# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

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

data_32043403_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1956316'
loop_
_audit_author_name
_audit_author_address
'Jesus Castro'
;Univ of Vigo
Spain
;
_audit_update_record             
;
2019-09-27 deposited with the CCDC.	2019-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H30 Cl2 Mn N4 O2 P2'
_chemical_formula_weight         546.26

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'
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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   13.4104(6)
_cell_length_b                   13.4995(6)
_cell_length_c                   14.4145(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.687(2)
_cell_angle_gamma                90
_cell_volume                     2545.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9883
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      28.30

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_F_000             1132
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.167
_exptl_absorpt_coefficient_mu    0.878
_shelx_estimated_absorpt_T_min   0.808
_shelx_estimated_absorpt_T_max   0.867

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6883
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS Inc.)'
# _exptl_absorpt_special_details    ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Incoatec high brillance I\muS microsource'
_diffrn_radiation_monochromator  'Incoatec HeliosTM multilayer optics'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24362
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.791
_diffrn_reflns_theta_max         28.328
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3182
_reflns_number_gt                2716
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXT 2018/2 (Sheldrick, 2018)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0383P)²+2.3663P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3182
_refine_ls_number_parameters     143
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0733
_refine_ls_wR_factor_gt          0.0694
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.500000 0.70686(2) 0.750000 0.01200(9) Uani 1 2 d S T P . .
Cl1 Cl 0.54067(3) 0.79343(3) 0.62274(3) 0.02978(12) Uani 1 1 d . . . . .
P1 P 0.28761(3) 0.55555(3) 0.69645(3) 0.01120(9) Uani 1 1 d . . . . .
O1 O 0.38317(8) 0.61203(7) 0.69419(7) 0.0139(2) Uani 1 1 d . . . . .
C11 C 0.31590(11) 0.47145(10) 0.79504(10) 0.0124(3) Uani 1 1 d . . . . .
C12 C 0.23728(12) 0.40961(11) 0.81039(11) 0.0164(3) Uani 1 1 d . . . . .
H12 H 0.171410 0.413460 0.769439 0.020 Uiso 1 1 calc R U . . .
C13 C 0.25536(13) 0.34276(11) 0.88522(11) 0.0187(3) Uani 1 1 d . . . . .
H13 H 0.201865 0.300905 0.895505 0.022 Uiso 1 1 calc R U . . .
C14 C 0.35142(13) 0.33693(11) 0.94505(11) 0.0189(3) Uani 1 1 d . . . . .
H14 H 0.363652 0.290983 0.996223 0.023 Uiso 1 1 calc R U . . .
C15 C 0.42973(12) 0.39798(12) 0.93043(11) 0.0192(3) Uani 1 1 d . . . . .
H15 H 0.495426 0.393764 0.971653 0.023 Uiso 1 1 calc R U . . .
C16 C 0.41237(12) 0.46539(11) 0.85558(10) 0.0165(3) Uani 1 1 d . . . . .
H16 H 0.466084 0.507193 0.845721 0.020 Uiso 1 1 calc R U . . .
N1 N 0.23323(9) 0.49398(9) 0.60175(9) 0.0159(3) Uani 1 1 d . . . . .
N2 N 0.18682(10) 0.62408(9) 0.69807(10) 0.0177(3) Uani 1 1 d . . . . .
C1 C 0.28228(13) 0.41914(11) 0.55483(11) 0.0203(3) Uani 1 1 d . . . . .
H1A H 0.237651 0.361066 0.540907 0.030 Uiso 1 1 calc R U . . .
H1B H 0.347326 0.399762 0.596541 0.030 Uiso 1 1 calc R U . . .
H1C H 0.295001 0.446061 0.495349 0.030 Uiso 1 1 calc R U . . .
C2 C 0.13178(12) 0.53055(12) 0.55608(11) 0.0207(3) Uani 1 1 d . . . . .
H2A H 0.085178 0.474725 0.532591 0.025 Uiso 1 1 calc R U . . .
H2B H 0.135623 0.574219 0.501799 0.025 Uiso 1 1 calc R U . . .
C3 C 0.09430(12) 0.58814(13) 0.63280(12) 0.0225(3) Uani 1 1 d . . . . .
H3A H 0.050509 0.644287 0.604564 0.027 Uiso 1 1 calc R U . . .
H3B H 0.054545 0.544598 0.666540 0.027 Uiso 1 1 calc R U . . .
C4 C 0.17560(14) 0.68163(13) 0.78044(13) 0.0259(4) Uani 1 1 d . . . . .
H4A H 0.135188 0.741175 0.759269 0.039 Uiso 1 1 calc R U . . .
H4B H 0.243272 0.700921 0.817149 0.039 Uiso 1 1 calc R U . . .
H4C H 0.140793 0.641573 0.820406 0.039 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 O1 2.0462(10) 2_656 ?
Mn1 O1 2.0463(10) . ?
Mn1 Cl1 2.3383(4) . ?
Mn1 Cl1 2.3384(4) 2_656 ?
P1 O1 1.4977(10) . ?
P1 N1 1.6275(13) . ?
P1 N2 1.6422(13) . ?
P1 C11 1.7932(14) . ?
C11 C16 1.395(2) . ?
C11 C12 1.400(2) . ?
C12 C13 1.386(2) . ?
C13 C14 1.386(2) . ?
C14 C15 1.387(2) . ?
C15 C16 1.392(2) . ?
N1 C1 1.451(2) . ?
N1 C2 1.4610(19) . ?
N2 C4 1.454(2) . ?
N2 C3 1.465(2) . ?
C2 C3 1.524(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Mn1 O1 102.55(6) 2_656 . ?
O1 Mn1 Cl1 109.31(3) 2_656 . ?
O1 Mn1 Cl1 107.13(3) . . ?
O1 Mn1 Cl1 107.13(3) 2_656 2_656 ?
O1 Mn1 Cl1 109.31(3) . 2_656 ?
Cl1 Mn1 Cl1 120.03(3) . 2_656 ?
O1 P1 N1 118.01(6) . . ?
O1 P1 N2 115.11(6) . . ?
N1 P1 N2 94.65(7) . . ?
O1 P1 C11 107.85(6) . . ?
N1 P1 C11 108.61(7) . . ?
N2 P1 C11 112.15(7) . . ?
P1 O1 Mn1 153.49(7) . . ?
C16 C11 C12 119.55(13) . . ?
C16 C11 P1 122.59(11) . . ?
C12 C11 P1 117.86(11) . . ?
C13 C12 C11 120.14(14) . . ?
C14 C13 C12 120.05(14) . . ?
C13 C14 C15 120.19(14) . . ?
C14 C15 C16 120.20(15) . . ?
C15 C16 C11 119.85(14) . . ?
C1 N1 C2 119.85(13) . . ?
C1 N1 P1 125.52(11) . . ?
C2 N1 P1 114.00(11) . . ?
C4 N2 C3 118.44(13) . . ?
C4 N2 P1 123.07(11) . . ?
C3 N2 P1 112.82(11) . . ?
N1 C2 C3 105.56(12) . . ?
N2 C3 C2 105.49(12) . . ?

