# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_oic327s_0m
_database_code_depnum_ccdc_archive 'CCDC 2312678'
loop_
_audit_author_name
_audit_author_address
'Craig Robertson'
;University of Sheffield
United Kingdom
;
_audit_update_record             
;
2023-12-07 deposited with the CCDC.	2024-01-23 downloaded from the CCDC.
;
_audit_creation_date             2022-04-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
a.choi@sheffield.ac.uk
Craig.robertson@sheffield.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H25 F2 N O3'
_chemical_formula_sum            'C19 H25 F2 N O3'
_chemical_formula_weight         353.40
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.496(3)
_cell_length_b                   11.821(5)
_cell_length_c                   12.772(5)
_cell_angle_alpha                73.748(8)
_cell_angle_beta                 83.671(9)
_cell_angle_gamma                75.267(8)
_cell_volume                     909.8(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.634
_cell_measurement_theta_min      2.789
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.952
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.3586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1529 before and 0.0948 after correction.
The Ratio of minimum to maximum transmission is 0.4808.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.45
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            36476
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.917
_diffrn_reflns_theta_min         1.662
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4048
_reflns_number_total             4707
_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 (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4707
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.041
_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)+(0.0562P)²+0.2658P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1173
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C)
;
_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
F1 F 0.71671(11) 0.05568(6) 0.76108(6) 0.02383(17) Uani 1 1 d . . . . .
F2 F 0.99561(10) 0.09025(6) 0.65329(6) 0.02452(17) Uani 1 1 d . . . . .
O1 O 0.85285(12) 0.08385(7) 0.08548(7) 0.01988(18) Uani 1 1 d . . . . .
O2 O 0.05533(12) 0.47736(7) 0.35556(7) 0.01872(18) Uani 1 1 d . . . . .
O3 O 0.35572(12) 0.53371(7) 0.27013(6) 0.01767(18) Uani 1 1 d . . . . .
N1 N 0.38249(13) 0.39174(8) 0.42938(7) 0.01307(18) Uani 1 1 d . . . . .
C1 C 0.61277(15) 0.35903(9) 0.39994(8) 0.0127(2) Uani 1 1 d . . . . .
H1 H 0.656810 0.436612 0.364559 0.015 Uiso 1 1 calc R U . . .
C2 C 0.74268(16) 0.29754(9) 0.50254(8) 0.0141(2) Uani 1 1 d . . . . .
H2A H 0.889206 0.259317 0.480842 0.017 Uiso 1 1 calc R U . . .
H2B H 0.752066 0.359782 0.538837 0.017 Uiso 1 1 calc R U . . .
C3 C 0.64560(16) 0.20239(9) 0.58239(8) 0.0142(2) Uani 1 1 d . . . . .
C4 C 0.42183(16) 0.25733(10) 0.61861(9) 0.0159(2) Uani 1 1 d . . . . .
H4A H 0.424283 0.321668 0.653825 0.019 Uiso 1 1 calc R U . . .
H4B H 0.361922 0.194326 0.672392 0.019 Uiso 1 1 calc R U . . .
C5 C 0.28412(16) 0.31063(10) 0.51935(8) 0.0148(2) Uani 1 1 d . . . . .
H5A H 0.260204 0.243806 0.493280 0.018 Uiso 1 1 calc R U . . .
H5B H 0.143697 0.356587 0.540996 0.018 Uiso 1 1 calc R U . . .
C6 C 0.66436(15) 0.28327(9) 0.31730(8) 0.0132(2) Uani 1 1 d . . . . .
C7 C 0.86454(16) 0.27405(10) 0.26194(9) 0.0165(2) Uani 1 1 d . . . . .
H7 H 0.962193 0.314408 0.277323 0.020 Uiso 1 1 calc R U . . .
C8 C 0.92259(17) 0.20754(10) 0.18553(9) 0.0181(2) Uani 1 1 d . . . . .
H8 H 1.058496 0.202961 0.148650 0.022 Uiso 1 1 calc R U . . .
C9 C 0.78115(16) 0.14703(9) 0.16258(8) 0.0154(2) Uani 1 1 d . . . . .
C10 C 0.58127(17) 0.15543(9) 0.21571(9) 0.0156(2) Uani 1 1 d . . . . .
H10 H 0.483890 0.114993 0.200175 0.019 Uiso 1 1 calc R U . . .
