#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/63/7106377.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_7106377
loop_
_publ_author_name
'Zhiyuan Chen'
'Chao Ye'
'Liang Gao'
'Jie Wu'
_publ_section_title
;
 Diversity-oriented approach to 1,2-dihydroisoquinolin-3(4H)-imines via
 copper(I)-catalyzed reaction of (E)-2-ethynylphenylchalcone, sulfonyl
 azide and amine
;
_journal_name_full               Chem.Commun.
_journal_page_first              5623
_journal_paper_doi               10.1039/c1cc11176k
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C32.5 H32 N2 O5.5 S'
_chemical_formula_weight         570.66
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 99.370(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.277(10)
_cell_length_b                   10.347(4)
_cell_length_c                   23.279(10)
_cell_measurement_reflns_used    963
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.412
_cell_measurement_theta_min      2.144
_cell_volume                     5770(4)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11615
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_correction_T_min  0.9781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2408
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.805
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         5070
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0593
_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)+(0.1225P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1773
_refine_ls_wR_factor_ref         0.1974
_reflns_number_gt                3258
_reflns_number_total             5070
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc11176k.txt
_cod_data_source_block           a01228c
_cod_original_cell_volume        5769(4)
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C32.50 H32 N2 O5.50 S'
_cod_database_code               7106377
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.80977(3) 0.36527(7) 0.61128(3) 0.0513(3) Uani 1 1 d . . .
N1 N 0.77462(10) 0.2426(2) 0.62730(11) 0.0529(7) Uani 1 1 d . . .
N2 N 0.76483(10) 0.0424(2) 0.66260(10) 0.0459(6) Uani 1 1 d . . .
O1 O 0.83313(10) 0.4380(2) 0.66199(10) 0.0651(6) Uani 1 1 d . . .
O2 O 0.84814(10) 0.3313(2) 0.57283(11) 0.0693(7) Uani 1 1 d . . .
O4 O 0.76956(10) 0.1575(2) 0.78130(10) 0.0711(7) Uani 1 1 d . . .
C1 C 0.75532(13) 0.4562(3) 0.57168(13) 0.0489(8) Uani 1 1 d . . .
C2 C 0.75534(16) 0.5884(3) 0.57749(15) 0.0647(9) Uani 1 1 d . . .
H2 H 0.7832 0.6290 0.6034 0.078 Uiso 1 1 calc R . .
C3 C 0.71412(18) 0.6600(4) 0.54496(16) 0.0772(11) Uani 1 1 d . . .
H3 H 0.7143 0.7492 0.5496 0.093 Uiso 1 1 calc R . .
C4 C 0.67260(16) 0.6041(4) 0.50566(15) 0.0653(9) Uani 1 1 d . . .
C5 C 0.67422(15) 0.4713(4) 0.49959(16) 0.0671(9) Uani 1 1 d . . .
H5 H 0.6473 0.4312 0.4725 0.081 Uiso 1 1 calc R . .
C6 C 0.71429(14) 0.3973(3) 0.53222(15) 0.0597(9) Uani 1 1 d . . .
H6 H 0.7139 0.3079 0.5279 0.072 Uiso 1 1 calc R . .
C7 C 0.62742(18) 0.6842(5) 0.47102(19) 0.0947(14) Uani 1 1 d . . .
H7A H 0.6174 0.7533 0.4948 0.142 Uiso 1 1 calc R . .
H7B H 0.5953 0.6310 0.4584 0.142 Uiso 1 1 calc R . .
H7C H 0.6407 0.7195 0.4377 0.142 Uiso 1 1 calc R . .
C8 C 0.70687(12) 0.0466(3) 0.63700(13) 0.0467(7) Uani 1 1 d . . .
C9 C 0.69197(14) 0.0259(3) 0.57824(14) 0.0555(8) Uani 1 1 d . . .
H9 H 0.7194 0.0100 0.5555 0.067 Uiso 1 1 calc R . .
C10 C 0.63694(14) 0.0284(4) 0.55283(14) 0.0622(9) Uani 1 1 d . . .
H10 H 0.6273 0.0168 0.5128 0.075 Uiso 1 1 calc R . .
C11 C 0.59596(13) 0.0482(3) 0.58643(15) 0.0566(8) Uani 1 1 d . . .
C12 C 0.61001(14) 0.0708(3) 0.64471(15) 0.0629(9) Uani 1 1 d . . .
H12 H 0.5825 0.0866 0.6673 0.075 Uiso 1 1 calc R . .
C13 C 0.66579(14) 0.0700(3) 0.66984(14) 0.0583(8) Uani 1 1 d . . .
H13 H 0.6756 0.0855 0.7095 0.070 Uiso 1 1 calc R . .
C14 C 0.79814(12) 0.1421(3) 0.65510(12) 0.0472(7) Uani 1 1 d . . .