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
N1 P1 O1 Mn1 174.68(13) . . . . ?
N2 P1 O1 Mn1 64.15(16) . . . . ?
C11 P1 O1 Mn1 -61.88(16) . . . . ?
O1 P1 C11 C16 0.34(14) . . . . ?
N1 P1 C11 C16 129.32(13) . . . . ?
N2 P1 C11 C16 -127.42(13) . . . . ?
O1 P1 C11 C12 -179.27(11) . . . . ?
N1 P1 C11 C12 -50.29(13) . . . . ?
N2 P1 C11 C12 52.97(13) . . . . ?
C16 C11 C12 C13 -0.1(2) . . . . ?
P1 C11 C12 C13 179.54(12) . . . . ?
C11 C12 C13 C14 0.0(2) . . . . ?
C12 C13 C14 C15 0.1(2) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C14 C15 C16 C11 -0.1(2) . . . . ?
C12 C11 C16 C15 0.1(2) . . . . ?
P1 C11 C16 C15 -179.47(12) . . . . ?
O1 P1 N1 C1 55.58(14) . . . . ?
N2 P1 N1 C1 177.28(13) . . . . ?
C11 P1 N1 C1 -67.47(14) . . . . ?
O1 P1 N1 C2 -115.23(11) . . . . ?
N2 P1 N1 C2 6.47(11) . . . . ?
C11 P1 N1 C2 121.72(11) . . . . ?
O1 P1 N2 C4 -71.30(14) . . . . ?
N1 P1 N2 C4 164.75(13) . . . . ?
C11 P1 N2 C4 52.49(14) . . . . ?
O1 P1 N2 C3 135.76(11) . . . . ?
N1 P1 N2 C3 11.81(12) . . . . ?
C11 P1 N2 C3 -100.45(11) . . . . ?
C1 N1 C2 C3 167.25(13) . . . . ?
P1 N1 C2 C3 -21.37(15) . . . . ?
C4 N2 C3 C2 -179.37(13) . . . . ?
P1 N2 C3 C2 -25.07(15) . . . . ?
N1 C2 C3 N2 27.65(16) . . . . ?

