#------------------------------------------------------------------------------
#$Date: 2020-08-14 02:05:52 +0300 (Fri, 14 Aug 2020) $
#$Revision: 255298 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/86/4038692.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_4038692
loop_
_publ_author_name
'Rowlands, Gareth J.'
'Severinsen, Rebecca J.'
'Buchanan, Jenna K.'
'Shaffer, Karl J.'
'Jameson, Heather T.'
'Thennakoon, Nishani'
'Leito, Ivo'
'Lõkov, Märt'
'Kütt, Agnes'
'Vianello, Robert'
'Despotović, Ines'
'Radić, Nena'
'Plieger, Paul G.'
_publ_section_title
;
 Synthesis and Basicity Studies of Quinolino[7,8-h]quinoline Derivatives
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01428
_journal_year                    2020
_chemical_formula_moiety         'C26 H16 N4'
_chemical_formula_sum            'C26 H16 N4'
_chemical_formula_weight         384.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2bc 2ab'
_space_group_name_H-M_alt        'P b n b'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-10-13
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7745(4)
_cell_length_b                   14.5862(7)
_cell_length_c                   16.6756(12)
_cell_measurement_reflns_used    3365
_cell_measurement_temperature    163
_cell_measurement_theta_max      70.2
_cell_measurement_theta_min      6.6
_cell_volume                     1891.02(19)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      163
_diffrn_detector                 RX
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
scan:
	Number of images: 72
	           Slice: 20.0000 - 200.0000
	     Image width: 2.5000
	        Exp time: 120.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 180.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 68
	           Slice: 21.0000 - 191.0000
	     Image width: 2.5000
	        Exp time: 120.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 56
	           Slice: 55.0000 - 195.0000
	     Image width: 2.5000
	        Exp time: 120.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 42
	           Slice: 46.0000 - 151.0000
	     Image width: 2.5000
	        Exp time: 120.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 270.0000
	             XTD: 127.4000
	          2theta: 0.0000
;
_diffrn_measurement_device
;
Crystal Goniometer
;
_diffrn_measurement_device_type
;
Rigaku RAXIS conversion
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       FS_PROCESS
_diffrn_orient_matrix_UB_11      -0.039794
_diffrn_orient_matrix_UB_12      0.003191
_diffrn_orient_matrix_UB_13      -0.056957
_diffrn_orient_matrix_UB_21      0.018243
_diffrn_orient_matrix_UB_22      -0.067555
_diffrn_orient_matrix_UB_23      -0.005667
_diffrn_orient_matrix_UB_31      -0.120947
_diffrn_orient_matrix_UB_32      -0.011240
_diffrn_orient_matrix_UB_33      0.017886
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0850
_diffrn_reflns_av_unetI/netI     0.0873
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12559
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        65.052
_diffrn_reflns_theta_max         65.052
_diffrn_reflns_theta_min         6.625
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1604
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.1226
_refine_ls_R_factor_gt           0.0625
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0826P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1343
_refine_ls_wR_factor_ref         0.1764
_reflns_Friedel_coverage         0.000
_reflns_number_gt                820
_reflns_number_total             1604
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01428_si_002.cif
_cod_data_source_block           29
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4038692
_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
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C42(H42), C43(H43), C45(H45), C46(H46)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x-1/2, -y, 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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.0825(4) 0.57790(18) 0.27588(14) 0.0475(8) Uani 1 1 d . . . . .
N2 N 0.5050(4) 0.34157(19) 0.52890(15) 0.0516(9) Uani 1 1 d . . . . .
C2 C 0.0460(5) 0.6187(2) 0.31374(19) 0.0538(11) Uani 1 1 d . . . . .
H2 H 0.0614 0.6812 0.3050 0.065 Uiso 1 1 calc R . . . .
C3 C 0.1595(4) 0.5752(2) 0.36552(18) 0.0493(10) Uani 1 1 d . . . . .
