Synthetic progress toward the marine natural product zamamiphidin A
Wang, Hao; Tian, Di; Meng, Zhaoxiang; Chen, Zhihao; Xue, Fei; Liu, Xiao-Yu; Song, Hao; Qin, Yong; RSC Advances 10 (2020) 11903–11906; doi:10.1039/D0RA01580F

data_7240191
_publ_section_title
;
 Synthetic progress toward the marine natural product zamamiphidin A
;
_journal_issue                   20
_journal_name_full               'RSC Advances'
_journal_page_first              11903
_journal_page_last               11906
_journal_paper_doi               10.1039/D0RA01580F
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C18 H26 N2 O8'
_chemical_formula_sum            'C18 H26 N2 O8'
_chemical_formula_weight         398.41
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-12-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-12-27 deposited with the CCDC.	2020-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.155(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.4436(6)
_cell_length_b                   9.3899(6)
_cell_length_c                   11.6167(8)
_cell_measurement_reflns_used    1031
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.1180
_cell_measurement_theta_min      4.0710
_cell_volume                     1029.90(12)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   -2.00   85.50   0.7000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   38.0000  -30.0000 125

  2 omega  -52.00   21.50   0.7000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -38.0000 -180.0000 105

  3 omega   -7.00   22.40   0.7000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   77.0000 -120.0000 42

  4 omega  -50.00  -22.00   0.7000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -77.0000 -180.0000 40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0750065000
_diffrn_orient_matrix_UB_12      -0.0020141000
_diffrn_orient_matrix_UB_13      -0.0039848000
_diffrn_orient_matrix_UB_21      0.0031203000
_diffrn_orient_matrix_UB_22      0.0076257000
_diffrn_orient_matrix_UB_23      -0.0606441000
_diffrn_orient_matrix_UB_31      0.0023710000
_diffrn_orient_matrix_UB_32      -0.0751354000
_diffrn_orient_matrix_UB_33      -0.0060661000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4893
_diffrn_reflns_point_group_measured_fraction_full 0.842
_diffrn_reflns_point_group_measured_fraction_max 0.825
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         3.060
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83553
_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    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 736 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3483
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0457P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1109
_reflns_Friedel_coverage         0.556
_reflns_Friedel_fraction_full    0.665
_reflns_Friedel_fraction_max     0.629
_reflns_number_gt                2581
_reflns_number_total             3483
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra01580f2.cif
_cod_data_source_block           171215_s3_wh
_cod_depositor_comments          'Adding full bibliography for 7240191.cif.'
_cod_original_cell_volume        1029.89(12)
_cod_database_code               7240191
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.965
_reflns_odcompleteness_completeness 99.64
_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
2. Uiso/Uaniso restraints and constraints
Uanis(C18) = Uanis(C18A)
Uanis(C14) = Uanis(C14A)
Uanis(C13) = Uanis(C13A)
Uanis(O8) = Uanis(O8A)
3. Others
 Sof(C18A)=Sof(H18D)=Sof(H18E)=Sof(H18F)=1-FVAR(1)
 Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(H18C)=FVAR(1)
 Sof(C14A)=Sof(H14D)=Sof(H14E)=Sof(H14F)=1-FVAR(2)
 Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=FVAR(2)
 Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(H13F)=1-FVAR(3)
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=FVAR(3)
 Sof(O8A)=1-FVAR(4)
 Sof(O8)=FVAR(4)
4.a Ternary CH refined with riding coordinates:
 C1(H1A), C4(H4), C7(H7), C9(H9)
4.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1)
4.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C16(H16A,H16B,H16C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C), C18(H18A,H18B,H18C), C13A(H13D,H13E,H13F), C14A(H14D,H14E,H14F),
 C18A(H18D,H18E,H18F)
;
_olex2_submission_special_instructions 'No special instructions were received'