#------------------------------------------------------------------------------
#$Date: 2023-09-05 22:05:53 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286030 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/93/1569335.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_1569335
loop_
_publ_author_name
'Li, Can'
'Zhou, Zhengnan'
'Ma, Shengming'
_publ_section_title
;
 A Pd-catalyzed highly selective three-component protocol for
 trisubstituted allenes.
;
_journal_issue                   28
_journal_name_full               'Chemical science'
_journal_page_first              7709
_journal_page_last               7715
_journal_paper_doi               10.1039/d3sc01849k
_journal_volume                  14
_journal_year                    2023
_chemical_formula_sum            'C25 H22 O4'
_chemical_formula_weight         386.42
_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   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2022-08-23 deposited with the CCDC.	2023-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                115.168(3)
_cell_angle_beta                 93.669(4)
_cell_angle_gamma                93.606(4)
_cell_formula_units_Z            2
_cell_length_a                   8.2186(9)
_cell_length_b                   10.7453(13)
_cell_length_c                   12.2370(14)
_cell_measurement_reflns_used    9865
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      55.007
_cell_measurement_theta_min      4.992
_cell_volume                     971.2(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22564
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         2.953
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.053(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3771
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0425P)²+0.3007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0943
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3428
_reflns_number_total             3771
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc01849k2.cif
_cod_data_source_block           mo_d8v21709_0m
_cod_depositor_comments          'Adding full bibliography for 1569335.cif.'
_cod_original_cell_volume        971.20(19)
_cod_database_code               1569335
_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   0.982
_shelx_estimated_absorpt_t_max   0.989
_shelxl_version_number           2013-4
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.09617(11) 0.42474(9) 0.63091(8) 0.0388(2) Uani 1 1 d . . . . .
O2 O 0.31412(11) 0.49846(9) 0.56441(7) 0.0345(2) Uani 1 1 d . . . . .
O3 O 0.28288(18) 0.83481(10) 0.90374(9) 0.0636(4) Uani 1 1 d . . . . .
O4 O 0.15422(11) 0.74522(9) 0.71735(8) 0.0407(2) Uani 1 1 d . . . . .
C1 C 0.32007(13) 0.09982(11) 0.53329(10) 0.0270(2) Uani 1 1 d . . . . .
H1 H 0.2713 0.0972 0.5998 0.032 Uiso 1 1 calc R U . . .
C2 C 0.25636(13) 0.00479(11) 0.41410(10) 0.0267(2) Uani 1 1 d . . . . .
C3 C 0.12535(14) -0.09808(12) 0.39052(11) 0.0329(3) Uani 1 1 d . . . . .
H3 H 0.0810 -0.1078 0.4558 0.039 Uiso 1 1 calc R U . . .
C4 C 0.06232(15) -0.18351(13) 0.27441(12) 0.0377(3) Uani 1 1 d . . . . .
H4 H -0.0250 -0.2509 0.2605 0.045 Uiso 1 1 calc R U . . .
C5 C 0.12752(16) -0.17113(13) 0.17525(11) 0.0370(3) Uani 1 1 d . . . . .
H5 H 0.0808 -0.2279 0.0958 0.044 Uiso 1 1 calc R U . . .
C6 C 0.25797(15) -0.07725(13) 0.19431(11) 0.0338(3) Uani 1 1 d . . . . .
H6 H 0.3029 -0.0718 0.1275 0.041 Uiso 1 1 calc R U . . .
C7 C 0.32717(14) 0.01274(11) 0.31396(10) 0.0278(3) Uani 1 1 d . . . . .
C8 C 0.46432(15) 0.10989(12) 0.33717(11) 0.0319(3) Uani 1 1 d . . . . .
H8 H 0.5137 0.1146 0.2717 0.038 Uiso 1 1 calc R U . . .
C9 C 0.52621(15) 0.19684(12) 0.45287(11) 0.0311(3) Uani 1 1 d . . . . .
H9 H 0.6196 0.2585 0.4661 0.037 Uiso 1 1 calc R U . . .
C10 C 0.45071(13) 0.19519(11) 0.55389(10) 0.0266(2) Uani 1 1 d . . . . .
C11 C 0.51512(14) 0.29840(11) 0.67740(10) 0.0283(3) Uani 1 1 d . . . . .
H11 H 0.6283 0.3260 0.6916 0.034 Uiso 1 1 calc R U . . .
C12 C 0.42722(13) 0.35429(11) 0.76834(10) 0.0261(2) Uani 1 1 d . . . . .
C13 C 0.33877(13) 0.41736(11) 0.85822(9) 0.0239(2) Uani 1 1 d . . . . .
C14 C 0.30326(13) 0.36205(11) 0.94794(10) 0.0252(2) Uani 1 1 d . . . . .
C15 C 0.35068(16) 0.23397(12) 0.93275(11) 0.0351(3) Uani 1 1 d . . . . .
H15 H 0.4057 0.1824 0.8653 0.042 Uiso 1 1 calc R U . . .
