Synthesis of highly substituted 2-spiropiperidines.
Griggs, Samuel D.; Thompson, Nathan; Tape, Daniel T.; Fabre, Marie; Clarke, Paul A.; Organic & biomolecular chemistry 16 (2018) 6663–6674; doi:10.1039/c8ob01272e

data_7156345
_publ_section_title
;
 Synthesis of highly substituted 2-spiropiperidines.
;
_journal_issue                   36
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6663
_journal_page_last               6674
_journal_paper_doi               10.1039/c8ob01272e
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C17 H20 F N O4'
_chemical_formula_sum            'C17 H20 F N O4'
_chemical_formula_weight         321.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc1p0wxh
_audit_creation_date             2016-12-22
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2017-05-15 deposited with the CCDC.
2018-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.4481(15)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.44998(10)
_cell_length_b                   20.5679(3)
_cell_length_c                   23.9334(4)
_cell_measurement_reflns_used    4774
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      70.3970
_cell_measurement_theta_min      4.2810
_cell_volume                     3165.50(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9990
_diffrn_measured_fraction_theta_max 0.9990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -68.00 -33.00   1.00    6.00    --    0.00 -57.00-150.00   35
  2  \w    -22.00  20.00   1.00    6.00    --    0.00 -57.00-150.00   42
  3  \w      2.00  41.00   1.00    6.00    --    0.00  57.00-180.00   39
  4  \w      1.00  67.00   1.00   24.00    --   54.00 -37.00  90.00   66
  5  \w     38.00 116.00   1.00   24.00    --   54.00  57.00 -90.00   78
  6  \w     45.00 100.00   1.00   24.00    --   54.00-125.00-180.00   55
  7  \w     55.00 107.00   1.00   24.00    --   54.00  57.00  30.00   52
  8  \w     40.00 157.00   1.00   48.00    --  108.00  12.00  60.00  117
  9  \w     57.00 124.00   1.00   48.00    --  108.00 -50.00 -60.00   67
 10  \w     62.00 116.00   1.00   48.00    --  108.00-111.00-180.00   54
 11  \w     41.00 108.00   1.00   48.00    --  108.00-111.00 120.00   67
 12  \w     89.00 171.00   1.00   48.00    --  108.00  50.00 -90.00   82
 13  \w     51.00 109.00   1.00   48.00    --  108.00 -50.00  60.00   58
 14  \w    106.00 138.00   1.00   48.00    --  108.00 178.00 -30.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0372300000
_diffrn_orient_matrix_UB_12      -0.0031957000
_diffrn_orient_matrix_UB_13      0.0627467000
_diffrn_orient_matrix_UB_21      -0.2366192000
_diffrn_orient_matrix_UB_22      0.0025190000
_diffrn_orient_matrix_UB_23      -0.0148593000
_diffrn_orient_matrix_UB_31      -0.0063342000
_diffrn_orient_matrix_UB_32      -0.0747795000
_diffrn_orient_matrix_UB_33      -0.0031863000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11090
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         3.705
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.866
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
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    1.349
_exptl_crystal_description       block
_exptl_crystal_F_000             1360.0
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: isopropyl alcohol/ diethyl ether'
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.00031(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         5650
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0362
_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^)+(0.0366P)^2^+1.4194P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0912
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4757
_reflns_number_total             5650
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01272e2.cif
_cod_data_source_block           pac1626
_cod_depositor_comments          'Adding full bibliography for 7156345.cif.'
_cod_database_code               7156345
_chemical_oxdiff_formula         'C17 H20 F1 N1 O4'
_chemical_oxdiff_usercomment     'Sam Griggs SG-5-21'
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C2(H2), C5(H5), C19(H19), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C21(H21A,
 H21B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C15(H15), C16(H16), C29(H29), C30(H30), C32(H32), C33(H33)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C34(H34A,H34B,H34C)
;
_shelx_res_checksum              84711
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-12-21
_olex2_date_sample_submission    2016-12-13
_olex2_exptl_crystal_mounting_method 'oil on 75 micrometre micromount'
_olex2_submission_original_sample_id SG-5-21
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.158
_oxdiff_exptl_absorpt_empirical_full_min 0.890