#------------------------------------------------------------------------------
#$Date: 2019-11-17 12:34:30 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229900 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/63/7046371.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_7046371
loop_
_publ_author_name
'Mahmoud, Abdallah G.'
'Guedes da Silva, M Fátima C'
'Sokolnicki, Jerzy'
'Smoleński, Piotr'
'Pombeiro, Armando J. L.'
_publ_section_title
;
 Hydrosoluble Cu(i)-DAPTA complexes: synthesis, characterization,
 luminescence thermochromism and catalytic activity for microwave-assisted
 three-component azide-alkyne cycloaddition click reaction.
;
_journal_issue                   21
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7290
_journal_page_last               7299
_journal_paper_doi               10.1039/c8dt01232f
_journal_volume                  47
_journal_year                    2018
_chemical_formula_moiety         'C36 H64 Cu2 I2 N12 O8 P4'
_chemical_formula_sum            'C36 H64 Cu2 I2 N12 O8 P4'
_chemical_formula_weight         1297.75
_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
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-03-29 deposited with the CCDC.
2018-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                107.207(5)
_cell_angle_beta                 98.563(4)
_cell_angle_gamma                99.439(5)
_cell_formula_units_Z            1
_cell_length_a                   7.7429(11)
_cell_length_b                   12.6570(18)
_cell_length_c                   13.3551(19)
_cell_measurement_reflns_used    8647
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.73
_cell_volume                     1205.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1999)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19488
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         2.727
_exptl_absorpt_coefficient_mu    2.356
_exptl_absorpt_correction_T_max  0.819
_exptl_absorpt_correction_T_min  0.728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_description       prism
_exptl_crystal_F_000             652
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_refine_diff_density_max         2.774
_refine_diff_density_min         -1.698
_refine_diff_density_rms         0.238
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4410
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.1208
_refine_ls_R_factor_gt           0.0841
_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/[σ²(Fo²)+(0.0412P)²+29.5995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1779
_refine_ls_wR_factor_ref         0.1978
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3216
_reflns_number_total             4410
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8dt01232f2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7046371.cif.
;
_cod_database_code               7046371
_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   0.650
_shelx_estimated_absorpt_t_max   0.834
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.5426(16) 0.4272(9) 0.2365(8) 0.037(3) Uani 1 1 d . .
H1A H 0.4327 0.4504 0.2503 0.045 Uiso 1 1 calc R U
H1B H 0.6401 0.4934 0.2696 0.045 Uiso 1 1 calc R U
C2 C 0.3978(15) 0.1956(9) 0.2219(8) 0.039(3) Uani 1 1 d . .
H2A H 0.4121 0.1336 0.2490 0.047 Uiso 1 1 calc R U
H2B H 0.2834 0.2133 0.2329 0.047 Uiso 1 1 calc R U
C3 C 0.7581(15) 0.2751(10) 0.2371(9) 0.042(3) Uani 1 1 d . .
H3A H 0.8646 0.3359 0.2634 0.051 Uiso 1 1 calc R U
H3B H 0.7865 0.2102 0.2550 0.051 Uiso 1 1 calc R U
C4 C 0.6754(17) 0.3408(12) 0.0861(10) 0.049(3) Uani 1 1 d . .
H4A H 0.7851 0.3990 0.1118 0.058 Uiso 1 1 calc R U
H4B H 0.6511 0.3156 0.0084 0.058 Uiso 1 1 calc R U
C5 C 0.5643(16) 0.1445(10) 0.0763(10) 0.045(3) Uani 1 1 d . .
H5A H 0.6032 0.0840 0.0981 0.054 Uiso 1 1 calc R U
H5B H 0.5454 0.1217 -0.0012 0.054 Uiso 1 1 calc R U
C6 C 0.2399(15) 0.1299(9) 0.0317(9) 0.037(2) Uani 1 1 d . .
C7 C 0.0697(16) 0.1473(13) 0.0671(11) 0.057(4) Uani 1 1 d . .
