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_7134474
_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         'C70 H100 Cl2 Ga2 N2'
_chemical_formula_sum            'C70 H100 Cl2 Ga2 N2'
_chemical_formula_weight         1179.85
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-12-17
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-03-06 deposited with the CCDC.	2025-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.6669(6)
_cell_length_b                   18.6669(6)
_cell_length_c                   39.267(3)
_cell_measurement_reflns_used    9929
_cell_measurement_temperature    150
_cell_measurement_theta_max      24.85
_cell_measurement_theta_min      2.42
_cell_volume                     13682.7(12)
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.1184
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            68719
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.028
_diffrn_reflns_theta_max         25.028
_diffrn_reflns_theta_min         2.586
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.904
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5505
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1548 before and 0.0948 after correction.
The Ratio of minimum to maximum transmission is 0.7387.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_description       block
_exptl_crystal_F_000             5040
_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          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         2.173
_refine_diff_density_min         -0.864
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         6037
_refine_ls_number_restraints     252
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0745
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0952P)^2^+130.7516P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1927
_refine_ls_wR_factor_ref         0.2155
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4575
_reflns_number_total             6037
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01531f2.cif
_cod_data_source_block           Compound2
_cod_depositor_comments
'Adding full bibliography for 7134471--7134474.cif.'
_cod_original_cell_volume        13682.5(12)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               7134474
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.915
_shelx_estimated_absorpt_t_min   0.892
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C26 \\sim C33 \\sim C34 \\sim C35 \\sim C33A \\sim C34A \\sim C35A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C9 \\sim C15 \\sim C16 \\sim C17 \\sim C15A \\sim C16A \\sim C17A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C24 \\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 within 2A
3. Same fragment restrains
{C26, C33A, C34A, C35A} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C26, C33, C34, C35}
{C24, C30A, C31A, C32A} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C24, C30, C31, C32}
{C9, C15A, C16A, C17A} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C9, C15, C16, C17}
4. Others
 Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16D)=Sof(H16E)=Sof(H16F)=Sof(C17A)=
 Sof(H17D)=Sof(H17E)=Sof(H17F)=1-FVAR(1)
 Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(C17)=Sof(H17A)=
 Sof(H17B)=Sof(H17C)=FVAR(1)
 Sof(C30A)=Sof(H30A)=Sof(C31A)=Sof(H31D)=Sof(H31E)=Sof(H31F)=Sof(C32A)=
 Sof(H32D)=Sof(H32E)=Sof(H32F)=1-FVAR(2)
 Sof(C30)=Sof(H30)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)=Sof(C32)=Sof(H32A)=
 Sof(H32B)=Sof(H32C)=FVAR(2)
 Sof(C33A)=Sof(H33A)=Sof(C34A)=Sof(H34D)=Sof(H34E)=Sof(H34F)=Sof(C35A)=
 Sof(H35D)=Sof(H35E)=Sof(H35F)=1-FVAR(3)
 Sof(C33)=Sof(H33)=Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(H34C)=Sof(C35)=Sof(H35A)=
 Sof(H35B)=Sof(H35C)=FVAR(3)
5.a Ternary CH refined with riding coordinates:
 C15(H15), C12(H12), C18(H18), C30(H30), C33(H33), C27(H27), C15A(H15A),
 C30A(H30A), C33A(H33A)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C8(H8), C10(H10), C23(H23), C25(H25)
5.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C31(H31A,H31B,H31C), C32(H32A,
 H32B,H32C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C28(H28A,H28B,H28C),
 C29(H29A,H29B,H29C), C16A(H16D,H16E,H16F), C17A(H17D,H17E,H17F), C31A(H31D,
 H31E,H31F), C32A(H32D,H32E,H32F), C34A(H34D,H34E,H34F), C35A(H35D,H35E,H35F)
;
_shelx_res_checksum              77047
_shelx_hkl_checksum              33124
_olex2_submission_special_instructions 'No special instructions were received'