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#$Date: 2025-08-20 21:19:29 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301836 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/59/4305992.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_4305992
loop_
_publ_author_name
'Roberto Pattacini'
'Günter Margraf'
'Abdelatif Messaoudi'
'Nicola Oberbeckmann-Winter'
'Pierre Braunstein'
_publ_contact_author_address
;Laboratoire de Chimie de Coordination
CNRS-Université Louis Pasteur
Institut Le Bel - 4 rue Blaise Pascal
67070 Strasbourg Cedex - France
;
_publ_contact_author_email       braunst@chimie.u-strasbg.fr
_publ_contact_author_fax         +33(0)390241322
_publ_contact_author_name        'Dr. Pierre Braunstein'
_publ_contact_author_phone       +33(0)390241308
_publ_section_title
;
Formation of P-C Bonds under Unexpectedly Mild Conditions. Phosphoryl
Migration and Metal Coordination of Diphenylphosphinomethyl-oxazolines and
-thiazolines
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              9886
_journal_page_last               9897
_journal_paper_doi               10.1021/ic800934h
_journal_volume                  47
_journal_year                    2008
_chemical_formula_moiety         'C16 H16 N P S'
_chemical_formula_sum            'C16 H16 N P S'
_chemical_formula_weight         285.33
_chemical_name_common            margraf_mono
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 109.814(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6510(4)
_cell_length_b                   8.0670(3)
_cell_length_c                   16.3080(7)
_cell_measurement_reflns_used    2653
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.131
_cell_measurement_theta_min      0.998
_cell_volume                     1442.02(10)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Platon
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Shelxs-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0896
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6126
_diffrn_reflns_theta_full        29.15
_diffrn_reflns_theta_max         29.15
_diffrn_reflns_theta_min         1.86
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3861
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1020
_refine_ls_R_factor_gt           0.0618
_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)+(0.0160P)²+0.8434P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1061
_reflns_number_gt                2818
_reflns_number_total             3861
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic800934h_si_001_1.cif
_cod_data_source_block           compound1th
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4305992
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6296(2) 0.0995(3) 0.58990(16) 0.0377(6) Uani 1 1 d . . .
H1A H 0.6195 0.0124 0.5470 0.045 Uiso 1 1 calc R . .
H1B H 0.7157 0.1073 0.6239 0.045 Uiso 1 1 calc R . .
C2 C 0.5869(3) 0.2629(4) 0.5433(2) 0.0690(10) Uani 1 1 d . . .
H2A H 0.5549 0.2458 0.4808 0.083 Uiso 1 1 calc R . .
H2B H 0.6543 0.3406 0.5565 0.083 Uiso 1 1 calc R . .
C3 C 0.48436(18) 0.1653(2) 0.64883(13) 0.0223(4) Uani 1 1 d . . .
C4 C 0.40840(18) 0.1600(2) 0.70629(13) 0.0236(4) Uani 1 1 d . . .
H4A H 0.4244 0.2585 0.7425 0.028 Uiso 1 1 calc R . .
H4B H 0.4320 0.0645 0.7445 0.028 Uiso 1 1 calc R . .
C5 C 0.22432(17) -0.0697(2) 0.60901(13) 0.0201(4) Uani 1 1 d . . .
C6 C 0.27354(19) -0.2010(2) 0.66573(14) 0.0266(5) Uani 1 1 d . . .
H6 H 0.3196 -0.1790 0.7235 0.032 Uiso 1 1 calc R . .
C7 C 0.2547(2) -0.3629(3) 0.63713(15) 0.0302(5) Uani 1 1 d . . .
H7 H 0.2887 -0.4492 0.6754 0.036 Uiso 1 1 calc R . .
C8 C 0.1854(2) -0.3969(3) 0.55183(15) 0.0287(5) Uani 1 1 d . . .
H8 H 0.1728 -0.5061 0.5327 0.034 Uiso 1 1 calc R . .
C9 C 0.1346(2) -0.2691(3) 0.49473(14) 0.0292(5) Uani 1 1 d . . .
