Establishment of atropisomerism in 3-indolyl furanoids: a synthetic, experimental and theoretical perspective
Chatterjee, Sourav; Bhattacharjee, Pinaki; Butterfoss, Glenn L.; Achari, Anushree; Jaisankar, Parasuraman; RSC Advances 9 (2019) 22384–; doi:10.1039/C9RA05350F

data_7234986
_publ_section_title
;
 Establishment of atropisomerism in 3-indolyl furanoids: a synthetic,
 experimental and theoretical perspective
;
_journal_issue                   39
_journal_name_full               'RSC Advances'
_journal_page_first              22384
_journal_paper_doi               10.1039/C9RA05350F
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         '2(C38 H29 N O3)'
_chemical_formula_sum            'C76 H58 N2 O6'
_chemical_formula_weight         1095.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-04-01
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2018-06-28 deposited with the CCDC.	2019-07-16 downloaded from the CCDC.
;
_cell_angle_alpha                77.621(4)
_cell_angle_beta                 77.484(3)
_cell_angle_gamma                85.254(4)
_cell_formula_units_Z            2
_cell_length_a                   11.7682(9)
_cell_length_b                   13.1204(11)
_cell_length_c                   19.9515(16)
_cell_measurement_reflns_used    16957
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.25
_cell_volume                     2935.3(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      296.15
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            60770
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.612
_diffrn_reflns_theta_min         1.067
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1494 before and 0.0475 after correction. The Ratio of minimum to maximum transmission is 0.9490. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       plate
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     761
_refine_ls_number_reflns         13116
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0590
_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^)+(0.0612P)^2^+0.8572P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1401
_refine_ls_wR_factor_ref         0.1612
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7885
_reflns_number_total             13116
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra05350f2.cif
_cod_data_source_block           pj_a086_174_0m_a
_cod_database_code               7234986
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C46, C47
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C25(H25),
  C26(H26), C27(H27), C28(H28), C29(H29), C33(H33), C35(H35), C36(H36), N1(H1),
 C3DA(H3DA), C40(H40), C41(H41), C42(H42), C43(H43), C48(H48), C49(H49),
 C50(H50), C51(H51), C52(H52), C56(H56), C57(H57), C58(H58), C59(H59), C60(H60),
  C63(H63), C64(H64), C65(H65), C66(H66), C67(H67), C70(H70), C71(H71)
3.b Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C74(H74A,H74B,H74C), C75(H75A,H75B,
 H75C)
;
_olex2_submission_special_instructions 'No special instructions were received'