#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/16/2221644.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_2221644
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Terao, Hiromitsu'
'Fuess, Hartmut'
_publ_section_title
;
 2-Chloro-N-(3,4-dimethylphenyl)acetamide
;
_journal_coeditor_code           DN2441
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1022
_journal_paper_doi               10.1107/S1600536809013051
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C10 H12 Cl N O'
_chemical_formula_moiety         'C10 H12 Cl N O'
_chemical_formula_sum            'C10 H12 Cl N O'
_chemical_formula_weight         197.66
_chemical_name_systematic
;
2-Chloro-N-(3,4-dimethylphenyl)acetamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.415(8)
_cell_angle_beta                 96.492(9)
_cell_angle_gamma                97.767(9)
_cell_formula_units_Z            4
_cell_length_a                   8.3672(9)
_cell_length_b                   9.8076(9)
_cell_length_c                   12.4090(10)
_cell_measurement_reflns_used    4345
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.80
_cell_volume                     996.26(17)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2007)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2004)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2007)
;
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer
with a Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using ω and φ
;
_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  0.0170
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_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            10754
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.80
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.342
_exptl_absorpt_correction_T_max  0.9357
_exptl_absorpt_correction_T_min  0.8680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.232
_refine_ls_extinction_coef       0.024(4)
_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   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0349
_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)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1265
_reflns_number_gt                2874
_reflns_number_total             3634
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2441.cif
_cod_data_source_block           I
_cod_original_cell_volume        996.26(16)
_cod_database_code               2221644
_cod_database_fobs_code          2221644
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.62739(6) 0.60024(5) 0.62240(4) 0.0701(2) Uani d . 1 . .
O O1 0.83974(16) 0.76355(11) 0.45971(10) 0.0569(3) Uani d . 1 . .
N N1 0.81699(17) 0.54085(13) 0.38380(11) 0.0477(3) Uani d . 1 . .
H H1N 0.8113 0.4570 0.3998 0.057 Uiso calc R 1 . .
C C1 0.81633(19) 0.55916(15) 0.27115(14) 0.0447(4) Uani d . 1 . .
C C2 0.9174(2) 0.66380(16) 0.23435(14) 0.0482(4) Uani d . 1 . .
H H2 0.9875 0.7272 0.2846 0.058 Uiso calc R 1 . .
C C3 0.9155(2) 0.67553(17) 0.12342(14) 0.0490(4) Uani d . 1 . .
C C4 0.8120(2) 0.57967(18) 0.04769(14) 0.0542(4) Uani d . 1 . .
C C5 0.7129(2) 0.47505(18) 0.08636(16) 0.0627(5) Uani d . 1 . .
H H5 0.6434 0.4105 0.0367 0.075 Uiso calc R 1 . .
C C6 0.7148(2) 0.46423(17) 0.19551(16) 0.0575(5) Uani d . 1 . .
H H6 0.6474 0.3926 0.2190 0.069 Uiso calc R 1 . .
C C7 0.82545(19) 0.63949(16) 0.46785(14) 0.0446(4) Uani d . 1 . .
C C8 0.8184(2) 0.58415(19) 0.57750(14) 0.0546(4) Uani d . 1 . .
H H8A 0.9049 0.6356 0.6304 0.066 Uiso calc R 1 . .
H H8B 0.8339 0.4876 0.5710 0.066 Uiso calc R 1 . .
C C9 1.0278(3) 0.7913(2) 0.08682(19) 0.0753(6) Uani d . 1 . .
H H9A 1.0907 0.8458 0.1495 0.090 Uiso calc R 1 . .
H H9B 0.9646 0.8488 0.0466 0.090 Uiso calc R 1 . .
H H9C 1.0995 0.7528 0.0411 0.090 Uiso calc R 1 . .
C C10 0.8062(3) 0.5877(3) -0.07390(16) 0.0781(6) Uani d . 1 . .
H H10A 0.9126 0.5838 -0.0949 0.094 Uiso calc R 1 . .
H H10B 0.7710 0.6731 -0.0913 0.094 Uiso calc R 1 . .
H H10C 0.7314 0.5112 -0.1126 0.094 Uiso calc R 1 . .
Cl Cl2 0.90424(8) 0.14166(5) 0.21372(4) 0.0779(2) Uani d . 1 . .
O O2 0.78329(17) 0.24929(11) 0.41405(11) 0.0628(4) Uani d . 1 . .
N N2 0.74319(15) 0.04521(12) 0.48565(10) 0.0414(3) Uani d . 1 . .
H H2N 0.7539 -0.0406 0.4734 0.050 Uiso calc R 1 . .
