#------------------------------------------------------------------------------
#$Date: 2015-11-15 04:23:37 +0200 (Sun, 15 Nov 2015) $
#$Revision: 170324 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/13/2241312.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_2241312
loop_
_publ_author_name
'Mariyatra, Mahimaidoss Baby'
'Stoeckli-Evans, Helen'
_publ_section_title
;
 Crystal structure of N-(2,2,2-trichloro-1-hydroxyethyl)formamide
;
_journal_coeditor_code           HG5462
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1501
_journal_page_last               1504
_journal_paper_doi               10.1107/S2056989015020459
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C3 H4 Cl3 N O2'
_chemical_formula_moiety         'C3 H4 Cl3 N O2'
_chemical_formula_sum            'C3 H4 Cl3 N O2'
_chemical_formula_weight         192.42
_chemical_name_systematic
;
N-(2,2,2-Trichloro-1-hydroxyethyl)formamide
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 114.413(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.7964(8)
_cell_length_b                   9.0798(7)
_cell_length_c                   12.2453(7)
_cell_measurement_reflns_used    22309
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.23
_cell_measurement_theta_min      1.62
_cell_volume                     1396.80(16)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2009)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2009)
;
_computing_data_reduction
;
X-RED32 (Stoe & Cie, 2009)
;
_computing_molecular_graphics
;
PLATON  (Spek, 2009) and Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS2014 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'φ + ω scans'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16347
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.705
_diffrn_reflns_theta_min         1.621
_exptl_absorpt_coefficient_mu    1.235
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(MULABS in PLATON; Spek, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.830
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.816
_refine_diff_density_min         -0.548
_refine_ls_extinction_coef       0.0089(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2645
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0304
_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)+(0.0333P)²+1.2964P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0779
_reflns_number_gt                2468
_reflns_number_total             2645
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg5462sup1.cif
_cod_data_source_block           I
_cod_database_code               2241312
_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.
;
_shelxl_version_number           2014/6
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_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_occupancy
Cl Cl1 0.13449(5) 0.04880(6) 0.08600(5) 0.03428(17) Uani d 1
Cl Cl2 0.22308(4) 0.28605(6) -0.00018(5) 0.03123(16) Uani d 1
Cl Cl3 0.28102(5) 0.25302(8) 0.25345(5) 0.04298(19) Uani d 1
O O1 -0.00275(12) 0.31695(18) -0.01499(14) 0.0284(4) Uani d 1
H H1O 0.005(3) 0.366(4) -0.069(3) 0.058(10) Uiso d 1
O O2 0.00144(13) 0.53996(16) 0.21058(14) 0.0295(4) Uani d 1
