#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:38:07 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178475 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/96/4029635.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_4029635
loop_
_publ_author_name
'Widner, Danielle L.'
'Knauf, Qianwei R.'
'Merucci, Mark T.'
'Fritz, Thomas R.'
'Sauer, Jon S.'
'Speetzen, Erin D.'
'Bosch, Eric'
'Bowling, Nathan P.'
_publ_section_title
;
 Intramolecular halogen bonding supported by an aryldiyne linker.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6269
_journal_page_last               6278
_journal_paper_doi               10.1021/jo501015x
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C25 H10 Br F4 N'
_chemical_formula_weight         480.25
_chemical_name_systematic
;
 ?
;
_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-2013
_cell_angle_alpha                90
_cell_angle_beta                 101.726(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1682(11)
_cell_length_b                   7.7306(8)
_cell_length_c                   21.808(2)
_cell_measurement_reflns_used    5936
_cell_measurement_temperature    99(2)
_cell_measurement_theta_max      27.14
_cell_measurement_theta_min      2.38
_cell_volume                     1843.5(3)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      99(2)
_diffrn_detector_area_resol_mean 8.3660
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-I CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            12934
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.156
_diffrn_reflns_theta_min         1.862
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.282
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4088
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0258
_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)+(0.0348P)²+1.6253P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0654
_refine_ls_wR_factor_ref         0.0678
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3638
_reflns_number_total             4088
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo501015x_si_001.cif
_cod_data_source_block           20
_cod_depositor_comments
'Adding full bibliography for 4029631--4029636.cif.'
_cod_database_code               4029635
#BEGIN Tags that were not found in dictionaries:
_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   0.658
_shelx_estimated_absorpt_t_max   0.914
_shelxl_version_number           2013-2
#END Tags that were not found in dictionaries
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
Br1 Br 0.53467(2) 0.78633(2) 0.05588(2) 0.01393(7) Uani 1 1 d . .
F1 F 0.35010(11) 0.60714(16) 0.11939(5) 0.0195(3) Uani 1 1 d . .
N1 N 0.76592(14) 0.9584(2) 0.09853(7) 0.0133(3) Uani 1 1 d . .
C1 C 0.81292(17) 0.9990(3) 0.15967(9) 0.0131(4) Uani 1 1 d . .
F2 F 0.14892(11) 0.42638(16) 0.06861(6) 0.0200(3) Uani 1 1 d . .
C2 C 0.74921(18) 0.9413(3) 0.20590(9) 0.0164(4) Uani 1 1 d . .
H2 H 0.6756 0.8772 0.1938 0.020 Uiso 1 1 calc R U
F3 F 0.08545(10) 0.38149(16) -0.05741(6) 0.0195(3) Uani 1 1 d . .
C3 C 0.79325(19) 0.9776(3) 0.26787(9) 0.0186(4) Uani 1 1 d . .
H3 H 0.7496 0.9391 0.2984 0.022 Uiso 1 1 calc R U
F4 F 0.22499(11) 0.51757(16) -0.13261(5) 0.0196(3) Uani 1 1 d . .
C4 C 0.90306(19) 1.0717(3) 0.28672(9) 0.0180(4) Uani 1 1 d . .
H4 H 0.9335 1.0941 0.3299 0.022 Uiso 1 1 calc R U
C5 C 0.96591(18) 1.1309(3) 0.24309(9) 0.0177(4) Uani 1 1 d . .
H5 H 1.0390 1.1954 0.2562 0.021 Uiso 1 1 calc R U
C6 C 0.92228(17) 1.0962(2) 0.17833(9) 0.0134(4) Uani 1 1 d . .
C7 C 0.98170(17) 1.1546(3) 0.13070(9) 0.0155(4) Uani 1 1 d . .
H7 H 1.0541 1.2221 0.1412 0.019 Uiso 1 1 calc R U
C8 C 0.93461(17) 1.1136(3) 0.06973(9) 0.0152(4) Uani 1 1 d . .
H8 H 0.9741 1.1508 0.0374 0.018 Uiso 1 1 calc R U
C9 C 0.82504(17) 1.0140(2) 0.05542(9) 0.0124(4) Uani 1 1 d . .
C10 C 0.77258(17) 0.9761(3) -0.00931(9) 0.0142(4) Uani 1 1 d . .
C11 C 0.72904(17) 0.9568(2) -0.06366(9) 0.0138(4) Uani 1 1 d . .
C12 C 0.68328(17) 0.9475(2) -0.12995(9) 0.0128(4) Uani 1 1 d . .
C13 C 0.74849(18) 1.0331(3) -0.16969(9) 0.0146(4) Uani 1 1 d . .
