Forming N-Heterocyclic Carbene Monolayers: Not All Deposition Methods are the Same
Chandran, Aruna; Dominique, Nathaniel; Kaur, Gurkiran; Clark, Vincent; Nalaoh, Phattananawee; Aloisio, Mark D.; Ekowo, Lilian Chinenye; Jensen , Isabel M; Crudden, Cathleen; Arroyo-Currás, Netzahualcóyotl; Jenkins, David; Camden, Jon; Nanoscale  (2025) –; doi:10.1039/D4NR04428B

data_1573778
_publ_section_title
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 Forming N-Heterocyclic Carbene Monolayers: Not All Deposition Methods are
 the Same
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_journal_name_full               Nanoscale
_journal_paper_doi               10.1039/D4NR04428B
_journal_year                    2025
_chemical_formula_moiety         'C13 H19 N2, C H O3, 7(H2 O)'
_chemical_formula_sum            'C14 H34 N2 O10'
_chemical_formula_weight         390.43
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-06-13
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-08-27 deposited with the CCDC.	2025-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                63.784(2)
_cell_angle_beta                 86.101(2)
_cell_angle_gamma                85.115(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0865(4)
_cell_length_b                   11.5014(5)
_cell_length_c                   12.6813(7)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      70.12
_cell_measurement_theta_min      3.89
_cell_volume                     1053.66(9)
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16270
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.312
_diffrn_reflns_theta_min         3.888
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.886
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1044 before and 0.0523 after correction.
The Ratio of minimum to maximum transmission is 0.8419.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.534
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0197P)^2^+0.9753P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1018
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3561
_reflns_number_total             3838
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nr04428b2.cif
_cod_data_source_block           pn3293_a
_cod_database_code               1573778
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.649
_olex2_refinement_description
;
1. Others
 Fixed Sof: H8B(0.5) H9AA(0.5) H9AB(0.5) H10B(0.5) H8C(0.5) H4B(0.5) H4C(0.5)
 H9BC(0.5) H10C(0.5) H6B(0.5) H6C(0.5) H9BD(0.5)
2.a Free rotating group:
 O4(H4A), O5(H5A,H5B), O6(H6A), O7(H7A,H7B), O8(H8B,H8A), O9(H9AA,H9AB),
 O10(H10B,H10A)
2.b Ternary CH refined with riding coordinates:
 C8(H8), C10(H10)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              87903
_shelx_hkl_checksum              61255
_olex2_submission_special_instructions 'No special instructions were received'