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#$Date: 2025-08-18 18:02:58 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/52/04/1520431.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_1520431
loop_
_publ_author_name
'Coles, Susanne L.'
'Threlfall, Terry L.'
'Hursthouse, Michael B.'
_publ_section_title
;
 N-(3-bromophenyl)acetamide
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              1381
_journal_year                    2009
_chemical_formula_sum            'C8 H8 Br N O'
_chemical_formula_weight         214.06
_chemical_name_systematic
;
N-(3-bromophenyl)acetamide
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 108.655(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.8550(15)
_cell_length_b                   5.0020(5)
_cell_length_c                   18.3360(16)
_cell_measurement_reflns_used    38576
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1725.4(3)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0934
_diffrn_reflns_av_sigmaI/netI    0.0775
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18697
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.67
_exptl_absorpt_coefficient_mu    4.706
_exptl_absorpt_correction_T_max  0.7655
_exptl_absorpt_correction_T_min  0.2313
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.845
_refine_diff_density_min         -0.978
_refine_diff_density_rms         0.144
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3912
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0648
_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)+(0.1057P)²+1.5470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1647
_refine_ls_wR_factor_ref         0.1914
_reflns_number_gt                2647
_reflns_number_total             3912
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-1381.cif
_cod_data_source_block           2008lsh168
_cod_depositor_comments
;
Citation :
Coles (nee Huth), Susanne L. and Threlfall, Terry L. and 
Hursthouse, Michael B. (2009) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/1381)

More at:
http://ecrystals.chem.soton.ac.uk/1381/

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 3392 2015-05-12 13:50:21Z andrius 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1520431
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_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3384(2) 0.9292(9) 0.1928(3) 0.0306(10) Uani 1 1 d . . .
C2 C 0.3654(2) 0.9375(9) 0.2732(3) 0.0335(10) Uani 1 1 d . . .
H2 H 0.3487 1.0660 0.3016 0.040 Uiso 1 1 calc R . .
C3 C 0.4170(3) 0.7526(10) 0.3103(3) 0.0387(12) Uani 1 1 d . . .
C4 C 0.4424(3) 0.5618(10) 0.2719(3) 0.0379(11) Uani 1 1 d . . .
H4 H 0.4771 0.4358 0.2993 0.046 Uiso 1 1 calc R . .
C5 C 0.4162(3) 0.5576(10) 0.1924(3) 0.0390(12) Uani 1 1 d . . .
H5 H 0.4340 0.4305 0.1647 0.047 Uiso 1 1 calc R . .
C6 C 0.3639(3) 0.7386(9) 0.1526(3) 0.0342(11) Uani 1 1 d . . .
H6 H 0.3456 0.7321 0.0980 0.041 Uiso 1 1 calc R . .
C7 C 0.2491(2) 1.2963(9) 0.1725(3) 0.0303(10) Uani 1 1 d . . .
C8 C 0.1919(3) 1.4336(10) 0.1076(3) 0.0381(11) Uani 1 1 d . . .
H8A H 0.1547 1.5015 0.1272 0.057 Uiso 1 1 calc R . .
H8B H 0.1713 1.3051 0.0662 0.057 Uiso 1 1 calc R . .
H8C H 0.2130 1.5827 0.0878 0.057 Uiso 1 1 calc R . .
N1 N 0.2834(2) 1.0960(8) 0.1488(2) 0.0323(9) Uani 1 1 d D . .
O1 O 0.26192(18) 1.3615(7) 0.24031(19) 0.0339(7) Uani 1 1 d . . .
H1N H 0.266(3) 1.064(11) 0.0987(13) 0.045(15) Uiso 1 1 d D . .
C11 C 0.1666(3) 1.7849(10) 0.3421(3) 0.0342(11) Uani 1 1 d . . .
C12 C 0.1274(3) 1.8730(11) 0.3886(3) 0.0352(11) Uani 1 1 d . . .
H12 H 0.1337 1.7946 0.4375 0.042 Uiso 1 1 calc R . .
C13 C 0.0792(3) 2.0772(11) 0.3614(3) 0.0376(11) Uani 1 1 d . . .
C14 C 0.0670(3) 2.1964(11) 0.2905(3) 0.0396(12) Uani 1 1 d . . .
H14 H 0.0335 2.3372 0.2737 0.048 Uiso 1 1 calc R . .
C15 C 0.1053(3) 2.1032(11) 0.2451(3) 0.0425(13) Uani 1 1 d . . .
H15 H 0.0972 2.1783 0.1955 0.051 Uiso 1 1 calc R . .
