#------------------------------------------------------------------------------
#$Date: 2025-08-22 14:50:14 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301863 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/36/7203677.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_7203677
loop_
_publ_author_name
'Oyston, Stephen'
'Wang, Changsheng'
'Hughes, Gregory'
'Batsanov, Andrei S.'
'Perepichka, Igor F.'
'Bryce, Martin R.'
'Ahn, Jin H.'
'Pearson, Christopher'
'Petty, Michael C.'
_publ_section_title
;
 New 2,5-diaryl-1,3,4-oxadiazole?fluorene hybrids as electron
 transporting materials for blended-layer organic light emitting diodes
;
_journal_issue                   1
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              194
_journal_paper_doi               10.1039/b413066a
_journal_volume                  15
_journal_year                    2005
_chemical_formula_moiety         'C77 H98 N4 O4'
_chemical_formula_sum            'C77 H98 N4 O4'
_chemical_formula_weight         1143.59
_chemical_melting_point          434.9(3)
_chemical_name_systematic
; 2,7-Bis{4-[2-(4-dodecyloxyphenyl)-1,3,4-oxadiazol-5-yl]phenyl}-
9,9-dihexylfluorene
;
_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                90.56(1)
_cell_angle_beta                 95.93(1)
_cell_angle_gamma                107.64(1)
_cell_formula_units_Z            2
_cell_length_a                   12.7434(9)
_cell_length_b                   15.6535(11)
_cell_length_c                   17.7496(13)
_cell_measurement_reflns_used    908
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      19.73
_cell_measurement_theta_min      10.19
_cell_volume                     3353.0(5)
_computing_cell_refinement       'SMART version 5.060 (Bruker, 1999)'
_computing_data_collection       'SMART version 5.049 (Bruker, 1998)'
_computing_data_reduction        'SAINT version 6.02A (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL version 6.12 (Bruker, 2001)'
_computing_publication_material  'SHELXTL version 6.12 (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'SMART 1K CCD area detector'
_diffrn_measurement_method       'ω 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  0.0582
_diffrn_reflns_av_sigmaI/netI    0.0787
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            34169
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       plate
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     775
_refine_ls_number_reflns         15321
_refine_ls_number_restraints     52
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0573
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0512P)²+1.0065P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1402
_reflns_number_gt                9543
_reflns_number_total             15321
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b413066a.txt
_cod_data_source_block           (11)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/adriana/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '434.7--435.2' was changed to
'434.9(3)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_cell_volume        3353.0(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7203677
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
O1 O 0.98487(10) 0.22846(8) 0.44239(7) 0.0196(3) Uani 1 1 d . . .
O2 O 1.63018(10) 0.08855(8) -0.48499(7) 0.0198(3) Uani 1 1 d . . .
O3 O 0.58055(11) 0.34835(9) 0.54150(8) 0.0256(3) Uani 1 1 d . . .
O4 O 1.89984(11) -0.00416(9) -0.74301(7) 0.0261(3) Uani 1 1 d . . .
N1 N 1.08325(14) 0.17382(12) 0.52754(10) 0.0283(4) Uani 1 1 d . . .
N2 N 1.00537(14) 0.20235(12) 0.56398(10) 0.0294(4) Uani 1 1 d . . .
N3 N 1.48287(13) 0.13168(10) -0.51935(9) 0.0216(4) Uani 1 1 d . . .
N4 N 1.53055(13) 0.11835(10) -0.58499(9) 0.0213(4) Uani 1 1 d . . .
C1 C 1.24188(15) 0.12840(12) 0.13062(11) 0.0206(4) Uani 1 1 d . . .
H1 H 1.1662 0.1257 0.1224 0.025 Uiso 1 1 d R . .
C2 C 1.29475(15) 0.13673(12) 0.20487(11) 0.0192(4) Uani 1 1 d . . .
C3 C 1.40650(15) 0.13853(13) 0.21550(11) 0.0225(4) Uani 1 1 d . . .
H3 H 1.4431 0.1437 0.2654 0.027 Uiso 1 1 d R . .
C4 C 1.46383(16) 0.13322(13) 0.15421(11) 0.0238(4) Uani 1 1 d . . .
H4 H 1.5385 0.1331 0.1623 0.029 Uiso 1 1 d R . .
C5 C 1.55400(16) 0.12646(13) -0.01320(11) 0.0233(4) Uani 1 1 d . . .
H5 H 1.6128 0.1282 0.0247 0.028 Uiso 1 1 d R . .
C6 C 1.56951(16) 0.12490(13) -0.08903(11) 0.0245(4) Uani 1 1 d . . .
H6 H 1.6398 0.1259 -0.1027 0.029 Uiso 1 1 d R . .
C7 C 1.48414(15) 0.12216(12) -0.14648(11) 0.0211(4) Uani 1 1 d . . .
C8 C 1.37959(15) 0.11968(13) -0.12557(11) 0.0213(4) Uani 1 1 d . . .
H8 H 1.3200 0.1163 -0.1633 0.026 Uiso 1 1 d R . .
C9 C 1.25914(15) 0.12099(13) -0.01482(11) 0.0208(4) Uani 1 1 d . . .
