#------------------------------------------------------------------------------
#$Date: 2019-11-11 20:58:56 +0200 (Mon, 11 Nov 2019) $
#$Revision: 227347 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/59/4035954.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_4035954
loop_
_publ_author_name
'Mocanu, Anabella'
'Szűcs, Rózsa'
'Caytan, Elsa'
'Roisnel, Thierry'
'Dorcet, Vincent'
'Bouit, Pierre-Antoine'
'Nyulászi, László'
'Hissler, Muriel'
_publ_section_title
;
 Synthesis, Optical, and Redox Properties of Regioisomeric
 Benzoheterocycles-Fused Pyrene.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              957
_journal_page_last               962
_journal_paper_doi               10.1021/acs.joc.8b02884
_journal_volume                  84
_journal_year                    2019
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C57 H40 Cl2 O4 P2'
_chemical_formula_sum            'C57 H40 Cl2 O4 P2'
_chemical_formula_weight         921.73
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           'SHELXL-2017_1, CRYSCALC (Oct. 2018)'
_cell_angle_alpha                114.260(4)
_cell_angle_beta                 97.195(4)
_cell_angle_gamma                92.441(4)
_cell_formula_units_Z            1
_cell_length_a                   9.3936(8)
_cell_length_b                   11.2389(11)
_cell_length_c                   11.6385(11)
_cell_measurement_reflns_used    2751
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.86
_cell_measurement_theta_min      2.81
_cell_measurement_wavelength     0.71073
_cell_volume                     1105.37(18)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2018)'
_computing_structure_refinement  'SHELXL-2017_1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11252
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         2.986
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       prism
_exptl_crystal_F_000             478
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.590
_exptl_crystal_size_min          0.460
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.638
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         5012
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0544
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0596P)²+0.3641P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1422
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3742
_reflns_number_total             5012
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02884_si_003.cif
_cod_data_source_block           JOB
_cod_database_code               4035954
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
P1 P 0.77449(6) 0.23499(6) 0.55487(6) 0.01899(16) Uani 1 1 d . . .
O1 O 0.90841(16) 0.17616(15) 0.57991(15) 0.0258(4) Uani 1 1 d . . .
C1 C 0.6606(2) 0.1528(2) 0.4032(2) 0.0218(5) Uani 1 1 d . . .
C2 C 0.6976(3) 0.1108(2) 0.2817(2) 0.0294(6) Uani 1 1 d . . .
H2 H 0.794509 0.124572 0.270720 0.035 Uiso 1 1 calc R U .
C3 C 0.5907(3) 0.0484(3) 0.1769(2) 0.0358(6) Uani 1 1 d . . .
H3 H 0.614267 0.018590 0.093191 0.043 Uiso 1 1 calc R U .
C4 C 0.4489(3) 0.0292(3) 0.1937(2) 0.0347(6) Uani 1 1 d . . .
H4 H 0.376704 -0.013804 0.120912 0.042 Uiso 1 1 calc R U .
C5 C 0.4109(2) 0.0714(2) 0.3143(2) 0.0272(5) Uani 1 1 d . . .
H5 H 0.313398 0.058463 0.324302 0.033 Uiso 1 1 calc R U .
C6 C 0.5171(2) 0.1330(2) 0.4205(2) 0.0213(5) Uani 1 1 d . . .
C7 C 0.4995(2) 0.1810(2) 0.5568(2) 0.0204(5) Uani 1 1 d . . .
C8 C 0.3707(2) 0.1783(2) 0.6036(2) 0.0240(5) Uani 1 1 d . . .
H8 H 0.282899 0.143058 0.545971 0.029 Uiso 1 1 calc R U .
C9 C 0.3702(2) 0.2272(2) 0.7354(2) 0.0232(5) Uani 1 1 d . . .
C10 C 0.2385(2) 0.2272(3) 0.7868(2) 0.0306(6) Uani 1 1 d . . .
