#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/83/2008312.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_2008312
loop_
_publ_author_name
'Bouayad, Abdelouahed'
'Dartiguenave, Michèle'
'Lamandé, Lydia'
'El Ghadraoui, El Houssine'
'Beauchamp, André L.'
_publ_section_title
;
 Nitrate salt of protonated 2-(diethylaminomethyl)phenol
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              681
_journal_page_last               683
_journal_paper_doi               10.1107/S0108270198014218
_journal_volume                  55
_journal_year                    1999
_chemical_formula_iupac          'C11 H18 N O + , N O3 -'
_chemical_formula_moiety         'C11 H18 N2 O4'
_chemical_formula_structural     '(C11 H18 N O) N O3'
_chemical_formula_sum            'C11 H18 N2 O4'
_chemical_formula_weight         242.274
_chemical_name_common
;
2-(Diethylaminomethyl)phenol Nitrate
;
_chemical_name_systematic
;
diethyl(2-hydroxybenzyl)ammonium nitrate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_audit_creation_method           'SHELXL96 (Sheldrick, 1996)'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.0090(13)
_cell_length_b                   15.472(2)
_cell_length_c                   16.216(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    160(3)
_cell_measurement_theta_max      13.6
_cell_measurement_theta_min      11.0
_cell_volume                     2511.2(6)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction
'NRC Crystallographic Computer Programs (Ahmed et al., 1973)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976) in NRCVAX'
_computing_publication_material  'NRCVAX and SHELXL96'
_computing_structure_refinement  SHELXL96
_computing_structure_solution    SHELXS86
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device_type  'Nonius CAD-4'
_diffrn_measurement_method       'θ/2θ scan b/P/b'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_av_sigmaI/netI    0.033
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15341
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.50
_diffrn_standards_decay_%        0.7
_diffrn_standards_interval_time  60
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       prism
_exptl_crystal_F_000             1040.0
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.12
_refine_diff_density_min         -0.13
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.042
_refine_ls_goodness_of_fit_ref   1.209
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_restrained_S_obs      1.209
_refine_ls_R_factor_all          0.060
_refine_ls_R_factor_gt           0.039
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0402P)²+0.3071P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.087
_refine_ls_wR_factor_ref         0.082
_reflns_number_gt                1384
_reflns_number_total             2004
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bk1426.cif
_cod_data_source_block           toul99
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        2511.3(5)
_cod_original_formula_sum        'C11 H18 N O, N O3'
