#------------------------------------------------------------------------------
#$Date: 2025-08-22 14:50:14 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301863 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/32/7203235.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_7203235
loop_
_publ_author_name
'Mariaca, Raúl'
'Behrnd, Norwid-Rasmus'
'Eggli, Patrick'
'Stoeckli-Evans, Helen'
'Hulliger, Jürg'
_publ_section_title
;
 Synthesis and crystal engineering of fluorinated stilbenes
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              222
_journal_paper_doi               10.1039/b517032j
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C15 H6 Br F4 N'
_chemical_formula_sum            'C15 H6 Br F4 N'
_chemical_formula_weight         356.12
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.193(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3134(10)
_cell_length_b                   11.0006(8)
_cell_length_c                   12.5519(14)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      26.02
_cell_measurement_theta_min      2.20
_cell_volume                     1275.9(2)
_computing_cell_refinement       'CELL (Stoe IPDS Software, 2000)'
_computing_data_collection       'EXPOSE (Stoe IPDS Software, 2000)'
_computing_data_reduction        'INTEGRATE (Stoe IPDS Software, 2000)'
_computing_molecular_graphics    'PLATON99 (Spek, 2003)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'STOE IPDS'
_diffrn_measurement_method       'phi oscillation'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9773
_diffrn_reflns_theta_full        26.06
_diffrn_reflns_theta_max         26.06
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.261
_exptl_absorpt_correction_T_max  0.235
_exptl_absorpt_correction_T_min  0.167
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'MULscanABS in PLATON (Spek, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.854
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2493
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0468P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0702
_reflns_number_gt                2083
_reflns_number_total             2493
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            b517032j.txt
_cod_data_source_block           CF4H4B
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7203235
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.21979(3) 0.07693(2) -0.150836(18) 0.02880(10) Uani 1 1 d . . .
F1 F 0.45793(17) 0.53446(14) 0.18992(11) 0.0370(4) Uani 1 1 d . . .
F2 F 0.65325(17) 0.70095(14) 0.25617(11) 0.0383(4) Uani 1 1 d . . .
F3 F 0.54572(16) 0.91375(11) -0.06847(11) 0.0307(3) Uani 1 1 d . . .
F4 F 0.34613(17) 0.75050(13) -0.13608(10) 0.0338(3) Uani 1 1 d . . .
N1 N 0.8016(2) 0.9684(2) 0.16487(17) 0.0344(5) Uani 1 1 d . . .
C1 C -0.0865(2) 0.19833(19) -0.09550(18) 0.0231(5) Uani 1 1 d . . .
C2 C -0.0268(3) 0.1911(2) 0.01064(18) 0.0263(5) Uani 1 1 d . . .
H2A H -0.0532 0.1274 0.0555 0.032 Uiso 1 1 calc R . .
C3 C 0.0725(3) 0.2788(2) 0.05028(18) 0.0269(5) Uani 1 1 d . . .
H3A H 0.1136 0.2752 0.1234 0.032 Uiso 1 1 calc R . .
C4 C 0.1136(2) 0.3724(2) -0.01467(18) 0.0231(5) Uani 1 1 d . . .
C5 C 0.0482(3) 0.3784(2) -0.12094(18) 0.0251(5) Uani 1 1 d . . .
H5A H 0.0731 0.4426 -0.1658 0.030 Uiso 1 1 calc R . .
C6 C -0.0525(3) 0.2921(2) -0.16196(18) 0.0251(5) Uani 1 1 d . . .
H6A H -0.0972 0.2971 -0.2341 0.030 Uiso 1 1 calc R . .
C7 C 0.2231(3) 0.4593(2) 0.03259(18) 0.0253(5) Uani 1 1 d . . .
H7A H 0.2563 0.4508 0.1069 0.030 Uiso 1 1 calc R . .
C8 C 0.2799(3) 0.5491(2) -0.02001(18) 0.0248(5) Uani 1 1 d . . .
H8A H 0.2453 0.5573 -0.0941 0.030 Uiso 1 1 calc R . .
C9 C 0.3895(2) 0.6359(2) 0.02435(17) 0.0219(5) Uani 1 1 d . . .
C10 C 0.4728(3) 0.6289(2) 0.12438(19) 0.0253(5) Uani 1 1 d . . .
C11 C 0.5766(3) 0.7136(2) 0.15957(18) 0.0257(5) Uani 1 1 d . . .
C12 C 0.6049(2) 0.8121(2) 0.09615(18) 0.0230(5) Uani 1 1 d . . .
C13 C 0.5235(3) 0.82086(19) -0.00416(18) 0.0237(5) Uani 1 1 d . . .
C14 C 0.4206(2) 0.7359(2) -0.03808(17) 0.0230(5) Uani 1 1 d . . .
C15 C 0.7140(3) 0.8997(2) 0.13345(18) 0.0265(5) 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'
Br Br -0.2901 2.4595 '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'
N N 0.0061 0.0033 '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
_geom_angle_publ_flag
C2 C1 C6 121.9(2) . . ?
