# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1972801'
_audit_update_record             
;
2019-12-18 deposited with the CCDC.	2020-02-10 downloaded from the CCDC.
;
_audit_creation_date             2019-12-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C31 H25 F6 N O6'
_chemical_formula_sum            'C31 H25 F6 N O6'
_chemical_formula_weight         621.52
_chemical_absolute_configuration s
_chemical_melting_point          ?
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'
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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.105(5)
_cell_length_b                   11.571(5)
_cell_length_c                   27.397(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2886(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9827
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.180
_cell_measurement_theta_min      2.686
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            67450
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         26.760
_diffrn_reflns_theta_min         2.686
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_source                   ?
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4152
_reflns_number_total             6161
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 1524 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         6161
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0608
_refine_ls_restrained_S_all      1.049
_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)+(0.0916P)²+1.3554P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1594
_refine_ls_wR_factor_ref         0.1962
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H38 of C38, H40 of C40, H37 of C37, H33 of C33, H41 of
  C41, H32 of C32, H42 of C42, H31 of C31, H21 of C21, H8 of C8, H9 of C9, H1
  of C1, H20 of C20, H28 of C28, H10 of C10, H24 of C24, H26 of C26
 At 1.5 times of:
  All O(H) groups, H4 of C42
2.a Everything fixed:
 H4
2.b Ternary CH refined with riding coordinates:
 C24(H24), C33(H33)
2.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
2.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C8(H8), C9(H9), C10(H10), C20(H20), C21(H21), C26(H26), C28(H28),
 C31(H31), C32(H32), C37(H37), C38(H38), C40(H40), C41(H41), C42(H42)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 -0.3414(5) -0.5031(4) 0.05768(13) 0.0595(10) Uani 1 1 d . . . . .
C1 C -0.0391(6) -0.5434(5) 0.0356(2) 0.0721(14) Uani 1 1 d . . . . .
H1 H -0.086280 -0.477726 0.023910 0.087 Uiso 1 1 calc R . . . .
O1 O -0.8422(6) 0.0933(3) 0.17697(16) 0.0882(13) Uani 1 1 d . . . . .
F1 F -1.0850(9) -0.3461(4) -0.3030(2) 0.204(4) Uani 1 1 d . . . . .
F4 F -1.0222(11) -0.2124(7) -0.34566(19) 0.218(4) Uani 1 1 d . . . . .
C2 C -0.1096(6) -0.6142(4) 0.06822(18) 0.0596(12) Uani 1 1 d . . . . .
F2 F -1.0550(5) 0.0156(4) 0.33748(13) 0.1114(14) Uani 1 1 d . . . . .
O2 O -1.0040(6) 0.1250(3) 0.24990(17) 0.0917(13) Uani 1 1 d . . . . .
H2 H -0.944377 0.144435 0.229031 0.138 Uiso 1 1 calc GR . . . .
C3 C -0.2640(6) -0.5908(5) 0.08572(19) 0.0646(13) Uani 1 1 d . . . . .
H3A H -0.319608 -0.662241 0.084370 0.077 Uiso 1 1 calc R . . . .
H3B H -0.260023 -0.566514 0.119581 0.077 Uiso 1 1 calc R . . . .
O3 O -0.8135(5) -0.1025(3) -0.18962(14) 0.0740(11) Uani 1 1 d . . . . .
F3 F -1.0967(7) -0.1419(3) 0.30001(17) 0.136(2) Uani 1 1 d . . . . .
O4 O -0.9722(5) -0.0795(3) -0.26462(14) 0.0789(11) Uani 1 1 d . . . . .
C4 C -0.3848(6) -0.5397(5) 0.00882(17) 0.0627(13) Uani 1 1 d . . . . .
H4A H -0.439670 -0.611562 0.009727 0.075 Uiso 1 1 calc R . . . .
H4B H -0.300170 -0.548976 -0.012315 0.075 Uiso 1 1 calc R . . . .
C5 C -0.4818(6) -0.4694(5) 0.07966(17) 0.0657(13) Uani 1 1 d . . . . .
H5A H -0.466320 -0.421829 0.108353 0.079 Uiso 1 1 calc R . . . .
H5B H -0.538713 -0.536870 0.088799 0.079 Uiso 1 1 calc R . . . .
