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_7234989
_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         'C36 H24 N2 O3'
_chemical_formula_sum            'C36 H24 N2 O3'
_chemical_formula_weight         532.57
_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'
_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                 90.124(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.204(3)
_cell_length_b                   12.6309(13)
_cell_length_c                   18.083(2)
_cell_measurement_reflns_used    8605
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.27
_cell_measurement_theta_min      2.33
_cell_volume                     5528.3(11)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.1316
_diffrn_reflns_av_unetI/netI     0.0806
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            119377
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         0.841
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1337 before and 0.0682 after correction. The Ratio of minimum to maximum transmission is 0.8975. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       needle
_exptl_crystal_F_000             2224
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.0037(4)
_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   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     740
_refine_ls_number_reflns         9638
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1247
_refine_ls_R_factor_gt           0.0536
_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^)+(0.0663P)^2^+0.6518P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1562
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5127
_reflns_number_total             9638
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra05350f2.cif
_cod_data_source_block           a086-176_a
_cod_original_cell_volume        5528.3(10)
_cod_database_code               7234989
_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:
 N3(H3), C38(H38), C39(H39), C40(H40), C41(H41), C46(H46), C47(H47), C48(H48),
 C49(H49), C50(H50), C54(H54), C55(H55), C56(H56), C58(H58), C61(H61), C62(H62),
  C63(H63), C64(H64), C65(H65), C68(H68), C69(H69), C70(H70), C71(H71),
 C72(H72), N1(H1), C2(H2), C3(H3A), 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), C36(H36)
;
_olex2_submission_special_instructions 'No special instructions were received'