Dudawalamides A-D, Antiparasitic Cyclic Depsipeptides from the Marine Cyanobacterium Moorea producens.
Almaliti, Jehad; Malloy, Karla L.; Glukhov, Evgenia; Spadafora, Carmenza; Gutiérrez, Marcelino; Gerwick, William H.; Journal of natural products 80 (2017) 1827–1836; doi:10.1021/acs.jnatprod.7b00034

data_1553307
_publ_section_title
;
 Dudawalamides A-D, Antiparasitic Cyclic Depsipeptides from the Marine
 Cyanobacterium Moorea producens.
;
_journal_issue                   6
_journal_name_full               'Journal of natural products'
_journal_page_first              1827
_journal_page_last               1836
_journal_paper_doi               10.1021/acs.jnatprod.7b00034
_journal_volume                  80
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C42 H69 N5 O10, 0.25(H2 O), 0.75(C3 H6 O)'
_chemical_formula_sum            'C44.25 H74 N5 O11'
_chemical_formula_weight         852.08
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-05-08
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.794(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.6436(5)
_cell_length_b                   10.5780(4)
_cell_length_c                   15.5742(7)
_cell_measurement_reflns_used    9347
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.052
_cell_measurement_theta_min      5.689
_cell_volume                     2409.58(16)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2016.9-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 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_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            42468
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         70.564
_diffrn_reflns_theta_min         3.021
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker Microstar FR-592'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.684
_exptl_absorpt_correction_T_max  0.2240
_exptl_absorpt_correction_T_min  0.1186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0908 before and 0.0645 after correction. The Ratio of minimum to maximum transmission is 0.5295. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_description       Plate
_exptl_crystal_F_000             925
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 3710 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     572
_refine_ls_number_reflns         8830
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0685
_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^)+(0.0962P)^2^+2.8752P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1919
_refine_ls_wR_factor_ref         0.1926
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_full    0.959
_reflns_Friedel_fraction_max     0.931
_reflns_number_gt                8662
_reflns_number_total             8830
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00034_si_002.cif
_cod_data_source_block           Gerw15
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               1553307
_shelx_shelxl_version_number     2016/6
_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, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O1SC) = Uanis(O1S) = Uanis(O1SB)
3. Others
 Fixed Sof: O1SB(0.125) H1SD(0.125) H1SE(0.125) O1S(0.75) C1S(0.75) H1SA(0.75)
 H1SB(0.75) H1SC(0.75) C2S(0.75) C3S(0.75) H3SA(0.75) H3SB(0.75) H3SC(0.75)
 O1SC(0.125) H1SF(0.125) H1SG(0.125)
 Fixed X: H1SD(0.407749) H1SE(0.45326) H1SF(0.54365) H1SG(0.48136)
 Fixed Y: H1SD(0.57562) H1SE(0.48895) H1SF(0.44325) H1SG(0.46142)
 Fixed Z: H1SD(0.01537) H1SE(-0.037571) H1SF(-0.148879) H1SG(-0.08288)
4.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3A), C6(H6), C7(H7), C12(H12), C17(H17), C18(H18), C23(H23),
 C24(H24), C29(H29), C30(H30), C37(H37)
4.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C20(H20A,H20B), C38(H38A,
 H38B), C39(H39A,H39B), C40(H40A,H40B)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N5(H5)
4.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C),
 C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C35(H35A,
 H35B,H35C), C36(H36A,H36B,H36C), C1S(H1SA,H1SB,H1SC), C3S(H3SA,H3SB,H3SC)
4.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
4.f :
 C42(H42)
;
_shelx_res_checksum              28286
_shelx_hkl_checksum              2017
_olex2_submission_special_instructions 'No special instructions were received'