#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:55:05 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178411 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/32/4023207.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_4023207
loop_
_publ_author_name
'Lodovico Lunazzi'
'Andrea Mazzanti'
'Shaik Rafi'
'H. Surya Prakash Rao'
_publ_contact_author
;
Dr. Andrea Mazzanti
University of Bologna
Department of Organic Chemistry A.Mangini
Viale Risorgimento 4
40136 Bologna
Italy
;
_publ_contact_author_email       mazzand@ms.fci.unibo.it
_publ_contact_author_fax         '[039]051 209 3654'
_publ_contact_author_phone       '[039]051 209 3633'
_publ_section_title
;
 Chair to Boat Interconversion and Face to Face Interactions
 in Isomeric Aryl-Substituted Perhydrocyclopentaquinolizines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              678
_journal_page_last               688
_journal_paper_doi               10.1021/jo702172u
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C56 H65 F9 N2 O10'
_chemical_formula_weight         1097.10
_chemical_name_common            'compound 2-H+'
_chemical_name_systematic
; 
 (3R*,5S*,7aR*,9aS*)-3,5-di(4-methoxyphenyl)perhydrocyclopenta[ij]
 quinolizine trifluoroacetate 
;
_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_date             10/09/2007
_audit_creation_method           SHELXL-97
_audit_update_record             13/09/2007
_cell_angle_alpha                110.3030(10)
_cell_angle_beta                 98.6520(10)
_cell_angle_gamma                107.6590(10)
_cell_formula_units_Z            2
_cell_length_a                   11.3651(10)
_cell_length_b                   16.3126(14)
_cell_length_c                   17.2329(15)
_cell_measurement_reflns_used    667
_cell_measurement_temperature    273(2)
_cell_volume                     2735.8(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'bruker APEX2'
_diffrn_measurement_method       'phi and 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  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27537
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         1.44
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_correction_T_min  0.9782
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     739
_refine_ls_number_reflns         10142
_refine_ls_number_restraints     55
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.1354
_refine_ls_R_factor_gt           0.0707
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1169P)²+0.5474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2000
_refine_ls_wR_factor_ref         0.2462
_reflns_number_gt                5004
_reflns_number_total             10142
