#------------------------------------------------------------------------------
#$Date: 2020-04-05 14:10:04 +0300 (Sun, 05 Apr 2020) $
#$Revision: 250356 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/73/7157363.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_7157363
loop_
_publ_author_name
'Yao, Huan'
'Wang, Xiaoping'
'Xie, Mo'
'Wang, Yu-Mei'
'Quan, Mao'
'Yang, Liu-Pan'
'Jiang, Wei'
_publ_section_title
;
 Mono-functionalized derivatives and revised configurational assignment of
 amide naphthotubes.
;
_journal_issue                   10
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1900
_journal_page_last               1909
_journal_paper_doi               10.1039/d0ob00290a
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C65 H54 N2 O16, 0.5(O2)'
_chemical_formula_sum            'C65 H54 N2 O17'
_chemical_formula_weight         1135.10
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-19 deposited with the CCDC.	2020-02-21 downloaded from the CCDC.
;
_cell_angle_alpha                96.716(3)
_cell_angle_beta                 99.839(3)
_cell_angle_gamma                94.798(3)
_cell_formula_units_Z            1
_cell_length_a                   9.7417(4)
_cell_length_b                   11.8403(5)
_cell_length_c                   11.9923(5)
_cell_measurement_reflns_used    4387
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      58.99
_cell_measurement_theta_min      3.77
_cell_volume                     1345.94(10)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9001
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        59.041
_diffrn_reflns_theta_max         59.041
_diffrn_reflns_theta_min         3.775
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.846
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.6737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0636 before and 0.0434 after correction. The Ratio of minimum to maximum transmission is 0.8964. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       plate
_exptl_crystal_F_000             594
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.748
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     459
_refine_ls_number_reflns         3832
_refine_ls_number_restraints     253
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0848
_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)+(0.1400P)²+1.9523P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2376
_refine_ls_wR_factor_ref         0.2558
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2932
_reflns_number_total             3832
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob00290a2.cif
_cod_data_source_block           danque-syn
_cod_depositor_comments
'Adding full bibliography for 7157362--7157365.cif.'
_cod_database_code               7157363
_shelx_shelxl_version_number     2014/7
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C31B-C30B = C31A-C30A = C33B-C32B = C33A-C32A
 1.53 with sigma of 0.02
 O7B-C31B = O7A-C31A = O7B-C32B = O7A-C32A
 1.42 with sigma of 0.02
 O6B-C31B = O6A-C31A
 1.2 with sigma of 0.02
 C27C-C26 = C27B-C26 = C27A-C26
 1.53 with sigma of 0.02
 O8B-C27B = O9A-C27A
 1.2 with sigma of 0.02
 O9B-C27B = O8A-C27A
 1.35 with sigma of 0.02
 O8A-C28A = O9B-C28B
 1.42 with sigma of 0.02
 C29A-C28A = C29B-C28B
 1.53 with sigma of 0.02
 O5A-C30A
 1.4 with sigma of 0.02
 C27C-C28C
 1.2 with sigma of 0.02
 C32C-C31C
 1.2 with sigma of 0.02
 C31C-C30C
