# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# 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_RT-L4F_in_P-1
_database_code_depnum_ccdc_archive 'CCDC 1451433'
_audit_update_record             
;
2016-02-02 deposited with the CCDC.
2016-12-09 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C27 H21 F N4 O2'
_chemical_formula_moiety         'C27 H21 F N4 O2'
_chemical_formula_weight         452.49
_chemical_melting_point          467.15-469.15

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.4863(6)
_cell_length_b                   10.0848(6)
_cell_length_c                   13.3834(9)
_cell_angle_alpha                110.202(3)
_cell_angle_beta                 91.710(3)
_cell_angle_gamma                112.977(2)
_cell_volume                     1085.98(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10121
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      27.56
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.320
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472.00
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_correction_T_max  0.970

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku SCX mini'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 6.849
_diffrn_reflns_number            11036
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             4940
_reflns_number_gt                4252
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1289
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4940
_refine_ls_number_parameters     307
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0679P)²+0.2919P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.230
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
C C 0.0033 0.0016
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.24063(15) -0.32030(18) 0.33053(16) 0.1207(6) Uani 1.0 2 d . . .
O1 O 0.53518(16) 0.40546(14) 0.59710(9) 0.0678(4) Uani 1.0 2 d . . .
O2 O 0.4712(2) 0.16442(17) 0.56563(9) 0.0800(5) Uani 1.0 2 d . . .
N1 N 0.59960(13) 0.18663(12) 0.27287(9) 0.0358(3) Uani 1.0 2 d . . .
N2 N 0.30587(14) 0.22535(13) 0.21070(9) 0.0382(3) Uani 1.0 2 d . . .
N3 N 0.23025(13) 0.02388(14) -0.01488(9) 0.0392(3) Uani 1.0 2 d . . .
N4 N 0.48907(15) 0.26960(15) 0.53571(9) 0.0462(3) Uani 1.0 2 d . . .
C1 C 0.43765(14) 0.06272(14) 0.23801(9) 0.0315(3) Uani 1.0 2 d . . .
C2 C 0.38615(14) 0.05975(14) 0.34710(9) 0.0315(3) Uani 1.0 2 d . . .
C3 C 0.45437(15) 0.23382(15) 0.41690(10) 0.0355(3) Uani 1.0 2 d . . .
C4 C 0.60465(17) 0.31032(16) 0.37450(11) 0.0420(3) Uani 1.0 2 d . . .
C5 C 0.7636(2) 0.3669(3) 0.44507(15) 0.0682(6) Uani 1.0 2 d . . .
C6 C 0.85242(18) 0.2958(2) 0.36828(15) 0.0587(5) Uani 1.0 2 d . . .
C7 C 0.72450(16) 0.14168(18) 0.29349(13) 0.0471(4) Uani 1.0 2 d . . .
C8 C 0.42317(15) -0.09117(14) 0.15316(10) 0.0331(3) Uani 1.0 2 d . . .
C9 C 0.46929(17) -0.20039(16) 0.16511(11) 0.0415(3) Uani 1.0 2 d . . .
C10 C 0.44771(19) -0.33074(18) 0.07401(13) 0.0495(4) Uani 1.0 2 d . . .
C11 C 0.38169(19) -0.35252(17) -0.02764(12) 0.0502(4) Uani 1.0 2 d . . .
C12 C 0.33186(17) -0.24739(16) -0.04053(11) 0.0433(3) Uani 1.0 2 d . . .
C13 C 0.35185(14) -0.11714(15) 0.05060(10) 0.0337(3) Uani 1.0 2 d . . .
C14 C 0.30312(14) 0.00676(14) 0.06097(10) 0.0327(3) Uani 1.0 2 d . . .
C15 C 0.34342(14) 0.10899(14) 0.17270(9) 0.0317(3) Uani 1.0 2 d . . .
C16 C 0.22613(16) 0.24640(16) 0.13338(11) 0.0382(3) Uani 1.0 2 d . . .
C17 C 0.1786(2) 0.36813(19) 0.16624(14) 0.0524(4) Uani 1.0 2 d . . .
C18 C 0.1006(2) 0.3917(2) 0.09096(16) 0.0594(5) Uani 1.0 2 d . . .
C19 C 0.0675(2) 0.2955(2) -0.01898(15) 0.0582(5) Uani 1.0 2 d . . .
C20 C 0.11164(18) 0.1765(2) -0.05323(13) 0.0510(4) Uani 1.0 2 d . . .
C21 C 0.19163(15) 0.14794(16) 0.02203(11) 0.0384(3) Uani 1.0 2 d . . .
C22 C 0.21627(15) -0.03770(15) 0.34218(10) 0.0358(3) Uani 1.0 2 d . . .
C23 C 0.10429(18) 0.02005(19) 0.35613(13) 0.0493(4) Uani 1.0 2 d . . .
