# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_is_rfmyca32
_database_code_depnum_ccdc_archive 'CCDC 2164808'
loop_
_audit_author_name
_audit_author_address
'Villinger A.'
;University of Rostock
Germany
;
_audit_update_record             
;
2022-04-06 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

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

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 N2 O'
_chemical_formula_sum            'C20 H16 N2 O'
_chemical_formula_weight         300.35

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'
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'

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

# CRYSTAL DATA

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6764(15)
_cell_length_b                   10.420(2)
_cell_length_c                   10.633(2)
_cell_angle_alpha                96.896(6)
_cell_angle_beta                 102.772(5)
_cell_angle_gamma                106.607(5)
_cell_volume                     779.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9927
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      35.08

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             316
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7204
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'

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

# EXPERIMENTAL DATA


_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34631
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.955
_diffrn_reflns_theta_max         32.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5636
_reflns_number_gt                4989
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

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

# REFINEMENT DATA 

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0718P)²+0.1675P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5636
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1235
_refine_ls_wR_factor_gt          0.1176
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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

# ATOMIC COORDINATES AND DISPLACEMENT 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.44311(11) 0.79009(7) 0.01771(7) 0.03050(15) Uani 1 1 d . . . . .
N1 N 0.48149(8) 0.57712(6) 0.17357(6) 0.01524(12) Uani 1 1 d . . . . .
N2 N 0.77040(9) 0.62322(7) 0.14345(7) 0.02195(14) Uani 1 1 d . . . . .
C1 C 0.58256(13) 0.75487(9) 0.04080(9) 0.02648(17) Uani 1 1 d . . . . .
H1 H 0.6826 0.7978 0.0055 0.032 Uiso 1 1 calc R U . . .
C2 C 0.60963(11) 0.65268(8) 0.11776(7) 0.01851(14) Uani 1 1 d . . . . .
C3 C 0.74356(11) 0.52598(9) 0.21802(8) 0.02113(15) Uani 1 1 d . . . . .
H3 H 0.8342 0.4842 0.2516 0.025 Uiso 1 1 calc R U . . .
C4 C 0.56626(10) 0.49655(8) 0.23803(7) 0.01885(14) Uani 1 1 d . . . . .
H4 H 0.5136 0.4326 0.2871 0.023 Uiso 1 1 calc R U . . .
C5 C 0.28826(10) 0.58031(8) 0.16484(7) 0.01808(13) Uani 1 1 d . . . . .
H5A H 0.2204 0.5696 0.0715 0.022 Uiso 1 1 calc R U . . .
H5B H 0.2943 0.6699 0.2124 0.022 Uiso 1 1 calc R U . . .
C6 C 0.18159(10) 0.46844(7) 0.22274(7) 0.01619(13) Uani 1 1 d . . . . .
C7 C 0.19907(10) 0.48607(7) 0.35912(7) 0.01563(13) Uani 1 1 d . . . . .
C8 C 0.09664(11) 0.38020(8) 0.40963(8) 0.02011(14) Uani 1 1 d . . . . .
H8 H 0.1074 0.3917 0.5013 0.024 Uiso 1 1 calc R U . . .
C9 C -0.02056(12) 0.25850(8) 0.32645(9) 0.02499(16) Uani 1 1 d . . . . .
H9 H -0.0899 0.1871 0.3614 0.030 Uiso 1 1 calc R U . . .
C10 C -0.03697(12) 0.24060(9) 0.19221(9) 0.02612(17) Uani 1 1 d . . . . .
H10 H -0.1168 0.1570 0.1356 0.031 Uiso 1 1 calc R U . . .
C11 C 0.06368(11) 0.34530(8) 0.14111(8) 0.02146(15) Uani 1 1 d . . . . .
H11 H 0.0520 0.3328 0.0493 0.026 Uiso 1 1 calc R U . . .
C12 C 0.32109(10) 0.61062(8) 0.44566(7) 0.01719(13) Uani 1 1 d . . . . .
C13 C 0.42644(10) 0.71499(7) 0.51840(7) 0.01761(13) Uani 1 1 d . . . . .
C14 C 0.55573(10) 0.83798(7) 0.60390(7) 0.01767(13) Uani 1 1 d . . . . .
C15 C 0.68905(11) 0.92777(8) 0.55624(8) 0.02070(14) Uani 1 1 d . . . . .
C16 C 0.81282(12) 1.04655(8) 0.64261(10) 0.02734(18) Uani 1 1 d . . . . .
H16 H 0.9029 1.1090 0.6119 0.033 Uiso 1 1 calc R U . . .
C17 C 0.80745(13) 1.07564(9) 0.77234(10) 0.02986(19) Uani 1 1 d . . . . .
H17 H 0.8944 1.1567 0.8294 0.036 Uiso 1 1 calc R U . . .
C18 C 0.67530(14) 0.98654(9) 0.81875(9) 0.02755(17) Uani 1 1 d . . . . .
H18 H 0.6711 1.0065 0.9074 0.033 Uiso 1 1 calc R U . . .
C19 C 0.54922(12) 0.86804(8) 0.73469(8) 0.02179(15) Uani 1 1 d . . . . .
H19 H 0.4581 0.8070 0.7659 0.026 Uiso 1 1 calc R U . . .
C20 C 0.69529(13) 0.89490(9) 0.41621(9) 0.02746(17) Uani 1 1 d . . . . .
H20A H 0.5777 0.8948 0.3569 0.041 Uiso 1 1 calc R U . . .
H20B H 0.7101 0.8046 0.3988 0.041 Uiso 1 1 calc R U . . .
H20C H 0.8022 0.9638 0.4015 0.041 Uiso 1 1 calc R U . . .


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

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2128(12) . ?
N1 C4 1.3606(9) . ?
N1 C2 1.3664(9) . ?
N1 C5 1.4758(10) . ?
N2 C2 1.3341(10) . ?
N2 C3 1.3578(11) . ?
C1 C2 1.4516(11) . ?
C1 H1 0.9500 . ?
C3 C4 1.3772(11) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C5 C6 1.5026(10) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C11 1.3930(10) . ?
C6 C7 1.4109(10) . ?
C7 C8 1.3988(10) . ?
C7 C12 1.4303(10) . ?
C8 C9 1.3880(11) . ?
C8 H8 0.9500 . ?
C9 C10 1.3896(13) . ?
C9 H9 0.9500 . ?
C10 C11 1.3887(12) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.2056(10) . ?
C13 C14 1.4312(10) . ?
C14 C19 1.4035(11) . ?
C14 C15 1.4054(11) . ?
C15 C16 1.3954(11) . ?
C15 C20 1.5017(12) . ?
C16 C17 1.3886(15) . ?
C16 H16 0.9500 . ?
C17 C18 1.3884(14) . ?
C17 H17 0.9500 . ?
C18 C19 1.3892(11) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C2 106.44(6) . . ?
C4 N1 C5 126.44(6) . . ?
C2 N1 C5 127.11(6) . . ?
C2 N2 C3 105.08(6) . . ?
O1 C1 C2 125.57(8) . . ?
O1 C1 H1 117.2 . . ?
C2 C1 H1 117.2 . . ?
N2 C2 N1 111.69(7) . . ?
N2 C2 C1 122.13(7) . . ?
N1 C2 C1 126.17(7) . . ?
N2 C3 C4 110.37(7) . . ?
N2 C3 H3 124.8 . . ?
C4 C3 H3 124.8 . . ?
N1 C4 C3 106.42(7) . . ?
N1 C4 H4 126.8 . . ?
C3 C4 H4 126.8 . . ?
N1 C5 C6 111.20(6) . . ?
N1 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
N1 C5 H5B 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C11 C6 C7 119.26(7) . . ?
C11 C6 C5 119.79(7) . . ?
C7 C6 C5 120.95(6) . . ?
C8 C7 C6 119.46(7) . . ?
C8 C7 C12 119.99(6) . . ?
C6 C7 C12 120.55(6) . . ?
C9 C8 C7 120.32(7) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.30(7) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 119.79(7) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C6 120.87(7) . . ?
C10 C11 H11 119.6 . . ?
C6 C11 H11 119.6 . . ?
C13 C12 C7 178.94(8) . . ?
C12 C13 C14 178.44(8) . . ?
C19 C14 C15 120.41(7) . . ?
C19 C14 C13 119.93(7) . . ?
C15 C14 C13 119.65(7) . . ?
C16 C15 C14 117.97(8) . . ?
C16 C15 C20 121.91(8) . . ?
C14 C15 C20 120.12(7) . . ?
C17 C16 C15 121.60(8) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C18 C17 C16 120.13(8) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 119.54(8) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C14 120.35(8) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 C2 N1 -0.05(9) . . . . ?
C3 N2 C2 C1 179.18(7) . . . . ?
C4 N1 C2 N2 0.26(8) . . . . ?
C5 N1 C2 N2 -179.05(6) . . . . ?
C4 N1 C2 C1 -178.93(8) . . . . ?
C5 N1 C2 C1 1.76(12) . . . . ?
O1 C1 C2 N2 -177.23(8) . . . . ?
O1 C1 C2 N1 1.89(14) . . . . ?
C2 N2 C3 C4 -0.18(9) . . . . ?
C2 N1 C4 C3 -0.36(8) . . . . ?
C5 N1 C4 C3 178.96(7) . . . . ?
N2 C3 C4 N1 0.34(9) . . . . ?
C4 N1 C5 C6 -7.36(10) . . . . ?
C2 N1 C5 C6 171.82(7) . . . . ?
N1 C5 C6 C11 -95.58(8) . . . . ?
N1 C5 C6 C7 84.36(8) . . . . ?
C11 C6 C7 C8 -0.54(11) . . . . ?
C5 C6 C7 C8 179.52(7) . . . . ?
C11 C6 C7 C12 179.11(7) . . . . ?
C5 C6 C7 C12 -0.83(10) . . . . ?
C6 C7 C8 C9 0.32(11) . . . . ?
C12 C7 C8 C9 -179.33(7) . . . . ?
C7 C8 C9 C10 0.12(13) . . . . ?
C8 C9 C10 C11 -0.34(13) . . . . ?
C9 C10 C11 C6 0.12(13) . . . . ?
C7 C6 C11 C10 0.33(11) . . . . ?
C5 C6 C11 C10 -179.73(7) . . . . ?
C19 C14 C15 C16 -0.15(11) . . . . ?
C13 C14 C15 C16 -179.93(7) . . . . ?
C19 C14 C15 C20 179.96(8) . . . . ?
C13 C14 C15 C20 0.18(11) . . . . ?
C14 C15 C16 C17 0.75(12) . . . . ?
C20 C15 C16 C17 -179.36(8) . . . . ?
C15 C16 C17 C18 -0.81(14) . . . . ?
C16 C17 C18 C19 0.25(13) . . . . ?
C17 C18 C19 C14 0.34(13) . . . . ?
C15 C14 C19 C18 -0.39(12) . . . . ?
C13 C14 C19 C18 179.39(7) . . . . ?

_refine_diff_density_max         0.478
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_is_rfmyda501
_database_code_depnum_ccdc_archive 'CCDC 2164812'
loop_
_audit_author_name
_audit_author_address
'Villinger A.'
;University of Rostock
Germany
;
_audit_update_record             
;
2022-04-06 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

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

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H16 F2 N2 O2'
_chemical_formula_sum            'C24 H16 F2 N2 O2'
_chemical_formula_weight         402.39

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'

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

# CRYSTAL DATA

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6890(13)
_cell_length_b                   11.222(2)
_cell_length_c                   13.775(3)
_cell_angle_alpha                109.827(7)
_cell_angle_beta                 97.404(7)
_cell_angle_gamma                104.970(7)
_cell_volume                     912.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9879
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      34.13

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.990
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   0.901
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.452788
_exptl_absorpt_correction_T_max  0.746926
_exptl_absorpt_process_details   '(TWINABS; Sheldrick, 2004)'

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

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Apex Kappa-II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4376
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_av_R_equivalents  0.0913
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         3.237
_diffrn_reflns_theta_max         27.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4376
_reflns_number_gt                3432
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

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

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine. 

 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1478P)²+0.0021P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4376
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.2042
_refine_ls_wR_factor_gt          0.1897
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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

# ATOMIC COORDINATES AND DISPLACEMENT 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_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 0.11406(17) 0.69527(11) 0.00068(9) 0.0259(3) Uani 1 1 d . . . . .
F2 F 0.49596(19) 0.78308(12) -0.03226(9) 0.0306(3) Uani 1 1 d . . . . .
O1 O 0.9501(2) 0.34188(15) 0.42148(12) 0.0310(4) Uani 1 1 d . . . . .
O2 O 0.3904(2) 0.08347(14) 0.67831(11) 0.0273(3) Uani 1 1 d . . . . .
N1 N 0.7629(2) 0.58632(14) 0.20106(12) 0.0208(3) Uani 1 1 d . . . . .
N2 N 0.4340(2) 0.50496(14) 0.22402(12) 0.0178(3) Uani 1 1 d . . . . .
C1 C 0.6465(3) 0.51708(17) 0.24762(14) 0.0190(4) Uani 1 1 d . . . . .
C2 C 0.7301(3) 0.46322(18) 0.31957(14) 0.0204(4) Uani 1 1 d . . . . .
H2 H 0.8699 0.5129 0.3630 0.024 Uiso 1 1 calc R U . . .
C3 C 0.6306(3) 0.35031(17) 0.33132(14) 0.0198(4) Uani 1 1 d . . . . .
C4 C 0.4201(3) 0.25232(17) 0.26475(13) 0.0189(4) Uani 1 1 d . . . . .
C5 C 0.3945(3) 0.11508(18) 0.23060(15) 0.0244(4) Uani 1 1 d . . . . .
H5 H 0.5086 0.0872 0.2527 0.029 Uiso 1 1 calc R U . . .
C6 C 0.2040(3) 0.01980(19) 0.16488(15) 0.0284(4) Uani 1 1 d . . . . .
H6 H 0.1895 -0.0726 0.1412 0.034 Uiso 1 1 calc R U . . .
C7 C 0.0354(3) 0.0591(2) 0.13379(15) 0.0290(5) Uani 1 1 d . . . . .
H7 H -0.0953 -0.0063 0.0895 0.035 Uiso 1 1 calc R U . . .
C8 C 0.0575(3) 0.19459(18) 0.16746(14) 0.0232(4) Uani 1 1 d . . . . .
H8 H -0.0589 0.2214 0.1463 0.028 Uiso 1 1 calc R U . . .
C9 C 0.2495(3) 0.29151(16) 0.23211(13) 0.0185(4) Uani 1 1 d . . . . .
C10 C 0.2722(3) 0.43849(17) 0.26736(14) 0.0190(4) Uani 1 1 d . . . . .
H10A H 0.1339 0.4482 0.2427 0.023 Uiso 1 1 calc R U . . .
H10B H 0.3130 0.4813 0.3459 0.023 Uiso 1 1 calc R U . . .
C11 C 0.4115(3) 0.57175(16) 0.15761(14) 0.0174(4) Uani 1 1 d . . . . .
C12 C 0.2350(3) 0.59627(16) 0.11248(14) 0.0190(4) Uani 1 1 d . . . . .
H12 H 0.0977 0.5660 0.1245 0.023 Uiso 1 1 calc R U . . .
C13 C 0.2753(3) 0.66729(17) 0.04960(14) 0.0201(4) Uani 1 1 d . . . . .
C14 C 0.4778(3) 0.71390(17) 0.03191(14) 0.0209(4) Uani 1 1 d . . . . .
C15 C 0.6505(3) 0.69172(17) 0.07699(15) 0.0219(4) Uani 1 1 d . . . . .
H15 H 0.7871 0.7235 0.0647 0.026 Uiso 1 1 calc R U . . .
C16 C 0.6171(3) 0.61950(16) 0.14258(14) 0.0185(4) Uani 1 1 d . . . . .
C17 C 0.7585(3) 0.31819(18) 0.41307(14) 0.0215(4) Uani 1 1 d . . . . .
C18 C 0.6511(3) 0.26172(17) 0.48307(14) 0.0192(4) Uani 1 1 d . . . . .
C19 C 0.7698(3) 0.22038(19) 0.54908(15) 0.0244(4) Uani 1 1 d . . . . .
H19 H 0.9153 0.2316 0.5485 0.029 Uiso 1 1 calc R U . . .
C20 C 0.6821(3) 0.1640(2) 0.61466(15) 0.0261(4) Uani 1 1 d . . . . .
H20 H 0.7666 0.1372 0.6588 0.031 Uiso 1 1 calc R U . . .
C21 C 0.4682(3) 0.14649(18) 0.61593(14) 0.0213(4) Uani 1 1 d . . . . .
C22 C 0.3505(3) 0.19349(18) 0.55548(14) 0.0221(4) Uani 1 1 d . . . . .
H22 H 0.2074 0.1867 0.5593 0.027 Uiso 1 1 calc R U . . .
C23 C 0.4405(3) 0.25026(18) 0.48956(14) 0.0212(4) Uani 1 1 d . . . . .
H23 H 0.3582 0.2816 0.4485 0.025 Uiso 1 1 calc R U . . .
C24 C 0.1668(3) 0.0489(2) 0.67165(17) 0.0312(5) Uani 1 1 d . . . . .
H24A H 0.0888 -0.0001 0.5971 0.047 Uiso 1 1 calc R U . . .
H24B H 0.1297 0.1307 0.7017 0.047 Uiso 1 1 calc R U . . .
H24C H 0.1282 -0.0075 0.7117 0.047 Uiso 1 1 calc R U . . .


