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_4032385
_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         'C26 H27 Br N2 O6'
_chemical_formula_sum            'C26 H27 Br N2 O6'
_chemical_formula_weight         543.40
_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             2016-02-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 114.970(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.9993(7)
_cell_length_b                   10.8867(5)
_cell_length_c                   16.1051(9)
_cell_measurement_reflns_used    6990
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.4300
_cell_measurement_theta_min      3.0480
_cell_volume                     2543.0(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 0.981
_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    -46.00  25.00   1.00    2.50    --  -43.54  57.00 -60.00   71
  2  \w     67.00 106.00   1.00    2.50    --   43.54  77.00   0.00   39
  3  \w     76.00 103.00   1.00   10.00    --  102.90  61.00 -90.00   27
  4  \w    111.00 157.00   1.00   10.00    --  102.90  77.00-120.00   46
  5  \w    133.00 158.00   1.00   10.00    --  102.90  61.00 -90.00   25
  6  \w    110.00 140.00   1.00   10.00    --  102.90  61.00 -60.00   30
  7  \w    109.00 157.00   1.00   10.00    --  102.90  61.00-150.00   48
  8  \w     81.00 130.00   1.00   10.00    --  102.90  45.00 -30.00   49
  9  \w    102.00 155.00   1.00   10.00    --  102.90  61.00  60.00   53
 10  \w     76.00 120.00   1.00   10.00    --  102.90  61.00 -30.00   44
 11  \w     81.00 116.00   1.00   10.00    --  102.90  45.00 -60.00   35
 12  \w     82.00 109.00   1.00   10.00    --  102.90  45.00-120.00   27
 13  \w     77.00 104.00   1.00   10.00    --  102.90  61.00-120.00   27
 14  \w     77.00 103.00   1.00   10.00    --  102.90  57.00-107.03   26
 15  \w     76.00 102.00   1.00   10.00    --  102.90  61.00 -60.00   26
 16  \w     74.00 101.00   1.00   10.00    --  102.90  69.00 -54.59   27
 17  \w     71.00  97.00   1.00   10.00    --  102.90  77.00 -60.00   26
 18  \w     71.00  97.00   1.00   10.00    --  102.90  77.00 -90.00   26
 19  \w     78.00 104.00   1.00   10.00    --  102.90  62.00-126.30   26
 20  \w     77.00 103.00   1.00   10.00    --  102.90  61.00-150.00   26
 21  \w     71.00  97.00   1.00   10.00    --  102.90  77.00-120.00   26
 22  \w     71.00  97.00   1.00   10.00    --  102.90  77.00-150.00   26
 23  \w     19.00 105.00   1.00    2.50    --   43.54  57.00-150.00   86
 24  \w     13.00  98.00   1.00    2.50    --   43.54  77.00 -60.00   85
 25  \w     76.00 158.00   1.00   10.00    --  102.90 126.00  60.00   82
 26  \w     25.00 137.00   1.00   10.00    --  102.90 -15.00  90.00  112
 27  \w    101.00 127.00   1.00   10.00    --  102.90 -77.00 150.00   26
 28  \w     31.00  63.00   1.00   10.00    --  102.90 -77.00 150.00   32
 29  \w     21.00 107.00   1.00   10.00    --  102.90 -95.00   0.00   86
 30  \w     19.00  44.00   1.00    2.50    --   43.54  77.00   0.00   25
 31  \w   -105.00 -79.00   1.00    2.50    --  -43.54 -99.00 150.00   26
 32  \w   -125.00 -89.00   1.00    2.50    --  -43.54 -99.00 -30.00   36
 33  \w   -115.00 -79.00   1.00    2.50    --  -43.54-126.00-120.00   36
;
_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      -0.0747703000
_diffrn_orient_matrix_UB_12      -0.0133846000
_diffrn_orient_matrix_UB_13      -0.0986661000
_diffrn_orient_matrix_UB_21      0.0653182000
_diffrn_orient_matrix_UB_22      0.0585647000
_diffrn_orient_matrix_UB_23      -0.0368036000
_diffrn_orient_matrix_UB_31      0.0377366000
_diffrn_orient_matrix_UB_32      -0.1281300000
_diffrn_orient_matrix_UB_33      -0.0065049000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0875
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22960
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.302
_diffrn_reflns_theta_min         3.047
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.568
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14375
_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    1.419
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.089
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5005
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0598
_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^)+(0.0898P)^2^+0.3820P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1557
_refine_ls_wR_factor_ref         0.1828
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3327
_reflns_number_total             5005
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00169_si_002.cif
_cod_data_source_block           compound_5
_cod_depositor_comments
'Adding full bibliography for 4032384--4032390.cif.'
_cod_database_code               4032385
_chemical_oxdiff_formula         'C26 H27 Br N2 O6'
_chemical_oxdiff_usercomment     'REKHA'S SAMPLE'
_reflns_odcompleteness_completeness 99.96
_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:
 C7(H7), C8(H8), C9(H9), C10(H10), C16(H16), C18(H18), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C17(H17A,H17B,H17C), C22(H22A,H22B,H22C), C26(H26A,H26B,
 H26C)
;
_shelx_res_checksum              14304
_shelx_hkl_checksum              65148
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-02-23
_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 3.404
_oxdiff_exptl_absorpt_empirical_full_min 0.194