# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Roman Dembinski'
_publ_contact_author_email       dembinsk@oakland.edu
loop_
_publ_author_name
D.Borkin
'Mirela Puscau'
'Alena Carlson'
A.Solan
K.Wheeler
'Bela Torok'
'Roman Dembinski'

data_demb21
_database_code_depnum_ccdc_archive 'CCDC 866543'
#TrackingRef '9524_web_deposit_cif_file_0_RomanDembinski_1328974840.DEMB21_pub.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1-(2-fluorophenyl)-5-(4-methylbenzyl)-3-phenyl-1H-pyrazole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H19 F N2'
_chemical_formula_sum            'C23 H19 F N2'
_chemical_formula_weight         342.40

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   5.3015(2)
_cell_length_b                   12.8502(5)
_cell_length_c                   25.7032(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1751.04(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2795
_cell_measurement_theta_min      3.671
_cell_measurement_theta_max      71.030

_exptl_crystal_description       'transparent needle'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7098
_exptl_absorpt_correction_T_max  0.9362
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12795
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.85
_diffrn_reflns_theta_max         68.07
_reflns_number_total             3090
_reflns_number_gt                2770
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SAINT (Bruker, 2008) and XPREP (Bruker, 2008)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

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

All non-hydrogen atoms were located in a difference Fourier map and
refined using anisotropic displacement parameters. The hydrogen atoms
were placed in fixed positions with Ueq = 1.2xUiso of the carbon atom
to which they are attached (Ueq = 1.5xUiso for methyl groups).

