Thermally Induced [3 + 2] Cycloaddition of Alkynyl-Tethered Diazoamides: Synthetic and Mechanistic Insights.
Zhang, Cheng; Huang, Jingjing; Qiu, Lihua; Xu, Xinfang; Organic letters 18 (2016) 6208–6211; doi:10.1021/acs.orglett.6b03288

data_1555969
_publ_section_title
;
 Thermally Induced [3 + 2] Cycloaddition of Alkynyl-Tethered Diazoamides:
 Synthetic and Mechanistic Insights.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6208
_journal_page_last               6211
_journal_paper_doi               10.1021/acs.orglett.6b03288
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C12 H17 N3 O, 2(H2 O)'
_chemical_formula_sum            'C12 H21 N3 O3'
_chemical_formula_weight         255.32
_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   mixed
_atom_sites_solution_primary     direct
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Olex2 1.2-alpha
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_cell_length_c                   17.5830(16)
_cell_measurement_reflns_used    1430
_cell_measurement_temperature    278.04(10)
_cell_measurement_theta_max      26.0430
_cell_measurement_theta_min      3.3770
_cell_volume                     1346.62(19)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      278.04(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -59.00   36.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6514  -57.0000    0.0000 95

  2 omega  -14.00   77.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6514   57.0000  150.0000 91

  3 omega   47.00   73.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6514  165.0000    2.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
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_diffrn_orient_matrix_UB_11      -0.0213839000
_diffrn_orient_matrix_UB_12      -0.0123704000
_diffrn_orient_matrix_UB_13      -0.0400253000
_diffrn_orient_matrix_UB_21      -0.0530089000
_diffrn_orient_matrix_UB_22      0.0313633000
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_diffrn_orient_matrix_UB_31      0.0131474000
_diffrn_orient_matrix_UB_32      0.1068027000
_diffrn_orient_matrix_UB_33      -0.0065087000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0707
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_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6322
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.137
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95324
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_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       plate
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_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.044
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_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2739
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0529
_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^)+(0.0397P)^2^+0.0221P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_Friedel_coverage         0.000
_reflns_number_gt                1714
_reflns_number_total             2739
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03288_si_003.cif
_cod_data_source_block           g160919a-1
_cod_original_cell_volume        1346.63(19)
_cod_database_code               1555969
_chemical_oxdiff_formula         'C H O N'
_reflns_odcompleteness_completeness 99.79
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_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,
 H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'