#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:25:50 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180298 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/12/7151275.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7151275
loop_
_publ_author_name
'Berkessel, Albrecht'
'Mukherjee, Santanu'
'Müller, Thomas N'
'Cleemann, Felix'
'Roland, Katrin'
'Brandenburg, Marc'
'Neudörfl, Jörg-M'
'Lex, Johann'
_publ_section_title
;
 Structural optimization of thiourea-based bifunctional organocatalysts
 for the highly enantioselective dynamic kinetic resolution of
 azlactones.
;
_journal_issue                   23
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4319
_journal_page_last               4330
_journal_paper_doi               10.1039/b607574f
_journal_volume                  4
_journal_year                    2006
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C20 H21 F6 N3 O'
_chemical_formula_sum            'C20 H21 F6 N3 O'
_chemical_formula_weight         433.40
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.724(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5778(9)
_cell_length_b                   18.5187(16)
_cell_length_c                   11.1532(13)
_cell_measurement_reflns_used    12334
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      1.96
_cell_volume                     2146.6(4)
_computing_cell_refinement       'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       Phi/Omega-Scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0972
_diffrn_reflns_av_sigmaI/netI    0.1262
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12334
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     618
_refine_ls_number_reflns         4834
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1530
_refine_ls_R_factor_gt           0.0629
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0648P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1434
_reflns_number_gt                2571
_reflns_number_total             4834
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b607574f.txt
_cod_data_source_block           9
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7151275
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
C1 C 0.3181(7) 0.2325(3) 0.2481(6) 0.0569(19) Uani 1 1 d . . .
H1A H 0.3669 0.1939 0.2216 0.068 Uiso 1 1 calc R . .
H1B H 0.3737 0.2729 0.2732 0.068 Uiso 1 1 calc R . .
H1C H 0.2510 0.2468 0.1822 0.068 Uiso 1 1 calc R . .
C2 C 0.2589(6) 0.2069(3) 0.3553(6) 0.0371(15) Uani 1 1 d . . .
H2 H 0.320(5) 0.200(2) 0.431(5) 0.021(13) Uiso 1 1 d . . .
C3 C 0.1699(6) 0.2646(3) 0.3944(5) 0.0347(14) Uani 1 1 d . . .
H3 H 0.1098 0.2808 0.3217 0.042 Uiso 1 1 calc . . .
C4 C 0.2495(6) 0.3923(3) 0.3789(7) 0.0464(17) Uani 1 1 d . . .
H4 H 0.195(7) 0.395(4) 0.298(7) 0.08(2) Uiso 1 1 d . . .
C5 C 0.3271(8) 0.4495(4) 0.4258(9) 0.063(2) Uani 1 1 d . . .
H5 H 0.326(7) 0.490(4) 0.376(7) 0.08(2) Uiso 1 1 d . . .
C6 C 0.4013(7) 0.4461(3) 0.5391(9) 0.064(2) Uani 1 1 d . . .
H6 H 0.4524 0.4853 0.5692 0.077 Uiso 1 1 calc . . .
C7 C 0.4014(7) 0.3842(4) 0.6110(9) 0.060(2) Uani 1 1 d . . .
H7 H 0.449(7) 0.374(3) 0.688(6) 0.06(2) Uiso 1 1 d . . .
C8 C 0.3232(6) 0.3258(3) 0.5635(6) 0.0430(16) Uani 1 1 d . . .
H8 H 0.3223 0.2843 0.6103 0.052 Uiso 1 1 calc . . .
C9 C 0.2481(5) 0.3288(3) 0.4488(6) 0.0382(15) Uani 1 1 d . . .
C10 C 0.0041(6) 0.2660(3) 0.5216(5) 0.0304(14) Uani 1 1 d . . .
C11 C -0.1714(6) 0.2413(3) 0.6347(5) 0.0308(13) Uani 1 1 d . . .
C12 C -0.2695(6) 0.1934(3) 0.6449(5) 0.0316(14) Uani 1 1 d . . .
