#------------------------------------------------------------------------------
#$Date: 2020-06-05 12:45:09 +0300 (Fri, 05 Jun 2020) $
#$Revision: 252693 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/64/7126421.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_7126421
loop_
_publ_author_name
'Fueyo-González, Francisco'
'Garcia-Fernandez, Emilio'
'Martínez, David'
'Infantes, Lourdes'
'Orte, Angel'
'González-Vera, Juan A'
'Herranz, Rosario'
_publ_section_title
;
 Smart lanthanide antennas for sensing water.
;
_journal_issue                   41
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              5484
_journal_page_last               5487
_journal_paper_doi               10.1039/d0cc01725f
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C14 H13 N O4'
_chemical_formula_sum            'C14 H13 N O4'
_chemical_formula_weight         259.25
_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
_audit_creation_date             2020-01-24
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-29 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                102.100(4)
_cell_angle_beta                 92.658(4)
_cell_angle_gamma                101.463(4)
_cell_formula_units_Z            2
_cell_length_a                   7.1411(5)
_cell_length_b                   7.8726(5)
_cell_length_c                   10.6572(6)
_cell_measurement_reflns_used    1991
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      65.16
_cell_measurement_theta_min      4.26
_cell_volume                     571.71(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      119.99
_diffrn_measured_fraction_theta_full 0.925
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.925
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4613
_diffrn_reflns_point_group_measured_fraction_full 0.925
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        66.413
_diffrn_reflns_theta_max         66.413
_diffrn_reflns_theta_min         4.261
_exptl_absorpt_coefficient_mu    0.929
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_correction_T_min  0.6480
_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            colourless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_description       Prism
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         1865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0389
_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)+(0.0725P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1003
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1543
_reflns_number_total             1865
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc01725f2.cif
_cod_data_source_block           fjf190_mf
_cod_depositor_comments
'Adding full bibliography for 7126421--7126424.cif.'
_cod_database_code               7126421
_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.
;
_shelx_estimated_absorpt_t_max   0.946
_shelx_estimated_absorpt_t_min   0.897
_olex2_refinement_description
;
;
_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
O2 O 0.05360(13) -0.02683(13) -0.15512(9) 0.0229(3) Uani 1 1 d . . . . .
O3A O 0.27565(16) -0.02688(14) -0.37494(10) 0.0298(3) Uani 1 1 d . . . . .
O3B O 0.21123(14) 0.20069(13) -0.45286(9) 0.0241(3) Uani 1 1 d . . . . .
O8 O 0.15037(13) 0.43698(13) 0.24342(9) 0.0230(3) Uani 1 1 d . . . . .
N1 N 0.13006(15) 0.23566(16) -0.00847(11) 0.0181(3) Uani 1 1 d . . . . .
H1 H 0.071(3) 0.174(3) 0.0493(17) 0.036(5) Uiso 1 1 d . . . . .
C2 C 0.12642(18) 0.13394(18) -0.13157(13) 0.0187(3) Uani 1 1 d . . . . .
C3 C 0.20662(18) 0.22642(19) -0.23054(13) 0.0182(3) Uani 1 1 d . . . . .
C3A C 0.26749(17) 0.40713(18) -0.20066(13) 0.0179(3) Uani 1 1 d . . . . .
C3B C 0.23307(18) 0.11656(18) -0.35736(13) 0.0193(3) Uani 1 1 d . . . . .
C3C C 0.2500(2) 0.1096(2) -0.57892(14) 0.0271(4) Uani 1 1 d . . . . .
H3CA H 0.176(3) -0.014(3) -0.5965(18) 0.037(5) Uiso 1 1 d . . . . .
H3CB H 0.207(3) 0.169(3) -0.6400(19) 0.048(5) Uiso 1 1 d . . . . .
H3CC H 0.388(3) 0.108(3) -0.5810(18) 0.041(5) Uiso 1 1 d . . . . .
C4 C 0.34704(19) 0.54199(18) -0.27703(13) 0.0199(3) Uani 1 1 d . . . . .
H4A H 0.250(2) 0.544(2) -0.3429(15) 0.022(4) Uiso 1 1 d . . . . .
H4B H 0.453(2) 0.511(2) -0.3260(16) 0.029(4) Uiso 1 1 d . . . . .
C5 C 0.40728(19) 0.72315(18) -0.17832(13) 0.0210(3) Uani 1 1 d . . . . .
H5B H 0.341(2) 0.811(2) -0.2051(16) 0.028(4) Uiso 1 1 d . . . . .
