#------------------------------------------------------------------------------
#$Date: 2025-08-21 04:34:05 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301843 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/74/4517459.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_4517459
loop_
_publ_author_name
'Feng, Jiaxu'
'Huang, You'
_publ_section_title
;
 Phosphine-Catalyzed Remote 1,7-Addition for Synthesis of Diene
 Carboxylates
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              3541
_journal_paper_doi               10.1021/acscatal.0c00588
_journal_year                    2020
_chemical_formula_sum            'C22 H23 N O5'
_chemical_formula_weight         381.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/8
_cell_angle_alpha                90
_cell_angle_beta                 98.41(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.199(3)
_cell_length_b                   17.845(4)
_cell_length_c                   8.5547(17)
_cell_measurement_reflns_used    4568
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9424
_cell_measurement_theta_min      1.5596
_cell_volume                     1993.3(8)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            23485
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.866
_diffrn_reflns_theta_min         2.283
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4740
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0488
_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)+(0.0611P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1211
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3165
_reflns_number_total             4740
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c00588_si_002.cif
_cod_data_source_block           R20180327B1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        1993.2(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4517459
_shelx_shelxl_version_number     2014/8
_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
loop_
_space_group_symop_operation_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_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 0.81771(8) 0.23859(6) 0.82786(11) 0.0331(3) Uani 1 1 d . . . . .
O2 O 1.06948(11) 0.20180(7) 0.16990(15) 0.0594(4) Uani 1 1 d . . . . .
O3 O 1.06293(9) 0.09852(6) 0.01961(13) 0.0426(3) Uani 1 1 d . . . . .
O4 O 0.35099(10) 0.42593(7) 0.93183(14) 0.0525(4) Uani 1 1 d . . . . .
O5 O 0.31046(8) 0.30572(6) 0.96574(13) 0.0415(3) Uani 1 1 d . . . . .
N1 N 0.77473(10) 0.17594(7) 1.04328(14) 0.0284(3) Uani 1 1 d D . . . .
C1 C 0.72778(11) 0.10791(8) 1.07370(17) 0.0273(3) Uani 1 1 d . . . . .
C2 C 0.69989(12) 0.08292(9) 1.21422(17) 0.0340(4) Uani 1 1 d . . . . .
H2 H 0.7132 0.1119 1.3081 0.041 Uiso 1 1 calc R U . . .
C3 C 0.65160(13) 0.01377(9) 1.2129(2) 0.0402(4) Uani 1 1 d . . . . .
H3 H 0.6312 -0.0049 1.3075 0.048 Uiso 1 1 calc R U . . .
C4 C 0.63275(14) -0.02842(10) 1.0763(2) 0.0430(4) Uani 1 1 d . . . . .
H4 H 0.5998 -0.0757 1.0784 0.052 Uiso 1 1 calc R U . . .
C5 C 0.66148(13) -0.00245(9) 0.93533(19) 0.0364(4) Uani 1 1 d . . . . .
H5 H 0.6486 -0.0316 0.8415 0.044 Uiso 1 1 calc R U . . .
C6 C 0.70897(11) 0.06638(8) 0.93504(17) 0.0262(3) Uani 1 1 d . . . . .
C7 C 0.74766(11) 0.10949(8) 0.80302(15) 0.0240(3) Uani 1 1 d . . . . .
C8 C 0.78461(11) 0.18282(8) 0.88822(16) 0.0261(3) Uani 1 1 d . . . . .
C9 C 0.83852(12) 0.06719(8) 0.74763(18) 0.0299(3) Uani 1 1 d . . . . .
H9A H 0.8897 0.0562 0.8414 0.036 Uiso 1 1 calc R U . . .
H9B H 0.8131 0.0186 0.7016 0.036 Uiso 1 1 calc R U . . .
C10 C 0.89098(11) 0.10759(9) 0.62921(17) 0.0309(4) Uani 1 1 d . . . . .
H10 H 0.9115 0.1579 0.6520 0.037 Uiso 1 1 calc R U . . .
C11 C 0.91113(11) 0.07804(9) 0.49354(18) 0.0304(4) Uani 1 1 d . . . . .
H11 H 0.8895 0.0282 0.4679 0.037 Uiso 1 1 calc R U . . .
C12 C 0.96466(11) 0.11886(9) 0.38383(17) 0.0318(4) Uani 1 1 d . . . . .
H12 H 0.9845 0.1690 0.4105 0.038 Uiso 1 1 calc R U . . .
C13 C 0.98818(11) 0.09169(9) 0.24867(18) 0.0329(4) Uani 1 1 d . . . . .
H13 H 0.9689 0.0419 0.2179 0.039 Uiso 1 1 calc R U . . .
