# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_dr155
_database_code_depnum_ccdc_archive 'CCDC 1478568'
_audit_update_record             
;
2016-05-06 deposited with the CCDC.
2016-05-31 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         ?
_chemical_formula_sum            'C37.50 H32.50 Br Cl10.50 Mn N3 O3 P2'
_chemical_formula_weight         1142.18

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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                   12.8806(3)
_cell_length_b                   15.3050(3)
_cell_length_c                   15.3667(3)
_cell_angle_alpha                113.7345(11)
_cell_angle_beta                 98.8175(12)
_cell_angle_gamma                110.0101(11)
_cell_volume                     2452.06(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9897
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      28.30

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_F_000             1142
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.759
_shelx_estimated_absorpt_T_min   0.473
_shelx_estimated_absorpt_T_max   0.844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4631
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20923
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.801
_diffrn_reflns_theta_max         28.312
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             11858
_reflns_number_gt                9706
_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       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'
_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)+(0.0576P)²+1.8550P] 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         11858
_refine_ls_number_parameters     541
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1275
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.074
_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 0.35458(3) 0.06762(3) 0.37268(2) 0.02279(9) Uani 1 1 d . . . . .
Br1 Br 0.13257(3) 0.33729(2) 0.15187(2) 0.03750(8) Uani 1 1 d . . . . .
P1 P 0.43199(5) 0.24090(5) 0.41983(5) 0.02545(13) Uani 1 1 d . . . . .
P2 P 0.24303(6) -0.10960(5) 0.28818(4) 0.02532(13) Uani 1 1 d . . . . .
O1 O 0.5660(2) 0.05477(19) 0.3242(2) 0.0539(6) Uani 1 1 d . . . . .
O2 O 0.4686(2) 0.08827(19) 0.56555(16) 0.0540(6) Uani 1 1 d . . . . .
O3 O 0.1674(2) 0.09078(18) 0.45935(18) 0.0512(5) Uani 1 1 d . . . . .
N1 N 0.26884(17) 0.05561(16) 0.24116(15) 0.0251(4) Uani 1 1 d . . . . .
N2 N 0.37297(19) 0.24056(16) 0.31350(16) 0.0302(4) Uani 1 1 d . . . . .
N3 N 0.15917(19) -0.12609(16) 0.18118(15) 0.0298(4) Uani 1 1 d . . . . .
C1 C 0.2927(2) 0.14342(19) 0.23004(18) 0.0285(5) Uani 1 1 d . . . . .
C2 C 0.2391(3) 0.1366(2) 0.1404(2) 0.0387(6) Uani 1 1 d . . . . .
H2A H 0.2582 0.1984 0.1330 0.046 Uiso 1 1 calc R U . . .
C3 C 0.1574(3) 0.0378(2) 0.0624(2) 0.0423(7) Uani 1 1 d . . . . .
H3A H 0.1202 0.0316 0.0004 0.051 Uiso 1 1 calc R U . . .
C4 C 0.1284(3) -0.0522(2) 0.07237(19) 0.0371(6) Uani 1 1 d . . . . .
H4A H 0.0716 -0.1201 0.0186 0.045 Uiso 1 1 calc R U . . .
C5 C 0.1853(2) -0.04016(19) 0.16393(18) 0.0271(5) Uani 1 1 d . . . . .
C6 C 0.4102(3) 0.3368(2) 0.3033(2) 0.0409(6) Uani 1 1 d . . . . .
H6A H 0.4666 0.3986 0.3680 0.061 Uiso 1 1 calc R U . . .
H6B H 0.4474 0.3283 0.2513 0.061 Uiso 1 1 calc R U . . .
H6C H 0.3417 0.3479 0.2839 0.061 Uiso 1 1 calc R U . . .
C7 C 0.0755(3) -0.2330(2) 0.0984(2) 0.0399(6) Uani 1 1 d . . . . .
H7A H 0.0661 -0.2851 0.1220 0.060 Uiso 1 1 calc R U . . .
H7B H -0.0005 -0.2339 0.0763 0.060 Uiso 1 1 calc R U . . .
H7C H 0.1051 -0.2514 0.0418 0.060 Uiso 1 1 calc R U . . .
C8 C 0.3928(2) 0.32281(19) 0.5196(2) 0.0308(5) Uani 1 1 d . . . . .
C9 C 0.3225(2) 0.3702(2) 0.5028(2) 0.0376(6) Uani 1 1 d . . . . .
H9A H 0.2975 0.3649 0.4387 0.045 Uiso 1 1 calc R U . . .
C10 C 0.2894(3) 0.4256(2) 0.5813(3) 0.0487(7) Uani 1 1 d . . . . .
H10A H 0.2411 0.4577 0.5701 0.058 Uiso 1 1 calc R U . . .
C11 C 0.3250(3) 0.4346(3) 0.6740(3) 0.0512(8) Uani 1 1 d . . . . .
H11A H 0.3028 0.4740 0.7270 0.061 Uiso 1 1 calc R U . . .
C12 C 0.3933(3) 0.3867(3) 0.6911(2) 0.0470(7) Uani 1 1 d . . . . .
