#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/60/2216031.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_2216031
loop_
_publ_author_name
'Di-Fan Xu'
'Xiao-Kou Liu'
'Hong-Wu He'
_publ_section_title
;
 Dimethyl
 [(5-ethoxycarbonyl-4-methyl-1,3-thiazol-2-ylamino)phenylmethyl]phosphonate
;
_journal_coeditor_code           KJ2070
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4392
_journal_page_last               o4392
_journal_paper_doi               10.1107/S1600536807051082
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C16 H21 N2 O5 P S'
_chemical_formula_moiety         'C16 H21 N2 O5 P S'
_chemical_formula_sum            'C16 H21 N2 O5 P S'
_chemical_formula_weight         384.38
_chemical_name_systematic
;
Dimethyl
[(5-ethoxycarbonyl-4-methyl-1,3-thiazol-2-ylamino)phenylmethyl]phosphonate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                98.2490(10)
_cell_angle_beta                 103.2990(10)
_cell_angle_gamma                95.6180(10)
_cell_formula_units_Z            2
_cell_length_a                   8.1821(4)
_cell_length_b                   9.9884(5)
_cell_length_c                   11.9142(6)
_cell_measurement_reflns_used    4630
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      19.22
_cell_measurement_theta_min      2.45
_cell_volume                     929.08(8)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8937
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.9717
_exptl_absorpt_correction_T_min  0.9445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.213
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3610
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0449
_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)+(0.0776P)²+0.2203P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1358
_reflns_number_gt                3081
_reflns_number_total             3610
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kj2070.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2216031
_cod_database_fobs_code          2216031
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C C1 -0.0145(4) 0.9080(3) 1.2151(2) 0.0730(8) Uani d . 1
H H1A -0.0472 0.8278 1.2449 0.110 Uiso calc R 1
H H1B -0.0555 0.9849 1.2524 0.110 Uiso calc R 1
H H1C 0.1069 0.9248 1.2310 0.110 Uiso calc R 1
C C2 -0.4101(3) 0.6895(3) 0.8875(3) 0.0758(8) Uani d . 1
H H2A -0.4252 0.5992 0.8430 0.114 Uiso calc R 1
H H2B -0.4895 0.7421 0.8476 0.114 Uiso calc R 1
H H2C -0.4288 0.6842 0.9635 0.114 Uiso calc R 1
C C3 0.2526(3) 0.7897(2) 1.05538(19) 0.0411(5) Uani d . 1
C C4 0.2955(3) 0.6954(2) 1.1295(2) 0.0550(6) Uani d . 1
H H4 0.2265 0.6122 1.1172 0.066 Uiso calc R 1
C C5 0.4383(4) 0.7241(3) 1.2204(3) 0.0643(7) Uani d . 1
H H5 0.4645 0.6614 1.2702 0.077 Uiso calc R 1
C C6 0.5427(4) 0.8459(3) 1.2378(3) 0.0658(7) Uani d . 1
H H6 0.6408 0.8644 1.2983 0.079 Uiso calc R 1
C C7 0.5023(3) 0.9404(3) 1.1659(2) 0.0634(7) Uani d . 1
H H7 0.5726 1.0229 1.1783 0.076 Uiso calc R 1
C C8 0.3567(3) 0.9126(2) 1.0750(2) 0.0504(6) Uani d . 1
H H8 0.3290 0.9769 1.0271 0.060 Uiso calc R 1
C C9 0.0939(3) 0.7586(2) 0.95480(19) 0.0400(5) Uani d . 1
