#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:22:32 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180390 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/59/7205908.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_7205908
loop_
_publ_author_name
'Shaabani, Ahmad'
'Sarvary, Afshin'
'Ghasemi, Sabrieh'
'Rezayan, Ali Hossein'
'Ghadari, Rahim'
'Ng, Seik Weng'
_publ_section_title
;
 An environmentally benign approach for the synthesis of bifunctional
 sulfonamide-amide compounds via isocyanide-based multicomponent
 reactions
;
_journal_issue                   3
_journal_name_full               'Green Chemistry'
_journal_page_first              582
_journal_paper_doi               10.1039/c0gc00442a
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C24 H30 N2 O7 S'
_chemical_formula_weight         490.56
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 117.989(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2071(8)
_cell_length_b                   23.3231(15)
_cell_length_c                   11.1208(8)
_cell_measurement_reflns_used    5768
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.2
_cell_measurement_theta_min      2.2
_cell_volume                     2566.8(3)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 software (Bruker, 2008)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'ω 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  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24249
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.9586
_exptl_absorpt_correction_T_min  0.9428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Irregular
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         5904
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0618
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0547P)²+2.6886P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1576
_refine_ls_wR_factor_ref         0.1768
_reflns_number_gt                4121
_reflns_number_total             5904
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c0gc00442a.txt
_cod_data_source_block           b
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7205908
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
S1 S 0.23322(7) 0.58029(3) 0.51711(7) 0.0451(2) Uani 1 1 d . . .
O1 O 0.0928(2) 0.57305(10) 0.4793(3) 0.0631(6) Uani 1 1 d . . .
O2 O 0.3257(3) 0.59846(10) 0.6517(2) 0.0632(6) Uani 1 1 d . . .
O3 O 0.2222(2) 0.42561(10) 0.2158(2) 0.0573(6) Uani 1 1 d . . .
O4 O 0.4080(2) 0.47492(10) 0.3540(2) 0.0558(6) Uani 1 1 d . . .
O5 O -0.0549(2) 0.43502(11) 0.1918(2) 0.0679(7) Uani 1 1 d . . .
O6 O 0.0238(3) 0.35082(11) 0.2937(3) 0.0775(8) Uani 1 1 d . . .
O7 O 0.3336(2) 0.38593(11) 0.5243(2) 0.0651(7) Uani 1 1 d . . .
N1 N 0.2865(2) 0.51882(9) 0.4955(2) 0.0392(5) Uani 1 1 d . . .
H1 H 0.3639 0.5062 0.5554 0.047 Uiso 1 1 calc R . .
N2 N 0.1964(2) 0.38594(10) 0.6206(2) 0.0448(5) Uani 1 1 d . . .
H2 H 0.1193 0.3968 0.6115 0.054 Uiso 1 1 calc R . .
C1 C 0.2419(3) 0.62818(11) 0.3993(3) 0.0413(6) Uani 1 1 d . . .
C2 C 0.1309(3) 0.66075(14) 0.3150(3) 0.0589(8) Uani 1 1 d . . .
H2A H 0.0491 0.6559 0.3162 0.071 Uiso 1 1 calc R . .
C3 C 0.1424(4) 0.70048(16) 0.2291(4) 0.0695(10) Uani 1 1 d . . .
H3 H 0.0681 0.7229 0.1737 0.083 Uiso 1 1 calc R . .
C4 C 0.2629(4) 0.70760(14) 0.2239(3) 0.0595(8) Uani 1 1 d . . .
C5 C 0.3713(3) 0.67404(14) 0.3072(3) 0.0578(8) Uani 1 1 d . . .
H5 H 0.4522 0.6778 0.3036 0.069 Uiso 1 1 calc R . .
C6 C 0.3627(3) 0.63499(13) 0.3959(3) 0.0511(7) Uani 1 1 d . . .
H6 H 0.4378 0.6134 0.4531 0.061 Uiso 1 1 calc R . .
C7 C 0.2736(5) 0.75102(19) 0.1294(5) 0.0980(15) Uani 1 1 d . . .
H7A H 0.3671 0.7584 0.1566 0.147 Uiso 1 1 calc R . .
