# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012
data_global
_journal_name_full Chem.Commun.
_journal_coden_cambridge 0182
_journal_year ?
_journal_volume ?
_journal_page_first ?
_publ_contact_author_name 'Markus Albrecht'
_publ_contact_author_email markus.albrecht@oc.rwth-aachen.de
loop_
_publ_author_name
'Michael Giese'
'Markus Albrecht'
'Tim Krappitz'
'Marius Peters'
'Verena Gossen'
'Gerhard Raabe'
'Arto Valkonen'
'Kari Rissanen'
data_1
_database_code_depnum_ccdc_archive 'CCDC 872223'
#TrackingRef '- 10 cryst 1.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C8 H20 N, C7 H2 F5 N O, Br'
_chemical_formula_sum 'C15 H22 Br F5 N2 O'
_chemical_formula_weight 421.26
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'
F F 0.0171 0.0103 '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'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M P21/n
loop_
_symmetry_equiv_pos_as_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 7.39080(10)
_cell_length_b 10.8170(2)
_cell_length_c 22.6232(4)
_cell_angle_alpha 90.00
_cell_angle_beta 97.6370(10)
_cell_angle_gamma 90.00
_cell_volume 1792.60(5)
_cell_formula_units_Z 4
_cell_measurement_temperature 123(2)
_cell_measurement_reflns_used 4474
_cell_measurement_theta_max 28.283
_cell_measurement_theta_min 0.407
_exptl_crystal_description plate
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.18
_exptl_crystal_size_mid 0.09
_exptl_crystal_size_min 0.07
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.561
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 856
_exptl_absorpt_coefficient_mu 2.346
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.6774
_exptl_absorpt_correction_T_max 0.8530
_exptl_absorpt_process_details 'Sadabs (Sheldrick, 1996)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 123(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 5933
_diffrn_reflns_av_R_equivalents 0.0283
_diffrn_reflns_av_sigmaI/netI 0.0461
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -27
_diffrn_reflns_limit_l_max 27
_diffrn_reflns_theta_min 2.62
_diffrn_reflns_theta_max 25.25
_reflns_number_total 3237
_reflns_number_gt 2623
_reflns_threshold_expression >2\s(I)
_computing_data_collection 'Collect (Bruker, 2008)'
_computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction DENZO-SMN
_computing_structure_solution 'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, et al., 2008)'
_computing_publication_material SHELXL-97
_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^ > 2\s(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.
;
_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^)+(0.0000P)^2^+2.4623P] 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 mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3237
_refine_ls_number_parameters 223
_refine_ls_number_restraints 2
_refine_ls_R_factor_all 0.0497
_refine_ls_R_factor_gt 0.0351
_refine_ls_wR_factor_ref 0.0734
_refine_ls_wR_factor_gt 0.0688
_refine_ls_goodness_of_fit_ref 1.062
_refine_ls_restrained_S_all 1.062
_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
Br1 Br 0.34202(4) 0.25777(3) 0.297732(12) 0.02310(10) Uani 1 1 d . . .
F3 F 0.6941(2) 0.04359(17) 0.40966(9) 0.0360(5) Uani 1 1 d . . .
F4 F 0.7190(2) 0.25354(17) 0.47505(8) 0.0355(4) Uani 1 1 d . . .
F5 F 0.4167(2) 0.34993(16) 0.51388(7) 0.0300(4) Uani 1 1 d . . .
F6 F 0.0933(3) 0.2310(2) 0.49027(10) 0.0534(6) Uani 1 1 d . . .
F7 F 0.0682(3) 0.0213(2) 0.42476(10) 0.0521(6) Uani 1 1 d . . .
O1 O 0.3857(4) -0.1904(2) 0.39434(10) 0.0403(6) Uani 1 1 d . . .
N1 N 0.3204(4) -0.0560(2) 0.31789(11) 0.0256(6) Uani 1 1 d D . .
H1A H 0.289(4) -0.113(2) 0.2898(11) 0.031 Uiso 1 1 d D . .
H1B H 0.303(4) 0.0225(18) 0.3073(14) 0.031 Uiso 1 1 d D . .
N2 N 0.8737(3) 0.5446(2) 0.33790(11) 0.0209(5) Uani 1 1 d . . .
C1 C 0.3640(4) -0.0854(3) 0.37489(13) 0.0222(7) Uani 1 1 d . . .
C2 C 0.3814(4) 0.0260(3) 0.41600(12) 0.0207(6) Uani 1 1 d . . .
C3 C 0.5444(4) 0.0873(3) 0.43016(13) 0.0210(6) Uani 1 1 d . . .
C4 C 0.5588(4) 0.1948(3) 0.46328(13) 0.0216(6) Uani 1 1 d . . .
