#------------------------------------------------------------------------------
#$Date: 2026-03-18 02:53:11 +0100 (Wed 18 de Mar de 2026) $
#$Revision: 305120 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/10/7161071.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_7161071
loop_
_publ_author_name
'Yakovleva, Elizaveta D.'
'Shelukho, Evgeniya'
'Erokhin, Pavel'
'Ilyushenkova, Valentina'
'Guryeva, Aleksandra S.'
'Logvinenko, Nikita'
'Khrustalev, Victor N.'
'Grigoriev, Mikhail S.'
'Zubkov, Fedor Ivanovich'
'Zaytsev, Vladimir P.'
_publ_section_title
;
 Application of the intramolecular Diels-Alder vinylarene (IMDAV) reaction
 for the synthesis of benzo-and carbocyclofuroisoindolecarboxylic acids
 and its limitations
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D5OB01918D
_journal_year                    2025
_chemical_formula_sum            'C24 H16 D6 F3 N O5 S'
_chemical_formula_weight         499.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2025-10-13 deposited with the CCDC.	2026-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.219(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1549(7)
_cell_length_b                   16.3136(13)
_cell_length_c                   16.7975(14)
_cell_measurement_reflns_used    9002
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.20
_cell_measurement_theta_min      2.74
_cell_volume                     2233.0(3)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            38520
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         4.234
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.735
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 2801 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     622
_refine_ls_number_reflns         14240
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0577P)²+0.9523P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1277
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.896
_reflns_Friedel_fraction_max     0.804
_reflns_number_gt                11435
_reflns_number_total             14240
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ob01918d2.cif
_cod_data_source_block           zv1763
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7161071
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.940
_shelx_estimated_absorpt_t_max   0.984
loop_
_space_group_symop_operation_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_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
F1 F 0.6488(4) 0.4143(2) 0.3012(2) 0.0304(9) Uani 1 1 d . . . . .
F2 F 0.4865(4) 0.5129(2) 0.3324(2) 0.0329(8) Uani 1 1 d . . . . .
F3 F 0.4805(4) 0.3986(2) 0.3953(2) 0.0311(8) Uani 1 1 d . . . . .
O1 O 0.6264(5) 0.6691(3) 0.3962(3) 0.0291(10) Uani 1 1 d . . . . .
O2 O 0.5028(5) 0.5119(3) 0.5136(3) 0.0340(11) Uani 1 1 d . . . . .
O3 O 0.7576(5) 0.5592(3) 0.5385(3) 0.0290(10) Uani 1 1 d . . . . .
H3 H 0.718203 0.577704 0.580309 0.035 Uiso 1 1 calc R U . . .
O5 O 1.0242(5) 0.3305(2) 0.3730(3) 0.0263(10) Uani 1 1 d . . . . .
N2 N 0.9019(6) 0.6877(3) 0.3752(3) 0.0224(11) Uani 1 1 d . . . . .
C1 C 0.7623(7) 0.6432(4) 0.3857(3) 0.0217(13) Uani 1 1 d . . . . .
C3 C 1.0431(7) 0.6362(4) 0.3554(4) 0.0229(13) Uani 1 1 d . . . . .
H3A H 1.147182 0.658178 0.378950 0.027 Uiso 1 1 calc R U . . .
H3B H 1.052512 0.630461 0.297053 0.027 Uiso 1 1 calc R U . . .
C3A C 0.9967(7) 0.5551(4) 0.3939(4) 0.0239(13) Uani 1 1 d . . . . .
H3AA H 1.016402 0.559802 0.452824 0.029 Uiso 1 1 calc R U . . .
C4 C 1.0715(7) 0.4763(4) 0.3664(4) 0.0239(13) Uani 1 1 d . . . . .
H4A H 1.166615 0.473011 0.335563 0.029 Uiso 1 1 calc R U . . .
C4A C 0.9874(7) 0.4118(4) 0.3907(3) 0.0230(13) Uani 1 1 d . . . . .
C5A C 0.9085(7) 0.2818(4) 0.4098(4) 0.0234(13) Uani 1 1 d . . . . .
C6 C 0.9072(8) 0.1980(4) 0.4055(4) 0.0271(14) Uani 1 1 d . . . . .
H6A H 0.986549 0.168462 0.377012 0.033 Uiso 1 1 calc R U . . .
C7 C 0.7824(8) 0.1583(4) 0.4453(4) 0.0275(15) Uani 1 1 d . . . . .
H7A H 0.774562 0.100247 0.443223 0.033 Uiso 1 1 calc R U . . .
C8 C 0.6704(8) 0.2023(4) 0.4877(4) 0.0278(15) Uani 1 1 d . . . . .
H8A H 0.587799 0.173597 0.514745 0.033 Uiso 1 1 calc R U . . .
C9 C 0.6750(7) 0.2880(4) 0.4920(4) 0.0246(14) Uani 1 1 d . . . . .
H9A H 0.598804 0.317657 0.522150 0.029 Uiso 1 1 calc R U . . .
C9A C 0.7950(7) 0.3278(4) 0.4505(4) 0.0216(13) Uani 1 1 d . . . . .
C9B C 0.8442(7) 0.4171(4) 0.4452(4) 0.0231(13) Uani 1 1 d . . . . .
H9BA H 0.891151 0.432637 0.498951 0.028 Uiso 1 1 calc R U . . .