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702172u-File005.cif
_cod_data_source_block           121bnh
_cod_database_code               4023207
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
N1 N 0.3770(3) 0.20247(19) 0.23528(19) 0.0623(7) Uani 1 1 d . A 5
H101 H 0.438(3) 0.261(2) 0.281(2) 0.068(9) Uiso 1 1 d . B 5
O1 O 0.2935(3) 0.5575(2) 0.2028(2) 0.1123(10) Uani 1 1 d . A 5
O2 O 0.2390(4) 0.1795(2) 0.5758(2) 0.1365(13) Uani 1 1 d . A 5
C1 C 0.2005(3) 0.0690(2) 0.0755(3) 0.0798(10) Uani 1 1 d . A 5
H1A H 0.2182 0.0189 0.0865 0.096 Uiso 1 1 calc R A 5
H1B H 0.1357 0.0399 0.0201 0.096 Uiso 1 1 calc R A 5
C2 C 0.1460(3) 0.1180(2) 0.1456(3) 0.0881(12) Uani 1 1 d . A 5
H2A H 0.0789 0.1333 0.1192 0.106 Uiso 1 1 calc R A 5
H2B H 0.1061 0.0737 0.1687 0.106 Uiso 1 1 calc R A 5
C3 C 0.2443(3) 0.2083(2) 0.2204(2) 0.0726(9) Uani 1 1 d . A 5
H3 H 0.2174 0.2110 0.2724 0.087 Uiso 1 1 calc R A 5
C4 C 0.3817(3) 0.1250(2) 0.2646(2) 0.0726(9) Uani 1 1 d . A 5
H4 H 0.3201 0.0641 0.2194 0.087 Uiso 1 1 calc R A 5
C5 C 0.5149(4) 0.1231(3) 0.2730(3) 0.0871(11) Uani 1 1 d . A 5
H5A H 0.5207 0.0758 0.2937 0.105 Uiso 1 1 calc R A 5
H5B H 0.5781 0.1842 0.3149 0.105 Uiso 1 1 calc R A 5
C6 C 0.5448(4) 0.1006(3) 0.1873(3) 0.0881(12) Uani 1 1 d . A 5
H6A H 0.4808 0.0400 0.1451 0.106 Uiso 1 1 calc R A 5
H6B H 0.6284 0.0957 0.1935 0.106 Uiso 1 1 calc R A 5
C7 C 0.5456(3) 0.1765(2) 0.1553(2) 0.0687(9) Uani 1 1 d . A 5
H7 H 0.6235 0.2336 0.1891 0.082 Uiso 1 1 calc R A 5
C8 C 0.3229(3) 0.1351(2) 0.0700(2) 0.0690(9) Uani 1 1 d . A 5
H8 H 0.2993 0.1747 0.0441 0.083 Uiso 1 1 calc R A 5
C9 C 0.4251(3) 0.2011(2) 0.1579(2) 0.0596(8) Uani 1 1 d . A 5
H9 H 0.4496 0.2654 0.1611 0.071 Uiso 1 1 calc R A 5
C10 C 0.5357(4) 0.1442(3) 0.0597(3) 0.0818(11) Uani 1 1 d . A 5
H10A H 0.5629 0.1979 0.0451 0.098 Uiso 1 1 calc R A 5
H10B H 0.5884 0.1076 0.0438 0.098 Uiso 1 1 calc R A 5
C11 C 0.3942(4) 0.0837(3) 0.0149(3) 0.0899(11) Uani 1 1 d . A 5
H11A H 0.3739 0.0205 0.0126 0.108 Uiso 1 1 calc R A 5
H11B H 0.3711 0.0789 -0.0435 0.108 Uiso 1 1 calc R A 5
C12 C 0.2570(3) 0.3012(2) 0.2142(2) 0.0668(9) Uani 1 1 d . A 5
C13 C 0.3148(4) 0.3838(3) 0.2885(3) 0.0813(10) Uani 1 1 d . A 5
H13 H 0.3445 0.3810 0.3404 0.098 Uiso 1 1 calc R A 5
C14 C 0.3297(4) 0.4712(3) 0.2878(3) 0.0875(11) Uani 1 1 d . A 5
H14 H 0.3692 0.5262 0.3386 0.105 Uiso 1 1 calc R A 5
C15 C 0.2851(4) 0.4755(3) 0.2109(3) 0.0796(11) Uani 1 1 d . A 5
C16 C 0.2275(4) 0.3940(3) 0.1364(3) 0.0836(11) Uani 1 1 d . A 5
H16 H 0.1983 0.3969 0.0843 0.100 Uiso 1 1 calc R A 5
C17 C 0.2128(3) 0.3079(3) 0.1384(3) 0.0761(10) Uani 1 1 d . A 5
H17 H 0.1721 0.2531 0.0876 0.091 Uiso 1 1 calc R A 5