H12A H 0.4173 0.3922 0.7555 0.056 Uiso 1 1 calc R U . . .
C13 C 0.4268(3) 0.3306(2) 0.6137(2) 0.0376(6) Uani 1 1 d . . . . .
H13A H 0.4734 0.2971 0.6252 0.045 Uiso 1 1 calc R U . . .
C14 C 0.5886(2) 0.31693(19) 0.45186(19) 0.0280(5) Uani 1 1 d . . . . .
C15 C 0.6632(2) 0.3934(2) 0.5500(2) 0.0337(5) Uani 1 1 d . . . . .
H15A H 0.6314 0.4136 0.6026 0.040 Uiso 1 1 calc R U . . .
C16 C 0.7833(3) 0.4401(2) 0.5716(2) 0.0415(6) Uani 1 1 d . . . . .
H16A H 0.8339 0.4917 0.6390 0.050 Uiso 1 1 calc R U . . .
C17 C 0.8301(3) 0.4118(2) 0.4952(2) 0.0426(6) Uani 1 1 d . . . . .
H17A H 0.9128 0.4423 0.5104 0.051 Uiso 1 1 calc R U . . .
C18 C 0.7567(3) 0.3393(2) 0.3969(2) 0.0413(6) Uani 1 1 d . . . . .
H18A H 0.7887 0.3222 0.3441 0.050 Uiso 1 1 calc R U . . .
C19 C 0.6368(2) 0.2916(2) 0.3752(2) 0.0346(5) Uani 1 1 d . . . . .
H19A H 0.5867 0.2411 0.3074 0.041 Uiso 1 1 calc R U . . .
C20 C 0.1425(2) -0.1569(2) 0.34708(19) 0.0313(5) Uani 1 1 d . . . . .
C21 C 0.0257(3) -0.1759(2) 0.3170(2) 0.0389(6) Uani 1 1 d . . . . .
H21A H -0.0057 -0.1734 0.2584 0.047 Uiso 1 1 calc R U . . .
C22 C -0.0448(3) -0.1984(3) 0.3721(3) 0.0496(7) Uani 1 1 d . . . . .
H22A H -0.1243 -0.2109 0.3516 0.060 Uiso 1 1 calc R U . . .
C23 C 0.0008(3) -0.2024(3) 0.4570(3) 0.0518(8) Uani 1 1 d . . . . .
H23A H -0.0479 -0.2184 0.4944 0.062 Uiso 1 1 calc R U . . .
C24 C 0.1156(3) -0.1837(3) 0.4880(2) 0.0491(7) Uani 1 1 d . . . . .
H24A H 0.1460 -0.1867 0.5465 0.059 Uiso 1 1 calc R U . . .
C25 C 0.1878(3) -0.1602(2) 0.4336(2) 0.0387(6) Uani 1 1 d . . . . .
H25A H 0.2676 -0.1464 0.4554 0.046 Uiso 1 1 calc R U . . .
C26 C 0.2958(2) -0.20908(19) 0.23878(19) 0.0309(5) Uani 1 1 d . . . . .
C27 C 0.2608(3) -0.3004(2) 0.2482(2) 0.0410(6) Uani 1 1 d . . . . .
H27A H 0.2101 -0.3115 0.2855 0.049 Uiso 1 1 calc R U . . .
C28 C 0.3005(3) -0.3758(2) 0.2025(3) 0.0511(8) Uani 1 1 d . . . . .
H28A H 0.2754 -0.4388 0.2081 0.061 Uiso 1 1 calc R U . . .
C29 C 0.3745(3) -0.3603(3) 0.1502(3) 0.0549(9) Uani 1 1 d . . . . .
H29A H 0.4018 -0.4118 0.1204 0.066 Uiso 1 1 calc R U . . .
C30 C 0.4101(3) -0.2697(3) 0.1403(3) 0.0546(8) Uani 1 1 d . . . . .
H30A H 0.4621 -0.2585 0.1040 0.065 Uiso 1 1 calc R U . . .
C31 C 0.3694(3) -0.1954(2) 0.1838(2) 0.0437(7) Uani 1 1 d . . . . .
H31A H 0.3925 -0.1340 0.1756 0.052 Uiso 1 1 calc R U . . .
C32 C 0.4824(2) 0.0579(2) 0.3372(2) 0.0337(5) Uani 1 1 d . . . . .
C33 C 0.4254(2) 0.0800(2) 0.48994(19) 0.0329(5) Uani 1 1 d . . . . .
C34 C 0.2360(2) 0.0813(2) 0.42318(19) 0.0324(5) Uani 1 1 d . . . . .
C35 C 0.2883(3) 0.3122(3) -0.0217(3) 0.0559(8) Uani 1 1 d . . . . .
H35A H 0.2424 0.3253 0.0251 0.067 Uiso 1 1 calc R U . . .
Cl1 Cl 0.23102(15) 0.17547(9) -0.09941(10) 0.0981(4) Uani 1 1 d . . . . .
