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#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/86/7218603.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_7218603
loop_
_publ_author_name
'Wang, Shu-Wen'
'Guo, Wei-Si'
'Wen, Li-Rong'
'Li, Ming'
_publ_section_title
;
 A new approach to pyridines through the reactions of methyl ketones with
 1,2,4-triazines
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA11294F
_journal_year                    2014
_chemical_formula_sum            'C17 H12 Br N'
_chemical_formula_weight         310.19
_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                 116.108(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.441(2)
_cell_length_b                   13.358(3)
_cell_length_c                   11.148(2)
_cell_measurement_reflns_used    1896
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      22.15
_cell_measurement_theta_min      2.65
_cell_volume                     1396.2(5)
_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      294(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0541
_diffrn_reflns_av_sigmaI/netI    0.0587
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7911
_diffrn_reflns_theta_full        26.43
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    2.928
_exptl_absorpt_correction_T_max  0.7201
_exptl_absorpt_correction_T_min  0.5651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.068
_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     172
_refine_ls_number_reflns         2850
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0412
_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)+(0.0556P)²+0.1512P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1188
_reflns_number_gt                1652
_reflns_number_total             2850
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra11294f2.cif
_cod_data_source_block           70320b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed
to 'constr' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'NONE' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1396.3(5)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7218603
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
Br1 Br 0.97089(5) 1.24218(3) 0.24937(4) 0.0615(2) Uani 1 1 d .
N1 N 0.6058(4) 0.7265(2) 0.5152(3) 0.0545(9) Uani 1 1 d .
C1 C 0.8252(4) 1.0603(3) 0.4617(4) 0.0497(10) Uani 1 1 d .
H1 H 0.8180 1.0650 0.5417 0.060 Uiso 1 1 calc R
C2 C 0.8808(4) 1.1399(3) 0.4214(4) 0.0502(10) Uani 1 1 d .
H2 H 0.9098 1.1977 0.4729 0.060 Uiso 1 1 calc R
C3 C 0.8927(4) 1.1324(2) 0.3037(3) 0.0432(9) Uani 1 1 d .
C4 C 0.8480(4) 1.0482(3) 0.2253(3) 0.0461(9) Uani 1 1 d .
H4 H 0.8550 1.0445 0.1451 0.055 Uiso 1 1 calc R
C5 C 0.7924(4) 0.9687(3) 0.2675(3) 0.0449(9) Uani 1 1 d .
H5 H 0.7629 0.9113 0.2152 0.054 Uiso 1 1 calc R
C6 C 0.7798(4) 0.9735(3) 0.3868(3) 0.0402(9) Uani 1 1 d .
C7 C 0.7201(4) 0.8881(3) 0.4314(3) 0.0423(9) Uani 1 1 d .
C8 C 0.6477(4) 0.9036(3) 0.5098(4) 0.0523(10) Uani 1 1 d .
H8 H 0.6354 0.9677 0.5355 0.063 Uiso 1 1 calc R
C9 C 0.5953(5) 0.8213(3) 0.5478(4) 0.0607(11) Uani 1 1 d .
H9 H 0.5484 0.8327 0.6007 0.073 Uiso 1 1 calc R
C10 C 0.6765(4) 0.7114(3) 0.4402(3) 0.0428(9) Uani 1 1 d .
C11 C 0.7321(4) 0.7904(3) 0.3971(3) 0.0429(9) Uani 1 1 d .
H11 H 0.7784 0.7773 0.3441 0.051 Uiso 1 1 calc R
C12 C 0.6895(4) 0.6063(3) 0.4058(3) 0.0440(9) Uani 1 1 d .
C13 C 0.5856(4) 0.5363(3) 0.3925(4) 0.0528(10) Uani 1 1 d .
H13 H 0.5075 0.5560 0.4060 0.063 Uiso 1 1 calc R
C14 C 0.5959(5) 0.4380(3) 0.3596(4) 0.0623(12) Uani 1 1 d .
H14 H 0.5256 0.3923 0.3520 0.075 Uiso 1 1 calc R
C15 C 0.7097(5) 0.4074(3) 0.3381(4) 0.0611(12) Uani 1 1 d .
H15 H 0.7157 0.3415 0.3141 0.073 Uiso 1 1 calc R
C16 C 0.8146(5) 0.4749(3) 0.3524(4) 0.0611(12) Uani 1 1 d .
H16 H 0.8926 0.4544 0.3392 0.073 Uiso 1 1 calc R
C17 C 0.8050(5) 0.5730(3) 0.3864(4) 0.0546(11) Uani 1 1 d .
