#------------------------------------------------------------------------------
#$Date: 2019-11-28 21:03:14 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244613 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/92/7239239.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_7239239
loop_
_publ_author_name
'Pallikonda, Gangaram'
'Chakravarty, Manab'
_publ_section_title
;
 Triflic acid mediated functionalization of α-hydroxyphosphonates: route
 for sulfonamide phosphonates
;
_journal_issue                   43
_journal_name_full               'RSC Advances'
_journal_page_first              20503
_journal_paper_doi               10.1039/c3ra43823f
_journal_volume                  3
_journal_year                    2013
_chemical_formula_sum            'C20 H26 N O5 P S'
_chemical_formula_weight         423.45
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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                93.9990(10)
_cell_angle_beta                 107.3030(10)
_cell_angle_gamma                116.9270(10)
_cell_formula_units_Z            2
_cell_length_a                   10.8332(8)
_cell_length_b                   10.9777(8)
_cell_length_c                   10.9787(8)
_cell_measurement_reflns_used    6973
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.90
_cell_measurement_theta_min      2.41
_cell_volume                     1078.87(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10411
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0472
_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)+(0.0762P)²+0.4044P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1353
_reflns_number_gt                3257
_reflns_number_total             3780
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra43823f.txt
_cod_data_source_block           platon
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7239239
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 0.30897(6) 0.73952(6) -0.20042(5) 0.04823(19) Uani 1 1 d .
P1 P 0.82320(6) 0.75824(6) 0.16840(6) 0.0498(2) Uani 1 1 d .
O2 O 0.9088(2) 0.8216(2) 0.32043(19) 0.0777(6) Uani 1 1 d .
O3 O 0.94359(19) 0.84760(19) 0.1135(2) 0.0725(5) Uani 1 1 d .
O1 O 0.76055(18) 0.60665(16) 0.12448(18) 0.0608(4) Uani 1 1 d .
O4 O 0.17116(19) 0.6437(2) -0.30520(17) 0.0666(5) Uani 1 1 d .
O5 O 0.3483(2) 0.88356(17) -0.16231(17) 0.0618(4) Uani 1 1 d .
N2 N 0.30345(19) 0.6733(2) -0.07468(17) 0.0435(4) Uani 1 1 d .
C18 C 1.1248(4) 0.8953(4) 0.5100(3) 0.0892(10) Uani 1 1 d .
H18A H 1.1947 0.8686 0.5579 0.134 Uiso 1 1 calc R
H18B H 1.0765 0.9111 0.5649 0.134 Uiso 1 1 calc R
H18C H 1.1765 0.9801 0.4840 0.134 Uiso 1 1 calc R
C17 C 1.0146(4) 0.7843(4) 0.3946(3) 0.0865(9) Uani 1 1 d .
H17A H 1.0636 0.7670 0.3400 0.104 Uiso 1 1 calc R
H17B H 0.9630 0.6983 0.4208 0.104 Uiso 1 1 calc R
C19 C 0.9334(4) 0.8007(4) -0.0143(4) 0.1025(12) Uani 1 1 d .
H19A H 0.8860 0.8410 -0.0745 0.123 Uiso 1 1 calc R
H19B H 0.8701 0.6992 -0.0418 0.123 Uiso 1 1 calc R
C20 C 1.0739(4) 0.8367(5) -0.0236(4) 0.1147(14) Uani 1 1 d .
H20A H 1.0592 0.8025 -0.1125 0.172 Uiso 1 1 calc R
H20B H 1.1203 0.7948 0.0336 0.172 Uiso 1 1 calc R
H20C H 1.1368 0.9372 0.0019 0.172 Uiso 1 1 calc R
C3 C 0.6874(2) 0.8116(2) 0.1323(2) 0.0472(5) Uani 1 1 d .