C24 C -0.0495(2) -0.0745(3) 0.35304(17) 0.0636(5) Uani 1.0 2 d . . .
C25 C -0.0902(2) -0.2268(3) 0.33410(18) 0.0694(5) Uani 1.0 2 d . . .
C26 C 0.0152(3) -0.2895(3) 0.3189(2) 0.0777(6) Uani 1.0 2 d . . .
C27 C 0.1683(2) -0.19403(19) 0.32378(15) 0.0566(4) Uani 1.0 2 d . . .
H2 H 0.4459 0.0167 0.3765 0.0378 Uiso 1.0 2 calc R . .
H3 H 0.3799 0.2745 0.4045 0.0425 Uiso 1.0 2 calc R . .
H4 H 0.6008 0.3967 0.3584 0.0504 Uiso 1.0 2 calc R . .
H5A H 0.8174 0.4801 0.4750 0.0818 Uiso 1.0 2 calc R . .
H5B H 0.7510 0.3310 0.5041 0.0818 Uiso 1.0 2 calc R . .
H6A H 0.9035 0.3603 0.3289 0.0704 Uiso 1.0 2 calc R . .
H6B H 0.9296 0.2809 0.4067 0.0704 Uiso 1.0 2 calc R . .
H7A H 0.7572 0.0972 0.2269 0.0565 Uiso 1.0 2 calc R . .
H7B H 0.6916 0.0674 0.3282 0.0565 Uiso 1.0 2 calc R . .
H9 H 0.5138 -0.1865 0.2329 0.0498 Uiso 1.0 2 calc R . .
H10 H 0.4780 -0.4048 0.0812 0.0594 Uiso 1.0 2 calc R . .
H11 H 0.3710 -0.4394 -0.0878 0.0602 Uiso 1.0 2 calc R . .
H12 H 0.2859 -0.2630 -0.1085 0.0519 Uiso 1.0 2 calc R . .
H17 H 0.2001 0.4328 0.2392 0.0629 Uiso 1.0 2 calc R . .
H18 H 0.0694 0.4725 0.1132 0.0713 Uiso 1.0 2 calc R . .
H19 H 0.0148 0.3130 -0.0692 0.0698 Uiso 1.0 2 calc R . .
H20 H 0.0891 0.1135 -0.1266 0.0611 Uiso 1.0 2 calc R . .
H23 H 0.1329 0.1243 0.3678 0.0592 Uiso 1.0 2 calc R . .
H24 H -0.1234 -0.0342 0.3638 0.0763 Uiso 1.0 2 calc R . .
H26 H -0.0156 -0.3946 0.3054 0.0932 Uiso 1.0 2 calc R . .
H27 H 0.2412 -0.2356 0.3145 0.0680 Uiso 1.0 2 calc R . .



#==============================================================================
_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
F1 C25 1.357(3) yes . .
O1 N4 1.2152(17) yes . .
O2 N4 1.213(3) yes . .
N1 C1 1.4816(14) yes . .
N1 C4 1.4785(18) yes . .
N1 C7 1.474(3) yes . .
N2 C15 1.299(2) yes . .
N2 C16 1.385(3) yes . .
N3 C14 1.308(3) yes . .
N3 C21 1.373(3) yes . .
N4 C3 1.4989(19) yes . .
C1 C2 1.5597(18) yes . .
C1 C8 1.5245(18) yes . .
C1 C15 1.530(3) yes . .
C2 C3 1.5223(17) yes . .
C2 C22 1.5099(17) yes . .
C3 C4 1.563(2) yes . .
C4 C5 1.537(3) yes . .
C5 C6 1.515(3) yes . .
C6 C7 1.5070(18) yes . .
C8 C9 1.387(3) yes . .
C8 C13 1.403(2) yes . .
C9 C10 1.387(2) yes . .
C10 C11 1.388(3) yes . .
C11 C12 1.375(3) yes . .
C12 C13 1.3907(18) yes . .
C13 C14 1.459(3) yes . .
C14 C15 1.4277(16) yes . .
C16 C17 1.405(3) yes . .
C16 C21 1.4174(18) yes . .
C17 C18 1.370(4) yes . .
C18 C19 1.398(3) yes . .
C19 C20 1.360(3) yes . .
C20 C21 1.414(3) yes . .
C22 C23 1.386(3) yes . .
C22 C27 1.385(3) yes . .
C23 C24 1.387(3) yes . .
C24 C25 1.354(4) yes . .
C25 C26 1.362(4) yes . .
C26 C27 1.378(3) yes . .
C2 H2 0.980 no . .
C3 H3 0.980 no . .
C4 H4 0.980 no . .
C5 H5A 0.970 no . .
C5 H5B 0.970 no . .
C6 H6A 0.970 no . .
C6 H6B 0.970 no . .
C7 H7A 0.970 no . .
C7 H7B 0.970 no . .
C9 H9 0.930 no . .
C10 H10 0.930 no . .
C11 H11 0.930 no . .
