#------------------------------------------------------------------------------
#$Date: 2019-11-23 17:40:15 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234256 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/48/7124819.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_7124819
loop_
_publ_author_name
'Stephens, David E.'
'Lakey-Beitia, Johant'
'Burch, Jessica E.'
'Arman, Hadi D.'
'Larionov, Oleg V.'
_publ_section_title
;
 Mechanistic insights into the potassium tert-butoxide-mediated synthesis
 of N-heterobiaryls.
;
_journal_issue                   64
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9945
_journal_page_last               9948
_journal_paper_doi               10.1039/c6cc04816a
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C26 H28 N2'
_chemical_formula_sum            'C26 H28 N2'
_chemical_formula_weight         368.50
_chemical_name_systematic        '6,6'-Di-tert-butyl-2,2'-biquinoline '
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-08-05
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-04-14 deposited with the CCDC.
2016-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.032(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.301(11)
_cell_length_b                   6.133(3)
_cell_length_c                   18.738(11)
_cell_measurement_reflns_used    2763
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.4
_cell_volume                     2098(2)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
scan:
	Number of images: 246
	           Slice: -68.0000 - 55.0000
	     Image width: 0.5000
	        Exp time: 50.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 180.0000
	             XTD: 34.9591
	          2theta: -35.0597
scan:
	Number of images: 188
	           Slice: -50.0000 - 44.0000
	     Image width: 0.5000
	        Exp time: 50.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 0.0000
	             XTD: 34.9591
	          2theta: -35.0597
scan:
	Number of images: 94
	           Slice: -70.0000 - -23.0000
	     Image width: 0.5000
	        Exp time: 50.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 34.9591
	          2theta: -35.0597
scan:
	Number of images: 88
	           Slice: -56.0000 - -12.0000
	     Image width: 0.5000
	        Exp time: 50.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 270.0000
	             XTD: 34.9591
	          2theta: -35.0597
scan:
	Number of images: 62
	           Slice: -115.0000 - -84.0000
	     Image width: 0.5000
	        Exp time: 50.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 270.0000
	             XTD: 34.9591
	          2theta: -35.0597
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.050853
_diffrn_orient_matrix_UB_12      0.016597
_diffrn_orient_matrix_UB_13      -0.011794
_diffrn_orient_matrix_UB_21      0.059553
_diffrn_orient_matrix_UB_22      0.138756
_diffrn_orient_matrix_UB_23      -0.061512
_diffrn_orient_matrix_UB_31      0.000186
_diffrn_orient_matrix_UB_32      -0.021748
_diffrn_orient_matrix_UB_33      -0.048878
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0857
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6151
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.493
_diffrn_reflns_theta_min         3.008
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0634
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0200P)²+2.7500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1458
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1474
_reflns_number_total             1924
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cc04816a2.cif
_cod_data_source_block           cd1341f
_cod_database_code               7124819
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C3(H3), C2(H2)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
;
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'glass fiber'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
N1 N 0.33464(10) 0.3935(3) 0.26677(9) 0.0499(5) Uani 1 1 d .
C9 C 0.40081(11) 0.3710(4) 0.30424(10) 0.0462(5) Uani 1 1 d .
C1 C 0.28591(11) 0.2368(4) 0.27088(10) 0.0477(5) Uani 1 1 d .
C4 C 0.41890(11) 0.1856(4) 0.34739(10) 0.0469(5) Uani 1 1 d .
C5 C 0.48863(12) 0.1738(4) 0.38436(11) 0.0494(5) Uani 1 1 d .
H5 H 0.5001 0.0512 0.4121 0.059 Uiso 1 1 calc R
C6 C 0.54016(12) 0.3346(4) 0.38122(10) 0.0467(5) Uani 1 1 d .
C7 C 0.52033(13) 0.5187(4) 0.33790(12) 0.0544(6) Uani 1 1 d .
H7 H 0.5539 0.6317 0.3349 0.065 Uiso 1 1 calc R
C8 C 0.45378(13) 0.5352(4) 0.30067(12) 0.0552(6) Uani 1 1 d .
H8 H 0.4433 0.6575 0.2724 0.066 Uiso 1 1 calc R
C3 C 0.36529(13) 0.0217(4) 0.34948(12) 0.0579(6) Uani 1 1 d .
H3 H 0.3750 -0.1034 0.3766 0.070 Uiso 1 1 calc R
C10 C 0.61410(12) 0.3256(4) 0.42341(11) 0.0517(6) Uani 1 1 d .
C2 C 0.29971(13) 0.0451(4) 0.31228(12) 0.0569(6) Uani 1 1 d .
H2 H 0.2641 -0.0627 0.3138 0.068 Uiso 1 1 calc R
C12 C 0.60868(15) 0.4558(5) 0.49313(13) 0.0767(8) Uani 1 1 d .
H12A H 0.5946 0.6032 0.4818 0.115 Uiso 1 1 calc GR
H12B H 0.6554 0.4554 0.5199 0.115 Uiso 1 1 calc GR
H12C H 0.5727 0.3899 0.5212 0.115 Uiso 1 1 calc GR
C11 C 0.67446(14) 0.4263(5) 0.38093(16) 0.0765(8) Uani 1 1 d .
