#------------------------------------------------------------------------------
#$Date: 2017-07-27 03:37:32 +0300 (Thu, 27 Jul 2017) $
#$Revision: 199348 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/67/1546735.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_1546735
loop_
_publ_author_name
'Zhu, Haoxuan'
'Janusson, Eric'
'Luo, Jingwei'
'Piers, James'
'Islam, Farhana'
'McGarvey, Bryce'
'Oliver, Allen Grayson'
'Granot, Ori'
'McIndoe, Jason Scott'
_publ_section_title
;
 Phenol-selective mass spectrometric analysis of jet fuel
;
_journal_name_full               'The Analyst'
_journal_paper_doi               10.1039/C7AN00908A
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H14 Br N2, F6 P'
_chemical_formula_sum            'C12 H14 Br F6 N2 P'
_chemical_formula_weight         411.13
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     vecmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-07-19 deposited with the CCDC.
2017-07-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3093(6)
_cell_length_b                   10.6750(8)
_cell_length_c                   16.8309(13)
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.26
_cell_volume                     1492.93(19)
_computing_cell_refinement       'Bruker SAINT v8.34A'
_computing_data_collection       'Bruker APEX-II v2014-5.0'
_computing_data_reduction        'Bruker SAINT v8.34A'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa X8-APEX-II'
_diffrn_measurement_method       'combination of ω and φ-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  0.0348
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            26499
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.493
_diffrn_reflns_theta_min         2.259
_exptl_absorpt_coefficient_mu    2.922
_exptl_absorpt_correction_T_max  0.9363
_exptl_absorpt_correction_T_min  0.7187
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.829
_exptl_crystal_description       tablet
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1404 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3765
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0221
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0242P)²+0.1276P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0505
_refine_ls_wR_factor_ref         0.0516
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3516
_reflns_number_total             3765
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7an00908a2.cif
_cod_data_source_block           uvic1410
_cod_database_code               1546735
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.593
_shelx_estimated_absorpt_t_max   0.844
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Br1 Br -0.18657(3) 0.60389(3) 0.43860(2) 0.02557(8) Uani 1 1 d . .
N1 N 0.5857(3) 0.2976(2) 0.57922(12) 0.0171(4) Uani 1 1 d . .
N2 N 0.6362(3) 0.2148(2) 0.69274(13) 0.0198(5) Uani 1 1 d . .
C1 C 0.5663(3) 0.1959(2) 0.62354(16) 0.0194(5) Uani 1 1 d . .
H1A H 0.5113 0.1219 0.6079 0.023 Uiso 1 1 calc R U
C2 C 0.6706(3) 0.3844(2) 0.62240(16) 0.0241(6) Uani 1 1 d . .
H2A H 0.7014 0.4658 0.6054 0.029 Uiso 1 1 calc R U
C3 C 0.7020(4) 0.3319(3) 0.69358(16) 0.0260(6) Uani 1 1 d . .
H3A H 0.7591 0.3694 0.7363 0.031 Uiso 1 1 calc R U
C4 C 0.5201(3) 0.3184(3) 0.49966(15) 0.0204(5) Uani 1 1 d . .
H4A H 0.4784 0.2382 0.4785 0.024 Uiso 1 1 calc R U
H4B H 0.6073 0.3473 0.4640 0.024 Uiso 1 1 calc R U
C5 C 0.3869(3) 0.4139(2) 0.49992(14) 0.0151(5) Uani 1 1 d . .
C6 C 0.3694(3) 0.4941(2) 0.43569(15) 0.0169(5) Uani 1 1 d . .
H6A H 0.4436 0.4906 0.3928 0.020 Uiso 1 1 calc R U
C7 C 0.2439(3) 0.5791(2) 0.43408(15) 0.0181(5) Uani 1 1 d . .
H7A H 0.2325 0.6336 0.3898 0.022 Uiso 1 1 calc R U
C8 C 0.1345(3) 0.5859(2) 0.49608(14) 0.0153(5) Uani 1 1 d . .
C9 C 0.1523(3) 0.5057(2) 0.56048(15) 0.0185(5) Uani 1 1 d . .
H9A H 0.0780 0.5093 0.6034 0.022 Uiso 1 1 calc R U
C10 C 0.2777(3) 0.4208(2) 0.56229(15) 0.0176(5) Uani 1 1 d . .
H10A H 0.2894 0.3666 0.6067 0.021 Uiso 1 1 calc R U
C11 C -0.0002(3) 0.6777(3) 0.49382(16) 0.0215(6) Uani 1 1 d . .
H11A H 0.0348 0.7545 0.4658 0.026 Uiso 1 1 calc R U
H11B H -0.0310 0.7011 0.5487 0.026 Uiso 1 1 calc R U
C12 C 0.6420(4) 0.1238(3) 0.75815(18) 0.0335(7) Uani 1 1 d . .
H12A H 0.5720 0.0526 0.7457 0.050 Uiso 1 1 calc R U
H12B H 0.6052 0.1639 0.8073 0.050 Uiso 1 1 calc R U
H12C H 0.7528 0.0943 0.7651 0.050 Uiso 1 1 calc R U
P1 P 0.13988(8) 0.19007(6) 0.75326(4) 0.01773(14) Uani 1 1 d . .
F1 F 0.0167(2) 0.26263(17) 0.80875(10) 0.0305(4) Uani 1 1 d . .
