# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_TIT1533F11-15_130K
_database_code_depnum_ccdc_archive 'CCDC 1878132'
_audit_update_record             
;
2018-11-09 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;
_audit_creation_date             2018-11-09
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_chemical_compound_source        'Titouan Royal'

_exptl_crystal_recrystallization_method 
; 
cyclohexane
;


_chemical_formula_moiety         'C24 H22 F N O4'
_chemical_formula_sum            'C24 H22 F N O4'
_chemical_formula_weight         407.44
_chemical_absolute_configuration unk
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
H -0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
C 0.01480 0.00700 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
F 0.06000 0.04110 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
O 0.04120 0.02500 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
N 0.02530 0.01360 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom

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

_symmetry_Int_Tables_number      4
_cell_length_a                   15.3747(2)
_cell_length_b                   7.24010(10)
_cell_length_c                   18.6840(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.0660(10)
_cell_angle_gamma                90
_cell_volume                     2033.85(5)
_cell_formula_units_Z            4

_cell_measurement_temperature    130
_cell_measurement_reflns_used    89515
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      57.46
_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.040

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270.
Afterwards scaling of reflection intensities was performed within STOE LANA.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Finally a spherical absorption correction was done within STOE LANA.
;
_exptl_absorpt_correction_T_min  0.3571
_exptl_absorpt_correction_T_max  0.9497

_exptl_absorpt_coefficient_mu    0.512
_exptl_crystal_density_diffrn    1.3305
_exptl_crystal_F_000             856
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            41456
_diffrn_reflns_theta_full        57.0832
_diffrn_reflns_theta_max         57.08
_diffrn_reflns_theta_min         2.56
_diffrn_measured_fraction_theta_full 0.9705
_diffrn_measured_fraction_theta_max 0.9705

_diffrn_ambient_temperature      130
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 6288 frames, detector distance = 60 mm
;

_diffrn_measurement_device_type  'Stoe StadiVari'
_diffrn_measurement_device       Area
_diffrn_detector                 Pilatus300K
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Metaljet D2'
_diffrn_source_voltage           70
_diffrn_source_current           2.860
_diffrn_source_power             0.200
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34143
_reflns_Friedel_coverage         0.947
_reflns_limit_h_max              19
_reflns_limit_h_min              -18
_reflns_limit_k_max              9
_reflns_limit_k_min              -8
_reflns_limit_l_max              23
_reflns_limit_l_min              -22
_reflns_number_gt                7479
_reflns_number_total             8088
_reflns_threshold_expression     I>=2u(I)



