#------------------------------------------------------------------------------
#$Date: 2020-08-14 02:05:52 +0300 (Fri, 14 Aug 2020) $
#$Revision: 255298 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/86/4038691.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_4038691
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         'C21 H13 N3 O, H2 O'
_chemical_formula_sum            'C21 H15 N3 O2'
_chemical_formula_weight         341.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-06-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.510(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.83530(10)
_cell_length_b                   23.3888(6)
_cell_length_c                   16.9879(12)
_cell_measurement_reflns_used    4574
_cell_measurement_temperature    123
_cell_measurement_theta_max      71.7
_cell_measurement_theta_min      7.6
_cell_volume                     1521.01(12)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      123
_diffrn_detector                 RX
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
;
scan:
	Number of images: 64
	           Slice: 20.0000 - 180.0000
	     Image width: 2.5000
	        Exp time: 72.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 270.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 71
	           Slice: 20.0000 - 197.5000
	     Image width: 2.5000
	        Exp time: 72.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 270.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 56
	           Slice: 49.0000 - 189.0000
	     Image width: 2.5000
	        Exp time: 72.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 72
	           Slice: 20.0000 - 200.0000
	     Image width: 2.5000
	        Exp time: 72.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 90.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 68
	           Slice: 21.0000 - 191.0000
	     Image width: 2.5000
	        Exp time: 72.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 180.0000
	             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_radiation_monochromator  Confocal
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8314
_diffrn_reflns_point_group_measured_fraction_full 0.867
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.065
_diffrn_reflns_theta_min         7.576
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.795
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.647
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   Multi-scan
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Chip
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 975 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.843
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         2512
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.843
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0333
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0952
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_full    0.746
_reflns_Friedel_fraction_max     0.700
_reflns_number_gt                2419
_reflns_number_total             2512
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01428_si_002.cif
_cod_data_source_block           28
_cod_database_code               4038691
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.925
_shelx_estimated_absorpt_t_min   0.598
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C8(H8), C15(H15), C21(H21), C20(H20), C7(H7), C16(H16),
 C5(H5), C4(H4), C2(H2A), C3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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'
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
C9 C 0.2693(6) 0.18059(9) 0.08552(12) 0.0165(5) Uani 1 1 d . . . . .
C17 C 0.2460(6) -0.01739(10) -0.02042(11) 0.0169(5) Uani 1 1 d . . . . .
C14 C 0.2610(6) 0.08255(9) 0.02846(11) 0.0158(5) Uani 1 1 d . . . . .
C13 C 0.1225(6) 0.06236(10) 0.09853(11) 0.0166(5) Uani 1 1 d . . . . .
C10 C 0.3321(6) 0.14302(9) 0.02185(12) 0.0154(4) Uani 1 1 d . . . . .
N2 N 0.4561(5) 0.05698(8) -0.10162(10) 0.0181(4) Uani 1 1 d . . . . .
N1 N 0.4585(5) 0.16284(8) -0.04651(10) 0.0179(4) Uani 1 1 d . . . . .
C6 C 0.3462(6) 0.23963(9) 0.07624(12) 0.0159(4) Uani 1 1 d . . . . .
O1 O 0.2673(5) -0.11271(7) -0.06897(9) 0.0238(4) Uani 1 1 d . . . . .
C12 C 0.0534(6) 0.10143(10) 0.16018(11) 0.0183(5) Uani 1 1 d . . . . .
H12 H -0.041726 0.087632 0.205518 0.022 Uiso 1 1 calc R U . . .
C11 C 0.1222(6) 0.15786(9) 0.15460(11) 0.0171(5) Uani 1 1 d . . . . .
H11 H 0.073865 0.182184 0.195848 0.021 Uiso 1 1 calc R U . . .
C1 C 0.3059(6) 0.28266(9) 0.14037(12) 0.0166(4) Uani 1 1 d . . . . .