C10 C 0.7156(7) 0.4859(4) 0.4205(4) 0.0231(13) Uani 1 1 d . . . . .
C10A C 0.8110(7) 0.5532(4) 0.3756(4) 0.0215(13) Uani 1 1 d . . . . .
H10A H 0.795945 0.540573 0.317515 0.026 Uiso 1 1 calc R U . . .
C11 C 0.6423(7) 0.5211(4) 0.4962(4) 0.0256(14) Uani 1 1 d . . . . .
C12 C 0.5832(7) 0.4524(4) 0.3632(4) 0.0271(14) Uani 1 1 d . . . . .
C13 C 0.9071(7) 0.7744(4) 0.3723(4) 0.0224(13) Uani 1 1 d . . . . .
C14 C 0.8134(8) 0.8208(4) 0.4228(4) 0.0315(15) Uani 1 1 d . . . . .
H14A H 0.747073 0.794422 0.460372 0.038 Uiso 1 1 calc R U . . .
C15 C 0.8167(7) 0.9067(4) 0.4181(4) 0.0265(14) Uani 1 1 d . . . . .
H15A H 0.750931 0.938584 0.451831 0.032 Uiso 1 1 calc R U . . .
C16 C 0.9157(8) 0.9446(4) 0.3646(4) 0.0309(15) Uani 1 1 d . . . . .
H16A H 0.917753 1.002755 0.361134 0.037 Uiso 1 1 calc R U . . .
C17 C 1.0115(8) 0.8982(4) 0.3162(4) 0.0315(15) Uani 1 1 d . . . . .
H17A H 1.082166 0.924934 0.280725 0.038 Uiso 1 1 calc R U . . .
C18 C 1.0070(7) 0.8134(4) 0.3181(4) 0.0268(14) Uani 1 1 d . . . . .
H18A H 1.070838 0.782145 0.283024 0.032 Uiso 1 1 calc R U . . .
F21 F 0.6575(5) 0.5880(3) 0.1890(2) 0.0455(11) Uani 1 1 d . . . . .
F22 F 0.4974(4) 0.4884(3) 0.1495(2) 0.0454(11) Uani 1 1 d . . . . .
F23 F 0.4943(4) 0.6020(2) 0.0859(2) 0.0398(10) Uani 1 1 d . . . . .
O21 O 0.6377(5) 0.3318(3) 0.0921(3) 0.0365(12) Uani 1 1 d . . . . .
O22 O 0.5208(6) 0.4844(3) -0.0281(3) 0.0387(12) Uani 1 1 d . . . . .
O23 O 0.7814(5) 0.4447(3) -0.0442(3) 0.0335(11) Uani 1 1 d . . . . .
H23 H 0.742564 0.425305 -0.087255 0.040 Uiso 1 1 calc R U . . .
O25 O 1.0419(6) 0.6697(3) 0.1357(3) 0.0325(11) Uani 1 1 d . . . . .
N22 N 0.9123(6) 0.3125(3) 0.1289(3) 0.0297(13) Uani 1 1 d . . . . .
C21 C 0.7725(9) 0.3584(4) 0.1106(4) 0.0307(16) Uani 1 1 d . . . . .
C23 C 1.0510(8) 0.3635(4) 0.1560(4) 0.0277(14) Uani 1 1 d . . . . .
H23A H 1.156358 0.340865 0.138398 0.033 Uiso 1 1 calc R U . . .
H23B H 1.055997 0.369331 0.214666 0.033 Uiso 1 1 calc R U . . .
C23A C 1.0102(7) 0.4446(4) 0.1150(4) 0.0276(15) Uani 1 1 d . . . . .
H23C H 1.033618 0.439470 0.057197 0.033 Uiso 1 1 calc R U . . .
C24 C 1.0826(7) 0.5232(4) 0.1457(4) 0.0278(14) Uani 1 1 d . . . . .
H24A H 1.174744 0.526221 0.181978 0.033 Uiso 1 1 calc R U . . .
C24A C 1.0035(8) 0.5879(4) 0.1167(4) 0.0293(15) Uani 1 1 d . . . . .
C25A C 0.9266(8) 0.7176(4) 0.0944(4) 0.0320(16) Uani 1 1 d . . . . .
C26 C 0.9269(9) 0.8025(4) 0.0986(4) 0.0367(17) Uani 1 1 d . . . . .
H26A H 1.003999 0.831470 0.131733 0.044 Uiso 1 1 calc R U . . .
C27 C 0.8093(9) 0.8424(4) 0.0520(4) 0.0383(18) Uani 1 1 d . . . . .
H27A H 0.807097 0.900654 0.051696 0.046 Uiso 1 1 calc R U . . .
C28 C 0.6942(8) 0.7997(4) 0.0056(4) 0.0320(16) Uani 1 1 d . . . . .
H28A H 0.612601 0.828949 -0.024672 0.038 Uiso 1 1 calc R U . . .
C29 C 0.6968(8) 0.7148(4) 0.0029(4) 0.0334(16) Uani 1 1 d . . . . .
H29A H 0.618907 0.685294 -0.029373 0.040 Uiso 1 1 calc R U . . .
C29A C 0.8153(8) 0.6746(4) 0.0482(4) 0.0273(14) Uani 1 1 d . . . . .
C29B C 0.8604(8) 0.5842(4) 0.0569(4) 0.0311(16) Uani 1 1 d . . . . .
