Natalamycin A, an Ansamycin from a Termite-Associated Streptomyces sp.
Kim, Ki Hyun; Ramadhar, Timothy R.; Beemelmanns, Christine; Cao, Shugeng; Poulsen, Michael; Currie, Cameron R.; Clardy, Jon; Chemical science (Royal Society of Chemistry : 2010) 5 (2014) 4333–4338; doi:10.1039/C4SC01136H

data_1517165
_publ_section_title
;
 Natalamycin A, an Ansamycin from a Termite-Associated Streptomyces sp.
;
_journal_issue                   11
_journal_name_full
'Chemical science (Royal Society of Chemistry : 2010)'
_journal_page_first              4333
_journal_page_last               4338
_journal_paper_doi               10.1039/C4SC01136H
_journal_volume                  5
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C35 H50 N2 O11, 3(C H Cl3)'
_chemical_formula_sum            'C38 H53 Cl9 N2 O11'
_chemical_formula_weight         1032.87
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-03-06
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9360(18)
_cell_length_b                   17.448(2)
_cell_length_c                   21.111(3)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    15(2)
_cell_measurement_theta_max      15.79
_cell_measurement_theta_min      2.74
_cell_volume                     4764.9(11)
_computing_cell_refinement       'SAINT 8.30A (Bruker-AXS, 2012)'
_computing_data_collection       'APEX2 v2013.4.1 (Bruker-AXS, 2013)'
_computing_data_reduction        'SAINT 8.30A (Bruker-AXS, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      15.0
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device       'three-circle goniometer with fixed chi'
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'Si 1 1 1'
_diffrn_radiation_source         synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.41328
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.940
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            33421
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        14.357
_diffrn_reflns_theta_max         15.787
_diffrn_reflns_theta_min         0.880
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_T_max  0.8503
_exptl_absorpt_correction_T_min  0.6576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1423 before and 0.0567 after correction. The Ratio of minimum to maximum transmission is 0.7734. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_description       block
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.834
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.173
_refine_ls_abs_structure_details
;
Data was collected using synchrotron radiation (0.41325 nm). The Flack x determined using 4671 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, 2004) was considered to be unreliable for chirality determination.

The absolute stereochemistry was confirmed using Bayesian statistics on 4731 select Bijvoet pairs (Hooft, Straver & Spek, 2008) using the ByvoetPair tool in PLATON version 251013 (Spek, 2009). The Hooft y parameter was determined to be 0.00(4).
;
_refine_ls_abs_structure_Flack   0.12(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     553
_refine_ls_number_reflns         10598
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0635
_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/[\s^2^(Fo^2^)+(0.0584P)^2^+39.2026P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1840
_refine_ls_wR_factor_ref         0.1913
_reflns_Friedel_coverage         0.806
_reflns_Friedel_fraction_full    0.946
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                10533
_reflns_number_total             10598
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4sc01136h3.cif
_cod_data_source_block           kt29-076res_a
_cod_depositor_comments
;Adding full bibliography for 1517165.cif.

 Adding full bibliography for 1517165.cif.
;
_cod_database_code               1517165
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.863
_shelx_estimated_absorpt_t_min   0.827
_refine_ls_abs_structure_hooft   0.00(4)
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O7) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.2
3.a Rotating group:
 N2(H2A,H2B)
3.b Ternary CH refined with riding coordinates:
 C8(H8), C12(H12), C20(H20), C22(H22), C27(H27), C29(H29), C30(H30), C33(H33),
 C36(H36), C38(H38), C37(H37)
3.c Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C32(H32A,H32B), C35(H35A,H35B)
3.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C17(H17), C18(H18), C19(H19), C26(H26)
3.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C13(H13A,H13B,H13C), C16(H16A,H16B,H16C),
 C21(H21A,H21B,H21C), C25(H25A,H25B,H25C), C28(H28A,H28B,H28C), C31(H31A,H31B,
 H31C), C34(H34A,H34B,H34C)
3.f Idealised tetrahedral OH refined as rotating group:
 O1(H1), O10(H10)
;
_shelx_res_checksum              15976
_shelx_hkl_checksum              76883
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'