#------------------------------------------------------------------------------
#$Date: 2021-09-06 13:00:29 +0200 (lun 06 de sep de 2021) $
#$Revision: 268729 $
#$URL: svn://www.crystallography.net/cod/cif/7/70/76/7707678.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_7707678
loop_
_publ_author_name
'Vega, Manel'
'Blasco, Salvador'
'García-España, Enrique'
'Soberats, Bartolomé'
'Frontera, Antonio'
'Rotger, Carmen'
'Costa, Antonio'
_publ_section_title
;
 Dual role of silver in a fluorogenic N-squaraine probe based on
 Ag(I)-π interactions.
;
_journal_issue                   27
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              9367
_journal_page_last               9371
_journal_paper_doi               10.1039/d1dt01408k
_journal_volume                  50
_journal_year                    2021
_chemical_formula_moiety         'C18 H9 N4 O2, C16 H36 N'
_chemical_formula_sum            'C34 H45 N5 O2'
_chemical_formula_weight         555.75
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-04
_audit_creation_method
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-18 deposited with the CCDC.	2021-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                94.262(12)
_cell_angle_beta                 94.357(10)
_cell_angle_gamma                95.865(9)
_cell_formula_units_Z            2
_cell_length_a                   8.329(4)
_cell_length_b                   12.701(4)
_cell_length_c                   15.105(6)
_cell_measurement_reflns_used    9002
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      29.561
_cell_measurement_theta_min      2.468
_cell_volume                     1579.5(11)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0980
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            67593
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.590
_diffrn_reflns_theta_min         2.196
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1253 before and 0.0685 after correction.
The Ratio of minimum to maximum transmission is 0.9280.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.182
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     549
_refine_ls_number_reflns         8855
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0524
_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)+(0.0463P)²+0.5528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1323
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5550
_reflns_number_total             8855
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt01408k2.cif
_cod_data_source_block           mo_ma8_0m
_cod_depositor_comments          'Adding full bibliography for 7707678.cif.'
_cod_original_cell_volume        1579.6(11)
_cod_database_code               7707678
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
;
_olex2_submission_special_instructions 'No special instructions were received'
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
O1 O 0.50044(15) 0.36659(8) 0.44395(8) 0.0286(3) Uani 1 1 d . . . . .
N3 N 0.66337(16) 0.47149(10) 0.62524(9) 0.0209(3) Uani 1 1 d . . . . .
O2 O 0.78330(14) 0.22746(8) 0.66916(7) 0.0262(3) Uani 1 1 d . . . . .
N1 N 0.63355(16) 0.13014(9) 0.47513(9) 0.0220(3) Uani 1 1 d . . . . .
C1 C 0.58477(19) 0.32924(11) 0.50277(10) 0.0207(3) Uani 1 1 d . . . . .
N5 N 0.24760(16) 0.22336(10) 0.73624(9) 0.0239(3) Uani 1 1 d . . . . .
C11 C 0.65981(18) 0.36968(11) 0.58819(10) 0.0194(3) Uani 1 1 d . . . . .
C2 C 0.64235(19) 0.22333(11) 0.51599(10) 0.0200(3) Uani 1 1 d . . . . .
C10 C 0.71344(18) 0.26712(11) 0.60665(10) 0.0202(3) Uani 1 1 d . . . . .
C4 C 0.6261(2) 0.18725(13) 0.32342(11) 0.0263(4) Uani 1 1 d . . . . .
C23 C 0.1223(2) 0.15311(12) 0.78003(12) 0.0233(3) Uani 1 1 d . . . . .
C9 C 0.4596(2) 0.02960(12) 0.35512(11) 0.0237(3) Uani 1 1 d . . . . .
C12 C 0.72274(19) 0.51248(12) 0.70999(10) 0.0209(3) Uani 1 1 d . . . . .
C15 C 0.8381(2) 0.60206(12) 0.87990(11) 0.0244(3) Uani 1 1 d . . . . .
C14 C 0.8483(2) 0.49484(13) 0.85598(11) 0.0258(4) Uani 1 1 d . . . . .
C13 C 0.7911(2) 0.45012(12) 0.77214(11) 0.0242(3) Uani 1 1 d . . . . .
C31 C 0.1863(2) 0.33206(12) 0.73557(12) 0.0258(4) Uani 1 1 d . . . . .
C17 C 0.7691(2) 0.66456(13) 0.81771(11) 0.0271(4) Uani 1 1 d . . . . .
