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#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/45/1554569.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.
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data_1554569
loop_
_publ_author_name
'Lee, Chaeeun'
'Lee, Hyemi'
'Lee, Seungwon'
'Jeon, Hae-Geun'
'Jeong, Kyu-Sung'
_publ_section_title
;
 Encapsulation of dihydrogenphosphate ions as a cyclic dimer to the
 cavities of site-specifically modified indolocarbazole-pyridine foldamers
;
_journal_issue                   3
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              299
_journal_paper_doi               10.1039/C8QO01307A
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         '2(H2 O4 P), C140 H127 N11 O2, 2(C16 H36 N)'
_chemical_formula_sum            'C172 H203 N13 O10 P2'
_chemical_formula_weight         2674.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2018-11-25 deposited with the CCDC.
2018-12-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.17(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.469(4)
_cell_length_b                   29.096(6)
_cell_length_c                   28.543(6)
_cell_measurement_reflns_used    394308
_cell_measurement_temperature    100
_cell_measurement_theta_max      33.749
_cell_measurement_theta_min      0.401
_cell_volume                     17757(6)
_computing_cell_refinement       'HKL3000sm (Otwinowski & Minor, 1997)'
_computing_data_collection       'PAL BL2D-SMDC Program (Shin et. al, 2016)'
_computing_data_reduction        'HKL3000sm (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_reflns_av_R_equivalents  0.0958
_diffrn_reflns_av_unetI/netI     0.1684
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            45276
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         28.500
_diffrn_reflns_theta_min         1.317
_diffrn_source                   'PLSII 2D bending magnet'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_process_details   'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.000
_exptl_crystal_description       block
_exptl_crystal_F_000             5744
_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.026
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.00016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   0.828
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     972
_refine_ls_number_reflns         22866
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      0.842
_refine_ls_R_factor_all          0.1761
_refine_ls_R_factor_gt           0.0712
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0792P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1519
_refine_ls_wR_factor_ref         0.1857
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8173
_reflns_number_total             22866
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8qo01307a2.cif
_cod_data_source_block           ce10_merge_a
_cod_database_code               1554569
_shelx_shelxl_version_number     2017/1
_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_max   0.998
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C62-C65 \\sim C62-C164
 with sigma of 0.02
 C62-C64 \\sim C62-C163
 with sigma of 0.02
 C62-C63 \\sim C62-C165
 with sigma of 0.02
 C66-C69 \\sim C66-C169
 with sigma of 0.02
 C66-C67 \\sim C66-C167
 with sigma of 0.02
 C66-C68 \\sim C66-C168
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C164) \\sim Ueq, Uanis(C64) \\sim Ueq, Uanis(C163) \\sim Ueq, Uanis(C63)
\\sim Ueq, Uanis(C165) \\sim Ueq, Uanis(C65) \\sim Ueq: with sigma of 0.1 and
sigma for terminal atoms of 0.01
4. Others
 Sof(C163)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(C164)=Sof(H16G)=Sof(H16H)=
 Sof(H16I)=Sof(C165)=Sof(H16D)=Sof(H16E)=Sof(H16F)=1-FVAR(1)
 Sof(C63)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=Sof(C64)=Sof(H2AD)=Sof(H2AE)=Sof(H2AF)=
 Sof(C65)=Sof(H02U)=Sof(H02S)=Sof(H02T)=FVAR(1)
 Sof(C167)=Sof(H16P)=Sof(H16Q)=Sof(H16R)=Sof(C168)=Sof(H16J)=Sof(H16K)=
 Sof(H16L)=Sof(C169)=Sof(H16M)=Sof(H16N)=Sof(H16O)=1-FVAR(2)
 Sof(C67)=Sof(H02Y)=Sof(HK)=Sof(HL)=Sof(C68)=Sof(H1AB)=Sof(H1AC)=Sof(H1AD)=
 Sof(C69)=Sof(H02V)=Sof(H02W)=Sof(H02X)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C84(H84A,H84B), C85(H85A,H85B), C86(H86A,H86B), C88(H88A,H88B), C89(H89A,
 H89B), C90(H90A,H90B), C92(H92B,H92A), C93(H93A,H93B), C94(H94A,H94B),
 C96(H96A,H96B), C97(H97A,H97B), C98(H98A,H98B)
5.b Aromatic/amide H refined with riding coordinates:
 N3(H3), N6(H6), N23(H23), N26(H26), N48(H48), C9(H9), C11(H11), C14(H14),
 C15(H15), C18(H18), C20(H20), C29(H29), C31(H31), C34(H34), C35(H35), C38(H38),
  C40(H40), C44(H44), C45(H45), C46(H46), C49(H49)
5.c Idealised Me refined as rotating group:
 C60(H60A,H60B,H60C), C61(H61A,H61B,H61C), C71(H71A,H71B,H71C), C72(H72A,H72B,
 H72C), C73(H73A,H73B,H73C), C75(H75A,H75B,H75C), C76(H76A,H76B,H76C), C77(H77A,
 H77B,H77C), C163(H16A,H16B,H16C), C164(H16G,H16H,H16I), C165(H16D,H16E,H16F),
 C167(H16P,H16Q,H16R), C168(H16J,H16K,H16L), C169(H16M,H16N,H16O), C87(H87A,
 H87B,H87C), C91(H91A,H91B,H91C), C95(H95A,H95B,H95C), C99(H99A,H99B,H99C),
 C63(H3AA,H3AB,H3AC), C64(H2AD,H2AE,H2AF), C65(H02U,H02S,H02T), C67(H02Y,HK,HL),
  C68(H1AB,H1AC,H1AD), C69(H02V,H02W,H02X)
5.d Idealised tetrahedral OH refined as rotating group:
 O80(H80), O81(H81), O59(H59)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
P78 P 0.51355(4) 0.53362(2) 0.32142(3) 0.0388(2) Uani 1 1 d . . . . .