_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)
;
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
X-Area Integrate 1.73.1.0 (STOE, 2018)
X-Area LANA 1.73.2.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.1677
_refine_diff_density_min         -0.3316
_refine_diff_density_rms         0.0451
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.07(13)
_refine_ls_d_res_high            0.7990
_refine_ls_d_res_low             15.0350
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0474
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    78
_refine_ls_number_parameters     544
_refine_ls_number_reflns         8088
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.0474
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0802P)²+0.3205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1133
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C43(H43), C45(H45)
2.b Secondary CH2 refined with riding coordinates:
 C31(H31a,H31b), C46(H46a,H46b), C54(H54a,H54b), C50(H50a,H50b), C55(H55a,
 H55b), C59(H59a,H59b)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C24(H24), C26(H26), C27(H27), C35(H35), C38(H38),
 C39(H39), C51(H51), C52(H52), C57(H57), C58(H58), C14(H14), C15(H15), C28(H28),
  C29(H29), C33(H33), C34(H34), C36(H36), C37(H37), C40(H40), C48(H48),
 C53(H53), C56(H56)
2.d Idealised Me refined as rotating group:
 C49(H49a,H49b,H49c), C60(H60a,H60b,H60c)
;
_atom_sites_solution_primary     iterative
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
F5 F 0.00112(9) -0.38688(18) -0.15833(7) 0.0493(3) Uani 1.000000 .
O2 O -0.16857(8) -0.7074(2) -0.27817(7) 0.0310(3) Uani 1.000000 .
O8 O 0.17907(9) -0.7239(2) -0.75683(7) 0.0389(3) Uani 1.000000 .
O9 O -0.27556(8) -0.5765(2) -0.36291(7) 0.0393(3) Uani 1.000000 .
O10 O 0.28385(9) -0.6014(2) -0.67556(8) 0.0426(4) Uani 1.000000 .
N13 N 0.20853(10) -0.6613(2) -0.69533(8) 0.0285(3) Uani 1.000000 .
C12 C -0.02119(11) -0.6537(2) -0.49133(9) 0.0227(3) Uani 1.000000 .
C19 C 0.12795(11) -0.6023(2) -0.52226(9) 0.0240(3) Uani 1.000000 .
H19 H 0.15007(11) -0.5658(2) -0.47417(9) 0.0288(4) Uiso 1.000000 R
C20 C 0.00849(11) -0.7036(2) -0.41763(9) 0.0235(3) Uani 1.000000 .
H20 H 0.06755(11) -0.7379(2) -0.40088(9) 0.0282(4) Uiso 1.000000 R
C23 C -0.20158(12) -0.6391(2) -0.34450(10) 0.0258(4) Uani 1.000000 .
C24 C -0.04876(11) -0.7027(2) -0.36967(9) 0.0239(3) Uani 1.000000 .
H24 H -0.02847(11) -0.7389(2) -0.32130(9) 0.0287(4) Uiso 1.000000 R
C25 C 0.14933(12) -0.6586(2) -0.64287(9) 0.0245(3) Uani 1.000000 .
C26 C 0.00693(12) -0.7129(2) -0.61623(9) 0.0255(3) Uani 1.000000 .
H26 H -0.05214(12) -0.7490(2) -0.63113(9) 0.0306(4) Uiso 1.000000 R
C27 C -0.16651(11) -0.5928(2) -0.46610(9) 0.0238(3) Uani 1.000000 .
H27 H -0.22470(11) -0.5519(2) -0.48194(9) 0.0286(4) Uiso 1.000000 R
C30 C -0.13684(11) -0.6475(2) -0.39366(9) 0.0227(3) Uani 1.000000 .
C31 C -0.22712(12) -0.6959(3) -0.22631(10) 0.0337(4) Uani 1.000000 .
H31a H -0.24103(12) -0.5679(3) -0.21834(10) 0.0405(5) Uiso 1.000000 R
H31b H -0.28228(12) -0.7609(3) -0.24532(10) 0.0405(5) Uiso 1.000000 R
C32 C 0.03872(11) -0.6572(2) -0.54386(9) 0.0227(3) Uani 1.000000 .
C35 C 0.06220(11) -0.7152(2) -0.66611(9) 0.0257(3) Uani 1.000000 .
H35 H 0.04113(11) -0.7540(2) -0.71406(9) 0.0308(4) Uiso 1.000000 R
C38 C 0.18310(11) -0.6020(2) -0.57182(9) 0.0242(3) Uani 1.000000 .
H38 H 0.24204(11) -0.5645(2) -0.55765(9) 0.0290(4) Uiso 1.000000 R
C39 C -0.10974(11) -0.5989(2) -0.51467(9) 0.0241(3) Uani 1.000000 .
H39 H -0.13079(11) -0.5662(2) -0.56335(9) 0.0290(4) Uiso 1.000000 R
C41 C -0.01737(12) -0.7085(3) -0.15106(10) 0.0298(4) Uani 1.000000 .
C43 C -0.09613(11) -0.6835(3) -0.11469(9) 0.0279(4) Uani 1.000000 .
H43 H -0.10962(11) -0.5512(3) -0.11524(9) 0.0335(4) Uiso 1.000000 R
C46 C -0.07063(13) -0.7440(3) -0.03408(10) 0.0351(4) Uani 1.000000 .
H46a H -0.06696(13) -0.8778(3) -0.03208(10) 0.0421(5) Uiso 1.000000 R
H46b H -0.01213(13) -0.6955(3) -0.01279(10) 0.0421(5) Uiso 1.000000 R
C47 C 0.02874(13) -0.5584(3) -0.17002(10) 0.0371(5) Uani 1.000000 .
C49 C -0.13611(15) -0.6797(4) 0.01183(11) 0.0444(5) Uani 1.000000 .
H49a H -0.1936(3) -0.732(2) -0.0074(6) 0.0666(8) Uiso 1.000000 GR