H7A H 0.0875 0.2232 0.1153 0.086 Uiso 1 1 calc R U
H7B H 0.0346 0.0943 0.1029 0.086 Uiso 1 1 calc R U
H7C H -0.0224 0.1355 0.0057 0.086 Uiso 1 1 calc R U
C8 C 0.3824(17) 0.3976(9) 0.0559(9) 0.041(3) Uani 1 1 d . .
C9 C 0.371(2) 0.3552(12) -0.0619(9) 0.055(3) Uani 1 1 d . .
H9A H 0.4865 0.3752 -0.0771 0.082 Uiso 1 1 calc R U
H9B H 0.2878 0.3888 -0.0965 0.082 Uiso 1 1 calc R U
H9C H 0.3295 0.2742 -0.0882 0.082 Uiso 1 1 calc R U
C11 C 0.5801(14) 0.2809(9) 0.6952(9) 0.035(2) Uani 1 1 d . .
H11A H 0.5490 0.3498 0.7356 0.042 Uiso 1 1 calc R U
H11B H 0.4694 0.2253 0.6590 0.042 Uiso 1 1 calc R U
C12 C 0.9141(14) 0.3876(9) 0.6832(8) 0.034(2) Uani 1 1 d . .
H12A H 0.9997 0.4050 0.6411 0.041 Uiso 1 1 calc R U
H12B H 0.9007 0.4586 0.7315 0.041 Uiso 1 1 calc R U
C13 C 0.7609(17) 0.1753(9) 0.5310(9) 0.045(3) Uani 1 1 d . .
H13A H 0.6521 0.1179 0.4948 0.054 Uiso 1 1 calc R U
H13B H 0.8268 0.1848 0.4768 0.054 Uiso 1 1 calc R U
C14 C 0.8667(15) 0.3046(10) 0.8196(9) 0.041(3) Uani 1 1 d . .
H14A H 0.8605 0.3790 0.8648 0.049 Uiso 1 1 calc R U
H14B H 0.9227 0.2678 0.8657 0.049 Uiso 1 1 calc R U
C15 C 1.0229(14) 0.2185(9) 0.6812(10) 0.042(3) Uani 1 1 d . .
H15A H 1.0790 0.1828 0.7283 0.051 Uiso 1 1 calc R U
H15B H 1.1102 0.2398 0.6416 0.051 Uiso 1 1 calc R U
C16 C 0.8295(16) 0.0225(11) 0.5897(9) 0.043(3) Uani 1 1 d . .
C17 C 0.9521(17) -0.0231(11) 0.6605(11) 0.051(3) Uani 1 1 d . .
H17A H 0.9693 0.0229 0.7342 0.076 Uiso 1 1 calc R U
H17B H 1.0657 -0.0206 0.6398 0.076 Uiso 1 1 calc R U
H17C H 0.8977 -0.0999 0.6519 0.076 Uiso 1 1 calc R U
C18 C 0.6283(15) 0.1378(10) 0.7836(8) 0.037(2) Uani 1 1 d . .
C19 C 0.4409(17) 0.0713(10) 0.7322(10) 0.048(3) Uani 1 1 d . .
H19A H 0.4087 0.0773 0.6621 0.072 Uiso 1 1 calc R U
H19B H 0.3601 0.1009 0.7754 0.072 Uiso 1 1 calc R U
H19C H 0.4340 -0.0068 0.7260 0.072 Uiso 1 1 calc R U
N1 N 0.5321(13) 0.3901(8) 0.1217(7) 0.040(2) Uani 1 1 d . .
N2 N 0.3931(12) 0.1574(8) 0.1079(7) 0.038(2) Uani 1 1 d . .
N3 N 0.7039(12) 0.2450(8) 0.1215(7) 0.038(2) Uani 1 1 d . .
N4 N 0.6828(12) 0.2385(8) 0.7702(7) 0.036(2) Uani 1 1 d . .
N5 N 0.9813(11) 0.3195(8) 0.7458(7) 0.034(2) Uani 1 1 d . .
N6 N 0.8685(13) 0.1333(8) 0.6036(7) 0.040(2) Uani 1 1 d . .
