#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:01:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178456 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/77/4027726.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_4027726
loop_
_publ_author_name
'Luping Liu'
'Yuan Zhong'
'Panpan Zhang'
'Xianxing Jiang'
'Rui Wang'
_publ_section_title
;
 Core Scaffold-Inspired Stereoselective Synthesis of Spiropyrazolones via
 an Organocatalytic Michael/Cyclization Sequence
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10228
_journal_page_last               10234
_journal_paper_doi               10.1021/jo301851a
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C23 H20 N4 O4 S'
_chemical_formula_weight         448.49
_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                 106.582(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.07(2)
_cell_length_b                   11.657(17)
_cell_length_c                   15.58(2)
_cell_measurement_reflns_used    1045
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.62
_cell_measurement_theta_min      2.22
_cell_volume                     2449(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.1016
_diffrn_reflns_av_sigmaI/netI    0.1292
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12991
_diffrn_reflns_theta_full        24.92
_diffrn_reflns_theta_max         24.92
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.9691
_exptl_absorpt_correction_T_min  0.9628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_platon_squeeze_details          ' '
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         4251
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1826
_refine_ls_R_factor_gt           0.0891
_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)+(0.0822P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1945
_refine_ls_wR_factor_ref         0.2244
_reflns_number_gt                1908
_reflns_number_total             4251
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301851a_si_002.cif
_cod_data_source_block           p21c
_cod_original_cell_volume        2448(6)
_cod_database_code               4027726
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
C18 C 0.8394(3) 1.0842(4) -0.0666(2) 0.0504(15) Uani 1 1 d G
C19 C 0.7782(3) 1.0790(5) -0.1540(3) 0.117(3) Uani 1 1 d G
H19 H 0.7127 1.0553 -0.1652 0.141 Uiso 1 1 calc R
C20 C 0.8150(4) 1.1092(5) -0.2248(2) 0.144(4) Uani 1 1 d G
H20 H 0.7740 1.1057 -0.2833 0.173 Uiso 1 1 calc R
C21 C 0.9129(4) 1.1446(4) -0.2081(3) 0.084(2) Uani 1 1 d G
H21 H 0.9375 1.1649 -0.2555 0.101 Uiso 1 1 calc R
C22 C 0.9741(3) 1.1499(5) -0.1206(4) 0.102(3) Uani 1 1 d G
H22 H 1.0396 1.1736 -0.1095 0.122 Uiso 1 1 calc R
C23 C 0.9373(3) 1.1197(5) -0.0499(3) 0.095(3) Uani 1 1 d G
H23 H 0.9783 1.1232 0.0087 0.114 Uiso 1 1 calc R
C1 C 0.5944(5) 0.5970(5) 0.0817(4) 0.0501(15) Uani 1 1 d .
C2 C 0.5321(6) 0.4648(5) 0.1606(4) 0.074(2) Uani 1 1 d .
H2A H 0.5682 0.4145 0.2084 0.089 Uiso 1 1 calc R
H2B H 0.4685 0.4302 0.1310 0.089 Uiso 1 1 calc R
C3 C 0.5184(5) 0.5801(5) 0.1965(4) 0.070(2) Uani 1 1 d .
H3A H 0.4495 0.5937 0.1933 0.084 Uiso 1 1 calc R
H3B H 0.5589 0.5889 0.2579 0.084 Uiso 1 1 calc R
C4 C 0.5360(4) 0.7712(5) 0.1397(4) 0.0459(15) Uani 1 1 d .
C5 C 0.5859(4) 0.8514(4) 0.0875(3) 0.0414(14) Uani 1 1 d .
H5 H 0.5624 0.8325 0.0236 0.050 Uiso 1 1 calc R
C6 C 0.6983(4) 0.8544(4) 0.1163(3) 0.0408(14) Uani 1 1 d .
H6 H 0.7225 0.8068 0.0751 0.049 Uiso 1 1 calc R
C7 C 0.7195(4) 0.9835(4) 0.1001(3) 0.0393(13) Uani 1 1 d .