C16 C 0.8979(2) 0.64664(13) 0.96737(12) 0.0270(4) Uani 1 1 d . . . . .
C3 C 0.5716(2) 0.11766(12) 0.38513(11) 0.0231(3) Uani 1 1 d . . . . .
N4 N 0.9468(2) 0.68091(12) 1.03806(10) 0.0337(4) Uani 1 1 d . . . . .
C8 C 0.3981(2) 0.01495(13) 0.26716(11) 0.0259(4) Uani 1 1 d . . . . .
C24 C 0.1723(2) 0.04682(13) 0.80544(12) 0.0258(4) Uani 1 1 d . . . . .
C18 C 0.7124(2) 0.62061(12) 0.73395(12) 0.0261(4) Uani 1 1 d . . . . .
C5 C 0.5653(2) 0.17246(13) 0.23529(12) 0.0276(4) Uani 1 1 d . . . . .
C19 C 0.2676(2) 0.17688(14) 0.64234(12) 0.0280(4) Uani 1 1 d . . . . .
C25 C 0.0386(2) -0.00898(14) 0.85444(13) 0.0297(4) Uani 1 1 d . . . . .
C6 C 0.4504(2) 0.08680(13) 0.20613(11) 0.0266(4) Uani 1 1 d . . . . .
C27 C 0.4141(2) 0.23042(14) 0.78703(12) 0.0282(4) Uani 1 1 d . . . . .
N2 N 0.3365(2) 0.06959(14) 0.04099(11) 0.0445(4) Uani 1 1 d . . . . .
C20 C 0.1275(2) 0.17842(15) 0.57275(12) 0.0307(4) Uani 1 1 d . . . . .
C7 C 0.3871(2) 0.07450(14) 0.11412(12) 0.0310(4) Uani 1 1 d . . . . .
C21 C 0.1737(2) 0.13057(16) 0.48367(12) 0.0339(4) Uani 1 1 d . . . . .
C32 C 0.2995(2) 0.41603(14) 0.69864(15) 0.0345(4) Uani 1 1 d . . . . .
C28 C 0.4254(2) 0.27842(15) 0.88226(13) 0.0316(4) Uani 1 1 d . . . . .
C29 C 0.5883(2) 0.26296(16) 0.93051(14) 0.0354(4) Uani 1 1 d . . . . .
C26 C 0.0839(3) -0.11321(15) 0.88712(15) 0.0373(4) Uani 1 1 d . . . . .
C33 C 0.2196(3) 0.51917(15) 0.69151(15) 0.0402(5) Uani 1 1 d . . . . .
C22 C 0.0445(3) 0.1341(2) 0.40825(15) 0.0455(5) Uani 1 1 d . . . . .
C34 C 0.1018(3) 0.51524(19) 0.61165(18) 0.0503(6) Uani 1 1 d . . . . .
C30 C 0.6189(3) 0.3292(2) 1.01867(15) 0.0460(5) Uani 1 1 d . . . . .
H33A H 0.181(3) 0.5543(17) 0.7556(15) 0.055 Uiso 1 1 d R . . . .
H27A H 0.486(2) 0.2725(13) 0.7519(12) 0.023(4) Uiso 1 1 d . . . . .
H31A H 0.082(2) 0.3187(12) 0.7009(11) 0.019(4) Uiso 1 1 d . . . . .
H24A H 0.273(3) 0.0580(15) 0.8475(13) 0.040(5) Uiso 1 1 d . . . . .
H31B H 0.169(2) 0.3547(13) 0.7974(12) 0.022(4) Uiso 1 1 d . . . . .
H22A H 0.026(3) 0.2093(19) 0.3979(15) 0.053(7) Uiso 1 1 d . . . . .
H27B H 0.444(2) 0.1573(14) 0.7853(12) 0.028(5) Uiso 1 1 d . . . . .
H8 H 0.320(2) -0.0473(14) 0.2477(12) 0.029(5) Uiso 1 1 d . . . . .
H26A H 0.098(3) -0.1680(17) 0.8344(15) 0.048(6) Uiso 1 1 d . . . . .
H23A H 0.101(2) 0.1981(13) 0.8324(11) 0.021(4) Uiso 1 1 d . . . . .
H30A H 0.621(3) 0.4044(18) 1.0119(14) 0.044(6) Uiso 1 1 d . . . . .
