Total Synthesis of (-)-Chanoclavine I and an Oxygen-Substituted Ergoline Derivative.
Lu, Jia-Tian; Shi, Zi-Fa; Cao, Xiao-Ping; The Journal of organic chemistry 82 (2017) 7774–7782; doi:10.1021/acs.joc.7b00573

data_4032642
_publ_section_title
;
 Total Synthesis of (-)-Chanoclavine I and an Oxygen-Substituted Ergoline
 Derivative.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7774
_journal_page_last               7782
_journal_paper_doi               10.1021/acs.joc.7b00573
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H20 N2 O'
_chemical_formula_sum            'C16 H20 N2 O'
_chemical_formula_weight         256.34
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-03
_audit_creation_method
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7997(4)
_cell_length_b                   10.3121(5)
_cell_length_c                   15.5615(9)
_cell_measurement_reflns_used    888
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.1650
_cell_measurement_theta_min      3.9410
_cell_volume                     1412.10(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega   35.00   75.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  178.0000    0.0000 40

  2 omega  -30.00   44.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -57.0000 -180.0000 74

  3 omega   24.00   65.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305   57.0000  150.0000 41
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0346239000
_diffrn_orient_matrix_UB_12      -0.0589692000
_diffrn_orient_matrix_UB_13      0.0129859000
_diffrn_orient_matrix_UB_21      -0.0648244000
_diffrn_orient_matrix_UB_22      -0.0348040000
_diffrn_orient_matrix_UB_23      -0.0141426000
_diffrn_orient_matrix_UB_31      0.0330604000
_diffrn_orient_matrix_UB_32      -0.0066122000
_diffrn_orient_matrix_UB_33      -0.0413447000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0663
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3705
_diffrn_reflns_point_group_measured_fraction_full 0.856
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.495
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 336 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.9(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2370
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0593
_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^)+(0.0399P)^2^+0.0267P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1324
_reflns_Friedel_coverage         0.481
_reflns_Friedel_fraction_full    0.660
_reflns_Friedel_fraction_max     0.660
_reflns_number_gt                1586
_reflns_number_total             2370
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00573_si_002.cif
_cod_data_source_block           lujt_0302
_cod_depositor_comments          'Adding full bibliography for 4032642.cif.'
_cod_original_cell_volume        1412.10(13)
_cod_database_code               4032642
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
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:
 C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), C2(H2A), C3(H3), C4(H4), C10(H10), C13(H13)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C15(H15A,H15B,H15C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_date_sample_data_collection 2017-03-03
_olex2_submission_special_instructions 'No special instructions were received'