#------------------------------------------------------------------------------
#$Date: 2021-05-14 11:15:57 +0200 (vie 14 de may de 2021) $
#$Revision: 265213 $
#$URL: svn://www.crystallography.net/cod/cif/7/04/84/7048417.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_7048417
loop_
_publ_author_name
'John, Alexandra'
'Kirschner, Sven'
'Fengel, Melina K.'
'Bolte, Michael'
'Lerner, Hans-Wolfram'
'Wagner, Matthias'
_publ_section_title
;
 Simultaneous expansion of 9,10 boron-doped anthracene in longitudinal and
 lateral directions.
;
_journal_issue                   5
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1871
_journal_page_last               1877
_journal_paper_doi               10.1039/c8dt04820g
_journal_volume                  48
_journal_year                    2019
_chemical_formula_moiety         'C14 H8 Br2'
_chemical_formula_sum            'C14 H8 Br2'
_chemical_formula_weight         336.02
_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_block_doi                 10.5517/ccdc.csd.cc216r45
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2018-12-05 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.754(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.001(2)
_cell_length_b                   9.0764(6)
_cell_length_c                   7.2612(9)
_cell_measurement_reflns_used    8701
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.6
_cell_volume                     1094.0(2)
_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  SHELXL97
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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  0.1127
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7041
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         3.594
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    7.373
_exptl_absorpt_correction_T_max  0.761
_exptl_absorpt_correction_T_min  0.179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.040
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.681
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1198
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0333
_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)+(0.0360P)²+0.8623P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0827
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1076
_reflns_number_total             1198
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8dt04820g2.cif
_cod_data_source_block           wa1973
_cod_depositor_comments
'Adding full bibliography for 7048415--7048428.cif.'
_cod_database_code               7048417
_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   0.208
_shelx_estimated_absorpt_t_max   0.557
_shelxl_version_number           2014-1
_shelx_res_file
; 
TITL wa1973 in C2/c 
CELL 0.71073  18.001    9.0764   7.2612  90.000 112.754  90.000 
ZERR    4.00   0.002    0.0006   0.0009   0.000   0.009   0.000 
LATT  7 
SYMM -X, Y, 0.5-Z 
SFAC C H BR 
UNIT 56 32 8 
TEMP-100 
SIZE.31 .09 .09 
REM colourless needle 
ACTA50 
CONF 
L.S.10 
BOND$H 
FMAP 2 
PLAN 10 
WGHT    0.036000    0.862300 
FVAR       0.11698 
BR1   3    0.093667    0.110239    0.409951    11.00000    0.03848    0.01927 = 
         0.03826    0.00481    0.00361    0.00948 
C1    1    0.082544    0.424966    0.389762    11.00000    0.01657    0.02025 = 
         0.01601    0.00091    0.00772    0.00082 
C2    1    0.041551    0.559866    0.320816    11.00000    0.01804    0.01958 = 
         0.01670   -0.00083    0.00872    0.00001 
C3    1    0.083509    0.692767    0.395299    11.00000    0.02640    0.02319 = 
         0.02847   -0.00323    0.01170   -0.00568 
AFIX  43 
H3    2    0.056889    0.784413    0.352735    11.00000   -1.20000 
AFIX   0 
C4    1    0.162552    0.690697    0.528887    11.00000    0.02792    0.03089 = 
         0.02959   -0.00804    0.01455   -0.01205 
AFIX  43 
H4    2    0.189972    0.780962    0.576559    11.00000   -1.20000 
AFIX   0 
C5    1    0.202834    0.557373    0.595031    11.00000    0.01764    0.04449 = 
         0.02156   -0.00379    0.00549   -0.00796 
AFIX  43 
H5    2    0.257244    0.557192    0.687758    11.00000   -1.20000 
AFIX   0 
C6    1    0.163716    0.426838    0.525905    11.00000    0.01907    0.02951 = 
         0.02073    0.00159    0.00733    0.00119 
AFIX  43 
H6    2    0.191545    0.336461    0.570112    11.00000   -1.20000 
AFIX   0 
C7    1    0.038999    0.290042    0.315987    11.00000    0.02309    0.01322 = 
         0.01815    0.00127    0.00762    0.00208 
HKLF 4 
  
REM  wa1973 in C2/c 
REM R1 =  0.0333 for    1076 Fo > 4sig(Fo)  and  0.0385 for all    1198 data 
REM     73 parameters refined using      0 restraints 
  