C5 C 0.4059(4) 0.2427(3) 0.48327(12) 0.0221(6) Uani 1 1 d . . .
C6 C 0.2423(4) 0.1829(3) 0.47080(14) 0.0298(7) Uani 1 1 d . . .
C7 C 0.2318(4) 0.0757(3) 0.43764(14) 0.0286(7) Uani 1 1 d . . .
C8 C 0.8147(4) 0.5480(3) 0.27100(13) 0.0257(7) Uani 1 1 d . . .
H8A H 0.8689 0.6222 0.2547 0.031 Uiso 1 1 calc R . .
H8B H 0.8661 0.4747 0.2530 0.031 Uiso 1 1 calc R . .
C9 C 0.6109(5) 0.5503(3) 0.25151(17) 0.0431(10) Uani 1 1 d . . .
H9A H 0.5869 0.5523 0.2079 0.065 Uiso 1 1 calc R . .
H9B H 0.5582 0.6239 0.2678 0.065 Uiso 1 1 calc R . .
H9C H 0.5554 0.4760 0.2662 0.065 Uiso 1 1 calc R . .
C10 C 0.7992(5) 0.4305(3) 0.36553(14) 0.0270(7) Uani 1 1 d . . .
H10A H 0.8373 0.4330 0.4092 0.032 Uiso 1 1 calc R . .
H10B H 0.6641 0.4342 0.3588 0.032 Uiso 1 1 calc R . .
C11 C 0.8590(5) 0.3088(3) 0.34202(15) 0.0299(7) Uani 1 1 d . . .
H11A H 0.8053 0.2408 0.3624 0.045 Uiso 1 1 calc R . .
H11B H 0.9924 0.3029 0.3493 0.045 Uiso 1 1 calc R . .
H11C H 0.8183 0.3037 0.2991 0.045 Uiso 1 1 calc R . .
C12 C 0.8000(5) 0.6551(3) 0.36819(16) 0.0338(8) Uani 1 1 d . . .
H12A H 0.8373 0.6477 0.4117 0.041 Uiso 1 1 calc R . .
H12B H 0.6650 0.6522 0.3611 0.041 Uiso 1 1 calc R . .
C13 C 0.8620(5) 0.7800(3) 0.34792(16) 0.0386(9) Uani 1 1 d . . .
H13A H 0.8070 0.8457 0.3695 0.058 Uiso 1 1 calc R . .
H13B H 0.8237 0.7895 0.3050 0.058 Uiso 1 1 calc R . .
H13C H 0.9953 0.7856 0.3562 0.058 Uiso 1 1 calc R . .
C14 C 1.0807(4) 0.5442(3) 0.34633(14) 0.0270(7) Uani 1 1 d . . .
H14A H 1.1226 0.4719 0.3250 0.032 Uiso 1 1 calc R . .
H14B H 1.1231 0.6194 0.3273 0.032 Uiso 1 1 calc R . .
C15 C 1.1710(6) 0.5399(4) 0.41021(17) 0.0515(11) Uani 1 1 d . . .
H15A H 1.3039 0.5405 0.4111 0.077 Uiso 1 1 calc R . .
H15B H 1.1341 0.4643 0.4293 0.077 Uiso 1 1 calc R . .
H15C H 1.1335 0.6122 0.4317 0.077 Uiso 1 1 calc R . .
