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#$Date: 2024-10-04 07:50:01 +0300 (Fri, 04 Oct 2024) $
#$Revision: 295037 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/38/7133829.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_7133829
loop_
_publ_author_name
'Gurram, Durga Prasad'
'Marri, Gangababu'
'Jothimani, Naveen'
'Chen, Yi-Ru'
'Lin, Wenwei'
_publ_section_title
;
 Diversity-oriented synthesis of chromone inden-1-one-fused
 cyclopentadienylides and C-acylated chromone adducts via
 allylic phosphorus ylides.
;
_journal_issue                   72
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9817
_journal_page_last               9820
_journal_paper_doi               10.1039/d4cc03210a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C31 H35 O3 P'
_chemical_formula_sum            'C31 H35 O3 P'
_chemical_formula_weight         486.56
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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
_audit_update_record
;
2024-06-03 deposited with the CCDC.	2024-08-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.690(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4838(16)
_cell_length_b                   21.180(2)
_cell_length_c                   10.3247(11)
_cell_measurement_reflns_used    4657
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.802
_cell_measurement_theta_min      2.206
_cell_volume                     2711.3(5)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'phi scan & omega scan'
_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  0.0956
_diffrn_reflns_av_sigmaI/netI    0.0753
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            25869
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.9974
_exptl_absorpt_correction_T_min  0.9693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4800
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0534
_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)+(0.0601P)²+0.9691P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1428
_reflns_number_gt                3374
_reflns_number_total             4800
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4cc03210a3.cif
_cod_data_source_block           d24152
_cod_original_cell_volume        2711.4(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7133829
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3700(2) 0.50747(11) 0.6429(2) 0.0330(6) Uani 1 1 d . . .
H1A H 0.4165 0.4976 0.5742 0.040 Uiso 1 1 calc R . .
H1AB H 0.4052 0.5420 0.6968 0.040 Uiso 1 1 calc R . .
C2 C 0.3645(2) 0.44879(12) 0.7297(3) 0.0398(7) Uani 1 1 d . . .
H2A H 0.3124 0.4564 0.7932 0.048 Uiso 1 1 calc R . .
H2AB H 0.3385 0.4123 0.6748 0.048 Uiso 1 1 calc R . .
C3 C 0.4740(3) 0.43319(14) 0.8026(3) 0.0508(8) Uani 1 1 d . . .
H3A H 0.4999 0.4699 0.8567 0.061 Uiso 1 1 calc R . .
H3AB H 0.5259 0.4258 0.7386 0.061 Uiso 1 1 calc R . .
C4 C 0.4723(3) 0.37556(17) 0.8897(3) 0.0732(11) Uani 1 1 d . . .
H4A H 0.4522 0.3383 0.8361 0.110 Uiso 1 1 calc R . .
H4B H 0.4197 0.3820 0.9519 0.110 Uiso 1 1 calc R . .
H4C H 0.5441 0.3692 0.9375 0.110 Uiso 1 1 calc R . .
C5 C 0.1544(2) 0.54573(11) 0.6905(2) 0.0325(6) Uani 1 1 d . . .
H5A H 0.0870 0.5662 0.6514 0.039 Uiso 1 1 calc R . .
H5AB H 0.1353 0.5036 0.7227 0.039 Uiso 1 1 calc R . .
C6 C 0.2035(2) 0.58527(12) 0.8060(2) 0.0373(7) Uani 1 1 d . . .
H6A H 0.2686 0.5635 0.8483 0.045 Uiso 1 1 calc R . .
H6AB H 0.2265 0.6265 0.7733 0.045 Uiso 1 1 calc R . .
C7 C 0.1269(3) 0.59678(14) 0.9065(3) 0.0502(8) Uani 1 1 d . . .
H7A H 0.0979 0.5558 0.9326 0.060 Uiso 1 1 calc R . .
H7AB H 0.0655 0.6225 0.8668 0.060 Uiso 1 1 calc R . .
C8 C 0.1802(3) 0.63021(18) 1.0267(3) 0.0780(12) Uani 1 1 d . . .
H8A H 0.2080 0.6712 1.0018 0.117 Uiso 1 1 calc R . .
H8B H 0.2399 0.6044 1.0678 0.117 Uiso 1 1 calc R . .
H8C H 0.1272 0.6367 1.0884 0.117 Uiso 1 1 calc R . .
C9 C 0.1861(2) 0.47753(12) 0.4507(3) 0.0396(7) Uani 1 1 d . . .
H9A H 0.1987 0.4351 0.4898 0.048 Uiso 1 1 calc R . .
H9AB H 0.1072 0.4841 0.4349 0.048 Uiso 1 1 calc R . .
C10 C 0.2317(2) 0.47899(12) 0.3209(2) 0.0387(7) Uani 1 1 d . . .
H10A H 0.2180 0.5211 0.2809 0.046 Uiso 1 1 calc R . .
H10B H 0.3109 0.4731 0.3367 0.046 Uiso 1 1 calc R . .