O1 O 0.2650(14) 0.4376(9) 0.0937(8) 0.065(3) Uani 1 1 d . .
O2 O 0.2419(12) 0.0916(8) -0.0645(7) 0.057(2) Uani 1 1 d . .
O3 O 0.7256(12) 0.1023(8) 0.8417(7) 0.055(2) Uani 1 1 d . .
O4 O 0.7052(14) -0.0437(7) 0.5227(8) 0.065(3) Uani 1 1 d . .
P1 P 0.5773(4) 0.3208(2) 0.3016(2) 0.0310(6) Uani 1 1 d . .
P2 P 0.6977(4) 0.3106(2) 0.5939(2) 0.0283(6) Uani 1 1 d . .
Cu1 Cu 0.57899(18) 0.38696(11) 0.47726(10) 0.0319(3) Uani 1 1 d . .
I1 I 0.23263(10) 0.39538(6) 0.46339(6) 0.0394(2) 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
I I -0.4742 1.8119 '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'
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_3
N1 C1 P1 115.2(7) .
N1 C1 H1A 108.5 .
P1 C1 H1A 108.5 .
N1 C1 H1B 108.5 .
P1 C1 H1B 108.5 .
H1A C1 H1B 107.5 .
N2 C2 P1 115.0(8) .
N2 C2 H2A 108.5 .
P1 C2 H2A 108.5 .
N2 C2 H2B 108.5 .
P1 C2 H2B 108.5 .
H2A C2 H2B 107.5 .
N3 C3 P1 110.1(8) .
N3 C3 H3A 109.6 .
P1 C3 H3A 109.6 .
N3 C3 H3B 109.6 .
P1 C3 H3B 109.6 .
H3A C3 H3B 108.1 .
N1 C4 N3 114.7(9) .
N1 C4 H4A 108.6 .
N3 C4 H4A 108.6 .
N1 C4 H4B 108.6 .
N3 C4 H4B 108.6 .
H4A C4 H4B 107.6 .
N3 C5 N2 114.1(9) .
N3 C5 H5A 108.7 .
N2 C5 H5A 108.7 .
N3 C5 H5B 108.7 .
N2 C5 H5B 108.7 .
H5A C5 H5B 107.6 .
O2 C6 N2 120.7(11) .
O2 C6 C7 120.7(11) .
N2 C6 C7 118.6(10) .
C6 C7 H7A 109.5 .
C6 C7 H7B 109.5 .
H7A C7 H7B 109.5 .
C6 C7 H7C 109.5 .
H7A C7 H7C 109.5 .
H7B C7 H7C 109.5 .
O1 C8 N1 120.6(11) .
O1 C8 C9 121.5(11) .
N1 C8 C9 117.9(11) .
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 .
N4 C11 P2 114.3(7) .
N4 C11 H11A 108.7 .
P2 C11 H11A 108.7 .
N4 C11 H11B 108.7 .
P2 C11 H11B 108.7 .
H11A C11 H11B 107.6 .
N5 C12 P2 110.5(7) .
N5 C12 H12A 109.5 .
P2 C12 H12A 109.5 .
N5 C12 H12B 109.5 .
P2 C12 H12B 109.5 .
H12A C12 H12B 108.1 .
N6 C13 P2 115.8(8) .
N6 C13 H13A 108.3 .
P2 C13 H13A 108.3 .
N6 C13 H13B 108.3 .
P2 C13 H13B 108.3 .
H13A C13 H13B 107.4 .
N5 C14 N4 115.9(9) .
N5 C14 H14A 108.3 .
N4 C14 H14A 108.3 .
N5 C14 H14B 108.3 .
N4 C14 H14B 108.3 .
H14A C14 H14B 107.4 .
N5 C15 N6 115.7(9) .
N5 C15 H15A 108.4 .
N6 C15 H15A 108.4 .
N5 C15 H15B 108.4 .
N6 C15 H15B 108.4 .
H15A C15 H15B 107.4 .
O4 C16 N6 123.2(11) .
O4 C16 C17 118.7(12) .
N6 C16 C17 118.1(10) .
C16 C17 H17A 109.5 .
