#------------------------------------------------------------------------------
#$Date: 2023-12-22 17:07:40 +0200 (Fri, 22 Dec 2023) $
#$Revision: 288505 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/94/7059462.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_7059462
loop_
_publ_author_name
'Esteves, Catarina V.'
'Costa, Judite'
'Bernard, Hélène'
'Tripier, Raphaël'
'Delgado, Rita'
_publ_section_title
;
 A squaraine-based dipicolylamine derivative acting as a turn-on
 mercury(ii) fluorescent probe in water
;
_journal_issue                   16
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6589
_journal_page_last               6600
_journal_paper_doi               10.1039/D0NJ00852D
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C28 H24 N6 O2'
_chemical_formula_sum            'C28 H24 N6 O2'
_chemical_formula_weight         476.53
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-07-17T18:36:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-03-27 deposited with the CCDC.	2020-04-01 downloaded from the CCDC.
;
_cell_angle_alpha                74.229(3)
_cell_angle_beta                 84.864(3)
_cell_angle_gamma                75.053(3)
_cell_formula_units_Z            2
_cell_length_a                   8.6784(3)
_cell_length_b                   9.8570(4)
_cell_length_c                   14.6836(5)
_cell_measurement_reflns_used    4175
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.758
_cell_measurement_theta_min      3.666
_cell_volume                     1167.64(8)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics
;
        ORTEP3 for Windows (Farrugia, 1997)
        MERCURY  (Bruno et al., 2002)
;
_computing_publication_material
;
        WinGX (Farrugia, 1999)
        PLATON (Spek, 1990-2003)
        enCIFer (Allen et al., 2004)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      170(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.3622
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0361085
_diffrn_orient_matrix_UB_12      0.0580865
_diffrn_orient_matrix_UB_13      -0.0217141
_diffrn_orient_matrix_UB_21      0.076521
_diffrn_orient_matrix_UB_22      -0.0481686
_diffrn_orient_matrix_UB_23      0.0091354
_diffrn_orient_matrix_UB_31      0.000084
_diffrn_orient_matrix_UB_32      -0.0158086
_diffrn_orient_matrix_UB_33      -0.0443364
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13691
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.47
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
        model based on expressions derived by R.C. Clark & J.S. Reid.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'hexagonal tilted plate // (1 0 1)'
_exptl_crystal_F_000             500
_exptl_crystal_recrystallization_method
'from solution in methanol at room temperature,by slow evaporation of solvent'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4765
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.068
_refine_ls_R_factor_gt           0.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0404P)²+0.2402P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.1009
_reflns_number_gt                3494
_reflns_number_total             4765
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            d0nj00852d2.cif
_cod_data_source_block           cvert3-b
_cod_depositor_comments
;Adding full bibliography for 7059462.cif.

 Adding full bibliography for 7059462.cif.

The following automatic conversions were performed:

data name '_iucr_refine_instruction_details' was replaced with
'_iucr_refine_instructions_details' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_cell_volume        1167.64(7)
_cod_original_sg_symbol_Hall     -P1
_cod_database_code               7059462
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.41261(16) 0.08211(16) 0.01571(10) 0.0241(3) Uani 1 1 d . . .
C2 C 0.51756(17) -0.04891(16) 0.07230(10) 0.0252(3) Uani 1 1 d . . .
C3 C 0.20847(17) 0.30568(16) -0.03748(11) 0.0268(3) Uani 1 1 d . . .
H1A H 0.095 0.3272 -0.0169 0.032 Uiso 1 1 calc R . .
H1B H 0.2156 0.2723 -0.0959 0.032 Uiso 1 1 calc R . .
C4 C 0.26713(16) 0.44255(16) -0.05894(10) 0.0249(3) Uani 1 1 d . . .
C5 C 0.37812(18) 0.46873(17) -0.13094(11) 0.0311(4) Uani 1 1 d . . .
H5 H 0.4186 0.4006 -0.1675 0.037 Uiso 1 1 calc R . .
C6 C 0.42942(19) 0.59518(18) -0.14909(12) 0.0361(4) Uani 1 1 d . . .
H6 H 0.5058 0.6153 -0.1982 0.043 Uiso 1 1 calc R . .
C7 C 0.36830(19) 0.69122(18) -0.09506(11) 0.0338(4) Uani 1 1 d . . .
