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#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/79/1507953.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_1507953
loop_
_publ_author_name
'Cakmak, Mesut'
'Mayer, Peter'
'Trauner, Dirk'
_publ_section_title
;
 An efficient synthesis of loline alkaloids.
;
_journal_issue                   7
_journal_name_full               'Nature chemistry'
_journal_page_first              543
_journal_page_last               545
_journal_paper_doi               10.1038/nchem.1072
_journal_volume                  3
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H20 N4 O5 S'
_chemical_formula_sum            'C16 H20 N4 O5 S'
_chemical_formula_weight         380.420
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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_block_code                C16H20N4O5S_on054_trauner
_audit_creation_date             30-Mar-10
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_audit_update_record             08-Apr-10
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.33300(10)
_cell_length_b                   10.3246(2)
_cell_length_c                   26.9497(4)
_cell_measurement_reflns_used    6607
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      3.134
_cell_volume                     1762.12(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement
;
Sheldrick, G. M. (2008).
Acta Cryst. A64, 112--122.
;
_computing_structure_solution
;
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A.
Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for
crystal structure determination and refinement; J. Appl. Crystallogr. 1999,
32, 115-119.
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD; rotation images; thick slices'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.0302225
_diffrn_orient_matrix_UB_12      -0.0789841
_diffrn_orient_matrix_UB_13      0.0202683
_diffrn_orient_matrix_UB_21      -0.0355479
_diffrn_orient_matrix_UB_22      0.0559973
_diffrn_orient_matrix_UB_23      0.0291008
_diffrn_orient_matrix_UB_31      -0.1508520
_diffrn_orient_matrix_UB_32      0.0026285
_diffrn_orient_matrix_UB_33      -0.0109182
_diffrn_radiation_collimation    0.20
_diffrn_radiation_monochromator  'MONTEL, graded multilayered X-ray optics'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            12280
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.30
_diffrn_source_current           55.00
_diffrn_source_power             3.025
_diffrn_source_type              'FR 591 generator'
_diffrn_source_voltage           55.00
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.43397(4)
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4015
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0290
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0308P)²+0.3091P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0698
_reflns_number_gt                3754
_reflns_number_total             4015
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            nchem.1072-s3.cif
_cod_data_source_block           on054
_cod_original_cell_volume        1762.13(5)
_cod_database_code               1507953
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
S1 S 0.84768(6) 0.53176(3) 0.211009(13) 0.02161(9) Uani 1 1 d .
O1 O 0.48387(17) 1.09399(10) 0.14723(4) 0.0284(2) Uani 1 1 d .
O2 O 0.71387(16) 0.96346(11) 0.18844(4) 0.0289(2) Uani 1 1 d .
O3 O 0.62011(16) 0.56467(9) 0.19089(4) 0.0235(2) Uani 1 1 d .
O4 O 1.00018(18) 0.55316(11) 0.17283(4) 0.0294(2) Uani 1 1 d .
O5 O 0.8271(2) 0.40545(10) 0.23150(4) 0.0299(3) Uani 1 1 d .
N1 N 0.39613(19) 0.88757(12) 0.16197(5) 0.0224(3) Uani 1 1 d .
N2 N 0.6298(2) 0.50655(12) 0.09173(5) 0.0300(3) Uani 1 1 d .
N3 N 0.8005(2) 0.53194(13) 0.07163(5) 0.0290(3) Uani 1 1 d .
N4 N 0.9586(3) 0.53974(16) 0.05220(5) 0.0380(3) Uani 1 1 d .
C1 C 0.4361(2) 0.76325(14) 0.18563(6) 0.0234(3) Uani 1 1 d .
H1A H 0.3000 0.7172 0.1896 0.028 Uiso 1 1 calc R
H1B H 0.4938 0.7791 0.2192 0.028 Uiso 1 1 calc R
C2 C 0.5891(2) 0.67522(14) 0.15734(5) 0.0214(3) Uani 1 1 d .
H2 H 0.7261 0.7209 0.1514 0.026 Uiso 1 1 calc R
C3 C 0.5025(3) 0.61970(15) 0.10834(5) 0.0248(3) Uani 1 1 d .
H3 H 0.3564 0.5876 0.1151 0.030 Uiso 1 1 calc R
C4 C 0.4854(3) 0.72169(15) 0.06823(5) 0.0279(3) Uani 1 1 d .
H4 H 0.5990 0.7287 0.0454 0.033 Uiso 1 1 calc R
C5 C 0.3233(3) 0.80222(16) 0.06261(6) 0.0290(3) Uani 1 1 d .
