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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_P21C
_database_code_depnum_ccdc_archive 'CCDC 1544526'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2017-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H34 Mn N5 O6'
_chemical_formula_weight         543.50

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   8.0291(5)
_cell_length_b                   19.2541(12)
_cell_length_c                   16.7664(11)
_cell_angle_alpha                90
_cell_angle_beta                 101.6530(10)
_cell_angle_gamma                90
_cell_volume                     2538.5(3)
_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_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_F_000             1144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.569
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30033
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.798
_diffrn_reflns_theta_max         37.519
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             11528
_reflns_number_gt                10053
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0131P)²+2.2318P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11528
_refine_ls_number_parameters     338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1060
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   1.211
_refine_ls_restrained_S_all      1.211
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.82901(11) 0.15092(4) 0.44281(5) 0.01533(15) Uani 1 1 d . . . . .
C1 C 0.72079(14) 0.15943(6) 0.37234(7) 0.01578(19) Uani 1 1 d . . . . .
C2 C 0.65255(17) 0.10021(8) 0.32770(9) 0.0240(2) Uani 1 1 d . . . . .
H1 H 0.6854 0.0552 0.3484 0.029 Uiso 1 1 calc R U . . .
C3 C 0.53781(18) 0.10684(9) 0.25386(9) 0.0288(3) Uani 1 1 d . . . . .
H2 H 0.4937 0.0663 0.2247 0.035 Uiso 1 1 calc R U . . .
C4 C 0.48659(18) 0.17227(10) 0.22196(9) 0.0291(3) Uani 1 1 d . . . . .
H3 H 0.4098 0.1764 0.1710 0.035 Uiso 1 1 calc R U . . .
C5 C 0.54888(17) 0.23061(9) 0.26529(8) 0.0252(3) Uani 1 1 d . . . . .
H4 H 0.5125 0.2752 0.2444 0.030 Uiso 1 1 calc R U . . .
C6 C 0.66602(15) 0.22554(7) 0.34032(7) 0.0175(2) Uani 1 1 d . . . . .
C7 C 0.70573(16) 0.28777(7) 0.38792(8) 0.0193(2) Uani 1 1 d . . . . .
H5 H 0.6411 0.3282 0.3703 0.023 Uiso 1 1 calc R U . . .
N1 N 0.82277(13) 0.29252(5) 0.45284(7) 0.01649(17) Uani 1 1 d . . . . .
C8 C 0.81372(16) 0.35303(6) 0.50599(9) 0.0201(2) Uani 1 1 d . . . . .
H6 H 0.7329 0.3876 0.4765 0.024 Uiso 1 1 calc R U . . .
H7 H 0.9270 0.3752 0.5208 0.024 Uiso 1 1 calc R U . . .
C9 C 0.75538(17) 0.32990(7) 0.58308(10) 0.0247(3) Uani 1 1 d . . . . .
H8 H 0.7306 0.3717 0.6131 0.030 Uiso 1 1 calc R U . . .
H9 H 0.6480 0.3035 0.5671 0.030 Uiso 1 1 calc R U . . .
C10 C 0.88342(18) 0.28518(7) 0.64021(9) 0.0227(2) Uani 1 1 d . . . . .
H10 H 0.9936 0.3099 0.6533 0.027 Uiso 1 1 calc R U . . .
H11 H 0.8432 0.2782 0.6917 0.027 Uiso 1 1 calc R U . . .
N2 N 0.90919(13) 0.21665(6) 0.60464(7) 0.01802(18) Uani 1 1 d . . . . .
H12 H 0.813(3) 0.1939(11) 0.5972(13) 0.027(5) Uiso 1 1 d . . . . .
C11 C 1.03368(16) 0.17403(7) 0.66117(8) 0.0205(2) Uani 1 1 d . . . . .
H13 H 0.9867 0.1610 0.7093 0.025 Uiso 1 1 calc R U . . .
H14 H 1.1398 0.2006 0.6800 0.025 Uiso 1 1 calc R U . . .
C12 C 1.06999(16) 0.10948(7) 0.61598(8) 0.0202(2) Uani 1 1 d . . . . .
H15 H 1.1513 0.0792 0.6525 0.024 Uiso 1 1 calc R U . . .
H16 H 0.9636 0.0831 0.5968 0.024 Uiso 1 1 calc R U . . .
N3 N 1.14333(13) 0.13158(6) 0.54558(7) 0.01671(17) Uani 1 1 d . . . . .
H17 H 1.246(2) 0.1485(10) 0.5680(12) 0.019(4) Uiso 1 1 d . . . . .
C13 C 1.16377(17) 0.07132(7) 0.49310(9) 0.0220(2) Uani 1 1 d . . . . .
H18 H 1.0506 0.0507 0.4718 0.026 Uiso 1 1 calc R U . . .
H19 H 1.2344 0.0357 0.5266 0.026 Uiso 1 1 calc R U . . .
C14 C 1.24590(18) 0.09045(8) 0.42171(9) 0.0244(2) Uani 1 1 d . . . . .
H20 H 1.2706 0.0473 0.3942 0.029 Uiso 1 1 calc R U . . .
H21 H 1.3556 0.1139 0.4430 0.029 Uiso 1 1 calc R U . . .
C15 C 1.1366(2) 0.13774(7) 0.35909(8) 0.0240(3) Uani 1 1 d . . . . .
H22 H 1.1893 0.1427 0.3109 0.029 Uiso 1 1 calc R U . . .
H23 H 1.0223 0.1171 0.3411 0.029 Uiso 1 1 calc R U . . .
N4 N 1.12138(16) 0.20643(6) 0.39553(7) 0.0204(2) Uani 1 1 d . . . . .
C16 C 1.20978(18) 0.25597(7) 0.37305(7) 0.0203(2) Uani 1 1 d . . . . .
H24 H 1.2598 0.2480 0.3271 0.024 Uiso 1 1 calc R U . . .
C17 C 1.23803(14) 0.32268(6) 0.41279(7) 0.01543(18) Uani 1 1 d . . . . .
C18 C 1.30478(16) 0.37704(7) 0.37238(8) 0.0191(2) Uani 1 1 d . . . . .
H25 H 1.3227 0.3698 0.3187 0.023 Uiso 1 1 calc R U . . .
C19 C 1.34446(16) 0.44051(7) 0.40957(9) 0.0209(2) Uani 1 1 d . . . . .
H26 H 1.3880 0.4771 0.3817 0.025 Uiso 1 1 calc R U . . .
C20 C 1.31958(15) 0.45023(6) 0.48902(9) 0.0199(2) Uani 1 1 d . . . . .
H27 H 1.3459 0.4939 0.5149 0.024 Uiso 1 1 calc R U . . .
C21 C 1.25716(14) 0.39726(6) 0.53054(8) 0.01649(19) Uani 1 1 d . . . . .
H28 H 1.2426 0.4050 0.5847 0.020 Uiso 1 1 calc R U . . .
C22 C 1.21478(13) 0.33201(6) 0.49367(7) 0.01266(17) Uani 1 1 d . . . . .
O2 O 1.15853(10) 0.28229(4) 0.53636(5) 0.01298(13) Uani 1 1 d . . . . .
Mn1 Mn 0.99374(2) 0.21617(2) 0.49043(2) 0.01076(4) Uani 1 1 d . . . . .
N5 N 0.56472(14) 0.38255(6) 0.15350(7) 0.0206(2) Uani 1 1 d . . . . .
O4 O 0.52688(15) 0.34090(6) 0.09576(7) 0.0294(2) Uani 1 1 d . . . . .
O3 O 0.71287(15) 0.40367(10) 0.17476(11) 0.0532(5) Uani 1 1 d . . . . .
O5 O 0.45561(15) 0.40258(8) 0.19218(8) 0.0357(3) Uani 1 1 d . . . . .
C23 C 0.9562(2) 0.51616(8) 0.29613(10) 0.0274(3) Uani 1 1 d . . . . .
H29 H 0.9139 0.5035 0.2390 0.041 Uiso 1 1 calc R U . . .
H30 H 1.0809 0.5160 0.3078 0.041 Uiso 1 1 calc R U . . .
H31 H 0.9152 0.5627 0.3062 0.041 Uiso 1 1 calc R U . . .
C24 C 0.89259(18) 0.46431(8) 0.35067(9) 0.0247(3) Uani 1 1 d . . . . .
H32 H 0.9324 0.4173 0.3395 0.030 Uiso 1 1 calc R U . . .
H33 H 0.9416 0.4757 0.4082 0.030 Uiso 1 1 calc R U . . .
O6 O 0.71163(13) 0.46384(6) 0.33909(7) 0.02451(19) Uani 1 1 d . . . . .
H34 H 0.673(3) 0.4500(14) 0.2908(17) 0.049(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
O1 C1 1.3279(14) . ?
O1 Mn1 1.8811(8) . ?
C1 C2 1.4124(18) . ?
C1 C6 1.4165(18) . ?
C2 C3 1.392(2) . ?
C2 H1 0.9500 . ?
C3 C4 1.398(3) . ?
C3 H2 0.9500 . ?
C4 C5 1.376(2) . ?
C4 H3 0.9500 . ?
C5 C6 1.4137(17) . ?
C5 H4 0.9500 . ?
C6 C7 1.4393(19) . ?
C7 N1 1.2896(16) . ?
C7 H5 0.9500 . ?
N1 C8 1.4775(17) . ?
N1 Mn1 2.0231(10) . ?
C8 C9 1.527(2) . ?
C8 H6 0.9900 . ?
C8 H7 0.9900 . ?
C9 C10 1.522(2) . ?
C9 H8 0.9900 . ?
C9 H9 0.9900 . ?
C10 N2 1.4795(17) . ?
C10 H10 0.9900 . ?
C10 H11 0.9900 . ?
N2 C11 1.4792(17) . ?
N2 Mn1 2.1570(11) . ?
N2 H12 0.87(2) . ?
C11 C12 1.514(2) . ?
C11 H13 0.9900 . ?
C11 H14 0.9900 . ?
C12 N3 1.4838(16) . ?
C12 H15 0.9900 . ?
C12 H16 0.9900 . ?
N3 C13 1.4851(17) . ?
N3 Mn1 2.1217(11) . ?
N3 H17 0.90(2) . ?
C13 C14 1.524(2) . ?
C13 H18 0.9900 . ?
C13 H19 0.9900 . ?
C14 C15 1.526(2) . ?
C14 H20 0.9900 . ?
C14 H21 0.9900 . ?
C15 N4 1.4723(18) . ?
C15 H22 0.9900 . ?
C15 H23 0.9900 . ?
N4 C16 1.2898(16) . ?
N4 Mn1 2.0679(12) . ?
C16 C17 1.4437(18) . ?
C16 H24 0.9500 . ?
C17 C18 1.4101(16) . ?
C17 C22 1.4171(16) . ?
C18 C19 1.3797(19) . ?
C18 H25 0.9500 . ?
C19 C20 1.399(2) . ?
C19 H26 0.9500 . ?
C20 C21 1.3846(17) . ?
C20 H27 0.9500 . ?
C21 C22 1.4110(16) . ?
C21 H28 0.9500 . ?
C22 O2 1.3280(13) . ?
O2 Mn1 1.8849(8) . ?
N5 O3 1.2394(16) . ?
N5 O4 1.2465(16) . ?
N5 O5 1.2516(16) . ?
C23 C24 1.511(2) . ?
C23 H29 0.9800 . ?
C23 H30 0.9800 . ?
C23 H31 0.9800 . ?
C24 O6 1.4265(17) . ?
C24 H32 0.9900 . ?
C24 H33 0.9900 . ?
O6 H34 0.85(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 Mn1 124.96(8) . . ?
O1 C1 C2 119.08(12) . . ?
O1 C1 C6 123.05(10) . . ?
C2 C1 C6 117.84(11) . . ?
C3 C2 C1 120.90(14) . . ?
C3 C2 H1 119.5 . . ?
C1 C2 H1 119.5 . . ?
C2 C3 C4 120.92(13) . . ?
C2 C3 H2 119.5 . . ?
C4 C3 H2 119.5 . . ?
C5 C4 C3 119.11(13) . . ?
C5 C4 H3 120.4 . . ?
C3 C4 H3 120.4 . . ?
C4 C5 C6 121.26(15) . . ?
C4 C5 H4 119.4 . . ?
C6 C5 H4 119.4 . . ?
C5 C6 C1 119.95(12) . . ?
C5 C6 C7 117.97(12) . . ?
C1 C6 C7 121.39(11) . . ?
N1 C7 C6 124.69(12) . . ?
N1 C7 H5 117.7 . . ?
C6 C7 H5 117.7 . . ?
C7 N1 C8 116.67(11) . . ?
C7 N1 Mn1 122.98(9) . . ?
C8 N1 Mn1 119.87(8) . . ?
N1 C8 C9 109.96(10) . . ?
N1 C8 H6 109.7 . . ?
C9 C8 H6 109.7 . . ?
N1 C8 H7 109.7 . . ?
C9 C8 H7 109.7 . . ?
H6 C8 H7 108.2 . . ?
C10 C9 C8 114.44(10) . . ?
C10 C9 H8 108.7 . . ?
C8 C9 H8 108.7 . . ?
C10 C9 H9 108.7 . . ?
C8 C9 H9 108.7 . . ?
H8 C9 H9 107.6 . . ?
N2 C10 C9 112.49(12) . . ?
N2 C10 H10 109.1 . . ?
C9 C10 H10 109.1 . . ?
N2 C10 H11 109.1 . . ?
C9 C10 H11 109.1 . . ?
H10 C10 H11 107.8 . . ?
C11 N2 C10 111.59(11) . . ?
C11 N2 Mn1 105.86(8) . . ?
C10 N2 Mn1 117.15(8) . . ?
C11 N2 H12 106.0(14) . . ?
C10 N2 H12 108.3(14) . . ?
Mn1 N2 H12 107.3(14) . . ?
N2 C11 C12 107.95(10) . . ?
N2 C11 H13 110.1 . . ?
C12 C11 H13 110.1 . . ?
N2 C11 H14 110.1 . . ?
C12 C11 H14 110.1 . . ?
H13 C11 H14 108.4 . . ?
N3 C12 C11 108.06(10) . . ?
N3 C12 H15 110.1 . . ?
C11 C12 H15 110.1 . . ?
N3 C12 H16 110.1 . . ?
C11 C12 H16 110.1 . . ?
H15 C12 H16 108.4 . . ?
C12 N3 C13 110.88(10) . . ?
C12 N3 Mn1 106.63(8) . . ?
C13 N3 Mn1 117.52(8) . . ?
C12 N3 H17 104.5(12) . . ?
C13 N3 H17 109.2(12) . . ?
Mn1 N3 H17 107.3(12) . . ?
N3 C13 C14 113.19(11) . . ?
N3 C13 H18 108.9 . . ?
C14 C13 H18 108.9 . . ?
N3 C13 H19 108.9 . . ?
C14 C13 H19 108.9 . . ?
H18 C13 H19 107.8 . . ?
C13 C14 C15 113.88(11) . . ?
C13 C14 H20 108.8 . . ?
C15 C14 H20 108.8 . . ?
C13 C14 H21 108.8 . . ?
C15 C14 H21 108.8 . . ?
H20 C14 H21 107.7 . . ?
N4 C15 C14 109.57(11) . . ?
N4 C15 H22 109.8 . . ?
C14 C15 H22 109.8 . . ?
N4 C15 H23 109.8 . . ?
C14 C15 H23 109.8 . . ?
H22 C15 H23 108.2 . . ?
C16 N4 C15 116.50(12) . . ?
C16 N4 Mn1 123.05(9) . . ?
C15 N4 Mn1 119.76(8) . . ?
N4 C16 C17 124.58(12) . . ?
N4 C16 H24 117.7 . . ?
C17 C16 H24 117.7 . . ?
C18 C17 C22 120.13(11) . . ?
C18 C17 C16 118.56(11) . . ?
C22 C17 C16 121.04(10) . . ?
C19 C18 C17 121.04(12) . . ?
C19 C18 H25 119.5 . . ?
C17 C18 H25 119.5 . . ?
C18 C19 C20 118.98(11) . . ?
C18 C19 H26 120.5 . . ?
C20 C19 H26 120.5 . . ?
C21 C20 C19 121.07(12) . . ?
C21 C20 H27 119.5 . . ?
C19 C20 H27 119.5 . . ?
C20 C21 C22 121.02(12) . . ?
C20 C21 H28 119.5 . . ?
C22 C21 H28 119.5 . . ?
O2 C22 C21 118.94(10) . . ?
O2 C22 C17 123.31(10) . . ?
C21 C22 C17 117.73(10) . . ?
C22 O2 Mn1 123.63(7) . . ?
O1 Mn1 O2 179.00(4) . . ?
O1 Mn1 N1 88.76(4) . . ?
O2 Mn1 N1 90.72(4) . . ?
O1 Mn1 N4 91.61(4) . . ?
O2 Mn1 N4 87.68(4) . . ?
N1 Mn1 N4 103.69(5) . . ?
O1 Mn1 N3 87.70(4) . . ?
O2 Mn1 N3 92.96(4) . . ?
N1 Mn1 N3 169.20(4) . . ?
N4 Mn1 N3 86.61(4) . . ?
O1 Mn1 N2 93.40(4) . . ?
O2 Mn1 N2 87.43(4) . . ?
N1 Mn1 N2 87.59(4) . . ?
N4 Mn1 N2 167.75(5) . . ?
N3 Mn1 N2 82.44(4) . . ?
O3 N5 O4 120.24(13) . . ?
O3 N5 O5 118.78(13) . . ?
O4 N5 O5 120.95(12) . . ?
C24 C23 H29 109.5 . . ?
C24 C23 H30 109.5 . . ?
H29 C23 H30 109.5 . . ?
C24 C23 H31 109.5 . . ?
H29 C23 H31 109.5 . . ?
H30 C23 H31 109.5 . . ?
O6 C24 C23 112.42(12) . . ?
O6 C24 H32 109.1 . . ?
C23 C24 H32 109.1 . . ?
O6 C24 H33 109.1 . . ?
C23 C24 H33 109.1 . . ?
H32 C24 H33 107.9 . . ?
C24 O6 H34 107.2(18) . . ?

