# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

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

data_4d
_database_code_depnum_ccdc_archive 'CCDC 1442704'
_audit_update_record             
;
2015-12-15 deposited with the CCDC.
2016-01-08 downloaded from the CCDC.
;


#-----------------------------------------------------
#------------------ COMPOUND 1    ---------------------
#-----------------------------------------------------


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H20 N2 O'
_chemical_formula_sum            'C29 H20 N2 O'
_chemical_formula_weight         412.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.0687(6)
_cell_length_b                   10.7492(7)
_cell_length_c                   12.4376(13)
_cell_angle_alpha                114.884(8)
_cell_angle_beta                 102.785(7)
_cell_angle_gamma                95.489(5)
_cell_volume                     1047.90(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4768
_cell_measurement_theta_min      4.0800
_cell_measurement_theta_max      73.5987

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.028
_exptl_absorpt_coefficient_mu    0.624
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.59398
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Nova (Cu) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 8.2640
_diffrn_reflns_number            7818
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.094
_diffrn_reflns_theta_max         73.683
_diffrn_reflns_theta_full        67.680
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             3953
_reflns_number_gt                3175
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1096P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3953
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1468
_refine_ls_wR_factor_gt          0.1398
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
H13 H 0.694(2) 0.316(2) 0.4350(19) 0.024(4) Uiso 1 1 d . . . . .
H14 H 0.495(2) 0.460(2) 0.3337(18) 0.024(5) Uiso 1 1 d . . . . .
C1 C 0.75444(19) 0.52634(15) 0.50756(15) 0.0249(3) Uani 1 1 d . . . . .
C2 C 0.73091(19) 0.66078(15) 0.50371(15) 0.0253(3) Uani 1 1 d . . . . .
C3 C 0.87387(19) 0.76724(15) 0.58773(15) 0.0257(3) Uani 1 1 d . . . . .
C4 C 0.9091(2) 0.90672(16) 0.61078(17) 0.0305(4) Uani 1 1 d . . . . .
H4 H 0.8398 0.9441 0.5721 0.037 Uiso 1 1 calc R U . . .
C5 C 1.0513(2) 0.98794(17) 0.69369(18) 0.0332(4) Uani 1 1 d . . . . .
H5 H 1.0788 1.0812 0.7104 0.040 Uiso 1 1 calc R U . . .
C6 C 1.15329(19) 0.93093(17) 0.75210(16) 0.0304(4) Uani 1 1 d . . . . .
H6 H 1.2477 0.9874 0.8078 0.036 Uiso 1 1 calc R U . . .
C7 C 1.11717(19) 0.79101(16) 0.72907(16) 0.0273(3) Uani 1 1 d . . . . .
H7 H 1.1860 0.7540 0.7685 0.033 Uiso 1 1 calc R U . . .
C8 C 0.97466(19) 0.70820(15) 0.64504(15) 0.0250(3) Uani 1 1 d . . . . .
C9 C 0.90018(19) 0.55957(15) 0.60227(15) 0.0249(3) Uani 1 1 d . . . . .
C10 C 0.95821(19) 0.47318(16) 0.64824(15) 0.0270(4) Uani 1 1 d . . . . .
C11 C 0.8782(2) 0.33179(17) 0.60928(16) 0.0310(4) Uani 1 1 d . . . . .
C12 C 1.1026(2) 0.51374(16) 0.74274(16) 0.0292(4) Uani 1 1 d . . . . .
C13 C 0.66038(19) 0.39661(15) 0.42696(15) 0.0250(3) Uani 1 1 d . . . . .
C14 C 0.52417(19) 0.37542(16) 0.33389(15) 0.0259(3) Uani 1 1 d . . . . .
C15 C 0.42956(18) 0.24971(15) 0.24504(15) 0.0241(3) Uani 1 1 d . . . . .
C16 C 0.44641(17) 0.10927(15) 0.23336(15) 0.0232(3) Uani 1 1 d . . . . .
C17 C 0.41721(17) -0.00163(16) 0.11453(15) 0.0246(3) Uani 1 1 d . . . . .
H17 H 0.3835 0.0140 0.0459 0.030 Uiso 1 1 calc R U . . .