N N1 0.04737(14) 0.30393(19) 0.18967(16) 0.0213(4) Uani d 1
H H1N 0.0392(18) 0.215(3) 0.207(2) 0.020(6) Uiso d 1
C C1 0.17653(17) 0.2341(2) 0.10963(19) 0.0234(4) Uani d 1
C C2 0.08245(16) 0.3364(2) 0.09670(18) 0.0217(4) Uani d 1
H H2 0.1107(18) 0.434(3) 0.1068(19) 0.020(6) Uiso d 1
C C3 0.00885(17) 0.4079(2) 0.23751(18) 0.0237(4) Uani d 1
H H3 -0.0156(18) 0.374(3) 0.299(2) 0.026(6) Uiso d 1
Cl Cl4 0.64204(5) 0.45558(5) 0.52480(5) 0.03177(16) Uani d 1
Cl Cl5 0.78172(4) 0.22393(6) 0.51229(5) 0.02994(15) Uani d 1
Cl Cl6 0.71719(4) 0.23240(7) 0.70803(5) 0.03280(16) Uani d 1
O O3 0.49315(12) 0.20023(18) 0.51142(15) 0.0274(3) Uani d 1
H H3O 0.497(2) 0.153(3) 0.564(3) 0.036(8) Uiso d 1
O O4 0.50422(13) -0.04575(15) 0.29695(13) 0.0281(3) Uani d 1
N N2 0.54593(14) 0.19299(19) 0.35510(15) 0.0208(4) Uani d 1
H H2N 0.5415(19) 0.274(3) 0.332(2) 0.023(6) Uiso d 1
C C4 0.67565(16) 0.2671(2) 0.55274(18) 0.0216(4) Uani d 1
C C5 0.57819(16) 0.1686(2) 0.48142(18) 0.0206(4) Uani d 1
H H5 0.6025(16) 0.066(2) 0.5015(18) 0.012(5) Uiso d 1
C C6 0.51071(16) 0.0854(2) 0.27421(18) 0.0230(4) Uani d 1
H H6 0.4911(19) 0.119(3) 0.190(2) 0.028(6) Uiso 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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 O1 H1O 112(2)
C3 N1 C2 121.88(17)
C3 N1 H1N 116.3(16)
C2 N1 H1N 120.8(16)
C2 C1 Cl3 110.37(14)
C2 C1 Cl1 110.49(14)
Cl3 C1 Cl1 109.52(11)
C2 C1 Cl2 108.24(14)
Cl3 C1 Cl2 109.15(11)
Cl1 C1 Cl2 109.04(11)
O1 C2 N1 109.04(17)
O1 C2 C1 110.74(16)
N1 C2 C1 109.73(16)
O1 C2 H2 112.1(13)
N1 C2 H2 109.8(14)
C1 C2 H2 105.3(14)
O2 C3 N1 125.03(19)
O2 C3 H3 119.1(14)
N1 C3 H3 115.9(14)
C5 O3 H3O 110(2)
C6 N2 C5 122.84(17)
C6 N2 H2N 118.0(18)
C5 N2 H2N 118.7(18)
C5 C4 Cl4 110.64(14)
C5 C4 Cl5 109.84(14)
Cl4 C4 Cl5 109.91(11)
C5 C4 Cl6 108.82(14)
Cl4 C4 Cl6 108.79(11)
Cl5 C4 Cl6 108.80(11)
O3 C5 N2 109.32(16)
O3 C5 C4 111.15(16)
N2 C5 C4 109.14(16)
O3 C5 H5 111.4(12)
N2 C5 H5 109.6(12)
C4 C5 H5 106.2(12)
O4 C6 N2 125.30(19)
O4 C6 H6 120.9(14)
N2 C6 H6 113.7(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.764(2)
Cl2 C1 1.777(2)
Cl3 C1 1.764(2)
O1 C2 1.398(3)
O1 H1O 0.84(3)
O2 C3 1.236(3)
N1 C3 1.332(3)
N1 C2 1.440(3)
N1 H1N 0.85(2)
C1 C2 1.550(3)
C2 H2 0.96(2)
C3 H3 0.99(2)
Cl4 C4 1.769(2)
Cl5 C4 1.772(2)
Cl6 C4 1.773(2)
O3 C5 1.396(3)
O3 H3O 0.76(3)
O4 C6 1.235(3)
N2 C6 1.332(3)
N2 C5 1.439(3)
N2 H2N 0.78(3)
C4 C5 1.549(3)
C5 H5 0.99(2)
C6 H6 1.00(2)
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 H1O O2 3_565 0.84(3) 1.90(4) 2.731(2) 169(3)
N1 H1N O2 2_545 0.85(2) 2.08(3) 2.893(2) 159(2)
O3 H3O O4 3_656 0.76(3) 1.97(3) 2.721(2) 174(3)
N2 H2N O4 2_655 0.78(3) 2.17(3) 2.917(2) 158(2)
C6 H6 Cl4 2_645 1.00(2) 2.91(2) 3.586(2) 125(2)
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
C3 N1 C2 O1 -91.5(2)
C3 N1 C2 C1 147.08(19)
Cl3 C1 C2 O1 -177.16(14)
Cl1 C1 C2 O1 -55.9(2)
Cl2 C1 C2 O1 63.45(19)
Cl3 C1 C2 N1 -56.7(2)
Cl1 C1 C2 N1 64.54(19)
Cl2 C1 C2 N1 -176.13(14)
C2 N1 C3 O2 -1.8(3)
C6 N2 C5 O3 -95.7(2)
C6 N2 C5 C4 142.52(19)
Cl4 C4 C5 O3 -58.44(19)
Cl5 C4 C5 O3 -179.96(13)
Cl6 C4 C5 O3 61.03(19)
Cl4 C4 C5 N2 62.20(19)
Cl5 C4 C5 N2 -59.31(19)
Cl6 C4 C5 N2 -178.33(14)
C5 N2 C6 O4 -2.1(3)

_cod_database_fobs_code 2241312
