#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:01:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178456 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/77/4027775.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_4027775
loop_
_publ_author_name
'Qiuli Yao'
'Chengye Yuan'
_publ_section_title
;
 Stereospecific Transformation of Protected P-H Group into P-O or P-N
 Group in One-Pot Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10985
_journal_page_last               10990
_journal_paper_doi               10.1021/jo302140q
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H25 N2 O7 P S'
_chemical_formula_sum            'C15 H25 N2 O7 P S'
_chemical_formula_weight         408.40
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 114.84(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.234(4)
_cell_length_b                   12.276(3)
_cell_length_c                   10.907(2)
_cell_measurement_reflns_used    3561
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.98
_cell_measurement_theta_min      5.07
_cell_volume                     2337.1(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7846
_diffrn_reflns_theta_full        66.98
_diffrn_reflns_theta_max         66.98
_diffrn_reflns_theta_min         5.07
_exptl_absorpt_coefficient_mu    2.172
_exptl_absorpt_correction_T_max  0.7365
_exptl_absorpt_correction_T_min  0.5815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.730
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.129
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3961
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0726
_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)+(0.1482P)²+0.0275P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1906
_refine_ls_wR_factor_ref         0.1983
_reflns_number_gt                3561
_reflns_number_total             3961
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302140q_si_004.cif
_cod_data_source_block           034
_cod_original_cell_volume        2337.2(8)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4027775
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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 0.83241(5) 0.21232(8) 0.13838(7) 0.0977(3) Uani 1 1 d .
P1 P 0.88698(5) 0.20600(9) 0.55527(9) 0.0950(3) Uani 1 1 d .
O1 O 0.8539(2) 0.3225(3) 0.5527(5) 0.1422(15) Uani 1 1 d .
O2 O 0.8512(3) 0.1402(5) 0.6347(4) 0.1364(14) Uani 1 1 d .
O3 O 0.96911(14) 0.2031(3) 0.6034(2) 0.1021(8) Uani 1 1 d .
O4 O 0.8920(2) 0.1777(3) 0.1035(3) 0.1220(11) Uani 1 1 d .
O5 O 0.7622(2) 0.1527(3) 0.0859(3) 0.1272(12) Uani 1 1 d .
O6 O 0.8460(8) -0.3680(5) 0.3875(13) 0.277(5) Uani 1 1 d .
O7 O 0.9410(7) -0.3365(5) 0.3485(10) 0.222(4) Uani 1 1 d .
N1 N 0.86584(15) 0.2158(3) 0.3039(2) 0.0868(7) Uani 1 1 d .
H1A H 0.9043 0.2576 0.3472 0.104 Uiso 1 1 calc R
N2 N 0.8891(7) -0.3036(6) 0.3738(8) 0.179(3) Uani 1 1 d .
C1 C 0.8513(2) 0.0304(3) 0.3832(4) 0.0888(9) Uani 1 1 d .
C2 C 0.8099(4) -0.0464(5) 0.4191(6) 0.1289(18) Uani 1 1 d .
H2A H 0.7728 -0.0221 0.4462 0.155 Uiso 1 1 calc R
C3 C 0.8215(5) -0.1554(6) 0.4162(7) 0.146(2) Uani 1 1 d .
H3B H 0.7914 -0.2054 0.4361 0.176 Uiso 1 1 calc R
C4 C 0.8793(4) -0.1886(4) 0.3828(6) 0.130(2) Uani 1 1 d .
C5 C 0.9222(3) -0.1166(4) 0.3477(6) 0.1146(13) Uani 1 1 d .
H5B H 0.9603 -0.1413 0.3233 0.138 Uiso 1 1 calc R
C6 C 0.9078(2) -0.0077(3) 0.3491(5) 0.0972(10) Uani 1 1 d .
H6A H 0.9371 0.0418 0.3264 0.117 Uiso 1 1 calc R
C7 C 0.83434(19) 0.1520(4) 0.3829(4) 0.0917(9) Uani 1 1 d .
