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#$Date: 2025-08-20 17:12:52 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301832 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/47/4104702.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_4104702
loop_
_publ_author_name
'Liang Yin'
'Motomu Kanai'
'Masakatsu Shibasaki'
_publ_section_title
;
 Nucleophile Generation via Decarboxylation: Asymmetric Construction of
 Contiguous Trisubstituted and Quaternary Stereocenters through a
 Cu(I)-Catalyzed Decarboxylative Mannich-Type Reaction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9610
_journal_page_last               9611
_journal_paper_doi               10.1021/ja9036675
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H27 N2 O P '
_chemical_formula_sum            'C30 H27 N2 O P'
_chemical_formula_weight         462.53
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 109.6941(19)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   10.6583(4)
_cell_length_b                   9.8999(4)
_cell_length_c                   12.4412(7)
_cell_measurement_reflns_used    5056
_cell_measurement_temperature    93.1
_cell_measurement_theta_max      68.1
_cell_measurement_theta_min      3.8
_cell_volume                     1235.96(10)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku & RAC 2007)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'CrystalStructure (Rigaku & RAC 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.073
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12061
_diffrn_reflns_theta_full        68.18
_diffrn_reflns_theta_max         68.18
_exptl_absorpt_coefficient_mu    1.173
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       needle
_exptl_crystal_F_000             488.00
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.48
_refine_diff_density_min         -0.42
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1606 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3968
_refine_ls_R_factor_gt           0.0581
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0541P)²+0.1342P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1390
_reflns_number_gt                3121
_reflns_number_total             3968
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja9036675_si_001.cif
_cod_data_source_block           '_#1'
_cod_original_cell_volume        1235.95(10)
_cod_original_formula_sum        'C30 H27 N2 O P '
_cod_database_code               4104702
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
P1 P 0.50413(10) 0.69501(10) 0.53107(8) 0.0267(3) Uani 1 1 d .
O1 O 0.5058(3) 0.8409(3) 0.5027(2) 0.0297(6) Uani 1 1 d .
N1 N 0.4479(3) 0.6041(3) 0.4149(3) 0.0237(7) Uani 1 1 d .
H1N H 0.4530 0.5171 0.4242 0.028 Uiso 1 1 d .
N2 N 0.6118(4) 0.6414(4) 0.2283(3) 0.0381(9) Uani 1 1 d .
C1 C 0.3368(4) 0.6552(4) 0.3174(3) 0.0265(9) Uani 1 1 d .
H1 H 0.3419 0.7560 0.3216 0.032 Uiso 1 1 calc R
C2 C 0.3571(4) 0.6135(4) 0.2013(3) 0.0262(9) Uani 1 1 d .
C3 C 0.3207(4) 0.4638(4) 0.1724(3) 0.0308(10) Uani 1 1 d .
H3A H 0.3669 0.4089 0.2408 0.037 Uiso 1 1 calc R
H3B H 0.2237 0.4531 0.1562 0.037 Uiso 1 1 calc R
C4 C 0.3543(5) 0.4076(5) 0.0735(4) 0.0357(10) Uani 1 1 d .
H4 H 0.4410 0.4248 0.0710 0.043 Uiso 1 1 calc R
C5 C 0.2727(5) 0.3365(5) -0.0099(4) 0.0429(11) Uani 1 1 d .
H5A H 0.1852 0.3172 -0.0104 0.052 Uiso 1 1 calc R
H5B H 0.3011 0.3041 -0.0699 0.052 Uiso 1 1 calc R
C6 C 0.1999(4) 0.6165(4) 0.3216(3) 0.0266(9) Uani 1 1 d .
C7 C 0.0971(4) 0.7101(5) 0.2868(3) 0.0329(10) Uani 1 1 d .
H7 H 0.1120 0.7952 0.2578 0.040 Uiso 1 1 calc R
C8 C -0.0262(4) 0.6812(5) 0.2939(3) 0.0379(10) Uani 1 1 d .