H49b H -0.1157(7) -0.719(2) 0.0616(2) 0.0666(8) Uiso 1.000000 GR
H49c H -0.1402(9) -0.5474(4) 0.0102(8) 0.0666(8) Uiso 1.000000 GR
C51 C 0.08847(15) -0.9019(4) -0.19557(12) 0.0503(6) Uani 1.000000 .
H51 H 0.10894(15) -1.0192(4) -0.20392(12) 0.0604(7) Uiso 1.000000 R
C52 C 0.01480(14) -0.8820(3) -0.16445(11) 0.0391(5) Uani 1.000000 .
H52 H -0.01382(14) -0.9869(3) -0.15222(11) 0.0470(6) Uiso 1.000000 R
C54 C -0.17986(12) -0.7825(3) -0.15538(10) 0.0309(4) Uani 1.000000 .
H54a H -0.22147(12) -0.7901(3) -0.12297(10) 0.0371(5) Uiso 1.000000 R
H54b H -0.16372(12) -0.9079(3) -0.16556(10) 0.0371(5) Uiso 1.000000 R
C57 C 0.13181(14) -0.7463(5) -0.21434(11) 0.0558(8) Uani 1.000000 .
H57 H 0.18112(14) -0.7596(5) -0.23546(11) 0.0669(9) Uiso 1.000000 R
C58 C 0.10184(13) -0.5730(4) -0.20172(11) 0.0495(6) Uani 1.000000 .
H58 H 0.13017(13) -0.4680(4) -0.21425(11) 0.0594(8) Uiso 1.000000 R
F21 F -0.64578(12) -0.6160(2) -0.82673(8) 0.0650(4) Uani 1.000000 .
O1 O -0.40637(9) -0.45625(19) -0.74849(7) 0.0315(3) Uani 1.000000 .
O3 O -0.63792(11) -0.4293(2) -0.21318(8) 0.0454(4) Uani 1.000000 .
O7 O -0.28365(9) -0.3192(2) -0.68487(7) 0.0409(4) Uani 1.000000 .
O11 O -0.75422(10) -0.3270(2) -0.28773(9) 0.0467(4) Uani 1.000000 .
N6 N -0.67692(11) -0.3796(2) -0.27425(9) 0.0333(4) Uani 1.000000 .
C4 C -0.62779(12) -0.3781(2) -0.33373(10) 0.0257(4) Uani 1.000000 .
C14 C -0.62670(11) -0.3227(2) -0.45881(9) 0.0240(3) Uani 1.000000 .
H14 H -0.65584(11) -0.2865(2) -0.50542(9) 0.0288(4) Uiso 1.000000 R
C15 C -0.35883(11) -0.3283(2) -0.55767(9) 0.0231(3) Uani 1.000000 .
H15 H -0.29951(11) -0.2930(2) -0.55094(9) 0.0277(4) Uiso 1.000000 R
C16 C -0.40493(11) -0.3794(2) -0.62698(9) 0.0229(3) Uani 1.000000 .
C17 C -0.35709(12) -0.3806(2) -0.68855(10) 0.0261(4) Uani 1.000000 .
C18 C -0.49045(11) -0.3744(2) -0.50883(9) 0.0215(3) Uani 1.000000 .
C22 C -0.53667(11) -0.3743(2) -0.44654(9) 0.0215(3) Uani 1.000000 .
C28 C -0.53836(12) -0.4273(3) -0.31905(10) 0.0278(4) Uani 1.000000 .
H28 H -0.50950(12) -0.4606(3) -0.27200(10) 0.0333(4) Uiso 1.000000 R
C29 C -0.53681(11) -0.4214(2) -0.57867(9) 0.0239(3) Uani 1.000000 .
H29 H -0.59701(11) -0.4499(2) -0.58599(9) 0.0287(4) Uiso 1.000000 R
C33 C -0.49480(11) -0.4266(2) -0.63761(9) 0.0245(3) Uani 1.000000 .
H33 H -0.52622(11) -0.4612(2) -0.68375(9) 0.0294(4) Uiso 1.000000 R
C34 C -0.40005(11) -0.3292(2) -0.49864(9) 0.0226(3) Uani 1.000000 .
H34 H -0.36781(11) -0.2998(2) -0.45217(9) 0.0271(4) Uiso 1.000000 R
C36 C -0.67231(11) -0.3251(2) -0.40289(10) 0.0257(3) Uani 1.000000 .
H36 H -0.73200(11) -0.2918(2) -0.41138(10) 0.0308(4) Uiso 1.000000 R
C37 C -0.49330(11) -0.4258(2) -0.37562(10) 0.0248(3) Uani 1.000000 .
H37 H -0.43360(11) -0.4592(2) -0.36668(10) 0.0298(4) Uiso 1.000000 R
C40 C -0.63547(13) -0.4638(3) -1.00616(11) 0.0338(4) Uani 1.000000 .
H40 H -0.60046(13) -0.3900(3) -1.02956(11) 0.0406(5) Uiso 1.000000 R
C42 C -0.66805(13) -0.5922(3) -0.89949(10) 0.0350(4) Uani 1.000000 .
C44 C -0.61326(12) -0.4797(3) -0.93071(10) 0.0302(4) Uani 1.000000 .
C45 C -0.53305(12) -0.3850(3) -0.88329(10) 0.0316(4) Uani 1.000000 .
H45 H -0.54569(12) -0.3708(3) -0.83430(10) 0.0380(5) Uiso 1.000000 R
C48 C -0.74179(14) -0.6828(3) -0.93978(13) 0.0415(5) Uani 1.000000 .
H48 H -0.77720(14) -0.7560(3) -0.91654(13) 0.0498(6) Uiso 1.000000 R
C50 C -0.37309(12) -0.4499(3) -0.81595(10) 0.0308(4) Uani 1.000000 .
H50a H -0.35420(12) -0.3259(3) -0.82507(10) 0.0369(5) Uiso 1.000000 R
H50b H -0.32312(12) -0.5333(3) -0.81326(10) 0.0369(5) Uiso 1.000000 R
C53 C -0.76175(14) -0.6624(3) -1.01489(12) 0.0403(5) Uani 1.000000 .
H53 H -0.81105(14) -0.7216(3) -1.04282(12) 0.0483(6) Uiso 1.000000 R
C55 C -0.45076(13) -0.5098(3) -0.87574(10) 0.0314(4) Uani 1.000000 .
H55a H -0.46734(13) -0.6349(3) -0.86565(10) 0.0376(5) Uiso 1.000000 R
H55b H -0.43168(13) -0.5113(3) -0.92205(10) 0.0376(5) Uiso 1.000000 R
C56 C -0.70829(14) -0.5542(3) -1.04814(11) 0.0403(5) Uani 1.000000 .
H56 H -0.72087(14) -0.5415(3) -1.09879(11) 0.0484(6) Uiso 1.000000 R
C59 C -0.51622(14) -0.1918(3) -0.91062(14) 0.0445(5) Uani 1.000000 .
H59a H -0.46299(14) -0.1419(3) -0.87940(14) 0.0534(6) Uiso 1.000000 R
H59b H -0.50501(14) -0.2022(3) -0.95966(14) 0.0534(6) Uiso 1.000000 R