C14 C 1.04334(12) 0.13755(10) 0.14686(18) 0.0356(4) Uani 1 1 d . . . . .
C15 C 1.12044(15) 0.13798(11) -0.0863(2) 0.0524(5) Uani 1 1 d . . . . .
H15A H 1.0826 0.1828 -0.1270 0.079 Uiso 1 1 calc R U . . .
H15B H 1.1304 0.1051 -0.1746 0.079 Uiso 1 1 calc R U . . .
H15C H 1.1872 0.1527 -0.0290 0.079 Uiso 1 1 calc R U . . .
C16 C 0.66258(11) 0.12682(9) 0.66318(16) 0.0285(3) Uani 1 1 d . . . . .
H16A H 0.6887 0.1630 0.5909 0.034 Uiso 1 1 calc R U . . .
H16B H 0.6435 0.0802 0.6032 0.034 Uiso 1 1 calc R U . . .
C17 C 0.57003(11) 0.15880(9) 0.72142(17) 0.0309(4) Uani 1 1 d . . . . .
H17 H 0.5247 0.1245 0.7605 0.037 Uiso 1 1 calc R U . . .
C18 C 0.54582(12) 0.23117(9) 0.72309(17) 0.0316(4) Uani 1 1 d . . . . .
H18 H 0.5848 0.2657 0.6719 0.038 Uiso 1 1 calc R U . . .
C19 C 0.46284(12) 0.25956(9) 0.79932(17) 0.0320(4) Uani 1 1 d . . . . .
H19 H 0.4199 0.2239 0.8397 0.038 Uiso 1 1 calc R U . . .
C20 C 0.44205(12) 0.33180(9) 0.81724(18) 0.0357(4) Uani 1 1 d . . . . .
H20 H 0.4802 0.3676 0.7678 0.043 Uiso 1 1 calc R U . . .
C21 C 0.36406(12) 0.35982(9) 0.90834(17) 0.0344(4) Uani 1 1 d . . . . .
C22 C 0.23481(14) 0.33076(10) 1.0606(2) 0.0487(5) Uani 1 1 d . . . . .
H22A H 0.2686 0.3592 1.1515 0.073 Uiso 1 1 calc R U . . .
H22B H 0.2000 0.2872 1.0979 0.073 Uiso 1 1 calc R U . . .
H22C H 0.1846 0.3628 0.9966 0.073 Uiso 1 1 calc R U . . .
H1 H 0.7949(12) 0.2107(8) 1.1131(16) 0.043(5) Uiso 1 1 d 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'
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
C14 O3 C15 115.72(13) . . ?
C21 O5 C22 115.48(13) . . ?
C8 N1 C1 111.55(12) . . ?
C8 N1 H1 122.7(11) . . ?
C1 N1 H1 125.8(11) . . ?
C2 C1 C6 122.24(14) . . ?
C2 C1 N1 128.39(14) . . ?
C6 C1 N1 109.35(12) . . ?
C1 C2 C3 117.39(15) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C4 C3 C2 121.14(14) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.78(16) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 118.59(15) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 119.86(13) . . ?
C5 C6 C7 131.01(13) . . ?
C1 C6 C7 109.13(12) . . ?
C6 C7 C8 101.32(11) . . ?
C6 C7 C16 113.08(12) . . ?
C8 C7 C16 109.84(11) . . ?
C6 C7 C9 109.94(11) . . ?
C8 C7 C9 110.65(12) . . ?
C16 C7 C9 111.57(11) . . ?
O1 C8 N1 125.03(13) . . ?
O1 C8 C7 126.53(13) . . ?
N1 C8 C7 108.44(12) . . ?
C10 C9 C7 115.40(12) . . ?
C10 C9 H9A 108.4 . . ?
C7 C9 H9A 108.4 . . ?
C10 C9 H9B 108.4 . . ?
C7 C9 H9B 108.4 . . ?
H9A C9 H9B 107.5 . . ?
C11 C10 C9 124.71(14) . . ?
C11 C10 H10 117.6 . . ?
C9 C10 H10 117.6 . . ?
C10 C11 C12 122.77(15) . . ?
C10 C11 H11 118.6 . . ?
C12 C11 H11 118.6 . . ?
C13 C12 C11 125.19(15) . . ?
C13 C12 H12 117.4 . . ?
C11 C12 H12 117.4 . . ?
C12 C13 C14 120.82(15) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
O2 C14 O3 122.62(14) . . ?
O2 C14 C13 126.15(14) . . ?
O3 C14 C13 111.23(14) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C7 110.72(11) . . ?
C17 C16 H16A 109.5 . . ?
C7 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C7 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C18 C17 C16 125.59(14) . . ?
