#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:46:17 +0200 (mar 06 de oct de 2020) $
#$Revision: 258123 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/10/7241056.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_7241056
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, 2(C2 H1.50 Cl2 O2)'
_chemical_formula_sum            'C17 H13 Cl4 N O4'
_chemical_formula_weight         437.08
_chemical_name_common            Acridine+Dichloroacetate
_chemical_name_systematic        7
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_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                104.058(3)
_cell_angle_beta                 96.799(2)
_cell_angle_gamma                95.159(3)
_cell_formula_units_Z            1
_cell_length_a                   6.0822(3)
_cell_length_b                   7.8975(4)
_cell_length_c                   9.9912(19)
_cell_measurement_reflns_used    1530
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      30.999
_cell_measurement_theta_min      0.407
_cell_volume                     458.75(9)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0229
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3384
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.096
_diffrn_reflns_theta_max         25.096
_diffrn_reflns_theta_min         2.124
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_description       plate
_exptl_crystal_F_000             222
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1624
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0457
_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)+(0.0026P)²+0.8000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1209
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1433
_reflns_number_total             1624
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra04691d2.cif
_cod_data_source_block           7
_cod_depositor_comments
'Adding full bibliography for 7241053--7241066.cif.'
_cod_database_code               7241056
_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   0.845
_shelx_estimated_absorpt_t_max   0.924
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
N10 N 0.0005(5) 0.4695(4) 0.1303(3) 0.0323(6) Uani 0.5 1 d . . P A 1
H10N H 0.001409 0.445572 0.228196 0.039 Uiso 0.5 1 calc R U P A 1
C9 C 0.0005(5) 0.4695(4) 0.1303(3) 0.0323(6) Uani 0.5 1 d . . P A 2
H9 H 0.001326 0.447645 0.219724 0.039 Uiso 0.5 1 calc R U P A 2
C1 C 0.3608(6) 0.7115(4) -0.0519(4) 0.0434(9) Uani 1 1 d . . . . .
H1 H 0.363576 0.734555 -0.140748 0.052 Uiso 1 1 calc R U . . .
C2 C 0.5331(6) 0.7804(4) 0.0536(5) 0.0496(10) Uani 1 1 d . . . . .
H2 H 0.656875 0.850892 0.037014 0.059 Uiso 1 1 calc R U . . .
C3 C 0.5315(6) 0.7494(5) 0.1857(4) 0.0485(10) Uani 1 1 d . . . . .
H3 H 0.653570 0.800240 0.257079 0.058 Uiso 1 1 calc R U . . .
C4 C 0.3601(6) 0.6488(4) 0.2139(4) 0.0406(8) Uani 1 1 d . . . . .
H4 H 0.362087 0.627847 0.303726 0.049 Uiso 1 1 calc R U . . .
C4A C 0.1761(5) 0.5744(4) 0.1067(3) 0.0324(7) Uani 1 1 d . . . . .
C9A C 0.1780(5) 0.6052(4) -0.0272(3) 0.0319(7) Uani 1 1 d . . . . .
Cl1 Cl 0.09575(14) 0.05894(11) 0.19153(9) 0.0430(3) Uani 1 1 d . . . . .
Cl2 Cl 0.49944(14) 0.18557(13) 0.39324(10) 0.0506(3) Uani 1 1 d . . . . .
O1 O 0.0635(6) 0.3832(3) 0.4108(3) 0.0805(12) Uani 1 1 d . . . . .
H1O H 0.000337 0.454602 0.465797 0.121 Uiso 0.5 1 calc R U P . .
O2 O 0.0431(4) 0.2294(3) 0.5671(3) 0.0436(6) Uani 1 1 d . . . . .
C11 C 0.0958(5) 0.2520(4) 0.4598(4) 0.0339(7) Uani 1 1 d . . . . .
C12 C 0.2107(5) 0.1099(4) 0.3697(3) 0.0327(7) Uani 1 1 d . . . . .
H12 H 0.191527 0.000761 0.403282 0.039 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
C4A N10 C9A 121.7(3) . 2_565 ?
C4A N10 H10N 119.2 . . ?
C9A N10 H10N 119.2 2_565 . ?
C4A C9 C9A 121.7(3) . 2_565 ?
C4A C9 H9 119.2 . . ?
C9A C9 H9 119.2 2_565 . ?
C2 C1 C9A 119.1(4) . . ?
C2 C1 H1 120.5 . . ?
C9A C1 H1 120.5 . . ?
C1 C2 C3 121.4(3) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C4A 119.0(4) . . ?
C3 C4 H4 120.5 . . ?
C4A C4 H4 120.5 . . ?
C9 C4A C9A 119.5(3) . . ?
N10 C4A C9A 119.5(3) . . ?
C9 C4A C4 120.9(3) . . ?
N10 C4A C4 120.9(3) . . ?
C9A C4A C4 119.6(3) . . ?
N10 C9A C1 121.7(3) 2_565 . ?
N10 C9A C4A 118.8(3) 2_565 . ?
C1 C9A C4A 119.5(3) . . ?
C11 O1 H1O 109.5 . . ?
O2 C11 O1 126.3(3) . . ?
O2 C11 C12 118.4(3) . . ?
O1 C11 C12 115.3(3) . . ?
C11 C12 Cl1 112.0(2) . . ?
C11 C12 Cl2 108.1(2) . . ?
Cl1 C12 Cl2 110.83(18) . . ?
C11 C12 H12 108.6 . . ?
Cl1 C12 H12 108.6 . . ?
Cl2 C12 H12 108.6 . . ?
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
N10 C4A 1.370(4) . ?
N10 C9A 1.383(4) 2_565 ?
N10 H10N 1.0400 . ?
C9 C4A 1.370(4) . ?
C9 C9A 1.383(4) 2_565 ?
C9 H9 0.9500 . ?
C1 C2 1.365(5) . ?
C1 C9A 1.414(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.401(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.352(5) . ?
C3 H3 0.9500 . ?
C4 C4A 1.427(5) . ?
C4 H4 0.9500 . ?
C4A C9A 1.418(5) . ?
Cl1 C12 1.768(3) . ?
Cl2 C12 1.772(3) . ?
O1 C11 1.270(4) . ?
O1 H1O 0.8400 . ?
O2 C11 1.203(4) . ?
C11 C12 1.535(4) . ?
C12 H12 1.0000 . ?
