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#$Date: 2020-02-04 22:30:09 +0200 (Tue, 04 Feb 2020) $
#$Revision: 247702 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/22/7702265.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_7702265
loop_
_publ_author_name
'Moro, Artur J.'
'Avó, João'
'Malfois, Marc'
'Zaccaria, Francesco'
'Fonseca Guerra, Célia'
'Caparrós, Francisco J'
'Rodríguez, Laura'
'Lima, João Carlos'
_publ_section_title
;
 Aggregation induced emission of a new naphthyridine-ethynyl-gold(i)
 complex as a potential tool for sensing guanosine nucleotides in aqueous
 media.
;
_journal_issue                   1
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              171
_journal_page_last               178
_journal_paper_doi               10.1039/c9dt04162a
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C12 H9 N3 O'
_chemical_formula_sum            'C12 H9 N3 O'
_chemical_formula_weight         211.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-05-13 deposited with the CCDC.	2019-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.7530(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.8320(8)
_cell_length_b                   7.2057(3)
_cell_length_c                   12.0342(4)
_cell_measurement_reflns_used    7811
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      25.69
_cell_measurement_theta_min      2.96
_cell_volume                     2038.99(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP and Mercury'
_computing_publication_material  'WingX and enCIFer'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16950
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.700
_diffrn_reflns_theta_min         3.466
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.7068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         1931
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0351
_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)+(0.0538P)²+1.4289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.0986
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1693
_reflns_number_total             1931
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9dt04162a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7702265.cif.'
_cod_original_sg_symbol_Hall     '-C 2yn'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7702265
_shelx_shelxl_version_number     2016/6
_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   0.982
_shelx_estimated_absorpt_t_max   0.991
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N2 N 0.96024(4) 0.22108(15) 0.10509(9) 0.0138(2) Uani 1 1 d . .
O1 O 1.11003(4) 0.43235(14) 0.06589(8) 0.0233(3) Uani 1 1 d . .
C8 C 0.86044(5) 0.04454(19) -0.17249(11) 0.0187(3) Uani 1 1 d . .
H8 H 0.857581 0.020564 -0.250112 0.022 Uiso 1 1 calc R U
N3 N 0.86933(4) 0.10983(15) 0.06321(9) 0.0147(3) Uani 1 1 d . .
C11 C 0.77433(5) 0.01135(18) 0.02694(11) 0.0181(3) Uani 1 1 d . .
C7 C 0.91329(5) 0.14950(17) 0.02335(10) 0.0134(3) Uani 1 1 d . .
N1 N 1.05102(4) 0.32711(15) 0.16404(9) 0.0158(3) Uani 1 1 d . .
C6 C 0.91081(5) 0.11951(17) -0.09430(11) 0.0154(3) Uani 1 1 d . .
C4 C 1.00580(5) 0.24077(18) -0.04453(11) 0.0174(3) Uani 1 1 d . .
H4 H 1.037588 0.274657 -0.064702 0.021 Uiso 1 1 calc R U
C5 C 0.95912(5) 0.16840(18) -0.12544(11) 0.0176(3) Uani 1 1 d . .
H5 H 0.958929 0.150802 -0.202126 0.021 Uiso 1 1 calc R U
C3 C 1.00469(5) 0.26341(17) 0.07252(11) 0.0141(3) Uani 1 1 d . .
C10 C 0.82208(5) 0.04398(18) -0.01408(11) 0.0161(3) Uani 1 1 d . .
C1 C 1.10010(5) 0.40795(18) 0.15802(11) 0.0178(3) Uani 1 1 d . .
C9 C 0.81606(5) 0.00770(19) -0.13295(11) 0.0193(3) Uani 1 1 d . .
H9 H 0.782275 -0.040581 -0.183279 0.023 Uiso 1 1 calc R U
C2 C 1.14113(6) 0.4644(2) 0.27428(12) 0.0232(3) Uani 1 1 d . .