H29B H 0.908348 0.568316 0.005244 0.037 Uiso 1 1 calc R U . . .
C30 C 0.7315(7) 0.5153(4) 0.0751(4) 0.0259(14) Uani 1 1 d . . . . .
C30A C 0.8229(7) 0.4466(4) 0.1235(4) 0.0250(14) Uani 1 1 d . . . . .
H30A H 0.804894 0.458651 0.180930 0.030 Uiso 1 1 calc R U . . .
C31 C 0.6617(8) 0.4794(4) -0.0044(4) 0.0259(14) Uani 1 1 d . . . . .
C32 C 0.5916(8) 0.5479(5) 0.1233(4) 0.0362(17) Uani 1 1 d . . . . .
C33 C 0.9113(7) 0.2263(4) 0.1333(4) 0.0255(14) Uani 1 1 d . . . . .
C34 C 0.8212(8) 0.1790(5) 0.0779(4) 0.0340(16) Uani 1 1 d . . . . .
H34A H 0.759757 0.204907 0.035816 0.041 Uiso 1 1 calc R U . . .
C35 C 0.8212(7) 0.0947(4) 0.0842(4) 0.0307(15) Uani 1 1 d . . . . .
H35A H 0.758720 0.062781 0.046711 0.037 Uiso 1 1 calc R U . . .
C36 C 0.9122(8) 0.0562(4) 0.1451(4) 0.0337(16) Uani 1 1 d . . . . .
H36A H 0.911733 -0.001851 0.149331 0.040 Uiso 1 1 calc R U . . .
C37 C 1.0025(8) 0.1024(4) 0.1991(4) 0.0322(16) Uani 1 1 d . . . . .
H37A H 1.064377 0.075951 0.240788 0.039 Uiso 1 1 calc R U . . .
C38 C 1.0046(8) 0.1871(4) 0.1937(4) 0.0296(15) Uani 1 1 d . . . . .
H38A H 1.069124 0.218479 0.230833 0.036 Uiso 1 1 calc R U . . .
S1 S 0.5166(2) 0.61998(11) 0.70843(9) 0.0330(4) Uani 1 1 d . . . . .
O41 O 0.6821(5) 0.6250(3) 0.6696(2) 0.0338(11) Uani 1 1 d . . . . .
C41 C 0.5671(9) 0.5911(6) 0.8092(5) 0.052(2) Uani 1 1 d . . . . .
D41A D 0.466236 0.586479 0.838812 0.077 Uiso 1 1 calc R U . . .
D41B D 0.624076 0.538237 0.809866 0.077 Uiso 1 1 calc R U . . .
D41C D 0.638512 0.632878 0.834209 0.077 Uiso 1 1 calc R U . . .
C42 C 0.4605(10) 0.7235(5) 0.7269(5) 0.052(2) Uani 1 1 d . . . . .
D42A D 0.354158 0.724741 0.752150 0.078 Uiso 1 1 calc R U . . .
D42B D 0.543914 0.749066 0.762402 0.078 Uiso 1 1 calc R U . . .
D42C D 0.452570 0.753592 0.676460 0.078 Uiso 1 1 calc R U . . .
S2A S 0.5556(3) 0.3186(2) -0.17500(18) 0.0413(12) Uani 0.651(7) 1 d . . P A 1
O42 O 0.6994(5) 0.3796(3) -0.1776(3) 0.0397(12) Uani 1 1 d . . . . .
C43 C 0.3958(17) 0.3740(8) -0.2270(8) 0.050(3) Uiso 0.651(7) 1 d . . P A 1
D43A D 0.295483 0.340899 -0.229403 0.076 Uiso 0.651(7) 1 calc R U P A 1
D43B D 0.375211 0.425445 -0.198942 0.076 Uiso 0.651(7) 1 calc R U P A 1
D43C D 0.429058 0.386108 -0.281206 0.076 Uiso 0.651(7) 1 calc R U P A 1
C44 C 0.5947(15) 0.2414(7) -0.2463(7) 0.046(3) Uiso 0.651(7) 1 d . . P A 1
D44A D 0.505910 0.200901 -0.246897 0.068 Uiso 0.651(7) 1 calc R U P A 1
D44B D 0.600604 0.266361 -0.299198 0.068 Uiso 0.651(7) 1 calc R U P A 1
D44C D 0.699106 0.214353 -0.232215 0.068 Uiso 0.651(7) 1 calc R U P A 1
S2B S 0.5253(11) 0.3724(4) -0.2152(4) 0.067(3) Uani 0.349(7) 1 d . . P A 2
C45 C 0.546(3) 0.3877(19) -0.3157(17) 0.072(8) Uiso 0.349(7) 1 d . . P A 2
D45A D 0.438182 0.383864 -0.343269 0.108 Uiso 0.349(7) 1 calc R U P A 2
D45B D 0.592747 0.442155 -0.324564 0.108 Uiso 0.349(7) 1 calc R U P A 2
D45C D 0.619049 0.345793 -0.336551 0.108 Uiso 0.349(7) 1 calc R U P A 2
C46 C 0.492(4) 0.266(2) -0.211(2) 0.098(11) Uiso 0.349(7) 1 d . . P A 2
D46A D 0.382113 0.253621 -0.233471 0.147 Uiso 0.349(7) 1 calc R U P A 2
D46B D 0.574545 0.237813 -0.241095 0.147 Uiso 0.349(7) 1 calc R U P A 2
D46C D 0.499474 0.248245 -0.155054 0.147 Uiso 0.349(7) 1 calc R U P A 2
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'
D D 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'
S S 0.1246 0.1234 '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
C11 O3 H3 109.5 . . ?
