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_4032390
_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         'C35 H35 N3 O6'
_chemical_formula_sum            'C35 H35 N3 O6'
_chemical_formula_weight         593.66
_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             2016-09-14
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                97.385(2)
_cell_angle_beta                 97.614(2)
_cell_angle_gamma                113.028(3)
_cell_formula_units_Z            2
_cell_length_a                   10.7283(3)
_cell_length_b                   11.4578(4)
_cell_length_c                   14.3942(3)
_cell_measurement_reflns_used    17712
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.8390
_cell_measurement_theta_min      4.3060
_cell_volume                     1582.16(9)
_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
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%$getVar(olex2_reference_short)%
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_computing_structure_refinement
;
%$getVar(refinement_reference_short)%
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_computing_structure_solution
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%$getVar(solution_reference_short)%
;
_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 0.988
_diffrn_measured_fraction_theta_max 0.970
_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     19.00  56.00   1.00    1.00    --   43.29  38.00 -60.00   37
  2  \w     61.00 115.00   1.00    1.00    --   43.29  38.00 -60.00   54
  3  \w    110.00 143.00   1.00    1.00    --   78.00  76.00 -90.18   33
  4  \w    113.00 158.00   1.00    1.00    --  102.90  77.00-120.00   45
  5  \w    111.00 149.00   1.00    1.00    --  102.90  77.00   0.00   38
  6  \w    117.00 143.00   1.00    1.00    --   74.00  75.00  56.24   26
  7  \w    120.00 149.00   1.00    1.00    --  102.90  77.00  60.00   29
  8  \w     71.00 157.00   1.00    1.00    --  102.00  75.00  90.81   86
  9  \w     72.00 117.00   1.00    1.00    --  102.90  77.00  60.00   45
 10  \w     71.00 108.00   1.00    1.00    --  102.90  77.00   0.00   37
 11  \w     68.00 148.00   1.00    1.00    --   98.00  72.00  36.53   80
 12  \w     72.00 153.00   1.00    1.00    --  102.90  77.00 -30.00   81
 13  \w    100.00 158.00   1.00    1.00    --  102.90  77.00-150.00   58
 14  \w     95.00 121.00   1.00    1.00    --   90.00  75.00-171.66   26
 15  \w     74.00 109.00   1.00    1.00    --  102.90  77.00-120.00   35
 16  \w     71.00 140.00   1.00    1.00    --  102.90  77.00 -60.00   69
 17  \w     71.00 157.00   1.00    1.00    --  102.90  77.00 -90.00   86
 18  \w     71.00  97.00   1.00    1.00    --  102.90  77.00-150.00   26
 19  \w     63.00  92.00   1.00    1.00    --   90.00  75.00-171.66   29
 20  \w     46.00  72.00   1.00    1.00    --   78.00  77.00-165.71   26
 21  \w     38.00  67.00   1.00    1.00    --   66.00  75.00-132.90   29
 22  \w     48.00  73.00   1.00    1.00    --   78.00  76.00 -90.18   25
 23  \w     48.00  73.00   1.00    1.00    --   78.00  73.00 -31.20   25
 24  \w     57.00  89.00   1.00    1.00    --   82.00  63.00  -1.73   32
 25  \w     43.00  76.00   1.00    1.00    --   74.00  75.00  56.24   33
 26  \w     73.00 133.00   1.00    1.00    --  102.90  77.00 120.00   60
 27  \w     71.00 152.00   1.00    1.00    --  102.90  77.00 150.00   81
 28  \w     59.00 113.00   1.00    1.00    --   43.29  57.00 150.00   54
 29  \w     49.00  75.00   1.00    1.00    --   78.00  70.00 159.31   26
 30  \w     43.00  78.00   1.00    1.00    --   74.00  74.00 129.79   35
 31  \w     30.00  56.00   1.00    1.00    --   62.00  77.00  32.05   26
 32  \w     36.00  78.00   1.00    1.00    --   66.00  77.00  -9.13   42
