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_7157364
_publ_section_title
;
 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         '0.5(C H2 Cl2), C65 H54 N2 O16'
_chemical_formula_sum            'C65.5 H55 Cl N2 O16'
_chemical_formula_weight         1161.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-30
_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                90
_cell_angle_beta                 105.1060(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.4706(3)
_cell_length_b                   42.3400(9)
_cell_length_c                   19.1101(4)
_cell_measurement_reflns_used    9853
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      56.08
_cell_measurement_theta_min      2.96
_cell_volume                     12085.1(4)
_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      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0587
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            84603
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        58.936
_diffrn_reflns_theta_max         58.936
_diffrn_reflns_theta_min         2.087
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.150
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.6301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1011 before and 0.0647 after correction. The Ratio of minimum to maximum transmission is 0.8383. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       block
_exptl_crystal_F_000             4856
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.937
_refine_diff_density_min         -0.728
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details
;
 Flack x determined using 7446 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.275(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2551
_refine_ls_number_reflns         32548
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.1527
_refine_ls_R_factor_gt           0.1097
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2500P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3002
_refine_ls_wR_factor_ref         0.3468
_reflns_Friedel_coverage         0.852
_reflns_Friedel_fraction_full    0.876
_reflns_Friedel_fraction_max     0.876
_reflns_number_gt                21094
_reflns_number_total             32548
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00290a2.cif
_cod_data_source_block           danque-anti
_cod_depositor_comments
;
Adding full bibliography for 7157362--7157365.cif.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C262 H220 Cl4 N8 O64'
_cod_original_formula_weight         4646.25
_cod_original_formula_moiety         '2(C H2 Cl2), 4(C65 H54 N2 O16)'
_cod_original_formula_units_Z            2
_cod_database_code               7157364
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C09J-O08K
