#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:28:02 +0100 (lun 21 de mar de 2016) $
#$Revision: 178470 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/91/4029185.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_4029185
loop_
_publ_author_name
'Lin, Mei-Huey'
'Huang, Yen-Chih'
'Kuo, Chung-Kai'
'Tsai, Chang-Hsien'
'Li, Yi-Syuan'
'Hu, Ting-Chia'
'Chuang, Tsung-Hsun'
_publ_section_title
;
 γ-Halo-enones: A Method for their Synthesis from Arylacyl Halides and
 Their Application to the Preparation of Five-Membered Ring Heterocycles.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2751
_journal_page_last               2757
_journal_paper_doi               10.1021/jo5001274
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C12 H10 Br N O'
_chemical_formula_weight         264.12
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.574(12)
_cell_angle_beta                 100.912(12)
_cell_angle_gamma                112.227(11)
_cell_formula_units_Z            2
_cell_length_a                   8.3861(14)
_cell_length_b                   8.3872(14)
_cell_length_c                   9.0080(16)
_cell_measurement_reflns_used    2397
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      24.377
_cell_measurement_theta_min      2.344
_cell_volume                     565.89(18)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      250(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       /w
_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  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7697
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    3.604
_exptl_absorpt_correction_T_max  0.4912
_exptl_absorpt_correction_T_min  0.4319
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2793
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0341
_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)+(0.0382P)²+0.1997P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0846
_reflns_number_gt                2095
_reflns_number_total             2793
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5001274_si_002.cif
_cod_data_source_block           hyj1380201
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/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_cell_volume        565.89(17)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4029185
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 0.58452(4) 0.75665(4) 0.83209(3) 0.05583(13) Uani 1 1 d .
O1 O 0.3245(3) 0.8696(2) 0.3890(2) 0.0548(5) Uani 1 1 d .
N1 N 0.0468(3) -0.1840(3) 0.8519(3) 0.0497(6) Uani 1 1 d .
C12 C 0.3079(5) 0.6798(4) 0.1689(3) 0.0590(8) Uani 1 1 d .
H1A H 0.3317 0.7827 0.1235 0.089 Uiso 1 1 calc R
H1B H 0.1960 0.5896 0.1119 0.089 Uiso 1 1 calc R
H1C H 0.4006 0.6395 0.1667 0.089 Uiso 1 1 calc R
C11 C 0.3006(3) 0.7228(3) 0.3325(3) 0.0408(6) Uani 1 1 d .
C10 C 0.2577(3) 0.5742(3) 0.4166(3) 0.0397(5) Uani 1 1 d .
H3 H 0.2009 0.4626 0.3562 0.048 Uiso 1 1 calc R
C8 C 0.2911(3) 0.5819(3) 0.5692(3) 0.0336(5) Uani 1 1 d .
C5 C 0.2371(3) 0.4168(3) 0.6317(3) 0.0332(5) Uani 1 1 d .
C4 C 0.2528(3) 0.2689(3) 0.5609(3) 0.0382(5) Uani 1 1 d .
H6 H 0.2983 0.2745 0.4741 0.046 Uiso 1 1 calc R
C3 C 0.2019(3) 0.1155(3) 0.6176(3) 0.0387(5) Uani 1 1 d .
H7 H 0.2129 0.0185 0.5691 0.046 Uiso 1 1 calc R
C2 C 0.1342(3) 0.1056(3) 0.7473(3) 0.0358(5) Uani 1 1 d .
C1 C 0.0837(3) -0.0549(3) 0.8068(3) 0.0396(6) Uani 1 1 d .
C6 C 0.1689(3) 0.4040(3) 0.7623(3) 0.0399(6) Uani 1 1 d .
H10 H 0.1582 0.5008 0.8115 0.048 Uiso 1 1 calc R
C7 C 0.1171(3) 0.2506(3) 0.8194(3) 0.0403(6) Uani 1 1 d .
H11 H 0.0710 0.2441 0.9058 0.048 Uiso 1 1 calc R
C9 C 0.3805(3) 0.7515(3) 0.6828(3) 0.0402(6) Uani 1 1 d .
