#------------------------------------------------------------------------------
#$Date: 2019-11-24 03:35:40 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236520 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/40/1554063.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_1554063
loop_
_publ_author_name
'Xu, Yijue'
'Viger-Gravel, Jasmine'
'Korobkov, Ilia'
'Bryce, David L.'
_publ_section_title
;
 Mechanochemical Production of Halogen-Bonded Solids Featuring
 P═O···I--C Motifs and Characterization via
 X-ray Diffraction, Solid-State Multinuclear Magnetic Resonance, and
 Density Functional Theory
;
_journal_issue                   48
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_page_first              27104
_journal_paper_doi               10.1021/acs.jpcc.5b09737
_journal_volume                  119
_journal_year                    2015
_chemical_formula_sum            'C21 H16 F4 I2 N O P'
_chemical_formula_weight         659.12
_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   geom
_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                   21.9816(16)
_cell_length_b                   18.0739(14)
_cell_length_c                   5.8075(4)
_cell_measurement_reflns_used    9406
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.25
_cell_volume                     2307.3(3)
_computing_cell_refinement       'APEX II, Bruker (2012)'
_computing_data_collection       'APEX II, Bruker (2012)'
_computing_data_reduction        'XPREP, Bruker (2012)'
_computing_molecular_graphics    'SHELXTL, Bruker (2015)'
_computing_publication_material  'SHELXTL, Bruker (2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0098
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            24781
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.300
_diffrn_reflns_theta_min         2.169
_exptl_absorpt_coefficient_mu    2.840
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.897
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.318
_refine_diff_density_min         -1.016
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2874
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0192
_refine_ls_R_factor_gt           0.0182
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0306P)²+1.4838P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0492
_refine_ls_wR_factor_ref         0.0497
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2777
_reflns_number_total             2874
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp5b09737_si_004.cif
_cod_data_source_block           db137a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'n/a' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               1554063
_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   0.428
_shelx_estimated_absorpt_t_max   0.561
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
I1 I 0.10195(2) 0.13817(2) 0.67361(2) 0.02534(5) Uani 1 1 d . . .
O1 O 0.18057(8) 0.2500 0.8487(3) 0.0274(4) Uani 1 2 d S T P
P2 P 0.24826(3) 0.2500 0.88165(10) 0.01816(11) Uani 1 2 d S T P
F1 F -0.01971(5) 0.07223(6) 0.90251(19) 0.0354(2) Uani 1 1 d . . .
F2 F -0.09603(5) -0.03358(8) 0.7727(2) 0.0385(3) Uani 1 1 d . . .
N1 N -0.05281(14) 0.2500 0.7708(7) 0.0606(8) Uani 1 2 d S T P
C1 C 0.04062(7) 0.05663(8) 0.5682(3) 0.0225(3) Uani 1 1 d . . .
C2 C -0.00912(8) 0.03743(9) 0.7014(3) 0.0242(3) Uani 1 1 d . . .
C3 C -0.04855(7) -0.01820(10) 0.6346(3) 0.0248(3) Uani 1 1 d . . .
C4 C 0.27314(7) 0.17048(8) 1.0448(3) 0.0194(3) Uani 1 1 d . . .
C5 C 0.33471(8) 0.15300(10) 1.0660(3) 0.0290(4) Uani 1 1 d . . .
H5A H 0.3644 0.1806 0.9839 0.035 Uiso 1 1 calc R U .
C6 C 0.35240(9) 0.09469(12) 1.2083(3) 0.0363(4) Uani 1 1 d . . .
H6A H 0.3944 0.0834 1.2255 0.044 Uiso 1 1 calc R U .
C7 C 0.30968(10) 0.05344(11) 1.3238(3) 0.0355(4) Uani 1 1 d . . .
H7A H 0.3222 0.0137 1.4200 0.043 Uiso 1 1 calc R U .
C8 C 0.24828(10) 0.06963(10) 1.3002(3) 0.0326(4) Uani 1 1 d . . .
H8A H 0.2187 0.0406 1.3783 0.039 Uiso 1 1 calc R U .
C9 C 0.23008(9) 0.12841(9) 1.1622(3) 0.0250(3) Uani 1 1 d . . .