F5 F -1.2362(5) 0.0022(6) 0.29119(19) 0.1319(17) Uani 1 1 d . . . . .
O5 O -0.5778(4) -0.4835(3) -0.04429(11) 0.0621(9) Uani 1 1 d . . . . .
O6 O -0.5395(4) -0.2783(3) 0.04476(12) 0.0640(9) Uani 1 1 d . . . . .
F6 F -1.1967(9) -0.1973(8) -0.3079(4) 0.218(4) Uani 1 1 d . . . . .
C7 C -0.6359(5) -0.4116(4) -0.07839(15) 0.0518(10) Uani 1 1 d . . . . .
C8 C -0.6296(6) -0.2919(4) -0.07727(18) 0.0616(13) Uani 1 1 d . . . . .
H8 H -0.583608 -0.254337 -0.051454 0.074 Uiso 1 1 calc R . . . .
C9 C -0.7085(6) -0.4676(5) -0.11651(17) 0.0624(13) Uani 1 1 d . . . . .
H9 H -0.713889 -0.547804 -0.117198 0.075 Uiso 1 1 calc R . . . .
C10 C -0.7717(6) -0.4034(4) -0.15292(18) 0.0607(12) Uani 1 1 d . . . . .
H10 H -0.821062 -0.440888 -0.178077 0.073 Uiso 1 1 calc R . . . .
C11 C -0.7635(5) -0.2833(4) -0.15302(16) 0.0509(10) Uani 1 1 d . . . . .
C12 C -0.8323(6) -0.2141(4) -0.19143(17) 0.0562(11) Uani 1 1 d . . . . .
C15 C -0.9823(6) -0.1883(4) -0.26338(18) 0.0645(13) Uani 1 1 d . . . . .
C19 C -0.8504(6) -0.0175(4) 0.18377(19) 0.0630(13) Uani 1 1 d . . . . .
C20 C -0.6920(6) -0.2289(4) -0.11467(18) 0.0602(12) Uani 1 1 d . . . . .
H20 H -0.686029 -0.148690 -0.114148 0.072 Uiso 1 1 calc R . . . .
C21 C -0.9169(6) -0.2602(4) -0.22877(17) 0.0625(12) Uani 1 1 d . . . . .
H21 H -0.930168 -0.339787 -0.230752 0.075 Uiso 1 1 calc R . . . .
C22 C -1.0691(8) -0.2417(6) -0.3038(2) 0.0866(19) Uani 1 1 d . . . . .
C24 C -0.5586(5) -0.4013(4) 0.03955(17) 0.0569(11) Uani 1 1 d . . . . .
H24 H -0.663175 -0.421036 0.038253 0.068 Uiso 1 1 calc R . . . .
C25 C -0.6188(5) -0.2235(4) 0.08018(17) 0.0569(12) Uani 1 1 d . . . . .
C26 C -0.7191(6) -0.2741(5) 0.1113(2) 0.0674(14) Uani 1 1 d . . . . .
H26 H -0.737443 -0.353013 0.109109 0.081 Uiso 1 1 calc R . . . .
C27 C -0.7701(6) -0.0896(4) 0.14838(18) 0.0578(12) Uani 1 1 d . . . . .
C28 C -0.5939(6) -0.1058(5) 0.08356(18) 0.0657(13) Uani 1 1 d . . . . .
H28 H -0.525556 -0.071130 0.063027 0.079 Uiso 1 1 calc R . . . .
C29 C -1.0051(6) 0.0140(4) 0.25360(19) 0.0662(13) Uani 1 1 d . . . . .
C30 C -1.0961(8) -0.0309(5) 0.2954(2) 0.0777(16) Uani 1 1 d . . . . .
C31 C -0.7922(6) -0.2086(4) 0.1454(2) 0.0643(13) Uani 1 1 d . . . . .
H31 H -0.857349 -0.244245 0.166803 0.077 Uiso 1 1 calc R . . . .
C32 C -0.9324(6) -0.0603(4) 0.22298(19) 0.0645(13) Uani 1 1 d . . . . .
H32 H -0.937674 -0.139569 0.228316 0.077 Uiso 1 1 calc R . . . .
C33 C -0.4802(5) -0.4403(5) -0.00746(16) 0.0576(12) Uani 1 1 d . . . . .
