#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:15:31 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178427 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/48/4024867.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_4024867
loop_
_publ_author_name
'Jennifer A. Kozak'
'Jennifer M. Dodd'
'Tyler J. Harrison'
'Katherine J. Jardine'
'Brian O. Patrick'
'Gregory R. Dake'
_publ_section_title
;
Enamides and Enesulfonamides as Nucleophiles: Formation of Complex Ring
Systems through a Platinum(II)-Catalyzed Addition/Friedel-Crafts Pathway
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6929
_journal_page_last               6935
_journal_paper_doi               10.1021/jo901512m
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C18 H18 F3 N O'
_chemical_formula_weight         321.33
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.869(5)
_cell_angle_beta                 106.046(5)
_cell_angle_gamma                97.731(5)
_cell_formula_units_Z            2
_cell_length_a                   9.2986(10)
_cell_length_b                   9.4653(10)
_cell_length_c                   9.7386(10)
_cell_measurement_reflns_used    8125
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.05
_cell_measurement_theta_min      2.36
_cell_volume                     749.55(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'area detector'
_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  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16296
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  .890
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         3595
_refine_ls_number_restraints     33
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0699P)²+0.2737P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1385
_refine_ls_wR_factor_ref         0.1480
_reflns_number_gt                2946
_reflns_number_total             3595
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901512m_si_003.cif
_cod_data_source_block           gd033
_cod_database_code               4024867
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.7808(7) 0.0288(6) 0.4944(5) 0.0454(9) Uani 0.769(4) 1 d P A 1
C2 C 0.8995(3) 0.1862(3) 0.5521(3) 0.0453(6) Uani 0.769(4) 1 d P A 1
H2A H 0.8837 0.2609 0.6430 0.054 Uiso 1 1 calc R A 1
H2B H 1.0047 0.1715 0.5883 0.054 Uiso 1 1 calc R A 1
C3 C 0.89255(18) 0.25766(18) 0.43362(19) 0.0431(4) Uani 1 1 d . A 1
H3A H 0.9513 0.2110 0.3670 0.052 Uiso 1 1 calc R A 1
H3B H 0.9415 0.3705 0.4882 0.052 Uiso 1 1 calc R A 1