H12 H -0.272(5) 0.154(3) 0.593(5) 0.039(16) Uiso 1 1 d . . .
C13 C -0.3555(6) 0.2068(3) 0.7200(5) 0.0360(15) Uani 1 1 d . . .
C14 C -0.3442(7) 0.2691(3) 0.7916(6) 0.0412(16) Uani 1 1 d . . .
H14 H -0.392(5) 0.277(3) 0.851(5) 0.029(15) Uiso 1 1 d . . .
C15 C -0.2467(6) 0.3177(3) 0.7804(5) 0.0371(15) Uani 1 1 d . . .
C16 C -0.1614(6) 0.3045(3) 0.7052(5) 0.0316(14) Uani 1 1 d . . .
H16 H -0.0963 0.3375 0.7006 0.038 Uiso 1 1 calc . . .
C17 C -0.2300(7) 0.3839(3) 0.8620(6) 0.0465(16) Uani 1 1 d . . .
C18 C -0.4570(6) 0.1525(3) 0.7292(6) 0.0447(16) Uani 1 1 d . . .
C19 C 0.0973(6) 0.1325(4) 0.2236(6) 0.0564(18) Uani 1 1 d . . .
H19A H 0.1408 0.1355 0.1555 0.068 Uiso 1 1 calc R . .
H19B H 0.0369 0.1716 0.2198 0.068 Uiso 1 1 calc R . .
H19C H 0.0523 0.0874 0.2209 0.068 Uiso 1 1 calc R . .
C20 C 0.2768(7) 0.0761(3) 0.3483(6) 0.0567(19) Uani 1 1 d . . .
H20A H 0.2293 0.0325 0.3551 0.068 Uiso 1 1 calc R . .
H20B H 0.3417 0.0820 0.4202 0.068 Uiso 1 1 calc R . .
H20C H 0.3169 0.0731 0.2780 0.068 Uiso 1 1 calc R . .
N1 N 0.1900(4) 0.1372(2) 0.3357(4) 0.0361(12) Uani 1 1 d . . .
N2 N 0.0967(4) 0.2313(2) 0.4765(4) 0.0323(12) Uani 1 1 d . . .
H2N H 0.094(5) 0.187(3) 0.471(5) 0.039 Uiso 1 1 d . . .
N3 N -0.0829(5) 0.2225(2) 0.5635(5) 0.0338(13) Uani 1 1 d . . .
H3N H -0.066(6) 0.187(3) 0.564(5) 0.041 Uiso 1 1 d . . .
O1 O -0.0037(4) 0.33273(17) 0.5258(3) 0.0339(9) Uani 1 1 d . . .
F1 F -0.4101(3) 0.09409(17) 0.7922(3) 0.0572(10) Uani 1 1 d . . .
F2 F -0.5151(4) 0.1288(2) 0.6210(4) 0.0743(13) Uani 1 1 d . . .
F3 F -0.5494(4) 0.1780(2) 0.7847(4) 0.0759(13) Uani 1 1 d . . .
F4 F -0.3374(5) 0.4214(2) 0.8526(5) 0.1080(19) Uani 1 1 d . . .
F5 F -0.1901(5) 0.3676(2) 0.9759(4) 0.0945(17) Uani 1 1 d . . .
F6 F -0.1448(5) 0.43050(19) 0.8341(4) 0.0824(14) Uani 1 1 d . . .
C21 C 0.3222(6) -0.0086(3) -0.1493(5) 0.0427(16) Uani 1 1 d . . .
H21A H 0.3668 -0.0469 -0.1012 0.051 Uiso 1 1 calc R . .
H21B H 0.2915 0.0256 -0.0967 0.051 Uiso 1 1 calc R . .
H21C H 0.3797 0.0151 -0.1938 0.051 Uiso 1 1 calc R . .
C22 C 0.2092(5) -0.0394(3) -0.2382(5) 0.0291(13) Uani 1 1 d . . .
