Thermal azide–alkene cycloaddition reactions: straightforward multi-gram access to Δ2-1,2,3-triazolines in deep eutectic solvents
Sebest, Filip; Casarrubios, Luis; Rzepa, Henry S.; White, Andrew J. P.; Díez-González, Silvia; Green Chemistry 20 (2018) 4023–; doi:10.1039/C8GC01797B

data_7231312
_publ_section_title
;
 Thermal azide--alkene cycloaddition reactions: straightforward multi-gram
 access to \D2-1,2,3-triazolines in deep eutectic solvents
;
_journal_issue                   17
_journal_name_full               'Green Chemistry'
_journal_page_first              4023
_journal_paper_doi               10.1039/C8GC01797B
_journal_volume                  20
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H23 N3 O4'
_chemical_formula_sum            'C18 H23 N3 O4'
_chemical_formula_weight         345.39
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2018-05-14 deposited with the CCDC.
2018-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.720(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.35503(14)
_cell_length_b                   10.1690(2)
_cell_length_c                   32.7300(7)
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_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      73.6350
_cell_measurement_theta_min      4.5380
_cell_volume                     1780.31(7)
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_collection       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2017)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.4115
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Agilent Xcalibur PX Ultra A'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            5662
_diffrn_reflns_point_group_measured_fraction_full 0.666
_diffrn_reflns_point_group_measured_fraction_max 0.631
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.743
_diffrn_reflns_theta_min         4.057
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.757
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.853
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       plates
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.305
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
; 
 Flack x determined using 718 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     492
_refine_ls_number_reflns         4567
_refine_ls_number_restraints     154
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0672P)^2^+0.1713P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1355
_reflns_Friedel_coverage         0.263
_reflns_Friedel_fraction_full    0.309
_reflns_Friedel_fraction_max     0.279
_reflns_number_gt                3891
_reflns_number_total             4567
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8gc01797b2.cif
_cod_data_source_block           5du_prime
_cod_depositor_comments
'Adding full bibliography for 7231311--7231316.cif.'
_cod_original_cell_volume        1780.32(7)
_cod_database_code               7231312
_shelx_shelxl_version_number     2017/1
_shelx_res_checksum              47442