Pentacosacyclenes: cruciform molecular nanocarbons based on cyclooctatetraene.
Kumar, Rakesh; Chmielewski, Piotr J.; Lis, Tadeusz; Czarnecki, Mirosław; Stępień, Marcin; Chemical science 15 (2024) 18640–18649; doi:10.1039/d4sc05938g

data_1572862
_publ_section_title
;
 Pentacosacyclenes: cruciform molecular nanocarbons based on
 cyclooctatetraene.
;
_journal_issue                   44
_journal_name_full               'Chemical science'
_journal_page_first              18640
_journal_page_last               18649
_journal_paper_doi               10.1039/d4sc05938g
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C144 H100 N4 O8, 14(C7 H8)'
_chemical_formula_sum            'C242 H212 N4 O8'
_chemical_formula_weight         3304.14
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2023-10-11
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-09-02 deposited with the CCDC.	2024-10-08 downloaded from the CCDC.
;
_cell_angle_alpha                69.30(2)
_cell_angle_beta                 84.33(2)
_cell_angle_gamma                76.83(2)
_cell_formula_units_Z            2
_cell_length_a                   16.846(2)
_cell_length_b                   22.876(6)
_cell_length_c                   25.515(4)
_cell_measurement_reflns_used    33935
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      45
_cell_measurement_theta_min      1.8
_cell_volume                     8954(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            55865
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         73.917
_diffrn_reflns_theta_min         1.851
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.559
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark violet'
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_description       plate
_exptl_crystal_F_000             3512
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.765
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.246
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1880
_refine_ls_number_reflns         55865
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.250
_refine_ls_R_factor_all          0.1709
_refine_ls_R_factor_gt           0.1195
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.2000P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3290
_refine_ls_wR_factor_ref         0.3687
_reflns_Friedel_coverage         0.000
_reflns_number_gt                31752
_reflns_number_total             55865
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc05938g3.cif
_cod_data_source_block           rk245t
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'direct methods' was
changed to 'direct'.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1572861--1572863.cif.
;
_cod_database_code               1572862
