#------------------------------------------------------------------------------
#$Date: 2020-10-06 08:47:13 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257206 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/79/1557984.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1557984
loop_
_publ_author_name
'González-Lainez, Miguel'
'Jiménez, M. Victoria'
'Passarelli, Vincenzo'
'Pérez-Torrente, Jesús J.'
_publ_section_title
;
 Effective N-methylation of nitroarenes with methanol catalyzed by a
 functionalized NHC-based iridium catalyst: a green approach to N-methyl
 amines
;
_journal_issue                   10
_journal_name_full               'Catalysis Science & Technology'
_journal_page_first              3458
_journal_page_last               3467
_journal_paper_doi               10.1039/D0CY00707B
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C17 H21 Br Ir N3 O3'
_chemical_formula_sum            'C17 H21 Br Ir N3 O3'
_chemical_formula_weight         587.48
_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     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-07-23 deposited with the CCDC.	2020-05-01 downloaded from the CCDC.
;
_cell_angle_alpha                99.1570(10)
_cell_angle_beta                 110.946(2)
_cell_angle_gamma                114.3940(10)
_cell_formula_units_Z            2
_cell_length_a                   9.2294(9)
_cell_length_b                   11.1211(11)
_cell_length_c                   11.8920(19)
_cell_measurement_reflns_used    7571
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.267
_cell_measurement_theta_min      2.335
_cell_volume                     968.3(2)
_computing_cell_refinement       'SAINT+ in APEX2 (Bruker AXS,2008)'
_computing_data_collection       'SMART in APEX2 (Bruker AXS,2008)'
_computing_data_reduction        'SAINT+ in APEX2 (Bruker AXS,2008)'
_computing_molecular_graphics    'XP program, SHELXTL v6.12, Bruker2000'
_computing_publication_material  'XCIF program, PLATON(Spek, 1998)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX DUO system'
_diffrn_measurement_method       'ω and φ rotations with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11641
_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         26.368
_diffrn_reflns_theta_min         1.966
_exptl_absorpt_coefficient_mu    8.978
_exptl_absorpt_correction_T_max  0.1695
_exptl_absorpt_correction_T_min  0.1208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 Multi-scan correction included in APEX2 package (Bruker AXS, 2008)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.015
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         2.507
_refine_diff_density_min         -2.000
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3938
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0290
_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/[σ²(Fo²)+(0.0311P)²+5.1495P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0740
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3700
_reflns_number_total             3938
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cy00707b2.cif