 33  \w     35.00  61.00   1.00    1.00    --   66.00  76.00 -48.38   26
 34  \w     22.00  47.00   1.00    1.00    --   54.00  78.00 -30.53   25
 35  \w     14.00  39.00   1.00    1.00    --   46.00  80.00 -44.11   25
 36  \w     26.00  56.00   1.00    1.00    --   58.00  77.00-104.73   30
 37  \w     32.00  58.00   1.00    1.00    --   62.00  72.00-147.82   26
 38  \w     12.00  37.00   1.00    1.00    --   46.00  84.00-161.96   25
 39  \w     37.00 124.00   1.00    1.00    --  102.90 -30.00 -90.00   87
 40  \w     79.00 130.00   1.00    1.00    --  102.90 -77.00 -90.00   51
 41  \w     39.00 114.00   1.00    1.00    --  102.90-105.00 -47.00   75
 42  \w     36.00 117.00   1.00    1.00    --  102.90 -61.00  30.00   81
 43  \w     89.00 118.00   1.00    1.00    --  102.90-126.00 150.00   29
 44  \w     42.00 121.00   1.00    1.00    --  102.90 -45.00 150.00   79
 45  \w     30.00  61.00   1.00    1.00    --   62.00  77.00 124.10   31
 46  \w     22.00  47.00   1.00    1.00    --   54.00  78.00 104.09   25
 47  \w     19.00  54.00   1.00    1.00    --   43.29  57.00 150.00   35
 48  \w      8.00  33.00   1.00    1.00    --   42.00  87.00 145.13   25
 49  \w      9.00  36.00   1.00    1.00    --   42.00  84.00  59.09   27
 50  \w     19.00 112.00   1.00    1.00    --   43.29  38.00  60.00   93
 51  \w     15.00  97.00   1.00    1.00    --   43.29-126.00 -90.00   82
 52  \w     22.00 110.00   1.00    1.00    --  102.90 -95.00-180.00   88
 53  \w    -26.00  68.00   1.00    1.00    --   43.29 -57.00   0.00   94
 54  \w     79.00 105.00   1.00    1.00    --  102.90 -95.00  30.00   26
;
_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      0.0116170000
_diffrn_orient_matrix_UB_12      0.0525616000
_diffrn_orient_matrix_UB_13      0.1063008000
_diffrn_orient_matrix_UB_21      0.1458920000
_diffrn_orient_matrix_UB_22      0.1035781000
_diffrn_orient_matrix_UB_23      0.0032649000
_diffrn_orient_matrix_UB_31      -0.0627993000
_diffrn_orient_matrix_UB_32      0.0933887000
_diffrn_orient_matrix_UB_33      -0.0286923000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25380
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.344
_diffrn_reflns_theta_min         3.160
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62090
_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    1.246
_exptl_crystal_description       irregular
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         6172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0546
_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^)+(0.0754P)^2^+0.4900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1532
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5266
_reflns_number_total             6172
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00169_si_002.cif
_cod_data_source_block           compound_19b
_cod_depositor_comments
'Adding full bibliography for 4032384--4032390.cif.'
_cod_original_cell_volume        1582.16(8)
_cod_database_code               4032390
_publ_section_exptl
;
Any special experimental details
;
_chemical_oxdiff_formula         'C35 H35 N3 O6'
_reflns_odcompleteness_completeness 98.96
_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:
 C9(H9), C10(H10), C14(H14), C15(H15), C22(H22), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C19(H19A,H19B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C30(H30), C31(H31), C33(H33), C34(H34)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C20(H20A,H20B,H20C), C25(H25A,H25B,H25C), C28(H28A,H28B,
 H28C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-09-12
_olex2_submission_original_sample_id RS110816A_upper
_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 4.897
_oxdiff_exptl_absorpt_empirical_full_min 0.589