H7B H 0.2303 0.7860 0.1331 0.147 Uiso 1 1 calc R . .
H7C H 0.2302 0.7364 0.0380 0.147 Uiso 1 1 calc R . .
C8 C 0.2040(3) 0.48453(11) 0.3749(3) 0.0377(6) Uani 1 1 d . . .
H8 H 0.1368 0.5099 0.3063 0.045 Uiso 1 1 calc R . .
C9 C 0.1277(3) 0.43827(11) 0.4113(3) 0.0385(6) Uani 1 1 d . . .
H9 H 0.0754 0.4582 0.4487 0.046 Uiso 1 1 calc R . .
C10 C 0.2933(3) 0.46092(12) 0.3174(3) 0.0424(6) Uani 1 1 d . . .
C11 C 0.2879(4) 0.39892(18) 0.1441(4) 0.0702(10) Uani 1 1 d . . .
H11A H 0.3375 0.3651 0.1924 0.084 Uiso 1 1 calc R . .
H11B H 0.3503 0.4255 0.1359 0.084 Uiso 1 1 calc R . .
C12 C 0.1771(5) 0.3831(2) 0.0067(4) 0.0898(13) Uani 1 1 d . . .
H12A H 0.2137 0.3613 -0.0415 0.135 Uiso 1 1 calc R . .
H12B H 0.1355 0.4174 -0.0435 0.135 Uiso 1 1 calc R . .
H12C H 0.1107 0.3605 0.0168 0.135 Uiso 1 1 calc R . .
C13 C 0.0287(3) 0.40175(15) 0.2932(3) 0.0508(7) Uani 1 1 d . . .
C14 C -0.1550(5) 0.4046(2) 0.0703(4) 0.1034(17) Uani 1 1 d . . .
H14A H -0.1137 0.3715 0.0518 0.124 Uiso 1 1 calc R . .
H14B H -0.2294 0.3914 0.0848 0.124 Uiso 1 1 calc R . .
C15 C -0.2031(6) 0.4436(2) -0.0416(5) 0.131(2) Uani 1 1 d . . .
H15A H -0.2673 0.4245 -0.1228 0.197 Uiso 1 1 calc R . .
H15B H -0.1285 0.4569 -0.0541 0.197 Uiso 1 1 calc R . .
H15C H -0.2457 0.4757 -0.0233 0.197 Uiso 1 1 calc R . .
C16 C 0.2290(3) 0.40031(11) 0.5236(3) 0.0402(6) Uani 1 1 d . . .
C17 C 0.2830(3) 0.35333(15) 0.7395(3) 0.0534(8) Uani 1 1 d . . .
C18 C 0.2572(5) 0.29561(17) 0.7439(4) 0.0769(12) Uani 1 1 d . . .
C19 C 0.3412(8) 0.2665(3) 0.8642(7) 0.123(2) Uani 1 1 d . . .
H19 H 0.3278 0.2276 0.8717 0.148 Uiso 1 1 calc R . .
C20 C 0.4422(7) 0.2945(4) 0.9704(7) 0.139(3) Uani 1 1 d . . .
H20 H 0.4960 0.2743 1.0498 0.167 Uiso 1 1 calc R . .
C21 C 0.4666(5) 0.3512(3) 0.9638(5) 0.115(2) Uani 1 1 d . . .
H21 H 0.5372 0.3691 1.0376 0.138 Uiso 1 1 calc R . .
C22 C 0.3861(4) 0.3823(2) 0.8467(4) 0.0777(12) Uani 1 1 d . . .
C23 C 0.4083(6) 0.4452(3) 0.8391(5) 0.122(2) Uani 1 1 d . . .
H23A H 0.3250 0.4654 0.8126 0.183 Uiso 1 1 calc R . .
H23B H 0.4392 0.4520 0.7731 0.183 Uiso 1 1 calc R . .
H23C H 0.4750 0.4587 0.9266 0.183 Uiso 1 1 calc R . .
C24 C 0.1461(6) 0.26576(19) 0.6246(6) 0.1130(18) Uani 1 1 d . . .
H24A H 0.0713 0.2915 0.5791 0.170 Uiso 1 1 calc R . .