C2 C1 Br1 118.63(16) . . ?
C6 C1 Br1 119.48(17) . . ?
C1 C2 C3 118.4(2) . . ?
C1 C2 H2A 120.8 . . ?
C3 C2 H2A 120.8 . . ?
C2 C3 C4 121.6(2) . . ?
C2 C3 H3A 119.2 . . ?
C4 C3 H3A 119.2 . . ?
C3 C4 C5 118.3(2) . . ?
C3 C4 C7 118.1(2) . . ?
C5 C4 C7 123.6(2) . . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 H5A 119.5 . . ?
C4 C5 H5A 119.5 . . ?
C5 C6 C1 118.7(2) . . ?
C5 C6 H6A 120.7 . . ?
C1 C6 H6A 120.7 . . ?
C8 C7 C4 125.5(2) . . ?
C8 C7 H7A 117.2 . . ?
C4 C7 H7A 117.2 . . ?
C7 C8 C9 126.8(2) . . ?
C7 C8 H8A 116.6 . . ?
C9 C8 H8A 116.6 . . ?
C10 C9 C14 114.7(2) . . ?
C10 C9 C8 126.3(2) . . ?
C14 C9 C8 119.0(2) . . ?
F1 C10 C11 116.7(2) . . ?
F1 C10 C9 120.5(2) . . ?
C11 C10 C9 122.8(2) . . ?
F2 C11 C10 119.7(2) . . ?
F2 C11 C12 118.9(2) . . ?
C10 C11 C12 121.4(2) . . ?
C11 C12 C13 116.9(2) . . ?
C11 C12 C15 120.9(2) . . ?
C13 C12 C15 122.2(2) . . ?
F3 C13 C14 119.4(2) . . ?
F3 C13 C12 119.6(2) . . ?
C14 C13 C12 121.0(2) . . ?
F4 C14 C13 117.7(2) . . ?
F4 C14 C9 119.12(19) . . ?
C13 C14 C9 123.2(2) . . ?
N1 C15 C12 178.8(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.895(2) . ?
F1 C10 1.343(3) . ?
F2 C11 1.335(3) . ?
F3 C13 1.334(2) . ?
F4 C14 1.344(3) . ?
N1 C15 1.146(3) . ?
C1 C2 1.380(3) . ?
C1 C6 1.389(3) . ?
C2 C3 1.386(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.396(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.397(3) . ?
C4 C7 1.467(3) . ?
C5 C6 1.387(3) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.334(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.457(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.393(3) . ?
C9 C14 1.401(3) . ?
C10 C11 1.375(3) . ?
C11 C12 1.388(3) . ?
C12 C13 1.389(3) . ?
C12 C15 1.436(3) . ?
C13 C14 1.368(3) . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.6(3) . . . . ?
Br1 C1 C2 C3 178.88(18) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C3 C4 C5 2.1(4) . . . . ?
C2 C3 C4 C7 -178.0(2) . . . . ?
C3 C4 C5 C6 -1.5(3) . . . . ?
C7 C4 C5 C6 178.6(2) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C2 C1 C6 C5 2.2(3) . . . . ?
Br1 C1 C6 C5 -178.29(17) . . . . ?
C3 C4 C7 C8 175.9(2) . . . . ?
C5 C4 C7 C8 -4.2(4) . . . . ?
C4 C7 C8 C9 -179.4(2) . . . . ?
C7 C8 C9 C10 11.8(4) . . . . ?
C7 C8 C9 C14 -170.2(2) . . . . ?
C14 C9 C10 F1 -177.1(2) . . . . ?
C8 C9 C10 F1 1.1(4) . . . . ?
C14 C9 C10 C11 0.5(3) . . . . ?
C8 C9 C10 C11 178.6(2) . . . . ?
F1 C10 C11 F2 -2.0(3) . . . . ?
C9 C10 C11 F2 -179.6(2) . . . . ?
F1 C10 C11 C12 177.3(2) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
F2 C11 C12 C13 179.4(2) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
F2 C11 C12 C15 -0.3(3) . . . . ?
C10 C11 C12 C15 -179.7(2) . . . . ?
C11 C12 C13 F3 179.8(2) . . . . ?
C15 C12 C13 F3 -0.5(3) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C15 C12 C13 C14 179.6(2) . . . . ?
F3 C13 C14 F4 0.1(3) . . . . ?
C12 C13 C14 F4 180.0(2) . . . . ?
F3 C13 C14 C9 -179.6(2) . . . . ?
C12 C13 C14 C9 0.3(4) . . . . ?
C10 C9 C14 F4 179.9(2) . . . . ?
C8 C9 C14 F4 1.6(3) . . . . ?
C10 C9 C14 C13 -0.5(3) . . . . ?
C8 C9 C14 C13 -178.7(2) . . . . ?
C11 C12 C15 N1 -1(13) . . . . ?
C13 C12 C15 N1 179(100) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21197856
2 PubChem 139195055
