# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 2219308'
loop_
_audit_author_name
_audit_author_address
'Sizwe Zamisa'
;University of KwaZulu Natal
South Africa
;
_audit_update_record             
;
2023-04-12 deposited with the CCDC.	2023-07-12 downloaded from the CCDC.
;
_audit_creation_date             2023-04-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H22 F N3 O2'
_chemical_formula_sum            'C25 H22 F N3 O2'
_chemical_formula_weight         415.45
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.0927(4)
_cell_length_b                   7.3784(2)
_cell_length_c                   21.8294(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.390(2)
_cell_angle_gamma                90
_cell_volume                     1944.32(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3227
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.43
_cell_measurement_theta_min      2.91
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13125
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.452
_diffrn_reflns_theta_min         1.687
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2987
_reflns_number_total             3863
_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-plus (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3863
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.033
_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)+(0.0438P)²+0.7481P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0995
_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. Restrained distances
 N3-H3
 0.88 with sigma of 0.001
 F1-C13 \\sim F2-C17
 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
F2 \\sim C17: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
4. Others
 Fixed Sof: H13(0.09) H17(0.91) F1(0.95) F2(0.05)
5.a Ternary CH refined with riding coordinates:
 C7(H7)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C4(H4a,H4b)
5.c Me refined with riding coordinates:
 C18(H18a,H18b,H18c), C19(H19a,H19b,H19c)
5.d Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C21(H21),
 C22(H22), C23(H23), C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.10664(12) 0.7465(2) 1.03986(7) 0.0140(3) Uani 1 1 d . . . . .
C2 C 0.05999(13) 0.6295(2) 1.08785(7) 0.0152(3) Uani 1 1 d . . . . .
H2A H 0.088529 0.504484 1.084128 0.018 Uiso 1 1 calc R U . . .
H2B H -0.021697 0.625448 1.081409 0.018 Uiso 1 1 calc R U . . .
C3 C 0.09162(13) 0.7026(2) 1.15242(7) 0.0155(3) Uani 1 1 d . . . . .
C4 C 0.05826(13) 0.9031(2) 1.15414(7) 0.0174(4) Uani 1 1 d . . . . .
H4A H -0.023423 0.910360 1.154718 0.021 Uiso 1 1 calc R U . . .
H4B H 0.089691 0.956506 1.192967 0.021 Uiso 1 1 calc R U . . .
C5 C 0.09485(13) 1.0171(2) 1.10129(8) 0.0161(4) Uani 1 1 d . . . . .
C6 C 0.12414(12) 0.9252(2) 1.04491(7) 0.0141(3) Uani 1 1 d . . . . .
C7 C 0.17903(12) 1.0355(2) 0.99664(7) 0.0136(3) Uani 1 1 d . . . . .
H7 H 0.128987 1.138877 0.984390 0.016 Uiso 1 1 calc R U . . .
C8 C 0.19346(12) 0.9192(2) 0.94047(7) 0.0134(3) Uani 1 1 d . . . . .
C9 C 0.23398(12) 0.9848(2) 0.88522(7) 0.0145(3) Uani 1 1 d . . . . .
C10 C 0.22841(14) 0.7011(2) 0.84523(7) 0.0176(4) Uani 1 1 d . . . . .
H10 H 0.241108 0.623770 0.811568 0.021 Uiso 1 1 calc R U . . .
C11 C 0.17261(12) 0.7357(2) 0.94013(7) 0.0147(3) Uani 1 1 d . . . . .
C12 C 0.28888(12) 1.1135(2) 1.02302(7) 0.0135(3) Uani 1 1 d . . . . .
C13 C 0.37453(13) 1.0034(2) 1.04597(7) 0.0151(3) Uani 1 1 d D . . . .
H13 H 0.364503 0.875833 1.043939 0.018 Uiso 0.09 1 calc R U P A 2
C14 C 0.47341(13) 1.0692(2) 1.07158(7) 0.0185(4) Uani 1 1 d . . . . .
H14 H 0.529521 0.988732 1.087281 0.022 Uiso 1 1 calc R U . . .
C15 C 0.48922(14) 1.2547(2) 1.07393(8) 0.0220(4) Uani 1 1 d . . . . .
H15 H 0.556896 1.302955 1.091223 0.026 Uiso 1 1 calc R U . . .
C16 C 0.40633(14) 1.3704(2) 1.05107(8) 0.0209(4) Uani 1 1 d . . . . .
H16 H 0.417409 1.497841 1.052258 0.025 Uiso 1 1 calc R U . . .
C17 C 0.30708(14) 1.2993(2) 1.02643(7) 0.0175(4) Uani 1 1 d D U . . .
H17 H 0.250258 1.379622 1.011544 0.021 Uiso 0.91 1 calc R U P B 1
C18 C 0.02809(14) 0.5961(2) 1.19920(8) 0.0201(4) Uani 1 1 d . . . . .
H18A H -0.051710 0.610502 1.189920 0.030 Uiso 1 1 calc R U . . .
H18B H 0.047684 0.467442 1.197078 0.030 Uiso 1 1 calc R U . . .
H18C H 0.047612 0.642101 1.240542 0.030 Uiso 1 1 calc R U . . .
C19 C 0.21641(13) 0.6797(2) 1.16709(8) 0.0197(4) Uani 1 1 d . . . . .
H19A H 0.257274 0.747748 1.137193 0.029 Uiso 1 1 calc R U . . .
H19B H 0.235822 0.725650 1.208448 0.029 Uiso 1 1 calc R U . . .
H19C H 0.235895 0.550990 1.164985 0.029 Uiso 1 1 calc R U . . .
C20 C 0.31450(13) 1.2431(2) 0.82974(7) 0.0158(3) Uani 1 1 d . . . . .
C21 C 0.41050(14) 1.3411(2) 0.84476(8) 0.0201(4) Uani 1 1 d . . . . .
H21 H 0.437866 1.350036 0.886347 0.024 Uiso 1 1 calc R U . . .
C22 C 0.46628(15) 1.4259(2) 0.79902(8) 0.0246(4) Uani 1 1 d . . . . .
H22 H 0.531926 1.492693 0.809331 0.029 Uiso 1 1 calc R U . . .
C23 C 0.42674(15) 1.4135(2) 0.73866(8) 0.0255(4) Uani 1 1 d . . . . .
H23 H 0.464934 1.471888 0.707374 0.031 Uiso 1 1 calc R U . . .
C24 C 0.33099(15) 1.3157(2) 0.72373(8) 0.0232(4) Uani 1 1 d . . . . .
H24 H 0.303969 1.306848 0.682075 0.028 Uiso 1 1 calc R U . . .
C25 C 0.27434(14) 1.2305(2) 0.76908(8) 0.0189(4) Uani 1 1 d . . . . .
H25 H 0.208586 1.164094 0.758659 0.023 Uiso 1 1 calc R U . . .
N1 N 0.19024(11) 0.62126(18) 0.89432(6) 0.0177(3) Uani 1 1 d . . . . .
N2 N 0.25108(11) 0.87590(18) 0.83731(6) 0.0169(3) Uani 1 1 d . . . . .
N3 N 0.25713(11) 1.16485(18) 0.87887(6) 0.0166(3) Uani 1 1 d D . . . .
O1 O 0.09987(10) 1.18233(15) 1.10544(6) 0.0242(3) Uani 1 1 d . . . . .
O2 O 0.13124(9) 0.64709(14) 0.98921(5) 0.0167(3) Uani 1 1 d . . . . .
F1 F 0.36130(8) 0.82086(12) 1.04220(4) 0.0181(2) Uani 0.95 1 d D . P C 1
F2 F 0.2445(12) 1.4218(18) 0.9935(7) 0.0201(12) Uani 0.05 1 d D U P D 2
H3 H 0.2548(16) 1.233(2) 0.9118(5) 0.028(5) Uiso 1 1 d 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 C2 1.493(2) . ?
C1 C6 1.339(2) . ?
C1 O2 1.3741(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.536(2) . ?
C3 C4 1.535(2) . ?
C3 C18 1.531(2) . ?
C3 C19 1.533(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.515(2) . ?
C5 C6 1.467(2) . ?
C5 O1 1.2238(19) . ?
C6 C7 1.515(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.515(2) . ?
C7 C12 1.529(2) . ?
C8 C9 1.414(2) . ?
C8 C11 1.377(2) . ?
C9 N2 1.344(2) . ?
C9 N3 1.367(2) . ?
C10 H10 0.9500 . ?
C10 N1 1.329(2) . ?
C10 N2 1.332(2) . ?
C11 N1 1.336(2) . ?
C11 O2 1.3744(19) . ?
C12 C13 1.386(2) . ?
C12 C17 1.390(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.378(2) . ?
C13 F1 1.3585(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.389(2) . ?
C17 H17 0.9500 . ?
C17 F2 1.358(2) . ?
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 C21 1.391(2) . ?
C20 C25 1.386(2) . ?
C20 N3 1.433(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.378(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.387(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.387(2) . ?
C25 H25 0.9500 . ?
N3 H3 0.8800(11) . ?

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
C6 C1 C2 125.16(14) . . ?
C6 C1 O2 123.45(14) . . ?
O2 C1 C2 111.39(13) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 C3 110.91(13) . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C4 C3 C2 108.00(13) . . ?
C18 C3 C2 108.93(13) . . ?
C18 C3 C4 109.61(13) . . ?
C18 C3 C19 109.32(13) . . ?
C19 C3 C2 109.96(13) . . ?
C19 C3 C4 110.98(13) . . ?
C3 C4 H4A 108.4 . . ?
C3 C4 H4B 108.4 . . ?
H4A C4 H4B 107.5 . . ?
C5 C4 C3 115.32(13) . . ?
C5 C4 H4A 108.4 . . ?
C5 C4 H4B 108.4 . . ?
C6 C5 C4 118.58(14) . . ?
O1 C5 C4 120.82(15) . . ?
O1 C5 C6 120.61(15) . . ?
C1 C6 C5 118.65(14) . . ?
C1 C6 C7 123.04(14) . . ?
C5 C6 C7 118.21(13) . . ?
C6 C7 H7 108.2 . . ?
C6 C7 C12 110.29(13) . . ?
C8 C7 C6 109.55(13) . . ?
C8 C7 H7 108.2 . . ?
C8 C7 C12 112.27(12) . . ?
C12 C7 H7 108.2 . . ?
C9 C8 C7 123.98(14) . . ?
C11 C8 C7 122.10(14) . . ?
C11 C8 C9 113.86(14) . . ?
N2 C9 C8 122.43(14) . . ?
N2 C9 N3 117.40(14) . . ?
N3 C9 C8 120.17(14) . . ?
N1 C10 H10 115.9 . . ?
N1 C10 N2 128.15(15) . . ?
N2 C10 H10 115.9 . . ?
N1 C11 C8 126.04(15) . . ?
N1 C11 O2 111.36(13) . . ?
O2 C11 C8 122.60(14) . . ?
C13 C12 C7 121.98(14) . . ?
C13 C12 C17 116.48(15) . . ?
C17 C12 C7 121.52(14) . . ?
C12 C13 H13 118.2 . . ?
C14 C13 C12 123.53(15) . . ?
C14 C13 H13 118.2 . . ?
F1 C13 C12 118.44(14) . . ?
F1 C13 C14 118.02(14) . . ?
C13 C14 H14 120.7 . . ?
C13 C14 C15 118.57(15) . . ?
C15 C14 H14 120.7 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.04(16) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.78(16) . . ?
C17 C16 H16 120.1 . . ?
C12 C17 H17 119.2 . . ?
C16 C17 C12 121.59(16) . . ?
C16 C17 H17 119.2 . . ?
F2 C17 C12 123.1(8) . . ?
F2 C17 C16 113.3(8) . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C3 C19 H19A 109.5 . . ?
C3 C19 H19B 109.5 . . ?
C3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 N3 117.88(15) . . ?
C25 C20 C21 120.03(15) . . ?
C25 C20 N3 122.02(15) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 119.99(16) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.17(17) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 120.1 . . ?
C22 C23 C24 119.80(16) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.57(17) . . ?
C25 C24 H24 119.7 . . ?
C20 C25 C24 119.44(16) . . ?
C20 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C10 N1 C11 113.69(14) . . ?
C10 N2 C9 115.80(14) . . ?
C9 N3 C20 125.37(13) . . ?
C9 N3 H3 117.3(12) . . ?
C20 N3 H3 114.9(12) . . ?
C1 O2 C11 118.64(12) . . ?

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
C1 C2 C3 C4 52.59(16) . . . . ?
C1 C2 C3 C18 171.57(13) . . . . ?
C1 C2 C3 C19 -68.64(16) . . . . ?
C1 C6 C7 C8 8.3(2) . . . . ?
C1 C6 C7 C12 -115.79(16) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
C2 C1 C6 C7 175.66(14) . . . . ?
C2 C1 O2 C11 178.49(13) . . . . ?
C2 C3 C4 C5 -48.64(18) . . . . ?
C3 C4 C5 C6 19.7(2) . . . . ?
C3 C4 C5 O1 -160.38(15) . . . . ?
C4 C5 C6 C1 6.8(2) . . . . ?
C4 C5 C6 C7 -169.73(13) . . . . ?
C5 C6 C7 C8 -175.40(13) . . . . ?
C5 C6 C7 C12 60.54(17) . . . . ?
C6 C1 C2 C3 -30.8(2) . . . . ?
C6 C1 O2 C11 -2.2(2) . . . . ?
C6 C7 C8 C9 174.78(14) . . . . ?
C6 C7 C8 C11 -8.4(2) . . . . ?
C6 C7 C12 C13 59.73(19) . . . . ?
C6 C7 C12 C17 -118.85(16) . . . . ?
C7 C8 C9 N2 176.53(14) . . . . ?
C7 C8 C9 N3 -3.6(2) . . . . ?
C7 C8 C11 N1 -175.14(15) . . . . ?
C7 C8 C11 O2 3.9(2) . . . . ?
C7 C12 C13 C14 -178.18(14) . . . . ?
C7 C12 C13 F1 2.9(2) . . . . ?
C7 C12 C17 C16 179.20(15) . . . . ?
C7 C12 C17 F2 -17.8(9) . . . . ?
C8 C7 C12 C13 -62.75(19) . . . . ?
C8 C7 C12 C17 118.67(16) . . . . ?
C8 C9 N2 C10 -0.6(2) . . . . ?
C8 C9 N3 C20 169.48(14) . . . . ?
C8 C11 N1 C10 -2.1(2) . . . . ?
C8 C11 O2 C1 2.0(2) . . . . ?
C9 C8 C11 N1 2.0(2) . . . . ?
C9 C8 C11 O2 -178.96(13) . . . . ?
C11 C8 C9 N2 -0.6(2) . . . . ?
C11 C8 C9 N3 179.30(14) . . . . ?
C12 C7 C8 C9 -62.32(19) . . . . ?
C12 C7 C8 C11 114.53(16) . . . . ?
C12 C13 C14 C15 -0.9(2) . . . . ?
C13 C12 C17 C16 0.6(2) . . . . ?
C13 C12 C17 F2 163.6(9) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
C14 C15 C16 C17 0.7(2) . . . . ?
C15 C16 C17 C12 -1.1(2) . . . . ?
C15 C16 C17 F2 -165.7(8) . . . . ?
C17 C12 C13 C14 0.5(2) . . . . ?
C17 C12 C13 F1 -178.42(13) . . . . ?
C18 C3 C4 C5 -167.19(14) . . . . ?
C19 C3 C4 C5 71.97(18) . . . . ?
C20 C21 C22 C23 0.1(3) . . . . ?
C21 C20 C25 C24 0.3(2) . . . . ?
C21 C20 N3 C9 -122.23(18) . . . . ?
C21 C22 C23 C24 -0.1(3) . . . . ?
C22 C23 C24 C25 0.2(3) . . . . ?
C23 C24 C25 C20 -0.3(3) . . . . ?
C25 C20 C21 C22 -0.2(2) . . . . ?
C25 C20 N3 C9 60.8(2) . . . . ?
N1 C10 N2 C9 0.6(2) . . . . ?
N1 C11 O2 C1 -178.84(13) . . . . ?
N2 C9 N3 C20 -10.7(2) . . . . ?
N2 C10 N1 C11 0.7(2) . . . . ?
N3 C9 N2 C10 179.55(14) . . . . ?
N3 C20 C21 C22 -177.24(15) . . . . ?
N3 C20 C25 C24 177.22(15) . . . . ?
O1 C5 C6 C1 -173.18(15) . . . . ?
O1 C5 C6 C7 10.3(2) . . . . ?
O2 C1 C2 C3 148.48(13) . . . . ?
O2 C1 C6 C5 -179.85(14) . . . . ?
O2 C1 C6 C7 -3.5(2) . . . . ?
O2 C11 N1 C10 178.82(13) . . . . ?
F1 C13 C14 C15 178.01(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_3h
_database_code_depnum_ccdc_archive 'CCDC 2219312'
loop_
_audit_author_name
_audit_author_address
'Sizwe Zamisa'
;University of KwaZulu Natal
South Africa
;
_audit_update_record             
;
2023-04-12 deposited with the CCDC.	2023-07-12 downloaded from the CCDC.
;
_audit_creation_date             2023-04-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H21 F N4 O4'
_chemical_formula_sum            'C25 H21 F N4 O4'
_chemical_formula_weight         460.46
_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/c 1'
_space_group_name_Hall           '-I 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   21.5323(4)
_cell_length_b                   6.93030(10)
_cell_length_c                   29.2911(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.5550(10)
_cell_angle_gamma                90
_cell_volume                     4362.56(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9225
_cell_measurement_temperature    99.97
_cell_measurement_theta_max      28.41
_cell_measurement_theta_min      4.38
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0630 before and 0.0310 after correction. The Ratio of minimum to maximum transmission is 0.8753. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            17399
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.431
_diffrn_reflns_theta_min         4.265
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4369
_reflns_number_total             5402
_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       'COSMO (Bruker, V1.61, 2009)'
_computing_data_collection       'COSMO (Bruker, V1.61, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         5402
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.017
_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)+(0.0460P)²+3.4918P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0978
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N3-H3
 0.88 with sigma of 0.001
3.a Ternary CH refined with riding coordinates:
 C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B)
3.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C21(H21), C25(H25), C22(H22), C17(H17), C24(H24), C15(H15),
 C16(H16), C14(H14)
3.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;

