#------------------------------------------------------------------------------
#$Date: 2019-11-11 18:07:18 +0200 (Mon, 11 Nov 2019) $
#$Revision: 226843 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/53/4035386.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_4035386
loop_
_publ_author_name
'Wu, Jun'
'Zhang, Hui'
'Ding, Xiao'
'Tan, Xuefei'
'Chen, Jie'
'He, Weimin'
'Deng, Hongmei'
'Song, Liping'
'Shen, Hong C.'
'Cao, Weiguo'
_publ_section_title
;
 Potassium Iodide-Promoted One-Pot Synthesis of Fluoroalkylated
 Quinoxalines via a Tandem Michael Addition/Azidation/Cycloamination
 Approach.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9422
_journal_page_last               9429
_journal_paper_doi               10.1021/acs.joc.8b01030
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C11 H6 Br F3 N2 O2'
_chemical_formula_weight         335.09
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 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                 90.86(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.905(13)
_cell_length_b                   18.25(5)
_cell_length_c                   13.37(3)
_cell_measurement_reflns_used    1730
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.92
_cell_measurement_theta_min      2.70
_cell_volume                     1197(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0557
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5844
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    3.473
_exptl_absorpt_correction_T_max  0.8455
_exptl_absorpt_correction_T_min  0.4654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.860
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2106
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0428
_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)+(0.0474P)²+0.5074P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1113
_reflns_number_gt                1529
_reflns_number_total             2106
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b01030_si_002.cif
_cod_data_source_block           171214a_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4035386
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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
Br1 Br 0.28406(10) 0.27994(2) 0.90477(4) 0.0569(2) Uani 1 1 d .
F1 F 0.9102(11) 0.08104(18) 0.9479(2) 0.1207(17) Uani 1 1 d .
F2 F 0.7904(8) 0.00486(16) 0.8414(3) 0.1010(12) Uani 1 1 d .
F3 F 1.1938(7) 0.03830(19) 0.8469(3) 0.0958(11) Uani 1 1 d .
C1 C 0.4528(9) 0.2827(2) 0.7786(3) 0.0420(10) Uani 1 1 d .
C2 C 0.3923(10) 0.3375(2) 0.7149(4) 0.0556(13) Uani 1 1 d .
H2 H 0.2627 0.3722 0.7325 0.067 Uiso 1 1 calc R
C3 C 0.5211(11) 0.3431(3) 0.6228(4) 0.0628(14) Uani 1 1 d .
H3 H 0.4788 0.3820 0.5805 0.075 Uiso 1 1 calc R
C4 C 0.7074(10) 0.2925(2) 0.5941(4) 0.0558(13) Uani 1 1 d .
H4 H 0.7926 0.2967 0.5327 0.067 Uiso 1 1 calc R
C5 C 0.7698(9) 0.2336(2) 0.6586(3) 0.0435(11) Uani 1 1 d .
C6 C 1.0020(8) 0.1267(2) 0.6884(3) 0.0392(10) Uani 1 1 d .
C7 C 0.8801(8) 0.1227(2) 0.7831(3) 0.0406(10) Uani 1 1 d .
C8 C 0.6433(9) 0.2276(2) 0.7525(3) 0.0393(10) Uani 1 1 d .
C9 C 0.9445(11) 0.0624(2) 0.8563(4) 0.0551(12) Uani 1 1 d .
C10 C 1.1955(9) 0.0709(2) 0.6466(3) 0.0439(11) Uani 1 1 d .
C11 C 1.2430(11) -0.0516(3) 0.5975(4) 0.0705(16) Uani 1 1 d .
H11A H 1.2900 -0.0401 0.5298 0.106 Uiso 1 1 calc R
H11B H 1.1443 -0.0970 0.5987 0.106 Uiso 1 1 calc R
H11C H 1.4064 -0.0561 0.6375 0.106 Uiso 1 1 calc R
N1 N 0.9533(7) 0.18195(19) 0.6275(3) 0.0456(9) Uani 1 1 d .
N2 N 0.7036(7) 0.17149(17) 0.8153(3) 0.0409(9) Uani 1 1 d .
O1 O 1.4215(7) 0.08347(19) 0.6220(3) 0.0748(11) Uani 1 1 d .