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.833
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.61462
 0.38538
2. Restrained distances
 C1E-C7E
 1.5 with sigma of 0.01
 C1G-C7G = C1F-C7F
 1.5 with sigma of 0.01
 C1J-C7J
 1.5 with sigma of 0.01
 C1K-C7K
 1.5 with sigma of 0.01
 C7L-C2L
 2.5 with sigma of 0.02
 C1M-C7M
 1.5 with sigma of 0.02
 C6M-C7M = C2M-C7M
 2.45 with sigma of 0.02
 C7N-C1N = C7N1-C1N1
 1.5 with sigma of 0.01
 C1O-C7O = C1O1-C7O1
 1.5 with sigma of 0.01
 C2P-C7P
 2.5 with sigma of 0.02
 C1P-C7P = C1P1-C7P1
 1.54 with sigma of 0.01
 C1Q-C7Q = C1Q1-C7Q1
 1.5 with sigma of 0.01
 C2Q-C7Q = C6Q-C7Q = C2Q1-C7Q1 = C6Q1-C7Q1
 2.45 with sigma of 0.02
 C7S-C1S
 1.5 with sigma of 0.01
 C7S-C2S = C7S-C6S
 2.45 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uiso(C1M) = Uiso(C2M) = Uiso(C3M) = Uiso(C4M) = Uiso(C5M) = Uiso(C6M)
Uiso(C1O) = Uiso(C2O) = Uiso(C3O) = Uiso(C4O) = Uiso(C5O) = Uiso(C6O) =
Uiso(C7O) = Uiso(C1O1) = Uiso(C2O1) = Uiso(C3O1) = Uiso(C4O1) = Uiso(C5O1) =
Uiso(C6O1) = Uiso(C7O1)
Uiso(C1P) = Uiso(C2P) = Uiso(C3P) = Uiso(C4P) = Uiso(C5P) = Uiso(C6P) =
Uiso(C7P) = Uiso(C1P1) = Uiso(C2P1) = Uiso(C3P1) = Uiso(C4P1) = Uiso(C5P1) =
Uiso(C6P1) = Uiso(C7P1)
Uiso(C1Q) = Uiso(C2Q) = Uiso(C3Q) = Uiso(C4Q) = Uiso(C5Q) = Uiso(C6Q) =
Uiso(C7Q) = Uiso(C1Q1) = Uiso(C2Q1) = Uiso(C3Q1) = Uiso(C4Q1) = Uiso(C5Q1) =
Uiso(C6Q1) = Uiso(C7Q1)
Uiso(C1S) = Uiso(C2S) = Uiso(C3S) = Uiso(C4S) = Uiso(C5S) = Uiso(C6S) =
Uiso(C7S)
4. Others
 Fixed Sof: C1H(0.5) C2H(0.5) H2H(0.5) C3H(0.5) H3H(0.5) C4H(0.5) H4H(0.5)
 C5H(0.5) H5H(0.5) C6H(0.5) H6H(0.5) C7H(0.5) H7H1(0.5) H7H2(0.5) H7H3(0.5)
 C1H1(0.5) C2H1(0.5) H2H1(0.5) C3H1(0.5) H3H1(0.5) C4H1(0.5) H4H1(0.5)
 C5H1(0.5) H5H1(0.5) C6H1(0.5) H6H1(0.5) C7H1(0.5) H7H4(0.5) H7H5(0.5)
 H7H6(0.5) C1I(0.5) C2I(0.5) H2I(0.5) C3I(0.5) H3I(0.5) C4I(0.5) H4I(0.5)
 C5I(0.5) H5I(0.5) C6I(0.5) H6I(0.5) C7I(0.5) H7I1(0.5) H7I2(0.5) H7I3(0.5)
 C1I1(0.5) C2I1(0.5) H2I1(0.5) C3I1(0.5) H3I1(0.5) C4I1(0.5) H4I1(0.5)
 C5I1(0.5) H5I1(0.5) C6I1(0.5) H6I1(0.5) C7I1(0.5) H7I4(0.5) H7I5(0.5)
 H7I6(0.5) C1K(0.5) C2K(0.5) H2K(0.5) C3K(0.5) H3K(0.5) C4K(0.5) H4K(0.5)
 C5K(0.5) H5K(0.5) C6K(0.5) H6K(0.5) C7K(0.5) H7K1(0.5) H7K2(0.5) H7K3(0.5)
 C1K1(0.5) C2K1(0.5) H2K1(0.5) C3K1(0.5) H3K1(0.5) C4K1(0.5) H4K1(0.5)
 C5K1(0.5) H5K1(0.5) C6K1(0.5) H6K1(0.5) C7K1(0.5) H7K4(0.5) H7K5(0.5)
 H7K6(0.5) C1L(0.5) C2L(0.5) H2L(0.5) C3L(0.5) H3L(0.5) C4L(0.5) H4L(0.5)
 C5L(0.5) H5L(0.5) C6L(0.5) H6L(0.5) C7L(0.5) H7L1(0.5) H7L2(0.5) H7L3(0.5)
 C1L1(0.5) C2L1(0.5) H2L1(0.5) C3L1(0.5) H3L1(0.5) C4L1(0.5) H4L1(0.5)
 C5L1(0.5) H5L1(0.5) C6L1(0.5) H6L1(0.5) C7L1(0.5) H7L4(0.5) H7L5(0.5)
 H7L6(0.5) C1M(0.5) C2M(0.5) H2M(0.5) C3M(0.5) H3M(0.5) C4M(0.5) H4M(0.5)
