#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:36:50 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180229 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/15/7111567.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_7111567
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            'C68 H56 Cl4 N6'
_chemical_formula_weight         1098.99
_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                 128.084(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   27.005(2)
_cell_length_b                   14.7364(12)
_cell_length_c                   17.7781(15)
_cell_measurement_reflns_used    8183
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.29
_cell_volume                     5568.7(8)
_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 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0494
_diffrn_reflns_av_sigmaI/netI    0.0812
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18930
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.29
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular fragment'
_exptl_crystal_F_000             2296
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         6323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0665
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1252P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1843
_refine_ls_wR_factor_ref         0.2032
_reflns_number_gt                3872
_reflns_number_total             6323
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b921667gsup1.cif
_cod_data_source_block           bw6plt
_cod_original_cell_volume        5568.6(8)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7111567
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 1.01724(7) 0.70953(11) 0.93604(10) 0.0486(4) Uani 1 1 d .
N2 N 1.07154(8) 0.91571(14) 1.07469(13) 0.0678(5) Uani 1 1 d .
N3 N 0.93135(8) 0.55579(12) 0.73590(12) 0.0608(4) Uani 1 1 d .
C1 C 0.92915(7) 0.90611(12) 0.70898(11) 0.0411(4) Uani 1 1 d .
C2 C 0.86412(7) 0.91147(12) 0.63704(12) 0.0438(4) Uani 1 1 d .
C3 C 0.81229(7) 0.85825(13) 0.62194(12) 0.0481(4) Uani 1 1 d .
C4 C 0.80946(9) 0.79551(15) 0.67721(15) 0.0564(5) Uani 1 1 d .
H4 H 0.8459 0.7783 0.7366 0.068 Uiso 1 1 calc R
C5 C 0.75142(10) 0.75838(18) 0.64292(18) 0.0692(6) Uani 1 1 d .
H5 H 0.7491 0.7170 0.6802 0.083 Uiso 1 1 calc R
C6 C 0.69735(10) 0.7826(2) 0.55393(19) 0.0767(7) Uani 1 1 d .
H6 H 0.6594 0.7551 0.5307 0.092 Uiso 1 1 calc R
C7 C 0.69887(9) 0.84697(18) 0.49923(17) 0.0694(6) Uani 1 1 d .
H7 H 0.6622 0.8642 0.4402 0.083 Uiso 1 1 calc R
C8 C 0.75625(8) 0.88568(15) 0.53383(14) 0.0551(5) Uani 1 1 d .
C9 C 0.76868(8) 0.95834(16) 0.48926(14) 0.0597(5) Uani 1 1 d .
H9A H 0.7434 1.0117 0.4759 0.072 Uiso 1 1 calc R
H9B H 0.7597 0.9373 0.4303 0.072 Uiso 1 1 calc R
C10 C 0.83859(8) 0.97883(13) 0.56432(12) 0.0481(4) Uani 1 1 d .
C11 C 0.87357(8) 1.05362(14) 0.57307(14) 0.0515(5) Uani 1 1 d .
C12 C 0.93654(8) 1.05879(13) 0.66085(14) 0.0487(4) Uani 1 1 d .
C13 C 0.96549(7) 0.97890(12) 0.71543(12) 0.0430(4) Uani 1 1 d .
C14 C 0.97218(10) 1.14056(14) 0.70591(16) 0.0599(5) Uani 1 1 d .
H14 H 0.9562 1.1952 0.6730 0.072 Uiso 1 1 calc R
C15 C 0.95893(7) 0.83638(12) 0.78645(11) 0.0415(4) Uani 1 1 d .
C16 C 0.99652(7) 0.86367(13) 0.88190(12) 0.0447(4) Uani 1 1 d .
H16 H 1.0025 0.9250 0.8974 0.054 Uiso 1 1 calc R
C17 C 1.02504(7) 0.79852(13) 0.95380(12) 0.0459(4) Uani 1 1 d .