C60 C -0.59224(18) -0.0569(4) -0.91210(17) 0.0587(7) Uani 1.000000 .
H60a H -0.6429(5) -0.0955(18) -0.9483(9) 0.0880(10) Uiso 1.000000 GR
H60b H -0.6076(10) -0.054(2) -0.8649(4) 0.0880(10) Uiso 1.000000 GR
H60c H -0.5742(6) 0.0642(7) -0.9241(13) 0.0880(10) 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
F5 C47 1.345(3) . ?
O2 C23 1.332(2) . ?
O2 C31 1.456(2) . ?
O8 N13 1.230(2) . ?
O9 C23 1.206(2) . ?
O10 N13 1.219(2) . ?
N13 C25 1.471(2) . ?
C12 C20 1.404(2) . ?
C12 C32 1.480(2) . ?
C12 C39 1.397(2) . ?
C19 C32 1.404(2) . ?
C19 C38 1.380(2) . ?
C20 C24 1.381(2) . ?
C23 C30 1.490(2) . ?
C24 C30 1.393(2) . ?
C25 C35 1.381(2) . ?
C25 C38 1.382(2) . ?
C26 C32 1.398(2) . ?
C26 C35 1.386(2) . ?
C27 C30 1.393(2) . ?
C27 C39 1.385(2) . ?
C31 C54 1.508(3) . ?
C41 C43 1.518(2) . ?
C41 C47 1.384(3) . ?
C41 C52 1.392(3) . ?
C43 C46 1.539(2) . ?
C43 C54 1.530(3) . ?
C46 C49 1.526(3) . ?
C47 C58 1.380(3) . ?
C51 C52 1.385(3) . ?
C51 C57 1.390(4) . ?
C57 C58 1.374(4) . ?
F21 C42 1.342(2) . ?
O1 C17 1.332(2) . ?
O1 C50 1.457(2) . ?
O3 N6 1.227(2) . ?
O7 C17 1.202(2) . ?
O11 N6 1.223(2) . ?
N6 C4 1.469(2) . ?
C4 C28 1.391(3) . ?
C4 C36 1.384(3) . ?
C14 C22 1.405(2) . ?
C14 C36 1.375(2) . ?
C15 C16 1.390(2) . ?
C15 C34 1.382(2) . ?
C16 C17 1.489(2) . ?
C16 C33 1.397(2) . ?
C18 C22 1.485(2) . ?
C18 C29 1.392(2) . ?
C18 C34 1.402(2) . ?
C22 C37 1.403(2) . ?
C28 C37 1.380(2) . ?
C29 C33 1.389(2) . ?
C40 C44 1.384(3) . ?
C40 C56 1.389(3) . ?
C42 C44 1.385(3) . ?
C42 C48 1.387(3) . ?
C44 C45 1.523(3) . ?
C45 C55 1.537(3) . ?
C45 C59 1.529(3) . ?
C48 C53 1.380(3) . ?
C50 C55 1.518(3) . ?
C53 C56 1.375(3) . ?
C59 C60 1.519(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
C31 O2 C23 115.43(13) . . ?
O10 N13 O8 123.71(15) . . ?
C25 N13 O8 117.98(14) . . ?
C25 N13 O10 118.31(15) . . ?
C32 C12 C20 121.74(15) . . ?
C39 C12 C20 118.34(15) . . ?
C39 C12 C32 119.91(15) . . ?
C38 C19 C32 120.53(15) . . ?
C24 C20 C12 120.95(15) . . ?
O9 C23 O2 123.92(16) . . ?
C30 C23 O2 112.60(14) . . ?
C30 C23 O9 123.47(16) . . ?
C30 C24 C20 120.09(15) . . ?
C35 C25 N13 118.76(15) . . ?
C38 C25 N13 118.91(15) . . ?
C38 C25 C35 122.32(16) . . ?
C35 C26 C32 120.95(15) . . ?
C39 C27 C30 120.30(15) . . ?
C24 C30 C23 122.91(15) . . ?
C27 C30 C23 117.53(14) . . ?
C27 C30 C24 119.54(15) . . ?
C54 C31 O2 108.04(14) . . ?
C19 C32 C12 120.71(15) . . ?
C26 C32 C12 120.41(15) . . ?
C26 C32 C19 118.87(16) . . ?
C26 C35 C25 118.39(15) . . ?
C25 C38 C19 118.93(15) . . ?
C27 C39 C12 120.73(15) . . ?
C47 C41 C43 121.35(18) . . ?
C52 C41 C43 122.33(18) . . ?
C52 C41 C47 116.27(18) . . ?
C46 C43 C41 109.89(14) . . ?
C54 C43 C41 112.88(15) . . ?
C54 C43 C46 111.63(15) . . ?
C49 C46 C43 113.60(16) . . ?
C41 C47 F5 119.18(18) . . ?
C58 C47 F5 117.0(2) . . ?
C58 C47 C41 123.8(2) . . ?
C57 C51 C52 119.9(2) . . ?
C51 C52 C41 121.5(2) . . ?
C43 C54 C31 116.26(16) . . ?
C58 C57 C51 120.07(19) . . ?
C57 C58 C47 118.4(2) . . ?
C50 O1 C17 118.28(14) . . ?
O11 N6 O3 123.22(16) . . ?
C4 N6 O3 118.51(16) . . ?
C4 N6 O11 118.25(15) . . ?
C28 C4 N6 119.50(16) . . ?
C36 C4 N6 118.45(15) . . ?
C36 C4 C28 122.04(15) . . ?
C36 C14 C22 120.94(15) . . ?
C34 C15 C16 120.83(15) . . ?
C17 C16 C15 118.89(15) . . ?
C33 C16 C15 119.62(15) . . ?
C33 C16 C17 121.49(15) . . ?
O7 C17 O1 124.24(16) . . ?
C16 C17 O1 111.47(14) . . ?
C16 C17 O7 124.29(16) . . ?
C29 C18 C22 119.97(15) . . ?
C34 C18 C22 121.12(15) . . ?
C34 C18 C29 118.90(15) . . ?
C18 C22 C14 119.25(15) . . ?
C37 C22 C14 118.80(15) . . ?
C37 C22 C18 121.95(15) . . ?
C37 C28 C4 118.74(16) . . ?
C33 C29 C18 121.20(15) . . ?
C29 C33 C16 119.40(16) . . ?
C18 C34 C15 119.99(15) . . ?
C14 C36 C4 118.81(16) . . ?
C28 C37 C22 120.66(16) . . ?
C56 C40 C44 122.27(19) . . ?
C44 C42 F21 116.96(17) . . ?
C48 C42 F21 119.69(18) . . ?
C48 C42 C44 123.32(18) . . ?
C42 C44 C40 115.82(17) . . ?
C45 C44 C40 123.54(18) . . ?
C45 C44 C42 120.62(17) . . ?
C55 C45 C44 109.86(15) . . ?
C59 C45 C44 112.98(16) . . ?
C59 C45 C55 111.99(16) . . ?
C53 C48 C42 118.94(19) . . ?
C55 C50 O1 105.27(14) . . ?
C56 C53 C48 119.57(19) . . ?
C50 C55 C45 113.93(15) . . ?
C53 C56 C40 120.07(19) . . ?
C60 C59 C45 114.3(2) . . ?