C4A O5 C5A 107.0(4) . . ?
C1 N2 C13 124.1(5) . . ?
C1 N2 C3 112.8(5) . . ?
C13 N2 C3 122.5(5) . . ?
O1 C1 N2 127.4(6) . . ?
O1 C1 C10A 126.6(5) . . ?
N2 C1 C10A 105.9(5) . . ?
N2 C3 C3A 101.0(4) . . ?
N2 C3 H3A 111.6 . . ?
C3A C3 H3A 111.6 . . ?
N2 C3 H3B 111.6 . . ?
C3A C3 H3B 111.6 . . ?
H3A C3 H3B 109.4 . . ?
C4 C3A C3 120.0(5) . . ?
C4 C3A C10A 109.3(5) . . ?
C3 C3A C10A 101.0(5) . . ?
C4 C3A H3AA 108.6 . . ?
C3 C3A H3AA 108.6 . . ?
C10A C3A H3AA 108.6 . . ?
C4A C4 C3A 111.2(5) . . ?
C4A C4 H4A 124.4 . . ?
C3A C4 H4A 124.4 . . ?
C4 C4A O5 124.7(5) . . ?
C4 C4A C9B 124.1(5) . . ?
O5 C4A C9B 111.1(5) . . ?
C6 C5A C9A 124.1(6) . . ?
C6 C5A O5 123.2(5) . . ?
C9A C5A O5 112.7(5) . . ?
C5A C6 C7 116.1(6) . . ?
C5A C6 H6A 121.9 . . ?
C7 C6 H6A 121.9 . . ?
C8 C7 C6 121.0(6) . . ?
C8 C7 H7A 119.5 . . ?
C6 C7 H7A 119.5 . . ?
C7 C8 C9 121.9(6) . . ?
C7 C8 H8A 119.1 . . ?
C9 C8 H8A 119.1 . . ?
C9A C9 C8 117.4(6) . . ?
C9A C9 H9A 121.3 . . ?
C8 C9 H9A 121.3 . . ?
C9 C9A C5A 119.4(6) . . ?
C9 C9A C9B 132.5(5) . . ?
C5A C9A C9B 107.8(5) . . ?
C4A C9B C9A 101.2(5) . . ?
C4A C9B C10 113.7(5) . . ?
C9A C9B C10 121.6(5) . . ?
C4A C9B H9BA 106.5 . . ?
C9A C9B H9BA 106.5 . . ?
C10 C9B H9BA 106.5 . . ?
C12 C10 C11 111.6(5) . . ?
C12 C10 C10A 107.7(5) . . ?
C11 C10 C10A 110.8(5) . . ?
C12 C10 C9B 111.0(5) . . ?
C11 C10 C9B 108.9(5) . . ?
C10A C10 C9B 106.8(4) . . ?
C1 C10A C3A 102.5(5) . . ?
C1 C10A C10 119.0(5) . . ?
C3A C10A C10 115.2(5) . . ?
C1 C10A H10A 106.4 . . ?
C3A C10A H10A 106.4 . . ?
C10 C10A H10A 106.4 . . ?
O2 C11 O3 126.5(6) . . ?
O2 C11 C10 124.1(6) . . ?
O3 C11 C10 109.3(5) . . ?
F3 C12 F1 106.4(5) . . ?
F3 C12 F2 105.5(5) . . ?
F1 C12 F2 106.5(5) . . ?
F3 C12 C10 114.9(5) . . ?
F1 C12 C10 111.3(5) . . ?
F2 C12 C10 111.6(5) . . ?
C14 C13 C18 119.9(6) . . ?
C14 C13 N2 120.4(5) . . ?
C18 C13 N2 119.7(5) . . ?
C13 C14 C15 119.9(6) . . ?
C13 C14 H14A 120.1 . . ?
C15 C14 H14A 120.1 . . ?
C16 C15 C14 119.8(6) . . ?
C16 C15 H15A 120.1 . . ?
C14 C15 H15A 120.1 . . ?
C17 C16 C15 119.9(6) . . ?
C17 C16 H16A 120.0 . . ?
C15 C16 H16A 120.0 . . ?
C16 C17 C18 121.3(6) . . ?
C16 C17 H17A 119.4 . . ?
C18 C17 H17A 119.4 . . ?
C17 C18 C13 119.1(6) . . ?
C17 C18 H18A 120.4 . . ?
C13 C18 H18A 120.4 . . ?
C31 O23 H23 109.5 . . ?
C25A O25 C24A 106.3(5) . . ?
C21 N22 C33 123.0(6) . . ?
C21 N22 C23 112.4(6) . . ?
C33 N22 C23 123.9(5) . . ?
O21 C21 N22 126.4(7) . . ?
O21 C21 C30A 128.1(6) . . ?
N22 C21 C30A 105.4(6) . . ?
N22 C23 C23A 101.6(5) . . ?
N22 C23 H23A 111.5 . . ?
C23A C23 H23A 111.5 . . ?
N22 C23 H23B 111.5 . . ?
C23A C23 H23B 111.5 . . ?
H23A C23 H23B 109.3 . . ?
C24 C23A C23 120.9(5) . . ?
