#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:55:00 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180202 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/96/7109626.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_7109626
loop_
_publ_author_name
'Parantap Sarkar'
'Fabien Durola'
'Harald Bock'
_publ_section_title
;
 Dipyreno- and diperyleno-anthracenes from glyoxylic Perkin reactions
;
_journal_coden_Cambridge         0182
_journal_name_full               Chem.Commun.
_journal_page_first              7552
_journal_paper_doi               10.1039/c3cc44044c
_journal_volume                  49
_journal_year                    2013
_chemical_formula_moiety         'C54 H40 Br2 O8'
_chemical_formula_sum            'C54 H40 Br2 O8'
_chemical_formula_weight         976.68
_chemical_name_common
2,5-dibromo-1,4-phenylenebis((1-pyrenyl)maleate)
_chemical_name_systematic
; 
 ? 
;
_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                 116.317(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.9924(5)
_cell_length_b                   17.9529(10)
_cell_length_c                   15.1993(8)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.12
_cell_measurement_theta_min      2.27
_cell_volume                     2199.4(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  'WINGX (Farrugia)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0570
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            117994
_diffrn_reflns_theta_full        30.11
_diffrn_reflns_theta_max         30.11
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    1.901
_exptl_absorpt_correction_T_max  0.9109
_exptl_absorpt_correction_T_min  0.5023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             996
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         6445
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0327P)²+2.3116P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0914
_reflns_number_gt                4333
_reflns_number_total             6445
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc44044c.txt
_cod_data_source_block           global
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' 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      P2(1)/c
_cod_database_code               7109626
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
Br1 Br -0.76774(3) 0.000693(13) 0.090741(17) 0.02491(7) Uani 1 1 d .
O1 O -0.4586(2) -0.30234(9) 0.15741(15) 0.0404(4) Uani 1 1 d .
O2 O -0.4217(2) -0.23707(10) 0.29225(13) 0.0423(5) Uani 1 1 d .
O3 O -0.79748(17) -0.14831(8) -0.04235(11) 0.0219(3) Uani 1 1 d .
O4 O -0.76071(19) -0.20909(9) 0.09510(11) 0.0274(3) Uani 1 1 d .
C1 C -0.0386(4) 0.11860(16) 0.44399(19) 0.0417(6) Uani 1 1 d .
H1 H -0.1140 0.1458 0.4575 0.050 Uiso 1 1 calc R
C2 C 0.1238(4) 0.14258(17) 0.4807(2) 0.0477(7) Uani 1 1 d .
H2 H 0.1568 0.1854 0.5190 0.057 Uiso 1 1 calc R
C3 C 0.2376(4) 0.10317(17) 0.46076(19) 0.0459(7) Uani 1 1 d .
H3 H 0.3462 0.1203 0.4856 0.055 Uiso 1 1 calc R
C4 C 0.1933(3) 0.03818(16) 0.40430(18) 0.0357(6) Uani 1 1 d .
C5 C 0.3070(3) -0.00411(16) 0.38165(19) 0.0399(6) Uani 1 1 d .
H5 H 0.4162 0.0121 0.4052 0.048 Uiso 1 1 calc R
C6 C 0.2604(3) -0.06651(16) 0.32731(19) 0.0365(6) Uani 1 1 d .
H6 H 0.3384 -0.0927 0.3149 0.044 Uiso 1 1 calc R
C7 C 0.0921(3) -0.09395(14) 0.28776(17) 0.0282(5) Uani 1 1 d .
C8 C -0.0251(3) -0.05286(13) 0.30797(16) 0.0237(5) Uani 1 1 d .
C9 C 0.0252(3) 0.01280(13) 0.36656(17) 0.0287(5) Uani 1 1 d .
C10 C -0.0917(3) 0.05374(14) 0.38653(17) 0.0306(5) Uani 1 1 d .
C11 C -0.2587(3) 0.02773(15) 0.34699(18) 0.0313(5) Uani 1 1 d .
H11 H -0.3358 0.0540 0.3601 0.038 Uiso 1 1 calc R
C12 C -0.3076(3) -0.03446(13) 0.29081(17) 0.0267(5) Uani 1 1 d .
H12 H -0.4176 -0.0497 0.2658 0.032 Uiso 1 1 calc R
C13 C -0.1931(3) -0.07739(12) 0.26893(15) 0.0214(4) Uani 1 1 d .
