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#$Date: 2025-08-20 15:05:43 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301829 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/06/41/4064110.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_4064110
loop_
_publ_author_name
'Hu, Dan-Fu'
'Weng, Chia-Ming'
'Hong, Fung-E'
_publ_section_title
;
 Preparation of New Buchwald-Type Secondary Phosphine Oxide Ligands and
 Applications in Suzuki−Miyaura Reactions
;
_journal_issue                   5
_journal_name_full               Organometallics
_journal_page_first              1139
_journal_paper_doi               10.1021/om101132t
_journal_volume                  30
_journal_year                    2011
_chemical_formula_moiety         'C13 H15 N2 O P'
_chemical_formula_sum            'C13 H15 N2 O P'
_chemical_formula_weight         246.24
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.735(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1942(7)
_cell_length_b                   12.4860(12)
_cell_length_c                   14.8755(13)
_cell_measurement_reflns_used    4946
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.996
_cell_measurement_theta_min      3.130
_cell_volume                     1336.1(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7328
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.9536
_exptl_absorpt_correction_T_min  0.8314
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   empirical
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             520
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          0.57
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1500P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1624
_refine_ls_wR_factor_ref         0.1725
_reflns_number_gt                2338
_reflns_number_total             2622
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om101132t_si_001.cif
_cod_data_source_block           hong165m
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4064110
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
P1 P 0.03823(5) 0.05592(3) 0.18424(3) 0.0467(2) Uani 1 1 d .
C1 C -0.15097(19) 0.23995(12) 0.17946(9) 0.0434(4) Uani 1 1 d .
O1 O -0.0237(2) -0.05360(10) 0.15979(11) 0.0715(5) Uani 1 1 d .
C9 C -0.0502(2) 0.11155(13) 0.28773(11) 0.0469(4) Uani 1 1 d .
C2 C -0.0633(2) 0.16649(13) 0.12195(10) 0.0471(4) Uani 1 1 d .
C8 C -0.1474(3) 0.16993(18) 0.41254(12) 0.0682(6) Uani 1 1 d .
H8A H -0.1717 0.1744 0.4737 0.082 Uiso 1 1 calc R
C3 C -0.0670(3) 0.18644(18) 0.03056(12) 0.0652(5) Uani 1 1 d .
H3A H -0.0106 0.1393 -0.0091 0.078 Uiso 1 1 calc R
C4 C -0.1555(3) 0.2775(2) -0.00122(13) 0.0804(7) Uani 1 1 d .
H4A H -0.1592 0.2908 -0.0627 0.097 Uiso 1 1 calc R
C5 C -0.2391(3) 0.34940(18) 0.05685(13) 0.0715(6) Uani 1 1 d .
H5A H -0.2960 0.4106 0.0339 0.086 Uiso 1 1 calc R
C6 C -0.2385(2) 0.33105(14) 0.14848(11) 0.0546(4) Uani 1 1 d .
H6A H -0.2952 0.3785 0.1878 0.066 Uiso 1 1 calc R
N2 N -0.0506(2) 0.08651(14) 0.37324(10) 0.0614(4) Uani 1 1 d .
C7 C -0.2025(2) 0.24428(16) 0.35117(12) 0.0578(5) Uani 1 1 d .
H7A H -0.2680 0.3072 0.3615 0.069 Uiso 1 1 calc R
N1 N -0.14009(17) 0.20597(10) 0.27067(8) 0.0439(3) Uani 1 1 d .
C10 C 0.2905(3) 0.07233(16) 0.18850(15) 0.0615(5) Uani 1 1 d .
C11 C 0.3673(4) -0.0019(2) 0.2634(2) 0.1074(10) Uani 1 1 d .
H11A H 0.5000 0.0053 0.2672 0.161 Uiso 1 1 calc R
H11B H 0.3356 -0.0748 0.2496 0.161 Uiso 1 1 calc R
H11C H 0.3138 0.0179 0.3198 0.161 Uiso 1 1 calc R
C12 C 0.3388(3) 0.18786(18) 0.21226(18) 0.0762(6) Uani 1 1 d .
H12A H 0.4715 0.1961 0.2146 0.114 Uiso 1 1 calc R
H12B H 0.2880 0.2053 0.2698 0.114 Uiso 1 1 calc R
H12C H 0.2874 0.2349 0.1674 0.114 Uiso 1 1 calc R
C13 C 0.3682(4) 0.0435(2) 0.0955(2) 0.1025(10) Uani 1 1 d .
H13A H 0.5009 0.0517 0.0965 0.154 Uiso 1 1 calc R
H13B H 0.3150 0.0902 0.0508 0.154 Uiso 1 1 calc R
H13C H 0.3370 -0.0294 0.0812 0.154 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 0.0033 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'
P P 0.1023 0.0942 '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
O1 P1 C2 117.37(9)
O1 P1 C9 117.04(8)
C2 P1 C9 89.92(7)
O1 P1 C10 114.03(9)
C2 P1 C10 109.05(8)
C9 P1 C10 106.69(8)
C6 C1 C2 122.75(15)
C6 C1 N1 125.80(13)
C2 C1 N1 111.44(14)
N2 C9 N1 112.30(14)
N2 C9 P1 137.62(13)
N1 C9 P1 110.09(11)
C3 C2 C1 118.49(16)
C3 C2 P1 130.02(14)
C1 C2 P1 111.49(11)
C7 C8 N2 111.96(16)
C7 C8 H8A 124.0
N2 C8 H8A 124.0
C2 C3 C4 119.16(18)
C2 C3 H3A 120.4
C4 C3 H3A 120.4
C5 C4 C3 121.34(18)
C5 C4 H4A 119.3
C3 C4 H4A 119.3
C4 C5 C6 120.70(19)
C4 C5 H5A 119.7
C6 C5 H5A 119.7
C1 C6 C5 117.56(16)
C1 C6 H6A 121.2
C5 C6 H6A 121.2
C9 N2 C8 103.73(16)
C8 C7 N1 104.65(16)
C8 C7 H7A 127.7
N1 C7 H7A 127.7
C9 N1 C7 107.36(14)
C9 N1 C1 117.02(12)
C7 N1 C1 135.61(15)
C12 C10 C11 108.8(2)
C12 C10 C13 110.17(19)
C11 C10 C13 112.1(2)
C12 C10 P1 109.73(13)
C11 C10 P1 107.67(15)
C13 C10 P1 108.30(17)
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C10 C12 H12A 109.5
C10 C12 H12B 109.5
H12A C12 H12B 109.5
C10 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C10 C13 H13A 109.5
C10 C13 H13B 109.5
H13A C13 H13B 109.5
C10 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O1 1.4819(12)
P1 C2 1.8114(17)
P1 C9 1.8118(16)
P1 C10 1.8267(19)
C1 C6 1.377(2)
C1 C2 1.409(2)
C1 N1 1.4228(19)
C9 N2 1.310(2)
C9 N1 1.367(2)
C2 C3 1.382(2)
C8 C7 1.358(3)
C8 N2 1.386(2)
C8 H8A 0.9300
C3 C4 1.383(3)
C3 H3A 0.9300
C4 C5 1.388(3)
C4 H4A 0.9300
C5 C6 1.382(2)
C5 H5A 0.9300
C6 H6A 0.9300
C7 N1 1.370(2)
C7 H7A 0.9300
C10 C12 1.524(3)
C10 C11 1.545(3)
C10 C13 1.542(3)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139097594
