Asymmetric Synthesis of 1-Substituted 2-Azaspiro[3.3]heptanes: An Important Motifs for Modern Drug Discovery.
Reddy, Leleti Rajender; Yogesh, Waman; Kallure, Priya; Swamy, Kumara; Begum, Zubeda; thumbar, Divya; Sharadsrikar, Kotturi; Chemical Communications  (2019) –; doi:10.1039/C9CC00863B

data_7123100
_publ_section_title
;
 Asymmetric Synthesis of 1-Substituted 2-Azaspiro[3.3]heptanes: An
 Important Motifs for Modern Drug Discovery.
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC00863B
_journal_year                    2019
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C14 H21 N O S2'
_chemical_formula_sum            'C14 H21 N O S2'
_chemical_formula_weight         283.44
_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
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc21f16r
_audit_creation_date             2018-10-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-08 deposited with the CCDC.    2019-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5013(8)
_cell_length_b                   12.0985(12)
_cell_length_c                   15.0956(17)
_cell_measurement_reflns_used    6816
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.05
_cell_measurement_theta_min      2.70
_cell_volume                     1552.6(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX-II'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12105
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.114
_diffrn_reflns_theta_max         25.114
_diffrn_reflns_theta_min         2.157
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.332
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/4 (Bruker,2014/4)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 1071 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2765
_refine_ls_number_restraints     61
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0652P)^2^+0.0844P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0944
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2626
_reflns_number_total             2765
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc00863b2.cif
_cod_data_source_block           sm_ird0257_0m
_cod_database_code               7123100
_shelx_shelxl_version_number     2018/1
_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. Restrained distances
 S2A-C12 \\sim S2B-C12
 with sigma of 0.02
 S2A-C14A \\sim S2B-C14B
 with sigma of 0.02
 C11A-C12 \\sim C11B-C12
 with sigma of 0.02
 C11A-C13A \\sim C11B-C13B
 with sigma of 0.02
 C13A-C14A \\sim C13B-C14B
 with sigma of 0.02
 S2A-C13A \\sim S2B-C13B
 with sigma of 0.04
 C11A-C14A \\sim C11B-C14B
 with sigma of 0.04
 C12-C13A \\sim C12-C13B
 with sigma of 0.04
 C12-C14A \\sim C12-C14B
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 S2A, S2B, C11A, C11B, C12, C13A, C13B, C14A, C14B
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
4. Others
 Fixed Sof: S2A(0.58654) S2B(0.41346) C11A(0.58654) H11A(0.58654)
 C13A(0.58654) H13A(0.58654) C14A(0.58654) H14A(0.58654) C11B(0.41346)
 H11B(0.41346) C13B(0.41346) H13B(0.41346) C14B(0.41346) H14B(0.41346)
5.a Ternary CH refined with riding coordinates:
 C1(H1)
5.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C8(H8A,H8B), C10(H10A,H10B)
5.c Aromatic/amide H refined with riding coordinates:
 C11A(H11A), C13A(H13A), C14A(H14A), C11B(H11B), C13B(H13B), C14B(H14B)
5.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              2777
_shelx_hkl_checksum              38249
_olex2_submission_special_instructions 'No special instructions were received'