# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_cu_pb029_3
_database_code_depnum_ccdc_archive 'CCDC 2000087'
loop_
_audit_author_name
_audit_author_address
'Stephen Loeb'
;University of Windsor
Canada
;
_audit_update_record             
;
2020-04-29 deposited with the CCDC.	2020-05-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_cu_pb029_3          
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The crystals were weakly diffracting resulting in a low
resolution data collection.
;
_vrf_PLAT084_cu_pb029_3          
;
PROBLEM: High wR2 Value (i.e. > 0.25) ................... 0.52 Report
RESPONSE: The poor quality data and disorder present in the structure
result in a high wR1 value.
;
_vrf_PLAT316_cu_pb029_3          
;
PROBLEM: Too many H on C in C=N Moiety in Main Residue .. C12 Check
RESPONSE: the C12 carbon is actually an sp3 carbon however with the low 
precision bonds the shorter than expected C-N bond result in it appearing
as a C=N bond.
;
_vrf_PLAT411_cu_pb029_3          
;
PROBLEM: Short Inter H...H Contact H33A ..H33A . 1.64 Ang.
RESPONSE: The hydrogen atoms are placed in calculated positions
which for C33, on the crown ether which features residual 
disorder, results in them being orientated closer than expected.
;
_vrf_PLAT082_cu_pb029_3          
;
PROBLEM: High R1 Value .................................. 0.19 Report
RESPONSE: The poor quality data and disorder present in the structure
result in a high R1 value.
;
_vrf_PLAT088_cu_pb029_3          
;
PROBLEM: Poor Data / Parameter Ratio .................... 7.60 Note
RESPONSE: The weakly diffracting crystals and disorder of some parts 
of the molecule and anions resulted in poor data that required a large 
number of restraints to model the rotaxane and anions in a chgemically 
sensible manner.
;
_vrf_PLAT241_cu_pb029_3          
;
PROBLEM: High MainMol Ueq as Compared to Neighbors of C20 Check
RESPONSE: The poor data resulted in large thermal parameters for the
atoms of the rotaxane. The ester moiety containing C20 may posses some
unresolved disorder that is unable to be modeled with the quality of 
the data. 
;
_vrf_PLAT242_cu_pb029_3          
;
PROBLEM: Low MainMol Ueq as Compared to Neighbors of O2 Check
RESPONSE: The poor data resulted in large thermal parameters for the
atoms of the rotaxane. The ester moiety containing O2 may posses some
unresolved disorder that is unable to be modeled with the quality of 
the data. 
;
_vrf_PLAT260_cu_pb029_3          
;
PROBLEM: Large Average Ueq of Residue Including F5 0.517 Check
RESPONSE:  The large thermal parameters of the fluorine atoms of the 
tetrafluoroborate anion containg F5 is due to the disorder of the anion
and the poor data. The disorder of the anion was attempted to be resolved
by modeling the fluorine atoms over two positions.
;
_vrf_PLAT340_cu_pb029_3          
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.02522 Ang.
RESPONSE: The poor quality of the data and the residual disorder in the
rotaxane and anions results in a low precision for the C-C bonds.
;
_vrf_PLAT410_cu_pb029_3          
;
PROBLEM: Short Intra H...H Contact H46A ..H48B . 1.87 Ang.
RESPONSE: The hydrogen atoms are placed in calculated positions
which for C46 and C48, on the crown ether which features residual 
disorder, results in them being orientated closer than expected.
;
# end Validation Reply Form
_audit_creation_date             2020-04-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
loeb@uwindsor.ca
bwilson@uwindsor.ca
martinep@uwindsor.ca
_chemical_name_common            ?
