#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/02/2210290.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2210290
loop_
_publ_author_name
'Faroughi, Masoud'
'Try, Andrew C.'
'Turner, Peter'
_publ_section_title
2,4,8,10-Tetrabromo-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine
_journal_coeditor_code           HK2104
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3893
_journal_page_last               o3894
_journal_paper_doi               10.1107/S1600536806031734
_journal_volume                  62
_journal_year                    2006
_chemical_formula_moiety         'C15 H10 Br4 N2'
_chemical_formula_sum            'C15 H10 Br4 N2'
_chemical_formula_weight         537.89
_chemical_melting_point          498.33
_chemical_name_common
;
Tetrabromo Tröger's base
;
_chemical_name_systematic
;
2,4,8,10-tetrabromo-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine
;
_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                   8.040(3)
_cell_length_b                   12.475(4)
_cell_length_c                   15.331(5)
_cell_measurement_reflns_used    1012
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      3.02
_cell_volume                     1537.7(9)
_computing_cell_refinement       SAINT
_computing_data_collection       'SMART (Bruker, 1995)'
_computing_data_reduction        'SAINT and XPREP (Bruker, 1995)'
_computing_molecular_graphics
;
TEXSAN for Windows (Molecular Structure Corporation, 1998),
Xtal3.6 (Hall et al.,  1999)
ORTEPII (Johnson, 1976)
;
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al. 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13979
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.63
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    10.461
_exptl_absorpt_correction_T_max  0.519
_exptl_absorpt_correction_T_min  0.042
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
[(Coppens et al.,  1965) using XPREP (Bruker, 1995)]
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.476
_exptl_crystal_size_mid          0.303
_exptl_crystal_size_min          0.063
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.659
_refine_ls_abs_structure_details 'Flack (1983), 1686 Friedel pairs'
_refine_ls_abs_structure_Flack   0.004(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3662
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0240
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.02P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0512
_refine_ls_wR_factor_ref         0.0527
_reflns_number_gt                3419
_reflns_number_total             3662
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2104.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Gaussian' changed to 'gaussian'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '498.33K' was changed to '498.33' -
the value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '498.33K' was changed to '498.33' -
the value should be numeric and without a unit
designator.

'_exptl_absorpt_correction_type' value 'Gaussian'
changed to 'gaussian' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2210290
_cod_database_fobs_code          2210290
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Br Br1 0.48729(5) -0.01522(3) 0.26532(2) 0.02456(9) Uani d . 1
Br Br2 0.30256(5) -0.19191(3) 0.59144(2) 0.02592(9) Uani d . 1
Br Br3 0.07020(5) 0.45333(3) 0.56818(2) 0.02194(9) Uani d . 1
Br Br4 -0.26941(4) 0.41528(4) 0.24542(2) 0.02277(9) Uani d . 1
N N1 0.3313(4) 0.3179(3) 0.47455(17) 0.0175(6) Uani d . 1
N N2 0.4448(4) 0.1997(3) 0.36359(18) 0.0177(6) Uani d . 1
C C1 0.3971(4) 0.1088(3) 0.4143(2) 0.0186(7) Uani d . 1
C C2 0.4128(5) 0.0048(3) 0.3821(2) 0.0197(8) Uani d . 1
C C3 0.3808(5) -0.0860(3) 0.4319(2) 0.0211(8) Uani d . 1
H H3 0.3915 -0.1559 0.4078 0.025 Uiso calc R 1
C C4 0.3326(5) -0.0711(3) 0.5182(2) 0.0216(8) Uani d . 1
C C5 0.3095(4) 0.0304(3) 0.5521(2) 0.0202(8) Uani d . 1
H H5 0.2727 0.0386 0.6106 0.024 Uiso calc R 1
C C6 0.3400(4) 0.1211(3) 0.50080(19) 0.0184(7) Uani d . 1
