#------------------------------------------------------------------------------
#$Date: 2015-05-13 11:33:30 +0300 (Wed, 13 May 2015) $
#$Revision: 136163 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/71/7117158.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_7117158
loop_
_publ_author_name
'Fanny Frausto'
'Zachary C. Smith'
'Terry E. Haas'
'Samuel W. Thomas III'
_publ_section_title
;
 Two-dimensional bricklayer arrangements of tolans using halogen bonding
 interactions
;
_journal_name_full               Chem.Commun.
_journal_page_first              8825
_journal_paper_doi               10.1039/C5cc02225H
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C15 H4 F4 I N'
_chemical_formula_weight         401.09
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-03-16 deposited with the CCDC.
2015-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                85.468(3)
_cell_angle_beta                 75.250(3)
_cell_angle_gamma                67.203(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4665(9)
_cell_length_b                   9.3784(11)
_cell_length_c                   10.5061(13)
_cell_measurement_temperature    100(2)
_cell_volume                     655.70(14)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'omega, phi scans'
_diffrn_radiation_monochromator  Triumph
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            14322
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         41.240
_diffrn_reflns_theta_min         2.005
_diffrn_source                   'Mo sealed tube'
_exptl_absorpt_coefficient_mu    2.480
_exptl_absorpt_correction_T_max  0.748124
_exptl_absorpt_correction_T_min  0.612237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS 2008/2'
_exptl_crystal_density_diffrn    2.032
_exptl_crystal_description       prism
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.296
_exptl_crystal_size_mid          0.271
_exptl_crystal_size_min          0.136
_refine_diff_density_max         3.231
_refine_diff_density_min         -2.182
_refine_diff_density_rms         0.240
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         7696
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0416
_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)+(0.0487P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0917
_reflns_Friedel_coverage         0.000
_reflns_friedel_fraction_full    .
_reflns_friedel_fraction_max     .
_reflns_number_gt                6677
_reflns_number_total             7687
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc02225h2.cif
_cod_data_source_block           FF010815cn_0t
_cod_database_code               7117158
_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   0.527
_shelx_estimated_absorpt_t_max   0.729
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
I01 I 0.77440(4) -0.54884(2) 0.75861(2) 0.01281(4) Uani 1 1 d . . . . .
F01 F 0.4785(3) -0.2833(2) 0.97527(18) 0.0190(4) Uani 1 1 d . . . . .
F02 F 0.3209(3) 0.0244(2) 0.96225(19) 0.0203(4) Uani 1 1 d . . . . .
F03 F 0.6866(3) -0.0057(2) 0.51914(19) 0.0207(4) Uani 1 1 d . . . . .
F04 F 0.8295(3) -0.3140(2) 0.52749(18) 0.0177(4) Uani 1 1 d . . . . .
N01 N -0.0563(8) 1.1087(3) 0.7687(5) 0.0310(7) Uani 1 1 d . . . . .
C01 C 0.6574(7) -0.3095(2) 0.7513(3) 0.0105(3) Uani 1 1 d . . . . .
C02 C 0.5285(5) -0.2173(4) 0.8611(3) 0.0140(5) Uani 1 1 d . . . . .
C03 C 0.4490(5) -0.0572(4) 0.8552(3) 0.0139(5) Uani 1 1 d . . . . .
C04 C 0.4987(8) 0.0191(3) 0.7413(4) 0.0147(5) Uani 1 1 d . . . . .
C05 C 0.6309(5) -0.0729(3) 0.6317(3) 0.0132(5) Uani 1 1 d . . . . .
C06 C 0.7060(5) -0.2318(3) 0.6365(3) 0.0116(5) Uani 1 1 d . . . . .
C07 C 0.4186(6) 0.1841(3) 0.7354(3) 0.0161(5) Uani 1 1 d . . . . .
C08 C 0.3486(7) 0.3227(3) 0.7364(4) 0.0162(5) Uani 1 1 d . . . . .