_chemical_name_systematic        '[5]rotaxane'
_chemical_formula_moiety         'C96 H96 N8 O16, 3(B2 F8), 4(C24 H32 O8)'
_chemical_formula_sum            'C192 H224 B6 F24 N8 O48'
_chemical_formula_weight         3932.64
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C50 H40 N2 O10 B F4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           86
_space_group_name_H-M_alt        'P 42/n'
_space_group_name_Hall           '-P 4bc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y, x+1/2, z+1/2'
'y+1/2, -x, z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y, -x-1/2, -z-1/2'
'-y-1/2, x, -z-1/2'

_cell_length_a                   25.0521(11)
_cell_length_b                   25.0521(11)
_cell_length_c                   15.1716(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     9521.8(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7197
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.8500
_cell_measurement_theta_min      2.4510
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.724
_exptl_absorpt_coefficient_mu    0.957
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic green'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             4124
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.074
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            38551
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        50.412
_diffrn_reflns_theta_max         50.412
_diffrn_reflns_theta_min         2.494
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    193.23 288.23   1.00   75.00    --  -88.38 -59.86 110.31   95
  2  ω   -134.58 -25.58   1.00   75.00    -- -103.38  84.78  59.60  109
  3  ω    -11.09  81.91   1.00   75.00    --    4.61  59.85 -20.31   93
  4  φ     13.54 250.54   1.00   75.00 -86.12-103.38 -59.16    --   237
  5  φ     71.67 299.67   1.00   75.00 -23.88-103.38  30.17    --   228
  6  φ     91.67 240.67   1.00   75.00  -3.05   5.65  30.17    --   149
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0430431000
_diffrn_orient_matrix_UB_12      -0.0423501000
_diffrn_orient_matrix_UB_13      0.0192231000
_diffrn_orient_matrix_UB_21      0.0434462000
_diffrn_orient_matrix_UB_22      -0.0433310000
_diffrn_orient_matrix_UB_23      0.0048268000
_diffrn_orient_matrix_UB_31      0.0061988000
_diffrn_orient_matrix_UB_32      0.0102779000
_diffrn_orient_matrix_UB_33      0.0996931000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'I\mS Microfocus Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2121
_reflns_number_total             4886
_reflns_odcompleteness_completeness 99.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.573
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.677
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     656
_refine_ls_number_reflns         4886
_refine_ls_number_restraints     611
_refine_ls_R_factor_all          0.2752
_refine_ls_R_factor_gt           0.1892
_refine_ls_restrained_S_all      1.654
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4626
_refine_ls_wR_factor_ref         0.5216
_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. Hydrogen atoms were included
in calculated positions with isotropic displacement parameters 1.2 times
the isotropic equivalent of their carrier atoms. The low resolution data 
resulted the thermal parameters being chemically unrealistic therefore the
RIGU restraint was applied to the rotaxane axel, macrocycle and tetrafluoroborate 
anions. The disorder of the ester, macrocycle and tetrafluoroborate anions
required the DFIX restraint in order for the bond lengths and angles to be 
modeled in a chemically sensible manner. The ISOR and SIMU restraints were 
required by some  atoms in order for the thermal parameters of the atoms to 
be modeled in a chemically sensible manner. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups,
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F4-B1
 1.402 with sigma of 0.02
 F1-B1
 1.402 with sigma of 0.02
 F2-B1
 1.402 with sigma of 0.02
 F3-B1
 1.402 with sigma of 0.02
 B2-F5
 1.402 with sigma of 0.02
 F6A-B2
 1.402 with sigma of 0.02
 B2-F8A
 1.402 with sigma of 0.02
 B2-F6B
 1.402 with sigma of 0.02
 B2-F7B
