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_1542385
_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         'C34 H44 O7'
_chemical_formula_sum            'C34 H44 O7'
_chemical_formula_weight         564.69
_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
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4131(2)
_cell_length_b                   14.8983(7)
_cell_length_c                   32.7256(14)
_cell_measurement_reflns_used    10031
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      62.7570
_cell_measurement_theta_min      4.9560
_cell_volume                     3126.7(2)
_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  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Oxford Gemini S ultra'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1073
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            27092
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        63.251
_diffrn_reflns_theta_max         63.251
_diffrn_reflns_theta_min         3.259
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 1785 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         5028
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0585
_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^)+(0.0936P)^2^+0.6524P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1500
_refine_ls_wR_factor_ref         0.1624
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                4670
_reflns_number_total             5028
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03360_si_002.cif
_cod_data_source_block           cv2
_cod_original_cell_volume        3126.8(2)
_cod_database_code               1542385
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H4(0.06) H8A(0.048) H8B(0.048) H9A(0.049) H10A(0.052) H11A(0.047)
 H13A(0.039) H7BA(0.038) H1'A(0.091) H1'B(0.091) H1'C(0.091) H2'A(0.089)
 H2'B(0.089) H2'C(0.089) H3'A(0.083) H3'B(0.083) H3'C(0.083) H4'A(0.078)
 H4'B(0.078) H4'C(0.078) H6'A(0.043) H7'A(0.07) H7'B(0.07) H7'C(0.07)
 H8'A(0.086) H8'B(0.086) H8'C(0.086) H9'A(0.052) H10B(0.099) H10C(0.099)
 H10D(0.099) H11B(0.101) H11C(0.101) H11D(0.101) H12A(0.055) H12B(0.055)
 H12C(0.055) H13B(0.047) H14A(0.075) H14B(0.075) H14C(0.075) H15A(0.084)
 H15B(0.084) H15C(0.084)
 Fixed X: H4(0.0578) H8A(0.5308) H8B(0.663) H9A(0.8539) H10A(0.9317)
 H11A(0.735) H13A(0.3958) H7BA(0.3176) H1'A(0.092) H1'B(-0.024) H1'C(-0.0569)
 H2'A(0.4433) H2'B(0.4999) H2'C(0.3233) H3'A(-0.2124) H3'B(-0.2353) H3'C(-
 0.2406) H4'A(0.1226) H4'B(0.3069) H4'C(0.1076) H6'A(-0.1545) H7'A(-0.3191)
 H7'B(-0.4832) H7'C(-0.4699) H8'A(-0.2396) H8'B(-0.4201) H8'C(-0.4334)
 H9'A(0.5495) H10B(0.4131) H10C(0.6094) H10D(0.4545) H11B(0.8923) H11C(0.7493)
 H11D(0.9042) H12A(0.3541) H12B(0.3812) H12C(0.1985) H13B(0.115) H14A(-0.1572)
 H14B(-0.152) H14C(-0.2184) H15A(0.2909) H15B(0.0588) H15C(0.1253)
 Fixed Y: H4(1.1657) H8A(1.0805) H8B(1.0438) H9A(1.0243) H10A(0.8661)
 H11A(0.7812) H13A(0.8677) H7BA(0.9554) H1'A(0.81) H1'B(0.8849) H1'C(0.8772)
 H2'A(0.8656) H2'B(0.9676) H2'C(0.9374) H3'A(1.1173) H3'B(1.1102) H3'C(1.0232)
 H4'A(1.2012) H4'B(1.1604) H4'C(1.1965) H6'A(1.1874) H7'A(1.0543) H7'B(1.1194)
 H7'C(1.1095) H8'A(1.3227) H8'B(1.2752) H8'C(1.2851) H9'A(0.9077) H10B(1.0526)
 H10C(1.0846) H10D(1.0153) H11B(0.881) H11C(0.9099) H11D(0.9792) H12A(0.7904)
 H12B(0.7394) H12C(0.8082) H13B(0.7779) H14A(0.882) H14B(0.8707) H14C(0.7899)
 H15A(0.7275) H15B(0.6944) H15C(0.7751)
 Fixed Z: H4(0.7764) H8A(0.741) H8B(0.7777) H9A(0.7186) H10A(0.7273)
 H11A(0.7726) H13A(0.9065) H7BA(0.7412) H1'A(1.0328) H1'B(1.0576) H1'C(1.0103)
 H2'A(1.0591) H2'B(1.0549) H2'C(1.085) H3'A(1.0124) H3'B(0.9648) H3'C(0.9917)
 H4'A(1.0053) H4'B(0.9799) H4'C(0.9575) H6'A(0.9047) H7'A(0.8837) H7'B(0.9032)
 H7'C(0.8556) H8'A(0.873) H8'B(0.849) H8'C(0.8966) H9'A(0.6852) H10B(0.6825)
 H10C(0.6579) H10D(0.6384) H11B(0.6626) H11C(0.6261) H11D(0.6455) H12A(0.7361)
 H12B(0.7777) H12C(0.7722) H13B(0.932) H14A(0.9258) H14B(0.8781) H14C(0.906)
 H15A(0.8738) H15B(0.8739) H15C(0.8461)
;
_shelx_res_checksum              33161
_shelx_hkl_checksum              30502
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'