#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/04/2240456.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2240456
loop_
_publ_author_name
'Bussey, Katherine A.'
'Connell, Jennifer R.'
'McGlone, Annie R.'
'Mraz, Margaret E.'
'Oshin, Kayode D.'
'Pintauer, Tomislav'
'Oliver, Allen G.'
_publ_section_title
;
 Crystal structure of
 {(but-3-en-1-yl)bis[(pyridin-2-yl)methyl]amine-κ³N,N',N''}dichloridocopper(II)
 diethyl ether hemisolvate
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              309
_journal_page_last               311
_journal_paper_doi               10.1107/S2056989015003448
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          '[Cu Cl2 (C16 H19 N3)], 0.5C4 H10 O'
_chemical_formula_moiety         'C16 H19 Cl2 Cu N3, 0.5(C4 H10 O)'
_chemical_formula_sum            'C18 H24 Cl2 Cu N3 O0.5'
_chemical_formula_weight         424.84
_chemical_name_systematic
;{(But-3-en-1-yl)bis[(pyridin-2-yl)methyl]amine-κ³N,N',N''} dichloridocopper(II)
diethyl ether hemisolvate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 108.7710(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.1614(13)
_cell_length_b                   11.5738(5)
_cell_length_c                   16.4530(7)
_cell_measurement_reflns_used    8841
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.22
_cell_measurement_theta_min      2.22
_cell_volume                     3995.6(3)
_computing_cell_refinement
;
SAINT (Bruker, 2010)
;
_computing_data_collection
;
APEX2 (Bruker, 2010)
;
_computing_data_reduction
;
SAINT (Bruker, 2010)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2006) and POV-Ray (Cason, 2013)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'φ and ω 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  0.0254
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            24823
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.606
_diffrn_reflns_theta_min         1.941
_exptl_absorpt_coefficient_mu    1.368
_exptl_absorpt_correction_T_max  0.8396
_exptl_absorpt_correction_T_min  0.4705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       rhomboid
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.276
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.431
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         6872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0276
_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)+(0.0348P)²+2.0749P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0667
_refine_ls_wR_factor_ref         0.0721