H H9 0.0913 0.8335 0.9097 0.048 Uiso calc R 1
C C10 0.1302(3) 0.6288(2) 0.77337(18) 0.0388(5) Uani d . 1
C C11 0.1807(3) 0.6978(2) 0.6147(2) 0.0490(5) Uani d . 1
C C12 0.2079(3) 0.5648(2) 0.5898(2) 0.0479(5) Uani d . 1
C C13 0.1884(4) 0.8039(3) 0.5388(3) 0.0727(8) Uani d . 1
H H13A 0.2253 0.7672 0.4712 0.109 Uiso calc R 1
H H13B 0.2669 0.8820 0.5821 0.109 Uiso calc R 1
H H13C 0.0780 0.8306 0.5142 0.109 Uiso calc R 1
C C14 0.2556(3) 0.4942(3) 0.4884(2) 0.0563(6) Uani d . 1
C C15 0.3114(4) 0.2811(4) 0.3995(2) 0.0750(9) Uani d . 1
H H15A 0.4186 0.3233 0.3906 0.090 Uiso calc R 1
H H15B 0.2266 0.2748 0.3265 0.090 Uiso calc R 1
C C16 0.3282(5) 0.1417(4) 0.4301(3) 0.0942(11) Uani d . 1
H H16A 0.4169 0.1487 0.5001 0.141 Uiso calc R 1
H H16B 0.3553 0.0842 0.3671 0.141 Uiso calc R 1
H H16C 0.2232 0.1031 0.4427 0.141 Uiso calc R 1
N N1 0.0889(3) 0.63109(17) 0.87592(16) 0.0444(4) Uani d . 1
H H1 0.0584 0.5550 0.8961 0.053 Uiso calc R 1
N N2 0.1400(2) 0.73480(18) 0.72011(16) 0.0454(4) Uani d . 1
O O1 -0.1179(2) 0.62813(15) 1.06639(15) 0.0521(4) Uani d . 1
O O2 -0.0859(2) 0.88752(15) 1.09062(14) 0.0501(4) Uani d . 1
O O3 -0.2396(2) 0.75427(18) 0.90029(15) 0.0559(4) Uani d . 1
O O4 0.2876(3) 0.5468(2) 0.40968(18) 0.0840(7) Uani d . 1
O O5 0.2613(2) 0.36168(19) 0.49423(15) 0.0622(5) Uani d . 1
P P1 -0.09523(7) 0.74679(5) 1.00991(5) 0.03896(18) Uani d . 1
S S1 0.17583(8) 0.47814(5) 0.70125(5) 0.04578(19) Uani d . 1
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'
S S 0.1246 0.1234 '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'
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
O2 C1 H1A 109.5 ?
O2 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
O2 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
O3 C2 H2A 109.5 ?
O3 C2 H2B 109.5 ?
H2A C2 H2B 109.5 ?
O3 C2 H2C 109.5 ?
H2A C2 H2C 109.5 ?
H2B C2 H2C 109.5 ?
C8 C3 C4 118.8(2) ?
C8 C3 C9 120.25(19) ?
C4 C3 C9 120.9(2) ?
C5 C4 C3 120.7(2) ?
C5 C4 H4 119.6 ?
C3 C4 H4 119.6 ?
C4 C5 C6 119.9(2) ?
C4 C5 H5 120.0 ?
C6 C5 H5 120.0 ?
C5 C6 C7 120.2(3) ?
C5 C6 H6 119.9 ?
C7 C6 H6 119.9 ?
C6 C7 C8 120.0(2) ?
C6 C7 H7 120.0 ?
C8 C7 H7 120.0 ?
C3 C8 C7 120.3(2) ?
C3 C8 H8 119.8 ?
C7 C8 H8 119.8 ?
N1 C9 C3 112.70(17) ?
N1 C9 P1 108.02(14) ?
C3 C9 P1 110.69(14) ?
N1 C9 H9 108.4 ?
C3 C9 H9 108.4 ?
P1 C9 H9 108.4 ?
N2 C10 N1 124.56(19) ?
N2 C10 S1 115.39(16) ?
N1 C10 S1 120.05(15) ?
C12 C11 N2 115.7(2) ?
C12 C11 C13 126.5(2) ?
N2 C11 C13 117.8(2) ?
C11 C12 C14 129.6(2) ?
C11 C12 S1 109.96(17) ?
C14 C12 S1 120.46(19) ?
C11 C13 H13A 109.5 ?
C11 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
C11 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
O4 C14 O5 123.6(2) ?
O4 C14 C12 125.2(3) ?
O5 C14 C12 111.1(2) ?
O5 C15 C16 107.4(3) ?
O5 C15 H15A 110.2 ?
C16 C15 H15A 110.2 ?
O5 C15 H15B 110.2 ?
C16 C15 H15B 110.2 ?
H15A C15 H15B 108.5 ?
C15 C16 H16A 109.5 ?
C15 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
C15 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
C10 N1 C9 122.15(17) ?
C10 N1 H1 118.9 ?
C9 N1 H1 118.9 ?
C10 N2 C11 110.26(18) ?
C1 O2 P1 121.86(17) ?
C2 O3 P1 120.73(17) ?
C14 O5 C15 116.3(2) ?
