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#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/24/1542451.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_1542451
loop_
_publ_author_name
'Sabounchei, Seyyed Javad'
'Nemattalab, Hassan'
'Khavasi, Hamid Reza'
_publ_section_title
;
 Crystal Structure of 4'-Chlorobenzoylmethylenetriphenylphosphorane ylide,
 C₂₆H₂₀ClOP
;
_journal_name_full               'X-ray Structure Analysis Online'
_journal_page_first              35
_journal_page_last               36
_journal_paper_doi               10.2116/xraystruct.26.35
_journal_volume                  26
_journal_year                    2010
_chemical_formula_sum            'C26 H20 Cl O P'
_chemical_formula_weight         414.84
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 100.366(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.6184(9)
_cell_length_b                   10.9196(6)
_cell_length_c                   23.5465(12)
_cell_measurement_reflns_used    2643
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.19
_cell_measurement_theta_min      2.24
_cell_volume                     4203.2(4)
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_molecular_graphics    'X-Step32 1.07e (Stoe & Cie GmbH, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 6.6667
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_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  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15184
_diffrn_reflns_theta_full        29.19
_diffrn_reflns_theta_max         29.19
_diffrn_reflns_theta_min         2.24
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.020
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'shape of crystal determined optically'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         5571
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0401P)²+4.3656P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1005
_reflns_number_gt                5276
_reflns_number_total             5571
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            26_35_1.cif
_cod_data_source_block           kh245-abs1
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C26 H20 Cl1 O1 P1'
_cod_database_code               1542451
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.23697(7) 0.93523(12) 0.58313(5) 0.0223(2) Uani 1 1 d . . .
H1 H 0.1988 0.8724 0.5753 0.027 Uiso 1 1 calc R . .
C2 C 0.28426(8) 0.94480(12) 0.63795(6) 0.0234(2) Uani 1 1 d . . .
H2 H 0.2778 0.8895 0.6668 0.028 Uiso 1 1 calc R . .
C3 C 0.34139(7) 1.03867(12) 0.64869(5) 0.0225(2) Uani 1 1 d . . .
C4 C 0.35058(8) 1.12406(12) 0.60685(6) 0.0244(2) Uani 1 1 d . . .
H4 H 0.3881 1.1877 0.6151 0.029 Uiso 1 1 calc R . .
C5 C 0.30267(8) 1.11287(12) 0.55223(6) 0.0227(2) Uani 1 1 d . . .
H5 H 0.3087 1.1693 0.5237 0.027 Uiso 1 1 calc R . .
C6 C 0.24568(7) 1.01841(11) 0.53949(5) 0.0200(2) Uani 1 1 d . . .
C7 C 0.19415(7) 1.01437(11) 0.47971(5) 0.0209(2) Uani 1 1 d . . .
C8 C 0.13832(8) 0.91799(11) 0.46551(5) 0.0221(2) Uani 1 1 d . . .
H8 H 0.1371 0.8542 0.4915 0.026 Uiso 1 1 calc R . .
C9 C 0.00273(7) 0.79195(11) 0.40555(5) 0.0181(2) Uani 1 1 d . . .
C10 C 0.03525(8) 0.67389(11) 0.41626(6) 0.0242(2) Uani 1 1 d . . .
H10 H 0.0909 0.6605 0.4180 0.029 Uiso 1 1 calc R . .
C11 C -0.01555(9) 0.57710(12) 0.42429(7) 0.0295(3) Uani 1 1 d . . .
H11 H 0.0060 0.4988 0.4312 0.035 Uiso 1 1 calc R . .
C12 C -0.09885(9) 0.59706(12) 0.42197(6) 0.0281(3) Uani 1 1 d . . .
H12 H -0.1328 0.5320 0.4274 0.034 Uiso 1 1 calc R . .
C13 C -0.13131(8) 0.71353(12) 0.41154(6) 0.0252(3) Uani 1 1 d . . .
H13 H -0.1869 0.7265 0.4102 0.030 Uiso 1 1 calc R . .
