Three-way competition in a topochemical reaction: permutative azide‒alkyne cycloaddition reactions leading to a vast library of products in the crystal
Hema, Kuntrapakam; Sureshan, Kana M.; CrystEngComm 20 (2018) 1478–; doi:10.1039/C8CE00131F

data_7230088
_publ_section_title
;
 Three-way competition in a topochemical reaction: permutative
 azide--alkyne cycloaddition reactions leading to a vast library of
 products in the crystal
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              1478
_journal_paper_doi               10.1039/C8CE00131F
_journal_volume                  20
_journal_year                    2018
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C11 H15 N3 O4'
_chemical_formula_sum            'C11 H15 N3 O4'
_chemical_formula_weight         253.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2018-01-26 deposited with the CCDC.
2018-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2124(6)
_cell_length_b                   10.5820(5)
_cell_length_c                   17.2167(9)
_cell_measurement_reflns_used    2790
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.12
_cell_measurement_theta_min      3.06
_cell_volume                     1314.01(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5999
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_min         2.366
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9804
_exptl_absorpt_correction_T_min  0.9756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_meas      1.279
_exptl_crystal_density_method    NONE
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 802 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2566
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0332
_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^)+(0.0512P)^2^+0.0475P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0928
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2161
_reflns_number_total             2566
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce00131f2.cif
_cod_data_source_block           compound_1
_cod_depositor_comments
'Adding full bibliography for 7230088--7230090.cif.'
_cod_database_code               7230088
_shelx_estimated_absorpt_t_min   0.976
_shelx_estimated_absorpt_t_max   0.981
_shelxl_version_number           2014-3
_shelx_res_checksum              16434