C3A C 0.72491(16) 0.23129(17) 0.33162(17) 0.0360(3) Uani 1 1 d . . .
C4 C 0.6386(3) 0.3274(3) 0.4292(4) 0.0422(6) Uani 0.769(4) 1 d P A 1
H4A H 0.5254 0.2842 0.3783 0.051 Uiso 0.769(4) 1 calc PR A 1
H4B H 0.6695 0.3264 0.5346 0.051 Uiso 0.769(4) 1 calc PR A 1
C5 C 0.6847(3) 0.4925(3) 0.4389(5) 0.0489(7) Uani 0.769(4) 1 d P A 1
H5A H 0.6053 0.5487 0.4590 0.059 Uiso 0.769(4) 1 calc PR A 1
H5B H 0.7850 0.5506 0.5234 0.059 Uiso 0.769(4) 1 calc PR A 1
C6 C 0.6970(3) 0.4748(3) 0.2818(4) 0.0481(6) Uani 0.769(4) 1 d P A 1
H6A H 0.7863 0.5537 0.2937 0.058 Uiso 0.769(4) 1 calc PR A 1
H6B H 0.6015 0.4842 0.2129 0.058 Uiso 0.769(4) 1 calc PR A 1
C6A C 0.7202(2) 0.3101(3) 0.2178(3) 0.0420(6) Uani 0.769(4) 1 d P A 1
C7 C 0.7277(2) 0.2353(3) 0.0807(3) 0.0456(6) Uani 0.769(4) 1 d P A 1
H7 H 0.7215 0.2842 0.0094 0.055 Uiso 0.769(4) 1 calc PR A 1
C7A C 0.7458(3) 0.0749(3) 0.0364(4) 0.0371(5) Uani 0.769(4) 1 d P A 1
C8 C 0.7903(3) 0.0091(3) -0.0903(4) 0.0409(6) Uani 0.769(4) 1 d P A 1
H8 H 0.8048 0.0657 -0.1515 0.049 Uiso 0.769(4) 1 calc PR A 1
C9 C 0.8137(3) -0.1364(5) -0.1280(5) 0.0381(9) Uani 0.769(4) 1 d P A 1
H9 H 0.8430 -0.1811 -0.2160 0.046 Uiso 0.769(4) 1 calc PR A 1
C10 C 0.7950(7) -0.2182(4) -0.0393(5) 0.0383(15) Uani 0.769(4) 1 d PD A 1
C11 C 0.7454(5) -0.1562(5) 0.0864(4) 0.0356(8) Uani 0.769(4) 1 d P A 1
H11 H 0.7309 -0.2141 0.1465 0.043 Uiso 0.769(4) 1 calc PR A 1
C11B C 0.6523(3) 0.0619(4) 0.2492(4) 0.0339(7) Uani 0.769(4) 1 d P A 1
H11B H 0.5401 0.0496 0.1957 0.041 Uiso 0.769(4) 1 calc PR A 1
C12 C 0.5378(4) -0.1503(3) 0.3161(4) 0.0512(7) Uani 0.769(4) 1 d P A 1
H12A H 0.5755 -0.2139 0.3724 0.077 Uiso 0.769(4) 1 calc PR A 1
H12B H 0.5028 -0.2121 0.2038 0.077 Uiso 0.769(4) 1 calc PR A 1
H12C H 0.4514 -0.1156 0.3442 0.077 Uiso 0.769(4) 1 calc PR A 1
C13 C 0.8225(3) -0.3753(2) -0.0772(4) 0.0441(8) Uani 0.769(4) 1 d PD A 1
C11A C 0.7177(3) -0.0110(4) 0.1229(3) 0.0325(6) Uani 0.769(4) 1 d P A 1
O1 O 0.7960(6) -0.0442(5) 0.5770(5) 0.0773(10) Uani 0.769(4) 1 d P A 1
N1 N 0.6613(4) -0.0167(3) 0.3571(4) 0.0378(7) Uani 0.769(4) 1 d P A 1
F1 F 0.9015(10) -0.3944(10) 0.0509(6) 0.0528(15) Uani 0.384(2) 1 d PD A 1
F2 F 0.6943(7) -0.4923(9) -0.1503(7) 0.0501(14) Uani 0.384(2) 1 d PD A 1
F3 F 0.9073(7) -0.4070(8) -0.1709(9) 0.0481(13) Uani 0.384(2) 1 d PD A 1
C4' C 0.6111(14) 0.3124(14) 0.3704(13) 0.054(3) Uiso 0.231(4) 1 d P A 2
H4'1 H 0.6038 0.3169 0.4713 0.064 Uiso 0.231(4) 1 calc PR A 2
H4'2 H 0.5078 0.2626 0.2886 0.064 Uiso 0.231(4) 1 calc PR A 2
