# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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. 
# 
#######################################################################

data_p21c
_database_code_depnum_ccdc_archive 'CCDC 1441057'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H32 B F4 Mn N4 O4'
_chemical_formula_weight         582.29

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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   P2(1)/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                   8.0671(15)
_cell_length_b                   15.486(3)
_cell_length_c                   21.277(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.059(4)
_cell_angle_gamma                90.00
_cell_volume                     2617.2(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9895
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      28.33

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1208
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.866
_exptl_absorpt_correction_T_max  0.918
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18716
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         28.33
_reflns_number_total             6427
_reflns_number_gt                5379
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0105P)²+7.1300P] 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         6427
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1176
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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
C1 C -0.3109(5) 0.6030(2) 0.44441(17) 0.0444(9) Uani 1 1 d . . .
H1 H -0.3909 0.5669 0.4159 0.067 Uiso 1 1 calc R . .
H2 H -0.3571 0.6613 0.4461 0.067 Uiso 1 1 calc R . .
H3 H -0.2911 0.5778 0.4873 0.067 Uiso 1 1 calc R . .
O1 O -0.1562(3) 0.60716(15) 0.42111(11) 0.0395(6) Uani 1 1 d . . .
C2 C -0.0807(4) 0.53016(19) 0.41241(13) 0.0275(6) Uani 1 1 d . . .
C3 C 0.0643(4) 0.53548(18) 0.38537(13) 0.0285(6) Uani 1 1 d . . .
H4 H 0.1047 0.5905 0.3753 0.034 Uiso 1 1 calc R . .
C4 C 0.1502(4) 0.46202(18) 0.37303(13) 0.0236(6) Uani 1 1 d . . .
H5 H 0.2476 0.4671 0.3538 0.028 Uiso 1 1 calc R . .
C5 C 0.0952(3) 0.37980(16) 0.38854(11) 0.0159(5) Uani 1 1 d . . .
O2 O 0.1868(2) 0.31136(11) 0.37770(8) 0.0154(3) Uani 1 1 d . . .
C6 C -0.0489(3) 0.37494(17) 0.41715(11) 0.0186(5) Uani 1 1 d . . .
C7 C -0.1348(4) 0.45077(19) 0.42919(13) 0.0248(6) Uani 1 1 d . . .
H6 H -0.2311 0.4469 0.4491 0.030 Uiso 1 1 calc R . .
C8 C -0.1009(3) 0.29392(17) 0.44152(11) 0.0177(5) Uani 1 1 d . . .
H7 H -0.1752 0.2961 0.4716 0.021 Uiso 1 1 calc R . .
N1 N -0.0536(3) 0.21943(13) 0.42533(9) 0.0143(4) Uani 1 1 d . . .
C9 C -0.0899(3) 0.14472(17) 0.46353(11) 0.0163(5) Uani 1 1 d . . .
H8 H -0.1306 0.0959 0.4349 0.020 Uiso 1 1 calc R . .
H9 H -0.1795 0.1600 0.4880 0.020 Uiso 1 1 calc R . .
C10 C 0.0681(3) 0.11782(17) 0.50935(11) 0.0185(5) Uani 1 1 d . . .
H10 H 0.0359 0.0751 0.5397 0.022 Uiso 1 1 calc R . .
H11 H 0.1135 0.1691 0.5344 0.022 Uiso 1 1 calc R . .
C11 C 0.2087(3) 0.07888(17) 0.47869(12) 0.0195(5) Uani 1 1 d . . .
H12 H 0.2989 0.0571 0.5126 0.023 Uiso 1 1 calc R . .
H13 H 0.1636 0.0293 0.4516 0.023 Uiso 1 1 calc R . .
N2 N 0.2809(3) 0.14296(14) 0.43919(10) 0.0154(4) Uani 1 1 d . . .
H14 H 0.321(4) 0.186(2) 0.4640(16) 0.025(8) Uiso 1 1 d . . .
C12 C 0.4252(3) 0.10676(16) 0.41355(11) 0.0160(5) Uani 1 1 d . . .
H15 H 0.3920 0.0521 0.3906 0.019 Uiso 1 1 calc R . .
H16 H 0.5195 0.0944 0.4489 0.019 Uiso 1 1 calc R . .
C13 C 0.4793(3) 0.17217(16) 0.36845(12) 0.0159(5) Uani 1 1 d . . .
H17 H 0.5087 0.2274 0.3911 0.019 Uiso 1 1 calc R . .
H18 H 0.5798 0.1509 0.3523 0.019 Uiso 1 1 calc R . .
N3 N 0.3390(3) 0.18563(13) 0.31462(10) 0.0144(4) Uani 1 1 d . . .
H19 H 0.325(4) 0.136(2) 0.2933(15) 0.023(8) Uiso 1 1 d . . .
C14 C 0.3724(3) 0.25660(16) 0.27217(12) 0.0171(5) Uani 1 1 d . . .
H20 H 0.4805 0.2457 0.2576 0.021 Uiso 1 1 calc R . .
H21 H 0.3830 0.3115 0.2964 0.021 Uiso 1 1 calc R . .
C15 C 0.2328(3) 0.26517(16) 0.21440(11) 0.0169(5) Uani 1 1 d . . .
H22 H 0.2108 0.2077 0.1943 0.020 Uiso 1 1 calc R . .
H23 H 0.2720 0.3036 0.1828 0.020 Uiso 1 1 calc R . .
C16 C 0.0679(3) 0.30091(17) 0.22991(11) 0.0169(5) Uani 1 1 d . . .
H24 H 0.0906 0.3540 0.2559 0.020 Uiso 1 1 calc R . .
H25 H -0.0092 0.3159 0.1899 0.020 Uiso 1 1 calc R . .
N4 N -0.0113(2) 0.23524(13) 0.26554(9) 0.0137(4) Uani 1 1 d . . .
C17 C -0.1389(3) 0.19526(16) 0.23440(11) 0.0137(4) Uani 1 1 d . . .
H26 H -0.1854 0.2156 0.1930 0.016 Uiso 1 1 calc R . .
C18 C -0.2165(3) 0.12077(15) 0.25870(11) 0.0129(4) Uani 1 1 d . . .
C19 C -0.3794(3) 0.09750(16) 0.22857(11) 0.0146(4) Uani 1 1 d . . .
H27 H -0.4338 0.1296 0.1928 0.018 Uiso 1 1 calc R . .
C20 C -0.4615(3) 0.02813(16) 0.25057(11) 0.0150(5) Uani 1 1 d . . .
O3 O -0.6266(2) 0.01659(12) 0.22181(9) 0.0213(4) Uani 1 1 d . . .
C21 C -0.7162(3) -0.05373(18) 0.24388(13) 0.0236(6) Uani 1 1 d . . .
H28 H -0.6594 -0.1081 0.2375 0.035 Uiso 1 1 calc R . .
H29 H -0.8315 -0.0551 0.2199 0.035 Uiso 1 1 calc R . .
H30 H -0.7191 -0.0461 0.2894 0.035 Uiso 1 1 calc R . .
C22 C -0.3771(3) -0.02237(15) 0.30023(11) 0.0151(5) Uani 1 1 d . . .
H31 H -0.4322 -0.0703 0.3154 0.018 Uiso 1 1 calc R . .
C23 C -0.2123(3) -0.00255(15) 0.32759(11) 0.0146(4) Uani 1 1 d . . .
H32 H -0.1542 -0.0392 0.3599 0.017 Uiso 1 1 calc R . .
C24 C -0.1298(3) 0.06997(15) 0.30880(11) 0.0128(4) Uani 1 1 d . . .
O4 O 0.0270(2) 0.08792(11) 0.33830(8) 0.0136(3) Uani 1 1 d . . .
Mn1 Mn 0.10606(4) 0.20009(2) 0.357993(16) 0.01179(9) Uani 1 1 d . . .
B1 B -0.3764(4) 0.3064(2) 0.08350(14) 0.0231(6) Uani 1 1 d . . .
F1 F -0.3838(4) 0.39336(14) 0.07458(11) 0.0638(8) Uani 1 1 d . . .
F2 F -0.4526(2) 0.26577(13) 0.02701(9) 0.0358(4) Uani 1 1 d . . .
F3 F -0.4499(2) 0.28148(14) 0.13473(9) 0.0381(5) Uani 1 1 d . . .
F4 F -0.2106(3) 0.2789(2) 0.09424(9) 0.0610(8) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.422(5) . ?
C1 H1 0.9800 . ?
C1 H2 0.9800 . ?
C1 H3 0.9800 . ?
O1 C2 1.366(3) . ?
C2 C7 1.373(4) . ?
C2 C3 1.393(5) . ?
C3 C4 1.381(4) . ?
C3 H4 0.9500 . ?
C4 C5 1.407(4) . ?
C4 H5 0.9500 . ?
C5 O2 1.335(3) . ?
C5 C6 1.405(4) . ?
O2 Mn1 1.8639(18) . ?
C6 C7 1.409(4) . ?
C6 C8 1.448(4) . ?
C7 H6 0.9500 . ?
C8 N1 1.281(3) . ?
C8 H7 0.9500 . ?
N1 C9 1.472(3) . ?
N1 Mn1 2.109(2) . ?
C9 C10 1.522(3) . ?
C9 H8 0.9900 . ?
C9 H9 0.9900 . ?
C10 C11 1.528(4) . ?
C10 H10 0.9900 . ?
C10 H11 0.9900 . ?
C11 N2 1.484(3) . ?
C11 H12 0.9900 . ?
C11 H13 0.9900 . ?
N2 C12 1.479(3) . ?
N2 Mn1 2.215(2) . ?
N2 H14 0.88(3) . ?
C12 C13 1.511(3) . ?
C12 H15 0.9900 . ?
C12 H16 0.9900 . ?
C13 N3 1.477(3) . ?
C13 H17 0.9900 . ?
C13 H18 0.9900 . ?
N3 C14 1.477(3) . ?
N3 Mn1 2.245(2) . ?
N3 H19 0.89(3) . ?
C14 C15 1.521(3) . ?
C14 H20 0.9900 . ?
C14 H21 0.9900 . ?
C15 C16 1.529(3) . ?
C15 H22 0.9900 . ?
C15 H23 0.9900 . ?
C16 N4 1.479(3) . ?
C16 H24 0.9900 . ?
C16 H25 0.9900 . ?
N4 C17 1.282(3) . ?
N4 Mn1 2.101(2) . ?
C17 C18 1.450(3) . ?
C17 H26 0.9500 . ?
C18 C19 1.405(3) . ?
C18 C24 1.409(3) . ?
C19 C20 1.385(3) . ?
C19 H27 0.9500 . ?
C20 O3 1.377(3) . ?
C20 C22 1.393(3) . ?
O3 C21 1.431(3) . ?
C21 H28 0.9800 . ?
C21 H29 0.9800 . ?
C21 H30 0.9800 . ?
C22 C23 1.389(3) . ?
C22 H31 0.9500 . ?
C23 C24 1.399(3) . ?
C23 H32 0.9500 . ?
C24 O4 1.339(3) . ?
O4 Mn1 1.8727(17) . ?
B1 F1 1.360(4) . ?
B1 F3 1.384(3) . ?
B1 F4 1.384(4) . ?
B1 F2 1.400(4) . ?

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 C1 H1 109.5 . . ?
O1 C1 H2 109.5 . . ?
H1 C1 H2 109.5 . . ?
O1 C1 H3 109.5 . . ?
H1 C1 H3 109.5 . . ?
H2 C1 H3 109.5 . . ?
C2 O1 C1 116.5(3) . . ?
O1 C2 C7 125.2(3) . . ?
O1 C2 C3 115.5(3) . . ?
C7 C2 C3 119.2(3) . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H4 119.5 . . ?
C2 C3 H4 119.5 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H5 119.6 . . ?
C5 C4 H5 119.6 . . ?
O2 C5 C6 123.9(2) . . ?
O2 C5 C4 118.1(2) . . ?
C6 C5 C4 118.0(2) . . ?
C5 O2 Mn1 126.17(16) . . ?
C5 C6 C7 120.3(2) . . ?
C5 C6 C8 121.0(2) . . ?
C7 C6 C8 118.3(2) . . ?
C2 C7 C6 120.7(3) . . ?
C2 C7 H6 119.7 . . ?
C6 C7 H6 119.7 . . ?
N1 C8 C6 124.4(2) . . ?
N1 C8 H7 117.8 . . ?
C6 C8 H7 117.8 . . ?
C8 N1 C9 117.5(2) . . ?
C8 N1 Mn1 123.82(17) . . ?
C9 N1 Mn1 117.87(15) . . ?
N1 C9 C10 110.1(2) . . ?
N1 C9 H8 109.6 . . ?
C10 C9 H8 109.6 . . ?
N1 C9 H9 109.6 . . ?
C10 C9 H9 109.6 . . ?
H8 C9 H9 108.2 . . ?
C9 C10 C11 115.8(2) . . ?
C9 C10 H10 108.3 . . ?
C11 C10 H10 108.3 . . ?
C9 C10 H11 108.3 . . ?
C11 C10 H11 108.3 . . ?
H10 C10 H11 107.4 . . ?
N2 C11 C10 111.8(2) . . ?
N2 C11 H12 109.2 . . ?
C10 C11 H12 109.2 . . ?
N2 C11 H13 109.2 . . ?
C10 C11 H13 109.2 . . ?
H12 C11 H13 107.9 . . ?
C12 N2 C11 111.6(2) . . ?
C12 N2 Mn1 107.38(14) . . ?
C11 N2 Mn1 116.71(15) . . ?
C12 N2 H14 106(2) . . ?
C11 N2 H14 108(2) . . ?
Mn1 N2 H14 106(2) . . ?
N2 C12 C13 108.2(2) . . ?
N2 C12 H15 110.1 . . ?
C13 C12 H15 110.1 . . ?
N2 C12 H16 110.1 . . ?
C13 C12 H16 110.1 . . ?
H15 C12 H16 108.4 . . ?
N3 C13 C12 108.68(19) . . ?
N3 C13 H17 110.0 . . ?
C12 C13 H17 110.0 . . ?
N3 C13 H18 110.0 . . ?
C12 C13 H18 110.0 . . ?
H17 C13 H18 108.3 . . ?
C14 N3 C13 112.49(19) . . ?
C14 N3 Mn1 115.61(15) . . ?
C13 N3 Mn1 106.15(14) . . ?
C14 N3 H19 111(2) . . ?
C13 N3 H19 107(2) . . ?
Mn1 N3 H19 105(2) . . ?
N3 C14 C15 111.8(2) . . ?
N3 C14 H20 109.3 . . ?
C15 C14 H20 109.3 . . ?
N3 C14 H21 109.3 . . ?
C15 C14 H21 109.3 . . ?
H20 C14 H21 107.9 . . ?
C14 C15 C16 114.0(2) . . ?
C14 C15 H22 108.8 . . ?
C16 C15 H22 108.8 . . ?
C14 C15 H23 108.8 . . ?
C16 C15 H23 108.8 . . ?
H22 C15 H23 107.7 . . ?
N4 C16 C15 109.4(2) . . ?
N4 C16 H24 109.8 . . ?
C15 C16 H24 109.8 . . ?
N4 C16 H25 109.8 . . ?
C15 C16 H25 109.8 . . ?
H24 C16 H25 108.2 . . ?
C17 N4 C16 116.6(2) . . ?
C17 N4 Mn1 123.29(16) . . ?
C16 N4 Mn1 119.58(15) . . ?
N4 C17 C18 123.9(2) . . ?
N4 C17 H26 118.1 . . ?
C18 C17 H26 118.1 . . ?
C19 C18 C24 120.2(2) . . ?
C19 C18 C17 118.0(2) . . ?
C24 C18 C17 121.7(2) . . ?
C20 C19 C18 120.6(2) . . ?
C20 C19 H27 119.7 . . ?
C18 C19 H27 119.7 . . ?
O3 C20 C19 115.6(2) . . ?
O3 C20 C22 124.8(2) . . ?
C19 C20 C22 119.5(2) . . ?
C20 O3 C21 117.3(2) . . ?
O3 C21 H28 109.5 . . ?
O3 C21 H29 109.5 . . ?
H28 C21 H29 109.5 . . ?
O3 C21 H30 109.5 . . ?
H28 C21 H30 109.5 . . ?
H29 C21 H30 109.5 . . ?
C23 C22 C20 119.9(2) . . ?
C23 C22 H31 120.0 . . ?
C20 C22 H31 120.0 . . ?
C22 C23 C24 121.7(2) . . ?
C22 C23 H32 119.1 . . ?
C24 C23 H32 119.1 . . ?
O4 C24 C23 119.4(2) . . ?
O4 C24 C18 122.8(2) . . ?
C23 C24 C18 117.8(2) . . ?
C24 O4 Mn1 123.67(15) . . ?
O2 Mn1 O4 179.46(8) . . ?
O2 Mn1 N4 93.09(8) . . ?
O4 Mn1 N4 87.16(8) . . ?
O2 Mn1 N1 86.96(8) . . ?
O4 Mn1 N1 93.39(8) . . ?
N4 Mn1 N1 111.75(8) . . ?
O2 Mn1 N2 92.51(8) . . ?
O4 Mn1 N2 87.11(8) . . ?
N4 Mn1 N2 162.84(8) . . ?
N1 Mn1 N2 84.73(8) . . ?
O2 Mn1 N3 84.25(8) . . ?
O4 Mn1 N3 95.30(8) . . ?
N4 Mn1 N3 85.05(8) . . ?
N1 Mn1 N3 161.46(8) . . ?
N2 Mn1 N3 79.39(8) . . ?
F1 B1 F3 111.8(3) . . ?
F1 B1 F4 110.2(3) . . ?
F3 B1 F4 108.6(2) . . ?
F1 B1 F2 108.9(2) . . ?
F3 B1 F2 111.5(2) . . ?
F4 B1 F2 105.7(3) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.989
_refine_diff_density_min         -0.568
_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_p21c
_database_code_depnum_ccdc_archive 'CCDC 1441058'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H32 B F4 Mn N4 O4'
_chemical_formula_weight         582.29

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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   P2(1)/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                   8.1403(15)
_cell_length_b                   15.644(3)
_cell_length_c                   21.581(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.709(4)
_cell_angle_gamma                90.00
_cell_volume                     2708.9(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9773
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      28.24

