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_7134471
_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         '0.053(C64 Ga4 N2), 0.105(C), 0.146[C6H14]'
_chemical_formula_sum            'C35 H54.6 Br0.38 Cl0.62 Ga N'
_chemical_formula_weight         611.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-01-21
_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                 92.844(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   32.7341(19)
_cell_length_b                   23.0166(13)
_cell_length_c                   9.2046(6)
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.44
_cell_volume                     6926.5(7)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_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  0.0936
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            53102
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.609
_diffrn_reflns_theta_min         2.438
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.302
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4754
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1591 before and 0.0951 after correction.
The Ratio of minimum to maximum transmission is 0.6376.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_description       block
_exptl_crystal_F_000             2612
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.859
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         7973
_refine_ls_number_restraints     157
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0492
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1567
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5806
_reflns_number_total             7973
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01531f2.cif
_cod_data_source_block           Compound1
_cod_depositor_comments
'Adding full bibliography for 7134471--7134474.cif.'
_cod_original_formula_sum        'C35 H54.60 Br0.38 Cl0.62 Ga N'
_cod_database_code               7134471
_shelx_shelxl_version_number     2019/3
_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. Restrained distances
 C31-C30
 1.5 with sigma of 0.02
 C38-C37 = C37-C36 = C36-C35 = C35-C34 = C34-C33
 1.52 with sigma of 0.02
 C38-C36 = C35-C33
 2.53 with sigma of 0.04
 C37-C35 = C36-C34
 2.54 with sigma of 0.04
 C15-C16 \\sim C15-C16A
 with sigma of 0.02
 C15-C17 \\sim C15-C17A
 with sigma of 0.02
 C38-C37 \\sim C37-C36 \\sim C36-C35 \\sim C35-C34 \\sim C34-C33
 with sigma of 0.02
 C38-C36 \\sim C36-C34 \\sim C37-C35 \\sim C35-C33
 with sigma of 0.04
 C21-C30 \\sim C21-C30A
 with sigma of 0.02
 C30-C31 \\sim C30A-C31A
 with sigma of 0.02
 C30-C32 \\sim C30A-C32A
 with sigma of 0.02
 C21-C31 \\sim C21-C31A
 with sigma of 0.04
 C21-C32 \\sim C21-C32A
 with sigma of 0.04
 C31-C32 \\sim C31A-C32A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C6 \\sim C15 \\sim C16 \\sim C17 \\sim C16A \\sim C17A: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
C21 \\sim C30 \\sim C31 \\sim C32: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
C38 \\sim C37 \\sim C36 \\sim C35 \\sim C34 \\sim C33: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(C30A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4. Rigid body (RIGU) restrains
 C38, C37, C36, C35, C34, C33
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H15A)=Sof(C16A)=Sof(H16D)=Sof(H16E)=Sof(H16F)=Sof(C17A)=Sof(H17D)=
 Sof(H17E)=Sof(H17F)=1-FVAR(1)
 Sof(H15)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(C17)=Sof(H17A)=Sof(H17B)=
 Sof(H17C)=FVAR(1)
 Sof(Br1)=1-FVAR(2)
 Sof(Cl1)=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)
 Fixed Sof: C38(0.5) H38C(0.5) H38A(0.5) H38B(0.5) C37(0.5) H37A(0.5)
 H37B(0.5) C36(0.5) H36A(0.5) H36B(0.5) C35(0.5) H35A(0.5) H35B(0.5) C34(0.5)
 H34A(0.5) H34B(0.5) C33(0.5) H33A(0.5) H33B(0.5) H33C(0.5)
6.a Ternary CH refined with riding coordinates:
 C9(H9), C12(H12), C15(H15), C15(H15A), C24(H24), C28(H28), C30(H30), C30A(H30A)
6.b Secondary CH2 refined with riding coordinates:
 C37(H37A,H37B), C36(H36A,H36B), C35(H35A,H35B), C34(H34A,H34B)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C7(H7), C20(H20), C22(H22)
6.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13C,H13A,H13B), C14(H14A,H14C,
 H14B), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C25(H25A,H25B,H25C), C26(H26A,
 H26B,H26C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C31(H31A,H31B,H31C),
 C32(H32A,H32B,H32C), C16A(H16D,H16E,H16F), C17A(H17D,H17E,H17F), C38(H38C,H38A,
 H38B), C33(H33A,H33B,H33C), C31A(H31D,H31E,H31F), C32A(H32D,H32E,H32F)
;
_shelx_res_checksum              37857
_shelx_hkl_checksum              23455
_olex2_submission_special_instructions 'No special instructions were received'