C10 C 1.29917(15) 0.12444(13) 0.06935(11) 0.0207(4) Uani 1 1 d . . .
C11 C 1.41098(15) 0.12763(12) 0.08075(11) 0.0206(4) Uani 1 1 d . . .
C12 C 1.45074(15) 0.12546(12) 0.00641(11) 0.0209(4) Uani 1 1 d . . .
C13 C 1.36416(15) 0.12220(12) -0.04960(11) 0.0202(4) Uani 1 1 d . . .
C14 C 1.16304(15) 0.03500(13) -0.04042(11) 0.0224(4) Uani 1 1 d . . .
H141 H 1.0993 0.0346 -0.0130 0.029 Uiso 1 1 d R . .
H142 H 1.1402 0.0383 -0.0949 0.029 Uiso 1 1 d R . .
C15 C 1.18674(18) -0.05275(14) -0.02864(14) 0.0371(6) Uani 1 1 d . A .
H151 H 1.1970 -0.0618 0.0263 0.048 Uiso 1 1 d R . .
H152 H 1.2566 -0.0500 -0.0494 0.048 Uiso 1 1 d R . .
C16 C 1.09527(17) -0.13255(14) -0.06606(13) 0.0334(5) Uani 1 1 d D . .
H161 H 1.0233 -0.1407 -0.0516 0.043 Uiso 1 1 d R A .
H162 H 1.0714 -0.1137 -0.1225 0.043 Uiso 1 1 d R . .
C17A C 1.1277(4) -0.2171(3) -0.0801(3) 0.0324(10) Uiso 0.50 1 d PD A 1
H171 H 1.1700 -0.2287 -0.0335 0.042 Uiso 0.50 1 d PR A 1
H172 H 1.1769 -0.2067 -0.1208 0.042 Uiso 0.50 1 d PR A 1
C18A C 1.0334(5) -0.2954(4) -0.1177(4) 0.0450(15) Uiso 0.50 1 d PD A 1
H181 H 1.0105 -0.2793 -0.1691 0.059 Uiso 0.50 1 d PR A 1
H182 H 0.9693 -0.3062 -0.0882 0.059 Uiso 0.50 1 d PR A 1
C19A C 1.0647(5) -0.3818(3) -0.1231(3) 0.0576(15) Uani 0.50 1 d PD A 1
H191 H 0.9978 -0.4324 -0.1375 0.086 Uiso 0.50 1 d PR A 1
H192 H 1.1002 -0.3920 -0.0738 0.086 Uiso 0.50 1 d PR A 1
H193 H 1.1162 -0.3764 -0.1614 0.086 Uiso 0.50 1 d PR A 1
C17B C 1.1084(4) -0.2234(3) -0.0417(3) 0.0431(12) Uiso 0.50 1 d PD A 2
H173 H 1.0865 -0.2358 0.0098 0.056 Uiso 0.50 1 d PR A 2
H174 H 1.1863 -0.2225 -0.0415 0.056 Uiso 0.50 1 d PR A 2
C18B C 1.0288(5) -0.3035(4) -0.0886(3) 0.0446(16) Uiso 0.50 1 d PD A 2
H183 H 1.0283 -0.3591 -0.0627 0.058 Uiso 0.50 1 d PR A 2
H184 H 0.9531 -0.2984 -0.0919 0.058 Uiso 0.50 1 d PR A 2
C19B C 1.0606(5) -0.3097(4) -0.1676(3) 0.0648(17) Uani 0.50 1 d PD A 2
H194 H 1.0031 -0.3578 -0.1974 0.097 Uiso 0.50 1 d PR A 2
H195 H 1.1313 -0.3230 -0.1647 0.097 Uiso 0.50 1 d PR A 2
H196 H 1.0682 -0.2526 -0.1920 0.097 Uiso 0.50 1 d PR A 2
C20 C 1.22015(15) 0.20260(13) -0.03610(11) 0.0227(4) Uani 1 1 d . . .
H201 H 1.1916 0.1951 -0.0904 0.030 Uiso 1 1 d R . .
H202 H 1.1574 0.2013 -0.0074 0.030 Uiso 1 1 d R . .
C21 C 1.30584(17) 0.29465(14) -0.02312(12) 0.0293(5) Uani 1 1 d . . .
H211 H 1.3681 0.2979 -0.0529 0.038 Uiso 1 1 d R . .
H212 H 1.3354 0.3033 0.0310 0.038 Uiso 1 1 d R . .
C22 C 1.25749(17) 0.36997(14) -0.04488(13) 0.0321(5) Uani 1 1 d . . .
H221 H 1.2214 0.3577 -0.0975 0.042 Uiso 1 1 d R . .
H222 H 1.1998 0.3698 -0.0117 0.042 Uiso 1 1 d R . .
C23 C 1.34261(19) 0.46286(15) -0.03929(15) 0.0400(6) Uani 1 1 d . . .
H231 H 1.3768 0.4765 0.0137 0.052 Uiso 1 1 d R . .
H232 H 1.4017 0.4628 -0.0711 0.052 Uiso 1 1 d R . .