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1208
_exptl_absorpt_coefficient_mu    0.552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.870
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17663
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         28.14
_reflns_number_total             5989
_reflns_number_gt                4969
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0378P)²+11.0152P] 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         5989
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_gt           0.0897
_refine_ls_wR_factor_ref         0.2147
_refine_ls_wR_factor_gt          0.2083
_refine_ls_goodness_of_fit_ref   1.237
_refine_ls_restrained_S_all      1.237
_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
C1 C 1.2071(8) -0.0539(5) 0.2561(4) 0.0665(19) Uani 1 1 d . . .
H1 H 1.1513 -0.1078 0.2628 0.100 Uiso 1 1 calc R . .
H2 H 1.3207 -0.0545 0.2801 0.100 Uiso 1 1 calc R . .
H3 H 1.2115 -0.0471 0.2113 0.100 Uiso 1 1 calc R . .
O1 O 1.1166(5) 0.0157(3) 0.2769(2) 0.0616(12) Uani 1 1 d . . .
C2 C 0.9538(6) 0.0281(3) 0.2477(2) 0.0383(11) Uani 1 1 d . . .
C3 C 0.8725(7) -0.0211(3) 0.1984(2) 0.0387(11) Uani 1 1 d . . .
H7 H 0.9272 -0.0687 0.1836 0.046 Uiso 1 1 calc R . .
C4 C 0.7110(7) -0.0005(3) 0.1709(2) 0.0374(11) Uani 1 1 d . . .
H8 H 0.6544 -0.0363 0.1387 0.045 Uiso 1 1 calc R . .
C5 C 0.6288(6) 0.0715(3) 0.1893(2) 0.0291(9) Uani 1 1 d . . .
C6 C 0.7136(6) 0.1204(3) 0.2397(2) 0.0293(9) Uani 1 1 d . . .
C7 C 0.8732(6) 0.0965(3) 0.2691(2) 0.0367(11) Uani 1 1 d . . .
H9 H 0.9269 0.1279 0.3044 0.044 Uiso 1 1 calc R . .
O2 O 0.4746(4) 0.0897(2) 0.16022(15) 0.0344(7) Uani 1 1 d . . .
C8 C 0.6352(6) 0.1939(3) 0.2637(2) 0.0335(10) Uani 1 1 d . . .
H10 H 0.6794 0.2132 0.3049 0.040 Uiso 1 1 calc R . .
N1 N 0.5108(5) 0.2344(2) 0.23317(18) 0.0332(9) Uani 1 1 d . . .
C9 C 0.4308(7) 0.2990(3) 0.2687(2) 0.0425(12) Uani 1 1 d . . .
H15 H 0.4099 0.3520 0.2435 0.051 Uiso 1 1 calc R . .
H16 H 0.5059 0.3130 0.3084 0.051 Uiso 1 1 calc R . .
C10 C 0.2674(7) 0.2641(4) 0.2830(3) 0.0471(13) Uani 1 1 d . . .
H17 H 0.2272 0.3022 0.3139 0.057 Uiso 1 1 calc R . .
H18 H 0.2882 0.2072 0.3029 0.057 Uiso 1 1 calc R . .
C11 C 0.1308(7) 0.2555(3) 0.2258(3) 0.0466(13) Uani 1 1 d . . .
H19 H 0.0234 0.2441 0.2400 0.056 Uiso 1 1 calc R . .
H20 H 0.1201 0.3101 0.2023 0.056 Uiso 1 1 calc R . .
N2 N 0.1655(5) 0.1856(3) 0.1834(2) 0.0377(9) Uani 1 1 d . . .
C12 C 0.0280(6) 0.1717(4) 0.1309(3) 0.0445(12) Uani 1 1 d . . .
H21 H -0.0025 0.2264 0.1088 0.053 Uiso 1 1 calc R . .
H22 H -0.0710 0.1500 0.1470 0.053 Uiso 1 1 calc R . .
C13 C 0.0814(7) 0.1078(4) 0.0858(3) 0.0459(13) Uani 1 1 d . . .
H23 H 0.1141 0.0534 0.1080 0.055 Uiso 1 1 calc R . .
H24 H -0.0120 0.0960 0.0512 0.055 Uiso 1 1 calc R . .
N3 N 0.2239(5) 0.1436(3) 0.0605(2) 0.0369(9) Uani 1 1 d . . .
C14 C 0.2979(7) 0.0807(4) 0.0218(3) 0.0483(14) Uani 1 1 d . . .
H25 H 0.2096 0.0581 -0.0114 0.058 Uiso 1 1 calc R . .
H26 H 0.3442 0.0322 0.0486 0.058 Uiso 1 1 calc R . .
C15 C 0.4344(7) 0.1201(4) -0.0085(2) 0.0488(14) Uani 1 1 d . . .
H27 H 0.3883 0.1711 -0.0325 0.059 Uiso 1 1 calc R . .
H28 H 0.4662 0.0786 -0.0390 0.059 Uiso 1 1 calc R . .
C16 C 0.5920(7) 0.1468(3) 0.0362(2) 0.0420(12) Uani 1 1 d . . .
H29 H 0.6334 0.0984 0.0641 0.050 Uiso 1 1 calc R . .
H30 H 0.6800 0.1627 0.0118 0.050 Uiso 1 1 calc R . .
N4 N 0.5544(5) 0.2205(3) 0.07448(18) 0.0348(9) Uani 1 1 d . . .
C17 C 0.6019(7) 0.2943(4) 0.0588(2) 0.0436(12) Uani 1 1 d . . .
H11 H 0.6757 0.2966 0.0291 0.052 Uiso 1 1 calc R . .
C18 C 0.5506(7) 0.3747(3) 0.0833(2) 0.0435(12) Uani 1 1 d . . .
C19 C 0.6351(9) 0.4504(4) 0.0710(3) 0.0603(17) Uani 1 1 d . . .
H12 H 0.7307 0.4468 0.0512 0.072 Uiso 1 1 calc R . .
C20 C 0.5800(11) 0.5285(4) 0.0873(3) 0.071(2) Uani 1 1 d . . .
O3 O 0.6537(10) 0.6052(3) 0.0784(3) 0.104(2) Uani 1 1 d . . .
C21 C 0.8048(15) 0.6021(6) 0.0555(5) 0.119(4) Uani 1 1 d . . .
H4 H 0.8852 0.5675 0.0838 0.178 Uiso 1 1 calc R . .
H5 H 0.8486 0.6602 0.0533 0.178 Uiso 1 1 calc R . .
H6 H 0.7863 0.5766 0.0134 0.178 Uiso 1 1 calc R . .
C22 C 0.4391(12) 0.5337(4) 0.1144(3) 0.073(2) Uani 1 1 d . . .
H13 H 0.4002 0.5881 0.1250 0.088 Uiso 1 1 calc R . .
C23 C 0.3530(10) 0.4612(4) 0.1263(3) 0.0597(17) Uani 1 1 d . . .
H14 H 0.2553 0.4662 0.1447 0.072 Uiso 1 1 calc R . .
C24 C 0.4089(7) 0.3796(3) 0.1114(2) 0.0394(11) Uani 1 1 d . . .
O4 O 0.3178(4) 0.3121(2) 0.12220(16) 0.0394(8) Uani 1 1 d . . .
B1 B 0.8845(11) 0.1953(6) -0.0868(4) 0.0616(19) Uani 1 1 d . . .
F1 F 0.9437(8) 0.2171(4) -0.1390(3) 0.128(2) Uani 1 1 d . . .
F2 F 0.9507(8) 0.2294(4) -0.0298(3) 0.124(2) Uani 1 1 d . . .
F3 F 0.7335(10) 0.2281(8) -0.0934(3) 0.225(6) Uani 1 1 d . . .
F4 F 0.8601(16) 0.1146(4) -0.0794(4) 0.207(5) Uani 1 1 d . . .
Mn1 Mn 0.39684(9) 0.20119(4) 0.14094(3) 0.0293(2) Uani 1 1 d . . .
H31 H 0.190(8) 0.182(4) 0.040(3) 0.050(19) Uiso 1 1 d . . .
H32 H 0.178(8) 0.139(4) 0.201(3) 0.050(17) 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
C1 O1 1.428(7) . ?
C1 H1 0.9800 . ?
C1 H2 0.9800 . ?
C1 H3 0.9800 . ?
O1 C2 1.382(6) . ?
C2 C7 1.374(7) . ?
C2 C3 1.388(7) . ?
C3 C4 1.385(7) . ?
C3 H7 0.9500 . ?
C4 C5 1.401(6) . ?
C4 H8 0.9500 . ?
C5 O2 1.336(6) . ?
C5 C6 1.410(6) . ?
C6 C7 1.398(7) . ?
C6 C8 1.452(6) . ?
C7 H9 0.9500 . ?
O2 Mn1 1.878(3) . ?
C8 N1 1.280(6) . ?
C8 H10 0.9500 . ?
N1 C9 1.483(6) . ?
N1 Mn1 2.114(4) . ?
C9 C10 1.518(8) . ?
C9 H15 0.9900 . ?
C9 H16 0.9900 . ?
C10 C11 1.521(8) . ?
C10 H17 0.9900 . ?
C10 H18 0.9900 . ?
C11 N2 1.484(7) . ?
C11 H19 0.9900 . ?
C11 H20 0.9900 . ?
N2 C12 1.468(7) . ?
N2 Mn1 2.242(4) . ?
N2 H32 0.83(6) . ?
C12 C13 1.509(8) . ?
C12 H21 0.9900 . ?
C12 H22 0.9900 . ?
C13 N3 1.474(7) . ?
C13 H23 0.9900 . ?
C13 H24 0.9900 . ?
N3 C14 1.483(7) . ?
N3 Mn1 2.232(4) . ?
N3 H31 0.77(6) . ?
C14 C15 1.512(8) . ?
C14 H25 0.9900 . ?
C14 H26 0.9900 . ?
C15 C16 1.528(8) . ?
C15 H27 0.9900 . ?
C15 H28 0.9900 . ?
C16 N4 1.479(6) . ?
C16 H29 0.9900 . ?
C16 H30 0.9900 . ?
N4 C17 1.281(7) . ?
N4 Mn1 2.101(4) . ?
C17 C18 1.453(8) . ?
C17 H11 0.9500 . ?
C18 C24 1.392(8) . ?
C18 C19 1.416(8) . ?
C19 C20 1.369(10) . ?
C19 H12 0.9500 . ?
C20 O3 1.370(7) . ?
C20 C22 1.374(11) . ?
O3 C21 1.402(13) . ?
C21 H4 0.9800 . ?
C21 H5 0.9800 . ?
C21 H6 0.9800 . ?
C22 C23 1.381(9) . ?
C22 H13 0.9500 . ?
C23 C24 1.410(7) . ?
C23 H14 0.9500 . ?
C24 O4 1.333(6) . ?
O4 Mn1 1.871(3) . ?
B1 F4 1.291(10) . ?
B1 F3 1.318(11) . ?
B1 F1 1.342(9) . ?
B1 F2 1.366(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
O1 C1 H1 109.5 . . ?
O1 C1 H2 109.5 . . ?
H1 C1 H2 109.5 . . ?
O1 C1 H3 109.5 . . ?
H1 C1 H3 109.5 . . ?
H2 C1 H3 109.5 . . ?
C2 O1 C1 118.1(5) . . ?
C7 C2 O1 115.6(5) . . ?
C7 C2 C3 119.8(5) . . ?
O1 C2 C3 124.6(5) . . ?
C4 C3 C2 119.6(5) . . ?
C4 C3 H7 120.2 . . ?
C2 C3 H7 120.2 . . ?
C3 C4 C5 122.0(4) . . ?
C3 C4 H8 119.0 . . ?
C5 C4 H8 119.0 . . ?
O2 C5 C4 119.6(4) . . ?
O2 C5 C6 123.0(4) . . ?
C4 C5 C6 117.3(4) . . ?
C7 C6 C5 120.1(4) . . ?
C7 C6 C8 118.7(4) . . ?
C5 C6 C8 121.2(4) . . ?
C2 C7 C6 121.0(4) . . ?
C2 C7 H9 119.5 . . ?
C6 C7 H9 119.5 . . ?
C5 O2 Mn1 123.9(3) . . ?
N1 C8 C6 124.4(4) . . ?
N1 C8 H10 117.8 . . ?
C6 C8 H10 117.8 . . ?
C8 N1 C9 116.7(4) . . ?
C8 N1 Mn1 123.1(3) . . ?
C9 N1 Mn1 119.5(3) . . ?
N1 C9 C10 109.6(4) . . ?
N1 C9 H15 109.7 . . ?
C10 C9 H15 109.7 . . ?
N1 C9 H16 109.7 . . ?
C10 C9 H16 109.7 . . ?
H15 C9 H16 108.2 . . ?
C9 C10 C11 114.3(4) . . ?
C9 C10 H17 108.7 . . ?
C11 C10 H17 108.7 . . ?
C9 C10 H18 108.7 . . ?
C11 C10 H18 108.7 . . ?
H17 C10 H18 107.6 . . ?
N2 C11 C10 112.2(4) . . ?
N2 C11 H19 109.2 . . ?
C10 C11 H19 109.2 . . ?
N2 C11 H20 109.2 . . ?
C10 C11 H20 109.2 . . ?
H19 C11 H20 107.9 . . ?
C12 N2 C11 112.7(4) . . ?
C12 N2 Mn1 106.5(3) . . ?
C11 N2 Mn1 115.7(3) . . ?
C12 N2 H32 104(4) . . ?
C11 N2 H32 112(4) . . ?
Mn1 N2 H32 104(4) . . ?
N2 C12 C13 109.3(4) . . ?
N2 C12 H21 109.8 . . ?
C13 C12 H21 109.8 . . ?
N2 C12 H22 109.8 . . ?
C13 C12 H22 109.8 . . ?
H21 C12 H22 108.3 . . ?
N3 C13 C12 108.5(4) . . ?
N3 C13 H23 110.0 . . ?
C12 C13 H23 110.0 . . ?
N3 C13 H24 110.0 . . ?
C12 C13 H24 110.0 . . ?
H23 C13 H24 108.4 . . ?
C13 N3 C14 112.1(4) . . ?
C13 N3 Mn1 107.3(3) . . ?
C14 N3 Mn1 116.3(3) . . ?
C13 N3 H31 106(5) . . ?
C14 N3 H31 110(5) . . ?
Mn1 N3 H31 104(5) . . ?
N3 C14 C15 111.7(4) . . ?
N3 C14 H25 109.3 . . ?
C15 C14 H25 109.3 . . ?
N3 C14 H26 109.3 . . ?
C15 C14 H26 109.3 . . ?
H25 C14 H26 107.9 . . ?
C14 C15 C16 116.0(5) . . ?
C14 C15 H27 108.3 . . ?
C16 C15 H27 108.3 . . ?
C14 C15 H28 108.3 . . ?
C16 C15 H28 108.3 . . ?
H27 C15 H28 107.4 . . ?
N4 C16 C15 109.6(4) . . ?
N4 C16 H29 109.7 . . ?
C15 C16 H29 109.7 . . ?
N4 C16 H30 109.7 . . ?
C15 C16 H30 109.7 . . ?
H29 C16 H30 108.2 . . ?
C17 N4 C16 117.1(4) . . ?
C17 N4 Mn1 123.8(3) . . ?
C16 N4 Mn1 118.5(3) . . ?
N4 C17 C18 124.5(5) . . ?
N4 C17 H11 117.8 . . ?
C18 C17 H11 117.8 . . ?
C24 C18 C19 120.0(5) . . ?
C24 C18 C17 121.1(5) . . ?
C19 C18 C17 118.4(5) . . ?
C20 C19 C18 120.5(7) . . ?
C20 C19 H12 119.8 . . ?
C18 C19 H12 119.8 . . ?
C19 C20 O3 125.1(8) . . ?
C19 C20 C22 119.7(6) . . ?
O3 C20 C22 115.2(7) . . ?
C20 O3 C21 116.8(7) . . ?
O3 C21 H4 109.5 . . ?
O3 C21 H5 109.5 . . ?
H4 C21 H5 109.5 . . ?
O3 C21 H6 109.5 . . ?
H4 C21 H6 109.5 . . ?
H5 C21 H6 109.5 . . ?
C20 C22 C23 121.2(6) . . ?
C20 C22 H13 119.4 . . ?
C23 C22 H13 119.4 . . ?
C22 C23 C24 120.5(7) . . ?
C22 C23 H14 119.8 . . ?
C24 C23 H14 119.8 . . ?
O4 C24 C18 124.0(5) . . ?
O4 C24 C23 117.8(5) . . ?
C18 C24 C23 118.2(5) . . ?
C24 O4 Mn1 126.2(3) . . ?
F4 B1 F3 103.5(10) . . ?
F4 B1 F1 115.9(8) . . ?
F3 B1 F1 105.7(7) . . ?
F4 B1 F2 108.5(7) . . ?
F3 B1 F2 99.5(8) . . ?
F1 B1 F2 120.9(8) . . ?
O4 Mn1 O2 179.46(16) . . ?
O4 Mn1 N4 86.94(16) . . ?
O2 Mn1 N4 93.59(16) . . ?
O4 Mn1 N1 93.20(16) . . ?
O2 Mn1 N1 86.65(15) . . ?
N4 Mn1 N1 112.71(16) . . ?
O4 Mn1 N3 93.28(16) . . ?
O2 Mn1 N3 86.71(15) . . ?
N4 Mn1 N3 84.53(16) . . ?
N1 Mn1 N3 161.88(16) . . ?
O4 Mn1 N2 84.67(16) . . ?
O2 Mn1 N2 94.80(16) . . ?
N4 Mn1 N2 161.10(17) . . ?
N1 Mn1 N2 84.69(16) . . ?
N3 Mn1 N2 79.09(16) . . ?