# start Validation Reply Form
_vrf_PLAT910_3h                  
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         23 Note  
RESPONSE: The reflections at low theta angles that are regarded as
 missing, were fully or in part shaded by the beam stopper.
 Consequently, the F(obs) values were zero or very small though
 F(calc) values were very high. Hence, these reflections were omitted
 from the refinement and this had a negligible impact on the overall
 crystal refinement quality.
;
# end Validation Reply Form

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.48375(3) 0.50616(10) 0.63247(3) 0.02310(17) Uani 1 1 d . . . . .
O2 O 0.36711(4) 0.22167(13) 0.58824(3) 0.01964(18) Uani 1 1 d . . . . .
O1 O 0.51936(4) -0.08151(13) 0.68618(3) 0.02347(19) Uani 1 1 d . . . . .
O4 O 0.80470(4) 0.33796(14) 0.41438(3) 0.0279(2) Uani 1 1 d . . . . .
O3 O 0.73510(4) 0.37633(15) 0.35854(3) 0.0300(2) Uani 1 1 d . . . . .
N3 N 0.56466(5) 0.19009(15) 0.52046(3) 0.0179(2) Uani 1 1 d D . . . .
H3 H 0.5817(6) 0.161(2) 0.5477(2) 0.022 Uiso 1 1 d D U . . .
N2 N 0.47325(5) 0.28667(14) 0.47943(3) 0.0188(2) Uani 1 1 d . . . . .
N4 N 0.75031(5) 0.33921(15) 0.39896(3) 0.0205(2) Uani 1 1 d . . . . .
N1 N 0.37623(5) 0.29678(14) 0.51466(3) 0.0191(2) Uani 1 1 d . . . . .
C9 C 0.50167(5) 0.22518(16) 0.51885(4) 0.0168(2) Uani 1 1 d . . . . .
C6 C 0.44864(5) 0.08155(17) 0.63628(4) 0.0174(2) Uani 1 1 d . . . . .
C7 C 0.49871(5) 0.11639(16) 0.60323(4) 0.0159(2) Uani 1 1 d . . . . .
H7 H 0.517193 -0.011942 0.596350 0.019 Uiso 1 1 calc R U . . .
C12 C 0.55132(5) 0.24296(17) 0.62372(4) 0.0162(2) Uani 1 1 d . . . . .
C11 C 0.40631(5) 0.23690(16) 0.55321(4) 0.0170(2) Uani 1 1 d . . . . .
C10 C 0.41238(6) 0.31777(17) 0.47984(4) 0.0191(2) Uani 1 1 d . . . . .
H10 H 0.392270 0.360158 0.451838 0.023 Uiso 1 1 calc R U . . .
C8 C 0.46898(5) 0.19452(16) 0.55863(4) 0.0159(2) Uani 1 1 d . . . . .
C1 C 0.38961(5) 0.13777(17) 0.62832(4) 0.0181(2) Uani 1 1 d . . . . .
C23 C 0.70182(6) 0.29567(16) 0.42982(4) 0.0184(2) Uani 1 1 d . . . . .
C13 C 0.54260(5) 0.43365(17) 0.63628(4) 0.0179(2) Uani 1 1 d . . . . .
C5 C 0.46571(6) -0.02865(17) 0.67805(4) 0.0192(2) Uani 1 1 d . . . . .
C21 C 0.59337(6) 0.27511(17) 0.44253(4) 0.0183(2) Uani 1 1 d . . . . .
H21 H 0.551032 0.284746 0.431553 0.022 Uiso 1 1 calc R U . . .
C20 C 0.60863(5) 0.22404(16) 0.48808(4) 0.0165(2) Uani 1 1 d . . . . .
C25 C 0.67143(6) 0.20518(17) 0.50345(4) 0.0199(2) Uani 1 1 d . . . . .
H25 H 0.681689 0.166853 0.534133 0.024 Uiso 1 1 calc R U . . .
C22 C 0.64033(6) 0.31138(16) 0.41366(4) 0.0184(2) Uani 1 1 d . . . . .
H22 H 0.630402 0.347054 0.382748 0.022 Uiso 1 1 calc R U . . .
C17 C 0.61199(5) 0.17203(18) 0.62966(4) 0.0201(2) Uani 1 1 d . . . . .
H17 H 0.619866 0.040930 0.622513 0.024 Uiso 1 1 calc R U . . .
C24 C 0.71847(6) 0.24145(17) 0.47468(4) 0.0201(2) Uani 1 1 d . . . . .
H24 H 0.760943 0.229758 0.485173 0.024 Uiso 1 1 calc R U . . .
C15 C 0.65020(6) 0.47977(19) 0.65676(4) 0.0236(3) Uani 1 1 d . . . . .
H15 H 0.683859 0.560170 0.667253 0.028 Uiso 1 1 calc R U . . .
C16 C 0.66101(6) 0.2882(2) 0.64574(4) 0.0234(3) Uani 1 1 d . . . . .
H16 H 0.701938 0.236870 0.649216 0.028 Uiso 1 1 calc R U . . .
C14 C 0.59023(6) 0.55361(18) 0.65244(4) 0.0219(2) Uani 1 1 d . . . . .
H14 H 0.582127 0.683668 0.660414 0.026 Uiso 1 1 calc R U . . .
C2 C 0.33910(6) 0.11619(19) 0.66074(4) 0.0216(2) Uani 1 1 d . . . . .
H2A H 0.311168 0.009817 0.650032 0.026 Uiso 1 1 calc R U . . .
H2B H 0.314188 0.236310 0.660415 0.026 Uiso 1 1 calc R U . . .
C4 C 0.41434(6) -0.08165(19) 0.70853(4) 0.0227(3) Uani 1 1 d . . . . .
H4A H 0.432597 -0.104279 0.739925 0.027 Uiso 1 1 calc R U . . .
H4B H 0.394884 -0.203749 0.697439 0.027 Uiso 1 1 calc R U . . .
C3 C 0.36385(6) 0.0740(2) 0.71010(4) 0.0235(3) Uani 1 1 d . . . . .
C18 C 0.31067(6) -0.0011(2) 0.73755(5) 0.0316(3) Uani 1 1 d . . . . .
H18A H 0.277363 0.095321 0.737218 0.047 Uiso 1 1 calc R U . . .
H18B H 0.326171 -0.025556 0.769187 0.047 Uiso 1 1 calc R U . . .
H18C H 0.294422 -0.121324 0.723819 0.047 Uiso 1 1 calc R U . . .
C19 C 0.39105(7) 0.2579(2) 0.73255(5) 0.0305(3) Uani 1 1 d . . . . .
H19A H 0.424098 0.308249 0.714316 0.046 Uiso 1 1 calc R U . . .
H19B H 0.408278 0.227970 0.763490 0.046 Uiso 1 1 calc R U . . .
H19C H 0.358167 0.354957 0.734177 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 C13 1.3613(13) . ?
O2 C11 1.3726(14) . ?
O2 C1 1.3714(14) . ?
O1 C5 1.2213(15) . ?
O4 N4 1.2289(13) . ?
O3 N4 1.2357(13) . ?
N3 H3 0.8799(10) . ?
N3 C9 1.3759(15) . ?
N3 C20 1.4009(15) . ?
N2 C9 1.3424(15) . ?
N2 C10 1.3291(15) . ?
N4 C23 1.4543(15) . ?
N1 C11 1.3326(15) . ?
N1 C10 1.3287(16) . ?
C9 C8 1.4141(16) . ?
C6 C7 1.5124(16) . ?
C6 C1 1.3359(16) . ?
C6 C5 1.4694(16) . ?
C7 H7 1.0000 . ?
C7 C12 1.5259(15) . ?
C7 C8 1.5187(15) . ?
C12 C13 1.3877(16) . ?
C12 C17 1.3966(16) . ?
C11 C8 1.3804(16) . ?
C10 H10 0.9500 . ?
C1 C2 1.4951(16) . ?
C23 C22 1.3825(17) . ?
C23 C24 1.3921(16) . ?
C13 C14 1.3809(17) . ?
C5 C4 1.5092(17) . ?
C21 H21 0.9500 . ?
C21 C20 1.3997(16) . ?
C21 C22 1.3808(16) . ?
C20 C25 1.4046(16) . ?
C25 H25 0.9500 . ?
C25 C24 1.3805(16) . ?
C22 H22 0.9500 . ?
C17 H17 0.9500 . ?
C17 C16 1.3866(17) . ?
C24 H24 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.3894(19) . ?
C15 C14 1.3874(18) . ?
C16 H16 0.9500 . ?
C14 H14 0.9500 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5376(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.5345(18) . ?
C3 C18 1.5307(18) . ?
C3 C19 1.5333(19) . ?
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
C1 O2 C11 118.14(9) . . ?
C9 N3 H3 115.2(9) . . ?
C9 N3 C20 130.79(10) . . ?
C20 N3 H3 113.0(9) . . ?
C10 N2 C9 116.16(10) . . ?
O4 N4 O3 122.92(10) . . ?
O4 N4 C23 118.33(10) . . ?
O3 N4 C23 118.74(10) . . ?
C10 N1 C11 114.04(10) . . ?
N3 C9 C8 119.03(10) . . ?
N2 C9 N3 118.77(10) . . ?
N2 C9 C8 122.19(11) . . ?
C1 C6 C7 123.36(10) . . ?
C1 C6 C5 118.88(11) . . ?
C5 C6 C7 117.68(10) . . ?
C6 C7 H7 107.2 . . ?
C6 C7 C12 112.41(9) . . ?
C6 C7 C8 109.17(9) . . ?
C12 C7 H7 107.2 . . ?
C8 C7 H7 107.2 . . ?
C8 C7 C12 113.36(9) . . ?
C13 C12 C7 122.85(10) . . ?
C13 C12 C17 116.29(11) . . ?
C17 C12 C7 120.83(10) . . ?
O2 C11 C8 122.66(10) . . ?
N1 C11 O2 111.61(10) . . ?
N1 C11 C8 125.72(11) . . ?
N2 C10 H10 116.1 . . ?
N1 C10 N2 127.89(11) . . ?
N1 C10 H10 116.1 . . ?
C9 C8 C7 123.88(10) . . ?
C11 C8 C9 113.97(10) . . ?
C11 C8 C7 122.12(10) . . ?
O2 C1 C2 110.72(10) . . ?
C6 C1 O2 123.70(10) . . ?
C6 C1 C2 125.57(11) . . ?
C22 C23 N4 118.69(10) . . ?
C22 C23 C24 121.97(11) . . ?
C24 C23 N4 119.33(11) . . ?
F1 C13 C12 118.06(10) . . ?
F1 C13 C14 118.27(11) . . ?
C14 C13 C12 123.67(11) . . ?
O1 C5 C6 120.20(11) . . ?
O1 C5 C4 122.06(11) . . ?
C6 C5 C4 117.67(10) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C22 C21 C20 119.49(11) . . ?
N3 C20 C25 116.42(10) . . ?
C21 C20 N3 124.01(10) . . ?
C21 C20 C25 119.57(11) . . ?
C20 C25 H25 119.5 . . ?
C24 C25 C20 121.05(11) . . ?
C24 C25 H25 119.5 . . ?
C23 C22 H22 120.1 . . ?
C21 C22 C23 119.88(11) . . ?
C21 C22 H22 120.1 . . ?
C12 C17 H17 119.2 . . ?
C16 C17 C12 121.63(12) . . ?
C16 C17 H17 119.2 . . ?
C23 C24 H24 121.0 . . ?
C25 C24 C23 118.01(11) . . ?
C25 C24 H24 121.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 119.97(12) . . ?
C17 C16 C15 119.92(12) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C13 C14 C15 118.46(12) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C1 C2 C3 113.13(10) . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C5 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C5 C4 C3 113.16(10) . . ?
H4A C4 H4B 107.8 . . ?
C3 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C4 C3 C2 108.07(10) . . ?
C18 C3 C2 109.36(10) . . ?
C18 C3 C4 109.33(11) . . ?
C18 C3 C19 109.64(11) . . ?
C19 C3 C2 110.26(11) . . ?
C19 C3 C4 110.16(11) . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C3 C19 H19A 109.5 . . ?
C3 C19 H19B 109.5 . . ?
C3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C21 H21 F1 0.95 2.45 3.0707(14) 122.8 5_666 yes
C21 H21 N2 0.95 2.25 2.8655(16) 121.7 . yes
C17 H17 O4 0.95 2.45 3.2449(15) 141.1 4_645 yes
C14 H14 O1 0.95 2.27 3.1443(16) 152.0 1_565 yes