O79 O 0.52982(10) 0.56040(6) 0.36516(7) 0.0465(5) Uani 1 1 d . . . . .
O80 O 0.45779(10) 0.55973(6) 0.29271(7) 0.0427(5) Uani 1 1 d . . . . .
H80 H 0.448325 0.546173 0.267897 0.064 Uiso 1 1 calc GR . . . .
O81 O 0.48228(10) 0.48622(6) 0.33267(8) 0.0479(5) Uani 1 1 d . . . . .
H81 H 0.509491 0.466563 0.337451 0.072 Uiso 1 1 calc GR . . . .
O82 O 0.56659(9) 0.52569(6) 0.29048(6) 0.0418(5) Uani 1 1 d . . . . .
O59 O 0.35296(11) 0.56443(6) 0.34626(8) 0.0492(6) Uani 1 1 d . . . . .
H59 H 0.384845 0.564318 0.332459 0.074 Uiso 1 1 calc GR . . . .
N3 N 0.53805(12) 0.64974(7) 0.40280(8) 0.0427(6) Uani 1 1 d . . . . .
H3 H 0.519452 0.625526 0.391303 0.051 Uiso 1 1 calc R . . . .
N6 N 0.63578(12) 0.56972(8) 0.42299(8) 0.0427(6) Uani 1 1 d . . . . .
H6 H 0.603796 0.556435 0.408554 0.051 Uiso 1 1 calc R . . . .
N23 N 0.33392(12) 0.45460(7) 0.21724(8) 0.0413(6) Uani 1 1 d . . . . .
H23 H 0.368248 0.468104 0.227120 0.050 Uiso 1 1 calc R . . . .
N26 N 0.30819(12) 0.55944(7) 0.18413(8) 0.0396(6) Uani 1 1 d . . . . .
H26 H 0.346273 0.560138 0.196373 0.047 Uiso 1 1 calc R . . . .
N42 N 0.55041(13) 0.40815(7) 0.34535(8) 0.0392(6) Uani 1 1 d . . . . .
N48 N 0.500000 0.66247(11) 0.250000 0.0461(9) Uani 1 2 d S T P . .
H48 H 0.500001 0.632914 0.249999 0.055 Uiso 1 2 calc RS T P . .
C1 C 0.45318(17) 0.70765(10) 0.38685(11) 0.0487(8) Uani 1 1 d . . . . .
C2 C 0.51289(16) 0.69346(9) 0.40270(10) 0.0438(8) Uani 1 1 d . . . . .
C4 C 0.59738(15) 0.65153(9) 0.42422(10) 0.0398(7) Uani 1 1 d . . . . .
C5 C 0.64108(15) 0.61646(9) 0.43393(10) 0.0399(7) Uani 1 1 d . . . . .
C7 C 0.69067(15) 0.54888(10) 0.43938(10) 0.0409(7) Uani 1 1 d . . . . .
C8 C 0.70780(15) 0.50252(10) 0.43771(10) 0.0427(7) Uani 1 1 d . . . . .
C9 C 0.76589(16) 0.49079(11) 0.46019(10) 0.0474(8) Uani 1 1 d . . . . .
H9 H 0.777862 0.460089 0.459761 0.057 Uiso 1 1 calc R . . . .
C10 C 0.80750(16) 0.52213(11) 0.48341(10) 0.0493(8) Uani 1 1 d . . . . .
C11 C 0.78896(15) 0.56829(11) 0.48301(10) 0.0460(8) Uani 1 1 d . . . . .
H11 H 0.815794 0.590241 0.497363 0.055 Uiso 1 1 calc R . . . .
C12 C 0.73153(15) 0.58185(10) 0.46170(10) 0.0442(8) Uani 1 1 d . . . . .
C13 C 0.69866(15) 0.62558(10) 0.45748(10) 0.0440(8) Uani 1 1 d . . . . .
C14 C 0.71385(16) 0.67110(10) 0.47287(10) 0.0463(8) Uani 1 1 d . . . . .
H14 H 0.752351 0.677442 0.489192 0.056 Uiso 1 1 calc R . . . .
C15 C 0.67076(16) 0.70553(10) 0.46322(10) 0.0491(8) Uani 1 1 d . . . . .
H15 H 0.680556 0.735375 0.472957 0.059 Uiso 1 1 calc R . . . .
C16 C 0.61233(16) 0.69652(10) 0.43899(10) 0.0450(8) Uani 1 1 d . . . . .
C17 C 0.55691(16) 0.72367(10) 0.42448(10) 0.0468(8) Uani 1 1 d . . . . .
C18 C 0.54049(18) 0.76994(10) 0.43067(11) 0.0561(9) Uani 1 1 d . . . . .
H18 H 0.569367 0.790149 0.445628 0.067 Uiso 1 1 calc R . . . .
C19 C 0.48160(19) 0.78544(10) 0.41459(12) 0.0624(10) Uani 1 1 d . . . . .
C20 C 0.43889(18) 0.75395(10) 0.39308(11) 0.0574(9) Uani 1 1 d . . . . .
H20 H 0.399135 0.764316 0.382434 0.069 Uiso 1 1 calc R . . . .