H7 H 0.4014 0.779 -0.1058 0.041 Uiso 1 1 calc R . .
C8 C 0.2579(2) 0.65720(18) -0.02500(12) 0.0350(4) Uani 1 1 d . . .
H8 H 0.2157 0.7244 0.012 0.042 Uiso 1 1 calc R . .
C9 C 0.25094(18) 0.18061(17) 0.13503(10) 0.0285(4) Uani 1 1 d . . .
H9A H 0.2223 0.2798 0.1446 0.034 Uiso 1 1 calc R . .
H9B H 0.3412 0.1222 0.1767 0.034 Uiso 1 1 calc R . .
C10 C 0.10938(17) 0.11338(16) 0.16354(10) 0.0258(3) Uani 1 1 d . . .
C11 C 0.02944(18) 0.11994(18) 0.24882(11) 0.0318(4) Uani 1 1 d . . .
H11 H 0.0562 0.1739 0.2871 0.038 Uiso 1 1 calc R . .
C12 C -0.08962(19) 0.04690(19) 0.27737(12) 0.0388(4) Uani 1 1 d . . .
H12 H -0.1437 0.0472 0.3365 0.047 Uiso 1 1 calc R . .
C13 C -0.12882(19) -0.02660(19) 0.21861(12) 0.0388(4) Uani 1 1 d . . .
H13 H -0.2105 -0.0776 0.2362 0.047 Uiso 1 1 calc R . .
C14 C -0.0464(2) -0.02402(18) 0.13396(12) 0.0376(4) Uani 1 1 d . . .
H14 H -0.0757 -0.0724 0.0929 0.045 Uiso 1 1 calc R . .
N1 N 0.30149(14) 0.18867(13) 0.03694(8) 0.0258(3) Uani 1 1 d . . .
N2 N 0.20590(15) 0.53545(14) -0.00549(9) 0.0323(3) Uani 1 1 d . . .
N3 N 0.07288(16) 0.04281(15) 0.10581(9) 0.0331(3) Uani 1 1 d . . .
O1 O 0.53871(13) -0.10597(12) 0.15776(7) 0.0355(3) Uani 1 1 d . . .
C15 C 0.41893(16) 0.59101(16) 0.46704(10) 0.0237(3) Uani 1 1 d . . .
C16 C 0.53289(17) 0.47552(16) 0.43503(10) 0.0241(3) Uani 1 1 d . . .
C17 C 0.22646(18) 0.81407(16) 0.47444(11) 0.0295(4) Uani 1 1 d . . .
H17A H 0.2418 0.7708 0.5432 0.035 Uiso 1 1 calc R . .
H17B H 0.1113 0.8347 0.4622 0.035 Uiso 1 1 calc R . .
C18 C 0.27804(17) 0.95536(16) 0.44637(10) 0.0262(3) Uani 1 1 d . . .
C19 C 0.40831(18) 0.97704(18) 0.38723(11) 0.0316(4) Uani 1 1 d . . .
H19 H 0.4735 0.9006 0.3631 0.038 Uiso 1 1 calc R . .
C20 C 0.44093(19) 1.11274(19) 0.36427(12) 0.0371(4) Uani 1 1 d . . .
H20 H 0.5297 1.1308 0.3243 0.045 Uiso 1 1 calc R . .
C21 C 0.3434(2) 1.22105(19) 0.39992(12) 0.0383(4) Uani 1 1 d . . .
H21 H 0.3616 1.3158 0.3837 0.046 Uiso 1 1 calc R . .
C22 C 0.2189(2) 1.18900(18) 0.45964(12) 0.0359(4) Uani 1 1 d . . .
H22 H 0.1535 1.2635 0.4855 0.043 Uiso 1 1 calc R . .
C23 C 0.27648(18) 0.72930(18) 0.32474(11) 0.0313(4) Uani 1 1 d . . .
H23A H 0.3761 0.6981 0.2895 0.038 Uiso 1 1 calc R . .
H23B H 0.2317 0.834 0.296 0.038 Uiso 1 1 calc R . .
C24 C 0.15888(17) 0.64531(16) 0.31405(11) 0.0283(4) Uani 1 1 d . . .
C25 C 0.16072(18) 0.59983(18) 0.23273(11) 0.0337(4) Uani 1 1 d . . .
