Development of N-Heterocyclic Carbene‒Copper Complexes for 1,3-Halogen Migration
Schmid, Steven C.; Van Hoveln, Ryan; Rigoli, Jared W.; Schomaker, Jennifer M.; Organometallics 34 (2015) 4164–; doi:10.1021/acs.organomet.5b00629

data_4087822
_publ_section_title
;
 Development of N-Heterocyclic Carbene--Copper Complexes for 1,3-Halogen
 Migration
;
_journal_issue                   16
_journal_name_full               Organometallics
_journal_page_first              4164
_journal_paper_doi               10.1021/acs.organomet.5b00629
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C43 H68 Cl Cu N2, 0.5(C2 H4 Cl2)'
_chemical_formula_sum            'C44 H70 Cl2 Cu N2'
_chemical_formula_weight         761.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-14
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2015.03.31 svn.r3164 for OlexSys, GUI svn.r5023)
;
_cell_angle_alpha                65.84(2)
_cell_angle_beta                 82.773(13)
_cell_angle_gamma                84.096(11)
_cell_formula_units_Z            4
_cell_length_a                   12.008(4)
_cell_length_b                   18.286(7)
_cell_length_c                   21.544(7)
_cell_measurement_reflns_used    9848
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.648
_cell_measurement_theta_min      2.446
_cell_volume                     4275(3)
_computing_cell_refinement       'SAINT+ Ver. 8.34A (Bruker-AXS, 2014)'
_computing_data_collection       'APEX2 Ver. 2014.11-0 (Bruker-AXS, 2014)'
_computing_data_reduction        'SAINT+ Ver. 8.34A (Bruker-AXS, 2014)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015b)'
_computing_structure_solution    'XT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '0.5\% \w and 0.5\% \f scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            59730
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.789
_diffrn_reflns_theta_min         1.040
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_correction_T_min  0.8908
_exptl_absorpt_process_details
'SADABS-2014/5 (Krause et al., 2015) was used for absorption correction.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1644
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     899
_refine_ls_number_reflns         16340
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0418
_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^)+(0.0340P)^2^+2.2900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0920
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11666
_reflns_number_total             16340
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om5b00629_si_005.cif
_cod_data_source_block           schomaker56a
_cod_database_code               4087822
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.912
_olex2_refinement_description
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C10(H10), C17(H17), C30(H30), C37(H37), C10A(H10A), C17A(H17A), C30A(H30A),
 C37A(H37A)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B), C15(H15A,H15B), C18(H18A,
 H18B), C19(H19A,H19B), C21(H21A,H21B), C22(H22A,H22B), C31(H31A,H31B),
 C32(H32A,H32B), C34(H34A,H34B), C35(H35A,H35B), C38(H38A,H38B), C39(H39A,H39B),
  C41(H41A,H41B), C42(H42A,H42B), C11A(H11C,H11D), C12A(H12C,H12D), C14A(H14C,
 H14D), C15A(H15C,H15D), C18A(H18C,H18D), C19A(H19C,H19D), C21A(H21C,H21D),
 C22A(H22C,H22D), C31A(H31C,H31D), C32A(H32C,H32D), C34A(H34C,H34D), C35A(H35C,
 H35D), C38A(H38C,H38D), C39A(H39C,H39D), C41A(H41C,H41D), C42A(H42C,H42D),
 C44(H44A,H44B), C45(H45A,H45B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C26(H26), C27(H27), C28(H28),
 C2A(H2A), C3A(H3A), C6A(H6A), C7A(H7A), C8A(H8A), C26A(H26A), C27A(H27A),
 C28A(H28A)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C16(H16A,H16B,H16C), C20(H20A,H20B,H20C), C23(H23A,H23B,
 H23C), C33(H33A,H33B,H33C), C36(H36A,H36B,H36C), C40(H40A,H40B,H40C), C43(H43A,
 H43B,H43C), C13A(H13D,H13E,H13F), C16A(H16D,H16E,H16F), C20A(H20D,H20E,H20F),
 C23A(H23D,H23E,H23F), C33A(H33D,H33E,H33F), C36A(H36D,H36E,H36F), C40A(H40D,
 H40E,H40F), C43A(H43D,H43E,H43F)
;
_shelx_res_checksum              1776
_shelx_hkl_checksum              17058
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'