 1.53 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O5A \\sim C30A \\sim C31A \\sim O6A \\sim O7A \\sim C32A \\sim C33A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02
C26 \\sim C27C \\sim C28C \\sim C27B \\sim O8B \\sim O9B \\sim C28B \\sim C29B:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
C32C \\sim C31C \\sim C30C \\sim O5C \\sim O5A \\sim C30A \\sim C31A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C30A) \\sim Ueq, Uanis(C31A) \\sim Ueq, Uanis(C32A) \\sim Ueq,
Uanis(C33A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C32C) \\sim Ueq, Uanis(C31C) \\sim Ueq, Uanis(C30C) \\sim Ueq: with sigma
of 0.005 and sigma for terminal atoms of 0.01
Uanis(O4A) = Uanis(O4B)
Uanis(O5B) = Uanis(O3)
Uanis(O6B) = Uanis(O7B)
Uanis(O7B) = Uanis(O7A)
Uanis(C32B) = Uanis(C32A)
Uanis(C33B) = Uanis(C33A)
Uanis(O6B) = Uanis(O6A)
Uanis(C30A) = Uanis(C30B)
Uanis(C32B) = Uanis(C30A)
Uanis(C31B) = Uanis(C31A)
Uanis(C28A) = Uanis(C27A)
Uanis(O9A) = Uanis(O8B)
Uanis(O8A) = Uanis(O9B)
Uanis(C27A) = Uanis(C27B)
Uanis(C28A) = Uanis(C28B)
Uanis(C29A) = Uanis(C29B)
Uanis(O5A) = Uanis(O5B)
Uanis(O5A) = Uanis(O3) = Uanis(O5C)
Uanis(O7B) = Uanis(O5A)
4. Others
 Sof(O4A)=Sof(H24A)=Sof(H24B)=1-FVAR(1)
 Sof(O4B)=Sof(H25A)=Sof(H25B)=FVAR(1)
 Fixed Sof: O9A(0.5) O8A(0.5) H26B(0.5) H26A(0.5) H26E(0.25) H26F(0.25)
 H26C(0.25) H26D(0.25) C27A(0.5) O5B(0.5) O6B(0.5) O7B(0.5) C30B(0.5) H30A(0.5)
 H30B(0.5) C31B(0.5) C32B(0.5) H32A(0.5) H32B(0.5) C33B(0.5) H33B(0.5)
 H33A(0.5) H33C(0.5) O5A(0.25) C30A(0.25) H30C(0.25) H30D(0.25) C28A(0.5)
 H28A(0.5) H28B(0.5) C29A(0.5) H29A(0.5) H29B(0.5) H29C(0.5) C31A(0.25)
 O7A(0.25) C32A(0.25) H32C(0.25) H32D(0.25) C33A(0.25) H33E(0.25) H33F(0.25)
 H33D(0.25) O6A(0.25) C27C(0.25) C28C(0.25) H28C(0.25) O8B(0.25) O9B(0.25)
 C27B(0.25) C28B(0.25) H28D(0.25) H28E(0.25) C29B(0.25) H29D(0.25) H29E(0.25)
 H29F(0.25) O5C(0.25) C32C(0.25) H32E(0.25) C31C(0.25) C30C(0.25) H30E(0.25)
 H30F(0.25) O10B(0.5)
5.a Ternary CH refined with riding coordinates:
 C1(H1A), C3(H3)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C24(H24A,H24B), C25(H25A,H25B), C26(H26B,H26A), C26(H26E,H26F),
 C26(H26C,H26D), C30B(H30A,H30B), C32B(H32A,H32B), C30A(H30C,H30D), C28A(H28A,
 H28B), C32A(H32C,H32D), C28B(H28D,H28E), C30C(H30E,H30F)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), C10(H10), C11(H11), C15(H15), C16(H16), C20(H20),
 C21(H21)
5.d Idealised Me refined as rotating group:
 C33B(H33B,H33A,H33C), C29A(H29A,H29B,H29C), C33A(H33E,H33F,H33D), C29B(H29D,
 H29E,H29F)
5.e :
 C28C(H28C), C32C(H32E)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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
O1 O 0.8955(4) 0.9077(3) 0.3664(3) 0.0716(11) Uani 1 1 d . . . . .
O2 O 0.9044(3) 0.7393(3) 0.2510(3) 0.0600(9) Uani 1 1 d . . . . .
O3 O 0.2217(3) 0.3265(2) 0.0680(2) 0.0518(6) Uani 1 1 d . . . . .
O4A O 0.5202(10) 0.0614(5) 0.2155(5) 0.0663(14) Uani 0.447(5) 1 d . . P A 2
O4B O 0.4805(8) 0.2033(5) 0.0647(4) 0.0663(14) Uani 0.553(5) 1 d . . P A 1
O9A O 0.0678(10) 0.1424(8) 0.0749(9) 0.087(3) Uani 0.5 1 d D . P B 1
O8A O -0.1194(10) 0.2287(10) 0.0135(9) 0.077(2) Uani 0.5 1 d D . P B 1
N1 N 0.5069(4) 0.2486(3) 0.2504(3) 0.0518(10) Uani 1 1 d . . . . .
H1 H 0.4995 0.3046 0.3034 0.062 Uiso 1 1 calc R . . . .
C1 C 0.8864(6) 0.8581(4) 0.2517(4) 0.0603(13) Uani 1 1 d . . . . .
H1A H 0.9662 0.8950 0.2217 0.072 Uiso 1 1 calc R . . . .
C2 C 0.7533(5) 0.8795(4) 0.1783(4) 0.0563(12) Uani 1 1 d . . . . .
