#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/19/7151916.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_7151916
loop_
_publ_author_name
'Zeghada, Sarah'
'Bentabed-Ababsa, Ghenia'
'Derdour, Aïcha'
'Abdelmounim, Safer'
'Domingo, Luis R.'
'Sáez, José A'
'Roisnel, Thierry'
'Nassar, Ekhlass'
'Mongin, Florence'
_publ_section_title
;
 A combined experimental and theoretical study of the thermal
 cycloaddition of aryl azides with activated alkenes.
;
_journal_issue                   11
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4295
_journal_page_last               4305
_journal_paper_doi               10.1039/c1ob05176h
_journal_volume                  9
_journal_year                    2011
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C11 H10 Br N3 O1'
_chemical_formula_sum            'C11 H10 Br N3 O'
_chemical_formula_weight         280.13
_space_group_IT_number           2
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2010-03-30T14:50:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                86.338(2)
_cell_angle_beta                 81.785(2)
_cell_angle_gamma                89.249(2)
_cell_formula_units_Z            2
_cell_length_a                   5.6105(2)
_cell_length_b                   6.4884(3)
_cell_length_c                   15.2886(7)
_cell_measurement_reflns_used    6661
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      2.7
_cell_measurement_wavelength     0.71073
_cell_volume                     549.71(4)
_computing_cell_refinement       'Bruker SMART (Bruker, 2002)'
_computing_data_collection       'Bruker SAINT (Bruker, 2002)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2002)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
WinGX publication routines (Farrugia, 1999),
CRYSCAL (T. Roisnel, local program)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999))'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8739
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.15
_exptl_absorpt_coefficient_mu    3.720
_exptl_absorpt_correction_T_max  0.458
_exptl_absorpt_correction_T_min  0.238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0192
_refine_ls_R_factor_gt           0.0179
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0182P)²+0.2943P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0446
_refine_ls_wR_factor_ref         0.0452
_reflns_number_gt                2396
_reflns_number_total             2494
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob05176h.txt
_cod_data_source_block           3c
_cod_database_code               7151916
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 1.32058(2) -0.29516(2) 0.474097(9) 0.01666(6) Uani 1 1 d . . .
C2 C 1.1481(3) -0.1265(2) 0.39845(9) 0.0132(3) Uani 1 1 d . . .
C4 C 0.8238(3) -0.0894(2) 0.31221(9) 0.0133(3) Uani 1 1 d . . .
H4 H 0.6909 -0.1451 0.2896 0.016 Uiso 1 1 calc R . .
C3 C 0.9556(3) -0.2124(2) 0.36592(9) 0.0139(3) Uani 1 1 d . . .
H3 H 0.9145 -0.3533 0.3802 0.017 Uiso 1 1 calc R . .
C5 C 0.8886(3) 0.1166(2) 0.29178(9) 0.0118(3) Uani 1 1 d . . .
C6 C 1.0819(3) 0.2021(2) 0.32445(9) 0.0131(3) Uani 1 1 d . . .
H6 H 1.1236 0.3428 0.3099 0.016 Uiso 1 1 calc R . .
C7 C 1.2134(3) 0.0795(2) 0.37852(9) 0.0142(3) Uani 1 1 d . . .
H7 H 1.3457 0.1353 0.4015 0.017 Uiso 1 1 calc R . .
N8 N 0.7425(2) 0.24720(17) 0.24158(8) 0.0116(2) Uani 1 1 d . . .
N9 N 0.6650(2) 0.43352(18) 0.27375(8) 0.0137(2) Uani 1 1 d . . .
N10 N 0.5184(2) 0.51331(18) 0.22208(8) 0.0137(2) Uani 1 1 d . . .
C11 C 0.4977(3) 0.3816(2) 0.15695(9) 0.0127(3) Uani 1 1 d . . .
C12 C 0.6434(3) 0.2101(2) 0.16811(9) 0.0129(3) Uani 1 1 d . . .
C13 C 0.7019(3) 0.0263(2) 0.11502(10) 0.0195(3) Uani 1 1 d . . .
H13A H 0.8764 0.0029 0.1067 0.029 Uiso 1 1 calc R . .
H13B H 0.6472 0.0506 0.0571 0.029 Uiso 1 1 calc R . .
H13C H 0.6206 -0.0955 0.1463 0.029 Uiso 1 1 calc R . .
C14 C 0.3235(3) 0.4205(2) 0.09369(10) 0.0150(3) Uani 1 1 d . . .
C15 C 0.1736(3) 0.6144(2) 0.10253(11) 0.0189(3) Uani 1 1 d . . .
