#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:20:24 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301776 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/66/1516644.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_1516644
loop_
_publ_author_name
'Awwadi, Firas F.'
'Willett, Roger D.'
'Peterson, Kirk A.'
'Twamley, Brendan'
_publ_section_title
;
 The nature of halogen...halide synthons: theoretical and crystallographic
 studies.
;
_journal_issue                   12
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              2319
_journal_page_last               2328
_journal_paper_doi               10.1021/jp0660684
_journal_volume                  111
_journal_year                    2007
_chemical_formula_sum            'C5 H5 Br Cl N'
_chemical_formula_weight         194.46
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_cell_angle_alpha                83.626(13)
_cell_angle_beta                 77.592(19)
_cell_angle_gamma                86.920(15)
_cell_formula_units_Z            2
_cell_length_a                   4.9079(13)
_cell_length_b                   7.8016(9)
_cell_length_c                   9.2523(12)
_cell_measurement_reflns_used    23
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      14.81
_cell_measurement_theta_min      5.07
_cell_volume                     343.69(11)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω 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  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0633
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1560
_diffrn_reflns_theta_full        24.42
_diffrn_reflns_theta_max         24.42
_diffrn_reflns_theta_min         2.27
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    6.260
_exptl_absorpt_correction_T_max  0.8909
_exptl_absorpt_correction_T_min  0.5051
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.879
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             188
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.646
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0718P)²+0.0367P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1229
_reflns_number_gt                857
_reflns_number_total             1129
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp0660684si20060917_081838.cif
_cod_data_source_block           fa225a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/ACS/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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1516644
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
Cl3 Cl -0.1723(4) 1.2723(3) 0.9845(2) 0.0652(6) Uani 1 1 d .
N1 N -0.6286(13) 1.3452(8) 0.6851(7) 0.0556(16) Uani 1 1 d .
H1A H -0.7150 1.4313 0.6465 0.067 Uiso 1 1 calc R
C5 C -0.5185(16) 1.0516(10) 0.7051(8) 0.0519(18) Uani 1 1 d .
H5A H -0.5337 0.9417 0.6783 0.062 Uiso 1 1 calc R
C4 C -0.3620(14) 1.0755(8) 0.8074(8) 0.0464(17) Uani 1 1 d .
H4A H -0.2669 0.9825 0.8481 0.056 Uiso 1 1 calc R
C3 C -0.3472(13) 1.2372(8) 0.8490(7) 0.0411(15) Uani 1 1 d .
C6 C -0.6519(16) 1.1900(12) 0.6426(8) 0.059(2) Uani 1 1 d .
H6A H -0.7564 1.1759 0.5722 0.071 Uiso 1 1 calc R
C2 C -0.4799(15) 1.3751(9) 0.7835(9) 0.0524(19) Uani 1 1 d .
H2A H -0.4658 1.4865 0.8075 0.063 Uiso 1 1 calc R
Br Br -0.03002(15) 1.30085(8) 1.34972(8) 0.0510(3) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl3 0.0621(12) 0.0802(14) 0.0601(12) -0.0193(10) -0.0207(10) -0.0067(10)
N1 0.053(4) 0.056(4) 0.051(4) 0.011(3) -0.008(3) 0.018(3)
C5 0.064(5) 0.049(4) 0.047(4) -0.011(3) -0.018(4) -0.001(4)
C4 0.050(4) 0.034(3) 0.052(4) -0.001(3) -0.010(3) 0.011(3)
C3 0.040(4) 0.042(4) 0.040(4) -0.004(3) -0.006(3) 0.002(3)
C6 0.056(5) 0.082(6) 0.040(4) -0.003(4) -0.013(4) 0.004(4)
C2 0.053(4) 0.039(4) 0.058(5) -0.004(3) 0.004(4) 0.004(3)
Br 0.0559(5) 0.0375(4) 0.0653(5) -0.0062(3) -0.0272(4) 0.0082(3)
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'
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
C2 N1 C6 124.0(6)
C2 N1 H1A 118.0
C6 N1 H1A 118.0
C6 C5 C4 119.9(7)
C6 C5 H5A 120.0
C4 C5 H5A 120.0
C3 C4 C5 119.5(6)
C3 C4 H4A 120.2
C5 C4 H4A 120.2
C4 C3 C2 119.7(7)
C4 C3 Cl3 121.5(5)
C2 C3 Cl3 118.8(6)
N1 C6 C5 118.4(7)
N1 C6 H6A 120.8
C5 C6 H6A 120.8
N1 C2 C3 118.4(7)
N1 C2 H2A 120.8
C3 C2 H2A 120.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl3 C3 1.717(7)
N1 C2 1.329(10)
N1 C6 1.332(11)
N1 H1A 0.8600
C5 C6 1.370(11)
C5 C4 1.373(10)
C5 H5A 0.9300
C4 C3 1.369(9)
C4 H4A 0.9300
C3 C2 1.378(10)
C6 H6A 0.9300
C2 H2A 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Br 0.86 2.38 3.174(6) 154.3 2_487
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 C5 C4 C3 1.8(11)
C5 C4 C3 C2 -2.6(10)
C5 C4 C3 Cl3 176.0(6)
C2 N1 C6 C5 1.0(11)
C4 C5 C6 N1 -0.9(12)
C6 N1 C2 C3 -1.8(11)
C4 C3 C2 N1 2.6(10)
Cl3 C3 C2 N1 -176.0(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139043657
