Bidirectional Synthesis of Di- tert-butyl (2 S,6 S,8 S)- and (2 R,6 R,8 R)-1,7-Diazaspiro[5.5]undecane-2,8-dicarboxylate and Related Spirodiamines.
Almond-Thynne, Joshua; Han, Jiaxu; White, Andrew J. P.; Polyzos, Anastasios; Parsons, Philip J.; Barrett, Anthony G. M.; The Journal of organic chemistry 83 (2018) 6783–6787; doi:10.1021/acs.joc.8b00794

data_4035818
_publ_section_title
;
 Bidirectional Synthesis of Di- tert-butyl (2 S,6 S,8 S)- and (2 R,6 R,8
 R)-1,7-Diazaspiro[5.5]undecane-2,8-dicarboxylate and Related
 Spirodiamines.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6783
_journal_page_last               6787
_journal_paper_doi               10.1021/acs.joc.8b00794
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C19 H34 N2 O4'
_chemical_formula_sum            'C19 H34 N2 O4'
_chemical_formula_weight         354.48
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1647(7)
_cell_length_b                   11.6691(7)
_cell_length_c                   16.6362(11)
_cell_measurement_reflns_used    920
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.1570
_cell_measurement_theta_min      4.8050
_cell_volume                     2167.4(2)
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_collection       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.4115
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Agilent Xcalibur PX Ultra A'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0822
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4773
_diffrn_reflns_point_group_measured_fraction_full 0.846
_diffrn_reflns_point_group_measured_fraction_max 0.802
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.676
_diffrn_reflns_theta_min         4.629
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.608
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_diffrn    1.086
_exptl_crystal_description       tablets
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
; 
 Flack x determined using 452 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.7(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3510
_refine_ls_number_restraints     94
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0681
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0744P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1610
_refine_ls_wR_factor_ref         0.1985
_reflns_Friedel_coverage         0.479
_reflns_Friedel_fraction_full    0.659
_reflns_Friedel_fraction_max     0.601
_reflns_number_gt                2037
_reflns_number_total             3510
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00794_si_002.cif
_cod_data_source_block           34
_cod_database_code               4035818
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              80046
_shelx_hkl_checksum              83823