#------------------------------------------------------------------------------
#$Date: 2023-05-05 05:07:12 +0300 (Fri, 05 May 2023) $
#$Revision: 283287 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/18/7711848.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_7711848
loop_
_publ_author_name
'Heydari, Neda'
'Bikas, Rahman'
'Siczek, Milosz'
'Lis, Tadeusz'
_publ_section_title
;
 Green carbon-carbon homocoupling of terminal alkynes by a silica
 supported Cu(II)-hydrazone coordination compound.
;
_journal_issue                   2
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              421
_journal_page_last               433
_journal_paper_doi               10.1039/d2dt03054c
_journal_volume                  52
_journal_year                    2023
_chemical_formula_moiety         'C16 H18 Cu N4 O7, C H4 O'
_chemical_formula_sum            'C17 H22 Cu N4 O8'
_chemical_formula_weight         473.92
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2022-09-19 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                98.42(5)
_cell_angle_beta                 105.98(5)
_cell_angle_gamma                107.55(5)
_cell_formula_units_Z            2
_cell_length_a                   7.814(2)
_cell_length_b                   11.098(3)
_cell_length_c                   12.616(4)
_cell_measurement_reflns_used    4766
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.8
_cell_volume                     970.9(7)
_computing_cell_refinement       'CrysAlis RED; Oxford-Diffraction Poland, 2003'
_computing_data_collection       'CrysAlis CCD; Oxford-Diffraction Poland, 2003'
_computing_data_reduction        'CrysAlis RED; Oxford-Diffraction Poland, 2003'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type
;
Kuma KM4 kappa-geometry diffractometer with a CCD detector
;
_diffrn_measurement_method       w/
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9665
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         27.997
_diffrn_reflns_theta_min         2.835
_exptl_absorpt_coefficient_mu    1.180
_exptl_absorpt_correction_T_max  0.897
_exptl_absorpt_correction_T_min  0.591
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_description       block
_exptl_crystal_F_000             490
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.832
_refine_diff_density_min         -1.191
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4428
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0560
_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/[σ²(Fo²)+(0.1000P)²+0.6156P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1481
_refine_ls_wR_factor_ref         0.1583
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3888
_reflns_number_total             4428
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt03054c2.cif
_cod_data_source_block           pa102a
_cod_depositor_comments
'Adding full bibliography for 7711848--7711849.cif.'
_cod_original_cell_volume        970.9(6)
_cod_database_code               7711848
_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   0.563
_shelx_estimated_absorpt_t_max   0.891
_shelxl_version_number           2013-2
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.35309(5) 0.71185(3) 0.60657(3) 0.01905(15) Uani 1 1 d . . . . .
O2 O 0.4530(3) 0.60388(19) 0.68879(18) 0.0205(4) Uani 1 1 d . . . . .
C1 C 0.3222(4) 0.4073(3) 0.5349(2) 0.0172(5) Uani 1 1 d . . . . .
C2 C 0.4339(4) 0.4821(3) 0.6470(3) 0.0185(6) Uani 1 1 d . . . . .
C3 C 0.3171(4) 0.2783(3) 0.4987(3) 0.0202(6) Uani 1 1 d . . . . .
H3 H 0.2431 0.2290 0.4227 0.024 Uiso 1 1 calc R U . . .
C4 C 0.4180(5) 0.2244(3) 0.5721(3) 0.0226(6) Uani 1 1 d . . . . .
H4 H 0.4143 0.1384 0.5467 0.027 Uiso 1 1 calc R U . . .
C5 C 0.5262(4) 0.2958(3) 0.6843(3) 0.0206(6) Uani 1 1 d . . . . .
H5 H 0.5948 0.2580 0.7353 0.025 Uiso 1 1 calc R U . . .
C6 C 0.5334(4) 0.4215(3) 0.7210(3) 0.0197(6) Uani 1 1 d . . . . .
O6 O 0.6327(3) 0.4988(2) 0.82903(18) 0.0246(5) Uani 1 1 d . . . . .
C7 C 0.2100(4) 0.4546(3) 0.4529(2) 0.0185(5) Uani 1 1 d . . . . .
H7 H 0.1391 0.3990 0.3788 0.022 Uiso 1 1 calc R U . . .
N1 N 0.2008(4) 0.5699(2) 0.4752(2) 0.0187(5) Uani 1 1 d . . . . .
N2 N 0.0868(4) 0.6068(2) 0.3918(2) 0.0185(5) Uani 1 1 d . . . . .
H2 H 0.0072 0.5517 0.3269 0.066(16) Uiso 1 1 calc R . . . .
C8 C 0.1065(4) 0.7338(3) 0.4169(2) 0.0186(6) Uani 1 1 d . . . . .
O1 O 0.2225(3) 0.80623(19) 0.51330(17) 0.0198(4) Uani 1 1 d . . . . .
C11 C -0.0025(4) 0.7848(3) 0.3338(2) 0.0180(5) Uani 1 1 d . . . . .
