#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:04:08 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179438 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/35/4333585.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_4333585
loop_
_publ_author_name
'Edwin C. Constable'
'Markus Neuburger'
'Pirmin Rösel'
'Gabriel E. Schneider'
'Jennifer A. Zampese'
'Catherine E. Housecroft'
'Filippo Monti'
'Nicola Armaroli'
'Rubén D. Costa'
'Enrique Ortí'
_publ_section_title
;
 Ligand-Based Charge-Transfer Luminescence in Ionic Cyclometalated
 Iridium(III) Complexes Bearing a Pyrene-Functionalized Bipyridine Ligand:
 A Joint Theoretical and Experimental Study
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              885
_journal_page_last               897
_journal_paper_doi               10.1021/ic302026f
_journal_volume                  52
_journal_year                    2013
_chemical_formula_moiety         'C42 H24 N2'
_chemical_formula_sum            'C42 H24 N2'
_chemical_formula_weight         556.67
_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
_audit_creation_date             08-05-27
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 94.21(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.378(3)
_cell_length_b                   6.923(3)
_cell_length_c                   26.070(12)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    173
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1328.0(10)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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      173
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.149
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            13452
_diffrn_reflns_theta_full        25.466
_diffrn_reflns_theta_max         28.614
_diffrn_reflns_theta_min         3.045
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       plate
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.45
_refine_diff_density_min         -0.50
_refine_ls_extinction_coef       180(50)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         1624
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1911
_refine_ls_R_factor_gt           0.1048
_refine_ls_shift/su_max          0.002778
_refine_ls_structure_factor_coef F
_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: 
 2.24 0.668E-01 1.70 -0.151 -0.622E-01 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1196
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0791
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              34
_reflns_limit_l_min              0
_reflns_number_gt                1624
_reflns_number_total             3235
_reflns_threshold_expression     I>0.9σ(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          0.654(3)
_oxford_structure_analysis_title 'pr352_173k_0ma in P2(1)/c'
_cod_data_source_file            ic302026f_si_001_1.cif
_cod_data_source_block           pr352_173k
_cod_original_cell_volume        1328.1(10)
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               4333585
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
C1 C 0.4321(5) 0.4338(5) 0.48685(15) 0.0231 1.0000 Uani .
C2 C 0.2574(6) 0.4922(5) 0.47187(15) 0.0307 1.0000 Uani .
C3 C 0.1399(6) 0.3633(6) 0.44764(15) 0.0320 1.0000 Uani .
C4 C 0.1946(5) 0.1765(5) 0.43829(15) 0.0276 1.0000 Uani .
C5 C 0.3718(6) 0.1305(5) 0.45580(16) 0.0292 1.0000 Uani .
C6 C 0.0737(5) 0.0252(5) 0.41560(15) 0.0266 1.0000 Uani .
C7 C -0.1018(5) 0.0032(6) 0.43270(16) 0.0320 1.0000 Uani .
C8 C -0.2106(6) -0.1484(6) 0.41701(16) 0.0329 1.0000 Uani .
C9 C -0.1523(5) -0.2899(6) 0.38441(16) 0.0288 1.0000 Uani .
C10 C -0.2579(5) -0.4571(5) 0.37036(17) 0.0321 1.0000 Uani .
C11 C -0.1951(6) -0.5937(6) 0.33987(17) 0.0363 1.0000 Uani .
C12 C -0.0193(6) -0.5765(6) 0.31913(16) 0.0291 1.0000 Uani .
C13 C 0.0469(6) -0.7181(6) 0.28801(16) 0.0359 1.0000 Uani .
C14 C 0.2161(7) -0.6978(7) 0.26809(18) 0.0424 1.0000 Uani .
C15 C 0.3218(6) -0.5368(6) 0.27974(17) 0.0351 1.0000 Uani .
C16 C 0.2589(5) -0.3924(6) 0.31151(15) 0.0289 1.0000 Uani .
C17 C 0.0860(5) -0.4111(6) 0.33151(15) 0.0278 1.0000 Uani .
C18 C 0.0215(5) -0.2668(6) 0.36476(14) 0.0257 1.0000 Uani .
C19 C 0.1348(5) -0.1087(5) 0.37920(15) 0.0258 1.0000 Uani .
C20 C 0.3041(5) -0.0885(5) 0.35565(15) 0.0276 1.0000 Uani .
C21 C 0.3636(6) -0.2229(6) 0.32340(15) 0.0322 1.0000 Uani .
N1 N 0.4913(5) 0.2522(5) 0.47917(12) 0.0298 1.0000 Uani .
