#------------------------------------------------------------------------------
#$Date: 2016-03-21 09:30:05 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178624 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/35/4073599.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_4073599
loop_
_publ_author_name
'Iglesias, Manuel'
'Beetstra, Dirk J.'
'Stasch, Andreas'
'Horton, Peter N.'
'Hursthouse, Michael B.'
'Coles, Simon J.'
'Cavell, Kingsley J.'
'Dervisi, Athanasia'
'Fallis, Ian A.'
_publ_section_title
;
 First Examples of Diazepanylidene Carbenes and Their
 Late-Transition-Metal Complexes
;
_journal_issue                   19
_journal_name_full               Organometallics
_journal_page_first              4800
_journal_paper_doi               10.1021/om7004904
_journal_volume                  26
_journal_year                    2007
_chemical_formula_sum            'C19 H30 Cl Ir N2 O2'
_chemical_formula_weight         546.10
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 91.532(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   9.274(5)
_cell_length_b                   16.763(5)
_cell_length_c                   13.187(5)
_cell_measurement_temperature    150(2)
_cell_volume                     2049.3(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8708
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         3.28
_exptl_absorpt_coefficient_mu    6.660
_exptl_absorpt_correction_T_max  0.279
_exptl_absorpt_correction_T_min  0.148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sortav (Blessing, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.770
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.768
_refine_diff_density_min         -0.878
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       0.0038(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0228
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0222P)²+2.9581P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0564
_refine_ls_wR_factor_ref         0.0571
_reflns_number_gt                4248
_reflns_number_total             4447
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om7004904-file002.cif
_cod_data_source_block           Ir(CO)2(3)Cl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multi scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4073599
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Ir1 Ir 0.292981(11) 0.032013(6) 0.720651(8) 0.01717(7) Uani 1 1 d .
Cl1 Cl 0.20485(9) 0.11717(5) 0.84785(7) 0.03294(19) Uani 1 1 d .
O1 O 0.1573(3) -0.11278(15) 0.8161(2) 0.0355(6) Uani 1 1 d .
N1 N 0.3401(3) 0.18286(15) 0.60099(19) 0.0201(5) Uani 1 1 d .
C1 C 0.4015(3) 0.13517(17) 0.6706(2) 0.0175(6) Uani 1 1 d .
O2 O 0.3935(3) -0.06366(19) 0.5505(2) 0.0469(7) Uani 1 1 d .
N2 N 0.5294(3) 0.15396(15) 0.71452(19) 0.0204(5) Uani 1 1 d .
C2 C 0.4198(4) 0.24705(19) 0.5505(2) 0.0264(7) Uani 1 1 d .
H2A H 0.3707 0.2599 0.4850 0.032 Uiso 1 1 calc R
H2B H 0.5182 0.2280 0.5360 0.032 Uiso 1 1 calc R
C3 C 0.4307(4) 0.3224(2) 0.6148(3) 0.0314(8) Uani 1 1 d .
H3A H 0.3360 0.3496 0.6151 0.038 Uiso 1 1 calc R
H3B H 0.5018 0.3594 0.5857 0.038 Uiso 1 1 calc R
C4 C 0.4776(4) 0.30022(19) 0.7231(3) 0.0303(7) Uani 1 1 d .
H4A H 0.5168 0.3481 0.7581 0.036 Uiso 1 1 calc R
H4B H 0.3926 0.2817 0.7604 0.036 Uiso 1 1 calc R
C5 C 0.5908(4) 0.23543(18) 0.7245(3) 0.0279(7) Uani 1 1 d .
H5A H 0.6573 0.2448 0.6683 0.033 Uiso 1 1 calc R
H5B H 0.6477 0.2388 0.7889 0.033 Uiso 1 1 calc R
C6 C 0.1903(3) 0.16827(18) 0.5633(2) 0.0216(6) Uani 1 1 d .
H6 H 0.1481 0.1268 0.6082 0.026 Uiso 1 1 calc R
C7 C 0.0973(4) 0.2428(2) 0.5720(2) 0.0259(7) Uani 1 1 d .
H7A H 0.1389 0.2864 0.5314 0.031 Uiso 1 1 calc R
H7B H 0.0966 0.2604 0.6437 0.031 Uiso 1 1 calc R
C8 C -0.0583(4) 0.2261(2) 0.5341(3) 0.0302(7) Uani 1 1 d .
H8A H -0.1036 0.1871 0.5798 0.036 Uiso 1 1 calc R
H8B H -0.1151 0.2760 0.5360 0.036 Uiso 1 1 calc R
C9 C -0.0616(4) 0.1934(2) 0.4265(3) 0.0334(8) Uani 1 1 d .
H9A H -0.0241 0.2340 0.3796 0.040 Uiso 1 1 calc R
H9B H -0.1622 0.1809 0.4052 0.040 Uiso 1 1 calc R
C10 C 0.0302(4) 0.1182(2) 0.4213(3) 0.0419(10) Uani 1 1 d .
