#------------------------------------------------------------------------------
#$Date: 2017-03-04 06:38:26 +0200 (Sat, 04 Mar 2017) $
#$Revision: 193051 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/56/4125654.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_4125654
loop_
_publ_author_name
'Ertl, Cathrin D.'
'Momblona, Cristina'
'Pertegás, Antonio'
'Junquera-Hernández, José M'
'La-Placa, Maria-Grazia'
'Prescimone, Alessandro'
'Ortí, Enrique'
'Housecroft, Catherine E.'
'Constable, Edwin C.'
'Bolink, Henk J.'
_publ_section_title
;
 Highly Stable Red-Light-Emitting Electrochemical Cells.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3237
_journal_page_last               3248
_journal_paper_doi               10.1021/jacs.6b13311
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_compound_source        'Cathrin Ertl'
_chemical_formula_moiety         'C34 H24 F6 Ir1 N6 P1 S2'
_chemical_formula_sum            'C34 H24 F6 Ir N6 P S2'
_chemical_formula_weight         917.92
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2015-11-10
_audit_creation_method           CRYSTALS_ver_14.61_build_5555
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.2991(19)
_cell_length_b                   13.340(2)
_cell_length_c                   40.350(7)
_cell_measurement_reflns_used    9990
_cell_measurement_temperature    123
_cell_measurement_theta_max      69
_cell_measurement_theta_min      5
_cell_volume                     6620.2(18)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      123
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            10929
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         70.020
_diffrn_reflns_theta_min         5.012
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    10.068
_exptl_absorpt_correction_T_max  0.67
_exptl_absorpt_correction_T_min  0.47
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.842
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3584
_exptl_crystal_recrystallization_method
; 
 DCM / Et2O
;
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.41
_refine_diff_density_min         -0.35
_refine_ls_abs_structure_details 'Flack (1983), 1009 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.032(8)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9244
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2557
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0171
_refine_ls_R_factor_gt           0.0170
_refine_ls_shift/su_max          0.0004386
_refine_ls_shift/su_mean         0.0000515
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 2.40 3.27 1.16 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0405
_refine_ls_wR_factor_gt          0.0405
_refine_ls_wR_factor_ref         0.0405
_reflns_limit_h_max              14
_reflns_limit_h_min              0
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              37
_reflns_limit_l_min              -48
_reflns_number_gt                2553
_reflns_number_total             2564
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   1.10
_oxford_diffrn_Wilson_scale      1323.61
_oxford_refine_ls_r_factor_ref   0.0171
_oxford_refine_ls_scale          0.0299995(16)
_oxford_reflns_number_all        2557
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'Fdd2 in Fdd2'
_cod_data_source_file            ja6b13311_si_004.cif
_cod_data_source_block           CE431a_123K
_cod_original_cell_volume        6620.3(18)
_cod_original_sg_symbol_H-M      'F d d 2 '
_cod_original_formula_sum        'C34 H24 F6 Ir1 N6 P1 S2'
_cod_database_code               4125654
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x,y+1/2,z+1/2
x+1/2,y,z+1/2
x+1/2,y+1/2,z
-x+1/4,y+1/4,z+1/4
-x+1/4,y+3/4,z+3/4
-x+3/4,y+1/4,z+3/4
-x+3/4,y+3/4,z+1/4
x+1/4,-y+1/4,z+1/4
x+1/4,-y+3/4,z+3/4
x+3/4,-y+1/4,z+3/4
x+3/4,-y+3/4,z+1/4
-x+1/2,-y,z+1/2
-x+1/2,-y+1/2,z+1
-x+1,-y,z+1
-x+1,-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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C -0.1786(2) -0.9436(2) 0.54107(9) 0.0147 1.0000 Uani . .
C2 C -0.1563(3) -1.0136(2) 0.51613(11) 0.0215 1.0000 Uani . .
C3 C -0.1187(3) -1.1064(2) 0.52605(10) 0.0258 1.0000 Uani . .
C4 C -0.1027(3) -1.1311(3) 0.55908(10) 0.0307 1.0000 Uani . .
C5 C -0.1222(3) -1.0631(3) 0.58368(11) 0.0297 1.0000 Uani . .
C6 C -0.1620(3) -0.9684(3) 0.57455(9) 0.0215 1.0000 Uani . .
C7 C -0.2294(3) -0.8009(3) 0.56533(9) 0.0171 1.0000 Uani . .
C8 C -0.2155(3) -0.5845(2) 0.44207(9) 0.0185 1.0000 Uani . .
C9 C -0.2511(3) -0.5257(3) 0.41533(11) 0.0248 1.0000 Uani . .
C10 C -0.3548(3) -0.5387(2) 0.40301(10) 0.0231 1.0000 Uani . .
C11 C -0.4248(3) -0.6076(2) 0.41712(9) 0.0231 1.0000 Uani . .
C12 C -0.3903(2) -0.6653(2) 0.44402(8) 0.0170 1.0000 Uani . .
