#------------------------------------------------------------------------------
#$Date: 2016-03-25 16:37:18 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179980 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/74/7027454.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7027454
loop_
_publ_author_name
'Alder, Mark J.'
'Cross, Wendy I.'
'Flower, Kevin R.'
'Pritchard, Robin G.'
_publ_section_title
;
 Azo-containing tertiary phosphines: synthesis, reactivity and structural
 characterisation
;
_journal_issue                   15
_journal_name_full
'Journal of the Chemical Society, Dalton Transactions'
_journal_page_first              2563
_journal_paper_doi               10.1039/a902885d
_journal_year                    1999
_chemical_formula_sum            'C31 H25 N2 O2 P S'
_chemical_formula_weight         520.56
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.558(17)
_cell_angle_beta                 94.483(18)
_cell_angle_gamma                108.463(16)
_cell_formula_units_Z            2
_cell_length_a                   8.865(2)
_cell_length_b                   12.054(3)
_cell_length_c                   13.935(3)
_cell_measurement_temperature    203(2)
_cell_volume                     1321.6(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4969
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.215
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     412
_refine_ls_number_reflns         4640
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0543P)²+0.4784P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1077
_reflns_number_gt                3501
_reflns_number_total             4640
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            902885dsup1.cif
_cod_data_source_block           mald6
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1321.5(5)
_cod_database_code               7027454
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -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
S1 S 0.25124(8) 0.68422(6) 0.03971(5) 0.03844(18) Uani 1 1 d .
N1 N 0.7071(2) 0.6003(2) 0.51672(16) 0.0383(5) Uani 1 1 d .
N2 N 0.7437(2) 0.53841(19) 0.56383(17) 0.0398(5) Uani 1 1 d .
P1 P 0.36650(7) 0.79525(5) 0.17744(4) 0.02805(16) Uani 1 1 d .
O1 O 0.83410(19) 0.41169(15) 0.39707(13) 0.0353(4) Uani 1 1 d .
O2 O 0.6093(2) 0.25312(16) 0.38608(13) 0.0413(4) Uani 1 1 d .
H3 H 0.776(3) 0.375(2) 0.2104(19) 0.035(7) Uiso 1 1 d .
H4 H 0.631(3) 0.457(2) 0.1232(19) 0.029(6) Uiso 1 1 d .
H5 H 0.492(3) 0.601(2) 0.1253(19) 0.030(6) Uiso 1 1 d .
H7 H 0.438(3) 0.820(2) 0.3923(19) 0.039(7) Uiso 1 1 d .
H8 H 0.554(3) 0.725(2) 0.476(2) 0.042(7) Uiso 1 1 d .
H12 H 0.678(4) 0.727(3) 0.692(2) 0.061(10) Uiso 1 1 d .
H13 H 0.709(4) 0.805(3) 0.865(2) 0.060(9) Uiso 1 1 d .
H15 H 0.914(3) 0.552(2) 0.876(2) 0.045(7) Uiso 1 1 d .
H16 H 0.871(3) 0.475(3) 0.693(2) 0.056(8) Uiso 1 1 d .
H19 H 0.379(3) 1.030(2) 0.3210(18) 0.036(7) Uiso 1 1 d .
H20 H 0.199(4) 1.094(3) 0.410(2) 0.064(10) Uiso 1 1 d .
H21 H -0.049(4) 0.955(3) 0.407(2) 0.058(9) Uiso 1 1 d .
H22 H -0.120(4) 0.756(3) 0.305(2) 0.059(9) Uiso 1 1 d .
H23 H 0.053(3) 0.685(3) 0.205(2) 0.050(8) Uiso 1 1 d .
H25 H 0.379(4) 0.994(3) 0.105(2) 0.056(8) Uiso 1 1 d .
H26 H 0.600(4) 1.158(3) 0.089(2) 0.063(9) Uiso 1 1 d .
H27 H 0.864(4) 1.185(3) 0.146(2) 0.063(9) Uiso 1 1 d .
H28 H 0.921(4) 1.055(3) 0.222(2) 0.068(10) Uiso 1 1 d .
