#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:32:55 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180186 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/82/7108249.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_7108249
loop_
_publ_author_name
'Shaoyu Li'
'Jie Wu'
_publ_section_title
;
 A copper(I)-catalyzed reaction of 2-(2-ethynylphenyl)oxirane, sulfonyl
 azide, with 2-isocyanoacetate
;
_journal_name_full               Chem.Commun.
_journal_page_first              8973
_journal_paper_doi               10.1039/c2cc34591a
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C20 H21 N O3 S'
_chemical_formula_weight         355.44
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 116.951(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.000(16)
_cell_length_b                   7.953(8)
_cell_length_c                   16.368(17)
_cell_measurement_reflns_used    1003
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.274
_cell_measurement_theta_min      2.406
_cell_volume                     1857(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0734
_diffrn_reflns_av_sigmaI/netI    0.0577
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7386
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.9535
_exptl_absorpt_correction_T_min  0.9358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       0.111(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3257
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0755
_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)+(0.1173P)²+0.1646P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1763
_refine_ls_wR_factor_ref         0.1899
_reflns_number_gt                2557
_reflns_number_total             3257
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc34591a.txt
_cod_data_source_block           a20229a
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7108249
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
N1 N -0.05549(15) 0.4458(3) 0.08581(13) 0.0583(6) Uani 1 1 d .
O1 O -0.19355(15) 0.3267(3) 0.10312(16) 0.0842(7) Uani 1 1 d .
O2 O -0.21221(15) 0.5558(3) -0.00434(13) 0.0897(7) Uani 1 1 d .
O3 O 0.00778(11) 0.3605(2) 0.23522(10) 0.0580(5) Uani 1 1 d .
S1 S -0.15852(4) 0.47857(9) 0.08298(4) 0.0630(3) Uani 1 1 d .
C1 C 0.01400(17) 0.3875(3) 0.15747(15) 0.0498(6) Uani 1 1 d .
C2 C 0.10366(18) 0.3471(3) 0.15508(18) 0.0585(6) Uani 1 1 d .
H2A H 0.1556 0.3978 0.2073 0.070 Uiso 1 1 calc R
H2B H 0.1028 0.3926 0.0997 0.070 Uiso 1 1 calc R
C3 C 0.11638(17) 0.1602(3) 0.15740(19) 0.0605(7) Uani 1 1 d .
C4 C 0.1164(2) 0.0767(5) 0.0834(3) 0.0930(10) Uani 1 1 d .
H4 H 0.1066 0.1354 0.0306 0.112 Uiso 1 1 calc R
C5 C 0.1314(3) -0.0953(7) 0.0884(4) 0.1252(18) Uani 1 1 d .
H5 H 0.1313 -0.1516 0.0386 0.150 Uiso 1 1 calc R
C6 C 0.1460(3) -0.1830(5) 0.1647(5) 0.126(2) Uani 1 1 d .
H6 H 0.1562 -0.2984 0.1668 0.151 Uiso 1 1 calc R
C7 C 0.1461(2) -0.1023(4) 0.2397(3) 0.0988(13) Uani 1 1 d .
H7 H 0.1569 -0.1633 0.2921 0.119 Uiso 1 1 calc R
C8 C 0.12962(17) 0.0720(3) 0.2368(2) 0.0656(7) Uani 1 1 d .
C9 C 0.12968(19) 0.1584(4) 0.3148(2) 0.0713(8) Uani 1 1 d .
H9 H 0.1703 0.1151 0.3720 0.086 Uiso 1 1 calc R
C10 C 0.08002(17) 0.2900(4) 0.31586(17) 0.0623(7) Uani 1 1 d .
C11 C 0.0841(2) 0.3773(4) 0.39759(18) 0.0759(8) Uani 1 1 d .
H11A H 0.1268 0.3168 0.4521 0.091 Uiso 1 1 calc R
H11B H 0.0225 0.3739 0.3952 0.091 Uiso 1 1 calc R
C12 C 0.1158(2) 0.5589(5) 0.4059(2) 0.0858(10) Uani 1 1 d .
H12A H 0.0733 0.6198 0.3515 0.103 Uiso 1 1 calc R
H12B H 0.1777 0.5628 0.4090 0.103 Uiso 1 1 calc R
C13 C 0.1188(3) 0.6454(7) 0.4902(3) 0.1222(16) Uani 1 1 d .
H13A H 0.0571 0.6462 0.4863 0.183 Uiso 1 1 calc R
H13B H 0.1404 0.7589 0.4932 0.183 Uiso 1 1 calc R
H13C H 0.1608 0.5857 0.5443 0.183 Uiso 1 1 calc R
C14 C -0.14118(16) 0.6298(3) 0.16797(16) 0.0543(6) Uani 1 1 d .
C15 C -0.1174(3) 0.7911(4) 0.1566(2) 0.0789(8) Uani 1 1 d .
H15 H -0.1103 0.8190 0.1050 0.095 Uiso 1 1 calc R
C16 C -0.1041(2) 0.9116(4) 0.2222(2) 0.0849(9) Uani 1 1 d .