END 
  
WGHT      0.0360      0.8621 
  
REM Highest difference peak  0.588,  deepest hole -0.681,  1-sigma level  0.112 
Q1    1   0.1355  0.1139  0.3036  11.00000  0.05    0.59 
Q2    1   0.1597  0.1018  0.5770  11.00000  0.05    0.49 
Q3    1   0.0671  0.1076  0.5412  11.00000  0.05    0.46 
Q4    1   0.0000  0.1031  0.2500  10.50000  0.05    0.43 
Q5    1   0.0602  0.2192  0.4405  11.00000  0.05    0.35 
Q6    1   0.1619  0.7859  0.6789  11.00000  0.05    0.32 
Q7    1   0.0369  0.7903  0.1594  11.00000  0.05    0.30 
Q8    1   0.0804  0.0187  0.2296  11.00000  0.05    0.30 
Q9    1   0.1501  0.6788  0.6848  11.00000  0.05    0.29 
Q10   1   0.0682 -0.0017  0.4596  11.00000  0.05    0.29 
;
_shelx_res_checksum              63300
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
Br1 Br 0.09367(2) 0.11024(3) 0.40995(5) 0.03540(15) Uani 1 1 d . .
C1 C 0.08254(15) 0.4250(3) 0.3898(4) 0.0172(5) Uani 1 1 d . .
C2 C 0.04155(14) 0.5599(3) 0.3208(3) 0.0175(5) Uani 1 1 d . .
C3 C 0.08351(17) 0.6928(3) 0.3953(4) 0.0257(6) Uani 1 1 d . .
H3 H 0.0569 0.7844 0.3527 0.031 Uiso 1 1 calc R U
C4 C 0.16255(17) 0.6907(4) 0.5289(4) 0.0284(6) Uani 1 1 d . .
H4 H 0.1900 0.7810 0.5766 0.034 Uiso 1 1 calc R U
C5 C 0.20283(17) 0.5574(4) 0.5950(4) 0.0285(6) Uani 1 1 d . .
H5 H 0.2572 0.5572 0.6878 0.034 Uiso 1 1 calc R U
C6 C 0.16372(16) 0.4268(3) 0.5259(4) 0.0232(5) Uani 1 1 d . .
H6 H 0.1915 0.3365 0.5701 0.028 Uiso 1 1 calc R U
C7 C 0.03900(15) 0.2900(3) 0.3160(3) 0.0183(5) Uani 1 1 d . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0385(2) 0.0193(2) 0.0383(2) 0.00481(11) 0.00361(16) 0.00948(11)
C1 0.0166(11) 0.0202(12) 0.0160(11) 0.0009(9) 0.0077(9) 0.0008(9)
C2 0.0180(12) 0.0196(12) 0.0167(11) -0.0008(9) 0.0087(10) 0.0000(10)
C3 0.0264(13) 0.0232(15) 0.0285(14) -0.0032(11) 0.0117(12) -0.0057(11)
C4 0.0279(14) 0.0309(15) 0.0296(14) -0.0080(12) 0.0145(12) -0.0121(12)
C5 0.0176(12) 0.0445(18) 0.0216(13) -0.0038(12) 0.0055(10) -0.0080(12)
C6 0.0191(12) 0.0295(14) 0.0207(12) 0.0016(10) 0.0073(10) 0.0012(11)
C7 0.0231(13) 0.0132(11) 0.0182(12) 0.0013(9) 0.0076(10) 0.0021(9)
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'
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
C6 C1 C2 119.5(2) . .
C6 C1 C7 122.5(3) . .
C2 C1 C7 118.0(2) . .
C3 C2 C1 118.3(2) . .
C3 C2 C2 121.50(16) . 2
C1 C2 C2 120.24(15) . 2
C4 C3 C2 120.7(3) . .
C4 C3 H3 119.6 . .
C2 C3 H3 119.6 . .
C3 C4 C5 120.7(3) . .
C3 C4 H4 119.6 . .
C5 C4 H4 119.6 . .
C6 C5 C4 119.9(3) . .
C6 C5 H5 120.1 . .
C4 C5 H5 120.1 . .
C5 C6 C1 120.8(3) . .
C5 C6 H6 119.6 . .
C1 C6 H6 119.6 . .
C7 C7 C1 121.80(15) 2 .
C7 C7 Br1 120.37(8) 2 .
C1 C7 Br1 117.83(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C7 1.892(2) .
C1 C6 1.413(3) .
C1 C2 1.417(4) .
C1 C7 1.441(4) .
C2 C3 1.415(4) .
C2 C2 1.451(5) 2
C3 C4 1.378(4) .
C3 H3 0.9500 .
C4 C5 1.397(5) .
C4 H4 0.9500 .
C5 C6 1.370(4) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 C7 1.360(5) 2
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_4
C6 C1 C2 C3 -1.4(3) . .
C7 C1 C2 C3 178.9(2) . .
C6 C1 C2 C2 179.3(3) . 2
C7 C1 C2 C2 -0.4(4) . 2
C1 C2 C3 C4 1.0(4) . .
C2 C2 C3 C4 -179.6(3) 2 .
C2 C3 C4 C5 -0.5(4) . .
C3 C4 C5 C6 0.4(4) . .
C4 C5 C6 C1 -0.7(4) . .
C2 C1 C6 C5 1.2(4) . .
C7 C1 C6 C5 -179.1(2) . .
C6 C1 C7 C7 -179.6(3) . 2
C2 C1 C7 C7 0.1(4) . 2
C6 C1 C7 Br1 0.8(3) . .
C2 C1 C7 Br1 -179.52(17) . .
