Organocatalytic and Late-Stage CH-Functionalization Enabled Asymmetric Synthesis of Communesin F and Putative Communesins.
Park, Jisook; Jean, Alexandre; Chen, David Y.-K.; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b02426

data_4033125
_publ_section_title
;
 Organocatalytic and Late-Stage CH-Functionalization Enabled Asymmetric
 Synthesis of Communesin F and Putative Communesins.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b02426
_journal_year                    2017
_chemical_formula_moiety         'C39 H44 N6 O5'
_chemical_formula_sum            'C39 H44 N6 O5'
_chemical_formula_weight         676.80
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-05-01
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                76.458(4)
_cell_angle_beta                 72.862(4)
_cell_angle_gamma                75.076(4)
_cell_formula_units_Z            2
_cell_length_a                   11.4742(10)
_cell_length_b                   13.6344(14)
_cell_length_c                   14.6597(15)
_cell_measurement_reflns_used    9142
_cell_measurement_temperature    305.3
_cell_measurement_theta_max      23.86
_cell_measurement_theta_min      2.33
_cell_volume                     2086.3(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      305.3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            79276
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.283
_diffrn_reflns_theta_min         2.200
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0851 before and 0.0769 after correction.
The Ratio of minimum to maximum transmission is 0.9353.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.077
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         8380
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0627
_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^)+(0.1237P)^2^+0.2126P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2004
_refine_ls_wR_factor_ref         0.2170
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5312
_reflns_number_total             8380
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02426_si_001.cif
_cod_data_source_block           JS-4-032_B[Moon371]
_cod_database_code               4033125
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H5(0.079) H6(0.091) H7(0.082) H8(0.066) H13(0.069) H14(0.087)
 H15(0.093) H16(0.079) H20A(0.07) H20B(0.07) H21A(0.058) H21B(0.058)
 H22A(0.078) H22B(0.078) H24(0.075) H25(0.075) H27(0.074) H28(0.076)
 H33A(0.112) H33B(0.112) H33C(0.112) H34A(0.058) H34B(0.058) H35A(0.069)
 H35B(0.069) H41A(0.141) H41B(0.141) H42A(0.152) H42B(0.152) H42C(0.152)
 H45A(0.158) H45B(0.158) H45C(0.158) H46(0.092) H47A(0.162) H47B(0.162)
 H47C(0.162) H48A(0.196) H48B(0.196) H48C(0.196) H49(0.105) H50A(0.22)
 H50B(0.22) H50C(0.22)
 Fixed X: H5(-0.0141) H6(-0.0827) H7(0.0547) H8(0.2599) H13(0.6369)
 H14(0.7966) H15(0.7599) H16(0.5685) H20A(0.6041) H20B(0.4806) H21A(0.4998)
 H21B(0.3844) H22A(0.6044) H22B(0.6076) H24(0.8073) H25(1.0161) H27(0.9544)
 H28(0.7458) H33A(0.3129) H33B(0.3695) H33C(0.2348) H34A(0.2381) H34B(0.3674)
 H35A(0.3943) H35B(0.296) H41A(0.1365) H41B(0.0063) H42A(-0.0533) H42B(-0.005)
 H42C(0.0618) H45A(-0.1071) H45B(-0.0537) H45C(-0.1304) H46(0.0772) H47A(-
 0.0101) H47B(-0.0279) H47C(0.1051) H48A(0.168) H48B(0.1953) H48C(0.3031)
 H49(0.3076) H50A(0.4063) H50B(0.3598) H50C(0.2845)
 Fixed Y: H5(0.6545) H6(0.768) H7(0.7984) H8(0.7101) H13(0.3831) H14(0.2926)
 H15(0.2585) H16(0.3179) H20A(0.6092) H20B(0.6938) H21A(0.4857) H21B(0.5609)
 H22A(0.7599) H22B(0.7944) H24(0.7781) H25(0.699) H27(0.4857) H28(0.5666)
 H33A(0.5001) H33B(0.3819) H33C(0.4195) H34A(0.432) H34B(0.3817) H35A(0.2477)
 H35B(0.3057) H41A(0.1094) H41B(0.1768) H42A(0.3509) H42B(0.3739) H42C(0.4036)
 H45A(0.0996) H45B(0.0015) H45C(-0.0083) H46(-0.0654) H47A(0.1166) H47B(0.0063)
 H47C(0.0325) H48A(-0.1361) H48B(-0.0739) H48C(-0.1538) H49(0.02) H50A(-0.1127)
 H50B(-0.0091) H50C(-0.0976)
 Fixed Z: H5(0.894) H6(0.767) H7(0.6185) H8(0.5944) H13(0.6854) H14(0.7592)
 H15(0.9244) H16(1.022) H20A(0.5231) H20B(0.5237) H21A(0.6053) H21B(0.5724)
 H22A(0.6962) H22B(0.5858) H24(0.4861) H25(0.4483) H27(0.6868) H28(0.7235)
 H33A(1.0723) H33B(1.0925) H33C(1.0764) H34A(0.7527) H34B(0.6918) H35A(0.8108)
 H35B(0.8903) H41A(0.9522) H41B(1.0034) H42A(0.9427) H42B(0.8297) H42C(0.8954)
 H45A(0.8036) H45B(0.8711) H45C(0.8022) H46(0.7368) H47A(0.62) H47B(0.6203)
 H47C(0.5819) H48A(0.8432) H48B(0.9093) H48C(0.8563) H49(0.7799) H50A(0.6877)
 H50B(0.6231) H50C(0.6538)
;
_shelx_res_checksum              17964
_shelx_hkl_checksum              97908
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'