C15 C 0.85891(13) 0.1309(3) 0.67869(15) 0.0564(8) Uani 1 1 d . . .
H15A H 0.8660 0.1724 0.7165 0.068 Uiso 1 1 calc R . .
H15B H 0.8798 0.1776 0.6532 0.068 Uiso 1 1 calc R . .
C16 C 0.88028(13) -0.0053(3) 0.68494(13) 0.0515(8) Uani 1 1 d . . .
C17 C 0.93509(14) -0.0344(4) 0.68270(15) 0.0650(9) Uani 1 1 d . . .
H17 H 0.9598 0.0317 0.6774 0.078 Uiso 1 1 calc R . .
C18 C 0.95404(16) -0.1599(4) 0.68825(17) 0.0737(10) Uani 1 1 d . . .
H18 H 0.9914 -0.1780 0.6875 0.088 Uiso 1 1 calc R . .
C19 C 0.91762(16) -0.2584(4) 0.69499(15) 0.0717(10) Uani 1 1 d . . .
H19 H 0.9302 -0.3434 0.6977 0.086 Uiso 1 1 calc R . .
C20 C 0.86225(14) -0.2310(3) 0.69774(13) 0.0585(8) Uani 1 1 d . . .
H20 H 0.8376 -0.2975 0.7026 0.070 Uiso 1 1 calc R . .
C21 C 0.84362(13) -0.1040(3) 0.69323(12) 0.0489(7) Uani 1 1 d . . .
C22 C 0.78406(13) -0.0733(3) 0.69740(13) 0.0494(7) Uani 1 1 d . . .
H22 H 0.7616 -0.1460 0.6797 0.059 Uiso 1 1 calc R . .
C23 C 0.77420(14) -0.0643(3) 0.76088(14) 0.0566(8) Uani 1 1 d . . .
H23A H 0.7344 -0.0693 0.7616 0.068 Uiso 1 1 calc R . .
H23B H 0.7917 -0.1379 0.7823 0.068 Uiso 1 1 calc R . .
C24 C 0.79666(14) 0.0577(3) 0.79093(14) 0.0563(8) Uani 1 1 d . . .
C25 C 0.85150(14) 0.0615(3) 0.82964(14) 0.0554(8) Uani 1 1 d . . .
C26 C 0.88148(17) -0.0475(4) 0.85039(17) 0.0724(10) Uani 1 1 d . . .
H26 H 0.8673 -0.1290 0.8395 0.087 Uiso 1 1 calc R . .
C27 C 0.93153(19) -0.0368(4) 0.88653(19) 0.0871(13) Uani 1 1 d . . .
H27 H 0.9509 -0.1114 0.9000 0.105 Uiso 1 1 calc R . .
C28 C 0.95400(16) 0.0824(4) 0.90350(17) 0.0734(11) Uani 1 1 d . . .
C29 C 0.92485(16) 0.1916(4) 0.88327(18) 0.0778(11) Uani 1 1 d . . .
H29 H 0.9393 0.2730 0.8939 0.093 Uiso 1 1 calc R . .
C30 C 0.87447(15) 0.1801(4) 0.84741(17) 0.0700(10) Uani 1 1 d . . .
H30 H 0.8550 0.2548 0.8345 0.084 Uiso 1 1 calc R . .
C31 C 1.02794(19) 0.2032(6) 0.9605(2) 0.1225(19) Uani 1 1 d . . .
H31A H 1.0387 0.2516 0.9289 0.184 Uiso 1 1 calc R . .
H31B H 1.0602 0.1876 0.9895 0.184 Uiso 1 1 calc R . .
H31C H 1.0009 0.2514 0.9775 0.184 Uiso 1 1 calc R . .
O3 O 0.54229(10) 0.0447(3) 0.55650(12) 0.0800(8) Uani 1 1 d . . .
C32 C 0.49787(16) 0.0697(5) 0.5877(2) 0.0933(14) Uani 1 1 d . . .
H32A H 0.5011 0.1561 0.6029 0.140 Uiso 1 1 calc R . .
H32B H 0.4995 0.0094 0.6193 0.140 Uiso 1 1 calc R . .
H32C H 0.4629 0.0604 0.5621 0.140 Uiso 1 1 calc R . .
O5 O 1.00420(13) 0.0820(3) 0.93907(14) 0.1010(10) Uani 1 1 d . . .
C34 C 0.5449(4) 0.8892(13) 0.8172(4) 0.144(5) Uani 0.50 1 d PD . .
O7 O 0.5303(3) 0.8573(11) 0.7575(4) 0.175(4) Uani 0.50 1 d PD . .
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
O1 S1 O2 115.53(15) . . ?
O1 S1 N1 112.13(14) . . ?
