#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:07:05 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180466 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/35/7213515.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_7213515
loop_
_publ_author_name
'Lera, Manuel'
'Blake, Alexander J.'
'Wilson, Claire'
'Mascal, Mark'
_publ_section_title
;
 Azatriquinanes. Part 4.1 The chemistry of azatriquinenamine and its
 bromination productsElectronic supplementary information (ESI) available:
 1H-NMR spectra for all new compounds described in this work. See
 http://www.rsc.org/suppdata/p1/b1/b107707d/
;
_journal_issue                   23
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              3145
_journal_paper_doi               10.1039/b107707d
_journal_year                    2001
_chemical_formula_sum            'C9 H10 Br3 N O'
_chemical_formula_weight         387.91
_chemical_name_systematic        ?
_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
;
geometrically placed, except OH from Fourier synthesis 
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.401(4)
_cell_angle_beta                 79.163(3)
_cell_angle_gamma                66.936(3)
_cell_formula_units_Z            2
_cell_length_a                   7.0950(14)
_cell_length_b                   7.9444(16)
_cell_length_c                   10.663(2)
_cell_measurement_reflns_used    2238
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.4
_cell_measurement_theta_min      2.82
_cell_volume                     536.14(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_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      150(2)
_diffrn_measured_fraction_theta_full 0.931
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       omega
_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  0.0027
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3336
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         28.56
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    11.251
_exptl_absorpt_correction_T_max  0.132
_exptl_absorpt_correction_T_min  0.060
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    2.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.26
_refine_diff_density_max         1.087
_refine_diff_density_min         -1.228
_refine_diff_density_rms         0.221
_refine_ls_extinction_coef       0.017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment
'riding model, except OH refined as rigid body'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0425
_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)+(0.0896P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1151
_reflns_number_gt                2039
_reflns_number_total             2337
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b107707dsup1.cif
_cod_data_source_block           compound_14
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        536.15(18)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7213515
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
Br1 Br 0.31178(8) -0.37679(6) 0.88127(5) 0.02280(19) Uani 1 1 d .
Br2 Br 0.41575(7) -0.29691(6) 0.58122(5) 0.02068(18) Uani 1 1 d .
Br3 Br -0.21839(7) -0.22766(7) 0.93647(5) 0.02196(18) Uani 1 1 d .
N N 0.0098(6) 0.1035(5) 0.6359(4) 0.0139(8) Uani 1 1 d .
O1 O -0.0411(5) -0.1813(4) 0.6348(3) 0.0159(6) Uani 1 1 d .
H1 H -0.0027 -0.1574 0.5557 0.024 Uiso 1 1 calc R
C2 C -0.1388(7) -0.0444(6) 0.8221(4) 0.0172(9) Uani 1 1 d .
C8 C 0.3161(8) -0.0256(6) 0.7423(5) 0.0189(10) Uani 1 1 d .
H8A H 0.4677 -0.0610 0.7265 0.023 Uiso 1 1 calc R
H8B H 0.2661 0.0147 0.8280 0.023 Uiso 1 1 calc R
C3 C -0.2392(8) 0.1354(7) 0.8211(5) 0.0216(10) Uani 1 1 d .
H3A H -0.3503 0.1872 0.8836 0.026 Uiso 1 1 calc R
C9 C 0.2529(7) -0.1819(6) 0.7325(4) 0.0160(9) Uani 1 1 d .
C1 C 0.0187(7) -0.0855(6) 0.7040(4) 0.0140(9) Uani 1 1 d .
C7 C 0.2095(7) 0.1241(6) 0.6352(5) 0.0171(9) Uani 1 1 d .
H7A H 0.2948 0.1040 0.5499 0.020 Uiso 1 1 calc R
C6 C 0.1505(8) 0.3246(6) 0.6554(5) 0.0220(10) Uani 1 1 d .
H6A H 0.2580 0.3370 0.6959 0.026 Uiso 1 1 calc R
H6B H 0.1307 0.4104 0.5722 0.026 Uiso 1 1 calc R
C4 C -0.1564(7) 0.2470(6) 0.7096(5) 0.0185(10) Uani 1 1 d .