H13 H 0.8211 1.0944 -0.1521 0.018 Uiso 1 1 calc R U
C14 C 0.70864(18) 1.0295(3) -0.23392(9) 0.0159(4) Uani 1 1 d . .
H14 H 0.7541 1.0872 -0.2602 0.019 Uiso 1 1 calc R U
C15 C 0.60160(18) 0.9412(3) -0.26016(9) 0.0161(4) Uani 1 1 d . .
H15 H 0.5744 0.9381 -0.3044 0.019 Uiso 1 1 calc R U
C16 C 0.53493(18) 0.8580(3) -0.22198(9) 0.0152(4) Uani 1 1 d . .
H16 H 0.4617 0.7991 -0.2403 0.018 Uiso 1 1 calc R U
C17 C 0.57376(17) 0.8594(2) -0.15664(9) 0.0130(4) Uani 1 1 d . .
C18 C 0.50090(18) 0.7761(3) -0.11793(9) 0.0139(4) Uani 1 1 d . .
C19 C 0.43696(17) 0.7115(3) -0.08658(9) 0.0142(4) Uani 1 1 d . .
C20 C 0.36313(17) 0.6394(2) -0.04620(9) 0.0124(4) Uani 1 1 d . .
C21 C 0.39466(17) 0.6610(2) 0.01927(9) 0.0131(4) Uani 1 1 d . .
C22 C 0.32221(18) 0.5882(3) 0.05671(9) 0.0143(4) Uani 1 1 d . .
C23 C 0.21856(17) 0.4947(3) 0.03118(9) 0.0147(4) Uani 1 1 d . .
C24 C 0.18631(17) 0.4725(3) -0.03273(9) 0.0148(4) Uani 1 1 d . .
C25 C 0.25824(17) 0.5440(3) -0.07062(9) 0.0139(4) 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
C9 N1 C1 117.99(16)
N1 C1 C2 118.18(17)
N1 C1 C6 122.57(17)
C2 C1 C6 119.25(17)
C3 C2 C1 120.36(19)
C2 C3 C4 120.56(19)
C5 C4 C3 120.44(19)
C4 C5 C6 120.38(19)
C7 C6 C1 117.53(17)
C7 C6 C5 123.46(18)
C1 C6 C5 119.00(18)
C8 C7 C6 119.73(18)
C7 C8 C9 118.85(18)
N1 C9 C8 123.31(17)
N1 C9 C10 117.75(17)
C8 C9 C10 118.91(17)
C11 C10 C9 175.4(2)
C10 C11 C12 174.6(2)
C13 C12 C17 119.01(17)
C13 C12 C11 118.35(17)
C17 C12 C11 122.62(17)
C14 C13 C12 121.01(18)
C13 C14 C15 119.92(18)
C16 C15 C14 120.12(18)
C15 C16 C17 121.00(18)
C16 C17 C12 118.91(17)
C16 C17 C18 119.87(17)
C12 C17 C18 121.19(17)
C19 C18 C17 177.5(2)
C18 C19 C20 177.0(2)
C25 C20 C21 117.84(17)
C25 C20 C19 120.91(17)
C21 C20 C19 121.25(17)
C22 C21 C20 119.67(18)
C22 C21 Br1 119.80(15)
C20 C21 Br1 120.52(14)
F1 C22 C21 120.91(17)
F1 C22 C23 117.87(17)
C21 C22 C23 121.22(18)
F2 C23 C24 120.06(17)
F2 C23 C22 120.08(17)
C24 C23 C22 119.86(18)
F3 C24 C23 119.71(17)
F3 C24 C25 120.83(18)
C23 C24 C25 119.46(18)
F4 C25 C24 117.81(17)
F4 C25 C20 120.23(17)
C24 C25 C20 121.95(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C21 1.8745(19)
F1 C22 1.347(2)
N1 C9 1.326(2)
N1 C1 1.367(2)
C1 C2 1.419(3)
C1 C6 1.421(3)
F2 C23 1.345(2)
C2 C3 1.370(3)
F3 C24 1.344(2)
C3 C4 1.413(3)
F4 C25 1.343(2)
C4 C5 1.371(3)
C5 C6 1.423(3)
C6 C7 1.415(3)
C7 C8 1.364(3)
C8 C9 1.426(3)
C9 C10 1.444(3)
C10 C11 1.195(3)
C11 C12 1.434(3)
C12 C13 1.406(3)
C12 C17 1.418(3)
C13 C14 1.381(3)
C14 C15 1.395(3)
C15 C16 1.383(3)
C16 C17 1.403(3)
C17 C18 1.438(3)
C18 C19 1.194(3)
C19 C20 1.436(3)
C20 C25 1.395(3)
C20 C21 1.409(3)
C21 C22 1.381(3)
C22 C23 1.383(3)
C23 C24 1.378(3)
C24 C25 1.379(3)