 1.402 with sigma of 0.02
 F8B-B2
 1.402 with sigma of 0.02
 F7A-B2
 1.402 with sigma of 0.02
 F7A-F8A
 2.21 with sigma of 0.02
 F8A-F6A
 2.21 with sigma of 0.02
 F6A-F7A
 2.21 with sigma of 0.02
 F5-F7A
 2.21 with sigma of 0.02
 F8A-F5
 2.21 with sigma of 0.02
 F6A-F5
 2.21 with sigma of 0.02
 F8B-F7B
 2.21 with sigma of 0.02
 F7B-F6B
 2.21 with sigma of 0.02
 F6B-F8B
 2.21 with sigma of 0.02
 F8B-F5
 2.21 with sigma of 0.02
 F6B-F5
 2.21 with sigma of 0.02
 F7B-F5
 2.21 with sigma of 0.02
 C24A-C23
 1.4 with sigma of 0.02
 C24B-C23
 1.4 with sigma of 0.02
 C24A-O4
 2.4 with sigma of 0.02
 C24B-O4
 2.4 with sigma of 0.02
 C47-O12
 1.36 with sigma of 0.02
 C47-C48
 1.395 with sigma of 0.02
 O5-C48
 1.5 with sigma of 0.02
 F7B-H27_$1
 -2.2 with sigma of 0.02
 F3-H24A
 -2.2 with sigma of 0.02
 F4-H24F
 -2.2 with sigma of 0.02
 F3-H24C
 -2.2 with sigma of 0.02
 H24B-F3
 -2.2 with sigma of 0.02
 H47A-F8B
 -2.2 with sigma of 0.02
 H47B-F8B
 -2.2 with sigma of 0.01
 H24E-F4
 -2.2 with sigma of 0.02
 C20-C21
 1.4 with sigma of 0.02
 C31-C32
 1.4 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C24A \\sim C23: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
Uanis(F6B) \\sim Ueq: with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(C24A) \\sim Ueq, Uanis(C24B) \\sim Ueq: with sigma of 0.04 and sigma for
terminal atoms of 0.08
Uanis(C21) \\sim Ueq: with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(F6A) \\sim Ueq: with sigma of 0.04 and sigma for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 C44, O10, C43, C42, C37, C41, O9, C38, O11, C40, C36, C39, C45, C35, C46, O8,
 C34, O12, C33, O7, C32, C31, O6, C30, C25, C29, C26, O5, C28, C27, C48, C47
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F2, B1, F4, F3, F1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F6A, F8A, F5, B2, F7A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F8B, B2, F5, F7B, F6B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7, N1, H1, C1, C4, C2, C5, C3, H2, C6, H3, C11, C10, H11, H7, C8, C9, H10,
 H8, C12, N2, H2A, H2B, C13, C18, C14, H18, C17, H14, C15, C16, C22, C19, H16,
 O4, O3, O2, O1, C23, C20, C24B, C24A, C21, H20A, H20B, H21A, H21B, H21C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: F3(0.5) F8A(0.5) F4(0.5) F6B(0.5) F6A(0.5) F7B(0.5) H23C(0.5)
 H23D(0.5) H23A(0.5) H23B(0.5) C24B(0.5) H24A(0.5) H24B(0.5) H24C(0.5) B1(0.5)
 F8B(0.5) F7A(0.5) C24A(0.5) H24D(0.5) H24E(0.5) H24F(0.5)
6.a Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), C32(H32A,H32B), C12(H12A,H12B), C43(H43A,H43B), C33(H33A,H33B),
 C36(H36A,H36B), C34(H34A,H34B), C46(H46A,H46B), C31(H31A,H31B), C48(H48A,H48B),
  C47(H47A,H47B), C23(H23C,H23D), C23(H23A,H23B), C44(H44A,H44B), C35(H35A,
 H35B), C45(H45A,H45B), C20(H20A,H20B)
6.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C26(H26), C27(H27), C28(H28), C29(H29), C10(H10),
 C11(H11), C7(H7), C8(H8), C18(H18), C16(H16), C14(H14), C38(H38), C39(H39),
 C40(H40), C41(H41)
6.c Fitted hexagon refined as free rotating group:
 C30(C25,C26,C27,C28,C29), C42(C37,C38,C39,C40,C41)
6.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C24B(H24A,H24B,H24C), C24A(H24D,H24E,H24F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N1 N 0.2668(3) 0.3324(2) 0.2443(5) 0.094(2) Uani 1 1 d . U . . .
H1 H 0.260330 0.299353 0.227679 0.113 Uiso 1 1 calc R U . . .
F1 F -0.250000 0.750000 -0.1161(8) 0.154(3) Uani 1 2 d DS TU P . .
C1 C 0.3175(4) 0.3533(3) 0.2653(7) 0.105(3) Uani 1 1 d . U . . .
F2 F -0.250000 0.750000 0.0315(8) 0.186(4) Uani 1 2 d DS TU P . .
C4 C 0.2292(3) 0.3718(3) 0.2539(7) 0.102(3) Uani 1 1 d . U . . .
C2 C 0.3074(4) 0.4066(3) 0.2924(9) 0.126(4) Uani 1 1 d . U . . .
H2 H 0.333270 0.430878 0.314377 0.152 Uiso 1 1 calc R U . . .
C5 C 0.1736(3) 0.3651(3) 0.2403(6) 0.091(3) Uani 1 1 d . U . . .
C6 C 0.1419(3) 0.4146(4) 0.2330(7) 0.100(3) Uani 1 1 d . U . . .
C3 C 0.2549(4) 0.4171(4) 0.2820(8) 0.112(4) Uani 1 1 d . U . . .
H3 H 0.238353 0.450586 0.292525 0.135 Uiso 1 1 calc R U . . .
O10 O 0.0031(6) 0.5750(4) 0.4549(10) 0.215(5) Uani 1 1 d . U . . .
C30 C 0.1052(5) 0.7041(5) 0.1404(8) 0.168(5) Uani 1 1 d . U . . .
C25 C 0.1508(5) 0.6972(4) 0.1914(8) 0.194(6) Uani 1 1 d G U . . .
