Synthesis and Basicity Studies of Quinolino[7,8-h]quinoline Derivatives
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.; The Journal of Organic Chemistry  (2020) –; doi:10.1021/acs.joc.0c01428

data_4038691
_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 \w-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/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_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)
;
_shelx_res_checksum              47006
_shelx_hkl_checksum              50052
_olex2_submission_special_instructions 'No special instructions were received'