#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:46:51 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258126 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240595.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_7240595
loop_
_publ_author_name
'Khan, Imran'
'Zhang, Haibo'
'Liu, Wei'
'Zhang, Liping'
'Peng, Fang'
'Chen, Yuchan'
'Zhang, Qingbo'
'Zhang, Guangtao'
'Zhang, Weimin'
'Zhang, Changsheng'
_publ_section_title
;
 Identification and bioactivity evaluation of secondary metabolites from
 Antarctic-derived Penicillium chrysogenum CCTCC M 2020019
;
_journal_issue                   35
_journal_name_full               'RSC Advances'
_journal_page_first              20738
_journal_page_last               20744
_journal_paper_doi               10.1039/D0RA03529G
_journal_volume                  10
_journal_year                    2020
_chemical_compound_source        'Penicillium chrysogenum CCTCC M 2020019'
_chemical_formula_moiety         'C2 H6 O S, C9 H6 N O'
_chemical_formula_sum            'C11 H12 N O2 S'
_chemical_formula_weight         222.28
_chemical_name_systematic        'Xanthocillin X'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-29 deposited with the CCDC.	2020-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                96.434(3)
_cell_angle_beta                 102.426(4)
_cell_angle_gamma                94.819(3)
_cell_formula_units_Z            2
_cell_length_a                   6.4707(3)
_cell_length_b                   6.4978(2)
_cell_length_c                   13.6439(5)
_cell_measurement_reflns_used    3518
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      73.8230
_cell_measurement_theta_min      6.9200
_cell_volume                     553.23(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(5)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  30.00   0.50    0.50    --    0.00 -82.00 120.00  116
  2  ω    -19.00   8.00   0.50    0.50    --    0.00 -82.00 -90.00   54
  3  ω    -46.00 -12.00   0.50    0.50    --    0.00 -77.00-180.00   68
  4  ω    -45.00   7.00   0.50    0.50    --    0.00 -77.00  30.00  104
  5  ω    -24.00  11.00   0.50    0.50    --    0.00 -82.00-120.00   70
  6  ω     55.00 122.00   0.50    0.50    --   95.20 -77.00 -30.00  134
  7  ω      6.00 109.00   0.50    0.50    --   95.20 -15.00  90.00  206
  8  ω      6.00 116.00   0.50    0.50    --   95.20 -61.00-120.00  220
  9  ω     24.00 123.00   0.50    0.50    --   95.20 -82.00-120.00  198
 10  ω    152.00 185.00   0.50    0.50    --   95.20  30.00  60.00   66
 11  ω     67.00 102.00   0.50    0.50    --   95.20 -82.00 150.00   70
 12  ω     22.00  82.00   0.50    0.50    --   95.20 -82.00  30.00  120
 13  ω     91.00 126.00   0.50    0.50    --   95.20 -82.00  30.00   70
 14  ω     44.00  71.00   0.50    0.50    --   95.20 -82.00-180.00   54
 15  ω     80.00 127.00   0.50    0.50    --   95.20  77.00  60.00   94
 16  ω     31.00  73.00   0.50    0.50    --   95.20 -61.00  90.00   84
 17  ω     80.00 138.00   0.50    0.50    --   95.20  30.00  60.00  116
 18  ω      6.00 112.00   0.50    0.50    --   95.20 -82.00  90.00  212
 19  ω     72.00 156.00   0.50    0.50    --   95.20  15.00   0.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2250881000
_diffrn_orient_matrix_UB_12      0.0838599000
_diffrn_orient_matrix_UB_13      -0.0075991000
_diffrn_orient_matrix_UB_21      0.0667553000
_diffrn_orient_matrix_UB_22      0.0494296000
_diffrn_orient_matrix_UB_23      0.1162551000
_diffrn_orient_matrix_UB_31      0.0711404000
_diffrn_orient_matrix_UB_32      -0.2194679000
_diffrn_orient_matrix_UB_33      0.0062108000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4537
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.078
_diffrn_reflns_theta_min         6.705
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.439
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear brownish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       block
_exptl_crystal_F_000             234
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DMSO'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2136
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1041P)²+0.0820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1367
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2030
_reflns_number_total             2136
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra03529g2.cif
_cod_data_source_block           zhanghaibo_zys6-5_collect
_cod_depositor_comments
'Adding full bibliography for 7240595--7240596.cif.'
_cod_database_code               7240595
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C22 H24 Cl2 N2 O4 '
_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.
;
_reflns_odcompleteness_completeness 99.25
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C7(H7), C6(H6), C10(H10), C9(H9)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C)
2.c Idealised tetrahedral OH refined as rotating group:
 O11(H11)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.008
_oxdiff_exptl_absorpt_empirical_full_min 0.581
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.71052(5) 0.60003(5) 0.38138(3) 0.0207(2) Uani 1 1 d . . . . .
O11 O 0.59733(17) 0.02556(18) 0.29706(9) 0.0227(3) Uani 1 1 d . . . . .
H11 H 0.632119 0.146385 0.324031 0.034 Uiso 1 1 calc GR . . . .
O1 O 0.73841(19) 0.38577(17) 0.41363(9) 0.0255(3) Uani 1 1 d . . . . .
N14 N -0.37490(19) 0.2407(2) 0.07955(10) 0.0178(3) Uani 1 1 d . . . . .
C8 C -0.0270(2) -0.0461(2) 0.12305(11) 0.0169(3) Uani 1 1 d . . . . .
