#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/63/1516348.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_1516348
loop_
_publ_author_name
'Nelyubina, Yulia V.'
'Antipin, Mikhail Yu'
'Lyssenko, Konstantin A.'
_publ_section_title
;
 Hydrogen bonds between zwitterions: intermediate between classical and
 charge-assisted ones. A case study.
;
_journal_issue                   15
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              3615
_journal_page_last               3620
_journal_paper_doi               10.1021/jp809898g
_journal_volume                  113
_journal_year                    2009
_chemical_absolute_configuration unknown
_chemical_formula_moiety         'C9 H9 N O4'
_chemical_formula_sum            'C9 H9 N O4'
_chemical_formula_weight         195.17
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6786(2)
_cell_length_b                   7.7348(2)
_cell_length_c                   14.8561(4)
_cell_measurement_reflns_used    548
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_cell_volume                     882.34(4)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_publication_material  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_structure_refinement  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_structure_solution    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0145
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            86562
_diffrn_reflns_theta_full        52.49
_diffrn_reflns_theta_max         52.49
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         5685
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0298
_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)+(0.0636P)²+0.0068P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0836
_reflns_number_gt                5287
_reflns_number_total             5685
_reflns_threshold_expression     I>2/s(I)
_cod_data_source_file            jp809898g_si_001.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/retrospective/ACS/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 
;
_cod_database_code               1516348
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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
O1 O 0.18810(5) 0.08449(4) 0.91621(3) 0.01682(5) Uani 1 1 d
O2 O -0.09841(5) 0.14237(5) 0.90916(2) 0.01488(5) Uani 1 1 d
O3 O 0.05355(6) 0.71770(5) 0.83147(2) 0.01691(5) Uani 1 1 d
O4 O 0.12695(6) 0.78374(4) 0.97365(3) 0.01841(6) Uani 1 1 d
N1 N 0.27087(4) 0.38051(4) 0.824670(19) 0.01002(4) Uani 1 1 d
C1 C 0.09378(5) 0.36336(5) 0.86386(2) 0.00997(4) Uani 1 1 d
C2 C 0.06762(5) 0.49101(5) 0.94113(3) 0.01142(5) Uani 1 1 d
C3 C 0.05755(5) 0.17830(5) 0.89832(2) 0.01095(4) Uani 1 1 d
C4 C 0.08187(5) 0.67668(5) 0.90954(3) 0.01180(5) Uani 1 1 d
C5 C 0.28780(6) 0.40223(7) 0.73504(3) 0.01535(6) Uani 1 1 d
C6 C 0.45159(7) 0.41215(10) 0.69676(3) 0.02152(9) Uani 1 1 d
C7 C 0.59852(6) 0.40019(9) 0.75093(4) 0.02007(8) Uani 1 1 d
C8 C 0.57728(6) 0.37873(9) 0.84321(4) 0.01921(8) Uani 1 1 d
C9 C 0.41167(5) 0.36955(7) 0.87882(3) 0.01501(6) Uani 1 1 d
H4O H 0.145(2) 0.891(3) 0.9464(11) 0.036(4) Uiso 1 1 d
H1 H 0.0185(18) 0.3885(19) 0.8183(8) 0.019(3) Uiso 1 1 d