C18 C 0.3409(4) 0.1399(3) 0.3470(3) 0.0787(10) Uani 1 1 d . A 5
C19 C 0.2445(4) 0.0672(3) 0.3502(3) 0.0866(11) Uani 1 1 d . A 5
H19 H 0.2030 0.0102 0.3015 0.104 Uiso 1 1 calc R A 5
C20 C 0.2078(4) 0.0782(3) 0.4266(3) 0.0944(12) Uani 1 1 d . A 5
H20 H 0.1428 0.0285 0.4284 0.113 Uiso 1 1 calc R A 5
C21 C 0.2682(5) 0.1621(3) 0.4981(3) 0.1013(13) Uani 1 1 d . A 5
C22 C 0.3626(5) 0.2336(3) 0.4943(3) 0.1210(17) Uani 1 1 d . A 5
H22 H 0.4024 0.2912 0.5426 0.145 Uiso 1 1 calc R A 5
C23 C 0.4007(5) 0.2229(3) 0.4210(3) 0.1104(15) Uani 1 1 d . A 5
H23 H 0.4682 0.2724 0.4211 0.132 Uiso 1 1 calc R A 5
C24 C 0.3416(6) 0.6423(3) 0.2782(4) 0.149(2) Uani 1 1 d . A 5
H24A H 0.3450 0.6941 0.2629 0.223 Uiso 1 1 calc R A 5
H24B H 0.4266 0.6528 0.3085 0.223 Uiso 1 1 calc R A 5
H24C H 0.2859 0.6379 0.3146 0.223 Uiso 1 1 calc R A 5
C25 C 0.1362(6) 0.1095(4) 0.5799(4) 0.162(3) Uani 1 1 d . A 5
H25A H 0.1262 0.1306 0.6369 0.242 Uiso 1 1 calc R A 5
H25B H 0.1531 0.0527 0.5666 0.242 Uiso 1 1 calc R A 5
H25C H 0.0586 0.0969 0.5389 0.242 Uiso 1 1 calc R A 5
N2 N 0.8277(2) 0.50117(17) 0.21136(18) 0.0586(7) Uani 1 1 d . C 5
H102 H 0.814(3) 0.491(2) 0.261(2) 0.068(9) Uiso 1 1 d . D 5
O3 O 1.2811(3) 0.8552(2) 0.52548(19) 0.1410(14) Uani 1 1 d . C 5
O4 O 0.8873(3) 0.1274(2) 0.2138(2) 0.1120(10) Uani 1 1 d . C 5
C101 C 0.8429(4) 0.4680(3) 0.0432(2) 0.0755(10) Uani 1 1 d . C 5
H10C H 0.8370 0.5284 0.0514 0.091 Uiso 1 1 calc R C 5
H10D H 0.8520 0.4403 -0.0142 0.091 Uiso 1 1 calc R C 5
C102 C 0.9633(3) 0.4854(3) 0.1096(2) 0.0776(10) Uani 1 1 d . C 5
H10E H 1.0253 0.5486 0.1254 0.093 Uiso 1 1 calc R C 5
H10F H 1.0012 0.4411 0.0823 0.093 Uiso 1 1 calc R C 5
C103 C 0.9425(3) 0.4758(2) 0.1921(2) 0.0646(8) Uani 1 1 d . C 5
H103 H 1.0189 0.5236 0.2393 0.078 Uiso 1 1 calc R C 5
C104 C 0.8528(3) 0.6049(2) 0.2335(2) 0.0680(9) Uani 1 1 d . C 5
H104 H 0.8701 0.6176 0.1839 0.082 Uiso 1 1 calc R C 5
C105 C 0.7314(4) 0.6216(3) 0.2468(3) 0.0835(11) Uani 1 1 d . C 5
H10G H 0.7107 0.6072 0.2944 0.100 Uiso 1 1 calc R C 5
H10H H 0.7466 0.6877 0.2619 0.100 Uiso 1 1 calc R C 5
C106 C 0.6183(4) 0.5607(2) 0.1662(3) 0.0829(11) Uani 1 1 d . C 5
H10I H 0.6387 0.5752 0.1186 0.099 Uiso 1 1 calc R C 5
H10J H 0.5435 0.5750 0.1758 0.099 Uiso 1 1 calc R C 5
C107 C 0.5868(3) 0.4558(2) 0.1425(2) 0.0692(9) Uani 1 1 d . C 5
H107 H 0.5445 0.4369 0.1825 0.083 Uiso 1 1 calc R C 5
C108 C 0.7188(3) 0.4036(2) 0.0482(2) 0.0658(9) Uani 1 1 d . C 5
H108 H 0.7168 0.3390 0.0258 0.079 Uiso 1 1 calc R C 5
C109 C 0.7053(3) 0.4296(2) 0.14107(19) 0.0573(8) Uani 1 1 d . C 5
H109 H 0.6845 0.3713 0.1500 0.069 Uiso 1 1 calc R C 5
C110 C 0.5959(4) 0.4023(3) -0.0035(2) 0.0849(11) Uani 1 1 d . C 5
H11C H 0.6132 0.4600 -0.0121 0.102 Uiso 1 1 calc R C 5