H21 H 0.2213 0.6205 0.4781 0.0363 1.0000 Uiso R
H31 H 0.0206 0.4004 0.4377 0.0375 1.0000 Uiso R
H51 H 0.4120 0.0020 0.4510 0.0352 1.0000 Uiso R
H71 H -0.1451 0.0951 0.4555 0.0384 1.0000 Uiso R
H81 H -0.3272 -0.1581 0.4288 0.0403 1.0000 Uiso R
H101 H -0.3724 -0.4712 0.3824 0.0384 1.0000 Uiso R
H111 H -0.2664 -0.7046 0.3318 0.0433 1.0000 Uiso R
H131 H -0.0239 -0.8271 0.2799 0.0424 1.0000 Uiso R
H141 H 0.2601 -0.7924 0.2468 0.0500 1.0000 Uiso R
H151 H 0.4361 -0.5246 0.2664 0.0419 1.0000 Uiso R
H201 H 0.3760 0.0213 0.3630 0.0325 1.0000 Uiso R
H211 H 0.4738 -0.2057 0.3087 0.0388 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 0.0033 0.0016 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 0.0061 0.0033 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'
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
_geom_angle_publ_flag
C1 2_666 C1 C2 122.3(4) yes
C1 2_666 C1 N1 115.3(4) yes
C2 . C1 N1 122.4(3) yes
C1 . C2 C3 119.2(3) yes
C1 . C2 H21 119.8 no
C3 . C2 H21 121.0 no
C2 . C3 C4 120.6(4) yes
C2 . C3 H31 120.1 no
C4 . C3 H31 119.3 no
C3 . C4 C5 115.9(4) yes
C3 . C4 C6 124.1(4) yes
C5 . C4 C6 119.8(3) yes
C4 . C5 N1 125.4(3) yes
C4 . C5 H51 117.8 no
N1 . C5 H51 116.7 no
C4 . C6 C7 119.6(4) yes
C4 . C6 C19 121.3(4) yes
C7 . C6 C19 119.0(3) yes
C6 . C7 C8 121.5(4) yes
C6 . C7 H71 119.3 no
C8 . C7 H71 119.3 no
C7 . C8 C9 121.7(4) yes
C7 . C8 H81 119.3 no
C9 . C8 H81 119.0 no
C8 . C9 C10 122.8(4) yes
C8 . C9 C18 118.0(4) yes
C10 . C9 C18 119.2(4) yes
C9 . C10 C11 121.2(4) yes
C9 . C10 H101 119.4 no
C11 . C10 H101 119.4 no
C10 . C11 C12 121.5(4) yes
C10 . C11 H111 119.6 no
C12 . C11 H111 118.9 no
C11 . C12 C13 121.7(4) yes
C11 . C12 C17 118.5(4) yes
C13 . C12 C17 119.8(4) yes
C12 . C13 C14 120.8(4) yes
C12 . C13 H131 119.3 no
C14 . C13 H131 119.9 no
C13 . C14 C15 120.4(4) yes
C13 . C14 H141 120.8 no
C15 . C14 H141 118.8 no
C14 . C15 C16 120.1(4) yes
C14 . C15 H151 119.9 no
C16 . C15 H151 120.0 no
C15 . C16 C17 119.9(4) yes
C15 . C16 C21 121.3(4) yes
C17 . C16 C21 118.8(4) yes
C16 . C17 C12 119.1(4) yes
C16 . C17 C18 120.6(3) yes
C12 . C17 C18 120.4(4) yes
C17 . C18 C9 119.3(4) yes
C17 . C18 C19 119.2(4) yes
C9 . C18 C19 121.5(4) yes
C6 . C19 C18 118.2(4) yes
C6 . C19 C20 123.3(3) yes
C18 . C19 C20 118.5(4) yes
C19 . C20 C21 122.1(4) yes
C19 . C20 H201 119.2 no
C21 . C20 H201 118.7 no
C16 . C21 C20 120.5(4) yes
C16 . C21 H211 119.4 no
C20 . C21 H211 120.1 no
C1 . N1 C5 116.4(3) 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 C1 2_666 1.487(7) yes
C1 C2 . 1.380(5) yes
C1 N1 . 1.351(4) yes
C2 C3 . 1.366(6) yes
C2 H21 . 0.945 no
C3 C4 . 1.382(5) yes
C3 H31 . 0.935 no
C4 C5 . 1.389(5) yes
C4 C6 . 1.472(5) yes
C5 N1 . 1.334(5) yes
C5 H51 . 0.949 no
C6 C7 . 1.408(6) yes
C6 C19 . 1.424(5) yes
C7 C8 . 1.366(6) yes
C7 H71 . 0.942 no
C8 C9 . 1.386(6) yes
C8 H81 . 0.937 no
C9 C10 . 1.428(5) yes
C9 C18 . 1.425(5) yes
C10 C11 . 1.340(6) yes
C10 H101 . 0.927 no
C11 C12 . 1.446(6) yes
C11 H111 . 0.945 no
C12 C13 . 1.384(6) yes
C12 C17 . 1.408(5) yes
C13 C14 . 1.394(7) yes
C13 H131 . 0.933 no
C14 C15 . 1.381(6) yes
C14 H141 . 0.931 no
C15 C16 . 1.399(6) yes
C15 H151 . 0.939 no
C16 C17 . 1.419(5) yes
C16 C21 . 1.426(5) yes
C17 C18 . 1.427(5) yes
C18 C19 . 1.412(5) yes
C19 C20 . 1.438(5) yes
C20 C21 . 1.349(5) yes
C20 H201 . 0.939 no
C21 H211 . 0.932 no