C16 C17 H17B 109.5 .
H17A C17 H17B 109.5 .
C16 C17 H17C 109.5 .
H17A C17 H17C 109.5 .
H17B C17 H17C 109.5 .
O3 C18 N4 121.5(11) .
O3 C18 C19 119.3(11) .
N4 C18 C19 119.0(10) .
C18 C19 H19A 109.5 .
C18 C19 H19B 109.5 .
H19A C19 H19B 109.5 .
C18 C19 H19C 109.5 .
H19A C19 H19C 109.5 .
H19B C19 H19C 109.5 .
C8 N1 C4 125.5(10) .
C8 N1 C1 118.5(10) .
C4 N1 C1 115.8(9) .
C6 N2 C2 123.4(9) .
C6 N2 C5 120.3(9) .
C2 N2 C5 116.3(9) .
C5 N3 C3 112.0(9) .
C5 N3 C4 115.7(9) .
C3 N3 C4 113.6(9) .
C18 N4 C11 124.1(9) .
C18 N4 C14 119.8(9) .
C11 N4 C14 115.5(8) .
C15 N5 C14 115.9(9) .
C15 N5 C12 113.1(9) .
C14 N5 C12 110.5(8) .
C16 N6 C13 118.1(9) .
C16 N6 C15 126.1(10) .
C13 N6 C15 115.6(9) .
C3 P1 C1 96.8(5) .
C3 P1 C2 97.2(5) .
C1 P1 C2 103.7(5) .
C3 P1 Cu1 128.3(4) .
C1 P1 Cu1 111.4(3) .
C2 P1 Cu1 115.7(4) .
C12 P2 C11 97.9(5) .
C12 P2 C13 98.3(5) .
C11 P2 C13 103.3(6) .
C12 P2 Cu1 118.0(4) .
C11 P2 Cu1 121.5(3) .
C13 P2 Cu1 114.1(4) .
P2 Cu1 P1 122.65(11) .
P2 Cu1 I1 117.43(9) .
P1 Cu1 I1 98.58(9) .
P2 Cu1 I1 106.90(8) 2_666
P1 Cu1 I1 102.87(8) 2_666
I1 Cu1 I1 106.70(5) 2_666
Cu1 I1 Cu1 73.30(5) 2_666
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.450(13) .
C1 P1 1.839(11) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C2 N2 1.448(14) .
C2 P1 1.849(11) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 N3 1.453(14) .
C3 P1 1.834(12) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 N1 1.434(15) .
C4 N3 1.461(16) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 N3 1.433(15) .
C5 N2 1.469(15) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 O2 1.236(14) .
C6 N2 1.364(14) .
C6 C7 1.492(17) .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 O1 1.215(15) .
C8 N1 1.381(15) .
C8 C9 1.487(16) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C11 N4 1.464(13) .
C11 P2 1.832(11) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 N5 1.469(13) .
C12 P2 1.834(10) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 N6 1.458(14) .
C13 P2 1.851(11) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 N5 1.452(14) .
C14 N4 1.472(14) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 N5 1.431(14) .
C15 N6 1.487(14) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 O4 1.210(14) .
C16 N6 1.335(15) .
C16 C17 1.537(16) .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 O3 1.230(13) .
C18 N4 1.347(14) .
C18 C19 1.499(16) .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
P1 Cu1 2.243(3) .
P2 Cu1 2.227(3) .
Cu1 I1 2.6824(15) .
Cu1 I1 2.7187(15) 2_666
I1 Cu1 2.7186(15) 2_666
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C5 H5A O2 0.97 2.65 3.531(15) 151.1 2_655
C7 H7C O3 0.96 2.59 3.548(16) 179.1 1_454
C9 H9C O2 0.96 2.43 3.309(17) 153.0 .
C12 H12A I1 0.97 3.17 4.119(11) 164.8 1_655
C14 H14A O1 0.97 2.60 3.497(16) 153.4 2_666
C19 H19A O4 0.96 2.38 3.318(16) 165.7 2_656
C19 H19B O2 0.96 2.47 3.283(16) 141.9 1_556
