#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:25:54 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178715 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/26/4082693.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_4082693
loop_
_publ_author_name
'Teo, Jing Wei'
'Sridevi, Venugopal Shanmugham'
'Leong, Weng Kee'
_publ_section_title
;
 N-Metallacycles from [Cp*MX2]2and Alkynylpyridines: Synthesis, Reaction
 Pathway, and Aromaticity
;
_journal_issue                   5
_journal_name_full               Organometallics
_journal_page_first              1174
_journal_paper_doi               10.1021/om401154c
_journal_volume                  33
_journal_year                    2014
_chemical_formula_sum            'C17 H20 Cl2 Ir N'
_chemical_formula_weight         501.44
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.71(3)
_cell_angle_beta                 74.99(3)
_cell_angle_gamma                64.67(3)
_cell_formula_units_Z            2
_cell_length_a                   8.1568(16)
_cell_length_b                   8.2765(17)
_cell_length_c                   14.305(3)
_cell_measurement_reflns_used    4312
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      28.89
_cell_measurement_theta_min      2.70
_cell_volume                     837.3(4)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_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  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            23565
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    8.284
_exptl_absorpt_correction_T_max  0.6363
_exptl_absorpt_correction_T_min  0.1449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.989
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.676
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3420
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0231
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0168P)²+1.6104P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0538
_refine_ls_wR_factor_ref         0.0543
_reflns_number_gt                3305
_reflns_number_total             3420
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om401154c_si_002.cif
_cod_data_source_block           sd34one
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        837.4(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4082693
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Ir1 Ir 0.38157(2) 0.17688(2) 0.214084(12) 0.03556(6) Uani 1 1 d .
Cl1 Cl 0.17386(15) 0.06160(17) 0.18880(9) 0.0482(3) Uani 1 1 d .
Cl2 Cl 0.6499(2) -0.34570(17) 0.40581(11) 0.0655(4) Uani 1 1 d .
N1 N 0.2672(5) 0.1401(5) 0.3606(3) 0.0400(8) Uani 1 1 d .
C1 C 0.1080(7) 0.2571(7) 0.4040(4) 0.0525(12) Uani 1 1 d U
H1 H 0.0440 0.3642 0.3673 0.063 Uiso 1 1 calc R
C2 C 0.0332(8) 0.2265(9) 0.5015(4) 0.0640(14) Uani 1 1 d U
H2 H -0.0791 0.3119 0.5304 0.077 Uiso 1 1 calc R
C3 C 0.1235(8) 0.0733(9) 0.5537(4) 0.0640(15) Uani 1 1 d U
H3 H 0.0761 0.0516 0.6203 0.077 Uiso 1 1 calc R
C4 C 0.2882(8) -0.0543(8) 0.5095(4) 0.0598(13) Uani 1 1 d U
H4 H 0.3514 -0.1627 0.5457 0.072 Uiso 1 1 calc R
C5 C 0.3581(6) -0.0193(6) 0.4110(3) 0.0404(9) Uani 1 1 d U
C6 C 0.5189(6) -0.1335(6) 0.3500(3) 0.0408(10) Uani 1 1 d U
C7 C 0.5557(6) -0.0761(6) 0.2573(3) 0.0392(9) Uani 1 1 d U
H7 H 0.6559 -0.1472 0.2137 0.047 Uiso 1 1 calc R
C8 C 0.5378(6) 0.3395(6) 0.1874(4) 0.0474(11) Uani 1 1 d U
