#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:48:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178445 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/66/4026662.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_4026662
loop_
_publ_author_name
'Francisco Alonso'
'Yanina Moglie'
'Gabriel Radivoy'
'Miguel Yus'
_publ_section_title
;
 Multicomponent Click Synthesis of 1,2,3-Triazoles from Epoxides in Water
 Catalyzed by Copper Nanoparticles on Activated Carbon
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8394
_journal_page_last               8405
_journal_paper_doi               10.1021/jo2016339
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H17 N3 O3 S'
_chemical_formula_sum            'C17 H17 N3 O3 S'
_chemical_formula_weight         343.40
_chemical_name_systematic
; 

 ? 

;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 92.439(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.6956(15)
_cell_length_b                   5.5642(9)
_cell_length_c                   17.425(3)
_cell_measurement_reflns_used    779
_cell_measurement_temperature    295(1)
_cell_measurement_theta_max      20.6
_cell_measurement_theta_min      2.34
_cell_volume                     842.3(2)
_computing_cell_refinement       'Bruker SMART V5.625'
_computing_data_collection       'Bruker SMART V5.625'
_computing_data_reduction        'Bruker SAINT V6.28A'
_computing_molecular_graphics    'SHELXTL  Rel. 6.12/V (Siemens, 1996)'
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;SIR92 (Altomare, Cascarano, Giacovazzo & Guagliardi, 1993)