C24 C 1.2930(2) 0.53622(15) -0.06415(17) 0.0512(7) Uani 1 1 d . . .
H241 H 1.2312 0.5340 -0.0342 0.067 Uiso 1 1 d R . .
H242 H 1.2623 0.5242 -0.1179 0.067 Uiso 1 1 d R . .
C25 C 1.3761(2) 0.63016(17) -0.05476(19) 0.0627(8) Uani 1 1 d . . .
H251 H 1.3401 0.6739 -0.0738 0.075(6) Uiso 1 1 d R . .
H252 H 1.4384 0.6326 -0.0834 0.075(6) Uiso 1 1 d R . .
H253 H 1.4031 0.6442 -0.0011 0.075(6) Uiso 1 1 d R . .
C26 C 1.23616(15) 0.14857(12) 0.27052(11) 0.0193(4) Uani 1 1 d . . .
C27 C 1.27116(15) 0.13084(12) 0.34493(11) 0.0210(4) Uani 1 1 d . . .
H27 H 1.3331 0.1093 0.3537 0.025 Uiso 1 1 d R . .
C28 C 1.21741(15) 0.14450(12) 0.40519(11) 0.0201(4) Uani 1 1 d . . .
H28 H 1.2430 0.1325 0.4548 0.024 Uiso 1 1 d R . .
C29 C 1.12544(15) 0.17564(12) 0.39375(11) 0.0192(4) Uani 1 1 d . . .
C30 C 1.08965(15) 0.19323(12) 0.32042(11) 0.0214(4) Uani 1 1 d . . .
H30 H 1.0270 0.2139 0.3116 0.026 Uiso 1 1 d R . .
C31 C 1.14489(15) 0.18070(13) 0.26048(11) 0.0222(4) Uani 1 1 d . . .
H31 H 1.1201 0.1940 0.2111 0.027 Uiso 1 1 d R . .
C32 C 1.06775(15) 0.19044(12) 0.45700(11) 0.0195(4) Uani 1 1 d . . .
C33 C 0.95026(15) 0.23338(12) 0.51210(11) 0.0208(4) Uani 1 1 d . . .
C34 C 0.85815(15) 0.26894(12) 0.51803(11) 0.0198(4) Uani 1 1 d . . .
C35 C 0.82279(15) 0.27753(12) 0.58897(11) 0.0221(4) Uani 1 1 d . . .
H35 H 0.8617 0.2635 0.6331 0.027 Uiso 1 1 d R . .
C36 C 0.73168(15) 0.30603(12) 0.59493(11) 0.0219(4) Uani 1 1 d . . .
H36 H 0.7093 0.3130 0.6433 0.026 Uiso 1 1 d R . .
C37 C 0.67269(15) 0.32517(12) 0.53000(11) 0.0214(4) Uani 1 1 d . . .
C38 C 0.70895(15) 0.31938(12) 0.45964(11) 0.0227(4) Uani 1 1 d . . .
H38 H 0.6709 0.3346 0.4156 0.027 Uiso 1 1 d R . .
C39 C 0.80132(15) 0.29137(12) 0.45393(11) 0.0215(4) Uani 1 1 d . . .
H39 H 0.8259 0.2873 0.4058 0.026 Uiso 1 1 d R . .
C40 C 0.51199(16) 0.35937(13) 0.47513(12) 0.0253(4) Uani 1 1 d . . .
H401 H 0.4902 0.3045 0.4418 0.033 Uiso 1 1 d R . .
H402 H 0.5533 0.4101 0.4466 0.033 Uiso 1 1 d R . .
C41 C 0.41021(16) 0.37658(14) 0.49964(12) 0.0267(5) Uani 1 1 d . . .
H411 H 0.4330 0.4270 0.5377 0.035 Uiso 1 1 d R . .
H412 H 0.3655 0.3230 0.5235 0.035 Uiso 1 1 d R . .
C42 C 0.34034(16) 0.39941(14) 0.43241(12) 0.0259(5) Uani 1 1 d . . .
H421 H 0.3869 0.4509 0.4071 0.034 Uiso 1 1 d R . .
H422 H 0.3154 0.3477 0.3956 0.034 Uiso 1 1 d R . .
C43 C 0.23884(15) 0.42196(13) 0.45428(12) 0.0239(4) Uani 1 1 d . . .
H431 H 0.1924 0.3705 0.4796 0.031 Uiso 1 1 d R . .
H432 H 0.2639 0.4736 0.4912 0.031 Uiso 1 1 d R . .
C44 C 0.16921(16) 0.44468(13) 0.38758(12) 0.0256(4) Uani 1 1 d . . .
H441 H 0.2165 0.4942 0.3606 0.033 Uiso 1 1 d R . .
H442 H 0.1408 0.3919 0.3519 0.033 Uiso 1 1 d R . .
C45 C 0.07155(16) 0.47194(13) 0.41073(12) 0.0243(4) Uani 1 1 d . . .
H451 H 0.0239 0.4221 0.4371 0.032 Uiso 1 1 d R . .
H452 H 0.1001 0.5241 0.4471 0.032 Uiso 1 1 d R . .
