#------------------------------------------------------------------------------
#$Date: 2018-04-30 18:49:40 +0300 (Mon, 30 Apr 2018) $
#$Revision: 207528 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/10/2021089.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_2021089
loop_
_publ_author_name
'Potočňák, Ivan'
'Bukrynov, Oleksandr'
'Kliuikov, Andrii'
'Čižmár, Erik'
'Vitushkina, Svitlana'
'Váhovská, Lucia'
'Dušek, Michal'
_publ_section_title
;
 A CuII complex with an carbamoylcyanonitrosomethanide ligand formed
 in situ by the nucleophilic addition of water to
 dicyanonitrosomethanide: structure, spectral and magnetic properties
;
_journal_coeditor_code           SK3686
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              584
_journal_page_last               589
_journal_paper_doi               10.1107/S2053229618005697
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          '[Cu (C3 H2 N3 O2) Cl (C18 H12 N2)], C2 H3 N'
_chemical_formula_moiety         'C21 H14 Cl Cu N5 O2, C2 H3 N'
_chemical_formula_sum            'C23 H17 Cl N6 O2'
_chemical_formula_weight         508.42
_chemical_name_systematic
;
(2,2'-Biquinoline-κ²N,N')(carbamoylcyanonitrosomethanide-\
κ²N,O)chloridocopper(II) acetonitrile monosolvate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.4680(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.82030(10)
_cell_length_b                   9.12760(10)
_cell_length_c                   21.15750(10)
_cell_measurement_reflns_used    21847
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      67.6560
_cell_measurement_theta_min      4.2330
_cell_volume                     2244.71(3)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2017)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2017)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2017)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b) in WinGX (Farrugia, 2012)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 5.1783
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Xcalibur AtlasS2 Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            40629
_diffrn_reflns_theta_full        67.586
_diffrn_reflns_theta_max         67.586
_diffrn_reflns_theta_min         3.803
_exptl_absorpt_coefficient_mu    2.750
_exptl_absorpt_correction_T_max  0.927
_exptl_absorpt_correction_T_min  0.593
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
[CrysAlis PRO (Rigaku OD, 2017), based on expressions
derived by Clark & Reid (1995)]
;
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_description       plate
_exptl_crystal_F_000             1036
_exptl_crystal_size_max          0.306
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.295
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0237
_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)+(0.0332P)²+1.4117P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0656
_reflns_number_gt                3765
_reflns_number_total             4034
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sk3686sup1.cif
_cod_data_source_block           I
_cod_database_code               2021089
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.84543(2) 0.67370(2) 0.62482(2) 0.01704(8) Uani d 1
Cl Cl1 0.98942(3) 0.52820(4) 0.67748(2) 0.02252(10) Uani d 1
O O2 0.74668(9) 0.61544(13) 0.68669(5) 0.0218(2) Uani d 1
O O1 0.74223(10) 0.96188(13) 0.58230(5) 0.0254(3) Uani d 1
N N20 0.94414(10) 0.75413(14) 0.56619(6) 0.0168(3) Uani d 1
N N10 0.77747(11) 0.55355(14) 0.53480(6) 0.0180(3) Uani d 1
