#------------------------------------------------------------------------------
#$Date: 2025-07-05 13:10:14 +0300 (Sat, 05 Jul 2025) $
#$Revision: 300370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/17/1571765.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_1571765
loop_
_publ_author_name
'Saravanan, Dhandayutham'
'Ponraj, C.'
'Khamrang, Themmila'
'Hemamalini, Madhukar'
'Antony, G. Jerald Maria'
_publ_section_title
;
 2-(10-Bromoanthracen-9-yl)-N-phenylaniline
;
_journal_coeditor_code           HB4471
_journal_issue                   5
_journal_name_full               IUCrData
_journal_page_first              x240475
_journal_paper_doi               10.1107/S2414314624004759
_journal_volume                  9
_journal_year                    2024
_chemical_formula_iupac          'C26 H18 Br N'
_chemical_formula_moiety         'C26 H18 Br N'
_chemical_formula_sum            'C26 H18 Br N'
_chemical_formula_weight         424.32
_chemical_name_systematic
;
2-(10-Bromoanthracen-9-yl)-N-phenylaniline
;
_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-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 106.809(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0619(17)
_cell_length_b                   7.6891(10)
_cell_length_c                   20.475(3)
_cell_measurement_reflns_used    3999
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.372
_cell_measurement_theta_min      3.368
_cell_volume                     1968.5(5)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2012)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Agilent Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12046
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.368
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.099
_exptl_absorpt_correction_T_max  0.5716
_exptl_absorpt_correction_T_min  0.4323
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(CrysAlis RED; Agilent, 2012)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.806
_refine_diff_density_min         -1.402
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3999
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0494
_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)+(0.0558P)²+1.6534P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1293
_reflns_number_gt                3115
_reflns_number_total             3999
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4471.cif
_cod_data_source_block           I
_cod_original_cell_volume        1968.6(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1571765
#BEGIN Tags that were not found in dictionaries:
_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_min   0.432
_shelx_estimated_absorpt_t_max   0.572
#END Tags that were not found in dictionaries
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_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 -0.02528(3) -0.04566(6) 0.34351(2) 0.0715(2) Uani d 1 . .
N N1 0.4598(2) 0.3135(4) 0.41519(18) 0.0577(9) Uani d 1 . .
C C3 0.1079(2) 0.2407(4) 0.40118(14) 0.0324(6) Uani d 1 . .
C C12 0.1886(2) 0.3680(4) 0.40287(14) 0.0315(6) Uani d 1 . .
C C11 0.2396(2) 0.3735(4) 0.35115(14) 0.0309(6) Uani d 1 . .
C C5 0.1305(2) 0.1255(4) 0.29426(14) 0.0321(6) Uani d 1 . .
C C10 0.2127(2) 0.2523(4) 0.29757(14) 0.0306(6) Uani d 1 . .
C C4 0.0816(2) 0.1236(4) 0.34678(15) 0.0346(6) Uani d 1 . .
C C15 0.3228(2) 0.5092(4) 0.35332(15) 0.0338(6) Uani d 1 . .
C C9 0.2637(2) 0.2517(4) 0.24464(15) 0.0396(7) Uani d 1 . .
H H9 0.317747 0.331703 0.246104 0.048 Uiso calc 1 . .
C C20 0.4302(2) 0.4749(4) 0.38369(16) 0.0374(7) Uani d 1 . .
C C2 0.0601(3) 0.2382(4) 0.45579(15) 0.0424(7) Uani d 1 . .
H H2 0.007271 0.156905 0.455513 0.051 Uiso calc 1 . .
C C8 0.2351(3) 0.1373(4) 0.19247(16) 0.0467(8) Uani d 1 . .
H H8 0.269377 0.139879 0.158491 0.056 Uiso calc 1 . .
C C21 0.5558(2) 0.2265(4) 0.41906(17) 0.0410(7) Uani d 1 . .
C C13 0.2159(3) 0.4878(4) 0.45853(16) 0.0426(7) Uani d 1 . .
H H13 0.267045 0.573083 0.460148 0.051 Uiso calc 1 . .
C C6 0.1034(3) 0.0083(4) 0.23773(16) 0.0426(7) Uani d 1 . .
H H6 0.049834 -0.073800 0.234413 0.051 Uiso calc 1 . .
C C7 0.1544(3) 0.0148(4) 0.18900(17) 0.0487(8) Uani d 1 . .
