#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:31:46 +0200 (vie 13 de oct de 2017) $
#$Revision: 201979 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/32/2233246.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_2233246
loop_
_publ_author_name
'Xu, Le-Xing'
'Bai, Xiao-Guang'
'Wang, Ju-Xian'
'Wang, Yu-Cheng'
_publ_section_title
;
 (Z)-Methyl 3-(2,4-dichlorophenyl)-3-hydroxyacrylate
;
_journal_coeditor_code           LR2037
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4
_journal_paper_doi               10.1107/S1600536811051014
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C10 H8 Cl2 O3'
_chemical_formula_moiety         'C10 H8 Cl2 O3'
_chemical_formula_sum            'C10 H8 Cl2 O3'
_chemical_formula_weight         247.06
_chemical_name_systematic
;
(Z)-Methyl 3-(2,4-dichlorophenyl)-3-hydroxyacrylate
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 108.18(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.889(3)
_cell_length_b                   3.8242(8)
_cell_length_c                   18.204(4)
_cell_measurement_reflns_used    5046
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.03
_cell_measurement_theta_min      3.27
_cell_volume                     1050.9(4)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL/PC (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       CCD_Profile_fitting
_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  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5011
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         4.10
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.599
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.184
_refine_ls_abs_structure_details 'Flack (1983), 1177 Friedel pairs'
_refine_ls_abs_structure_Flack   0.07(6)
_refine_ls_extinction_coef       0.0193(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2371
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0343
_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)+(0.0413P)²+0.0839P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0855
_reflns_number_gt                2170
_reflns_number_total             2371
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            lr2037.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2233246
_cod_database_fobs_code          2233246
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'
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
_atom_site_symmetry_multiplicity
C C1 0.58573(13) 0.7958(6) 0.44452(12) 0.0381(5) Uani d . 1 1
C C2 0.53832(13) 0.7161(6) 0.36792(12) 0.0392(5) Uani d . 1 1
C C3 0.57482(16) 0.7526(7) 0.30884(13) 0.0439(5) Uani d . 1 1
H H3 0.5423 0.6944 0.2583 0.053 Uiso calc R 1 1
C C4 0.65998(16) 0.8762(6) 0.32574(14) 0.0478(5) Uani d . 1 1
C C5 0.70941(16) 0.9602(7) 0.40023(15) 0.0520(6) Uani d . 1 1
H H5 0.7669 1.0447 0.4109 0.062 Uiso calc R 1 1
C C6 0.67267(16) 0.9175(7) 0.45842(14) 0.0495(6) Uani d . 1 1
H H6 0.7065 0.9709 0.5088 0.059 Uiso calc R 1 1
C C7 0.55234(15) 0.7569(6) 0.51099(12) 0.0424(5) Uani d . 1 1
C C8 0.47153(15) 0.8564(6) 0.51265(13) 0.0424(5) Uani d . 1 1
H H8 0.4315 0.9548 0.4689 0.051 Uiso calc R 1 1
C C9 0.44659(15) 0.8113(7) 0.58190(13) 0.0441(5) Uani d . 1 1
C C10 0.3367(2) 0.8937(8) 0.64204(16) 0.0612(7) Uani d . 1 1
H H10A 0.3348 0.6501 0.6542 0.092 Uiso calc R 1 1
H H10B 0.2787 0.9934 0.6319 0.092 Uiso calc R 1 1