C12 H12 0.930 no . .
C17 H17 0.930 no . .
C18 H18 0.930 no . .
C19 H19 0.930 no . .
C20 H20 0.930 no . .
C23 H23 0.930 no . .
C24 H24 0.930 no . .
C26 H26 0.930 no . .
C27 H27 0.930 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 N1 C4 107.11(11) yes . . .
C1 N1 C7 117.30(12) yes . . .
C4 N1 C7 107.53(12) yes . . .
C15 N2 C16 114.66(11) yes . . .
C14 N3 C21 114.28(12) yes . . .
O1 N4 O2 123.63(14) yes . . .
O1 N4 C3 116.88(15) yes . . .
O2 N4 C3 119.49(12) yes . . .
N1 C1 C2 103.41(9) yes . . .
N1 C1 C8 113.16(12) yes . . .
N1 C1 C15 107.65(12) yes . . .
C2 C1 C8 117.06(12) yes . . .
C2 C1 C15 114.59(12) yes . . .
C8 C1 C15 100.99(10) yes . . .
C1 C2 C3 100.86(11) yes . . .
C1 C2 C22 117.26(10) yes . . .
C3 C2 C22 117.85(12) yes . . .
N4 C3 C2 113.09(13) yes . . .
N4 C3 C4 111.80(10) yes . . .
C2 C3 C4 105.64(11) yes . . .
N1 C4 C3 105.69(10) yes . . .
N1 C4 C5 104.97(15) yes . . .
C3 C4 C5 118.01(15) yes . . .
C4 C5 C6 104.52(13) yes . . .
C5 C6 C7 102.15(13) yes . . .
N1 C7 C6 102.17(15) yes . . .
C1 C8 C9 129.43(13) yes . . .
C1 C8 C13 111.02(14) yes . . .
C9 C8 C13 119.55(12) yes . . .
C8 C9 C10 118.75(15) yes . . .
C9 C10 C11 121.13(19) yes . . .
C10 C11 C12 120.87(14) yes . . .
C11 C12 C13 118.30(15) yes . . .
C8 C13 C12 121.34(16) yes . . .
C8 C13 C14 109.00(11) yes . . .
C12 C13 C14 129.63(14) yes . . .
N3 C14 C13 128.24(11) yes . . .
N3 C14 C15 123.74(15) yes . . .
C13 C14 C15 107.98(13) yes . . .
N2 C15 C1 126.14(11) yes . . .
N2 C15 C14 123.56(15) yes . . .
C1 C15 C14 110.29(13) yes . . .
N2 C16 C17 119.18(13) yes . . .
N2 C16 C21 121.42(16) yes . . .
C17 C16 C21 119.40(17) yes . . .
C16 C17 C18 120.13(16) yes . . .
C17 C18 C19 120.5(2) yes . . .
C18 C19 C20 120.7(3) yes . . .
C19 C20 C21 120.44(15) yes . . .
N3 C21 C16 122.26(16) yes . . .
N3 C21 C20 118.93(13) yes . . .
C16 C21 C20 118.79(16) yes . . .
C2 C22 C23 123.97(14) yes . . .
C2 C22 C27 118.58(16) yes . . .
C23 C22 C27 117.45(14) yes . . .
C22 C23 C24 121.33(19) yes . . .
C23 C24 C25 118.7(3) yes . . .
F1 C25 C24 119.1(3) yes . . .
F1 C25 C26 118.7(3) yes . . .
C24 C25 C26 122.19(18) yes . . .
C25 C26 C27 118.7(2) yes . . .
C22 C27 C26 121.6(2) yes . . .
C1 C2 H2 106.669 no . . .
C3 C2 H2 106.671 no . . .
C22 C2 H2 106.666 no . . .
N4 C3 H3 108.728 no . . .
C2 C3 H3 108.725 no . . .
C4 C3 H3 108.728 no . . .
N1 C4 H4 109.262 no . . .
C3 C4 H4 109.264 no . . .
C5 C4 H4 109.274 no . . .
C4 C5 H5A 110.842 no . . .
C4 C5 H5B 110.845 no . . .
C6 C5 H5A 110.850 no . . .
C6 C5 H5B 110.853 no . . .
H5A C5 H5B 108.896 no . . .
C5 C6 H6A 111.339 no . . .
C5 C6 H6B 111.335 no . . .
C7 C6 H6A 111.339 no . . .
C7 C6 H6B 111.336 no . . .
H6A C6 H6B 109.220 no . . .
N1 C7 H7A 111.328 no . . .
N1 C7 H7B 111.336 no . . .
C6 C7 H7A 111.334 no . . .
C6 C7 H7B 111.339 no . . .
H7A C7 H7B 109.218 no . . .
C8 C9 H9 120.627 no . . .
C10 C9 H9 120.620 no . . .
C9 C10 H10 119.434 no . . .
C11 C10 H10 119.434 no . . .