H11D H 0.5612 0.3487 -0.0594 0.102 Uiso 1 1 calc R C 5
C111 C 0.5024(3) 0.3943(3) 0.0503(2) 0.0792(10) Uani 1 1 d . C 5
H11E H 0.4606 0.3292 0.0419 0.095 Uiso 1 1 calc R C 5
H11F H 0.4371 0.4176 0.0355 0.095 Uiso 1 1 calc R C 5
C112 C 0.9690(3) 0.6688(2) 0.3103(2) 0.0722(9) Uani 1 1 d . C 5
C113 C 0.9759(5) 0.6691(3) 0.3914(3) 0.1153(17) Uani 1 1 d . C 5
H113 H 0.9079 0.6266 0.3991 0.138 Uiso 1 1 calc R C 5
C114 C 1.0806(5) 0.7306(4) 0.4598(3) 0.135(2) Uani 1 1 d . C 5
H114 H 1.0833 0.7287 0.5134 0.161 Uiso 1 1 calc R C 5
C115 C 1.1826(4) 0.7956(3) 0.4520(3) 0.0973(13) Uani 1 1 d . C 5
C116 C 1.1779(4) 0.7973(2) 0.3730(2) 0.0782(10) Uani 1 1 d . C 5
H116 H 1.2452 0.8413 0.3662 0.094 Uiso 1 1 calc R C 5
C117 C 1.0726(3) 0.7332(2) 0.3031(2) 0.0720(9) Uani 1 1 d . C 5
H117 H 1.0717 0.7337 0.2492 0.086 Uiso 1 1 calc R C 5
C118 C 0.9263(3) 0.3812(3) 0.1960(2) 0.0651(9) Uani 1 1 d . C 5
C119 C 0.8917(3) 0.2979(3) 0.1248(3) 0.0726(9) Uani 1 1 d . C 5
H119 H 0.8768 0.2975 0.0701 0.087 Uiso 1 1 calc R C 5
C120 C 0.8787(3) 0.2146(3) 0.1328(3) 0.0780(10) Uani 1 1 d . C 5
H120 H 0.8536 0.1586 0.0837 0.094 Uiso 1 1 calc R C 5
C121 C 0.9027(4) 0.2140(3) 0.2134(3) 0.0859(12) Uani 1 1 d . C 5
C122 C 0.9399(4) 0.2970(3) 0.2855(3) 0.0891(11) Uani 1 1 d . C 5
H122 H 0.9572 0.2974 0.3402 0.107 Uiso 1 1 calc R C 5
C123 C 0.9517(3) 0.3797(3) 0.2766(3) 0.0826(10) Uani 1 1 d . C 5
H123 H 0.9772 0.4357 0.3258 0.099 Uiso 1 1 calc R C 5
C124 C 1.3899(5) 0.9199(4) 0.5178(3) 0.134(2) Uani 1 1 d . C 5
H12A H 1.4516 0.9584 0.5736 0.201 Uiso 1 1 calc R C 5
H12B H 1.3633 0.9596 0.4951 0.201 Uiso 1 1 calc R C 5
H12C H 1.4284 0.8855 0.4794 0.201 Uiso 1 1 calc R C 5
C125 C 0.9128(5) 0.1230(4) 0.2956(4) 0.137(2) Uani 1 1 d . C 5
H12D H 0.8987 0.0590 0.2871 0.205 Uiso 1 1 calc R C 5
H12E H 0.8563 0.1438 0.3265 0.205 Uiso 1 1 calc R C 5
H12F H 1.0007 0.1633 0.3283 0.205 Uiso 1 1 calc R C 5
C51 C 1.0495(6) 0.7949(4) 0.1097(3) 0.1065(15) Uani 1 1 d . E 5
C52 C 0.9380(6) 0.8214(4) 0.1249(3) 0.1131(16) Uani 1 1 d . E 5
F1 F 0.9501(4) 0.8641(3) 0.2062(3) 0.1897(16) Uani 1 1 d . E 5
F2 F 0.9210(4) 0.8775(3) 0.0902(3) 0.1982(18) Uani 1 1 d . E 5
F3 F 0.8287(4) 0.7497(3) 0.0938(3) 0.1986(17) Uani 1 1 d . E 5
O5 O 1.0343(4) 0.7127(3) 0.0840(2) 0.1478(15) Uani 1 1 d . E 5
O6 O 1.1489(4) 0.8636(3) 0.1279(3) 0.1682(16) Uani 1 1 d . E 5
H6 H 1.2074 0.8456 0.1184 0.252 Uiso 1 1 calc R E 5
C53 C 0.4180(7) 0.8599(4) 0.2081(5) 0.1148(16) Uani 1 1 d . F 5
C54 C 0.5500(7) 0.8610(5) 0.2195(5) 0.138(2) Uani 1 1 d . F 5
F4 F 0.5847(6) 0.8456(6) 0.1463(5) 0.280(3) Uani 1 1 d . F 5
F5 F 0.5665(4) 0.7933(4) 0.2298(4) 0.214(2) Uani 1 1 d . F 5
F6 F 0.6352(5) 0.9376(3) 0.2650(5) 0.276(4) Uani 1 1 d . F 5
