Highly cis-selective cyclopropanations with ethyl diazoacetate using a novel Rh(I) catalyst with a chelating N-heterocyclic iminocarbene ligand.
Rosenberg, Marianne Lenes; Krivokapic, Alexander; Tilset, Mats; Organic letters 11 (2009) 547–550; doi:10.1021/ol802591j

data_1503753
_publ_section_title
;
 Highly cis-selective cyclopropanations with ethyl diazoacetate using a
 novel Rh(I) catalyst with a chelating N-heterocyclic iminocarbene ligand.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              547
_journal_page_last               550
_journal_paper_doi               10.1021/ol802591j
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C20 H19 Cl1 N3 O1 Rh1'
_chemical_formula_sum            'C20 H19 Cl N3 O Rh'
_chemical_formula_weight         455.75
_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   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 93.3020(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3952(10)
_cell_length_b                   10.8758(11)
_cell_length_c                   16.4618(16)
_cell_measurement_reflns_used    4827
_cell_measurement_temperature    103
_cell_measurement_theta_max      28
_cell_measurement_theta_min      2
_cell_volume                     1858.0(3)
_computing_cell_refinement       'SAINT (Siemens ,1995)'
_computing_data_collection       'SMART (Siemens, 1993)'
_computing_data_reduction        'SAINT (Siemens ,1995)'
_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    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      103
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_device       'Bruker SMART'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       '\w '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15730
_diffrn_reflns_theta_full        26.846
_diffrn_reflns_theta_max         28.559
_diffrn_reflns_theta_min         2.246
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.077
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.72
_refine_diff_density_min         -0.63
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0973
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3051
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0282
_refine_ls_shift/su_max          0.001073
_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: 
 1.11 -0.123 0.766 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0363
_refine_ls_wR_factor_gt          0.0311
_refine_ls_wR_factor_ref         0.0296
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                3334
_reflns_number_total             4405
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.46
_oxford_diffrn_Wilson_scale      6.30
_oxford_refine_ls_r_factor_ref   0.0256
_oxford_refine_ls_scale          0.4098(5)
_oxford_reflns_number_all        4392
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            ol802591j_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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_original_formula_sum        'C20 H19 Cl1 N3 O1 Rh1'
_cod_database_code               1503753