A concise approach to the tricyclic framework of longipinane- and ent-longipinane-type sesquiterpenoids
He, Min; Yi, Jiuzhou; Zhao, Gaoyuan; Chen, Peiqi; Long, Dan; Hu, Xiaojun; Li, Huilin; Xie, Xingang; Wang, Xiaolei; She, Xuegong; Organic Chemistry Frontiers 6 (2019) 383–; doi:10.1039/C8QO01235K

data_1554551
_publ_section_title
;
 A concise approach to the tricyclic framework of longipinane- and
 ent-longipinane-type sesquiterpenoids
;
_journal_issue                   3
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              383
_journal_paper_doi               10.1039/C8QO01235K
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C13 H22 O2'
_chemical_formula_sum            'C13 H22 O2'
_chemical_formula_weight         210.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-05-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-06-06 deposited with the CCDC.
2018-12-14 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.8513(6)
_cell_length_b                   8.0917(4)
_cell_length_c                   24.6768(12)
_cell_measurement_reflns_used    1114
_cell_measurement_temperature    295.38(10)
_cell_measurement_theta_max      26.3710
_cell_measurement_theta_min      4.2580
_cell_volume                     2366.4(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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      295.38(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   55.00   81.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000 -150.0000 26

  2 omega  -41.00   76.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867    0.0000   90.0000 117
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0364481000
_diffrn_orient_matrix_UB_12      0.0585023000
_diffrn_orient_matrix_UB_13      0.0123399000
_diffrn_orient_matrix_UB_21      0.0298402000
_diffrn_orient_matrix_UB_22      0.0651178000
_diffrn_orient_matrix_UB_23      -0.0127988000
_diffrn_orient_matrix_UB_31      -0.0369157000
_diffrn_orient_matrix_UB_32      -0.0050277000
_diffrn_orient_matrix_UB_33      -0.0225774000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            5202
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.72
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83300
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.618
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2321
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0642
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0603P)^2^+1.6193P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1520
_refine_ls_wR_factor_ref         0.1749
_reflns_number_gt                1648
_reflns_number_total             2321
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8qo01235k2.cif
_cod_data_source_block           hem_0524
_cod_database_code               1554551
_reflns_odcompleteness_completeness 99.46
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2A), C3(H3), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C4(H4A,H4B), C8(H8A,H8B), C10(H10A,H10B), C9(H9A,H9B)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C12(H12A,H12B,H12C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_olex2_date_sample_data_collection 2018-05-24
_olex2_submission_special_instructions 'No special instructions were received'