C11 C 0.52467(16) 0.22403(9) 0.29235(9) 0.0148(2) Uani 1 1 d . . . . .
H11 H 0.387562 0.230126 0.328048 0.018 Uiso 1 1 calc R U . . .
C12 C 0.71232(19) 0.02131(11) 0.05954(10) 0.0230(2) Uani 1 1 d . . . . .
H12A H 0.779562 -0.018066 0.002208 0.035 Uiso 1 1 calc R U . . .
H12B H 0.579156 0.079177 0.033761 0.035 Uiso 1 1 calc R U . . .
H12C H 0.681739 -0.040140 0.124839 0.035 Uiso 1 1 calc R U . . .
C13 C 0.69320(18) 0.07136(10) 0.56685(9) 0.0192(2) Uani 1 1 d . . . . .
H13A H 0.577611 0.027418 0.585957 0.023 Uiso 1 1 calc R U . . .
H13B H 0.790189 0.053498 0.505072 0.023 Uiso 1 1 calc R U . . .
C14 C 0.78295(17) 0.09792(10) 0.65562(9) 0.0181(2) Uani 1 1 d . . . . .
C15 C 0.24709(16) 0.46840(9) 0.35084(8) 0.0138(2) Uani 1 1 d . . . . .
C16 C 0.26108(18) 0.60235(10) 0.16447(9) 0.0183(2) Uani 1 1 d . . . . .
C17 C 0.4486(2) 0.64830(14) 0.10047(11) 0.0346(3) Uani 1 1 d . . . . .
H17A H 0.486537 0.704607 0.134438 0.052 Uiso 1 1 calc R U . . .
H17B H 0.409275 0.690250 0.025104 0.052 Uiso 1 1 calc R U . . .
H17C H 0.570800 0.579644 0.100667 0.052 Uiso 1 1 calc R U . . .
C18 C 0.1927(3) 0.51795(13) 0.11248(11) 0.0367(3) Uani 1 1 d . . . . .
H18A H 0.310111 0.446805 0.113082 0.055 Uiso 1 1 calc R U . . .
H18B H 0.154964 0.560425 0.036987 0.055 Uiso 1 1 calc R U . . .
H18C H 0.068872 0.492031 0.153734 0.055 Uiso 1 1 calc R U . . .
C19 C 0.0789(2) 0.70745(12) 0.17806(11) 0.0309(3) Uani 1 1 d . . . . .
H19A H -0.040937 0.676135 0.218439 0.046 Uiso 1 1 calc R U . . .
H19B H 0.033728 0.759245 0.106026 0.046 Uiso 1 1 calc R U . . .
H19C H 0.126305 0.754852 0.218510 0.046 Uiso 1 1 calc R 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
F1 C14 1.3615(14) . ?
F2 C14 1.3587(14) . ?
O1 C9 1.3704(13) . ?
O1 C12 1.4272(15) . ?
O2 C15 1.2192(14) . ?
O3 C15 1.3519(13) . ?
O3 C16 1.4744(13) . ?
N1 C1 1.4805(13) . ?
N1 C5 1.4768(13) . ?
N1 C15 1.3717(14) . ?
C1 H1 1.0000 . ?
C1 C2 1.5350(15) . ?
C1 C6 1.5254(15) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5099(15) . ?
C3 C4 1.5128(15) . ?
C3 C13 1.5650(16) . ?
C3 C14 1.4741(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5233(15) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.4040(15) . ?
C6 C11 1.3883(15) . ?
C7 H7 0.9500 . ?
C7 C8 1.3821(16) . ?
C8 H8 0.9500 . ?
C8 C9 1.3974(16) . ?
C9 C10 1.3907(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.4015(15) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.4705(17) . ?
C16 C17 1.5217(18) . ?
C16 C18 1.5148(19) . ?
C16 C19 1.5171(16) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
C9 O1 C12 117.20(9) . . ?
C15 O3 C16 121.71(9) . . ?
C5 N1 C1 121.02(8) . . ?
C15 N1 C1 118.65(9) . . ?
C15 N1 C5 115.51(9) . . ?
N1 C1 H1 106.9 . . ?
N1 C1 C2 110.80(8) . . ?
N1 C1 C6 113.24(8) . . ?
