#------------------------------------------------------------------------------
#$Date: 2015-06-05 08:07:32 +0300 (Fri, 05 Jun 2015) $
#$Revision: 138257 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/35/4123587.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_4123587
loop_
_publ_author_name
'Sigala, Paul A.'
'Ruben, Eliza A.'
'Liu, Corey W.'
'Piccoli, Paula M. B.'
'Hohenstein, Edward G.'
'Martínez, Todd J'
'Schultz, Arthur J.'
'Herschlag, Daniel'
_publ_section_title
;
 Determination of Hydrogen Bond Structure in Water versus Aprotic
 Environments To Test the Relationship Between Length and Stability.
;
_journal_issue                   17
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5730
_journal_page_last               5740
_journal_paper_doi               10.1021/ja512980h
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C12 H11 N3 O6'
_chemical_formula_sum            'C12 H11 N3 O6'
_chemical_formula_weight         293.24
_chemical_name_systematic
;
 2,4-dinitrophenol 4-methylpyridine-N-oxide
;
_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   geom
_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                   6.5577(8)
_cell_length_b                   7.6142(10)
_cell_length_c                   25.315(3)
_cell_measurement_reflns_used    3534
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.76
_cell_measurement_theta_min      3.12
_cell_volume                     1264.0(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_sigmaI/netI    0.0500
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            21207
_diffrn_reflns_theta_full        31.68
_diffrn_reflns_theta_max         31.68
_diffrn_reflns_theta_min         2.79
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.737502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.9(10)
_refine_ls_extinction_coef       0.0033(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4263
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0428
_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)+(0.0517P)²+0.0807P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1044
_reflns_number_gt                3131
_reflns_number_total             4263
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            978285.cif
_cod_data_source_block           p212121
_cod_depositor_comments
'Adding full bibliography for 4123587--4123590.cif.'
_cod_database_code               4123587
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
C1 C 0.4736(2) 0.0138(2) 0.08825(6) 0.0228(3) Uani 1 1 d
C2 C 0.3870(2) -0.0068(2) 0.13901(6) 0.0240(3) Uani 1 1 d
C3 C 0.1978(2) -0.0847(2) 0.14616(6) 0.0248(3) Uani 1 1 d
C4 C 0.0931(2) -0.1448(2) 0.10248(6) 0.0226(3) Uani 1 1 d
C5 C 0.1744(3) -0.1301(2) 0.05182(6) 0.0242(3) Uani 1 1 d
C6 C 0.3612(2) -0.0528(2) 0.04536(6) 0.0244(3) Uani 1 1 d
C7 C 0.3972(3) 0.4734(2) 0.09485(6) 0.0260(3) Uani 1 1 d
C8 C 0.3374(3) 0.4758(2) 0.14688(6) 0.0277(3) Uani 1 1 d
C9 C 0.1486(3) 0.4090(2) 0.16218(6) 0.0272(3) Uani 1 1 d
C10 C 0.0264(3) 0.3375(2) 0.12259(6) 0.0269(3) Uani 1 1 d
C11 C 0.0906(3) 0.3344(2) 0.07091(6) 0.0244(3) Uani 1 1 d
C12 C 0.0793(4) 0.4111(4) 0.21879(7) 0.0437(5) Uani 1 1 d
N1 N 0.4905(2) 0.0540(2) 0.18704(5) 0.0299(3) Uani 1 1 d
N2 N -0.1043(2) -0.22950(18) 0.10990(5) 0.0269(3) Uani 1 1 d
N3 N 0.27250(19) 0.40404(18) 0.05760(5) 0.0226(3) Uani 1 1 d
