# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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
_audit_block_doi                 10.5517/ccdc.csd.cc1yv521
_database_code_depnum_ccdc_archive 'CCDC 1812603'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/c8ce00061a 2018
_audit_update_record             
;
2018-04-03 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H24 Cu F12 N3 O5'
_chemical_formula_weight         738.01

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'
Cu Cu 0.3201 1.2651 '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'
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      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                   9.8939(14)
_cell_length_b                   18.898(3)
_cell_length_c                   16.637(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.438(4)
_cell_angle_gamma                90
_cell_volume                     3091.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9058
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      28.27

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.380
_exptl_absorpt_coefficient_mu    0.818
_shelx_estimated_absorpt_T_min   0.676
_shelx_estimated_absorpt_T_max   0.746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.669
_exptl_absorpt_correction_T_max  0.733
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48832
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.990
_diffrn_reflns_theta_max         28.319
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7661
_reflns_number_gt                5894
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0646P)²+2.3222P] 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         7661
_refine_ls_number_parameters     473
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1391
_refine_ls_wR_factor_gt          0.1243
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.2288(2) 0.88270(10) 0.26980(12) 0.0635(5) Uani 1 1 d . . . . .
N1 N 0.1842(2) 0.83807(10) 0.31861(12) 0.0481(4) Uani 1 1 d . . . . .
N2 N 0.0617(2) 0.68198(11) 0.47659(14) 0.0578(5) Uani 1 1 d . . . . .
N3 N 0.08458(19) 0.51852(9) 0.64279(10) 0.0389(4) Uani 1 1 d . . . . .
C1 C 0.0905(3) 0.78310(13) 0.28055(15) 0.0546(6) Uani 1 1 d . . . . .
C2 C 0.0787(3) 0.72235(13) 0.34032(16) 0.0584(6) Uani 1 1 d . . . . .
H2A H 0.003098 0.692412 0.319634 0.070 Uiso 1 1 calc R U . . .
H2B H 0.160794 0.693957 0.342881 0.070 Uiso 1 1 calc R U . . .
C3 C 0.0580(3) 0.74535(13) 0.42506(16) 0.0550(6) Uani 1 1 d . . . . .
H3 H -0.028674 0.770383 0.425393 0.066 Uiso 1 1 calc R U . . .
C4 C 0.1758(3) 0.79235(14) 0.45688(16) 0.0589(6) Uani 1 1 d . . . . .
H4A H 0.258819 0.764716 0.460306 0.071 Uiso 1 1 calc R U . . .
H4B H 0.162701 0.807200 0.511289 0.071 Uiso 1 1 calc R U . . .
C5 C 0.1942(3) 0.85845(13) 0.40574(15) 0.0532(6) Uani 1 1 d . . . . .
C6 C 0.1522(4) 0.75447(17) 0.20670(18) 0.0768(9) Uani 1 1 d . . . . .
H6A H 0.156248 0.791666 0.167747 0.115 Uiso 1 1 calc R U . . .
H6B H 0.096794 0.716565 0.182944 0.115 Uiso 1 1 calc R U . . .
H6C H 0.242382 0.737208 0.223104 0.115 Uiso 1 1 calc R U . . .
C7 C -0.0483(3) 0.81676(17) 0.2548(2) 0.0741(9) Uani 1 1 d . . . . .
H7A H -0.092898 0.826725 0.301872 0.111 Uiso 1 1 calc R U . . .
H7B H -0.102965 0.784696 0.220180 0.111 Uiso 1 1 calc R U . . .
H7C H -0.036034 0.859977 0.226146 0.111 Uiso 1 1 calc R U . . .
C8 C 0.3355(4) 0.88909(18) 0.42844(19) 0.0764(9) Uani 1 1 d . . . . .
H8A H 0.402410 0.857046 0.411950 0.115 Uiso 1 1 calc R U . . .
H8B H 0.350509 0.895815 0.485942 0.115 Uiso 1 1 calc R U . . .
H8C H 0.342620 0.933753 0.401749 0.115 Uiso 1 1 calc R U . . .
C9 C 0.0860(4) 0.91439(16) 0.4170(2) 0.0778(9) Uani 1 1 d . . . . .
H9A H 0.090549 0.951396 0.377868 0.117 Uiso 1 1 calc R U . . .
H9B H 0.102039 0.933902 0.470493 0.117 Uiso 1 1 calc R U . . .
H9C H -0.002518 0.892948 0.409695 0.117 Uiso 1 1 calc R U . . .
C10 C -0.0471(3) 0.65476(12) 0.49201(13) 0.0459(5) Uani 1 1 d . . . . .
H10 H -0.129607 0.674458 0.470719 0.055 Uiso 1 1 calc R U . . .
C11 C -0.0457(2) 0.59097(11) 0.54426(12) 0.0413(4) Uani 1 1 d . . . . .
C12 C -0.1570(2) 0.54773(13) 0.54727(15) 0.0493(5) Uani 1 1 d . . . . .
H12 H -0.237866 0.556924 0.514830 0.059 Uiso 1 1 calc R U . . .
C13 C -0.1467(3) 0.49057(14) 0.59912(17) 0.0542(6) Uani 1 1 d . . . . .
H13 H -0.220963 0.460870 0.602106 0.065 Uiso 1 1 calc R U . . .
C14 C -0.0260(3) 0.47775(12) 0.64643(14) 0.0468(5) Uani 1 1 d . . . . .
H14 H -0.020720 0.439684 0.682069 0.056 Uiso 1 1 calc R U . . .
C15 C 0.0732(2) 0.57407(11) 0.59229(12) 0.0403(4) Uani 1 1 d . . . . .
H15 H 0.149002 0.602646 0.589413 0.048 Uiso 1 1 calc R U . . .
C16 C 0.4154(4) 0.28209(19) 0.6659(2) 0.0791(9) Uani 1 1 d . . . . .
F1 F 0.3825(11) 0.2713(5) 0.5900(4) 0.105(3) Uani 0.5 1 d . . P A -1
F2 F 0.4220(19) 0.2255(7) 0.7075(10) 0.157(7) Uani 0.5 1 d . . P A -1
F3 F 0.5416(10) 0.3046(9) 0.6648(9) 0.158(6) Uani 0.5 1 d . . P A -1
C17 C 0.3351(3) 0.34242(13) 0.70030(15) 0.0510(5) Uani 1 1 d . . . . .
C18 C 0.3040(3) 0.33558(13) 0.78040(15) 0.0544(6) Uani 1 1 d . . . . .
H18 H 0.334957 0.295766 0.809767 0.065 Uiso 1 1 calc R U . . .
C19 C 0.2305(3) 0.38475(12) 0.81690(14) 0.0497(5) Uani 1 1 d . . . . .
C20 C 0.1998(5) 0.37022(17) 0.90297(18) 0.0776(10) Uani 1 1 d . . . . .
F4 F 0.2156(5) 0.30651(13) 0.92616(15) 0.1689(16) Uani 1 1 d . . . . .
F5 F 0.0674(4) 0.3817(2) 0.90869(18) 0.1589(14) Uani 1 1 d . . . . .
F6 F 0.2540(5) 0.41379(18) 0.95320(13) 0.1685(16) Uani 1 1 d . . . . .
C21 C 0.6665(5) 0.4988(3) 0.8291(3) 0.1029(17) Uani 1 1 d . . . . .
F7 F 0.7003(17) 0.4332(6) 0.8156(12) 0.178(5) Uani 0.5 1 d . . P B 1
F8 F 0.6226(12) 0.5011(7) 0.9023(5) 0.127(3) Uani 0.5 1 d . . P B 1
F10 F 0.7664(16) 0.5401(12) 0.8307(13) 0.224(12) Uani 0.5 1 d . . P B 1
C22 C 0.5463(3) 0.51932(15) 0.76669(16) 0.0564(6) Uani 1 1 d . . . . .
C23 C 0.5710(3) 0.56713(16) 0.70714(18) 0.0632(7) Uani 1 1 d . . . . .
H23 H 0.655037 0.589451 0.709110 0.076 Uiso 1 1 calc R U . . .
C24 C 0.4715(3) 0.58161(13) 0.64525(16) 0.0540(6) Uani 1 1 d . . . . .
C25 C 0.5006(3) 0.6354(2) 0.5802(2) 0.0829(10) Uani 1 1 d . . . . .
Cu1 Cu 0.26326(3) 0.49986(2) 0.70854(2) 0.04260(10) Uani 1 1 d . . . . .
O2 O 0.3033(2) 0.39071(9) 0.65254(10) 0.0562(4) Uani 1 1 d . . . . .
O3 O 0.18221(18) 0.44317(8) 0.78968(9) 0.0495(4) Uani 1 1 d . . . . .
O4 O 0.4379(2) 0.48874(10) 0.77625(11) 0.0544(4) Uani 1 1 d . . . . .
O5 O 0.35413(18) 0.55578(10) 0.63225(10) 0.0541(4) Uani 1 1 d . . . . .
F11 F 0.6231(2) 0.66329(12) 0.59169(16) 0.1071(8) Uani 1 1 d . . . . .
F12 F 0.4956(3) 0.6034(2) 0.50977(15) 0.1386(13) Uani 1 1 d . . . . .
F13 F 0.4143(3) 0.68650(16) 0.5760(2) 0.1712(17) Uani 1 1 d . . . . .
F14 F 0.7764(9) 0.4965(12) 0.8037(7) 0.165(7) Uani 0.5 1 d . . P B -1
F16 F 0.6481(15) 0.4467(15) 0.8696(13) 0.237(12) Uani 0.5 1 d . . P B -1
F15 F 0.691(2) 0.5512(15) 0.8796(10) 0.245(9) Uani 0.5 1 d . . P B -1
F17 F 0.3281(12) 0.2430(6) 0.6160(8) 0.168(5) Uani 0.5 1 d . . P A 1
F18 F 0.4673(16) 0.2378(8) 0.7196(11) 0.134(5) Uani 0.5 1 d . . P A 1
F19 F 0.5164(15) 0.3021(6) 0.6339(10) 0.161(8) Uani 0.5 1 d . . P A 1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.283(3) . ?
N1 C1 1.485(3) . ?
N1 C5 1.493(3) . ?
N2 C10 1.246(3) . ?
N2 C3 1.471(3) . ?
N3 C15 1.341(3) . ?
N3 C14 1.345(3) . ?
N3 Cu1 2.0032(19) . ?
C1 C7 1.531(4) . ?
C1 C6 1.531(4) . ?
C1 C2 1.532(3) . ?
C2 C3 1.511(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.513(4) . ?
C3 H3 0.9800 . ?
C4 C5 1.534(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C8 1.521(4) . ?
C5 C9 1.531(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.485(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(3) . ?
C11 C15 1.383(3) . ?
C12 C13 1.379(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 F19 1.243(11) . ?
C16 F2 1.272(12) . ?
C16 F1 1.284(8) . ?
C16 F18 1.288(12) . ?
C16 F3 1.321(12) . ?
C16 F17 1.349(11) . ?
C16 C17 1.537(4) . ?
F1 F17 0.902(13) . ?
F1 F19 1.553(18) . ?
F2 F18 0.52(3) . ?
F2 F17 1.72(2) . ?
F3 F19 0.55(2) . ?
F3 F18 1.77(2) . ?
C17 O2 1.227(3) . ?
C17 C18 1.407(3) . ?
C18 C19 1.364(4) . ?
C18 H18 0.9300 . ?
C19 O3 1.266(3) . ?
C19 C20 1.522(4) . ?
C20 F6 1.250(4) . ?
C20 F4 1.269(4) . ?
C20 F5 1.342(5) . ?
C21 F14 1.210(10) . ?
C21 F16 1.220(14) . ?
C21 F10 1.257(10) . ?
C21 F15 1.304(17) . ?
C21 F7 1.309(10) . ?
C21 F8 1.340(12) . ?
C21 C22 1.538(5) . ?
F7 F16 1.12(2) . ?
F7 F14 1.438(16) . ?
F8 F16 1.20(3) . ?
F8 F15 1.24(3) . ?
F10 F14 0.95(2) . ?
F10 F15 1.19(2) . ?
C22 O4 1.244(3) . ?
C22 C23 1.382(4) . ?
C23 C24 1.370(4) . ?
C23 H23 0.9300 . ?
C24 O5 1.256(3) . ?
C24 C25 1.535(4) . ?
C25 F13 1.287(4) . ?
C25 F12 1.315(5) . ?
C25 F11 1.316(4) . ?
Cu1 O5 1.9472(16) . ?
Cu1 O3 1.9637(15) . ?
Cu1 O4 1.9655(18) . ?
Cu1 O2 2.3158(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 C1 115.62(19) . . ?
O1 N1 C5 117.07(19) . . ?
C1 N1 C5 124.38(19) . . ?
C10 N2 C3 119.4(2) . . ?
C15 N3 C14 117.7(2) . . ?
C15 N3 Cu1 119.14(15) . . ?
C14 N3 Cu1 123.17(15) . . ?
N1 C1 C7 109.0(2) . . ?
N1 C1 C6 107.7(2) . . ?
C7 C1 C6 110.4(2) . . ?
N1 C1 C2 109.68(19) . . ?
C7 C1 C2 111.2(2) . . ?
C6 C1 C2 108.8(2) . . ?
C3 C2 C1 114.7(2) . . ?
C3 C2 H2A 108.6 . . ?
C1 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
C1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
N2 C3 C2 108.2(2) . . ?
N2 C3 C4 107.8(2) . . ?
C2 C3 C4 108.4(2) . . ?
N2 C3 H3 110.8 . . ?
C2 C3 H3 110.8 . . ?
C4 C3 H3 110.8 . . ?
C3 C4 C5 114.8(2) . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
C5 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
N1 C5 C8 107.3(2) . . ?
N1 C5 C9 109.0(2) . . ?
C8 C5 C9 110.0(3) . . ?
N1 C5 C4 109.2(2) . . ?
C8 C5 C4 109.6(2) . . ?
C9 C5 C4 111.5(2) . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C11 120.3(2) . . ?
N2 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C15 118.3(2) . . ?
C12 C11 C10 123.2(2) . . ?
C15 C11 C10 118.5(2) . . ?
C11 C12 C13 119.0(2) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C14 C13 C12 119.6(2) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
N3 C14 C13 122.1(2) . . ?
N3 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
N3 C15 C11 123.3(2) . . ?
N3 C15 H15 118.4 . . ?
C11 C15 H15 118.4 . . ?
F19 C16 F2 119.6(9) . . ?
F19 C16 F1 75.8(8) . . ?
F2 C16 F1 113.1(9) . . ?
F19 C16 F18 102.6(10) . . ?
F2 C16 F18 23.6(15) . . ?
F1 C16 F18 128.0(9) . . ?
F19 C16 F3 24.4(11) . . ?
F2 C16 F3 106.7(10) . . ?
F1 C16 F3 100.0(7) . . ?
F18 C16 F3 85.1(10) . . ?
F19 C16 F17 113.2(9) . . ?
F2 C16 F17 82.2(10) . . ?
F1 C16 F17 40.0(6) . . ?
F18 C16 F17 104.4(10) . . ?
F3 C16 F17 135.2(8) . . ?
F19 C16 C17 114.1(6) . . ?
F2 C16 C17 114.8(8) . . ?
F1 C16 C17 113.5(4) . . ?
F18 C16 C17 114.0(8) . . ?
F3 C16 C17 107.2(7) . . ?
F17 C16 C17 108.2(5) . . ?
F17 F1 C16 73.8(10) . . ?
F17 F1 F19 121.3(13) . . ?
C16 F1 F19 50.9(5) . . ?