Cl2 Cl 0.27198(15) 0.37286(11) -0.09358(10) 0.0968(4) Uani 1 1 d . . . . .
Cl3 Cl 0.43521(11) 0.36749(12) 0.05134(10) 0.0945(4) Uani 1 1 d . . . . .
C36 C -0.0332(3) 0.1818(3) 0.2448(2) 0.0461(7) Uani 1 1 d . . . . .
H36A H -0.0029 0.1995 0.1949 0.055 Uiso 1 1 calc R U . . .
Cl4 Cl 0.01489(8) 0.29967(7) 0.35867(6) 0.0550(2) Uani 1 1 d . . . . .
Cl5 Cl 0.01799(12) 0.09669(10) 0.26337(11) 0.0828(3) Uani 1 1 d . . . . .
Cl6 Cl -0.18646(11) 0.11594(10) 0.19647(11) 0.0983(4) Uani 1 1 d . . . . .
C37 C -0.0879(3) 0.4335(3) 0.1621(3) 0.0548(8) Uani 1 1 d D . . . .
H37A H -0.0264 0.4074 0.1624 0.066 Uiso 1 1 calc R U . . .
Cl7 Cl -0.22148(16) 0.32868(12) 0.12868(12) 0.1172(6) Uani 1 1 d D . . . .
Cl8 Cl -0.09022(15) 0.47823(10) 0.07492(10) 0.0934(4) Uani 1 1 d D . . . .
Cl9 Cl -0.05102(10) 0.53771(10) 0.28343(8) 0.0851(4) Uani 1 1 d D . . . .
C38 C 0.4573(14) -0.0108(14) -0.0154(11) 0.147(5) Uani 0.5 1 d D U P A -1
H38A H 0.3738 -0.0661 -0.0532 0.176 Uiso 0.5 1 calc R U P A -1
Cl10 Cl 0.4930(6) 0.0167(5) 0.1038(4) 0.172(2) Uani 0.5 1 d D U P A -1
Cl11 Cl 0.5466(9) -0.0548(11) -0.0690(5) 0.319(6) Uani 0.5 1 d D U P A -1
Cl12 Cl 0.4742(5) 0.1069(5) -0.0146(6) 0.205(3) Uani 0.5 1 d D 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 C33 1.794(3) . ?
Mn1 C32 1.846(3) . ?
Mn1 C34 1.852(3) . ?
Mn1 N1 2.0532(19) . ?
Mn1 P1 2.2305(7) . ?
Mn1 P2 2.2435(7) . ?
P1 N2 1.690(2) . ?
P1 C14 1.815(3) . ?
P1 C8 1.817(3) . ?
P2 N3 1.694(2) . ?
P2 C20 1.807(3) . ?
P2 C26 1.815(3) . ?
O1 C32 1.137(3) . ?
O2 C33 1.145(3) . ?
O3 C34 1.133(3) . ?
N1 C5 1.358(3) . ?
N1 C1 1.360(3) . ?
N2 C1 1.390(3) . ?
N2 C6 1.467(3) . ?
N3 C5 1.385(3) . ?
N3 C7 1.468(3) . ?
C1 C2 1.389(3) . ?
C2 C3 1.377(4) . ?
C3 C4 1.376(4) . ?
C4 C5 1.390(3) . ?
C8 C13 1.389(4) . ?
C8 C9 1.394(4) . ?
C9 C10 1.391(4) . ?
C10 C11 1.362(5) . ?
C11 C12 1.381(5) . ?
C12 C13 1.389(4) . ?
C14 C15 1.391(4) . ?
C14 C19 1.395(4) . ?
C15 C16 1.382(4) . ?
C16 C17 1.385(4) . ?
C17 C18 1.378(4) . ?
C18 C19 1.379(4) . ?
C20 C21 1.392(4) . ?
C20 C25 1.396(4) . ?
C21 C22 1.385(4) . ?
C22 C23 1.381(5) . ?
C23 C24 1.371(5) . ?
C24 C25 1.394(4) . ?
C26 C31 1.382(4) . ?
C26 C27 1.389(3) . ?
C27 C28 1.395(4) . ?
C28 C29 1.359(5) . ?
C29 C30 1.383(5) . ?
C30 C31 1.385(4) . ?
C35 Cl1 1.735(4) . ?
C35 Cl2 1.736(4) . ?
C35 Cl3 1.745(4) . ?
C36 Cl5 1.744(3) . ?
C36 Cl6 1.746(4) . ?
C36 Cl4 1.750(3) . ?
C37 Cl7 1.725(4) . ?
C37 Cl8 1.734(4) . ?
C37 Cl9 1.750(4) . ?
C38 Cl10 1.653(13) . ?
C38 Cl11 1.682(13) . ?
C38 Cl12 1.734(15) . ?

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
C33 Mn1 C32 86.52(12) . . ?
C33 Mn1 C34 86.89(12) . . ?
C32 Mn1 C34 173.34(12) . . ?
C33 Mn1 N1 177.59(10) . . ?
C32 Mn1 N1 95.82(10) . . ?
C34 Mn1 N1 90.76(10) . . ?
