Recognition of naphthoflavones by calix[4]pyrrole[2]phenanthrene
Zeng, Fei; Tang, Lin-Li; Ding, Man-Hua; New Journal of Chemistry 47 (2023) 14118–14122; doi:10.1039/D3NJ02483K

data_7062570
_publ_section_title
;
 Recognition of naphthoflavones by calix[4]pyrrole[2]phenanthrene
;
_journal_issue                   30
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14118
_journal_page_last               14122
_journal_paper_doi               10.1039/D3NJ02483K
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         '3(C19 H12 O2), C54 H48 N4 O4, H2 O'
_chemical_formula_sum            'C111 H86 N4 O11'
_chemical_formula_weight         1651.83
_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   mixed
_audit_creation_date             2022-11-18
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_audit_update_record
;
2023-04-23 deposited with the CCDC.	2023-07-06 downloaded from the CCDC.
;
_cell_angle_alpha                102.339(3)
_cell_angle_beta                 102.319(3)
_cell_angle_gamma                109.884(3)
_cell_formula_units_Z            2
_cell_length_a                   16.299(4)
_cell_length_b                   16.315(4)
_cell_length_c                   18.435(5)
_cell_measurement_reflns_used    6825
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.06
_cell_measurement_theta_min      2.34
_cell_volume                     4279.6(19)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_unetI/netI     0.1016
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            37717
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.190
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       block
_exptl_crystal_F_000             1736
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1276
_refine_ls_number_reflns         14912
_refine_ls_number_restraints     1184
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1978
_refine_ls_R_factor_gt           0.0916
_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^)+(0.1586P)^2^+0.2228P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2419
_refine_ls_wR_factor_ref         0.3106
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6027
_reflns_number_total             14912
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj02483k2.cif
_cod_data_source_block           2210214_0m
_cod_depositor_comments
'Adding full bibliography for 7062569--7062570.cif.'
_cod_database_code               7062570
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 C45-C19 \\sim C45-C21 \\sim C21-C12 \\sim C12-C11 \\sim C13-C11 \\sim C19-C13
 with sigma of 0.02
 C033-C17 \\sim C0-C17A
 with sigma of 0.02
 C033-C6 \\sim C0-C6A
 with sigma of 0.02
 C17-C15 \\sim C17A-C15A
 with sigma of 0.02
 C15-C03A \\sim C15A-C03B
 with sigma of 0.02
 C03A-C7 \\sim C03B-C7A
 with sigma of 0.02
 C7-C6 \\sim C7A-C6A
 with sigma of 0.02
 C6-C5 \\sim C6A-C5A
 with sigma of 0.02
 C1-C9 \\sim C1A-C9A
 with sigma of 0.02
 C1-C11 \\sim C1A-C11A
 with sigma of 0.02
