Asymmetric Diels–Alder cycloadditions of benzofulvene-based 2,4-dienals via trienamine activation
Yue, Jing-Fei; Ran, Guang-Yao; Yang, Xing-Xing; Du, Wei; Chen, Ying-Chun; Organic Chemistry Frontiers 5 (2018) 2676–; doi:10.1039/C8QO00653A

data_1554377
_publ_section_title
;
 Asymmetric Diels--Alder cycloadditions of benzofulvene-based 2,4-dienals
 via trienamine activation
;
_journal_issue                   18
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2676
_journal_paper_doi               10.1039/C8QO00653A
_journal_volume                  5
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C36 H34 N O6'
_chemical_formula_sum            'C36 H34 N O6'
_chemical_formula_weight         576.64
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-07-07
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2018-07-01 deposited with the CCDC.
2018-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.3083(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0672(2)
_cell_length_b                   24.0508(5)
_cell_length_c                   11.3892(2)
_cell_measurement_reflns_used    15255
_cell_measurement_temperature    296.31(10)
_cell_measurement_theta_max      72.6400
_cell_measurement_theta_min      5.3540
_cell_volume                     3030.73(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      air
_diffrn_ambient_temperature      296.31(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
  1 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -57.0000 -150.0000 84

  2 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -77.0000  -30.0000 94

  3 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -38.0000  120.0000 88

  4 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -57.0000   90.0000 84

  5 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671 -125.0000   90.0000 67

  6 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -57.0000  -90.0000 84

  7 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -77.0000 -180.0000 94

  8 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -77.0000   60.0000 94

  9 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671 -125.0000  -90.0000 67

 10 omega  -33.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671    0.0000  -90.0000 138

 11 omega   40.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

 12 omega   40.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 58

 13 omega   38.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 14 omega   38.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

 15 omega   90.00  175.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  120.0000 85

 16 omega   39.00  109.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 70

 17 omega   39.00  109.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 70

 18 omega   40.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

 19 omega   70.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  150.0000 108

 20 omega   38.00  116.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 78

 21 omega   37.00  146.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  -30.0000 109

 22 omega   70.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -120.0000 108

 23 omega   39.00  109.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 70

 24 omega   38.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

 25 omega   38.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

 26 omega   40.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 58

 27 omega   39.00  109.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 70

 28 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   77.0000  -60.0000 95

 29 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   77.0000  150.0000 95

 30 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   57.0000   60.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1330644000
_diffrn_orient_matrix_UB_12      0.0186771000
_diffrn_orient_matrix_UB_13      0.0007890000
_diffrn_orient_matrix_UB_21      -0.0406363000
_diffrn_orient_matrix_UB_22      -0.0612693000
_diffrn_orient_matrix_UB_23      -0.0013283000
_diffrn_orient_matrix_UB_31      0.0035463000
_diffrn_orient_matrix_UB_32      -0.0006894000
_diffrn_orient_matrix_UB_33      0.1353462000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            33123
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.764
_diffrn_reflns_theta_min         5.350
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54408
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       block
_exptl_crystal_F_000             1220
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
;
 Flack x determined using 4958 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     783
_refine_ls_number_reflns         11836
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1081P)^2^+0.1285P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1450
_reflns_Friedel_coverage         0.932
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                11075
_reflns_number_total             11836
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00653a2.cif
_cod_data_source_block           4n
_cod_depositor_comments
;

2022-04-19
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C72 H68 N2 O12'
_cod_original_formula_weight         1153.28
_cod_original_formula_moiety         '2(C36 H34 N O6)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        3030.72(11)
_cod_database_code               1554377
_reflns_odcompleteness_completeness 99.89
_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:
 C00L(H00L), C00O(H00O), C00T(H00T), C00V(H00V), C00W(H00W), C010(H010)
2.b Secondary CH2 refined with riding coordinates:
 C00Y(H00A,H00B), C01B(H01F,H01G), C01Y(H01O,H01Y), C029(H02A,H02B)
2.c Aromatic/amide H refined with riding coordinates:
 C00R(H00R), C00Z(H00Z), C011(H011), C013(H013), C01A(H01A), C01C(H01C),
 C01D(H01H), C01E(H01I), C01G(H01K), C01J(H01J), C01K(H01L), C01L(H01M),
 C01N(H01N), C01P(H01P), C01Q(H01Q), C01R(H01R), C01S(H01S), C01T(H01T),
 C01U(H01U), C01V(H01V), C01W(H01W), C01X(H01X), C020(H020), C021(H021),
 C022(H022), C023(H023), C024(H024), C025(H025), C027(H027), C028(H028)
2.d Idealised Me refined as rotating group:
 C01O(H01B,H01D,H01E), C01Z(H01Z,H,HA), C026(H02L,H02M,H02N), C02A(H02O,H02P,
 H02Q), C02B(H02C,H02D,H02E), C02C(H02F,H02G,H02H), C02D(H02R,H02S,H02T),
 C02E(H02I,H02J,H02K)
;
_shelx_res_checksum              51574
_shelx_hkl_checksum              33759
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2017-07-07
_olex2_submission_special_instructions 'No special instructions were received'