H25 H 0.2399 0.6158 0.1847 0.04 Uiso 1 1 calc R . .
C26 C 0.0464(2) 0.53097(18) 0.22194(12) 0.0370(4) Uani 1 1 d . . .
H26 H 0.0449 0.5003 0.1661 0.044 Uiso 1 1 calc R . .
C27 C -0.0653(2) 0.50744(19) 0.29328(12) 0.0380(4) Uani 1 1 d . . .
H27 H -0.1462 0.4612 0.2878 0.046 Uiso 1 1 calc R . .
C28 C -0.0561(2) 0.5531(2) 0.37309(12) 0.0411(4) Uani 1 1 d . . .
H28 H -0.1318 0.535 0.4229 0.049 Uiso 1 1 calc R . .
N4 N 0.31459(14) 0.70918(13) 0.42341(9) 0.0275(3) Uani 1 1 d . . .
N5 N 0.18462(15) 1.05894(14) 0.48341(9) 0.0308(3) Uani 1 1 d . . .
N6 N 0.05303(16) 0.62157(15) 0.38476(9) 0.0356(3) Uani 1 1 d . . .
O2 O 0.57249(12) 0.44712(11) 0.35806(7) 0.0314(3) 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.025
0 1 3 0.135
0 1 1 0.12
0 -1 -1 0.105
0 0 1 0.13
1 0 1 0.08
-1 0 -1 0.05
-1 -1 -1 0.075
1 1 1 0.085
0 -1 1 0.12
0 1 -1 0.1
-1 0 0 0.025
-1 -1 1 0.105
0 0 -1 0.11
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
N1 C1 C2 134.78(14) . 2_655 ?
N1 C1 C2 133.64(14) . . ?
C2 C1 C2 91.57(12) 2_655 . ?
N1 C1 C1 178.98(15) . 2_655 ?
C2 C1 C1 45.79(8) 2_655 2_655 ?
C2 C1 C1 45.78(8) . 2_655 ?
O1 C2 C1 135.92(14) . 2_655 ?
O1 C2 C1 135.65(14) . . ?
C1 C2 C1 88.43(12) 2_655 . ?
N1 C3 C4 112.04(12) . . ?
N1 C3 H1A 109.2 . . ?
C4 C3 H1A 109.2 . . ?
N1 C3 H1B 109.2 . . ?
C4 C3 H1B 109.2 . . ?
H1A C3 H1B 107.9 . . ?
N2 C4 C5 122.75(14) . . ?
N2 C4 C3 116.82(13) . . ?
C5 C4 C3 120.43(14) . . ?
C6 C5 C4 119.15(15) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C7 C6 C5 118.89(15) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C6 C7 C8 118.31(15) . . ?
C6 C7 H7 120.8 . . ?
C8 C7 H7 120.8 . . ?
N2 C8 C7 124.27(16) . . ?
N2 C8 H8 117.9 . . ?
C7 C8 H8 117.9 . . ?
N1 C9 C10 112.70(12) . . ?
N1 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
N3 C10 C11 122.78(14) . . ?
N3 C10 C9 117.15(13) . . ?
C11 C10 C9 119.98(14) . . ?
C12 C11 C10 119.02(15) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 118.93(15) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C14 C13 C12 118.20(15) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
N3 C14 C13 123.98(16) . . ?
N3 C14 H14 118 . . ?
C13 C14 H14 118 . . ?
C1 N1 C9 120.00(12) . . ?
C1 N1 C3 121.11(13) . . ?
C9 N1 C3 118.17(12) . . ?
C8 N2 C4 116.64(13) . . ?
C10 N3 C14 117.04(14) . . ?
N4 C15 C16 133.64(14) . . ?
N4 C15 C16 134.81(14) . 2_666 ?
C16 C15 C16 91.55(12) . 2_666 ?
N4 C15 C15 179.39(16) . 2_666 ?
C16 C15 C15 45.80(8) . 2_666 ?
C16 C15 C15 45.74(8) 2_666 2_666 ?
O2 C16 C15 135.72(14) . . ?
O2 C16 C15 135.83(15) . 2_666 ?
C15 C16 C15 88.45(12) . 2_666 ?
N4 C17 C18 112.94(12) . . ?