_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_TIT1533F25_130K
_database_code_depnum_ccdc_archive 'CCDC 1884922'
_audit_update_record             
;
2018-12-13 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;
_audit_creation_date             2018-12-13
_audit_creation_method           CRYSTALS_ver_14.61_build_7031

_oxford_structure_analysis_title 'TIT1533F25_130K_0m in P2(1)'
_chemical_name_systematic        .
_chemical_melting_point          'not measured'
_chemical_compound_source        'T. Royal'

_exptl_crystal_recrystallization_method 
; 
Cyclohexane
;

_refine_special_details          
; 
? 
;
#end of refcif 
_cell_length_a                   15.3844(8)
_cell_length_b                   7.2248(4)
_cell_length_c                   18.6689(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.1332(18)
_cell_angle_gamma                90
_cell_volume                     2028.68(19)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z

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_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C24 H22 F1 N1 O4 
# Dc =      1.33 Fooo =    856.00 Mu =      8.00 M =    407.44
# Found Formula = C24 H22 F1 N1 O4 
# Dc =      1.33 FOOO =    856.00 Mu =      8.00 M =    407.44

_chemical_formula_sum            'C24 H22 F1 N1 O4'
_chemical_formula_moiety         'C24 H22 F1 N1 O4'
_chemical_formula_weight         407.44


_cell_measurement_reflns_used    9990
_cell_measurement_theta_min      3
_cell_measurement_theta_max      70
_cell_measurement_temperature    130

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.070
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_max          0.300

_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.800

# Sheldrick geometric approximatio 0.82 0.57 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_T_max  0.57
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      130
_diffrn_reflns_number            27443
_diffrn_reflns_av_unetI/netI     0.037
_reflns_number_total             7436
_diffrn_reflns_av_R_equivalents  0.027
# Number of reflections without Friedels Law is 7436 
# Number of reflections with Friedels Law is 4091 
# Theoretical number of reflections is about 3858 


_diffrn_reflns_theta_min         4.183
_diffrn_reflns_theta_max         70.141
_diffrn_measured_fraction_theta_max 0.979

_diffrn_reflns_theta_full        68.000
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_reflns_limit_h_min              -18
_reflns_limit_h_max              18
_reflns_limit_k_min              -8
_reflns_limit_k_max              8
_reflns_limit_l_min              0
_reflns_limit_l_max              22

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.32
_refine_diff_density_max         1.05


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_restraints     1
_refine_ls_number_parameters     542
_refine_ls_number_reflns         7435
_oxford_refine_ls_R_factor_ref   0.0356
_refine_ls_wR_factor_ref         0.0884
_refine_ls_goodness_of_fit_ref   0.8837
_refine_ls_shift/su_max          0.0002956
_refine_ls_shift/su_mean         0.0000201


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        7435
_refine_ls_R_factor_all          0.0356
_refine_ls_wR_factor_all         0.0884

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                7304
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_gt          0.0880

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661-683 
_oxford_Hooft_y                  0.03(3) # for 3286 Friedel pairs 
_oxford_Bijvoet_difference       0.04(2) # for 3286 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          0.02(11) # for 3345 Friedel pairs 
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 3286 Friedel Pairs 
;