Inspection of the difference Fourier map near methyl C25 revealed two
sets of peaks corresponding to a disordered methyl group. Methyl C25
was modeled with the hydrogen atoms disordered over two positions
of equal occupancy (50:50).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0419P)^2^+0.2041P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(18)
_refine_ls_number_reflns         3090
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0799
_refine_ls_wR_factor_gt          0.0767
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.7026(2) 0.88436(7) 0.94584(4) 0.0293(2) Uani 1 1 d . . .
N1 N 0.9646(3) 0.97241(11) 0.86538(5) 0.0225(3) Uani 1 1 d . . .
N2 N 0.7733(3) 0.97142(11) 0.82988(5) 0.0234(3) Uani 1 1 d . . .
C3 C 0.7377(3) 1.07133(13) 0.81774(6) 0.0223(4) Uani 1 1 d . . .
C4 C 0.9051(3) 1.13562(14) 0.84578(6) 0.0241(4) Uani 1 1 d . . .
H4 H 0.9174 1.2093 0.8439 0.029 Uiso 1 1 calc R . .
C5 C 1.0471(3) 1.07030(14) 0.87637(6) 0.0227(4) Uani 1 1 d . . .
C6 C 1.0448(3) 0.87583(13) 0.88772(6) 0.0211(4) Uani 1 1 d . . .
C7 C 0.9046(3) 0.83195(14) 0.92745(6) 0.0226(4) Uani 1 1 d . . .
C8 C 0.9656(4) 0.73637(14) 0.94872(7) 0.0258(4) Uani 1 1 d . . .
H8 H 0.8651 0.7066 0.9755 0.031 Uiso 1 1 calc R . .
C9 C 1.1766(4) 0.68513(14) 0.93008(6) 0.0261(4) Uani 1 1 d . . .
H9 H 1.2215 0.6194 0.9442 0.031 Uiso 1 1 calc R . .
C10 C 1.3231(4) 0.72866(14) 0.89109(7) 0.0266(4) Uani 1 1 d . . .
H10 H 1.4686 0.6932 0.8788 0.032 Uiso 1 1 calc R . .
C11 C 1.2562(3) 0.82446(14) 0.87002(6) 0.0249(4) Uani 1 1 d . . .
H11 H 1.3565 0.8546 0.8434 0.030 Uiso 1 1 calc R . .
C12 C 0.5402(3) 1.10015(13) 0.78025(6) 0.0238(4) Uani 1 1 d . . .
C13 C 0.3860(3) 1.02429(15) 0.75810(6) 0.0278(4) Uani 1 1 d . . .
H13 H 0.4139 0.9531 0.7662 0.033 Uiso 1 1 calc R . .
C14 C 0.1932(4) 1.05106(15) 0.72449(7) 0.0331(4) Uani 1 1 d . . .
H14 H 0.0892 0.9983 0.7100 0.040 Uiso 1 1 calc R . .
C15 C 0.1508(4) 1.15448(16) 0.71187(7) 0.0358(5) Uani 1 1 d . . .
H15 H 0.0181 1.1728 0.6888 0.043 Uiso 1 1 calc R . .
C16 C 0.3025(4) 1.23041(16) 0.73301(8) 0.0361(5) Uani 1 1 d . . .
H16 H 0.2744 1.3014 0.7244 0.043 Uiso 1 1 calc R . .
C17 C 0.4973(4) 1.20365(15) 0.76697(7) 0.0302(4) Uani 1 1 d . . .
H17 H 0.6016 1.2566 0.7812 0.036 Uiso 1 1 calc R . .
C18 C 1.2421(3) 1.09029(13) 0.91700(6) 0.0249(4) Uani 1 1 d . . .
H18A H 1.3174 1.1598 0.9110 0.030 Uiso 1 1 calc R . .
H18B H 1.3780 1.0379 0.9136 0.030 Uiso 1 1 calc R . .
C19 C 1.1359(3) 1.08598(13) 0.97179(6) 0.0235(4) Uani 1 1 d . . .
C20 C 0.9171(3) 1.13998(13) 0.98514(7) 0.0244(4) Uani 1 1 d . . .
H20 H 0.8301 1.1788 0.9593 0.029 Uiso 1 1 calc R . .
