Apical Functionalization of Chiral Heterohelicenes
Sravan K. Surampudi; G. Nagarjuna; Daiki Okamoto; Piyali D. Chaudhuri; D. Venkataraman; Journal of Organic Chemistry 77 (2012) 2074–2079; doi:10.1021/jo202623u

data_4026996
_publ_contact_author_address
;
Department of Chemistry
University of Massachusetts Amherst
710 N. Pleasant Street
Amherst, MA 01003
;
_publ_contact_author_email       dv@chem.umass.edu
_publ_contact_author_fax         413-545-4490
_publ_contact_author_name        'Dhandapani Venkataraman'
_publ_contact_author_phone       413-545-2028
_publ_section_title
;
 Apical Functionalization of Chiral Heterohelicenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2074
_journal_page_last               2079
_journal_paper_doi               10.1021/jo202623u
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C35 H34 Br1 N1 O6'
_chemical_formula_sum            'C31.25 H25 Br N O6'
_chemical_formula_weight         590.43
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2011-12-17T10:18:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 91.0210(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.35380(10)
_cell_length_b                   29.5716(5)
_cell_length_c                   23.3724(4)
_cell_measurement_reflns_used    10196
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      4.076
_cell_measurement_wavelength     0.71073
_cell_volume                     5772.89(16)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.995116E-1
_diffrn_orient_matrix_UB_12      0.187397E-1
_diffrn_orient_matrix_UB_13      0.13087E-2
_diffrn_orient_matrix_UB_21      -0.599671E-1
_diffrn_orient_matrix_UB_22      -0.240357E-1
_diffrn_orient_matrix_UB_23      -0.215134E-1
_diffrn_orient_matrix_UB_31      -0.289043E-1
_diffrn_orient_matrix_UB_32      -0.146508E-1
_diffrn_orient_matrix_UB_33      0.369681E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.057
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20026
_diffrn_reflns_reduction_process
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         4.09
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    1.467
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       needle
_exptl_crystal_F_000             2420
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.779
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.049(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1401
_refine_ls_number_reflns         20026
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.1092
_refine_ls_R_factor_gt           0.0745
_refine_ls_shift/su_max          0.081
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0980P)^2^+4.4689P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1753
_refine_ls_wR_factor_ref         0.1917
_reflns_number_gt                14563
_reflns_number_total             20026
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202623u_si_003_4.cif
_cod_data_source_block           compoundM1
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4026996