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_1542384
_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         'C35 H46 O6'
_chemical_formula_sum            'C35 H46 O6'
_chemical_formula_weight         562.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2c'
_space_group_name_H-M_alt        'P 1 1 21'
_symmetry_space_group_name_Hall  'P 2c'
_symmetry_space_group_name_H-M   'P 1 1 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            8
_cell_length_a                   9.7832(7)
_cell_length_b                   24.3518(14)
_cell_length_c                   27.7523(19)
_cell_measurement_reflns_used    14852
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      62.8630
_cell_measurement_theta_min      3.6240
_cell_volume                     6611.7(8)
_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 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0490
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            41704
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        63.245
_diffrn_reflns_theta_max         63.245
_diffrn_reflns_theta_min         3.185
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84964
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.131
_exptl_crystal_description       block
_exptl_crystal_F_000             2432
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 4156 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(15)
_refine_ls_extinction_coef       0.00018(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1479
_refine_ls_number_reflns         17101
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0671
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0639P)^2^+7.1624P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1606
_refine_ls_wR_factor_ref         0.1761
_reflns_Friedel_coverage         0.943
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                14363
_reflns_number_total             17101
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03360_si_003.cif
_cod_data_source_block           cvc7d
_cod_original_cell_volume        6611.7(7)
_cod_database_code               1542384
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H8(0.064) H9(0.068) H10(0.064) H11A(0.059) H11B(0.059) H13(0.049)
 H1'A(0.159) H1'B(0.159) H1'C(0.159) H2'A(0.148) H2'B(0.148) H2'C(0.148)
 H3'A(0.142) H3'B(0.142) H3'C(0.142) H4'A(0.129) H4'B(0.129) H4'C(0.129)
 H6'(0.084) H7'A(0.157) H7'B(0.157) H7'C(0.157) H8'A(0.142) H8'B(0.142)
 H8'C(0.142) H9'A(0.092) H9'B(0.092) H9'C(0.092) H10'(0.092) H11C(0.146)
 H11D(0.146) H11E(0.146) H12A(0.185) H12B(0.185) H12C(0.185) H13'(0.065)
 H14A(0.137) H14B(0.137) H14C(0.137) H15A(0.112) H15B(0.112) H15C(0.112)
 H16A(0.078) H16B(0.078) H16C(0.078) H11F(0.053) H8C(0.063) H9C(0.068)
 H10C(0.054) H11G(0.055) H11H(0.055) H13C(0.044) H1DA(0.216) H1DB(0.216)
 H1DC(0.216) H2DA(0.321) H2DB(0.321) H2DC(0.321) H3DA(0.178) H3DB(0.178)