C18 C 0.43762(18) -0.13452(15) 0.09714(16) 0.0263(3) Uani 1 1 d . . . . .
H18 H 0.4198 -0.2060 0.0173 0.032 Uiso 1 1 calc R U . . .
C19 C 0.48453(18) -0.16176(16) 0.19807(16) 0.0267(3) Uani 1 1 d . . . . .
C20 C 0.50945(18) -0.05277(16) 0.31650(16) 0.0272(3) Uani 1 1 d . . . . .
H20 H 0.5391 -0.0698 0.3847 0.033 Uiso 1 1 calc R U . . .
C21 C 0.49079(18) 0.08117(16) 0.33481(15) 0.0257(3) Uani 1 1 d . . . . .
H21 H 0.5078 0.1522 0.4147 0.031 Uiso 1 1 calc R U . . .
C22 C 0.5053(2) -0.30596(17) 0.17964(18) 0.0347(4) Uani 1 1 d . . . . .
H22A H 0.6113 -0.3015 0.2178 0.052 Uiso 1 1 calc R U . . .
H22B H 0.4781 -0.3685 0.0926 0.052 Uiso 1 1 calc R U . . .
H22C H 0.4396 -0.3398 0.2168 0.052 Uiso 1 1 calc R U . . .
C23 C 0.30358(19) 0.25533(15) 0.15018(15) 0.0243(3) Uani 1 1 d . . . . .
C24 C 0.15340(19) 0.17544(15) 0.11269(15) 0.0255(3) Uani 1 1 d . . . . .
H24 H 0.1344 0.1111 0.1424 0.031 Uiso 1 1 calc R U . . .
C25 C 0.03335(18) 0.19101(16) 0.03236(15) 0.0268(3) Uani 1 1 d . . . . .
H25 H -0.0660 0.1395 0.0113 0.032 Uiso 1 1 calc R U . . .
C26 C 0.0583(2) 0.28295(16) -0.01798(15) 0.0276(3) Uani 1 1 d . . . . .
C27 C 0.20918(19) 0.35762(16) 0.01502(16) 0.0285(4) Uani 1 1 d . . . . .
H27 H 0.2292 0.4168 -0.0195 0.034 Uiso 1 1 calc R U . . .
C28 C 0.32955(19) 0.34552(16) 0.09801(16) 0.0273(3) Uani 1 1 d . . . . .
H28 H 0.4286 0.3977 0.1194 0.033 Uiso 1 1 calc R U . . .
C29 C -0.0736(2) 0.30130(19) -0.10293(17) 0.0333(4) Uani 1 1 d . . . . .
H29A H -0.1226 0.2123 -0.1734 0.050 Uiso 1 1 calc R U . . .
H29B H -0.0352 0.3659 -0.1302 0.050 Uiso 1 1 calc R U . . .
H29C H -0.1473 0.3375 -0.0597 0.050 Uiso 1 1 calc R U . . .
N1 N 0.8212(2) 0.21807(17) 0.58250(16) 0.0423(4) Uani 1 1 d . . . . .
N2 N 1.21725(18) 0.54050(16) 0.81764(15) 0.0352(4) Uani 1 1 d . . . . .
O1 O 0.61938(14) 0.68193(11) 0.44330(11) 0.0310(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C13 1.376(2) . ?
C1 C9 1.459(2) . ?
C1 C2 1.500(2) . ?
C2 O1 1.221(2) . ?
C2 C3 1.481(2) . ?
C3 C4 1.392(2) . ?
C3 C8 1.396(2) . ?
C4 C5 1.389(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.398(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.398(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.487(2) . ?
C9 C10 1.369(2) . ?
C10 C12 1.437(2) . ?
C10 C11 1.444(2) . ?
C11 N1 1.154(2) . ?
C12 N2 1.149(3) . ?
C13 C14 1.417(2) . ?
C13 H13 0.99(2) . ?
C14 C15 1.373(2) . ?
C14 H14 0.97(2) . ?
C15 C23 1.476(2) . ?
C15 C16 1.481(2) . ?
C16 C17 1.400(2) . ?
C16 C21 1.402(2) . ?
C17 C18 1.389(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.393(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.394(2) . ?
C19 C22 1.505(2) . ?
