#------------------------------------------------------------------------------
#$Date: 2021-12-07 05:49:59 +0200 (Tue, 07 Dec 2021) $
#$Revision: 271207 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158369.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_7158369
loop_
_publ_author_name
'Islam, Khadimul'
'Narjinari, Himani'
'Bisarya, Akshara'
'Kumar, Akshai'
_publ_section_title
;
 Multi-fold Sonogashira coupling: a new and convenient approach to obtain
 tetraalkynyl anthracenes with tunable photophysical properties.
;
_journal_issue                   44
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9692
_journal_page_last               9704
_journal_paper_doi               10.1039/d1ob01861b
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C32 H18'
_chemical_formula_sum            'C32 H18'
_chemical_formula_weight         402.46
_chemical_name_common            1,4-di(anthracen-9-yl)buta-1,3-diyne
_chemical_name_systematic        1,4-di(anthracen-9-yl)buta-1,3-diyne
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2021-05-29 deposited with the CCDC.	2021-10-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.162(3)
_cell_length_b                   11.978(3)
_cell_length_c                   15.916(4)
_cell_measurement_reflns_used    3065
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.49
_cell_volume                     2127.9(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.815
_diffrn_measured_fraction_theta_max 0.815
_diffrn_measurement_device_type  'CCD area detector'
_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  0.1000
_diffrn_reflns_av_sigmaI/netI    0.1338
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12932
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.49
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             924
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane + Dichloromethane'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.790
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3065
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.790
_refine_ls_R_factor_all          0.1641
_refine_ls_R_factor_gt           0.0719
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1959P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2009
_refine_ls_wR_factor_ref         0.2674
_reflns_number_gt                1427
_reflns_number_total             3065
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1ob01861b2.cif
_cod_data_source_block           adkhdann_0ma_a
_cod_depositor_comments
'Adding full bibliography for 7158365--7158370.cif.'
_cod_original_cell_volume        2128.0(9)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7158369
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C001 C 0.3177(3) 0.7265(3) 0.2604(2) 0.0508(9) Uani 1 1 d . . .
C002 C 0.2775(3) 0.5956(3) 0.37509(19) 0.0485(8) Uani 1 1 d . . .
C003 C 0.3512(3) 0.6308(2) 0.30799(19) 0.0473(8) Uani 1 1 d . . .
C004 C 0.1709(3) 0.6535(3) 0.3946(2) 0.0500(8) Uani 1 1 d . . .
C005 C 0.3105(3) 0.5014(3) 0.4234(2) 0.0571(9) Uani 1 1 d . . .
C006 C 0.4065(3) 0.2576(3) 0.5528(2) 0.0637(11) Uani 1 1 d . . .
C007 C 0.4590(3) 0.5752(3) 0.2861(2) 0.0575(9) Uani 1 1 d . . .
H007 H 0.4839 0.5140 0.3174 0.069 Uiso 1 1 calc R . .
C008 C 0.3394(3) 0.4218(3) 0.4647(2) 0.0630(10) Uani 1 1 d . . .
C009 C 0.1397(3) 0.7495(3) 0.3462(2) 0.0546(9) Uani 1 1 d . . .
C00A C 0.2131(3) 0.7836(3) 0.2813(2) 0.0583(10) Uani 1 1 d . . .
H00A H 0.1921 0.8466 0.2505 0.070 Uiso 1 1 calc R . .
C00B C 0.0925(3) 0.6190(3) 0.4599(2) 0.0622(10) Uani 1 1 d . . .
H00B H 0.1125 0.5574 0.4927 0.075 Uiso 1 1 calc R . .
C00C C 0.4554(4) 0.1640(3) 0.5956(3) 0.0669(11) Uani 1 1 d . . .
C00D C 0.3921(4) 0.7592(3) 0.1926(2) 0.0640(10) Uani 1 1 d . . .
H00D H 0.3705 0.8210 0.1607 0.077 Uiso 1 1 calc R . .
C00E C 0.0311(4) 0.8062(3) 0.3665(3) 0.0687(11) Uani 1 1 d . . .
H00E H 0.0096 0.8698 0.3366 0.082 Uiso 1 1 calc R . .
C00F C 0.4927(4) 0.7039(3) 0.1731(2) 0.0691(11) Uani 1 1 d . . .
H00F H 0.5401 0.7276 0.1284 0.083 Uiso 1 1 calc R . .
C00G C -0.0109(4) 0.6747(4) 0.4750(3) 0.0722(11) Uani 1 1 d . . .
H00G H -0.0624 0.6497 0.5170 0.087 Uiso 1 1 calc R . .
C00H C 0.5261(3) 0.6101(3) 0.2202(2) 0.0673(10) Uani 1 1 d . . .
H00H H 0.5953 0.5712 0.2060 0.081 Uiso 1 1 calc R . .