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

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C13 1.359(2) . ?
F2 C14 1.358(2) . ?
O1 C17 1.221(2) . ?
O2 C21 1.359(2) . ?
O2 C24 1.428(3) . ?
N1 C1 1.333(2) . ?
N1 C16 1.388(2) . ?
N2 C1 1.377(2) . ?
N2 C11 1.382(2) . ?
N2 C10 1.462(2) . ?
C1 C2 1.449(2) . ?
C2 C3 1.344(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.489(2) . ?
C3 C17 1.522(2) . ?
C4 C9 1.400(2) . ?
C4 C5 1.405(3) . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.397(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.513(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.397(2) . ?
C11 C16 1.410(2) . ?
C12 C13 1.369(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.405(3) . ?
C14 C15 1.360(3) . ?
C15 C16 1.407(3) . ?
C15 H15 0.9500 . ?
C17 C18 1.485(3) . ?
C18 C23 1.398(3) . ?
C18 C19 1.401(2) . ?
C19 C20 1.376(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.396(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.391(2) . ?
C22 C23 1.389(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 O2 C24 117.61(15) . . ?
C1 N1 C16 104.42(14) . . ?
C1 N2 C11 106.68(14) . . ?
C1 N2 C10 124.63(15) . . ?
C11 N2 C10 128.63(14) . . ?
N1 C1 N2 113.11(16) . . ?
N1 C1 C2 124.96(16) . . ?
N2 C1 C2 121.88(16) . . ?
C3 C2 C1 126.78(16) . . ?
C3 C2 H2 116.6 . . ?
C1 C2 H2 116.6 . . ?
C2 C3 C4 125.06(16) . . ?
C2 C3 C17 115.19(15) . . ?
C4 C3 C17 119.50(15) . . ?
C9 C4 C5 118.84(16) . . ?
C9 C4 C3 122.65(15) . . ?
C5 C4 C3 118.48(16) . . ?
C6 C5 C4 120.70(17) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C7 C6 C5 120.18(18) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 119.91(17) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C9 120.46(18) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C4 119.90(16) . . ?
C8 C9 C10 119.97(15) . . ?
C4 C9 C10 120.12(14) . . ?
N2 C10 C9 110.35(14) . . ?
N2 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
N2 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
N2 C11 C12 131.72(15) . . ?
N2 C11 C16 105.33(15) . . ?
C12 C11 C16 122.93(16) . . ?
C13 C12 C11 114.81(16) . . ?
C13 C12 H12 122.6 . . ?
C11 C12 H12 122.6 . . ?
F1 C13 C12 119.67(16) . . ?
F1 C13 C14 117.02(16) . . ?
C12 C13 C14 123.31(17) . . ?
F2 C14 C15 120.65(16) . . ?
F2 C14 C13 117.38(16) . . ?
C15 C14 C13 121.96(17) . . ?
C14 C15 C16 116.80(16) . . ?
C14 C15 H15 121.6 . . ?
C16 C15 H15 121.6 . . ?
N1 C16 C15 129.42(16) . . ?
N1 C16 C11 110.41(15) . . ?
C15 C16 C11 120.15(16) . . ?
O1 C17 C18 120.82(16) . . ?
O1 C17 C3 119.14(17) . . ?
C18 C17 C3 120.02(15) . . ?
C23 C18 C19 117.69(17) . . ?
C23 C18 C17 124.30(16) . . ?
C19 C18 C17 118.00(16) . . ?
C20 C19 C18 122.02(17) . . ?
C20 C19 H19 119.0 . . ?
C18 C19 H19 119.0 . . ?
C19 C20 C21 119.57(17) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
O2 C21 C22 124.60(16) . . ?
O2 C21 C20 116.01(16) . . ?
C22 C21 C20 119.39(17) . . ?
C23 C22 C21 120.48(16) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C18 120.68(16) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N1 C1 N2 -0.9(2) . . . . ?
C16 N1 C1 C2 -178.46(16) . . . . ?
C11 N2 C1 N1 -0.2(2) . . . . ?
C10 N2 C1 N1 -177.63(14) . . . . ?
C11 N2 C1 C2 177.43(15) . . . . ?
C10 N2 C1 C2 0.0(3) . . . . ?
N1 C1 C2 C3 -147.7(2) . . . . ?
N2 C1 C2 C3 34.9(3) . . . . ?
C1 C2 C3 C4 5.7(3) . . . . ?
C1 C2 C3 C17 179.77(16) . . . . ?
C2 C3 C4 C9 -40.6(3) . . . . ?
C17 C3 C4 C9 145.49(17) . . . . ?
C2 C3 C4 C5 137.22(19) . . . . ?
C17 C3 C4 C5 -36.7(2) . . . . ?
C9 C4 C5 C6 0.5(3) . . . . ?
C3 C4 C5 C6 -177.42(16) . . . . ?
C4 C5 C6 C7 -1.2(3) . . . . ?
C5 C6 C7 C8 0.7(3) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
C7 C8 C9 C4 -1.0(3) . . . . ?
C7 C8 C9 C10 179.44(17) . . . . ?
C5 C4 C9 C8 0.6(3) . . . . ?
C3 C4 C9 C8 178.42(16) . . . . ?
C5 C4 C9 C10 -179.90(15) . . . . ?
C3 C4 C9 C10 -2.0(3) . . . . ?
C1 N2 C10 C9 -63.2(2) . . . . ?
C11 N2 C10 C9 120.02(17) . . . . ?
C8 C9 C10 N2 -116.24(17) . . . . ?
C4 C9 C10 N2 64.2(2) . . . . ?
C1 N2 C11 C12 -177.24(18) . . . . ?
C10 N2 C11 C12 0.0(3) . . . . ?
C1 N2 C11 C16 1.24(18) . . . . ?
C10 N2 C11 C16 178.48(16) . . . . ?
N2 C11 C12 C13 -179.94(16) . . . . ?
C16 C11 C12 C13 1.8(2) . . . . ?
C11 C12 C13 F1 179.18(14) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
F1 C13 C14 F2 0.1(2) . . . . ?
C12 C13 C14 F2 179.97(15) . . . . ?
F1 C13 C14 C15 179.93(16) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
F2 C14 C15 C16 179.81(14) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C1 N1 C16 C15 -179.54(17) . . . . ?
C1 N1 C16 C11 1.67(19) . . . . ?
C14 C15 C16 N1 -177.59(17) . . . . ?
C14 C15 C16 C11 1.1(3) . . . . ?
N2 C11 C16 N1 -1.84(18) . . . . ?
C12 C11 C16 N1 176.81(15) . . . . ?
N2 C11 C16 C15 179.24(15) . . . . ?
C12 C11 C16 C15 -2.1(3) . . . . ?
C2 C3 C17 O1 -37.6(2) . . . . ?
C4 C3 C17 O1 136.85(18) . . . . ?
C2 C3 C17 C18 140.99(17) . . . . ?
C4 C3 C17 C18 -44.6(2) . . . . ?
O1 C17 C18 C23 170.11(17) . . . . ?
C3 C17 C18 C23 -8.5(3) . . . . ?
O1 C17 C18 C19 -8.1(3) . . . . ?
C3 C17 C18 C19 173.29(16) . . . . ?
C23 C18 C19 C20 3.2(3) . . . . ?
C17 C18 C19 C20 -178.44(17) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C24 O2 C21 C22 7.8(3) . . . . ?
C24 O2 C21 C20 -172.42(17) . . . . ?
C19 C20 C21 O2 176.48(16) . . . . ?
C19 C20 C21 C22 -3.8(3) . . . . ?
O2 C21 C22 C23 -176.48(16) . . . . ?
C20 C21 C22 C23 3.8(3) . . . . ?
C21 C22 C23 C18 -0.3(3) . . . . ?
C19 C18 C23 C22 -3.2(3) . . . . ?
C17 C18 C23 C22 178.59(16) . . . . ?

_refine_diff_density_max         0.469
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.104

####################################################################### 
# 
# 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_is_rfmydc501
_database_code_depnum_ccdc_archive 'CCDC 2164810'
loop_
_audit_author_name
_audit_author_address
'Villinger A.'
;University of Rostock
Germany
;
_audit_update_record             
;
2022-04-06 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

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

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H16 F2 N2 O'
_chemical_formula_sum            'C24 H16 F2 N2 O'
_chemical_formula_weight         386.39

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'

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

# CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   23.3551(19)
_cell_length_b                   6.4154(5)
_cell_length_c                   14.5468(12)
_cell_angle_alpha                90
_cell_angle_beta                 124.943(2)
_cell_angle_gamma                90
_cell_volume                     1786.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9633
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      31.69

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6752
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

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

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Apex Kappa-II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35432
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.806
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5188
_reflns_number_gt                4600
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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.
;

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

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

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine. 

 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0511P)²+0.5869P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(8)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         5188
_refine_ls_number_parameters     264
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.0998
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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

# ATOMIC COORDINATES AND DISPLACEMENT 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_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 1.02015(7) 0.4559(3) 0.87391(14) 0.0469(4) Uani 1 1 d . . . . .
F2 F 0.97865(7) 0.0820(2) 0.88590(13) 0.0396(3) Uani 1 1 d . . . . .
O1 O 0.55646(9) 0.9212(3) 0.65053(16) 0.0408(4) Uani 1 1 d . . . . .
N1 N 0.79039(9) 0.7164(3) 0.74724(15) 0.0265(4) Uani 1 1 d . . . . .
N2 N 0.75685(8) 0.3994(3) 0.76588(13) 0.0217(3) Uani 1 1 d . . . . .
C1 C 0.73914(10) 0.6042(3) 0.73669(16) 0.0233(4) Uani 1 1 d . . . . .
C2 C 0.67073(10) 0.6852(3) 0.69627(17) 0.0243(4) Uani 1 1 d . . . . .
H2 H 0.6539 0.7960 0.6436 0.029 Uiso 1 1 calc R U . . .
C3 C 0.62827(10) 0.6200(3) 0.72547(16) 0.0225(4) Uani 1 1 d . . . . .
C4 C 0.64403(9) 0.4601(3) 0.80973(15) 0.0218(4) Uani 1 1 d . . . . .
C5 C 0.61822(10) 0.4874(4) 0.87558(16) 0.0268(4) Uani 1 1 d . . . . .
H5 H 0.5924 0.6095 0.8664 0.032 Uiso 1 1 calc R U . . .
C6 C 0.62973(11) 0.3397(4) 0.95350(17) 0.0301(5) Uani 1 1 d . . . . .
H6 H 0.6113 0.3599 0.9965 0.036 Uiso 1 1 calc R U . . .
C7 C 0.66804(11) 0.1622(4) 0.96919(18) 0.0301(5) Uani 1 1 d . . . . .
H7 H 0.6756 0.0601 1.0224 0.036 Uiso 1 1 calc R U . . .
C8 C 0.69548(10) 0.1340(3) 0.90670(17) 0.0266(4) Uani 1 1 d . . . . .
H8 H 0.7227 0.0137 0.9187 0.032 Uiso 1 1 calc R U . . .
C9 C 0.68348(9) 0.2799(3) 0.82691(16) 0.0206(4) Uani 1 1 d . . . . .
C10 C 0.70895(10) 0.2374(3) 0.75429(17) 0.0230(4) Uani 1 1 d . . . . .
H10A H 0.7331 0.1009 0.7752 0.028 Uiso 1 1 calc R U . . .
H10B H 0.6684 0.2293 0.6749 0.028 Uiso 1 1 calc R U . . .
C11 C 0.82465(10) 0.3764(3) 0.79773(16) 0.0225(4) Uani 1 1 d . . . . .
C12 C 0.86760(11) 0.2022(3) 0.83014(17) 0.0262(4) Uani 1 1 d . . . . .
H12 H 0.8529 0.0668 0.8345 0.031 Uiso 1 1 calc R U . . .
C13 C 0.93300(11) 0.2411(4) 0.85529(19) 0.0292(4) Uani 1 1 d . . . . .
C14 C 0.95485(11) 0.4382(4) 0.8478(2) 0.0326(5) Uani 1 1 d . . . . .
C15 C 0.91202(12) 0.6083(4) 0.81273(19) 0.0317(4) Uani 1 1 d . . . . .
H15 H 0.9271 0.7418 0.8064 0.038 Uiso 1 1 calc R U . . .
C16 C 0.84473(11) 0.5765(3) 0.78650(17) 0.0258(4) Uani 1 1 d . . . . .
C17 C 0.55927(11) 0.7351(3) 0.66826(17) 0.0261(4) Uani 1 1 d . . . . .
C18 C 0.49523(10) 0.6130(4) 0.63109(16) 0.0259(4) Uani 1 1 d . . . . .
C19 C 0.43842(12) 0.7157(4) 0.61965(19) 0.0340(5) Uani 1 1 d . . . . .
H19 H 0.4417 0.8595 0.6378 0.041 Uiso 1 1 calc R U . . .
C20 C 0.37748(12) 0.6067(5) 0.58183(19) 0.0384(6) Uani 1 1 d . . . . .
H20 H 0.3397 0.6762 0.5763 0.046 Uiso 1 1 calc R U . . .
C21 C 0.37053(11) 0.3985(5) 0.55188(18) 0.0363(5) Uani 1 1 d . . . . .
C22 C 0.42685(11) 0.2980(4) 0.56210(19) 0.0332(5) Uani 1 1 d . . . . .
H22 H 0.4226 0.1561 0.5404 0.040 Uiso 1 1 calc R U . . .
C23 C 0.48922(10) 0.4036(4) 0.60381(17) 0.0273(4) Uani 1 1 d . . . . .
H23 H 0.5279 0.3317 0.6136 0.033 Uiso 1 1 calc R U . . .
C24 C 0.30373(13) 0.2825(6) 0.5102(2) 0.0508(8) Uani 1 1 d . . . . .
H24A H 0.2646 0.3542 0.4446 0.076 Uiso 1 1 calc R U . . .
H24B H 0.2960 0.2776 0.5696 0.076 Uiso 1 1 calc R U . . .
H24C H 0.3073 0.1402 0.4894 0.076 Uiso 1 1 calc R U . . .


