Regioselective Zn(OAc)2-catalyzed azide–alkyne cycloaddition in water: the green click-chemistry
Morozova, Maria A.; Yusubov, Mekhman S.; Kratochvil, Bohumil; Eigner, Václav; Bondarev, Alexander A.; Yoshimura, Akira; Saito, Akio; Zhdankin, Viktor V.; Trusova, Marina E.; Postnikov, Pavel S.; Organic Chemistry Frontiers 4 (2017) 978–; doi:10.1039/C6QO00787B

data_1553624
_publ_section_title
;
 Regioselective Zn(OAc)2-catalyzed azide--alkyne cycloaddition in water:
 the green click-chemistry
;
_journal_issue                   6
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              978
_journal_paper_doi               10.1039/C6QO00787B
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C14 H8 Br3 N3'
_chemical_formula_sum            'C14 H8 Br3 N3'
_chemical_formula_weight         457.95
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_update_record
;
2016-10-31 deposited with the CCDC.
2017-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.8945(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.2913(7)
_cell_length_b                   10.0932(4)
_cell_length_c                   19.7897(8)
_cell_measurement_reflns_used    547
_cell_measurement_temperature    180
_cell_measurement_theta_max      22
_cell_measurement_theta_min      2
_cell_volume                     2997.7(2)
_computing_cell_refinement       'Apex3 (Bruker AXS, 2015)'
_computing_data_collection       'Apex3 (Bruker AXS, 2015)'
_computing_data_reduction        'Apex3 (Bruker AXS, 2015)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      180
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex3'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.088
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            41005
_diffrn_reflns_theta_full        26.415
_diffrn_reflns_theta_max         26.415
_diffrn_reflns_theta_min         2.066
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    8.066
_exptl_absorpt_correction_T_max  0.08
_exptl_absorpt_correction_T_min  0.03
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.029
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.581
_exptl_crystal_size_mid          0.375
_exptl_crystal_size_min          0.308
_refine_diff_density_max         1.57
_refine_diff_density_min         -1.48
_refine_ls_extinction_coef       130(6)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9177
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         6136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.0007551
_refine_ls_shift/su_mean         0.0000296
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 3.07 3.51 1.00 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0956
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0956
_reflns_limit_h_max              18
_reflns_limit_h_min              -20
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                4474
_reflns_number_total             6137
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.19
_oxford_diffrn_Wilson_scale      184.84
_oxford_refine_ls_r_factor_ref   0.0659
_oxford_refine_ls_scale          0.070744(18)
_oxford_reflns_number_all        6136
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            c6qo00787b2.cif
_cod_data_source_block           3ia
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'Other' was changed to
'other' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_Hall     '-P 2yn '
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_database_code               1553624