#------------------------------------------------------------------------------
#$Date: 2019-11-04 14:37:23 +0200 (Mon, 04 Nov 2019) $
#$Revision: 223038 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/45/4034539.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_4034539
loop_
_publ_author_name
'Hugelshofer, Cedric L.'
'Palani, Vignesh'
'Sarpong, Richmond'
_publ_section_title
;
 Calyciphylline B-type Alkaloids: Evolution of a Synthetic Strategy to
 (-)-Daphlongamine H.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14069
_journal_page_last               14091
_journal_paper_doi               10.1021/acs.joc.9b02223
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H21 N O3 S'
_chemical_formula_sum            'C13 H21 N O3 S'
_chemical_formula_weight         271.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.17650(10)
_cell_length_b                   9.22680(10)
_cell_length_c                   24.6586(2)
_cell_measurement_reflns_used    13695
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.7500
_cell_measurement_theta_min      4.8220
_cell_volume                     1405.28(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            14126
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        74.000
_diffrn_reflns_theta_max         74.496
_diffrn_reflns_theta_min         5.118
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    2.060
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1175 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2854
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0249
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0382P)²+0.4717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0660
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2854
_reflns_number_total             2854
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b02223_si_002.cif
_cod_data_source_block           CH6_131p
_cod_database_code               4034539
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.533
_shelx_estimated_absorpt_t_max   0.708
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.3549(4) 0.0751(2) 0.72114(8) 0.0211(4) Uani 1 1 d . .
H1A H 0.3953 0.0204 0.6886 0.032 Uiso 1 1 calc R U
H1B H 0.2560 0.0170 0.7433 0.032 Uiso 1 1 calc R U
H1C H 0.4853 0.0977 0.7422 0.032 Uiso 1 1 calc R U
C2 C 0.2430(3) 0.21599(19) 0.70447(7) 0.0168(4) Uani 1 1 d . .
C3 C 0.1833(3) 0.3045(2) 0.75448(8) 0.0240(4) Uani 1 1 d . .
H3A H 0.3151 0.3296 0.7745 0.036 Uiso 1 1 calc R U
H3B H 0.0874 0.2473 0.7778 0.036 Uiso 1 1 calc R U
H3C H 0.1090 0.3934 0.7433 0.036 Uiso 1 1 calc R U
C4 C 0.0494(3) 0.1857(2) 0.66800(9) 0.0272(4) Uani 1 1 d . .
H4A H -0.0165 0.2775 0.6568 0.041 Uiso 1 1 calc R U
H4B H -0.0573 0.1277 0.6879 0.041 Uiso 1 1 calc R U
H4C H 0.0974 0.1322 0.6358 0.041 Uiso 1 1 calc R U
C5 C 0.4629(3) 0.58362(18) 0.63413(7) 0.0137(3) Uani 1 1 d . .
H5 H 0.5941 0.5867 0.6579 0.016 Uiso 1 1 calc R U
C6 C 0.3576(3) 0.7309(2) 0.63684(8) 0.0183(4) Uani 1 1 d . .
H6 H 0.2559 0.7591 0.6638 0.022 Uiso 1 1 calc R U
C7 C 0.4247(3) 0.8160(2) 0.59696(8) 0.0205(4) Uani 1 1 d . .
H7 H 0.3820 0.9143 0.5928 0.025 Uiso 1 1 calc R U
C8 C 0.5756(3) 0.73903(19) 0.55913(8) 0.0186(4) Uani 1 1 d . .
H8A H 0.7273 0.7696 0.5652 0.022 Uiso 1 1 calc R U
H8B H 0.5365 0.7578 0.5208 0.022 Uiso 1 1 calc R U
C9 C 0.5436(3) 0.57575(18) 0.57385(7) 0.0131(3) Uani 1 1 d . .
C10 C 0.7646(3) 0.50187(19) 0.57167(7) 0.0162(3) Uani 1 1 d . .
C11 C 0.6596(3) 0.3658(2) 0.49062(8) 0.0199(4) Uani 1 1 d . .
H11A H 0.5992 0.2739 0.5048 0.024 Uiso 1 1 calc R U
H11B H 0.7311 0.3445 0.4556 0.024 Uiso 1 1 calc R U
C12 C 0.4774(3) 0.4718(2) 0.48128(7) 0.0182(4) Uani 1 1 d . .
H12A H 0.3678 0.4286 0.4568 0.022 Uiso 1 1 calc R U
H12B H 0.5339 0.5611 0.4641 0.022 Uiso 1 1 calc R U
C13 C 0.3752(3) 0.5078(2) 0.53589(7) 0.0145(3) Uani 1 1 d . .