H24B H 0.1173 0.2328 0.6558 0.170 Uiso 1 1 calc R . .
H24C H 0.1786 0.2539 0.5625 0.170 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'
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
O2 S1 O1 119.89(15) . . ?
O2 S1 N1 106.40(13) . . ?
O1 S1 N1 106.47(13) . . ?
O2 S1 C1 109.02(14) . . ?
O1 S1 C1 107.04(14) . . ?
N1 S1 C1 107.43(12) . . ?
C10 O3 C11 118.5(2) . . ?
C13 O5 C14 115.4(3) . . ?
C8 N1 S1 120.29(17) . . ?
C16 N2 C17 123.7(2) . . ?
C6 C1 C2 120.0(3) . . ?
C6 C1 S1 119.4(2) . . ?
C2 C1 S1 120.5(2) . . ?
C3 C2 C1 119.5(3) . . ?
C2 C3 C4 121.2(3) . . ?
C5 C4 C3 118.3(3) . . ?
C5 C4 C7 121.2(4) . . ?
C3 C4 C7 120.5(3) . . ?
C4 C5 C6 121.4(3) . . ?
C5 C6 C1 119.6(3) . . ?
N1 C8 C10 109.1(2) . . ?
N1 C8 C9 109.4(2) . . ?
C10 C8 C9 114.3(2) . . ?
C16 C9 C13 110.2(2) . . ?
C16 C9 C8 109.3(2) . . ?
C13 C9 C8 115.7(2) . . ?
O4 C10 O3 125.6(3) . . ?
O4 C10 C8 124.9(3) . . ?
O3 C10 C8 109.4(2) . . ?
O3 C11 C12 105.9(3) . . ?
O6 C13 O5 124.9(3) . . ?
O6 C13 C9 124.9(3) . . ?
O5 C13 C9 110.1(3) . . ?
C15 C14 O5 107.8(4) . . ?
O7 C16 N2 123.7(3) . . ?
O7 C16 C9 120.9(2) . . ?
N2 C16 C9 115.4(2) . . ?
C18 C17 C22 123.3(3) . . ?
C18 C17 N2 119.1(3) . . ?
C22 C17 N2 117.6(3) . . ?
C17 C18 C19 116.7(5) . . ?
C17 C18 C24 121.5(4) . . ?
C19 C18 C24 121.9(5) . . ?
C20 C19 C18 120.7(6) . . ?
C21 C20 C19 121.8(5) . . ?
C20 C21 C22 120.0(6) . . ?
C17 C22 C21 117.6(5) . . ?
C17 C22 C23 121.5(4) . . ?
C21 C22 C23 120.9(5) . . ?
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
S1 O2 1.428(2) . ?
S1 O1 1.435(2) . ?
S1 N1 1.614(2) . ?
S1 C1 1.759(3) . ?
O3 C10 1.321(3) . ?
O3 C11 1.455(4) . ?
O4 C10 1.197(3) . ?
O5 C13 1.327(4) . ?
O5 C14 1.471(4) . ?
O6 C13 1.189(4) . ?
O7 C16 1.216(3) . ?
N1 C8 1.460(3) . ?
N2 C16 1.333(3) . ?
N2 C17 1.437(4) . ?
C1 C6 1.381(4) . ?
C1 C2 1.381(4) . ?
C2 C3 1.380(5) . ?
C3 C4 1.388(5) . ?
C4 C5 1.375(5) . ?
C4 C7 1.505(5) . ?
C5 C6 1.379(4) . ?
C8 C10 1.521(4) . ?
C8 C9 1.544(4) . ?
C9 C16 1.517(4) . ?
C9 C13 1.521(4) . ?
C11 C12 1.494(5) . ?
C14 C15 1.428(7) . ?
C17 C18 1.382(5) . ?
C17 C22 1.386(5) . ?
C18 C19 1.399(6) . ?
C18 C24 1.498(7) . ?
C19 C20 1.359(9) . ?
C20 C21 1.359(10) . ?
C21 C22 1.391(6) . ?
C22 C23 1.497(7) . ?
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 H1 O4 0.86 2.31 3.027(3) 141.3 3_666
N2 H2 O1 0.86 2.22 3.046(3) 162.0 3_566
