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_7046193
_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(C41 H32 Cu2 F3 N12 O3 S), 2(C F3 O3 S), 4(C3 H6 O)'
_chemical_formula_sum            'C96 H88 Cu4 F12 N24 O16 S4'
_chemical_formula_weight         2444.30
_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     dual
_audit_creation_date             2018-01-24
_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                90.7040(10)
_cell_angle_beta                 90.0420(10)
_cell_angle_gamma                97.2670(10)
_cell_formula_units_Z            2
_cell_length_a                   16.6451(3)
_cell_length_b                   17.1433(2)
_cell_length_c                   19.1060(3)
_cell_measurement_reflns_used    18045
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.7290
_cell_measurement_theta_min      3.4820
_cell_volume                     5407.72(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.31c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31c (Rigaku OD, 2017)'
_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 0.956
_diffrn_measured_fraction_theta_max 0.956
_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    -84.00  70.00   0.50    5.00    --    5.00  29.00 -30.00  308
  2  \w    -19.00   6.00   0.50    5.00    --    5.00  41.00-157.00   50
  3  \w    -89.00  80.00   0.50    5.00    --    0.00  41.00-157.00  338
  4  \w    -82.00 -56.00   0.50    5.00    --    0.00  60.00-120.00   52
  5  \w   -153.00-127.00   0.50   20.00    --  -90.00   0.00-180.00   52
  6  \w   -108.00 -82.00   0.50   20.00    --  -90.00   0.00-180.00   52
  7  \w   -178.00 -85.00   0.50   20.00    --  -90.00  14.00-150.00  186
  8  \w    -68.00 -37.00   0.50   20.00    --  -90.00  14.00-150.00   62
  9  \w   -179.00-148.00   0.50   20.00    --  -90.00  29.00   0.00   62
 10  \w   -142.00  -1.00   0.50   20.00    --  -90.00  29.00   0.00  282
 11  \w   -114.00 -89.00   0.50   20.00    --  -90.00  41.00-157.00   50
 12  \w   -124.00 -98.00   0.50   20.00    --  -90.00  43.00 120.00   52
 13  \w   -110.00 -85.00   0.50   20.00    --  -90.00  60.00-180.00   50
 14  \w   -179.00 -96.00   0.50   20.00    --  -90.00  60.00 -60.00  166
 15  \w    -77.00 -17.00   0.50   20.00    --  -90.00  60.00 -60.00  120
 16  \w   -149.00-116.00   0.50   20.00    --  -90.00  60.00-180.00   66
 17  \w    -71.00 -17.00   0.50   20.00    --  -90.00  60.00-180.00  108
 18  \w   -178.00  -1.00   0.50   20.00    --  -90.00  60.00  90.00  354
 19  \w    -52.00  -4.00   0.50   20.00    --  -90.00  60.00 -90.00   96
 20  \w   -135.00 -95.00   0.50   20.00    --  -90.00  60.00 -90.00   80
;
_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      0.0217552000
_diffrn_orient_matrix_UB_12      0.0867059000
_diffrn_orient_matrix_UB_13      -0.0205630000
_diffrn_orient_matrix_UB_21      0.0748202000
_diffrn_orient_matrix_UB_22      0.0065364000
_diffrn_orient_matrix_UB_23      0.0482350000
_diffrn_orient_matrix_UB_31      0.0513243000
_diffrn_orient_matrix_UB_32      -0.0254447000
_diffrn_orient_matrix_UB_33      -0.0612628000
_diffrn_radiation_collimation    'Varimax focusing mirrors'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            50455
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        66.590
_diffrn_reflns_theta_max         66.590
_diffrn_reflns_theta_min         3.458
_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    2.420
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.31c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_description       plate
_exptl_crystal_F_000             2496
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of acetone and Et2O'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.063
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1442
_refine_ls_number_reflns         18266
_refine_ls_number_restraints     1296
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0609
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1242P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1626
_refine_ls_wR_factor_ref         0.1769
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13560
_reflns_number_total             18266
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8dt01256c2.cif
_cod_data_source_block           2017ncs0287xa
_cod_depositor_comments
'Adding full bibliography for 7046189--7046200.cif.'
