#------------------------------------------------------------------------------
#$Date: 2018-09-10 05:06:28 +0300 (Mon, 10 Sep 2018) $
#$Revision: 210724 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/79/7117999.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_7117999
loop_
_publ_author_name
'Schickedanz, Kai'
'Trageser, Timo'
'Bolte, Michael'
'Lerner, Hans-Wolfram'
'Wagner, Matthias'
_publ_section_title
;
 A boron-doped helicene as a highly soluble, benchtop-stable green emitter
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   87
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              15808
_journal_page_last               15810
_journal_paper_doi               10.1039/c5cc07208e
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C26 H15 B F2 I2'
_chemical_formula_sum            'C26 H15 B F2 I2'
_chemical_formula_weight         629.99
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 126.854(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.082(3)
_cell_length_b                   9.3614(8)
_cell_length_c                   14.7770(18)
_cell_measurement_reflns_used    5525
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.94
_cell_measurement_theta_min      3.44
_cell_volume                     2222.9(5)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.055
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15809
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.807
_diffrn_reflns_theta_min         3.446
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    2.857
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.882
_exptl_crystal_description       plate
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_refine_diff_density_max         1.055
_refine_diff_density_min         -1.584
_refine_diff_density_rms         0.155
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         9924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0594
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1077P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1488
_refine_ls_wR_factor_ref         0.1555
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7834
_reflns_number_total             9924
_reflns_threshold_expression     'I > 2σ(I)'
_cod_duplicate_entry             7117995
_cod_data_source_file            c5cc07208e2-3.cif
_cod_data_source_block           wa2145_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_space_group_crystal_system' value 'monoclinic ' changed to
'monoclinic' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 4093 2015-10-18 17:28:56Z antanas 
;
_cod_database_code               7117999
#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   0.502
_shelx_estimated_absorpt_t_max   0.894
_shelxl_version_number           2014/6
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.34640(4) 0.45432(7) 0.48575(5) 0.0408(3) Uani 1 1 d . . . . .
F1 F 0.5736(3) 0.3497(6) 0.6722(5) 0.0409(12) Uani 1 1 d . . . . .
B1 B 0.5000 0.5331(13) 0.7500 0.027(3) Uani 1 2 d S T P . .
C1 C 0.5000 0.3641(11) 0.7500 0.025(2) Uani 1 2 d S T P . .
C2 C 0.5376(5) 0.2814(9) 0.7132(7) 0.0282(17) Uani 1 1 d . . . . .
C3 C 0.5387(5) 0.1319(9) 0.7124(7) 0.0333(18) Uani 1 1 d . . . . .
H3 H 0.5656 0.0818 0.6865 0.040 Uiso 1 1 calc R U . . .
C4 C 0.5000 0.0593(12) 0.7500 0.034(3) Uani 1 2 d S T P . .
H4 H 0.5000 -0.0422 0.7500 0.041 Uiso 1 2 calc R U P . .
C11 C 0.4309(5) 0.6218(8) 0.7438(7) 0.0251(16) Uani 1 1 d . . . . .
C12 C 0.3416(5) 0.6090(8) 0.6691(7) 0.0261(16) Uani 1 1 d . . . . .
C13 C 0.2933(5) 0.5308(9) 0.5641(8) 0.0340(19) Uani 1 1 d . . . . .
C14 C 0.2095(6) 0.5127(11) 0.5024(9) 0.043(2) Uani 1 1 d . . . . .
H14 H 0.1808 0.4573 0.4351 0.052 Uiso 1 1 calc R U . . .
C15 C 0.1655(6) 0.5757(11) 0.5383(9) 0.045(2) Uani 1 1 d . . . . .
H15 H 0.1075 0.5587 0.4973 0.054 Uiso 1 1 calc R U . . .
C16 C 0.2053(6) 0.6604(10) 0.6307(9) 0.042(2) Uani 1 1 d . . . . .
H16 H 0.1743 0.7072 0.6514 0.051 Uiso 1 1 calc R U . . .
C17 C 0.2932(5) 0.6808(9) 0.6976(8) 0.0305(18) Uani 1 1 d . . . . .
C18 C 0.3329(6) 0.7717(9) 0.7930(9) 0.037(2) Uani 1 1 d . . . . .
H18 H 0.3006 0.8213 0.8103 0.045 Uiso 1 1 calc R U . . .
C19 C 0.4171(6) 0.7887(9) 0.8603(8) 0.037(2) Uani 1 1 d . . . . .
H19 H 0.4432 0.8502 0.9241 0.044 Uiso 1 1 calc R U . . .
C20 C 0.4651(5) 0.7155(9) 0.8352(7) 0.0302(17) Uani 1 1 d . . . . .
H20 H 0.5236 0.7303 0.8825 0.036 Uiso 1 1 calc R U . . .
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'
B B 0.0013 0.0007 '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
C11 B1 C11 116.2(9) 2_656 .
C11 B1 C1 121.9(5) 2_656 .
C11 B1 C1 121.9(5) . .
C2 C1 C2 112.8(10) 2_656 .
C2 C1 B1 123.6(5) 2_656 .