_diffrn_measured_fraction_theta_max 0.902
_diffrn_reflns_theta_full        28.14
_diffrn_measured_fraction_theta_full 0.902
_refine_diff_density_max         1.018
_refine_diff_density_min         -0.809
_refine_diff_density_rms         0.085
####################################################################### 
# 
# 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_163
_database_code_depnum_ccdc_archive 'CCDC 1441059'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H32 F3 Mn N4 O7 S'
_chemical_formula_weight         644.55

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pca2(1)

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

_cell_length_a                   20.502(3)
_cell_length_b                   8.2046(14)
_cell_length_c                   16.843(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2833.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9937
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      28.45

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1336
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20853
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         28.45
_reflns_number_total             6523
_reflns_number_gt                6355
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0343P)²+1.9681P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.111(14)
_refine_ls_number_reflns         6523
_refine_ls_number_parameters     380
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0903
_refine_ls_wR_factor_gt          0.0889
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
C1 C 0.01655(16) 1.6667(3) 0.41481(19) 0.0399(7) Uani 1 1 d . . .
H9 H 0.0068 1.6005 0.3679 0.060 Uiso 1 1 calc R . .
H10 H 0.0639 1.6750 0.4215 0.060 Uiso 1 1 calc R . .
H11 H -0.0019 1.7760 0.4079 0.060 Uiso 1 1 calc R . .
O1 O -0.01110(10) 1.5927(2) 0.48281(13) 0.0342(4) Uani 1 1 d . . .
C2 C 0.01013(11) 1.4388(3) 0.50172(14) 0.0205(4) Uani 1 1 d . . .
C3 C 0.05935(11) 1.3554(3) 0.46172(13) 0.0211(4) Uani 1 1 d . . .
H1 H 0.0791 1.4022 0.4161 0.025 Uiso 1 1 calc R . .
C4 C 0.07933(11) 1.2041(3) 0.48862(13) 0.0213(4) Uani 1 1 d . . .
H2 H 0.1119 1.1466 0.4599 0.026 Uiso 1 1 calc R . .
C5 C 0.05276(10) 1.1336(2) 0.55729(12) 0.0173(4) Uani 1 1 d . . .
C6 C 0.00259(10) 1.2189(2) 0.59658(12) 0.0168(4) Uani 1 1 d . . .
C7 C -0.01931(10) 1.3686(3) 0.56731(13) 0.0194(4) Uani 1 1 d . . .
H3 H -0.0546 1.4226 0.5926 0.023 Uiso 1 1 calc R . .
C8 C -0.02973(10) 1.1516(2) 0.66590(12) 0.0191(4) Uani 1 1 d . . .
H4 H -0.0713 1.1939 0.6799 0.023 Uiso 1 1 calc R . .
N1 N -0.00561(9) 1.0389(2) 0.70912(11) 0.0188(3) Uani 1 1 d . . .
C9 C -0.04766(12) 0.9651(3) 0.77006(14) 0.0234(4) Uani 1 1 d . . .
H15 H -0.0870 1.0332 0.7777 0.028 Uiso 1 1 calc R . .
H16 H -0.0239 0.9598 0.8212 0.028 Uiso 1 1 calc R . .
C10 C -0.06781(12) 0.7935(3) 0.74464(15) 0.0278(5) Uani 1 1 d . . .
H17 H -0.1024 0.7545 0.7810 0.033 Uiso 1 1 calc R . .
H18 H -0.0869 0.7995 0.6907 0.033 Uiso 1 1 calc R . .
C11 C -0.01299(13) 0.6692(3) 0.74385(15) 0.0292(5) Uani 1 1 d . . .
H19 H 0.0088 0.6694 0.7963 0.035 Uiso 1 1 calc R . .
H20 H -0.0318 0.5594 0.7354 0.035 Uiso 1 1 calc R . .
N2 N 0.03616(10) 0.7008(2) 0.68180(13) 0.0246(4) Uani 1 1 d . . .
C12 C 0.08848(13) 0.5768(2) 0.6813(2) 0.0284(5) Uani 1 1 d . . .
H21 H 0.0702 0.4693 0.6665 0.034 Uiso 1 1 calc R . .
H22 H 0.1080 0.5677 0.7348 0.034 Uiso 1 1 calc R . .
C13 C 0.13989(13) 0.6264(3) 0.62217(15) 0.0280(5) Uani 1 1 d . . .
H23 H 0.1739 0.5411 0.6186 0.034 Uiso 1 1 calc R . .
H24 H 0.1201 0.6402 0.5690 0.034 Uiso 1 1 calc R . .
N3 N 0.16905(10) 0.7814(2) 0.64873(11) 0.0219(4) Uani 1 1 d . . .
C14 C 0.21352(13) 0.8507(3) 0.58920(14) 0.0287(5) Uani 1 1 d . . .
H25 H 0.1881 0.8804 0.5414 0.034 Uiso 1 1 calc R . .
H26 H 0.2456 0.7664 0.5735 0.034 Uiso 1 1 calc R . .
C15 C 0.24995(12) 1.0000(3) 0.61817(15) 0.0289(5) Uani 1 1 d . . .
H27 H 0.2829 1.0302 0.5778 0.035 Uiso 1 1 calc R . .
H28 H 0.2736 0.9710 0.6674 0.035 Uiso 1 1 calc R . .
C16 C 0.20717(12) 1.1493(3) 0.63503(14) 0.0233(4) Uani 1 1 d . . .
H29 H 0.2352 1.2439 0.6478 0.028 Uiso 1 1 calc R . .
H30 H 0.1814 1.1764 0.5871 0.028 Uiso 1 1 calc R . .
N4 N 0.16295(9) 1.1170(2) 0.70178(11) 0.0189(3) Uani 1 1 d . . .
C17 C 0.17716(11) 1.1831(3) 0.76810(13) 0.0190(4) Uani 1 1 d . . .
H5 H 0.2101 1.2646 0.7682 0.023 Uiso 1 1 calc R . .
C18 C 0.14678(10) 1.1433(2) 0.84336(13) 0.0173(4) Uani 1 1 d . . .
C19 C 0.11106(10) 0.9978(2) 0.85367(12) 0.0156(4) Uani 1 1 d . . .
O2 O 0.09963(8) 0.89160(17) 0.79578(9) 0.0185(3) Uani 1 1 d . . .
C20 C 0.08950(11) 0.9604(3) 0.93084(13) 0.0183(4) Uani 1 1 d . . .
H6 H 0.0662 0.8620 0.9400 0.022 Uiso 1 1 calc R . .
C21 C 0.10162(12) 1.0643(3) 0.99333(13) 0.0212(4) Uani 1 1 d . . .
H7 H 0.0856 1.0379 1.0446 0.025 Uiso 1 1 calc R . .
C22 C 0.13715(10) 1.2082(3) 0.98253(13) 0.0195(4) Uani 1 1 d . . .
C23 C 0.18103(14) 1.4495(3) 1.03948(16) 0.0290(5) Uani 1 1 d . . .
H12 H 0.1567 1.5199 1.0030 0.043 Uiso 1 1 calc R . .
H13 H 0.2244 1.4277 1.0175 0.043 Uiso 1 1 calc R . .
H14 H 0.1855 1.5039 1.0910 0.043 Uiso 1 1 calc R . .
O3 O 0.14697(9) 1.3000(2) 1.04953(10) 0.0251(3) Uani 1 1 d . . .
C24 C 0.15999(11) 1.2467(2) 0.90792(13) 0.0189(4) Uani 1 1 d . . .
H8 H 0.1847 1.3433 0.9001 0.023 Uiso 1 1 calc R . .
Mn1 Mn 0.088270(14) 0.94102(3) 0.68865(2) 0.01576(8) Uani 1 1 d . . .
C25 C 0.27951(15) 0.7463(4) 0.85413(16) 0.0385(6) Uani 1 1 d . . .
F1 F 0.26483(11) 0.8746(2) 0.80908(13) 0.0507(5) Uani 1 1 d . . .
F2 F 0.22679(14) 0.7129(4) 0.89546(17) 0.0834(9) Uani 1 1 d . . .
F3 F 0.32730(14) 0.7967(4) 0.90119(15) 0.0850(10) Uani 1 1 d . . .
S1 S 0.30448(3) 0.57289(7) 0.79284(4) 0.02472(12) Uani 1 1 d . . .
O7 O 0.36264(12) 0.6294(3) 0.75674(17) 0.0542(7) Uani 1 1 d . . .
O5 O 0.24995(13) 0.5491(2) 0.74123(17) 0.0494(6) Uani 1 1 d . . .
O6 O 0.31322(14) 0.4440(3) 0.84970(18) 0.0537(7) Uani 1 1 d . . .
O4 O 0.07503(8) 0.9885(2) 0.58167(9) 0.0213(3) Uani 1 1 d . . .
H31 H 0.1862(15) 0.755(4) 0.684(2) 0.026(7) Uiso 1 1 d . . .
H32 H 0.0164(15) 0.693(4) 0.637(2) 0.025(7) 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
C1 O1 1.415(3) . ?
C1 H9 0.9800 . ?
C1 H10 0.9800 . ?
C1 H11 0.9800 . ?
O1 C2 1.373(3) . ?
C2 C7 1.384(3) . ?
C2 C3 1.393(3) . ?
C3 C4 1.383(3) . ?
C3 H1 0.9500 . ?
C4 C5 1.404(3) . ?
C4 H2 0.9500 . ?
C5 O4 1.339(3) . ?
C5 C6 1.409(3) . ?
C6 C7 1.398(3) . ?
C6 C8 1.452(3) . ?
C7 H3 0.9500 . ?
C8 N1 1.277(3) . ?
C8 H4 0.9500 . ?
N1 C9 1.471(3) . ?
N1 Mn1 2.1137(19) . ?
C9 C10 1.528(3) . ?
C9 H15 0.9900 . ?
C9 H16 0.9900 . ?
C10 C11 1.518(4) . ?
C10 H17 0.9900 . ?
C10 H18 0.9900 . ?
C11 N2 1.475(3) . ?
C11 H19 0.9900 . ?
C11 H20 0.9900 . ?
N2 C12 1.478(3) . ?
N2 Mn1 2.2449(18) . ?
N2 H32 0.86(3) . ?
C12 C13 1.506(4) . ?
C12 H21 0.9900 . ?
C12 H22 0.9900 . ?
C13 N3 1.475(3) . ?
C13 H23 0.9900 . ?
C13 H24 0.9900 . ?
N3 C14 1.470(3) . ?
N3 Mn1 2.216(2) . ?
N3 H31 0.73(4) . ?
C14 C15 1.515(4) . ?
C14 H25 0.9900 . ?
C14 H26 0.9900 . ?
C15 C16 1.533(3) . ?
C15 H27 0.9900 . ?
C15 H28 0.9900 . ?
C16 N4 1.468(3) . ?
C16 H29 0.9900 . ?
C16 H30 0.9900 . ?
N4 C17 1.276(3) . ?
N4 Mn1 2.1159(18) . ?
C17 C18 1.450(3) . ?
C17 H5 0.9500 . ?
C18 C24 1.406(3) . ?
C18 C19 1.411(3) . ?
C19 O2 1.328(2) . ?
C19 C20 1.407(3) . ?
O2 Mn1 1.8639(16) . ?
C20 C21 1.377(3) . ?
C20 H6 0.9500 . ?
C21 C22 1.399(3) . ?
C21 H7 0.9500 . ?
C22 O3 1.371(2) . ?
C22 C24 1.378(3) . ?
C23 O3 1.422(3) . ?
C23 H12 0.9800 . ?
C23 H13 0.9800 . ?
C23 H14 0.9800 . ?
C24 H8 0.9500 . ?
Mn1 O4 1.8635(17) . ?
C25 F2 1.314(4) . ?
C25 F3 1.326(4) . ?
C25 F1 1.332(4) . ?
C25 S1 1.831(3) . ?
S1 O7 1.416(2) . ?
S1 O5 1.429(2) . ?
S1 O6 1.438(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 C1 H9 109.5 . . ?
O1 C1 H10 109.5 . . ?
H9 C1 H10 109.5 . . ?
O1 C1 H11 109.5 . . ?
H9 C1 H11 109.5 . . ?
H10 C1 H11 109.5 . . ?
C2 O1 C1 117.1(2) . . ?
O1 C2 C7 115.4(2) . . ?
O1 C2 C3 124.7(2) . . ?
C7 C2 C3 119.83(19) . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H1 120.1 . . ?
C2 C3 H1 120.1 . . ?
C3 C4 C5 121.7(2) . . ?
C3 C4 H2 119.2 . . ?
C5 C4 H2 119.2 . . ?
O4 C5 C4 119.14(19) . . ?
O4 C5 C6 123.11(19) . . ?
C4 C5 C6 117.74(19) . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 C8 118.11(19) . . ?
C5 C6 C8 121.47(19) . . ?
C2 C7 C6 120.46(19) . . ?
C2 C7 H3 119.8 . . ?
C6 C7 H3 119.8 . . ?
N1 C8 C6 123.9(2) . . ?
N1 C8 H4 118.1 . . ?
C6 C8 H4 118.1 . . ?
C8 N1 C9 117.97(19) . . ?
C8 N1 Mn1 122.34(15) . . ?
C9 N1 Mn1 119.41(14) . . ?
N1 C9 C10 110.02(19) . . ?
N1 C9 H15 109.7 . . ?
C10 C9 H15 109.7 . . ?
N1 C9 H16 109.7 . . ?
C10 C9 H16 109.7 . . ?
H15 C9 H16 108.2 . . ?
C11 C10 C9 114.9(2) . . ?
C11 C10 H17 108.5 . . ?
C9 C10 H17 108.5 . . ?
C11 C10 H18 108.5 . . ?
C9 C10 H18 108.5 . . ?
H17 C10 H18 107.5 . . ?
N2 C11 C10 113.2(2) . . ?
N2 C11 H19 108.9 . . ?
C10 C11 H19 108.9 . . ?
N2 C11 H20 108.9 . . ?
C10 C11 H20 108.9 . . ?
H19 C11 H20 107.8 . . ?
C11 N2 C12 112.3(2) . . ?
C11 N2 Mn1 116.31(14) . . ?
C12 N2 Mn1 105.01(14) . . ?
C11 N2 H32 107(2) . . ?
C12 N2 H32 107(2) . . ?
Mn1 N2 H32 109(2) . . ?
N2 C12 C13 109.1(2) . . ?
N2 C12 H21 109.9 . . ?
C13 C12 H21 109.9 . . ?
N2 C12 H22 109.9 . . ?
C13 C12 H22 109.9 . . ?
H21 C12 H22 108.3 . . ?
N3 C13 C12 108.4(2) . . ?
N3 C13 H23 110.0 . . ?
C12 C13 H23 110.0 . . ?
N3 C13 H24 110.0 . . ?
C12 C13 H24 110.0 . . ?
H23 C13 H24 108.4 . . ?
C14 N3 C13 112.22(19) . . ?
C14 N3 Mn1 116.23(14) . . ?
C13 N3 Mn1 107.38(15) . . ?
C14 N3 H31 112(3) . . ?
C13 N3 H31 101(2) . . ?
Mn1 N3 H31 107(3) . . ?
N3 C14 C15 113.51(19) . . ?
N3 C14 H25 108.9 . . ?
C15 C14 H25 108.9 . . ?
N3 C14 H26 108.9 . . ?
C15 C14 H26 108.9 . . ?
H25 C14 H26 107.7 . . ?
C14 C15 C16 115.0(2) . . ?
C14 C15 H27 108.5 . . ?
C16 C15 H27 108.5 . . ?
C14 C15 H28 108.5 . . ?
C16 C15 H28 108.5 . . ?
H27 C15 H28 107.5 . . ?
N4 C16 C15 110.54(18) . . ?
N4 C16 H29 109.5 . . ?
C15 C16 H29 109.5 . . ?
N4 C16 H30 109.5 . . ?
C15 C16 H30 109.5 . . ?
H29 C16 H30 108.1 . . ?
C17 N4 C16 116.92(19) . . ?
C17 N4 Mn1 123.16(14) . . ?
C16 N4 Mn1 119.33(14) . . ?
N4 C17 C18 124.86(19) . . ?
N4 C17 H5 117.6 . . ?
C18 C17 H5 117.6 . . ?
C24 C18 C19 121.03(19) . . ?
C24 C18 C17 117.22(18) . . ?
C19 C18 C17 121.43(18) . . ?
O2 C19 C20 118.67(18) . . ?
O2 C19 C18 123.77(18) . . ?
C20 C19 C18 117.47(19) . . ?
C19 O2 Mn1 126.16(13) . . ?
C21 C20 C19 120.95(19) . . ?
C21 C20 H6 119.5 . . ?
C19 C20 H6 119.5 . . ?
C20 C21 C22 121.1(2) . . ?
C20 C21 H7 119.4 . . ?
C22 C21 H7 119.4 . . ?
O3 C22 C24 125.10(19) . . ?
O3 C22 C21 115.64(19) . . ?
C24 C22 C21 119.26(19) . . ?
O3 C23 H12 109.5 . . ?
O3 C23 H13 109.5 . . ?
H12 C23 H13 109.5 . . ?
O3 C23 H14 109.5 . . ?
H12 C23 H14 109.5 . . ?
H13 C23 H14 109.5 . . ?
C22 O3 C23 116.60(18) . . ?
C22 C24 C18 120.13(19) . . ?
C22 C24 H8 119.9 . . ?
C18 C24 H8 119.9 . . ?
O4 Mn1 O2 178.72(7) . . ?
O4 Mn1 N1 86.88(7) . . ?
O2 Mn1 N1 92.21(7) . . ?
O4 Mn1 N4 93.65(7) . . ?
O2 Mn1 N4 87.52(7) . . ?
N1 Mn1 N4 112.50(7) . . ?
O4 Mn1 N3 86.51(7) . . ?
O2 Mn1 N3 94.12(7) . . ?
N1 Mn1 N3 162.66(7) . . ?
N4 Mn1 N3 83.92(7) . . ?
O4 Mn1 N2 93.71(8) . . ?
O2 Mn1 N2 85.31(7) . . ?
N1 Mn1 N2 84.76(7) . . ?
N4 Mn1 N2 161.58(7) . . ?
N3 Mn1 N2 79.70(8) . . ?
F2 C25 F3 110.9(3) . . ?
F2 C25 F1 106.3(2) . . ?
F3 C25 F1 105.1(3) . . ?
F2 C25 S1 111.5(3) . . ?
F3 C25 S1 111.9(2) . . ?
F1 C25 S1 110.85(19) . . ?
O7 S1 O5 116.23(19) . . ?
O7 S1 O6 114.94(17) . . ?
O5 S1 O6 113.72(16) . . ?
O7 S1 C25 102.89(14) . . ?
O5 S1 C25 103.31(14) . . ?
O6 S1 C25 103.34(16) . . ?
C5 O4 Mn1 122.15(14) . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        28.45
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.056
####################################################################### 
# 
# 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_pca21
_database_code_depnum_ccdc_archive 'CCDC 1441060'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H32 F3 Mn N4 O7 S'
_chemical_formula_weight         644.55

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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           orthorhombic
_symmetry_space_group_name_H-M   Pca2(1)

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

_cell_length_a                   21.107(9)
_cell_length_b                   8.400(4)
_cell_length_c                   17.288(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3065(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9843
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.91

