#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/14/4021441.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_4021441
loop_
_publ_author_name
'Ibrahim Eryazici'
'Charles N. Moorefield'
'Semih Durmus'
'George R. Newkome'
_publ_section_title
;
 Synthesis and Single-Crystal X-ray Characterization of
 4,4' '-Functionalized 4'-(4-Bromophenyl)-2,2':6',2' '-terpyridines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1009
_journal_page_last               1014
_journal_paper_doi               10.1021/jo052036l
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C23 H16 Br N3 O2'
_chemical_formula_sum            'C23 H16 Br N3 O2'
_chemical_formula_weight         446.30
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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            4
_cell_length_a                   17.428(2)
_cell_length_b                   5.5538(7)
_cell_length_c                   19.492(3)
_cell_measurement_reflns_used    5503
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      2.56
_cell_volume                     1886.6(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0536
_diffrn_reflns_av_sigmaI/netI    0.0788
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15289
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    2.205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.931
_refine_diff_density_min         -0.761
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.022(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4506
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0099P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0878
_reflns_number_gt                4094
_reflns_number_total             4506
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo052036lsi20050928_013454.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4021441
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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
Br1 Br 0.920413(14) -0.57042(4) -0.05677(2) 0.02307(9) Uani 1 1 d
O1 O 0.54716(14) 1.0795(4) 0.33005(11) 0.0238(5) Uani 1 1 d
O2 O 0.48394(11) 1.2647(3) 0.24416(10) 0.0204(4) Uani 1 1 d
N1 N 0.71971(14) 0.3954(4) 0.26392(12) 0.0172(5) Uani 1 1 d
N2 N 0.86250(16) 0.0819(4) 0.36279(13) 0.0256(6) Uani 1 1 d
N3 N 0.60915(16) 0.5974(4) 0.11870(13) 0.0207(5) Uani 1 1 d
C1 C 0.69160(17) 0.3974(5) 0.20031(15) 0.0181(6) Uani 1 1 d
C2 C 0.71610(16) 0.2376(5) 0.14938(15) 0.0178(5) Uani 1 1 d
C3 C 0.77332(17) 0.0717(5) 0.16459(15) 0.0179(6) Uani 1 1 d
C4 C 0.80173(18) 0.0696(5) 0.23127(16) 0.0197(6) Uani 1 1 d
C5 C 0.77358(17) 0.2328(5) 0.27922(14) 0.0185(6) Uani 1 1 d
C6 C 0.80750(16) 0.2440(5) 0.34952(13) 0.0176(5) Uani 1 1 d
C7 C 0.78668(18) 0.4230(5) 0.39591(16) 0.0204(6) Uani 1 1 d
C8 C 0.82497(18) 0.4356(5) 0.45815(14) 0.0222(7) Uani 1 1 d
C9 C 0.88181(18) 0.2715(6) 0.47180(16) 0.0245(6) Uani 1 1 d
C10 C 0.8982(2) 0.0979(6) 0.42328(16) 0.0273(7) Uani 1 1 d
C11 C 0.63405(18) 0.5879(5) 0.18386(15) 0.0179(6) Uani 1 1 d
C12 C 0.60892(17) 0.7484(5) 0.23374(15) 0.0187(6) Uani 1 1 d
C13 C 0.55685(19) 0.9252(5) 0.21593(16) 0.0185(6) Uani 1 1 d
