# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

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

data_4
_database_code_depnum_ccdc_archive 'CCDC 2452448'
loop_
_audit_author_name
_audit_author_address
'Sizwe Zamisa'
;University of KwaZulu Natal
South Africa
;
_audit_update_record             
;
2025-05-19 deposited with the CCDC.	2025-09-12 downloaded from the CCDC.
;
_audit_creation_date             2025-04-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_chemical_formula_moiety         '2(C25 H36 N2 O), C H2 Cl2'
_chemical_formula_sum            'C51 H74 Cl2 N4 O2'
_chemical_formula_weight         846.087
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'
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                   12.6939(3)
_cell_length_b                   13.0267(3)
_cell_length_c                   18.5039(5)
_cell_angle_alpha                84.192(1)
_cell_angle_beta                 76.836(1)
_cell_angle_gamma                61.861(1)
_cell_volume                     2627.18(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296.15
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6590
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0879 before and 0.0407 after correction.
The Ratio of minimum to maximum transmission is 0.8837.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.070
_exptl_crystal_description       block
_exptl_crystal_F_000             917.046
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.9744
_diffrn_reflns_Laue_measured_fraction_max 0.9696
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20842
_diffrn_reflns_point_group_measured_fraction_full 0.9744
_diffrn_reflns_point_group_measured_fraction_max 0.9696
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         1.86
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9744
_diffrn_measured_fraction_theta_max 0.9696
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              16
_reflns_limit_k_min              -15
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                6418
_reflns_number_total             10046
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.6476
_refine_diff_density_min         -0.7286
_refine_diff_density_rms         0.0654
_refine_ls_d_res_high            0.8100
_refine_ls_d_res_low             10.9554
_refine_ls_goodness_of_fit_ref   1.0554
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    115
_refine_ls_number_parameters     549
_refine_ls_number_reflns         10046
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1136
_refine_ls_R_factor_gt           0.0782
_refine_ls_restrained_S_all      1.0554
_refine_ls_shift/su_max          -0.0130
_refine_ls_shift/su_mean         0.0012
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1455P)²+0.7101P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2280
_refine_ls_wR_factor_ref         0.2677
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C10(H10), C20(H20), C35(H35), C7(H7), C23(H23), C45(H45), C32(H32), C48(H48)
1.b Secondary CH2 refined with riding coordinates:
 C51(H51a,H51b)
1.c Aromatic/amide H refined with riding coordinates:
 N4(H4a), C13(H13), C38(H38), C3(H3), C18(H18), C5(H5), C4(H4), C28(H28),
 C17(H17), C29(H29), C16(H16), C43(H43), C30(H30), C41(H41), C42(H42)
1.d Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c), C37(H37a,H37b,H37c), C9(H9a,H9b,H9c), C8(H8a,H8b,H8c),
 C12(H12a,H12b,H12c), C11(H11a,H11b,H11c), C22(H22a,H22b,H22c), C36(H36a,H36b,
 H36c), C49(H49a,H49b,H49c), C50(H50a,H50b,H50c), C24(H24a,H24b,H24c), C33(H33a,
 H33b,H33c), C47(H47a,H47b,H47c), C25(H25a,H25b,H25c), C46(H46a,H46b,H46c),
 C34(H34a,H34b,H34c)
1.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
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
O2 O 0.56655(16) 0.71720(14) 0.19567(10) 0.0543(4) Uani 1.000000 .
H2 H 0.539(3) 0.7356(4) 0.23963(13) 0.0814(7) Uiso 1.000000 GR
O1 O 0.4644(2) 0.80175(17) 0.32546(10) 0.0649(5) Uani 1.000000 .
N1 N 0.32543(18) 0.84709(17) 0.18606(11) 0.0480(5) Uani 1.000000 .
Cl1 Cl 0.98105(19) 0.5534(2) 0.15937(15) 0.1967(9) Uani 1.000000 .
N2 N 0.52602(17) 0.81591(17) 0.15245(11) 0.0464(5) Uani 1.000000 .
N4 N 0.35666(19) 0.67164(18) 0.30572(12) 0.0522(5) Uani 1.000000 .
H4a H 0.35234(19) 0.72650(18) 0.27459(12) 0.0626(6) Uiso 1.000000 R
N3 N 0.4588(2) 0.71900(18) 0.37486(11) 0.0532(5) Uani 1.000000 .
Cl2 Cl 0.9087(2) 0.3979(2) 0.1123(2) 0.2577(16) Uani 1.000000 .
C13 C 0.4084(2) 0.8735(2) 0.14882(13) 0.0459(5) Uani 1.000000 .
H13 H 0.3844(2) 0.9370(2) 0.11725(13) 0.0551(6) Uiso 1.000000 R
C38 C 0.4057(2) 0.6587(2) 0.36368(14) 0.0521(6) Uani 1.000000 .
H38 H 0.4023(2) 0.6034(2) 0.39878(14) 0.0625(7) Uiso 1.000000 R
C1 C 0.2014(2) 0.9232(2) 0.17823(14) 0.0492(6) Uani 1.000000 .
C14 C 0.6200(2) 0.8386(2) 0.10717(14) 0.0500(6) Uani 1.000000 .
C26 C 0.3105(2) 0.5944(2) 0.29448(14) 0.0523(6) Uani 1.000000 .
C39 C 0.5095(3) 0.7064(2) 0.43933(14) 0.0584(7) Uani 1.000000 .
C19 C 0.6584(2) 0.8061(2) 0.03213(15) 0.0581(6) Uani 1.000000 .
C2 C 0.1525(2) 0.8947(2) 0.12715(15) 0.0562(6) Uani 1.000000 .
C27 C 0.3892(3) 0.4937(2) 0.25060(16) 0.0625(7) Uani 1.000000 .
C6 C 0.1301(3) 1.0229(2) 0.22380(16) 0.0603(7) Uani 1.000000 .
C15 C 0.6736(3) 0.8893(3) 0.14084(17) 0.0624(7) Uani 1.000000 .
C10 C 0.2248(3) 0.7846(3) 0.0801(2) 0.0757(9) Uani 1.000000 .
H10 H 0.3102(3) 0.7508(3) 0.0846(2) 0.0909(10) Uiso 1.000000 R
C40 C 0.6218(3) 0.6099(3) 0.44377(17) 0.0721(8) Uani 1.000000 .
C44 C 0.4441(3) 0.7930(3) 0.49408(17) 0.0724(8) Uani 1.000000 .
C31 C 0.1889(3) 0.6223(3) 0.32400(18) 0.0704(8) Uani 1.000000 .
C20 C 0.6020(3) 0.7489(3) -0.00356(16) 0.0674(7) Uani 1.000000 .
H20 H 0.5467(3) 0.7318(3) 0.03611(16) 0.0809(9) Uiso 1.000000 R
C3 C 0.0328(3) 0.9701(3) 0.12077(19) 0.0708(8) Uani 1.000000 .
