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_7228945
_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 syn
_chemical_formula_moiety         'C14 H23 N O2'
_chemical_formula_sum            'C14 H23 N O2'
_chemical_formula_weight         237.33
_chemical_name_systematic        MSJ42-11
_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     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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1257(8)
_cell_length_b                   10.3350(10)
_cell_length_c                   16.0543(15)
_cell_measurement_reflns_used    4310
_cell_measurement_temperature    293
_cell_measurement_theta_max      68.445
_cell_measurement_theta_min      6.104
_cell_volume                     1348.2(2)
_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 0.992
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5708
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.445
_diffrn_reflns_theta_min         6.104
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0495 before and 0.0358 after correction.
The Ratio of minimum to maximum transmission is 0.8367.
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    1.169
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_preparation       'in MeOH-water'
_exptl_crystal_recrystallization_method -
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 906 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       0.021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0412
_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^)+(0.0739P)^2^+0.1500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1199
_reflns_Friedel_coverage         0.672
_reflns_Friedel_fraction_full    0.940
_reflns_Friedel_fraction_max     0.928
_reflns_number_gt                2304
_reflns_number_total             2387
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra08196k2.cif
_cod_data_source_block           cu_20161118_0m
_cod_database_code               7228945
_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:
 C004(H004), C007(H007), C008(H008)
2.b Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00C(H00F,H00G), C00E(H00H,H00I), C00H(H00P,H00Q), C009(H00R,
 H00S)
2.c Idealised Me refined as rotating group:
 C00B(H00C,H00D,H00E), C00F(H00J,H00K,H00L), C00G(H00M,H00N,H00O)
2.d Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_shelx_res_checksum              25302
_shelx_hkl_checksum              17881
_shelx_shelxl_version_number     2016/6
_olex2_exptl_crystal_mounting_method -
_olex2_submission_original_sample_id MSJ42-11
_olex2_submission_special_instructions 'No special instructions were received'