C12 C -0.2394(2) -0.0891(2) 0.05725(11) 0.0173(3) Uani 1 1 d . . . . .
H12 H -0.272349 -0.225199 0.024626 0.021 Uiso 1 1 calc R . . . .
C7 C 0.1036(2) -0.2093(2) 0.12649(12) 0.0179(3) Uani 1 1 d . . . . .
H7 H 0.049362 -0.337782 0.088462 0.021 Uiso 1 1 calc R . . . .
C13 C -0.3966(2) 0.0334(2) 0.03525(11) 0.0162(3) Uani 1 1 d . . . . .
C5 C 0.3939(2) 0.0061(2) 0.24206(12) 0.0182(3) Uani 1 1 d . . . . .
C6 C 0.3091(2) -0.1848(2) 0.18436(12) 0.0191(3) Uani 1 1 d . . . . .
H6 H 0.391094 -0.295696 0.184862 0.023 Uiso 1 1 calc R . . . .
C10 C 0.2680(2) 0.1711(2) 0.24002(12) 0.0206(4) Uani 1 1 d . . . . .
H10 H 0.323207 0.299331 0.278053 0.025 Uiso 1 1 calc R . . . .
C9 C 0.0620(3) 0.1447(3) 0.18183(12) 0.0217(4) Uani 1 1 d . . . . .
H9 H -0.019497 0.255940 0.181633 0.026 Uiso 1 1 calc R . . . .
C3 C 0.9575(3) 0.6895(3) 0.35391(13) 0.0246(4) Uani 1 1 d . . . . .
H3A H 1.071609 0.682988 0.411149 0.037 Uiso 1 1 calc GR . . . .
H3B H 0.954702 0.830824 0.339794 0.037 Uiso 1 1 calc GR . . . .
H3C H 0.979002 0.602832 0.296002 0.037 Uiso 1 1 calc GR . . . .
C4 C 0.7342(3) 0.7692(3) 0.49687(13) 0.0284(4) Uani 1 1 d . . . . .
H4A H 0.612509 0.738322 0.524533 0.043 Uiso 1 1 calc GR . . . .
H4B H 0.741759 0.911405 0.483701 0.043 Uiso 1 1 calc GR . . . .
H4C H 0.861215 0.748822 0.544420 0.043 Uiso 1 1 calc GR . . . .
C15 C -0.3662(3) 0.4121(3) 0.11625(14) 0.0257(4) Uani 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S2 C3 105.66(7) . . ?
O1 S2 C4 104.76(8) . . ?
C3 S2 C4 98.06(9) . . ?
C5 O11 H11 109.5 . . ?
C15 N14 C13 177.03(15) . . ?
C7 C8 C12 117.18(13) . . ?
C9 C8 C12 126.05(14) . . ?
C9 C8 C7 116.75(14) . . ?
C8 C12 H12 114.3 . . ?
C13 C12 C8 131.42(14) . . ?
C13 C12 H12 114.3 . . ?
C8 C7 H7 118.9 . . ?
C6 C7 C8 122.18(14) . . ?
C6 C7 H7 118.9 . . ?
N14 C13 C13 113.57(15) . 2_455 ?
C12 C13 N14 121.60(13) . . ?
C12 C13 C13 124.83(17) . 2_455 ?
O11 C5 C6 118.45(13) . . ?
O11 C5 C10 122.48(14) . . ?
C6 C5 C10 119.07(14) . . ?
C7 C6 C5 120.00(14) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C5 C10 H10 119.8 . . ?
C9 C10 C5 120.44(15) . . ?
C9 C10 H10 119.8 . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.55(14) . . ?
C10 C9 H9 119.2 . . ?
S2 C3 H3A 109.5 . . ?
S2 C3 H3B 109.5 . . ?
S2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
S2 C4 H4A 109.5 . . ?
S2 C4 H4B 109.5 . . ?
S2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
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
S2 O1 1.5198(11) . ?
S2 C3 1.7839(17) . ?
S2 C4 1.7874(18) . ?
O11 H11 0.8200 . ?
O11 C5 1.3557(19) . ?
N14 C13 1.3958(19) . ?
N14 C15 1.161(2) . ?
C8 C12 1.457(2) . ?
C8 C7 1.409(2) . ?
C8 C9 1.403(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.348(2) . ?
C7 H7 0.9300 . ?
C7 C6 1.379(2) . ?
C13 C13 1.469(3) 2_455 ?
C5 C6 1.393(2) . ?
C5 C10 1.399(2) . ?
C6 H6 0.9300 . ?
C10 H10 0.9300 . ?
C10 C9 1.383(2) . ?
C9 H9 0.9300 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 C5 C6 C7 -179.18(14) . . . . ?
O11 C5 C10 C9 179.23(14) . . . . ?
C8 C12 C13 N14 -1.4(3) . . . . ?
C8 C12 C13 C13 178.73(16) . . . 2_455 ?
C8 C7 C6 C5 0.1(2) . . . . ?
C12 C8 C7 C6 178.53(14) . . . . ?
C12 C8 C9 C10 -178.30(15) . . . . ?
C7 C8 C12 C13 -177.65(15) . . . . ?
C7 C8 C9 C10 0.2(2) . . . . ?
C5 C10 C9 C8 -0.3(3) . . . . ?
C6 C5 C10 C9 0.2(2) . . . . ?
C10 C5 C6 C7 -0.2(2) . . . . ?
C9 C8 C12 C13 0.8(3) . . . . ?
C9 C8 C7 C6 -0.1(2) . . . . ?
