#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/00/2240041.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2240041
loop_
_publ_author_name
'Luo, Kaijun'
'Guo, Qing'
'Wang, Yan'
'Luo, Daibing'
_publ_section_title
;
 Crystal structure of 6-ethoxypyridin-1-ium-2-olate
;
_journal_coeditor_code           ZQ2227
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1146
_journal_paper_doi               10.1107/S1600536814020224
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C7 H9 N O2'
_chemical_formula_moiety         'C7 H9 N O2'
_chemical_formula_sum            'C7 H9 N O2'
_chemical_formula_weight         139.15
_chemical_name_systematic
;
6-Ethoxypyridin-1-ium-2-olate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90
_cell_angle_beta                 93.402(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3037(11)
_cell_length_b                   7.0999(6)
_cell_length_c                   12.0767(15)
_cell_measurement_reflns_used    809
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.2570
_cell_measurement_theta_min      3.7600
_cell_volume                     710.73(14)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution
;
SUPERFLIP (Palatinus & Chapuis, 2007)
;
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Agilent Xcalibur Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2957
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.362
_diffrn_reflns_theta_min         3.064
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2011)
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.327
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         1452
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[σ²(Fo²)+(0.0675P)²+0.0301P]
where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1504
_reflns_number_gt                949
_reflns_number_total             1452
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zq2227sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        710.74(14)
_cod_database_code               2240041
_cod_database_fobs_code          2240041
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
C C1 0.6392(2) 0.3124(3) 0.59009(17) 0.0554(5) Uani d 1
C C2 0.7456(3) 0.1850(3) 0.64769(19) 0.0642(6) Uani d 1
H H2 0.7774 0.2064 0.7218 0.077 Uiso calc 1
C C3 0.8004(3) 0.0333(3) 0.5951(2) 0.0688(7) Uani d 1
H H3 0.8694 -0.0493 0.6344 0.083 Uiso calc 1
C C4 0.7581(3) -0.0052(3) 0.4841(2) 0.0663(7) Uani d 1
H H4 0.7979 -0.1108 0.4492 0.080 Uiso calc 1
C C5 0.6563(2) 0.1176(2) 0.42860(18) 0.0521(5) Uani d 1
C C6 0.6502(3) -0.0472(3) 0.2572(2) 0.0683(7) Uani d 1
H H6A 0.6240 -0.1649 0.2928 0.082 Uiso calc 1
H H6B 0.7658 -0.0431 0.2495 0.082 Uiso calc 1
C C7 0.5627(3) -0.0328(4) 0.1469(2) 0.0824(8) Uani d 1
H H7A 0.5910 -0.1376 0.1017 0.124 Uiso calc 1
H H7B 0.5919 0.0825 0.1117 0.124 Uiso calc 1
H H7C 0.4486 -0.0338 0.1557 0.124 Uiso calc 1
N N1 0.60093(19) 0.2701(2) 0.48106(14) 0.0507(5) Uani d 1
H H1 0.538(3) 0.350(3) 0.445(2) 0.082(8) Uiso d 1
O O1 0.58033(19) 0.4567(2) 0.63138(12) 0.0762(5) Uani d 1
O O2 0.60054(17) 0.11012(17) 0.32261(12) 0.0629(5) Uani d 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0558(12) 0.0567(11) 0.0530(12) -0.0021(9) -0.0032(10) 0.0008(10)
C2 0.0651(14) 0.0644(12) 0.0619(14) 0.0015(10) -0.0066(11) 0.0103(11)
C3 0.0624(14) 0.0641(13) 0.0792(17) 0.0075(11) -0.0027(12) 0.0185(12)
C4 0.0646(14) 0.0521(11) 0.0828(18) 0.0098(10) 0.0096(13) 0.0026(11)
C5 0.0504(11) 0.0462(10) 0.0603(13) -0.0039(8) 0.0081(10) -0.0007(9)
C6 0.0732(15) 0.0593(12) 0.0738(16) 0.0059(10) 0.0173(13) -0.0164(11)
C7 0.0939(19) 0.0759(15) 0.0782(18) 0.0062(13) 0.0121(15) -0.0260(13)
N1 0.0508(10) 0.0472(9) 0.0536(10) 0.0040(7) 0.0000(8) -0.0025(8)
O1 0.0997(13) 0.0716(10) 0.0550(10) 0.0237(9) -0.0148(9) -0.0131(7)
O2 0.0732(10) 0.0531(8) 0.0628(10) 0.0086(6) 0.0059(8) -0.0118(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
N1 C1 C2 115.75(19)
O1 C1 C2 125.0(2)
O1 C1 N1 119.25(17)
C1 C2 H2 120.1
C3 C2 C1 119.9(2)
C3 C2 H2 120.1
C2 C3 H3 118.7
C2 C3 C4 122.6(2)
C4 C3 H3 118.7
C3 C4 H4 121.3
C5 C4 C3 117.5(2)
C5 C4 H4 121.3
N1 C5 C4 120.1(2)
O2 C5 C4 127.98(19)
O2 C5 N1 111.91(17)
H6A C6 H6B 108.5
C7 C6 H6A 110.2
C7 C6 H6B 110.2
O2 C6 H6A 110.2
O2 C6 H6B 110.2
O2 C6 C7 107.33(18)
C6 C7 H7A 109.5
C6 C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7B 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C1 N1 H1 116.0(17)
C5 N1 C1 124.13(18)
C5 N1 H1 119.9(17)
C5 O2 C6 117.46(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.418(3)
C1 N1 1.369(2)
C1 O1 1.251(2)
C2 H2 0.9300
C2 C3 1.344(3)
C3 H3 0.9300
C3 C4 1.392(3)
C4 H4 0.9300
C4 C5 1.363(3)
C5 N1 1.349(2)
C5 O2 1.336(2)
C6 H6A 0.9700
C6 H6B 0.9700
C6 C7 1.483(3)
C6 O2 1.442(2)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
N1 H1 0.87(3)
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
N1 H1 O1 3_666 0.87(2) 1.90(2) 2.762(2) 174(2)
C7 H7A Cg 2_645 0.96 2.90 3.792(3) 155
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
C1 C2 C3 C4 0.5(3)
C2 C1 N1 C5 0.8(3)
C2 C3 C4 C5 -0.3(3)
C3 C4 C5 N1 0.3(3)
C3 C4 C5 O2 179.6(2)
C4 C5 N1 C1 -0.6(3)
C4 C5 O2 C6 1.0(3)
C7 C6 O2 C5 175.32(18)
N1 C1 C2 C3 -0.7(3)
N1 C5 O2 C6 -179.67(16)
O1 C1 C2 C3 179.4(2)
O1 C1 N1 C5 -179.39(18)
O2 C5 N1 C1 -179.95(16)
