#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/23/1512335.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_1512335
loop_
_publ_author_name
'Wang, Yong'
'Chen, Chao'
'Zhang, Shu'
'Lou, Zhenbang'
'Su, Xiang'
'Wen, Lirong'
'Li, Ming'
_publ_section_title
;
 A Concise Construction of Polycyclic Quinolines via Annulation of
 ω-Cyano-1-alkynes with Diaryliodonium Salts
;
_journal_issue                   18
_journal_name_full               'Organic Letters'
_journal_page_first              4794
_journal_paper_doi               10.1021/ol402164s
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C13 H9 Br F3 N'
_chemical_formula_sum            'C13 H9 Br F3 N'
_chemical_formula_weight         316.12
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_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                 104.56(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.7310(15)
_cell_length_b                   7.195(3)
_cell_length_c                   10.886(4)
_cell_measurement_reflns_used    41
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      12.51
_cell_measurement_theta_min      5.46
_cell_volume                     586.1(3)
_computing_cell_refinement       'XSCANS (Bruker, 1997)'
_computing_data_collection       'XSCANS (Bruker, 1997)'
_computing_data_reduction        'XSCANS (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_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  0.0755
_diffrn_reflns_av_sigmaI/netI    0.0750
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2507
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.93
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.525
_exptl_absorpt_correction_T_max  0.3768
_exptl_absorpt_correction_T_min  0.2287
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SHELXTL (Bruker, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         1184
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0334
_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)+(0.0010P)²+0.3000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0821
_reflns_number_gt                1048
_reflns_number_total             1184
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ol402164s_si_001.cif
_cod_data_source_block           chenc-21
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        586.0(3)
_cod_original_sg_symbol_H-M      P2(1)/m
_cod_database_code               1512335
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
Br1 Br 0.04206(5) 0.2500 0.42134(4) 0.05024(18) Uani 1 2 d S
F1 F 0.1517(4) 0.1047(5) -0.1238(2) 0.1081(11) Uani 1 1 d .
F2 F -0.0337(4) 0.2500 -0.0474(3) 0.114(2) Uani 1 2 d S
N1 N 0.6471(4) 0.2500 0.4151(3) 0.0452(9) Uani 1 2 d S
C1 C 0.2841(5) 0.2500 0.4164(4) 0.0383(9) Uani 1 2 d S
C2 C 0.4134(5) 0.2500 0.5264(4) 0.0402(9) Uani 1 2 d S
C3 C 0.3999(6) 0.2500 0.6609(4) 0.0495(11) Uani 1 2 d S
H3 H 0.3373 0.1403 0.6787 0.059 Uiso 1 1 d R
C4 C 0.5951(6) 0.2500 0.7404(4) 0.0559(12) Uani 1 2 d S
H4 H 0.6176 0.3593 0.7943 0.067 Uiso 1 1 d R
C5 C 0.7179(6) 0.2500 0.6508(4) 0.0491(11) Uani 1 2 d S
H5 H 0.7933 0.3597 0.6637 0.059 Uiso 1 1 d R
C6 C 0.5934(5) 0.2500 0.5194(4) 0.0415(9) Uani 1 2 d S
C7 C 0.5163(5) 0.2500 0.3032(4) 0.0430(10) Uani 1 2 d S
C8 C 0.5688(6) 0.2500 0.1894(4) 0.0551(13) Uani 1 2 d S
H8 H 0.6897 0.2500 0.1914 0.066 Uiso 1 2 calc SR
C9 C 0.4452(6) 0.2500 0.0761(4) 0.0589(14) Uani 1 2 d S
H9 H 0.4820 0.2500 0.0011 0.071 Uiso 1 2 calc SR
C10 C 0.2640(6) 0.2500 0.0717(4) 0.0509(11) Uani 1 2 d S
C11 C 0.2073(5) 0.2500 0.1800(4) 0.0475(11) Uani 1 2 d S
H11 H 0.0855 0.2500 0.1753 0.057 Uiso 1 2 calc SR
C12 C 0.3312(5) 0.2500 0.2998(4) 0.0386(9) Uani 1 2 d S
C13 C 0.1320(8) 0.2500 -0.0545(4) 0.0705(17) Uani 1 2 d S
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'
F F 0.0171 0.0103 '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
C6 N1 C7 116.6(4) . .
C2 C1 C12 119.8(4) . .
C2 C1 Br1 119.5(3) . .
C12 C1 Br1 120.7(3) . .
C1 C2 C6 118.1(4) . .
C1 C2 C3 130.5(4) . .
C6 C2 C3 111.4(4) . .
C2 C3 C4 104.5(4) . .
C2 C3 H3 110.9 . .
C4 C3 H3 110.8 . .
C5 C4 C3 108.7(3) . .
C5 C4 H4 110.0 . .
C3 C4 H4 109.9 . .
C6 C5 C4 104.8(4) . .
C6 C5 H5 110.7 . .
C4 C5 H5 110.8 . .
N1 C6 C2 125.5(4) . .
N1 C6 C5 124.0(4) . .
C2 C6 C5 110.5(4) . .
N1 C7 C8 118.3(4) . .
N1 C7 C12 122.3(4) . .
C8 C7 C12 119.4(4) . .
C9 C8 C7 120.8(4) . .
C9 C8 H8 119.6 . .
C7 C8 H8 119.6 . .
C8 C9 C10 120.3(4) . .
C8 C9 H9 119.9 . .
C10 C9 H9 119.9 . .
C11 C10 C9 120.8(4) . .
C11 C10 C13 120.3(4) . .
C9 C10 C13 118.8(4) . .
C10 C11 C12 120.7(4) . .
C10 C11 H11 119.6 . .
C12 C11 H11 119.6 . .
C1 C12 C11 124.4(4) . .
C1 C12 C7 117.7(3) . .
C11 C12 C7 118.0(4) . .
F2 C13 F1 106.9(3) . .
F2 C13 F1 106.9(3) . 4_565
F1 C13 F1 104.7(4) . 4_565
F2 C13 C10 113.6(4) . .
F1 C13 C10 112.1(3) . .
F1 C13 C10 112.1(3) 4_565 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.885(4) .
F1 C13 1.320(4) .
F2 C13 1.303(7) .
N1 C6 1.303(6) .
N1 C7 1.374(5) .
C1 C2 1.354(5) .
C1 C12 1.405(6) .
C2 C6 1.413(5) .
C2 C3 1.495(6) .
C3 C4 1.539(6) .
C3 H3 0.9700 .
C4 C5 1.523(7) .
C4 H4 0.9700 .
C5 C6 1.510(5) .
C5 H5 0.9700 .
C7 C8 1.396(6) .
C7 C12 1.422(5) .
C8 C9 1.357(6) .
C8 H8 0.9300 .
C9 C10 1.390(6) .
C9 H9 0.9300 .
C10 C11 1.358(6) .
C10 C13 1.491(6) .
C11 C12 1.410(5) .
C11 H11 0.9300 .
C13 F1 1.320(4) 4_565