H3 H -0.0005(3) 0.9528(3) 0.08678(19) 0.0850(9) Uiso 1.000000 R
C18 C 0.7527(3) 0.8279(3) -0.00949(19) 0.0787(9) Uani 1.000000 .
H18 H 0.7798(3) 0.8083(3) -0.05967(19) 0.0944(11) Uiso 1.000000 R
C35 C 0.5202(3) 0.4651(3) 0.21539(19) 0.0751(8) Uani 1.000000 .
H35 H 0.5407(3) 0.5160(3) 0.23848(19) 0.0901(10) Uiso 1.000000 R
C7 C 0.1796(3) 1.0526(3) 0.28159(18) 0.0720(8) Uani 1.000000 .
H7 H 0.2537(3) 0.9823(3) 0.28869(18) 0.0864(10) Uiso 1.000000 R
C23 C 0.6317(3) 0.9226(3) 0.22228(18) 0.0739(9) Uani 1.000000 .
H23 H 0.5578(3) 0.9136(3) 0.24078(18) 0.0887(10) Uiso 1.000000 R
C5 C 0.0109(3) 1.0947(3) 0.2146(2) 0.0793(9) Uani 1.000000 .
H5 H -0.0376(3) 1.1616(3) 0.2436(2) 0.0952(11) Uiso 1.000000 R
C4 C -0.0369(3) 1.0688(3) 0.1632(2) 0.0811(9) Uani 1.000000 .
H4 H -0.1163(3) 1.1183(3) 0.1575(2) 0.0974(11) Uiso 1.000000 R
C45 C 0.3275(4) 0.9001(3) 0.4853(2) 0.0830(9) Uani 1.000000 .
H45 H 0.3115(4) 0.8922(3) 0.4373(2) 0.0996(11) Uiso 1.000000 R
C28 C 0.3418(4) 0.4208(3) 0.2398(2) 0.0792(9) Uani 1.000000 .
H28 H 0.3918(4) 0.3536(3) 0.2113(2) 0.0950(11) Uiso 1.000000 R
C17 C 0.8057(3) 0.8772(4) 0.0221(2) 0.0944(12) Uani 1.000000 .
H17 H 0.8680(3) 0.8911(4) -0.0067(2) 0.1133(14) Uiso 1.000000 R
C29 C 0.2235(4) 0.4457(3) 0.2700(2) 0.0894(11) Uani 1.000000 .
H29 H 0.1946(4) 0.3948(3) 0.2624(2) 0.1073(13) Uiso 1.000000 R
C16 C 0.7673(3) 0.9063(3) 0.0962(2) 0.0859(10) Uani 1.000000 .
H16 H 0.8054(3) 0.9385(3) 0.1169(2) 0.1030(12) Uiso 1.000000 R
C32 C 0.1016(3) 0.7372(4) 0.3657(3) 0.1032(13) Uani 1.000000 .
H32 H 0.1489(3) 0.7779(4) 0.3681(3) 0.1239(16) Uiso 1.000000 R
C43 C 0.4939(5) 0.7776(4) 0.5568(2) 0.1014(13) Uani 1.000000 .
H43 H 0.4539(5) 0.8337(4) 0.5943(2) 0.1216(15) Uiso 1.000000 R
C48 C 0.6967(3) 0.5210(3) 0.3819(2) 0.0900(11) Uani 1.000000 .
H48 H 0.6582(3) 0.5503(3) 0.3388(2) 0.1080(13) Uiso 1.000000 R
C30 C 0.1471(4) 0.5447(4) 0.3114(2) 0.0875(10) Uani 1.000000 .
H30 H 0.0667(4) 0.5608(4) 0.3313(2) 0.1050(12) Uiso 1.000000 R
C41 C 0.6646(4) 0.5995(4) 0.5086(2) 0.0961(12) Uani 1.000000 .
H41 H 0.7381(4) 0.5360(4) 0.5142(2) 0.1154(14) Uiso 1.000000 R
C42 C 0.6005(5) 0.6812(5) 0.5638(3) 0.1153(16) Uani 1.000000 .
H42 H 0.6299(5) 0.6710(5) 0.6071(3) 0.1383(19) Uiso 1.000000 R
C21 C 0.5263(4) 0.8318(4) -0.0571(2) 0.1025(13) Uani 1.000000 .
H21a H 0.467(2) 0.9035(11) -0.0318(5) 0.1537(19) Uiso 1.000000 GR
H21b H 0.5789(6) 0.847(2) -0.0980(10) 0.1537(19) Uiso 1.000000 GR
H21c H 0.485(2) 0.7973(13) -0.0752(14) 0.1537(19) Uiso 1.000000 GR
C37 C 0.5316(5) 0.4932(4) 0.1325(2) 0.1136(14) Uani 1.000000 .
H37a H 0.507(3) 0.448(2) 0.1087(4) 0.170(2) Uiso 1.000000 GR
H37b H 0.480(3) 0.5746(8) 0.1262(2) 0.170(2) Uiso 1.000000 GR
H37c H 0.6149(8) 0.474(3) 0.1107(5) 0.170(2) Uiso 1.000000 GR
C9 C 0.0927(4) 1.0837(5) 0.3563(2) 0.1155(15) Uani 1.000000 .
H9a H 0.0231(16) 1.1576(16) 0.3532(6) 0.173(2) Uiso 1.000000 GR
H9b H 0.067(3) 1.0251(17) 0.3704(10) 0.173(2) Uiso 1.000000 GR
H9c H 0.1335(11) 1.088(3) 0.3928(5) 0.173(2) Uiso 1.000000 GR
C8 C 0.2167(6) 1.1460(5) 0.2551(3) 0.1288(18) Uani 1.000000 .
H8a H 0.273(3) 1.1230(17) 0.2083(12) 0.193(3) Uiso 1.000000 GR
H8b H 0.1458(8) 1.2174(10) 0.249(2) 0.193(3) Uiso 1.000000 GR
H8c H 0.254(4) 1.157(3) 0.2908(12) 0.193(3) Uiso 1.000000 GR
C12 C 0.2201(5) 0.8072(4) -0.0019(2) 0.1201(16) Uani 1.000000 .
H12a H 0.1376(8) 0.836(3) -0.0079(3) 0.180(2) Uiso 1.000000 GR
H12b H 0.248(3) 0.864(3) -0.0199(6) 0.180(2) Uiso 1.000000 GR
H12c H 0.271(3) 0.7359(8) -0.0295(4) 0.180(2) Uiso 1.000000 GR
C11 C 0.1789(6) 0.6963(4) 0.1090(3) 0.1237(17) Uani 1.000000 .
H11a H 0.176(4) 0.687(3) 0.1615(5) 0.186(3) Uiso 1.000000 GR
H11b H 0.0988(16) 0.7233(17) 0.099(2) 0.186(3) Uiso 1.000000 GR
H11c H 0.233(2) 0.6229(10) 0.0844(17) 0.186(3) Uiso 1.000000 GR
C22 C 0.6987(5) 0.6330(4) -0.0421(3) 0.1204(16) Uani 1.000000 .
