Mono-functionalized derivatives and revised configurational assignment of amide naphthotubes.
Yao, Huan; Wang, Xiaoping; Xie, Mo; Wang, Yu-Mei; Quan, Mao; Yang, Liu-Pan; Jiang, Wei; Organic & biomolecular chemistry 18 (2020) 1900–1909; doi:10.1039/d0ob00290a

data_7157363
_publ_section_title
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 Mono-functionalized derivatives and revised configurational assignment of
 amide naphthotubes.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; 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)
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_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       '\w and \f 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 \l/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/[\s^2^(Fo^2^)+(0.1400P)^2^+1.9523P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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
_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)
;
_shelx_res_checksum              22663
_olex2_submission_special_instructions 'No special instructions were received'