C46 C 0.00137(17) 0.49620(14) 0.34479(12) 0.0286(5) Uani 1 1 d . . .
H461 H -0.0326 0.4426 0.3106 0.037 Uiso 1 1 d R . .
H462 H 0.0499 0.5426 0.3158 0.037 Uiso 1 1 d R . .
C47 C -0.08973(16) 0.53069(14) 0.36938(12) 0.0276(5) Uani 1 1 d . . .
H471 H -0.0561 0.5805 0.4074 0.036 Uiso 1 1 d R . .
H472 H -0.1418 0.4821 0.3943 0.036 Uiso 1 1 d R . .
C48 C -0.15443(18) 0.56339(16) 0.30605(13) 0.0355(5) Uani 1 1 d . . .
H481 H -0.1886 0.5137 0.2680 0.046 Uiso 1 1 d R . .
H482 H -0.1028 0.6122 0.2811 0.046 Uiso 1 1 d R . .
C49 C -0.24543(17) 0.59729(15) 0.33308(13) 0.0337(5) Uani 1 1 d . . .
H491 H -0.2993 0.5473 0.3552 0.044 Uiso 1 1 d R . .
H492 H -0.2117 0.6442 0.3736 0.044 Uiso 1 1 d R . .
C50 C -0.30680(18) 0.63619(16) 0.27108(14) 0.0370(5) Uani 1 1 d . . .
H501 H -0.3738 0.6440 0.2897 0.048 Uiso 1 1 d R . .
H502 H -0.3307 0.5933 0.2269 0.048 Uiso 1 1 d R . .
C51 C -0.23593(19) 0.72499(16) 0.24709(15) 0.0417(6) Uani 1 1 d . . .
H511 H -0.2765 0.7455 0.2049 0.057(4) Uiso 1 1 d R . .
H512 H -0.1678 0.7181 0.2309 0.057(4) Uiso 1 1 d R . .
H513 H -0.2174 0.7691 0.2896 0.057(4) Uiso 1 1 d R . .
C52 C 1.50265(15) 0.12180(12) -0.22769(11) 0.0212(4) Uani 1 1 d . . .
C53 C 1.57870(15) 0.08310(13) -0.25357(11) 0.0218(4) Uani 1 1 d . . .
H53 H 1.6208 0.0578 -0.2184 0.026 Uiso 1 1 d R . .
C54 C 1.59340(15) 0.08133(12) -0.32951(11) 0.0209(4) Uani 1 1 d . . .
H54 H 1.6454 0.0549 -0.3459 0.025 Uiso 1 1 d R . .
C55 C 1.53251(15) 0.11795(12) -0.38215(11) 0.0190(4) Uani 1 1 d . . .
C56 C 1.45719(16) 0.15772(13) -0.35710(11) 0.0241(4) Uani 1 1 d . . .
H56 H 1.4152 0.1832 -0.3922 0.029 Uiso 1 1 d R . .
C57 C 1.44350(17) 0.15954(13) -0.28128(11) 0.0260(5) Uani 1 1 d . . .
H57 H 1.3931 0.1876 -0.2648 0.031 Uiso 1 1 d R . .
C58 C 1.54407(15) 0.11424(12) -0.46282(11) 0.0188(4) Uani 1 1 d . . .
C59 C 1.61612(15) 0.09351(12) -0.56203(10) 0.0187(4) Uani 1 1 d . . .
C60 C 1.69436(15) 0.07039(12) -0.60628(10) 0.0193(4) Uani 1 1 d . . .
C61 C 1.77158(15) 0.03139(12) -0.57376(11) 0.0211(4) Uani 1 1 d . . .
H61 H 1.7755 0.0221 -0.5210 0.025 Uiso 1 1 d R . .
C62 C 1.84301(15) 0.00587(13) -0.61668(11) 0.0222(4) Uani 1 1 d . . .
H62 H 1.8949 -0.0210 -0.5936 0.027 Uiso 1 1 d R . .
C63 C 1.83715(15) 0.02027(12) -0.69421(11) 0.0211(4) Uani 1 1 d . . .
C64 C 1.76084(16) 0.06083(13) -0.72725(11) 0.0246(4) Uani 1 1 d . . .
H64 H 1.7578 0.0716 -0.7797 0.030 Uiso 1 1 d R . .
C65 C 1.69034(16) 0.08525(13) -0.68395(11) 0.0232(4) Uani 1 1 d . . .
H65 H 1.6385 0.1123 -0.7069 0.028 Uiso 1 1 d R . .
C66 C 1.97688(16) -0.04965(13) -0.71291(11) 0.0240(4) Uani 1 1 d . . .
H661 H 1.9397 -0.0997 -0.6821 0.031 Uiso 1 1 d R . .
H662 H 2.0392 -0.0076 -0.6805 0.031 Uiso 1 1 d R . .
C67 C 2.01865(17) -0.08448(14) -0.77980(11) 0.0265(5) Uani 1 1 d . . .
H671 H 2.0669 -0.0334 -0.8045 0.034 Uiso 1 1 d R . .
