#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/31/7213138.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_7213138
loop_
_publ_author_name
'Tsue, Hirohito'
'Fujinami, Hideyuki'
'Itakura, Takeshi'
'Tsuchiya, Ryuta'
'Kobayashi, Kimiko'
'Takahashi, Hiroki'
'Hirao, Ken-ichi'
_publ_section_title
;
 8,8′-Dialkyl-1,1′-biisoquinolines: preparation, absolute
 configuration and unexpected racemization behaviour †
;
_journal_issue                   24
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              3677
_journal_paper_doi               10.1039/a905161i
_journal_year                    1999
_chemical_formula_moiety         'C20 H16 N2 '
_chemical_formula_sum            'C20 H16 N2'
_chemical_formula_weight         284.35
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_Int_Tables_number      148
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_audit_creation_date             'Oct 11 11996'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   31.695(2)
_cell_length_b                   31.695(2)
_cell_length_c                   7.7985(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296.7
_cell_measurement_theta_max      18.34
_cell_measurement_theta_min      10.55
_cell_volume                     6784.6(9)
_computing_cell_refinement       'CAD4 express'
_computing_data_collection       'CAD4 express'
_computing_data_reduction        'UNICS III'
_computing_publication_material  'UNICS III'
_computing_structure_refinement  'The Block diagonal least squer'
_computing_structure_solution    MULTAN78
_diffrn_ambient_temperature      293
_diffrn_measurement_device_type  'Enraf nonius CAD4'
_diffrn_measurement_method       ω
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'CAD4 sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3053
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         25.75
_diffrn_reflns_theta_min         2
_diffrn_standards_decay_%        -2.40
_diffrn_standards_interval_count 120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   Tompa_analytical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2700
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.430
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.17
_refine_ls_goodness_of_fit_all   2.10
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           block
_refine_ls_number_constraints    0
_refine_ls_number_parameters     264
_refine_ls_number_reflns         2215
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          1.36
