Total synthesis and confirmation of the revised structures of jiangrines A, C and D.
Zhang, Zhijiang; Liu, Bo; Organic & biomolecular chemistry 15 (2016) 207–212; doi:10.1039/c6ob02379g

data_7155376
_publ_section_title
;
 Total synthesis and confirmation of the revised structures of jiangrines
 A, C and D.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              207
_journal_page_last               212
_journal_paper_doi               10.1039/c6ob02379g
_journal_volume                  15
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C14 H21 N O5'
_chemical_formula_sum            'C14 H21 N O5'
_chemical_formula_weight         283.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-10-14
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2016-10-20 deposited with the CCDC.
2016-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4821(4)
_cell_length_b                   13.9447(9)
_cell_length_c                   14.9797(12)
_cell_measurement_reflns_used    1053
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.3850
_cell_measurement_theta_min      3.3710
_cell_volume                     1562.92(18)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -12.00  18.00   1.00   12.50    --  -14.97 -99.00-180.00   30
  2  \w     49.00  78.00   1.00   12.50    --   16.69  57.00-120.00   29
  3  \w      1.00  86.00   1.00   12.50    --   16.69  38.00  30.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0003403000
_diffrn_orient_matrix_UB_12      0.0313283000
_diffrn_orient_matrix_UB_13      0.0372594000
_diffrn_orient_matrix_UB_21      -0.0051638000
_diffrn_orient_matrix_UB_22      0.0400632000
_diffrn_orient_matrix_UB_23      -0.0290991000
_diffrn_orient_matrix_UB_31      -0.0946774000
_diffrn_orient_matrix_UB_32      -0.0021139000
_diffrn_orient_matrix_UB_33      0.0017131000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4877
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         3.043
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 637 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2994
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0523
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0553P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1210
_reflns_Friedel_coverage         0.621
_reflns_Friedel_fraction_full    0.866
_reflns_Friedel_fraction_max     0.850
_reflns_number_gt                2172
_reflns_number_total             2994
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob02379g2.cif
_cod_data_source_block           161013_s2_zkj
_cod_depositor_comments          'Adding full bibliography for 7155376.cif.'
_cod_database_code               7155376
_chemical_oxdiff_formula         c12h12n2o3
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.964
_reflns_odcompleteness_completeness 99.68
_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 C(H,H,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(O4) = Uanis(O4A)
Uanis(O5) = Uanis(O5A)
3. Others
 Sof(H9B)=Sof(H10C)=Sof(H10D)=Sof(O4A)=Sof(O5A)=1-FVAR(1)
 Sof(H9A)=Sof(H10A)=Sof(H10B)=Sof(O4)=Sof(O5)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9A), C9(H9B)
4.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C10(H10A,H10B), C10(H10C,H10D)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4)
4.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              6618
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.277
_oxdiff_exptl_absorpt_empirical_full_min 0.674