CuAAC Functionalization of Azide-Tagged Copper(I)-NHCs Acting as Catalyst and Substrate
Gibard, Clémentine; Avignant, Daniel; Cisnetti, Federico; Gautier, Arnaud; Organometallics 31 (2012) 7902–; doi:10.1021/om3005355

data_4079161
_publ_section_title
;
 CuAAC Functionalization of Azide-Tagged Copper(I)-NHCs Acting as Catalyst
 and Substrate
;
_journal_issue                   22
_journal_name_full               Organometallics
_journal_page_first              7902
_journal_paper_doi               10.1021/om3005355
_journal_volume                  31
_journal_year                    2012
_chemical_compound_source        synthetic
_chemical_formula_moiety         'C27 H34 Cl1 Cu1 N8'
_chemical_formula_sum            'C27 H34 Cl Cu N8'
_chemical_formula_weight         569.62
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90.538(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7500(4)
_cell_length_b                   15.3223(7)
_cell_length_c                   22.0934(9)
_cell_measurement_reflns_used    6381
_cell_measurement_temperature    293
_cell_measurement_theta_max      24.50
_cell_measurement_theta_min      2.29
_cell_volume                     3300.4(2)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7645
_diffrn_reflns_theta_full        27.132
_diffrn_reflns_theta_max         27.685
_diffrn_reflns_theta_min         1.617
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.769
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.993
_exptl_crystal_size_mid          0.274
_exptl_crystal_size_min          0.154
_platon_squeeze_details
;
The unit cell contained dichloromethane molecule that have been treated by the SQUEEZE function in the PLATON program (Spek, 2003). 
;
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0680
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         3424
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1106
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0.0006262
_refine_ls_shift/su_mean         0.0000203
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 0.605 0.806 0.491 0.195 0.753E-01 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1443
_refine_ls_wR_factor_gt          0.0552
_refine_ls_wR_factor_ref         0.0529
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              0
_reflns_number_gt                3701
_reflns_number_total             7645
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0497
_oxford_refine_ls_scale          0.1247(3)
_oxford_reflns_number_all        7623
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            om3005355_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_atom_sites_solution_primary' value 'Direct' changed to
'direct' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_original_formula_sum        'C27 H34 Cl1 Cu1 N8'
_cod_database_code               4079161
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  11,X'S) H   ( 113,X'S) H   ( 112,X'S) H   ( 111,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) H   ( 123,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) H   ( 272,X'S) H   ( 273,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) H   ( 233,X'S) 
RIDE C   (  24,X'S) H   ( 243,X'S) H   ( 242,X'S) H   ( 241,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) H   ( 262,X'S) H   ( 263,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) H   ( 142,X'S) H   ( 143,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 152,X'S) H   ( 153,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
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