#------------------------------------------------------------------------------
#$Date: 2019-11-28 21:10:36 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244630 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/92/7239278.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_7239278
loop_
_publ_author_name
'Dorazco-González, Alejandro'
'Alamo, Marcos Flores'
'Godoy-Alcántar, Carolina'
'Höpfl, Herbert'
'Yatsimirsky, Anatoly K.'
_publ_section_title
;
 Fluorescent anion sensing by bisquinolinium pyridine-2,6-dicarboxamide
 receptors in water
;
_journal_issue                   1
_journal_name_full               'RSC Adv.'
_journal_page_first              455
_journal_paper_doi               10.1039/C3RA44363A
_journal_volume                  4
_journal_year                    2014
_chemical_formula_moiety         'C17 H15 N2 O, C F3 O3 S'
_chemical_formula_sum            'C18 H15 F3 N2 O4 S'
_chemical_formula_weight         412.38
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.451(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3966(18)
_cell_length_b                   15.386(3)
_cell_length_c                   12.114(2)
_cell_measurement_reflns_used    4842
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.72
_cell_measurement_theta_min      2.53
_cell_volume                     1750.8(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16621
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3082
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.190
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0636
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0645P)²+1.1069P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1479
_refine_ls_wR_factor_ref         0.1526
_reflns_number_gt                2788
_reflns_number_total             3082
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra44363a.txt
_cod_data_source_block           jul4neum
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7239278
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.9093(3) 0.20809(17) 0.3118(2) 0.0433(6) Uani 1 1 d .
N2 N 0.4454(3) 0.26840(15) 0.4565(2) 0.0396(6) Uani 1 1 d D
H2' H 0.412(3) 0.2215(12) 0.427(3) 0.059 Uiso 1 1 d D
C1 C 0.8877(4) 0.1237(2) 0.3248(3) 0.0533(8) Uani 1 1 d .
H1 H 0.9569 0.0849 0.3020 0.064 Uiso 1 1 calc R
C2 C 0.7669(3) 0.0918(2) 0.3705(3) 0.0514(8) Uani 1 1 d .
H2 H 0.7548 0.0322 0.3789 0.062 Uiso 1 1 calc R
C3 C 0.6644(3) 0.14776(19) 0.4038(2) 0.0427(7) Uani 1 1 d .
H3 H 0.5834 0.1265 0.4372 0.051 Uiso 1 1 calc R
C4 C 0.6805(3) 0.23732(17) 0.3881(2) 0.0342(6) Uani 1 1 d .
C5 C 0.5759(3) 0.29980(18) 0.4176(2) 0.0358(6) Uani 1 1 d .
C6 C 0.6035(3) 0.38622(19) 0.4067(3) 0.0448(7) Uani 1 1 d .
H6 H 0.5365 0.4270 0.4280 0.054 Uiso 1 1 calc R
C7 C 0.7322(3) 0.4137(2) 0.3636(3) 0.0490(8) Uani 1 1 d .
H7 H 0.7496 0.4730 0.3576 0.059 Uiso 1 1 calc R
C8 C 0.8327(3) 0.3571(2) 0.3300(3) 0.0453(7) Uani 1 1 d .
H8 H 0.9163 0.3772 0.2994 0.054 Uiso 1 1 calc R
C9 C 0.8082(3) 0.26806(19) 0.3421(2) 0.0378(7) Uani 1 1 d .
C10 C 0.3598(3) 0.31124(18) 0.5281(2) 0.0372(6) Uani 1 1 d .
C11 C 0.2232(3) 0.26692(18) 0.5541(2) 0.0371(6) Uani 1 1 d .
C12 C 0.2050(3) 0.17818(19) 0.5522(3) 0.0477(8) Uani 1 1 d .
H12 H 0.2800 0.1423 0.5329 0.057 Uiso 1 1 calc R
C13 C 0.0757(4) 0.1423(2) 0.5789(3) 0.0549(9) Uani 1 1 d .
H13 H 0.0638 0.0823 0.5770 0.066 Uiso 1 1 calc R
C14 C -0.0352(4) 0.1945(2) 0.6081(3) 0.0522(8) Uani 1 1 d .
H14 H -0.1219 0.1700 0.6265 0.063 Uiso 1 1 calc R
C15 C -0.0183(4) 0.2824(2) 0.6101(3) 0.0577(9) Uani 1 1 d .
H15 H -0.0939 0.3179 0.6292 0.069 Uiso 1 1 calc R
C16 C 0.1110(3) 0.3191(2) 0.5840(3) 0.0494(8) Uani 1 1 d .
H16 H 0.1223 0.3791 0.5866 0.059 Uiso 1 1 calc R
C17 C 1.0460(3) 0.2373(2) 0.2671(3) 0.0604(9) Uani 1 1 d .
H17A H 1.1013 0.1876 0.2468 0.091 Uiso 1 1 calc R
H17B H 1.0974 0.2703 0.3222 0.091 Uiso 1 1 calc R
H17C H 1.0281 0.2729 0.2032 0.091 Uiso 1 1 calc R
S1 S 0.32142(9) 0.01671(5) 0.32986(6) 0.0448(3) Uani 1 1 d .
F1 F 0.2495(3) -0.09227(13) 0.17543(19) 0.0784(7) Uani 1 1 d .
F2 F 0.4004(3) 0.00198(15) 0.12599(18) 0.0801(7) Uani 1 1 d .
F3 F 0.1834(3) 0.03787(16) 0.1438(2) 0.0861(8) Uani 1 1 d .