C26 C 0.1769(5) 0.7413(6) 0.2262(8) 0.256(10) Uani 1 1 d G U . . .
H26 H 0.208072 0.736631 0.261065 0.308 Uiso 1 1 calc R . . . .
C27 C 0.1575(6) 0.7924(5) 0.2101(11) 0.311(14) Uani 1 1 d G U . . .
H27 H 0.175354 0.822563 0.233949 0.373 Uiso 1 1 calc DR . . . .
C28 C 0.1119(7) 0.7993(4) 0.1592(11) 0.320(16) Uani 1 1 d G U . . .
H28 H 0.098602 0.834177 0.148169 0.384 Uiso 1 1 calc R . . . .
C29 C 0.0857(5) 0.7551(6) 0.1243(9) 0.258(10) Uani 1 1 d G U . . .
H29 H 0.054567 0.759859 0.089503 0.309 Uiso 1 1 calc R . . . .
O9 O -0.0720(4) 0.5635(5) 0.3517(11) 0.229(5) Uani 1 1 d . U . . .
C9 C 0.0815(5) 0.5071(4) 0.2217(10) 0.130(4) Uani 1 1 d . U . . .
C10 C 0.0693(5) 0.4696(5) 0.2833(12) 0.162(5) Uani 1 1 d . U . . .
H10 H 0.040774 0.475353 0.323388 0.194 Uiso 1 1 calc R U . . .
C11 C 0.0990(4) 0.4229(4) 0.2870(9) 0.134(4) Uani 1 1 d . U . . .
H11 H 0.089262 0.396028 0.328171 0.161 Uiso 1 1 calc R U . . .
C7 C 0.1566(4) 0.4539(4) 0.1718(8) 0.118(4) Uani 1 1 d . U . . .
H7 H 0.186254 0.449123 0.133650 0.142 Uiso 1 1 calc R U . . .
C8 C 0.1255(5) 0.5009(4) 0.1690(9) 0.139(4) Uani 1 1 d . U . . .
H8 H 0.135378 0.528828 0.129898 0.167 Uiso 1 1 calc R U . . .
O11 O 0.1155(5) 0.5642(5) 0.4355(10) 0.232(5) Uani 1 1 d . U . . .
C18 C -0.0053(7) 0.6552(5) 0.2525(12) 0.174(6) Uani 1 1 d . U . . .
H18 H -0.018781 0.629851 0.211583 0.209 Uiso 1 1 calc R U . . .
N2 N 0.0658(7) 0.5950(4) 0.2846(9) 0.210(6) Uani 1 1 d . U . . .
H2A H 0.100710 0.601816 0.272521 0.252 Uiso 1 1 calc R U . . .
H2B H 0.065098 0.577629 0.337231 0.252 Uiso 1 1 calc R U . . .
C16 C -0.0092(10) 0.7416(7) 0.3344(15) 0.219(7) Uani 1 1 d . U . . .
H16 H -0.027033 0.773368 0.351645 0.263 Uiso 1 1 calc R U . . .
C13 C 0.0401(8) 0.6470(6) 0.2991(15) 0.178(6) Uani 1 1 d . U . . .
C19 C 0.0653(15) 0.7690(12) 0.4258(19) 0.259(9) Uani 1 1 d . U . . .
O4 O -0.1029(6) 0.6850(5) 0.1706(14) 0.289(8) Uani 1 1 d D U . . .
O6 O 0.0841(7) 0.6622(7) 0.1029(12) 0.267(7) Uani 1 1 d . U . . .
C17 C -0.0334(9) 0.7086(7) 0.2710(16) 0.218(6) Uani 1 1 d . U . . .
O5 O 0.1645(6) 0.6484(8) 0.229(2) 0.458(19) Uani 1 1 d D U . . .
O2 O 0.1095(12) 0.7583(8) 0.4487(17) 0.321(10) Uani 1 1 d . U . . .
C14 C 0.0613(8) 0.6813(6) 0.3539(11) 0.194(6) Uani 1 1 d . U . . .
H14 H 0.093800 0.671881 0.382176 0.233 Uiso 1 1 calc R U . . .
O8 O -0.0585(5) 0.5198(7) 0.1630(16) 0.283(8) Uani 1 1 d . U . . .
C32 C 0.0379(9) 0.6189(7) -0.0185(16) 0.256(9) Uani 1 1 d D U . . .
H32A H 0.066606 0.592487 -0.028235 0.307 Uiso 1 1 calc R . . . .
H32B H 0.022160 0.629587 -0.075719 0.307 Uiso 1 1 calc R . . . .
