#------------------------------------------------------------------------------
#$Date: 2016-08-07 12:20:11 +0300 (Sun, 07 Aug 2016) $
#$Revision: 185511 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/03/92/7039265.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_7039265
loop_
_publ_author_name
'Zablocka, Maria'
'Oshovsky, Gennady'
'Duhayon, Carine'
'Ladeira, Sonia'
'Caminade, Anne-Marie'
'Mignani, Serge'
'Majoral, Jean-Pierre'
_publ_section_title
;
 Thiazoyl phosphines. Design, reactivity, and complexation.
;
_journal_issue                   23
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              9695
_journal_page_last               9703
_journal_paper_doi               10.1039/c6dt01106c
_journal_volume                  45
_journal_year                    2016
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C27 H23 N3 O3 P2 S'
_chemical_formula_sum            'C27 H23 N3 O3 P2 S'
_chemical_formula_weight         531.48
_chemical_name_systematic
;
 ?
;
_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_date             2016-04-21T17:31:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2016-05-02 deposited with the CCDC.
2016-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 126.095(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2093(12)
_cell_length_b                   12.8509(12)
_cell_length_c                   19.0029(14)
_cell_measurement_reflns_used    9882
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      30.54
_cell_measurement_theta_min      2.48
_cell_measurement_wavelength     0.71073
_cell_volume                     2606.6(4)
_computing_cell_refinement       'APEX2 and SAINT'
_computing_data_collection       APEX2
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       ω-φ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            24526
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.69
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.4
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         4755
_refine_ls_number_restraints     144
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.032
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0401P)²+1.5235P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0907
_reflns_number_gt                4225
_reflns_number_total             4755
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6dt01106c1.cif
_cod_data_source_block           cpd21
_cod_depositor_comments
'Adding full bibliography for 7039261--7039268.cif.'
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               7039265
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
S1 S 1.11108(4) 0.44064(3) 0.73190(3) 0.02728(12) Uani 1 1 d . . .
P1 P 0.74248(4) 0.67150(3) 0.74017(3) 0.01951(12) Uani 1 1 d . . .
P2 P 0.98391(4) 0.58297(3) 0.79155(3) 0.01908(11) Uani 1 1 d . . .
O1 O 0.64628(12) 0.72840(10) 0.64891(8) 0.0300(3) Uani 1 1 d . . .
O3 O 0.75020(13) 0.73417(10) 0.80779(8) 0.0317(3) Uani 1 1 d . . .
N3 N 0.86106(13) 0.64902(12) 0.74309(9) 0.0253(3) Uani 1 1 d . . .
N1 N 0.98441(14) 0.53668(11) 0.58353(9) 0.0236(3) Uani 1 1 d . . .
N2 N 1.12520(16) 0.41236(12) 0.59727(10) 0.0308(4) Uani 1 1 d D . .
C13 C 0.64317(16) 0.71016(15) 0.57484(11) 0.0278(4) Uani 1 1 d . . .
C14 C 0.61547(18) 0.61392(17) 0.53646(12) 0.0357(4) Uani 1 1 d . . .
H14 H 0.6035 0.556 0.5618 0.043 Uiso 1 1 calc R . .
C15 C 0.6053(2) 0.6028(2) 0.45963(14) 0.0482(6) Uani 1 1 d . . .
H15 H 0.5863 0.5365 0.4324 0.058 Uiso 1 1 calc R . .
C16 C 0.6223(2) 0.6865(2) 0.42271(14) 0.0545(7) Uani 1 1 d . . .
H16 H 0.6141 0.6782 0.3699 0.065 Uiso 1 1 calc R . .
C17 C 0.6510(2) 0.7819(2) 0.46233(15) 0.0542(7) Uani 1 1 d . . .
H17 H 0.6637 0.8397 0.4371 0.065 Uiso 1 1 calc R . .
C18 C 0.66189(19) 0.79485(18) 0.53911(14) 0.0417(5) Uani 1 1 d . . .
H18 H 0.6819 0.861 0.5666 0.05 Uiso 1 1 calc R . .
O2 O 0.68073(13) 0.56066(10) 0.73136(9) 0.0317(3) Uani 1 1 d D A .
