#------------------------------------------------------------------------------
#$Date: 2019-11-23 11:33:54 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233102 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/55/7235522.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_7235522
loop_
_publ_author_name
'Singhamahapatra, Anadi'
'Sahoo, Laxminarayan'
'Varghese, Babu'
'Loganathan, Duraikkannu'
_publ_section_title
;
 Synthesis of glycopeptoid sulfonamides diversifying N-glycopeptide
 linkage region mimics
;
_journal_issue                   35
_journal_name_full               'RSC Advances'
_journal_page_first              18038
_journal_paper_doi               10.1039/c4ra01009d
_journal_volume                  4
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H17 N O4 S'
_chemical_formula_weight         295.35
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.53780(10)
_cell_length_b                   12.7943(3)
_cell_length_c                   17.9426(4)
_cell_measurement_reflns_used    2230
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.2
_cell_measurement_theta_min      2.6
_cell_volume                     1500.84(5)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_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  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9289
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(7)
_refine_ls_extinction_coef       0.026(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0469P)²+0.1769P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0775
_reflns_number_gt                2487
_reflns_number_total             2616
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra01009d1.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7235522
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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
C1 C 0.1954(4) 0.4615(2) 0.24439(10) 0.0710(6) Uani 1 1 d .
H1A H 0.3261 0.4402 0.2635 0.106 Uiso 1 1 calc R
H1B H 0.1126 0.4008 0.2353 0.106 Uiso 1 1 calc R
H1C H 0.1286 0.5056 0.2802 0.106 Uiso 1 1 calc R
C2 C 0.2553(2) 0.38417(11) 0.05328(7) 0.0349(3) Uani 1 1 d .
H2 H 0.1087 0.3999 0.0557 0.042 Uiso 1 1 calc R
C3 C 0.2819(2) 0.27105(12) 0.07727(9) 0.0403(4) Uani 1 1 d .
C4 C 0.2469(5) 0.15646(15) 0.18024(13) 0.0752(7) Uani 1 1 d .
H4A H 0.1701 0.1041 0.1541 0.113 Uiso 1 1 calc R
H4B H 0.2035 0.1588 0.2313 0.113 Uiso 1 1 calc R
H4C H 0.3899 0.1397 0.1781 0.113 Uiso 1 1 calc R
C5 C 0.3234(3) 0.40154(13) -0.02757(9) 0.0435(4) Uani 1 1 d .
H5A H 0.4663 0.3824 -0.0325 0.052 Uiso 1 1 calc R
H5B H 0.2445 0.3564 -0.0601 0.052 Uiso 1 1 calc R
C6 C 0.2956(3) 0.51375(13) -0.05175(8) 0.0415(4) Uani 1 1 d .
C7 C 0.1021(3) 0.55314(17) -0.06475(11) 0.0543(5) Uani 1 1 d .
H7 H -0.0115 0.5101 -0.0591 0.065 Uiso 1 1 calc R
C8 C 0.0761(4) 0.6562(2) -0.08606(12) 0.0696(6) Uani 1 1 d .
H8 H -0.0547 0.6817 -0.0953 0.084 Uiso 1 1 calc R
C9 C 0.2408(4) 0.72063(16) -0.09368(11) 0.0711(6) Uani 1 1 d .
H9 H 0.2221 0.7899 -0.1079 0.085 Uiso 1 1 calc R
C10 C 0.4330(4) 0.68348(18) -0.08047(12) 0.0671(6) Uani 1 1 d .
H10 H 0.5454 0.7275 -0.0855 0.081 Uiso 1 1 calc R
C11 C 0.4605(3) 0.58051(17) -0.05969(11) 0.0555(5) Uani 1 1 d .
H11 H 0.5920 0.5557 -0.0509 0.067 Uiso 1 1 calc R
C12 C 0.5818(3) 0.44759(14) 0.11362(10) 0.0457(4) Uani 1 1 d .
H12A H 0.6421 0.4281 0.0662 0.055 Uiso 1 1 calc R
H12B H 0.6356 0.5157 0.1272 0.055 Uiso 1 1 calc R
C13 C 0.6453(3) 0.37162(17) 0.17003(12) 0.0571(5) Uani 1 1 d .
C14 C 0.6942(4) 0.3112(2) 0.21540(17) 0.0908(9) Uani 1 1 d .
N1 N 0.35883(19) 0.45626(10) 0.10411(7) 0.0349(3) Uani 1 1 d .
O1 O 0.3564(3) 0.61862(12) 0.17611(10) 0.0806(5) Uani 1 1 d .
O2 O 0.0325(2) 0.54660(12) 0.12864(8) 0.0615(4) Uani 1 1 d .
O3 O 0.3519(2) 0.20283(10) 0.03921(8) 0.0596(4) Uani 1 1 d .
O4 O 0.2126(2) 0.25701(10) 0.14600(7) 0.0559(3) Uani 1 1 d .
S1 S 0.22980(7) 0.53053(3) 0.16074(2) 0.04582(15) Uani 1 1 d .