H3 H 0.7172 0.9069 0.1490 0.057 Uiso 1 1 calc R
C2 C 0.5449(2) 0.7176(2) 0.0820(2) 0.0429(5) Uani 1 1 d .
H2 H 0.5192 0.6236 0.0605 0.051 Uiso 1 1 calc R
C1 C 0.4195(2) 0.7502(2) 0.0563(2) 0.0413(5) Uani 1 1 d .
H1 H 0.4604 0.8513 0.0623 0.050 Uiso 1 1 calc R
C4 C 0.3538(2) 0.7136(2) 0.1623(2) 0.0457(5) Uani 1 1 d .
C5 C 0.2147(3) 0.6014(3) 0.1380(3) 0.0606(6) Uani 1 1 d .
H5 H 0.1556 0.5454 0.0531 0.073 Uiso 1 1 calc R
C6 C 0.1616(4) 0.5709(3) 0.2390(3) 0.0771(8) Uani 1 1 d .
H6 H 0.0671 0.4950 0.2208 0.092 Uiso 1 1 calc R
C7 C 0.2452(4) 0.6499(4) 0.3631(3) 0.0845(10) Uani 1 1 d .
H7 H 0.2093 0.6286 0.4304 0.101 Uiso 1 1 calc R
C8 C 0.3839(4) 0.7622(5) 0.3885(3) 0.0933(11) Uani 1 1 d .
H8 H 0.4424 0.8172 0.4738 0.112 Uiso 1 1 calc R
C9 C 0.4382(3) 0.7948(3) 0.2885(2) 0.0715(8) Uani 1 1 d .
H9 H 0.5321 0.8718 0.3071 0.086 Uiso 1 1 calc R
C10 C 0.4518(3) 0.7376(2) -0.2454(2) 0.0488(5) Uani 1 1 d .
C11 C 0.5716(3) 0.8617(3) -0.2410(2) 0.0603(6) Uani 1 1 d .
H11 H 0.5815 0.9477 -0.2094 0.072 Uiso 1 1 calc R
C12 C 0.6768(3) 0.8566(3) -0.2842(3) 0.0716(8) Uani 1 1 d .
H12 H 0.7574 0.9405 -0.2817 0.086 Uiso 1 1 calc R
C13 C 0.6663(3) 0.7318(3) -0.3308(3) 0.0699(7) Uani 1 1 d .
C14 C 0.5479(4) 0.6084(3) -0.3295(3) 0.0745(8) Uani 1 1 d .
H14 H 0.5409 0.5226 -0.3569 0.089 Uiso 1 1 calc R
C15 C 0.4407(3) 0.6108(3) -0.2882(3) 0.0655(7) Uani 1 1 d .
H15 H 0.3610 0.5270 -0.2893 0.079 Uiso 1 1 calc R
C16 C 0.7788(4) 0.7280(4) -0.3835(4) 0.1016(12) Uani 1 1 d .