C10 C11 H11 119.564 no . . .
C12 C11 H11 119.565 no . . .
C11 C12 H12 120.855 no . . .
C13 C12 H12 120.846 no . . .
C16 C17 H17 119.935 no . . .
C18 C17 H17 119.939 no . . .
C17 C18 H18 119.729 no . . .
C19 C18 H18 119.722 no . . .
C18 C19 H19 119.653 no . . .
C20 C19 H19 119.654 no . . .
C19 C20 H20 119.782 no . . .
C21 C20 H20 119.781 no . . .
C22 C23 H23 119.338 no . . .
C24 C23 H23 119.334 no . . .
C23 C24 H24 120.643 no . . .
C25 C24 H24 120.643 no . . .
C25 C26 H26 120.646 no . . .
C27 C26 H26 120.646 no . . .
C22 C27 H27 119.207 no . . .
C26 C27 H27 119.193 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 N1 C4 C3 16.51(17) no . . . .
C1 N1 C4 C5 141.96(12) no . . . .
C4 N1 C1 C2 -36.48(15) no . . . .
C4 N1 C1 C8 -164.12(12) no . . . .
C4 N1 C1 C15 85.17(13) no . . . .
C1 N1 C7 C6 -157.24(10) no . . . .
C7 N1 C1 C2 84.42(14) no . . . .
C7 N1 C1 C8 -43.22(16) no . . . .
C7 N1 C1 C15 -153.94(11) no . . . .
C4 N1 C7 C6 -36.56(15) no . . . .
C7 N1 C4 C3 -110.39(13) no . . . .
C7 N1 C4 C5 15.06(15) no . . . .
C15 N2 C16 C17 179.30(11) no . . . .
C15 N2 C16 C21 -0.72(18) no . . . .
C16 N2 C15 C1 177.10(11) no . . . .
C16 N2 C15 C14 -1.70(18) no . . . .
C14 N3 C21 C16 -1.06(17) no . . . .
C14 N3 C21 C20 -179.63(11) no . . . .
C21 N3 C14 C13 176.02(11) no . . . .
C21 N3 C14 C15 -1.37(17) no . . . .
O1 N4 C3 C2 -175.77(13) no . . . .
O1 N4 C3 C4 65.14(19) no . . . .
O2 N4 C3 C2 4.7(2) no . . . .
O2 N4 C3 C4 -114.43(17) no . . . .
N1 C1 C2 C3 41.41(14) no . . . .
N1 C1 C2 C22 170.76(12) no . . . .
N1 C1 C8 C9 73.03(17) no . . . .
N1 C1 C8 C13 -106.94(13) no . . . .
N1 C1 C15 N2 -68.47(15) no . . . .
N1 C1 C15 C14 110.46(10) no . . . .
C2 C1 C8 C9 -47.09(18) no . . . .
C2 C1 C8 C13 132.94(12) no . . . .
C8 C1 C2 C3 166.57(11) no . . . .
C8 C1 C2 C22 -64.08(17) no . . . .
C2 C1 C15 N2 45.94(15) no . . . .
C2 C1 C15 C14 -135.14(9) no . . . .
C15 C1 C2 C3 -75.45(10) no . . . .
C15 C1 C2 C22 53.90(15) no . . . .
C8 C1 C15 N2 172.70(11) no . . . .
C8 C1 C15 C14 -8.37(12) no . . . .
C15 C1 C8 C9 -172.20(12) no . . . .
C15 C1 C8 C13 7.83(13) no . . . .
C1 C2 C3 N4 -153.69(11) no . . . .
C1 C2 C3 C4 -31.11(14) no . . . .
C1 C2 C22 C23 -92.76(15) no . . . .
C1 C2 C22 C27 87.94(17) no . . . .
C3 C2 C22 C23 28.04(19) no . . . .
C3 C2 C22 C27 -151.26(12) no . . . .
C22 C2 C3 N4 77.35(16) no . . . .
C22 C2 C3 C4 -160.07(12) no . . . .
N4 C3 C4 N1 133.71(13) no . . . .
N4 C3 C4 C5 16.76(19) no . . . .
C2 C3 C4 N1 10.31(17) no . . . .
C2 C3 C4 C5 -106.64(13) no . . . .
N1 C4 C5 C6 12.25(18) no . . . .
C3 C4 C5 C6 129.59(14) no . . . .
C4 C5 C6 C7 -34.1(2) no . . . .
C5 C6 C7 N1 43.1(2) no . . . .
C1 C8 C9 C10 -178.01(11) no . . . .
C1 C8 C13 C12 177.38(10) no . . . .
C1 C8 C13 C14 -4.66(14) no . . . .
C9 C8 C13 C12 -2.59(19) no . . . .
C9 C8 C13 C14 175.37(11) no . . . .
C13 C8 C9 C10 1.96(19) no . . . .
C8 C9 C10 C11 0.2(3) no . . . .
C9 C10 C11 C12 -1.8(3) no . . . .