_refine_diff_density_max         0.648
_refine_diff_density_min         -0.890
_refine_diff_density_rms         0.081

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1544519'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2017-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H28 As F6 Mn N4 O2'
_chemical_formula_weight         624.34

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
As As 0.0499 2.0058 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   8.2840(7)
_cell_length_b                   17.2411(15)
_cell_length_c                   17.8357(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2547.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    164(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_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    1.878
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.720
_exptl_absorpt_correction_T_max  0.813
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      164(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31842
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.284
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4704
_reflns_number_gt                4502
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.994

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²+7.0690P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1865 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_chemical_absolute_configuration .
_refine_ls_number_reflns         4704
_refine_ls_number_parameters     333
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1105
_refine_ls_wR_factor_gt          0.1084
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9975(6) 0.4638(3) 0.3978(2) 0.0328(11) Uani 1 1 d . . . . .
C1 C 1.0684(9) 0.4001(4) 0.4237(4) 0.0330(16) Uani 1 1 d . . . . .
C2 C 1.1390(12) 0.3490(5) 0.3738(4) 0.051(2) Uani 1 1 d . . . . .
H1 H 1.1343 0.3599 0.3217 0.062 Uiso 1 1 calc R U . . .
C3 C 1.2166(12) 0.2822(6) 0.3980(5) 0.054(2) Uani 1 1 d . . . . .
H2 H 1.2625 0.2478 0.3623 0.065 Uiso 1 1 calc R U . . .
C4 C 1.2278(10) 0.2651(4) 0.4744(5) 0.0418(19) Uani 1 1 d . . . . .
H3 H 1.2784 0.2187 0.4911 0.050 Uiso 1 1 calc R U . . .
C5 C 1.1641(9) 0.3167(4) 0.5247(4) 0.0347(15) Uani 1 1 d . . . . .
H4 H 1.1743 0.3065 0.5768 0.042 Uiso 1 1 calc R U . . .
C6 C 1.0842(8) 0.3843(4) 0.5013(4) 0.0279(14) Uani 1 1 d . . . . .
C7 C 1.0423(8) 0.4425(4) 0.5565(4) 0.0283(14) Uani 1 1 d . . . . .
H5 H 1.0805 0.4350 0.6062 0.034 Uiso 1 1 calc R U . . .
N1 N 0.9573(7) 0.5036(3) 0.5437(3) 0.0256(12) Uani 1 1 d . . . . .
C8 C 0.9694(9) 0.5673(4) 0.5988(4) 0.0293(15) Uani 1 1 d . . . . .
H6 H 1.0198 0.5479 0.6455 0.035 Uiso 1 1 calc R U . . .
H7 H 0.8600 0.5866 0.6112 0.035 Uiso 1 1 calc R U . . .
C9 C 1.0699(9) 0.6326(4) 0.5667(4) 0.0336(16) Uani 1 1 d . . . . .
H8 H 1.1735 0.6109 0.5487 0.040 Uiso 1 1 calc R U . . .
H9 H 1.0947 0.6698 0.6074 0.040 Uiso 1 1 calc R U . . .
C10 C 0.9902(9) 0.6765(4) 0.5024(4) 0.0331(15) Uani 1 1 d . . . . .
H10 H 0.8831 0.6954 0.5188 0.040 Uiso 1 1 calc R U . . .
H11 H 1.0570 0.7222 0.4894 0.040 Uiso 1 1 calc R U . . .
N2 N 0.9701(7) 0.6272(3) 0.4348(3) 0.0252(12) Uani 1 1 d D . . . .
H12 H 1.064(7) 0.617(4) 0.426(4) 0.013(16) Uiso 1 1 d D . . . .
C11 C 0.8927(8) 0.6705(4) 0.3722(4) 0.0289(15) Uani 1 1 d . . . . .
H13 H 0.9670 0.7109 0.3532 0.035 Uiso 1 1 calc R U . . .
H14 H 0.7929 0.6961 0.3901 0.035 Uiso 1 1 calc R U . . .
C12 C 0.8527(9) 0.6137(4) 0.3103(4) 0.0284(14) Uani 1 1 d . . . . .
H15 H 0.7959 0.6408 0.2691 0.034 Uiso 1 1 calc R U . . .
H16 H 0.9533 0.5910 0.2899 0.034 Uiso 1 1 calc R U . . .
N3 N 0.7495(7) 0.5520(3) 0.3409(3) 0.0254(12) Uani 1 1 d . . . . .
H17 H 0.657(10) 0.573(4) 0.350(4) 0.024(18) Uiso 1 1 d . . . . .
C13 C 0.7275(9) 0.4884(4) 0.2865(4) 0.0310(15) Uani 1 1 d . . . . .
H18 H 0.8335 0.4640 0.2766 0.037 Uiso 1 1 calc R U . . .
H19 H 0.6878 0.5104 0.2387 0.037 Uiso 1 1 calc R U . . .
C14 C 0.6100(11) 0.4264(4) 0.3130(4) 0.0406(19) Uani 1 1 d . . . . .
H20 H 0.5905 0.3897 0.2713 0.049 Uiso 1 1 calc R U . . .
H21 H 0.5058 0.4514 0.3254 0.049 Uiso 1 1 calc R U . . .
C15 C 0.6685(12) 0.3809(4) 0.3813(4) 0.0424(19) Uani 1 1 d . . . . .
H22 H 0.5931 0.3376 0.3917 0.051 Uiso 1 1 calc R U . . .
H23 H 0.7763 0.3586 0.3709 0.051 Uiso 1 1 calc R U . . .
N4 N 0.6778(8) 0.4325(3) 0.4475(3) 0.0352(14) Uani 1 1 d . . . . .
C16 C 0.5704(10) 0.4243(4) 0.4986(4) 0.0373(17) Uani 1 1 d . . . . .
H24 H 0.5072 0.3783 0.4975 0.045 Uiso 1 1 calc R U . . .
C17 C 0.5376(8) 0.4797(4) 0.5579(4) 0.0294(14) Uani 1 1 d . . . . .
C18 C 0.4426(9) 0.4582(5) 0.6191(4) 0.0384(17) Uani 1 1 d . . . . .
H25 H 0.4119 0.4054 0.6248 0.046 Uiso 1 1 calc R U . . .
C19 C 0.3924(9) 0.5118(5) 0.6715(4) 0.0386(18) Uani 1 1 d . . . . .
H26 H 0.3293 0.4963 0.7134 0.046 Uiso 1 1 calc R U . . .
C20 C 0.4358(9) 0.5882(5) 0.6618(4) 0.0375(17) Uani 1 1 d . . . . .
H27 H 0.3989 0.6260 0.6965 0.045 Uiso 1 1 calc R U . . .
C21 C 0.5320(8) 0.6106(4) 0.6027(4) 0.0297(15) Uani 1 1 d . . . . .
H28 H 0.5617 0.6636 0.5980 0.036 Uiso 1 1 calc R U . . .
C22 C 0.5868(7) 0.5575(4) 0.5494(4) 0.0256(13) Uani 1 1 d . . . . .
O2 O 0.6804(5) 0.5820(2) 0.4941(2) 0.0229(9) Uani 1 1 d . . . . .
Mn1 Mn 0.83935(11) 0.52203(5) 0.44699(5) 0.0218(2) Uani 1 1 d . . . . .
As1 As 0.36730(8) 0.68775(4) 0.28387(4) 0.02999(19) Uani 1 1 d . . . . .
F1 F 0.5072(8) 0.6807(4) 0.3530(4) 0.090(3) Uani 1 1 d . . . . .
F2 F 0.2771(8) 0.7621(4) 0.3287(4) 0.088(3) Uani 1 1 d . . . . .
F3 F 0.4884(14) 0.7493(5) 0.2392(7) 0.165(6) Uani 1 1 d . . . . .
F4 F 0.2260(10) 0.6920(6) 0.2165(4) 0.128(4) Uani 1 1 d . . . . .
F5 F 0.4602(8) 0.6124(4) 0.2388(3) 0.0684(17) Uani 1 1 d . . . . .
F6 F 0.2498(10) 0.6239(6) 0.3276(6) 0.123(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
O1 C1 1.328(8) . ?
O1 Mn1 1.870(5) . ?
C1 C2 1.382(10) . ?
C1 C6 1.416(10) . ?
C2 C3 1.388(12) . ?
C2 H1 0.9500 . ?
C3 C4 1.398(13) . ?
C3 H2 0.9500 . ?
C4 C5 1.369(11) . ?
C4 H3 0.9500 . ?
C5 C6 1.404(10) . ?
C5 H4 0.9500 . ?
C6 C7 1.449(9) . ?
C7 N1 1.287(8) . ?
C7 H5 0.9500 . ?
N1 C8 1.477(8) . ?
N1 Mn1 2.007(5) . ?
C8 C9 1.513(10) . ?
C8 H6 0.9900 . ?
C8 H7 0.9900 . ?
C9 C10 1.525(10) . ?
C9 H8 0.9900 . ?
C9 H9 0.9900 . ?
C10 N2 1.484(8) . ?
C10 H10 0.9900 . ?
C10 H11 0.9900 . ?
N2 C11 1.488(8) . ?
N2 Mn1 2.123(6) . ?
N2 H12 0.81(5) . ?
C11 C12 1.512(9) . ?
C11 H13 0.9900 . ?
C11 H14 0.9900 . ?
C12 N3 1.470(9) . ?
C12 H15 0.9900 . ?
C12 H16 0.9900 . ?
N3 C13 1.476(9) . ?
N3 Mn1 2.097(6) . ?
N3 H17 0.86(8) . ?
C13 C14 1.521(10) . ?
C13 H18 0.9900 . ?
C13 H19 0.9900 . ?
C14 C15 1.528(10) . ?
C14 H20 0.9900 . ?
C14 H21 0.9900 . ?
C15 N4 1.481(9) . ?
C15 H22 0.9900 . ?
C15 H23 0.9900 . ?
N4 C16 1.281(10) . ?
N4 Mn1 2.043(6) . ?
C16 C17 1.452(10) . ?
C16 H24 0.9500 . ?
C17 C18 1.396(10) . ?
C17 C22 1.410(9) . ?
C18 C19 1.379(11) . ?
C18 H25 0.9500 . ?
C19 C20 1.376(12) . ?
C19 H26 0.9500 . ?
C20 C21 1.377(10) . ?
C20 H27 0.9500 . ?
C21 C22 1.394(10) . ?
C21 H28 0.9500 . ?
C22 O2 1.323(8) . ?
O2 Mn1 1.873(4) . ?
As1 F3 1.663(8) . ?
As1 F6 1.664(7) . ?
As1 F4 1.679(6) . ?
As1 F2 1.685(5) . ?
As1 F1 1.697(5) . ?
As1 F5 1.710(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
C1 O1 Mn1 126.2(4) . . ?
O1 C1 C2 119.3(7) . . ?
O1 C1 C6 122.7(6) . . ?
C2 C1 C6 117.9(7) . . ?
C1 C2 C3 121.7(7) . . ?
C1 C2 H1 119.2 . . ?
C3 C2 H1 119.2 . . ?
C2 C3 C4 120.6(8) . . ?
C2 C3 H2 119.7 . . ?
C4 C3 H2 119.7 . . ?
C5 C4 C3 118.4(7) . . ?
C5 C4 H3 120.8 . . ?
C3 C4 H3 120.8 . . ?
C4 C5 C6 121.8(7) . . ?
C4 C5 H4 119.1 . . ?
C6 C5 H4 119.1 . . ?
C5 C6 C1 119.6(6) . . ?
C5 C6 C7 119.1(6) . . ?
C1 C6 C7 120.6(6) . . ?
N1 C7 C6 125.2(6) . . ?
N1 C7 H5 117.4 . . ?
C6 C7 H5 117.4 . . ?
C7 N1 C8 116.9(6) . . ?
C7 N1 Mn1 123.3(5) . . ?
C8 N1 Mn1 119.1(4) . . ?
N1 C8 C9 109.8(5) . . ?
N1 C8 H6 109.7 . . ?
C9 C8 H6 109.7 . . ?
N1 C8 H7 109.7 . . ?
C9 C8 H7 109.7 . . ?
H6 C8 H7 108.2 . . ?
C8 C9 C10 114.6(6) . . ?
C8 C9 H8 108.6 . . ?
C10 C9 H8 108.6 . . ?
C8 C9 H9 108.6 . . ?
C10 C9 H9 108.6 . . ?
H8 C9 H9 107.6 . . ?
N2 C10 C9 112.0(6) . . ?
N2 C10 H10 109.2 . . ?
C9 C10 H10 109.2 . . ?
N2 C10 H11 109.2 . . ?
C9 C10 H11 109.2 . . ?
H10 C10 H11 107.9 . . ?
C10 N2 C11 111.7(5) . . ?
C10 N2 Mn1 117.6(4) . . ?
C11 N2 Mn1 106.6(4) . . ?
C10 N2 H12 101(5) . . ?
C11 N2 H12 112(5) . . ?
Mn1 N2 H12 108(5) . . ?
N2 C11 C12 108.5(5) . . ?
N2 C11 H13 110.0 . . ?
C12 C11 H13 110.0 . . ?
N2 C11 H14 110.0 . . ?
C12 C11 H14 110.0 . . ?
H13 C11 H14 108.4 . . ?
N3 C12 C11 108.9(5) . . ?
N3 C12 H15 109.9 . . ?
C11 C12 H15 109.9 . . ?
N3 C12 H16 109.9 . . ?
C11 C12 H16 109.9 . . ?
H15 C12 H16 108.3 . . ?
C12 N3 C13 111.4(5) . . ?
C12 N3 Mn1 107.9(4) . . ?
C13 N3 Mn1 117.0(4) . . ?
C12 N3 H17 106(5) . . ?
C13 N3 H17 109(5) . . ?
Mn1 N3 H17 105(5) . . ?
N3 C13 C14 113.4(6) . . ?
N3 C13 H18 108.9 . . ?
C14 C13 H18 108.9 . . ?
N3 C13 H19 108.9 . . ?
C14 C13 H19 108.9 . . ?
H18 C13 H19 107.7 . . ?
C13 C14 C15 113.9(7) . . ?
C13 C14 H20 108.8 . . ?
C15 C14 H20 108.8 . . ?
C13 C14 H21 108.8 . . ?
C15 C14 H21 108.8 . . ?
H20 C14 H21 107.7 . . ?
N4 C15 C14 110.1(6) . . ?
N4 C15 H22 109.6 . . ?
C14 C15 H22 109.6 . . ?
N4 C15 H23 109.6 . . ?
C14 C15 H23 109.6 . . ?
H22 C15 H23 108.2 . . ?
C16 N4 C15 117.6(7) . . ?
C16 N4 Mn1 122.8(5) . . ?
C15 N4 Mn1 119.0(5) . . ?
N4 C16 C17 125.1(7) . . ?
N4 C16 H24 117.5 . . ?
C17 C16 H24 117.5 . . ?
C18 C17 C22 119.9(7) . . ?
C18 C17 C16 120.0(7) . . ?
C22 C17 C16 119.7(6) . . ?
C19 C18 C17 121.5(7) . . ?
C19 C18 H25 119.3 . . ?
C17 C18 H25 119.3 . . ?
C20 C19 C18 118.5(7) . . ?
C20 C19 H26 120.7 . . ?
C18 C19 H26 120.7 . . ?
C19 C20 C21 121.1(7) . . ?
C19 C20 H27 119.5 . . ?
C21 C20 H27 119.5 . . ?
C20 C21 C22 121.7(7) . . ?
C20 C21 H28 119.1 . . ?
C22 C21 H28 119.1 . . ?
O2 C22 C21 119.3(6) . . ?
O2 C22 C17 123.5(6) . . ?
C21 C22 C17 117.2(6) . . ?
C22 O2 Mn1 124.8(4) . . ?
O1 Mn1 O2 178.6(2) . . ?
O1 Mn1 N1 88.7(2) . . ?
O2 Mn1 N1 92.5(2) . . ?
O1 Mn1 N4 93.2(2) . . ?
O2 Mn1 N4 87.4(2) . . ?
N1 Mn1 N4 101.3(2) . . ?
O1 Mn1 N3 87.6(2) . . ?
O2 Mn1 N3 91.1(2) . . ?
N1 Mn1 N3 170.5(2) . . ?
N4 Mn1 N3 87.6(2) . . ?
O1 Mn1 N2 93.1(2) . . ?
O2 Mn1 N2 86.2(2) . . ?
N1 Mn1 N2 88.6(2) . . ?
N4 Mn1 N2 168.5(2) . . ?
N3 Mn1 N2 83.0(2) . . ?
F3 As1 F6 178.2(5) . . ?
F3 As1 F4 92.9(6) . . ?
F6 As1 F4 87.5(6) . . ?
F3 As1 F2 90.6(5) . . ?
F6 As1 F2 91.2(5) . . ?
F4 As1 F2 89.9(3) . . ?
F3 As1 F1 89.0(6) . . ?
F6 As1 F1 90.7(5) . . ?
F4 As1 F1 178.1(5) . . ?
F2 As1 F1 90.7(3) . . ?
F3 As1 F5 89.3(4) . . ?
F6 As1 F5 88.9(4) . . ?
F4 As1 F5 90.6(3) . . ?
F2 As1 F5 179.5(3) . . ?
F1 As1 F5 88.8(3) . . ?

