A bifunctional strategy for N-heterocyclic carbene-stabilized iridium complex-catalyzed N-alkylation of amines with alcohols in aqueous media
Huang, Ming; Li, Yinwu; Liu, Jiahao; Lan, Xiao-Bing; Liu, Yan; Zhao, Cunyuan; Ke, Zhuofeng; Green Chemistry 21 (2019) 219–; doi:10.1039/C8GC02298D

data_7231992
_publ_section_title
;
 A bifunctional strategy for N-heterocyclic carbene-stabilized iridium
 complex-catalyzed N-alkylation of amines with alcohols in aqueous media
;
_journal_issue                   2
_journal_name_full               'Green Chemistry'
_journal_page_first              219
_journal_paper_doi               10.1039/C8GC02298D
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C20 H26 Cl Ir N3 O, F6 P'
_chemical_formula_sum            'C20 H26 Cl F6 Ir N3 O P'
_chemical_formula_weight         697.06
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-03-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-03-12 deposited with the CCDC.
2018-12-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5409(7)
_cell_length_b                   12.9814(8)
_cell_length_c                   13.6168(8)
_cell_measurement_reflns_used    2905
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23
_cell_measurement_theta_min      2
_cell_volume                     2393.6(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0898
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            30879
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.677
_diffrn_reflns_theta_min         2.992
_exptl_absorpt_coefficient_mu    5.821
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.934
_exptl_crystal_description       block
_exptl_crystal_F_000             1352
_refine_diff_density_max         0.830
_refine_diff_density_min         -2.260
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2380
_refine_ls_number_restraints     83
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0543P)^2^+6.8434P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1115
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2001
_reflns_number_total             2380
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8gc02298d2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7231992.cif.'
_cod_database_code               7231992
_shelx_shelxl_version_number     2014/7
_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, All O(H) groups
2. Restrained distances
 C5-C6 \\sim C6-N2
 with sigma of 0.02
3. Rigid bond restraints
 C10, C9, N2, C7, C8, N3, C6
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F2, F3, F4, F1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C10 \\sim C9 \\sim N2 \\sim C7 \\sim C8 \\sim N3 \\sim C6: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08
F3 \\sim F4 \\sim F1 \\sim F2: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08
Uanis(F2) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F1) \\sim
Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
5. Others
 Fixed Sof: Cl1(0.5) C6(0.5) H6A(0.5) H6B(0.5) H16A(0.5) H16B(0.5) H16C(0.5)
 C10(0.5) H10A(0.5) H10B(0.5) H10C(0.5) O1(0.5) H1(0.5) C2(0.5) H2(0.5) C3(0.5)
 H3(0.5) C4(0.5) H4(0.5) C5(0.5) N1(0.5) C1(0.5) C9(0.5) N2(0.5) C7(0.5)
 H7(0.5) C8(0.5) H8(0.5) N3(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7), C8(H8)
6.c Fitted pentagon refined as free rotating group:
 C9(N2,C7,C8,N3)
6.d Fitted hexagon refined as free rotating group:
 C2(C3,C4,C5,N1,C1)
6.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C10(H10A,H10B,H10C), C15(H15A,H15B,H15C), C14(H14A,H14B,
 H14C)
6.f Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'