#------------------------------------------------------------------------------
#$Date: 2015-05-13 11:33:30 +0300 (Wed, 13 May 2015) $
#$Revision: 136163 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/71/7117160.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_7117160
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 Br F4 N'
_chemical_formula_weight         354.10
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                90
_cell_angle_beta                 102.415(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.2997(14)
_cell_length_b                   9.7019(11)
_cell_length_c                   19.917(2)
_cell_measurement_temperature    100(2)
_cell_volume                     2509.8(5)
_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 0.999
_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  0.0386
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            72556
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.971
_diffrn_reflns_theta_min         2.620
_diffrn_source                   'Mo sealed tube'
_exptl_absorpt_coefficient_mu    3.315
_exptl_absorpt_correction_T_max  0.907
_exptl_absorpt_correction_T_min  0.659
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.874
_exptl_crystal_description       prism
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.742
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.096
_refine_diff_density_max         1.233
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.120
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         11025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0297
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0379P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0638
_refine_ls_wR_factor_ref         0.0696
_reflns_Friedel_coverage         0.000
_reflns_friedel_fraction_full    .
_reflns_friedel_fraction_max     .
_reflns_number_gt                8677
_reflns_number_total             11025
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc02225h2.cif
_cod_data_source_block           RP-4_a
_cod_database_code               7117160
_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   0.192
_shelx_estimated_absorpt_t_max   0.741
loop_
_space_group_symop_operation_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_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
Br01 Br 0.78495(2) 0.47606(2) 0.12705(2) 0.01532(3) Uani 1 1 d . . . . .
Br02 Br 0.53552(2) 0.01079(2) 0.39209(2) 0.01711(3) Uani 1 1 d . . . . .
F1 F 0.98848(5) 0.35148(7) 0.20316(4) 0.01705(14) Uani 1 1 d . . . . .
F2 F 1.02322(5) 0.16523(7) 0.30354(4) 0.01664(14) Uani 1 1 d . . . . .
F3 F 0.66662(5) 0.13484(8) 0.29372(4) 0.02037(15) Uani 1 1 d . . . . .
F4 F 0.63157(5) 0.32516(8) 0.19555(4) 0.02094(15) Uani 1 1 d . . . . .
F05 F 0.73963(5) 0.14658(7) 0.45951(3) 0.01654(14) Uani 1 1 d . . . . .
F06 F 0.77542(5) 0.34979(7) 0.55252(4) 0.01772(14) Uani 1 1 d . . . . .
F07 F 0.42045(5) 0.37320(8) 0.54994(4) 0.01966(15) Uani 1 1 d . . . . .
F08 F 0.38418(5) 0.17551(8) 0.45455(4) 0.02000(15) Uani 1 1 d . . . . .
N01 N 0.98271(9) -0.52737(11) 0.65219(6) 0.0231(2) Uani 1 1 d . . . . .
N02 N 0.73265(9) 1.06674(12) 0.88929(6) 0.0261(2) Uani 1 1 d . . . . .
C01 C 0.80949(8) 0.34369(11) 0.19656(5) 0.01195(19) Uani 1 1 d . . . . .
C02 C 0.90864(8) 0.29995(11) 0.22523(6) 0.01162(19) Uani 1 1 d . . . . .
C03 C 0.92631(8) 0.20215(11) 0.27684(5) 0.01129(19) Uani 1 1 d . . . . .
C04 C 0.84628(8) 0.14231(11) 0.30187(5) 0.01157(19) Uani 1 1 d . . . . .
C05 C 0.74719(9) 0.18764(11) 0.27232(6) 0.0130(2) Uani 1 1 d . . . . .
C06 C 0.72901(8) 0.28613(11) 0.22117(6) 0.0132(2) Uani 1 1 d . . . . .
C07 C 0.86492(9) 0.04025(11) 0.35432(6) 0.0133(2) Uani 1 1 d . . . . .
C08 C 0.88074(9) -0.04711(12) 0.39816(6) 0.0136(2) Uani 1 1 d . . . . .