C7 C 0.60360(18) 0.54086(15) 0.75792(13) 0.0324(4) Uani 1 1 d D . .
C8 C 0.4958(9) 0.5893(7) 0.7301(9) 0.0422(15) Uani 0.59 1 d PDU A 1
H8 H 0.4686 0.6468 0.6916 0.051 Uiso 0.59 1 calc PR A 1
C9 C 0.4229(6) 0.5556(5) 0.7577(5) 0.0477(13) Uani 0.59 1 d PDU A 1
H9 H 0.3461 0.5893 0.7369 0.057 Uiso 0.59 1 calc PR A 1
C10 C 0.4630(6) 0.4746(5) 0.8143(4) 0.0511(12) Uani 0.59 1 d PDU A 1
H10 H 0.4123 0.4501 0.8312 0.061 Uiso 0.59 1 calc PR A 1
C11 C 0.5759(5) 0.4281(5) 0.8471(4) 0.0534(13) Uani 0.59 1 d PDU A 1
H11 H 0.6049 0.3742 0.889 0.064 Uiso 0.59 1 calc PR A 1
C12 C 0.6486(6) 0.4588(6) 0.8197(5) 0.0456(14) Uani 0.59 1 d PDU A 1
H12 H 0.7263 0.4259 0.8418 0.055 Uiso 0.59 1 calc PR A 1
C8' C 0.5026(13) 0.6085(12) 0.7245(13) 0.0422(17) Uani 0.41 1 d PDU A 2
H8' H 0.4919 0.6671 0.6903 0.051 Uiso 0.41 1 calc PR A 2
C9' C 0.4180(9) 0.5863(8) 0.7437(7) 0.0484(17) Uani 0.41 1 d PDU A 2
H9' H 0.3497 0.632 0.7244 0.058 Uiso 0.41 1 calc PR A 2
C10' C 0.4327(8) 0.4997(8) 0.7899(6) 0.0521(16) Uani 0.41 1 d PDU A 2
H10' H 0.3734 0.4852 0.8016 0.063 Uiso 0.41 1 calc PR A 2
C11' C 0.5313(8) 0.4322(8) 0.8202(6) 0.0524(15) Uani 0.41 1 d PDU A 2
H11' H 0.5406 0.3719 0.8524 0.063 Uiso 0.41 1 calc PR A 2
C12' C 0.6170(10) 0.4550(10) 0.8022(8) 0.0471(17) Uani 0.41 1 d PDU A 2
H12' H 0.6851 0.4092 0.8215 0.056 Uiso 0.41 1 calc PR A 2
C25 C 0.98632(17) 0.46925(13) 0.84782(11) 0.0237(4) Uani 1 1 d . . .
C26 C 0.90612(19) 0.38772(15) 0.79782(13) 0.0328(4) Uani 1 1 d . . .
H26 H 0.8548 0.3921 0.7361 0.039 Uiso 1 1 calc R . .
C27 C 0.9013(2) 0.30042(16) 0.83818(15) 0.0427(5) Uani 1 1 d . . .
H27 H 0.8469 0.2445 0.8042 0.051 Uiso 1 1 calc R . .
C28 C 0.9759(2) 0.29446(16) 0.92809(16) 0.0455(6) Uani 1 1 d . . .
H28 H 0.9715 0.2347 0.9556 0.055 Uiso 1 1 calc R . .
C29 C 1.0558(2) 0.37383(18) 0.97781(14) 0.0442(6) Uani 1 1 d . . .
H29 H 1.1073 0.3686 1.0395 0.053 Uiso 1 1 calc R . .
C30 C 1.06191(19) 0.46205(16) 0.93818(12) 0.0336(4) Uani 1 1 d . . .
H30 H 1.1174 0.5172 0.9726 0.04 Uiso 1 1 calc R . .
C19 C 1.11615(16) 0.66354(14) 0.86840(11) 0.0244(4) Uani 1 1 d . . .
C20 C 1.10147(18) 0.73850(15) 0.91423(12) 0.0312(4) Uani 1 1 d . . .
H20 H 1.0241 0.7441 0.9069 0.037 Uiso 1 1 calc R . .
