#------------------------------------------------------------------------------
#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/51/4035155.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_4035155
loop_
_publ_author_name
'Bisz, Elwira'
'Piontek, Aleksandara'
'Dziuk, Błażej'
'Szostak, Roman'
'Szostak, Michal'
_publ_section_title
;
 Barriers to Rotation in ortho-Substituted Tertiary Aromatic Amides:
 Effect of Chloro-Substitution on Resonance and Distortion.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3159
_journal_page_last               3163
_journal_paper_doi               10.1021/acs.joc.8b00019
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C11 H11 Cl2 N O2'
_chemical_formula_weight         260.11
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 105.323(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4007(7)
_cell_length_b                   21.7382(18)
_cell_length_c                   7.4880(9)
_cell_measurement_reflns_used    7493
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      25.999
_cell_measurement_theta_min      2.972
_cell_volume                     1161.8(2)
_computing_cell_refinement       'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_data_collection       'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector_area_resol_mean '1024 x 1024 with blocks 2 x 2'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  Xcalibur
_diffrn_measurement_method       ω--scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            7493
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.972
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0646P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0899
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2015
_reflns_number_total             2281
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b00019_si_002.cif
_cod_data_source_block           131_2_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035155
_shelx_shelxl_version_number     2014/7
_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
C1 C 0.7073(2) 0.33415(6) 0.43006(19) 0.0144(3) Uani 1 1 d . .
C2 C 0.6598(2) 0.27354(7) 0.37709(19) 0.0159(3) Uani 1 1 d . .
C3 C 0.7926(2) 0.22922(7) 0.3730(2) 0.0194(3) Uani 1 1 d . .
H3 H 0.7571 0.1890 0.3380 0.023 Uiso 1 1 calc R U
C4 C 0.9801(2) 0.24604(7) 0.4223(2) 0.0216(4) Uani 1 1 d . .
H4 H 1.0710 0.2167 0.4207 0.026 Uiso 1 1 calc R U
C5 C 1.0344(2) 0.30601(8) 0.4741(2) 0.0199(3) Uani 1 1 d . .
H5 H 1.1602 0.3171 0.5056 0.024 Uiso 1 1 calc R U
C7 C 0.5618(2) 0.38019(7) 0.45222(19) 0.0147(3) Uani 1 1 d . .
C6 C 0.8970(2) 0.34891(7) 0.4778(2) 0.0164(3) Uani 1 1 d . .
N9 N 0.48565(18) 0.41630(5) 0.30622(17) 0.0156(3) Uani 1 1 d . .
O8 O 0.52096(15) 0.38285(5) 0.60165(14) 0.0194(3) Uani 1 1 d . .
C10 C 0.3426(2) 0.46181(7) 0.3165(2) 0.0174(3) Uani 1 1 d . .
H10A H 0.3914 0.5030 0.3113 0.021 Uiso 1 1 calc R U
H10B H 0.3090 0.4574 0.4325 0.021 Uiso 1 1 calc R U
C11 C 0.1714(2) 0.45206(8) 0.1557(2) 0.0210(3) Uani 1 1 d . .
H11A H 0.1171 0.4121 0.1673 0.025 Uiso 1 1 calc R U
H11B H 0.0785 0.4832 0.1586 0.025 Uiso 1 1 calc R U
O12 O 0.21983(15) 0.45534(5) -0.01664(15) 0.0231(3) Uani 1 1 d . .
C13 C 0.3508(2) 0.40797(7) -0.0273(2) 0.0211(3) Uani 1 1 d . .
H13A H 0.3792 0.4101 -0.1464 0.025 Uiso 1 1 calc R U
H13B H 0.2950 0.3681 -0.0179 0.025 Uiso 1 1 calc R U
C14 C 0.5306(2) 0.41431(7) 0.1260(2) 0.0186(3) Uani 1 1 d . .
H14A H 0.6124 0.3797 0.1227 0.022 Uiso 1 1 calc R U
H14B H 0.5953 0.4517 0.1083 0.022 Uiso 1 1 calc R U
Cl15 Cl 0.42380(5) 0.25373(2) 0.31225(5) 0.02193(14) Uani 1 1 d . .
Cl16 Cl 0.96231(5) 0.42407(2) 0.54676(6) 0.02412(14) Uani 1 1 d . .