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
F1 C13 C14 C15 179.43(11) . . . . ?
O2 C11 C8 C9 -178.10(10) . . . . ?
O2 C11 C8 C7 3.62(17) . . . . ?
O2 C1 C2 C3 -164.80(10) . . . . ?
O1 C5 C4 C3 147.86(12) . . . . ?
O4 N4 C23 C22 175.04(11) . . . . ?
O4 N4 C23 C24 -4.34(16) . . . . ?
O3 N4 C23 C22 -4.74(16) . . . . ?
O3 N4 C23 C24 175.88(11) . . . . ?
N3 C9 C8 C7 -2.62(17) . . . . ?
N3 C9 C8 C11 179.14(10) . . . . ?
N3 C20 C25 C24 -177.93(11) . . . . ?
N2 C9 C8 C7 177.07(10) . . . . ?
N2 C9 C8 C11 -1.17(16) . . . . ?
N4 C23 C22 C21 -178.54(10) . . . . ?
N4 C23 C24 C25 178.59(11) . . . . ?
N1 C11 C8 C9 1.73(17) . . . . ?
N1 C11 C8 C7 -176.54(11) . . . . ?
C9 N3 C20 C21 -11.36(19) . . . . ?
C9 N3 C20 C25 168.38(11) . . . . ?
C9 N2 C10 N1 0.55(18) . . . . ?
C6 C7 C12 C13 -64.20(14) . . . . ?
C6 C7 C12 C17 117.54(12) . . . . ?
C6 C7 C8 C9 -173.65(10) . . . . ?
C6 C7 C8 C11 4.45(15) . . . . ?
C6 C1 C2 C3 16.13(18) . . . . ?
C6 C5 C4 C3 -35.35(15) . . . . ?
C7 C6 C1 O2 4.38(18) . . . . ?
C7 C6 C1 C2 -176.67(11) . . . . ?
C7 C6 C5 O1 3.21(16) . . . . ?
C7 C6 C5 C4 -173.64(10) . . . . ?
C7 C12 C13 F1 3.88(16) . . . . ?
C7 C12 C13 C14 -176.20(11) . . . . ?
C7 C12 C17 C16 176.21(11) . . . . ?
C12 C7 C8 C9 60.20(14) . . . . ?
C12 C7 C8 C11 -121.70(11) . . . . ?
C12 C13 C14 C15 -0.50(18) . . . . ?
C12 C17 C16 C15 0.60(18) . . . . ?
C11 O2 C1 C6 4.57(16) . . . . ?
C11 O2 C1 C2 -174.52(10) . . . . ?
C11 N1 C10 N2 -0.09(18) . . . . ?
C10 N2 C9 N3 179.84(10) . . . . ?
C10 N2 C9 C8 0.15(16) . . . . ?
C10 N1 C11 O2 178.70(9) . . . . ?
C10 N1 C11 C8 -1.15(17) . . . . ?
C8 C7 C12 C13 60.21(14) . . . . ?
C8 C7 C12 C17 -118.05(12) . . . . ?
C1 O2 C11 N1 171.61(10) . . . . ?
C1 O2 C11 C8 -8.53(16) . . . . ?
C1 C6 C7 C12 118.32(12) . . . . ?
C1 C6 C7 C8 -8.36(15) . . . . ?
C1 C6 C5 O1 -179.88(11) . . . . ?
C1 C6 C5 C4 3.26(16) . . . . ?
C1 C2 C3 C4 -45.26(14) . . . . ?
C1 C2 C3 C18 -164.19(11) . . . . ?
C1 C2 C3 C19 75.19(13) . . . . ?
C13 C12 C17 C16 -2.16(17) . . . . ?
C5 C6 C7 C12 -64.92(13) . . . . ?
C5 C6 C7 C8 168.39(9) . . . . ?
C5 C6 C1 O2 -172.34(10) . . . . ?
C5 C6 C1 C2 6.62(18) . . . . ?
C5 C4 C3 C2 55.07(13) . . . . ?
C5 C4 C3 C18 174.02(10) . . . . ?
C5 C4 C3 C19 -65.44(13) . . . . ?
C21 C20 C25 C24 1.82(18) . . . . ?
C20 N3 C9 N2 6.73(18) . . . . ?
C20 N3 C9 C8 -173.57(11) . . . . ?
C20 C21 C22 C23 0.47(17) . . . . ?
C20 C25 C24 C23 -0.56(18) . . . . ?
C22 C23 C24 C25 -0.78(18) . . . . ?
C22 C21 C20 N3 177.98(11) . . . . ?
C22 C21 C20 C25 -1.76(17) . . . . ?
C17 C12 C13 F1 -177.79(10) . . . . ?
C17 C12 C13 C14 2.14(17) . . . . ?
C24 C23 C22 C21 0.83(18) . . . . ?
C16 C15 C14 C13 -1.20(18) . . . . ?
C14 C15 C16 C17 1.14(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_3b
_database_code_depnum_ccdc_archive 'CCDC 2219309'
loop_
_audit_author_name
_audit_author_address
'Sizwe Zamisa'
;University of KwaZulu Natal
South Africa
;
_audit_update_record             
;
2023-04-12 deposited with the CCDC.	2023-07-12 downloaded from the CCDC.
;
_audit_creation_date             2023-04-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H24 F N3 O2'
_chemical_formula_sum            'C26 H24 F N3 O2'
_chemical_formula_weight         429.48
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.1596(4)
_cell_length_b                   7.4148(3)
_cell_length_c                   23.0902(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.662(2)
_cell_angle_gamma                90
_cell_volume                     2067.78(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3416
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.46
_cell_measurement_theta_min      2.59
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13147
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.547
_diffrn_reflns_theta_min         1.776
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3118
_reflns_number_total             4230
_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-plus (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4230
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0423
_refine_ls_restrained_S_all      1.009
_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)+(0.0416P)²+0.9652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.1021
_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. Restrained distances
 N3-H3
 0.88 with sigma of 0.001
3. Rigid bond restraints
 C15, F1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4.a Ternary CH refined with riding coordinates:
 C7(H7)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B)
4.c Me refined with riding coordinates:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
4.d Aromatic/amide H refined with riding coordinates:
 C10(H10), C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22),
 C24(H24), C25(H25)
4.e Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.61035(13) 0.7550(2) 1.05004(7) 0.0144(4) Uani 1 1 d . . . . .
C2 C 0.57023(14) 0.8723(2) 1.09559(7) 0.0178(4) Uani 1 1 d . . . . .
H2A H 0.488683 0.883463 1.088172 0.021 Uiso 1 1 calc R U . . .
H2B H 0.602371 0.994377 1.093147 0.021 Uiso 1 1 calc R U . . .
C3 C 0.60201(13) 0.7962(2) 1.15723(7) 0.0170(4) Uani 1 1 d . . . . .
C4 C 0.56813(14) 0.5971(2) 1.15712(7) 0.0182(4) Uani 1 1 d . . . . .
H4A H 0.598740 0.542849 1.194742 0.022 Uiso 1 1 calc R U . . .
H4B H 0.486414 0.590408 1.154773 0.022 Uiso 1 1 calc R U . . .
C5 C 0.60537(13) 0.4848(2) 1.10818(7) 0.0157(4) Uani 1 1 d . . . . .
C6 C 0.62839(13) 0.5772(2) 1.05449(7) 0.0140(4) Uani 1 1 d . . . . .
C7 C 0.67530(13) 0.4671(2) 1.00789(7) 0.0137(4) Uani 1 1 d . . . . .
H7 H 0.623725 0.364340 0.997027 0.016 Uiso 1 1 calc R U . . .
C8 C 0.68072(13) 0.5831(2) 0.95412(7) 0.0145(4) Uani 1 1 d . . . . .
C9 C 0.71315(13) 0.5176(2) 0.90100(7) 0.0143(4) Uani 1 1 d . . . . .
C10 C 0.70224(14) 0.8001(2) 0.86298(7) 0.0176(4) Uani 1 1 d . . . . .
H10 H 0.709982 0.876819 0.830760 0.021 Uiso 1 1 calc R U . . .
C11 C 0.66089(13) 0.7657(2) 0.95400(7) 0.0144(4) Uani 1 1 d . . . . .
C12 C 0.72732(14) 0.8155(3) 1.17461(8) 0.0240(4) Uani 1 1 d . . . . .
H12A H 0.767205 0.747560 1.147223 0.036 Uiso 1 1 calc R U . . .
H12B H 0.748017 0.943135 1.173592 0.036 Uiso 1 1 calc R U . . .
H12C H 0.746666 0.768240 1.214115 0.036 Uiso 1 1 calc R U . . .
C13 C 0.53989(15) 0.9025(3) 1.20007(7) 0.0219(4) Uani 1 1 d . . . . .
H13A H 0.562132 1.029473 1.199803 0.033 Uiso 1 1 calc R U . . .
H13B H 0.459995 0.892909 1.188431 0.033 Uiso 1 1 calc R U . . .
H13C H 0.557765 0.853059 1.239400 0.033 Uiso 1 1 calc R U . . .
C14 C 0.78872(13) 0.3894(2) 1.02981(7) 0.0131(4) Uani 1 1 d . . . . .
C15 C 0.87881(13) 0.4991(2) 1.04743(7) 0.0143(3) Uani 1 1 d . U . . .
C16 C 0.98339(14) 0.4332(2) 1.06559(7) 0.0173(4) Uani 1 1 d . . . . .
H16 H 1.042741 0.513068 1.077660 0.021 Uiso 1 1 calc R U . . .
C17 C 0.99996(14) 0.2490(3) 1.06586(7) 0.0197(4) Uani 1 1 d . . . . .
H17 H 1.071543 0.201022 1.077569 0.024 Uiso 1 1 calc R U . . .
C18 C 0.91228(14) 0.1341(2) 1.04907(7) 0.0194(4) Uani 1 1 d . . . . .
H18 H 0.923568 0.007269 1.049360 0.023 Uiso 1 1 calc R U . . .
C19 C 0.80776(14) 0.2045(2) 1.03179(7) 0.0161(4) Uani 1 1 d . . . . .
H19 H 0.747860 0.124455 1.021068 0.019 Uiso 1 1 calc R U . . .
C20 C 0.78829(13) 0.2617(2) 0.84843(7) 0.0149(4) Uani 1 1 d . . . . .
C21 C 0.88146(13) 0.1559(2) 0.86223(7) 0.0166(4) Uani 1 1 d . . . . .
H21 H 0.909431 0.137286 0.901931 0.020 Uiso 1 1 calc R U . . .
C22 C 0.93422(14) 0.0769(2) 0.81860(7) 0.0195(4) Uani 1 1 d . . . . .
H22 H 0.997687 0.003789 0.828711 0.023 Uiso 1 1 calc R U . . .
C23 C 0.89536(15) 0.1035(2) 0.76011(7) 0.0196(4) Uani 1 1 d . . . . .
C24 C 0.80055(15) 0.2073(2) 0.74694(7) 0.0199(4) Uani 1 1 d . . . . .
H24 H 0.771848 0.224472 0.707284 0.024 Uiso 1 1 calc R U . . .
C25 C 0.74686(14) 0.2862(2) 0.79026(7) 0.0181(4) Uani 1 1 d . . . . .
H25 H 0.682174 0.356648 0.780275 0.022 Uiso 1 1 calc R U . . .
C26 C 0.95672(17) 0.0286(3) 0.71233(8) 0.0309(5) Uani 1 1 d . . . . .
H26A H 0.913796 0.051023 0.674424 0.046 Uiso 1 1 calc R U . . .
H26B H 0.967155 -0.101583 0.717972 0.046 Uiso 1 1 calc R U . . .
H26C H 1.029088 0.087504 0.713557 0.046 Uiso 1 1 calc R U . . .
N1 N 0.67181(11) 0.8798(2) 0.91045(6) 0.0175(3) Uani 1 1 d . . . . .
N2 N 0.72298(11) 0.6266(2) 0.85535(6) 0.0168(3) Uani 1 1 d . . . . .
N3 N 0.73558(12) 0.3388(2) 0.89472(6) 0.0167(3) Uani 1 1 d D . . . .
O1 O 0.61454(10) 0.32064(17) 1.11263(5) 0.0221(3) Uani 1 1 d . . . . .
O2 O 0.62800(9) 0.85421(16) 1.00153(5) 0.0176(3) Uani 1 1 d . . . . .
F1 F 0.86406(8) 0.68094(13) 1.04649(4) 0.0208(2) Uani 1 1 d . U . . .
H3 H 0.7387(15) 0.2700(19) 0.9259(5) 0.022(5) Uiso 1 1 d 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 C2 1.490(2) . ?
C1 C6 1.338(2) . ?
C1 O2 1.3778(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.538(2) . ?
C3 C4 1.532(3) . ?
C3 C12 1.537(2) . ?
C3 C13 1.531(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.515(2) . ?
C5 C6 1.472(2) . ?
C5 O1 1.226(2) . ?
C6 C7 1.514(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.518(2) . ?
C7 C14 1.526(2) . ?
C8 C9 1.417(2) . ?
C8 C11 1.376(2) . ?
C9 N2 1.345(2) . ?
C9 N3 1.364(2) . ?
C10 H10 0.9500 . ?
C10 N1 1.335(2) . ?
C10 N2 1.326(2) . ?
C11 N1 1.333(2) . ?
C11 O2 1.3772(19) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.387(2) . ?
C14 C19 1.390(2) . ?
C15 C16 1.381(2) . ?
C15 F1 1.360(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.381(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.384(2) . ?
C20 C25 1.391(2) . ?
C20 N3 1.428(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.385(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.392(2) . ?
C23 C24 1.390(3) . ?
C23 C26 1.508(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.386(2) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N3 H3 0.8800(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
C6 C1 C2 125.82(15) . . ?
C6 C1 O2 123.29(15) . . ?
O2 C1 C2 110.89(15) . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C1 C2 C3 111.79(14) . . ?
H2A C2 H2B 107.9 . . ?
C3 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C4 C3 C2 108.26(14) . . ?
C4 C3 C12 110.40(15) . . ?
C12 C3 C2 110.03(14) . . ?
C13 C3 C2 108.62(14) . . ?
C13 C3 C4 110.13(14) . . ?
C13 C3 C12 109.38(14) . . ?
C3 C4 H4A 108.5 . . ?
C3 C4 H4B 108.5 . . ?
H4A C4 H4B 107.5 . . ?
C5 C4 C3 115.29(14) . . ?
C5 C4 H4A 108.5 . . ?
C5 C4 H4B 108.5 . . ?
C6 C5 C4 118.36(16) . . ?
O1 C5 C4 121.05(15) . . ?
O1 C5 C6 120.58(15) . . ?
C1 C6 C5 118.54(15) . . ?
C1 C6 C7 123.27(15) . . ?
C5 C6 C7 118.15(15) . . ?
C6 C7 H7 108.2 . . ?
C6 C7 C8 109.35(14) . . ?
C6 C7 C14 111.62(13) . . ?
C8 C7 H7 108.2 . . ?
C8 C7 C14 111.22(13) . . ?
C14 C7 H7 108.2 . . ?
C9 C8 C7 123.83(15) . . ?
C11 C8 C7 122.36(15) . . ?
C11 C8 C9 113.69(15) . . ?
N2 C9 C8 122.13(16) . . ?
N2 C9 N3 117.61(14) . . ?
N3 C9 C8 120.26(15) . . ?
N1 C10 H10 116.1 . . ?
N2 C10 H10 116.1 . . ?
N2 C10 N1 127.86(16) . . ?
C8 C11 O2 122.31(15) . . ?
N1 C11 C8 126.43(15) . . ?
N1 C11 O2 111.24(15) . . ?
C3 C12 H12A 109.5 . . ?
C3 C12 H12B 109.5 . . ?
C3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C7 121.90(15) . . ?
C15 C14 C19 116.48(15) . . ?
C19 C14 C7 121.60(15) . . ?
C16 C15 C14 123.33(16) . . ?
F1 C15 C14 118.60(14) . . ?
F1 C15 C16 118.07(15) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 C15 118.69(16) . . ?
C17 C16 H16 120.7 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.02(16) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.87(17) . . ?
C19 C18 H18 120.1 . . ?
C14 C19 H19 119.2 . . ?
C18 C19 C14 121.58(16) . . ?
C18 C19 H19 119.2 . . ?
C21 C20 C25 119.45(15) . . ?
C21 C20 N3 118.75(14) . . ?
C25 C20 N3 121.78(15) . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.50(15) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 119.6 . . ?
C21 C22 C23 120.80(16) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 C26 121.09(16) . . ?
C24 C23 C22 118.04(16) . . ?
C24 C23 C26 120.82(16) . . ?
C23 C24 H24 119.2 . . ?
C25 C24 C23 121.61(16) . . ?
C25 C24 H24 119.2 . . ?
C20 C25 H25 120.2 . . ?
C24 C25 C20 119.57(16) . . ?
C24 C25 H25 120.2 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C11 N1 C10 113.55(15) . . ?
C10 N2 C9 116.31(15) . . ?
C9 N3 C20 125.55(14) . . ?
C9 N3 H3 117.8(12) . . ?
C20 N3 H3 113.6(12) . . ?
C11 O2 C1 118.71(14) . . ?

