#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2221884.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_2221884
loop_
_publ_author_name
'Hong, Yan-Ping'
'Song, Bao-An'
'Shangguan, Xin-Chen'
_publ_section_title
;
 Dimethyl
 [(4-fluorophenyl)(6-methoxybenzothiazol-2-ylamino)methyl]phosphonate
;
_journal_coeditor_code           AT2769
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1199
_journal_page_last               o1200
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C17 H18 F N2 O4 P S'
_chemical_formula_moiety         'C17 H18 F N2 O4 P S'
_chemical_formula_sum            'C17 H18 F N2 O4 P S'
_chemical_formula_weight         396.36
_chemical_name_systematic
;
Dimethyl [(4-fluorophenyl)(6-methoxybenzothiazol-2-ylamino)methyl]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'
_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                 122.109(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.761(5)
_cell_length_b                   15.781(4)
_cell_length_c                   14.395(4)
_cell_measurement_reflns_used    5837
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      2.82
_cell_volume                     3802.4(17)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII area-detector'
_diffrn_measurement_method       '\f and \w'
_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  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9669
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         1.94
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  0.9393
_exptl_absorpt_correction_T_min  0.9185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.259
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3428
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0545P)^2^+1.1262P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1149
_reflns_number_gt                2477
_reflns_number_total             3428
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    at2769.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'C 2/c'
_cod_original_cell_volume        3802.4(16)
_cod_database_code               2221884
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_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_refinement_flags
_atom_site_occupancy
S S1 0.07360(4) 0.28313(4) 0.06124(5) 0.0510(2) Uani d . 1
P P1 0.20273(4) 0.09893(4) -0.09266(5) 0.0483(2) Uani d . 1
N N2 0.06939(11) 0.11776(12) 0.06276(16) 0.0477(5) Uani d . 1
C C5 0.10708(13) 0.18124(14) 0.05470(17) 0.0421(5) Uani d . 1
C C4 0.00865(13) 0.14714(14) 0.07713(18) 0.0445(5) Uani d . 1
C C6 0.00177(13) 0.23554(14) 0.07921(17) 0.0438(5) Uani d . 1
C C7 -0.05321(14) 0.27298(16) 0.09682(19) 0.0524(6) Uani d . 1
H H7 -0.0568 0.3317 0.0981 0.063 Uiso calc R 1
C C1 -0.10315(14) 0.22182(16) 0.11256(19) 0.0506(6) Uani d . 1
C C3 -0.04236(14) 0.09767(16) 0.0913(2) 0.0571(7) Uani d . 1
H H3 -0.0395 0.0390 0.0890 0.069 Uiso calc R 1
C C2 -0.09822(15) 0.13484(16) 0.1089(2) 0.0563(6) Uani d . 1
H H2 -0.1326 0.1009 0.1184 0.068 Uiso calc R 1