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
Br1 0.02671(17) 0.01864(15) 0.02437(15) 0.00400(13) 0.00497(11) 0.00198(13)
F3 0.0244(10) 0.0344(10) 0.0516(12) -0.0163(9) 0.0144(9) -0.0050(8)
F4 0.0288(10) 0.0369(10) 0.0427(10) -0.0139(9) 0.0116(8) -0.0155(9)
F5 0.0349(11) 0.0270(9) 0.0269(9) -0.0087(8) 0.0001(8) 0.0034(8)
F6 0.0225(10) 0.0682(15) 0.0701(14) -0.0408(13) 0.0090(10) 0.0043(10)
F7 0.0219(11) 0.0620(14) 0.0730(15) -0.0350(12) 0.0082(10) -0.0110(10)
O1 0.0690(18) 0.0184(11) 0.0299(13) 0.0044(10) -0.0061(12) 0.0012(11)
N1 0.0367(16) 0.0180(13) 0.0209(13) -0.0017(11) -0.0006(12) -0.0016(12)
N2 0.0237(14) 0.0138(12) 0.0262(13) -0.0030(10) 0.0073(11) -0.0018(10)
C1 0.0191(16) 0.0206(16) 0.0262(17) 0.0004(13) 0.0006(13) -0.0022(12)
C2 0.0236(17) 0.0220(15) 0.0160(14) 0.0044(12) 0.0011(12) 0.0006(13)
C3 0.0206(16) 0.0219(15) 0.0214(15) 0.0032(12) 0.0061(13) 0.0030(13)
C4 0.0192(16) 0.0234(15) 0.0221(15) 0.0009(13) 0.0023(12) -0.0040(12)
C5 0.0298(17) 0.0197(14) 0.0157(13) -0.0028(13) -0.0013(12) 0.0012(14)
C6 0.0205(18) 0.0397(19) 0.0292(17) -0.0080(15) 0.0038(14) 0.0060(14)
C7 0.0183(17) 0.0372(18) 0.0291(17) -0.0073(15) -0.0011(13) -0.0050(14)
C8 0.0305(19) 0.0205(15) 0.0254(16) 0.0023(13) 0.0015(14) -0.0043(13)
C9 0.035(2) 0.0320(19) 0.058(2) 0.0145(18) -0.0121(18) -0.0113(16)
C10 0.0326(18) 0.0233(16) 0.0269(16) 0.0039(14) 0.0101(14) -0.0034(14)
C11 0.036(2) 0.0188(15) 0.0350(18) 0.0010(14) 0.0066(15) -0.0037(14)
C12 0.042(2) 0.0199(16) 0.043(2) -0.0093(15) 0.0172(16) 0.0056(15)
C13 0.051(2) 0.0203(17) 0.046(2) -0.0086(15) 0.0138(18) -0.0010(15)
C14 0.0248(17) 0.0219(15) 0.0337(18) -0.0013(14) 0.0021(14) -0.0036(13)
C15 0.054(3) 0.039(2) 0.053(2) 0.0029(19) -0.021(2) -0.0085(19)
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
F3 C3 1.341(3) . ?
F4 C4 1.339(3) . ?
F5 C5 1.348(3) . ?
F6 C6 1.344(4) . ?
F7 C7 1.341(4) . ?
O1 C1 1.221(4) . ?
N1 C1 1.326(4) . ?
N1 H1A 0.894(18) . ?
N1 H1B 0.888(18) . ?
N2 C12 1.515(4) . ?
N2 C14 1.516(4) . ?
N2 C8 1.519(4) . ?
N2 C10 1.519(4) . ?
C1 C2 1.518(4) . ?
C2 C3 1.375(4) . ?
C2 C7 1.377(4) . ?
C3 C4 1.380(4) . ?
C4 C5 1.374(4) . ?
C5 C6 1.367(4) . ?
C6 C7 1.378(4) . ?
C8 C9 1.513(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.508(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.517(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.510(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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 H1A 122(2) . . ?
C1 N1 H1B 120(2) . . ?
H1A N1 H1B 117(3) . . ?
C12 N2 C14 111.3(2) . . ?
C12 N2 C8 111.0(2) . . ?
C14 N2 C8 106.1(2) . . ?
C12 N2 C10 106.4(2) . . ?
C14 N2 C10 111.2(2) . . ?
C8 N2 C10 111.0(2) . . ?
O1 C1 N1 125.3(3) . . ?
O1 C1 C2 121.5(3) . . ?
N1 C1 C2 113.3(2) . . ?
C3 C2 C7 116.7(3) . . ?
C3 C2 C1 121.7(3) . . ?
C7 C2 C1 121.4(3) . . ?
F3 C3 C2 119.1(3) . . ?
F3 C3 C4 118.5(3) . . ?
C2 C3 C4 122.3(3) . . ?
F4 C4 C5 120.0(3) . . ?
F4 C4 C3 120.7(3) . . ?
C5 C4 C3 119.3(3) . . ?
F5 C5 C6 120.3(3) . . ?
F5 C5 C4 119.9(3) . . ?
C6 C5 C4 119.8(3) . . ?
F6 C6 C5 119.3(3) . . ?
F6 C6 C7 121.0(3) . . ?
C5 C6 C7 119.7(3) . . ?
F7 C7 C2 119.7(3) . . ?
F7 C7 C6 118.1(3) . . ?
C2 C7 C6 122.1(3) . . ?
C9 C8 N2 115.7(3) . . ?
C9 C8 H8A 108.4 . . ?
N2 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
N2 C8 H8B 108.4 . . ?
H8A C8 H8B 107.4 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N2 115.1(2) . . ?
C11 C10 H10A 108.5 . . ?
N2 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
N2 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C13 115.1(3) . . ?
N2 C12 H12A 108.5 . . ?
C13 C12 H12A 108.5 . . ?
N2 C12 H12B 108.5 . . ?
C13 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 N2 115.5(3) . . ?
C15 C14 H14A 108.4 . . ?
N2 C14 H14A 108.4 . . ?
C15 C14 H14B 108.4 . . ?