C10 C11 C12 C13 1.1(3) no . . . .
C11 C12 C13 C8 1.0(2) no . . . .
C11 C12 C13 C14 -176.48(12) no . . . .
C8 C13 C14 N3 -178.69(11) no . . . .
C8 C13 C14 C15 -0.97(13) no . . . .
C12 C13 C14 N3 -1.0(3) no . . . .
C12 C13 C14 C15 176.77(13) no . . . .
N3 C14 C15 N2 2.99(19) no . . . .
N3 C14 C15 C1 -175.98(11) no . . . .
C13 C14 C15 N2 -174.86(10) no . . . .
C13 C14 C15 C1 6.18(13) no . . . .
N2 C16 C17 C18 179.50(12) no . . . .
N2 C16 C21 N3 2.2(2) no . . . .
N2 C16 C21 C20 -179.20(11) no . . . .
C17 C16 C21 N3 -177.80(12) no . . . .
C17 C16 C21 C20 0.78(19) no . . . .
C21 C16 C17 C18 -0.5(3) no . . . .
C16 C17 C18 C19 -0.0(3) no . . . .
C17 C18 C19 C20 0.2(3) no . . . .
C18 C19 C20 C21 0.1(3) no . . . .
C19 C20 C21 N3 178.01(14) no . . . .
C19 C20 C21 C16 -0.6(2) no . . . .
C2 C22 C23 C24 -178.58(12) no . . . .
C2 C22 C27 C26 179.67(13) no . . . .
C23 C22 C27 C26 0.3(3) no . . . .
C27 C22 C23 C24 0.7(3) no . . . .
C22 C23 C24 C25 -1.1(3) no . . . .
C23 C24 C25 F1 -179.75(18) no . . . .
C23 C24 C25 C26 0.5(4) no . . . .
F1 C25 C26 C27 -179.2(2) no . . . .
C24 C25 C26 C27 0.5(4) no . . . .
C25 C26 C27 C22 -0.9(4) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
F1 C23 3.600(2) no . .
F1 C27 3.595(3) no . .
O1 C4 2.978(2) no . .
O1 C5 3.059(3) no . .
O2 C2 2.7168(17) no . .
O2 C4 3.413(3) no . .
O2 C5 3.548(3) no . .
O2 C22 3.2338(17) no . .
N1 N2 3.089(2) no . .
N1 C9 3.3288(18) no . .
N1 C13 3.3801(14) no . .
N1 C14 3.3513(16) no . .
N2 N3 2.8729(15) no . .
N2 C2 3.117(3) no . .
N2 C3 3.020(2) no . .
N2 C4 3.164(2) no . .
N2 C13 3.582(2) no . .
N2 C22 3.523(3) no . .
N2 C23 3.413(3) no . .
N3 C12 3.156(3) no . .
N4 C5 2.869(3) no . .
N4 C22 3.2870(14) no . .
C1 C5 3.5863(18) no . .
C1 C23 3.520(3) no . .
C1 C27 3.408(3) no . .
C2 C5 3.5198(19) no . .
C2 C7 3.158(2) no . .
C2 C9 3.279(2) no . .
C3 C7 3.348(3) no . .
C3 C15 3.0484(17) no . .
C3 C23 3.0620(19) no . .
C4 C15 3.0729(17) no . .
C7 C8 2.9335(16) no . .
C7 C9 3.1387(17) no . .
C8 C11 2.7722(19) no . .
C8 C22 3.275(2) no . .
C8 C27 3.485(3) no . .
C9 C12 2.811(3) no . .
C10 C13 2.747(3) no . .
C14 C16 2.668(3) no . .
C14 C20 3.555(3) no . .
C15 C17 3.553(3) no . .
C15 C21 2.666(3) no . .
C15 C22 3.143(2) no . .
C15 C23 3.499(3) no . .
C16 C19 2.786(3) no . .
C17 C20 2.788(3) no . .
C18 C21 2.790(3) no . .
C22 C25 2.759(3) no . .
C23 C26 2.747(3) no . .
C24 C27 2.746(4) no . .
