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_7119005
_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 .
_chemical_formula_moiety         'C30 H27 N3 O4'
_chemical_formula_sum            'C30 H27 N3 O4'
_chemical_formula_weight         493.57
_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                 99.955(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.983(3)
_cell_length_b                   10.976(3)
_cell_length_c                   16.961(4)
_cell_measurement_reflns_used    9865
_cell_measurement_temperature    100
_cell_measurement_theta_max      21.60
_cell_measurement_theta_min      2.25
_cell_volume                     2380.6(10)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9814
_diffrn_measured_fraction_theta_max 0.9814
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Ag K\a'
_diffrn_radiation_wavelength     0.56086
_diffrn_reflns_av_R_equivalents  0.0841
_diffrn_reflns_av_unetI/netI     0.0819
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            34349
_diffrn_reflns_theta_full        21.6634
_diffrn_reflns_theta_max         21.66
_diffrn_reflns_theta_min         0.96
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.058
_exptl_absorpt_correction_T_max  0.7447
_exptl_absorpt_correction_T_min  0.4988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1494 before and 0.0718 after correction.
The Ratio of minimum to maximum transmission is 0.6698.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.3770
_exptl_crystal_description       block
_exptl_crystal_F_000             1040.1491
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.3738
_refine_diff_density_min         -0.3292
_refine_diff_density_rms         0.0696
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.0(10)
_refine_ls_d_res_high            0.7597
_refine_ls_d_res_low             16.7058
_refine_ls_goodness_of_fit_ref   1.0081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    94
_refine_ls_number_parameters     670
_refine_ls_number_reflns         11189
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0081
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0519P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.1000
_reflns_Friedel_coverage         0.973
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              22
_reflns_limit_l_min              -22
_reflns_number_gt                9472
_reflns_number_total             11189
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c6cc02019d2.cif
_cod_data_source_block           2016_02_17B
_cod_original_cell_volume        2380.6(9)
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_database_code               7119005
_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:
 C00P(H00P), C019(H019), C01B(H01d), C01S(H1aa)
2.b Secondary CH2 refined with riding coordinates:
 C00X(H00a,H00b), C010(H01n,H01o), C017(H01a,H01b), C01J(H01e,H01f), C01N(H01u,
 H01v), C01O(H01y,H)
2.c Aromatic/amide H refined with riding coordinates:
 C00M(H00M), C00O(H00O), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W),
 C00Z(H00Z), C012(H012), C013(H013), C014(H014), C016(H016), C018(H018),
 C01A(H01c), C01C(H01s), C01G(H01t), C01M(H01M), C01P(H01z), C01Q(H01),
 C01R(H0aa), C01U(H2aa), C01V(H3aa), C01W(H01W), C01X(H01X), C020(H020),
 C021(H021), C022(H022)
2.d Idealised Me refined as rotating group:
 C015(H01p,H01q,H01r), C01L(H01g,H01h,H01i), C01Y(H4aa,Ha,Hb), C01Z(H01j,H01k,
 H01l)
;
_olex2_submission_special_instructions 'No special instructions were received'