C5' C 0.6789(13) 0.4803(13) 0.3800(14) 0.051(3) Uiso 0.231(4) 1 d P A 2
H5'1 H 0.6160 0.5504 0.4188 0.061 Uiso 0.231(4) 1 calc PR A 2
H5'2 H 0.7859 0.5222 0.4557 0.061 Uiso 0.231(4) 1 calc PR A 2
C6' C 0.6800(14) 0.4796(15) 0.2273(14) 0.056(3) Uiso 0.231(4) 1 d P A 2
H6'1 H 0.5761 0.4816 0.1667 0.067 Uiso 0.231(4) 1 calc PR A 2
H6'2 H 0.7543 0.5749 0.2453 0.067 Uiso 0.231(4) 1 calc PR A 2
C6A' C 0.7205(7) 0.3493(7) 0.1393(7) 0.0332(16) Uiso 0.231(4) 1 d P A 2
H6A' H 0.7399 0.3499 0.0487 0.040 Uiso 0.231(4) 1 calc PR A 2
C7' C 0.7343(6) 0.2218(7) 0.1734(6) 0.0238(13) Uiso 0.231(4) 1 d P A 2
C7A' C 0.7493(11) 0.0778(8) 0.0836(9) 0.037(3) Uiso 0.231(4) 1 d PG A 2
C8' C 0.8027(11) 0.0350(8) -0.0408(10) 0.043(3) Uiso 0.231(4) 1 d PG A 2
H8' H 0.8295 0.1086 -0.0816 0.052 Uiso 0.231(4) 1 calc PR A 2
C9' C 0.8169(17) -0.1156(10) -0.1054(12) 0.069(7) Uiso 0.231(4) 1 d PGD A 2
H9' H 0.8534 -0.1449 -0.1905 0.082 Uiso 0.231(4) 1 calc PR A 2
C10' C 0.778(2) -0.2234(9) -0.0457(15) 0.038(6) Uiso 0.231(4) 1 d PGD A 2
C11' C 0.7242(17) -0.1806(11) 0.0787(14) 0.042(5) Uiso 0.231(4) 1 d PGD A 2
H11' H 0.6974 -0.2542 0.1195 0.051 Uiso 0.231(4) 1 calc PR A 2
C11C C 0.7100(13) -0.0300(11) 0.1434(10) 0.044(4) Uiso 0.231(4) 1 d PG A 2
C1B' C 0.6519(13) 0.0430(13) 0.2750(13) 0.026(2) Uiso 0.231(4) 1 d P A 2
H1B' H 0.5367 0.0210 0.2306 0.031 Uiso 0.231(4) 1 calc PR A 2
C12' C 0.5635(16) -0.1449(17) 0.3780(16) 0.071(4) Uiso 0.231(4) 1 d P A 2
H12D H 0.5801 -0.1533 0.4784 0.107 Uiso 0.231(4) 1 calc PR A 2
H12E H 0.5681 -0.2419 0.3019 0.107 Uiso 0.231(4) 1 calc PR A 2
H12F H 0.4618 -0.1253 0.3417 0.107 Uiso 0.231(4) 1 calc PR A 2
N1' N 0.6893(14) -0.0107(14) 0.3965(13) 0.032(2) Uiso 0.231(4) 1 d P A 2
C13' C 0.8092(13) -0.3777(12) -0.1007(13) 0.113(9) Uiso 0.231(4) 1 d PD A 2
F1' F 0.8367(13) -0.4332(13) 0.0121(12) 0.100(4) Uiso 0.231(4) 1 d PD A 2
F2' F 0.9244(14) -0.400(2) -0.1570(17) 0.120(7) Uiso 0.231(4) 1 d PD A 2
F3' F 0.6814(9) -0.4807(10) -0.2146(11) 0.083(3) Uiso 0.231(4) 1 d PD A 2
C1' C 0.814(2) 0.054(2) 0.510(3) 0.064(7) Uiso 0.231(4) 1 d P A 2
O1' O 0.804(3) -0.011(2) 0.608(2) 0.111(7) Uiso 0.231(4) 1 d P A 2
C2' C 0.921(2) 0.163(2) 0.509(2) 0.090(6) Uiso 0.231(4) 1 d P A 2
F5 F 0.9370(13) -0.3759(15) 0.0417(12) 0.107(4) Uani 0.384(2) 1 d P A 3
F4 F 0.7036(12) -0.4830(11) -0.0934(11) 0.089(3) Uani 0.384(2) 1 d P A 3
F6 F 0.8699(13) -0.4159(12) -0.1932(11) 0.103(4) Uani 0.384(2) 1 d P A 3
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
O1 C1 N1 123.8(5) . . ?
O1 C1 C2 118.2(5) . . ?
N1 C1 C2 118.0(3) . . ?
