Eight-membered-ring diaminocarbenes bearing naphthalene moiety in the backbone: DFT studies, synthesis of amidinium salts, generation of free carbene, metal complexes, and solvent-free copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction.
Chesnokov, Gleb A.; Topchiy, Maxim A.; Dzhevakov, Pavel B.; Gribanov, Pavel S.; Tukov, Aleksandr A.; Khrustalev, Victor N.; Asachenko, Andrey F.; Nechaev, Mikhail S.; Dalton transactions (Cambridge, England : 2003) 46 (2017) 4331–4345; doi:10.1039/c6dt04484k

data_7042013
_publ_section_title
;
 Eight-membered-ring diaminocarbenes bearing naphthalene moiety in the
 backbone: DFT studies, synthesis of amidinium salts, generation of free
 carbene, metal complexes, and solvent-free copper catalyzed azide-alkyne
 cycloaddition (CuAAC) reaction.
;
_journal_issue                   13
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4331
_journal_page_last               4345
_journal_paper_doi               10.1039/c6dt04484k
_journal_volume                  46
_journal_year                    2017
_chemical_formula_moiety         'C37 H44 Br Cu N2'
_chemical_formula_sum            'C37 H44 Br Cu N2'
_chemical_formula_weight         660.19
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2016-03-07 deposited with the CCDC.
2017-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.137(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0973(11)
_cell_length_b                   19.2875(19)
_cell_length_c                   16.1494(16)
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_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      21.62
_cell_measurement_theta_min      2.30
_cell_volume                     3379.3(6)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_unetI/netI     0.1032
_diffrn_reflns_Laue_measured_fraction_full 1.000
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_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            43668
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_diffrn_reflns_theta_max         30.497
_diffrn_reflns_theta_min         1.667
_diffrn_source                   'fine-focus sealed tube'
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_exptl_absorpt_correction_T_max  0.696
_exptl_absorpt_correction_T_min  0.636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2003)'
_exptl_crystal_colour            colourless
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_exptl_crystal_description       prism
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_exptl_crystal_size_mid          0.20
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_refine_diff_density_max         0.648
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_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
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_refine_ls_number_reflns         10273
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.1345
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_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^)+(0.0554P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1416
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5351
_reflns_number_total             10273
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6dt04484k2.cif
_cod_data_source_block           8_CuBr
_cod_depositor_comments
'Adding full bibliography for 7042011--7042013.cif.'
_cod_database_code               7042013
_shelx_estimated_absorpt_t_min   0.654
_shelx_estimated_absorpt_t_max   0.708
_shelxl_version_number           2014/6
_shelx_res_checksum              10716