C14 C -0.08091(7) 0.81121(11) 0.40313(5) 0.0209(2) Uani 1 1 d . . .
H14 H -0.1029 0.8892 0.3959 0.025 Uiso 1 1 calc R . .
C15 C 0.11791(7) 0.89223(12) 0.33680(5) 0.0213(2) Uani 1 1 d . . .
C16 C 0.09346(8) 0.79696(12) 0.29822(5) 0.0249(2) Uani 1 1 d . . .
H16 H 0.0519 0.7442 0.3043 0.030 Uiso 1 1 calc R . .
C17 C 0.13133(9) 0.78054(14) 0.25039(6) 0.0288(3) Uani 1 1 d . . .
H17 H 0.1146 0.7172 0.2245 0.035 Uiso 1 1 calc R . .
C18 C 0.19351(9) 0.85811(15) 0.24141(6) 0.0326(3) Uani 1 1 d . . .
H18 H 0.2191 0.8463 0.2098 0.039 Uiso 1 1 calc R . .
C19 C 0.21774(10) 0.95349(17) 0.27940(7) 0.0391(4) Uani 1 1 d . . .
H19 H 0.2595 1.0057 0.2731 0.047 Uiso 1 1 calc R . .
C20 C 0.18012(9) 0.97173(15) 0.32693(6) 0.0335(3) Uani 1 1 d . . .
H20 H 0.1962 1.0365 0.3521 0.040 Uiso 1 1 calc R . .
C21 C 0.01185(7) 1.05504(11) 0.38538(5) 0.0204(2) Uani 1 1 d . . .
C22 C 0.00388(8) 1.13485(12) 0.43032(6) 0.0234(2) Uani 1 1 d . . .
H22 H 0.0304 1.1181 0.4678 0.028 Uiso 1 1 calc R . .
C23 C -0.04396(9) 1.23972(12) 0.41876(6) 0.0285(3) Uani 1 1 d . . .
H23 H -0.0492 1.2933 0.4486 0.034 Uiso 1 1 calc R . .
C24 C -0.08381(9) 1.26472(13) 0.36300(7) 0.0325(3) Uani 1 1 d . . .
H24 H -0.1153 1.3353 0.3556 0.039 Uiso 1 1 calc R . .
C25 C -0.07691(10) 1.18484(14) 0.31830(7) 0.0340(3) Uani 1 1 d . . .
H25 H -0.1043 1.2013 0.2810 0.041 Uiso 1 1 calc R . .
C26 C -0.02896(9) 1.08023(12) 0.32934(6) 0.0276(3) Uani 1 1 d . . .
H26 H -0.0240 1.0269 0.2994 0.033 Uiso 1 1 calc R . .
O1 O 0.20208(6) 1.09992(9) 0.44536(4) 0.0267(2) Uani 1 1 d . . .
P1 P 0.072052(18) 0.91687(3) 0.400371(12) 0.01786(8) Uani 1 1 d . . .
Cl1 Cl 0.40391(2) 1.04959(3) 0.716440(14) 0.03119(9) 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'
N N 0.0061 0.0033 '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'
Cd Cd -0.8075 1.2024 '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
C2 C1 C6 121.20(11) . .
C2 C1 H1 119.4 . .
C6 C1 H1 119.4 . .
C1 C2 C3 118.59(12) . .
C1 C2 H2 120.7 . .
C3 C2 H2 120.7 . .
C4 C3 C2 121.77(12) . .
C4 C3 Cl1 118.75(10) . .
C2 C3 Cl1 119.48(10) . .
C3 C4 C5 118.73(11) . .
C3 C4 H4 120.6 . .
C5 C4 H4 120.6 . .
C4 C5 C6 121.14(12) . .
C4 C5 H5 119.4 . .
C6 C5 H5 119.4 . .
C5 C6 C1 118.55(11) . .
C5 C6 C7 118.08(11) . .
C1 C6 C7 123.33(11) . .
O1 C7 C8 123.04(11) . .
O1 C7 C6 118.03(11) . .
C8 C7 C6 118.91(11) . .
C7 C8 P1 120.51(9) . .
