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_4038693
_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         'C16 H7 Cl N4 O5, C2 H3 N'
_chemical_formula_sum            'C18 H10 Cl N5 O5'
_chemical_formula_weight         411.76
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-12-04
_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                 95.267(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.8312(12)
_cell_length_b                   6.6242(9)
_cell_length_c                   12.7222(19)
_cell_measurement_reflns_used    495
_cell_measurement_temperature    123
_cell_measurement_theta_max      68.7
_cell_measurement_theta_min      7.0
_cell_volume                     825.02(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      123
_diffrn_detector                 RX
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
scan:
	Number of images: 60
	           Slice: 20.0000 - 200.0000
	     Image width: 3.0000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: -0.1435
scan:
	Number of images: 60
	           Slice: 20.0000 - 200.0000
	     Image width: 3.0000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 270.0000
	             XTD: 127.4000
	          2theta: -0.1259
scan:
	Number of images: 50
	           Slice: 20.0000 - 170.0000
	     Image width: 3.0000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 90.0000
	             XTD: 127.4000
	          2theta: -0.1259
scan:
	Number of images: 53
	           Slice: 24.0000 - 184.0000
	     Image width: 3.0000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 180.0000
	             XTD: 127.4000
	          2theta: -0.1259
scan:
	Number of images: 60
	           Slice: 20.0000 - 200.0000
	     Image width: 3.0000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: -0.1259
;
_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_orient_matrix_type       FS_PROCESS
_diffrn_orient_matrix_UB_11      -0.003145
_diffrn_orient_matrix_UB_12      0.008935
_diffrn_orient_matrix_UB_13      0.078205
_diffrn_orient_matrix_UB_21      0.100441
_diffrn_orient_matrix_UB_22      0.027328
_diffrn_orient_matrix_UB_23      0.008666
_diffrn_orient_matrix_UB_31      -0.018332
_diffrn_orient_matrix_UB_32      0.148197
_diffrn_orient_matrix_UB_33      -0.006313
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1035
_diffrn_reflns_av_unetI/netI     0.1196
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9287
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         72.038
_diffrn_reflns_theta_min         6.991
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.485
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         1729
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.1521
_refine_ls_R_factor_gt           0.0762
_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^)+(0.0949P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1589
_refine_ls_wR_factor_ref         0.2062
_reflns_Friedel_coverage         0.000
_reflns_number_gt                874
_reflns_number_total             1729
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01428_si_002.cif
_cod_data_source_block           33
_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               4038693
_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. Others
 Fixed Sof: O3(0.5) O4(0.5) N23(0.5) N26(0.5) H3AA(0.5) H3AB(0.5) H3AC(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C8(H8), C10(H10), C11(H11)
3.b Idealised Me refined as rotating group:
 C3AC(H3AA,H3AB,H3AC)
;
_shelx_res_checksum              76522
_shelx_hkl_checksum              85557
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'