H9A H 0.1881 0.1399 1.1479 0.030 Uiso 1 1 calc R U .
C10 C 0.29058(14) 0.2500 0.6186(4) 0.0316(5) Uani 1 2 d S T P
H10A H 0.2799 0.2061 0.5281 0.047 Uiso 0.5 1 calc R U P
H10B H 0.3342 0.2492 0.6533 0.047 Uiso 1 2 calc R U P
H10C H 0.2808 0.2946 0.5303 0.047 Uiso 0.5 1 calc R U P
C11 C -0.02859(14) 0.2500 0.9427(6) 0.0449(7) Uani 1 2 d S T P
C12 C 0.0034(2) 0.2500 1.1598(7) 0.0734(13) Uani 1 2 d S T P
H12A H 0.0416 0.2225 1.1435 0.110 Uiso 0.5 1 calc R U P
H12B H -0.0219 0.2264 1.2777 0.110 Uiso 0.5 1 calc R U P
H12C H 0.0123 0.3011 1.2055 0.110 Uiso 0.5 1 calc R U 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'
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'
P P 0.1023 0.0942 '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'
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
O1 P2 C10 114.02(12) . .
O1 P2 C4 111.54(7) . .
C10 P2 C4 106.89(7) . .
O1 P2 C4 111.54(7) . 7_565
C10 P2 C4 106.89(7) . 7_565
C4 P2 C4 105.44(10) . 7_565
C3 C1 C2 116.83(14) 5_556 .
C3 C1 I1 121.62(12) 5_556 .
C2 C1 I1 121.53(12) . .
F1 C2 C3 118.34(15) . .
F1 C2 C1 120.29(15) . .
C3 C2 C1 121.36(15) . .
F2 C3 C1 120.22(15) . 5_556
F2 C3 C2 117.97(15) . .
C1 C3 C2 121.80(15) 5_556 .
C9 C4 C5 119.51(15) . .
C9 C4 P2 119.04(12) . .
C5 C4 P2 121.34(12) . .
C6 C5 C4 119.59(17) . .
C7 C6 C5 120.59(18) . .
C6 C7 C8 120.14(17) . .
C7 C8 C9 119.87(18) . .
C8 C9 C4 120.28(17) . .
N1 C11 C12 178.9(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C1 2.0891(15) .
O1 P2 1.5002(18) .
P2 C10 1.789(3) .
P2 C4 1.8064(15) .
P2 C4 1.8064(15) 7_565
F1 C2 1.3467(19) .
F2 C3 1.3453(19) .
N1 C11 1.131(5) .
C1 C3 1.378(2) 5_556
C1 C2 1.384(2) .
C2 C3 1.383(2) .
C3 C1 1.378(2) 5_556
C4 C9 1.392(2) .
C4 C5 1.395(2) .
C5 C6 1.395(2) .
C6 C7 1.374(3) .
C7 C8 1.388(3) .
C8 C9 1.390(2) .
C11 C12 1.444(5) .
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_1
_geom_torsion_site_symmetry_4
C3 C1 C2 F1 179.65(15) 5_556 .
I1 C1 C2 F1 1.1(2) . .
C3 C1 C2 C3 0.6(3) 5_556 .
I1 C1 C2 C3 -177.93(13) . .
F1 C2 C3 F2 1.1(2) . .
C1 C2 C3 F2 -179.77(16) . .
F1 C2 C3 C1 -179.70(15) . 5_556
C1 C2 C3 C1 -0.6(3) . 5_556
O1 P2 C4 C9 -13.68(15) . .
C10 P2 C4 C9 -138.94(14) . .
C4 P2 C4 C9 107.55(13) 7_565 .
O1 P2 C4 C5 170.00(14) . .
C10 P2 C4 C5 44.75(16) . .
C4 P2 C4 C5 -68.76(17) 7_565 .
C9 C4 C5 C6 -1.4(3) . .
P2 C4 C5 C6 174.90(15) . .
C4 C5 C6 C7 1.4(3) . .
C5 C6 C7 C8 -0.2(3) . .
C6 C7 C8 C9 -1.0(3) . .
C7 C8 C9 C4 0.9(3) . .
C5 C4 C9 C8 0.3(2) . .
P2 C4 C9 C8 -176.12(13) . .
