#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/05/7150548.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_7150548
loop_
_publ_author_name
'Kaiser, Jasper'
'van Esseveldt, Bart C. J.'
'Segers, Margot J. A.'
'van Delft, Floris L.'
'Smits, Jan M. M.'
'Butterworth, Sam'
'Rutjes, Floris P. J. T.'
_publ_section_title
;
 Synthesis and aromatisation of cyclic enediyne-containing amino acids
;
_journal_issue                   4
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              695
_journal_page_last               705
_journal_paper_doi               10.1039/b815176h
_journal_volume                  7
_journal_year                    2009
_chemical_formula_sum            'C24 H23 N O4 S'
_chemical_formula_weight         421.49
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2006-07-27
_audit_creation_method           'SHELXL, adapted and expanded'
_cell_angle_alpha                69.128(6)
_cell_angle_beta                 70.351(5)
_cell_angle_gamma                84.942(5)
_cell_formula_units_Z            2
_cell_length_a                   8.4021(5)
_cell_length_b                   11.9570(9)
_cell_length_c                   12.0405(8)
_cell_measurement_reflns_used    115
_cell_measurement_temperature    208(2)
_cell_measurement_theta_max      27.500
_cell_measurement_theta_min      2.580
_cell_volume                     1063.75(14)
_computing_data_collection
;
Nonius "Collect" program suite (Nonius, 1999)
;
_computing_data_reduction
;
Nonius "EvalCCD" program suite (Duisenberg, 1998)
;
_computing_molecular_graphics
;
PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
DIRDIF (Beurskens et al., 1996),
PATTY (Beurskens et al., 1987)
;
_diffrn_ambient_temperature      208(2)
_diffrn_detector_area_resol_mean 18.4
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       'area detector φ and ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0156
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27752
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.58
_diffrn_standards_decay_%        0.000
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.9422
_exptl_absorpt_correction_T_min  0.8059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS multiscan (Sheldrick, 1996)'
_exptl_crystal_colour            'translucent light yellow'
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rather regular large fragment'
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.083
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4862
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0364
_refine_ls_R_factor_obs          0.0364
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_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)+(0.0407P)²+0.4145P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0967
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_obs         0.0888
_refine_ls_wR_factor_ref         0.0967
_reflns_number_gt                4028
_reflns_number_observed          4028
_reflns_number_total             4862
_reflns_observed_criterion       >2sigma(I)
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b815176h.txt
_cod_data_source_block           JK93
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (44
times).

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (32 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        1063.76(12)
_cod_database_code               7150548
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.09877(4) 0.25211(3) 0.13884(3) 0.02866(10) Uani 1 d . . .
O1 O 1.24894(13) 0.19086(11) 0.15118(10) 0.0399(3) Uani 1 d . . .
O2 O 1.10912(14) 0.36109(10) 0.03673(9) 0.0373(3) Uani 1 d . . .
O3 O 0.78260(12) 0.03935(9) 0.54747(9) 0.0322(2) Uani 1 d . . .
O4 O 0.68950(13) 0.16261(9) 0.39477(10) 0.0341(2) Uani 1 d . . .
N1 N 1.00528(14) 0.28246(10) 0.26634(10) 0.0252(2) Uani 1 d . . .
C1 C 0.90197(17) 0.38908(12) 0.26017(13) 0.0264(3) Uani 1 d . . .
H1A H 0.8128 0.3750 0.3415 0.032 Uiso 1 calc R . .
H1B H 0.8475 0.4023 0.1964 0.032 Uiso 1 calc R . .
C2 C 1.0064(2) 0.49992(13) 0.22802(15) 0.0346(3) Uani 1 d . . .
H2A H 1.0843 0.5211 0.1415 0.041 Uiso 1 calc R . .
H2B H 1.0740 0.4829 0.2841 0.041 Uiso 1 calc R . .
C3 C 0.8951(2) 0.60564(13) 0.24086(15) 0.0431(4) Uani 1 d . . .
H3A H 0.9666 0.6784 0.2074 0.052 Uiso 1 calc R . .
H3B H 0.8195 0.6178 0.1911 0.052 Uiso 1 calc R . .
C4 C 0.7946(2) 0.58548(13) 0.37178(16) 0.0375(3) Uani 1 d . . .
C5 C 0.7219(2) 0.55890(14) 0.48140(16) 0.0359(3) Uani 1 d . . .
C6 C 0.65069(18) 0.51313(15) 0.61537(15) 0.0345(3) Uani 1 d . . .
C7 C 0.5501(2) 0.58094(18) 0.68352(18) 0.0461(4) Uani 1 d . . .
H7 H 0.5240 0.6592 0.6411 0.055 Uiso 1 calc R . .
C8 C 0.4884(2) 0.5338(2) 0.81314(19) 0.0548(5) Uani 1 d . . .
H8 H 0.4223 0.5810 0.8584 0.066 Uiso 1 calc R . .
C9 C 0.5221(2) 0.4190(2) 0.87682(18) 0.0518(5) Uani 1 d . . .
H9 H 0.4776 0.3874 0.9651 0.062 Uiso 1 calc R . .
C10 C 0.6213(2) 0.35031(17) 0.81126(16) 0.0433(4) Uani 1 d . . .
H10 H 0.6442 0.2716 0.8550 0.052 Uiso 1 calc R . .
C11 C 0.68809(19) 0.39649(14) 0.68044(14) 0.0336(3) Uani 1 d . . .
C12 C 0.8007(2) 0.32802(13) 0.61298(14) 0.0333(3) Uani 1 d . . .
C13 C 0.90235(19) 0.27746(13) 0.55392(14) 0.0321(3) Uani 1 d . . .
C14 C 1.02937(18) 0.21572(13) 0.48205(13) 0.0299(3) Uani 1 d . . .