C18 C17 H17 117.2 . . ?
C16 C17 H17 117.2 . . ?
C17 C18 C19 122.93(15) . . ?
C17 C18 H18 118.5 . . ?
C19 C18 H18 118.5 . . ?
C20 C19 C18 125.00(15) . . ?
C20 C19 H19 117.5 . . ?
C18 C19 H19 117.5 . . ?
C19 C20 C21 124.31(15) . . ?
C19 C20 H20 117.8 . . ?
C21 C20 H20 117.8 . . ?
O4 C21 O5 123.20(14) . . ?
O4 C21 C20 123.17(15) . . ?
O5 C21 C20 113.61(14) . . ?
O5 C22 H22A 109.5 . . ?
O5 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O5 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 C8 1.2304(16) . ?
O2 C14 1.205(2) . ?
O3 C14 1.3488(18) . ?
O3 C15 1.4471(18) . ?
O4 C21 1.2133(18) . ?
O5 C21 1.3324(18) . ?
O5 C22 1.4464(19) . ?
N1 C8 1.3573(18) . ?
N1 C1 1.4045(19) . ?
N1 H1 0.875(9) . ?
C1 C2 1.3816(19) . ?
C1 C6 1.390(2) . ?
C2 C3 1.388(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.5155(18) . ?
C7 C8 1.542(2) . ?
C7 C16 1.547(2) . ?
C7 C9 1.5487(19) . ?
C9 C10 1.4935(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.336(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.4508(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.332(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.464(2) . ?
C13 H13 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.498(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.331(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.446(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.332(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.467(2) . ?
C20 H20 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
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
N1 H1 O1 0.875(9) 2.031(10) 2.8585(16) 157.5(15) 4_566
C22 H22B O2 0.98 2.45 3.395(2) 163.3 1_456
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
C8 N1 C1 C2 -176.14(15) . . . . ?
C8 N1 C1 C6 2.30(17) . . . . ?
C6 C1 C2 C3 0.0(2) . . . . ?
N1 C1 C2 C3 178.27(15) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C1 0.4(2) . . . . ?
C4 C5 C6 C7 -179.33(15) . . . . ?
C2 C1 C6 C5 -0.4(2) . . . . ?
N1 C1 C6 C5 -178.94(14) . . . . ?
C2 C1 C6 C7 179.43(13) . . . . ?
N1 C1 C6 C7 0.87(16) . . . . ?
C5 C6 C7 C8 176.59(16) . . . . ?
C1 C6 C7 C8 -3.19(15) . . . . ?
C5 C6 C7 C16 59.1(2) . . . . ?
C1 C6 C7 C16 -120.68(13) . . . . ?
C5 C6 C7 C9 -66.3(2) . . . . ?
C1 C6 C7 C9 113.88(14) . . . . ?
C1 N1 C8 O1 175.64(14) . . . . ?
C1 N1 C8 C7 -4.40(16) . . . . ?
C6 C7 C8 O1 -175.50(14) . . . . ?
C16 C7 C8 O1 -55.68(19) . . . . ?
C9 C7 C8 O1 67.94(19) . . . . ?
C6 C7 C8 N1 4.53(15) . . . . ?
C16 C7 C8 N1 124.36(12) . . . . ?
C9 C7 C8 N1 -112.02(13) . . . . ?
C6 C7 C9 C10 -173.90(13) . . . . ?
C8 C7 C9 C10 -62.81(17) . . . . ?
C16 C7 C9 C10 59.80(17) . . . . ?
C7 C9 C10 C11 -129.78(16) . . . . ?
C9 C10 C11 C12 -178.39(14) . . . . ?
C10 C11 C12 C13 178.80(16) . . . . ?
C11 C12 C13 C14 -179.45(14) . . . . ?
C15 O3 C14 O2 1.8(2) . . . . ?
C15 O3 C14 C13 -177.97(14) . . . . ?
C12 C13 C14 O2 -2.2(3) . . . . ?
C12 C13 C14 O3 177.55(14) . . . . ?
C6 C7 C16 C17 48.22(16) . . . . ?
C8 C7 C16 C17 -64.15(15) . . . . ?
C9 C7 C16 C17 172.78(12) . . . . ?
C7 C16 C17 C18 99.68(17) . . . . ?
C16 C17 C18 C19 -171.73(14) . . . . ?
C17 C18 C19 C20 173.18(16) . . . . ?
C18 C19 C20 C21 -173.70(14) . . . . ?
C22 O5 C21 O4 -0.5(2) . . . . ?
C22 O5 C21 C20 178.15(14) . . . . ?
C19 C20 C21 O4 174.97(17) . . . . ?
C19 C20 C21 O5 -3.6(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168346570