C24 C23A C30A 109.2(5) . . ?
C23 C23A C30A 100.2(5) . . ?
C24 C23A H23C 108.6 . . ?
C23 C23A H23C 108.6 . . ?
C30A C23A H23C 108.6 . . ?
C24A C24 C23A 112.2(6) . . ?
C24A C24 H24A 123.9 . . ?
C23A C24 H24A 123.9 . . ?
C24 C24A O25 125.1(6) . . ?
C24 C24A C29B 124.6(6) . . ?
O25 C24A C29B 110.4(5) . . ?
C29A C25A C26 122.9(6) . . ?
C29A C25A O25 114.6(6) . . ?
C26 C25A O25 122.5(6) . . ?
C27 C26 C25A 116.3(6) . . ?
C27 C26 H26A 121.8 . . ?
C25A C26 H26A 121.8 . . ?
C26 C27 C28 121.5(6) . . ?
C26 C27 H27A 119.2 . . ?
C28 C27 H27A 119.2 . . ?
C27 C28 C29 120.7(6) . . ?
C27 C28 H28A 119.7 . . ?
C29 C28 H28A 119.7 . . ?
C29A C29 C28 118.1(6) . . ?
C29A C29 H29A 121.0 . . ?
C28 C29 H29A 121.0 . . ?
C25A C29A C29 120.5(6) . . ?
C25A C29A C29B 106.9(6) . . ?
C29 C29A C29B 132.6(6) . . ?
C24A C29B C29A 101.7(5) . . ?
C24A C29B C30 113.8(5) . . ?
C29A C29B C30 123.2(6) . . ?
C24A C29B H29B 105.6 . . ?
C29A C29B H29B 105.6 . . ?
C30 C29B H29B 105.6 . . ?
C32 C30 C31 109.5(5) . . ?
C32 C30 C30A 109.1(5) . . ?
C31 C30 C30A 109.3(5) . . ?
C32 C30 C29B 111.9(6) . . ?
C31 C30 C29B 109.1(5) . . ?
C30A C30 C29B 107.8(5) . . ?
C21 C30A C23A 103.4(5) . . ?
C21 C30A C30 119.2(5) . . ?
C23A C30A C30 115.0(5) . . ?
C21 C30A H30A 106.1 . . ?
C23A C30A H30A 106.1 . . ?
C30 C30A H30A 106.1 . . ?
O22 C31 O23 124.9(6) . . ?
O22 C31 C30 125.0(6) . . ?
O23 C31 C30 110.0(5) . . ?
F22 C32 F23 107.5(5) . . ?
F22 C32 F21 107.2(6) . . ?
F23 C32 F21 105.8(6) . . ?
F22 C32 C30 112.2(6) . . ?
F23 C32 C30 115.3(6) . . ?
F21 C32 C30 108.4(5) . . ?
C34 C33 C38 119.2(6) . . ?
C34 C33 N22 121.5(6) . . ?
C38 C33 N22 119.3(6) . . ?
C35 C34 C33 120.1(6) . . ?
C35 C34 H34A 119.9 . . ?
C33 C34 H34A 119.9 . . ?
C34 C35 C36 120.3(6) . . ?
C34 C35 H35A 119.8 . . ?
C36 C35 H35A 119.8 . . ?
C37 C36 C35 119.8(6) . . ?
C37 C36 H36A 120.1 . . ?
C35 C36 H36A 120.1 . . ?
C36 C37 C38 120.8(6) . . ?
C36 C37 H37A 119.6 . . ?
C38 C37 H37A 119.6 . . ?
C37 C38 C33 119.7(6) . . ?
C37 C38 H38A 120.1 . . ?
C33 C38 H38A 120.1 . . ?
O41 S1 C42 105.2(3) . . ?
O41 S1 C41 104.2(3) . . ?
C42 S1 C41 97.8(4) . . ?
S1 C41 D41A 109.5 . . ?
S1 C41 D41B 109.5 . . ?
D41A C41 D41B 109.5 . . ?
S1 C41 D41C 109.5 . . ?
D41A C41 D41C 109.5 . . ?
D41B C41 D41C 109.5 . . ?
S1 C42 D42A 109.5 . . ?
S1 C42 D42B 109.5 . . ?
D42A C42 D42B 109.5 . . ?
S1 C42 D42C 109.5 . . ?
D42A C42 D42C 109.5 . . ?
D42B C42 D42C 109.5 . . ?
O42 S2A C44 106.4(5) . . ?
O42 S2A C43 101.6(5) . . ?
C44 S2A C43 100.1(6) . . ?
S2A C43 D43A 109.5 . . ?
S2A C43 D43B 109.5 . . ?
D43A C43 D43B 109.5 . . ?
S2A C43 D43C 109.5 . . ?
D43A C43 D43C 109.5 . . ?
D43B C43 D43C 109.5 . . ?
S2A C44 D44A 109.5 . . ?
S2A C44 D44B 109.5 . . ?
D44A C44 D44B 109.5 . . ?
S2A C44 D44C 109.5 . . ?
D44A C44 D44C 109.5 . . ?
D44B C44 D44C 109.5 . . ?
O42 S2B C45 105.6(10) . . ?
O42 S2B C46 101.6(12) . . ?
C45 S2B C46 101.9(17) . . ?
S2B C45 D45A 109.5 . . ?
S2B C45 D45B 109.5 . . ?
