#------------------------------------------------------------------------------
#$Date: 2022-09-29 03:45:47 +0300 (Thu, 29 Sep 2022) $
#$Revision: 278261 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/89/7158900.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_7158900
loop_
_publ_author_name
'Sánchez Santos, Estela'
'Garrido-González, José J.'
'Fuentes de Arriba, Angel L.'
'Rodríguez-Sahagún, Ligzajaya'
'Habib, Asmaa'
'Sanz, Francisca'
'Martin del Valle, Eva'
'Rodriguez Moran, Joaquin'
'Alcazar, Victoria'
_publ_section_title
;
 Tryptophan association in water driven by charge-transfer interactions
 with electron-deficient aromatic haptens
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01650H
_journal_year                    2022
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C11 H12 N2 O2, C7 H4 N2 O6, C H4 O'
_chemical_formula_sum            'C19 H20 N4 O9'
_chemical_formula_weight         448.39
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2022-06-15 deposited with the CCDC.	2022-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.214(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.2094(4)
_cell_length_b                   7.5386(3)
_cell_length_c                   19.1587(8)
_cell_measurement_reflns_used    2715
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      64.22
_cell_measurement_theta_min      2.33
_cell_volume                     1030.57(8)
_computing_cell_refinement       'SAINT (Bruker 2006)'
_computing_data_collection       'APEX 2 (Bruker 2006)'
_computing_data_reduction        'SAINT (Bruker 2006)'
_computing_molecular_graphics    'Mercury 4.0.0 (Macrae et al, 2008)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.946
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7296
_diffrn_reflns_theta_full        66.72
_diffrn_reflns_theta_max         66.72
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.999
_exptl_absorpt_correction_T_max  0.905
_exptl_absorpt_correction_T_min  0.866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         2586
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0528
_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)+(0.0993P)²+0.3879P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1483
_refine_ls_wR_factor_ref         0.1521
_reflns_number_gt                2369
_reflns_number_total             2586
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2ob01650h2.cif
_cod_data_source_block           invertida
_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/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_Hall     P2yb
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7158900
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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 0.0635(5) 0.7551(7) 0.24932(19) 0.0463(10) Uani 1 1 d . . .
H1 H 0.1799 0.7029 0.2630 0.056 Uiso 1 1 calc R . .
N1 N -0.0062(5) 0.8090(5) 0.18192(15) 0.0507(9) Uani 1 1 d . . .
H1N H 0.0517 0.7995 0.1458 0.061 Uiso 1 1 calc R . .
C2 C -0.1791(5) 0.8789(6) 0.18110(18) 0.0431(9) Uani 1 1 d . . .
C3 C -0.3068(6) 0.9460(7) 0.1257(2) 0.0529(11) Uani 1 1 d . . .
H3 H -0.2780 0.9488 0.0799 0.063 Uiso 1 1 calc R . .
C4 C -0.4742(7) 1.0071(7) 0.1404(2) 0.0602(12) Uani 1 1 d . . .
H4 H -0.5610 1.0519 0.1041 0.072 Uiso 1 1 calc R . .
C5 C -0.5196(6) 1.0040(7) 0.2104(2) 0.0602(12) Uani 1 1 d . . .
H5 H -0.6339 1.0493 0.2193 0.072 Uiso 1 1 calc R . .
C6 C -0.3966(5) 0.9349(7) 0.2647(2) 0.0484(10) Uani 1 1 d . . .
H6 H -0.4278 0.9308 0.3102 0.058 Uiso 1 1 calc R . .
C7 C -0.2239(5) 0.8707(6) 0.25100(17) 0.0400(9) Uani 1 1 d . . .
C8 C -0.0666(5) 0.7911(6) 0.29282(17) 0.0393(9) Uani 1 1 d . . .
C9 C -0.0505(5) 0.7452(6) 0.36993(17) 0.0406(9) Uani 1 1 d . . .
H9A H 0.0532 0.6636 0.3817 0.049 Uiso 1 1 calc R . .