C21 C -0.1202(4) 0.7101(3) 0.2238(3) 0.0207(6) Uani 1 1 d . . . . .
H21 H -0.1322 0.6216 0.2015 0.025 Uiso 1 1 calc R U . . .
C31 C -0.2191(4) 0.7630(3) 0.1472(2) 0.0205(6) Uani 1 1 d . . . . .
H31 H -0.2978 0.7105 0.0729 0.025 Uiso 1 1 calc R U . . .
C41 C -0.2047(4) 0.8943(3) 0.1779(2) 0.0183(6) Uani 1 1 d . . . . .
C51 C -0.0885(4) 0.9695(3) 0.2893(3) 0.0199(6) Uani 1 1 d . . . . .
H51 H -0.0787 1.0574 0.3123 0.024 Uiso 1 1 calc R U . . .
C61 C 0.0106(4) 0.9159(3) 0.3646(2) 0.0191(6) Uani 1 1 d . . . . .
H61 H 0.0894 0.9681 0.4390 0.023 Uiso 1 1 calc R U . . .
N3 N -0.3035(4) 0.9451(2) 0.1025(2) 0.0231(5) Uani 1 1 d . . . . .
H3A H -0.3628 0.8921 0.0308 0.048(13) Uiso 1 1 d R . . . .
H3B H -0.2985 1.0292 0.1153 0.050(13) Uiso 1 1 d R . . . .
C9 C 0.7348(5) 0.4448(3) 0.9096(3) 0.0287(7) Uani 1 1 d . . . . .
H9A H 0.6455 0.3656 0.9173 0.043 Uiso 1 1 calc R U . . .
H9B H 0.7977 0.5088 0.9836 0.043 Uiso 1 1 calc R U . . .
H9C H 0.8310 0.4230 0.8830 0.043 Uiso 1 1 calc R U . . .
O3 O 0.1799(3) 0.7414(2) 0.73000(18) 0.0236(5) Uani 1 1 d . . . . .
N4 N 0.2074(4) 0.7026(2) 0.8210(2) 0.0197(5) Uani 1 1 d . . . . .
O4 O 0.1211(3) 0.5861(2) 0.81756(19) 0.0263(5) Uani 1 1 d . . . . .
O5 O 0.3145(3) 0.7810(2) 0.9132(2) 0.0288(5) Uani 1 1 d . . . . .
O1M O 0.5694(3) 0.86483(19) 0.70890(18) 0.0218(4) Uani 1 1 d . . . . .
H1M H 0.6038 0.8393 0.7680 0.042(12) Uiso 1 1 d R . . . .
C1M C 0.5781(5) 0.9980(3) 0.7299(3) 0.0293(7) Uani 1 1 d . . . . .
H1M1 H 0.6651 1.0482 0.6958 0.044 Uiso 1 1 calc R U . . .
H1M2 H 0.6246 1.0363 0.8122 0.044 Uiso 1 1 calc R U . . .
H1M3 H 0.4505 1.0002 0.6960 0.044 Uiso 1 1 calc R U . . .
O2M O 0.7080(3) 0.7820(2) 0.88392(17) 0.0231(4) Uani 1 1 d . . . . .
H2M H 0.6484 0.7014 0.8702 0.072(18) Uiso 1 1 d R . . . .
C2M C 0.9074(5) 0.8063(3) 0.9089(3) 0.0293(7) Uani 1 1 d . . . . .
H2M1 H 0.9816 0.8923 0.9619 0.044 Uiso 1 1 calc R U . . .
H2M2 H 0.9374 0.8042 0.8383 0.044 Uiso 1 1 calc R U . . .
H2M3 H 0.9398 0.7390 0.9435 0.044 Uiso 1 1 calc R U . . .
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'
O O 0.0106 0.0060 '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
O2 Cu N1 92.77(10) . . ?
O2 Cu O1M 89.32(10) . . ?
N1 Cu O1M 159.51(10) . . ?
O2 Cu O1 173.46(9) . . ?
N1 Cu O1 81.79(10) . . ?
O1M Cu O1 97.05(10) . . ?
O2 Cu O3 91.59(9) . . ?
N1 Cu O3 111.68(10) . . ?
O1M Cu O3 88.61(9) . . ?
O1 Cu O3 87.10(8) . . ?
C2 O2 Cu 126.3(2) . . ?
C2 C1 C3 120.0(3) . . ?
C2 C1 C7 123.1(3) . . ?
C3 C1 C7 116.9(3) . . ?
O2 C2 C1 125.2(3) . . ?
O2 C2 C6 117.5(3) . . ?
C1 C2 C6 117.3(3) . . ?
C4 C3 C1 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C1 C3 H3 119.6 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
O6 C6 C5 124.6(3) . . ?
O6 C6 C2 113.6(2) . . ?
C5 C6 C2 121.7(3) . . ?
C6 O6 C9 117.3(2) . . ?
N1 C7 C1 123.1(3) . . ?
N1 C7 H7 118.5 . . ?
C1 C7 H7 118.5 . . ?
C7 N1 N2 119.2(3) . . ?
