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#$Date: 2024-07-05 21:01:34 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293283 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/99/7159939.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_7159939
loop_
_publ_author_name
'Liu, Xian'
'Hao, Liqiang'
'Wang, Yangyang'
'Yu, Xiao'
'Yang, Zhaoziyuan'
'Liu, Yiping'
'Ji, Yafei'
_publ_section_title
;
 Cu₂O-catalyzed cascade phosphinylation/cyclization of
 2'-aminochalcones for the synthesis of hemi-indigo derivatives.
;
_journal_issue                   21
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4249
_journal_page_last               4253
_journal_paper_doi               10.1039/d4ob00594e
_journal_volume                  22
_journal_year                    2024
_chemical_formula_sum            'C29 H24 N O4 P'
_chemical_formula_weight         481.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2024-04-24 deposited with the CCDC.	2024-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.6320(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.3847(4)
_cell_length_b                   17.7511(5)
_cell_length_c                   18.5322(5)
_cell_measurement_reflns_used    9148
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      75.0377
_cell_measurement_theta_min      5.3772
_cell_volume                     5136.8(2)
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  Quest
_diffrn_measurement_method       'phi and omi'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            58205
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.430
_diffrn_reflns_theta_min         3.770
_exptl_absorpt_coefficient_mu    1.229
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_correction_T_min  0.73
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         4667
_refine_ls_number_restraints     187
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0743P)²+5.5477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1447
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4164
_reflns_number_total             4667
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00594e2.cif
_cod_data_source_block           rs814_330_55_1_0m_a_sq
_cod_depositor_comments          'Adding full bibliography for 7159939.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7159939
_shelx_shelxl_version_number     2019/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.837
_shelx_estimated_absorpt_t_max   0.941
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.8706(8) 0.3450(12) 0.3602(13) 0.046(3) Uani 0.56(4) 1 d D U P A 3
O3 O 0.8198(9) 0.3682(10) 0.6369(8) 0.042(2) Uani 0.56(4) 1 d . U P A 3
O4 O 0.6643(9) 0.3386(10) 0.6044(10) 0.0369(19) Uani 0.56(4) 1 d . U P A 3
C28 C 0.9119(10) 0.3710(12) 0.6601(8) 0.055(3) Uani 0.56(4) 1 d . U P A 3
H28A H 0.933413 0.373393 0.714348 0.082 Uiso 0.56(4) 1 calc R U P A 3
H28B H 0.930100 0.414854 0.638823 0.082 Uiso 0.56(4) 1 calc R U P A 3
H28C H 0.933653 0.326646 0.642643 0.082 Uiso 0.56(4) 1 calc R U P A 3
C29 C 0.5791(14) 0.3172(13) 0.5932(14) 0.046(3) Uani 0.56(4) 1 d . U P A 3
H29A H 0.568115 0.314651 0.641135 0.070 Uiso 0.56(4) 1 calc R U P A 3
H29B H 0.569106 0.268755 0.569134 0.070 Uiso 0.56(4) 1 calc R U P A 3
H29C H 0.541522 0.353670 0.561510 0.070 Uiso 0.56(4) 1 calc R U P A 3
O2A O 0.8668(10) 0.3636(12) 0.3581(15) 0.036(2) Uani 0.44(4) 1 d D U P A 4
O3A O 0.8220(12) 0.3899(12) 0.6388(11) 0.044(2) Uani 0.44(4) 1 d . U P A 4
O4A O 0.6580(14) 0.3572(13) 0.6023(14) 0.045(3) Uani 0.44(4) 1 d . U P A 4
C28A C 0.9104(15) 0.3987(16) 0.6595(13) 0.063(4) Uani 0.44(4) 1 d . U P A 4
H28D H 0.931455 0.413183 0.711738 0.094 Uiso 0.44(4) 1 calc R U P A 4
H28E H 0.924468 0.436959 0.628611 0.094 Uiso 0.44(4) 1 calc R U P A 4
H28F H 0.936349 0.351911 0.652268 0.094 Uiso 0.44(4) 1 calc R U P A 4
C29A C 0.5692(19) 0.3343(15) 0.5903(18) 0.048(4) Uani 0.44(4) 1 d . U P A 4
H29D H 0.557875 0.332223 0.638147 0.072 Uiso 0.44(4) 1 calc R U P A 4
H29E H 0.559893 0.285553 0.566892 0.072 Uiso 0.44(4) 1 calc R U P A 4
H29F H 0.531543 0.370263 0.558048 0.072 Uiso 0.44(4) 1 calc R U P A 4
P1 P 0.61471(3) 0.29129(3) 0.15621(3) 0.03394(17) Uani 1 1 d . . . . .
O1 O 0.53689(9) 0.30984(10) 0.17807(9) 0.0452(4) Uani 1 1 d . . . . .
N1 N 0.65142(10) 0.32029(10) 0.33628(9) 0.0371(4) Uani 1 1 d . . . . .
H1 H 0.598543 0.310751 0.312906 0.045 Uiso 1 1 calc R U . . .