_refine_diff_density_max         0.963
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.088

####################################################################### 
# 
# 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_P
_database_code_depnum_ccdc_archive 'CCDC 1544521'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2017-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H28 As F6 Mn N4 O2'
_chemical_formula_weight         624.34

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
As As 0.0499 2.0058 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   8.2287(11)
_cell_length_b                   17.549(2)
_cell_length_c                   18.186(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2626.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(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_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    1.822
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.718
_exptl_absorpt_correction_T_max  0.812
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22182
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.321
_diffrn_reflns_theta_max         28.547
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             6524
_reflns_number_gt                4582
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_max     0.971
_reflns_Friedel_fraction_full    0.991

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1201P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1544 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_chemical_absolute_configuration .
_refine_ls_number_reflns         6524
_refine_ls_number_parameters     333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.1817
_refine_ls_wR_factor_gt          0.1666
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.29403(13) 0.98024(5) 0.05146(5) 0.0437(3) Uani 1 1 d . . . . .
O1 O 0.1428(6) 0.9201(2) 0.0008(3) 0.0499(11) Uani 1 1 d . . . . .
C1 C 0.0585(8) 0.9451(4) -0.0567(4) 0.0458(14) Uani 1 1 d . . . . .
C2 C 0.0152(11) 0.8926(5) -0.1111(4) 0.0591(18) Uani 1 1 d . . . . .
H1 H 0.0447 0.8417 -0.1059 0.071 Uiso 1 1 calc R U . . .
C3 C -0.0716(12) 0.9156(7) -0.1730(5) 0.076(3) Uani 1 1 d . . . . .
H2 H -0.1009 0.8800 -0.2085 0.091 Uiso 1 1 calc R U . . .
C4 C -0.1145(12) 0.9914(6) -0.1818(5) 0.076(3) Uani 1 1 d . . . . .
H3 H -0.1678 1.0070 -0.2243 0.091 Uiso 1 1 calc R U . . .
C5 C -0.0787(11) 1.0434(6) -0.1282(5) 0.067(2) Uani 1 1 d . . . . .
H4 H -0.1100 1.0939 -0.1340 0.081 Uiso 1 1 calc R U . . .
C6 C 0.0045(9) 1.0213(4) -0.0648(4) 0.0503(15) Uani 1 1 d . . . . .
C7 C 0.0179(11) 1.0751(4) -0.0036(5) 0.0575(18) Uani 1 1 d . . . . .
H5 H -0.0489 1.1178 -0.0038 0.069 Uiso 1 1 calc R U . . .
N1 N 0.1163(8) 1.0665(3) 0.0503(3) 0.0536(14) Uani 1 1 d . . . . .
C8 C 0.0931(13) 1.1157(4) 0.1158(5) 0.066(2) Uani 1 1 d . . . . .
H6 H 0.0134 1.1549 0.1051 0.079 Uiso 1 1 calc R U . . .
H7 H 0.1948 1.1404 0.1284 0.079 Uiso 1 1 calc R U . . .
C9 C 0.0350(15) 1.0668(5) 0.1801(5) 0.079(3) Uani 1 1 d . . . . .
H8 H 0.0020 1.1004 0.2197 0.095 Uiso 1 1 calc R U . . .
H9 H -0.0604 1.0386 0.1645 0.095 Uiso 1 1 calc R U . . .
C10 C 0.1581(13) 1.0107(5) 0.2099(4) 0.071(2) Uani 1 1 d . . . . .
H10 H 0.2585 1.0375 0.2207 0.086 Uiso 1 1 calc R U . . .
H11 H 0.1175 0.9893 0.2555 0.086 Uiso 1 1 calc R U . . .
N2 N 0.1918(10) 0.9485(3) 0.1577(3) 0.0568(15) Uani 1 1 d . . . . .
H12 H 0.090(13) 0.933(5) 0.155(5) 0.06(3) Uiso 1 1 d . . . . .
C11 C 0.3008(12) 0.8901(5) 0.1899(4) 0.0637(19) Uani 1 1 d . . . . .
H13 H 0.2463 0.8642 0.2301 0.076 Uiso 1 1 calc R U . . .
H14 H 0.3982 0.9141 0.2091 0.076 Uiso 1 1 calc R U . . .
C12 C 0.3453(12) 0.8334(4) 0.1305(4) 0.064(2) Uani 1 1 d . . . . .
H15 H 0.4129 0.7935 0.1511 0.077 Uiso 1 1 calc R U . . .
H16 H 0.2475 0.8101 0.1109 0.077 Uiso 1 1 calc R U . . .
N3 N 0.4328(9) 0.8725(4) 0.0717(4) 0.0559(15) Uani 1 1 d . . . . .
H17 H 0.527(8) 0.887(3) 0.080(3) 0.013(12) Uiso 1 1 d . . . . .
C13 C 0.4623(12) 0.8243(5) 0.0056(5) 0.069(2) Uani 1 1 d . . . . .
H18 H 0.3586 0.8081 -0.0144 0.083 Uiso 1 1 calc R U . . .
H19 H 0.5217 0.7790 0.0203 0.083 Uiso 1 1 calc R U . . .
C14 C 0.5560(12) 0.8648(5) -0.0530(5) 0.075(2) Uani 1 1 d . . . . .
H20 H 0.5912 0.8277 -0.0892 0.090 Uiso 1 1 calc R U . . .
H21 H 0.6526 0.8868 -0.0311 0.090 Uiso 1 1 calc R U . . .
C15 C 0.4627(11) 0.9275(5) -0.0923(4) 0.0609(19) Uani 1 1 d . . . . .
H22 H 0.5217 0.9434 -0.1358 0.073 Uiso 1 1 calc R U . . .
H23 H 0.3571 0.9087 -0.1075 0.073 Uiso 1 1 calc R U . . .
N4 N 0.4420(8) 0.9934(3) -0.0416(3) 0.0508(13) Uani 1 1 d . . . . .
C16 C 0.5235(10) 1.0528(4) -0.0527(4) 0.0559(17) Uani 1 1 d . . . . .
H24 H 0.5742 1.0575 -0.0982 0.067 Uiso 1 1 calc R U . . .
C17 C 0.5457(9) 1.1148(4) -0.0007(4) 0.0523(16) Uani 1 1 d . . . . .
C18 C 0.6262(10) 1.1810(5) -0.0229(5) 0.063(2) Uani 1 1 d . . . . .
H25 H 0.6501 1.1872 -0.0726 0.076 Uiso 1 1 calc R U . . .
C19 C 0.6709(13) 1.2365(5) 0.0244(6) 0.078(3) Uani 1 1 d . . . . .
H26 H 0.7292 1.2787 0.0083 0.094 Uiso 1 1 calc R U . . .
C20 C 0.6277(17) 1.2287(6) 0.0965(6) 0.091(3) Uani 1 1 d . . . . .
H27 H 0.6509 1.2678 0.1294 0.109 Uiso 1 1 calc R U . . .
C21 C 0.5490(15) 1.1627(5) 0.1219(5) 0.080(3) Uani 1 1 d . . . . .
H28 H 0.5233 1.1584 0.1715 0.096 Uiso 1 1 calc R U . . .
C22 C 0.5097(10) 1.1052(4) 0.0753(4) 0.0523(16) Uani 1 1 d . . . . .
O2 O 0.4384(7) 1.0426(3) 0.1015(3) 0.0597(13) Uani 1 1 d . . . . .
As1 As 0.17338(12) 1.29861(5) 0.28143(5) 0.0669(3) Uani 1 1 d . . . . .
F1 F 0.2603(18) 1.2444(14) 0.3381(15) 0.388(17) Uani 1 1 d . . . . .
F2 F 0.318(3) 1.2991(10) 0.2222(13) 0.359(18) Uani 1 1 d . . . . .
F3 F 0.114(6) 1.2341(17) 0.2410(18) 0.58(3) Uani 1 1 d . . . . .
F4 F 0.0828(13) 1.3688(8) 0.2302(6) 0.174(5) Uani 1 1 d . . . . .
F5 F 0.0131(15) 1.2908(10) 0.3301(10) 0.272(11) Uani 1 1 d . . . . .
F6 F 0.254(4) 1.3745(10) 0.3158(13) 0.354(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
Mn1 O2 1.854(5) . ?
Mn1 O1 1.874(5) . ?
Mn1 N4 2.098(6) . ?
Mn1 N1 2.105(6) . ?
Mn1 N2 2.180(6) . ?
Mn1 N3 2.240(7) . ?
O1 C1 1.329(8) . ?
C1 C2 1.398(10) . ?
C1 C6 1.416(10) . ?
C2 C3 1.393(12) . ?
C2 H1 0.9300 . ?
C3 C4 1.386(15) . ?
C3 H2 0.9300 . ?
C4 C5 1.366(13) . ?
C4 H3 0.9300 . ?
C5 C6 1.395(10) . ?
C5 H4 0.9300 . ?
C6 C7 1.464(11) . ?
C7 N1 1.280(11) . ?
C7 H5 0.9300 . ?
N1 C8 1.482(9) . ?
C8 C9 1.527(12) . ?
C8 H6 0.9700 . ?
C8 H7 0.9700 . ?
C9 C10 1.512(14) . ?
C9 H8 0.9700 . ?
C9 H9 0.9700 . ?
C10 N2 1.473(10) . ?
C10 H10 0.9700 . ?
C10 H11 0.9700 . ?
N2 C11 1.482(11) . ?
N2 H12 0.88(10) . ?
C11 C12 1.513(12) . ?
C11 H13 0.9700 . ?
C11 H14 0.9700 . ?
C12 N3 1.460(10) . ?
C12 H15 0.9700 . ?
C12 H16 0.9700 . ?
N3 C13 1.490(11) . ?
N3 H17 0.83(6) . ?
C13 C14 1.496(13) . ?
C13 H18 0.9700 . ?
C13 H19 0.9700 . ?
C14 C15 1.520(12) . ?
C14 H20 0.9700 . ?
C14 H21 0.9700 . ?
C15 N4 1.488(9) . ?
C15 H22 0.9700 . ?
C15 H23 0.9700 . ?
N4 C16 1.255(10) . ?
C16 C17 1.454(11) . ?
C16 H24 0.9300 . ?
C17 C18 1.398(11) . ?
C17 C22 1.424(10) . ?
C18 C19 1.350(14) . ?
C18 H25 0.9300 . ?
C19 C20 1.366(15) . ?
C19 H26 0.9300 . ?
C20 C21 1.404(13) . ?
C20 H27 0.9300 . ?
C21 C22 1.357(11) . ?
C21 H28 0.9300 . ?
C22 O2 1.334(9) . ?
As1 F3 1.436(13) . ?
As1 F1 1.574(11) . ?
As1 F5 1.594(9) . ?
As1 F2 1.606(11) . ?
As1 F6 1.616(16) . ?
As1 F4 1.714(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
O2 Mn1 O1 177.9(2) . . ?
O2 Mn1 N4 87.7(2) . . ?
O1 Mn1 N4 92.9(2) . . ?
O2 Mn1 N1 91.5(3) . . ?
O1 Mn1 N1 86.5(2) . . ?
N4 Mn1 N1 108.4(2) . . ?
O2 Mn1 N2 87.9(2) . . ?
O1 Mn1 N2 92.1(2) . . ?
N4 Mn1 N2 165.3(3) . . ?
N1 Mn1 N2 85.7(3) . . ?
O2 Mn1 N3 95.2(3) . . ?
O1 Mn1 N3 86.8(2) . . ?
N4 Mn1 N3 86.0(2) . . ?
N1 Mn1 N3 164.4(3) . . ?
N2 Mn1 N3 80.5(3) . . ?
C1 O1 Mn1 123.2(4) . . ?
O1 C1 C2 118.1(6) . . ?
O1 C1 C6 123.8(6) . . ?
C2 C1 C6 118.0(7) . . ?
C3 C2 C1 120.7(8) . . ?
C3 C2 H1 119.6 . . ?
C1 C2 H1 119.6 . . ?
C4 C3 C2 120.1(8) . . ?
C4 C3 H2 119.9 . . ?
C2 C3 H2 119.9 . . ?
C5 C4 C3 120.2(8) . . ?
C5 C4 H3 119.9 . . ?
C3 C4 H3 119.9 . . ?
C4 C5 C6 120.7(8) . . ?
C4 C5 H4 119.7 . . ?
C6 C5 H4 119.7 . . ?
C5 C6 C1 120.1(7) . . ?
C5 C6 C7 119.1(7) . . ?
C1 C6 C7 120.4(6) . . ?
N1 C7 C6 123.7(7) . . ?
N1 C7 H5 118.2 . . ?
C6 C7 H5 118.2 . . ?
C7 N1 C8 117.7(7) . . ?
C7 N1 Mn1 122.1(5) . . ?
C8 N1 Mn1 120.0(5) . . ?
N1 C8 C9 109.1(6) . . ?
N1 C8 H6 109.9 . . ?
C9 C8 H6 109.9 . . ?
N1 C8 H7 109.9 . . ?
C9 C8 H7 109.9 . . ?
H6 C8 H7 108.3 . . ?
C10 C9 C8 115.5(8) . . ?
C10 C9 H8 108.4 . . ?
C8 C9 H8 108.4 . . ?
C10 C9 H9 108.4 . . ?
C8 C9 H9 108.4 . . ?
H8 C9 H9 107.5 . . ?
N2 C10 C9 112.2(7) . . ?
N2 C10 H10 109.2 . . ?
C9 C10 H10 109.2 . . ?
N2 C10 H11 109.2 . . ?
C9 C10 H11 109.2 . . ?
H10 C10 H11 107.9 . . ?
C10 N2 C11 111.9(6) . . ?
C10 N2 Mn1 117.0(5) . . ?
C11 N2 Mn1 107.1(5) . . ?
C10 N2 H12 94(6) . . ?
C11 N2 H12 113(6) . . ?
Mn1 N2 H12 113(6) . . ?
N2 C11 C12 108.6(6) . . ?
N2 C11 H13 110.0 . . ?
C12 C11 H13 110.0 . . ?
N2 C11 H14 110.0 . . ?
C12 C11 H14 110.0 . . ?
H13 C11 H14 108.4 . . ?
N3 C12 C11 109.5(6) . . ?
N3 C12 H15 109.8 . . ?
C11 C12 H15 109.8 . . ?
N3 C12 H16 109.8 . . ?
C11 C12 H16 109.8 . . ?
H15 C12 H16 108.2 . . ?
C12 N3 C13 113.9(6) . . ?
C12 N3 Mn1 105.4(5) . . ?
C13 N3 Mn1 115.4(5) . . ?
C12 N3 H17 118(4) . . ?
C13 N3 H17 100(4) . . ?
Mn1 N3 H17 104(4) . . ?
N3 C13 C14 112.9(7) . . ?
N3 C13 H18 109.0 . . ?
C14 C13 H18 109.0 . . ?
N3 C13 H19 109.0 . . ?
C14 C13 H19 109.0 . . ?
H18 C13 H19 107.8 . . ?
C13 C14 C15 114.8(7) . . ?
C13 C14 H20 108.6 . . ?
C15 C14 H20 108.6 . . ?
C13 C14 H21 108.6 . . ?
C15 C14 H21 108.6 . . ?
H20 C14 H21 107.6 . . ?
N4 C15 C14 109.3(6) . . ?
N4 C15 H22 109.8 . . ?
C14 C15 H22 109.8 . . ?
N4 C15 H23 109.8 . . ?
C14 C15 H23 109.8 . . ?
H22 C15 H23 108.3 . . ?
C16 N4 C15 118.9(6) . . ?
C16 N4 Mn1 122.1(5) . . ?
C15 N4 Mn1 118.7(5) . . ?
N4 C16 C17 125.7(7) . . ?
N4 C16 H24 117.2 . . ?
C17 C16 H24 117.2 . . ?
C18 C17 C22 118.5(7) . . ?
C18 C17 C16 119.6(7) . . ?
C22 C17 C16 121.2(6) . . ?
C19 C18 C17 123.0(8) . . ?
C19 C18 H25 118.5 . . ?
C17 C18 H25 118.5 . . ?
C18 C19 C20 118.0(8) . . ?
C18 C19 H26 121.0 . . ?
C20 C19 H26 121.0 . . ?
C19 C20 C21 121.2(9) . . ?
C19 C20 H27 119.4 . . ?
C21 C20 H27 119.4 . . ?
C22 C21 C20 121.2(9) . . ?
C22 C21 H28 119.4 . . ?
C20 C21 H28 119.4 . . ?
O2 C22 C21 119.7(7) . . ?
O2 C22 C17 122.4(7) . . ?
C21 C22 C17 117.9(7) . . ?
C22 O2 Mn1 126.3(5) . . ?
F3 As1 F1 91(2) . . ?
F3 As1 F5 86.3(18) . . ?
F1 As1 F5 87.8(6) . . ?
F3 As1 F2 85.0(18) . . ?
F1 As1 F2 96.0(9) . . ?
F5 As1 F2 170.5(14) . . ?
F3 As1 F6 171.4(17) . . ?
F1 As1 F6 93.3(15) . . ?
F5 As1 F6 101.4(15) . . ?
F2 As1 F6 87.1(14) . . ?
F3 As1 F4 98(2) . . ?
F1 As1 F4 170.8(14) . . ?
F5 As1 F4 90.2(5) . . ?
F2 As1 F4 87.4(7) . . ?
F6 As1 F4 78.3(9) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H17 F6 0.83(6) 2.62(6) 3.29(2) 138(5) 4_645
N2 H12 F5 0.88(10) 2.66(10) 3.248(15) 126(8) 4_545

_refine_diff_density_max         0.746
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.090

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1544528'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2017-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H28 Cl Mn N4 O2'
_chemical_formula_weight         470.87