F1 O1 2.889(3) no . 2_556
F1 O2 3.247(3) no . 2_556
F1 N4 3.095(3) no . 2_556
O1 F1 2.889(3) no . 2_556
O1 N2 3.3946(15) no . 2_666
O1 C4 3.516(3) no . 2_666
O1 C17 3.5029(19) no . 2_666
O2 F1 3.247(3) no . 2_556
O2 O2 3.439(3) no . 2_656
O2 C2 3.525(3) no . 2_656
O2 C9 3.500(2) no . 2_656
O2 C27 3.545(3) no . 2_656
N1 C12 3.405(2) no . 2_655
N2 O1 3.3946(15) no . 2_666
N3 C19 3.541(3) no . 2_555
N3 C20 3.430(2) no . 2_555
N4 F1 3.095(3) no . 2_556
C2 O2 3.525(3) no . 2_656
C4 O1 3.516(3) no . 2_666
C9 O2 3.500(2) no . 2_656
C10 C18 3.466(3) no . 1_545
C12 N1 3.405(2) no . 2_655
C12 C14 3.4509(19) no . 2_655
C13 C13 3.5454(19) no . 2_655
C13 C14 3.5745(19) no . 2_655
C14 C12 3.4509(19) no . 2_655
C14 C13 3.5745(19) no . 2_655
C14 C19 3.507(2) no . 2_555
C17 O1 3.5029(19) no . 2_666
C18 C10 3.466(3) no . 1_565
C19 N3 3.541(3) no . 2_555
C19 C14 3.507(2) no . 2_555
C20 N3 3.430(2) no . 2_555
C20 C21 3.581(3) no . 2_555
C21 C20 3.581(3) no . 2_555
C21 C21 3.5576(17) no . 2_555
C27 O2 3.545(3) no . 2_656
F1 H24 2.5178 no . .
F1 H26 2.5193 no . .
O1 H3 2.5423 no . .
O1 H4 3.2512 no . .
O1 H5A 3.1525 no . .
O1 H5B 2.6480 no . .
O2 H2 2.4007 no . .
O2 H3 2.9877 no . .
O2 H5B 2.8542 no . .
N1 H2 2.6072 no . .
N1 H3 2.9684 no . .
N1 H5A 3.1159 no . .
N1 H5B 2.9585 no . .
N1 H6A 2.6390 no . .
N1 H6B 3.1749 no . .
N1 H9 3.3619 no . .
N2 H3 2.4892 no . .
N2 H4 2.8732 no . .
N2 H17 2.5767 no . .
N2 H23 2.9208 no . .
N3 H12 2.9911 no . .
N3 H20 2.5707 no . .
N4 H2 2.5672 no . .
N4 H4 3.0966 no . .
N4 H5A 3.3234 no . .
N4 H5B 2.4039 no . .
N4 H23 3.4671 no . .
C1 H3 2.7427 no . .
C1 H4 2.8925 no . .
C1 H7A 2.9281 no . .
C1 H7B 2.6387 no . .
C1 H9 2.8543 no . .
C1 H23 3.5661 no . .
C1 H27 3.3822 no . .
C2 H4 3.1527 no . .
C2 H5B 3.4760 no . .
C2 H7B 2.8898 no . .
C2 H9 3.1317 no . .
C2 H23 2.7219 no . .
C2 H27 2.6123 no . .
C3 H5A 3.2341 no . .
C3 H5B 2.6652 no . .
C3 H7B 3.3205 no . .
C3 H23 2.7751 no . .
C4 H2 2.7588 no . .
C4 H6A 2.8047 no . .
C4 H6B 3.2405 no . .
C4 H7A 3.2067 no . .
C4 H7B 2.7618 no . .
C5 H2 3.4182 no . .
C5 H3 3.3603 no . .
C5 H7A 3.2100 no . .
C5 H7B 2.6648 no . .
C6 H4 2.9529 no . .
C7 H2 2.8897 no . .
C7 H4 3.1014 no . .
C7 H5A 3.1820 no . .
C7 H5B 2.7424 no . .
C7 H9 2.9140 no . .
C8 H2 2.7744 no . .
C8 H7A 2.9059 no . .
C8 H7B 2.8996 no . .
C8 H10 3.2269 no . .
C8 H12 3.2760 no . .
C8 H27 3.1936 no . .
C9 H2 2.9978 no . .
C9 H7A 2.9839 no . .
C9 H7B 2.7772 no . .
C9 H11 3.2495 no . .
C9 H27 2.9928 no . .
C10 H12 3.2454 no . .
C11 H9 3.2562 no . .
C12 H10 3.2348 no . .
C13 H9 3.2556 no . .
C13 H11 3.2170 no . .
C14 H12 2.8177 no . .
C15 H2 3.3986 no . .
C15 H3 2.9043 no . .
C15 H4 3.1113 no . .
C15 H23 3.3321 no . .
C16 H18 3.2449 no . .
C16 H20 3.2780 no . .
C17 H19 3.2371 no . .
C18 H20 3.2347 no . .
C19 H17 3.2428 no . .
C20 H18 3.2288 no . .
C21 H17 3.2781 no . .
C21 H19 3.2468 no . .
C22 H3 2.7037 no . .
C22 H24 3.2564 no . .
C22 H26 3.2506 no . .
C23 H2 3.2578 no . .
C23 H3 2.7117 no . .
C23 H27 3.2110 no . .
C24 H26 3.2139 no . .
C25 H23 3.1952 no . .
C25 H27 3.1951 no . .
C26 H24 3.2151 no . .
C27 H2 2.5363 no . .
C27 H9 3.5123 no . .
C27 H23 3.2115 no . .
H2 H3 2.8104 no . .
H2 H5B 3.1849 no . .
