Mechanochemical carbon-carbon bond formation that proceeds via a cocrystal intermediate.
Lukin, Stipe; Tireli, Martina; Lončarić, Ivor; Barišić, Dajana; Šket, PrimoŽ; Vrsaljko, Domagoj; di Michiel, Marco; Plavec, Janez; UŽarević, Krunoslav; Halasz, Ivan; Chemical communications (Cambridge, England) 54 (2018) 13216–13219; doi:10.1039/c8cc07853j

data_7122536
_publ_section_title
;
 Mechanochemical carbon-carbon bond formation that proceeds via a
 cocrystal intermediate.
;
_journal_issue                   94
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              13216
_journal_page_last               13219
_journal_paper_doi               10.1039/c8cc07853j
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C12 H10 N2 O5, 0.5(H2 O)'
_chemical_formula_sum            'C12 H11 N2 O5.5'
_chemical_formula_weight         271.2
_chemical_name_common            'Knoevengel prod hemihydrate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-23 deposited with the CCDC.
2018-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 115.972(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.148(4)
_cell_length_b                   14.7902(14)
_cell_length_c                   12.1137(16)
_cell_measurement_reflns_used    770
_cell_measurement_temperature    126.3(6)
_cell_measurement_theta_max      74.6430
_cell_measurement_theta_min      5.0320
_cell_volume                     2278.8(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelX-97(Sheldrick, 1997)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      126.3(6)
_diffrn_detector_area_resol_mean 10.4323
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type
'four-circle diffractometer Xcalibur, Ruby, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source
'micro-focus sealed X-ray tube, Nova (Cu) X-ray Source '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0903
_diffrn_reflns_av_sigmaI/netI    0.1684
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11607
_diffrn_reflns_theta_full        75.85
_diffrn_reflns_theta_max         75.85
_diffrn_reflns_theta_min         2.9878
_exptl_absorpt_coefficient_mu    1.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31634
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow-orange
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1138
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         4672
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.1466
_refine_ls_R_factor_gt           0.0784
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0795P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1808
_refine_ls_wR_factor_ref         0.2288
_reflns_number_gt                2342
_reflns_number_total             4672
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc07853j2.cif
_cod_data_source_block           new_knoaven_2_P21n
_cod_depositor_comments
'Adding full bibliography for 7122535--7122536.cif.'
_cod_original_cell_volume        2278.7(7)
_cod_database_code               7122536
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C12H10N2O5
_chemical_oxdiff_usercomment     'Tiny crystal with poor diffraction''