C21 C 0.35457(16) 0.37330(9) 0.24700(10) 0.0442(8) Uani 1 1 d . . . . .
C22 C 0.31994(16) 0.40843(9) 0.22287(10) 0.0427(8) Uani 1 1 d . . . . .
C24 C 0.28213(15) 0.47502(9) 0.19267(10) 0.0411(7) Uani 1 1 d . . . . .
C25 C 0.27030(15) 0.52104(9) 0.17892(10) 0.0398(7) Uani 1 1 d . . . . .
C27 C 0.27372(15) 0.59642(9) 0.16607(10) 0.0388(7) Uani 1 1 d . . . . .
C28 C 0.29146(15) 0.64279(9) 0.16369(10) 0.0391(7) Uani 1 1 d . . . . .
C29 C 0.24604(16) 0.67286(10) 0.14364(10) 0.0450(8) Uani 1 1 d . . . . .
H29 H 0.256806 0.703685 0.141329 0.054 Uiso 1 1 calc R . . . .
C30 C 0.18586(15) 0.65998(10) 0.12690(10) 0.0427(7) Uani 1 1 d . . . . .
C31 C 0.16992(16) 0.61379(10) 0.13096(10) 0.0471(8) Uani 1 1 d . . . . .
H31 H 0.129615 0.604078 0.121004 0.057 Uiso 1 1 calc R . . . .
C32 C 0.21415(15) 0.58190(9) 0.14992(10) 0.0411(7) Uani 1 1 d . . . . .
C33 C 0.21144(15) 0.53256(10) 0.15832(10) 0.0420(7) Uani 1 1 d . . . . .
C34 C 0.16427(16) 0.49985(10) 0.14865(11) 0.0490(8) Uani 1 1 d . . . . .
H34 H 0.125458 0.508549 0.134285 0.059 Uiso 1 1 calc R . . . .
C35 C 0.17594(16) 0.45475(10) 0.16060(10) 0.0486(8) Uani 1 1 d . . . . .
H35 H 0.145172 0.432538 0.154313 0.058 Uiso 1 1 calc R . . . .
C36 C 0.23481(16) 0.44258(10) 0.18240(10) 0.0456(8) Uani 1 1 d . . . . .
C37 C 0.26008(16) 0.39925(9) 0.20113(10) 0.0452(8) Uani 1 1 d . . . . .
C38 C 0.23596(18) 0.35487(10) 0.19971(11) 0.0560(9) Uani 1 1 d . . . . .
H38 H 0.196687 0.349282 0.184251 0.067 Uiso 1 1 calc R . . . .
C39 C 0.26990(19) 0.31889(10) 0.22114(11) 0.0551(9) Uani 1 1 d . . . . .
C40 C 0.32759(18) 0.32910(10) 0.24469(11) 0.0530(9) Uani 1 1 d . . . . .
H40 H 0.349937 0.305222 0.259947 0.064 Uiso 1 1 calc R . . . .
C41 C 0.60459(16) 0.40093(9) 0.37140(10) 0.0417(7) Uani 1 1 d . . . . .
C43 C 0.52141(17) 0.37151(9) 0.32399(10) 0.0457(8) Uani 1 1 d . . . . .
C44 C 0.54582(19) 0.32668(10) 0.32984(11) 0.0571(10) Uani 1 1 d . . . . .
H44 H 0.524799 0.301879 0.315209 0.068 Uiso 1 1 calc R . . . .
C45 C 0.60052(18) 0.32001(10) 0.35715(11) 0.0556(9) Uani 1 1 d . . . . .
H45 H 0.617299 0.290676 0.361326 0.067 Uiso 1 1 calc R . . . .
C46 C 0.63049(17) 0.35733(10) 0.37842(11) 0.0525(9) Uani 1 1 d . . . . .
H46 H 0.667726 0.353475 0.397315 0.063 Uiso 1 1 calc R . . . .
C47 C 0.45451(15) 0.68878(9) 0.22757(11) 0.0444(8) Uani 1 1 d . . . . .
C49 C 0.47209(18) 0.73348(11) 0.23570(15) 0.0823(13) Uani 1 1 d . . . . .
H49 H 0.450424 0.759345 0.224085 0.099 Uiso 1 1 calc R . . . .
C50 C 0.37097(15) 0.64494(9) 0.35650(10) 0.0433(8) Uani 1 1 d . . . . .
C51 C 0.40665(16) 0.67494(9) 0.36834(10) 0.0458(8) Uani 1 1 d . . . . .
C52 C 0.66769(15) 0.46871(10) 0.41437(10) 0.0439(7) Uani 1 1 d . . . . .
C53 C 0.63602(15) 0.43937(10) 0.39466(10) 0.0431(7) Uani 1 1 d . . . . .
C54 C 0.46303(18) 0.37842(9) 0.29656(11) 0.0430(8) Uani 1 1 d . . . . .
C55 C 0.41414(17) 0.37890(9) 0.27293(11) 0.0414(8) Uani 1 1 d . . . . .
C56 C 0.35093(16) 0.65831(9) 0.18306(10) 0.0386(7) Uani 1 1 d . . . . .
C57 C 0.39956(16) 0.67089(9) 0.20265(10) 0.0413(7) Uani 1 1 d . . . . .
C58 C 0.32451(15) 0.60914(9) 0.34232(11) 0.0439(8) Uani 1 1 d . . . . .
C60 C 0.29708(18) 0.61717(10) 0.29228(11) 0.0584(10) Uani 1 1 d . . . . .