C1 C 0.62467(13) 0.34695(12) 0.07769(12) 0.0376(5) Uani 1 1 d . . . . .
C2 C 0.67040(16) 0.32414(14) 0.02958(13) 0.0479(5) Uani 1 1 d . . . . .
H2 H 0.690462 0.274914 0.031923 0.058 Uiso 1 1 calc R U . . .
C3 C 0.68640(19) 0.37415(16) -0.02190(15) 0.0615(7) Uani 1 1 d . . . . .
H3 H 0.717445 0.358406 -0.053670 0.074 Uiso 1 1 calc R U . . .
C4 C 0.6567(2) 0.44683(16) -0.02627(17) 0.0672(8) Uani 1 1 d . . . . .
H4 H 0.667969 0.480550 -0.060453 0.081 Uiso 1 1 calc R U . . .
C5 C 0.6102(2) 0.46922(15) 0.02018(19) 0.0701(8) Uani 1 1 d . . . . .
H5 H 0.589323 0.518230 0.016782 0.084 Uiso 1 1 calc R U . . .
C6 C 0.59387(16) 0.42019(14) 0.07199(15) 0.0526(6) Uani 1 1 d . . . . .
H6 H 0.562172 0.436293 0.103088 0.063 Uiso 1 1 calc R U . . .
C7 C 0.61909(13) 0.19361(12) 0.13010(12) 0.0378(5) Uani 1 1 d . . . . .
C8 C 0.65949(16) 0.14044(14) 0.18409(14) 0.0509(6) Uani 1 1 d . . . . .
H8 H 0.689429 0.155650 0.232968 0.061 Uiso 1 1 calc R U . . .
C9 C 0.6552(2) 0.06499(16) 0.16515(19) 0.0692(8) Uani 1 1 d . . . . .
H9 H 0.681980 0.029517 0.201557 0.083 Uiso 1 1 calc R U . . .
C10 C 0.6117(2) 0.04193(16) 0.09308(19) 0.0687(8) Uani 1 1 d . . . . .
H10 H 0.609390 -0.008988 0.080809 0.082 Uiso 1 1 calc R U . . .
C11 C 0.5720(2) 0.09355(15) 0.03934(16) 0.0623(7) Uani 1 1 d . . . . .
H11 H 0.542913 0.077900 -0.009606 0.075 Uiso 1 1 calc R U . . .
C12 C 0.57494(15) 0.16908(14) 0.05783(13) 0.0472(5) Uani 1 1 d . . . . .
H12 H 0.546935 0.203968 0.021260 0.057 Uiso 1 1 calc R U . . .
C13 C 0.71296(13) 0.31136(12) 0.22984(11) 0.0365(4) Uani 1 1 d . . . . .
C14 C 0.71593(12) 0.32362(11) 0.30241(11) 0.0341(4) Uani 1 1 d . . . . .
C15 C 0.79754(12) 0.34438(12) 0.36558(11) 0.0356(4) Uani 1 1 d D . . . .
C16 C 0.77152(12) 0.35005(11) 0.43269(11) 0.0339(4) Uani 1 1 d . . . . .
C17 C 0.68438(12) 0.33461(11) 0.41366(11) 0.0318(4) Uani 1 1 d . . . . .
C18 C 0.79139(8) 0.31681(9) 0.20481(9) 0.0432(5) Uani 1 1 d G U . . .
C19 C 0.83721(10) 0.25216(8) 0.19974(10) 0.0565(6) Uani 1 1 d G U . . .
H19 H 0.819969 0.205693 0.213196 0.068 Uiso 1 1 calc R U . . .
C20 C 0.90878(10) 0.25695(12) 0.17455(11) 0.0763(9) Uani 1 1 d G U . . .
H20 H 0.939431 0.213694 0.171152 0.092 Uiso 1 1 calc R U . . .
C21 C 0.93454(10) 0.32640(14) 0.15443(12) 0.0852(11) Uani 1 1 d G U . . .
H21 H 0.982431 0.329602 0.137578 0.102 Uiso 1 1 calc R U . . .
C22 C 0.88873(13) 0.39105(11) 0.15951(12) 0.0870(11) Uani 1 1 d G U . . .
H22 H 0.905970 0.437510 0.146048 0.104 Uiso 1 1 calc R U . . .
C23 C 0.81716(11) 0.38625(8) 0.18470(11) 0.0640(7) Uani 1 1 d G U . . .
H23 H 0.786508 0.429511 0.188092 0.077 Uiso 1 1 calc R U . . .
C24 C 0.82049(13) 0.36507(12) 0.50737(11) 0.0375(5) Uani 1 1 d . . . . .
H24 H 0.878658 0.375614 0.519159 0.045 Uiso 1 1 calc R U . . .
C25 C 0.78111(13) 0.36393(13) 0.56253(11) 0.0379(5) Uani 1 1 d . . . . .
C26 C 0.69199(13) 0.34733(12) 0.54336(11) 0.0369(5) Uani 1 1 d . . . . .
C27 C 0.64279(13) 0.33329(12) 0.46912(11) 0.0351(4) Uani 1 1 d . . . . .
