#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:16:05 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179053 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/15/4301566.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_4301566
loop_
_publ_author_name
'Ramaswamy Murugavel'
'Ganesan Prabusankar'
'Ashish Sharma'
'Raghavan B. Sunoj'
'Ray J. Butcher'
_publ_contact_author_address
;
Department of Chemistry
Indian Institute of Technology Bombay
Powai
Mumbai
Maharastra
400076
INDIA
;
_publ_contact_author_email       RMV@CHEM.IITB.AC.IN
_publ_contact_author_name        'Ramaswamy Murugavel'
_publ_section_title
;
Conformational and Isomeric Preferences of Six-Membered Inorganic
Heterocycles [EtNP(E)(OR)]3 (E = Lone Pair, O, S, or Se): A Synthetic,
Spectroscopic, Structural, and Computational Study
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2048
_journal_page_last               2059
_journal_paper_doi               10.1021/ic801945q
_journal_volume                  48
_journal_year                    2009
_chemical_formula_sum            'C30 H42 N3 O3 P3 S3'
_chemical_formula_weight         681.76
_chemical_name_systematic
;
 ?
;
_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                 101.10(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.547(2)
_cell_length_b                   15.144(3)
_cell_length_c                   19.175(4)
_cell_measurement_temperature    293(2)
_cell_volume                     3290.4(12)
_computing_cell_refinement       DIF4
_computing_data_collection       DIF4
_computing_data_reduction        REDU4
_computing_molecular_graphics    Pluton/Ortep3
_computing_publication_material  ciftab
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.931
_diffrn_measured_fraction_theta_max 0.931
_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  0.0680
_diffrn_reflns_av_sigmaI/netI    0.0566
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25003
_diffrn_reflns_theta_full        27.34
_diffrn_reflns_theta_max         27.34
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.408
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colouless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.335
_refine_diff_density_min         -1.621
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         6925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1021P)²+0.5252P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1522
_refine_ls_wR_factor_ref         0.1646
_reflns_number_gt                5068
_reflns_number_total             6925
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic801945q_si_001_5.cif
_cod_data_source_block           mur53
_cod_original_cell_volume        3290.3(11)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4301566
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
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.17395(8) 0.34127(5) 0.02722(5) 0.01864(19) Uani 1 1 d . . .
P2 P 0.21237(8) 0.15494(5) 0.02042(5) 0.01804(19) Uani 1 1 d . . .
P3 P 0.14424(8) 0.26048(5) -0.11335(5) 0.01755(19) Uani 1 1 d . . .
S1 S 0.03477(8) 0.33284(6) 0.06700(5) 0.0275(2) Uani 1 1 d . . .
S2 S 0.13160(8) 0.09960(6) 0.08749(5) 0.0260(2) Uani 1 1 d . . .
S3 S 0.03076(11) 0.26739(8) -0.19912(7) 0.0428(3) Uani 1 1 d . . .
N1 N 0.2711(3) 0.25652(17) 0.03851(15) 0.0182(6) Uani 1 1 d . . .
N2 N 0.1271(2) 0.17399(17) -0.05941(15) 0.0182(6) Uani 1 1 d . . .
N3 N 0.1476(3) 0.35279(17) -0.06175(16) 0.0200(6) Uani 1 1 d . . .
O1 O 0.2589(2) 0.42179(15) 0.05454(13) 0.0228(5) Uani 1 1 d . . .
O2 O 0.3263(2) 0.10113(14) 0.00821(13) 0.0212(5) Uani 1 1 d . . .
O3 O 0.2799(2) 0.24682(15) -0.12132(13) 0.0206(5) Uani 1 1 d . . .
C1 C 0.3991(3) 0.2773(2) 0.0363(2) 0.0239(7) Uani 1 1 d . . .
H1A H 0.4376(11) 0.2216(16) 0.0196(5) 0.029 Uiso 1 1 calc R . .
H1B H 0.4010(3) 0.3260(14) -0.0011(11) 0.029 Uiso 1 1 calc R . .
C2 C 0.4730(3) 0.3074(3) 0.1062(2) 0.0310(8) Uani 1 1 d . . .
H2A H 0.4428 0.3624 0.1201 0.046 Uiso 1 1 calc R . .
H2B H 0.5534 0.3150 0.1009 0.046 Uiso 1 1 calc R . .