H22a H 0.755(2) 0.6469(6) -0.0810(14) 0.181(2) Uiso 1.000000 GR
H22b H 0.742(2) 0.5807(13) -0.0066(5) 0.181(2) Uiso 1.000000 GR
H22c H 0.6593(6) 0.5991(17) -0.0629(19) 0.181(2) Uiso 1.000000 GR
C36 C 0.6113(4) 0.3414(4) 0.2272(3) 0.1245(17) Uani 1.000000 .
H36a H 0.601(3) 0.3243(12) 0.2792(4) 0.187(3) Uiso 1.000000 GR
H36b H 0.598(2) 0.2894(4) 0.2013(19) 0.187(3) Uiso 1.000000 GR
H36c H 0.6925(4) 0.3317(10) 0.208(2) 0.187(3) Uiso 1.000000 GR
C49 C 0.6965(6) 0.4049(4) 0.4035(3) 0.1296(17) Uani 1.000000 .
H49a H 0.731(4) 0.3757(19) 0.4470(15) 0.194(3) Uiso 1.000000 GR
H49b H 0.6143(7) 0.4159(9) 0.414(2) 0.194(3) Uiso 1.000000 GR
H49c H 0.745(3) 0.3501(12) 0.3634(10) 0.194(3) Uiso 1.000000 GR
C50 C 0.8277(4) 0.5057(6) 0.3587(3) 0.143(2) Uani 1.000000 .
H50a H 0.8255(5) 0.5808(6) 0.354(3) 0.215(3) Uiso 1.000000 GR
H50b H 0.8736(14) 0.461(4) 0.3955(14) 0.215(3) Uiso 1.000000 GR
H50c H 0.8659(16) 0.466(4) 0.3117(14) 0.215(3) Uiso 1.000000 GR
C24 C 0.5976(7) 1.0484(5) 0.2353(3) 0.146(2) Uani 1.000000 .
H24a H 0.6683(12) 1.0604(12) 0.218(3) 0.219(3) Uiso 1.000000 GR
H24b H 0.535(3) 1.0984(5) 0.209(2) 0.219(3) Uiso 1.000000 GR
H24c H 0.568(5) 1.0662(14) 0.2874(5) 0.219(3) Uiso 1.000000 GR
C33 C 0.0012(5) 0.8149(5) 0.3269(3) 0.1315(18) Uani 1.000000 .
H33a H 0.0348(6) 0.821(3) 0.2755(6) 0.197(3) Uiso 1.000000 GR
H33b H -0.055(2) 0.783(2) 0.331(2) 0.197(3) Uiso 1.000000 GR
H33c H -0.041(3) 0.8909(11) 0.3493(16) 0.197(3) Uiso 1.000000 GR
C47 C 0.3417(7) 1.0088(5) 0.4814(5) 0.160(3) Uani 1.000000 .
H47a H 0.350(5) 1.024(3) 0.5290(9) 0.240(4) Uiso 1.000000 GR
H47b H 0.413(3) 0.9985(19) 0.445(2) 0.240(4) Uiso 1.000000 GR
H47c H 0.271(2) 1.0732(11) 0.468(3) 0.240(4) Uiso 1.000000 GR
C51 C 0.8816(7) 0.5438(6) 0.1216(5) 0.224(5) Uani 1.000000 .
H51a H 0.8007(7) 0.5879(6) 0.1515(5) 0.268(6) Uiso 1.000000 R
H51b H 0.8830(7) 0.5791(6) 0.0728(5) 0.268(6) Uiso 1.000000 R
C25 C 0.7235(6) 0.8432(6) 0.2663(3) 0.149(2) Uani 1.000000 .
H25a H 0.748(4) 0.7638(6) 0.255(2) 0.223(3) Uiso 1.000000 GR
H25b H 0.793(2) 0.857(3) 0.254(2) 0.223(3) Uiso 1.000000 GR
H25c H 0.6883(16) 0.858(3) 0.3183(3) 0.223(3) Uiso 1.000000 GR
C46 C 0.2182(6) 0.9086(6) 0.5437(4) 0.171(3) Uani 1.000000 .
H46a H 0.203(4) 0.845(3) 0.538(2) 0.256(4) Uiso 1.000000 GR
H46b H 0.235(2) 0.906(6) 0.5922(4) 0.256(4) Uiso 1.000000 GR
H46c H 0.1479(15) 0.981(3) 0.538(2) 0.256(4) Uiso 1.000000 GR
C34 C 0.0490(8) 0.7178(7) 0.4440(3) 0.242(5) Uani 1.000000 .
H34a H 0.007(8) 0.673(8) 0.4436(4) 0.363(8) Uiso 1.000000 GR
H34b H 0.1137(14) 0.676(8) 0.4707(17) 0.363(8) Uiso 1.000000 GR
H34c H -0.007(7) 0.7915(7) 0.4678(19) 0.363(8) Uiso 1.000000 GR


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
O2 H2 0.8200 . ?
O2 N2 1.383(2) . ?
O1 N3 1.358(3) . ?
N1 C13 1.290(3) . ?
N1 C1 1.444(3) . ?
Cl1 C51 1.634(8) . ?
N2 C13 1.333(3) . ?
N2 C14 1.429(3) . ?
N4 H4a 0.8600 . ?
N4 C38 1.317(3) . ?
N4 C26 1.433(3) . ?
N3 C38 1.309(3) . ?
N3 C39 1.440(3) . ?
Cl2 C51 1.784(9) . ?
C13 H13 0.9300 . ?
C38 H38 0.9300 . ?
C1 C2 1.404(4) . ?
C1 C6 1.408(4) . ?
C14 C19 1.400(4) . ?
C14 C15 1.410(4) . ?
C26 C27 1.410(4) . ?
C26 C31 1.393(4) . ?
C39 C40 1.401(4) . ?
C39 C44 1.398(4) . ?
C19 C20 1.524(4) . ?
C19 C18 1.400(4) . ?
C2 C10 1.518(4) . ?
C2 C3 1.391(4) . ?
C27 C35 1.516(4) . ?
C27 C28 1.392(4) . ?
C6 C7 1.518(4) . ?
C6 C5 1.395(4) . ?
C15 C23 1.514(4) . ?
C15 C16 1.382(4) . ?
C10 H10 0.9800 . ?
C10 C12 1.526(5) . ?
C10 C11 1.520(6) . ?
C40 C48 1.513(5) . ?
C40 C41 1.395(5) . ?
C44 C45 1.510(5) . ?
C44 C43 1.398(5) . ?
C31 C32 1.531(5) . ?
C31 C30 1.403(5) . ?
C20 H20 0.9800 . ?
C20 C21 1.519(5) . ?
C20 C22 1.538(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.366(5) . ?
