#------------------------------------------------------------------------------
#$Date: 2018-08-16 18:56:10 +0300 (Thu, 16 Aug 2018) $
#$Revision: 209813 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/07/49/4074990.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_4074990
loop_
_publ_author_name
'Ionkin, Alex S.'
'Marshall, William J.'
'Fish, Brian M.'
_publ_section_title
;
 Synthesis and Structural Characterization of a Series of Novel
 Polyaromatic Ligands Containing Pyrene and Related Biscyclometalated
 Iridium(III) Complexes
;
_journal_coden_ASTM              ORGND7
_journal_issue                   6
_journal_name_full               Organometallics
_journal_page_first              1461
_journal_page_last               1471
_journal_paper_doi               10.1021/om0510775
_journal_volume                  25
_journal_year                    2006
_chemical_formula_sum            'C12 H10 Cl N'
_chemical_formula_weight         203.66
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4452(10)
_cell_length_b                   10.9266(15)
_cell_length_c                   12.0699(16)
_cell_measurement_temperature    293(2)
_cell_volume                     981.9(2)
_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      293(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  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0720
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7915
_diffrn_reflns_theta_full        29.12
_diffrn_reflns_theta_max         29.12
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.343
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       wedge
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.20(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2596
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0418
_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)+(0.0506P)²+0.0165P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1149
_reflns_number_gt                2000
_reflns_number_total             2596
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om0510775si20060112_022917.cif
_cod_data_source_block           04226
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      Pca2(1)
_cod_database_code               4074990
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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
Cl1 Cl 0.02565(7) 0.20162(6) 0.62876(7) 0.03800(18) Uani 1 1 d .
N1 N 0.1154(3) 0.39172(16) 1.02127(15) 0.0256(4) Uani 1 1 d .
C1 C -0.0245(3) 0.2064(2) 0.95899(19) 0.0210(4) Uani 1 1 d .
C2 C 0.0173(3) 0.2383(2) 0.8496(2) 0.0226(5) Uani 1 1 d .
H2A H 0.0746 0.3120 0.8346 0.027 Uiso 1 1 calc R
C3 C -0.0269(3) 0.1598(2) 0.76418(19) 0.0245(5) Uani 1 1 d .
C4 C -0.1107(3) 0.0484(2) 0.7832(2) 0.0282(5) Uani 1 1 d .
H4A H -0.1395 -0.0033 0.7246 0.034 Uiso 1 1 calc R
C5 C -0.1502(3) 0.0164(2) 0.8908(2) 0.0304(5) Uani 1 1 d .
H5A H -0.2063 -0.0580 0.9052 0.037 Uiso 1 1 calc R
C6 C -0.1072(3) 0.09373(19) 0.97772(19) 0.0261(5) Uani 1 1 d .
H6A H -0.1341 0.0702 1.0499 0.031 Uiso 1 1 calc R
C7 C 0.0247(3) 0.2912(2) 1.0507(2) 0.0217(5) Uani 1 1 d .
C8 C 0.1626(3) 0.46896(19) 1.10182(19) 0.0294(6) Uani 1 1 d .
H8A H 0.2264 0.5389 1.0823 0.035 Uiso 1 1 calc R
C9 C 0.1225(3) 0.4513(2) 1.2127(2) 0.0298(5) Uani 1 1 d .
H9A H 0.1593 0.5079 1.2655 0.036 Uiso 1 1 calc R
C10 C 0.0272(3) 0.3486(3) 1.2438(2) 0.0256(5) Uani 1 1 d .
C11 C -0.0228(3) 0.2681(2) 1.1603(2) 0.0243(5) Uani 1 1 d .
H11A H -0.0885 0.1983 1.1778 0.029 Uiso 1 1 calc R
C12 C -0.0204(3) 0.3259(3) 1.3630(2) 0.0334(6) Uani 1 1 d .
