Synthesis of Hemilabile Cyclic (Alkyl)(amino)carbenes (CAACs) and Applications in Organometallic Chemistry.
Chu, Jiaxiang; Munz, Dominik; Jazzar, Rodolphe; Melaimi, Mohand; Bertrand, Guy; Journal of the American Chemical Society 138 (2016) 7884–7887; doi:10.1021/jacs.6b05221

data_4125110
_publ_section_title
;
 Synthesis of Hemilabile Cyclic (Alkyl)(amino)carbenes (CAACs) and
 Applications in Organometallic Chemistry.
;
_journal_issue                   25
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7884
_journal_page_last               7887
_journal_paper_doi               10.1021/jacs.6b05221
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C22 H36 Cl Cu N2'
_chemical_formula_sum            'C22 H36 Cl Cu N2'
_chemical_formula_weight         427.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-05-10
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.320(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.4234(3)
_cell_length_b                   16.0108(6)
_cell_length_c                   8.5636(3)
_cell_measurement_reflns_used    3118
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.28
_cell_measurement_theta_min      2.425
_cell_volume                     1132.47(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6287
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.396
_diffrn_reflns_theta_min         2.426
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.090
_exptl_absorpt_correction_T_max  0.0916
_exptl_absorpt_correction_T_min  0.0635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0536 before and 0.0373 after correction.
The Ratio of minimum to maximum transmission is 0.6932.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.297(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3784
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0438P)^2^+0.3179P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0822
_reflns_Friedel_coverage         0.927
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3512
_reflns_number_total             3784
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b05221_si_002.cif
_cod_data_source_block           gb_mm77_0m_b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 4125107--4125110.cif.
;
_cod_database_code               4125110
_shelx_estimated_absorpt_t_max   0.888
_shelx_estimated_absorpt_t_min   0.828
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.703(19) 0.297(19)
2. 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
3.a Ternary CH refined with riding coordinates:
 C15(H15), C18(H18)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C3(H3A,H3B)
3.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C12(H12), C11(H11)
3.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C17(H17A,H17B,H17C), C6(H6A,H6B,H6C), C19(H19A,H19B,
 H19C), C16(H16A,H16B,H16C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              98666
_shelx_hkl_checksum              18116
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'