C21 C 0.8251(3) 1.13788(13) 1.03549(6) 0.0253(4) Uani 1 1 d . . .
H21 H 0.6768 1.1760 1.0437 0.030 Uiso 1 1 calc R . .
C22 C 0.9451(4) 1.08101(15) 1.07443(6) 0.0268(4) Uani 1 1 d . . .
C23 C 1.1611(4) 1.02651(15) 1.06090(7) 0.0279(4) Uani 1 1 d . . .
H23 H 1.2468 0.9870 1.0866 0.033 Uiso 1 1 calc R . .
C24 C 1.2544(3) 1.02861(14) 1.01051(6) 0.0262(4) Uani 1 1 d . . .
H24 H 1.4021 0.9901 1.0023 0.031 Uiso 1 1 calc R . .
C25 C 0.8375(4) 1.07835(17) 1.12874(7) 0.0372(5) Uani 1 1 d . . .
H25A H 0.6853 1.1215 1.1302 0.056 Uiso 0.50 1 calc PR . .
H25B H 0.9627 1.1053 1.1534 0.056 Uiso 0.50 1 calc PR . .
H25C H 0.7946 1.0065 1.1380 0.056 Uiso 0.50 1 calc PR . .
H25D H 0.9431 1.0340 1.1508 0.056 Uiso 0.50 1 calc PR . .
H25E H 0.6657 1.0503 1.1277 0.056 Uiso 0.50 1 calc PR . .
H25F H 0.8338 1.1490 1.1430 0.056 Uiso 0.50 1 calc PR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0299(6) 0.0271(6) 0.0308(5) 0.0031(4) 0.0069(5) 0.0065(4)
N1 0.0242(7) 0.0215(8) 0.0219(7) 0.0011(6) -0.0016(6) -0.0019(6)
N2 0.0247(7) 0.0246(8) 0.0210(7) 0.0023(6) -0.0021(6) 0.0009(7)
C3 0.0256(9) 0.0223(9) 0.0189(8) 0.0019(6) 0.0049(7) 0.0026(8)
C4 0.0266(9) 0.0209(9) 0.0249(9) 0.0006(7) 0.0041(8) 0.0011(8)
C5 0.0244(8) 0.0225(9) 0.0213(8) -0.0026(6) 0.0049(8) -0.0025(8)
C6 0.0244(9) 0.0177(9) 0.0213(8) -0.0012(6) -0.0046(7) -0.0023(7)
C7 0.0204(8) 0.0245(9) 0.0230(8) -0.0034(7) -0.0008(7) 0.0024(7)
C8 0.0296(9) 0.0242(9) 0.0237(9) 0.0034(7) 0.0011(8) -0.0003(8)
C9 0.0297(9) 0.0228(9) 0.0258(9) 0.0017(7) -0.0041(8) 0.0000(8)
C10 0.0241(9) 0.0266(9) 0.0292(9) -0.0027(7) -0.0011(8) 0.0019(8)
C11 0.0224(9) 0.0285(10) 0.0239(8) 0.0015(7) -0.0004(8) -0.0038(8)
C12 0.0240(9) 0.0284(10) 0.0189(8) 0.0037(7) 0.0058(8) 0.0032(8)
C13 0.0315(9) 0.0303(10) 0.0216(9) 0.0008(7) -0.0002(8) 0.0042(8)
C14 0.0309(10) 0.0432(12) 0.0251(9) -0.0006(7) -0.0010(9) 0.0038(9)
C15 0.0297(10) 0.0526(13) 0.0249(9) 0.0109(8) 0.0011(9) 0.0093(10)
C16 0.0302(10) 0.0389(11) 0.0394(11) 0.0162(9) 0.0067(9) 0.0080(9)
C17 0.0276(10) 0.0288(11) 0.0341(10) 0.0069(7) 0.0052(9) 0.0015(8)
C18 0.0237(9) 0.0214(9) 0.0295(9) -0.0017(7) 0.0003(8) -0.0019(7)
C19 0.0244(9) 0.0181(9) 0.0278(9) -0.0013(7) -0.0020(8) -0.0057(8)
C20 0.0244(9) 0.0211(9) 0.0277(9) 0.0007(7) -0.0044(8) -0.0023(8)
C21 0.0232(9) 0.0219(9) 0.0307(9) -0.0041(7) 0.0018(8) -0.0004(7)
C22 0.0298(9) 0.0249(9) 0.0256(9) -0.0036(7) -0.0014(8) -0.0042(8)
C23 0.0278(9) 0.0291(10) 0.0268(9) 0.0014(7) -0.0062(8) -0.0014(8)
C24 0.0229(9) 0.0224(9) 0.0332(9) -0.0029(7) -0.0022(8) 0.0003(8)
C25 0.0424(12) 0.0411(12) 0.0282(9) -0.0026(8) -0.0002(10) 0.0014(10)