H9B H -0.1640 0.6845 0.3783 0.049 Uiso 1 1 calc R . .
C10 C -0.0202(5) 0.9059(5) 0.41916(17) 0.0363(8) Uani 1 1 d . . .
H10 H -0.1212 0.9913 0.4052 0.044 Uiso 1 1 calc R . .
C11 C -0.0279(5) 0.8497(6) 0.49463(17) 0.0396(9) Uani 1 1 d . . .
N2 N 0.1618(4) 0.9932(5) 0.41259(15) 0.0408(8) Uani 1 1 d . . .
H2A H 0.2541 0.9143 0.4213 0.061 Uiso 1 1 calc R . .
H2B H 0.1813 1.0818 0.4434 0.061 Uiso 1 1 calc R . .
H2C H 0.1587 1.0355 0.3691 0.061 Uiso 1 1 calc R . .
C12 C 0.3266(5) 0.9358(6) 0.80831(18) 0.0424(9) Uani 1 1 d . . .
H12 H 0.4040 0.9590 0.7745 0.051 Uiso 1 1 calc R . .
O1 O 0.1216(4) 0.8489(5) 0.53662(12) 0.0550(8) Uani 1 1 d . . .
O2 O -0.1839(4) 0.7990(5) 0.50792(13) 0.0536(8) Uani 1 1 d . . .
C13 C 0.3828(5) 0.9785(6) 0.87849(19) 0.0410(9) Uani 1 1 d . . .
C14 C 0.2773(6) 0.9425(6) 0.93107(18) 0.0433(9) Uani 1 1 d . . .
H14 H 0.3191 0.9695 0.9780 0.052 Uiso 1 1 calc R . .
C15 C 0.1036(5) 0.8628(6) 0.90976(17) 0.0411(8) Uani 1 1 d . . .
C16 C 0.0400(5) 0.8202(6) 0.84130(19) 0.0418(9) Uani 1 1 d . . .
H16 H -0.0766 0.7670 0.8293 0.050 Uiso 1 1 calc R . .
C17 C 0.1523(5) 0.8575(6) 0.78947(18) 0.0406(8) Uani 1 1 d . . .
C18 C 0.0794(6) 0.8137(6) 0.71498(19) 0.0456(10) Uani 1 1 d . . .
O3 O 0.1978(4) 0.8481(5) 0.67117(13) 0.0518(7) Uani 1 1 d . . .
H3A H 0.1406 0.8596 0.6312 0.078 Uiso 1 1 calc R . .
O4 O -0.0759(4) 0.7493(5) 0.69830(15) 0.0631(9) Uani 1 1 d . . .
N3 N -0.0131(5) 0.8214(6) 0.96470(17) 0.0551(10) Uani 1 1 d . . .
O5 O -0.1645(5) 0.7510(7) 0.94692(18) 0.0850(12) Uani 1 1 d . . .
O6 O 0.0457(5) 0.8658(7) 1.02535(14) 0.0833(14) Uani 1 1 d . . .
N4 N 0.5670(4) 1.0607(6) 0.89887(17) 0.0502(9) Uani 1 1 d . . .
O7 O 0.6090(5) 1.1099(6) 0.95982(16) 0.0726(11) Uani 1 1 d . . .
O8 O 0.6695(4) 1.0782(6) 0.85359(16) 0.0721(11) Uani 1 1 d . . .
O9 O -0.5289(5) 0.7626(7) 0.42540(19) 0.0804(10) Uiso 1 1 d D . .
H9 H -0.4946 0.7717 0.4679 0.121 Uiso 1 1 calc R . .
C19 C -0.5482(14) 0.5716(15) 0.4059(5) 0.153(4) Uiso 1 1 d D . .
H19A H -0.4347 0.5101 0.4239 0.230 Uiso 1 1 calc R . .
H19B H -0.5711 0.5605 0.3555 0.230 Uiso 1 1 calc R . .
H19C H -0.6510 0.5212 0.4259 0.230 Uiso 1 1 calc R . .
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
C8 C1 N1 108.8(3) . . ?
