Taxodikaloids A and B, Two Dimeric Abietane-Type Diterpenoids from Taxodium ascendens Possessing an Oxazoline Ring Linkage.
Huang, Xing-Hao; Tao, Ling-Xue; Ke, Chang-Qiang; Tang, Chunping; Zhang, Hai-Yan; Ye, Yang; Lin, Li-Gen; Yao, Sheng; Organic letters 19 (2017) 556–559; doi:10.1021/acs.orglett.6b03597

data_1545213
_publ_section_title
;
 Taxodikaloids A and B, Two Dimeric Abietane-Type Diterpenoids from
 Taxodium ascendens Possessing an Oxazoline Ring Linkage.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              556
_journal_page_last               559
_journal_paper_doi               10.1021/acs.orglett.6b03597
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C40 H49 N O6'
_chemical_formula_sum            'C40 H49 N O6'
_chemical_formula_weight         639.80
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-21
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.0745(3)
_cell_length_b                   23.3538(7)
_cell_length_c                   5.9816(2)
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    296
_cell_measurement_theta_max      68.05
_cell_measurement_theta_min      3.79
_cell_volume                     1686.72(9)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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
;
????
;
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
scan:
    Number of images: 340
               Slice: -110.0000 - 60.0000
         Image width: 0.5000
            Exp time: 16.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 270.0000
                 XTD: 45.3038
              2theta: -20.1830
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0416
_diffrn_orient_matrix_UB_12      -0.0191
_diffrn_orient_matrix_UB_13      0.0361
_diffrn_orient_matrix_UB_21      0.0301
_diffrn_orient_matrix_UB_22      -0.0492
_diffrn_orient_matrix_UB_23      0.0086
_diffrn_orient_matrix_UB_31      0.0196
_diffrn_orient_matrix_UB_32      0.0176
_diffrn_orient_matrix_UB_33      0.0318
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            23666
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.295
_diffrn_reflns_theta_min         3.785
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  0.1665
_exptl_absorpt_correction_T_min  0.0701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0970 before and 0.0603 after correction.
The Ratio of minimum to maximum transmission is 0.4210.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       Prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1030 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.21(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3093
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0733
_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^)+(0.1084P)^2^+0.8653P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2051
_refine_ls_wR_factor_ref         0.2116
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2785
_reflns_number_total             3093
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03597_si_002.cif
_cod_data_source_block           160308yws_0m_pl
_cod_database_code               1545213
_diffrn_number_total             2330
_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. Restrained distances
 C7-C6
 1.52 with sigma of 0.02
 O4-C6'A
 1.2 with sigma of 0.02
 O3-C7'_$1 = O3-C6
 1.45 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C19 \\sim C4: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C19) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Fixed Sof: O3(0.5) O4(0.5) N1(0.5) C6'A(0.5) H5(0.5) C6(0.5) H6(0.5) C7(0.5)
 H7(0.5) C7'(0.5)
5.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C15(H15)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B)
5.c Aromatic/amide H refined with riding coordinates:
 C14(H14)
5.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              20703
_shelx_hkl_checksum              533
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'