Total Synthesis of Nannocystin Ax
Zhang, Yanhui; Liu, Rong; Liu, Bo; Chem. Commun.  (2017) –; doi:10.1039/C7CC00469A

data_7119989
_publ_section_title
;
 Total Synthesis of Nannocystin Ax
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC00469A
_journal_year                    2017
_chemical_formula_moiety         'C42 H55 Cl2 N3 O8'
_chemical_formula_sum            'C42 H55 Cl2 N3 O8'
_chemical_formula_weight         800.79
_chemical_name_systematic
;
 ? 
;
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-11-29
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.24 svn.r3356 for OlexSys, GUI svn.r5267)
;
_audit_update_record
;
2016-11-29 deposited with the CCDC.
2017-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.966(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.4214(10)
_cell_length_b                   11.6137(6)
_cell_length_c                   16.9862(11)
_cell_measurement_reflns_used    2221
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.0790
_cell_measurement_theta_min      3.5090
_cell_volume                     2638.4(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.5965
_diffrn_measurement_details
;
  1 omega   -9.00   17.40   0.8000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  -90.0000 33

  2 omega   -1.00   83.00   0.8000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   38.0000  120.0000 105

  3 omega   44.00   80.00   0.8000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   57.0000 -150.0000 45

  4 omega    7.00   73.40   0.8000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   57.0000    0.0000 83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0530130000
_diffrn_orient_matrix_UB_12      -0.0010774000
_diffrn_orient_matrix_UB_13      0.0159487000
_diffrn_orient_matrix_UB_21      -0.0010507000
_diffrn_orient_matrix_UB_22      0.0057877000
_diffrn_orient_matrix_UB_23      -0.0419001000
_diffrn_orient_matrix_UB_31      0.0010607000
_diffrn_orient_matrix_UB_32      0.0607841000
_diffrn_orient_matrix_UB_33      0.0042672000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12198
_diffrn_reflns_point_group_measured_fraction_full 0.741
_diffrn_reflns_point_group_measured_fraction_max 0.721
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.923
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.008
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1321 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     521
_refine_ls_number_reflns         7779
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.929
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0587
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1065P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1578
_refine_ls_wR_factor_ref         0.1729
_reflns_Friedel_coverage         0.374
_reflns_Friedel_fraction_full    0.456
_reflns_Friedel_fraction_max     0.414
_reflns_number_gt                4664
_reflns_number_total             7779
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc00469a2.cif
_cod_data_source_block           161128_s3_zyh
_cod_database_code               7119989
_chemical_oxdiff_formula         c12h12n2o3
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.944
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Restrained distances
 C23-Cl2A = C21-Cl1A
 1.8 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Cl1) = Uanis(Cl1A)
Uanis(Cl2) = Uanis(Cl2A)
Uanis(O3) = Uanis(O3A)
4. Others
 Sof(Cl1A)=Sof(Cl2A)=Sof(O3A)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(O3)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C1(H1B), C3(H3), C5(H5), C6(H6), C11(H11), C16(H16), C39(H39)
5.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C18(H18A,H18B), C41(H41A,H41B)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), C7(H7), C8(H8), C9(H9), C13(H13), C20(H20), C24(H24), C29(H29),
 C30(H30), C31(H31), C32(H32), C33(H33)
5.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C34(H34A,H34B,H34C), C35(H35A,H35B,
 H35C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C40(H40A,
 H40B,H40C), C42(H42A,H42B,H42C)
5.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'