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#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/74/2227468.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_2227468
loop_
_publ_author_name
'Manvizhi, K.'
'Ranjith, S.'
'Parthiban, K.'
'Rajagopal, G.'
'SubbiahPandi, A.'
_publ_section_title
;
 2-Bromo-4-chloro-6-{(E)-[4-(diethylamino)phenyl]iminomethyl}phenol
;
_journal_coeditor_code           GW2086
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2422
_journal_paper_doi               10.1107/S1600536810033738
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H18 Br Cl N2 O'
_chemical_formula_moiety         'C17 H18 Br Cl N2 O'
_chemical_formula_sum            'C17 H18 Br Cl N2 O'
_chemical_formula_weight         381.69
_chemical_name_systematic
;
2-Bromo-4-chloro-6-{(E)-[4-(diethylamino)phenyl]iminomethyl}phenol
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.418(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3427(3)
_cell_length_b                   10.9204(3)
_cell_length_c                   14.3869(4)
_cell_measurement_reflns_used    4383
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.9
_cell_measurement_theta_min      1.9
_cell_volume                     1658.99(8)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and  PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω 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  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19985
_diffrn_reflns_theta_full        28.91
_diffrn_reflns_theta_max         28.91
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    2.642
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.283
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         4383
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0337
_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)+(0.0389P)²+0.3262P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0875
_reflns_number_gt                2797
_reflns_number_total             4383
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            gw2086.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227468
_cod_database_fobs_code          2227468
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_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
C C1 -0.10155(19) 0.32018(18) 0.54970(15) 0.0458(5) Uani d . 1 . .
H H1 -0.1023 0.2923 0.6106 0.055 Uiso calc R 1 . .
C C2 -0.17812(19) 0.41572(19) 0.50175(15) 0.0443(5) Uani d . 1 . .
C C3 -0.17718(19) 0.45989(18) 0.41258(15) 0.0456(5) Uani d . 1 . .
H H3 -0.2285 0.5256 0.3812 0.055 Uiso calc R 1 . .
C C4 -0.09947(18) 0.40567(19) 0.37050(14) 0.0434(5) Uani d . 1 . .
C C5 -0.02201(17) 0.30769(18) 0.41549(14) 0.0412(4) Uani d . 1 . .
C C6 -0.02323(17) 0.26536(17) 0.50738(14) 0.0398(4) Uani d . 1 . .
C C7 0.05636(18) 0.16390(18) 0.55862(15) 0.0450(5) Uani d . 1 . .
H H7 0.0544 0.1382 0.6197 0.054 Uiso calc R 1 . .
C C8 0.20773(17) 0.01035(17) 0.57157(15) 0.0393(4) Uani d . 1 . .
C C9 0.28861(19) -0.03587(18) 0.52790(14) 0.0443(5) Uani d . 1 . .
H H9 0.2875 -0.0019 0.4683 0.053 Uiso calc R 1 . .
C C10 0.37053(19) -0.13055(19) 0.56995(14) 0.0457(5) Uani d . 1 . .
H H10 0.4238 -0.1589 0.5385 0.055 Uiso calc R 1 . .
C C11 0.37521(17) -0.18518(17) 0.65933(14) 0.0393(4) Uani d . 1 . .
C C12 0.29288(18) -0.13766(18) 0.70294(15) 0.0446(5) Uani d . 1 . .
H H12 0.2933 -0.1712 0.7625 0.054 Uiso calc R 1 . .
C C13 0.21127(18) -0.04266(18) 0.66006(16) 0.0441(5) Uani d . 1 . .
H H13 0.1577 -0.0136 0.6910 0.053 Uiso calc R 1 . .
C C14 0.5476(2) -0.3221(2) 0.66057(16) 0.0530(5) Uani d . 1 . .
H H14A 0.5074 -0.3263 0.5885 0.064 Uiso calc R 1 . .
H H14B 0.5745 -0.4042 0.6846 0.064 Uiso calc R 1 . .
C C15 0.6624(2) -0.2420(3) 0.6864(2) 0.0701(7) Uani d . 1 . .