F18 F2 C16 80(3) . . ?
F18 F2 F17 127(3) . . ?
C16 F2 F17 50.8(7) . . ?
F19 F3 C16 70(2) . . ?
F19 F3 F18 105(3) . . ?
C16 F3 F18 46.7(6) . . ?
O2 C17 C18 127.9(2) . . ?
O2 C17 C16 114.6(2) . . ?
C18 C17 C16 117.5(2) . . ?
C19 C18 C17 122.9(2) . . ?
C19 C18 H18 118.6 . . ?
C17 C18 H18 118.6 . . ?
O3 C19 C18 129.3(2) . . ?
O3 C19 C20 112.8(2) . . ?
C18 C19 C20 118.0(2) . . ?
F6 C20 F4 113.1(3) . . ?
F6 C20 F5 101.3(4) . . ?
F4 C20 F5 102.7(4) . . ?
F6 C20 C19 113.2(3) . . ?
F4 C20 C19 115.2(3) . . ?
F5 C20 C19 109.7(3) . . ?
F14 C21 F16 111.1(11) . . ?
F14 C21 F10 45.2(11) . . ?
F16 C21 F10 131.0(9) . . ?
F14 C21 F15 98.4(10) . . ?
F16 C21 F15 106.5(12) . . ?
F10 C21 F15 55.1(9) . . ?
F14 C21 F7 69.5(9) . . ?
F16 C21 F7 52.2(11) . . ?
F10 C21 F7 112.1(12) . . ?
F15 C21 F7 142.9(9) . . ?
F14 C21 F8 135.6(8) . . ?
F16 C21 F8 55.8(14) . . ?
F10 C21 F8 107.2(12) . . ?
F15 C21 F8 56.2(11) . . ?
F7 C21 F8 107.5(10) . . ?
F14 C21 C22 115.5(6) . . ?
F16 C21 C22 115.1(6) . . ?
F10 C21 C22 113.9(7) . . ?
F15 C21 C22 108.4(8) . . ?
F7 C21 C22 108.4(6) . . ?
F8 C21 C22 107.5(6) . . ?
F16 F7 C21 59.8(11) . . ?
F16 F7 F14 102.6(15) . . ?
C21 F7 F14 52.0(6) . . ?
F16 F8 F15 111.5(16) . . ?
F16 F8 C21 57.0(8) . . ?
F15 F8 C21 60.5(8) . . ?
F14 F10 F15 125.9(18) . . ?
F14 F10 C21 64.8(9) . . ?
F15 F10 C21 64.5(10) . . ?
O4 C22 C23 128.2(3) . . ?
O4 C22 C21 114.2(3) . . ?
C23 C22 C21 117.6(3) . . ?
C24 C23 C22 120.0(3) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
O5 C24 C23 128.6(2) . . ?
O5 C24 C25 112.3(2) . . ?
C23 C24 C25 119.1(3) . . ?
F13 C25 F12 109.8(4) . . ?
F13 C25 F11 107.6(3) . . ?
F12 C25 F11 104.8(3) . . ?
F13 C25 C24 111.1(3) . . ?
F12 C25 C24 109.4(3) . . ?
F11 C25 C24 113.9(3) . . ?
O5 Cu1 O3 176.52(7) . . ?
O5 Cu1 O4 89.49(7) . . ?
O3 Cu1 O4 87.03(7) . . ?
O5 Cu1 N3 89.55(7) . . ?
O3 Cu1 N3 93.90(7) . . ?
O4 Cu1 N3 175.73(7) . . ?
O5 Cu1 O2 96.25(7) . . ?
O3 Cu1 O2 83.80(7) . . ?
O4 Cu1 O2 87.49(7) . . ?
N3 Cu1 O2 96.75(7) . . ?
C17 O2 Cu1 116.41(16) . . ?
C19 O3 Cu1 123.69(16) . . ?
C22 O4 Cu1 126.31(17) . . ?
C24 O5 Cu1 125.75(16) . . ?
F10 F14 C21 70.0(11) . . ?
F10 F14 F7 125.0(16) . . ?
C21 F14 F7 58.5(7) . . ?
F7 F16 F8 134.3(19) . . ?
F7 F16 C21 68.0(8) . . ?
F8 F16 C21 67.1(14) . . ?
F10 F15 F8 119(2) . . ?
F10 F15 C21 60.4(10) . . ?
F8 F15 C21 63.4(13) . . ?
F1 F17 C16 66.2(10) . . ?
F1 F17 F2 104.2(14) . . ?
C16 F17 F2 47.0(6) . . ?
F2 F18 C16 76(2) . . ?
F2 F18 F3 120(3) . . ?
C16 F18 F3 48.2(7) . . ?
F3 F19 C16 86(2) . . ?
F3 F19 F1 138(2) . . ?
C16 F19 F1 53.3(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 C7 -74.4(3) . . . . ?
C5 N1 C1 C7 85.6(3) . . . . ?
O1 N1 C1 C6 45.4(3) . . . . ?
C5 N1 C1 C6 -154.6(2) . . . . ?
O1 N1 C1 C2 163.6(2) . . . . ?
C5 N1 C1 C2 -36.4(3) . . . . ?
N1 C1 C2 C3 45.8(3) . . . . ?
C7 C1 C2 C3 -74.9(3) . . . . ?
C6 C1 C2 C3 163.3(3) . . . . ?
C10 N2 C3 C2 -99.1(3) . . . . ?
C10 N2 C3 C4 143.8(3) . . . . ?
C1 C2 C3 N2 -174.7(2) . . . . ?
C1 C2 C3 C4 -58.0(3) . . . . ?
N2 C3 C4 C5 175.2(2) . . . . ?
C2 C3 C4 C5 58.3(3) . . . . ?
O1 N1 C5 C8 -45.0(3) . . . . ?
C1 N1 C5 C8 155.3(2) . . . . ?
O1 N1 C5 C9 74.1(3) . . . . ?
C1 N1 C5 C9 -85.6(3) . . . . ?
O1 N1 C5 C4 -163.8(2) . . . . ?
C1 N1 C5 C4 36.5(3) . . . . ?
C3 C4 C5 N1 -46.1(3) . . . . ?
C3 C4 C5 C8 -163.5(3) . . . . ?
C3 C4 C5 C9 74.4(3) . . . . ?
C3 N2 C10 C11 -179.7(2) . . . . ?
N2 C10 C11 C12 -162.7(2) . . . . ?
N2 C10 C11 C15 17.3(3) . . . . ?
C15 C11 C12 C13 1.5(3) . . . . ?
C10 C11 C12 C13 -178.5(2) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C15 N3 C14 C13 1.6(3) . . . . ?
Cu1 N3 C14 C13 -178.30(19) . . . . ?
C12 C13 C14 N3 -1.4(4) . . . . ?
C14 N3 C15 C11 -0.1(3) . . . . ?
Cu1 N3 C15 C11 179.72(16) . . . . ?
C12 C11 C15 N3 -1.4(3) . . . . ?
C10 C11 C15 N3 178.63(19) . . . . ?
F19 C16 F1 F17 158.9(12) . . . . ?
F2 C16 F1 F17 42.4(14) . . . . ?
F18 C16 F1 F17 63.9(16) . . . . ?
F3 C16 F1 F17 155.5(12) . . . . ?
C17 C16 F1 F17 -90.7(11) . . . . ?
F2 C16 F1 F19 -116.5(10) . . . . ?
F18 C16 F1 F19 -95.1(12) . . . . ?
F3 C16 F1 F19 -3.4(11) . . . . ?
F17 C16 F1 F19 -158.9(12) . . . . ?
C17 C16 F1 F19 110.4(6) . . . . ?
F19 C16 F2 F18 48(4) . . . . ?
F1 C16 F2 F18 134(3) . . . . ?
F3 C16 F2 F18 25(4) . . . . ?
F17 C16 F2 F18 160(4) . . . . ?
C17 C16 F2 F18 -94(3) . . . . ?
F19 C16 F2 F17 -112.3(11) . . . . ?
F1 C16 F2 F17 -25.9(8) . . . . ?
F18 C16 F2 F17 -160(4) . . . . ?
F3 C16 F2 F17 -134.9(9) . . . . ?
C17 C16 F2 F17 106.6(7) . . . . ?
F2 C16 F3 F19 126(3) . . . . ?
F1 C16 F3 F19 8(3) . . . . ?
F18 C16 F3 F19 136(3) . . . . ?
F17 C16 F3 F19 30(3) . . . . ?
C17 C16 F3 F19 -111(3) . . . . ?
F19 C16 F3 F18 -136(3) . . . . ?
F2 C16 F3 F18 -9.8(15) . . . . ?
F1 C16 F3 F18 -127.8(9) . . . . ?
F17 C16 F3 F18 -105.6(13) . . . . ?
C17 C16 F3 F18 113.6(9) . . . . ?
F19 C16 C17 O2 51.8(10) . . . . ?
F2 C16 C17 O2 -164.9(11) . . . . ?
F1 C16 C17 O2 -32.6(8) . . . . ?
F18 C16 C17 O2 169.2(10) . . . . ?
F3 C16 C17 O2 76.9(8) . . . . ?
F17 C16 C17 O2 -75.1(8) . . . . ?
F19 C16 C17 C18 -129.7(10) . . . . ?
F2 C16 C17 C18 13.7(11) . . . . ?
F1 C16 C17 C18 146.0(7) . . . . ?
F18 C16 C17 C18 -12.3(10) . . . . ?
F3 C16 C17 C18 -104.6(7) . . . . ?
F17 C16 C17 C18 103.4(8) . . . . ?
O2 C17 C18 C19 -0.1(5) . . . . ?
C16 C17 C18 C19 -178.4(3) . . . . ?
C17 C18 C19 O3 -2.3(5) . . . . ?
C17 C18 C19 C20 178.1(3) . . . . ?
O3 C19 C20 F6 -64.0(5) . . . . ?
C18 C19 C20 F6 115.6(4) . . . . ?
O3 C19 C20 F4 163.6(4) . . . . ?
C18 C19 C20 F4 -16.8(5) . . . . ?
O3 C19 C20 F5 48.3(4) . . . . ?
C18 C19 C20 F5 -132.0(3) . . . . ?
F14 C21 F7 F16 140.9(12) . . . . ?
F10 C21 F7 F16 125.5(12) . . . . ?
F15 C21 F7 F16 65(2) . . . . ?
F8 C21 F7 F16 8.0(12) . . . . ?
C22 C21 F7 F16 -108.0(10) . . . . ?
F16 C21 F7 F14 -140.9(12) . . . . ?
F10 C21 F7 F14 -15.4(12) . . . . ?
F15 C21 F7 F14 -76.4(19) . . . . ?
F8 C21 F7 F14 -132.9(9) . . . . ?
C22 C21 F7 F14 111.1(7) . . . . ?
F14 C21 F8 F16 -85.9(17) . . . . ?
F10 C21 F8 F16 -128.3(12) . . . . ?
F15 C21 F8 F16 -150.3(13) . . . . ?
F7 C21 F8 F16 -7.6(11) . . . . ?
C22 C21 F8 F16 108.9(8) . . . . ?
F14 C21 F8 F15 64.4(18) . . . . ?
F16 C21 F8 F15 150.3(13) . . . . ?
F10 C21 F8 F15 22.0(14) . . . . ?
F7 C21 F8 F15 142.7(10) . . . . ?
C22 C21 F8 F15 -100.7(10) . . . . ?
F16 C21 F10 F14 79(2) . . . . ?
F15 C21 F10 F14 160.6(18) . . . . ?
F7 C21 F10 F14 20.6(15) . . . . ?
F8 C21 F10 F14 138.3(13) . . . . ?
C22 C21 F10 F14 -103.0(12) . . . . ?
F14 C21 F10 F15 -160.6(18) . . . . ?
F16 C21 F10 F15 -82(2) . . . . ?
F7 C21 F10 F15 -140.0(13) . . . . ?
F8 C21 F10 F15 -22.3(15) . . . . ?
C22 C21 F10 F15 96.4(11) . . . . ?
F14 C21 C22 O4 144.7(13) . . . . ?
F16 C21 C22 O4 13(2) . . . . ?
F10 C21 C22 O4 -165.2(17) . . . . ?
F15 C21 C22 O4 -106.0(15) . . . . ?
F7 C21 C22 O4 69.2(13) . . . . ?
F8 C21 C22 O4 -46.7(8) . . . . ?
F14 C21 C22 C23 -34.0(14) . . . . ?
F16 C21 C22 C23 -166(2) . . . . ?
F10 C21 C22 C23 16.0(18) . . . . ?
F15 C21 C22 C23 75.3(16) . . . . ?
F7 C21 C22 C23 -109.5(13) . . . . ?
F8 C21 C22 C23 134.6(7) . . . . ?
O4 C22 C23 C24 -5.4(5) . . . . ?
C21 C22 C23 C24 173.2(4) . . . . ?
C22 C23 C24 O5 -1.4(5) . . . . ?
C22 C23 C24 C25 179.4(3) . . . . ?
O5 C24 C25 F13 58.6(5) . . . . ?
C23 C24 C25 F13 -122.1(4) . . . . ?
O5 C24 C25 F12 -62.7(3) . . . . ?
C23 C24 C25 F12 116.6(3) . . . . ?
O5 C24 C25 F11 -179.7(3) . . . . ?
C23 C24 C25 F11 -0.4(5) . . . . ?
C18 C17 O2 Cu1 25.5(4) . . . . ?
C16 C17 O2 Cu1 -156.1(2) . . . . ?
C18 C19 O3 Cu1 -28.7(4) . . . . ?
C20 C19 O3 Cu1 151.0(2) . . . . ?
C23 C22 O4 Cu1 -0.6(5) . . . . ?
C21 C22 O4 Cu1 -179.2(3) . . . . ?
C23 C24 O5 Cu1 12.9(4) . . . . ?
C25 C24 O5 Cu1 -167.8(2) . . . . ?
F15 F10 F14 C21 21.7(17) . . . . ?
F15 F10 F14 F7 1(3) . . . . ?
C21 F10 F14 F7 -21.2(13) . . . . ?
F16 C21 F14 F10 -127.4(16) . . . . ?
F15 C21 F14 F10 -16.0(15) . . . . ?
F7 C21 F14 F10 -159.7(15) . . . . ?
F8 C21 F14 F10 -65(2) . . . . ?
C22 C21 F14 F10 99.1(13) . . . . ?
F16 C21 F14 F7 32.3(12) . . . . ?
F10 C21 F14 F7 159.7(15) . . . . ?
F15 C21 F14 F7 143.7(10) . . . . ?
F8 C21 F14 F7 94.4(16) . . . . ?
C22 C21 F14 F7 -101.3(8) . . . . ?
F16 F7 F14 F10 -10(2) . . . . ?
C21 F7 F14 F10 23.5(15) . . . . ?
F16 F7 F14 C21 -33.9(8) . . . . ?
C21 F7 F16 F8 -11.9(15) . . . . ?
F14 F7 F16 F8 19(2) . . . . ?
F14 F7 F16 C21 30.6(7) . . . . ?
F15 F8 F16 F7 -16(2) . . . . ?
C21 F8 F16 F7 12.0(15) . . . . ?
F15 F8 F16 C21 -27.6(9) . . . . ?
F14 C21 F16 F7 -39.2(13) . . . . ?
F10 C21 F16 F7 -88(2) . . . . ?
F15 C21 F16 F7 -145.4(11) . . . . ?
F8 C21 F16 F7 -170.8(13) . . . . ?
C22 C21 F16 F7 94.5(10) . . . . ?
F14 C21 F16 F8 131.6(10) . . . . ?
F10 C21 F16 F8 83.3(19) . . . . ?
F15 C21 F16 F8 25.4(11) . . . . ?
F7 C21 F16 F8 170.8(13) . . . . ?
C22 C21 F16 F8 -94.7(11) . . . . ?
F14 F10 F15 F8 5(3) . . . . ?
C21 F10 F15 F8 26.4(10) . . . . ?
F14 F10 F15 C21 -21.8(17) . . . . ?
F16 F8 F15 F10 0.9(17) . . . . ?
C21 F8 F15 F10 -25.6(10) . . . . ?
F16 F8 F15 C21 26.5(9) . . . . ?
F14 C21 F15 F10 13.8(14) . . . . ?
F16 C21 F15 F10 128.8(12) . . . . ?
F7 C21 F15 F10 81(2) . . . . ?
F8 C21 F15 F10 154.1(15) . . . . ?
C22 C21 F15 F10 -106.8(10) . . . . ?
F14 C21 F15 F8 -140.3(9) . . . . ?
F16 C21 F15 F8 -25.3(12) . . . . ?
F10 C21 F15 F8 -154.1(15) . . . . ?
F7 C21 F15 F8 -73.4(19) . . . . ?
C22 C21 F15 F8 99.1(9) . . . . ?
F19 F1 F17 C16 19.1(10) . . . . ?
C16 F1 F17 F2 -28.2(8) . . . . ?
F19 F1 F17 F2 -9.1(16) . . . . ?
F19 C16 F17 F1 -22.3(13) . . . . ?
F2 C16 F17 F1 -141.3(13) . . . . ?
F18 C16 F17 F1 -133.1(12) . . . . ?
F3 C16 F17 F1 -35.4(17) . . . . ?
C17 C16 F17 F1 105.2(10) . . . . ?
F19 C16 F17 F2 119.0(9) . . . . ?
F1 C16 F17 F2 141.3(13) . . . . ?
F18 C16 F17 F2 8.2(15) . . . . ?
F3 C16 F17 F2 105.9(13) . . . . ?
C17 C16 F17 F2 -113.6(8) . . . . ?
F18 F2 F17 F1 11(5) . . . . ?
C16 F2 F17 F1 36.2(11) . . . . ?
F18 F2 F17 C16 -25(4) . . . . ?
F17 F2 F18 C16 20(3) . . . . ?
C16 F2 F18 F3 -21(2) . . . . ?
F17 F2 F18 F3 -1(5) . . . . ?
F19 C16 F18 F2 -139(3) . . . . ?
F1 C16 F18 F2 -57(4) . . . . ?
F3 C16 F18 F2 -156(4) . . . . ?
F17 C16 F18 F2 -21(4) . . . . ?
C17 C16 F18 F2 97(3) . . . . ?
F19 C16 F18 F3 17.2(13) . . . . ?
F2 C16 F18 F3 156(4) . . . . ?
F1 C16 F18 F3 98.9(11) . . . . ?
F17 C16 F18 F3 135.5(9) . . . . ?
C17 C16 F18 F3 -106.6(9) . . . . ?
F19 F3 F18 F2 -15(5) . . . . ?
C16 F3 F18 F2 27(3) . . . . ?
F19 F3 F18 C16 -42(2) . . . . ?
F18 F3 F19 C16 31.6(14) . . . . ?
C16 F3 F19 F1 -10(3) . . . . ?
F18 F3 F19 F1 22(4) . . . . ?
F2 C16 F19 F3 -63(3) . . . . ?
F1 C16 F19 F3 -172(3) . . . . ?
F18 C16 F19 F3 -45(3) . . . . ?
F17 C16 F19 F3 -157(3) . . . . ?
C17 C16 F19 F3 78(3) . . . . ?
F2 C16 F19 F1 108.8(12) . . . . ?
F18 C16 F19 F1 126.5(9) . . . . ?
F3 C16 F19 F1 172(3) . . . . ?
F17 C16 F19 F1 14.6(9) . . . . ?
C17 C16 F19 F1 -109.8(6) . . . . ?
F17 F1 F19 F3 -11(5) . . . . ?
C16 F1 F19 F3 12(4) . . . . ?
F17 F1 F19 C16 -23.8(13) . . . . ?

