#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:36:50 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180229 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/15/7111565.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_7111565
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           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 100.7890(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.4736(7)
_cell_length_b                   5.9821(3)
_cell_length_c                   24.7092(14)
_cell_measurement_reflns_used    5737
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.57
_cell_volume                     1811.17(17)
_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 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0692
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            11727
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.74
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular fragment'
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4067
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0568
_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)+(0.0799P)²+0.2633P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1552
_refine_ls_wR_factor_ref         0.1768
_reflns_number_gt                2850
_reflns_number_total             4067
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b921667gsup1.cif
_cod_data_source_block           bw4ccd
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7111565
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.14292(16) 0.3341(3) -0.07769(7) 0.0751(5) Uani 1 1 d .
C1 C 0.55243(14) 1.1012(3) -0.03772(7) 0.0539(4) Uani 1 1 d .
H1 H 0.5885 1.1711 -0.0628 0.065 Uiso 1 1 calc R
C2 C 0.55860(14) 1.1931(3) 0.01455(7) 0.0538(4) Uani 1 1 d .
H2 H 0.5983 1.3237 0.0237 0.065 Uiso 1 1 calc R
C3 C 0.50672(13) 1.0937(3) 0.05319(7) 0.0476(4) Uani 1 1 d .
C4 C 0.51661(13) 1.1938(3) 0.11070(7) 0.0477(4) Uani 1 1 d .
H4 H 0.5324 1.3531 0.1072 0.057 Uiso 1 1 calc R
C5 C 0.61256(13) 1.0968(3) 0.15476(7) 0.0530(4) Uani 1 1 d .
C6 C 0.60086(19) 0.8432(3) 0.16023(10) 0.0776(6) Uani 1 1 d .
H6A H 0.6072 0.7726 0.1261 0.116 Uiso 1 1 calc R
H6B H 0.5308 0.8095 0.1689 0.116 Uiso 1 1 calc R
H6C H 0.6572 0.7887 0.1891 0.116 Uiso 1 1 calc R
C7 C 0.72109(16) 1.1509(4) 0.13786(10) 0.0814(7) Uani 1 1 d .
H7A H 0.7287 1.3100 0.1352 0.122 Uiso 1 1 calc R
H7B H 0.7231 1.0839 0.1028 0.122 Uiso 1 1 calc R
H7C H 0.7798 1.0928 0.1649 0.122 Uiso 1 1 calc R
C8 C 0.61043(17) 1.2062(4) 0.21048(8) 0.0724(6) Uani 1 1 d .
H8A H 0.6710 1.1530 0.2372 0.109 Uiso 1 1 calc R
H8B H 0.5435 1.1687 0.2221 0.109 Uiso 1 1 calc R
H8C H 0.6155 1.3655 0.2071 0.109 Uiso 1 1 calc R
C9 C 0.41199(13) 1.1818(3) 0.12991(7) 0.0501(4) Uani 1 1 d .
C10 C 0.32696(13) 1.1754(3) 0.14508(6) 0.0502(4) Uani 1 1 d .
C11 C 0.22616(12) 1.1725(3) 0.16534(6) 0.0476(4) Uani 1 1 d .
C12 C 0.21211(14) 1.3138(3) 0.20819(7) 0.0597(5) Uani 1 1 d .
H12 H 0.2672 1.4137 0.2227 0.072 Uiso 1 1 calc R
C13 C 0.11746(15) 1.3076(3) 0.22943(8) 0.0654(5) Uani 1 1 d .
H13 H 0.1091 1.4031 0.2580 0.078 Uiso 1 1 calc R
C14 C 0.03547(15) 1.1608(3) 0.20850(8) 0.0635(5) Uani 1 1 d .
H14 H -0.0276 1.1555 0.2235 0.076 Uiso 1 1 calc R
C15 C 0.04609(14) 1.0216(3) 0.16545(8) 0.0597(5) Uani 1 1 d .