H2 H7B 2.3458 no . .
H2 H9 2.5874 no . .
H2 H23 3.5478 no . .
H2 H27 2.3501 no . .
H3 H4 2.2080 no . .
H3 H5B 3.4821 no . .
H3 H23 2.1617 no . .
H4 H5A 2.2176 no . .
H4 H5B 2.7823 no . .
H4 H6A 3.0546 no . .
H5A H6A 2.2778 no . .
H5A H6B 2.5429 no . .
H5A H7B 3.5977 no . .
H5B H6A 2.8336 no . .
H5B H6B 2.2740 no . .
H5B H7B 2.7123 no . .
H6A H7A 2.3104 no . .
H6A H7B 2.8476 no . .
H6B H7A 2.4936 no . .
H6B H7B 2.3104 no . .
H7A H9 2.9219 no . .
H7B H9 2.2961 no . .
H9 H10 2.3180 no . .
H9 H27 2.7695 no . .
H10 H11 2.3040 no . .
H11 H12 2.3107 no . .
H17 H18 2.2957 no . .
H18 H19 2.3190 no . .
H19 H20 2.2818 no . .
H23 H24 2.3167 no . .
H26 H27 2.3061 no . .
F1 H4 2.8222 no . 1_445
F1 H5A 3.4033 no . 1_445
F1 H9 3.5273 no . 1_455
F1 H11 3.1524 no . 2_545
O1 H3 3.0144 no . 2_666
O1 H4 2.6898 no . 2_666
O1 H17 2.7880 no . 2_666
O1 H27 3.5943 no . 2_656
O2 H2 2.5725 no . 2_656
O2 H7B 3.0785 no . 2_656
O2 H9 2.6223 no . 2_656
O2 H24 3.3417 no . 2_556
O2 H27 2.8186 no . 2_656
N1 H12 2.6970 no . 2_655
N3 H7A 2.7014 no . 2_655
N4 H9 3.4743 no . 2_656
N4 H27 3.3963 no . 2_656
C1 H12 3.5378 no . 2_655
C5 H6B 3.4262 no . 2_766
C6 H5A 3.1821 no . 2_766
C6 H12 3.5380 no . 2_655
C6 H24 3.4046 no . 1_655
C6 H26 3.2937 no . 1_665
C7 H12 3.1323 no . 2_655
C7 H24 3.0301 no . 1_655
C10 H10 3.1068 no . 2_645
C10 H11 3.4286 no . 2_645
C10 H18 3.5162 no . 1_545
C11 H10 3.1086 no . 2_645
C12 H7A 3.5655 no . 2_655
C12 H18 3.4780 no . 2_555
C12 H19 3.5594 no . 2_555
C13 H19 3.3299 no . 2_555
C14 H7A 3.5890 no . 2_655
C14 H19 3.4901 no . 2_555
C15 H12 3.5146 no . 2_655
C17 H6A 3.4422 no . 1_455
C17 H10 3.3946 no . 1_565
C17 H27 3.5859 no . 1_565
C18 H10 3.3946 no . 1_565
C18 H12 3.4249 no . 2_555
C18 H26 3.4449 no . 1_565
C18 H27 3.5966 no . 1_565
C19 H11 3.4838 no . 1_565
C21 H7A 3.5765 no . 2_655
C23 H6B 3.5162 no . 1_455
C23 H20 3.0804 no . 2_555
C24 H6B 3.4909 no . 1_455
C24 H7B 3.3482 no . 1_455
C24 H20 2.9103 no . 2_555
C25 H19 3.5131 no . 2_555
C25 H20 3.3461 no . 2_555
C26 H5B 3.4354 no . 2_656
C26 H6A 3.3217 no . 1_445
C26 H18 3.1763 no . 1_545
C26 H19 3.2620 no . 2_555
C27 H5B 3.2730 no . 2_656
C27 H18 3.3115 no . 1_545
C27 H19 3.3553 no . 2_555
H2 O2 2.5725 no . 2_656
H2 H2 3.5965 no . 2_656
H3 O1 3.0144 no . 2_666
H4 F1 2.8222 no . 1_665
H4 O1 2.6898 no . 2_666
H4 H12 3.5200 no . 2_655
H5A F1 3.4033 no . 1_665
H5A C6 3.1821 no . 2_766
H5A H5A 3.3478 no . 2_766
H5A H6A 3.1349 no . 2_766
H5A H6B 2.5879 no . 2_766
H5A H26 3.1453 no . 1_665
H5B C26 3.4354 no . 2_656
H5B C27 3.2730 no . 2_656
H5B H6A 3.4955 no . 2_766
H5B H17 3.3287 no . 2_666
H5B H26 3.2313 no . 2_656
H5B H27 2.9112 no . 2_656
H6A C17 3.4422 no . 1_655
H6A C26 3.3217 no . 1_665
H6A H5A 3.1349 no . 2_766
H6A H5B 3.4955 no . 2_766
H6A H12 3.0341 no . 2_655
H6A H17 3.0149 no . 1_655
H6A H26 2.4229 no . 1_665
H6B C5 3.4262 no . 2_766