C C7 0.3149(5) 0.2320(3) 0.5397(2) 0.0192(7) Uani d . 1
H H7A 0.2030 0.2359 0.5664 0.023 Uiso calc R 1
H H7B 0.3979 0.2435 0.5865 0.023 Uiso calc R 1
C C8 0.1862(4) 0.3339(3) 0.4224(2) 0.0178(7) Uani d . 1
C C9 0.0536(5) 0.3930(3) 0.45464(19) 0.0174(7) Uani d . 1
C C10 -0.0862(4) 0.4155(3) 0.4050(2) 0.0182(7) Uani d . 1
H H10 -0.1772 0.4544 0.4286 0.022 Uiso calc R 1
C C11 -0.0880(4) 0.3790(3) 0.31942(19) 0.0190(8) Uani d . 1
C C12 0.0398(5) 0.3196(3) 0.28527(19) 0.0182(8) Uani d . 1
H H12 0.0331 0.2941 0.2270 0.022 Uiso calc R 1
C C13 0.1794(5) 0.2964(3) 0.3356(2) 0.0169(7) Uani d . 1
C C14 0.3210(4) 0.2325(3) 0.2975(2) 0.0190(8) Uani d . 1
H H14A 0.2756 0.1676 0.2689 0.023 Uiso calc R 1
H H14B 0.3771 0.2759 0.2522 0.023 Uiso calc R 1
C C15 0.4756(5) 0.2929(3) 0.4195(2) 0.0204(8) Uani d . 1
H H15A 0.5020 0.3557 0.3825 0.024 Uiso calc R 1
H H15B 0.5732 0.2784 0.4571 0.024 Uiso calc R 1
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'
Br Br -0.2901 2.4595 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 N1 C15 110.7(3)
C8 N1 C7 114.2(3)
C15 N1 C7 107.9(3)
C1 N2 C15 110.9(3)
C1 N2 C14 114.3(3)
C15 N2 C14 107.2(3)
C2 C1 C6 117.6(3)
C2 C1 N2 121.5(3)
C6 C1 N2 120.8(4)
C3 C2 C1 123.2(3)
C3 C2 Br1 117.9(3)
C1 C2 Br1 118.9(3)
C2 C3 C4 117.6(4)
C2 C3 H3 121.2
C4 C3 H3 121.2
C5 C4 C3 121.3(4)
C5 C4 Br2 119.2(2)
C3 C4 Br2 119.5(3)
C4 C5 C6 120.4(3)
C4 C5 H5 119.8
C6 C5 H5 119.8
C5 C6 C1 119.8(4)
C5 C6 C7 119.5(3)
C1 C6 C7 120.7(3)
N1 C7 C6 112.6(3)
N1 C7 H7A 109.1
C6 C7 H7A 109.1
N1 C7 H7B 109.1
C6 C7 H7B 109.1
H7A C7 H7B 107.8
C9 C8 C13 118.8(3)
C9 C8 N1 120.2(3)
C13 C8 N1 120.8(3)
C10 C9 C8 122.4(3)
C10 C9 Br3 118.6(3)
C8 C9 Br3 118.9(3)
C9 C10 C11 117.4(3)
C9 C10 H10 121.3
C11 C10 H10 121.3
C12 C11 C10 122.0(3)
C12 C11 Br4 118.4(2)
C10 C11 Br4 119.5(3)
C11 C12 C13 120.3(3)
C11 C12 H12 119.9
C13 C12 H12 119.9
C12 C13 C8 119.0(3)
C12 C13 C14 120.2(3)
C8 C13 C14 120.8(3)
N2 C14 C13 112.8(3)
N2 C14 H14A 109.0
C13 C14 H14A 109.0
N2 C14 H14B 109.0
C13 C14 H14B 109.0
H14A C14 H14B 107.8
N2 C15 N1 111.8(3)
N2 C15 H15A 109.3
N1 C15 H15A 109.3
N2 C15 H15B 109.3
N1 C15 H15B 109.3
H15A C15 H15B 107.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C2 1.905(3)
Br2 C4 1.896(4)
Br3 C9 1.901(3)
Br4 C11 1.903(3)
N1 C8 1.428(4)
N1 C15 1.469(5)
N1 C7 1.470(5)
N2 C1 1.429(5)
N2 C15 1.465(5)
N2 C14 1.478(5)
C1 C2 1.394(5)
C1 C6 1.411(4)
C2 C3 1.390(5)
C3 C4 1.391(5)
C3 H3 0.9500
C4 C5 1.381(5)
C5 C6 1.400(5)
C5 H5 0.9500
C6 C7 1.521(5)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.387(5)
C8 C13 1.411(5)
C9 C10 1.386(5)
C10 C11 1.390(4)
C10 H10 0.9500
C11 C12 1.371(5)
C12 C13 1.393(5)
C12 H12 0.9500
C13 C14 1.509(5)
C14 H14A 0.9900
C14 H14B 0.9900
C15 H15A 0.9900
C15 H15B 0.9900
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
C15 N2 C1 C2 -159.0(3)
C14 N2 C1 C2 79.6(4)
C15 N2 C1 C6 17.7(4)
C14 N2 C1 C6 -103.6(4)
C6 C1 C2 C3 -2.4(6)
N2 C1 C2 C3 174.5(3)
C6 C1 C2 Br1 179.4(3)
N2 C1 C2 Br1 -3.8(5)
C1 C2 C3 C4 -0.7(6)
Br1 C2 C3 C4 177.6(3)
C2 C3 C4 C5 3.0(6)
C2 C3 C4 Br2 -175.6(3)
C3 C4 C5 C6 -2.2(6)
Br2 C4 C5 C6 176.4(3)
C4 C5 C6 C1 -1.0(6)
C4 C5 C6 C7 -179.6(3)
C2 C1 C6 C5 3.2(5)
N2 C1 C6 C5 -173.7(3)
C2 C1 C6 C7 -178.2(3)
N2 C1 C6 C7 4.9(5)
C8 N1 C7 C6 80.4(4)
C15 N1 C7 C6 -43.1(4)
C5 C6 C7 N1 -172.6(3)
C1 C6 C7 N1 8.8(5)
C15 N1 C8 C9 -157.5(4)
C7 N1 C8 C9 80.5(4)
C15 N1 C8 C13 18.2(5)
C7 N1 C8 C13 -103.7(4)
C13 C8 C9 C10 0.8(6)
N1 C8 C9 C10 176.6(3)
C13 C8 C9 Br3 -175.0(3)
N1 C8 C9 Br3 0.8(5)
C8 C9 C10 C11 -1.8(6)
Br3 C9 C10 C11 174.0(3)
C9 C10 C11 C12 2.3(6)
C9 C10 C11 Br4 -175.8(3)
C10 C11 C12 C13 -1.8(6)
Br4 C11 C12 C13 176.3(3)
C11 C12 C13 C8 0.8(6)
C11 C12 C13 C14 -179.1(3)
C9 C8 C13 C12 -0.2(5)
N1 C8 C13 C12 -176.0(3)
C9 C8 C13 C14 179.6(3)
N1 C8 C13 C14 3.8(5)
C1 N2 C14 C13 79.4(4)
C15 N2 C14 C13 -43.9(4)
C12 C13 C14 N2 -170.2(3)
C8 C13 C14 N2 10.0(5)
C1 N2 C15 N1 -55.6(4)
C14 N2 C15 N1 69.8(4)
C8 N1 C15 N2 -56.1(4)
C7 N1 C15 N2 69.5(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21127472