H27 H 0.584439 0.323419 0.456918 0.042 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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
C25 O3 C28 116.0(12) . . ?
C26 O4 C29 118.7(15) . . ?
C28A O3A C25 116.1(16) . . ?
C26 O4A C29A 118(2) . . ?
O1 P1 C13 113.12(9) . . ?
O1 P1 C1 113.11(10) . . ?
C13 P1 C1 102.93(10) . . ?
O1 P1 C7 113.10(10) . . ?
C13 P1 C7 107.07(10) . . ?
C1 P1 C7 106.77(9) . . ?
C14 N1 C17 110.34(16) . . ?
C6 C1 C2 118.7(2) . . ?
C6 C1 P1 117.03(17) . . ?
C2 C1 P1 123.78(17) . . ?
C3 C2 C1 120.5(2) . . ?
C4 C3 C2 120.3(3) . . ?
C5 C4 C3 119.4(2) . . ?
C4 C5 C6 121.1(3) . . ?
C5 C6 C1 120.1(2) . . ?
C12 C7 C8 118.6(2) . . ?
C12 C7 P1 120.58(17) . . ?
C8 C7 P1 120.53(18) . . ?
C9 C8 C7 120.0(2) . . ?
C10 C9 C8 120.5(3) . . ?
C11 C10 C9 120.2(3) . . ?
C10 C11 C12 119.8(3) . . ?
C11 C12 C7 120.9(2) . . ?
C14 C13 C18 121.60(18) . . ?
C14 C13 P1 122.75(16) . . ?
C18 C13 P1 115.60(13) . . ?
C13 C14 N1 130.04(19) . . ?
C13 C14 C15 124.09(18) . . ?
N1 C14 C15 105.87(16) . . ?
O2 C15 C16 128.4(11) . . ?
O2A C15 C16 127.2(13) . . ?
O2 C15 C14 125.8(11) . . ?
O2A C15 C14 126.9(13) . . ?
C16 C15 C14 105.04(16) . . ?
C17 C16 C24 121.72(18) . . ?
C17 C16 C15 108.54(17) . . ?
C24 C16 C15 129.69(18) . . ?
C16 C17 N1 110.18(17) . . ?
C16 C17 C27 120.64(18) . . ?
N1 C17 C27 129.16(18) . . ?
C19 C18 C23 120.0 . . ?
C19 C18 C13 119.99(13) . . ?
C23 C18 C13 119.98(13) . . ?
C18 C19 C20 120.0 . . ?
C21 C20 C19 120.0 . . ?
C20 C21 C22 120.0 . . ?
C21 C22 C23 120.0 . . ?
C22 C23 C18 120.0 . . ?
C25 C24 C16 118.60(19) . . ?
O3 C25 C24 126.1(6) . . ?
O3 C25 C26 113.6(6) . . ?
C24 C25 C26 119.85(18) . . ?
C24 C25 O3A 123.0(8) . . ?
C26 C25 O3A 116.5(8) . . ?
O4 C26 C27 124.6(6) . . ?
O4A C26 C27 123.7(9) . . ?
O4 C26 C25 113.2(6) . . ?
O4A C26 C25 113.9(9) . . ?
C27 C26 C25 121.80(18) . . ?
C26 C27 C17 117.39(18) . . ?
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
O2 C15 1.232(9) . ?
O3 C25 1.334(15) . ?
O3 C28 1.439(19) . ?
O4 C26 1.348(18) . ?
O4 C29 1.40(3) . ?
O2A C15 1.232(11) . ?
O3A C28A 1.39(3) . ?
O3A C25 1.445(18) . ?
O4A C26 1.38(3) . ?
O4A C29A 1.46(4) . ?
P1 O1 1.4871(15) . ?
P1 C13 1.803(2) . ?
P1 C1 1.807(2) . ?
P1 C7 1.807(2) . ?
N1 C14 1.384(3) . ?
N1 C17 1.394(2) . ?
C1 C6 1.387(3) . ?
C1 C2 1.387(3) . ?
C2 C3 1.385(4) . ?
C3 C4 1.373(4) . ?
C4 C5 1.370(4) . ?
C5 C6 1.381(4) . ?
C7 C12 1.385(3) . ?
C7 C8 1.389(3) . ?
C8 C9 1.381(4) . ?
C9 C10 1.372(5) . ?
C10 C11 1.365(4) . ?
C11 C12 1.381(4) . ?
C13 C14 1.349(3) . ?
C13 C18 1.496(2) . ?
C14 C15 1.532(3) . ?
C15 C16 1.435(3) . ?
C16 C17 1.390(3) . ?
C16 C24 1.399(3) . ?
C17 C27 1.395(3) . ?
C18 C19 1.3900 . ?
C18 C23 1.3900 . ?
C19 C20 1.3900 . ?
C20 C21 1.3900 . ?
C21 C22 1.3900 . ?
C22 C23 1.3900 . ?
C24 C25 1.364(3) . ?
C25 C26 1.425(3) . ?
C26 C27 1.390(3) . ?