H33 H -0.419631 -0.377481 -0.020556 0.069 Uiso 1 1 calc R . . . .
C37 C -0.6689(6) -0.0397(5) 0.11691(19) 0.0661(13) Uani 1 1 d . . . . .
H37 H -0.651747 0.039481 0.118410 0.079 Uiso 1 1 calc R . . . .
C38 C -0.0318(8) -0.7071(5) 0.0869(2) 0.0733(15) Uani 1 1 d . . . . .
H38 H -0.076616 -0.754879 0.109766 0.088 Uiso 1 1 calc R . . . .
C40 C 0.1083(9) -0.7303(6) 0.0727(3) 0.0888(19) Uani 1 1 d . . . . .
H40 H 0.158388 -0.792411 0.086382 0.107 Uiso 1 1 calc R . . . .
C41 C 0.1019(7) -0.5689(7) 0.0201(2) 0.0861(19) Uani 1 1 d . . . . .
H41 H 0.147378 -0.522045 -0.002960 0.103 Uiso 1 1 calc R . . . .
C42 C 0.1754(8) -0.6633(7) 0.0386(3) 0.0916(19) Uani 1 1 d . . . . .
H42 H 0.269698 -0.680960 0.027973 0.110 Uiso 1 1 calc R . . . .
H4 H -0.916000 -0.055880 -0.242170 0.137 Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C3 1.455(6) . ?
N1 C4 1.458(6) . ?
N1 C5 1.466(7) . ?
C1 C2 1.372(7) . ?
C1 C41 1.384(9) . ?
O1 C19 1.297(6) . ?
F1 C22 1.217(8) . ?
F4 C22 1.270(9) . ?
C2 C3 1.510(8) . ?
C2 C38 1.385(8) . ?
F2 C30 1.327(7) . ?
O2 C29 1.288(6) . ?
O3 C12 1.305(6) . ?
F3 C30 1.290(7) . ?
O4 C15 1.262(6) . ?
C4 C33 1.509(7) . ?
C5 C24 1.523(7) . ?
F5 C30 1.337(8) . ?
O5 C7 1.358(5) . ?
O5 C33 1.435(5) . ?
O6 C24 1.440(6) . ?
O6 C25 1.366(6) . ?
F6 C22 1.276(10) . ?
C7 C8 1.386(7) . ?
C7 C9 1.395(6) . ?
C8 C20 1.380(7) . ?
C9 C10 1.370(7) . ?
C10 C11 1.392(7) . ?
C11 C12 1.463(7) . ?
C11 C20 1.387(7) . ?
C12 C21 1.387(7) . ?
C15 C21 1.395(7) . ?
C15 C22 1.494(8) . ?
C19 C27 1.474(7) . ?
C19 C32 1.399(7) . ?
C24 C33 1.540(7) . ?
C25 C26 1.379(7) . ?
C25 C28 1.383(7) . ?
C26 C31 1.376(7) . ?
C27 C31 1.394(7) . ?
C27 C37 1.388(7) . ?
C28 C37 1.374(8) . ?
C29 C30 1.506(8) . ?
C29 C32 1.372(7) . ?
C38 C40 1.361(10) . ?
C40 C42 1.358(10) . ?
C41 C42 1.378(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
C3 N1 C4 114.4(4) . . ?
C3 N1 C5 113.0(4) . . ?
C4 N1 C5 102.6(4) . . ?
C2 C1 C41 120.4(6) . . ?
C1 C2 C3 122.4(5) . . ?
C1 C2 C38 117.7(6) . . ?
C38 C2 C3 119.9(5) . . ?
N1 C3 C2 114.1(4) . . ?
N1 C4 C33 101.9(4) . . ?
N1 C5 C24 104.0(4) . . ?
C7 O5 C33 120.7(4) . . ?
C25 O6 C24 117.7(4) . . ?
O5 C7 C8 125.5(4) . . ?
O5 C7 C9 114.5(4) . . ?
C8 C7 C9 120.0(4) . . ?
C20 C8 C7 119.6(4) . . ?
C10 C9 C7 119.5(5) . . ?
C9 C10 C11 121.3(5) . . ?
C10 C11 C12 121.6(4) . . ?
C20 C11 C10 118.5(5) . . ?
C20 C11 C12 119.9(4) . . ?