H9 H 0.0872 -0.2922 0.4373 0.035 Uiso 1 1 calc R . .
C10 C 0.15449(18) -0.1060(3) 0.52328(13) 0.0245(4) Uani 1 1 d . . .
H10 H 0.1207 -0.0200 0.4846 0.029 Uiso 1 1 calc R . .
C11 C 0.18025(18) 0.1393(2) 0.73299(13) 0.0203(4) Uani 1 1 d . . .
C12 C 0.0663(2) 0.0654(3) 0.71735(14) 0.0310(5) Uani 1 1 d . . .
H12 H 0.0283 0.0123 0.6645 0.037 Uiso 1 1 calc R . .
C13 C 0.0092(2) 0.0698(3) 0.77889(15) 0.0352(5) Uani 1 1 d . . .
H13 H -0.0667 0.0202 0.7670 0.042 Uiso 1 1 calc R . .
C14 C 0.0642(2) 0.1475(3) 0.85800(15) 0.0315(5) Uani 1 1 d . . .
H14 H 0.0252 0.1519 0.8991 0.038 Uiso 1 1 calc R . .
C15 C 0.1773(2) 0.2181(3) 0.87520(15) 0.0332(5) Uani 1 1 d . . .
H15 H 0.2156 0.2686 0.9288 0.040 Uiso 1 1 calc R . .
C16 C 0.23484(19) 0.2147(3) 0.81345(14) 0.0288(5) Uani 1 1 d . . .
H16 H 0.3112 0.2637 0.8261 0.035 Uiso 1 1 calc R . .
N1 N 0.56133(17) 0.0557(2) 0.64776(12) 0.0320(4) Uani 1 1 d . . .
P1 P 0.24205(5) 0.14794(6) 0.64367(3) 0.02077(14) Uani 1 1 d . . .
S1 S 0.47046(6) 0.34151(7) 0.58106(4) 0.03785(17) Uani 1 1 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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
N1 C1 C2 111.93(18) . . ?
N1 C1 H1A 109.2 . . ?
C2 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C1 C2 S1 107.11(17) . . ?
C1 C2 H2A 110.3 . . ?
S1 C2 H2A 110.3 . . ?
C1 C2 H2B 110.3 . . ?
S1 C2 H2B 110.3 . . ?
H2A C2 H2B 108.5 . . ?
N1 C3 C4 124.28(19) . . ?
N1 C3 S1 117.87(16) . . ?
C4 C3 S1 117.79(15) . . ?
C3 C4 P1 112.69(14) . . ?
C3 C4 H4A 109.1 . . ?
P1 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
P1 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C10 C5 C6 118.45(18) . . ?
C10 C5 P1 118.53(14) . . ?
C6 C5 P1 122.96(15) . . ?
C7 C6 C5 120.8(2) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C8 C7 C6 120.1(2) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 120.2(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C10 119.8(2) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C5 120.72(19) . . ?
C9 C10 H10 119.6 . . ?
C5 C10 H10 119.6 . . ?
C16 C11 C12 117.49(19) . . ?
C16 C11 P1 123.83(15) . . ?
C12 C11 P1 118.43(15) . . ?
C13 C12 C11 121.2(2) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 120.4(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 119.2(2) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 120.7(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 121.0(2) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
C3 N1 C1 112.44(18) . . ?
C11 P1 C5 100.08(9) . . ?
C11 P1 C4 100.51(9) . . ?
C5 P1 C4 101.92(9) . . ?
C3 S1 C2 90.61(11) . . ?
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
C1 N1 1.469(3) . ?
C1 C2 1.518(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 S1 1.785(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N1 1.264(2) . ?
C3 C4 1.492(3) . ?
C3 S1 1.774(2) . ?
C4 P1 1.862(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C10 1.390(3) . ?
C5 C6 1.395(3) . ?
C5 P1 1.8346(19) . ?
C6 C7 1.379(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.379(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.381(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C16 1.389(3) . ?
C11 C12 1.397(3) . ?
C11 P1 1.832(2) . ?
C12 C13 1.380(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.387(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660809
2 PubChem 101437412