 C1-C2 \\sim C1A-C2A
 with sigma of 0.02
 C9-C4 \\sim C9A-C4A
 with sigma of 0.02
 C9-O10 \\sim C9A-O10A
 with sigma of 0.02
 C4-C0AA \\sim C4A-C0AB
 with sigma of 0.02
 C0AA-C12 \\sim C0AB-C12A
 with sigma of 0.02
 C12-C11 \\sim C12A-C11A
 with sigma of 0.02
 C12-C21 \\sim C12A-C21A
 with sigma of 0.02
 C11-C13 \\sim C11A-C13A
 with sigma of 0.02
 C2-C3 \\sim C2A-C3A
 with sigma of 0.02
 C2-O15 \\sim C2A-O15A
 with sigma of 0.02
 C3-C5 \\sim C3A-C5A
 with sigma of 0.02
 C5-O10 \\sim C5A-O10A
 with sigma of 0.02
 C13-C19 \\sim C13A-C19A
 with sigma of 0.02
 C19-C45 \\sim C19A-C45A
 with sigma of 0.02
 C45-C21 \\sim C45A-C21A
 with sigma of 0.02
 C033-C15 \\sim C0-C15A
 with sigma of 0.02
 C033-C7 \\sim C0-C7A
 with sigma of 0.02
 C033-C5 \\sim C0-C5A
 with sigma of 0.04
 C17-C03A \\sim C17A-C03B
 with sigma of 0.04
 C17-C6 \\sim C17A-C6A
 with sigma of 0.04
 C15-C7 \\sim C15A-C7A
 with sigma of 0.04
 C03A-C6 \\sim C03B-C6A
 with sigma of 0.04
 C7-C5 \\sim C7A-C5A
 with sigma of 0.04
 C6-C3 \\sim C6A-C3A
 with sigma of 0.04
 C6-O10 \\sim C6A-O10A
 with sigma of 0.04
 C1-C4 \\sim C1A-C4A
 with sigma of 0.04
 C1-C12 \\sim C1A-C12A
 with sigma of 0.04
 C1-C3 \\sim C1A-C3A
 with sigma of 0.04
 C1-O10 \\sim C1A-O10A
 with sigma of 0.04
 C1-C13 \\sim C1A-C13A
 with sigma of 0.04
 C1-O15 \\sim C1A-O15A
 with sigma of 0.04
 C9-C0AA \\sim C9A-C0AB
 with sigma of 0.04
 C9-C11 \\sim C9A-C11A
 with sigma of 0.04
 C9-C2 \\sim C9A-C2A
 with sigma of 0.04
 C9-C5 \\sim C9A-C5A
 with sigma of 0.04
 C4-C12 \\sim C4A-C12A
 with sigma of 0.04
 C4-O10 \\sim C4A-O10A
 with sigma of 0.04
 C0AA-C11 \\sim C0AB-C11A
 with sigma of 0.04
 C0AA-C21 \\sim C0AB-C21A
 with sigma of 0.04
 C12-C13 \\sim C12A-C13A
 with sigma of 0.04
 C12-C45 \\sim C12A-C45A
 with sigma of 0.04
 C11-C2 \\sim C11A-C2A
 with sigma of 0.04
 C11-C19 \\sim C11A-C19A
 with sigma of 0.04
 C11-C21 \\sim C11A-C21A
 with sigma of 0.04
 C2-C5 \\sim C2A-C5A
 with sigma of 0.04
 C3-O10 \\sim C3A-O10A
 with sigma of 0.04
 C3-O15 \\sim C3A-O15A
 with sigma of 0.04
 C13-C45 \\sim C13A-C45A
 with sigma of 0.04
 C19-C21 \\sim C19A-C21A
 with sigma of 0.04
 C12-C0AA \\sim C4-C0AA \\sim C9-C4 \\sim C11-C1 \\sim C12-C11 \\sim C9-C1
 with sigma of 0.02
 C9A-C4A \\sim C4A-C0AB \\sim C12A-C0AB \\sim C12A-C11A \\sim C1A-C11A \\sim
C9A-C1A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C17A \\sim C9A \\sim C4A \\sim C0AB \\sim O10A \\sim C1A \\sim C12A \\sim C5A
\\sim C2A \\sim C11A \\sim C21A \\sim C6A \\sim C3A \\sim O15A \\sim C13A \\sim
C45A \\sim C0 \\sim C7A \\sim C19A \\sim C03B \\sim C15A \\sim C19 \\sim C033
\\sim C17 \\sim C6 \\sim C15 \\sim C7 \\sim C5 \\sim C03A \\sim C3 \\sim O10
\\sim C2 \\sim C9 \\sim C1 \\sim O15 \\sim C4 \\sim C11 \\sim C0AA \\sim C12
\\sim C13 \\sim C21 \\sim C45: within 1.5A with sigma of 0.012 and sigma for
terminal atoms of 0.024
Uanis(C17A) \\sim Ueq, Uanis(C12A) \\sim Ueq, Uanis(C11A) \\sim Ueq,
Uanis(C0AB) \\sim Ueq, Uanis(C21A) \\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(C13A)
