#------------------------------------------------------------------------------
#$Date: 2022-07-07 00:28:08 +0300 (Thu, 07 Jul 2022) $
#$Revision: 276693 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/26/2022633.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_2022633
loop_
_publ_author_name
'Jones, Roderick C.'
'Twamley, Brendan'
_publ_section_title
;
 Structure of 2-chloro-N-(p-tolyl)propanamide
;
_journal_coden_ASTM              ACSECI
_journal_coeditor_code           DS2252
_journal_issue                   11
_journal_name_full
;
 Acta Crystallographica, Section E: Crystallographic Communications
;
_journal_page_first              1584
_journal_page_last               1588
_journal_paper_doi               10.1107/s2056989018013889
_journal_volume                  74
_journal_year                    2018
_chemical_formula_moiety         'C10 H12 Cl N O'
_chemical_formula_sum            'C10 H12 Cl N O'
_chemical_formula_weight         197.66
_chemical_name_common
;
2-Chloro-N-(p-tolyl)propanamide
;
_chemical_name_systematic
;
2-Chloro-N-(4-methylphenyl)propanamide
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.5119(3)
_cell_length_b                   9.6885(4)
_cell_length_c                   21.8439(8)
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.57
_cell_measurement_theta_min      4.05
_cell_volume                     2013.05(13)
_computing_cell_refinement
;
SAINT (Bruker, 2015)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2015)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker APEXII area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'APEXII CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEXII Kappa Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            18191
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.671
_diffrn_reflns_theta_min         4.047
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.030
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       irregular
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1892
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0382
_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)+(0.0541P)²+1.2115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1819
_reflns_number_total             1892
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ds2252sup1_1a.cif
_cod_data_source_block           1a
_cod_database_code               2022633
_publcif_datablock.id            {1fa5ca5e-c85e-4175-a36b-f68cb60bc8b4}
_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.
;
_shelx_estimated_absorpt_t_max   0.752
_shelx_estimated_absorpt_t_min   0.495
_exptl_absorpt_special_details
;
SADABS (Bruker, 2016a) was used for absorption 
correction. wR2(int) was 0.1002 before and 
0.0601 after correction. The Ratio of minimum 
to maximum transmission is 0.7331. The λ/2 
correction factor is Not present.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C11-C12A = C12-C11
 1.53 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C12A) = Uanis(C12)
4. Others
 Sof(Cl1A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(H12B)=Sof(H12C)=1-FVAR(1)
 Sof(Cl1)=Sof(H11)=Sof(C12)=Sof(H12D)=Sof(H12E)=Sof(H12F)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C11(H11), C11(H11A)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6)
5.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C12A(H12A,H12B,H12C), C12(H12D,H12E,H12F)
;
_iucr_geom_hbonds_special_details
;
Cg1 is the centroid of the C1--C6 ring.
;
_olex2_exptl_crystal_mounting_method 'mounted in oil on a Mitegen holder'
_olex2_submission_original_sample_id RCJ1-2
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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 0.60104(11) 0.01803(8) 0.42660(5) 0.0298(2) Uani 0.783(2) 1 d . . P A 1
Cl1A Cl 0.6006(11) 0.2847(11) 0.3649(4) 0.0328(12) Uani 0.217(2) 1 d . . P A 2
O10 O 0.74965(11) 0.26055(12) 0.48882(5) 0.0281(3) Uani 1 1 d . . . . .
N8 N 0.53542(13) 0.31060(13) 0.52846(6) 0.0208(3) Uani 1 1 d . . . . .
H8 H 0.453(2) 0.2949(17) 0.5247(7) 0.016(4) Uiso 1 1 d . . . . .
C1 C 0.69159(16) 0.46725(17) 0.58476(7) 0.0257(4) Uani 1 1 d . . . . .
H1 H 0.7392 0.4906 0.5480 0.031 Uiso 1 1 calc R . . . .
C2 C 0.73137(17) 0.52711(18) 0.63985(8) 0.0303(4) Uani 1 1 d . . . . .
H2 H 0.8067 0.5915 0.6402 0.036 Uiso 1 1 calc R . . . .
C3 C 0.66349(18) 0.49513(17) 0.69457(8) 0.0286(4) Uani 1 1 d . . . . .
C4 C 0.7043(2) 0.5651(2) 0.75375(9) 0.0408(5) Uani 1 1 d . . . . .
H4A H 0.7236 0.4951 0.7850 0.061 Uiso 1 1 calc GR . . . .
H4B H 0.6272 0.6246 0.7675 0.061 Uiso 1 1 calc GR . . . .
H4C H 0.7888 0.6212 0.7471 0.061 Uiso 1 1 calc GR . . . .
C5 C 0.55361(18) 0.40046(17) 0.69264(7) 0.0286(4) Uani 1 1 d . . . . .
H5 H 0.5058 0.3771 0.7294 0.034 Uiso 1 1 calc R . . . .
C6 C 0.51263(16) 0.33958(16) 0.63802(7) 0.0253(3) Uani 1 1 d . . . . .
H6 H 0.4374 0.2751 0.6376 0.030 Uiso 1 1 calc R . . . .
C7 C 0.58167(15) 0.37290(16) 0.58389(7) 0.0208(3) Uani 1 1 d . . . . .
C9 C 0.62129(15) 0.25772(15) 0.48554(7) 0.0204(3) Uani 1 1 d . . . . .
C11 C 0.54665(16) 0.19425(16) 0.43058(7) 0.0223(3) Uani 1 1 d D . . . .