H2C H 0.4695 0.2637 0.1421 0.046 Uiso 1 1 calc R . .
C3 C 0.0229(3) 0.1142(2) -0.0841(2) 0.0242(7) Uani 1 1 d . . .
H3A H 0.0377(5) 0.0547(18) -0.0581(8) 0.029 Uiso 1 1 calc R . .
H3B H 0.0154(4) 0.1025(4) -0.1376(16) 0.029 Uiso 1 1 calc R . .
C4 C -0.0922(3) 0.1528(3) -0.0708(3) 0.0370(10) Uani 1 1 d . . .
H4A H -0.0864 0.1628 -0.0208 0.056 Uiso 1 1 calc R . .
H4B H -0.1555 0.1122 -0.0873 0.056 Uiso 1 1 calc R . .
H4C H -0.1077 0.2077 -0.0958 0.056 Uiso 1 1 calc R . .
C5 C 0.0652(3) 0.4265(2) -0.0910(2) 0.0235(7) Uani 1 1 d . . .
H5A H 0.0544(5) 0.4644(12) -0.0528(12) 0.028 Uiso 1 1 calc R . .
H5B H -0.010(2) 0.4020(8) -0.1116(7) 0.028 Uiso 1 1 calc R . .
C6 C 0.1099(4) 0.4809(3) -0.1466(2) 0.0322(9) Uani 1 1 d . . .
H6A H 0.1829 0.5088 -0.1255 0.048 Uiso 1 1 calc R . .
H6B H 0.0527 0.5252 -0.1650 0.048 Uiso 1 1 calc R . .
H6C H 0.1227 0.4431 -0.1846 0.048 Uiso 1 1 calc R . .
C11 C 0.2552(3) 0.4814(2) 0.1115(2) 0.0224(7) Uani 1 1 d . . .
C12 C 0.2539(3) 0.4532(2) 0.1807(2) 0.0268(8) Uani 1 1 d . . .
C13 C 0.2555(4) 0.5196(3) 0.2314(2) 0.0319(9) Uani 1 1 d . . .
H13 H 0.2526(4) 0.5019(9) 0.283(2) 0.038 Uiso 1 1 calc R . .
C14 C 0.2609(3) 0.6078(3) 0.2146(2) 0.0321(9) Uani 1 1 d . . .
H14 H 0.2607(3) 0.649(2) 0.2482(19) 0.038 Uiso 1 1 calc R . .
C15 C 0.2664(3) 0.6330(2) 0.1464(2) 0.0302(9) Uani 1 1 d . . .
H15 H 0.2718(5) 0.686(3) 0.1370(6) 0.036 Uiso 1 1 calc R . .
C16 C 0.2631(3) 0.5702(2) 0.0926(2) 0.0242(7) Uani 1 1 d . . .
C17 C 0.2553(4) 0.3585(3) 0.2058(2) 0.0359(9) Uani 1 1 d . . .
H17A H 0.1808 0.3446 0.2183 0.054 Uiso 1 1 calc R . .
H17B H 0.3173 0.3510 0.2466 0.054 Uiso 1 1 calc R . .
H17C H 0.2686 0.3199 0.1684 0.054 Uiso 1 1 calc R . .
C18 C 0.2702(4) 0.5965(2) 0.0177(2) 0.0316(8) Uani 1 1 d . . .
H18A H 0.3323 0.5640 0.0026 0.047 Uiso 1 1 calc R . .
H18B H 0.2862 0.6586 0.0162 0.047 Uiso 1 1 calc R . .
H18C H 0.1965 0.5836 -0.0133 0.047 Uiso 1 1 calc R . .
C21 C 0.3555(3) 0.0144(2) 0.0333(2) 0.0219(7) Uani 1 1 d . . .
C22 C 0.4184(3) 0.0027(3) 0.1017(2) 0.0285(8) Uani 1 1 d . . .
C23 C 0.4490(4) -0.0837(3) 0.1226(3) 0.0357(10) Uani 1 1 d . . .
H23 H 0.481(3) -0.0921(7) 0.159(3) 0.043 Uiso 1 1 calc R . .
C24 C 0.4210(4) -0.1543(3) 0.0766(3) 0.0369(10) Uani 1 1 d . . .