H H7 0.135678 -0.063095 0.152715 0.058 Uiso calc 1 . .
C C16 0.2937(3) 0.6726(4) 0.32505(18) 0.0478(8) Uani d 1 . .
H H16 0.221626 0.697953 0.305740 0.057 Uiso calc 1 . .
C C26 0.6048(3) 0.1311(4) 0.47645(18) 0.0482(8) Uani d 1 . .
H H26 0.576252 0.129337 0.513136 0.058 Uiso calc 1 . .
C C18 0.4752(3) 0.7621(4) 0.35375(18) 0.0501(8) Uani d 1 . .
H H18 0.526590 0.845360 0.353300 0.060 Uiso calc 1 . .
C C1 0.0911(3) 0.3530(5) 0.50787(16) 0.0484(8) Uani d 1 . .
H H1 0.060381 0.347710 0.543532 0.058 Uiso calc 1 . .
C C19 0.5059(3) 0.6027(4) 0.38339(19) 0.0492(8) Uani d 1 . .
H H19 0.578117 0.579804 0.403488 0.059 Uiso calc 1 . .
C C22 0.6002(3) 0.2280(5) 0.36512(19) 0.0512(8) Uani d 1 . .
H H22 0.567577 0.291351 0.325915 0.061 Uiso calc 1 . .
C C17 0.3693(3) 0.7984(4) 0.32496(19) 0.0545(9) Uani d 1 . .
H H17 0.348321 0.906707 0.305481 0.065 Uiso calc 1 . .
C C14 0.1681(3) 0.4789(5) 0.50894(17) 0.0497(8) Uani d 1 . .
H H14 0.187045 0.558049 0.544786 0.060 Uiso calc 1 . .
C C23 0.6920(3) 0.1364(5) 0.3695(2) 0.0620(10) Uani d 1 . .
H H23 0.721646 0.139989 0.333358 0.074 Uiso calc 1 . .
C C25 0.6966(3) 0.0379(5) 0.4793(3) 0.0678(12) Uani d 1 . .
H H25 0.729331 -0.027472 0.517943 0.081 Uiso calc 1 . .
C C24 0.7402(3) 0.0409(5) 0.4254(3) 0.0717(12) Uani d 1 . .
H H24 0.801947 -0.021919 0.427468 0.086 Uiso calc 1 . .
H H55 0.425(3) 0.265(6) 0.435(2) 0.073(14) Uiso 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'
Br Br -0.2901 2.4595 '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'
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
C20 N1 C21 . . 124.8(3) ?
C20 N1 H55 . . 122(3) ?
C21 N1 H55 . . 113(3) ?
C4 C3 C2 . . 123.6(3) ?
C4 C3 C12 . . 118.0(2) ?
C2 C3 C12 . . 118.4(3) ?
C11 C12 C13 . . 121.2(3) ?
C11 C12 C3 . . 120.6(3) ?
C13 C12 C3 . . 118.2(3) ?
C10 C11 C12 . . 120.1(2) ?
C10 C11 C15 . . 120.1(2) ?
C12 C11 C15 . . 119.8(2) ?
C4 C5 C6 . . 123.7(3) ?
C4 C5 C10 . . 118.1(2) ?
C6 C5 C10 . . 118.2(3) ?
C11 C10 C9 . . 121.9(3) ?
C11 C10 C5 . . 120.2(2) ?
C9 C10 C5 . . 118.0(3) ?
C3 C4 C5 . . 123.0(3) ?
C3 C4 Br1 . . 118.7(2) ?
C5 C4 Br1 . . 118.3(2) ?
C20 C15 C16 . . 118.6(3) ?
C20 C15 C11 . . 120.8(3) ?
C16 C15 C11 . . 120.6(3) ?
C8 C9 C10 . . 121.3(3) ?
C8 C9 H9 . . 119.4 ?
C10 C9 H9 . . 119.4 ?
C15 C20 C19 . . 119.4(3) ?
C15 C20 N1 . . 118.9(3) ?
C19 C20 N1 . . 121.7(3) ?
C1 C2 C3 . . 120.6(3) ?
C1 C2 H2 . . 119.7 ?
C3 C2 H2 . . 119.7 ?
C9 C8 C7 . . 120.7(3) ?
C9 C8 H8 . . 119.6 ?
C7 C8 H8 . . 119.6 ?