H2A H 0.7534 0.8515 0.0973 0.068 Uiso 1 1 calc R . . . .
H2B H 0.7433 0.9624 0.1853 0.068 Uiso 1 1 calc R . . . .
C3 C 0.6327(5) 0.8153(3) 0.2194(3) 0.0441(10) Uani 1 1 d . . . . .
H3 H 0.5401 0.8305 0.1765 0.053 Uiso 1 1 calc R . . . .
C4 C 0.6452(5) 0.8528(3) 0.3473(3) 0.0460(11) Uani 1 1 d . . . . .
C5 C 0.7732(6) 0.8928(4) 0.4111(4) 0.0596(13) Uani 1 1 d . . . . .
C6 C 0.7957(7) 0.9208(4) 0.5308(4) 0.0768(18) Uani 1 1 d . . . . .
H6 H 0.8860 0.9512 0.5719 0.092 Uiso 1 1 calc R . . . .
C7 C 0.6876(6) 0.9041(4) 0.5871(4) 0.0632(15) Uani 1 1 d . . . . .
H7 H 0.7040 0.9193 0.6681 0.076 Uiso 1 1 calc R . . . .
C8 C 0.5512(5) 0.8644(3) 0.5272(3) 0.0462(11) Uani 1 1 d . . . . .
C9 C 0.5284(5) 0.8415(3) 0.4061(3) 0.0456(11) Uani 1 1 d . . . . .
C10 C 0.3902(5) 0.8073(4) 0.3483(4) 0.0569(13) Uani 1 1 d . . . . .
H10 H 0.3720 0.7964 0.2671 0.068 Uiso 1 1 calc R . . . .
C11 C 0.2817(6) 0.7893(5) 0.4043(4) 0.0719(16) Uani 1 1 d . . . . .
H11 H 0.1898 0.7659 0.3623 0.086 Uiso 1 1 calc R . . . .
C12 C 0.3056(5) 0.8054(5) 0.5237(4) 0.0585(13) Uani 1 1 d . . . . .
C13 C 0.4362(5) 0.8442(3) 0.5846(3) 0.0449(11) Uani 1 1 d . . . . .
C14 C 0.7872(4) 0.6604(4) 0.2239(3) 0.0449(10) Uani 1 1 d . . . . .
C15 C 0.8162(5) 0.5459(4) 0.2229(3) 0.0506(11) Uani 1 1 d . . . . .
H15 H 0.9104 0.5289 0.2409 0.061 Uiso 1 1 calc R . . . .
C16 C 0.7105(5) 0.4596(3) 0.1965(3) 0.0470(11) Uani 1 1 d . . . . .
H16 H 0.7309 0.3829 0.1997 0.056 Uiso 1 1 calc R . . . .
C17 C 0.5701(4) 0.4829(3) 0.1641(3) 0.0407(10) Uani 1 1 d . . . . .
C18 C 0.5414(4) 0.5988(3) 0.1633(3) 0.0378(9) Uani 1 1 d . . . . .
C19 C 0.6525(4) 0.6891(3) 0.2002(3) 0.0394(10) Uani 1 1 d . . . . .
C20 C 0.4022(4) 0.6186(3) 0.1204(3) 0.0410(10) Uani 1 1 d . . . . .
H20 H 0.3817 0.6949 0.1142 0.049 Uiso 1 1 calc R . . . .
C21 C 0.2959(5) 0.5316(4) 0.0876(4) 0.0462(10) Uani 1 1 d . . . . .
H21 H 0.2036 0.5482 0.0594 0.055 Uiso 1 1 calc R . . . .
C22 C 0.3231(5) 0.4188(3) 0.0955(3) 0.0441(10) Uani 1 1 d . . . . .
C23 C 0.4575(5) 0.3937(3) 0.1307(3) 0.0446(10) Uani 1 1 d . . . . .
C24 C 0.4860(5) 0.2717(3) 0.1384(4) 0.0544(12) Uani 1 1 d . . . . .
H24A H 0.4058 0.2199 0.0930 0.065 Uiso 0.447(5) 1 calc R . P A 2
H24B H 0.5702 0.2567 0.1054 0.065 Uiso 0.447(5) 1 calc R . P A 2
C25 C 0.5384(5) 0.1454(3) 0.2862(3) 0.0453(11) Uani 1 1 d . . . . .
