#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/49/1514927.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_1514927
loop_
_publ_author_name
'Ivanova, Bojidarka B.'
_publ_section_title
;
 Matrixes in UV-MALDI mass spectrometry -- crystals of organic salts
 versus co-crystals of neutral polyfunctional carboxylic acids
;
_journal_issue                   8
_journal_name_full               'Analytical Methods'
_journal_page_first              2247
_journal_paper_doi               10.1039/c2ay25090j
_journal_volume                  4
_journal_year                    2012
_chemical_formula_moiety         '(C4 H O4), (C12 H10 N O)'
_chemical_formula_sum            'C16 H11 N O5'
_chemical_formula_weight         297.26
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.033(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.7822(18)
_cell_length_b                   7.2392(9)
_cell_length_c                   12.5086(17)
_cell_measurement_reflns_used    2426
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.34
_cell_volume                     1373.5(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker GIS'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker APEX2'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -15
_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            8370
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.34
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_correction_T_min  0.7595
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2426
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.955
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0796P)²+0.3501P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1301
_reflns_number_gt                1825
_reflns_number_total             2426
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ay25090j.txt
_cod_data_source_block           scan_0m_p21_c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 


 Removing Professor Michael Spiteller's name from the authors' list as
 requested in the addendum
 http://www.rsc.org/suppdata/ay/c2/c2ay25090j/addition.htm

