Synthesis of 2-Tetrazolylmethyl-isoindolin-1-ones via a One-Pot Ugi-Azide/(N-Acylation/<i>exo</i>-Diels-Alder)/Dehydration Process.
Rentería-Gómez, Angel; Islas-Jácome, Alejandro; Cruz-Jiménez, Alicia E; Manzano-Velázquez, Jessica C; Rojas-Lima, Susana; Jiménez-Halla, J Oscar C; Gámez-Montaño, Rocío; ACS omega 1 (2016) 943–951; doi:10.1021/acsomega.6b00281

data_4516828
_publ_section_title
;
 Synthesis of 2-Tetrazolylmethyl-isoindolin-1-ones via a One-Pot
 Ugi-Azide/(N-Acylation/<i>exo</i>-Diels-Alder)/Dehydration Process.
;
_journal_issue                   5
_journal_name_full               'ACS omega'
_journal_page_first              943
_journal_page_last               951
_journal_paper_doi               10.1021/acsomega.6b00281
_journal_volume                  1
_journal_year                    2016
_chemical_formula_moiety         'C21 H27 N5 O3'
_chemical_formula_sum            'C21 H27 N5 O3'
_chemical_formula_weight         397.47
_chemical_melting_point          486
_chemical_name_systematic
'2-(1-(1-cyclohexyl-1H-tetrazol-5-yl)-2,2-dimethylpropyl)-3-oxoisoindoline-4-carboxylic acid'
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2016-09-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                102.960(4)
_cell_angle_beta                 104.714(4)
_cell_angle_gamma                107.837(4)
_cell_formula_units_Z            2
_cell_length_a                   9.2469(4)
_cell_length_b                   10.8452(4)
_cell_length_c                   11.8162(5)
_cell_measurement_reflns_used    7204
_cell_measurement_temperature    291
_cell_measurement_theta_max      77.2740
_cell_measurement_theta_min      4.0360
_cell_volume                     1030.64(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      291
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3659
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_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   -117.00 -18.00   1.00    1.11    --  -42.36 -38.00  30.00   99
  2  \w    -71.00  31.00   1.00    1.11    --  -42.36  57.00 -60.00  102
  3  \w    -50.00  32.00   1.00    1.11    --  -42.36  38.00-180.00   82
  4  \w    -50.00  32.00   1.00    1.11    --  -42.36  38.00-150.00   82
  5  \w     53.00 130.00   1.00    1.11    --   42.36-178.00  60.00   77
  6  \w     57.00 131.00   1.00    1.11    --   42.36 178.00-150.00   74
  7  \w     41.00  98.00   1.00    4.43    --  114.00 -45.00 -30.00   57
  8  \w     41.00 121.00   1.00    4.43    --  114.00-125.00 -90.00   80
  9  \w     41.00  98.00   1.00    4.43    --  114.00 -45.00 120.00   57
 10  \w     42.00 143.00   1.00    4.43    --  114.00 -61.00 -30.00  101
 11  \w     31.00 109.00   1.00    4.43    --  114.00 -94.00-180.00   78
 12  \w     86.00 178.00   1.00    4.43    --  114.00  30.00 -30.00   92
 13  \w     41.00  98.00   1.00    4.43    --  114.00 -45.00  60.00   57
 14  \w     31.00 109.00   1.00    4.43    --  114.00 -94.00 -60.00   78
 15  \w     31.00 109.00   1.00    4.43    --  114.00 -94.00  90.00   78
 16  \w     31.00 109.00   1.00    4.43    --  114.00 -94.00 150.00   78
 17  \w     61.00 178.00   1.00    4.43    --  114.00  15.00-150.00  117
 18  \w     38.00  91.00   1.00    4.43    --  114.00 -30.00-180.00   53
 19  \w     86.00 178.00   1.00    4.43    --  114.00  30.00  30.00   92
 20  \w     42.00 143.00   1.00    4.43    --  114.00 -61.00-150.00  101
 21  \w     41.00 121.00   1.00    4.43    --  114.00-125.00 -30.00   80
 22  \w     41.00 121.00   1.00    4.43    --  114.00-125.00  60.00   80
 23  \w     38.00  91.00   1.00    4.43    --  114.00 -30.00-150.00   53
 24  \w     86.00 178.00   1.00    4.43    --  114.00  30.00  90.00   92
 25  \w   -119.00 -10.00   1.00    1.11    --  -42.36 -77.00 -90.00  109
 26  \w   -119.00 -10.00   1.00    1.11    --  -42.36 -77.00 150.00  109
 27  \w   -115.00 -14.00   1.00    1.11    --  -42.36 -57.00-150.00  101
 28  \w   -115.00 -14.00   1.00    1.11    --  -42.36 -57.00 -60.00  101
 29  \w   -119.00 -10.00   1.00    1.11    --  -42.36 -77.00-180.00  109
 30  \w   -119.00 -10.00   1.00    1.11    --  -42.36 -77.00  60.00  109
 31  \w   -116.00 -55.00   1.00    1.11    --  -42.36-152.00 -82.00   61
 32  \w     85.00 178.00   1.00    4.43    --  114.00  61.00-180.00   93
 33  \w     85.00 178.00   1.00    4.43    --  114.00  61.00  30.00   93
 34  \w     85.00 178.00   1.00    4.43    --  114.00  61.00 -30.00   93
 35  \w     85.00 178.00   1.00    4.43    --  114.00  61.00 -90.00   93
 36  \w     85.00 178.00   1.00    4.43    --  114.00  61.00-150.00   93
 37  \w     88.00 178.00   1.00    4.43    --  114.00  45.00 120.00   90
 38  \w     85.00 178.00   1.00    4.43    --  114.00  61.00  90.00   93
 39  \w     86.00 178.00   1.00    4.43    --  114.00  30.00 -90.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1260754000
_diffrn_orient_matrix_UB_12      -0.0491417000
_diffrn_orient_matrix_UB_13      0.0671635000
_diffrn_orient_matrix_UB_21      0.0105872000
_diffrn_orient_matrix_UB_22      -0.0691205000
_diffrn_orient_matrix_UB_23      -0.1249493000
_diffrn_orient_matrix_UB_31      0.1372566000
_diffrn_orient_matrix_UB_32      0.1332689000
_diffrn_orient_matrix_UB_33      0.0154506000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21428
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.512
_diffrn_reflns_theta_min         4.095
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_recrystallization_method
'Crystal were obteined from Hexanos / CH2Cl2 / CDCl3 (80/10/10; v/v/v)'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4353
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0706P)^2^+0.1257P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1231
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3586
_reflns_number_total             4353
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao6b00281_si_003.cif
_cod_data_source_block           srl268_jcmv50
_cod_original_cell_volume        1030.65(8)
_cod_database_code               4516828
_chemical_oxdiff_formula         'C19 H26 N5 O1'
_chemical_oxdiff_usercomment     ' '
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
2.e Idealised tetrahedral OH refined as rotating group:
 O25(H25)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-05-25
_olex2_exptl_crystal_mounting_method
'Crystal were mounted on a glass fiber using paraton N'
_olex2_submission_original_sample_id 1m
_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 1.689
_oxdiff_exptl_absorpt_empirical_full_min 0.884