#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:14:30 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178712 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/23/4082313.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_4082313
loop_
_publ_author_name
'Zhang, Long'
'Li, Hao'
'Weng, Lin-Hong'
'Jin, Guo-Xin'
_publ_section_title
;
 Isomers of Cyclometalated Macrocycles Constructed through Olefinic C--H
 Activation
;
_journal_issue                   2
_journal_name_full               Organometallics
_journal_page_first              587
_journal_paper_doi               10.1021/om4011559
_journal_volume                  33
_journal_year                    2014
_chemical_formula_sum            'C22 H24 Cl Ir N2'
_chemical_formula_weight         544.08
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 98.653(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.547(3)
_cell_length_b                   14.682(6)
_cell_length_c                   17.714(7)
_cell_measurement_reflns_used    784
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.054
_cell_measurement_theta_min      2.326
_cell_volume                     1940.5(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0821
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8588
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.007
_diffrn_reflns_theta_min         1.810
_exptl_absorpt_coefficient_mu    7.026
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.862
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.050
_refine_diff_density_max         1.007
_refine_diff_density_min         -1.052
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.794
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3804
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.794
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[σ²(Fo²)] 
 where P=(Fo²+2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0402
_refine_ls_wR_factor_ref         0.0430
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2730
_reflns_number_total             3804
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om4011559_si_001.cif
_cod_data_source_block           Complex_1c
_cod_database_code               4082313
#BEGIN Tags that were not found in dictionaries:
_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. 
;
_shelx_estimated_absorpt_t_min   0.512
_shelx_estimated_absorpt_t_max   0.720
_shelxl_version_number           2013-2
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Ir1 Ir 0.35128(3) 0.18953(2) 0.76922(2) 0.03168(7) Uani 1 1 d . .
Cl1 Cl 0.06415(17) 0.25776(10) 0.77178(8) 0.0469(4) Uani 1 1 d . .
N1 N 0.2741(5) 0.0909(3) 0.8423(2) 0.0342(11) Uani 1 1 d . .
N2 N 0.2493(7) 0.0324(4) 0.5714(3) 0.0583(15) Uani 1 1 d . .
C1 C 0.2929(8) 0.0960(4) 0.9186(3) 0.0515(17) Uani 1 1 d . .
H1 H 0.3490 0.1472 0.9422 0.062 Uiso 1 1 calc R U
C2 C 0.2351(8) 0.0312(4) 0.9632(3) 0.0521(17) Uani 1 1 d . .
H2 H 0.2516 0.0379 1.0160 0.063 Uiso 1 1 calc R U
C3 C 0.1511(8) -0.0449(4) 0.9293(3) 0.0500(17) Uani 1 1 d . .
H3 H 0.1127 -0.0912 0.9589 0.060 Uiso 1 1 calc R U
C4 C 0.1252(7) -0.0514(4) 0.8513(3) 0.0439(15) Uani 1 1 d . .
H4 H 0.0649 -0.1014 0.8276 0.053 Uiso 1 1 calc R U
C5 C 0.1891(7) 0.0168(4) 0.8071(3) 0.0330(13) Uani 1 1 d . .
C6 C 0.1701(7) 0.0200(4) 0.7260(3) 0.0380(14) Uani 1 1 d . .
H6 H 0.1189 -0.0278 0.6958 0.046 Uiso 1 1 calc R U
C7 C 0.2290(6) 0.0944(4) 0.6957(3) 0.0326(13) Uani 1 1 d . .
C8 C 0.2009(7) 0.1035(4) 0.6113(3) 0.0416(15) Uani 1 1 d . .
C9 C 0.1252(7) 0.1824(5) 0.5778(3) 0.0474(15) Uani 1 1 d . .
H9 H 0.0956 0.2305 0.6077 0.057 Uiso 1 1 calc R U
C10 C 0.0946(8) 0.1882(5) 0.4996(4) 0.0619(18) Uani 1 1 d . .
