C22 P1 C7 C8 27.48(13) . . . . ?
C1 P1 C7 C8 130.05(12) . . . . ?
Mn1 P1 C7 C8 -94.43(11) . . . . ?
C22 P1 C7 C12 -155.18(11) . . . . ?
C1 P1 C7 C12 -52.61(12) . . . . ?
Mn1 P1 C7 C12 82.91(11) . . . . ?
C12 C7 C8 C9 -0.1(2) . . . . ?
P1 C7 C8 C9 177.21(11) . . . . ?
C7 C8 C9 C10 0.8(2) . . . . ?
C8 C9 C10 C11 -0.7(2) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
C10 C11 C12 C7 0.7(2) . . . . ?
C8 C7 C12 C11 -0.6(2) . . . . ?
P1 C7 C12 C11 -178.01(11) . . . . ?
Mn1 C13 C14 C15 -52.27(13) . . . . ?
Mn1 C13 C14 C18 120.88(14) . . . . ?
C13 C14 C15 C16 6.2(2) . . . . ?
C18 C14 C15 C16 -167.12(15) . . . . ?
Mn1 C14 C15 C16 -47.43(15) . . . . ?
C13 C14 C15 Mn1 53.65(13) . . . . ?
C18 C14 C15 Mn1 -119.69(13) . . . . ?
C14 C15 C16 C17 -5.0(3) . . . . ?
Mn1 C15 C16 C17 -52.30(14) . . . . ?
C14 C15 C16 C19 167.22(16) . . . . ?
Mn1 C15 C16 C19 119.89(14) . . . . ?
C14 C15 C16 Mn1 47.33(14) . . . . ?
C15 C16 C17 Mn1 50.95(14) . . . . ?
C19 C16 C17 Mn1 -121.07(15) . . . . ?

_refine_diff_density_max         0.388
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.049

_shelxl_version_number           2013-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: benzene'
_chemical_properties_physical    
', Air-sensitive,Moisture-sensitive,Oxygen-sensitive'
####################################################################### 
# 
# 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_478ZVN15
_database_code_depnum_ccdc_archive 'CCDC 1523217'
_audit_update_record             
;
2016-12-16 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 Mn O3'
_chemical_formula_sum            'C8 H7 Mn O3'
_chemical_formula_weight         206.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   16.3527(4)
_cell_length_b                   6.1392(2)
_cell_length_c                   16.3852(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.7440(10)
_cell_angle_gamma                90
_cell_volume                     1636.69(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      27.48

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.282
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.052
_exptl_absorpt_coefficient_mu    1.571
_shelx_estimated_absorpt_T_min   0.666
_shelx_estimated_absorpt_T_max   0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6659
_exptl_absorpt_correction_T_max  0.9228
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker Smart Apex CCD diffractometer 01-670-01'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            42272
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0935
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.249
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3608
_reflns_number_gt                3285
_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       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0671P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3608
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.1012
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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 0.20154(3) 0.56507(7) 0.55199(3) 0.01528(13) Uani 1 1 d . . . . .
O1 O 0.25568(13) 0.2573(4) 0.42967(13) 0.0297(5) Uani 1 1 d . . . . .
O2 O 0.26311(14) 0.3303(4) 0.70372(13) 0.0280(5) Uani 1 1 d . . . . .
O3 O 0.04588(13) 0.3273(3) 0.56174(14) 0.0280(5) Uani 1 1 d . . . . .
C1 C 0.15464(18) 0.7691(5) 0.44575(18) 0.0253(6) Uani 1 1 d . . . . .
H1A H 0.1959 0.8523 0.4182 0.030 Uiso 1 1 calc R U . . .
H1B H 0.1101 0.7063 0.4075 0.030 Uiso 1 1 calc R U . . .
C2 C 0.13229(19) 0.8537(5) 0.51902(19) 0.0221(6) Uani 1 1 d . . . . .
H2 H 0.0724 0.8481 0.5266 0.027 Uiso 1 1 calc R U . . .
C3 C 0.1866(2) 0.8953(5) 0.5909(2) 0.0231(7) Uani 1 1 d . . . . .