_cod_database_code               7046193
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'Cu (C20 H16 N3)2 C F3 S O3'
_chemical_oxdiff_usercomment     EL1460A
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.760
_reflns_odcompleteness_completeness 95.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Others
 Fixed Sof: C243(0.5) H24D(0.5) H24E(0.5) H24F(0.5) C253(0.5) H25A(0.5)
 H25B(0.5) H25C(0.5)
 Fixed Uiso: H29(0.041) H7A(0.043) H7B(0.043) H22(0.047) H30(0.045)
 H27A(0.041) H27B(0.041) H57A(0.044) H57B(0.044) H16(0.049) H59(0.051)
 H32(0.047) H9(0.049) H12(0.05) H31(0.046) H25(0.053) H34A(0.048) H34B(0.048)
 H14A(0.041) H14B(0.041) H17(0.053) H77A(0.044) H77B(0.044) H5(0.055)
 H64A(0.046) H64B(0.046) H10(0.056) H66(0.052) H52(0.057) H79(0.049) H69(0.047)
 H19(0.051) H89(0.055) H67(0.057) H68(0.056) H24(0.061) H18(0.054) H36(0.059)
 H2(0.057) H80(0.057) H11(0.055) H23(0.059) H62(0.055) H84A(0.048) H84B(0.048)
 H81(0.061) H82(0.055) H86(0.06) H72(0.058) H87(0.065) H60(0.063) H4(0.064)
 H3(0.064) H55(0.053) H61(0.064) H88(0.063) H54(0.063) H39(0.065) H53(0.066)
 H37(0.065) H38(0.071) H75(0.07) H73(0.077) H74(0.084) H26A(0.108) H26B(0.108)
 H26C(0.108) H22A(0.104) H22B(0.104) H22C(0.104) H26D(0.211) H26E(0.211)
 H26F(0.211) H20A(0.224) H20B(0.224) H20C(0.224) H22D(0.144) H22E(0.144)
 H22F(0.144) H20D(0.277) H20E(0.277) H20F(0.277) H23A(0.138) H23B(0.138)
 H23C(0.138) H23D(0.161) H23E(0.161) H23F(0.161) H24A(0.217) H24B(0.217)
 H24C(0.217) H24D(0.216) H24E(0.216) H24F(0.216) H25A(0.295) H25B(0.295)
 H25C(0.295)
 Fixed X: H29(0.138859) H7A(-0.094438) H7B(-0.13968) H22(0.234299)
 H30(0.14362) H27A(0.091915) H27B(0.005455) H57A(0.377336) H57B(0.431668)
 H16(0.020819) H59(0.262314) H32(0.007057) H9(-0.025473) H12(0.128143)
 H31(0.076069) H25(0.235539) H34A(-0.032045) H34B(0.028414) H14A(-0.046521)
 H14B(-0.043058) H17(0.079332) H77A(0.369436) H77B(0.300725) H5(-0.206266)
 H64A(0.408701) H64B(0.333984) H10(0.099119) H66(0.252058) H52(0.368212)
 H79(0.450654) H69(0.382611) H19(0.200721) H89(0.528812) H67(0.224536)
 H68(0.287755) H24(0.344166) H18(0.16753) H36(-0.136008) H2(-0.265697)
 H80(0.53853) H11(0.173847) H23(0.342508) H62(0.225481) H84A(0.31145)
 H84B(0.353105) H81(0.552945) H82(0.477467) H86(0.418906) H72(0.352377)
 H87(0.494003) H60(0.152752) H4(-0.284512) H3(-0.315463) H55(0.287237)
 H61(0.1337) H88(0.548661) H54(0.245857) H39(-0.308972) H53(0.284664) H37(-
 0.267943) H38(-0.35194) H75(0.226126) H73(0.235099) H74(0.171434) H26A(-
 0.349429) H26B(-0.408095) H26C(-0.399091) H22A(0.647731) H22B(0.615564)
 H22C(0.592689) H26D(-0.318712) H26E(-0.376376) H26F(-0.282479) H20A(0.882346)
 H20B(0.859383) H20C(0.934854) H22D(0.444191) H22E(0.476875) H22F(0.411746)
 H20D(1.033204) H20E(0.944015) H20F(1.004468) H23A(0.455772) H23B(0.540786)
 H23C(0.536876) H23D(0.561854) H23E(0.465805) H23F(0.511733) H24A(0.112694)
 H24B(0.114391) H24C(0.072227) H24D(-0.055098) H24E(-0.107918) H24F(-0.079068)
 H25A(-0.020186) H25B(-0.005208) H25C(-0.089724)
 Fixed Y: H29(0.720596) H7A(0.446434) H7B(0.407698) H22(0.437245)
