Enantioselective desymmetrization of prochiral 1,3-dinitropropanes via organocatalytic allylic alkylation
Soumya Jyoti Singha Roy; Santanu Mukherjee; Chem.Commun. 50 (2013) 121–; doi:10.1039/c3cc47645f

data_7110169
_publ_section_title
;
 Enantioselective desymmetrization of prochiral 1,3-dinitropropanes via
 organocatalytic allylic alkylation
;
_journal_name_full               Chem.Commun.
_journal_page_first              121
_journal_paper_doi               10.1039/c3cc47645f
_journal_volume                  50
_journal_year                    2013
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C19 H19 Cl N2 O'
_chemical_formula_sum            'C19 H19 Cl N2 O'
_chemical_formula_weight         326.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2013-09-20
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.437(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   75.874(8)
_cell_length_b                   5.7768(7)
_cell_length_c                   7.7098(8)
_cell_measurement_reflns_used    3074
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      17.66
_cell_measurement_theta_min      2.68
_cell_volume                     3376.2(6)
_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
;
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
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.972
_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  0.0678
_diffrn_reflns_av_unetI/netI     0.1045
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       92
_diffrn_reflns_limit_h_min       -92
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            20336
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         1.074
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1328 before and 0.0652 after correction.
The Ratio of minimum to maximum transmission is 0.8455.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             1377.66
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1061 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.05(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.860
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         6160
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.860
_refine_ls_R_factor_all          0.1369
_refine_ls_R_factor_gt           0.0569
_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^)+(0.1000P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1712
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.913
_reflns_Friedel_fraction_max     0.877
_reflns_number_gt                3233
_reflns_number_total             6160
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3cc47645f.txt
_cod_data_source_block           6
_cod_original_cell_volume        3376.2(7)
_cod_database_code               7110169
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H6 of C6, H7 of C7, H8 of C8, H2 of C2, H1A of C1A, H1B of C1B, H21 of C21,
  H22 of C22, H24 of C24, H25 of C25, {H26A,H26B} of C26, H28 of C28, H29 of
  C29, H30 of C30, {H31A,H31B} of C31, {H34A,H34B} of C34, H35 of C35, H36 of
  C36, H37 of C37, H38 of C38, H9 of C9, H11 of C11, H13 of C13, H14 of C14,
  H15 of C15, {H16A,H16B} of C16, H17 of C17, H18 of C18, {H19A,H19B} of C19,
  {H3A,H3B} of C3
 At 1.5 times of:
  H3 of O3, H1 of O1
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C24(H24), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C16(H16A,H16B), C19(H19A,H19B), C26(H26A,H26B), C31(H31A,H31B),
 C34(H34A,H34B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C7(H7), C11(H11), C13(H13), C14(H14), C15(H15), C17(H17),
 C18(H18), C1A(H1A), C1B(H1B), C21(H21), C22(H22), C28(H28), C29(H29), C30(H30),
  C35(H35), C36(H36), C37(H37), C38(H38)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3)
;
_shelxl_version_number           2013-2