#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:59:38 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179461 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/58/4335818.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_4335818
loop_
_publ_author_name
'Robert M. Edkins'
'Katharina Fucke'
'Michael J. G. Peach'
'Andrew G. Crawford'
'Todd B. Marder'
'Andrew Beeby'
_publ_section_title
;
 Syntheses, Structures, and Comparison of the Photophysical Properties of
 Cyclometalated Iridium Complexes Containing the Isomeric 1- and
 2-(2'-pyridyl)pyrene Ligands
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              9842
_journal_page_last               9860
_journal_paper_doi               10.1021/ic400819f
_journal_volume                  52
_journal_year                    2013
_chemical_formula_moiety         'C21 H13 N'
_chemical_formula_sum            'C21 H13 N'
_chemical_formula_weight         279.32
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-06-01
_audit_creation_method
;
  Olex2 1.1-alpha
  (compiled 2011.05.17 svn.r1738, GUI svn.r3563)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.715(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.8499(5)
_cell_length_b                   12.6863(15)
_cell_length_c                   27.185(3)
_cell_measurement_reflns_used    1413
_cell_measurement_temperature    393.15
_cell_measurement_theta_max      28.336
_cell_measurement_theta_min      2.196
_cell_volume                     1327.6(3)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
'SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      393.15
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.1100
_diffrn_reflns_av_unetI/netI     0.1313
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12745
_diffrn_reflns_theta_full        30.09
_diffrn_reflns_theta_max         30.09
_diffrn_reflns_theta_min         1.50
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.025
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.879
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3881
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.879
_refine_ls_R_factor_all          0.1426
_refine_ls_R_factor_gt           0.0630
_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)+(0.0712P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1644
_reflns_number_gt                1847
_reflns_number_total             3881
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic400819f_si_002_4.cif
_cod_data_source_block           1-pypyrH
_cod_database_code               4335818
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0624(6) 0.62454(19) 0.07175(9) 0.0294(6) Uani 1 1 d . . .
H1B H -0.0430 0.6652 0.0473 0.035 Uiso 0.499(3) 1 calc PR A 2
H1A H -0.0430 0.6652 0.0473 0.035 Uiso 0.499(3) 1 calc PR A 1
C2 C 0.1607(6) 0.67175(18) 0.11541(9) 0.0271(5) Uani 1 1 d . A .
H2 H 0.1232 0.7433 0.1207 0.033 Uiso 1 1 calc R . .
C3 C 0.3160(6) 0.60984(18) 0.15096(9) 0.0282(5) Uani 1 1 d . . .
H3A H 0.3834 0.6404 0.1807 0.034 Uiso 0.501(3) 1 calc PR A 1
H3B H 0.3834 0.6404 0.1807 0.034 Uiso 0.501(3) 1 calc PR A 2
C5 C 0.2698(5) 0.46112(17) 0.09995(8) 0.0223(5) Uani 1 1 d . . .
C6 C 0.3448(5) 0.34793(17) 0.09051(8) 0.0218(5) Uani 1 1 d . A .
C7 C 0.3013(5) 0.26788(16) 0.12624(8) 0.0199(5) Uani 1 1 d . . .
C8 C 0.1431(5) 0.28560(17) 0.17327(8) 0.0226(5) Uani 1 1 d . A .
H8 H 0.0542 0.3520 0.1804 0.027 Uiso 1 1 calc R . .
C9 C 0.1204(5) 0.20833(17) 0.20729(8) 0.0215(5) Uani 1 1 d . . .
H9 H 0.0158 0.2230 0.2372 0.026 Uiso 1 1 calc R A .
C10 C 0.2529(5) 0.10440(16) 0.19868(8) 0.0198(5) Uani 1 1 d . A .
C11 C 0.2453(5) 0.02474(16) 0.23457(9) 0.0229(5) Uani 1 1 d . . .
H11 H 0.1490 0.0385 0.2651 0.027 Uiso 1 1 calc R A .
C12 C 0.3805(6) -0.07406(17) 0.22469(9) 0.0272(5) Uani 1 1 d . A .
H12 H 0.3803 -0.1255 0.2491 0.033 Uiso 1 1 calc R . .
C13 C 0.5154(6) -0.09717(17) 0.17917(9) 0.0265(5) Uani 1 1 d . . .
H13 H 0.6031 -0.1642 0.1732 0.032 Uiso 1 1 calc R A .
C14 C 0.5221(5) -0.02078(17) 0.14180(8) 0.0227(5) Uani 1 1 d . A .
