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_7224749
_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         'C34 H32 Br N O5'
_chemical_formula_sum            'C34 H32 Br N O5'
_chemical_formula_weight         614.51
_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     iterative
_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                 93.631(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0988(11)
_cell_length_b                   27.6314(14)
_cell_length_c                   8.4212(5)
_cell_measurement_reflns_used    2699
_cell_measurement_temperature    293
_cell_measurement_theta_max      68.4150
_cell_measurement_theta_min      3.1930
_cell_volume                     3041.8(3)
_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
;
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
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 8.3200
_diffrn_measured_fraction_theta_full 0.9969
_diffrn_measured_fraction_theta_max 0.9768
_diffrn_measurement_details
;
  1 omega  -50.00    6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000 -180.0000 56

  2 omega   36.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000 -180.0000 66

  3 omega  -63.00   38.00   1.0000    2.6200
omega____ theta____ kappa____ phi______ frames
    -      -54.7289   30.0000  120.0000 101

  4 omega -110.00  -81.00   1.0000    2.6200
omega____ theta____ kappa____ phi______ frames
    -      -54.7289  -95.0000 -150.0000 29

  5 omega -114.00  -80.00   1.0000    2.6200
omega____ theta____ kappa____ phi______ frames
    -      -54.7289  -95.0000 -180.0000 34

  6 omega  123.00  157.00   1.0000    2.6200
omega____ theta____ kappa____ phi______ frames
    -       54.7289  126.0000  -90.0000 34

  7 omega  -36.00  101.00   1.0000    2.6200
omega____ theta____ kappa____ phi______ frames
    -       54.7289  -77.0000 -180.0000 137

  8 omega   12.00   58.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -25.0000  -30.0000 46

  9 omega   13.00  134.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -64.0000   60.0000 121

 10 omega   18.00   84.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577 -112.0000 -120.0000 66

 11 omega   21.00   68.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -25.0000 -150.0000 47

 12 omega   17.00   68.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -38.0000  -90.0000 51

 13 omega   70.00  111.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577 -112.0000 -150.0000 41

 14 omega  118.00  148.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577   64.0000 -150.0000 30

 15 omega   18.00   48.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577 -112.0000 -150.0000 30

 16 omega   38.00   64.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -38.0000  -60.0000 26

 17 omega   10.00   67.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4577  -38.0000   90.0000 57
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Titan'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0249670000
_diffrn_orient_matrix_UB_12      -0.0116738000
_diffrn_orient_matrix_UB_13      0.1772162000
_diffrn_orient_matrix_UB_21      0.1151240000
_diffrn_orient_matrix_UB_22      0.0044193000
_diffrn_orient_matrix_UB_23      -0.0250429000
_diffrn_orient_matrix_UB_31      -0.0041270000
_diffrn_orient_matrix_UB_32      0.0543004000
_diffrn_orient_matrix_UB_33      0.0400193000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10305
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.246
_diffrn_reflns_theta_min         3.199
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.179
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69416
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       needle
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.725
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0008(3)
_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   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         5660
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1130
_refine_ls_R_factor_gt           0.0787
_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^)+(0.1398P)^2^+0.3552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2324
_refine_ls_wR_factor_ref         0.2820
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3268
_reflns_number_total             5660
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra01729k2.cif
_cod_data_source_block           skg2_4
_cod_original_cell_volume        3041.8(4)
_cod_database_code               7224749
_chemical_oxdiff_formula         'C34 H32 Br N O5'
_reflns_odcompleteness_completeness 99.69
_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:
 C7(H7), C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C10(H10A,H10B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C27(H27), C5(H5), C29(H29), C26(H26), C30(H30), C3(H3), C6(H6), C33(H33),
 C22(H22), C32(H32), C25(H25), C23(H23), C24(H24), C2(H2)
2.d Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C15(H15A,H15B,H15C), C18(H18A,H18B,H18C)
;
_shelxl_version_number           2013-4