O7 O 0.3580(5) 0.8381(3) 0.1330(3) 0.1724(17) Uani 1 1 d . F 5
O8 O 0.3851(5) 0.8835(3) 0.2716(3) 0.1746(18) Uani 1 1 d . F 5
O9 O 0.7391(3) 0.4676(2) 0.3399(2) 0.1259(12) Uani 1 1 d . G 5
O10 O 0.5850(3) 0.3594(2) 0.3499(2) 0.1276(12) Uani 1 1 d . G 5
C98 C 0.6794(4) 0.4285(3) 0.3762(2) 0.0720(9) Uani 1 1 d D G 5
F7 F 0.6065(13) 0.4726(11) 0.4975(7) 0.242(6) Uani 0.488(10) 1 d PDU H 1
F8 F 0.7989(15) 0.5601(13) 0.5133(10) 0.212(7) Uani 0.488(10) 1 d PDU H 1
F9 F 0.7665(19) 0.4334(16) 0.5082(11) 0.249(7) Uani 0.488(10) 1 d PDU H 1
C99 C 0.7088(12) 0.4781(9) 0.4761(8) 0.119(5) Uani 0.488(10) 1 d PDU H 1
F7A F 0.7026(17) 0.4274(15) 0.5146(9) 0.214(7) Uani 0.512(10) 1 d PU H 2
F8A F 0.8788(10) 0.4958(12) 0.4842(7) 0.242(6) Uani 0.512(10) 1 d PU H 2
F9A F 0.7263(18) 0.5578(14) 0.5026(11) 0.237(7) Uani 0.512(10) 1 d PU H 2
C99A C 0.7654(19) 0.4770(14) 0.4728(8) 0.137(6) Uani 0.512(10) 1 d PDU H 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'
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
C9 N1 C4 116.2(2) . . ?
C9 N1 C3 109.0(2) . . ?
C4 N1 C3 113.2(2) . . ?
C9 N1 H101 103.1(18) . . ?
C4 N1 H101 105.2(18) . . ?
C3 N1 H101 109.4(18) . . ?
C15 O1 C24 118.4(4) . . ?
C21 O2 C25 118.0(4) . . ?
C8 C1 C2 113.7(3) . . ?
C8 C1 H1A 108.8 . . ?
C2 C1 H1A 108.8 . . ?
C8 C1 H1B 108.8 . . ?
C2 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
C3 C2 C1 115.1(3) . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2B 108.5 . . ?
C1 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C12 C3 C2 116.7(3) . . ?
C12 C3 N1 109.1(2) . . ?
C2 C3 N1 110.3(3) . . ?
C12 C3 H3 106.7 . . ?
C2 C3 H3 106.7 . . ?
N1 C3 H3 106.7 . . ?
C5 C4 C18 113.9(3) . . ?
C5 C4 N1 108.3(3) . . ?
C18 C4 N1 110.3(3) . . ?
C5 C4 H4 108.1 . . ?
C18 C4 H4 108.1 . . ?
N1 C4 H4 108.1 . . ?
C4 C5 C6 111.0(3) . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C5 C6 C7 111.2(3) . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 C10 112.9(3) . . ?
C6 C7 C9 113.1(3) . . ?
C10 C7 C9 100.8(3) . . ?
C6 C7 H7 109.9 . . ?
C10 C7 H7 109.9 . . ?
C9 C7 H7 109.9 . . ?
C1 C8 C11 113.8(3) . . ?
C1 C8 C9 114.4(3) . . ?
C11 C8 C9 104.5(3) . . ?
C1 C8 H8 107.9 . . ?
C11 C8 H8 107.9 . . ?
C9 C8 H8 107.9 . . ?
N1 C9 C7 115.0(3) . . ?
N1 C9 C8 114.3(3) . . ?
C7 C9 C8 107.3(3) . . ?
N1 C9 H9 106.5 . . ?
C7 C9 H9 106.5 . . ?
C8 C9 H9 106.5 . . ?
C11 C10 C7 104.2(3) . . ?
C11 C10 H10A 110.9 . . ?
C7 C10 H10A 110.9 . . ?
C11 C10 H10B 110.9 . . ?
C7 C10 H10B 110.9 . . ?
H10A C10 H10B 108.9 . . ?
C10 C11 C8 104.8(3) . . ?
C10 C11 H11A 110.8 . . ?
C8 C11 H11A 110.8 . . ?
C10 C11 H11B 110.8 . . ?
C8 C11 H11B 110.8 . . ?
H11A C11 H11B 108.9 . . ?
C13 C12 C17 117.6(3) . . ?
