#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/40/2014021.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_2014021
loop_
_publ_author_name
'Višnjevac, Aleksandar'
'Tušek-Božić, Ljerka'
_publ_section_title
;
 Two types of monoethyl α-anilinobenzylphosphonates: a zwitterion and
 a molecular compound
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o434
_journal_page_last               o437
_journal_paper_doi               10.1107/S0108270104009497
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C15 H18 N1 O3 P1'
_chemical_formula_moiety         'C15 H18 N1 O3 P1'
_chemical_formula_sum            'C15 H18 N O3 P'
_chemical_formula_weight         291.29
_chemical_name_common            Ethyl-α-anilinobenzylphosphonate
_chemical_name_systematic
;
Monoethyl [α-(phenylaminio)benzyl]phosphonate
;
_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'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 109.940(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.448(2)
_cell_length_b                   6.3510(5)
_cell_length_c                   20.790(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.52
_cell_measurement_theta_min      9.22
_cell_volume                     2910.4(6)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       'non-profiled ω/2θ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54179
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            3121
_diffrn_reflns_theta_full        76.12
_diffrn_reflns_theta_max         76.12
_diffrn_reflns_theta_min         4.01
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.739
_exptl_absorpt_correction_T_max  0.9142
_exptl_absorpt_correction_T_min  0.8623
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.539
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3029
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.091
_refine_ls_R_factor_gt           0.0499
_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)+(0.0680P)²+1.6186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1329
_reflns_number_gt                2177
_reflns_number_total             3029
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hj1006.cif
_cod_data_source_block           I
_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_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C15 H18 N1 O3 P1'
_cod_database_code               2014021
_cod_database_fobs_code          2014021
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_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_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.80232(11) 0.0955(4) 0.41134(13) 0.0113(5) Uani d . 1 . . C
C2 0.80101(12) -0.0697(4) 0.45456(13) 0.0143(5) Uani d . 1 . . C
H2 0.7907 -0.205 0.4375 0.017 Uiso calc R 1 . . H
C3 0.81539(12) -0.0284(5) 0.52370(13) 0.0163(6) Uani d . 1 . . C
H3 0.8147 -0.1374 0.5533 0.02 Uiso calc R 1 . . H
C4 0.83095(12) 0.1742(5) 0.54948(14) 0.0159(6) Uani d . 1 . . C
H4 0.8408 0.2001 0.596 0.019 Uiso calc R 1 . . H
C5 0.83169(13) 0.3364(4) 0.50545(13) 0.0166(6) Uani d . 1 . . C
