#------------------------------------------------------------------------------
#$Date: 2019-11-24 03:17:03 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236451 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/40/1554025.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_1554025
loop_
_publ_author_name
'Sun, Xingxing'
'Zhang, Baicheng'
'Li, Xinyang'
'Trindle, Carl O.'
'Zhang, Guoqing'
_publ_section_title
;
 External Heavy-Atom Effect via Orbital Interactions Revealed by
 Single-Crystal X-ray Diffraction.
;
_journal_issue                   29
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              5791
_journal_page_last               5797
_journal_paper_doi               10.1021/acs.jpca.6b03867
_journal_volume                  120
_journal_year                    2016
_chemical_formula_sum            'C12 H11 F3 I N'
_chemical_formula_weight         353.12
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.8119(12)
_cell_length_b                   7.3074(4)
_cell_length_c                   11.4308(5)
_cell_measurement_reflns_used    1236
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.8254
_cell_measurement_theta_min      3.0648
_cell_volume                     1320.76(14)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4216
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.133
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.438
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.270
_refine_diff_density_max         0.710
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1452
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0371P)²+1.1434P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0870
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1162
_reflns_number_total             1452
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp6b03867_si_010.cif
_cod_data_source_block           shelxl
_cod_database_code               1554025
_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   0.474
_shelx_estimated_absorpt_t_max   0.559
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
F1 F 0.4025(4) 0.7500 0.7897(5) 0.205(4) Uani 1 2 d S T P
F2 F 0.4880(3) 0.6101(6) 0.8843(4) 0.1699(19) Uani 1 1 d . . .
N1 N 0.7085(3) 0.7500 0.4378(4) 0.0504(10) Uani 1 2 d S T P
C1 C 0.6797(4) 0.7500 0.3295(5) 0.0629(14) Uani 1 2 d S T P
H1 H 0.7179 0.7500 0.2676 0.075 Uiso 1 2 calc R U P
C2 C 0.5942(4) 0.7500 0.3059(6) 0.0778(18) Uani 1 2 d S T P
H2 H 0.5756 0.7500 0.2287 0.093 Uiso 1 2 calc R U P
C3 C 0.5369(4) 0.7500 0.3942(6) 0.0733(17) Uani 1 2 d S T P
H3 H 0.4792 0.7500 0.3782 0.088 Uiso 1 2 calc R U P
C4 C 0.5662(4) 0.7500 0.5102(5) 0.0568(14) Uani 1 2 d S T P
C5 C 0.5101(4) 0.7500 0.6073(5) 0.0677(16) Uani 1 2 d S T P
H5 H 0.4520 0.7500 0.5942 0.081 Uiso 1 2 calc R U P
C6 C 0.5392(4) 0.7500 0.7176(5) 0.0632(15) Uani 1 2 d S T P
C7 C 0.6277(4) 0.7500 0.7380(5) 0.0652(15) Uani 1 2 d S T P
H7 H 0.6476 0.7500 0.8145 0.078 Uiso 1 2 calc R U P
C8 C 0.6837(4) 0.7500 0.6482(5) 0.0594(14) Uani 1 2 d S T P
H8 H 0.7416 0.7500 0.6631 0.071 Uiso 1 2 calc R U P
C9 C 0.6539(3) 0.7500 0.5325(4) 0.0491(12) Uani 1 2 d S T P
C10 C 0.4823(5) 0.7500 0.8200(7) 0.089(2) Uani 1 2 d S T P
C11 C 0.8016(4) 0.7500 0.4618(5) 0.0600(14) Uani 1 2 d S T P
H11A H 0.8150 0.8570 0.5084 0.072 Uiso 0.5 1 calc R U P
H11B H 0.8150 0.6430 0.5084 0.072 Uiso 0.5 1 calc R U P
C12 C 0.8570(4) 0.7500 0.3557(6) 0.084(2) Uani 1 2 d S T P
H12A H 0.9152 0.7500 0.3795 0.126 Uiso 1 2 d S U P
H12C H 0.8456 0.6427 0.3099 0.126 Uiso 1 1 d . U .
I1 I 0.77455(3) 0.7500 0.01750(3) 0.06572(19) Uani 1 2 d S T P
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
H H 0.0000 0.0000 '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
C1 N1 C9 121.2(5) .
C1 N1 C11 120.8(5) .