H10 H 0.149509 0.194748 0.730450 0.037 Uiso 1 1 calc R U .
C11 C 0.2396(3) 0.2726(3) 0.9140(2) 0.0317(6) Uani 1 1 d . . .
H11 H 0.151066 0.270914 0.944998 0.038 Uiso 1 1 calc R U .
C12 C 0.3705(3) 0.3232(2) 1.0034(2) 0.0281(5) Uani 1 1 d . . .
C13 C 0.3731(3) 0.3719(3) 1.1357(2) 0.0344(6) Uani 1 1 d . . .
H13 H 0.285808 0.370260 1.168542 0.041 Uiso 1 1 calc R U .
C14 C 0.5020(3) 0.4224(3) 1.2187(2) 0.0366(6) Uani 1 1 d . . .
H14 H 0.502049 0.455105 1.308091 0.044 Uiso 1 1 calc R U .
C15 C 0.6308(3) 0.4258(3) 1.1732(2) 0.0328(6) Uani 1 1 d . . .
H15 H 0.717806 0.461913 1.231797 0.039 Uiso 1 1 calc R U .
C16 C 0.6346(2) 0.3770(2) 1.0425(2) 0.0261(5) Uani 1 1 d . . .
C17 C 0.5021(2) 0.3255(2) 0.9556(2) 0.0235(5) Uani 1 1 d . . .
C18 C 0.5027(2) 0.2771(2) 0.8217(2) 0.0219(5) Uani 1 1 d . . .
C19 C 0.6351(2) 0.2807(2) 0.7742(2) 0.0213(5) Uani 1 1 d . . .
C20 C 0.7663(2) 0.3322(2) 0.8640(2) 0.0254(5) Uani 1 1 d . . .
H20 H 0.855273 0.334045 0.833556 0.030 Uiso 1 1 calc R U .
C21 C 0.7653(2) 0.3780(2) 0.9908(2) 0.0281(5) Uani 1 1 d . . .
H21 H 0.853919 0.411833 1.047605 0.034 Uiso 1 1 calc R U .
C22 C 0.6300(2) 0.2332(2) 0.6418(2) 0.0196(5) Uani 1 1 d . . .
C23 C 0.8167(2) 0.4023(2) 0.5796(2) 0.0190(5) Uani 1 1 d . . .
C24 C 0.9486(2) 0.4699(2) 0.6507(2) 0.0263(5) Uani 1 1 d . . .
H24 H 1.016721 0.426971 0.683314 0.032 Uiso 1 1 calc R U .
C25 C 0.9798(3) 0.5998(3) 0.6737(2) 0.0320(6) Uani 1 1 d . . .
H25 H 1.069488 0.646123 0.722341 0.038 Uiso 1 1 calc R U .
C26 C 0.8812(3) 0.6624(3) 0.6262(3) 0.0349(6) Uani 1 1 d . . .
H26 H 0.902904 0.751906 0.643058 0.042 Uiso 1 1 calc R U .
C27 C 0.7510(3) 0.5954(2) 0.5541(3) 0.0318(6) Uani 1 1 d . . .
H27 H 0.683803 0.638575 0.520851 0.038 Uiso 1 1 calc R U .
C28 C 0.7188(2) 0.4654(2) 0.5305(2) 0.0252(5) Uani 1 1 d . . .
H28 H 0.629627 0.419143 0.480577 0.030 Uiso 1 1 calc R U .
C51 C 1.0514(9) 0.0403(8) 0.0785(7) 0.076(2) Uani 0.5 1 d . . P
H51A H 1.027019 0.035567 0.156937 0.091 Uiso 0.5 1 calc R U P
H51B H 1.143521 0.097092 0.102657 0.091 Uiso 0.5 1 calc R U P
Cl1 Cl 0.92063(9) 0.11478(8) 0.02560(9) 0.0562(2) Uani 1 1 d . . .