C13 C -0.4587(3) -0.7375(2) 0.46116(10) 0.0179 1.0000 Uani . .
C14 C -0.5642(3) -0.7662(3) 0.45192(11) 0.0223 1.0000 Uani . .
C15 C -0.6216(2) -0.8332(2) 0.47113(10) 0.0239 1.0000 Uani . .
C16 C -0.5754(2) -0.8712(2) 0.49986(10) 0.0224 1.0000 Uani . .
C17 C -0.4706(3) -0.8426(2) 0.50776(9) 0.0172 1.0000 Uani . .
Ir1 Ir -0.2500 -0.7500 0.49387(4) 0.0126 1.0000 Uani S T
N1 N -0.2177(2) -0.8458(2) 0.53655(8) 0.0150 1.0000 Uani . .
S1 S -0.19432(6) -0.86840(5) 0.59993(4) 0.0239 1.0000 Uani . .
N2 N -0.2826(3) -0.6546(2) 0.45681(9) 0.0266 1.0000 Uani . .
N3 N -0.41271(18) -0.77841(19) 0.48903(8) 0.0150 1.0000 Uani . .
P1 P 0.0000 -0.5000 0.59817(6) 0.0301 1.0000 Uani S T
F1 F -0.0200(2) -0.6182(2) 0.59741(10) 0.0610 1.0000 Uani . .
F3 F -0.0925(3) -0.4861(3) 0.62522(10) 0.0834 1.0000 Uani . .
F2 F -0.0899(2) -0.48959(19) 0.56987(8) 0.0416 1.0000 Uani . .
H21 H -0.1667 -0.9984 0.4939 0.0290 1.0000 Uiso R .
H31 H -0.1042 -1.1543 0.5099 0.0310 1.0000 Uiso R .
H41 H -0.0780 -1.1949 0.5646 0.0390 1.0000 Uiso R .
H51 H -0.1095 -1.0784 0.6058 0.0360 1.0000 Uiso R .
H81 H -0.1455 -0.5752 0.4502 0.0230 1.0000 Uiso R .
H91 H -0.2054 -0.4779 0.4060 0.0300 1.0000 Uiso R .
H101 H -0.3774 -0.5012 0.3849 0.0270 1.0000 Uiso R .
H111 H -0.4943 -0.6157 0.4085 0.0290 1.0000 Uiso R .
H141 H -0.5954 -0.7396 0.4329 0.0290 1.0000 Uiso R .
H151 H -0.6909 -0.8534 0.4648 0.0290 1.0000 Uiso R .
H161 H -0.6142 -0.9144 0.5136 0.0290 1.0000 Uiso R .
H171 H -0.4386 -0.8682 0.5269 0.0220 1.0000 Uiso R .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.2955 0.4335 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Ir -4.7710 6.5667 27.3049 1.5928 16.7296 8.8655 15.6115 0.4179 5.8338 45.0011
11.4722 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 C6 . 120.4(3) yes
C2 . C1 N1 . 126.4(3) yes
C6 . C1 N1 . 113.2(3) yes
C1 . C2 C3 . 117.1(4) yes
C1 . C2 H21 . 121.5 no
C3 . C2 H21 . 121.4 no
C2 . C3 C4 . 122.7(4) yes
C2 . C3 H31 . 118.5 no
C4 . C3 H31 . 118.8 no
C3 . C4 C5 . 121.0(3) yes
C3 . C4 H41 . 119.5 no
C5 . C4 H41 . 119.5 no
C4 . C5 C6 . 117.9(3) yes
C4 . C5 H51 . 121.6 no
C6 . C5 H51 . 120.5 no
C1 . C6 C5 . 120.9(3) yes
C1 . C6 S1 . 110.8(2) yes
C5 . C6 S1 . 128.3(3) yes
C7 14_434 C7 N1 . 117.71(19) yes
C7 14_434 C7 S1 . 125.39(12) yes
N1 . C7 S1 . 116.9(3) yes
C9 . C8 N2 . 121.5(3) yes
C9 . C8 H81 . 119.1 no
N2 . C8 H81 . 119.4 no
C8 . C9 C10 . 119.7(3) yes
C8 . C9 H91 . 120.4 no
C10 . C9 H91 . 119.9 no
C9 . C10 C11 . 120.7(3) yes
C9 . C10 H101 . 119.6 no
C11 . C10 H101 . 119.7 no
C10 . C11 C12 . 119.8(3) yes
C10 . C11 H111 . 119.7 no
C12 . C11 H111 . 120.4 no
C11 . C12 C13 . 124.0(3) yes
C11 . C12 N2 . 120.4(3) yes
C13 . C12 N2 . 115.6(3) yes
C12 . C13 C14 . 126.1(3) yes
C12 . C13 N3 . 114.5(3) yes
C14 . C13 N3 . 119.3(3) yes