 H3DC(0.178) H4DA(0.178) H4DB(0.178) H4DC(0.178) H6D(0.084) H7DA(0.237)
 H7DB(0.237) H7DC(0.237) H8DA(0.17) H8DB(0.17) H8DC(0.17) H9DA(0.074)
 H9DB(0.074) H9DC(0.074) H10D(0.068) H11I(0.109) H11J(0.109) H11K(0.109)
 H12D(0.114) H12E(0.114) H12F(0.114) H13D(0.051) H14D(0.087) H14E(0.087)
 H14F(0.087) H15D(0.1) H15E(0.1) H15F(0.1) H16D(0.077) H16E(0.077) H16F(0.077)
 H11L(0.048) H8G(0.082) H9G(0.09) H10G(0.074) H11M(0.065) H11N(0.065)
 H13G(0.044) H1HA(0.119) H1HB(0.119) H1HC(0.119) H2HA(0.136) H2HB(0.136)
 H2HC(0.136) H3HA(0.098) H3HB(0.098) H3HC(0.098) H4HA(0.117) H4HB(0.117)
 H4HC(0.117) H6H(0.056) H7HA(0.119) H7HB(0.119) H7HC(0.119) H8HA(0.105)
 H8HB(0.105) H8HC(0.105) H9HA(0.102) H9HB(0.102) H9HC(0.102) H10H(0.11)
 H11O(0.149) H11P(0.149) H11Q(0.149) H12G(0.242) H12H(0.242) H12I(0.242)
 H13H(0.064) H14G(0.101) H14H(0.101) H14I(0.101) H15G(0.113) H15H(0.113)
 H15I(0.113) H16G(0.074) H16H(0.074) H16I(0.074) H11R(0.049) H8K(0.061)
 H9K(0.062) H10K(0.051) H11S(0.051) H11T(0.051) H13K(0.046) H1LA(0.159)
 H1LB(0.159) H1LC(0.159) H2LA(0.136) H2LB(0.136) H2LC(0.136) H3LA(0.129)
 H3LB(0.129) H3LC(0.129) H4LA(0.116) H4LB(0.116) H4LC(0.116) H6L(0.054)
 H7LA(0.105) H7LB(0.105) H7LC(0.105) H8LA(0.099) H8LB(0.099) H8LC(0.099)
 H9LA(0.091) H9LB(0.091) H9LC(0.091) H10L(0.076) H11U(0.152) H11V(0.152)
 H11W(0.152) H12J(0.141) H12K(0.141) H12L(0.141) H13L(0.061) H14J(0.114)
 H14K(0.114) H14L(0.114) H15J(0.094) H15K(0.094) H15L(0.094) H16J(0.075)
 H16K(0.075) H16L(0.075) H11X(0.047)
 Fixed X: H8(0.5206) H9(0.5156) H10(0.7558) H11A(0.7773) H11B(0.8965)
 H13(1.1865) H1'A(1.2649) H1'B(1.2293) H1'C(1.1156) H2'A(1.4123) H2'B(1.414)
 H2'C(1.4534) H3'A(0.9328) H3'B(0.9059) H3'C(0.9576) H4'A(1.2959) H4'B(1.1742)
 H4'C(1.1992) H6'(0.6566) H7'A(0.5644) H7'B(0.7046) H7'C(0.6909) H8'A(0.5629)
 H8'B(0.6812) H8'C(0.7077) H9'A(0.6647) H9'B(0.6116) H9'C(0.7654) H10'(0.5859)
 H11C(0.5006) H11D(0.6324) H11E(0.5307) H12A(0.8095) H12B(0.7246) H12C(0.8263)
 H13'(1.3336) H14A(1.4404) H14B(1.5339) H14C(1.458) H15A(1.2702) H15B(1.3536)
 H15C(1.4295) H16A(1.2041) H16B(1.098) H16C(1.2308) H11F(0.9094) H8C(-0.0067)
 H9C(-0.0469) H10C(0.1033) H11G(0.3274) H11H(0.2139) H13C(0.7078) H1DA(0.6092)
 H1DB(0.7456) H1DC(0.7157) H2DA(0.9297) H2DB(0.9565) H2DC(0.9683) H3DA(0.453)
 H3DB(0.39) H3DC(0.4432) H4DA(0.6336) H4DB(0.7276) H4DC(0.572) H6D(0.1343)
 H7DA(0.2603) H7DB(0.3607) H7DC(0.3569) H8DA(0.0562) H8DB(0.0268) H8DC(0.1487)
 H9DA(0.2553) H9DB(0.1865) H9DC(0.34) H10D(0.2666) H11I(0.039) H11J(0.1326)
 H11K(0.0357) H12D(0.3629) H12E(0.2328) H12F(0.3297) H13D(0.8152) H14D(0.9615)
 H14E(1.0268) H14F(0.9672) H15D(0.7187) H15E(0.8173) H15F(0.8769) H16D(0.6793)
 H16E(0.5318) H16F(0.6574) H11L(0.3741) H8G(-0.0125) H9G(0.0232) H10G(0.2718)
 H11M(0.2864) H11N(0.4109) H13G(0.6491) H1HA(0.8742) H1HB(0.7876) H1HC(0.8042)
 H2HA(0.7553) H2HB(0.6942) H2HC(0.5972) H3HA(0.2879) H3HB(0.2626) H3HC(0.2967)
 H4HA(0.5878) H4HB(0.4405) H4HC(0.4659) H6H(0.1895) H7HA(-0.0041) H7HB(0.0867)