_refine_diff_density_max         0.863
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.056

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

data_4
_audit_block_doi                 10.5517/ccdc.csd.cc1yv510
_database_code_depnum_ccdc_archive 'CCDC 1812602'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/c8ce00061a 2018
_audit_update_record             
;
2018-04-03 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H24 F12 Mn N3 O5'
_chemical_formula_weight         729.41

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'
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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   18.4213(8)
_cell_length_b                   18.1732(8)
_cell_length_c                   19.0497(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6377.3(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9976
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      26.12

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_F_000             2944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.522
_shelx_estimated_absorpt_T_min   0.903
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.769
_exptl_absorpt_correction_T_max  0.820
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            133929
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.077
_diffrn_reflns_theta_max         28.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7955
_reflns_number_gt                5414
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1241P)²+6.7190P] 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         7955
_refine_ls_number_parameters     428
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0740
_refine_ls_wR_factor_ref         0.2461
_refine_ls_wR_factor_gt          0.2124
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.122
_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 0.21139(3) 0.37877(3) 0.22946(3) 0.05061(19) Uani 1 1 d . . . . .
F1 F 0.0017(3) 0.2779(2) 0.0503(2) 0.1536(17) Uani 1 1 d . . . . .
F3 F 0.0899(3) 0.2097(3) 0.0652(4) 0.195(3) Uani 1 1 d . . . . .
F4 F 0.0797(2) 0.5225(3) 0.0155(2) 0.1543(18) Uani 1 1 d . . . . .
F5 F 0.1849(7) 0.4986(7) -0.0042(7) 0.158(6) Uani 0.5 1 d . U P A -1
O4 O 0.13939(13) 0.43055(17) 0.30543(16) 0.0721(7) Uani 1 1 d . . . . .
F11 F 0.2204(3) 0.2071(3) 0.4390(3) 0.194(3) Uani 1 1 d . . . . .
F12 F 0.3192(3) 0.2383(3) 0.4020(3) 0.191(3) Uani 1 1 d . . . . .
F7 F 0.0812(3) 0.5390(3) 0.3736(3) 0.177(2) Uani 1 1 d . . . . .
F9 F 0.0410(3) 0.4580(4) 0.4326(4) 0.216(3) Uani 1 1 d . . . . .
F8 F 0.1376(3) 0.5096(4) 0.4630(3) 0.232(3) Uani 1 1 d . U . . .
O3 O 0.18169(15) 0.45434(14) 0.14880(16) 0.0712(7) Uani 1 1 d . . . . .
O2 O 0.13014(14) 0.31108(15) 0.17626(14) 0.0662(7) Uani 1 1 d . . . . .
O5 O 0.22861(14) 0.30380(14) 0.31416(13) 0.0626(6) Uani 1 1 d . . . . .
F10 F 0.2738(4) 0.2906(3) 0.4874(3) 0.204(3) Uani 1 1 d . U . . .
N2 N 0.49602(18) 0.66089(18) 0.32693(19) 0.0704(9) Uani 1 1 d . . . . .
O1 O 0.29337(15) 0.44983(17) 0.2681(2) 0.0855(10) Uani 1 1 d . . . . .
C8 C 0.4050(3) 0.4097(3) 0.3474(3) 0.1032(18) Uani 1 1 d . . . . .
H8A H 0.372313 0.425646 0.383595 0.155 Uiso 1 1 calc R U . . .
H8B H 0.450948 0.397086 0.367853 0.155 Uiso 1 1 calc R U . . .
H8C H 0.385046 0.367379 0.324173 0.155 Uiso 1 1 calc R U . . .
N3 N 0.30023(15) 0.32284(15) 0.16621(15) 0.0535(6) Uani 1 1 d . . . . .
C19 C 0.14116(19) 0.4463(2) 0.0970(2) 0.0647(9) Uani 1 1 d . . . . .
C18 C 0.1006(2) 0.3856(3) 0.0793(2) 0.0733(11) Uani 1 1 d . . . . .
H18 H 0.073356 0.386781 0.038218 0.088 Uiso 1 1 calc R U . . .
C17 C 0.0987(2) 0.3227(2) 0.12019(19) 0.0616(9) Uani 1 1 d . . . . .
C16 C 0.0516(3) 0.2587(3) 0.0945(3) 0.0867(13) Uani 1 1 d . . . . .
C20 C 0.1415(3) 0.5118(4) 0.0465(3) 0.1025(14) Uani 1 1 d . U . . .
C22 C 0.1451(2) 0.4262(3) 0.3697(3) 0.0767(12) Uani 1 1 d . . . . .
C23 C 0.1829(3) 0.3739(3) 0.4091(2) 0.0824(12) Uani 1 1 d . . . . .
H23 H 0.182768 0.377514 0.457787 0.099 Uiso 1 1 calc R U . . .
C24 C 0.2203(2) 0.3176(2) 0.3779(2) 0.0682(10) Uani 1 1 d . . . . .
C25 C 0.2579(4) 0.2641(3) 0.4273(3) 0.0998(16) Uani 1 1 d . . . . .
C21 C 0.1049(4) 0.4848(5) 0.4124(4) 0.131(3) Uani 1 1 d . . . . .
N1 N 0.34223(15) 0.49893(15) 0.27459(16) 0.0572(7) Uani 1 1 d . . . . .
C1 C 0.3266(3) 0.5732(2) 0.2477(4) 0.0962(17) Uani 1 1 d . . . . .
C2 C 0.3778(3) 0.6286(2) 0.2831(4) 0.0945(17) Uani 1 1 d . . . . .
H2A H 0.375451 0.674554 0.257347 0.113 Uiso 1 1 calc R U . . .
H2B H 0.360037 0.637998 0.330174 0.113 Uiso 1 1 calc R U . . .
C3 C 0.4554(2) 0.6054(2) 0.2879(2) 0.0649(9) Uani 1 1 d . . . . .
H3 H 0.476099 0.598861 0.240854 0.078 Uiso 1 1 calc R U . . .
C10 C 0.5531(2) 0.68642(19) 0.2997(2) 0.0603(8) Uani 1 1 d . . . . .
H10 H 0.568029 0.669436 0.255958 0.072 Uiso 1 1 calc R U . . .
C11 C 0.40346(18) 0.24269(18) 0.16389(18) 0.0549(8) Uani 1 1 d . . . . .
C4 C 0.4585(2) 0.5346(2) 0.3282(2) 0.0706(10) Uani 1 1 d . . . . .
H4A H 0.439763 0.543118 0.375068 0.085 Uiso 1 1 calc R U . . .
H4B H 0.508810 0.519633 0.332687 0.085 Uiso 1 1 calc R U . . .
C5 C 0.41543(19) 0.47130(19) 0.2945(2) 0.0603(8) Uani 1 1 d . . . . .
C9 C 0.4535(2) 0.4404(3) 0.2318(3) 0.1016(18) Uani 1 1 d . . . . .
H9A H 0.423723 0.403133 0.210613 0.152 Uiso 1 1 calc R U . . .
H9B H 0.498895 0.419291 0.245976 0.152 Uiso 1 1 calc R U . . .
H9C H 0.462158 0.479026 0.198407 0.152 Uiso 1 1 calc R U . . .
C7 C 0.3362(5) 0.5729(4) 0.1687(4) 0.165(4) Uani 1 1 d . . . . .
H7A H 0.386987 0.571765 0.157544 0.247 Uiso 1 1 calc R U . . .
H7B H 0.314723 0.616480 0.149219 0.247 Uiso 1 1 calc R U . . .
H7C H 0.312883 0.530238 0.149318 0.247 Uiso 1 1 calc R U . . .
C6 C 0.2488(3) 0.5912(3) 0.2681(6) 0.178(5) Uani 1 1 d . . . . .
H6A H 0.216175 0.559513 0.242956 0.268 Uiso 1 1 calc R U . . .
H6B H 0.238441 0.641531 0.256618 0.268 Uiso 1 1 calc R U . . .
H6C H 0.242611 0.583832 0.317660 0.268 Uiso 1 1 calc R U . . .
C14 C 0.3202(2) 0.3478(2) 0.10354(19) 0.0651(9) Uani 1 1 d . . . . .
H14 H 0.291555 0.383520 0.082240 0.078 Uiso 1 1 calc R U . . .
C13 C 0.3804(3) 0.3239(3) 0.0688(2) 0.0764(12) Uani 1 1 d . . . . .
H13 H 0.392744 0.343720 0.025417 0.092 Uiso 1 1 calc R U . . .
C12 C 0.4226(2) 0.2703(2) 0.0988(2) 0.0714(10) Uani 1 1 d . . . . .
H12 H 0.463523 0.252723 0.075733 0.086 Uiso 1 1 calc R U . . .
C15 C 0.34168(17) 0.27053(16) 0.19541(18) 0.0518(7) Uani 1 1 d . . . . .
H15 H 0.328222 0.252054 0.239041 0.062 Uiso 1 1 calc R U . . .
F2 F 0.0182(3) 0.2262(3) 0.1437(2) 0.190(3) Uani 1 1 d . . . . .
F13 F 0.1429(3) 0.5747(3) 0.0835(3) 0.1524(14) Uani 1 1 d . U . . .
F14 F 0.1993(6) 0.5350(8) 0.0265(9) 0.168(7) Uani 0.5 1 d . . P A 1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O1 2.119(3) . ?
Mn1 O3 2.132(3) . ?
Mn1 O5 2.135(2) . ?
Mn1 O4 2.177(3) . ?
Mn1 O2 2.187(2) . ?
Mn1 N3 2.272(3) . ?
F1 C16 1.296(6) . ?
F3 C16 1.267(7) . ?
F4 C20 1.298(6) . ?
F5 F14 0.92(2) . ?
F5 C20 1.277(12) . ?
O4 C22 1.232(5) . ?
F11 C25 1.265(7) . ?
F12 C25 1.315(8) . ?
F7 C21 1.307(9) . ?
F9 C21 1.330(10) . ?
F8 C21 1.223(7) . ?
O3 C19 1.247(5) . ?
O2 C17 1.233(4) . ?
O5 C24 1.250(5) . ?
F10 C25 1.276(7) . ?
N2 C10 1.261(5) . ?
N2 C3 1.460(5) . ?
O1 N1 1.274(4) . ?
C8 C5 1.518(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
N3 C14 1.329(5) . ?
N3 C15 1.340(4) . ?
C19 C18 1.374(6) . ?
C19 C20 1.531(7) . ?
C18 C17 1.383(6) . ?
C18 H18 0.9300 . ?
C17 C16 1.532(6) . ?
C16 F2 1.267(6) . ?
C20 F14 1.206(11) . ?
C20 F13 1.344(8) . ?
C22 C23 1.395(7) . ?
C22 C21 1.530(7) . ?
C23 C24 1.368(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.521(7) . ?
N1 C1 1.472(5) . ?
N1 C5 1.488(4) . ?
C1 C7 1.514(10) . ?
C1 C6 1.522(9) . ?
C1 C2 1.534(6) . ?
C2 C3 1.494(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.499(6) . ?
C3 H3 0.9800 . ?
C10 C11 1.472(5) 4_655 ?
C10 H10 0.9300 . ?
C11 C12 1.382(5) . ?
C11 C15 1.383(5) . ?
C4 C5 1.537(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C9 1.495(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C14 C13 1.362(6) . ?
C14 H14 0.9300 . ?
C13 C12 1.371(6) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?
C15 H15 0.9300 . ?

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 O3 92.32(12) . . ?
O1 Mn1 O5 91.19(12) . . ?
O3 Mn1 O5 173.48(11) . . ?
O1 Mn1 O4 86.56(12) . . ?
O3 Mn1 O4 92.54(12) . . ?
O5 Mn1 O4 82.18(11) . . ?
O1 Mn1 O2 172.63(13) . . ?
O3 Mn1 O2 81.53(10) . . ?
O5 Mn1 O2 95.33(10) . . ?
O4 Mn1 O2 97.71(11) . . ?
O1 Mn1 N3 86.76(12) . . ?
O3 Mn1 N3 95.21(11) . . ?
O5 Mn1 N3 90.47(10) . . ?
O4 Mn1 N3 169.96(10) . . ?
O2 Mn1 N3 89.74(11) . . ?
F14 F5 C20 64.2(12) . . ?
C22 O4 Mn1 125.5(3) . . ?
C19 O3 Mn1 130.4(3) . . ?
C17 O2 Mn1 128.8(3) . . ?
C24 O5 Mn1 126.0(3) . . ?
C10 N2 C3 118.1(4) . . ?
N1 O1 Mn1 164.7(3) . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 N3 C15 117.2(3) . . ?
C14 N3 Mn1 121.5(2) . . ?
C15 N3 Mn1 120.5(2) . . ?
O3 C19 C18 127.9(4) . . ?
O3 C19 C20 113.8(4) . . ?
C18 C19 C20 118.2(4) . . ?
C19 C18 C17 122.6(4) . . ?
C19 C18 H18 118.7 . . ?
C17 C18 H18 118.7 . . ?
O2 C17 C18 128.2(4) . . ?
O2 C17 C16 114.3(4) . . ?
C18 C17 C16 117.5(4) . . ?
F2 C16 F3 105.7(6) . . ?
F2 C16 F1 105.2(5) . . ?
F3 C16 F1 107.3(5) . . ?
F2 C16 C17 113.1(4) . . ?
F3 C16 C17 111.1(5) . . ?
F1 C16 C17 113.8(4) . . ?
F14 C20 F5 43.6(9) . . ?
F14 C20 F4 125.4(8) . . ?
F5 C20 F4 103.5(9) . . ?
F14 C20 F13 81.4(9) . . ?
F5 C20 F13 123.1(8) . . ?
F4 C20 F13 97.3(5) . . ?
F14 C20 C19 118.3(8) . . ?
F5 C20 C19 109.4(7) . . ?
F4 C20 C19 113.5(5) . . ?
F13 C20 C19 109.4(5) . . ?
O4 C22 C23 128.4(4) . . ?
O4 C22 C21 116.2(5) . . ?
C23 C22 C21 115.5(5) . . ?
C24 C23 C22 121.8(4) . . ?
C24 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?
O5 C24 C23 129.3(4) . . ?
O5 C24 C25 114.6(4) . . ?
C23 C24 C25 116.1(4) . . ?
F11 C25 F10 106.1(6) . . ?
F11 C25 F12 104.0(6) . . ?
F10 C25 F12 105.4(7) . . ?
F11 C25 C24 112.6(6) . . ?
F10 C25 C24 114.7(5) . . ?
F12 C25 C24 113.2(4) . . ?
F8 C21 F7 109.4(8) . . ?
F8 C21 F9 110.0(7) . . ?
F7 C21 F9 98.3(5) . . ?
F8 C21 C22 115.9(5) . . ?
F7 C21 C22 112.7(6) . . ?
F9 C21 C22 109.1(7) . . ?
O1 N1 C1 118.1(3) . . ?
O1 N1 C5 115.4(3) . . ?
C1 N1 C5 125.1(3) . . ?
N1 C1 C7 108.7(5) . . ?
N1 C1 C6 107.0(5) . . ?
C7 C1 C6 111.4(6) . . ?
N1 C1 C2 109.2(4) . . ?
C7 C1 C2 111.6(5) . . ?
C6 C1 C2 109.0(5) . . ?
C3 C2 C1 115.4(4) . . ?
C3 C2 H2A 108.4 . . ?
C1 C2 H2A 108.4 . . ?
C3 C2 H2B 108.4 . . ?
C1 C2 H2B 108.4 . . ?
H2A C2 H2B 107.5 . . ?
N2 C3 C2 109.0(3) . . ?
N2 C3 C4 108.2(3) . . ?
C2 C3 C4 108.0(3) . . ?
N2 C3 H3 110.5 . . ?
C2 C3 H3 110.5 . . ?
C4 C3 H3 110.5 . . ?
N2 C10 C11 121.0(4) . 4_655 ?
N2 C10 H10 119.5 . . ?
C11 C10 H10 119.5 4_655 . ?
C12 C11 C15 117.8(3) . . ?
C12 C11 C10 122.4(3) . 4_645 ?
C15 C11 C10 119.8(3) . 4_645 ?
C3 C4 C5 114.1(3) . . ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
N1 C5 C9 110.3(4) . . ?
N1 C5 C8 107.6(3) . . ?
C9 C5 C8 108.3(4) . . ?
N1 C5 C4 108.8(3) . . ?
C9 C5 C4 111.9(3) . . ?
C8 C5 C4 109.9(3) . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C14 C13 123.6(3) . . ?
N3 C14 H14 118.2 . . ?
C13 C14 H14 118.2 . . ?
C14 C13 C12 119.0(4) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C12 C11 119.2(4) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
N3 C15 C11 123.2(3) . . ?
N3 C15 H15 118.4 . . ?
C11 C15 H15 118.4 . . ?
F5 F14 C20 72.2(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Mn1 O3 C19 C18 3.7(6) . . . . ?
Mn1 O3 C19 C20 -172.9(3) . . . . ?
O3 C19 C18 C17 1.4(7) . . . . ?
C20 C19 C18 C17 177.8(4) . . . . ?
Mn1 O2 C17 C18 -7.5(6) . . . . ?
Mn1 O2 C17 C16 173.0(3) . . . . ?
C19 C18 C17 O2 0.9(7) . . . . ?
C19 C18 C17 C16 -179.7(4) . . . . ?
O2 C17 C16 F2 38.7(7) . . . . ?
C18 C17 C16 F2 -140.8(5) . . . . ?
O2 C17 C16 F3 -80.0(6) . . . . ?
C18 C17 C16 F3 100.6(6) . . . . ?
O2 C17 C16 F1 158.7(5) . . . . ?
C18 C17 C16 F1 -20.7(7) . . . . ?
F14 F5 C20 F4 127.7(15) . . . . ?
F14 F5 C20 F13 19.4(18) . . . . ?
F14 F5 C20 C19 -111.1(14) . . . . ?
O3 C19 C20 F14 50.6(12) . . . . ?
C18 C19 C20 F14 -126.3(11) . . . . ?
O3 C19 C20 F5 97.5(10) . . . . ?
C18 C19 C20 F5 -79.4(10) . . . . ?
O3 C19 C20 F4 -147.4(5) . . . . ?
C18 C19 C20 F4 35.7(7) . . . . ?
O3 C19 C20 F13 -40.0(6) . . . . ?
C18 C19 C20 F13 143.1(5) . . . . ?
Mn1 O4 C22 C23 -19.5(7) . . . . ?
Mn1 O4 C22 C21 161.4(4) . . . . ?
O4 C22 C23 C24 -0.3(8) . . . . ?
C21 C22 C23 C24 178.8(5) . . . . ?
Mn1 O5 C24 C23 17.6(6) . . . . ?
Mn1 O5 C24 C25 -161.8(3) . . . . ?
C22 C23 C24 O5 1.6(8) . . . . ?
C22 C23 C24 C25 -179.0(5) . . . . ?
O5 C24 C25 F11 -84.1(7) . . . . ?
C23 C24 C25 F11 96.4(6) . . . . ?
O5 C24 C25 F10 154.5(6) . . . . ?
C23 C24 C25 F10 -25.0(8) . . . . ?
O5 C24 C25 F12 33.5(7) . . . . ?
C23 C24 C25 F12 -146.0(6) . . . . ?
O4 C22 C21 F8 -139.0(8) . . . . ?
C23 C22 C21 F8 41.8(11) . . . . ?
O4 C22 C21 F7 -11.9(9) . . . . ?
C23 C22 C21 F7 168.9(6) . . . . ?
O4 C22 C21 F9 96.2(8) . . . . ?
C23 C22 C21 F9 -83.0(7) . . . . ?
Mn1 O1 N1 C1 48.2(11) . . . . ?
Mn1 O1 N1 C5 -118.9(9) . . . . ?
O1 N1 C1 C7 -78.4(5) . . . . ?
C5 N1 C1 C7 87.3(5) . . . . ?
O1 N1 C1 C6 41.9(7) . . . . ?
C5 N1 C1 C6 -152.4(5) . . . . ?
O1 N1 C1 C2 159.7(4) . . . . ?
C5 N1 C1 C2 -34.6(7) . . . . ?
N1 C1 C2 C3 44.6(7) . . . . ?
C7 C1 C2 C3 -75.5(6) . . . . ?
C6 C1 C2 C3 161.1(6) . . . . ?
C10 N2 C3 C2 -128.2(5) . . . . ?
C10 N2 C3 C4 114.5(4) . . . . ?
C1 C2 C3 N2 -176.0(5) . . . . ?
C1 C2 C3 C4 -58.6(6) . . . . ?
C3 N2 C10 C11 179.8(3) . . . 4_655 ?
N2 C3 C4 C5 177.9(3) . . . . ?
C2 C3 C4 C5 60.0(5) . . . . ?
O1 N1 C5 C9 79.2(4) . . . . ?
C1 N1 C5 C9 -86.8(5) . . . . ?
O1 N1 C5 C8 -38.7(5) . . . . ?
C1 N1 C5 C8 155.3(5) . . . . ?
O1 N1 C5 C4 -157.7(3) . . . . ?
C1 N1 C5 C4 36.2(6) . . . . ?
C3 C4 C5 N1 -47.4(5) . . . . ?
C3 C4 C5 C9 74.8(5) . . . . ?
C3 C4 C5 C8 -165.0(4) . . . . ?
C15 N3 C14 C13 -1.1(6) . . . . ?
Mn1 N3 C14 C13 169.0(3) . . . . ?
N3 C14 C13 C12 1.2(7) . . . . ?
C14 C13 C12 C11 -0.9(7) . . . . ?
C15 C11 C12 C13 0.5(6) . . . . ?
C10 C11 C12 C13 -178.5(4) 4_645 . . . ?
C14 N3 C15 C11 0.6(5) . . . . ?
Mn1 N3 C15 C11 -169.5(2) . . . . ?
C12 C11 C15 N3 -0.4(5) . . . . ?
C10 C11 C15 N3 178.6(3) 4_645 . . . ?
F4 C20 F14 F5 -70.7(18) . . . . ?
F13 C20 F14 F5 -163.6(15) . . . . ?
C19 C20 F14 F5 88.9(16) . . . . ?