C13 C12 C3 118.5(3) . . ?
C17 C12 C3 123.9(3) . . ?
C12 C13 C14 121.8(4) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C15 C14 C13 119.2(4) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
O1 C15 C16 115.9(4) . . ?
O1 C15 C14 124.2(4) . . ?
C16 C15 C14 119.8(4) . . ?
C15 C16 C17 120.1(4) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 121.5(4) . . ?
C16 C17 H17 119.2 . . ?
C12 C17 H17 119.2 . . ?
C19 C18 C23 117.7(4) . . ?
C19 C18 C4 119.5(3) . . ?
C23 C18 C4 122.8(3) . . ?
C18 C19 C20 120.6(4) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C21 C20 C19 119.7(4) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C22 C21 C20 119.3(4) . . ?
C22 C21 O2 116.7(4) . . ?
C20 C21 O2 124.0(4) . . ?
C21 C22 C23 121.3(4) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C22 C23 C18 121.3(4) . . ?
C22 C23 H23 119.4 . . ?
C18 C23 H23 119.4 . . ?
O1 C24 H24A 109.5 . . ?
O1 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O1 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O2 C25 H25A 109.5 . . ?
O2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C109 N2 C104 116.3(2) . . ?
C109 N2 C103 109.7(2) . . ?
C104 N2 C103 112.7(2) . . ?
C109 N2 H102 103.2(19) . . ?
C104 N2 H102 106.4(19) . . ?
C103 N2 H102 107.7(19) . . ?
C115 O3 C124 117.2(3) . . ?
C121 O4 C125 117.6(4) . . ?
C108 C101 C102 113.9(3) . . ?
C108 C101 H10C 108.8 . . ?
C102 C101 H10C 108.8 . . ?
C108 C101 H10D 108.8 . . ?
C102 C101 H10D 108.8 . . ?
H10C C101 H10D 107.7 . . ?
C101 C102 C103 115.8(3) . . ?
C101 C102 H10E 108.3 . . ?
C103 C102 H10E 108.3 . . ?
C101 C102 H10F 108.3 . . ?
C103 C102 H10F 108.3 . . ?
H10E C102 H10F 107.4 . . ?
C118 C103 C102 117.3(3) . . ?
C118 C103 N2 109.3(2) . . ?
C102 C103 N2 109.7(3) . . ?
C118 C103 H103 106.7 . . ?
C102 C103 H103 106.7 . . ?
N2 C103 H103 106.7 . . ?
C112 C104 C105 112.8(3) . . ?
C112 C104 N2 111.2(3) . . ?
C105 C104 N2 108.6(3) . . ?
C112 C104 H104 108.0 . . ?
C105 C104 H104 108.0 . . ?
N2 C104 H104 108.0 . . ?
C106 C105 C104 111.4(3) . . ?
C106 C105 H10G 109.3 . . ?
C104 C105 H10G 109.3 . . ?
C106 C105 H10H 109.3 . . ?
C104 C105 H10H 109.3 . . ?
H10G C105 H10H 108.0 . . ?
C105 C106 C107 111.1(3) . . ?
C105 C106 H10I 109.4 . . ?
C107 C106 H10I 109.4 . . ?
C105 C106 H10J 109.4 . . ?
C107 C106 H10J 109.4 . . ?
H10I C106 H10J 108.0 . . ?
C111 C107 C106 112.1(3) . . ?
C111 C107 C109 101.5(3) . . ?
C106 C107 C109 113.2(3) . . ?
C111 C107 H107 109.9 . . ?
C106 C107 H107 109.9 . . ?
C109 C107 H107 109.9 . . ?
C101 C108 C110 114.6(3) . . ?
C101 C108 C109 113.9(3) . . ?
C110 C108 C109 104.2(3) . . ?
C101 C108 H108 107.9 . . ?
C110 C108 H108 107.9 . . ?
C109 C108 H108 107.9 . . ?
N2 C109 C107 115.5(2) . . ?
N2 C109 C108 114.2(2) . . ?
C107 C109 C108 107.2(3) . . ?
N2 C109 H109 106.4 . . ?
C107 C109 H109 106.4 . . ?
C108 C109 H109 106.4 . . ?
C111 C110 C108 105.5(3) . . ?
C111 C110 H11C 110.7 . . ?
C108 C110 H11C 110.7 . . ?
C111 C110 H11D 110.7 . . ?
C108 C110 H11D 110.7 . . ?