N N1 0.16956(11) 0.17525(12) 0.04083(17) 0.0524(5) Uani d . 1
H H1 0.1923 0.2209 0.0382 0.063 Uiso calc R 1
C C8 0.19929(13) 0.09419(14) 0.03023(19) 0.0452(6) Uani d . 1
H H8 0.1605 0.0505 0.0196 0.054 Uiso calc R 1
C C9 0.27995(14) 0.06879(14) 0.12740(18) 0.0452(6) Uani d . 1
C C11 0.37489(18) -0.04111(18) 0.2316(2) 0.0659(8) Uani d . 1
H H11 0.3884 -0.0982 0.2439 0.079 Uiso calc R 1
C C10 0.30051(17) -0.01584(16) 0.1484(2) 0.0560(6) Uani d . 1
H H10 0.2630 -0.0567 0.1049 0.067 Uiso calc R 1
C C14 0.33614(15) 0.12855(17) 0.1936(2) 0.0625(7) Uani d . 1
H H14 0.3237 0.1859 0.1810 0.075 Uiso calc R 1
C C12 0.42812(17) 0.0196(2) 0.2955(2) 0.0684(8) Uani d . 1
C C13 0.41102(17) 0.1034(2) 0.2788(3) 0.0751(9) Uani d . 1
H H13 0.4489 0.1435 0.3238 0.090 Uiso calc R 1
F F1 0.50137(11) -0.00510(13) 0.37934(15) 0.1064(7) Uani d . 1
O O1 -0.15552(10) 0.26361(12) 0.13111(15) 0.0658(5) Uani d . 1
C C17 -0.20925(16) 0.21423(19) 0.1466(2) 0.0707(8) Uani d . 1
H H17A -0.2437 0.1822 0.0813 0.106 Uiso calc R 1
H H17B -0.2409 0.2511 0.1617 0.106 Uiso calc R 1
H H17C -0.1794 0.1762 0.2071 0.106 Uiso calc R 1
O O2 0.24876(11) 0.17048(11) -0.09456(13) 0.0612(5) Uani d . 1
O O4 0.23331(10) 0.01050(10) -0.10441(13) 0.0555(4) Uani d . 1
O O3 0.11234(11) 0.09795(13) -0.18384(15) 0.0752(6) Uani d . 1
C C16 0.31296(19) -0.0033(2) -0.0807(3) 0.0886(10) Uani d . 1
H H16A 0.3292 0.0444 -0.1056 0.133 Uiso calc R 1
H H16B 0.3138 -0.0536 -0.1177 0.133 Uiso calc R 1
H H16C 0.3490 -0.0101 -0.0031 0.133 Uiso calc R 1
C C15 0.0861(2) 0.1088(3) -0.2974(3) 0.1293(16) Uani d . 1
H H15A 0.1166 0.1532 -0.3040 0.194 Uiso calc R 1
H H15B 0.0305 0.1236 -0.3386 0.194 Uiso calc R 1
H H15C 0.0938 0.0569 -0.3254 0.194 Uiso calc R 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
S1 0.0591(4) 0.0372(4) 0.0646(4) -0.0040(3) 0.0382(3) 0.0005(3)
P1 0.0512(4) 0.0440(4) 0.0452(3) -0.0112(3) 0.0226(3) -0.0035(3)
N2 0.0461(11) 0.0395(11) 0.0582(12) -0.0059(9) 0.0282(10) -0.0038(9)
C5 0.0426(13) 0.0393(13) 0.0389(12) -0.0061(10) 0.0180(11) -0.0032(9)
C4 0.0451(13) 0.0396(14) 0.0455(13) -0.0073(10) 0.0219(11) -0.0049(10)
C6 0.0455(13) 0.0416(14) 0.0425(12) -0.0052(11) 0.0221(11) -0.0035(10)
C7 0.0572(15) 0.0428(14) 0.0582(15) -0.0044(12) 0.0313(13) -0.0054(11)
C1 0.0490(14) 0.0532(16) 0.0514(14) -0.0053(12) 0.0278(12) -0.0090(11)
C3 0.0579(16) 0.0412(15) 0.0777(18) -0.0081(12) 0.0398(15) -0.0053(12)
C2 0.0549(15) 0.0535(17) 0.0678(16) -0.0135(12) 0.0374(14) -0.0064(12)
N1 0.0529(12) 0.0390(11) 0.0741(14) -0.0097(9) 0.0396(11) -0.0039(10)
C8 0.0488(14) 0.0367(13) 0.0547(14) -0.0089(11) 0.0306(12) -0.0056(10)
C9 0.0538(14) 0.0431(14) 0.0464(13) -0.0045(11) 0.0319(12) -0.0008(10)
C11 0.087(2) 0.0563(18) 0.0570(16) 0.0167(16) 0.0403(17) 0.0113(14)
C10 0.0756(18) 0.0459(16) 0.0494(14) -0.0029(13) 0.0352(14) -0.0002(11)
C14 0.0611(17) 0.0487(16) 0.0647(17) -0.0037(13) 0.0247(15) -0.0009(13)
C12 0.0643(18) 0.079(2) 0.0573(16) 0.0179(16) 0.0290(15) 0.0111(15)
C13 0.0598(18) 0.070(2) 0.0721(19) -0.0062(15) 0.0192(16) -0.0051(15)