H16A H 0.7533 0.6321 -0.4117 0.152 Uiso 1 1 calc R
H16B H 0.8763 0.7784 -0.3156 0.152 Uiso 1 1 calc R
H16C H 0.7783 0.7711 -0.4566 0.152 Uiso 1 1 calc R
H2A H 0.275(3) 0.592(3) -0.092(2) 0.046(7) 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'
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
O4 S1 O5 119.88(11)
O4 S1 N2 105.59(10)
O5 S1 N2 108.03(10)
O4 S1 C10 106.67(11)
O5 S1 C10 107.48(11)
N2 S1 C10 108.83(10)
O1 P1 O3 113.75(10)
O1 P1 O2 115.63(11)
O3 P1 O2 101.91(12)
O1 P1 C3 113.51(10)
O3 P1 C3 108.12(11)
O2 P1 C3 102.71(10)
C17 O2 P1 121.07(19)
C19 O3 P1 121.5(2)
C1 N2 S1 121.53(14)
C1 N2 H2A 114.4(17)
S1 N2 H2A 112.5(18)
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
O2 C17 C18 110.8(3)
O2 C17 H17A 109.5
C18 C17 H17A 109.5
O2 C17 H17B 109.5
C18 C17 H17B 109.5
H17A C17 H17B 108.1
O3 C19 C20 113.7(3)
O3 C19 H19A 108.8
C20 C19 H19A 108.8
O3 C19 H19B 108.8
C20 C19 H19B 108.8
H19A C19 H19B 107.7
C19 C20 H20A 109.5
C19 C20 H20B 109.5
H20A C20 H20B 109.5
C19 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C2 C3 P1 120.48(17)
C2 C3 H3 119.8
P1 C3 H3 119.8
C3 C2 C1 125.11(19)
C3 C2 H2 117.4
C1 C2 H2 117.4
N2 C1 C2 111.95(16)
N2 C1 C4 110.48(17)
C2 C1 C4 108.68(17)
N2 C1 H1 108.6
C2 C1 H1 108.6
C4 C1 H1 108.6
C9 C4 C5 118.3(2)
C9 C4 C1 118.6(2)
C5 C4 C1 123.1(2)
C4 C5 C6 120.7(3)
C4 C5 H5 119.7
C6 C5 H5 119.7
C7 C6 C5 120.9(3)
C7 C6 H6 119.5
C5 C6 H6 119.5
C6 C7 C8 119.0(3)
C6 C7 H7 120.5
C8 C7 H7 120.5
C7 C8 C9 120.8(3)
C7 C8 H8 119.6
C9 C8 H8 119.6
C4 C9 C8 120.2(3)
C4 C9 H9 119.9
C8 C9 H9 119.9
C11 C10 C15 120.0(2)
C11 C10 S1 120.40(19)
C15 C10 S1 119.57(18)
C10 C11 C12 119.1(3)
C10 C11 H11 120.4
C12 C11 H11 120.4
C13 C12 C11 122.1(3)
C13 C12 H12 119.0
C11 C12 H12 119.0
C12 C13 C14 117.9(3)
C12 C13 C16 121.4(3)
C14 C13 C16 120.8(3)
C15 C14 C13 121.1(3)
C15 C14 H14 119.5
C13 C14 H14 119.5
C14 C15 C10 119.8(2)
C14 C15 H15 120.1
C10 C15 H15 120.1
C13 C16 H16A 109.5
C13 C16 H16B 109.5
H16A C16 H16B 109.5
C13 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O4 1.4305(17)
S1 O5 1.4312(17)
S1 N2 1.6085(19)
S1 C10 1.766(2)
P1 O1 1.4604(17)
P1 O3 1.5547(19)
P1 O2 1.569(2)
P1 C3 1.769(2)
O2 C17 1.436(3)
O3 C19 1.415(4)
N2 C1 1.468(3)
N2 H2A 0.79(2)
C18 C17 1.443(4)
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
C17 H17A 0.9700
C17 H17B 0.9700
C19 C20 1.427(5)
C19 H19A 0.9700
C19 H19B 0.9700
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
C3 C2 1.313(3)
C3 H3 0.9300
C2 C1 1.510(3)
C2 H2 0.9300
C1 C4 1.523(3)
C1 H1 0.9800
C4 C9 1.373(3)
C4 C5 1.376(3)
C5 C6 1.389(4)
C5 H5 0.9300
C6 C7 1.348(5)
C6 H6 0.9300
C7 C8 1.371(5)
C7 H7 0.9300
C8 C9 1.389(4)
C8 H8 0.9300
C9 H9 0.9300
C10 C11 1.376(3)
C10 C15 1.378(3)
C11 C12 1.379(4)
C11 H11 0.9300
C12 C13 1.370(4)
C12 H12 0.9300
C13 C14 1.386(4)
C13 C16 1.511(4)
C14 C15 1.376(4)
C14 H14 0.9300
C15 H15 0.9300
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