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

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

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

_cell_length_a                   7.5805(10)
_cell_length_b                   16.0064(19)
_cell_length_c                   17.325(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2102.2(4)
_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_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.782
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10749
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.198
_diffrn_reflns_theta_max         28.342
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             2377
_reflns_number_gt                2211
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+7.8077P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2377
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0647
_refine_ls_wR_factor_ref         0.1352
_refine_ls_wR_factor_gt          0.1321
_refine_ls_goodness_of_fit_ref   1.418
_refine_ls_restrained_S_all      1.418
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.2500 0.2500 0.04152(4) 0.00919(18) Uani 1 2 d S T P . .
O1 O 0.3538(3) 0.35639(14) 0.03831(13) 0.0118(5) Uani 1 1 d . . . . .
C1 C 0.4165(4) 0.3978(2) 0.09841(18) 0.0115(6) Uani 1 1 d . . . . .
C2 C 0.4150(5) 0.4857(2) 0.0975(2) 0.0150(7) Uani 1 1 d . . . . .
H1 H 0.3667 0.5143 0.0544 0.018 Uiso 1 1 calc R U . . .
C3 C 0.4826(5) 0.5309(2) 0.1583(2) 0.0163(7) Uani 1 1 d . . . . .
H2 H 0.4753 0.5901 0.1577 0.020 Uiso 1 1 calc R U . . .
C4 C 0.5618(5) 0.4906(2) 0.2209(2) 0.0182(7) Uani 1 1 d . . . . .
H3 H 0.6126 0.5222 0.2617 0.022 Uiso 1 1 calc R U . . .
C5 C 0.5656(5) 0.4048(2) 0.22301(19) 0.0152(7) Uani 1 1 d . . . . .
H4 H 0.6201 0.3773 0.2653 0.018 Uiso 1 1 calc R U . . .
C6 C 0.4898(4) 0.3571(2) 0.16331(18) 0.0120(6) Uani 1 1 d . . . . .
C7 C 0.5095(4) 0.26734(19) 0.16460(18) 0.0119(6) Uani 1 1 d . . . . .
H5 H 0.5851 0.2440 0.2027 0.014 Uiso 1 1 calc R U . . .
N1 N 0.4320(4) 0.21661(17) 0.11790(16) 0.0113(5) Uani 1 1 d . . . . .
C8 C 0.5059(5) 0.1317(2) 0.11313(19) 0.0129(6) Uani 1 1 d . . . . .
H6 H 0.4094 0.0901 0.1157 0.015 Uiso 1 1 calc R U . . .
H7 H 0.5861 0.1218 0.1573 0.015 Uiso 1 1 calc R U . . .
C9 C 0.6068(5) 0.1214(2) 0.0377(2) 0.0160(7) Uani 1 1 d . . . . .
H8 H 0.6703 0.0674 0.0389 0.019 Uiso 1 1 calc R U . . .
H9 H 0.6963 0.1663 0.0341 0.019 Uiso 1 1 calc R U . . .
C10 C 0.4919(5) 0.1241(2) -0.03436(19) 0.0162(7) Uani 1 1 d . . . . .
H10 H 0.5648 0.1105 -0.0801 0.019 Uiso 1 1 calc R U . . .
H11 H 0.3981 0.0813 -0.0301 0.019 Uiso 1 1 calc R U . . .
N2 N 0.4099(4) 0.20728(17) -0.04533(15) 0.0124(6) Uani 1 1 d . . . . .
H12 H 0.5076 0.2486 -0.0517 0.015 Uiso 1 1 calc R U . . .
C11 C 0.3025(5) 0.2099(2) -0.11650(19) 0.0169(7) Uani 1 1 d . . . . .
H13 H 0.2218 0.1613 -0.1182 0.020 Uiso 1 1 calc R U . . .
H14 H 0.3800 0.2077 -0.1624 0.020 Uiso 1 1 calc R U . . .
Cl1 Cl 0.7500 0.2500 0.85423(6) 0.0155(2) Uani 1 2 d S T P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O1 1.877(2) 2 ?
Mn1 O1 1.877(2) . ?
Mn1 N1 1.985(3) 2 ?
Mn1 N1 1.985(3) . ?
Mn1 N2 2.049(3) . ?
Mn1 N2 2.049(3) 2 ?
O1 C1 1.323(4) . ?
C1 C2 1.408(5) . ?
C1 C6 1.413(4) . ?
C2 C3 1.377(5) . ?
C2 H1 0.9500 . ?
C3 C4 1.398(5) . ?
C3 H2 0.9500 . ?
C4 C5 1.373(5) . ?
C4 H3 0.9500 . ?
C5 C6 1.408(5) . ?
C5 H4 0.9500 . ?
C6 C7 1.445(4) . ?
C7 N1 1.288(4) . ?
C7 H5 0.9500 . ?
N1 C8 1.472(4) . ?
C8 C9 1.523(5) . ?
C8 H6 0.9900 . ?
C8 H7 0.9900 . ?
C9 C10 1.523(5) . ?
C9 H8 0.9900 . ?
C9 H9 0.9900 . ?
C10 N2 1.482(4) . ?
C10 H10 0.9900 . ?
C10 H11 0.9900 . ?
N2 C11 1.478(4) . ?
N2 H12 1.0000 . ?
C11 C11 1.511(7) 2 ?
C11 H13 0.9900 . ?
C11 H14 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Mn1 O1 176.60(14) 2 . ?
O1 Mn1 N1 88.44(11) 2 2 ?
O1 Mn1 N1 93.83(11) . 2 ?
O1 Mn1 N1 93.83(11) 2 . ?
O1 Mn1 N1 88.44(11) . . ?
N1 Mn1 N1 96.39(16) 2 . ?
O1 Mn1 N2 85.60(10) 2 . ?
O1 Mn1 N2 91.90(10) . . ?
N1 Mn1 N2 171.99(11) 2 . ?
N1 Mn1 N2 89.34(11) . . ?
O1 Mn1 N2 91.90(10) 2 2 ?
O1 Mn1 N2 85.60(10) . 2 ?
N1 Mn1 N2 89.35(11) 2 2 ?
N1 Mn1 N2 171.99(11) . 2 ?
N2 Mn1 N2 85.52(16) . 2 ?
C1 O1 Mn1 125.6(2) . . ?
O1 C1 C2 119.3(3) . . ?
O1 C1 C6 122.5(3) . . ?
C2 C1 C6 118.2(3) . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 H1 119.5 . . ?
C1 C2 H1 119.5 . . ?
C2 C3 C4 120.8(3) . . ?
C2 C3 H2 119.6 . . ?
C4 C3 H2 119.6 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H3 120.3 . . ?
C3 C4 H3 120.3 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H4 119.5 . . ?
C6 C5 H4 119.5 . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 C7 119.1(3) . . ?
C1 C6 C7 120.7(3) . . ?
N1 C7 C6 124.8(3) . . ?
N1 C7 H5 117.6 . . ?
C6 C7 H5 117.6 . . ?
C7 N1 C8 116.3(3) . . ?
C7 N1 Mn1 124.5(2) . . ?
C8 N1 Mn1 118.4(2) . . ?
N1 C8 C9 109.8(3) . . ?
N1 C8 H6 109.7 . . ?
C9 C8 H6 109.7 . . ?
N1 C8 H7 109.7 . . ?
C9 C8 H7 109.7 . . ?
H6 C8 H7 108.2 . . ?
C8 C9 C10 114.4(3) . . ?
C8 C9 H8 108.7 . . ?
C10 C9 H8 108.7 . . ?
C8 C9 H9 108.7 . . ?
C10 C9 H9 108.7 . . ?
H8 C9 H9 107.6 . . ?
N2 C10 C9 111.7(3) . . ?
N2 C10 H10 109.3 . . ?
C9 C10 H10 109.3 . . ?
N2 C10 H11 109.3 . . ?
C9 C10 H11 109.3 . . ?
H10 C10 H11 107.9 . . ?
C11 N2 C10 111.3(3) . . ?
C11 N2 Mn1 106.1(2) . . ?
C10 N2 Mn1 117.0(2) . . ?
C11 N2 H12 107.3 . . ?
C10 N2 H12 107.3 . . ?
Mn1 N2 H12 107.3 . . ?
N2 C11 C11 108.3(2) . 2 ?
N2 C11 H13 110.0 . . ?
C11 C11 H13 110.0 2 . ?
N2 C11 H14 110.0 . . ?
C11 C11 H14 110.0 2 . ?
H13 C11 H14 108.4 . . ?

_refine_diff_density_max         0.468
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.095

####################################################################### 
# 
# 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_P2N
_database_code_depnum_ccdc_archive 'CCDC 1544525'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2017-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H28 F6 Mn N4 O2 Sb'
_chemical_formula_weight         671.17

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/n'
_space_group_name_Hall           '-P 2yac'

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

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

_cell_length_a                   11.661(4)
_cell_length_b                   8.205(3)
_cell_length_c                   13.538(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.153(7)
_cell_angle_gamma                90
_cell_volume                     1291.9(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(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_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_F_000             668
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    1.604
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.749
_exptl_absorpt_correction_T_max  0.825
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6760
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.227
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_full        24.992
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             2176
_reflns_number_gt                2046
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0252P)²+1.8815P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2176
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0799
_refine_ls_wR_factor_gt          0.0789
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.2500 0.67391(9) 0.7500 0.03229(18) Uani 1 2 d S T P . .
O1 O 0.2020(2) 0.6730(3) 0.61633(17) 0.0403(6) Uani 1 1 d . . . . .
C1 C 0.1717(3) 0.5372(4) 0.5671(2) 0.0356(7) Uani 1 1 d . . . . .
C2 C 0.2034(3) 0.5177(5) 0.4707(3) 0.0475(9) Uani 1 1 d . . . . .
H1 H 0.2450 0.5992 0.4417 0.057 Uiso 1 1 calc R U . . .
C3 C 0.1739(3) 0.3796(6) 0.4180(3) 0.0547(11) Uani 1 1 d . . . . .
H2 H 0.1977 0.3676 0.3543 0.066 Uiso 1 1 calc R U . . .
C4 C 0.1102(4) 0.2588(5) 0.4572(3) 0.0596(11) Uani 1 1 d . . . . .
H3 H 0.0918 0.1650 0.4209 0.072 Uiso 1 1 calc R U . . .
C5 C 0.0732(3) 0.2774(5) 0.5513(3) 0.0491(9) Uani 1 1 d . . . . .
H4 H 0.0264 0.1984 0.5768 0.059 Uiso 1 1 calc R U . . .
C6 C 0.1058(3) 0.4147(4) 0.6084(3) 0.0359(7) Uani 1 1 d . . . . .
C7 C 0.0621(3) 0.4338(4) 0.7050(3) 0.0392(8) Uani 1 1 d . . . . .
H5 H -0.0011 0.3713 0.7193 0.047 Uiso 1 1 calc R U . . .
N1 N 0.1043(2) 0.5301(4) 0.7716(2) 0.0372(6) Uani 1 1 d . . . . .
C8 C 0.0416(3) 0.5531(6) 0.8615(3) 0.0540(10) Uani 1 1 d . . . . .
H6 H 0.0940 0.5377 0.9197 0.065 Uiso 1 1 calc R U . . .
H7 H -0.0187 0.4719 0.8630 0.065 Uiso 1 1 calc R U . . .
C9 C -0.0110(3) 0.7217(7) 0.8642(3) 0.0678(14) Uani 1 1 d . . . . .
H8 H -0.0598 0.7371 0.8038 0.081 Uiso 1 1 calc R U . . .
H9 H -0.0599 0.7261 0.9191 0.081 Uiso 1 1 calc R U . . .
C10 C 0.0724(4) 0.8622(6) 0.8743(3) 0.0690(14) Uani 1 1 d . . . . .
H10 H 0.0303 0.9616 0.8857 0.083 Uiso 1 1 calc R U . . .
H11 H 0.1258 0.8439 0.9316 0.083 Uiso 1 1 calc R U . . .
N2 N 0.1377(3) 0.8833(4) 0.7861(3) 0.0568(9) Uani 1 1 d . . . . .
C11 C 0.2117(5) 1.0295(6) 0.7917(4) 0.0803(16) Uani 1 1 d . . . . .
H12 H 0.2578 1.0305 0.8542 0.096 Uiso 1 1 calc R U . . .
H13 H 0.1642 1.1267 0.7884 0.096 Uiso 1 1 calc R U . . .
Sb1 Sb 0.2500 0.90071(4) 0.2500 0.03891(14) Uani 1 2 d S T P . .
F1 F 0.2500 1.1279(4) 0.2500 0.0574(8) Uani 1 2 d S T P . .
F2 F 0.0992(2) 0.9054(4) 0.2899(2) 0.0809(9) Uani 1 1 d . . . . .
F3 F 0.2500 0.6730(4) 0.2500 0.0809(12) Uani 1 2 d S T P . .
F4 F 0.1923(3) 0.9006(4) 0.1202(2) 0.0875(10) Uani 1 1 d . . . . .
H14 H 0.091(4) 0.891(5) 0.738(3) 0.046(11) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O1 1.855(2) . ?
Mn1 O1 1.855(2) 2_556 ?
Mn1 N1 2.107(3) 2_556 ?
Mn1 N1 2.107(3) . ?
Mn1 N2 2.236(3) 2_556 ?
Mn1 N2 2.236(3) . ?
O1 C1 1.333(4) . ?
C1 C2 1.392(5) . ?
C1 C6 1.405(5) . ?
C2 C3 1.369(6) . ?
C2 H1 0.9300 . ?
C3 C4 1.369(6) . ?
C3 H2 0.9300 . ?
C4 C5 1.382(6) . ?
C4 H3 0.9300 . ?
C5 C6 1.403(5) . ?
C5 H4 0.9300 . ?
C6 C7 1.445(5) . ?
C7 N1 1.271(4) . ?
C7 H5 0.9300 . ?
N1 C8 1.477(5) . ?
C8 C9 1.515(7) . ?
C8 H6 0.9700 . ?
C8 H7 0.9700 . ?
C9 C10 1.507(7) . ?
C9 H8 0.9700 . ?
C9 H9 0.9700 . ?
C10 N2 1.473(6) . ?
C10 H10 0.9700 . ?
C10 H11 0.9700 . ?
N2 C11 1.477(6) . ?
N2 H14 0.82(4) . ?
C11 C11 1.489(12) 2_556 ?
C11 H12 0.9700 . ?
C11 H13 0.9700 . ?
Sb1 F4 1.836(3) . ?
Sb1 F4 1.836(3) 2 ?
Sb1 F1 1.864(3) . ?
Sb1 F3 1.869(4) . ?
Sb1 F2 1.876(2) 2 ?
Sb1 F2 1.876(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Mn1 O1 179.52(15) . 2_556 ?
O1 Mn1 N1 92.96(11) . 2_556 ?
O1 Mn1 N1 86.77(10) 2_556 2_556 ?
O1 Mn1 N1 86.77(10) . . ?
O1 Mn1 N1 92.96(11) 2_556 . ?
N1 Mn1 N1 111.85(17) 2_556 . ?
O1 Mn1 N2 86.00(12) . 2_556 ?
O1 Mn1 N2 94.36(12) 2_556 2_556 ?
N1 Mn1 N2 84.77(14) 2_556 2_556 ?
N1 Mn1 N2 162.20(13) . 2_556 ?
O1 Mn1 N2 94.37(12) . . ?
O1 Mn1 N2 86.01(12) 2_556 . ?
N1 Mn1 N2 162.20(13) 2_556 . ?
N1 Mn1 N2 84.77(14) . . ?
N2 Mn1 N2 79.6(2) 2_556 . ?
C1 O1 Mn1 122.8(2) . . ?
O1 C1 C2 119.1(3) . . ?
O1 C1 C6 122.1(3) . . ?
C2 C1 C6 118.7(3) . . ?
C3 C2 C1 120.7(4) . . ?
C3 C2 H1 119.7 . . ?
C1 C2 H1 119.7 . . ?
C2 C3 C4 121.3(4) . . ?
C2 C3 H2 119.3 . . ?
C4 C3 H2 119.3 . . ?
C3 C4 C5 119.5(4) . . ?
C3 C4 H3 120.3 . . ?
C5 C4 H3 120.3 . . ?
C4 C5 C6 120.4(4) . . ?
C4 C5 H4 119.8 . . ?
C6 C5 H4 119.8 . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 C7 119.1(3) . . ?
C1 C6 C7 121.4(3) . . ?
N1 C7 C6 124.5(3) . . ?
N1 C7 H5 117.8 . . ?
C6 C7 H5 117.8 . . ?
C7 N1 C8 118.4(3) . . ?
C7 N1 Mn1 121.6(2) . . ?
C8 N1 Mn1 119.7(2) . . ?
N1 C8 C9 111.2(3) . . ?
N1 C8 H6 109.4 . . ?
C9 C8 H6 109.4 . . ?
N1 C8 H7 109.4 . . ?
C9 C8 H7 109.4 . . ?
H6 C8 H7 108.0 . . ?
C10 C9 C8 116.2(3) . . ?
C10 C9 H8 108.2 . . ?
C8 C9 H8 108.2 . . ?
C10 C9 H9 108.2 . . ?
C8 C9 H9 108.2 . . ?
H8 C9 H9 107.4 . . ?
N2 C10 C9 112.6(3) . . ?
N2 C10 H10 109.1 . . ?
C9 C10 H10 109.1 . . ?
N2 C10 H11 109.1 . . ?
C9 C10 H11 109.1 . . ?
H10 C10 H11 107.8 . . ?
C10 N2 C11 112.8(4) . . ?
C10 N2 Mn1 115.6(3) . . ?
C11 N2 Mn1 106.6(3) . . ?
C10 N2 H14 108(3) . . ?
C11 N2 H14 109(3) . . ?
Mn1 N2 H14 105(3) . . ?
N2 C11 C11 110.0(3) . 2_556 ?
N2 C11 H12 109.7 . . ?
C11 C11 H12 109.7 2_556 . ?
N2 C11 H13 109.7 . . ?
C11 C11 H13 109.7 2_556 . ?
H12 C11 H13 108.2 . . ?
F4 Sb1 F4 179.93(19) . 2 ?
F4 Sb1 F1 90.04(9) . . ?
F4 Sb1 F1 90.04(9) 2 . ?
F4 Sb1 F3 89.96(9) . . ?
F4 Sb1 F3 89.96(9) 2 . ?
F1 Sb1 F3 180.0 . . ?
F4 Sb1 F2 90.62(16) . 2 ?
F4 Sb1 F2 89.38(16) 2 2 ?
F1 Sb1 F2 88.84(9) . 2 ?
F3 Sb1 F2 91.16(9) . 2 ?
F4 Sb1 F2 89.38(16) . . ?
F4 Sb1 F2 90.62(16) 2 . ?
F1 Sb1 F2 88.84(9) . . ?
F3 Sb1 F2 91.16(9) . . ?
F2 Sb1 F2 177.67(18) 2 . ?