H15 H -0.0102 0.9241 0.1512 0.072 Uiso 1 1 calc R
C16 C 0.14106(13) 1.0260(3) 0.14310(7) 0.0497(4) Uani 1 1 d .
C17 C 0.14986(14) 0.8852(3) 0.09716(7) 0.0553(4) Uani 1 1 d .
C18 C 0.15214(14) 0.7700(3) 0.05811(7) 0.0571(4) Uani 1 1 d .
C19 C 0.15105(13) 0.6258(3) 0.01152(7) 0.0508(4) Uani 1 1 d .
C20 C 0.08318(16) 0.6656(3) -0.03821(8) 0.0609(5) Uani 1 1 d .
H20 H 0.0388 0.7917 -0.0431 0.073 Uiso 1 1 calc R
C21 C 0.08185(18) 0.5160(3) -0.08070(8) 0.0708(5) Uani 1 1 d .
H21 H 0.0347 0.5449 -0.1138 0.085 Uiso 1 1 calc R
C22 C 0.2086(2) 0.2995(3) -0.02995(10) 0.0790(6) Uani 1 1 d .
H22 H 0.2531 0.1736 -0.0267 0.095 Uiso 1 1 calc R
C23 C 0.21591(18) 0.4361(3) 0.01528(8) 0.0686(5) Uani 1 1 d .
H23 H 0.2636 0.4019 0.0479 0.082 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
C22 N1 C21 115.69(17) . .
C2 C1 C3 121.27(15) . 3_675
C3 C2 C1 121.23(15) . .
C2 C3 C1 117.50(15) . 3_675
C2 C3 C4 120.49(14) . .
C1 C3 C4 122.00(14) 3_675 .
C9 C4 C3 111.06(13) . .
C9 C4 C5 111.41(13) . .
C3 C4 C5 114.76(13) . .
C7 C5 C8 108.77(16) . .
C7 C5 C6 109.79(17) . .
C8 C5 C6 109.04(17) . .
C7 C5 C4 109.40(15) . .
C8 C5 C4 109.05(14) . .
C6 C5 C4 110.75(15) . .
C10 C9 C4 178.95(19) . .
C9 C10 C11 177.72(18) . .
C12 C11 C16 118.86(14) . .
C12 C11 C10 120.04(15) . .
C16 C11 C10 121.10(14) . .
C13 C12 C11 120.78(16) . .
C14 C13 C12 120.28(16) . .
C13 C14 C15 120.34(16) . .
C14 C15 C16 120.34(16) . .
C15 C16 C11 119.38(15) . .
C15 C16 C17 119.86(15) . .
C11 C16 C17 120.74(14) . .
C18 C17 C16 176.95(19) . .
C17 C18 C19 177.58(18) . .
C20 C19 C23 117.06(16) . .
C20 C19 C18 121.59(16) . .
C23 C19 C18 121.32(17) . .
C19 C20 C21 119.08(17) . .
N1 C21 C20 124.56(19) . .
N1 C22 C23 124.71(19) . .
C22 C23 C19 118.89(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C22 1.320(3) .
N1 C21 1.322(3) .
C1 C2 1.393(2) .
C1 C3 1.394(2) 3_675
C2 C3 1.384(2) .
C3 C1 1.394(2) 3_675
C3 C4 1.526(2) .
C4 C9 1.471(2) .
C4 C5 1.571(2) .
C5 C7 1.524(2) .
C5 C8 1.529(2) .
C5 C6 1.532(3) .
C9 C10 1.190(2) .
C10 C11 1.438(2) .
C11 C12 1.392(2) .
C11 C16 1.407(2) .
C12 C13 1.379(2) .
C13 C14 1.373(3) .
C14 C15 1.377(2) .
C15 C16 1.398(2) .
C16 C17 1.434(2) .
C17 C18 1.190(2) .
C18 C19 1.437(2) .
C19 C20 1.376(3) .
C19 C23 1.387(2) .
C20 C21 1.377(3) .
C22 C23 1.374(3) .
