Total Synthesis of (-)-Ambiguine P.
Xu, Jiasu; Rawal, Viresh H.; Journal of the American Chemical Society 141 (2019) 4820–4823; doi:10.1021/jacs.9b01739

data_4129025
_publ_section_title
;
 Total Synthesis of (-)-Ambiguine P.
;
_journal_issue                   12
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4820
_journal_page_last               4823
_journal_paper_doi               10.1021/jacs.9b01739
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C24 H31 N O'
_chemical_formula_sum            'C24 H31 N O'
_chemical_formula_weight         349.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-07-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.587(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.883(4)
_cell_length_b                   14.071(6)
_cell_length_c                   13.651(6)
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.06
_cell_measurement_theta_min      2.42
_cell_volume                     2013.6(14)
_computing_cell_refinement       'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX3 v.2015.9-0 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics
;
OLEX2: a complete structure solution, refinement and analysis program 
Dolomanov et al., 2009

Mercury: visualization and analysis of crystal structures
Macrae, et al., 2006

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann.
J. Appl. Cryst. (2009). 42, 339-341;

C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst. (2006). 39, 453-457.
;
_computing_publication_material
;
 APEX3 v.2015.5-2 (Bruker AXS Inc., 2015)
 OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'ShelXL (Sheldrick, 2018)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            CMOS
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1216
_diffrn_reflns_av_unetI/netI     0.0863
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            31216
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        25.106
_diffrn_reflns_theta_max         25.106
_diffrn_reflns_theta_min         2.423
_diffrn_source                   'micro-focus X-ray tube'
_diffrn_source_type              'INCOATEC ImuS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1259 before and 0.0713 after correction. 
The Ratio of minimum to maximum transmission is 0.8427. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.387
_exptl_crystal_size_mid          0.251
_exptl_crystal_size_min          0.114
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1754 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         6779
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0543
_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^)+(0.0832P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1494
_reflns_Friedel_coverage         0.854
_reflns_Friedel_fraction_full    0.912
_reflns_Friedel_fraction_max     0.912
_reflns_number_gt                4615
_reflns_number_total             6779
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b01739_si_002.cif
_cod_data_source_block           0632
_cod_original_cell_volume        2013.7(14)
_cod_database_code               4129025
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C18(H18), C32(H32), C33(H33), C42(H42)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C20(H20A,H20B), C37(H37A,H37B), C38(H38A,
 H38B), C44(H44A,H44B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C26(H26), C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C35(H35A,H35B,H35C), C36(H36A,
 H36B,H36C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C47(H47A,H47B,H47C),
 C48(H48A,H48B,H48C)
;
_shelx_res_checksum              98583
_shelx_hkl_checksum              41233
_olex2_submission_special_instructions 'No special instructions were received'