H24 H 0.4403(13) -0.205(3) 0.0900(9) 0.044 Uiso 1 1 calc R . .
C25 C 0.3614(4) -0.1395(2) 0.0092(3) 0.0336(9) Uani 1 1 d . . .
H25 H 0.3448(11) -0.184(3) -0.0198(18) 0.040 Uiso 1 1 calc R . .
C26 C 0.3263(3) -0.0546(2) -0.0147(2) 0.0244(7) Uani 1 1 d . . .
C27 C 0.4548(4) 0.0790(3) 0.1509(2) 0.0371(9) Uani 1 1 d . . .
H27A H 0.5149 0.1125 0.1345 0.056 Uiso 1 1 calc R . .
H27B H 0.4851 0.0573 0.1979 0.056 Uiso 1 1 calc R . .
H27C H 0.3877 0.1161 0.1518 0.056 Uiso 1 1 calc R . .
C28 C 0.2615(4) -0.0397(3) -0.0895(3) 0.0406(10) Uani 1 1 d . . .
H28A H 0.1788 -0.0324 -0.0897 0.061 Uiso 1 1 calc R . .
H28B H 0.2728 -0.0896 -0.1183 0.061 Uiso 1 1 calc R . .
H28C H 0.2914 0.0125 -0.1083 0.061 Uiso 1 1 calc R . .
C31 C 0.3199(3) 0.2660(2) -0.18530(19) 0.0216(7) Uani 1 1 d . . .
C32 C 0.3855(3) 0.3432(2) -0.1879(2) 0.0261(8) Uani 1 1 d . . .
C33 C 0.4310(4) 0.3573(3) -0.2497(2) 0.0330(9) Uani 1 1 d . . .
H33 H 0.473(2) 0.406(3) -0.2532(3) 0.040 Uiso 1 1 calc R . .
C34 C 0.4127(4) 0.2985(3) -0.3047(3) 0.0414(11) Uani 1 1 d . . .
H34 H 0.4494(18) 0.3110(7) -0.352(2) 0.050 Uiso 1 1 calc R . .
C35 C 0.3476(4) 0.2233(3) -0.3003(2) 0.0382(10) Uani 1 1 d . . .
H35 H 0.3370(8) 0.188(2) -0.334(2) 0.046 Uiso 1 1 calc R . .
C36 C 0.2986(4) 0.2045(2) -0.2402(2) 0.0287(8) Uani 1 1 d . . .
C37 C 0.4126(4) 0.4068(3) -0.1272(2) 0.0341(9) Uani 1 1 d . . .
H37A H 0.3449 0.4128 -0.1054 0.051 Uiso 1 1 calc R . .
H37B H 0.4322 0.4633 -0.1445 0.051 Uiso 1 1 calc R . .
H37C H 0.4782 0.3852 -0.0928 0.051 Uiso 1 1 calc R . .
C38 C 0.2306(5) 0.1200(3) -0.2367(2) 0.0394(10) Uani 1 1 d . . .
H38A H 0.2268 0.1073 -0.1882 0.059 Uiso 1 1 calc R . .
H38B H 0.2696 0.0724 -0.2559 0.059 Uiso 1 1 calc R . .
H38C H 0.1520 0.1266 -0.2639 0.059 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'
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'
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
O1 P1 N3 103.55(14) . . ?
O1 P1 N1 100.82(14) . . ?
N3 P1 N1 101.21(14) . . ?
O1 P1 S1 115.65(10) . . ?
N3 P1 S1 114.18(12) . . ?
N1 P1 S1 119.11(10) . . ?
O2 P2 N2 107.95(14) . . ?
O2 P2 N1 100.62(13) . . ?
N2 P2 N1 99.94(14) . . ?
O2 P2 S2 113.22(10) . . ?
N2 P2 S2 114.24(10) . . ?
N1 P2 S2 119.17(11) . . ?
O3 P3 N2 100.80(13) . . ?
O3 P3 N3 104.19(14) . . ?
N2 P3 N3 105.65(14) . . ?
O3 P3 S3 116.42(11) . . ?
N2 P3 S3 115.26(11) . . ?
N3 P3 S3 113.04(11) . . ?
C1 N1 P2 122.5(2) . . ?
C1 N1 P1 117.6(2) . . ?
