Chlorinated metabolites from Streptomyces sp. highlight the role of biosynthetic mosaics and superclusters in the evolution of chemical diversity.
Morshed, Mahmud T.; Lacey, Ernest; Vuong, Daniel; Lacey, Alastair E.; Lean, Soo Sum; Moggach, Stephen A.; Karuso, Peter; Chooi, Yit-Heng; Booth, Thomas J.; Piggott, Andrew M.; Organic & biomolecular chemistry 19 (2021) 6147–6159; doi:10.1039/d1ob00600b

data_7158133
_publ_section_title
;
 Chlorinated metabolites from Streptomyces sp. highlight the role of
 biosynthetic mosaics and superclusters in the evolution of chemical
 diversity.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6147
_journal_page_last               6159
_journal_paper_doi               10.1039/d1ob00600b
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H35 Cl N8 O10'
_chemical_formula_sum            'C24 H35 Cl N8 O10'
_chemical_formula_weight         631.05
_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_date             2021-05-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-06-01 deposited with the CCDC.	2021-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.73870(10)
_cell_length_b                   9.58890(10)
_cell_length_c                   44.6727(4)
_cell_measurement_reflns_used    22921
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.1390
_cell_measurement_theta_min      3.9350
_cell_volume                     2886.60(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     31.00 119.00   0.50    0.05    --   46.07  57.00  90.00  176
  2  \w     89.00 174.00   0.50    0.25    --  102.29  50.00  -2.00  170
  3  \w     80.00 174.00   0.50    0.25    --  102.29  77.00 -60.00  188
  4  \w     33.00 119.00   0.50    0.05    --   46.07  50.00  -2.00  172
  5  \w     90.00 174.00   0.50    0.25    --  102.29  45.00  90.00  168
  6  \w     90.00 176.00   0.50    0.25    --  102.29  30.00  60.00  172
  7  \w     89.00 177.00   0.50    0.25    --  102.29  15.00  60.00  176
  8  \w     89.00 177.00   0.50    0.25    --  102.29  15.00 -60.00  176
  9  \w    -71.00 -30.00   0.50    0.25    -- -102.29  61.00-150.00   82
 10  \w   -111.00 -30.00   0.50    0.25    -- -102.29 125.00-180.00  162
 11  \w   -110.00 -30.00   0.50    0.25    -- -102.29 124.00-132.00  160
 12  \w    -71.00 -30.00   0.50    0.25    -- -102.29  61.00   0.00   82
 13  \w     30.00 110.00   0.50    0.25    --  102.29-124.00 147.00  160
 14  \w    -71.00 -30.00   0.50    0.25    -- -102.29  61.00 150.00   82
 15  \w   -174.00 -90.00   0.50    0.25    -- -102.29 -45.00 150.00  168
 16  \w   -118.00 -31.00   0.50    0.05    --  -46.07 -57.00 120.00  174
 17  \w   -174.00-100.00   0.50    0.25    -- -102.29 -61.00 -90.00  148
 18  \w   -174.00 -90.00   0.50    0.25    -- -102.29 -45.00-120.00  168
 19  \w   -174.00 -89.00   0.50    0.25    -- -102.29 -50.00-149.00  170
 20  \w   -174.00 -90.00   0.50    0.25    -- -102.29 -45.00-180.00  168
 21  \w   -118.00 -33.00   0.50    0.05    --  -46.07 -50.00-149.00  170
 22  \w    -28.00  26.00   0.50    0.05    --   46.07 -19.00  60.00  108
 23  \w    -28.00  26.00   0.50    0.05    --   46.07 -19.00  30.00  108
 24  \w     74.00 119.00   0.50    0.05    --   46.07 125.00 -90.00   90
 25  \w     74.00 119.00   0.50    0.05    --   46.07 125.00 120.00   90
 26  \w     30.00  57.00   0.50    0.25    --  102.29 -50.00-149.00   54
 27  \w     30.00  71.00   0.50    0.25    --  102.29 -61.00-180.00   82
 28  \w     30.00 105.00   0.50    0.25    --  102.29 -77.00 -60.00  150
 29  \w     30.00  71.00   0.50    0.25    --  102.29 -61.00  60.00   82
 30  \w     30.00  71.00   0.50    0.25    --  102.29 -61.00 150.00   82
 31  \w     30.00  89.00   0.50    0.25    --  102.29 -71.00  28.00  118
 32  \w     30.00  71.00   0.50    0.25    --  102.29 -61.00  30.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0345863000
_diffrn_orient_matrix_UB_12      0.0087457000
_diffrn_orient_matrix_UB_13      0.0340441000
_diffrn_orient_matrix_UB_21      0.1357264000
_diffrn_orient_matrix_UB_22      -0.1274385000
_diffrn_orient_matrix_UB_23      0.0046366000
_diffrn_orient_matrix_UB_31      0.1807391000
_diffrn_orient_matrix_UB_32      0.0973324000
_diffrn_orient_matrix_UB_33      0.0030394000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       55
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_number            44662
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.702
_diffrn_reflns_theta_min         3.958
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.780
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.844
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 2272 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         5890
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0334
_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/[\s^2^(Fo^2^)+(0.0387P)^2^+1.0559P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0838
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                5663
_reflns_number_total             5890
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00600b2.cif
_cod_data_source_block           svet02_auto
_cod_depositor_comments          'Adding full bibliography for 7158133.cif.'
_cod_database_code               7158133
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'O6 N8 C50 H40'
_chemical_oxdiff_usercomment     'SvetamycinA Chloride'
_shelx_estimated_absorpt_t_max   0.916
_shelx_estimated_absorpt_t_min   0.764
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 N6A(H6A), N6B(H6B)
2.b Ternary CH refined with riding coordinates:
 C2C(H2C), C2B(H2B), C4D(H4D), C2D(H2DA), C2A(H2A), C3D(H3DA), C4B(H4B)
2.c Secondary CH2 refined with riding coordinates:
 C2E(H2EA,H2EB), C5B(H5BA,H5BB), C3(H3A,H3B), C3B(H3BA,H3BB), C4A(H4AA,H4AB),
 C3A(H3AA,H3AB), C5A(H5AA,H5AB)
2.d Aromatic/amide H refined with riding coordinates:
 N4C(H4C), N5(H5), C5D(H5D)
2.e Idealised Me refined as rotating group:
 C3C(H3CA,H3CB,H3CC), C4(H4A,H4E,H4F)
2.f Idealised tetrahedral OH refined as rotating group:
 O2D(H2D), O3D(H3D), O2(H2)
;
_shelx_res_checksum              23463
_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 1.214
_oxdiff_exptl_absorpt_empirical_full_min 0.801