Tuning the Stability and the Reactivity of Substituted [3]Dendralenes for Quick Access to Diverse Copiously Functionalized Fused Polycycles with Step and Atom Economy.
Naidu, Gonna Somu; Singh, Rekha; Kumar, Mukesh; Ghosh, Sunil K.; The Journal of organic chemistry 82 (2017) 3648–3658; doi:10.1021/acs.joc.7b00169

data_4032386
_publ_section_title
;
 Tuning the Stability and the Reactivity of Substituted [3]Dendralenes for
 Quick Access to Diverse Copiously Functionalized Fused Polycycles with
 Step and Atom Economy.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3648
_journal_page_last               3658
_journal_paper_doi               10.1021/acs.joc.7b00169
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C27 H27 N3 O6'
_chemical_formula_sum            'C27 H27 N3 O6'
_chemical_formula_weight         489.51
_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
_audit_creation_date             2016-06-02
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 116.342(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.7281(4)
_cell_length_b                   10.29860(17)
_cell_length_c                   16.3055(4)
_cell_measurement_reflns_used    8969
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.7450
_cell_measurement_theta_min      5.2140
_cell_volume                     2517.36(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 4.1600
_diffrn_detector_type            Titan
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     22.00 112.00   1.00    1.00    --   43.29  57.00 120.00   90
  2  \w     94.00 120.00   1.00    3.00    --  102.90  61.00  90.00   26
  3  \w    125.00 157.00   1.00    3.00    --  102.90  61.00  90.00   32
  4  \w     87.00 156.00   1.00    3.00    --  102.90  30.00 -30.00   69
  5  \w     91.00 117.00   1.00    1.00    --   43.29 126.00-180.00   26
  6  \w     71.00 101.00   1.00    3.00    --  102.90  77.00 -90.00   30
  7  \w     76.00 153.00   1.00    3.00    --  102.90  30.00 -90.00   77
  8  \w     81.00 151.00   1.00    3.00    --  102.90  30.00-150.00   70
  9  \w     67.00 114.00   1.00    1.00    --   43.29  38.00 -90.00   47
 10  \w     36.00 115.00   1.00    3.00    --  102.90 -61.00  60.00   79
 11  \w     30.00 126.00   1.00    3.00    --  102.90 -30.00 -60.00   96
 12  \w     77.00 112.00   1.00    3.00    --  102.90  61.00 120.00   35
 13  \w     72.00 130.00   1.00    3.00    --  102.90 126.00  90.00   58
 14  \w     35.00 122.00   1.00    3.00    --  102.90 -30.00  60.00   87
 15  \w     33.00 131.00   1.00    3.00    --  102.90 -77.00 -60.00   98
 16  \w    -64.00   7.00   1.00    1.00    --  -43.29  57.00 -60.00   71
 17  \w   -102.00 -19.00   1.00    1.00    --  -43.29 -38.00-150.00   83
 18  \w   -110.00 -85.00   1.00    1.00    --  -43.29 -99.00-120.00   25
 19  \w   -109.00 -75.00   1.00    1.00    --  -43.29-126.00  30.00   34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Titan'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0970928000
_diffrn_orient_matrix_UB_12      0.0459316000
_diffrn_orient_matrix_UB_13      0.0549294000
_diffrn_orient_matrix_UB_21      0.0317852000
_diffrn_orient_matrix_UB_22      -0.1079970000
_diffrn_orient_matrix_UB_23      -0.0440300000
_diffrn_orient_matrix_UB_31      -0.0111213000
_diffrn_orient_matrix_UB_32      0.0926343000
_diffrn_orient_matrix_UB_33      -0.0785357000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18194
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.290
_diffrn_reflns_theta_min         2.948
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.761
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.292
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4983
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0552
_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^)+(0.0840P)^2^+0.6619P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1552
_refine_ls_wR_factor_ref         0.1729
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3866
_reflns_number_total             4983
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00169_si_002.cif
_cod_data_source_block           compound_6
_cod_depositor_comments
'Adding full bibliography for 4032384--4032390.cif.'
_cod_original_cell_volume        2517.35(11)
_cod_database_code               4032386
_chemical_oxdiff_formula         'C27 H27 N3 O6'
_reflns_odcompleteness_completeness 99.90
_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:
 C18(H18), C8(H8), C17(H17), C23(H23), C24(H24), C15(H15), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C7(H7), C3(H3)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C20(H20A,H20B,H20C), C27(H27A,H27B,H27C), C12(H12A,H12B,
 H12C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-03-01
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.232
_oxdiff_exptl_absorpt_empirical_full_min 0.394