N2 C14 H14B 108.4 . . ?
H14A C14 H14B 107.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
O1 C1 C2 C3 91.7(4) . . . . ?
N1 C1 C2 C3 -89.7(3) . . . . ?
O1 C1 C2 C7 -92.8(4) . . . . ?
N1 C1 C2 C7 85.9(4) . . . . ?
C7 C2 C3 F3 -179.3(3) . . . . ?
C1 C2 C3 F3 -3.6(4) . . . . ?
C7 C2 C3 C4 -1.4(4) . . . . ?
C1 C2 C3 C4 174.3(3) . . . . ?
F3 C3 C4 F4 -0.5(4) . . . . ?
C2 C3 C4 F4 -178.4(3) . . . . ?
F3 C3 C4 C5 178.3(3) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
F4 C4 C5 F5 1.1(4) . . . . ?
C3 C4 C5 F5 -177.7(2) . . . . ?
F4 C4 C5 C6 179.6(3) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
F5 C5 C6 F6 -1.1(4) . . . . ?
C4 C5 C6 F6 -179.6(3) . . . . ?
F5 C5 C6 C7 177.7(3) . . . . ?
C4 C5 C6 C7 -0.8(5) . . . . ?
C3 C2 C7 F7 179.1(3) . . . . ?
C1 C2 C7 F7 3.4(4) . . . . ?
C3 C2 C7 C6 1.4(5) . . . . ?
C1 C2 C7 C6 -174.4(3) . . . . ?
F6 C6 C7 F7 0.7(5) . . . . ?
C5 C6 C7 F7 -178.1(3) . . . . ?
F6 C6 C7 C2 178.5(3) . . . . ?
C5 C6 C7 C2 -0.3(5) . . . . ?
C12 N2 C8 C9 -58.4(3) . . . . ?
C14 N2 C8 C9 -179.4(3) . . . . ?
C10 N2 C8 C9 59.7(3) . . . . ?
C12 N2 C10 C11 -179.2(3) . . . . ?
C14 N2 C10 C11 -57.8(3) . . . . ?
C8 N2 C10 C11 60.0(3) . . . . ?
C14 N2 C12 C13 57.4(4) . . . . ?
C8 N2 C12 C13 -60.4(4) . . . . ?
C10 N2 C12 C13 178.7(3) . . . . ?
C12 N2 C14 C15 59.7(3) . . . . ?
C8 N2 C14 C15 -179.5(3) . . . . ?
C10 N2 C14 C15 -58.8(3) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Br1 0.89(2) 2.51(2) 3.392(3) 169(3) 2_545
N1 H1B Br1 0.89(2) 2.57(2) 3.431(3) 163(3) .
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.365
_refine_diff_density_min -0.343
_refine_diff_density_rms 0.070
# Attachment '- cryst 2c.cif'
data_2c
_database_code_depnum_ccdc_archive 'CCDC 872224'
#TrackingRef '- cryst 2c.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C20 H6 F10 N2 O2'
_chemical_formula_sum 'C20 H6 F10 N2 O2'
_chemical_formula_weight 496.27
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 4.9394(2)
_cell_length_b 10.5985(5)
_cell_length_c 17.8123(8)
_cell_angle_alpha 101.134(3)
_cell_angle_beta 97.114(2)
_cell_angle_gamma 91.720(3)
_cell_volume 906.49(7)
_cell_formula_units_Z 2
_cell_measurement_temperature 123(2)
_cell_measurement_reflns_used 3654
_cell_measurement_theta_max 28.283
_cell_measurement_theta_min 0.407
_exptl_crystal_description stick
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.07
_exptl_crystal_size_min 0.02
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.818
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 492
_exptl_absorpt_coefficient_mu 0.188
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9545
_exptl_absorpt_correction_T_max 0.9962
_exptl_absorpt_process_details 'Sadabs (Sheldrick, 1996)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 123(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 3248
_diffrn_reflns_av_R_equivalents 0.0738
_diffrn_reflns_av_sigmaI/netI 0.0812
_diffrn_reflns_limit_h_min -5
_diffrn_reflns_limit_h_max 5
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -21
_diffrn_reflns_limit_l_max 21
_diffrn_reflns_theta_min 1.96
_diffrn_reflns_theta_max 25.25
_reflns_number_total 3248
_reflns_number_gt 2127
_reflns_threshold_expression >2\s(I)
_computing_data_collection 'Collect (Bruker, 2008)'
_computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction DENZO-SMN
_computing_structure_solution 'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, et al., 2008)'
_computing_publication_material SHELXL-97
_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^ > 2\s(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. Due to observed
non-merohedral twinning of the crystal with two domains the HKLF5 method
refinement was utilized with obtained BASF parameter value of 0.16285.
