#------------------------------------------------------------------------------
#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/19/4031921.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_4031921
loop_
_publ_author_name
'Durel, Vianney'
'Lalli, Claudia'
'Roisnel, Thierry'
'Weghe, Pierre van de'
_publ_section_title
;
 Synergistic Effect of the TiCl4/p-TsOH Promoter System on the Aza-Prins
 Cyclization.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              849
_journal_page_last               859
_journal_paper_doi               10.1021/acs.joc.5b02342
_journal_volume                  81
_journal_year                    2016
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C11 H13 Br Cl N'
_chemical_formula_sum            'C11 H13 Br Cl N'
_chemical_formula_weight         274.58
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      60
_symmetry_space_group_name_Hall  '-P 2n 2c'
_symmetry_space_group_name_H-M   'P c a n'
_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             2014-11-04T12:08:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.4944(6)
_cell_length_b                   17.8095(14)
_cell_length_c                   23.213(3)
_cell_measurement_reflns_used    1393
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.83
_cell_measurement_theta_min      3.51
_cell_measurement_wavelength     0.71073
_cell_volume                     2271.5(4)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
          WinGX publication routines (Farrugia, 2012),
          CRYSCALc (T. Roisnel, local program, 2014)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0783
_diffrn_reflns_av_unetI/netI     0.0736
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            10758
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.51
_exptl_absorpt_coefficient_mu    3.815
_exptl_absorpt_correction_T_max  0.766
_exptl_absorpt_correction_T_min  0.523
_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    1.606
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2592
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0413P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.1052
_reflns_number_gt                1623
_reflns_number_total             2592
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02342_si_002.cif
_cod_data_source_block           VD338
_cod_database_code               4031921
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x, -y, -z+1/2'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x, y, z-1/2'
'x-1/2, -y-1/2, 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
Br1 Br 0.86992(8) 0.15619(2) 0.071755(17) 0.03921(16) Uani 1 1 d .
Cl1 Cl 0.31794(18) 0.00251(5) 0.43252(4) 0.0327(2) Uani 1 1 d .
C1 C 0.8555(7) 0.14579(18) 0.15306(16) 0.0259(8) Uani 1 1 d .
C2 C 0.6634(7) 0.17754(19) 0.18298(17) 0.0285(9) Uani 1 1 d .
H2 H 0.5389 0.2038 0.163 0.034 Uiso 1 1 calc R
C3 C 0.6544(7) 0.17074(18) 0.24239(16) 0.0269(9) Uani 1 1 d .
H3 H 0.5231 0.1928 0.263 0.032 Uiso 1 1 calc R
C4 C 0.8350(6) 0.13207(18) 0.27238(15) 0.0226(8) Uani 1 1 d .
C5 C 1.0249(7) 0.10161(19) 0.24090(16) 0.0277(9) Uani 1 1 d .
H5 H 1.1507 0.0755 0.2606 0.033 Uiso 1 1 calc R
C6 C 1.0363(7) 0.1083(2) 0.18149(16) 0.0302(9) Uani 1 1 d .
H6 H 1.1683 0.0869 0.1607 0.036 Uiso 1 1 calc R
C7 C 0.8183(6) 0.11986(19) 0.33653(15) 0.0231(8) Uani 1 1 d .
H7 H 0.972 0.0953 0.3498 0.028 Uiso 1 1 calc R
N8 N 0.7907(6) 0.19172(15) 0.36762(13) 0.0239(7) Uani 1 1 d D
H8 H 0.891(6) 0.2262(17) 0.3575(17) 0.05 Uiso 1 1 d D
C9 C 0.7927(7) 0.17886(19) 0.43016(15) 0.0269(8) Uani 1 1 d .
H9A H 0.7848 0.2276 0.4506 0.032 Uiso 1 1 calc R
H9B H 0.9461 0.1536 0.4413 0.032 Uiso 1 1 calc R
C10 C 0.5770(7) 0.13044(19) 0.44765(15) 0.0259(9) Uani 1 1 d .
H10A H 0.5811 0.1214 0.4897 0.031 Uiso 1 1 calc R
H10B H 0.4233 0.1568 0.4383 0.031 Uiso 1 1 calc R
C11 C 0.5870(6) 0.05635(18) 0.41596(14) 0.0223(8) Uani 1 1 d .