C8 C 0.7474(2) 0.1747(6) 0.3390(6) 0.1285(18) Uani 1 1 d .
H8A H 0.7187 0.1474 0.2493 0.193 Uiso 1 1 calc R
H8B H 0.7393 0.2518 0.3405 0.193 Uiso 1 1 calc R
H8C H 0.7308 0.1390 0.4003 0.193 Uiso 1 1 calc R
C9 C 0.8111(4) 0.3531(4) 0.0859(5) 0.1254(17) Uani 1 1 d .
C10 C 0.7884(7) 0.3507(8) -0.0689(6) 0.192(4) Uani 1 1 d .
H10A H 0.7766 0.4232 -0.1047 0.287 Uiso 1 1 calc R
H10B H 0.7444 0.3049 -0.1124 0.287 Uiso 1 1 calc R
H10C H 0.8304 0.3225 -0.0852 0.287 Uiso 1 1 calc R
C11 C 0.7514(5) 0.3969(6) 0.1250(8) 0.164(3) Uani 1 1 d .
H11A H 0.7411 0.4715 0.0968 0.246 Uiso 1 1 calc R
H11B H 0.7691 0.3927 0.2213 0.246 Uiso 1 1 calc R
H11C H 0.7053 0.3549 0.0823 0.246 Uiso 1 1 calc R
C12 C 0.8844(5) 0.4166(6) 0.1483(8) 0.154(2) Uani 1 1 d .
H12A H 0.8746 0.4916 0.1219 0.232 Uiso 1 1 calc R
H12B H 0.9208 0.3875 0.1180 0.232 Uiso 1 1 calc R
H12C H 0.9047 0.4112 0.2449 0.232 Uiso 1 1 calc R
C13 C 0.8873(9) 0.1232(10) 0.7828(9) 0.206(5) Uani 1 1 d .
H13A H 0.9270 0.1778 0.8214 0.248 Uiso 1 1 calc R
H13B H 0.8488 0.1384 0.8160 0.248 Uiso 1 1 calc R
C14 C 0.9176(10) 0.0296(18) 0.832(2) 0.292(11) Uani 1 1 d .
H14A H 0.9384 0.0319 0.9285 0.439 Uiso 1 1 calc R
H14B H 0.9577 0.0136 0.8038 0.439 Uiso 1 1 calc R
H14C H 0.8790 -0.0260 0.7987 0.439 Uiso 1 1 calc R
C15 C 0.8974(7) 0.4145(6) 0.5734(14) 0.205(5) Uani 1 1 d .
H15A H 0.8664 0.4773 0.5675 0.307 Uiso 1 1 calc R
H15B H 0.9171 0.4192 0.5060 0.307 Uiso 1 1 calc R
H15C H 0.9393 0.4117 0.6614 0.307 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O4 S1 O5 118.4(3)
O4 S1 N1 108.40(16)
O5 S1 N1 108.7(2)
O4 S1 C9 107.6(3)
O5 S1 C9 108.1(3)
N1 S1 C9 104.8(2)
O3 P1 O2 117.5(2)
O3 P1 O1 113.9(2)
O2 P1 O1 102.5(3)
O3 P1 C7 114.28(16)
O2 P1 C7 101.6(2)
O1 P1 C7 105.4(2)
C15 O1 P1 122.6(5)
C13 O2 P1 124.9(7)
C7 N1 S1 124.3(2)
O6 N2 O7 119.1(10)
O6 N2 C4 121.6(13)
O7 N2 C4 119.2(9)
C6 C1 C2 117.3(4)
C6 C1 C7 121.7(3)
C2 C1 C7 121.0(4)
C3 C2 C1 122.7(6)
C2 C3 C4 117.3(5)
C5 C4 C3 122.3(6)
C5 C4 N2 120.4(9)
C3 C4 N2 117.1(7)
C6 C5 C4 118.7(6)