H14A H 1.0555 0.1416 0.5411 0.036 Uiso 1 calc R . .
H14B H 1.1331 0.2663 0.4379 0.036 Uiso 1 calc R . .
C15 C 0.97842(16) 0.18400(11) 0.38487(12) 0.0235(3) Uani 1 d . . .
H15 H 1.0538 0.1201 0.3656 0.028 Uiso 1 calc R . .
C16 C 0.79894(16) 0.13053(11) 0.44036(12) 0.0242(3) Uani 1 d . . .
C17 C 0.6194(2) -0.02297(17) 0.60851(17) 0.0492(5) Uani 1 d . . .
H17A H 0.5315 0.0342 0.6200 0.074 Uiso 1 calc R . .
H17B H 0.6156 -0.0812 0.6898 0.074 Uiso 1 calc R . .
H17C H 0.6016 -0.0637 0.5567 0.074 Uiso 1 calc R . .
C18 C 0.96552(19) 0.14908(13) 0.13500(13) 0.0310(3) Uani 1 d . . .
C19 C 0.9889(2) 0.02748(15) 0.18332(18) 0.0451(4) Uani 1 d . . .
H19 H 1.0802 -0.0002 0.2132 0.054 Uiso 1 calc R . .
C20 C 0.8779(3) -0.05227(17) 0.1873(2) 0.0571(5) Uani 1 d . . .
H20 H 0.8931 -0.1348 0.2213 0.069 Uiso 1 calc R . .
C21 C 0.7436(3) -0.01402(18) 0.14217(18) 0.0519(5) Uani 1 d . . .
C22 C 0.7219(2) 0.10796(18) 0.09467(16) 0.0465(4) Uani 1 d . . .
H22 H 0.6306 0.1355 0.0648 0.056 Uiso 1 calc R . .
C23 C 0.8318(2) 0.19010(15) 0.09029(14) 0.0372(3) Uani 1 d . . .
H23 H 0.8159 0.2727 0.0574 0.045 Uiso 1 calc R . .
C24 C 0.6249(3) -0.1030(2) 0.1450(3) 0.0802(8) Uani 1 d . . .
H24A H 0.5175 -0.0665 0.1438 0.120 Uiso 1 calc R . .
H24B H 0.6073 -0.1727 0.2210 0.120 Uiso 1 calc R . .
H24C H 0.6735 -0.1272 0.0721 0.120 Uiso 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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 120.02(7) . . y
O2 S1 N1 106.24(6) . . y
O1 S1 N1 107.75(6) . . y
O2 S1 C18 108.76(7) . . y
O1 S1 C18 106.46(7) . . y
N1 S1 C18 106.98(6) . . y
C16 O3 C17 115.63(11) . . y
C15 N1 C1 120.31(11) . . y
C15 N1 S1 116.77(9) . . y
C1 N1 S1 119.39(9) . . y
N1 C1 C2 112.02(11) . . y
C1 C2 C3 111.60(13) . . y
C4 C3 C2 111.38(13) . . y
C5 C4 C3 173.33(17) . . y
C4 C5 C6 171.79(17) . . y
C7 C6 C11 118.97(15) . . y
C7 C6 C5 122.49(16) . . y
C11 C6 C5 118.51(14) . . y
C8 C7 C6 120.28(19) . . y
C9 C8 C7 120.84(17) . . y
C8 C9 C10 119.85(17) . . y
C9 C10 C11 120.51(18) . . y
C10 C11 C6 119.53(15) . . y
C10 C11 C12 120.43(15) . . y
C6 C11 C12 119.97(14) . . y
C13 C12 C11 175.42(16) . . y
C12 C13 C14 179.09(15) . . y
C13 C14 C15 115.18(12) . . y
N1 C15 C16 112.24(10) . . y
N1 C15 C14 113.53(11) . . y
C16 C15 C14 111.34(11) . . y
O4 C16 O3 124.51(12) . . y
O4 C16 C15 125.88(12) . . y
O3 C16 C15 109.59(11) . . y
C23 C18 C19 120.41(15) . . y
C23 C18 S1 119.57(12) . . y
C19 C18 S1 119.91(13) . . y
C20 C19 C18 119.47(17) . . y
C19 C20 C21 121.50(18) . . y
C22 C21 C20 118.16(16) . . y
C22 C21 C24 121.1(2) . . y
C20 C21 C24 120.7(2) . . y
C23 C22 C21 121.36(17) . . y
C22 C23 C18 119.08(16) . . y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4225(11) . y
S1 O1 1.4269(11) . y
S1 N1 1.6253(12) . y
S1 C18 1.7583(15) . y
O3 C16 1.3327(16) . y
O3 C17 1.4448(17) . y
O4 C16 1.1921(16) . y
N1 C15 1.4515(16) . y
N1 C1 1.4714(17) . y
C1 C2 1.5122(19) . y
C2 C3 1.526(2) . y
C3 C4 1.458(2) . y
C4 C5 1.187(2) . y
C5 C6 1.428(2) . y
C6 C7 1.390(2) . y
C6 C11 1.403(2) . y
C7 C8 1.379(3) . y
C8 C9 1.371(3) . y
C9 C10 1.375(3) . y
C10 C11 1.393(2) . y
C11 C12 1.430(2) . y
C12 C13 1.187(2) . y
C13 C14 1.459(2) . y
C14 C15 1.5420(18) . y
C15 C16 1.5223(18) . y
C18 C23 1.383(2) . y
C18 C19 1.384(2) . y
C19 C20 1.370(3) . y
C20 C21 1.386(3) . y
C21 C22 1.384(3) . y
C21 C24 1.505(3) . y
C22 C23 1.382(2) . y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25942272
2 PubChem 139190116