C21 C 1.1990(2) 0.80528(16) 0.97059(13) 0.0401(5) Uani 1 1 d . . .
H21 H 1.1887 0.8558 1.0024 0.048 Uiso 1 1 calc R . .
C22 C 1.3102(2) 0.79870(19) 0.98054(15) 0.0474(6) Uani 1 1 d . . .
H22 H 1.3774 0.8439 1.02 0.057 Uiso 1 1 calc R . .
C23 C 1.3248(2) 0.7270(2) 0.93362(17) 0.0588(7) Uani 1 1 d . . .
H23 H 1.4011 0.7242 0.9391 0.071 Uiso 1 1 calc R . .
C24 C 1.2287(2) 0.65888(19) 0.87840(15) 0.0461(6) Uani 1 1 d . . .
H24 H 1.24 0.6084 0.847 0.055 Uiso 1 1 calc R . .
C1 C 1.00531(16) 0.53716(13) 0.71372(10) 0.0214(3) Uani 1 1 d . . .
C2 C 0.94872(16) 0.57655(13) 0.63243(11) 0.0222(4) Uani 1 1 d . . .
H2 H 0.887 0.6296 0.6105 0.027 Uiso 1 1 calc R . .
C3 C 1.07153(16) 0.46434(13) 0.62756(10) 0.0227(4) Uani 1 1 d . . .
H102 H 1.1755(18) 0.3581(13) 0.6261(13) 0.045(6) Uiso 1 1 d D . .
H202 H 1.099(2) 0.4279(18) 0.5424(8) 0.047(7) 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
H H 0 0 '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
C1 S1 C3 88.98(8)
O3 P1 N3 121.29(8)
O3 P1 O1 107.41(7)
N3 P1 O1 105.23(7)
O3 P1 O2 110.36(7)
N3 P1 O2 106.13(8)
O1 P1 O2 105.25(8)
N3 P2 C1 108.13(8)
N3 P2 C25 116.10(8)
C1 P2 C25 105.77(8)
N3 P2 C19 109.86(8)
C1 P2 C19 108.29(8)
C25 P2 C19 108.39(8)
C13 O1 P1 123.09(11)
P1 N3 P2 142.51(10)
C3 N1 C2 110.69(14)
C3 N2 H102 121.4(15)
C3 N2 H202 116.4(15)
H102 N2 H202 121(2)
C14 C13 C18 121.24(18)
C14 C13 O1 121.66(17)
C18 C13 O1 116.99(18)
C13 C14 C15 118.8(2)
C13 C14 H14 120.6
C15 C14 H14 120.6
C16 C15 C14 120.8(2)
C16 C15 H15 119.6
C14 C15 H15 119.6
C17 C16 C15 119.7(2)
C17 C16 H16 120.1
C15 C16 H16 120.1
C16 C17 C18 120.5(2)
C16 C17 H17 119.8
C18 C17 H17 119.8
C13 C18 C17 119.0(2)
C13 C18 H18 120.5
C17 C18 H18 120.5
C7 O2 P1 123.91(12)
C12' C7 C8 110.3(6)
C12' C7 C8' 122.6(8)
C12' C7 O2 121.5(6)
C8 C7 O2 126.9(4)
C8' C7 O2 115.3(6)
C8 C7 C12 119.9(6)
C8' C7 C12 131.4(7)
O2 C7 C12 113.2(4)
C7 C8 C9 120.6(6)
C7 C8 H8 119.7
C9 C8 H8 119.7
C10 C9 C8 119.8(6)
C10 C9 H9 120.1
C8 C9 H9 120.1
C9 C10 C11 120.4(5)
C9 C10 H10 119.8
C11 C10 H10 119.8
C10 C11 C12 120.8(5)
C10 C11 H11 119.6
C12 C11 H11 119.6
C11 C12 C7 118.3(6)
C11 C12 H12 120.8
C7 C12 H12 120.8
C7 C8' C9' 117.0(9)
C7 C8' H8' 121.5
C9' C8' H8' 121.5
C10' C9' C8' 120.3(9)
C10' C9' H9' 119.8
C8' C9' H9' 119.8