;
_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^)+(0.0336P)^2^+1.5756P] 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 mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3248
_refine_ls_number_parameters 314
_refine_ls_number_restraints 2
_refine_ls_R_factor_all 0.1060
_refine_ls_R_factor_gt 0.0612
_refine_ls_wR_factor_ref 0.1375
_refine_ls_wR_factor_gt 0.1198
_refine_ls_goodness_of_fit_ref 1.065
_refine_ls_restrained_S_all 1.064
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F9 F 0.7365(5) 0.2432(2) 0.33318(14) 0.0340(6) Uani 1 1 d . . .
F10 F 0.5581(5) 0.1587(3) 0.45200(14) 0.0412(7) Uani 1 1 d . . .
F11 F 0.1391(6) -0.0239(3) 0.42588(15) 0.0436(7) Uani 1 1 d . . .
F12 F -0.0812(5) -0.1296(3) 0.27906(16) 0.0423(7) Uani 1 1 d . . .
F13 F 0.1130(5) -0.0559(2) 0.15965(13) 0.0291(6) Uani 1 1 d . . .
F16 F 1.2432(5) 0.4076(2) 0.31699(15) 0.0332(6) Uani 1 1 d . . .
F17 F 1.2645(5) 0.5329(3) 0.46420(15) 0.0396(7) Uani 1 1 d . . .
F18 F 0.9127(5) 0.7181(3) 0.50277(13) 0.0362(6) Uani 1 1 d . . .
F19 F 0.5403(5) 0.7814(2) 0.39164(13) 0.0288(6) Uani 1 1 d . . .
F20 F 0.5176(4) 0.6603(2) 0.24522(12) 0.0242(5) Uani 1 1 d . . .
O7 O 0.7813(5) 0.1514(3) 0.17346(17) 0.0289(7) Uani 1 1 d . . .
O14 O 1.0949(5) 0.4455(3) 0.16568(17) 0.0317(7) Uani 1 1 d . . .
N1 N 0.3449(6) 0.1807(3) 0.12443(18) 0.0191(7) Uani 1 1 d D . .
H1 H 0.165(4) 0.177(4) 0.130(2) 0.023 Uiso 1 1 d D . .
N2 N 0.6348(6) 0.4165(3) 0.15410(19) 0.0199(7) Uani 1 1 d D . .
H2N H 0.486(6) 0.437(4) 0.177(2) 0.024 Uiso 1 1 d D . .
C1 C 0.4295(8) 0.2313(4) 0.0616(2) 0.0194(9) Uani 1 1 d . . .
C2 C 0.3563(8) 0.1657(4) -0.0137(2) 0.0234(9) Uani 1 1 d . . .
H2 H 0.2403 0.0895 -0.0244 0.028 Uiso 1 1 calc R . .
C3 C 0.4546(9) 0.2127(4) -0.0736(2) 0.0281(10) Uani 1 1 d . . .
H3 H 0.4009 0.1699 -0.1256 0.034 Uiso 1 1 calc R . .
C4 C 0.6287(8) 0.3206(4) -0.0579(2) 0.0289(10) Uani 1 1 d . . .
H4 H 0.7020 0.3495 -0.0989 0.035 Uiso 1 1 calc R . .
C5 C 0.6988(8) 0.3882(4) 0.0175(2) 0.0233(9) Uani 1 1 d . . .
H5 H 0.8181 0.4633 0.0281 0.028 Uiso 1 1 calc R . .
C6 C 0.5931(8) 0.3448(4) 0.0768(2) 0.0190(9) Uani 1 1 d . . .
C7 C 0.5344(8) 0.1453(4) 0.1765(2) 0.0200(9) Uani 1 1 d . . .
C8 C 0.4270(8) 0.0979(4) 0.2427(2) 0.0204(9) Uani 1 1 d . . .
C9 C 0.5372(8) 0.1488(4) 0.3177(2) 0.0238(9) Uani 1 1 d . . .
C10 C 0.4437(8) 0.1071(4) 0.3795(2) 0.0277(10) Uani 1 1 d . . .
C11 C 0.2346(9) 0.0150(4) 0.3664(3) 0.0292(10) Uani 1 1 d . . .
C12 C 0.1219(8) -0.0380(4) 0.2921(3) 0.0262(10) Uani 1 1 d . . .
C13 C 0.2201(8) 0.0030(4) 0.2314(2) 0.0202(9) Uani 1 1 d . . .
C14 C 0.8799(8) 0.4599(4) 0.1929(2) 0.0221(9) Uani 1 1 d . . .
C15 C 0.8801(7) 0.5285(4) 0.2755(2) 0.0190(9) Uani 1 1 d . . .