H13 H 0.799(2) 0.3760(14) 0.7556(12) 0.028(5) Uiso 1 1 d . . . . .
H9 H 0.423(2) -0.0194(14) 0.3956(13) 0.031(5) Uiso 1 1 d . . . . .
H24B H 0.192(2) 0.0023(15) 0.7511(13) 0.034(5) Uiso 1 1 d . . . . .
H18 H 0.664(2) 0.6642(13) 0.6910(11) 0.024(4) Uiso 1 1 d . . . . .
H28A H 0.411(2) 0.3521(16) 0.8849(13) 0.037(5) Uiso 1 1 d . . . . .
H28B H 0.336(2) 0.2458(14) 0.9147(12) 0.030(5) Uiso 1 1 d . . . . .
H5 H 0.606(2) 0.2235(14) 0.1927(12) 0.031(5) Uiso 1 1 d . . . . .
H32A H 0.320(3) 0.3913(16) 0.6383(14) 0.042(6) Uiso 1 1 d . . . . .
H25A H -0.063(2) -0.0227(14) 0.8136(13) 0.037(5) Uiso 1 1 d . . . . .
H21A H 0.195(3) 0.0570(17) 0.4899(14) 0.045(6) Uiso 1 1 d . . . . .
H4 H 0.710(2) 0.2508(15) 0.3454(12) 0.032(5) Uiso 1 1 d . . . . .
H19A H 0.293(2) 0.1043(15) 0.6501(12) 0.033(5) Uiso 1 1 d . . . . .
H14 H 0.896(2) 0.4521(14) 0.9007(12) 0.032(5) Uiso 1 1 d . . . . .
H17 H 0.763(2) 0.7397(15) 0.8339(12) 0.036(5) Uiso 1 1 d . . . . .
H20A H 0.102(2) 0.2505(16) 0.5670(13) 0.041(6) Uiso 1 1 d . . . . .
H25B H 0.016(2) 0.0386(15) 0.9064(13) 0.037(5) Uiso 1 1 d . . . . .
H20B H 0.026(2) 0.1363(14) 0.5889(12) 0.033(5) Uiso 1 1 d . . . . .
H26B H 0.191(3) -0.0980(17) 0.9250(15) 0.051(6) Uiso 1 1 d . . . . .
H23B H 0.026(2) 0.1433(13) 0.7373(12) 0.027(5) Uiso 1 1 d . . . . .
H19B H 0.367(2) 0.2171(14) 0.6253(12) 0.031(5) Uiso 1 1 d . . . . .
H29A H 0.589(3) 0.1861(17) 0.9423(14) 0.047(6) Uiso 1 1 d . . . . .
H29B H 0.677(3) 0.2807(15) 0.8919(13) 0.040(5) Uiso 1 1 d . . . . .
H21B H 0.278(3) 0.1713(16) 0.4694(13) 0.042(6) Uiso 1 1 d . . . . .
H32B H 0.411(3) 0.4324(17) 0.7413(15) 0.055(6) Uiso 1 1 d . . . . .
H33B H 0.313(3) 0.5813(17) 0.6896(14) 0.053(6) Uiso 1 1 d . . . . .
H26C H 0.000(3) -0.1432(17) 0.9223(15) 0.052(6) Uiso 1 1 d . . . . .
H30B H 0.722(3) 0.3153(18) 1.0506(16) 0.061(7) Uiso 1 1 d . . . . .
H22B H -0.066(3) 0.0964(19) 0.4210(16) 0.068(8) Uiso 1 1 d . . . . .
H34A H 0.169(3) 0.508(2) 0.5538(18) 0.079(8) Uiso 1 1 d . . . . .
H34B H 0.002(3) 0.4538(19) 0.6121(15) 0.062(7) Uiso 1 1 d . . . . .
H22C H 0.078(3) 0.1020(19) 0.3495(18) 0.069(8) Uiso 1 1 d . . . . .
H30C H 0.529(3) 0.3160(18) 1.0568(16) 0.062(7) Uiso 1 1 d . . . . .
H34C H 0.048(3) 0.588(2) 0.6073(17) 0.081(8) Uiso 1 1 d . . . . .
H3 H 0.613(2) 0.5142(13) 0.5908(12) 0.024(4) Uiso 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'
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
C11 N3 C12 128.27(13) . . ?
C2 N1 C3 117.71(13) . . ?
O1 C1 C11 134.23(14) . . ?
