#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/86/2208687.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_2208687
loop_
_publ_author_name
'G. Y. S. K. Swamy'
'K. Ravikumar'
'P. Narender'
'V. Jayathirtha Rao'
_publ_section_title
;
 Methyl 3-(2-chloro-5-ethyl-3-pyridyl)-3-hydroxy-2-methylenepropanoate
;
_journal_coeditor_code           OB2007
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1612
_journal_page_last               o1614
_journal_paper_doi               10.1107/S1600536806010646
_journal_volume                  62
_journal_year                    2006
_chemical_formula_moiety         'C12 H14 Cl N O3'
_chemical_formula_sum            'C12 H14 Cl N O3'
_chemical_formula_weight         255.69
_chemical_name_systematic
;
Methyl 3-(2-chloro-5-ethyl-3-pyridinyl)-3-hydroxy-2-
methylenepropanoate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 107.534(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5383(15)
_cell_length_b                   10.9564(16)
_cell_length_c                   11.0465(16)
_cell_measurement_reflns_used    8559
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.93
_cell_measurement_theta_min      2.68
_cell_volume                     1216.2(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
ORTEP3 (Farrugia, 1997) and PLATON (Spek, 2003)
;
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker SMART Apex CCD'
_diffrn_measurement_method       'ω scans'
_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  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0148
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13476
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_min         2.03
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.192
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2858
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0375
_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/[σ²(Fo²)+(0.0659P)²+0.2604P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1097
_reflns_number_gt                2601
_reflns_number_total             2858
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob2007.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2208687
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C C1 0.38886(14) 0.08377(13) 0.38382(13) 0.0438(3) Uani d . 1
H H1 0.3100 0.0491 0.3888 0.053 Uiso calc R 1
C C2 0.43346(12) 0.18944(12) 0.45221(12) 0.0373(3) Uani d . 1
C C3 0.55255(12) 0.23798(11) 0.44385(11) 0.0336(3) Uani d . 1
H H3 0.5864 0.3083 0.4894 0.040 Uiso calc R 1
C C4 0.62226(11) 0.18419(10) 0.36930(10) 0.0306(2) Uani d . 1
C C5 0.56483(12) 0.07867(11) 0.30461(11) 0.0343(3) Uani d . 1
C C6 0.74526(11) 0.24316(11) 0.34959(11) 0.0318(2) Uani d . 1
H H6 0.8034 0.1773 0.3380 0.038 Uiso calc R 1
C C7 0.82380(11) 0.31776(11) 0.46360(11) 0.0345(3) Uani d . 1
C C8 0.90393(12) 0.25279(12) 0.58077(12) 0.0373(3) Uani d . 1
C C9 0.98082(16) 0.06139(16) 0.67093(15) 0.0557(4) Uani d . 1
H H9A 1.0713 0.0896 0.6966 0.084 Uiso calc R 1
H H9B 0.9784 -0.0232 0.6477 0.084 Uiso calc R 1
H H9C 0.9440 0.0710 0.7400 0.084 Uiso calc R 1
C C10 0.82837(15) 0.43869(14) 0.46391(15) 0.0513(4) Uani d . 1
H H10A 0.8801 0.4800 0.5353 0.062 Uiso calc R 1
H H10B 0.7798 0.4822 0.3927 0.062 Uiso calc R 1
C C11 0.36115(14) 0.24967(14) 0.53564(15) 0.0487(3) Uani d . 1
H H11A 0.4067 0.2281 0.6231 0.058 Uiso calc R 1
H H11B 0.3687 0.3374 0.5282 0.058 Uiso calc R 1
C C12 0.21641(18) 0.2187(2) 0.5086(2) 0.0695(5) Uani d . 1
H H12A 0.1699 0.2372 0.4215 0.104 Uiso calc R 1
H H12B 0.1794 0.2657 0.5631 0.104 Uiso calc R 1
H H12C 0.2074 0.1333 0.5237 0.104 Uiso calc R 1
Cl Cl1 0.64013(4) 0.00461(3) 0.20393(3) 0.04954(14) Uani d . 1
N N1 0.45332(11) 0.02826(11) 0.31045(11) 0.0420(3) Uani d . 1
O O1 0.70766(9) 0.31269(9) 0.23601(8) 0.0403(2) Uani d . 1
H H1A 0.6509 0.3627 0.2393 0.061 Uiso calc R 1
O O3 0.96461(12) 0.30231(11) 0.67789(10) 0.0578(3) Uani d . 1
O O4 0.90360(9) 0.13196(9) 0.56315(9) 0.0430(2) 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'
Cl Cl 0.1484 0.1585 '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
N1 C1 C2 123.71(12) ?
N1 C1 H1 118.1 ?
C2 C1 H1 118.1 ?
C1 C2 C3 116.61(12) ?