C16 C 1.0676(8) 0.5004(4) 0.3339(2) 0.0233(9) Uani 1 1 d . . .
C17 C 1.0798(8) 0.5633(4) 0.4093(2) 0.0267(10) Uani 1 1 d . . .
C18 C 0.9007(8) 0.6566(4) 0.4295(2) 0.0255(10) Uani 1 1 d . . .
C19 C 0.7123(8) 0.6875(4) 0.3731(2) 0.0220(9) Uani 1 1 d . . .
C20 C 0.7029(8) 0.6236(4) 0.2977(2) 0.0186(9) Uani 1 1 d . . .
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
F9 0.0266(13) 0.0388(16) 0.0327(14) 0.0027(12) -0.0015(11) -0.0103(12)
F10 0.0381(15) 0.0630(19) 0.0215(13) 0.0073(12) 0.0007(12) 0.0060(13)
F11 0.0476(16) 0.0543(19) 0.0404(16) 0.0271(14) 0.0211(13) 0.0089(14)
F12 0.0418(16) 0.0343(16) 0.0546(17) 0.0169(13) 0.0120(14) -0.0127(13)
F13 0.0280(13) 0.0263(14) 0.0298(13) -0.0001(11) 0.0022(11) -0.0045(11)
F16 0.0227(13) 0.0310(15) 0.0443(15) 0.0051(12) -0.0005(11) 0.0110(11)
F17 0.0314(14) 0.0508(18) 0.0350(15) 0.0123(13) -0.0094(12) 0.0072(12)
F18 0.0360(15) 0.0459(17) 0.0233(13) 0.0012(12) -0.0006(11) 0.0029(12)
F19 0.0321(13) 0.0287(14) 0.0247(13) 0.0014(10) 0.0050(11) 0.0091(11)
F20 0.0239(12) 0.0250(13) 0.0228(12) 0.0042(10) -0.0002(10) 0.0060(10)
O7 0.0180(16) 0.0380(19) 0.0347(17) 0.0166(14) 0.0043(13) 0.0033(13)
O14 0.0121(14) 0.043(2) 0.0355(17) -0.0043(14) 0.0061(13) -0.0013(13)
N1 0.0152(16) 0.024(2) 0.0184(17) 0.0070(14) 0.0010(15) 0.0007(15)
N2 0.0134(17) 0.0222(19) 0.0229(18) 0.0006(15) 0.0042(14) -0.0002(14)
C1 0.019(2) 0.021(2) 0.020(2) 0.0054(17) 0.0078(17) 0.0061(17)
C2 0.022(2) 0.023(2) 0.024(2) 0.0011(18) 0.0035(18) -0.0017(18)
C3 0.029(2) 0.037(3) 0.017(2) 0.0026(19) 0.0019(19) 0.002(2)
C4 0.026(2) 0.043(3) 0.022(2) 0.011(2) 0.0097(19) 0.009(2)
C5 0.018(2) 0.027(2) 0.027(2) 0.0074(19) 0.0054(18) 0.0013(18)
C6 0.0162(19) 0.019(2) 0.020(2) -0.0002(17) 0.0026(17) 0.0031(17)
C7 0.022(2) 0.019(2) 0.019(2) 0.0054(17) 0.0005(18) -0.0002(17)
C8 0.017(2) 0.021(2) 0.024(2) 0.0061(17) 0.0040(17) 0.0014(17)
C9 0.018(2) 0.026(2) 0.027(2) 0.0044(18) 0.0024(18) 0.0007(18)
C10 0.024(2) 0.037(3) 0.021(2) 0.0053(19) -0.0010(18) 0.007(2)
C11 0.033(2) 0.029(3) 0.033(3) 0.017(2) 0.014(2) 0.009(2)
C12 0.024(2) 0.021(2) 0.036(3) 0.0101(19) 0.007(2) -0.0010(19)
C13 0.018(2) 0.020(2) 0.022(2) 0.0020(17) 0.0028(17) 0.0006(17)
C14 0.017(2) 0.024(2) 0.025(2) 0.0037(18) 0.0034(18) 0.0015(17)
C15 0.0097(19) 0.023(2) 0.024(2) 0.0055(17) 0.0003(16) -0.0027(16)
C16 0.016(2) 0.022(2) 0.031(2) 0.0027(19) 0.0028(18) -0.0018(17)
C17 0.018(2) 0.031(3) 0.033(3) 0.014(2) -0.0032(19) -0.0020(19)
C18 0.027(2) 0.028(3) 0.021(2) 0.0031(18) 0.0022(18) -0.0010(19)
C19 0.021(2) 0.019(2) 0.027(2) 0.0040(18) 0.0069(18) 0.0033(17)
C20 0.0145(19) 0.019(2) 0.022(2) 0.0076(17) -0.0032(17) -0.0039(16)
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
F9 C9 1.346(5) . ?