C16 C 0.31817(19) 0.18145(14) 1.01530(13) 0.0439(3) Uani 1 1 d . . . . .
H16 H 0.3513 0.0949 1.0036 0.053 Uiso 1 1 calc R U . . .
C17 C 0.23689(17) 0.25581(14) 1.11517(12) 0.0408(3) Uani 1 1 d . . . . .
H17 H 0.2145 0.2199 1.1711 0.049 Uiso 1 1 calc R U . . .
C18 C 0.18899(15) 0.38298(14) 1.13200(11) 0.0363(3) Uani 1 1 d . . . . .
H18 H 0.1340 0.4339 1.1997 0.044 Uiso 1 1 calc R U . . .
C19 C 0.22176(14) 0.43598(12) 1.04925(10) 0.0304(3) Uani 1 1 d . . . . .
H19 H 0.1887 0.5227 1.0615 0.036 Uiso 1 1 calc R U . . .
C20 C 0.26769(14) 0.54998(11) 0.87358(10) 0.0268(2) Uani 1 1 d . . . . .
H20A H 0.3123 0.6237 0.9524 0.032 Uiso 1 1 calc R U . . .
H20B H 0.1488 0.5373 0.8746 0.032 Uiso 1 1 calc R U . . .
C21 C 0.30261(14) 0.59608(11) 0.77457(10) 0.0262(2) Uani 1 1 d . . . . .
H21 H 0.4227 0.6034 0.7712 0.031 Uiso 1 1 calc R U . . .
C22 C 0.22384(14) 0.49497(11) 0.65007(10) 0.0272(3) Uani 1 1 d . . . . .
C23 C 0.24376(19) 0.41908(16) 0.44084(11) 0.0476(4) Uani 1 1 d . . . . .
H23A H 0.3207 0.4249 0.3859 0.071 Uiso 1 1 calc R U . . .
H23B H 0.1432 0.4556 0.4276 0.071 Uiso 1 1 calc R U . . .
H23C H 0.2200 0.3233 0.4259 0.071 Uiso 1 1 calc R U . . .
C24 C 0.24548(15) 0.73869(12) 0.80773(10) 0.0312(3) Uani 1 1 d . . . . .
C25 C 0.09944(18) 0.87873(14) 0.74003(16) 0.0494(4) Uani 1 1 d . . . . .
H25A H 0.0198 0.8689 0.6741 0.074 Uiso 1 1 calc R U . . .
H25B H 0.1924 0.9420 0.7454 0.074 Uiso 1 1 calc R U . . .
H25C H 0.0494 0.9147 0.8157 0.074 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 0.0033 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'
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
C22 O2 C23 115.96(10) . . ?
C24 O4 C25 116.25(10) . . ?
C10 C1 C2 121.68(10) . . ?
C10 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C3 C2 C1 122.76(10) . . ?
C3 C2 C7 118.51(11) . . ?
C1 C2 C7 118.73(10) . . ?
C4 C3 C2 121.00(11) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 120.40(12) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.19(11) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.83(11) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C2 118.66(10) . . ?
C8 C7 C6 122.41(11) . . ?
C2 C7 C6 118.94(11) . . ?
C9 C8 C7 121.19(10) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 120.66(11) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C1 C10 C9 118.94(10) . . ?
C1 C10 C11 122.43(10) . . ?
C9 C10 C11 118.63(10) . . ?
C12 C11 C10 125.24(10) . . ?
C12 C11 H11 117.4 . . ?
C10 C11 H11 117.4 . . ?
C11 C12 C13 176.35(12) . . ?
C12 C13 C14 121.93(10) . . ?
C12 C13 C20 120.67(10) . . ?
C14 C13 C20 117.40(9) . . ?
C15 C14 C19 117.97(11) . . ?
C15 C14 C13 120.55(10) . . ?
C19 C14 C13 121.48(10) . . ?
C16 C15 C14 121.08(12) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 120.29(12) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 119.57(12) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.21(12) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 120.88(11) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C13 C20 C21 114.19(9) . . ?
C13 C20 H20A 108.7 . . ?
C21 C20 H20A 108.7 . . ?
C13 C20 H20B 108.7 . . ?
C21 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
C22 C21 C24 110.20(9) . . ?
C22 C21 C20 112.89(9) . . ?
C24 C21 C20 109.59(9) . . ?
C22 C21 H21 108.0 . . ?
C24 C21 H21 108.0 . . ?
C20 C21 H21 108.0 . . ?
O1 C22 O2 124.81(11) . . ?
O1 C22 C21 124.99(10) . . ?
O2 C22 C21 110.16(9) . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O3 C24 O4 123.86(11) . . ?
O3 C24 C21 123.37(11) . . ?
O4 C24 C21 112.74(10) . . ?
O4 C25 H25A 109.5 . . ?
O4 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O4 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
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
O1 C22 1.2017(14) . ?
O2 C22 1.3342(14) . ?
O2 C23 1.4414(15) . ?
O3 C24 1.1930(15) . ?