_reflns_number_gt                5660
_reflns_number_total             6872
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pk2546sup1.cf
_cod_data_source_block           I
_cod_original_formula_sum        'C18 H24 Cl2 Cu1 N3 O0.5'
_cod_database_code               2240456
_cod_database_fobs_code          2240456
#BEGIN Tags that were not found in dictionaries:
_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   0.548
_shelx_estimated_absorpt_t_max   0.873
#END Tags that were not found in dictionaries
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'
'-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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
Cu Cu1 0.15616(2) 0.59899(2) 0.13662(2) 0.01989(5) Uani d 1
Cl Cl1 0.09795(2) 0.43892(3) 0.13435(2) 0.03418(8) Uani d 1
Cl Cl2 0.25976(2) 0.52731(3) 0.12375(2) 0.02394(7) Uani d 1
N N1 0.18137(5) 0.77181(9) 0.14348(6) 0.01978(19) Uani d 1
N N2 0.11788(5) 0.64014(9) 0.01190(7) 0.0215(2) Uani d 1
N N3 0.19179(5) 0.61566(9) 0.26406(7) 0.0223(2) Uani d 1
C C1 0.19332(6) 0.79568(11) 0.06162(8) 0.0219(2) Uani d 1
H H1A 0.2363 0.7679 0.0650 0.026 Uiso calc 1
H H1B 0.1915 0.8800 0.0508 0.026 Uiso calc 1
C C2 0.14371(6) 0.73526(11) -0.01065(8) 0.0205(2) Uani d 1
C C3 0.12747(6) 0.77160(12) -0.09536(8) 0.0240(2) Uani d 1
H H3 0.1460 0.8393 -0.1099 0.029 Uiso calc 1
C C4 0.08364(6) 0.70725(13) -0.15849(8) 0.0275(3) Uani d 1
H H4 0.0728 0.7289 -0.2171 0.033 Uiso calc 1
C C5 0.05600(7) 0.61125(13) -0.13490(9) 0.0287(3) Uani d 1
H H5 0.0251 0.5674 -0.1770 0.034 Uiso calc 1
C C6 0.07399(6) 0.57991(12) -0.04920(9) 0.0263(3) Uani d 1
H H6 0.0549 0.5141 -0.0331 0.032 Uiso calc 1
C C7 0.23897(6) 0.78269(11) 0.22018(8) 0.0223(2) Uani d 1
H H7A 0.2440 0.8638 0.2403 0.027 Uiso calc 1
H H7B 0.2773 0.7607 0.2053 0.027 Uiso calc 1
C C8 0.23224(6) 0.70480(11) 0.29021(8) 0.0219(2) Uani d 1
C C9 0.26692(7) 0.72191(12) 0.37617(9) 0.0284(3) Uani d 1
H H9 0.2956 0.7850 0.3935 0.034 Uiso calc 1
C C10 0.25854(8) 0.64431(13) 0.43618(9) 0.0315(3) Uani d 1
H H10 0.2825 0.6525 0.4952 0.038 Uiso calc 1
C C11 0.21516(7) 0.55514(13) 0.40935(9) 0.0298(3) Uani d 1
H H11 0.2076 0.5034 0.4499 0.036 Uiso calc 1
C C12 0.18308(7) 0.54244(12) 0.32283(9) 0.0263(3) Uani d 1
H H12 0.1540 0.4802 0.3042 0.032 Uiso calc 1
C C13 0.12613(6) 0.83899(11) 0.15197(9) 0.0250(2) Uani d 1
H H13A 0.1182 0.8139 0.2052 0.030 Uiso calc 1
H H13B 0.0879 0.8187 0.1031 0.030 Uiso calc 1
C C14 0.13334(8) 0.97031(13) 0.15463(11) 0.0370(3) Uani d 1
