Stepwise reduction of a corannulene-based helical molecular nanographene with Na metal
Zhou, Zheng; Zhu, Yikun; Fernández-García, Jesús M.; Wei, Zheng; Fernández, Israel; Petrukhina, Marina A.; Martín, Nazario; Chemical Communications  (2022) –; doi:10.1039/D2CC00971D

data_7129902
_publ_section_title
;
 Stepwise reduction of a corannulene-based helical molecular nanographene
 with Na metal
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00971D
_journal_year                    2022
_chemical_formula_moiety         'C76 H64, 0.5(C H3 N O2)'
_chemical_formula_sum            'C76.5 H65.5 N0.5 O'
_chemical_formula_weight         1007.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-10-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-18 deposited with the CCDC.	2022-03-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.8220(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.2936(3)
_cell_length_b                   21.0583(4)
_cell_length_c                   17.2056(3)
_cell_measurement_reflns_used    8534
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.81
_cell_measurement_theta_min      3.36
_cell_volume                     5732.56(18)
_computing_cell_refinement       'SAINT V8.38A (bruker, 2016)'
_computing_data_collection       'APEX3 v.2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0868
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            45846
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.260
_diffrn_reflns_theta_min         3.357
_diffrn_source                   'INCOATEC ImuS micro-focus source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.510
_exptl_absorpt_correction_T_max  0.6549
_exptl_absorpt_correction_T_min  0.5018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1283 before and 0.0767 after correction.
The Ratio of minimum to maximum transmission is 0.7662.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_description       block
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     925
_refine_ls_number_reflns         11455
_refine_ls_number_restraints     2306
_refine_ls_restrained_S_all      0.921
_refine_ls_R_factor_all          0.1226
_refine_ls_R_factor_gt           0.0793
_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^)+(0.1331P)^2^+0.5934P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1997
_refine_ls_wR_factor_ref         0.2310
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7086
_reflns_number_total             11455
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00971d2.cif
_cod_data_source_block           1
_cod_original_formula_sum        'C76.50 H65.50 N0.50 O'
_cod_database_code               7129902
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.960
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2-C01H = C024-C01H = C1-C01H = C023-C01H = C3-C01H = C022-C01H
 1.54 with sigma of 0.02
 C0AA-C00Z = C01Z-C00Z = C1AA-C00Z = C021-C00Z = C2AA-C00Z = C020-C00Z
 1.54 with sigma of 0.02
 C00I-C00K \\sim C3AA-C4AA
 with sigma of 0.02
 C00I-C011 \\sim C3AA-C0
 with sigma of 0.02
 C00I-C01E \\sim C3AA-C7AA
 with sigma of 0.02
 C00K-C00M \\sim C4AA-C00M
 with sigma of 0.02
 C00K-C015 \\sim C4AA-C4
 with sigma of 0.02
 C010-C018 \\sim C010-C5