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

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C14 1.349(2) . ?
F2 C13 1.354(3) . ?
O1 C17 1.215(3) . ?
N1 C1 1.328(3) . ?
N1 C16 1.383(3) . ?
N2 C1 1.370(3) . ?
N2 C11 1.380(2) . ?
N2 C10 1.464(2) . ?
C1 C2 1.447(3) . ?
C2 C3 1.350(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.474(3) . ?
C3 C17 1.516(3) . ?
C4 C5 1.405(3) . ?
C4 C9 1.409(3) . ?
C5 C6 1.381(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.505(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.392(3) . ?
C11 C16 1.408(3) . ?
C12 C13 1.375(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(3) . ?
C14 C15 1.367(3) . ?
C15 C16 1.404(3) . ?
C15 H15 0.9500 . ?
C17 C18 1.489(3) . ?
C18 C23 1.385(3) . ?
C18 C19 1.404(3) . ?
C19 C20 1.386(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.394(3) . ?
C21 C24 1.507(3) . ?
C22 C23 1.392(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C16 104.44(17) . . ?
C1 N2 C11 106.93(16) . . ?
C1 N2 C10 124.76(16) . . ?
C11 N2 C10 128.10(17) . . ?
N1 C1 N2 113.07(17) . . ?
N1 C1 C2 124.40(19) . . ?
N2 C1 C2 122.51(18) . . ?
C3 C2 C1 126.90(19) . . ?
C3 C2 H2 116.6 . . ?
C1 C2 H2 116.6 . . ?
C2 C3 C4 126.78(17) . . ?
C2 C3 C17 114.69(18) . . ?
C4 C3 C17 118.44(17) . . ?
C5 C4 C9 118.29(17) . . ?
C5 C4 C3 118.67(18) . . ?
C9 C4 C3 123.04(16) . . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 120.24(19) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C8 119.7(2) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 120.7(2) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C4 119.98(17) . . ?
C8 C9 C10 119.54(18) . . ?
C4 C9 C10 120.37(17) . . ?
N2 C10 C9 111.94(16) . . ?
N2 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
N2 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
N2 C11 C12 131.73(19) . . ?
N2 C11 C16 104.95(18) . . ?
C12 C11 C16 123.26(17) . . ?
C13 C12 C11 114.8(2) . . ?
C13 C12 H12 122.6 . . ?
C11 C12 H12 122.6 . . ?
F2 C13 C12 119.8(2) . . ?
F2 C13 C14 117.15(18) . . ?
C12 C13 C14 123.1(2) . . ?
F1 C14 C15 120.3(2) . . ?
F1 C14 C13 117.5(2) . . ?
C15 C14 C13 122.20(19) . . ?
C14 C15 C16 116.8(2) . . ?
C14 C15 H15 121.6 . . ?
C16 C15 H15 121.6 . . ?
N1 C16 C15 129.6(2) . . ?
N1 C16 C11 110.60(17) . . ?
C15 C16 C11 119.8(2) . . ?
O1 C17 C18 121.27(19) . . ?
O1 C17 C3 120.4(2) . . ?
C18 C17 C3 118.27(18) . . ?
C23 C18 C19 119.2(2) . . ?
C23 C18 C17 122.04(19) . . ?
C19 C18 C17 118.7(2) . . ?
C20 C19 C18 119.7(2) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C21 C20 C19 121.3(2) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C22 118.6(2) . . ?
C20 C21 C24 120.7(3) . . ?
C22 C21 C24 120.7(3) . . ?
C23 C22 C21 120.6(2) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C18 C23 C22 120.4(2) . . ?
C18 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N1 C1 N2 -0.5(2) . . . . ?
C16 N1 C1 C2 -179.16(18) . . . . ?
C11 N2 C1 N1 0.0(2) . . . . ?
C10 N2 C1 N1 -175.09(17) . . . . ?
C11 N2 C1 C2 178.61(18) . . . . ?
C10 N2 C1 C2 3.6(3) . . . . ?
N1 C1 C2 C3 -149.5(2) . . . . ?
N2 C1 C2 C3 32.0(3) . . . . ?
C1 C2 C3 C4 3.7(3) . . . . ?
C1 C2 C3 C17 -179.7(2) . . . . ?
C2 C3 C4 C5 144.0(2) . . . . ?
C17 C3 C4 C5 -32.4(3) . . . . ?
C2 C3 C4 C9 -36.4(3) . . . . ?
C17 C3 C4 C9 147.14(18) . . . . ?
C9 C4 C5 C6 -1.4(3) . . . . ?
C3 C4 C5 C6 178.15(18) . . . . ?
C4 C5 C6 C7 0.9(3) . . . . ?
C5 C6 C7 C8 0.5(3) . . . . ?
C6 C7 C8 C9 -1.4(3) . . . . ?
C7 C8 C9 C4 0.9(3) . . . . ?
C7 C8 C9 C10 -175.22(18) . . . . ?
C5 C4 C9 C8 0.5(3) . . . . ?
C3 C4 C9 C8 -179.04(18) . . . . ?
C5 C4 C9 C10 176.62(18) . . . . ?
C3 C4 C9 C10 -2.9(3) . . . . ?
C1 N2 C10 C9 -63.5(2) . . . . ?
C11 N2 C10 C9 122.5(2) . . . . ?
C8 C9 C10 N2 -121.60(19) . . . . ?
C4 C9 C10 N2 62.3(2) . . . . ?
C1 N2 C11 C12 -176.7(2) . . . . ?
C10 N2 C11 C12 -1.8(3) . . . . ?
C1 N2 C11 C16 0.6(2) . . . . ?
C10 N2 C11 C16 175.42(18) . . . . ?
N2 C11 C12 C13 179.4(2) . . . . ?
C16 C11 C12 C13 2.6(3) . . . . ?
C11 C12 C13 F2 -178.85(18) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
F2 C13 C14 F1 -1.4(3) . . . . ?
C12 C13 C14 F1 -179.5(2) . . . . ?
F2 C13 C14 C15 176.9(2) . . . . ?
C12 C13 C14 C15 -1.2(4) . . . . ?
F1 C14 C15 C16 179.58(19) . . . . ?
C13 C14 C15 C16 1.4(3) . . . . ?
C1 N1 C16 C15 179.9(2) . . . . ?
C1 N1 C16 C11 0.9(2) . . . . ?
C14 C15 C16 N1 -178.5(2) . . . . ?
C14 C15 C16 C11 0.4(3) . . . . ?
N2 C11 C16 N1 -1.0(2) . . . . ?
C12 C11 C16 N1 176.61(18) . . . . ?
N2 C11 C16 C15 179.96(18) . . . . ?
C12 C11 C16 C15 -2.5(3) . . . . ?
C2 C3 C17 O1 -37.4(3) . . . . ?
C4 C3 C17 O1 139.5(2) . . . . ?
C2 C3 C17 C18 140.5(2) . . . . ?
C4 C3 C17 C18 -42.7(3) . . . . ?
O1 C17 C18 C23 150.8(2) . . . . ?
C3 C17 C18 C23 -27.0(3) . . . . ?
O1 C17 C18 C19 -26.9(3) . . . . ?
C3 C17 C18 C19 155.30(19) . . . . ?
C23 C18 C19 C20 0.3(3) . . . . ?
C17 C18 C19 C20 178.0(2) . . . . ?
C18 C19 C20 C21 -1.8(3) . . . . ?
C19 C20 C21 C22 1.0(3) . . . . ?
C19 C20 C21 C24 -179.6(2) . . . . ?
C20 C21 C22 C23 1.4(3) . . . . ?
C24 C21 C22 C23 -178.0(2) . . . . ?
C19 C18 C23 C22 2.1(3) . . . . ?
C17 C18 C23 C22 -175.61(19) . . . . ?
C21 C22 C23 C18 -2.9(3) . . . . ?

_refine_diff_density_max         0.279
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_is_rfmyaa34
_database_code_depnum_ccdc_archive 'CCDC 2164809'
loop_
_audit_author_name
_audit_author_address
'Villinger A.'
;University of Rostock
Germany
;
_audit_update_record             
;
2022-04-06 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

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

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H16 N2 O'
_chemical_formula_sum            'C23 H16 N2 O'
_chemical_formula_weight         336.38

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'
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'

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

# CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   4.4491(2)
_cell_length_b                   19.9827(11)
_cell_length_c                   19.1892(11)
_cell_angle_alpha                90
_cell_angle_beta                 95.304(2)
_cell_angle_gamma                90
_cell_volume                     1698.71(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9951
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      32.19

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.780
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7196
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'

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

# EXPERIMENTAL DATA


_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45700
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.475
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4949
_reflns_number_gt                3856
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

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

# REFINEMENT DATA 

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+0.6731P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4949
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1168
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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

# ATOMIC COORDINATES AND DISPLACEMENT 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8162(2) 0.22472(6) 0.41533(6) 0.0184(2) Uani 1 1 d . . . . .
C2 C 0.9325(3) 0.28631(6) 0.43943(6) 0.0203(2) Uani 1 1 d . . . . .
H2 H 0.8864 0.3047 0.4828 0.024 Uiso 1 1 calc R U . . .
C3 C 1.1182(3) 0.31890(6) 0.39656(6) 0.0240(2) Uani 1 1 d . . . . .
H3 H 1.2017 0.3610 0.4108 0.029 Uiso 1 1 calc R U . . .
C4 C 1.1874(3) 0.29149(7) 0.33232(6) 0.0260(3) Uani 1 1 d . . . . .
H4 H 1.3171 0.3154 0.3046 0.031 Uiso 1 1 calc R U . . .
C5 C 1.0716(3) 0.23084(7) 0.30878(6) 0.0249(2) Uani 1 1 d . . . . .
H5 H 1.1205 0.2125 0.2656 0.030 Uiso 1 1 calc R U . . .
C6 C 0.8790(3) 0.19702(6) 0.35079(6) 0.0204(2) Uani 1 1 d . . . . .
C7 C 0.5798(3) 0.12924(6) 0.39566(6) 0.0203(2) Uani 1 1 d . . . . .
C8 C 0.3836(3) 0.07108(6) 0.40197(7) 0.0249(2) Uani 1 1 d . . . . .
H8 H 0.3643 0.0408 0.3637 0.030 Uiso 1 1 calc R U . . .
C9 C 0.5118(2) 0.18711(5) 0.51281(5) 0.0175(2) Uani 1 1 d . . . . .
H9A H 0.3311 0.1585 0.5150 0.021 Uiso 1 1 calc R U . . .
H9AB H 0.4510 0.2341 0.5199 0.021 Uiso 1 1 calc R U . . .
C10 C 0.7478(2) 0.16723(5) 0.57062(5) 0.0163(2) Uani 1 1 d . . . . .
C11 C 0.8488(3) 0.10131(6) 0.57524(6) 0.0200(2) Uani 1 1 d . . . . .
H11 H 0.7679 0.0694 0.5419 0.024 Uiso 1 1 calc R U . . .
C12 C 1.0658(3) 0.08155(6) 0.62770(6) 0.0247(2) Uani 1 1 d . . . . .
H12 H 1.1318 0.0363 0.6303 0.030 Uiso 1 1 calc R U . . .
C13 C 1.1866(3) 0.12791(7) 0.67644(6) 0.0265(3) Uani 1 1 d . . . . .
H13 H 1.3365 0.1145 0.7122 0.032 Uiso 1 1 calc R U . . .
C14 C 1.0890(3) 0.19341(6) 0.67289(6) 0.0241(2) Uani 1 1 d . . . . .
H14 H 1.1723 0.2250 0.7063 0.029 Uiso 1 1 calc R U . . .
C15 C 0.8678(3) 0.21389(6) 0.62041(6) 0.0188(2) Uani 1 1 d . . . . .
C16 C 0.7665(3) 0.28203(6) 0.62028(6) 0.0223(2) Uani 1 1 d . . . . .
C17 C 0.6856(3) 0.33913(6) 0.62367(6) 0.0254(2) Uani 1 1 d . . . . .
C18 C 0.5920(3) 0.40715(6) 0.63113(6) 0.0249(2) Uani 1 1 d . . . . .
C19 C 0.7074(4) 0.44399(7) 0.68941(7) 0.0335(3) Uani 1 1 d . . . . .
H19 H 0.8500 0.4243 0.7233 0.040 Uiso 1 1 calc R U . . .
C20 C 0.6131(4) 0.50942(7) 0.69768(8) 0.0353(3) Uani 1 1 d . . . . .
H20 H 0.6903 0.5343 0.7375 0.042 Uiso 1 1 calc R U . . .
C21 C 0.4079(3) 0.53865(7) 0.64850(8) 0.0326(3) Uani 1 1 d . . . . .
H21 H 0.3433 0.5834 0.6547 0.039 Uiso 1 1 calc R U . . .
C22 C 0.2975(4) 0.50277(8) 0.59063(9) 0.0444(4) Uani 1 1 d . . . . .
H22 H 0.1583 0.5231 0.5565 0.053 Uiso 1 1 calc R U . . .
C23 C 0.3878(4) 0.43711(7) 0.58177(8) 0.0389(3) Uani 1 1 d . . . . .
H23 H 0.3096 0.4126 0.5417 0.047 Uiso 1 1 calc R U . . .
N1 N 0.6239(2) 0.18040(5) 0.44352(5) 0.01742(19) Uani 1 1 d . . . . .
N2 N 0.7276(2) 0.13730(5) 0.33955(5) 0.0233(2) Uani 1 1 d . . . . .
O1 O 0.2443(2) 0.05807(4) 0.45120(5) 0.0316(2) Uani 1 1 d . . . . .


