#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:46:17 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258123 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/10/7241062.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_7241062
loop_
_publ_author_name
'Tervola, Essi'
'Truong, Khai-Nghi'
'Ward, Jas S.'
'Priimagi, Arri'
'Rissanen, Kari'
_publ_section_title
;
 Fluorescence enhancement of quinolines by protonation
;
_journal_issue                   49
_journal_name_full               'RSC Advances'
_journal_page_first              29385
_journal_page_last               29393
_journal_paper_doi               10.1039/D0RA04691D
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C13 H10 N, C2 H Cl2 O2, C2 H2 Cl2 O2'
_chemical_formula_sum            'C17 H13 Cl4 N O4'
_chemical_formula_weight         437.08
_chemical_name_common            Benzoquinoline+Dichloroacetate
_chemical_name_systematic        13
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2020-05-04 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.939(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4155(3)
_cell_length_b                   11.3195(5)
_cell_length_c                   19.7432(8)
_cell_measurement_reflns_used    4984
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      30.508
_cell_measurement_theta_min      0.407
_cell_volume                     1878.25(13)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10664
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.246
_diffrn_reflns_theta_min         2.423
_exptl_absorpt_coefficient_mu    0.653
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6414
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3787
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0501
_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)+(0.0396P)²+1.4530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1239
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2567
_reflns_number_total             3787
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra04691d2.cif
_cod_data_source_block           13
_cod_depositor_comments
'Adding full bibliography for 7241053--7241066.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7241062
_shelx_shelxl_version_number     2017/1
_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_min   0.849
_shelx_estimated_absorpt_t_max   0.870
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6162(3) 0.53984(18) 0.39351(12) 0.0441(6) Uani 1 1 d . . . . .
H1N H 0.650285 0.627154 0.386633 0.053 Uiso 1 1 calc R U . . .
C1A C 0.6702(3) 0.4830(2) 0.45101(14) 0.0392(6) Uani 1 1 d . . . . .
C2 C 0.5221(4) 0.4893(3) 0.34579(16) 0.0545(8) Uani 1 1 d . . . . .
H2 H 0.488337 0.533445 0.306744 0.065 Uiso 1 1 calc R U . . .
C3 C 0.4730(4) 0.3743(3) 0.35198(18) 0.0576(8) Uani 1 1 d . . . . .
H3 H 0.405752 0.338545 0.317714 0.069 Uiso 1 1 calc R U . . .
C4 C 0.5230(4) 0.3128(2) 0.40848(18) 0.0553(9) Uani 1 1 d . . . . .
H4 H 0.490170 0.233064 0.413453 0.066 Uiso 1 1 calc R U . . .
C4A C 0.6220(3) 0.3650(2) 0.45942(16) 0.0466(7) Uani 1 1 d . . . . .
C5 C 0.6727(4) 0.3045(3) 0.51976(19) 0.0632(9) Uani 1 1 d . . . . .
H5 H 0.639670 0.225310 0.526543 0.076 Uiso 1 1 calc R U . . .
C6 C 0.7667(5) 0.3580(3) 0.56716(19) 0.0686(10) Uani 1 1 d . . . . .
H6 H 0.799401 0.315410 0.606914 0.082 Uiso 1 1 calc R U . . .
C6A C 0.8196(4) 0.4776(3) 0.55992(16) 0.0542(8) Uani 1 1 d . . . . .
C7 C 0.9154(5) 0.5345(3) 0.6103(2) 0.0735(11) Uani 1 1 d . . . . .
H7 H 0.948651 0.492094 0.650026 0.088 Uiso 1 1 calc R U . . .
C8 C 0.9618(5) 0.6482(4) 0.6037(2) 0.0774(11) Uani 1 1 d . . . . .
H8 H 1.026447 0.684558 0.638570 0.093 Uiso 1 1 calc R U . . .
C9 C 0.9147(4) 0.7119(3) 0.5457(2) 0.0687(10) Uani 1 1 d . . . . .
H9 H 0.947823 0.791593 0.541055 0.082 Uiso 1 1 calc R U . . .
C10 C 0.8209(4) 0.6598(2) 0.49557(17) 0.0530(8) Uani 1 1 d . . . . .
H10 H 0.789084 0.703921 0.456243 0.064 Uiso 1 1 calc R U . . .
C10A C 0.7711(3) 0.5421(2) 0.50146(15) 0.0428(7) Uani 1 1 d . . . . .
Cl1 Cl 0.73431(10) 1.08620(6) 0.31222(5) 0.0619(3) Uani 1 1 d . . . . .
Cl2 Cl 0.68275(16) 0.98858(9) 0.44473(5) 0.0947(4) Uani 1 1 d . . . . .
O1 O 0.6152(3) 0.76781(17) 0.36154(12) 0.0667(7) Uani 1 1 d . . . . .
O2 O 0.7997(3) 0.83800(16) 0.29577(13) 0.0623(6) Uani 1 1 d . . . . .
C11 C 0.6920(3) 0.8474(2) 0.33585(15) 0.0418(7) Uani 1 1 d . . . . .