C18 H18 0.9300 . ?
C18 C17 1.369(5) . ?
C35 H35 0.9800 . ?
C35 C37 1.530(6) . ?
C35 C36 1.506(5) . ?
C7 H7 0.9800 . ?
C7 C9 1.513(5) . ?
C7 C8 1.504(6) . ?
C23 H23 0.9800 . ?
C23 C24 1.514(6) . ?
C23 C25 1.490(6) . ?
C5 H5 0.9300 . ?
C5 C4 1.381(5) . ?
C4 H4 0.9300 . ?
C45 H45 0.9800 . ?
C45 C47 1.503(6) . ?
C45 C46 1.516(7) . ?
C28 H28 0.9300 . ?
C28 C29 1.367(5) . ?
C17 H17 0.9300 . ?
C17 C16 1.374(6) . ?
C29 H29 0.9300 . ?
C29 C30 1.368(6) . ?
C16 H16 0.9300 . ?
C32 H32 0.9800 . ?
C32 C33 1.489(6) . ?
C32 C34 1.501(8) . ?
C43 H43 0.9300 . ?
C43 C42 1.368(7) . ?
C48 H48 0.9800 . ?
C48 C49 1.525(6) . ?
C48 C50 1.540(7) . ?
C30 H30 0.9300 . ?
C41 H41 0.9300 . ?
C41 C42 1.365(7) . ?
C42 H42 0.9300 . ?
C21 H21a 0.9600 . ?
C21 H21b 0.9600 . ?
C21 H21c 0.9600 . ?
C37 H37a 0.9600 . ?
C37 H37b 0.9600 . ?
C37 H37c 0.9600 . ?
C9 H9a 0.9600 . ?
C9 H9b 0.9600 . ?
C9 H9c 0.9600 . ?
C8 H8a 0.9600 . ?
C8 H8b 0.9600 . ?
C8 H8c 0.9600 . ?
C12 H12a 0.9600 . ?
C12 H12b 0.9600 . ?
C12 H12c 0.9600 . ?
C11 H11a 0.9600 . ?
C11 H11b 0.9600 . ?
C11 H11c 0.9600 . ?
C22 H22a 0.9600 . ?
C22 H22b 0.9600 . ?
C22 H22c 0.9600 . ?
C36 H36a 0.9600 . ?
C36 H36b 0.9600 . ?
C36 H36c 0.9600 . ?
C49 H49a 0.9600 . ?
C49 H49b 0.9600 . ?
C49 H49c 0.9600 . ?
C50 H50a 0.9600 . ?
C50 H50b 0.9600 . ?
C50 H50c 0.9600 . ?
C24 H24a 0.9600 . ?
C24 H24b 0.9600 . ?
C24 H24c 0.9600 . ?
C33 H33a 0.9600 . ?
C33 H33b 0.9600 . ?
C33 H33c 0.9600 . ?
C47 H47a 0.9600 . ?
C47 H47b 0.9600 . ?
C47 H47c 0.9600 . ?
C51 H51a 0.9700 . ?
C51 H51b 0.9700 . ?
C25 H25a 0.9600 . ?
C25 H25b 0.9600 . ?
C25 H25c 0.9600 . ?
C46 H46a 0.9600 . ?
C46 H46b 0.9600 . ?
C46 H46c 0.9600 . ?
C34 H34a 0.9600 . ?
C34 H34b 0.9600 . ?
C34 H34c 0.9600 . ?

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
N2 O2 H2 109.5 . . ?
C1 N1 C13 116.85(19) . . ?
C13 N2 O2 119.55(18) . . ?
C14 N2 O2 115.03(17) . . ?
C14 N2 C13 124.90(19) . . ?
C38 N4 H4a 119.98(14) . . ?
C26 N4 H4a 119.98(12) . . ?
C26 N4 C38 120.0(2) . . ?
C38 N3 O1 119.9(2) . . ?
C39 N3 O1 116.45(19) . . ?
C39 N3 C38 123.6(2) . . ?
N2 C13 N1 124.5(2) . . ?
H13 C13 N1 117.74(13) . . ?
H13 C13 N2 117.74(13) . . ?
N3 C38 N4 123.9(2) . . ?
H38 C38 N4 118.03(14) . . ?
H38 C38 N3 118.03(14) . . ?
C2 C1 N1 119.6(2) . . ?
C6 C1 N1 119.3(2) . . ?
C6 C1 C2 121.1(2) . . ?
C19 C14 N2 119.1(2) . . ?
C15 C14 N2 118.3(2) . . ?
C15 C14 C19 122.6(2) . . ?
C27 C26 N4 118.5(2) . . ?
C31 C26 N4 119.8(2) . . ?
C31 C26 C27 121.6(2) . . ?
C40 C39 N3 119.0(3) . . ?
C44 C39 N3 117.8(3) . . ?
C44 C39 C40 123.3(3) . . ?
C20 C19 C14 122.3(2) . . ?
C18 C19 C14 116.9(3) . . ?
C18 C19 C20 120.7(3) . . ?
C10 C2 C1 122.3(2) . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 C10 119.5(2) . . ?
C35 C27 C26 122.1(2) . . ?
C28 C27 C26 117.4(3) . . ?
C28 C27 C35 120.5(3) . . ?
C7 C6 C1 121.9(2) . . ?
C5 C6 C1 117.8(3) . . ?
C5 C6 C7 120.3(3) . . ?
C23 C15 C14 121.7(2) . . ?
C16 C15 C14 116.9(3) . . ?
C16 C15 C23 121.3(3) . . ?
H10 C10 C2 108.01(15) . . ?
C12 C10 C2 112.8(3) . . ?
C12 C10 H10 108.0(3) . . ?
C11 C10 C2 110.2(3) . . ?
C11 C10 H10 108.0(3) . . ?
C11 C10 C12 109.6(3) . . ?
C48 C40 C39 123.1(3) . . ?
C41 C40 C39 116.6(3) . . ?
C41 C40 C48 120.3(3) . . ?
C45 C44 C39 122.0(3) . . ?
C43 C44 C39 116.7(3) . . ?
C43 C44 C45 121.3(3) . . ?
C32 C31 C26 121.1(3) . . ?
C30 C31 C26 118.1(3) . . ?
C30 C31 C32 120.8(3) . . ?
H20 C20 C19 107.58(15) . . ?
C21 C20 C19 110.7(3) . . ?
C21 C20 H20 107.6(2) . . ?
C22 C20 C19 112.1(3) . . ?
C22 C20 H20 107.6(2) . . ?
C22 C20 C21 111.1(3) . . ?
H3 C3 C2 119.16(18) . . ?
C4 C3 C2 121.7(3) . . ?
C4 C3 H3 119.16(18) . . ?
H18 C18 C19 119.3(2) . . ?
C17 C18 C19 121.4(3) . . ?
C17 C18 H18 119.3(2) . . ?
H35 C35 C27 107.37(15) . . ?