_refine_diff_density_max         0.408
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_32043404_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1956317'
loop_
_audit_author_name
_audit_author_address
'Jesus Castro'
;Univ of Vigo
Spain
;
_audit_update_record             
;
2019-09-27 deposited with the CCDC.	2019-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H30 Br2 Mn N4 O2 P2'

_chemical_formula_sum            'C20 H30 Br2 Mn N4 O2 P2'
_chemical_formula_weight         635.18

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   13.4668(6)
_cell_length_b                   13.7458(6)
_cell_length_c                   14.4342(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.192(2)
_cell_angle_gamma                90
_cell_volume                     2621.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9846
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      28.30

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_F_000             1276
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.074
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.065
_exptl_absorpt_coefficient_mu    3.698
_shelx_estimated_absorpt_T_min   0.771
_shelx_estimated_absorpt_T_max   0.795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6870
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Incoatec high brillance I\muS microsource'
_diffrn_radiation_monochromator  'Incoatec HeliosTM multilayer optics'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37967
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.739
_diffrn_reflns_theta_max         28.356
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3271
_reflns_number_gt                2873
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'

_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0213P)²+4.0817P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3271
_refine_ls_number_parameters     143
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0235
_refine_ls_wR_factor_ref         0.0531
_refine_ls_wR_factor_gt          0.0510
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.54431(2) 0.79207(2) 0.61495(2) 0.02598(7) Uani 1 1 d . . . . .
Mn1 Mn 0.500000 0.70155(2) 0.750000 0.01179(8) Uani 1 2 d S T P . .
P1 P 0.28878(3) 0.55496(3) 0.69781(3) 0.01159(9) Uani 1 1 d . . . . .
O1 O 0.38417(8) 0.61016(8) 0.69548(8) 0.0143(2) Uani 1 1 d . . . . .
N2 N 0.18938(10) 0.62293(11) 0.70163(10) 0.0180(3) Uani 1 1 d . . . . .
N1 N 0.23555(10) 0.49640(11) 0.60311(10) 0.0161(3) Uani 1 1 d . . . . .
C11 C 0.31518(12) 0.47034(12) 0.79404(11) 0.0127(3) Uani 1 1 d . . . . .
C12 C 0.40960(13) 0.46507(13) 0.85453(12) 0.0165(3) Uani 1 1 d . . . . .
H12 H 0.462782 0.507333 0.845628 0.020 Uiso 1 1 calc R U . . .
C13 C 0.42536(13) 0.39770(13) 0.92779(12) 0.0200(4) Uani 1 1 d . . . . .
H13 H 0.489395 0.394137 0.969151 0.024 Uiso 1 1 calc R U . . .
C14 C 0.34816(14) 0.33587(13) 0.94066(12) 0.0183(3) Uani 1 1 d . . . . .
H14 H 0.359509 0.289827 0.990691 0.022 Uiso 1 1 calc R U . . .
C15 C 0.25428(14) 0.34072(13) 0.88095(12) 0.0176(3) Uani 1 1 d . . . . .
H15 H 0.201501 0.298058 0.890051 0.021 Uiso 1 1 calc R U . . .
C16 C 0.23756(13) 0.40789(12) 0.80796(12) 0.0158(3) Uani 1 1 d . . . . .
H16 H 0.173113 0.411471 0.767286 0.019 Uiso 1 1 calc R U . . .
C1 C 0.28489(14) 0.42408(14) 0.55439(13) 0.0216(4) Uani 1 1 d . . . . .
H1A H 0.240297 0.367603 0.539138 0.032 Uiso 1 1 calc R U . . .
H1B H 0.348378 0.403678 0.595140 0.032 Uiso 1 1 calc R U . . .
H1C H 0.299310 0.452112 0.495988 0.032 Uiso 1 1 calc R U . . .
C2 C 0.13692(13) 0.53589(14) 0.55787(12) 0.0209(4) Uani 1 1 d . . . . .
H2A H 0.089937 0.482933 0.531706 0.025 Uiso 1 1 calc R U . . .
H2B H 0.144182 0.581056 0.506180 0.025 Uiso 1 1 calc R U . . .
C3 C 0.09842(13) 0.58942(14) 0.63617(13) 0.0233(4) Uani 1 1 d . . . . .
H3A H 0.055533 0.645321 0.610244 0.028 Uiso 1 1 calc R U . . .
H3B H 0.058170 0.545306 0.668660 0.028 Uiso 1 1 calc R U . . .
C4 C 0.17630(15) 0.67698(15) 0.78517(14) 0.0270(4) Uani 1 1 d . . . . .
H4A H 0.135585 0.735253 0.765924 0.041 Uiso 1 1 calc R U . . .
H4B H 0.242721 0.696178 0.821284 0.041 Uiso 1 1 calc R U . . .
H4C H 0.141799 0.635882 0.824538 0.041 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
Br1 Mn1 2.4811(3) . ?
Mn1 O1 2.0381(11) 2_656 ?
Mn1 O1 2.0382(11) . ?
P1 O1 1.4979(12) . ?
P1 N1 1.6279(14) . ?
P1 N2 1.6420(15) . ?
P1 C11 1.7936(16) . ?
N2 C4 1.456(2) . ?
N2 C3 1.468(2) . ?
N1 C1 1.451(2) . ?
N1 C2 1.466(2) . ?
C11 C16 1.397(2) . ?
C11 C12 1.398(2) . ?
C12 C13 1.391(2) . ?
C13 C14 1.383(2) . ?
C14 C15 1.387(2) . ?
C15 C16 1.386(2) . ?
C2 C3 1.521(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Mn1 O1 103.90(7) 2_656 . ?
O1 Mn1 Br1 106.77(3) 2_656 2_656 ?
O1 Mn1 Br1 109.25(3) . 2_656 ?
O1 Mn1 Br1 109.25(3) 2_656 . ?
O1 Mn1 Br1 106.77(3) . . ?
Br1 Mn1 Br1 119.801(17) 2_656 . ?
O1 P1 N1 118.12(7) . . ?
O1 P1 N2 114.89(7) . . ?
N1 P1 N2 94.62(8) . . ?
O1 P1 C11 107.70(7) . . ?
N1 P1 C11 108.56(8) . . ?
N2 P1 C11 112.54(8) . . ?
P1 O1 Mn1 154.01(8) . . ?
C4 N2 C3 118.23(15) . . ?
C4 N2 P1 123.27(12) . . ?
C3 N2 P1 112.56(12) . . ?
C1 N1 C2 119.89(14) . . ?
C1 N1 P1 125.26(12) . . ?
C2 N1 P1 113.84(12) . . ?
C16 C11 C12 119.59(15) . . ?
C16 C11 P1 117.94(12) . . ?
C12 C11 P1 122.47(12) . . ?
C13 C12 C11 119.71(16) . . ?
C14 C13 C12 120.24(16) . . ?
C13 C14 C15 120.36(16) . . ?
C16 C15 C14 119.90(16) . . ?
C15 C16 C11 120.20(16) . . ?
N1 C2 C3 104.96(14) . . ?
N2 C3 C2 105.52(14) . . ?