 C5M(0.5) H5M(0.5) C6M(0.5) H6M(0.5) C7M(0.5) H7M1(0.5) H7M2(0.5) H7M3(0.5)
 C1M1(0.5) C2M1(0.5) H2M1(0.5) C3M1(0.5) H3M1(0.5) C4M1(0.5) H4M1(0.5)
 C5M1(0.5) H5M1(0.5) C6M1(0.5) H6M1(0.5) C7M1(0.5) H7M4(0.5) H7M5(0.5)
 H7M6(0.5) C1N(0.5) C2N(0.5) H2N(0.5) C3N(0.5) H3N(0.5) C4N(0.5) H4N(0.5)
 C5N(0.5) H5N(0.5) C6N(0.5) H6N(0.5) C7N(0.5) H7N1(0.5) H7N2(0.5) H7N3(0.5)
 C1N1(0.5) C2N1(0.5) H2N1(0.5) C3N1(0.5) H3N1(0.5) C4N1(0.5) H4N1(0.5)
 C5N1(0.5) H5N1(0.5) C6N1(0.5) H6N1(0.5) C7N1(0.5) H7N4(0.5) H7N5(0.5)
 H7N6(0.5) C1O(0.5) C2O(0.5) H2O(0.5) C3O(0.5) H3O(0.5) C4O(0.5) H4O(0.5)
 C5O(0.5) H5O(0.5) C6O(0.5) H6O(0.5) C7O(0.5) H7O1(0.5) H7O2(0.5) H7O3(0.5)
 C1O1(0.5) C2O1(0.5) H2O1(0.5) C3O1(0.5) H3O1(0.5) C4O1(0.5) H4O1(0.5)
 C5O1(0.5) H5O1(0.5) C6O1(0.5) H6O1(0.5) C7O1(0.5) H7O4(0.5) H7O5(0.5)
 H7O6(0.5) C1P(0.5) C2P(0.5) H2P(0.5) C3P(0.5) H3P(0.5) C4P(0.5) H4P(0.5)
 C5P(0.5) H5P(0.5) C6P(0.5) H6P(0.5) C7P(0.5) H7P1(0.5) H7P2(0.5) H7P3(0.5)
 C1P1(0.5) C2P1(0.5) H2P1(0.5) C3P1(0.5) H3P1(0.5) C4P1(0.5) H4P1(0.5)
 C5P1(0.5) H5P1(0.5) C6P1(0.5) H6P1(0.5) C7P1(0.5) H7P4(0.5) H7P5(0.5)
 H7P6(0.5) C1Q(0.5) C2Q(0.5) H2Q(0.5) C3Q(0.5) H3Q(0.5) C4Q(0.5) H4Q(0.5)
 C5Q(0.5) H5Q(0.5) C6Q(0.5) H6Q(0.5) C7Q(0.5) H7Q1(0.5) H7Q2(0.5) H7Q3(0.5)
 C1Q1(0.5) C2Q1(0.5) H2Q1(0.5) C3Q1(0.5) H3Q1(0.5) C4Q1(0.5) H4Q1(0.5)
 C5Q1(0.5) H5Q1(0.5) C6Q1(0.5) H6Q1(0.5) C7Q1(0.5) H7Q4(0.5) H7Q5(0.5)
 H7Q6(0.5) C1R(0.5) C2R(0.5) H2R(0.5) C3R(0.5) H3R(0.5) C4R(0.5) H4R(0.5)
 C5R(0.5) H5R(0.5) C6R(0.5) H6R(0.5) C7R(0.5) H7R1(0.5) H7R2(0.5) H7R3(0.5)
 C1S(0.5) C2S(0.5) H2S(0.5) C3S(0.5) H3S(0.5) C4S(0.5) H4S(0.5) C5S(0.5)
 H5S(0.5) C6S(0.5) H6S(0.5) C7S(0.5) H7S1(0.5) H7S2(0.5) H7S3(0.5)
5.a Riding coordinates:
 C7E(H7E1,H7E2,H7E3), C7F(H7F1,H7F2,H7F3), C7G(H7G1,H7G2,H7G3), C7H(H7H1,H7H2,
 H7H3), C7H1(H7H4,H7H5,H7H6), C7I(H7I1,H7I2,H7I3), C7I1(H7I4,H7I5,H7I6),
 C7J(H7J1,H7J2,H7J3), C7K(H7K1,H7K2,H7K3), C7K1(H7K4,H7K5,H7K6), C7L(H7L1,H7L2,
 H7L3), C7L1(H7L4,H7L5,H7L6), C7M(H7M1,H7M2,H7M3), C7M1(H7M4,H7M5,H7M6),
 C7N(H7N1,H7N2,H7N3), C7N1(H7N4,H7N5,H7N6), C7O(H7O1,H7O2,H7O3), C7O1(H7O4,H7O5,
 H7O6), C7P(H7P1,H7P2,H7P3), C7P1(H7P4,H7P5,H7P6), C7Q(H7Q1,H7Q2,H7Q3),
 C7Q1(H7Q4,H7Q5,H7Q6), C7R(H7R1,H7R2,H7R3), C7S(H7S1,H7S2,H7S3)
5.b Ternary CH refined with riding coordinates:
 C31A(H31A), C34A(H34A), C31B(H31B), C34B(H34B), C31C(H31C), C34C(H34C),
 C31D(H31D), C34D(H34D)
5.c Me refined with riding coordinates:
 C32A(H32A,H32B,H32C), C33A(H33A,H33B,H33C), C35A(H35A,H35B,H35C), C36A(H36A,
 H36B,H36C), C32B(H32D,H32E,H32F), C33B(H33D,H33E,H33F), C35B(H35D,H35E,H35F),
 C36B(H36D,H36E,H36F), C32C(H32G,H32H,H32I), C33C(H33G,H33H,H33I), C35C(H35G,
 H35H,H35I), C36C(H36G,H36H,H36I), C32D(H32J,H32K,H32L), C33D(H33J,H33K,H33L),
 C35D(H35J,H35K,H35L), C36D(H36J,H36K,H36L)