N N1 0.74096(11) 0.85218(15) 0.61833(6) 0.0183(3) Uani d 1
N N2 0.59380(13) 0.67900(19) 0.73050(7) 0.0266(3) Uani d 1
N N3 0.51050(12) 1.04133(16) 0.66124(7) 0.0286(3) Uani d 1
C C21 0.93414(13) 0.69337(17) 0.50823(7) 0.0175(3) Uani d 1
C C22 1.02823(13) 0.85627(17) 0.58589(7) 0.0175(3) Uani d 1
C C27 1.10787(13) 0.89555(18) 0.54590(7) 0.0190(3) Uani d 1
N N4 0.37291(14) 0.82051(19) 0.74661(9) 0.0387(4) Uani d 1
C C1 0.66365(13) 0.84313(18) 0.65695(7) 0.0185(3) Uani d 1
C C12 0.69170(13) 0.45126(18) 0.52100(8) 0.0204(3) Uani d 1
C C11 0.83902(13) 0.58648(17) 0.48996(7) 0.0185(3) Uani d 1
C C2 0.66930(13) 0.70659(18) 0.69295(7) 0.0199(3) Uani d 1
C C17 0.66875(14) 0.37865(19) 0.46055(8) 0.0243(3) Uani d 1
C C29 1.01142(13) 0.72761(18) 0.46644(7) 0.0204(3) Uani d 1
H H29 1.0036 0.6819 0.4255 0.024 Uiso calc 1
C C3 0.58020(13) 0.95479(18) 0.65906(7) 0.0209(3) Uani d 1
C C28 1.09693(13) 0.82663(18) 0.48539(8) 0.0207(3) Uani d 1
H H28 1.1495 0.8494 0.4578 0.025 Uiso calc 1
C C23 1.03632(13) 0.92393(19) 0.64663(7) 0.0216(3) Uani d 1
H H23 0.9838 0.8980 0.6739 0.026 Uiso calc 1
C C26 1.19398(13) 1.00064(19) 0.56815(8) 0.0225(3) Uani d 1
H H26 1.2482 1.0268 0.5420 0.027 Uiso calc 1
C C24 1.11937(14) 1.0264(2) 0.66624(8) 0.0253(4) Uani d 1
H H24 1.1234 1.0726 0.7068 0.030 Uiso calc 1
C C19 0.81741(14) 0.5229(2) 0.42781(8) 0.0251(4) Uani d 1
H H19 0.8607 0.5522 0.3963 0.030 Uiso calc 1
C C25 1.19955(14) 1.0645(2) 0.62684(8) 0.0256(4) Uani d 1
H H25 1.2576 1.1350 0.6414 0.031 Uiso calc 1
C C13 0.62539(14) 0.41411(19) 0.56798(8) 0.0250(4) Uani d 1
H H13 0.6387 0.4627 0.6083 0.030 Uiso calc 1
C C4 0.29640(15) 0.7813(2) 0.76818(8) 0.0276(4) Uani d 1
C C5 0.19909(16) 0.7316(2) 0.79585(10) 0.0299(4) Uani d 1
C C18 0.73392(15) 0.4194(2) 0.41403(8) 0.0279(4) Uani d 1
H H18 0.7196 0.3745 0.3728 0.033 Uiso calc 1
C C16 0.58372(15) 0.2677(2) 0.45003(9) 0.0311(4) Uani d 1
H H16 0.5697 0.2168 0.4102 0.037 Uiso calc 1
C C14 0.54218(15) 0.3085(2) 0.55557(9) 0.0307(4) Uani d 1
H H14 0.4975 0.2854 0.5873 0.037 Uiso calc 1
C C15 0.52189(15) 0.2332(2) 0.49628(10) 0.0333(4) Uani d 1
H H15 0.4651 0.1585 0.4887 0.040 Uiso calc 1
H H2N2 0.5987(17) 0.600(3) 0.7498(10) 0.027(5) Uiso d 1
H H1N2 0.5418(19) 0.736(3) 0.7336(10) 0.034(6) Uiso d 1
H H1C5 0.2262(19) 0.673(3) 0.8336(11) 0.042(6) Uiso d 1
H H3C5 0.154(2) 0.816(3) 0.8048(11) 0.046(6) Uiso d 1
H H2C5 0.149(2) 0.667(3) 0.7654(12) 0.047(7) Uiso 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
O2 Cu1 N20 173.84(5) y
O2 Cu1 N1 80.56(5) y
N20 Cu1 N1 94.59(5) y
O2 Cu1 N10 105.67(5) y
N20 Cu1 N10 79.00(5) y
N1 Cu1 N10 102.55(5) y
O2 Cu1 Cl1 89.88(3) y
N20 Cu1 Cl1 92.82(4) y
N1 Cu1 Cl1 152.69(4) y
N10 Cu1 Cl1 104.66(4) y
C2 O2 Cu1 114.74(10) ?
C21 N20 C22 120.09(13) ?
C21 N20 Cu1 117.14(11) ?
C22 N20 Cu1 122.39(10) ?
C11 N10 C12 118.77(13) ?
C11 N10 Cu1 109.93(10) ?
C12 N10 Cu1 131.18(10) ?
O1 N1 C1 120.28(13) y
O1 N1 Cu1 127.12(10) ?
C1 N1 Cu1 112.58(10) ?
C2 N2 H2N2 118.1(14) ?
C2 N2 H1N2 121.6(15) ?
H2N2 N2 H1N2 120(2) ?
N20 C21 C29 121.57(15) ?
N20 C21 C11 116.71(13) ?
C29 C21 C11 121.72(14) ?
N20 C22 C23 119.94(13) ?
N20 C22 C27 120.83(14) ?
C23 C22 C27 119.23(14) ?
C28 C27 C26 123.07(14) ?
C28 C27 C22 117.79(15) ?
C26 C27 C22 119.14(14) ?
N1 C1 C3 122.00(14) y
N1 C1 C2 113.70(14) y
C3 C1 C2 124.21(14) y
N10 C12 C13 119.78(14) ?
N10 C12 C17 121.48(15) ?
C13 C12 C17 118.73(15) ?
N10 C11 C19 122.64(15) ?
N10 C11 C21 116.67(13) ?
C19 C11 C21 120.69(14) ?
O2 C2 N2 121.27(16) y
O2 C2 C1 118.36(13) y
N2 C2 C1 120.37(15) y
C18 C17 C16 122.89(16) ?
C18 C17 C12 117.84(15) ?
