Copper(ii)-benzotriazole coordination compounds in click chemistry: a diagnostic reactivity study.
Loukopoulos, Edward; Abdul-Sada, Alaa; Csire, Gizella; Kállay, Csilla; Brookfield, Adam; Tizzard, Graham J.; Coles, Simon J.; Lykakis, Ioannis N.; Kostakis, George E.; Dalton transactions (Cambridge, England : 2003) 47 (2018) 10491–10508; doi:10.1039/c8dt01256c

data_7046196
_publ_section_title
;
 Copper(ii)-benzotriazole coordination compounds in click chemistry: a
 diagnostic reactivity study.
;
_journal_issue                   31
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              10491
_journal_page_last               10508
_journal_paper_doi               10.1039/c8dt01256c
_journal_volume                  47
_journal_year                    2018
_chemical_formula_moiety         '2(H2 O), C14 H14 N4'
_chemical_formula_sum            'C14 H18 N4 O2'
_chemical_formula_weight         274.32
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-01-09
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_audit_update_record
;
2018-03-22 deposited with the CCDC.
2018-05-01 downloaded from the CCDC.
;
_cell_angle_alpha                80.648(10)
_cell_angle_beta                 69.951(9)
_cell_angle_gamma                84.374(10)
_cell_formula_units_Z            2
_cell_length_a                   8.1128(8)
_cell_length_b                   8.7716(11)
_cell_length_c                   10.9028(11)
_cell_measurement_reflns_used    1142
_cell_measurement_temperature    173
_cell_measurement_theta_max      70.5740
_cell_measurement_theta_min      5.1170
_cell_volume                     718.41(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.44a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.44a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.44a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1033
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     23.00 101.00   1.00    1.00    --   36.75  57.00 -30.00   78
  2  \w     41.00 124.00   1.00    2.67    --  107.00 -45.00 -90.00   83
  3  \w     72.00 130.00   1.00    2.67    --  107.00 -93.00 -30.02   58
  4  \w     63.00 105.00   1.00    2.67    --  107.00 -91.00-111.65   42
  5  \w     57.00 120.00   1.00    2.67    --  107.00 -45.00-180.00   63
  6  \w    102.00 172.00   1.00    2.67    --  107.00  61.00-180.00   70
  7  \w     36.00  89.00   1.00    1.00    --   36.75 178.00 -30.00   53
  8  \w     25.00  99.00   1.00    1.00    --   36.75  57.00 120.00   74
  9  \w     39.00 123.00   1.00    2.67    --  107.00 -45.00  30.00   84
 10  \w     50.00 121.00   1.00    2.67    --  107.00 -92.00 121.31   71
 11  \w     44.00 112.00   1.00    2.67    --  107.00 -45.00 120.00   68
 12  \w     41.00 174.00   1.00    2.67    --  107.00   0.00 150.00  133
 13  \w     21.00 101.00   1.00    1.00    --   36.75  57.00  60.00   80
 14  \w    -25.00  76.00   1.00    1.00    --   36.75 -99.00-150.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1144370000
_diffrn_orient_matrix_UB_12      0.1035579000
_diffrn_orient_matrix_UB_13      -0.1215230000
_diffrn_orient_matrix_UB_21      0.0347830000
_diffrn_orient_matrix_UB_22      -0.1345625000
_diffrn_orient_matrix_UB_23      -0.0818406000
_diffrn_orient_matrix_UB_31      -0.1632219000
_diffrn_orient_matrix_UB_32      0.0540161000
_diffrn_orient_matrix_UB_33      -0.0399647000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0721
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3676
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.949
_diffrn_reflns_theta_min         4.358
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.716
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91060
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.44a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0484
_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^)+(0.0460P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1284
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1828
_reflns_number_total             2629
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8dt01256c2.cif
_cod_data_source_block           o-il
_cod_depositor_comments
'Adding full bibliography for 7046189--7046200.cif.'
_cod_original_cell_volume        718.41(15)
_cod_database_code               7046196
_chemical_oxdiff_formula         C20H20N6O2
_reflns_odcompleteness_completeness 97.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O2(H2A,H2B), O1(H1A,H1B)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C6(H6), C7(H7), C1(H1), C14(H14), C12(H12), C8(H8), C13(H13), C2(H2),
 C3(H3)
;
_shelx_res_checksum              18228
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2017-01-09
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.800
_oxdiff_exptl_absorpt_empirical_full_min 0.865