C12 C 0.0492(6) 0.5600(5) 0.2241(12) 0.191(7) Uani 1 1 d . U . . .
H12A H 0.051298 0.577100 0.165321 0.229 Uiso 1 1 calc R . . . .
H12B H 0.011266 0.551502 0.235556 0.229 Uiso 1 1 calc R . . . .
C15 C 0.0396(11) 0.7298(6) 0.3728(15) 0.218(6) Uani 1 1 d . U . . .
O1 O 0.0405(9) 0.8079(5) 0.4536(10) 0.311(9) Uani 1 1 d . U . . .
C43 C 0.0408(11) 0.5789(12) 0.5357(19) 0.285(12) Uani 1 1 d . U . . .
H43A H 0.054648 0.615634 0.543640 0.342 Uiso 1 1 calc R . . . .
H43B H 0.022951 0.567149 0.590533 0.342 Uiso 1 1 calc R . . . .
O3 O -0.1068(8) 0.7631(6) 0.2291(17) 0.398(13) Uani 1 1 d . U . . .
O7 O -0.0074(10) 0.5972(10) 0.0506(17) 0.411(15) Uani 1 1 d . U . . .
C33 C -0.0327(10) 0.5592(9) 0.0324(16) 0.267(10) Uani 1 1 d . U . . .
H33A H -0.006949 0.529425 0.026601 0.320 Uiso 1 1 calc R . . . .
H33B H -0.047157 0.565708 -0.027366 0.320 Uiso 1 1 calc R . . . .
F3 F -0.2101(7) 0.6864(6) -0.0603(12) 0.198(7) Uani 0.5 1 d D U . . .
C36 C -0.1177(7) 0.5485(14) 0.290(2) 0.338(13) Uani 1 1 d . U . . .
H36A H -0.130240 0.580103 0.256981 0.405 Uiso 1 1 calc R . . . .
H36B H -0.147999 0.533552 0.323928 0.405 Uiso 1 1 calc R . . . .
C34 C -0.0751(9) 0.5394(11) 0.082(2) 0.304(14) Uani 1 1 d . U . . .
H34A H -0.101490 0.568204 0.091870 0.364 Uiso 1 1 calc R . . . .
H34B H -0.093002 0.510452 0.048950 0.364 Uiso 1 1 calc R . . . .
F8A F 0.337(2) 0.578(2) 0.3267(16) 0.62(4) Uani 0.5 1 d D U . A 1
O12 O 0.1828(8) 0.5622(17) 0.325(2) 0.46(2) Uani 1 1 d D U . . .
C42 C -0.0420(6) 0.6066(6) 0.4617(12) 0.219(6) Uani 1 1 d . U . . .
C37 C -0.0845(8) 0.5971(5) 0.4049(11) 0.287(11) Uani 1 1 d G U . . .
C38 C -0.1290(6) 0.6302(7) 0.4068(12) 0.286(11) Uani 1 1 d G U . . .
H38 H -0.158078 0.623743 0.367987 0.344 Uiso 1 1 calc R . . . .
C39 C -0.1310(6) 0.6728(6) 0.4653(14) 0.41(2) Uani 1 1 d G U . . .
H39 H -0.161421 0.695483 0.466603 0.494 Uiso 1 1 calc R . . . .
C40 C -0.0885(9) 0.6823(5) 0.5221(10) 0.300(13) Uani 1 1 d G U . . .
H40 H -0.089847 0.711470 0.562121 0.360 Uiso 1 1 calc R . . . .
C41 C -0.0440(7) 0.6492(7) 0.5202(9) 0.298(10) Uani 1 1 d G U . . .
H41 H -0.014930 0.655717 0.559023 0.358 Uiso 1 1 calc R . . . .
F4 F -0.1755(7) 0.7736(8) -0.0696(13) 0.231(8) Uani 0.5 1 d D U . . .
F5 F 0.3945(11) 0.5443(14) 0.226(2) 0.62(2) Uani 1 1 d D U . . .
C46 C 0.2007(12) 0.564(2) 0.406(3) 0.39(2) Uani 1 1 d . U . . .
H46A H 0.196951 0.600069 0.433188 0.471 Uiso 1 1 calc R . . . .
H46B H 0.238054 0.551641 0.411856 0.471 Uiso 1 1 calc R . . . .
C31 C 0.0549(9) 0.6613(10) 0.0284(14) 0.253(11) Uani 1 1 d D U . . .
H31A H 0.022134 0.681757 0.042454 0.304 Uiso 1 1 calc R . . . .
