Trapping Carbon Suboxide with a Carbene and Isolation of the Carbene-stabilized Carbon Suboxide Dimer
George, Tanner; Johnson, Erin R.; Masuda, Jason Douglas; Chemical Science  (2025) –; doi:10.1039/D5SC06444A

data_1576001
_publ_section_title
;
 Trapping Carbon Suboxide with a Carbene and Isolation of the
 Carbene-stabilized Carbon Suboxide Dimer
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC06444A
_journal_year                    2025
_chemical_formula_moiety         'C30 H40 N2 O3, C2 H6 O'
_chemical_formula_sum            'C32 H46 N2 O4'
_chemical_formula_weight         522.71
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-03-30
_audit_creation_method
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_audit_update_record
;
2025-03-31 deposited with the CCDC.	2025-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.5820(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3172(3)
_cell_length_b                   15.9926(4)
_cell_length_c                   19.0057(6)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.44
_cell_measurement_theta_min      2.35
_cell_volume                     3129.79(16)
_computing_cell_refinement       'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_data_collection       'APEX4 (Bruker AXS Inc., 2021)'
_computing_data_reduction        'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '\k--geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            108293
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.147
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1259 before and 0.0691 after correction.
The Ratio of minimum to maximum transmission is 0.8288.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.109
_exptl_crystal_description       plate
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         6386
_refine_ls_number_restraints     85
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0695
_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^)+(0.1180P)^2^+1.9836P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1836
_refine_ls_wR_factor_ref         0.2526
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4114
_reflns_number_total             6386
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc06444a2.cif
_cod_data_source_block           mo_2022_11_17_jdm_tg403etoh_0m_a
_cod_database_code               1576001
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.981
_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, All O(H) groups
2. Restrained distances
 O4A-C32A
 2.36 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
O4A \\sim C31A \\sim C32A \\sim O4B \\sim C31B \\sim C32B: within 2A with sigma
of 0.001 and sigma for terminal atoms of 0.002 within 2A
4. Rigid body (RIGU) restrains
 O4A, C31A, C32A, O4B, C31B, C32B
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: O4B(0.5) H4B(0.5) C31B(0.5) H31A(0.5) H31B(0.5) C32B(0.5)
 H32A(0.5) H32B(0.5) H32C(0.5) O4A(0.5) H4A(0.5) C31A(0.5) H31C(0.5) H31D(0.5)
 C32A(0.5) H32D(0.5) H32E(0.5) H32F(0.5)
6.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C22(H22), C25(H25)
6.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C31B(H31A,H31B), C31A(H31C,H31D)
6.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20), C29(H29)
6.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C), C32B(H32A,H32B,H32C), C32A(H32D,H32E,H32F)
6.e Idealised tetrahedral OH refined as rotating group:
 O4B(H4B), O4A(H4A)
;
_shelx_res_checksum              55020
_olex2_submission_special_instructions 'No special instructions were received'