H H14A 0.1719 0.9922 0.2024 0.044 Uiso calc 1
H H14B 0.1387 0.9976 0.1003 0.044 Uiso calc 1
C C15 0.07651(10) 1.02672(16) 0.16678(14) 0.0517(5) Uani d 1
H H15 0.0648 1.0031 0.2150 0.062 Uiso calc 1
C C16 0.04196(14) 1.1043(2) 0.1180(2) 0.0866(9) Uani d 1
H H16A 0.0519 1.1306 0.0691 0.104 Uiso calc 1
H H16B 0.0064 1.1356 0.1308 0.104 Uiso calc 1
O O1 0.5000 0.71720(17) 0.7500 0.0552(5) Uani d 1
C C17 0.46509(12) 0.7851(2) 0.6791(2) 0.0809(9) Uani d 1
H H17A 0.4948 0.8292 0.6570 0.097 Uiso calc 1
H H17B 0.4381 0.8409 0.6973 0.097 Uiso calc 1
C C18 0.42468(16) 0.7095(4) 0.6110(2) 0.1069(12) Uani d 1
H H18A 0.4016 0.7564 0.5610 0.160 Uiso calc 1
H H18B 0.3941 0.6687 0.6323 0.160 Uiso calc 1
H H18C 0.4515 0.6531 0.5942 0.160 Uiso calc 1
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'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle
N3 Cu1 N2 . 160.62(5)
N3 Cu1 N1 . 80.84(4)
N2 Cu1 N1 . 81.05(4)
N3 Cu1 Cl1 . 97.34(3)
N2 Cu1 Cl1 . 97.28(3)
N1 Cu1 Cl1 . 159.94(3)
N3 Cu1 Cl2 . 93.27(3)
N2 Cu1 Cl2 . 95.11(3)
N1 Cu1 Cl2 . 94.92(3)
Cl1 Cu1 Cl2 . 105.136(14)
C1 N1 C7 . 113.65(9)
C1 N1 C13 . 112.33(10)
C7 N1 C13 . 112.52(10)
C1 N1 Cu1 . 104.77(7)
C7 N1 Cu1 . 105.76(7)
C13 N1 Cu1 . 107.05(8)
C6 N2 C2 . 119.11(11)
C6 N2 Cu1 . 127.29(9)
C2 N2 Cu1 . 113.44(8)
C8 N3 C12 . 119.27(11)
C8 N3 Cu1 . 114.07(8)
C12 N3 Cu1 . 126.42(9)
N1 C1 C2 . 109.43(10)
N1 C1 H1A . 109.8
C2 C1 H1A . 109.8
N1 C1 H1B . 109.8
C2 C1 H1B . 109.8
H1A C1 H1B . 108.2
N2 C2 C3 . 121.90(12)
N2 C2 C1 . 115.39(10)
C3 C2 C1 . 122.65(11)
C2 C3 C4 . 118.80(12)
C2 C3 H3 . 120.6
C4 C3 H3 . 120.6
C5 C4 C3 . 119.17(12)
C5 C4 H4 . 120.4
C3 C4 H4 . 120.4
C4 C5 C6 . 119.20(13)
C4 C5 H5 . 120.4
C6 C5 H5 . 120.4
N2 C6 C5 . 121.79(13)
N2 C6 H6 . 119.1
C5 C6 H6 . 119.1
N1 C7 C8 . 109.24(10)
N1 C7 H7A . 109.8
C8 C7 H7A . 109.8
N1 C7 H7B . 109.8
C8 C7 H7B . 109.8
H7A C7 H7B . 108.3
N3 C8 C9 . 121.93(12)
N3 C8 C7 . 115.75(11)
C9 C8 C7 . 122.30(12)
C8 C9 C10 . 118.31(13)
C8 C9 H9 . 120.8
C10 C9 H9 . 120.8
C11 C10 C9 . 119.57(13)
C11 C10 H10 . 120.2
C9 C10 H10 . 120.2
C12 C11 C10 . 118.92(13)
C12 C11 H11 . 120.5
C10 C11 H11 . 120.5
N3 C12 C11 . 121.94(13)
N3 C12 H12 . 119.0
C11 C12 H12 . 119.0
N1 C13 C14 . 116.05(11)
N1 C13 H13A . 108.3
C14 C13 H13A . 108.3
N1 C13 H13B . 108.3
C14 C13 H13B . 108.3
H13A C13 H13B . 107.4
C15 C14 C13 . 110.80(14)
C15 C14 H14A . 109.5
C13 C14 H14A . 109.5
C15 C14 H14B . 109.5
C13 C14 H14B . 109.5
H14A C14 H14B . 108.1
C16 C15 C14 . 125.8(2)
C16 C15 H15 . 117.1
C14 C15 H15 . 117.1
C15 C16 H16A . 120.0
C15 C16 H16B . 120.0