H31B H 0.075051 0.683465 -0.014134 0.304 Uiso 1 1 calc R . . . .
F6B F 0.3138(15) 0.5698(14) 0.1763(18) 0.41(2) Uani 0.5 1 d D U . A 2
C48 C 0.2143(11) 0.6395(15) 0.280(3) 0.57(4) Uani 1 1 d D U . . .
H48A H 0.244568 0.660014 0.255091 0.689 Uiso 1 1 calc R . . . .
H48B H 0.209820 0.648512 0.342914 0.689 Uiso 1 1 calc R . . . .
C21 C 0.1868(15) 0.7791(13) 0.503(2) 0.386(17) Uani 1 1 d D U . . .
H21A H 0.206245 0.790672 0.555481 0.579 Uiso 1 1 calc GR U . . .
H21B H 0.204560 0.793170 0.450117 0.579 Uiso 1 1 calc GR U . . .
H21C H 0.186456 0.739967 0.500266 0.579 Uiso 1 1 calc GR U . . .
F6A F 0.3067(16) 0.5332(17) 0.210(4) 0.63(4) Uani 0.5 1 d D U . A 1
C47 C 0.2204(11) 0.5848(15) 0.267(3) 0.43(2) Uani 1 1 d D U . . .
H47A H 0.257073 0.573200 0.282003 0.516 Uiso 1 1 calc DR . . . .
H47B H 0.212734 0.574860 0.205032 0.516 Uiso 1 1 calc DR . . . .
F7B F 0.3479(9) 0.6052(8) 0.3022(16) 0.311(12) Uani 0.5 1 d D U . A 2
C23 C -0.1474(11) 0.7006(9) 0.109(3) 0.385(17) Uani 1 1 d D U . . .
H23C H -0.172162 0.725642 0.138602 0.462 Uiso 0.5 1 calc R . . B 2
H23D H -0.132720 0.718414 0.055979 0.462 Uiso 0.5 1 calc R . . B 2
H23A H -0.146536 0.678166 0.055196 0.462 Uiso 0.5 1 calc R . . C 1
H23B H -0.182474 0.695735 0.138035 0.462 Uiso 0.5 1 calc R . . C 1
C44 C 0.0805(10) 0.5442(13) 0.511(2) 0.292(13) Uani 1 1 d . U . . .
H44A H 0.063962 0.509966 0.493012 0.350 Uiso 1 1 calc R . . . .
H44B H 0.103513 0.536930 0.562602 0.350 Uiso 1 1 calc R . . . .
C35 C -0.0938(11) 0.5047(11) 0.2244(19) 0.275(9) Uani 1 1 d . U . . .
H35A H -0.076734 0.476702 0.260764 0.330 Uiso 1 1 calc R . . . .
H35B H -0.124257 0.487791 0.193589 0.330 Uiso 1 1 calc R . . . .
C45 C 0.1627(9) 0.5264(9) 0.4407(19) 0.256(8) Uani 1 1 d . U . . .
H45A H 0.170852 0.515171 0.501748 0.308 Uiso 1 1 calc R . . . .
H45B H 0.158429 0.494714 0.402270 0.308 Uiso 1 1 calc R . . . .
C24B C -0.175(2) 0.6535(17) 0.084(3) 0.41(3) Uani 0.5 1 d D U . D 2
H24A H -0.170410 0.626474 0.130529 0.621 Uiso 0.5 1 calc DGR . . D 2
H24B H -0.160314 0.639985 0.028791 0.621 Uiso 0.5 1 calc DGR . . D 2
H24C H -0.212922 0.661442 0.077007 0.621 Uiso 0.5 1 calc DGR . . D 2
C20 C 0.1347(17) 0.7980(13) 0.506(3) 0.46(3) Uani 1 1 d D U . . .
H20A H 0.131621 0.834620 0.482242 0.548 Uiso 1 1 calc R U . . .
H20B H 0.120022 0.796982 0.566842 0.548 Uiso 1 1 calc R U . . .
C22 C -0.0847(16) 0.7202(10) 0.219(3) 0.341(16) Uani 1 1 d . U . . .
B1 B -0.2172(9) 0.7403(9) -0.0429(13) 0.159(6) Uani 0.5 1 d D U . E -1
B2 B 0.3466(11) 0.5635(10) 0.2441(14) 0.50(2) Uani 1 1 d D U . . .