H672 H 1.9550 -0.1153 -0.8171 0.034 Uiso 1 1 d R . .
C68 C 2.08328(17) -0.14933(15) -0.75706(12) 0.0310(5) Uani 1 1 d . . .
H681 H 2.0417 -0.1926 -0.7225 0.040 Uiso 1 1 d R . .
H682 H 2.1551 -0.1154 -0.7290 0.040 Uiso 1 1 d R . .
C69 C 2.1045(2) -0.20065(16) -0.82424(14) 0.0410(6) Uani 1 1 d . B .
H691 H 2.0342 -0.2261 -0.8572 0.053 Uiso 1 1 d R . .
H692 H 2.1569 -0.1585 -0.8541 0.053 Uiso 1 1 d R . .
C70 C 2.1501(3) -0.27653(17) -0.80178(17) 0.0594(8) Uani 1 1 d D . .
H701 H 2.0975 -0.3161 -0.7657 0.077 Uiso 1 1 d R B .
H702 H 2.2349 -0.2546 -0.7831 0.077 Uiso 1 1 d R . .
C71A C 2.1357(4) -0.3384(3) -0.8806(3) 0.0408(11) Uiso 0.55 1 d PD B 1
H711 H 2.0609 -0.3471 -0.9071 0.053 Uiso 0.55 1 d PR B 1
H712 H 2.1902 -0.3060 -0.9143 0.053 Uiso 0.55 1 d PR B 1
C72A C 2.1507(4) -0.4295(3) -0.8651(3) 0.0419(11) Uiso 0.55 1 d PD B 1
H721 H 2.1345 -0.4647 -0.9137 0.055 Uiso 0.55 1 d PR B 1
H722 H 2.0954 -0.4614 -0.8317 0.055 Uiso 0.55 1 d PR B 1
C73A C 2.2671(4) -0.4273(3) -0.8287(3) 0.0413(11) Uiso 0.55 1 d PD B 1
H731 H 2.3235 -0.3932 -0.8604 0.054 Uiso 0.55 1 d PR B 1
H732 H 2.2820 -0.3960 -0.7783 0.054 Uiso 0.55 1 d PR B 1
C74A C 2.2778(4) -0.5200(3) -0.8193(3) 0.0417(12) Uiso 0.55 1 d PD B 1
H741 H 2.2259 -0.5513 -0.7836 0.054 Uiso 0.55 1 d PR B 1
H742 H 2.2533 -0.5530 -0.8689 0.054 Uiso 0.55 1 d PR B 1
C71B C 2.1894(5) -0.3314(3) -0.8506(3) 0.0397(13) Uiso 0.45 1 d PD B 2
H713 H 2.2495 -0.2908 -0.8759 0.052 Uiso 0.45 1 d PR B 2
H714 H 2.1280 -0.3595 -0.8903 0.052 Uiso 0.45 1 d PR B 2
C72B C 2.2317(5) -0.4059(4) -0.8173(3) 0.0432(14) Uiso 0.45 1 d PD B 2
H723 H 2.3036 -0.3780 -0.7868 0.056 Uiso 0.45 1 d PR B 2
H724 H 2.1793 -0.4394 -0.7828 0.056 Uiso 0.45 1 d PR B 2
C73B C 2.2464(5) -0.4699(4) -0.8739(3) 0.0502(15) Uiso 0.45 1 d PD B 2
H733 H 2.3073 -0.4381 -0.9032 0.065 Uiso 0.45 1 d PR B 2
H734 H 2.1781 -0.4903 -0.9097 0.065 Uiso 0.45 1 d PR B 2
C74B C 2.2716(5) -0.5515(4) -0.8409(4) 0.0453(15) Uiso 0.45 1 d PD B 2
H743 H 2.2692 -0.5943 -0.8827 0.059 Uiso 0.45 1 d PR B 2
H744 H 2.2140 -0.5814 -0.8084 0.059 Uiso 0.45 1 d PR B 2
C75 C 2.3895(2) -0.52780(17) -0.79291(16) 0.0484(7) Uani 1 1 d D . .
H751 H 2.4430 -0.4948 -0.8325 0.063 Uiso 1 1 d R B .
H752 H 2.4060 -0.4938 -0.7423 0.063 Uiso 1 1 d R . .
C76 C 2.4054(2) -0.61855(16) -0.77824(14) 0.0446(6) Uani 1 1 d . B .
H761 H 2.3496 -0.6517 -0.7457 0.058 Uiso 1 1 d R . .
H762 H 2.3916 -0.6528 -0.8272 0.058 Uiso 1 1 d R . .
C77 C 2.5191(2) -0.61325(18) -0.74134(17) 0.0552(7) Uani 1 1 d . . .
H771 H 2.5223 -0.6739 -0.7319 0.078(6) Uiso 1 1 d R B .
H772 H 2.5341 -0.5785 -0.6933 0.078(6) Uiso 1 1 d R . .
H773 H 2.5746 -0.5843 -0.7748 0.078(6) Uiso 1 1 d R . .