C20 C21 1.393(2) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.403(2) . ?
C23 C28 1.403(2) . ?
C24 C25 1.380(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.400(2) . ?
C25 H25 0.9300 . ?
C26 C27 1.396(2) . ?
C26 C29 1.499(2) . ?
C27 C28 1.384(2) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 C1 C9 128.26(15) . . ?
C13 C1 C2 124.55(15) . . ?
C9 C1 C2 106.93(13) . . ?
O1 C2 C3 125.21(14) . . ?
O1 C2 C1 128.51(14) . . ?
C3 C2 C1 106.26(13) . . ?
C4 C3 C8 122.65(15) . . ?
C4 C3 C2 127.49(15) . . ?
C8 C3 C2 109.86(13) . . ?
C5 C4 C3 117.54(16) . . ?
C5 C4 H4 121.2 . . ?
C3 C4 H4 121.2 . . ?
C4 C5 C6 120.62(15) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C7 121.62(15) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C8 118.14(15) . . ?
C6 C7 H7 120.9 . . ?
C8 C7 H7 120.9 . . ?
C3 C8 C7 119.42(14) . . ?
C3 C8 C9 108.75(14) . . ?
C7 C8 C9 131.81(15) . . ?
C10 C9 C1 127.18(14) . . ?
C10 C9 C8 125.04(16) . . ?
C1 C9 C8 107.75(14) . . ?
C9 C10 C12 124.09(14) . . ?
C9 C10 C11 123.43(15) . . ?
C12 C10 C11 112.45(14) . . ?
N1 C11 C10 176.17(19) . . ?
N2 C12 C10 177.13(17) . . ?
C1 C13 C14 123.63(15) . . ?
C1 C13 H13 116.3(12) . . ?
C14 C13 H13 120.1(12) . . ?
C15 C14 C13 127.42(15) . . ?
C15 C14 H14 116.8(12) . . ?
C13 C14 H14 115.8(12) . . ?
C14 C15 C23 116.80(14) . . ?
C14 C15 C16 125.84(15) . . ?
C23 C15 C16 117.32(13) . . ?
C17 C16 C21 118.05(14) . . ?
C17 C16 C15 118.31(14) . . ?
C21 C16 C15 123.64(14) . . ?
C18 C17 C16 121.27(15) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 120.63(15) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C20 118.35(14) . . ?
C18 C19 C22 120.83(15) . . ?
C20 C19 C22 120.81(15) . . ?
C21 C20 C19 121.37(15) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C16 120.27(15) . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C28 117.87(15) . . ?
C24 C23 C15 121.46(14) . . ?
C28 C23 C15 120.62(14) . . ?
C25 C24 C23 120.94(14) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C24 C25 C26 121.23(14) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C27 C26 C25 117.73(15) . . ?
C27 C26 C29 121.53(15) . . ?
C25 C26 C29 120.73(15) . . ?
C28 C27 C26 121.45(15) . . ?
C28 C27 H27 119.3 . . ?
C26 C27 H27 119.3 . . ?
C27 C28 C23 120.67(15) . . ?
C27 C28 H28 119.7 . . ?
C23 C28 H28 119.7 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
C13 C1 C2 O1 10.5(3) . . . . ?
C9 C1 C2 O1 -174.94(16) . . . . ?
C13 C1 C2 C3 -168.37(15) . . . . ?
C9 C1 C2 C3 6.15(17) . . . . ?
O1 C2 C3 C4 -1.8(3) . . . . ?
C1 C2 C3 C4 177.19(16) . . . . ?
O1 C2 C3 C8 177.84(16) . . . . ?
C1 C2 C3 C8 -3.21(18) . . . . ?
C8 C3 C4 C5 0.5(3) . . . . ?
C2 C3 C4 C5 -179.91(16) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C4 C3 C8 C7 -0.1(2) . . . . ?
C2 C3 C8 C7 -179.71(14) . . . . ?
C4 C3 C8 C9 178.64(15) . . . . ?
C2 C3 C8 C9 -0.98(18) . . . . ?
C6 C7 C8 C3 -0.2(2) . . . . ?
C6 C7 C8 C9 -178.57(16) . . . . ?
C13 C1 C9 C10 -14.6(3) . . . . ?