_refine_diff_density_max         0.678
_refine_diff_density_min         -1.016
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_8
_audit_block_doi                 10.5517/ccdc.csd.cc1yv4xv
_database_code_depnum_ccdc_archive 'CCDC 1812598'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/c8ce00061a 2018
_audit_update_record             
;
2018-04-03 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H24 F12 Mn N3 O5'
_chemical_formula_weight         729.41

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'
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      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                   9.8814(7)
_cell_length_b                   14.4685(11)
_cell_length_c                   23.2516(17)
_cell_angle_alpha                90
_cell_angle_beta                 100.481(2)
_cell_angle_gamma                90
_cell_volume                     3268.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9895
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      28.15

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.509
_shelx_estimated_absorpt_T_min   0.905
_shelx_estimated_absorpt_T_max   0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.793
_exptl_absorpt_correction_T_max  0.850
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            63692
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.802
_diffrn_reflns_theta_max         28.328
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8029
_reflns_number_gt                6178
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1064P)²+2.1484P] 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         8029
_refine_ls_number_parameters     428
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.1960
_refine_ls_wR_factor_gt          0.1801
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.076
_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
O5 O 0.68979(19) 0.25233(14) 0.48148(9) 0.0527(4) Uani 1 1 d . . . . .
Mn1 Mn 0.80838(4) 0.16028(3) 0.43754(2) 0.04182(14) Uani 1 1 d . . . . .
C11 C 0.6027(2) 0.00171(15) 0.42761(10) 0.0388(5) Uani 1 1 d . . . . .
C3 C 0.5618(3) 0.19372(18) 0.31792(11) 0.0467(6) Uani 1 1 d . . . . .
H3 H 0.474169 0.168586 0.297284 0.056 Uiso 1 1 calc R U . . .
N3 N 0.7233(2) 0.02599(14) 0.46133(9) 0.0414(4) Uani 1 1 d . . . . .
N2 N 0.6154(2) 0.13613(14) 0.36951(9) 0.0412(4) Uani 1 1 d . . . . .
C10 C 0.5507(3) 0.06333(16) 0.37794(10) 0.0420(5) Uani 1 1 d . . . . .
H10 H 0.469611 0.048504 0.352552 0.050 Uiso 1 1 calc R U . . .
C2 C 0.6661(3) 0.1938(2) 0.27815(12) 0.0532(6) Uani 1 1 d . . . . .
H2A H 0.678109 0.130992 0.265385 0.064 Uiso 1 1 calc R U . . .
H2B H 0.753820 0.214512 0.300149 0.064 Uiso 1 1 calc R U . . .
O1 O 0.5740(4) 0.41015(18) 0.20336(11) 0.0908(9) Uani 1 1 d . . . . .
C12 C 0.5308(3) -0.07638(18) 0.43862(12) 0.0493(6) Uani 1 1 d . . . . .
H12 H 0.447496 -0.091222 0.414811 0.059 Uiso 1 1 calc R U . . .
C15 C 0.7742(3) -0.0288(2) 0.50574(13) 0.0552(7) Uani 1 1 d . . . . .
H15 H 0.857846 -0.013141 0.529004 0.066 Uiso 1 1 calc R U . . .
C19 C 0.7406(3) 0.3102(2) 0.51930(13) 0.0541(6) Uani 1 1 d . . . . .
O4 O 0.9487(2) 0.16792(15) 0.52005(10) 0.0629(5) Uani 1 1 d . . . . .
O2 O 0.8967(3) 0.28604(15) 0.41011(11) 0.0685(6) Uani 1 1 d . . . . .
N1 N 0.5815(3) 0.34627(17) 0.24215(11) 0.0612(7) Uani 1 1 d . . . . .
C17 C 0.9592(3) 0.2352(3) 0.55408(14) 0.0658(8) Uani 1 1 d . . . . .
C14 C 0.7081(4) -0.1082(2) 0.51895(14) 0.0628(8) Uani 1 1 d . . . . .
H14 H 0.747412 -0.145118 0.550327 0.075 Uiso 1 1 calc R U . . .
C13 C 0.5847(4) -0.1320(2) 0.48548(14) 0.0604(7) Uani 1 1 d . . . . .
H13 H 0.537888 -0.184505 0.494071 0.072 Uiso 1 1 calc R U . . .
C18 C 0.8673(4) 0.3075(3) 0.55566(14) 0.0674(8) Uani 1 1 d . . . . .
H18 H 0.892034 0.355532 0.582073 0.081 Uiso 1 1 calc R U . . .
C4 C 0.5415(4) 0.2909(2) 0.33789(13) 0.0617(8) Uani 1 1 d . . . . .
H4A H 0.627266 0.312544 0.361099 0.074 Uiso 1 1 calc R U . . .
H4B H 0.473044 0.290183 0.362942 0.074 Uiso 1 1 calc R U . . .
C1 C 0.6264(4) 0.2558(2) 0.22395(12) 0.0609(7) Uani 1 1 d . . . . .
C5 C 0.4957(4) 0.3593(2) 0.28770(16) 0.0741(10) Uani 1 1 d . . . . .
C24 C 1.0179(3) 0.1392(3) 0.35345(14) 0.0622(8) Uani 1 1 d . . . . .
C23 C 1.0464(4) 0.2310(3) 0.34980(16) 0.0741(9) Uani 1 1 d . . . . .
H23 H 1.108711 0.249803 0.326611 0.089 Uiso 1 1 calc R U . . .
C22 C 0.9851(4) 0.2970(3) 0.37960(17) 0.0736(9) Uani 1 1 d . . . . .
F5 F 0.6798(3) 0.4409(2) 0.57120(16) 0.1381(13) Uani 1 1 d . . . . .
C20 C 0.6477(4) 0.3922(3) 0.52346(19) 0.0775(10) Uani 1 1 d . . . . .
C7 C 0.5145(6) 0.2115(3) 0.17859(15) 0.0972(15) Uani 1 1 d . . . . .
H7A H 0.439762 0.192240 0.197032 0.146 Uiso 1 1 calc R U . . .
H7B H 0.551528 0.158815 0.161721 0.146 Uiso 1 1 calc R U . . .
H7C H 0.481525 0.255611 0.148432 0.146 Uiso 1 1 calc R U . . .
F6 F 0.5217(3) 0.3652(2) 0.5264(2) 0.1580(18) Uani 1 1 d . . . . .
C25 C 1.0829(5) 0.0720(4) 0.3159(2) 0.1001(15) Uani 1 1 d . . . . .
C9 C 0.3431(5) 0.3467(4) 0.2600(3) 0.115(2) Uani 1 1 d . . . . .
H9A H 0.286469 0.372947 0.285278 0.173 Uiso 1 1 calc R U . . .
H9B H 0.323020 0.282040 0.254748 0.173 Uiso 1 1 calc R U . . .
H9C H 0.324669 0.377322 0.222783 0.173 Uiso 1 1 calc R U . . .
F4 F 1.0924(4) 0.2861(5) 0.64303(18) 0.236(3) Uani 1 1 d . . . . .
F11 F 0.9978(5) 0.0353(5) 0.2774(2) 0.247(3) Uani 1 1 d . . . . .
C6 C 0.7543(5) 0.2716(4) 0.19727(19) 0.1011(15) Uani 1 1 d . . . . .
H6A H 0.730690 0.308304 0.162499 0.152 Uiso 1 1 calc R U . . .
H6B H 0.790316 0.213143 0.187566 0.152 Uiso 1 1 calc R U . . .
H6C H 0.822624 0.303312 0.224925 0.152 Uiso 1 1 calc R U . . .
F7 F 0.6396(6) 0.4457(3) 0.48078(19) 0.203(3) Uani 1 1 d . . . . .
C8 C 0.5223(8) 0.4566(3) 0.3109(2) 0.129(2) Uani 1 1 d . . . . .
H8A H 0.619107 0.464841 0.324771 0.193 Uiso 1 1 calc R U . . .
H8B H 0.473357 0.466632 0.342397 0.193 Uiso 1 1 calc R U . . .
H8C H 0.491272 0.500105 0.280096 0.193 Uiso 1 1 calc R U . . .
F12 F 1.1445(6) 0.0043(3) 0.3456(2) 0.193(2) Uani 1 1 d . . . . .
F13 F 1.1775(6) 0.1056(4) 0.2918(3) 0.218(3) Uani 1 1 d . . . . .
O3 O 0.9434(2) 0.10010(14) 0.38459(9) 0.0588(5) Uani 1 1 d . . . . .
F8 F 1.0235(10) 0.4469(4) 0.4200(3) 0.204(4) Uani 0.75 1 d . . P . .
F2 F 1.1464(7) 0.1591(4) 0.6111(2) 0.228(3) Uani 1 1 d . . . . .
C21 C 1.0212(9) 0.4004(5) 0.3732(4) 0.152(3) Uani 1 1 d . . . . .
C16 C 1.0895(5) 0.2346(6) 0.6003(3) 0.128(2) Uani 1 1 d . . . . .
F3 F 1.1914(4) 0.2696(7) 0.5750(3) 0.240(3) Uani 1 1 d . . . . .
F1 F 1.1641(11) 0.3997(7) 0.3832(6) 0.262(4) Uani 0.75 1 d . U P . .
F14 F 1.0755(11) 0.4214(4) 0.3328(4) 0.208(4) Uani 0.75 1 d . . P . .
F16 F 0.9107(11) 0.4455(5) 0.3453(7) 0.300(8) Uani 0.75 1 d . . 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
O5 C19 1.251(3) . ?
O5 Mn1 2.1508(19) . ?
Mn1 O4 2.156(2) . ?
Mn1 O3 2.157(2) . ?
Mn1 O2 2.164(2) . ?
Mn1 N3 2.227(2) . ?
Mn1 N2 2.273(2) . ?
C11 N3 1.349(3) . ?
C11 C12 1.383(3) . ?
C11 C10 1.475(3) . ?
C3 N2 1.477(3) . ?
C3 C2 1.505(4) . ?
C3 C4 1.505(4) . ?
N3 C15 1.326(3) . ?
N2 C10 1.265(3) . ?
C2 C1 1.538(4) . ?
O1 N1 1.284(3) . ?
C12 C13 1.381(4) . ?
C15 C14 1.383(4) . ?
C19 C18 1.377(5) . ?
C19 C20 1.513(5) . ?
O4 C17 1.247(4) . ?
O2 C22 1.231(4) . ?
N1 C1 1.470(4) . ?
N1 C5 1.484(5) . ?
C17 C18 1.390(5) . ?
C17 C16 1.519(5) . ?
C14 C13 1.366(5) . ?
C4 C5 1.535(4) . ?
C1 C6 1.523(6) . ?
C1 C7 1.524(5) . ?
C5 C8 1.513(6) . ?
C5 C9 1.538(6) . ?
C24 O3 1.257(4) . ?
C24 C23 1.365(5) . ?
C24 C25 1.524(5) . ?
C23 C22 1.382(6) . ?
C22 C21 1.552(7) . ?
F5 C20 1.304(5) . ?
C20 F7 1.250(5) . ?
C20 F6 1.319(5) . ?
C25 F11 1.232(6) . ?
C25 F13 1.271(6) . ?
C25 F12 1.286(6) . ?
F4 C16 1.238(6) . ?
F8 C21 1.275(9) . ?
F2 C16 1.233(8) . ?
C21 F14 1.203(9) . ?
C21 F16 1.335(12) . ?
C21 F1 1.389(13) . ?
C16 F3 1.354(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
C19 O5 Mn1 124.35(18) . . ?
O5 Mn1 O4 82.14(8) . . ?
O5 Mn1 O3 165.51(8) . . ?
O4 Mn1 O3 99.46(9) . . ?
O5 Mn1 O2 84.43(8) . . ?
O4 Mn1 O2 89.46(10) . . ?
O3 Mn1 O2 81.18(9) . . ?
O5 Mn1 N3 99.17(8) . . ?
O4 Mn1 N3 91.97(8) . . ?
O3 Mn1 N3 95.18(8) . . ?
O2 Mn1 N3 176.27(8) . . ?
O5 Mn1 N2 88.00(7) . . ?
O4 Mn1 N2 161.77(9) . . ?
O3 Mn1 N2 93.93(8) . . ?
O2 Mn1 N2 104.86(9) . . ?
N3 Mn1 N2 74.44(7) . . ?
N3 C11 C12 122.3(2) . . ?
N3 C11 C10 116.3(2) . . ?
C12 C11 C10 121.4(2) . . ?
N2 C3 C2 108.4(2) . . ?
N2 C3 C4 108.9(2) . . ?
C2 C3 C4 109.4(2) . . ?
C15 N3 C11 117.8(2) . . ?
C15 N3 Mn1 127.46(18) . . ?
C11 N3 Mn1 114.62(15) . . ?
C10 N2 C3 118.6(2) . . ?
C10 N2 Mn1 113.79(16) . . ?
C3 N2 Mn1 127.59(16) . . ?
N2 C10 C11 120.7(2) . . ?
C3 C2 C1 113.8(2) . . ?
C13 C12 C11 119.0(3) . . ?
N3 C15 C14 122.8(3) . . ?
O5 C19 C18 128.0(3) . . ?
O5 C19 C20 113.5(3) . . ?
C18 C19 C20 118.5(3) . . ?
C17 O4 Mn1 124.8(2) . . ?
C22 O2 Mn1 130.1(2) . . ?
O1 N1 C1 114.9(3) . . ?
O1 N1 C5 116.2(3) . . ?
C1 N1 C5 124.1(2) . . ?
O4 C17 C18 128.7(3) . . ?
O4 C17 C16 114.0(4) . . ?
C18 C17 C16 117.3(3) . . ?
C13 C14 C15 119.4(3) . . ?
C14 C13 C12 118.6(3) . . ?
C19 C18 C17 122.0(3) . . ?
C3 C4 C5 113.9(3) . . ?
N1 C1 C6 107.5(3) . . ?
N1 C1 C7 110.7(3) . . ?
C6 C1 C7 109.5(3) . . ?
N1 C1 C2 109.2(2) . . ?
C6 C1 C2 108.3(3) . . ?
C7 C1 C2 111.5(3) . . ?
N1 C5 C8 106.7(4) . . ?
N1 C5 C4 109.4(3) . . ?
C8 C5 C4 108.8(3) . . ?
N1 C5 C9 109.3(4) . . ?
C8 C5 C9 110.7(4) . . ?
C4 C5 C9 111.9(3) . . ?
O3 C24 C23 128.5(3) . . ?
O3 C24 C25 113.3(4) . . ?
C23 C24 C25 118.2(4) . . ?
C24 C23 C22 121.8(3) . . ?
O2 C22 C23 128.4(3) . . ?
O2 C22 C21 112.3(4) . . ?
C23 C22 C21 119.2(4) . . ?
F7 C20 F5 108.1(4) . . ?
F7 C20 F6 107.4(5) . . ?
F5 C20 F6 101.7(4) . . ?
F7 C20 C19 112.8(3) . . ?
F5 C20 C19 114.9(3) . . ?
F6 C20 C19 111.2(3) . . ?
F11 C25 F13 107.7(5) . . ?
F11 C25 F12 104.9(6) . . ?
F13 C25 F12 102.4(5) . . ?
F11 C25 C24 112.9(4) . . ?
F13 C25 C24 115.4(5) . . ?
F12 C25 C24 112.6(4) . . ?
C24 O3 Mn1 129.5(2) . . ?
F14 C21 F8 126.3(7) . . ?
F14 C21 F16 86.4(10) . . ?
F8 C21 F16 92.5(9) . . ?
F14 C21 F1 63.1(6) . . ?
F8 C21 F1 90.1(9) . . ?
F16 C21 F1 143.3(8) . . ?
F14 C21 C22 117.5(7) . . ?
F8 C21 C22 113.3(6) . . ?
F16 C21 C22 109.6(6) . . ?
F1 C21 C22 102.8(8) . . ?
F2 C16 F4 115.2(7) . . ?
F2 C16 F3 94.1(6) . . ?
F4 C16 F3 102.3(6) . . ?
F2 C16 C17 116.5(5) . . ?
F4 C16 C17 117.2(4) . . ?
F3 C16 C17 107.0(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 C11 N3 C15 1.2(4) . . . . ?
C10 C11 N3 C15 -178.8(2) . . . . ?
C12 C11 N3 Mn1 -175.64(19) . . . . ?
C10 C11 N3 Mn1 4.3(3) . . . . ?
C2 C3 N2 C10 -116.1(3) . . . . ?
C4 C3 N2 C10 124.9(3) . . . . ?
C2 C3 N2 Mn1 62.6(3) . . . . ?
C4 C3 N2 Mn1 -56.4(3) . . . . ?
C3 N2 C10 C11 177.8(2) . . . . ?
Mn1 N2 C10 C11 -1.0(3) . . . . ?
N3 C11 C10 N2 -2.2(3) . . . . ?
C12 C11 C10 N2 177.7(2) . . . . ?
N2 C3 C2 C1 -176.9(2) . . . . ?
C4 C3 C2 C1 -58.3(3) . . . . ?
N3 C11 C12 C13 -0.5(4) . . . . ?
C10 C11 C12 C13 179.6(3) . . . . ?
C11 N3 C15 C14 -0.8(4) . . . . ?
Mn1 N3 C15 C14 175.6(2) . . . . ?
Mn1 O5 C19 C18 -25.6(4) . . . . ?
Mn1 O5 C19 C20 153.9(2) . . . . ?
Mn1 O4 C17 C18 17.4(5) . . . . ?
Mn1 O4 C17 C16 -164.3(4) . . . . ?
N3 C15 C14 C13 -0.4(5) . . . . ?
C15 C14 C13 C12 1.2(5) . . . . ?
C11 C12 C13 C14 -0.7(5) . . . . ?
O5 C19 C18 C17 0.2(6) . . . . ?
C20 C19 C18 C17 -179.2(3) . . . . ?
O4 C17 C18 C19 4.4(6) . . . . ?
C16 C17 C18 C19 -173.9(5) . . . . ?
N2 C3 C4 C5 175.9(3) . . . . ?
C2 C3 C4 C5 57.6(4) . . . . ?
O1 N1 C1 C6 48.4(4) . . . . ?
C5 N1 C1 C6 -157.0(3) . . . . ?
O1 N1 C1 C7 -71.1(4) . . . . ?
C5 N1 C1 C7 83.4(4) . . . . ?
O1 N1 C1 C2 165.7(3) . . . . ?
C5 N1 C1 C2 -39.8(4) . . . . ?
C3 C2 C1 N1 47.4(4) . . . . ?
C3 C2 C1 C6 164.1(3) . . . . ?
C3 C2 C1 C7 -75.3(4) . . . . ?
O1 N1 C5 C8 -49.1(4) . . . . ?
C1 N1 C5 C8 156.7(3) . . . . ?
O1 N1 C5 C4 -166.6(3) . . . . ?
C1 N1 C5 C4 39.2(5) . . . . ?
O1 N1 C5 C9 70.6(4) . . . . ?
C1 N1 C5 C9 -83.6(4) . . . . ?
C3 C4 C5 N1 -46.0(4) . . . . ?
C3 C4 C5 C8 -162.2(4) . . . . ?
C3 C4 C5 C9 75.3(4) . . . . ?
O3 C24 C23 C22 -4.3(6) . . . . ?
C25 C24 C23 C22 175.9(4) . . . . ?
Mn1 O2 C22 C23 5.7(6) . . . . ?
Mn1 O2 C22 C21 -177.7(5) . . . . ?
C24 C23 C22 O2 -3.3(7) . . . . ?
C24 C23 C22 C21 -179.6(6) . . . . ?
O5 C19 C20 F7 -72.3(5) . . . . ?
C18 C19 C20 F7 107.2(5) . . . . ?
O5 C19 C20 F5 163.1(3) . . . . ?
C18 C19 C20 F5 -17.3(5) . . . . ?
O5 C19 C20 F6 48.4(5) . . . . ?
C18 C19 C20 F6 -132.1(4) . . . . ?
O3 C24 C25 F11 67.6(7) . . . . ?
C23 C24 C25 F11 -112.6(6) . . . . ?
O3 C24 C25 F13 -168.0(5) . . . . ?
C23 C24 C25 F13 11.8(7) . . . . ?
O3 C24 C25 F12 -50.9(6) . . . . ?
C23 C24 C25 F12 128.9(5) . . . . ?
C23 C24 O3 Mn1 8.4(5) . . . . ?
C25 C24 O3 Mn1 -171.8(3) . . . . ?
O2 C22 C21 F14 -160.0(9) . . . . ?
C23 C22 C21 F14 16.9(13) . . . . ?
O2 C22 C21 F8 38.1(11) . . . . ?
C23 C22 C21 F8 -145.1(8) . . . . ?
O2 C22 C21 F16 -63.7(11) . . . . ?
C23 C22 C21 F16 113.2(10) . . . . ?
O2 C22 C21 F1 133.8(7) . . . . ?
C23 C22 C21 F1 -49.3(10) . . . . ?
O4 C17 C16 F2 -21.5(10) . . . . ?
C18 C17 C16 F2 157.1(7) . . . . ?
O4 C17 C16 F4 -163.8(7) . . . . ?
C18 C17 C16 F4 14.7(10) . . . . ?
O4 C17 C16 F3 82.1(7) . . . . ?
C18 C17 C16 F3 -99.3(6) . . . . ?

