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_7234987
_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         '0.07(C36 H24 N2 O3)'
_chemical_formula_sum            'C36 H24 N2 O3'
_chemical_formula_weight         39.45
_chemical_melting_point          438.15
_chemical_name_systematic        PJ_B849_55
_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
_audit_creation_date             2018-12-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-03 deposited with the CCDC.	2019-07-16 downloaded from the CCDC.
;
_cell_angle_alpha                70.799(8)
_cell_angle_beta                 84.134(9)
_cell_angle_gamma                71.007(8)
_cell_formula_units_Z            27
_cell_length_a                   10.233(5)
_cell_length_b                   11.256(6)
_cell_length_c                   13.314(7)
_cell_measurement_reflns_used    5212
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      23.66
_cell_measurement_theta_min      2.42
_cell_volume                     1369.4(12)
_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 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0443
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22256
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.420
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1316 before and 0.0579 after correction. The Ratio of minimum to maximum transmission is 0.8370. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear yellowish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       block
_exptl_crystal_F_000             556
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform-Methanol'
_exptl_crystal_size_max          0.81
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       0.010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         4808
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.1190
_refine_ls_R_factor_gt           0.0958
_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^)+(0.1081P)^2^+4.4907P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3124
_refine_ls_wR_factor_ref         0.3260
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3439
_reflns_number_total             4808
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra05350f2.cif
_cod_data_source_block           pj_b849_55_0m_a
_cod_database_code               7234987
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.936
_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), C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25),
  C26(H26), C27(H27), C28(H28), C29(H29), C33(H33), C34(H34), C35(H35), C36(H36)
;
_shelx_res_checksum              66031
_olex2_submission_special_instructions 'No special instructions were received'