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1336
_exptl_absorpt_coefficient_mu    0.564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13411
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_av_sigmaI/netI    0.0658
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4347
_reflns_number_gt                3799
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.2000P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.16(5)
_refine_ls_number_reflns         4347
_refine_ls_number_parameters     372
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0909
_refine_ls_wR_factor_ref         0.2935
_refine_ls_wR_factor_gt          0.2628
_refine_ls_goodness_of_fit_ref   1.331
_refine_ls_restrained_S_all      1.331
_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
C1 C 0.0141(6) 1.1631(13) 0.7582(10) 0.097(5) Uani 1 1 d . . .
H1 H 0.0116 1.0889 0.8018 0.146 Uiso 1 1 calc R . .
H2 H -0.0108 1.2585 0.7698 0.146 Uiso 1 1 calc R . .
H3 H 0.0584 1.1931 0.7495 0.146 Uiso 1 1 calc R . .
O1 O -0.0106(4) 1.0877(9) 0.6898(6) 0.088(3) Uani 1 1 d . . .
C2 C 0.0113(3) 0.9375(8) 0.6699(7) 0.054(2) Uani 1 1 d . . .
C3 C -0.0166(3) 0.8697(8) 0.6046(6) 0.052(2) Uani 1 1 d . . .
H4 H -0.0506 0.9232 0.5797 0.063 Uiso 1 1 calc R . .
C4 C 0.0606(4) 0.8540(10) 0.7100(6) 0.0559(19) Uani 1 1 d . . .
H5 H 0.0796 0.8987 0.7548 0.067 Uiso 1 1 calc R . .
C5 C 0.0801(4) 0.7068(10) 0.6823(6) 0.0557(19) Uani 1 1 d . . .
H6 H 0.1117 0.6500 0.7100 0.067 Uiso 1 1 calc R . .
C6 C 0.0545(3) 0.6374(8) 0.6136(5) 0.0506(18) Uani 1 1 d . . .
O2 O 0.0770(3) 0.4928(7) 0.5905(4) 0.0555(14) Uani 1 1 d . . .
C7 C 0.0053(3) 0.7201(7) 0.5746(5) 0.0450(17) Uani 1 1 d . . .
C8 C -0.0275(3) 0.6529(8) 0.5052(6) 0.056(2) Uani 1 1 d . . .
H7 H -0.0677 0.6949 0.4912 0.067 Uiso 1 1 calc R . .
N1 N -0.0039(3) 0.5418(7) 0.4641(5) 0.0527(18) Uani 1 1 d . . .
C9 C -0.0453(4) 0.4688(11) 0.4014(7) 0.069(3) Uani 1 1 d . . .
H8 H -0.0217 0.4634 0.3520 0.083 Uiso 1 1 calc R . .
H9 H -0.0837 0.5345 0.3934 0.083 Uiso 1 1 calc R . .
C10 C -0.0642(4) 0.2983(11) 0.4282(7) 0.068(2) Uani 1 1 d . . .
H10 H -0.0820 0.3059 0.4811 0.082 Uiso 1 1 calc R . .
H11 H -0.0984 0.2593 0.3939 0.082 Uiso 1 1 calc R . .
C11 C -0.0108(4) 0.1734(11) 0.4290(7) 0.065(2) Uani 1 1 d . . .
H12 H -0.0296 0.0668 0.4378 0.078 Uiso 1 1 calc R . .
H13 H 0.0100 0.1721 0.3777 0.078 Uiso 1 1 calc R . .
N2 N 0.0386(3) 0.2048(7) 0.4907(5) 0.0571(16) Uani 1 1 d . . .
H14 H 0.0186 0.2000 0.5385 0.069 Uiso 1 1 calc R . .
C12 C 0.0893(4) 0.0827(9) 0.4901(8) 0.064(2) Uani 1 1 d . . .
H15 H 0.1070 0.0725 0.4373 0.077 Uiso 1 1 calc R . .
H16 H 0.0716 -0.0217 0.5054 0.077 Uiso 1 1 calc R . .
C13 C 0.1420(5) 0.1319(9) 0.5469(7) 0.072(3) Uani 1 1 d . . .
H17 H 0.1243 0.1438 0.5997 0.086 Uiso 1 1 calc R . .
H18 H 0.1754 0.0491 0.5485 0.086 Uiso 1 1 calc R . .
N3 N 0.1696(3) 0.2869(7) 0.5203(5) 0.0571(18) Uani 1 1 d . . .
H19 H 0.1935 0.2650 0.4763 0.068 Uiso 1 1 calc R . .
C14 C 0.2153(4) 0.3567(11) 0.5804(7) 0.070(2) Uani 1 1 d . . .
H20 H 0.1914 0.3822 0.6281 0.084 Uiso 1 1 calc R . .
H21 H 0.2475 0.2754 0.5938 0.084 Uiso 1 1 calc R . .
C15 C 0.2485(5) 0.5047(13) 0.5525(8) 0.079(3) Uani 1 1 d . . .
H22 H 0.2716 0.4778 0.5044 0.094 Uiso 1 1 calc R . .
H23 H 0.2805 0.5350 0.5917 0.094 Uiso 1 1 calc R . .
C16 C 0.2062(4) 0.6539(10) 0.5358(6) 0.060(2) Uani 1 1 d . . .
H24 H 0.1802 0.6790 0.5818 0.072 Uiso 1 1 calc R . .
H25 H 0.2334 0.7470 0.5244 0.072 Uiso 1 1 calc R . .
N4 N 0.1636(3) 0.6205(6) 0.4676(4) 0.0483(15) Uani 1 1 d . . .
C17 C 0.1771(3) 0.6858(8) 0.4026(6) 0.0524(19) Uani 1 1 d . . .
H26 H 0.2087 0.7662 0.4025 0.063 Uiso 1 1 calc R . .
C18 C 0.1467(3) 0.6451(8) 0.3263(5) 0.0466(16) Uani 1 1 d . . .
C19 C 0.1587(3) 0.7451(9) 0.2643(6) 0.0512(18) Uani 1 1 d . . .
H27 H 0.1821 0.8405 0.2721 0.061 Uiso 1 1 calc R . .
C20 C 0.1366(3) 0.7060(9) 0.1894(6) 0.0547(19) Uani 1 1 d . . .
O3 O 0.1465(3) 0.7975(7) 0.1232(4) 0.0691(16) Uani 1 1 d . . .
C21 C 0.1795(6) 0.9440(11) 0.1287(8) 0.075(3) Uani 1 1 d . . .
H28 H 0.1680 0.9975 0.1771 0.112 Uiso 1 1 calc R . .
H29 H 0.1682 1.0119 0.0848 0.112 Uiso 1 1 calc R . .
H30 H 0.2253 0.9238 0.1281 0.112 Uiso 1 1 calc R . .
C22 C 0.1012(4) 0.5642(10) 0.1794(7) 0.057(2) Uani 1 1 d . . .
H31 H 0.0850 0.5375 0.1298 0.068 Uiso 1 1 calc R . .
C23 C 0.0900(3) 0.4617(9) 0.2433(7) 0.054(2) Uani 1 1 d . . .
H32 H 0.0672 0.3657 0.2351 0.065 Uiso 1 1 calc R . .
C24 C 0.1119(3) 0.4980(8) 0.3195(4) 0.0409(14) Uani 1 1 d . . .
O4 O 0.1001(2) 0.3937(6) 0.3751(3) 0.0461(12) Uani 1 1 d . . .
Mn1 Mn 0.08944(4) 0.44466(10) 0.48285(9) 0.0438(4) Uani 1 1 d . . .
S1 S 0.30684(10) 0.0779(3) 0.38227(18) 0.0678(7) Uani 1 1 d . . .
O5 O 0.3637(7) 0.1325(17) 0.4129(11) 0.175(8) Uani 1 1 d . . .
O6 O 0.2520(5) 0.0530(10) 0.4313(10) 0.123(5) Uani 1 1 d . . .
O7 O 0.3129(6) -0.0652(15) 0.3268(10) 0.131(5) Uani 1 1 d . . .
F1 F 0.2678(6) 0.3717(12) 0.3590(10) 0.152(5) Uani 1 1 d . . .
F2 F 0.2260(6) 0.202(2) 0.2895(13) 0.211(9) Uani 1 1 d . . .
F3 F 0.3312(6) 0.293(2) 0.2729(10) 0.208(9) Uani 1 1 d . . .
C25 C 0.2830(5) 0.2395(17) 0.3161(7) 0.084(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
C1 O1 1.438(15) . ?
C1 H1 0.9800 . ?
C1 H2 0.9800 . ?
C1 H3 0.9800 . ?
O1 C2 1.387(9) . ?
C2 C3 1.395(13) . ?
C2 C4 1.434(12) . ?
C3 C7 1.436(10) . ?
C3 H4 0.9500 . ?
C4 C5 1.389(13) . ?
C4 H5 0.9500 . ?
C5 C6 1.430(14) . ?
C5 H6 0.9500 . ?
C6 O2 1.364(10) . ?
C6 C7 1.419(11) . ?
O2 Mn1 1.922(7) . ?
C7 C8 1.495(12) . ?
C8 N1 1.274(11) . ?
C8 H7 0.9500 . ?
N1 C9 1.522(12) . ?
N1 Mn1 2.157(6) . ?
C9 C10 1.557(13) . ?
C9 H8 0.9900 . ?
C9 H9 0.9900 . ?
C10 C11 1.540(15) . ?
C10 H10 0.9900 . ?
C10 H11 0.9900 . ?
C11 N2 1.515(13) . ?
C11 H12 0.9900 . ?
C11 H13 0.9900 . ?
N2 C12 1.482(11) . ?
N2 Mn1 2.286(6) . ?
N2 H14 0.9300 . ?
C12 C13 1.541(17) . ?
C12 H15 0.9900 . ?
C12 H16 0.9900 . ?
C13 N3 1.499(10) . ?
C13 H17 0.9900 . ?
C13 H18 0.9900 . ?
N3 C14 1.534(13) . ?
N3 Mn1 2.245(6) . ?
N3 H19 0.9300 . ?
C14 C15 1.506(17) . ?
C14 H20 0.9900 . ?
C14 H21 0.9900 . ?
C15 C16 1.565(14) . ?
C15 H22 0.9900 . ?
C15 H23 0.9900 . ?
C16 N4 1.509(10) . ?
C16 H24 0.9900 . ?
C16 H25 0.9900 . ?
N4 C17 1.282(12) . ?
N4 Mn1 2.169(5) . ?
C17 C18 1.506(12) . ?
C17 H26 0.9500 . ?
C18 C19 1.386(12) . ?
C18 C24 1.442(9) . ?
C19 C20 1.416(14) . ?
C19 H27 0.9500 . ?
C20 O3 1.394(11) . ?
C20 C22 1.416(11) . ?
O3 C21 1.418(11) . ?
C21 H28 0.9800 . ?
C21 H29 0.9800 . ?
C21 H30 0.9800 . ?
C22 C23 1.422(15) . ?
C22 H31 0.9500 . ?
C23 C24 1.428(14) . ?
C23 H32 0.9500 . ?
C24 O4 1.325(9) . ?
O4 Mn1 1.924(6) . ?
S1 O5 1.390(10) . ?
S1 O6 1.449(10) . ?
S1 O7 1.542(13) . ?
S1 C25 1.846(12) . ?
F1 C25 1.374(18) . ?
F2 C25 1.326(17) . ?
F3 C25 1.339(17) . ?

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 C1 H1 109.5 . . ?
O1 C1 H2 109.5 . . ?
H1 C1 H2 109.5 . . ?
O1 C1 H3 109.5 . . ?
H1 C1 H3 109.5 . . ?
H2 C1 H3 109.5 . . ?
C2 O1 C1 118.9(8) . . ?
O1 C2 C3 115.5(7) . . ?
O1 C2 C4 124.5(9) . . ?
C3 C2 C4 119.9(7) . . ?
C2 C3 C7 120.9(7) . . ?
C2 C3 H4 119.5 . . ?
C7 C3 H4 119.5 . . ?
C5 C4 C2 119.0(9) . . ?
C5 C4 H5 120.5 . . ?
C2 C4 H5 120.5 . . ?
C4 C5 C6 122.5(8) . . ?
C4 C5 H6 118.8 . . ?
C6 C5 H6 118.8 . . ?
O2 C6 C7 123.5(8) . . ?
O2 C6 C5 118.3(7) . . ?
C7 C6 C5 118.2(7) . . ?
C6 O2 Mn1 121.2(6) . . ?
C6 C7 C3 119.5(8) . . ?
C6 C7 C8 122.3(6) . . ?
C3 C7 C8 118.1(7) . . ?
N1 C8 C7 122.8(6) . . ?
N1 C8 H7 118.6 . . ?
C7 C8 H7 118.6 . . ?
C8 N1 C9 117.9(7) . . ?
C8 N1 Mn1 123.4(6) . . ?
C9 N1 Mn1 118.6(5) . . ?
N1 C9 C10 107.8(9) . . ?
N1 C9 H8 110.1 . . ?
C10 C9 H8 110.1 . . ?
N1 C9 H9 110.1 . . ?
C10 C9 H9 110.1 . . ?
H8 C9 H9 108.5 . . ?
C11 C10 C9 116.2(7) . . ?
C11 C10 H10 108.2 . . ?
C9 C10 H10 108.2 . . ?
C11 C10 H11 108.2 . . ?
C9 C10 H11 108.2 . . ?
H10 C10 H11 107.4 . . ?
N2 C11 C10 113.0(8) . . ?
N2 C11 H12 109.0 . . ?
C10 C11 H12 109.0 . . ?
N2 C11 H13 109.0 . . ?
C10 C11 H13 109.0 . . ?
H12 C11 H13 107.8 . . ?
C12 N2 C11 111.8(8) . . ?
C12 N2 Mn1 105.7(4) . . ?
C11 N2 Mn1 115.8(5) . . ?
C12 N2 H14 107.7 . . ?
C11 N2 H14 107.7 . . ?
Mn1 N2 H14 107.7 . . ?
N2 C12 C13 109.3(8) . . ?
N2 C12 H15 109.8 . . ?
C13 C12 H15 109.8 . . ?
N2 C12 H16 109.8 . . ?
C13 C12 H16 109.8 . . ?
H15 C12 H16 108.3 . . ?
N3 C13 C12 108.5(8) . . ?
N3 C13 H17 110.0 . . ?
C12 C13 H17 110.0 . . ?
N3 C13 H18 110.0 . . ?
C12 C13 H18 110.0 . . ?
H17 C13 H18 108.4 . . ?
C13 N3 C14 111.6(8) . . ?
C13 N3 Mn1 107.9(5) . . ?
C14 N3 Mn1 116.3(5) . . ?
C13 N3 H19 106.8 . . ?
C14 N3 H19 106.8 . . ?
Mn1 N3 H19 106.8 . . ?
C15 C14 N3 113.0(9) . . ?
C15 C14 H20 109.0 . . ?
N3 C14 H20 109.0 . . ?
C15 C14 H21 109.0 . . ?
N3 C14 H21 109.0 . . ?
H20 C14 H21 107.8 . . ?
C14 C15 C16 117.1(8) . . ?
C14 C15 H22 108.0 . . ?
C16 C15 H22 108.0 . . ?
C14 C15 H23 108.0 . . ?
C16 C15 H23 108.0 . . ?
H22 C15 H23 107.3 . . ?
N4 C16 C15 109.6(7) . . ?
N4 C16 H24 109.8 . . ?
C15 C16 H24 109.8 . . ?
N4 C16 H25 109.8 . . ?
C15 C16 H25 109.8 . . ?
H24 C16 H25 108.2 . . ?
C17 N4 C16 118.3(6) . . ?
C17 N4 Mn1 123.9(5) . . ?
C16 N4 Mn1 117.5(5) . . ?
N4 C17 C18 125.2(6) . . ?
N4 C17 H26 117.4 . . ?
C18 C17 H26 117.4 . . ?
C19 C18 C24 123.3(8) . . ?
C19 C18 C17 117.5(6) . . ?
C24 C18 C17 118.9(7) . . ?
C18 C19 C20 120.4(6) . . ?
C18 C19 H27 119.8 . . ?
C20 C19 H27 119.8 . . ?
O3 C20 C22 116.3(9) . . ?
O3 C20 C19 124.9(7) . . ?
C22 C20 C19 118.7(8) . . ?
C20 O3 C21 119.9(8) . . ?
O3 C21 H28 109.5 . . ?
O3 C21 H29 109.5 . . ?
H28 C21 H29 109.5 . . ?
O3 C21 H30 109.5 . . ?
H28 C21 H30 109.5 . . ?
H29 C21 H30 109.5 . . ?
C20 C22 C23 120.2(9) . . ?
C20 C22 H31 119.9 . . ?
C23 C22 H31 119.9 . . ?
C22 C23 C24 122.3(7) . . ?
C22 C23 H32 118.9 . . ?
C24 C23 H32 118.9 . . ?
O4 C24 C23 117.9(6) . . ?
O4 C24 C18 127.1(7) . . ?
C23 C24 C18 115.0(7) . . ?
C24 O4 Mn1 125.3(5) . . ?
O2 Mn1 O4 178.7(2) . . ?
O2 Mn1 N1 86.6(3) . . ?
O4 Mn1 N1 92.6(3) . . ?
O2 Mn1 N4 94.2(3) . . ?
O4 Mn1 N4 87.1(2) . . ?
N1 Mn1 N4 112.5(2) . . ?
O2 Mn1 N3 87.0(3) . . ?
O4 Mn1 N3 93.4(3) . . ?
N1 Mn1 N3 162.8(3) . . ?
N4 Mn1 N3 83.8(2) . . ?
O2 Mn1 N2 93.7(3) . . ?
O4 Mn1 N2 85.2(3) . . ?
N1 Mn1 N2 85.1(2) . . ?
N4 Mn1 N2 161.1(2) . . ?
N3 Mn1 N2 79.4(3) . . ?
O5 S1 O6 121.0(12) . . ?
O5 S1 O7 115.0(10) . . ?
O6 S1 O7 108.5(8) . . ?
O5 S1 C25 103.2(7) . . ?
O6 S1 C25 104.5(6) . . ?
O7 S1 C25 102.1(8) . . ?
F2 C25 F3 125.1(17) . . ?
F2 C25 F1 99.6(12) . . ?
F3 C25 F1 102.0(15) . . ?
F2 C25 S1 106.7(12) . . ?
F3 C25 S1 112.6(8) . . ?
F1 C25 S1 108.9(10) . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.783
_refine_diff_density_min         -1.336
_refine_diff_density_rms         0.249
####################################################################### 
# 
# 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_m1
_database_code_depnum_ccdc_archive 'CCDC 1441061'
_audit_update_record             
;
2016-02-05 deposited with the CCDC.
2016-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H32 Cl Mn N4 O8'
_chemical_formula_weight         594.93

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   P2/c

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

_cell_length_a                   17.778(4)
_cell_length_b                   8.5035(17)
_cell_length_c                   17.534(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.61(3)
_cell_angle_gamma                90.00
_cell_volume                     2633.1(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9375
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      28.24

