#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/52/2215293.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_2215293
loop_
_publ_author_name
'B. Thimme Gowda'
'Sabine Foro'
'Hartmut Fuess '
_publ_section_title
;
 N-(2,3-Dichlorophenyl)-2,2,2-trimethylacetamide
;
_journal_coeditor_code           WN2185
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3788
_journal_page_last               o3788
_journal_paper_doi               10.1107/S160053680703930X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C11 H13 Cl2 N O'
_chemical_formula_moiety         'C11 H13 Cl2 N O'
_chemical_formula_sum            'C11 H13 Cl2 N O'
_chemical_formula_weight         246.12
_chemical_name_systematic
;
N-(2,3-Dichlorophenyl)-2,2,2-trimethylacetamide
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.70(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.206(3)
_cell_length_b                   11.139(3)
_cell_length_c                   10.075(2)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      19.45
_cell_measurement_theta_min      5.67
_cell_volume                     1226.8(5)
_computing_cell_refinement       'CAD-4-PC Software'
_computing_data_collection       'CAD-4-PC Software (Enraf--Nonius, 1996)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1987)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2957
_diffrn_reflns_theta_full        66.93
_diffrn_reflns_theta_max         66.93
_diffrn_reflns_theta_min         4.04
_diffrn_standards_decay_%        1.0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.550
_exptl_absorpt_correction_T_max  0.4015
_exptl_absorpt_correction_T_min  0.2641
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.495
_refine_ls_extinction_coef       0.0058(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2174
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0607
_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)+(0.1081P)²+0.276P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1628
_refine_ls_wR_factor_ref         0.1764
_reflns_number_gt                1680
_reflns_number_total             2174
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            wn2185.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value '\y scan' was replaced with
the value 'psi-scan' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2215293
_cod_database_fobs_code          2215293
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
Cl Cl14 1.22112(9) 0.32462(14) 0.47441(15) 0.1266(6) Uani d . 1
Cl Cl15 0.99510(9) 0.17412(8) 0.51766(9) 0.0841(4) Uani d . 1
O O6 0.7204(2) 0.2107(2) 0.15772(18) 0.0698(6) Uani d . 1
N N7 0.7557(2) 0.2709(2) 0.3746(2) 0.0570(6) Uani d . 1
H H7N 0.7322 0.2703 0.4503 0.068 Uiso calc R 1
C C1 0.6547(4) 0.0286(4) 0.4031(4) 0.1053(14) Uani d . 1
H H1A 0.5933 -0.0254 0.4209 0.126 Uiso calc R 1
H H1B 0.6931 0.0687 0.4858 0.126 Uiso calc R 1
H H1C 0.7151 -0.0159 0.3691 0.126 Uiso calc R 1
C C2 0.5355(3) 0.0561(3) 0.1681(3) 0.0802(10) Uani d . 1
H H2A 0.5961 0.0112 0.1351 0.096 Uiso calc R 1
H H2B 0.4982 0.1136 0.1007 0.096 Uiso calc R 1
H H2C 0.4741 0.0023 0.1864 0.096 Uiso calc R 1
C C3 0.5000(4) 0.1915(4) 0.3513(5) 0.0960(13) Uani d . 1
H H3A 0.4383 0.1376 0.3686 0.115 Uiso calc R 1
H H3B 0.4630 0.2499 0.2848 0.115 Uiso calc R 1
H H3C 0.5382 0.2315 0.4341 0.115 Uiso calc R 1
C C4 0.5956(2) 0.1210(2) 0.2978(3) 0.0525(6) Uani d . 1
C C5 0.6947(2) 0.2046(2) 0.2697(2) 0.0466(6) Uani d . 1
C C8 0.8579(2) 0.3419(2) 0.3625(2) 0.0537(7) Uani d . 1
C C9 0.8410(3) 0.4482(3) 0.2922(3) 0.0674(8) Uani d . 1
H H9 0.7623 0.4743 0.2531 0.081 Uiso calc R 1
