#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/23/1502317.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_1502317
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 rmad
_chemical_formula_moiety         'C23 H25 N O5 S'
_chemical_formula_sum            'C23 H25 N O5 S'
_chemical_formula_weight         427.50
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2010-09-14 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 116.6900(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.8192(6)
_cell_length_b                   5.6930(2)
_cell_length_c                   14.7334(6)
_cell_measurement_reflns_used    9896
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      132.424
_cell_measurement_theta_min      7.292
_cell_volume                     1035.61(7)
_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_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16746
_diffrn_reflns_theta_full        66.37
_diffrn_reflns_theta_max         66.37
_diffrn_reflns_theta_min         3.65
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.689
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.059
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.004(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3572
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0234
_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)+(0.0317P)²+0.2967P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0609
_refine_ls_wR_factor_ref         0.0611
_reflns_number_gt                3562
_reflns_number_total             3572
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201532k_si_003.cif
_cod_data_source_block           CMLD_SI_08
_cod_database_code               1502317
#BEGIN Tags that were not found in dictionaries:
_publcif_info_exptl_table_max_cols 6
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
S1 S 0.17459(2) 0.24769(6) 0.15158(2) 0.01629(9) Uani 1 1 d .
O1 O 0.13941(8) 0.2486(2) 0.22863(8) 0.0248(2) Uani 1 1 d .
O2 O 0.16673(8) 0.45759(19) 0.09548(8) 0.0222(2) Uani 1 1 d .
O3 O 0.46624(7) 0.42950(18) 0.08560(7) 0.0159(2) Uani 1 1 d .
O4 O 0.64675(7) 0.75804(19) 0.12161(7) 0.0183(2) Uani 1 1 d .
H4 H 0.5955 0.7745 0.0630 0.028 Uiso 1 1 calc R
O5 O 0.76239(8) 0.3855(2) 0.06642(8) 0.0234(2) Uani 1 1 d .
N1 N 0.30441(9) 0.1713(2) 0.20531(9) 0.0172(3) Uani 1 1 d .
C15 C 0.38656(10) 0.2609(3) 0.18291(10) 0.0152(3) Uani 1 1 d .
C16 C 0.48133(11) 0.1540(3) 0.24229(10) 0.0144(3) Uani 1 1 d .
C9 C 0.58655(10) 0.2208(3) 0.24120(10) 0.0145(3) Uani 1 1 d .
H9 H 0.6088 0.0934 0.2077 0.017 Uiso 1 1 calc R
C8 C 0.67496(10) 0.2592(3) 0.34777(10) 0.0158(3) Uani 1 1 d .
H8 H 0.6644 0.3788 0.3874 0.019 Uiso 1 1 calc R
C7 C 0.76626(11) 0.1371(3) 0.38954(10) 0.0164(3) Uani 1 1 d .
H7 H 0.7752 0.0182 0.3487 0.020 Uiso 1 1 calc R
C4 C 0.85536(11) 0.1662(3) 0.49259(10) 0.0165(3) Uani 1 1 d .
C3 C 0.86504(11) 0.3624(3) 0.55351(11) 0.0196(3) Uani 1 1 d .
H3 H 0.8119 0.4828 0.5288 0.024 Uiso 1 1 calc R
C2 C 0.95173(12) 0.3824(3) 0.64966(11) 0.0224(3) Uani 1 1 d .
H2 H 0.9573 0.5159 0.6904 0.027 Uiso 1 1 calc R
C1 C 1.03035(12) 0.2080(3) 0.68646(11) 0.0222(3) Uani 1 1 d .
H1 H 1.0894 0.2215 0.7523 0.027 Uiso 1 1 calc R
C14 C 0.37257(11) 0.4394(3) 0.10337(11) 0.0170(3) Uani 1 1 d .
H14A H 0.3066 0.4045 0.0399 0.020 Uiso 1 1 calc R
H14B H 0.3651 0.5982 0.1268 0.020 Uiso 1 1 calc R
C10 C 0.56521(11) 0.4488(3) 0.17850(10) 0.0147(3) Uani 1 1 d .
H10 H 0.5564 0.5797 0.2194 0.018 Uiso 1 1 calc R
C11 C 0.65529(11) 0.5168(3) 0.15064(10) 0.0151(3) Uani 1 1 d .
