# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_complex1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19.50 H27.50 Cl2 Mn N5 O1.50'
_chemical_formula_weight         481.80

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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.4242(2)
_cell_length_b                   9.17570(10)
_cell_length_c                   24.4086(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.9710(10)
_cell_angle_gamma                90.00
_cell_volume                     2292.00(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1002
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8513
_exptl_absorpt_correction_T_max  0.9365
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23831
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         30.04
_reflns_number_total             6697
_reflns_number_gt                4739
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0745P)²+1.0673P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6697
_refine_ls_number_parameters     298
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1463
_refine_ls_wR_factor_gt          0.1315
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.086
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.33821(4) 0.22350(4) 0.370920(15) 0.01853(11) Uani 1 1 d . . .
Cl1 Cl 0.33391(7) 0.46423(7) 0.32556(3) 0.02616(15) Uani 1 1 d . . .
Cl2 Cl 0.57425(6) 0.17173(7) 0.38947(3) 0.02752(16) Uani 1 1 d . . .
C11 C 0.4235(3) 0.1744(3) 0.23552(13) 0.0375(7) Uani 1 1 d . . .
H11A H 0.4902 0.1577 0.2134 0.045 Uiso 1 1 calc R . .
H11B H 0.4554 0.2478 0.2634 0.045 Uiso 1 1 calc R . .
C12 C 0.2994(4) 0.2275(4) 0.19825(13) 0.0398(7) Uani 1 1 d . . .
N3 N 0.2905(2) 0.0532(2) 0.29705(9) 0.0242(5) Uani 1 1 d . . .
C17 C -0.1065(3) 0.2153(4) 0.35959(15) 0.0429(8) Uani 1 1 d . . .
H17 H -0.1640 0.2421 0.3827 0.052 Uiso 1 1 calc R . .
C16 C -0.1518(3) 0.1494(4) 0.30905(15) 0.0429(8) Uani 1 1 d . . .
H16 H -0.2404 0.1301 0.2975 0.052 Uiso 1 1 calc R . .
N2 N 0.3209(2) 0.0459(2) 0.43566(9) 0.0237(5) Uani 1 1 d . . .
N1 N 0.3266(2) 0.3358(2) 0.45423(9) 0.0212(4) Uani 1 1 d . . .
N4 N 0.1898(3) 0.2383(3) 0.22868(10) 0.0315(5) Uani 1 1 d . . .
C15 C -0.0633(3) 0.1122(3) 0.27555(14) 0.0352(7) Uani 1 1 d . . .
H15 H -0.0917 0.0685 0.2410 0.042 Uiso 1 1 calc R . .
C4 C 0.3506(3) 0.2967(3) 0.55260(12) 0.0321(6) Uani 1 1 d . . .
H4A H 0.3579 0.2315 0.5822 0.038 Uiso 1 1 calc R . .
N5 N 0.1127(2) 0.2047(2) 0.34391(10) 0.0258(5) Uani 1 1 d . . .
C1 C 0.3268(3) 0.4795(3) 0.46398(11) 0.0252(5) Uani 1 1 d . . .
H1 H 0.3178 0.5427 0.4337 0.030 Uiso 1 1 calc R . .
C2 C 0.3397(3) 0.5382(3) 0.51684(12) 0.0299(6) Uani 1 1 d . . .
H2 H 0.3392 0.6386 0.5218 0.036 Uiso 1 1 calc R . .
C14 C 0.0672(3) 0.1410(3) 0.29433(12) 0.0278(6) Uani 1 1 d . . .
C8 C 0.3603(3) -0.1462(3) 0.36939(12) 0.0298(6) Uani 1 1 d . . .
H8A H 0.3710 -0.2507 0.3665 0.036 Uiso 1 1 calc R . .
H8B H 0.4442 -0.1010 0.3688 0.036 Uiso 1 1 calc R . .
C5 C 0.3365(3) 0.2461(3) 0.49845(11) 0.0239(5) Uani 1 1 d . . .
C6 C 0.3345(3) 0.0885(3) 0.48585(11) 0.0265(6) Uani 1 1 d . . .