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1240
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17316
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_av_sigmaI/netI    0.0753
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4628
_reflns_number_gt                3526
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0406P)²+22.3868P] 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         4628
_refine_ls_number_parameters     358
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0985
_refine_ls_wR_factor_ref         0.2181
_refine_ls_wR_factor_gt          0.2071
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_restrained_S_all      1.126
_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
C1 C 0.7725(6) 0.7943(11) 0.8844(5) 0.060(3) Uani 1 1 d . . .
H1 H 0.8141 0.8393 0.8616 0.090 Uiso 1 1 calc R . .
H2 H 0.7513 0.8721 0.9154 0.090 Uiso 1 1 calc R . .
H3 H 0.7345 0.7595 0.8447 0.090 Uiso 1 1 calc R . .
O1 O 0.7988(3) 0.6632(6) 0.9315(3) 0.0364(12) Uani 1 1 d . . .
C2 C 0.8263(4) 0.5355(8) 0.8952(4) 0.0300(16) Uani 1 1 d . . .
C3 C 0.8334(4) 0.3980(8) 0.9382(4) 0.0297(16) Uani 1 1 d . . .
H7 H 0.8184 0.3973 0.9872 0.036 Uiso 1 1 calc R . .
C4 C 0.8622(4) 0.2627(9) 0.9096(4) 0.0295(16) Uani 1 1 d . . .
C5 C 0.8891(4) 0.2618(8) 0.8366(4) 0.0265(15) Uani 1 1 d . . .
O2 O 0.9216(2) 0.1332(5) 0.8129(3) 0.0264(10) Uani 1 1 d . . .
Mn1 Mn 1.0000 0.14035(17) 0.7500 0.0257(4) Uani 1 2 d S . .
C6 C 0.8473(4) 0.5376(8) 0.8213(4) 0.0293(16) Uani 1 1 d . . .
H8 H 0.8400 0.6275 0.7912 0.035 Uiso 1 1 calc R . .
C7 C 0.8798(4) 0.4021(8) 0.7923(4) 0.0284(15) Uani 1 1 d . . .
C8 C 0.8949(4) 0.3967(8) 0.7133(4) 0.0273(15) Uani 1 1 d . . .
H9 H 0.8706 0.4702 0.6798 0.033 Uiso 1 1 calc R . .
N1 N 0.9394(3) 0.2978(6) 0.6855(3) 0.0258(12) Uani 1 1 d . . .
C9 C 0.9338(4) 0.2868(8) 0.6002(4) 0.0284(15) Uani 1 1 d . . .
H14 H 0.9839 0.2963 0.5837 0.034 Uiso 1 1 calc R . .
H15 H 0.9029 0.3725 0.5774 0.034 Uiso 1 1 calc R . .
C10 C 0.8988(4) 0.1305(8) 0.5728(4) 0.0308(16) Uani 1 1 d . . .
H16 H 0.8910 0.1315 0.5171 0.037 Uiso 1 1 calc R . .
H17 H 0.8493 0.1221 0.5908 0.037 Uiso 1 1 calc R . .
C11 C 0.9444(4) -0.0159(9) 0.5985(4) 0.0326(16) Uani 1 1 d . . .
H18 H 0.9202 -0.1077 0.5736 0.039 Uiso 1 1 calc R . .
H19 H 0.9947 -0.0073 0.5827 0.039 Uiso 1 1 calc R . .
N2 N 0.9505(3) -0.0370(7) 0.6829(3) 0.0264(13) Uani 1 1 d D . .
C12 C 0.9918(4) -0.1851(8) 0.7065(4) 0.0323(16) Uani 1 1 d . . .
H20 H 1.0388 -0.1904 0.6835 0.039 Uiso 1 1 calc R . .
H21 H 0.9612 -0.2757 0.6896 0.039 Uiso 1 1 calc R . .
C13 C 0.4189(11) 0.9044(19) 0.4887(7) 0.129(7) Uani 1 1 d . . .
H4 H 0.4324 0.9305 0.5418 0.194 Uiso 1 1 calc R . .
H5 H 0.3893 0.9881 0.4637 0.194 Uiso 1 1 calc R . .
H6 H 0.4641 0.8899 0.4643 0.194 Uiso 1 1 calc R . .
O3 O 0.3809(7) 0.7799(11) 0.4839(5) 0.112(4) Uani 1 1 d . . .
C14 C 0.4082(6) 0.6504(13) 0.5269(5) 0.063(3) Uani 1 1 d . . .
C15 C 0.3601(5) 0.5227(14) 0.5201(5) 0.061(3) Uani 1 1 d . . .
H10 H 0.3150 0.5294 0.4876 0.073 Uiso 1 1 calc R . .
C16 C 0.3766(4) 0.3879(12) 0.5593(4) 0.048(2) Uani 1 1 d . . .
H11 H 0.3427 0.3043 0.5530 0.057 Uiso 1 1 calc R . .
C17 C 0.4435(4) 0.3710(9) 0.6094(4) 0.0339(17) Uani 1 1 d . . .
O4 O 0.4568(3) 0.2341(6) 0.6480(3) 0.0358(12) Uani 1 1 d . . .
C18 C 0.4763(6) 0.6352(9) 0.5727(5) 0.052(2) Uani 1 1 d . . .
H12 H 0.5107 0.7181 0.5759 0.062 Uiso 1 1 calc R . .
C19 C 0.4948(4) 0.4957(9) 0.6149(4) 0.0359(18) Uani 1 1 d . . .
C20 C 0.5678(4) 0.4815(9) 0.6573(4) 0.0376(18) Uani 1 1 d . . .
H13 H 0.6058 0.5488 0.6447 0.045 Uiso 1 1 calc R . .
N4 N 0.5847(3) 0.3808(8) 0.7121(4) 0.0346(15) Uani 1 1 d . . .
C21 C 0.6652(4) 0.3621(11) 0.7429(5) 0.047(2) Uani 1 1 d . . .
H22 H 0.6710 0.3795 0.7979 0.057 Uiso 1 1 calc R . .
H23 H 0.6954 0.4401 0.7198 0.057 Uiso 1 1 calc R . .
C22 C 0.6935(4) 0.1983(11) 0.7259(5) 0.048(2) Uani 1 1 d . . .
H24 H 0.6854 0.1817 0.6709 0.058 Uiso 1 1 calc R . .
H25 H 0.7477 0.1950 0.7412 0.058 Uiso 1 1 calc R . .
C23 C 0.6576(4) 0.0640(11) 0.7644(5) 0.049(2) Uani 1 1 d . . .
H26 H 0.6869 -0.0307 0.7588 0.059 Uiso 1 1 calc R . .
H27 H 0.6593 0.0863 0.8188 0.059 Uiso 1 1 calc R . .
N3 N 0.5770(4) 0.0353(8) 0.7317(4) 0.0368(15) Uani 1 1 d . . .
C24 C 0.5426(5) -0.1063(10) 0.7629(5) 0.051(2) Uani 1 1 d . . .
H28 H 0.5517 -0.1059 0.8185 0.061 Uiso 1 1 calc R . .
H29 H 0.5655 -0.2003 0.7443 0.061 Uiso 1 1 calc R . .
Mn2 Mn 0.5000 0.23536(19) 0.7500 0.0313(4) Uani 1 2 d S . .
Cl1 Cl 0.74817(9) 0.7882(2) 0.62411(10) 0.0323(4) Uani 1 1 d . . .
O5 O 0.6689(2) 0.8054(6) 0.6345(3) 0.0329(12) Uani 1 1 d . . .
O6 O 0.7634(3) 0.8681(6) 0.5552(3) 0.0395(13) Uani 1 1 d . . .
O7 O 0.7938(3) 0.8558(8) 0.6902(3) 0.0499(16) Uani 1 1 d . . .
O8 O 0.7662(3) 0.6220(7) 0.6188(3) 0.0515(16) Uani 1 1 d . . .
H31 H 0.903(3) -0.047(10) 0.696(4) 0.05(2) Uiso 1 1 d D . .
H32 H 0.868(4) 0.172(9) 0.941(4) 0.04(2) Uiso 1 1 d . . .
H30 H 0.582(4) 0.031(9) 0.682(4) 0.03(2) 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
C1 O1 1.433(9) . ?
C1 H1 0.9600 . ?
C1 H2 0.9600 . ?
C1 H3 0.9600 . ?
O1 C2 1.377(8) . ?
C2 C6 1.390(10) . ?
C2 C3 1.389(10) . ?
C3 C4 1.377(10) . ?
C3 H7 0.9300 . ?
C4 C5 1.417(9) . ?
C4 H32 0.94(8) . ?
C5 O2 1.326(8) . ?
C5 C7 1.422(10) . ?
O2 Mn1 1.875(4) . ?
Mn1 O2 1.875(4) 2_756 ?
Mn1 N1 1.988(6) 2_756 ?
Mn1 N1 1.988(6) . ?
Mn1 N2 2.049(6) . ?
Mn1 N2 2.049(6) 2_756 ?
C6 C7 1.409(9) . ?
C6 H8 0.9300 . ?
C7 C8 1.443(9) . ?
C8 N1 1.288(8) . ?
C8 H9 0.9300 . ?
N1 C9 1.491(8) . ?
C9 C10 1.522(9) . ?
C9 H14 0.9700 . ?
C9 H15 0.9700 . ?
C10 C11 1.525(10) . ?
C10 H16 0.9700 . ?
C10 H17 0.9700 . ?
C11 N2 1.481(9) . ?
C11 H18 0.9700 . ?
C11 H19 0.9700 . ?
N2 C12 1.492(9) . ?
N2 H31 0.90(4) . ?
C12 C12 1.519(13) 2_756 ?
C12 H20 0.9700 . ?
C12 H21 0.9700 . ?
C13 O3 1.253(19) . ?
C13 H4 0.9600 . ?
C13 H5 0.9600 . ?
C13 H6 0.9600 . ?
O3 C14 1.390(12) . ?
C14 C15 1.379(15) . ?
C14 C18 1.381(14) . ?
C15 C16 1.352(13) . ?
C15 H10 0.9300 . ?
C16 C17 1.401(10) . ?
C16 H11 0.9300 . ?
C17 O4 1.353(9) . ?
C17 C19 1.395(10) . ?
O4 Mn2 1.864(5) . ?
C18 C19 1.417(11) . ?
C18 H12 0.9300 . ?
C19 C20 1.425(11) . ?
C20 N4 1.298(10) . ?
C20 H13 0.9300 . ?
N4 C21 1.478(9) . ?
N4 Mn2 2.114(6) . ?
C21 C22 1.521(12) . ?
C21 H22 0.9700 . ?
C21 H23 0.9700 . ?
C22 C23 1.504(12) . ?
C22 H24 0.9700 . ?
C22 H25 0.9700 . ?
C23 N3 1.502(10) . ?
C23 H26 0.9700 . ?
C23 H27 0.9700 . ?
N3 C24 1.483(10) . ?
N3 Mn2 2.229(6) . ?
N3 H30 0.89(7) . ?
C24 C24 1.531(18) 2_656 ?
C24 H28 0.9700 . ?
C24 H29 0.9700 . ?
Mn2 O4 1.864(5) 2_656 ?
Mn2 N4 2.114(6) 2_656 ?
Mn2 N3 2.229(6) 2_656 ?
Cl1 O6 1.438(5) . ?
Cl1 O5 1.448(4) . ?
Cl1 O8 1.454(6) . ?
Cl1 O7 1.454(5) . ?

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 C1 H1 109.5 . . ?
O1 C1 H2 109.5 . . ?
H1 C1 H2 109.5 . . ?
O1 C1 H3 109.5 . . ?
H1 C1 H3 109.5 . . ?
H2 C1 H3 109.5 . . ?
C2 O1 C1 117.2(6) . . ?
O1 C2 C6 124.7(7) . . ?
O1 C2 C3 115.4(6) . . ?
C6 C2 C3 119.9(7) . . ?
C4 C3 C2 121.4(7) . . ?
C4 C3 H7 119.3 . . ?
C2 C3 H7 119.3 . . ?
C3 C4 C5 120.7(7) . . ?
C3 C4 H32 120(5) . . ?
C5 C4 H32 120(5) . . ?
O2 C5 C4 119.5(6) . . ?
O2 C5 C7 123.3(6) . . ?
C4 C5 C7 117.3(6) . . ?
C5 O2 Mn1 122.5(4) . . ?
O2 Mn1 O2 176.3(3) . 2_756 ?
O2 Mn1 N1 94.5(2) . 2_756 ?
O2 Mn1 N1 88.0(2) 2_756 2_756 ?
O2 Mn1 N1 88.0(2) . . ?
O2 Mn1 N1 94.5(2) 2_756 . ?
N1 Mn1 N1 95.3(3) 2_756 . ?
O2 Mn1 N2 90.8(2) . . ?
O2 Mn1 N2 86.4(2) 2_756 . ?
N1 Mn1 N2 172.6(2) 2_756 . ?
N1 Mn1 N2 90.0(2) . . ?
O2 Mn1 N2 86.4(2) . 2_756 ?
O2 Mn1 N2 90.8(2) 2_756 2_756 ?
N1 Mn1 N2 90.0(2) 2_756 2_756 ?
N1 Mn1 N2 172.6(2) . 2_756 ?
N2 Mn1 N2 85.2(3) . 2_756 ?
C2 C6 C7 119.4(7) . . ?
C2 C6 H8 120.3 . . ?
C7 C6 H8 120.3 . . ?
C6 C7 C5 121.1(6) . . ?
C6 C7 C8 120.1(6) . . ?
C5 C7 C8 118.3(6) . . ?
N1 C8 C7 125.1(6) . . ?
N1 C8 H9 117.5 . . ?
C7 C8 H9 117.5 . . ?
C8 N1 C9 116.6(6) . . ?
C8 N1 Mn1 122.7(5) . . ?
C9 N1 Mn1 119.9(4) . . ?
N1 C9 C10 110.4(5) . . ?
N1 C9 H14 109.6 . . ?
C10 C9 H14 109.6 . . ?
N1 C9 H15 109.6 . . ?
C10 C9 H15 109.6 . . ?
H14 C9 H15 108.1 . . ?
C9 C10 C11 115.8(6) . . ?
C9 C10 H16 108.3 . . ?
C11 C10 H16 108.3 . . ?
C9 C10 H17 108.3 . . ?
C11 C10 H17 108.3 . . ?
H16 C10 H17 107.4 . . ?
N2 C11 C10 111.7(6) . . ?
N2 C11 H18 109.3 . . ?
C10 C11 H18 109.3 . . ?
N2 C11 H19 109.3 . . ?
C10 C11 H19 109.3 . . ?
H18 C11 H19 107.9 . . ?
C11 N2 C12 110.9(5) . . ?
C11 N2 Mn1 117.5(4) . . ?
C12 N2 Mn1 107.2(4) . . ?
C11 N2 H31 108(5) . . ?
C12 N2 H31 107(5) . . ?
Mn1 N2 H31 106(5) . . ?
N2 C12 C12 108.1(4) . 2_756 ?
N2 C12 H20 110.1 . . ?
C12 C12 H20 110.1 2_756 . ?
N2 C12 H21 110.1 . . ?
C12 C12 H21 110.1 2_756 . ?
H20 C12 H21 108.4 . . ?
O3 C13 H4 109.5 . . ?
O3 C13 H5 109.5 . . ?
H4 C13 H5 109.5 . . ?
O3 C13 H6 109.5 . . ?
H4 C13 H6 109.5 . . ?
H5 C13 H6 109.5 . . ?
C13 O3 C14 118.8(14) . . ?
C15 C14 C18 118.0(9) . . ?
C15 C14 O3 113.8(10) . . ?
C18 C14 O3 128.1(12) . . ?
C16 C15 C14 121.9(9) . . ?
C16 C15 H10 119.1 . . ?
C14 C15 H10 119.1 . . ?
C15 C16 C17 121.6(9) . . ?
C15 C16 H11 119.2 . . ?
C17 C16 H11 119.2 . . ?
O4 C17 C19 122.9(7) . . ?
O4 C17 C16 119.2(7) . . ?
C19 C17 C16 117.8(8) . . ?
C17 O4 Mn2 120.3(4) . . ?
C14 C18 C19 121.1(9) . . ?
C14 C18 H12 119.4 . . ?
C19 C18 H12 119.4 . . ?
C17 C19 C18 119.3(8) . . ?
C17 C19 C20 121.5(7) . . ?
C18 C19 C20 119.0(8) . . ?
N4 C20 C19 124.1(7) . . ?
N4 C20 H13 117.9 . . ?
C19 C20 H13 117.9 . . ?
C20 N4 C21 118.2(7) . . ?
C20 N4 Mn2 120.4(5) . . ?
C21 N4 Mn2 121.2(5) . . ?
N4 C21 C22 110.8(6) . . ?
N4 C21 H22 109.5 . . ?
C22 C21 H22 109.5 . . ?
N4 C21 H23 109.5 . . ?
C22 C21 H23 109.5 . . ?
H22 C21 H23 108.1 . . ?
C23 C22 C21 116.2(7) . . ?
C23 C22 H24 108.2 . . ?
C21 C22 H24 108.2 . . ?
C23 C22 H25 108.2 . . ?
C21 C22 H25 108.2 . . ?
H24 C22 H25 107.4 . . ?
N3 C23 C22 112.8(7) . . ?
N3 C23 H26 109.0 . . ?
C22 C23 H26 109.0 . . ?
N3 C23 H27 109.0 . . ?
C22 C23 H27 109.0 . . ?
H26 C23 H27 107.8 . . ?
C24 N3 C23 114.0(7) . . ?
C24 N3 Mn2 106.4(5) . . ?
C23 N3 Mn2 113.4(5) . . ?
C24 N3 H30 115(5) . . ?
C23 N3 H30 101(5) . . ?
Mn2 N3 H30 107(5) . . ?
N3 C24 C24 109.1(6) . 2_656 ?
N3 C24 H28 109.9 . . ?
C24 C24 H28 109.9 2_656 . ?
N3 C24 H29 109.9 . . ?
C24 C24 H29 109.9 2_656 . ?
H28 C24 H29 108.3 . . ?
O4 Mn2 O4 179.3(3) 2_656 . ?
O4 Mn2 N4 94.3(2) 2_656 . ?
O4 Mn2 N4 86.1(2) . . ?
O4 Mn2 N4 86.1(2) 2_656 2_656 ?
O4 Mn2 N4 94.3(2) . 2_656 ?
N4 Mn2 N4 108.4(3) . 2_656 ?
O4 Mn2 N3 92.9(2) 2_656 2_656 ?
O4 Mn2 N3 86.6(2) . 2_656 ?
N4 Mn2 N3 164.3(2) . 2_656 ?
N4 Mn2 N3 86.0(2) 2_656 2_656 ?
O4 Mn2 N3 86.6(2) 2_656 . ?
O4 Mn2 N3 92.9(2) . . ?
N4 Mn2 N3 86.0(2) . . ?
N4 Mn2 N3 164.3(2) 2_656 . ?
N3 Mn2 N3 80.5(3) 2_656 . ?
O6 Cl1 O5 109.7(3) . . ?
O6 Cl1 O8 110.0(3) . . ?
O5 Cl1 O8 109.3(3) . . ?
O6 Cl1 O7 109.9(3) . . ?
O5 Cl1 O7 108.8(3) . . ?
O8 Cl1 O7 109.2(4) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.733
_refine_diff_density_min         -0.852
_refine_diff_density_rms         0.111
####################################################################### 
# 
# 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_m2
_database_code_depnum_ccdc_archive 'CCDC 1441062'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H32 Cl Mn N4 O8'
_chemical_formula_weight         594.93