C16 C17 C12 119.27(16) ?
C28 C29 C21 119.42(15) ?
C28 C29 H29 120.3 ?
C21 C29 H29 120.3 ?
N3 C3 C1 177.75(17) y
C29 C28 C27 120.28(14) ?
C29 C28 H28 119.9 ?
C27 C28 H28 119.9 ?
C24 C23 C22 120.13(14) ?
C24 C23 H23 119.9 ?
C22 C23 H23 119.9 ?
C25 C26 C27 120.39(15) ?
C25 C26 H26 119.8 ?
C27 C26 H26 119.8 ?
C23 C24 C25 120.76(15) ?
C23 C24 H24 119.6 ?
C25 C24 H24 119.6 ?
C18 C19 C11 119.01(16) ?
C18 C19 H19 120.5 ?
C11 C19 H19 120.5 ?
C26 C25 C24 120.33(16) ?
C26 C25 H25 119.8 ?
C24 C25 H25 119.8 ?
C14 C13 C12 120.33(16) ?
C14 C13 H13 119.8 ?
C12 C13 H13 119.8 ?
N4 C4 C5 179.8(2) ?
C4 C5 H1C5 109.7(14) ?
C4 C5 H3C5 109.1(14) ?
H1C5 C5 H3C5 112.9(19) ?
C4 C5 H2C5 110.4(14) ?
H1C5 C5 H2C5 106.3(19) ?
H3C5 C5 H2C5 108.4(19) ?
C19 C18 C17 120.19(15) ?
C19 C18 H18 119.9 ?
C17 C18 H18 119.9 ?
C15 C16 C17 120.76(17) ?
C15 C16 H16 119.6 ?
C17 C16 H16 119.6 ?
C13 C14 C15 120.89(17) ?
C13 C14 H14 119.6 ?
C15 C14 H14 119.6 ?
C16 C15 C14 119.97(17) ?
C16 C15 H15 120.0 ?
C14 C15 H15 120.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O2 1.9785(10) y
Cu1 N20 1.9912(12) y
Cu1 N1 2.0337(14) y
Cu1 N10 2.2179(13) y
Cu1 Cl1 2.2832(4) y
O2 C2 1.261(2) y
O1 N1 1.2602(17) y
N20 C21 1.331(2) ?
N20 C22 1.371(2) ?
N10 C11 1.331(2) ?
N10 C12 1.370(2) ?
N1 C1 1.334(2) y
N2 C2 1.322(2) y
N2 H2N2 0.82(2) ?
N2 H1N2 0.82(2) ?
N3 C3 1.148(2) y
C21 C29 1.417(2) ?
C21 C11 1.486(2) ?
C22 C23 1.413(2) ?
C22 C27 1.421(2) ?
C27 C28 1.411(2) ?
C27 C26 1.416(2) ?
N4 C4 1.142(2) ?
C1 C3 1.425(2) y
C1 C2 1.456(2) y
C12 C13 1.414(2) ?
C12 C17 1.422(2) ?
C11 C19 1.418(2) ?
C17 C18 1.406(3) ?
C17 C16 1.416(2) ?
C29 C28 1.361(2) ?
C29 H29 0.9500 ?
C28 H28 0.9500 ?
C23 C24 1.365(2) ?
C23 H23 0.9500 ?
C26 C25 1.363(2) ?
C26 H26 0.9500 ?
C24 C25 1.415(2) ?
C24 H24 0.9500 ?
C19 C18 1.359(3) ?
C19 H19 0.9500 ?
C25 H25 0.9500 ?
C13 C14 1.368(2) ?
C13 H13 0.9500 ?
C4 C5 1.455(3) ?
C5 H1C5 0.97(2) ?
C5 H3C5 0.98(2) ?
C5 H2C5 0.99(2) ?
C18 H18 0.9500 ?
C16 C15 1.360(3) ?
C16 H16 0.9500 ?
C14 C15 1.412(3) ?
C14 H14 0.9500 ?
C15 H15 0.9500 ?
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
C19 H19 Cl1 3_766 0.95 2.67 3.4989(17) 146
C13 H13 O2 . 0.95 2.36 3.230(2) 153
N2 H2N2 N3 2_646 0.82(2) 2.53(2) 3.061(2) 123.8(17)
N2 H2N2 N4 2_646 0.82(2) 2.57(2) 3.321(3) 151.3(18)
N2 H1N2 N4 . 0.82(2) 2.20(2) 2.987(2) 161(2)
C5 H1C5 O1 2_646 0.97(2) 2.60(2) 3.541(2) 163.6(18)
C5 H3C5 Cl1 2_656 0.98(2) 2.65(3) 3.615(2) 173.0(19)
C5 H2C5 Cl1 1_455 0.99(2) 2.71(3) 3.688(2) 171.0(19)

_cod_database_fobs_code 2021089