C1 C2 C11 123.13(12) ?
C3 C2 C11 120.24(11) ?
C4 C3 C2 121.73(11) ?
C4 C3 H3 119.1 ?
C2 C3 H3 119.1 ?
C3 C4 C5 115.42(11) ?
C3 C4 C6 122.01(10) ?
C5 C4 C6 122.31(10) ?
N1 C5 C4 125.24(11) ?
N1 C5 Cl1 114.77(9) ?
C4 C5 Cl1 119.97(9) ?
O1 C6 C7 112.42(10) y
O1 C6 C4 109.37(9) y
C7 C6 C4 112.60(9) ?
O1 C6 H6 107.4 ?
C7 C6 H6 107.4 ?
C4 C6 H6 107.4 ?
C10 C7 C8 117.57(12) ?
C10 C7 C6 123.35(12) ?
C8 C7 C6 119.06(11) ?
O3 C8 O4 123.68(13) ?
O3 C8 C7 124.63(13) ?
O4 C8 C7 111.66(10) ?
O4 C9 H9A 109.5 ?
O4 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
O4 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
C7 C10 H10A 120.0 ?
C7 C10 H10B 120.0 ?
H10A C10 H10B 120.0 ?
C12 C11 C2 116.60(13) ?
C12 C11 H11A 108.1 ?
C2 C11 H11A 108.1 ?
C12 C11 H11B 108.1 ?
C2 C11 H11B 108.1 ?
H11A C11 H11B 107.3 ?
C11 C12 H12A 109.5 ?
C11 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
C11 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
C5 N1 C1 117.28(11) ?
C6 O1 H1A 109.5 ?
C8 O4 C9 115.65(11) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 1.3490(18) y
C1 C2 1.3850(19) ?
C1 H1 0.9300 ?
C2 C3 1.3915(17) ?
C2 C11 1.5129(18) y
C3 C4 1.3891(16) ?
C3 H3 0.9300 ?
C4 C5 1.3975(16) ?
C4 C6 1.5216(16) ?
C5 N1 1.3175(17) y
C5 Cl1 1.7484(12) ?
C6 O1 1.4184(14) y
C6 C7 1.5202(16) ?
C6 H6 0.9800 ?
C7 C10 1.326(2) ?
C7 C8 1.4954(17) ?
C8 O3 1.2004(16) y
C8 O4 1.3380(17) y
C9 O4 1.4470(16) y
C9 H9A 0.9600 ?
C9 H9B 0.9600 ?
C9 H9C 0.9600 ?
C10 H10A 0.9300 ?
C10 H10B 0.9300 ?
C11 C12 1.502(2) ?
C11 H11A 0.9700 ?
C11 H11B 0.9700 ?
C12 H12A 0.9600 ?
C12 H12B 0.9600 ?
C12 H12C 0.9600 ?
O1 H1A 0.8200 ?
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 H1A N1 2_655 0.82 2.11 2.8627(15) 153
C9 H9B O3 2_746 0.96 2.65 3.256(2) 121
C6 H6 Cl1 . 0.98 2.68 3.0942(13) 106
C10 H10B O1 . 0.93 2.50 2.8164(18) 100
C11 H11A Cg1 4_555 0.97 3.08 3.836 136
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
N1 C1 C2 C3 -0.8(2) ?
N1 C1 C2 C11 -179.08(13) ?
C1 C2 C3 C4 0.88(19) ?
C11 C2 C3 C4 179.25(12) ?
C2 C3 C4 C5 -0.28(17) ?
C2 C3 C4 C6 174.02(11) ?
C3 C4 C5 N1 -0.56(18) ?
C6 C4 C5 N1 -174.83(11) ?
C3 C4 C5 Cl1 178.16(9) ?
C6 C4 C5 Cl1 3.88(16) ?
C3 C4 C6 O1 -94.59(13) ?
C5 C4 C6 O1 79.31(13) ?
C3 C4 C6 C7 31.16(15) ?
C5 C4 C6 C7 -154.94(11) ?
O1 C6 C7 C10 15.59(17) ?
C4 C6 C7 C10 -108.49(14) ?
O1 C6 C7 C8 -162.43(10) ?
C4 C6 C7 C8 73.49(13) yes
C10 C7 C8 O3 5.4(2) ?
C6 C7 C8 O3 -176.46(12) ?
C10 C7 C8 O4 -172.55(12) ?
C6 C7 C8 O4 5.58(15) y
C1 C2 C11 C12 -20.9(2) ?
C3 C2 C11 C12 160.84(15) ?
C4 C5 N1 C1 0.7(2) ?
Cl1 C5 N1 C1 -178.07(10) ?
C2 C1 N1 C5 0.0(2) ?
O3 C8 O4 C9 0.90(19) ?
C7 C8 O4 C9 178.88(11) ?
