(-)-Cytisine: Access to a stereochemically defined and functionally flexible piperidine scaffold.
Niwetmarin, Worawat; Rego Campello, Hugo; Sparkes, Hazel A.; Aggarwal, Varinder K.; Gallagher, Timothy; Organic & biomolecular chemistry 16 (2018) 5823–5832; doi:10.1039/c8ob01456f

data_7156329
_publ_section_title
;
 (-)-Cytisine: Access to a stereochemically defined and functionally
 flexible piperidine scaffold.
;
_journal_issue                   32
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5823
_journal_page_last               5832
_journal_paper_doi               10.1039/c8ob01456f
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H30 N2 O7'
_chemical_formula_sum            'C21 H30 N2 O7'
_chemical_formula_weight         422.47
_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             2015-10-23
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2018-04-27 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5893(15)
_cell_length_b                   11.638(2)
_cell_length_c                   22.452(4)
_cell_measurement_reflns_used    9741
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.377
_cell_measurement_theta_min      3.938
_cell_volume                     2244.4(7)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker Pt135 CCD area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker Mircostar Rotating anode'
_diffrn_measurement_device_type  'Rotating anode'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            40771
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_min         3.938
_diffrn_source                   'micro-focus rotating anode'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.3278
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1713 before and 0.1038 after correction.
The Ratio of minimum to maximum transmission is 0.4354.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0540P)^2^+0.4170P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0899
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3852
_reflns_number_total             3943
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01456f2.cif
_cod_data_source_block           31
_cod_depositor_comments
'Adding full bibliography for 7156327--7156329.cif.'
_cod_database_code               7156329
_shelxl_version_number           2013-4
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C19(H19A,H19B,H19C),
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              18687
_shelx_hkl_checksum              23977
_olex2_submission_special_instructions 'No special instructions were received'