C5 C6 C1 121.6(4)
N1 C7 C1 112.4(3)
N1 C7 C8 112.2(4)
C1 C7 C8 112.1(4)
N1 C7 P1 102.8(2)
C1 C7 P1 108.9(2)
C8 C7 P1 107.9(3)
C11 C9 C12 112.0(6)
C11 C9 C10 114.9(6)
C12 C9 C10 106.5(7)
C11 C9 S1 110.8(4)
C12 C9 S1 107.8(4)
C10 C9 S1 104.3(4)
C14 C13 O2 119.8(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O4 1.415(4)
S1 O5 1.428(4)
S1 N1 1.643(3)
S1 C9 1.813(5)
P1 O3 1.441(3)
P1 O2 1.541(5)
P1 O1 1.561(3)
P1 C7 1.844(4)
O1 C15 1.366(12)
O2 C13 1.481(9)
O6 N2 1.199(12)
O7 N2 1.213(13)
N1 C7 1.470(6)
N2 C4 1.433(11)
C1 C6 1.369(6)
C1 C2 1.392(6)
C1 C7 1.529(6)
C2 C3 1.359(11)
C3 C4 1.369(11)
C4 C5 1.368(9)
C5 C6 1.367(6)
C7 C8 1.559(5)
C9 C11 1.484(10)
C9 C12 1.501(10)
C9 C10 1.557(7)
C13 C14 1.30(2)
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
_geom_hbond_site_symmetry_A
N1 H1A O3 0.86 2.36 2.903(4) 121.5 2_756
N1 H1A O3 0.86 2.62 3.031(3) 110.3 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O3 P1 O1 C15 9.9(9)
O2 P1 O1 C15 137.9(9)
C7 P1 O1 C15 -116.2(8)
O3 P1 O2 C13 33.8(8)
O1 P1 O2 C13 -91.9(7)
C7 P1 O2 C13 159.3(7)
O4 S1 N1 C7 -120.6(3)
O5 S1 N1 C7 9.3(4)
C9 S1 N1 C7 124.7(4)
C6 C1 C2 C3 -2.6(8)
C7 C1 C2 C3 177.7(6)
C1 C2 C3 C4 3.4(10)
C2 C3 C4 C5 -2.8(10)
C2 C3 C4 N2 -177.2(7)
O6 N2 C4 C5 -170.5(9)
O7 N2 C4 C5 7.7(12)
O6 N2 C4 C3 4.1(12)
O7 N2 C4 C3 -177.8(9)
C3 C4 C5 C6 1.5(9)
N2 C4 C5 C6 175.8(6)
C4 C5 C6 C1 -0.8(8)
C2 C1 C6 C5 1.3(7)
C7 C1 C6 C5 -179.1(4)
S1 N1 C7 C1 70.7(3)
S1 N1 C7 C8 -56.8(5)
S1 N1 C7 P1 -172.4(2)
C6 C1 C7 N1 18.2(5)
C2 C1 C7 N1 -162.2(4)
C6 C1 C7 C8 145.6(4)
C2 C1 C7 C8 -34.7(6)
C6 C1 C7 P1 -95.0(4)
C2 C1 C7 P1 84.6(4)
O3 P1 C7 N1 -53.9(3)
O2 P1 C7 N1 178.4(3)
O1 P1 C7 N1 71.9(3)
O3 P1 C7 C1 65.5(3)
O2 P1 C7 C1 -62.2(3)
O1 P1 C7 C1 -168.7(3)
O3 P1 C7 C8 -172.7(4)
O2 P1 C7 C8 59.7(4)
O1 P1 C7 C8 -46.8(4)
O4 S1 C9 C11 -177.3(5)
O5 S1 C9 C11 53.8(5)
N1 S1 C9 C11 -62.1(5)
O4 S1 C9 C12 -54.4(5)
O5 S1 C9 C12 176.6(5)
N1 S1 C9 C12 60.8(5)
O4 S1 C9 C10 58.5(6)
O5 S1 C9 C10 -70.5(6)
N1 S1 C9 C10 173.7(6)
P1 O2 C13 C14 -104.8(15)
