#------------------------------------------------------------------------------
#$Date: 2024-10-04 07:50:01 +0300 (Fri, 04 Oct 2024) $
#$Revision: 295037 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/38/7133831.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_7133831
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 H37 O3 P'
_chemical_formula_sum            'C31 H37 O3 P'
_chemical_formula_weight         488.58
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2024-07-22 deposited with the CCDC.	2024-08-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.976(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3575(5)
_cell_length_b                   11.1326(5)
_cell_length_c                   21.2159(11)
_cell_measurement_reflns_used    6062
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.88
_cell_measurement_theta_min      2.17
_cell_volume                     2656.6(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_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  0.0721
_diffrn_reflns_av_sigmaI/netI    0.0523
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24725
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.9960
_exptl_absorpt_correction_T_min  0.9712
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4697
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0442
_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)+(0.0771P)²+0.5786P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1386
_reflns_number_gt                3726
_reflns_number_total             4697
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4cc03210a3.cif
_cod_data_source_block           d25113
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7133831
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.61034(18) 0.36705(19) 0.88591(9) 0.0319(5) Uani 1 1 d . . .
H1A H 0.6128 0.4534 0.8971 0.038 Uiso 1 1 calc R . .
H1B H 0.5258 0.3440 0.8747 0.038 Uiso 1 1 calc R . .
C2 C 0.6642(2) 0.2945(2) 0.94443(10) 0.0409(6) Uani 1 1 d . . .
H2A H 0.6507 0.2079 0.9356 0.049 Uiso 1 1 calc R . .
H2B H 0.7512 0.3082 0.9519 0.049 Uiso 1 1 calc R . .
C3 C 0.6121(2) 0.3273(2) 1.00435(11) 0.0512(6) Uani 1 1 d . . .
H3A H 0.5243 0.3233 0.9952 0.061 Uiso 1 1 calc R . .
H3B H 0.6384 0.2674 1.0378 0.061 Uiso 1 1 calc R . .
C4 C 0.6480(3) 0.4510(3) 1.02910(13) 0.0629(8) Uani 1 1 d . . .
H4A H 0.6076 0.4694 1.0659 0.094 Uiso 1 1 calc R . .
H4B H 0.6255 0.5105 0.9956 0.094 Uiso 1 1 calc R . .
H4C H 0.7343 0.4534 1.0419 0.094 Uiso 1 1 calc R . .
C5 C 0.84095(17) 0.37533(18) 0.84266(10) 0.0319(5) Uani 1 1 d . . .
H5A H 0.8735 0.3133 0.8738 0.038 Uiso 1 1 calc R . .
H5B H 0.8847 0.3701 0.8055 0.038 Uiso 1 1 calc R . .
C6 C 0.86072(19) 0.5003(2) 0.87328(11) 0.0385(5) Uani 1 1 d . . .
H6A H 0.8316 0.5620 0.8413 0.046 Uiso 1 1 calc R . .
H6B H 0.8127 0.5067 0.9087 0.046 Uiso 1 1 calc R . .
C7 C 0.9898(2) 0.5270(2) 0.89871(12) 0.0450(6) Uani 1 1 d . . .
H7A H 1.0386 0.5199 0.8637 0.054 Uiso 1 1 calc R . .
H7B H 1.0190 0.4669 0.9316 0.054 Uiso 1 1 calc R . .
C8 C 1.0043(3) 0.6527(2) 0.92741(14) 0.0625(8) Uani 1 1 d . . .
H8A H 1.0881 0.6664 0.9441 0.094 Uiso 1 1 calc R . .
H8B H 0.9560 0.6599 0.9620 0.094 Uiso 1 1 calc R . .
H8C H 0.9783 0.7125 0.8945 0.094 Uiso 1 1 calc R . .
C9 C 0.66475(18) 0.19019(17) 0.79570(10) 0.0312(5) Uani 1 1 d . . .
H9A H 0.7195 0.1685 0.7651 0.037 Uiso 1 1 calc R . .
H9B H 0.6848 0.1397 0.8341 0.037 Uiso 1 1 calc R . .
C10 C 0.5358(2) 0.1643(2) 0.76569(11) 0.0417(6) Uani 1 1 d . . .
H10A H 0.4831 0.2258 0.7806 0.050 Uiso 1 1 calc R . .
H10B H 0.5304 0.1720 0.7189 0.050 Uiso 1 1 calc R . .
C11 C 0.4912(2) 0.0411(2) 0.78121(13) 0.0526(7) Uani 1 1 d . . .