C2 C1 C9 C10 171.17(16) . . . . ?
C13 C1 C9 C8 167.47(16) . . . . ?
C2 C1 C9 C8 -6.79(17) . . . . ?
C3 C8 C9 C10 -173.08(16) . . . . ?
C7 C8 C9 C10 5.4(3) . . . . ?
C3 C8 C9 C1 4.94(17) . . . . ?
C7 C8 C9 C1 -176.55(16) . . . . ?
C1 C9 C10 C12 -179.39(16) . . . . ?
C8 C9 C10 C12 -1.8(3) . . . . ?
C1 C9 C10 C11 -1.3(3) . . . . ?
C8 C9 C10 C11 176.32(15) . . . . ?
C9 C1 C13 C14 -176.78(16) . . . . ?
C2 C1 C13 C14 -3.5(3) . . . . ?
C1 C13 C14 C15 175.50(16) . . . . ?
C13 C14 C15 C23 -173.62(15) . . . . ?
C13 C14 C15 C16 3.9(3) . . . . ?
C14 C15 C16 C17 -140.97(17) . . . . ?
C23 C15 C16 C17 36.5(2) . . . . ?
C14 C15 C16 C21 38.7(2) . . . . ?
C23 C15 C16 C21 -143.78(15) . . . . ?
C21 C16 C17 C18 -2.6(2) . . . . ?
C15 C16 C17 C18 177.05(14) . . . . ?
C16 C17 C18 C19 1.5(2) . . . . ?
C17 C18 C19 C20 0.4(2) . . . . ?
C17 C18 C19 C22 179.38(15) . . . . ?
C18 C19 C20 C21 -1.1(2) . . . . ?
C22 C19 C20 C21 179.95(15) . . . . ?
C19 C20 C21 C16 -0.1(2) . . . . ?
C17 C16 C21 C20 2.0(2) . . . . ?
C15 C16 C21 C20 -177.72(14) . . . . ?
C14 C15 C23 C24 -136.20(16) . . . . ?
C16 C15 C23 C24 46.1(2) . . . . ?
C14 C15 C23 C28 41.3(2) . . . . ?
C16 C15 C23 C28 -136.41(16) . . . . ?
C28 C23 C24 C25 -3.6(2) . . . . ?
C15 C23 C24 C25 174.04(14) . . . . ?
C23 C24 C25 C26 2.4(2) . . . . ?
C24 C25 C26 C27 0.5(2) . . . . ?
C24 C25 C26 C29 -178.65(15) . . . . ?
C25 C26 C27 C28 -2.2(2) . . . . ?
C29 C26 C27 C28 176.91(16) . . . . ?
C26 C27 C28 C23 1.1(3) . . . . ?
C24 C23 C28 C27 1.8(2) . . . . ?
C15 C23 C28 C27 -175.78(14) . . . . ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_5b
_database_code_depnum_ccdc_archive 'CCDC 1442705'
_audit_update_record             
;
2015-12-15 deposited with the CCDC.
2016-01-08 downloaded from the CCDC.
;


#-----------------------------------------------------
#------------------ COMPOUND 2    ---------------------
#-----------------------------------------------------

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H14 F2 N4'
_chemical_formula_sum            'C30 H14 F2 N4'
_chemical_formula_weight         468.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   5.4077(2)
_cell_length_b                   9.7318(3)
_cell_length_c                   22.3871(6)
_cell_angle_alpha                89.248(2)
_cell_angle_beta                 89.554(3)
_cell_angle_gamma                80.152(3)
_cell_volume                     1160.68(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(3)
_cell_measurement_reflns_used    9211
_cell_measurement_theta_min      3.9420
_cell_measurement_theta_max      73.7600

_exptl_crystal_description       Needle
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.314
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.045
_exptl_absorpt_coefficient_mu    0.757
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.620
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(3)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13086
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.950
_diffrn_reflns_theta_max         74.375
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4584
_reflns_number_gt                4113
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0744P)²+0.1323P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4584
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1248
_refine_ls_wR_factor_gt          0.1175
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C17 C -0.0050(2) 0.96788(12) 0.27177(5) 0.0461(3) Uani 1 1 d . . . . .