 with sigma of 0.02
 C011-C018 \\sim C0-C5
 with sigma of 0.02
 C011-C01B \\sim C0-C5AA
 with sigma of 0.02
 C015-C01D \\sim C4-C6AA
 with sigma of 0.02
 C018-C01F \\sim C5-C7BA
 with sigma of 0.02
 C01B-C01G \\sim C5AA-C8AA
 with sigma of 0.02
 C01B-C01P \\sim C5AA-C2BA
 with sigma of 0.02
 C01D-C01J \\sim C6AA-C9AA
 with sigma of 0.02
 C01E-C01G \\sim C7AA-C8AA
 with sigma of 0.02
 C01E-C01J \\sim C7AA-C9AA
 with sigma of 0.02
 C01F-C01N \\sim C7BA-C0BA
 with sigma of 0.02
 C01G-C01O \\sim C8AA-C1BA
 with sigma of 0.02
 C01J-C01Q \\sim C9AA-C3BA
 with sigma of 0.02
 C01N-C01P \\sim C0BA-C2BA
 with sigma of 0.02
 C01O-C01T \\sim C1BA-C4BA
 with sigma of 0.02
 C01O-C01U \\sim C1BA-C5BA
 with sigma of 0.02
 C01P-C01W \\sim C2BA-C6BA
 with sigma of 0.02
 C01Q-C01U \\sim C3BA-C5BA
 with sigma of 0.02
 C01T-C01W \\sim C4BA-C6BA
 with sigma of 0.02
 C00I-C00M \\sim C3AA-C00M
 with sigma of 0.04
 C00I-C015 \\sim C3AA-C4
 with sigma of 0.04
 C00I-C018 \\sim C3AA-C5
 with sigma of 0.04
 C00I-C01B \\sim C3AA-C5AA
 with sigma of 0.04
 C00I-C01G \\sim C3AA-C8AA
 with sigma of 0.04
 C00I-C01J \\sim C3AA-C9AA
 with sigma of 0.04
 C00K-C011 \\sim C4AA-C0
 with sigma of 0.04
 C00K-C01D \\sim C4AA-C6AA
 with sigma of 0.04
 C00K-C01E \\sim C4AA-C7AA
 with sigma of 0.04
 C00M-C015 \\sim C00M-C4
 with sigma of 0.04
 C010-C011 \\sim C010-C0
 with sigma of 0.04
 C010-C01F \\sim C010-C7BA
 with sigma of 0.04
 C011-C01E \\sim C0-C7AA
 with sigma of 0.04
 C011-C01F \\sim C0-C7BA
 with sigma of 0.04
 C011-C01G \\sim C0-C8AA
 with sigma of 0.04
 C011-C01P \\sim C0-C2BA
 with sigma of 0.04
 C015-C01J \\sim C4-C9AA
 with sigma of 0.04
 C018-C01B \\sim C5-C5AA
 with sigma of 0.04
 C018-C01N \\sim C5-C0BA
 with sigma of 0.04
 C01B-C01E \\sim C5AA-C7AA
 with sigma of 0.04
 C01B-C01N \\sim C5AA-C0BA
 with sigma of 0.04
 C01B-C01O \\sim C5AA-C1BA
 with sigma of 0.04
 C01B-C01W \\sim C5AA-C6BA
 with sigma of 0.04
 C01D-C01E \\sim C6AA-C7AA
 with sigma of 0.04
 C01D-C01Q \\sim C6AA-C3BA
 with sigma of 0.04
 C01E-C01O \\sim C7AA-C1BA
 with sigma of 0.04
 C01E-C01Q \\sim C7AA-C3BA
 with sigma of 0.04
 C01F-C01P \\sim C7BA-C2BA
 with sigma of 0.04
 C01G-C01J \\sim C8AA-C9AA
 with sigma of 0.04
 C01G-C01P \\sim C8AA-C2BA
 with sigma of 0.04
 C01G-C01T \\sim C8AA-C4BA
 with sigma of 0.04
 C01G-C01U \\sim C8AA-C5BA
 with sigma of 0.04
 C01J-C01U \\sim C9AA-C5BA
 with sigma of 0.04
 C01N-C01W \\sim C0BA-C6BA
 with sigma of 0.04
 C01O-C01Q \\sim C1BA-C3BA
 with sigma of 0.04
 C01O-C01W \\sim C1BA-C6BA
 with sigma of 0.04
 C01P-C01T \\sim C2BA-C4BA
 with sigma of 0.04
 C01T-C01U \\sim C4BA-C5BA
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C6BA \\sim C001 \\sim C003 \\sim C004 \\sim C00A \\sim C002 \\sim C006 \\sim
C005 \\sim C008 \\sim C00L \\sim C00Q \\sim C00O \\sim C00S \\sim C007 \\sim
C00G \\sim C00C \\sim C00H \\sim C00B \\sim C00M \\sim C00W \\sim C00R \\sim
C00N \\sim C00Y \\sim C00E \\sim C009 \\sim C00D \\sim C012 \\sim C00K \\sim
C010 \\sim C4AA \\sim C014 \\sim C00J \\sim C00X \\sim C00F \\sim C00P \\sim
C00U \\sim C016 \\sim C017 \\sim C00I \\sim C015 \\sim C018 \\sim C5 \\sim C3AA
\\sim C4 \\sim C00Z \\sim C013 \\sim C00T \\sim C00V \\sim C019 \\sim C01K