H H10C 0.3776 1.0126 0.6849 0.092 Uiso calc R 1 1
Cl Cl1 0.43104(3) 0.55059(16) 0.34217(3) 0.05160(19) Uani d . 1 1
Cl Cl2 0.70467(4) 0.9249(2) 0.25046(4) 0.0757(3) Uani d . 1 1
O O1 0.61264(12) 0.6173(6) 0.57216(10) 0.0629(5) Uani d . 1 1
H H1 0.5931 0.6120 0.6088 0.094 Uiso calc R 1 1
O O2 0.49301(12) 0.6776(6) 0.64092(9) 0.0620(5) Uani d . 1 1
O O3 0.36513(11) 0.9310(5) 0.57450(9) 0.0521(4) Uani d . 1 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
C1 0.0333(10) 0.0443(11) 0.0353(10) -0.0018(9) 0.0086(8) -0.0022(8)
C2 0.0305(9) 0.0449(12) 0.0401(11) -0.0029(8) 0.0081(8) -0.0011(9)
C3 0.0384(10) 0.0573(13) 0.0350(12) -0.0029(10) 0.0103(10) -0.0052(10)
C4 0.0450(12) 0.0598(15) 0.0441(12) 0.0013(11) 0.0218(10) 0.0021(11)
C5 0.0355(11) 0.0657(15) 0.0541(14) -0.0083(10) 0.0130(11) -0.0040(12)
C6 0.0368(12) 0.0687(15) 0.0386(12) -0.0056(11) 0.0056(10) -0.0073(10)
C7 0.0412(11) 0.0494(12) 0.0329(11) -0.0003(9) 0.0062(9) -0.0009(9)
C8 0.0390(11) 0.0525(13) 0.0349(11) 0.0029(9) 0.0104(9) 0.0063(10)
C9 0.0423(12) 0.0534(13) 0.0366(11) 0.0007(10) 0.0124(10) 0.0003(10)
C10 0.0577(15) 0.083(2) 0.0505(15) 0.0069(14) 0.0281(13) 0.0036(13)
Cl1 0.0372(3) 0.0734(4) 0.0422(3) -0.0139(3) 0.0093(2) -0.0054(3)
Cl2 0.0592(4) 0.1199(7) 0.0596(4) -0.0099(5) 0.0351(4) 0.0000(5)
O1 0.0466(9) 0.1045(15) 0.0347(9) 0.0182(10) 0.0085(7) 0.0137(9)
O2 0.0507(10) 0.0981(14) 0.0363(9) 0.0163(10) 0.0124(8) 0.0170(9)
O3 0.0434(8) 0.0738(12) 0.0412(9) 0.0096(8) 0.0164(7) 0.0078(8)
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'
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
C2 C1 C6 116.5(2)
C2 C1 C7 125.31(18)
C6 C1 C7 118.17(19)
C3 C2 C1 121.98(19)
C3 C2 Cl1 116.21(16)
C1 C2 Cl1 121.77(16)
C4 C3 C2 119.0(2)
C4 C3 H3 120.5
C2 C3 H3 120.5
C3 C4 C5 121.3(2)
C3 C4 Cl2 118.42(19)
C5 C4 Cl2 120.24(19)
C6 C5 C4 119.0(2)
C6 C5 H5 120.5
C4 C5 H5 120.5
C5 C6 C1 122.2(2)
C5 C6 H6 118.9
C1 C6 H6 118.9
O1 C7 C8 122.4(2)
O1 C7 C1 112.18(19)
C8 C7 C1 125.4(2)
C7 C8 C9 120.5(2)
C7 C8 H8 119.7
C9 C8 H8 119.7
O2 C9 O3 122.4(2)
O2 C9 C8 124.6(2)
O3 C9 C8 113.00(19)
O3 C10 H10A 109.5
O3 C10 H10B 109.5
H10A C10 H10B 109.5
O3 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C7 O1 H1 109.5
C9 O3 C10 115.47(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.396(3)
C1 C6 1.404(3)
C1 C7 1.472(3)
C2 C3 1.379(3)
C2 Cl1 1.740(2)
C3 C4 1.375(3)
C3 H3 0.9300
C4 C5 1.376(4)
C4 Cl2 1.739(2)
C5 C6 1.370(3)
C5 H5 0.9300
C6 H6 0.9300
C7 O1 1.333(3)
C7 C8 1.349(3)
C8 C9 1.445(3)
C8 H8 0.9300
C9 O2 1.210(3)
C9 O3 1.340(3)
C10 O3 1.443(3)
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
O1 H1 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 H1 O2 . 0.82 1.87 2.592(3) 145.6
C3 H3 O2 2_564 0.93 2.48 3.356(3) 156.5
C10 H10B O1 3_455 0.96 2.57 3.492(3) 162.4
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
C6 C1 C2 C3 0.4(4)
C7 C1 C2 C3 -178.6(2)
C6 C1 C2 Cl1 178.08(18)
C7 C1 C2 Cl1 -0.9(3)
C1 C2 C3 C4 -1.0(4)
Cl1 C2 C3 C4 -178.9(2)
C2 C3 C4 C5 0.7(4)
C2 C3 C4 Cl2 -179.34(19)
C3 C4 C5 C6 0.3(4)
Cl2 C4 C5 C6 -179.7(2)
C4 C5 C6 C1 -1.0(4)
C2 C1 C6 C5 0.7(4)
C7 C1 C6 C5 179.7(2)
C2 C1 C7 O1 136.9(2)
C6 C1 C7 O1 -42.0(3)
C2 C1 C7 C8 -44.8(3)
C6 C1 C7 C8 136.3(3)
O1 C7 C8 C9 -0.6(4)
C1 C7 C8 C9 -178.8(2)
C7 C8 C9 O2 -2.1(4)
C7 C8 C9 O3 178.5(2)
O2 C9 O3 C10 0.7(4)
C8 C9 O3 C10 -179.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657352