C7 C8 H8 119.7 . .
P1 C8 H8 119.7 . .
C14 C9 C10 119.60(11) . .
C14 C9 P1 121.76(9) . .
C10 C9 P1 118.50(9) . .
C11 C10 C9 120.04(12) . .
C11 C10 H10 120.0 . .
C9 C10 H10 120.0 . .
C10 C11 C12 120.04(12) . .
C10 C11 H11 120.0 . .
C12 C11 H11 120.0 . .
C13 C12 C11 120.20(12) . .
C13 C12 H12 119.9 . .
C11 C12 H12 119.9 . .
C12 C13 C14 120.22(12) . .
C12 C13 H13 119.9 . .
C14 C13 H13 119.9 . .
C13 C14 C9 119.91(11) . .
C13 C14 H14 120.0 . .
C9 C14 H14 120.0 . .
C16 C15 C20 119.47(12) . .
C16 C15 P1 122.10(9) . .
C20 C15 P1 118.43(10) . .
C15 C16 C17 120.05(12) . .
C15 C16 H16 120.0 . .
C17 C16 H16 120.0 . .
C18 C17 C16 120.17(13) . .
C18 C17 H17 119.9 . .
C16 C17 H17 119.9 . .
C17 C18 C19 120.05(13) . .
C17 C18 H18 120.0 . .
C19 C18 H18 120.0 . .
C18 C19 C20 120.46(14) . .
C18 C19 H19 119.8 . .
C20 C19 H19 119.8 . .
C19 C20 C15 119.77(14) . .
C19 C20 H20 120.1 . .
C15 C20 H20 120.1 . .
C22 C21 C26 119.79(12) . .
C22 C21 P1 119.83(10) . .
C26 C21 P1 120.35(10) . .
C23 C22 C21 119.61(12) . .
C23 C22 H22 120.2 . .
C21 C22 H22 120.2 . .
C24 C23 C22 120.35(13) . .
C24 C23 H23 119.8 . .
C22 C23 H23 119.8 . .
C23 C24 C25 120.25(13) . .
C23 C24 H24 119.9 . .
C25 C24 H24 119.9 . .
C24 C25 C26 119.84(14) . .
C24 C25 H25 120.1 . .
C26 C25 H25 120.1 . .
C25 C26 C21 120.16(13) . .
C25 C26 H26 119.9 . .
C21 C26 H26 119.9 . .
C8 P1 C9 105.03(6) . .
C8 P1 C21 114.26(6) . .
C9 P1 C21 107.84(5) . .
C8 P1 C15 116.07(6) . .
C9 P1 C15 108.13(6) . .
C21 P1 C15 105.18(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3890(17) .
C1 C6 1.3983(17) .
C1 H1 0.9300 .
C2 C3 1.3892(17) .
C2 H2 0.9300 .
C3 C4 1.3847(19) .
C3 Cl1 1.7441(13) .
C4 C5 1.3907(18) .
C4 H4 0.9300 .
C5 C6 1.3960(16) .
C5 H5 0.9300 .
C6 C7 1.5110(16) .
C7 O1 1.2580(15) .
C7 C8 1.4031(16) .
C8 P1 1.7198(13) .
C8 H8 0.9300 .
C9 C14 1.3968(16) .
C9 C10 1.4031(17) .
C9 P1 1.8037(12) .
C10 C11 1.3867(18) .
C10 H10 0.9300 .
C11 C12 1.3927(19) .
C11 H11 0.9300 .
C12 C13 1.3860(19) .
C12 H12 0.9300 .
C13 C14 1.3923(17) .
C13 H13 0.9300 .
C14 H14 0.9300 .
C15 C16 1.3927(18) .
C15 C20 1.4011(18) .
C15 P1 1.8177(12) .
C16 C17 1.3970(18) .
C16 H16 0.9300 .
C17 C18 1.382(2) .
C17 H17 0.9300 .
C18 C19 1.385(2) .
C18 H18 0.9300 .
C19 C20 1.391(2) .
C19 H19 0.9300 .
