Synthesis of α-indolylacrylates as potential anticancer agents using a Brønsted acid ionic liquid catalyst and the butyl acetate solvent
El-Harairy, Ahmed; Shaheen, Mennatallah; Li, Jun; Wu, Yuzhou; Li, Minghao; Gu, Yanlong; RSC Advances 10 (2020) 13507–13516; doi:10.1039/D0RA00990C

data_7240246
_publ_section_title
;
 Synthesis of \a-indolylacrylates as potential anticancer agents using a
 Br\/onsted acid ionic liquid catalyst and the butyl acetate solvent
;
_journal_issue                   23
_journal_name_full               'RSC Advances'
_journal_page_first              13507
_journal_page_last               13516
_journal_paper_doi               10.1039/D0RA00990C
_journal_volume                  10
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C28 H30 N2 O4'
_chemical_formula_sum            'C28 H30 N2 O4'
_chemical_formula_weight         458.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-29 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.819(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.179(2)
_cell_length_b                   8.8178(15)
_cell_length_c                   17.233(2)
_cell_measurement_reflns_used    4180
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      27.8020
_cell_measurement_theta_min      2.3360
_cell_volume                     2387.4(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -15.00  14.00   1.00    7.50    --  -11.74 -99.00 -30.00   29
  2  \w    -76.00  15.00   1.00    7.50    --  -11.74 -57.00  30.00   91
  3  \w    -35.00  61.00   1.00    7.50    --  -11.74  57.00-180.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0448659000
_diffrn_orient_matrix_UB_12      -0.0024627000
_diffrn_orient_matrix_UB_13      -0.0144229000
_diffrn_orient_matrix_UB_21      0.0013942000
_diffrn_orient_matrix_UB_22      -0.0803780000
_diffrn_orient_matrix_UB_23      0.0010856000
_diffrn_orient_matrix_UB_31      -0.0048222000
_diffrn_orient_matrix_UB_32      0.0014016000
_diffrn_orient_matrix_UB_33      0.0398478000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0860
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11382
_diffrn_reflns_point_group_measured_fraction_full 0.862
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        24.990
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_min         2.434
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.043
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            bronze
_exptl_crystal_density_diffrn    0.638
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 1817 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         7256
_refine_ls_number_restraints     109
_refine_ls_restrained_S_all      1.309
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0732
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0829P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1990
_refine_ls_wR_factor_ref         0.2059
_reflns_Friedel_coverage         0.610
_reflns_Friedel_fraction_full    0.704
_reflns_Friedel_fraction_max     0.704
_reflns_number_gt                6367
_reflns_number_total             7256
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra00990c2.cif
_cod_data_source_block           exp_1776
_cod_depositor_comments          'Adding full bibliography for 7240246.cif.'
_cod_original_cell_volume        2387.3(6)
_cod_database_code               7240246
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.994
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C1, C2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C23, C24
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O2, C12
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C16, C7
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N1, C7, C11
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C1, C8, C9, C10
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C2, C3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2: within 2A with sigma of 0.002 and sigma for terminal atoms of 0.004
C23 \\sim C24: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
O2 \\sim C12: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
C16 \\sim C17: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
N1 \\sim C7 \\sim C11: within 2A with sigma of 0.002 and sigma for terminal
atoms of 0.004
C1 \\sim C8 \\sim C9 \\sim C10: within 2A with sigma of 0.002 and sigma for
terminal atoms of 0.004
C2 \\sim C3: within 2A with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C6) \\sim Ueq, Uanis(C0AA) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.004
Uanis(C7) \\sim Ueq, Uanis(C23) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.004
Uanis(C8) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C28) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C10) = Uanis(C11) = Uanis(C12) = Uanis(C13) = Uanis(C14)
Uanis(O1) = Uanis(C12)
Uanis(N1) = Uanis(C6)
Uanis(N2) = Uanis(C16)
Uanis(C1) = Uanis(C6)
Uanis(C3) = Uanis(C4)
Uanis(C9) = Uanis(C25)
Uanis(C17) = Uanis(C18) = Uanis(C19) = Uanis(C20)
Uanis(N2) = Uanis(C22)
Uanis(O2) = Uanis(C23)
Uanis(C4) = Uanis(C5)
Uanis(C7) = Uanis(C11)
Uanis(C9) = Uanis(C10)
Uanis(O2) = Uanis(C12)
Uanis(O4) = Uanis(C25)
Uanis(C5) = Uanis(C6)
Uanis(C13) = Uanis(C17)
Uanis(C26) = Uanis(C27)
4.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C26(H26A,H26B), C23(H23A,H23B)
4.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C14(H14), C20(H20), C5(H5), C19(H19), C2(H2), C21(H21), C3(H3),
 C4(H4)
4.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C22(H22A,H22B,H22C), C0AA(H0AA,H0AB,H0AC), C27(H27A,H27B,
 H27C), C24(H24A,H24B,H24C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.920
_oxdiff_exptl_absorpt_empirical_full_min 0.625