C18 C 0.3221(6) 0.04073(9) -0.03200(12) 0.0157(5) Uani 1 1 d . . . . .
C8 C 0.5158(6) 0.21844(9) -0.05369(12) 0.0194(5) Uani 1 1 d . . . . .
H8 H 0.595822 0.231713 -0.100939 0.023 Uiso 1 1 calc R U . . .
C15 C 0.0442(6) 0.00313(10) 0.10793(12) 0.0190(5) Uani 1 1 d . . . . .
H15 H -0.048718 -0.009378 0.154204 0.023 Uiso 1 1 calc R U . . .
C19 C 0.3192(6) -0.06029(9) -0.08041(13) 0.0190(5) Uani 1 1 d . . . . .
C21 C 0.5184(6) 0.01864(9) -0.15868(12) 0.0205(5) Uani 1 1 d . . . . .
H21 H 0.608445 0.031683 -0.205008 0.025 Uiso 1 1 calc R U . . .
C20 C 0.4548(7) -0.03815(9) -0.15102(13) 0.0216(5) Uani 1 1 d . . . . .
H20 H 0.499625 -0.062923 -0.192012 0.026 Uiso 1 1 calc R U . . .
C7 C 0.4626(6) 0.25829(9) 0.00590(12) 0.0188(5) Uani 1 1 d . . . . .
H7 H 0.505576 0.296923 -0.002088 0.023 Uiso 1 1 calc R U . . .
C16 C 0.1037(6) -0.03516(9) 0.05012(12) 0.0188(5) Uani 1 1 d . . . . .
H16 H 0.049971 -0.073525 0.057171 0.023 Uiso 1 1 calc R U . . .
C5 C 0.1416(6) 0.33480(9) 0.12268(13) 0.0181(5) Uani 1 1 d . . . . .
H5 H 0.047234 0.342350 0.072015 0.022 Uiso 1 1 calc R U . . .
C4 C 0.1221(6) 0.37502(10) 0.18205(13) 0.0208(5) Uani 1 1 d . . . . .
H4 H 0.005314 0.409032 0.169899 0.025 Uiso 1 1 calc R U . . .
N3 N 0.2608(6) 0.36820(8) 0.25612(11) 0.0217(4) Uani 1 1 d . . . . .
C2 C 0.4472(6) 0.27447(9) 0.21697(11) 0.0187(5) Uani 1 1 d . . . . .
H2A H 0.556612 0.240240 0.231439 0.022 Uiso 1 1 calc R U . . .
C3 C 0.4220(7) 0.31840(9) 0.27143(12) 0.0201(5) Uani 1 1 d . . . . .
H3 H 0.524085 0.312764 0.321909 0.024 Uiso 1 1 calc R U . . .
O2 O 0.7602(6) 0.17150(7) 0.33427(11) 0.0306(4) Uani 1 1 d . . . . .
H2 H 0.514(9) 0.0958(13) -0.1035(16) 0.029(8) Uiso 1 1 d . . . . .
H2B H 0.575(12) 0.1609(15) 0.363(2) 0.051(10) Uiso 1 1 d . . . . .
H2C H 0.949(11) 0.1513(15) 0.360(2) 0.050(10) Uiso 1 1 d . . . . .
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'
O O 0.0492 0.0322 '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
C10 C9 C11 119.03(18) . . ?
C6 C9 C10 117.94(18) . . ?
C6 C9 C11 123.00(19) . . ?
C18 C17 C19 120.85(19) . . ?
C18 C17 C16 119.90(19) . . ?
C16 C17 C19 119.25(19) . . ?
C13 C14 C10 118.32(18) . . ?
C13 C14 C18 117.19(18) . . ?
C10 C14 C18 124.49(18) . . ?
C14 C13 C12 120.01(19) . . ?
C14 C13 C15 120.69(19) . . ?
C12 C13 C15 119.29(18) . . ?
C9 C10 C14 120.18(17) . . ?