H10A H 0.0286 0.0979 0.3507 0.050 Uiso 1 1 calc R
H10B H -0.0111 0.0765 0.4651 0.050 Uiso 1 1 calc R
C11 C 0.1861(4) 0.1347(2) 0.4558(3) 0.0343(8) Uani 1 1 d .
H11A H 0.2426 0.0847 0.4539 0.041 Uiso 1 1 calc R
H11B H 0.2301 0.1734 0.4091 0.041 Uiso 1 1 calc R
C12 C 0.6086(3) 0.09281(18) 0.7749(2) 0.0196(6) Uani 1 1 d .
H12 H 0.5586 0.0409 0.7614 0.024 Uiso 1 1 calc R
C13 C 0.6049(3) 0.10658(19) 0.8891(2) 0.0225(6) Uani 1 1 d .
H13A H 0.5037 0.1118 0.9101 0.027 Uiso 1 1 calc R
H13B H 0.6563 0.1567 0.9067 0.027 Uiso 1 1 calc R
C14 C 0.6767(4) 0.03658(19) 0.9447(3) 0.0265(7) Uani 1 1 d .
H14A H 0.6768 0.0466 1.0187 0.032 Uiso 1 1 calc R
H14B H 0.6205 -0.0126 0.9309 0.032 Uiso 1 1 calc R
C15 C 0.8309(4) 0.0247(2) 0.9112(3) 0.0330(8) Uani 1 1 d .
H15A H 0.8724 -0.0230 0.9452 0.040 Uiso 1 1 calc R
H15B H 0.8898 0.0715 0.9321 0.040 Uiso 1 1 calc R
C16 C 0.8369(4) 0.0143(2) 0.7966(3) 0.0339(8) Uani 1 1 d .
H16A H 0.9389 0.0108 0.7768 0.041 Uiso 1 1 calc R
H16B H 0.7889 -0.0364 0.7770 0.041 Uiso 1 1 calc R
C17 C 0.7641(4) 0.0828(2) 0.7397(3) 0.0285(7) Uani 1 1 d .
H17A H 0.7635 0.0719 0.6659 0.034 Uiso 1 1 calc R
H17B H 0.8187 0.1327 0.7524 0.034 Uiso 1 1 calc R
C18 C 0.2040(3) -0.0579(2) 0.7793(2) 0.0252(7) Uani 1 1 d .
C19 C 0.3610(4) -0.02911(19) 0.6111(3) 0.0301(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'
Cl Cl 0.1484 0.1585 '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
C19 Ir1 C18 92.22(14)
C19 Ir1 C1 91.91(13)
C18 Ir1 C1 173.94(12)
C19 Ir1 Cl1 175.23(10)
C18 Ir1 Cl1 91.61(11)
C1 Ir1 Cl1 84.50(8)
C1 N1 C2 122.6(3)
C1 N1 C6 120.7(2)
C2 N1 C6 116.5(2)
N1 C1 N2 120.8(3)
N1 C1 Ir1 120.5(2)
N2 C1 Ir1 118.6(2)
C1 N2 C12 119.3(2)
C1 N2 C5 125.9(3)
C12 N2 C5 113.9(2)
N1 C2 C3 112.4(3)
C2 C3 C4 109.4(3)
C5 C4 C3 111.5(3)
N2 C5 C4 113.3(3)
N1 C6 C7 111.5(2)
N1 C6 C11 111.9(3)
C7 C6 C11 111.8(3)
C6 C7 C8 110.7(3)
C9 C8 C7 111.3(3)
C8 C9 C10 110.1(3)
C9 C10 C11 111.2(3)
C6 C11 C10 110.1(3)
N2 C12 C13 113.7(2)
N2 C12 C17 111.7(3)
C13 C12 C17 111.2(2)
C12 C13 C14 109.7(3)
C15 C14 C13 111.2(3)
C14 C15 C16 111.2(3)
C17 C16 C15 112.0(3)
C16 C17 C12 110.0(3)
O1 C18 Ir1 176.7(3)
O2 C19 Ir1 177.4(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ir1 C19 1.893(5)
Ir1 C18 1.893(4)
Ir1 C1 2.115(3)
Ir1 Cl1 2.3649(10)
O1 C18 1.132(4)
N1 C1 1.333(4)
N1 C2 1.474(4)
N1 C6 1.483(4)
C1 N2 1.344(4)
O2 C19 1.038(5)
N2 C12 1.481(4)
N2 C5 1.484(4)
C2 C3 1.522(5)
C3 C4 1.528(5)
C4 C5 1.510(5)
C6 C7 1.524(4)
C6 C11 1.525(4)
C7 C8 1.540(5)
C8 C9 1.521(5)
C9 C10 1.523(5)
C10 C11 1.529(5)
C12 C13 1.524(4)
C12 C17 1.536(4)
C13 C14 1.527(4)
C14 C15 1.521(5)
C15 C16 1.524(6)
C16 C17 1.520(5)