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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 0.00 0.0200
0.00 -1.00 0.00 0.0200
0.00 0.00 -1.00 0.1800
0.00 0.00 1.00 0.1800
1.00 1.00 0.00 0.1200
-1.00 -1.00 0.00 0.1200
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
C33 O1 C32 102.74(14) . . ?
C59 O2 C58 102.51(14) . . ?
C37 O3 C40 116.86(15) . . ?
C63 O4 C66 117.91(15) . . ?
C32 N1 N2 106.07(16) . . ?
C33 N2 N1 106.36(16) . . ?
C58 N3 N4 106.24(15) . . ?
C59 N4 N3 106.29(15) . . ?
C10 C1 C2 120.61(17) . . ?
C1 C2 C3 118.48(17) . . ?
C1 C2 C26 120.73(16) . . ?
C3 C2 C26 120.70(17) . . ?
C4 C3 C2 121.08(18) . . ?
C3 C4 C11 119.68(18) . . ?
C6 C5 C12 118.85(18) . . ?
C5 C6 C7 121.83(17) . . ?
C6 C7 C8 118.52(17) . . ?
C6 C7 C52 121.15(17) . . ?
C8 C7 C52 120.33(17) . . ?
C13 C8 C7 119.75(18) . . ?
C10 C9 C13 100.85(15) . . ?
C10 C9 C20 111.48(16) . . ?
C13 C9 C20 112.35(15) . . ?
C10 C9 C14 112.87(16) . . ?
C13 C9 C14 111.22(15) . . ?
C20 C9 C14 108.04(15) . . ?
C1 C10 C11 120.28(17) . . ?
C1 C10 C9 128.56(17) . . ?
C11 C10 C9 111.10(16) . . ?
C4 C11 C10 119.83(17) . . ?
C4 C11 C12 131.90(17) . . ?
C10 C11 C12 108.26(16) . . ?
C5 C12 C13 120.51(18) . . ?
C5 C12 C11 130.90(18) . . ?
C13 C12 C11 108.59(16) . . ?
C8 C13 C12 120.52(17) . . ?
C8 C13 C9 128.27(17) . . ?
C12 C13 C9 111.20(16) . . ?
C15 C14 C9 116.39(16) . . ?
C14 C15 C16 113.03(18) . . ?
C15 C16 C17A 115.9(2) . . ?
C15 C16 C17B 113.0(2) . . ?
C17A C16 C17B 28.1(2) . . ?
C18A C17A C16 114.1(4) . . ?
C17A C18A C19A 112.9(5) . . ?
C18B C17B C16 113.3(4) . . ?
C19B C18B C17B 112.3(5) . . ?
C21 C20 C9 116.96(16) . . ?
C20 C21 C22 112.27(17) . . ?
C21 C22 C23 114.06(18) . . ?
C24 C23 C22 113.0(2) . . ?
C23 C24 C25 113.5(2) . . ?
C31 C26 C27 117.23(17) . . ?
C31 C26 C2 120.50(17) . . ?
C27 C26 C2 122.24(17) . . ?
C28 C27 C26 121.27(17) . . ?
C27 C28 C29 120.55(18) . . ?
C30 C29 C28 118.83(17) . . ?
C30 C29 C32 120.01(17) . . ?
C28 C29 C32 121.16(17) . . ?
C31 C30 C29 120.31(17) . . ?
C30 C31 C26 121.78(18) . . ?
N1 C32 O1 112.48(16) . . ?
N1 C32 C29 129.75(17) . . ?
O1 C32 C29 117.77(16) . . ?
N2 C33 O1 112.35(16) . . ?
N2 C33 C34 129.37(18) . . ?
O1 C33 C34 118.25(17) . . ?
C39 C34 C35 119.00(17) . . ?
C39 C34 C33 121.19(17) . . ?
C35 C34 C33 119.75(18) . . ?
C36 C35 C34 120.39(18) . . ?
C35 C36 C37 120.18(18) . . ?
O3 C37 C38 124.46(18) . . ?
O3 C37 C36 115.70(17) . . ?
C38 C37 C36 119.84(17) . . ?
C37 C38 C39 119.76(18) . . ?
C38 C39 C34 120.75(18) . . ?
O3 C40 C41 108.59(16) . . ?
C40 C41 C42 111.09(17) . . ?
C41 C42 C43 113.54(17) . . ?
C44 C43 C42 113.67(17) . . ?
C43 C44 C45 113.12(17) . . ?
C46 C45 C44 114.02(17) . . ?
C47 C46 C45 113.38(17) . . ?
C48 C47 C46 114.84(18) . . ?
C47 C48 C49 113.22(18) . . ?
C50 C49 C48 114.13(19) . . ?
C51 C50 C49 112.00(19) . . ?
C57 C52 C53 117.60(18) . . ?
C57 C52 C7 120.89(17) . . ?
C53 C52 C7 121.50(18) . . ?
C54 C53 C52 121.00(18) . . ?
C53 C54 C55 120.56(17) . . ?
C54 C55 C56 119.13(18) . . ?
C54 C55 C58 121.48(17) . . ?
C56 C55 C58 119.39(17) . . ?
C57 C56 C55 119.89(19) . . ?
C56 C57 C52 121.81(18) . . ?