C33 Mn1 P1 97.62(8) . . ?
C32 Mn1 P1 90.90(8) . . ?
C34 Mn1 P1 89.00(8) . . ?
N1 Mn1 P1 81.78(6) . . ?
C33 Mn1 P2 98.28(8) . . ?
C32 Mn1 P2 93.67(8) . . ?
C34 Mn1 P2 88.26(8) . . ?
N1 Mn1 P2 82.18(6) . . ?
P1 Mn1 P2 163.69(3) . . ?
N2 P1 C14 103.36(11) . . ?
N2 P1 C8 107.51(11) . . ?
C14 P1 C8 105.33(11) . . ?
N2 P1 Mn1 102.50(7) . . ?
C14 P1 Mn1 120.62(8) . . ?
C8 P1 Mn1 116.09(8) . . ?
N3 P2 C20 106.12(12) . . ?
N3 P2 C26 102.12(11) . . ?
C20 P2 C26 105.62(12) . . ?
N3 P2 Mn1 101.24(7) . . ?
C20 P2 Mn1 113.90(8) . . ?
C26 P2 Mn1 125.51(9) . . ?
C5 N1 C1 118.46(19) . . ?
C5 N1 Mn1 120.63(15) . . ?
C1 N1 Mn1 120.90(16) . . ?
C1 N2 C6 118.9(2) . . ?
C1 N2 P1 118.26(16) . . ?
C6 N2 P1 122.67(18) . . ?
C5 N3 C7 118.9(2) . . ?
C5 N3 P2 119.08(17) . . ?
C7 N3 P2 120.87(17) . . ?
N1 C1 C2 121.8(2) . . ?
N1 C1 N2 116.4(2) . . ?
C2 C1 N2 121.8(2) . . ?
C3 C2 C1 118.2(2) . . ?
C4 C3 C2 121.4(2) . . ?
C3 C4 C5 117.7(2) . . ?
N1 C5 N3 116.3(2) . . ?
N1 C5 C4 122.3(2) . . ?
N3 C5 C4 121.4(2) . . ?
C13 C8 C9 119.3(2) . . ?
C13 C8 P1 117.98(19) . . ?
C9 C8 P1 122.5(2) . . ?
C10 C9 C8 119.1(3) . . ?
C11 C10 C9 121.2(3) . . ?
C10 C11 C12 120.2(3) . . ?
C11 C12 C13 119.6(3) . . ?
C12 C13 C8 120.5(3) . . ?
C15 C14 C19 118.8(2) . . ?
C15 C14 P1 123.00(19) . . ?
C19 C14 P1 117.98(19) . . ?
C16 C15 C14 120.4(2) . . ?
C15 C16 C17 120.0(3) . . ?
C18 C17 C16 120.0(3) . . ?
C17 C18 C19 120.1(3) . . ?
C18 C19 C14 120.5(3) . . ?
C21 C20 C25 119.3(2) . . ?
C21 C20 P2 121.8(2) . . ?
C25 C20 P2 118.3(2) . . ?
C22 C21 C20 120.3(3) . . ?
C23 C22 C21 119.7(3) . . ?
C24 C23 C22 120.8(3) . . ?
C23 C24 C25 120.1(3) . . ?
C24 C25 C20 119.8(3) . . ?
C31 C26 C27 118.8(3) . . ?
C31 C26 P2 117.48(19) . . ?
C27 C26 P2 123.6(2) . . ?
C26 C27 C28 119.7(3) . . ?
C29 C28 C27 120.9(3) . . ?
C28 C29 C30 120.0(3) . . ?
C29 C30 C31 119.5(3) . . ?
C26 C31 C30 121.1(3) . . ?
O1 C32 Mn1 173.8(3) . . ?
O2 C33 Mn1 178.4(3) . . ?
O3 C34 Mn1 175.9(2) . . ?
Cl1 C35 Cl2 110.0(2) . . ?
Cl1 C35 Cl3 111.5(2) . . ?
Cl2 C35 Cl3 110.8(2) . . ?
Cl5 C36 Cl6 108.49(18) . . ?
Cl5 C36 Cl4 110.47(19) . . ?
Cl6 C36 Cl4 110.30(18) . . ?
Cl7 C37 Cl8 110.6(2) . . ?
Cl7 C37 Cl9 110.8(2) . . ?
Cl8 C37 Cl9 110.5(2) . . ?
Cl10 C38 Cl11 110.0(7) . . ?
Cl10 C38 Cl12 106.8(9) . . ?
Cl11 C38 Cl12 110.2(10) . . ?

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
C14 P1 N2 C1 129.1(2) . . . . ?
C8 P1 N2 C1 -119.8(2) . . . . ?
Mn1 P1 N2 C1 3.0(2) . . . . ?
C14 P1 N2 C6 -45.7(2) . . . . ?
C8 P1 N2 C6 65.4(2) . . . . ?
Mn1 P1 N2 C6 -171.8(2) . . . . ?
C20 P2 N3 C5 127.50(19) . . . . ?
C26 P2 N3 C5 -122.1(2) . . . . ?