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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 '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
C6 C1 C2 116.91(13)
C6 C1 C7 121.27(13)
C2 C1 C7 121.57(13)
C3 C2 C1 122.51(14)
C3 C2 Cl15 119.27(12)
C1 C2 Cl15 118.22(11)
C2 C3 C4 118.51(15)
C2 C3 H3 120.7
C4 C3 H3 120.7
C3 C4 C5 121.13(14)
C3 C4 H4 119.4
C5 C4 H4 119.4
C6 C5 C4 118.54(15)
C6 C5 H5 120.7
C4 C5 H5 120.7
O8 C7 N9 124.03(13)
O8 C7 C1 118.86(13)
N9 C7 C1 117.11(12)
C5 C6 C1 122.39(14)
C5 C6 Cl16 119.30(12)
C1 C6 Cl16 118.31(11)
C7 N9 C10 120.36(12)
C7 N9 C14 125.50(12)
C10 N9 C14 114.13(11)
N9 C10 C11 109.15(12)
N9 C10 H10A 109.9
C11 C10 H10A 109.9
N9 C10 H10B 109.9
C11 C10 H10B 109.9
H10A C10 H10B 108.3
O12 C11 C10 110.74(13)
O12 C11 H11A 109.5
C10 C11 H11A 109.5
O12 C11 H11B 109.5
C10 C11 H11B 109.5
H11A C11 H11B 108.1
C11 O12 C13 110.46(11)
O12 C13 C14 111.38(12)
O12 C13 H13A 109.4
C14 C13 H13A 109.4
O12 C13 H13B 109.4
C14 C13 H13B 109.4
H13A C13 H13B 108.0
N9 C14 C13 109.29(12)
N9 C14 H14A 109.8
C13 C14 H14A 109.8
N9 C14 H14B 109.8
C13 C14 H14B 109.8
H14A C14 H14B 108.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.391(2)
C1 C2 1.394(2)
C1 C7 1.5111(19)
C2 C3 1.383(2)
C2 Cl15 1.7387(15)
C3 C4 1.387(2)
C3 H3 0.9300
C4 C5 1.389(2)
C4 H4 0.9300
C5 C6 1.385(2)
C5 H5 0.9300
C7 O8 1.2350(17)
C7 N9 1.3429(19)
C6 Cl16 1.7429(15)
N9 C10 1.4655(18)
N9 C14 1.4738(18)
C10 C11 1.514(2)
C10 H10A 0.9700
C10 H10B 0.9700
C11 O12 1.4294(19)
C11 H11A 0.9700
C11 H11B 0.9700
O12 C13 1.4305(18)
C13 C14 1.516(2)
C13 H13A 0.9700
C13 H13B 0.9700
C14 H14A 0.9700
C14 H14B 0.9700
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
C3 H3 O8 0.93 2.64 3.4565(19) 146.2 4_565
C10 H10A O8 0.97 2.60 3.5314(18) 160.1 3_666
C11 H11B O12 0.97 2.56 3.4536(19) 153.4 3_565
C13 H13A O8 0.97 2.46 3.3845(18) 158.9 1_554
C14 H14B O12 0.97 2.63 3.5931(19) 171.3 3_665
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
C6 C1 C2 C3 0.7(2)
C7 C1 C2 C3 -173.68(13)
C6 C1 C2 Cl15 -178.82(10)
C7 C1 C2 Cl15 6.84(19)
C1 C2 C3 C4 -0.5(2)
Cl15 C2 C3 C4 178.99(11)
C2 C3 C4 C5 -0.3(2)
C3 C4 C5 C6 0.8(2)
C6 C1 C7 O8 -88.28(17)
C2 C1 C7 O8 85.82(18)
C6 C1 C7 N9 91.20(17)
C2 C1 C7 N9 -94.71(16)
C4 C5 C6 C1 -0.6(2)
C4 C5 C6 Cl16 178.76(12)
C2 C1 C6 C5 -0.1(2)
C7 C1 C6 C5 174.26(13)
C2 C1 C6 Cl16 -179.46(11)
C7 C1 C6 Cl16 -5.10(18)
O8 C7 N9 C10 -1.0(2)
C1 C7 N9 C10 179.59(12)
O8 C7 N9 C14 -179.85(14)
C1 C7 N9 C14 0.7(2)
C7 N9 C10 C11 -126.30(14)
C14 N9 C10 C11 52.71(16)
N9 C10 C11 O12 -56.58(16)
C10 C11 O12 C13 61.69(16)
C11 O12 C13 C14 -60.71(16)
C7 N9 C14 C13 127.39(15)
C10 N9 C14 C13 -51.55(16)
O12 C13 C14 N9 54.31(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 669523
