#------------------------------------------------------------------------------
#$Date: 2015-06-14 04:41:44 +0300 (Sun, 14 Jun 2015) $
#$Revision: 139182 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/99/2019975.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_2019975
loop_
_publ_author_name
'Bussey, Katherine A.'
'Cavalier, Annie R.'
'Connell, Jennifer R.'
'Mraz, Margaret E.'
'Oshin, Kayode D.'
'Pintauer, Tomislav'
'Oliver, Allen G.'
_publ_section_title
;
 Structural studies of (prop-2-en-1-yl)bis[(pyridin-2-yl)methylidene]amine
 hetero-scorpionate copper complexes
;
_journal_coeditor_code           SK3587
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229615010335
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          '[Cu Cl (C15 H17 N3)] Cl O4'
_chemical_formula_moiety         'C15 H17 Cl Cu N3 +, Cl O4 -'
_chemical_formula_sum            'C15 H17 Cl2 Cu N3 O4'
_chemical_formula_weight         437.76
_chemical_name_systematic
'Chlorido{(prop-2-en-1-yl)bis[pyridin-2-yl)methylidene]amine-κ³N,N',N''}copper(II) perchlorate'
_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'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 101.677(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4260(12)
_cell_length_b                   14.832(2)
_cell_length_c                   14.007(2)
_cell_measurement_reflns_used    4302
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.0675
_cell_measurement_theta_min      2.736
_cell_volume                     1714.3(4)
_computing_cell_refinement
;
SAINT (Bruker, 2008)
;
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_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 0.948
_diffrn_measurement_device_type  'Bruker SMART 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  0.0534
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10763
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.561
_diffrn_reflns_theta_min         2.747
_exptl_absorpt_coefficient_mu    1.612
_exptl_absorpt_correction_T_max  0.8814
_exptl_absorpt_correction_T_min  0.6200
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_description       rhomboid
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.934
_refine_diff_density_min         -0.644
_refine_ls_abs_structure_details
;
Flack x determined using 1902 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack   -0.005(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         5553
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0397
_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)+(0.0510P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                4766
_reflns_number_total             5553
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3587sup1.cif
_cod_data_source_block           4
_cod_database_code               2019975
_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   0.686
_shelx_estimated_absorpt_t_max   0.907
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_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 0.66284(4) 0.72310(3) 0.72527(3) 0.02040(12) Uani d 1
Cl Cl1 0.76060(14) 0.58664(7) 0.76668(9) 0.0313(2) Uani d 1
N N1 0.4650(4) 0.7138(2) 0.7820(3) 0.0226(7) Uani d 1