D45A C45 D45B 109.5 . . ?
S2B C45 D45C 109.5 . . ?
D45A C45 D45C 109.5 . . ?
D45B C45 D45C 109.5 . . ?
S2B C46 D46A 109.5 . . ?
S2B C46 D46B 109.5 . . ?
D46A C46 D46B 109.5 . . ?
S2B C46 D46C 109.5 . . ?
D46A C46 D46C 109.5 . . ?
D46B C46 D46C 109.5 . . ?
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
F1 C12 1.341(7) . ?
F2 C12 1.354(7) . ?
F3 C12 1.340(7) . ?
O1 C1 1.206(6) . ?
O2 C11 1.195(6) . ?
O3 C11 1.313(8) . ?
O3 H3 0.8400 . ?
O5 C4A 1.395(7) . ?
O5 C5A 1.396(7) . ?
N2 C1 1.367(7) . ?
N2 C13 1.416(8) . ?
N2 C3 1.474(7) . ?
C1 C10A 1.532(8) . ?
C3 C3A 1.527(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A C4 1.503(8) . ?
C3A C10A 1.534(8) . ?
C3A H3AA 1.0000 . ?
C4 C4A 1.329(8) . ?
C4 H4A 0.9500 . ?
C4A C9B 1.513(8) . ?
C5A C6 1.370(9) . ?
C5A C9A 1.391(8) . ?
C6 C7 1.398(9) . ?
C6 H6A 0.9500 . ?
C7 C8 1.381(9) . ?
C7 H7A 0.9500 . ?
C8 C9 1.400(9) . ?
C8 H8A 0.9500 . ?
C9 C9A 1.384(9) . ?
C9 H9A 0.9500 . ?
C9A C9B 1.515(8) . ?
C9B C10 1.581(8) . ?
C9B H9BA 1.0000 . ?
C10 C12 1.520(9) . ?
C10 C11 1.537(9) . ?
C10 C10A 1.557(8) . ?
C10A H10A 1.0000 . ?
C13 C14 1.387(9) . ?
C13 C18 1.398(8) . ?
C14 C15 1.404(9) . ?
C14 H14A 0.9500 . ?
C15 C16 1.378(9) . ?
C15 H15A 0.9500 . ?
C16 C17 1.377(9) . ?
C16 H16A 0.9500 . ?
C17 C18 1.384(9) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
F21 C32 1.374(8) . ?
F22 C32 1.324(8) . ?
F23 C32 1.328(7) . ?
O21 C21 1.211(7) . ?
O22 C31 1.204(7) . ?
O23 C31 1.330(7) . ?
O23 H23 0.8400 . ?
O25 C25A 1.387(8) . ?
O25 C24A 1.405(8) . ?
N22 C21 1.388(8) . ?
N22 C33 1.408(8) . ?
N22 C23 1.462(8) . ?
C21 C30A 1.510(9) . ?
C23 C23A 1.523(9) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23A C24 1.495(9) . ?
C23A C30A 1.541(8) . ?
C23A H23C 1.0000 . ?
C24 C24A 1.321(9) . ?
C24 H24A 0.9500 . ?
C24A C29B 1.511(9) . ?
C25A C29A 1.365(9) . ?
C25A C26 1.386(9) . ?
C26 C27 1.378(10) . ?
C26 H26A 0.9500 . ?
C27 C28 1.384(9) . ?
C27 H27A 0.9500 . ?
C28 C29 1.387(9) . ?
C28 H28A 0.9500 . ?
C29 C29A 1.374(9) . ?
C29 H29A 0.9500 . ?
C29A C29B 1.525(9) . ?
C29B C30 1.578(9) . ?
C29B H29B 1.0000 . ?
C30 C32 1.520(9) . ?
C30 C31 1.547(9) . ?
C30 C30A 1.557(9) . ?
C30A H30A 1.0000 . ?
C33 C34 1.395(9) . ?
C33 C38 1.400(9) . ?
C34 C35 1.379(10) . ?
C34 H34A 0.9500 . ?
C35 C36 1.390(9) . ?
C35 H35A 0.9500 . ?
C36 C37 1.372(9) . ?
C36 H36A 0.9500 . ?
C37 C38 1.385(9) . ?
C37 H37A 0.9500 . ?
C38 H38A 0.9500 . ?
S1 O41 1.524(4) . ?
S1 C42 1.780(7) . ?
S1 C41 1.790(8) . ?
C41 D41A 0.9800 . ?
C41 D41B 0.9800 . ?
C41 D41C 0.9800 . ?
C42 D42A 0.9800 . ?
C42 D42B 0.9800 . ?
C42 D42C 0.9800 . ?
S2A O42 1.540(6) . ?
S2A C44 1.776(12) . ?
S2A C43 1.786(14) . ?
O42 S2B 1.536(8) . ?
C43 D43A 0.9800 . ?
C43 D43B 0.9800 . ?
C43 D43C 0.9800 . ?
C44 D44A 0.9800 . ?
C44 D44B 0.9800 . ?
C44 D44C 0.9800 . ?
S2B C45 1.72(3) . ?
S2B C46 1.76(4) . ?
C45 D45A 0.9800 . ?
C45 D45B 0.9800 . ?
C45 D45C 0.9800 . ?
C46 D46A 0.9800 . ?
C46 D46B 0.9800 . ?
C46 D46C 0.9800 . ?