# choose from: 
# rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 1.58P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
F1 F 0.00143(9) 0.02511(18) 0.34143(7) 0.0422 1.0000 Uani . . . . . .
C2 C 0.02903(13) 0.1977(3) 0.32987(10) 0.0305 1.0000 Uani . . . . . .
C3 C -0.01735(11) 0.3470(3) 0.34920(10) 0.0244 1.0000 Uani . . . . . .
C4 C -0.09615(11) 0.3216(3) 0.38557(9) 0.0221 1.0000 Uani . . . . . .
C5 C -0.18024(12) 0.4214(3) 0.34497(10) 0.0243 1.0000 Uani . . . . . .
C6 C -0.22708(12) 0.3335(3) 0.27394(10) 0.0276 1.0000 Uani . . . . . .
O7 O -0.16863(8) 0.3455(2) 0.22207(7) 0.0255 1.0000 Uani . . . . . .
C8 C -0.20152(12) 0.2771(2) 0.15558(10) 0.0217 1.0000 Uani . . . . . .
O9 O -0.27591(9) 0.2143(2) 0.13708(7) 0.0338 1.0000 Uani . . . . . .
C10 C -0.13698(11) 0.2858(2) 0.10655(10) 0.0192 1.0000 Uani . . . . . .
C11 C -0.04888(12) 0.3410(2) 0.13051(9) 0.0196 1.0000 Uani . . . . . .
C12 C 0.00846(11) 0.3420(2) 0.08241(9) 0.0199 1.0000 Uani . . . . . .
C13 C -0.02118(11) 0.2922(2) 0.00882(9) 0.0193 1.0000 Uani . . . . . .
C14 C 0.03864(12) 0.2956(2) -0.04388(10) 0.0194 1.0000 Uani . . . . . .
C15 C 0.12792(11) 0.2407(2) -0.02239(9) 0.0197 1.0000 Uani . . . . . .
C16 C 0.18310(12) 0.2400(2) -0.07194(10) 0.0203 1.0000 Uani . . . . . .
C17 C 0.14936(12) 0.2967(2) -0.14297(10) 0.0205 1.0000 Uani . . . . . .
N18 N 0.20820(10) 0.2995(2) -0.19567(8) 0.0239 1.0000 Uani . . . . . .
O19 O 0.28372(9) 0.2386(2) -0.17591(8) 0.0366 1.0000 Uani . . . . . .
O20 O 0.17895(9) 0.3629(2) -0.25679(7) 0.0332 1.0000 Uani . . . . . .
C21 C 0.06202(12) 0.3534(2) -0.16627(10) 0.0220 1.0000 Uani . . . . . .
C22 C 0.00693(12) 0.3512(2) -0.11628(10) 0.0214 1.0000 Uani . . . . . .
C23 C -0.10983(11) 0.2372(2) -0.01461(9) 0.0201 1.0000 Uani . . . . . .
C24 C -0.16656(11) 0.2312(2) 0.03380(10) 0.0199 1.0000 Uani . . . . . .
C25 C -0.07066(13) 0.3847(3) 0.46629(10) 0.0273 1.0000 Uani . . . . . .
C26 C -0.13572(14) 0.3190(3) 0.51224(11) 0.0368 1.0000 Uani . . . . . .
C27 C 0.01483(14) 0.5224(3) 0.33609(11) 0.0330 1.0000 Uani . . . . . .
C28 C 0.08844(15) 0.5418(4) 0.30473(12) 0.0431 1.0000 Uani . . . . . .
C29 C 0.13196(14) 0.3884(4) 0.28569(11) 0.0470 1.0000 Uani . . . . . .
C30 C 0.10210(13) 0.2133(4) 0.29811(11) 0.0427 1.0000 Uani . . . . . .
O31 O 0.40644(8) 0.5952(2) 0.24855(7) 0.0259 1.0000 Uani . . . . . .
C32 C 0.35732(12) 0.5184(2) 0.18857(10) 0.0211 1.0000 Uani . . . . . .
O33 O 0.28382(9) 0.4566(2) 0.18504(7) 0.0346 1.0000 Uani . . . . . .
C34 C 0.40525(11) 0.5173(2) 0.12714(9) 0.0183 1.0000 Uani . . . . . .
C35 C 0.49502(12) 0.5649(2) 0.13737(10) 0.0200 1.0000 Uani . . . . . .
C36 C 0.53689(11) 0.5592(2) 0.07878(10) 0.0198 1.0000 Uani . . . . . .
C37 C 0.49054(11) 0.5125(2) 0.00869(9) 0.0178 1.0000 Uani . . . . . .
C38 C 0.53671(11) 0.5125(2) -0.05350(9) 0.0178 1.0000 Uani . . . . . .
C39 C 0.62673(11) 0.4609(2) -0.04135(10) 0.0198 1.0000 Uani . . . . . .
C40 C 0.67235(12) 0.4633(2) -0.09727(10) 0.0212 1.0000 Uani . . . . . .
C41 C 0.62786(12) 0.5162(2) -0.16650(10) 0.0213 1.0000 Uani . . . . . .
N42 N 0.67697(11) 0.5175(2) -0.22599(9) 0.0275 1.0000 Uani . . . . . .
O43 O 0.63785(10) 0.5678(2) -0.28704(8) 0.0384 1.0000 Uani . . . . . .
O44 O 0.75426(10) 0.4650(2) -0.21250(9) 0.0401 1.0000 Uani . . . . . .
C45 C 0.53847(12) 0.5654(3) -0.18119(10) 0.0229 1.0000 Uani . . . . . .
C46 C 0.49329(12) 0.5638(2) -0.12453(10) 0.0208 1.0000 Uani . . . . . .
C47 C 0.40005(11) 0.4672(2) -0.00140(9) 0.0183 1.0000 Uani . . . . . .
C48 C 0.35875(11) 0.4665(2) 0.05771(10) 0.0186 1.0000 Uani . . . . . .
C49 C 0.37315(12) 0.5886(3) 0.31608(10) 0.0249 1.0000 Uani . . . . . .
C50 C 0.45080(12) 0.6486(3) 0.37605(10) 0.0252 1.0000 Uani . . . . . .
C51 C 0.53358(12) 0.5241(3) 0.38312(10) 0.0247 1.0000 Uani . . . . . .
C52 C 0.61386(12) 0.6185(3) 0.43090(10) 0.0238 1.0000 Uani . . . . . .
C53 C 0.66866(13) 0.7314(3) 0.39982(10) 0.0280 1.0000 Uani . . . . . .
F54 F 0.64658(11) 0.7554(2) 0.32692(7) 0.0559 1.0000 Uani . . . . . .
C55 C 0.74256(14) 0.8224(3) 0.43994(12) 0.0338 1.0000 Uani . . . . . .
C56 C 0.76239(13) 0.8020(3) 0.51508(12) 0.0331 1.0000 Uani . . . . . .
C57 C 0.70885(13) 0.6924(3) 0.54853(11) 0.0329 1.0000 Uani . . . . . .
C58 C 0.63588(13) 0.6020(3) 0.50671(11) 0.0276 1.0000 Uani . . . . . .
C59 C 0.51627(13) 0.3300(3) 0.41069(13) 0.0361 1.0000 Uani . . . . . .
C60 C 0.59263(17) 0.1945(3) 0.41240(16) 0.0493 1.0000 Uani . . . . . .
H41 H -0.1102 0.1866 0.3866 0.0247 1.0000 Uiso R . . . . .
H52 H -0.2213 0.4335 0.3776 0.0286 1.0000 Uiso R . . . . .
H51 H -0.1631 0.5458 0.3344 0.0289 1.0000 Uiso R . . . . .
H62 H -0.2821 0.3968 0.2532 0.0345 1.0000 Uiso R . . . . .
H61 H -0.2412 0.2022 0.2803 0.0350 1.0000 Uiso R . . . . .
H111 H -0.0293 0.3831 0.1801 0.0217 1.0000 Uiso R . . . . .
H121 H 0.0703 0.3810 0.1001 0.0274 1.0000 Uiso R . . . . .
H151 H 0.1512 0.2027 0.0275 0.0242 1.0000 Uiso R . . . . .
H161 H 0.2446 0.2038 -0.0575 0.0246 1.0000 Uiso R . . . . .
H211 H 0.0418 0.3962 -0.2162 0.0281 1.0000 Uiso R . . . . .
H221 H -0.0534 0.3899 -0.1312 0.0264 1.0000 Uiso R . . . . .
H231 H -0.1320 0.2010 -0.0649 0.0243 1.0000 Uiso R . . . . .
H241 H -0.2274 0.1883 0.0180 0.0239 1.0000 Uiso R . . . . .