C18 C 0.98028(8) 0.68216(13) 0.84392(12) 0.0456(4) Uani 1 1 d .
C19 C 0.95079(7) 0.74371(12) 0.76782(12) 0.0431(4) Uani 1 1 d .
H19 H 0.9259 0.7228 0.7051 0.052 Uiso 1 1 calc R
C20 C 0.84794(10) 1.12796(17) 0.49610(17) 0.0679(6) Uani 1 1 d .
C21 C 0.82090(17) 1.2065(2) 0.5183(3) 0.1100(12) Uani 1 1 d .
H21A H 0.7873 1.1841 0.5178 0.165 Uiso 1 1 calc R
H21B H 0.8051 1.2530 0.4708 0.165 Uiso 1 1 calc R
H21C H 0.8535 1.2311 0.5802 0.165 Uiso 1 1 calc R
C22 C 0.79639(14) 1.0926(3) 0.3955(2) 0.1023(11) Uani 1 1 d .
H22A H 0.8102 1.0374 0.3850 0.153 Uiso 1 1 calc R
H22B H 0.7877 1.1372 0.3494 0.153 Uiso 1 1 calc R
H22C H 0.7589 1.0811 0.3890 0.153 Uiso 1 1 calc R
C23 C 0.90008(13) 1.1623(2) 0.4906(2) 0.0851(8) Uani 1 1 d .
H23A H 0.9325 1.1920 0.5494 0.128 Uiso 1 1 calc R
H23B H 0.8822 1.2045 0.4387 0.128 Uiso 1 1 calc R
H23C H 0.9177 1.1118 0.4804 0.128 Uiso 1 1 calc R
C24 C 1.06691(8) 0.82666(14) 1.05650(12) 0.0493(4) Uani 1 1 d .
C25 C 1.10080(10) 0.76301(18) 1.12878(14) 0.0654(6) Uani 1 1 d .
H25 H 1.0973 0.7014 1.1148 0.078 Uiso 1 1 calc R
C26 C 1.14027(12) 0.7936(2) 1.22278(17) 0.0830(8) Uani 1 1 d .
H26 H 1.1641 0.7523 1.2726 0.100 Uiso 1 1 calc R
C27 C 1.14393(11) 0.8829(2) 1.24156(16) 0.0779(7) Uani 1 1 d .
H27 H 1.1693 0.9042 1.3041 0.093 Uiso 1 1 calc R
C28 C 1.10935(11) 0.9412(2) 1.16632(17) 0.0758(7) Uani 1 1 d .
H28 H 1.1123 1.0029 1.1797 0.091 Uiso 1 1 calc R
C29 C 0.97233(9) 0.58293(13) 0.82724(13) 0.0503(4) Uani 1 1 d .
C30 C 1.00530(12) 0.52145(15) 0.90213(17) 0.0660(6) Uani 1 1 d .
H30 H 1.0335 0.5422 0.9647 0.079 Uiso 1 1 calc R
C31 C 0.99634(14) 0.42973(16) 0.8839(2) 0.0794(7) Uani 1 1 d .
H31 H 1.0180 0.3878 0.9335 0.095 Uiso 1 1 calc R
C32 C 0.95439(14) 0.40160(17) 0.7900(2) 0.0807(7) Uani 1 1 d .
H32 H 0.9471 0.3402 0.7748 0.097 Uiso 1 1 calc R
C33 C 0.92383(13) 0.46641(17) 0.71994(18) 0.0727(6) Uani 1 1 d .
H33 H 0.8959 0.4468 0.6569 0.087 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C17 N1 C18 118.10(15) . .
C28 N2 C24 117.2(2) . .
C33 N3 C29 117.01(19) . .
C2 C1 C13 116.74(15) . .
C2 C1 C15 122.69(15) . .
C13 C1 C15 119.75(14) . .
C1 C2 C10 120.05(16) . .
C1 C2 C3 130.61(16) . .
C10 C2 C3 109.31(14) . .
C4 C3 C8 119.28(17) . .