C13 . C14 C15 . 120.1(3) yes
C13 . C14 H141 . 119.7 no
C15 . C14 H141 . 120.2 no
C14 . C15 C16 . 119.9(3) yes
C14 . C15 H151 . 120.2 no
C16 . C15 H151 . 120.0 no
C15 . C16 C17 . 118.3(3) yes
C15 . C16 H161 . 120.9 no
C17 . C16 H161 . 120.8 no
C16 . C17 N3 . 122.6(3) yes
C16 . C17 H171 . 118.9 no
N3 . C17 H171 . 118.4 no
N1 14_434 Ir1 N3 14_434 98.34(11) yes
N1 14_434 Ir1 N2 14_434 176.11(13) yes
N3 14_434 Ir1 N2 14_434 81.42(13) yes
N1 14_434 Ir1 N1 . 75.72(15) yes
N3 14_434 Ir1 N1 . 90.33(10) yes
N2 14_434 Ir1 N1 . 100.39(10) yes
N1 14_434 Ir1 N2 . 100.39(10) yes
N3 14_434 Ir1 N2 . 90.39(13) yes
N2 14_434 Ir1 N2 . 83.50(18) yes
N1 . Ir1 N2 . 176.11(13) yes
N1 14_434 Ir1 N3 . 90.33(10) yes
N3 14_434 Ir1 N3 . 169.04(16) yes
N2 14_434 Ir1 N3 . 90.39(13) yes
N1 . Ir1 N3 . 98.34(11) yes
N2 . Ir1 N3 . 81.42(13) yes
Ir1 . N1 C1 . 135.3(2) yes
Ir1 . N1 C7 . 114.2(2) yes
C1 . N1 C7 . 110.3(3) yes
C6 . S1 C7 . 88.87(17) yes
C12 . N2 C8 . 117.8(3) yes
C12 . N2 Ir1 . 113.0(2) yes
C8 . N2 Ir1 . 129.1(3) yes
Ir1 . N3 C13 . 114.1(2) yes
Ir1 . N3 C17 . 125.5(2) yes
C13 . N3 C17 . 119.7(3) yes
F1 15_444 P1 F2 15_444 88.03(16) yes
F1 15_444 P1 F3 15_444 91.0(2) yes
F2 15_444 P1 F3 15_444 89.18(19) yes
F1 15_444 P1 F1 . 177.8(3) yes
F2 15_444 P1 F1 . 90.39(17) yes
F3 15_444 P1 F1 . 90.48(19) yes
F1 15_444 P1 F3 . 90.48(19) yes
F2 15_444 P1 F3 . 177.3(2) yes
F3 15_444 P1 F3 . 93.1(3) yes
F1 . P1 F3 . 91.0(2) yes
F1 15_444 P1 F2 . 90.39(17) yes
F2 15_444 P1 F2 . 88.6(2) yes
F3 15_444 P1 F2 . 177.3(2) yes
F1 . P1 F2 . 88.03(16) yes
F3 . P1 F2 . 89.18(19) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.400(5) yes
C1 C6 . 1.406(4) yes
C1 N1 . 1.402(4) yes
C2 C3 . 1.380(5) yes
C2 H21 . 0.930 no
C3 C4 . 1.387(5) yes
C3 H31 . 0.930 no
C4 C5 . 1.366(6) yes
C4 H41 . 0.930 no
C5 C6 . 1.405(5) yes
C5 H51 . 0.930 no
C6 S1 . 1.728(4) yes
C7 C7 14_434 1.451(7) yes
C7 N1 . 1.314(4) yes
C7 S1 . 1.716(4) yes
C8 C9 . 1.403(5) yes
C8 N2 . 1.382(5) yes
C8 H81 . 0.930 no
C9 C10 . 1.380(5) yes
C9 H91 . 0.930 no
C10 C11 . 1.382(5) yes
C10 H101 . 0.930 no
C11 C12 . 1.397(4) yes
C11 H111 . 0.930 no
C12 C13 . 1.454(5) yes
C12 N2 . 1.429(4) yes
C13 C14 . 1.404(5) yes
C13 N3 . 1.372(5) yes
C14 C15 . 1.377(5) yes
C14 H141 . 0.930 no
C15 C16 . 1.387(5) yes
C15 H151 . 0.930 no
C16 C17 . 1.382(4) yes
C16 H161 . 0.930 no
C17 N3 . 1.346(4) yes
C17 H171 . 0.930 no
Ir1 N1 14_434 2.181(3) yes
Ir1 N3 14_434 2.046(2) yes
Ir1 N2 14_434 2.005(3) yes
Ir1 N1 . 2.181(3) yes
Ir1 N2 . 2.005(3) yes
Ir1 N3 . 2.046(2) yes
P1 F1 15_444 1.596(3) yes
P1 F2 15_444 1.595(3) yes
P1 F3 15_444 1.587(4) yes
P1 F1 . 1.596(3) yes
P1 F3 . 1.587(4) yes
P1 F2 . 1.595(3) yes
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
2 6 -20 x
0 8 0 x
3 1 -3 x
0 4 24 x
6 4 -4 x
1 3 -5 x
6 6 2 x
