#------------------------------------------------------------------------------
#$Date: 2022-06-02 00:55:45 +0300 (Thu, 02 Jun 2022) $
#$Revision: 275719 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/01/7130166.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_7130166
loop_
_publ_author_name
'Devi, Lalita'
'Kumar, Prashant'
'Kant, Ruchir'
'Rastogi, Namrata'
_publ_section_title
;
 Exploiting the umpolung reactivity of diazo groups: direct access to
 triazolyl-azaarenes from azaarenes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01897G
_journal_year                    2022
_chemical_formula_sum            'C13 H10 Br N3 O2'
_chemical_formula_weight         320.15
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2022-02-07 deposited with the CCDC.	2022-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                72.27(5)
_cell_angle_beta                 88.36(9)
_cell_angle_gamma                75.68(6)
_cell_formula_units_Z            2
_cell_length_a                   7.692(6)
_cell_length_b                   7.901(2)
_cell_length_c                   11.323(6)
_cell_measurement_reflns_used    665
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.8
_cell_measurement_theta_min      7.1
_cell_volume                     634.3(7)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1058
_diffrn_reflns_av_sigmaI/netI    0.0713
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12288
_diffrn_reflns_theta_full        68.77
_diffrn_reflns_theta_max         68.77
_diffrn_reflns_theta_min         7.06
_diffrn_source_current           0.6
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    4.447
_exptl_absorpt_correction_T_max  0.6904
_exptl_absorpt_correction_T_min  0.5016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.039
_refine_diff_density_min         -1.125
_refine_diff_density_rms         0.288
_refine_ls_extinction_coef       0.062(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0545
_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)+(0.1078P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1799
_reflns_number_gt                1672
_reflns_number_total             2281
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2cc01897g2.cif
_cod_data_source_block           xxx
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_refine_ls_hydrogen_treatment' value 'Constr' was changed
to 'constr' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        634.3(6)
_cod_database_code               7130166
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.06453(8) -0.27198(7) 1.38002(5) 0.0606(4) Uani 1 1 d . . .
C1 C 0.9753(6) -0.0261(6) 1.2784(4) 0.0416(11) Uani 1 1 d . . .
C2 C 1.0004(7) 0.1136(6) 1.3212(4) 0.0437(11) Uani 1 1 d . . .
H2 H 1.0580 0.0855 1.3983 0.052 Uiso 1 1 calc R . .
C3 C 0.9395(6) 0.2950(6) 1.2488(4) 0.0402(11) Uani 1 1 d . . .
H3 H 0.9563 0.3896 1.2764 0.048 Uiso 1 1 calc R . .
C4 C 0.8517(6) 0.3332(6) 1.1329(4) 0.0354(10) Uani 1 1 d . . .
C5 C 0.8261(6) 0.1921(6) 1.0911(4) 0.0367(10) Uani 1 1 d . . .
C6 C 0.8890(7) 0.0092(6) 1.1668(4) 0.0413(11) Uani 1 1 d . . .
H6 H 0.8719 -0.0867 1.1409 0.050 Uiso 1 1 calc R . .
C7 C 0.7883(6) 0.5186(6) 1.0532(4) 0.0351(10) Uani 1 1 d . . .
C8 C 0.6802(7) 0.4107(6) 0.8979(4) 0.0414(11) Uani 1 1 d . . .
H8 H 0.6236 0.4374 0.8206 0.050 Uiso 1 1 calc R . .
C9 C 0.7358(7) 0.2371(6) 0.9705(4) 0.0427(11) Uani 1 1 d . . .
H9 H 0.7164 0.1431 0.9433 0.051 Uiso 1 1 calc R . .
C10 C 0.6684(6) 0.7386(6) 0.8886(4) 0.0391(11) Uani 1 1 d . . .
C11 C 0.5826(7) 0.8375(6) 0.7622(4) 0.0435(11) Uani 1 1 d . . .
C12 C 0.4692(8) 1.1339(7) 0.6199(5) 0.0521(13) Uani 1 1 d . . .
H12A H 0.3668 1.0946 0.5999 0.063 Uiso 1 1 calc R . .
H12B H 0.5554 1.1273 0.5562 0.063 Uiso 1 1 calc R . .
C13 C 0.4098(8) 1.3286(8) 0.6274(6) 0.0615(15) Uani 1 1 d . . .
H13A H 0.3557 1.4103 0.5487 0.092 Uiso 1 1 calc R . .
H13B H 0.5121 1.3652 0.6479 0.092 Uiso 1 1 calc R . .
H13C H 0.3239 1.3332 0.6902 0.092 Uiso 1 1 calc R . .
N1 N 0.7079(5) 0.5511(5) 0.9392(3) 0.0342(8) Uani 1 1 d . . .
N2 N 0.7973(6) 0.6759(5) 1.0710(4) 0.0424(9) Uani 1 1 d . . .
N3 N 0.7201(6) 0.8136(5) 0.9662(4) 0.0430(10) Uani 1 1 d . . .
O1 O 0.5522(6) 0.7651(5) 0.6913(3) 0.0647(11) Uani 1 1 d . . .