C09 C 0.90134(9) -0.15065(11) 0.45034(5) 0.01236(19) Uani 1 1 d . . . . .
C10 C 1.00202(9) -0.19739(12) 0.47480(6) 0.0158(2) Uani 1 1 d . . . . .
H01 H 1.0566 -0.1610 0.4563 0.019 Uiso 1 1 calc R U . . .
C11 C 1.02255(9) -0.29689(12) 0.52610(6) 0.0156(2) Uani 1 1 d . . . . .
H00S H 1.0909 -0.3286 0.5428 0.019 Uiso 1 1 calc R U . . .
C12 C 0.94187(9) -0.34974(11) 0.55285(6) 0.0135(2) Uani 1 1 d . . . . .
C13 C 0.84099(9) -0.30482(12) 0.52831(6) 0.0169(2) Uani 1 1 d . . . . .
H00Z H 0.7864 -0.3423 0.5465 0.020 Uiso 1 1 calc R U . . .
C14 C 0.82085(9) -0.20537(12) 0.47729(6) 0.0162(2) Uani 1 1 d . . . . .
H016 H 0.7523 -0.1742 0.4605 0.019 Uiso 1 1 calc R U . . .
C15 C 0.96441(9) -0.44975(13) 0.60772(6) 0.0168(2) Uani 1 1 d . . . . .
C16 C 0.56104(9) 0.15719(11) 0.45435(5) 0.01259(19) Uani 1 1 d . . . . .
C17 C 0.66019(8) 0.20399(11) 0.48000(5) 0.01204(19) Uani 1 1 d . . . . .
C18 C 0.67843(8) 0.30821(11) 0.52833(6) 0.01238(19) Uani 1 1 d . . . . .
C19 C 0.59917(8) 0.36787(11) 0.55384(5) 0.01211(19) Uani 1 1 d . . . . .
C20 C 0.49968(9) 0.32035(11) 0.52690(6) 0.0134(2) Uani 1 1 d . . . . .
C21 C 0.48093(9) 0.21803(12) 0.47781(6) 0.0134(2) Uani 1 1 d . . . . .
C22 C 0.61896(9) 0.47009(12) 0.60623(6) 0.0151(2) Uani 1 1 d . . . . .
C23 C 0.63567(9) 0.55516(12) 0.65137(6) 0.0153(2) Uani 1 1 d . . . . .
C24 C 0.65641(9) 0.65809(11) 0.70398(6) 0.0134(2) Uani 1 1 d . . . . .
C25 C 0.75756(9) 0.70251(12) 0.72924(6) 0.0158(2) Uani 1 1 d . . . . .
H015 H 0.8125 0.6619 0.7126 0.019 Uiso 1 1 calc R U . . .
C26 C 0.77783(9) 0.80596(12) 0.77853(6) 0.0159(2) Uani 1 1 d . . . . .
H00X H 0.8463 0.8369 0.7956 0.019 Uiso 1 1 calc R U . . .
C27 C 0.69627(9) 0.86386(11) 0.80271(6) 0.0145(2) Uani 1 1 d . . . . .
C28 C 0.59516(9) 0.81812(12) 0.77870(6) 0.0183(2) Uani 1 1 d . . . . .
H011 H 0.5404 0.8574 0.7960 0.022 Uiso 1 1 calc R U . . .
C29 C 0.57552(9) 0.71524(12) 0.72957(6) 0.0179(2) Uani 1 1 d . . . . .
H013 H 0.5071 0.6833 0.7132 0.022 Uiso 1 1 calc R U . . .
C30 C 0.71667(10) 0.97579(12) 0.85126(7) 0.0181(2) 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C02 C01 C06 117.99(10) . .
C02 C01 Br01 121.05(8) . .
C06 C01 Br01 120.96(8) . .
F1 C02 C03 118.93(9) . .
F1 C02 C01 120.31(9) . .
C03 C02 C01 120.76(10) . .
F2 C03 C02 118.46(9) . .
F2 C03 C04 119.47(9) . .
C02 C03 C04 122.07(10) . .
C05 C04 C03 116.27(10) . .