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   P2/c

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

_cell_length_a                   17.925(4)
_cell_length_b                   8.5661(17)
_cell_length_c                   17.723(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.05(3)
_cell_angle_gamma                90.00
_cell_volume                     2706.2(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9322
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      28.22

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1240
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.891
_exptl_absorpt_correction_T_max  0.932
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21576
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         27.48
_reflns_number_total             6190
_reflns_number_gt                3957
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1354P)²+0.0000P] 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         6190
_refine_ls_number_parameters     354
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1151
_refine_ls_R_factor_gt           0.0798
_refine_ls_wR_factor_ref         0.2544
_refine_ls_wR_factor_gt          0.2196
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_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
C1 C 0.7732(5) 1.3026(8) 0.3769(4) 0.118(2) Uani 1 1 d . . .
H1 H 0.8147 1.3450 0.3535 0.176 Uiso 1 1 calc R . .
H2 H 0.7530 1.3814 0.4075 0.176 Uiso 1 1 calc R . .
H3 H 0.7351 1.2685 0.3383 0.176 Uiso 1 1 calc R . .
O1 O 0.7983(2) 1.1729(4) 0.4237(2) 0.0855(10) Uani 1 1 d . . .
C2 C 0.8261(2) 1.0479(5) 0.3881(3) 0.0655(11) Uani 1 1 d . . .
C3 C 0.8350(2) 0.9123(6) 0.4340(3) 0.0693(12) Uani 1 1 d . . .
H4 H 0.8208 0.9140 0.4830 0.083 Uiso 1 1 calc R . .
C4 C 0.8643(3) 0.7793(5) 0.4067(3) 0.0650(11) Uani 1 1 d . . .
H5 H 0.8673 0.6898 0.4365 0.078 Uiso 1 1 calc R . .
C5 C 0.8452(2) 1.0433(5) 0.3159(3) 0.0607(10) Uani 1 1 d . . .
H6 H 0.8368 1.1298 0.2845 0.073 Uiso 1 1 calc R . .
C6 C 0.8781(2) 0.9062(5) 0.2883(2) 0.0546(9) Uani 1 1 d . . .
C7 C 0.8899(2) 0.7745(5) 0.3349(2) 0.0556(10) Uani 1 1 d . . .
C8 C 0.8914(2) 0.8996(5) 0.2091(2) 0.0585(10) Uani 1 1 d . . .
H7 H 0.8664 0.9710 0.1759 0.070 Uiso 1 1 calc R . .
O2 O 0.92185(15) 0.6437(3) 0.31225(16) 0.0577(7) Uani 1 1 d . . .
Mn1 Mn 1.0000 0.64823(10) 0.2500 0.0515(3) Uani 1 2 d S . .
N1 N 0.9357(2) 0.8008(4) 0.1819(2) 0.0594(8) Uani 1 1 d . . .
C9 C 0.9321(3) 0.7851(5) 0.0983(3) 0.0663(11) Uani 1 1 d . . .
H8 H 0.9821 0.7942 0.0825 0.080 Uiso 1 1 calc R . .
H9 H 0.9014 0.8680 0.0742 0.080 Uiso 1 1 calc R . .
C10 C 0.8987(3) 0.6271(6) 0.0740(3) 0.0782(14) Uani 1 1 d . . .
H10 H 0.8503 0.6172 0.0936 0.094 Uiso 1 1 calc R . .
H11 H 0.8898 0.6253 0.0191 0.094 Uiso 1 1 calc R . .
C11 C 0.9458(3) 0.4865(6) 0.0996(3) 0.0721(12) Uani 1 1 d . . .
H12 H 0.9242 0.3942 0.0741 0.087 Uiso 1 1 calc R . .
H13 H 0.9959 0.5001 0.0845 0.087 Uiso 1 1 calc R . .
C12 C 1.0080(3) 0.3198(6) 0.2934(3) 0.0752(13) Uani 1 1 d . . .
H14 H 0.9611 0.3153 0.3162 0.090 Uiso 1 1 calc R . .
H15 H 1.0376 0.2288 0.3098 0.090 Uiso 1 1 calc R . .
N2 N 1.0488(2) 0.4615(5) 0.3175(2) 0.0651(9) Uani 1 1 d D . .
H16 H 1.0906(19) 0.453(4) 0.306(2) 0.046(11) Uiso 1 1 d D . .
C13 C 0.4140(10) 1.4025(12) -0.0095(5) 0.244(9) Uani 1 1 d . . .
H17 H 0.4327 1.4231 0.0423 0.366 Uiso 1 1 calc R . .
H18 H 0.3760 1.4775 -0.0259 0.366 Uiso 1 1 calc R . .
H19 H 0.4544 1.4101 -0.0408 0.366 Uiso 1 1 calc R . .
O3 O 0.3890(4) 1.2795(7) -0.0142(3) 0.151(3) Uani 1 1 d . . .
C14 C 0.4116(4) 1.1516(7) 0.0290(3) 0.0936(18) Uani 1 1 d . . .
C15 C 0.4781(4) 1.1356(6) 0.0733(3) 0.0805(15) Uani 1 1 d . . .
H20 H 0.5130 1.2162 0.0752 0.097 Uiso 1 1 calc R . .
C16 C 0.4949(3) 0.9994(5) 0.1163(2) 0.0636(11) Uani 1 1 d . . .
C17 C 0.3619(3) 1.0280(8) 0.0230(3) 0.0926(17) Uani 1 1 d . . .
H21 H 0.3172 1.0368 -0.0083 0.111 Uiso 1 1 calc R . .
C18 C 0.3775(3) 0.8934(7) 0.0622(3) 0.0770(13) Uani 1 1 d . . .
H22 H 0.3434 0.8112 0.0563 0.092 Uiso 1 1 calc R . .
C19 C 0.4436(2) 0.8754(5) 0.1112(2) 0.0604(10) Uani 1 1 d . . .
O4 O 0.45557(17) 0.7417(3) 0.14964(18) 0.0630(8) Uani 1 1 d . . .
Mn2 Mn 0.5000 0.74220(10) 0.2500 0.0555(3) Uani 1 2 d S . .
C20 C 0.5675(3) 0.9827(5) 0.1575(3) 0.0673(11) Uani 1 1 d . . .
H23 H 0.6055 1.0480 0.1443 0.081 Uiso 1 1 calc R . .
N4 N 0.58434(19) 0.8841(4) 0.2117(2) 0.0616(9) Uani 1 1 d . . .
C21 C 0.6636(2) 0.8643(6) 0.2416(3) 0.0763(13) Uani 1 1 d . . .
H24 H 0.6689 0.8785 0.2962 0.092 Uiso 1 1 calc R . .
H25 H 0.6938 0.9429 0.2198 0.092 Uiso 1 1 calc R . .
C22 C 0.6916(3) 0.7021(7) 0.2227(3) 0.0844(15) Uani 1 1 d . . .
H26 H 0.6832 0.6874 0.1682 0.101 Uiso 1 1 calc R . .
H27 H 0.7454 0.6980 0.2369 0.101 Uiso 1 1 calc R . .
C23 C 0.6556(3) 0.5680(7) 0.2607(3) 0.0828(15) Uani 1 1 d . . .
H28 H 0.6839 0.4735 0.2538 0.099 Uiso 1 1 calc R . .
H29 H 0.6581 0.5886 0.3147 0.099 Uiso 1 1 calc R . .
N3 N 0.5752(2) 0.5419(5) 0.2302(2) 0.0683(10) Uani 1 1 d . . .
C24 C 0.5416(3) 0.4021(6) 0.2613(3) 0.0823(14) Uani 1 1 d . . .
H31 H 0.5515 0.4019 0.3162 0.099 Uiso 1 1 calc R . .
H32 H 0.5638 0.3089 0.2421 0.099 Uiso 1 1 calc R . .
Cl1 Cl 0.74756(6) 1.28652(14) 0.11925(7) 0.0664(3) Uani 1 1 d . . .
O5 O 0.67009(19) 1.3050(4) 0.1296(2) 0.0835(10) Uani 1 1 d . . .
O6 O 0.7626(2) 1.3607(5) 0.0506(2) 0.0935(12) Uani 1 1 d . . .
O7 O 0.7926(2) 1.3537(5) 0.1834(2) 0.0972(12) Uani 1 1 d . . .
O8 O 0.7634(3) 1.1249(5) 0.1140(3) 0.1024(13) Uani 1 1 d . . .
H33 H 0.573(2) 0.525(5) 0.182(3) 0.062(13) 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
C1 O1 1.430(7) . ?
C1 H1 0.9600 . ?
C1 H2 0.9600 . ?
C1 H3 0.9600 . ?
O1 C2 1.364(5) . ?
C2 C5 1.359(6) . ?
C2 C3 1.417(7) . ?
C3 C4 1.365(6) . ?
C3 H4 0.9300 . ?
C4 C7 1.398(6) . ?
C4 H5 0.9300 . ?
C5 C6 1.423(6) . ?
C5 H6 0.9300 . ?
C6 C7 1.401(6) . ?
C6 C8 1.451(6) . ?
C7 O2 1.339(5) . ?
C8 N1 1.288(5) . ?
C8 H7 0.9300 . ?
O2 Mn1 1.873(3) . ?
Mn1 O2 1.873(3) 2_755 ?
Mn1 N1 2.049(4) 2_755 ?
Mn1 N1 2.049(4) . ?
Mn1 N2 2.129(4) 2_755 ?
Mn1 N2 2.129(4) . ?
N1 C9 1.482(5) . ?
C9 C10 1.524(7) . ?
C9 H8 0.9700 . ?
C9 H9 0.9700 . ?
C10 C11 1.513(7) . ?
C10 H10 0.9700 . ?
C10 H11 0.9700 . ?
C11 N2 1.477(6) 2_755 ?
C11 H12 0.9700 . ?
C11 H13 0.9700 . ?
C12 N2 1.458(6) . ?
C12 C12 1.533(10) 2_755 ?
C12 H14 0.9700 . ?
C12 H15 0.9700 . ?
N2 C11 1.477(6) 2_755 ?
N2 H16 0.80(3) . ?
C13 O3 1.145(13) . ?
C13 H17 0.9600 . ?
C13 H18 0.9600 . ?
C13 H19 0.9600 . ?
O3 C14 1.372(7) . ?
C14 C15 1.363(9) . ?
C14 C17 1.380(9) . ?
C15 C16 1.410(6) . ?
C15 H20 0.9300 . ?
C16 C19 1.401(6) . ?
C16 C20 1.431(7) . ?
C17 C18 1.359(8) . ?
C17 H21 0.9300 . ?
C18 C19 1.402(6) . ?
C18 H22 0.9300 . ?
C19 O4 1.339(5) . ?
O4 Mn2 1.871(3) . ?
Mn2 O4 1.871(3) 2_655 ?
Mn2 N4 2.108(4) . ?
Mn2 N4 2.108(3) 2_655 ?
Mn2 N3 2.232(4) . ?
Mn2 N3 2.232(4) 2_655 ?
C20 N4 1.289(6) . ?
C20 H23 0.9300 . ?
N4 C21 1.473(5) . ?
C21 C22 1.527(8) . ?
C21 H24 0.9700 . ?
C21 H25 0.9700 . ?
C22 C23 1.511(8) . ?
C22 H26 0.9700 . ?
C22 H27 0.9700 . ?
C23 N3 1.502(6) . ?
C23 H28 0.9700 . ?
C23 H29 0.9700 . ?
N3 C24 1.473(6) . ?
N3 H33 0.87(4) . ?
C24 C24 1.504(11) 2_655 ?
C24 H31 0.9700 . ?
C24 H32 0.9700 . ?
Cl1 O8 1.418(4) . ?
Cl1 O6 1.423(4) . ?
Cl1 O5 1.429(4) . ?
Cl1 O7 1.443(4) . ?

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 C1 H1 109.5 . . ?
O1 C1 H2 109.5 . . ?
H1 C1 H2 109.5 . . ?
O1 C1 H3 109.5 . . ?
H1 C1 H3 109.5 . . ?
H2 C1 H3 109.5 . . ?
C2 O1 C1 116.7(4) . . ?
C5 C2 O1 126.8(4) . . ?
C5 C2 C3 119.5(4) . . ?
O1 C2 C3 113.7(4) . . ?
C4 C3 C2 120.3(4) . . ?
C4 C3 H4 119.8 . . ?
C2 C3 H4 119.8 . . ?
C3 C4 C7 121.6(4) . . ?
C3 C4 H5 119.2 . . ?
C7 C4 H5 119.2 . . ?
C2 C5 C6 120.1(4) . . ?
C2 C5 H6 119.9 . . ?
C6 C5 H6 119.9 . . ?
C7 C6 C5 120.3(4) . . ?
C7 C6 C8 120.6(4) . . ?
C5 C6 C8 118.8(4) . . ?
O2 C7 C4 119.3(4) . . ?
O2 C7 C6 122.7(4) . . ?
C4 C7 C6 117.9(4) . . ?
N1 C8 C6 123.9(4) . . ?
N1 C8 H7 118.0 . . ?
C6 C8 H7 118.0 . . ?
C7 O2 Mn1 122.0(2) . . ?
O2 Mn1 O2 177.62(17) 2_755 . ?
O2 Mn1 N1 87.17(13) 2_755 2_755 ?
O2 Mn1 N1 94.35(13) . 2_755 ?
O2 Mn1 N1 94.35(13) 2_755 . ?
O2 Mn1 N1 87.17(13) . . ?
N1 Mn1 N1 100.7(2) 2_755 . ?
O2 Mn1 N2 86.64(14) 2_755 2_755 ?
O2 Mn1 N2 91.57(15) . 2_755 ?
N1 Mn1 N2 169.13(15) 2_755 2_755 ?
N1 Mn1 N2 88.63(15) . 2_755 ?
O2 Mn1 N2 91.57(15) 2_755 . ?
O2 Mn1 N2 86.64(14) . . ?
N1 Mn1 N2 88.63(14) 2_755 . ?
N1 Mn1 N2 169.13(15) . . ?
N2 Mn1 N2 82.6(2) 2_755 . ?
C8 N1 C9 118.0(4) . . ?
C8 N1 Mn1 122.0(3) . . ?
C9 N1 Mn1 119.5(3) . . ?
N1 C9 C10 109.7(4) . . ?
N1 C9 H8 109.7 . . ?
C10 C9 H8 109.7 . . ?
N1 C9 H9 109.7 . . ?
C10 C9 H9 109.7 . . ?
H8 C9 H9 108.2 . . ?
C11 C10 C9 115.6(4) . . ?
C11 C10 H10 108.4 . . ?
C9 C10 H10 108.4 . . ?
C11 C10 H11 108.4 . . ?
C9 C10 H11 108.4 . . ?
H10 C10 H11 107.5 . . ?
N2 C11 C10 112.9(4) 2_755 . ?
N2 C11 H12 109.0 2_755 . ?
C10 C11 H12 109.0 . . ?
N2 C11 H13 109.0 2_755 . ?
C10 C11 H13 109.0 . . ?
H12 C11 H13 107.8 . . ?
N2 C12 C12 109.2(3) . 2_755 ?
N2 C12 H14 109.8 . . ?
C12 C12 H14 109.8 2_755 . ?
N2 C12 H15 109.8 . . ?
C12 C12 H15 109.8 2_755 . ?
H14 C12 H15 108.3 . . ?
C12 N2 C11 113.0(4) . 2_755 ?
C12 N2 Mn1 107.3(3) . . ?
C11 N2 Mn1 115.5(3) 2_755 . ?
C12 N2 H16 108(3) . . ?
C11 N2 H16 107(3) 2_755 . ?
Mn1 N2 H16 106(3) . . ?
O3 C13 H17 109.5 . . ?
O3 C13 H18 109.5 . . ?
H17 C13 H18 109.5 . . ?
O3 C13 H19 109.5 . . ?
H17 C13 H19 109.5 . . ?
H18 C13 H19 109.5 . . ?
C13 O3 C14 127.2(9) . . ?
C15 C14 O3 126.1(7) . . ?
C15 C14 C17 119.0(5) . . ?
O3 C14 C17 114.8(6) . . ?
C14 C15 C16 121.2(5) . . ?
C14 C15 H20 119.4 . . ?
C16 C15 H20 119.4 . . ?
C19 C16 C15 119.4(4) . . ?
C19 C16 C20 120.9(4) . . ?
C15 C16 C20 119.3(4) . . ?
C18 C17 C14 121.1(5) . . ?
C18 C17 H21 119.5 . . ?
C14 C17 H21 119.5 . . ?
C17 C18 C19 121.6(5) . . ?
C17 C18 H22 119.2 . . ?
C19 C18 H22 119.2 . . ?
O4 C19 C16 123.1(4) . . ?
O4 C19 C18 119.3(4) . . ?
C16 C19 C18 117.6(4) . . ?
C19 O4 Mn2 120.7(3) . . ?
O4 Mn2 O4 179.73(18) . 2_655 ?
O4 Mn2 N4 86.72(14) . . ?
O4 Mn2 N4 93.44(14) 2_655 . ?
O4 Mn2 N4 93.44(14) . 2_655 ?
O4 Mn2 N4 86.72(14) 2_655 2_655 ?
N4 Mn2 N4 109.5(2) . 2_655 ?
O4 Mn2 N3 93.01(15) . . ?
O4 Mn2 N3 86.78(14) 2_655 . ?
N4 Mn2 N3 85.84(15) . . ?
N4 Mn2 N3 163.63(16) 2_655 . ?
O4 Mn2 N3 86.78(14) . 2_655 ?
O4 Mn2 N3 93.01(15) 2_655 2_655 ?
N4 Mn2 N3 163.63(16) . 2_655 ?
N4 Mn2 N3 85.84(15) 2_655 2_655 ?
N3 Mn2 N3 79.5(2) . 2_655 ?
N4 C20 C16 125.0(4) . . ?
N4 C20 H23 117.5 . . ?
C16 C20 H23 117.5 . . ?
C20 N4 C21 119.0(4) . . ?
C20 N4 Mn2 119.9(3) . . ?
C21 N4 Mn2 121.0(3) . . ?
N4 C21 C22 110.7(4) . . ?
N4 C21 H24 109.5 . . ?
C22 C21 H24 109.5 . . ?
N4 C21 H25 109.5 . . ?
C22 C21 H25 109.5 . . ?
H24 C21 H25 108.1 . . ?
C23 C22 C21 115.3(4) . . ?
C23 C22 H26 108.4 . . ?
C21 C22 H26 108.4 . . ?
C23 C22 H27 108.4 . . ?
C21 C22 H27 108.4 . . ?
H26 C22 H27 107.5 . . ?
N3 C23 C22 113.1(4) . . ?
N3 C23 H28 109.0 . . ?
C22 C23 H28 109.0 . . ?
N3 C23 H29 109.0 . . ?
C22 C23 H29 109.0 . . ?
H28 C23 H29 107.8 . . ?
C24 N3 C23 113.7(4) . . ?
C24 N3 Mn2 106.8(3) . . ?
C23 N3 Mn2 113.7(3) . . ?
C24 N3 H33 105(3) . . ?
C23 N3 H33 108(3) . . ?
Mn2 N3 H33 109(3) . . ?
N3 C24 C24 109.4(4) . 2_655 ?
N3 C24 H31 109.8 . . ?
C24 C24 H31 109.8 2_655 . ?
N3 C24 H32 109.8 . . ?
C24 C24 H32 109.8 2_655 . ?
H31 C24 H32 108.2 . . ?
O8 Cl1 O6 108.8(3) . . ?
O8 Cl1 O5 108.7(3) . . ?
O6 Cl1 O5 109.5(3) . . ?
O8 Cl1 O7 110.0(3) . . ?
O6 Cl1 O7 110.8(3) . . ?
O5 Cl1 O7 109.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.017
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.075
####################################################################### 
# 
# 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_p21n
_database_code_depnum_ccdc_archive 'CCDC 1441063'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H32 Mn N5 O7'
_chemical_formula_weight         557.49