O2 O 0.94391(19) -0.04457(19) 0.6294(2) 0.0357(5) Uani 1 1 d . . .
HW1 H 0.997(3) -0.086(3) 0.558(3) 0.050 Uiso 1 1 d . . .
HW2 H 0.927(3) 0.028(3) 0.630(3) 0.050 Uiso 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
O1 P1 C1 118.51(10) . .
O1 P1 C22 118.17(10) . .
C1 P1 C22 92.91(10) . .
O1 P1 C23 110.80(10) . .
C1 P1 C23 107.48(10) . .
C22 P1 C23 107.22(10) . .
C2 C1 C6 121.0(2) . .
C2 C1 P1 128.75(17) . .
C6 C1 P1 110.21(17) . .
C3 C2 C1 118.8(2) . .
C3 C2 H2 120.6 . .
C1 C2 H2 120.6 . .
C2 C3 C4 120.3(2) . .
C2 C3 H3 119.9 . .
C4 C3 H3 119.9 . .
C5 C4 C3 121.3(2) . .
C5 C4 H4 119.3 . .
C3 C4 H4 119.3 . .
C4 C5 C6 119.2(2) . .
C4 C5 H5 120.4 . .
C6 C5 H5 120.4 . .
C5 C6 C1 119.4(2) . .
C5 C6 C7 127.4(2) . .
C1 C6 C7 113.20(19) . .
C8 C7 C22 120.1(2) . .
C8 C7 C6 126.39(19) . .
C22 C7 C6 113.51(18) . .
C7 C8 C9 120.24(19) . .
C7 C8 H8 119.9 . .
C9 C8 H8 119.9 . .
C8 C9 C18 119.82(19) . .
C8 C9 C10 121.6(2) . .
C18 C9 C10 118.6(2) . .
C11 C10 C9 121.0(2) . .
C11 C10 H10 119.5 . .
C9 C10 H10 119.5 . .
C10 C11 C12 121.9(2) . .
C10 C11 H11 119.1 . .
C12 C11 H11 119.1 . .
C13 C12 C17 119.1(2) . .
C13 C12 C11 122.5(2) . .
C17 C12 C11 118.4(2) . .
C14 C13 C12 120.5(2) . .
C14 C13 H13 119.7 . .
C12 C13 H13 119.7 . .
C13 C14 C15 120.9(2) . .
C13 C14 H14 119.6 . .
C15 C14 H14 119.6 . .
C14 C15 C16 121.0(2) . .
C14 C15 H15 119.5 . .
C16 C15 H15 119.5 . .
C15 C16 C17 118.8(2) . .
C15 C16 C21 123.0(2) . .
C17 C16 C21 118.2(2) . .
C12 C17 C18 120.3(2) . .
C12 C17 C16 119.8(2) . .
C18 C17 C16 119.9(2) . .
C17 C18 C9 119.8(2) . .
C17 C18 C19 120.1(2) . .
C9 C18 C19 120.1(2) . .
C22 C19 C18 118.00(19) . .
C22 C19 C20 123.4(2) . .
C18 C19 C20 118.6(2) . .
C21 C20 C19 121.1(2) . .
C21 C20 H20 119.4 . .
C19 C20 H20 119.4 . .
C20 C21 C16 122.0(2) . .
C20 C21 H21 119.0 . .
C16 C21 H21 119.0 . .
C19 C22 C7 121.66(19) . .
C19 C22 P1 128.31(16) . .
C7 C22 P1 109.95(16) . .
C28 C23 C24 119.7(2) . .
C28 C23 P1 120.93(16) . .
C24 C23 P1 119.41(17) . .
C25 C24 C23 119.7(2) . .
C25 C24 H24 120.1 . .
C23 C24 H24 120.1 . .
C26 C25 C24 120.3(2) . .
C26 C25 H25 119.9 . .
C24 C25 H25 119.9 . .