H3 H 0.1606 0.9165 0.6431 0.028 Uiso 1 1 calc R U . . .
C4 C 0.27198(19) 0.8419(5) 0.59872(19) 0.0239(7) Uani 1 1 d . . . . .
H4 H 0.2988 0.8282 0.6561 0.029 Uiso 1 1 calc R U . . .
C5 C 0.31538(17) 0.7540(6) 0.53744(18) 0.0253(7) Uani 1 1 d . . . . .
H5A H 0.3683 0.6821 0.5554 0.030 Uiso 1 1 calc R U . . .
H5B H 0.3162 0.8403 0.4865 0.030 Uiso 1 1 calc R U . . .
C6 C 0.23532(18) 0.3740(5) 0.47876(19) 0.0204(6) Uani 1 1 d . . . . .
C7 C 0.24011(19) 0.4218(5) 0.6449(2) 0.0205(7) Uani 1 1 d . . . . .
C8 C 0.10564(19) 0.4236(4) 0.55837(18) 0.0190(6) Uani 1 1 d . . . . .
Mn2 Mn 0.44951(3) 0.59688(7) 0.30123(3) 0.01533(13) Uani 1 1 d . . . . .
O11 O 0.57340(14) 0.3001(4) 0.24284(14) 0.0313(5) Uani 1 1 d . . . . .
O12 O 0.43774(14) 0.3502(3) 0.45403(13) 0.0261(5) Uani 1 1 d . . . . .
O13 O 0.29809(13) 0.3598(4) 0.24010(14) 0.0273(5) Uani 1 1 d . . . . .
C11 C 0.46410(19) 0.7886(5) 0.18804(18) 0.0272(7) Uani 1 1 d . . . . .
H11A H 0.5149 0.8760 0.1876 0.033 Uiso 1 1 calc R U . . .
H11B H 0.4463 0.7177 0.1350 0.033 Uiso 1 1 calc R U . . .
C12 C 0.4027(2) 0.8732(5) 0.2316(2) 0.0245(7) Uani 1 1 d . . . . .
H12 H 0.3453 0.8584 0.2046 0.029 Uiso 1 1 calc R U . . .
C13 C 0.4097(2) 0.9256(4) 0.3170(2) 0.0239(7) Uani 1 1 d . . . . .
H13 H 0.3572 0.9458 0.3427 0.029 Uiso 1 1 calc R U . . .
C14 C 0.48133(19) 0.8837(4) 0.37092(19) 0.0216(6) Uani 1 1 d . . . . .
H14 H 0.4737 0.8766 0.4306 0.026 Uiso 1 1 calc R U . . .
C15 C 0.55580(18) 0.8013(5) 0.34831(19) 0.0244(7) Uani 1 1 d . . . . .
H15A H 0.5943 0.7384 0.3926 0.029 Uiso 1 1 calc R U . . .
H15B H 0.5831 0.8861 0.3073 0.029 Uiso 1 1 calc R U . . .
C16 C 0.52375(19) 0.4111(5) 0.26538(19) 0.0217(7) Uani 1 1 d . . . . .
C17 C 0.44237(18) 0.4514(4) 0.39571(18) 0.0178(6) Uani 1 1 d . . . . .
C18 C 0.35681(18) 0.4523(5) 0.26211(18) 0.0191(6) 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 C6 1.804(3) . ?
Mn1 C8 1.805(3) . ?
Mn1 C7 1.815(3) . ?
Mn1 C2 2.143(3) . ?
Mn1 C3 2.147(3) . ?
Mn1 C4 2.151(3) . ?
Mn1 C1 2.218(3) . ?
Mn1 C5 2.226(3) . ?
O1 C6 1.151(4) . ?
O2 C7 1.146(4) . ?
O3 C8 1.148(4) . ?
C1 C2 1.390(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.425(5) . ?
C2 H2 1.0000 . ?
C3 C4 1.428(5) . ?
C3 H3 1.0000 . ?
C4 C5 1.395(4) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
Mn2 C17 1.801(3) . ?
Mn2 C16 1.806(3) . ?
Mn2 C18 1.817(3) . ?