C C10 0.9402(4) 0.5161(3) 0.2796(3) 0.0816(10) Uani d . 1
H H10 0.9282 0.5883 0.2322 0.098 Uiso calc R 1
C C11 1.0561(4) 0.4787(3) 0.3358(4) 0.0854(11) Uani d . 1
H H11 1.1226 0.5252 0.3264 0.102 Uiso calc R 1
C C12 1.0746(3) 0.3726(3) 0.4063(3) 0.0735(9) Uani d . 1
C C13 0.9751(3) 0.3034(3) 0.4223(3) 0.0586(7) Uani d . 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
Cl14 0.0569(5) 0.1743(13) 0.1510(12) -0.0080(6) 0.0279(6) -0.0386(9)
Cl15 0.0899(6) 0.0854(6) 0.0783(6) 0.0121(4) 0.0208(4) 0.0081(4)
O6 0.0851(14) 0.0934(15) 0.0356(9) -0.0323(12) 0.0234(9) -0.0110(9)
N7 0.0609(12) 0.0793(15) 0.0333(10) -0.0228(11) 0.0158(9) -0.0086(9)
C1 0.109(3) 0.097(3) 0.098(3) -0.031(2) 0.000(2) 0.045(2)
C2 0.079(2) 0.094(2) 0.0668(19) -0.0310(18) 0.0145(16) -0.0173(17)
C3 0.078(2) 0.095(3) 0.131(3) -0.0221(19) 0.059(2) -0.034(2)
C4 0.0542(13) 0.0578(15) 0.0476(13) -0.0097(11) 0.0155(11) -0.0023(11)
C5 0.0488(12) 0.0558(14) 0.0361(12) -0.0020(10) 0.0114(9) -0.0021(9)
C8 0.0606(15) 0.0651(16) 0.0375(12) -0.0170(12) 0.0157(11) -0.0112(11)
C9 0.082(2) 0.0704(18) 0.0499(14) -0.0113(15) 0.0140(13) -0.0026(13)
C10 0.117(3) 0.071(2) 0.0636(18) -0.029(2) 0.0357(19) -0.0050(15)
C11 0.095(3) 0.091(3) 0.084(2) -0.046(2) 0.049(2) -0.0300(19)
C12 0.0599(16) 0.096(2) 0.0704(19) -0.0200(16) 0.0268(14) -0.0292(17)
C13 0.0625(16) 0.0688(17) 0.0480(14) -0.0087(12) 0.0201(12) -0.0150(12)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C5 N7 C8 121.2(2)
C5 N7 H7N 119.4
C8 N7 H7N 119.4
C4 C1 H1A 109.5
C4 C1 H1B 109.5
H1A C1 H1B 109.5
C4 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C4 C2 H2A 109.5
C4 C2 H2B 109.5
H2A C2 H2B 109.5
C4 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
C4 C3 H3A 109.5
C4 C3 H3B 109.5
H3A C3 H3B 109.5
C4 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
C2 C4 C3 109.8(3)
C2 C4 C1 108.7(3)
C3 C4 C1 109.6(3)
C2 C4 C5 109.6(2)
C3 C4 C5 110.5(2)
C1 C4 C5 108.7(2)
O6 C5 N7 120.6(2)
O6 C5 C4 122.3(2)
N7 C5 C4 117.0(2)
C9 C8 C13 120.1(3)
C9 C8 N7 120.2(3)
C13 C8 N7 119.7(2)
C8 C9 C10 120.0(3)
C8 C9 H9 120.0
C10 C9 H9 120.0
C11 C10 C9 120.7(4)
C11 C10 H10 119.7
C9 C10 H10 119.7
C10 C11 C12 120.0(3)
C10 C11 H11 120.0
C12 C11 H11 120.0
C11 C12 C13 120.2(3)
C11 C12 Cl14 119.8(3)
C13 C12 Cl14 120.0(3)
C8 C13 C12 119.0(3)
C8 C13 Cl15 119.8(2)
C12 C13 Cl15 121.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl14 C12 1.720(4)
Cl15 C13 1.719(3)
O6 C5 1.226(3)
N7 C5 1.346(3)
N7 C8 1.419(3)
N7 H7N 0.8600
C1 C4 1.522(4)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C4 1.516(4)
C2 H2A 0.9600
C2 H2B 0.9600
C2 H2C 0.9600
C3 C4 1.519(4)
C3 H3A 0.9600
C3 H3B 0.9600
C3 H3C 0.9600
C4 C5 1.523(3)
C8 C9 1.371(4)
C8 C13 1.387(4)
C9 C10 1.374(5)
C9 H9 0.9300
C10 C11 1.362(6)
C10 H10 0.9300
C11 C12 1.371(5)
C11 H11 0.9300
C12 C13 1.393(4)
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
N7 H7N O6 4_566 0.86 2.13 2.972(3) 164.9
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 N7 C5 O6 -5.4(4)
C8 N7 C5 C4 173.3(2)
C2 C4 C5 O6 -2.5(4)
C3 C4 C5 O6 -123.5(3)
C1 C4 C5 O6 116.2(3)
C2 C4 C5 N7 178.8(3)
C3 C4 C5 N7 57.8(4)
C1 C4 C5 N7 -62.5(4)
C5 N7 C8 C9 75.9(4)
C5 N7 C8 C13 -104.3(3)
C13 C8 C9 C10 0.8(4)
N7 C8 C9 C10 -179.4(3)
C8 C9 C10 C11 0.3(5)
C9 C10 C11 C12 -0.3(5)
C10 C11 C12 C13 -0.8(5)
C10 C11 C12 Cl14 178.8(3)
C9 C8 C13 C12 -1.8(4)
N7 C8 C13 C12 178.3(2)
C9 C8 C13 Cl15 176.6(2)
N7 C8 C13 Cl15 -3.3(3)
C11 C12 C13 C8 1.9(4)
Cl14 C12 C13 C8 -177.8(2)
C11 C12 C13 Cl15 -176.5(2)
Cl14 C12 C13 Cl15 3.8(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2104711
2 PubChem 2826604