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'
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'
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   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   8.1183(16)
_cell_length_b                   15.286(3)
_cell_length_c                   20.484(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.528(4)
_cell_angle_gamma                90.00
_cell_volume                     2499.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9958
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      28.37

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_T_max  0.932
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32268
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         28.37
_reflns_number_total             5901
_reflns_number_gt                5649
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0000P)²+7.3975P] 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         5901
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1382
_refine_ls_wR_factor_gt          0.1362
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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
C1 C 0.7679(6) 0.6208(3) 0.4379(2) 0.0625(13) Uani 1 1 d . . .
H1 H 0.7970 0.5979 0.4832 0.094 Uiso 1 1 calc R . .
H2 H 0.8193 0.6785 0.4358 0.094 Uiso 1 1 calc R . .
H3 H 0.8093 0.5808 0.4072 0.094 Uiso 1 1 calc R . .
O1 O 0.5906(5) 0.62849(17) 0.41986(13) 0.0597(9) Uani 1 1 d . . .
C2 C 0.5026(5) 0.5516(2) 0.41330(15) 0.0415(8) Uani 1 1 d . . .
C3 C 0.3332(6) 0.5596(2) 0.39006(16) 0.0446(9) Uani 1 1 d . . .
H4 H 0.2862 0.6161 0.3804 0.054 Uiso 1 1 calc R . .
C4 C 0.2307(5) 0.4874(2) 0.38050(16) 0.0368(7) Uani 1 1 d . . .
H5 H 0.1141 0.4947 0.3643 0.044 Uiso 1 1 calc R . .
C5 C 0.2960(4) 0.40303(17) 0.39432(13) 0.0251(5) Uani 1 1 d . . .
C6 C 0.5699(4) 0.4711(2) 0.42916(15) 0.0347(7) Uani 1 1 d . . .
H6 H 0.6861 0.4656 0.4466 0.042 Uiso 1 1 calc R . .
C7 C 0.4680(4) 0.39565(18) 0.41983(13) 0.0262(5) Uani 1 1 d . . .
C8 C 0.5403(3) 0.31345(19) 0.44440(13) 0.0252(5) Uani 1 1 d . . .
H7 H 0.6459 0.3149 0.4735 0.030 Uiso 1 1 calc R . .
N1 N 0.4731(3) 0.23854(15) 0.43005(11) 0.0215(4) Uani 1 1 d . . .
C9 C 0.5481(3) 0.16284(19) 0.46916(13) 0.0262(5) Uani 1 1 d . . .
H8 H 0.6609 0.1788 0.4935 0.031 Uiso 1 1 calc R . .
H9 H 0.5608 0.1139 0.4388 0.031 Uiso 1 1 calc R . .
C10 C 0.4398(4) 0.1335(2) 0.51847(14) 0.0323(6) Uani 1 1 d . . .
H10 H 0.5039 0.0901 0.5489 0.039 Uiso 1 1 calc R . .
H11 H 0.4195 0.1846 0.5456 0.039 Uiso 1 1 calc R . .
C11 C 0.2722(4) 0.0936(2) 0.48883(15) 0.0308(6) Uani 1 1 d . . .
H12 H 0.2897 0.0451 0.4589 0.037 Uiso 1 1 calc R . .
H13 H 0.2199 0.0691 0.5248 0.037 Uiso 1 1 calc R . .
N2 N 0.1585(3) 0.15870(16) 0.45136(12) 0.0247(5) Uani 1 1 d . . .
H14 H 0.142(6) 0.199(3) 0.475(2) 0.048(12) Uiso 1 1 d . . .
C12 C -0.0079(4) 0.12335(19) 0.42443(15) 0.0287(6) Uani 1 1 d . . .
H15 H -0.0686 0.1103 0.4610 0.034 Uiso 1 1 calc R . .
H16 H 0.0030 0.0684 0.3999 0.034 Uiso 1 1 calc R . .
C13 C -0.1033(3) 0.1906(2) 0.37824(15) 0.0292(6) Uani 1 1 d . . .
H17 H -0.2180 0.1690 0.3610 0.035 Uiso 1 1 calc R . .
H18 H -0.1123 0.2457 0.4027 0.035 Uiso 1 1 calc R . .
N3 N -0.0150(3) 0.20685(16) 0.32258(12) 0.0249(5) Uani 1 1 d . . .
H19 H -0.022(4) 0.165(2) 0.2999(18) 0.028(9) Uiso 1 1 d . . .
C14 C -0.0905(3) 0.27903(19) 0.27901(15) 0.0298(6) Uani 1 1 d . . .
H20 H -0.0744 0.3347 0.3041 0.036 Uiso 1 1 calc R . .
H21 H -0.2125 0.2687 0.2661 0.036 Uiso 1 1 calc R . .
C15 C -0.0151(4) 0.28760(19) 0.21693(15) 0.0298(6) Uani 1 1 d . . .
H22 H -0.0881 0.3260 0.1851 0.036 Uiso 1 1 calc R . .
H23 H -0.0141 0.2292 0.1961 0.036 Uiso 1 1 calc R . .
C16 C 0.1612(3) 0.32424(18) 0.22871(14) 0.0268(5) Uani 1 1 d . . .
H24 H 0.1946 0.3375 0.1857 0.032 Uiso 1 1 calc R . .
H25 H 0.1655 0.3792 0.2545 0.032 Uiso 1 1 calc R . .
N4 N 0.2773(3) 0.25976(14) 0.26542(11) 0.0214(4) Uani 1 1 d . . .
C17 C 0.3753(3) 0.22046(17) 0.23313(12) 0.0219(5) Uani 1 1 d . . .
H26 H 0.3821 0.2412 0.1900 0.026 Uiso 1 1 calc R . .
C18 C 0.4771(3) 0.14573(16) 0.25887(12) 0.0197(5) Uani 1 1 d . . .
C19 C 0.6134(3) 0.12400(17) 0.22913(13) 0.0226(5) Uani 1 1 d . . .
H27 H 0.6358 0.1575 0.1927 0.027 Uiso 1 1 calc R . .
C20 C 0.7156(3) 0.05435(18) 0.25218(13) 0.0236(5) Uani 1 1 d . . .
O3 O 0.8565(3) 0.04411(14) 0.22473(11) 0.0329(5) Uani 1 1 d . . .
C21 C 0.9609(4) -0.0294(2) 0.24561(16) 0.0368(7) Uani 1 1 d . . .
H28 H 0.9985 -0.0271 0.2938 0.055 Uiso 1 1 calc R . .
H29 H 1.0584 -0.0281 0.2236 0.055 Uiso 1 1 calc R . .
H30 H 0.8976 -0.0834 0.2337 0.055 Uiso 1 1 calc R . .
C22 C 0.6750(4) 0.00134(17) 0.30200(13) 0.0249(5) Uani 1 1 d . . .
H31 H 0.7432 -0.0476 0.3174 0.030 Uiso 1 1 calc R . .
C23 C 0.5344(4) 0.02027(17) 0.32912(13) 0.0246(5) Uani 1 1 d . . .
H32 H 0.5049 -0.0180 0.3617 0.029 Uiso 1 1 calc R . .
C24 C 0.4351(3) 0.09356(16) 0.31015(12) 0.0200(5) Uani 1 1 d . . .
O2 O 0.3052(2) 0.11003(12) 0.33993(9) 0.0219(4) Uani 1 1 d . . .
Mn1 Mn 0.25057(5) 0.22238(2) 0.364382(19) 0.01829(12) Uani 1 1 d . . .
O4 O 0.1923(2) 0.33475(12) 0.38671(10) 0.0247(4) Uani 1 1 d . . .
N5 N 0.4719(3) 0.32577(16) 0.09162(12) 0.0288(5) Uani 1 1 d . . .
O5 O 0.3867(5) 0.3922(2) 0.09120(17) 0.0715(10) Uani 1 1 d . . .
O6 O 0.4140(4) 0.26071(18) 0.05950(18) 0.0667(10) Uani 1 1 d . . .
O7 O 0.6140(3) 0.3224(2) 0.12418(17) 0.0613(8) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.424(6) . ?
C1 H1 0.9800 . ?
C1 H2 0.9800 . ?
C1 H3 0.9800 . ?
O1 C2 1.370(4) . ?
C2 C6 1.361(5) . ?
C2 C3 1.376(6) . ?
C3 C4 1.375(5) . ?
C3 H4 0.9500 . ?
C4 C5 1.404(4) . ?
C4 H5 0.9500 . ?
C5 O4 1.332(3) . ?
C5 C7 1.403(4) . ?
C6 C7 1.411(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.438(4) . ?
C8 N1 1.279(3) . ?
C8 H7 0.9500 . ?
N1 C9 1.474(3) . ?
N1 Mn1 2.060(2) . ?
C9 C10 1.523(4) . ?
C9 H8 0.9900 . ?
C9 H9 0.9900 . ?
C10 C11 1.512(4) . ?
C10 H10 0.9900 . ?
C10 H11 0.9900 . ?
C11 N2 1.473(4) . ?
C11 H12 0.9900 . ?
C11 H13 0.9900 . ?
N2 C12 1.466(4) . ?
N2 Mn1 2.273(2) . ?
N2 H14 0.81(5) . ?
C12 C13 1.511(4) . ?
C12 H15 0.9900 . ?
C12 H16 0.9900 . ?
C13 N3 1.475(4) . ?
C13 H17 0.9900 . ?
C13 H18 0.9900 . ?
N3 C14 1.480(4) . ?
N3 Mn1 2.182(2) . ?
N3 H19 0.78(4) . ?
C14 C15 1.514(4) . ?
C14 H20 0.9900 . ?
C14 H21 0.9900 . ?
C15 C16 1.515(4) . ?
C15 H22 0.9900 . ?
C15 H23 0.9900 . ?
C16 N4 1.471(3) . ?
C16 H24 0.9900 . ?
C16 H25 0.9900 . ?
N4 C17 1.274(3) . ?
N4 Mn1 2.155(2) . ?
C17 C18 1.451(4) . ?
C17 H26 0.9500 . ?
C18 C19 1.397(4) . ?
C18 C24 1.409(3) . ?
C19 C20 1.379(4) . ?
C19 H27 0.9500 . ?
C20 O3 1.372(3) . ?
C20 C22 1.389(4) . ?
O3 C21 1.425(4) . ?
C21 H28 0.9800 . ?
C21 H29 0.9800 . ?
C21 H30 0.9800 . ?
C22 C23 1.389(4) . ?
C22 H31 0.9500 . ?
C23 C24 1.393(4) . ?
C23 H32 0.9500 . ?
C24 O2 1.335(3) . ?
O2 Mn1 1.8650(19) . ?
Mn1 O4 1.8607(19) . ?
N5 O7 1.223(4) . ?
N5 O5 1.228(4) . ?
N5 O6 1.237(4) . ?

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 C1 H1 109.5 . . ?
O1 C1 H2 109.5 . . ?
H1 C1 H2 109.5 . . ?
O1 C1 H3 109.5 . . ?
H1 C1 H3 109.5 . . ?
H2 C1 H3 109.5 . . ?
C2 O1 C1 116.1(3) . . ?
C6 C2 O1 125.0(4) . . ?
C6 C2 C3 119.7(3) . . ?
O1 C2 C3 115.3(3) . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H4 119.4 . . ?
C2 C3 H4 119.4 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H5 119.6 . . ?
C5 C4 H5 119.6 . . ?
O4 C5 C7 123.0(2) . . ?
O4 C5 C4 119.3(3) . . ?
C7 C5 C4 117.6(3) . . ?
C2 C6 C7 120.4(3) . . ?
C2 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C5 C7 C6 120.2(3) . . ?
C5 C7 C8 121.0(2) . . ?
C6 C7 C8 118.3(3) . . ?
N1 C8 C7 124.9(2) . . ?
N1 C8 H7 117.6 . . ?
C7 C8 H7 117.6 . . ?
C8 N1 C9 117.5(2) . . ?
C8 N1 Mn1 122.94(19) . . ?
C9 N1 Mn1 119.10(17) . . ?
N1 C9 C10 111.1(2) . . ?
N1 C9 H8 109.4 . . ?
C10 C9 H8 109.4 . . ?
N1 C9 H9 109.4 . . ?
C10 C9 H9 109.4 . . ?
H8 C9 H9 108.0 . . ?
C11 C10 C9 116.0(2) . . ?
C11 C10 H10 108.3 . . ?
C9 C10 H10 108.3 . . ?
C11 C10 H11 108.3 . . ?
C9 C10 H11 108.3 . . ?
H10 C10 H11 107.4 . . ?
N2 C11 C10 111.7(2) . . ?
N2 C11 H12 109.3 . . ?
C10 C11 H12 109.3 . . ?
N2 C11 H13 109.3 . . ?
C10 C11 H13 109.3 . . ?
H12 C11 H13 107.9 . . ?
C12 N2 C11 113.2(2) . . ?
C12 N2 Mn1 105.97(17) . . ?
C11 N2 Mn1 115.66(17) . . ?
C12 N2 H14 105(3) . . ?
C11 N2 H14 111(3) . . ?
Mn1 N2 H14 105(3) . . ?
N2 C12 C13 108.5(2) . . ?
N2 C12 H15 110.0 . . ?
C13 C12 H15 110.0 . . ?
N2 C12 H16 110.0 . . ?
C13 C12 H16 110.0 . . ?
H15 C12 H16 108.4 . . ?
N3 C13 C12 109.4(2) . . ?
N3 C13 H17 109.8 . . ?
C12 C13 H17 109.8 . . ?
N3 C13 H18 109.8 . . ?
C12 C13 H18 109.8 . . ?
H17 C13 H18 108.2 . . ?
C13 N3 C14 112.7(2) . . ?
C13 N3 Mn1 107.46(17) . . ?
C14 N3 Mn1 115.23(17) . . ?
C13 N3 H19 109(3) . . ?
C14 N3 H19 106(3) . . ?
Mn1 N3 H19 107(3) . . ?
N3 C14 C15 112.6(2) . . ?
N3 C14 H20 109.1 . . ?
C15 C14 H20 109.1 . . ?
N3 C14 H21 109.1 . . ?
C15 C14 H21 109.1 . . ?
H20 C14 H21 107.8 . . ?
C14 C15 C16 114.4(2) . . ?
C14 C15 H22 108.7 . . ?
C16 C15 H22 108.7 . . ?
C14 C15 H23 108.7 . . ?
C16 C15 H23 108.7 . . ?
H22 C15 H23 107.6 . . ?
N4 C16 C15 109.4(2) . . ?
N4 C16 H24 109.8 . . ?
C15 C16 H24 109.8 . . ?
N4 C16 H25 109.8 . . ?
C15 C16 H25 109.8 . . ?
H24 C16 H25 108.2 . . ?
C17 N4 C16 116.9(2) . . ?
C17 N4 Mn1 122.88(17) . . ?
C16 N4 Mn1 119.55(17) . . ?
N4 C17 C18 123.4(2) . . ?
N4 C17 H26 118.3 . . ?
C18 C17 H26 118.3 . . ?
C19 C18 C24 120.6(2) . . ?
C19 C18 C17 118.2(2) . . ?
C24 C18 C17 121.1(2) . . ?
C20 C19 C18 120.6(2) . . ?
C20 C19 H27 119.7 . . ?
C18 C19 H27 119.7 . . ?
O3 C20 C19 116.3(2) . . ?
O3 C20 C22 124.2(2) . . ?
C19 C20 C22 119.5(2) . . ?
C20 O3 C21 117.5(2) . . ?
O3 C21 H28 109.5 . . ?
O3 C21 H29 109.5 . . ?
H28 C21 H29 109.5 . . ?
O3 C21 H30 109.5 . . ?
H28 C21 H30 109.5 . . ?
H29 C21 H30 109.5 . . ?
C23 C22 C20 119.7(2) . . ?
C23 C22 H31 120.2 . . ?
C20 C22 H31 120.2 . . ?
C22 C23 C24 122.2(2) . . ?
C22 C23 H32 118.9 . . ?
C24 C23 H32 118.9 . . ?
O2 C24 C23 119.3(2) . . ?
O2 C24 C18 123.6(2) . . ?
C23 C24 C18 117.1(2) . . ?
C24 O2 Mn1 122.87(15) . . ?
O4 Mn1 O2 178.54(9) . . ?
O4 Mn1 N1 87.75(9) . . ?
O2 Mn1 N1 93.59(9) . . ?
O4 Mn1 N4 93.45(9) . . ?
O2 Mn1 N4 85.52(8) . . ?
N1 Mn1 N4 110.82(9) . . ?
O4 Mn1 N3 85.40(9) . . ?
O2 Mn1 N3 93.48(9) . . ?
N1 Mn1 N3 162.66(9) . . ?
N4 Mn1 N3 85.51(9) . . ?
O4 Mn1 N2 93.90(9) . . ?
O2 Mn1 N2 86.82(8) . . ?
N1 Mn1 N2 85.08(9) . . ?
N4 Mn1 N2 162.73(9) . . ?
N3 Mn1 N2 79.53(9) . . ?
C5 O4 Mn1 124.65(18) . . ?
O7 N5 O5 120.8(3) . . ?
O7 N5 O6 119.0(3) . . ?
O5 N5 O6 120.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.943
_diffrn_reflns_theta_full        28.37
_diffrn_measured_fraction_theta_full 0.943
_refine_diff_density_max         0.756
_refine_diff_density_min         -0.873
_refine_diff_density_rms         0.080
####################################################################### 
# 
# 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_181
_database_code_depnum_ccdc_archive 'CCDC 1441064'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H32 Mn N5 O7'
_chemical_formula_weight         557.49