H11 H 0.7335 0.0278 0.4291 0.027 Uiso 1 1 calc R
C12 C 0.6041(7) 0.06845(18) 0.35174(15) 0.0251(8) Uani 1 1 d .
H12A H 0.4508 0.0912 0.3376 0.03 Uiso 1 1 calc R
H12B H 0.6251 0.0194 0.3323 0.03 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 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'
Cl Cl 0.1484 0.1585 '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
C6 C1 C2 120.8(4)
C6 C1 Br1 119.8(3)
C2 C1 Br1 119.4(3)
C1 C2 C3 119.4(3)
C1 C2 H2 120.3
C3 C2 H2 120.3
C2 C3 C4 121.0(4)
C2 C3 H3 119.5
C4 C3 H3 119.5
C5 C4 C3 117.8(3)
C5 C4 C7 120.7(3)
C3 C4 C7 121.4(3)
C4 C5 C6 121.7(4)
C4 C5 H5 119.1
C6 C5 H5 119.1
C1 C6 C5 119.3(4)
C1 C6 H6 120.4
C5 C6 H6 120.4
N8 C7 C4 111.3(3)
N8 C7 C12 109.1(3)
C4 C7 C12 111.1(3)
N8 C7 H7 108.4
C4 C7 H7 108.4
C12 C7 H7 108.4
C9 N8 C7 110.3(3)
C9 N8 H8 112(3)
C7 N8 H8 115(3)
N8 C9 C10 110.3(3)
N8 C9 H9A 109.6
C10 C9 H9A 109.6
N8 C9 H9B 109.6
C10 C9 H9B 109.6
H9A C9 H9B 108.1
C11 C10 C9 109.7(3)
C11 C10 H10A 109.7
C9 C10 H10A 109.7
C11 C10 H10B 109.7
C9 C10 H10B 109.7
H10A C10 H10B 108.2
C12 C11 C10 111.0(3)
C12 C11 Cl1 109.7(2)
C10 C11 Cl1 109.3(2)
C12 C11 H11 108.9
C10 C11 H11 108.9
Cl1 C11 H11 108.9
C11 C12 C7 111.1(3)
C11 C12 H12A 109.4
C7 C12 H12A 109.4
C11 C12 H12B 109.4
C7 C12 H12B 109.4
H12A C12 H12B 108
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.898(4)
Cl1 C11 1.804(4)
C1 C6 1.367(5)
C1 C2 1.384(5)
C2 C3 1.385(5)
C2 H2 0.95
C3 C4 1.394(5)
C3 H3 0.95
C4 C5 1.384(5)
C4 C7 1.508(5)
C5 C6 1.386(5)
C5 H5 0.95
C6 H6 0.95
C7 N8 1.477(4)
C7 C12 1.532(5)
C7 H7 1
N8 C9 1.470(4)
N8 H8 0.857(18)
C9 C10 1.521(5)
C9 H9A 0.99
C9 H9B 0.99
C10 C11 1.512(5)
C10 H10A 0.99
C10 H10B 0.99
C11 C12 1.509(4)
C11 H11 1
C12 H12A 0.99
C12 H12B 0.99
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 -0.3(5)
Br1 C1 C2 C3 -179.2(3)
C1 C2 C3 C4 -0.4(5)
C2 C3 C4 C5 0.8(5)
C2 C3 C4 C7 -175.8(3)
C3 C4 C5 C6 -0.6(5)
C7 C4 C5 C6 176.1(3)
C2 C1 C6 C5 0.5(5)
Br1 C1 C6 C5 179.4(3)
C4 C5 C6 C1 0.0(5)
C5 C4 C7 N8 127.6(3)
C3 C4 C7 N8 -55.8(4)
C5 C4 C7 C12 -110.6(4)
C3 C4 C7 C12 66.0(4)
C4 C7 N8 C9 -175.9(3)
C12 C7 N8 C9 61.1(4)
C7 N8 C9 C10 -62.9(4)
N8 C9 C10 C11 58.5(4)
C9 C10 C11 C12 -54.3(4)
C9 C10 C11 Cl1 -175.4(2)
C10 C11 C12 C7 54.1(4)
Cl1 C11 C12 C7 175.0(2)
N8 C7 C12 C11 -56.8(4)
C4 C7 C12 C11 -179.9(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139094640