O3 C12 C11 117.3(4) . . ?
O3 C12 C21 118.8(5) . . ?
C21 C12 C11 123.9(4) . . ?
O4 C15 C21 125.6(5) . . ?
O4 C15 C22 115.6(5) . . ?
C21 C15 C22 118.8(5) . . ?
O1 C19 C27 115.9(5) . . ?
O1 C19 C32 119.4(5) . . ?
C32 C19 C27 124.7(4) . . ?
C8 C20 C11 121.1(5) . . ?
C12 C21 C15 120.6(5) . . ?
F1 C22 F4 108.7(8) . . ?
F1 C22 F6 107.0(8) . . ?
F1 C22 C15 117.5(5) . . ?
F4 C22 F6 96.9(7) . . ?
F4 C22 C15 112.4(6) . . ?
F6 C22 C15 112.3(7) . . ?
C5 C24 C33 103.8(4) . . ?
O6 C24 C5 112.6(4) . . ?
O6 C24 C33 108.4(4) . . ?
O6 C25 C26 126.3(5) . . ?
O6 C25 C28 114.7(4) . . ?
C26 C25 C28 119.0(5) . . ?
C31 C26 C25 120.4(5) . . ?
C31 C27 C19 121.7(5) . . ?
C37 C27 C19 120.1(5) . . ?
C37 C27 C31 118.1(5) . . ?
C37 C28 C25 120.8(5) . . ?
O2 C29 C30 114.1(5) . . ?
O2 C29 C32 125.0(5) . . ?
C32 C29 C30 120.9(5) . . ?
F2 C30 F5 103.2(5) . . ?
F2 C30 C29 111.4(5) . . ?
F3 C30 F2 108.7(5) . . ?
F3 C30 F5 106.9(6) . . ?
F3 C30 C29 114.9(5) . . ?
F5 C30 C29 111.1(5) . . ?
C26 C31 C27 120.9(5) . . ?
C29 C32 C19 120.3(5) . . ?
C4 C33 C24 104.1(4) . . ?
O5 C33 C4 107.3(4) . . ?
O5 C33 C24 113.8(4) . . ?
C28 C37 C27 120.7(5) . . ?
C40 C38 C2 121.8(6) . . ?
C42 C40 C38 120.3(7) . . ?
C42 C41 C1 120.4(7) . . ?
C40 C42 C41 119.2(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1972802'
_audit_update_record             
;
2019-12-31 deposited with the CCDC.	2020-02-10 downloaded from the CCDC.
;
_audit_creation_date             2019-12-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C31 H25 F6 N O6'
_chemical_formula_sum            'C31 H25 F6 N O6'
_chemical_formula_weight         621.52
_chemical_absolute_configuration s
_chemical_melting_point          ?
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'
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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.103(5)
_cell_length_b                   11.578(5)
_cell_length_c                   27.425(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2890(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.694
_cell_measurement_theta_min      2.686
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            65895
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         26.794
_diffrn_reflns_theta_min         2.686
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_source                   ?
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3832
_reflns_number_total             6165
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1359 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         6165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1087
_refine_ls_R_factor_gt           0.0600
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0808P)²+1.5561P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1513
_refine_ls_wR_factor_ref         0.1888
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Everything fixed:
 H2
2.b Ternary CH refined with riding coordinates:
 C13(H13), C45(H45)
2.c Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
2.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C7(H7), C11(H11), C20(H20), C22(H22), C24(H24), C39(H39),
 C40(H40), C41(H41), C42(H42), C50(H50), C51(H51), C52(H52), C53(H53)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
C1 C -0.9603(7) 0.0434(5) -0.0356(2) 0.0731(15) Uani 1 1 d . . . . .
H1 H -0.913249 -0.022276 -0.023824 0.088 Uiso 1 1 calc R . . . .
N1 N -0.6581(5) 0.0029(4) -0.05766(14) 0.0596(11) Uani 1 1 d . . . . .
O1 O -0.1858(5) -0.3978(3) 0.18948(14) 0.0753(11) Uani 1 1 d . . . . .
F1 F 0.2363(5) -0.5016(6) -0.29129(19) 0.1353(18) Uani 1 1 d . . . . .
O2 O -0.0277(5) -0.4205(3) 0.26459(14) 0.0810(12) Uani 1 1 d . . . . .