C4 C3 C2 133.31(16) . .
C8 C3 C2 107.30(17) . .
C3 C4 C5 119.35(19) . .
C6 C5 C4 120.5(2) . .
C7 C6 C5 121.0(2) . .
C6 C7 C8 118.8(2) . .
C7 C8 C3 121.0(2) . .
C7 C8 C9 128.03(18) . .
C3 C8 C9 110.99(16) . .
C8 C9 C10 103.91(15) . .
C11 C10 C2 122.21(15) . .
C11 C10 C9 129.84(17) . .
C2 C10 C9 107.50(16) . .
C10 C11 C12 115.44(17) . .
C10 C11 C20 123.96(17) . .
C12 C11 C20 120.60(18) . .
C13 C12 C11 118.97(17) . .
C13 C12 C14 114.72(16) . .
C11 C12 C14 125.95(17) . .
C1 C13 C12 120.97(14) . .
C1 C13 C13 121.89(12) . 2_756
C12 C13 C13 116.93(12) . 2_756
C14 C14 C12 122.12(12) 2_756 .
C19 C15 C16 117.53(16) . .
C19 C15 C1 122.66(15) . .
C16 C15 C1 119.81(16) . .
C17 C16 C15 119.60(17) . .
N1 C17 C16 122.93(16) . .
N1 C17 C24 116.83(16) . .
C16 C17 C24 120.24(17) . .
N1 C18 C19 122.20(17) . .
N1 C18 C29 116.43(16) . .
C19 C18 C29 121.37(16) . .
C15 C19 C18 119.62(16) . .
C22 C20 C11 112.5(2) . .
C22 C20 C21 108.8(2) . .
C11 C20 C21 109.2(2) . .
C22 C20 C23 104.1(2) . .
C11 C20 C23 111.01(17) . .
C21 C20 C23 111.2(2) . .
N2 C24 C25 122.00(18) . .
N2 C24 C17 117.02(17) . .
C25 C24 C17 120.94(19) . .
C24 C25 C26 118.3(2) . .
C27 C26 C25 119.9(2) . .
C26 C27 C28 118.2(2) . .
N2 C28 C27 124.4(3) . .
N3 C29 C30 121.88(19) . .
N3 C29 C18 116.46(17) . .
C30 C29 C18 121.65(18) . .
C31 C30 C29 120.0(2) . .
C30 C31 C32 118.2(2) . .
C33 C32 C31 118.3(2) . .
N3 C33 C32 124.5(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C17 1.335(2) .
N1 C18 1.351(2) .
N2 C28 1.336(3) .
N2 C24 1.339(3) .
N3 C33 1.336(3) .
N3 C29 1.343(3) .
C1 C2 1.398(2) .
C1 C13 1.410(2) .
C1 C15 1.494(2) .
C2 C10 1.426(3) .
C2 C3 1.478(2) .
C3 C4 1.385(3) .
C3 C8 1.408(2) .
C4 C5 1.396(3) .
C5 C6 1.383(3) .
C6 C7 1.377(4) .
C7 C8 1.389(3) .
C8 C9 1.488(3) .
C9 C10 1.526(2) .
C10 C11 1.396(3) .
C11 C12 1.435(2) .
C11 C20 1.544(3) .
C12 C13 1.415(3) .
C12 C14 1.438(3) .
C13 C13 1.469(3) 2_756
C14 C14 1.345(4) 2_756
C15 C19 1.390(3) .
C15 C16 1.395(2) .
C16 C17 1.391(3) .
C17 C24 1.496(2) .
C18 C19 1.399(3) .
C18 C29 1.481(3) .
C20 C22 1.528(4) .
C20 C21 1.544(4) .
C20 C23 1.555(4) .
C24 C25 1.385(3) .
C25 C26 1.391(3) .
C26 C27 1.347(4) .
C27 C28 1.363(4) .
C29 C30 1.387(3) .
C30 C31 1.376(3) .
C31 C32 1.382(4) .
C32 C33 1.370(4) .
