#------------------------------------------------------------------------------
#$Date: 2025-10-06 11:30:03 +0200 (Mon 06 de Oct de 2025) $
#$Revision: 302655 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/54/1575433.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1575433
loop_
_publ_author_name
'Cruz, Tiago F. C.'
'López-Sánchez, Belén'
'Lemos, M Amélia N D A'
'Romerosa, Antonio'
'Martins, Luísa M D R S'
_publ_section_title
;
 Borane-functionalized heteroscorpionate copper complexes as catalysts for
 azide-alkyne cycloaddition.
;
_journal_issue                   36
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              13472
_journal_page_last               13482
_journal_paper_doi               10.1039/d5dt01595b
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C14 H20 Cl Cu N4'
_chemical_formula_sum            'C14 H20 Cl Cu N4'
_chemical_formula_weight         343.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-08-12 deposited with the CCDC.	2025-08-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 119.745(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.393(3)
_cell_length_b                   25.453(9)
_cell_length_c                   7.699(2)
_cell_measurement_reflns_used    1362
_cell_measurement_temperature    150
_cell_measurement_theta_max      23.14
_cell_measurement_theta_min      2.62
_cell_volume                     1598.2(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    enCIFer
_computing_publication_material  Mercury
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXL-2019/2 (Sheldrick, 2019)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0815
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4537
_diffrn_reflns_point_group_measured_fraction_full 0.840
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_theta_full        26.444
_diffrn_reflns_theta_max         26.444
_diffrn_reflns_theta_min         2.622
_exptl_absorpt_coefficient_mu    1.529
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.039(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.889
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2764
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.889
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0352
_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/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0541
_refine_ls_wR_factor_ref         0.0575
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    0.689
_reflns_Friedel_fraction_max     0.689
_reflns_number_gt                2207
_reflns_number_total             2764
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5dt01595b3.cif
_cod_data_source_block           1a
_cod_depositor_comments
'Adding full bibliography for 1575433--1575435.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               1575433
_shelx_shelxl_version_number     2019/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.580
_shelx_estimated_absorpt_t_max   0.941
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.30930(7) 0.60059(3) 0.38628(8) 0.02846(18) Uani 1 1 d . . . . .
Cl1 Cl 0.05002(15) 0.61744(6) 0.22745(18) 0.0342(4) Uani 1 1 d . . . . .
N4 N 0.6199(4) 0.55156(16) 0.6904(5) 0.0207(10) Uani 1 1 d . . . . .
N1 N 0.4997(4) 0.64263(16) 0.4031(5) 0.0217(10) Uani 1 1 d . . . . .
N3 N 0.4561(4) 0.54273(16) 0.5610(6) 0.0242(11) Uani 1 1 d . . . . .
C14 C 0.5826(8) 0.7349(3) 0.7874(9) 0.0524(18) Uani 1 1 d . . . . .
H14A H 0.470441 0.731516 0.701125 0.063 Uiso 1 1 calc R U . . .
H14B H 0.630906 0.767997 0.816535 0.063 Uiso 1 1 calc R U . . .
N2 N 0.6578(4) 0.63076(17) 0.5484(5) 0.0199(10) Uani 1 1 d . . . . .
C7 C 0.5880(5) 0.4661(2) 0.6812(7) 0.0229(12) Uani 1 1 d . . . . .
H7 H 0.607056 0.430241 0.703771 0.027 Uiso 1 1 calc R U . . .
C9 C 0.8813(6) 0.5026(2) 0.9143(7) 0.0289(15) Uani 1 1 d . . . . .
H9A H 0.940958 0.523775 0.868927 0.043 Uiso 1 1 calc R U . . .
H9B H 0.917175 0.466768 0.927386 0.043 Uiso 1 1 calc R U . . .
H9C H 0.900784 0.515274 1.041739 0.043 Uiso 1 1 calc R U . . .
C6 C 0.4372(6) 0.4908(2) 0.5538(7) 0.0230(12) Uani 1 1 d . . . . .
C1 C 0.5178(6) 0.6724(2) 0.2730(7) 0.0234(13) Uani 1 1 d . . . . .
C13 C 0.6727(7) 0.6930(2) 0.8680(7) 0.0289(14) Uani 1 1 d . . . . .
H13 H 0.784402 0.697956 0.953536 0.035 Uiso 1 1 calc R U . . .
C12 C 0.6092(6) 0.6379(2) 0.8327(7) 0.0253(13) Uani 1 1 d . . . . .
H12A H 0.490799 0.638347 0.749711 0.030 Uiso 1 1 calc R U . . .
H12B H 0.636046 0.621829 0.959637 0.030 Uiso 1 1 calc R U . . .
C5 C 0.3669(6) 0.6923(2) 0.0864(7) 0.0359(15) Uani 1 1 d . . . . .
H5A H 0.352642 0.672622 -0.027645 0.054 Uiso 1 1 calc R U . . .
H5B H 0.380550 0.728797 0.067335 0.054 Uiso 1 1 calc R U . . .