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
C1 C2 C3 C4 -49.73(18) . . . . ?
C1 C2 C3 C12 70.99(18) . . . . ?
C1 C2 C3 C13 -169.30(14) . . . . ?
C1 C6 C7 C8 -8.4(2) . . . . ?
C1 C6 C7 C14 115.05(17) . . . . ?
C2 C1 C6 C5 1.2(2) . . . . ?
C2 C1 C6 C7 -176.49(15) . . . . ?
C2 C1 O2 C11 -177.30(13) . . . . ?
C2 C3 C4 C5 49.50(18) . . . . ?
C3 C4 C5 C6 -23.9(2) . . . . ?
C3 C4 C5 O1 157.26(15) . . . . ?
C4 C5 C6 C1 -3.2(2) . . . . ?
C4 C5 C6 C7 174.65(14) . . . . ?
C5 C6 C7 C8 173.83(13) . . . . ?
C5 C6 C7 C14 -62.68(19) . . . . ?
C6 C1 C2 C3 27.0(2) . . . . ?
C6 C1 O2 C11 3.1(2) . . . . ?
C6 C7 C8 C9 -175.26(14) . . . . ?
C6 C7 C8 C11 8.9(2) . . . . ?
C6 C7 C14 C15 -62.08(19) . . . . ?
C6 C7 C14 C19 119.55(17) . . . . ?
C7 C8 C9 N2 -176.16(14) . . . . ?
C7 C8 C9 N3 3.9(2) . . . . ?
C7 C8 C11 N1 174.63(15) . . . . ?
C7 C8 C11 O2 -4.1(2) . . . . ?
C7 C14 C15 C16 -177.71(14) . . . . ?
C7 C14 C15 F1 1.8(2) . . . . ?
C7 C14 C19 C18 176.83(14) . . . . ?
C8 C7 C14 C15 60.35(19) . . . . ?
C8 C7 C14 C19 -118.02(17) . . . . ?
C8 C9 N2 C10 1.0(2) . . . . ?
C8 C9 N3 C20 -167.55(15) . . . . ?
C8 C11 N1 C10 1.9(2) . . . . ?
C8 C11 O2 C1 -2.5(2) . . . . ?
C9 C8 C11 N1 -1.6(2) . . . . ?
C9 C8 C11 O2 179.66(13) . . . . ?
C11 C8 C9 N2 0.0(2) . . . . ?
C11 C8 C9 N3 -179.98(14) . . . . ?
C12 C3 C4 C5 -70.99(18) . . . . ?
C13 C3 C4 C5 168.12(14) . . . . ?
C14 C7 C8 C9 61.0(2) . . . . ?
C14 C7 C8 C11 -114.79(17) . . . . ?
C14 C15 C16 C17 0.6(2) . . . . ?
C15 C14 C19 C18 -1.6(2) . . . . ?
C15 C16 C17 C18 -1.1(2) . . . . ?
C16 C17 C18 C19 0.2(2) . . . . ?
C17 C18 C19 C14 1.2(2) . . . . ?
C19 C14 C15 C16 0.7(2) . . . . ?
C19 C14 C15 F1 -179.71(13) . . . . ?
C20 C21 C22 C23 0.6(3) . . . . ?
C21 C20 C25 C24 -1.2(3) . . . . ?
C21 C20 N3 C9 125.53(18) . . . . ?
C21 C22 C23 C24 -1.7(3) . . . . ?
C21 C22 C23 C26 175.82(17) . . . . ?
C22 C23 C24 C25 1.5(3) . . . . ?
C23 C24 C25 C20 0.0(3) . . . . ?
C25 C20 C21 C22 0.9(3) . . . . ?
C25 C20 N3 C9 -56.2(2) . . . . ?
C26 C23 C24 C25 -176.09(17) . . . . ?
N1 C10 N2 C9 -0.6(3) . . . . ?
N1 C11 O2 C1 178.54(13) . . . . ?
N2 C9 N3 C20 12.5(2) . . . . ?
N2 C10 N1 C11 -0.8(2) . . . . ?
N3 C9 N2 C10 -179.05(14) . . . . ?
N3 C20 C21 C22 179.26(15) . . . . ?
N3 C20 C25 C24 -179.47(16) . . . . ?
O1 C5 C6 C1 175.68(15) . . . . ?
O1 C5 C6 C7 -6.5(2) . . . . ?
O2 C1 C2 C3 -152.55(13) . . . . ?
O2 C1 C6 C5 -179.29(14) . . . . ?
O2 C1 C6 C7 3.0(2) . . . . ?
O2 C11 N1 C10 -179.17(13) . . . . ?
F1 C15 C16 C17 -178.96(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_3c
_database_code_depnum_ccdc_archive 'CCDC 2219310'
loop_
_audit_author_name
_audit_author_address
'Sizwe Zamisa'
;University of KwaZulu Natal
South Africa
;
_audit_update_record             
;
2023-04-12 deposited with the CCDC.	2023-07-12 downloaded from the CCDC.
;
_audit_creation_date             2023-04-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H21 F2 N3 O2'
_chemical_formula_sum            'C25 H21 F2 N3 O2'
_chemical_formula_weight         433.45
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.1368(3)
_cell_length_b                   7.3737(2)
_cell_length_c                   22.1506(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.5060(10)
_cell_angle_gamma                90
_cell_volume                     1976.20(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9826
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.44
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.374
_exptl_crystal_size_min          0.324
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            32619
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.456
_diffrn_reflns_theta_min         1.683
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4579
_reflns_number_total             4921
_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-plus (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4921
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.042
_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)+(0.0572P)²+1.0093P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1056
_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. Restrained distances
 N3-H3
 0.88 with sigma of 0.001
3.a Ternary CH refined with riding coordinates:
 C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C2(H2A,H2B)
3.c Me refined with riding coordinates:
 C13(H13A,H13B,H13C), C12(H12A,H12B,H12C)
3.d Aromatic/amide H refined with riding coordinates:
 C21(H21), C22(H22), C19(H19), C18(H18), C17(H17), C16(H16), C9(H9), C25(H25),
 C24(H24)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
O1 O 0.10662(7) 0.18365(11) 1.10857(4) 0.01995(17) Uani 1 1 d . . . . .
F1 F 0.36052(5) -0.18073(8) 1.04420(3) 0.01741(15) Uani 1 1 d . . . . .
C13 C 0.21971(9) -0.31812(16) 1.17031(5) 0.0184(2) Uani 1 1 d . . . . .
H13A H 0.260227 -0.250034 1.141168 0.028 Uiso 1 1 calc R U . . .
H13B H 0.239024 -0.271514 1.211209 0.028 Uiso 1 1 calc R U . . .
H13C H 0.239521 -0.446764 1.168613 0.028 Uiso 1 1 calc R U . . .
C3 C 0.09480(8) -0.29625(14) 1.15453(4) 0.01333(19) Uani 1 1 d . . . . .
C11 C 0.06181(8) -0.09534(14) 1.15567(5) 0.0152(2) Uani 1 1 d . . . . .
H11A H -0.019708 -0.087732 1.155067 0.018 Uiso 1 1 calc R U . . .
H11B H 0.092789 -0.041954 1.194354 0.018 Uiso 1 1 calc R U . . .
C4 C 0.09919(8) 0.01875(14) 1.10405(4) 0.01336(19) Uani 1 1 d . . . . .
C5 C 0.12526(8) -0.07373(14) 1.04808(4) 0.01172(19) Uani 1 1 d . . . . .
C6 C 0.17749(8) 0.03642(13) 1.00018(4) 0.01108(18) Uani 1 1 d . . . . .
H6 H 0.127262 0.140202 0.988431 0.013 Uiso 1 1 calc R U . . .
C7 C 0.18831(8) -0.08020(14) 0.94457(4) 0.01178(19) Uani 1 1 d . . . . .
C8 C 0.22591(8) -0.01425(14) 0.88974(4) 0.01244(19) Uani 1 1 d . . . . .
N3 N 0.25021(8) 0.16539(12) 0.88369(4) 0.01449(18) Uani 1 1 d D . . . .
C20 C 0.30482(8) 0.24405(14) 0.83541(4) 0.01275(19) Uani 1 1 d . . . . .
C21 C 0.39797(9) 0.34986(14) 0.85040(5) 0.0159(2) Uani 1 1 d . . . . .
H21 H 0.425321 0.361528 0.891588 0.019 Uiso 1 1 calc R U . . .
C22 C 0.45128(9) 0.43854(16) 0.80563(5) 0.0201(2) Uani 1 1 d . . . . .
H22 H 0.514615 0.511510 0.815610 0.024 Uiso 1 1 calc R U . . .
C23 C 0.40962(10) 0.41760(16) 0.74627(5) 0.0208(2) Uani 1 1 d . . . . .
F2 F 0.46055(7) 0.50437(12) 0.70245(3) 0.0345(2) Uani 1 1 d . . . . .
C12 C 0.03128(9) -0.40237(15) 1.19994(5) 0.0175(2) Uani 1 1 d . . . . .
H12A H 0.052549 -0.530503 1.199079 0.026 Uiso 1 1 calc R U . . .
H12B H 0.048875 -0.353550 1.240703 0.026 Uiso 1 1 calc R U . . .
H12C H -0.048278 -0.391056 1.189112 0.026 Uiso 1 1 calc R U . . .
C2 C 0.06290(8) -0.36991(14) 1.09057(5) 0.0140(2) Uani 1 1 d . . . . .
H2A H 0.092245 -0.494470 1.087203 0.017 Uiso 1 1 calc R U . . .
H2B H -0.018623 -0.375872 1.083818 0.017 Uiso 1 1 calc R U . . .
C1 C 0.10726(8) -0.25306(14) 1.04315(4) 0.01217(19) Uani 1 1 d . . . . .
C14 C 0.28875(8) 0.11352(14) 1.02505(4) 0.01161(19) Uani 1 1 d . . . . .
C19 C 0.30792(8) 0.30006(14) 1.02765(5) 0.0149(2) Uani 1 1 d . . . . .
H19 H 0.250331 0.381056 1.014090 0.018 Uiso 1 1 calc R U . . .
C18 C 0.40988(9) 0.36978(15) 1.04975(5) 0.0186(2) Uani 1 1 d . . . . .
H18 H 0.421862 0.497109 1.050433 0.022 Uiso 1 1 calc R U . . .
C17 C 0.49412(9) 0.25259(16) 1.07082(5) 0.0186(2) Uani 1 1 d . . . . .
H17 H 0.563596 0.299974 1.086088 0.022 Uiso 1 1 calc R U . . .
C16 C 0.47685(8) 0.06696(15) 1.06958(5) 0.0160(2) Uani 1 1 d . . . . .
H16 H 0.533570 -0.014070 1.084344 0.019 Uiso 1 1 calc R U . . .
C15 C 0.37543(8) 0.00202(14) 1.04642(4) 0.01303(19) Uani 1 1 d . . . . .
C10 C 0.16707(8) -0.26412(14) 0.94437(4) 0.01248(19) Uani 1 1 d . . . . .
O2 O 0.12902(6) -0.35243(10) 0.99314(3) 0.01409(16) Uani 1 1 d . . . . .
N1 N 0.18100(7) -0.37833(12) 0.89880(4) 0.01487(18) Uani 1 1 d . . . . .
C9 C 0.21555(8) -0.29807(14) 0.84970(5) 0.0150(2) Uani 1 1 d . . . . .
H9 H 0.225103 -0.375051 0.816118 0.018 Uiso 1 1 calc R U . . .
N2 N 0.23826(7) -0.12332(13) 0.84199(4) 0.01461(18) Uani 1 1 d . . . . .
C25 C 0.26472(9) 0.22499(15) 0.77508(5) 0.0159(2) Uani 1 1 d . . . . .
H25 H 0.201215 0.152665 0.764836 0.019 Uiso 1 1 calc R U . . .
C24 C 0.31802(10) 0.31228(15) 0.72985(5) 0.0192(2) Uani 1 1 d . . . . .
H24 H 0.291897 0.299643 0.688505 0.023 Uiso 1 1 calc R U . . .
H3 H 0.2504(13) 0.2308(18) 0.9169(4) 0.026(4) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.2228(13) . ?
F1 C15 1.3600(12) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 C3 1.5374(14) . ?
C3 C11 1.5353(14) . ?
C3 C12 1.5297(14) . ?
C3 C2 1.5381(14) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C4 1.5174(14) . ?
C4 C5 1.4710(13) . ?
C5 C6 1.5142(13) . ?
C5 C1 1.3433(14) . ?
C6 H6 1.0000 . ?
C6 C7 1.5164(13) . ?
C6 C14 1.5275(13) . ?
C7 C8 1.4166(13) . ?
C7 C10 1.3804(14) . ?
C8 N3 1.3659(13) . ?
C8 N2 1.3463(13) . ?
N3 C20 1.4250(12) . ?
N3 H3 0.8800(10) . ?
C20 C21 1.3921(14) . ?
C20 C25 1.3929(14) . ?
C21 H21 0.9500 . ?
C21 C22 1.3893(15) . ?
C22 H22 0.9500 . ?
C22 C23 1.3799(16) . ?
C23 F2 1.3520(12) . ?
C23 C24 1.3812(16) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.4913(13) . ?
C1 O2 1.3711(12) . ?
C14 C19 1.3955(14) . ?
C14 C15 1.3888(14) . ?
C19 H19 0.9500 . ?
C19 C18 1.3928(15) . ?
C18 H18 0.9500 . ?
C18 C17 1.3910(16) . ?
C17 H17 0.9500 . ?
C17 C16 1.3848(16) . ?
C16 H16 0.9500 . ?
C16 C15 1.3814(14) . ?
C10 O2 1.3720(12) . ?
C10 N1 1.3354(13) . ?
N1 C9 1.3345(13) . ?
C9 H9 0.9500 . ?
C9 N2 1.3315(14) . ?
C25 H25 0.9500 . ?
C25 C24 1.3922(15) . ?
C24 H24 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
C13 C3 C2 110.16(8) . . ?
C11 C3 C13 110.57(9) . . ?
C11 C3 C2 107.99(8) . . ?
C12 C3 C13 109.62(8) . . ?
C12 C3 C11 109.71(8) . . ?
C12 C3 C2 108.76(8) . . ?
C3 C11 H11A 108.4 . . ?
C3 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C4 C11 C3 115.39(8) . . ?
C4 C11 H11A 108.4 . . ?
C4 C11 H11B 108.4 . . ?
O1 C4 C11 120.94(9) . . ?
O1 C4 C5 120.70(9) . . ?
C5 C4 C11 118.35(9) . . ?
C4 C5 C6 118.13(9) . . ?
C1 C5 C4 118.71(9) . . ?
C1 C5 C6 123.06(9) . . ?
C5 C6 H6 108.2 . . ?
C5 C6 C7 109.44(8) . . ?
C5 C6 C14 110.72(8) . . ?
C7 C6 H6 108.2 . . ?
C7 C6 C14 111.93(8) . . ?
C14 C6 H6 108.2 . . ?
C8 C7 C6 123.78(9) . . ?
C10 C7 C6 122.11(9) . . ?
C10 C7 C8 114.03(9) . . ?
N3 C8 C7 120.24(9) . . ?
N2 C8 C7 122.11(9) . . ?
N2 C8 N3 117.65(9) . . ?
C8 N3 C20 125.81(9) . . ?
C8 N3 H3 115.8(10) . . ?
C20 N3 H3 115.7(11) . . ?
C21 C20 N3 117.78(9) . . ?
C21 C20 C25 120.09(9) . . ?
C25 C20 N3 122.05(9) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.57(10) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 120.9 . . ?
C23 C22 C21 118.11(10) . . ?
C23 C22 H22 120.9 . . ?
C22 C23 C24 122.74(10) . . ?
F2 C23 C22 118.51(10) . . ?
F2 C23 C24 118.75(10) . . ?
C3 C12 H12A 109.5 . . ?
C3 C12 H12B 109.5 . . ?
C3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C3 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C1 C2 C3 111.47(8) . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C5 C1 C2 125.24(9) . . ?
C5 C1 O2 123.45(9) . . ?
O2 C1 C2 111.31(8) . . ?
C19 C14 C6 121.44(9) . . ?
C15 C14 C6 121.81(9) . . ?
C15 C14 C19 116.75(9) . . ?
C14 C19 H19 119.4 . . ?
C18 C19 C14 121.27(10) . . ?
C18 C19 H19 119.4 . . ?
C19 C18 H18 120.1 . . ?
C17 C18 C19 119.86(10) . . ?
C17 C18 H18 120.1 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 C18 120.08(10) . . ?
C16 C17 H17 120.0 . . ?
C17 C16 H16 120.7 . . ?
C15 C16 C17 118.63(10) . . ?
C15 C16 H16 120.7 . . ?
F1 C15 C14 118.63(9) . . ?
F1 C15 C16 117.97(9) . . ?
C16 C15 C14 123.40(10) . . ?
O2 C10 C7 122.56(9) . . ?
N1 C10 C7 125.96(9) . . ?
N1 C10 O2 111.48(9) . . ?
C1 O2 C10 118.73(8) . . ?
C9 N1 C10 113.76(9) . . ?
N1 C9 H9 116.0 . . ?
N2 C9 N1 127.96(10) . . ?
N2 C9 H9 116.0 . . ?
C9 N2 C8 116.13(9) . . ?
C20 C25 H25 120.1 . . ?
C24 C25 C20 119.77(10) . . ?
C24 C25 H25 120.1 . . ?
C23 C24 C25 118.71(10) . . ?
C23 C24 H24 120.6 . . ?
C25 C24 H24 120.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C4 C5 C6 8.95(14) . . . . ?
O1 C4 C5 C1 -174.56(10) . . . . ?
C13 C3 C11 C4 71.45(11) . . . . ?
C13 C3 C2 C1 -69.25(11) . . . . ?
C3 C11 C4 O1 -158.86(10) . . . . ?
C3 C11 C4 C5 21.74(13) . . . . ?
C3 C2 C1 C5 -29.56(14) . . . . ?
C3 C2 C1 O2 149.82(8) . . . . ?
C11 C3 C2 C1 51.59(11) . . . . ?
C11 C4 C5 C6 -171.66(8) . . . . ?
C11 C4 C5 C1 4.84(13) . . . . ?
C4 C5 C6 C7 -175.22(8) . . . . ?
C4 C5 C6 C14 60.93(11) . . . . ?
C4 C5 C1 C2 -0.45(15) . . . . ?
C4 C5 C1 O2 -179.76(8) . . . . ?
C5 C6 C7 C8 174.83(9) . . . . ?
C5 C6 C7 C10 -8.47(13) . . . . ?
C5 C6 C14 C19 -119.49(10) . . . . ?
C5 C6 C14 C15 60.18(12) . . . . ?
C5 C1 O2 C10 -2.68(14) . . . . ?
C6 C5 C1 C2 175.86(9) . . . . ?
C6 C5 C1 O2 -3.45(15) . . . . ?
C6 C7 C8 N3 -2.98(14) . . . . ?
C6 C7 C8 N2 177.55(9) . . . . ?
C6 C7 C10 O2 3.64(15) . . . . ?
C6 C7 C10 N1 -175.64(9) . . . . ?
C6 C14 C19 C18 -179.29(9) . . . . ?
C6 C14 C15 F1 0.90(14) . . . . ?
C6 C14 C15 C16 -179.57(9) . . . . ?
C7 C6 C14 C19 118.11(10) . . . . ?
C7 C6 C14 C15 -62.22(12) . . . . ?
C7 C8 N3 C20 169.36(9) . . . . ?
C7 C8 N2 C9 -1.52(14) . . . . ?
C7 C10 O2 C1 2.54(14) . . . . ?
C7 C10 N1 C9 -2.12(15) . . . . ?
C8 C7 C10 O2 -179.35(8) . . . . ?
C8 C7 C10 N1 1.36(15) . . . . ?
C8 N3 C20 C21 -126.31(11) . . . . ?
C8 N3 C20 C25 56.82(15) . . . . ?
N3 C8 N2 C9 178.99(9) . . . . ?
N3 C20 C21 C22 -176.39(10) . . . . ?
N3 C20 C25 C24 176.71(10) . . . . ?
C20 C21 C22 C23 -0.38(17) . . . . ?
C20 C25 C24 C23 -0.51(16) . . . . ?
C21 C20 C25 C24 -0.08(16) . . . . ?
C21 C22 C23 F2 179.57(10) . . . . ?
C21 C22 C23 C24 -0.23(18) . . . . ?
C22 C23 C24 C25 0.68(18) . . . . ?
F2 C23 C24 C25 -179.12(10) . . . . ?
C12 C3 C11 C4 -167.52(8) . . . . ?
C12 C3 C2 C1 170.59(8) . . . . ?
C2 C3 C11 C4 -49.13(11) . . . . ?
C2 C1 O2 C10 177.92(8) . . . . ?
C1 C5 C6 C7 8.45(13) . . . . ?
C1 C5 C6 C14 -115.40(10) . . . . ?
C14 C6 C7 C8 -62.05(12) . . . . ?
C14 C6 C7 C10 114.66(10) . . . . ?
C14 C19 C18 C17 -1.24(16) . . . . ?
C19 C14 C15 F1 -179.42(9) . . . . ?
C19 C14 C15 C16 0.12(15) . . . . ?
C19 C18 C17 C16 0.30(17) . . . . ?
C18 C17 C16 C15 0.80(16) . . . . ?
C17 C16 C15 F1 178.51(9) . . . . ?
C17 C16 C15 C14 -1.03(16) . . . . ?
C15 C14 C19 C18 1.02(15) . . . . ?
C10 C7 C8 N3 -179.92(9) . . . . ?
C10 C7 C8 N2 0.60(14) . . . . ?
C10 N1 C9 N2 1.05(16) . . . . ?
O2 C10 N1 C9 178.53(8) . . . . ?
N1 C10 O2 C1 -178.08(8) . . . . ?
N1 C9 N2 C8 0.68(16) . . . . ?
N2 C8 N3 C20 -11.14(15) . . . . ?
C25 C20 C21 C22 0.54(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_3e
_database_code_depnum_ccdc_archive 'CCDC 2219311'
loop_
_audit_author_name
_audit_author_address
'Sizwe Zamisa'
;University of KwaZulu Natal
South Africa
;
_audit_update_record             
;
2023-07-10 deposited with the CCDC.	2023-07-12 downloaded from the CCDC.
;
_audit_creation_date             2023-06-22
_audit_creation_method           
;
Olex2 1.5-dev
(compiled 2023.04.26 svn.r751481ca for OlexSys, GUI svn.r6697)
;
_chemical_formula_moiety         'C25 H20 Cl F2 N3 O2'
_chemical_formula_sum            'C25 H20 Cl F2 N3 O2'
_chemical_formula_weight         467.906
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
Cl 0.14908 0.15974 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55740 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
F 0.01756 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.2220(1)
_cell_length_b                   10.4778(2)
_cell_length_c                   14.4403(3)
_cell_angle_alpha                75.338(1)
_cell_angle_beta                 82.465(1)
_cell_angle_gamma                85.928(1)
_cell_volume                     1047.18(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.60
_cell_measurement_theta_min      2.77
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_description       block
_exptl_crystal_F_000             484.629
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.362
_exptl_crystal_size_mid          0.312
_exptl_crystal_size_min          0.244
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.9971
_diffrn_reflns_Laue_measured_fraction_max 0.9759
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21374
_diffrn_reflns_point_group_measured_fraction_full 0.9971
_diffrn_reflns_point_group_measured_fraction_max 0.9759
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.65
_diffrn_reflns_theta_min         1.47
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9971
_diffrn_measured_fraction_theta_max 0.9759
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              14
_reflns_limit_k_min              -13
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                4808
_reflns_number_total             5268
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT-plus (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-dev (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.3907
_refine_diff_density_min         -0.2972
_refine_diff_density_rms         0.0503
_refine_ls_d_res_high            0.7411
_refine_ls_d_res_low             13.8737
_refine_ls_extinction_coef       0.0046(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0632
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    43
_refine_ls_number_parameters     323
_refine_ls_number_reflns         5268
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.0532
_refine_ls_shift/su_max          0.0010
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0449P)²+0.3678P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0911
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C20-C21 \\sim C20a-C21a
 with sigma of 0.02
 C20-C25 \\sim C20a-C25a
 with sigma of 0.02
 C20-N3 \\sim C20a-N3
 with sigma of 0.02
 C21-C22 \\sim C21a-C22a
 with sigma of 0.02
 C22-C23 \\sim C22a-C23a
 with sigma of 0.02
 C22-Cl1 \\sim C22a-Cl1a
 with sigma of 0.02
 C23-C24 \\sim C23a-C24a
 with sigma of 0.02
 C23-F2 \\sim C23a-F2a
 with sigma of 0.02
 C25-C24 \\sim C25a-C24a
 with sigma of 0.02
 C20-C22 \\sim C20a-C22a
 with sigma of 0.04
 C20-C24 \\sim C20a-C24a
 with sigma of 0.04
 C21-C23 \\sim C21a-C23a
 with sigma of 0.04
 C21-C25 \\sim C21a-C25a
 with sigma of 0.04
 C21-N3 \\sim C21a-N3
 with sigma of 0.04
 C21-Cl1 \\sim C21a-Cl1a
 with sigma of 0.04
 C22-C24 \\sim C22a-C24a
 with sigma of 0.04
 C22-F2 \\sim C22a-F2a
 with sigma of 0.04
 C23-C25 \\sim C23a-C25a
 with sigma of 0.04
 C23-Cl1 \\sim C23a-Cl1a
 with sigma of 0.04
 C25-N3 \\sim C25a-N3
 with sigma of 0.04
 C24-F2 \\sim C24a-F2a
 with sigma of 0.04
 C21a-N3 \\sim N3-C25a
 with sigma of 0.001
 C21a-Cl1a \\sim Cl1a-C23a
 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
C20a \\sim C25a \\sim F2a \\sim C21a \\sim C24a \\sim C22a \\sim Cl1a \\sim
C23a: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within
2A
4. Others
 Sof(H3b)=Sof(C20a)=Sof(C21a)=Sof(H21a)=Sof(C22a)=Sof(C23a)=Sof(C24a)=
 Sof(H24a)=Sof(C25a)=Sof(H25a)=Sof(F2a)=Sof(Cl1a)=1-FVAR(1)
 Sof(C20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(C23)=Sof(C25)=Sof(H25)=Sof(C24)=
 Sof(H24)=Sof(H3a)=Sof(F2)=Sof(Cl1)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C7(H7)
5.b Secondary CH2 refined with riding coordinates:
 C4(H4a,H4b), C2(H2a,H2b)
5.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C10(H10), C14(H14), C15(H15), C16(H16), C17(H17), C25(H25),
 C24(H24), N3(H3a), N3(H3b), C21a(H21a), C24a(H24a), C25a(H25a)
5.d Fitted hexagon refined as free rotating group:
 C20a(C21a,C22a,C23a,C24a,C25a)
5.e Idealised Me refined as rotating group:
 C19(H19a,H19b,H19c), C18(H18a,H18b,H18c)
;
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_refinement_flags_posn
_atom_site_refinement_flags_occupancy
_atom_site_disorder_group
C19 C -0.07058(16) 0.66988(11) 1.00484(8) 0.0247(2) Uani 1.000000 . . .
H19a H -0.0747(7) 0.6591(8) 0.93969(18) 0.0371(3) Uiso 1.000000 GR . .
H19b H -0.0705(6) 0.5830(4) 1.0505(5) 0.0371(3) Uiso 1.000000 GR . .
H19c H -0.18036(16) 0.7229(5) 1.0227(7) 0.0371(3) Uiso 1.000000 GR . .
C3 C 0.10709(16) 0.73964(10) 1.00733(7) 0.0212(2) Uani 1.000000 . . .
C4 C 0.28115(16) 0.65967(11) 0.97704(8) 0.0221(2) Uani 1.000000 . . .
H4a H 0.39338(16) 0.69703(11) 0.99113(8) 0.0266(3) Uiso 1.000000 R . .
H4b H 0.27351(16) 0.56761(11) 1.01660(8) 0.0266(3) Uiso 1.000000 R . .
C5 C 0.30506(14) 0.65806(10) 0.87163(8) 0.0197(2) Uani 1.000000 . . .
C6 C 0.23024(14) 0.77265(10) 0.80247(7) 0.01725(19) Uani 1.000000 . . .
C7 C 0.25334(14) 0.77047(10) 0.69756(7) 0.01660(19) Uani 1.000000 . . .
H7 H 0.38544(14) 0.74264(10) 0.67902(7) 0.0199(2) Uiso 1.000000 R . .
C8 C 0.21406(14) 0.90816(10) 0.63712(7) 0.01663(19) Uani 1.000000 . . .
C9 C 0.25819(14) 0.94647(10) 0.53582(7) 0.01745(19) Uani 1.000000 . . .
C20 C 0.40193(19) 0.86295(13) 0.39162(8) 0.0181(3) Uani 0.9530(12) D P 1
C21 C 0.36488(17) 0.97193(12) 0.31712(8) 0.0189(2) Uani 0.9530(12) D P 1
H21 H 0.30154(17) 1.04880(12) 0.33090(8) 0.0227(3) Uiso 0.9530(12) R P 1
C22 C 0.42175(15) 0.96656(11) 0.22266(8) 0.0194(2) Uani 0.9530(12) D P 1
C23 C 0.51677(16) 0.85622(12) 0.20214(8) 0.0228(2) Uani 0.9530(12) D P 1
C10 C 0.12459(15) 1.14952(10) 0.53347(8) 0.0210(2) Uani 1.000000 . . .
H10 H 0.08962(15) 1.23436(10) 0.49647(8) 0.0252(2) Uiso 1.000000 R . .
C11 C 0.12700(14) 1.00636(10) 0.67738(7) 0.01736(19) Uani 1.000000 . . .
C1 C 0.14467(14) 0.87372(10) 0.83455(7) 0.0179(2) Uani 1.000000 . . .
C2 C 0.10893(16) 0.87791(10) 0.93790(7) 0.0205(2) Uani 1.000000 . . .
H2a H -0.01301(16) 0.92448(10) 0.94885(7) 0.0246(2) Uiso 1.000000 R . .
H2b H 0.20686(16) 0.92901(10) 0.95239(7) 0.0246(2) Uiso 1.000000 R . .
C18 C 0.1119(2) 0.75354(13) 1.10998(8) 0.0324(3) Uani 1.000000 . . .
H18a H -0.0006(7) 0.8031(9) 1.1292(3) 0.0485(4) Uiso 1.000000 GR . .
H18b H 0.1164(15) 0.66569(13) 1.15424(14) 0.0485(4) Uiso 1.000000 GR . .
H18c H 0.2229(8) 0.8008(9) 1.11221(18) 0.0485(4) Uiso 1.000000 GR . .
C12 C 0.12293(14) 0.67134(9) 0.68120(7) 0.01718(19) Uani 1.000000 . . .
C13 C 0.18554(15) 0.57319(10) 0.63458(7) 0.0207(2) Uani 1.000000 . . .
C14 C 0.07169(18) 0.48164(11) 0.61947(8) 0.0271(2) Uani 1.000000 . . .
H14 H 0.12130(18) 0.41608(11) 0.58710(8) 0.0325(3) Uiso 1.000000 R . .
C15 C -0.11649(18) 0.48798(12) 0.65273(9) 0.0285(2) Uani 1.000000 . . .
H15 H -0.19771(18) 0.42620(12) 0.64318(9) 0.0342(3) Uiso 1.000000 R . .
C16 C -0.18724(16) 0.58431(11) 0.70007(8) 0.0249(2) Uani 1.000000 . . .
H16 H -0.31650(16) 0.58848(11) 0.72284(8) 0.0299(3) Uiso 1.000000 R . .
C17 C -0.06774(15) 0.67471(10) 0.71395(8) 0.0203(2) Uani 1.000000 . . .
H17 H -0.11705(15) 0.74020(10) 0.74646(8) 0.0244(2) Uiso 1.000000 R . .
C25 C 0.49561(18) 0.75034(14) 0.36971(10) 0.0224(2) Uani 0.9530(12) D P 1
H25 H 0.51938(18) 0.67558(14) 0.42040(10) 0.0269(3) Uiso 0.9530(12) R P 1
C24 C 0.55384(18) 0.74688(12) 0.27502(9) 0.0254(2) Uani 0.9530(12) D P 1
H24 H 0.61808(18) 0.67077(12) 0.26043(9) 0.0305(3) Uiso 0.9530(12) R P 1
N3 N 0.34878(13) 0.85608(9) 0.49005(6) 0.02011(18) Uani 1.000000 D . .
H3a H 0.37905(13) 0.78045(9) 0.52903(6) 0.0241(2) Uiso 0.9530(12) R P 1
H3b H 0.37375(13) 0.77687(9) 0.52583(6) 0.0241(2) Uiso 0.0470(12) R P 2
N2 N 0.21356(13) 1.06759(9) 0.48373(6) 0.02038(18) Uani 1.000000 . . .
N1 N 0.07859(13) 1.12765(9) 0.62819(7) 0.02046(18) Uani 1.000000 . . .
O2 O 0.08030(11) 0.98772(7) 0.77504(5) 0.02045(16) Uani 1.000000 . . .
O1 O 0.38821(12) 0.56680(8) 0.84279(6) 0.02731(18) Uani 1.000000 . . .
F2 F 0.57280(12) 0.85530(8) 0.10918(5) 0.03322(19) Uani 0.9530(12) D P 1
F1 F 0.37181(10) 0.56605(7) 0.60109(5) 0.02762(16) Uani 1.000000 . . .
Cl1 Cl 0.36793(4) 1.09875(3) 0.129595(19) 0.02520(9) Uani 0.9530(12) D P 1
C20a C 0.404(5) 0.8794(13) 0.3928(2) 0.048(9) Uiso 0.0470(12) D P 2
C21a C 0.484(4) 0.7769(12) 0.3540(3) 0.045(8) Uiso 0.0470(12) DG P 2
H21a H 0.516(4) 0.6947(12) 0.3955(3) 0.4(9) Uiso 0.0470(12) R P 2
C22a C 0.516(3) 0.7946(10) 0.2546(3) 0.024(5) Uiso 0.0470(12) DG P 2
C23a C 0.468(3) 0.9148(8) 0.1940(2) 0.019(4) Uiso 0.0470(12) DG P 2
C24a C 0.388(4) 1.0173(9) 0.2327(3) 0.051(7) Uiso 0.0470(12) DG P 2
H24a H 0.355(4) 1.0995(9) 0.1913(3) 0.061(8) Uiso 0.0470(12) R P 2
C25a C 0.356(5) 0.9996(12) 0.3321(3) 0.046(9) Uiso 0.0470(12) DG P 2
H25a H 0.301(5) 1.0697(12) 0.3586(3) 0.056(10) Uiso 0.0470(12) R P 2
F2a F 0.496(3) 0.939(2) 0.0940(14) 0.057(5) Uiso 0.0470(12) D P 2
Cl1a Cl 0.5693(12) 0.6717(8) 0.2117(5) 0.051(2) Uiso 0.0470(12) D P 2


