#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/71/4027195.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_4027195
loop_
_publ_author_name
'Masatoshi, Tanimura'
'Nobuko Watanabe'
'Hisako K. Ijuin'
'Masakatsu Matsumoto'
_publ_contact_author_email       matsumo-chem@kanagawa-u.ac.jp
_publ_contact_author_fax         81(463)589684
_publ_contact_author_name        'Professor Masakatsu Matsumoto'
_publ_contact_author_phone       81(463)594111
_publ_section_title
;
 Base-Induced Chemiluminescent Decomposition of Bicyclic Dioxetanes
 Bearing a (Benzothiazol-2-yl)-3-hydroxyphenyl Group: A Radiationless
 Pathway Leading to Marked Decline of Chemiluminescence Efficiency
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4725
_journal_page_last               4731
_journal_paper_doi               10.1021/jo300417e
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C23 H25 N O4 S '
_chemical_formula_sum            'C23 H25 N O4 S'
_chemical_formula_weight         411.51
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_audit_creation_date             2010-03-23
_audit_creation_method           'by CrystalStructure 3.6.0'
_cell_angle_alpha                90
_cell_angle_beta                 94.278(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.143(3)
_cell_length_b                   12.249(3)
_cell_length_c                   15.112(4)
_cell_measurement_reflns_used    8439
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.2
_cell_volume                     2056.9(9)
_computing_cell_refinement       DTREK
_computing_data_collection       DTREK
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.6.0'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.9883
_diffrn_measured_fraction_theta_max 0.9883
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22245
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  0.911
_exptl_absorpt_correction_T_min  0.831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       block
_exptl_crystal_F_000             872.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.40
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     287
_refine_ls_number_reflns         3416
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[0.0010Fo² + 1.0000σ(Fo²)]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0550
_reflns_number_gt                3416
_reflns_number_total             4659
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo300417e_si_002.cif
_cod_data_source_block           '__1c'
_cod_original_cell_volume        2057.0(9)
_cod_original_formula_sum        'C23 H25 N O4 S '
_cod_database_code               4027195
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,+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
S(1) S 0.88876(5) 0.24188(4) 0.59502(4) 0.0503(2) Uani 1.00 1 d .
O(2) O 0.78494(10) 0.05553(10) 0.96003(8) 0.0302(3) Uani 1.00 1 d .
O(3) O 0.89646(11) 0.10997(10) 0.93258(8) 0.0314(3) Uani 1.00 1 d .
O(1) O 1.27019(11) -0.05806(11) 0.85789(9) 0.0383(4) Uani 1.00 1 d .
O(4) O 0.81905(11) 0.18658(10) 0.79691(8) 0.0328(3) Uani 1.00 1 d .
N(2) N 0.80136(13) 0.04680(12) 0.59536(10) 0.0302(4) Uani 1.00 1 d .
C(13) C 0.9704(2) 0.05387(13) 0.79115(11) 0.0262(4) Uani 1.00 1 d .
C(15) C 0.7478(2) 0.0255(1) 0.86676(11) 0.0259(4) Uani 1.00 1 d .
C(14) C 0.8612(2) 0.09150(13) 0.83812(11) 0.0264(4) Uani 1.00 1 d .
C(16) C 0.6390(2) 0.1012(2) 0.83789(12) 0.0305(5) Uani 1.00 1 d .
C(11) C 1.1739(2) -0.0180(2) 0.80697(12) 0.0304(5) Uani 1.00 1 d .
C(20) C 0.7405(2) -0.1010(1) 0.85948(12) 0.0286(4) Uani 1.00 1 d .
C(7) C 0.8845(2) 0.1077(1) 0.63382(11) 0.0290(4) Uani 1.00 1 d .
C(8) C 0.9811(2) 0.0658(1) 0.69898(11) 0.0291(4) Uani 1.00 1 d .
C(9) C 1.0878(2) 0.0340(2) 0.66365(13) 0.0403(5) Uani 1.00 1 d .
C(6) C 0.7309(2) 0.1061(1) 0.53240(11) 0.0282(4) Uani 1.00 1 d .