C9 N1 C11 118.0(4) .
N1 C1 C2 121.6(6) .
N1 C1 H1 119.2 .
C2 C1 H1 119.2 .
C3 C2 C1 120.6(6) .
C3 C2 H2 119.7 .
C1 C2 H2 119.7 .
C2 C3 C4 118.8(6) .
C2 C3 H3 120.6 .
C4 C3 H3 120.6 .
C3 C4 C9 119.7(5) .
C3 C4 C5 122.1(6) .
C9 C4 C5 118.2(5) .
C6 C5 C4 121.3(6) .
C6 C5 H5 119.4 .
C4 C5 H5 119.4 .
C5 C6 C7 119.5(6) .
C5 C6 C10 122.4(6) .
C7 C6 C10 118.1(6) .
C8 C7 C6 121.3(5) .
C8 C7 H7 119.3 .
C6 C7 H7 119.3 .
C7 C8 C9 119.6(5) .
C7 C8 H8 120.2 .
C9 C8 H8 120.2 .
N1 C9 C8 121.8(5) .
N1 C9 C4 118.2(5) .
C8 C9 C4 120.0(5) .
F2 C10 F2 108.2(7) 8_575
F2 C10 F1 102.9(5) 8_575
F2 C10 F1 102.9(5) .
F2 C10 C6 114.7(4) 8_575
F2 C10 C6 114.7(4) .
F1 C10 C6 112.2(7) .
C12 C11 N1 115.3(5) .
C12 C11 H11A 108.5 .
N1 C11 H11A 108.5 .
C12 C11 H11B 108.5 .
N1 C11 H11B 108.5 .
H11A C11 H11B 107.5 .
C11 C12 H12A 109.4(6) .
C11 C12 H12C 109.4(4) .
H12A C12 H12C 109.5(5) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C10 1.308(9) .
F2 C10 1.262(5) .
N1 C1 1.320(7) .
N1 C9 1.385(7) .
N1 C11 1.496(7) .
C1 C2 1.378(8) .
C1 H1 0.9300 .
C2 C3 1.357(9) .
C2 H2 0.9300 .
C3 C4 1.405(8) .
C3 H3 0.9300 .
C4 C9 1.411(8) .
C4 C5 1.421(8) .
C5 C6 1.342(8) .
C5 H5 0.9300 .
C6 C7 1.418(8) .
C6 C10 1.477(9) .
C7 C8 1.357(8) .
C7 H7 0.9300 .
C8 C9 1.403(7) .
C8 H8 0.9300 .
C10 F2 1.262(5) 8_575
C11 C12 1.496(8) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 H12A 0.960(7) .
C12 H12C 0.959(4) .
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
_geom_torsion_site_symmetry_4
C9 N1 C1 C2 0.000(1) .
C11 N1 C1 C2 180.000(1) .
N1 C1 C2 C3 0.000(1) .
C1 C2 C3 C4 0.000(1) .
C2 C3 C4 C9 0.000(1) .
C2 C3 C4 C5 180.000(1) .
C3 C4 C5 C6 180.000(1) .
C9 C4 C5 C6 0.000(1) .
C4 C5 C6 C7 0.000(1) .
C4 C5 C6 C10 180.000(1) .
C5 C6 C7 C8 0.000(1) .
C10 C6 C7 C8 180.000(1) .
C6 C7 C8 C9 0.000(1) .
C1 N1 C9 C8 180.000(1) .
C11 N1 C9 C8 0.000(1) .
C1 N1 C9 C4 0.000(1) .
C11 N1 C9 C4 180.000(1) .
C7 C8 C9 N1 180.000(1) .
C7 C8 C9 C4 0.000(1) .
C3 C4 C9 N1 0.000(1) .
C5 C4 C9 N1 180.000(1) .
C3 C4 C9 C8 180.000(1) .
C5 C4 C9 C8 0.000(1) .
C5 C6 C10 F2 -116.9(6) 8_575
C7 C6 C10 F2 63.1(6) 8_575
C5 C6 C10 F2 116.9(6) .
C7 C6 C10 F2 -63.1(6) .
C5 C6 C10 F1 0.000(2) .
C7 C6 C10 F1 180.000(1) .
C1 N1 C11 C12 0.000(1) .
C9 N1 C11 C12 180.000(1) .