H11A H 0.6731 0.3618 0.3342 0.115 Uiso 1 1 calc GR
H11B H 0.7214 0.3995 0.4056 0.115 Uiso 1 1 calc GR
H11C H 0.6667 0.5807 0.3765 0.115 Uiso 1 1 calc GR
C13 C 0.63708(15) 0.0917(5) 0.44215(16) 0.0789(8) Uani 1 1 d .
H13A H 0.6029 0.0289 0.4728 0.118 Uiso 1 1 calc GR
H13B H 0.6851 0.0922 0.4663 0.118 Uiso 1 1 calc GR
H13C H 0.6377 0.0071 0.3991 0.118 Uiso 1 1 calc GR
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_3
C1 N1 C9 118.46(19) .
N1 C9 C4 122.5(2) .
N1 C9 C8 119.63(19) .
C8 C9 C4 117.9(2) .
N1 C1 C1 117.8(2) 7
N1 C1 C2 122.7(2) .
C2 C1 C1 119.5(3) 7
C5 C4 C9 119.1(2) .
C5 C4 C3 123.9(2) .
C3 C4 C9 116.9(2) .
C4 C5 H5 118.5 .
C6 C5 C4 123.0(2) .
C6 C5 H5 118.5 .
C5 C6 C7 116.6(2) .
C5 C6 C10 122.8(2) .
C7 C6 C10 120.5(2) .
C6 C7 H7 118.9 .
C8 C7 C6 122.2(2) .
C8 C7 H7 118.9 .
C9 C8 H8 119.4 .
C7 C8 C9 121.2(2) .
C7 C8 H8 119.4 .
C4 C3 H3 119.8 .
C2 C3 C4 120.3(2) .
C2 C3 H3 119.8 .
C6 C10 C12 108.32(18) .
C6 C10 C11 111.24(19) .
C6 C10 C13 112.0(2) .
C11 C10 C12 108.8(2) .
C13 C10 C12 108.9(2) .
C13 C10 C11 107.5(2) .
C1 C2 H2 120.4 .
C3 C2 C1 119.1(2) .
C3 C2 H2 120.4 .
C10 C12 H12A 109.5 .
C10 C12 H12B 109.5 .
C10 C12 H12C 109.5 .
H12A C12 H12B 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
C10 C11 H11A 109.5 .
C10 C11 H11B 109.5 .
C10 C11 H11C 109.5 .
H11A C11 H11B 109.5 .
H11A C11 H11C 109.5 .
H11B C11 H11C 109.5 .
C10 C13 H13A 109.5 .
C10 C13 H13B 109.5 .
C10 C13 H13C 109.5 .
H13A C13 H13B 109.5 .
H13A C13 H13C 109.5 .
H13B C13 H13C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C9 1.363(3) .
N1 C1 1.317(3) .
C9 C4 1.421(3) .
C9 C8 1.403(3) .
C1 C1 1.490(4) 7
C1 C2 1.421(3) .
C4 C5 1.410(3) .
C4 C3 1.407(3) .
C5 H5 0.9300 .
C5 C6 1.369(3) .
C6 C7 1.423(3) .
C6 C10 1.519(3) .
C7 H7 0.9300 .
C7 C8 1.364(3) .
C8 H8 0.9300 .
C3 H3 0.9300 .
C3 C2 1.352(3) .
C10 C12 1.540(3) .
C10 C11 1.536(3) .
C10 C13 1.529(4) .
C2 H2 0.9300 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N1 C9 C4 C5 179.77(18) . .
N1 C9 C4 C3 0.7(3) . .
N1 C9 C8 C7 179.5(2) . .
N1 C1 C2 C3 0.4(3) . .
C9 N1 C1 C1 -179.5(2) . 7
C9 N1 C1 C2 -0.5(3) . .
C9 C4 C5 C6 0.6(3) . .
C9 C4 C3 C2 -0.8(3) . .
C1 N1 C9 C4 -0.1(3) . .
C1 N1 C9 C8 179.84(19) . .
C1 C1 C2 C3 179.4(2) 7 .
C4 C9 C8 C7 -0.6(3) . .
C4 C5 C6 C7 -0.2(3) . .
C4 C5 C6 C10 177.52(19) . .
C4 C3 C2 C1 0.3(3) . .
C5 C4 C3 C2 -179.8(2) . .
C5 C6 C7 C8 -0.5(3) . .
C5 C6 C10 C12 -95.8(3) . .
C5 C6 C10 C11 144.6(2) . .
C5 C6 C10 C13 24.3(3) . .
C6 C7 C8 C9 1.0(3) . .
C7 C6 C10 C12 81.8(2) . .
C7 C6 C10 C11 -37.7(3) . .
C7 C6 C10 C13 -158.0(2) . .
C8 C9 C4 C5 -0.1(3) . .
C8 C9 C4 C3 -179.23(19) . .
C3 C4 C5 C6 179.6(2) . .
C10 C6 C7 C8 -178.3(2) . .
