Exploring sesquiterpene alkaloid-like scaffolds via Beckmann-transannular remodelling of beta-caryophyllene
Ma, Shuang-Jiang; Yu, Jie; Fan, Hua-Fang; Li, Zi-Han; Zhang, An-Ling; Zhang, Qiang; RSC Adv. 7 (2017) 40510–; doi:10.1039/C7RA08196K

data_7228944
_publ_section_title
;
 Exploring sesquiterpene alkaloid-like scaffolds
 via&#x00A0;Beckmann-transannular remodelling of beta-caryophyllene
;
_journal_issue                   64
_journal_name_full               'RSC Adv.'
_journal_page_first              40510
_journal_paper_doi               10.1039/C7RA08196K
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H26 N2 O2'
_chemical_formula_sum            'C16 H26 N2 O2'
_chemical_formula_weight         278.39
_chemical_name_systematic
'(3aR,5aR,7aS,E)-2,3a,6,6-tetramethyl-3a,4,5,5a,6,7,7a,9,10,10a-decahydro-8H-cyclobuta[6,7]cyclonona[1,2-d]oxazol-8-one oxime'
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-05-29
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2017-05-29 deposited with the CCDC.
2017-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.970(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.9540(4)
_cell_length_b                   8.9365(5)
_cell_length_c                   10.4047(5)
_cell_measurement_reflns_used    3779
_cell_measurement_temperature    296
_cell_measurement_theta_max      68.540
_cell_measurement_theta_min      4.314
_cell_volume                     819.98(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5699
_diffrn_reflns_point_group_measured_fraction_full 0.801
_diffrn_reflns_point_group_measured_fraction_max 0.799
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.540
_diffrn_reflns_theta_min         4.314
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0703 before and 0.0338 after correction. The Ratio of minimum to maximum transmission is 0.9112. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_description       needle
_exptl_crystal_F_000             304
_exptl_crystal_preparation       'in methanol'
_exptl_crystal_recrystallization_method 'colourless needle'
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 784 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(11)
_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     186
_refine_ls_number_reflns         2415
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0338
_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^)+(0.0644P)^2^+0.0392P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0944
_reflns_Friedel_coverage         0.529
_reflns_Friedel_fraction_full    0.598
_reflns_Friedel_fraction_max     0.594
_reflns_number_gt                2315
_reflns_number_total             2415
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra08196k2.cif
_cod_data_source_block           cu_20170301wp_0m
_cod_database_code               7228944
_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.a Ternary CH refined with riding coordinates:
 C006(H006), C00A(H00A), C00C(H00D)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00B,H00C), C00D(H00E,H00F), C00E(H00G,H00H), C00H(H00O,H00P), C00I(H00Q,
 H00R)
2.c Idealised Me refined as rotating group:
 C00F(H00I,H00J,H00K), C00G(H00L,H00M,H00N), C00J(H00S,H00T,H00U), C00K(H00V,
 H00W,H00X)
2.d Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_shelx_res_checksum              35583
_shelx_hkl_checksum              3797
_shelx_shelxl_version_number     2016/6
_olex2_exptl_crystal_mounting_method '10 mg'
_olex2_submission_original_sample_id 29-13
_olex2_submission_special_instructions 'No special instructions were received'