#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:36:50 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180229 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/15/7111568.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7111568
loop_
_publ_author_name
'Wen, Bo'
'Petersen, Jeffrey L.'
'Wang, Kung K.'
_publ_section_title
;
 Synthesis of 4,5-diheteroarylphenanthrenes and their dinuclear
 ruthenium(ii) bis(2,2′:6′,2″-terpyridine) complexes
 possessing severe helical twists
;
_journal_issue                   11
_journal_name_full               'Chemical Communications'
_journal_page_first              1938
_journal_page_last               1940
_journal_paper_doi               10.1039/b921667g
_journal_volume                  46
_journal_year                    2010
_chemical_formula_sum            'C46 H40 N2'
_chemical_formula_weight         620.80
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 116.370(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.9360(11)
_cell_length_b                   10.3982(7)
_cell_length_c                   20.0030(13)
_cell_measurement_reflns_used    6470
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.27
_cell_volume                     3342.4(4)
_computing_cell_refinement       'SMART version 5.6'
_computing_data_collection       'SMART version 5.6'
_computing_data_reduction        'SAINT version 5/6.0'
_computing_publication_material  'SHELXTL 6.1'
_computing_structure_refinement  'SHELXTL 6.1'
_computing_structure_solution    'SHELXTL 6.1'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Siemens P4 automated diffractometer'
_diffrn_measurement_method       'Smart 1K CCD detector'
_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  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0718
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11121
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.27
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular crstyalline fragment'
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3820
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0554
_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)+(0.0635P)²+1.8237P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1605
_reflns_number_gt                3052
_reflns_number_total             3820
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b921667gsup1.cif
_cod_data_source_block           bw7ccd
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7111568
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
N1 N 0.16446(13) 0.16880(19) 0.39840(12) 0.0695(5) Uani 1 1 d .
C1 C 0.00610(11) 0.78913(14) 0.21912(10) 0.0422(4) Uani 1 1 d .
H1 H 0.0046 0.8671 0.1958 0.051 Uiso 1 1 calc R
C2 C 0.02139(9) 0.67353(13) 0.18782(9) 0.0344(3) Uani 1 1 d .
C3 C 0.04584(10) 0.67354(14) 0.12838(9) 0.0369(3) Uani 1 1 d .
C4 C 0.08749(9) 0.56451(14) 0.12276(9) 0.0364(3) Uani 1 1 d .
C5 C 0.13119(11) 0.54096(16) 0.07389(10) 0.0467(4) Uani 1 1 d .
H5A H 0.0912 0.5277 0.0223 0.056 Uiso 1 1 calc R
H5B H 0.1669 0.6128 0.0765 0.056 Uiso 1 1 calc R
C6 C 0.18113(10) 0.42207(16) 0.10598(10) 0.0430(4) Uani 1 1 d .
C7 C 0.23647(12) 0.36343(18) 0.08427(12) 0.0538(5) Uani 1 1 d .
H7 H 0.2449 0.3968 0.0450 0.065 Uiso 1 1 calc R
C8 C 0.27863(12) 0.2552(2) 0.12167(12) 0.0588(5) Uani 1 1 d .
H8 H 0.3149 0.2138 0.1070 0.071 Uiso 1 1 calc R
C9 C 0.26702(12) 0.2080(2) 0.18104(12) 0.0577(5) Uani 1 1 d .
H9 H 0.2965 0.1356 0.2064 0.069 Uiso 1 1 calc R
C10 C 0.21240(11) 0.26645(18) 0.20330(11) 0.0492(4) Uani 1 1 d .
H10 H 0.2058 0.2343 0.2437 0.059 Uiso 1 1 calc R
C11 C 0.16730(9) 0.37404(15) 0.16463(9) 0.0380(4) Uani 1 1 d .
C12 C 0.10512(9) 0.45884(14) 0.17341(8) 0.0332(3) Uani 1 1 d .
C13 C 0.06972(8) 0.45178(13) 0.22275(8) 0.0306(3) Uani 1 1 d .
C14 C 0.02172(8) 0.55848(13) 0.22618(8) 0.0302(3) Uani 1 1 d .
C15 C 0.09697(9) 0.35056(14) 0.28206(9) 0.0339(3) Uani 1 1 d .
C16 C 0.08908(10) 0.21948(15) 0.26807(11) 0.0448(4) Uani 1 1 d .
H16 H 0.0609 0.1891 0.2194 0.054 Uiso 1 1 calc R
C17 C 0.12366(13) 0.13374(18) 0.32749(14) 0.0597(5) Uani 1 1 d .
H17 H 0.1178 0.0462 0.3168 0.072 Uiso 1 1 calc R
C18 C 0.17095(14) 0.2953(2) 0.41121(11) 0.0642(6) Uani 1 1 d .