_refine_diff_density_max         0.492
_refine_diff_density_min         -1.018
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1544518'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2017-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H28 As F6 Mn N4 O2'
_chemical_formula_weight         624.34

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'
As As 0.0499 2.0058 '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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   8.2852(5)
_cell_length_b                   17.2151(10)
_cell_length_c                   17.7965(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2538.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    146(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_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    1.885
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.719
_exptl_absorpt_correction_T_max  0.813
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      146(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22548
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.646
_diffrn_reflns_theta_max         28.311
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6303
_reflns_number_gt                5686
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2319 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(4)
_chemical_absolute_configuration .
_refine_ls_number_reflns         6303
_refine_ls_number_parameters     411
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.1059
_refine_ls_wR_factor_gt          0.0978
_refine_ls_goodness_of_fit_ref   0.852
_refine_ls_restrained_S_all      0.852
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6820(3) 0.41748(15) 0.00646(16) 0.0209(5) Uani 1 1 d . . . . .
C1 C 0.5891(4) 0.4419(2) -0.0486(2) 0.0216(7) Uani 1 1 d . . . . .
C2 C 0.5312(5) 0.3886(3) -0.1020(3) 0.0271(8) Uani 1 1 d . . . . .
H1 H 0.569(7) 0.338(3) -0.096(3) 0.032 Uiso 1 1 d . U . . .
C3 C 0.4354(6) 0.4110(3) -0.1608(3) 0.0318(9) Uani 1 1 d . . . . .
H2 H 0.410(7) 0.374(4) -0.195(3) 0.038 Uiso 1 1 d . U . . .
C4 C 0.3912(6) 0.4886(3) -0.1701(2) 0.0340(10) Uani 1 1 d . . . . .
H3 H 0.328(7) 0.508(3) -0.215(4) 0.041 Uiso 1 1 d . U . . .
C5 C 0.4439(6) 0.5423(3) -0.1181(3) 0.0324(9) Uani 1 1 d . . . . .
H4 H 0.421(8) 0.600(3) -0.127(3) 0.039 Uiso 1 1 d . U . . .
C6 C 0.5416(5) 0.5206(3) -0.0571(2) 0.0261(8) Uani 1 1 d . . . . .
C7 C 0.5765(6) 0.5762(2) 0.0012(3) 0.0317(9) Uani 1 1 d . . . . .
H5 H 0.508(8) 0.619(3) 0.002(3) 0.038 Uiso 1 1 d . U . . .
N1 N 0.6858(5) 0.56775(19) 0.0518(2) 0.0288(8) Uani 1 1 d . . . . .
C8 C 0.6791(7) 0.6200(2) 0.1177(3) 0.0337(10) Uani 1 1 d . . . . .
H6 H 0.607(7) 0.660(4) 0.114(4) 0.041 Uiso 1 1 d . U . . .
H7 H 0.804(7) 0.641(4) 0.123(3) 0.041 Uiso 1 1 d . U . . .
C9 C 0.6170(7) 0.5740(3) 0.1864(3) 0.0359(10) Uani 1 1 d . . . . .
H8 H 0.610(8) 0.619(4) 0.225(4) 0.043 Uiso 1 1 d . U . . .
H9 H 0.505(8) 0.562(4) 0.173(4) 0.043 Uiso 1 1 d . U . . .
C10 C 0.7334(5) 0.5122(2) 0.2137(2) 0.0268(8) Uani 1 1 d . . . . .
H10 H 0.850(7) 0.545(3) 0.219(3) 0.032 Uiso 1 1 d . U . . .
H11 H 0.692(7) 0.483(3) 0.263(3) 0.032 Uiso 1 1 d . U . . .
N2 N 0.7521(4) 0.4482(2) 0.1590(2) 0.0215(6) Uani 1 1 d . . . . .
H12 H 0.656(7) 0.427(3) 0.153(3) 0.034(14) Uiso 1 1 d . . . . .
C11 C 0.8558(6) 0.3859(2) 0.1899(2) 0.0247(8) Uani 1 1 d . . . . .
H13 H 0.801(7) 0.362(3) 0.230(3) 0.030 Uiso 1 1 d . U . . .
H14 H 0.950(7) 0.403(3) 0.207(3) 0.030 Uiso 1 1 d . U . . .
C12 C 0.8957(5) 0.3297(2) 0.1278(2) 0.0248(8) Uani 1 1 d . . . . .
H15 H 0.972(7) 0.297(3) 0.141(3) 0.030 Uiso 1 1 d . U . . .
H16 H 0.796(7) 0.316(3) 0.113(3) 0.030 Uiso 1 1 d . U . . .
N3 N 0.9726(4) 0.3732(2) 0.0646(2) 0.0225(7) Uani 1 1 d . . . . .
H17 H 1.062(6) 0.387(3) 0.078(2) 0.010(10) Uiso 1 1 d . . . . .
C13 C 0.9908(5) 0.3239(3) -0.0030(3) 0.0272(8) Uani 1 1 d . . . . .
H18 H 0.894(7) 0.319(3) -0.022(3) 0.033 Uiso 1 1 d . U . . .
H19 H 1.056(7) 0.278(3) 0.007(3) 0.033 Uiso 1 1 d . U . . .
C14 C 1.0682(6) 0.3677(3) -0.0682(2) 0.0281(9) Uani 1 1 d . . . . .
H20 H 1.176(7) 0.387(3) -0.052(3) 0.034 Uiso 1 1 d . U . . .
H21 H 1.092(7) 0.334(3) -0.110(3) 0.034 Uiso 1 1 d . U . . .
C15 C 0.9681(5) 0.4334(3) -0.0994(2) 0.0258(8) Uani 1 1 d . . . . .
H22 H 1.017(7) 0.445(3) -0.147(3) 0.031 Uiso 1 1 d . U . . .
H23 H 0.864(7) 0.411(3) -0.113(3) 0.031 Uiso 1 1 d . U . . .
N4 N 0.9571(4) 0.4970(2) -0.04396(19) 0.0232(7) Uani 1 1 d . . . . .
C16 C 1.0420(5) 0.5575(2) -0.0570(2) 0.0250(8) Uani 1 1 d . . . . .
H24 H 1.096(7) 0.569(3) -0.107(3) 0.030 Uiso 1 1 d . U . . .
C17 C 1.0870(5) 0.6154(2) -0.0013(2) 0.0226(7) Uani 1 1 d . . . . .
C18 C 1.1676(6) 0.6824(3) -0.0244(3) 0.0297(8) Uani 1 1 d . . . . .
H25 H 1.175(7) 0.689(4) -0.076(3) 0.036 Uiso 1 1 d . U . . .
C19 C 1.2349(6) 0.7333(3) 0.0267(3) 0.0346(10) Uani 1 1 d . . . . .
H26 H 1.290(7) 0.781(3) 0.012(4) 0.042 Uiso 1 1 d . U . . .
C20 C 1.2262(8) 0.7146(3) 0.1032(3) 0.0451(13) Uani 1 1 d . . . . .
H27 H 1.288(9) 0.737(4) 0.135(4) 0.054 Uiso 1 1 d . U . . .
C21 C 1.1480(8) 0.6489(3) 0.1269(3) 0.0417(12) Uani 1 1 d . . . . .
H28 H 1.138(8) 0.633(4) 0.181(4) 0.050 Uiso 1 1 d . U . . .
C22 C 1.0741(5) 0.5981(3) 0.0765(2) 0.0274(8) Uani 1 1 d . . . . .
O2 O 1.0034(4) 0.53451(18) 0.10247(16) 0.0279(6) Uani 1 1 d . . . . .
Mn1 Mn 0.84182(7) 0.47732(3) 0.05329(3) 0.01820(14) Uani 1 1 d . . . . .
As1 As 0.36891(5) 0.31344(2) 0.21547(2) 0.02541(13) Uani 1 1 d . . . . .
F1 F 0.4626(5) 0.3888(2) 0.2609(2) 0.0576(10) Uani 1 1 d . . . . .
F2 F 0.2515(6) 0.3789(3) 0.1708(4) 0.102(2) Uani 1 1 d . . . . .
F3 F 0.2262(7) 0.3091(4) 0.2831(3) 0.116(3) Uani 1 1 d . . . . .
F4 F 0.2778(5) 0.2384(2) 0.1703(3) 0.0698(13) Uani 1 1 d . . . . .
F5 F 0.4903(8) 0.2513(3) 0.2609(5) 0.144(3) Uani 1 1 d . . . . .
F6 F 0.5084(5) 0.3205(3) 0.1456(2) 0.0760(15) 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
O1 C1 1.316(5) . ?
O1 Mn1 1.873(3) . ?
C1 C2 1.405(6) . ?
C1 C6 1.418(6) . ?
C2 C3 1.369(7) . ?
C2 H1 0.93(6) . ?
C3 C4 1.395(7) . ?
C3 H2 0.91(6) . ?
C4 C5 1.379(7) . ?
C4 H3 1.02(6) . ?
C5 C6 1.405(6) . ?
C5 H4 1.01(6) . ?
C6 C7 1.442(6) . ?
C7 N1 1.285(6) . ?
C7 H5 0.93(6) . ?
N1 C8 1.479(6) . ?
N1 Mn1 2.023(4) . ?
C8 C9 1.545(7) . ?
C8 H6 0.92(6) . ?
C8 H7 1.10(6) . ?
C9 C10 1.516(7) . ?
C9 H8 1.05(6) . ?
C9 H9 0.98(7) . ?
C10 N2 1.479(5) . ?
C10 H10 1.12(6) . ?
C10 H11 1.06(6) . ?
N2 C11 1.479(5) . ?
N2 Mn1 2.085(4) . ?
N2 H12 0.89(6) . ?
C11 C12 1.507(6) . ?
C11 H13 0.94(6) . ?
C11 H14 0.89(6) . ?
C12 N3 1.493(5) . ?
C12 H15 0.88(6) . ?
C12 H16 0.90(6) . ?
N3 C13 1.480(5) . ?
N3 Mn1 2.104(4) . ?
N3 H17 0.81(5) . ?
C13 C14 1.524(6) . ?
C13 H18 0.88(6) . ?
C13 H19 0.97(6) . ?
C14 C15 1.509(7) . ?
C14 H20 0.99(6) . ?
C14 H21 0.96(6) . ?
C15 N4 1.476(5) . ?
C15 H22 0.95(6) . ?
C15 H23 0.98(6) . ?
N4 C16 1.277(5) . ?
N4 Mn1 2.006(3) . ?
C16 C17 1.454(6) . ?
C16 H24 1.01(6) . ?
C17 C18 1.396(6) . ?
C17 C22 1.420(6) . ?
C18 C19 1.380(7) . ?
C18 H25 0.93(6) . ?
C19 C20 1.401(8) . ?
C19 H26 0.98(6) . ?
C20 C21 1.370(8) . ?
C20 H27 0.87(8) . ?
C21 C22 1.396(6) . ?
C21 H28 1.00(7) . ?
C22 O2 1.324(5) . ?
O2 Mn1 1.878(3) . ?
As1 F5 1.676(5) . ?
As1 F2 1.688(4) . ?
As1 F3 1.689(4) . ?
As1 F4 1.699(3) . ?
As1 F6 1.703(3) . ?
As1 F1 1.714(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 Mn1 124.7(2) . . ?
O1 C1 C2 119.6(4) . . ?
O1 C1 C6 123.2(4) . . ?
C2 C1 C6 117.2(4) . . ?
C3 C2 C1 122.1(4) . . ?
C3 C2 H1 123(4) . . ?
C1 C2 H1 115(4) . . ?
C2 C3 C4 120.8(4) . . ?
C2 C3 H2 117(4) . . ?
C4 C3 H2 122(4) . . ?
C5 C4 C3 118.7(4) . . ?
C5 C4 H3 118(3) . . ?
C3 C4 H3 123(4) . . ?
C4 C5 C6 121.4(4) . . ?
C4 C5 H4 120(3) . . ?
C6 C5 H4 119(3) . . ?
C5 C6 C1 119.8(4) . . ?
C5 C6 C7 119.7(4) . . ?
C1 C6 C7 120.1(4) . . ?
N1 C7 C6 124.8(4) . . ?
N1 C7 H5 120(4) . . ?
C6 C7 H5 115(4) . . ?
C7 N1 C8 117.4(4) . . ?
C7 N1 Mn1 123.1(3) . . ?
C8 N1 Mn1 118.8(3) . . ?
N1 C8 C9 109.3(3) . . ?
N1 C8 H6 116(4) . . ?
C9 C8 H6 103(4) . . ?
N1 C8 H7 104(3) . . ?
C9 C8 H7 114(3) . . ?
H6 C8 H7 112(5) . . ?
C10 C9 C8 113.6(4) . . ?
C10 C9 H8 110(4) . . ?
C8 C9 H8 99(3) . . ?
C10 C9 H9 122(4) . . ?
C8 C9 H9 103(4) . . ?
H8 C9 H9 105(5) . . ?
N2 C10 C9 112.3(4) . . ?
N2 C10 H10 110(3) . . ?
C9 C10 H10 103(3) . . ?
N2 C10 H11 103(3) . . ?
C9 C10 H11 113(3) . . ?
H10 C10 H11 117(4) . . ?
C10 N2 C11 110.9(3) . . ?
C10 N2 Mn1 116.9(3) . . ?
C11 N2 Mn1 107.6(2) . . ?
C10 N2 H12 107(4) . . ?
C11 N2 H12 106(4) . . ?
Mn1 N2 H12 108(4) . . ?
N2 C11 C12 108.7(3) . . ?
N2 C11 H13 109(3) . . ?
C12 C11 H13 112(3) . . ?
N2 C11 H14 113(4) . . ?
C12 C11 H14 105(4) . . ?
H13 C11 H14 109(5) . . ?
N3 C12 C11 108.9(3) . . ?
N3 C12 H15 103(4) . . ?
C11 C12 H15 112(4) . . ?
N3 C12 H16 107(4) . . ?
C11 C12 H16 101(4) . . ?
H15 C12 H16 125(5) . . ?
C13 N3 C12 111.6(3) . . ?
C13 N3 Mn1 117.5(3) . . ?
C12 N3 Mn1 106.3(2) . . ?
C13 N3 H17 108(3) . . ?
C12 N3 H17 109(3) . . ?
Mn1 N3 H17 104(3) . . ?
N3 C13 C14 112.2(3) . . ?
N3 C13 H18 107(4) . . ?
C14 C13 H18 98(4) . . ?
N3 C13 H19 112(3) . . ?
C14 C13 H19 108(3) . . ?
H18 C13 H19 120(5) . . ?
C15 C14 C13 114.8(4) . . ?
C15 C14 H20 111(3) . . ?
C13 C14 H20 108(3) . . ?
C15 C14 H21 107(3) . . ?
C13 C14 H21 112(3) . . ?
H20 C14 H21 104(5) . . ?
N4 C15 C14 110.1(3) . . ?
N4 C15 H22 117(4) . . ?
C14 C15 H22 104(3) . . ?
N4 C15 H23 114(3) . . ?
C14 C15 H23 106(3) . . ?
H22 C15 H23 104(5) . . ?
C16 N4 C15 116.7(4) . . ?
C16 N4 Mn1 123.8(3) . . ?
C15 N4 Mn1 118.7(3) . . ?
N4 C16 C17 125.1(4) . . ?
N4 C16 H24 124(3) . . ?
C17 C16 H24 111(3) . . ?
C18 C17 C22 119.8(4) . . ?
C18 C17 C16 119.2(4) . . ?
C22 C17 C16 120.1(4) . . ?
C19 C18 C17 121.6(4) . . ?
C19 C18 H25 123(4) . . ?
C17 C18 H25 115(4) . . ?
C18 C19 C20 118.3(4) . . ?
C18 C19 H26 123(4) . . ?
C20 C19 H26 119(4) . . ?
C21 C20 C19 121.0(5) . . ?
C21 C20 H27 117(5) . . ?
C19 C20 H27 121(5) . . ?
C20 C21 C22 121.7(5) . . ?
C20 C21 H28 124(4) . . ?
C22 C21 H28 114(4) . . ?
O2 C22 C21 119.2(4) . . ?
O2 C22 C17 123.2(4) . . ?
C21 C22 C17 117.6(4) . . ?
C22 O2 Mn1 125.8(3) . . ?
O1 Mn1 O2 178.06(13) . . ?
O1 Mn1 N4 92.62(13) . . ?
O2 Mn1 N4 88.51(13) . . ?
O1 Mn1 N1 88.03(13) . . ?
O2 Mn1 N1 93.33(15) . . ?
N4 Mn1 N1 99.35(15) . . ?
O1 Mn1 N2 90.98(13) . . ?
O2 Mn1 N2 87.69(13) . . ?
N4 Mn1 N2 171.68(14) . . ?
N1 Mn1 N2 88.25(14) . . ?
O1 Mn1 N3 86.45(13) . . ?
O2 Mn1 N3 92.01(14) . . ?
N4 Mn1 N3 88.95(14) . . ?
N1 Mn1 N3 170.23(15) . . ?
N2 Mn1 N3 83.80(14) . . ?
F5 As1 F2 177.7(3) . . ?
F5 As1 F3 92.8(4) . . ?
F2 As1 F3 87.8(4) . . ?
F5 As1 F4 90.6(3) . . ?
F2 As1 F4 91.6(3) . . ?
F3 As1 F4 89.5(2) . . ?
F5 As1 F6 89.5(4) . . ?
F2 As1 F6 89.9(3) . . ?
F3 As1 F6 177.8(3) . . ?
F4 As1 F6 90.58(18) . . ?
F5 As1 F1 89.1(3) . . ?
F2 As1 F1 88.7(3) . . ?
F3 As1 F1 90.9(2) . . ?
F4 As1 F1 179.5(2) . . ?
F6 As1 F1 89.02(17) . . ?