C14 C -0.2394(2) -0.14242(12) 0.21099(16) 0.0218(4) Uani 1 1 d .
C15 C -0.1216(3) -0.18270(13) 0.19398(17) 0.0264(5) Uani 1 1 d .
H15 H -0.1526 -0.2265 0.1576 0.032 Uiso 1 1 calc R
C16 C 0.0415(3) -0.15784(14) 0.23095(18) 0.0308(5) Uani 1 1 d .
H16 H 0.1176 -0.1845 0.2173 0.037 Uiso 1 1 calc R
C17 C -0.4138(3) -0.16987(12) 0.16419(16) 0.0214(4) Uani 1 1 d .
C18 C -0.4380(3) -0.24466(13) 0.20155(18) 0.0282(5) Uani 1 1 d .
C19 C -0.4482(4) -0.30373(18) 0.3380(2) 0.0513(8) Uani 1 1 d .
H19A H -0.3835 -0.3005 0.4087 0.062 Uiso 1 1 calc R
H19B H -0.4110 -0.3471 0.3153 0.062 Uiso 1 1 calc R
C20 C -0.6242(3) -0.31198(16) 0.3139(2) 0.0434(7) Uani 1 1 d .
H20A H -0.6578 -0.2718 0.3427 0.065 Uiso 1 1 calc R
H20B H -0.6411 -0.3585 0.3393 0.065 Uiso 1 1 calc R
H20C H -0.6890 -0.3111 0.2439 0.065 Uiso 1 1 calc R
C21 C -0.5405(2) -0.13475(11) 0.09260(16) 0.0194(4) Uani 1 1 d .
C22 C -0.7108(3) -0.16870(11) 0.05091(16) 0.0198(4) Uani 1 1 d .
C23 C -0.9686(3) -0.17379(13) -0.09243(16) 0.0254(5) Uani 1 1 d .
H23A H -1.0290 -0.1604 -0.0553 0.031 Uiso 1 1 calc R
H23B H -0.9730 -0.2274 -0.1008 0.031 Uiso 1 1 calc R
C24 C -1.0414(3) -0.13523(14) -0.19054(17) 0.0276(5) Uani 1 1 d .
H24A H -1.0306 -0.0823 -0.1809 0.041 Uiso 1 1 calc R
H24B H -1.1567 -0.1480 -0.2260 0.041 Uiso 1 1 calc R
H24C H -0.9834 -0.1508 -0.2273 0.041 Uiso 1 1 calc R
C25 C -0.5184(2) -0.06503(11) 0.04734(15) 0.0172(4) Uani 1 1 d .
C26 C -0.5974(2) 0.06184(11) -0.00977(15) 0.0176(4) Uani 1 1 d .
H26 H -0.6642 0.1030 -0.0160 0.021 Uiso 1 1 calc R
C27 C -0.6146(2) -0.00131(11) 0.03649(14) 0.0170(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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C18 O2 C19 116.5(2) . .
C22 O3 C23 117.06(16) . .
C2 C1 C10 121.1(3) . .
C2 C1 H1 119.5 . .
C10 C1 H1 119.5 . .
C1 C2 C3 120.3(3) . .
C1 C2 H2 119.9 . .
C3 C2 H2 119.9 . .
C2 C3 C4 121.6(3) . .
C2 C3 H3 119.2 . .
C4 C3 H3 119.2 . .
C3 C4 C9 118.3(3) . .
C3 C4 C5 123.4(2) . .
C9 C4 C5 118.3(2) . .
C6 C5 C4 121.9(2) . .
C6 C5 H5 119.1 . .
C4 C5 H5 119.1 . .
C5 C6 C7 121.6(2) . .
C5 C6 H6 119.2 . .
C7 C6 H6 119.2 . .
C16 C7 C8 119.5(2) . .
C16 C7 C6 122.4(2) . .
C8 C7 C6 118.1(2) . .
C9 C8 C13 120.0(2) . .
C9 C8 C7 120.1(2) . .
C13 C8 C7 119.9(2) . .
C10 C9 C8 120.1(2) . .
C10 C9 C4 119.9(2) . .
C8 C9 C4 120.0(2) . .
C1 C10 C9 118.8(2) . .