C2 C1 H1 106.9 . . ?
C6 C1 H1 106.9 . . ?
C6 C1 C2 111.72(8) . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
C3 C2 C1 112.34(9) . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C2 C3 C4 110.87(9) . . ?
C2 C3 C13 119.78(9) . . ?
C4 C3 C13 118.03(9) . . ?
C14 C3 C2 119.95(9) . . ?
C14 C3 C4 121.25(9) . . ?
C14 C3 C13 57.78(7) . . ?
C3 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
C3 C4 C5 109.02(9) . . ?
H4A C4 H4B 108.3 . . ?
C5 C4 H4A 109.9 . . ?
C5 C4 H4B 109.9 . . ?
N1 C5 C4 112.33(9) . . ?
N1 C5 H5A 109.1 . . ?
N1 C5 H5B 109.1 . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C1 118.02(9) . . ?
C11 C6 C1 124.09(9) . . ?
C11 C6 C7 117.88(10) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.42(10) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 119.93(10) . . ?
C9 C8 H8 120.0 . . ?
O1 C9 C8 115.61(9) . . ?
O1 C9 C10 124.59(10) . . ?
C10 C9 C8 119.79(10) . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.46(10) . . ?
C11 C10 H10 120.3 . . ?
C6 C11 C10 121.51(9) . . ?
C6 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C3 C13 H13A 118.0 . . ?
C3 C13 H13B 118.0 . . ?
H13A C13 H13B 115.1 . . ?
C14 C13 C3 58.01(7) . . ?
C14 C13 H13A 118.0 . . ?
C14 C13 H13B 118.0 . . ?
F1 C14 C3 120.09(9) . . ?
F1 C14 C13 120.08(10) . . ?
F2 C14 F1 108.22(9) . . ?
F2 C14 C3 119.57(9) . . ?
F2 C14 C13 119.35(10) . . ?
C13 C14 C3 64.21(8) . . ?
O2 C15 O3 125.46(10) . . ?
O2 C15 N1 124.11(10) . . ?
O3 C15 N1 110.41(9) . . ?
O3 C16 C17 101.43(9) . . ?
O3 C16 C18 109.92(10) . . ?
O3 C16 C19 110.88(9) . . ?
C18 C16 C17 111.17(12) . . ?
C18 C16 C19 112.26(12) . . ?
C19 C16 C17 110.67(11) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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 C9 C10 C11 -179.25(9) . . . . ?
N1 C1 C2 C3 45.39(11) . . . . ?
N1 C1 C6 C7 163.44(9) . . . . ?
N1 C1 C6 C11 -15.71(14) . . . . ?
C1 N1 C5 C4 42.41(13) . . . . ?
C1 N1 C15 O2 160.35(10) . . . . ?
C1 N1 C15 O3 -21.22(13) . . . . ?
C1 C2 C3 C4 -59.39(11) . . . . ?
C1 C2 C3 C13 83.52(11) . . . . ?
C1 C2 C3 C14 151.24(10) . . . . ?
C1 C6 C7 C8 -179.70(9) . . . . ?
C1 C6 C11 C10 -179.88(9) . . . . ?
C2 C1 C6 C7 -70.60(12) . . . . ?
C2 C1 C6 C11 110.25(11) . . . . ?
C2 C3 C4 C5 61.06(11) . . . . ?
C2 C3 C13 C14 108.62(11) . . . . ?
C2 C3 C14 F1 140.36(10) . . . . ?
C2 C3 C14 F2 2.27(15) . . . . ?
C2 C3 C14 C13 -108.33(11) . . . . ?
C3 C4 C5 N1 -50.94(12) . . . . ?
C3 C13 C14 F1 111.32(11) . . . . ?
C3 C13 C14 F2 -110.92(11) . . . . ?
C4 C3 C13 C14 -111.04(11) . . . . ?
C4 C3 C14 F1 -5.80(16) . . . . ?
C4 C3 C14 F2 -143.89(10) . . . . ?
C4 C3 C14 C13 105.51(11) . . . . ?
C5 N1 C1 C2 -38.57(12) . . . . ?
C5 N1 C1 C6 87.88(11) . . . . ?
C5 N1 C15 O2 4.66(15) . . . . ?
C5 N1 C15 O3 -176.91(8) . . . . ?
C6 C1 C2 C3 -81.89(11) . . . . ?