H60A H 0.329811 0.616007 0.271502 0.088 Uiso 1 1 calc GR . . . .
H60B H 0.277370 0.646804 0.290032 0.088 Uiso 1 1 calc GR . . . .
H60C H 0.266661 0.593803 0.283545 0.088 Uiso 1 1 calc GR . . . .
C61 C 0.27407(17) 0.60863(11) 0.37654(12) 0.0606(10) Uani 1 1 d . . . . .
H61A H 0.242619 0.586459 0.366329 0.091 Uiso 1 1 calc GR . . . .
H61B H 0.255356 0.638547 0.377499 0.091 Uiso 1 1 calc GR . . . .
H61C H 0.292419 0.600579 0.407358 0.091 Uiso 1 1 calc GR . . . .
C62 C 0.4633(2) 0.83604(11) 0.42127(17) 0.0899(15) Uani 1 1 d D . . . .
C66 C 0.86970(16) 0.50652(13) 0.50701(12) 0.0592(10) Uani 1 1 d D . . . .
C70 C 0.2447(2) 0.26962(11) 0.21656(13) 0.0712(12) Uani 1 1 d . . . . .
C71 C 0.2472(2) 0.25346(11) 0.16565(12) 0.0712(11) Uani 1 1 d . . . . .
H71A H 0.225539 0.275119 0.144677 0.107 Uiso 1 1 calc GR . . . .
H71B H 0.227636 0.223878 0.161721 0.107 Uiso 1 1 calc GR . . . .
H71C H 0.290018 0.251276 0.158683 0.107 Uiso 1 1 calc GR . . . .
C72 C 0.1761(2) 0.26740(12) 0.22784(13) 0.0894(15) Uani 1 1 d . . . . .
H72A H 0.172846 0.278652 0.259138 0.134 Uiso 1 1 calc GR . . . .
H72B H 0.161838 0.236147 0.225662 0.134 Uiso 1 1 calc GR . . . .
H72C H 0.150913 0.286006 0.205781 0.134 Uiso 1 1 calc GR . . . .
C73 C 0.2826(3) 0.23706(12) 0.24992(16) 0.120(2) Uani 1 1 d . . . . .
H73A H 0.321985 0.230647 0.237776 0.180 Uiso 1 1 calc GR . . . .
H73B H 0.259914 0.208912 0.252637 0.180 Uiso 1 1 calc GR . . . .
H73C H 0.289885 0.251148 0.280338 0.180 Uiso 1 1 calc GR . . . .
C74 C 0.13676(16) 0.69465(11) 0.10674(12) 0.0535(9) Uani 1 1 d . . . . .
C75 C 0.10668(19) 0.67847(12) 0.05886(12) 0.0679(11) Uani 1 1 d . . . . .
H75A H 0.138671 0.673244 0.038042 0.102 Uiso 1 1 calc GR . . . .
H75B H 0.078357 0.701603 0.045761 0.102 Uiso 1 1 calc GR . . . .
H75C H 0.084168 0.650431 0.062787 0.102 Uiso 1 1 calc GR . . . .
C76 C 0.16522(18) 0.74222(11) 0.09909(14) 0.0688(11) Uani 1 1 d . . . . .
H76A H 0.180020 0.755237 0.128946 0.103 Uiso 1 1 calc GR . . . .
H76B H 0.133935 0.761957 0.083657 0.103 Uiso 1 1 calc GR . . . .
H76C H 0.199481 0.739195 0.079901 0.103 Uiso 1 1 calc GR . . . .
C77 C 0.08631(19) 0.70015(14) 0.14067(13) 0.0762(12) Uani 1 1 d . . . . .
H77A H 0.067185 0.670891 0.145392 0.114 Uiso 1 1 calc GR . . . .
H77B H 0.055160 0.721408 0.127737 0.114 Uiso 1 1 calc GR . . . .
H77C H 0.104835 0.711618 0.170250 0.114 Uiso 1 1 calc GR . . . .
C163 C 0.5030(7) 0.8684(3) 0.4035(5) 0.117(4) Uani 0.475(8) 1 d D U . A 2
H16A H 0.543832 0.865919 0.420024 0.176 Uiso 0.475(8) 1 calc GR . . A 2
H16B H 0.486713 0.898678 0.407746 0.176 Uiso 0.475(8) 1 calc GR . . A 2
H16C H 0.505690 0.862758 0.370643 0.176 Uiso 0.475(8) 1 calc GR . . A 2
C164 C 0.4626(6) 0.8447(4) 0.4789(3) 0.105(4) Uani 0.475(8) 1 d D U . A 2
H16G H 0.431205 0.825623 0.490858 0.158 Uiso 0.475(8) 1 calc GR . . A 2
H16H H 0.453306 0.876420 0.484540 0.158 Uiso 0.475(8) 1 calc GR . . A 2
H16I H 0.502796 0.837181 0.494392 0.158 Uiso 0.475(8) 1 calc GR . . A 2
C165 C 0.3963(6) 0.8461(5) 0.4037(5) 0.090(4) Uani 0.475(8) 1 d D U . A 2
H16D H 0.389991 0.839596 0.370666 0.134 Uiso 0.475(8) 1 calc GR . . A 2
H16E H 0.387239 0.877843 0.409109 0.134 Uiso 0.475(8) 1 calc GR . . A 2
H16F H 0.368902 0.827117 0.420277 0.134 Uiso 0.475(8) 1 calc GR . . A 2
C167 C 0.9018(4) 0.5372(3) 0.5397(3) 0.059(3) Uani 0.460(6) 1 d D . . B 2
H16P H 0.873768 0.547462 0.561935 0.088 Uiso 0.460(6) 1 calc GR . . B 2
H16Q H 0.916610 0.563153 0.523237 0.088 Uiso 0.460(6) 1 calc GR . . B 2
H16R H 0.936647 0.521571 0.556132 0.088 Uiso 0.460(6) 1 calc GR . . B 2
C168 C 0.9110(4) 0.4837(3) 0.4733(3) 0.059(2) Uani 0.460(6) 1 d D . . B 2
H16J H 0.887148 0.461117 0.454865 0.089 Uiso 0.460(6) 1 calc GR . . B 2
H16K H 0.945686 0.468963 0.490923 0.089 Uiso 0.460(6) 1 calc GR . . B 2
H16L H 0.926324 0.506434 0.452906 0.089 Uiso 0.460(6) 1 calc GR . . B 2
C169 C 0.8561(4) 0.4591(2) 0.5403(3) 0.061(3) Uani 0.460(6) 1 d D . . B 2
H16M H 0.826266 0.466702 0.562158 0.092 Uiso 0.460(6) 1 calc GR . . B 2
H16N H 0.894530 0.449450 0.557178 0.092 Uiso 0.460(6) 1 calc GR . . B 2
H16O H 0.839889 0.434730 0.520066 0.092 Uiso 0.460(6) 1 calc GR . . B 2
N83 N 0.33266(13) 0.42523(7) 0.40305(8) 0.0436(6) Uani 1 1 d . . . . .