Mn2 C14 2.134(3) . ?
Mn2 C12 2.143(3) . ?
Mn2 C13 2.144(3) . ?
Mn2 C15 2.219(3) . ?
Mn2 C11 2.230(3) . ?
O11 C16 1.149(4) . ?
O12 C17 1.149(4) . ?
O13 C18 1.143(4) . ?
C11 C12 1.390(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.430(5) . ?
C12 H12 1.0000 . ?
C13 C14 1.419(4) . ?
C13 H13 1.0000 . ?
C14 C15 1.402(4) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 Mn1 C8 92.94(13) . . ?
C6 Mn1 C7 97.98(13) . . ?
C8 Mn1 C7 87.10(13) . . ?
C6 Mn1 C2 124.01(13) . . ?
C8 Mn1 C2 88.40(12) . . ?
C7 Mn1 C2 137.94(13) . . ?
C6 Mn1 C3 149.71(13) . . ?
C8 Mn1 C3 108.16(12) . . ?
C7 Mn1 C3 104.41(13) . . ?
C2 Mn1 C3 38.82(12) . . ?
C6 Mn1 C4 124.20(12) . . ?
C8 Mn1 C4 142.86(13) . . ?
C7 Mn1 C4 87.45(13) . . ?
C2 Mn1 C4 71.76(12) . . ?
C3 Mn1 C4 38.82(12) . . ?
C6 Mn1 C1 87.14(13) . . ?
C8 Mn1 C1 94.76(12) . . ?
C7 Mn1 C1 174.48(12) . . ?
C2 Mn1 C1 37.13(12) . . ?
C3 Mn1 C1 70.07(12) . . ?
C4 Mn1 C1 87.94(12) . . ?
C6 Mn1 C5 87.28(12) . . ?
C8 Mn1 C5 176.05(12) . . ?
C7 Mn1 C5 96.78(13) . . ?
C2 Mn1 C5 88.21(12) . . ?
C3 Mn1 C5 70.20(12) . . ?
C4 Mn1 C5 37.12(12) . . ?
C1 Mn1 C5 81.31(12) . . ?
C2 C1 Mn1 68.48(17) . . ?
C2 C1 H1A 116.8 . . ?
Mn1 C1 H1A 116.8 . . ?
C2 C1 H1B 116.8 . . ?
Mn1 C1 H1B 116.8 . . ?
H1A C1 H1B 113.8 . . ?
C1 C2 C3 125.8(3) . . ?
C1 C2 Mn1 74.39(18) . . ?
C3 C2 Mn1 70.75(17) . . ?
C1 C2 H2 116.1 . . ?
C3 C2 H2 116.1 . . ?
Mn1 C2 H2 116.1 . . ?
C2 C3 C4 123.7(3) . . ?
C2 C3 Mn1 70.43(17) . . ?
C4 C3 Mn1 70.74(17) . . ?
C2 C3 H3 116.6 . . ?
C4 C3 H3 116.6 . . ?
Mn1 C3 H3 116.6 . . ?
C5 C4 C3 126.0(3) . . ?
C5 C4 Mn1 74.39(17) . . ?
C3 C4 Mn1 70.44(17) . . ?
C5 C4 H4 115.9 . . ?
C3 C4 H4 115.9 . . ?
Mn1 C4 H4 115.9 . . ?
C4 C5 Mn1 68.49(16) . . ?
C4 C5 H5A 116.8 . . ?
Mn1 C5 H5A 116.8 . . ?
C4 C5 H5B 116.8 . . ?
Mn1 C5 H5B 116.8 . . ?
H5A C5 H5B 113.8 . . ?
O1 C6 Mn1 177.4(3) . . ?
O2 C7 Mn1 178.8(3) . . ?
O3 C8 Mn1 177.7(3) . . ?
C17 Mn2 C16 94.01(13) . . ?
C17 Mn2 C18 86.42(13) . . ?
C16 Mn2 C18 98.10(13) . . ?
C17 Mn2 C14 88.99(12) . . ?
C16 Mn2 C14 123.99(13) . . ?
C18 Mn2 C14 137.88(13) . . ?
