Cyclodepsipeptide Alveolaride C: Total Synthesis and Structural Assignment
Saha, Sanu; Paul, Debobrata; Goswami, Rajib Kumar; Chemical Science  (2020) –; doi:10.1039/D0SC04478D

data_1559135
_publ_section_title
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 Cyclodepsipeptide Alveolaride C: Total Synthesis and Structural
 Assignment
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_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC04478D
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H30 O4'
_chemical_formula_sum            'C15 H30 O4'
_chemical_formula_weight         274.39
_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   geom
_audit_creation_date             2020-03-04
_audit_creation_method
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_audit_update_record
;
2020-03-13 deposited with the CCDC.	2020-09-18 downloaded from the CCDC.
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_cell_angle_alpha                90
_cell_angle_beta                 94.25(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.380(12)
_cell_length_b                   5.067(7)
_cell_length_c                   19.58(3)
_cell_measurement_reflns_used    632
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      24.68
_cell_measurement_theta_min      2.44
_cell_volume                     829(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      301.57
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1653
_diffrn_reflns_av_unetI/netI     0.3293
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4883
_diffrn_reflns_point_group_measured_fraction_full 0.894
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.437
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.3468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1331 before and 0.0768 after correction.
The Ratio of minimum to maximum transmission is 0.4653.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.099
_exptl_crystal_description       needle
_exptl_crystal_F_000             304
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
;
 Flack x determined using 182 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -3.3(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         2666
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.939
_refine_ls_R_factor_all          0.3111
_refine_ls_R_factor_gt           0.1285
_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^)+(0.1380P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2632
_refine_ls_wR_factor_ref         0.3464
_reflns_Friedel_coverage         0.655
_reflns_Friedel_fraction_full    0.808
_reflns_Friedel_fraction_max     0.830
_reflns_number_gt                805
_reflns_number_total             2666
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc04478d2.cif
_cod_data_source_block           test1_a
_cod_database_code               1559135
_shelxl_version_number           2014-3
_olex2_refinement_description
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1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C00D-C009 \\sim C00D-C00C
 with sigma of 0.02
 C00G-C00F \\sim C00H-C00F
 with sigma of 0.02
 C00C-C00A \\sim C00D-C00C
 with sigma of 0.02
 C009-C008 \\sim C00E-C008
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C005) = Uanis(C007)
Uanis(C00A) = Uanis(C00I)
Uanis(C008) = Uanis(C007)
Uanis(C00F) = Uanis(C00H)
4.a Ternary CH refined with riding coordinates:
 C005(H005), C007(H007), C008(H008)
4.b Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B), C00A(H00C,H00D), C00B(H00E,H00F), C00C(H00G,H00H), C00D(H00I,
 H00J), C00F(H00N,H00O), C00G(H00P,H00Q), C00H(H00R,H00S), C00I(H00T,H00U)
4.c Idealised Me refined as rotating group:
 C00E(H00K,H00L,H00M), C00J(H00V,H00W,H00X)
4.d Idealised tetrahedral OH refined as rotating group:
 O001(H001), O002(H002), O004(H004)
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_shelx_res_checksum              52251
_olex2_submission_special_instructions 'No special instructions were received'