C09 C 0.2630(6) 0.4884(3) 0.7417(3) 0.0136(4) Uani 1 1 d . . . . .
C10 C 0.1862(5) 0.5651(5) 0.8646(3) 0.0174(6) Uani 1 1 d . . . . .
H01 H 0.1902 0.5075 0.9431 0.021 Uiso 1 1 calc R U . . .
C11 C 0.1036(5) 0.7267(4) 0.8714(3) 0.0172(6) Uani 1 1 d . . . . .
H02 H 0.0517 0.7796 0.9543 0.021 Uiso 1 1 calc R U . . .
C12 C 0.0981(8) 0.8092(3) 0.7559(4) 0.0162(5) Uani 1 1 d . . . . .
C13 C 0.1745(6) 0.7340(4) 0.6321(3) 0.0174(6) Uani 1 1 d . . . . .
H03 H 0.1708 0.7921 0.5538 0.021 Uiso 1 1 calc R U . . .
C14 C 0.2558(5) 0.5732(4) 0.6259(3) 0.0151(6) Uani 1 1 d . . . . .
H04 H 0.3065 0.5206 0.5429 0.018 Uiso 1 1 calc R U . . .
C15 C 0.0131(8) 0.9764(3) 0.7615(4) 0.0213(6) 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'
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
C02 C01 C06 116.5(2) . .
C02 C01 I01 121.8(2) . .
C06 C01 I01 121.7(2) . .
F01 C02 C03 118.5(3) . .
F01 C02 C01 120.0(3) . .
C03 C02 C01 121.5(3) . .
F02 C03 C02 118.7(3) . .
F02 C03 C04 119.7(3) . .
C02 C03 C04 121.6(3) . .
C03 C04 C05 117.0(2) . .
C03 C04 C07 121.7(4) . .
C05 C04 C07 121.3(3) . .
F03 C05 C06 118.8(3) . .
F03 C05 C04 119.7(3) . .
C06 C05 C04 121.4(3) . .
F04 C06 C05 118.7(3) . .
F04 C06 C01 119.4(3) . .
C05 C06 C01 121.9(3) . .
C08 C07 C04 177.1(4) . .
C07 C08 C09 178.3(4) . .
C14 C09 C10 120.2(2) . .
C14 C09 C08 120.7(3) . .
C10 C09 C08 119.1(3) . .
C11 C10 C09 119.8(3) . .
C11 C10 H01 120.1 . .
C09 C10 H01 120.1 . .
C12 C11 C10 119.4(3) . .
C12 C11 H02 120.3 . .
C10 C11 H02 120.3 . .
C11 C12 C13 121.5(2) . .
C11 C12 C15 120.0(4) . .
C13 C12 C15 118.5(4) . .
C14 C13 C12 118.9(3) . .
C14 C13 H03 120.6 . .
C12 C13 H03 120.6 . .
C13 C14 C09 120.2(3) . .
C13 C14 H04 119.9 . .
C09 C14 H04 119.9 . .
N01 C15 C12 178.5(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I01 C01 2.073(2) .
F01 C02 1.340(3) .
F02 C03 1.337(3) .
F03 C05 1.343(3) .
F04 C06 1.344(3) .
N01 C15 1.144(3) .
C01 C02 1.397(4) .
C01 C06 1.400(4) .
C02 C03 1.387(4) .
C03 C04 1.388(5) .
C04 C05 1.401(5) .
C04 C07 1.429(3) .
C05 C06 1.375(4) .
C07 C08 1.198(3) .
C08 C09 1.432(3) .
C09 C14 1.401(4) .
C09 C10 1.401(4) .
C10 C11 1.397(5) .
C10 H01 0.9500 .
C11 C12 1.387(5) .
C11 H02 0.9500 .
C12 C13 1.403(5) .
C12 C15 1.446(3) .
C13 C14 1.391(5) .
C13 H03 0.9500 .
C14 H04 0.9500 .
