#------------------------------------------------------------------------------
#$Date: 2022-03-30 10:45:51 +0300 (Wed, 30 Mar 2022) $
#$Revision: 274107 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/49/8104944.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8104944
loop_
_publ_author_name
'Hosten, Eric C.'
'Betz, Richard'
_publ_section_title
;
 The crystal structure of 3-chloropropionic acid, C3H5ClO2
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              273
_journal_page_last               275
_journal_paper_doi               10.1515/ncrs-2020-0518
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C3 H5 Cl O2'
_chemical_formula_sum            'C3 H5 Cl O2'
_chemical_formula_weight         108.52
_chemical_name_common            '3-chloropropionic acid'
_chemical_name_systematic        '3-chloropropionic acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     SHELXS
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 94.594(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.2011(4)
_cell_length_b                   7.4362(4)
_cell_length_c                   24.1175(15)
_cell_measurement_reflns_used    5017
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      2.74
_cell_volume                     929.78(10)
_computing_cell_refinement       'SAINT [1]'
_computing_data_collection       'APEX2 [1]'
_computing_data_reduction        'SAINT [1]'
_computing_molecular_graphics    'ORTEP3 [3], Mercury [4]'
_computing_publication_material  'SHELXL-97 [2], PLATON [5]'
_computing_structure_refinement  'SHELXL-97 [2]'
_computing_structure_solution    'SHELXS-97 [2]'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_sigmaI/netI    0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            7885
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         28.352
_diffrn_reflns_theta_min         2.867
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8566
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;                                                              
SADABS [6]                                         
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_description       platelet
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.597
_exptl_crystal_size_mid          0.464
_exptl_crystal_size_min          0.246
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         2269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0206P)²+0.7416P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0795
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1926
_reflns_number_total             2269
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0518_suppl.cif
_cod_data_source_block           g
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8104944
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.74346(8) -0.00203(7) 0.05634(2) 0.03771(13) Uani 1 1 d . . . . .
O11 O 1.0112(2) -0.08791(18) 0.22569(5) 0.0342(3) Uani 1 1 d . . . . .
H11 H 0.914093 -0.072739 0.251507 0.051 Uiso 1 1 calc R U . . .
O12 O 0.7817(2) 0.14062(17) 0.18727(5) 0.0300(3) Uani 1 1 d . . . . .
C11 C 0.9545(3) 0.0306(2) 0.18626(6) 0.0233(3) Uani 1 1 d . . . . .
C12 C 1.1290(3) 0.0165(2) 0.13971(7) 0.0282(3) Uani 1 1 d . . . . .
H12A H 1.157037 -0.112232 0.131684 0.034 Uiso 1 1 calc R U . . .
H12B H 1.298420 0.069505 0.152212 0.034 Uiso 1 1 calc R U . . .
C13 C 1.0273(3) 0.1085(2) 0.08684(7) 0.0296(4) Uani 1 1 d . . . . .
H13A H 1.161931 0.107960 0.060057 0.035 Uiso 1 1 calc R U . . .
H13B H 0.985905 0.235247 0.094967 0.035 Uiso 1 1 calc R U . . .
Cl2 Cl 0.24696(9) 0.58842(7) 0.05642(2) 0.04071(13) Uani 1 1 d . . . . .
O21 O 0.5109(2) 0.67876(18) 0.22677(5) 0.0336(3) Uani 1 1 d . . . . .
H21 H 0.408194 0.667580 0.251715 0.050 Uiso 1 1 calc R U . . .
O22 O 0.2794(2) 0.45188(17) 0.18805(5) 0.0297(3) Uani 1 1 d . . . . .
C21 C 0.4530(3) 0.5612(2) 0.18719(6) 0.0232(3) Uani 1 1 d . . . . .
C22 C 0.6285(3) 0.5747(3) 0.14072(6) 0.0283(3) Uani 1 1 d . . . . .
H22A H 0.654470 0.703369 0.132188 0.034 Uiso 1 1 calc R U . . .
H22B H 0.798596 0.523582 0.153590 0.034 Uiso 1 1 calc R U . . .
C23 C 0.5297(3) 0.4800(3) 0.08820(7) 0.0307(4) Uani 1 1 d . . . . .
H23A H 0.488195 0.353689 0.096891 0.037 Uiso 1 1 calc R U . . .
H23B H 0.665796 0.479118 0.061771 0.037 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C11 O11 H11 109.5 . .
O12 C11 O11 124.06(14) . .
O12 C11 C12 123.58(15) . .
O11 C11 C12 112.35(14) . .
C11 C12 C13 114.14(13) . .
C11 C12 H12A 108.7 . .
C13 C12 H12A 108.7 . .
C11 C12 H12B 108.7 . .
C13 C12 H12B 108.7 . .
H12A C12 H12B 107.6 . .
C12 C13 Cl1 111.15(12) . .
C12 C13 H13A 109.4 . .
Cl1 C13 H13A 109.4 . .
C12 C13 H13B 109.4 . .
Cl1 C13 H13B 109.4 . .
H13A C13 H13B 108.0 . .
C21 O21 H21 109.5 . .
O22 C21 O21 124.09(14) . .
O22 C21 C22 123.57(15) . .
O21 C21 C22 112.34(14) . .
C23 C22 C21 114.18(14) . .
C23 C22 H22A 108.7 . .
C21 C22 H22A 108.7 . .
C23 C22 H22B 108.7 . .
C21 C22 H22B 108.7 . .
H22A C22 H22B 107.6 . .
C22 C23 Cl2 111.26(12) . .
C22 C23 H23A 109.4 . .
Cl2 C23 H23A 109.4 . .
C22 C23 H23B 109.4 . .
Cl2 C23 H23B 109.4 . .
H23A C23 H23B 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C13 1.7950(17) .
O11 C11 1.3128(19) .
O11 H11 0.8400 .
O12 C11 1.2170(19) .
C11 C12 1.503(2) .
C12 C13 1.505(2) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
Cl2 C23 1.7941(18) .
O21 C21 1.3115(19) .
O21 H21 0.8400 .
O22 C21 1.2163(19) .
C21 C22 1.504(2) .
C22 C23 1.503(2) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O11 H11 O22 0.84 1.85 2.6839(16) 175.5 2_645
O21 H21 O12 0.84 1.85 2.6831(16) 172.9 2_655
C12 H12B O12 0.99 2.64 3.615(2) 168.1 1_655
C12 H12A Cl2 0.99 2.93 3.8399(18) 152.7 1_645
C22 H22B O22 0.99 2.63 3.603(2) 169.1 1_655
C22 H22A Cl1 0.99 2.91 3.8209(19) 152.6 1_565
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O12 C11 C12 C13 -17.6(2) . . . .
O11 C11 C12 C13 162.88(15) . . . .
C11 C12 C13 Cl1 -66.78(17) . . . .
O22 C21 C22 C23 16.4(2) . . . .
O21 C21 C22 C23 -164.41(15) . . . .
C21 C22 C23 Cl2 67.51(18) . . . .