 H7HC(0.0684) H8HA(0.4056) H8HB(0.3217) H8HC(0.3401) H9HA(0.1519) H9HB(0.0688)
 H9HC(0.2256) H10H(0.3129) H11O(0.1665) H11P(0.1483) H11Q(0.0411) H12G(0.2432)
 H12H(0.0916) H12I(0.1988) H13H(0.7708) H14G(0.6741) H14H(0.7575) H14I(0.8341)
 H15G(0.8958) H15H(0.9725) H15I(0.8959) H16G(0.7118) H16H(0.5937) H16I(0.7103)
 H11R(0.3878) H8K(0.5104) H9K(0.4881) H10K(0.2411) H11S(0.2054) H11T(0.0893)
 H13K(-0.1339) H1LA(-0.3305) H1LB(-0.3097) H1LC(-0.2761) H2LA(-0.1248) H2LB(-
 0.0725) H2LC(0.0228) H3LA(0.0944) H3LB(-0.0262) H3LC(0.1254) H4LA(0.2323)
 H4LB(0.2615) H4LC(0.1935) H6L(0.3143) H7LA(0.1833) H7LB(0.1681) H7LC(0.1008)
 H8LA(0.438) H8LB(0.5132) H8LC(0.4274) H9LA(0.3342) H9LB(0.4158) H9LC(0.2577)
 H10L(0.37) H11U(0.1389) H11V(0.2052) H11W(0.1223) H12J(0.467) H12K(0.3282)
 H12L(0.4111) H13L(-0.2672) H14J(-0.3803) H14K(-0.4588) H14L(-0.3697) H15J(-
 0.166) H15K(-0.2366) H15L(-0.3256) H16J(-0.2088) H16K(-0.104) H16L(-0.2155)
 H11X(0.1016)
 Fixed Y: H8(0.9156) H9(0.9048) H10(0.8987) H11A(1.0063) H11B(0.9708)
 H13(0.7944) H1'A(0.6045) H1'B(0.5545) H1'C(0.597) H2'A(0.6424) H2'B(0.5823)
 H2'C(0.6318) H3'A(0.6582) H3'B(0.6369) H3'C(0.5963) H4'A(0.649) H4'B(0.6658)
 H4'C(0.6038) H6'(0.8167) H7'A(0.7845) H7'B(0.7576) H7'C(0.8217) H8'A(0.7254)
 H8'B(0.7305) H8'C(0.7012) H9'A(1.0239) H9'B(0.9848) H9'C(1.0029) H10'(0.9327)
 H11C(1.0066) H11D(1.0406) H11E(1.0247) H12A(0.9315) H12B(0.9772) H12C(0.9931)
 H13'(0.8474) H14A(0.7882) H14B(0.8016) H14C(0.745) H15A(0.8161) H15B(0.7621)
 H15C(0.8187) H16A(0.954) H16B(0.9681) H16C(0.9351) H11F(0.9776) H8C(0.8058)
 H9C(0.7733) H10C(0.7947) H11G(0.8246) H11H(0.8624) H13C(0.9573) H1DA(1.1419)
 H1DB(1.1375) H1DC(1.19) H2DA(1.1762) H2DB(1.1278) H2DC(1.1179) H3DA(1.1702)
 H3DB(1.1115) H3DC(1.1298) H4DA(1.1506) H4DB(1.0987) H4DC(1.0919) H6D(0.9307)
 H7DA(0.9243) H7DB(0.9699) H7DC(0.9126) H8DA(0.9772) H8DB(1.0119) H8DC(1.0278)
 H9DA(0.741) H9DB(0.7807) H9DC(0.7891) H10D(0.7158) H11I(0.683) H11J(0.646)
 H11K(0.6895) H12D(0.7489) H12E(0.7296) H12F(0.6861) H13D(0.8985) H14D(0.9542)
 H14E(0.9363) H14F(0.9957) H15D(0.9301) H15E(0.9808) H15F(0.9215) H16D(0.7955)
 H16E(0.7894) H16F(0.7965) H11L(0.7848) H8G(0.3058) H9G(0.3177) H10G(0.3347)
 H11M(0.2273) H11N(0.2642) H13G(0.4497) H1HA(0.6158) H1HB(0.6055) H1HC(0.6652)
 H2HA(0.6404) H2HB(0.6913) H2HC(0.651) H3HA(0.6427) H3HB(0.5816) H3HC(0.5955)
 H4HA(0.6101) H4HB(0.5908) H4HC(0.6518) H6H(0.3833) H7HA(0.4378) H7HB(0.4828)
 H7HC(0.4254) H8HA(0.4183) H8HB(0.4132) H8HC(0.4707) H9HA(0.2074) H9HB(0.2453)
 H9HC(0.2361) H10H(0.2615) H11O(0.1971) H11P(0.2013) H11Q(0.2287) H12G(0.3433)
 H12H(0.3224) H12I(0.2949) H13H(0.4032) H14G(0.446) H14H(0.4994) H14I(0.4454)
 H15G(0.4534) H15H(0.4499) H15I(0.5039) H16G(0.2933) H16H(0.2751) H16I(0.3136)
 H11R(0.263) H8K(0.548) H9K(0.5555) H10K(0.573) H11S(0.4702) H11T(0.5089)
 H13K(0.705) H1LA(0.8833) H1LB(0.8772) H1LC(0.933) H2LA(0.8912) H2LB(0.9411)