C15 C 0.6573(6) -0.04186(18) 0.09390(9) 0.0261(5) Uani 1 1 d . . .
H15 H 0.7376 -0.1092 0.0867 0.031 Uiso 1 1 calc R A .
C16 C 0.6713(5) 0.03339(18) 0.05897(9) 0.0271(5) Uani 1 1 d . A .
H16 H 0.7586 0.0168 0.0282 0.032 Uiso 1 1 calc R . .
C17 C 0.5533(5) 0.13911(17) 0.06849(8) 0.0224(5) Uani 1 1 d . . .
C18 C 0.5752(5) 0.21892(18) 0.03344(9) 0.0262(5) Uani 1 1 d . A .
H18 H 0.6578 0.2034 0.0023 0.031 Uiso 1 1 calc R . .
C19 C 0.4759(6) 0.32084(18) 0.04440(9) 0.0268(5) Uani 1 1 d . . .
H19 H 0.4966 0.3728 0.0205 0.032 Uiso 1 1 calc R A .
C20 C 0.4139(5) 0.16293(17) 0.11528(8) 0.0201(5) Uani 1 1 d . A .
C21 C 0.3941(5) 0.08210(16) 0.15172(8) 0.0201(5) Uani 1 1 d . . .
C4B C 0.1154(5) 0.51991(17) 0.06334(8) 0.0264(6) Uani 0.499(3) 1 d P A 2
H4B H 0.0489 0.4892 0.0336 0.032 Uiso 0.499(3) 1 calc PR A 2
C4A C 0.3736(5) 0.50509(16) 0.14380(8) 0.0239(6) Uani 0.501(3) 1 d P A 1
H4A H 0.4808 0.4644 0.1680 0.029 Uiso 0.501(3) 1 calc PR A 1
N1B N 0.3736(5) 0.50509(16) 0.14380(8) 0.0239(6) Uani 0.501(3) 1 d P A 2
N1A N 0.1154(5) 0.51991(17) 0.06334(8) 0.0264(6) Uani 0.499(3) 1 d P A 1
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C4B C1 C2 121.8(2)
C3 C2 C1 118.0(2)
C4A C3 C2 121.8(2)
C4B C5 C6 118.8(2)
C4A C5 C6 119.2(2)
C4A C5 C4B 121.9(2)
C7 C6 C5 123.3(2)
C19 C6 C5 117.7(2)
C19 C6 C7 119.0(2)
C6 C7 C8 123.47(19)
C6 C7 C20 119.0(2)
C20 C7 C8 117.51(19)
C9 C8 C7 121.7(2)
C8 C9 C10 122.0(2)
C11 C10 C9 122.5(2)
C11 C10 C21 119.46(19)
C21 C10 C9 118.0(2)
C12 C11 C10 120.3(2)
C13 C12 C11 120.9(2)
C12 C13 C14 120.8(2)
C13 C14 C15 122.6(2)
C13 C14 C21 119.1(2)
C21 C14 C15 118.3(2)
C16 C15 C14 121.7(2)
C15 C16 C17 121.2(2)
C18 C17 C16 122.1(2)
C18 C17 C20 119.0(2)
C20 C17 C16 118.9(2)
C19 C18 C17 120.9(2)
C18 C19 C6 121.8(2)
C17 C20 C7 120.2(2)
C17 C20 C21 119.52(19)
C21 C20 C7 120.3(2)
C10 C21 C20 120.27(19)
C14 C21 C10 119.3(2)
C14 C21 C20 120.4(2)
C1 C4B C5 118.2(2)
C3 C4A C5 118.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.378(3)
C1 C4B 1.363(3)
C2 C3 1.376(3)
C3 C4A 1.362(3)
C5 C6 1.488(3)
C5 C4B 1.373(3)
C5 C4A 1.371(3)
C6 C7 1.417(3)
C6 C19 1.400(3)
C7 C8 1.441(3)
C7 C20 1.433(3)
C8 C9 1.351(3)
C9 C10 1.434(3)
C10 C11 1.405(3)
C10 C21 1.422(3)
C11 C12 1.385(3)
C12 C13 1.379(3)
C13 C14 1.404(3)
C14 C15 1.434(3)
C14 C21 1.422(3)
C15 C16 1.348(3)
C16 C17 1.440(3)
C17 C18 1.394(3)
C17 C20 1.419(3)
C18 C19 1.382(3)
C20 C21 1.428(3)