C37 C35 C27 110.1(3) . . ?
C37 C35 H35 107.4(2) . . ?
C36 C35 C27 113.9(3) . . ?
C36 C35 H35 107.4(3) . . ?
C36 C35 C37 110.5(3) . . ?
H7 C7 C6 106.89(15) . . ?
C9 C7 C6 112.8(3) . . ?
C9 C7 H7 106.9(2) . . ?
C8 C7 C6 111.7(3) . . ?
C8 C7 H7 106.9(3) . . ?
C8 C7 C9 111.3(4) . . ?
H23 C23 C15 107.09(15) . . ?
C24 C23 C15 112.8(3) . . ?
C24 C23 H23 107.1(3) . . ?
C25 C23 C15 111.8(4) . . ?
C25 C23 H23 107.1(3) . . ?
C25 C23 C24 110.7(4) . . ?
H5 C5 C6 119.26(19) . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 H5 119.26(19) . . ?
C5 C4 C3 119.8(3) . . ?
H4 C4 C3 120.11(18) . . ?
H4 C4 C5 120.11(19) . . ?
H45 C45 C44 106.61(17) . . ?
C47 C45 C44 111.5(4) . . ?
C47 C45 H45 106.6(3) . . ?
C46 C45 C44 112.6(4) . . ?
C46 C45 H45 106.6(4) . . ?
C46 C45 C47 112.4(5) . . ?
H28 C28 C27 119.2(2) . . ?
C29 C28 C27 121.6(3) . . ?
C29 C28 H28 119.2(2) . . ?
H17 C17 C18 119.9(2) . . ?
C16 C17 C18 120.2(3) . . ?
C16 C17 H17 119.9(2) . . ?
H29 C29 C28 119.7(2) . . ?
C30 C29 C28 120.6(3) . . ?
C30 C29 H29 119.7(2) . . ?
C17 C16 C15 121.9(3) . . ?
H16 C16 C15 119.0(2) . . ?
H16 C16 C17 119.0(2) . . ?
H32 C32 C31 107.46(19) . . ?
C33 C32 C31 112.5(4) . . ?
C33 C32 H32 107.5(3) . . ?
C34 C32 C31 111.9(4) . . ?
C34 C32 H32 107.5(5) . . ?
C34 C32 C33 109.9(4) . . ?
H43 C43 C44 119.5(3) . . ?
C42 C43 C44 120.9(4) . . ?
C42 C43 H43 119.5(2) . . ?
H48 C48 C40 107.62(17) . . ?
C49 C48 C40 111.1(3) . . ?
C49 C48 H48 107.6(3) . . ?
C50 C48 C40 111.5(4) . . ?
C50 C48 H48 107.6(3) . . ?
C50 C48 C49 111.2(4) . . ?
C29 C30 C31 120.7(3) . . ?
H30 C30 C31 119.7(2) . . ?
H30 C30 C29 119.7(2) . . ?
H41 C41 C40 119.4(2) . . ?
C42 C41 C40 121.1(4) . . ?
C42 C41 H41 119.4(2) . . ?
C41 C42 C43 121.2(3) . . ?
H42 C42 C43 119.4(3) . . ?
H42 C42 C41 119.4(2) . . ?
H21a C21 C20 109.5 . . ?
H21b C21 C20 109.5 . . ?
H21b C21 H21a 109.5 . . ?
H21c C21 C20 109.5 . . ?
H21c C21 H21a 109.5 . . ?
H21c C21 H21b 109.5 . . ?
H37a C37 C35 109.5 . . ?
H37b C37 C35 109.5 . . ?
H37b C37 H37a 109.5 . . ?
H37c C37 C35 109.5 . . ?
H37c C37 H37a 109.5 . . ?
H37c C37 H37b 109.5 . . ?
H9a C9 C7 109.5 . . ?
H9b C9 C7 109.5 . . ?
H9b C9 H9a 109.5 . . ?
H9c C9 C7 109.5 . . ?
H9c C9 H9a 109.5 . . ?
H9c C9 H9b 109.5 . . ?
H8a C8 C7 109.5 . . ?
H8b C8 C7 109.5 . . ?
H8b C8 H8a 109.5 . . ?
H8c C8 C7 109.5 . . ?
H8c C8 H8a 109.5 . . ?
H8c C8 H8b 109.5 . . ?
H12a C12 C10 109.5 . . ?
H12b C12 C10 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 C10 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
H11a C11 C10 109.5 . . ?
H11b C11 C10 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 C10 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
H22a C22 C20 109.5 . . ?
H22b C22 C20 109.5 . . ?
H22b C22 H22a 109.5 . . ?
H22c C22 C20 109.5 . . ?
H22c C22 H22a 109.5 . . ?
H22c C22 H22b 109.5 . . ?
H36a C36 C35 109.5 . . ?
H36b C36 C35 109.5 . . ?
H36b C36 H36a 109.5 . . ?
H36c C36 C35 109.5 . . ?
H36c C36 H36a 109.5 . . ?
H36c C36 H36b 109.5 . . ?
H49a C49 C48 109.5 . . ?
H49b C49 C48 109.5 . . ?
H49b C49 H49a 109.5 . . ?
H49c C49 C48 109.5 . . ?
H49c C49 H49a 109.5 . . ?
H49c C49 H49b 109.5 . . ?
H50a C50 C48 109.5 . . ?
H50b C50 C48 109.5 . . ?
H50b C50 H50a 109.5 . . ?
H50c C50 C48 109.5 . . ?
H50c C50 H50a 109.5 . . ?
H50c C50 H50b 109.5 . . ?
H24a C24 C23 109.5 . . ?
H24b C24 C23 109.5 . . ?
H24b C24 H24a 109.5 . . ?
H24c C24 C23 109.5 . . ?
H24c C24 H24a 109.5 . . ?
H24c C24 H24b 109.5 . . ?
H33a C33 C32 109.5 . . ?
H33b C33 C32 109.5 . . ?
H33b C33 H33a 109.5 . . ?
H33c C33 C32 109.5 . . ?
H33c C33 H33a 109.5 . . ?
H33c C33 H33b 109.5 . . ?
H47a C47 C45 109.5 . . ?
H47b C47 C45 109.5 . . ?
H47b C47 H47a 109.5 . . ?
H47c C47 C45 109.5 . . ?
H47c C47 H47a 109.5 . . ?
H47c C47 H47b 109.5 . . ?
Cl2 C51 Cl1 113.6(3) . . ?
H51a C51 Cl1 108.9(3) . . ?
H51a C51 Cl2 108.9(3) . . ?
H51b C51 Cl1 108.9(4) . . ?
H51b C51 Cl2 108.9(3) . . ?
H51b C51 H51a 107.7 . . ?
H25a C25 C23 109.5 . . ?
H25b C25 C23 109.5 . . ?
H25b C25 H25a 109.5 . . ?
H25c C25 C23 109.5 . . ?