H25A H 0.6231 0.1222 0.2582 0.054 Uiso 0.553(5) 1 calc R . P A 1
H25B H 0.4599 0.0857 0.2538 0.054 Uiso 0.553(5) 1 calc R . P A 1
C26 C 0.0810(5) 0.3483(4) 0.0381(5) 0.0669(13) Uani 1 1 d D U . . .
H26B H 0.0596 0.3709 -0.0394 0.080 Uiso 0.5 1 calc R . P C 1
H26A H 0.0540 0.4065 0.0943 0.080 Uiso 0.5 1 calc R . P C 1
H26E H 0.0767 0.3994 -0.0219 0.080 Uiso 0.25 1 calc R . P D 3
H26F H 0.0557 0.3921 0.1058 0.080 Uiso 0.25 1 calc R . P D 3
H26C H 0.0729 0.3894 -0.0297 0.080 Uiso 0.25 1 calc R . P E 2
H26D H 0.0584 0.4007 0.1015 0.080 Uiso 0.25 1 calc R . P E 2
C27A C 0.0147(12) 0.2274(11) 0.0437(14) 0.0750(18) Uani 0.5 1 d D . P B 1
O5B O 0.1973(12) 0.7643(8) 0.5855(10) 0.0518(6) Uani 0.5 1 d . . P F 1
O6B O 0.0197(9) 0.6886(6) 0.7146(7) 0.0518(6) Uani 0.5 1 d D . P F 1
O7B O -0.1314(6) 0.6101(6) 0.5659(5) 0.0518(6) Uani 0.5 1 d D . P F 1
C30B C 0.0738(12) 0.6956(8) 0.5289(9) 0.0502(14) Uani 0.5 1 d D . P F 1
H30A H 0.0973 0.6216 0.4935 0.060 Uiso 0.5 1 calc R . P F 1
H30B H 0.0235 0.7345 0.4680 0.060 Uiso 0.5 1 calc R . P F 1
C31B C -0.0153(15) 0.676(2) 0.6147(10) 0.0559(16) Uani 0.5 1 d D . P F 1
C32B C -0.2248(9) 0.5832(9) 0.6412(7) 0.0502(14) Uani 0.5 1 d D . P F 1
H32A H -0.1882 0.5255 0.6887 0.060 Uiso 0.5 1 calc R . P F 1
H32B H -0.2352 0.6526 0.6924 0.060 Uiso 0.5 1 calc R . P F 1
C33B C -0.3564(10) 0.5392(8) 0.5712(9) 0.060(2) Uani 0.5 1 d D . P F 1
H33B H -0.3450 0.4693 0.5227 0.090 Uiso 0.5 1 calc GR . P F 1
H33A H -0.3899 0.5963 0.5231 0.090 Uiso 0.5 1 calc GR . P F 1
H33C H -0.4245 0.5217 0.6198 0.090 Uiso 0.5 1 calc GR . P F 1
O5A O 0.205(3) 0.7889(14) 0.586(2) 0.0518(6) Uani 0.25 1 d D U P F 2
C30A C 0.074(2) 0.7365(18) 0.527(2) 0.0502(14) Uani 0.25 1 d D U P F 2
H30C H 0.0852 0.6763 0.4654 0.060 Uiso 0.25 1 calc R . P F 2
H30D H 0.0176 0.7936 0.4919 0.060 Uiso 0.25 1 calc R . P F 2
C28A C -0.2120(11) 0.1286(9) 0.0147(10) 0.0750(18) Uani 0.5 1 d D . P B 1
H28A H -0.3056 0.1510 0.0238 0.090 Uiso 0.5 1 calc R . P B 1
H28B H -0.1758 0.0895 0.0806 0.090 Uiso 0.5 1 calc R . P B 1
C29A C -0.2246(15) 0.0507(13) -0.0908(11) 0.102(4) Uani 0.5 1 d D . P B 1
H29A H -0.2428 0.0932 -0.1562 0.152 Uiso 0.5 1 calc GR . P B 1
H29B H -0.3021 -0.0090 -0.0956 0.152 Uiso 0.5 1 calc GR . P B 1
H29C H -0.1372 0.0154 -0.0916 0.152 Uiso 0.5 1 calc GR . P B 1
C31A C 0.001(3) 0.684(4) 0.6157(18) 0.0559(16) Uani 0.25 1 d D U P F 2
O7A O -0.1350(12) 0.6697(11) 0.5475(10) 0.0518(6) Uani 0.25 1 d D U P F 2