_cod_data_source_block           cmpd_4_VPX142
_cod_depositor_comments
;Adding full bibliography for 1557983--1557984.cif.

 Adding full bibliography for 1557983--1557984.cif.
;
_cod_database_code               1557984
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C6A C 0.9120(18) -0.3305(12) 0.6537(12) 0.027(4) Uiso 0.401(16) 1 d D . P A 1
C7A C 0.7091(16) -0.4241(16) 0.6077(15) 0.043(4) Uiso 0.401(16) 1 d D . P A 1
H7A1 H 0.6877 -0.4238 0.6827 0.065 Uiso 0.401(16) 1 calc R U P A 1
H7A2 H 0.6672 -0.5211 0.5568 0.065 Uiso 0.401(16) 1 calc R U P A 1
H7A3 H 0.6431 -0.3870 0.5542 0.065 Uiso 0.401(16) 1 calc R U P A 1
C8A C 0.941(2) -0.319(2) 0.5377(15) 0.056(5) Uiso 0.401(16) 1 d D . P A 1
H8A1 H 0.8675 -0.2842 0.4882 0.085 Uiso 0.401(16) 1 calc R U P A 1
H8A2 H 0.9052 -0.4126 0.4831 0.085 Uiso 0.401(16) 1 calc R U P A 1
H8A3 H 1.0685 -0.2532 0.5666 0.085 Uiso 0.401(16) 1 calc R U P A 1
C9A C 1.0068(16) -0.4016(15) 0.7236(13) 0.025(3) Uiso 0.401(16) 1 d D . P A 1
H9A1 H 1.1314 -0.3561 0.7378 0.037 Uiso 0.401(16) 1 calc R U P A 1
H9A2 H 0.9430 -0.5022 0.6709 0.037 Uiso 0.401(16) 1 calc R U P A 1
H9A3 H 1.0067 -0.3919 0.8070 0.037 Uiso 0.401(16) 1 calc R U P A 1
C6B C 0.8825(14) -0.3404(9) 0.6607(9) 0.029(3) Uiso 0.599(16) 1 d D . P A 2
C7B C 0.7252(14) -0.4319(12) 0.6793(11) 0.047(3) Uiso 0.599(16) 1 d D . P A 2
H7B1 H 0.7656 -0.4160 0.7714 0.071 Uiso 0.599(16) 1 calc R U P A 2
H7B2 H 0.6762 -0.5317 0.6317 0.071 Uiso 0.599(16) 1 calc R U P A 2
H7B3 H 0.6314 -0.4075 0.6471 0.071 Uiso 0.599(16) 1 calc R U P A 2
C8B C 0.8192(15) -0.3536(12) 0.5194(9) 0.044(3) Uiso 0.599(16) 1 d D . P A 2
H8B1 H 0.7191 -0.3354 0.4906 0.067 Uiso 0.599(16) 1 calc R U P A 2
H8B2 H 0.7787 -0.4493 0.4663 0.067 Uiso 0.599(16) 1 calc R U P A 2
H8B3 H 0.9191 -0.2844 0.5107 0.067 Uiso 0.599(16) 1 calc R U P A 2
C9B C 1.0230(17) -0.3869(17) 0.6959(14) 0.061(4) Uiso 0.599(16) 1 d D . P A 2
H9B1 H 1.1180 -0.3320 0.6754 0.092 Uiso 0.599(16) 1 calc R U P A 2
H9B2 H 0.9646 -0.4878 0.6465 0.092 Uiso 0.599(16) 1 calc R U P A 2
H9B3 H 1.0759 -0.3705 0.7884 0.092 Uiso 0.599(16) 1 calc R U P A 2
C1 C 0.8942(7) -0.1078(5) 0.7301(5) 0.0283(10) Uani 1 1 d . . . . .
C4 C 1.1616(8) 0.0113(6) 0.9120(5) 0.0391(13) Uani 1 1 d . . . . .
H4 H 1.2621 0.0843 0.9900 0.047 Uiso 1 1 calc R U . . .
C3 C 1.1375(7) -0.1153(6) 0.8576(5) 0.0359(12) Uani 1 1 d . . . . .
H3 H 1.2177 -0.1487 0.8896 0.043 Uiso 1 1 calc R U . . .
C10 C 0.9825(8) 0.1328(6) 0.8639(6) 0.0362(12) Uani 1 1 d . . . . .
H10A H 0.9813 0.1460 0.9478 0.043 Uiso 1 1 calc R U . . .
H10B H 0.8620 0.1069 0.7973 0.043 Uiso 1 1 calc R U . . .
C11 C 1.1209(7) 0.2711(5) 0.8709(5) 0.0281(10) Uani 1 1 d . . . . .
C13 C 1.2621(7) 0.5126(6) 0.9612(5) 0.0287(11) Uani 1 1 d . . . . .
C14 C 1.3531(7) 0.5316(6) 0.8885(5) 0.0303(11) Uani 1 1 d . . . . .
H14 H 1.4332 0.6239 0.8962 0.036 Uiso 1 1 calc R U . . .
C15 C 1.3240(7) 0.4124(6) 0.8042(5) 0.0313(11) Uani 1 1 d . . . . .
H15 H 1.3844 0.4216 0.7533 0.038 Uiso 1 1 calc R U . . .
C16 C 1.2058(7) 0.2798(6) 0.7953(5) 0.0302(11) Uani 1 1 d . . . . .
H16 H 1.1836 0.1966 0.7383 0.036 Uiso 1 1 calc R U . . .