C(5) C 0.6324(2) 0.0648(2) 0.48054(13) 0.0379(5) Uani 1.00 1 d .
C(18) C 0.5746(2) 0.0721(2) 0.74788(13) 0.0420(6) Uani 1.00 1 d .
C(12) C 1.0679(2) 0.0127(1) 0.84384(12) 0.0279(4) Uani 1.00 1 d .
C(3) C 0.6027(2) 0.2422(2) 0.41312(13) 0.0427(6) Uani 1.00 1 d .
C(21) C 0.8497(2) -0.1542(2) 0.9106(1) 0.0412(6) Uani 1.00 1 d .
C(1) C 0.7646(2) 0.2151(2) 0.52258(12) 0.0360(5) Uani 1.00 1 d .
C(23) C 0.7394(2) -0.1400(2) 0.76303(13) 0.0418(6) Uani 1.00 1 d .
C(19) C 0.5455(2) 0.1121(2) 0.90722(13) 0.0379(5) Uani 1.00 1 d .
C(10) C 1.1841(2) -0.0079(2) 0.71626(13) 0.0411(6) Uani 1.00 1 d .
C(17) C 0.7040(2) 0.2112(2) 0.83041(13) 0.0352(5) Uani 1.00 1 d .
C(22) C 0.6280(2) -0.1427(2) 0.9024(2) 0.0451(6) Uani 1.00 1 d .
C(4) C 0.5687(2) 0.1333(2) 0.42167(13) 0.0400(5) Uani 1.00 1 d .
C(2) C 0.7003(2) 0.2837(2) 0.4623(1) 0.0469(6) Uani 1.00 1 d .
H(1) H 0.7248 0.3595 0.4563 0.056 Uiso 1.00 1 c R
H(2) H 0.5535 0.2925 0.3728 0.051 Uiso 1.00 1 c R
H(3) H 0.4980 0.1050 0.3845 0.047 Uiso 1.00 1 c R
H(4) H 0.6107 -0.0080 0.4877 0.045 Uiso 1.00 1 c R
H(5) H 1.0935 0.0412 0.5979 0.049 Uiso 1.00 1 c R
H(6) H 1.2554 -0.0346 0.6893 0.050 Uiso 1.00 1 c R
H(7) H 1.0626 0.0075 0.9065 0.033 Uiso 1.00 1 c R
H(8) H 1.2550 -0.0586 0.9149 0.046 Uiso 1.00 1 c R
H(9) H 0.7183 0.2473 0.8914 0.042 Uiso 1.00 1 c R
H(10) H 0.6630 0.2595 0.7870 0.042 Uiso 1.00 1 c R
H(11) H 0.4889 0.0490 0.9046 0.046 Uiso 1.00 1 c R
H(12) H 0.5840 0.1219 0.9709 0.046 Uiso 1.00 1 c R
H(13) H 0.4957 0.1797 0.8924 0.046 Uiso 1.00 1 c R
H(14) H 0.5296 -0.0008 0.7505 0.050 Uiso 1.00 1 c R
H(15) H 0.5201 0.1300 0.7310 0.050 Uiso 1.00 1 c R
H(16) H 0.6355 0.0693 0.6993 0.050 Uiso 1.00 1 c R
H(17) H 0.7464 -0.2201 0.7647 0.050 Uiso 1.00 1 c R
H(18) H 0.6643 -0.1228 0.7276 0.051 Uiso 1.00 1 c R
H(19) H 0.8070 -0.1131 0.7295 0.051 Uiso 1.00 1 c R
H(20) H 0.6277 -0.2238 0.9006 0.055 Uiso 1.00 1 c R
H(21) H 0.6295 -0.1148 0.9700 0.055 Uiso 1.00 1 c R
H(22) H 0.5548 -0.1207 0.8687 0.054 Uiso 1.00 1 c R
H(23) H 0.8403 -0.2379 0.9069 0.049 Uiso 1.00 1 c R
H(24) H 0.8623 -0.1305 0.9756 0.049 Uiso 1.00 1 c R
H(25) H 0.9224 -0.1369 0.8814 0.049 Uiso 1.00 1 c R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.125 0.123
;