\\sim Ueq, Uanis(C4A) \\sim Ueq, Uanis(C45A) \\sim Ueq, Uanis(C2A) \\sim Ueq,
Uanis(C9A) \\sim Ueq, Uanis(C19A) \\sim Ueq, Uanis(C3A) \\sim Ueq, Uanis(O15A)
\\sim Ueq, Uanis(O10A) \\sim Ueq, Uanis(C5A) \\sim Ueq, Uanis(C6A) \\sim Ueq,
Uanis(C7A) \\sim Ueq, Uanis(C03B) \\sim Ueq, Uanis(C15A) \\sim Ueq, Uanis(C0)
\\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C6) \\sim Ueq,
Uanis(C03A) \\sim Ueq, Uanis(C033) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(O10) \\sim Ueq,
Uanis(C2) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(O15) \\sim
Ueq, Uanis(C4) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C0AA) \\sim Ueq,
Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C45)
\\sim Ueq: with sigma of 0.03 and sigma for terminal atoms of 0.06
4. Others
 Sof(C12A)=Sof(C11A)=Sof(C13A)=Sof(H13A)=Sof(C19A)=Sof(H19A)=Sof(C45A)=
 Sof(H45A)=Sof(C21A)=Sof(H21A)=Sof(C15A)=Sof(H15A)=Sof(C17A)=Sof(H17A)=Sof(C0)=
 Sof(H0)=Sof(C6A)=Sof(C7A)=Sof(H7A)=Sof(C03B)=Sof(H03H)=Sof(C5A)=Sof(C3A)=
 Sof(H3A)=Sof(C2A)=Sof(C1A)=Sof(C9A)=Sof(O10A)=Sof(O15A)=Sof(C4A)=Sof(H4A)=
 Sof(C0AB)=Sof(H0AC)=1-FVAR(1)
 Sof(C7)=Sof(H7)=Sof(C6)=Sof(C033)=Sof(H033)=Sof(C17)=Sof(H17)=Sof(C15)=
 Sof(H15)=Sof(C03A)=Sof(H03G)=Sof(C1)=Sof(C2)=Sof(C3)=Sof(H3)=Sof(C5)=Sof(O10)=
 Sof(C9)=Sof(C4)=Sof(H4)=Sof(C0AA)=Sof(H0AB)=Sof(C12)=Sof(C11)=Sof(C13)=
 Sof(H13)=Sof(C19)=Sof(H19)=Sof(C45)=Sof(H45)=Sof(C21)=Sof(H21)=Sof(O15)=FVAR(1)
5.a Free rotating group:
 O00C(H00A,H00C)
5.b Aromatic/amide H refined with riding coordinates:
 N004(H004), N006(H006), N007(H007), N00B(H00B), C00F(H00F), C00G(H00G),
 C00L(H00L), C00W(H00W), C00Z(H00Z), C017(H017), C019(H019), C01E(H01E),
 C01F(H01F), C01H(H01K), C01I(H01I), C01J(H01J), C01N(H01N), C01Q(H01Q),
 C01R(H01R), C01S(H01S), C01T(H01T), C01U(H01U), C021(H021), C022(H022),
 C023(H023), C024(H024), C025(H025), C026(H026), C02A(H02V), C02C(H02W),
 C02D(H02O), C02E(H02P), C02F(H02Z), C02H(H02Q), C02I(H02), C02J(H02R),
 C02K(H02K), C02L(H02S), C02M(H0AA), C02N(H02N), C02O(H02T), C02Q(H1AA),
 C02R(H2AA), C02S(H3AA), C02U(H02U), C02W(H4AA), C02X(H02X), C02Y(H02Y), C7(H7),
  C033(H033), C17(H17), C15(H15), C03A(H03G), C3(H3), C4(H4), C0AA(H0AB),
 C13(H13), C19(H19), C45(H45), C21(H21), C13A(H13A), C19A(H19A), C45A(H45A),
 C21A(H21A), C15A(H15A), C17A(H17A), C0(H0), C7A(H7A), C03B(H03H), C3A(H3A),
 C4A(H4A), C0AB(H0AC)
5.c Fitted hexagon refined as free rotating group:
 C7(C6,C033,C17,C15,C03A), C1(C2,C3,C5,O10,C9), C12A(C11A,C13A,C19A,C45A,C21A),
  C15A(C17A,C0,C6A,C7A,C03B), C5A(C3A,C2A,C1A,C9A,O10A)
5.d Idealised Me refined as rotating group:
 C01X(H01A,H01B,H01C), C01Y(H01D,H01G,H01H), C027(H02A,H02B,H02C), C02B(H02D,
 H02E,H02F), C02G(H02G,H02H,H02I), C02P(H02J,H02L,H02M), C032(H03A,H03B,H03C),
 C036(H03D,H03E,H03F)
;
_shelx_res_checksum              67511
_shelx_fab_checksum              73887
_olex2_submission_special_instructions 'No special instructions were received'