H15A H 0.0552 0.6166 0.0612 0.028 Uiso 1 1 calc R . .
H15B H 0.2783 0.7354 0.089 0.028 Uiso 1 1 calc R . .
H15C H 0.0897 0.6175 0.1632 0.028 Uiso 1 1 calc R . .
O16 O 0.2998(2) 0.29712(17) 0.03838(8) 0.0231(2) 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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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 0.006 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C2 C7 121.85(13) . . ?
C3 C2 Br1 118.44(11) . . ?
C7 C2 Br1 119.69(10) . . ?
C3 C4 C5 119.35(13) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C2 C3 C4 119.11(13) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C6 C5 C4 121.37(13) . . ?
C6 C5 N8 119.16(12) . . ?
C4 C5 N8 119.31(12) . . ?
C7 C6 C5 119.37(13) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C2 118.95(13) . . ?
C6 C7 H7 120.5 . . ?
C2 C7 H7 120.5 . . ?
C12 N8 N9 111.07(11) . . ?
C12 N8 C5 130.07(11) . . ?
N9 N8 C5 118.54(11) . . ?
N10 N9 N8 107.09(11) . . ?
N9 N10 C11 109.27(11) . . ?
N10 C11 C12 109.05(12) . . ?
N10 C11 C14 121.64(12) . . ?
C12 C11 C14 129.02(12) . . ?
N8 C12 C11 103.51(12) . . ?
N8 C12 C13 123.98(13) . . ?
C11 C12 C13 132.44(13) . . ?
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 . . ?
O16 C14 C11 120.89(13) . . ?
O16 C14 C15 122.08(13) . . ?
C11 C14 C15 117.00(12) . . ?
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 . . ?
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 C2 1.8980(14) . ?
C2 C3 1.3891(19) . ?
C2 C7 1.394(2) . ?
C4 C3 1.390(2) . ?
C4 C5 1.3937(19) . ?
C4 H4 0.95 . ?
C3 H3 0.95 . ?
C5 C6 1.3931(19) . ?
C5 N8 1.4342(17) . ?
C6 C7 1.3912(19) . ?
C6 H6 0.95 . ?
C7 H7 0.95 . ?
N8 C12 1.3586(17) . ?
N8 N9 1.3762(16) . ?
N9 N10 1.3003(17) . ?
N10 C11 1.3709(17) . ?
C11 C12 1.3880(19) . ?
C11 C14 1.4787(19) . ?
C12 C13 1.4924(19) . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 O16 1.2227(18) . ?
C14 C15 1.507(2) . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
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
C7 C2 C3 C4 -0.2(2) . . . . ?
Br1 C2 C3 C4 178.43(10) . . . . ?
C5 C4 C3 C2 0.4(2) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C3 C4 C5 N8 -175.65(12) . . . . ?
C4 C5 C6 C7 0.1(2) . . . . ?
N8 C5 C6 C7 175.38(12) . . . . ?
C5 C6 C7 C2 0.1(2) . . . . ?
C3 C2 C7 C6 -0.1(2) . . . . ?
Br1 C2 C7 C6 -178.68(10) . . . . ?
C6 C5 N8 C12 140.32(15) . . . . ?
C4 C5 N8 C12 -44.3(2) . . . . ?
C6 C5 N8 N9 -46.83(18) . . . . ?
C4 C5 N8 N9 128.58(14) . . . . ?
C12 N8 N9 N10 0.29(15) . . . . ?
C5 N8 N9 N10 -173.86(12) . . . . ?
N8 N9 N10 C11 0.36(15) . . . . ?
N9 N10 C11 C12 -0.86(16) . . . . ?
N9 N10 C11 C14 173.52(13) . . . . ?
N9 N8 C12 C11 -0.78(15) . . . . ?
C5 N8 C12 C11 172.50(13) . . . . ?
N9 N8 C12 C13 176.63(13) . . . . ?
C5 N8 C12 C13 -10.1(2) . . . . ?
N10 C11 C12 N8 0.98(15) . . . . ?
C14 C11 C12 N8 -172.87(14) . . . . ?
N10 C11 C12 C13 -176.11(15) . . . . ?
C14 C11 C12 C13 10.0(3) . . . . ?
N10 C11 C14 O16 -176.82(14) . . . . ?
C12 C11 C14 O16 -3.7(2) . . . . ?
N10 C11 C14 C15 1.4(2) . . . . ?
C12 C11 C14 C15 174.61(14) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 740685
2 PubChem 847702