C84 C 0.39029(15) 0.39640(9) 0.39899(10) 0.0453(8) Uani 1 1 d . . . . .
H84A H 0.423446 0.416458 0.390280 0.054 Uiso 1 1 calc R . . . .
H84B H 0.381358 0.374761 0.373408 0.054 Uiso 1 1 calc R . . . .
C85 C 0.41469(16) 0.36960(10) 0.44237(11) 0.0504(9) Uani 1 1 d . . . . .
H85A H 0.382371 0.349171 0.451803 0.060 Uiso 1 1 calc R . . . .
H85B H 0.426015 0.390626 0.468109 0.060 Uiso 1 1 calc R . . . .
C86 C 0.47201(17) 0.34159(10) 0.43147(11) 0.0544(9) Uani 1 1 d . . . . .
H86A H 0.461134 0.323010 0.403716 0.065 Uiso 1 1 calc R . . . .
H86B H 0.504995 0.362539 0.424298 0.065 Uiso 1 1 calc R . . . .
C87 C 0.49673(19) 0.31023(11) 0.47175(12) 0.0654(10) Uani 1 1 d . . . . .
H87A H 0.534062 0.295155 0.463657 0.098 Uiso 1 1 calc GR . . . .
H87B H 0.465655 0.287609 0.477226 0.098 Uiso 1 1 calc GR . . . .
H87C H 0.506027 0.328196 0.499718 0.098 Uiso 1 1 calc GR . . . .
C88 C 0.27815(16) 0.39565(10) 0.41599(10) 0.0486(8) Uani 1 1 d . . . . .
H88A H 0.291104 0.379429 0.444929 0.058 Uiso 1 1 calc R . . . .
H88B H 0.243973 0.415852 0.422364 0.058 Uiso 1 1 calc R . . . .
C89 C 0.25372(17) 0.36082(10) 0.37963(11) 0.0517(9) Uani 1 1 d . . . . .
H89A H 0.287248 0.340183 0.372867 0.062 Uiso 1 1 calc R . . . .
H89B H 0.239146 0.376513 0.350716 0.062 Uiso 1 1 calc R . . . .
C90 C 0.2006(2) 0.33337(13) 0.39714(12) 0.0725(12) Uani 1 1 d . . . . .
H90A H 0.216180 0.316245 0.424903 0.087 Uiso 1 1 calc R . . . .
H90B H 0.168758 0.354423 0.406254 0.087 Uiso 1 1 calc R . . . .
C91 C 0.17107(19) 0.30026(11) 0.36086(12) 0.0672(11) Uani 1 1 d . . . . .
H91A H 0.151650 0.317188 0.334611 0.101 Uiso 1 1 calc GR . . . .
H91B H 0.140112 0.282108 0.374610 0.101 Uiso 1 1 calc GR . . . .
H91C H 0.202715 0.280438 0.350316 0.101 Uiso 1 1 calc GR . . . .
C92 C 0.31694(16) 0.44842(9) 0.35578(10) 0.0451(8) Uani 1 1 d . . . . .
H92B H 0.314786 0.425022 0.331476 0.054 Uiso 1 1 calc R . . . .
H92A H 0.350908 0.469038 0.349979 0.054 Uiso 1 1 calc R . . . .
C93 C 0.25615(16) 0.47556(9) 0.35107(10) 0.0473(8) Uani 1 1 d . . . . .
H93A H 0.222932 0.457125 0.362325 0.057 Uiso 1 1 calc R . . . .
H93B H 0.260819 0.503055 0.370292 0.057 Uiso 1 1 calc R . . . .
C94 C 0.23892(16) 0.48881(10) 0.30062(10) 0.0491(8) Uani 1 1 d . . . . .
H94A H 0.236512 0.461176 0.281535 0.059 Uiso 1 1 calc R . . . .
H94B H 0.271954 0.507889 0.290035 0.059 Uiso 1 1 calc R . . . .
C95 C 0.17739(17) 0.51452(11) 0.29249(12) 0.0605(10) Uani 1 1 d . . . . .
