Cyclopropenation of internal alkynylsilanes and diazoacetates catalyzed by copper(i) N-heterocyclic carbene complexes.
Thomas, Thomas J.; Merritt, Benjamin A.; Lemma, Betsegaw E.; McKoy, Adina M.; Nguyen, Tri; Swenson, Andrew K.; Mills, Jeffrey L.; Coleman, Michael G.; Organic & biomolecular chemistry 14 (2016) 1742–1747; doi:10.1039/c5ob02259b

data_7154879
_publ_section_title
;
 Cyclopropenation of internal alkynylsilanes and diazoacetates catalyzed
 by copper(i) N-heterocyclic carbene complexes.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1742
_journal_page_last               1747
_journal_paper_doi               10.1039/c5ob02259b
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C20 H21 Cl O2 Si'
_chemical_formula_sum            'C20 H21 Cl O2 Si'
_chemical_formula_weight         356.91
_chemical_melting_point          371(3)
_chemical_name_common            ritmc11
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-11-02 deposited with the CCDC.
2015-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                108.891(3)
_cell_angle_beta                 91.301(3)
_cell_angle_gamma                95.799(3)
_cell_formula_units_Z            2
_cell_length_a                   8.9739(13)
_cell_length_b                   9.8320(14)
_cell_length_c                   11.4770(16)
_cell_measurement_reflns_used    4013
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      38.53
_cell_measurement_theta_min      2.87
_cell_volume                     951.5(2)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014b)'
_computing_structure_solution    'SIR2011 (Burla et al., 2012)'
_diffrn_ambient_temperature      100.0(5)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD platform'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            35515
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        37.785
_diffrn_reflns_theta_max         38.589
_diffrn_reflns_theta_min         1.879
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  0.7476
_exptl_absorpt_correction_T_min  0.6483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014a)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane'
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         10249
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0514P)^2^+0.1796P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0985
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8669
_reflns_number_total             10249
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob02259b2.cif
_cod_data_source_block           ritmc11
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '368.15 - 373.15' was changed to
'371(3)' - the average value was taken and precision was estimated.

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

 Adding full bibliography for 7154879.cif.
;
_cod_database_code               7154879
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.887
_shelx_estimated_absorpt_t_max   0.911
_shelx_res_checksum              84290