H5 0.8423 0.4715 0.5225 0.02 Uiso calc R 1 . . H
C6 0.81662(12) 0.2985(4) 0.43564(13) 0.0146(6) Uani d . 1 . . C
H6 0.8162 0.4081 0.4058 0.018 Uiso calc R 1 . . H
C8 0.83959(12) 0.0909(4) 0.31230(13) 0.0133(5) Uani d . 1 . . C
C9 0.89479(12) -0.0350(4) 0.35280(13) 0.0139(5) Uani d . 1 . . C
C10 0.95158(13) 0.0569(5) 0.37410(17) 0.0255(7) Uani d . 1 . . C
H10 0.9555 0.1967 0.363 0.031 Uiso calc R 1 . . H
C11 1.00277(14) -0.0545(6) 0.4116(2) 0.0349(8) Uani d . 1 . . C
H11 1.0407 0.0097 0.4248 0.042 Uiso calc R 1 . . H
C12 0.99742(15) -0.2620(6) 0.42930(17) 0.0291(7) Uani d . 1 . . C
H12 1.0316 -0.3369 0.4553 0.035 Uiso calc R 1 . . H
C13 0.94138(14) -0.3563(5) 0.40831(16) 0.0240(7) Uani d . 1 . . C
H13 0.9376 -0.4953 0.4203 0.029 Uiso calc R 1 . . H
C14 0.89038(13) -0.2453(4) 0.36927(14) 0.0182(6) Uani d . 1 . . C
H14 0.8528 -0.3121 0.3539 0.022 Uiso calc R 1 . . H
C18 0.87425(16) 0.3529(5) 0.19192(17) 0.0258(7) Uani d . 1 . . C
H18A 0.8814 0.4218 0.2356 0.031 Uiso calc R 1 . . H
H18B 0.8375 0.4105 0.1591 0.031 Uiso calc R 1 . . H
C19 0.92712(15) 0.3885(6) 0.16784(18) 0.0322(8) Uani d . 1 . . C
H19A 0.962 0.3148 0.1973 0.048 Uiso calc R 1 . . H
H19B 0.9359 0.5364 0.1689 0.048 Uiso calc R 1 . . H
H19C 0.9172 0.337 0.1219 0.048 Uiso calc R 1 . . H
N7 0.78693(10) 0.0566(4) 0.33775(11) 0.0112(4) Uani d . 1 . . N
O15 0.75680(9) 0.1622(3) 0.18785(9) 0.0155(4) Uani d . 1 . . O
O16 0.81073(8) -0.1950(3) 0.20775(9) 0.0133(4) Uani d . 1 . . O
O17 0.86789(9) 0.1264(3) 0.19876(9) 0.0165(4) Uani d . 1 . . O
P1 0.81344(3) 0.03661(10) 0.21966(3) 0.01098(18) Uani d . 1 . . P
H8 0.8495(15) 0.236(6) 0.3180(17) 0.024(9) Uiso d . 1 . . H
H7A 0.7525(17) 0.149(6) 0.3118(19) 0.038(11) Uiso d . 1 . . H
H7B 0.7712(16) -0.071(6) 0.3273(18) 0.031(10) 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
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-2 0 6
2 -2 -3
6 0 -2
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
C6 C1 C2 121.6(2) ?
C6 C1 N7 118.7(2) ?
C2 C1 N7 119.7(2) ?
C3 C2 C1 118.5(3) ?
C3 C2 H2 120.7 ?
C1 C2 H2 120.7 ?
C2 C3 C4 120.8(3) ?
C2 C3 H3 119.6 ?
C4 C3 H3 119.6 ?
C5 C4 C3 119.6(2) ?
C5 C4 H4 120.2 ?
C3 C4 H4 120.2 ?
C4 C5 C6 120.4(3) ?
C4 C5 H5 119.8 ?
C6 C5 H5 119.8 ?
C1 C6 C5 119.0(2) ?
C1 C6 H6 120.5 ?
C5 C6 H6 120.5 ?
C9 C8 N7 112.0(2) ?
C9 C8 P1 113.58(18) ?
N7 C8 P1 108.50(17) ?
C9 C8 H8 109(2) ?
N7 C8 H8 107(2) ?
P1 C8 H8 107(2) ?
C10 C9 C14 118.1(3) ?
C10 C9 C8 120.3(3) ?
C14 C9 C8 121.6(2) ?
C9 C10 C11 121.4(3) ?
C9 C10 H10 119.3 ?
C11 C10 H10 119.3 ?
C10 C11 C12 119.8(3) ?
C10 C11 H11 120.1 ?
C12 C11 H11 120.1 ?
C13 C12 C11 119.6(3) ?
C13 C12 H12 120.2 ?
C11 C12 H12 120.2 ?
C12 C13 C14 120.3(3) ?
C12 C13 H13 119.8 ?
C14 C13 H13 119.8 ?
C13 C14 C9 120.7(3) ?
C13 C14 H14 119.7 ?
C9 C14 H14 119.7 ?
O17 C18 C19 107.7(3) ?
O17 C18 H18A 110.2 ?
C19 C18 H18A 110.2 ?
O17 C18 H18B 110.2 ?
C19 C18 H18B 110.2 ?
H18A C18 H18B 108.5 ?
C18 C19 H19A 109.5 ?
C18 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C18 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
C1 N7 C8 113.6(2) ?
C1 N7 H7A 109(2) ?