 1.42 with sigma of 0.02
 C19-C09J
 1.53 with sigma of 0.02
 O5AA-C6
 1.19 with sigma of 0.02
 C9-C20
 1.42 with sigma of 0.02
 C9-O04M
 1.42 with sigma of 0.02
 C2AA-C08U
 1.42 with sigma of 0.02
 C0BA-C083
 1.53 with sigma of 0.02
 C1BA-C0BA
 1.33 with sigma of 0.02
 C09D-C08Z
 1.53 with sigma of 0.02
 C9AA-C08Z
 1.33 with sigma of 0.02
 C3AA-C1AA
 1.53 with sigma of 0.02
 C4AA-C3AA
 1.33 with sigma of 0.02
 C080-C07V
 1.53 with sigma of 0.02
 C08S-C07V
 1.33 with sigma of 0.02
 C01H-C013 = C01V-C013 = C03G-C01V = C03G-C02K = C02K-C02F = C02F-C01H
 1.4 with sigma of 0.02
 H8A-H02K
 2.5 with sigma of 0.02
 H0BA-H04I
 2.5 with sigma of 0.02
 O4-O2AA
 2.5 with sigma of 0.04
 O4-C9
 2.5 with sigma of 0.04
 C1AA-C4AA
 2.87 with sigma of 0.04
 C1BA-C083
 2.87 with sigma of 0.04
 C9AA-C09D
 2.87 with sigma of 0.04
 C4AA-C1AA
 2.87 with sigma of 0.04
 C08S-C080
 2.87 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C09J) = Uanis(C07O)
Uanis(O034) = Uanis(O00G)
Uanis(C1) = Uanis(C06V)
Uanis(C7) = Uanis(C01D)
Uanis(O1AA) = Uanis(O014)
Uanis(O0AA) = Uanis(O00Y)
Uanis(C0AA) = Uanis(C08P)
Uanis(C3) = Uanis(C07P)
Uanis(C08Z) = Uanis(C07V)
Uanis(C084) = Uanis(C025)
Uanis(C07C) = Uanis(C03M)
Uanis(C06I) = Uanis(C03M)
Uanis(C087) = Uanis(C03M)
Uanis(C08F) = Uanis(C03M)
Uanis(C08N) = Uanis(C02M)
Uanis(C08C) = Uanis(C025)
Uanis(C07E) = Uanis(C04V)
Uanis(C06I) = Uanis(C02P)
Uanis(C08G) = Uanis(C050)
Uanis(C052) = Uanis(C01U)
Uanis(C06H) = Uanis(C01U)
Uanis(C073) = Uanis(C01U)
Uanis(C054) = Uanis(C01U)
Uanis(C06L) = Uanis(C01U)
Uanis(C06D) = Uanis(C02P)
Uanis(C04U) = Uanis(C02P)
Uanis(C05L) = Uanis(C01U)
Uanis(C07N) = Uanis(C02R)
Uanis(C06Z) = Uanis(C02R)
Uanis(O04M) = Uanis(O007)
Uanis(C9) = Uanis(C04O)
Uanis(C08I) = Uanis(C7)
Uanis(O02J) = Uanis(O1AA)
Uanis(C18) = Uanis(C3)
Uanis(C099) = Uanis(C0AA)
Uanis(O08K) = Uanis(C0AA)
Uanis(C19) = Uanis(C18)
Uanis(C03L) = Uanis(C04L)
Uanis(C08E) = Uanis(C05M)
Uanis(C08P) = Uanis(C04J)
Uanis(C08U) = Uanis(C05M)
Uanis(C2AA) = Uanis(C06K)
Uanis(C080) = Uanis(C07R)
Uanis(C09D) = Uanis(C1)
Uanis(C083) = Uanis(C04O)
Uanis(C8) = Uanis(C04O)
Uanis(O04R) = Uanis(O00H)
Uanis(C08Z) = Uanis(C09D)
Uanis(C20) = Uanis(C03X)
Uanis(O4) = Uanis(O00B)
Uanis(O2AA) = Uanis(O01C)
Uanis(C6) = Uanis(C03X)
Uanis(O1) = Uanis(O4)
Uanis(C5AA) = Uanis(C05M)
Uanis(C7AA) = Uanis(C06K)
Uanis(O5AA) = Uanis(O01C)
Uanis(C1AA) = Uanis(C09D)
Uanis(C057) = Uanis(C035)
Uanis(C080) = Uanis(C09D)
Uanis(C20) = Uanis(C04O)
Uanis(C03X) = Uanis(C042)
Uanis(C08H) = Uanis(C06K)
Uanis(C02D) = Uanis(C03X)
Uanis(C048) = Uanis(C05V)
Uanis(C4AA) = Uanis(C1BA)
Uanis(C08S) = Uanis(C1BA)
Uanis(C0BA) = Uanis(C07V)
Uanis(C3AA) = Uanis(C08Z)
Uanis(C4) = Uanis(C06K)
Uanis(C044) = Uanis(C057)
Uanis(C06A) = Uanis(C05K)
Uanis(C9AA) = Uanis(C1BA)
Uanis(C085) = Uanis(C049)