H14 H 0.720(5) 0.266(2) 0.2497(18) 0.119(11) 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'
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
S1 C1 H1A 109.5
S1 C1 H1B 109.5
H1A C1 H1B 109.5
S1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 C3 111.77(12)
N1 C2 C5 111.35(13)
C3 C2 C5 111.87(13)
N1 C2 H2 107.2
C3 C2 H2 107.2
C5 C2 H2 107.2
O3 C3 O4 124.17(16)
O3 C3 C2 125.14(15)
O4 C3 C2 110.68(14)
O4 C4 H4A 109.5
O4 C4 H4B 109.5
H4A C4 H4B 109.5
O4 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
C6 C5 C2 111.99(14)
C6 C5 H5A 109.2
C2 C5 H5A 109.2
C6 C5 H5B 109.2
C2 C5 H5B 109.2
H5A C5 H5B 107.9
C7 C6 C11 118.11(17)
C7 C6 C5 120.33(16)
C11 C6 C5 121.54(17)
C6 C7 C8 120.4(2)
C6 C7 H7 119.8
C8 C7 H7 119.8
C9 C8 C7 120.5(2)
C9 C8 H8 119.8
C7 C8 H8 119.8
C8 C9 C10 119.98(19)
C8 C9 H9 120.0
C10 C9 H9 120.0
C9 C10 C11 120.0(2)
C9 C10 H10 120.0
C11 C10 H10 120.0
C10 C11 C6 121.0(2)
C10 C11 H11 119.5
C6 C11 H11 119.5
C13 C12 N1 114.28(15)
C13 C12 H12A 108.7
N1 C12 H12A 108.7
C13 C12 H12B 108.7
N1 C12 H12B 108.7
H12A C12 H12B 107.6
C14 C13 C12 179.3(3)
C13 C14 H14 176(2)
C2 N1 C12 118.88(13)
C2 N1 S1 121.17(10)
C12 N1 S1 119.02(11)
C3 O4 C4 117.61(16)
O1 S1 O2 119.26(11)
O1 S1 N1 106.36(9)
O2 S1 N1 107.50(7)
O1 S1 C1 107.87(12)
O2 S1 C1 107.54(10)
N1 S1 C1 107.85(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 S1 1.756(2)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 N1 1.4631(19)
C2 C3 1.520(2)
C2 C5 1.534(2)
C2 H2 0.9800
C3 O3 1.199(2)
C3 O4 1.326(2)
C4 O4 1.443(2)
C4 H4A 0.9600
C4 H4B 0.9600
C4 H4C 0.9600
C5 C6 1.511(2)
C5 H5A 0.9700
C5 H5B 0.9700
C6 C7 1.382(3)
C6 C11 1.383(3)
C7 C8 1.384(3)
C7 H7 0.9300
C8 C9 1.363(4)
C8 H8 0.9300
C9 C10 1.364(3)
C9 H9 0.9300
C10 C11 1.381(3)
C10 H10 0.9300
C11 H11 0.9300
C12 C13 1.463(3)
C12 N1 1.472(2)
C12 H12A 0.9700
C12 H12B 0.9700
C13 C14 1.167(3)
C14 H14 0.86(3)
N1 S1 1.6269(13)
O1 S1 1.4253(16)
O2 S1 1.4275(15)
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
C1 H1B O4 0.96 2.53 3.158(3) 123.4 .
C2 H2 O2 0.98 2.34 2.8755(19) 113.4 .
C12 H12B O2 0.97 2.63 3.219(2) 119.8 1_655
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
N1 C2 C3 O3 -123.91(18)
C5 C2 C3 O3 1.7(2)
N1 C2 C3 O4 57.48(17)
C5 C2 C3 O4 -176.88(14)
N1 C2 C5 C6 -54.55(19)
C3 C2 C5 C6 179.58(14)
C2 C5 C6 C7 -72.4(2)
C2 C5 C6 C11 105.97(19)
C11 C6 C7 C8 0.8(3)
C5 C6 C7 C8 179.25(17)
C6 C7 C8 C9 -0.8(3)
C7 C8 C9 C10 0.2(3)
C8 C9 C10 C11 0.3(3)
C9 C10 C11 C6 -0.2(3)
C7 C6 C11 C10 -0.4(3)
C5 C6 C11 C10 -178.77(17)
N1 C12 C13 C14 -32(25)
C3 C2 N1 C12 60.77(17)
C5 C2 N1 C12 -65.15(18)
C3 C2 N1 S1 -108.09(13)
C5 C2 N1 S1 125.99(12)
C13 C12 N1 C2 -86.05(19)
C13 C12 N1 S1 83.05(18)
O3 C3 O4 C4 8.0(3)
C2 C3 O4 C4 -173.37(17)
C2 N1 S1 O1 -154.67(13)
C12 N1 S1 O1 36.49(15)
C2 N1 S1 O2 -25.86(14)
C12 N1 S1 O2 165.30(13)
C2 N1 S1 C1 89.83(15)
C12 N1 S1 C1 -79.01(15)