C17 C 1.2892(8) 0.6352(6) 1.0578(6) 0.0343(12) Uani 1 1 d . . . . .
H17A H 1.1708 0.6208 1.0461 0.041 Uiso 1 1 calc R U . . .
H17B H 1.3580 0.6413 1.1464 0.041 Uiso 1 1 calc R U . . .
C19 C 1.4440(8) 0.8835(6) 1.1441(6) 0.0424(14) Uani 1 1 d . . . . .
H19A H 1.3398 0.8793 1.1515 0.064 Uiso 1 1 calc R U . . .
H19B H 1.5058 0.9692 1.1278 0.064 Uiso 1 1 calc R U . . .
H19C H 1.5273 0.8855 1.2246 0.064 Uiso 1 1 calc R U . . .
C20 C 0.7584(8) -0.0644(7) 0.4958(6) 0.0379(13) Uani 1 1 d . . . . .
C22 C 0.4193(8) -0.1847(6) 0.4701(6) 0.0393(13) Uani 1 1 d . . . . .
N5 N 1.0134(6) 0.0157(5) 0.8336(4) 0.0313(10) Uani 1 1 d D . . . .
N2 N 0.9726(6) -0.1884(5) 0.7452(4) 0.0297(9) Uani 1 1 d . . . . .
N12 N 1.1476(6) 0.3852(5) 0.9535(4) 0.0272(9) Uani 1 1 d . . . . .
O18 O 1.3851(6) 0.7629(4) 1.0408(4) 0.0427(10) Uani 1 1 d . . . . .
O21 O 0.8206(6) -0.0143(5) 0.4424(4) 0.0458(10) Uani 1 1 d . . . . .
O23 O 0.2813(6) -0.2126(5) 0.3963(5) 0.0562(13) Uani 1 1 d . . . . .
Br Br 0.51080(9) -0.23075(7) 0.72700(6) 0.04674(16) Uani 1 1 d . . . . .
Ir Ir 0.64928(3) -0.14476(2) 0.59172(2) 0.02895(8) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8A C6A N2 112.1(11) . . ?
C8A C6A C9A 110.5(10) . . ?
N2 C6A C9A 110.8(9) . . ?
C8A C6A C7A 108.9(10) . . ?
N2 C6A C7A 106.8(10) . . ?
C9A C6A C7A 107.6(9) . . ?
C6A C7A H7A1 109.5 . . ?
C6A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
C6A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
C6A C8A H8A1 109.5 . . ?
C6A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
C6A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
C6A C9A H9A1 109.5 . . ?
C6A C9A H9A2 109.5 . . ?
H9A1 C9A H9A2 109.5 . . ?
C6A C9A H9A3 109.5 . . ?
H9A1 C9A H9A3 109.5 . . ?
H9A2 C9A H9A3 109.5 . . ?
N2 C6B C7B 110.2(8) . . ?
N2 C6B C8B 109.8(7) . . ?
C7B C6B C8B 110.3(8) . . ?
N2 C6B C9B 108.3(9) . . ?
C7B C6B C9B 111.0(8) . . ?
C8B C6B C9B 107.2(8) . . ?
C6B C7B H7B1 109.5 . . ?
C6B C7B H7B2 109.5 . . ?
H7B1 C7B H7B2 109.5 . . ?
C6B C7B H7B3 109.5 . . ?
H7B1 C7B H7B3 109.5 . . ?
H7B2 C7B H7B3 109.5 . . ?
C6B C8B H8B1 109.5 . . ?
C6B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
C6B C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
H8B2 C8B H8B3 109.5 . . ?
C6B C9B H9B1 109.5 . . ?
C6B C9B H9B2 109.5 . . ?
H9B1 C9B H9B2 109.5 . . ?
C6B C9B H9B3 109.5 . . ?
H9B1 C9B H9B3 109.5 . . ?
H9B2 C9B H9B3 109.5 . . ?
N2 C1 N5 104.7(4) . . ?
N2 C1 Ir 132.8(4) . . ?