N3 C58 O2 112.57(16) . . ?
N3 C58 C55 129.04(17) . . ?
O2 C58 C55 118.39(16) . . ?
N4 C59 O2 112.38(16) . . ?
N4 C59 C60 129.20(17) . . ?
O2 C59 C60 118.41(16) . . ?
C61 C60 C65 118.72(17) . . ?
C61 C60 C59 121.62(17) . . ?
C65 C60 C59 119.64(17) . . ?
C62 C61 C60 121.56(18) . . ?
C61 C62 C63 119.02(18) . . ?
O4 C63 C62 124.88(17) . . ?
O4 C63 C64 115.27(17) . . ?
C62 C63 C64 119.84(17) . . ?
C65 C64 C63 120.35(18) . . ?
C64 C65 C60 120.50(18) . . ?
O4 C66 C67 107.05(16) . . ?
C66 C67 C68 112.53(17) . . ?
C67 C68 C69 113.44(18) . . ?
C70 C69 C68 113.7(2) . . ?
C71B C70 C69 127.4(3) . . ?
C71B C70 C71A 29.0(2) . . ?
C69 C70 C71A 105.5(3) . . ?
C72A C71A C70 112.3(3) . . ?
C71A C72A C73A 115.3(4) . . ?
C74A C73A C72A 112.3(4) . . ?
C75 C74A C73A 118.0(4) . . ?
C70 C71B C72B 119.8(5) . . ?
C73B C72B C71B 114.8(5) . . ?
C72B C73B C74B 114.6(5) . . ?
C73B C74B C75 113.1(5) . . ?
C74A C75 C76 120.9(3) . . ?
C74A C75 C74B 22.3(3) . . ?
C76 C75 C74B 103.9(3) . . ?
C77 C76 C75 113.8(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
O1 C33 1.365(2) . ?
O1 C32 1.366(2) . ?
O2 C59 1.367(2) . ?
O2 C58 1.369(2) . ?
O3 C37 1.363(2) . ?
O3 C40 1.437(2) . ?
O4 C63 1.362(2) . ?
O4 C66 1.442(2) . ?
N1 C32 1.289(2) . ?
N1 N2 1.414(2) . ?
N2 C33 1.288(3) . ?
N3 C58 1.289(2) . ?
N3 N4 1.410(2) . ?
N4 C59 1.294(2) . ?
C1 C10 1.382(3) . ?
C1 C2 1.403(3) . ?
C2 C3 1.409(3) . ?
C2 C26 1.486(3) . ?
C3 C4 1.387(3) . ?
C4 C11 1.393(3) . ?
C5 C6 1.381(3) . ?
C5 C12 1.391(3) . ?
C6 C7 1.402(3) . ?
C7 C8 1.409(3) . ?
C7 C52 1.485(3) . ?
C8 C13 1.385(3) . ?
C9 C10 1.523(3) . ?
C9 C13 1.526(2) . ?
C9 C20 1.542(3) . ?
C9 C14 1.547(3) . ?
C10 C11 1.404(3) . ?
C11 C12 1.465(3) . ?
C12 C13 1.395(3) . ?
C14 C15 1.505(3) . ?
C15 C16 1.517(3) . ?
C16 C17A 1.527(5) . ?
C16 C17B 1.542(5) . ?
C17A C18A 1.523(7) . ?
C18A C19A 1.526(7) . ?
C17B C18B 1.526(7) . ?
C18B C19B 1.510(7) . ?
C20 C21 1.520(3) . ?
C21 C22 1.523(3) . ?
C22 C23 1.523(3) . ?
C23 C24 1.518(3) . ?
C24 C25 1.525(3) . ?
C26 C31 1.397(3) . ?
C26 C27 1.407(3) . ?
C27 C28 1.376(3) . ?
C28 C29 1.397(3) . ?
C29 C30 1.392(3) . ?
C29 C32 1.457(3) . ?
C30 C31 1.379(3) . ?
C33 C34 1.456(3) . ?
C34 C39 1.391(3) . ?
C34 C35 1.399(3) . ?
C35 C36 1.377(3) . ?
C36 C37 1.395(3) . ?
C37 C38 1.387(3) . ?
C38 C39 1.387(3) . ?
C40 C41 1.507(3) . ?
C41 C42 1.525(3) . ?
C42 C43 1.525(3) . ?
C43 C44 1.516(3) . ?
C44 C45 1.524(3) . ?
C45 C46 1.521(3) . ?
C46 C47 1.520(3) . ?
C47 C48 1.510(3) . ?
C48 C49 1.529(3) . ?
C49 C50 1.522(3) . ?
C50 C51 1.503(3) . ?
C52 C57 1.398(3) . ?
C52 C53 1.400(3) . ?
C53 C54 1.381(3) . ?
C54 C55 1.391(3) . ?
C55 C56 1.397(3) . ?
C55 C58 1.457(3) . ?
C56 C57 1.376(3) . ?
C59 C60 1.455(3) . ?
C60 C61 1.388(3) . ?
C60 C65 1.399(3) . ?
C61 C62 1.388(3) . ?
C62 C63 1.395(3) . ?