H25c C25 H25a 109.5 . . ?
H25c C25 H25b 109.5 . . ?
H46a C46 C45 109.5 . . ?
H46b C46 C45 109.5 . . ?
H46b C46 H46a 109.5 . . ?
H46c C46 C45 109.5 . . ?
H46c C46 H46a 109.5 . . ?
H46c C46 H46b 109.5 . . ?
H34a C34 C32 109.5 . . ?
H34b C34 C32 109.5 . . ?
H34b C34 H34a 109.5 . . ?
H34c C34 C32 109.5 . . ?
H34c C34 H34a 109.5 . . ?
H34c C34 H34b 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
O2 H2 O1 0.8200 1.727(3) 2.536(3) 168.5(3) .

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
O2 N2 C13 N1 3.4(2) . . . . ?
O2 N2 C14 C19 99.1(2) . . . . ?
O2 N2 C14 C15 -78.6(2) . . . . ?
O1 N3 C38 N4 0.9(3) . . . . ?
O1 N3 C39 C40 -105.8(2) . . . . ?
O1 N3 C39 C44 73.1(3) . . . . ?
N1 C13 N2 C14 174.7(2) . . . . ?
N1 C1 C2 C10 1.1(3) . . . . ?
N1 C1 C2 C3 -179.8(2) . . . . ?
N1 C1 C6 C7 -0.4(3) . . . . ?
N1 C1 C6 C5 179.8(3) . . . . ?
N2 C14 C19 C20 1.0(3) . . . . ?
N2 C14 C19 C18 -178.6(2) . . . . ?
N2 C14 C15 C23 -1.7(3) . . . . ?
N2 C14 C15 C16 177.7(3) . . . . ?
N4 C38 N3 C39 178.4(3) . . . . ?
N4 C26 C27 C35 0.1(3) . . . . ?
N4 C26 C27 C28 -179.2(2) . . . . ?
N4 C26 C31 C32 2.7(3) . . . . ?
N4 C26 C31 C30 179.6(3) . . . . ?
N3 C39 C40 C48 3.5(3) . . . . ?
N3 C39 C40 C41 -177.7(3) . . . . ?
N3 C39 C44 C45 -3.1(3) . . . . ?
N3 C39 C44 C43 178.8(3) . . . . ?
C1 C2 C10 C12 -131.1(4) . . . . ?
C1 C2 C10 C11 106.0(3) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C1 C6 C7 C9 -132.5(3) . . . . ?
C1 C6 C7 C8 101.3(4) . . . . ?
C1 C6 C5 C4 0.8(3) . . . . ?
C14 C19 C20 C21 109.9(3) . . . . ?
C14 C19 C20 C22 -125.5(3) . . . . ?
C14 C19 C18 C17 0.8(3) . . . . ?
C14 C15 C23 C24 -126.2(4) . . . . ?
C14 C15 C23 C25 108.3(4) . . . . ?
C14 C15 C16 C17 1.0(4) . . . . ?
C26 C27 C35 C37 -103.3(3) . . . . ?
C26 C27 C35 C36 132.0(4) . . . . ?
C26 C27 C28 C29 0.3(3) . . . . ?
C26 C31 C32 C33 115.3(4) . . . . ?
C26 C31 C32 C34 -120.5(6) . . . . ?
C26 C31 C30 C29 -1.2(4) . . . . ?
C39 C40 C48 C49 -109.6(4) . . . . ?
C39 C40 C48 C50 125.7(4) . . . . ?
C39 C40 C41 C42 -1.2(4) . . . . ?
C39 C44 C45 C47 -115.0(5) . . . . ?
C39 C44 C45 C46 117.6(5) . . . . ?
C39 C44 C43 C42 -0.9(4) . . . . ?
C19 C18 C17 C16 0.2(4) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C27 C28 C29 C30 0.9(4) . . . . ?
C6 C5 C4 C3 0.8(4) . . . . ?
C15 C16 C17 C18 -1.2(4) . . . . ?
C40 C41 C42 C43 -1.9(5) . . . . ?
C44 C43 C42 C41 3.0(5) . . . . ?
C31 C30 C29 C28 -0.4(4) . . . . ?


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

data_5
_database_code_depnum_ccdc_archive 'CCDC 2452449'
loop_
_audit_author_name
_audit_author_address
'Sizwe Zamisa'
;University of KwaZulu Natal
South Africa
;
_audit_update_record             
;
2025-05-19 deposited with the CCDC.	2025-09-12 downloaded from the CCDC.
;
_audit_creation_date             2025-04-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 F4 N2 O'
_chemical_formula_sum            'C13 H8 F4 N2 O'
_chemical_formula_weight         284.21
_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.5760(3)
_cell_length_b                   23.9624(8)
_cell_length_c                   13.8352(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.932(2)
_cell_angle_gamma                90
_cell_volume                     2466.05(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9158
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.67
_cell_measurement_theta_min      2.86
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1120 before and 0.0431 after correction.
The Ratio of minimum to maximum transmission is 0.9403.
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    1.531
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0099
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            95598
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         1.700
_diffrn_ambient_temperature      296.15
_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 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_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'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4196
_reflns_number_total             5045
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5045
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.053
_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)+(0.0504P)²+0.6577P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1146
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12), C16(H16),
 C17(H17), C18(H18), C20(H20), C23(H23), C24(H24), C25(H25)
1.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.36575(19) 0.81475(5) 0.33606(9) 0.0879(4) Uani 1 1 d . . . . .
F2 F 0.61021(16) 0.66274(5) 0.52996(8) 0.0760(3) Uani 1 1 d . . . . .
F3 F 0.37207(19) 0.55449(5) 0.46533(8) 0.0869(4) Uani 1 1 d . . . . .
F4 F 0.2130(2) 0.55822(5) 0.12091(8) 0.0873(4) Uani 1 1 d . . . . .
O1 O 0.49667(16) 0.71725(5) 0.26242(8) 0.0567(3) Uani 1 1 d . . . . .
H1 H 0.599149 0.705462 0.265283 0.085 Uiso 1 1 calc R U . . .
N1 N 0.43496(18) 0.70178(5) 0.34733(9) 0.0517(3) Uani 1 1 d . . . . .
N2 N 0.36625(17) 0.61384(5) 0.28376(9) 0.0495(3) Uani 1 1 d . . . . .
C1 C 0.4869(2) 0.73739(7) 0.42934(11) 0.0505(3) Uani 1 1 d . . . . .
C2 C 0.4555(3) 0.79429(7) 0.42222(13) 0.0636(4) Uani 1 1 d . . . . .
C3 C 0.5099(3) 0.82997(8) 0.49978(17) 0.0812(6) Uani 1 1 d . . . . .
H3 H 0.487858 0.868074 0.492745 0.097 Uiso 1 1 calc R U . . .
C4 C 0.5977(3) 0.80842(10) 0.58812(16) 0.0853(6) Uani 1 1 d . . . . .