H8 H -0.0950 0.7470 0.2710 0.046 Uiso 1 1 calc R
C9 C -0.0512(4) 0.5564(5) 0.3343(3) 0.0364(11) Uani 1 1 d .
H9 H -0.1368 0.5357 0.3379 0.044 Uiso 1 1 calc R
C10 C 0.0517(4) 0.4631(5) 0.3693(4) 0.0334(10) Uani 1 1 d .
H10 H 0.0365 0.3777 0.3975 0.040 Uiso 1 1 calc R
C11 C 0.1753(4) 0.4925(4) 0.3638(3) 0.0308(10) Uani 1 1 d .
H11 H 0.2448 0.4276 0.3890 0.037 Uiso 1 1 calc R
C12 C 0.5012(4) 0.6289(4) 0.2193(3) 0.0285(9) Uani 1 1 d .
C13 C 0.2803(4) 0.7127(5) 0.1063(3) 0.0278(9) Uani 1 1 d .
C14 C 0.1486(4) 0.6915(5) 0.0394(3) 0.0332(9) Uani 1 1 d .
H14 H 0.1052 0.6105 0.0482 0.040 Uiso 1 1 calc R
C15 C 0.0794(5) 0.7868(5) -0.0399(4) 0.0374(11) Uani 1 1 d .
H15 H -0.0111 0.7708 -0.0845 0.045 Uiso 1 1 calc R
C16 C 0.1403(5) 0.9045(5) -0.0548(4) 0.0400(11) Uani 1 1 d .
H16 H 0.0923 0.9689 -0.1100 0.048 Uiso 1 1 calc R
C17 C 0.2714(5) 0.9288(4) 0.0109(4) 0.0376(11) Uani 1 1 d .
H17 H 0.3140 1.0101 0.0015 0.045 Uiso 1 1 calc R
C18 C 0.3409(4) 0.8328(5) 0.0911(3) 0.0332(10) Uani 1 1 d .
H18 H 0.4310 0.8495 0.1361 0.040 Uiso 1 1 calc R
C19 C 0.6685(4) 0.6299(4) 0.6042(3) 0.0261(9) Uani 1 1 d .
C20 C 0.7578(4) 0.6211(4) 0.5451(4) 0.0337(10) Uani 1 1 d .
H20 H 0.7279 0.6393 0.4655 0.040 Uiso 1 1 calc R
C21 C 0.8897(4) 0.5860(4) 0.6003(4) 0.0343(10) Uani 1 1 d .
H21 H 0.9499 0.5803 0.5589 0.041 Uiso 1 1 calc R
C22 C 0.9333(4) 0.5594(4) 0.7164(4) 0.0346(10) Uani 1 1 d .
H22 H 1.0238 0.5363 0.7550 0.041 Uiso 1 1 calc R
C23 C 0.8456(4) 0.5663(5) 0.7760(4) 0.0361(11) Uani 1 1 d .
H23 H 0.8755 0.5467 0.8554 0.043 Uiso 1 1 calc R
C24 C 0.7144(4) 0.6019(4) 0.7207(3) 0.0299(9) Uani 1 1 d .
H24 H 0.6547 0.6073 0.7626 0.036 Uiso 1 1 calc R
C25 C 0.4097(4) 0.6700(4) 0.6251(3) 0.0272(9) Uani 1 1 d .
C26 C 0.3880(4) 0.5405(5) 0.6607(3) 0.0311(10) Uani 1 1 d .
H26 H 0.4148 0.4630 0.6290 0.037 Uiso 1 1 calc R
C27 C 0.3274(4) 0.5263(5) 0.7425(3) 0.0341(10) Uani 1 1 d .
H27 H 0.3134 0.4386 0.7675 0.041 Uiso 1 1 calc R
C28 C 0.2871(4) 0.6389(5) 0.7880(4) 0.0382(11) Uani 1 1 d .