H12A H 0.0853 0.3339 1.4080 0.050 Uiso 1 1 calc R
H12B H -0.0682 0.2447 1.3707 0.050 Uiso 1 1 calc R
H12C H -0.1086 0.3845 1.3864 0.050 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0476(3) 0.0426(3) 0.0237(3) -0.0020(3) 0.0010(4) -0.0058(2)
N1 0.0283(10) 0.0248(10) 0.0238(10) 0.0011(8) 0.0005(8) -0.0030(8)
C1 0.0186(9) 0.0223(10) 0.0221(12) 0.0023(9) -0.0004(9) 0.0020(8)
C2 0.0229(10) 0.0211(10) 0.0239(12) -0.0005(9) 0.0006(9) 0.0008(8)
C3 0.0247(10) 0.0279(11) 0.0209(12) 0.0009(10) 0.0001(9) 0.0030(9)
C4 0.0293(11) 0.0251(11) 0.0302(13) -0.0052(10) -0.0044(10) -0.0012(9)
C5 0.0331(12) 0.0228(11) 0.0354(15) -0.0010(10) -0.0003(10) -0.0049(8)
C6 0.0294(11) 0.0238(11) 0.0250(12) -0.0002(9) 0.0024(9) -0.0038(9)
C7 0.0202(10) 0.0216(11) 0.0232(12) -0.0029(9) -0.0003(10) 0.0022(9)
C8 0.0328(11) 0.0229(11) 0.0325(16) -0.0009(9) -0.0004(10) -0.0046(8)
C9 0.0324(13) 0.0309(13) 0.0262(13) -0.0072(10) -0.0026(10) -0.0039(10)
C10 0.0218(10) 0.0303(12) 0.0246(12) -0.0014(10) -0.0021(10) 0.0034(9)
C11 0.0238(11) 0.0244(11) 0.0247(13) 0.0015(9) -0.0006(9) 0.0006(8)
C12 0.0330(12) 0.0424(14) 0.0248(13) -0.0054(12) 0.0020(10) -0.0018(10)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 N1 C7 117.3(2)
C6 C1 C2 118.0(2)
C6 C1 C7 122.5(2)
C2 C1 C7 119.46(18)
C3 C2 C1 119.8(2)
C2 C3 C4 121.9(2)
C2 C3 Cl1 119.00(19)
C4 C3 Cl1 119.09(19)
C5 C4 C3 118.4(2)
C4 C5 C6 120.7(2)
C5 C6 C1 121.2(2)
N1 C7 C11 122.0(2)
N1 C7 C1 115.9(2)
C11 C7 C1 122.09(18)
N1 C8 C9 124.0(2)
C10 C9 C8 119.2(2)
C9 C10 C11 117.2(2)
C9 C10 C12 121.1(2)
C11 C10 C12 121.8(2)
C10 C11 C7 120.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C3 1.742(2)
N1 C8 1.335(3)
N1 C7 1.338(3)
C1 C6 1.395(3)
C1 C2 1.400(3)
C1 C7 1.489(3)
C2 C3 1.380(3)
C3 C4 1.387(3)
C4 C5 1.377(3)
C5 C6 1.385(3)
C7 C11 1.392(4)
C8 C9 1.384(3)
C9 C10 1.380(3)
C10 C11 1.388(3)
C10 C12 1.503(4)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 1.2(3)
C7 C1 C2 C3 179.63(19)
C1 C2 C3 C4 -0.7(3)
C1 C2 C3 Cl1 179.80(15)
C2 C3 C4 C5 0.0(3)
Cl1 C3 C4 C5 179.55(17)
C3 C4 C5 C6 0.0(3)
C4 C5 C6 C1 0.6(4)
C2 C1 C6 C5 -1.2(3)
C7 C1 C6 C5 -179.53(19)
C8 N1 C7 C11 1.4(3)
C8 N1 C7 C1 -179.44(19)
C6 C1 C7 N1 175.2(2)
C2 C1 C7 N1 -3.2(2)
C6 C1 C7 C11 -5.6(3)
C2 C1 C7 C11 176.0(2)
C7 N1 C8 C9 -0.4(3)
N1 C8 C9 C10 -0.3(4)
C8 C9 C10 C11 0.1(3)
C8 C9 C10 C12 -179.7(2)
C9 C10 C11 C7 0.8(3)
C12 C10 C11 C7 -179.4(2)
N1 C7 C11 C10 -1.6(4)
C1 C7 C11 C10 179.25(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9818863
