Superacid Mediated Intramolecular Condensation: Facile Synthesis of Indenones and Indanones
Gedu, Satyanarayana; Bokka, Venkat Ramulu; RSC Adv.  (2015) –; doi:10.1039/C5RA12234A

data_7221768
_publ_section_title
;
 Superacid Mediated Intramolecular Condensation: Facile Synthesis of
 Indenones and Indanones
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA12234A
_journal_year                    2015
_chemical_formula_moiety         'C14 H16 O3'
_chemical_formula_sum            'C14 H16 O3'
_chemical_formula_weight         232.28
_chemical_melting_point          396.0(10)
_chemical_name_systematic
(E)-5,6-dimethoxy-3-propylidene-2,3-dihydro-1H-inden-1-one
_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'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-22
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-06-23 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.799(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4655(6)
_cell_length_b                   15.5172(9)
_cell_length_c                   8.5918(7)
_cell_measurement_reflns_used    1496
_cell_measurement_temperature    298
_cell_measurement_theta_max      70.9245
_cell_measurement_theta_min      4.8068
_cell_volume                     1225.53(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.9806
_diffrn_measured_fraction_theta_max 0.9806
_diffrn_measurement_details
;
  1 omega   20.00   47.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000 -120.0000 27

  2 omega  -39.00  -13.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000 -120.0000 26

  3 omega  -95.00   -2.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  125.0000   60.0000 93

  4 omega  -51.00  -24.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   50.0000   30.0000 27

  5 omega  -19.00   24.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   50.0000   30.0000 43

  6 omega -109.00  -83.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000 -120.0000 26

  7 omega   33.00  124.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -       54.8681   57.0000  -90.0000 91

  8 omega   68.00  129.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      109.7362  -63.0000 -180.0000 61

  9 omega   64.00   91.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      109.7362  -25.0000  120.0000 27

 10 omega   38.00   93.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      109.7362  -38.0000  -60.0000 55

 11 omega   38.00   91.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      109.7362  -25.0000 -120.0000 53

 12 omega   66.00   93.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      109.7362  -25.0000   30.0000 27

 13 omega   42.00  115.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      109.7362 -111.0000 -180.0000 73

 14 omega   50.00   84.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      109.7362  -38.0000   30.0000 34

 15 omega   45.00   94.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      109.7362  -50.0000    0.0000 49

 16 omega  118.00  148.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      109.7362  178.0000   30.0000 30

 17 omega   48.00  102.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      109.7362  -50.0000  120.0000 54

 18 omega   41.00   89.00   1.0000    3.3900
omega____ theta____ kappa____ phi______ frames
    -      109.7362  -38.0000 -180.0000 48
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0319403000
_diffrn_orient_matrix_UB_12      0.0760356000
_diffrn_orient_matrix_UB_13      -0.1018986000
_diffrn_orient_matrix_UB_21      -0.1088682000
_diffrn_orient_matrix_UB_22      0.0563196000
_diffrn_orient_matrix_UB_23      0.0622728000
_diffrn_orient_matrix_UB_31      0.1231696000
_diffrn_orient_matrix_UB_32      0.0300644000
_diffrn_orient_matrix_UB_33      0.1408846000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4389
_diffrn_reflns_theta_full        71.0624
_diffrn_reflns_theta_max         71.06
_diffrn_reflns_theta_min         4.81
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.712
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2588
_exptl_crystal_description       block
_exptl_crystal_F_000             497.6500
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane and hexane'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.1557
_refine_diff_density_min         -0.2049
_refine_diff_density_rms         0.0436
_refine_ls_d_res_high            0.8150
_refine_ls_d_res_low             9.1923
_refine_ls_goodness_of_fit_ref   1.0820
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    21
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0820
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0545
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0941P)^2^+0.0616P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1498
_refine_ls_wR_factor_ref         0.1759
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              10
_reflns_limit_l_min              0
_reflns_number_gt                1756
_reflns_number_total             2330
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c5ra12234a2.cif
_cod_data_source_block           exp_3546-9-217
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '395-397' was changed to '396.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_cell_volume        1225.52(15)
_cod_database_code               7221768
_chemical_oxdiff_formula         'C13 H12 O3'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C12(H12), C3(H3)
2.c Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c), C14(H14a,H14b,H14c)
;
_olex2_date_sample_data_collection 2014-05-07
_olex2_submission_special_instructions 'No special instructions were received'