H22 H 0.149(5) -0.065(3) -0.190(5) 0.046(17) Uiso 1 1 d . . .
C23 C 0.1330(5) 0.0200(3) -0.3181(5) 0.0309(14) Uani 1 1 d . . .
H23 H 0.186(5) 0.046(3) -0.361(5) 0.037 Uiso 1 1 d . . .
C24 C 0.1226(6) 0.1394(3) -0.2110(6) 0.0394(15) Uani 1 1 d . . .
H24 H 0.191(6) 0.153(3) -0.254(5) 0.047(18) Uiso 1 1 d . . .
C25 C 0.0684(8) 0.1833(4) -0.1321(7) 0.055(2) Uani 1 1 d . . .
H25 H 0.116(6) 0.220(3) -0.122(5) 0.041(19) Uiso 1 1 d . . .
C26 C -0.0331(8) 0.1621(4) -0.0828(6) 0.0521(19) Uani 1 1 d . . .
H26 H -0.084(5) 0.188(3) -0.029(5) 0.039(16) Uiso 1 1 d . . .
C27 C -0.0853(7) 0.0943(4) -0.1108(6) 0.0501(17) Uani 1 1 d . . .
H27 H -0.173(8) 0.079(4) -0.076(7) 0.10(3) Uiso 1 1 d . . .
C28 C -0.0338(6) 0.0500(3) -0.1895(6) 0.0426(16) Uani 1 1 d . . .
H28 H -0.0702 0.0048 -0.2084 0.051 Uiso 1 1 calc . . .
C29 C 0.0694(6) 0.0707(3) -0.2410(5) 0.0329(14) Uani 1 1 d . . .
C30 C -0.0292(5) 0.0163(3) -0.5081(5) 0.0283(13) Uani 1 1 d . . .
C31 C -0.1682(6) -0.0133(3) -0.7067(5) 0.0299(13) Uani 1 1 d . . .
C32 C -0.1951(6) -0.0672(3) -0.7953(5) 0.0361(15) Uani 1 1 d . . .
H32 H -0.157(4) -0.113(3) -0.777(4) 0.018(12) Uiso 1 1 d . . .
C33 C -0.2781(6) -0.0563(3) -0.9028(5) 0.0352(14) Uani 1 1 d . . .
C34 C -0.3396(6) 0.0100(3) -0.9297(6) 0.0348(14) Uani 1 1 d . . .
H34 H -0.393(5) 0.017(3) -1.008(6) 0.042 Uiso 1 1 d . . .
C35 C -0.3102(5) 0.0647(3) -0.8437(5) 0.0314(14) Uani 1 1 d . . .
C36 C -0.2272(5) 0.0540(3) -0.7338(5) 0.0322(13) Uani 1 1 d . . .
H36 H -0.213(5) 0.088(3) -0.670(5) 0.041(16) Uiso 1 1 d . . .
C37 C -0.3721(7) 0.1379(3) -0.8704(6) 0.0455(16) Uani 1 1 d . . .
C38 C -0.3061(8) -0.1170(4) -0.9931(7) 0.062(2) Uani 1 1 d . . .
C39 C 0.3457(7) -0.0822(4) -0.3803(6) 0.059(2) Uani 1 1 d . . .
H39A H 0.4253 -0.0802 -0.3227 0.064(8) Uiso 1 1 calc R . .
H39B H 0.3306 -0.0365 -0.4212 0.064(8) Uiso 1 1 calc R . .
H39C H 0.3505 -0.1194 -0.4392 0.064(8) Uiso 1 1 calc R . .
C40 C 0.2589(7) -0.1677(3) -0.2563(6) 0.0547(19) Uani 1 1 d . . .
H40A H 0.2664 -0.2044 -0.3153 0.064(8) Uiso 1 1 calc R . .
H40B H 0.1863 -0.1780 -0.2187 0.064(8) Uiso 1 1 calc R . .