C12 C 0.6410(4) 0.9723(2) 0.35665(15) 0.0451(7) Uani 1 1 d . . . . .
H12 H 0.523366 0.979409 0.347571 0.054 Uiso 1 1 calc R U . . .
Cl3 Cl 0.76538(10) 0.35408(6) 0.22820(5) 0.0627(3) Uani 1 1 d . . . . .
Cl4 Cl 0.85562(15) 0.46026(8) 0.10269(5) 0.0867(4) Uani 1 1 d . . . . .
O3 O 0.8909(3) 0.63839(18) 0.25916(12) 0.0606(6) Uani 1 1 d . . . . .
H3O H 0.847(5) 0.717(4) 0.273(2) 0.111(14) Uiso 1 1 d . . . . .
O4 O 0.6724(3) 0.6219(2) 0.19382(15) 0.0870(9) Uani 1 1 d . . . . .
C13 C 0.7998(3) 0.5874(2) 0.21442(15) 0.0426(7) Uani 1 1 d . . . . .
C14 C 0.8705(3) 0.4709(2) 0.19135(15) 0.0434(7) Uani 1 1 d . . . . .
H14 H 0.985065 0.466861 0.207326 0.052 Uiso 1 1 calc R U . . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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 C1A 123.3(2) . . ?
C2 N1 H1N 118.4 . . ?
C1A N1 H1N 118.4 . . ?
N1 C1A C4A 117.4(3) . . ?
N1 C1A C10A 121.1(2) . . ?
C4A C1A C10A 121.5(3) . . ?
N1 C2 C3 121.1(3) . . ?
N1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 118.4(3) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C4A 121.2(3) . . ?
C3 C4 H4 119.4 . . ?
C4A C4 H4 119.4 . . ?
C4 C4A C1A 118.6(3) . . ?
C4 C4A C5 122.7(3) . . ?
C1A C4A C5 118.7(3) . . ?
C6 C5 C4A 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C4A C5 H5 119.7 . . ?
C5 C6 C6A 122.2(3) . . ?
C5 C6 H6 118.9 . . ?
C6A C6 H6 118.9 . . ?
C7 C6A C10A 118.3(3) . . ?
C7 C6A C6 122.2(3) . . ?
C10A C6A C6 119.5(3) . . ?
C8 C7 C6A 121.8(4) . . ?
C8 C7 H7 119.1 . . ?
C6A C7 H7 119.1 . . ?
C7 C8 C9 120.1(3) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C10A 120.9(3) . . ?
C9 C10 H10 119.6 . . ?
C10A C10 H10 119.6 . . ?
C10 C10A C6A 119.0(3) . . ?
C10 C10A C1A 123.5(3) . . ?
C6A C10A C1A 117.5(3) . . ?
O1 C11 O2 128.0(3) . . ?
O1 C11 C12 113.7(3) . . ?
O2 C11 C12 118.2(2) . . ?
C11 C12 Cl2 108.33(19) . . ?
C11 C12 Cl1 113.6(2) . . ?
Cl2 C12 Cl1 109.97(15) . . ?
C11 C12 H12 108.3 . . ?
Cl2 C12 H12 108.3 . . ?
Cl1 C12 H12 108.3 . . ?
C13 O3 H3O 112(2) . . ?
O4 C13 O3 125.8(3) . . ?
O4 C13 C14 122.6(3) . . ?
O3 C13 C14 111.5(2) . . ?
C13 C14 Cl4 110.4(2) . . ?
C13 C14 Cl3 108.2(2) . . ?
Cl4 C14 Cl3 110.34(14) . . ?
C13 C14 H14 109.3 . . ?
Cl4 C14 H14 109.3 . . ?
Cl3 C14 H14 109.3 . . ?
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
N1 C2 1.329(4) . ?
N1 C1A 1.362(3) . ?
N1 H1N 1.0400 . ?
C1A C4A 1.409(4) . ?
C1A C10A 1.439(4) . ?
C2 C3 1.373(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.364(5) . ?
C3 H3 0.9500 . ?
C4 C4A 1.403(4) . ?
C4 H4 0.9500 . ?
C4A C5 1.421(4) . ?
C5 C6 1.339(5) . ?
C5 H5 0.9500 . ?
C6 C6A 1.434(5) . ?
C6 H6 0.9500 . ?
C6A C7 1.404(5) . ?
C6A C10A 1.408(4) . ?
C7 C8 1.352(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.392(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.368(4) . ?
C9 H9 0.9500 . ?
C10 C10A 1.404(4) . ?
C10 H10 0.9500 . ?
Cl1 C12 1.766(3) . ?
Cl2 C12 1.766(3) . ?
O1 C11 1.233(3) . ?
O2 C11 1.238(3) . ?
C11 C12 1.539(4) . ?
C12 H12 1.0000 . ?
Cl3 C14 1.768(3) . ?
Cl4 C14 1.753(3) . ?
O3 C13 1.277(3) . ?
O3 H3O 1.00(4) . ?
O4 C13 1.192(3) . ?
C13 C14 1.526(4) . ?
C14 H14 1.0000 . ?
