The synthesis and structure of chiral enamine N-oxides
I. A. O'Neil; M. McConville; K. Zhou; C. Brooke; C. M. Robertson; N. G. Berry; Chem.Commun. 50 (2014) 7336–; doi:10.1039/C3CC47928E

data_7114619
_publ_section_title
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 The synthesis and structure of chiral enamine N-oxides
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_journal_name_full               Chem.Commun.
_journal_page_first              7336
_journal_paper_doi               10.1039/C3CC47928E
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C25 H29 N O6'
_chemical_formula_sum            'C25 H29 N O6'
_chemical_formula_weight         439.49
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-09-25
_audit_creation_method
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Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.252(2)
_cell_length_b                   10.869(2)
_cell_length_c                   40.512(9)
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.27
_cell_measurement_theta_min      2.23
_cell_volume                     4514.2(16)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
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O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            26084
_diffrn_reflns_theta_full        26.33
_diffrn_reflns_theta_max         26.33
_diffrn_reflns_theta_min         1.94
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6760
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
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SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0930 before and 0.0496 after correction.
The Ratio of minimum to maximum transmission is 0.9060.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.0(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     586
_refine_ls_number_reflns         9101
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0478P)^2^+0.6874P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0874
_reflns_number_gt                8480
_reflns_number_total             9101
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc47928e2.cif
_cod_data_source_block           frm_0m_1
_cod_original_cell_volume        4514.4(16)
_cod_database_code               7114619
_olex2_refinement_description
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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:
 C40(H40), C33(H33)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C25(H25A,H25B), C39(H39A,H39B), C49(H49A,H49B), C31(H31A,
 H31B), C43(H43A,H43B), C48(H48A,H48B), C59(H59A,H59B), C10(H10A,H10B), C1(H1A,
 H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C24(H24), C27(H27), C32(H32), C46(H46), C53(H53), C56(H56),
 C58(H58), C60(H60), C62(H62), C22(H22), C28(H28), C29(H29), C35(H35), C37(H37),
  C41(H41), C45(H45), C47(H47), C52(H52), C54(H54), C55(H55), C3(H3)
2.d Idealised Me refined as rotating group:
 C64(H64A,H64B,H64C), C51(H51A,H51B,H51C), C63(H63A,H63B,H63C), C2(H2A,H2B,H2C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
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