H11 H 0.7254 0.4984 0.2134 0.018 Uiso 1 1 calc R
C12 C 0.66126(11) 0.3592(3) 0.06933(11) 0.0178(3) Uani 1 1 d .
H12A H 0.6519 0.1933 0.0838 0.021 Uiso 1 1 calc R
H12B H 0.6016 0.4001 0.0022 0.021 Uiso 1 1 calc R
C13 C 0.84122(12) 0.2213(3) 0.13055(11) 0.0256(3) Uani 1 1 d .
H13A H 0.8397 0.2144 0.1964 0.038 Uiso 1 1 calc R
H13C H 0.9133 0.2710 0.1406 0.038 Uiso 1 1 calc R
H13B H 0.8249 0.0656 0.0988 0.038 Uiso 1 1 calc R
C17 C 0.46136(11) -0.0196(2) 0.30356(10) 0.0146(3) Uani 1 1 d .
C22 C 0.35069(11) -0.0078(3) 0.27888(10) 0.0168(3) Uani 1 1 d .
C21 C 0.30227(12) -0.1604(3) 0.32025(11) 0.0204(3) Uani 1 1 d .
H21 H 0.2272 -0.1505 0.3024 0.024 Uiso 1 1 calc R
C20 C 0.36800(12) -0.3271(3) 0.38851(11) 0.0213(3) Uani 1 1 d .
H20 H 0.3373 -0.4353 0.4174 0.026 Uiso 1 1 calc R
C19 C 0.47947(12) -0.3393(3) 0.41596(11) 0.0192(3) Uani 1 1 d .
H19 H 0.5230 -0.4541 0.4636 0.023 Uiso 1 1 calc R
C18 C 0.52617(11) -0.1862(3) 0.37436(10) 0.0167(3) Uani 1 1 d .
H18 H 0.6016 -0.1942 0.3937 0.020 Uiso 1 1 calc R
C5 C 0.93542(12) -0.0068(3) 0.53062(11) 0.0187(3) Uani 1 1 d .
H5 H 0.9305 -0.1407 0.4903 0.022 Uiso 1 1 calc R
C6 C 1.02197(12) 0.0146(3) 0.62651(11) 0.0222(3) Uani 1 1 d .
H6 H 1.0759 -0.1044 0.6512 0.027 Uiso 1 1 calc R
C23 C 0.11045(13) 0.0188(3) 0.06637(12) 0.0261(4) Uani 1 1 d .
H23A H 0.0322 0.0473 0.0320 0.039 Uiso 1 1 calc R
H23C H 0.1249 -0.1302 0.1035 0.039 Uiso 1 1 calc R
H23B H 0.1383 0.0109 0.0159 0.039 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 S1 O2 119.62(7)
O1 S1 N1 107.70(6)
O2 S1 N1 106.26(6)
O1 S1 C23 109.34(8)
O2 S1 C23 108.99(7)
N1 S1 C23 103.74(7)
C14 O3 C10 111.94(10)
C11 O4 H4 109.5
C13 O5 C12 112.31(11)
C15 N1 C22 107.77(11)
C15 N1 S1 127.12(10)
C22 N1 S1 125.03(10)
C16 C15 N1 109.47(12)
C16 C15 C14 124.07(12)
N1 C15 C14 126.42(12)
C15 C16 C17 108.13(12)
C15 C16 C9 122.56(13)
C17 C16 C9 129.30(12)
C16 C9 C8 111.01(10)
C16 C9 C10 106.99(11)
C8 C9 C10 110.37(12)
C16 C9 H9 109.5
C8 C9 H9 109.5
C10 C9 H9 109.5
C7 C8 C9 124.28(13)
C7 C8 H8 117.9
C9 C8 H8 117.9
C8 C7 C4 126.90(13)
C8 C7 H7 116.5
C4 C7 H7 116.5
C5 C4 C3 118.32(13)
C5 C4 C7 118.64(13)
C3 C4 C7 123.02(13)
C2 C3 C4 120.61(14)
C2 C3 H3 119.7
C4 C3 H3 119.7
C3 C2 C1 120.28(14)
C3 C2 H2 119.9
C1 C2 H2 119.9
C6 C1 C2 119.54(13)
C6 C1 H1 120.2
C2 C1 H1 120.2
O3 C14 C15 107.88(11)
