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_7046190
_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
'C28 H28 Cu N8, 2(C3 H6 O), 2(C F3 O3 S), 1.33(H2 O)'
_chemical_formula_sum            'C36 H42.67 Cu F6 N8 O9.33 S2'
_chemical_formula_weight         978.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-06
_audit_creation_method
;
Olex2 1.2-alpha
(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                 114.487(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.8910(7)
_cell_length_b                   9.2748(2)
_cell_length_c                   25.1344(9)
_cell_measurement_reflns_used    11676
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.9860
_cell_measurement_theta_min      3.8860
_cell_volume                     4432.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (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      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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    -19.00   6.00   0.50    5.00    --    5.00  53.00 -93.00   50
  2  \w    -83.00 -58.00   0.50    5.00    --    0.00  14.00 150.00   50
  3  \w     39.00  88.00   0.50    5.00    --    0.00  14.00 150.00   98
  4  \w     -4.00  85.00   0.50    5.00    --    0.00  43.00   0.00  178
  5  \w    -89.00 -31.00   0.50    5.00    --    0.00  43.00   0.00  116
  6  \w    -89.00  10.00   0.50    5.00    --    0.00  53.00 -93.00  198
  7  \w    -39.00 -14.00   0.50   20.00    --  -90.00  14.00   0.00   50
  8  \w   -124.00 -47.00   0.50   20.00    --  -90.00  14.00   0.00  154
  9  \w   -168.00-142.00   0.50   20.00    --  -90.00  14.00   0.00   52
 10  \w   -173.00  -2.00   0.50   20.00    --  -90.00  29.00 -90.00  342
 11  \w   -164.00-107.00   0.50   20.00    --  -90.00  43.00-120.00  114
 12  \w    -83.00  -5.00   0.50   20.00    --  -90.00  43.00-120.00  156
 13  \w   -130.00 -92.00   0.50   20.00    --  -90.00  43.00 -30.00   76
 14  \w    -71.00 -41.00   0.50   20.00    --  -90.00  43.00 -30.00   60
 15  \w    -27.00  -2.00   0.50   20.00    --  -90.00  43.00 -30.00   50
 16  \w    -90.00 -42.00   0.50   20.00    --  -90.00  53.00 -93.00   96
 17  \w    -40.00 -12.00   0.50   20.00    --  -90.00  60.00-180.00   56
 18  \w    -26.00  -1.00   0.50   20.00    --  -90.00  60.00 -90.00   50
 19  \w   -153.00-115.00   0.50   20.00    --  -90.00  60.00 -90.00   76
 20  \w   -147.00 -75.00   0.50   20.00    --  -90.00  60.00  30.00  144
 21  \w   -179.00 -46.00   0.50   20.00    --  -90.00  60.00-180.00  266
 22  \w   -179.00 -76.00   0.50   20.00    --  -90.00  60.00 -30.00  206
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details 'Rigaku, AFC11 quarter \c goniometer'
_diffrn_measurement_device_type
'Rigaku 007HF equipped with Varimax confocal mirrors and an AFC11 goniometer and HyPix 6000 detector'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0272858000
_diffrn_orient_matrix_UB_12      -0.1311662000
_diffrn_orient_matrix_UB_13      0.0220005000
_diffrn_orient_matrix_UB_21      -0.0720012000
_diffrn_orient_matrix_UB_22      0.0143706000
_diffrn_orient_matrix_UB_23      -0.0523824000
_diffrn_orient_matrix_UB_31      0.0251589000
_diffrn_orient_matrix_UB_32      -0.1009300000
_diffrn_orient_matrix_UB_33      -0.0361852000
_diffrn_radiation_collimation    'Varimax focusing mirrors'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            41244
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_min         3.586
_diffrn_source                   'Rotating anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'Rigaku 007 HF'
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    2.336
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       plate
_exptl_crystal_F_000             2017
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of acetone and water'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.478
_refine_diff_density_min         -1.017
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     616
_refine_ls_number_reflns         8098
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0606
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1259P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1638
_refine_ls_wR_factor_ref         0.1744
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6316
_reflns_number_total             8098
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8dt01256c2.cif
_cod_data_source_block           2017ncs0284za
_cod_depositor_comments
'Adding full bibliography for 7046189--7046200.cif.'
_cod_database_code               7046190
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'Cu2 (C14 H12 N4)2 (C F3 S O3)2'
_chemical_oxdiff_usercomment     EL1464
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.800
_reflns_odcompleteness_completeness 99.65
_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, All O(H,H) groups
2. Others
 Fixed Sof: O61B(0.33333) C61B(0.33333) C62B(0.33333) H62A(0.33333)
 H62B(0.33333) H62C(0.33333) C63B(0.33333) H63A(0.33333) H63B(0.33333)
 H63C(0.33333) O61A(0.66667) C61A(0.66667) C62A(0.66667) H62D(0.66667)
 H62E(0.66667) H62F(0.66667) C63A(0.66667) H63D(0.66667) H63E(0.66667)
 H63F(0.66667) O62B(0.33333) H62G(0.33333) H62H(0.33333)
3.a Free rotating group:
 O62B(H62G,H62H), O101(H10A,H10B)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C11(H11A,H11B), C18(H18A,H18B), C25(H25A,H25B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23),
  C26(H26), C27(H27), C28(H28)
3.d Idealised Me refined as rotating group:
 C62B(H62A,H62B,H62C), C63B(H63A,H63B,H63C), C62A(H62D,H62E,H62F), C63A(H63D,
 H63E,H63F), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C)
;
_shelx_res_checksum              51299
_olex2_date_sample_completion    2017-05-24
_olex2_date_sample_data_collection 2017-05-08
_olex2_date_sample_submission    2017-05-04
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id EL1464
_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 1.439
_oxdiff_exptl_absorpt_empirical_full_min 0.757