C7 N1 Cu 128.2(2) . . ?
N2 N1 Cu 112.03(18) . . ?
C8 N2 N1 115.0(2) . . ?
C8 N2 H2 122.5 . . ?
N1 N2 H2 122.5 . . ?
O1 C8 N2 118.4(3) . . ?
O1 C8 C11 121.7(3) . . ?
N2 C8 C11 119.9(3) . . ?
C8 O1 Cu 112.77(18) . . ?
C21 C11 C61 118.0(3) . . ?
C21 C11 C8 123.0(3) . . ?
C61 C11 C8 118.9(3) . . ?
C31 C21 C11 121.1(3) . . ?
C31 C21 H21 119.5 . . ?
C11 C21 H21 119.5 . . ?
C21 C31 C41 120.8(3) . . ?
C21 C31 H31 119.6 . . ?
C41 C31 H31 119.6 . . ?
N3 C41 C51 121.2(3) . . ?
N3 C41 C31 120.4(3) . . ?
C51 C41 C31 118.3(3) . . ?
C61 C51 C41 120.3(3) . . ?
C61 C51 H51 119.9 . . ?
C41 C51 H51 119.9 . . ?
C51 C61 C11 121.4(3) . . ?
C51 C61 H61 119.3 . . ?
C11 C61 H61 119.3 . . ?
C41 N3 H3A 114.3 . . ?
C41 N3 H3B 125.4 . . ?
H3A N3 H3B 119.5 . . ?
O6 C9 H9A 109.5 . . ?
O6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 O3 Cu 120.66(17) . . ?
O5 N4 O4 120.3(3) . . ?
O5 N4 O3 120.0(2) . . ?
O4 N4 O3 119.7(3) . . ?
C1M O1M Cu 126.7(2) . . ?
C1M O1M H1M 114.5 . . ?
Cu O1M H1M 102.9 . . ?
O1M C1M H1M1 109.5 . . ?
O1M C1M H1M2 109.5 . . ?
H1M1 C1M H1M2 109.5 . . ?
O1M C1M H1M3 109.5 . . ?
H1M1 C1M H1M3 109.5 . . ?
H1M2 C1M H1M3 109.5 . . ?
C2M O2M H2M 109.5 . . ?
O2M C2M H2M1 109.5 . . ?
O2M C2M H2M2 109.5 . . ?
H2M1 C2M H2M2 109.5 . . ?
O2M C2M H2M3 109.5 . . ?
H2M1 C2M H2M3 109.5 . . ?
H2M2 C2M H2M3 109.5 . . ?
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
Cu O2 1.898(2) . ?
Cu N1 1.914(3) . ?
Cu O1M 1.958(3) . ?
Cu O1 1.966(2) . ?
Cu O3 2.375(2) . ?
O2 C2 1.324(3) . ?
C1 C2 1.411(4) . ?
C1 C3 1.422(4) . ?
C1 C7 1.432(4) . ?
C2 C6 1.424(4) . ?
C3 C4 1.372(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(4) . ?
C5 H5 0.9500 . ?
C6 O6 1.367(4) . ?
O6 C9 1.431(4) . ?
C7 N1 1.298(4) . ?
C7 H7 0.9500 . ?
N1 N2 1.378(4) . ?
N2 C8 1.350(4) . ?
N2 H2 0.8800 . ?
C8 O1 1.271(4) . ?
C8 C11 1.455(4) . ?
C11 C21 1.400(4) . ?
C11 C61 1.415(4) . ?
C21 C31 1.379(4) . ?
C21 H21 0.9500 . ?
C31 C41 1.414(4) . ?
C31 H31 0.9500 . ?
C41 N3 1.354(4) . ?
C41 C51 1.411(4) . ?
C51 C61 1.376(4) . ?
C51 H51 0.9500 . ?
C61 H61 0.9500 . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
O3 N4 1.270(3) . ?
N4 O5 1.241(4) . ?
N4 O4 1.254(3) . ?
O1M C1M 1.440(3) . ?
O1M H1M 0.8400 . ?
C1M H1M1 0.9800 . ?
C1M H1M2 0.9800 . ?
C1M H1M3 0.9800 . ?
O2M C2M 1.433(4) . ?
O2M H2M 0.8400 . ?
C2M H2M1 0.9800 . ?
C2M H2M2 0.9800 . ?
C2M H2M3 0.9800 . ?
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
C7 H7 O3 0.95 2.38 3.163(5) 139.2 2_566
N2 H2 O4 0.88 1.98 2.843(4) 166.5 2_566
N3 H3A O5 0.91 2.37 3.075(5) 134.4 1_454
N3 H3A O2M 0.91 2.35 3.109(4) 140.2 1_454
N3 H3B O5 0.91 2.22 3.100(3) 161.8 2_576
O1M H1M O2M 0.84 1.77 2.602(3) 170.1 .
O2M H2M O2 0.84 2.26 2.727(4) 115.5 .
O2M H2M O6 0.84 2.19 2.953(3) 151.1 .