H4 H 0.635611 0.832305 0.640950 0.102 Uiso 1 1 calc R U . . .
C5 C 0.6301(3) 0.75239(9) 0.59942(14) 0.0741(5) Uani 1 1 d . . . . .
H5 H 0.687611 0.738001 0.659621 0.089 Uiso 1 1 calc R U . . .
C6 C 0.5761(2) 0.71786(7) 0.52033(12) 0.0576(4) Uani 1 1 d . . . . .
C7 C 0.3691(2) 0.65013(6) 0.35268(11) 0.0489(3) Uani 1 1 d . . . . .
H7 H 0.323849 0.640175 0.408226 0.059 Uiso 1 1 calc R U . . .
C8 C 0.2949(2) 0.56007(7) 0.29277(11) 0.0511(4) Uani 1 1 d . . . . .
C9 C 0.3005(3) 0.52942(8) 0.37889(13) 0.0637(4) Uani 1 1 d . . . . .
C10 C 0.2430(3) 0.47541(9) 0.38092(17) 0.0823(6) Uani 1 1 d . . . . .
H10 H 0.249107 0.457005 0.440652 0.099 Uiso 1 1 calc R U . . .
C11 C 0.1758(3) 0.44851(9) 0.29371(18) 0.0840(6) Uani 1 1 d . . . . .
H11 H 0.137550 0.411649 0.294215 0.101 Uiso 1 1 calc R U . . .
C12 C 0.1655(3) 0.47635(8) 0.20581(16) 0.0751(5) Uani 1 1 d . . . . .
H12 H 0.119865 0.458731 0.146441 0.090 Uiso 1 1 calc R U . . .
C13 C 0.2239(2) 0.53057(7) 0.20747(12) 0.0613(4) Uani 1 1 d . . . . .
F5 F 0.89170(19) 0.77469(4) 0.30574(9) 0.0901(4) Uani 1 1 d . . . . .
F6 F 0.97390(18) 0.60891(4) 0.48928(8) 0.0816(3) Uani 1 1 d . . . . .
F7 F 0.71097(18) 0.52259(5) 0.36995(8) 0.0803(3) Uani 1 1 d . . . . .
F8 F 0.7286(2) 0.53461(5) 0.03413(8) 0.0932(4) Uani 1 1 d . . . . .
O2 O 0.59877(16) 0.61956(5) 0.15248(8) 0.0574(3) Uani 1 1 d . . . . .
H2 H 0.517863 0.623934 0.183619 0.086 Uiso 1 1 calc R U . . .
N3 N 0.81857(18) 0.66532(5) 0.30948(10) 0.0516(3) Uani 1 1 d . . . . .
N4 N 0.73846(19) 0.58910(5) 0.20924(10) 0.0543(3) Uani 1 1 d . . . . .
C14 C 0.9291(2) 0.69027(6) 0.39189(12) 0.0510(4) Uani 1 1 d . . . . .
C15 C 0.9582(2) 0.74761(7) 0.39093(14) 0.0616(4) Uani 1 1 d . . . . .
C16 C 1.0480(3) 0.77739(8) 0.46996(16) 0.0715(5) Uani 1 1 d . . . . .
H16 H 1.063290 0.815742 0.465321 0.086 Uiso 1 1 calc R U . . .
C17 C 1.1150(3) 0.74966(9) 0.55593(15) 0.0704(5) Uani 1 1 d . . . . .
H17 H 1.176596 0.769243 0.609997 0.084 Uiso 1 1 calc R U . . .
C18 C 1.0913(3) 0.69295(9) 0.56222(14) 0.0683(5) Uani 1 1 d . . . . .
H18 H 1.136269 0.673983 0.620318 0.082 Uiso 1 1 calc R U . . .
C19 C 0.9999(2) 0.66459(7) 0.48127(13) 0.0577(4) Uani 1 1 d . . . . .
C20 C 0.8427(2) 0.61450(6) 0.28623(12) 0.0519(4) Uani 1 1 d . . . . .
H20 H 0.935854 0.594383 0.324081 0.062 Uiso 1 1 calc R U . . .
C21 C 0.7194(2) 0.53045(6) 0.20216(12) 0.0537(4) Uani 1 1 d . . . . .
C22 C 0.7022(3) 0.49732(7) 0.28181(13) 0.0635(4) Uani 1 1 d . . . . .
C23 C 0.6770(3) 0.44084(8) 0.27459(18) 0.0844(6) Uani 1 1 d . . . . .
H23 H 0.667784 0.419636 0.329721 0.101 Uiso 1 1 calc R U . . .
C24 C 0.6657(4) 0.41621(9) 0.1842(2) 0.0979(8) Uani 1 1 d . . . . .
H24 H 0.647679 0.377879 0.178123 0.117 Uiso 1 1 calc R U . . .
C25 C 0.6803(3) 0.44698(9) 0.10252(18) 0.0906(7) Uani 1 1 d . . . . .
H25 H 0.670611 0.429854 0.041420 0.109 Uiso 1 1 calc R U . . .
C26 C 0.7095(3) 0.50341(8) 0.11220(14) 0.0683(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.348(2) . ?
F2 C6 1.348(2) . ?
F3 C9 1.356(2) . ?
F4 C13 1.357(2) . ?
O1 H1 0.8200 . ?
O1 N1 1.3943(16) . ?
N1 C1 1.4146(19) . ?
N1 C7 1.342(2) . ?
N2 C7 1.2877(19) . ?
N2 C8 1.412(2) . ?
C1 C2 1.385(2) . ?
C1 C6 1.392(2) . ?
C2 C3 1.373(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.368(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.371(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(2) . ?
C8 C13 1.393(2) . ?
C9 C10 1.368(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.371(3) . ?
F5 C15 1.356(2) . ?
F6 C19 1.3563(19) . ?
F7 C22 1.352(2) . ?
F8 C26 1.344(2) . ?
O2 H2 0.8200 . ?
O2 N4 1.3979(17) . ?
N3 C14 1.413(2) . ?
N3 C20 1.2814(19) . ?
N4 C20 1.345(2) . ?
N4 C21 1.414(2) . ?
C14 C15 1.392(2) . ?
C14 C19 1.394(2) . ?
C15 C16 1.373(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.373(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.376(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.379(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.384(2) . ?
C21 C26 1.392(2) . ?
C22 C23 1.368(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.371(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.371(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.373(3) . ?

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
N1 O1 H1 109.5 . . ?
O1 N1 C1 115.39(12) . . ?
C7 N1 O1 118.64(12) . . ?
C7 N1 C1 124.18(13) . . ?
C7 N2 C8 120.26(13) . . ?
C2 C1 N1 121.27(14) . . ?
C2 C1 C6 116.29(15) . . ?
C6 C1 N1 122.42(14) . . ?
F1 C2 C1 118.18(15) . . ?
F1 C2 C3 119.43(17) . . ?