C3 C2 C1 115.7(2) . . ?
C3 C2 H2A 108.3 . . ?
C1 C2 H2A 108.3 . . ?
C3 C2 H2B 108.3 . . ?
C1 C2 H2B 108.3 . . ?
H2A C2 H2B 107.4 . . ?
C2 C3 C3A 111.02(15) . . ?
C2 C3 H3A 109.4 . . ?
C3A C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C3A C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C4' C3A C11B 109.8(5) . . ?
C4' C3A C6A 85.2(5) . . ?
C11B C3A C6A 111.64(18) . . ?
C4' C3A C3 128.2(5) . . ?
C11B C3A C3 109.25(17) . . ?
C6A C3A C3 110.16(13) . . ?
C4' C3A C7' 111.4(5) . . ?
C11B C3A C7' 85.0(3) . . ?
C6A C3A C7' 32.1(2) . . ?
C3 C3A C7' 104.7(2) . . ?
C4' C3A C4 19.5(4) . . ?
C11B C3A C4 115.88(17) . . ?
C6A C3A C4 99.37(16) . . ?
C3 C3A C4 110.18(17) . . ?
C7' C3A C4 128.8(3) . . ?
C4' C3A C1B' 108.4(6) . . ?
C11B C3A C1B' 11.4(4) . . ?
C6A C3A C1B' 123.0(4) . . ?
C3 C3A C1B' 103.3(4) . . ?
C7' C3A C1B' 95.9(4) . . ?
C4 C3A C1B' 110.7(4) . . ?
C5 C4 C3A 106.14(19) . . ?
C5 C4 H4A 110.5 . . ?
C3A C4 H4A 110.5 . . ?
C5 C4 H4B 110.5 . . ?
C3A C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
C6 C5 C4 105.6(2) . . ?
C6 C5 H5A 110.6 . . ?
C4 C5 H5A 110.6 . . ?
C6 C5 H5B 110.6 . . ?
C4 C5 H5B 110.6 . . ?
H5A C5 H5B 108.7 . . ?
C5 C6 C6A 103.2(2) . . ?
C5 C6 H6A 111.1 . . ?
C6A C6 H6A 111.1 . . ?
C5 C6 H6B 111.1 . . ?
C6A C6 H6B 111.1 . . ?
H6A C6 H6B 109.1 . . ?
C7 C6A C3A 120.51(19) . . ?
C7 C6A C6 127.3(2) . . ?
C3A C6A C6 112.1(2) . . ?
C6A C7 C7A 120.2(2) . . ?
C6A C7 H7 119.9 . . ?
C7A C7 H7 119.9 . . ?
C8 C7A C11A 119.81(18) . . ?
C8 C7A C7 120.2(3) . . ?
C11A C7A C7 120.0(3) . . ?
C9 C8 C7A 120.5(2) . . ?
C9 C8 H8 119.7 . . ?
C7A C8 H8 119.7 . . ?
C8 C9 C10 120.2(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C11 120.4(3) . . ?
C9 C10 C13 120.8(3) . . ?
C11 C10 C13 118.8(3) . . ?
C11A C11 C10 119.8(3) . . ?
C11A C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
N1 C11B C3A 112.3(2) . . ?
N1 C11B C11A 112.9(3) . . ?
C3A C11B C11A 110.8(2) . . ?
N1 C11B H11B 106.8 . . ?
C3A C11B H11B 106.8 . . ?
C11A C11B H11B 106.8 . . ?
F2 C13 F1 106.2(5) . . ?
F2 C13 F3 104.4(4) . . ?
F1 C13 F3 105.1(4) . . ?
F2 C13 C10 114.9(5) . . ?
F1 C13 C10 111.9(4) . . ?
F3 C13 C10 113.6(3) . . ?
C11 C11A C7A 119.1(2) . . ?
C11 C11A C11B 124.0(3) . . ?
C7A C11A C11B 116.8(2) . . ?
