#------------------------------------------------------------------------------
#$Date: 2019-11-28 16:34:53 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244113 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/55/7125594.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_7125594
loop_
_publ_author_name
'Kulisic, Niksa'
'More, Sandeep'
'Mateo-Alonso, Aurelio'
_publ_section_title
;
 A tetraalkylated pyrene building block for the synthesis of pyrene-fused
 azaacenes with enhanced solubility.
;
_journal_issue                   1
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              514
_journal_page_last               516
_journal_paper_doi               10.1039/c0cc02249g
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C48 H58'
_chemical_formula_weight         634.94
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.641(4)
_cell_angle_beta                 109.323(6)
_cell_angle_gamma                96.475(7)
_cell_formula_units_Z            1
_cell_length_a                   8.4918(6)
_cell_length_b                   9.8418(13)
_cell_length_c                   12.6119(14)
_cell_measurement_reflns_used    6390
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     955.64(19)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'long-fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_sigmaI/netI    0.1066
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9010
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.103
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             346
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3901
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.924
_refine_ls_R_factor_all          0.1383
_refine_ls_R_factor_gt           0.0537
_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)+(0.0604P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1439
_reflns_number_gt                1876
_reflns_number_total             3901
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0cc02249g.txt
_cod_data_source_block           jg065a
_cod_original_cell_volume        955.64(18)
_cod_database_code               7125594
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.2292(2) 0.8240(2) 0.69875(16) 0.0247(5) Uani 1 1 d .
H1 H 0.2901 0.7752 0.7518 0.030 Uiso 1 1 calc R
C2 C 0.0936(2) 0.8803(2) 0.71603(16) 0.0246(5) Uani 1 1 d .
C3 C 0.0008(2) 0.9520(2) 0.63745(16) 0.0226(5) Uani 1 1 d .
C4 C 0.0474(2) 0.9657(2) 0.54087(15) 0.0213(5) Uani 1 1 d .
C5 C 0.1880(2) 0.9090(2) 0.52541(16) 0.0218(5) Uani 1 1 d .
C6 C 0.2774(2) 0.8377(2) 0.60549(16) 0.0235(5) Uani 1 1 d .
C7 C -0.1420(2) 1.0094(2) 0.64927(16) 0.0257(5) Uani 1 1 d .
H7 H -0.1743 1.0012 0.7133 0.031 Uiso 1 1 calc R
C8 C 0.2313(2) 0.9255(2) 0.42773(16) 0.0256(5) Uani 1 1 d .
H8 H 0.3257 0.8895 0.4171 0.031 Uiso 1 1 calc R
C9 C 0.0432(2) 0.8565(2) 0.81012(17) 0.0301(5) Uani 1 1 d .
C10 C -0.0039(2) 0.8312(2) 0.88512(18) 0.0334(5) Uani 1 1 d .
C11 C -0.0702(2) 0.7998(3) 0.97295(17) 0.0365(6) Uani 1 1 d .
H11A H -0.0127 0.8747 1.0462 0.044 Uiso 1 1 calc R
H11B H -0.0421 0.7091 0.9885 0.044 Uiso 1 1 calc R
C12 C -0.2611(3) 0.7901(3) 0.93692(19) 0.0441(6) Uani 1 1 d .
H12A H -0.3187 0.7149 0.8639 0.053 Uiso 1 1 calc R
H12B H -0.2894 0.8807 0.9212 0.053 Uiso 1 1 calc R
C13 C -0.3283(2) 0.7580(3) 1.02872(18) 0.0407(6) Uani 1 1 d .
H13A H -0.2949 0.6698 1.0470 0.049 Uiso 1 1 calc R
H13B H -0.2739 0.8354 1.1006 0.049 Uiso 1 1 calc R
C14 C -0.5201(3) 0.7414(3) 0.99244(19) 0.0504(7) Uani 1 1 d .
H14A H -0.5739 0.6652 0.9197 0.060 Uiso 1 1 calc R
H14B H -0.5528 0.8302 0.9752 0.060 Uiso 1 1 calc R
C15 C -0.5911(3) 0.7069(3) 1.08213(19) 0.0498(7) Uani 1 1 d .
H15A H -0.7166 0.6802 1.0456 0.060 Uiso 1 1 calc R
H15B H -0.5482 0.6242 1.1061 0.060 Uiso 1 1 calc R
C16 C -0.5446(3) 0.8279(3) 1.1889(2) 0.0560(8) Uani 1 1 d .