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

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3761(14) . ?
C1 C2 1.3972(16) . ?
C1 C6 1.4081(15) . ?
C2 C3 1.3818(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.4087(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3768(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.4030(17) . ?
C5 H5 0.9500 . ?
C6 N2 1.3775(16) . ?
C7 N2 1.3225(16) . ?
C7 N1 1.3762(14) . ?
C7 C8 1.4654(17) . ?
C8 O1 1.2050(16) . ?
C8 H8 0.9500 . ?
C9 N1 1.4688(14) . ?
C9 C10 1.5085(15) . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 C11 1.3919(15) . ?
C10 C15 1.4046(15) . ?
C11 C12 1.3863(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.3889(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.3788(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.4025(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.4342(16) . ?
C16 C17 1.2000(17) . ?
C17 C18 1.4328(17) . ?
C18 C23 1.3861(19) . ?
C18 C19 1.3966(17) . ?
C19 C20 1.3866(18) . ?
C19 H19 0.9500 . ?
C20 C21 1.381(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.374(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 131.40(10) . . ?
N1 C1 C6 105.91(10) . . ?
C2 C1 C6 122.67(10) . . ?
C3 C2 C1 116.21(11) . . ?
C3 C2 H2 121.9 . . ?
C1 C2 H2 121.9 . . ?
C2 C3 C4 121.93(12) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 121.60(11) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 117.73(11) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
N2 C6 C5 130.03(11) . . ?
N2 C6 C1 110.13(10) . . ?
C5 C6 C1 119.85(11) . . ?
N2 C7 N1 113.70(10) . . ?
N2 C7 C8 120.58(10) . . ?
N1 C7 C8 125.70(11) . . ?
O1 C8 C7 126.10(11) . . ?
O1 C8 H8 116.9 . . ?
C7 C8 H8 116.9 . . ?
N1 C9 C10 111.72(9) . . ?
N1 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N1 C9 H9AB 109.3 . . ?
C10 C9 H9AB 109.3 . . ?
H9A C9 H9AB 107.9 . . ?
C11 C10 C15 119.00(10) . . ?
C11 C10 C9 119.66(10) . . ?
C15 C10 C9 121.34(10) . . ?
C12 C11 C10 120.99(11) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 119.94(11) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 119.96(11) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.63(11) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C10 119.47(10) . . ?
C14 C15 C16 118.53(10) . . ?
C10 C15 C16 121.98(10) . . ?
C17 C16 C15 176.77(12) . . ?
C16 C17 C18 177.38(13) . . ?
C23 C18 C19 119.26(12) . . ?
C23 C18 C17 121.31(11) . . ?
C19 C18 C17 119.42(12) . . ?
C20 C19 C18 119.72(13) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C21 C20 C19 120.59(13) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C20 119.74(13) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C23 120.43(14) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C18 C23 C22 120.25(13) . . ?
C18 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C1 N1 C7 105.74(9) . . ?
C1 N1 C9 124.93(9) . . ?
C7 N1 C9 129.23(9) . . ?
C7 N2 C6 104.53(9) . . ?

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
N1 C1 C2 C3 -178.71(11) . . . . ?
C6 C1 C2 C3 -0.78(16) . . . . ?
C1 C2 C3 C4 -0.22(17) . . . . ?
C2 C3 C4 C5 0.38(18) . . . . ?
C3 C4 C5 C6 0.46(17) . . . . ?
C4 C5 C6 N2 178.25(11) . . . . ?
C4 C5 C6 C1 -1.43(16) . . . . ?
N1 C1 C6 N2 0.29(12) . . . . ?
C2 C1 C6 N2 -178.09(10) . . . . ?
N1 C1 C6 C5 -179.97(10) . . . . ?
C2 C1 C6 C5 1.65(16) . . . . ?
N2 C7 C8 O1 178.25(12) . . . . ?
N1 C7 C8 O1 -3.7(2) . . . . ?
N1 C9 C10 C11 -64.59(13) . . . . ?
N1 C9 C10 C15 115.73(11) . . . . ?
C15 C10 C11 C12 -0.41(16) . . . . ?
C9 C10 C11 C12 179.90(10) . . . . ?
C10 C11 C12 C13 -0.30(17) . . . . ?
C11 C12 C13 C14 0.48(18) . . . . ?
C12 C13 C14 C15 0.05(18) . . . . ?
C13 C14 C15 C10 -0.75(17) . . . . ?
C13 C14 C15 C16 177.98(11) . . . . ?
C11 C10 C15 C14 0.92(16) . . . . ?
C9 C10 C15 C14 -179.39(10) . . . . ?
C11 C10 C15 C16 -177.77(10) . . . . ?
C9 C10 C15 C16 1.91(16) . . . . ?
C23 C18 C19 C20 1.0(2) . . . . ?
C17 C18 C19 C20 -178.69(13) . . . . ?
C18 C19 C20 C21 -0.6(2) . . . . ?
C19 C20 C21 C22 -0.4(2) . . . . ?
C20 C21 C22 C23 0.8(3) . . . . ?
C19 C18 C23 C22 -0.6(2) . . . . ?
C17 C18 C23 C22 179.11(15) . . . . ?
C21 C22 C23 C18 -0.3(3) . . . . ?
C2 C1 N1 C7 178.01(11) . . . . ?
C6 C1 N1 C7 -0.18(11) . . . . ?
C2 C1 N1 C9 -5.39(18) . . . . ?
C6 C1 N1 C9 176.42(9) . . . . ?
N2 C7 N1 C1 0.02(13) . . . . ?
C8 C7 N1 C1 -178.11(11) . . . . ?
N2 C7 N1 C9 -176.39(10) . . . . ?
C8 C7 N1 C9 5.48(18) . . . . ?
C10 C9 N1 C1 -77.18(13) . . . . ?
C10 C9 N1 C7 98.60(12) . . . . ?
N1 C7 N2 C6 0.16(13) . . . . ?
C8 C7 N2 C6 178.40(10) . . . . ?
C5 C6 N2 C7 -179.98(12) . . . . ?
C1 C6 N2 C7 -0.28(12) . . . . ?

_refine_diff_density_max         0.311
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_av_rfmyd201
_database_code_depnum_ccdc_archive 'CCDC 2164811'
loop_
_audit_author_name
_audit_author_address
'Villinger A.'
;University of Rostock
Germany
;
_audit_update_record             
;
2022-04-06 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

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

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 Br F2 N2'
_chemical_formula_sum            'C14 H9 Br F2 N2'
_chemical_formula_weight         323.14

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

# CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.462
_cell_length_b                   19.539
_cell_length_c                   27.233
_cell_angle_alpha                90
_cell_angle_beta                 93.35
_cell_angle_gamma                90
_cell_volume                     2370.1
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    6058
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      25.45

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.811
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.690
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    3.480
_shelx_estimated_absorpt_T_min   0.197
_shelx_estimated_absorpt_T_max   0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5624
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

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

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Apex Kappa-II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37626
_diffrn_reflns_av_unetI/netI     0.0713
_diffrn_reflns_av_R_equivalents  0.0854
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         3.216
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6269
_reflns_number_gt                4316
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

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

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine. 

 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0194P)²+3.7817P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6269
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.0891
_refine_ls_wR_factor_gt          0.0789
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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

# ATOMIC COORDINATES AND DISPLACEMENT 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_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
Br1 Br 0.44236(9) 0.14776(2) 0.48012(2) 0.02308(10) Uani 1 1 d . . . . .
F1 F 0.9922(5) 0.39561(10) 0.31471(7) 0.0269(5) Uani 1 1 d . . . . .
F2 F 0.8705(5) 0.52819(10) 0.31219(7) 0.0278(5) Uani 1 1 d . . . . .
N1 N 0.3332(6) 0.37894(13) 0.44978(9) 0.0165(6) Uani 1 1 d . . . . .
N2 N 0.2333(7) 0.49189(13) 0.44836(10) 0.0193(6) Uani 1 1 d . . . . .
C1 C 0.1847(8) 0.43293(16) 0.46926(12) 0.0197(7) Uani 1 1 d . . . . .
H1 H 0.0571 0.4280 0.4958 0.024 Uiso 1 1 calc R U . . .
C2 C 0.4943(8) 0.40601(15) 0.41276(11) 0.0157(7) Uani 1 1 d . . . . .
C3 C 0.6861(8) 0.37587(16) 0.38065(11) 0.0184(7) Uani 1 1 d . . . . .
H3 H 0.7321 0.3284 0.3815 0.022 Uiso 1 1 calc R U . . .
C4 C 0.8036(8) 0.41973(17) 0.34766(11) 0.0191(7) Uani 1 1 d . . . . .
C5 C 0.7378(8) 0.48933(16) 0.34633(12) 0.0200(7) Uani 1 1 d . . . . .
C6 C 0.5536(8) 0.51973(16) 0.37798(11) 0.0193(7) Uani 1 1 d . . . . .
H6 H 0.5124 0.5674 0.3769 0.023 Uiso 1 1 calc R U . . .
C7 C 0.4285(8) 0.47640(15) 0.41226(11) 0.0156(7) Uani 1 1 d . . . . .
C8 C 0.3213(8) 0.30709(15) 0.46419(12) 0.0187(7) Uani 1 1 d . . . . .
H8A H 0.3643 0.2783 0.4355 0.022 Uiso 1 1 calc R U . . .
H8B H 0.1152 0.2963 0.4734 0.022 Uiso 1 1 calc R U . . .
C9 C 0.5403(8) 0.28884(16) 0.50672(11) 0.0164(7) Uani 1 1 d . . . . .
C10 C 0.6182(7) 0.22133(15) 0.51721(11) 0.0159(7) Uani 1 1 d . . . . .
C11 C 0.8226(8) 0.20417(17) 0.55552(12) 0.0219(8) Uani 1 1 d . . . . .
H11 H 0.8754 0.1577 0.5613 0.026 Uiso 1 1 calc R U . . .
C12 C 0.9490(9) 0.25506(18) 0.58519(13) 0.0241(8) Uani 1 1 d . . . . .
H12 H 1.0886 0.2437 0.6116 0.029 Uiso 1 1 calc R U . . .
C13 C 0.8714(8) 0.32250(17) 0.57622(12) 0.0226(8) Uani 1 1 d . . . . .
H13 H 0.9569 0.3576 0.5967 0.027 Uiso 1 1 calc R U . . .
C14 C 0.6701(8) 0.33901(15) 0.53767(12) 0.0185(7) Uani 1 1 d . . . . .
H14 H 0.6186 0.3856 0.5320 0.022 Uiso 1 1 calc R U . . .
Br2 Br 0.00257(9) 0.50130(2) 0.06950(2) 0.02667(10) Uani 1 1 d . . . . .
F3 F 0.9208(5) 0.77242(10) 0.28383(8) 0.0317(5) Uani 1 1 d . . . . .
F4 F 0.6596(6) 0.67225(11) 0.32980(7) 0.0375(6) Uani 1 1 d . . . . .
N3 N 0.1099(7) 0.62128(13) 0.17465(10) 0.0184(6) Uani 1 1 d . . . . .
N4 N 0.3127(8) 0.71063(14) 0.13671(10) 0.0283(8) Uani 1 1 d . . . . .
C00B C 0.3038(7) 0.65229(16) 0.20917(12) 0.0163(7) Uani 1 1 d . . . . .
C010 C 0.1284(9) 0.65885(17) 0.13271(13) 0.0268(9) Uani 1 1 d . . . . .
H010 H 0.0161 0.6482 0.1030 0.032 Uiso 1 1 calc R U . . .
C17 C 0.4291(8) 0.70741(16) 0.18519(12) 0.0195(7) Uani 1 1 d . . . . .
C18 C 0.6404(8) 0.74972(17) 0.20971(13) 0.0231(8) Uani 1 1 d . . . . .
H18 H 0.7296 0.7871 0.1937 0.028 Uiso 1 1 calc R U . . .
C19 C 0.7123(8) 0.73488(17) 0.25770(13) 0.0229(8) Uani 1 1 d . . . . .
C20 C 0.5787(9) 0.68114(17) 0.28168(12) 0.0222(8) Uani 1 1 d . . . . .
C21 C 0.3739(8) 0.63806(16) 0.25846(12) 0.0213(8) Uani 1 1 d . . . . .
H21 H 0.2858 0.6010 0.2750 0.026 Uiso 1 1 calc R U . . .
C22 C -0.0552(8) 0.55769(16) 0.17996(13) 0.0209(8) Uani 1 1 d . . . . .
H22A H -0.2252 0.5562 0.1549 0.025 Uiso 1 1 calc R U . . .
H22B H -0.1391 0.5566 0.2128 0.025 Uiso 1 1 calc R U . . .
C23 C 0.1403(8) 0.49518(16) 0.17417(11) 0.0169(7) Uani 1 1 d . . . . .
C24 C 0.1915(8) 0.46649(16) 0.12870(12) 0.0200(7) Uani 1 1 d . . . . .
C25 C 0.3789(8) 0.41050(17) 0.12452(13) 0.0227(8) Uani 1 1 d . . . . .
H25 H 0.4102 0.3917 0.0931 0.027 Uiso 1 1 calc R U . . .
C26 C 0.5200(9) 0.38217(17) 0.16614(13) 0.0251(8) Uani 1 1 d . . . . .
H26 H 0.6506 0.3441 0.1634 0.030 Uiso 1 1 calc R U . . .
C27 C 0.4714(9) 0.40904(17) 0.21153(13) 0.0261(8) Uani 1 1 d . . . . .
H27 H 0.5679 0.3894 0.2402 0.031 Uiso 1 1 calc R U . . .
C28 C 0.2820(8) 0.46469(16) 0.21569(12) 0.0215(8) Uani 1 1 d . . . . .
H28 H 0.2480 0.4824 0.2474 0.026 Uiso 1 1 calc R U . . .


