#------------------------------------------------------------------------------
#$Date: 2017-03-05 07:00:10 +0200 (Sun, 05 Mar 2017) $
#$Revision: 193763 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/73/7227349.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_7227349
loop_
_publ_author_name
'Parra, Nicole'
'Belmar, Julio B.'
'Jiménez, Claudio A.'
'Pasán, Jorge'
'Ruiz-Pérez, Catalina'
_publ_section_title
;
 Crystal structure analysis of supramolecular arrangements in
 bis(1-isoquinolinecarboxamide)alkanes and their Ag(i) complexes
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              1076
_journal_paper_doi               10.1039/C6CE02393B
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'Ag, (C22 H18 N4 O2), (Cl O4)'
_chemical_formula_sum            'C22 H18 Ag Cl N4 O6'
_chemical_formula_weight         577.72
_chemical_name_systematic
;
 ?
;
_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   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-09-23 deposited with the CCDC.
2017-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.472(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7056(2)
_cell_length_b                   14.8087(3)
_cell_length_c                   21.2528(6)
_cell_measurement_reflns_used    6088
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.4450
_cell_measurement_theta_min      3.7480
_cell_volume                     2151.69(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.5953
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12530
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.881
_diffrn_reflns_theta_min         3.795
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.099
_exptl_absorpt_correction_T_max  1.067
_exptl_absorpt_correction_T_min  0.567
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.783
_exptl_crystal_description       needle
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.3312
_exptl_crystal_size_mid          0.0415
_exptl_crystal_size_min          0.0207
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4236
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0276
_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)+(0.0331P)²+1.0968P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0710
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3575
_reflns_number_total             4236
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce02393b2.cif
_cod_data_source_block           compound_I2-Ag
_cod_depositor_comments
'Adding full bibliography for 7227343--7227351.cif.'
_cod_database_code               7227349
_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.
;
_shelxl_version_number           2013-4
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_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
Ag1 Ag 0.74163(3) 1.00508(2) 0.48712(2) 0.04248(8) Uani 1 1 d . .
C1 C 0.6829(4) 0.87546(16) 0.60122(13) 0.0353(5) Uani 1 1 d . .
C2 C 0.5970(3) 0.82793(17) 0.53035(13) 0.0338(5) Uani 1 1 d . .
C3 C 0.5161(3) 0.74015(18) 0.52253(14) 0.0373(5) Uani 1 1 d . .
C4 C 0.5335(4) 0.68678(19) 0.58037(16) 0.0479(7) Uani 1 1 d . .
H4 H 0.6045 0.7079 0.6265 0.057 Uiso 1 1 calc R U
C5 C 0.4451(5) 0.6038(2) 0.56802(18) 0.0572(8) Uani 1 1 d . .
H5 H 0.4574 0.5686 0.6061 0.069 Uiso 1 1 calc R U
C6 C 0.3368(5) 0.5712(2) 0.4990(2) 0.0591(8) Uani 1 1 d . .
H6 H 0.2774 0.5148 0.4917 0.071 Uiso 1 1 calc R U
C7 C 0.3174(4) 0.6205(2) 0.44279(18) 0.0539(8) Uani 1 1 d . .
H7 H 0.2448 0.5978 0.3972 0.065 Uiso 1 1 calc R U
C8 C 0.4062(4) 0.70666(19) 0.45234(15) 0.0425(6) Uani 1 1 d . .
C9 C 0.3871(4) 0.7625(2) 0.39606(15) 0.0477(7) Uani 1 1 d . .
H9 H 0.3142 0.7429 0.3495 0.057 Uiso 1 1 calc R U
C10 C 0.4742(4) 0.8447(2) 0.40914(14) 0.0439(6) Uani 1 1 d . .
H10 H 0.4614 0.8798 0.3710 0.053 Uiso 1 1 calc R U
C11 C 0.9477(4) 0.88858(18) 0.72143(13) 0.0406(6) Uani 1 1 d . .
H11A H 0.9866 0.8393 0.7553 0.049 Uiso 1 1 calc R U
H11B H 0.8517 0.9246 0.7277 0.049 Uiso 1 1 calc R U
C12 C 1.1248(4) 0.94647(18) 0.73672(13) 0.0410(6) Uani 1 1 d . .
H12A H 1.1867 0.9639 0.7863 0.049 Uiso 1 1 calc R U
H12B H 1.2183 0.9111 0.7285 0.049 Uiso 1 1 calc R U
C13 C 1.1217(4) 1.03686(17) 0.64039(13) 0.0344(5) Uani 1 1 d . .