 H2LC(0.8903) H3LA(0.9025) H3LB(0.8617) H3LC(0.8409) H4LA(0.8932) H4LB(0.8312)
 H4LC(0.8479) H6L(0.6392) H7LA(0.6782) H7LB(0.7323) H7LC(0.6777) H8LA(0.684)
 H8LB(0.6908) H8LC(0.7395) H9LA(0.4531) H9LB(0.4919) H9LC(0.4846) H10L(0.5277)
 H11U(0.5307) H11V(0.4794) H11W(0.4724) H12J(0.4592) H12K(0.4271) H12L(0.4341)
 H13L(0.6643) H14J(0.7204) H14K(0.7189) H14L(0.7701) H15J(0.7031) H15K(0.7593)
 H15L(0.7081) H16J(0.5495) H16K(0.5308) H16L(0.5748) H11X(0.5133)
 Fixed Z: H8(0.4294) H9(0.3517) H10(0.3223) H11A(0.359) H11B(0.3378)
 H13(0.3459) H1'A(0.2926) H1'B(0.3259) H1'C(0.3121) H2'A(0.4059) H2'B(0.3855)
 H2'C(0.3521) H3'A(0.4824) H3'B(0.43) H3'C(0.4698) H4'A(0.4807) H4'B(0.5144)
 H4'C(0.502) H6'(0.5057) H7'A(0.5784) H7'B(0.5923) H7'C(0.5901) H8'A(0.5041)
 H8'B(0.4663) H8'C(0.5157) H9'A(0.4506) H9'B(0.4913) H9'C(0.4904) H10'(0.2704)
 H11C(0.3157) H11D(0.3039) H11E(0.2626) H12A(0.2436) H12B(0.2174) H12C(0.2588)
 H13'(0.3933) H14A(0.3394) H14B(0.3838) H14C(0.3808) H15A(0.4699) H15B(0.4612)
 H15C(0.4641) H16A(0.331) H16B(0.3715) H16C(0.3842) H11F(0.4224) H8C(0.6359)
 H9C(0.7076) H10C(0.7701) H11G(0.7524) H11H(0.7303) H13C(0.7151) H1DA(0.7445)
 H1DB(0.7739) H1DC(0.743) H2DA(0.6964) H2DB(0.7323) H2DC(0.6767) H3DA(0.6285)
 H3DB(0.6216) H3DC(0.6724) H4DA(0.5627) H4DB(0.5668) H4DC(0.5546) H6D(0.556)
 H7DA(0.4806) H7DB(0.4989) H7DC(0.5245) H8DA(0.4913) H8DB(0.5378) H8DC(0.5039)
 H9DA(0.6085) H9DB(0.5712) H9DC(0.5857) H10D(0.7212) H11I(0.7225) H11J(0.7549)
 H11K(0.7787) H12D(0.7937) H12E(0.822) H12F(0.7982) H13D(0.661) H14D(0.705)
 H14E(0.6558) H14F(0.6618) H15D(0.5887) H15E(0.5897) H15F(0.5837) H16D(0.7379)
 H16E(0.7165) H16F(0.682) H11L(0.6773) H8G(0.6658) H9G(0.7443) H10G(0.7526)
 H11M(0.7177) H11N(0.7325) H13G(0.7141) H1HA(0.6861) H1HB(0.6394) H1HC(0.6597)
 H2HA(0.764) H2HB(0.737) H2HC(0.7648) H3HA(0.6423) H3HB(0.6268) H3HC(0.6806)
 H4HA(0.5775) H4HB(0.5631) H4HC(0.5786) H6H(0.532) H7HA(0.5186) H7HB(0.494)
 H7HC(0.4694) H8HA(0.5157) H8HB(0.4678) H8HC(0.4924) H9HA(0.6301) H9HB(0.5951)
 H9HC(0.5867) H10H(0.8088) H11O(0.775) H11P(0.831) H11Q(0.7967) H12G(0.8352)
 H12H(0.8347) H12I(0.8691) H13H(0.6519) H14G(0.5843) H14H(0.5957) H14I(0.5811)
 H15G(0.7081) H15H(0.6586) H15I(0.6732) H16G(0.7237) H16H(0.6891) H16I(0.6701)
 H11R(0.6475) H8K(0.9029) H9K(0.8249) H10K(0.8077) H11S(0.8516) H11T(0.8324)
 H13K(0.8389) H1LA(0.8271) H1LB(0.8829) H1LC(0.8575) H2LA(0.772) H2LB(0.8026)
 H2LC(0.7939) H3LA(0.9702) H3LB(0.9802) H3LC(0.9825) H4LA(0.8943) H4LB(0.9056)
 H4LC(0.8566) H6L(1.0272) H7LA(1.0894) H7LB(1.0592) H7LC(1.041) H8LA(1.0875)
 H8LB(1.038) H8LC(1.0591) H9LA(0.94) H9LB(0.9747) H9LC(0.9812) H10L(0.7496)
 H11U(0.7355) H11V(0.7107) H11W(0.7587) H12J(0.798) H12K(0.7979) H12L(0.7499)
 H13L(0.9006) H14J(0.844) H14K(0.8932) H14L(0.8797) H15J(0.9688) H15K(0.957)
 H15L(0.9705) H16J(0.8314) H16K(0.8708) H16L(0.8833) H11X(0.9175)
;
_shelx_res_checksum              6988
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'