#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/49/1514930.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_1514930
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         'C6 H7 N2 O, 0.5(C4 O4)'
_chemical_formula_sum            'C8 H7 N2 O3'
_chemical_formula_weight         179.16
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 101.972(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.047(6)
_cell_length_b                   8.368(2)
_cell_length_c                   9.364(2)
_cell_measurement_reflns_used    1423
_cell_measurement_temperature    199(2)
_cell_measurement_theta_max      25.16
_cell_measurement_theta_min      1.98
_cell_volume                     1613.3(7)
_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      199(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4877
_diffrn_reflns_theta_full        25.16
_diffrn_reflns_theta_max         25.16
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.9761
_exptl_absorpt_correction_T_min  0.9577
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.687
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1423
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.687
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1080P)²+2.0956P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1220
_reflns_number_gt                1137
_reflns_number_total             1423
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ay25090j.txt
_cod_data_source_block           bi119
_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_cell_volume        1613.2(7)
_cod_original_sg_symbol_Hall     '- C 2yc'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1514930
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.79802(7) 0.62349(16) 0.78827(16) 0.0561(4) Uani 1 1 d .
H1 H 0.8295 0.5701 0.8342 0.084 Uiso 1 1 calc R
O2 O 1.10817(6) 0.55090(17) 1.07104(18) 0.0606(5) Uani 1 1 d .
O3 O 1.01278(7) 0.23864(15) 1.06770(16) 0.0553(4) Uani 1 1 d .
N1 N 0.76210(7) 0.53059(19) 0.67830(16) 0.0454(4) Uani 1 1 d .
N2 N 0.59124(7) 0.56935(18) 0.26475(16) 0.0415(4) Uani 1 1 d .
H2 H 0.5662 0.6330 0.2025 0.050 Uiso 1 1 calc R
C8 C 1.00683(9) 0.3827(2) 1.03225(19) 0.0402(4) Uani 1 1 d .
C1 C 0.71768(9) 0.6134(2) 0.59836(19) 0.0424(5) Uani 1 1 d .
H1A H 0.7137 0.7240 0.6179 0.051 Uiso 1 1 calc R
C2 C 0.67287(8) 0.5387(2) 0.47693(18) 0.0375(4) Uani 1 1 d .
C3 C 0.63180(8) 0.6338(2) 0.3782(2) 0.0408(4) Uani 1 1 d .
H3 H 0.6325 0.7464 0.3913 0.049 Uiso 1 1 calc R
C4 C 0.58706(9) 0.4124(2) 0.2417(2) 0.0447(5) Uani 1 1 d .
H4 H 0.5577 0.3704 0.1594 0.054 Uiso 1 1 calc R
C5 C 0.66891(9) 0.3749(2) 0.4556(2) 0.0443(5) Uani 1 1 d .
H5 H 0.6961 0.3058 0.5221 0.053 Uiso 1 1 calc R
C6 C 0.62573(10) 0.3119(2) 0.3383(2) 0.0490(5) Uani 1 1 d .
H6 H 0.6227 0.1994 0.3243 0.059 Uiso 1 1 calc R
C7 C 1.04894(8) 0.5205(2) 1.03359(19) 0.0418(4) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0532(9) 0.0469(9) 0.0568(9) -0.0085(6) -0.0152(7) 0.0053(6)
O2 0.0357(7) 0.0481(8) 0.0858(11) 0.0090(7) -0.0156(7) -0.0016(6)
O3 0.0507(8) 0.0336(7) 0.0695(9) 0.0134(6) -0.0152(7) 0.0023(6)
N1 0.0422(9) 0.0461(9) 0.0432(9) -0.0034(7) -0.0022(7) 0.0018(7)
N2 0.0365(8) 0.0426(9) 0.0415(8) 0.0071(7) -0.0009(6) 0.0090(6)
C8 0.0401(9) 0.0320(9) 0.0412(10) 0.0031(7) -0.0082(8) 0.0035(7)
C1 0.0400(10) 0.0420(10) 0.0425(10) 0.0013(8) 0.0024(8) 0.0055(7)
C2 0.0340(9) 0.0419(10) 0.0363(9) 0.0034(7) 0.0066(7) 0.0065(7)
C3 0.0383(9) 0.0362(10) 0.0450(10) 0.0023(8) 0.0023(8) 0.0066(7)
C4 0.0418(10) 0.0478(11) 0.0426(10) -0.0007(8) 0.0043(8) 0.0018(8)
C5 0.0461(10) 0.0424(11) 0.0423(10) 0.0074(8) 0.0047(8) 0.0118(8)
C6 0.0568(12) 0.0370(10) 0.0511(11) 0.0008(8) 0.0059(9) 0.0036(8)
C7 0.0365(9) 0.0360(9) 0.0447(10) 0.0027(8) -0.0103(7) 0.0025(7)
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_3
N1 O1 H1 109.5 .
C1 N1 O1 110.65(16) .
C4 N2 C3 122.61(15) .
C4 N2 H2 118.7 .
C3 N2 H2 118.7 .
O3 C8 C7 137.40(17) .
O3 C8 C7 132.64(17) 5_767
C7 C8 C7 89.94(14) 5_767
N1 C1 C2 120.10(17) .
N1 C1 H1A 120.0 .
C2 C1 H1A 120.0 .
C3 C2 C5 117.60(16) .
C3 C2 C1 119.29(17) .
C5 C2 C1 123.11(16) .
N2 C3 C2 120.67(17) .
N2 C3 H3 119.7 .
C2 C3 H3 119.7 .
N2 C4 C6 119.21(17) .
N2 C4 H4 120.4 .
C6 C4 H4 120.4 .
C6 C5 C2 120.27(17) .
C6 C5 H5 119.9 .
C2 C5 H5 119.9 .
C4 C6 C5 119.60(19) .
C4 C6 H6 120.2 .
C5 C6 H6 120.2 .
O2 C7 C8 137.33(16) .
O2 C7 C8 132.60(17) 5_767
C8 C7 C8 90.06(14) 5_767
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 N1 1.3832(19) .
O1 H1 0.8400 .
O2 C7 1.249(2) .
O3 C8 1.250(2) .
N1 C1 1.275(2) .
N2 C4 1.331(2) .
N2 C3 1.331(2) .
N2 H2 0.8800 .
C8 C7 1.453(3) .
C8 C7 1.454(2) 5_767
C1 C2 1.459(3) .
C1 H1A 0.9500 .
C2 C3 1.380(2) .
C2 C5 1.385(3) .
C3 H3 0.9500 .
C4 C6 1.372(3) .
C4 H4 0.9500 .
C5 C6 1.377(3) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 C8 1.454(2) 5_767