C6 C7 C8 C9 -0.43(16) . . . . ?
C7 C6 C11 C10 0.97(15) . . . . ?
C7 C8 C9 O1 179.82(9) . . . . ?
C7 C8 C9 C10 0.89(16) . . . . ?
C8 C9 C10 C11 -0.43(16) . . . . ?
C9 C10 C11 C6 -0.52(16) . . . . ?
C11 C6 C7 C8 -0.49(16) . . . . ?
C12 O1 C9 C8 -179.73(10) . . . . ?
C12 O1 C9 C10 -0.87(15) . . . . ?
C13 C3 C4 C5 -82.58(11) . . . . ?
C13 C3 C14 F1 -111.31(12) . . . . ?
C13 C3 C14 F2 110.60(12) . . . . ?
C14 C3 C4 C5 -150.03(10) . . . . ?
C15 O3 C16 C17 -174.85(10) . . . . ?
C15 O3 C16 C18 -57.12(14) . . . . ?
C15 O3 C16 C19 67.59(13) . . . . ?
C15 N1 C1 C2 167.12(9) . . . . ?
C15 N1 C1 C6 -66.43(12) . . . . ?
C15 N1 C5 C4 -162.53(9) . . . . ?
C16 O3 C15 O2 -15.57(16) . . . . ?
C16 O3 C15 N1 166.02(9) . . . . ?

_olex2_date_sample_data_collection 2022-04-19
_olex2_date_sample_submission    2022-03-31
_olex2_exptl_crystal_mounting_method 'Mitigen microloop in fomblin oil'
_olex2_submission_original_sample_id AC-14-18-P1
_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_oic326s_0m
_database_code_depnum_ccdc_archive 'CCDC 2312679'
loop_
_audit_author_name
_audit_author_address
'Craig Robertson'
;University of Sheffield
United Kingdom
;
_audit_update_record             
;
2023-12-07 deposited with the CCDC.	2024-01-23 downloaded from the CCDC.
;
_audit_creation_date             2022-04-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
a.choi@sheffield.ac.uk
Craig.robertson@sheffield.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H24 Cl F2 N O4'
_chemical_formula_sum            'C20 H24 Cl F2 N O4'
_chemical_formula_weight         415.85
_chemical_absolute_configuration ad
_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'
Cl Cl 0.1484 0.1585 '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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.252(7)
_cell_length_b                   10.441(11)
_cell_length_c                   12.226(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.816(10)
_cell_angle_gamma                90
_cell_volume                     1034.7(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4917
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      25.64
_cell_measurement_theta_min      2.59
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.928
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0587 before and 0.0545 after correction.
The Ratio of minimum to maximum transmission is 0.9221.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.334
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.177
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19144
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.712
_diffrn_reflns_theta_min         1.696
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                4760
_reflns_number_total             5317
_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 (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 2040 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         5317
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.025
_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)+(0.0352P)²+0.0911P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0794
_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 C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
;
_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
Cl1 Cl 1.09213(7) 0.09422(5) 0.83598(5) 0.02288(13) Uani 1 1 d . . . . .
F1 F 0.3661(2) 0.88592(15) 0.87867(14) 0.0348(4) Uani 1 1 d . . . . .
F2 F 0.60083(19) 0.81980(15) 0.97831(13) 0.0334(4) Uani 1 1 d . . . . .
O1 O 0.8829(2) 0.70153(16) 0.82435(15) 0.0231(4) Uani 1 1 d . . . . .
O2 O 0.6395(2) 0.78262(15) 0.73982(14) 0.0221(4) Uani 1 1 d . . . . .
O3 O 0.4315(2) 0.56685(18) 0.49508(13) 0.0270(4) Uani 1 1 d . . . . .
O4 O 0.69963(18) 0.59058(17) 0.58239(12) 0.0198(3) Uani 1 1 d . . . . .
N1 N 0.5103(2) 0.55139(17) 0.68458(15) 0.0155(4) Uani 1 1 d . . . . .
C1 C 0.6432(3) 0.56024(19) 0.78338(17) 0.0139(4) Uani 1 1 d . . . . .
C2 C 0.5607(3) 0.5624(2) 0.88829(18) 0.0180(5) Uani 1 1 d . . . . .
