#------------------------------------------------------------------------------
#$Date: 2025-08-18 15:30:32 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301775 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/23/1502316.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_1502316
loop_
_publ_author_name
'Medeiros, Matthew R.'
'Schaus, Scott E.'
'Porco, Jr, John A'
_publ_contact_author             'John A. Porco, Jr.'
_publ_section_title
;
 A cycloisomerization/Friedel-Crafts alkylation strategy for the synthesis
 of pyrano[3,4-b]indoles.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              4012
_journal_page_last               4015
_journal_paper_doi               10.1021/ol201532k
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H24 Cl N O5 S'
_chemical_formula_sum            'C23 H24 Cl N O5 S'
_chemical_formula_weight         461.94
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2011-04-20 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.1760(2)
_cell_length_b                   9.5637(4)
_cell_length_c                   44.8293(18)
_cell_measurement_reflns_used    9791
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.73
_cell_measurement_theta_min      3.94
_cell_volume                     2219.13(15)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'OLEX2 (Dolmanov, et al. 2009)'
_computing_publication_material  'PublCIF v.1.9.5_c (IUCr)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Proteum-R'
_diffrn_measurement_method       'ω & φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            30718
_diffrn_reflns_theta_full        66.35
_diffrn_reflns_theta_max         66.35
_diffrn_reflns_theta_min         3.94
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.701
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.088
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.027
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.030(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3859
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0384
_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)+(0.0669P)²+0.4888P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1027
_reflns_number_gt                3794
_reflns_number_total             3859
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201532k_si_002.cif
_cod_data_source_block           CMLD_25d
_cod_database_code               1502316
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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
Cl1 Cl 0.28781(18) -0.16940(6) 0.027799(16) 0.0559(2) Uani 1 1 d .
S1 S 0.52956(10) 0.41911(6) 0.043076(11) 0.02907(15) Uani 1 1 d .
O5 O 0.1327(3) 0.57031(18) 0.13082(3) 0.0308(3) Uani 1 1 d .
O4 O -0.4618(3) 0.49606(19) 0.17067(3) 0.0354(4) Uani 1 1 d .
H4 H -0.5759 0.5334 0.1600 0.053 Uiso 1 1 calc R
O3 O -0.4132(4) 0.7611(2) 0.14321(4) 0.0425(4) Uani 1 1 d .
O2 O 0.6318(3) 0.54345(18) 0.05607(3) 0.0357(4) Uani 1 1 d .
O1 O 0.7003(3) 0.31778(19) 0.03067(4) 0.0393(4) Uani 1 1 d .
N1 N 0.3618(4) 0.3383(2) 0.06977(4) 0.0306(4) Uani 1 1 d .
C20 C 0.2102(6) -0.0329(3) 0.05218(5) 0.0398(6) Uani 1 1 d .
C21 C 0.0222(6) -0.0549(2) 0.07379(6) 0.0414(6) Uani 1 1 d .
H21 H -0.0640 -0.1424 0.0752 0.050 Uiso 1 1 calc R
C22 C -0.0379(5) 0.0522(2) 0.09326(5) 0.0377(5) Uani 1 1 d .
H22 H -0.1629 0.0383 0.1085 0.045 Uiso 1 1 calc R
C17 C 0.0859(4) 0.1808(2) 0.09046(5) 0.0301(5) Uani 1 1 d .
C7 C 0.0593(4) 0.3120(2) 0.10566(5) 0.0299(5) Uani 1 1 d .
C8 C -0.0954(5) 0.3462(3) 0.13315(5) 0.0324(5) Uani 1 1 d .
H8 H -0.2723 0.3051 0.1313 0.039 Uiso 1 1 calc R
C9 C 0.0410(5) 0.2840(3) 0.16009(5) 0.0347(5) Uani 1 1 d .
H9 H 0.2143 0.3124 0.1635 0.042 Uiso 1 1 calc R
C10 C -0.0588(5) 0.1948(3) 0.17896(5) 0.0366(5) Uani 1 1 d .
H10 H -0.2318 0.1657 0.1756 0.044 Uiso 1 1 calc R
C11 C 0.0765(5) 0.1358(3) 0.20510(5) 0.0366(5) Uani 1 1 d .
C16 C -0.0172(6) 0.0161(3) 0.21873(6) 0.0461(6) Uani 1 1 d .