H13A H 0.3168 0.4183 0.5525 0.017 Uiso 1 1 calc R U
H13B H 0.2537 0.5763 0.5305 0.017 Uiso 1 1 calc R U
N1 N 0.3246(2) 0.46642(16) 0.65397(6) 0.0141(3) Uani 1 1 d . .
O1 O 0.4951(2) 0.22699(14) 0.61650(5) 0.0194(3) Uani 1 1 d . .
O2 O 0.8992(2) 0.52285(16) 0.60642(6) 0.0225(3) Uani 1 1 d . .
O3 O 0.8210(2) 0.42142(15) 0.52893(5) 0.0204(3) Uani 1 1 d . .
S1 S 0.45717(6) 0.31332(4) 0.66691(2) 0.01336(12) Uani 1 1 d . .
H1 H 0.194(4) 0.455(3) 0.6362(10) 0.021(6) Uiso 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 0.0181 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
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C4 C2 C3 112.74(17)
C4 C2 C1 110.98(16)
C3 C2 C1 110.31(15)
C4 C2 S1 110.83(13)
C3 C2 S1 108.57(13)
C1 C2 S1 102.95(13)
C2 C3 H3A 109.5
C2 C3 H3B 109.5
H3A C3 H3B 109.5
C2 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
C2 C4 H4A 109.5
C2 C4 H4B 109.5
H4A C4 H4B 109.5
C2 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
N1 C5 C6 113.55(15)
N1 C5 C9 117.92(14)
C6 C5 C9 102.76(13)
N1 C5 H5 107.4
C6 C5 H5 107.4
C9 C5 H5 107.4
C7 C6 C5 111.47(16)
C7 C6 H6 124.3
C5 C6 H6 124.3
C6 C7 C8 112.10(16)
C6 C7 H7 124.0
C8 C7 H7 124.0
C7 C8 C9 103.50(14)
C7 C8 H8A 111.1
C9 C8 H8A 111.1
C7 C8 H8B 111.1
C9 C8 H8B 111.1
H8A C8 H8B 109.0
C10 C9 C13 113.73(14)
C10 C9 C8 108.02(14)
C13 C9 C8 109.76(14)
C10 C9 C5 109.77(14)
C13 C9 C5 112.43(15)
C8 C9 C5 102.46(13)
O2 C10 O3 117.96(16)
O2 C10 C9 121.21(16)
O3 C10 C9 120.61(15)
O3 C11 C12 112.24(15)
O3 C11 H11A 109.2
C12 C11 H11A 109.2
O3 C11 H11B 109.2
C12 C11 H11B 109.2
H11A C11 H11B 107.9
C11 C12 C13 108.39(14)
C11 C12 H12A 110.0
C13 C12 H12A 110.0
C11 C12 H12B 110.0
C13 C12 H12B 110.0
H12A C12 H12B 108.4
C12 C13 C9 110.35(15)
C12 C13 H13A 109.6
C9 C13 H13A 109.6
C12 C13 H13B 109.6
C9 C13 H13B 109.6
H13A C13 H13B 108.1
C5 N1 S1 113.87(12)
C5 N1 H1 115.9(15)
S1 N1 H1 114.9(15)
C10 O3 C11 121.73(14)
O1 S1 N1 111.72(7)
O1 S1 C2 105.66(8)
N1 S1 C2 98.99(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.529(3)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C4 1.522(3)
C2 C3 1.524(3)
C2 S1 1.8479(19)
C3 H3A 0.9800
C3 H3B 0.9800
C3 H3C 0.9800
C4 H4A 0.9800
C4 H4B 0.9800
C4 H4C 0.9800
C5 N1 1.462(2)
C5 C6 1.508(2)
C5 C9 1.569(2)
C5 H5 1.0000
C6 C7 1.325(3)
C6 H6 0.9500
C7 C8 1.498(3)
C7 H7 0.9500
C8 C9 1.562(2)
C8 H8A 0.9900
C8 H8B 0.9900
C9 C10 1.526(2)
C9 C13 1.533(2)
C10 O2 1.210(2)
C10 O3 1.335(2)
C11 O3 1.466(2)
C11 C12 1.508(3)
C11 H11A 0.9900
C11 H11B 0.9900
C12 C13 1.524(2)
C12 H12A 0.9900
C12 H12B 0.9900
C13 H13A 0.9900
C13 H13B 0.9900
N1 S1 1.6637(15)
N1 H1 0.92(3)
O1 S1 1.4946(12)