_refine_diff_density_max         0.986
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_6
_audit_block_doi                 10.5517/ccdc.csd.cc1yv4zx
_database_code_depnum_ccdc_archive 'CCDC 1812600'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/c8ce00061a 2018
_audit_update_record             
;
2018-04-03 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H46 F12 Mn N6 O6'
_chemical_formula_weight         989.77

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'
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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   16.6043(6)
_cell_length_b                   26.0628(11)
_cell_length_c                   10.8332(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4688.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9894
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      28.18

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             2036
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.379
_shelx_estimated_absorpt_T_min   0.827
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8554
_exptl_absorpt_correction_T_max  0.9203
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39423
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.575
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4213
_reflns_number_gt                3303
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1474P)²+10.8682P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4213
_refine_ls_number_parameters     338
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.1058
_refine_ls_R_factor_gt           0.0876
_refine_ls_wR_factor_ref         0.2650
_refine_ls_wR_factor_gt          0.2445
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.107
_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 0.17347(5) 0.250000 -0.02215(8) 0.0383(3) Uani 1 2 d S T P . .
N3 N 0.0997(2) 0.18869(14) 0.0700(3) 0.0415(8) Uani 1 1 d . . . . .
O2 O 0.2619(3) 0.250000 0.1225(5) 0.0565(12) Uani 1 2 d S T P . .
O4 O 0.1178(3) 0.250000 -0.2005(4) 0.0547(12) Uani 1 2 d S T P . .
N1 N 0.1409(2) -0.00734(15) 0.7400(3) 0.0462(9) Uani 1 1 d . . . . .
N2 N 0.0893(3) 0.07154(16) 0.4080(4) 0.0518(10) Uani 1 1 d . . . . .
C5 C 0.0951(3) 0.04152(18) 0.7520(4) 0.0484(11) Uani 1 1 d . . . . .
C12 C 0.0133(3) 0.11221(18) 0.1880(4) 0.0497(11) Uani 1 1 d . . . . .
H12 H -0.015986 0.086588 0.227512 0.060 Uiso 1 1 calc R U . . .
O1 O 0.1569(3) -0.03067(16) 0.8416(3) 0.0681(11) Uani 1 1 d . . . . .
C14 C 0.0297(3) 0.17140(18) 0.0244(4) 0.0466(11) Uani 1 1 d . . . . .
H14 H 0.010321 0.185797 -0.048347 0.056 Uiso 1 1 calc R U . . .
C11 C 0.0856(3) 0.12938(16) 0.2378(4) 0.0417(10) Uani 1 1 d . . . . .
C2 C 0.1548(3) 0.0001(2) 0.5136(4) 0.0492(11) Uani 1 1 d . . . . .
H2A H 0.194248 -0.002310 0.447822 0.059 Uiso 1 1 calc R U . . .
H2B H 0.108957 -0.020877 0.490290 0.059 Uiso 1 1 calc R U . . .
O3 O 0.2536(2) 0.30725(13) -0.1047(3) 0.0543(9) Uani 1 1 d . . . . .
C1 C 0.1915(3) -0.02181(19) 0.6315(4) 0.0465(11) Uani 1 1 d . . . . .
C3 C 0.1275(3) 0.05521(18) 0.5244(4) 0.0459(11) Uani 1 1 d . . . . .
H3 H 0.173327 0.077483 0.543956 0.055 Uiso 1 1 calc R U . . .
C10 C 0.1197(3) 0.10910(18) 0.3532(4) 0.0480(11) Uani 1 1 d . . . . .
H10 H 0.165256 0.124637 0.386374 0.058 Uiso 1 1 calc R U . . .
C4 C 0.0649(3) 0.0582(2) 0.6253(4) 0.0523(12) Uani 1 1 d . . . . .
H4A H 0.019452 0.036830 0.602492 0.063 Uiso 1 1 calc R U . . .
H4B H 0.045675 0.093315 0.630932 0.063 Uiso 1 1 calc R U . . .
C15 C 0.1262(3) 0.16785(17) 0.1751(4) 0.0448(10) Uani 1 1 d . . . . .
H15 H 0.174395 0.179808 0.207954 0.054 Uiso 1 1 calc R U . . .
C7 C 0.2776(3) -0.0019(2) 0.6503(5) 0.0634(14) Uani 1 1 d . . . . .
H7A H 0.276935 0.034907 0.654290 0.095 Uiso 1 1 calc R U . . .
H7B H 0.310735 -0.012653 0.582424 0.095 Uiso 1 1 calc R U . . .
H7C H 0.298991 -0.015449 0.725853 0.095 Uiso 1 1 calc R U . . .
C13 C -0.0147(3) 0.13338(19) 0.0801(5) 0.0524(12) Uani 1 1 d . . . . .
H13 H -0.062806 0.122196 0.045313 0.063 Uiso 1 1 calc R U . . .
C6 C 0.1925(4) -0.0800(2) 0.6242(6) 0.0659(15) Uani 1 1 d . . . . .
H6A H 0.213837 -0.093798 0.699653 0.099 Uiso 1 1 calc R U . . .
H6B H 0.225709 -0.090638 0.556293 0.099 Uiso 1 1 calc R U . . .
H6C H 0.138663 -0.092454 0.612163 0.099 Uiso 1 1 calc R U . . .
C8 C 0.0227(4) 0.0323(3) 0.8361(6) 0.0731(17) Uani 1 1 d . . . . .
H8A H -0.010032 0.005365 0.802381 0.110 Uiso 1 1 calc R U . . .
H8B H -0.008573 0.063214 0.841959 0.110 Uiso 1 1 calc R U . . .
H8C H 0.041088 0.022593 0.916767 0.110 Uiso 1 1 calc R U . . .
C9 C 0.1502(4) 0.0822(2) 0.8103(5) 0.0698(15) Uani 1 1 d . . . . .
H9A H 0.171049 0.069475 0.887083 0.105 Uiso 1 1 calc R U . . .
H9B H 0.119853 0.112950 0.825086 0.105 Uiso 1 1 calc R U . . .
H9C H 0.193953 0.089557 0.755271 0.105 Uiso 1 1 calc R U . . .
C22 C 0.2252(7) 0.2887(4) -0.3143(10) 0.062(3) Uani 0.5 1 d . . P A 1
H22 H 0.239012 0.298456 -0.394101 0.075 Uiso 0.5 1 d R U P A 1
C24 C 0.1159(9) 0.250000 -0.4146(11) 0.106(4) Uani 1 2 d S T P . .
F1 F 0.4619(8) 0.250000 0.2060(11) 0.178(3) Uani 1 2 d S TU P . .
F2 F 0.3663(8) 0.250000 0.3139(12) 0.183(3) Uani 1 2 d S TU P . .
C17 C 0.3347(6) 0.2640(3) 0.1075(12) 0.061(3) Uani 0.5 1 d . . P A -1
C23 C 0.1531(6) 0.250000 -0.2984(8) 0.095(4) Uani 1 2 d S T P A 1
C20 C 0.3282(6) 0.3089(4) -0.0875(11) 0.055(3) Uani 0.5 1 d . . P A -1
C16 C 0.3877(15) 0.250000 0.205(2) 0.177(3) Uani 1 2 d S TU P . .
C19 C 0.3696(7) 0.3367(4) -0.2006(13) 0.138(4) Uani 1 1 d . U . . .
F3 F 0.3670(8) 0.2023(5) 0.2692(14) 0.160(4) Uani 0.5 1 d . U P A .
C18 C 0.3712(7) 0.2895(4) 0.0115(13) 0.071(3) Uani 0.5 1 d . . P A -1
H18 H 0.426791 0.293825 0.013170 0.086 Uiso 0.5 1 calc R U P A -1
F5 F 0.4207(7) 0.3147(4) -0.2387(13) 0.331(9) Uani 1 1 d . . . . .
F6 F 0.3624(4) 0.3830(3) -0.1802(7) 0.154(2) Uani 1 1 d . . . . .
F9 F 0.1471(10) 0.250000 -0.5128(7) 0.262(8) Uani 1 2 d S T P A .
C21 C 0.2690(6) 0.3101(4) -0.2162(10) 0.052(2) Uani 0.5 1 d . . P A 1
F10 F 0.0714(10) 0.2872(5) -0.4184(10) 0.354(9) Uani 1 1 d . . . . .
F7 F 0.3436(7) 0.3454(6) -0.3219(12) 0.259(5) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O4 2.142(5) . ?
Mn1 O2 2.147(5) . ?
Mn1 O3 2.191(3) 8_565 ?
Mn1 O3 2.191(3) . ?
Mn1 N3 2.247(4) 8_565 ?
Mn1 N3 2.247(4) . ?
N3 C15 1.336(6) . ?
N3 C14 1.341(6) . ?
O2 C17 1.274(11) . ?
O4 C23 1.211(10) . ?
N1 O1 1.285(5) . ?
N1 C5 1.488(6) . ?
N1 C1 1.494(6) . ?
N2 C10 1.252(6) . ?
N2 C3 1.474(6) . ?
C5 C4 1.525(7) . ?
C5 C8 1.528(7) . ?
C5 C9 1.535(7) . ?
C12 C13 1.374(7) . ?
C12 C11 1.391(7) . ?
C12 H12 0.9300 . ?
C14 C13 1.375(7) . ?
C14 H14 0.9300 . ?
C11 C15 1.386(6) . ?
C11 C10 1.470(6) . ?
C2 C3 1.511(7) . ?
C2 C1 1.526(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
O3 C21 1.237(10) . ?
O3 C20 1.253(11) . ?
C1 C6 1.520(7) . ?
C1 C7 1.535(7) . ?
C3 C4 1.511(7) . ?
C3 H3 0.9800 . ?
C10 H10 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C15 H15 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C13 H13 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C22 C21 1.405(16) . ?
C22 C23 1.575(13) . ?
C22 H22 0.9299 . ?
C24 F9 1.183(15) . ?
C24 F10 1.220(12) 8_565 ?
C24 F10 1.220(12) . ?
C24 C23 1.401(15) . ?
F1 C16 1.23(2) . ?
F2 C16 1.23(2) . ?
C17 C18 1.375(17) . ?
C17 C16 1.42(2) . ?
C20 C18 1.384(17) . ?
C20 C19 1.580(14) . ?
C20 C21 1.706(16) . ?
C16 F3 1.467(17) 8_565 ?
C16 F3 1.467(17) . ?
C19 F5 1.104(11) . ?
C19 F6 1.232(11) . ?
C19 F7 1.401(16) . ?
C19 C21 1.815(15) . ?
C18 H18 0.9300 . ?

