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_7046199
_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         'C15 H13 N3'
_chemical_formula_sum            'C15 H13 N3'
_chemical_formula_weight         235.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-03-22 deposited with the CCDC.
2018-05-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2241(4)
_cell_length_b                   19.3350(6)
_cell_length_c                   5.5817(2)
_cell_measurement_reflns_used    1498
_cell_measurement_temperature    173
_cell_measurement_theta_max      70.9630
_cell_measurement_theta_min      4.5400
_cell_volume                     1211.33(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1033
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.981
_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     22.00 106.00   1.00    1.00    --   36.63  38.00 150.00   84
  2  \w     38.00 142.00   1.00    2.87    --  107.00 -15.00 120.00  104
  3  \w     90.00 170.00   1.00    2.87    --  107.00  61.00 -60.00   80
  4  \w     56.00 123.00   1.00    2.87    --  107.00 -61.00-180.00   67
  5  \w     44.00  80.00   1.00    2.87    --  107.00 -95.00-180.00   36
  6  \w     39.00 127.00   1.00    2.87    --  107.00 -30.00 -60.00   88
  7  \w   -101.00 -57.00   1.00    1.00    --  -36.63-178.00 150.00   44
  8  \w   -107.00 -63.00   1.00    1.00    --  -36.63-178.00  60.00   44
  9  \w   -107.00 -57.00   1.00    1.00    --  -36.63-178.00-150.00   50
 10  \w   -109.00 -54.00   1.00    1.00    --  -36.63 178.00 -30.00   55
;
_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      -0.0779412000
_diffrn_orient_matrix_UB_12      -0.0574261000
_diffrn_orient_matrix_UB_13      0.1098558000
_diffrn_orient_matrix_UB_21      0.0828955000
_diffrn_orient_matrix_UB_22      -0.0029209000
_diffrn_orient_matrix_UB_23      0.2196936000
_diffrn_orient_matrix_UB_31      -0.0767507000
_diffrn_orient_matrix_UB_32      0.0551841000
_diffrn_orient_matrix_UB_33      0.1257560000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3555
_diffrn_reflns_point_group_measured_fraction_full 0.900
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.123
_diffrn_reflns_theta_min         4.555
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.619
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (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    1.290
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.097
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2053
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0373
_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^)+(0.0380P)^2^+0.0220P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0892
_reflns_Friedel_coverage         0.608
_reflns_Friedel_fraction_full    0.779
_reflns_Friedel_fraction_max     0.741
_reflns_number_gt                1874
_reflns_number_total             2053
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8dt01256c2.cif
_cod_data_source_block           cu165f
_cod_depositor_comments
'Adding full bibliography for 7046189--7046200.cif.'
_cod_database_code               7046199
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C40H40N3
_chemical_oxdiff_usercomment     'small blue/green block'
_reflns_odcompleteness_completeness 99.01
_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
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C5(H5), C1(H1), C15(H15), C4(H4), C2(H2), C13(H13),
 C12(H12), C14(H14), C3(H3)
;
_shelx_res_checksum              62802
_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 1.089
_oxdiff_exptl_absorpt_empirical_full_min 0.889