C14 C 1.0730(3) 1.12565(16) 0.60104(13) 0.0332(5) Uani 1 1 d . .
C15 C 1.1730(3) 1.20688(17) 0.63314(14) 0.0360(5) Uani 1 1 d . .
C16 C 1.3109(4) 1.21429(19) 0.70571(15) 0.0430(6) Uani 1 1 d . .
H16 H 1.3412 1.1639 0.7350 0.052 Uiso 1 1 calc R U
C17 C 1.3995(4) 1.2949(2) 0.73271(17) 0.0517(7) Uani 1 1 d . .
H17 H 1.4915 1.2989 0.7802 0.062 Uiso 1 1 calc R U
C18 C 1.3530(4) 1.3720(2) 0.6895(2) 0.0567(8) Uani 1 1 d . .
H18 H 1.4096 1.4272 0.7092 0.068 Uiso 1 1 calc R U
C19 C 1.2262(4) 1.36677(19) 0.61911(19) 0.0536(8) Uani 1 1 d . .
H19 H 1.1996 1.4180 0.5908 0.064 Uiso 1 1 calc R U
C20 C 1.1341(4) 1.28372(18) 0.58862(16) 0.0413(6) Uani 1 1 d . .
C21 C 1.0054(4) 1.2733(2) 0.51593(16) 0.0462(7) Uani 1 1 d . .
H21 H 0.9821 1.3216 0.4851 0.055 Uiso 1 1 calc R U
C22 C 0.9158(4) 1.19345(19) 0.49090(15) 0.0431(6) Uani 1 1 d . .
H22 H 0.8300 1.1885 0.4428 0.052 Uiso 1 1 calc R U
N1 N 0.8589(3) 0.85173(14) 0.65001(11) 0.0398(5) Uani 1 1 d . .
H1 H 0.9236 0.8129 0.6391 0.048 Uiso 1 1 calc R U
N2 N 0.5802(3) 0.87800(14) 0.47636(11) 0.0362(5) Uani 1 1 d . .
N3 N 1.0752(3) 1.02750(15) 0.69296(12) 0.0397(5) Uani 1 1 d . .
H3 H 1.0140 1.0706 0.7014 0.048 Uiso 1 1 calc R U
N4 N 0.9455(3) 1.11959(14) 0.53312(11) 0.0366(5) Uani 1 1 d . .
O1 O 0.5824(3) 0.93239(16) 0.61057(11) 0.0640(7) Uani 1 1 d . .
O2 O 1.2027(4) 0.97849(14) 0.62300(12) 0.0574(6) Uani 1 1 d . .
Cl1 Cl 0.11868(11) 0.62847(4) 0.68354(4) 0.04992(17) Uani 1 1 d . .
O3 O 0.1403(5) 0.71055(18) 0.65288(16) 0.0827(8) Uani 1 1 d . .
O4 O 0.0397(6) 0.6545(2) 0.7298(2) 0.1188(14) Uani 1 1 d . .
O5 O 0.3015(4) 0.5881(2) 0.7233(2) 0.1104(12) Uani 1 1 d . .
O6 O -0.0066(5) 0.5692(2) 0.6325(2) 0.1325(15) Uani 1 1 d . .
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'
Ag Ag 0.1306 4.2820 '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'
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'
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
N2 Ag1 N4 162.02(8) . .
N2 Ag1 O1 86.13(8) . 3_676
N4 Ag1 O1 107.95(8) . 3_676
N2 Ag1 O2 107.95(8) . 3_776
N4 Ag1 O2 86.96(8) . 3_776
O1 Ag1 O2 74.90(7) 3_676 3_776
O1 C1 N1 123.7(2) . .
O1 C1 C2 117.7(2) . .
N1 C1 C2 118.6(2) . .
N2 C2 C3 123.4(2) . .
N2 C2 C1 115.3(2) . .
C3 C2 C1 120.7(2) . .
C4 C3 C2 123.4(2) . .
C4 C3 C8 119.2(3) . .
C2 C3 C8 117.4(3) . .
C5 C4 C3 119.7(3) . .
C5 C4 H4 120.2 . .
C3 C4 H4 120.2 . .
C4 C5 C6 120.9(3) . .
C4 C5 H5 119.5 . .
C6 C5 H5 119.5 . .
C7 C6 C5 120.8(3) . .
C7 C6 H6 119.6 . .
C5 C6 H6 119.6 . .
C6 C7 C8 120.8(3) . .
C6 C7 H7 119.6 . .