C2 C1 B1 123.6(5) . .
F1 C2 C1 118.1(7) . .
F1 C2 C3 116.9(7) . .
C1 C2 C3 124.9(8) . .
C4 C3 C2 118.2(8) . .
C4 C3 H3 120.9 . .
C2 C3 H3 120.9 . .
C3 C4 C3 120.9(11) . 2_656
C3 C4 H4 119.6 . .
C3 C4 H4 119.6 2_656 .
C20 C11 C12 117.2(7) . .
C20 C11 B1 111.7(6) . .
C12 C11 B1 130.6(7) . .
C17 C12 C11 119.1(7) . .
C17 C12 C13 114.6(7) . .
C11 C12 C13 126.3(7) . .
C14 C13 C12 123.2(9) . .
C14 C13 I1 114.7(7) . .
C12 C13 I1 121.7(5) . .
C13 C14 C15 120.0(10) . .
C13 C14 H14 120.0 . .
C15 C14 H14 120.0 . .
C16 C15 C14 120.2(9) . .
C16 C15 H15 119.9 . .
C14 C15 H15 119.9 . .
C15 C16 C17 121.0(8) . .
C15 C16 H16 119.5 . .
C17 C16 H16 119.5 . .
C18 C17 C16 119.7(8) . .
C18 C17 C12 119.8(7) . .
C16 C17 C12 120.5(8) . .
C19 C18 C17 120.6(8) . .
C19 C18 H18 119.7 . .
C17 C18 H18 119.7 . .
C18 C19 C20 119.9(8) . .
C18 C19 H19 120.0 . .
C20 C19 H19 120.0 . .
C11 C20 C19 123.0(8) . .
C11 C20 H20 118.5 . .
C19 C20 H20 118.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C13 2.115(9) .
F1 C2 1.351(10) .
B1 C11 1.572(10) 2_656
B1 C11 1.572(10) .
B1 C1 1.582(15) .
C1 C2 1.398(10) 2_656
C1 C2 1.398(10) .
C2 C3 1.401(12) .
C3 C4 1.376(11) .
C3 H3 0.9500 .
C4 C3 1.376(11) 2_656
C4 H4 0.9500 .
C11 C20 1.398(11) .
C11 C12 1.441(11) .
C12 C17 1.437(11) .
C12 C13 1.442(12) .
C13 C14 1.360(13) .
C14 C15 1.404(15) .
C14 H14 0.9500 .
C15 C16 1.351(15) .
C15 H15 0.9500 .
C16 C17 1.427(13) .
C16 H16 0.9500 .
C17 C18 1.413(13) .
C18 C19 1.362(14) .
C18 H18 0.9500 .
C19 C20 1.402(12) .
C19 H19 0.9500 .
C20 H20 0.9500 .
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
C11 B1 C1 C2 154.9(5) 2_656 . . 2_656
C11 B1 C1 C2 -25.1(5) . . . 2_656
C11 B1 C1 C2 -25.1(5) 2_656 . . .
C11 B1 C1 C2 154.9(5) . . . .
C2 C1 C2 F1 177.9(8) 2_656 . . .
B1 C1 C2 F1 -2.1(8) . . . .
C2 C1 C2 C3 -0.1(6) 2_656 . . .
B1 C1 C2 C3 179.9(6) . . . .
F1 C2 C3 C4 -177.8(6) . . . .
C1 C2 C3 C4 0.3(11) . . . .
C2 C3 C4 C3 -0.1(5) . . . 2_656
C11 B1 C11 C20 -56.8(5) 2_656 . . .
C1 B1 C11 C20 123.2(5) . . . .
C11 B1 C11 C12 131.4(9) 2_656 . . .
C1 B1 C11 C12 -48.6(9) . . . .
C20 C11 C12 C17 -6.1(11) . . . .
B1 C11 C12 C17 165.4(8) . . . .
C20 C11 C12 C13 173.1(8) . . . .
B1 C11 C12 C13 -15.5(13) . . . .
C17 C12 C13 C14 -6.8(12) . . . .
C11 C12 C13 C14 174.0(9) . . . .
C17 C12 C13 I1 166.5(6) . . . .
C11 C12 C13 I1 -12.7(11) . . . .
C12 C13 C14 C15 2.2(15) . . . .
I1 C13 C14 C15 -171.5(8) . . . .
C13 C14 C15 C16 3.4(15) . . . .
C14 C15 C16 C17 -3.9(14) . . . .
C15 C16 C17 C18 179.1(9) . . . .
C15 C16 C17 C12 -1.1(13) . . . .
C11 C12 C17 C18 5.1(11) . . . .
C13 C12 C17 C18 -174.1(8) . . . .
C11 C12 C17 C16 -174.6(7) . . . .
C13 C12 C17 C16 6.1(11) . . . .
C16 C17 C18 C19 177.7(8) . . . .
C12 C17 C18 C19 -2.0(13) . . . .
C17 C18 C19 C20 -0.1(14) . . . .
C12 C11 C20 C19 4.2(13) . . . .
B1 C11 C20 C19 -168.8(8) . . . .
C18 C19 C20 C11 -1.1(14) . . . .