F10 C10 1.348(5) . ?
F11 C11 1.339(5) . ?
F12 C12 1.342(5) . ?
F13 C13 1.344(4) . ?
F16 C16 1.346(5) . ?
F17 C17 1.345(5) . ?
F18 C18 1.335(5) . ?
F19 C19 1.347(4) . ?
F20 C20 1.346(4) . ?
O7 C7 1.228(5) . ?
O14 C14 1.223(5) . ?
N1 C7 1.348(5) . ?
N1 C1 1.431(5) . ?
N1 H1 0.908(19) . ?
N2 C14 1.339(5) . ?
N2 C6 1.426(5) . ?
N2 H2N 0.899(19) . ?
C1 C2 1.385(5) . ?
C1 C6 1.391(6) . ?
C2 C3 1.394(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.372(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(5) . ?
C5 H5 0.9500 . ?
C7 C8 1.513(5) . ?
C8 C9 1.377(6) . ?
C8 C13 1.380(6) . ?
C9 C10 1.386(6) . ?
C10 C11 1.366(6) . ?
C11 C12 1.375(6) . ?
C12 C13 1.375(6) . ?
C14 C15 1.509(6) . ?
C15 C16 1.387(6) . ?
C15 C20 1.387(5) . ?
C16 C17 1.373(6) . ?
C17 C18 1.372(6) . ?
C18 C19 1.377(6) . ?
C19 C20 1.376(6) . ?
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
C7 N1 C1 119.6(3) . . ?
C7 N1 H1 121(3) . . ?
C1 N1 H1 119(3) . . ?
C14 N2 C6 124.2(3) . . ?
C14 N2 H2N 118(3) . . ?
C6 N2 H2N 118(3) . . ?
C2 C1 C6 120.1(4) . . ?
C2 C1 N1 120.3(4) . . ?
C6 C1 N1 119.5(3) . . ?
C1 C2 C3 119.3(4) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.7(4) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 119.2(4) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 120.3(4) . . ?
C5 C6 N2 121.9(4) . . ?
C1 C6 N2 117.7(3) . . ?
O7 C7 N1 124.1(3) . . ?
O7 C7 C8 119.9(3) . . ?
N1 C7 C8 116.0(3) . . ?
C9 C8 C13 117.3(4) . . ?
C9 C8 C7 120.1(4) . . ?
C13 C8 C7 122.6(4) . . ?
F9 C9 C8 120.6(4) . . ?
F9 C9 C10 117.9(4) . . ?
C8 C9 C10 121.5(4) . . ?
F10 C10 C11 120.5(4) . . ?
F10 C10 C9 119.7(4) . . ?
C11 C10 C9 119.8(4) . . ?
F11 C11 C10 120.2(4) . . ?
F11 C11 C12 119.9(4) . . ?
C10 C11 C12 119.9(4) . . ?
F12 C12 C13 120.4(4) . . ?
F12 C12 C11 120.0(4) . . ?
C13 C12 C11 119.5(4) . . ?
F13 C13 C12 117.5(3) . . ?
F13 C13 C8 120.5(3) . . ?
C12 C13 C8 122.0(4) . . ?
O14 C14 N2 124.0(4) . . ?
O14 C14 C15 120.2(3) . . ?
N2 C14 C15 115.8(3) . . ?
C16 C15 C20 116.1(4) . . ?
C16 C15 C14 120.5(4) . . ?
C20 C15 C14 123.3(3) . . ?
F16 C16 C17 118.1(4) . . ?
F16 C16 C15 119.6(4) . . ?
C17 C16 C15 122.3(4) . . ?
F17 C17 C18 119.4(4) . . ?
F17 C17 C16 120.4(4) . . ?
C18 C17 C16 120.1(4) . . ?
F18 C18 C17 120.3(4) . . ?
F18 C18 C19 120.5(4) . . ?
C17 C18 C19 119.2(4) . . ?
F19 C19 C20 120.2(3) . . ?
F19 C19 C18 119.9(4) . . ?
C20 C19 C18 119.9(4) . . ?
F20 C20 C19 116.9(3) . . ?
F20 C20 C15 120.8(3) . . ?
C19 C20 C15 122.3(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 N1 C1 C2 116.1(4) . . . . ?
C7 N1 C1 C6 -61.9(5) . . . . ?
C6 C1 C2 C3 1.8(6) . . . . ?
N1 C1 C2 C3 -176.2(4) . . . . ?
C1 C2 C3 C4 2.0(6) . . . . ?
C2 C3 C4 C5 -3.2(6) . . . . ?
