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_7046195
_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         'C10 H11 N3 O'
_chemical_formula_sum            'C10 H11 N3 O'
_chemical_formula_weight         189.22
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-11-08
_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                93.064(8)
_cell_angle_beta                 106.687(11)
_cell_angle_gamma                104.934(10)
_cell_formula_units_Z            4
_cell_length_a                   8.2035(12)
_cell_length_b                   11.0403(11)
_cell_length_c                   11.2020(11)
_cell_measurement_reflns_used    1595
_cell_measurement_temperature    173
_cell_measurement_theta_max      71.1270
_cell_measurement_theta_min      4.1800
_cell_volume                     930.1(2)
_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    'SIR2004 (Burla et al., 2007)'
_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 0.983
_diffrn_measured_fraction_theta_max 0.958
_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     10.00 104.00   1.00    4.89    --   36.75  77.00 120.00   94
  2  \w    -30.00  63.00   1.00    4.89    --   36.75 -77.00 -90.00   93
  3  \w     10.00 101.00   1.00    4.89    --   36.75  77.00  30.00   91
  4  \w    -23.00  75.00   1.00    4.89    --   36.75 -99.00-150.00   98
  5  \w     41.00 121.00   1.00   24.00    --  107.00 -45.00   0.00   80
  6  \w     69.00 142.00   1.00   24.00    --  107.00 -92.00-109.27   73
  7  \w     40.00 124.00   1.00   24.00    --  107.00 -45.00-180.00   84
  8  \w     85.00 123.00   1.00   24.00    --  107.00 -45.00 -90.00   38
  9  \w     42.00 123.00   1.00   24.00    --  107.00 -45.00  90.00   81
 10  \w     41.00  82.00   1.00   24.00    --  107.00 -45.00 -90.00   41
 11  \w    110.00 166.00   1.00   24.00    --  107.00  45.00 150.00   56
 12  \w     43.00 169.00   1.00   24.00    --  107.00   0.00 120.00  126
 13  \w     46.00 115.00   1.00   24.00    --  107.00 -92.00 153.56   69
 14  \w     77.00 142.00   1.00   24.00    --  107.00 -93.00 -18.64   65
;
_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      -0.1146424000
_diffrn_orient_matrix_UB_12      0.0121848000
_diffrn_orient_matrix_UB_13      0.0849400000
_diffrn_orient_matrix_UB_21      0.1350748000
_diffrn_orient_matrix_UB_22      0.1269214000
_diffrn_orient_matrix_UB_23      0.0681026000
_diffrn_orient_matrix_UB_31      -0.1022625000
_diffrn_orient_matrix_UB_32      0.0707256000
_diffrn_orient_matrix_UB_33      -0.0956994000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5011
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.194
_diffrn_reflns_theta_min         4.160
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.744
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94611
_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    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0417P)^2^+0.0128P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1216
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2383
_reflns_number_total             3462
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8dt01256c2.cif
_cod_data_source_block           cu229
_cod_depositor_comments
'Adding full bibliography for 7046189--7046200.cif.'
_cod_database_code               7046195
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C50H50N6O2
_reflns_odcompleteness_completeness 98.15
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1(0.052) H2A(0.05) H18(0.032) H8(0.034) H17A(0.037) H17B(0.037)
 H20A(0.038) H20B(0.038) H4(0.041) H10A(0.039) H10B(0.039) H7A(0.039)
 H7B(0.039) H6(0.044) H13(0.045) H2(0.049) H15(0.05) H1A(0.052) H12(0.054)
 H3(0.047) H11(0.054) H16(0.059)
 Fixed X: H1(0.3276) H2A(0.1736) H18(-0.3086) H8(0.8117) H17A(-0.3635) H17B(-
 0.1897) H20A(0.0541) H20B(-0.1317) H4(0.9593) H10A(0.6352) H10B(0.4484)
 H7A(0.6903) H7B(0.8658) H6(0.5577) H13(-0.2609) H2(0.7841) H15(-0.2416)
 H1A(0.574) H12(-0.2814) H3(0.9761) H11(-0.2751) H16(-0.2553)
 Fixed Y: H1(0.3931) H2A(0.613) H18(0.3656) H8(0.6435) H17A(0.2826)
 H17B(0.3218) H20A(0.4233) H20B(0.4553) H4(0.9303) H10A(0.5522) H10B(0.5829)
 H7A(0.687) H7B(0.7212) H6(0.8514) H13(0.1353) H2(1.213) H15(0.0982)
 H1A(1.0656) H12(-0.0788) H3(1.1446) H11(-0.2038) H16(-0.1149)
 Fixed Z: H1(0.332) H2A(0.1628) H18(0.2505) H8(0.2495) H17A(0.4567)
 H17B(0.5774) H20A(0.1147) H20B(0.0874) H4(0.1733) H10A(0.4123) H10B(0.3845)
 H7A(-0.0794) H7B(0.04) H6(-0.1544) H13(0.6727) H2(0.0165) H15(0.3172) H1A(-
 0.1496) H12(0.6794) H3(0.1774) H11(0.5071) H16(0.3266)
;
_shelx_res_checksum              99785
_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 1.238
_oxdiff_exptl_absorpt_empirical_full_min 0.874