H11A H 0.4197 0.0218 0.7507 0.063 Uiso 1 1 calc R . .
H11B H 0.5530 -0.0192 0.7756 0.063 Uiso 1 1 calc R . .
C12 C 0.4607(3) 0.0313(3) 0.84784(14) 0.0708(9) Uani 1 1 d . . .
H12A H 0.4365 -0.0512 0.8557 0.106 Uiso 1 1 calc R . .
H12B H 0.3953 0.0864 0.8528 0.106 Uiso 1 1 calc R . .
H12C H 0.5305 0.0525 0.8784 0.106 Uiso 1 1 calc R . .
C13 C 0.62335(17) 0.44196(17) 0.75626(9) 0.0257(4) Uani 1 1 d . . .
C14 C 0.64760(17) 0.44193(17) 0.69059(9) 0.0261(4) Uani 1 1 d . . .
C15 C 0.72781(17) 0.37521(18) 0.65891(9) 0.0284(4) Uani 1 1 d . . .
C16 C 0.72649(18) 0.40993(18) 0.59112(10) 0.0314(5) Uani 1 1 d . . .
C17 C 0.8015(2) 0.3547(2) 0.55251(11) 0.0456(6) Uani 1 1 d . . .
H17 H 0.8537 0.2927 0.5698 0.055 Uiso 1 1 calc R . .
C18 C 0.8010(2) 0.3886(2) 0.49021(11) 0.0528(7) Uani 1 1 d . . .
H18 H 0.8523 0.3495 0.4649 0.063 Uiso 1 1 calc R . .
C19 C 0.7260(2) 0.4795(2) 0.46395(11) 0.0468(6) Uani 1 1 d . . .
H19 H 0.7260 0.5025 0.4208 0.056 Uiso 1 1 calc R . .
C20 C 0.65210(19) 0.5360(2) 0.50025(10) 0.0369(5) Uani 1 1 d . . .
H20 H 0.6006 0.5982 0.4824 0.044 Uiso 1 1 calc R . .
C21 C 0.65274(17) 0.50177(18) 0.56349(9) 0.0297(5) Uani 1 1 d . . .
C22 C 0.57442(16) 0.53172(17) 0.65830(9) 0.0254(4) Uani 1 1 d . . .
C23 C 0.50591(16) 0.58528(17) 0.69934(9) 0.0267(4) Uani 1 1 d . . .
C24 C 0.41436(17) 0.67650(17) 0.70326(10) 0.0285(4) Uani 1 1 d . . .
C25 C 0.35338(18) 0.75276(19) 0.65834(10) 0.0352(5) Uani 1 1 d . . .
H25 H 0.3689 0.7522 0.6155 0.042 Uiso 1 1 calc R . .
C26 C 0.26886(19) 0.8301(2) 0.67759(12) 0.0409(6) Uani 1 1 d . . .
H26 H 0.2266 0.8828 0.6473 0.049 Uiso 1 1 calc R . .
C27 C 0.24511(19) 0.8318(2) 0.73965(12) 0.0417(6) Uani 1 1 d . . .
H27 H 0.1869 0.8853 0.7516 0.050 Uiso 1 1 calc R . .
C28 C 0.30586(18) 0.75556(19) 0.78477(11) 0.0361(5) Uani 1 1 d . . .
H28 H 0.2897 0.7564 0.8275 0.043 Uiso 1 1 calc R . .
C29 C 0.39047(17) 0.67839(17) 0.76636(10) 0.0284(4) Uani 1 1 d . . .
C30 C 0.46916(17) 0.58925(17) 0.80797(9) 0.0273(4) Uani 1 1 d . . .
H30 H 0.4176 0.5276 0.8248 0.033 Uiso 1 1 calc R . .
C31 C 0.53707(16) 0.53090(17) 0.75938(9) 0.0249(4) Uani 1 1 d . . .
O1 O 0.79561(13) 0.29458(13) 0.68440(7) 0.0376(4) Uani 1 1 d . . .
O2 O 0.57580(12) 0.56373(12) 0.59601(6) 0.0312(3) Uani 1 1 d . . .
O3 O 0.54216(12) 0.64456(12) 0.85996(6) 0.0303(3) Uani 1 1 d . . .
H1 H 0.5989 0.6957 0.8446 0.036 Uiso 1 1 d R . .
P1 P 0.68536(4) 0.34550(5) 0.81727(2) 0.02592(17) 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'
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 113.78(14) . . ?
C2 C1 H1A 108.8 . . ?