 H30(0.827679) H27A(0.710625) H27B(0.677116) H57A(0.875041) H57B(0.916999)
 H16(0.176713) H59(0.828851) H32(0.936039) H9(0.559491) H12(0.35356)
 H31(0.934669) H25(0.680222) H34A(0.776654) H34B(0.853432) H14A(0.290781)
 H14B(0.350812) H17(0.059388) H77A(0.835599) H77B(0.863752) H5(0.448141)
 H64A(1.008145) H64B(1.011065) H10(0.557176) H66(1.104552) H52(0.563712)
 H79(0.990121) H69(1.358325) H19(0.122678) H89(0.501848) H67(1.219009)
 H68(1.342776) H24(0.606868) H18(0.033975) H36(1.091483) H2(0.708259)
 H80(0.982056) H11(0.452913) H23(0.487144) H62(1.07732) H84A(0.723695)
 H84B(0.732863) H81(0.859265) H82(0.746408) H86(0.485716) H72(1.183896)
 H87(0.391163) H60(0.888351) H4(0.512849) H3(0.639116) H55(0.744557)
 H61(1.012757) H88(0.398765) H54(0.609197) H39(0.880175) H53(0.521932)
 H37(1.105176) H38(1.001269) H75(0.979195) H73(1.198249) H74(1.096414)
 H26A(0.437503) H26B(0.376525) H26C(0.362129) H22A(0.817296) H22B(0.765741)
 H22C(0.734651) H26D(0.219697) H26E(0.240607) H26F(0.235617) H20A(0.766859)
 H20B(0.815577) H20C(0.766379) H22D(0.727546) H22E(0.778328) H22F(0.80975)
 H20D(0.919789) H20E(0.94514) H20F(0.978122) H23A(0.831979) H23B(0.802294)
 H23C(0.893054) H23D(0.720601) H23E(0.719749) H23F(0.745311) H24A(0.794148)
 H24B(0.703486) H24C(0.759156) H24D(0.736634) H24E(0.735783) H24F(0.656027)
 H25A(0.833116) H25B(0.849099) H25C(0.803824)
 Fixed Z: H29(0.000147) H7A(0.096478) H7B(0.16379) H22(0.051104) H30(-
 0.074719) H27A(0.167812) H27B(0.135846) H57A(0.349304) H57B(0.411352)
 H16(0.19873) H59(0.492598) H32(0.06015) H9(0.239811) H12(0.198928) H31(-
 0.044408) H25(0.176412) H34A(0.177198) H34B(0.198207) H14A(0.151262)
 H14B(0.087708) H17(0.193218) H77A(0.608725) H77B(0.658024) H5(0.28084)
 H64A(0.353647) H64B(0.301593) H10(0.297777) H66(0.241696) H52(0.485847)
 H79(0.715613) H69(0.309992) H19(0.014545) H89(0.627395) H67(0.185862)
 H68(0.220044) H24(0.182157) H18(0.10483) H36(0.208613) H2(0.236749)
 H80(0.809606) H11(0.278734) H23(0.12341) H62(0.41131) H84A(0.735736)
 H84B(0.660383) H81(0.85692) H82(0.811901) H86(0.859128) H72(0.537824)
 H87(0.815354) H60(0.530553) H4(0.357543) H3(0.335814) H55(0.318378)
 H61(0.488871) H88(0.702236) H54(0.308967) H39(0.100899) H53(0.391019)
 H37(0.174654) H38(0.125024) H75(0.68247) H73(0.600493) H74(0.669288)
 H26A(0.031663) H26B(0.076975) H26C(-0.005409) H22A(0.276031) H22B(0.208967)
 H22C(0.285949) H26D(0.02327) H26E(0.085927) H26F(0.100472) H20A(0.571633)
 H20B(0.639117) H20C(0.641791) H22D(0.228561) H22E(0.162377) H22F(0.213642)
 H20D(0.65862) H20E(0.662562) H20F(0.601639) H23A(0.168154) H23B(0.14994)
 H23C(0.168349) H23D(0.261123) H23E(0.255617) H23F(0.32749) H24A(0.355615)
 H24B(0.373767) H24C(0.426389) H24D(0.425621) H24E(0.355531) H24F(0.383105)
 H25A(0.396042) H25B(0.314452) H25C(0.340377)
;
_shelx_res_checksum              96397
_shelx_fab_checksum              65196
_olex2_date_sample_data_collection 2017-05-10
_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 EL1460A
_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 1.587
_oxdiff_exptl_absorpt_empirical_full_min 0.773