H40C H 0.3358 -0.1668 -0.1950 0.064(8) Uiso 1 1 calc R . .
N4 N 0.2410(5) -0.0978(2) -0.3165(4) 0.0409(13) Uani 1 1 d . . .
N5 N 0.0393(5) -0.0170(2) -0.4107(4) 0.0328(12) Uani 1 1 d . . .
H5N H 0.055(6) -0.056(3) -0.410(5) 0.039 Uiso 1 1 d . . .
N6 N -0.0869(5) -0.0291(2) -0.5985(4) 0.0320(13) Uani 1 1 d . . .
H6N H -0.079(6) -0.064(3) -0.580(5) 0.038 Uiso 1 1 d . . .
O2 O -0.0431(4) 0.08302(18) -0.5154(3) 0.0354(10) Uani 1 1 d . . .
F7 F -0.1966(5) -0.1469(2) -1.0129(4) 0.106(2) Uani 1 1 d . . .
F8 F -0.3643(5) -0.0965(2) -1.1004(4) 0.0932(17) Uani 1 1 d . . .
F9 F -0.3661(8) -0.1695(3) -0.9557(5) 0.160(3) Uani 1 1 d . . .
F10 F -0.3007(4) 0.17960(19) -0.9287(4) 0.0777(13) Uani 1 1 d . . .
F11 F -0.4874(4) 0.13414(19) -0.9406(3) 0.0716(13) Uani 1 1 d . . .
F12 F -0.3842(3) 0.17298(16) -0.7705(3) 0.0542(10) Uani 1 1 d . . .
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'
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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C1 114.8(5) . . ?
N1 C2 C3 109.7(5) . . ?
C1 C2 C3 111.6(5) . . ?
N1 C2 H2 104(3) . . ?
C1 C2 H2 114(3) . . ?
C3 C2 H2 101(3) . . ?
N2 C3 C9 113.6(5) . . ?
N2 C3 C2 108.1(4) . . ?
C9 C3 C2 110.0(5) . . ?
N2 C3 H3 108.3 . . ?
C9 C3 H3 108.3 . . ?
C2 C3 H3 108.3 . . ?
C5 C4 C9 119.7(7) . . ?
C5 C4 H4 121(4) . . ?
C9 C4 H4 120(4) . . ?
C6 C5 C4 121.1(7) . . ?
C6 C5 H5 122(5) . . ?
C4 C5 H5 116(5) . . ?
C5 C6 C7 120.6(6) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C8 118.6(7) . . ?
C6 C7 H7 130(4) . . ?
C8 C7 H7 111(4) . . ?
C9 C8 C7 121.1(6) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C4 119.0(6) . . ?
C8 C9 C3 121.3(5) . . ?
C4 C9 C3 119.6(6) . . ?
O1 C10 N2 123.3(5) . . ?
O1 C10 N3 121.3(5) . . ?
N2 C10 N3 115.4(4) . . ?
N3 C11 C12 119.0(5) . . ?
N3 C11 C16 123.0(5) . . ?
C12 C11 C16 117.8(5) . . ?
C13 C12 C11 121.8(5) . . ?
C13 C12 H12 125(3) . . ?
C11 C12 H12 113(3) . . ?
C12 C13 C14 120.3(5) . . ?
C12 C13 C18 119.3(5) . . ?
C14 C13 C18 120.3(6) . . ?
C15 C14 C13 118.0(6) . . ?
C15 C14 H14 119(3) . . ?
C13 C14 H14 123(3) . . ?
C16 C15 C14 121.7(5) . . ?
C16 C15 C17 119.8(5) . . ?
C14 C15 C17 118.3(6) . . ?
C15 C16 C11 120.3(5) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
F5 C17 F4 108.6(6) . . ?
F5 C17 F6 105.7(6) . . ?
F4 C17 F6 104.6(6) . . ?
F5 C17 C15 112.2(5) . . ?