H16 H -0.048(3) 0.7624(16) 0.2832(6) 0.052(4) Uiso 1 1 d . . . . .
H17 H 0.066(3) 1.0288(16) 0.2436(7) 0.051(4) Uiso 1 1 d . . . . .
H20 H 0.021(3) 0.9670(19) 0.4420(8) 0.067(5) Uiso 1 1 d . . . . .
H24 H -0.457(3) 0.8812(16) 0.3130(7) 0.059(4) Uiso 1 1 d . . . . .
H30 H -0.333(3) 1.2014(17) 0.4039(7) 0.064(4) Uiso 1 1 d . . . . .
H26 H 0.295(3) 1.1567(17) 0.2928(7) 0.062(4) Uiso 1 1 d . . . . .
H4 H 0.427(3) 0.4023(18) 0.1291(7) 0.061(4) Uiso 1 1 d . . . . .
H27 H 0.363(4) 1.380(2) 0.3169(9) 0.082(5) Uiso 1 1 d . . . . .
H23 H -0.631(4) 0.736(2) 0.3814(8) 0.074(5) Uiso 1 1 d . . . . .
H7 H 0.508(4) 0.854(2) 0.0545(8) 0.078(5) Uiso 1 1 d . . . . .
H6 H 0.776(4) 0.658(2) 0.0187(9) 0.091(6) Uiso 1 1 d . . . . .
H21 H -0.160(4) 0.824(2) 0.5108(9) 0.090(6) Uiso 1 1 d . . . . .
H5 H 0.741(4) 0.432(2) 0.0546(9) 0.085(6) Uiso 1 1 d . . . . .
H29 H -0.253(4) 1.423(2) 0.4286(9) 0.077(5) Uiso 1 1 d . . . . .
F2 F 0.0893(2) 1.54945(10) 0.38944(6) 0.0939(4) Uani 1 1 d . . . . .
C2 C 0.0976(2) 0.62869(12) 0.18273(5) 0.0441(3) Uani 1 1 d . . . . .
C19 C -0.1976(2) 0.93569(11) 0.37074(5) 0.0432(3) Uani 1 1 d . . . . .
C18 C -0.0719(2) 1.01733(12) 0.32717(5) 0.0432(3) Uani 1 1 d . . . . .
C1 C 0.0417(2) 0.77778(12) 0.19692(5) 0.0442(3) Uani 1 1 d . . . . .
C16 C -0.0125(2) 0.82906(12) 0.25258(5) 0.0451(3) Uani 1 1 d . . . . .
C30 C -0.1808(3) 1.23656(13) 0.38573(6) 0.0500(3) Uani 1 1 d . . . . .
C3 C 0.2924(3) 0.61380(13) 0.13624(5) 0.0484(3) Uani 1 1 d . . . . .
C25 C -0.0230(2) 1.15601(12) 0.34503(5) 0.0441(3) Uani 1 1 d . . . . .
C20 C -0.1147(3) 0.91988(14) 0.42977(6) 0.0530(3) Uani 1 1 d . . . . .
F1 F -0.5074(3) 0.68689(13) 0.48903(5) 0.1081(5) Uani 1 1 d . . . . .
C26 C 0.1777(3) 1.21210(13) 0.32057(6) 0.0523(3) Uani 1 1 d . . . . .
N1 N -0.4172(3) 0.58367(15) 0.27338(6) 0.0686(3) Uani 1 1 d . . . . .
C11 C -0.2404(3) 0.56148(13) 0.24390(6) 0.0517(3) Uani 1 1 d . . . . .
C29 C -0.1439(3) 1.36927(14) 0.40084(7) 0.0591(3) Uani 1 1 d . . . . .
C13 C 0.0127(3) 0.97794(13) 0.12427(6) 0.0539(3) Uani 1 1 d . . . . .
C9 C 0.1248(3) 0.85014(12) 0.14437(5) 0.0472(3) Uani 1 1 d . . . . .
C24 C -0.3937(2) 0.86884(13) 0.35366(6) 0.0499(3) Uani 1 1 d . . . . .
C10 C -0.0273(2) 0.52949(12) 0.20512(5) 0.0474(3) Uani 1 1 d . . . . .