N5 C1 Ir 122.5(4) . . ?
C3 C4 N5 107.2(5) . . ?
C3 C4 H4 126.4 . . ?
N5 C4 H4 126.4 . . ?
C4 C3 N2 107.1(5) . . ?
C4 C3 H3 126.5 . . ?
N2 C3 H3 126.5 . . ?
N5 C10 C11 114.2(4) . . ?
N5 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
N5 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
N12 C11 C16 123.3(5) . . ?
N12 C11 C10 113.5(4) . . ?
C16 C11 C10 123.1(5) . . ?
N12 C13 C14 123.2(5) . . ?
N12 C13 C17 114.7(5) . . ?
C14 C13 C17 122.1(5) . . ?
C15 C14 C13 118.2(5) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
C16 C15 C14 119.2(5) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C11 C16 C15 118.6(5) . . ?
C11 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
O18 C17 C13 109.7(5) . . ?
O18 C17 H17A 109.7 . . ?
C13 C17 H17A 109.7 . . ?
O18 C17 H17B 109.7 . . ?
C13 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
O18 C19 H19A 109.5 . . ?
O18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O21 C20 Ir 177.5(6) . . ?
O23 C22 Ir 177.9(5) . . ?
C1 N5 C4 110.8(5) . . ?
C1 N5 C10 124.9(5) . . ?
C4 N5 C10 124.1(5) . . ?
C1 N2 C3 110.2(5) . . ?
C1 N2 C6B 124.2(5) . . ?
C3 N2 C6B 125.2(5) . . ?
C1 N2 C6A 128.8(6) . . ?
C3 N2 C6A 120.7(6) . . ?
C13 N12 C11 117.5(4) . . ?
C19 O18 C17 111.7(5) . . ?
C20 Ir C22 92.2(2) . . ?
C20 Ir C1 91.0(2) . . ?
C22 Ir C1 176.8(2) . . ?
C20 Ir Br 175.22(18) . . ?
C22 Ir Br 87.6(2) . . ?
C1 Ir Br 89.21(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C6A C8A 1.510(13) . ?
C6A N2 1.510(12) . ?
C6A C9A 1.529(12) . ?
C6A C7A 1.538(13) . ?
C7A H7A1 0.9800 . ?
C7A H7A2 0.9800 . ?
C7A H7A3 0.9800 . ?
C8A H8A1 0.9800 . ?
C8A H8A2 0.9800 . ?
C8A H8A3 0.9800 . ?
C9A H9A1 0.9800 . ?
C9A H9A2 0.9800 . ?
C9A H9A3 0.9800 . ?
C6B N2 1.503(9) . ?
C6B C7B 1.508(11) . ?
C6B C8B 1.529(11) . ?
C6B C9B 1.535(11) . ?
C7B H7B1 0.9800 . ?
C7B H7B2 0.9800 . ?
C7B H7B3 0.9800 . ?
C8B H8B1 0.9800 . ?
C8B H8B2 0.9800 . ?
C8B H8B3 0.9800 . ?
C9B H9B1 0.9800 . ?
C9B H9B2 0.9800 . ?
C9B H9B3 0.9800 . ?
C1 N2 1.362(7) . ?
C1 N5 1.363(6) . ?
C1 Ir 2.084(5) . ?
C4 C3 1.341(9) . ?
C4 N5 1.379(8) . ?
C4 H4 0.9500 . ?
C3 N2 1.393(7) . ?
C3 H3 0.9500 . ?
C10 N5 1.461(7) . ?
C10 C11 1.505(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N12 1.345(7) . ?
C11 C16 1.377(7) . ?
C13 N12 1.336(7) . ?
C13 C14 1.389(8) . ?
C13 C17 1.502(7) . ?
C14 C15 1.387(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(8) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O18 1.423(7) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C19 O18 1.413(7) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 O21 1.073(8) . ?
C20 Ir 1.875(7) . ?
C22 O23 1.130(7) . ?
C22 Ir 1.901(6) . ?
Br Ir 2.4670(7) . ?