H251 H -0.0672 0.5143 0.4689 0.0358 1.0000 Uiso R . . . . .
H252 H -0.0129 0.3238 0.4868 0.0350 1.0000 Uiso R . . . . .
H261 H -0.1146 0.3446 0.5633 0.0527 1.0000 Uiso R . . . . .
H262 H -0.1941 0.3664 0.4942 0.0536 1.0000 Uiso R . . . . .
H263 H -0.1391 0.1904 0.5081 0.0535 1.0000 Uiso R . . . . .
H271 H -0.0167 0.6343 0.3471 0.0445 1.0000 Uiso R . . . . .
H281 H 0.1084 0.6671 0.2967 0.0519 1.0000 Uiso R . . . . .
H291 H 0.1796 0.3916 0.2641 0.0516 1.0000 Uiso R . . . . .
H301 H 0.1303 0.1131 0.2853 0.0563 1.0000 Uiso R . . . . .
H351 H 0.5274 0.6042 0.1835 0.0224 1.0000 Uiso R . . . . .
H361 H 0.5977 0.5914 0.0870 0.0246 1.0000 Uiso R . . . . .
H391 H 0.6555 0.4204 0.0066 0.0254 1.0000 Uiso R . . . . .
H401 H 0.7341 0.4296 -0.0887 0.0247 1.0000 Uiso R . . . . .
H451 H 0.5086 0.5975 -0.2295 0.0287 1.0000 Uiso R . . . . .
H461 H 0.4328 0.6021 -0.1347 0.0258 1.0000 Uiso R . . . . .
H471 H 0.3658 0.4301 -0.0488 0.0216 1.0000 Uiso R . . . . .
H481 H 0.2976 0.4261 0.0502 0.0250 1.0000 Uiso R . . . . .
H492 H 0.3218 0.6769 0.3104 0.0335 1.0000 Uiso R . . . . .
H491 H 0.3572 0.4627 0.3245 0.0350 1.0000 Uiso R . . . . .
H501 H 0.4660 0.7754 0.3646 0.0300 1.0000 Uiso R . . . . .
H502 H 0.4289 0.6398 0.4228 0.0299 1.0000 Uiso R . . . . .
H511 H 0.5442 0.5127 0.3333 0.0301 1.0000 Uiso R . . . . .
H551 H 0.7777 0.8991 0.4152 0.0417 1.0000 Uiso R . . . . .
H561 H 0.8133 0.8565 0.5443 0.0393 1.0000 Uiso R . . . . .
H571 H 0.7231 0.6796 0.5999 0.0398 1.0000 Uiso R . . . . .
H581 H 0.5921 0.5233 0.5315 0.0278 1.0000 Uiso R . . . . .
H592 H 0.5011 0.3427 0.4588 0.0476 1.0000 Uiso R . . . . .
H591 H 0.4621 0.2837 0.3756 0.0465 1.0000 Uiso R . . . . .
H602 H 0.5747 0.0714 0.4256 0.0687 1.0000 Uiso R . . . . .
H601 H 0.6452 0.2325 0.4480 0.0700 1.0000 Uiso R . . . . .
H603 H 0.6063 0.1870 0.3653 0.0690 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.12351(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 . C2 . 1.349(3) yes
C2 . C3 . 1.383(3) yes
C2 . C30 . 1.381(3) yes
C3 . C4 . 1.520(2) yes
C3 . C27 . 1.401(3) yes
C4 . C5 . 1.535(2) yes
C4 . C25 . 1.544(2) yes
C4 . H41 . 1.000 no
C5 . C6 . 1.510(3) yes
C5 . H52 . 0.969 no
C5 . H51 . 0.968 no
C6 . O7 . 1.456(2) yes
C6 . H62 . 0.969 no
C6 . H61 . 0.986 no
O7 . C8 . 1.333(2) yes
C8 . O9 . 1.212(2) yes
C8 . C10 . 1.487(2) yes
C10 . C11 . 1.393(2) yes
C10 . C24 . 1.395(2) yes
C11 . C12 . 1.385(2) yes
C11 . H111 . 0.960 no
C12 . C13 . 1.401(2) yes
C12 . H121 . 0.981 no
C13 . C14 . 1.482(2) yes
C13 . C23 . 1.399(2) yes
C14 . C15 . 1.405(2) yes
C14 . C22 . 1.396(2) yes
C15 . C16 . 1.381(3) yes
C15 . H151 . 0.966 no
C16 . C17 . 1.381(2) yes
C16 . H161 . 0.964 no
C17 . N18 . 1.471(2) yes
C17 . C21 . 1.385(3) yes
N18 . O19 . 1.225(2) yes
N18 . O20 . 1.224(2) yes
C21 . C22 . 1.386(2) yes
C21 . H211 . 0.968 no
C22 . H221 . 0.953 no
C23 . C24 . 1.383(2) yes
C23 . H231 . 0.965 no
C24 . H241 . 0.971 no
C25 . C26 . 1.524(3) yes
C25 . H251 . 0.939 no
C25 . H252 . 0.994 no
C26 . H261 . 0.959 no
C26 . H262 . 0.955 no
C26 . H263 . 0.933 no
C27 . C28 . 1.387(3) yes
C27 . H271 . 0.986 no
C28 . C29 . 1.379(4) yes
C28 . H281 . 0.978 no
C29 . C30 . 1.382(4) yes
C29 . H291 . 0.908 no
C30 . H301 . 0.901 no
O31 . C32 . 1.333(2) yes
O31 . C49 . 1.458(2) yes
C32 . O33 . 1.205(2) yes
C32 . C34 . 1.488(2) yes
C34 . C35 . 1.397(2) yes
C34 . C48 . 1.392(2) yes
C35 . C36 . 1.382(2) yes
C35 . H351 . 0.943 no
C36 . C37 . 1.394(2) yes
C36 . H361 . 0.945 no
C37 . C38 . 1.483(2) yes
C37 . C47 . 1.404(2) yes
C38 . C39 . 1.406(2) yes
C38 . C46 . 1.403(2) yes
C39 . C40 . 1.375(2) yes
C39 . H391 . 0.958 no
C40 . C41 . 1.383(3) yes
C40 . H401 . 0.961 no
C41 . N42 . 1.469(2) yes
C41 . C45 . 1.391(3) yes
N42 . O43 . 1.227(2) yes
N42 . O44 . 1.223(2) yes
C45 . C46 . 1.382(3) yes
C45 . H451 . 0.951 no
C46 . H461 . 0.952 no
C47 . C48 . 1.384(2) yes
C47 . H471 . 0.969 no
C48 . H481 . 0.967 no
C49 . C50 . 1.519(3) yes
C49 . H492 . 1.003 no
C49 . H491 . 0.964 no
C50 . C51 . 1.542(3) yes
C50 . H501 . 0.980 no
C50 . H502 . 1.001 no
C51 . C52 . 1.524(3) yes
C51 . C59 . 1.536(3) yes
C51 . H511 . 0.980 no
C52 . C53 . 1.385(3) yes
C52 . C58 . 1.389(3) yes
C53 . F54 . 1.343(2) yes
C53 . C55 . 1.389(3) yes
C55 . C56 . 1.379(3) yes
C55 . H551 . 0.959 no
C56 . C57 . 1.383(3) yes
C56 . H561 . 0.941 no
C57 . C58 . 1.388(3) yes
C57 . H571 . 0.941 no
C58 . H581 . 1.058 no
C59 . C60 . 1.524(3) yes
C59 . H592 . 0.979 no
C59 . H591 . 1.003 no
C60 . H602 . 0.978 no
C60 . H601 . 0.972 no
C60 . H603 . 0.947 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F1 . C2 . C3 . 118.85(17) yes
F1 . C2 . C30 . 117.1(2) yes
C3 . C2 . C30 . 124.0(2) yes
C2 . C3 . C4 . 121.75(18) yes
C2 . C3 . C27 . 116.08(18) yes
C4 . C3 . C27 . 122.12(18) yes
C3 . C4 . C5 . 113.03(15) yes
C3 . C4 . C25 . 109.73(14) yes
C5 . C4 . C25 . 110.99(15) yes
C3 . C4 . H41 . 108.8 no
C5 . C4 . H41 . 107.7 no
C25 . C4 . H41 . 106.3 no
C4 . C5 . C6 . 115.66(16) yes
C4 . C5 . H52 . 108.9 no
C6 . C5 . H52 . 109.7 no
C4 . C5 . H51 . 107.4 no
C6 . C5 . H51 . 108.2 no
H52 . C5 . H51 . 106.6 no
C5 . C6 . O7 . 108.15(14) yes
C5 . C6 . H62 . 111.6 no
O7 . C6 . H62 . 108.4 no
C5 . C6 . H61 . 112.1 no