H16 H -0.0863 1.0197 0.2149 0.102 Uiso 1 1 calc R
C17 C -0.11661(19) 0.8749(4) 0.2979(2) 0.0724(8) Uani 1 1 d .
C18 C -0.1420(2) 0.7146(4) 0.3069(2) 0.0785(9) Uani 1 1 d .
H18 H -0.1513 0.6881 0.3575 0.094 Uiso 1 1 calc R
C19 C -0.1543(2) 0.5905(4) 0.24336(19) 0.0694(7) Uani 1 1 d .
H19 H -0.1711 0.4821 0.2513 0.083 Uiso 1 1 calc R
C20 C -0.1003(3) 1.0087(6) 0.3692(3) 0.1076(13) Uani 1 1 d .
H20A H -0.0349 1.0368 0.4000 0.161 Uiso 1 1 calc R
H20B H -0.1197 0.9671 0.4131 0.161 Uiso 1 1 calc R
H20C H -0.1361 1.1072 0.3399 0.161 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
C1 N1 S1 121.60(18)
C1 O3 C10 124.6(2)
O2 S1 O1 118.18(15)
O2 S1 N1 103.63(14)
O1 S1 N1 110.56(13)
O2 S1 C14 107.69(14)
O1 S1 C14 109.39(14)
N1 S1 C14 106.72(11)
N1 C1 O3 121.4(2)
N1 C1 C2 120.0(2)
O3 C1 C2 118.6(2)
C1 C2 C3 109.6(2)
C1 C2 H2A 109.8
C3 C2 H2A 109.8
C1 C2 H2B 109.8
C3 C2 H2B 109.8
H2A C2 H2B 108.2
C4 C3 C8 120.7(3)
C4 C3 C2 120.6(3)
C8 C3 C2 118.7(2)
C3 C4 C5 119.4(4)
C3 C4 H4 120.3
C5 C4 H4 120.3
C6 C5 C4 121.1(4)
C6 C5 H5 119.4
C4 C5 H5 119.4
C5 C6 C7 120.6(4)
C5 C6 H6 119.7
C7 C6 H6 119.7
C6 C7 C8 120.0(4)
C6 C7 H7 120.0
C8 C7 H7 120.0
C3 C8 C7 118.1(3)
C3 C8 C9 121.2(2)
C7 C8 C9 120.7(3)
C10 C9 C8 128.9(2)
C10 C9 H9 115.6
C8 C9 H9 115.6
C9 C10 O3 122.9(2)
C9 C10 C11 127.1(3)
O3 C10 C11 109.8(2)
C10 C11 C12 113.8(2)
C10 C11 H11A 108.8
C12 C11 H11A 108.8
C10 C11 H11B 108.8
C12 C11 H11B 108.8
H11A C11 H11B 107.7
C11 C12 C13 112.6(3)
C11 C12 H12A 109.1
C13 C12 H12A 109.1
C11 C12 H12B 109.1
C13 C12 H12B 109.1
H12A C12 H12B 107.8
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C15 C14 C19 119.8(2)
C15 C14 S1 119.0(2)
C19 C14 S1 121.2(2)
C14 C15 C16 119.8(3)
C14 C15 H15 120.1
C16 C15 H15 120.1
C17 C16 C15 121.3(3)
C17 C16 H16 119.3
C15 C16 H16 119.3
C18 C17 C16 117.9(3)
C18 C17 C20 122.0(3)
C16 C17 C20 120.2(3)
C17 C18 C19 122.2(3)
C17 C18 H18 118.9
C19 C18 H18 118.9
C14 C19 C18 119.0(3)
C14 C19 H19 120.5
C18 C19 H19 120.5
C17 C20 H20A 109.5
C17 C20 H20B 109.5
H20A C20 H20B 109.5
C17 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.283(3)
N1 S1 1.649(3)
O1 S1 1.431(2)
O2 S1 1.430(2)
O3 C1 1.338(3)
O3 C10 1.418(3)
S1 C14 1.763(3)
C1 C2 1.488(4)
C2 C3 1.498(4)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.383(4)
C3 C8 1.405(4)
C4 C5 1.384(6)
C4 H4 0.9300
C5 C6 1.355(7)
C5 H5 0.9300
C6 C7 1.385(7)
C6 H6 0.9300
C7 C8 1.408(4)
C7 H7 0.9300
C8 C9 1.450(4)
C9 C10 1.319(4)
C9 H9 0.9300
C10 C11 1.482(4)
C11 C12 1.516(5)
C11 H11A 0.9700
C11 H11B 0.9700
C12 C13 1.523(5)
C12 H12A 0.9700
C12 H12B 0.9700
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 C15 1.374(4)
C14 C19 1.378(4)
C15 C16 1.381(4)
C15 H15 0.9300
C16 C17 1.374(5)
C16 H16 0.9300
C17 C18 1.366(5)
C17 C20 1.512(4)
C18 C19 1.382(4)
C18 H18 0.9300
C19 H19 0.9300
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