H29 H 0.710(3) 0.897(3) 0.244(2) 0.047(8) Uiso 1 1 d .
C1 C 0.6844(3) 0.5498(2) 0.40777(17) 0.0290(5) Uani 1 1 d .
C2 C 0.7428(3) 0.4630(2) 0.35070(18) 0.0311(5) Uani 1 1 d .
C3 C 0.7264(3) 0.4306(2) 0.24449(19) 0.0352(6) Uani 1 1 d .
C4 C 0.6464(3) 0.4815(2) 0.19371(19) 0.0337(5) Uani 1 1 d .
C5 C 0.5066(3) 0.6284(2) 0.19603(18) 0.0290(5) Uani 1 1 d .
C6 C 0.4555(3) 0.7207(2) 0.24827(17) 0.0275(5) Uani 1 1 d .
C7 C 0.4775(3) 0.7573(2) 0.35589(18) 0.0306(5) Uani 1 1 d .
C8 C 0.5474(3) 0.7013(2) 0.40771(19) 0.0305(5) Uani 1 1 d .
C9 C 0.6052(3) 0.6077(2) 0.35565(17) 0.0272(5) Uani 1 1 d .
C10 C 0.5842(3) 0.5711(2) 0.24730(17) 0.0276(5) Uani 1 1 d .
C11 C 0.7681(3) 0.5967(2) 0.67369(18) 0.0360(6) Uani 1 1 d .
C12 C 0.7177(3) 0.6931(3) 0.7207(2) 0.0444(7) Uani 1 1 d .
C13 C 0.7394(3) 0.7385(3) 0.8279(2) 0.0469(7) Uani 1 1 d .
C14 C 0.8100(3) 0.6858(3) 0.88625(18) 0.0398(6) Uani 1 1 d .
C15 C 0.8596(3) 0.5904(2) 0.8360(2) 0.0388(6) Uani 1 1 d .
C16 C 0.8382(3) 0.5454(3) 0.7311(2) 0.0387(6) Uani 1 1 d .
C17 C 0.8286(4) 0.7305(4) 1.0014(2) 0.0720(10) Uani 1 1 d .
H17A H 0.8402 0.6663 1.0266 0.108 Uiso 1 1 calc R
H17B H 0.7335 0.7482 1.0203 0.108 Uiso 1 1 calc R
H17C H 0.9240 0.8056 1.0313 0.108 Uiso 1 1 calc R
C18 C 0.2353(3) 0.8531(2) 0.25566(17) 0.0285(5) Uani 1 1 d .
C19 C 0.2803(3) 0.9756(3) 0.3194(2) 0.0412(6) Uani 1 1 d .
C20 C 0.1738(4) 1.0138(3) 0.3759(2) 0.0504(7) Uani 1 1 d .
C21 C 0.0237(3) 0.9306(3) 0.3697(2) 0.0469(7) Uani 1 1 d .
C22 C -0.0207(3) 0.8086(3) 0.3078(2) 0.0447(7) Uani 1 1 d .
C23 C 0.0834(3) 0.7696(2) 0.2496(2) 0.0369(6) Uani 1 1 d .
C24 C 0.5311(3) 0.9292(2) 0.17750(18) 0.0313(5) Uani 1 1 d .
C25 C 0.4973(3) 1.0090(2) 0.1324(2) 0.0406(6) Uani 1 1 d .
C26 C 0.6208(4) 1.1052(3) 0.1228(2) 0.0469(7) Uani 1 1 d .
C27 C 0.7789(4) 1.1229(3) 0.1572(2) 0.0503(8) Uani 1 1 d .
C28 C 0.8136(4) 1.0463(3) 0.2029(3) 0.0543(8) Uani 1 1 d .
C29 C 0.6903(3) 0.9496(3) 0.2137(2) 0.0440(7) Uani 1 1 d .
C30 C 0.7520(3) 0.3055(2) 0.41415(19) 0.0352(6) Uani 1 1 d .
C31 C 0.8647(3) 0.2676(3) 0.4706(2) 0.0505(7) Uani 1 1 d .