C11 C 0.1852(3) 0.42978(17) 0.2270(3) 0.0712(11) Uani 1 1 d . . .
H11A H 0.1056 0.4336 0.2171 0.085 Uiso 1 1 calc R . .
H11B H 0.2040 0.3876 0.2644 0.085 Uiso 1 1 calc R . .
C12 C 0.2233(4) 0.43383(18) 0.0940(3) 0.0869(14) Uani 1 1 d . . .
H12A H 0.1861 0.4018 0.0368 0.130 Uiso 1 1 calc R . .
H12B H 0.3013 0.4264 0.1017 0.130 Uiso 1 1 calc R . .
H12C H 0.2072 0.4759 0.0572 0.130 Uiso 1 1 calc R . .
C13 C 0.2627(2) 0.60806(11) 0.4876(2) 0.0267(6) Uani 1 1 d . . .
C14 C 0.1791(2) 0.64343(11) 0.4128(2) 0.0269(6) Uani 1 1 d . . .
C15 C 0.0661(2) 0.63351(12) 0.3850(2) 0.0323(6) Uani 1 1 d . . .
C16 C 0.0111(2) 0.68124(12) 0.2952(2) 0.0307(6) Uani 1 1 d . . .
C17 C -0.0992(2) 0.67665(13) 0.2533(3) 0.0395(7) Uani 1 1 d . . .
H17 H -0.1400 0.6434 0.2854 0.047 Uiso 1 1 calc R . .
C18 C -0.1497(2) 0.71932(14) 0.1669(3) 0.0470(8) Uani 1 1 d . . .
H18 H -0.2247 0.7155 0.1393 0.056 Uiso 1 1 calc R . .
C19 C -0.0906(2) 0.76829(14) 0.1195(3) 0.0469(8) Uani 1 1 d . . .
H19 H -0.1255 0.7975 0.0587 0.056 Uiso 1 1 calc R . .
C20 C 0.0169(2) 0.77473(12) 0.1597(3) 0.0392(7) Uani 1 1 d . . .
H20 H 0.0566 0.8087 0.1285 0.047 Uiso 1 1 calc R . .
C21 C 0.0677(2) 0.73105(11) 0.2468(2) 0.0312(6) Uani 1 1 d . . .
C22 C 0.2295(2) 0.69586(10) 0.3580(2) 0.0281(6) Uani 1 1 d . . .
C23 C 0.3386(2) 0.69420(11) 0.3935(2) 0.0287(6) Uani 1 1 d . . .
C24 C 0.4395(2) 0.72728(11) 0.3748(2) 0.0298(6) Uani 1 1 d . . .
C25 C 0.4628(2) 0.77998(12) 0.3051(3) 0.0360(6) Uani 1 1 d . . .
H25 H 0.4069 0.8036 0.2569 0.043 Uiso 1 1 calc R . .
C26 C 0.5709(2) 0.79790(12) 0.3071(3) 0.0393(7) Uani 1 1 d . . .
H26 H 0.5885 0.8341 0.2595 0.047 Uiso 1 1 calc R . .
C27 C 0.6527(2) 0.76391(12) 0.3772(2) 0.0380(7) Uani 1 1 d . . .
H27 H 0.7255 0.7771 0.3781 0.046 Uiso 1 1 calc R . .
C28 C 0.6285(2) 0.71070(12) 0.4463(2) 0.0336(6) Uani 1 1 d . . .
H28 H 0.6842 0.6868 0.4941 0.040 Uiso 1 1 calc R . .
C29 C 0.5226(2) 0.69316(11) 0.4444(2) 0.0294(6) Uani 1 1 d . . .
C30 C 0.4784(2) 0.63606(11) 0.5072(2) 0.0299(6) Uani 1 1 d . . .
C31 C 0.3603(2) 0.64021(11) 0.4728(2) 0.0273(6) Uani 1 1 d . . .
O1 O 0.01439(15) 0.58944(9) 0.42775(19) 0.0474(5) Uani 1 1 d . . .
O2 O 0.17612(14) 0.74041(7) 0.27870(17) 0.0335(4) Uani 1 1 d . . .
O3 O 0.53420(15) 0.59651(8) 0.56911(18) 0.0398(5) Uani 1 1 d . . .
P1 P 0.24284(6) 0.53561(3) 0.56598(6) 0.0289(2) 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'
O O 0.0106 0.0060 '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'
P P 0.1023 0.0942 '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
C2 C1 P1 115.48(19) . . ?
C2 C1 H1A 108.4 . . ?
P1 C1 H1A 108.4 . . ?
C2 C1 H1AB 108.4 . . ?
P1 C1 H1AB 108.4 . . ?
H1A C1 H1AB 107.5 . . ?
C3 C2 C1 111.5(2) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2AB 109.3 . . ?
C1 C2 H2AB 109.3 . . ?
H2A C2 H2AB 108.0 . . ?