C8 C 0.6278(4) 1.0442(5) 0.1103(3) 0.0428(14) Uani 1 1 d .
C9 C 0.7477(4) 0.8152(4) 0.2111(4) 0.0433(14) Uani 1 1 d .
C10 C 0.7158(4) 0.8532(5) 0.2821(4) 0.0538(16) Uani 1 1 d .
H10 H 0.6636 0.9052 0.2722 0.065 Uiso 1 1 calc R
C11 C 0.7608(5) 0.8146(7) 0.3680(4) 0.079(2) Uani 1 1 d .
H11 H 0.7387 0.8396 0.4157 0.095 Uiso 1 1 calc R
C12 C 0.8375(6) 0.7401(8) 0.3821(5) 0.098(3) Uani 1 1 d .
H12 H 0.8697 0.7162 0.4401 0.117 Uiso 1 1 calc R
C13 C 0.8680(6) 0.6999(7) 0.3129(5) 0.100(3) Uani 1 1 d .
H13 H 0.9189 0.6463 0.3231 0.120 Uiso 1 1 calc R
C14 C 0.8236(5) 0.7383(5) 0.2278(4) 0.0682(19) Uani 1 1 d .
H14 H 0.8457 0.7114 0.1807 0.082 Uiso 1 1 calc R
C15 C 0.8184(4) 1.0367(5) 0.1457(4) 0.0516(16) Uani 1 1 d .
C16 C 0.7176(4) 0.9990(4) 0.0020(4) 0.0384(13) Uani 1 1 d .
C17 C 0.8615(5) 1.0532(5) 0.2440(4) 0.073(2) Uani 1 1 d .
H17A H 0.8804 0.9801 0.2721 0.109 Uiso 1 1 calc R
H17B H 0.8131 1.0883 0.2683 0.109 Uiso 1 1 calc R
H17C H 0.9188 1.1017 0.2549 0.109 Uiso 1 1 calc R
N1 N 0.5513(3) 0.6563(3) 0.1364(3) 0.0444(12) Uani 1 1 d .
N2 N 0.5579(3) 0.9676(4) 0.1006(3) 0.0436(12) Uani 1 1 d .
H2 H 0.4989 0.9853 0.1018 0.052 Uiso 1 1 calc R
N3 N 0.8634(3) 1.0752(4) 0.0921(3) 0.0501(13) Uani 1 1 d .
N4 N 0.8049(3) 1.0517(4) 0.0044(3) 0.0469(12) Uani 1 1 d .
O1 O 0.6329(3) 0.6349(3) 0.0277(3) 0.0636(13) Uani 1 1 d .
O2 O 0.5885(3) 0.4854(3) 0.0973(3) 0.0729(13) Uani 1 1 d .
O3 O 0.4873(3) 0.8093(3) 0.1847(3) 0.0641(12) Uani 1 1 d .
O4 O 0.6521(3) 0.9713(3) -0.0630(2) 0.0483(10) Uani 1 1 d .