H2 H -0.067870 -0.457870 0.241940 0.122 Uiso 1 1 d . . . . .
C2 C -0.2070(7) -0.2916(5) -0.1453(2) 0.0649(14) Uani 1 1 d . . . . .
H2A H -0.141298 -0.255955 -0.166447 0.078 Uiso 1 1 calc R . . . .
F2 F 0.0548(6) -0.5155(4) -0.33761(13) 0.1123(14) Uani 1 1 d . . . . .
O3 O -0.4216(4) -0.0166(3) 0.04424(12) 0.0632(9) Uani 1 1 d . . . . .
C3 C -0.8898(6) 0.1144(5) -0.06816(18) 0.0595(13) Uani 1 1 d . . . . .
F3 F 0.0962(7) -0.3579(4) -0.30009(17) 0.138(2) Uani 1 1 d . . . . .
C4 C -0.7358(6) 0.0910(5) -0.08571(19) 0.0652(14) Uani 1 1 d . . . . .
H4A H -0.739992 0.066881 -0.119551 0.078 Uiso 1 1 calc R . . . .
H4B H -0.680121 0.162375 -0.084337 0.078 Uiso 1 1 calc R . . . .
O4 O -0.4596(4) -0.2218(3) -0.04477(12) 0.0651(9) Uani 1 1 d . . . . .
F4 F 0.0857(9) -0.1543(4) 0.3030(2) 0.206(4) Uani 1 1 d . . . . .
C5 C -0.5174(6) -0.0308(5) -0.07961(17) 0.0667(14) Uani 1 1 d . . . . .
H5A H -0.460496 0.036627 -0.088774 0.080 Uiso 1 1 calc R . . . .
H5B H -0.532654 -0.078509 -0.108248 0.080 Uiso 1 1 calc R . . . .
O5 O 0.0040(6) -0.6249(4) -0.25007(17) 0.0934(14) Uani 1 1 d . . . . .
H5 H -0.054706 -0.644245 -0.228908 0.140 Uiso 1 1 calc GR . . . .
F5 F 0.1967(9) -0.3024(8) 0.3079(4) 0.220(4) Uani 1 1 d . . . . .
C6 C -0.6144(6) 0.0399(5) -0.00884(17) 0.0631(14) Uani 1 1 d . . . . .
H6A H -0.698952 0.049540 0.012295 0.076 Uiso 1 1 calc R . . . .
H6B H -0.559163 0.111499 -0.009865 0.076 Uiso 1 1 calc R . . . .
F6 F 0.0221(11) -0.2872(7) 0.34548(19) 0.221(4) Uani 1 1 d . . . . .
C7 C -0.3074(6) -0.2711(5) 0.11473(19) 0.0613(13) Uani 1 1 d . . . . .
H7 H -0.313291 -0.351284 0.114250 0.074 Uiso 1 1 calc R . . . .
C8 C -0.3632(5) -0.0884(4) 0.07833(15) 0.0517(11) Uani 1 1 d . . . . .
C9 C -0.1676(6) -0.2858(4) 0.19153(18) 0.0571(12) Uani 1 1 d . . . . .
C10 C -0.3805(6) -0.2765(5) -0.08015(17) 0.0581(13) Uani 1 1 d . . . . .
C11 C -0.2811(7) -0.2259(5) -0.1111(2) 0.0681(15) Uani 1 1 d . . . . .
H11 H -0.263415 -0.146930 -0.109030 0.082 Uiso 1 1 calc R . . . .
C12 C -0.2295(6) -0.4108(4) -0.14839(18) 0.0577(13) Uani 1 1 d . . . . .
C13 C -0.5195(6) -0.0598(5) 0.00744(16) 0.0576(12) Uani 1 1 d . . . . .
H13 H -0.580182 -0.122528 0.020477 0.069 Uiso 1 1 calc R . . . .
C14 C -0.2361(6) -0.2166(4) 0.15306(17) 0.0514(11) Uani 1 1 d . . . . .
C15 C -0.0175(7) -0.3118(5) 0.26346(19) 0.0659(14) Uani 1 1 d . . . . .
O18 O -0.1575(6) -0.5932(3) -0.17694(16) 0.0908(14) Uani 1 1 d . . . . .