_refine_diff_density_max         0.691
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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 1544523'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2017-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H28 F6 Mn N4 O2 Sb'
_chemical_formula_weight         671.17

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/n'
_space_group_name_Hall           '-P 2yac'

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

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

_cell_length_a                   11.5228(12)
_cell_length_b                   8.1611(9)
_cell_length_c                   13.4565(14)
_cell_angle_alpha                90
_cell_angle_beta                 93.442(2)
_cell_angle_gamma                90
_cell_volume                     1263.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(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_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_F_000             668
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    1.641
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.744
_exptl_absorpt_correction_T_max  0.821
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10162
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.261
_diffrn_reflns_theta_max         28.252
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3098
_reflns_number_gt                2975
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0192P)²+0.8222P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3098
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0198
_refine_ls_R_factor_gt           0.0187
_refine_ls_wR_factor_ref         0.0471
_refine_ls_wR_factor_gt          0.0464
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.136
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.20215(9) 0.18142(12) 0.11540(8) 0.0127(2) Uani 1 1 d . . . . .
C1 C 0.17230(12) 0.04463(17) 0.06612(10) 0.0113(3) Uani 1 1 d . . . . .
C2 C 0.20564(12) 0.02641(18) -0.03198(11) 0.0147(3) Uani 1 1 d . . . . .
H1 H 0.2485 0.1110 -0.0616 0.018 Uiso 1 1 calc R U . . .
C3 C 0.17660(13) -0.11350(19) -0.08574(11) 0.0169(3) Uani 1 1 d . . . . .
H2 H 0.2016 -0.1251 -0.1514 0.020 Uiso 1 1 calc R U . . .
C4 C 0.11118(13) -0.23818(19) -0.04522(12) 0.0179(3) Uani 1 1 d . . . . .
H3 H 0.0926 -0.3345 -0.0825 0.022 Uiso 1 1 calc R U . . .
C5 C 0.07384(13) -0.21953(18) 0.04987(12) 0.0161(3) Uani 1 1 d . . . . .
H4 H 0.0262 -0.3015 0.0767 0.019 Uiso 1 1 calc R U . . .
C6 C 0.10537(12) -0.08077(17) 0.10749(11) 0.0122(3) Uani 1 1 d . . . . .
C7 C 0.06013(12) -0.06274(18) 0.20532(11) 0.0132(3) Uani 1 1 d . . . . .
H5 H -0.0049 -0.1277 0.2204 0.016 Uiso 1 1 calc R U . . .
N1 N 0.10252(10) 0.03539(15) 0.27267(9) 0.0130(2) Uani 1 1 d . . . . .
C8 C 0.03889(13) 0.0565(2) 0.36362(11) 0.0166(3) Uani 1 1 d . . . . .
H6 H 0.0929 0.0405 0.4229 0.020 Uiso 1 1 calc R U . . .
H7 H -0.0231 -0.0274 0.3653 0.020 Uiso 1 1 calc R U . . .
C9 C -0.01524(13) 0.2272(2) 0.36716(12) 0.0209(3) Uani 1 1 d . . . . .
H8 H -0.0657 0.2431 0.3057 0.025 Uiso 1 1 calc R U . . .
H9 H -0.0657 0.2311 0.4241 0.025 Uiso 1 1 calc R U . . .
C10 C 0.06973(14) 0.3701(2) 0.37685(12) 0.0204(3) Uani 1 1 d . . . . .
H10 H 0.0262 0.4719 0.3893 0.024 Uiso 1 1 calc R U . . .
H11 H 0.1251 0.3511 0.4349 0.024 Uiso 1 1 calc R U . . .
N2 N 0.13570(12) 0.39183(15) 0.28645(10) 0.0168(3) Uani 1 1 d . . . . .
H12 H 0.088(2) 0.404(2) 0.2354(17) 0.023(5) Uiso 1 1 d . . . . .
C11 C 0.21028(16) 0.53928(19) 0.29246(14) 0.0237(3) Uani 1 1 d . . . . .
H13 H 0.2571 0.5401 0.3566 0.028 Uiso 1 1 calc R U . . .
H14 H 0.1612 0.6389 0.2892 0.028 Uiso 1 1 calc R U . . .
Mn1 Mn 0.2500 0.18166(4) 0.2500 0.00965(7) Uani 1 2 d S T P . .
Sb1 Sb -0.2500 -0.40332(2) 0.2500 0.01094(5) Uani 1 2 d S T P . .
F1 F -0.2500 -0.63268(15) 0.2500 0.0163(2) Uani 1 2 d S T P . .
F2 F -0.30474(9) -0.40184(11) 0.11651(7) 0.0228(2) Uani 1 1 d . . . . .
F3 F -0.09505(8) -0.40611(12) 0.21179(8) 0.0222(2) Uani 1 1 d . . . . .
F4 F -0.2500 -0.17305(16) 0.2500 0.0237(3) Uani 1 2 d S T P . .


_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
O1 C1 1.3330(17) . ?
O1 Mn1 1.8614(10) . ?
C1 C2 1.405(2) . ?
C1 C6 1.415(2) . ?
C2 C3 1.382(2) . ?
C2 H1 0.9500 . ?
C3 C4 1.397(2) . ?
C3 H2 0.9500 . ?
C4 C5 1.383(2) . ?
C4 H3 0.9500 . ?
C5 C6 1.408(2) . ?
C5 H4 0.9500 . ?
C6 C7 1.452(2) . ?
C7 N1 1.2838(19) . ?
C7 H5 0.9500 . ?
N1 C8 1.4740(19) . ?
N1 Mn1 2.1139(12) . ?
C8 C9 1.529(2) . ?
C8 H6 0.9900 . ?
C8 H7 0.9900 . ?
C9 C10 1.523(2) . ?
C9 H8 0.9900 . ?
C9 H9 0.9900 . ?
C10 N2 1.483(2) . ?
C10 H10 0.9900 . ?
C10 H11 0.9900 . ?
N2 C11 1.478(2) . ?
N2 Mn1 2.2350(13) . ?
N2 H12 0.86(2) . ?
C11 C11 1.506(4) 2 ?
C11 H13 0.9900 . ?
C11 H14 0.9900 . ?
Mn1 O1 1.8614(10) 2 ?
Mn1 N1 2.1139(12) 2 ?
Mn1 N2 2.2349(13) 2 ?
Sb1 F2 1.8678(10) 2_455 ?
Sb1 F2 1.8678(10) . ?
Sb1 F1 1.8718(12) . ?
Sb1 F4 1.8792(13) . ?
Sb1 F3 1.8876(10) 2_455 ?
Sb1 F3 1.8876(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
C1 O1 Mn1 122.51(9) . . ?
O1 C1 C2 118.63(13) . . ?
O1 C1 C6 122.71(13) . . ?
C2 C1 C6 118.63(13) . . ?
C3 C2 C1 120.54(14) . . ?
C3 C2 H1 119.7 . . ?
C1 C2 H1 119.7 . . ?
C2 C3 C4 121.12(14) . . ?
C2 C3 H2 119.4 . . ?
C4 C3 H2 119.4 . . ?
C5 C4 C3 119.11(14) . . ?
C5 C4 H3 120.4 . . ?
C3 C4 H3 120.4 . . ?
C4 C5 C6 120.92(14) . . ?
C4 C5 H4 119.5 . . ?
C6 C5 H4 119.5 . . ?
C5 C6 C1 119.59(14) . . ?
C5 C6 C7 119.07(13) . . ?
C1 C6 C7 121.13(13) . . ?
N1 C7 C6 124.13(13) . . ?
N1 C7 H5 117.9 . . ?
C6 C7 H5 117.9 . . ?
C7 N1 C8 118.15(13) . . ?
C7 N1 Mn1 121.70(10) . . ?
C8 N1 Mn1 119.88(9) . . ?
N1 C8 C9 110.88(13) . . ?
N1 C8 H6 109.5 . . ?
C9 C8 H6 109.5 . . ?
N1 C8 H7 109.5 . . ?
C9 C8 H7 109.5 . . ?
H6 C8 H7 108.1 . . ?
C10 C9 C8 116.05(13) . . ?
C10 C9 H8 108.3 . . ?
C8 C9 H8 108.3 . . ?
C10 C9 H9 108.3 . . ?
C8 C9 H9 108.3 . . ?
H8 C9 H9 107.4 . . ?
N2 C10 C9 112.32(13) . . ?
N2 C10 H10 109.1 . . ?
C9 C10 H10 109.1 . . ?
N2 C10 H11 109.1 . . ?
C9 C10 H11 109.1 . . ?
H10 C10 H11 107.9 . . ?
C11 N2 C10 112.18(13) . . ?
C11 N2 Mn1 106.76(10) . . ?
C10 N2 Mn1 115.21(9) . . ?
C11 N2 H12 107.1(14) . . ?
C10 N2 H12 109.6(15) . . ?
Mn1 N2 H12 105.5(14) . . ?
N2 C11 C11 109.65(12) . 2 ?
N2 C11 H13 109.7 . . ?
C11 C11 H13 109.7 2 . ?
N2 C11 H14 109.7 . . ?
C11 C11 H14 109.7 2 . ?
H13 C11 H14 108.2 . . ?
O1 Mn1 O1 179.88(6) . 2 ?
O1 Mn1 N1 86.91(5) . . ?
O1 Mn1 N1 93.02(5) 2 . ?
O1 Mn1 N1 93.02(5) . 2 ?
O1 Mn1 N1 86.91(5) 2 2 ?
N1 Mn1 N1 111.23(7) . 2 ?
O1 Mn1 N2 86.06(5) . 2 ?
O1 Mn1 N2 94.03(5) 2 2 ?
N1 Mn1 N2 162.66(5) . 2 ?
N1 Mn1 N2 84.97(5) 2 2 ?
O1 Mn1 N2 94.03(5) . . ?
O1 Mn1 N2 86.06(5) 2 . ?
N1 Mn1 N2 84.96(5) . . ?
N1 Mn1 N2 162.66(5) 2 . ?
N2 Mn1 N2 79.75(7) 2 . ?
F2 Sb1 F2 179.26(6) 2_455 . ?
F2 Sb1 F1 90.37(3) 2_455 . ?
F2 Sb1 F1 90.37(3) . . ?
F2 Sb1 F4 89.63(3) 2_455 . ?
F2 Sb1 F4 89.63(3) . . ?
F1 Sb1 F4 180.0 . . ?
F2 Sb1 F3 90.48(5) 2_455 2_455 ?
F2 Sb1 F3 89.53(5) . 2_455 ?
F1 Sb1 F3 89.31(3) . 2_455 ?
F4 Sb1 F3 90.69(3) . 2_455 ?
F2 Sb1 F3 89.53(5) 2_455 . ?
F2 Sb1 F3 90.48(5) . . ?
F1 Sb1 F3 89.31(3) . . ?
F4 Sb1 F3 90.69(3) . . ?
F3 Sb1 F3 178.62(6) 2_455 . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H12 F3 0.86(2) 2.62(2) 3.2369(16) 129.3(18) 1_565

_refine_diff_density_max         0.448
_refine_diff_density_min         -0.733
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_2_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1544516'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2017-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H28 As F6 Mn N4 O2'
_chemical_formula_weight         624.34

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
As As 0.0499 2.0058 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   8.2858(6)
_cell_length_b                   17.2042(12)
_cell_length_c                   17.7305(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2527.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(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_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    1.893
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.718
_exptl_absorpt_correction_T_max  0.812
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20245
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.297
_diffrn_reflns_theta_max         28.413
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6300
_reflns_number_gt                5776
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.997