O4 C24 1.3255(15) . ?
O4 C25 1.4479(15) . ?
C1 C10 1.3688(16) . ?
C1 C2 1.4187(16) . ?
C1 H1 0.9400 . ?
C2 C3 1.4155(16) . ?
C2 C7 1.4218(16) . ?
C3 C4 1.3662(17) . ?
C3 H3 0.9400 . ?
C4 C5 1.4102(19) . ?
C4 H4 0.9400 . ?
C5 C6 1.3614(19) . ?
C5 H5 0.9400 . ?
C6 C7 1.4221(16) . ?
C6 H6 0.9400 . ?
C7 C8 1.4142(17) . ?
C8 C9 1.3635(17) . ?
C8 H8 0.9400 . ?
C9 C10 1.4245(16) . ?
C9 H9 0.9400 . ?
C10 C11 1.4807(15) . ?
C11 C12 1.3077(16) . ?
C11 H11 0.9400 . ?
C12 C13 1.3144(16) . ?
C13 C14 1.4894(15) . ?
C13 C20 1.5160(15) . ?
C14 C15 1.3927(16) . ?
C14 C19 1.3972(16) . ?
C15 C16 1.3823(18) . ?
C15 H15 0.9400 . ?
C16 C17 1.385(2) . ?
C16 H16 0.9400 . ?
C17 C18 1.3796(19) . ?
C17 H17 0.9400 . ?
C18 C19 1.3887(17) . ?
C18 H18 0.9400 . ?
C19 H19 0.9400 . ?
C20 C21 1.5273(15) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C21 C22 1.5159(15) . ?
C21 C24 1.5229(15) . ?
C21 H21 0.9900 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 H25C 0.9700 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C23 H23B O1 0.97 2.64 3.5946(18) 169.1 2_566
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
_geom_torsion_publ_flag
C10 C1 C2 C3 177.60(10) . . . . ?
C10 C1 C2 C7 -2.21(16) . . . . ?
C1 C2 C3 C4 176.88(11) . . . . ?
C7 C2 C3 C4 -3.30(17) . . . . ?
C2 C3 C4 C5 0.30(18) . . . . ?
C3 C4 C5 C6 2.45(19) . . . . ?
C4 C5 C6 C7 -2.09(18) . . . . ?
C3 C2 C7 C8 -176.27(10) . . . . ?
C1 C2 C7 C8 3.55(15) . . . . ?
C3 C2 C7 C6 3.59(16) . . . . ?
C1 C2 C7 C6 -176.58(10) . . . . ?
C5 C6 C7 C8 178.91(11) . . . . ?
C5 C6 C7 C2 -0.95(17) . . . . ?
C2 C7 C8 C9 -1.46(17) . . . . ?
C6 C7 C8 C9 178.68(11) . . . . ?
C7 C8 C9 C10 -2.06(18) . . . . ?
C2 C1 C10 C9 -1.26(16) . . . . ?
C2 C1 C10 C11 177.77(10) . . . . ?
C8 C9 C10 C1 3.44(17) . . . . ?
C8 C9 C10 C11 -175.63(10) . . . . ?
C1 C10 C11 C12 -32.42(17) . . . . ?
C9 C10 C11 C12 146.61(12) . . . . ?
C12 C13 C14 C15 -5.92(16) . . . . ?
C20 C13 C14 C15 173.65(10) . . . . ?
C12 C13 C14 C19 174.17(11) . . . . ?
C20 C13 C14 C19 -6.25(15) . . . . ?
C19 C14 C15 C16 0.01(18) . . . . ?
C13 C14 C15 C16 -179.89(11) . . . . ?
C14 C15 C16 C17 0.1(2) . . . . ?
C15 C16 C17 C18 -0.2(2) . . . . ?
C16 C17 C18 C19 0.1(2) . . . . ?
C17 C18 C19 C14 0.03(18) . . . . ?
C15 C14 C19 C18 -0.10(17) . . . . ?
C13 C14 C19 C18 179.80(10) . . . . ?
C12 C13 C20 C21 2.40(15) . . . . ?
C14 C13 C20 C21 -177.18(9) . . . . ?
C13 C20 C21 C22 64.10(12) . . . . ?
C13 C20 C21 C24 -172.66(9) . . . . ?
C23 O2 C22 O1 4.94(17) . . . . ?
C23 O2 C22 C21 -173.06(10) . . . . ?
C24 C21 C22 O1 -90.59(13) . . . . ?
C20 C21 C22 O1 32.31(15) . . . . ?
C24 C21 C22 O2 87.40(11) . . . . ?
C20 C21 C22 O2 -149.69(9) . . . . ?
C25 O4 C24 O3 0.13(19) . . . . ?
C25 O4 C24 C21 -177.95(10) . . . . ?
C22 C21 C24 O3 175.88(13) . . . . ?
C20 C21 C24 O3 51.06(17) . . . . ?
C22 C21 C24 O4 -6.03(14) . . . . ?
C20 C21 C24 O4 -130.84(10) . . . . ?