O1 O 0.65228(17) 0.09142(16) 0.08096(4) 0.0275(3) Uani 1 1 d
O2 O 0.4189(3) 0.0099(3) 0.22953(5) 0.0732(6) Uani 1 1 d
O3 O 0.6412(2) 0.14486(19) 0.18375(5) 0.0421(3) Uani 1 1 d
O4 O -0.18950(18) -0.28990(16) 0.07057(5) 0.0335(3) Uani 1 1 d
O5 O -0.1764(2) -0.23842(18) 0.15457(5) 0.0371(3) Uani 1 1 d
O6 O 0.33493(18) 0.40414(17) 0.00736(4) 0.0322(3) Uani 1 1 d
H3 H 0.149(3) -0.101(2) 0.1818(8) 0.029(5) Uiso 1 1 d
H5 H 0.103(3) -0.172(3) 0.0256(9) 0.042(6) Uiso 1 1 d
H6 H 0.420(3) -0.038(2) 0.0112(7) 0.026(5) Uiso 1 1 d
H7 H 0.532(3) 0.511(2) 0.0825(7) 0.022(4) Uiso 1 1 d
H8 H 0.427(3) 0.523(3) 0.1688(9) 0.046(6) Uiso 1 1 d
H10 H -0.101(3) 0.297(3) 0.1314(8) 0.045(6) Uiso 1 1 d
H11 H 0.023(3) 0.286(2) 0.0430(8) 0.029(5) Uiso 1 1 d
H12C H -0.062(5) 0.401(3) 0.2220(10) 0.065(8) Uiso 1 1 d
H12B H 0.137(6) 0.314(5) 0.2348(14) 0.121(14) Uiso 1 1 d
H12A H 0.133(5) 0.508(5) 0.2399(14) 0.116(12) Uiso 1 1 d
H13 H 0.691(3) 0.078(3) 0.0469(8) 0.038(5) Uiso 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 0.0033 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
O1 C1 C6 121.10(13)
O1 C1 C2 122.09(13)
C6 C1 C2 116.81(14)
C3 C2 C1 121.68(14)
C3 C2 N1 116.14(13)
C1 C2 N1 122.17(13)
C4 C3 C2 118.84(14)
C4 C3 H3 122.7(11)
C2 C3 H3 118.4(11)
C3 C4 C5 121.40(14)
C3 C4 N2 119.02(13)
C5 C4 N2 119.56(14)
C6 C5 C4 119.12(14)
C6 C5 H5 123.2(14)
C4 C5 H5 117.7(14)
C5 C6 C1 122.12(14)
C5 C6 H6 121.2(11)
C1 C6 H6 116.6(11)
N3 C7 C8 120.00(15)
N3 C7 H7 115.8(10)
C8 C7 H7 124.0(10)
C7 C8 C9 120.99(15)
C7 C8 H8 114.5(14)
C9 C8 H8 124.5(14)
C8 C9 C10 116.98(14)
C8 C9 C12 122.00(16)
C10 C9 C12 121.02(17)
C11 C10 C9 120.98(16)
C11 C10 H10 120.2(13)
C9 C10 H10 118.7(13)
N3 C11 C10 120.15(15)
N3 C11 H11 113.3(12)
C10 C11 H11 126.5(12)
C9 C12 H12C 112.4(15)
C9 C12 H12B 107(2)
H12C C12 H12B 108(3)
C9 C12 H12A 115(2)
H12C C12 H12A 112(3)
H12B C12 H12A 103(3)
O3 N1 O2 122.17(15)
O3 N1 C2 120.09(13)
O2 N1 C2 117.74(14)
O5 N2 O4 123.34(14)
O5 N2 C4 119.01(14)
O4 N2 C4 117.65(13)
O6 N3 C11 120.61(13)
O6 N3 C7 118.50(13)
C11 N3 C7 120.88(13)
C1 O1 H13 109.5(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.3252(19)
C1 C6 1.407(2)
C1 C2 1.414(2)
C2 C3 1.387(2)
C2 N1 1.4673(19)
C3 C4 1.379(2)
C3 H3 0.966(19)
C4 C5 1.393(2)
C4 N2 1.459(2)
C5 C6 1.369(2)
C5 H5 0.87(2)
C6 H6 0.953(18)
C7 N3 1.3550(19)
C7 C8 1.375(2)
C7 H7 0.980(18)
C8 C9 1.393(2)
C8 H8 0.88(2)
C9 C10 1.394(2)
C9 C12 1.504(2)
C10 C11 1.375(2)
C10 H10 0.92(2)
C11 N3 1.348(2)
C11 H11 0.91(2)
C12 H12C 0.93(3)
C12 H12B 0.92(4)
C12 H12A 0.98(4)
N1 O3 1.2090(18)
N1 O2 1.2207(19)
N2 O5 1.2274(18)
N2 O4 1.2310(18)
N3 O6 1.3361(15)
O1 H13 0.90(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
O1 C1 C2 C3 178.54(14)
C6 C1 C2 C3 -1.7(2)
O1 C1 C2 N1 -0.9(2)
C6 C1 C2 N1 178.87(14)
C1 C2 C3 C4 0.6(2)
N1 C2 C3 C4 -179.92(14)
C2 C3 C4 C5 0.6(2)
C2 C3 C4 N2 178.96(13)
C3 C4 C5 C6 -0.7(2)
N2 C4 C5 C6 -179.00(14)
C4 C5 C6 C1 -0.5(2)
O1 C1 C6 C5 -178.58(15)
C2 C1 C6 C5 1.6(2)
N3 C7 C8 C9 -0.5(2)
C7 C8 C9 C10 1.2(2)
C7 C8 C9 C12 -179.65(18)
C8 C9 C10 C11 -0.3(2)
C12 C9 C10 C11 -179.48(19)
C9 C10 C11 N3 -1.2(3)
C3 C2 N1 O3 -169.53(15)
C1 C2 N1 O3 9.9(2)
C3 C2 N1 O2 10.4(2)
C1 C2 N1 O2 -170.15(18)
C3 C4 N2 O5 3.1(2)
C5 C4 N2 O5 -178.49(15)
C3 C4 N2 O4 -176.34(14)
C5 C4 N2 O4 2.0(2)
C10 C11 N3 O6 -178.97(15)
C10 C11 N3 C7 1.9(2)
C8 C7 N3 O6 179.83(14)
C8 C7 N3 C11 -1.0(2)