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

# MOLECULAR GEOMETRY

_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
Br1 C10 1.900(3) . ?
F1 C4 1.350(4) . ?
F2 C5 1.362(4) . ?
N1 C1 1.369(4) . ?
N1 C2 1.378(4) . ?
N1 C8 1.459(4) . ?
N2 C1 1.309(4) . ?
N2 C7 1.385(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.390(5) . ?
C2 C7 1.406(4) . ?
C3 C4 1.368(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(4) . ?
C5 C6 1.362(5) . ?
C6 C7 1.400(4) . ?
C6 H6 0.9500 . ?
C8 C9 1.514(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.390(4) . ?
C9 C14 1.396(4) . ?
C10 C11 1.386(5) . ?
C11 C12 1.381(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
Br2 C24 1.901(3) . ?
F3 C19 1.354(4) . ?
F4 C20 1.350(4) . ?
N3 C010 1.364(4) . ?
N3 C00B 1.380(4) . ?
N3 C22 1.456(4) . ?
N4 C010 1.304(5) . ?
N4 C17 1.392(4) . ?
C00B C21 1.389(4) . ?
C00B C17 1.393(4) . ?
C010 H010 0.9500 . ?
C17 C18 1.394(5) . ?
C18 C19 1.359(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.389(5) . ?
C20 C21 1.370(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.515(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.390(4) . ?
C23 C28 1.396(5) . ?
C24 C25 1.386(5) . ?
C25 C26 1.380(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.372(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.386(5) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 105.8(3) . . ?
C1 N1 C8 127.7(3) . . ?
C2 N1 C8 126.5(3) . . ?
C1 N2 C7 104.1(3) . . ?
N2 C1 N1 114.4(3) . . ?
N2 C1 H1 122.8 . . ?
N1 C1 H1 122.8 . . ?
N1 C2 C3 131.7(3) . . ?
N1 C2 C7 105.4(3) . . ?
C3 C2 C7 123.0(3) . . ?
C4 C3 C2 114.9(3) . . ?
C4 C3 H3 122.5 . . ?
C2 C3 H3 122.5 . . ?
F1 C4 C3 119.7(3) . . ?
F1 C4 C5 117.6(3) . . ?
C3 C4 C5 122.7(3) . . ?
C6 C5 F2 119.4(3) . . ?
C6 C5 C4 123.0(3) . . ?
F2 C5 C4 117.6(3) . . ?
C5 C6 C7 115.9(3) . . ?
C5 C6 H6 122.0 . . ?
C7 C6 H6 122.0 . . ?
N2 C7 C6 129.3(3) . . ?
N2 C7 C2 110.3(3) . . ?
C6 C7 C2 120.4(3) . . ?
N1 C8 C9 113.6(3) . . ?
N1 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
N1 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C14 116.9(3) . . ?
C10 C9 C8 121.6(3) . . ?
C14 C9 C8 121.5(3) . . ?
C11 C10 C9 122.0(3) . . ?
C11 C10 Br1 116.8(2) . . ?
C9 C10 Br1 121.2(2) . . ?
C12 C11 C10 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C9 121.6(3) . . ?
C13 C14 H14 119.2 . . ?
C9 C14 H14 119.2 . . ?
C010 N3 C00B 105.5(3) . . ?
C010 N3 C22 126.7(3) . . ?
C00B N3 C22 127.4(3) . . ?
C010 N4 C17 104.1(3) . . ?
N3 C00B C21 131.9(3) . . ?
N3 C00B C17 105.8(3) . . ?
C21 C00B C17 122.3(3) . . ?
N4 C010 N3 114.6(3) . . ?
N4 C010 H010 122.7 . . ?
N3 C010 H010 122.7 . . ?
N4 C17 C00B 110.0(3) . . ?
N4 C17 C18 129.2(3) . . ?
C00B C17 C18 120.8(3) . . ?
C19 C18 C17 116.7(3) . . ?
C19 C18 H18 121.7 . . ?
C17 C18 H18 121.7 . . ?
F3 C19 C18 120.4(3) . . ?
F3 C19 C20 117.6(3) . . ?
C18 C19 C20 122.0(3) . . ?
F4 C20 C21 120.2(3) . . ?
F4 C20 C19 117.1(3) . . ?
C21 C20 C19 122.7(3) . . ?
C20 C21 C00B 115.4(3) . . ?
C20 C21 H21 122.3 . . ?
C00B C21 H21 122.3 . . ?
N3 C22 C23 112.3(3) . . ?
N3 C22 H22A 109.1 . . ?
C23 C22 H22A 109.1 . . ?
N3 C22 H22B 109.1 . . ?
C23 C22 H22B 109.1 . . ?
H22A C22 H22B 107.9 . . ?
C24 C23 C28 117.3(3) . . ?
C24 C23 C22 122.9(3) . . ?
C28 C23 C22 119.7(3) . . ?
C25 C24 C23 121.5(3) . . ?
C25 C24 Br2 116.9(3) . . ?
C23 C24 Br2 121.6(3) . . ?
C26 C25 C24 119.9(3) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C27 C26 C25 119.9(3) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C26 C27 C28 120.2(3) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C27 C28 C23 121.2(3) . . ?
C27 C28 H28 119.4 . . ?
C23 C28 H28 119.4 . . ?

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
C7 N2 C1 N1 0.0(4) . . . . ?
C2 N1 C1 N2 0.3(4) . . . . ?
C8 N1 C1 N2 -178.7(3) . . . . ?
C1 N1 C2 C3 179.6(4) . . . . ?
C8 N1 C2 C3 -1.4(6) . . . . ?
C1 N1 C2 C7 -0.4(3) . . . . ?
C8 N1 C2 C7 178.6(3) . . . . ?
N1 C2 C3 C4 179.0(3) . . . . ?
C7 C2 C3 C4 -1.1(5) . . . . ?
C2 C3 C4 F1 -179.8(3) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
F1 C4 C5 C6 -179.3(3) . . . . ?
C3 C4 C5 C6 0.7(6) . . . . ?
F1 C4 C5 F2 -0.6(5) . . . . ?
C3 C4 C5 F2 179.3(3) . . . . ?
F2 C5 C6 C7 -179.4(3) . . . . ?
C4 C5 C6 C7 -0.7(5) . . . . ?
C1 N2 C7 C6 179.1(3) . . . . ?
C1 N2 C7 C2 -0.2(4) . . . . ?
C5 C6 C7 N2 -179.3(3) . . . . ?
C5 C6 C7 C2 -0.1(5) . . . . ?
N1 C2 C7 N2 0.4(4) . . . . ?
C3 C2 C7 N2 -179.6(3) . . . . ?
N1 C2 C7 C6 -179.0(3) . . . . ?
C3 C2 C7 C6 1.0(5) . . . . ?
C1 N1 C8 C9 -85.7(4) . . . . ?
C2 N1 C8 C9 95.5(4) . . . . ?
N1 C8 C9 C10 -162.9(3) . . . . ?
N1 C8 C9 C14 18.0(5) . . . . ?
C14 C9 C10 C11 -2.1(5) . . . . ?
C8 C9 C10 C11 178.8(3) . . . . ?
C14 C9 C10 Br1 176.8(2) . . . . ?
C8 C9 C10 Br1 -2.4(5) . . . . ?
C9 C10 C11 C12 1.6(5) . . . . ?
Br1 C10 C11 C12 -177.3(3) . . . . ?
C10 C11 C12 C13 -0.3(6) . . . . ?
C11 C12 C13 C14 -0.4(6) . . . . ?
C12 C13 C14 C9 -0.2(6) . . . . ?
C10 C9 C14 C13 1.4(5) . . . . ?
C8 C9 C14 C13 -179.5(3) . . . . ?
C010 N3 C00B C21 178.3(4) . . . . ?
C22 N3 C00B C21 -7.8(6) . . . . ?
C010 N3 C00B C17 -0.2(4) . . . . ?
C22 N3 C00B C17 173.8(3) . . . . ?
C17 N4 C010 N3 0.4(4) . . . . ?
C00B N3 C010 N4 -0.1(4) . . . . ?
C22 N3 C010 N4 -174.2(3) . . . . ?
C010 N4 C17 C00B -0.5(4) . . . . ?
C010 N4 C17 C18 179.1(4) . . . . ?
N3 C00B C17 N4 0.4(4) . . . . ?
C21 C00B C17 N4 -178.2(3) . . . . ?
N3 C00B C17 C18 -179.2(3) . . . . ?
C21 C00B C17 C18 2.1(5) . . . . ?
N4 C17 C18 C19 179.5(3) . . . . ?
C00B C17 C18 C19 -0.9(5) . . . . ?
C17 C18 C19 F3 178.4(3) . . . . ?
C17 C18 C19 C20 -1.2(5) . . . . ?
F3 C19 C20 F4 2.4(5) . . . . ?
C18 C19 C20 F4 -177.9(3) . . . . ?
F3 C19 C20 C21 -177.3(3) . . . . ?
C18 C19 C20 C21 2.3(6) . . . . ?
F4 C20 C21 C00B 179.2(3) . . . . ?
C19 C20 C21 C00B -1.0(5) . . . . ?
N3 C00B C21 C20 -179.4(3) . . . . ?
C17 C00B C21 C20 -1.1(5) . . . . ?
C010 N3 C22 C23 94.3(4) . . . . ?
C00B N3 C22 C23 -78.4(4) . . . . ?
N3 C22 C23 C24 -85.5(4) . . . . ?
N3 C22 C23 C28 93.4(4) . . . . ?
C28 C23 C24 C25 -0.9(5) . . . . ?
C22 C23 C24 C25 178.0(3) . . . . ?
C28 C23 C24 Br2 178.1(2) . . . . ?
C22 C23 C24 Br2 -3.0(5) . . . . ?
C23 C24 C25 C26 -0.2(5) . . . . ?
Br2 C24 C25 C26 -179.2(3) . . . . ?
C24 C25 C26 C27 0.8(5) . . . . ?
C25 C26 C27 C28 -0.3(6) . . . . ?
C26 C27 C28 C23 -0.9(6) . . . . ?
C24 C23 C28 C27 1.4(5) . . . . ?
C22 C23 C28 C27 -177.5(3) . . . . ?

_refine_diff_density_max         0.495
_refine_diff_density_min         -0.892
_refine_diff_density_rms         0.109

####################################################################### 
# 
# 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_is_rfmyca43
_database_code_depnum_ccdc_archive 'CCDC 2164813'
loop_
_audit_author_name
_audit_author_address
'Villinger A.'
;University of Rostock
Germany
;
_audit_update_record             
;
2022-04-06 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

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

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 N2 O'
_chemical_formula_sum            'C20 H16 N2 O'
_chemical_formula_weight         300.35

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'
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'

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

# CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   8.2236(4)
_cell_length_b                   13.2218(7)
_cell_length_c                   14.5288(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.306(2)
_cell_angle_gamma                90
_cell_volume                     1543.43(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9279
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      29.94

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6701
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'

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

# EXPERIMENTAL DATA


_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23823
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.105
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4085
_reflns_number_gt                2898
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

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

# REFINEMENT DATA 

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0474P)²+1.0229P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4085
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1266
_refine_ls_wR_factor_gt          0.1093
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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

# ATOMIC COORDINATES AND DISPLACEMENT 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.41593(17) 0.31921(9) 0.73423(9) 0.0317(3) Uani 1 1 d . . . . .
N1 N 0.14966(17) 0.57080(10) 0.39372(10) 0.0234(3) Uani 1 1 d . . . . .
N2 N 0.08456(15) 0.40681(9) 0.39377(9) 0.0187(3) Uani 1 1 d . . . . .
C1 C 0.32905(18) 0.39446(11) 0.58449(11) 0.0180(3) Uani 1 1 d . . . . .
C2 C 0.35260(19) 0.29818(11) 0.53606(11) 0.0181(3) Uani 1 1 d . . . . .
C3 C 0.5067(2) 0.24880(12) 0.56080(12) 0.0227(3) Uani 1 1 d . . . . .
H3 H 0.5920 0.2769 0.6085 0.027 Uiso 1 1 calc R U . . .
C4 C 0.5366(2) 0.15969(12) 0.51683(13) 0.0256(4) Uani 1 1 d . . . . .
H4 H 0.6418 0.1273 0.5343 0.031 Uiso 1 1 calc R U . . .
C5 C 0.4129(2) 0.11778(12) 0.44730(12) 0.0235(3) Uani 1 1 d . . . . .
H5 H 0.4324 0.0560 0.4181 0.028 Uiso 1 1 calc R U . . .
C6 C 0.2607(2) 0.16630(11) 0.42056(11) 0.0202(3) Uani 1 1 d . . . . .
H6 H 0.1770 0.1382 0.3720 0.024 Uiso 1 1 calc R U . . .
C7 C 0.22934(18) 0.25591(11) 0.46421(11) 0.0176(3) Uani 1 1 d . . . . .
C8 C 0.06287(19) 0.30749(11) 0.43369(11) 0.0198(3) Uani 1 1 d . . . . .
H8A H -0.0112 0.2654 0.3861 0.024 Uiso 1 1 calc R U . . .
H8AB H 0.0102 0.3154 0.4885 0.024 Uiso 1 1 calc R U . . .
C9 C 0.0197(2) 0.44217(13) 0.30467(11) 0.0236(3) Uani 1 1 d . . . . .
H9 H -0.0415 0.4050 0.2528 0.028 Uiso 1 1 calc R U . . .
C10 C 0.0620(2) 0.54231(13) 0.30643(12) 0.0261(4) Uani 1 1 d . . . . .
H10 H 0.0342 0.5865 0.2539 0.031 Uiso 1 1 calc R U . . .
C11 C 0.16315(18) 0.48621(11) 0.44488(11) 0.0184(3) Uani 1 1 d . . . . .
C12 C 0.24970(19) 0.47722(11) 0.54215(11) 0.0191(3) Uani 1 1 d . . . . .
H12 H 0.2510 0.5356 0.5804 0.023 Uiso 1 1 calc R U . . .
C13 C 0.39852(19) 0.39805(12) 0.68893(11) 0.0207(3) Uani 1 1 d . . . . .
C14 C 0.44356(19) 0.49777(12) 0.73683(11) 0.0197(3) Uani 1 1 d . . . . .
C15 C 0.5348(2) 0.56798(12) 0.69593(12) 0.0236(3) Uani 1 1 d . . . . .
H15 H 0.5621 0.5530 0.6371 0.028 Uiso 1 1 calc R U . . .
C16 C 0.5857(2) 0.65910(13) 0.74044(13) 0.0299(4) Uani 1 1 d . . . . .
H16 H 0.6502 0.7054 0.7132 0.036 Uiso 1 1 calc R U . . .
C17 C 0.5418(2) 0.68191(13) 0.82454(13) 0.0311(4) Uani 1 1 d . . . . .
H17 H 0.5745 0.7446 0.8547 0.037 Uiso 1 1 calc R U . . .
C18 C 0.4500(2) 0.61359(13) 0.86521(12) 0.0259(4) Uani 1 1 d . . . . .
H18 H 0.4188 0.6310 0.9225 0.031 Uiso 1 1 calc R U . . .
C19 C 0.40243(19) 0.51967(12) 0.82375(11) 0.0209(3) Uani 1 1 d . . . . .
C20 C 0.3078(2) 0.44893(14) 0.87405(12) 0.0284(4) Uani 1 1 d . . . . .
H20A H 0.2415 0.4024 0.8285 0.043 Uiso 1 1 calc R U . . .
H20B H 0.2340 0.4880 0.9053 0.043 Uiso 1 1 calc R U . . .
H20C H 0.3864 0.4102 0.9212 0.043 Uiso 1 1 calc R U . . .