H2A H 0.521488 0.475063 0.901138 0.022 Uiso 1 1 calc R U . . .
H2B H 0.644853 0.586317 0.953979 0.022 Uiso 1 1 calc R U . . .
C3 C 0.4174(3) 0.6543(2) 0.8786(2) 0.0208(5) Uani 1 1 d . . . . .
C4 C 0.2889(3) 0.6409(2) 0.7711(2) 0.0242(5) Uani 1 1 d . . . . .
H4A H 0.179329 0.622213 0.789341 0.029 Uiso 1 1 calc R U . . .
H4B H 0.280896 0.722076 0.728605 0.029 Uiso 1 1 calc R U . . .
C5 C 0.3398(3) 0.5323(2) 0.7011(2) 0.0213(5) Uani 1 1 d . . . . .
H5A H 0.331403 0.449490 0.738980 0.026 Uiso 1 1 calc R U . . .
H5B H 0.264369 0.529677 0.627887 0.026 Uiso 1 1 calc R U . . .
C6 C 0.7595(3) 0.4442(2) 0.79366(18) 0.0146(4) Uani 1 1 d . . . . .
C7 C 0.8939(3) 0.4350(2) 0.88288(18) 0.0177(5) Uani 1 1 d . . . . .
H7 H 0.915282 0.502991 0.935243 0.021 Uiso 1 1 calc R U . . .
C8 C 0.9961(3) 0.3281(2) 0.89578(19) 0.0186(5) Uani 1 1 d . . . . .
H8 H 1.086998 0.322911 0.956124 0.022 Uiso 1 1 calc R U . . .
C9 C 0.9633(3) 0.2290(2) 0.81925(19) 0.0169(4) Uani 1 1 d . . . . .
C10 C 0.8313(3) 0.2339(2) 0.73142(19) 0.0180(5) Uani 1 1 d . . . . .
H10 H 0.810144 0.164980 0.679964 0.022 Uiso 1 1 calc R U . . .
C11 C 0.7291(3) 0.3416(2) 0.71930(19) 0.0164(4) Uani 1 1 d . . . . .
H11 H 0.637386 0.345160 0.659412 0.020 Uiso 1 1 calc R U . . .
C12 C 0.7393(3) 0.6869(2) 0.78336(18) 0.0163(4) Uani 1 1 d . . . . .
C13 C 0.7196(4) 0.9067(2) 0.7417(3) 0.0327(6) Uani 1 1 d . . . . .
H13A H 0.812169 0.900999 0.702000 0.049 Uiso 1 1 calc R U . . .
H13B H 0.760717 0.932395 0.818975 0.049 Uiso 1 1 calc R U . . .
H13C H 0.640146 0.970300 0.705236 0.049 Uiso 1 1 calc R U . . .
C14 C 0.3573(4) 0.6903(3) 0.9882(2) 0.0341(6) Uani 1 1 d . . . . .
H14A H 0.237479 0.703201 0.984480 0.041 Uiso 1 1 calc R U . . .
H14B H 0.417163 0.653296 1.058916 0.041 Uiso 1 1 calc R U . . .
C15 C 0.4449(3) 0.7823(2) 0.9301(2) 0.0260(6) Uani 1 1 d . . . . .
C16 C 0.5376(3) 0.5702(2) 0.57890(18) 0.0180(5) Uani 1 1 d . . . . .
C17 C 0.7703(3) 0.5925(3) 0.47963(18) 0.0232(5) Uani 1 1 d . . . . .
C18 C 0.9505(3) 0.6153(4) 0.5265(3) 0.0429(8) Uani 1 1 d . . . . .
H18A H 0.964371 0.700361 0.560791 0.064 Uiso 1 1 calc R U . . .
H18B H 1.013835 0.610304 0.466345 0.064 Uiso 1 1 calc R U . . .
H18C H 0.990331 0.549987 0.582685 0.064 Uiso 1 1 calc R U . . .
C19 C 0.7457(4) 0.4624(3) 0.4233(2) 0.0318(6) Uani 1 1 d . . . . .
H19A H 0.798181 0.396199 0.474930 0.048 Uiso 1 1 calc R U . . .
H19B H 0.795562 0.462613 0.356647 0.048 Uiso 1 1 calc R U . . .
H19C H 0.627373 0.444372 0.402121 0.048 Uiso 1 1 calc R U . . .