H H15A 0.6367 -0.1591 0.6672 0.105 Uiso calc R 1 . .
H H15B 0.7150 -0.2701 0.6515 0.105 Uiso calc R 1 . .
H H15C 0.7091 -0.2454 0.7570 0.105 Uiso calc R 1 . .
C C16 0.4686(2) -0.3271(2) 0.79959(16) 0.0576(6) Uani d . 1 . .
H H16A 0.5081 -0.4072 0.8084 0.069 Uiso calc R 1 . .
H H16B 0.3851 -0.3373 0.8026 0.069 Uiso calc R 1 . .
C C17 0.5454(2) -0.2467(3) 0.88435(17) 0.0756(8) Uani d . 1 . .
H H17A 0.6295 -0.2386 0.8840 0.113 Uiso calc R 1 . .
H H17B 0.5494 -0.2826 0.9463 0.113 Uiso calc R 1 . .
H H17C 0.5066 -0.1674 0.8771 0.113 Uiso calc R 1 . .
N N1 0.12906(14) 0.10877(15) 0.52225(12) 0.0432(4) Uani d . 1 . .
N N2 0.45430(15) -0.28149(15) 0.70127(12) 0.0462(4) Uani d . 1 . .
Cl Cl1 -0.27823(7) 0.48188(6) 0.55421(5) 0.07030(19) Uani d . 1 . .
Br Br1 -0.09834(3) 0.46511(3) 0.248320(18) 0.07298(12) Uani d . 1 . .
O O1 0.04963(14) 0.25578(15) 0.37088(11) 0.0584(4) Uani d . 1 . .
H H1A 0.0942 0.2028 0.4074 0.088 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'
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'
Br Br -0.2901 2.4595 '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
C2 C1 C6 . . 119.89(19) ?
C2 C1 H1 . . 120.1 ?
C6 C1 H1 . . 120.1 ?
C1 C2 C3 . . 121.14(19) ?
C1 C2 Cl1 . . 119.54(16) ?
C3 C2 Cl1 . . 119.32(16) ?
C4 C3 C2 . . 119.05(18) ?
C4 C3 H3 . . 120.5 ?
C2 C3 H3 . . 120.5 ?
C3 C4 C5 . . 121.78(19) ?
C3 C4 Br1 . . 119.25(15) ?
C5 C4 Br1 . . 118.96(15) ?
O1 C5 C4 . . 119.85(18) ?
O1 C5 C6 . . 122.04(17) ?
C4 C5 C6 . . 118.11(18) ?
C1 C6 C5 . . 120.02(18) ?
C1 C6 C7 . . 119.20(18) ?
C5 C6 C7 . . 120.78(18) ?
N1 C7 C6 . . 121.83(19) ?
N1 C7 H7 . . 119.1 ?
C6 C7 H7 . . 119.1 ?
C9 C8 C13 . . 117.61(18) ?
C9 C8 N1 . . 116.88(18) ?
C13 C8 N1 . . 125.51(19) ?
C10 C9 C8 . . 121.93(19) ?
C10 C9 H9 . . 119.0 ?
C8 C9 H9 . . 119.0 ?
C9 C10 C11 . . 121.17(19) ?
C9 C10 H10 . . 119.4 ?
C11 C10 H10 . . 119.4 ?
N2 C11 C12 . . 121.54(18) ?
N2 C11 C10 . . 122.01(18) ?
C12 C11 C10 . . 116.44(17) ?
C13 C12 C11 . . 121.82(19) ?
C13 C12 H12 . . 119.1 ?
C11 C12 H12 . . 119.1 ?
C12 C13 C8 . . 121.03(19) ?
C12 C13 H13 . . 119.5 ?
C8 C13 H13 . . 119.5 ?
N2 C14 C15 . . 114.65(19) ?
N2 C14 H14A . . 108.6 ?
C15 C14 H14A . . 108.6 ?
N2 C14 H14B . . 108.6 ?
C15 C14 H14B . . 108.6 ?
H14A C14 H14B . . 107.6 ?
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 C16 C17 . . 114.7(2) ?
N2 C16 H16A . . 108.6 ?
