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_4032387
_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         'C30 H28 N2 O6'
_chemical_formula_sum            'C30 H28 N2 O6'
_chemical_formula_weight         512.54
_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             2017-01-03
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.255(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5019(14)
_cell_length_b                   21.1909(18)
_cell_length_c                   10.0757(15)
_cell_measurement_reflns_used    3870
_cell_measurement_temperature    293
_cell_measurement_theta_max      67.7000
_cell_measurement_theta_min      3.5620
_cell_volume                     2658.1(5)
_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 0.997
_diffrn_measured_fraction_theta_max 0.968
_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    -65.00  25.00   1.00    2.81    --  -42.79  57.00-180.00   90
  2  \w     19.00  79.00   1.00    2.81    --   42.79-126.00  30.00   60
  3  \w     43.00 120.00   1.00   11.23    --  102.90 -61.00  90.00   77
  4  \w     98.00 129.00   1.00   11.23    --  102.90 -30.00  30.00   31
  5  \w     77.00 156.00   1.00   11.23    --  102.90  30.00   0.00   79
  6  \w     85.00 145.00   1.00   11.23    --  102.90  45.00 120.00   60
  7  \w     42.00  69.00   1.00   18.00    --  102.90 -30.00  30.00   27
  8  \w     44.00 134.00   1.00   18.00    --  102.90 -77.00 -30.00   90
  9  \w     78.00 153.00   1.00   18.00    --  102.90  45.00-150.00   75
 10  \w   -114.00 -87.00   1.00    3.00    --  -42.79 -99.00-180.00   27
 11  \w   -121.00 -93.00   1.00    3.00    --  -42.79 -99.00 -90.00   28
 12  \w   -122.00 -97.00   1.00    3.00    --  -42.79 -99.00  90.00   25
 13  \w     39.00  66.00   1.00    3.00    --   43.29  57.00-120.00   27
 14  \w     19.00 108.00   1.00    3.00    --   43.29  57.00-180.00   89
 15  \w     24.00  95.00   1.00    3.00    --   43.29  57.00  90.00   71
 16  \w     76.00 134.00   1.00   18.00    --  102.90  61.00-120.00   58
 17  \w     30.00  76.00   1.00   18.00    --  102.90 -30.00   0.00   46
 18  \w     93.00 128.00   1.00   18.00    --  102.90 -30.00   0.00   35
 19  \w     78.00 110.00   1.00   18.00    --  102.90  45.00-180.00   32
 20  \w     23.00  56.00   1.00   18.00    --  102.90 -95.00-150.00   33
 21  \w     78.00 104.00   1.00   18.00    --  102.90  77.00 150.00   26
 22  \w     39.00  65.00   1.00   18.00    --  102.90 -95.00  30.00   26
 23  \w     85.00 103.00   1.00   18.00    --  102.90 -95.00  30.00   18
 24  \w     82.00 107.00   1.00   18.00    --  102.90  61.00-150.00   25
 25  \w     80.00 106.00   1.00   18.00    --  102.90  61.00-180.00   26
 26  \w     74.00  99.00   1.00   18.00    --  102.90  77.00-180.00   25
 27  \w     84.00 102.00   1.00   18.00    --  102.90-125.00-180.00   18
 28  \w     55.00 134.00   1.00   18.00    --  102.90 -15.00-120.00   79
 29  \w    133.00 158.00   1.00   18.00    --  102.90  61.00 -30.00   25
;
_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      0.0605435000
_diffrn_orient_matrix_UB_12      -0.0450354000
_diffrn_orient_matrix_UB_13      0.1008403000
_diffrn_orient_matrix_UB_21      0.0726711000
_diffrn_orient_matrix_UB_22      -0.0209346000
_diffrn_orient_matrix_UB_23      -0.1072856000
_diffrn_orient_matrix_UB_31      0.0798868000
_diffrn_orient_matrix_UB_32      0.0531328000
_diffrn_orient_matrix_UB_33      0.0434196000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20335
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.613
_diffrn_reflns_theta_min         3.550
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.735
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_correction_T_min  0.769
_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    1.281
_exptl_crystal_description       plate
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.443
_exptl_crystal_size_mid          0.379
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5205
_refine_ls_number_restraints     85
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1563
_refine_ls_R_factor_gt           0.1024
_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^)+(0.1770P)^2^+1.1966P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3016
_refine_ls_wR_factor_ref         0.3586
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2750
_reflns_number_total             5205
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00169_si_002.cif
_cod_data_source_block           compound_8a
_cod_depositor_comments
'Adding full bibliography for 4032384--4032390.cif.'
_cod_database_code               4032387
_chemical_oxdiff_formula         'C30 H28 N2 O6'
_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. Restrained distances
 C17-C16
 1.54 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C3 \\sim C4 \\sim C5 \\sim C6 \\sim C1 \\sim C2: within 1.7A with sigma of 0.04
and sigma for terminal atoms of 0.08
C29 \\sim C28 \\sim C27 \\sim C26 \\sim C25 \\sim C30: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08
C14 \\sim C13: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.04
C17 \\sim C16: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.04
4.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C14(H14), C18(H18), C20(H20), C21(H21)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C16(H16A,H16B), C22(H22A,H22B)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C26(H26), C27(H27), C28(H28),
 C29(H29), C30(H30)
4.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-06-27
_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 4.369
_oxdiff_exptl_absorpt_empirical_full_min 0.136