H3 H 0.2429 0.6084 0.3930 0.059 Uiso 1 1 calc R . . . .
C4 C 0.1460(4) 0.4818(2) 0.37540(16) 0.0417(9) Uani 1 1 d . . . . .
C5 C -0.0083(4) 0.3376(2) 0.34152(16) 0.0409(9) Uani 1 1 d . . . . .
H5 H 0.0632 0.3042 0.3754 0.049 Uiso 1 1 calc R . . . .
C6 C -0.1302(4) 0.2939(2) 0.29810(16) 0.0400(9) Uani 1 1 d . . . . .
H6 H -0.1362 0.2302 0.2995 0.048 Uiso 1 1 calc R . . . .
C15 C -0.2500 0.4401(3) 0.2500 0.0349(12) Uani 1 2 d S T P . .
C16 C -0.2500 0.3439(3) 0.2500 0.0373(12) Uani 1 2 d S T P . .
C17 C -0.1082(4) 0.4864(2) 0.28874(16) 0.0397(9) Uani 1 1 d . . . . .
C18 C 0.0110(4) 0.4340(2) 0.33556(16) 0.0379(9) Uani 1 1 d . . . . .
C41 C 0.2706(4) 0.4318(2) 0.42761(17) 0.0411(9) Uani 1 1 d . . . . .
C42 C 0.2716(4) 0.4466(2) 0.51071(18) 0.0498(10) Uani 1 1 d . . . . .
H42 H 0.1937 0.4870 0.5340 0.060 Uiso 1 1 calc R . . . .
C43 C 0.3889(5) 0.4007(2) 0.55731(19) 0.0517(10) Uani 1 1 d . . . . .
H43 H 0.3874 0.4114 0.6123 0.062 Uiso 1 1 calc R . . . .
C45 C 0.5048(4) 0.3274(2) 0.44968(19) 0.0530(10) Uani 1 1 d . . . . .
H45 H 0.5843 0.2865 0.4283 0.064 Uiso 1 1 calc R . . . .
C46 C 0.3909(5) 0.3712(2) 0.39774(19) 0.0504(10) Uani 1 1 d . . . . .
H46 H 0.3960 0.3596 0.3429 0.060 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 0.0181 0.0091 '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 0.0311 0.0180 '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
_geom_angle_publ_flag
C2 N1 C17 118.4(3) . . ?
C43 N2 C45 116.7(3) . . ?
N1 C2 H2 117.6 . . ?
N1 C2 C3 124.8(3) . . ?
C3 C2 H2 117.6 . . ?
C2 C3 H3 120.7 . . ?
C4 C3 C2 118.6(3) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 C18 119.0(3) . . ?
C3 C4 C41 120.3(3) . . ?
C18 C4 C41 120.7(3) . . ?
C6 C5 H5 119.9 . . ?
C6 C5 C18 120.2(3) . . ?
C18 C5 H5 119.9 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C16 121.1(3) . . ?
C16 C6 H6 119.4 . . ?
C16 C15 C17 117.8(2) . 4_455 ?
C16 C15 C17 117.8(2) . . ?
C17 C15 C17 124.3(4) 4_455 . ?
C6 C16 C6 118.6(4) . 4_455 ?
C15 C16 C6 120.7(2) . 4_455 ?
C15 C16 C6 120.7(2) . . ?
N1 C17 C15 119.8(3) . . ?
N1 C17 C18 120.8(3) . . ?
C18 C17 C15 119.2(3) . . ?
C4 C18 C17 118.0(3) . . ?
C5 C18 C4 122.0(3) . . ?
C5 C18 C17 119.9(3) . . ?
C42 C41 C4 120.3(3) . . ?
C46 C41 C4 122.8(3) . . ?
C46 C41 C42 116.9(3) . . ?
C41 C42 H42 120.4 . . ?
C43 C42 C41 119.2(3) . . ?
