#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/66/1516638.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_1516638
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_common            '[2-BrPyH][Cl]''
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.274(3)
_cell_length_b                   4.4396(9)
_cell_length_c                   10.581(2)
_cell_measurement_reflns_used    1036
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      22.98
_cell_measurement_theta_min      2.85
_cell_volume                     670.5(2)
_computing_cell_refinement       'Bruker SAINT+ v. 6.36a'
_computing_data_collection       'Bruker SMART v. 5.626'
_computing_data_reduction        'Bruker SAINT+ v. 6.36a'
_computing_molecular_graphics    'XP, Bruker SHELXTL v. 6.12'
_computing_publication_material  'XCIF, Bruker SHELXTL v. 6.12'
_computing_structure_refinement  'XL, Bruker SHELXTL v. 6.12'
_computing_structure_solution    'XS, Bruker SHELXTL v. 6.12'
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker/Siemens SMART APEX'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_av_sigmaI/netI    0.0913
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6162
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.85
_diffrn_standards_decay_%        <0.01
_exptl_absorpt_coefficient_mu    6.418
_exptl_absorpt_correction_T_max  0.724
_exptl_absorpt_correction_T_min  0.190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (SAINT+, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.926
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1538
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0463
_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)+(0.0058P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0982
_reflns_number_gt                961
_reflns_number_total             1538
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp0660684si20060917_081838.cif
_cod_data_source_block           bt623
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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      Pca2(1)
_cod_database_code               1516638
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
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
Cl1 Cl 0.40284(11) 0.8932(4) 0.83215(19) 0.0528(4) Uani 1 1 d .
Br1 Br 0.37479(5) 0.75139(18) 0.52741(14) 0.0536(2) Uani 1 1 d .
N1 N 0.4342(4) 0.7177(11) 0.2800(5) 0.0428(13) Uani 1 1 d .
H1 H 0.4763 0.8401 0.3073 0.051 Uiso 1 1 calc R
C2 C 0.3684(4) 0.6157(17) 0.3585(6) 0.0407(15) Uani 1 1 d .
C3 C 0.3008(4) 0.4255(13) 0.3200(7) 0.0462(15) Uani 1 1 d .
H3 H 0.2541 0.3598 0.3748 0.055 Uiso 1 1 calc R
C5 C 0.3715(5) 0.4356(19) 0.1135(6) 0.053(2) Uani 1 1 d .
H5 H 0.3734 0.3734 0.0297 0.064 Uiso 1 1 calc R
C4 C 0.3040(5) 0.3310(16) 0.1937(6) 0.0527(19) Uani 1 1 d .
H4 H 0.2595 0.1951 0.1641 0.063 Uiso 1 1 calc R
C6 C 0.4352(5) 0.6314(16) 0.1590(6) 0.0477(17) Uani 1 1 d .
H6 H 0.4808 0.7080 0.1051 0.057 Uiso 1 1 calc R
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
Cl1 0.0561(10) 0.0551(10) 0.0472(8) -0.0019(11) 0.0016(10) -0.0117(9)
Br1 0.0548(4) 0.0621(4) 0.0438(3) -0.0053(4) 0.0071(4) 0.0015(4)
N1 0.043(4) 0.038(3) 0.048(3) -0.005(2) 0.002(3) -0.006(3)
C2 0.039(4) 0.041(3) 0.042(4) 0.000(3) 0.000(3) 0.010(3)
C3 0.037(4) 0.045(4) 0.056(4) -0.002(4) -0.003(4) -0.006(3)
C5 0.051(5) 0.062(6) 0.046(4) -0.011(4) 0.002(3) 0.003(4)
C4 0.041(5) 0.058(5) 0.059(4) 0.001(4) -0.015(4) -0.001(3)
C6 0.047(5) 0.049(4) 0.047(4) -0.004(4) 0.013(3) 0.003(4)
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 120.5(6)
C2 N1 H1 119.8
C6 N1 H1 119.8
N1 C2 C3 122.0(6)
N1 C2 Br1 116.6(5)
C3 C2 Br1 121.4(5)
C2 C3 C4 116.9(7)
C2 C3 H3 121.5
C4 C3 H3 121.5
C6 C5 C4 118.3(7)
C6 C5 H5 120.8
C4 C5 H5 120.8
C5 C4 C3 120.9(7)
C5 C4 H4 119.6
C3 C4 H4 119.6
N1 C6 C5 121.3(7)
N1 C6 H6 119.3
C5 C6 H6 119.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C2 1.888(6)
N1 C2 1.333(8)
N1 C6 1.336(8)
N1 H1 0.8600
C2 C3 1.346(8)
C3 C4 1.402(10)
C3 H3 0.9300
C5 C6 1.347(10)
C5 C4 1.365(9)
C5 H5 0.9300
C4 H4 0.9300
C6 H6 0.9300