_cod_database_code               2008312
_cod_database_fobs_code          2008312
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, -z'
'-x, y-1/2, -z-1/2'
'x-1/2, y, -z-1/2'
loop_
_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.21686(15) 0.31424(9) 0.37296(10) 0.0380(4) Uani d . 1 . O
H1 0.287(3) 0.2900(16) 0.4015(16) 0.055(8) Uiso d . 1 . H
O10 0.40532(17) 0.23710(10) 0.46247(10) 0.0472(4) Uani d . 1 . O
O11 0.58111(15) 0.15738(10) 0.45795(11) 0.0518(5) Uani d . 1 . O
O12 0.52733(16) 0.23555(12) 0.35186(10) 0.0522(5) Uani d . 1 . O
N1 0.50669(18) 0.21023(11) 0.42319(11) 0.0348(4) Uani d . 1 . N
N7 -0.07463(16) 0.37054(10) 0.38229(10) 0.0251(4) Uani d . 1 . N
H7 -0.0188(19) 0.3464(11) 0.4183(12) 0.018(5) Uiso d . 1 . H
C1 0.2346(2) 0.40096(12) 0.36793(12) 0.0307(5) Uani d . 1 . C
C2 0.1288(2) 0.44883(12) 0.33392(12) 0.0289(5) Uani d . 1 . C
C3 0.1437(2) 0.53704(13) 0.32429(14) 0.0357(5) Uani d . 1 . C
H3 0.066(2) 0.5694(15) 0.3026(15) 0.051(7) Uiso d . 1 . H
C4 0.2609(2) 0.57866(14) 0.34724(15) 0.0406(6) Uani d . 1 . C
H4 0.269(2) 0.6372(16) 0.3390(15) 0.049(7) Uiso d . 1 . H
C5 0.3633(2) 0.53077(14) 0.38152(16) 0.0411(6) Uani d . 1 . C
H5 0.444(3) 0.5563(15) 0.3965(15) 0.047(7) Uiso d . 1 . H
C6 0.3516(2) 0.44229(14) 0.39225(15) 0.0367(5) Uani d . 1 . C
H6 0.423(2) 0.4097(14) 0.4148(14) 0.039(6) Uiso d . 1 . H
C7 0.0048(2) 0.40212(14) 0.30844(13) 0.0322(5) Uani d . 1 . C
H7A 0.026(2) 0.3518(15) 0.2752(14) 0.042(6) Uiso d . 1 . H
H7B -0.055(2) 0.4391(13) 0.2754(14) 0.037(6) Uiso d . 1 . H
C10 -0.1369(2) 0.44391(13) 0.43017(13) 0.0293(5) Uani d . 1 . C
H10A -0.168(2) 0.4218(14) 0.4840(16) 0.043(6) Uiso d . 1 . H
H10B -0.067(2) 0.4854(13) 0.4393(13) 0.034(6) Uiso d . 1 . H
C11 -0.2530(3) 0.48586(18) 0.38728(19) 0.0497(6) Uani d . 1 . C
H11A -0.276(2) 0.5388(17) 0.4181(15) 0.051(7) Uiso d . 1 . H
H11B -0.331(3) 0.4411(18) 0.3796(18) 0.072(9) Uiso d . 1 . H
H11C -0.223(3) 0.5085(17) 0.3334(19) 0.068(9) Uiso d . 1 . H
C12 -0.1755(2) 0.30302(14) 0.35804(16) 0.0349(5) Uani d . 1 . C
H12A -0.221(2) 0.3263(14) 0.3110(15) 0.043(6) Uiso d . 1 . H
H12B -0.238(2) 0.2973(13) 0.4031(14) 0.039(6) Uiso d . 1 . H
C13 -0.1112(3) 0.21656(16) 0.34073(19) 0.0502(7) Uani d . 1 . C
H13A -0.041(3) 0.2195(17) 0.296(2) 0.076(9) Uiso d . 1 . H
H13B -0.184(3) 0.1815(19) 0.3216(19) 0.076(9) Uiso d . 1 . H
H13C -0.057(3) 0.1959(17) 0.388(2) 0.065(8) Uiso d . 1 . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 O1 H1 109.4(16) ?
O12 N1 O11 122.2(2) y
O12 N1 O10 119.9(2) y
O11 N1 O10 117.9(2) y
C12 N7 C10 112.3(2) y
C12 N7 C7 111.6(2) y
C10 N7 C7 112.3(2) y
C12 N7 H7 107.6(12) ?
C10 N7 H7 103.7(12) ?
C7 N7 H7 108.9(12) ?
O1 C1 C6 123.2(2) y
O1 C1 C2 116.5(2) y
C6 C1 C2 120.2(2) y
C3 C2 C1 118.9(2) y
C3 C2 C7 122.4(2) y
C1 C2 C7 118.7(2) y
C2 C3 C4 121.2(2) y
C2 C3 H3 117.0(13) ?
C4 C3 H3 121.7(13) ?
C5 C4 C3 119.1(2) y
C5 C4 H4 121.2(15) ?
C3 C4 H4 119.7(15) ?
C4 C5 C6 121.2(2) y
C4 C5 H5 121.3(14) ?
C6 C5 H5 117.5(14) ?
C5 C6 C1 119.3(2) y
C5 C6 H6 120.7(13) ?
C1 C6 H6 119.9(13) ?
C2 C7 N7 111.9(2) y
C2 C7 H7A 111.0(13) ?