P2 N1 P1 115.73(17) . . ?
C3 N2 P2 118.4(2) . . ?
C3 N2 P3 116.8(2) . . ?
P2 N2 P3 124.71(17) . . ?
C5 N3 P1 115.6(2) . . ?
C5 N3 P3 116.7(2) . . ?
P1 N3 P3 118.78(16) . . ?
C11 O1 P1 129.1(2) . . ?
C21 O2 P2 124.7(2) . . ?
C31 O3 P3 122.5(2) . . ?
C2 C1 N1 114.9(3) . . ?
N2 C3 C4 112.8(3) . . ?
N3 C5 C6 112.9(3) . . ?
C12 C11 C16 123.6(3) . . ?
C12 C11 O1 122.8(3) . . ?
C16 C11 O1 113.4(3) . . ?
C11 C12 C13 116.1(3) . . ?
C11 C12 C17 126.3(3) . . ?
C13 C12 C17 117.6(3) . . ?
C14 C13 C12 122.0(4) . . ?
C15 C14 C13 120.2(3) . . ?
C14 C15 C16 120.9(4) . . ?
C15 C16 C11 117.1(4) . . ?
C15 C16 C18 121.6(3) . . ?
C11 C16 C18 121.2(3) . . ?
C22 C21 C26 123.2(3) . . ?
C22 C21 O2 119.1(3) . . ?
C26 C21 O2 117.5(3) . . ?
C21 C22 C23 116.7(4) . . ?
C21 C22 C27 122.0(3) . . ?
C23 C22 C27 121.2(4) . . ?
C24 C23 C22 121.9(4) . . ?
C25 C24 C23 119.4(4) . . ?
C24 C25 C26 121.6(4) . . ?
C21 C26 C25 117.2(4) . . ?
C21 C26 C28 122.1(3) . . ?
C25 C26 C28 120.7(4) . . ?
C36 C31 C32 123.4(3) . . ?
C36 C31 O3 118.5(3) . . ?
C32 C31 O3 118.0(3) . . ?
C31 C32 C33 116.8(4) . . ?
C31 C32 C37 123.0(3) . . ?
C33 C32 C37 120.1(3) . . ?
C34 C33 C32 121.7(4) . . ?
C33 C34 C35 119.8(4) . . ?
C34 C35 C36 121.8(4) . . ?
C31 C36 C35 116.4(4) . . ?
C31 C36 C38 123.5(3) . . ?
C35 C36 C38 120.1(4) . . ?
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
P1 O1 1.589(3) . ?
P1 N3 1.683(3) . ?
P1 N1 1.691(3) . ?
P1 S1 1.9113(13) . ?
P2 O2 1.603(2) . ?
P2 N2 1.678(3) . ?
P2 N1 1.690(3) . ?
P2 S2 1.9204(12) . ?
P3 O3 1.617(2) . ?
P3 N2 1.704(3) . ?
P3 N3 1.709(3) . ?
P3 S3 1.8981(17) . ?
N1 C1 1.520(4) . ?
N2 C3 1.507(4) . ?
N3 C5 1.503(4) . ?
O1 C11 1.424(4) . ?
O2 C21 1.417(4) . ?
O3 C31 1.421(4) . ?
C1 C2 1.514(5) . ?
C3 C4 1.518(5) . ?
C5 C6 1.515(5) . ?
C11 C12 1.396(5) . ?
C11 C16 1.401(5) . ?
C12 C13 1.397(5) . ?
C12 C17 1.511(5) . ?
C13 C14 1.379(6) . ?
C14 C15 1.376(6) . ?
C15 C16 1.397(5) . ?
C16 C18 1.507(6) . ?
C21 C22 1.384(6) . ?
C21 C26 1.390(5) . ?
C22 C23 1.394(5) . ?
C22 C27 1.499(6) . ?
C23 C24 1.384(7) . ?
C24 C25 1.361(7) . ?
C25 C26 1.397(5) . ?
C26 C28 1.502(6) . ?
C31 C36 1.391(5) . ?
C31 C32 1.399(5) . ?
C32 C33 1.402(5) . ?
C32 C37 1.497(6) . ?
C33 C34 1.366(7) . ?
C34 C35 1.376(6) . ?
C35 C36 1.408(5) . ?
C36 C38 1.510(6) . ?