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0416P)²+4.3826P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2384 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_chemical_absolute_configuration .
_refine_ls_number_reflns         6300
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0954
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0086(4) 0.4674(2) 0.10283(17) 0.0205(7) Uani 1 1 d . . . . .
C1 C -0.0802(6) 0.4040(3) 0.0770(3) 0.0208(9) Uani 1 1 d . . . . .
C2 C -0.1576(7) 0.3534(3) 0.1278(3) 0.0276(11) Uani 1 1 d . . . . .
H1 H -0.1554 0.3652 0.1801 0.033 Uiso 1 1 calc R U . . .
C3 C -0.2361(7) 0.2877(3) 0.1041(3) 0.0295(11) Uani 1 1 d . . . . .
H2 H -0.2873 0.2549 0.1400 0.035 Uiso 1 1 calc R U . . .
C4 C -0.2416(6) 0.2682(3) 0.0269(3) 0.0256(10) Uani 1 1 d . . . . .
H3 H -0.2937 0.2220 0.0105 0.031 Uiso 1 1 calc R U . . .
C5 C -0.1702(6) 0.3174(3) -0.0242(3) 0.0225(9) Uani 1 1 d . . . . .
H4 H -0.1755 0.3054 -0.0764 0.027 Uiso 1 1 calc R U . . .
C6 C -0.0892(6) 0.3853(3) -0.0009(3) 0.0186(9) Uani 1 1 d . . . . .
C7 C -0.0416(5) 0.4422(3) -0.0571(3) 0.0191(9) Uani 1 1 d . . . . .
H5 H -0.0771 0.4341 -0.1075 0.023 Uiso 1 1 calc R U . . .
N1 N 0.0449(5) 0.5026(2) -0.0440(2) 0.0172(7) Uani 1 1 d . . . . .
C8 C 0.0363(6) 0.5657(3) -0.1006(3) 0.0205(9) Uani 1 1 d . . . . .
H6 H -0.0118 0.5456 -0.1478 0.025 Uiso 1 1 calc R U . . .
H7 H 0.1463 0.5848 -0.1120 0.025 Uiso 1 1 calc R U . . .
C9 C -0.0667(6) 0.6322(3) -0.0699(3) 0.0216(9) Uani 1 1 d . . . . .
H8 H -0.0879 0.6695 -0.1112 0.026 Uiso 1 1 calc R U . . .
H9 H -0.1720 0.6109 -0.0533 0.026 Uiso 1 1 calc R U . . .
C10 C 0.0095(6) 0.6757(3) -0.0042(3) 0.0223(9) Uani 1 1 d . . . . .
H10 H 0.1172 0.6949 -0.0196 0.027 Uiso 1 1 calc R U . . .
H11 H -0.0580 0.7214 0.0083 0.027 Uiso 1 1 calc R U . . .
N2 N 0.0270(5) 0.6262(2) 0.0640(2) 0.0166(7) Uani 1 1 d . . . . .
H12 H -0.0845 0.6118 0.0805 0.020 Uiso 1 1 calc R U . . .
C11 C 0.1017(6) 0.6708(2) 0.1277(2) 0.0188(9) Uani 1 1 d . . . . .
H13 H 0.0256 0.7109 0.1461 0.023 Uiso 1 1 calc R U . . .
H14 H 0.2013 0.6971 0.1102 0.023 Uiso 1 1 calc R U . . .
C12 C 0.1411(6) 0.6144(3) 0.1901(2) 0.0194(8) Uani 1 1 d . . . . .
H15 H 0.1989 0.6417 0.2312 0.023 Uiso 1 1 calc R U . . .
H16 H 0.0404 0.5923 0.2111 0.023 Uiso 1 1 calc R U . . .
N3 N 0.2441(5) 0.5513(2) 0.1591(2) 0.0166(7) Uani 1 1 d . . . . .
H17 H 0.340(7) 0.568(3) 0.153(3) 0.014(12) Uiso 1 1 d . . . . .
C13 C 0.2611(6) 0.4873(3) 0.2140(3) 0.0198(9) Uani 1 1 d . . . . .
H18 H 0.1535 0.4644 0.2239 0.024 Uiso 1 1 calc R U . . .
H19 H 0.3024 0.5085 0.2622 0.024 Uiso 1 1 calc R U . . .
C14 C 0.3747(7) 0.4236(3) 0.1866(3) 0.0242(10) Uani 1 1 d . . . . .
H20 H 0.3926 0.3862 0.2281 0.029 Uiso 1 1 calc R U . . .
H21 H 0.4802 0.4473 0.1739 0.029 Uiso 1 1 calc R U . . .
C15 C 0.3114(6) 0.3796(3) 0.1174(3) 0.0233(10) Uani 1 1 d . . . . .
H22 H 0.3830 0.3349 0.1063 0.028 Uiso 1 1 calc R U . . .
H23 H 0.2019 0.3592 0.1279 0.028 Uiso 1 1 calc R U . . .
N4 N 0.3061(5) 0.4326(2) 0.0514(2) 0.0195(8) Uani 1 1 d . . . . .
O2 O 0.3171(4) 0.58324(18) 0.00755(17) 0.0171(6) Uani 1 1 d . . . . .
Mn1 Mn 0.15523(8) 0.52355(4) 0.05376(3) 0.01416(14) Uani 1 1 d . . . . .
As1 As 0.62989(6) 0.68503(3) 0.21423(3) 0.01980(12) Uani 1 1 d . . . . .
F1 F 0.5104(7) 0.7486(3) 0.2600(4) 0.106(3) Uani 1 1 d . . . . .
F2 F 0.7233(5) 0.7600(2) 0.1686(2) 0.0495(11) Uani 1 1 d . . . . .
F3 F 0.4895(5) 0.6788(3) 0.1440(2) 0.0609(13) Uani 1 1 d . . . . .
F4 F 0.7455(6) 0.6193(3) 0.1682(3) 0.0764(17) Uani 1 1 d . . . . .
F5 F 0.5347(5) 0.6093(2) 0.2592(2) 0.0441(9) Uani 1 1 d . . . . .
F6 F 0.7720(6) 0.6894(4) 0.2827(3) 0.090(2) Uani 1 1 d . . . . .
C16 C 0.4167(6) 0.4233(3) 0.0011(3) 0.0221(9) Uani 1 1 d . . . . .
H24 H 0.4771 0.3763 0.0022 0.027 Uiso 1 1 calc R U . . .
C17 C 0.4553(5) 0.4794(3) -0.0570(3) 0.0195(8) Uani 1 1 d . . . . .
C18 C 0.5543(6) 0.4576(3) -0.1180(3) 0.0237(10) Uani 1 1 d . . . . .
H25 H 0.5841 0.4046 -0.1237 0.028 Uiso 1 1 calc R U . . .
C19 C 0.6089(6) 0.5113(3) -0.1693(3) 0.0250(10) Uani 1 1 d . . . . .
H26 H 0.6738 0.4955 -0.2107 0.030 Uiso 1 1 calc R U . . .
C20 C 0.5676(6) 0.5893(3) -0.1598(3) 0.0241(10) Uani 1 1 d . . . . .
H27 H 0.6065 0.6269 -0.1946 0.029 Uiso 1 1 calc R U . . .
C21 C 0.4706(6) 0.6126(3) -0.1002(3) 0.0205(9) Uani 1 1 d . . . . .
H28 H 0.4443 0.6660 -0.0945 0.025 Uiso 1 1 calc R U . . .
C22 C 0.4107(5) 0.5583(3) -0.0482(3) 0.0174(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
O1 C1 1.323(6) . ?
O1 Mn1 1.880(3) . ?
C1 C2 1.407(6) . ?
C1 C6 1.420(6) . ?
C2 C3 1.371(7) . ?
C2 H1 0.9500 . ?
C3 C4 1.410(8) . ?
C3 H2 0.9500 . ?
C4 C5 1.373(7) . ?
C4 H3 0.9500 . ?
C5 C6 1.409(7) . ?
C5 H4 0.9500 . ?
C6 C7 1.451(6) . ?
C7 N1 1.284(6) . ?
C7 H5 0.9500 . ?
N1 C8 1.479(6) . ?
N1 Mn1 1.992(4) . ?
C8 C9 1.528(7) . ?
C8 H6 0.9900 . ?
C8 H7 0.9900 . ?
C9 C10 1.522(6) . ?
C9 H8 0.9900 . ?
C9 H9 0.9900 . ?
C10 N2 1.487(6) . ?
C10 H10 0.9900 . ?
C10 H11 0.9900 . ?
N2 C11 1.498(5) . ?
N2 Mn1 2.068(4) . ?
N2 H12 1.0000 . ?
C11 C12 1.508(6) . ?
C11 H13 0.9900 . ?
C11 H14 0.9900 . ?
C12 N3 1.488(6) . ?
C12 H15 0.9900 . ?
C12 H16 0.9900 . ?
N3 C13 1.477(6) . ?
N3 Mn1 2.063(4) . ?
N3 H17 0.85(6) . ?
C13 C14 1.524(7) . ?
C13 H18 0.9900 . ?
C13 H19 0.9900 . ?
C14 C15 1.534(6) . ?
C14 H20 0.9900 . ?
C14 H21 0.9900 . ?
C15 N4 1.485(6) . ?
C15 H22 0.9900 . ?
C15 H23 0.9900 . ?
N4 C16 1.289(6) . ?
N4 Mn1 2.003(4) . ?
O2 C22 1.327(5) . ?
O2 Mn1 1.878(3) . ?
As1 F1 1.683(4) . ?
As1 F4 1.692(4) . ?
As1 F6 1.693(4) . ?
As1 F3 1.707(3) . ?
As1 F2 1.708(3) . ?
As1 F5 1.720(3) . ?
C16 C17 1.448(6) . ?
C16 H24 0.9500 . ?
C17 C18 1.408(6) . ?
C17 C22 1.416(6) . ?
C18 C19 1.373(7) . ?
C18 H25 0.9500 . ?
C19 C20 1.395(8) . ?
C19 H26 0.9500 . ?
C20 C21 1.387(7) . ?
C20 H27 0.9500 . ?
C21 C22 1.403(6) . ?
C21 H28 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 Mn1 126.0(3) . . ?
O1 C1 C2 119.5(4) . . ?
O1 C1 C6 123.1(4) . . ?
C2 C1 C6 117.3(4) . . ?
C3 C2 C1 122.0(5) . . ?
C3 C2 H1 119.0 . . ?
C1 C2 H1 119.0 . . ?
C2 C3 C4 120.6(5) . . ?
C2 C3 H2 119.7 . . ?
C4 C3 H2 119.7 . . ?
C5 C4 C3 118.7(5) . . ?
C5 C4 H3 120.7 . . ?
C3 C4 H3 120.7 . . ?
C4 C5 C6 121.6(4) . . ?
C4 C5 H4 119.2 . . ?
C6 C5 H4 119.2 . . ?
C5 C6 C1 119.8(4) . . ?
C5 C6 C7 119.2(4) . . ?
C1 C6 C7 120.1(4) . . ?
N1 C7 C6 124.9(4) . . ?
N1 C7 H5 117.5 . . ?
C6 C7 H5 117.5 . . ?
C7 N1 C8 116.3(4) . . ?
C7 N1 Mn1 124.1(3) . . ?
C8 N1 Mn1 118.7(3) . . ?
N1 C8 C9 109.6(4) . . ?
N1 C8 H6 109.8 . . ?
C9 C8 H6 109.8 . . ?
N1 C8 H7 109.8 . . ?
C9 C8 H7 109.8 . . ?
H6 C8 H7 108.2 . . ?
C10 C9 C8 114.2(4) . . ?
C10 C9 H8 108.7 . . ?
C8 C9 H8 108.7 . . ?
C10 C9 H9 108.7 . . ?
C8 C9 H9 108.7 . . ?
H8 C9 H9 107.6 . . ?
N2 C10 C9 112.4(4) . . ?
N2 C10 H10 109.1 . . ?
C9 C10 H10 109.1 . . ?
N2 C10 H11 109.1 . . ?
C9 C10 H11 109.1 . . ?
H10 C10 H11 107.9 . . ?
C10 N2 C11 111.0(3) . . ?
C10 N2 Mn1 117.9(3) . . ?
C11 N2 Mn1 107.0(3) . . ?
C10 N2 H12 106.8 . . ?
C11 N2 H12 106.8 . . ?
Mn1 N2 H12 106.8 . . ?
N2 C11 C12 108.2(3) . . ?
N2 C11 H13 110.1 . . ?
C12 C11 H13 110.1 . . ?
N2 C11 H14 110.1 . . ?
C12 C11 H14 110.1 . . ?
H13 C11 H14 108.4 . . ?
N3 C12 C11 108.7(3) . . ?
N3 C12 H15 109.9 . . ?
C11 C12 H15 109.9 . . ?
N3 C12 H16 109.9 . . ?
C11 C12 H16 109.9 . . ?
H15 C12 H16 108.3 . . ?
C13 N3 C12 110.8(3) . . ?
C13 N3 Mn1 117.3(3) . . ?
C12 N3 Mn1 107.4(3) . . ?
C13 N3 H17 105(4) . . ?
C12 N3 H17 110(4) . . ?
Mn1 N3 H17 107(3) . . ?
N3 C13 C14 112.6(4) . . ?
N3 C13 H18 109.1 . . ?
C14 C13 H18 109.1 . . ?
N3 C13 H19 109.1 . . ?
C14 C13 H19 109.1 . . ?
H18 C13 H19 107.8 . . ?
C13 C14 C15 113.5(4) . . ?
C13 C14 H20 108.9 . . ?
C15 C14 H20 108.9 . . ?
C13 C14 H21 108.9 . . ?
C15 C14 H21 108.9 . . ?
H20 C14 H21 107.7 . . ?
N4 C15 C14 109.7(4) . . ?
N4 C15 H22 109.7 . . ?
C14 C15 H22 109.7 . . ?
N4 C15 H23 109.7 . . ?
C14 C15 H23 109.7 . . ?
H22 C15 H23 108.2 . . ?
C16 N4 C15 116.6(4) . . ?
C16 N4 Mn1 123.7(3) . . ?
C15 N4 Mn1 118.8(3) . . ?
C22 O2 Mn1 124.4(3) . . ?
O2 Mn1 O1 177.55(14) . . ?
O2 Mn1 N1 92.70(15) . . ?
O1 Mn1 N1 88.75(15) . . ?
O2 Mn1 N4 88.42(15) . . ?
O1 Mn1 N4 93.36(16) . . ?
N1 Mn1 N4 97.28(16) . . ?
O2 Mn1 N3 90.76(15) . . ?
O1 Mn1 N3 87.59(15) . . ?
N1 Mn1 N3 173.18(16) . . ?
N4 Mn1 N3 88.68(16) . . ?
O2 Mn1 N2 86.47(14) . . ?
O1 Mn1 N2 91.56(15) . . ?
N1 Mn1 N2 89.74(15) . . ?
N4 Mn1 N2 171.51(16) . . ?
N3 Mn1 N2 84.61(15) . . ?
F1 As1 F4 178.4(3) . . ?
F1 As1 F6 91.9(4) . . ?
F4 As1 F6 89.0(3) . . ?
F1 As1 F3 89.5(3) . . ?
F4 As1 F3 89.6(3) . . ?
F6 As1 F3 178.5(3) . . ?
F1 As1 F2 90.2(3) . . ?
F4 As1 F2 91.2(2) . . ?
F6 As1 F2 89.5(2) . . ?
F3 As1 F2 90.63(18) . . ?
F1 As1 F5 90.0(2) . . ?
F4 As1 F5 88.7(2) . . ?
F6 As1 F5 91.13(19) . . ?
F3 As1 F5 88.75(17) . . ?
F2 As1 F5 179.36(19) . . ?
N4 C16 C17 124.5(4) . . ?
N4 C16 H24 117.7 . . ?
C17 C16 H24 117.7 . . ?
C18 C17 C22 119.5(4) . . ?
C18 C17 C16 119.8(4) . . ?
C22 C17 C16 120.2(4) . . ?
C19 C18 C17 121.4(5) . . ?
C19 C18 H25 119.3 . . ?
C17 C18 H25 119.3 . . ?
C18 C19 C20 119.1(4) . . ?
C18 C19 H26 120.4 . . ?
C20 C19 H26 120.4 . . ?
C21 C20 C19 120.7(5) . . ?
C21 C20 H27 119.6 . . ?
C19 C20 H27 119.6 . . ?
C20 C21 C22 121.0(5) . . ?
C20 C21 H28 119.5 . . ?
C22 C21 H28 119.5 . . ?
O2 C22 C21 118.8(4) . . ?
O2 C22 C17 123.0(4) . . ?
C21 C22 C17 118.2(4) . . ?

_refine_diff_density_max         0.822
_refine_diff_density_min         -0.527
_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_20150823
_database_code_depnum_ccdc_archive 'CCDC 1544527'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2017-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H34 Mn N5 O6'
_chemical_formula_weight         543.50