H95A H 0.169304 0.521595 0.259652 0.091 Uiso 1 1 calc GR . . . .
H95B H 0.179753 0.542509 0.310368 0.091 Uiso 1 1 calc GR . . . .
H95C H 0.144199 0.495717 0.302300 0.091 Uiso 1 1 calc GR . . . .
C96 C 0.34458(16) 0.46084(9) 0.44180(10) 0.0470(8) Uani 1 1 d . . . . .
H96A H 0.306971 0.479159 0.442799 0.056 Uiso 1 1 calc R . . . .
H96B H 0.351240 0.444732 0.471580 0.056 Uiso 1 1 calc R . . . .
C97 C 0.39892(16) 0.49319(9) 0.43800(10) 0.0464(8) Uani 1 1 d . . . . .
H97A H 0.393490 0.509516 0.408286 0.056 Uiso 1 1 calc R . . . .
H97B H 0.437480 0.475721 0.438754 0.056 Uiso 1 1 calc R . . . .
C98 C 0.40310(17) 0.52753(10) 0.47841(11) 0.0517(9) Uani 1 1 d . . . . .
H98A H 0.363531 0.543595 0.478595 0.062 Uiso 1 1 calc R . . . .
H98B H 0.410455 0.511081 0.507951 0.062 Uiso 1 1 calc R . . . .
C99 C 0.45504(18) 0.56233(11) 0.47460(12) 0.0615(10) Uani 1 1 d . . . . .
H99A H 0.447309 0.579322 0.445835 0.092 Uiso 1 1 calc GR . . . .
H99B H 0.494368 0.546607 0.474748 0.092 Uiso 1 1 calc GR . . . .
H99C H 0.456311 0.583089 0.500817 0.092 Uiso 1 1 calc GR . . . .
C63 C 0.4708(5) 0.8575(3) 0.3668(4) 0.102(4) Uani 0.525(8) 1 d D U . A 1
H3AA H 0.512155 0.851182 0.358111 0.152 Uiso 0.525(8) 1 calc GR . . A 1
H3AB H 0.464028 0.890075 0.366890 0.152 Uiso 0.525(8) 1 calc GR . . A 1
H3AC H 0.440571 0.843266 0.344539 0.152 Uiso 0.525(8) 1 calc GR . . A 1
C64 C 0.5113(5) 0.8617(2) 0.4490(4) 0.097(4) Uani 0.525(8) 1 d D U . A 1
H2AD H 0.519554 0.847485 0.479273 0.145 Uiso 0.525(8) 1 calc GR . . A 1
H2AE H 0.497268 0.892696 0.452986 0.145 Uiso 0.525(8) 1 calc GR . . A 1
H2AF H 0.548868 0.862020 0.433149 0.145 Uiso 0.525(8) 1 calc GR . . A 1
C65 C 0.3955(5) 0.8419(4) 0.4267(4) 0.076(3) Uani 0.525(8) 1 d D U . A 1
H02U H 0.385532 0.827342 0.455234 0.114 Uiso 0.525(8) 1 calc GR . . A 1
H02S H 0.371482 0.828073 0.400381 0.114 Uiso 0.525(8) 1 calc GR . . A 1
H02T H 0.385821 0.874056 0.427887 0.114 Uiso 0.525(8) 1 calc GR . . A 1
C67 C 0.9213(3) 0.53859(19) 0.4830(2) 0.055(2) Uani 0.540(6) 1 d D . . B 1
H02Y H 0.921137 0.531104 0.450265 0.083 Uiso 0.540(6) 1 calc GR . . B 1
HK H 0.962143 0.532983 0.498535 0.083 Uiso 0.540(6) 1 calc GR . . B 1
HL H 0.910729 0.570423 0.486292 0.083 Uiso 0.540(6) 1 calc GR . . B 1
C68 C 0.8854(3) 0.46062(19) 0.5005(3) 0.059(2) Uani 0.540(6) 1 d D . . B 1
H1AB H 0.854185 0.441187 0.512292 0.089 Uiso 0.540(6) 1 calc GR . . B 1
H1AC H 0.925303 0.454290 0.517185 0.089 Uiso 0.540(6) 1 calc GR . . B 1
H1AD H 0.887432 0.454757 0.467590 0.089 Uiso 0.540(6) 1 calc GR . . B 1
C69 C 0.8761(4) 0.5240(3) 0.5591(3) 0.061(2) Uani 0.540(6) 1 d D . . B 1
H02V H 0.864718 0.555894 0.559846 0.091 Uiso 0.540(6) 1 calc GR . . B 1
H02W H 0.918543 0.520337 0.572272 0.091 Uiso 0.540(6) 1 calc GR . . B 1
H02X H 0.848871 0.506504 0.577231 0.091 Uiso 0.540(6) 1 calc GR . . B 1
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 0.0063 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0112 0.0059 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1018 0.0938 '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_3
O79 P78 O80 107.03(11) .
O79 P78 O81 111.04(12) .
O79 P78 O82 115.85(12) .
O81 P78 O80 102.06(12) .
O82 P78 O80 110.07(11) .
O82 P78 O81 109.86(11) .
C4 N3 C2 108.3(2) .
C7 N6 C5 107.7(2) .
C22 N23 C24 107.4(2) .
C27 N26 C25 107.4(2) .
C41 N42 C43 117.9(2) .
C47 N48 C47 111.2(3) 2_655
C2 C1 C20 117.0(3) .
C2 C1 C51 120.8(3) .
