#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/68/2226865.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_2226865
loop_
_publ_author_name
'de Lill, Daniel T.'
'de Bettencourt-Dias, Ana'
_publ_section_title
;
 4-Bromo-N²,N²,N⁶,N⁶-tetraethylpyridine-2,6-dicarboxamide
;
_journal_coeditor_code           FL2308
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2124
_journal_paper_doi               10.1107/S1600536810028837
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H22 Br N3 O2'
_chemical_formula_moiety         'C15 H22 Br N3 O2'
_chemical_formula_sum            'C15 H22 Br N3 O2'
_chemical_formula_weight         356.27
_chemical_name_systematic
;
4-Bromo-N²,N²,N⁶,N⁶-tetraethylpyridine-2,6-
dicarboxamide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.7096(4)
_cell_length_b                   8.4987(2)
_cell_length_c                   21.5013(4)
_cell_measurement_reflns_used    4936
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.78
_cell_measurement_theta_min      2.82
_cell_volume                     3236.13(12)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0434
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            23172
_diffrn_reflns_theta_full        26.71
_diffrn_reflns_theta_max         26.71
_diffrn_reflns_theta_min         1.89
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.549
_exptl_absorpt_correction_T_max  0.8518
_exptl_absorpt_correction_T_min  0.6697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.584
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0385
_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)+(0.0375P)²+6.2825P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.1005
_reflns_number_gt                2499
_reflns_number_total             3392
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fl2308.cif
_cod_data_source_block           I
_cod_database_code               2226865
_cod_database_fobs_code          2226865
loop_
_symmetry_equiv_pos_as_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_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
Br Br1 0.122569(19) 0.65446(4) 0.436078(17) 0.02253(12) Uani d . 1 . .
N N1 0.02418(15) 0.1655(3) 0.38110(12) 0.0146(6) Uani d . 1 . .
C C2 0.13042(19) 0.3352(4) 0.39707(14) 0.0152(7) Uani d . 1 . .
H H2 0.1835 0.3507 0.3959 0.018 Uiso calc R 1 . .
C C6 -0.10501(18) 0.2584(4) 0.39805(14) 0.0157(7) Uani d . 1 . .
C C3 0.08262(19) 0.4540(4) 0.41694(15) 0.0166(7) Uani d . 1 . .
C C4 0.00592(19) 0.4288(4) 0.41939(14) 0.0164(7) Uani d . 1 . .
H H4 -0.0277 0.5091 0.4327 0.020 Uiso calc R 1 . .
C C5 -0.02047(17) 0.2821(4) 0.40168(14) 0.0126(6) Uani d . 1 . .
C C1 0.09906(18) 0.1947(4) 0.37915(14) 0.0133(7) Uani d . 1 . .
C C7 0.14800(18) 0.0595(4) 0.35846(15) 0.0165(7) Uani d . 1 . .
C C9 -0.26126(18) 0.1403(4) 0.46580(16) 0.0214(8) Uani d . 1 . .
H H9A -0.2419 0.0830 0.5020 0.032 Uiso calc R 1 . .
H H9B -0.3144 0.1130 0.4592 0.032 Uiso calc R 1 . .
H H9C -0.2568 0.2538 0.4731 0.032 Uiso calc R 1 . .
C C15 0.2606(2) -0.0792(5) 0.25542(17) 0.0318(10) Uani d . 1 . .
H H15A 0.2525 -0.0110 0.2193 0.048 Uiso calc R 1 . .
H H15B 0.2899 -0.1718 0.2428 0.048 Uiso calc R 1 . .
H H15C 0.2885 -0.0212 0.2874 0.048 Uiso calc R 1 . .
C C14 0.1854(2) -0.1311(4) 0.28117(17) 0.0261(8) Uani d . 1 . .
H H14A 0.1579 -0.1914 0.2490 0.031 Uiso calc R 1 . .
H H14B 0.1939 -0.2017 0.3171 0.031 Uiso calc R 1 . .
C C13 0.0897(2) 0.0736(4) 0.25344(16) 0.0226(8) Uani d . 1 . .
H H13A 0.1166 0.0742 0.2131 0.027 Uiso calc R 1 . .
H H13B 0.0794 0.1843 0.2650 0.027 Uiso calc R 1 . .
C C8 -0.21630(18) 0.0963(4) 0.40922(16) 0.0194(7) Uani d . 1 . .
H H8A -0.2251 -0.0161 0.3996 0.023 Uiso calc R 1 . .
H H8B -0.2343 0.1591 0.3734 0.023 Uiso calc R 1 . .
C C11 -0.0732(2) -0.1413(4) 0.4195(2) 0.0338(10) Uani d . 1 . .
H H11A -0.1167 -0.1810 0.3961 0.051 Uiso calc R 1 . .
H H11B -0.0557 -0.2222 0.4486 0.051 Uiso calc R 1 . .
H H11C -0.0324 -0.1150 0.3905 0.051 Uiso calc R 1 . .
C C10 -0.0960(2) 0.0050(4) 0.45545(17) 0.0218(8) Uani d . 1 . .
H H10A -0.1294 -0.0264 0.4902 0.026 Uiso calc R 1 . .
H H10B -0.0502 0.0534 0.4736 0.026 Uiso calc R 1 . .