H6 H 0.3432 0.0208 0.5147 0.032 Uiso 1 1 calc R . .
C7 C 0.3204(3) -0.1117(3) 0.42500(14) 0.0304(6) Uani 1 1 d . . .
C13 C 0.1697(3) 0.1072(3) 0.25963(12) 0.0279(6) Uani 1 1 d . . .
C10 C 0.3959(3) 0.0347(3) 0.26381(13) 0.0318(6) Uani 1 1 d . . .
H10A H 0.3700 -0.0400 0.2358 0.038 Uiso 1 1 calc R . .
H10B H 0.4752 0.0022 0.2883 0.038 Uiso 1 1 calc R . .
C3 C 0.3535(3) 0.4457(3) 0.56228(12) 0.0330(6) Uani 1 1 d . . .
H3 H 0.3644 0.4824 0.5984 0.040 Uiso 1 1 calc R . .
C9 C 0.2608(3) -0.0930(3) 0.31860(13) 0.0305(6) Uani 1 1 d . . .
H9A H 0.2568 -0.1638 0.2888 0.037 Uiso 1 1 calc R . .
H9B H 0.1752 -0.0893 0.3286 0.037 Uiso 1 1 calc R . .
C18 C 0.0265(3) 0.2410(4) 0.37556(14) 0.0379(7) Uani 1 1 d . . .
H18 H 0.0568 0.2855 0.4098 0.045 Uiso 1 1 calc R . .
O1 O 0.0090(4) 0.2841(4) 0.12762(15) 0.0835(10) Uani 1 1 d . . .
H1A H 0.0627 0.2844 0.1569 0.125 Uiso 1 1 calc R . .
C19 C -0.0190(6) 0.1390(6) 0.1101(3) 0.122(3) Uani 1 1 d . . .
H19A H 0.0556 0.0787 0.1236 0.183 Uiso 1 1 calc R . .
H19B H -0.0389 0.1353 0.0701 0.183 Uiso 1 1 calc R . .
H19C H -0.0926 0.1044 0.1248 0.183 Uiso 1 1 calc R . .
C20 C 0.0000 0.5000 0.0000 0.136(4) Uani 1 2 d SD . .
O2 O 0.0505(13) 0.3745(13) 0.0210(5) 0.157(5) Uani 0.50 1 d PD . .
H7A H 0.232(3) -0.146(3) 0.4231(12) 0.025(7) Uiso 1 1 d . . .
H7B H 0.372(3) -0.151(4) 0.4547(14) 0.033(8) Uiso 1 1 d . . .
H12A H 0.299(3) 0.333(4) 0.1765(14) 0.037(9) Uiso 1 1 d . . .
H12B H 0.260(3) 0.152(4) 0.1675(14) 0.041(9) Uiso 1 1 d . . .
H13 H 0.130(3) 0.038(3) 0.2297(12) 0.024(7) Uiso 1 1 d . . .
H4 H 0.204(3) 0.319(4) 0.2565(14) 0.033(8) Uiso 1 1 d . . .
H2A H 0.064(12) 0.359(7) 0.0595(12) 0.13(5) Uiso 0.50 1 d PD . .


_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 N2 2.301(2) . ?
Mn1 N1 2.303(2) . ?
Mn1 N5 2.324(2) . ?
Mn1 N3 2.366(2) . ?
Mn1 Cl2 2.4619(7) . ?
Mn1 Cl1 2.4674(7) . ?
C11 C10 1.510(4) . ?
C11 C12 1.513(5) . ?
C12 N4 1.480(4) . ?
N3 C13 1.493(3) . ?
N3 C9 1.494(3) . ?
N3 C10 1.495(4) . ?
C17 C16 1.374(5) . ?
C17 C18 1.387(4) . ?
C16 C15 1.387(5) . ?
N2 C6 1.268(4) . ?
N2 C7 1.469(3) . ?
N1 C1 1.340(3) . ?
N1 C5 1.345(3) . ?
N4 C13 1.456(4) . ?
C15 C14 1.376(4) . ?
C4 C5 1.382(4) . ?
C4 C3 1.387(4) . ?