H6B C23 3.5162 no . 1_655
H6B C24 3.4909 no . 1_655
H6B H5A 2.5879 no . 2_766
H6B H23 2.8901 no . 1_655
H6B H24 2.8555 no . 1_655
H6B H26 3.5855 no . 2_656
H7A N3 2.7014 no . 2_655
H7A C12 3.5655 no . 2_655
H7A C14 3.5890 no . 2_655
H7A C21 3.5765 no . 2_655
H7A H12 2.7931 no . 2_655
H7A H20 3.0018 no . 2_655
H7A H24 3.0195 no . 1_655
H7B O2 3.0785 no . 2_656
H7B C24 3.3482 no . 1_655
H7B H24 2.4588 no . 1_655
H9 F1 3.5273 no . 1_655
H9 O2 2.6223 no . 2_656
H9 N4 3.4743 no . 2_656
H9 H24 3.3054 no . 1_655
H10 C10 3.1068 no . 2_645
H10 C11 3.1086 no . 2_645
H10 C17 3.3946 no . 1_545
H10 C18 3.3946 no . 1_545
H10 H10 2.5259 no . 2_645
H10 H11 2.5248 no . 2_645
H11 F1 3.1524 no . 2_545
H11 C10 3.4286 no . 2_645
H11 C19 3.4838 no . 1_545
H11 H10 2.5248 no . 2_645
H11 H19 3.4072 no . 1_545
H12 N1 2.6970 no . 2_655
H12 C1 3.5378 no . 2_655
H12 C6 3.5380 no . 2_655
H12 C7 3.1323 no . 2_655
H12 C15 3.5146 no . 2_655
H12 C18 3.4249 no . 2_555
H12 H4 3.5200 no . 2_655
H12 H6A 3.0341 no . 2_655
H12 H7A 2.7931 no . 2_655
H12 H18 3.1883 no . 2_555
H12 H26 3.4417 no . 2_545
H17 O1 2.7880 no . 2_666
H17 H5B 3.3287 no . 2_666
H17 H6A 3.0149 no . 1_455
H17 H26 3.1349 no . 1_565
H17 H27 2.9969 no . 1_565
H18 C10 3.5162 no . 1_565
H18 C12 3.4780 no . 2_555
H18 C26 3.1763 no . 1_565
H18 C27 3.3115 no . 1_565
H18 H12 3.1883 no . 2_555
H18 H18 3.5661 no . 2_565
H18 H19 2.8039 no . 2_565
H18 H26 2.7661 no . 1_565
H18 H27 3.0159 no . 1_565
H19 C12 3.5594 no . 2_555
H19 C13 3.3299 no . 2_555
H19 C14 3.4901 no . 2_555
H19 C25 3.5131 no . 2_555
H19 C26 3.2620 no . 2_555
H19 C27 3.3553 no . 2_555
H19 H11 3.4072 no . 1_565
H19 H18 2.8039 no . 2_565
H19 H26 3.5297 no . 2_555
H20 C23 3.0804 no . 2_555
H20 C24 2.9103 no . 2_555
H20 C25 3.3461 no . 2_555
H20 H7A 3.0018 no . 2_655
H20 H23 3.3027 no . 2_555
H20 H24 3.0544 no . 2_555
H23 H6B 2.8901 no . 1_455
H23 H20 3.3027 no . 2_555
H24 O2 3.3417 no . 2_556
H24 C6 3.4046 no . 1_455
H24 C7 3.0301 no . 1_455
H24 H6B 2.8555 no . 1_455
H24 H7A 3.0195 no . 1_455
H24 H7B 2.4588 no . 1_455
H24 H9 3.3054 no . 1_455
H24 H20 3.0544 no . 2_555
H26 C6 3.2937 no . 1_445
H26 C18 3.4449 no . 1_545
H26 H5A 3.1453 no . 1_445
H26 H5B 3.2313 no . 2_656
H26 H6A 2.4229 no . 1_445
H26 H6B 3.5855 no . 2_656
H26 H12 3.4417 no . 2_545
H26 H17 3.1349 no . 1_545
H26 H18 2.7661 no . 1_545
H26 H19 3.5297 no . 2_555
H27 O1 3.5943 no . 2_656
H27 O2 2.8186 no . 2_656
H27 N4 3.3963 no . 2_656
H27 C17 3.5859 no . 1_545
H27 C18 3.5966 no . 1_545
H27 H5B 2.9112 no . 2_656
H27 H17 2.9969 no . 1_545
H27 H18 3.0159 no . 1_545

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
2'-(4-fluorophenyl)-1'-nitro-1',2',5',6',7',7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine]
_chemical_name_common            RT-L4F
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol, Chloroform'