\\sim C01M \\sim C01C \\sim C011 \\sim C01E \\sim C01D \\sim C01F \\sim C0
\\sim C7BA \\sim C7AA \\sim C6AA \\sim C01Z \\sim C020 \\sim C021 \\sim C2AA
\\sim C0AA \\sim C1AA \\sim C01I \\sim C01A \\sim C01V \\sim C01X \\sim C01Y
\\sim C01B \\sim C01G \\sim C01J \\sim C01N \\sim C5AA \\sim C0BA \\sim C8AA
\\sim C9AA \\sim C01L \\sim C01R \\sim C01S \\sim C01H \\sim C01P \\sim C01O
\\sim C01Q \\sim C2BA \\sim C1BA \\sim C3BA \\sim C022 \\sim C023 \\sim C024
\\sim C1 \\sim C2 \\sim C3 \\sim C01W \\sim C01T \\sim C01U \\sim C4BA \\sim
C5BA: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 C01W, C001, C003, C004, C00A, C002, C006, C005, C008, C00L, C00Q, C00O, C00S,
 C007, C00G, C00C, C00H, C00B, C00M, C00W, C00R, C00N, C00Y, C00E, C009, C00D,
 C012, C00K, C010, C4AA, C014, C00J, C00X, C00F, C00P, C00U, C016, C017, C00I,
 C015, C018, C5, C3AA, C4, C00Z, C013, C00T, C00V, C019, C01K, C01M, C01C, C011,
  C01E, C01D, C01F, C0, C7BA, C7AA, C6AA, C01Z, C020, C021, C2AA, C0AA, C1AA,
 C01I, C01A, C01V, C01X, C01Y, C01B, C01G, C01J, C01N, C5AA, C0BA, C8AA, C9AA,
 C01L, C01R, C01S, C01H, C01P, C01O, C01Q, C2BA, C1BA, C3BA, C022, C023, C024,
 C1, C2, C3, C01T, C01U, C6BA, C4BA, C5BA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=Sof(C3)=
 Sof(H3A)=Sof(H3B)=Sof(H3C)=1-FVAR(1)
 Sof(C022)=Sof(H02G)=Sof(H02H)=Sof(H02I)=Sof(C023)=Sof(H02J)=Sof(H02K)=
 Sof(H02L)=Sof(C024)=Sof(H02M)=Sof(H02N)=Sof(H02O)=FVAR(1)
 Sof(C2AA)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=Sof(C0AA)=Sof(H0AB)=Sof(H0AC)=
 Sof(H0AD)=Sof(C1AA)=Sof(H1AB)=Sof(H1AC)=Sof(H1AD)=1-FVAR(2)
 Sof(C01Z)=Sof(H1AA)=Sof(HF)=Sof(HG)=Sof(C020)=Sof(H02A)=Sof(H02B)=Sof(H02C)=
 Sof(C021)=Sof(H02D)=Sof(H02E)=Sof(H02F)=FVAR(2)
 Sof(C3AA)=Sof(C4AA)=Sof(C0)=Sof(C4)=Sof(H4)=Sof(C5AA)=Sof(C6AA)=Sof(H6AA)=
 Sof(C7AA)=Sof(C8AA)=Sof(C9AA)=Sof(C0BA)=Sof(H0BA)=Sof(C1BA)=Sof(C2BA)=
 Sof(C3BA)=Sof(H3BA)=Sof(C4BA)=Sof(H4BA)=Sof(C5BA)=Sof(H5BA)=Sof(C6BA)=
 Sof(H6BA)=Sof(C5)=Sof(C7BA)=Sof(H7BA)=1-FVAR(3)
 Sof(C00I)=Sof(C00K)=Sof(C011)=Sof(C015)=Sof(H015)=Sof(C018)=Sof(C01B)=
 Sof(C01D)=Sof(H01D)=Sof(C01E)=Sof(C01F)=Sof(H01F)=Sof(C01G)=Sof(C01J)=
 Sof(C01N)=Sof(H01O)=Sof(C01O)=Sof(C01P)=Sof(C01Q)=Sof(H01Q)=Sof(C01T)=
 Sof(H01W)=Sof(C01U)=Sof(H01X)=Sof(C01W)=Sof(H01Z)=FVAR(3)
6.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00P(H00P), C00R(H00R), C00T(H00T), C00U(H00U),
 C00V(H00V), C00X(H00X), C00Y(H00Y), C012(H012), C014(H014), C015(H015),
 C01D(H01D), C01F(H01F), C01N(H01O), C01Q(H01Q), C01T(H01W), C01U(H01X),
 C01W(H01Z), C4(H4), C6AA(H6AA), C0BA(H0BA), C3BA(H3BA), C4BA(H4BA), C5BA(H5BA),
  C6BA(H6BA), C7BA(H7BA)
6.b Idealised Me refined as rotating group:
 C019(H01A,H01B,H01C), C01K(H01E,H01G,H01H), C01L(H01I,H01J,H01K), C01M(H01L,
 H01M,H01N), C01R(H01P,H01R,H01S), C01S(H01T,H01U,H01V), C01V(H01Y,H,HA),
 C01X(H01,HB,HC), C01Y(H0AA,HD,HE), C01Z(H1AA,HF,HG), C020(H02A,H02B,H02C),
 C021(H02D,H02E,H02F), C022(H02G,H02H,H02I), C023(H02J,H02K,H02L), C024(H02M,
 H02N,H02O), C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C2AA(H2AA,H2AB,
 H2AC), C0AA(H0AB,H0AC,H0AD), C1AA(H1AB,H1AC,H1AD)
;
_shelx_res_checksum              35824
_shelx_fab_checksum              39009
_olex2_submission_special_instructions 'No special instructions were received'