C26 C21 C22 . . 119.1(3) ?
C26 C21 N1 . . 119.3(3) ?
C22 C21 N1 . . 121.5(3) ?
C14 C13 C12 . . 120.8(3) ?
C14 C13 H13 . . 119.6 ?
C12 C13 H13 . . 119.6 ?
C7 C6 C5 . . 121.0(3) ?
C7 C6 H6 . . 119.5 ?
C5 C6 H6 . . 119.5 ?
C6 C7 C8 . . 120.8(3) ?
C6 C7 H7 . . 119.6 ?
C8 C7 H7 . . 119.6 ?
C17 C16 C15 . . 121.5(3) ?
C17 C16 H16 . . 119.2 ?
C15 C16 H16 . . 119.2 ?
C21 C26 C25 . . 119.7(4) ?
C21 C26 H26 . . 120.2 ?
C25 C26 H26 . . 120.2 ?
C17 C18 C19 . . 120.2(3) ?
C17 C18 H18 . . 119.9 ?
C19 C18 H18 . . 119.9 ?
C2 C1 C14 . . 121.1(3) ?
C2 C1 H1 . . 119.5 ?
C14 C1 H1 . . 119.5 ?
C18 C19 C20 . . 120.8(3) ?
C18 C19 H19 . . 119.6 ?
C20 C19 H19 . . 119.6 ?
C23 C22 C21 . . 120.1(3) ?
C23 C22 H22 . . 119.9 ?
C21 C22 H22 . . 119.9 ?
C18 C17 C16 . . 119.4(3) ?
C18 C17 H17 . . 120.3 ?
C16 C17 H17 . . 120.3 ?
C13 C14 C1 . . 120.9(3) ?
C13 C14 H14 . . 119.5 ?
C1 C14 H14 . . 119.5 ?
C24 C23 C22 . . 121.3(4) ?
C24 C23 H23 . . 119.3 ?
C22 C23 H23 . . 119.3 ?
C24 C25 C26 . . 120.7(4) ?
C24 C25 H25 . . 119.7 ?
C26 C25 H25 . . 119.7 ?
C23 C24 C25 . . 119.1(4) ?
C23 C24 H24 . . 120.4 ?
C25 C24 H24 . . 120.4 ?
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 C4 . 1.896(3) ?
N1 C20 . 1.401(4) ?
N1 C21 . 1.404(4) ?
N1 H55 . 0.78(4) ?
C3 C4 . 1.396(4) ?
C3 C2 . 1.430(4) ?
C3 C12 . 1.432(4) ?
C12 C11 . 1.405(4) ?
C12 C13 . 1.429(4) ?
C11 C10 . 1.405(4) ?
C11 C15 . 1.497(4) ?
C5 C4 . 1.400(4) ?
C5 C6 . 1.428(4) ?
C5 C10 . 1.437(4) ?
C10 C9 . 1.427(4) ?
C15 C20 . 1.386(4) ?
C15 C16 . 1.390(4) ?
C9 C8 . 1.351(5) ?
C9 H9 . 0.9300 ?
C20 C19 . 1.395(4) ?
C2 C1 . 1.353(4) ?
C2 H2 . 0.9300 ?
C8 C7 . 1.400(5) ?
C8 H8 . 0.9300 ?
C21 C26 . 1.376(5) ?
C21 C22 . 1.388(5) ?
C13 C14 . 1.353(5) ?
C13 H13 . 0.9300 ?
C6 C7 . 1.352(5) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C16 C17 . 1.383(5) ?
C16 H16 . 0.9300 ?
C26 C25 . 1.385(5) ?
C26 H26 . 0.9300 ?
C18 C17 . 1.366(5) ?
C18 C19 . 1.375(5) ?
C18 H18 . 0.9300 ?
C1 C14 . 1.392(5) ?
C1 H1 . 0.9300 ?
C19 H19 . 0.9300 ?
C22 C23 . 1.371(5) ?
C22 H22 . 0.9300 ?
C17 H17 . 0.9300 ?
C14 H14 . 0.9300 ?
C23 C24 . 1.352(6) ?
C23 H23 . 0.9300 ?
C25 C24 . 1.381(6) ?
C25 H25 . 0.9300 ?
C24 H24 . 0.9300 ?