O2 S1 N1 111.96(14) . . ?
O1 S1 C1 108.26(14) . . ?
O2 S1 C1 108.24(15) . . ?
N1 S1 C1 99.32(14) . . ?
C14 N1 S1 122.5(2) . . ?
C14 N2 C8 119.6(2) . . ?
C14 N2 C22 123.5(3) . . ?
C8 N2 C22 116.9(2) . . ?
C2 C1 C6 119.5(3) . . ?
C2 C1 S1 119.5(3) . . ?
C6 C1 S1 120.8(2) . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 122.1(3) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 117.1(3) . . ?
C3 C4 C7 121.2(4) . . ?
C5 C4 C7 121.6(4) . . ?
C6 C5 C4 122.0(3) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 119.0(3) . . ?
C13 C8 N2 121.7(3) . . ?
C9 C8 N2 119.3(3) . . ?
C10 C9 C8 120.5(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.1(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 O3 124.9(3) . . ?
C12 C11 C10 120.2(3) . . ?
O3 C11 C10 114.9(3) . . ?
C11 C12 C13 119.2(3) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C8 C13 C12 121.0(3) . . ?
C8 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
N1 C14 N2 116.9(3) . . ?
N1 C14 C15 124.8(3) . . ?
N2 C14 C15 118.3(3) . . ?
C14 C15 C16 114.4(3) . . ?
C14 C15 H15A 108.6 . . ?
C16 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
C16 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C17 C16 C21 119.4(3) . . ?
C17 C16 C15 121.6(3) . . ?
C21 C16 C15 119.0(3) . . ?
C16 C17 C18 120.9(3) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.0(3) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C21 119.8(3) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C16 119.9(3) . . ?
C20 C21 C22 120.1(3) . . ?
C16 C21 C22 120.0(3) . . ?
N2 C22 C21 111.0(2) . . ?
N2 C22 C23 113.2(2) . . ?
C21 C22 C23 112.2(3) . . ?
N2 C22 H22 106.7 . . ?
C21 C22 H22 106.7 . . ?
C23 C22 H22 106.7 . . ?
C24 C23 C22 113.4(3) . . ?
C24 C23 H23A 108.9 . . ?
C22 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
C22 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
O4 C24 C25 119.4(3) . . ?
O4 C24 C23 118.7(3) . . ?
C25 C24 C23 121.9(3) . . ?
C30 C25 C26 117.0(3) . . ?
C30 C25 C24 119.0(3) . . ?
C26 C25 C24 124.0(3) . . ?
C27 C26 C25 120.9(4) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C26 C27 C28 121.3(4) . . ?
C26 C27 H27 119.4 . . ?
C28 C27 H27 119.4 . . ?
O5 C28 C29 124.9(4) . . ?
O5 C28 C27 116.5(4) . . ?
C29 C28 C27 118.6(4) . . ?
C30 C29 C28 119.7(4) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C29 C30 C25 122.4(3) . . ?
C29 C30 H30 118.8 . . ?
C25 C30 H30 118.8 . . ?
O5 C31 H31A 109.5 . . ?
O5 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O5 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C11 O3 C32 118.2(3) . . ?
O3 C32 H32A 109.5 . . ?
O3 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O3 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C28 O5 C31 118.7(4) . . ?
C34 O7 O7 108.6(10) . 2_656 ?
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 O1 1.437(2) . ?
S1 O2 1.437(2) . ?
S1 N1 1.607(3) . ?
S1 C1 1.756(3) . ?
N1 C14 1.306(4) . ?
N2 C14 1.340(4) . ?
N2 C8 1.437(4) . ?
N2 C22 1.478(4) . ?
O4 C24 1.226(4) . ?
C1 C2 1.374(4) . ?
C1 C6 1.382(4) . ?
C2 C3 1.370(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(5) . ?
C4 C7 1.501(5) . ?
C5 C6 1.368(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C13 1.373(4) . ?
C8 C9 1.374(4) . ?
C9 C10 1.370(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.364(5) . ?
C11 O3 1.374(4) . ?
C12 C13 1.385(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.492(4) . ?
C15 C16 1.501(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.373(4) . ?
C16 C21 1.389(4) . ?
C17 C18 1.377(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.385(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.388(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.499(4) . ?
C22 C23 1.538(5) . ?
C22 H22 0.9800 . ?
C23 C24 1.502(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.482(5) . ?
C25 C30 1.383(5) . ?
C25 C26 1.386(5) . ?
C26 C27 1.365(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.380(6) . ?
C27 H27 0.9300 . ?
C28 O5 1.357(5) . ?
C28 C29 1.376(5) . ?
C29 C30 1.369(5) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 O5 1.435(6) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
O3 C32 1.419(5) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C34 O7 1.415(2) . ?