F2 F 0.2477(2) 0.31241(15) 0.74599(10) 0.0362(4) Uani 1 1 d . .
F3 F 0.0354(2) 0.06624(16) 0.76073(11) 0.0373(5) Uani 1 1 d . .
F4 F 0.2403(2) 0.14986(15) 0.83029(10) 0.0311(4) Uani 1 1 d . .
F5 F 0.0405(2) 0.23068(18) 0.67689(9) 0.0365(4) Uani 1 1 d . .
F6 F 0.2634(2) 0.11642(19) 0.69785(11) 0.0409(5) 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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
C1 N1 C2 108.5(2)
C1 N1 C4 126.4(2)
C2 N1 C4 125.0(2)
C1 N2 C3 109.0(2)
C1 N2 C12 125.2(2)
C3 N2 C12 125.8(2)
N2 C1 N1 108.6(2)
C3 C2 N1 106.8(2)
C2 C3 N2 107.1(2)
N1 C4 C5 112.0(2)
C6 C5 C10 119.2(2)
C6 C5 C4 119.5(2)
C10 C5 C4 121.2(2)
C7 C6 C5 120.0(2)
C6 C7 C8 121.0(2)
C7 C8 C9 119.0(2)
C7 C8 C11 120.6(2)
C9 C8 C11 120.4(2)
C10 C9 C8 120.1(2)
C9 C10 C5 120.7(2)
C8 C11 Br1 109.88(17)
F3 P1 F1 90.42(10)
F3 P1 F5 90.40(11)
F1 P1 F5 90.45(10)
F3 P1 F2 178.82(11)
F1 P1 F2 90.45(10)
F5 P1 F2 90.38(10)
F3 P1 F6 89.28(10)
F1 P1 F6 179.64(12)
F5 P1 F6 89.76(11)
F2 P1 F6 89.84(10)
F3 P1 F4 89.87(10)
F1 P1 F4 89.45(9)
F5 P1 F4 179.71(11)
F2 P1 F4 89.35(10)
F6 P1 F4 90.35(10)
N2 C1 H1A 125.7
N1 C1 H1A 125.7
C3 C2 H2A 126.6
N1 C2 H2A 126.6
C2 C3 H3A 126.4
N2 C3 H3A 126.4
N1 C4 H4A 109.2
C5 C4 H4A 109.2
N1 C4 H4B 109.2
C5 C4 H4B 109.2
H4A C4 H4B 107.9
C7 C6 H6A 120.0
C5 C6 H6A 120.0
C6 C7 H7A 119.5
C8 C7 H7A 119.5
C10 C9 H9A 120.0
C8 C9 H9A 120.0
C9 C10 H10A 119.6
C5 C10 H10A 119.6
C8 C11 H11A 109.7
Br1 C11 H11A 109.7
C8 C11 H11B 109.7
Br1 C11 H11B 109.7
H11A C11 H11B 108.2
N2 C12 H12A 109.5
N2 C12 H12B 109.5
H12A C12 H12B 109.5
N2 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C11 1.971(3)
N1 C1 1.327(3)
N1 C2 1.373(3)
N1 C4 1.462(3)
N2 C1 1.317(3)
N2 C3 1.364(4)
N2 C12 1.469(3)
C2 C3 1.348(4)
C4 C5 1.505(4)
C5 C6 1.387(3)
C5 C10 1.389(3)
C6 C7 1.382(4)
C7 C8 1.386(4)
C8 C9 1.389(3)
C8 C11 1.488(3)
C9 C10 1.382(3)
P1 F3 1.5863(18)
P1 F1 1.5873(17)
P1 F5 1.5882(18)
P1 F2 1.5887(17)
P1 F6 1.5940(18)
P1 F4 1.6004(18)
C1 H1A 0.9500
C2 H2A 0.9500
C3 H3A 0.9500
C4 H4A 0.9900
C4 H4B 0.9900
C6 H6A 0.9500
C7 H7A 0.9500
C9 H9A 0.9500
C10 H10A 0.9500
C11 H11A 0.9900
C11 H11B 0.9900
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
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
C3 N2 C1 N1 0.3(3)
C12 N2 C1 N1 -179.6(2)
C2 N1 C1 N2 -0.3(3)
C4 N1 C1 N2 -176.8(2)
C1 N1 C2 C3 0.2(3)
C4 N1 C2 C3 176.8(3)
N1 C2 C3 N2 0.0(3)
C1 N2 C3 C2 -0.2(3)
C12 N2 C3 C2 179.7(3)
C1 N1 C4 C5 108.9(3)
C2 N1 C4 C5 -67.1(3)
N1 C4 C5 C6 145.1(2)
N1 C4 C5 C10 -36.9(3)
C10 C5 C6 C7 -0.4(4)
C4 C5 C6 C7 177.7(2)
C5 C6 C7 C8 0.2(4)
C6 C7 C8 C9 0.0(4)
C6 C7 C8 C11 -180.0(2)
C7 C8 C9 C10 0.1(4)
C11 C8 C9 C10 -179.9(2)
C8 C9 C10 C5 -0.3(4)
C6 C5 C10 C9 0.5(4)
C4 C5 C10 C9 -177.5(2)
C7 C8 C11 Br1 87.6(3)
C9 C8 C11 Br1 -92.3(2)