C27 C 0.2162(3) 1.34433(15) 0.33565(7) 0.0592(3) Uani 1 1 d . . . . .
C12 C 0.0233(3) 0.38769(13) 0.18642(7) 0.0584(3) Uani 1 1 d . . . . .
C23 C -0.5000(3) 0.78512(16) 0.39329(7) 0.0617(4) Uani 1 1 d . . . . .
C28 C 0.0533(3) 1.41955(13) 0.37532(7) 0.0608(4) Uani 1 1 d . . . . .
C4 C 0.4460(3) 0.49574(15) 0.11410(6) 0.0585(3) Uani 1 1 d . . . . .
C8 C 0.3145(3) 0.74727(13) 0.11420(5) 0.0512(3) Uani 1 1 d . . . . .
C22 C -0.4084(3) 0.77048(16) 0.45025(7) 0.0668(4) Uani 1 1 d . . . . .
C21 C -0.2200(4) 0.83657(16) 0.46977(6) 0.0663(4) Uani 1 1 d . . . . .
N2 N 0.0520(3) 0.27472(14) 0.17163(9) 0.0866(5) Uani 1 1 d . . . . .
C7 C 0.4914(3) 0.76379(17) 0.07050(6) 0.0651(4) Uani 1 1 d . . . . .
C14 C -0.2190(3) 1.04435(15) 0.14999(7) 0.0644(4) Uani 1 1 d . . . . .
C15 C 0.1017(4) 1.04649(17) 0.07356(7) 0.0720(4) Uani 1 1 d . . . . .
C5 C 0.6234(3) 0.51390(19) 0.07116(7) 0.0692(4) Uani 1 1 d . . . . .
C6 C 0.6472(4) 0.6452(2) 0.04987(7) 0.0737(4) Uani 1 1 d . . . . .
N3 N -0.4095(3) 1.0896(2) 0.17042(10) 0.1021(6) Uani 1 1 d . . . . .
N4 N 0.1685(5) 1.1033(2) 0.03348(8) 0.1127(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C17 C18 1.3601(16) . ?
C17 C16 1.4303(16) . ?
C17 H17 0.980(15) . ?
F2 C28 1.3534(14) . ?
C2 C10 1.3582(16) . ?
C2 C3 1.4658(17) . ?
C2 C1 1.4690(15) . ?
C19 C24 1.3940(17) . ?
C19 C20 1.3968(18) . ?
C19 C18 1.4830(16) . ?
C18 C25 1.4794(15) . ?
C1 C16 1.3594(16) . ?
C1 C9 1.4699(15) . ?
C16 H16 0.978(15) . ?
C30 C29 1.3868(17) . ?
C30 C25 1.3967(18) . ?
C30 H30 1.022(17) . ?
C3 C4 1.3920(19) . ?
C3 C8 1.4071(17) . ?
C25 C26 1.4004(18) . ?
C20 C21 1.3838(19) . ?
C20 H20 0.971(18) . ?
F1 C22 1.3512(16) . ?
C26 C27 1.3847(18) . ?
C26 H26 0.983(17) . ?
N1 C11 1.1485(19) . ?
C11 C10 1.4310(19) . ?
C29 C28 1.366(2) . ?
C29 H29 0.95(2) . ?
C13 C9 1.3596(19) . ?
C13 C14 1.429(2) . ?
C13 C15 1.4306(19) . ?
C9 C8 1.4718(18) . ?
C24 C23 1.3837(19) . ?
C24 H24 0.973(16) . ?
C10 C12 1.4278(17) . ?
C27 C28 1.373(2) . ?
C27 H27 1.00(2) . ?
C12 N2 1.1369(19) . ?
C23 C22 1.369(2) . ?
C23 H23 0.96(2) . ?
C4 C5 1.384(2) . ?
C4 H4 0.987(17) . ?
C8 C7 1.3902(18) . ?
C22 C21 1.371(2) . ?
C21 H21 0.98(2) . ?
C7 C6 1.390(2) . ?
C7 H7 0.96(2) . ?
C14 N3 1.143(2) . ?
C15 N4 1.136(2) . ?
C5 C6 1.384(3) . ?
C5 H5 1.00(2) . ?
C6 H6 1.00(2) . ?

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
C18 C17 C16 124.86(11) . . ?