C8 N7 H7A 109(2) ?
C1 N7 H7B 110(2) ?
C8 N7 H7B 111(2) ?
H7A N7 H7B 102(3) ?
C18 O17 P1 119.97(19) ?
O16 P1 O15 118.16(11) y
O16 P1 O17 107.58(11) y
O15 P1 O17 111.28(11) y
O16 P1 C8 109.78(12) y
O15 P1 C8 106.92(12) y
O17 P1 C8 101.92(11) y
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
C1 C6 . 1.384(4) ?
C1 C2 . 1.388(4) ?
C1 N7 . 1.468(3) y
C2 C3 . 1.385(4) ?
C2 H2 . 0.93 ?
C3 C4 . 1.394(4) ?
C3 H3 . 0.93 ?
C4 C5 . 1.382(4) ?
C4 H4 . 0.93 ?
C5 C6 . 1.392(4) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C8 C9 . 1.510(4) y
C8 N7 . 1.516(3) y
C8 P1 . 1.844(3) y
C8 H8 . 0.95(4) ?
C9 C10 . 1.381(4) ?
C9 C14 . 1.391(4) ?
C10 C11 . 1.382(4) ?
C10 H10 . 0.93 ?
C11 C12 . 1.386(5) ?
C11 H11 . 0.93 ?
C12 C13 . 1.373(5) ?
C12 H12 . 0.93 ?
C13 C14 . 1.387(4) ?
C13 H13 . 0.93 ?
C14 H14 . 0.93 ?
C18 O17 . 1.458(3) ?
C18 C19 . 1.504(5) ?
C18 H18A . 0.97 ?
C18 H18B . 0.97 ?
C19 H19A . 0.96 ?
C19 H19B . 0.96 ?
C19 H19C . 0.96 ?
N7 H7A . 0.99(4) ?
N7 H7B . 0.88(4) ?
O15 P1 . 1.4959(19) y
O16 P1 . 1.4895(19) y
O17 P1 . 1.588(2) y
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
N7 H7A O16 4_655 0.99(4) 1.71(4) 2.674(3) 161(3)
N7 H7B O15 4_645 0.88(4) 1.81(4) 2.690(3) 175(4)
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
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.0(4) ?
N7 C1 C2 C3 -179.6(2) ?
C1 C2 C3 C4 -0.1(4) ?
C2 C3 C4 C5 0.4(4) ?
C3 C4 C5 C6 0.4(4) ?
C2 C1 C6 C5 1.8(4) ?
N7 C1 C6 C5 -179.5(2) ?
C4 C5 C6 C1 -1.5(4) ?
N7 C8 C9 C10 -135.5(3) y
P1 C8 C9 C10 101.1(3) y
N7 C8 C9 C14 45.1(3) y
P1 C8 C9 C14 -78.3(3) y
C14 C9 C10 C11 -0.9(5) ?
C8 C9 C10 C11 179.6(3) ?
C9 C10 C11 C12 -1.0(6) ?
C10 C11 C12 C13 1.2(6) ?
C11 C12 C13 C14 0.3(5) ?
C12 C13 C14 C9 -2.3(5) ?
C10 C9 C14 C13 2.5(4) ?
C8 C9 C14 C13 -178.0(3) ?
C6 C1 N7 C8 66.3(3) ?
C2 C1 N7 C8 -115.0(3) ?
C9 C8 N7 C1 53.9(3) y
P1 C8 N7 C1 -179.93(18) ?
C19 C18 O17 P1 -176.7(2) ?
C18 O17 P1 O16 167.8(2) ?
C18 O17 P1 O15 36.9(2) ?
C18 O17 P1 C8 -76.7(2) ?
C9 C8 P1 O16 47.2(2) ?
N7 C8 P1 O16 -78.03(19) ?
C9 C8 P1 O15 176.53(19) ?
N7 C8 P1 O15 51.3(2) ?
C9 C8 P1 O17 -66.6(2) ?
N7 C8 P1 O17 168.15(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10235849