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

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.2248(19) . ?
N1 C11 1.3344(19) . ?
N1 C10 1.371(2) . ?
N2 C11 1.3663(19) . ?
N2 C9 1.373(2) . ?
N2 C8 1.4617(19) . ?
C1 C12 1.353(2) . ?
C1 C2 1.487(2) . ?
C1 C13 1.504(2) . ?
C2 C3 1.403(2) . ?
C2 C7 1.407(2) . ?
C3 C4 1.387(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.509(2) . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 C10 1.368(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.445(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.500(2) . ?
C14 C15 1.403(2) . ?
C14 C19 1.405(2) . ?
C15 C16 1.389(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.399(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.502(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 C10 104.47(13) . . ?
C11 N2 C9 107.12(13) . . ?
C11 N2 C8 123.93(13) . . ?
C9 N2 C8 128.65(13) . . ?
C12 C1 C2 125.17(14) . . ?
C12 C1 C13 118.42(13) . . ?
C2 C1 C13 116.40(13) . . ?
C3 C2 C7 118.31(14) . . ?
C3 C2 C1 118.60(14) . . ?
C7 C2 C1 123.05(13) . . ?
C4 C3 C2 121.09(15) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 120.02(15) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.83(14) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 120.64(14) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C2 120.10(14) . . ?
C6 C7 C8 119.67(14) . . ?
C2 C7 C8 120.24(13) . . ?
N2 C8 C7 110.05(12) . . ?
N2 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
N2 C8 H8AB 109.7 . . ?
C7 C8 H8AB 109.7 . . ?
H8A C8 H8AB 108.2 . . ?
C10 C9 N2 105.43(14) . . ?
C10 C9 H9 127.3 . . ?
N2 C9 H9 127.3 . . ?
C9 C10 N1 111.38(14) . . ?
C9 C10 H10 124.3 . . ?
N1 C10 H10 124.3 . . ?
N1 C11 N2 111.58(13) . . ?
N1 C11 C12 125.36(14) . . ?
N2 C11 C12 123.06(13) . . ?
C1 C12 C11 126.89(14) . . ?
C1 C12 H12 116.6 . . ?
C11 C12 H12 116.6 . . ?
O1 C13 C14 120.65(14) . . ?
O1 C13 C1 119.42(14) . . ?
C14 C13 C1 119.93(13) . . ?
C15 C14 C19 119.82(14) . . ?
C15 C14 C13 119.11(14) . . ?
C19 C14 C13 121.00(14) . . ?
C16 C15 C14 120.79(16) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C16 C15 119.51(16) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 120.25(16) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C19 121.47(16) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C18 C19 C14 118.10(15) . . ?
C18 C19 C20 118.01(15) . . ?
C14 C19 C20 123.89(15) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 C1 C2 C3 138.69(17) . . . . ?
C13 C1 C2 C3 -41.9(2) . . . . ?
C12 C1 C2 C7 -39.1(2) . . . . ?
C13 C1 C2 C7 140.28(15) . . . . ?
C7 C2 C3 C4 -1.0(2) . . . . ?
C1 C2 C3 C4 -178.90(15) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 1.3(3) . . . . ?
C4 C5 C6 C7 -1.3(2) . . . . ?
C5 C6 C7 C2 0.1(2) . . . . ?
C5 C6 C7 C8 179.82(15) . . . . ?
C3 C2 C7 C6 1.0(2) . . . . ?
C1 C2 C7 C6 178.84(14) . . . . ?
C3 C2 C7 C8 -178.68(14) . . . . ?
C1 C2 C7 C8 -0.9(2) . . . . ?
C11 N2 C8 C7 -67.51(18) . . . . ?
C9 N2 C8 C7 119.61(16) . . . . ?
C6 C7 C8 N2 -116.43(15) . . . . ?
C2 C7 C8 N2 63.30(18) . . . . ?
C11 N2 C9 C10 -0.30(17) . . . . ?
C8 N2 C9 C10 173.52(15) . . . . ?
N2 C9 C10 N1 -0.52(19) . . . . ?
C11 N1 C10 C9 1.13(19) . . . . ?
C10 N1 C11 N2 -1.32(18) . . . . ?
C10 N1 C11 C12 178.46(15) . . . . ?
C9 N2 C11 N1 1.05(18) . . . . ?
C8 N2 C11 N1 -173.14(13) . . . . ?
C9 N2 C11 C12 -178.74(14) . . . . ?
C8 N2 C11 C12 7.1(2) . . . . ?
C2 C1 C12 C11 4.8(3) . . . . ?
C13 C1 C12 C11 -174.59(14) . . . . ?
N1 C11 C12 C1 -148.90(17) . . . . ?
N2 C11 C12 C1 30.9(2) . . . . ?
C12 C1 C13 O1 154.02(16) . . . . ?
C2 C1 C13 O1 -25.4(2) . . . . ?
C12 C1 C13 C14 -25.1(2) . . . . ?
C2 C1 C13 C14 155.44(14) . . . . ?
O1 C13 C14 C15 134.95(17) . . . . ?
C1 C13 C14 C15 -45.9(2) . . . . ?
O1 C13 C14 C19 -42.1(2) . . . . ?
C1 C13 C14 C19 137.05(15) . . . . ?
C19 C14 C15 C16 0.2(2) . . . . ?
C13 C14 C15 C16 -176.91(15) . . . . ?
C14 C15 C16 C17 -1.8(3) . . . . ?
C15 C16 C17 C18 1.1(3) . . . . ?
C16 C17 C18 C19 1.3(3) . . . . ?
C17 C18 C19 C14 -2.9(2) . . . . ?
C17 C18 C19 C20 178.11(16) . . . . ?
C15 C14 C19 C18 2.2(2) . . . . ?
C13 C14 C19 C18 179.18(14) . . . . ?
C15 C14 C19 C20 -178.92(15) . . . . ?
C13 C14 C19 C20 -1.9(2) . . . . ?

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_is_rfmyaa43
_database_code_depnum_ccdc_archive 'CCDC 2164814'
loop_
_audit_author_name
_audit_author_address
'Villinger A.'
;University of Rostock
Germany
;
_audit_update_record             
;
2022-04-06 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

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

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H16 N2 O'
_chemical_formula_sum            'C23 H16 N2 O'
_chemical_formula_weight         336.38

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'
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'

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

# CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   11.034(2)
_cell_length_b                   14.502(3)
_cell_length_c                   11.291(2)
_cell_angle_alpha                90
_cell_angle_beta                 117.137(5)
_cell_angle_gamma                90
_cell_volume                     1607.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2498
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      32.92

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6442
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

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

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Apex Kappa-II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10259
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.493
_diffrn_reflns_theta_max         27.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3800
_reflns_number_gt                2905
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

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

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine. 

 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0519P)²+0.5328P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3800
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1281
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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

# ATOMIC COORDINATES AND DISPLACEMENT 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.10937(13) 0.48105(8) 0.24087(11) 0.0284(3) Uani 1 1 d . . . . .
N1 N 0.51081(14) 0.46665(9) 0.69747(12) 0.0204(3) Uani 1 1 d . . . . .
N2 N 0.41282(13) 0.59440(9) 0.72948(12) 0.0170(3) Uani 1 1 d . . . . .
C1 C 0.41409(16) 0.52961(11) 0.64153(14) 0.0182(3) Uani 1 1 d . . . . .
C2 C 0.32305(16) 0.53228(11) 0.50046(14) 0.0187(3) Uani 1 1 d . . . . .
H2 H 0.3549 0.5025 0.4450 0.022 Uiso 1 1 calc R U . . .
C3 C 0.19925(16) 0.57139(11) 0.43732(14) 0.0173(3) Uani 1 1 d . . . . .
C4 C 0.12095(16) 0.61553(10) 0.49849(14) 0.0173(3) Uani 1 1 d . . . . .
C5 C -0.02141(16) 0.60821(11) 0.43263(15) 0.0212(3) Uani 1 1 d . . . . .
H5 H -0.0640 0.5785 0.3484 0.025 Uiso 1 1 calc R U . . .
C6 C -0.10101(17) 0.64309(12) 0.48726(16) 0.0246(4) Uani 1 1 d . . . . .
H6 H -0.1973 0.6379 0.4404 0.029 Uiso 1 1 calc R U . . .
C7 C -0.04026(17) 0.68577(12) 0.61070(16) 0.0247(4) Uani 1 1 d . . . . .
H7 H -0.0946 0.7092 0.6492 0.030 Uiso 1 1 calc R U . . .
C8 C 0.10017(17) 0.69396(11) 0.67739(15) 0.0216(3) Uani 1 1 d . . . . .
H8 H 0.1416 0.7228 0.7623 0.026 Uiso 1 1 calc R U . . .
C9 C 0.18188(15) 0.66080(10) 0.62252(14) 0.0176(3) Uani 1 1 d . . . . .
C10 C 0.33292(15) 0.67897(11) 0.69160(14) 0.0188(3) Uani 1 1 d . . . . .
H10A H 0.3580 0.7152 0.6317 0.023 Uiso 1 1 calc R U . . .
H10B H 0.3555 0.7164 0.7723 0.023 Uiso 1 1 calc R U . . .
C11 C 0.51932(15) 0.57267(11) 0.85159(14) 0.0176(3) Uani 1 1 d . . . . .
C12 C 0.56867(16) 0.61497(11) 0.97530(14) 0.0207(3) Uani 1 1 d . . . . .
H12 H 0.5287 0.6695 0.9884 0.025 Uiso 1 1 calc R U . . .
C13 C 0.67903(16) 0.57331(12) 1.07819(15) 0.0239(4) Uani 1 1 d . . . . .
H13 H 0.7161 0.6002 1.1643 0.029 Uiso 1 1 calc R U . . .
C14 C 0.73802(16) 0.49255(12) 1.05946(15) 0.0234(4) Uani 1 1 d . . . . .
H14 H 0.8139 0.4661 1.1330 0.028 Uiso 1 1 calc R U . . .
C15 C 0.68819(16) 0.45073(12) 0.93655(15) 0.0215(3) Uani 1 1 d . . . . .
H15 H 0.7278 0.3957 0.9243 0.026 Uiso 1 1 calc R U . . .
C16 C 0.57730(15) 0.49216(11) 0.83041(14) 0.0181(3) Uani 1 1 d . . . . .
C17 C 0.12957(16) 0.55815(11) 0.28785(14) 0.0187(3) Uani 1 1 d . . . . .
C18 C 0.09598(15) 0.64142(11) 0.20079(14) 0.0166(3) Uani 1 1 d . . . . .
C19 C 0.01401(16) 0.63066(11) 0.06386(14) 0.0193(3) Uani 1 1 d . . . . .
H19 H -0.0293 0.5733 0.0294 0.023 Uiso 1 1 calc R U . . .
C20 C -0.00380(16) 0.70353(12) -0.02080(15) 0.0218(3) Uani 1 1 d . . . . .
H20 H -0.0593 0.6961 -0.1138 0.026 Uiso 1 1 calc R U . . .
C21 C 0.05885(16) 0.78789(12) 0.02882(15) 0.0234(4) Uani 1 1 d . . . . .
H21 H 0.0470 0.8376 -0.0303 0.028 Uiso 1 1 calc R U . . .
C22 C 0.13890(16) 0.79941(11) 0.16519(16) 0.0224(3) Uani 1 1 d . . . . .
H22 H 0.1814 0.8570 0.1995 0.027 Uiso 1 1 calc R U . . .
C23 C 0.15620(16) 0.72628(11) 0.25066(15) 0.0194(3) Uani 1 1 d . . . . .
H23 H 0.2095 0.7343 0.3439 0.023 Uiso 1 1 calc R U . . .


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

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C17 1.2139(19) . ?
N1 C1 1.325(2) . ?
N1 C16 1.3869(19) . ?
N2 C1 1.3717(19) . ?
N2 C11 1.3795(18) . ?
N2 C10 1.4562(19) . ?
C1 C2 1.445(2) . ?
C2 C3 1.345(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.476(2) . ?
C3 C17 1.514(2) . ?
C4 C5 1.402(2) . ?
C4 C9 1.409(2) . ?
C5 C6 1.379(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.385(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.392(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.506(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.389(2) . ?
C11 C16 1.403(2) . ?
C12 C13 1.381(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.402(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.399(2) . ?
C15 H15 0.9500 . ?
C17 C18 1.493(2) . ?
C18 C23 1.390(2) . ?
C18 C19 1.399(2) . ?
C19 C20 1.378(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.391(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.392(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C16 104.21(13) . . ?
C1 N2 C11 106.36(13) . . ?
C1 N2 C10 124.68(12) . . ?
C11 N2 C10 127.70(13) . . ?
N1 C1 N2 113.50(13) . . ?
N1 C1 C2 123.20(14) . . ?
N2 C1 C2 123.23(14) . . ?
C3 C2 C1 128.55(15) . . ?
C3 C2 H2 115.7 . . ?
C1 C2 H2 115.7 . . ?
C2 C3 C4 127.23(13) . . ?
C2 C3 C17 114.46(14) . . ?
C4 C3 C17 117.95(13) . . ?
C5 C4 C9 118.27(15) . . ?
C5 C4 C3 118.19(13) . . ?
C9 C4 C3 123.47(14) . . ?
C6 C5 C4 121.53(15) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 119.92(15) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 119.53(16) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 121.31(15) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C4 119.41(14) . . ?
C8 C9 C10 119.83(14) . . ?
C4 C9 C10 120.65(14) . . ?
N2 C10 C9 112.54(12) . . ?
N2 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
N2 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
N2 C11 C12 131.96(15) . . ?
N2 C11 C16 105.45(13) . . ?
C12 C11 C16 122.59(14) . . ?
C13 C12 C11 116.33(15) . . ?
C13 C12 H12 121.8 . . ?
C11 C12 H12 121.8 . . ?
C12 C13 C14 122.04(15) . . ?
C12 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C15 C14 C13 121.33(14) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 117.70(15) . . ?
C14 C15 H15 121.1 . . ?
C16 C15 H15 121.1 . . ?
N1 C16 C15 129.56(15) . . ?
N1 C16 C11 110.43(13) . . ?
C15 C16 C11 120.00(14) . . ?
O1 C17 C18 121.09(13) . . ?
O1 C17 C3 120.17(14) . . ?
C18 C17 C3 118.59(13) . . ?
C23 C18 C19 119.68(14) . . ?
C23 C18 C17 121.34(13) . . ?
C19 C18 C17 118.59(14) . . ?
C20 C19 C18 119.80(15) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 120.52(14) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C22 119.94(15) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 119.61(15) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C18 120.43(14) . . ?
C22 C23 H23 119.8 . . ?
C18 C23 H23 119.8 . . ?