Mn1 P2 N3 C5 8.3(2) . . . . ?
C20 P2 N3 C7 -64.6(2) . . . . ?
C26 P2 N3 C7 45.8(2) . . . . ?
Mn1 P2 N3 C7 176.2(2) . . . . ?
C5 N1 C1 C2 -3.8(4) . . . . ?
Mn1 N1 C1 C2 177.5(2) . . . . ?
C5 N1 C1 N2 175.8(2) . . . . ?
Mn1 N1 C1 N2 -3.0(3) . . . . ?
C6 N2 C1 N1 174.6(2) . . . . ?
P1 N2 C1 N1 -0.5(3) . . . . ?
C6 N2 C1 C2 -5.9(4) . . . . ?
P1 N2 C1 C2 179.1(2) . . . . ?
N1 C1 C2 C3 1.8(4) . . . . ?
N2 C1 C2 C3 -177.7(3) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C1 N1 C5 N3 -176.2(2) . . . . ?
Mn1 N1 C5 N3 2.5(3) . . . . ?
C1 N1 C5 C4 3.7(4) . . . . ?
Mn1 N1 C5 C4 -177.5(2) . . . . ?
C7 N3 C5 N1 -175.9(2) . . . . ?
P2 N3 C5 N1 -7.7(3) . . . . ?
C7 N3 C5 C4 4.2(4) . . . . ?
P2 N3 C5 C4 172.3(2) . . . . ?
C3 C4 C5 N1 -1.6(4) . . . . ?
C3 C4 C5 N3 178.3(3) . . . . ?
N2 P1 C8 C13 176.7(2) . . . . ?
C14 P1 C8 C13 -73.5(2) . . . . ?
Mn1 P1 C8 C13 62.7(2) . . . . ?
N2 P1 C8 C9 2.1(3) . . . . ?
C14 P1 C8 C9 111.8(2) . . . . ?
Mn1 P1 C8 C9 -111.9(2) . . . . ?
C13 C8 C9 C10 0.9(4) . . . . ?
P1 C8 C9 C10 175.5(2) . . . . ?
C8 C9 C10 C11 0.4(5) . . . . ?
C9 C10 C11 C12 -1.3(5) . . . . ?
C10 C11 C12 C13 0.9(5) . . . . ?
C11 C12 C13 C8 0.4(5) . . . . ?
C9 C8 C13 C12 -1.3(4) . . . . ?
P1 C8 C13 C12 -176.1(2) . . . . ?
N2 P1 C14 C15 137.3(2) . . . . ?
C8 P1 C14 C15 24.6(2) . . . . ?
Mn1 P1 C14 C15 -109.1(2) . . . . ?
N2 P1 C14 C19 -47.4(2) . . . . ?
C8 P1 C14 C19 -160.0(2) . . . . ?
Mn1 P1 C14 C19 66.2(2) . . . . ?
C19 C14 C15 C16 -2.6(4) . . . . ?
P1 C14 C15 C16 172.7(2) . . . . ?
C14 C15 C16 C17 0.7(4) . . . . ?
C15 C16 C17 C18 2.0(4) . . . . ?
C16 C17 C18 C19 -2.7(4) . . . . ?
C17 C18 C19 C14 0.8(4) . . . . ?
C15 C14 C19 C18 1.9(4) . . . . ?
P1 C14 C19 C18 -173.6(2) . . . . ?
N3 P2 C20 C21 -13.7(3) . . . . ?
C26 P2 C20 C21 -121.6(2) . . . . ?
Mn1 P2 C20 C21 96.8(2) . . . . ?
N3 P2 C20 C25 175.1(2) . . . . ?
C26 P2 C20 C25 67.2(2) . . . . ?
Mn1 P2 C20 C25 -74.4(2) . . . . ?
C25 C20 C21 C22 -0.4(4) . . . . ?
P2 C20 C21 C22 -171.4(2) . . . . ?
C20 C21 C22 C23 -0.3(5) . . . . ?
C21 C22 C23 C24 0.5(5) . . . . ?
C22 C23 C24 C25 0.0(5) . . . . ?
C23 C24 C25 C20 -0.7(5) . . . . ?
C21 C20 C25 C24 0.8(4) . . . . ?
P2 C20 C25 C24 172.2(2) . . . . ?
N3 P2 C26 C31 65.2(2) . . . . ?
C20 P2 C26 C31 176.0(2) . . . . ?
Mn1 P2 C26 C31 -48.2(3) . . . . ?
N3 P2 C26 C27 -110.8(2) . . . . ?
C20 P2 C26 C27 0.0(3) . . . . ?
Mn1 P2 C26 C27 135.8(2) . . . . ?
C31 C26 C27 C28 0.2(4) . . . . ?
P2 C26 C27 C28 176.1(2) . . . . ?
C26 C27 C28 C29 1.0(5) . . . . ?
C27 C28 C29 C30 -1.0(5) . . . . ?
C28 C29 C30 C31 -0.2(5) . . . . ?
C27 C26 C31 C30 -1.4(5) . . . . ?
P2 C26 C31 C30 -177.6(3) . . . . ?