5.d Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C6A(H6A), C9A(H9A), C10A(H10A), C14A(H14A), C15A(H15A), C18A(H18A),
 C19A(H19A), C27A(H27A), C28A(H28A), C29A(H29A), C5B(H5B), C6B(H6B), C9B(H9B),
 C10B(H10B), C14B(H14B), C15B(H15B), C18B(H18B), C19B(H19B), C27B(H27B),
 C28B(H28B), C29B(H29B), C5C(H5C), C6C(H6C), C9C(H9C), C10C(H10C), C14C(H14C),
 C15C(H15C), C18C(H18C), C19C(H19C), C27C(H27C), C28C(H28C), C29C(H29C),
 C5D(H5D), C6D(H6D), C9D(H9D), C10D(H10D), C14D(H14D), C15D(H15D), C18D(H18D),
 C19D(H19D), C27D(H27D), C28D(H28D), C29D(H29D), C2E(H2E), C3E(H3E), C4E(H4E),
 C5E(H5E), C6E(H6E), C2F(H2F), C3F(H3F), C4F(H4F), C5F(H5F), C6F(H6F), C2G(H2G),
  C3G(H3G), C4G(H4G), C5G(H5G), C6G(H6G), C2H(H2H), C3H(H3H), C4H(H4H),
 C5H(H5H), C6H(H6H), C2H1(H2H1), C3H1(H3H1), C4H1(H4H1), C5H1(H5H1), C6H1(H6H1),
  C2I(H2I), C3I(H3I), C4I(H4I), C5I(H5I), C6I(H6I), C2I1(H2I1), C3I1(H3I1),
 C4I1(H4I1), C5I1(H5I1), C6I1(H6I1), C2J(H2J), C3J(H3J), C4J(H4J), C5J(H5J),
 C6J(H6J), C2K(H2K), C3K(H3K), C4K(H4K), C5K(H5K), C6K(H6K), C2K1(H2K1),
 C3K1(H3K1), C4K1(H4K1), C5K1(H5K1), C6K1(H6K1), C2L(H2L), C3L(H3L), C4L(H4L),
 C5L(H5L), C6L(H6L), C2L1(H2L1), C3L1(H3L1), C4L1(H4L1), C5L1(H5L1), C6L1(H6L1),
  C2M(H2M), C3M(H3M), C4M(H4M), C5M(H5M), C6M(H6M), C2M1(H2M1), C3M1(H3M1),
 C4M1(H4M1), C5M1(H5M1), C6M1(H6M1), C2N(H2N), C3N(H3N), C4N(H4N), C5N(H5N),
 C6N(H6N), C2N1(H2N1), C3N1(H3N1), C4N1(H4N1), C5N1(H5N1), C6N1(H6N1), C2O(H2O),
  C3O(H3O), C4O(H4O), C5O(H5O), C6O(H6O), C2O1(H2O1), C3O1(H3O1), C4O1(H4O1),
 C5O1(H5O1), C6O1(H6O1), C2P(H2P), C3P(H3P), C4P(H4P), C5P(H5P), C6P(H6P),
 C2P1(H2P1), C3P1(H3P1), C4P1(H4P1), C5P1(H5P1), C6P1(H6P1), C2Q(H2Q), C3Q(H3Q),
  C4Q(H4Q), C5Q(H5Q), C6Q(H6Q), C2Q1(H2Q1), C3Q1(H3Q1), C4Q1(H4Q1), C5Q1(H5Q1),
 C6Q1(H6Q1), C2R(H2R), C3R(H3R), C4R(H4R), C5R(H5R), C6R(H6R), C2S(H2S),
 C3S(H3S), C4S(H4S), C5S(H5S), C6S(H6S)
5.e Fitted hexagon refined as free rotating group:
 C1E(C2E,C3E,C4E,C5E,C6E), C1F(C2F,C3F,C4F,C5F,C6F), C1G(C2G,C3G,C4G,C5G,C6G),
 C1H(C2H,C3H,C4H,C5H,C6H), C1H1(C2H1,C3H1,C4H1,C5H1,C6H1), C1I(C2I,C3I,C4I,C5I,
 C6I), C1I1(C2I1,C3I1,C4I1,C5I1,C6I1), C1J(C2J,C3J,C4J,C5J,C6J), C1K(C2K,C3K,
 C4K,C5K,C6K), C1K1(C2K1,C3K1,C4K1,C5K1,C6K1), C1L(C2L,C3L,C4L,C5L,C6L),
 C1L1(C2L1,C3L1,C4L1,C5L1,C6L1), C1M(C2M,C3M,C4M,C5M,C6M), C1M1(C2M1,C3M1,C4M1,
 C5M1,C6M1), C1N(C2N,C3N,C4N,C5N,C6N), C1N1(C2N1,C3N1,C4N1,C5N1,C6N1), C1O(C2O,
 C3O,C4O,C5O,C6O), C1O1(C2O1,C3O1,C4O1,C5O1,C6O1), C1P(C2P,C3P,C4P,C5P,C6P),
 C1P1(C2P1,C3P1,C4P1,C5P1,C6P1), C1Q(C2Q,C3Q,C4Q,C5Q,C6Q), C1Q1(C2Q1,C3Q1,C4Q1,
 C5Q1,C6Q1), C1R(C2R,C3R,C4R,C5R,C6R), C1S(C2S,C3S,C4S,C5S,C6S)
;
_shelx_res_checksum              10981
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.861
_oxdiff_exptl_absorpt_empirical_full_min 0.635