O1 C1 C2 135.49(14) . . ?
C11 C1 C2 90.21(12) . . ?
C31 N5 C23 106.26(12) . . ?
C31 N5 C19 111.52(13) . . ?
C31 N5 C27 111.00(13) . . ?
C19 N5 C23 110.64(13) . . ?
C19 N5 C27 106.15(13) . . ?
C27 N5 C23 111.34(13) . . ?
N3 C11 C1 126.02(13) . . ?
N3 C11 C10 141.59(14) . . ?
C1 C11 C10 92.39(12) . . ?
N1 C2 C1 139.43(15) . . ?
N1 C2 C10 132.17(14) . . ?
C10 C2 C1 88.29(12) . . ?
O2 C10 C11 137.80(15) . . ?
O2 C10 C2 133.15(14) . . ?
C11 C10 C2 89.02(12) . . ?
C5 C4 C3 120.61(16) . . ?
C24 C23 N5 116.12(14) . . ?
C8 C9 C3 120.49(15) . . ?
N3 C12 C13 122.22(14) . . ?
N3 C12 C18 118.29(14) . . ?
C13 C12 C18 119.49(15) . . ?
C14 C15 C17 119.43(15) . . ?
C14 C15 C16 119.65(14) . . ?
C17 C15 C16 120.92(15) . . ?
C13 C14 C15 120.65(15) . . ?
C14 C13 C12 119.96(15) . . ?
C32 C31 N5 114.50(14) . . ?
C18 C17 C15 120.23(15) . . ?
N4 C16 C15 178.87(17) . . ?
C4 C3 N1 121.66(15) . . ?
C4 C3 C9 118.92(15) . . ?
C9 C3 N1 119.30(14) . . ?
C9 C8 C6 120.12(16) . . ?
C23 C24 C25 109.07(14) . . ?
C17 C18 C12 120.24(15) . . ?
C4 C5 C6 120.36(16) . . ?
C20 C19 N5 117.35(14) . . ?
C26 C25 C24 112.28(16) . . ?
C8 C6 C7 121.47(16) . . ?
C5 C6 C8 119.42(16) . . ?
C5 C6 C7 119.11(16) . . ?
C28 C27 N5 115.73(14) . . ?
C19 C20 C21 108.86(15) . . ?
N2 C7 C6 176.90(19) . . ?
C22 C21 C20 112.91(17) . . ?
C31 C32 C33 110.55(16) . . ?
C27 C28 C29 110.47(16) . . ?
C30 C29 C28 111.91(18) . . ?
C34 C33 C32 112.99(19) . . ?
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
O1 C1 1.2424(18) . ?
N3 C11 1.3668(19) . ?
N3 C12 1.381(2) . ?
O2 C10 1.2373(18) . ?
N1 C2 1.2861(19) . ?
N1 C3 1.409(2) . ?
C1 C11 1.426(2) . ?
C1 C2 1.496(2) . ?
N5 C23 1.525(2) . ?
N5 C31 1.521(2) . ?
N5 C19 1.523(2) . ?
N5 C27 1.524(2) . ?
C11 C10 1.459(2) . ?
C2 C10 1.494(2) . ?
C4 C3 1.400(2) . ?
C4 C5 1.380(2) . ?
C23 C24 1.520(2) . ?
C9 C3 1.405(2) . ?
C9 C8 1.379(2) . ?
C12 C13 1.398(2) . ?
C12 C18 1.407(2) . ?
C15 C14 1.396(2) . ?
C15 C17 1.401(2) . ?
C15 C16 1.430(2) . ?
C14 C13 1.378(2) . ?
C31 C32 1.517(2) . ?
C17 C18 1.373(2) . ?
C16 N4 1.151(2) . ?
C8 C6 1.406(2) . ?
C24 C25 1.527(2) . ?
C5 C6 1.395(2) . ?
C19 C20 1.512(3) . ?
C25 C26 1.520(3) . ?
C6 C7 1.440(3) . ?
C27 C28 1.512(3) . ?
N2 C7 1.147(2) . ?
C20 C21 1.527(3) . ?
C21 C22 1.513(3) . ?
C32 C33 1.536(3) . ?
C28 C29 1.528(3) . ?
C29 C30 1.511(3) . ?
C33 C34 1.490(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3 O1 0.891(18) 1.950(18) 2.8035(17) 159.9(16) 2_666 yes
