#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/04/7120443.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_7120443
loop_
_publ_author_name
'Rovira, Mireia'
'Jašíková, Lucie'
'Andris, Erik'
'Acuña-Pares, Ferran'
'Soler, Marta'
'Güell, Imma'
'Wang, Ming-Zheng'
'Gomez, Laura'
'Luis, Josep M.'
'Roithova, Jana'
'Ribas, Xavi'
_publ_section_title
;
 CuI/CuIII prototypical organometallic mechanism for the deactivation of
 an active pincer-like CuI catalyst in Ullmann-type couplings
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC04491G
_journal_year                    2017
_chemical_formula_moiety         'C9 H17 N3, 2(Cl) '
_chemical_formula_sum            'C9 H17 Cl2 N3'
_chemical_formula_weight         238.16
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-03-17 deposited with the CCDC.
2017-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.439(5)
_cell_length_b                   10.181(5)
_cell_length_c                   13.024(7)
_cell_measurement_reflns_used    4342
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      25.32
_cell_measurement_theta_min      2.94
_cell_volume                     1251.6(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20107
_diffrn_reflns_theta_full        28.52
_diffrn_reflns_theta_max         28.52
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.489
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.916763
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS v2.10 BRUKER 2001'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.163
_refine_diff_density_rms
'0.044 &#x00EF;&#x00BB;&#x00BF;#######################################################################'
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         3157
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0432P)²+0.1060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0903
_reflns_number_gt                2659
_reflns_number_total             3157
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc04491g2.cif
_cod_data_source_block           mwll1p37ev
_cod_original_cell_volume        1251.6(12)
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7120443
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.89490(5) 0.24528(5) 0.96202(4) 0.04626(14) Uani 1 1 d .
Cl2 Cl 0.92495(5) 0.73573(5) 0.85754(4) 0.04925(15) Uani 1 1 d .
N1 N 0.41057(18) 0.96490(16) 0.89338(13) 0.0397(4) Uani 1 1 d .
C1 C 0.5346(2) 0.90439(19) 0.88481(16) 0.0389(5) Uani 1 1 d .
N2 N 0.58340(18) 0.99612(17) 1.05454(13) 0.0390(4) Uani 1 1 d .
H2B H 0.520(2) 1.070(2) 1.0417(16) 0.047(6) Uiso 1 1 d .
H2C H 0.517(3) 0.919(3) 1.0846(19) 0.074(8) Uiso 1 1 d .
C2 C 0.5607(2) 0.8084(2) 0.81272(17) 0.0499(5) Uani 1 1 d .
H2A H 0.6517 0.7694 0.8067 0.060 Uiso 1 1 calc R
N3 N 0.1552(2) 1.06183(18) 0.94436(18) 0.0496(5) Uani 1 1 d .
H3C H 0.234(3) 1.112(3) 0.960(2) 0.073(9) Uiso 1 1 d .
H3B H 0.079(3) 1.126(2) 0.944(2) 0.073(8) Uiso 1 1 d .
C3 C 0.4513(3) 0.7709(3) 0.74990(19) 0.0622(7) Uani 1 1 d .
H3A H 0.4654 0.7043 0.6998 0.075 Uiso 1 1 calc R
C4 C 0.3210(3) 0.8301(3) 0.75970(18) 0.0549(6) Uani 1 1 d .
H4A H 0.2434 0.8041 0.7179 0.066 Uiso 1 1 calc R
C5 C 0.3062(2) 0.9276(2) 0.83145(16) 0.0415(5) Uani 1 1 d .
C6 C 0.6484(2) 0.9480(2) 0.95878(19) 0.0458(5) Uani 1 1 d .
H6A H 0.7122 0.8734 0.9742 0.055 Uiso 1 1 calc R
H6B H 0.7055 1.0189 0.9272 0.055 Uiso 1 1 calc R
C7 C 0.6876(3) 1.0325(3) 1.1345(2) 0.0560(6) Uani 1 1 d .