S1 S 0.62018(13) 1.18281(13) 0.12405(12) 0.0646(6) Uani 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
N4 C18 C19 120.8(4)
N4 C18 C23 119.2(4)
C19 C18 C23 120.0
C18 C19 C20 120.0
C18 C19 H19 120.0
C20 C19 H19 120.0
C21 C20 C19 120.0
C21 C20 H20 120.0
C19 C20 H20 120.0
C20 C21 C22 120.0
C20 C21 H21 120.0
C22 C21 H21 120.0
C21 C22 C23 120.0
C21 C22 H22 120.0
C23 C22 H22 120.0
C22 C23 C18 120.0
C22 C23 H23 120.0
C18 C23 H23 120.0
O1 C1 O2 123.3(5)
O1 C1 N1 128.1(5)
O2 C1 N1 108.6(5)
O2 C2 C3 105.1(5)
O2 C2 H2A 110.7
C3 C2 H2A 110.7
O2 C2 H2B 110.7
C3 C2 H2B 110.7
H2A C2 H2B 108.8
N1 C3 C2 102.2(5)
N1 C3 H3A 111.3
C2 C3 H3A 111.3
N1 C3 H3B 111.3
C2 C3 H3B 111.3
H3A C3 H3B 109.2
O3 C4 N1 120.8(5)
O3 C4 C5 120.6(5)
N1 C4 C5 118.6(5)
N2 C5 C6 103.9(4)
N2 C5 C4 108.2(4)
C6 C5 C4 117.0(4)
N2 C5 H5 109.1
C6 C5 H5 109.1
C4 C5 H5 109.1
C9 C6 C5 115.6(4)
C9 C6 C7 113.1(4)
C5 C6 C7 101.8(4)
C9 C6 H6 108.7
C5 C6 H6 108.7
C7 C6 H6 108.7
C15 C7 C8 117.2(5)
C15 C7 C16 100.0(4)
C8 C7 C16 106.0(4)
C15 C7 C6 120.8(4)
C8 C7 C6 103.0(4)
C16 C7 C6 108.9(4)
N2 C8 C7 107.7(5)
N2 C8 S1 127.9(5)
C7 C8 S1 124.3(4)
C14 C9 C10 118.3(6)
C14 C9 C6 120.2(5)
C10 C9 C6 121.5(5)
C9 C10 C11 120.5(6)
C9 C10 H10 119.8
C11 C10 H10 119.8
C12 C11 C10 119.4(7)
C12 C11 H11 120.3
C10 C11 H11 120.3
C13 C12 C11 120.8(7)
C13 C12 H12 119.6
C11 C12 H12 119.6
C12 C13 C14 119.8(7)
C12 C13 H13 120.1
C14 C13 H13 120.1
C9 C14 C13 121.1(6)
C9 C14 H14 119.4
C13 C14 H14 119.4
N3 C15 C17 119.9(5)
N3 C15 C7 113.9(5)
C17 C15 C7 126.1(5)
O4 C16 N4 127.7(5)
O4 C16 C7 126.9(5)
N4 C16 C7 105.4(5)
C15 C17 H17A 109.5
C15 C17 H17B 109.5
H17A C17 H17B 109.5
C15 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C4 N1 C1 128.7(5)
C4 N1 C3 119.5(5)
C1 N1 C3 111.8(5)
C8 N2 C5 115.6(5)
C8 N2 H2 122.2
C5 N2 H2 122.2
C15 N3 N4 107.9(5)
C16 N4 C18 128.4(5)
C16 N4 N3 112.8(4)
C18 N4 N3 118.8(4)
C1 O2 C2 111.1(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C18 N4 1.382(5)
C18 C19 1.3900
C18 C23 1.3900
C19 C20 1.3900
C19 H19 0.9300
C20 C21 1.3900
C20 H20 0.9300
C21 C22 1.3900
C21 H21 0.9300
C22 C23 1.3900
C22 H22 0.9300
C23 H23 0.9300
C1 O1 1.207(6)
C1 O2 1.330(7)
C1 N1 1.366(7)
C2 O2 1.452(7)
C2 C3 1.488(8)
C2 H2A 0.9700
C2 H2B 0.9700
C3 N1 1.458(6)
C3 H3A 0.9700
C3 H3B 0.9700
C4 O3 1.195(6)
C4 N1 1.360(7)
C4 C5 1.535(7)
C5 N2 1.442(6)
C5 C6 1.516(8)
C5 H5 0.9800
C6 C9 1.511(7)