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
C19 H19a 0.9800 . ?
C19 H19b 0.9800 . ?
C19 H19c 0.9800 . ?
C19 C3 1.5300(16) . ?
C3 C4 1.5380(15) . ?
C3 C2 1.5389(14) . ?
C3 C18 1.5306(15) . ?
C4 H4a 0.9900 . ?
C4 H4b 0.9900 . ?
C4 C5 1.5135(14) . ?
C5 C6 1.4742(14) . ?
C5 O1 1.2260(13) . ?
C6 C7 1.5079(13) . ?
C6 C1 1.3410(14) . ?
C7 H7 1.0000 . ?
C7 C8 1.5142(13) . ?
C7 C12 1.5308(14) . ?
C8 C9 1.4147(14) . ?
C8 C11 1.3809(14) . ?
C9 N3 1.3701(13) . ?
C9 N2 1.3426(13) . ?
C20 C21 1.3939(15) . ?
C20 C25 1.4034(16) . ?
C20 N3 1.4079(13) . ?
C21 H21 0.9500 . ?
C21 C22 1.3861(16) . ?
C22 C23 1.3794(16) . ?
C22 Cl1 1.7302(11) . ?
C23 C24 1.3826(16) . ?
C23 F2 1.3525(13) . ?
C10 H10 0.9500 . ?
C10 N2 1.3335(14) . ?
C10 N1 1.3291(14) . ?
C11 N1 1.3368(13) . ?
C11 O2 1.3733(12) . ?
C1 C2 1.4921(14) . ?
C1 O2 1.3738(12) . ?
C2 H2a 0.9900 . ?
C2 H2b 0.9900 . ?
C18 H18a 0.9800 . ?
C18 H18b 0.9800 . ?
C18 H18c 0.9800 . ?
C12 C13 1.3856(14) . ?
C12 C17 1.3971(15) . ?
C13 C14 1.3816(15) . ?
C13 F1 1.3720(13) . ?
C14 H14 0.9500 . ?
C14 C15 1.3835(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.3898(17) . ?
C16 H16 0.9500 . ?
C16 C17 1.3927(15) . ?
C17 H17 0.9500 . ?
C25 H25 0.9500 . ?
C25 C24 1.3856(16) . ?
C24 H24 0.9500 . ?
N3 H3a 0.8800 . ?
N3 H3b 0.8800 . ?
N3 C20a 1.373(3) . ?
C20a C21a 1.3900 . ?
C20a C25a 1.3900 . ?
C21a H21a 0.9500 . ?
C21a C22a 1.3900 . ?
C22a C23a 1.3900 . ?
C22a Cl1a 1.569(3) . ?
C23a C24a 1.3900 . ?
C23a F2a 1.390(19) . ?
C24a H24a 0.9500 . ?
C24a C25a 1.3900 . ?
C25a H25a 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H19b C19 H19a 109.5 . . ?
H19c C19 H19a 109.5 . . ?
H19c C19 H19b 109.5 . . ?
C3 C19 H19a 109.5 . . ?
C3 C19 H19b 109.5 . . ?
C3 C19 H19c 109.5 . . ?
C4 C3 C19 110.33(9) . . ?
C2 C3 C19 110.68(9) . . ?
C2 C3 C4 108.32(9) . . ?
C18 C3 C19 108.53(9) . . ?
C18 C3 C4 109.98(9) . . ?
C18 C3 C2 108.99(9) . . ?
H4a C4 C3 108.74(6) . . ?
H4b C4 C3 108.74(6) . . ?
H4b C4 H4a 107.6 . . ?
C5 C4 C3 114.06(9) . . ?
C5 C4 H4a 108.74(6) . . ?
C5 C4 H4b 108.74(6) . . ?
C6 C5 C4 118.05(9) . . ?
O1 C5 C4 121.97(9) . . ?
O1 C5 C6 119.96(9) . . ?
C7 C6 C5 117.94(8) . . ?
C1 C6 C5 119.40(9) . . ?
C1 C6 C7 122.66(9) . . ?
H7 C7 C6 108.74(5) . . ?
C8 C7 C6 109.14(8) . . ?
C8 C7 H7 108.74(5) . . ?
C12 C7 C6 110.15(8) . . ?
C12 C7 H7 108.74(5) . . ?
C12 C7 C8 111.27(8) . . ?
C9 C8 C7 123.59(9) . . ?
C11 C8 C7 121.92(9) . . ?
C11 C8 C9 114.48(9) . . ?
N3 C9 C8 118.43(9) . . ?
N2 C9 C8 122.15(9) . . ?
N2 C9 N3 119.42(9) . . ?
C25 C20 C21 119.57(11) . . ?
N3 C20 C21 124.22(11) . . ?
N3 C20 C25 116.21(10) . . ?
H21 C21 C20 120.47(7) . . ?
C22 C21 C20 119.06(11) . . ?
C22 C21 H21 120.47(7) . . ?
C23 C22 C21 120.81(10) . . ?
Cl1 C22 C21 119.35(9) . . ?
Cl1 C22 C23 119.82(9) . . ?
C24 C23 C22 120.95(10) . . ?
F2 C23 C22 119.19(10) . . ?
F2 C23 C24 119.85(10) . . ?
N2 C10 H10 115.85(6) . . ?
N1 C10 H10 115.85(6) . . ?
N1 C10 N2 128.29(10) . . ?
N1 C11 C8 125.27(9) . . ?
O2 C11 C8 122.24(9) . . ?
O2 C11 N1 112.49(9) . . ?
C2 C1 C6 124.89(9) . . ?
O2 C1 C6 123.54(9) . . ?
O2 C1 C2 111.57(8) . . ?
C1 C2 C3 112.81(8) . . ?
H2a C2 C3 109.03(6) . . ?
H2a C2 C1 109.03(6) . . ?
H2b C2 C3 109.03(6) . . ?
H2b C2 C1 109.03(6) . . ?
H2b C2 H2a 107.8 . . ?
H18a C18 C3 109.5 . . ?
H18b C18 C3 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 C3 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?
C13 C12 C7 122.65(9) . . ?
C17 C12 C7 121.13(9) . . ?
C17 C12 C13 116.22(9) . . ?
C14 C13 C12 124.00(10) . . ?
F1 C13 C12 118.31(9) . . ?
F1 C13 C14 117.69(9) . . ?
H14 C14 C13 120.88(7) . . ?
C15 C14 C13 118.24(10) . . ?
C15 C14 H14 120.88(6) . . ?
H15 C15 C14 119.85(6) . . ?
C16 C15 C14 120.30(10) . . ?
C16 C15 H15 119.85(7) . . ?
H16 C16 C15 120.16(7) . . ?
C17 C16 C15 119.69(11) . . ?
C17 C16 H16 120.16(7) . . ?
C16 C17 C12 121.55(10) . . ?
H17 C17 C12 119.23(6) . . ?
H17 C17 C16 119.23(7) . . ?
H25 C25 C20 119.60(7) . . ?
C24 C25 C20 120.79(12) . . ?
C24 C25 H25 119.60(8) . . ?
C25 C24 C23 118.80(11) . . ?
H24 C24 C23 120.60(7) . . ?
H24 C24 C25 120.60(8) . . ?
C20 N3 C9 131.31(9) . . ?
H3a N3 C9 114.34(6) . . ?
H3a N3 C20 114.34(6) . . ?
H3b N3 C9 117.44(6) . . ?
H3b N3 C20 111.11(6) . . ?
H3b N3 H3a 5.3 . . ?
C20a N3 C9 125.12(18) . . ?
C20a N3 C20 7.2(9) . . ?
C20a N3 H3a 120.4(2) . . ?
C20a N3 H3b 117.44(17) . . ?
C10 N2 C9 115.79(9) . . ?
C11 N1 C10 113.96(9) . . ?
C1 O2 C11 118.13(8) . . ?
C21a C20a N3 119.7 . . ?
C25a C20a N3 119.7 . . ?
C25a C20a C21a 120.0 . . ?
H21a C21a C20a 120.00(12) . . ?
C22a C21a C20a 120.0 . . ?
C22a C21a H21a 120.00(12) . . ?
C23a C22a C21a 120.0 . . ?
Cl1a C22a C21a 119.4(2) . . ?
Cl1a C22a C23a 119.5(2) . . ?
C24a C23a C22a 120.0 . . ?
F2a C23a C22a 123.0(11) . . ?
F2a C23a C24a 117.0(11) . . ?
H24a C24a C23a 120.00(12) . . ?
C25a C24a C23a 120.0 . . ?
C25a C24a H24a 120.00(12) . . ?
C24a C25a C20a 120.0 . . ?
H25a C25a C20a 120.00(12) . . ?
H25a C25a C24a 120.00(12) . . ?