N5 C18 1.334(4) . ?
N5 C14 1.346(4) . ?
C1 C2 1.381(4) . ?
C2 C3 1.382(4) . ?
C14 C13 1.516(4) . ?
C8 C7 1.527(4) . ?
C8 C9 1.536(4) . ?
C5 C6 1.478(4) . ?
O1 C19 1.412(6) . ?
C20 O2 1.327(10) 3_565 ?
C20 O2 1.327(10) . ?

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
N2 Mn1 N1 71.71(7) . . ?
N2 Mn1 N5 86.29(8) . . ?
N1 Mn1 N5 93.63(8) . . ?
N2 Mn1 N3 91.31(8) . . ?
N1 Mn1 N3 158.33(8) . . ?
N5 Mn1 N3 71.35(8) . . ?
N2 Mn1 Cl2 86.74(6) . . ?
N1 Mn1 Cl2 98.20(6) . . ?
N5 Mn1 Cl2 163.64(6) . . ?
N3 Mn1 Cl2 94.04(6) . . ?
N2 Mn1 Cl1 160.94(6) . . ?
N1 Mn1 Cl1 89.79(5) . . ?
N5 Mn1 Cl1 90.46(6) . . ?
N3 Mn1 Cl1 105.43(6) . . ?
Cl2 Mn1 Cl1 100.80(3) . . ?
C10 C11 C12 109.4(3) . . ?
N4 C12 C11 111.9(3) . . ?
C13 N3 C9 107.9(2) . . ?
C13 N3 C10 109.1(2) . . ?
C9 N3 C10 108.2(2) . . ?
C13 N3 Mn1 106.11(15) . . ?
C9 N3 Mn1 110.63(17) . . ?
C10 N3 Mn1 114.76(16) . . ?
C16 C17 C18 118.8(3) . . ?
C17 C16 C15 119.0(3) . . ?
C6 N2 C7 118.1(2) . . ?
C6 N2 Mn1 115.85(17) . . ?
C7 N2 Mn1 125.01(18) . . ?
C1 N1 C5 117.5(2) . . ?
C1 N1 Mn1 126.75(17) . . ?
C5 N1 Mn1 115.23(16) . . ?
C13 N4 C12 113.9(2) . . ?
C14 C15 C16 118.8(3) . . ?
C5 C4 C3 119.3(3) . . ?
C18 N5 C14 117.9(2) . . ?
C18 N5 Mn1 125.0(2) . . ?
C14 N5 Mn1 116.82(18) . . ?
N1 C1 C2 123.1(2) . . ?
C1 C2 C3 119.2(3) . . ?
N5 C14 C15 122.7(3) . . ?
N5 C14 C13 115.2(2) . . ?
C15 C14 C13 122.1(3) . . ?
C7 C8 C9 113.3(2) . . ?
N1 C5 C4 122.7(2) . . ?
N1 C5 C6 115.8(2) . . ?
C4 C5 C6 121.5(2) . . ?
N2 C6 C5 119.8(2) . . ?
N2 C7 C8 111.6(2) . . ?
N4 C13 N3 113.8(2) . . ?
N4 C13 C14 107.9(2) . . ?
N3 C13 C14 109.2(2) . . ?
N3 C10 C11 112.0(2) . . ?
C2 C3 C4 118.2(3) . . ?
N3 C9 C8 114.6(2) . . ?
N5 C18 C17 122.8(3) . . ?
O2 C20 O2 180.0(9) 3_565 . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.04
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.855
_refine_diff_density_min         -0.785
_refine_diff_density_rms         0.123

_database_code_depnum_ccdc_archive 'CCDC 962739'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cmapo51

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H44 Cl4 Mn2 N8'
_chemical_formula_weight         720.37

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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   19.2620(3)
_cell_length_b                   11.79600(1)
_cell_length_c                   17.1290(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 122.207(5)
_cell_angle_gamma                90.00
_cell_volume                     3293.09(20)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            Light-yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1496
_exptl_absorpt_coefficient_mu    1.122
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.720
_exptl_absorpt_correction_T_max  0.845
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10331
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         32.05
_reflns_number_total             5725
_reflns_number_gt                5238
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0293P)²+3.1977P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5725
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_ref         0.0710
_refine_ls_wR_factor_gt          0.0645
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.224701(9) 0.021873(14) 0.043339(11) 0.01431(5) Uani 1 1 d . . .