N N2 0.5842(4) 0.8531(2) 0.6986(2) 0.0186(6) Uani d 1
N N3 0.8353(4) 0.7649(2) 0.6587(2) 0.0216(7) Uani d 1
C C1 0.3905(6) 0.6378(3) 0.7988(3) 0.0290(9) Uani d 1
H H1 0.4400 0.5815 0.7908 0.035 Uiso calc 1
C C2 0.2443(6) 0.6391(4) 0.8275(4) 0.0332(10) Uani d 1
H H2 0.1925 0.5842 0.8381 0.040 Uiso calc 1
C C3 0.1725(6) 0.7206(3) 0.8411(3) 0.0315(10) Uani d 1
H H3 0.0716 0.7224 0.8615 0.038 Uiso calc 1
C C4 0.2505(5) 0.8002(3) 0.8244(3) 0.0278(9) Uani d 1
H H4 0.2042 0.8572 0.8330 0.033 Uiso calc 1
C C5 0.3970(5) 0.7939(3) 0.7948(3) 0.0228(8) Uani d 1
C C6 0.4969(5) 0.8748(3) 0.7773(3) 0.0223(8) Uani d 1
H H6A 0.4253 0.9275 0.7584 0.027 Uiso calc 1
H H6B 0.5755 0.8901 0.8378 0.027 Uiso calc 1
C C7 0.7305(5) 0.9084(3) 0.6999(3) 0.0229(8) Uani d 1
H H7A 0.7859 0.9209 0.7679 0.027 Uiso calc 1
H H7B 0.7006 0.9665 0.6664 0.027 Uiso calc 1
C C8 0.8414(5) 0.8552(3) 0.6475(3) 0.0225(8) Uani d 1
C C9 0.9431(6) 0.8942(4) 0.5936(4) 0.0326(10) Uani d 1
H H9 0.9477 0.9579 0.5878 0.039 Uiso calc 1
C C10 1.0386(6) 0.8394(4) 0.5482(4) 0.0377(12) Uani d 1
H H10 1.1074 0.8650 0.5094 0.045 Uiso calc 1
C C11 1.0321(6) 0.7478(4) 0.5600(4) 0.0355(11) Uani d 1
H H11 1.0970 0.7091 0.5297 0.043 Uiso calc 1
C C12 0.9305(5) 0.7127(3) 0.6163(3) 0.0289(9) Uani d 1
H H12 0.9280 0.6492 0.6252 0.035 Uiso calc 1
C C13 0.4719(5) 0.8569(3) 0.6009(3) 0.0227(8) Uani d 1
H H13A 0.5310 0.8357 0.5508 0.027 Uiso calc 1
H H13B 0.3810 0.8146 0.6011 0.027 Uiso calc 1
C C14 0.4033(6) 0.9487(3) 0.5723(3) 0.0273(9) Uani d 1
H H14 0.3364 0.9763 0.6110 0.033 Uiso calc 1
C C15 0.4322(7) 0.9929(4) 0.4953(3) 0.0401(12) Uani d 1
H H15A 0.4988 0.9666 0.4557 0.048 Uiso calc 1
H H15B 0.3864 1.0509 0.4798 0.048 Uiso calc 1
Cl Cl2 0.41399(12) 0.63022(7) 0.47752(8) 0.0252(2) Uani d 1
O O1 0.4560(8) 0.5597(4) 0.4223(3) 0.0767(18) Uani d 1
O O2 0.3144(10) 0.6004(6) 0.5373(8) 0.171(5) Uani d 1
O O3 0.5608(8) 0.6629(4) 0.5360(5) 0.107(3) Uani d 1
O O4 0.3369(4) 0.7032(2) 0.4174(3) 0.0319(7) Uani d 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'
O O 0.0106 0.0060 '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_publ_flag
N3 Cu1 N1 164.53(15) y
N3 Cu1 N2 81.96(14) y
N1 Cu1 N2 82.65(14) y
N3 Cu1 Cl1 98.06(11) y
N1 Cu1 Cl1 97.42(11) y
N2 Cu1 Cl1 174.94(10) y
C1 N1 C5 119.6(4) ?
C1 N1 Cu1 126.2(3) ?
C5 N1 Cu1 113.9(3) ?
C6 N2 C7 114.1(3) ?
C6 N2 C13 110.8(3) ?
C7 N2 C13 111.2(3) ?
C6 N2 Cu1 105.1(2) ?
C7 N2 Cu1 106.3(2) ?
C13 N2 Cu1 108.9(2) ?
C12 N3 C8 118.9(4) ?
C12 N3 Cu1 126.2(3) ?
C8 N3 Cu1 114.5(3) ?
N1 C1 C2 121.5(4) ?
N1 C1 H1 119.2 ?
C2 C1 H1 119.2 ?
C1 C2 C3 119.8(5) ?
C1 C2 H2 120.1 ?
C3 C2 H2 120.1 ?
C2 C3 C4 118.9(4) ?
C2 C3 H3 120.6 ?
C4 C3 H3 120.6 ?
C5 C4 C3 118.3(4) ?
C5 C4 H4 120.9 ?
C3 C4 H4 120.9 ?
N1 C5 C4 122.0(4) ?
N1 C5 C6 114.4(4) ?
C4 C5 C6 123.6(4) ?
N2 C6 C5 108.9(3) ?
N2 C6 H6A 109.9 ?
C5 C6 H6A 109.9 ?
N2 C6 H6B 109.9 ?
C5 C6 H6B 109.9 ?
H6A C6 H6B 108.3 ?
N2 C7 C8 107.4(3) ?
N2 C7 H7A 110.2 ?
C8 C7 H7A 110.2 ?
N2 C7 H7B 110.2 ?
C8 C7 H7B 110.2 ?
H7A C7 H7B 108.5 ?
N3 C8 C9 121.5(4) ?
N3 C8 C7 114.7(4) ?
C9 C8 C7 123.8(4) ?
C8 C9 C10 119.2(5) ?
C8 C9 H9 120.4 ?
C10 C9 H9 120.4 ?
C11 C10 C9 119.0(5) ?
C11 C10 H10 120.5 ?
C9 C10 H10 120.5 ?
C10 C11 C12 119.2(5) ?
C10 C11 H11 120.4 ?