C C12 0.0153(2) -0.0114(5) 0.24541(19) 0.0371(10) Uani d . 1 . .
H H12A 0.0249 -0.1224 0.2358 0.056 Uiso calc R 1 . .
H H12B -0.0131 0.0368 0.2113 0.056 Uiso calc R 1 . .
H H12C -0.0140 -0.0037 0.2839 0.056 Uiso calc R 1 . .
N N3 -0.13501(14) 0.1225(3) 0.41736(13) 0.0139(6) Uani d . 1 . .
N N2 0.13906(15) 0.0027(3) 0.30094(12) 0.0172(6) Uani d . 1 . .
O O2 -0.14317(12) 0.3659(3) 0.37517(11) 0.0202(5) Uani d . 1 . .
O O1 0.19438(13) 0.0070(3) 0.39535(10) 0.0209(5) Uani d . 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 N1 C1 . . 116.9(3) ?
C1 C2 C3 . . 118.2(3) ?
C1 C2 H2 . . 120.9 ?
C3 C2 H2 . . 120.9 ?
O2 C6 N3 . . 122.9(3) ?
O2 C6 C5 . . 117.6(3) ?
N3 C6 C5 . . 119.5(3) ?
C4 C3 C2 . . 120.2(3) ?
C4 C3 Br1 . . 120.1(2) ?
C2 C3 Br1 . . 119.7(2) ?
C3 C4 C5 . . 117.5(3) ?
C3 C4 H4 . . 121.2 ?
C5 C4 H4 . . 121.2 ?
N1 C5 C4 . . 123.8(3) ?
N1 C5 C6 . . 117.9(3) ?
C4 C5 C6 . . 117.9(3) ?
N1 C1 C2 . . 123.3(3) ?
N1 C1 C7 . . 115.7(3) ?
C2 C1 C7 . . 120.9(3) ?
O1 C7 N2 . . 123.1(3) ?
O1 C7 C1 . . 118.2(3) ?
N2 C7 C1 . . 118.7(3) ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
N2 C14 C15 . . 112.0(3) ?
N2 C14 H14A . . 109.2 ?
C15 C14 H14A . . 109.2 ?
N2 C14 H14B . . 109.2 ?
C15 C14 H14B . . 109.2 ?
H14A C14 H14B . . 107.9 ?
N2 C13 C12 . . 113.6(3) ?
N2 C13 H13A . . 108.8 ?
C12 C13 H13A . . 108.8 ?
N2 C13 H13B . . 108.8 ?
C12 C13 H13B . . 108.8 ?
H13A C13 H13B . . 107.7 ?
N3 C8 C9 . . 112.7(3) ?
N3 C8 H8A . . 109.1 ?
C9 C8 H8A . . 109.1 ?
N3 C8 H8B . . 109.1 ?
C9 C8 H8B . . 109.1 ?
H8A C8 H8B . . 107.8 ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
N3 C10 C11 . . 113.5(3) ?
N3 C10 H10A . . 108.9 ?
C11 C10 H10A . . 108.9 ?
N3 C10 H10B . . 108.9 ?
C11 C10 H10B . . 108.9 ?
H10A C10 H10B . . 107.7 ?
C13 C12 H12A . . 109.5 ?
C13 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C13 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C6 N3 C8 . . 118.9(3) ?
C6 N3 C10 . . 125.1(3) ?
C8 N3 C10 . . 115.2(3) ?
C7 N2 C14 . . 118.8(3) ?
C7 N2 C13 . . 124.3(3) ?
C14 N2 C13 . . 116.7(3) ?
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
Br1 C3 . 1.890(3) ?
N1 C5 . 1.343(4) ?
N1 C1 . 1.350(4) ?
C2 C1 . 1.372(4) ?
C2 C3 . 1.385(4) ?
C2 H2 . 0.9500 ?
C6 O2 . 1.238(4) ?
C6 N3 . 1.338(4) ?
C6 C5 . 1.513(4) ?
C3 C4 . 1.376(5) ?
C4 C5 . 1.385(4) ?
C4 H4 . 0.9500 ?
C1 C7 . 1.506(4) ?
C7 O1 . 1.226(4) ?
C7 N2 . 1.337(4) ?
C9 C8 . 1.501(5) ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C15 C14 . 1.509(5) ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C14 N2 . 1.465(4) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C13 N2 . 1.474(4) ?
C13 C12 . 1.512(5) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C8 N3 . 1.467(4) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C11 C10 . 1.519(5) ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
C10 N3 . 1.465(4) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
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
C2 H2 O1 8_665 0.95 2.54 3.429(4) 156
C8 H8A O2 8_555 0.99 2.59 3.250(4) 124
C8 H8B O2 . 0.99 2.39 2.732(4) 100
C9 H9A O1 5_556 0.98 2.48 3.447(4) 168
C9 H9B O2 8_555 0.98 2.87 3.479(4) 121
C10 H10A O1 5_556 0.99 2.72 3.652(4) 157
C13 H13A O2 3_545 0.99 2.63 3.415(4) 135
C14 H14A O2 3_545 0.99 2.73 3.444(4) 130
C15 H15A O2 3_545 0.98 2.99 3.525(4) 115
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745613
2 PubChem 12047832