H16 H -0.1656 -0.0287 0.2107 0.055 Uiso 1 1 calc R
C15 C 0.1010(7) -0.0395(3) 0.24379(7) 0.0559(8) Uani 1 1 d .
H15 H 0.0339 -0.1216 0.2528 0.067 Uiso 1 1 calc R
C14 C 0.3145(6) 0.0243(3) 0.25544(6) 0.0518(7) Uani 1 1 d .
H14 H 0.3959 -0.0137 0.2726 0.062 Uiso 1 1 calc R
C18 C 0.2726(5) 0.1987(2) 0.06798(5) 0.0308(5) Uani 1 1 d .
C6 C 0.2177(4) 0.4057(2) 0.09264(4) 0.0275(4) Uani 1 1 d .
C5 C 0.2284(5) 0.5573(2) 0.10116(5) 0.0300(5) Uani 1 1 d .
H5A H 0.4086 0.5917 0.1001 0.036 Uiso 1 1 calc R
H5B H 0.1214 0.6134 0.0873 0.036 Uiso 1 1 calc R
C4 C -0.1151(4) 0.5067(3) 0.13491(5) 0.0299(5) Uani 1 1 d .
H4A H -0.2326 0.5398 0.1187 0.036 Uiso 1 1 calc R
C3 C -0.2194(5) 0.5602(3) 0.16486(5) 0.0337(5) Uani 1 1 d .
H3 H -0.0965 0.5303 0.1808 0.040 Uiso 1 1 calc R
C2 C -0.2431(5) 0.7174(3) 0.16620(5) 0.0394(6) Uani 1 1 d .
H2A H -0.3116 0.7463 0.1859 0.047 Uiso 1 1 calc R
H2B H -0.0713 0.7610 0.1634 0.047 Uiso 1 1 calc R
C1 C -0.5306(6) 0.8899(3) 0.14919(7) 0.0490(7) Uani 1 1 d .
H1A H -0.6266 0.8839 0.1680 0.074 Uiso 1 1 calc R
H1B H -0.6496 0.9135 0.1329 0.074 Uiso 1 1 calc R
H1C H -0.3977 0.9625 0.1508 0.074 Uiso 1 1 calc R
C13 C 0.4119(6) 0.1429(3) 0.24242(5) 0.0458(6) Uani 1 1 d .
H13 H 0.5599 0.1872 0.2507 0.055 Uiso 1 1 calc R
C12 C 0.2948(5) 0.1981(3) 0.21731(5) 0.0393(6) Uani 1 1 d .
H12 H 0.3645 0.2797 0.2083 0.047 Uiso 1 1 calc R
C23 C 0.2908(5) 0.4610(3) 0.01673(5) 0.0347(5) Uani 1 1 d .
H23A H 0.3710 0.5075 -0.0004 0.052 Uiso 1 1 calc R
H23B H 0.1635 0.5238 0.0258 0.052 Uiso 1 1 calc R
H23C H 0.2047 0.3753 0.0101 0.052 Uiso 1 1 calc R
C19 C 0.3403(5) 0.0922(3) 0.04872(5) 0.0374(5) Uani 1 1 d .