C00I C 0.3738(4) 0.3326(4) 0.5109(3) 0.0738(12) Uani 1 1 d . . .
C00J C 0.4008(4) 0.1225(3) 0.6676(3) 0.0717(12) Uani 1 1 d . . .
C00K C 0.5641(4) 0.1161(3) 0.5632(3) 0.0751(13) Uani 1 1 d . . .
C00L C -0.0411(4) 0.7687(4) 0.4286(3) 0.0771(13) Uani 1 1 d . . .
H00L H -0.1119 0.8065 0.4405 0.092 Uiso 1 1 calc R . .
C00M C 0.2952(7) 0.0343(6) 0.8123(4) 0.128(3) Uani 1 1 d . . .
H00M H 0.2598 0.0038 0.8599 0.154 Uiso 1 1 calc R . .
C00N C 0.2977(5) 0.1705(4) 0.7017(3) 0.0920(16) Uani 1 1 d . . .
H00N H 0.2650 0.2325 0.6750 0.110 Uiso 1 1 calc R . .
C00O C 0.5583(6) -0.0170(4) 0.6745(4) 0.107(2) Uani 1 1 d . . .
H00O H 0.5917 -0.0791 0.7005 0.128 Uiso 1 1 calc R . .
C00P C 0.4517(6) 0.0271(4) 0.7088(3) 0.0942(17) Uani 1 1 d . . .
C00Q C 0.6155(5) 0.0254(4) 0.6060(4) 0.0948(17) Uani 1 1 d . . .
C00R C 0.6231(4) 0.1584(4) 0.4924(3) 0.0891(14) Uani 1 1 d . . .
H00R H 0.5902 0.2189 0.4639 0.107 Uiso 1 1 calc R . .
C00S C 0.2420(5) 0.1309(5) 0.7727(4) 0.123(2) Uani 1 1 d . . .
H00S H 0.1735 0.1645 0.7942 0.148 Uiso 1 1 calc R . .
C00T C 0.7269(6) -0.0204(5) 0.5732(5) 0.120(2) Uani 1 1 d . . .
H00T H 0.7614 -0.0819 0.5993 0.143 Uiso 1 1 calc R . .
C00U C 0.3940(8) -0.0111(6) 0.7813(4) 0.137(3) Uani 1 1 d . . .
H00U H 0.4269 -0.0718 0.8095 0.164 Uiso 1 1 calc R . .
C00V C 0.7800(7) 0.0244(7) 0.5062(6) 0.133(2) Uani 1 1 d . . .
H00V H 0.8529 -0.0039 0.4875 0.160 Uiso 1 1 calc R . .
C00W C 0.7269(5) 0.1131(5) 0.4644(4) 0.117(2) Uani 1 1 d . . .
H00W H 0.7631 0.1420 0.4165 0.140 Uiso 1 1 calc R . .
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'
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
C00A C001 C00D 122.5(3) . . ?
C00A C001 C003 119.3(3) . . ?
C00D C001 C003 118.3(3) . . ?
C004 C002 C003 120.7(3) . . ?
C004 C002 C005 119.5(3) . . ?
C003 C002 C005 119.8(3) . . ?
C002 C003 C007 122.7(3) . . ?
C002 C003 C001 119.3(3) . . ?
C007 C003 C001 118.1(3) . . ?
C002 C004 C00B 122.4(3) . . ?
C002 C004 C009 118.9(3) . . ?
C00B C004 C009 118.6(3) . . ?
C008 C005 C002 179.5(4) . . ?
C00I C006 C00C 173.2(4) . . ?
C00H C007 C003 121.0(3) . . ?
C00H C007 H007 119.5 . . ?
C003 C007 H007 119.5 . . ?
C005 C008 C00I 179.0(4) . . ?
C00A C009 C004 119.8(3) . . ?
C00A C009 C00E 122.2(3) . . ?
C004 C009 C00E 118.0(3) . . ?
C009 C00A C001 122.1(3) . . ?
C009 C00A H00A 119.0 . . ?
C001 C00A H00A 119.0 . . ?
C00G C00B C004 120.7(4) . . ?
C00G C00B H00B 119.6 . . ?
C004 C00B H00B 119.6 . . ?
C00J C00C C006 120.6(4) . . ?
C00J C00C C00K 121.5(4) . . ?
C006 C00C C00K 117.9(4) . . ?
C00F C00D C001 122.1(3) . . ?
C00F C00D H00D 119.0 . . ?
C001 C00D H00D 119.0 . . ?
C00L C00E C009 120.9(4) . . ?
C00L C00E H00E 119.6 . . ?
C009 C00E H00E 119.6 . . ?
C00D C00F C00H 119.7(3) . . ?
C00D C00F H00F 120.2 . . ?