C20 C1 C51 122.0(3) .
N3 C2 C1 128.7(3) .
N3 C2 C17 109.3(3) .
C1 C2 C17 121.9(3) .
N3 C4 C5 130.1(3) .
N3 C4 C16 110.5(3) .
C5 C4 C16 119.4(3) .
C4 C5 N6 128.8(3) .
C13 C5 N6 110.3(3) .
C13 C5 C4 120.8(3) .
N6 C7 C8 129.5(3) .
N6 C7 C12 109.5(3) .
C8 C7 C12 121.0(3) .
C7 C8 C52 121.9(3) .
C9 C8 C7 116.6(3) .
C9 C8 C52 121.5(3) .
C8 C9 C10 124.4(3) .
C9 C10 C66 121.0(3) .
C11 C10 C9 116.9(3) .
C11 C10 C66 122.1(3) .
C12 C11 C10 121.3(3) .
C7 C12 C13 106.2(3) .
C11 C12 C7 119.9(3) .
C11 C12 C13 133.9(3) .
C5 C13 C12 106.2(3) .
C5 C13 C14 120.0(3) .
C14 C13 C12 133.8(3) .
C15 C14 C13 119.0(3) .
C14 C15 C16 121.2(3) .
C4 C16 C17 105.2(3) .
C15 C16 C4 119.6(3) .
C15 C16 C17 135.3(3) .
C2 C17 C16 106.7(3) .
C2 C17 C18 119.4(3) .
C18 C17 C16 133.7(3) .
C19 C18 C17 120.2(3) .
C18 C19 C20 118.4(3) .
C18 C19 C62 120.5(3) .
C20 C19 C62 121.1(3) .
C1 C20 C19 123.0(3) .
C22 C21 C40 116.3(3) .
C22 C21 C55 125.4(3) .
C40 C21 C55 118.3(3) .
N23 C22 C21 130.5(3) .
N23 C22 C37 109.4(3) .
C37 C22 C21 120.1(3) .
N23 C24 C25 131.3(3) .
N23 C24 C36 110.4(2) .
C36 C24 C25 118.2(3) .
N26 C25 C24 130.3(3) .
N26 C25 C33 110.8(2) .
C33 C25 C24 118.8(3) .
N26 C27 C28 128.9(3) .
N26 C27 C32 109.5(2) .
C32 C27 C28 121.5(3) .
C27 C28 C56 121.7(3) .
C29 C28 C27 116.1(3) .
C29 C28 C56 122.1(3) .
C30 C29 C28 124.5(3) .
C29 C30 C31 117.4(3) .
C29 C30 C74 122.6(3) .
C31 C30 C74 120.0(3) .
C30 C31 C32 120.5(3) .
C27 C32 C31 120.0(3) .
C27 C32 C33 107.2(3) .
C31 C32 C33 132.8(3) .
C25 C33 C32 105.0(3) .
C25 C33 C34 122.4(3) .
C34 C33 C32 132.6(3) .
C35 C34 C33 119.2(3) .
C34 C35 C36 119.2(3) .
C24 C36 C35 122.1(3) .
C24 C36 C37 105.5(3) .
C35 C36 C37 132.3(3) .
C22 C37 C36 107.1(3) .
C38 C37 C22 120.9(3) .
C38 C37 C36 131.9(3) .
C39 C38 C37 120.6(3) .
C38 C39 C40 117.6(3) .
C38 C39 C70 120.1(3) .
C40 C39 C70 122.3(3) .
C39 C40 C21 124.3(3) .
N42 C41 C46 122.6(3) .
N42 C41 C53 118.8(3) .
C46 C41 C53 118.5(3) .
N42 C43 C44 121.7(3) .
N42 C43 C54 118.8(3) .
C44 C43 C54 119.5(3) .
C45 C44 C43 119.4(3) .
C44 C45 C46 119.0(3) .
C45 C46 C41 119.4(3) .
N48 C47 C49 106.3(3) .
N48 C47 C57 124.1(3) .
C49 C47 C57 129.6(3) .
C47 C49 C49 108.1(2) 2_655
C51 C50 C58 177.5(3) .
C50 C51 C1 173.3(3) .
C53 C52 C8 177.5(3) .
C52 C53 C41 173.3(3) .
C55 C54 C43 172.5(3) .
C54 C55 C21 172.2(3) .
C57 C56 C28 175.1(3) .
C56 C57 C47 175.3(3) .
O59 C58 C50 110.2(3) .
O59 C58 C60 109.9(2) .
O59 C58 C61 105.2(2) .
C50 C58 C60 110.3(2) .
C50 C58 C61 109.5(2) .
C60 C58 C61 111.6(3) .
C19 C62 C164 107.0(4) .
C19 C62 C63 101.0(4) .
C163 C62 C19 115.4(6) .
C163 C62 C164 108.4(7) .
C163 C62 C165 110.2(8) .
C165 C62 C19 113.0(6) .
C165 C62 C164 101.8(7) .
C64 C62 C19 112.6(4) .
C64 C62 C63 100.9(7) .
C64 C62 C65 122.6(7) .
C65 C62 C19 112.7(5) .
C65 C62 C63 103.2(6) .
C10 C66 C168 113.1(4) .
C10 C66 C169 107.5(4) .
C10 C66 C67 104.2(3) .
C10 C66 C69 108.9(4) .
C167 C66 C10 117.4(5) .
C167 C66 C168 114.5(6) .
C167 C66 C169 103.7(5) .
C168 C66 C169 97.9(5) .