International Tables for Crystallography
(1992, 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
S(1) C(7) N(2) 115.3(1)
S(1) C(7) C(8) 120.5(1)
C(1) S(1) C(7) 89.66(9)
S(1) C(1) C(6) 108.8(1)
S(1) C(1) C(2) 130.2(2)
C(15) O(2) O(3) 91.5(1)
O(2) O(3) C(14) 91.9(1)
O(2) C(15) C(14) 87.8(1)
O(2) C(15) C(16) 105.8(1)
O(2) C(15) C(20) 108.9(1)
O(3) C(14) O(4) 111.4(1)
O(3) C(14) C(13) 109.5(1)
O(3) C(14) C(15) 88.5(1)
O(1) C(11) C(12) 121.7(2)
O(1) C(11) C(10) 118.0(2)
O(4) C(14) C(13) 107.5(1)
O(4) C(14) C(15) 107.5(1)
C(17) O(4) C(14) 107.3(1)
O(4) C(17) C(16) 106.2(1)
N(2) C(7) C(8) 123.7(2)
C(6) N(2) C(7) 110.8(1)
N(2) C(6) C(1) 115.4(1)
N(2) C(6) C(5) 125.0(2)
C(8) C(13) C(14) 123.8(1)
C(13) C(14) C(15) 130.7(1)
C(12) C(13) C(14) 117.3(1)
C(13) C(8) C(7) 125.1(2)
C(13) C(8) C(9) 119.0(2)
C(12) C(13) C(8) 118.7(2)
C(13) C(12) C(11) 121.1(2)
C(16) C(15) C(14) 103.8(1)
C(20) C(15) C(14) 121.8(1)
C(20) C(15) C(16) 122.5(1)
C(15) C(16) C(19) 114.4(1)
C(15) C(16) C(17) 100.4(1)
C(15) C(16) C(18) 114.3(2)
C(15) C(20) C(21) 110.6(1)
C(15) C(20) C(22) 109.9(1)
C(15) C(20) C(23) 112.0(1)
C(19) C(16) C(18) 109.2(1)
C(17) C(16) C(18) 109.3(2)
C(17) C(16) C(19) 108.7(2)
C(10) C(11) C(12) 120.3(2)
C(11) C(10) C(9) 118.8(2)
C(22) C(20) C(21) 106.6(2)
C(23) C(20) C(21) 107.2(2)
C(22) C(20) C(23) 110.3(2)
C(7) C(8) C(9) 115.9(2)
C(8) C(9) C(10) 122.0(2)
C(1) C(6) C(5) 119.6(2)
C(6) C(5) C(4) 119.1(2)
C(6) C(1) C(2) 121.0(2)
C(5) C(4) C(3) 120.7(2)
C(2) C(3) C(4) 121.0(2)
C(3) C(2) C(1) 118.6(2)
H(8) O(1) C(11) 110.5028
O(4) C(17) H(9) 108.8500
O(4) C(17) H(10) 105.9530
C(13) C(12) H(7) 119.2091
C(16) C(18) H(15) 108.0697
C(16) C(18) H(16) 110.4158
C(16) C(18) H(14) 111.4623
C(16) C(19) H(11) 111.3680
C(16) C(19) H(12) 112.9526
C(16) C(19) H(13) 107.9743
C(16) C(17) H(9) 110.8030
C(16) C(17) H(10) 112.4902
C(11) C(12) H(7) 119.6268
C(11) C(10) H(6) 120.7444
C(20) C(21) H(24) 114.1470
C(20) C(21) H(25) 109.5123
C(20) C(21) H(23) 108.7335
C(20) C(23) H(18) 113.4454
C(20) C(23) H(19) 115.2657
C(20) C(23) H(17) 106.9704
C(20) C(22) H(21) 109.7914
C(20) C(22) H(22) 111.5010
C(20) C(22) H(20) 108.6371
C(8) C(9) H(5) 118.2076
H(5) C(9) C(10) 119.7895
C(9) C(10) H(6) 120.3029