C20 C 0.6961(4) 0.7015(3) 0.4036(2) 0.0367(7) Uani 1 1 d . . . . .
H20A H 0.581132 0.681237 0.371158 0.055 Uiso 1 1 calc R U . . .
H20B H 0.759208 0.712506 0.343870 0.055 Uiso 1 1 calc R U . . .
H20C H 0.700160 0.780846 0.446820 0.055 Uiso 1 1 calc R 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
Cl1 C9 1.753(3) . ?
F1 C15 1.355(3) . ?
F2 C15 1.368(3) . ?
O1 C12 1.207(3) . ?
O2 C12 1.340(3) . ?
O2 C13 1.453(3) . ?
O3 C16 1.217(3) . ?
O4 C16 1.346(3) . ?
O4 C17 1.481(3) . ?
N1 C1 1.474(3) . ?
N1 C5 1.472(3) . ?
N1 C16 1.367(3) . ?
C1 C2 1.561(3) . ?
C1 C6 1.536(3) . ?
C1 C12 1.542(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.510(3) . ?
C3 C4 1.532(4) . ?
C3 C14 1.560(3) . ?
C3 C15 1.477(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.526(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.406(3) . ?
C6 C11 1.397(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.390(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(3) . ?
C9 C10 1.380(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.396(3) . ?
C11 H11 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.464(4) . ?
C17 C18 1.509(4) . ?
C17 C19 1.519(4) . ?
C17 C20 1.524(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
C12 O2 C13 114.5(2) . . ?
C16 O4 C17 121.46(17) . . ?
C5 N1 C1 118.63(19) . . ?
C16 N1 C1 122.45(19) . . ?
C16 N1 C5 118.72(18) . . ?
N1 C1 C2 107.62(18) . . ?
N1 C1 C6 112.02(17) . . ?
N1 C1 C12 110.92(17) . . ?
C6 C1 C2 107.83(17) . . ?
C6 C1 C12 111.27(18) . . ?
C12 C1 C2 106.93(17) . . ?
C1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 C1 113.60(18) . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C2 C3 C4 114.5(2) . . ?
C2 C3 C14 117.2(2) . . ?
C4 C3 C14 118.6(2) . . ?
C15 C3 C2 119.1(2) . . ?
C15 C3 C4 118.3(2) . . ?
C15 C3 C14 57.54(18) . . ?
C3 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
C5 C4 C3 109.2(2) . . ?
C5 C4 H4A 109.8 . . ?
C5 C4 H4B 109.8 . . ?
N1 C5 C4 110.35(19) . . ?
N1 C5 H5A 109.6 . . ?
N1 C5 H5B 109.6 . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C7 C6 C1 120.51(19) . . ?
C11 C6 C1 121.2(2) . . ?
C11 C6 C7 118.1(2) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.1(2) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 119.0(2) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 Cl1 118.86(18) . . ?
C10 C9 Cl1 119.57(17) . . ?
C10 C9 C8 121.6(2) . . ?
C9 C10 H10 120.5 . . ?
C9 C10 C11 119.0(2) . . ?
C11 C10 H10 120.5 . . ?
C6 C11 H11 119.4 . . ?
C10 C11 C6 121.2(2) . . ?
C10 C11 H11 119.4 . . ?
O1 C12 O2 123.6(2) . . ?
O1 C12 C1 125.0(2) . . ?
O2 C12 C1 111.21(19) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C14 H14A 117.9 . . ?
C3 C14 H14B 117.9 . . ?
H14A C14 H14B 115.1 . . ?
C15 C14 C3 58.35(17) . . ?
C15 C14 H14A 117.9 . . ?
C15 C14 H14B 117.9 . . ?
F1 C15 F2 107.6(2) . . ?
F1 C15 C3 120.2(2) . . ?
F1 C15 C14 120.8(2) . . ?
F2 C15 C3 120.0(2) . . ?
F2 C15 C14 119.3(2) . . ?
C14 C15 C3 64.10(18) . . ?
O3 C16 O4 125.8(2) . . ?
O3 C16 N1 124.9(2) . . ?
O4 C16 N1 109.37(18) . . ?
O4 C17 C18 101.36(19) . . ?
O4 C17 C19 109.4(2) . . ?
O4 C17 C20 110.5(2) . . ?