H17 H 0.8773 0.6177 0.3964 0.066 Uiso 1 1 calc R
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'
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
C9 N1 C10 116.3(3)
C2 C1 C6 122.0(3)
C2 C1 H1 119.0
C6 C1 H1 119.0
C3 C2 C1 118.9(3)
C3 C2 H2 120.5
C1 C2 H2 120.5
C4 C3 C2 121.2(3)
C4 C3 Br1 120.2(3)
C2 C3 Br1 118.7(3)
C3 C4 C5 119.1(3)
C3 C4 H4 120.4
C5 C4 H4 120.4
C4 C5 C6 121.1(3)
C4 C5 H5 119.4
C6 C5 H5 119.4
C1 C6 C5 117.6(3)
C1 C6 C7 121.5(3)
C5 C6 C7 120.9(3)
C11 C7 C8 116.9(3)
C11 C7 C6 122.0(3)
C8 C7 C6 121.1(3)
C9 C8 C7 118.2(4)
C9 C8 H8 120.9
C7 C8 H8 120.9
N1 C9 C8 125.6(4)
N1 C9 H9 117.2
C8 C9 H9 117.2
N1 C10 C11 121.8(3)
N1 C10 C12 116.1(3)
C11 C10 C12 122.1(3)
C7 C11 C10 121.3(3)
C7 C11 H11 119.4
C10 C11 H11 119.4
C17 C12 C13 117.3(4)
C17 C12 C10 122.0(3)
C13 C12 C10 120.7(4)
C14 C13 C12 121.3(4)
C14 C13 H13 119.4
C12 C13 H13 119.4
C15 C14 C13 120.3(4)
C15 C14 H14 119.8
C13 C14 H14 119.8
C16 C15 C14 119.4(4)
C16 C15 H15 120.3
C14 C15 H15 120.3
C15 C16 C17 120.4(4)
C15 C16 H16 119.8
C17 C16 H16 119.8
C16 C17 C12 121.3(4)
C16 C17 H17 119.3
C12 C17 H17 119.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C3 1.902(3)
N1 C9 1.335(5)
N1 C10 1.352(5)
C1 C2 1.378(5)
C1 C6 1.385(5)
C1 H1 0.9300
C2 C3 1.375(4)
C2 H2 0.9300
C3 C4 1.374(5)
C4 C5 1.388(5)
C4 H4 0.9300
C5 C6 1.395(5)
C5 H5 0.9300
C6 C7 1.486(5)
C7 C11 1.382(5)
C7 C8 1.400(5)
C8 C9 1.375(5)
C8 H8 0.9300
C9 H9 0.9300
C10 C11 1.389(5)
C10 C12 1.478(5)
C11 H11 0.9300
C12 C17 1.388(5)
C12 C13 1.390(5)
C13 C14 1.379(5)
C13 H13 0.9300
C14 C15 1.374(6)
C14 H14 0.9300
C15 C16 1.372(6)
C15 H15 0.9300
C16 C17 1.380(5)
C16 H16 0.9300
C17 H17 0.9300
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
C6 C1 C2 C3 -0.6(6)
C1 C2 C3 C4 1.2(6)
C1 C2 C3 Br1 -179.5(3)
C2 C3 C4 C5 -1.2(6)
Br1 C3 C4 C5 179.5(3)
C3 C4 C5 C6 0.7(6)
C2 C1 C6 C5 0.1(6)
C2 C1 C6 C7 180.0(4)
C4 C5 C6 C1 -0.2(6)
C4 C5 C6 C7 180.0(3)
C1 C6 C7 C11 -151.0(4)
C5 C6 C7 C11 28.8(5)
C1 C6 C7 C8 29.5(6)
C5 C6 C7 C8 -150.7(4)
C11 C7 C8 C9 0.6(6)
C6 C7 C8 C9 -179.9(4)
C10 N1 C9 C8 1.1(6)
C7 C8 C9 N1 -0.7(7)
C9 N1 C10 C11 -1.3(5)
C9 N1 C10 C12 179.2(3)
C8 C7 C11 C10 -0.9(5)
C6 C7 C11 C10 179.6(3)
N1 C10 C11 C7 1.3(6)
C12 C10 C11 C7 -179.3(3)
N1 C10 C12 C17 -149.9(4)
C11 C10 C12 C17 30.6(5)
N1 C10 C12 C13 29.7(5)
C11 C10 C12 C13 -149.7(4)
C17 C12 C13 C14 -0.8(6)
C10 C12 C13 C14 179.6(3)
C12 C13 C14 C15 -0.6(6)
C13 C14 C15 C16 1.4(6)
C14 C15 C16 C17 -0.9(7)
C15 C16 C17 C12 -0.5(6)
C13 C12 C17 C16 1.3(6)
C10 C12 C17 C16 -179.1(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139199411