H4A H -0.2676 0.3274 0.6538 0.022 Uiso 1 1 calc R
C5 C -0.0518(8) 0.3638(7) 0.7453(5) 0.0241(11) Uani 1 1 d .
H5A H -0.1389 0.4972 0.7308 0.029 Uiso 1 1 calc R
H5B H -0.0251 0.3262 0.8371 0.029 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
Br1 0.0278(3) 0.0169(3) 0.0201(3) 0.00352(19) -0.0068(2) -0.0059(2)
Br2 0.0209(3) 0.0180(3) 0.0211(3) -0.00772(19) 0.00250(19) -0.00483(19)
Br3 0.0273(3) 0.0240(3) 0.0166(3) -0.00138(19) 0.00182(19) -0.0144(2)
N 0.0186(18) 0.0096(17) 0.0136(19) -0.0018(14) -0.0016(15) -0.0055(14)
O1 0.0228(16) 0.0159(15) 0.0113(16) -0.0020(12) -0.0027(13) -0.0094(13)
C2 0.021(2) 0.018(2) 0.013(2) -0.0032(18) 0.0017(17) -0.0086(18)
C8 0.026(2) 0.014(2) 0.019(2) -0.0008(17) -0.0037(19) -0.0102(18)
C3 0.022(2) 0.022(2) 0.019(2) -0.0057(19) 0.0029(19) -0.0075(19)
C9 0.020(2) 0.014(2) 0.013(2) -0.0027(16) -0.0006(17) -0.0060(17)
C1 0.017(2) 0.012(2) 0.012(2) -0.0028(16) -0.0008(16) -0.0040(16)
C7 0.023(2) 0.012(2) 0.019(2) -0.0026(17) -0.0041(18) -0.0090(17)
C6 0.029(2) 0.014(2) 0.027(3) -0.0043(19) -0.006(2) -0.0095(19)
C4 0.024(2) 0.011(2) 0.018(2) -0.0053(18) -0.0031(19) -0.0023(18)
C5 0.032(3) 0.017(2) 0.027(3) -0.007(2) -0.004(2) -0.010(2)
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'
O O 0.0106 0.0060 '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
C7 N C1 110.1(3)
C7 N C4 107.9(3)
C1 N C4 108.5(3)
C3 C2 C1 112.2(4)
C3 C2 Br3 123.7(4)
C1 C2 Br3 123.0(3)
C9 C8 C7 101.7(4)
C2 C3 C4 111.6(4)
C8 C9 C1 105.1(4)
C8 C9 Br1 112.2(3)
C1 C9 Br1 116.6(3)
C8 C9 Br2 108.8(3)
C1 C9 Br2 107.8(3)
Br1 C9 Br2 106.2(2)
O1 C1 N 114.6(4)
O1 C1 C2 107.5(4)
N C1 C2 103.2(3)
O1 C1 C9 114.0(3)
N C1 C9 101.8(3)
C2 C1 C9 115.4(4)
N C7 C8 105.4(4)
N C7 C6 104.9(4)
C8 C7 C6 115.8(4)
C5 C6 C7 104.1(4)
C3 C4 N 104.2(4)
C3 C4 C5 115.5(4)
N C4 C5 106.6(4)
C6 C5 C4 104.5(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C9 1.939(5)
Br2 C9 1.971(5)
Br3 C2 1.881(4)
N C7 1.488(6)
N C1 1.501(5)
N C4 1.515(6)
O1 C1 1.386(5)
C2 C3 1.322(7)
C2 C1 1.519(6)
C8 C9 1.505(6)
C8 C7 1.523(6)
C3 C4 1.494(7)
C9 C1 1.591(6)
C7 C6 1.533(6)
C6 C5 1.530(7)
C4 C5 1.535(7)
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
O1 H1 N 0.84 2.00 2.801(5) 159.4 2_556