Cl1 Cl 0.146493(16) -0.13943(2) -0.072649(19) 0.02044(6) Uani 1 1 d . . .
Cl2 Cl 0.307386(16) 0.17982(2) 0.157728(18) 0.01988(6) Uani 1 1 d . . .
N1 N 0.10497(5) 0.11674(8) -0.02040(6) 0.01623(16) Uani 1 1 d . . .
N2 N 0.17422(6) -0.00663(8) 0.13333(6) 0.01685(16) Uani 1 1 d . . .
N4 N 0.26437(6) 0.06881(9) -0.05311(6) 0.01899(17) Uani 1 1 d . . .
H4A H 0.2372 0.0240 -0.1031 0.023 Uiso 1 1 calc R . .
H4B H 0.2477 0.1404 -0.0720 0.023 Uiso 1 1 calc R . .
N3 N 0.33006(6) -0.09634(8) 0.12131(6) 0.01694(16) Uani 1 1 d . . .
C6 C 0.11350(7) 0.05499(9) 0.11882(7) 0.01726(18) Uani 1 1 d . . .
C10 C 0.34994(7) -0.12079(10) 0.21565(8) 0.0218(2) Uani 1 1 d . . .
H10A H 0.3712 -0.0526 0.2528 0.026 Uiso 1 1 calc R . .
H10B H 0.3925 -0.1781 0.2432 0.026 Uiso 1 1 calc R . .
C1 C 0.06738(7) 0.16835(10) -0.10246(8) 0.01919(19) Uani 1 1 d . . .
H1 H 0.0913 0.1645 -0.1374 0.023 Uiso 1 1 calc R . .
C13 C 0.35252(7) 0.06223(11) -0.01977(8) 0.0226(2) Uani 1 1 d . . .
H13A H 0.3812 0.1238 0.0232 0.027 Uiso 1 1 calc R . .
H13B H 0.3592 0.0721 -0.0716 0.027 Uiso 1 1 calc R . .
C11 C 0.40526(7) -0.06544(11) 0.12340(8) 0.0219(2) Uani 1 1 d . . .
H11A H 0.4461 -0.1242 0.1557 0.026 Uiso 1 1 calc R . .
H11B H 0.4270 0.0044 0.1579 0.026 Uiso 1 1 calc R . .
C9 C 0.27541(7) -0.16219(10) 0.21687(8) 0.0233(2) Uani 1 1 d . . .
H9A H 0.2420 -0.2084 0.1624 0.028 Uiso 1 1 calc R . .
H9B H 0.2946 -0.2108 0.2702 0.028 Uiso 1 1 calc R . .
C5 C 0.06988(6) 0.12008(9) 0.03014(8) 0.01667(18) Uani 1 1 d . . .
C8 C 0.22103(7) -0.07068(11) 0.21961(8) 0.0218(2) Uani 1 1 d . . .
H8A H 0.1830 -0.1058 0.2331 0.026 Uiso 1 1 calc R . .
H8B H 0.2551 -0.0185 0.2694 0.026 Uiso 1 1 calc R . .
C2 C -0.00610(7) 0.22781(10) -0.13818(8) 0.0223(2) Uani 1 1 d . . .
H2 H -0.0308 0.2630 -0.1955 0.027 Uiso 1 1 calc R . .
C12 C 0.39134(7) -0.04980(11) 0.02769(9) 0.0241(2) Uani 1 1 d . . .
H12A H 0.4438 -0.0569 0.0328 0.029 Uiso 1 1 calc R . .
H12B H 0.3566 -0.1110 -0.0115 0.029 Uiso 1 1 calc R . .
C3 C -0.04107(7) 0.23288(11) -0.08577(9) 0.0245(2) Uani 1 1 d . . .
H3 H -0.0897 0.2726 -0.1072 0.029 Uiso 1 1 calc R . .