C32A C -0.2453(19) 0.6280(14) 0.6034(16) 0.0502(14) Uani 0.25 1 d D U P F 2
H32C H -0.2238 0.6646 0.6839 0.060 Uiso 0.25 1 calc R . P F 2
H32D H -0.3332 0.6556 0.5674 0.060 Uiso 0.25 1 calc R . P F 2
C33A C -0.273(2) 0.5072(15) 0.6041(19) 0.060(2) Uani 0.25 1 d D U P F 2
H33E H -0.2762 0.4672 0.5272 0.090 Uiso 0.25 1 calc GR . P F 2
H33F H -0.3627 0.4908 0.6281 0.090 Uiso 0.25 1 calc GR . P F 2
H33D H -0.1979 0.4811 0.6574 0.090 Uiso 0.25 1 calc GR . P F 2
O6A O 0.0442(18) 0.7197(12) 0.7177(14) 0.0518(6) Uani 0.25 1 d D U P F 2
C27C C -0.031(3) 0.250(2) -0.004(4) 0.074(3) Uani 0.25 1 d D U P B 3
C28C C -0.116(3) 0.166(2) -0.023(2) 0.078(5) Uani 0.25 1 d D U P B 3
H28C H -0.1820 0.0996 -0.0382 0.094 Uiso 0.25 1 calc R . P B 3
O8B O -0.148(2) 0.250(2) -0.021(2) 0.087(3) Uani 0.25 1 d D U P B 2
O9B O 0.0277(19) 0.1491(17) 0.0229(16) 0.077(2) Uani 0.25 1 d D U P B 2
C27B C -0.027(2) 0.2474(18) 0.012(4) 0.0750(18) Uani 0.25 1 d D U P B 2
C28B C -0.078(2) 0.0566(19) 0.0265(17) 0.0750(18) Uani 0.25 1 d D U P B 2
H28D H -0.1570 0.0874 0.0571 0.090 Uiso 0.25 1 calc R . P B 2
H28E H -0.0373 0.0029 0.0774 0.090 Uiso 0.25 1 calc R . P B 2
C29B C -0.129(3) -0.007(3) -0.094(2) 0.102(4) Uani 0.25 1 d D U P B 2
H29D H -0.0494 -0.0149 -0.1335 0.152 Uiso 0.25 1 calc GR . P B 2
H29E H -0.1962 0.0373 -0.1370 0.152 Uiso 0.25 1 calc GR . P B 2
H29F H -0.1752 -0.0824 -0.0901 0.152 Uiso 0.25 1 calc GR . P B 2
O5C O 0.2227(17) 0.8244(13) 0.5970(14) 0.0518(6) Uani 0.25 1 d . U P F 3
C32C C -0.041(3) 0.757(3) 0.719(2) 0.103(6) Uani 0.25 1 d D U P F 3
H32E H -0.0780 0.7648 0.7872 0.124 Uiso 0.25 1 calc R . P F 3
C31C C 0.008(2) 0.747(2) 0.6312(18) 0.065(3) Uani 0.25 1 d D U P F 3
C30C C 0.087(2) 0.7836(18) 0.5409(17) 0.054(3) Uani 0.25 1 d D U P F 3
H30E H 0.0896 0.7176 0.4826 0.065 Uiso 0.25 1 calc R . P F 3
H30F H 0.0422 0.8442 0.5027 0.065 Uiso 0.25 1 calc R . P F 3
O10B O -0.4297(16) 0.0331(8) -0.0174(10) 0.147(5) Uani 0.5 1 d . . P G 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C5 O1 C1 115.6(4) . . ?
C14 O2 C1 118.7(4) . . ?
C22 O3 C26 118.0(3) . . ?
C27A O8A C28A 119.9(10) . . ?
C24 N1 H1 117.1 . . ?
C25 N1 H1 117.1 . . ?
C25 N1 C24 125.8(3) . . ?
O1 C1 O2 108.2(4) . . ?
O1 C1 H1A 107.8 . . ?
O1 C1 C2 111.5(4) . . ?
O2 C1 H1A 107.8 . . ?
O2 C1 C2 113.5(4) . . ?
C2 C1 H1A 107.8 . . ?
C1 C2 H2A 110.3 . . ?
C1 C2 H2B 110.3 . . ?
C1 C2 C3 107.3(4) . . ?
