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_4032388
_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         'C34 H32 N4 O4'
_chemical_formula_sum            'C34 H32 N4 O4'
_chemical_formula_weight         560.63
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-08-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                75.244(5)
_cell_angle_beta                 88.540(5)
_cell_angle_gamma                67.453(5)
_cell_formula_units_Z            2
_cell_length_a                   11.2044(7)
_cell_length_b                   11.5815(6)
_cell_length_c                   12.9947(8)
_cell_measurement_reflns_used    5573
_cell_measurement_temperature    293
_cell_measurement_theta_max      73.1020
_cell_measurement_theta_min      3.5180
_cell_volume                     1501.06(17)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 4.1600
_diffrn_detector_type            Titan
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.960
_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    -26.00  69.00   1.00    6.86    --   43.29 -57.00  60.00   95
  2  \w     28.00 141.00   1.00   27.42    --  102.90 -15.00 120.00  113
  3  \w     83.00 137.00   1.00   27.42    --  102.90  45.00 120.00   54
  4  \w    109.00 151.00   1.00   27.42    --  102.90  77.00 120.00   42
  5  \w     56.00 122.00   1.00   27.42    --  102.90 -45.00  60.00   66
  6  \w     85.00 110.00   1.00   27.42    --  102.90 -95.00 -30.00   25
  7  \w     76.00 109.00   1.00   27.42    --  102.90 -95.00 -90.00   33
  8  \w     72.00 122.00   1.00   27.42    --  102.90-126.00-150.00   50
  9  \w     87.00 128.00   1.00   27.42    --  102.90 -30.00-180.00   41
 10  \w     41.00  67.00   1.00   27.42    --  102.90 -95.00 -30.00   26
 11  \w     33.00 134.00   1.00   27.42    --  102.90 -77.00 -30.00  101
 12  \w     70.00  96.00   1.00   27.42    --  102.90 -95.00  90.00   26
 13  \w     32.00  69.00   1.00   27.42    --  102.90-132.00 140.00   37
 14  \w     31.00 120.00   1.00   27.42    --  102.90 -30.00 -60.00   89
 15  \w     34.00 122.00   1.00   27.42    --  102.90 -61.00-180.00   88
 16  \w     18.00 113.00   1.00    6.86    --   43.29  57.00-150.00   95
 17  \w    -71.00  21.00   1.00    6.86    --  -43.29  77.00 -30.00   92
;
_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      0.0012385000
_diffrn_orient_matrix_UB_12      0.0345697000
_diffrn_orient_matrix_UB_13      -0.1225095000
_diffrn_orient_matrix_UB_21      0.1443176000
_diffrn_orient_matrix_UB_22      -0.0908234000
_diffrn_orient_matrix_UB_23      0.0105817000
_diffrn_orient_matrix_UB_31      -0.0384732000
_diffrn_orient_matrix_UB_32      -0.1134472000
_diffrn_orient_matrix_UB_33      -0.0028388000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10693
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.252
_diffrn_reflns_theta_min         3.529
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  0.909
_exptl_absorpt_correction_T_min  0.785
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
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    1.240
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.628
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.165
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         5785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0883
_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^)+(0.1771P)^2^+0.2214P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2712
_refine_ls_wR_factor_ref         0.2972
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4132
_reflns_number_total             5785
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00169_si_002.cif
_cod_data_source_block           compound_18a
_cod_depositor_comments
'Adding full bibliography for 4032384--4032390.cif.'
_cod_original_cell_volume        1501.08(16)
_cod_database_code               4032388
_chemical_oxdiff_formula         'C34 N4 O4 H32'
_reflns_odcompleteness_completeness 99.68
_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(H19C)=Sof(H19D)=Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=1-FVAR(1)
 Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C8(H8), C12(H12), C14(H14), C21(H21), C22(H22), C23(H23)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C19(H19A,H19B), C19(H19C,H19D), C27(H27A,H27B), C28(H28A,H28B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C30(H30), C31(H31), C32(H32), C33(H33),
 C34(H34)
3.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C25(H25A,H25B,H25C), C20(H20A,H20B,H20C), C20A(H20D,H20E,
 H20F)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-08-03
_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 3.127
_oxdiff_exptl_absorpt_empirical_full_min 0.242