H10 H 0.0423 0.2400 0.4756 0.074 Uiso 1 1 calc R U
C11 C 0.1429(9) 0.1158(6) 0.4573(4) 0.072(2) Uani 1 1 d . .
H11 H 0.1252 0.1179 0.4043 0.086 Uiso 1 1 calc R U
C12 C 0.2163(9) 0.0421(6) 0.4951(4) 0.073(2) Uani 1 1 d . .
H12 H 0.2468 -0.0063 0.4658 0.087 Uiso 1 1 calc R U
C13 C 0.6366(6) 0.1888(4) 0.8015(3) 0.0371(13) Uani 1 1 d . .
C14 C 0.5956(6) 0.2054(4) 0.7217(3) 0.0375(14) Uani 1 1 d . .
C15 C 0.4942(7) 0.2892(4) 0.7123(3) 0.0416(15) Uani 1 1 d . .
C16 C 0.4912(7) 0.3250(4) 0.7862(3) 0.0399(15) Uani 1 1 d . .
C17 C 0.5775(7) 0.2661(4) 0.8406(3) 0.0349(14) Uani 1 1 d . .
C18 C 0.7470(7) 0.1115(4) 0.8387(3) 0.0538(17) Uani 1 1 d . .
H18A H 0.7598 0.0657 0.8012 0.081 Uiso 1 1 calc R U
H18B H 0.6886 0.0857 0.8782 0.081 Uiso 1 1 calc R U
H18C H 0.8633 0.1337 0.8604 0.081 Uiso 1 1 calc R U
C19 C 0.6572(7) 0.1514(4) 0.6590(3) 0.0545(18) Uani 1 1 d . .
H19A H 0.6850 0.0904 0.6764 0.082 Uiso 1 1 calc R U
H19B H 0.7623 0.1792 0.6446 0.082 Uiso 1 1 calc R U
H19C H 0.5640 0.1499 0.6157 0.082 Uiso 1 1 calc R U
C20 C 0.4334(7) 0.3382(4) 0.6385(3) 0.062(2) Uani 1 1 d . .
H20A H 0.3116 0.3578 0.6370 0.093 Uiso 1 1 calc R U
H20B H 0.4412 0.2980 0.5964 0.093 Uiso 1 1 calc R U
H20C H 0.5086 0.3903 0.6349 0.093 Uiso 1 1 calc R U
C21 C 0.4083(7) 0.4144(4) 0.8004(3) 0.0575(18) Uani 1 1 d . .
H21A H 0.4145 0.4236 0.8544 0.086 Uiso 1 1 calc R U
H21B H 0.2851 0.4146 0.7767 0.086 Uiso 1 1 calc R U
H21C H 0.4717 0.4624 0.7792 0.086 Uiso 1 1 calc R U
C22 C 0.6136(7) 0.2828(4) 0.9250(3) 0.0566(18) Uani 1 1 d . .