H28 H 0.2475 0.6282 0.8454 0.046 Uiso 1 1 calc R
C29 C 0.3038(4) 0.7660(5) 0.7509(4) 0.0365(10) Uani 1 1 d .
H29 H 0.2743 0.8430 0.7812 0.044 Uiso 1 1 calc R
C30 C 0.3642(4) 0.7808(5) 0.6689(3) 0.0333(10) Uani 1 1 d .
H30 H 0.3746 0.8687 0.6423 0.040 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.031 0.018
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.049 0.032
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
P P 0.295 0.434
;
International Tables for Crystallography
(1992, 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
O1 P1 N1 110.77(16)
O1 P1 C19 112.34(17)
N1 P1 C19 104.73(17)
O1 P1 C25 109.95(17)
N1 P1 C25 112.38(17)
C19 P1 C25 106.53(17)
C1 N1 P1 119.6(3)
N1 C1 C6 113.6(3)
N1 C1 C2 110.0(3)
C6 C1 C2 113.0(3)
C12 C2 C13 107.8(3)
C12 C2 C3 107.5(3)
C13 C2 C3 114.0(3)
C12 C2 C1 106.7(3)
C13 C2 C1 109.4(3)
C3 C2 C1 111.1(3)
C4 C3 C2 115.8(3)
C5 C4 C3 124.7(4)
C7 C6 C11 118.4(4)
C7 C6 C1 119.0(4)
C11 C6 C1 122.5(4)
C8 C7 C6 120.8(4)
C7 C8 C9 120.7(4)
C10 C9 C8 118.5(4)
C11 C10 C9 120.9(4)
C10 C11 C6 120.7(4)
N2 C12 C2 177.1(4)
C14 C13 C18 118.0(4)
C14 C13 C2 122.1(4)
C18 C13 C2 119.8(3)
C15 C14 C13 120.9(4)
C16 C15 C14 120.7(4)
C15 C16 C17 119.8(4)
C16 C17 C18 119.4(4)
C13 C18 C17 121.3(4)
C20 C19 C24 118.4(4)
C20 C19 P1 118.6(3)
C24 C19 P1 122.6(3)
C21 C20 C19 121.1(4)
C20 C21 C22 119.5(4)
C23 C22 C21 120.2(4)
C22 C23 C24 120.1(4)
C23 C24 C19 120.7(4)
C30 C25 C26 119.0(4)
C30 C25 P1 119.6(3)
C26 C25 P1 121.3(3)
C27 C26 C25 119.6(4)
C28 C27 C26 120.3(4)
C29 C28 C27 120.5(4)
C28 C29 C30 119.3(4)
C25 C30 C29 121.1(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O1 1.488(3)
P1 N1 1.636(3)
P1 C19 1.799(4)
P1 C25 1.800(4)
N1 C1 1.470(5)
N2 C12 1.152(5)
C1 C6 1.526(5)
C1 C2 1.586(5)
C2 C12 1.484(6)
C2 C13 1.542(5)
C2 C3 1.543(5)
C3 C4 1.500(5)
C4 C5 1.312(6)
C6 C7 1.389(5)
C6 C11 1.395(6)
C7 C8 1.377(5)
C8 C9 1.393(6)
C9 C10 1.387(6)
C10 C11 1.373(5)
C13 C14 1.386(5)
C13 C18 1.395(6)
C14 C15 1.385(6)
C15 C16 1.377(6)
C16 C17 1.382(6)
C17 C18 1.396(6)
C19 C20 1.388(5)
C19 C24 1.393(5)
C20 C21 1.385(6)
C21 C22 1.386(6)
C22 C23 1.376(6)
C23 C24 1.380(5)
C25 C30 1.383(5)
C25 C26 1.401(6)
C26 C27 1.384(5)
C27 C28 1.383(6)
C28 C29 1.372(6)
C29 C30 1.386(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139115565