C20 H20 0.9300 .
C21 C22 1.3954(17) .
C21 C26 1.3982(17) .
C21 P1 1.8097(13) .
C22 C23 1.3926(19) .
C22 H22 0.9300 .
C23 C24 1.387(2) .
C23 H23 0.9300 .
C24 C25 1.388(2) .
C24 H24 0.9300 .
C25 C26 1.3903(19) .
C25 H25 0.9300 .
C26 H26 0.9300 .
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 -0.54(19) . . . .
C1 C2 C3 C4 1.80(19) . . . .
C1 C2 C3 Cl1 -177.85(10) . . . .
C2 C3 C4 C5 -1.82(19) . . . .
Cl1 C3 C4 C5 177.83(10) . . . .
C3 C4 C5 C6 0.59(19) . . . .
C4 C5 C6 C1 0.61(18) . . . .
C4 C5 C6 C7 178.26(11) . . . .
C2 C1 C6 C5 -0.63(19) . . . .
C2 C1 C6 C7 -178.16(11) . . . .
C5 C6 C7 O1 -3.69(17) . . . .
C1 C6 C7 O1 173.84(12) . . . .
C5 C6 C7 C8 178.05(11) . . . .
C1 C6 C7 C8 -4.42(18) . . . .
O1 C7 C8 P1 -3.98(18) . . . .
C6 C7 C8 P1 174.18(9) . . . .
C14 C9 C10 C11 0.09(19) . . . .
P1 C9 C10 C11 175.75(11) . . . .
C9 C10 C11 C12 -0.3(2) . . . .
C10 C11 C12 C13 0.1(2) . . . .
C11 C12 C13 C14 0.2(2) . . . .
C12 C13 C14 C9 -0.4(2) . . . .
C10 C9 C14 C13 0.24(18) . . . .
P1 C9 C14 C13 -175.28(10) . . . .
C20 C15 C16 C17 0.5(2) . . . .
P1 C15 C16 C17 -179.06(10) . . . .
C15 C16 C17 C18 0.5(2) . . . .
C16 C17 C18 C19 -0.9(2) . . . .
C17 C18 C19 C20 0.3(3) . . . .
C18 C19 C20 C15 0.7(3) . . . .
C16 C15 C20 C19 -1.1(2) . . . .
P1 C15 C20 C19 178.49(13) . . . .
C26 C21 C22 C23 -0.75(18) . . . .
P1 C21 C22 C23 -178.62(9) . . . .
C21 C22 C23 C24 0.27(19) . . . .
C22 C23 C24 C25 0.5(2) . . . .
C23 C24 C25 C26 -0.9(2) . . . .
C24 C25 C26 C21 0.4(2) . . . .
C22 C21 C26 C25 0.4(2) . . . .
P1 C21 C26 C25 178.29(11) . . . .
C7 C8 P1 C9 -171.32(10) . . . .
C7 C8 P1 C21 -53.36(12) . . . .
C7 C8 P1 C15 69.34(12) . . . .
C14 C9 P1 C8 116.91(10) . . . .
C10 C9 P1 C8 -58.65(11) . . . .
C14 C9 P1 C21 -5.31(11) . . . .
C10 C9 P1 C21 179.12(10) . . . .
C14 C9 P1 C15 -118.57(10) . . . .
C10 C9 P1 C15 65.86(11) . . . .
C22 C21 P1 C8 -18.01(12) . . . .
C26 C21 P1 C8 164.13(10) . . . .
C22 C21 P1 C9 98.34(10) . . . .
C26 C21 P1 C9 -79.52(11) . . . .
C22 C21 P1 C15 -146.44(10) . . . .
C26 C21 P1 C15 35.70(12) . . . .
C16 C15 P1 C8 123.35(11) . . . .
C20 C15 P1 C8 -56.25(13) . . . .
C16 C15 P1 C9 5.71(12) . . . .
C20 C15 P1 C9 -173.90(11) . . . .
C16 C15 P1 C21 -109.30(11) . . . .
C20 C15 P1 C21 71.09(12) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139048041
