#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/68/7216894.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_7216894
loop_
_publ_author_name
'Alder, Mark J.'
'Bates, Vanessa M.'
'Cross, Wendy I.'
'Flower, Kevin R.'
'Pritchard, Robin G.'
_publ_section_title
;
 The synthesis and structural characterisation of some azo-containing
 phosphine chalcogenides and comparison to non-phosphorus-containing
 analogues
;
_journal_issue                   20
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2669
_journal_paper_doi               10.1039/b104918f
_journal_year                    2001
_chemical_formula_sum            'C26.78 H24.99 Cl1.1 N2 O P S'
_chemical_formula_weight         492.92
_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                110.513(16)
_cell_angle_beta                 94.713(13)
_cell_angle_gamma                91.063(12)
_cell_formula_units_Z            2
_cell_length_a                   8.8661(12)
_cell_length_b                   10.5570(18)
_cell_length_c                   14.267(3)
_cell_measurement_temperature    203(2)
_cell_volume                     1244.9(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4676
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    0.335
_exptl_absorpt_correction_T_max  0.9361
_exptl_absorpt_correction_T_min  0.8919
_exptl_crystal_colour            'red orange'
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             515
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.150
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         4368
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0610
_refine_ls_shift/su_max          0.112
_refine_ls_shift/su_mean         0.017
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1281P)²+1.1007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1813
_refine_ls_wR_factor_ref         0.1918
_reflns_number_gt                3720
_reflns_number_total             4368
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b104918f.txt
_cod_data_source_block           comp2b
_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
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_formula_sum        'C26.78 H24.99 Cl1.10 N2 O P S'
_cod_database_code               7216894
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 0.30538(9) 0.17017(8) 0.47410(6) 0.0349(3) Uani 1 1 d .
N1 N 0.1763(3) 0.1577(3) 0.92941(19) 0.0324(6) Uani 1 1 d .
N2 N 0.2159(3) 0.0981(3) 0.98955(18) 0.0316(6) Uani 1 1 d .
P1 P 0.25136(8) 0.26478(7) 0.61049(5) 0.0254(2) Uani 1 1 d .
O1 O 0.4367(3) -0.0175(3) 0.8919(2) 0.0456(7) Uani 1 1 d .
C1 C 0.2638(3) 0.1301(3) 0.8469(2) 0.0291(6) Uani 1 1 d .
C2 C 0.3871(4) 0.0441(3) 0.8284(2) 0.0334(7) Uani 1 1 d .
C3 C 0.4596(4) 0.0229(3) 0.7422(2) 0.0352(7) Uani 1 1 d .
C4 C 0.4152(3) 0.0857(3) 0.6755(2) 0.0316(7) Uani 1 1 d .
C5 C 0.2954(3) 0.1735(3) 0.6940(2) 0.0275(6) Uani 1 1 d .
C6 C 0.2212(3) 0.1941(3) 0.7793(2) 0.0292(6) Uani 1 1 d .
C7 C 0.1302(3) 0.1229(3) 1.0728(2) 0.0309(7) Uani 1 1 d .
C8 C 0.0109(4) 0.2084(3) 1.0930(2) 0.0381(7) Uani 1 1 d .
H8 H -0.0192 0.2542 1.0492 0.046 Uiso 1 1 calc R
C9 C -0.0632(4) 0.2262(4) 1.1773(3) 0.0405(8) Uani 1 1 d .
C10 C -0.0200(4) 0.1617(3) 1.2444(2) 0.0341(7) Uani 1 1 d .
C11 C 0.0975(4) 0.0743(3) 1.2222(2) 0.0350(7) Uani 1 1 d .
C12 C 0.1720(4) 0.0542(3) 1.1371(2) 0.0335(7) Uani 1 1 d .
C13 C -0.0970(4) 0.1872(4) 1.3394(3) 0.0433(8) Uani 1 1 d .
H13A H -0.1123 0.1025 1.3504 0.065 Uiso 1 1 calc R
H13B H -0.1943 0.2254 1.3328 0.065 Uiso 1 1 calc R
H13C H -0.0340 0.2501 1.3959 0.065 Uiso 1 1 calc R
C14 C 0.0523(3) 0.2963(3) 0.6153(2) 0.0290(6) Uani 1 1 d .