_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 C7 1.351(2) . ?
N1 C5 1.362(2) . ?
N1 N2 1.364(2) . ?
N1 C6 1.432(2) . ?
N2 C3 1.335(2) . ?
C3 C4 1.411(2) . ?
C3 C12 1.470(2) . ?
C4 C5 1.374(3) . ?
C4 H4 0.9500 . ?
C5 C18 1.492(2) . ?
C6 C11 1.378(2) . ?
C6 C7 1.383(2) . ?
C7 C8 1.383(2) . ?
C8 C9 1.383(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C17 1.392(3) . ?
C12 C13 1.394(3) . ?
C13 C14 1.382(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.395(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.518(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C24 1.389(2) . ?
C19 C20 1.394(3) . ?
C20 C21 1.383(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.393(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(3) . ?
C22 C25 1.508(3) . ?
C23 C24 1.387(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C25 H25D 0.9800 . ?
C25 H25E 0.9800 . ?
C25 H25F 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
C5 N1 N2 112.73(14) . . ?
C5 N1 C6 128.46(14) . . ?
N2 N1 C6 118.74(13) . . ?
C3 N2 N1 104.64(13) . . ?
N2 C3 C4 110.77(15) . . ?
N2 C3 C12 119.76(15) . . ?
C4 C3 C12 129.46(15) . . ?
C5 C4 C3 106.22(15) . . ?
C5 C4 H4 126.9 . . ?
C3 C4 H4 126.9 . . ?
N1 C5 C4 105.64(15) . . ?
N1 C5 C18 121.81(15) . . ?
C4 C5 C18 132.44(16) . . ?
C11 C6 C7 119.03(16) . . ?
C11 C6 N1 121.63(15) . . ?
C7 C6 N1 119.33(15) . . ?
F1 C7 C8 119.35(15) . . ?
F1 C7 C6 118.75(15) . . ?
C8 C7 C6 121.90(16) . . ?
C7 C8 C9 118.35(17) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C8 C9 C10 120.76(17) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C11 119.73(17) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C6 C11 C10 120.19(16) . . ?
C6 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C17 C12 C13 118.19(17) . . ?
C17 C12 C3 121.18(16) . . ?
C13 C12 C3 120.60(15) . . ?
C14 C13 C12 121.00(18) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 120.32(19) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 119.51(18) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.32(18) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C12 C17 C16 120.65(18) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C5 C18 C19 112.73(15) . . ?
C5 C18 H18A 109.0 . . ?
C19 C18 H18A 109.0 . . ?
C5 C18 H18B 109.0 . . ?
C19 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C24 C19 C20 117.66(16) . . ?
C24 C19 C18 121.10(16) . . ?
C20 C19 C18 121.24(16) . . ?
C21 C20 C19 120.92(17) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C22 121.43(17) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C23 C22 C21 117.50(16) . . ?
C23 C22 C25 122.21(17) . . ?
C21 C22 C25 120.28(17) . . ?
C24 C23 C22 121.28(17) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C19 121.21(17) . . ?
C23 C24 H24 119.4 . . ?
C19 C24 H24 119.4 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 C25 H25D 109.5 . . ?
H25A C25 H25D 141.1 . . ?
H25B C25 H25D 56.3 . . ?
H25C C25 H25D 56.3 . . ?
C22 C25 H25E 109.5 . . ?
H25A C25 H25E 56.3 . . ?
H25B C25 H25E 141.1 . . ?
H25C C25 H25E 56.3 . . ?
H25D C25 H25E 109.5 . . ?
C22 C25 H25F 109.5 . . ?
H25A C25 H25F 56.3 . . ?
H25B C25 H25F 56.3 . . ?
H25C C25 H25F 141.1 . . ?
H25D C25 H25F 109.5 . . ?
H25E C25 H25F 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
C5 N1 N2 C3 0.90(18) . . . . ?
C6 N1 N2 C3 178.17(14) . . . . ?
N1 N2 C3 C4 -0.36(18) . . . . ?
N1 N2 C3 C12 -179.31(14) . . . . ?
N2 C3 C4 C5 -0.3(2) . . . . ?
C12 C3 C4 C5 178.56(16) . . . . ?
N2 N1 C5 C4 -1.06(18) . . . . ?
C6 N1 C5 C4 -178.01(16) . . . . ?
N2 N1 C5 C18 175.45(14) . . . . ?
C6 N1 C5 C18 -1.5(3) . . . . ?
C3 C4 C5 N1 0.77(18) . . . . ?
C3 C4 C5 C18 -175.21(17) . . . . ?
C5 N1 C6 C11 -83.4(2) . . . . ?
N2 N1 C6 C11 99.80(19) . . . . ?
C5 N1 C6 C7 97.7(2) . . . . ?
N2 N1 C6 C7 -79.09(19) . . . . ?
C11 C6 C7 F1 177.78(14) . . . . ?
N1 C6 C7 F1 -3.3(2) . . . . ?
C11 C6 C7 C8 -2.2(3) . . . . ?
N1 C6 C7 C8 176.68(16) . . . . ?
F1 C7 C8 C9 -178.60(15) . . . . ?
C6 C7 C8 C9 1.4(3) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C7 C6 C11 C10 1.6(2) . . . . ?
N1 C6 C11 C10 -177.32(15) . . . . ?
C9 C10 C11 C6 -0.2(3) . . . . ?
N2 C3 C12 C17 179.65(17) . . . . ?
C4 C3 C12 C17 0.9(3) . . . . ?
N2 C3 C12 C13 1.4(2) . . . . ?
C4 C3 C12 C13 -177.30(17) . . . . ?
C17 C12 C13 C14 -1.0(3) . . . . ?
C3 C12 C13 C14 177.30(15) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C13 C12 C17 C16 1.0(3) . . . . ?
C3 C12 C17 C16 -177.30(17) . . . . ?
C15 C16 C17 C12 -0.4(3) . . . . ?
N1 C5 C18 C19 -77.9(2) . . . . ?
C4 C5 C18 C19 97.5(2) . . . . ?
C5 C18 C19 C24 131.59(17) . . . . ?
C5 C18 C19 C20 -48.9(2) . . . . ?
C24 C19 C20 C21 1.3(3) . . . . ?
C18 C19 C20 C21 -178.30(16) . . . . ?
C19 C20 C21 C22 -0.8(3) . . . . ?
C20 C21 C22 C23 0.1(3) . . . . ?
C20 C21 C22 C25 -178.74(17) . . . . ?
C21 C22 C23 C24 0.1(3) . . . . ?
C25 C22 C23 C24 178.88(18) . . . . ?
C22 C23 C24 C19 0.5(3) . . . . ?
C20 C19 C24 C23 -1.1(3) . . . . ?
C18 C19 C24 C23 178.47(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        68.07
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.035

#===END