H18 H 0.1991 0.3229 0.4604 0.077 Uiso 1 1 calc R
C19 C 0.13869(11) 0.38735(17) 0.35633(9) 0.0460(4) Uani 1 1 d .
H19 H 0.1448 0.4741 0.3690 0.055 Uiso 1 1 calc R
C20 C 0.02981(11) 0.79470(16) 0.07810(10) 0.0466(4) Uani 1 1 d .
C21 C 0.03073(17) 0.7670(2) 0.00274(13) 0.0703(6) Uani 1 1 d .
H21A H 0.0870 0.7535 0.0106 0.105 Uiso 1 1 calc R
H21B H 0.0074 0.8389 -0.0301 0.105 Uiso 1 1 calc R
H21C H -0.0016 0.6914 -0.0192 0.105 Uiso 1 1 calc R
C22 C 0.09782(14) 0.89559(19) 0.11957(14) 0.0680(6) Uani 1 1 d .
H22A H 0.1002 0.9121 0.1677 0.102 Uiso 1 1 calc R
H22B H 0.0849 0.9739 0.0912 0.102 Uiso 1 1 calc R
H22C H 0.1507 0.8636 0.1256 0.102 Uiso 1 1 calc R
C23 C -0.05873(13) 0.8482(2) 0.05485(13) 0.0616(5) Uani 1 1 d .
H23A H -0.0991 0.7832 0.0283 0.092 Uiso 1 1 calc R
H23B H -0.0677 0.9218 0.0232 0.092 Uiso 1 1 calc R
H23C H -0.0644 0.8730 0.0986 0.092 Uiso 1 1 calc R
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C17 N1 C18 115.84(17) . .
C1 C1 C2 122.67(9) 2 .
C14 C2 C1 115.16(13) . .
C14 C2 C3 121.14(13) . .
C1 C2 C3 123.19(13) . .
C4 C3 C2 116.04(13) . .
C4 C3 C20 124.03(14) . .
C2 C3 C20 119.82(13) . .
C3 C4 C12 121.79(13) . .
C3 C4 C5 129.25(13) . .
C12 C4 C5 108.45(13) . .
C6 C5 C4 103.82(13) . .
C7 C6 C11 121.64(16) . .
C7 C6 C5 127.18(16) . .
C11 C6 C5 111.17(13) . .
C8 C7 C6 119.05(17) . .
C7 C8 C9 120.05(16) . .
C8 C9 C10 121.21(18) . .
C9 C10 C11 119.51(17) . .
C6 C11 C10 118.51(14) . .
C6 C11 C12 107.99(13) . .
C10 C11 C12 133.47(14) . .
C13 C12 C4 121.00(13) . .
C13 C12 C11 130.71(13) . .
C4 C12 C11 108.18(12) . .
C12 C13 C14 117.95(12) . .
C12 C13 C15 120.51(12) . .
C14 C13 C15 120.07(12) . .
C2 C14 C13 119.18(12) . .
C2 C14 C14 118.21(9) . 2
C13 C14 C14 122.36(9) . 2
C16 C15 C19 116.45(15) . .
C16 C15 C13 124.30(15) . .
C19 C15 C13 119.07(14) . .
C15 C16 C17 119.38(18) . .
N1 C17 C16 124.21(18) . .
N1 C18 C19 124.2(2) . .
C18 C19 C15 119.88(18) . .
C22 C20 C21 107.67(17) . .
C22 C20 C23 112.21(16) . .
C21 C20 C23 103.22(17) . .
C22 C20 C3 109.15(15) . .
C21 C20 C3 113.67(15) . .
C23 C20 C3 110.84(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C17 1.326(3) .
N1 C18 1.335(3) .
C1 C1 1.347(3) 2
C1 C2 1.437(2) .
C2 C14 1.4198(19) .
C2 C3 1.439(2) .
C3 C4 1.389(2) .
C3 C20 1.557(2) .
C4 C12 1.431(2) .
C4 C5 1.520(2) .
C5 C6 1.494(2) .
C6 C7 1.389(2) .
C6 C11 1.395(2) .
C7 C8 1.376(3) .
C8 C9 1.384(3) .
C9 C10 1.384(2) .
C10 C11 1.396(2) .
C11 C12 1.4919(19) .
C12 C13 1.3926(19) .
C13 C14 1.4246(18) .
C13 C15 1.4964(19) .
C14 C14 1.475(3) 2
C15 C16 1.386(2) .
C15 C19 1.388(2) .
C16 C17 1.392(3) .
C18 C19 1.376(3) .
C20 C22 1.542(3) .
C20 C21 1.542(3) .
C20 C23 1.547(3) .