C15 C -0.0523(4) 0.1875(4) 0.5933(2) 0.0363(7) Uani 1 1 d .
C16 C -0.2047(4) 0.2079(4) 0.5864(3) 0.0464(9) Uani 1 1 d .
C17 C -0.2556(4) 0.3346(5) 0.6000(3) 0.0542(10) Uani 1 1 d .
C18 C -0.1552(4) 0.4424(5) 0.6233(4) 0.0585(11) Uani 1 1 d .
C19 C 0.0000(4) 0.4245(4) 0.6307(3) 0.0439(8) Uani 1 1 d .
C20 C 0.3518(3) 0.4281(3) 0.6680(2) 0.0295(6) Uani 1 1 d .
C21 C 0.3826(4) 0.5033(3) 0.6091(3) 0.0378(7) Uani 1 1 d .
C22 C 0.4655(4) 0.6246(4) 0.6494(3) 0.0478(9) Uani 1 1 d .
C23 C 0.5201(5) 0.6709(4) 0.7474(4) 0.0553(10) Uani 1 1 d .
C24 C 0.4908(6) 0.5990(5) 0.8074(3) 0.0676(13) Uani 1 1 d .
H24 H 0.5283 0.6323 0.8756 0.081 Uiso 1 1 calc R
C25 C 0.4057(5) 0.4769(4) 0.7684(3) 0.0527(10) Uani 1 1 d .
C26 C 0.1852(12) 0.7058(9) 1.1379(6) 0.078(3) Uani 0.551(5) 1 d PD
H26A H 0.2277 0.7538 1.2073 0.094 Uiso 0.551(5) 1 calc PR
H26B H 0.1040 0.7581 1.1211 0.094 Uiso 0.551(5) 1 calc PR
Cl1 Cl 0.3382(3) 0.6799(4) 1.0477(2) 0.0968(12) Uani 0.551(5) 1 d PD
Cl2 Cl 0.1182(5) 0.5463(4) 1.1230(4) 0.1257(16) Uani 0.551(5) 1 d PD
H12 H 0.256(4) -0.008(4) 1.119(3) 0.039(9) Uiso 1 1 d .
H4 H 0.467(5) 0.073(4) 0.618(3) 0.049(11) Uiso 1 1 d .
H6 H 0.140(4) 0.258(3) 0.796(2) 0.029(8) Uiso 1 1 d .
H19 H 0.073(4) 0.505(4) 0.647(3) 0.041(10) Uiso 1 1 d .
H15 H -0.020(4) 0.097(4) 0.584(3) 0.038(9) Uiso 1 1 d .
H11 H 0.131(4) 0.021(4) 1.265(3) 0.041(10) Uiso 1 1 d .
H9 H -0.147(5) 0.284(4) 1.184(3) 0.044(10) Uiso 1 1 d .
H3 H 0.542(4) -0.038(4) 0.730(3) 0.036(9) Uiso 1 1 d .
H17 H -0.356(5) 0.345(4) 0.589(3) 0.043(10) Uiso 1 1 d .
H16 H -0.266(5) 0.143(4) 0.576(3) 0.048(11) Uiso 1 1 d .
H1 H 0.385(6) -0.002(5) 0.935(4) 0.059(14) Uiso 1 1 d .
H25 H 0.389(5) 0.423(5) 0.812(3) 0.062(12) Uiso 1 1 d .
H22 H 0.476(5) 0.677(5) 0.611(4) 0.065(13) Uiso 1 1 d .
C27 C 0.3728(17) 0.556(3) 1.0296(9) 0.135(10) Uani 0.415(11) 1 d PD
H27A H 0.4592 0.5060 1.0396 0.203 Uiso 0.415(11) 1 calc PR
H27B H 0.3747 0.6419 1.0853 0.203 Uiso 0.415(11) 1 calc PR
H27C H 0.3773 0.5736 0.9674 0.203 Uiso 0.415(11) 1 calc PR
C28 C 0.224(2) 0.4725(13) 1.0240(14) 0.146(10) Uani 0.415(11) 1 d PD
H28A H 0.2272 0.3873 0.9673 0.175 Uiso 0.415(11) 1 calc PR
H28B H 0.2296 0.4489 1.0848 0.175 Uiso 0.415(11) 1 calc PR
C29 C 0.068(2) 0.523(2) 1.014(2) 0.160(12) Uani 0.415(11) 1 d PD
H29A H 0.0602 0.5884 1.0815 0.192 Uiso 0.415(11) 1 calc PR
H29B H 0.0827 0.5782 0.9724 0.192 Uiso 0.415(11) 1 calc PR
H21 H 0.352(4) 0.461(4) 0.539(3) 0.047(10) Uiso 1 1 d .