C19 C -0.1496(6) -0.4825(4) -0.1837(2) 0.0642(14) Uani 1 1 d . . . . .
C20 C -0.0674(6) -0.4393(5) -0.22298(19) 0.0652(14) Uani 1 1 d . . . . .
H20 H -0.062015 -0.360069 -0.228255 0.078 Uiso 1 1 calc R . . . .
C22 C -0.2910(6) -0.0324(5) 0.11652(18) 0.0621(14) Uani 1 1 d . . . . .
H22 H -0.285707 0.047809 0.117195 0.074 Uiso 1 1 calc R . . . .
C24 C -0.3697(7) -0.2082(5) 0.07721(18) 0.0619(14) Uani 1 1 d . . . . .
H24 H -0.415701 -0.245764 0.051418 0.074 Uiso 1 1 calc R . . . .
C37 C 0.0053(7) -0.5140(5) -0.2537(2) 0.0681(14) Uani 1 1 d . . . . .
C39 C -0.9671(8) 0.2071(5) -0.0869(2) 0.0742(16) Uani 1 1 d . . . . .
H39 H -0.922135 0.254644 -0.109804 0.089 Uiso 1 1 calc R . . . .
C40 C -1.1080(9) 0.2307(6) -0.0727(3) 0.090(2) Uani 1 1 d . . . . .
H40 H -1.158278 0.292590 -0.086449 0.108 Uiso 1 1 calc R . . . .
C41 C -1.1747(8) 0.1637(7) -0.0385(3) 0.092(2) Uani 1 1 d . . . . .
H41 H -1.268795 0.181463 -0.027682 0.110 Uiso 1 1 calc R . . . .
C42 C -1.1015(8) 0.0695(7) -0.0202(2) 0.087(2) Uani 1 1 d . . . . .
H42 H -1.147228 0.022626 0.002781 0.104 Uiso 1 1 calc R . . . .
C45 C -0.4408(6) -0.0985(4) -0.03955(17) 0.0577(12) Uani 1 1 d . . . . .
H45 H -0.336243 -0.078585 -0.038204 0.069 Uiso 1 1 calc R . . . .
C50 C -0.2279(6) -0.0965(5) 0.15307(18) 0.0618(14) Uani 1 1 d . . . . .
H50 H -0.178878 -0.059114 0.178268 0.074 Uiso 1 1 calc R . . . .
C51 C -0.0826(6) -0.2402(5) 0.22885(18) 0.0643(14) Uani 1 1 d . . . . .
H51 H -0.068837 -0.160695 0.230777 0.077 Uiso 1 1 calc R . . . .
C52 C -0.4053(6) -0.3941(5) -0.08372(19) 0.0656(14) Uani 1 1 d . . . . .
H52 H -0.473822 -0.428996 -0.063336 0.079 Uiso 1 1 calc R . . . .
C53 C -0.3301(6) -0.4598(5) -0.11690(19) 0.0657(14) Uani 1 1 d . . . . .
H53 H -0.347044 -0.538956 -0.118250 0.079 Uiso 1 1 calc R . . . .
C54 C 0.0689(9) -0.2589(6) 0.3036(3) 0.089(2) Uani 1 1 d . . . . .
C55 C 0.0957(8) -0.4686(6) -0.2957(2) 0.0781(17) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.373(7) . ?
C1 C42 1.386(9) . ?
N1 C4 1.461(7) . ?
N1 C5 1.468(7) . ?
N1 C6 1.461(6) . ?
O1 C9 1.309(6) . ?
F1 C55 1.341(8) . ?
O2 C15 1.263(6) . ?
C2 C11 1.383(8) . ?
C2 C12 1.398(7) . ?
F2 C55 1.325(7) . ?
O3 C8 1.360(6) . ?
O3 C13 1.436(5) . ?
C3 C4 1.506(8) . ?
C3 C39 1.383(8) . ?
F3 C55 1.288(7) . ?
O4 C10 1.365(6) . ?
O4 C45 1.444(6) . ?
F4 C54 1.221(8) . ?
C5 C45 1.519(7) . ?
O5 C37 1.288(6) . ?
F5 C54 1.273(10) . ?
C6 C13 1.510(8) . ?
F6 C54 1.267(9) . ?
C7 C14 1.387(7) . ?
C7 C24 1.383(7) . ?