H5C H 0.272073 0.687876 0.101442 0.054 Uiso 1 1 calc R U . . .
C2 C 0.6846(7) 0.6801(2) 0.3326(7) 0.0247(13) Uani 1 1 d . . . . .
H2 H 0.727485 0.699132 0.265942 0.030 Uiso 1 1 calc R U . . .
C4 C 0.9517(5) 0.6490(2) 0.6471(7) 0.0331(15) Uani 1 1 d . . . . .
H4A H 0.982914 0.668543 0.767414 0.050 Uiso 1 1 calc R U . . .
H4B H 1.007154 0.663036 0.580914 0.050 Uiso 1 1 calc R U . . .
H4C H 0.981428 0.612797 0.679941 0.050 Uiso 1 1 calc R U . . .
C11 C 0.6822(5) 0.60515(19) 0.7310(6) 0.0205(12) Uani 1 1 d . . . . .
H11 H 0.800729 0.603154 0.822813 0.025 Uiso 1 1 calc R U . . .
C3 C 0.7709(5) 0.6532(2) 0.5120(7) 0.0227(12) Uani 1 1 d . . . . .
C10 C 0.2748(6) 0.4657(2) 0.4205(8) 0.0373(16) Uani 1 1 d . . . . .
H10A H 0.193576 0.492440 0.353650 0.056 Uiso 1 1 calc R U . . .
H10B H 0.244118 0.444260 0.499242 0.056 Uiso 1 1 calc R U . . .
H10C H 0.282572 0.444202 0.323015 0.056 Uiso 1 1 calc R U . . .
C8 C 0.7005(6) 0.5057(2) 0.7650(7) 0.0215(13) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Cu1 N1 93.06(16) . . ?
N3 Cu1 Cl1 137.02(12) . . ?
N1 Cu1 Cl1 129.91(12) . . ?
C8 N4 N3 110.8(4) . . ?
C8 N4 C11 129.5(4) . . ?
N3 N4 C11 119.7(4) . . ?
C1 N1 N2 104.3(4) . . ?
C1 N1 Cu1 133.5(3) . . ?
N2 N1 Cu1 119.7(3) . . ?
C6 N3 N4 105.7(4) . . ?
C6 N3 Cu1 131.8(3) . . ?
N4 N3 Cu1 121.0(3) . . ?
C13 C14 H14A 120.0 . . ?
C13 C14 H14B 120.0 . . ?
H14A C14 H14B 120.0 . . ?
C3 N2 N1 112.4(4) . . ?
C3 N2 C11 128.5(4) . . ?
N1 N2 C11 118.1(4) . . ?
C8 C7 C6 105.9(5) . . ?
C8 C7 H7 127.0 . . ?
C6 C7 H7 127.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C6 C7 110.3(4) . . ?
N3 C6 C10 121.5(4) . . ?
C7 C6 C10 128.1(5) . . ?
N1 C1 C2 111.7(4) . . ?
N1 C1 C5 119.5(5) . . ?
C2 C1 C5 128.8(5) . . ?
C14 C13 C12 124.9(5) . . ?
C14 C13 H13 117.6 . . ?
C12 C13 H13 117.6 . . ?
C13 C12 C11 111.5(4) . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C2 C1 105.2(5) . . ?
C3 C2 H2 127.4 . . ?
C1 C2 H2 127.4 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N4 C11 N2 110.9(4) . . ?
N4 C11 C12 112.8(4) . . ?
N2 C11 C12 110.8(4) . . ?
N4 C11 H11 107.3 . . ?
N2 C11 H11 107.3 . . ?
C12 C11 H11 107.3 . . ?
N2 C3 C2 106.5(4) . . ?
N2 C3 C4 124.4(4) . . ?
C2 C3 C4 129.1(5) . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N4 C8 C7 107.2(4) . . ?
N4 C8 C9 123.3(5) . . ?
C7 C8 C9 129.5(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N3 2.010(4) . ?
Cu1 N1 2.032(4) . ?
Cu1 Cl1 2.1577(15) . ?
N4 C8 1.355(6) . ?
N4 N3 1.375(5) . ?
N4 C11 1.456(6) . ?
N1 C1 1.333(6) . ?
N1 N2 1.378(5) . ?
N3 C6 1.331(6) . ?
C14 C13 1.309(7) . ?
C14 H14A 0.9300 . ?
C14 H14B 0.9300 . ?
N2 C3 1.352(6) . ?
N2 C11 1.460(6) . ?
C7 C8 1.368(7) . ?
C7 C6 1.409(6) . ?
C7 H7 0.9300 . ?
C9 C8 1.508(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C6 C10 1.495(6) . ?
C1 C2 1.411(7) . ?
C1 C5 1.519(6) . ?
C13 C12 1.497(7) . ?
C13 H13 0.9300 . ?
C12 C11 1.520(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C2 C3 1.387(7) . ?
C2 H2 0.9300 . ?
C4 C3 1.492(6) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C11 H11 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