C9 C 0.5813(6) 0.2510(6) 0.1033(3) 0.0418(10) Uani 1 1 d U
C10 C 0.4175(6) 0.3097(7) 0.0663(4) 0.0491(11) Uani 1 1 d U
C11 C 0.2696(7) 0.4438(7) 0.1256(5) 0.0606(15) Uani 1 1 d U
C12 C 0.3453(7) 0.4619(6) 0.1982(4) 0.0579(14) Uani 1 1 d U
C13 C 0.6731(8) 0.3326(8) 0.2436(4) 0.0633(14) Uani 1 1 d U
H13A H 0.7241 0.4216 0.2124 0.095 Uiso 1 1 calc R
H13B H 0.7720 0.2137 0.2451 0.095 Uiso 1 1 calc R
H13C H 0.6106 0.3582 0.3097 0.095 Uiso 1 1 calc R
C14 C 0.7694(6) 0.1232(7) 0.0609(4) 0.0532(12) Uani 1 1 d U
H14A H 0.7574 0.0459 0.0230 0.080 Uiso 1 1 calc R
H14B H 0.8341 0.0501 0.1131 0.080 Uiso 1 1 calc R
H14C H 0.8385 0.1908 0.0191 0.080 Uiso 1 1 calc R
C15 C 0.3962(8) 0.2595(9) -0.0222(4) 0.0671(16) Uani 1 1 d U
H15A H 0.3760 0.3614 -0.0725 0.101 Uiso 1 1 calc R
H15B H 0.2914 0.2255 -0.0065 0.101 Uiso 1 1 calc R
H15C H 0.5074 0.1590 -0.0454 0.101 Uiso 1 1 calc R
C16 C 0.0727(8) 0.5384(9) 0.1105(6) 0.091(2) Uani 1 1 d U
H16A H 0.0221 0.4499 0.1141 0.136 Uiso 1 1 calc R
H16B H 0.0695 0.6089 0.0469 0.136 Uiso 1 1 calc R
H16C H -0.0001 0.6173 0.1606 0.136 Uiso 1 1 calc R
C17 C 0.2509(10) 0.5877(8) 0.2754(6) 0.086(2) Uani 1 1 d U
H17A H 0.2920 0.5266 0.3361 0.130 Uiso 1 1 calc R
H17B H 0.1182 0.6252 0.2848 0.130 Uiso 1 1 calc R
H17C H 0.2816 0.6926 0.2552 0.130 Uiso 1 1 calc R
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'
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
C7 Ir1 N1 77.62(17)
C7 Ir1 C8 105.41(18)
N1 Ir1 C8 112.38(17)
C7 Ir1 C9 97.49(17)
N1 Ir1 C9 149.09(17)
C8 Ir1 C9 38.86(18)
C7 Ir1 C10 123.31(19)
N1 Ir1 C10 159.07(17)
C8 Ir1 C10 64.5(2)
C9 Ir1 C10 38.15(17)
C7 Ir1 C12 141.3(2)
N1 Ir1 C12 100.75(18)
C8 Ir1 C12 38.76(18)
C9 Ir1 C12 64.04(18)
C10 Ir1 C12 63.2(2)
C7 Ir1 C11 160.96(19)
N1 Ir1 C11 120.54(19)
C8 Ir1 C11 63.9(2)
C9 Ir1 C11 64.11(17)
C10 Ir1 C11 38.6(2)
C12 Ir1 C11 36.7(2)
C7 Ir1 Cl1 90.74(12)
N1 Ir1 Cl1 84.49(11)
C8 Ir1 Cl1 158.54(14)
C9 Ir1 Cl1 126.33(13)
C10 Ir1 Cl1 94.97(14)
C12 Ir1 Cl1 127.86(16)
C11 Ir1 Cl1 96.46(16)
C1 N1 C5 119.9(4)
C1 N1 Ir1 123.8(3)
C5 N1 Ir1 116.2(3)
N1 C1 C2 122.4(5)
C3 C2 C1 118.9(5)
C2 C3 C4 120.0(5)
C5 C4 C3 119.3(5)
N1 C5 C4 119.4(4)
N1 C5 C6 111.8(4)
C4 C5 C6 128.8(5)
C7 C6 C5 118.7(4)
C7 C6 Cl2 124.5(4)
C5 C6 Cl2 116.8(3)
C6 C7 Ir1 115.6(3)
C9 C8 C12 107.4(5)
C9 C8 C13 126.3(4)
C12 C8 C13 125.5(5)
C9 C8 Ir1 71.2(3)
C12 C8 Ir1 73.5(3)
C13 C8 Ir1 128.9(4)
C10 C9 C8 108.0(4)
C10 C9 C14 126.6(5)
C8 C9 C14 125.4(4)
C10 C9 Ir1 71.7(3)
C8 C9 Ir1 70.0(2)
C14 C9 Ir1 125.4(3)
C9 C10 C11 108.4(5)
C9 C10 C15 127.5(5)
C11 C10 C15 123.9(5)
C9 C10 Ir1 70.2(3)
C11 C10 Ir1 73.0(3)
C15 C10 Ir1 126.6(3)
C12 C11 C10 107.1(4)
C12 C11 C16 127.9(6)
C10 C11 C16 125.0(6)
C12 C11 Ir1 70.9(3)
C10 C11 Ir1 68.4(3)
C16 C11 Ir1 124.5(4)
C11 C12 C8 109.0(5)
C11 C12 C17 127.7(5)
C8 C12 C17 123.3(6)
C11 C12 Ir1 72.4(3)
C8 C12 Ir1 67.8(2)
C17 C12 Ir1 126.7(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ir1 C7 2.036(4)
Ir1 N1 2.077(4)
Ir1 C8 2.140(4)
Ir1 C9 2.156(4)
Ir1 C10 2.175(5)
Ir1 C12 2.217(5)
Ir1 C11 2.236(5)
Ir1 Cl1 2.3997(12)
Cl2 C6 1.762(4)
N1 C1 1.332(6)
N1 C5 1.358(6)
C1 C2 1.386(7)
C2 C3 1.339(9)
C3 C4 1.397(8)
C4 C5 1.395(7)
C5 C6 1.440(6)
C6 C7 1.313(6)
C8 C9 1.429(7)
C8 C12 1.448(7)
C8 C13 1.501(7)
C9 C10 1.415(6)
C9 C14 1.498(6)
C10 C11 1.460(8)
C10 C15 1.484(8)
C11 C12 1.400(9)
C11 C16 1.507(8)
C12 C17 1.503(8)