C C11 0.67313(18) 0.08227(14) 0.58097(12) 0.0379(3) Uani d . 1 . .
C C12 0.66625(19) -0.01217(15) 0.65716(12) 0.0428(4) Uani d . 1 . .
H H12 0.7076 -0.0946 0.6435 0.051 Uiso calc R 1 . .
C C13 0.5996(2) 0.01258(16) 0.75308(13) 0.0458(4) Uani d . 1 . .
C C14 0.53726(19) 0.13642(16) 0.77369(13) 0.0459(4) Uani d . 1 . .
C C15 0.5432(2) 0.22884(16) 0.69622(14) 0.0503(4) Uani d . 1 . .
H H15 0.5011 0.3110 0.7092 0.060 Uiso calc R 1 . .
C C16 0.60886(19) 0.20418(15) 0.60076(14) 0.0466(4) Uani d . 1 . .
H H16 0.6102 0.2683 0.5501 0.056 Uiso calc R 1 . .
C C17 0.79504(19) 0.12730(15) 0.41182(13) 0.0425(4) Uani d . 1 . .
C C18 0.8760(2) 0.05019(18) 0.32656(13) 0.0519(4) Uani d . 1 . .
H H18A 0.8097 -0.0386 0.3018 0.062 Uiso calc R 1 . .
H H18B 0.9808 0.0326 0.3598 0.062 Uiso calc R 1 . .
C C19 0.5979(3) -0.0922(2) 0.83395(16) 0.0698(6) Uani d . 1 . .
H H19A 0.6609 -0.0513 0.9016 0.084 Uiso calc R 1 . .
H H19B 0.6439 -0.1707 0.8058 0.084 Uiso calc R 1 . .
H H19C 0.4879 -0.1216 0.8462 0.084 Uiso calc R 1 . .
C C20 0.4663(2) 0.1688(2) 0.87824(15) 0.0639(5) Uani d . 1 . .
H H20A 0.5468 0.1673 0.9396 0.077 Uiso calc R 1 . .
H H20B 0.3736 0.1008 0.8819 0.077 Uiso calc R 1 . .
H H20C 0.4333 0.2589 0.8797 0.077 Uiso calc R 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 C1 . . 127.45(13) ?
C7 N1 H1N . . 116.3 ?
C1 N1 H1N . . 116.3 ?
C6 C1 C2 . . 118.88(16) ?
C6 C1 N1 . . 118.09(15) ?
C2 C1 N1 . . 122.98(14) ?
C1 C2 C3 . . 120.99(15) ?
C1 C2 H2 . . 119.5 ?
C3 C2 H2 . . 119.5 ?
C2 C3 C4 . . 119.72(16) ?
C2 C3 C9 . . 119.26(16) ?
C4 C3 C9 . . 121.02(17) ?
C5 C4 C3 . . 118.29(16) ?
C5 C4 C10 . . 120.04(17) ?
C3 C4 C10 . . 121.68(18) ?
C6 C5 C4 . . 121.78(16) ?
C6 C5 H5 . . 119.1 ?
C4 C5 H5 . . 119.1 ?
C5 C6 C1 . . 120.34(17) ?
C5 C6 H6 . . 119.8 ?
C1 C6 H6 . . 119.8 ?
O1 C7 N1 . . 124.51(15) ?
O1 C7 C8 . . 121.48(15) ?
N1 C7 C8 . . 114.00(14) ?
C7 C8 Cl1 . . 109.74(12) ?
C7 C8 H8A . . 109.7 ?
Cl1 C8 H8A . . 109.7 ?
C7 C8 H8B . . 109.7 ?
Cl1 C8 H8B . . 109.7 ?
H8A C8 H8B . . 108.2 ?
C3 C9 H9A . . 109.5 ?
C3 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C3 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C4 C10 H10A . . 109.5 ?
C4 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C4 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C17 N2 C11 . . 128.24(12) ?
C17 N2 H2N . . 115.9 ?
C11 N2 H2N . . 115.9 ?
C12 C11 C16 . . 118.87(14) ?
C12 C11 N2 . . 116.84(13) ?
C16 C11 N2 . . 124.27(13) ?
C11 C12 C13 . . 121.92(14) ?
C11 C12 H12 . . 119.0 ?
C13 C12 H12 . . 119.0 ?
C12 C13 C14 . . 119.13(15) ?
C12 C13 C19 . . 119.77(15) ?
C14 C13 C19 . . 121.09(16) ?
C15 C14 C13 . . 118.25(15) ?
C15 C14 C20 . . 120.87(16) ?
C13 C14 C20 . . 120.88(16) ?
C16 C15 C14 . . 122.68(15) ?