C2 C3 C4 113.3(3) . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3AB 108.9 . . ?
C4 C3 H3AB 108.9 . . ?
H3A C3 H3AB 107.7 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 P1 113.53(18) . . ?
C6 C5 H5A 108.9 . . ?
P1 C5 H5A 108.9 . . ?
C6 C5 H5AB 108.9 . . ?
P1 C5 H5AB 108.9 . . ?
H5A C5 H5AB 107.7 . . ?
C7 C6 C5 113.4(2) . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6AB 108.9 . . ?
C5 C6 H6AB 108.9 . . ?
H6A C6 H6AB 107.7 . . ?
C6 C7 C8 112.7(3) . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7AB 109.0 . . ?
C8 C7 H7AB 109.0 . . ?
H7A C7 H7AB 107.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 P1 114.28(18) . . ?
C10 C9 H9A 108.7 . . ?
P1 C9 H9A 108.7 . . ?
C10 C9 H9AB 108.7 . . ?
P1 C9 H9AB 108.7 . . ?
H9A C9 H9AB 107.6 . . ?
C11 C10 C9 113.7(2) . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 C12 114.3(3) . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C31 C13 C14 105.8(2) . . ?
C31 C13 P1 129.32(19) . . ?
C14 C13 P1 124.66(18) . . ?
C15 C14 C22 120.6(2) . . ?
C15 C14 C13 132.3(2) . . ?
C22 C14 C13 107.1(2) . . ?
O1 C15 C14 125.6(2) . . ?
O1 C15 C16 120.7(2) . . ?
C14 C15 C16 113.6(2) . . ?
C21 C16 C17 117.6(2) . . ?
C21 C16 C15 121.5(2) . . ?
C17 C16 C15 120.8(2) . . ?
C18 C17 C16 121.1(3) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 119.8(3) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C20 C19 C18 120.6(3) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 119.3(3) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
O2 C21 C20 115.0(2) . . ?
O2 C21 C16 123.4(2) . . ?
C20 C21 C16 121.5(2) . . ?
C23 C22 O2 125.3(2) . . ?
C23 C22 C14 110.2(2) . . ?
O2 C22 C14 124.5(2) . . ?
C22 C23 C31 107.1(2) . . ?
C22 C23 C24 142.3(2) . . ?
C31 C23 C24 110.6(2) . . ?
C25 C24 C29 120.0(2) . . ?
C25 C24 C23 133.6(2) . . ?
C29 C24 C23 106.4(2) . . ?
C24 C25 C26 118.3(3) . . ?
C24 C25 H25 120.9 . . ?
C26 C25 H25 120.9 . . ?
C27 C26 C25 121.2(2) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C26 C27 C28 120.1(2) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C29 C28 C27 118.7(2) . . ?
C29 C28 H28 120.6 . . ?
C27 C28 H28 120.6 . . ?
C28 C29 C24 121.7(2) . . ?
C28 C29 C30 127.8(2) . . ?
C24 C29 C30 110.5(2) . . ?
O3 C30 C31 131.2(2) . . ?
O3 C30 C29 124.0(2) . . ?
C31 C30 C29 104.7(2) . . ?
C23 C31 C13 109.9(2) . . ?
C23 C31 C30 107.8(2) . . ?
C13 C31 C30 142.2(2) . . ?
C21 O2 C22 116.27(19) . . ?
C13 P1 C1 109.16(12) . . ?
C13 P1 C9 110.89(12) . . ?
C1 P1 C9 109.01(13) . . ?
C13 P1 C5 110.73(11) . . ?
C1 P1 C5 107.91(12) . . ?
C9 P1 C5 109.08(12) . . ?
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
C1 C2 1.538(3) . ?
C1 P1 1.792(3) . ?
C1 H1A 0.9900 . ?
C1 H1AB 0.9900 . ?
C2 C3 1.518(4) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C4 1.518(4) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.525(4) . ?
C5 P1 1.802(2) . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
C6 C7 1.511(4) . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 C8 1.514(4) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.516(3) . ?
C9 P1 1.798(3) . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 C11 1.494(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.507(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C31 1.420(3) . ?
C13 C14 1.434(3) . ?
C13 P1 1.766(2) . ?
C14 C15 1.422(3) . ?
C14 C22 1.426(3) . ?
C15 O1 1.245(3) . ?
C15 C16 1.485(4) . ?
C16 C21 1.394(3) . ?
C16 C17 1.399(4) . ?
C17 C18 1.371(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.394(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.364(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.390(4) . ?
C20 H20 0.9500 . ?
C21 O2 1.370(3) . ?
C22 C23 1.369(4) . ?
C22 O2 1.370(3) . ?
C23 C31 1.414(3) . ?
C23 C24 1.474(3) . ?
C24 C25 1.377(3) . ?
C24 C29 1.393(3) . ?
C25 C26 1.400(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.383(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.386(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.371(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.508(3) . ?
C30 O3 1.222(3) . ?
C30 C31 1.477(3) . ?