H23 H 0.574(6) 0.757(6) 0.766(4) 0.092(17) Uiso 1 1 d .
H18 H -0.199(5) 0.522(5) 0.633(4) 0.066(13) Uiso 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'
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'
Cl Cl 0.1484 0.1585 '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
N2 N1 C1 114.4(3) .
N1 N2 C7 115.9(3) .
C5 P1 C14 106.22(14) .
C5 P1 C20 105.84(14) .
C14 P1 C20 106.26(14) .
C5 P1 S1 113.04(10) .
C14 P1 S1 113.02(10) .
C20 P1 S1 111.89(10) .
C6 C1 N1 115.3(3) .
C6 C1 C2 119.1(3) .
N1 C1 C2 125.6(3) .
O1 C2 C3 118.7(3) .
O1 C2 C1 122.1(3) .
C3 C2 C1 119.3(3) .
C4 C3 C2 121.0(3) .
C3 C4 C5 120.3(3) .
C6 C5 C4 119.0(3) .
C6 C5 P1 121.9(2) .
C4 C5 P1 118.9(2) .
C5 C6 C1 121.2(3) .
C8 C7 C12 119.6(3) .
C8 C7 N2 124.8(3) .
C12 C7 N2 115.5(3) .
C9 C8 C7 119.7(3) .
C8 C9 C10 121.6(3) .
C11 C10 C9 118.0(3) .
C11 C10 C13 120.8(3) .
C9 C10 C13 121.2(3) .
C12 C11 C10 121.0(3) .
C11 C12 C7 119.9(3) .
C19 C14 C15 119.1(3) .
C19 C14 P1 121.5(2) .
C15 C14 P1 119.2(2) .
C16 C15 C14 119.9(3) .
C15 C16 C17 120.7(4) .
C18 C17 C16 120.2(4) .
C17 C18 C19 120.2(4) .
C14 C19 C18 119.9(4) .
C25 C20 C21 118.8(3) .
C25 C20 P1 121.8(3) .
C21 C20 P1 119.3(3) .
C22 C21 C20 120.8(4) .
C23 C22 C21 120.2(4) .
C22 C23 C24 120.3(4) .
C23 C24 C25 120.5(4) .
C20 C25 C24 119.5(4) .
Cl2 C26 Cl1 105.2(5) .
C29 C28 C27 123.7(13) .
C29 C29 C28 140(3) 2_567
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 P1 1.9550(11) .
N1 N2 1.262(4) .
N1 C1 1.411(4) .
N2 C7 1.413(4) .
P1 C5 1.800(3) .
P1 C14 1.805(3) .
P1 C20 1.808(3) .
O1 C2 1.340(4) .
C1 C6 1.391(4) .
C1 C2 1.416(4) .
C2 C3 1.385(5) .
C3 C4 1.375(4) .
C4 C5 1.403(4) .
C5 C6 1.383(4) .
C7 C8 1.386(5) .
C7 C12 1.387(4) .
C8 C9 1.376(5) .
C9 C10 1.390(5) .
C10 C11 1.387(5) .
C10 C13 1.509(4) .
C11 C12 1.383(5) .
C14 C19 1.388(5) .
C14 C15 1.392(5) .
C15 C16 1.373(5) .
C16 C17 1.372(6) .
C17 C18 1.359(6) .
C18 C19 1.393(5) .
C20 C25 1.381(5) .
C20 C21 1.382(4) .
C21 C22 1.374(5) .
C22 C23 1.353(6) .
C23 C24 1.364(6) .
C24 C25 1.390(6) .
C26 Cl2 1.710(9) .
C26 Cl1 1.904(9) .
C27 C28 1.560(17) .
C28 C29 1.499(17) .
C29 C29 1.27(3) 2_567
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 N2 0.76(5) 1.91(5) 2.570(4) 144(5)
