Crocrassins A and B: two novel sesquiterpenoids with an unprecedented carbon skeleton from Croton crassifolius
Zhang, Zhan-Xin; Li, Hui-Hong; Qi, Feng-Ming; Dong, Le-Le; Hai, Yang; Fan, Gai-Xia; Fei, Dong-Qing; RSC Advances 4 (2014) 30059–; doi:10.1039/C4RA03798G

data_7217093
_publ_section_title
;
 Crocrassins A and B: two novel sesquiterpenoids with an unprecedented
 carbon skeleton from Croton crassifolius
;
_journal_issue                   57
_journal_name_full               'RSC Advances'
_journal_page_first              30059
_journal_paper_doi               10.1039/C4RA03798G
_journal_volume                  4
_journal_year                    2014
_chemical_absolute_configuration none
_chemical_formula_moiety         'C15 H24 O3'
_chemical_formula_sum            'C15 H24 O3'
_chemical_formula_weight         252.34
_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     iterative
_audit_creation_date             2013-12-17
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   11.2310(5)
_cell_length_b                   17.3234(7)
_cell_length_c                   31.7240(19)
_cell_measurement_reflns_used    5378
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      56.1980
_cell_measurement_theta_min      3.7720
_cell_volume                     6172.2(5)
_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, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0138051000
_diffrn_orient_matrix_UB_12      0.0790183000
_diffrn_orient_matrix_UB_13      -0.0217536000
_diffrn_orient_matrix_UB_21      -0.1113173000
_diffrn_orient_matrix_UB_22      0.0166565000
_diffrn_orient_matrix_UB_23      0.0268571000
_diffrn_orient_matrix_UB_31      0.0789588000
_diffrn_orient_matrix_UB_32      0.0372610000
_diffrn_orient_matrix_UB_33      0.0341009000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            39759
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         72.113
_diffrn_reflns_theta_min         3.778
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.590
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77120
_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_density_diffrn    1.086
_exptl_crystal_description       block
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 2641 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.07(14)
_refine_ls_extinction_coef       0.0016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     674
_refine_ls_number_reflns         11886
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0706
_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^)+(0.1040P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1746
_refine_ls_wR_factor_ref         0.2085
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                7941
_reflns_number_total             11886
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ra03798g2.cif
_cod_data_source_block           feidq1122_cu3
_cod_database_code               7217093
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 94.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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. Uiso/Uaniso restraints and constraints
Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C16)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C46(H46), C50(H50), C51(H51), C52(H52), C31(H31), C35(H35), C36(H36),
 C37(H37), C1(H1A), C5(H5), C6(H6), C7(H7A), C16(H16), C20(H20), C21(H21),
 C22(H22)
3.b Secondary CH2 refined with riding coordinates:
 C47(H47A,H47B), C48(H48A,H48B), C32(H32A,H32B), C33(H33A,H33B), C2(H2A,H2B),
 C3(H3A,H3B), C17(H17A,H17B), C18(H18A,H18B)
3.c X=CH2 refined with riding coordinates:
 C55(H55A,H55B), C40(H40A,H40B), C10(H10A,H10B), C25(H25A,H25B)
3.d Idealised Me refined as rotating group:
 C56(H56A,H56B,H56C), C57(H57A,H57B,H57C), C58(H58A,H58B,H58C), C59(H59A,H59B,
 H59C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C), C44(H44A,
 H44B,H44C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C),
 C14(H14A,H14B,H14C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C)
3.e Idealised tetrahedral OH refined as rotating group:
 O10(H10), O11(H11), O7(H7), O9(H9), O1(H1), O3(H3), O4(H4), O5(H5A)
;
_shelx_res_checksum              33756