C1 N1 C12 117.8(3) . . ?
C1 N1 C11B 123.6(3) . . ?
C12 N1 C11B 118.6(3) . . ?
C3A C4' C5' 102.1(8) . . ?
C3A C4' H4'1 111.4 . . ?
C5' C4' H4'1 111.4 . . ?
C3A C4' H4'2 111.4 . . ?
C5' C4' H4'2 111.4 . . ?
H4'1 C4' H4'2 109.2 . . ?
C6' C5' C4' 112.8(10) . . ?
C6' C5' H5'1 109.0 . . ?
C4' C5' H5'1 109.0 . . ?
C6' C5' H5'2 109.0 . . ?
C4' C5' H5'2 109.0 . . ?
H5'1 C5' H5'2 107.8 . . ?
C6A' C6' C5' 113.1(10) . . ?
C6A' C6' H6'1 109.0 . . ?
C5' C6' H6'1 109.0 . . ?
C6A' C6' H6'2 109.0 . . ?
C5' C6' H6'2 109.0 . . ?
H6'1 C6' H6'2 107.8 . . ?
C7' C6A' C6' 125.5(7) . . ?
C7' C6A' H6A' 117.3 . . ?
C6' C6A' H6A' 117.3 . . ?
C6A' C7' C7A' 130.1(6) . . ?
C6A' C7' C3A 116.8(5) . . ?
C7A' C7' C3A 113.0(5) . . ?
C8' C7A' C11C 120.0 . . ?
C8' C7A' C7' 130.7(6) . . ?
C11C C7A' C7' 109.2(6) . . ?
C9' C8' C7A' 120.0 . . ?
C9' C8' H8' 120.0 . . ?
C7A' C8' H8' 120.0 . . ?
C8' C9' C10' 120.0 . . ?
C8' C9' H9' 120.0 . . ?
C10' C9' H9' 120.0 . . ?
C11' C10' C9' 120.0 . . ?
C11' C10' C13' 119.1(4) . . ?
C9' C10' C13' 120.5(4) . . ?
C10' C11' C11C 120.0 . . ?
C10' C11' H11' 120.0 . . ?
C11C C11' H11' 120.0 . . ?
C11' C11C C7A' 120.0 . . ?
C11' C11C C1B' 129.9(7) . . ?
C7A' C11C C1B' 110.1(7) . . ?
N1' C1B' C11C 114.9(9) . . ?
N1' C1B' C3A 113.9(9) . . ?
C11C C1B' C3A 103.2(7) . . ?
N1' C1B' H1B' 108.2 . . ?
C11C C1B' H1B' 108.2 . . ?
C3A C1B' H1B' 108.2 . . ?
N1' C12' H12D 109.5 . . ?
N1' C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
N1' C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?
C1' N1' C1B' 120.7(15) . . ?
C1' N1' C12' 125.2(14) . . ?
C1B' N1' C12' 114.1(10) . . ?
F2' C13' F3' 105.0(7) . . ?
F2' C13' F1' 104.2(7) . . ?
F3' C13' F1' 104.5(7) . . ?
F2' C13' C10' 121.1(11) . . ?
F3' C13' C10' 109.4(10) . . ?
F1' C13' C10' 111.3(9) . . ?
N1' C1' O1' 104.8(18) . . ?
N1' C1' C2' 120(2) . . ?
O1' C1' C2' 135(2) . . ?
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 O1 1.219(5) . ?
C1 N1 1.366(6) . ?
C1 C2 1.549(6) . ?
C2 C3 1.515(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C3A 1.533(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A C4' 1.447(12) . ?
C3A C11B 1.485(4) . ?
C3A C6A 1.527(2) . ?
C3A C7' 1.540(6) . ?
C3A C4 1.551(3) . ?
C3A C1B' 1.656(11) . ?
C4 C5 1.527(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.519(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C6A 1.539(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6A C7 1.309(3) . ?
C7 C7A 1.477(3) . ?