H16A H -0.5929 0.7986 1.2433 0.084 Uiso 1 1 calc R
H16B H -0.5902 0.9092 1.1664 0.084 Uiso 1 1 calc R
H16C H -0.4205 0.8543 1.2264 0.084 Uiso 1 1 calc R
C17 C 0.4144(2) 0.7734(2) 0.58956(16) 0.0280(5) Uani 1 1 d .
C18 C 0.5268(2) 0.7177(2) 0.57565(17) 0.0297(5) Uani 1 1 d .
C19 C 0.6640(2) 0.6516(2) 0.55508(16) 0.0286(5) Uani 1 1 d .
H19A H 0.6435 0.5515 0.5577 0.034 Uiso 1 1 calc R
H19B H 0.7732 0.6998 0.6184 0.034 Uiso 1 1 calc R
C20 C 0.6789(2) 0.6576(2) 0.43883(16) 0.0288(5) Uani 1 1 d .
H20A H 0.5721 0.6049 0.3751 0.035 Uiso 1 1 calc R
H20B H 0.6939 0.7572 0.4344 0.035 Uiso 1 1 calc R
C21 C 0.8276(2) 0.5950(2) 0.42214(16) 0.0294(5) Uani 1 1 d .
H21A H 0.9322 0.6423 0.4900 0.035 Uiso 1 1 calc R
H21B H 0.8073 0.4935 0.4208 0.035 Uiso 1 1 calc R
C22 C 0.8579(2) 0.6086(2) 0.31248(16) 0.0291(5) Uani 1 1 d .
H22A H 0.8745 0.7096 0.3119 0.035 Uiso 1 1 calc R
H22B H 0.7558 0.5575 0.2441 0.035 Uiso 1 1 calc R
C23 C 1.0120(2) 0.5499(2) 0.30213(17) 0.0329(5) Uani 1 1 d .
H23A H 1.1131 0.5992 0.3719 0.040 Uiso 1 1 calc R
H23B H 0.9937 0.4484 0.3010 0.040 Uiso 1 1 calc R
C24 C 1.0484(3) 0.5654(3) 0.19458(18) 0.0426(6) Uani 1 1 d .
H24A H 1.1478 0.5243 0.1930 0.064 Uiso 1 1 calc R
H24B H 1.0714 0.6658 0.1964 0.064 Uiso 1 1 calc R
H24C H 0.9496 0.5159 0.1249 0.064 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
C6 C1 C2 121.49(18) .
C6 C1 H1 119.3 .
C2 C1 H1 119.3 .
C1 C2 C3 119.96(17) .
C1 C2 C9 119.21(18) .
C3 C2 C9 120.71(17) .
C2 C3 C4 119.27(16) .
C2 C3 C7 122.50(17) .
C4 C3 C7 118.21(18) .
C4 C4 C3 120.1(2) 2_576
C4 C4 C5 119.9(2) 2_576
C3 C4 C5 119.98(16) .
C6 C5 C4 119.15(16) .
C6 C5 C8 122.53(16) .
C4 C5 C8 118.32(18) .
C1 C6 C5 120.14(17) .
C1 C6 C17 119.14(18) .
C5 C6 C17 120.67(17) .
C8 C7 C3 121.77(18) 2_576
C8 C7 H7 119.1 2_576
C3 C7 H7 119.1 .
C7 C8 C5 121.67(17) 2_576
C7 C8 H8 119.2 2_576
C5 C8 H8 119.2 .
C10 C9 C2 177.0(2) .
C9 C10 C11 177.1(2) .
C10 C11 C12 113.26(17) .
C10 C11 H11A 108.9 .
C12 C11 H11A 108.9 .
C10 C11 H11B 108.9 .
C12 C11 H11B 108.9 .
H11A C11 H11B 107.7 .
C11 C12 C13 112.81(17) .
C11 C12 H12A 109.0 .
C13 C12 H12A 109.0 .
C11 C12 H12B 109.0 .
C13 C12 H12B 109.0 .
H12A C12 H12B 107.8 .
C14 C13 C12 113.76(18) .
C14 C13 H13A 108.8 .
C12 C13 H13A 108.8 .
C14 C13 H13B 108.8 .
C12 C13 H13B 108.8 .
H13A C13 H13B 107.7 .
C13 C14 C15 114.86(18) .
C13 C14 H14A 108.6 .
C15 C14 H14A 108.6 .
C13 C14 H14B 108.6 .
C15 C14 H14B 108.6 .
H14A C14 H14B 107.5 .