F8B F 0.3248(13) 0.5213(9) 0.298(2) 0.53(3) Uani 0.5 1 d D U . A 2
F7A F 0.3445(12) 0.6126(14) 0.192(2) 0.385(19) Uani 0.5 1 d D U . A 1
C24A C -0.140(2) 0.7549(11) 0.087(2) 0.41(3) Uani 0.5 1 d D U . D 1
H24D H -0.122281 0.773302 0.136002 0.613 Uiso 0.5 1 calc GR . . D 1
H24E H -0.174228 0.771606 0.074674 0.613 Uiso 0.5 1 calc DGR . . D 1
H24F H -0.116981 0.757315 0.034253 0.613 Uiso 0.5 1 calc DGR . . D 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
N1 C1 1.411(11) . ?
N1 C4 1.372(10) . ?
F1 B1 1.403(19) . ?
C1 C2 1.419(12) . ?
C1 C5 1.373(12) 7_566 ?
F2 B1 1.418(18) . ?
C4 C5 1.418(12) . ?
C4 C3 1.372(11) . ?
C2 C3 1.349(12) . ?
C5 C6 1.478(12) . ?
C6 C11 1.368(13) . ?
C6 C7 1.402(13) . ?
O10 C43 1.55(3) . ?
O10 C42 1.383(15) . ?
C30 C25 1.3900 . ?
C30 C29 1.3900 . ?
C30 O6 1.305(15) . ?
C25 C26 1.3900 . ?
C25 O5 1.393(19) . ?
C26 C27 1.3900 . ?
C27 C28 1.3900 . ?
C28 C29 1.3900 . ?
O9 C36 1.52(3) . ?
O9 C37 1.208(17) . ?
C9 C10 1.360(17) . ?
C9 C8 1.371(16) . ?
C9 C12 1.553(16) . ?
C10 C11 1.387(14) . ?
C7 C8 1.411(14) . ?
O11 C44 1.53(3) . ?
O11 C45 1.52(2) . ?
C18 C13 1.35(2) . ?
C18 C17 1.54(2) . ?
N2 C13 1.470(19) . ?
N2 C12 1.334(15) . ?
C16 C17 1.41(3) . ?
C16 C15 1.39(3) . ?
C13 C14 1.31(2) . ?
C19 O2 1.19(4) . ?
C19 C15 1.42(4) . ?
C19 O1 1.23(3) . ?
O4 C23 1.51(3) . ?
O4 C22 1.24(4) . ?
O6 C31 1.35(2) . ?
C17 C22 1.54(4) . ?
O5 C48 1.480(18) . ?
O2 C20 1.47(3) . ?
C14 C15 1.36(2) . ?
O8 C34 1.38(3) . ?
O8 C35 1.34(3) . ?
C32 O7 1.64(3) . ?
C32 C31 1.347(16) . ?
C43 C44 1.37(3) . ?
O3 C22 1.22(2) . ?
O7 C33 1.177(19) . ?
C33 C34 1.39(3) . ?
F3 B1 1.387(18) . ?
C36 C35 1.60(4) . ?
F8A B2 1.328(18) . ?
O12 C46 1.32(5) . ?
O12 C47 1.406(19) . ?
C42 C37 1.3900 . ?
C42 C41 1.3900 . ?
C37 C38 1.3900 . ?
C38 C39 1.3900 . ?
C39 C40 1.3900 . ?
C40 C41 1.3900 . ?
F4 B1 1.395(18) . ?
F5 B2 1.324(17) . ?
C46 C45 1.44(4) . ?
F6B B2 1.325(17) . ?
C48 C47 1.39(2) . ?
C21 C20 1.39(2) . ?
F6A B2 1.359(18) . ?
F7B B2 1.368(18) . ?
C23 C24B 1.415(19) . ?
C23 C24A 1.414(19) . ?
B2 F8B 1.441(18) . ?
B2 F7A 1.465(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
C4 N1 C1 109.0(7) . . ?
N1 C1 C2 104.7(8) . . ?
C5 C1 N1 125.8(7) 7_566 . ?
C5 C1 C2 129.5(9) 7_566 . ?
N1 C4 C5 125.0(8) . . ?
C3 C4 N1 107.8(8) . . ?
C3 C4 C5 127.2(8) . . ?
C3 C2 C1 108.9(9) . . ?
C1 C5 C4 126.6(8) 8_656 . ?
C1 C5 C6 117.3(8) 8_656 . ?
C4 C5 C6 116.1(7) . . ?
C11 C6 C5 120.3(9) . . ?
C11 C6 C7 119.7(9) . . ?
C7 C6 C5 119.9(9) . . ?