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00078|Fo|²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0410
_refine_ls_wR_factor_ref         0.0410
_reflns_number_gt                2215
_reflns_number_total             2355
_reflns_observed_criterion       >2.0sigma(I)
_cod_data_source_file            905161isup1.cif
_cod_data_source_block           1
_cod_original_cell_volume        6784.7(8)
_cod_original_sg_symbol_H-M      'R_-3 '
_cod_original_formula_sum        'C20 H16 N2 '
_cod_database_code               7213138
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-y,x-y,z
-x+y,-x,z
-x,-y,-z
y,-x+y,-z
x-y,x,-z
2/3+x,1/3+y,1/3+z
2/3-y,1/3+x-y,1/3+z
2/3-x+y,1/3-x,1/3+z
2/3-x,1/3-y,1/3-z
2/3+y,1/3-x+y,1/3-z
2/3+x-y,1/3+x,1/3-z
1/3+x,2/3+y,2/3+z
1/3-y,2/3+x-y,2/3+z
1/3-x+y,2/3-x,2/3+z
1/3-x,2/3-y,2/3-z
1/3+y,2/3-x+y,2/3-z
1/3+x-y,2/3+x,2/3-z
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_calc_flag
N(2) N 0.2133(1) 0.2273(1) 0.2675(2) 0.042(1) Uani 1.00 d
N(12) N 0.2678(1) 0.1685(1) 0.2369(3) 0.046(1) Uani 1.00 d
C(1) C 0.2235(1) 0.2049(1) 0.1454(3) 0.033(1) Uani 1.00 d
C(3) C 0.2185(1) 0.2719(1) 0.2315(3) 0.048(1) Uani 1.00 d
C(4) C 0.2357(1) 0.2951(1) 0.0798(3) 0.043(1) Uani 1.00 d
C(5) C 0.2667(1) 0.2961(1) -0.2107(3) 0.045(1) Uani 1.00 d
C(6) C 0.2759(1) 0.2729(1) -0.3380(3) 0.050(1) Uani 1.00 d
C(7) C 0.2646(1) 0.2243(1) -0.3159(3) 0.048(1) Uani 1.00 d
C(8) C 0.2467(1) 0.1994(1) -0.1641(3) 0.038(1) Uani 1.00 d
C(9) C 0.2391(1) 0.2241(1) -0.0236(3) 0.031(1) Uani 1.00 d
C(10) C 0.2473(1) 0.2720(1) -0.0516(3) 0.036(1) Uani 1.00 d
C(11) C 0.2230(1) 0.1599(1) 0.2102(3) 0.033(1) Uani 1.00 d
C(13) C 0.2739(1) 0.1326(1) 0.3098(4) 0.053(1) Uani 1.00 d
C(14) C 0.2359(1) 0.0891(1) 0.3591(3) 0.048(1) Uani 1.00 d
C(15) C 0.1479(1) 0.0325(1) 0.3748(3) 0.052(1) Uani 1.00 d
C(16) C 0.1020(1) 0.0221(1) 0.3371(4) 0.059(1) Uani 1.00 d
C(17) C 0.0938(1) 0.0567(1) 0.2546(3) 0.051(1) Uani 1.00 d
C(18) C 0.1311(1) 0.1026(1) 0.2102(3) 0.037(1) Uani 1.00 d
C(19) C 0.1801(1) 0.1147(1) 0.2495(2) 0.032(1) Uani 1.00 d
C(20) C 0.1880(1) 0.0787(1) 0.3294(3) 0.038(1) Uani 1.00 d
C(21) C 0.2337(1) 0.1466(1) -0.1576(3) 0.058(1) Uani 1.00 d
C(22) C 0.1181(1) 0.1369(1) 0.1239(3) 0.052(1) Uani 1.00 d
H(3) H 0.215(1) 0.291(1) 0.334(4) 0.080(8) Uiso 1.00 calc
H(4) H 0.242(1) 0.330(1) 0.056(3) 0.073(7) Uiso 1.00 calc
H(5) H 0.270(1) 0.331(1) -0.223(3) 0.073(7) Uiso 1.00 calc
H(6) H 0.291(1) 0.290(1) -0.457(3) 0.079(8) Uiso 1.00 calc
H(7) H 0.270(1) 0.207(1) -0.420(3) 0.076(7) Uiso 1.00 calc