Uanis(C08L) = Uanis(C026)
Uanis(C05R) = Uanis(C059)
Uanis(C06M) = Uanis(C045)
Uanis(C08J) = Uanis(C08H)
Uanis(C6AA) = Uanis(C075)
Uanis(C09H) = Uanis(C02D)
Uanis(C07W) = Uanis(C06F)
Uanis(O020) = Uanis(O04R)
Uanis(Cl1) = Uanis(C06C) = Uanis(C072) = Uanis(C06W)
4.a Riding coordinates:
 N019(H019), N01S(H01S)
4.b Ternary CH refined with riding coordinates:
 C026(H026), C02Q(H02Q), C03D(H03D), C03N(H03N), C045(H045), C049(H049),
 C04Z(H04Z), C05W(H05W), C06M(H06M), C06Q(H06V), C06X(H06X), C07A(H07D),
 C07J(H07), C07X(H07X), C085(H085), C08L(H08L)
4.c Secondary CH2 refined with riding coordinates:
 C03J(H03A,H03B), C04J(H04C,H04D), C04O(H04A,H04B), C050(H05A,H05B), C059(H05C,
 H05D), C05K(H05E,H05F), C05M(H05G,H05I), C05U(H05O,H05P), C067(H06Q,H06R),
 C068(H06S,H06T), C06A(H06A,H06B), C06F(H06F,H06G), C06G(H06L,H06N), C06T(H06O,
 H06P), C06V(H06I,H06K), C070(H07O,H07P), C075(H07A,H07B), C076(H07Q,H07R),
 C07B(H07W,H07Y), C07I(H07E,H07F), C07K(H07T,H07U), C07Q(H8AA,HB), C07R(H0BA,
 HC), C07U(H07J,H07K), C07W(H07L,H07M), C080(H08T,H08U), C082(H08V,H08W),
 C083(H08A,H08B), C086(H08X,H08Y), C08E(H08I,H08J), C08G(H08C,H08D), C08P(H08P,
 H08Q), C08Q(H3BA,HD), C08U(H08R,H08S), C08V(H08,HE), C091(H09C,H09D),
 C099(H09E,H09F), C09D(H09A,H09B), C09J(H09G,H09H), C8(H8A,H8B), C1(H1A,H1B),
 C0AA(H0AA,H0AB), C9(H9A,H9B), C1AA(H1AA,H1AB), C5AA(H5AA,H5AB), C6AA(H6AA,H6AB)
4.d Aromatic/amide H refined with riding coordinates:
 N00P(H00P), N00S(H00S), N010(H010), C01G(H01G), N01N(H01N), C01U(H01U),
 N01W(H01W), C021(H021), C024(H024), C025(H025), N02G(H02G), C02K(H02K),
 C02N(H02N), C02R(H02R), C02X(H02X), C02Z(H02Z), C039(H039), C03A(H03C),
 C03B(H03E), C03F(H03F), C03G(H03G), C03I(H03I), C03M(H03M), C03O(H03O),
 C03Q(H03Q), C03V(H03V), C03Y(H03Y), C03Z(H03Z), C043(H043), C04C(H04H),
 C04D(H04I), C04H(H04J), C04L(H04L), C04P(H04P), C04T(H04T), C04Y(H04Y),
 C051(H051), C055(H055), C05D(H05J), C05F(H05K), C05G(H05L), C05H(H05H),
 C05I(H05M), C05N(H05N), C05Q(H05Q), C05Y(H05Y), C061(H061), C063(H063),
 C065(H065), C069(H069), C06H(H06H), C06J(H06J), C06P(H06U), C06S(H06W),
 C06Y(H06Y), C06Z(H06Z), C071(H071), C073(H073), C079(H079), C07C(H07C),
 C07F(H07S), C07M(H07V), C07N(H07N), C07Y(H2BA), C07Z(H07Z), C081(H081),
 C084(H084), C088(H088), C08F(H08F), C08N(H08N)
4.e Idealised Me refined as rotating group:
 C04Q(H04E,H04F,H04G), C06K(H06C,H06D,H06E), C07O(H3AA,H,HA), C07P(H07G,H07H,
 H07I), C08H(H08E,H08G,H08H), C08J(H08K,H08M,H08O), C18(H18A,H18B,H18C), C3(H3A,
 H3B,H3C), C2AA(H2AA,H2AB,H2AC), C19(H19A,H19B,H19C), C7AA(H7AA,H7AB,H7AC),
 C4(H4A,H4B,H4C)
4.f :
 C08S(H08Z), C9AA(H9AA), C4AA(H4AA), C1BA(H1BA)
;
_shelx_res_checksum              66742
_shelx_fab_checksum              4368
_olex2_submission_special_instructions 'No special instructions were received'