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   8.103(2)
_cell_length_b                   19.428(6)
_cell_length_c                   16.966(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.227(6)
_cell_angle_gamma                90
_cell_volume                     2610.4(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(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_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             1144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.553
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.870
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16361
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.430
_diffrn_reflns_theta_max         28.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             6020
_reflns_number_gt                5149
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+4.6315P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6020
_refine_ls_number_parameters     338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0698
_refine_ls_wR_factor_ref         0.1622
_refine_ls_wR_factor_gt          0.1554
_refine_ls_goodness_of_fit_ref   1.263
_refine_ls_restrained_S_all      1.263
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.1630(3) 0.15093(12) -0.05833(14) 0.0400(5) Uani 1 1 d . . . . .
C1 C -0.2714(4) 0.15944(19) -0.1280(2) 0.0400(7) Uani 1 1 d . . . . .
C2 C -0.3361(5) 0.1010(2) -0.1721(3) 0.0583(11) Uani 1 1 d . . . . .
H1 H -0.3028 0.0574 -0.1524 0.070 Uiso 1 1 calc R U . . .
C3 C -0.4499(6) 0.1081(3) -0.2451(3) 0.0700(14) Uani 1 1 d . . . . .
H2 H -0.4921 0.0689 -0.2738 0.084 Uiso 1 1 calc R U . . .
C4 C -0.5020(5) 0.1720(3) -0.2763(2) 0.0650(13) Uani 1 1 d . . . . .
H3 H -0.5766 0.1760 -0.3259 0.078 Uiso 1 1 calc R U . . .
C5 C -0.4424(5) 0.2291(3) -0.2332(2) 0.0543(10) Uani 1 1 d . . . . .
H4 H -0.4788 0.2723 -0.2534 0.065 Uiso 1 1 calc R U . . .
C6 C -0.3276(4) 0.22438(19) -0.1591(2) 0.0386(7) Uani 1 1 d . . . . .
C7 C -0.2910(4) 0.28589(19) -0.1114(2) 0.0404(7) Uani 1 1 d . . . . .
H5 H -0.3550 0.3249 -0.1288 0.048 Uiso 1 1 calc R U . . .
N1 N -0.1779(3) 0.29089(14) -0.04732(16) 0.0344(6) Uani 1 1 d . . . . .
C8 C -0.1870(5) 0.35061(18) 0.0060(2) 0.0445(8) Uani 1 1 d . . . . .
H6 H -0.2682 0.3837 -0.0221 0.053 Uiso 1 1 calc R U . . .
H7 H -0.0776 0.3730 0.0198 0.053 Uiso 1 1 calc R U . . .
C9 C -0.2392(5) 0.3271(2) 0.0821(3) 0.0544(10) Uani 1 1 d . . . . .
H8 H -0.2649 0.3674 0.1110 0.065 Uiso 1 1 calc R U . . .
H9 H -0.3424 0.3004 0.0670 0.065 Uiso 1 1 calc R U . . .
C10 C -0.1105(5) 0.2843(2) 0.1388(2) 0.0531(10) Uani 1 1 d . . . . .
H10 H -0.0039 0.3088 0.1506 0.064 Uiso 1 1 calc R U . . .
H11 H -0.1476 0.2782 0.1891 0.064 Uiso 1 1 calc R U . . .
N2 N -0.0842(4) 0.21580(16) 0.10501(18) 0.0431(7) Uani 1 1 d . . . . .
H12 H -0.190(6) 0.190(2) 0.095(3) 0.061(13) Uiso 1 1 d . . . . .
C11 C 0.0415(5) 0.1742(2) 0.1600(2) 0.0522(10) Uani 1 1 d . . . . .
H13 H -0.0019 0.1614 0.2070 0.063 Uiso 1 1 calc R U . . .
H14 H 0.1441 0.2006 0.1779 0.063 Uiso 1 1 calc R U . . .
C12 C 0.0789(5) 0.1105(2) 0.1163(3) 0.0558(10) Uani 1 1 d . . . . .
H15 H 0.1589 0.0818 0.1524 0.067 Uiso 1 1 calc R U . . .
H16 H -0.0240 0.0843 0.0980 0.067 Uiso 1 1 calc R U . . .
N3 N 0.1499(4) 0.13102(16) 0.04651(19) 0.0436(7) Uani 1 1 d . . . . .
H17 H 0.252(5) 0.145(2) 0.072(2) 0.045(11) Uiso 1 1 d . . . . .
C13 C 0.1704(6) 0.0714(2) -0.0049(3) 0.0617(11) Uani 1 1 d . . . . .
H18 H 0.0600 0.0519 -0.0268 0.074 Uiso 1 1 calc R U . . .
H19 H 0.2368 0.0364 0.0284 0.074 Uiso 1 1 calc R U . . .
C14 C 0.2545(6) 0.0890(2) -0.0735(3) 0.0637(12) Uani 1 1 d . . . . .
H20 H 0.2783 0.0466 -0.0992 0.076 Uiso 1 1 calc R U . . .
H21 H 0.3617 0.1111 -0.0516 0.076 Uiso 1 1 calc R U . . .
C15 C 0.1519(6) 0.1356(2) -0.1371(3) 0.0533(10) Uani 1 1 d . . . . .
H22 H 0.2068 0.1395 -0.1824 0.064 Uiso 1 1 calc R U . . .
H23 H 0.0406 0.1160 -0.1564 0.064 Uiso 1 1 calc R U . . .
N4 N 0.1357(4) 0.20426(15) -0.10281(17) 0.0402(6) Uani 1 1 d . . . . .
C16 C 0.2215(4) 0.25332(19) -0.1246(2) 0.0403(7) Uani 1 1 d . . . . .
H24 H 0.2728 0.2454 -0.1679 0.048 Uiso 1 1 calc R U . . .
C17 C 0.2442(4) 0.32018(17) -0.08669(19) 0.0338(6) Uani 1 1 d . . . . .
C18 C 0.3102(4) 0.3738(2) -0.1264(2) 0.0444(8) Uani 1 1 d . . . . .
H25 H 0.3296 0.3664 -0.1778 0.053 Uiso 1 1 calc R U . . .
C19 C 0.3462(5) 0.4366(2) -0.0905(3) 0.0539(10) Uani 1 1 d . . . . .
H26 H 0.3881 0.4720 -0.1176 0.065 Uiso 1 1 calc R U . . .
C20 C 0.3199(5) 0.44701(19) -0.0137(3) 0.0492(9) Uani 1 1 d . . . . .
H27 H 0.3442 0.4897 0.0109 0.059 Uiso 1 1 calc R U . . .
C21 C 0.2581(4) 0.39518(17) 0.0272(2) 0.0388(7) Uani 1 1 d . . . . .
H28 H 0.2426 0.4032 0.0792 0.047 Uiso 1 1 calc R U . . .
C22 C 0.2181(3) 0.33043(16) -0.00838(18) 0.0296(6) Uani 1 1 d . . . . .
O2 O 0.1614(3) 0.28171(11) 0.03413(12) 0.0325(5) Uani 1 1 d . . . . .
Mn1 Mn -0.00078(6) 0.21579(2) -0.01050(3) 0.03012(14) Uani 1 1 d . . . . .
N5 N 0.5722(5) 0.3833(2) 0.6554(3) 0.0636(10) Uani 1 1 d . . . . .
O3 O 0.7151(5) 0.4004(4) 0.6753(4) 0.159(3) Uani 1 1 d . . . . .
O4 O 0.5326(5) 0.3416(2) 0.6005(2) 0.0892(12) Uani 1 1 d . . . . .
O5 O 0.4703(5) 0.4031(3) 0.6937(3) 0.1082(15) Uani 1 1 d . . . . .
C23 C 0.9534(8) 0.5151(3) 0.7967(3) 0.0812(15) Uani 1 1 d . . . . .
H29 H 0.9124 0.5026 0.7413 0.122 Uiso 1 1 calc R U . . .
H30 H 1.0746 0.5149 0.8087 0.122 Uiso 1 1 calc R U . . .
H31 H 0.9135 0.5603 0.8059 0.122 Uiso 1 1 calc R U . . .
C24 C 0.8908(6) 0.4647(3) 0.8498(3) 0.0695(13) Uani 1 1 d . . . . .
H32 H 0.9271 0.4189 0.8383 0.083 Uiso 1 1 calc R U . . .
H33 H 0.9415 0.4752 0.9056 0.083 Uiso 1 1 calc R U . . .
O6 O 0.7147(5) 0.4650(2) 0.8401(2) 0.0731(10) Uani 1 1 d . . . . .
H34 H 0.672(7) 0.452(3) 0.798(3) 0.08(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
O1 C1 1.325(4) . ?
O1 Mn1 1.877(2) . ?
C1 C2 1.399(5) . ?
C1 C6 1.406(5) . ?
C2 C3 1.386(7) . ?
C2 H1 0.9300 . ?
C3 C4 1.380(7) . ?
C3 H2 0.9300 . ?
C4 C5 1.359(6) . ?
C4 H3 0.9300 . ?
C5 C6 1.400(5) . ?
C5 H4 0.9300 . ?
C6 C7 1.439(5) . ?
C7 N1 1.268(4) . ?
C7 H5 0.9300 . ?
N1 C8 1.483(4) . ?
N1 Mn1 2.049(3) . ?
C8 C9 1.513(5) . ?
C8 H6 0.9700 . ?
C8 H7 0.9700 . ?
C9 C10 1.509(6) . ?
C9 H8 0.9700 . ?
C9 H9 0.9700 . ?
C10 N2 1.482(5) . ?
C10 H10 0.9700 . ?
C10 H11 0.9700 . ?
N2 C11 1.469(5) . ?
N2 Mn1 2.204(3) . ?
N2 H12 0.98(5) . ?
C11 C12 1.506(6) . ?
C11 H13 0.9700 . ?
C11 H14 0.9700 . ?
C12 N3 1.477(5) . ?
C12 H15 0.9700 . ?
C12 H16 0.9700 . ?
N3 C13 1.480(5) . ?
N3 Mn1 2.154(3) . ?
N3 H17 0.89(4) . ?
C13 C14 1.508(7) . ?
C13 H18 0.9700 . ?
C13 H19 0.9700 . ?
C14 C15 1.516(6) . ?
C14 H20 0.9700 . ?
C14 H21 0.9700 . ?
C15 N4 1.472(4) . ?
C15 H22 0.9700 . ?
C15 H23 0.9700 . ?
N4 C16 1.279(4) . ?
N4 Mn1 2.112(3) . ?
C16 C17 1.444(5) . ?
C16 H24 0.9300 . ?
C17 C22 1.403(4) . ?
C17 C18 1.406(4) . ?
C18 C19 1.369(6) . ?
C18 H25 0.9300 . ?
C19 C20 1.379(6) . ?
C19 H26 0.9300 . ?
C20 C21 1.375(5) . ?
C20 H27 0.9300 . ?
C21 C22 1.403(4) . ?
C21 H28 0.9300 . ?
C22 O2 1.329(3) . ?
O2 Mn1 1.876(2) . ?
N5 O3 1.183(5) . ?
N5 O5 1.216(5) . ?
N5 O4 1.225(5) . ?
C23 C24 1.490(7) . ?
C23 H29 0.9600 . ?
C23 H30 0.9600 . ?
C23 H31 0.9600 . ?
C24 O6 1.401(6) . ?
C24 H32 0.9700 . ?
C24 H33 0.9700 . ?
O6 H34 0.76(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 Mn1 125.0(2) . . ?
O1 C1 C2 118.6(4) . . ?
O1 C1 C6 123.2(3) . . ?
C2 C1 C6 118.2(3) . . ?
C3 C2 C1 120.1(5) . . ?
C3 C2 H1 120.0 . . ?
C1 C2 H1 120.0 . . ?
C4 C3 C2 121.5(4) . . ?
C4 C3 H2 119.2 . . ?
C2 C3 H2 119.2 . . ?
C5 C4 C3 118.9(4) . . ?
C5 C4 H3 120.5 . . ?
C3 C4 H3 120.5 . . ?
C4 C5 C6 121.4(4) . . ?
C4 C5 H4 119.3 . . ?
C6 C5 H4 119.3 . . ?
C5 C6 C1 119.8(4) . . ?
C5 C6 C7 118.0(4) . . ?
C1 C6 C7 121.5(3) . . ?
N1 C7 C6 124.8(3) . . ?
N1 C7 H5 117.6 . . ?
C6 C7 H5 117.6 . . ?
C7 N1 C8 117.5(3) . . ?
C7 N1 Mn1 122.6(2) . . ?
C8 N1 Mn1 119.6(2) . . ?
N1 C8 C9 110.1(3) . . ?
N1 C8 H6 109.6 . . ?
C9 C8 H6 109.6 . . ?
N1 C8 H7 109.6 . . ?
C9 C8 H7 109.6 . . ?
H6 C8 H7 108.2 . . ?
C10 C9 C8 115.4(3) . . ?
C10 C9 H8 108.4 . . ?
C8 C9 H8 108.4 . . ?
C10 C9 H9 108.4 . . ?
C8 C9 H9 108.4 . . ?
H8 C9 H9 107.5 . . ?
N2 C10 C9 112.6(3) . . ?
N2 C10 H10 109.1 . . ?
C9 C10 H10 109.1 . . ?
N2 C10 H11 109.1 . . ?
C9 C10 H11 109.1 . . ?
H10 C10 H11 107.8 . . ?
C11 N2 C10 112.7(3) . . ?
C11 N2 Mn1 105.2(2) . . ?
C10 N2 Mn1 116.1(2) . . ?
C11 N2 H12 107(3) . . ?
C10 N2 H12 110(3) . . ?
Mn1 N2 H12 106(3) . . ?
N2 C11 C12 108.9(3) . . ?
N2 C11 H13 109.9 . . ?
C12 C11 H13 109.9 . . ?
N2 C11 H14 109.9 . . ?
C12 C11 H14 109.9 . . ?
H13 C11 H14 108.3 . . ?
N3 C12 C11 109.1(3) . . ?
N3 C12 H15 109.9 . . ?
C11 C12 H15 109.9 . . ?
N3 C12 H16 109.9 . . ?
C11 C12 H16 109.9 . . ?
H15 C12 H16 108.3 . . ?
C12 N3 C13 111.9(3) . . ?
C12 N3 Mn1 106.6(2) . . ?
C13 N3 Mn1 117.2(3) . . ?
C12 N3 H17 100(3) . . ?
C13 N3 H17 108(3) . . ?
Mn1 N3 H17 112(3) . . ?
N3 C13 C14 113.7(3) . . ?
N3 C13 H18 108.8 . . ?
C14 C13 H18 108.8 . . ?
N3 C13 H19 108.8 . . ?
C14 C13 H19 108.8 . . ?
H18 C13 H19 107.7 . . ?
C13 C14 C15 114.5(4) . . ?
C13 C14 H20 108.6 . . ?
C15 C14 H20 108.6 . . ?
C13 C14 H21 108.6 . . ?
C15 C14 H21 108.6 . . ?
H20 C14 H21 107.6 . . ?
N4 C15 C14 110.0(3) . . ?
N4 C15 H22 109.7 . . ?
C14 C15 H22 109.7 . . ?
N4 C15 H23 109.7 . . ?
C14 C15 H23 109.7 . . ?
H22 C15 H23 108.2 . . ?
C16 N4 C15 117.5(3) . . ?
C16 N4 Mn1 122.5(2) . . ?
C15 N4 Mn1 119.6(2) . . ?
N4 C16 C17 124.5(3) . . ?
N4 C16 H24 117.7 . . ?
C17 C16 H24 117.7 . . ?
C22 C17 C18 119.8(3) . . ?
C22 C17 C16 121.3(3) . . ?
C18 C17 C16 118.6(3) . . ?
C19 C18 C17 121.0(4) . . ?
C19 C18 H25 119.5 . . ?
C17 C18 H25 119.5 . . ?
C18 C19 C20 119.4(3) . . ?
C18 C19 H26 120.3 . . ?
C20 C19 H26 120.3 . . ?
C21 C20 C19 121.0(3) . . ?
C21 C20 H27 119.5 . . ?
C19 C20 H27 119.5 . . ?
C20 C21 C22 121.0(3) . . ?
C20 C21 H28 119.5 . . ?
C22 C21 H28 119.5 . . ?
O2 C22 C17 123.5(3) . . ?
O2 C22 C21 118.7(3) . . ?
C17 C22 C21 117.8(3) . . ?
C22 O2 Mn1 124.07(18) . . ?
O2 Mn1 O1 178.22(10) . . ?
O2 Mn1 N1 91.29(10) . . ?
O1 Mn1 N1 88.00(11) . . ?
O2 Mn1 N4 86.53(10) . . ?
O1 Mn1 N4 92.12(11) . . ?
N1 Mn1 N4 107.00(11) . . ?
O2 Mn1 N3 93.36(11) . . ?
O1 Mn1 N3 87.67(11) . . ?
N1 Mn1 N3 167.23(11) . . ?
N4 Mn1 N3 85.17(12) . . ?
O2 Mn1 N2 87.80(10) . . ?
O1 Mn1 N2 93.78(11) . . ?
N1 Mn1 N2 86.80(11) . . ?
N4 Mn1 N2 165.18(12) . . ?
N3 Mn1 N2 81.50(12) . . ?
O3 N5 O5 119.6(5) . . ?
O3 N5 O4 119.1(5) . . ?
O5 N5 O4 121.1(4) . . ?
C24 C23 H29 109.5 . . ?
C24 C23 H30 109.5 . . ?
H29 C23 H30 109.5 . . ?
C24 C23 H31 109.5 . . ?
H29 C23 H31 109.5 . . ?
H30 C23 H31 109.5 . . ?
O6 C24 C23 113.3(4) . . ?
O6 C24 H32 108.9 . . ?
C23 C24 H32 108.9 . . ?
O6 C24 H33 108.9 . . ?
C23 C24 H33 108.9 . . ?
H32 C24 H33 107.7 . . ?
C24 O6 H34 111(5) . . ?

_refine_diff_density_max         0.548
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_PCCN
_database_code_depnum_ccdc_archive 'CCDC 1544529'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2017-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H28 Cl Mn N4 O2'
_chemical_formula_weight         470.87

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

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

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

_cell_length_a                   7.755(2)
_cell_length_b                   16.035(4)
_cell_length_c                   17.360(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2158.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(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_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.762
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_T_max  0.913
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12497
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.145
_diffrn_reflns_theta_max         28.402
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_point_group_measured_fraction_full 0.960
_reflns_number_total             2507
_reflns_number_gt                2126
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0219P)²+3.2399P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2507
_refine_ls_number_parameters     141
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.1228
_refine_ls_wR_factor_gt          0.1164
_refine_ls_goodness_of_fit_ref   1.243
_refine_ls_restrained_S_all      1.243
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3515(3) 0.35585(12) 0.46038(11) 0.0360(5) Uani 1 1 d . . . . .
C1 C 0.4161(4) 0.39619(18) 0.40060(16) 0.0324(6) Uani 1 1 d . . . . .
C2 C 0.4141(4) 0.48326(19) 0.4004(2) 0.0433(7) Uani 1 1 d . . . . .
H1 H 0.3655 0.5116 0.4418 0.052 Uiso 1 1 calc R U . . .
C3 C 0.4822(5) 0.5276(2) 0.3404(2) 0.0501(9) Uani 1 1 d . . . . .
H2 H 0.4753 0.5855 0.3406 0.060 Uiso 1 1 calc R U . . .
C4 C 0.5612(5) 0.4874(2) 0.2797(2) 0.0532(9) Uani 1 1 d . . . . .
H3 H 0.6106 0.5180 0.2399 0.064 Uiso 1 1 calc R U . . .
C5 C 0.5661(5) 0.4024(2) 0.27850(17) 0.0463(8) Uani 1 1 d . . . . .
H4 H 0.6200 0.3753 0.2377 0.056 Uiso 1 1 calc R U . . .
C6 C 0.4915(4) 0.35496(19) 0.33759(16) 0.0342(6) Uani 1 1 d . . . . .
C7 C 0.5130(4) 0.26588(19) 0.33738(16) 0.0374(7) Uani 1 1 d . . . . .
H5 H 0.5870 0.2431 0.3009 0.045 Uiso 1 1 calc R U . . .
N1 N 0.4375(3) 0.21552(15) 0.38397(14) 0.0358(6) Uani 1 1 d . . . . .
Mn1 Mn 0.2500 0.2500 0.45837(3) 0.02904(17) Uani 1 2 d S T P . .
C8 C 0.5085(5) 0.13086(19) 0.38989(19) 0.0439(8) Uani 1 1 d . . . . .
H7 H 0.5886 0.1211 0.3479 0.053 Uiso 1 1 calc R U . . .
H6 H 0.4161 0.0903 0.3860 0.053 Uiso 1 1 calc R U . . .
C9 C 0.6009(5) 0.1207(2) 0.4663(2) 0.0504(9) Uani 1 1 d . . . . .
H8 H 0.6616 0.0678 0.4658 0.060 Uiso 1 1 calc R U . . .
H9 H 0.6865 0.1645 0.4708 0.060 Uiso 1 1 calc R U . . .
C10 C 0.4867(5) 0.1234(2) 0.5366(2) 0.0494(9) Uani 1 1 d . . . . .
H11 H 0.3964 0.0819 0.5313 0.059 Uiso 1 1 calc R U . . .
H10 H 0.5545 0.1092 0.5817 0.059 Uiso 1 1 calc R U . . .
N2 N 0.4071(4) 0.20622(16) 0.54798(15) 0.0381(6) Uani 1 1 d . . . . .
H12 H 0.488(5) 0.242(2) 0.5544(19) 0.047(10) Uiso 1 1 d . . . . .
C11 C 0.3007(5) 0.2097(2) 0.61787(18) 0.0525(9) Uani 1 1 d . . . . .
H13 H 0.3738 0.2072 0.6632 0.063 Uiso 1 1 calc R U . . .
H14 H 0.2224 0.1626 0.6191 0.063 Uiso 1 1 calc R U . . .
Cl1 Cl -0.2500 0.2500 0.64485(7) 0.0504(3) Uani 1 2 d S T P . .


_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
O1 C1 1.321(3) . ?
O1 Mn1 1.8713(19) . ?
C1 C2 1.396(4) . ?
C1 C6 1.406(4) . ?
C2 C3 1.367(5) . ?
C2 H1 0.9300 . ?
C3 C4 1.379(5) . ?
C3 H2 0.9300 . ?
C4 C5 1.364(5) . ?
C4 H3 0.9300 . ?
C5 C6 1.402(4) . ?
C5 H4 0.9300 . ?
C6 C7 1.438(4) . ?
C7 N1 1.284(4) . ?
C7 H5 0.9300 . ?
N1 C8 1.469(4) . ?
N1 Mn1 2.022(3) . ?
Mn1 O1 1.8712(19) 2 ?
Mn1 N1 2.022(3) 2 ?
Mn1 N2 2.097(3) . ?
Mn1 N2 2.097(3) 2 ?
C8 C9 1.516(5) . ?
C8 H7 0.9700 . ?
C8 H6 0.9700 . ?
C9 C10 1.508(5) . ?
C9 H8 0.9700 . ?
C9 H9 0.9700 . ?
C10 N2 1.478(4) . ?
C10 H11 0.9700 . ?
C10 H10 0.9700 . ?
N2 C11 1.468(4) . ?
N2 H12 0.86(4) . ?
C11 C11 1.512(8) 2 ?
C11 H13 0.9700 . ?
C11 H14 0.9700 . ?

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
C1 O1 Mn1 126.07(17) . . ?
O1 C1 C2 119.2(3) . . ?
O1 C1 C6 122.6(3) . . ?
C2 C1 C6 118.2(3) . . ?
C3 C2 C1 121.2(3) . . ?
C3 C2 H1 119.4 . . ?
C1 C2 H1 119.4 . . ?
C2 C3 C4 120.7(3) . . ?
C2 C3 H2 119.6 . . ?
C4 C3 H2 119.6 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H3 120.3 . . ?
C3 C4 H3 120.3 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H4 119.3 . . ?
C6 C5 H4 119.3 . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 C7 119.3(3) . . ?
C1 C6 C7 121.2(3) . . ?
N1 C7 C6 124.7(3) . . ?
N1 C7 H5 117.6 . . ?
C6 C7 H5 117.6 . . ?
C7 N1 C8 117.0(3) . . ?
C7 N1 Mn1 124.0(2) . . ?
C8 N1 Mn1 118.5(2) . . ?
O1 Mn1 O1 177.87(12) 2 . ?
O1 Mn1 N1 93.81(10) 2 . ?
O1 Mn1 N1 87.55(9) . . ?
O1 Mn1 N1 87.55(9) 2 2 ?
O1 Mn1 N1 93.81(10) . 2 ?
N1 Mn1 N1 100.59(14) . 2 ?
O1 Mn1 N2 85.81(9) 2 . ?
O1 Mn1 N2 92.60(10) . . ?
N1 Mn1 N2 87.97(11) . . ?
N1 Mn1 N2 169.51(10) 2 . ?
O1 Mn1 N2 92.60(10) 2 2 ?
O1 Mn1 N2 85.81(9) . 2 ?
N1 Mn1 N2 169.50(10) . 2 ?
N1 Mn1 N2 87.97(11) 2 2 ?
N2 Mn1 N2 84.22(15) . 2 ?
N1 C8 C9 109.7(2) . . ?
N1 C8 H7 109.7 . . ?
C9 C8 H7 109.7 . . ?
N1 C8 H6 109.7 . . ?
C9 C8 H6 109.7 . . ?
H7 C8 H6 108.2 . . ?
C10 C9 C8 115.3(3) . . ?
C10 C9 H8 108.5 . . ?
C8 C9 H8 108.5 . . ?
C10 C9 H9 108.5 . . ?
C8 C9 H9 108.5 . . ?
H8 C9 H9 107.5 . . ?
N2 C10 C9 112.3(3) . . ?
N2 C10 H11 109.1 . . ?
C9 C10 H11 109.1 . . ?
N2 C10 H10 109.1 . . ?
C9 C10 H10 109.1 . . ?
H11 C10 H10 107.9 . . ?
C11 N2 C10 112.3(3) . . ?
C11 N2 Mn1 105.9(2) . . ?
C10 N2 Mn1 116.36(19) . . ?
C11 N2 H12 106(2) . . ?
C10 N2 H12 108(2) . . ?
Mn1 N2 H12 107(2) . . ?
N2 C11 C11 109.0(2) . 2 ?
N2 C11 H13 109.9 . . ?
C11 C11 H13 109.9 2 . ?
N2 C11 H14 109.9 . . ?
C11 C11 H14 109.9 2 . ?
H13 C11 H14 108.3 . . ?

_refine_diff_density_max         0.375
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.064