C63 C64 1.399(3) . ?
C64 C65 1.374(3) . ?
C66 C67 1.511(3) . ?
C67 C68 1.522(3) . ?
C68 C69 1.523(3) . ?
C69 C70 1.512(3) . ?
C70 C71B 1.439(5) . ?
C70 C71A 1.656(5) . ?
C71A C72A 1.520(6) . ?
C72A C73A 1.546(6) . ?
C73A C74A 1.507(6) . ?
C74A C75 1.493(5) . ?
C71B C72B 1.527(7) . ?
C72B C73B 1.476(7) . ?
C73B C74B 1.518(7) . ?
C74B C75 1.585(6) . ?
C75 C76 1.516(3) . ?
C76 C77 1.505(4) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C25 C24 C23 C22 176.9(2) . . . . ?
C24 C23 C22 C21 177.8(2) . . . . ?
C23 C22 C21 C20 -174.98(18) . . . . ?
C22 C21 C20 C9 -179.03(17) . . . . ?
C21 C20 C9 C14 -174.09(16) . . . . ?
C20 C9 C14 C15 176.68(17) . . . . ?
C9 C14 C15 C16 -171.01(18) . . . . ?
C14 C15 C16 C17A 160.2(3) . . . . ?
C15 C16 C17A C18A 180.0(4) . . . . ?
C16 C17A C18A C19A -173.7(5) . . . . ?
C14 C15 C16 C17B -169.1(3) . . . . ?
C15 C16 C17B C18B -170.2(4) . . . . ?
C16 C17B C18B C19B 72.9(6) . . . . ?
C10 C9 C20 C21 61.3(2) . . . . ?
C10 C9 C14 C15 -59.6(2) . . . . ?
C3 C2 C26 C27 -22.8(3) . . . . ?
C2 C26 C27 C28 178.28(17) . . . . ?
C26 C27 C28 C29 0.7(3) . . . . ?
C27 C28 C29 C32 -179.98(17) . . . . ?
C28 C29 C32 O1 174.27(16) . . . . ?
C29 C32 O1 C33 -179.46(16) . . . . ?
C32 O1 C33 C34 -178.19(16) . . . . ?
O1 C33 C34 C35 -178.02(16) . . . . ?
C33 C34 C35 C36 -176.14(17) . . . . ?
C34 C35 C36 C37 1.1(3) . . . . ?
C35 C36 C37 O3 176.70(16) . . . . ?
C36 C37 O3 C41 -167.1(2) . . . . ?
C37 O3 C41 C42 -20.6(4) . . . . ?
O3 C41 C42 C43 -170.75(19) . . . . ?
C41 C42 C43 C44 180.00(17) . . . . ?
C42 C43 C44 C45 -176.92(16) . . . . ?
C43 C44 C45 C46 179.25(17) . . . . ?
C44 C45 C46 C47 -175.15(17) . . . . ?
C45 C46 C47 C48 174.68(18) . . . . ?
C46 C47 C48 C49 179.86(19) . . . . ?
C47 C48 C49 C50 176.24(19) . . . . ?
C48 C49 C50 C51 -71.3(3) . . . . ?
C49 C50 C51 C52 59.20(18) . . . . ?
C6 C7 C52 C53 30.6(3) . . . . ?
C7 C52 C53 C54 178.50(17) . . . . ?
C52 C53 C54 C55 -0.1(3) . . . . ?
C53 C54 C55 C58 -177.99(17) . . . . ?
C54 C55 C58 O2 -11.6(3) . . . . ?
C55 C58 O2 C59 -179.43(15) . . . . ?
C58 O2 C59 C60 -179.99(15) . . . . ?
O2 C59 C60 C61 9.6(3) . . . . ?
C59 C60 C61 C62 177.21(17) . . . . ?
C60 C61 C62 C63 0.3(3) . . . . ?
C61 C62 C63 O4 -177.82(17) . . . . ?
C62 C63 O4 C66 1.1(3) . . . . ?
C63 O4 C66 C67 169.36(16) . . . . ?
O4 C66 C67 C68 -168.84(16) . . . . ?
C66 C67 C68 C69 167.46(18) . . . . ?
C67 C68 C69 C70 -169.7(2) . . . . ?
C68 C69 C70 C71A 165.5(2) . . . . ?
C69 C70 C71A C72A -165.8(3) . . . . ?
C70 C71A C72A C73A -63.5(5) . . . . ?
C71A C72A C73A C74A -176.6(4) . . . . ?
C72A C73A C74A C75 173.2(4) . . . . ?
C73A C74A C75 C76 176.7(3) . . . . ?
C74A C75 C76 C77 -171.6(3) . . . . ?
C68 C69 C70 C71B -173.1(4) . . . . ?
C69 C70 C71B C72B -179.4(4) . . . . ?
C70 C71B C72B C73B 167.1(5) . . . . ?
C71B C72B C73B C74B -171.2(5) . . . . ?
C72B C73B C74B C75 -67.7(7) . . . . ?
C73B C74B C75 C76 -170.0(4) . . . . ?
C74B C75 C76 C77 172.8(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101372211