C17 C16 H16A . . 108.6 ?
N2 C16 H16B . . 108.6 ?
C17 C16 H16B . . 108.6 ?
H16A C16 H16B . . 107.6 ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C7 N1 C8 . . 122.49(18) ?
C11 N2 C16 . . 120.96(17) ?
C11 N2 C14 . . 120.81(17) ?
C16 N2 C14 . . 116.70(16) ?
C5 O1 H1A . . 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
C1 C2 . 1.372(3) ?
C1 C6 . 1.383(3) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.374(3) ?
C2 Cl1 . 1.734(2) ?
C3 C4 . 1.373(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.386(3) ?
C4 Br1 . 1.878(2) ?
C5 O1 . 1.332(2) ?
C5 C6 . 1.405(3) ?
C6 C7 . 1.449(3) ?
C7 N1 . 1.277(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.383(3) ?
C8 C13 . 1.386(3) ?
C8 N1 . 1.412(2) ?
C9 C10 . 1.374(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.401(3) ?
C10 H10 . 0.9300 ?
C11 N2 . 1.371(2) ?
C11 C12 . 1.401(3) ?
C12 C13 . 1.377(3) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 N2 . 1.453(3) ?
C14 C15 . 1.499(3) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 N2 . 1.452(3) ?
C16 C17 . 1.497(3) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
O1 H1A . 0.8200 ?
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
O1 H1A N1 1 0.82 1.86 2.588(2) 147
C16 H16A Cg2 2_646 0.96 2.90 3.814(2) 157
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
C6 C1 C2 C3 . . . . -1.1(3) ?
C6 C1 C2 Cl1 . . . . 178.74(15) ?
C1 C2 C3 C4 . . . . 1.0(3) ?
Cl1 C2 C3 C4 . . . . -178.80(15) ?
C2 C3 C4 C5 . . . . 0.0(3) ?
C2 C3 C4 Br1 . . . . 179.70(15) ?
C3 C4 C5 O1 . . . . 178.33(19) ?
Br1 C4 C5 O1 . . . . -1.4(3) ?
C3 C4 C5 C6 . . . . -0.9(3) ?
Br1 C4 C5 C6 . . . . 179.36(14) ?
C2 C1 C6 C5 . . . . 0.1(3) ?
C2 C1 C6 C7 . . . . -179.53(18) ?
O1 C5 C6 C1 . . . . -178.37(18) ?
C4 C5 C6 C1 . . . . 0.9(3) ?
O1 C5 C6 C7 . . . . 1.3(3) ?
C4 C5 C6 C7 . . . . -179.49(18) ?
C1 C6 C7 N1 . . . . 178.95(18) ?
C5 C6 C7 N1 . . . . -0.7(3) ?
C13 C8 C9 C10 . . . . -0.3(3) ?
N1 C8 C9 C10 . . . . 179.17(18) ?
C8 C9 C10 C11 . . . . 0.3(3) ?
C9 C10 C11 N2 . . . . 178.53(18) ?
C9 C10 C11 C12 . . . . -0.3(3) ?
N2 C11 C12 C13 . . . . -178.59(18) ?
C10 C11 C12 C13 . . . . 0.3(3) ?
C11 C12 C13 C8 . . . . -0.2(3) ?
C9 C8 C13 C12 . . . . 0.2(3) ?
N1 C8 C13 C12 . . . . -179.17(18) ?
C6 C7 N1 C8 . . . . 179.57(17) ?
C9 C8 N1 C7 . . . . -175.52(18) ?
C13 C8 N1 C7 . . . . 3.9(3) ?
C12 C11 N2 C16 . . . . -8.6(3) ?
C10 C11 N2 C16 . . . . 172.58(19) ?
C12 C11 N2 C14 . . . . -174.04(18) ?
C10 C11 N2 C14 . . . . 7.2(3) ?
C17 C16 N2 C11 . . . . -74.1(2) ?
C17 C16 N2 C14 . . . . 91.9(2) ?
C15 C14 N2 C11 . . . . 76.5(2) ?
C15 C14 N2 C16 . . . . -89.5(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745858
2 PubChem 136628729