C(6) C(5) H(4) 118.8471
H(4) C(5) C(4) 122.0666
C(5) C(4) H(3) 119.9177
H(15) C(18) H(14) 110.6514
H(16) C(18) H(14) 110.3213
H(16) C(18) H(15) 105.7444
C(3) C(4) H(3) 119.3479
H(2) C(3) C(4) 120.3505
C(3) C(2) H(1) 121.3822
H(2) C(3) C(2) 118.5530
H(24) C(21) H(23) 109.9013
H(25) C(21) H(23) 105.9769
H(25) C(21) H(24) 108.2537
C(1) C(2) H(1) 120.0416
H(18) C(23) H(17) 106.9879
H(19) C(23) H(17) 106.3526
H(19) C(23) H(18) 107.2965
H(12) C(19) H(11) 110.2287
H(13) C(19) H(11) 106.9061
H(13) C(19) H(12) 107.1087
H(10) C(17) H(9) 112.2190
H(21) C(22) H(20) 110.1395
H(22) C(22) H(20) 105.1978
H(22) C(22) H(21) 111.4501
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S(1) C(7) 1.747(2)
S(1) C(1) 1.730(2)
O(2) O(3) 1.496(2)
O(2) C(15) 1.485(2)
O(3) C(14) 1.470(2)
O(1) C(11) 1.364(2)
O(4) C(14) 1.386(2)
O(4) C(17) 1.445(2)
N(2) C(7) 1.293(2)
N(2) C(6) 1.393(2)
C(13) C(14) 1.525(2)
C(13) C(8) 1.415(2)
C(13) C(12) 1.393(2)
C(15) C(14) 1.587(2)
C(15) C(16) 1.563(2)
C(15) C(20) 1.554(2)
C(16) C(18) 1.532(3)
C(16) C(19) 1.537(3)
C(16) C(17) 1.538(3)
C(11) C(12) 1.395(2)
C(11) C(10) 1.390(3)
C(20) C(21) 1.537(3)
C(20) C(23) 1.533(3)
C(20) C(22) 1.542(3)
C(7) C(8) 1.494(2)
C(8) C(9) 1.394(3)
C(9) C(10) 1.386(3)
C(6) C(5) 1.395(2)
C(6) C(1) 1.398(3)
C(5) C(4) 1.381(3)
C(3) C(4) 1.395(3)
C(3) C(2) 1.369(3)
C(1) C(2) 1.397(3)
O(1) H(8) 0.8907
C(9) H(5) 1.0044
C(5) H(4) 0.9314
C(18) H(14) 1.0263
C(18) H(15) 0.9565
C(18) H(16) 1.0364
C(12) H(7) 0.9560
C(3) H(2) 1.0015
C(21) H(23) 1.0314
C(21) H(24) 1.0231
C(21) H(25) 0.9750
C(23) H(17) 0.9845
C(23) H(18) 0.9820
C(23) H(19) 0.9952
C(19) H(11) 0.9970
C(19) H(12) 1.0307
C(19) H(13) 1.0124
C(10) H(6) 0.9758
C(17) H(9) 1.0243
C(17) H(10) 0.9721
C(22) H(20) 0.9947
C(22) H(21) 1.0748
C(22) H(22) 0.9662
C(4) H(3) 0.9949
C(2) H(1) 0.9740
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
C(1) S(1) C(7) N(2) 1.8(1)
C(1) S(1) C(7) C(8) 174.7(1)
C(7) S(1) C(1) C(6) -1.0(1)
C(7) S(1) C(1) C(2) 178.3(2)
C(15) O(2) O(3) C(14) 4.5(1)
O(3) O(2) C(15) C(14) -4.1(1)
O(3) O(2) C(15) C(16) -107.8(1)
O(3) O(2) C(15) C(20) 118.8(1)
O(2) O(3) C(14) O(4) 104.1(1)
O(2) O(3) C(14) C(13) -137.2(1)
O(2) O(3) C(14) C(15) -4.2(1)
C(17) O(4) C(14) O(3) -70.2(1)