H2A H 0.157(2) 0.467(2) 0.9918(10) 0.026(3) Uiso 1 1 d
H2B H -0.055(2) 0.471(2) 0.9677(10) 0.029(3) Uiso 1 1 d
H5 H 0.186(2) 0.408(2) 0.7062(10) 0.025(3) Uiso 1 1 d
H6 H 0.471(3) 0.425(3) 0.6320(11) 0.040(4) Uiso 1 1 d
H7 H 0.717(2) 0.416(2) 0.7243(8) 0.021(3) Uiso 1 1 d
H8 H 0.678(3) 0.365(3) 0.8809(11) 0.042(4) Uiso 1 1 d
H9 H 0.390(2) 0.354(2) 0.9350(10) 0.029(3) Uiso 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 0.01567(11) 0.00936(9) 0.02544(14) 0.00260(9) 0.00054(10) 0.00102(8)
O2 0.01328(9) 0.01546(10) 0.01591(10) 0.00163(8) 0.00129(8) -0.00362(8)
O3 0.02395(14) 0.01339(10) 0.01338(10) 0.00302(8) -0.00126(10) 0.00146(10)
O4 0.02956(18) 0.00946(9) 0.01621(11) -0.00034(8) -0.00324(11) -0.00163(10)
N1 0.01042(8) 0.01074(8) 0.00888(8) 0.00104(6) 0.00029(6) 0.00016(7)
C1 0.01038(9) 0.00956(9) 0.00998(9) 0.00026(7) 0.00029(7) -0.00015(8)
C2 0.01417(11) 0.00894(9) 0.01114(10) 0.00034(7) 0.00173(8) 0.00011(9)
C3 0.01292(11) 0.00908(9) 0.01087(10) -0.00065(7) 0.00093(8) -0.00116(8)
C4 0.01365(11) 0.00910(9) 0.01265(10) 0.00092(8) 0.00051(9) 0.00076(8)
C5 0.01435(12) 0.02240(16) 0.00929(10) 0.00242(10) 0.00056(9) 0.00014(12)
C6 0.01781(16) 0.0345(3) 0.01223(13) 0.00400(15) 0.00450(12) 0.00117(17)
C7 0.01380(13) 0.0277(2) 0.01872(16) 0.00398(14) 0.00528(12) 0.00227(14)
C8 0.01118(12) 0.0289(2) 0.01750(14) 0.00471(15) 0.00038(10) 0.00122(13)
C9 0.01118(11) 0.02244(16) 0.01142(10) 0.00312(11) -0.00079(9) 0.00032(11)
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
C4 O4 H4O 106.7(10)
C5 N1 C9 121.26(3)
C5 N1 C1 119.12(3)
C9 N1 C1 119.60(3)
N1 C1 C2 110.93(3)
N1 C1 C3 112.17(3)
C2 C1 C3 109.04(3)
N1 C1 H1 105.7(9)
C2 C1 H1 109.7(9)
C3 C1 H1 109.3(9)
C4 C2 C1 111.74(3)
C4 C2 H2A 110.5(9)
C1 C2 H2A 109.9(8)
C4 C2 H2B 108.9(9)
C1 C2 H2B 108.2(9)
H2A C2 H2B 107.5(12)
O2 C3 O1 127.53(4)
O2 C3 C1 115.12(4)
O1 C3 C1 117.26(3)
O3 C4 O4 125.00(4)
O3 C4 C2 121.84(4)
O4 C4 C2 113.16(3)
N1 C5 C6 120.06(4)
N1 C5 H5 113.3(10)
C6 C5 H5 126.6(10)
C5 C6 C7 119.80(4)
C5 C6 H6 123.2(11)
C7 C6 H6 117.0(11)
C6 C7 C8 118.94(4)
C6 C7 H7 120.2(7)
C8 C7 H7 120.7(7)
C9 C8 C7 119.51(4)
C9 C8 H8 120.7(10)
C7 C8 H8 119.7(10)
N1 C9 C8 120.43(4)
N1 C9 H9 115.6(11)
C8 C9 H9 124.0(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.2657(5)
O2 C3 1.2399(5)
O3 C4 1.2218(5)
O4 C4 1.3088(5)
O4 H4O 0.94(2)
N1 C5 1.3483(5)
N1 C9 1.3503(5)
N1 C1 1.4852(5)
C1 C2 1.5274(5)
C1 C3 1.5454(5)
C1 H1 0.911(13)
C2 C4 1.5148(5)
C2 H2A 1.036(15)
C2 H2B 1.034(16)
C5 C6 1.3824(7)
C5 H5 0.891(15)
C6 C7 1.3889(8)
C6 H6 0.978(17)
C7 C8 1.3906(7)
C7 H7 1.003(15)
C8 C9 1.3791(6)
C8 H8 0.959(19)
C9 H9 0.860(14)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O4 H4O O1 1_565 0.93(2) 1.60(2) 2.5219(5) 170.2(16)
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
C5 N1 C1 C2 -127.83(4)
C9 N1 C1 C2 53.91(5)
C5 N1 C1 C3 109.96(4)
C9 N1 C1 C3 -68.29(5)
N1 C1 C2 C4 62.20(4)
C3 C1 C2 C4 -173.79(3)
N1 C1 C3 O2 -161.49(3)
C2 C1 C3 O2 75.23(4)
N1 C1 C3 O1 21.78(5)
C2 C1 C3 O1 -101.50(4)
C1 C2 C4 O3 24.61(6)
C1 C2 C4 O4 -155.25(4)
C9 N1 C5 C6 0.59(7)
C1 N1 C5 C6 -177.64(5)
N1 C5 C6 C7 -0.19(9)
C5 C6 C7 C8 -0.14(10)
C6 C7 C8 C9 0.10(10)
C5 N1 C9 C8 -0.63(7)
C1 N1 C9 C8 177.58(5)
C7 C8 C9 N1 0.28(9)