C29 C30 C31 C26 1.4(5) . . . . ?

_refine_diff_density_max         1.212
_refine_diff_density_min         -0.736
_refine_diff_density_rms         0.083

####################################################################### 
# 
# 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_dr171
_database_code_depnum_ccdc_archive 'CCDC 1478569'
_audit_update_record             
;
2016-05-06 deposited with the CCDC.
2016-05-31 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         ?
_chemical_formula_sum            'C21 H17 Br Mn N2 O3 P'
_chemical_formula_weight         511.18

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   8.3120(2)
_cell_length_b                   11.1704(3)
_cell_length_c                   11.8045(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.6715(16)
_cell_angle_gamma                90
_cell_volume                     1038.34(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    7022
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      28.35

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.662
_shelx_estimated_absorpt_T_min   0.523
_shelx_estimated_absorpt_T_max   0.618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5953
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8709
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.821
_diffrn_reflns_theta_max         28.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4779
_reflns_number_gt                4564
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.907
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.998

_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       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'
_refine_special_details          
; 
 Refined as a 2-component inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0088P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.056(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4779
_refine_ls_number_parameters     272
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0240
_refine_ls_wR_factor_ref         0.0582
_refine_ls_wR_factor_gt          0.0577
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_restrained_S_all      0.937
_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 0.54455(6) 0.20736(4) 0.73776(4) 0.02147(11) Uani 1 1 d D . . . .
Br1 Br 0.37697(4) 0.08470(3) 0.56183(3) 0.02580(9) Uani 0.93 1 d . . P A 1
C19 C 0.6611(10) 0.3020(5) 0.8539(6) 0.0410(8) Uani 0.93 1 d D . P A 1
O1 O 0.7363(5) 0.3679(3) 0.9324(3) 0.0410(8) Uani 0.93 1 d D . P A 1
Br1' Br 0.6823(9) 0.3466(9) 0.8774(7) 0.046(2) Uani 0.07 1 d . . P A 2
O1' O 0.326(6) 0.054(4) 0.528(3) 0.0410(8) Uani 0.07 1 d D . P A 2
C19' C 0.428(7) 0.113(5) 0.613(4) 0.0410(8) Uani 0.07 1 d D . P A 2
P1 P 0.68845(10) 0.03745(7) 0.81586(7) 0.02161(16) Uani 1 1 d . . . . .
O2 O 0.2943(4) 0.1708(3) 0.8632(2) 0.0463(7) Uani 1 1 d . . . . .
O3 O 0.3368(4) 0.4105(3) 0.6065(3) 0.0491(7) Uani 1 1 d . . . . .
N1 N 0.8289(4) 0.0260(3) 0.7391(2) 0.0259(6) Uani 1 1 d . . . . .
N2 N 0.7296(3) 0.2119(3) 0.6545(2) 0.0220(5) Uani 1 1 d . . . . .
C1 C 0.8382(4) 0.1195(3) 0.6650(3) 0.0229(6) Uani 1 1 d . . . . .
C2 C 0.9598(5) 0.1206(3) 0.6055(3) 0.0314(8) Uani 1 1 d . . . . .
H2A H 1.0359 0.0552 0.6141 0.038 Uiso 1 1 calc R U . . .
C3 C 0.9682(5) 0.2163(4) 0.5348(3) 0.0351(8) Uani 1 1 d . . . . .
H3A H 1.0493 0.2173 0.4935 0.042 Uiso 1 1 calc R U . . .
C4 C 0.8574(5) 0.3114(4) 0.5242(3) 0.0338(8) Uani 1 1 d . . . . .
H4A H 0.8622 0.3792 0.4769 0.041 Uiso 1 1 calc R U . . .
C5 C 0.7404(4) 0.3050(3) 0.5842(3) 0.0266(7) Uani 1 1 d . . . . .
H5A H 0.6630 0.3696 0.5757 0.032 Uiso 1 1 calc R U . . .
C6 C 0.9639(5) -0.0642(3) 0.7698(3) 0.0367(8) Uani 1 1 d . . . . .
H6A H 0.9400 -0.1244 0.8226 0.055 Uiso 1 1 calc R U . . .
H6B H 0.9692 -0.1030 0.6965 0.055 Uiso 1 1 calc R U . . .
H6C H 1.0730 -0.0256 0.8106 0.055 Uiso 1 1 calc R U . . .
C7 C 0.5730(4) -0.1035(3) 0.7933(3) 0.0232(6) Uani 1 1 d . . . . .
C8 C 0.5867(4) -0.1874(3) 0.7094(3) 0.0259(6) Uani 1 1 d . . . . .
H8A H 0.6600 -0.1723 0.6636 0.031 Uiso 1 1 calc R U . . .
C9 C 0.4941(5) -0.2927(3) 0.6925(3) 0.0322(7) Uani 1 1 d . . . . .
H9A H 0.5051 -0.3500 0.6360 0.039 Uiso 1 1 calc R U . . .
C10 C 0.3855(5) -0.3146(3) 0.7578(3) 0.0376(8) Uani 1 1 d . . . . .