H11C C110 H11D 108.8 . . ?
C110 C111 C107 103.9(3) . . ?
C110 C111 H11E 111.0 . . ?
C107 C111 H11E 111.0 . . ?
C110 C111 H11F 111.0 . . ?
C107 C111 H11F 111.0 . . ?
H11E C111 H11F 109.0 . . ?
C117 C112 C113 116.8(3) . . ?
C117 C112 C104 120.4(3) . . ?
C113 C112 C104 122.8(3) . . ?
C114 C113 C112 120.9(4) . . ?
C114 C113 H113 119.5 . . ?
C112 C113 H113 119.5 . . ?
C113 C114 C115 121.6(4) . . ?
C113 C114 H114 119.2 . . ?
C115 C114 H114 119.2 . . ?
C116 C115 O3 124.9(3) . . ?
C116 C115 C114 118.6(4) . . ?
O3 C115 C114 116.5(4) . . ?
C115 C116 C117 119.6(3) . . ?
C115 C116 H116 120.2 . . ?
C117 C116 H116 120.2 . . ?
C112 C117 C116 122.4(3) . . ?
C112 C117 H117 118.8 . . ?
C116 C117 H117 118.8 . . ?
C119 C118 C123 117.8(3) . . ?
C119 C118 C103 124.1(3) . . ?
C123 C118 C103 118.1(3) . . ?
C118 C119 C120 121.2(4) . . ?
C118 C119 H119 119.4 . . ?
C120 C119 H119 119.4 . . ?
C119 C120 C121 120.3(4) . . ?
C119 C120 H120 119.9 . . ?
C121 C120 H120 119.9 . . ?
C122 C121 O4 125.3(4) . . ?
C122 C121 C120 119.4(4) . . ?
O4 C121 C120 115.3(4) . . ?
C121 C122 C123 119.8(4) . . ?
C121 C122 H122 120.1 . . ?
C123 C122 H122 120.1 . . ?
C122 C123 C118 121.5(4) . . ?
C122 C123 H123 119.3 . . ?
C118 C123 H123 119.3 . . ?
O3 C124 H12A 109.5 . . ?
O3 C124 H12B 109.5 . . ?
H12A C124 H12B 109.5 . . ?
O3 C124 H12C 109.5 . . ?
H12A C124 H12C 109.5 . . ?
H12B C124 H12C 109.5 . . ?
O4 C125 H12D 109.5 . . ?
O4 C125 H12E 109.5 . . ?
H12D C125 H12E 109.5 . . ?
O4 C125 H12F 109.5 . . ?
H12D C125 H12F 109.5 . . ?
H12E C125 H12F 109.5 . . ?
O5 C51 O6 128.3(7) . . ?
O5 C51 C52 118.6(5) . . ?
O6 C51 C52 113.1(5) . . ?
F1 C52 F3 105.7(6) . . ?
F1 C52 F2 106.3(5) . . ?
F3 C52 F2 104.9(5) . . ?
F1 C52 C51 112.3(5) . . ?
F3 C52 C51 113.7(5) . . ?
F2 C52 C51 113.1(5) . . ?
C51 O6 H6 109.5 . . ?
O8 C53 O7 128.4(7) . . ?
O8 C53 C54 116.5(7) . . ?
O7 C53 C54 114.9(6) . . ?
F6 C54 F5 114.8(8) . . ?
F6 C54 F4 98.7(7) . . ?
F5 C54 F4 95.9(7) . . ?
F6 C54 C53 115.1(7) . . ?
F5 C54 C53 116.7(6) . . ?
F4 C54 C53 112.3(7) . . ?
O10 C98 O9 131.3(4) . . ?
F7 C99 F8 114.7(15) . . ?
F7 C99 F9 109.8(15) . . ?
F8 C99 F9 98.0(15) . . ?
F8A C99A F7A 118.5(18) . . ?
F8A C99A F9A 116.0(18) . . ?
F7A C99A F9A 98.1(18) . . ?
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
N1 C9 1.511(4) . ?
N1 C4 1.528(4) . ?
N1 C3 1.529(4) . ?
N1 H101 0.96(3) . ?
O1 C15 1.369(4) . ?
O1 C24 1.407(6) . ?
O2 C21 1.383(5) . ?
O2 C25 1.394(5) . ?
C1 C8 1.518(5) . ?
C1 C2 1.530(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.526(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C12 1.521(5) . ?