C8 C1 H1 125.6 . . ?
N1 C1 H1 125.6 . . ?
C2 N1 C1 109.7(3) . . ?
C2 N1 H1N 125.1 . . ?
C1 N1 H1N 125.1 . . ?
N1 C2 C3 131.1(3) . . ?
N1 C2 C7 107.8(3) . . ?
C3 C2 C7 121.1(4) . . ?
C4 C3 C2 118.3(4) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 121.3(4) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 120.7(4) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 119.1(4) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C6 C7 C2 119.4(3) . . ?
C6 C7 C8 134.5(3) . . ?
C2 C7 C8 106.1(3) . . ?
C1 C8 C7 107.5(3) . . ?
C1 C8 C9 126.1(3) . . ?
C7 C8 C9 126.3(3) . . ?
C8 C9 C10 114.0(3) . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.6 . . ?
N2 C10 C11 110.9(3) . . ?
N2 C10 C9 110.3(3) . . ?
C11 C10 C9 110.2(3) . . ?
N2 C10 H10 108.5 . . ?
C11 C10 H10 108.5 . . ?
C9 C10 H10 108.5 . . ?
O2 C11 O1 125.9(3) . . ?
O2 C11 C10 115.9(3) . . ?
O1 C11 C10 118.0(3) . . ?
C10 N2 H2A 109.5 . . ?
C10 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C10 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C13 C12 C17 118.7(3) . . ?
C13 C12 H12 120.7 . . ?
C17 C12 H12 120.7 . . ?
C14 C13 C12 123.3(4) . . ?
C14 C13 N4 117.6(3) . . ?
C12 C13 N4 119.0(3) . . ?
C13 C14 C15 116.0(3) . . ?
C13 C14 H14 122.0 . . ?
C15 C14 H14 122.0 . . ?
C16 C15 C14 123.1(3) . . ?
C16 C15 N3 119.3(4) . . ?
C14 C15 N3 117.6(3) . . ?
C15 C16 C17 119.1(4) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C12 C17 C16 119.7(3) . . ?
C12 C17 C18 121.8(3) . . ?
C16 C17 C18 118.5(4) . . ?
O4 C18 O3 124.8(3) . . ?
O4 C18 C17 121.7(4) . . ?
O3 C18 C17 113.5(3) . . ?
C18 O3 H3A 109.5 . . ?
O5 N3 O6 124.0(3) . . ?
O5 N3 C15 118.3(3) . . ?
O6 N3 C15 117.7(4) . . ?
O7 N4 O8 123.5(4) . . ?
O7 N4 C13 118.3(3) . . ?
O8 N4 C13 118.2(3) . . ?
C19 O9 H9 109.5 . . ?
O9 C19 H19A 109.5 . . ?
O9 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O9 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
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 C8 1.367(5) . ?
C1 N1 1.378(5) . ?
C1 H1 0.9300 . ?
N1 C2 1.352(5) . ?
N1 H1N 0.8600 . ?
C2 C3 1.397(6) . ?
C2 C7 1.423(5) . ?
C3 C4 1.359(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.425(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.370(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.395(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.424(5) . ?
C8 C9 1.506(5) . ?
C9 C10 1.532(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.489(5) . ?
C10 C11 1.515(5) . ?
C10 H10 0.9800 . ?
C11 O2 1.248(5) . ?
C11 O1 1.250(4) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
C12 C13 1.386(5) . ?
C12 C17 1.389(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.373(5) . ?
C13 N4 1.467(5) . ?
C14 C15 1.397(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.364(5) . ?
C15 N3 1.472(5) . ?
C16 C17 1.397(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.486(5) . ?
C18 O4 1.220(5) . ?
C18 O3 1.306(5) . ?
O3 H3A 0.8200 . ?
N3 O5 1.217(5) . ?
N3 O6 1.225(4) . ?
N4 O7 1.221(4) . ?
N4 O8 1.224(4) . ?
O9 C19 1.489(12) . ?
O9 H9 0.8200 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