C1 C10 C11 122.5(2) . .
C9 C10 C11 118.8(2) . .
C12 C11 C10 121.5(2) . .
C12 C11 H11 119.3 . .
C10 C11 H11 119.3 . .
C11 C12 C13 121.4(2) . .
C11 C12 H12 119.3 . .
C13 C12 H12 119.3 . .
C14 C13 C8 118.72(19) . .
C14 C13 C12 123.02(19) . .
C8 C13 C12 118.3(2) . .
C15 C14 C13 120.40(19) . .
C15 C14 C17 117.7(2) . .
C13 C14 C17 121.93(19) . .
C16 C15 C14 120.6(2) . .
C16 C15 H15 119.7 . .
C14 C15 H15 119.7 . .
C7 C16 C15 120.9(2) . .
C7 C16 H16 119.5 . .
C15 C16 H16 119.5 . .
C21 C17 C14 124.78(19) . .
C21 C17 C18 120.91(19) . .
C14 C17 C18 114.26(18) . .
O1 C18 O2 125.9(2) . .
O1 C18 C17 124.6(2) . .
O2 C18 C17 109.3(2) . .
O2 C19 C20 110.6(2) . .
O2 C19 H19A 109.5 . .
C20 C19 H19A 109.5 . .
O2 C19 H19B 109.5 . .
C20 C19 H19B 109.5 . .
H19A C19 H19B 108.1 . .
C19 C20 H20A 109.5 . .
C19 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C19 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C17 C21 C25 122.39(18) . .
C17 C21 C22 119.62(18) . .
C25 C21 C22 117.87(17) . .
O4 C22 O3 124.97(19) . .
O4 C22 C21 124.9(2) . .
O3 C22 C21 110.12(17) . .
O3 C23 C24 105.55(17) . .
O3 C23 H23A 110.6 . .
C24 C23 H23A 110.6 . .
O3 C23 H23B 110.6 . .
C24 C23 H23B 110.6 . .
H23A C23 H23B 108.8 . .
C23 C24 H24A 109.5 . .
C23 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
C23 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
C26 C25 C27 116.97(17) 3_455 .
C26 C25 C21 120.18(17) 3_455 .
C27 C25 C21 122.81(18) . .
C27 C26 C25 121.09(18) . 3_455
C27 C26 H26 119.5 . .
C25 C26 H26 119.5 3_455 .
C26 C27 C25 121.94(17) . .
C26 C27 Br1 118.33(15) . .
C25 C27 Br1 119.68(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C27 1.8930(18) .
O1 C18 1.203(3) .
O2 C18 1.327(3) .
O2 C19 1.456(3) .
O3 C22 1.331(3) .
O3 C23 1.456(2) .
O4 C22 1.203(2) .
C1 C2 1.380(4) .
C1 C10 1.406(4) .
C1 H1 0.9300 .
C2 C3 1.383(4) .
C2 H2 0.9300 .
C3 C4 1.397(4) .
C3 H3 0.9300 .
C4 C9 1.432(3) .
C4 C5 1.433(4) .
C5 C6 1.344(4) .
C5 H5 0.9300 .
C6 C7 1.445(3) .
C6 H6 0.9300 .
C7 C16 1.386(4) .
C7 C8 1.427(3) .
C8 C9 1.425(3) .
C8 C13 1.426(3) .
C9 C10 1.421(3) .
C10 C11 1.427(3) .
C11 C12 1.355(4) .
C11 H11 0.9300 .
C12 C13 1.438(3) .
C12 H12 0.9300 .
C13 C14 1.410(3) .
C14 C15 1.398(3) .
C14 C17 1.490(3) .
C15 C16 1.391(3) .
C15 H15 0.9300 .
C16 H16 0.9300 .
C17 C21 1.334(3) .
C17 C18 1.510(3) .
C19 C20 1.465(4) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C21 C25 1.483(3) .
C21 C22 1.502(3) .
C23 C24 1.505(3) .
C23 H23A 0.9700 .
C23 H23B 0.9700 .
C24 H24A 0.9600 .
C24 H24B 0.9600 .
C24 H24C 0.9600 .
C25 C26 1.393(3) 3_455
C25 C27 1.399(3) .
C26 C27 1.379(3) .
C26 C25 1.393(3) 3_455
C26 H26 0.9300 .