;
_diffrn_ambient_temperature      295(1)
_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  0.0544
_diffrn_reflns_av_sigmaI/netI    0.0910
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7125
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_correction_T_min  0.8751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker/Siemens SADABS V2.03'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2960
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0479
_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)+(0.0210P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0948
_reflns_number_gt                1904
_reflns_number_total             2960
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo2016339_si_004.cif
_cod_data_source_block           x
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4026662
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
N1 N 0.8811(4) -0.3093(5) 0.81306(19) 0.0549(8) Uani 1 1 d .
N2 N 0.9476(4) -0.2408(5) 0.75039(19) 0.0559(9) Uani 1 1 d .
N3 N 0.9809(3) -0.0035(5) 0.75974(16) 0.0439(8) Uani 1 1 d .
C1 C 0.9386(3) 0.0740(7) 0.82859(19) 0.0442(9) Uani 1 1 d .
H1 H 0.9508 0.2276 0.8490 0.053 Uiso 1 1 calc R
C2 C 0.8738(4) -0.1214(7) 0.8625(2) 0.0443(9) Uani 1 1 d .
C3 C 0.8070(4) -0.1396(7) 0.9378(2) 0.0477(10) Uani 1 1 d .
C4 C 0.7122(4) -0.3280(7) 0.9563(2) 0.0595(11) Uani 1 1 d .
H4 H 0.6912 -0.4478 0.9201 0.071 Uiso 1 1 calc R
C5 C 0.6482(5) -0.3427(8) 1.0269(3) 0.0719(13) Uani 1 1 d .
H5 H 0.5842 -0.4708 1.0381 0.086 Uiso 1 1 calc R
C6 C 0.6790(5) -0.1679(10) 1.0805(2) 0.0723(13) Uani 1 1 d .
H6 H 0.6370 -0.1782 1.1286 0.087 Uiso 1 1 calc R
C7 C 0.7713(5) 0.0220(10) 1.0635(2) 0.0741(12) Uani 1 1 d .
H7 H 0.7917 0.1404 1.1002 0.089 Uiso 1 1 calc R
C8 C 0.8343(4) 0.0393(9) 0.9926(2) 0.0619(10) Uani 1 1 d .
H8 H 0.8952 0.1709 0.9813 0.074 Uiso 1 1 calc R
C9 C 1.0642(3) 0.1286(6) 0.70209(19) 0.0436(9) Uani 1 1 d .
H9 H 1.0359 0.2983 0.7066 0.052 Uiso 1 1 calc R
C10 C 1.2366(4) 0.1124(6) 0.71519(19) 0.0444(9) Uani 1 1 d .
C11 C 1.3082(5) -0.0805(8) 0.7518(2) 0.0622(12) Uani 1 1 d .
H11 H 1.2488 -0.2064 0.7695 0.075 Uiso 1 1 calc R
C12 C 1.4673(5) -0.0894(10) 0.7627(3) 0.0811(15) Uani 1 1 d .
H12 H 1.5137 -0.2179 0.7888 0.097 Uiso 1 1 calc R
C13 C 1.5544(5) 0.0897(13) 0.7352(3) 0.0906(17) Uani 1 1 d .
H13 H 1.6610 0.0821 0.7417 0.109 Uiso 1 1 calc R
C14 C 1.4877(5) 0.2812(10) 0.6981(3) 0.0812(15) Uani 1 1 d .
H14 H 1.5486 0.4035 0.6794 0.097 Uiso 1 1 calc R
C15 C 1.3280(5) 0.2935(8) 0.6882(2) 0.0636(12) Uani 1 1 d .
H15 H 1.2827 0.4250 0.6632 0.076 Uiso 1 1 calc R
C16 C 1.0180(3) 0.0499(8) 0.62204(17) 0.0492(9) Uani 1 1 d .
H16A H 1.0849 0.1223 0.5853 0.059 Uiso 1 1 calc R
H16B H 1.0252 -0.1235 0.6177 0.059 Uiso 1 1 calc R
O1 O 0.8600(2) 0.1282(4) 0.60726(13) 0.0520(7) Uani 1 1 d .
S1 S 0.77539(11) 0.04678(17) 0.52992(6) 0.0538(3) Uani 1 1 d .
O2 O 0.6495(3) 0.2079(5) 0.51955(18) 0.0837(10) Uani 1 1 d .
O3 O 0.8865(3) 0.0280(6) 0.47180(13) 0.0664(7) Uani 1 1 d .
C17 C 0.7075(5) -0.2366(7) 0.5520(3) 0.0738(14) Uani 1 1 d .
H17A H 0.6375 -0.2244 0.5929 0.111 Uiso 1 1 calc R
H17B H 0.7924 -0.3380 0.5677 0.111 Uiso 1 1 calc R
H17C H 0.6551 -0.3045 0.5075 0.111 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
N2 N1 C2 109.8(3)
N1 N2 N3 106.3(3)
C1 N3 N2 110.7(3)
C1 N3 C9 128.0(3)
N2 N3 C9 121.0(3)
N3 C1 C2 105.3(3)
N3 C1 H1 127.4
C2 C1 H1 127.4
N1 C2 C1 107.9(3)
N1 C2 C3 123.2(3)
C1 C2 C3 128.9(4)
C4 C3 C8 117.9(4)
C4 C3 C2 121.8(4)
C8 C3 C2 120.3(4)
C5 C4 C3 121.5(4)
C5 C4 H4 119.2
C3 C4 H4 119.2
C6 C5 C4 119.6(4)
C6 C5 H5 120.2
C4 C5 H5 120.2
C7 C6 C5 120.1(4)
C7 C6 H6 119.9
C5 C6 H6 119.9
C6 C7 C8 120.6(4)
C6 C7 H7 119.7
C8 C7 H7 119.7
C7 C8 C3 120.2(4)
C7 C8 H8 119.9
C3 C8 H8 119.9
N3 C9 C16 111.8(3)
N3 C9 C10 112.6(3)
C16 C9 C10 110.4(3)
N3 C9 H9 107.3
C16 C9 H9 107.3
C10 C9 H9 107.3
C15 C10 C11 118.1(3)
C15 C10 C9 119.2(3)
C11 C10 C9 122.7(3)
C10 C11 C12 121.1(4)
C10 C11 H11 119.5
C12 C11 H11 119.5
C13 C12 C11 119.7(4)
C13 C12 H12 120.2
C11 C12 H12 120.2
C12 C13 C14 120.8(4)
C12 C13 H13 119.6
C14 C13 H13 119.6
C13 C14 C15 119.9(4)
C13 C14 H14 120.1
C15 C14 H14 120.1
C10 C15 C14 120.5(4)
C10 C15 H15 119.7
C14 C15 H15 119.7
O1 C16 C9 106.9(2)
O1 C16 H16A 110.3
C9 C16 H16A 110.3
O1 C16 H16B 110.3
C9 C16 H16B 110.3
H16A C16 H16B 108.6
C16 O1 S1 118.0(2)
O2 S1 O3 119.68(19)
O2 S1 O1 104.89(15)
O3 S1 O1 108.75(13)
O2 S1 C17 109.6(2)
O3 S1 C17 109.7(2)
O1 S1 C17 102.89(18)
S1 C17 H17A 109.5
S1 C17 H17B 109.5
H17A C17 H17B 109.5
S1 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 N2 1.314(4)
N1 C2 1.357(4)
N2 N3 1.360(4)
N3 C1 1.341(4)
N3 C9 1.461(4)
C1 C2 1.370(5)
C1 H1 0.9300
C2 C3 1.461(4)
C3 C4 1.380(5)
C3 C8 1.393(6)
C4 C5 1.375(5)
C4 H4 0.9300
C5 C6 1.367(6)
C5 H5 0.9300
C6 C7 1.367(6)
C6 H6 0.9300
C7 C8 1.376(5)
C7 H7 0.9300
C8 H8 0.9300
C9 C16 1.500(4)
C9 C10 1.510(4)
C9 H9 0.9800
C10 C15 1.378(5)
C10 C11 1.383(5)
C11 C12 1.390(5)
C11 H11 0.9300
C12 C13 1.351(7)
C12 H12 0.9300
C13 C14 1.364(6)
C13 H13 0.9300
C14 C15 1.394(5)
C14 H14 0.9300
C15 H15 0.9300
C16 O1 1.454(3)
C16 H16A 0.9700
C16 H16B 0.9700
O1 S1 1.574(2)
S1 O2 1.421(3)
S1 O3 1.433(3)
S1 C17 1.733(4)
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
