Total synthesis and structure revision of chrysamide B
Chen, Jinhong; Li, Junfang; Zhu, Longqing; Peng, Xue; Feng, Yiyue; Lu, Yingmei; Hu, Xiaoling; Liang, Jianpin; Zhao, Quanyi; Wang, Zhen; Organic Chemistry Frontiers 5 (2018) 3402–; doi:10.1039/C8QO00949J

data_1554470
_publ_section_title
;
 Total synthesis and structure revision of chrysamide B
;
_journal_issue                   23
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3402
_journal_paper_doi               10.1039/C8QO00949J
_journal_volume                  5
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C26 H28 N4 O8, H2 O'
_chemical_formula_sum            'C26 H30 N4 O9'
_chemical_formula_weight         542.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-04-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-04-02 deposited with the CCDC.
2018-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.162(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.9349(9)
_cell_length_b                   5.4755(5)
_cell_length_c                   25.351(3)
_cell_measurement_reflns_used    1252
_cell_measurement_temperature    292.9(8)
_cell_measurement_theta_max      26.9690
_cell_measurement_theta_min      4.1770
_cell_volume                     1353.0(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.9(8)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details
;
  1 omega  -43.00   47.00   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -38.0000   30.0000 60

  2 omega   -5.00   25.00   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492  -99.0000   60.0000 20

  3 omega  -20.00   59.50   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000   30.0000 53

  4 omega  -48.00   45.00   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000  150.0000 62

  5 omega   -1.00   51.50   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  -60.0000 35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0090800000
_diffrn_orient_matrix_UB_12      -0.0906687000
_diffrn_orient_matrix_UB_13      -0.0203779000
_diffrn_orient_matrix_UB_21      0.0200442000
_diffrn_orient_matrix_UB_22      -0.0913564000
_diffrn_orient_matrix_UB_23      0.0198012000
_diffrn_orient_matrix_UB_31      -0.0693616000
_diffrn_orient_matrix_UB_32      -0.0145578000
_diffrn_orient_matrix_UB_33      0.0026031000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            3928
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.52
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.0(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2177
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0379P)^2^+0.6330P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1064
_reflns_number_gt                1814
_reflns_number_total             2177
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8qo00949j2.cif
_cod_data_source_block           wangzh_0327
_cod_original_cell_volume        1352.9(2)
_cod_database_code               1554470
_reflns_odcompleteness_completeness 95.44
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C13(H13A,H13B,H13C)
;
_olex2_date_sample_data_collection 2018-03-27
_olex2_submission_special_instructions 'No special instructions were received'