Stereoselective total synthesis of marine cyclodepsipeptide calcaripeptides a-C.
Das, Sayantan; Goswami, Rajib Kumar; The Journal of organic chemistry 79 (2014) 9778–9791; doi:10.1021/jo5019798

data_4029975
_publ_section_title
;
 Stereoselective total synthesis of marine cyclodepsipeptide
 calcaripeptides a-C.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9778
_journal_page_last               9791
_journal_paper_doi               10.1021/jo5019798
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C27 H36 N2 O5'
_chemical_formula_sum            'C27 H36 N2 O5'
_chemical_formula_weight          468.58
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-08-22
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                107.633(9)
_cell_angle_beta                 98.257(10)
_cell_angle_gamma                97.712(9)
_cell_formula_units_Z            5
_cell_length_a                   9.6062(14)
_cell_length_b                   18.877(3)
_cell_length_c                   20.063(3)
_cell_measurement_temperature    100(2)
_cell_volume                     3369.8(9)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.941
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_unetI/netI     0.1603
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            50577
_diffrn_reflns_point_group_measured_fraction_full 0.909
_diffrn_reflns_point_group_measured_fraction_max 0.828
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.700
_diffrn_reflns_theta_min         1.086
_exptl_absorpt_coefficient_mu    0.080
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1259
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.034
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 4094 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1551
_refine_ls_number_reflns         26179
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1944
_refine_ls_R_factor_gt           0.0810
_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^)+(0.0917P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1786
_refine_ls_wR_factor_ref         0.2526
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    0.830
_reflns_Friedel_fraction_max     0.714
_reflns_number_gt                11739
_reflns_number_total             26179
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5019798_si_001.cif
_cod_data_source_block           cc_pk_3_sd_aug14_0m_a_new
_cod_depositor_comments          'Adding full bibliography for 4029975.cif.'
_cod_original_cell_volume        3369.9(9)
_cod_database_code               4029975
_shelxl_version_number           2014/6
_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
2.a Ternary CH refined with riding coordinates:
 C00Z(H00Z), C012(H012), C015(H015), C016(H016), C01C(H01C), C01G(H01G),
 C01L(H01L), C01M(H01M), C01O(H01O), C01Q(H01Q), C01S(H01S), C01Z(H01Z),
 C022(H022), C023(H023), C029(H029), C02C(H02D), C02M(H02W), C02P(H7AA),
 C02T(H02T), C02U(H6BA), C02Y(H02), C02Z(H02Z), C032(H032), C03X(H1CA),
 C044(H044)
2.b Secondary CH2 refined with riding coordinates:
 C01U(H01A,H01B), C027(H02N,H02O), C02A(H02A,H02B), C02D(H02P,H02Q), C02E(H3AA,
 H), C02G(H02R,H02S), C02I(H02H,H02I), C02L(H02U,H02V), C02Q(H8AA,HG),
 C02R(H02Y,HH), C02V(H02J,H02K), C02W(H02L,H02M), C030(H03P,H03Q), C033(H03A,
 H03B), C037(H03X,H03Y), C03A(H9AA,HI), C03B(H0BA,HJ), C03C(H1BA,HK), C03G(H3BA,
 HP), C03L(H03K,H03L), C03M(H03R,H03S), C03O(H03,HS), C03P(H8BA,HT), C03R(H9BA,
 HU), C04H(H04J,H04K), C56(H56A,H56B), C55(H55A,H55B), C63(H63A,H63B), C64(H64A,
 H64B)
2.c Aromatic/amide H refined with riding coordinates:
 N12(H12), N13(H13), N14(H14), N00N(H00N), N00R(H00R), C01E(H01E), C01N(H01N),
 C024(H024), C025(H025), C02B(H02C), C02F(H5BA), C02X(H02X), C034(H034),
 C035(H035), C038(H038), C039(H039), C03I(H03I), C03J(H03J), C03N(H03T),
 C03T(H0AA), C03U(H4BA), C03Z(H2AA), C041(H041), C042(H042), C043(H043),
 C046(H046), C04B(H04P), C04C(H04Q), C04G(H04O), C59(H59), C53(H53), C57(H57),
 C58(H58), C62(H62), C60(H60), C61(H61)
2.d Idealised Me refined as rotating group:
 C02H(H02E,H02F,H02G), C02K(H4AA,HA,HB), C02N(H5AA,HC,HD), C02O(H6AA,HE,HF),
 C031(H03U,H03V,H03W), C036(H03C,H03D,H03E), C03D(H03Z,HL,HM), C03E(H2BA,HN,HO),
  C03F(H03F,H03G,H03H), C03H(H7BA,HQ,HR), C03Q(H03M,H03N,H03O), C03V(H1AA,HV,
 HW), C03W(H0CA,HX,HY), C040(H04A,H04B,H04C), C045(H04D,H04E,H04F), C047(H04G,
 H04H,H04I), C049(H04L,H04M,H04N), C04F(H04R,H04S,H04T), C54(H54A,H54B,H54C),
 C65(H65A,H65B,H65C)
;
_shelx_res_checksum              74150
_shelx_hkl_checksum              14829
_olex2_submission_special_instructions 'No special instructions were received'