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_7224750
_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         'C26 H27 N O4'
_chemical_formula_sum            'C26 H27 N O4'
_chemical_formula_weight         417.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-09-16
_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                 109.305(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7213(14)
_cell_length_b                   12.0482(10)
_cell_length_c                   13.0935(10)
_cell_measurement_reflns_used    2518
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.0010
_cell_measurement_theta_min      3.6710
_cell_volume                     2191.8(4)
_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
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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_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
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.3200
_diffrn_measured_fraction_theta_full 0.9954
_diffrn_measured_fraction_theta_max 0.7006
_diffrn_measurement_details
;
  1 omega  -62.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -150.0000 27

  2 omega  -74.00  -46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -180.0000 28

  3 omega  -78.00  -40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000    0.0000 38

  4 omega -154.00 -127.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -54.7289  -95.0000 -180.0000 27

  5 omega -149.00  -98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -54.7289  -95.0000   90.0000 51

  6 omega  -46.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.7289  -77.0000   30.0000 130

  7 omega  -45.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.7289  -30.0000   60.0000 110

  8 omega   59.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577   77.0000  120.0000 92

  9 omega   48.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  178.0000 -150.0000 26

 10 omega   11.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -38.0000   60.0000 45

 11 omega   38.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -25.0000 -120.0000 25

 12 omega  104.00  138.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  178.0000 -150.0000 34

 13 omega    7.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577 -112.0000   60.0000 95

 14 omega   80.00  150.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577   64.0000 -120.0000 70

 15 omega    9.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -50.0000   30.0000 67

 16 omega   41.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -38.0000  -60.0000 29

 17 omega   61.00  152.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577   64.0000 -150.0000 91
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Titan'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1017423000
_diffrn_orient_matrix_UB_12      -0.0415235000
_diffrn_orient_matrix_UB_13      -0.0645515000
_diffrn_orient_matrix_UB_21      0.0184378000
_diffrn_orient_matrix_UB_22      -0.1070909000
_diffrn_orient_matrix_UB_23      0.0681059000
_diffrn_orient_matrix_UB_31      -0.0398959000
_diffrn_orient_matrix_UB_32      0.0563600000
_diffrn_orient_matrix_UB_33      0.0817629000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7718
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.164
_diffrn_reflns_theta_min         3.181
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67603
_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            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0033(5)
_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   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4085
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0524
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0880P)^2^+0.2578P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1723
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2835
_reflns_number_total             4085
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra01729k2.cif
_cod_data_source_block           rekha3_2
_cod_database_code               7224750
_chemical_oxdiff_formula         'C26 H27 N O4'
_reflns_odcompleteness_completeness 99.54
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C8(H8), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C3(H3), C7(H7), C22(H22), C6(H6), C4(H4A), C23(H23), C26(H26),
 C25(H25), C24(H24)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelxl_version_number           2013-4