C25 C26 C27 120.3(2) . .
C25 C26 H26 119.8 . .
C27 C26 H26 119.8 . .
C26 C27 C28 119.8(2) . .
C26 C27 H27 120.1 . .
C28 C27 H27 120.1 . .
C27 C28 C23 120.2(2) . .
C27 C28 H28 119.9 . .
C23 C28 H28 119.9 . .
Cl1 C51 Cl1 116.9(4) . 2_755
Cl1 C51 H51A 108.1 . .
Cl1 C51 H51A 108.1 2_755 .
Cl1 C51 H51B 108.1 . .
Cl1 C51 H51B 108.1 2_755 .
H51A C51 H51B 107.3 . .
C51 Cl1 C51 63.1(4) . 2_755
HW1 O2 HW2 105(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 O1 1.4973(16) .
P1 C1 1.793(2) .
P1 C22 1.795(2) .
P1 C23 1.799(2) .
C1 C2 1.390(3) .
C1 C6 1.409(3) .
C2 C3 1.385(3) .
C2 H2 0.9500 .
C3 C4 1.390(4) .
C3 H3 0.9500 .
C4 C5 1.384(3) .
C4 H4 0.9500 .
C5 C6 1.390(3) .
C5 H5 0.9500 .
C6 C7 1.484(3) .
C7 C8 1.391(3) .
C7 C22 1.408(3) .
C8 C9 1.402(3) .
C8 H8 0.9500 .
C9 C18 1.427(3) .
C9 C10 1.440(3) .
C10 C11 1.352(3) .
C10 H10 0.9500 .
C11 C12 1.432(3) .
C11 H11 0.9500 .
C12 C13 1.403(3) .
C12 C17 1.421(3) .
C13 C14 1.386(4) .
C13 H13 0.9500 .
C14 C15 1.386(4) .
C14 H14 0.9500 .
C15 C16 1.395(3) .
C15 H15 0.9500 .
C16 C17 1.432(3) .
C16 C21 1.435(3) .
C17 C18 1.425(3) .
C18 C19 1.428(3) .
C19 C22 1.402(3) .
C19 C20 1.437(3) .
C20 C21 1.351(3) .
C20 H20 0.9500 .
C21 H21 0.9500 .
C23 C28 1.390(3) .
C23 C24 1.394(3) .
C24 C25 1.382(3) .
C24 H24 0.9500 .
C25 C26 1.381(4) .
C25 H25 0.9500 .
C26 C27 1.383(4) .
C26 H26 0.9500 .
C27 C28 1.383(3) .
C27 H27 0.9500 .
C28 H28 0.9500 .
C51 Cl1 1.706(7) .
C51 Cl1 1.720(7) 2_755
C51 H51A 0.9900 .
C51 H51B 0.9900 .
O2 HW1 0.98(3) .
O2 HW2 0.84(3) .
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
O1 P1 C1 C2 -52.1(3) . .
C22 P1 C1 C2 -176.5(2) . .
C23 P1 C1 C2 74.4(2) . .
O1 P1 C1 C6 127.91(16) . .
C22 P1 C1 C6 3.47(17) . .
C23 P1 C1 C6 -105.60(17) . .
C6 C1 C2 C3 -0.1(4) . .
P1 C1 C2 C3 179.8(2) . .
C1 C2 C3 C4 0.4(4) . .
C2 C3 C4 C5 0.0(4) . .
C3 C4 C5 C6 -0.7(4) . .
C4 C5 C6 C1 0.9(4) . .
C4 C5 C6 C7 -177.8(2) . .
C2 C1 C6 C5 -0.5(3) . .
P1 C1 C6 C5 179.50(18) . .
C2 C1 C6 C7 178.4(2) . .
P1 C1 C6 C7 -1.6(2) . .
C5 C6 C7 C8 -3.0(4) . .
C1 C6 C7 C8 178.2(2) . .