C14 C 0.53126(17) 0.9372(5) 0.14887(16) 0.0207(6) Uani 1 1 d
C15 C 0.55887(19) 0.7700(6) 0.10241(16) 0.0243(6) Uani 1 1 d
C16 C 0.53006(17) 1.0946(5) 0.27034(15) 0.0189(6) Uani 1 1 d
C17 C 0.4524(2) 1.4340(5) 0.29310(17) 0.0229(6) Uani 1 1 d
C18 C 0.80647(16) -0.0881(5) 0.11079(15) 0.0179(6) Uani 1 1 d
C19 C 0.80659(19) -0.0174(6) 0.04206(16) 0.0214(6) Uani 1 1 d
C20 C 0.84135(18) -0.1591(5) -0.00773(16) 0.0225(6) Uani 1 1 d
C21 C 0.87575(16) -0.3727(5) 0.01132(15) 0.0195(6) Uani 1 1 d
C22 C 0.87565(18) -0.4484(5) 0.07904(16) 0.0199(6) Uani 1 1 d
C23 C 0.84097(17) -0.3058(5) 0.12867(14) 0.0189(6) Uani 1 1 d
H2 H 0.6937(16) 0.247(5) 0.1070(17) 0.004(7) Uiso 1 1 d
H4 H 0.843(2) -0.035(5) 0.245(2) 0.017(8) Uiso 1 1 d
H7 H 0.7455(18) 0.536(5) 0.3807(16) 0.005(7) Uiso 1 1 d
H8 H 0.802(2) 0.558(5) 0.493(2) 0.020(9) Uiso 1 1 d
H9 H 0.9103(19) 0.269(6) 0.514(2) 0.027(9) Uiso 1 1 d
H10 H 0.942(2) -0.005(7) 0.432(3) 0.046(10) Uiso 1 1 d
H12 H 0.6282(16) 0.739(5) 0.2705(16) 0.001(7) Uiso 1 1 d
H14 H 0.495(2) 1.067(6) 0.138(2) 0.029(10) Uiso 1 1 d
H15 H 0.542(2) 0.771(6) 0.059(2) 0.027(9) Uiso 1 1 d
H19 H 0.7853(16) 0.133(5) 0.0296(16) 0.005(7) Uiso 1 1 d
H20 H 0.846(2) -0.105(6) -0.047(3) 0.054(13) Uiso 1 1 d
H22 H 0.897(3) -0.596(8) 0.094(3) 0.062(16) Uiso 1 1 d
H23 H 0.842(2) -0.361(7) 0.178(2) 0.030(9) Uiso 1 1 d
H17A H 0.424(2) 1.549(7) 0.268(3) 0.033(12) Uiso 1 1 d
H17B H 0.495(2) 1.520(7) 0.317(2) 0.030(9) Uiso 1 1 d
H17C H 0.4119(18) 1.345(7) 0.328(2) 0.021(8) Uiso 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'
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
C16 O2 C17 115.7(2)
C1 N1 C5 118.1(2)
C10 N2 C6 117.3(3)
C15 N3 C11 117.7(3)
N1 C1 C2 122.9(3)
N1 C1 C11 116.9(2)
C2 C1 C11 120.2(3)
C3 C2 C1 119.2(3)
C2 C3 C4 117.4(3)
C2 C3 C18 121.5(3)
C4 C3 C18 121.0(3)
C3 C4 C5 119.8(3)
N1 C5 C4 122.5(3)
N1 C5 C6 117.0(2)
C4 C5 C6 120.3(3)
N2 C6 C7 122.7(3)
N2 C6 C5 115.6(2)
C7 C6 C5 121.5(3)
C8 C7 C6 118.6(3)
C9 C8 C7 118.9(3)
C8 C9 C10 118.7(3)
N2 C10 C9 123.7(3)
N3 C11 C12 122.3(3)
N3 C11 C1 116.6(2)
C12 C11 C1 121.1(3)
C13 C12 C11 119.2(3)
C12 C13 C14 118.9(3)
C12 C13 C16 118.4(3)
C14 C13 C16 122.7(3)
C13 C14 C15 118.3(3)
N3 C15 C14 123.6(3)
O1 C16 O2 124.4(3)
O1 C16 C13 124.4(3)
O2 C16 C13 111.2(2)
C23 C18 C19 118.9(3)
C23 C18 C3 120.5(3)
C19 C18 C3 120.6(3)
C20 C19 C18 120.8(3)
C21 C20 C19 119.3(3)
C20 C21 C22 121.1(3)
C20 C21 Br1 119.3(2)
C22 C21 Br1 119.5(2)
C21 C22 C23 119.4(3)
C22 C23 C18 120.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C21 1.890(3)
O1 C16 1.204(4)
O2 C16 1.341(3)
O2 C17 1.448(3)
N1 C1 1.333(4)
N1 C5 1.336(4)
N2 C10 1.336(4)
N2 C6 1.340(4)
N3 C15 1.337(4)
N3 C11 1.343(4)
C1 C2 1.398(4)
C1 C11 1.493(4)
C2 C3 1.390(4)
C3 C4 1.391(4)
C3 C18 1.490(4)
C4 C5 1.391(4)
C5 C6 1.494(4)
C6 C7 1.392(4)
C7 C8 1.386(4)
C8 C9 1.372(4)
C9 C10 1.380(4)
C11 C12 1.390(4)
C12 C13 1.381(4)
C13 C14 1.383(4)
C13 C16 1.493(4)
C14 C15 1.384(4)
C18 C23 1.395(4)
C18 C19 1.396(4)
C19 C20 1.388(4)
C20 C21 1.380(4)
C21 C22 1.385(4)
C22 C23 1.389(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9721563
2 PubChem 11546784