C68 C66 C10 116.3(4) .
C68 C66 C67 108.0(4) .
C68 C66 C69 115.9(5) .
C69 C66 C67 101.9(5) .
C39 C70 C72 111.0(3) .
C71 C70 C39 109.0(3) .
C71 C70 C72 107.6(3) .
C73 C70 C39 111.2(3) .
C73 C70 C71 109.8(4) .
C73 C70 C72 108.1(4) .
C30 C74 C76 112.2(3) .
C75 C74 C30 110.7(3) .
C75 C74 C76 106.9(3) .
C77 C74 C30 109.5(3) .
C77 C74 C75 109.4(3) .
C77 C74 C76 108.1(3) .
C84 N83 C88 111.0(2) .
C84 N83 C92 107.3(2) .
C84 N83 C96 110.5(2) .
C92 N83 C88 110.6(2) .
C92 N83 C96 110.7(2) .
C96 N83 C88 106.9(2) .
N83 C84 C85 116.7(2) .
C84 C85 C86 109.4(3) .
C87 C86 C85 113.4(3) .
C89 C88 N83 116.0(2) .
C88 C89 C90 110.6(3) .
C91 C90 C89 113.1(3) .
N83 C92 C93 115.4(2) .
C94 C93 C92 110.6(2) .
C93 C94 C95 114.1(3) .
C97 C96 N83 116.9(2) .
C96 C97 C98 110.4(3) .
C99 C98 C97 112.2(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P78 O79 1.486(2) .
P78 O80 1.583(2) .
P78 O81 1.5796(19) .
P78 O82 1.520(2) .
O59 C58 1.437(3) .
N3 C2 1.382(4) .
N3 C4 1.363(4) .
N6 C5 1.398(3) .
N6 C7 1.370(4) .
N23 C22 1.389(3) .
N23 C24 1.393(4) .
N26 C25 1.382(3) .
N26 C27 1.379(3) .
N42 C41 1.339(4) .
N42 C43 1.352(4) .
N48 C47 1.355(3) .
N48 C47 1.355(3) 2_655
C1 C2 1.384(4) .
C1 C20 1.396(4) .
C1 C51 1.445(4) .
C2 C17 1.395(4) .
C4 C5 1.397(4) .
C4 C16 1.403(4) .
C5 C13 1.379(4) .
C7 C8 1.400(4) .
C7 C12 1.412(4) .
C8 C9 1.392(4) .
C8 C52 1.432(4) .
C9 C10 1.401(4) .
C10 C11 1.401(4) .
C10 C66 1.510(5) .
C11 C12 1.382(4) .
C12 C13 1.455(4) .
C13 C14 1.424(4) .
C14 C15 1.375(4) .
C15 C16 1.401(4) .
C16 C17 1.457(4) .
C17 C18 1.407(4) .
C18 C19 1.381(5) .
C19 C20 1.398(4) .
C19 C62 1.540(5) .
C21 C22 1.407(4) .
C21 C40 1.409(4) .
C21 C55 1.428(5) .
C22 C37 1.401(4) .
C24 C25 1.412(4) .
C24 C36 1.398(4) .
C25 C33 1.386(4) .
C27 C28 1.405(4) .
C27 C32 1.386(4) .
C28 C29 1.394(4) .
C28 C56 1.419(4) .
C29 C30 1.388(4) .
C30 C31 1.394(4) .
C30 C74 1.533(4) .
C31 C32 1.401(4) .
C32 C33 1.457(4) .
C33 C34 1.399(4) .
C34 C35 1.373(4) .
C35 C36 1.403(4) .
C36 C37 1.455(4) .
C37 C38 1.391(4) .
C38 C39 1.386(5) .
C39 C40 1.387(5) .
C39 C70 1.534(4) .
C41 C46 1.392(4) .
C41 C53 1.438(4) .
C43 C44 1.410(4) .
C43 C54 1.431(5) .
C44 C45 1.363(5) .
C45 C46 1.375(4) .
C47 C49 1.368(4) .
C47 C57 1.420(4) .
C49 C49 1.388(7) 2_655
C50 C51 1.190(4) .
C50 C58 1.473(4) .
C52 C53 1.199(4) .
C54 C55 1.195(4) .
C56 C57 1.196(4) .
C58 C60 1.513(4) .
C58 C61 1.522(4) .
C62 C163 1.395(10) .
C62 C164 1.664(9) .
C62 C165 1.509(13) .
C62 C63 1.697(9) .
C62 C64 1.450(8) .
C62 C65 1.486(12) .
C66 C167 1.424(9) .
C66 C168 1.519(7) .
C66 C169 1.713(8) .
C66 C67 1.644(7) .
C66 C68 1.394(6) .
C66 C69 1.567(8) .
C70 C71 1.533(5) .
C70 C72 1.535(6) .
C70 C73 1.526(5) .
C74 C75 1.532(4) .
C74 C76 1.536(5) .
C74 C77 1.525(5) .
N83 C84 1.508(4) .
N83 C88 1.525(4) .
N83 C92 1.519(3) .
N83 C96 1.520(3) .
C84 C85 1.516(4) .
C85 C86 1.531(4) .
C86 C87 1.525(4) .
C88 C89 1.511(4) .
C89 C90 1.514(4) .
C90 C91 1.511(4) .
C92 C93 1.521(4) .
C93 C94 1.504(4) .
C94 C95 1.518(5) .
C96 C97 1.510(4) .
C97 C98 1.523(4) .
C98 C99 1.517(4) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168304558