C7 H7 0.9500 . ?
C7A C8 1.382(4) . ?
C7A C11A 1.404(5) . ?
C8 C9 1.363(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.370(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.397(3) . ?
C10 C13 1.482(3) . ?
C11 C11A 1.376(4) . ?
C11 H11 0.9500 . ?
C11B N1 1.472(4) . ?
C11B C11A 1.519(4) . ?
C11B H11B 1.0000 . ?
C12 N1 1.445(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 F2 1.339(6) . ?
C13 F1 1.345(6) . ?
C13 F3 1.349(5) . ?
C4' C5' 1.591(17) . ?
C4' H4'1 0.9900 . ?
C4' H4'2 0.9900 . ?
C5' C6' 1.488(13) . ?
C5' H5'1 0.9900 . ?
C5' H5'2 0.9900 . ?
C6' C6A' 1.407(14) . ?
C6' H6'1 0.9900 . ?
C6' H6'2 0.9900 . ?
C6A' C7' 1.369(9) . ?
C6A' H6A' 0.9500 . ?
C7' C7A' 1.397(9) . ?
C7A' C8' 1.3900 . ?
C7A' C11C 1.3900 . ?
C8' C9' 1.3900 . ?
C8' H8' 0.9500 . ?
C9' C10' 1.3900 . ?
C9' H9' 0.9500 . ?
C10' C11' 1.3900 . ?
C10' C13' 1.475(9) . ?
C11' C11C 1.3900 . ?
C11' H11' 0.9500 . ?
C11C C1B' 1.515(12) . ?
C1B' N1' 1.417(12) . ?
C1B' H1B' 1.0000 . ?
C12' N1' 1.530(19) . ?
C12' H12D 0.9800 . ?
C12' H12E 0.9800 . ?
C12' H12F 0.9800 . ?
N1' C1' 1.26(2) . ?
C13' F2' 1.341(8) . ?
C13' F3' 1.348(8) . ?
C13' F1' 1.350(8) . ?
C1' O1' 1.31(3) . ?
C1' C2' 1.33(2) . ?
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 169.5(4) . . . . ?
N1 C1 C2 C3 -13.3(5) . . . . ?
C1 C2 C3 C3A 37.9(3) . . . . ?
C2 C3 C3A C4' 77.5(6) . . . . ?
C2 C3 C3A C11B -59.5(2) . . . . ?
C2 C3 C3A C6A 177.57(18) . . . . ?
C2 C3 C3A C7' -149.2(3) . . . . ?
C2 C3 C3A C4 68.9(2) . . . . ?
C2 C3 C3A C1B' -49.3(4) . . . . ?
C4' C3A C4 C5 -78.7(16) . . . . ?
C11B C3A C4 C5 -154.6(2) . . . . ?
C6A C3A C4 C5 -34.9(3) . . . . ?
C3 C3A C4 C5 80.7(3) . . . . ?
C7' C3A C4 C5 -49.2(4) . . . . ?
C1B' C3A C4 C5 -165.7(4) . . . . ?
C3A C4 C5 C6 36.6(3) . . . . ?
C4 C5 C6 C6A -21.3(3) . . . . ?
C4' C3A C6A C7 -141.3(5) . . . . ?
C11B C3A C6A C7 -32.0(3) . . . . ?
C3 C3A C6A C7 89.6(2) . . . . ?
C7' C3A C6A C7 4.0(4) . . . . ?
C4 C3A C6A C7 -154.7(2) . . . . ?
C1B' C3A C6A C7 -32.4(5) . . . . ?
C4' C3A C6A C6 35.4(5) . . . . ?
C11B C3A C6A C6 144.8(2) . . . . ?
C3 C3A C6A C6 -93.61(19) . . . . ?
C7' C3A C6A C6 -179.3(4) . . . . ?
C4 C3A C6A C6 22.1(2) . . . . ?
C1B' C3A C6A C6 144.4(5) . . . . ?
