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_4032389
_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      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-08-18
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.9603(18)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.1282(4)
_cell_length_b                   12.2400(2)
_cell_length_c                   25.3264(5)
_cell_measurement_reflns_used    15678
_cell_measurement_temperature    293
_cell_measurement_theta_max      73.1330
_cell_measurement_theta_min      4.0000
_cell_volume                     5872.5(2)
_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
_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 0.992
_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    -68.00  21.00   1.00    1.95    --  -43.29  57.00 -90.00   89
  2  \w     76.00 108.00   1.00    1.95    --   43.29 126.00-180.00   32
  3  \w     85.00 127.00   1.00    7.80    --  102.90  30.00-120.00   42
  4  \w     79.00 148.00   1.00    7.80    --  102.90  30.00 -30.00   69
  5  \w     96.00 156.00   1.00    7.80    --  102.90  45.00  60.00   60
  6  \w    100.00 133.00   1.00    7.80    --  102.90  45.00 120.00   33
  7  \w     85.00 157.00   1.00    7.79    --  102.90  77.00 150.00   72
  8  \w     91.00 117.00   1.00    1.95    --   43.29 126.00 120.00   26
  9  \w     34.00 117.00   1.00    7.79    --  102.90 -61.00 -60.00   83
 10  \w     29.00  97.00   1.00    7.79    --  102.90 -95.00 150.00   68
 11  \w   -107.00 -81.00   1.00    1.95    --  -43.29 -99.00-120.00   26
 12  \w   -119.00 -79.00   1.00    1.95    --  -43.29 -99.00-180.00   40
 13  \w     19.00  89.00   1.00    1.95    --   43.29  77.00-120.00   70
 14  \w     64.00 104.00   1.00    1.95    --   43.29  77.00 -60.00   40
 15  \w     27.00  90.00   1.00    1.95    --   43.29  57.00-180.00   63
 16  \w     21.00  74.00   1.00    1.95    --   43.29  57.00  60.00   53
 17  \w     72.00  98.00   1.00    7.79    --  102.90  77.00 150.00   26
 18  \w     76.00 117.00   1.00    7.79    --  102.90 125.00-150.00   41
 19  \w     71.00  96.00   1.00    7.79    --  102.90  77.00 120.00   25
 20  \w    130.00 158.00   1.00    7.79    --  102.90  77.00-180.00   28
 21  \w     80.00 106.00   1.00    7.79    --  102.90  45.00-150.00   26
 22  \w     83.00 146.00   1.00    7.79    --  102.90 125.00 -60.00   63
 23  \w     78.00 104.00   1.00    7.79    --  102.90  61.00-150.00   26
 24  \w    127.00 156.00   1.00    7.79    --  102.90  61.00-150.00   29
 25  \w     77.00 103.00   1.00    7.79    --  102.90  61.00-180.00   26
 26  \w     80.00 156.00   1.00    7.79    --  102.90  61.00  30.00   76
 27  \w     20.00  48.00   1.00    7.79    --  102.90 -95.00   0.00   28
 28  \w     72.00  97.00   1.00    7.79    --  102.90  77.00-180.00   25
 29  \w     78.00 104.00   1.00    7.79    --  102.90  61.00 150.00   26
 30  \w     80.00 106.00   1.00    7.79    --  102.90  45.00-180.00   26
 31  \w    111.00 138.00   1.00    7.79    --  102.90  77.00 120.00   27
 32  \w     95.00 132.00   1.00    7.79    --  102.90 125.00 -30.00   37
 33  \w     24.00  82.00   1.00    7.79    --  102.90 -15.00  60.00   58
;
_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      0.0602473000
_diffrn_orient_matrix_UB_12      -0.0820276000
_diffrn_orient_matrix_UB_13      0.0161385000
_diffrn_orient_matrix_UB_21      0.0160096000
_diffrn_orient_matrix_UB_22      -0.0025645000
_diffrn_orient_matrix_UB_23      -0.0579584000
_diffrn_orient_matrix_UB_31      0.0521933000
_diffrn_orient_matrix_UB_32      0.0954633000
_diffrn_orient_matrix_UB_33      0.0123551000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            27759
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.306
_diffrn_reflns_theta_min         3.524
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  0.897
_exptl_absorpt_correction_T_min  0.781
_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_density_diffrn    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             2368
_exptl_crystal_size_max          0.564
_exptl_crystal_size_mid          0.417
_exptl_crystal_size_min          0.207
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         5850
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0707P)^2^+2.5807P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1401
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4954
_reflns_number_total             5850
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00169_si_002.cif
_cod_data_source_block           compound_18b
_cod_depositor_comments
'Adding full bibliography for 4032384--4032390.cif.'
_cod_database_code               4032389
_chemical_oxdiff_formula         'C34 N4 O4 H32'
_reflns_odcompleteness_completeness 99.98
_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:
 C8(H8), C11(H11), C12(H12), C17(H17), C18(H18), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C22(H22A,H22B), C27(H27A,H27B), C28(H28A,H28B)
2.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)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-08-17
_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 1.913
_oxdiff_exptl_absorpt_empirical_full_min 0.405