H10A H 0.3236 -0.3875 0.7473 0.045 Uiso 1 1 calc R U . . .
C11 C 0.3674(5) -0.2303(3) 0.8382(3) 0.0355(8) Uani 1 1 d . . . . .
H11A H 0.2910 -0.2446 0.8817 0.043 Uiso 1 1 calc R U . . .
C12 C 0.4595(5) -0.1253(3) 0.8559(3) 0.0296(7) Uani 1 1 d . . . . .
H12A H 0.4454 -0.0676 0.9111 0.036 Uiso 1 1 calc R U . . .
C13 C 0.8294(4) 0.0337(3) 0.9707(3) 0.0282(7) Uani 1 1 d . . . . .
C14 C 0.8132(5) -0.0443(4) 1.0579(3) 0.0384(8) Uani 1 1 d . . . . .
H14A H 0.7247 -0.1022 1.0383 0.046 Uiso 1 1 calc R U . . .
C15 C 0.9258(6) -0.0382(5) 1.1738(3) 0.0521(11) Uani 1 1 d . . . . .
H15A H 0.9141 -0.0918 1.2332 0.062 Uiso 1 1 calc R U . . .
C16 C 1.0547(6) 0.0458(5) 1.2025(4) 0.0540(12) Uani 1 1 d . . . . .
H16A H 1.1299 0.0513 1.2822 0.065 Uiso 1 1 calc R U . . .
C17 C 1.0740(6) 0.1215(4) 1.1156(4) 0.0498(11) Uani 1 1 d . . . . .
H17A H 1.1653 0.1771 1.1347 0.060 Uiso 1 1 calc R U . . .
C18 C 0.9603(5) 0.1166(3) 1.0003(3) 0.0396(9) Uani 1 1 d . . . . .
H18A H 0.9723 0.1704 0.9412 0.048 Uiso 1 1 calc R U . . .
C20 C 0.3900(5) 0.1846(3) 0.8133(3) 0.0288(7) Uani 1 1 d . . . . .
C21 C 0.4197(5) 0.3346(3) 0.6558(3) 0.0317(7) 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 C19 1.756(6) . ?
Mn1 C20 1.800(3) . ?
Mn1 C19' 1.82(3) . ?
Mn1 C21 1.841(4) . ?
Mn1 N2 2.075(2) . ?
Mn1 P1 2.2753(9) . ?
Mn1 Br1' 2.289(9) . ?
Mn1 Br1 2.5056(6) . ?
C19 O1 1.192(6) . ?
O1' C19' 1.27(3) . ?
P1 N1 1.696(3) . ?
P1 C7 1.819(3) . ?
P1 C13 1.829(3) . ?
O2 C20 1.142(4) . ?
O3 C21 1.130(5) . ?
N1 C1 1.380(4) . ?
N1 C6 1.465(5) . ?
N2 C1 1.350(4) . ?
N2 C5 1.352(4) . ?
C1 C2 1.404(4) . ?
C2 C3 1.371(5) . ?
C3 C4 1.385(6) . ?
C4 C5 1.375(5) . ?
C7 C12 1.394(4) . ?
C7 C8 1.394(4) . ?
C8 C9 1.385(5) . ?
C9 C10 1.383(5) . ?
C10 C11 1.379(5) . ?
C11 C12 1.379(5) . ?
C13 C18 1.386(5) . ?
C13 C14 1.388(5) . ?
C14 C15 1.390(5) . ?
C15 C16 1.382(7) . ?
C16 C17 1.378(7) . ?
C17 C18 1.388(6) . ?

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
C19 Mn1 C20 90.1(3) . . ?
C20 Mn1 C19' 92.4(19) . . ?
C19 Mn1 C21 91.3(3) . . ?
C20 Mn1 C21 89.85(15) . . ?
C19' Mn1 C21 88(2) . . ?
C19 Mn1 N2 92.8(2) . . ?
C20 Mn1 N2 173.10(13) . . ?
C19' Mn1 N2 85.0(19) . . ?
C21 Mn1 N2 96.38(13) . . ?
C19 Mn1 P1 95.7(2) . . ?
C20 Mn1 P1 92.72(11) . . ?
C19' Mn1 P1 85(2) . . ?
C21 Mn1 P1 172.55(11) . . ?
N2 Mn1 P1 80.73(8) . . ?
C20 Mn1 Br1' 90.63(18) . . ?
C19' Mn1 Br1' 172.5(19) . . ?
C21 Mn1 Br1' 85.5(3) . . ?
N2 Mn1 Br1' 92.81(17) . . ?
P1 Mn1 Br1' 101.4(2) . . ?
C19 Mn1 Br1 175.8(2) . . ?
C20 Mn1 Br1 92.17(11) . . ?
C21 Mn1 Br1 85.20(11) . . ?
N2 Mn1 Br1 85.43(7) . . ?
P1 Mn1 Br1 87.73(3) . . ?
O1 C19 Mn1 178.3(7) . . ?
O1' C19' Mn1 171(6) . . ?
N1 P1 C7 106.13(14) . . ?