H(13) H 0.309(1) 0.137(1) 0.307(4) 0.087(8) Uiso 1.00 calc
H(14) H 0.242(1) 0.059(1) 0.403(3) 0.080(8) Uiso 1.00 calc
H(15) H 0.156(1) 0.005(1) 0.436(3) 0.083(8) Uiso 1.00 calc
H(16) H 0.071(1) -0.013(1) 0.377(4) 0.085(8) Uiso 1.00 calc
H(17) H 0.057(1) 0.051(1) 0.218(4) 0.083(8) Uiso 1.00 calc
H(21)1 H 0.256(1) 0.142(1) -0.088(3) 0.082(8) Uiso 1.00 calc
H(21)2 H 0.200(1) 0.126(1) -0.111(3) 0.083(8) Uiso 1.00 calc
H(21)3 H 0.234(1) 0.133(1) -0.271(3) 0.083(8) Uiso 1.00 calc
H(22)1 H 0.135(1) 0.150(1) 0.002(3) 0.076(7) Uiso 1.00 calc
H(22)2 H 0.081(1) 0.120(1) 0.092(3) 0.078(7) Uiso 1.00 calc
H(22)3 H 0.125(1) 0.165(1) 0.205(3) 0.080(8) Uiso 1.00 calc
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(1) N(2) C(3) 118.2(2)
C(11) N(12) C(13) 118.7(2)
N(2) C(1) C(9) 124.1(2)
N(2) C(1) C(11) 112.1(2)
C(9) C(1) C(11) 123.3(2)
N(2) C(3) C(4) 123.2(3)
N(2) C(3) H(3) 116.6(17)
C(4) C(3) H(3) 119.2(16)
C(3) C(4) C(10) 119.4(3)
C(3) C(4) H(4) 122.7(15)
C(10) C(4) H(4) 117.8(15)
C(6) C(5) C(10) 120.0(2)
C(6) C(5) H(5) 124.0(15)
C(10) C(5) H(5) 115.8(15)
C(5) C(6) C(7) 120.1(2)
C(5) C(6) H(6) 122.3(19)
C(7) C(6) H(6) 117.7(19)
C(6) C(7) C(8) 122.6(2)
C(6) C(7) H(7) 117.5(16)
C(8) C(7) H(7) 120.0(16)
C(7) C(8) C(9) 118.6(2)
C(7) C(8) C(21) 118.0(2)
C(9) C(8) C(21) 123.4(2)
C(1) C(9) C(8) 126.1(2)
C(1) C(9) C(10) 115.7(2)
C(8) C(9) C(10) 118.2(2)
C(4) C(10) C(5) 120.6(2)
C(4) C(10) C(9) 119.1(2)
C(5) C(10) C(9) 120.3(2)
N(12) C(11) C(1) 110.9(2)
N(12) C(11) C(19) 123.8(2)
C(1) C(11) C(19) 125.2(2)
N(12) C(13) C(14) 122.6(3)
N(12) C(13) H(13) 117.0(17)
C(14) C(13) H(13) 119.6(17)
C(13) C(14) C(20) 119.8(3)
C(13) C(14) H(14) 121.1(14)
C(20) C(14) H(14) 118.3(13)
C(16) C(15) C(20) 119.5(3)
C(16) C(15) H(15) 122.6(13)
C(20) C(15) H(15) 117.8(13)
C(15) C(16) C(17) 120.5(2)
C(15) C(16) H(16) 119.6(20)
C(17) C(16) H(16) 119.8(20)
C(16) C(17) C(18) 122.6(3)
C(16) C(17) H(17) 124.4(15)
C(18) C(17) H(17) 113.0(15)
C(17) C(18) C(19) 118.1(3)
C(17) C(18) C(22) 118.1(2)
C(19) C(18) C(22) 123.7(2)
C(11) C(19) C(18) 125.6(2)
C(11) C(19) C(20) 115.8(2)
C(18) C(19) C(20) 118.6(2)
C(14) C(20) C(15) 120.3(3)
C(14) C(20) C(19) 119.2(2)
C(15) C(20) C(19) 120.5(3)
C(8) C(21) H(21)1 111.7(16)
C(8) C(21) H(21)2 110.5(21)
C(8) C(21) H(21)3 112.5(18)
H(21)1 C(21) H(21)2 109.3(24)
H(21)1 C(21) H(21)3 107.0(30)
H(21)2 C(21) H(21)3 105.6(21)
C(18) C(22) H(22)1 114.8(21)
C(18) C(22) H(22)2 111.8(18)
C(18) C(22) H(22)3 109.4(19)
H(22)1 C(22) H(22)2 101.6(21)
H(22)1 C(22) H(22)3 111.1(21)
H(22)2 C(22) H(22)3 107.7(26)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N(2) C(1) 1.320(3)