H22A H 0.6928 0.3340 0.9354 0.085 Uiso 1 1 calc R U
H22B H 0.6683 0.2298 0.9503 0.085 Uiso 1 1 calc R U
H22C H 0.5028 0.2954 0.9434 0.085 Uiso 1 1 calc R U
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 77.18(19)
C7 Ir1 C13 120.6(2)
N1 Ir1 C13 101.21(18)
C7 Ir1 C14 99.0(2)
N1 Ir1 C14 130.90(18)
C13 Ir1 C14 38.69(17)
C7 Ir1 C15 112.2(2)
N1 Ir1 C15 165.65(18)
C13 Ir1 C15 64.8(2)
C14 Ir1 C15 39.18(19)
C7 Ir1 C16 148.3(2)
N1 Ir1 C16 134.49(19)
C13 Ir1 C16 62.4(2)
C14 Ir1 C16 62.88(19)
C15 Ir1 C16 37.36(17)
C7 Ir1 C17 158.4(2)
N1 Ir1 C17 104.83(18)
C13 Ir1 C17 37.87(19)
C14 Ir1 C17 63.0(2)
C15 Ir1 C17 62.36(19)
C16 Ir1 C17 35.66(17)
C7 Ir1 Cl1 88.55(14)
N1 Ir1 Cl1 86.60(12)
C13 Ir1 Cl1 150.79(17)
C14 Ir1 Cl1 142.50(15)
C15 Ir1 Cl1 104.06(15)
C16 Ir1 Cl1 92.03(14)
C17 Ir1 Cl1 112.95(15)
C1 N1 C5 118.5(5)
C1 N1 Ir1 126.2(4)
C5 N1 Ir1 115.2(3)
C8 N2 C12 115.0(6)
N1 C1 C2 123.8(6)
C1 C2 C3 119.0(6)
C4 C3 C2 118.9(6)
C3 C4 C5 120.4(5)
N1 C5 C4 119.4(5)
N1 C5 C6 113.8(5)
C4 C5 C6 126.7(5)
C7 C6 C5 116.6(5)
C6 C7 C8 118.5(5)
C6 C7 Ir1 117.1(4)
C8 C7 Ir1 124.4(4)
N2 C8 C9 123.6(5)
N2 C8 C7 116.8(5)
C9 C8 C7 119.6(5)
C10 C9 C8 118.7(6)
C9 C10 C11 118.8(7)
C12 C11 C10 118.1(7)
N2 C12 C11 125.8(7)
C14 C13 C17 107.9(5)
C14 C13 C18 126.1(5)
C17 C13 C18 125.4(5)
C14 C13 Ir1 71.0(3)
C17 C13 Ir1 75.6(3)
C18 C13 Ir1 126.1(4)
C13 C14 C15 107.0(5)
C13 C14 C19 127.0(5)
C15 C14 C19 125.8(5)
C13 C14 Ir1 70.3(3)
C15 C14 Ir1 70.6(3)
C19 C14 Ir1 127.9(4)
C16 C15 C14 107.0(5)
C16 C15 C20 125.5(5)
C14 C15 C20 126.6(5)
C16 C15 Ir1 74.9(3)
C14 C15 Ir1 70.3(3)
C20 C15 Ir1 128.6(4)
C17 C16 C15 110.0(5)
C17 C16 C21 126.7(5)
C15 C16 C21 123.3(5)
C17 C16 Ir1 72.7(3)
C15 C16 Ir1 67.7(3)
C21 C16 Ir1 126.8(4)
C16 C17 C13 107.8(5)
C16 C17 C22 126.1(5)
C13 C17 C22 126.0(5)
C16 C17 Ir1 71.6(3)
C13 C17 Ir1 66.5(3)
C22 C17 Ir1 130.3(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ir1 C7 2.034(5)
Ir1 N1 2.084(4)
Ir1 C13 2.143(5)
Ir1 C14 2.152(5)
Ir1 C15 2.156(5)
Ir1 C16 2.251(5)
Ir1 C17 2.264(5)
Ir1 Cl1 2.3939(15)
N1 C1 1.339(6)
N1 C5 1.366(6)
N2 C8 1.341(7)
N2 C12 1.345(7)
C1 C2 1.350(7)
C2 C3 1.378(7)
C3 C4 1.370(7)
C4 C5 1.400(7)
C5 C6 1.423(6)
C6 C7 1.323(6)
C7 C8 1.485(7)
C8 C9 1.385(7)
C9 C10 1.372(7)
C10 C11 1.381(9)
C11 C12 1.346(9)
C13 C14 1.423(7)
C13 C17 1.435(7)
C13 C18 1.500(7)
C14 C15 1.444(7)
C14 C19 1.494(7)
C15 C16 1.414(7)
C15 C20 1.502(6)
C16 C17 1.382(7)
C16 C21 1.491(7)
C17 C22 1.500(7)