H31A H 0.8033 0.1953 0.4866 0.076 Uiso 1 1 calc R
H31B H 0.9236 0.3357 0.5337 0.076 Uiso 1 1 calc R
H31C H 0.9406 0.2471 0.4283 0.076 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'
O O 0.0106 0.0060 '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'
N N 0.0061 0.0033 '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
N2 N1 C1 116.0(2)
N1 N2 C11 112.8(2)
C24 P1 C6 105.69(11)
C24 P1 C18 106.99(11)
C6 P1 C18 105.29(10)
C24 P1 S1 112.78(8)
C6 P1 S1 113.06(8)
C18 P1 S1 112.45(8)
C30 O1 C2 117.01(18)
C2 C1 N1 127.5(2)
C2 C1 C9 118.4(2)
N1 C1 C9 113.7(2)
C1 C2 O1 121.5(2)
C1 C2 C3 121.9(2)
O1 C2 C3 116.3(2)
C4 C3 C2 120.2(2)
C3 C4 C10 120.8(2)
C6 C5 C10 121.6(2)
C5 C6 C7 119.0(2)
C5 C6 P1 118.89(17)
C7 C6 P1 122.05(18)
C8 C7 C6 121.0(2)
C7 C8 C9 121.1(2)
C8 C9 C10 118.1(2)
C8 C9 C1 122.7(2)
C10 C9 C1 119.2(2)
C4 C10 C5 121.4(2)
C4 C10 C9 119.3(2)
C5 C10 C9 119.2(2)
C16 C11 C12 120.3(2)
C16 C11 N2 115.7(2)
C12 C11 N2 123.9(2)
C11 C12 C13 119.3(3)
C14 C13 C12 120.3(3)
C15 C14 C13 118.3(2)
C15 C14 C17 120.8(3)
C13 C14 C17 120.9(3)
C16 C15 C14 121.7(3)
C11 C16 C15 120.1(3)
C23 C18 C19 119.5(2)
C23 C18 P1 117.51(19)
C19 C18 P1 123.02(18)
C20 C19 C18 120.0(3)
C21 C20 C19 120.2(3)
C20 C21 C22 120.0(3)
C21 C22 C23 120.5(3)
C22 C23 C18 119.8(3)
C29 C24 C25 119.0(2)
C29 C24 P1 122.07(19)
C25 C24 P1 118.72(19)
C26 C25 C24 120.2(3)
C25 C26 C27 120.2(3)
C28 C27 C26 120.2(3)
C27 C28 C29 120.3(3)
C28 C29 C24 120.2(3)
O2 C30 O1 122.7(2)
O2 C30 C31 126.9(2)
O1 C30 C31 110.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 P1 1.9484(10)
N1 N2 1.227(3)
N1 C1 1.426(3)
N2 C11 1.445(3)
P1 C24 1.801(2)
P1 C6 1.807(2)
P1 C18 1.811(2)
O1 C30 1.358(3)
O1 C2 1.390(3)
O2 C30 1.192(3)
C1 C2 1.378(3)
C1 C9 1.429(3)
C2 C3 1.395(3)
C3 C4 1.356(4)
C4 C10 1.408(3)
C5 C6 1.362(3)
C5 C10 1.409(3)
C6 C7 1.408(3)
C7 C8 1.361(3)
C8 C9 1.412(3)
C9 C10 1.418(3)
C11 C16 1.369(4)
C11 C12 1.377(4)
C12 C13 1.401(4)
C13 C14 1.392(4)
C14 C15 1.375(4)
C14 C17 1.508(4)
C15 C16 1.370(4)
C18 C23 1.381(3)
C18 C19 1.381(3)
C19 C20 1.377(4)
C20 C21 1.367(4)
C21 C22 1.370(4)
C22 C23 1.375(4)
C24 C29 1.379(4)
C24 C25 1.388(3)
C25 C26 1.369(4)
C26 C27 1.373(4)
C27 C28 1.362(4)
C28 C29 1.378(4)
C30 C31 1.486(4)
