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_7234988
_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(C36 H25 N O)'
_chemical_formula_sum            'C72 H50 N2 O2'
_chemical_formula_weight         975.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                90
_cell_angle_beta                 100.382(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8397(15)
_cell_length_b                   38.561(6)
_cell_length_c                   14.122(2)
_cell_measurement_reflns_used    9750
_cell_measurement_temperature    298
_cell_measurement_theta_max      23.67
_cell_measurement_theta_min      2.338
_cell_volume                     5270.6(14)
_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
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.919
_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  0.0732
_diffrn_reflns_av_unetI/netI     0.0658
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            76731
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.491
_diffrn_reflns_theta_min         1.056
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1439 before and 0.0654 after correction. The Ratio of minimum to maximum transmission is 0.9003. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       plate
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.0057(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     686
_refine_ls_number_reflns         12254
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.1486
_refine_ls_R_factor_gt           0.0728
_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^)+(0.1497P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2040
_refine_ls_wR_factor_ref         0.2574
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5938
_reflns_number_total             12254
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra05350f2.cif
_cod_data_source_block           pj_csc69_0m_a
_cod_original_cell_volume        5270.7(14)
_cod_database_code               7234988
_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
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C38(H38), C39(H39), C40(H40), C41(H41), C46(H46), C47(H47), C48(H48),
 C49(H49), C50(H50), C54(H54), C55(H55), C56(H56), C57(H57), C58(H58), C61(H61),
  C62(H62), C63(H63), C64(H64), C65(H65), C68(H68), C69(H69), C70(H70),
 C71(H71), C72(H72), 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), C32(H32),
 C33(H33), C34(H34), C35(H35), C36(H36)
;
_olex2_submission_special_instructions 'No special instructions were received'