Dynamic resolution of 2-cyclohexylidene acetaldehydes through organocatalytic dienamine [4+2] cycloaddition
Jakob Blom; Tore Kiilerich Johansen; Frank Jensen; Karl Anker Jorgensen; Chem.Commun. 52 (2016) 7153–; doi:

data_7119004
_publ_section_title
;
 Dynamic resolution of 2-cyclohexylidene acetaldehydes through
 organocatalytic dienamine [4+2] cycloaddition
;
_journal_name_full               Chem.Commun.
_journal_page_first              7153
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H28 Br N3 O3'
_chemical_formula_sum            'C25 H28 Br N3 O3'
_chemical_formula_weight         498.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_date             2016-03-03
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-03-03 deposited with the CCDC.
2016-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.284(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.064(3)
_cell_length_b                   8.502(2)
_cell_length_c                   13.718(4)
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    100
_cell_measurement_theta_max      21.55
_cell_measurement_theta_min      2.23
_cell_volume                     1154.9(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.9918
_diffrn_measured_fraction_theta_max 0.9918
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Ag K\a'
_diffrn_radiation_wavelength     0.56086
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29092
_diffrn_reflns_theta_full        22.2764
_diffrn_reflns_theta_max         22.28
_diffrn_reflns_theta_min         1.19
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.977
_exptl_absorpt_correction_T_max  0.7447
_exptl_absorpt_correction_T_min  0.5659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1387 before and 0.0769 after correction.
The Ratio of minimum to maximum transmission is 0.7599.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.4331
_exptl_crystal_description       block
_exptl_crystal_F_000             516.4725
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.9934
_refine_diff_density_min         -0.7817
_refine_diff_density_rms         0.1128
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.029(11)
_refine_ls_d_res_high            0.7398
_refine_ls_d_res_low             13.4979
_refine_ls_goodness_of_fit_ref   1.0030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    45
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5929
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0030
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0637P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1016
_reflns_Friedel_coverage         0.989
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              18
_reflns_limit_l_min              -18
_reflns_number_gt                5239
_reflns_number_total             5929
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c6cc02019d2.cif
_cod_data_source_block           2015_11_17_0m
_cod_original_cell_volume        1154.9(5)
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_database_code               7119004
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C017(H017), C031(H031)
2.b Secondary CH2 refined with riding coordinates:
 C019(H01d,H01e), C022(H02a,H02b), C023(H02c,H02d), C025(H02e,H02f), C029(H02j,
 H02k)
2.c Aromatic/amide H refined with riding coordinates:
 C018(H018), C012(H012), C010(H010), N007(H007), C0AA(H0AA), C026(H026),
 C027(H027)
2.d Idealised Me refined as rotating group:
 C008(H00a,H00b,H00c), C015(H01a,H01b,H01c), C028(H02g,H02h,H02i)
;
_olex2_submission_special_instructions 'No special instructions were received'