Synthesis of highly functionalized [3]dendralenes and their Diels-Alder reaction displaying unexpected regioselectivity
Naidu, Gonna Somu; Singh, Rekha; Kumar, Mukesh; Ghosh, Sunil Kumar; RSC Adv.  (2016) –; doi:10.1039/C6RA01729K

data_7224747
_publ_section_title
;
 Synthesis of highly functionalized [3]dendralenes and their Diels-Alder
 reaction displaying unexpected regioselectivity
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA01729K
_journal_year                    2016
_chemical_formula_moiety         'C29 H28 O3'
_chemical_formula_sum            'C29 H28 O3'
_chemical_formula_weight         424.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-05-30
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_audit_update_record
;
2015-09-28 deposited with the CCDC.
2016-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.128(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4846(6)
_cell_length_b                   15.8614(8)
_cell_length_c                   14.7350(8)
_cell_measurement_reflns_used    2956
_cell_measurement_temperature    293
_cell_measurement_theta_max      69.7000
_cell_measurement_theta_min      3.0450
_cell_volume                     2419.4(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 8.3200
_diffrn_measured_fraction_theta_full 0.9947
_diffrn_measured_fraction_theta_max 0.9780
_diffrn_measurement_details
;
  1 omega   63.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -180.0000 36

  2 omega   33.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000   90.0000 56

  3 omega -152.00 -126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -54.7289 -116.0000 -137.0000 26

  4 omega   75.00  148.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.7289  126.0000  -30.0000 73

  5 omega   23.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.7289 -126.0000  -60.0000 27

  6 omega   68.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.7289 -126.0000  -60.0000 54

  7 omega  -30.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.7289   30.0000   60.0000 77

  8 omega   60.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.7289   30.0000   60.0000 89

  9 omega   19.00  157.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -92.0000 -150.0000 138

 10 omega  119.00  154.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577   50.0000  -30.0000 35

 11 omega   36.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  178.0000 -120.0000 115

 12 omega   66.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577   50.0000  -30.0000 36

 13 omega   31.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -38.0000  -60.0000 25

 14 omega   44.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -25.0000   30.0000 28

 15 omega   51.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -50.0000 -150.0000 30

 16 omega   14.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -38.0000 -150.0000 36

 17 omega   13.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -38.0000   30.0000 53

 18 omega   46.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -25.0000  -30.0000 26

 19 omega   10.00   41.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -25.0000   30.0000 31
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Titan'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1440976000
_diffrn_orient_matrix_UB_12      -0.0048186000
_diffrn_orient_matrix_UB_13      0.0093663000
_diffrn_orient_matrix_UB_21      0.0013352000
_diffrn_orient_matrix_UB_22      -0.0957886000
_diffrn_orient_matrix_UB_23      -0.0169852000
_diffrn_orient_matrix_UB_31      0.0370685000
_diffrn_orient_matrix_UB_32      -0.0151986000
_diffrn_orient_matrix_UB_33      0.1041273000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8529
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.930
_diffrn_reflns_theta_min         4.123
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.585
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.165
_exptl_crystal_description       plate
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.108
_refine_diff_density_rms         0.025
_refine_ls_extinction_coef       0.0036(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4488
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0692P)^2^+0.1385P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1393
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3173
_reflns_number_total             4488
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra01729k2.cif
_cod_data_source_block           skg1
_cod_database_code               7224747
_chemical_oxdiff_formula         C29O3H28
_reflns_odcompleteness_completeness 99.47
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H10C)=Sof(H10D)=Sof(C11A)=Sof(H11D)=Sof(H11E)=Sof(H11F)=1-FVAR(1)
 Sof(H10A)=Sof(H10B)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(H11C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C10(H10A,H10B), C10(H10C,H10D)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C28(H28), C22(H22), C17(H17), C25(H25), C27(H27), C6(H6),
 C5(H5), C24(H24), C18(H18), C21(H21), C20(H20), C1(H1), C2(H2), C19(H19)
3.c X=CH2 refined with riding coordinates:
 C13(H13A,H13B)
3.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C11(H11A,H11B,H11C), C11A(H11D,H11E,H11F)
;
_shelxl_version_number           2013-4