#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:46:17 +0200 (mar 06 de oct de 2020) $
#$Revision: 258123 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/10/7241055.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_7241055
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 Br2 O2)'
_chemical_formula_sum            'C17 H13 Br4 N O4'
_chemical_formula_weight         614.92
_chemical_name_common            Acridine+Dibromoacetate
_chemical_name_systematic        8
_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                103.479(2)
_cell_angle_beta                 96.829(3)
_cell_angle_gamma                95.388(3)
_cell_formula_units_Z            1
_cell_length_a                   6.3247(2)
_cell_length_b                   7.9047(4)
_cell_length_c                   10.1134(5)
_cell_measurement_reflns_used    1734
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      30.999
_cell_measurement_theta_min      0.407
_cell_volume                     484.31(4)
_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 0.994
_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  0.0362
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4378
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.248
_diffrn_reflns_theta_min         2.093
_exptl_absorpt_coefficient_mu    8.332
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.3936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.108
_exptl_crystal_description       plate
_exptl_crystal_F_000             294
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.902
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1936
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0407
_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)+(0.0123P)²+1.5291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0955
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1622
_reflns_number_total             1936
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra04691d2.cif
_cod_data_source_block           8
_cod_depositor_comments
'Adding full bibliography for 7241053--7241066.cif.'
_cod_database_code               7241055
_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   0.250
_shelx_estimated_absorpt_t_max   0.490
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 -0.0058(7) 0.4716(6) 0.1286(4) 0.0371(9) Uani 0.5 1 d . . P A 1
H10 H -0.009671 0.448697 0.225541 0.044 Uiso 0.5 1 calc R U P A 1
C9 C -0.0058(7) 0.4716(6) 0.1286(4) 0.0371(9) Uani 0.5 1 d . . P A 2
H9 H -0.009332 0.450678 0.217155 0.044 Uiso 0.5 1 calc R U P A 2
C1 C 0.3592(9) 0.7018(7) -0.0496(6) 0.0508(13) Uani 1 1 d . . . . .
H1 H 0.366265 0.724319 -0.137320 0.061 Uiso 1 1 calc R U . . .
C2 C 0.5231(9) 0.7678(8) 0.0547(7) 0.0569(15) Uani 1 1 d . . . . .
H2 H 0.644362 0.836845 0.038997 0.068 Uiso 1 1 calc R U . . .
C3 C 0.5177(9) 0.7365(8) 0.1852(6) 0.0570(15) Uani 1 1 d . . . . .
H3 H 0.635571 0.783240 0.255940 0.068 Uiso 1 1 calc R U . . .
C4 C 0.3457(8) 0.6401(7) 0.2115(5) 0.0449(12) Uani 1 1 d . . . . .
H4 H 0.343894 0.619313 0.300200 0.054 Uiso 1 1 calc R U . . .
C4A C 0.1687(7) 0.5703(6) 0.1066(4) 0.0348(10) Uani 1 1 d . . . . .
C9A C 0.1778(8) 0.5992(6) -0.0267(5) 0.0362(10) Uani 1 1 d . . . . .
Br1 Br 0.07881(9) 0.04949(7) 0.18430(5) 0.04916(18) Uani 1 1 d . . . . .
Br2 Br 0.50763(8) 0.19807(8) 0.39603(5) 0.0537(2) Uani 1 1 d . . . . .
O1 O 0.0597(8) 0.3824(5) 0.4124(4) 0.0702(13) Uani 1 1 d . . . . .
H1O H -0.000807 0.452528 0.466939 0.105 Uiso 0.5 1 calc R U P . .
O2 O 0.0507(6) 0.2312(5) 0.5701(4) 0.0531(9) Uani 1 1 d . . . . .
C11 C 0.0963(8) 0.2533(6) 0.4617(5) 0.0386(10) Uani 1 1 d . . . . .
C12 C 0.2061(7) 0.1123(6) 0.3751(5) 0.0355(10) Uani 1 1 d . . . . .
H12 H 0.191478 0.005371 0.411729 0.043 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'
Br Br -0.2901 2.4595 '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'
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 122.3(4) . 2_565 ?
C4A N10 H10 118.9 . . ?
C9A N10 H10 118.9 2_565 . ?
C4A C9 C9A 122.3(4) . 2_565 ?
C4A C9 H9 118.9 . . ?
C9A C9 H9 118.9 2_565 . ?
C2 C1 C9A 119.5(5) . . ?
C2 C1 H1 120.2 . . ?
C9A C1 H1 120.2 . . ?
C1 C2 C3 121.6(5) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 120.7(5) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C4A 120.0(5) . . ?
C3 C4 H4 120.0 . . ?
C4A C4 H4 120.0 . . ?
C9 C4A C4 121.7(4) . . ?
N10 C4A C4 121.7(4) . . ?
C9 C4A C9A 119.3(4) . . ?
N10 C4A C9A 119.3(4) . . ?
C4 C4A C9A 118.9(4) . . ?
N10 C9A C1 122.3(4) 2_565 . ?
N10 C9A C4A 118.4(4) 2_565 . ?
C1 C9A C4A 119.3(5) . . ?
C11 O1 H1O 109.5 . . ?
O2 C11 O1 126.1(5) . . ?
O2 C11 C12 117.6(4) . . ?
O1 C11 C12 116.4(4) . . ?
C11 C12 Br1 112.0(3) . . ?
C11 C12 Br2 108.1(3) . . ?
Br1 C12 Br2 111.3(2) . . ?
C11 C12 H12 108.5 . . ?
Br1 C12 H12 108.5 . . ?
Br2 C12 H12 108.5 . . ?
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 1.362(6) . ?
N10 C9A 1.382(6) 2_565 ?
N10 H10 1.0400 . ?
C9 C4A 1.362(6) . ?
C9 C9A 1.382(6) 2_565 ?
C9 H9 0.9500 . ?
C1 C2 1.357(8) . ?
C1 C9A 1.416(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.402(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.357(8) . ?
C3 H3 0.9500 . ?
C4 C4A 1.419(6) . ?
C4 H4 0.9500 . ?
C4A C9A 1.426(6) . ?
Br1 C12 1.931(4) . ?
Br2 C12 1.933(5) . ?
O1 C11 1.264(6) . ?
O1 H1O 0.8400 . ?
O2 C11 1.213(6) . ?
C11 C12 1.525(6) . ?
C12 H12 1.0000 . ?