P1 C1 H1A 108.8 . . ?
C2 C1 H1B 108.8 . . ?
P1 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
C3 C2 C1 113.09(19) . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C2 113.1(2) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
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 111.82(14) . . ?
C6 C5 H5A 109.3 . . ?
P1 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
P1 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C5 113.81(18) . . ?
C7 C6 H6A 108.8 . . ?
C5 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C6 C7 C8 111.5(2) . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
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 111.63(14) . . ?
C10 C9 H9A 109.3 . . ?
P1 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
P1 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C9 114.1(2) . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C10 113.4(2) . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
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 105.75(16) . . ?
C31 C13 P1 127.60(15) . . ?
C14 C13 P1 126.59(14) . . ?
C22 C14 C15 120.96(17) . . ?
C22 C14 C13 106.65(16) . . ?
C15 C14 C13 132.35(18) . . ?
O1 C15 C14 124.58(18) . . ?
O1 C15 C16 121.71(17) . . ?
C14 C15 C16 113.70(17) . . ?
C21 C16 C17 116.92(19) . . ?
C21 C16 C15 121.37(18) . . ?
C17 C16 C15 121.68(19) . . ?
C18 C17 C16 121.3(2) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 120.4(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 119.9(2) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 119.6(2) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
O2 C21 C20 115.33(18) . . ?
O2 C21 C16 122.90(17) . . ?
C20 C21 C16 121.76(19) . . ?
O2 C22 C23 125.33(17) . . ?
O2 C22 C14 124.47(17) . . ?
C23 C22 C14 110.14(16) . . ?
C22 C23 C31 106.94(17) . . ?
C22 C23 C24 143.33(18) . . ?
C31 C23 C24 109.74(17) . . ?
C25 C24 C29 120.14(18) . . ?
C25 C24 C23 132.54(19) . . ?
C29 C24 C23 107.31(17) . . ?
C24 C25 C26 118.4(2) . . ?
C24 C25 H25 120.8 . . ?
C26 C25 H25 120.8 . . ?
C27 C26 C25 121.5(2) . . ?
C27 C26 H26 119.3 . . ?
C25 C26 H26 119.3 . . ?
C26 C27 C28 120.3(2) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C27 C28 C29 118.8(2) . . ?
C27 C28 H28 120.6 . . ?
C29 C28 H28 120.6 . . ?
C28 C29 C24 120.80(19) . . ?
C28 C29 C30 127.72(19) . . ?
C24 C29 C30 111.47(16) . . ?
O3 C30 C31 114.53(15) . . ?
O3 C30 C29 113.37(15) . . ?
C31 C30 C29 101.35(15) . . ?
O3 C30 H30 109.1 . . ?
C31 C30 H30 109.1 . . ?
C29 C30 H30 109.1 . . ?
C13 C31 C23 110.51(17) . . ?
C13 C31 C30 139.44(18) . . ?
C23 C31 C30 110.03(16) . . ?
C22 O2 C21 116.57(15) . . ?
C30 O3 H1 110.0 . . ?
C13 P1 C9 112.15(10) . . ?
C13 P1 C1 109.18(9) . . ?
C9 P1 C1 105.94(10) . . ?
C13 P1 C5 112.59(10) . . ?
C9 P1 C5 109.92(10) . . ?
C1 P1 C5 106.70(10) . . ?
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 1.535(3) . ?
C1 P1 1.802(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.520(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.510(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.539(3) . ?
C5 P1 1.805(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.519(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.526(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.541(3) . ?
C9 P1 1.796(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.514(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.505(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C31 1.401(3) . ?
C13 C14 1.457(3) . ?
C13 P1 1.7527(19) . ?
C14 C22 1.415(3) . ?
C14 C15 1.415(3) . ?
C15 O1 1.255(2) . ?
C15 C16 1.488(3) . ?
C16 C21 1.398(3) . ?
C16 C17 1.403(3) . ?
C17 C18 1.374(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.368(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.394(3) . ?
C20 H20 0.9500 . ?
C21 O2 1.372(2) . ?
C22 O2 1.371(2) . ?
C22 C23 1.381(3) . ?
C23 C31 1.410(3) . ?
C23 C24 1.464(3) . ?
C24 C25 1.388(3) . ?
C24 C29 1.403(3) . ?
C25 C26 1.392(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.380(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.389(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.385(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.531(3) . ?
C30 O3 1.424(2) . ?
C30 C31 1.517(3) . ?
C30 H30 1.0000 . ?
O3 H1 0.9507 . ?