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
C19 C3 C4 C5 69.23(9) . . . . ?
C19 C3 C2 C1 -72.74(9) . . . . ?
C3 C4 C5 C6 28.98(11) . . . . ?
C3 C4 C5 O1 -153.00(9) . . . . ?
C3 C2 C1 C6 -22.68(12) . . . . ?
C3 C2 C1 O2 157.90(9) . . . . ?
C4 C5 C6 C7 -179.68(9) . . . . ?
C4 C5 C6 C1 0.14(11) . . . . ?
C5 C6 C7 C8 -165.48(9) . . . . ?
C5 C6 C7 C12 72.08(9) . . . . ?
C5 C6 C1 C2 -3.27(12) . . . . ?
C5 C6 C1 O2 176.09(9) . . . . ?
C6 C7 C8 C9 167.12(8) . . . . ?
C6 C7 C8 C11 -14.45(10) . . . . ?
C6 C7 C12 C13 -127.76(8) . . . . ?
C6 C7 C12 C17 51.59(9) . . . . ?
C6 C1 O2 C11 -8.67(12) . . . . ?
C7 C8 C9 N3 -2.96(11) . . . . ?
C7 C8 C9 N2 176.77(9) . . . . ?
C7 C8 C11 N1 -176.11(9) . . . . ?
C7 C8 C11 O2 3.80(11) . . . . ?
C7 C12 C13 C14 179.42(10) . . . . ?
C7 C12 C13 F1 -0.66(10) . . . . ?
C7 C12 C17 C16 -179.50(9) . . . . ?
C8 C9 N3 C20 176.50(10) . . . . ?
C8 C9 N3 C20a -179(2) . . . . ?
C8 C9 N2 C10 -0.14(11) . . . . ?
C8 C11 N1 C10 -1.09(12) . . . . ?
C8 C11 O2 C1 8.68(11) . . . . ?
C9 N3 C20 C21 -1.40(14) . . . . ?
C9 N3 C20 C25 179.54(13) . . . . ?
C9 N3 C20a C21a -175.7(13) . . . . ?
C9 N3 C20a C25a -5(2) . . . . ?
C9 N2 C10 N1 1.82(11) . . . . ?
C20 C21 C22 C23 -1.18(13) . . . . ?
C20 C21 C22 Cl1 177.38(9) . . . . ?
C20 C25 C24 C23 -0.49(14) . . . . ?
C20 N3 C20a C21a -25(12) . . . . ?
C20 N3 C20a C25a 146(12) . . . . ?
C21 C22 C23 C24 1.59(13) . . . . ?
C21 C22 C23 F2 -178.92(11) . . . . ?
C22 C23 C24 C25 -0.73(14) . . . . ?
C10 N1 C11 O2 179.00(9) . . . . ?
C11 O2 C1 C2 170.77(9) . . . . ?
C12 C13 C14 C15 0.05(13) . . . . ?
C12 C17 C16 C15 0.10(12) . . . . ?
C13 C14 C15 C16 -0.07(13) . . . . ?
C14 C15 C16 C17 -0.00(13) . . . . ?
N3 C20a C21a C22a 171.1(9) . . . . ?
N3 C20a C25a C24a -171.1(9) . . . . ?
C20a C21a C22a C23a -0(2) . . . . ?
C20a C21a C22a Cl1a -168.3(10) . . . . ?
C20a C25a C24a C23a -0(2) . . . . ?
C21a C22a C23a C24a 0(2) . . . . ?
C21a C22a C23a F2a -179.9(14) . . . . ?
C22a C23a C24a C25a 0(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_id
C20 C21 1 1
C20 C22 1 10
C20 C25 1 2
C20 C24 1 11
C20 N3 1 3
C21 C22 1 4
C21 C23 1 12
C21 C25 1 13
C21 N3 1 14
C21 Cl1 1 15
C22 C23 1 5
C22 C24 1 16
C22 F2 1 17
C22 Cl1 1 6
C23 C25 1 18
C23 C24 1 7
C23 F2 1 8
C23 Cl1 1 19
C25 C24 1 9
C25 N3 1 20
C24 F2 1 21
N3 C25a 1 22
C20a N3 1 3
C20a C21a 1 1
C20a C22a 1 10
C20a C24a 1 11
C20a C25a 1 2
C21a N3 1 14
C21a N3 1 22
C21a C22a 1 4
C21a C23a 1 12
C21a C25a 1 13
C21a Cl1a 1 15
C21a Cl1a 1 23
C22a C23a 1 5
C22a C24a 1 16
C22a F2a 1 17
C22a Cl1a 1 6
C23a C24a 1 7
C23a C25a 1 18
C23a F2a 1 8
C23a Cl1a 1 19
C24a F2a 1 21
C25a N3 1 20
C25a C24a 1 9
Cl1a C23a 1 23

loop_
_restr_equal_distance_class_class_id
_restr_equal_distance_class_target_weight_param
_restr_equal_distance_class_average
_restr_equal_distance_class_esd
_restr_equal_distance_class_diff_max
1 0.0200 1.3920 0.0020 0.0020
2 0.0200 1.3967 0.0067 0.0067
3 0.0200 1.3903 0.0176 0.0176
4 0.0200 1.3880 0.0020 0.0020
5 0.0200 1.3847 0.0053 0.0053
6 0.0200 1.6496 0.0807 0.0807
7 0.0200 1.3863 0.0037 0.0037
8 0.0200 1.3715 0.0190 0.0190
9 0.0200 1.3878 0.0022 0.0022
10 0.0400 2.4018 0.0057 0.0057
11 0.0400 2.4162 0.0087 0.0087
12 0.0400 2.4061 0.0014 0.0014
13 0.0400 2.4124 0.0048 0.0048
14 0.0400 2.4324 0.0439 0.0439
15 0.0400 2.6262 0.0694 0.0694
16 0.0400 2.4054 0.0021 0.0021
17 0.0400 2.4000 0.0438 0.0438
18 0.0400 2.3951 0.0124 0.0124
19 0.0400 2.6271 0.0692 0.0692
20 0.0400 2.3881 0.0014 0.0014
21 0.0400 2.3687 0.0017 0.0017
22 0.0010 2.3890 0.0005 0.0005
23 0.0010 2.5573 0.0005 0.0005

loop_
_restr_U_similar_atom_site_label_1
_restr_U_similar_atom_site_label_2
_restr_U_similar_weight_param
C20a C21a 0.0100
C20a C25a 0.0100
C21a C22a 0.0100
C22a C23a 0.0100
C22a Cl1a 0.0200
C23a C24a 0.0100
C23a F2a 0.0200
C24a C25a 0.0100