H11 H 0.4426 0.1988 0.4369 0.027 Uiso 0.783(2) 1 calc R . P A 1
H11A H 0.4428 0.2050 0.4358 0.027 Uiso 0.217(2) 1 calc R . P A 2
C12A C 0.582(2) 0.0409(11) 0.4215(10) 0.035(2) Uani 0.217(2) 1 d D . P A 2
H12A H 0.5437 -0.0127 0.4558 0.053 Uiso 0.217(2) 1 calc GR . P A 2
H12B H 0.6838 0.0290 0.4197 0.053 Uiso 0.217(2) 1 calc GR . P A 2
H12C H 0.5395 0.0084 0.3831 0.053 Uiso 0.217(2) 1 calc GR . P A 2
C12 C 0.5856(12) 0.2688(11) 0.3711(4) 0.035(2) Uani 0.783(2) 1 d D . P A 1
H12D H 0.6871 0.2610 0.3641 0.053 Uiso 0.783(2) 1 calc GR . P A 1
H12E H 0.5597 0.3664 0.3743 0.053 Uiso 0.783(2) 1 calc GR . P A 1
H12F H 0.5350 0.2266 0.3368 0.053 Uiso 0.783(2) 1 calc GR . P A 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C7 N8 H8 118.0(12) . .
C9 N8 H8 116.7(12) . .
C9 N8 C7 124.55(13) . .
C2 C1 H1 120.3 . .
C2 C1 C7 119.47(15) . .
C7 C1 H1 120.3 . .
C1 C2 H2 119.2 . .
C1 C2 C3 121.63(16) . .
C3 C2 H2 119.2 . .
C2 C3 C4 121.00(16) . .
C5 C3 C2 117.95(15) . .
C5 C3 C4 121.02(16) . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4B 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C3 C5 H5 119.4 . .
C6 C5 C3 121.17(15) . .
C6 C5 H5 119.4 . .
C5 C6 H6 120.0 . .
C5 C6 C7 120.01(15) . .
C7 C6 H6 120.0 . .
C1 C7 N8 121.58(14) . .
C1 C7 C6 119.77(14) . .
C6 C7 N8 118.63(14) . .
O10 C9 N8 123.83(14) . .
O10 C9 C11 121.34(13) . .
N8 C9 C11 114.82(13) . .
Cl1 C11 H11 109.6 . .
Cl1A C11 H11A 109.2 . .
C9 C11 Cl1 106.80(10) . .
C9 C11 Cl1A 107.8(4) . .
C9 C11 H11 109.6 . .
C9 C11 H11A 109.2 . .
C9 C11 C12A 113.1(8) . .
C9 C11 C12 111.4(5) . .
C12A C11 Cl1A 108.3(9) . .
C12A C11 H11A 109.2 . .
C12 C11 Cl1 109.8(4) . .
C12 C11 H11 109.6 . .
C11 C12A H12A 109.5 . .
C11 C12A H12B 109.5 . .
C11 C12A H12C 109.5 . .
H12A C12A H12B 109.5 . .
H12A C12A H12C 109.5 . .
H12B C12A H12C 109.5 . .
C11 C12 H12D 109.5 . .
C11 C12 H12E 109.5 . .
C11 C12 H12F 109.5 . .
H12D C12 H12E 109.5 . .
H12D C12 H12F 109.5 . .
H12E C12 H12F 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C11 1.7861(17) .
Cl1A C11 1.758(8) .
O10 C9 1.2233(18) .
N8 H8 0.80(2) .
N8 C7 1.4226(19) .
N8 C9 1.3448(19) .
C1 H1 0.9500 .
C1 C2 1.388(2) .
C1 C7 1.389(2) .
C2 H2 0.9500 .
C2 C3 1.394(2) .
C3 C4 1.511(2) .
C3 C5 1.391(2) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 H5 0.9500 .
C5 C6 1.387(2) .
C6 H6 0.9500 .
C6 C7 1.391(2) .
C9 C11 1.524(2) .
C11 H11 1.0000 .
C11 H11A 1.0000 .
C11 C12A 1.536(9) .
C11 C12 1.532(7) .
C12A H12A 0.9800 .
C12A H12B 0.9800 .
C12A H12C 0.9800 .
C12 H12D 0.9800 .
C12 H12E 0.9800 .
C12 H12F 0.9800 .
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
N8 H8 O10 0.80(2) 2.03(2) 2.8295(16) 174.8(17) 4_456
C11 H11 O10 1.00 2.48 3.3574(18) 146 4_456
C12 H12E Cg1 0.98 2.61 3.503(11) 151 5_666
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
O10 C9 C11 Cl1 59.49(17) . . . .
O10 C9 C11 Cl1A -59.4(4) . . . .
O10 C9 C11 C12A 60.2(10) . . . .
O10 C9 C11 C12 -60.4(5) . . . .
N8 C9 C11 Cl1 -121.40(12) . . . .
N8 C9 C11 Cl1A 119.7(4) . . . .
N8 C9 C11 C12A -120.7(10) . . . .
N8 C9 C11 C12 118.7(5) . . . .
C1 C2 C3 C4 -177.66(16) . . . .
C1 C2 C3 C5 0.1(3) . . . .
C2 C1 C7 N8 178.89(14) . . . .
C2 C1 C7 C6 0.1(2) . . . .
C2 C3 C5 C6 0.0(2) . . . .
C3 C5 C6 C7 0.0(2) . . . .
C4 C3 C5 C6 177.74(16) . . . .
C5 C6 C7 N8 -178.85(14) . . . .
C5 C6 C7 C1 0.0(2) . . . .
C7 N8 C9 O10 -1.9(2) . . . .
C7 N8 C9 C11 179.00(13) . . . .
C7 C1 C2 C3 -0.1(3) . . . .
C9 N8 C7 C1 45.3(2) . . . .
C9 N8 C7 C6 -135.93(15) . . . .

_cod_database_fobs_code 2022633