C3 H3 0.9800 . ?
C4 C5 1.510(5) . ?
C4 C18 1.521(5) . ?
C4 H4 0.9800 . ?
C5 C6 1.511(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.517(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C10 1.520(5) . ?
C7 C9 1.542(4) . ?
C7 H7 0.9800 . ?
C8 C11 1.534(5) . ?
C8 C9 1.544(5) . ?
C8 H8 0.9800 . ?
C9 H9 0.9800 . ?
C10 C11 1.514(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.378(5) . ?
C12 C17 1.381(5) . ?
C13 C14 1.387(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(5) . ?
C16 C17 1.376(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.374(5) . ?
C18 C23 1.379(5) . ?
C19 C20 1.410(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.366(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.352(6) . ?
C22 C23 1.368(6) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
N2 C109 1.514(4) . ?
N2 C104 1.523(4) . ?
N2 C103 1.532(4) . ?
N2 H102 0.94(3) . ?
O3 C115 1.365(5) . ?
O3 C124 1.419(5) . ?
O4 C121 1.373(5) . ?
O4 C125 1.427(6) . ?
C101 C108 1.517(4) . ?
C101 C102 1.527(5) . ?
C101 H10C 0.9700 . ?
C101 H10D 0.9700 . ?
C102 C103 1.528(4) . ?
C102 H10E 0.9700 . ?
C102 H10F 0.9700 . ?
C103 C118 1.524(4) . ?
C103 H103 0.9800 . ?
C104 C112 1.505(5) . ?
C104 C105 1.520(5) . ?
C104 H104 0.9800 . ?
C105 C106 1.516(5) . ?
C105 H10G 0.9700 . ?
C105 H10H 0.9700 . ?
C106 C107 1.524(5) . ?
C106 H10I 0.9700 . ?
C106 H10J 0.9700 . ?
C107 C111 1.517(5) . ?
C107 C109 1.532(4) . ?
C107 H107 0.9800 . ?
C108 C110 1.529(5) . ?
C108 C109 1.552(4) . ?
C108 H108 0.9800 . ?
C109 H109 0.9800 . ?
C110 C111 1.517(5) . ?
C110 H11C 0.9700 . ?
C110 H11D 0.9700 . ?
C111 H11E 0.9700 . ?
C111 H11F 0.9700 . ?
C112 C117 1.374(4) . ?
C112 C113 1.387(5) . ?
C113 C114 1.358(6) . ?
C113 H113 0.9300 . ?
C114 C115 1.374(5) . ?
C114 H114 0.9300 . ?
C115 C116 1.364(5) . ?
C116 C117 1.382(5) . ?
C116 H116 0.9300 . ?
C117 H117 0.9300 . ?
C118 C119 1.373(5) . ?
C118 C123 1.386(5) . ?
C119 C120 1.378(5) . ?
C119 H119 0.9300 . ?
C120 C121 1.379(5) . ?
C120 H120 0.9300 . ?
C121 C122 1.371(6) . ?
C122 C123 1.379(5) . ?
C122 H122 0.9300 . ?
C123 H123 0.9300 . ?
C124 H12A 0.9600 . ?
C124 H12B 0.9600 . ?
C124 H12C 0.9600 . ?
C125 H12D 0.9600 . ?
C125 H12E 0.9600 . ?
C125 H12F 0.9600 . ?
C51 O5 1.203(5) . ?
C51 O6 1.230(5) . ?
C51 C52 1.488(8) . ?
C52 F1 1.294(6) . ?
C52 F3 1.296(6) . ?
C52 F2 1.297(5) . ?
O6 H6 0.8200 . ?
C53 O8 1.184(6) . ?
C53 O7 1.240(6) . ?
C53 C54 1.478(9) . ?
C54 F6 1.213(7) . ?
C54 F5 1.240(7) . ?
C54 F4 1.340(8) . ?
O9 C98 1.184(4) . ?
O10 C98 1.180(4) . ?
F7 C99 1.259(14) . ?
F8 C99 1.275(15) . ?
F9 C99 1.315(17) . ?
F7A C99A 1.37(2) . ?
F8A C99A 1.20(2) . ?
F9A C99A 1.47(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 H101 O10 0.96(3) 1.80(3) 2.731(4) 163(3) .
N2 H102 O9 0.94(3) 1.81(3) 2.720(4) 162(3) .
O6 H6 O7 0.82 1.74 2.528(7) 160.5 1_655