C5 C6 C6A C7 175.5(2) . . . . ?
C5 C6 C6A C3A -1.1(2) . . . . ?
C3A C6A C7 C7A -1.9(3) . . . . ?
C6 C6A C7 C7A -178.2(2) . . . . ?
C6A C7 C7A C8 -164.5(2) . . . . ?
C6A C7 C7A C11A 15.4(3) . . . . ?
C11A C7A C8 C9 -2.8(3) . . . . ?
C7 C7A C8 C9 177.2(3) . . . . ?
C7A C8 C9 C10 -0.8(4) . . . . ?
C8 C9 C10 C11 2.8(5) . . . . ?
C8 C9 C10 C13 -179.0(4) . . . . ?
C9 C10 C11 C11A -1.1(5) . . . . ?
C13 C10 C11 C11A -179.4(4) . . . . ?
C4' C3A C11B N1 -89.5(5) . . . . ?
C6A C3A C11B N1 177.8(2) . . . . ?
C3 C3A C11B N1 55.7(3) . . . . ?
C7' C3A C11B N1 159.6(3) . . . . ?
C4 C3A C11B N1 -69.4(3) . . . . ?
C1B' C3A C11B N1 -4(2) . . . . ?
C4' C3A C11B C11A 143.2(5) . . . . ?
C6A C3A C11B C11A 50.5(3) . . . . ?
C3 C3A C11B C11A -71.6(3) . . . . ?
C7' C3A C11B C11A 32.3(3) . . . . ?
C4 C3A C11B C11A 163.3(2) . . . . ?
C1B' C3A C11B C11A -131(3) . . . . ?
C9 C10 C13 F2 -101.8(5) . . . . ?
C11 C10 C13 F2 76.5(6) . . . . ?
C9 C10 C13 F1 137.1(6) . . . . ?
C11 C10 C13 F1 -44.6(6) . . . . ?
C9 C10 C13 F3 18.3(7) . . . . ?
C11 C10 C13 F3 -163.4(5) . . . . ?
C10 C11 C11A C7A -2.5(4) . . . . ?
C10 C11 C11A C11B 175.3(3) . . . . ?
C8 C7A C11A C11 4.4(3) . . . . ?
C7 C7A C11A C11 -175.6(3) . . . . ?
C8 C7A C11A C11B -173.5(2) . . . . ?
C7 C7A C11A C11B 6.5(3) . . . . ?
N1 C11B C11A C11 15.9(4) . . . . ?
C3A C11B C11A C11 142.8(3) . . . . ?
N1 C11B C11A C7A -166.3(2) . . . . ?
C3A C11B C11A C7A -39.4(3) . . . . ?
O1 C1 N1 C12 6.7(7) . . . . ?
C2 C1 N1 C12 -170.3(3) . . . . ?
O1 C1 N1 C11B -172.9(4) . . . . ?
C2 C1 N1 C11B 10.1(5) . . . . ?
C3A C11B N1 C1 -32.4(4) . . . . ?
C11A C11B N1 C1 93.7(4) . . . . ?
C3A C11B N1 C12 148.0(2) . . . . ?
C11A C11B N1 C12 -85.9(3) . . . . ?
C11B C3A C4' C5' -154.4(6) . . . . ?
C6A C3A C4' C5' -43.1(6) . . . . ?
C3 C3A C4' C5' 68.9(8) . . . . ?
C7' C3A C4' C5' -62.0(8) . . . . ?
C4 C3A C4' C5' 93.6(17) . . . . ?
C1B' C3A C4' C5' -166.3(7) . . . . ?
C3A C4' C5' C6' 65.5(11) . . . . ?
C4' C5' C6' C6A' -38.9(14) . . . . ?
C5' C6' C6A' C7' 10.0(14) . . . . ?
C6' C6A' C7' C7A' 168.6(9) . . . . ?
C6' C6A' C7' C3A -8.2(10) . . . . ?