H2A H 1.167368 0.364929 0.305327 0.035 Uiso 1 1 calc R U
H2B H 1.120623 0.491909 0.327673 0.035 Uiso 1 1 calc R U
H2C H 1.161676 0.572599 0.264347 0.035 Uiso 1 1 calc R U
C12 C 0.73283(5) -0.0130(2) 0.05342(12) 0.0234(3) Uani 1 1 d . .
H12 H 0.700277 -0.032171 0.074194 0.028 Uiso 1 1 calc R U
H1 H 1.0471(6) 0.309(2) 0.2343(14) 0.018(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
C3 N2 C7 118.44(10)
C9 C8 C6 119.12(11)
C9 C8 H8 120.4
C6 C8 H8 120.4
C10 N3 C7 117.23(10)
C12 C11 C10 175.71(13)
N3 C7 N2 115.06(10)
N3 C7 C6 122.74(11)
N2 C7 C6 122.19(11)
C1 N1 C3 128.36(11)
C1 N1 H1 118.7(9)
C3 N1 H1 112.9(9)
C8 C6 C5 124.49(11)
C8 C6 C7 118.10(11)
C5 C6 C7 117.41(11)
C5 C4 C3 118.01(11)
C5 C4 H4 121.0
C3 C4 H4 121.0
C4 C5 C6 120.57(11)
C4 C5 H5 119.7
C6 C5 H5 119.7
N2 C3 N1 113.52(10)
N2 C3 C4 123.35(11)
N1 C3 C4 123.10(11)
N3 C10 C9 123.83(11)
N3 C10 C11 117.17(11)
C9 C10 C11 118.99(11)
O1 C1 N1 123.34(12)
O1 C1 C2 122.18(11)
N1 C1 C2 114.49(11)
C8 C9 C10 118.94(12)
C8 C9 H9 120.5
C10 C9 H9 120.5
C1 C2 H2A 109.5
C1 C2 H2B 109.5
H2A C2 H2B 109.5
C1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
C11 C12 H12 180.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N2 C3 1.3205(15)
N2 C7 1.3620(16)
O1 C1 1.2235(16)
C8 C9 1.3596(18)
C8 C6 1.4089(18)
C8 H8 0.9300
N3 C10 1.3286(16)
N3 C7 1.3566(15)
C11 C12 1.1855(18)
C11 C10 1.4428(17)
C7 C6 1.4139(17)
N1 C1 1.3735(16)
N1 C3 1.3901(16)
N1 H1 0.891(16)
C6 C5 1.4117(17)
C4 C5 1.3557(18)
C4 C3 1.4270(17)
C4 H4 0.9300
C5 H5 0.9300
C10 C9 1.4140(18)
C1 C2 1.4982(18)
C9 H9 0.9300
C2 H2A 0.9600
C2 H2B 0.9600
C2 H2C 0.9600
C12 H12 0.9300
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
C10 N3 C7 N2 178.38(11)
C10 N3 C7 C6 -1.48(18)
C3 N2 C7 N3 -179.87(10)
C3 N2 C7 C6 -0.01(18)
C9 C8 C6 C5 -178.17(12)
C9 C8 C6 C7 1.34(19)
N3 C7 C6 C8 -0.26(19)
N2 C7 C6 C8 179.89(11)
N3 C7 C6 C5 179.28(11)
N2 C7 C6 C5 -0.57(18)
C3 C4 C5 C6 0.78(19)
C8 C6 C5 C4 179.65(12)
C7 C6 C5 C4 0.14(19)
C7 N2 C3 N1 -177.17(10)
C7 N2 C3 C4 1.03(18)
C1 N1 C3 N2 -169.36(12)
C1 N1 C3 C4 12.4(2)
C5 C4 C3 N2 -1.43(19)
C5 C4 C3 N1 176.59(12)
C7 N3 C10 C9 2.23(19)
C7 N3 C10 C11 -176.73(11)
C3 N1 C1 O1 -1.4(2)
C3 N1 C1 C2 178.74(12)
C6 C8 C9 C10 -0.68(19)
N3 C10 C9 C8 -1.2(2)
C11 C10 C9 C8 177.76(12)