H5 H 0.3222 0.8572 0.0343 0.035 Uiso 1 1 calc R
C6 C 0.1438(3) 0.81142(15) 0.09790(6) 0.0283(3) Uani 1 1 d .
H6A H 0.1176 0.7253 0.1129 0.034 Uiso 1 1 calc R
H6B H 0.0148 0.8377 0.0797 0.034 Uiso 1 1 calc R
C7 C 0.1892(2) 0.90957(15) 0.13893(6) 0.0269(3) Uani 1 1 d .
H7A H 0.1848 0.9981 0.1248 0.032 Uiso 1 1 calc R
H7B H 0.0779 0.9034 0.1646 0.032 Uiso 1 1 calc R
C8 C 0.5456(2) 0.97932(15) 0.16743(5) 0.0224(3) Uani 1 1 d .
C9 C 0.6412(3) 1.19507(15) 0.14605(6) 0.0285(3) Uani 1 1 d .
H9A H 0.7150 1.1977 0.1784 0.034 Uiso 1 1 calc R
H9B H 0.5701 1.2795 0.1412 0.034 Uiso 1 1 calc R
C10 C 0.8013(3) 1.17614(14) 0.10547(6) 0.0254(3) Uani 1 1 d .
C11 C 0.9881(3) 1.24698(15) 0.10704(6) 0.0297(3) Uani 1 1 d .
H11 H 1.0157 1.3023 0.1345 0.036 Uiso 1 1 calc R
C12 C 1.1344(3) 1.23759(16) 0.06895(7) 0.0359(4) Uani 1 1 d .
H12 H 1.2609 1.2870 0.0702 0.043 Uiso 1 1 calc R
C13 C 1.0962(3) 1.15613(17) 0.02906(7) 0.0388(4) Uani 1 1 d .
H13 H 1.1964 1.1494 0.0030 0.047 Uiso 1 1 calc R
C14 C 0.9122(3) 1.08500(18) 0.02743(7) 0.0399(4) Uani 1 1 d .
H14 H 0.8865 1.0286 0.0002 0.048 Uiso 1 1 calc R
C15 C 0.7644(3) 1.09507(16) 0.06508(6) 0.0330(4) Uani 1 1 d .
H15 H 0.6372 1.0465 0.0634 0.040 Uiso 1 1 calc R
C16 C 0.8893(3) 0.64442(16) 0.25835(6) 0.0325(4) Uani 1 1 d .
H16A H 0.7748 0.6382 0.2827 0.049 Uiso 1 1 calc R
H16B H 0.8921 0.7319 0.2443 0.049 Uiso 1 1 calc R
H16C H 1.0244 0.6264 0.2747 0.049 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 0.0033 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-6 0 1 0.102000
6 0 1 0.152000
0 1 -16 0.061000
0 -1 16 0.027000
0 -3 -2 0.027000
0 2 1 0.014000
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O5 S1 O4 118.91(7)
O5 S1 O3 104.31(7)
O4 S1 O3 109.69(6)
O5 S1 C16 109.93(8)
O4 S1 C16 108.74(8)
O3 S1 C16 104.22(7)
C8 O1 C9 116.09(12)
C2 O3 S1 120.06(9)
C8 N1 C1 116.76(12)
C8 N1 C7 124.38(12)
C1 N1 C7 118.49(12)
N3 N2 C3 116.03(13)
N4 N3 N2 171.79(17)
N1 C1 C2 114.54(12)
N1 C1 H1A 108.6
C2 C1 H1A 108.6
N1 C1 H1B 108.6
C2 C1 H1B 108.6
H1A C1 H1B 107.6
O3 C2 C1 103.84(11)
O3 C2 C3 106.62(11)
C1 C2 C3 114.95(13)
O3 C2 H2 110.4
C1 C2 H2 110.4
C3 C2 H2 110.4
N2 C3 C4 111.72(12)
N2 C3 C2 110.90(13)
C4 C3 C2 112.27(12)
N2 C3 H3 107.2
C4 C3 H3 107.2
C2 C3 H3 107.2
C5 C4 C3 124.86(15)
C5 C4 H4 117.6
C3 C4 H4 117.6
C4 C5 C6 123.92(14)
C4 C5 H5 118.0
C6 C5 H5 118.0
C5 C6 C7 111.22(13)
C5 C6 H6A 109.4
C7 C6 H6A 109.4
C5 C6 H6B 109.4
C7 C6 H6B 109.4
H6A C6 H6B 108.0
N1 C7 C6 111.82(13)
N1 C7 H7A 109.3
C6 C7 H7A 109.3
N1 C7 H7B 109.3
C6 C7 H7B 109.3
H7A C7 H7B 107.9