O2 O 1.0744(6) 0.00637(15) 0.6374(3) 0.0570(9) Uani 1 1 d .
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'
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
C2 C1 C8 120.7(5)
C2 C1 Br1 119.3(4)
C8 C1 Br1 120.0(3)
C1 C2 C3 121.0(5)
C1 C2 H2 119.5
C3 C2 H2 119.5
C4 C3 C2 120.9(4)
C4 C3 H3 119.5
C2 C3 H3 119.5
C3 C4 C5 119.1(5)
C3 C4 H4 120.4
C5 C4 H4 120.4
N1 C5 C4 118.4(5)
N1 C5 C8 121.0(4)
C4 C5 C8 120.6(4)
N1 C6 C7 121.3(4)
N1 C6 C10 113.5(4)
C7 C6 C10 125.2(4)
N2 C7 C6 123.2(4)
N2 C7 C9 114.5(4)
C6 C7 C9 122.3(4)
N2 C8 C5 121.0(4)
N2 C8 C1 121.4(4)
C5 C8 C1 117.6(4)
F1 C9 F2 105.9(5)
F1 C9 F3 108.4(4)
F2 C9 F3 104.7(4)
F1 C9 C7 113.4(4)
F2 C9 C7 112.0(4)
F3 C9 C7 111.8(4)
O1 C10 O2 124.6(4)
O1 C10 C6 124.7(4)
O2 C10 C6 110.6(4)
O2 C11 H11A 109.5
O2 C11 H11B 109.5
H11A C11 H11B 109.5
O2 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C6 N1 C5 116.9(4)
C7 N2 C8 116.5(4)
C10 O2 C11 115.2(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.890(6)
F1 C9 1.285(7)
F2 C9 1.307(6)
F3 C9 1.307(6)
C1 C2 1.344(6)
C1 C8 1.420(6)
C2 C3 1.397(8)
C2 H2 0.9300
C3 C4 1.358(7)
C3 H3 0.9300
C4 C5 1.409(6)
C4 H4 0.9300
C5 N1 1.372(6)
C5 C8 1.412(7)
C6 N1 1.316(6)
C6 C7 1.410(7)
C6 C10 1.506(6)
C7 N2 1.319(5)
C7 C9 1.503(7)
C8 N2 1.355(6)
C10 O1 1.184(6)
C10 O2 1.323(6)
C11 O2 1.450(6)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
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
C8 C1 C2 C3 -2.1(7)
Br1 C1 C2 C3 177.3(4)
C1 C2 C3 C4 1.3(8)
C2 C3 C4 C5 0.1(7)
C3 C4 C5 N1 178.4(4)
C3 C4 C5 C8 -0.8(7)
N1 C6 C7 N2 2.8(6)
C10 C6 C7 N2 -177.4(4)
N1 C6 C7 C9 -176.5(4)
C10 C6 C7 C9 3.4(6)
N1 C5 C8 N2 1.4(6)
C4 C5 C8 N2 -179.5(4)
N1 C5 C8 C1 -179.1(4)
C4 C5 C8 C1 0.1(6)
C2 C1 C8 N2 -179.1(4)
Br1 C1 C8 N2 1.5(5)
C2 C1 C8 C5 1.4(6)
Br1 C1 C8 C5 -178.0(3)
N2 C7 C9 F1 -26.0(6)
C6 C7 C9 F1 153.3(5)
N2 C7 C9 F2 93.8(5)
C6 C7 C9 F2 -86.8(6)
N2 C7 C9 F3 -149.0(4)
C6 C7 C9 F3 30.4(6)
N1 C6 C10 O1 59.2(6)
C7 C6 C10 O1 -120.7(5)
N1 C6 C10 O2 -118.3(4)
C7 C6 C10 O2 61.8(5)
C7 C6 N1 C5 -2.8(6)
C10 C6 N1 C5 177.3(3)
C4 C5 N1 C6 -178.3(4)
C8 C5 N1 C6 0.8(6)
C6 C7 N2 C8 -0.5(6)
C9 C7 N2 C8 178.9(4)
C5 C8 N2 C7 -1.5(6)
C1 C8 N2 C7 179.0(4)
O1 C10 O2 C11 2.5(7)
C6 C10 O2 C11 179.9(4)