H2A C2 H2B 108.5 . . ?
C3 C2 H2A 110.3 . . ?
C3 C2 H2B 110.3 . . ?
C2 C3 H3 110.9 . . ?
C4 C3 C2 108.4(4) . . ?
C4 C3 H3 110.9 . . ?
C19 C3 C2 106.6(3) . . ?
C19 C3 H3 110.9 . . ?
C19 C3 C4 108.9(3) . . ?
C5 C4 C3 119.3(4) . . ?
C5 C4 C9 117.7(4) . . ?
C9 C4 C3 122.9(4) . . ?
O1 C5 C6 113.0(5) . . ?
C4 C5 O1 124.2(4) . . ?
C4 C5 C6 122.9(5) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.6(5) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7 119.5 . . ?
C6 C7 C8 121.1(4) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 C9 118.8(4) . . ?
C7 C8 C13 122.1(4) . . ?
C9 C8 C13 119.0(4) . . ?
C8 C9 C4 119.8(4) . . ?
C10 C9 C4 122.6(4) . . ?
C10 C9 C8 117.6(4) . . ?
C9 C10 H10 118.8 . . ?
C11 C10 C9 122.5(4) . . ?
C11 C10 H10 118.8 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.9(5) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 O5B 120.4(6) . . ?
C13 C12 C11 120.4(4) . . ?
C13 C12 O5B 118.5(6) . . ?
O5A C12 C11 123.9(11) . . ?
O5A C12 C13 115.7(11) . . ?
O5C C12 C11 132.3(9) . . ?
O5C C12 C13 104.0(8) . . ?
C8 C13 C25 119.8(4) . 2_666 ?
C12 C13 C8 120.5(4) . . ?
C12 C13 C25 119.5(4) . 2_666 ?
O2 C14 C15 114.4(4) . . ?
C19 C14 O2 123.9(4) . . ?
C19 C14 C15 121.8(4) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.5(4) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.6(4) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C18 118.7(4) . . ?
C16 C17 C23 121.9(4) . . ?
C18 C17 C23 119.4(4) . . ?
C17 C18 C19 119.9(4) . . ?
C20 C18 C17 117.3(4) . . ?
C20 C18 C19 122.7(3) . . ?
C14 C19 C3 117.0(4) . . ?
C14 C19 C18 118.1(4) . . ?
C18 C19 C3 124.8(4) . . ?
C18 C20 H20 118.9 . . ?
C21 C20 C18 122.3(4) . . ?
C21 C20 H20 118.9 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.0(4) . . ?
C22 C21 H21 120.0 . . ?
O3 C22 C21 123.9(4) . . ?
C23 C22 O3 115.8(4) . . ?
C23 C22 C21 120.3(4) . . ?
C17 C23 C24 119.5(4) . . ?
C22 C23 C17 120.5(4) . . ?
C22 C23 C24 119.9(4) . . ?
O4B C24 N1 122.0(4) . . ?
O4B C24 C23 126.0(4) . . ?
N1 C24 C23 111.7(3) . . ?
N1 C24 H24A 109.3 . . ?
N1 C24 H24B 109.3 . . ?
C23 C24 H24A 109.3 . . ?
C23 C24 H24B 109.3 . . ?
H24A C24 H24B 108.0 . . ?
O4A C25 N1 118.2(4) . . ?
O4A C25 C13 130.2(4) . 2_666 ?
N1 C25 C13 110.4(3) . 2_666 ?
N1 C25 H25A 109.6 . . ?
N1 C25 H25B 109.6 . . ?
C13 C25 H25A 109.6 2_666 . ?
C13 C25 H25B 109.6 2_666 . ?
H25A C25 H25B 108.1 . . ?
O3 C26 H26B 112.4 . . ?
O3 C26 H26A 112.4 . . ?
O3 C26 H26E 107.4 . . ?
O3 C26 H26F 107.4 . . ?
O3 C26 H26C 108.1 . . ?
O3 C26 H26D 108.1 . . ?
O3 C26 C27A 96.8(6) . . ?
O3 C26 C27C 119.6(14) . . ?
O3 C26 C27B 116.9(10) . . ?
H26B C26 H26A 110.0 . . ?
H26E C26 H26F 107.0 . . ?
H26C C26 H26D 107.3 . . ?
C27A C26 H26B 112.4 . . ?
C27A C26 H26A 112.4 . . ?
C27C C26 H26E 107.4 . . ?