H16A C16 H16B . 120.0
C17 O1 C17 2_656 112.4(3)
O1 C17 C18 . 109.5(2)
O1 C17 H17A . 109.8
C18 C17 H17A . 109.8
O1 C17 H17B . 109.8
C18 C17 H17B . 109.8
H17A C17 H17B . 108.2
C17 C18 H18A . 109.5
C17 C18 H18B . 109.5
H18A C18 H18B . 109.5
C17 C18 H18C . 109.5
H18A C18 H18C . 109.5
H18B C18 H18C . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cu1 N3 . 1.9980(11)
Cu1 N2 . 2.0093(11)
Cu1 N1 . 2.0700(10)
Cu1 Cl1 . 2.2508(4)
Cu1 Cl2 . 2.5134(4)
N1 C1 . 1.4800(15)
N1 C7 . 1.4837(16)
N1 C13 . 1.4942(16)
N2 C6 . 1.3466(16)
N2 C2 . 1.3469(16)
N3 C8 . 1.3434(17)
N3 C12 . 1.3455(16)
C1 C2 . 1.5067(17)
C1 H1A . 0.9900
C1 H1B . 0.9900
C2 C3 . 1.3878(17)
C3 C4 . 1.3883(19)
C3 H3 . 0.9500
C4 C5 . 1.383(2)
C4 H4 . 0.9500
C5 C6 . 1.3845(19)
C5 H5 . 0.9500
C6 H6 . 0.9500
C7 C8 . 1.5077(17)
C7 H7A . 0.9900
C7 H7B . 0.9900
C8 C9 . 1.3895(18)
C9 C10 . 1.391(2)
C9 H9 . 0.9500
C10 C11 . 1.383(2)
C10 H10 . 0.9500
C11 C12 . 1.379(2)
C11 H11 . 0.9500
C12 H12 . 0.9500
C13 C14 . 1.527(2)
C13 H13A . 0.9900
C13 H13B . 0.9900
C14 C15 . 1.488(2)
C14 H14A . 0.9900
C14 H14B . 0.9900
C15 C16 . 1.281(3)
C15 H15 . 0.9500
C16 H16A . 0.9500
C16 H16B . 0.9500
O1 C17 2_656 1.413(3)
O1 C17 . 1.413(3)
C17 C18 . 1.476(4)
C17 H17A . 0.9900
C17 H17B . 0.9900
C18 H18A . 0.9800
C18 H18B . 0.9800
C18 H18C . 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C3 H3 Cl2 7_565 0.95 2.67 3.5541(15) 156
C11 H11 Cl2 6_566 0.95 2.74 3.4767(15) 135
C14 H14A Cl2 4 0.99 2.80 3.7127(18) 153
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_site_symmetry_1
_geom_torsion
C7 N1 C1 C2 . 155.62(10)
C13 N1 C1 C2 . -75.20(13)
Cu1 N1 C1 C2 . 40.65(11)
C6 N2 C2 C3 . -1.47(18)
Cu1 N2 C2 C3 . 174.32(10)
C6 N2 C2 C1 . -178.80(11)
Cu1 N2 C2 C1 . -3.00(13)
N1 C1 C2 N2 . -26.50(15)
N1 C1 C2 C3 . 156.20(11)
N2 C2 C3 C4 . -0.47(19)
C1 C2 C3 C4 . 176.66(12)
C2 C3 C4 C5 . 2.0(2)
C3 C4 C5 C6 . -1.7(2)
C2 N2 C6 C5 . 1.8(2)
Cu1 N2 C6 C5 . -173.32(10)
C4 C5 C6 N2 . -0.2(2)
C1 N1 C7 C8 . -152.29(10)
C13 N1 C7 C8 . 78.63(12)
Cu1 N1 C7 C8 . -37.91(11)
C12 N3 C8 C9 . 1.93(19)
Cu1 N3 C8 C9 . -172.73(10)
C12 N3 C8 C7 . -179.82(11)
Cu1 N3 C8 C7 . 5.52(14)
N1 C7 C8 N3 . 22.88(15)
N1 C7 C8 C9 . -158.88(12)
N3 C8 C9 C10 . -0.6(2)
C7 C8 C9 C10 . -178.72(12)
C8 C9 C10 C11 . -1.8(2)
C9 C10 C11 C12 . 2.7(2)
C8 N3 C12 C11 . -0.91(19)
Cu1 N3 C12 C11 . 173.03(10)
C10 C11 C12 N3 . -1.4(2)
C1 N1 C13 C14 . -63.24(15)
C7 N1 C13 C14 . 66.53(14)
Cu1 N1 C13 C14 . -177.71(10)
N1 C13 C14 C15 . -177.66(13)
C13 C14 C15 C16 . -125.1(3)
C17 O1 C17 C18 2_656 -174.1(3)