F1 0.0756(12) 0.1209(17) 0.0865(13) 0.0313(11) 0.0186(10) 0.0189(11)
O1 0.0625(11) 0.0652(12) 0.0842(13) -0.0062(9) 0.0488(11) -0.0148(10)
C17 0.0617(18) 0.087(2) 0.0781(19) -0.0073(15) 0.0467(16) -0.0076(15)
O2 0.0787(12) 0.0477(10) 0.0626(11) -0.0209(9) 0.0412(10) -0.0049(8)
O4 0.0680(11) 0.0442(10) 0.0622(10) -0.0108(8) 0.0399(9) -0.0105(8)
O3 0.0579(11) 0.0853(14) 0.0560(11) -0.0091(10) 0.0125(10) 0.0023(10)
C16 0.093(2) 0.086(2) 0.125(3) 0.0037(19) 0.084(2) 0.003(2)
C15 0.120(3) 0.149(4) 0.054(2) -0.030(3) 0.003(2) 0.009(2)
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
C6 S1 C5 88.47(10)
O2 P1 O3 116.07(11)
O2 P1 O4 114.04(10)
O3 P1 O4 103.65(10)
O2 P1 C8 113.48(10)
O3 P1 C8 101.64(11)
O4 P1 C8 106.64(10)
C5 N2 C4 109.72(19)
N2 C5 N1 125.0(2)
N2 C5 S1 116.95(17)
N1 C5 S1 118.01(17)
C3 C4 N2 126.0(2)
C3 C4 C6 118.4(2)
N2 C4 C6 115.62(19)
C7 C6 C4 121.8(2)
C7 C6 S1 128.96(18)
C4 C6 S1 109.24(16)
C6 C7 C1 118.8(2)
C6 C7 H7 120.6
C1 C7 H7 120.6
O1 C1 C2 124.3(2)
O1 C1 C7 115.5(2)
C2 C1 C7 120.2(2)
C4 C3 C2 120.3(2)
C4 C3 H3 119.8
C2 C3 H3 119.8
C1 C2 C3 120.5(2)
C1 C2 H2 119.8
C3 C2 H2 119.8
C5 N1 C8 121.96(19)
C5 N1 H1 119.0
C8 N1 H1 119.0
N1 C8 C9 115.05(18)
N1 C8 P1 107.14(15)
C9 C8 P1 110.28(15)
N1 C8 H8 108.0
C9 C8 H8 108.0
P1 C8 H8 108.0
C14 C9 C10 118.3(2)
C14 C9 C8 121.5(2)
C10 C9 C8 120.1(2)
C12 C11 C10 118.1(3)
C12 C11 H11 120.9
C10 C11 H11 120.9
C11 C10 C9 121.7(3)
C11 C10 H10 119.1
C9 C10 H10 119.1
C9 C14 C13 120.3(3)
C9 C14 H14 119.9
C13 C14 H14 119.9
C13 C12 C11 122.6(3)
C13 C12 F1 119.0(3)
C11 C12 F1 118.4(3)
C12 C13 C14 119.0(3)
C12 C13 H13 120.5
C14 C13 H13 120.5
C1 O1 C17 118.1(2)
O1 C17 H17A 109.5
O1 C17 H17B 109.5
H17A C17 H17B 109.5
O1 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C16 O4 P1 123.11(18)
C15 O3 P1 121.1(2)
O4 C16 H16A 109.5
O4 C16 H16B 109.5
H16A C16 H16B 109.5
O4 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
O3 C15 H15A 109.5
O3 C15 H15B 109.5
H15A C15 H15B 109.5
O3 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C6 1.742(2)
S1 C5 1.760(2)
P1 O2 1.4593(17)
P1 O3 1.5560(19)
P1 O4 1.5653(18)
P1 C8 1.807(2)
N2 C5 1.290(3)
N2 C4 1.401(3)
C5 N1 1.355(3)
C4 C3 1.373(3)
C4 C6 1.404(3)
C6 C7 1.374(3)
C7 C1 1.384(3)
C7 H7 0.9300
C1 O1 1.368(3)
C1 C2 1.379(3)
C3 C2 1.388(3)
C3 H3 0.9300
C2 H2 0.9300
N1 C8 1.449(3)
N1 H1 0.8600
C8 C9 1.513(3)
C8 H8 0.9800
C9 C14 1.381(3)
C9 C10 1.382(3)
C11 C12 1.357(4)
C11 C10 1.372(4)
C11 H11 0.9300
C10 H10 0.9300
C14 C13 1.386(4)
C14 H14 0.9300
C12 C13 1.355(4)
C12 F1 1.359(3)
C13 H13 0.9300
O1 C17 1.427(3)
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
O4 C16 1.439(3)
O3 C15 1.438(4)
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
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 O2 7 0.86 1.99 2.793(3) 155.7
C8 H8 N2 1_555 0.98 2.44 2.868(4) 106.02
C14 H14 N1 1_555 0.93 2.62 2.919(5) 99.59
C16 H16C F1 2_655 0.96 2.51 3.2496 133.38
C15 H15B Cg1 2_554 0.96 2.99 3.608(4) 123
C16 H16B Cg3 4_554 0.96 2.96 3.549(4) 121
C17 H17C Cg1 2_555 0.96 2.88 3.625(3) 136