F4 C17 C15 112.0(5) . . ?
F6 C17 C15 113.2(5) . . ?
F2 C18 F1 106.0(5) . . ?
F2 C18 F3 106.5(5) . . ?
F1 C18 F3 106.0(5) . . ?
F2 C18 C13 112.3(5) . . ?
F1 C18 C13 112.5(5) . . ?
F3 C18 C13 113.1(5) . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 N1 C20 110.7(5) . . ?
C19 N1 C2 114.7(5) . . ?
C20 N1 C2 112.5(4) . . ?
C10 N2 C3 123.1(4) . . ?
C10 N2 H2N 119(4) . . ?
C3 N2 H2N 113(4) . . ?
C10 N3 C11 128.2(4) . . ?
C10 N3 H3N 113(5) . . ?
C11 N3 H3N 116(5) . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N4 C22 C21 115.2(5) . . ?
N4 C22 C23 109.5(4) . . ?
C21 C22 C23 111.9(4) . . ?
N4 C22 H22 101(3) . . ?
C21 C22 H22 109(3) . . ?
C23 C22 H22 109(3) . . ?
N5 C23 C29 112.2(5) . . ?
N5 C23 C22 106.7(4) . . ?
C29 C23 C22 110.7(5) . . ?
N5 C23 H23 106(3) . . ?
C29 C23 H23 110(3) . . ?
C22 C23 H23 111(3) . . ?
C25 C24 C29 118.9(7) . . ?
C25 C24 H24 126(3) . . ?
C29 C24 H24 115(3) . . ?
C26 C25 C24 122.5(7) . . ?
C26 C25 H25 133(4) . . ?
C24 C25 H25 105(4) . . ?
C25 C26 C27 119.0(7) . . ?
C25 C26 H26 131(3) . . ?
C27 C26 H26 110(3) . . ?
C28 C27 C26 119.5(7) . . ?
C28 C27 H27 122(4) . . ?
C26 C27 H27 118(4) . . ?
C29 C28 C27 122.4(6) . . ?
C29 C28 H28 118.8 . . ?
C27 C28 H28 118.8 . . ?
C28 C29 C24 117.7(6) . . ?
C28 C29 C23 122.3(5) . . ?
C24 C29 C23 119.7(6) . . ?
O2 C30 N5 123.3(5) . . ?
O2 C30 N6 122.1(5) . . ?
N5 C30 N6 114.6(4) . . ?
N6 C31 C32 118.7(5) . . ?
N6 C31 C36 123.9(5) . . ?
C32 C31 C36 117.3(5) . . ?
C33 C32 C31 122.0(5) . . ?
C33 C32 H32 120(3) . . ?
C31 C32 H32 118(3) . . ?
C32 C33 C34 121.2(5) . . ?
C32 C33 C38 119.6(5) . . ?
C34 C33 C38 119.2(5) . . ?
C35 C34 C33 117.2(5) . . ?
C35 C34 H34 124(3) . . ?
C33 C34 H34 119(3) . . ?
C36 C35 C34 122.1(5) . . ?
C36 C35 C37 119.0(5) . . ?
C34 C35 C37 119.0(5) . . ?
C35 C36 C31 120.2(5) . . ?
C35 C36 H36 124(3) . . ?
C31 C36 H36 115(3) . . ?
F12 C37 F11 107.6(5) . . ?
F12 C37 F10 106.3(5) . . ?
F11 C37 F10 106.6(5) . . ?
F12 C37 C35 112.5(5) . . ?
F11 C37 C35 112.9(5) . . ?
F10 C37 C35 110.7(5) . . ?
F9 C38 F8 110.3(7) . . ?
F9 C38 F7 103.8(6) . . ?
F8 C38 F7 104.2(6) . . ?
F9 C38 C33 113.5(6) . . ?
F8 C38 C33 113.6(5) . . ?
F7 C38 C33 110.6(6) . . ?
N4 C39 H39A 109.5 . . ?