H7A H 0.6375 1.0624 1.1961 0.084 Uiso 1 1 calc R
H7B H 0.7484 1.1033 1.1089 0.084 Uiso 1 1 calc R
H7C H 0.7459 0.9559 1.1515 0.084 Uiso 1 1 calc R
C8 C 0.1699(2) 1.0027(2) 0.8413(2) 0.0507(6) Uani 1 1 d .
H8A H 0.1671 1.0729 0.7888 0.061 Uiso 1 1 calc R
H8B H 0.0892 0.9427 0.8285 0.061 Uiso 1 1 calc R
C9 C 0.1259(3) 0.9649(2) 1.0270(2) 0.0545(6) Uani 1 1 d .
H9A H 0.1179 1.0107 1.0929 0.082 Uiso 1 1 calc R
H9B H 0.2036 0.9012 1.0303 0.082 Uiso 1 1 calc R
H9C H 0.0370 0.9190 1.0121 0.082 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C5 118.05(18)
N1 C1 C2 123.0(2)
N1 C1 C6 115.92(19)
C2 C1 C6 121.10(19)
C6 N2 C7 113.71(17)
C6 N2 H2B 111.5(13)
C7 N2 H2B 109.6(13)
C6 N2 H2C 107.8(13)
C7 N2 H2C 108.1(14)
H2B N2 H2C 105.8(18)
C3 C2 C1 118.0(2)
C3 C2 H2A 121.0
C1 C2 H2A 121.0
C8 N3 C9 113.86(18)
C8 N3 H3C 110.3(17)
C9 N3 H3C 110.8(17)
C8 N3 H3B 109.8(16)
C9 N3 H3B 108.4(16)
H3C N3 H3B 103(2)
C2 C3 C4 119.7(2)
C2 C3 H3A 120.1
C4 C3 H3A 120.1
C5 C4 C3 118.1(2)
C5 C4 H4A 120.9
C3 C4 H4A 120.9
N1 C5 C4 123.1(2)
N1 C5 C8 116.0(2)
C4 C5 C8 120.9(2)
N2 C6 C1 109.98(17)
N2 C6 H6A 109.7
C1 C6 H6A 109.7
N2 C6 H6B 109.7
C1 C6 H6B 109.7
H6A C6 H6B 108.2
N2 C7 H7A 109.5
N2 C7 H7B 109.5
H7A C7 H7B 109.5
N2 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
N3 C8 C5 111.46(18)
N3 C8 H8A 109.3
C5 C8 H8A 109.3
N3 C8 H8B 109.3
C5 C8 H8B 109.3
H8A C8 H8B 108.0
N3 C9 H9A 109.5
N3 C9 H9B 109.5
H9A C9 H9B 109.5
N3 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.328(3)
N1 C5 1.329(3)
C1 C2 1.377(3)
C1 C6 1.510(3)
N2 C6 1.474(3)
N2 C7 1.480(3)
N2 H2B 0.98(2)
N2 H2C 1.08(3)
C2 C3 1.372(3)
C2 H2A 0.9500
N3 C8 1.478(3)
N3 C9 1.486(3)
N3 H3C 0.93(3)
N3 H3B 0.97(3)
C3 C4 1.376(4)
C3 H3A 0.9500
C4 C5 1.370(3)
C4 H4A 0.9500
C5 C8 1.502(3)
C6 H6A 0.9900
C6 H6B 0.9900
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 H8A 0.9900
C8 H8B 0.9900
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C5 N1 C1 C2 2.2(3)
C5 N1 C1 C6 -178.47(18)
N1 C1 C2 C3 -2.5(3)
C6 C1 C2 C3 178.2(2)
C1 C2 C3 C4 0.7(4)
C2 C3 C4 C5 1.4(4)
C1 N1 C5 C4 0.0(3)
C1 N1 C5 C8 -177.66(18)
C3 C4 C5 N1 -1.8(4)
C3 C4 C5 C8 175.8(2)
C7 N2 C6 C1 176.00(19)
N1 C1 C6 N2 28.6(3)
C2 C1 C6 N2 -152.01(19)
C9 N3 C8 C5 -71.9(2)
N1 C5 C8 N3 -25.0(3)
C4 C5 C8 N3 157.2(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139187901