C18 C17 H17 118.2(9) . . ?
C16 C17 H17 116.7(9) . . ?
C10 C2 C3 128.11(11) . . ?
C10 C2 C1 125.27(11) . . ?
C3 C2 C1 106.35(10) . . ?
C24 C19 C20 118.38(11) . . ?
C24 C19 C18 121.31(11) . . ?
C20 C19 C18 120.27(11) . . ?
C17 C18 C25 120.27(10) . . ?
C17 C18 C19 121.39(10) . . ?
C25 C18 C19 118.34(10) . . ?
C16 C1 C2 124.54(10) . . ?
C16 C1 C9 128.08(10) . . ?
C2 C1 C9 105.34(10) . . ?
C1 C16 C17 126.54(11) . . ?
C1 C16 H16 116.5(9) . . ?
C17 C16 H16 116.8(9) . . ?
C29 C30 C25 121.31(12) . . ?
C29 C30 H30 117.6(9) . . ?
C25 C30 H30 121.0(9) . . ?
C4 C3 C8 120.44(12) . . ?
C4 C3 C2 130.88(12) . . ?
C8 C3 C2 108.67(11) . . ?
C30 C25 C26 118.02(11) . . ?
C30 C25 C18 120.70(11) . . ?
C26 C25 C18 121.25(11) . . ?
C21 C20 C19 120.71(13) . . ?
C21 C20 H20 120.6(10) . . ?
C19 C20 H20 118.7(10) . . ?
C27 C26 C25 120.94(13) . . ?
C27 C26 H26 119.2(10) . . ?
C25 C26 H26 119.8(10) . . ?
N1 C11 C10 176.89(14) . . ?
C28 C29 C30 118.32(13) . . ?
C28 C29 H29 121.5(11) . . ?
C30 C29 H29 120.2(12) . . ?
C9 C13 C14 120.23(12) . . ?
C9 C13 C15 123.14(14) . . ?
C14 C13 C15 116.34(14) . . ?
C13 C9 C1 124.64(12) . . ?
C13 C9 C8 128.53(11) . . ?
C1 C9 C8 105.96(10) . . ?
C23 C24 C19 121.34(13) . . ?
C23 C24 H24 119.4(9) . . ?
C19 C24 H24 119.2(9) . . ?
C2 C10 C12 122.82(12) . . ?
C2 C10 C11 122.68(11) . . ?
C12 C10 C11 114.09(11) . . ?
C28 C27 C26 118.54(13) . . ?
C28 C27 H27 123.7(11) . . ?
C26 C27 H27 117.8(11) . . ?
N2 C12 C10 176.83(17) . . ?
C22 C23 C24 118.03(13) . . ?
C22 C23 H23 120.1(11) . . ?
C24 C23 H23 121.8(11) . . ?
F2 C28 C29 118.68(14) . . ?
F2 C28 C27 118.47(14) . . ?
C29 C28 C27 122.85(12) . . ?
C5 C4 C3 118.20(14) . . ?
C5 C4 H4 121.8(9) . . ?
C3 C4 H4 120.0(9) . . ?
C7 C8 C3 120.72(13) . . ?
C7 C8 C9 131.08(13) . . ?
C3 C8 C9 108.20(11) . . ?
F1 C22 C23 118.58(15) . . ?
F1 C22 C21 118.43(15) . . ?
C23 C22 C21 122.99(13) . . ?
C22 C21 C20 118.52(14) . . ?
C22 C21 H21 120.7(12) . . ?
C20 C21 H21 120.8(12) . . ?
C6 C7 C8 118.13(15) . . ?
C6 C7 H7 120.0(11) . . ?
C8 C7 H7 121.9(11) . . ?
N3 C14 C13 175.67(17) . . ?
N4 C15 C13 178.6(2) . . ?
C6 C5 C4 121.46(15) . . ?
C6 C5 H5 117.5(12) . . ?
C4 C5 H5 121.0(12) . . ?
C5 C6 C7 121.04(15) . . ?
C5 C6 H6 121.2(12) . . ?
C7 C6 H6 117.7(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 C17 C18 C25 171.30(12) . . . . ?
C16 C17 C18 C19 -9.5(2) . . . . ?