C16 C15 C14 113.5(2) .
C16 C15 H15A 108.9 .
C14 C15 H15A 108.9 .
C16 C15 H15B 108.9 .
C14 C15 H15B 108.9 .
H15A C15 H15B 107.7 .
C15 C16 H16A 109.5 .
C15 C16 H16B 109.5 .
H16A C16 H16B 109.5 .
C15 C16 H16C 109.5 .
H16A C16 H16C 109.5 .
H16B C16 H16C 109.5 .
C18 C17 C6 179.0(2) .
C17 C18 C19 178.0(2) .
C18 C19 C20 113.12(17) .
C18 C19 H19A 109.0 .
C20 C19 H19A 109.0 .
C18 C19 H19B 109.0 .
C20 C19 H19B 109.0 .
H19A C19 H19B 107.8 .
C21 C20 C19 112.15(16) .
C21 C20 H20A 109.2 .
C19 C20 H20A 109.2 .
C21 C20 H20B 109.2 .
C19 C20 H20B 109.2 .
H20A C20 H20B 107.9 .
C22 C21 C20 114.63(17) .
C22 C21 H21A 108.6 .
C20 C21 H21A 108.6 .
C22 C21 H21B 108.6 .
C20 C21 H21B 108.6 .
H21A C21 H21B 107.6 .
C21 C22 C23 112.66(17) .
C21 C22 H22A 109.1 .
C23 C22 H22A 109.1 .
C21 C22 H22B 109.1 .
C23 C22 H22B 109.1 .
H22A C22 H22B 107.8 .
C24 C23 C22 113.94(18) .
C24 C23 H23A 108.8 .
C22 C23 H23A 108.8 .
C24 C23 H23B 108.8 .
C22 C23 H23B 108.8 .
H23A C23 H23B 107.7 .
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 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.393(2) .
C1 C2 1.393(2) .
C1 H1 0.9500 .
C2 C3 1.411(3) .
C2 C9 1.440(3) .
C3 C4 1.425(2) .
C3 C7 1.432(2) .
C4 C4 1.421(4) 2_576
C4 C5 1.427(2) .
C5 C6 1.410(3) .
C5 C8 1.431(2) .
C6 C17 1.437(3) .
C7 C8 1.342(3) 2_576
C7 H7 0.9500 .
C8 C7 1.342(3) 2_576
C8 H8 0.9500 .
C9 C10 1.200(3) .
C10 C11 1.466(3) .
C11 C12 1.517(3) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.520(3) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.518(3) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.523(3) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.511(3) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 C18 1.196(3) .
C18 C19 1.466(2) .
C19 C20 1.525(2) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 C21 1.522(2) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 C22 1.516(2) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 C23 1.522(2) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 C24 1.520(2) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
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 0.6(3) . .
C6 C1 C2 C9 176.62(18) . .
C1 C2 C3 C4 0.1(3) . .
C9 C2 C3 C4 -175.91(18) . .
C1 C2 C3 C7 178.63(18) . .
C9 C2 C3 C7 2.6(3) . .
C2 C3 C4 C4 178.4(2) . 2_576
C7 C3 C4 C4 -0.2(3) . 2_576
C2 C3 C4 C5 -0.9(3) . .
C7 C3 C4 C5 -179.50(18) . .
C4 C4 C5 C6 -178.2(2) 2_576 .
C3 C4 C5 C6 1.1(3) . .
C4 C4 C5 C8 1.1(3) 2_576 .
C3 C4 C5 C8 -179.67(17) . .
C2 C1 C6 C5 -0.4(3) . .
C2 C1 C6 C17 -177.87(18) . .
C4 C5 C6 C1 -0.4(3) . .
C8 C5 C6 C1 -179.65(18) . .
C4 C5 C6 C17 177.00(18) . .
C8 C5 C6 C17 -2.2(3) . .
C2 C3 C7 C8 -178.44(18) . 2_576
C4 C3 C7 C8 0.1(3) . 2_576
C6 C5 C8 C7 178.28(19) . 2_576
C4 C5 C8 C7 -1.0(3) . 2_576
C10 C11 C12 C13 -179.8(2) . .
C11 C12 C13 C14 -177.5(2) . .
C12 C13 C14 C15 179.1(2) . .
C13 C14 C15 C16 69.3(3) . .
C18 C19 C20 C21 177.10(17) . .
C19 C20 C21 C22 -175.28(17) . .
C20 C21 C22 C23 177.69(18) . .
C21 C22 C23 C24 -178.52(17) . .