C(17) O(4) C(14) C(13) 169.9(1)
C(17) O(4) C(14) C(15) 25.2(2)
C(14) O(4) C(17) C(16) -39.6(2)
C(6) N(2) C(7) S(1) -2.0(2)
C(6) N(2) C(7) C(8) -174.6(2)
C(7) N(2) C(6) C(5) -178.8(2)
C(7) N(2) C(6) C(1) 1.2(2)
C(8) C(13) C(14) O(3) -156.6(1)
C(8) C(13) C(14) O(4) -35.5(2)
C(8) C(13) C(14) C(15) 97.9(2)
C(12) C(13) C(14) O(3) 18.7(2)
C(12) C(13) C(14) O(4) 139.8(1)
C(12) C(13) C(14) C(15) -86.9(2)
C(14) C(13) C(8) C(7) -5.4(3)
C(14) C(13) C(8) C(9) 176.5(2)
C(12) C(13) C(8) C(7) 179.4(2)
C(12) C(13) C(8) C(9) 1.3(2)
C(14) C(13) C(12) C(11) -176.5(2)
C(8) C(13) C(12) C(11) -1.0(2)
O(2) C(15) C(14) O(3) 4.2(1)
O(2) C(15) C(14) O(4) -107.8(1)
O(2) C(15) C(14) C(13) 118.9(2)
C(16) C(15) C(14) O(3) 110.0(1)
C(16) C(15) C(14) O(4) -2.0(2)
C(16) C(15) C(14) C(13) -135.3(2)
C(20) C(15) C(14) O(3) -106.7(2)
C(20) C(15) C(14) O(4) 141.3(1)
C(20) C(15) C(14) C(13) 8.0(3)
O(2) C(15) C(16) C(18) -171.4(2)
O(2) C(15) C(16) C(19) -44.4(2)
O(2) C(15) C(16) C(17) 71.7(2)
C(14) C(15) C(16) C(18) 97.0(2)
C(14) C(15) C(16) C(19) -136.0(1)
C(14) C(15) C(16) C(17) -19.9(2)
C(20) C(15) C(16) C(18) -46.0(2)
C(20) C(15) C(16) C(19) 81.0(2)
C(20) C(15) C(16) C(17) -162.9(2)
O(2) C(15) C(20) C(21) -43.7(2)
O(2) C(15) C(20) C(23) -163.3(1)
O(2) C(15) C(20) C(22) 73.7(2)
C(14) C(15) C(20) C(21) 55.7(2)
C(14) C(15) C(20) C(23) -63.9(2)
C(14) C(15) C(20) C(22) 173.1(1)
C(16) C(15) C(20) C(21) -167.8(2)
C(16) C(15) C(20) C(23) 72.7(2)
C(16) C(15) C(20) C(22) -50.3(2)
C(15) C(16) C(17) O(4) 35.8(2)
C(18) C(16) C(17) O(4) -84.7(2)
C(19) C(16) C(17) O(4) 156.1(1)
O(1) C(11) C(12) C(13) 179.7(2)
C(10) C(11) C(12) C(13) 0.0(2)
O(1) C(11) C(10) C(9) -179.2(2)
C(12) C(11) C(10) C(9) 0.6(3)
S(1) C(7) C(8) C(13) 101.7(2)
S(1) C(7) C(8) C(9) -80.2(2)
N(2) C(7) C(8) C(13) -86.1(2)
N(2) C(7) C(8) C(9) 92.1(2)
C(13) C(8) C(9) C(10) -0.8(3)
C(7) C(8) C(9) C(10) -179.0(2)
C(8) C(9) C(10) C(11) -0.2(3)
N(2) C(6) C(5) C(4) 178.7(2)
C(1) C(6) C(5) C(4) -1.3(3)
N(2) C(6) C(1) S(1) 0.1(2)
N(2) C(6) C(1) C(2) -179.2(2)
C(5) C(6) C(1) S(1) -179.9(1)
C(5) C(6) C(1) C(2) 0.8(3)
C(6) C(5) C(4) C(3) 0.7(3)
C(2) C(3) C(4) C(5) 0.4(3)
C(4) C(3) C(2) C(1) -0.9(3)
S(1) C(1) C(2) C(3) -178.9(2)
C(6) C(1) C(2) C(3) 0.3(3)