C6 C7 1.569(7)
C6 H6 0.9800
C7 C15 1.504(7)
C7 C8 1.519(7)
C7 C16 1.531(7)
C8 N2 1.305(6)
C8 S1 1.637(6)
C9 C14 1.361(8)
C9 C10 1.381(7)
C10 C11 1.382(8)
C10 H10 0.9300
C11 C12 1.353(9)
C11 H11 0.9300
C12 C13 1.352(10)
C12 H12 0.9300
C13 C14 1.370(9)
C13 H13 0.9300
C14 H14 0.9300
C15 N3 1.265(7)
C15 C17 1.489(8)
C16 O4 1.202(6)
C16 N4 1.364(7)
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
N2 H2 0.8600
N3 N4 1.407(6)
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
N4 C18 C19 C20 -178.3(4)
C23 C18 C19 C20 0.0
C18 C19 C20 C21 0.0
C19 C20 C21 C22 0.0
C20 C21 C22 C23 0.0
C21 C22 C23 C18 0.0
N4 C18 C23 C22 178.4(4)
C19 C18 C23 C22 0.0
O2 C2 C3 N1 10.9(7)
O3 C4 C5 N2 -3.0(7)
N1 C4 C5 N2 179.4(5)
O3 C4 C5 C6 113.9(6)
N1 C4 C5 C6 -63.7(7)
N2 C5 C6 C9 97.2(5)
C4 C5 C6 C9 -22.0(6)
N2 C5 C6 C7 -25.7(5)
C4 C5 C6 C7 -144.9(4)
C9 C6 C7 C15 35.6(7)
C5 C6 C7 C15 160.2(5)
C9 C6 C7 C8 -97.5(5)
C5 C6 C7 C8 27.1(5)
C9 C6 C7 C16 150.3(4)
C5 C6 C7 C16 -85.1(5)
C15 C7 C8 N2 -154.3(5)
C16 C7 C8 N2 95.2(5)
C6 C7 C8 N2 -19.1(5)
C15 C7 C8 S1 29.5(6)
C16 C7 C8 S1 -81.0(5)
C6 C7 C8 S1 164.7(4)
C5 C6 C9 C14 131.8(6)
C7 C6 C9 C14 -111.4(6)
C5 C6 C9 C10 -46.4(7)
C7 C6 C9 C10 70.4(7)
C14 C9 C10 C11 0.6(9)
C6 C9 C10 C11 178.8(6)
C9 C10 C11 C12 0.8(11)
C10 C11 C12 C13 -2.5(13)
C11 C12 C13 C14 2.7(14)
C10 C9 C14 C13 -0.4(10)
C6 C9 C14 C13 -178.7(6)
C12 C13 C14 C9 -1.2(12)
C8 C7 C15 N3 -113.1(5)
C16 C7 C15 N3 0.8(6)
C6 C7 C15 N3 120.0(5)
C8 C7 C15 C17 62.8(7)
C16 C7 C15 C17 176.7(5)
C6 C7 C15 C17 -64.1(8)
C15 C7 C16 O4 -179.0(5)
C8 C7 C16 O4 -56.8(7)
C6 C7 C16 O4 53.4(7)
C15 C7 C16 N4 0.3(5)
C8 C7 C16 N4 122.5(5)
C6 C7 C16 N4 -127.3(5)
O3 C4 N1 C1 171.6(5)
C5 C4 N1 C1 -10.8(9)
O3 C4 N1 C3 -7.4(9)
C5 C4 N1 C3 170.1(5)
O1 C1 N1 C4 4.4(11)
O2 C1 N1 C4 -176.0(6)
O1 C1 N1 C3 -176.5(6)
O2 C1 N1 C3 3.1(7)
C2 C3 N1 C4 170.2(6)
C2 C3 N1 C1 -9.0(7)
C7 C8 N2 C5 2.6(6)
S1 C8 N2 C5 178.5(4)
C6 C5 N2 C8 15.8(6)
C4 C5 N2 C8 140.8(5)
C17 C15 N3 N4 -177.8(5)
C7 C15 N3 N4 -1.6(6)
O4 C16 N4 C18 -1.1(9)
C7 C16 N4 C18 179.7(5)
O4 C16 N4 N3 178.0(5)
C7 C16 N4 N3 -1.3(6)
C19 C18 N4 C16 9.0(7)
C23 C18 N4 C16 -169.4(5)
C19 C18 N4 N3 -170.1(4)
C23 C18 N4 N3 11.6(6)
C15 N3 N4 C16 1.8(6)
C15 N3 N4 C18 -179.0(5)
O1 C1 O2 C2 -175.8(6)
N1 C1 O2 C2 4.6(7)
C3 C2 O2 C1 -10.2(7)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.500 246 90 ' '
2 1.000 0.500 1.000 246 90 ' '