C3 C2 C1 122.38(18) . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 118.91(19) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.04(18) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.75(19) . . ?
C6 C5 H5 120.6 . . ?
F2 C6 C1 118.04(14) . . ?
F2 C6 C5 119.33(16) . . ?
C5 C6 C1 122.63(17) . . ?
N1 C7 H7 118.8 . . ?
N2 C7 N1 122.43(14) . . ?
N2 C7 H7 118.8 . . ?
C9 C8 N2 127.33(14) . . ?
C13 C8 N2 118.75(14) . . ?
C13 C8 C9 113.65(15) . . ?
F3 C9 C8 117.57(15) . . ?
F3 C9 C10 118.47(17) . . ?
C10 C9 C8 123.94(17) . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.41(19) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.79(19) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.72(18) . . ?
C13 C12 H12 120.6 . . ?
F4 C13 C8 116.67(15) . . ?
F4 C13 C12 118.83(16) . . ?
C12 C13 C8 124.49(17) . . ?
N4 O2 H2 109.5 . . ?
C20 N3 C14 120.92(14) . . ?
O2 N4 C21 115.05(13) . . ?
C20 N4 O2 118.47(12) . . ?
C20 N4 C21 122.78(14) . . ?
C15 C14 N3 118.72(15) . . ?
C15 C14 C19 114.16(15) . . ?
C19 C14 N3 126.76(14) . . ?
F5 C15 C14 116.57(15) . . ?
F5 C15 C16 119.33(16) . . ?
C16 C15 C14 124.10(18) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 118.97(18) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.10(18) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.4 . . ?
C17 C18 C19 119.15(18) . . ?
C19 C18 H18 120.4 . . ?
F6 C19 C14 117.99(15) . . ?
F6 C19 C18 118.47(16) . . ?
C18 C19 C14 123.52(16) . . ?
N3 C20 N4 122.59(15) . . ?
N3 C20 H20 118.7 . . ?
N4 C20 H20 118.7 . . ?
C22 C21 N4 122.58(14) . . ?
C22 C21 C26 116.58(16) . . ?
C26 C21 N4 120.79(16) . . ?
F7 C22 C21 117.74(15) . . ?
F7 C22 C23 119.43(18) . . ?
C23 C22 C21 122.83(18) . . ?
C22 C23 H23 120.8 . . ?
C22 C23 C24 118.4(2) . . ?
C24 C23 H23 120.8 . . ?
C23 C24 H24 119.4 . . ?
C23 C24 C25 121.3(2) . . ?
C25 C24 H24 119.4 . . ?
C24 C25 H25 120.5 . . ?
C24 C25 C26 119.1(2) . . ?
C26 C25 H25 120.5 . . ?
F8 C26 C21 117.63(16) . . ?
F8 C26 C25 120.63(18) . . ?
C25 C26 C21 121.74(19) . . ?

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
O1 H1 N3 0.82 1.92 2.7051(17) 160.7 . yes
O2 H2 N2 0.82 1.98 2.7630(17) 160.9 . 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 C2 C3 C4 178.5(2) . . . . ?
F3 C9 C10 C11 -177.7(2) . . . . ?
O1 N1 C1 C2 53.1(2) . . . . ?
O1 N1 C1 C6 -125.11(16) . . . . ?
O1 N1 C7 N2 2.3(2) . . . . ?
N1 C1 C2 F1 3.2(3) . . . . ?
N1 C1 C2 C3 -177.76(18) . . . . ?
N1 C1 C6 F2 -1.3(2) . . . . ?
N1 C1 C6 C5 178.56(16) . . . . ?
N2 C8 C9 F3 4.4(3) . . . . ?
N2 C8 C9 C10 -173.70(19) . . . . ?
N2 C8 C13 F4 -6.1(2) . . . . ?
N2 C8 C13 C12 173.87(18) . . . . ?
C1 N1 C7 N2 -161.75(14) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C1 C6 F2 -179.56(15) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C4 C5 C6 F2 178.73(18) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
C6 C1 C2 F1 -178.47(16) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C7 N1 C1 C2 -142.38(17) . . . . ?
C7 N1 C1 C6 39.4(2) . . . . ?
C7 N2 C8 C9 -33.0(2) . . . . ?
C7 N2 C8 C13 153.39(15) . . . . ?
C8 N2 C7 N1 -179.78(14) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C9 C8 C13 F4 179.39(16) . . . . ?
C9 C8 C13 C12 -0.6(3) . . . . ?
C9 C10 C11 C12 -0.7(4) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C11 C12 C13 F4 -179.65(19) . . . . ?
C11 C12 C13 C8 0.4(3) . . . . ?
C13 C8 C9 F3 178.34(16) . . . . ?
C13 C8 C9 C10 0.2(3) . . . . ?
F5 C15 C16 C17 -179.96(17) . . . . ?
F7 C22 C23 C24 179.0(2) . . . . ?
O2 N4 C20 N3 0.1(2) . . . . ?
O2 N4 C21 C22 -116.71(17) . . . . ?
O2 N4 C21 C26 60.6(2) . . . . ?
N3 C14 C15 F5 -6.4(2) . . . . ?
N3 C14 C15 C16 173.42(17) . . . . ?
N3 C14 C19 F6 5.6(2) . . . . ?
N3 C14 C19 C18 -172.96(16) . . . . ?
N4 C21 C22 F7 -2.5(3) . . . . ?
N4 C21 C22 C23 177.49(18) . . . . ?
N4 C21 C26 F8 3.6(3) . . . . ?
N4 C21 C26 C25 -176.06(19) . . . . ?
C14 N3 C20 N4 178.96(14) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C15 C14 C19 F6 178.50(15) . . . . ?
C15 C14 C19 C18 -0.1(2) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C16 C17 C18 C19 0.1(3) . . . . ?
C17 C18 C19 F6 -178.50(16) . . . . ?
C17 C18 C19 C14 0.1(3) . . . . ?
C19 C14 C15 F5 -179.89(15) . . . . ?
C19 C14 C15 C16 -0.1(3) . . . . ?
C20 N3 C14 C15 151.06(16) . . . . ?
C20 N3 C14 C19 -36.4(2) . . . . ?
C20 N4 C21 C22 41.2(2) . . . . ?
C20 N4 C21 C26 -141.50(17) . . . . ?
C21 N4 C20 N3 -157.12(15) . . . . ?
C21 C22 C23 C24 -1.0(3) . . . . ?
C22 C21 C26 F8 -179.00(17) . . . . ?
C22 C21 C26 C25 1.4(3) . . . . ?
C22 C23 C24 C25 0.5(4) . . . . ?
C23 C24 C25 C26 1.0(4) . . . . ?
C24 C25 C26 F8 178.5(2) . . . . ?
C24 C25 C26 C21 -1.9(4) . . . . ?
C26 C21 C22 F7 -179.88(16) . . . . ?
C26 C21 C22 C23 0.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