O7 . C6 . H61 . 108.6 no
H62 . C6 . H61 . 107.9 no
C6 . O7 . C8 . 115.50(14) yes
O7 . C8 . O9 . 123.72(17) yes
O7 . C8 . C10 . 112.69(14) yes
O9 . C8 . C10 . 123.59(16) yes
C8 . C10 . C11 . 123.01(16) yes
C8 . C10 . C24 . 117.64(15) yes
C11 . C10 . C24 . 119.33(16) yes
C10 . C11 . C12 . 120.16(16) yes
C10 . C11 . H111 . 119.1 no
C12 . C11 . H111 . 120.6 no
C11 . C12 . C13 . 120.95(16) yes
C11 . C12 . H121 . 119.2 no
C13 . C12 . H121 . 119.8 no
C12 . C13 . C14 . 121.82(15) yes
C12 . C13 . C23 . 118.33(16) yes
C14 . C13 . C23 . 119.85(16) yes
C13 . C14 . C15 . 120.79(16) yes
C13 . C14 . C22 . 120.54(16) yes
C15 . C14 . C22 . 118.66(16) yes
C14 . C15 . C16 . 120.77(16) yes
C14 . C15 . H151 . 119.9 no
C16 . C15 . H151 . 119.3 no
C15 . C16 . C17 . 118.83(16) yes
C15 . C16 . H161 . 121.3 no
C17 . C16 . H161 . 119.9 no
C16 . C17 . N18 . 119.13(15) yes
C16 . C17 . C21 . 122.27(16) yes
N18 . C17 . C21 . 118.60(15) yes
C17 . N18 . O19 . 118.15(15) yes
C17 . N18 . O20 . 118.14(15) yes
O19 . N18 . O20 . 123.71(16) yes
C17 . C21 . C22 . 118.37(16) yes
C17 . C21 . H211 . 119.4 no
C22 . C21 . H211 . 122.2 no
C14 . C22 . C21 . 121.09(16) yes
C14 . C22 . H221 . 119.2 no
C21 . C22 . H221 . 119.7 no
C13 . C23 . C24 . 120.82(16) yes
C13 . C23 . H231 . 120.2 no
C24 . C23 . H231 . 119.0 no
C10 . C24 . C23 . 120.36(15) yes
C10 . C24 . H241 . 118.9 no
C23 . C24 . H241 . 120.8 no
C4 . C25 . C26 . 113.30(15) yes
C4 . C25 . H251 . 110.2 no
C26 . C25 . H251 . 108.6 no
C4 . C25 . H252 . 105.6 no
C26 . C25 . H252 . 106.6 no
H251 . C25 . H252 . 112.6 no
C25 . C26 . H261 . 112.0 no
C25 . C26 . H262 . 111.8 no
H261 . C26 . H262 . 112.2 no
C25 . C26 . H263 . 107.2 no
H261 . C26 . H263 . 106.0 no
H262 . C26 . H263 . 107.2 no
C3 . C27 . C28 . 121.0(2) yes
C3 . C27 . H271 . 119.9 no
C28 . C27 . H271 . 119.1 no
C27 . C28 . C29 . 120.8(2) yes
C27 . C28 . H281 . 118.0 no
C29 . C28 . H281 . 121.3 no
C28 . C29 . C30 . 119.73(19) yes
C28 . C29 . H291 . 125.1 no
C30 . C29 . H291 . 115.2 no
C29 . C30 . C2 . 118.4(2) yes
C29 . C30 . H301 . 119.7 no
C2 . C30 . H301 . 121.9 no
C32 . O31 . C49 . 118.20(14) yes
O31 . C32 . O33 . 124.07(17) yes
O31 . C32 . C34 . 111.36(15) yes
O33 . C32 . C34 . 124.56(16) yes
C32 . C34 . C35 . 121.96(15) yes
C32 . C34 . C48 . 118.57(15) yes
C35 . C34 . C48 . 119.47(16) yes
C34 . C35 . C36 . 119.79(16) yes
C34 . C35 . H351 . 121.1 no
C36 . C35 . H351 . 119.1 no
C35 . C36 . C37 . 121.24(16) yes
C35 . C36 . H361 . 118.4 no
C37 . C36 . H361 . 120.4 no
C36 . C37 . C38 . 120.01(15) yes
C36 . C37 . C47 . 118.67(15) yes
C38 . C37 . C47 . 121.33(15) yes
C37 . C38 . C39 . 119.43(15) yes
C37 . C38 . C46 . 121.91(15) yes
C39 . C38 . C46 . 118.66(16) yes
C38 . C39 . C40 . 121.13(16) yes
C38 . C39 . H391 . 118.5 no
C40 . C39 . H391 . 120.3 no
C39 . C40 . C41 . 118.78(16) yes
C39 . C40 . H401 . 121.0 no
C41 . C40 . H401 . 120.3 no
C40 . C41 . N42 . 118.43(16) yes
C40 . C41 . C45 . 121.98(16) yes
N42 . C41 . C45 . 119.58(16) yes
C41 . N42 . O43 . 118.33(15) yes
C41 . N42 . O44 . 118.34(15) yes
O43 . N42 . O44 . 123.31(16) yes
C41 . C45 . C46 . 118.83(16) yes
C41 . C45 . H451 . 120.7 no
C46 . C45 . H451 . 120.5 no
C38 . C46 . C45 . 120.61(16) yes
C38 . C46 . H461 . 121.1 no
C45 . C46 . H461 . 118.3 no
C37 . C47 . C48 . 120.17(16) yes
C37 . C47 . H471 . 121.4 no
C48 . C47 . H471 . 118.4 no
C34 . C48 . C47 . 120.61(16) yes
C34 . C48 . H481 . 120.6 no
C47 . C48 . H481 . 118.8 no
O31 . C49 . C50 . 105.26(14) yes
O31 . C49 . H492 . 107.4 no
C50 . C49 . H492 . 112.1 no
O31 . C49 . H491 . 108.7 no
C50 . C49 . H491 . 109.6 no
H492 . C49 . H491 . 113.3 no
C49 . C50 . C51 . 113.83(15) yes
C49 . C50 . H501 . 107.1 no
C51 . C50 . H501 . 109.5 no
C49 . C50 . H502 . 105.5 no
C51 . C50 . H502 . 108.2 no
H501 . C50 . H502 . 112.9 no
C50 . C51 . C52 . 109.98(15) yes
C50 . C51 . C59 . 111.29(16) yes
C52 . C51 . C59 . 112.88(16) yes
C50 . C51 . H511 . 105.4 no
C52 . C51 . H511 . 108.5 no
C59 . C51 . H511 . 108.5 no
C51 . C52 . C53 . 120.53(17) yes
C51 . C52 . C58 . 123.49(17) yes
C53 . C52 . C58 . 115.96(17) yes
C52 . C53 . F54 . 116.99(17) yes
C52 . C53 . C55 . 123.67(18) yes
F54 . C53 . C55 . 119.32(18) yes
C53 . C55 . C56 . 118.62(19) yes
C53 . C55 . H551 . 119.6 no
C56 . C55 . H551 . 121.7 no
C55 . C56 . C57 . 119.67(18) yes
C55 . C56 . H561 . 121.6 no
C57 . C56 . H561 . 118.7 no
C56 . C57 . C58 . 120.23(19) yes
C56 . C57 . H571 . 118.8 no
C58 . C57 . H571 . 120.9 no
C52 . C58 . C57 . 121.84(19) yes
C52 . C58 . H581 . 116.7 no
C57 . C58 . H581 . 121.4 no
C51 . C59 . C60 . 113.96(18) yes
C51 . C59 . H592 . 108.3 no
C60 . C59 . H592 . 111.8 no
C51 . C59 . H591 . 105.3 no
C60 . C59 . H591 . 109.3 no
H592 . C59 . H591 . 107.7 no
C59 . C60 . H602 . 109.4 no
C59 . C60 . H601 . 111.0 no
H602 . C60 . H601 . 108.9 no
C59 . C60 . H603 . 109.7 no
H602 . C60 . H603 . 108.1 no
H601 . C60 . H603 . 109.6 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C29 . H291 . O33 . 165 0.91 2.44 3.328(3) yes
C36 . H361 . O19 2_655 142 0.95 2.44 3.237(3) yes
C46 . H461 . O9 2_555 170 0.95 2.54 3.477(3) yes
C59 . H591 . O43 2_645 159 1.00 2.54 3.498(3) yes


# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