C5 C6 C7 C22 176.9(2) . .
C1 C6 C7 C22 -1.9(3) . .
C22 C7 C8 C9 0.0(3) . .
C6 C7 C8 C9 180.0(2) . .
C7 C8 C9 C18 -1.6(3) . .
C7 C8 C9 C10 179.3(2) . .
C8 C9 C10 C11 178.8(2) . .
C18 C9 C10 C11 -0.3(4) . .
C9 C10 C11 C12 0.3(4) . .
C10 C11 C12 C13 179.3(3) . .
C10 C11 C12 C17 0.2(4) . .
C17 C12 C13 C14 0.5(4) . .
C11 C12 C13 C14 -178.7(2) . .
C12 C13 C14 C15 -0.1(4) . .
C13 C14 C15 C16 -0.8(4) . .
C14 C15 C16 C17 1.3(4) . .
C14 C15 C16 C21 -179.8(2) . .
C13 C12 C17 C18 -179.8(2) . .
C11 C12 C17 C18 -0.6(3) . .
C13 C12 C17 C16 0.0(4) . .
C11 C12 C17 C16 179.2(2) . .
C15 C16 C17 C12 -0.9(3) . .
C21 C16 C17 C12 -179.9(2) . .
C15 C16 C17 C18 178.9(2) . .
C21 C16 C17 C18 -0.1(3) . .
C12 C17 C18 C9 0.6(3) . .
C16 C17 C18 C9 -179.2(2) . .
C12 C17 C18 C19 179.4(2) . .
C16 C17 C18 C19 -0.4(3) . .
C8 C9 C18 C17 -179.3(2) . .
C10 C9 C18 C17 -0.1(3) . .
C8 C9 C18 C19 1.9(3) . .
C10 C9 C18 C19 -178.9(2) . .
C17 C18 C19 C22 -179.4(2) . .
C9 C18 C19 C22 -0.6(3) . .
C17 C18 C19 C20 0.9(3) . .
C9 C18 C19 C20 179.7(2) . .
C22 C19 C20 C21 179.4(2) . .
C18 C19 C20 C21 -0.9(3) . .
C19 C20 C21 C16 0.4(4) . .
C15 C16 C21 C20 -178.9(2) . .
C17 C16 C21 C20 0.1(4) . .
C18 C19 C22 C7 -1.1(3) . .
C20 C19 C22 C7 178.7(2) . .
C18 C19 C22 P1 175.37(17) . .
C20 C19 C22 P1 -4.9(3) . .
C8 C7 C22 C19 1.4(3) . .
C6 C7 C22 C19 -178.6(2) . .
C8 C7 C22 P1 -175.65(17) . .
C6 C7 C22 P1 4.4(2) . .
O1 P1 C22 C19 54.0(2) . .
C1 P1 C22 C19 178.7(2) . .
C23 P1 C22 C19 -72.0(2) . .
O1 P1 C22 C7 -129.20(16) . .
C1 P1 C22 C7 -4.49(17) . .
C23 P1 C22 C7 104.81(17) . .
O1 P1 C23 C28 162.60(18) . .
C1 P1 C23 C28 31.7(2) . .
C22 P1 C23 C28 -67.1(2) . .
O1 P1 C23 C24 -18.4(2) . .
C1 P1 C23 C24 -149.31(18) . .
C22 P1 C23 C24 111.87(19) . .
C28 C23 C24 C25 1.1(3) . .
P1 C23 C24 C25 -177.89(19) . .
C23 C24 C25 C26 -0.2(4) . .
C24 C25 C26 C27 -0.7(4) . .
C25 C26 C27 C28 0.6(4) . .
C26 C27 C28 C23 0.3(4) . .
C24 C23 C28 C27 -1.2(3) . .
P1 C23 C28 C27 177.79(18) . .
Cl1 C51 Cl1 C51 0.001(0) 2_755 2_755