O2 C8 N1 124.82(14)
O2 C8 O1 123.67(14)
N1 C8 O1 111.49(12)
O1 C9 C10 112.80(12)
O1 C9 H9A 109.0
C10 C9 H9A 109.0
O1 C9 H9B 109.0
C10 C9 H9B 109.0
H9A C9 H9B 107.8
C11 C10 C15 118.83(15)
C11 C10 C9 118.87(14)
C15 C10 C9 122.22(15)
C12 C11 C10 120.60(16)
C12 C11 H11 119.7
C10 C11 H11 119.7
C11 C12 C13 120.01(17)
C11 C12 H12 120.0
C13 C12 H12 120.0
C14 C13 C12 119.71(17)
C14 C13 H13 120.1
C12 C13 H13 120.1
C13 C14 C15 120.55(17)
C13 C14 H14 119.7
C15 C14 H14 119.7
C14 C15 C10 120.30(17)
C14 C15 H15 119.8
C10 C15 H15 119.8
S1 C16 H16A 109.5
S1 C16 H16B 109.5
H16A C16 H16B 109.5
S1 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O5 1.4222(11)
S1 O4 1.4284(11)
S1 O3 1.5769(11)
S1 C16 1.7465(16)
O1 C8 1.3605(18)
O1 C9 1.4432(19)
O2 C8 1.2179(18)
O3 C2 1.4693(16)
N1 C8 1.3472(19)
N1 C1 1.4553(19)
N1 C7 1.4681(19)
N2 N3 1.237(2)
N2 C3 1.488(2)
N3 N4 1.133(2)
C1 C2 1.532(2)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.541(2)
C2 H2 1.0000
C3 C4 1.513(2)
C3 H3 1.0000
C4 C5 1.330(2)
C4 H4 0.9500
C5 C6 1.485(2)
C5 H5 0.9500
C6 C7 1.527(2)
C6 H6A 0.9900
C6 H6B 0.9900
C7 H7A 0.9900
C7 H7B 0.9900
C9 C10 1.504(2)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.392(2)
C10 C15 1.393(2)
C11 C12 1.386(2)
C11 H11 0.9500
C12 C13 1.386(3)
C12 H12 0.9500
C13 C14 1.378(3)
C13 H13 0.9500
C14 C15 1.384(3)
C14 H14 0.9500
C15 H15 0.9500
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
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
O5 S1 O3 C2 -166.43(10)
O4 S1 O3 C2 -38.02(11)
C16 S1 O3 C2 78.26(11)
C3 N2 N3 N4 -174.6(11)
C8 N1 C1 C2 -78.63(16)
C7 N1 C1 C2 108.08(15)
S1 O3 C2 C1 -119.61(11)
S1 O3 C2 C3 118.59(11)
N1 C1 C2 O3 174.11(11)
N1 C1 C2 C3 -69.82(17)
N3 N2 C3 C4 47.86(19)
N3 N2 C3 C2 -78.21(16)
O3 C2 C3 N2 -47.99(15)
C1 C2 C3 N2 -162.46(12)
O3 C2 C3 C4 -173.76(12)
C1 C2 C3 C4 71.78(17)
N2 C3 C4 C5 150.47(16)
C2 C3 C4 C5 -84.21(19)
C3 C4 C5 C6 5.8(2)
C4 C5 C6 C7 88.90(19)
C8 N1 C7 C6 127.65(15)
C1 N1 C7 C6 -59.61(17)
C5 C6 C7 N1 -49.95(17)
C1 N1 C8 O2 3.7(2)
C7 N1 C8 O2 176.56(14)
C1 N1 C8 O1 -175.12(12)
C7 N1 C8 O1 -2.3(2)
C9 O1 C8 O2 7.8(2)
C9 O1 C8 N1 -173.33(12)
C8 O1 C9 C10 76.99(16)
O1 C9 C10 C11 -164.84(13)
O1 C9 C10 C15 18.5(2)
C15 C10 C11 C12 0.4(2)
C9 C10 C11 C12 -176.44(15)
C10 C11 C12 C13 -0.6(2)
C11 C12 C13 C14 0.2(3)
C12 C13 C14 C15 0.6(3)
C13 C14 C15 C10 -0.8(3)
C11 C10 C15 C14 0.4(2)
C9 C10 C15 C14 177.06(15)
loop_
_reflns_scale_group_code
_reflns_scale_meas_F
1 1.0
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 26050932 ChemSpider
2 52918312 PubChem