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
O4 Mn1 O2 162.42(19) . . ?
O4 Mn1 O3 83.90(14) . 8_565 ?
O2 Mn1 O3 83.25(14) . 8_565 ?
O4 Mn1 O3 83.90(14) . . ?
O2 Mn1 O3 83.25(14) . . ?
O3 Mn1 O3 85.86(18) 8_565 . ?
O4 Mn1 N3 99.53(13) . 8_565 ?
O2 Mn1 N3 92.78(13) . 8_565 ?
O3 Mn1 N3 175.53(13) 8_565 8_565 ?
O3 Mn1 N3 91.62(13) . 8_565 ?
O4 Mn1 N3 99.53(13) . . ?
O2 Mn1 N3 92.78(13) . . ?
O3 Mn1 N3 91.63(13) 8_565 . ?
O3 Mn1 N3 175.53(13) . . ?
N3 Mn1 N3 90.64(18) 8_565 . ?
C15 N3 C14 117.6(4) . . ?
C15 N3 Mn1 119.2(3) . . ?
C14 N3 Mn1 123.2(3) . . ?
C17 O2 Mn1 123.8(6) . . ?
C23 O4 Mn1 125.6(5) . . ?
O1 N1 C5 115.9(4) . . ?
O1 N1 C1 116.0(4) . . ?
C5 N1 C1 124.9(4) . . ?
C10 N2 C3 117.3(4) . . ?
N1 C5 C4 109.5(4) . . ?
N1 C5 C8 108.6(4) . . ?
C4 C5 C8 108.8(4) . . ?
N1 C5 C9 108.8(4) . . ?
C4 C5 C9 111.7(4) . . ?
C8 C5 C9 109.4(4) . . ?
C13 C12 C11 119.5(4) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
N3 C14 C13 123.1(4) . . ?
N3 C14 H14 118.5 . . ?
C13 C14 H14 118.5 . . ?
C15 C11 C12 117.5(4) . . ?
C15 C11 C10 119.3(4) . . ?
C12 C11 C10 123.1(4) . . ?
C3 C2 C1 114.2(4) . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C21 O3 C20 86.5(7) . . ?
C21 O3 Mn1 124.4(5) . . ?
C20 O3 Mn1 124.3(5) . . ?
N1 C1 C6 107.4(4) . . ?
N1 C1 C2 109.9(4) . . ?
C6 C1 C2 109.6(4) . . ?
N1 C1 C7 109.5(4) . . ?
C6 C1 C7 109.5(4) . . ?
C2 C1 C7 110.9(4) . . ?
N2 C3 C4 107.9(4) . . ?
N2 C3 C2 109.7(4) . . ?
C4 C3 C2 108.2(4) . . ?
N2 C3 H3 110.3 . . ?
C4 C3 H3 110.3 . . ?
C2 C3 H3 110.3 . . ?
N2 C10 C11 122.0(5) . . ?
N2 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C3 C4 C5 114.1(4) . . ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
N3 C15 C11 123.5(4) . . ?
N3 C15 H15 118.2 . . ?
C11 C15 H15 118.2 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C12 C13 C14 118.8(5) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C21 C22 C23 124.5(9) . . ?
C21 C22 H22 117.8 . . ?
C23 C22 H22 117.7 . . ?
F9 C24 F10 103.5(10) . 8_565 ?
F9 C24 F10 103.5(10) . . ?
F10 C24 F10 105(2) 8_565 . ?
F9 C24 C23 128.0(14) . . ?
F10 C24 C23 107.3(9) 8_565 . ?
F10 C24 C23 107.3(9) . . ?
O2 C17 C18 130.8(10) . . ?
O2 C17 C16 114.8(13) . . ?
C18 C17 C16 114.4(13) . . ?
O4 C23 C24 125.0(9) . . ?
O4 C23 C22 117.6(6) . . ?
C24 C23 C22 103.7(7) . . ?
O4 C23 C22 117.6(6) . 8_565 ?
C24 C23 C22 103.7(7) . 8_565 ?
C22 C23 C22 79.6(9) . 8_565 ?
O3 C20 C18 127.7(10) . . ?
O3 C20 C19 109.2(10) . . ?
C18 C20 C19 123.0(10) . . ?
O3 C20 C21 46.3(5) . . ?
C18 C20 C21 159.6(9) . . ?
C19 C20 C21 66.9(8) . . ?
F1 C16 F2 106(2) . . ?
F1 C16 C17 129(2) . . ?
F2 C16 C17 122(2) . . ?
F1 C16 F3 103.3(14) . 8_565 ?
F2 C16 F3 58.5(11) . 8_565 ?
C17 C16 F3 89.4(11) . 8_565 ?
F1 C16 F3 103.3(14) . . ?
F2 C16 F3 58.5(11) . . ?
C17 C16 F3 115.2(16) . . ?
F3 C16 F3 116(2) 8_565 . ?
F5 C19 F6 130.5(11) . . ?
F5 C19 F7 88.3(12) . . ?
F6 C19 F7 88.9(11) . . ?
F5 C19 C20 112.7(11) . . ?
F6 C19 C20 105.5(9) . . ?
F7 C19 C20 131.9(12) . . ?
F5 C19 C21 118.3(13) . . ?
F6 C19 C21 107.5(9) . . ?
F7 C19 C21 72.0(10) . . ?
C20 C19 C21 59.8(6) . . ?
C17 C18 C20 122.4(10) . . ?
C17 C18 H18 118.8 . . ?
C20 C18 H18 118.8 . . ?
O3 C21 C22 127.4(9) . . ?
O3 C21 C20 47.2(5) . . ?
C22 C21 C20 155.5(9) . . ?
O3 C21 C19 97.0(8) . . ?
C22 C21 C19 134.3(9) . . ?
C20 C21 C19 53.2(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C5 C4 -167.6(4) . . . . ?
C1 N1 C5 C4 33.9(6) . . . . ?
O1 N1 C5 C8 -48.9(6) . . . . ?
C1 N1 C5 C8 152.6(5) . . . . ?
O1 N1 C5 C9 70.1(5) . . . . ?
C1 N1 C5 C9 -88.5(5) . . . . ?
C15 N3 C14 C13 -0.6(7) . . . . ?
Mn1 N3 C14 C13 179.1(4) . . . . ?
C13 C12 C11 C15 0.4(7) . . . . ?
C13 C12 C11 C10 179.6(4) . . . . ?
O1 N1 C1 C6 49.1(6) . . . . ?
C5 N1 C1 C6 -152.3(5) . . . . ?
O1 N1 C1 C2 168.2(4) . . . . ?
C5 N1 C1 C2 -33.3(6) . . . . ?
O1 N1 C1 C7 -69.8(5) . . . . ?
C5 N1 C1 C7 88.8(5) . . . . ?
C3 C2 C1 N1 44.7(6) . . . . ?
C3 C2 C1 C6 162.5(4) . . . . ?
C3 C2 C1 C7 -76.5(5) . . . . ?
C10 N2 C3 C4 121.3(5) . . . . ?
C10 N2 C3 C2 -121.0(5) . . . . ?
C1 C2 C3 N2 -177.0(4) . . . . ?
C1 C2 C3 C4 -59.6(5) . . . . ?
C3 N2 C10 C11 -178.7(4) . . . . ?
C15 C11 C10 N2 -173.9(4) . . . . ?
C12 C11 C10 N2 6.8(7) . . . . ?
N2 C3 C4 C5 179.0(4) . . . . ?
C2 C3 C4 C5 60.4(5) . . . . ?
N1 C5 C4 C3 -46.1(6) . . . . ?
C8 C5 C4 C3 -164.7(4) . . . . ?
C9 C5 C4 C3 74.5(5) . . . . ?
C14 N3 C15 C11 0.6(6) . . . . ?
Mn1 N3 C15 C11 -179.1(3) . . . . ?
C12 C11 C15 N3 -0.5(7) . . . . ?
C10 C11 C15 N3 -179.8(4) . . . . ?
C11 C12 C13 C14 -0.4(7) . . . . ?
N3 C14 C13 C12 0.5(7) . . . . ?
Mn1 O2 C17 C18 12.5(13) . . . . ?
Mn1 O2 C17 C16 -165.8(7) . . . . ?
Mn1 O4 C23 C24 180.000(1) . . . . ?
Mn1 O4 C23 C22 -46.2(7) . . . . ?
Mn1 O4 C23 C22 46.2(7) . . . 8_565 ?
F9 C24 C23 O4 180.000(1) . . . . ?
F10 C24 C23 O4 -56.4(11) 8_565 . . . ?
F10 C24 C23 O4 56.4(11) . . . . ?
F9 C24 C23 C22 41.2(5) . . . . ?
F10 C24 C23 C22 164.8(12) 8_565 . . . ?
F10 C24 C23 C22 -82.4(13) . . . . ?
F9 C24 C23 C22 -41.2(5) . . . 8_565 ?
F10 C24 C23 C22 82.4(13) 8_565 . . 8_565 ?
F10 C24 C23 C22 -164.8(12) . . . 8_565 ?
C21 C22 C23 O4 22.6(13) . . . . ?
C21 C22 C23 C24 165.1(10) . . . . ?
C21 C22 C23 C22 -93.2(10) . . . 8_565 ?
C21 O3 C20 C18 -154.1(12) . . . . ?
Mn1 O3 C20 C18 -24.1(14) . . . . ?
C21 O3 C20 C19 25.0(9) . . . . ?
Mn1 O3 C20 C19 155.0(6) . . . . ?
Mn1 O3 C20 C21 130.1(7) . . . . ?
O2 C17 C16 F1 165.6(8) . . . . ?
C18 C17 C16 F1 -13.0(15) . . . . ?
O2 C17 C16 F2 -36.3(11) . . . . ?
C18 C17 C16 F2 145.0(10) . . . . ?
O2 C17 C16 F3 -87.7(12) . . . 8_565 ?
C18 C17 C16 F3 93.6(15) . . . 8_565 ?
O2 C17 C16 F3 31(2) . . . . ?
C18 C17 C16 F3 -147.7(16) . . . . ?
O3 C20 C19 F5 -130.0(16) . . . . ?
C18 C20 C19 F5 49(2) . . . . ?
C21 C20 C19 F5 -110.6(17) . . . . ?
O3 C20 C19 F6 82.2(13) . . . . ?
C18 C20 C19 F6 -98.7(13) . . . . ?
C21 C20 C19 F6 101.5(11) . . . . ?
O3 C20 C19 F7 -20.6(18) . . . . ?
C18 C20 C19 F7 158.5(14) . . . . ?
C21 C20 C19 F7 -1.2(14) . . . . ?
O3 C20 C19 C21 -19.4(7) . . . . ?
C18 C20 C19 C21 159.8(11) . . . . ?
O2 C17 C18 C20 5.8(18) . . . . ?
C16 C17 C18 C20 -175.8(11) . . . . ?
O3 C20 C18 C17 1.0(18) . . . . ?
C19 C20 C18 C17 -178.0(10) . . . . ?
C21 C20 C18 C17 -64(3) . . . . ?
C20 O3 C21 C22 148.5(11) . . . . ?
Mn1 O3 C21 C22 18.5(13) . . . . ?
Mn1 O3 C21 C20 -129.9(6) . . . . ?
C20 O3 C21 C19 -20.5(7) . . . . ?
Mn1 O3 C21 C19 -150.4(5) . . . . ?
C23 C22 C21 O3 -8.8(17) . . . . ?
C23 C22 C21 C20 59(2) . . . . ?
C23 C22 C21 C19 155.8(9) . . . . ?
C18 C20 C21 O3 82(3) . . . . ?
C19 C20 C21 O3 -154.3(9) . . . . ?
O3 C20 C21 C22 -88(2) . . . . ?
C18 C20 C21 C22 -6(4) . . . . ?
C19 C20 C21 C22 118(2) . . . . ?
O3 C20 C21 C19 154.3(9) . . . . ?
C18 C20 C21 C19 -124(3) . . . . ?
F5 C19 C21 O3 119.8(13) . . . . ?
F6 C19 C21 O3 -79.4(10) . . . . ?
F7 C19 C21 O3 -162.3(10) . . . . ?
C20 C19 C21 O3 18.7(6) . . . . ?
F5 C19 C21 C22 -47.9(19) . . . . ?
F6 C19 C21 C22 112.9(13) . . . . ?
F7 C19 C21 C22 30.0(14) . . . . ?
C20 C19 C21 C22 -149.0(13) . . . . ?
F5 C19 C21 C20 101.2(14) . . . . ?
F6 C19 C21 C20 -98.1(11) . . . . ?
F7 C19 C21 C20 179.0(11) . . . . ?

_refine_diff_density_max         1.029
_refine_diff_density_min         -1.183
_refine_diff_density_rms         0.093

####################################################################### 
# 
# 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_5
_audit_block_doi                 10.5517/ccdc.csd.cc1yxpl4
_database_code_depnum_ccdc_archive 'CCDC 1815037'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/c8ce00061a 2018
_audit_update_record             
;
2018-04-03 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H23 Cu0.50 F6 N3 O3'
_chemical_formula_weight         499.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pnma

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

_cell_length_a                   16.3979(7)
_cell_length_b                   25.7808(11)
_cell_length_c                   10.7851(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4559.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6520
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      26.38

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2052
_exptl_absorpt_coefficient_mu    0.579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8930
_exptl_absorpt_correction_T_max  0.9182
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            50672
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4103
_reflns_number_gt                3468
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1683P)²+23.2197P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4103
_refine_ls_number_parameters     335
_refine_ls_number_restraints     70
_refine_ls_R_factor_all          0.1091
_refine_ls_R_factor_gt           0.0965
_refine_ls_wR_factor_ref         0.2823
_refine_ls_wR_factor_gt          0.2659
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.67705(6) 0.7500 0.51570(9) 0.0281(4) Uani 1 2 d S . .
O3 O 0.7488(3) 0.80445(17) 0.5912(4) 0.0391(10) Uani 1 1 d . . .
O4 O 0.6148(4) 0.7500 0.7041(6) 0.0470(16) Uani 1 2 d S . 1
N3 N 0.6080(3) 0.69382(18) 0.4364(4) 0.0295(10) Uani 1 1 d . . .
O1 O 0.6537(4) 0.4701(2) -0.3391(4) 0.0566(14) Uani 1 1 d . . .
N1 N 0.6385(3) 0.4935(2) -0.2359(5) 0.0375(12) Uani 1 1 d . . .
N2 N 0.5919(3) 0.5738(2) 0.0980(5) 0.0400(12) Uani 1 1 d . . .
C15 C 0.6330(4) 0.6715(2) 0.3307(5) 0.0344(13) Uani 1 1 d . . .
H15 H 0.6817 0.6829 0.2959 0.041 Uiso 1 1 calc R . .
C11 C 0.5910(4) 0.6327(2) 0.2704(6) 0.0339(13) Uani 1 1 d . . .
C5 C 0.5920(4) 0.5429(2) -0.2468(6) 0.0376(14) Uani 1 1 d . . .
C14 C 0.5384(4) 0.6768(3) 0.4864(6) 0.0362(13) Uani 1 1 d . . .
H14 H 0.5202 0.6916 0.5600 0.043 Uiso 1 1 calc R . .
C12 C 0.5185(4) 0.6158(2) 0.3249(6) 0.0388(14) Uani 1 1 d . . .
H12 H 0.4881 0.5895 0.2881 0.047 Uiso 1 1 calc R . .
C10 C 0.6234(4) 0.6118(2) 0.1536(6) 0.0390(14) Uani 1 1 d . . .
H10 H 0.6693 0.6273 0.1192 0.047 Uiso 1 1 calc R . .
C4 C 0.5633(4) 0.5600(3) -0.1177(6) 0.0407(14) Uani 1 1 d . . .
H4A H 0.5433 0.5954 -0.1231 0.049 Uiso 1 1 calc R . .
H4B H 0.5180 0.5382 -0.0927 0.049 Uiso 1 1 calc R . .
C3 C 0.6282(4) 0.5577(3) -0.0188(6) 0.0379(14) Uani 1 1 d . . .
H3 H 0.6742 0.5802 -0.0405 0.046 Uiso 1 1 calc R . .
C1 C 0.6919(4) 0.4792(3) -0.1289(6) 0.0389(14) Uani 1 1 d . . .
C8 C 0.6456(5) 0.5840(3) -0.3075(7) 0.0560(19) Uani 1 1 d . . .
H8A H 0.6920 0.5908 -0.2556 0.084 Uiso 1 1 calc R . .
H8B H 0.6148 0.6153 -0.3182 0.084 Uiso 1 1 calc R . .
H8C H 0.6639 0.5718 -0.3868 0.084 Uiso 1 1 calc R . .
C13 C 0.4926(4) 0.6381(3) 0.4328(6) 0.0419(15) Uani 1 1 d . . .
H13 H 0.4443 0.6272 0.4697 0.050 Uiso 1 1 calc R . .
C6 C 0.7780(4) 0.4984(3) -0.1508(6) 0.0515(18) Uani 1 1 d . . .
H6A H 0.7974 0.4857 -0.2291 0.077 Uiso 1 1 calc R . .
H6B H 0.8130 0.4861 -0.0857 0.077 Uiso 1 1 calc R . .
H6C H 0.7783 0.5357 -0.1516 0.077 Uiso 1 1 calc R . .
C9 C 0.5174(5) 0.5329(3) -0.3280(7) 0.0548(19) Uani 1 1 d . . .
H9A H 0.5348 0.5223 -0.4092 0.082 Uiso 1 1 calc R . .
H9B H 0.4858 0.5642 -0.3345 0.082 Uiso 1 1 calc R . .
H9C H 0.4848 0.5061 -0.2915 0.082 Uiso 1 1 calc R . .
C2 C 0.6560(4) 0.5013(3) -0.0087(6) 0.0407(15) Uani 1 1 d . . .
H2A H 0.6098 0.4801 0.0158 0.049 Uiso 1 1 calc R . .
H2B H 0.6968 0.4987 0.0562 0.049 Uiso 1 1 calc R . .
C7 C 0.6921(5) 0.4200(3) -0.1209(7) 0.0554(19) Uani 1 1 d . . .
H7A H 0.6376 0.4078 -0.1061 0.083 Uiso 1 1 calc R . .
H7B H 0.7269 0.4092 -0.0541 0.083 Uiso 1 1 calc R . .
H7C H 0.7119 0.4058 -0.1974 0.083 Uiso 1 1 calc R . .
C23 C 0.6565(8) 0.7500 0.7983(10) 0.082(5) Uani 1 2 d S . 1
C21 C 0.7702(7) 0.8077(5) 0.6991(12) 0.038(3) Uani 0.50 1 d P . 1
C22 C 0.7294(8) 0.7883(6) 0.8044(12) 0.045(3) Uani 0.50 1 d P . 1
H17 H 0.7473 0.7991 0.8821 0.054 Uiso 0.50 1 calc PR . 1
C19 C 0.8253(8) 0.8075(5) 0.5859(13) 0.042(3) Uani 0.50 1 d P . -1
O2 O 0.7715(4) 0.7500 0.3634(6) 0.0451(16) Uani 1 2 d S . .
C16 C 0.8427(7) 0.7500 0.3905(12) 0.093(6) Uani 1 2 d SD . .
C18 C 0.8737(8) 0.7875(5) 0.4936(13) 0.047(3) Uani 0.50 1 d PD . .
H16 H 0.9284 0.7969 0.4925 0.056 Uiso 0.50 1 calc PR . .
F1 F 0.8575(5) 0.8844(3) 0.6734(8) 0.116(2) Uani 1 1 d U . .
F4 F 0.9788(7) 0.7500 0.3045(10) 0.118(3) Uani 1 2 d SU . .
F6 F 0.8854(8) 0.7500 0.1828(13) 0.144(4) Uani 1 2 d SU . .
F7 F 0.6688(8) 0.7500 1.0128(12) 0.141(4) Uani 1 2 d SU . .
C20 C 0.8606(7) 0.8364(4) 0.6993(11) 0.082(2) Uani 1 1 d U . .
C24 C 0.6241(11) 0.7500 0.9181(17) 0.093(4) Uani 1 2 d SU . .
C17 C 0.9059(8) 0.7500 0.2985(15) 0.086(5) Uani 1 2 d S . .
F3 F 0.9272(6) 0.8173(4) 0.7240(10) 0.156(3) Uani 1 1 d U . .
F8 F 0.5727(7) 0.7109(4) 0.9327(11) 0.172(4) Uani 1 1 d U . .
F2 F 0.8393(8) 0.8397(5) 0.8121(11) 0.185(4) Uani 1 1 d U . .
F5 F 0.9073(14) 0.6920(9) 0.294(2) 0.171(8) Uani 0.50 1 d PU . .