N4 C17 H17A 109 . . ?
C18 C17 H17A 109 . . ?
N4 C17 H17B 109 . . ?
C18 C17 H17B 109 . . ?
H17A C17 H17B 107.8 . . ?
N5 C18 C19 122.90(14) . . ?
N5 C18 C17 113.43(13) . . ?
C19 C18 C17 123.67(14) . . ?
C20 C19 C18 118.37(16) . . ?
C20 C19 H19 120.8 . . ?
C18 C19 H19 120.8 . . ?
C21 C20 C19 119.25(15) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C20 C21 C22 118.43(15) . . ?
C20 C21 H21 120.8 . . ?
C22 C21 H21 120.8 . . ?
N5 C22 C21 123.72(16) . . ?
N5 C22 H22 118.1 . . ?
C21 C22 H22 118.1 . . ?
N4 C23 C24 113.25(12) . . ?
N4 C23 H23A 108.9 . . ?
C24 C23 H23A 108.9 . . ?
N4 C23 H23B 108.9 . . ?
C24 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
N6 C24 C25 122.61(15) . . ?
N6 C24 C23 117.10(14) . . ?
C25 C24 C23 120.27(14) . . ?
C26 C25 C24 119.35(15) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C27 C26 C25 118.98(16) . . ?
C27 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
C26 C27 C28 117.89(16) . . ?
C26 C27 H27 121.1 . . ?
C28 C27 H27 121.1 . . ?
N6 C28 C27 124.17(16) . . ?
N6 C28 H28 117.9 . . ?
C27 C28 H28 117.9 . . ?
C15 N4 C17 120.82(13) . . ?
C15 N4 C23 119.67(13) . . ?
C17 N4 C23 119.30(12) . . ?
C22 N5 C18 117.29(14) . . ?
C24 N6 C28 116.97(14) . . ?
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
C1 N1 1.3160(19) . ?
C1 C2 1.460(2) 2_655 ?
C1 C2 1.461(2) . ?
C2 O1 1.2366(17) . ?
C2 C1 1.460(2) 2_655 ?
C3 N1 1.4726(18) . ?
C3 C4 1.508(2) . ?
C3 H1A 0.99 . ?
C3 H1B 0.99 . ?
C4 N2 1.3423(19) . ?
C4 C5 1.382(2) . ?
C5 C6 1.381(2) . ?
C5 H5 0.95 . ?
C6 C7 1.371(2) . ?
C6 H6 0.95 . ?
C7 C8 1.375(2) . ?
C7 H7 0.95 . ?
C8 N2 1.340(2) . ?
C8 H8 0.95 . ?
C9 N1 1.4546(19) . ?
C9 C10 1.517(2) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 N3 1.3361(19) . ?
C10 C11 1.385(2) . ?
C11 C12 1.380(2) . ?
C11 H11 0.95 . ?
C12 C13 1.380(2) . ?
C12 H12 0.95 . ?
C13 C14 1.375(2) . ?
C13 H13 0.95 . ?
C14 N3 1.343(2) . ?
C14 H14 0.95 . ?
C15 N4 1.3196(18) . ?
C15 C16 1.457(2) . ?
C15 C16 1.458(2) 2_666 ?
C16 O2 1.2356(17) . ?
C16 C15 1.458(2) 2_666 ?
C17 N4 1.4581(19) . ?
C17 C18 1.512(2) . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C18 N5 1.338(2) . ?
C18 C19 1.388(2) . ?
C19 C20 1.384(2) . ?
C19 H19 0.95 . ?
C20 C21 1.374(2) . ?
C20 H20 0.95 . ?
C21 C22 1.376(2) . ?
C21 H21 0.95 . ?
C22 N5 1.337(2) . ?
C22 H22 0.95 . ?
C23 N4 1.4640(19) . ?
C23 C24 1.512(2) . ?
C23 H23A 0.99 . ?
C23 H23B 0.99 . ?
C24 N6 1.3360(19) . ?
C24 C25 1.382(2) . ?
C25 C26 1.380(2) . ?
C25 H25 0.95 . ?
C26 C27 1.376(2) . ?
C26 H26 0.95 . ?
C27 C28 1.380(2) . ?
C27 H27 0.95 . ?
C28 N6 1.342(2) . ?
C28 H28 0.95 . ?
