Norsampsone E, an unprecedented decarbonyl polycyclic polyprenylated acylphloroglucinol with a homoadamantyl core from Hypericum sampsonii
Tian, Wen-Jing; Qiu, Yu-Qin; Chen, Jun-Jie; Yao, Xiao-Jun; Wang, Guang-Hui; Dai, Yi; Chen, Hai-Feng; Yao, Xin-Sheng; RSC Adv. 7 (2017) 33113–; doi:10.1039/C7RA05947G

data_7228606
_publ_section_title
;
 Norsampsone E, an unprecedented decarbonyl polycyclic polyprenylated
 acylphloroglucinol with a homoadamantyl core from Hypericum sampsonii
;
_journal_issue                   53
_journal_name_full               'RSC Adv.'
_journal_page_first              33113
_journal_paper_doi               10.1039/C7RA05947G
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C33 H42 O5'
_chemical_formula_sum            'C33 H42 O5'
_chemical_formula_weight         518.66
_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             2017-05-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-05-23 deposited with the CCDC.
2017-06-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.15822(19)
_cell_length_b                   17.0208(3)
_cell_length_c                   24.2524(4)
_cell_measurement_reflns_used    5462
_cell_measurement_temperature    150.05(10)
_cell_measurement_theta_max      69.157
_cell_measurement_theta_min      3.059
_cell_volume                     5844.45(16)
_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      150.05(10)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega -110.00  -59.00   1.0000    1.0200
omega____ theta____ kappa____ phi______ frames
    -      -35.3849 -179.0000 -120.0000 51

  2 omega   40.00   87.00   1.0000    1.0200
omega____ theta____ kappa____ phi______ frames
    -       35.3849  179.0000   60.0000 47

  3 omega   17.00  102.00   1.0000    1.0200
omega____ theta____ kappa____ phi______ frames
    -       35.3849   57.0000 -180.0000 85

  4 omega   81.00  149.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       86.3500   61.0000 -180.0000 68

  5 omega   22.00   67.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       86.3500  -94.0000 -180.0000 45

  6 omega   67.00  153.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       86.3500   61.0000   60.0000 86

  7 omega   27.00   77.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       86.3500  -45.0000 -150.0000 50

  8 omega   76.00  155.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       86.3500   45.0000  150.0000 79

  9 omega   73.00  140.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       86.3500   61.0000   90.0000 67

 10 omega  115.00  156.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       86.3500   -6.0000   65.4421 41

 11 omega   21.00   99.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       86.3500   -6.0000   65.4421 78
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_orient_matrix_UB_11      0.0341815000
_diffrn_orient_matrix_UB_12      0.0541668000
_diffrn_orient_matrix_UB_13      0.0467481000
_diffrn_orient_matrix_UB_21      -0.0916556000
_diffrn_orient_matrix_UB_22      -0.0163150000
_diffrn_orient_matrix_UB_23      0.0322753000
_diffrn_orient_matrix_UB_31      0.0474799000
_diffrn_orient_matrix_UB_32      -0.0706516000
_diffrn_orient_matrix_UB_33      0.0285261000
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20563
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        61.045
_diffrn_reflns_theta_max         61.045
_diffrn_reflns_theta_min         4.061
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  0.884
_exptl_absorpt_correction_T_min  0.884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_description       block
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 3439 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     703
_refine_ls_number_reflns         8816
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0539P)^2^+0.9712P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1022
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                8314
_reflns_number_total             8816
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra05947g2.cif
_cod_data_source_block           tianwenjing-f-abs
_cod_original_cell_volume        5844.44(16)
_cod_database_code               7228606
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         CHO
_shelx_estimated_absorpt_t_max   0.886
_shelx_estimated_absorpt_t_min   0.886
_reflns_odcompleteness_completeness 98.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_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, All O(H) groups
2. Rigid bond restraints
 C61, C66A, C70A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C61 \\sim C66A \\sim C70A: within 2A with sigma of 0.005 and sigma for terminal
atoms of 0.01
4.a Ternary CH refined with riding coordinates:
 C30(H30), C34(H34), C53(H53), C42(H42), C47(H47), C52(H52)
4.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C38(H38A,H38B), C60(H60A,H60B), C67(H67A,H67B), C32(H32A,
 H32B), C49(H49A,H49B), C55(H55A,H55B), C62(H62A,H62B)
4.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C36(H36), C40(H40), C41(H41), C44(H44), C57(H57), C31(H31),
 C45(H45), C61(H61), C66A(H66A), C70A(H70A), C73(H73)
4.d Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C56(H56A,H56B,H56C), C58(H58A,H58B,H58C), C59(H59A,H59B,
 H59C), C65(H65A,H65B,H65C), C68(H68A,H68B,H68C), C71(H71A,H71B,H71C), C72(H72A,
 H72B,H72C), C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C17(H17A,H17B,H17C), C24(H24A,
 H24B,H24C), C43(H43A,H43B,H43C), C46(H46A,H46B,H46C), C69(H69A,H69B,H69C),
 C74(H74A,H74B,H74C)
4.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O13(H13)
;
_olex2_submission_special_instructions 'No special instructions were received'