H19 H 0.4694 0.1043 0.0339 0.045 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
O1 S1 O2 119.78(11)
O1 S1 N1 106.72(10)
O2 S1 N1 106.65(9)
O1 S1 C23 109.22(11)
O2 S1 C23 110.22(11)
N1 S1 C23 102.83(11)
C5 O5 C4 113.22(16)
C3 O4 H4 109.5
C1 O3 C2 112.9(2)
C18 N1 C6 107.35(18)
C18 N1 S1 124.49(15)
C6 N1 S1 125.41(16)
C19 C20 C21 123.4(2)
C19 C20 Cl1 117.7(2)
C21 C20 Cl1 118.93(19)
C22 C21 C20 119.1(2)
C22 C21 H21 120.5
C20 C21 H21 120.5
C21 C22 C17 119.6(2)
C21 C22 H22 120.2
C17 C22 H22 120.2
C22 C17 C18 119.2(2)
C22 C17 C7 133.3(2)
C18 C17 C7 107.4(2)
C6 C7 C17 108.5(2)
C6 C7 C8 122.2(2)
C17 C7 C8 129.0(2)
C7 C8 C9 108.6(2)
C7 C8 C4 107.07(19)
C9 C8 C4 112.36(19)
C7 C8 H8 109.6
C9 C8 H8 109.6
C4 C8 H8 109.6
C10 C9 C8 125.9(2)
C10 C9 H9 117.1
C8 C9 H9 117.1
C9 C10 C11 125.1(2)
C9 C10 H10 117.4
C11 C10 H10 117.4
C16 C11 C12 117.7(2)
C16 C11 C10 120.0(2)
C12 C11 C10 122.3(2)
C11 C16 C15 121.4(3)
C11 C16 H16 119.3
C15 C16 H16 119.3
C14 C15 C16 119.7(3)
C14 C15 H15 120.1
C16 C15 H15 120.1
C15 C14 C13 120.3(3)
C15 C14 H14 119.9
C13 C14 H14 119.9
C19 C18 C17 122.2(2)
C19 C18 N1 130.5(2)
C17 C18 N1 107.36(19)
C7 C6 N1 109.2(2)
C7 C6 C5 123.7(2)
N1 C6 C5 127.1(2)
O5 C5 C6 108.00(18)
O5 C5 H5A 110.1
C6 C5 H5A 110.1
O5 C5 H5B 110.1
C6 C5 H5B 110.1
H5A C5 H5B 108.4
O5 C4 C3 106.62(18)
O5 C4 C8 110.95(19)
C3 C4 C8 113.6(2)
O5 C4 H4A 108.5
C3 C4 H4A 108.5
C8 C4 H4A 108.5
O4 C3 C2 110.5(2)
O4 C3 C4 109.14(18)
C2 C3 C4 113.3(2)
O4 C3 H3 107.9
C2 C3 H3 107.9
C4 C3 H3 107.9
O3 C2 C3 108.35(19)
O3 C2 H2A 110.0
C3 C2 H2A 110.0
O3 C2 H2B 110.0
C3 C2 H2B 110.0
H2A C2 H2B 108.4
O3 C1 H1A 109.5
O3 C1 H1B 109.5
H1A C1 H1B 109.5
O3 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C14 C13 C12 120.0(3)
C14 C13 H13 120.0
C12 C13 H13 120.0
C13 C12 C11 120.9(3)
C13 C12 H12 119.6
C11 C12 H12 119.6
S1 C23 H23A 109.5
S1 C23 H23B 109.5
H23A C23 H23B 109.5
S1 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
C18 C19 C20 116.4(2)
C18 C19 H19 121.8
C20 C19 H19 121.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C20 1.749(2)
S1 O1 1.4245(18)
S1 O2 1.4260(18)
S1 N1 1.6686(19)
S1 C23 1.756(2)
O5 C5 1.425(3)
O5 C4 1.431(3)
O4 C3 1.420(3)
O4 H4 0.8400
O3 C1 1.399(3)
O3 C2 1.419(3)
N1 C18 1.415(3)
N1 C6 1.423(3)
C20 C19 1.382(4)
C20 C21 1.389(4)
C21 C22 1.381(3)
C21 H21 0.9500
C22 C17 1.392(3)
C22 H22 0.9500
C17 C18 1.407(3)
C17 C7 1.435(3)
C7 C6 1.348(3)
C7 C8 1.506(3)
C8 C9 1.520(3)
C8 C4 1.540(3)
C8 H8 1.0000
C9 C10 1.307(3)
C9 H9 0.9500
C10 C11 1.477(3)
C10 H10 0.9500
C11 C16 1.385(4)
C11 C12 1.390(4)
C16 C15 1.385(4)
C16 H16 0.9500
C15 C14 1.366(5)
C15 H15 0.9500
C14 C13 1.372(4)
C14 H14 0.9500
C18 C19 1.380(3)
C6 C5 1.500(3)
C5 H5A 0.9900
C5 H5B 0.9900
C4 C3 1.535(3)
C4 H4A 1.0000
C3 C2 1.510(4)
C3 H3 1.0000
C2 H2A 0.9900
C2 H2B 0.9900
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C13 C12 1.383(4)
C13 H13 0.9500
C12 H12 0.9500
C23 H23A 0.9800
C23 H23B 0.9800
C23 H23C 0.9800
C19 H19 0.9500
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139037348
