The four-step total synthesis of (‒)-chaetominine
Qi-Long Peng; Shi-Peng Luo; Xiao-Er Xia; Liang-Xian Liu; Pei-Qiang Huang; Chem.Commun. 50 (2014) 1986–; doi:10.1039/c3cc48833k

data_7111954
_publ_section_title
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 The four-step total synthesis of (--)-chaetominine
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_journal_name_full               Chem.Commun.
_journal_page_first              1986
_journal_paper_doi               10.1039/c3cc48833k
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         '0.5(C23 H23 N4 O5)'
_chemical_formula_sum            'C11.5 H11.5 N2 O2.5'
_chemical_formula_weight         217.73
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_symmetry_Int_Tables_number      144
_symmetry_space_group_name_Hall  'P 31'
_symmetry_space_group_name_H-M   'P 31'
_audit_creation_date             2013-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            12
_cell_length_a                   10.6073(15)
_cell_length_b                   10.6073(15)
_cell_length_c                   35.206(10)
_cell_measurement_reflns_used    3659
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      20.37
_cell_measurement_theta_min      2.22
_cell_volume                     3430.5(12)
_computing_cell_refinement       'SAINT v6.28A (Bruker, 2002)'
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_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)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.8412
_diffrn_measured_fraction_theta_max 0.8412
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_av_unetI/netI     0.1016
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            21093
_diffrn_reflns_theta_full        24.9958
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.2646
_exptl_crystal_F_000             1374.7182
_refine_diff_density_max         0.9742
_refine_diff_density_min         -0.3643
_refine_diff_density_rms         0.0978
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -2.4(7)
_refine_ls_d_res_high            0.8410
_refine_ls_d_res_low             11.7354
_refine_ls_goodness_of_fit_ref   0.9916
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    83
_refine_ls_number_parameters     564
_refine_ls_number_reflns         6802
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9916
_refine_ls_R_factor_all          0.1316
_refine_ls_R_factor_gt           0.0973
_refine_ls_shift/su_max          0.1210
_refine_ls_shift/su_mean         0.0205
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1981P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2628
_refine_ls_wR_factor_ref         0.2887
_reflns_Friedel_coverage         0.683
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              41
_reflns_limit_l_min              -33
_reflns_number_gt                4383
_reflns_number_total             6802
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c3cc48833k.txt
_cod_data_source_block           a
_cod_database_code               7111954
_olex2_refinement_description
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1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C22(H22), C25(H25), C16(H16), C19(H19), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C26(H26a,H26b), C31(H31a,H31b)
2.c Me refined with riding coordinates:
 C57(H57a,H57b,H57c), C47(H47a,H47b,H47c), C58(H58a,H58b,H58c), C61(H61a,H61b,
 H61c)
2.d Aromatic/amide H refined with riding coordinates:
 N14(H14), C27(H27), N11(H11a), C38(H38), C40(H40), C43(H43), C45(H45),
 C55(H55), C56(H56), C60(H60), C62(H62), N4(H4), C28(H28), C35(H35), N1(H1a),
 C41(H41), C44(H44), C50(H50), C103(H103), C104(H104), C105(H105), C106(H106)
2.e Fitted hexagon refined as free rotating group:
 C101(C102,C103,C104,C105,C106)
2.f Tetrahedral OH refined with riding coordinates:
 O11(H11), O1(H1)
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