O1 P1 O3 115.59(10) yes
O1 P1 O2 114.25(9) yes
O3 P1 O2 102.76(9) yes
O1 P1 C9 113.98(9) yes
O3 P1 C9 103.11(10) yes
O2 P1 C9 105.80(10) yes
C12 S1 C10 88.65(10) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O2 1.440(3) ?
C1 H1A 0.9600 ?
C1 H1B 0.9600 ?
C1 H1C 0.9600 ?
C2 O3 1.444(3) ?
C2 H2A 0.9600 ?
C2 H2B 0.9600 ?
C2 H2C 0.9600 ?
C3 C8 1.381(3) ?
C3 C4 1.397(3) ?
C3 C9 1.522(3) ?
C4 C5 1.372(4) ?
C4 H4 0.9300 ?
C5 C6 1.376(4) ?
C5 H5 0.9300 ?
C6 C7 1.378(4) ?
C6 H6 0.9300 ?
C7 C8 1.387(4) ?
C7 H7 0.9300 ?
C8 H8 0.9300 ?
C9 N1 1.462(3) yes
C9 P1 1.815(2) ?
C9 H9 0.9800 ?
C10 N2 1.315(3) yes
C10 N1 1.338(3) yes
C10 S1 1.740(2) yes
C11 C12 1.370(3) ?
C11 N2 1.382(3) ?
C11 C13 1.494(3) ?
C12 C14 1.462(3) ?
C12 S1 1.740(2) ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
C14 O4 1.204(3) ?
C14 O5 1.340(3) ?
C15 O5 1.451(3) ?
C15 C16 1.501(5) ?
C15 H15A 0.9700 ?
C15 H15B 0.9700 ?
C16 H16A 0.9600 ?
C16 H16B 0.9600 ?
C16 H16C 0.9600 ?
N1 H1 0.8600 ?
O1 P1 1.4612(15) ?
O2 P1 1.5697(15) ?
O3 P1 1.5625(17) ?
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 2_567 0.86 2.02 2.791(2) 148.2
C13 H13A O4 . 0.96 2.36 3.077(4) 131.0
C9 H9 N2 . 0.98 2.47 2.886(3) 105.4
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
C8 C3 C4 C5 0.1(4)
C9 C3 C4 C5 -179.7(2)
C3 C4 C5 C6 -1.3(4)
C4 C5 C6 C7 1.5(5)
C5 C6 C7 C8 -0.5(4)
C4 C3 C8 C7 0.9(4)
C9 C3 C8 C7 -179.3(2)
C6 C7 C8 C3 -0.7(4)
C8 C3 C9 N1 124.9(2)
C4 C3 C9 N1 -55.3(3)
C8 C3 C9 P1 -114.0(2)
C4 C3 C9 P1 65.8(2)
N2 C11 C12 C14 -178.7(2)
C13 C11 C12 C14 2.2(4)
N2 C11 C12 S1 1.7(3)
C13 C11 C12 S1 -177.3(2)
C11 C12 C14 O4 3.9(4)
S1 C12 C14 O4 -176.6(2)
C11 C12 C14 O5 -176.8(2)
S1 C12 C14 O5 2.7(3)
N2 C10 N1 C9 -16.7(3)
S1 C10 N1 C9 163.21(16)
C3 C9 N1 C10 -100.6(2)
P1 C9 N1 C10 136.84(19)
N1 C10 N2 C11 -178.3(2)
S1 C10 N2 C11 1.8(2)
C12 C11 N2 C10 -2.3(3)
C13 C11 N2 C10 176.9(2)
O4 C14 O5 C15 0.8(4)
C12 C14 O5 C15 -178.5(2)
C16 C15 O5 C14 173.8(2)
C2 O3 P1 O1 26.7(2)
C2 O3 P1 O2 -98.4(2)
C2 O3 P1 C9 151.7(2)
C1 O2 P1 O1 32.1(2)
C1 O2 P1 O3 158.1(2)
C1 O2 P1 C9 -94.1(2)
N1 C9 P1 O1 55.35(17)
C3 C9 P1 O1 -68.48(16)
N1 C9 P1 O3 -70.74(15)
C3 C9 P1 O3 165.43(14)
N1 C9 P1 O2 -178.29(13)
C3 C9 P1 O2 57.88(15)
C11 C12 S1 C10 -0.55(18)
C14 C12 S1 C10 179.8(2)
N2 C10 S1 C12 -0.75(17)
N1 C10 S1 C12 179.34(19)
