Synthesis and electronic properties of nitrogen-rich nanographene.
Heim, Gavin P.; Hirahara, Masanari; Dev, Vidhya M.; Agapie, Theodor; Chemical communications (Cambridge, England) 60 (2024) 7343–7346; doi:10.1039/d4cc01189a

data_7133172
_publ_section_title
;
 Synthesis and electronic properties of nitrogen-rich nanographene.
;
_journal_issue                   57
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7343
_journal_page_last               7346
_journal_paper_doi               10.1039/d4cc01189a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         '2.95(C H Cl3), C115.03 H123.74 N12'
_chemical_formula_sum            'C116.94 H127.44 Cl8.84 N12'
_chemical_formula_weight         2014.29
_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     iterative
_audit_creation_date             2023-05-23
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-02-24 deposited with the CCDC.	2024-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                110.586(3)
_cell_angle_beta                 101.322(3)
_cell_angle_gamma                93.081(3)
_cell_formula_units_Z            2
_cell_length_a                   14.3540(6)
_cell_length_b                   18.2341(6)
_cell_length_c                   23.2636(10)
_cell_measurement_reflns_used    9126
_cell_measurement_temperature    175(2)
_cell_measurement_theta_max      34.89
_cell_measurement_theta_min      2.27
_cell_volume                     5538.9(4)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      175.0
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0584
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            86784
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        66.634
_diffrn_reflns_theta_max         66.634
_diffrn_reflns_theta_min         2.672
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.448
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5553
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1189 before and 0.0814 after correction.
The Ratio of minimum to maximum transmission is 0.7367.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_description       Block
_exptl_crystal_F_000             2127
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.297
_refine_diff_density_min         -0.748
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1389
_refine_ls_number_reflns         19324
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0713
_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^)+(0.1148P)^2^+4.5406P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1920
_refine_ls_wR_factor_ref         0.2197
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13721
_reflns_number_total             19324
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01189a2.cif
_cod_data_source_block           v19022
_cod_depositor_comments          'Adding full bibliography for 7133172.cif.'
_cod_database_code               7133172
_shelx_shelxl_version_number     2018/3
_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
 C023-C03D \\sim C023-C03I \\sim C023-C03M \\sim C03D-C03I \\sim C03D-C03M
\\sim C03I-C03M
 with sigma of 0.04
 C02K-C023 \\sim C02K-C03D \\sim C02K-C03I \\sim C02K-C03M \\sim C02K-C2 \\sim
C02K-C4AA \\sim C02K-C3AA
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C3AA, C2, C4AA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C03I, C03M, C03D
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(Cl01)=Sof(Cl02)=Sof(Cl06)=Sof(C03L)=Sof(H2BA)=FVAR(1)
 Sof(H038)=Sof(C4A)=Sof(H4AB)=Sof(H4AC)=Sof(H4AD)=1-FVAR(2)
 Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(H4C)=FVAR(2)
 Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(H13F)=1-FVAR(3)
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=FVAR(3)
 Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=FVAR(4)
 Sof(H1AA)=Sof(HK)=Sof(HL)=Sof(H6AA)=Sof(HU)=Sof(HV)=Sof(H8AA)=Sof(HY)=Sof(HZ)=
 1-FVAR(5)
 Sof(C2)=Sof(C4AA)=Sof(C3AA)=FVAR(5)
 Sof(H7AA)=Sof(HW)=Sof(HX)=Sof(H9AA)=Sof(H5BA)=Sof(H6BA)=Sof(H0BA)=Sof(H7BA)=
 Sof(H8BA)=1-FVAR(6)
 Sof(C5AA)=Sof(H5AB)=Sof(C6AA)=Sof(C17)=FVAR(6)
 Fixed Sof: H0AA(0.5) C03Q(0.5) H1BA(0.5) H9BA(0.5) H0CA(0.5) C3(0.5) H3A(0.5)
 H3B(0.5) H3C(0.5) C6(0.5) H6A(0.5) H6B(0.5) H6C(0.5) C0AA(0.5) H0AB(0.5)
 H0AC(0.5) H0AD(0.5) C1AA(0.5) H1AB(0.5) H1AC(0.5) H1AD(0.5) C2AA(0.5)
 H2AB(0.5) H2AC(0.5) H2AD(0.5)
5.a Ternary CH refined with riding coordinates:
 C02Z(H0AA), C038(H038), C03C(H3BA), C03K(H4BA), C03L(H2BA)
5.b Aromatic/amide H refined with riding coordinates:
 C00Q(H00Q), C015(H015), C017(H017), C01D(H01D), C01I(H01I), C01R(H01R),
 C01U(H01U), C01W(H01W), C01Y(H01Y), C01Z(H01Z), C021(H021), C022(H022),
 C026(H026), C02A(H02D), C02E(H02H), C02F(H02I), C02I(H02J), C02M(H02M),
 C5AA(H5AB)
5.c Idealised Me refined as rotating group:
 C028(H02A,H02B,H02C), C02C(H02E,H02F,H02G), C02O(H02K,H02L,H02N), C02Q(H02O,
 H02P,H02Q), C02R(H02R,H02S,H02T), C02S(H02U,H02V,H02W), C02V(H02X,H02Y,H),
 C02W(H02Z,HA,HB), C02Y(H02,HC,HD), C030(H03A,H03B,H03C), C031(H03D,H03E,H03F),
 C032(H03G,H03H,H03I), C033(H03J,H03K,H03L), C034(H03M,H03N,H03O), C035(H03P,
 H03Q,H03R), C036(H03S,H03T,H03U), C037(H03V,H03W,H03X), C039(H03Y,HE,HF),
 C03A(H03Z,HG,HH), C03B(H03,HI,HJ), C03D(H1AA,HK,HL), C03E(H2AA,HM,HN),
 C03F(H3AA,HO,HP), C03G(H4AA,HQ,HR), C03H(H5AA,HS,HT), C03I(H6AA,HU,HV),
 C03J(H7AA,HW,HX), C03M(H8AA,HY,HZ), C03N(H9AA,H5BA,H6BA), C03O(H0BA,H7BA,H8BA),
  C03Q(H1BA,H9BA,H0CA), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C6(H6A,H6B,H6C),
 C9(H9A,H9B,H9C), C4A(H4AB,H4AC,H4AD), C0AA(H0AB,H0AC,H0AD), C13(H13A,H13B,
 H13C), C13A(H13D,H13E,H13F), C1AA(H1AB,H1AC,H1AD), C2AA(H2AB,H2AC,H2AD)
;
_shelx_res_checksum              80147
_shelx_hkl_checksum              48698
_olex2_submission_special_instructions 'No special instructions were received'