 Saulius Gra\<zulis
 2014-10-05

;
_cod_original_sg_symbol_H-M      P12(1)/c1
_cod_database_code               1514927
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O -0.04112(9) 1.0702(3) 0.11042(12) 0.0665(5) Uani 1 1 d .
O2 O -0.12145(10) 0.9494(3) 0.42761(12) 0.0630(5) Uani 1 1 d .
O3 O -0.22525(11) 0.9640(3) 0.16728(14) 0.0697(5) Uani 1 1 d .
O4 O 0.06119(10) 1.0691(3) 0.36507(13) 0.0703(5) Uani 1 1 d .
H4 H 0.0674 1.0647 0.4323 0.105 Uiso 1 1 calc R
O5 O 0.35982(10) 0.8350(2) 1.45370(11) 0.0600(5) Uani 1 1 d .
N1 N 0.16529(11) 0.9290(2) 1.08127(14) 0.0459(4) Uani 1 1 d .
H1 H 0.1208 0.9445 1.0241 0.055 Uiso 1 1 calc R
C1 C -0.06487(13) 1.0389(3) 0.19624(16) 0.0477(5) Uani 1 1 d .
C2 C -0.02142(13) 1.0358(3) 0.31189(17) 0.0465(5) Uani 1 1 d .
C3 C -0.09995(13) 0.9849(3) 0.34107(16) 0.0431(5) Uani 1 1 d .
C4 C -0.14910(14) 0.9885(3) 0.22120(17) 0.0462(5) Uani 1 1 d .
C5 C 0.16456(13) 1.0071(3) 1.17786(17) 0.0474(5) Uani 1 1 d .
H5 H 0.1165 1.0777 1.1824 0.057 Uiso 1 1 calc R
C6 C 0.23420(13) 0.9834(3) 1.26963(17) 0.0427(5) Uani 1 1 d .
H6 H 0.2333 1.0366 1.3370 0.051 Uiso 1 1 calc R
C7 C 0.30655(12) 0.8796(2) 1.26238(15) 0.0349(4) Uani 1 1 d .
C8 C 0.37970(13) 0.8458(2) 1.36670(15) 0.0384(4) Uani 1 1 d .
C9 C 0.47332(12) 0.8248(2) 1.36488(15) 0.0358(4) Uani 1 1 d .
C10 C 0.53155(14) 0.7427(3) 1.45583(17) 0.0478(5) Uani 1 1 d .
H10 H 0.5112 0.6985 1.5140 0.057 Uiso 1 1 calc R
C11 C 0.61982(15) 0.7261(3) 1.4608(2) 0.0591(6) Uani 1 1 d .
H11 H 0.6585 0.6698 1.5219 0.071 Uiso 1 1 calc R
C12 C 0.65048(14) 0.7928(3) 1.3753(2) 0.0573(6) Uani 1 1 d .
H12 H 0.7100 0.7830 1.3793 0.069 Uiso 1 1 calc R
C13 C 0.30505(12) 0.8012(2) 1.16065(16) 0.0388(4) Uani 1 1 d .
H13 H 0.3525 0.7313 1.1532 0.047 Uiso 1 1 calc R
C14 C 0.23328(13) 0.8275(3) 1.07144(16) 0.0443(5) Uani 1 1 d .
H14 H 0.2318 0.7742 1.0033 0.053 Uiso 1 1 calc R
C15 C 0.59351(13) 0.8737(3) 1.28428(19) 0.0497(5) Uani 1 1 d .
H15 H 0.6145 0.9175 1.2265 0.060 Uiso 1 1 calc R
C16 C 0.50484(13) 0.8904(2) 1.27822(16) 0.0407(5) Uani 1 1 d .
H16 H 0.4664 0.9453 1.2164 0.049 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 0.0033 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
C2 O4 H4 109.5
C14 N1 C5 121.62(18)
C14 N1 H1 119.2
C5 N1 H1 119.2
O1 C1 C2 134.59(19)
O1 C1 C4 136.0(2)
C2 C1 C4 89.45(16)
O4 C2 C1 130.27(18)
O4 C2 C3 136.56(19)
C1 C2 C3 93.17(17)
O2 C3 C2 137.3(2)
O2 C3 C4 133.48(18)
C2 C3 C4 89.18(15)
O3 C4 C1 136.0(2)
O3 C4 C3 135.77(19)
C1 C4 C3 88.20(16)
N1 C5 C6 120.11(18)
N1 C5 H5 119.9
C6 C5 H5 119.9
C5 C6 C7 119.90(18)
C5 C6 H6 120.0
C7 C6 H6 120.0
C13 C7 C6 118.32(18)
C13 C7 C8 122.94(16)
C6 C7 C8 118.58(16)
O5 C8 C9 120.58(18)
O5 C8 C7 117.46(16)
C9 C8 C7 121.96(15)
C10 C9 C16 119.13(18)
C10 C9 C8 117.83(17)
C16 C9 C8 122.99(17)
C9 C10 C11 120.5(2)
C9 C10 H10 119.8
C11 C10 H10 119.8
C12 C11 C10 120.0(2)
C12 C11 H11 120.0
C10 C11 H11 120.0
C15 C12 C11 120.3(2)
C15 C12 H12 119.9
C11 C12 H12 119.9
C14 C13 C7 119.51(17)
C14 C13 H13 120.2
C7 C13 H13 120.2
N1 C14 C13 120.53(18)
N1 C14 H14 119.7
C13 C14 H14 119.7
C12 C15 C16 120.2(2)
C12 C15 H15 119.9
C16 C15 H15 119.9
C15 C16 C9 119.96(19)
C15 C16 H16 120.0
C9 C16 H16 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.251(2)
O2 C3 1.247(2)
O3 C4 1.218(2)
O4 C2 1.312(2)
O4 H4 0.8200
O5 C8 1.215(2)
N1 C14 1.334(2)
N1 C5 1.337(3)
N1 H1 0.8600
C1 C2 1.420(3)
C1 C4 1.492(3)
C2 C3 1.434(3)
C3 C4 1.486(3)
C5 C6 1.363(3)
C5 H5 0.9300
C6 C7 1.391(3)
C6 H6 0.9300
C7 C13 1.387(2)
C7 C8 1.504(3)
C8 C9 1.492(3)
C9 C10 1.384(3)
C9 C16 1.395(2)
C10 C11 1.382(3)
C10 H10 0.9300
C11 C12 1.377(3)
C11 H11 0.9300
C12 C15 1.372(3)
C12 H12 0.9300
C13 C14 1.366(3)
C13 H13 0.9300
C14 H14 0.9300
C15 C16 1.386(3)
C15 H15 0.9300
C16 H16 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139042697