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
C17 H17 Cg3 1_565 0.93 2.77 3.598(4) 148
C18 H18 Cg5 1_565 0.93 2.85 3.661(4) 146
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
C4 C3 C12 C11 . . . . -0.2(4) ?
C2 C3 C12 C11 . . . . 178.7(3) ?
C4 C3 C12 C13 . . . . -179.9(3) ?
C2 C3 C12 C13 . . . . -1.0(4) ?
C13 C12 C11 C10 . . . . 178.9(3) ?
C3 C12 C11 C10 . . . . -0.8(4) ?
C13 C12 C11 C15 . . . . -1.1(4) ?
C3 C12 C11 C15 . . . . 179.2(2) ?
C12 C11 C10 C9 . . . . -179.0(3) ?
C15 C11 C10 C9 . . . . 1.0(4) ?
C12 C11 C10 C5 . . . . 1.9(4) ?
C15 C11 C10 C5 . . . . -178.1(2) ?
C4 C5 C10 C11 . . . . -2.0(4) ?
C6 C5 C10 C11 . . . . 178.1(3) ?
C4 C5 C10 C9 . . . . 178.8(2) ?
C6 C5 C10 C9 . . . . -1.0(4) ?
C2 C3 C4 C5 . . . . -178.8(3) ?
C12 C3 C4 C5 . . . . 0.0(4) ?
C2 C3 C4 Br1 . . . . 1.3(4) ?
C12 C3 C4 Br1 . . . . -179.9(2) ?
C6 C5 C4 C3 . . . . -179.1(3) ?
C10 C5 C4 C3 . . . . 1.1(4) ?
C6 C5 C4 Br1 . . . . 0.8(4) ?
C10 C5 C4 Br1 . . . . -179.03(19) ?
C10 C11 C15 C20 . . . . -86.9(3) ?
C12 C11 C15 C20 . . . . 93.1(3) ?
C10 C11 C15 C16 . . . . 93.3(4) ?
C12 C11 C15 C16 . . . . -86.7(4) ?
C11 C10 C9 C8 . . . . -178.3(3) ?
C5 C10 C9 C8 . . . . 0.8(4) ?
C16 C15 C20 C19 . . . . -1.8(5) ?
C11 C15 C20 C19 . . . . 178.5(3) ?
C16 C15 C20 N1 . . . . 176.9(3) ?
C11 C15 C20 N1 . . . . -2.8(5) ?
C21 N1 C20 C15 . . . . 148.5(3) ?
C21 N1 C20 C19 . . . . -32.9(5) ?
C4 C3 C2 C1 . . . . 178.5(3) ?
C12 C3 C2 C1 . . . . -0.3(4) ?
C10 C9 C8 C7 . . . . -0.3(5) ?
C20 N1 C21 C26 . . . . 144.7(4) ?
C20 N1 C21 C22 . . . . -38.2(5) ?
C11 C12 C13 C14 . . . . -178.4(3) ?
C3 C12 C13 C14 . . . . 1.3(5) ?
C4 C5 C6 C7 . . . . -179.1(3) ?
C10 C5 C6 C7 . . . . 0.8(4) ?
C5 C6 C7 C8 . . . . -0.2(5) ?
C9 C8 C7 C6 . . . . 0.0(5) ?
C20 C15 C16 C17 . . . . 1.9(5) ?
C11 C15 C16 C17 . . . . -178.4(3) ?
C22 C21 C26 C25 . . . . -0.4(5) ?
N1 C21 C26 C25 . . . . 176.8(3) ?
C3 C2 C1 C14 . . . . 1.6(5) ?
C17 C18 C19 C20 . . . . 1.0(5) ?
C15 C20 C19 C18 . . . . 0.4(5) ?
N1 C20 C19 C18 . . . . -178.3(3) ?
C26 C21 C22 C23 . . . . -0.5(5) ?
N1 C21 C22 C23 . . . . -177.5(3) ?
C19 C18 C17 C16 . . . . -0.9(6) ?
C15 C16 C17 C18 . . . . -0.5(6) ?
C12 C13 C14 C1 . . . . -0.1(5) ?
C2 C1 C14 C13 . . . . -1.3(5) ?
C21 C22 C23 C24 . . . . 1.1(6) ?
C21 C26 C25 C24 . . . . 0.6(6) ?
C22 C23 C24 C25 . . . . -0.9(6) ?
C26 C25 C24 C23 . . . . 0.0(6) ?