C00H C00F H00F 120.2 . . ?
C00B C00G C00L 120.8(4) . . ?
C00B C00G H00G 119.6 . . ?
C00L C00G H00G 119.6 . . ?
C007 C00H C00F 121.0(3) . . ?
C007 C00H H00H 119.5 . . ?
C00F C00H H00H 119.5 . . ?
C006 C00I C008 177.6(5) . . ?
C00C C00J C00N 122.3(4) . . ?
C00C C00J C00P 119.2(5) . . ?
C00N C00J C00P 118.5(4) . . ?
C00R C00K C00Q 118.6(5) . . ?
C00R C00K C00C 122.7(4) . . ?
C00Q C00K C00C 118.6(5) . . ?
C00E C00L C00G 121.0(4) . . ?
C00E C00L H00L 119.5 . . ?
C00G C00L H00L 119.5 . . ?
C00U C00M C00S 120.6(6) . . ?
C00U C00M H00M 119.7 . . ?
C00S C00M H00M 119.7 . . ?
C00S C00N C00J 123.4(5) . . ?
C00S C00N H00N 118.3 . . ?
C00J C00N H00N 118.3 . . ?
C00Q C00O C00P 124.4(5) . . ?
C00Q C00O H00O 117.8 . . ?
C00P C00O H00O 117.8 . . ?
C00U C00P C00O 125.8(6) . . ?
C00U C00P C00J 117.1(7) . . ?
C00O C00P C00J 117.1(5) . . ?
C00O C00Q C00K 119.0(6) . . ?
C00O C00Q C00T 123.2(6) . . ?
C00K C00Q C00T 117.7(6) . . ?
C00W C00R C00K 121.5(6) . . ?
C00W C00R H00R 119.3 . . ?
C00K C00R H00R 119.3 . . ?
C00N C00S C00M 116.7(6) . . ?
C00N C00S H00S 121.7 . . ?
C00M C00S H00S 121.7 . . ?
C00V C00T C00Q 121.1(6) . . ?
C00V C00T H00T 119.5 . . ?
C00Q C00T H00T 119.5 . . ?
C00M C00U C00P 123.8(7) . . ?
C00M C00U H00U 118.1 . . ?
C00P C00U H00U 118.1 . . ?
C00T C00V C00W 120.1(7) . . ?
C00T C00V H00V 119.9 . . ?
C00W C00V H00V 119.9 . . ?
C00R C00W C00V 121.0(7) . . ?
C00R C00W H00W 119.5 . . ?
C00V C00W H00W 119.5 . . ?
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
C001 C00A 1.393(5) . ?
C001 C00D 1.417(5) . ?
C001 C003 1.424(4) . ?
C002 C004 1.412(5) . ?
C002 C003 1.413(5) . ?
C002 C005 1.414(5) . ?
C003 C007 1.418(5) . ?
C004 C00B 1.421(5) . ?
C004 C009 1.426(5) . ?
C005 C008 1.202(5) . ?
C006 C00I 1.177(5) . ?
C006 C00C 1.420(5) . ?
C007 C00H 1.355(5) . ?
C007 H007 0.9300 . ?
C008 C00I 1.353(5) . ?
C009 C00A 1.381(5) . ?
C009 C00E 1.427(5) . ?
C00A H00A 0.9300 . ?
C00B C00G 1.356(5) . ?
C00B H00B 0.9300 . ?
C00C C00J 1.390(6) . ?
C00C C00K 1.438(6) . ?
C00D C00F 1.341(5) . ?
C00D H00D 0.9300 . ?
C00E C00L 1.352(6) . ?
C00E H00E 0.9300 . ?
C00F C00H 1.401(5) . ?
C00F H00F 0.9300 . ?
C00G C00L 1.388(6) . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9300 . ?
C00J C00N 1.396(7) . ?
C00J C00P 1.434(6) . ?
C00K C00R 1.400(7) . ?
C00K C00Q 1.405(6) . ?
C00L H00L 0.9300 . ?
C00M C00U 1.324(11) . ?
C00M C00S 1.445(9) . ?
C00M H00M 0.9300 . ?
C00N C00S 1.374(7) . ?
C00N H00N 0.9300 . ?
C00O C00Q 1.361(8) . ?
C00O C00P 1.412(8) . ?
C00O H00O 0.9300 . ?
C00P C00U 1.399(9) . ?
C00Q C00T 1.456(9) . ?
C00R C00W 1.355(7) . ?
C00R H00R 0.9300 . ?
C00S H00S 0.9300 . ?
C00T C00V 1.332(9) . ?
C00T H00T 0.9300 . ?
C00U H00U 0.9300 . ?
C00V C00W 1.387(9) . ?
C00V H00V 0.9300 . ?
C00W H00W 0.9300 . ?
