A Two-Directional Synthesis of (+)-β-Isosparteine.
Al-Saffar, Firas M; Brown, Richard C. D.; Organic letters 19 (2017) 3502–3504; doi:10.1021/acs.orglett.7b01475

data_1546319
_publ_section_title
;
 A Two-Directional Synthesis of (+)-\b-Isosparteine.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3502
_journal_page_last               3504
_journal_paper_doi               10.1021/acs.orglett.7b01475
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H28 Cl N O4 S'
_chemical_formula_sum            'C20 H28 Cl N O4 S'
_chemical_formula_weight         413.94
_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   geom
_audit_creation_date             2015-06-23
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.06.08 svn.r3188 for OlexSys, GUI svn.r5059)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4385(7)
_cell_length_b                   17.461(2)
_cell_length_c                   19.3045(16)
_cell_measurement_reflns_used    3143
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.8930
_cell_measurement_theta_min      2.1530
_cell_volume                     2170.3(4)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega -109.00   15.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000  -54.0000 -150.0000 124

  2 omega  -49.00   20.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000   54.0000 -150.0000 69

  3 omega   52.00   62.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000   72.0000 -150.0000 10

  4 omega  -92.00  -64.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000  -72.0000   60.0000 28
;
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-VHF'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      0.1044802000
_diffrn_orient_matrix_UB_12      -0.0083615000
_diffrn_orient_matrix_UB_13      -0.0088471000
_diffrn_orient_matrix_UB_21      0.0232019000
_diffrn_orient_matrix_UB_22      0.0396917000
_diffrn_orient_matrix_UB_23      -0.0004191000
_diffrn_orient_matrix_UB_31      0.0263002000
_diffrn_orient_matrix_UB_32      -0.0015866000
_diffrn_orient_matrix_UB_33      0.0356709000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1294
_diffrn_reflns_av_unetI/netI     0.1638
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11375
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.699
_diffrn_reflns_theta_min         3.146
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       plate
_exptl_crystal_F_000             880
_exptl_crystal_preparation       'LDA, THF (-78degC)'
_exptl_crystal_recrystallization_method
'The material was recrystallised from chloroform by slow evaporation'
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.366
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.196
_refine_ls_abs_structure_details
;
 Flack x determined using 620 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         5336
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1958
_refine_ls_R_factor_gt           0.1323
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3192
_refine_ls_wR_factor_ref         0.3642
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_full    0.932
_reflns_Friedel_fraction_max     0.899
_reflns_number_gt                2937
_reflns_number_total             5336
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01475_si_005.cif
_cod_data_source_block           2015sot0035_r_100k
_cod_depositor_comments
'Adding full bibliography for 1546317--1546319.cif.'
_cod_database_code               1546319
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_reflns_odcompleteness_completeness 92.14
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.54
_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), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B),
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              67026
_shelx_hkl_checksum              33161
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_submission    2015-06-10
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id fals/7479/53.p3
_olex2_submission_special_instructions 'No special instructions were received'