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
_geom_hbond_publ_flag
O3 H3 O41 0.84 1.72 2.546(6) 166.7 . yes
O23 H23 O42 0.84 1.71 2.545(6) 169.4 . yes
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 N2 C1 O1 -2.2(9) . . . . ?
C3 N2 C1 O1 -173.9(6) . . . . ?
C13 N2 C1 C10A 173.9(5) . . . . ?
C3 N2 C1 C10A 2.3(6) . . . . ?
C1 N2 C3 C3A -26.5(6) . . . . ?
C13 N2 C3 C3A 161.7(5) . . . . ?
N2 C3 C3A C4 158.7(5) . . . . ?
N2 C3 C3A C10A 38.5(6) . . . . ?
C3 C3A C4 C4A -163.7(6) . . . . ?
C10A C3A C4 C4A -47.8(7) . . . . ?
C3A C4 C4A O5 178.4(5) . . . . ?
C3A C4 C4A C9B -5.1(8) . . . . ?
C5A O5 C4A C4 179.6(6) . . . . ?
C5A O5 C4A C9B 2.7(6) . . . . ?
C4A O5 C5A C6 -179.8(6) . . . . ?
C4A O5 C5A C9A 0.7(7) . . . . ?
C9A C5A C6 C7 -0.2(10) . . . . ?
O5 C5A C6 C7 -179.7(5) . . . . ?
C5A C6 C7 C8 -1.3(9) . . . . ?
C6 C7 C8 C9 0.8(10) . . . . ?
C7 C8 C9 C9A 1.3(10) . . . . ?
C8 C9 C9A C5A -2.7(9) . . . . ?
C8 C9 C9A C9B -175.5(6) . . . . ?
C6 C5A C9A C9 2.3(10) . . . . ?
O5 C5A C9A C9 -178.2(5) . . . . ?
C6 C5A C9A C9B 176.7(6) . . . . ?
O5 C5A C9A C9B -3.8(7) . . . . ?
C4 C4A C9B C9A 178.5(6) . . . . ?
O5 C4A C9B C9A -4.7(6) . . . . ?
C4 C4A C9B C10 46.5(8) . . . . ?
O5 C4A C9B C10 -136.7(5) . . . . ?
C9 C9A C9B C4A 178.3(7) . . . . ?
C5A C9A C9B C4A 4.9(6) . . . . ?
C9 C9A C9B C10 -54.7(10) . . . . ?
C5A C9A C9B C10 131.9(6) . . . . ?
C4A C9B C10 C12 89.9(6) . . . . ?
C9A C9B C10 C12 -31.3(7) . . . . ?
C4A C9B C10 C11 -146.8(5) . . . . ?
C9A C9B C10 C11 92.0(7) . . . . ?
C4A C9B C10 C10A -27.1(7) . . . . ?
C9A C9B C10 C10A -148.3(5) . . . . ?
O1 C1 C10A C3A -160.9(6) . . . . ?
N2 C1 C10A C3A 22.9(6) . . . . ?
O1 C1 C10A C10 -32.5(9) . . . . ?
N2 C1 C10A C10 151.4(5) . . . . ?
C4 C3A C10A C1 -165.4(5) . . . . ?
C3 C3A C10A C1 -37.9(6) . . . . ?
C4 C3A C10A C10 63.7(7) . . . . ?
C3 C3A C10A C10 -168.8(5) . . . . ?
C12 C10 C10A C1 96.0(6) . . . . ?
C11 C10 C10A C1 -26.3(7) . . . . ?
C9B C10 C10A C1 -144.8(5) . . . . ?
C12 C10 C10A C3A -141.7(5) . . . . ?
C11 C10 C10A C3A 96.0(6) . . . . ?
C9B C10 C10A C3A -22.4(7) . . . . ?
C12 C10 C11 O2 10.9(8) . . . . ?
C10A C10 C11 O2 130.9(6) . . . . ?
C9B C10 C11 O2 -112.0(6) . . . . ?
C12 C10 C11 O3 -171.4(5) . . . . ?
C10A C10 C11 O3 -51.4(6) . . . . ?
C9B C10 C11 O3 65.7(6) . . . . ?
C11 C10 C12 F3 -52.6(7) . . . . ?
C10A C10 C12 F3 -174.4(5) . . . . ?
C9B C10 C12 F3 69.1(6) . . . . ?
C11 C10 C12 F1 -173.7(5) . . . . ?
C10A C10 C12 F1 64.5(6) . . . . ?
C9B C10 C12 F1 -52.0(6) . . . . ?
C11 C10 C12 F2 67.5(6) . . . . ?
C10A C10 C12 F2 -54.3(6) . . . . ?
C9B C10 C12 F2 -170.8(5) . . . . ?
C1 N2 C13 C14 39.1(9) . . . . ?
C3 N2 C13 C14 -150.1(6) . . . . ?
C1 N2 C13 C18 -140.7(6) . . . . ?
C3 N2 C13 C18 30.2(8) . . . . ?
C18 C13 C14 C15 1.2(10) . . . . ?
N2 C13 C14 C15 -178.5(5) . . . . ?
C13 C14 C15 C16 -1.3(10) . . . . ?
C14 C15 C16 C17 -0.3(10) . . . . ?
C15 C16 C17 C18 2.1(10) . . . . ?
C16 C17 C18 C13 -2.2(10) . . . . ?
C14 C13 C18 C17 0.5(9) . . . . ?