N1 P1 C13 101.65(15) . . ?
C7 P1 C13 105.42(15) . . ?
N1 P1 Mn1 102.05(10) . . ?
C7 P1 Mn1 118.60(11) . . ?
C13 P1 Mn1 120.62(11) . . ?
C1 N1 C6 118.9(3) . . ?
C1 N1 P1 118.0(2) . . ?
C6 N1 P1 121.6(2) . . ?
C1 N2 C5 118.1(3) . . ?
C1 N2 Mn1 120.8(2) . . ?
C5 N2 Mn1 121.0(2) . . ?
N2 C1 N1 117.7(3) . . ?
N2 C1 C2 121.0(3) . . ?
N1 C1 C2 121.3(3) . . ?
C3 C2 C1 119.8(3) . . ?
C2 C3 C4 119.4(3) . . ?
C5 C4 C3 118.2(3) . . ?
N2 C5 C4 123.5(3) . . ?
C12 C7 C8 118.8(3) . . ?
C12 C7 P1 119.3(2) . . ?
C8 C7 P1 121.8(2) . . ?
C9 C8 C7 120.3(3) . . ?
C10 C9 C8 120.2(3) . . ?
C11 C10 C9 119.8(3) . . ?
C10 C11 C12 120.5(3) . . ?
C11 C12 C7 120.3(3) . . ?
C18 C13 C14 119.2(3) . . ?
C18 C13 P1 115.9(3) . . ?
C14 C13 P1 124.9(3) . . ?
C13 C14 C15 120.3(4) . . ?
C16 C15 C14 120.0(4) . . ?
C17 C16 C15 120.0(4) . . ?
C16 C17 C18 120.1(4) . . ?
C13 C18 C17 120.5(4) . . ?
O2 C20 Mn1 178.7(3) . . ?
O3 C21 Mn1 176.9(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
C7 P1 N1 C1 131.8(3) . . . . ?
C13 P1 N1 C1 -118.1(3) . . . . ?
Mn1 P1 N1 C1 7.0(3) . . . . ?
C7 P1 N1 C6 -62.4(3) . . . . ?
C13 P1 N1 C6 47.6(3) . . . . ?
Mn1 P1 N1 C6 172.7(3) . . . . ?
C5 N2 C1 N1 178.6(3) . . . . ?
Mn1 N2 C1 N1 -4.1(4) . . . . ?
C5 N2 C1 C2 0.5(5) . . . . ?
Mn1 N2 C1 C2 177.8(2) . . . . ?
C6 N1 C1 N2 -168.9(3) . . . . ?
P1 N1 C1 N2 -2.8(4) . . . . ?
C6 N1 C1 C2 9.2(5) . . . . ?
P1 N1 C1 C2 175.3(3) . . . . ?
N2 C1 C2 C3 -0.4(5) . . . . ?
N1 C1 C2 C3 -178.4(3) . . . . ?
C1 C2 C3 C4 0.7(6) . . . . ?
C2 C3 C4 C5 -1.0(6) . . . . ?
C1 N2 C5 C4 -0.9(5) . . . . ?
Mn1 N2 C5 C4 -178.2(3) . . . . ?
C3 C4 C5 N2 1.2(6) . . . . ?
N1 P1 C7 C12 173.6(3) . . . . ?
C13 P1 C7 C12 66.3(3) . . . . ?
Mn1 P1 C7 C12 -72.5(3) . . . . ?
N1 P1 C7 C8 -10.5(3) . . . . ?
C13 P1 C7 C8 -117.9(3) . . . . ?
Mn1 P1 C7 C8 103.4(3) . . . . ?
C12 C7 C8 C9 -2.7(5) . . . . ?
P1 C7 C8 C9 -178.5(3) . . . . ?
C7 C8 C9 C10 0.8(5) . . . . ?
C8 C9 C10 C11 1.2(6) . . . . ?
C9 C10 C11 C12 -1.4(6) . . . . ?
C10 C11 C12 C7 -0.5(6) . . . . ?
C8 C7 C12 C11 2.5(5) . . . . ?
P1 C7 C12 C11 178.4(3) . . . . ?
N1 P1 C13 C18 53.6(3) . . . . ?
C7 P1 C13 C18 164.1(3) . . . . ?
Mn1 P1 C13 C18 -58.1(3) . . . . ?
N1 P1 C13 C14 -126.7(3) . . . . ?
C7 P1 C13 C14 -16.1(4) . . . . ?
Mn1 P1 C13 C14 121.6(3) . . . . ?
C18 C13 C14 C15 0.8(6) . . . . ?
P1 C13 C14 C15 -178.9(3) . . . . ?
C13 C14 C15 C16 -0.1(6) . . . . ?
C14 C15 C16 C17 -1.6(7) . . . . ?
C15 C16 C17 C18 2.4(7) . . . . ?
C14 C13 C18 C17 0.0(6) . . . . ?
P1 C13 C18 C17 179.8(3) . . . . ?
C16 C17 C18 C13 -1.7(6) . . . . ?

_refine_diff_density_max         0.432
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.049