C27C C26 H26F 107.4 . . ?
C27B C26 H26C 108.1 . . ?
C27B C26 H26D 108.1 . . ?
O9A C27A O8A 122.7(11) . . ?
O9A C27A C26 131.0(10) . . ?
O8A C27A C26 106.2(9) . . ?
C30B O5B C12 122.0(9) . . ?
C31B O7B C32B 115.2(8) . . ?
O5B C30B H30A 110.1 . . ?
O5B C30B H30B 110.1 . . ?
O5B C30B C31B 107.8(10) . . ?
H30A C30B H30B 108.5 . . ?
C31B C30B H30A 110.1 . . ?
C31B C30B H30B 110.1 . . ?
O6B C31B O7B 120.0(12) . . ?
O6B C31B C30B 127.2(11) . . ?
O7B C31B C30B 110.0(10) . . ?
O7B C32B H32A 110.4 . . ?
O7B C32B H32B 110.4 . . ?
H32A C32B H32B 108.6 . . ?
C33B C32B O7B 106.8(7) . . ?
C33B C32B H32A 110.4 . . ?
C33B C32B H32B 110.4 . . ?
C32B C33B H33B 109.5 . . ?
C32B C33B H33A 109.5 . . ?
C32B C33B H33C 109.5 . . ?
H33B C33B H33A 109.5 . . ?
H33B C33B H33C 109.5 . . ?
H33A C33B H33C 109.5 . . ?
C12 O5A C30A 117(2) . . ?
O5A C30A H30C 110.4 . . ?
O5A C30A H30D 110.4 . . ?
O5A C30A C31A 106(2) . . ?
H30C C30A H30D 108.6 . . ?
C31A C30A H30C 110.4 . . ?
C31A C30A H30D 110.4 . . ?
O8A C28A H28A 109.5 . . ?
O8A C28A H28B 109.5 . . ?
O8A C28A C29A 110.6(10) . . ?
H28A C28A H28B 108.1 . . ?
C29A C28A H28A 109.5 . . ?
C29A C28A H28B 109.5 . . ?
C28A C29A H29A 109.5 . . ?
C28A C29A H29B 109.5 . . ?
C28A C29A H29C 109.5 . . ?
H29A C29A H29B 109.5 . . ?
H29A C29A H29C 109.5 . . ?
H29B C29A H29C 109.5 . . ?
O7A C31A C30A 95.1(17) . . ?
O6A C31A C30A 118(2) . . ?
O6A C31A O7A 132(3) . . ?
C31A O7A C32A 114.6(16) . . ?
O7A C32A H32C 107.6 . . ?
O7A C32A H32D 107.6 . . ?
H32C C32A H32D 107.0 . . ?
C33A C32A O7A 119.0(14) . . ?
C33A C32A H32C 107.6 . . ?
C33A C32A H32D 107.6 . . ?
C32A C33A H33E 109.5 . . ?
C32A C33A H33F 109.5 . . ?
C32A C33A H33D 109.5 . . ?
H33E C33A H33F 109.5 . . ?
H33E C33A H33D 109.5 . . ?
H33F C33A H33D 109.5 . . ?
C28C C27C C26 171(4) . . ?
C27C C28C H28C 180.0 . . ?
C27B O9B C28B 112.1(18) . . ?
O8B C27B C26 126(2) . . ?
O8B C27B O9B 121(2) . . ?
O9B C27B C26 112.9(16) . . ?
O9B C28B H28D 109.8 . . ?
O9B C28B H28E 109.8 . . ?
O9B C28B C29B 109.2(19) . . ?
H28D C28B H28E 108.3 . . ?
C29B C28B H28D 109.8 . . ?
C29B C28B H28E 109.8 . . ?
C28B C29B H29D 109.5 . . ?
C28B C29B H29E 109.5 . . ?
C28B C29B H29F 109.5 . . ?
H29D C29B H29E 109.5 . . ?
H29D C29B H29F 109.5 . . ?
H29E C29B H29F 109.5 . . ?
C12 O5C C30C 106.9(14) . . ?
C31C C32C H32E 180.0 . . ?
C32C C31C C30C 157(3) . . ?
O5C C30C C31C 106.7(17) . . ?
O5C C30C H30E 110.4 . . ?
O5C C30C H30F 110.4 . . ?
C31C C30C H30E 110.4 . . ?
C31C C30C H30F 110.4 . . ?