C24 C19 C18 C17 -44.50(18) . . . . ?
C20 C19 C18 C17 133.08(13) . . . . ?
C24 C19 C18 C25 134.69(12) . . . . ?
C20 C19 C18 C25 -47.72(16) . . . . ?
C10 C2 C1 C16 42.5(2) . . . . ?
C3 C2 C1 C16 -143.08(13) . . . . ?
C10 C2 C1 C9 -152.67(12) . . . . ?
C3 C2 C1 C9 21.76(13) . . . . ?
C2 C1 C16 C17 162.76(12) . . . . ?
C9 C1 C16 C17 1.4(2) . . . . ?
C18 C17 C16 C1 176.76(13) . . . . ?
C10 C2 C3 C4 -19.0(2) . . . . ?
C1 C2 C3 C4 166.83(14) . . . . ?
C10 C2 C3 C8 162.18(13) . . . . ?
C1 C2 C3 C8 -12.04(14) . . . . ?
C29 C30 C25 C26 1.2(2) . . . . ?
C29 C30 C25 C18 -177.08(12) . . . . ?
C17 C18 C25 C30 149.55(13) . . . . ?
C19 C18 C25 C30 -29.66(17) . . . . ?
C17 C18 C25 C26 -28.67(18) . . . . ?
C19 C18 C25 C26 152.12(12) . . . . ?
C24 C19 C20 C21 1.8(2) . . . . ?
C18 C19 C20 C21 -175.82(13) . . . . ?
C30 C25 C26 C27 -0.9(2) . . . . ?
C18 C25 C26 C27 177.33(12) . . . . ?
C25 C30 C29 C28 -0.6(2) . . . . ?
C14 C13 C9 C1 -7.7(2) . . . . ?
C15 C13 C9 C1 178.77(13) . . . . ?
C14 C13 C9 C8 160.07(13) . . . . ?
C15 C13 C9 C8 -13.4(2) . . . . ?
C16 C1 C9 C13 -49.1(2) . . . . ?
C2 C1 C9 C13 146.80(12) . . . . ?
C16 C1 C9 C8 140.83(14) . . . . ?
C2 C1 C9 C8 -23.29(13) . . . . ?
C20 C19 C24 C23 -1.96(19) . . . . ?
C18 C19 C24 C23 175.67(12) . . . . ?
C3 C2 C10 C12 2.1(2) . . . . ?
C1 C2 C10 C12 175.30(12) . . . . ?
C3 C2 C10 C11 -170.12(12) . . . . ?
C1 C2 C10 C11 3.1(2) . . . . ?
C25 C26 C27 C28 0.1(2) . . . . ?
C19 C24 C23 C22 0.5(2) . . . . ?
C30 C29 C28 F2 179.44(14) . . . . ?
C30 C29 C28 C27 -0.2(2) . . . . ?
C26 C27 C28 F2 -179.20(14) . . . . ?
C26 C27 C28 C29 0.4(2) . . . . ?
C8 C3 C4 C5 1.5(2) . . . . ?
C2 C3 C4 C5 -177.26(14) . . . . ?
C4 C3 C8 C7 -0.7(2) . . . . ?
C2 C3 C8 C7 178.30(13) . . . . ?
C4 C3 C8 C9 178.34(12) . . . . ?
C2 C3 C8 C9 -2.66(14) . . . . ?
C13 C9 C8 C7 25.6(2) . . . . ?
C1 C9 C8 C7 -164.79(15) . . . . ?
C13 C9 C8 C3 -153.27(13) . . . . ?
C1 C9 C8 C3 16.30(14) . . . . ?
C24 C23 C22 F1 -178.76(14) . . . . ?
C24 C23 C22 C21 1.1(2) . . . . ?
F1 C22 C21 C20 178.64(15) . . . . ?
C23 C22 C21 C20 -1.2(3) . . . . ?
C19 C20 C21 C22 -0.3(2) . . . . ?
C3 C8 C7 C6 -0.8(2) . . . . ?
C9 C8 C7 C6 -179.55(15) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
C4 C5 C6 C7 -0.6(3) . . . . ?
C8 C7 C6 C5 1.4(3) . . . . ?

_refine_diff_density_max         0.139
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.055