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
C16 N1 C1 N2 -0.22(18) . . . . ?
C16 N1 C1 C2 176.95(15) . . . . ?
C11 N2 C1 N1 1.41(18) . . . . ?
C10 N2 C1 N1 169.43(14) . . . . ?
C11 N2 C1 C2 -175.76(15) . . . . ?
C10 N2 C1 C2 -7.7(2) . . . . ?
N1 C1 C2 C3 157.50(17) . . . . ?
N2 C1 C2 C3 -25.6(3) . . . . ?
C1 C2 C3 C4 -5.1(3) . . . . ?
C1 C2 C3 C17 -178.01(15) . . . . ?
C2 C3 C4 C5 -146.47(16) . . . . ?
C17 C3 C4 C5 26.2(2) . . . . ?
C2 C3 C4 C9 30.4(3) . . . . ?
C17 C3 C4 C9 -156.93(14) . . . . ?
C9 C4 C5 C6 -0.8(2) . . . . ?
C3 C4 C5 C6 176.27(15) . . . . ?
C4 C5 C6 C7 -0.6(2) . . . . ?
C5 C6 C7 C8 0.8(2) . . . . ?
C6 C7 C8 C9 0.5(2) . . . . ?
C7 C8 C9 C4 -1.9(2) . . . . ?
C7 C8 C9 C10 174.12(14) . . . . ?
C5 C4 C9 C8 2.0(2) . . . . ?
C3 C4 C9 C8 -174.85(14) . . . . ?
C5 C4 C9 C10 -173.99(14) . . . . ?
C3 C4 C9 C10 9.1(2) . . . . ?
C1 N2 C10 C9 63.5(2) . . . . ?
C11 N2 C10 C9 -131.05(16) . . . . ?
C8 C9 C10 N2 119.78(15) . . . . ?
C4 C9 C10 N2 -64.23(18) . . . . ?
C1 N2 C11 C12 178.17(17) . . . . ?
C10 N2 C11 C12 10.6(3) . . . . ?
C1 N2 C11 C16 -1.93(17) . . . . ?
C10 N2 C11 C16 -169.48(15) . . . . ?
N2 C11 C12 C13 179.74(16) . . . . ?
C16 C11 C12 C13 -0.1(2) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C13 C14 C15 C16 0.6(2) . . . . ?
C1 N1 C16 C15 -179.92(17) . . . . ?
C1 N1 C16 C11 -1.06(18) . . . . ?
C14 C15 C16 N1 177.75(16) . . . . ?
C14 C15 C16 C11 -1.0(2) . . . . ?
N2 C11 C16 N1 1.90(18) . . . . ?
C12 C11 C16 N1 -178.19(15) . . . . ?
N2 C11 C16 C15 -179.11(14) . . . . ?
C12 C11 C16 C15 0.8(2) . . . . ?
C2 C3 C17 O1 57.3(2) . . . . ?
C4 C3 C17 O1 -116.31(18) . . . . ?
C2 C3 C17 C18 -118.32(16) . . . . ?
C4 C3 C17 C18 68.09(19) . . . . ?
O1 C17 C18 C23 -158.96(16) . . . . ?
C3 C17 C18 C23 16.6(2) . . . . ?
O1 C17 C18 C19 13.9(2) . . . . ?
C3 C17 C18 C19 -170.58(14) . . . . ?
C23 C18 C19 C20 1.5(2) . . . . ?
C17 C18 C19 C20 -171.40(15) . . . . ?
C18 C19 C20 C21 -0.2(2) . . . . ?
C19 C20 C21 C22 -0.8(2) . . . . ?
C20 C21 C22 C23 0.4(2) . . . . ?
C21 C22 C23 C18 1.0(2) . . . . ?
C19 C18 C23 C22 -2.0(2) . . . . ?
C17 C18 C23 C22 170.76(15) . . . . ?

_refine_diff_density_max         0.331
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_is_rfmydc41
_database_code_depnum_ccdc_archive 'CCDC 2164815'
loop_
_audit_author_name
_audit_author_address
'Villinger A.'
;University of Rostock
Germany
;
_audit_update_record             
;
2022-04-06 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

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

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H16 F2 N2 O2'
_chemical_formula_sum            'C24 H16 F2 N2 O2'
_chemical_formula_weight         402.39

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'

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

# CRYSTAL DATA

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.225(2)
_cell_length_b                   10.669(2)
_cell_length_c                   20.170(4)
_cell_angle_alpha                91.526(6)
_cell_angle_beta                 102.762(6)
_cell_angle_gamma                90.111(6)
_cell_volume                     1935.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4995
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      32.57

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6843
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

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

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Apex Kappa-II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29228
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.910
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9333
_reflns_number_gt                5159
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

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

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine. 

 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0610P)²+0.1306P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9333
_refine_ls_number_parameters     543
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1445
_refine_ls_wR_factor_gt          0.1184
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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

# ATOMIC COORDINATES AND DISPLACEMENT 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_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 -0.07767(12) 1.07336(9) 0.82914(6) 0.0482(3) Uani 1 1 d . . . . .
F2 F -0.05185(12) 0.93893(10) 0.71987(6) 0.0500(3) Uani 1 1 d . . . . .
O1 O 0.59399(16) 0.59037(13) 0.96500(7) 0.0477(4) Uani 1 1 d . . . . .
O2 O 0.26238(16) 0.83717(14) 0.38738(7) 0.0498(4) Uani 1 1 d . . . . .
N1 N 0.33107(17) 0.83360(13) 0.95897(7) 0.0341(4) Uani 1 1 d . . . . .
N2 N 0.34899(15) 0.71574(12) 0.86651(7) 0.0270(3) Uani 1 1 d . . . . .
C1 C 0.22685(19) 0.87314(15) 0.90355(9) 0.0300(4) Uani 1 1 d . . . . .
C2 C 0.23733(18) 0.80100(14) 0.84512(8) 0.0273(4) Uani 1 1 d . . . . .
C3 C 0.14601(19) 0.82109(15) 0.78106(9) 0.0312(4) Uani 1 1 d . . . . .
H3 H 0.1545 0.7735 0.7416 0.037 Uiso 1 1 calc R U . . .
C4 C 0.0437(2) 0.91422(16) 0.77934(9) 0.0342(4) Uani 1 1 d . . . . .
C5 C 0.0302(2) 0.98546(15) 0.83722(10) 0.0356(4) Uani 1 1 d . . . . .
C6 C 0.1210(2) 0.96845(15) 0.89937(10) 0.0353(4) Uani 1 1 d . . . . .
H6 H 0.1130 1.0187 0.9380 0.042 Uiso 1 1 calc R U . . .
C7 C 0.4002(2) 0.74028(15) 0.93506(8) 0.0307(4) Uani 1 1 d . . . . .
C8 C 0.5224(2) 0.67589(17) 0.98048(9) 0.0376(5) Uani 1 1 d . . . . .
H8 H 0.5471 0.7047 1.0266 0.045 Uiso 1 1 calc R U . . .
C9 C 0.39347(19) 0.61722(15) 0.82277(8) 0.0281(4) Uani 1 1 d . . . . .
H9A H 0.4901 0.5823 0.8461 0.034 Uiso 1 1 calc R U . . .
H9B H 0.4066 0.6544 0.7800 0.034 Uiso 1 1 calc R U . . .
C10 C 0.27919(19) 0.51249(15) 0.80614(8) 0.0271(4) Uani 1 1 d . . . . .
C11 C 0.2038(2) 0.48611(15) 0.73844(9) 0.0318(4) Uani 1 1 d . . . . .
C12 C 0.1001(2) 0.38717(18) 0.72527(11) 0.0450(5) Uani 1 1 d . . . . .
H12 H 0.0474 0.3695 0.6799 0.054 Uiso 1 1 calc R U . . .
C13 C 0.0738(2) 0.31560(18) 0.77688(12) 0.0510(6) Uani 1 1 d . . . . .
H13 H 0.0037 0.2485 0.7671 0.061 Uiso 1 1 calc R U . . .
C14 C 0.1495(2) 0.34109(17) 0.84358(11) 0.0440(5) Uani 1 1 d . . . . .
H14 H 0.1316 0.2912 0.8793 0.053 Uiso 1 1 calc R U . . .
C15 C 0.2508(2) 0.43911(16) 0.85772(9) 0.0333(4) Uani 1 1 d . . . . .
H15 H 0.3017 0.4565 0.9034 0.040 Uiso 1 1 calc R U . . .
C16 C 0.2272(2) 0.55693(17) 0.68230(9) 0.0346(4) Uani 1 1 d . . . . .
C17 C 0.2396(2) 0.61367(17) 0.63287(9) 0.0357(4) Uani 1 1 d . . . . .
C18 C 0.2474(2) 0.67549(17) 0.57150(8) 0.0330(4) Uani 1 1 d . . . . .
C19 C 0.2933(2) 0.79982(17) 0.57117(9) 0.0392(5) Uani 1 1 d . . . . .
H19 H 0.3218 0.8456 0.6131 0.047 Uiso 1 1 calc R U . . .
C20 C 0.2982(2) 0.85832(18) 0.51129(9) 0.0391(5) Uani 1 1 d . . . . .
H20 H 0.3284 0.9436 0.5121 0.047 Uiso 1 1 calc R U . . .
C21 C 0.2582(2) 0.79021(18) 0.44943(9) 0.0364(4) Uani 1 1 d . . . . .
C22 C 0.2127(2) 0.66638(18) 0.44909(9) 0.0382(5) Uani 1 1 d . . . . .
H22 H 0.1857 0.6204 0.4072 0.046 Uiso 1 1 calc R U . . .
C23 C 0.2062(2) 0.60932(18) 0.50853(9) 0.0371(4) Uani 1 1 d . . . . .
H23 H 0.1737 0.5246 0.5073 0.044 Uiso 1 1 calc R U . . .
C24 C 0.3245(3) 0.9594(2) 0.38548(12) 0.0641(7) Uani 1 1 d . . . . .
H24A H 0.3279 0.9781 0.3385 0.096 Uiso 1 1 calc R U . . .
H24B H 0.4254 0.9625 0.4140 0.096 Uiso 1 1 calc R U . . .
H24C H 0.2627 1.0216 0.4026 0.096 Uiso 1 1 calc R U . . .
F3 F 0.42410(12) 1.07992(9) 0.83524(6) 0.0430(3) Uani 1 1 d . . . . .
F4 F 0.44652(12) 0.94997(10) 0.72449(5) 0.0451(3) Uani 1 1 d . . . . .
O3 O 1.09302(15) 0.59117(13) 0.96474(7) 0.0471(4) Uani 1 1 d . . . . .
O4 O 0.74328(16) 0.84679(14) 0.38842(7) 0.0529(4) Uani 1 1 d . . . . .
N3 N 0.83256(17) 0.83542(13) 0.96152(7) 0.0335(4) Uani 1 1 d . . . . .
N4 N 0.84752(15) 0.71948(12) 0.86791(7) 0.0270(3) Uani 1 1 d . . . . .
C25 C 0.7273(2) 0.87652(15) 0.90671(8) 0.0294(4) Uani 1 1 d . . . . .
C26 C 0.73575(18) 0.80554(14) 0.84740(8) 0.0271(4) Uani 1 1 d . . . . .
C27 C 0.64331(19) 0.82786(15) 0.78386(9) 0.0294(4) Uani 1 1 d . . . . .
H27 H 0.6502 0.7812 0.7439 0.035 Uiso 1 1 calc R U . . .
C28 C 0.5424(2) 0.92170(16) 0.78341(9) 0.0317(4) Uani 1 1 d . . . . .
C29 C 0.5311(2) 0.99165(15) 0.84229(10) 0.0326(4) Uani 1 1 d . . . . .
C30 C 0.6230(2) 0.97235(15) 0.90403(9) 0.0328(4) Uani 1 1 d . . . . .
H30 H 0.6165 1.0215 0.9432 0.039 Uiso 1 1 calc R U . . .
C31 C 0.9007(2) 0.74234(15) 0.93644(8) 0.0308(4) Uani 1 1 d . . . . .
C32 C 1.0225(2) 0.67688(17) 0.98093(9) 0.0371(4) Uani 1 1 d . . . . .
H32 H 1.0483 0.7049 1.0272 0.045 Uiso 1 1 calc R U . . .
C33 C 0.89147(19) 0.62131(15) 0.82345(8) 0.0283(4) Uani 1 1 d . . . . .
H33A H 0.9888 0.5868 0.8462 0.034 Uiso 1 1 calc R U . . .
H33B H 0.9032 0.6591 0.7806 0.034 Uiso 1 1 calc R U . . .
C34 C 0.77843(19) 0.51618(15) 0.80707(8) 0.0271(4) Uani 1 1 d . . . . .
C35 C 0.6981(2) 0.49307(16) 0.73999(9) 0.0316(4) Uani 1 1 d . . . . .
C36 C 0.5925(2) 0.39535(18) 0.72692(11) 0.0458(5) Uani 1 1 d . . . . .
H36 H 0.5354 0.3809 0.6820 0.055 Uiso 1 1 calc R U . . .
C37 C 0.5710(2) 0.32027(18) 0.77845(12) 0.0493(5) Uani 1 1 d . . . . .
H37 H 0.5004 0.2536 0.7689 0.059 Uiso 1 1 calc R U . . .
C38 C 0.6524(2) 0.34208(17) 0.84448(11) 0.0435(5) Uani 1 1 d . . . . .
H38 H 0.6382 0.2898 0.8800 0.052 Uiso 1 1 calc R U . . .
C39 C 0.7544(2) 0.44000(16) 0.85855(9) 0.0341(4) Uani 1 1 d . . . . .
H39 H 0.8085 0.4553 0.9039 0.041 Uiso 1 1 calc R U . . .
C40 C 0.7194(2) 0.56664(17) 0.68436(9) 0.0347(4) Uani 1 1 d . . . . .
C41 C 0.7337(2) 0.62309(17) 0.63525(9) 0.0352(4) Uani 1 1 d . . . . .
C42 C 0.7418(2) 0.68397(16) 0.57357(9) 0.0325(4) Uani 1 1 d . . . . .
C43 C 0.8707(2) 0.74260(18) 0.56454(9) 0.0388(5) Uani 1 1 d . . . . .
H43 H 0.9561 0.7449 0.6009 0.047 Uiso 1 1 calc R U . . .
C44 C 0.8775(2) 0.79780(18) 0.50377(9) 0.0408(5) Uani 1 1 d . . . . .
H44 H 0.9665 0.8375 0.4987 0.049 Uiso 1 1 calc R U . . .
C45 C 0.7525(2) 0.79448(18) 0.45017(9) 0.0386(5) Uani 1 1 d . . . . .
C46 C 0.6242(2) 0.73551(18) 0.45843(9) 0.0409(5) Uani 1 1 d . . . . .
H46 H 0.5391 0.7326 0.4219 0.049 Uiso 1 1 calc R U . . .
C47 C 0.6183(2) 0.68110(17) 0.51870(9) 0.0378(5) Uani 1 1 d . . . . .
H47 H 0.5292 0.6409 0.5233 0.045 Uiso 1 1 calc R U . . .
C48 C 0.8718(3) 0.9058(2) 0.37545(11) 0.0562(6) Uani 1 1 d . . . . .
H48A H 0.8495 0.9375 0.3292 0.084 Uiso 1 1 calc R U . . .
H48B H 0.9526 0.8449 0.3801 0.084 Uiso 1 1 calc R U . . .
H48C H 0.9021 0.9756 0.4081 0.084 Uiso 1 1 calc R U . . .