N2 C13 C18 C17 -179.7(5) . . . . ?
C33 N22 C21 O21 -4.2(11) . . . . ?
C23 N22 C21 O21 -174.6(6) . . . . ?
C33 N22 C21 C30A 172.3(6) . . . . ?
C23 N22 C21 C30A 2.0(7) . . . . ?
C21 N22 C23 C23A -26.7(7) . . . . ?
C33 N22 C23 C23A 163.0(6) . . . . ?
N22 C23 C23A C24 158.5(6) . . . . ?
N22 C23 C23A C30A 38.7(6) . . . . ?
C23 C23A C24 C24A -163.8(6) . . . . ?
C30A C23A C24 C24A -48.6(7) . . . . ?
C23A C24 C24A O25 179.0(6) . . . . ?
C23A C24 C24A C29B -2.1(9) . . . . ?
C25A O25 C24A C24 -178.2(6) . . . . ?
C25A O25 C24A C29B 2.8(7) . . . . ?
C24A O25 C25A C29A -0.9(8) . . . . ?
C24A O25 C25A C26 -179.7(6) . . . . ?
C29A C25A C26 C27 -1.2(11) . . . . ?
O25 C25A C26 C27 177.5(6) . . . . ?
C25A C26 C27 C28 2.0(11) . . . . ?
C26 C27 C28 C29 -1.8(12) . . . . ?
C27 C28 C29 C29A 0.8(11) . . . . ?
C26 C25A C29A C29 0.2(11) . . . . ?
O25 C25A C29A C29 -178.6(6) . . . . ?
C26 C25A C29A C29B 177.5(6) . . . . ?
O25 C25A C29A C29B -1.3(8) . . . . ?
C28 C29 C29A C25A 0.0(10) . . . . ?
C28 C29 C29A C29B -176.5(7) . . . . ?
C24 C24A C29B C29A 177.6(6) . . . . ?
O25 C24A C29B C29A -3.4(7) . . . . ?
C24 C24A C29B C30 43.0(9) . . . . ?
O25 C24A C29B C30 -138.0(6) . . . . ?
C25A C29A C29B C24A 2.7(7) . . . . ?
C29 C29A C29B C24A 179.5(7) . . . . ?
C25A C29A C29B C30 131.5(6) . . . . ?
C29 C29A C29B C30 -51.6(11) . . . . ?
C24A C29B C30 C32 94.0(6) . . . . ?
C29A C29B C30 C32 -29.6(8) . . . . ?
C24A C29B C30 C31 -144.7(5) . . . . ?
C29A C29B C30 C31 91.8(7) . . . . ?
C24A C29B C30 C30A -26.0(7) . . . . ?
C29A C29B C30 C30A -149.6(6) . . . . ?
O21 C21 C30A C23A -160.1(7) . . . . ?
N22 C21 C30A C23A 23.4(6) . . . . ?
O21 C21 C30A C30 -31.0(10) . . . . ?
N22 C21 C30A C30 152.5(5) . . . . ?
C24 C23A C30A C21 -166.3(5) . . . . ?
C23 C23A C30A C21 -38.4(6) . . . . ?
C24 C23A C30A C30 62.0(7) . . . . ?
C23 C23A C30A C30 -170.1(5) . . . . ?
C32 C30 C30A C21 93.1(7) . . . . ?
C31 C30 C30A C21 -26.6(8) . . . . ?
C29B C30 C30A C21 -145.1(6) . . . . ?
C32 C30 C30A C23A -143.2(6) . . . . ?
C31 C30 C30A C23A 97.0(6) . . . . ?
C29B C30 C30A C23A -21.5(7) . . . . ?
C32 C30 C31 O22 7.2(9) . . . . ?
C30A C30 C31 O22 126.8(6) . . . . ?
C29B C30 C31 O22 -115.6(7) . . . . ?
C32 C30 C31 O23 -175.0(5) . . . . ?
C30A C30 C31 O23 -55.4(6) . . . . ?
C29B C30 C31 O23 62.2(6) . . . . ?
C31 C30 C32 F22 68.8(7) . . . . ?
C30A C30 C32 F22 -50.8(7) . . . . ?
C29B C30 C32 F22 -170.0(5) . . . . ?
C31 C30 C32 F23 -54.7(8) . . . . ?
C30A C30 C32 F23 -174.3(5) . . . . ?
C29B C30 C32 F23 66.5(8) . . . . ?
C31 C30 C32 F21 -173.0(5) . . . . ?
C30A C30 C32 F21 67.4(7) . . . . ?
C29B C30 C32 F21 -51.8(7) . . . . ?
C21 N22 C33 C34 41.0(9) . . . . ?
C23 N22 C33 C34 -149.8(6) . . . . ?
C21 N22 C33 C38 -139.9(6) . . . . ?
C23 N22 C33 C38 29.3(9) . . . . ?
C38 C33 C34 C35 1.6(10) . . . . ?
N22 C33 C34 C35 -179.3(6) . . . . ?
C33 C34 C35 C36 -0.7(10) . . . . ?
C34 C35 C36 C37 -0.1(10) . . . . ?
C35 C36 C37 C38 -0.1(10) . . . . ?
C36 C37 C38 C33 1.1(10) . . . . ?
C34 C33 C38 C37 -1.9(10) . . . . ?
N22 C33 C38 C37 179.0(6) . . . . ?
