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_7046197
_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         'C16 H15 N3 O'
_chemical_formula_sum            'C16 H15 N3 O'
_chemical_formula_weight         265.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_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                 92.836(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.1339(8)
_cell_length_b                   5.6565(6)
_cell_length_c                   14.5299(16)
_cell_measurement_reflns_used    532
_cell_measurement_temperature    173
_cell_measurement_theta_max      69.0420
_cell_measurement_theta_min      5.4530
_cell_volume                     667.69(12)
_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 0.984
_diffrn_measured_fraction_theta_max 0.971
_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     -9.00  17.00   1.00    2.00    --    0.00 -77.00 -60.00   26
  2  \w    -64.00 -39.00   1.00    2.00    --    0.00 -77.00 -60.00   25
  3  \w   -127.00 -29.00   1.00    3.80    --  -54.75 -77.00  30.00   98
  4  \w    -72.00  16.00   1.00    3.80    --  -54.75  57.00 150.00   88
  5  \w     84.00 126.00   1.00    3.80    --   54.75 125.00   0.00   42
  6  \w     79.00 110.00   1.00    3.80    --   54.75  99.00  40.00   31
  7  \w     83.00 175.00   1.00    3.80    --  109.50  64.00 -90.00   92
  8  \w     64.00 133.00   1.00    3.80    --  109.50 -50.00 -30.00   69
  9  \w     62.00  90.00   1.00    3.80    --  109.50-111.00  30.00   28
 10  \w     55.00  87.00   1.00    3.80    --  109.50-111.00   0.00   32
 11  \w     39.00 139.00   1.00    3.80    --  109.50 -38.00 -90.00  100
 12  \w     39.00 133.00   1.00    3.80    --  109.50 -50.00 120.00   94
;
_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      0.0359961000
_diffrn_orient_matrix_UB_12      0.0968786000
_diffrn_orient_matrix_UB_13      0.0980139000
_diffrn_orient_matrix_UB_21      0.1808163000
_diffrn_orient_matrix_UB_22      0.0425617000
_diffrn_orient_matrix_UB_23      -0.0223163000
_diffrn_orient_matrix_UB_31      -0.0444742000
_diffrn_orient_matrix_UB_32      0.2509551000
_diffrn_orient_matrix_UB_33      -0.0341060000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            1972
_diffrn_reflns_point_group_measured_fraction_full 0.643
_diffrn_reflns_point_group_measured_fraction_max 0.632
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.243
_diffrn_reflns_theta_min         5.445
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70135
_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    1.320
_exptl_crystal_description       needle
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0069(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         1586
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0550P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1164
_reflns_Friedel_coverage         0.176
_reflns_Friedel_fraction_full    0.219
_reflns_Friedel_fraction_max     0.212
_reflns_number_gt                1263
_reflns_number_total             1586
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8dt01256c2.cif
_cod_data_source_block           cu230
_cod_depositor_comments
'Adding full bibliography for 7046189--7046200.cif.'
_cod_database_code               7046197
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C16H15N3O
_reflns_odcompleteness_completeness 98.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C5(H5), C12(H12), C1(H1), C2(H2), C3(H3), C11(H11),
 C4(H4), C8(H8)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              21077
_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 1.485
_oxdiff_exptl_absorpt_empirical_full_min 0.673