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'
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'
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   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   8.1744(9)
_cell_length_b                   15.4164(17)
_cell_length_c                   20.726(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.763(2)
_cell_angle_gamma                90.00
_cell_volume                     2565.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9779
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      28.35

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    0.568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29287
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.28
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4765
_reflns_number_gt                4525
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0000P)²+5.4772P] 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         4765
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0598
_refine_ls_wR_factor_ref         0.1318
_refine_ls_wR_factor_gt          0.1305
_refine_ls_goodness_of_fit_ref   1.230
_refine_ls_restrained_S_all      1.230
_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
C1 C 1.0423(4) 0.1886(2) 0.44468(16) 0.0335(7) Uani 1 1 d . . .
H1 H 1.1473 0.1873 0.4735 0.040 Uiso 1 1 calc R . .
C2 C 0.9703(4) 0.1067(2) 0.42031(15) 0.0336(7) Uani 1 1 d . . .
C3 C 1.0706(5) 0.0318(2) 0.42980(18) 0.0462(9) Uani 1 1 d . . .
H2 H 1.1859 0.0369 0.4478 0.055 Uiso 1 1 calc R . .
C4 C 1.0027(7) -0.0486(2) 0.41324(19) 0.0563(12) Uani 1 1 d . . .
C5 C 1.2671(9) -0.1186(4) 0.4382(3) 0.091(2) Uani 1 1 d . . .
H3 H 1.3086 -0.0775 0.4089 0.136 Uiso 1 1 calc R . .
H4 H 1.3172 -0.1757 0.4343 0.136 Uiso 1 1 calc R . .
H5 H 1.2971 -0.0981 0.4836 0.136 Uiso 1 1 calc R . .
O1 O 1.0915(6) -0.1250(2) 0.42021(17) 0.0827(12) Uani 1 1 d . . .
C6 C 0.8344(7) -0.0562(3) 0.3892(2) 0.0610(12) Uani 1 1 d . . .
H6 H 0.7873 -0.1120 0.3791 0.073 Uiso 1 1 calc R . .
C7 C 0.7333(6) 0.0159(2) 0.37972(19) 0.0500(10) Uani 1 1 d . . .
H7 H 0.6174 0.0091 0.3633 0.060 Uiso 1 1 calc R . .
C8 C 0.7992(4) 0.0997(2) 0.39395(15) 0.0341(7) Uani 1 1 d . . .
O2 O 0.6951(3) 0.16740(14) 0.38600(11) 0.0336(5) Uani 1 1 d . . .
N1 N 0.9753(3) 0.26312(17) 0.43038(12) 0.0297(6) Uani 1 1 d . . .
C9 C 1.0505(4) 0.3385(2) 0.46927(17) 0.0360(7) Uani 1 1 d . . .
H8 H 1.0629 0.3871 0.4394 0.043 Uiso 1 1 calc R . .
H9 H 1.1627 0.3226 0.4935 0.043 Uiso 1 1 calc R . .
C10 C 0.9423(5) 0.3672(3) 0.51788(19) 0.0473(9) Uani 1 1 d . . .
H10 H 0.9219 0.3162 0.5443 0.057 Uiso 1 1 calc R . .
H11 H 1.0059 0.4100 0.5483 0.057 Uiso 1 1 calc R . .
C11 C 0.7756(5) 0.4070(2) 0.4882(2) 0.0459(9) Uani 1 1 d . . .
H12 H 0.7233 0.4312 0.5237 0.055 Uiso 1 1 calc R . .
H13 H 0.7932 0.4552 0.4587 0.055 Uiso 1 1 calc R . .
N2 N 0.6620(3) 0.34208(19) 0.45046(15) 0.0351(6) Uani 1 1 d . . .
H14 H 0.642(5) 0.302(3) 0.476(2) 0.044(11) Uiso 1 1 d . . .
C12 C 0.4964(4) 0.3776(2) 0.42363(19) 0.0434(9) Uani 1 1 d . . .
H15 H 0.5076 0.4320 0.3994 0.052 Uiso 1 1 calc R . .
H16 H 0.4365 0.3909 0.4598 0.052 Uiso 1 1 calc R . .
C13 C 0.3999(4) 0.3113(3) 0.37790(19) 0.0429(8) Uani 1 1 d . . .
H17 H 0.3911 0.2565 0.4019 0.051 Uiso 1 1 calc R . .
H18 H 0.2859 0.3330 0.3610 0.051 Uiso 1 1 calc R . .
N3 N 0.4866(3) 0.29550(19) 0.32277(16) 0.0358(6) Uani 1 1 d . . .
H19 H 0.483(5) 0.340(3) 0.300(2) 0.047(12) Uiso 1 1 d . . .
C14 C 0.4108(4) 0.2238(2) 0.2792(2) 0.0435(9) Uani 1 1 d . . .
H20 H 0.2896 0.2342 0.2663 0.052 Uiso 1 1 calc R . .
H21 H 0.4266 0.1685 0.3039 0.052 Uiso 1 1 calc R . .
C15 C 0.4853(4) 0.2156(2) 0.21801(19) 0.0434(9) Uani 1 1 d . . .
H22 H 0.4863 0.2736 0.1975 0.052 Uiso 1 1 calc R . .
H23 H 0.4130 0.1775 0.1864 0.052 Uiso 1 1 calc R . .
C16 C 0.6623(4) 0.1790(2) 0.23035(17) 0.0375(8) Uani 1 1 d . . .
H24 H 0.6667 0.1250 0.2564 0.045 Uiso 1 1 calc R . .
H25 H 0.6954 0.1651 0.1880 0.045 Uiso 1 1 calc R . .
N4 N 0.7775(3) 0.24341(16) 0.26614(13) 0.0298(6) Uani 1 1 d . . .
C17 C 0.8752(4) 0.2829(2) 0.23490(15) 0.0297(6) Uani 1 1 d . . .
H26 H 0.8822 0.2624 0.1923 0.036 Uiso 1 1 calc R . .
C18 C 0.9765(4) 0.35709(19) 0.26000(14) 0.0258(6) Uani 1 1 d . . .
C19 C 1.1115(4) 0.3798(2) 0.23025(15) 0.0310(7) Uani 1 1 d . . .
H27 H 1.1335 0.3468 0.1941 0.037 Uiso 1 1 calc R . .
C20 C 1.2125(4) 0.4492(2) 0.25282(16) 0.0321(7) Uani 1 1 d . . .
O3 O 1.3513(3) 0.45988(18) 0.22478(14) 0.0507(7) Uani 1 1 d . . .
C21 C 1.4561(5) 0.5323(3) 0.2455(2) 0.0545(11) Uani 1 1 d . . .
H28 H 1.3927 0.5860 0.2351 0.082 Uiso 1 1 calc R . .
H29 H 1.5508 0.5318 0.2227 0.082 Uiso 1 1 calc R . .
H30 H 1.4968 0.5289 0.2930 0.082 Uiso 1 1 calc R . .
C22 C 1.1742(4) 0.5010(2) 0.30246(17) 0.0345(7) Uani 1 1 d . . .
H31 H 1.2422 0.5495 0.3178 0.041 Uiso 1 1 calc R . .
C23 C 1.0356(4) 0.48154(19) 0.32984(17) 0.0339(7) Uani 1 1 d . . .
H32 H 1.0070 0.5192 0.3623 0.041 Uiso 1 1 calc R . .
C24 C 0.9372(4) 0.40855(18) 0.31116(15) 0.0265(6) Uani 1 1 d . . .
O4 O 0.8086(3) 0.39178(13) 0.34093(11) 0.0309(5) Uani 1 1 d . . .
Mn1 Mn 0.75345(5) 0.27967(3) 0.36445(2) 0.02561(15) Uani 1 1 d . . .
N5 N 0.9739(4) 0.1772(2) 0.09218(15) 0.0445(7) Uani 1 1 d . . .
O5 O 1.1136(4) 0.1803(3) 0.1234(3) 0.1025(15) Uani 1 1 d . . .
O6 O 0.9170(5) 0.2395(2) 0.0600(3) 0.1108(18) Uani 1 1 d . . .
O7 O 0.8899(6) 0.1125(3) 0.0931(2) 0.1181(18) 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
C1 N1 1.283(4) . ?
C1 C2 1.444(5) . ?
C1 H1 0.9500 . ?
C2 C8 1.408(5) . ?
C2 C3 1.408(5) . ?
C3 C4 1.376(6) . ?
C3 H2 0.9500 . ?
C4 O1 1.377(5) . ?
C4 C6 1.378(7) . ?
C5 O1 1.418(8) . ?
C5 H3 0.9800 . ?
C5 H4 0.9800 . ?
C5 H5 0.9800 . ?
C6 C7 1.377(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.410(5) . ?
C7 H7 0.9500 . ?
C8 O2 1.337(4) . ?
O2 Mn1 1.872(2) . ?
N1 C9 1.480(4) . ?
N1 Mn1 2.072(3) . ?
C9 C10 1.525(5) . ?
C9 H8 0.9900 . ?
C9 H9 0.9900 . ?
C10 C11 1.517(6) . ?
C10 H10 0.9900 . ?
C10 H11 0.9900 . ?
C11 N2 1.484(5) . ?
C11 H12 0.9900 . ?
C11 H13 0.9900 . ?
N2 C12 1.470(4) . ?
N2 Mn1 2.272(3) . ?
N2 H14 0.86(4) . ?
C12 C13 1.512(5) . ?
C12 H15 0.9900 . ?
C12 H16 0.9900 . ?
C13 N3 1.473(5) . ?
C13 H17 0.9900 . ?
C13 H18 0.9900 . ?
N3 C14 1.487(5) . ?
N3 Mn1 2.204(3) . ?
N3 H19 0.83(4) . ?
C14 C15 1.512(6) . ?
C14 H20 0.9900 . ?
C14 H21 0.9900 . ?
C15 C16 1.529(5) . ?
C15 H22 0.9900 . ?
C15 H23 0.9900 . ?
C16 N4 1.470(4) . ?
C16 H24 0.9900 . ?
C16 H25 0.9900 . ?
N4 C17 1.273(4) . ?
N4 Mn1 2.157(3) . ?
C17 C18 1.451(4) . ?
C17 H26 0.9500 . ?
C18 C19 1.405(4) . ?
C18 C24 1.408(4) . ?
C19 C20 1.379(4) . ?
C19 H27 0.9500 . ?
C20 O3 1.378(4) . ?
C20 C22 1.383(5) . ?
O3 C21 1.423(4) . ?
C21 H28 0.9800 . ?
C21 H29 0.9800 . ?
C21 H30 0.9800 . ?
C22 C23 1.391(5) . ?
C22 H31 0.9500 . ?
C23 C24 1.395(4) . ?
C23 H32 0.9500 . ?
C24 O4 1.340(4) . ?
O4 Mn1 1.874(2) . ?
N5 O5 1.203(4) . ?
N5 O6 1.210(5) . ?
N5 O7 1.214(5) . ?

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
N1 C1 C2 125.0(3) . . ?
N1 C1 H1 117.5 . . ?
C2 C1 H1 117.5 . . ?
C8 C2 C3 120.1(3) . . ?
C8 C2 C1 120.9(3) . . ?
C3 C2 C1 118.7(3) . . ?
C4 C3 C2 120.5(4) . . ?
C4 C3 H2 119.8 . . ?
C2 C3 H2 119.8 . . ?
C3 C4 O1 124.4(5) . . ?
C3 C4 C6 119.7(4) . . ?
O1 C4 C6 115.9(4) . . ?
O1 C5 H3 109.5 . . ?
O1 C5 H4 109.5 . . ?
H3 C5 H4 109.5 . . ?
O1 C5 H5 109.5 . . ?
H3 C5 H5 109.5 . . ?
H4 C5 H5 109.5 . . ?
C4 O1 C5 117.1(4) . . ?
C7 C6 C4 121.0(4) . . ?
C7 C6 H6 119.5 . . ?
C4 C6 H6 119.5 . . ?
C6 C7 C8 120.9(4) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
O2 C8 C2 123.5(3) . . ?
O2 C8 C7 118.7(3) . . ?
C2 C8 C7 117.7(3) . . ?
C8 O2 Mn1 124.5(2) . . ?
C1 N1 C9 117.4(3) . . ?
C1 N1 Mn1 123.1(2) . . ?
C9 N1 Mn1 119.1(2) . . ?
N1 C9 C10 110.7(3) . . ?
N1 C9 H8 109.5 . . ?
C10 C9 H8 109.5 . . ?
N1 C9 H9 109.5 . . ?
C10 C9 H9 109.5 . . ?
H8 C9 H9 108.1 . . ?
C11 C10 C9 115.9(3) . . ?
C11 C10 H10 108.3 . . ?
C9 C10 H10 108.3 . . ?
C11 C10 H11 108.3 . . ?
C9 C10 H11 108.3 . . ?
H10 C10 H11 107.4 . . ?
N2 C11 C10 111.6(3) . . ?
N2 C11 H12 109.3 . . ?
C10 C11 H12 109.3 . . ?
N2 C11 H13 109.3 . . ?
C10 C11 H13 109.3 . . ?
H12 C11 H13 108.0 . . ?
C12 N2 C11 112.9(3) . . ?
C12 N2 Mn1 106.0(2) . . ?
C11 N2 Mn1 115.7(2) . . ?
C12 N2 H14 104(3) . . ?
C11 N2 H14 110(3) . . ?
Mn1 N2 H14 108(3) . . ?
N2 C12 C13 108.7(3) . . ?
N2 C12 H15 109.9 . . ?
C13 C12 H15 109.9 . . ?
N2 C12 H16 109.9 . . ?
C13 C12 H16 109.9 . . ?
H15 C12 H16 108.3 . . ?
N3 C13 C12 109.1(3) . . ?
N3 C13 H17 109.9 . . ?
C12 C13 H17 109.9 . . ?
N3 C13 H18 109.9 . . ?
C12 C13 H18 109.9 . . ?
H17 C13 H18 108.3 . . ?
C13 N3 C14 112.8(3) . . ?
C13 N3 Mn1 107.4(2) . . ?
C14 N3 Mn1 115.2(2) . . ?
C13 N3 H19 110(3) . . ?
C14 N3 H19 108(3) . . ?
Mn1 N3 H19 104(3) . . ?
N3 C14 C15 112.6(3) . . ?
N3 C14 H20 109.1 . . ?
C15 C14 H20 109.1 . . ?
N3 C14 H21 109.1 . . ?
C15 C14 H21 109.1 . . ?
H20 C14 H21 107.8 . . ?
C14 C15 C16 114.0(3) . . ?
C14 C15 H22 108.7 . . ?
C16 C15 H22 108.7 . . ?
C14 C15 H23 108.7 . . ?
C16 C15 H23 108.7 . . ?
H22 C15 H23 107.6 . . ?
N4 C16 C15 109.4(3) . . ?
N4 C16 H24 109.8 . . ?
C15 C16 H24 109.8 . . ?
N4 C16 H25 109.8 . . ?
C15 C16 H25 109.8 . . ?
H24 C16 H25 108.2 . . ?
C17 N4 C16 118.0(3) . . ?
C17 N4 Mn1 122.2(2) . . ?
C16 N4 Mn1 119.2(2) . . ?
N4 C17 C18 124.4(3) . . ?
N4 C17 H26 117.8 . . ?
C18 C17 H26 117.8 . . ?
C19 C18 C24 119.9(3) . . ?
C19 C18 C17 118.8(3) . . ?
C24 C18 C17 121.3(3) . . ?
C20 C19 C18 120.9(3) . . ?
C20 C19 H27 119.5 . . ?
C18 C19 H27 119.5 . . ?
O3 C20 C19 115.9(3) . . ?
O3 C20 C22 124.3(3) . . ?
C19 C20 C22 119.7(3) . . ?
C20 O3 C21 117.6(3) . . ?
O3 C21 H28 109.5 . . ?
O3 C21 H29 109.5 . . ?
H28 C21 H29 109.5 . . ?
O3 C21 H30 109.5 . . ?
H28 C21 H30 109.5 . . ?
H29 C21 H30 109.5 . . ?
C20 C22 C23 119.6(3) . . ?
C20 C22 H31 120.2 . . ?
C23 C22 H31 120.2 . . ?
C22 C23 C24 122.1(3) . . ?
C22 C23 H32 118.9 . . ?
C24 C23 H32 118.9 . . ?
O4 C24 C23 119.3(3) . . ?
O4 C24 C18 123.1(3) . . ?
C23 C24 C18 117.6(3) . . ?
C24 O4 Mn1 123.06(18) . . ?
O2 Mn1 O4 178.65(10) . . ?
O2 Mn1 N1 87.67(10) . . ?
O4 Mn1 N1 93.53(10) . . ?
O2 Mn1 N4 93.33(10) . . ?
O4 Mn1 N4 85.66(10) . . ?
N1 Mn1 N4 111.59(10) . . ?
O2 Mn1 N3 85.31(10) . . ?
O4 Mn1 N3 93.71(10) . . ?
N1 Mn1 N3 162.15(11) . . ?
N4 Mn1 N3 85.23(11) . . ?
O2 Mn1 N2 93.92(11) . . ?
O4 Mn1 N2 86.79(10) . . ?
N1 Mn1 N2 84.86(10) . . ?
N4 Mn1 N2 162.28(10) . . ?
N3 Mn1 N2 79.28(11) . . ?
O5 N5 O6 119.5(4) . . ?
O5 N5 O7 120.5(4) . . ?
O6 N5 O7 120.0(4) . . ?

_diffrn_measured_fraction_theta_max 0.947
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.947
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.061