C12 C11 H11 120.4 ?
N3 C12 C11 122.2(5) ?
N3 C12 H12 118.9 ?
C11 C12 H12 118.9 ?
C14 C13 N2 114.5(3) ?
C14 C13 H13A 108.6 ?
N2 C13 H13A 108.6 ?
C14 C13 H13B 108.6 ?
N2 C13 H13B 108.6 ?
H13A C13 H13B 107.6 ?
C15 C14 C13 122.8(5) ?
C15 C14 H14 118.6 ?
C13 C14 H14 118.6 ?
C14 C15 H15A 120.0 ?
C14 C15 H15B 120.0 ?
H15A C15 H15B 120.0 ?
O2 Cl2 O1 110.6(5) ?
O2 Cl2 O3 109.1(7) ?
O1 Cl2 O3 106.7(4) ?
O2 Cl2 O4 109.8(3) ?
O1 Cl2 O4 112.1(3) ?
O3 Cl2 O4 108.5(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 N3 1.979(4) y
Cu1 N1 1.991(4) y
Cu1 N2 2.048(3) y
Cu1 Cl1 2.2176(11) y
N1 C1 1.333(6) ?
N1 C5 1.346(5) ?
N2 C6 1.480(5) ?
N2 C7 1.478(5) ?
N2 C13 1.498(5) ?
N3 C12 1.338(6) ?
N3 C8 1.350(6) ?
C1 C2 1.372(7) ?
C1 H1 0.9500 ?
C2 C3 1.382(7) ?
C2 H2 0.9500 ?
C3 C4 1.393(7) ?
C3 H3 0.9500 ?
C4 C5 1.382(6) ?
C4 H4 0.9500 ?
C5 C6 1.515(6) ?
C6 H6A 0.9900 ?
C6 H6B 0.9900 ?
C7 C8 1.520(6) ?
C7 H7A 0.9900 ?
C7 H7B 0.9900 ?
C8 C9 1.379(6) ?
C9 C10 1.386(8) ?
C9 H9 0.9500 ?
C10 C11 1.371(9) ?
C10 H10 0.9500 ?
C11 C12 1.379(7) ?
C11 H11 0.9500 ?
C12 H12 0.9500 ?
C13 C14 1.502(6) ?
C13 H13A 0.9900 ?
C13 H13B 0.9900 ?
C14 C15 1.326(7) ?
C14 H14 0.9500 ?
C15 H15A 0.9500 ?
C15 H15B 0.9500 ?
Cl2 O2 1.372(6) ?
Cl2 O1 1.388(5) ?
Cl2 O3 1.423(5) ?
Cl2 O4 1.443(3) ?
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 1.1(7)
Cu1 N1 C1 C2 -172.3(4)
N1 C1 C2 C3 -1.1(8)
C1 C2 C3 C4 0.5(7)
C2 C3 C4 C5 0.0(7)
C1 N1 C5 C4 -0.6(6)
Cu1 N1 C5 C4 173.6(3)
C1 N1 C5 C6 177.6(4)
Cu1 N1 C5 C6 -8.2(4)
C3 C4 C5 N1 0.1(6)
C3 C4 C5 C6 -178.0(4)
C7 N2 C6 C5 -157.0(3)
C13 N2 C6 C5 76.5(4)
Cu1 N2 C6 C5 -40.9(3)
N1 C5 C6 N2 34.0(5)
C4 C5 C6 N2 -147.9(4)
C6 N2 C7 C8 156.3(3)
C13 N2 C7 C8 -77.5(4)
Cu1 N2 C7 C8 40.9(3)
C12 N3 C8 C9 0.0(6)
Cu1 N3 C8 C9 -173.1(3)
C12 N3 C8 C7 -179.1(4)
Cu1 N3 C8 C7 7.9(4)
N2 C7 C8 N3 -33.3(4)
N2 C7 C8 C9 147.6(4)
N3 C8 C9 C10 1.4(6)
C7 C8 C9 C10 -179.6(4)
C8 C9 C10 C11 -1.6(7)
C9 C10 C11 C12 0.3(7)
C8 N3 C12 C11 -1.3(6)
Cu1 N3 C12 C11 170.8(3)
C10 C11 C12 N3 1.2(7)
C6 N2 C13 C14 64.3(5)
C7 N2 C13 C14 -63.7(5)
Cu1 N2 C13 C14 179.4(3)
N2 C13 C14 C15 117.2(5)

_cod_database_fobs_code 2019975