C16 C15 H15 . . 118.7 ?
C14 C15 H15 . . 118.7 ?
C15 C16 C11 . . 119.14(14) ?
C15 C16 H16 . . 120.4 ?
C11 C16 H16 . . 120.4 ?
O2 C17 N2 . . 124.59(15) ?
O2 C17 C18 . . 123.45(14) ?
N2 C17 C18 . . 111.93(13) ?
C17 C18 Cl2 . . 112.79(12) ?
C17 C18 H18A . . 109.0 ?
Cl2 C18 H18A . . 109.0 ?
C17 C18 H18B . . 109.0 ?
Cl2 C18 H18B . . 109.0 ?
H18A C18 H18B . . 107.8 ?
C13 C19 H19A . . 109.5 ?
C13 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C13 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C14 C20 H20A . . 109.5 ?
C14 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C14 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C8 . 1.7731(19) ?
O1 C7 . 1.2213(18) ?
N1 C7 . 1.343(2) ?
N1 C1 . 1.426(2) ?
N1 H1N . 0.8600 ?
C1 C6 . 1.382(2) ?
C1 C2 . 1.385(2) ?
C2 C3 . 1.391(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.395(2) ?
C3 C9 . 1.511(3) ?
C4 C5 . 1.387(3) ?
C4 C10 . 1.514(3) ?
C5 C6 . 1.367(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.516(2) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
Cl2 C18 . 1.7539(16) ?
O2 C17 . 1.2117(18) ?
N2 C17 . 1.3454(19) ?
N2 C11 . 1.4171(19) ?
N2 H2N . 0.8600 ?
C11 C12 . 1.385(2) ?
C11 C16 . 1.388(2) ?
C12 C13 . 1.385(2) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.398(2) ?
C13 C19 . 1.503(2) ?
C14 C15 . 1.383(2) ?
C14 C20 . 1.511(2) ?
C15 C16 . 1.376(2) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C17 C18 . 1.517(2) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
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
N1 H1N O2 . 0.86 2.05 2.8992(16) 171.5
N2 H2N O1 1_545 0.86 2.14 2.9802(16) 166.2
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 C1 C6 . . . . -140.52(16) ?
C7 N1 C1 C2 . . . . 42.3(2) ?
C6 C1 C2 C3 . . . . 1.1(2) ?
N1 C1 C2 C3 . . . . 178.30(14) ?
C1 C2 C3 C4 . . . . -0.8(2) ?
C1 C2 C3 C9 . . . . 180.00(16) ?
C2 C3 C4 C5 . . . . 0.2(2) ?
C9 C3 C4 C5 . . . . 179.41(17) ?
C2 C3 C4 C10 . . . . -179.69(17) ?
C9 C3 C4 C10 . . . . -0.5(3) ?
C3 C4 C5 C6 . . . . 0.0(3) ?
C10 C4 C5 C6 . . . . 179.91(18) ?
C4 C5 C6 C1 . . . . 0.4(3) ?
C2 C1 C6 C5 . . . . -0.9(3) ?
N1 C1 C6 C5 . . . . -178.21(16) ?
C1 N1 C7 O1 . . . . -2.7(3) ?
C1 N1 C7 C8 . . . . 178.29(15) ?
O1 C7 C8 Cl1 . . . . 73.33(19) ?
N1 C7 C8 Cl1 . . . . -107.59(15) ?
C17 N2 C11 C12 . . . . -164.70(14) ?
C17 N2 C11 C16 . . . . 16.8(2) ?
C16 C11 C12 C13 . . . . -1.1(2) ?
N2 C11 C12 C13 . . . . -179.64(14) ?
C11 C12 C13 C14 . . . . 0.1(2) ?
C11 C12 C13 C19 . . . . -178.89(16) ?
C12 C13 C14 C15 . . . . 0.7(2) ?
C19 C13 C14 C15 . . . . 179.67(16) ?
C12 C13 C14 C20 . . . . -178.87(15) ?
C19 C13 C14 C20 . . . . 0.1(3) ?
C13 C14 C15 C16 . . . . -0.5(3) ?
C20 C14 C15 C16 . . . . 179.05(16) ?
C14 C15 C16 C11 . . . . -0.5(3) ?
C12 C11 C16 C15 . . . . 1.2(2) ?
N2 C11 C16 C15 . . . . 179.71(14) ?
C11 N2 C17 O2 . . . . -3.0(3) ?
C11 N2 C17 C18 . . . . 175.03(14) ?
O2 C17 C18 Cl2 . . . . -15.1(2) ?
N2 C17 C18 Cl2 . . . . 166.82(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139076453