C16 C 0.1555(3) 1.9016(11) 0.2704(3) 0.0373(11) Uani 1 1 d . . .
H16 H 0.1823 1.8434 0.2387 0.045 Uiso 1 1 calc R . .
C17 C 0.2489(3) 1.4756(10) 0.4349(3) 0.0371(11) Uani 1 1 d . . .
C18 C 0.3021(3) 1.2573(11) 0.4410(3) 0.0414(13) Uani 1 1 d . . .
H18A H 0.3500 1.3257 0.4671 0.062 Uiso 1 1 calc R . .
H18B H 0.2990 1.1954 0.3893 0.062 Uiso 1 1 calc R . .
H18C H 0.2921 1.1081 0.4706 0.062 Uiso 1 1 calc R . .
N11 N 0.2182(2) 1.5802(8) 0.3641(2) 0.0348(9) Uani 1 1 d D . .
O11 O 0.2348(2) 1.5547(8) 0.49230(19) 0.0423(9) Uani 1 1 d . . .
Br1 Br 0.45410(3) 0.76842(13) 0.41984(3) 0.0510(2) Uani 1 1 d . . .
Br11 Br 0.02506(3) 2.19534(16) 0.42483(4) 0.0571(3) Uani 1 1 d . . .
H11N H 0.234(3) 1.511(11) 0.329(3) 0.051(17) Uiso 1 1 d 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'
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'
Br Br -0.2901 2.4595 '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
C6 C1 C2 119.7(5) . .
C6 C1 N1 116.7(4) . .
C2 C1 N1 123.5(4) . .
C3 C2 C1 118.1(5) . .
C3 C2 H2 121.0 . .
C1 C2 H2 121.0 . .
C4 C3 C2 123.1(5) . .
C4 C3 Br1 119.2(4) . .
C2 C3 Br1 117.7(4) . .
C3 C4 C5 118.4(5) . .
C3 C4 H4 120.8 . .
C5 C4 H4 120.8 . .
C4 C5 C6 120.5(5) . .
C4 C5 H5 119.7 . .
C6 C5 H5 119.7 . .
C5 C6 C1 120.1(5) . .
C5 C6 H6 119.9 . .
C1 C6 H6 119.9 . .
O1 C7 N1 123.7(4) . .
O1 C7 C8 122.1(4) . .
N1 C7 C8 114.2(4) . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C7 N1 C1 129.2(4) . .
C7 N1 H1N 113(4) . .
C1 N1 H1N 118(4) . .
C16 C11 C12 119.6(5) . .
C16 C11 N11 117.0(5) . .
C12 C11 N11 123.4(5) . .
C13 C12 C11 118.1(5) . .
C13 C12 H12 120.9 . .
C11 C12 H12 120.9 . .
C14 C13 C12 123.5(5) . .
C14 C13 Br11 118.5(4) . .
C12 C13 Br11 118.0(4) . .
C15 C14 C13 117.4(5) . .
C15 C14 H14 121.3 . .
C13 C14 H14 121.3 . .
C14 C15 C16 121.4(5) . .
C14 C15 H15 119.3 . .
C16 C15 H15 119.3 . .
C15 C16 C11 120.0(5) . .
C15 C16 H16 120.0 . .
C11 C16 H16 120.0 . .
O11 C17 N11 122.5(5) . .
O11 C17 C18 121.1(5) . .
N11 C17 C18 116.4(4) . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C17 N11 C11 128.2(4) . .
C17 N11 H11N 114(4) . .
C11 N11 H11N 118(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.396(7) .
C1 C2 1.399(7) .
C1 N1 1.406(6) .
C2 C3 1.387(7) .
C2 H2 0.9500 .
C3 C4 1.374(8) .
C3 Br1 1.907(5) .
C4 C5 1.381(7) .
C4 H4 0.9500 .
C5 C6 1.395(7) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 O1 1.231(6) .
C7 N1 1.358(6) .
C7 C8 1.520(6) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
N1 H1N 0.89(2) .
C11 C16 1.391(7) .
C11 C12 1.397(7) .
C11 N11 1.412(7) .
C12 C13 1.380(7) .
C12 H12 0.9500 .
C13 C14 1.379(8) .
C13 Br11 1.912(5) .
C14 C15 1.376(8) .
C14 H14 0.9500 .
C15 C16 1.390(8) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 O11 1.237(6) .
C17 N11 1.352(6) .
C17 C18 1.498(7) .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
N11 H11N 0.88(2) .
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
N1 H1N O11 0.89(2) 1.94(2) 2.823(5) 172(5) 4_585
N11 H11N O1 0.88(2) 2.02(2) 2.892(5) 175(6) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139045555