_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
Cu1 O3 2.004(4) 8_575 ?
Cu1 O3 2.004(4) . ?
Cu1 N3 2.027(5) 8_575 ?
Cu1 N3 2.027(5) . ?
Cu1 O2 2.258(6) . ?
Cu1 O4 2.274(7) . ?
O3 C21 1.218(14) . ?
O3 C19 1.259(13) . ?
O4 C23 1.224(13) . ?
N3 C14 1.338(8) . ?
N3 C15 1.341(8) . ?
O1 N1 1.290(7) . ?
N1 C5 1.488(8) . ?
N1 C1 1.495(8) . ?
N2 C10 1.257(8) . ?
N2 C3 1.455(8) . ?
C15 C11 1.379(9) . ?
C15 H15 0.9300 . ?
C11 C12 1.395(9) . ?
C11 C10 1.469(9) . ?
C5 C8 1.524(10) . ?
C5 C9 1.526(9) . ?
C5 C4 1.535(9) . ?
C14 C13 1.375(9) . ?
C14 H14 0.9300 . ?
C12 C13 1.366(9) . ?
C12 H12 0.9300 . ?
C10 H10 0.9300 . ?
C4 C3 1.508(9) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 C2 1.528(9) . ?
C3 H3 0.9800 . ?
C1 C6 1.515(10) . ?
C1 C7 1.529(10) . ?
C1 C2 1.533(9) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C13 H13 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C23 C24 1.40(2) . ?
C23 C22 1.553(16) 8_575 ?
C23 C22 1.553(16) . ?
C21 C22 1.410(19) . ?
C21 C19 1.518(19) . ?
C21 C20 1.656(16) . ?
C22 C22 1.98(3) 8_575 ?
C22 H17 0.9300 . ?
C19 C18 1.37(2) . ?
C19 C20 1.544(17) . ?
O2 C16 1.202(13) . ?
C16 C17 1.435(17) . ?
C16 C18 1.559(14) . ?
C16 C18 1.559(14) 8_575 ?
C18 C18 1.93(3) 8_575 ?
C18 H16 0.9300 . ?
F1 C20 1.270(12) . ?
F4 C17 1.196(16) . ?
F6 C17 1.293(19) . ?
F7 C24 1.26(2) . ?
C20 F3 1.226(13) . ?
C20 F2 1.269(15) . ?
C24 F8 1.323(14) . ?
C24 F8 1.323(14) 8_575 ?
C17 F5 1.50(2) 8_575 ?
C17 F5 1.50(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
O3 Cu1 O3 88.9(3) 8_575 . ?
O3 Cu1 N3 177.97(19) 8_575 8_575 ?
O3 Cu1 N3 89.92(18) . 8_575 ?
O3 Cu1 N3 89.92(18) 8_575 . ?
O3 Cu1 N3 177.97(19) . . ?
N3 Cu1 N3 91.2(3) 8_575 . ?
O3 Cu1 O2 83.87(18) 8_575 . ?
O3 Cu1 O2 83.87(18) . . ?
N3 Cu1 O2 94.35(18) 8_575 . ?
N3 Cu1 O2 94.34(18) . . ?
O3 Cu1 O4 84.27(17) 8_575 . ?
O3 Cu1 O4 84.27(17) . . ?
N3 Cu1 O4 97.28(18) 8_575 . ?
N3 Cu1 O4 97.28(18) . . ?
O2 Cu1 O4 163.4(2) . . ?
C21 O3 C19 75.6(9) . . ?
C21 O3 Cu1 127.3(7) . . ?
C19 O3 Cu1 127.6(7) . . ?
C23 O4 Cu1 119.4(7) . . ?
C14 N3 C15 117.6(5) . . ?
C14 N3 Cu1 122.7(4) . . ?
C15 N3 Cu1 119.7(4) . . ?
O1 N1 C5 115.5(5) . . ?
O1 N1 C1 116.0(5) . . ?
C5 N1 C1 124.9(5) . . ?
C10 N2 C3 117.9(6) . . ?
N3 C15 C11 124.0(6) . . ?
N3 C15 H15 118.0 . . ?
C11 C15 H15 118.0 . . ?
C15 C11 C12 117.0(6) . . ?
C15 C11 C10 119.4(6) . . ?
C12 C11 C10 123.7(6) . . ?
N1 C5 C8 109.5(6) . . ?
N1 C5 C9 108.2(5) . . ?
C8 C5 C9 109.5(6) . . ?
N1 C5 C4 109.4(5) . . ?
C8 C5 C4 111.5(6) . . ?
C9 C5 C4 108.8(6) . . ?
N3 C14 C13 122.2(6) . . ?
N3 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
C13 C12 C11 119.5(6) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
N2 C10 C11 123.1(6) . . ?
N2 C10 H10 118.5 . . ?
C11 C10 H10 118.5 . . ?
C3 C4 C5 114.4(5) . . ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
N2 C3 C4 108.2(5) . . ?
N2 C3 C2 109.5(5) . . ?
C4 C3 C2 107.5(5) . . ?
N2 C3 H3 110.5 . . ?
C4 C3 H3 110.5 . . ?
C2 C3 H3 110.5 . . ?
N1 C1 C6 110.1(5) . . ?
N1 C1 C7 106.9(6) . . ?
C6 C1 C7 109.5(6) . . ?
N1 C1 C2 109.7(5) . . ?
C6 C1 C2 111.6(6) . . ?
C7 C1 C2 108.9(6) . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C12 C13 C14 119.6(6) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 C2 C1 114.0(5) . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C23 C24 123.7(13) . . ?
O4 C23 C22 117.7(8) . 8_575 ?
C24 C23 C22 104.7(10) . 8_575 ?
O4 C23 C22 117.7(8) . . ?
C24 C23 C22 104.7(10) . . ?
C22 C23 C22 79.0(12) 8_575 . ?
O3 C21 C22 127.4(11) . . ?
O3 C21 C19 53.4(8) . . ?
C22 C21 C19 158.2(12) . . ?
O3 C21 C20 106.9(10) . . ?
C22 C21 C20 125.6(11) . . ?
C19 C21 C20 58.0(8) . . ?
C21 C22 C23 123.8(11) . . ?
C21 C22 C22 110.8(8) . 8_575 ?
C23 C22 C22 50.5(6) . 8_575 ?
C21 C22 H17 118.1 . . ?
C23 C22 H17 118.1 . . ?
C22 C22 H17 107.4 8_575 . ?
O3 C19 C18 125.8(12) . . ?
O3 C19 C21 51.0(7) . . ?
C18 C19 C21 158.0(12) . . ?
O3 C19 C20 111.6(11) . . ?
C18 C19 C20 122.6(11) . . ?
C21 C19 C20 65.5(9) . . ?
C16 O2 Cu1 119.3(8) . . ?
O2 C16 C17 122.2(12) . . ?
O2 C16 C18 119.3(9) . . ?
C17 C16 C18 104.9(10) . . ?
O2 C16 C18 119.3(9) . 8_575 ?
C17 C16 C18 104.9(10) . 8_575 ?
C18 C16 C18 76.6(12) . 8_575 ?
C19 C18 C16 124.2(12) . . ?
C19 C18 C18 112.1(8) . 8_575 ?
C16 C18 C18 51.7(6) . 8_575 ?
C19 C18 H16 117.9 . . ?
C16 C18 H16 117.9 . . ?
C18 C18 H16 105.1 8_575 . ?
F3 C20 F2 93.7(11) . . ?
F3 C20 F1 118.3(11) . . ?
F2 C20 F1 97.7(11) . . ?
F3 C20 C19 108.3(11) . . ?
F2 C20 C19 133.5(12) . . ?
F1 C20 C19 106.3(9) . . ?
F3 C20 C21 128.2(11) . . ?
F2 C20 C21 77.6(10) . . ?
F1 C20 C21 113.5(9) . . ?
C19 C20 C21 56.5(7) . . ?
F7 C24 F8 105.9(12) . . ?
F7 C24 F8 105.9(12) . 8_575 ?
F8 C24 F8 99.2(16) . 8_575 ?
F7 C24 C23 122.0(16) . . ?
F8 C24 C23 110.6(12) . . ?
F8 C24 C23 110.6(12) 8_575 . ?
F4 C17 F6 108.2(13) . . ?
F4 C17 C16 133.2(16) . . ?
F6 C17 C16 118.6(13) . . ?
F4 C17 F5 89.2(11) . 8_575 ?
F6 C17 F5 88.4(12) . 8_575 ?
C16 C17 F5 91.9(10) . 8_575 ?
F4 C17 F5 89.2(11) . . ?
F6 C17 F5 88.4(12) . . ?
C16 C17 F5 91.9(10) . . ?
F5 C17 F5 176(2) 8_575 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 Cu1 O3 C21 -51.2(9) 8_575 . . . ?
N3 Cu1 O3 C21 130.4(8) 8_575 . . . ?
N3 Cu1 O3 C21 -106(5) . . . . ?
O2 Cu1 O3 C21 -135.2(8) . . . . ?
O4 Cu1 O3 C21 33.1(8) . . . . ?
O3 Cu1 O3 C19 49.8(9) 8_575 . . . ?
N3 Cu1 O3 C19 -128.5(9) 8_575 . . . ?
N3 Cu1 O3 C19 -5(6) . . . . ?
O2 Cu1 O3 C19 -34.1(9) . . . . ?
O4 Cu1 O3 C19 134.2(9) . . . . ?
O3 Cu1 O4 C23 44.74(13) 8_575 . . . ?
O3 Cu1 O4 C23 -44.74(13) . . . . ?
N3 Cu1 O4 C23 -133.93(13) 8_575 . . . ?
N3 Cu1 O4 C23 133.93(13) . . . . ?
O2 Cu1 O4 C23 0.000(3) . . . . ?
O3 Cu1 N3 C14 97.4(5) 8_575 . . . ?
O3 Cu1 N3 C14 153(5) . . . . ?
N3 Cu1 N3 C14 -84.3(5) 8_575 . . . ?
O2 Cu1 N3 C14 -178.8(5) . . . . ?
O4 Cu1 N3 C14 13.2(5) . . . . ?
O3 Cu1 N3 C15 -81.2(4) 8_575 . . . ?
O3 Cu1 N3 C15 -26(5) . . . . ?
N3 Cu1 N3 C15 97.1(4) 8_575 . . . ?
O2 Cu1 N3 C15 2.7(4) . . . . ?
O4 Cu1 N3 C15 -165.4(4) . . . . ?
C14 N3 C15 C11 0.6(9) . . . . ?
Cu1 N3 C15 C11 179.3(5) . . . . ?
N3 C15 C11 C12 -0.6(9) . . . . ?
N3 C15 C11 C10 178.8(5) . . . . ?
O1 N1 C5 C8 -69.4(7) . . . . ?
C1 N1 C5 C8 88.1(7) . . . . ?
O1 N1 C5 C9 49.9(8) . . . . ?
C1 N1 C5 C9 -152.7(6) . . . . ?
O1 N1 C5 C4 168.2(6) . . . . ?
C1 N1 C5 C4 -34.3(8) . . . . ?
C15 N3 C14 C13 -0.4(9) . . . . ?
Cu1 N3 C14 C13 -179.0(5) . . . . ?
C15 C11 C12 C13 0.4(9) . . . . ?
C10 C11 C12 C13 -179.0(6) . . . . ?
C3 N2 C10 C11 178.3(6) . . . . ?
C15 C11 C10 N2 174.6(6) . . . . ?
C12 C11 C10 N2 -6.0(10) . . . . ?
N1 C5 C4 C3 46.7(7) . . . . ?
C8 C5 C4 C3 -74.5(7) . . . . ?
C9 C5 C4 C3 164.7(6) . . . . ?
C10 N2 C3 C4 -122.3(6) . . . . ?
C10 N2 C3 C2 120.8(6) . . . . ?
C5 C4 C3 N2 -178.8(5) . . . . ?
C5 C4 C3 C2 -60.7(7) . . . . ?
O1 N1 C1 C6 68.3(7) . . . . ?
C5 N1 C1 C6 -89.1(7) . . . . ?
O1 N1 C1 C7 -50.6(8) . . . . ?
C5 N1 C1 C7 152.0(6) . . . . ?
O1 N1 C1 C2 -168.5(6) . . . . ?
C5 N1 C1 C2 34.1(8) . . . . ?
C11 C12 C13 C14 -0.2(10) . . . . ?
N3 C14 C13 C12 0.2(10) . . . . ?
N2 C3 C2 C1 177.4(5) . . . . ?
C4 C3 C2 C1 60.1(7) . . . . ?
N1 C1 C2 C3 -45.5(8) . . . . ?
C6 C1 C2 C3 76.8(7) . . . . ?
C7 C1 C2 C3 -162.2(6) . . . . ?
Cu1 O4 C23 C24 180.000(4) . . . . ?
Cu1 O4 C23 C22 -45.9(9) . . . 8_575 ?
Cu1 O4 C23 C22 45.9(9) . . . . ?
C19 O3 C21 C22 -152.7(15) . . . . ?
Cu1 O3 C21 C22 -26.0(17) . . . . ?
Cu1 O3 C21 C19 126.6(8) . . . . ?
C19 O3 C21 C20 23.8(9) . . . . ?
Cu1 O3 C21 C20 150.4(6) . . . . ?
O3 C21 C22 C23 12(2) . . . . ?
C19 C21 C22 C23 -72(4) . . . . ?
C20 C21 C22 C23 -164.0(10) . . . . ?
O3 C21 C22 C22 67.5(13) . . . 8_575 ?
C19 C21 C22 C22 -16(3) . . . 8_575 ?
C20 C21 C22 C22 -108.4(11) . . . 8_575 ?
O4 C23 C22 C21 -25.6(17) . . . . ?
C24 C23 C22 C21 -167.5(12) . . . . ?
C22 C23 C22 C21 90.1(13) 8_575 . . . ?
O4 C23 C22 C22 -115.7(11) . . . 8_575 ?
C24 C23 C22 C22 102.5(9) . . . 8_575 ?
C21 O3 C19 C18 152.5(15) . . . . ?
Cu1 O3 C19 C18 26.3(18) . . . . ?
Cu1 O3 C19 C21 -126.3(9) . . . . ?
C21 O3 C19 C20 -26.5(10) . . . . ?
Cu1 O3 C19 C20 -152.8(7) . . . . ?
C22 C21 C19 O3 101(3) . . . . ?
C20 C21 C19 O3 -152.9(10) . . . . ?
O3 C21 C19 C18 -90(3) . . . . ?
C22 C21 C19 C18 10(6) . . . . ?
C20 C21 C19 C18 117(3) . . . . ?
O3 C21 C19 C20 152.9(10) . . . . ?
C22 C21 C19 C20 -107(3) . . . . ?
O3 Cu1 O2 C16 -44.78(13) 8_575 . . . ?
O3 Cu1 O2 C16 44.78(13) . . . . ?
N3 Cu1 O2 C16 134.24(13) 8_575 . . . ?
N3 Cu1 O2 C16 -134.23(13) . . . . ?
O4 Cu1 O2 C16 0.000(1) . . . . ?
Cu1 O2 C16 C17 180.0 . . . . ?
Cu1 O2 C16 C18 -45.3(9) . . . . ?
Cu1 O2 C16 C18 45.3(9) . . . 8_575 ?
O3 C19 C18 C16 -10(2) . . . . ?
C21 C19 C18 C16 63(4) . . . . ?
C20 C19 C18 C16 168.7(11) . . . . ?
O3 C19 C18 C18 -67.9(14) . . . 8_575 ?
C21 C19 C18 C18 5(4) . . . 8_575 ?
C20 C19 C18 C18 111.0(10) . . . 8_575 ?
O2 C16 C18 C19 23.9(17) . . . . ?
C17 C16 C18 C19 165.4(12) . . . . ?
C18 C16 C18 C19 -92.4(13) 8_575 . . . ?
O2 C16 C18 C18 116.4(11) . . . 8_575 ?
C17 C16 C18 C18 -102.2(9) . . . 8_575 ?
O3 C19 C20 F3 146.6(11) . . . . ?
C18 C19 C20 F3 -32.4(18) . . . . ?
C21 C19 C20 F3 124.2(12) . . . . ?
O3 C19 C20 F2 32.6(19) . . . . ?
C18 C19 C20 F2 -146.4(16) . . . . ?
C21 C19 C20 F2 10.2(15) . . . . ?
O3 C19 C20 F1 -85.4(13) . . . . ?
C18 C19 C20 F1 95.6(14) . . . . ?
C21 C19 C20 F1 -107.8(11) . . . . ?
O3 C19 C20 C21 22.4(9) . . . . ?
C18 C19 C20 C21 -156.7(15) . . . . ?
O3 C21 C20 F3 -110.0(14) . . . . ?
C22 C21 C20 F3 66.5(19) . . . . ?
C19 C21 C20 F3 -87.6(15) . . . . ?
O3 C21 C20 F2 165.1(11) . . . . ?
C22 C21 C20 F2 -18.4(15) . . . . ?
C19 C21 C20 F2 -172.4(12) . . . . ?
O3 C21 C20 F1 72.0(13) . . . . ?
C22 C21 C20 F1 -111.4(14) . . . . ?
C19 C21 C20 F1 94.5(11) . . . . ?
O3 C21 C20 C19 -22.5(9) . . . . ?
C22 C21 C20 C19 154.1(15) . . . . ?
O4 C23 C24 F7 180.000(3) . . . . ?
C22 C23 C24 F7 41.1(7) 8_575 . . . ?
C22 C23 C24 F7 -41.1(7) . . . . ?
O4 C23 C24 F8 54.5(11) . . . . ?
C22 C23 C24 F8 -84.4(14) 8_575 . . . ?
C22 C23 C24 F8 -166.6(11) . . . . ?
O4 C23 C24 F8 -54.5(11) . . . 8_575 ?
C22 C23 C24 F8 166.6(11) 8_575 . . 8_575 ?
C22 C23 C24 F8 84.4(14) . . . 8_575 ?
O2 C16 C17 F4 180.0 . . . . ?
C18 C16 C17 F4 39.9(7) . . . . ?
C18 C16 C17 F4 -39.9(7) 8_575 . . . ?
O2 C16 C17 F6 0.000(1) . . . . ?
C18 C16 C17 F6 -140.1(7) . . . . ?
C18 C16 C17 F6 140.1(7) 8_575 . . . ?
O2 C16 C17 F5 89.3(12) . . . 8_575 ?
C18 C16 C17 F5 -50.8(14) . . . 8_575 ?
C18 C16 C17 F5 -130.6(13) 8_575 . . 8_575 ?
O2 C16 C17 F5 -89.3(12) . . . . ?
C18 C16 C17 F5 130.6(13) . . . . ?
C18 C16 C17 F5 50.8(14) 8_575 . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.490
_refine_diff_density_min         -1.431
_refine_diff_density_rms         0.128


####################################################################### 
# 
# 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_7
_audit_block_doi                 10.5517/ccdc.csd.cc1yv4yw
_database_code_depnum_ccdc_archive 'CCDC 1812599'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/c8ce00061a 2018
_audit_update_record             
;
2018-04-03 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H24 Cu F12 N3 O5'
_chemical_formula_weight         738.01

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'
Cu Cu 0.3201 1.2651 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.5751(4)
_cell_length_b                   32.4090(13)
_cell_length_c                   10.9213(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.8646(13)
_cell_angle_gamma                90
_cell_volume                     3243.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9889
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      25.96

