Callistrilones A and B, Triketone-Phloroglucinol-Monoterpene Hybrids with a New Skeleton from Callistemon rigidus.
Cao, Jia-Qing; Huang, Xiao-Jun; Li, Yu-Ting; Wang, Ying; Wang, Lei; Jiang, Ren-Wang; Ye, Wen-Cai; Organic letters 18 (2016) 120–123; doi:10.1021/acs.orglett.5b03360

data_1542386
_publ_section_title
;
 Callistrilones A and B, Triketone-Phloroglucinol-Monoterpene Hybrids with
 a New Skeleton from Callistemon rigidus.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              120
_journal_page_last               123
_journal_paper_doi               10.1021/acs.orglett.5b03360
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C21 H28 O4'
_chemical_formula_sum            'C21 H28 O4'
_chemical_formula_weight         344.44
_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
_audit_creation_date             2015-11-21
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.077(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.8562(2)
_cell_length_b                   9.9924(3)
_cell_length_c                   11.4351(3)
_cell_measurement_reflns_used    7396
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      62.8750
_cell_measurement_theta_min      5.1660
_cell_volume                     977.11(5)
_computing_cell_refinement       'CrysAlis PRO '
_computing_data_collection       'CrysAlis PRO '
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Oxford Gemini S ultra'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13592
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        62.695
_diffrn_reflns_theta_max         62.695
_diffrn_reflns_theta_min         5.172
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.623
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1317 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3073
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0603P)^2^+0.1571P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.0991
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_full    0.963
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                2987
_reflns_number_total             3073
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03360_si_004.cif
_cod_data_source_block           b1b8
_cod_original_cell_volume        977.10(5)
_cod_database_code               1542386
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H3(0.065) H2A(0.041) H6A(0.046) H7A(0.047) H8A(0.043) H9A(0.042)
 H9B(0.042) H9AA(0.039) H2'A(0.059) H3'A(0.143) H3'B(0.143) H3'C(0.143)
 H4'A(0.099) H4'B(0.099) H4'C(0.099) H5'A(0.07) H5'B(0.07) H5'C(0.07)
 H6'A(0.05) H7'A(0.107) H7'B(0.107) H7'C(0.107) H8'A(0.088) H8'B(0.088)
 H8'C(0.088) H9'A(0.069) H9'B(0.069) H9'C(0.069)
 Fixed X: H3(0.0269) H2A(0.0857) H6A(0.8086) H7A(0.8271) H8A(0.6192)
 H9A(0.6242) H9B(0.781) H9AA(0.5761) H2'A(0.44) H3'A(0.237) H3'B(0.3918)
 H3'C(0.2619) H4'A(0.5861) H4'B(0.5556) H4'C(0.4582) H5'A(0.7131) H5'B(0.8647)
 H5'C(0.8066) H6'A(0.9355) H7'A(0.8825) H7'B(0.9308) H7'C(0.7544) H8'A(0.7724)
 H8'B(0.6872) H8'C(0.8636) H9'A(0.2143) H9'B(0.1086) H9'C(0.1497)
 Fixed Y: H3(0.5557) H2A(0.6724) H6A(0.6033) H7A(0.5042) H8A(0.5997)
 H9A(0.8252) H9B(0.8416) H9AA(0.92) H2'A(0.7037) H3'A(0.6929) H3'B(0.6376)
 H3'C(0.5382) H4'A(0.5207) H4'B(0.5139) H4'C(0.4238) H5'A(0.9564) H5'B(0.8978)
 H5'C(0.8422) H6'A(0.6528) H7'A(0.4233) H7'B(0.456) H7'C(0.4328) H8'A(0.7822)
 H8'B(0.6519) H8'C(0.6752) H9'A(0.8369) H9'B(0.8514) H9'C(0.7089)
 Fixed Z: H3(-0.2944) H2A(-0.018) H6A(-0.0975) H7A(0.0765) H8A(0.1642)
 H9A(0.1956) H9B(0.1578) H9AA(0.0018) H2'A(-0.3921) H3'A(-0.5696) H3'B(-0.5938)
 H3'C(-0.5774) H4'A(-0.4243) H4'B(-0.2954) H4'C(-0.4004) H5'A(-0.1494) H5'B(-
 0.0612) H5'C(-0.1935) H6'A(0.2876) H7'A(0.2546) H7'B(0.3934) H7'C(0.3265)
 H8'A(0.3749) H8'B(0.3998) H8'C(0.4668) H9'A(0.252) H9'B(0.1194) H9'C(0.1762)
;
_shelx_res_checksum              37225
_shelx_hkl_checksum              11571
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'