N(2) C(3) 1.368(4)
N(12) C(11) 1.322(3)
N(12) C(13) 1.370(42
C(1) C(9) 1.432(3)
C(1) C(11) 1.504(35
C(3) C(4) 1.355(3)
C(3) H(3) 1.045(32)
C(4) C(10) 1.411(4)
C(4) H(4) 1.058(32)
C(5) C(6) 1.351(4)
C(5) C(10) 1.426(3)
C(5) H(5) 1.049(33)
C(6) C(7) 1.407(4)
C(6) H(6) 1.056(26)
C(7) C(8) 1.377(3)
C(7) H(7) 1.036(31)
C(8) C(9) 1.435(3)
C(8) C(21) 1.510(4)
C(9) C(10) 1.424(3)
C(11) C(19) 1.432(2)
C(13) C(14) 1.357(3)
C(13) H(13) 1.047(35)
C(14) C(20) 1.405(4)
C(14) H(14) 1.094(36)
C(15) C(16) 1.354(5)
C(15) C(20) 1.423(3)
C(15) H(15) 1.135(37)
C(16) C(17) 1.404(5)
C(16) H(16) 1.090(24)
C(17) C(18) 1.383(3)
C(17) H(17) 1.107(34)
C(18) C(19) 1.432(3)
C(18) C(22) 1.504(4)
C(19) C(20) 1.427(4)
C(21) H(21)1 0.960(34)
C(21) H(21)2 1.001(26)
C(21) H(21)3 0.980(29)
C(22) H(22)1 1.063(26)
C(22) H(22)2 1.041(28)
C(22) H(22)3 1.019(30)
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
C(3) N(2) C(1) C(9) -0.9(3)
C(3) N(2) C(1) C(11) 171.9(2)
C(1) N(2) C(3) C(4) -3.1(4)
C(13) N(12) C(11) C(1) 174.6(2)
C(13) N(12) C(11) C(19) -1.5(4)
C(11) N(12) C(13) C(14) -1.5(4)
N(2) C(1) C(9) C(8) -174.5(2)
N(2) C(1) C(9) C(10) 5.0(3)
C(11) C(1) C(9) C(8) 13.4(3)
C(11) C(1) C(9) C(10) -167.0(2)
N(2) C(1) C(11) N(12) -101.2(2)
N(2) C(1) C(11) C(19) 74.8(3)
C(9) C(1) C(11) N(12) 71.7(3)
C(9) C(1) C(11) C(19) -112.3(3)
N(2) C(3) C(4) C(10) 2.5(4)
C(3) C(4) C(10) C(5) -178.2(2)
C(3) C(4) C(10) C(9) 2.0(4)
C(10) C(5) C(6) C(7) 2.2(4)
C(6) C(5) C(10) C(4) -177.4(2)
C(6) C(5) C(10) C(9) 2.5(4)
C(5) C(6) C(7) C(8) -3.6(4)
C(6) C(7) C(8) C(9) 0.2(4)
C(6) C(7) C(8) C(21) 177.2(3)
C(7) C(8) C(9) C(1) -176.2(2)
C(7) C(8) C(9) C(10) 4.3(3)
C(21) C(8) C(9) C(1) 7.0(4)
C(21) C(8) C(9) C(10) -172.5(2)
C(1) C(9) C(10) C(4) -5.4(3)
C(1) C(9) C(10) C(5) 174.8(2)
C(8) C(9) C(10) C(4) 174.2(2)
C(8) C(9) C(10) C(5) -5.7(3)
N(12) C(11) C(19) C(18) -174.7(2)
N(12) C(11) C(19) C(20) 3.0(3)
C(1) C(11) C(19) C(18) 9.8(4)
C(1) C(11) C(19) C(20) -172.5(2)
N(12) C(13) C(14) C(20) 2.6(4)
C(13) C(14) C(20) C(15) 177.7(3)
C(13) C(14) C(20) C(19) -0.9(4)
C(20) C(15) C(16) C(17) -0.3(4)
C(16) C(15) C(20) C(14) -176.6(3)
C(16) C(15) C(20) C(19) 2.0(4)
C(15) C(16) C(17) C(18) -1.0(4)
C(16) C(17) C(18) C(19) 0.5(4)
C(16) C(17) C(18) C(22) -179.3(3)
C(17) C(18) C(19) C(11) 178.8(2)
C(17) C(18) C(19) C(20) 1.2(3)
C(22) C(18) C(19) C(11) -1.3(4)
C(22) C(18) C(19) C(20) -179.0(2)
C(11) C(19) C(20) C(14) -1.7(3)
C(11) C(19) C(20) C(15) 179.7(2)
C(18) C(19) C(20) C(14) 176.1(2)
C(18) C(19) C(20) C(15) -2.4(3)