N1 C10 C9 121.39(18) . . ?
N1 C10 C14 118.43(17) . . ?
C18 N2 H2 113.6(17) . . ?
C21 N2 C18 121.76(18) . . ?
C21 N2 H2 124.5(18) . . ?
C8 N1 C10 118.71(18) . . ?
C9 C6 C1 122.69(18) . . ?
C7 C6 C9 119.07(19) . . ?
C7 C6 C1 118.24(19) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 C13 121.91(18) . . ?
C11 C12 H12 119.0 . . ?
C9 C11 H11 119.7 . . ?
C12 C11 C9 120.51(19) . . ?
C12 C11 H11 119.7 . . ?
C5 C1 C6 119.69(19) . . ?
C2 C1 C6 122.39(19) . . ?
C2 C1 C5 117.77(19) . . ?
C17 C18 C14 120.64(19) . . ?
N2 C18 C17 118.70(19) . . ?
N2 C18 C14 120.66(19) . . ?
N1 C8 H8 118.2 . . ?
N1 C8 C7 123.64(19) . . ?
C7 C8 H8 118.2 . . ?
C13 C15 H15 119.6 . . ?
C16 C15 C13 120.84(19) . . ?
C16 C15 H15 119.6 . . ?
O1 C19 C17 121.3(2) . . ?
O1 C19 C20 123.4(2) . . ?
C20 C19 C17 115.36(18) . . ?
N2 C21 H21 118.7 . . ?
N2 C21 C20 122.6(2) . . ?
C20 C21 H21 118.7 . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.67(19) . . ?
C21 C20 H20 119.7 . . ?
C6 C7 C8 119.18(19) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C17 C16 H16 119.6 . . ?
C15 C16 C17 120.73(19) . . ?
C15 C16 H16 119.6 . . ?
C1 C5 H5 120.6 . . ?
C4 C5 C1 118.7(2) . . ?
C4 C5 H5 120.6 . . ?
C5 C4 H4 117.8 . . ?
N3 C4 C5 124.4(2) . . ?
N3 C4 H4 117.8 . . ?
C3 N3 C4 115.90(18) . . ?
C1 C2 H2A 120.6 . . ?
C3 C2 C1 118.8(2) . . ?
C3 C2 H2A 120.6 . . ?
N3 C3 C2 124.4(2) . . ?
N3 C3 H3 117.8 . . ?
C2 C3 H3 117.8 . . ?
H2B O2 H2C 102(3) . . ?
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
C9 C10 1.425(3) . ?
C9 C6 1.423(3) . ?
C9 C11 1.435(3) . ?
C17 C18 1.407(3) . ?
C17 C19 1.469(3) . ?
C17 C16 1.409(3) . ?
C14 C13 1.414(3) . ?
C14 C10 1.446(3) . ?
C14 C18 1.448(3) . ?
C13 C12 1.427(3) . ?
C13 C15 1.428(3) . ?
C10 N1 1.367(3) . ?
N2 C18 1.372(3) . ?
N2 C21 1.352(3) . ?
N2 H2 0.94(3) . ?
N1 C8 1.326(3) . ?
C6 C1 1.498(3) . ?
C6 C7 1.372(3) . ?
O1 C19 1.259(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.350(3) . ?
C11 H11 0.9300 . ?
C1 C5 1.397(3) . ?
C1 C2 1.392(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.400(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.359(3) . ?
C19 C20 1.433(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.358(3) . ?
C20 H20 0.9300 . ?
C7 H7 0.9300 . ?
C16 H16 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.384(3) . ?
C4 H4 0.9300 . ?
C4 N3 1.345(3) . ?
N3 C3 1.337(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.390(3) . ?
C3 H3 0.9300 . ?
O2 H2B 0.92(5) . ?
O2 H2C 0.95(4) . ?
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
C9 C10 N1 C8 -1.5(3) . . . . ?