C18 C 0.2870(4) -0.0093(2) 0.1859(3) 0.0515(8) Uani 1 1 d .
O1 O 0.3917(2) 0.38065(13) 0.56909(18) 0.0512(6) Uani 1 1 d .
O2 O 0.4348(3) -0.03998(19) 0.3601(2) 0.0809(8) Uani 1 1 d .
O3 O 0.1884(3) -0.00002(16) 0.3784(2) 0.0760(8) Uani 1 1 d .
O4 O 0.3565(3) 0.10737(15) 0.32602(19) 0.0622(7) Uani 1 1 d .
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
C1 N1 C9 121.0(3)
C1 N1 C17 118.6(3)
C9 N1 C17 120.4(3)
C10 N2 C5 125.3(2)
N1 C1 C2 122.1(3)
C3 C2 C1 119.6(3)
C2 C3 C4 120.2(3)
C3 C4 C9 118.5(3)
C3 C4 C5 123.5(3)
C9 C4 C5 118.0(2)
C6 C5 N2 122.4(3)
C6 C5 C4 120.0(3)
N2 C5 C4 117.6(2)
C5 C6 C7 120.1(3)
C8 C7 C6 122.4(3)
C7 C8 C9 118.7(3)
N1 C9 C8 120.7(3)
N1 C9 C4 118.5(3)
C8 C9 C4 120.8(3)
O1 C10 N2 122.8(3)
O1 C10 C11 121.4(3)
N2 C10 C11 115.8(2)
C12 C11 C16 119.0(3)
C12 C11 C10 123.8(3)
C16 C11 C10 117.1(3)
C11 C12 C13 120.2(3)
C14 C13 C12 120.4(3)
C15 C14 C13 119.9(3)
C14 C15 C16 120.3(3)
C11 C16 C15 120.2(3)
O2 S1 O3 116.46(18)
O2 S1 O4 115.77(17)
O3 S1 O4 113.32(15)
O2 S1 C18 103.14(16)
O3 S1 C18 102.78(17)
O4 S1 C18 102.69(15)
F3 C18 F2 108.5(3)
F3 C18 F1 107.7(3)
F2 C18 F1 106.9(3)
F3 C18 S1 111.4(2)
F2 C18 S1 112.0(2)
F1 C18 S1 110.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.324(4)
N1 C9 1.381(4)
N1 C17 1.476(4)
N2 C10 1.367(4)
N2 C5 1.411(4)
C1 C2 1.367(5)
C2 C3 1.361(4)
C3 C4 1.400(4)
C4 C9 1.417(4)
C4 C5 1.426(4)
C5 C6 1.362(4)
C6 C7 1.395(4)
C7 C8 1.354(4)
C8 C9 1.398(4)
C10 O1 1.212(3)
C10 C11 1.494(4)
C11 C12 1.376(4)
C11 C16 1.381(4)
C12 C13 1.380(4)
C13 C14 1.369(5)
C14 C15 1.362(5)
C15 C16 1.383(5)
S1 O2 1.418(3)
S1 O3 1.418(3)
S1 O4 1.434(2)
S1 C18 1.811(3)
F1 C18 1.329(4)
F2 C18 1.316(4)
F3 C18 1.308(4)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C9 N1 C1 C2 -1.5(5)
C17 N1 C1 C2 176.8(3)
N1 C1 C2 C3 0.3(5)
C1 C2 C3 C4 2.0(5)
C2 C3 C4 C9 -3.1(4)
C2 C3 C4 C5 178.0(3)
C10 N2 C5 C6 -29.1(4)
C10 N2 C5 C4 151.6(3)
C3 C4 C5 C6 175.5(3)
C9 C4 C5 C6 -3.4(4)
C3 C4 C5 N2 -5.1(4)
C9 C4 C5 N2 175.9(2)
N2 C5 C6 C7 -177.4(3)
C4 C5 C6 C7 1.9(4)
C5 C6 C7 C8 0.8(5)
C6 C7 C8 C9 -2.0(5)
C1 N1 C9 C8 178.9(3)
C17 N1 C9 C8 0.7(4)
C1 N1 C9 C4 0.3(4)
C17 N1 C9 C4 -177.9(3)
C7 C8 C9 N1 -178.2(3)
C7 C8 C9 C4 0.3(4)
C3 C4 C9 N1 1.9(4)
C5 C4 C9 N1 -179.1(2)
C3 C4 C9 C8 -176.7(3)
C5 C4 C9 C8 2.3(4)
C5 N2 C10 O1 -2.9(5)
C5 N2 C10 C11 177.5(2)
O1 C10 C11 C12 -151.0(3)
N2 C10 C11 C12 28.6(4)
O1 C10 C11 C16 27.4(4)
N2 C10 C11 C16 -153.0(3)
C16 C11 C12 C13 0.7(5)
C10 C11 C12 C13 179.1(3)
C11 C12 C13 C14 -0.4(5)
C12 C13 C14 C15 0.4(5)
C13 C14 C15 C16 -0.7(5)
C12 C11 C16 C15 -0.9(5)
C10 C11 C16 C15 -179.4(3)
C14 C15 C16 C11 0.9(5)
O2 S1 C18 F3 -180.0(3)
O3 S1 C18 F3 58.5(3)
O4 S1 C18 F3 -59.3(3)
O2 S1 C18 F2 -58.3(3)
O3 S1 C18 F2 -179.7(2)
O4 S1 C18 F2 62.4(3)
O2 S1 C18 F1 60.6(3)
O3 S1 C18 F1 -60.9(3)
O4 S1 C18 F1 -178.7(2)
