Isolable GaN-based analogues of Thiele's and Chichibabin's hydrocarbons
Jiang, Yuqi; Pan, Guo; Zhou, Ren; Huang, Ruihao; Ran, Dongmei; Xu, Daqian; Su, Yuanting; Chemical Communications 61 (2025) 8192–8195; doi:10.1039/D5CC01531F

data_7134472
_publ_section_title
;
 Isolable GaN-based analogues of Thiele's and Chichibabin's hydrocarbons
;
_journal_issue                   45
_journal_name_full               'Chemical Communications'
_journal_page_first              8192
_journal_page_last               8195
_journal_paper_doi               10.1039/D5CC01531F
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C64 H96 Ga2 N2'
_chemical_formula_sum            'C64 H96 Ga2 N2'
_chemical_formula_weight         1032.86
_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
_audit_creation_date             2023-12-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-03-06 deposited with the CCDC.	2025-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                107.74(3)
_cell_angle_beta                 103.724(19)
_cell_angle_gamma                102.71(3)
_cell_formula_units_Z            1
_cell_length_a                   9.926(5)
_cell_length_b                   12.299(11)
_cell_length_c                   14.106(9)
_cell_measurement_reflns_used    149
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      23.55
_cell_measurement_theta_min      4.81
_cell_volume                     1511.7(19)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker D8 Venture diffractometer'
_computing_data_reduction        'SAINT V8.40B (?, 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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0934
_diffrn_reflns_av_unetI/netI     0.0681
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25050
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.176
_diffrn_reflns_theta_max         25.176
_diffrn_reflns_theta_min         2.278
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.928
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.3231
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1901 before and 0.1148 after correction.
The Ratio of minimum to maximum transmission is 0.4336.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            reddish
_exptl_crystal_colour_primary    reddish
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_description       block
_exptl_crystal_F_000             556
_exptl_crystal_recrystallization_method
'The crystals were growth by means of evaporation of a mixture of n-hexane and toluene at RT.'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.765
_refine_diff_density_rms         0.130
_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     512
_refine_ls_number_reflns         5328
_refine_ls_number_restraints     630
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0572
_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^)+(0.1095P)^2^+0.8819P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1691
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4476
_reflns_number_total             5328
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01531f2.cif
_cod_data_source_block           Compound3
_cod_depositor_comments
'Adding full bibliography for 7134471--7134474.cif.'
_cod_original_cell_volume        1511.8(18)
_cod_database_code               7134472
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.889
_shelx_estimated_absorpt_t_min   0.851
_exptl_crystal_mounting_method
'Crystals were removed from the crystallisation vial and immediately coated with polybutenes oil (CAS: 9003-29-6) on a glass slide. A suitable single crystal coated with polybutenes oil as less as possible was sealed in capillary tube filled with argon. The capillary tube with single crystal was mounted on copper pin with solid paraffin.'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C21 \\sim C30 \\sim C31 \\sim C32 \\sim C30A \\sim C31A \\sim C32A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02
C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9 \\sim C11 \\sim C12
\\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17 \\sim C3A \\sim C4A \\sim C5A
\\sim C6A \\sim C7A \\sim C8A \\sim C11A \\sim C12A \\sim C13A \\sim C14A \\sim
C15A \\sim C16A \\sim C17A \\sim C10 \\sim C9A \\sim C10A \\sim Ga1: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02
C27 \\sim C28 \\sim C29 \\sim C28A \\sim C29A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
3. Same fragment restrains
{Ga1, C3A, C4A, C5A, C6A, C7A, C8A, C9A, C10A, C11A, C12A, C13A, C14A, C15A,
C16A, C17A} sigma for 1-2: 0.02, 1-3: 0.04
as
{Ga1, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17}
{C21, C30A, C31A, C32A} sigma for 1-2: 0.02, 1-3: 0.04
as
{C21, C30, C31, C32}
{C27, C28A, C29A} sigma for 1-2: 0.02, 1-3: 0.04
as
{C27, C28, C29}
4. Others
 Sof(C3A)=Sof(C4A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=
 Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10D)=Sof(H10E)=Sof(H10F)=Sof(C11A)=Sof(H11D)=
 Sof(H11E)=Sof(H11F)=Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(H13D)=Sof(H13E)=
 Sof(H13F)=Sof(C14A)=Sof(H14D)=Sof(H14E)=Sof(H14F)=Sof(C15A)=Sof(H15A)=
 Sof(C16A)=Sof(H16D)=Sof(H16E)=Sof(H16F)=Sof(C17A)=Sof(H17D)=Sof(H17E)=
 Sof(H17F)=1-FVAR(1)
 Sof(C3)=Sof(C4)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(C9)=
 Sof(H9)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=Sof(C11)=Sof(H11A)=Sof(H11B)=
 Sof(H11C)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=Sof(C14)=
 Sof(H14A)=Sof(H14B)=Sof(H14C)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16A)=Sof(H16B)=
 Sof(H16C)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=FVAR(1)
 Sof(H27A)=Sof(C28A)=Sof(H28D)=Sof(H28E)=Sof(H28F)=Sof(C29A)=Sof(H29D)=
 Sof(H29E)=Sof(H29F)=1-FVAR(2)
 Sof(H27)=Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=Sof(C29)=Sof(H29A)=Sof(H29B)=
 Sof(H29C)=FVAR(2)
 Sof(C30A)=Sof(H30A)=Sof(C31A)=Sof(H31D)=Sof(H31E)=Sof(H31F)=Sof(C32A)=
 Sof(H32D)=Sof(H32E)=Sof(H32F)=1-FVAR(3)
 Sof(C30)=Sof(H30)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)=Sof(C32)=Sof(H32A)=
 Sof(H32B)=Sof(H32C)=FVAR(3)
5.a Ternary CH refined with riding coordinates:
 C9(H9), C12(H12), C15(H15), C30(H30), C24(H24), C27(H27), C27(H27A), C9A(H9A),
  C12A(H12A), C15A(H15A), C30A(H30A)
5.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C1(H1), C2(H2), C20(H20), C22(H22), C5A(H5A), C7A(H7A)
5.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C31(H31A,H31B,H31C), C32(H32A,
 H32B,H32C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C28(H28A,H28B,H28C),
 C29(H29A,H29B,H29C), C10A(H10D,H10E,H10F), C11A(H11D,H11E,H11F), C13A(H13D,
 H13E,H13F), C14A(H14D,H14E,H14F), C16A(H16D,H16E,H16F), C17A(H17D,H17E,H17F),
 C28A(H28D,H28E,H28F), C29A(H29D,H29E,H29F), C31A(H31D,H31E,H31F), C32A(H32D,
 H32E,H32F)
;
_shelx_res_checksum              89550
_shelx_hkl_checksum              21998
_olex2_submission_special_instructions 'No special instructions were received'