C05 C04 C07 121.97(10) . .
C03 C04 C07 121.76(10) . .
F3 C05 C06 118.39(10) . .
F3 C05 C04 119.62(10) . .
C06 C05 C04 122.00(10) . .
F4 C06 C05 118.56(10) . .
F4 C06 C01 120.52(10) . .
C05 C06 C01 120.92(10) . .
C08 C07 C04 179.31(13) . .
C07 C08 C09 179.04(13) . .
C10 C09 C14 119.80(10) . .
C10 C09 C08 120.05(10) . .
C14 C09 C08 120.14(10) . .
C11 C10 C09 120.23(11) . .
C10 C11 C12 119.40(10) . .
C11 C12 C13 120.81(10) . .
C11 C12 C15 119.00(10) . .
C13 C12 C15 120.17(10) . .
C14 C13 C12 119.63(11) . .
C13 C14 C09 120.12(11) . .
N01 C15 C12 178.76(14) . .
C21 C16 C17 118.47(10) . .
C21 C16 Br02 120.34(8) . .
C17 C16 Br02 121.14(8) . .
F05 C17 C18 119.15(9) . .
F05 C17 C16 120.30(10) . .
C18 C17 C16 120.54(10) . .
F06 C18 C17 118.87(10) . .
F06 C18 C19 119.38(10) . .
C17 C18 C19 121.72(10) . .
C18 C19 C20 116.92(10) . .
C18 C19 C22 121.52(10) . .
C20 C19 C22 121.55(10) . .
F07 C20 C21 118.92(10) . .
F07 C20 C19 119.54(10) . .
C21 C20 C19 121.53(10) . .
F08 C21 C20 118.84(10) . .
F08 C21 C16 120.35(10) . .
C20 C21 C16 120.78(10) . .
C23 C22 C19 178.99(13) . .
C22 C23 C24 178.75(13) . .
C25 C24 C29 120.12(10) . .
C25 C24 C23 119.82(10) . .
C29 C24 C23 120.05(10) . .
C26 C25 C24 120.14(11) . .
C25 C26 C27 119.17(11) . .
C26 C27 C28 121.03(10) . .
C26 C27 C30 119.13(11) . .
C28 C27 C30 119.80(11) . .
C29 C28 C27 119.49(11) . .
C28 C29 C24 120.03(11) . .
N02 C30 C27 178.96(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br01 C01 1.8649(11) .
Br02 C16 1.8680(11) .
F1 C02 1.3310(12) .
F2 C03 1.3333(12) .
F3 C05 1.3374(13) .
F4 C06 1.3412(12) .
F05 C17 1.3337(12) .
F06 C18 1.3385(12) .
F07 C20 1.3385(12) .
F08 C21 1.3358(13) .
N01 C15 1.1481(16) .
N02 C30 1.1524(16) .
C01 C02 1.3861(15) .
C01 C06 1.3869(15) .
C02 C03 1.3812(15) .
C03 C04 1.3952(15) .
C04 C05 1.3939(15) .
C04 C07 1.4219(15) .
C05 C06 1.3796(15) .
C07 C08 1.2026(16) .
C08 C09 1.4289(15) .
C09 C10 1.3984(16) .
C09 C14 1.4010(15) .
C10 C11 1.3894(16) .
C11 C12 1.3943(16) .
C12 C13 1.3953(16) .
C12 C15 1.4438(16) .
C13 C14 1.3849(15) .
C16 C21 1.3842(15) .
C16 C17 1.3843(15) .
C17 C18 1.3811(15) .
C18 C19 1.3910(15) .
C19 C20 1.3949(15) .
C19 C22 1.4225(16) .
C20 C21 1.3780(16) .
C22 C23 1.2054(16) .
C23 C24 1.4307(16) .
C24 C25 1.3991(16) .
C24 C29 1.4001(16) .
C25 C26 1.3892(15) .
C26 C27 1.3960(16) .
C27 C28 1.3991(16) .
C27 C30 1.4406(16) .
C28 C29 1.3828(16) .