H12A H 0.2959 0.7669 0.7365 0.048 Uiso 1 1 calc R
H12B H 0.4193 0.8479 0.6282 0.048 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 0.05131(18) 0.0595(2) 0.04489(18) 0.00156(13) -0.00387(12) 0.01913(14)
O1 0.0775(14) 0.0417(11) 0.0456(11) 0.0113(9) 0.0142(10) 0.0244(10)
N1 0.0577(14) 0.0462(13) 0.0486(13) 0.0148(11) 0.0199(11) 0.0200(11)
C12 0.084(2) 0.0627(19) 0.0415(16) 0.0186(14) 0.0222(15) 0.0358(17)
C11 0.0416(13) 0.0438(14) 0.0367(14) 0.0103(11) 0.0074(11) 0.0172(11)
C10 0.0430(13) 0.0338(12) 0.0372(13) 0.0076(10) 0.0072(11) 0.0111(11)
C8 0.0328(11) 0.0358(12) 0.0339(12) 0.0065(10) 0.0095(10) 0.0149(10)
C5 0.0305(11) 0.0370(12) 0.0306(12) 0.0062(9) 0.0063(9) 0.0129(10)
C4 0.0441(13) 0.0428(14) 0.0326(12) 0.0086(10) 0.0163(11) 0.0193(11)
C3 0.0455(13) 0.0365(13) 0.0378(13) 0.0069(10) 0.0123(11) 0.0198(11)
C2 0.0337(12) 0.0396(13) 0.0344(12) 0.0101(10) 0.0087(10) 0.0143(10)
C1 0.0379(13) 0.0439(15) 0.0388(14) 0.0090(11) 0.0124(11) 0.0170(11)
C6 0.0477(14) 0.0419(14) 0.0363(13) 0.0060(11) 0.0153(11) 0.0227(12)
C7 0.0451(14) 0.0489(15) 0.0349(13) 0.0129(11) 0.0187(11) 0.0223(12)
C9 0.0458(14) 0.0392(13) 0.0372(13) 0.0069(10) 0.0090(11) 0.0196(11)
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
C11 C12 H1A 109.5
C11 C12 H1B 109.5
H1A C12 H1B 109.5
C11 C12 H1C 109.5
H1A C12 H1C 109.5
H1B C12 H1C 109.5
O1 C11 C10 123.1(2)
O1 C11 C12 121.1(2)
C10 C11 C12 115.8(2)
C8 C10 C11 127.7(2)
C8 C10 H3 116.2
C11 C10 H3 116.2
C10 C8 C5 119.6(2)
C10 C8 C9 122.9(2)
C5 C8 C9 117.4(2)
C6 C5 C4 117.9(2)
C6 C5 C8 121.2(2)
C4 C5 C8 120.8(2)
C3 C4 C5 121.1(2)
C3 C4 H6 119.5
C5 C4 H6 119.5
C4 C3 C2 120.0(2)
C4 C3 H7 120.0
C2 C3 H7 120.0
C3 C2 C7 119.9(2)
C3 C2 C1 119.5(2)
C7 C2 C1 120.6(2)
N1 C1 C2 178.0(3)
C7 C6 C5 121.3(2)
C7 C6 H10 119.4
C5 C6 H10 119.4
C6 C7 C2 119.7(2)
C6 C7 H11 120.1
C2 C7 H11 120.1
C8 C9 Br1 111.56(16)
C8 C9 H12A 109.3
Br1 C9 H12A 109.3
C8 C9 H12B 109.3
Br1 C9 H12B 109.3
H12A C9 H12B 108.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C9 1.949(2)
O1 C11 1.212(3)
N1 C1 1.146(3)
C12 C11 1.501(4)
C12 H1A 0.9600
C12 H1B 0.9600
C12 H1C 0.9600
C11 C10 1.484(4)
C10 C8 1.340(3)
C10 H3 0.9300
C8 C5 1.487(3)
C8 C9 1.501(3)
C5 C6 1.398(3)
C5 C4 1.402(3)
C4 C3 1.376(3)
C4 H6 0.9300
C3 C2 1.389(3)
C3 H7 0.9300
C2 C7 1.391(3)
C2 C1 1.440(4)
C6 C7 1.377(3)
C6 H10 0.9300
C7 H11 0.9300
C9 H12A 0.9700
C9 H12B 0.9700