H5A H 0.545(3) 0.770(2) -0.1714(16) 0.027(4) Uiso 1 1 d . . . . .
C5A C 0.34607(18) 0.68354(18) -0.05231(14) 0.0192(3) Uani 1 1 d . . . . .
C6 C 0.35707(19) 0.78650(19) 0.07024(14) 0.0213(3) Uani 1 1 d . . . . .
H6 H 0.411(2) 0.910(2) 0.0885(15) 0.022(4) Uiso 1 1 d . . . . .
C7 C 0.29092(19) 0.70522(19) 0.16982(13) 0.0215(3) Uani 1 1 d . . . . .
H7 H 0.301(2) 0.777(2) 0.2557(17) 0.027(4) Uiso 1 1 d . . . . .
C8 C 0.21407(18) 0.52422(19) 0.15031(13) 0.0193(3) Uani 1 1 d . . . . .
C8A C 0.1611(2) 0.5412(2) 0.37151(13) 0.0244(3) Uani 1 1 d . . . . .
H8AA H 0.079(2) 0.630(2) 0.3763(16) 0.027(4) Uiso 1 1 d . . . . .
H8AB H 0.291(2) 0.600(2) 0.4057(15) 0.023(4) Uiso 1 1 d . . . . .
H8AC H 0.109(2) 0.456(2) 0.4219(17) 0.030(4) Uiso 1 1 d . . . . .
C9A C 0.20109(17) 0.41744(18) 0.02474(13) 0.0176(3) Uani 1 1 d . . . . .
C9B C 0.26684(17) 0.50126(18) -0.07126(13) 0.0178(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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C3B O3B C3C 115.10(11) . . ?
C8 O8 C8A 117.22(11) . . ?
C2 N1 H1 114.6(11) . . ?
C2 N1 C9A 123.35(13) . . ?
C9A N1 H1 121.9(11) . . ?
O2 C2 N1 119.63(13) . . ?
O2 C2 C3 123.03(13) . . ?
N1 C2 C3 117.32(12) . . ?
C2 C3 C3B 118.13(12) . . ?
C3A C3 C2 119.79(13) . . ?
C3A C3 C3B 121.88(13) . . ?
C3 C3A C4 133.75(13) . . ?
C3 C3A C9B 118.94(14) . . ?
C9B C3A C4 107.28(12) . . ?
O3A C3B O3B 122.92(13) . . ?
O3A C3B C3 125.79(13) . . ?
O3B C3B C3 111.24(12) . . ?
O3B C3C H3CA 108.3(11) . . ?
O3B C3C H3CB 107.2(12) . . ?
O3B C3C H3CC 110.7(11) . . ?
H3CA C3C H3CB 109.7(16) . . ?
H3CA C3C H3CC 108.7(15) . . ?
H3CB C3C H3CC 112.3(16) . . ?
C3A C4 H4A 109.8(9) . . ?
C3A C4 H4B 112.9(10) . . ?
C3A C4 C5 106.06(11) . . ?
H4A C4 H4B 103.8(13) . . ?
C5 C4 H4A 111.9(10) . . ?
C5 C4 H4B 112.6(10) . . ?
C4 C5 H5B 109.6(9) . . ?
C4 C5 H5A 111.7(10) . . ?
H5B C5 H5A 108.8(13) . . ?
C5A C5 C4 104.67(11) . . ?
C5A C5 H5B 111.6(10) . . ?
C5A C5 H5A 110.4(10) . . ?
C6 C5A C5 133.34(13) . . ?
C6 C5A C9B 117.69(14) . . ?
C9B C5A C5 108.96(12) . . ?
C5A C6 H6 121.1(10) . . ?
C5A C6 C7 119.02(13) . . ?
C7 C6 H6 119.9(10) . . ?
C6 C7 H7 119.1(11) . . ?
C8 C7 C6 122.88(13) . . ?
C8 C7 H7 118.0(11) . . ?
O8 C8 C7 125.64(13) . . ?
O8 C8 C9A 115.78(12) . . ?
C7 C8 C9A 118.58(14) . . ?
O8 C8A H8AA 111.2(10) . . ?
O8 C8A H8AB 112.9(10) . . ?
O8 C8A H8AC 104.3(10) . . ?
H8AA C8A H8AB 109.7(13) . . ?
H8AA C8A H8AC 108.7(14) . . ?
H8AB C8A H8AC 109.9(14) . . ?
N1 C9A C8 124.86(14) . . ?
C9B C9A N1 117.93(13) . . ?
C9B C9A C8 117.20(13) . . ?
C5A C9B C3A 112.86(13) . . ?