C43 C42 H42 120.4 . . ?
N2 C43 C42 124.3(3) . . ?
N2 C43 H43 117.9 . . ?
C42 C43 H43 117.9 . . ?
N2 C45 H45 118.5 . . ?
N2 C45 C46 122.9(3) . . ?
C46 C45 H45 118.5 . . ?
C41 C46 C45 120.0(3) . . ?
C41 C46 H46 120.0 . . ?
C45 C46 H46 120.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.324(4) . ?
N1 C17 1.366(4) . ?
N2 C43 1.335(4) . ?
N2 C45 1.337(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(4) . ?
C4 C18 1.424(4) . ?
C4 C41 1.493(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.352(4) . ?
C5 C18 1.419(4) . ?
C6 H6 0.9300 . ?
C6 C16 1.430(3) . ?
C15 C16 1.403(5) . ?
C15 C17 1.445(4) . ?
C15 C17 1.445(4) 4_455 ?
C16 C6 1.430(3) 4_455 ?
C17 C18 1.432(4) . ?
C41 C42 1.403(4) . ?
C41 C46 1.379(4) . ?
C42 H42 0.9300 . ?
C42 C43 1.372(4) . ?
C43 H43 0.9300 . ?
C45 H45 0.9300 . ?
C45 C46 1.394(4) . ?
C46 H46 0.9300 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 4.1(6) . . . . ?
N1 C17 C18 C4 6.7(4) . . . . ?
N1 C17 C18 C5 -173.6(3) . . . . ?
N2 C45 C46 C41 -0.5(5) . . . . ?
C2 N1 C17 C15 178.4(3) . . . . ?
C2 N1 C17 C18 -6.2(4) . . . . ?
C2 C3 C4 C18 -3.2(5) . . . . ?
C2 C3 C4 C41 177.2(3) . . . . ?
C3 C4 C18 C5 178.5(3) . . . . ?
C3 C4 C18 C17 -1.9(4) . . . . ?
C3 C4 C41 C42 67.2(4) . . . . ?
C3 C4 C41 C46 -111.4(4) . . . . ?
C4 C41 C42 C43 -179.1(3) . . . . ?
C4 C41 C46 C45 179.3(3) . . . . ?
C5 C6 C16 C6 176.6(3) . . . 4_455 ?
C5 C6 C16 C15 -3.4(3) . . . . ?
C6 C5 C18 C4 -175.1(3) . . . . ?
C6 C5 C18 C17 5.3(4) . . . . ?
C15 C17 C18 C4 -177.8(2) . . . . ?
C15 C17 C18 C5 1.8(4) . . . . ?
C16 C15 C17 N1 166.1(2) . . . . ?
C16 C15 C17 C18 -9.5(3) . . . . ?
C17 N1 C2 C3 0.7(5) . . . . ?
C17 C15 C16 C6 -169.64(18) 4_455 . . . ?
C17 C15 C16 C6 10.37(18) 4_455 . . 4_455 ?
C17 C15 C16 C6 10.36(18) . . . . ?
C17 C15 C16 C6 -169.63(18) . . . 4_455 ?
C17 C15 C17 N1 -13.9(2) 4_455 . . . ?
C17 C15 C17 C18 170.5(3) 4_455 . . . ?
C18 C4 C41 C42 -112.4(3) . . . . ?
C18 C4 C41 C46 69.0(4) . . . . ?
C18 C5 C6 C16 -4.6(4) . . . . ?
C41 C4 C18 C5 -1.9(4) . . . . ?
C41 C4 C18 C17 177.7(3) . . . . ?
C41 C42 C43 N2 0.0(5) . . . . ?
C42 C41 C46 C45 0.6(5) . . . . ?
C43 N2 C45 C46 0.1(5) . . . . ?
C45 N2 C43 C42 0.1(5) . . . . ?
C46 C41 C42 C43 -0.4(5) . . . . ?