_exptl_crystal_description       sheet
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.780
_shelx_estimated_absorpt_T_min   0.735
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scans
_exptl_absorpt_correction_T_min  0.7354
_exptl_absorpt_correction_T_max  0.9695
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34518
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.794
_diffrn_reflns_theta_max         28.288
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8008
_reflns_number_gt                5730
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0606P)²+2.4127P] 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         8008
_refine_ls_number_parameters     446
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1416
_refine_ls_wR_factor_gt          0.1293
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
Cu1 Cu 0.76779(3) 0.09080(2) 0.62675(3) 0.04009(11) Uani 1 1 d . . . . .
O2 O 0.90968(19) 0.11207(6) 0.78334(17) 0.0460(4) Uani 1 1 d . . . . .
N3 N 0.6226(2) 0.06843(7) 0.4707(2) 0.0403(5) Uani 1 1 d . . . . .
N2 N 0.6622(2) 0.14462(6) 0.5559(2) 0.0384(5) Uani 1 1 d . . . . .
O4 O 0.8613(2) 0.03629(6) 0.6679(2) 0.0549(5) Uani 1 1 d . . . . .
C3 C 0.6921(3) 0.18691(8) 0.6057(3) 0.0444(6) Uani 1 1 d . . . . .
H3 H 0.628748 0.206294 0.545778 0.053 Uiso 1 1 calc R U . . .
C10 C 0.5601(3) 0.13874(8) 0.4531(3) 0.0446(6) Uani 1 1 d . . . . .
H10 H 0.503731 0.160730 0.411263 0.053 Uiso 1 1 calc R U . . .
O3 O 0.6210(2) 0.08063(7) 0.75896(19) 0.0536(5) Uani 1 1 d . . . . .
O5 O 0.9440(2) 0.10456(7) 0.5310(2) 0.0598(5) Uani 1 1 d . . . . .
C11 C 0.5327(3) 0.09712(8) 0.4017(3) 0.0433(6) Uani 1 1 d . . . . .
C4 C 0.6627(3) 0.18975(9) 0.7337(3) 0.0513(7) Uani 1 1 d . . . . .
H4A H 0.721398 0.169209 0.790377 0.062 Uiso 1 1 calc R U . . .
H4B H 0.560947 0.183078 0.722453 0.062 Uiso 1 1 calc R U . . .
C5 C 0.6949(4) 0.23184(10) 0.7973(3) 0.0619(8) Uani 1 1 d . . . . .
C22 C 0.9133(3) 0.10798(9) 0.8987(3) 0.0482(7) Uani 1 1 d . . . . .
C23 C 0.8051(4) 0.09637(10) 0.9506(3) 0.0559(7) Uani 1 1 d . . . . .
H23 H 0.825172 0.095995 1.039123 0.067 Uiso 1 1 calc R U . . .
C1 C 0.8950(4) 0.24029(9) 0.6761(3) 0.0564(8) Uani 1 1 d . . . . .
C19 C 1.0628(4) 0.08730(11) 0.5724(3) 0.0622(8) Uani 1 1 d . . . . .
C2 C 0.8501(3) 0.19738(9) 0.6205(3) 0.0485(6) Uani 1 1 d . . . . .
H2A H 0.867319 0.195557 0.537440 0.058 Uiso 1 1 calc R U . . .
H2B H 0.911642 0.177012 0.675812 0.058 Uiso 1 1 calc R U . . .
C12 C 0.4230(4) 0.08713(11) 0.2920(3) 0.0608(8) Uani 1 1 d . . . . .
H12 H 0.361307 0.107408 0.245509 0.073 Uiso 1 1 calc R U . . .
C15 C 0.6062(4) 0.02941(9) 0.4315(3) 0.0551(7) Uani 1 1 d . . . . .
H15 H 0.669132 0.009531 0.478844 0.066 Uiso 1 1 calc R U . . .
C18 C 1.0950(4) 0.05115(12) 0.6447(4) 0.0692(9) Uani 1 1 d . . . . .
H18 H 1.190605 0.041544 0.667774 0.083 Uiso 1 1 calc R U . . .
N1 N 0.8382(3) 0.24680(8) 0.7879(3) 0.0624(7) Uani 1 1 d . . . . .
C13 C 0.4069(4) 0.04649(12) 0.2531(3) 0.0686(9) Uani 1 1 d . . . . .
H13 H 0.333848 0.038985 0.179776 0.082 Uiso 1 1 calc R U . . .
C24 C 0.6658(3) 0.08508(9) 0.8756(3) 0.0531(7) Uani 1 1 d . . . . .
C14 C 0.4991(4) 0.01740(11) 0.3229(3) 0.0650(9) Uani 1 1 d . . . . .
H14 H 0.489853 -0.010122 0.297803 0.078 Uiso 1 1 calc R U . . .
C21 C 1.0613(5) 0.12017(14) 0.9887(4) 0.0808(12) Uani 1 1 d . . . . .
C6 C 1.0605(4) 0.24187(12) 0.7249(4) 0.0762(10) Uani 1 1 d . . . . .
H6A H 1.090894 0.269091 0.756058 0.114 Uiso 1 1 calc R U . . .
H6B H 1.100809 0.235233 0.656402 0.114 Uiso 1 1 calc R U . . .
H6C H 1.094401 0.222277 0.792966 0.114 Uiso 1 1 calc R U . . .
F8 F 1.1014(5) 0.15471(14) 0.9612(4) 0.228(3) Uani 1 1 d . . . . .
C16 C 1.0454(6) -0.01004(15) 0.7614(6) 0.0976(15) Uani 1 1 d . . . . .
O1 O 0.8947(4) 0.27702(9) 0.8616(3) 0.1039(10) Uani 1 1 d . . . . .
C25 C 0.5520(6) 0.0776(2) 0.9457(5) 0.0968(14) Uani 1 1 d . . . . .
F9 F 1.0676(3) 0.12128(13) 1.1092(2) 0.1472(14) Uani 1 1 d . . . . .
F4 F 1.3029(3) 0.08673(15) 0.5520(4) 0.180(2) Uani 1 1 d . . . . .
F5 F 1.1556(4) 0.12581(13) 0.4318(4) 0.1625(17) Uani 1 1 d . . . . .
F3 F 1.1555(8) -0.02834(18) 0.7400(8) 0.168(3) Uani 0.8 1 d . . P . .
F6 F 1.2366(6) 0.13881(18) 0.6248(6) 0.234(3) Uani 1 1 d . . . . .
F13 F 0.5974(5) 0.0803(2) 1.0665(4) 0.166(2) Uani 0.85 1 d . . P . .
C7 C 0.8391(5) 0.27418(11) 0.5768(4) 0.0828(12) Uani 1 1 d . . . . .
H7A H 0.734926 0.272105 0.543084 0.124 Uiso 1 1 calc R U . . .
H7B H 0.882786 0.271057 0.508552 0.124 Uiso 1 1 calc R U . . .
H7C H 0.864361 0.300673 0.616300 0.124 Uiso 1 1 calc R U . . .
C9 C 0.5761(5) 0.26332(13) 0.7366(5) 0.1006(15) Uani 1 1 d . . . . .
H9A H 0.606659 0.290231 0.770669 0.151 Uiso 1 1 calc R U . . .
H9B H 0.487434 0.255917 0.755489 0.151 Uiso 1 1 calc R U . . .
H9C H 0.559452 0.263582 0.645605 0.151 Uiso 1 1 calc R U . . .
F7 F 1.1602(3) 0.09387(16) 0.9846(4) 0.1786(19) Uani 1 1 d . . . . .
C8 C 0.7100(5) 0.22696(15) 0.9391(4) 0.0956(14) Uani 1 1 d . . . . .
H8A H 0.791568 0.209386 0.977647 0.143 Uiso 1 1 calc R U . . .
H8B H 0.622509 0.214894 0.949378 0.143 Uiso 1 1 calc R U . . .
H8C H 0.725331 0.253530 0.979646 0.143 Uiso 1 1 calc R U . . .
C20 C 1.1888(5) 0.1097(2) 0.5433(6) 0.1047(16) Uani 1 1 d . . . . .
F2 F 0.9558(6) -0.04155(11) 0.7102(5) 0.1631(17) Uani 0.9 1 d . . P . .
F11 F 0.4782(7) 0.1126(2) 0.9441(8) 0.226(3) Uani 0.85 1 d . . P . .
F15 F 0.4356(5) 0.0608(2) 0.8835(5) 0.159(2) Uani 0.8 1 d . . P . .
C27 C 0.9944(4) 0.02925(10) 0.6832(3) 0.0597(8) Uani 1 1 d . . . . .
F16 F 0.5640(11) 0.0368(3) 0.9817(10) 0.172(3) Uani 0.5 1 d . . P . .
F17 F 1.1867(15) -0.0064(5) 0.831(3) 0.164(8) Uani 0.3 1 d . . P . .
F1 F 1.075(2) -0.0041(5) 0.8769(11) 0.163(7) Uani 0.5 1 d . . P . .
F19 F 0.9904(14) -0.0137(6) 0.8560(16) 0.154(7) Uani 0.5 1 d . . 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
Cu1 O4 1.9726(19) . ?
Cu1 O2 1.9742(18) . ?
Cu1 N3 1.997(2) . ?
Cu1 N2 2.052(2) . ?
Cu1 O5 2.272(2) . ?
Cu1 O3 2.312(2) . ?
O2 C22 1.257(3) . ?
N3 C15 1.330(4) . ?
N3 C11 1.340(3) . ?
N2 C10 1.271(3) . ?
N2 C3 1.472(3) . ?
O4 C27 1.257(4) . ?
C3 C4 1.507(4) . ?
C3 C2 1.513(4) . ?
C10 C11 1.455(4) . ?
O3 C24 1.229(4) . ?
O5 C19 1.230(4) . ?
C11 C12 1.383(4) . ?
C4 C5 1.521(4) . ?
C5 N1 1.487(4) . ?
C5 C8 1.521(5) . ?
C5 C9 1.529(5) . ?
C22 C23 1.370(4) . ?
C22 C21 1.524(4) . ?
C23 C24 1.396(4) . ?
C1 N1 1.490(4) . ?
C1 C6 1.519(5) . ?
C1 C7 1.527(4) . ?
C1 C2 1.528(4) . ?
C19 C18 1.397(5) . ?
C19 C20 1.518(6) . ?
C12 C13 1.379(5) . ?
C15 C14 1.380(4) . ?
C18 C27 1.357(5) . ?
N1 O1 1.283(3) . ?
C13 C14 1.363(5) . ?
C24 C25 1.521(5) . ?
C21 F8 1.248(5) . ?
C21 F7 1.284(6) . ?
C21 F9 1.300(5) . ?
C16 F1 1.225(13) . ?
C16 F3 1.289(7) . ?
C16 F19 1.294(15) . ?
C16 F2 1.347(7) . ?
C16 F17 1.351(14) . ?
C16 C27 1.532(5) . ?
C25 F15 1.250(6) . ?
C25 F13 1.267(6) . ?
C25 F11 1.331(8) . ?
C25 F16 1.377(9) . ?
F4 C20 1.301(6) . ?
F5 C20 1.278(6) . ?
F6 C20 1.288(7) . ?
F2 F19 1.78(2) . ?
F1 F19 0.83(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
O4 Cu1 O2 87.85(8) . . ?
O4 Cu1 N3 91.55(9) . . ?
O2 Cu1 N3 178.75(8) . . ?
O4 Cu1 N2 171.40(9) . . ?
O2 Cu1 N2 99.77(8) . . ?
N3 Cu1 N2 80.91(8) . . ?
O4 Cu1 O5 86.11(8) . . ?
O2 Cu1 O5 85.06(8) . . ?
N3 Cu1 O5 95.99(9) . . ?
N2 Cu1 O5 90.55(8) . . ?
O4 Cu1 O3 92.76(8) . . ?
O2 Cu1 O3 84.20(7) . . ?
N3 Cu1 O3 94.74(8) . . ?
N2 Cu1 O3 91.98(8) . . ?
O5 Cu1 O3 169.24(8) . . ?
C22 O2 Cu1 130.04(18) . . ?
C15 N3 C11 118.8(2) . . ?
C15 N3 Cu1 127.5(2) . . ?
C11 N3 Cu1 113.73(17) . . ?
C10 N2 C3 118.9(2) . . ?
C10 N2 Cu1 111.97(18) . . ?
C3 N2 Cu1 129.11(16) . . ?
C27 O4 Cu1 124.6(2) . . ?
N2 C3 C4 109.3(2) . . ?
N2 C3 C2 109.2(2) . . ?
C4 C3 C2 109.7(2) . . ?
N2 C10 C11 119.1(2) . . ?
C24 O3 Cu1 122.56(19) . . ?
C19 O5 Cu1 118.2(2) . . ?
N3 C11 C12 121.8(3) . . ?
N3 C11 C10 114.3(2) . . ?
C12 C11 C10 123.9(3) . . ?
C3 C4 C5 114.2(3) . . ?
N1 C5 C4 109.3(2) . . ?
N1 C5 C8 106.7(3) . . ?
C4 C5 C8 108.6(3) . . ?
N1 C5 C9 109.8(3) . . ?
C4 C5 C9 112.0(3) . . ?
C8 C5 C9 110.4(3) . . ?
O2 C22 C23 129.7(3) . . ?
O2 C22 C21 111.7(3) . . ?
C23 C22 C21 118.5(3) . . ?
C22 C23 C24 122.5(3) . . ?
N1 C1 C6 107.4(3) . . ?
N1 C1 C7 110.1(3) . . ?
C6 C1 C7 109.9(3) . . ?
N1 C1 C2 109.1(2) . . ?
C6 C1 C2 108.3(3) . . ?
C7 C1 C2 111.9(3) . . ?
O5 C19 C18 128.2(3) . . ?
O5 C19 C20 114.4(3) . . ?
C18 C19 C20 117.4(3) . . ?
C3 C2 C1 113.8(2) . . ?
C13 C12 C11 118.6(3) . . ?
N3 C15 C14 122.3(3) . . ?
C27 C18 C19 123.6(3) . . ?
O1 N1 C5 115.8(3) . . ?
O1 N1 C1 115.8(3) . . ?
C5 N1 C1 125.0(2) . . ?
C14 C13 C12 119.5(3) . . ?
O3 C24 C23 128.7(3) . . ?
O3 C24 C25 114.7(3) . . ?
C23 C24 C25 116.6(3) . . ?
C13 C14 C15 119.0(3) . . ?
F8 C21 F7 107.8(5) . . ?
F8 C21 F9 107.0(4) . . ?
F7 C21 F9 103.6(4) . . ?
F8 C21 C22 111.7(3) . . ?
F7 C21 C22 111.2(4) . . ?
F9 C21 C22 114.9(4) . . ?
F1 C16 F3 107.6(9) . . ?
F1 C16 F19 38.6(12) . . ?
F3 C16 F19 130.3(7) . . ?
F1 C16 F2 118.3(11) . . ?
F3 C16 F2 91.8(6) . . ?
F19 C16 F2 84.5(9) . . ?
F1 C16 F17 60.9(12) . . ?
F3 C16 F17 53.3(10) . . ?
F19 C16 F17 97.6(14) . . ?
F2 C16 F17 135.5(8) . . ?
F1 C16 C27 112.6(8) . . ?
F3 C16 C27 115.3(5) . . ?
F19 C16 C27 112.5(8) . . ?
F2 C16 C27 109.8(4) . . ?
F17 C16 C27 110.2(7) . . ?
F15 C25 F13 125.3(5) . . ?
F15 C25 F11 88.8(6) . . ?
F13 C25 F11 88.6(5) . . ?
F15 C25 F16 73.8(6) . . ?
F13 C25 F16 78.1(6) . . ?
F11 C25 F16 145.2(5) . . ?
F15 C25 C24 116.8(4) . . ?
F13 C25 C24 115.7(4) . . ?
F11 C25 C24 108.3(5) . . ?
F16 C25 C24 106.5(5) . . ?
F5 C20 F6 107.4(6) . . ?
F5 C20 F4 106.0(5) . . ?
F6 C20 F4 104.3(5) . . ?
F5 C20 C19 113.7(4) . . ?
F6 C20 C19 110.5(4) . . ?
F4 C20 C19 114.4(5) . . ?
C16 F2 F19 46.5(5) . . ?
O4 C27 C18 130.3(3) . . ?
O4 C27 C16 111.8(3) . . ?
C18 C27 C16 117.9(3) . . ?
F19 F1 C16 75(2) . . ?
F1 F19 C16 66.3(15) . . ?
F1 F19 F2 110(2) . . ?
C16 F19 F2 49.0(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N2 C3 C4 116.3(3) . . . . ?
Cu1 N2 C3 C4 -65.6(3) . . . . ?
C10 N2 C3 C2 -123.7(3) . . . . ?
Cu1 N2 C3 C2 54.5(3) . . . . ?
C3 N2 C10 C11 178.4(2) . . . . ?
Cu1 N2 C10 C11 0.0(3) . . . . ?
C15 N3 C11 C12 0.6(4) . . . . ?
Cu1 N3 C11 C12 -178.5(2) . . . . ?
C15 N3 C11 C10 -180.0(3) . . . . ?
Cu1 N3 C11 C10 0.9(3) . . . . ?
N2 C10 C11 N3 -0.6(4) . . . . ?
N2 C10 C11 C12 178.8(3) . . . . ?
N2 C3 C4 C5 178.0(2) . . . . ?
C2 C3 C4 C5 58.2(3) . . . . ?
C3 C4 C5 N1 -45.4(4) . . . . ?
C3 C4 C5 C8 -161.4(3) . . . . ?
C3 C4 C5 C9 76.4(4) . . . . ?
Cu1 O2 C22 C23 -17.5(5) . . . . ?
Cu1 O2 C22 C21 165.6(2) . . . . ?
O2 C22 C23 C24 2.7(5) . . . . ?
C21 C22 C23 C24 179.4(3) . . . . ?
Cu1 O5 C19 C18 21.2(5) . . . . ?
Cu1 O5 C19 C20 -156.5(3) . . . . ?
N2 C3 C2 C1 -178.1(2) . . . . ?
C4 C3 C2 C1 -58.2(3) . . . . ?
N1 C1 C2 C3 45.6(3) . . . . ?
C6 C1 C2 C3 162.3(3) . . . . ?
C7 C1 C2 C3 -76.4(4) . . . . ?
N3 C11 C12 C13 -0.3(5) . . . . ?
C10 C11 C12 C13 -179.6(3) . . . . ?
C11 N3 C15 C14 -0.6(4) . . . . ?
Cu1 N3 C15 C14 178.4(2) . . . . ?
O5 C19 C18 C27 -1.2(6) . . . . ?
C20 C19 C18 C27 176.5(4) . . . . ?
C4 C5 N1 O1 -164.7(3) . . . . ?
C8 C5 N1 O1 -47.5(4) . . . . ?
C9 C5 N1 O1 72.1(4) . . . . ?
C4 C5 N1 C1 37.0(4) . . . . ?
C8 C5 N1 C1 154.2(3) . . . . ?
C9 C5 N1 C1 -86.1(4) . . . . ?
C6 C1 N1 O1 47.3(4) . . . . ?
C7 C1 N1 O1 -72.4(4) . . . . ?
C2 C1 N1 O1 164.5(3) . . . . ?
C6 C1 N1 C5 -154.4(3) . . . . ?
C7 C1 N1 C5 85.9(4) . . . . ?
C2 C1 N1 C5 -37.2(4) . . . . ?
C11 C12 C13 C14 -0.2(5) . . . . ?
Cu1 O3 C24 C23 -0.1(5) . . . . ?
Cu1 O3 C24 C25 179.1(3) . . . . ?
C22 C23 C24 O3 5.9(5) . . . . ?
C22 C23 C24 C25 -173.3(4) . . . . ?
C12 C13 C14 C15 0.2(5) . . . . ?
N3 C15 C14 C13 0.2(5) . . . . ?
O2 C22 C21 F8 50.3(6) . . . . ?
C23 C22 C21 F8 -127.0(5) . . . . ?
O2 C22 C21 F7 -70.3(4) . . . . ?
C23 C22 C21 F7 112.5(4) . . . . ?
O2 C22 C21 F9 172.4(4) . . . . ?
C23 C22 C21 F9 -4.9(6) . . . . ?
O3 C24 C25 F15 12.7(8) . . . . ?
C23 C24 C25 F15 -168.0(6) . . . . ?
O3 C24 C25 F13 177.1(6) . . . . ?
C23 C24 C25 F13 -3.7(8) . . . . ?
O3 C24 C25 F11 -85.4(6) . . . . ?
C23 C24 C25 F11 93.9(6) . . . . ?
O3 C24 C25 F16 92.6(7) . . . . ?
C23 C24 C25 F16 -88.1(7) . . . . ?
O5 C19 C20 F5 -38.8(7) . . . . ?
C18 C19 C20 F5 143.2(5) . . . . ?
O5 C19 C20 F6 82.0(6) . . . . ?
C18 C19 C20 F6 -96.0(6) . . . . ?
O5 C19 C20 F4 -160.7(5) . . . . ?
C18 C19 C20 F4 21.2(7) . . . . ?
F1 C16 F2 F19 19.2(12) . . . . ?
F3 C16 F2 F19 130.3(7) . . . . ?
F17 C16 F2 F19 95.3(19) . . . . ?
C27 C16 F2 F19 -112.0(8) . . . . ?
Cu1 O4 C27 C18 -19.8(5) . . . . ?
Cu1 O4 C27 C16 158.4(3) . . . . ?
C19 C18 C27 O4 -2.3(6) . . . . ?
C19 C18 C27 C16 179.5(4) . . . . ?
F1 C16 C27 O4 -82.5(12) . . . . ?
F3 C16 C27 O4 153.6(6) . . . . ?
F19 C16 C27 O4 -40.6(11) . . . . ?
F2 C16 C27 O4 51.6(6) . . . . ?
F17 C16 C27 O4 -148.4(15) . . . . ?
F1 C16 C27 C18 96.0(12) . . . . ?
F3 C16 C27 C18 -28.0(8) . . . . ?
F19 C16 C27 C18 137.9(10) . . . . ?
F2 C16 C27 C18 -129.9(5) . . . . ?
F17 C16 C27 C18 30.0(16) . . . . ?
F3 C16 F1 F19 -133.7(19) . . . . ?
F2 C16 F1 F19 -32(2) . . . . ?
F17 C16 F1 F19 -160(3) . . . . ?
C27 C16 F1 F19 98(2) . . . . ?
C16 F1 F19 F2 21.9(14) . . . . ?
F3 C16 F19 F1 65(3) . . . . ?
F2 C16 F19 F1 152(2) . . . . ?
F17 C16 F19 F1 17(2) . . . . ?
C27 C16 F19 F1 -98.5(19) . . . . ?
F1 C16 F19 F2 -152(2) . . . . ?
F3 C16 F19 F2 -87.8(11) . . . . ?
F17 C16 F19 F2 -135.2(8) . . . . ?
C27 C16 F19 F2 109.1(7) . . . . ?
C16 F2 F19 F1 -26.9(19) . . . . ?

_refine_diff_density_max         0.566
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.055