C18 C17 C19 110.6(2) . . ?
C18 C17 C20 111.6(3) . . ?
C19 C17 C20 112.8(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
Cl1 C9 C10 C11 179.74(17) . . . . ?
N1 C1 C2 C3 -46.9(2) . . . . ?
N1 C1 C6 C7 -179.83(19) . . . . ?
N1 C1 C6 C11 -4.0(3) . . . . ?
N1 C1 C12 O1 -150.3(2) . . . . ?
N1 C1 C12 O2 34.8(2) . . . . ?
C1 N1 C5 C4 58.3(3) . . . . ?
C1 N1 C16 O3 -178.2(2) . . . . ?
C1 N1 C16 O4 2.8(3) . . . . ?
C1 C2 C3 C4 50.2(3) . . . . ?
C1 C2 C3 C14 -164.3(2) . . . . ?
C1 C2 C3 C15 -98.1(3) . . . . ?
C1 C6 C7 C8 177.3(2) . . . . ?
C1 C6 C11 C10 -177.4(2) . . . . ?
C2 C1 C6 C7 -61.6(3) . . . . ?
C2 C1 C6 C11 114.3(2) . . . . ?
C2 C1 C12 O1 92.6(3) . . . . ?
C2 C1 C12 O2 -82.3(2) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C2 C3 C14 C15 108.7(3) . . . . ?
C2 C3 C15 F1 142.6(2) . . . . ?
C2 C3 C15 F2 5.0(4) . . . . ?
C2 C3 C15 C14 -105.4(3) . . . . ?
C3 C4 C5 N1 -52.8(3) . . . . ?
C3 C14 C15 F1 111.2(3) . . . . ?
C3 C14 C15 F2 -111.4(2) . . . . ?
C4 C3 C14 C15 -107.1(3) . . . . ?
C4 C3 C15 F1 -4.5(4) . . . . ?
C4 C3 C15 F2 -142.1(2) . . . . ?
C4 C3 C15 C14 107.5(3) . . . . ?
C5 N1 C1 C2 -6.6(2) . . . . ?
C5 N1 C1 C6 111.7(2) . . . . ?
C5 N1 C1 C12 -123.3(2) . . . . ?
C5 N1 C16 O3 -3.5(3) . . . . ?
C5 N1 C16 O4 177.57(18) . . . . ?
C6 C1 C2 C3 -167.92(19) . . . . ?
C6 C1 C12 O1 -24.9(3) . . . . ?
C6 C1 C12 O2 160.21(18) . . . . ?
C6 C7 C8 C9 -0.4(3) . . . . ?
C7 C6 C11 C10 -1.4(3) . . . . ?
C7 C8 C9 Cl1 -179.87(17) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C9 C10 C11 C6 0.6(3) . . . . ?
C11 C6 C7 C8 1.3(3) . . . . ?
C12 C1 C2 C3 72.3(2) . . . . ?
C12 C1 C6 C7 55.4(3) . . . . ?
C12 C1 C6 C11 -128.8(2) . . . . ?
C13 O2 C12 O1 2.3(3) . . . . ?
C13 O2 C12 C1 177.3(2) . . . . ?
C14 C3 C4 C5 -143.8(2) . . . . ?
C14 C3 C15 F1 -112.0(3) . . . . ?
C14 C3 C15 F2 110.4(3) . . . . ?
C15 C3 C4 C5 149.8(2) . . . . ?
C16 O4 C17 C18 -178.9(2) . . . . ?
C16 O4 C17 C19 -62.1(3) . . . . ?
C16 O4 C17 C20 62.7(3) . . . . ?
C16 N1 C1 C2 168.12(18) . . . . ?
C16 N1 C1 C6 -73.5(2) . . . . ?
C16 N1 C1 C12 51.5(3) . . . . ?
C16 N1 C5 C4 -116.6(2) . . . . ?
C17 O4 C16 O3 -9.3(3) . . . . ?
C17 O4 C16 N1 169.7(2) . . . . ?

_olex2_date_sample_data_collection 2022-03-30
_olex2_date_sample_submission    2022-03-29
_olex2_exptl_crystal_mounting_method 'Mitigen microloop in fomblin oil'
_olex2_submission_original_sample_id AC-14-87-P1
_olex2_submission_special_instructions 'No special instructions were received'