C2 C3 C4 109.4(8) . . ?
C42 O10 C43 113.8(19) . . ?
C25 C30 C29 120.0 . . ?
O6 C30 C25 118.4(13) . . ?
O6 C30 C29 121.4(13) . . ?
C30 C25 C26 120.0 . . ?
C30 C25 O5 122.8(12) . . ?
C26 C25 O5 115.1(13) . . ?
C27 C26 C25 120.0 . . ?
C26 C27 C28 120.0 . . ?
C29 C28 C27 120.0 . . ?
C28 C29 C30 120.0 . . ?
C37 O9 C36 112.8(18) . . ?
C10 C9 C8 120.1(11) . . ?
C10 C9 C12 117.2(14) . . ?
C8 C9 C12 122.0(14) . . ?
C9 C10 C11 119.4(12) . . ?
C6 C11 C10 121.6(11) . . ?
C6 C7 C8 117.5(11) . . ?
C9 C8 C7 121.4(12) . . ?
C45 O11 C44 101.8(19) . . ?
C13 C18 C17 114.9(19) . . ?
C12 N2 C13 123.3(15) . . ?
C15 C16 C17 122.8(18) . . ?
C18 C13 N2 115.1(18) . . ?
C14 C13 C18 124.9(18) . . ?
C14 C13 N2 120(2) . . ?
O2 C19 C15 115(3) . . ?
O2 C19 O1 123(3) . . ?
O1 C19 C15 121(3) . . ?
C22 O4 C23 117(2) . . ?
C30 O6 C31 127(2) . . ?
C16 C17 C18 116(2) . . ?
C16 C17 C22 126.9(19) . . ?
C22 C17 C18 117(2) . . ?
C25 O5 C48 124(2) . . ?
C19 O2 C20 115(3) . . ?
C13 C14 C15 124(2) . . ?
C35 O8 C34 121(2) . . ?
C31 C32 O7 98.3(19) . . ?
N2 C12 C9 114.5(11) . . ?
C16 C15 C19 119(2) . . ?
C14 C15 C16 117(2) . . ?
C14 C15 C19 124(3) . . ?
C44 C43 O10 101(3) . . ?
C33 O7 C32 120(3) . . ?
O7 C33 C34 125(3) . . ?
O9 C36 C35 105.8(14) . . ?
O8 C34 C33 112(2) . . ?
C46 O12 C47 110(3) . . ?
O10 C42 C37 118.8(17) . . ?
O10 C42 C41 121.1(17) . . ?
C37 C42 C41 120.0 . . ?
O9 C37 C42 109.6(18) . . ?
O9 C37 C38 129.6(18) . . ?
C38 C37 C42 120.0 . . ?
C37 C38 C39 120.0 . . ?
C40 C39 C38 120.0 . . ?
C39 C40 C41 120.0 . . ?
C40 C41 C42 120.0 . . ?
O12 C46 C45 95(3) . . ?
C32 C31 O6 129(3) . . ?
C47 C48 O5 100(2) . . ?
C48 C47 O12 104(3) . . ?
C24B C23 O4 107.9(19) . . ?
C24A C23 O4 107(2) . . ?
C43 C44 O11 114(3) . . ?
O8 C35 C36 119(2) . . ?
C46 C45 O11 95(2) . . ?
C21 C20 O2 99(2) . . ?
O4 C22 C17 119(2) . . ?
O3 C22 O4 122(3) . . ?
O3 C22 C17 119(3) . . ?
F1 B1 F2 105.1(17) . . ?
F3 B1 F1 95.4(15) . . ?
F3 B1 F2 113.1(16) . . ?
F3 B1 F4 116(2) . . ?
F4 B1 F1 96.0(14) . . ?
F4 B1 F2 124.1(18) . . ?
F8A B2 F6A 112.6(18) . . ?
F8A B2 F7A 105.7(17) . . ?
F5 B2 F8A 117.7(19) . . ?
F5 B2 F6B 116.1(18) . . ?
F5 B2 F6A 112.6(18) . . ?
F5 B2 F7B 113.1(17) . . ?
F5 B2 F8B 101.4(15) . . ?
F5 B2 F7A 102.8(15) . . ?
F6B B2 F7B 115.1(17) . . ?
F6B B2 F8B 107.0(17) . . ?
F6A B2 F7A 103.6(17) . . ?
F7B B2 F8B 101.8(15) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.563
_oxdiff_exptl_absorpt_empirical_full_min 0.657
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile - isopropyl ether'