C17 Mn2 C12 143.11(13) . . ?
C16 Mn2 C12 122.87(13) . . ?
C18 Mn2 C12 87.58(13) . . ?
C14 Mn2 C12 71.75(13) . . ?
C17 Mn2 C13 108.43(13) . . ?
C16 Mn2 C13 148.86(13) . . ?
C18 Mn2 C13 104.44(13) . . ?
C14 Mn2 C13 38.72(12) . . ?
C12 Mn2 C13 38.97(13) . . ?
C17 Mn2 C15 95.60(12) . . ?
C16 Mn2 C15 86.66(12) . . ?
C18 Mn2 C15 174.70(12) . . ?
C14 Mn2 C15 37.52(11) . . ?
C12 Mn2 C15 87.88(12) . . ?
C13 Mn2 C15 70.28(12) . . ?
C17 Mn2 C11 176.68(13) . . ?
C16 Mn2 C11 86.08(12) . . ?
C18 Mn2 C11 96.86(13) . . ?
C14 Mn2 C11 88.21(12) . . ?
C12 Mn2 C11 36.99(12) . . ?
C13 Mn2 C11 70.28(13) . . ?
C15 Mn2 C11 81.09(12) . . ?
C12 C11 Mn2 68.12(17) . . ?
C12 C11 H11A 116.9 . . ?
Mn2 C11 H11A 116.9 . . ?
C12 C11 H11B 116.9 . . ?
Mn2 C11 H11B 116.9 . . ?
H11A C11 H11B 113.9 . . ?
C11 C12 C13 126.6(3) . . ?
C11 C12 Mn2 74.89(18) . . ?
C13 C12 Mn2 70.57(17) . . ?
C11 C12 H12 115.7 . . ?
C13 C12 H12 115.7 . . ?
Mn2 C12 H12 115.7 . . ?
C14 C13 C12 123.3(3) . . ?
C14 C13 Mn2 70.25(17) . . ?
C12 C13 Mn2 70.46(18) . . ?
C14 C13 H13 116.8 . . ?
C12 C13 H13 116.8 . . ?
Mn2 C13 H13 116.8 . . ?
C15 C14 C13 125.9(3) . . ?
C15 C14 Mn2 74.52(17) . . ?
C13 C14 Mn2 71.02(17) . . ?
C15 C14 H14 116.1 . . ?
C13 C14 H14 116.1 . . ?
Mn2 C14 H14 116.1 . . ?
C14 C15 Mn2 67.97(16) . . ?
C14 C15 H15A 116.9 . . ?
Mn2 C15 H15A 116.9 . . ?
C14 C15 H15B 116.9 . . ?
Mn2 C15 H15B 116.9 . . ?
H15A C15 H15B 113.9 . . ?
O11 C16 Mn2 177.0(3) . . ?
O12 C17 Mn2 177.0(3) . . ?
O13 C18 Mn2 177.8(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
Mn1 C1 C2 C3 51.4(3) . . . . ?
C1 C2 C3 C4 -4.1(5) . . . . ?
Mn1 C2 C3 C4 48.8(3) . . . . ?
C1 C2 C3 Mn1 -52.9(3) . . . . ?
C2 C3 C4 C5 3.6(5) . . . . ?
Mn1 C3 C4 C5 52.3(3) . . . . ?
C2 C3 C4 Mn1 -48.7(3) . . . . ?
C3 C4 C5 Mn1 -50.8(3) . . . . ?
Mn2 C11 C12 C13 51.0(3) . . . . ?
C11 C12 C13 C14 -4.1(5) . . . . ?
Mn2 C12 C13 C14 48.6(3) . . . . ?
C11 C12 C13 Mn2 -52.7(3) . . . . ?
C12 C13 C14 C15 4.7(5) . . . . ?
Mn2 C13 C14 C15 53.3(3) . . . . ?
C12 C13 C14 Mn2 -48.7(3) . . . . ?
C13 C14 C15 Mn2 -51.9(3) . . . . ?

_refine_diff_density_max         0.443
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.108


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: pentane'
_chemical_properties_physical    ', Air-sensitive,Oxygen-sensitive'