C9A C9B C3A 122.46(13) . . ?
C9A C9B C5A 124.63(13) . . ?
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
O2 C2 1.2362(17) . ?
O3A C3B 1.2066(17) . ?
O3B C3B 1.3446(17) . ?
O3B C3C 1.4509(17) . ?
O8 C8 1.3662(17) . ?
O8 C8A 1.4275(16) . ?
N1 H1 0.93(2) . ?
N1 C2 1.3825(18) . ?
N1 C9A 1.3831(18) . ?
C2 C3 1.477(2) . ?
C3 C3A 1.366(2) . ?
C3 C3B 1.4862(19) . ?
C3A C4 1.509(2) . ?
C3A C9B 1.4228(19) . ?
C3C H3CA 0.989(19) . ?
C3C H3CB 0.95(2) . ?
C3C H3CC 0.99(2) . ?
C4 H4A 0.969(15) . ?
C4 H4B 0.983(17) . ?
C4 C5 1.553(2) . ?
C5 H5B 0.992(17) . ?
C5 H5A 0.975(17) . ?
C5 C5A 1.506(2) . ?
C5A C6 1.375(2) . ?
C5A C9B 1.4019(19) . ?
C6 H6 0.946(16) . ?
C6 C7 1.404(2) . ?
C7 H7 0.959(18) . ?
C7 C8 1.389(2) . ?
C8 C9A 1.4114(19) . ?
C8A H8AA 0.993(17) . ?
C8A H8AB 0.965(17) . ?
C8A H8AC 0.976(19) . ?
C9A C9B 1.381(2) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C2 C3 C3A 173.52(12) . . . . ?
O2 C2 C3 C3B -11.44(17) . . . . ?
O8 C8 C9A N1 -0.02(18) . . . . ?
O8 C8 C9A C9B -179.11(10) . . . . ?
N1 C2 C3 C3A -4.72(17) . . . . ?
N1 C2 C3 C3B 170.32(11) . . . . ?
N1 C9A C9B C3A -1.37(18) . . . . ?
N1 C9A C9B C5A -178.72(11) . . . . ?
C2 N1 C9A C8 -177.34(11) . . . . ?
C2 N1 C9A C9B 1.74(18) . . . . ?
C2 C3 C3A C4 -177.08(11) . . . . ?
C2 C3 C3A C9B 5.13(18) . . . . ?
C2 C3 C3B O3A -33.88(18) . . . . ?
C2 C3 C3B O3B 148.72(12) . . . . ?
C3 C3A C4 C5 -173.94(13) . . . . ?
C3 C3A C9B C5A 175.50(11) . . . . ?
C3 C3A C9B C9A -2.13(19) . . . . ?
C3A C3 C3B O3A 141.05(15) . . . . ?
C3A C3 C3B O3B -36.35(16) . . . . ?
C3A C4 C5 C5A -3.76(12) . . . . ?
C3B C3 C3A C4 8.1(2) . . . . ?
C3B C3 C3A C9B -169.72(11) . . . . ?
C3C O3B C3B O3A -2.3(2) . . . . ?
C3C O3B C3B C3 175.18(11) . . . . ?
C4 C3A C9B C5A -2.83(14) . . . . ?
C4 C3A C9B C9A 179.54(10) . . . . ?
C4 C5 C5A C6 -179.38(13) . . . . ?
C4 C5 C5A C9B 2.20(13) . . . . ?
C5 C5A C6 C7 -177.75(12) . . . . ?
C5 C5A C9B C3A 0.34(15) . . . . ?
C5 C5A C9B C9A 177.91(11) . . . . ?
C5A C6 C7 C8 -0.05(19) . . . . ?
C6 C5A C9B C3A -178.36(10) . . . . ?
C6 C5A C9B C9A -0.79(19) . . . . ?
C6 C7 C8 O8 178.84(11) . . . . ?
C6 C7 C8 C9A -0.31(19) . . . . ?
C7 C8 C9A N1 179.21(11) . . . . ?
C7 C8 C9A C9B 0.12(17) . . . . ?
C8 C9A C9B C3A 177.79(11) . . . . ?
C8 C9A C9B C5A 0.44(18) . . . . ?
C8A O8 C8 C7 0.96(18) . . . . ?
C8A O8 C8 C9A -179.87(10) . . . . ?
C9A N1 C2 O2 -177.10(11) . . . . ?
C9A N1 C2 C3 1.20(18) . . . . ?
C9B C3A C4 C5 4.03(13) . . . . ?
C9B C5A C6 C7 0.56(18) . . . . ?