N4 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
N4 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
N4 C40 H40A 109.5 . . ?
N4 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
N4 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C39 N4 C40 111.0(5) . . ?
C39 N4 C22 115.1(5) . . ?
C40 N4 C22 113.9(5) . . ?
C30 N5 C23 123.5(4) . . ?
C30 N5 H5N 123(5) . . ?
C23 N5 H5N 110(5) . . ?
C30 N6 C31 129.6(4) . . ?
C30 N6 H6N 111(5) . . ?
C31 N6 H6N 119(5) . . ?
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 C2 1.524(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.478(7) . ?
C2 C3 1.541(8) . ?
C2 H2 0.97(5) . ?
C3 N2 1.444(7) . ?
C3 C9 1.510(8) . ?
C3 H3 0.9800 . ?
C4 C5 1.381(10) . ?
C4 C9 1.412(8) . ?
C4 H4 0.98(7) . ?
C5 C6 1.360(11) . ?
C5 H5 0.93(8) . ?
C6 C7 1.398(11) . ?
C6 H6 0.9300 . ?
C7 C8 1.405(9) . ?
C7 H7 0.93(7) . ?
C8 C9 1.375(8) . ?
C8 H8 0.9300 . ?
C10 O1 1.240(6) . ?
C10 N2 1.345(7) . ?
C10 N3 1.370(7) . ?
C11 N3 1.380(7) . ?
C11 C12 1.385(8) . ?
C11 C16 1.404(7) . ?
C12 C13 1.368(8) . ?
C12 H12 0.93(6) . ?
C13 C14 1.395(8) . ?
C13 C18 1.490(8) . ?
C14 C15 1.392(9) . ?
C14 H14 0.91(6) . ?
C15 C16 1.364(8) . ?
C15 C17 1.517(9) . ?
C16 H16 0.9300 . ?
C17 F5 1.298(7) . ?
C17 F4 1.318(8) . ?
C17 F6 1.325(7) . ?
C18 F2 1.323(7) . ?
C18 F1 1.333(7) . ?
C18 F3 1.337(7) . ?
C19 N1 1.441(7) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 N1 1.448(7) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N2 H2N 0.82(6) . ?
N3 H3N 0.69(6) . ?
C21 C22 1.515(8) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 N4 1.468(7) . ?
C22 C23 1.544(7) . ?
C22 H22 1.02(6) . ?
C23 N5 1.461(7) . ?
C23 C29 1.513(8) . ?
C23 H23 0.93(6) . ?
C24 C25 1.397(10) . ?
C24 C29 1.407(8) . ?
C24 H24 0.98(6) . ?
C25 C26 1.352(10) . ?
C25 H25 0.84(6) . ?
C26 C27 1.385(10) . ?
C26 H26 1.01(6) . ?
C27 C28 1.384(9) . ?
C27 H27 1.10(9) . ?
C28 C29 1.379(8) . ?
C28 H28 0.9300 . ?
C30 O2 1.246(6) . ?
C30 N5 1.338(7) . ?
C30 N6 1.366(7) . ?
C31 N6 1.376(7) . ?
C31 C32 1.396(7) . ?
C31 C36 1.402(7) . ?
C32 C33 1.363(8) . ?
C32 H32 0.95(5) . ?
C33 C34 1.396(8) . ?
C33 C38 1.502(8) . ?
C34 C35 1.391(8) . ?
C34 H34 0.95(6) . ?
C35 C36 1.383(8) . ?
C35 C37 1.510(8) . ?
C36 H36 0.94(5) . ?
C37 F12 1.317(7) . ?
C37 F11 1.322(7) . ?
C37 F10 1.332(7) . ?
C38 F9 1.273(9) . ?
C38 F8 1.297(7) . ?
C38 F7 1.339(8) . ?
C39 N4 1.453(8) . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 N4 1.454(7) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
N5 H5N 0.73(6) . ?
N6 H6N 0.69(6) . ?