####################################################################### 
# 
# 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_3j
_database_code_depnum_ccdc_archive 'CCDC 2219313'
loop_
_audit_author_name
_audit_author_address
'Sizwe Zamisa'
;University of KwaZulu Natal
South Africa
;
_audit_update_record             
;
2023-07-10 deposited with the CCDC.	2023-07-12 downloaded from the CCDC.
;
_audit_creation_date             2023-06-23
_audit_creation_method           
;
Olex2 1.5-dev
(compiled 2023.04.26 svn.r751481ca for OlexSys, GUI svn.r6697)
;
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C35 H30 F Fe N3 O2, C3 H6 O'
_chemical_formula_sum            'C38 H36 F Fe N3 O3'
_chemical_formula_weight         657.571
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
F 0.01756 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
Fe 0.34785 0.84958 11.76950 7.35730 3.52220 2.30450 4.76110 0.30720 15.35350
76.88050 1.03690 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   11.1910(3)
_cell_length_b                   10.9002(3)
_cell_length_c                   25.9816(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.846(2)
_cell_angle_gamma                90
_cell_volume                     3139.67(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8677
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      27.12
_cell_measurement_theta_min      2.62
_exptl_absorpt_coefficient_mu    0.530
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker)'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             1378.300
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.9972
_diffrn_reflns_Laue_measured_fraction_max 0.9566
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            22501
_diffrn_reflns_point_group_measured_fraction_full 0.9972
_diffrn_reflns_point_group_measured_fraction_max 0.9566
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.18
_diffrn_reflns_theta_min         1.90
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9972
_diffrn_measured_fraction_theta_max 0.9566
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -13
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              33
_reflns_limit_l_min              -10
_reflns_number_gt                5505
_reflns_number_total             6680
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-dev (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.5040
_refine_diff_density_min         -0.4195
_refine_diff_density_rms         0.0746
_refine_ls_d_res_high            0.7779
_refine_ls_d_res_low             10.7279
_refine_ls_goodness_of_fit_ref   1.0469
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    72
_refine_ls_number_parameters     443
_refine_ls_number_reflns         6680
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      1.0443
_refine_ls_shift/su_max          -0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0360P)²+1.7535P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0836
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N3-H3
 0.88 with sigma of 0.001
 O1S-C2S \\sim O1t-C2t
 with sigma of 0.02
 C1S-C2S \\sim C1t-C2t
 with sigma of 0.02
 C2S-C3S \\sim C2t-C3t
 with sigma of 0.02
 O1S-C1S \\sim O1t-C1t
 with sigma of 0.04
 O1S-C3S \\sim O1t-C3t
 with sigma of 0.04
 C1S-C3S \\sim C1t-C3t
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
O1t \\sim C2t \\sim C1t \\sim C3t: within 2A with sigma of 0.001 and sigma for
terminal atoms of 0.002 within 2A
4. Others
 Sof(F1)=Sof(O1t)=Sof(C2t)=Sof(C1t)=Sof(C3t)=Sof(H1ta)=Sof(H1tb)=Sof(H1tc)=
 Sof(H3ta)=Sof(H3tb)=Sof(H3tc)=Sof(H13)=Sof(H1ta)=Sof(H1tb)=Sof(H1tc)=Sof(H3ta)=
 Sof(H3tb)=Sof(H3tc)=1-FVAR(1)
 Sof(F1A)=Sof(H17)=Sof(O1S)=Sof(C2S)=Sof(H1Sb)=Sof(H1Sc)=Sof(H1Sa)=Sof(C1S)=
 Sof(H3Sc)=Sof(C3S)=Sof(H3Sa)=Sof(H3Sb)=Sof(H1Sa)=Sof(H1Sb)=Sof(H1Sc)=Sof(H3Sa)=
 Sof(H3Sb)=Sof(H3Sc)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C31(H31), C32(H32), C33(H33), C34(H34), C35(H35), C30(H30), C27(H27),
 C28(H28), C29(H29), C7(H7)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C4(H4a,H4b)
5.c Me refined with riding coordinates:
 C18(H18a,H18b,H18c), C19(H19a,H19b,H19c)
5.d Aromatic/amide H refined with riding coordinates:
 C21(H21), C10(H10), C16(H16), C15(H15), C14(H14), C25(H25), C24(H24),
 C23(H23), C17(H17), C13(H13)
5.e Idealised Me refined as rotating group:
 C1t(H1ta,H1tb,H1tc), C3t(H3ta,H3tb,H3tc), C1S(H1Sa,H1Sb,H1Sc), C3S(H3Sa,H3Sb,
 H3Sc)
;
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_refinement_flags_posn
_atom_site_refinement_flags_occupancy
_atom_site_disorder_group
Fe1 Fe 0.46194(2) 0.66301(2) 0.212439(9) 0.01556(8) Uani 1.000000 . . .
O1 O 1.10610(11) 0.33435(11) 0.16127(4) 0.0212(3) Uani 1.000000 . . .
O2 O 1.00882(10) 0.25673(11) -0.01794(4) 0.0173(3) Uani 1.000000 . . .
O1S O 0.87598(13) 0.59018(13) 0.16149(6) 0.0340(4) Uani 0.935(2) D P 1
N2 N 0.74297(12) 0.51237(13) -0.04208(5) 0.0163(3) Uani 1.000000 . . .
N1 N 0.87738(13) 0.36650(13) -0.07241(5) 0.0181(3) Uani 1.000000 . . .
C31 C 0.49020(18) 0.48273(16) 0.19556(7) 0.0250(4) Uani 1.000000 . . .
H31 H 0.50233(18) 0.44909(16) 0.16084(7) 0.0299(5) Uiso 1.000000 R . .
C32 C 0.58238(18) 0.52613(17) 0.23456(8) 0.0270(4) Uani 1.000000 . . .
H32 H 0.67077(18) 0.52803(17) 0.23211(8) 0.0324(5) Uiso 1.000000 R . .
C33 C 0.52656(18) 0.56671(17) 0.27749(7) 0.0260(4) Uani 1.000000 . . .
H33 H 0.56878(18) 0.60202(17) 0.31059(7) 0.0312(5) Uiso 1.000000 R . .
C34 C 0.40089(17) 0.54797(16) 0.26524(7) 0.0223(4) Uani 1.000000 . . .
H34 H 0.33874(17) 0.56850(16) 0.28812(7) 0.0268(5) Uiso 1.000000 R . .
C35 C 0.37786(17) 0.49579(16) 0.21479(7) 0.0217(4) Uani 1.000000 . . .
H35 H 0.29688(17) 0.47348(16) 0.19590(7) 0.0261(5) Uiso 1.000000 R . .
C30 C 0.35639(16) 0.77900(15) 0.16333(6) 0.0173(4) Uani 1.000000 . . .
H30 H 0.27777(16) 0.75737(15) 0.14217(6) 0.0207(4) Uiso 1.000000 R . .
C26 C 0.47291(15) 0.76634(15) 0.14721(6) 0.0165(4) Uani 1.000000 . . .
C27 C 0.55991(16) 0.80612(15) 0.18955(7) 0.0188(4) Uani 1.000000 . . .
H27 H 0.64937(16) 0.80764(15) 0.18991(7) 0.0225(4) Uiso 1.000000 R . .
C28 C 0.49691(17) 0.84235(16) 0.23116(7) 0.0206(4) Uani 1.000000 . . .
H28 H 0.53450(17) 0.87379(16) 0.26578(7) 0.0247(4) Uiso 1.000000 R . .
C29 C 0.37153(16) 0.82603(15) 0.21498(7) 0.0193(4) Uani 1.000000 . . .
H29 H 0.30548(16) 0.84344(15) 0.23627(7) 0.0232(4) Uiso 1.000000 R . .
C22 C 0.49929(15) 0.72224(15) 0.09607(6) 0.0157(3) Uani 1.000000 . . .
C21 C 0.60459(15) 0.65633(15) 0.09244(6) 0.0159(3) Uani 1.000000 . . .
H21 H 0.65912(15) 0.64025(15) 0.12303(6) 0.0191(4) Uiso 1.000000 R . .
C20 C 0.63135(15) 0.61355(15) 0.04470(6) 0.0148(3) Uani 1.000000 . . .
N3 N 0.73759(13) 0.54238(13) 0.04648(5) 0.0161(3) Uani 1.000000 D . .
H3 H 0.7764(14) 0.5346(17) 0.0781(3) 0.0194(4) Uiso 1.000000 DR . .
C9 C 0.78488(15) 0.48348(14) 0.00743(6) 0.0141(3) Uani 1.000000 . . .
C10 C 0.79035(16) 0.45056(15) -0.07845(6) 0.0178(4) Uani 1.000000 . . .
H10 H 0.75787(16) 0.46874(15) -0.11332(6) 0.0213(4) Uiso 1.000000 R . .
C11 C 0.91776(15) 0.34237(15) -0.02262(6) 0.0155(3) Uani 1.000000 . . .
C8 C 0.87581(15) 0.39399(15) 0.01982(6) 0.0142(3) Uani 1.000000 . . .
C7 C 0.92314(15) 0.35288(15) 0.07465(6) 0.0136(3) Uani 1.000000 . . .
H7 H 0.93803(15) 0.42780(15) 0.09681(6) 0.0163(4) Uiso 1.000000 R . .
C12 C 0.83387(15) 0.27128(15) 0.09845(6) 0.0153(3) Uani 1.000000 . . .
C17 C 0.78390(16) 0.30717(16) 0.14252(7) 0.0193(4) Uani 1.000000 . . .
C16 C 0.70481(17) 0.23225(17) 0.16482(7) 0.0246(4) Uani 1.000000 . . .
H16 H 0.67167(17) 0.25946(17) 0.19460(7) 0.0296(5) Uiso 1.000000 R . .
C15 C 0.67407(16) 0.11803(18) 0.14381(7) 0.0247(4) Uani 1.000000 . . .
H15 H 0.62068(16) 0.06641(18) 0.15935(7) 0.0297(5) Uiso 1.000000 R . .
C14 C 0.72151(16) 0.07925(17) 0.09997(7) 0.0235(4) Uani 1.000000 . . .
H14 H 0.70093(16) 0.00128(17) 0.08499(7) 0.0282(5) Uiso 1.000000 R . .
C13 C 0.79913(16) 0.15621(16) 0.07860(7) 0.0190(4) Uani 1.000000 . . .
C6 C 1.04273(15) 0.28884(15) 0.07362(6) 0.0142(3) Uani 1.000000 . . .
C1 C 1.07553(15) 0.24177(15) 0.03005(6) 0.0151(3) Uani 1.000000 . . .
C2 C 1.18696(15) 0.16952(16) 0.02632(6) 0.0175(3) Uani 1.000000 . . .
H2a H 1.16778(15) 0.10196(16) 0.00107(6) 0.0210(4) Uiso 1.000000 R . .
H2b H 1.24750(15) 0.22313(16) 0.01318(6) 0.0210(4) Uiso 1.000000 R . .
C3 C 1.24090(15) 0.11557(16) 0.07900(7) 0.0175(4) Uani 1.000000 . . .
C18 C 1.36840(16) 0.06829(17) 0.07494(7) 0.0232(4) Uani 1.000000 . . .
H18a H 1.41848(16) 0.13612(17) 0.06538(7) 0.0348(6) Uiso 1.000000 R . .
H18b H 1.40391(16) 0.03443(17) 0.10851(7) 0.0348(6) Uiso 1.000000 R . .
H18c H 1.36426(16) 0.00412(17) 0.04834(7) 0.0348(6) Uiso 1.000000 R . .
C4 C 1.24723(15) 0.21891(16) 0.11935(7) 0.0186(4) Uani 1.000000 . . .
H4a H 1.27633(15) 0.18431(16) 0.15403(7) 0.0224(4) Uiso 1.000000 R . .
H4b H 1.30711(15) 0.28035(16) 0.11126(7) 0.0224(4) Uiso 1.000000 R . .
C5 C 1.12815(15) 0.28312(15) 0.12172(6) 0.0155(3) Uani 1.000000 . . .
C19 C 1.16207(16) 0.00982(16) 0.09395(7) 0.0205(4) Uani 1.000000 . . .
H19a H 1.15913(16) -0.05518(16) 0.06775(7) 0.0308(6) Uiso 1.000000 R . .
H19b H 1.19642(16) -0.02294(16) 0.12789(7) 0.0308(6) Uiso 1.000000 R . .
H19c H 1.08026(16) 0.04001(16) 0.09577(7) 0.0308(6) Uiso 1.000000 R . .
C25 C 0.55189(15) 0.63868(15) -0.00048(6) 0.0165(3) Uani 1.000000 . . .
H25 H 0.56888(15) 0.61062(15) -0.03334(6) 0.0198(4) Uiso 1.000000 R . .
C24 C 0.44790(15) 0.70525(16) 0.00352(6) 0.0168(4) Uani 1.000000 . . .
H24 H 0.39409(15) 0.72301(16) -0.02711(6) 0.0202(4) Uiso 1.000000 R . .
C23 C 0.42037(15) 0.74654(15) 0.05093(7) 0.0169(3) Uani 1.000000 . . .
H23 H 0.34812(15) 0.79116(15) 0.05268(7) 0.0203(4) Uiso 1.000000 R . .
C1S C 0.9208(4) 0.7946(3) 0.14001(15) 0.0302(7) Uani 0.935(2) D P 1
C2S C 0.94141(19) 0.67889(19) 0.17042(9) 0.0247(5) Uani 0.935(2) D P 1
C3S C 1.0483(3) 0.6762(3) 0.21230(10) 0.0405(7) Uani 0.935(2) D P 1
F1A F 0.84162(10) 0.11809(10) 0.03471(4) 0.0235(3) Uani 0.935(2) . P 1
F1 F 0.7925(14) 0.4210(15) 0.1556(6) 0.023(4) Uiso 0.065(2) . P 2
H17 H 0.80463(16) 0.38499(16) 0.15763(7) 0.0231(4) Uiso 0.935(2) R P 1
O1t O 0.843(2) 0.659(2) 0.2060(9) 0.037(5) Uiso 0.065(2) D P 2
C2t C 0.937(3) 0.695(4) 0.1923(14) 0.036(5) Uiso 0.065(2) D P 2
C1t C 0.935(7) 0.775(7) 0.147(2) 0.036(5) Uiso 0.065(2) D P 2
C3t C 1.045(4) 0.670(6) 0.2297(16) 0.036(5) Uiso 0.065(2) D P 2
H13 H 0.83087(16) 0.12905(16) 0.04848(7) 0.0228(4) Uiso 0.065(2) R P 2
H1ta H 0.864(15) 0.829(18) 0.145(6) 0.053(8) Uiso 0.065(2) GR P 2
H1tb H 1.008(13) 0.825(19) 0.151(6) 0.053(8) Uiso 0.065(2) GR P 2
H1tc H 0.93(3) 0.726(7) 0.116(3) 0.053(8) Uiso 0.065(2) GR P 2
H3ta H 1.099(11) 0.615(18) 0.214(4) 0.053(8) Uiso 0.065(2) GR P 2
H3tb H 1.087(12) 0.747(6) 0.239(7) 0.053(8) Uiso 0.065(2) GR P 2
H3tc H 1.021(4) 0.63(2) 0.261(4) 0.053(8) Uiso 0.065(2) GR P 2
H1Sa H 0.8496(10) 0.7853(6) 0.1138(5) 0.0453(10) Uiso 0.935(2) GR P 1
H1Sb H 0.9076(16) 0.8623(4) 0.16343(18) 0.0453(10) Uiso 0.935(2) GR P 1
H1Sc H 0.9915(7) 0.8125(9) 0.1228(6) 0.0453(10) Uiso 0.935(2) GR P 1
H3Sa H 1.0455(9) 0.6015(8) 0.2331(4) 0.0607(11) Uiso 0.935(2) GR P 1
H3Sb H 1.1228(3) 0.6770(17) 0.19640(10) 0.0607(11) Uiso 0.935(2) GR P 1
H3Sc H 1.0462(9) 0.7483(9) 0.2347(4) 0.0607(11) Uiso 0.935(2) GR P 1