O3 C14 H14A 110.1
C15 C14 H14A 110.1
O3 C14 H14B 110.1
C15 C14 H14B 110.1
H14A C14 H14B 108.4
O3 C10 C11 107.76(11)
O3 C10 C9 110.45(11)
C11 C10 C9 114.52(11)
O3 C10 H10 108.0
C11 C10 H10 108.0
C9 C10 H10 108.0
O4 C11 C10 110.92(11)
O4 C11 C12 110.86(11)
C10 C11 C12 113.58(12)
O4 C11 H11 107.0
C10 C11 H11 107.0
C12 C11 H11 107.0
O5 C12 C11 111.17(12)
O5 C12 H12A 109.4
C11 C12 H12A 109.4
O5 C12 H12B 109.4
C11 C12 H12B 109.4
H12A C12 H12B 108.0
O5 C13 H13A 109.5
O5 C13 H13C 109.5
H13A C13 H13C 109.5
O5 C13 H13B 109.5
H13A C13 H13B 109.5
H13C C13 H13B 109.5
C18 C17 C22 118.92(13)
C18 C17 C16 133.80(13)
C22 C17 C16 107.25(12)
C21 C22 C17 122.53(13)
C21 C22 N1 130.10(13)
C17 C22 N1 107.31(12)
C20 C21 C22 117.26(13)
C20 C21 H21 121.4
C22 C21 H21 121.4
C21 C20 C19 121.25(14)
C21 C20 H20 119.4
C19 C20 H20 119.4
C18 C19 C20 120.70(14)
C18 C19 H19 119.6
C20 C19 H19 119.6
C19 C18 C17 119.31(13)
C19 C18 H18 120.3
C17 C18 H18 120.3
C6 C5 C4 120.81(14)
C6 C5 H5 119.6
C4 C5 H5 119.6
C1 C6 C5 120.45(14)
C1 C6 H6 119.8
C5 C6 H6 119.8
S1 C23 H23A 109.5
S1 C23 H23C 109.5
H23A C23 H23C 109.5
S1 C23 H23B 109.5
H23A C23 H23B 109.5
H23C C23 H23B 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4216(10)
S1 O2 1.4290(11)
S1 N1 1.6608(12)
S1 C23 1.7496(16)
O3 C14 1.4324(17)
O3 C10 1.4403(16)
O4 C11 1.4276(18)
O4 H4 0.8400
O5 C13 1.4242(19)
O5 C12 1.4251(16)
N1 C15 1.4124(18)
N1 C22 1.4144(19)
C15 C16 1.350(2)
C15 C14 1.496(2)
C16 C17 1.446(2)
C16 C9 1.5100(18)
C9 C8 1.5109(18)
C9 C10 1.5430(19)
C9 H9 1.0000
C8 C7 1.325(2)
C8 H8 0.9500
C7 C4 1.4729(19)
C7 H7 0.9500
C4 C5 1.397(2)
C4 C3 1.401(2)
C3 C2 1.389(2)
C3 H3 0.9500
C2 C1 1.389(2)
C2 H2 0.9500
C1 C6 1.384(2)
C1 H1 0.9500
C14 H14A 0.9900
C14 H14B 0.9900
C10 C11 1.5254(19)
C10 H10 1.0000
C11 C12 1.5279(19)
C11 H11 1.0000
C12 H12A 0.9900
C12 H12B 0.9900
C13 H13A 0.9800
C13 H13C 0.9800
C13 H13B 0.9800
C17 C18 1.397(2)
C17 C22 1.406(2)
C22 C21 1.393(2)
C21 C20 1.384(2)
C21 H21 0.9500
C20 C19 1.408(2)
C20 H20 0.9500
C19 C18 1.381(2)
C19 H19 0.9500
C18 H18 0.9500
C5 C6 1.387(2)
C5 H5 0.9500
C6 H6 0.9500
C23 H23A 0.9800
C23 H23C 0.9800
C23 H23B 0.9800
#BEGIN Loops that were not found in dictionaries:
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
CMLD_SI-08 y y y
#END Loops that were not found in dictionaries