C9 C6 C1 C5 -134.2(2) . . . . ?
C9 C6 C1 C2 50.2(3) . . . . ?
C9 C6 C7 C8 -2.5(3) . . . . ?
C17 C19 C20 C21 2.0(3) . . . . ?
C14 C13 C12 C11 -1.2(3) . . . . ?
C14 C13 C15 C16 0.6(3) . . . . ?
C14 C10 N1 C8 178.3(2) . . . . ?
C13 C14 C10 C9 1.2(3) . . . . ?
C13 C14 C10 N1 -178.5(2) . . . . ?
C13 C14 C18 C17 -0.1(3) . . . . ?
C13 C14 C18 N2 -179.97(19) . . . . ?
C13 C12 C11 C9 -0.1(4) . . . . ?
C13 C15 C16 C17 0.3(3) . . . . ?
C10 C9 C6 C1 -177.2(2) . . . . ?
C10 C9 C6 C7 2.7(3) . . . . ?
C10 C9 C11 C12 1.9(3) . . . . ?
C10 C14 C13 C12 0.6(3) . . . . ?
C10 C14 C13 C15 179.4(2) . . . . ?
C10 C14 C18 C17 179.8(2) . . . . ?
C10 C14 C18 N2 0.0(3) . . . . ?
C10 N1 C8 C7 1.7(4) . . . . ?
N2 C21 C20 C19 -0.6(4) . . . . ?
N1 C8 C7 C6 0.3(4) . . . . ?
C6 C9 C10 C14 179.52(19) . . . . ?
C6 C9 C10 N1 -0.7(3) . . . . ?
C6 C9 C11 C12 179.8(2) . . . . ?
C6 C1 C5 C4 -176.9(2) . . . . ?
C6 C1 C2 C3 175.0(2) . . . . ?
O1 C19 C20 C21 -177.3(2) . . . . ?
C12 C13 C15 C16 179.4(2) . . . . ?
C11 C9 C10 C14 -2.5(3) . . . . ?
C11 C9 C10 N1 177.3(2) . . . . ?
C11 C9 C6 C1 4.8(3) . . . . ?
C11 C9 C6 C7 -175.3(2) . . . . ?
C1 C6 C7 C8 177.41(19) . . . . ?
C1 C5 C4 N3 2.1(3) . . . . ?
C1 C2 C3 N3 2.0(4) . . . . ?
C18 C17 C19 O1 176.6(2) . . . . ?
C18 C17 C19 C20 -2.8(3) . . . . ?
C18 C17 C16 C15 -1.1(3) . . . . ?
C18 C14 C13 C12 -179.5(2) . . . . ?
C18 C14 C13 C15 -0.6(3) . . . . ?
C18 C14 C10 C9 -178.72(19) . . . . ?
C18 C14 C10 N1 1.5(3) . . . . ?
C18 N2 C21 C20 -0.3(4) . . . . ?
C15 C13 C12 C11 180.0(2) . . . . ?
C19 C17 C18 C14 -177.79(18) . . . . ?
C19 C17 C18 N2 2.0(3) . . . . ?
C19 C17 C16 C15 177.7(2) . . . . ?
C21 N2 C18 C17 -0.5(3) . . . . ?
C21 N2 C18 C14 179.4(2) . . . . ?
C7 C6 C1 C5 45.9(3) . . . . ?
C7 C6 C1 C2 -129.7(2) . . . . ?
C16 C17 C18 C14 1.0(3) . . . . ?
C16 C17 C18 N2 -179.16(19) . . . . ?
C16 C17 C19 O1 -2.2(3) . . . . ?
C16 C17 C19 C20 178.4(2) . . . . ?
C5 C1 C2 C3 -0.7(3) . . . . ?
C5 C4 N3 C3 -0.9(3) . . . . ?
C4 N3 C3 C2 -1.1(3) . . . . ?
C2 C1 C5 C4 -1.1(3) . . . . ?