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

# MOLECULAR GEOMETRY

_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 C5 1.355(2) . ?
F2 C4 1.355(2) . ?
O1 C8 1.202(2) . ?
O2 C21 1.369(2) . ?
O2 C24 1.428(3) . ?
N1 C7 1.321(2) . ?
N1 C1 1.380(2) . ?
N2 C7 1.377(2) . ?
N2 C2 1.379(2) . ?
N2 C9 1.471(2) . ?
C1 C6 1.402(2) . ?
C1 C2 1.412(2) . ?
C2 C3 1.400(2) . ?
C3 C4 1.368(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.405(3) . ?
C5 C6 1.362(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.470(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.514(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C15 1.388(2) . ?
C10 C11 1.410(2) . ?
C11 C12 1.403(3) . ?
C11 C16 1.433(3) . ?
C12 C13 1.371(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.207(3) . ?
C17 C18 1.434(3) . ?
C18 C19 1.392(3) . ?
C18 C23 1.412(2) . ?
C19 C20 1.384(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.403(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.385(3) . ?
C22 C23 1.372(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
F3 C29 1.3530(19) . ?
F4 C28 1.3567(19) . ?
O3 C32 1.203(2) . ?
O4 C45 1.364(2) . ?
O4 C48 1.419(3) . ?
N3 C31 1.324(2) . ?
N3 C25 1.382(2) . ?
N4 C31 1.376(2) . ?
N4 C26 1.383(2) . ?
N4 C33 1.476(2) . ?
C25 C30 1.399(2) . ?
C25 C26 1.415(2) . ?
C26 C27 1.400(2) . ?
C27 C28 1.367(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.409(2) . ?
C29 C30 1.364(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.465(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.509(2) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C39 1.391(2) . ?
C34 C35 1.407(2) . ?
C35 C36 1.405(3) . ?
C35 C40 1.434(3) . ?
C36 C37 1.377(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.390(3) . ?
C37 H37 0.9500 . ?
C38 C39 1.385(3) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C40 C41 1.204(3) . ?
C41 C42 1.435(3) . ?
C42 C43 1.392(3) . ?
C42 C47 1.402(2) . ?
C43 C44 1.388(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.395(3) . ?
C44 H44 0.9500 . ?
C45 C46 1.384(3) . ?
C46 C47 1.373(3) . ?
C46 H46 0.9500 . ?
C47 H47 0.9500 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 O2 C24 118.25(16) . . ?
C7 N1 C1 104.81(14) . . ?
C7 N2 C2 105.78(13) . . ?
C7 N2 C9 129.52(14) . . ?
C2 N2 C9 124.64(14) . . ?
N1 C1 C6 129.73(16) . . ?
N1 C1 C2 109.87(15) . . ?
C6 C1 C2 120.40(16) . . ?
N2 C2 C3 131.58(15) . . ?
N2 C2 C1 105.86(14) . . ?
C3 C2 C1 122.56(16) . . ?
C4 C3 C2 115.14(16) . . ?
C4 C3 H3 122.4 . . ?
C2 C3 H3 122.4 . . ?
F2 C4 C3 119.51(16) . . ?
F2 C4 C5 117.49(16) . . ?
C3 C4 C5 122.99(17) . . ?
F1 C5 C6 120.49(17) . . ?
F1 C5 C4 117.33(17) . . ?
C6 C5 C4 122.17(16) . . ?
C5 C6 C1 116.71(16) . . ?
C5 C6 H6 121.6 . . ?
C1 C6 H6 121.6 . . ?
N1 C7 N2 113.66(15) . . ?
N1 C7 C8 120.00(15) . . ?
N2 C7 C8 126.32(15) . . ?
O1 C8 C7 126.41(16) . . ?
O1 C8 H8 116.8 . . ?
C7 C8 H8 116.8 . . ?
N2 C9 C10 111.76(14) . . ?
N2 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N2 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C15 C10 C11 119.35(16) . . ?
C15 C10 C9 119.87(15) . . ?
C11 C10 C9 120.75(16) . . ?
C12 C11 C10 118.83(17) . . ?
C12 C11 C16 118.35(17) . . ?
C10 C11 C16 122.82(16) . . ?
C13 C12 C11 120.97(18) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 120.06(19) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 119.86(19) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C10 120.92(17) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C17 C16 C11 176.3(2) . . ?
C16 C17 C18 176.3(2) . . ?
C19 C18 C23 118.05(17) . . ?
C19 C18 C17 122.51(15) . . ?
C23 C18 C17 119.43(17) . . ?
C20 C19 C18 121.64(16) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C21 119.25(18) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
O2 C21 C22 115.93(16) . . ?
O2 C21 C20 124.40(18) . . ?
C22 C21 C20 119.67(18) . . ?
C23 C22 C21 120.83(16) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C18 120.55(18) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C45 O4 C48 118.41(17) . . ?
C31 N3 C25 104.79(13) . . ?
C31 N4 C26 106.03(13) . . ?
C31 N4 C33 128.99(14) . . ?
C26 N4 C33 124.93(14) . . ?
N3 C25 C30 129.46(15) . . ?
N3 C25 C26 109.94(15) . . ?
C30 C25 C26 120.59(16) . . ?
N4 C26 C27 131.93(15) . . ?
N4 C26 C25 105.62(14) . . ?
C27 C26 C25 122.45(15) . . ?
C28 C27 C26 115.20(15) . . ?
C28 C27 H27 122.4 . . ?
C26 C27 H27 122.4 . . ?
F4 C28 C27 119.87(15) . . ?
F4 C28 C29 117.22(15) . . ?
C27 C28 C29 122.91(16) . . ?
F3 C29 C30 120.75(16) . . ?
F3 C29 C28 117.04(16) . . ?
C30 C29 C28 122.20(16) . . ?
C29 C30 C25 116.61(15) . . ?
C29 C30 H30 121.7 . . ?
C25 C30 H30 121.7 . . ?
N3 C31 N4 113.62(15) . . ?
N3 C31 C32 119.79(15) . . ?
N4 C31 C32 126.58(15) . . ?
O3 C32 C31 126.47(17) . . ?
O3 C32 H32 116.8 . . ?
C31 C32 H32 116.8 . . ?
N4 C33 C34 111.99(14) . . ?
N4 C33 H33A 109.2 . . ?
C34 C33 H33A 109.2 . . ?
N4 C33 H33B 109.2 . . ?
C34 C33 H33B 109.2 . . ?
H33A C33 H33B 107.9 . . ?
C39 C34 C35 119.40(16) . . ?
C39 C34 C33 119.84(15) . . ?
C35 C34 C33 120.75(16) . . ?
C36 C35 C34 119.06(17) . . ?
C36 C35 C40 118.71(17) . . ?
C34 C35 C40 122.23(16) . . ?
C37 C36 C35 120.73(19) . . ?
C37 C36 H36 119.6 . . ?
C35 C36 H36 119.6 . . ?
C36 C37 C38 120.00(19) . . ?
C36 C37 H37 120.0 . . ?
C38 C37 H37 120.0 . . ?
C39 C38 C37 120.01(19) . . ?
C39 C38 H38 120.0 . . ?
C37 C38 H38 120.0 . . ?
C38 C39 C34 120.77(18) . . ?
C38 C39 H39 119.6 . . ?
C34 C39 H39 119.6 . . ?
C41 C40 C35 176.37(18) . . ?
C40 C41 C42 175.5(2) . . ?
C43 C42 C47 117.73(17) . . ?
C43 C42 C41 122.52(17) . . ?
C47 C42 C41 119.70(18) . . ?
C44 C43 C42 121.61(18) . . ?
C44 C43 H43 119.2 . . ?
C42 C43 H43 119.2 . . ?
C43 C44 C45 119.46(19) . . ?
C43 C44 H44 120.3 . . ?
C45 C44 H44 120.3 . . ?
O4 C45 C46 115.17(17) . . ?
O4 C45 C44 125.5(2) . . ?
C46 C45 C44 119.37(18) . . ?
C47 C46 C45 120.85(18) . . ?
C47 C46 H46 119.6 . . ?
C45 C46 H46 119.6 . . ?
C46 C47 C42 120.97(19) . . ?
C46 C47 H47 119.5 . . ?
C42 C47 H47 119.5 . . ?
O4 C48 H48A 109.5 . . ?
O4 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
O4 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 C1 C6 179.10(18) . . . . ?
C7 N1 C1 C2 -0.8(2) . . . . ?
C7 N2 C2 C3 179.68(18) . . . . ?
C9 N2 C2 C3 -2.9(3) . . . . ?
C7 N2 C2 C1 -0.41(18) . . . . ?
C9 N2 C2 C1 177.00(15) . . . . ?
N1 C1 C2 N2 0.7(2) . . . . ?
C6 C1 C2 N2 -179.14(15) . . . . ?
N1 C1 C2 C3 -179.33(16) . . . . ?
C6 C1 C2 C3 0.8(3) . . . . ?
N2 C2 C3 C4 178.69(17) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C2 C3 C4 F2 -178.63(15) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
F2 C4 C5 F1 0.1(2) . . . . ?
C3 C4 C5 F1 -178.67(16) . . . . ?
F2 C4 C5 C6 -179.74(16) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
F1 C5 C6 C1 178.28(15) . . . . ?
C4 C5 C6 C1 -1.9(3) . . . . ?
N1 C1 C6 C5 -179.08(18) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
C1 N1 C7 N2 0.5(2) . . . . ?
C1 N1 C7 C8 178.90(16) . . . . ?
C2 N2 C7 N1 -0.1(2) . . . . ?
C9 N2 C7 N1 -177.31(16) . . . . ?
C2 N2 C7 C8 -178.32(18) . . . . ?
C9 N2 C7 C8 4.4(3) . . . . ?
N1 C7 C8 O1 -179.80(19) . . . . ?
N2 C7 C8 O1 -1.6(3) . . . . ?
C7 N2 C9 C10 103.99(19) . . . . ?
C2 N2 C9 C10 -72.8(2) . . . . ?
N2 C9 C10 C15 -64.3(2) . . . . ?
N2 C9 C10 C11 117.51(17) . . . . ?
C15 C10 C11 C12 1.0(2) . . . . ?
C9 C10 C11 C12 179.20(16) . . . . ?
C15 C10 C11 C16 -179.72(16) . . . . ?
C9 C10 C11 C16 -1.5(2) . . . . ?
C10 C11 C12 C13 -1.1(3) . . . . ?
C16 C11 C12 C13 179.56(18) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C14 C15 C10 -0.4(3) . . . . ?
C11 C10 C15 C14 -0.2(3) . . . . ?
C9 C10 C15 C14 -178.48(16) . . . . ?
C23 C18 C19 C20 0.3(3) . . . . ?
C17 C18 C19 C20 -179.14(18) . . . . ?
C18 C19 C20 C21 -1.0(3) . . . . ?
C24 O2 C21 C22 -172.96(18) . . . . ?
C24 O2 C21 C20 6.2(3) . . . . ?
C19 C20 C21 O2 -178.30(17) . . . . ?
C19 C20 C21 C22 0.8(3) . . . . ?
O2 C21 C22 C23 179.20(16) . . . . ?
C20 C21 C22 C23 0.0(3) . . . . ?
C21 C22 C23 C18 -0.7(3) . . . . ?
C19 C18 C23 C22 0.6(3) . . . . ?
C17 C18 C23 C22 -179.99(17) . . . . ?
C31 N3 C25 C30 179.42(18) . . . . ?
C31 N3 C25 C26 -0.7(2) . . . . ?
C31 N4 C26 C27 179.35(18) . . . . ?
C33 N4 C26 C27 -3.1(3) . . . . ?
C31 N4 C26 C25 -0.47(18) . . . . ?
C33 N4 C26 C25 177.13(15) . . . . ?
N3 C25 C26 N4 0.72(19) . . . . ?
C30 C25 C26 N4 -179.36(15) . . . . ?
N3 C25 C26 C27 -179.11(16) . . . . ?
C30 C25 C26 C27 0.8(3) . . . . ?
N4 C26 C27 C28 179.08(17) . . . . ?
C25 C26 C27 C28 -1.1(3) . . . . ?
C26 C27 C28 F4 -179.35(15) . . . . ?
C26 C27 C28 C29 0.0(3) . . . . ?
F4 C28 C29 F3 1.0(2) . . . . ?
C27 C28 C29 F3 -178.45(16) . . . . ?
F4 C28 C29 C30 -179.12(16) . . . . ?
C27 C28 C29 C30 1.5(3) . . . . ?
F3 C29 C30 C25 178.15(15) . . . . ?
C28 C29 C30 C25 -1.8(3) . . . . ?
N3 C25 C30 C29 -179.43(18) . . . . ?
C26 C25 C30 C29 0.7(3) . . . . ?
C25 N3 C31 N4 0.4(2) . . . . ?
C25 N3 C31 C32 179.10(16) . . . . ?
C26 N4 C31 N3 0.1(2) . . . . ?
C33 N4 C31 N3 -177.40(16) . . . . ?
C26 N4 C31 C32 -178.56(18) . . . . ?
C33 N4 C31 C32 4.0(3) . . . . ?
N3 C31 C32 O3 179.83(19) . . . . ?
N4 C31 C32 O3 -1.6(3) . . . . ?
C31 N4 C33 C34 103.66(19) . . . . ?
C26 N4 C33 C34 -73.4(2) . . . . ?
N4 C33 C34 C39 -65.7(2) . . . . ?
N4 C33 C34 C35 115.15(17) . . . . ?
C39 C34 C35 C36 1.6(2) . . . . ?
C33 C34 C35 C36 -179.21(16) . . . . ?
C39 C34 C35 C40 -178.87(16) . . . . ?
C33 C34 C35 C40 0.3(2) . . . . ?
C34 C35 C36 C37 -2.1(3) . . . . ?
C40 C35 C36 C37 178.36(18) . . . . ?
C35 C36 C37 C38 1.0(3) . . . . ?
C36 C37 C38 C39 0.6(3) . . . . ?
C37 C38 C39 C34 -1.0(3) . . . . ?
C35 C34 C39 C38 -0.1(3) . . . . ?
C33 C34 C39 C38 -179.23(16) . . . . ?
C47 C42 C43 C44 0.7(3) . . . . ?
C41 C42 C43 C44 178.11(16) . . . . ?
C42 C43 C44 C45 -0.2(3) . . . . ?
C48 O4 C45 C46 -178.18(17) . . . . ?
C48 O4 C45 C44 2.6(3) . . . . ?
C43 C44 C45 O4 178.76(17) . . . . ?
C43 C44 C45 C46 -0.4(3) . . . . ?
O4 C45 C46 C47 -178.84(16) . . . . ?
C44 C45 C46 C47 0.4(3) . . . . ?
C45 C46 C47 C42 0.1(3) . . . . ?
C43 C42 C47 C46 -0.7(3) . . . . ?
C41 C42 C47 C46 -178.18(16) . . . . ?

_refine_diff_density_max         0.235
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.042