O2 O 0.5512(5) 1.0175(4) 0.7417(3) 0.0497(9) Uani 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 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 121.9(4) . . ?
C6 C1 Br1 119.9(4) . . ?
C2 C1 Br1 118.2(4) . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 118.7(4) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 120.9(4) . . ?
C5 C4 C7 118.0(4) . . ?
C3 C4 C7 121.1(4) . . ?
C4 C5 C6 119.1(4) . . ?
C4 C5 C9 119.3(4) . . ?
C6 C5 C9 121.6(4) . . ?
C1 C6 C5 119.4(4) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
N2 C7 N1 110.7(4) . . ?
N2 C7 C4 129.6(4) . . ?
N1 C7 C4 119.7(4) . . ?
C9 C8 N1 119.3(4) . . ?
C9 C8 H8 120.4 . . ?
N1 C8 H8 120.4 . . ?
C8 C9 C5 121.3(4) . . ?
C8 C9 H9 119.4 . . ?
C5 C9 H9 119.4 . . ?
N3 C10 N1 110.5(4) . . ?
N3 C10 C11 126.3(4) . . ?
N1 C10 C11 123.2(4) . . ?
O1 C11 O2 126.0(5) . . ?
O1 C11 C10 124.4(4) . . ?
O2 C11 C10 109.6(4) . . ?
O2 C12 C13 106.6(5) . . ?
O2 C12 H12A 110.4 . . ?
C13 C12 H12A 110.4 . . ?
O2 C12 H12B 110.4 . . ?
C13 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 N1 C10 104.0(4) . . ?
C7 N1 C8 122.4(4) . . ?
C10 N1 C8 133.5(4) . . ?
C7 N2 N3 106.5(4) . . ?
C10 N3 N2 108.3(4) . . ?
C11 O2 C12 116.1(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.896(5) . ?
C1 C6 1.362(7) . ?
C1 C2 1.389(7) . ?
C2 C3 1.385(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.407(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(6) . ?
C4 C7 1.437(6) . ?
C5 C6 1.407(6) . ?
C5 C9 1.453(7) . ?
C6 H6 0.9300 . ?
C7 N2 1.336(6) . ?
C7 N1 1.371(6) . ?
C8 C9 1.336(7) . ?
C8 N1 1.390(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 N3 1.317(6) . ?
C10 N1 1.374(6) . ?
C10 C11 1.487(7) . ?
C11 O1 1.176(6) . ?
C11 O2 1.329(6) . ?
C12 O2 1.462(6) . ?
C12 C13 1.520(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N2 N3 1.371(5) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.1(8) . . . . ?
Br1 C1 C2 C3 179.0(4) . . . . ?
C1 C2 C3 C4 0.4(7) . . . . ?
C2 C3 C4 C5 0.0(7) . . . . ?
C2 C3 C4 C7 -179.0(4) . . . . ?
C3 C4 C5 C6 0.2(7) . . . . ?
C7 C4 C5 C6 179.2(4) . . . . ?
C3 C4 C5 C9 -179.6(4) . . . . ?
C7 C4 C5 C9 -0.6(7) . . . . ?
C2 C1 C6 C5 1.2(7) . . . . ?
Br1 C1 C6 C5 -178.9(3) . . . . ?
C4 C5 C6 C1 -0.8(7) . . . . ?
C9 C5 C6 C1 179.0(4) . . . . ?
C5 C4 C7 N2 -179.5(5) . . . . ?
C3 C4 C7 N2 -0.5(8) . . . . ?
C5 C4 C7 N1 -0.9(7) . . . . ?
C3 C4 C7 N1 178.1(4) . . . . ?
N1 C8 C9 C5 -0.6(7) . . . . ?
C4 C5 C9 C8 1.4(7) . . . . ?
C6 C5 C9 C8 -178.4(5) . . . . ?
N3 C10 C11 O1 173.1(5) . . . . ?
N1 C10 C11 O1 -5.4(8) . . . . ?
N3 C10 C11 O2 -5.2(7) . . . . ?
N1 C10 C11 O2 176.3(4) . . . . ?
N2 C7 N1 C10 0.0(5) . . . . ?
C4 C7 N1 C10 -178.9(4) . . . . ?
N2 C7 N1 C8 -179.4(4) . . . . ?
C4 C7 N1 C8 1.8(7) . . . . ?
N3 C10 N1 C7 -0.3(5) . . . . ?
C11 C10 N1 C7 178.5(4) . . . . ?
N3 C10 N1 C8 179.0(5) . . . . ?
C11 C10 N1 C8 -2.2(8) . . . . ?
C9 C8 N1 C7 -1.0(7) . . . . ?
C9 C8 N1 C10 179.9(5) . . . . ?
N1 C7 N2 N3 0.3(5) . . . . ?
C4 C7 N2 N3 179.0(4) . . . . ?
N1 C10 N3 N2 0.5(5) . . . . ?
C11 C10 N3 N2 -178.2(4) . . . . ?
C7 N2 N3 C10 -0.5(5) . . . . ?
O1 C11 O2 C12 0.8(8) . . . . ?
C10 C11 O2 C12 179.1(4) . . . . ?
C13 C12 O2 C11 168.1(5) . . . . ?