C4' C3A C7' C6A' 38.1(7) . . . . ?
C11B C3A C7' C6A' 147.4(5) . . . . ?
C6A C3A C7' C6A' 0.6(3) . . . . ?
C3 C3A C7' C6A' -104.0(4) . . . . ?
C4 C3A C7' C6A' 28.0(6) . . . . ?
C1B' C3A C7' C6A' 150.6(6) . . . . ?
C4' C3A C7' C7A' -139.2(7) . . . . ?
C11B C3A C7' C7A' -29.9(5) . . . . ?
C6A C3A C7' C7A' -176.7(7) . . . . ?
C3 C3A C7' C7A' 78.7(5) . . . . ?
C4 C3A C7' C7A' -149.4(5) . . . . ?
C1B' C3A C7' C7A' -26.7(6) . . . . ?
C6A' C7' C7A' C8' 23.2(12) . . . . ?
C3A C7' C7A' C8' -159.9(7) . . . . ?
C6A' C7' C7A' C11C -161.0(7) . . . . ?
C3A C7' C7A' C11C 15.9(7) . . . . ?
C11C C7A' C8' C9' 0.0 . . . . ?
C7' C7A' C8' C9' 175.5(10) . . . . ?
C7A' C8' C9' C10' 0.0 . . . . ?
C8' C9' C10' C11' 0.0 . . . . ?
C8' C9' C10' C13' -172.8(14) . . . . ?
C9' C10' C11' C11C 0.0 . . . . ?
C13' C10' C11' C11C 172.9(14) . . . . ?
C10' C11' C11C C7A' 0.0 . . . . ?
C10' C11' C11C C1B' 178.4(11) . . . . ?
C8' C7A' C11C C11' 0.0 . . . . ?
C7' C7A' C11C C11' -176.4(8) . . . . ?
C8' C7A' C11C C1B' -178.7(9) . . . . ?
C7' C7A' C11C C1B' 4.9(9) . . . . ?
C11' C11C C1B' N1' 35.4(14) . . . . ?
C7A' C11C C1B' N1' -146.0(9) . . . . ?
C11' C11C C1B' C3A 160.1(7) . . . . ?
C7A' C11C C1B' C3A -21.4(9) . . . . ?
C4' C3A C1B' N1' -92.9(10) . . . . ?
C11B C3A C1B' N1' 168(3) . . . . ?
C6A C3A C1B' N1' 170.7(7) . . . . ?
C3 C3A C1B' N1' 45.5(9) . . . . ?
C7' C3A C1B' N1' 152.2(8) . . . . ?
C4 C3A C1B' N1' -72.4(9) . . . . ?
C4' C3A C1B' C11C 141.8(8) . . . . ?
C11B C3A C1B' C11C 43(2) . . . . ?
C6A C3A C1B' C11C 45.4(8) . . . . ?
C3 C3A C1B' C11C -79.7(7) . . . . ?
C7' C3A C1B' C11C 26.9(7) . . . . ?
C4 C3A C1B' C11C 162.4(6) . . . . ?
C11C C1B' N1' C1' 88.7(18) . . . . ?
C3A C1B' N1' C1' -30.0(19) . . . . ?
C11C C1B' N1' C12' -93.7(12) . . . . ?
C3A C1B' N1' C12' 147.5(9) . . . . ?
C11' C10' C13' F2' -146.1(9) . . . . ?
C9' C10' C13' F2' 26.7(15) . . . . ?
C11' C10' C13' F3' 91.7(10) . . . . ?
C9' C10' C13' F3' -95.4(10) . . . . ?
C11' C10' C13' F1' -23.2(13) . . . . ?
C9' C10' C13' F1' 149.6(8) . . . . ?
C1B' N1' C1' O1' 173.0(15) . . . . ?
C12' N1' C1' O1' -4(3) . . . . ?
C1B' N1' C1' C2' -8(3) . . . . ?
C12' N1' C1' C2' 175.0(16) . . . . ?