C8 C22 1.396(7) . ?
C8 C24 1.388(7) . ?
C9 C14 1.464(7) . ?
C9 C51 1.388(7) . ?
C10 C11 1.372(8) . ?
C10 C52 1.384(8) . ?
C12 C19 1.469(8) . ?
C12 C53 1.381(7) . ?
C13 C45 1.541(7) . ?
C14 C50 1.392(7) . ?
C15 C51 1.392(7) . ?
C15 C54 1.485(8) . ?
O18 C19 1.297(6) . ?
C19 C20 1.403(8) . ?
C20 C37 1.377(8) . ?
C22 C50 1.373(7) . ?
C37 C55 1.509(9) . ?
C39 C40 1.368(10) . ?
C40 C41 1.359(10) . ?
C41 C42 1.373(10) . ?
C52 C53 1.369(8) . ?

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
C3 C1 C42 120.1(6) . . ?
C4 N1 C5 113.1(4) . . ?
C4 N1 C6 114.2(4) . . ?
C6 N1 C5 102.5(4) . . ?
C11 C2 C12 120.9(5) . . ?
C8 O3 C13 120.8(4) . . ?
C1 C3 C4 122.4(5) . . ?
C1 C3 C39 117.9(6) . . ?
C39 C3 C4 119.6(5) . . ?
N1 C4 C3 114.1(4) . . ?
C10 O4 C45 117.8(4) . . ?
N1 C5 C45 103.9(4) . . ?
N1 C6 C13 101.7(4) . . ?
C24 C7 C14 121.1(5) . . ?
O3 C8 C22 114.5(4) . . ?
O3 C8 C24 125.4(4) . . ?
C24 C8 C22 120.1(5) . . ?
O1 C9 C14 117.2(4) . . ?
O1 C9 C51 118.6(5) . . ?
C51 C9 C14 124.2(5) . . ?
O4 C10 C11 126.1(5) . . ?
O4 C10 C52 114.9(5) . . ?
C11 C10 C52 119.0(5) . . ?
C10 C11 C2 120.4(5) . . ?
C2 C12 C19 121.7(5) . . ?
C53 C12 C2 117.7(5) . . ?
C53 C12 C19 120.6(5) . . ?
O3 C13 C6 107.2(4) . . ?
O3 C13 C45 113.6(4) . . ?
C6 C13 C45 103.9(4) . . ?
C7 C14 C9 119.8(5) . . ?
C7 C14 C50 118.6(5) . . ?
C50 C14 C9 121.5(4) . . ?
O2 C15 C51 125.4(5) . . ?
O2 C15 C54 115.6(5) . . ?
C51 C15 C54 119.0(5) . . ?
O18 C19 C12 115.9(5) . . ?
O18 C19 C20 119.5(5) . . ?
C20 C19 C12 124.7(5) . . ?
C37 C20 C19 120.1(5) . . ?
C50 C22 C8 119.5(5) . . ?
C7 C24 C8 119.5(5) . . ?
O5 C37 C20 125.0(6) . . ?
O5 C37 C55 114.3(5) . . ?
C20 C37 C55 120.7(5) . . ?
C40 C39 C3 121.8(6) . . ?
C41 C40 C39 120.0(7) . . ?
C40 C41 C42 119.3(7) . . ?
C41 C42 C1 120.8(7) . . ?
O4 C45 C5 112.6(4) . . ?
O4 C45 C13 108.4(4) . . ?
C5 C45 C13 104.0(4) . . ?
C22 C50 C14 121.2(5) . . ?
C9 C51 C15 120.9(5) . . ?
C53 C52 C10 120.8(5) . . ?
C52 C53 C12 121.3(5) . . ?
F4 C54 F5 106.2(8) . . ?
F4 C54 F6 108.1(8) . . ?
F4 C54 C15 117.7(5) . . ?
F5 C54 C15 112.9(7) . . ?
F6 C54 F5 97.0(7) . . ?
F6 C54 C15 112.8(7) . . ?
F1 C55 C37 110.7(5) . . ?
F2 C55 F1 103.3(5) . . ?
F2 C55 C37 111.5(6) . . ?
F3 C55 F1 106.8(7) . . ?
F3 C55 F2 109.1(6) . . ?
F3 C55 C37 114.8(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