C4 C -0.00327(7) 0.17830(10) -0.00069(9) 0.0225(2) Uani 1 1 d . . .
H4 H -0.0264 0.1806 0.0350 0.027 Uiso 1 1 calc R . .
C7 C 0.08460(8) 0.06633(11) 0.18437(9) 0.0260(2) Uani 1 1 d . . .
H7A H 0.1181 0.0202 0.2378 0.039 Uiso 1 1 calc R . .
H7B H 0.0285 0.0419 0.1544 0.039 Uiso 1 1 calc R . .
H7C H 0.0886 0.1441 0.2028 0.039 Uiso 1 1 calc R . .
H3A H 0.3092(10) -0.1590(14) 0.0865(11) 0.022(4) Uiso 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 N3 2.2266(9) . ?
Mn1 N4 2.2284(9) . ?
Mn1 N2 2.2434(9) . ?
Mn1 N1 2.2536(9) . ?
Mn1 Cl2 2.5535(3) . ?
Mn1 Cl1 2.5781(3) . ?
N1 C1 1.3364(14) . ?
N1 C5 1.3534(14) . ?
N2 C6 1.2837(14) . ?
N2 C8 1.4654(14) . ?
N4 C13 1.4769(15) . ?
N3 C11 1.4754(14) . ?
N3 C10 1.4769(15) . ?
C6 C5 1.4975(16) . ?
C6 C7 1.5015(15) . ?
C10 C9 1.5270(17) . ?
C1 C2 1.3951(16) . ?
C13 C12 1.5226(18) . ?
C11 C12 1.5247(17) . ?
C9 C8 1.5222(17) . ?
C5 C4 1.3937(15) . ?
C2 C3 1.3812(18) . ?
C3 C4 1.3918(18) . ?

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
N3 Mn1 N4 92.13(4) . . ?
N3 Mn1 N2 94.83(3) . . ?
N4 Mn1 N2 172.83(4) . . ?
N3 Mn1 N1 166.36(3) . . ?
N4 Mn1 N1 100.61(3) . . ?
N2 Mn1 N1 72.60(3) . . ?
N3 Mn1 Cl2 90.02(3) . . ?
N4 Mn1 Cl2 93.87(3) . . ?
N2 Mn1 Cl2 84.47(2) . . ?
N1 Mn1 Cl2 93.91(2) . . ?
N3 Mn1 Cl1 88.37(3) . . ?
N4 Mn1 Cl1 84.40(3) . . ?
N2 Mn1 Cl1 97.45(3) . . ?
N1 Mn1 Cl1 88.07(2) . . ?
Cl2 Mn1 Cl1 177.588(11) . . ?
C1 N1 C5 118.96(9) . . ?
C1 N1 Mn1 125.22(7) . . ?
C5 N1 Mn1 115.82(7) . . ?
C6 N2 C8 119.64(9) . . ?
C6 N2 Mn1 117.77(7) . . ?
C8 N2 Mn1 120.74(7) . . ?
C13 N4 Mn1 118.56(7) . . ?
C11 N3 C10 110.06(9) . . ?
C11 N3 Mn1 115.41(7) . . ?
C10 N3 Mn1 113.61(7) . . ?
N2 C6 C5 116.58(9) . . ?
N2 C6 C7 124.63(11) . . ?
C5 C6 C7 118.79(10) . . ?
N3 C10 C9 112.33(9) . . ?
N1 C1 C2 123.00(11) . . ?
N4 C13 C12 112.85(10) . . ?
N3 C11 C12 113.33(9) . . ?
C8 C9 C10 116.17(10) . . ?
N1 C5 C4 121.37(10) . . ?
N1 C5 C6 115.62(9) . . ?
C4 C5 C6 122.98(10) . . ?
N2 C8 C9 113.47(9) . . ?
C3 C2 C1 117.97(11) . . ?
C13 C12 C11 115.72(10) . . ?
C2 C3 C4 119.75(11) . . ?
C3 C4 C5 118.93(11) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        32.05
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.065
_database_code_depnum_ccdc_archive 'CCDC 997081'