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
N1 P1 O1 Mn1 174.43(15) . . . . ?
N2 P1 O1 Mn1 64.03(18) . . . . ?
C11 P1 O1 Mn1 -62.25(18) . . . . ?
O1 P1 N2 C4 -72.46(16) . . . . ?
N1 P1 N2 C4 163.57(15) . . . . ?
C11 P1 N2 C4 51.28(17) . . . . ?
O1 P1 N2 C3 135.25(12) . . . . ?
N1 P1 N2 C3 11.28(13) . . . . ?
C11 P1 N2 C3 -101.01(13) . . . . ?
O1 P1 N1 C1 55.17(16) . . . . ?
N2 P1 N1 C1 176.62(15) . . . . ?
C11 P1 N1 C1 -67.73(16) . . . . ?
O1 P1 N1 C2 -113.28(12) . . . . ?
N2 P1 N1 C2 8.18(13) . . . . ?
C11 P1 N1 C2 123.83(12) . . . . ?
O1 P1 C11 C16 -177.75(13) . . . . ?
N1 P1 C11 C16 -48.77(15) . . . . ?
N2 P1 C11 C16 54.61(15) . . . . ?
O1 P1 C11 C12 2.24(16) . . . . ?
N1 P1 C11 C12 131.22(15) . . . . ?
N2 P1 C11 C12 -125.40(15) . . . . ?
C16 C11 C12 C13 0.1(3) . . . . ?
P1 C11 C12 C13 -179.89(14) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C14 C15 C16 C11 0.4(3) . . . . ?
C12 C11 C16 C15 -0.4(3) . . . . ?
P1 C11 C16 C15 179.58(13) . . . . ?
C1 N1 C2 C3 167.19(15) . . . . ?
P1 N1 C2 C3 -23.69(17) . . . . ?
C4 N2 C3 C2 -179.73(15) . . . . ?
P1 N2 C3 C2 -25.92(17) . . . . ?
N1 C2 C3 N2 29.49(18) . . . . ?

_refine_diff_density_max         0.687
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.066