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
Fe1 C31 2.0475(18) . y
Fe1 C32 2.0401(18) . y
Fe1 C33 2.0366(18) . y
Fe1 C34 2.0438(17) . y
Fe1 C35 2.0561(18) . y
Fe1 C30 2.0518(17) . y
Fe1 C26 2.0526(16) . y
Fe1 C27 2.0414(17) . y
Fe1 C28 2.0393(17) . y
Fe1 C29 2.0503(17) . y
O1 C5 1.224(2) . ?
O2 C11 1.375(2) . ?
O2 C1 1.373(2) . ?
O1S C2S 1.216(2) . ?
N2 C9 1.345(2) . ?
N2 C10 1.328(2) . ?
N1 C10 1.331(2) . ?
N1 C11 1.337(2) . ?
C31 H31 1.0000 . ?
C31 C32 1.425(3) . ?
C31 C35 1.422(3) . ?
C32 H32 1.0000 . ?
C32 C33 1.421(3) . ?
C33 H33 1.0000 . ?
C33 C34 1.414(3) . ?
C34 H34 1.0000 . ?
C34 C35 1.420(2) . ?
C35 H35 1.0000 . ?
C30 H30 1.0000 . ?
C30 C26 1.430(2) . ?
C30 C29 1.425(2) . ?
C26 C27 1.433(2) . ?
C26 C22 1.480(2) . ?
C27 H27 1.0000 . ?
C27 C28 1.425(2) . ?
C28 H28 1.0000 . ?
C28 C29 1.420(3) . ?
C29 H29 1.0000 . ?
C22 C21 1.394(2) . ?
C22 C23 1.394(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.395(2) . ?
C20 N3 1.415(2) . ?
C20 C25 1.400(2) . ?
N3 H3 0.8799(10) . ?
N3 C9 1.367(2) . ?
C9 C8 1.415(2) . ?
C10 H10 0.9500 . ?
C11 C8 1.376(2) . ?
C8 C7 1.518(2) . ?
C7 H7 1.0000 . ?
C7 C12 1.530(2) . ?
C7 C6 1.513(2) . ?
C12 C17 1.397(2) . ?
C12 C13 1.391(2) . ?
C17 C16 1.388(3) . ?
C17 F1 1.287(16) . ?
C17 H17 0.9500 . ?
C16 H16 0.9500 . ?
C16 C15 1.384(3) . ?
C15 H15 0.9500 . ?
C15 C14 1.387(3) . ?
C14 H14 0.9500 . ?
C14 C13 1.378(2) . ?
C13 F1A 1.359(2) . ?
C13 H13 0.9500 . ?
C6 C1 1.339(2) . ?
C6 C5 1.467(2) . ?
C1 C2 1.489(2) . ?
C2 H2a 0.9900 . ?
C2 H2b 0.9900 . ?
C2 C3 1.536(2) . ?
C3 C18 1.534(2) . ?
C3 C4 1.534(2) . ?
C3 C19 1.534(2) . ?
C18 H18a 0.9800 . ?
C18 H18b 0.9800 . ?
C18 H18c 0.9800 . ?
C4 H4a 0.9900 . ?
C4 H4b 0.9900 . ?
C4 C5 1.514(2) . ?
C19 H19a 0.9800 . ?
C19 H19b 0.9800 . ?
C19 H19c 0.9800 . ?
C25 H25 0.9500 . ?
C25 C24 1.387(2) . ?
C24 H24 0.9500 . ?
C24 C23 1.385(2) . ?
C23 H23 0.9500 . ?
C1S C2S 1.490(3) . ?
C1S H1Sa 0.9800 . ?
C1S H1Sb 0.9800 . ?
C1S H1Sc 0.9800 . ?
C2S C3S 1.503(3) . ?
C3S H3Sa 0.9800 . ?
C3S H3Sb 0.9800 . ?
C3S H3Sc 0.9800 . ?
O1t C2t 1.22(3) . ?
C2t C1t 1.46(3) . ?
C2t C3t 1.47(3) . ?
C1t H1ta 0.9800 . ?
C1t H1tb 0.9800 . ?
C1t H1tc 0.9800 . ?
C3t H3ta 0.9800 . ?
C3t H3tb 0.9800 . ?
C3t H3tc 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
C32 Fe1 C31 40.79(8) . . y
C33 Fe1 C31 68.61(7) . . y
C33 Fe1 C32 40.81(8) . . y
C34 Fe1 C31 68.31(7) . . y
C34 Fe1 C32 68.33(8) . . y
C34 Fe1 C33 40.54(7) . . y
C35 Fe1 C31 40.55(8) . . y
C35 Fe1 C32 68.32(8) . . y
C35 Fe1 C33 68.31(7) . . y
C35 Fe1 C34 40.52(7) . . y
C30 Fe1 C31 123.43(7) . . y
C30 Fe1 C32 158.12(7) . . y
C30 Fe1 C33 160.51(7) . . y
C30 Fe1 C34 125.36(7) . . y
C30 Fe1 C35 109.75(7) . . y
C26 Fe1 C31 108.75(7) . . y
C26 Fe1 C32 121.48(7) . . y
C26 Fe1 C33 156.01(8) . . y
C26 Fe1 C34 162.57(7) . . y
C26 Fe1 C35 126.18(7) . . y
C26 Fe1 C30 40.77(7) . . y
C27 Fe1 C31 124.49(7) . . y
C27 Fe1 C32 106.29(8) . . y
C27 Fe1 C33 119.45(7) . . y
C27 Fe1 C34 155.02(7) . . y
C27 Fe1 C35 162.23(7) . . y
C27 Fe1 C30 68.56(7) . . y
C27 Fe1 C26 40.98(7) . . y
C28 Fe1 C31 160.19(8) . . y
C28 Fe1 C32 122.41(8) . . y
C28 Fe1 C33 105.14(7) . . y
C28 Fe1 C34 119.92(7) . . y
C28 Fe1 C35 156.41(7) . . y
C28 Fe1 C30 68.48(7) . . y
C28 Fe1 C26 68.89(7) . . y
C28 Fe1 C27 40.87(7) . . y
C29 Fe1 C31 158.45(8) . . y
C29 Fe1 C32 159.19(8) . . y
C29 Fe1 C33 122.74(7) . . y
C29 Fe1 C34 107.37(7) . . y
C29 Fe1 C35 122.52(7) . . y
C29 Fe1 C30 40.65(6) . . y
C29 Fe1 C26 68.68(7) . . y
C29 Fe1 C27 68.54(7) . . y
C29 Fe1 C28 40.63(7) . . y
C1 O2 C11 117.74(12) . . ?
C10 N2 C9 116.14(14) . . ?
C11 N1 C10 113.25(14) . . ?
H31 C31 Fe1 126.09(5) . . ?
C32 C31 Fe1 69.33(10) . . ?
C32 C31 H31 126.09(11) . . ?
C35 C31 Fe1 70.05(10) . . ?
C35 C31 H31 126.09(11) . . ?
C35 C31 C32 107.81(16) . . ?
C31 C32 Fe1 69.88(10) . . ?
H32 C32 Fe1 126.02(6) . . ?
H32 C32 C31 126.02(11) . . ?
C33 C32 Fe1 69.46(10) . . ?
C33 C32 C31 107.96(17) . . ?
C33 C32 H32 126.02(11) . . ?
C32 C33 Fe1 69.73(10) . . ?
H33 C33 Fe1 126.01(5) . . ?
H33 C33 C32 126.01(11) . . ?
C34 C33 Fe1 70.00(10) . . ?
C34 C33 C32 107.98(16) . . ?
C34 C33 H33 126.01(11) . . ?
C33 C34 Fe1 69.46(10) . . ?
H34 C34 Fe1 125.81(5) . . ?
H34 C34 C33 125.81(11) . . ?
C35 C34 Fe1 70.20(10) . . ?
C35 C34 C33 108.38(17) . . ?
C35 C34 H34 125.81(11) . . ?
C31 C35 Fe1 69.40(10) . . ?
C34 C35 Fe1 69.28(10) . . ?
C34 C35 C31 107.86(16) . . ?
H35 C35 Fe1 126.06(5) . . ?
H35 C35 C31 126.06(11) . . ?
H35 C35 C34 126.06(11) . . ?
H30 C30 Fe1 125.82(5) . . ?
C26 C30 Fe1 69.64(9) . . ?
C26 C30 H30 125.82(10) . . ?
C29 C30 Fe1 69.62(10) . . ?
C29 C30 H30 125.82(10) . . ?
C29 C30 C26 108.35(15) . . ?
C30 C26 Fe1 69.59(9) . . ?
C27 C26 Fe1 69.09(9) . . ?
C27 C26 C30 107.28(15) . . ?
C22 C26 Fe1 127.21(12) . . ?
C22 C26 C30 126.59(15) . . ?
C22 C26 C27 126.12(15) . . ?
C26 C27 Fe1 69.93(10) . . ?
H27 C27 Fe1 125.92(5) . . ?
H27 C27 C26 125.92(10) . . ?
C28 C27 Fe1 69.49(10) . . ?
C28 C27 C26 108.16(15) . . ?
C28 C27 H27 125.92(10) . . ?
C27 C28 Fe1 69.64(10) . . ?
H28 C28 Fe1 125.91(5) . . ?
H28 C28 C27 125.91(10) . . ?
C29 C28 Fe1 70.10(10) . . ?
C29 C28 C27 108.18(15) . . ?
C29 C28 H28 125.91(10) . . ?
C30 C29 Fe1 69.73(9) . . ?
C28 C29 Fe1 69.27(10) . . ?
C28 C29 C30 108.03(15) . . ?
H29 C29 Fe1 125.98(5) . . ?
H29 C29 C30 125.98(10) . . ?
H29 C29 C28 125.98(10) . . ?
C21 C22 C26 120.14(15) . . ?
C23 C22 C26 120.82(15) . . ?
C23 C22 C21 119.03(15) . . ?
H21 C21 C22 119.39(10) . . ?
C20 C21 C22 121.22(15) . . ?
C20 C21 H21 119.39(10) . . ?
N3 C20 C21 115.82(14) . . ?
C25 C20 C21 119.43(15) . . ?
C25 C20 N3 124.70(15) . . ?
H3 N3 C20 112.9(12) . . ?
C9 N3 C20 129.94(14) . . ?
C9 N3 H3 117.2(12) . . ?
N3 C9 N2 118.70(15) . . ?
C8 C9 N2 121.68(15) . . ?
C8 C9 N3 119.62(14) . . ?
N1 C10 N2 128.48(15) . . ?
H10 C10 N2 115.76(9) . . ?
H10 C10 N1 115.76(9) . . ?
N1 C11 O2 111.57(14) . . ?
C8 C11 O2 122.44(15) . . ?
C8 C11 N1 125.99(16) . . ?
C11 C8 C9 114.39(15) . . ?
C7 C8 C9 124.41(14) . . ?
C7 C8 C11 121.17(15) . . ?
H7 C7 C8 107.98(9) . . ?
C12 C7 C8 112.80(13) . . ?
C12 C7 H7 107.98(9) . . ?
C6 C7 C8 108.41(13) . . ?
C6 C7 H7 107.98(9) . . ?
C6 C7 C12 111.53(13) . . ?
C17 C12 C7 121.67(15) . . ?
C13 C12 C7 122.62(15) . . ?
C13 C12 C17 115.69(16) . . ?
C16 C17 C12 121.79(17) . . ?
F1 C17 C12 117.6(7) . . ?
F1 C17 C16 119.1(7) . . ?
H17 C17 C12 119.10(10) . . ?
H17 C17 C16 119.10(11) . . ?
H17 C17 F1 12.7(7) . . ?
H16 C16 C17 119.90(11) . . ?
C15 C16 C17 120.20(17) . . ?
C15 C16 H16 119.90(11) . . ?
H15 C15 C16 120.14(11) . . ?
C14 C15 C16 119.72(17) . . ?
C14 C15 H15 120.14(11) . . ?
H14 C14 C15 120.70(11) . . ?
C13 C14 C15 118.59(17) . . ?
C13 C14 H14 120.70(11) . . ?
C14 C13 C12 124.00(17) . . ?
F1A C13 C12 118.34(15) . . ?
F1A C13 C14 117.64(16) . . ?
H13 C13 C12 118.00(10) . . ?
H13 C13 C14 118.00(11) . . ?
H13 C13 F1A 1.56(9) . . ?
C1 C6 C7 122.48(15) . . ?
C5 C6 C7 118.65(14) . . ?
C5 C6 C1 118.81(15) . . ?
C6 C1 O2 122.99(15) . . ?
C2 C1 O2 111.10(13) . . ?
C2 C1 C6 125.90(15) . . ?
H2a C2 C1 109.20(9) . . ?
H2b C2 C1 109.20(9) . . ?
H2b C2 H2a 107.9 . . ?
C3 C2 C1 112.04(14) . . ?
C3 C2 H2a 109.20(9) . . ?
C3 C2 H2b 109.20(9) . . ?
C18 C3 C2 108.88(14) . . ?
C4 C3 C2 107.69(14) . . ?
C4 C3 C18 109.70(14) . . ?
C19 C3 C2 110.12(14) . . ?
C19 C3 C18 109.73(14) . . ?
C19 C3 C4 110.69(14) . . ?
H18a C18 C3 109.5 . . ?
H18b C18 C3 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 C3 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?
H4a C4 C3 108.73(9) . . ?
H4b C4 C3 108.73(9) . . ?
H4b C4 H4a 107.6 . . ?
C5 C4 C3 114.11(14) . . ?
C5 C4 H4a 108.73(9) . . ?
C5 C4 H4b 108.73(9) . . ?
C6 C5 O1 120.88(15) . . ?
C4 C5 O1 121.64(15) . . ?
C4 C5 C6 117.36(14) . . ?
H19a C19 C3 109.5 . . ?
H19b C19 C3 109.5 . . ?
H19b C19 H19a 109.5 . . ?
H19c C19 C3 109.5 . . ?
H19c C19 H19a 109.5 . . ?
H19c C19 H19b 109.5 . . ?
H25 C25 C20 120.56(10) . . ?
C24 C25 C20 118.87(15) . . ?
C24 C25 H25 120.56(10) . . ?
H24 C24 C25 119.09(10) . . ?
C23 C24 C25 121.82(15) . . ?
C23 C24 H24 119.09(10) . . ?
C24 C23 C22 119.62(16) . . ?
H23 C23 C22 120.19(10) . . ?
H23 C23 C24 120.19(10) . . ?
H1Sa C1S C2S 109.5 . . ?
H1Sb C1S C2S 109.5 . . ?
H1Sb C1S H1Sa 109.5 . . ?
H1Sc C1S C2S 109.5 . . ?
H1Sc C1S H1Sa 109.5 . . ?
H1Sc C1S H1Sb 109.5 . . ?
C1S C2S O1S 121.8(3) . . ?
C3S C2S O1S 121.4(2) . . ?
C3S C2S C1S 116.8(3) . . ?
H3Sa C3S C2S 109.5 . . ?
H3Sb C3S C2S 109.5 . . ?
H3Sb C3S H3Sa 109.5 . . ?
H3Sc C3S C2S 109.5 . . ?
H3Sc C3S H3Sa 109.5 . . ?
H3Sc C3S H3Sb 109.5 . . ?
C1t C2t O1t 120(4) . . ?
C3t C2t O1t 114(3) . . ?
C3t C2t C1t 124(4) . . ?
H1ta C1t C2t 109.5 . . ?
H1tb C1t C2t 109.5 . . ?
H1tb C1t H1ta 109.5 . . ?
H1tc C1t C2t 109.5 . . ?
H1tc C1t H1ta 109.5 . . ?
H1tc C1t H1tb 109.5 . . ?
H3ta C3t C2t 109.5 . . ?
H3tb C3t C2t 109.5 . . ?
H3tb C3t H3ta 109.5 . . ?
H3tc C3t C2t 109.5 . . ?
H3tc C3t H3ta 109.5 . . ?
H3tc C3t H3tb 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C25 H25 N2 0.9500 2.262(2) 2.875(2) 121.57(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
Fe1 C31 C32 C33 59.24(11) . . . . ?
Fe1 C31 C35 C34 -58.78(11) . . . . ?
Fe1 C32 C31 C35 -59.72(11) . . . . ?
Fe1 C32 C33 C34 59.79(11) . . . . ?
Fe1 C33 C32 C31 -59.50(11) . . . . ?
Fe1 C33 C34 C35 59.62(11) . . . . ?
Fe1 C34 C33 C32 -59.62(11) . . . . ?
Fe1 C34 C35 C31 58.86(11) . . . . ?
Fe1 C35 C31 C32 59.26(11) . . . . ?
Fe1 C35 C34 C33 -59.16(11) . . . . ?
Fe1 C30 C26 C27 -59.03(10) . . . . ?
Fe1 C30 C26 C22 121.83(9) . . . . ?
Fe1 C30 C29 C28 58.87(11) . . . . ?
Fe1 C26 C30 C29 59.04(10) . . . . ?
Fe1 C26 C27 C28 -59.17(11) . . . . ?
Fe1 C26 C22 C21 -56.10(16) . . . . ?
Fe1 C26 C22 C23 124.43(15) . . . . ?
Fe1 C27 C26 C30 59.34(10) . . . . ?
Fe1 C27 C26 C22 -121.51(9) . . . . ?
Fe1 C27 C28 C29 -59.73(11) . . . . ?
Fe1 C28 C27 C26 59.45(10) . . . . ?
Fe1 C28 C29 C30 -59.16(11) . . . . ?
Fe1 C29 C30 C26 -59.05(10) . . . . ?
Fe1 C29 C28 C27 59.45(11) . . . . ?
O1 C5 C6 C7 -3.68(19) . . . . ?
O1 C5 C6 C1 173.57(16) . . . . ?
O1 C5 C4 C3 154.07(16) . . . . ?
O2 C11 N1 C10 -179.00(14) . . . . ?
O2 C11 C8 C9 177.84(16) . . . . ?
O2 C11 C8 C7 -3.84(19) . . . . ?
O2 C1 C6 C7 5.85(19) . . . . ?
O2 C1 C6 C5 -171.29(15) . . . . ?
O2 C1 C2 C3 -161.25(13) . . . . ?
N2 C9 N3 C20 15.0(2) . . . . ?
N2 C9 C8 C11 1.15(18) . . . . ?
N2 C9 C8 C7 -177.11(15) . . . . ?
N2 C10 N1 C11 1.5(2) . . . . ?
N1 C11 C8 C9 -2.5(2) . . . . ?
N1 C11 C8 C7 175.81(16) . . . . ?
C31 C32 C33 C34 0.30(16) . . . . ?
C31 C35 C34 C33 -0.30(16) . . . . ?
C32 C33 C34 C35 0.00(16) . . . . ?
C30 C26 C27 C28 0.17(15) . . . . ?
C30 C26 C22 C21 -147.15(17) . . . . ?
C30 C26 C22 C23 33.4(2) . . . . ?
C30 C29 C28 C27 0.29(15) . . . . ?
C26 C27 C28 C29 -0.29(15) . . . . ?
C26 C22 C21 C20 179.86(15) . . . . ?
C26 C22 C23 C24 179.33(16) . . . . ?
C22 C21 C20 N3 -176.77(16) . . . . ?
C22 C21 C20 C25 0.89(19) . . . . ?
C22 C23 C24 C25 0.72(19) . . . . ?
C21 C20 N3 C9 176.70(14) . . . . ?
C21 C20 C25 C24 -0.31(19) . . . . ?
C20 N3 C9 C8 -164.79(17) . . . . ?
C20 C25 C24 C23 -0.49(19) . . . . ?
N3 C9 C8 C11 -179.03(16) . . . . ?
N3 C9 C8 C7 2.71(19) . . . . ?
C9 C8 C7 C12 73.57(17) . . . . ?
C9 C8 C7 C6 -162.42(17) . . . . ?
C11 C8 C7 C12 -104.59(16) . . . . ?
C11 C8 C7 C6 19.43(17) . . . . ?
C8 C7 C12 C17 -116.94(14) . . . . ?
C8 C7 C12 C13 64.46(16) . . . . ?
C8 C7 C6 C1 -20.65(16) . . . . ?
C8 C7 C6 C5 156.50(13) . . . . ?
C7 C12 C17 C16 -178.66(15) . . . . ?
C7 C12 C17 F1 15.7(8) . . . . ?
C7 C12 C13 C14 178.19(15) . . . . ?
C7 C12 C13 F1A -3.54(17) . . . . ?
C7 C6 C1 C2 -175.17(15) . . . . ?
C7 C6 C5 C4 -179.73(14) . . . . ?
C12 C17 C16 C15 0.6(2) . . . . ?
C12 C13 C14 C15 0.3(2) . . . . ?
C17 C16 C15 C14 -0.8(2) . . . . ?
C16 C15 C14 C13 0.3(2) . . . . ?
C15 C14 C13 F1A -177.97(15) . . . . ?
C6 C1 C2 C3 19.66(19) . . . . ?
C6 C5 C4 C3 -29.91(16) . . . . ?
C1 C2 C3 C18 -167.31(15) . . . . ?
C1 C2 C3 C4 -48.43(15) . . . . ?
C1 C2 C3 C19 72.35(15) . . . . ?
C2 C3 C4 C5 54.42(15) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
N3 H3 1 0.8800 0.0010 0.0001

loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_id
O1S C1S 1 4
O1S C2S 1 1
O1S C3S 1 5
C1S C2S 1 2
C1S C3S 1 6
C2S C3S 1 3
O1t C2t 1 1
O1t C1t 1 4
O1t C3t 1 5
C2t C3t 1 3
C1t C2t 1 2
C1t C3t 1 6

loop_
_restr_equal_distance_class_class_id
_restr_equal_distance_class_target_weight_param
_restr_equal_distance_class_average
_restr_equal_distance_class_esd
_restr_equal_distance_class_diff_max
1 0.0200 1.2183 0.0023 0.0023
2 0.0200 1.4751 0.0149 0.0149
3 0.0200 1.4875 0.0159 0.0159
4 0.0400 2.3481 0.0197 0.0197
5 0.0400 2.3204 0.0554 0.0554
6 0.0400 2.5719 0.0223 0.0223

loop_
_restr_U_similar_atom_site_label_1
_restr_U_similar_atom_site_label_2
_restr_U_similar_weight_param
O1t C2t 0.0020
C2t C1t 0.0010
C2t C3t 0.0010