C9' C10' C11' 121.8(8)
C9' C10' H10' 119.1
C11' C10' H10' 119.1
C10' C11' C12' 118.1(8)
C10' C11' H11' 121
C12' C11' H11' 121
C7 C12' C11' 120.2(9)
C7 C12' H12' 119.9
C11' C12' H12' 119.9
C30 C25 C26 119.81(17)
C30 C25 P2 122.41(15)
C26 C25 P2 117.75(13)
C27 C26 C25 119.85(19)
C27 C26 H26 120.1
C25 C26 H26 120.1
C26 C27 C28 119.9(2)
C26 C27 H27 120
C28 C27 H27 120
C29 C28 C27 120.65(19)
C29 C28 H28 119.7
C27 C28 H28 119.7
C28 C29 C30 120.11(19)
C28 C29 H29 119.9
C30 C29 H29 119.9
C29 C30 C25 119.7(2)
C29 C30 H30 120.2
C25 C30 H30 120.2
C24 C19 C20 118.69(17)
C24 C19 P2 122.40(14)
C20 C19 P2 118.71(14)
C21 C20 C19 120.38(18)
C21 C20 H20 119.8
C19 C20 H20 119.8
C22 C21 C20 120.14(19)
C22 C21 H21 119.9
C20 C21 H21 119.9
C21 C22 C23 120.1(2)
C21 C22 H22 119.9
C23 C22 H22 119.9
C22 C23 C24 120.1(2)
C22 C23 H23 120
C24 C23 H23 120
C23 C24 C19 120.5(2)
C23 C24 H24 119.7
C19 C24 H24 119.7
C2 C1 S1 109.31(12)
C2 C1 P2 125.28(13)
S1 C1 P2 125.26(10)
C1 C2 N1 117.09(15)
C1 C2 H2 121.5
N1 C2 H2 121.5
N1 C3 N2 124.53(15)
N1 C3 S1 113.91(12)
N2 C3 S1 121.56(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.7439(17)
S1 C3 1.7540(16)
P1 O3 1.4683(13)
P1 N3 1.5613(15)
P1 O1 1.6000(12)
P1 O2 1.6005(13)
P2 N3 1.5624(15)
P2 C1 1.7626(17)
P2 C25 1.8001(17)
P2 C19 1.8028(18)
O1 C13 1.404(2)
N1 C3 1.324(2)
N1 C2 1.365(2)
N2 C3 1.327(2)
N2 H102 0.894(10)
N2 H202 0.905(10)
C13 C14 1.371(3)
C13 C18 1.380(3)
C14 C15 1.392(3)
C14 H14 0.95
C15 C16 1.373(4)
C15 H15 0.95
C16 C17 1.371(4)
C16 H16 0.95
C17 C18 1.390(3)
C17 H17 0.95
C18 H18 0.95
O2 C7 1.401(2)
C7 C12' 1.335(10)
C7 C8 1.344(7)
C7 C8' 1.393(10)
C7 C12 1.422(7)
C8 C9 1.409(8)
C8 H8 0.95
C9 C10 1.359(6)
C9 H9 0.95
C10 C11 1.369(7)
C10 H10 0.95
C11 C12 1.392(7)
C11 H11 0.95
C12 H12 0.95
C8' C9' 1.395(10)
C8' H8' 0.95
C9' C10' 1.359(9)
C9' H9' 0.95
C10' C11' 1.376(10)
C10' H10' 0.95
C11' C12' 1.393(10)
C11' H11' 0.95
C12' H12' 0.95
C25 C30 1.391(2)
C25 C26 1.392(3)
C26 C27 1.381(3)
C26 H26 0.95
C27 C28 1.383(3)
C27 H27 0.95
C28 C29 1.369(3)
C28 H28 0.95
C29 C30 1.389(3)
C29 H29 0.95
C30 H30 0.95
C19 C24 1.385(3)
C19 C20 1.387(3)
C20 C21 1.385(3)
C20 H20 0.95
C21 C22 1.369(3)
C21 H21 0.95
C22 C23 1.372(3)
C22 H22 0.95
C23 C24 1.381(3)
C23 H23 0.95
C24 H24 0.95
C1 C2 1.357(2)
C2 H2 0.95