C3 C4 C5 C6 0.6(6) . . . . ?
C4 C5 C6 C1 3.2(6) . . . . ?
C4 C5 C6 N2 -173.6(4) . . . . ?
C2 C1 C6 C5 -4.4(6) . . . . ?
N1 C1 C6 C5 173.6(4) . . . . ?
C2 C1 C6 N2 172.5(4) . . . . ?
N1 C1 C6 N2 -9.5(5) . . . . ?
C14 N2 C6 C5 -52.8(6) . . . . ?
C14 N2 C6 C1 130.3(4) . . . . ?
C1 N1 C7 O7 -1.2(6) . . . . ?
C1 N1 C7 C8 177.7(4) . . . . ?
O7 C7 C8 C9 49.8(6) . . . . ?
N1 C7 C8 C9 -129.2(4) . . . . ?
O7 C7 C8 C13 -129.7(4) . . . . ?
N1 C7 C8 C13 51.3(5) . . . . ?
C13 C8 C9 F9 -178.9(4) . . . . ?
C7 C8 C9 F9 1.6(6) . . . . ?
C13 C8 C9 C10 -0.3(6) . . . . ?
C7 C8 C9 C10 -179.8(4) . . . . ?
F9 C9 C10 F10 -1.8(6) . . . . ?
C8 C9 C10 F10 179.6(4) . . . . ?
F9 C9 C10 C11 177.5(4) . . . . ?
C8 C9 C10 C11 -1.1(6) . . . . ?
F10 C10 C11 F11 0.7(6) . . . . ?
C9 C10 C11 F11 -178.6(4) . . . . ?
F10 C10 C11 C12 -179.3(4) . . . . ?
C9 C10 C11 C12 1.4(6) . . . . ?
F11 C11 C12 F12 -0.8(6) . . . . ?
C10 C11 C12 F12 179.2(4) . . . . ?
F11 C11 C12 C13 179.7(4) . . . . ?
C10 C11 C12 C13 -0.4(6) . . . . ?
F12 C12 C13 F13 -2.7(6) . . . . ?
C11 C12 C13 F13 176.8(4) . . . . ?
F12 C12 C13 C8 179.4(4) . . . . ?
C11 C12 C13 C8 -1.1(6) . . . . ?
C9 C8 C13 F13 -176.4(4) . . . . ?
C7 C8 C13 F13 3.1(6) . . . . ?
C9 C8 C13 C12 1.4(6) . . . . ?
C7 C8 C13 C12 -179.1(4) . . . . ?
C6 N2 C14 O14 1.9(6) . . . . ?
C6 N2 C14 C15 -177.2(4) . . . . ?
O14 C14 C15 C16 -45.0(6) . . . . ?
N2 C14 C15 C16 134.2(4) . . . . ?
O14 C14 C15 C20 133.4(4) . . . . ?
N2 C14 C15 C20 -47.5(5) . . . . ?
C20 C15 C16 F16 178.9(3) . . . . ?
C14 C15 C16 F16 -2.7(6) . . . . ?
C20 C15 C16 C17 -0.4(6) . . . . ?
C14 C15 C16 C17 178.0(4) . . . . ?
F16 C16 C17 F17 0.6(6) . . . . ?
C15 C16 C17 F17 179.9(4) . . . . ?
F16 C16 C17 C18 -178.6(4) . . . . ?
C15 C16 C17 C18 0.7(6) . . . . ?
F17 C17 C18 F18 1.1(6) . . . . ?
C16 C17 C18 F18 -179.8(4) . . . . ?
F17 C17 C18 C19 179.9(4) . . . . ?
C16 C17 C18 C19 -1.0(6) . . . . ?
F18 C18 C19 F19 0.6(6) . . . . ?
C17 C18 C19 F19 -178.2(4) . . . . ?
F18 C18 C19 C20 179.8(4) . . . . ?
C17 C18 C19 C20 0.9(6) . . . . ?
F19 C19 C20 F20 0.4(5) . . . . ?
C18 C19 C20 F20 -178.7(3) . . . . ?
F19 C19 C20 C15 178.4(4) . . . . ?
C18 C19 C20 C15 -0.7(6) . . . . ?
C16 C15 C20 F20 178.4(3) . . . . ?
C14 C15 C20 F20 0.0(6) . . . . ?
C16 C15 C20 C19 0.4(6) . . . . ?
C14 C15 C20 C19 -178.0(4) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O7 0.91(2) 2.16(2) 3.044(4) 163(4) 1_455
N2 H2N O14 0.90(2) 1.93(3) 2.722(4) 147(4) 1_455
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full 25.25
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max 0.337
_refine_diff_density_min -0.297
_refine_diff_density_rms 0.075