#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/66/1516646.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_1516646
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
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 95.83(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.3924(9)
_cell_length_b                   8.1794(16)
_cell_length_c                   9.4338(19)
_cell_measurement_temperature    295(2)
_cell_volume                     337.18(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0513
_diffrn_reflns_av_sigmaI/netI    0.0609
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3613
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    6.381
_exptl_absorpt_correction_T_max  0.8316
_exptl_absorpt_correction_T_min  0.2505
_exptl_crystal_density_diffrn    1.915
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             188
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.774
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.136
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     43
_refine_ls_number_reflns         822
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0459
_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)+(0.0500P)²+0.4057P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1229
_reflns_number_gt                634
_reflns_number_total             822
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp0660684si20060917_081838.cif
_cod_data_source_block           bt538
_cod_database_code               1516646
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -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
Br4 Br 0.63738(17) 0.2500 1.03346(9) 0.0496(3) Uani 1 2 d S
C4 C 0.8260(15) 0.2500 0.8604(8) 0.0387(15) Uani 1 2 d S
N1 N 1.1308(14) 0.2500 0.6289(7) 0.0498(16) Uani 1 2 d S
H1A H 1.2326 0.2500 0.5557 0.060 Uiso 1 2 calc SR
C3 C 0.8979(12) 0.1024(6) 0.8009(6) 0.0465(12) Uani 1 1 d .
H3A H 0.8412 0.0037 0.8394 0.056 Uiso 1 1 calc R
C2 C 1.0561(12) 0.1069(7) 0.6827(6) 0.0501(13) Uani 1 1 d .
H2A H 1.1109 0.0100 0.6403 0.060 Uiso 1 1 calc R
Cl Cl 0.4794(4) 0.2500 1.3694(2) 0.0440(4) Uani 1 2 d S
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
Br4 0.0505(5) 0.0464(5) 0.0535(5) 0.000 0.0133(3) 0.000
C4 0.038(4) 0.035(3) 0.042(4) 0.000 -0.003(3) 0.000
N1 0.044(4) 0.062(4) 0.044(4) 0.000 0.010(3) 0.000
C3 0.053(3) 0.030(2) 0.056(3) 0.001(2) 0.002(3) 0.001(2)
C2 0.054(3) 0.044(3) 0.053(3) -0.012(2) 0.004(3) 0.010(2)
Cl 0.0473(10) 0.0359(9) 0.0509(10) 0.000 0.0160(8) 0.000
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C3 C4 C3 121.8(7) . 4_565
C3 C4 Br4 119.1(4) . .
C3 C4 Br4 119.1(4) 4_565 .
C2 N1 C2 123.3(7) . 4_565
C2 N1 H1A 118.3 . .
C2 N1 H1A 118.3 4_565 .
C2 C3 C4 117.6(5) . .
C2 C3 H3A 121.2 . .
C4 C3 H3A 121.2 . .
N1 C2 C3 119.8(5) . .
N1 C2 H2A 120.1 . .
C3 C2 H2A 120.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br4 C4 1.904(7) .
C4 C3 1.381(6) .
C4 C3 1.381(6) 4_565
N1 C2 1.330(7) .
N1 C2 1.330(7) 4_565
N1 H1A 0.8600 .
C3 C2 1.373(8) .
C3 H3A 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 Cl 0.86 2.16 3.016(7) 178.9 1_654
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
C3 C4 C3 C2 2.6(10) 4_565
Br4 C4 C3 C2 -174.8(4) .
C2 N1 C2 C3 -1.0(11) 4_565
C4 C3 C2 N1 -0.8(8) .