N7 C7 H7A 107.2(13) ?
C2 C7 H7B 112.0(12) ?
N7 C7 H7B 107.3(12) ?
H7A C7 H7B 107.3(18) ?
C11 C10 N7 114.0(2) y
C11 C10 H10A 108.3(13) ?
N7 C10 H10A 109.0(13) ?
C11 C10 H10B 110.3(12) ?
N7 C10 H10B 106.1(12) ?
H10A C10 H10B 109.0(18) ?
C10 C11 H11A 107.9(14) ?
C10 C11 H11B 110.2(15) ?
H11A C11 H11B 116(2) ?
C10 C11 H11C 109.2(16) ?
H11A C11 H11C 103(2) ?
H11B C11 H11C 111(2) ?
N7 C12 C13 112.1(2) y
N7 C12 H12A 105.4(13) ?
C13 C12 H12A 112.8(13) ?
N7 C12 H12B 107.6(13) ?
C13 C12 H12B 109.6(13) ?
H12A C12 H12B 109.2(19) ?
C12 C13 H13A 112.9(16) ?
C12 C13 H13B 103.9(17) ?
H13A C13 H13B 108(2) ?
C12 C13 H13C 112.2(16) ?
H13A C13 H13C 101(2) ?
H13B C13 H13C 119(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.356(2) y
O1 H1 . 0.92(3) ?
O10 N1 . 1.268(2) y
O11 N1 . 1.242(2) y
O12 N1 . 1.239(2) y
N7 C12 . 1.505(3) y
N7 C10 . 1.510(2) y
N7 C7 . 1.518(3) y
N7 H7 . 0.89(2) ?
C1 C6 . 1.391(3) y
C1 C2 . 1.405(3) y
C2 C3 . 1.382(3) y
C2 C7 . 1.495(3) y
C3 C4 . 1.389(3) y
C3 H3 . 0.99(2) ?
C4 C5 . 1.381(3) y
C4 H4 . 0.92(2) ?
C5 C6 . 1.385(3) y
C5 H5 . 0.93(2) ?
C6 H6 . 0.95(2) ?
C7 H7A . 0.97(2) ?
C7 H7B . 0.99(2) ?
C10 C11 . 1.501(3) y
C10 H10A . 0.99(3) ?
C10 H10B . 0.96(2) ?
C11 H11A . 0.99(3) ?
C11 H11B . 1.05(3) ?
C11 H11C . 0.99(3) ?
C12 C13 . 1.511(3) y
C12 H12A . 0.96(2) ?
C12 H12B . 0.97(2) ?
C13 H13A . 1.01(3) ?
C13 H13B . 0.96(3) ?
C13 H13C . 0.99(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
O1 H1 O10 . 0.93(3) 1.74(3) 2.663(2) 173(2)
N7 H7 O10 6_566 0.89(2) 2.45(2) 3.025(2) 123.0(15)
N7 H7 O11 6_566 0.89(2) 2.24(2) 3.054(2) 151.4(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
O1 C1 C2 C3 -177.45(18)
C6 C1 C2 C3 0.7(3)
O1 C1 C2 C7 1.8(3)
C6 C1 C2 C7 179.94(18)
C1 C2 C3 C4 0.3(3)
C7 C2 C3 C4 -178.91(19)
C2 C3 C4 C5 -1.1(3)
C3 C4 C5 C6 0.9(3)
C4 C5 C6 C1 0.1(3)
O1 C1 C6 C5 177.1(2)
C2 C1 C6 C5 -0.9(3)
C3 C2 C7 N7 -109.7(2)
C1 C2 C7 N7 71.1(2)
C12 N7 C7 C2 -163.63(17)
C10 N7 C7 C2 69.3(2)
C12 N7 C10 C11 -54.3(3)
C7 N7 C10 C11 72.5(2)
C10 N7 C12 C13 -157.9(2)
C7 N7 C12 C13 74.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21136507