H30E C30C H30F 108.6 . . ?
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 C1 1.417(5) . ?
O1 C5 1.393(6) . ?
O2 C1 1.431(6) . ?
O2 C14 1.381(5) . ?
O3 C22 1.380(5) . ?
O3 C26 1.409(6) . ?
O4A C25 1.209(7) . ?
O4B C24 1.118(6) . ?
O9A C27A 1.236(13) . ?
O8A C27A 1.296(13) . ?
O8A C28A 1.432(12) . ?
N1 H1 0.8800 . ?
N1 C24 1.385(5) . ?
N1 C25 1.383(5) . ?
C1 H1A 1.0000 . ?
C1 C2 1.496(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.528(6) . ?
C3 H3 1.0000 . ?
C3 C4 1.527(6) . ?
C3 C19 1.519(5) . ?
C4 C5 1.362(7) . ?
C4 C9 1.442(6) . ?
C5 C6 1.410(7) . ?
C6 H6 0.9500 . ?
C6 C7 1.358(7) . ?
C7 H7 0.9500 . ?
C7 C8 1.412(7) . ?
C8 C9 1.422(6) . ?
C8 C13 1.429(6) . ?
C9 C10 1.407(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.361(7) . ?
C11 H11 0.9500 . ?
C11 C12 1.398(6) . ?
C12 C13 1.367(7) . ?
C12 O5B 1.471(12) . ?
C12 O5A 1.34(3) . ?
C12 O5C 1.305(18) . ?
C13 C25 1.515(5) 2_666 ?
C14 C15 1.407(6) . ?
C14 C19 1.374(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.357(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.416(6) . ?
C17 C18 1.424(5) . ?
C17 C23 1.426(6) . ?
C18 C19 1.429(6) . ?
C18 C20 1.415(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.369(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.394(6) . ?
C22 C23 1.374(6) . ?
C23 C24 1.504(6) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C13 1.515(5) 2_666 ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26B 0.9900 . ?
C26 H26A 0.9900 . ?
C26 H26E 0.9900 . ?
C26 H26F 0.9900 . ?
C26 H26C 0.9900 . ?
C26 H26D 0.9900 . ?
C26 C27A 1.535(12) . ?
C26 C27C 1.508(16) . ?
C26 C27B 1.491(17) . ?
O5B C30B 1.414(13) . ?
O6B C31B 1.177(11) . ?
O7B C31B 1.324(13) . ?
O7B C32B 1.430(10) . ?
C30B H30A 0.9900 . ?
C30B H30B 0.9900 . ?
C30B C31B 1.480(13) . ?
C32B H32A 0.9900 . ?
C32B H32B 0.9900 . ?
C32B C33B 1.428(12) . ?
C33B H33B 0.9800 . ?
C33B H33A 0.9800 . ?
C33B H33C 0.9800 . ?
O5A C30A 1.409(19) . ?
C30A H30C 0.9900 . ?
C30A H30D 0.9900 . ?
C30A C31A 1.541(19) . ?
C28A H28A 0.9900 . ?
C28A H28B 0.9900 . ?
C28A C29A 1.458(14) . ?
C29A H29A 0.9800 . ?
C29A H29B 0.9800 . ?
C29A H29C 0.9800 . ?
C31A O7A 1.416(19) . ?
C31A O6A 1.235(18) . ?
O7A C32A 1.443(15) . ?
C32A H32C 0.9900 . ?
C32A H32D 0.9900 . ?
C32A C33A 1.434(17) . ?
C33A H33E 0.9800 . ?
C33A H33F 0.9800 . ?
C33A H33D 0.9800 . ?
C27C C28C 1.211(18) . ?
C28C H28C 0.9500 . ?
O8B C27B 1.179(19) . ?
O9B C27B 1.330(19) . ?
O9B C28B 1.446(17) . ?
C28B H28D 0.9900 . ?
C28B H28E 0.9900 . ?
C28B C29B 1.533(18) . ?
C29B H29D 0.9800 . ?
C29B H29E 0.9800 . ?
C29B H29F 0.9800 . ?
O5C C30C 1.39(3) . ?
C32C H32E 0.9500 . ?
C32C C31C 1.220(18) . ?
C31C C30C 1.517(17) . ?
C30C H30E 0.9900 . ?
C30C H30F 0.9900 . ?
O10B O10B 1.66(3) 2_455 ?