C8 C7 H7 119.6 . .
C9 C8 C7 123.6(3) . .
C9 C8 C3 117.8(3) . .
C7 C8 C3 118.6(3) . .
C10 C9 C8 120.4(3) . .
C10 C9 H9 119.8 . .
C8 C9 H9 119.8 . .
C9 C10 N2 122.6(3) . .
C9 C10 H10 118.7 . .
N2 C10 H10 118.7 . .
N1 C11 C12 112.4(2) . .
N1 C11 H11A 109.1 . .
C12 C11 H11A 109.1 . .
N1 C11 H11B 109.1 . .
C12 C11 H11B 109.1 . .
H11A C11 H11B 107.9 . .
N3 C12 C11 112.6(2) . .
N3 C12 H12A 109.1 . .
C11 C12 H12A 109.1 . .
N3 C12 H12B 109.1 . .
C11 C12 H12B 109.1 . .
H12A C12 H12B 107.8 . .
O2 C13 N3 123.7(2) . .
O2 C13 C14 118.7(2) . .
N3 C13 C14 117.5(2) . .
N4 C14 C15 123.1(2) . .
N4 C14 C13 114.5(2) . .
C15 C14 C13 122.0(2) . .
C16 C15 C20 119.0(2) . .
C16 C15 C14 123.8(2) . .
C20 C15 C14 117.2(2) . .
C17 C16 C15 120.3(3) . .
C17 C16 H16 119.9 . .
C15 C16 H16 119.9 . .
C16 C17 C18 120.6(3) . .
C16 C17 H17 119.7 . .
C18 C17 H17 119.7 . .
C19 C18 C17 120.7(3) . .
C19 C18 H18 119.6 . .
C17 C18 H18 119.6 . .
C18 C19 C20 120.4(3) . .
C18 C19 H19 119.8 . .
C20 C19 H19 119.8 . .
C21 C20 C19 123.2(3) . .
C21 C20 C15 118.0(2) . .
C19 C20 C15 118.9(3) . .
C22 C21 C20 120.1(3) . .
C22 C21 H21 119.9 . .
C20 C21 H21 119.9 . .
C21 C22 N4 122.9(3) . .
C21 C22 H22 118.6 . .
N4 C22 H22 118.6 . .
C1 N1 C11 122.6(2) . .
C1 N1 H1 118.7 . .
C11 N1 H1 118.7 . .
C2 N2 C10 118.4(2) . .
C2 N2 Ag1 124.28(17) . .
C10 N2 Ag1 116.84(18) . .
C13 N3 C12 122.0(2) . .
C13 N3 H3 119.0 . .
C12 N3 H3 119.0 . .
C14 N4 C22 118.6(2) . .
C14 N4 Ag1 123.61(17) . .
C22 N4 Ag1 117.03(18) . .
C1 O1 Ag1 124.70(17) . 3_676
C13 O2 Ag1 122.09(17) . 3_776
O6 Cl1 O5 110.3(2) . .
O6 Cl1 O3 111.7(2) . .
O5 Cl1 O3 110.1(2) . .
O6 Cl1 O4 110.3(3) . .
O5 Cl1 O4 109.3(3) . .
O3 Cl1 O4 105.12(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ag1 N2 2.209(2) .
Ag1 N4 2.210(2) .
Ag1 O1 2.573(2) 3_676
Ag1 O2 2.578(2) 3_776
C1 O1 1.222(3) .
C1 N1 1.319(3) .
C1 C2 1.511(3) .
C2 N2 1.321(3) .
C2 C3 1.418(4) .
C3 C4 1.415(4) .
C3 C8 1.422(4) .
C4 C5 1.371(4) .
C4 H4 0.9300 .
C5 C6 1.397(5) .
C5 H5 0.9300 .
C6 C7 1.348(5) .
C6 H6 0.9300 .
C7 C8 1.417(4) .
C7 H7 0.9300 .
C8 C9 1.405(4) .
C9 C10 1.355(4) .
C9 H9 0.9300 .
C10 N2 1.369(3) .
C10 H10 0.9300 .
C11 N1 1.453(3) .
C11 C12 1.514(4) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 N3 1.457(3) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 O2 1.219(3) .
C13 N3 1.329(3) .
C13 C14 1.510(3) .
C14 N4 1.322(3) .
C14 C15 1.422(4) .
C15 C16 1.417(4) .
C15 C20 1.421(4) .
C16 C17 1.364(4) .
C16 H16 0.9300 .
C17 C18 1.404(5) .
C17 H17 0.9300 .
C18 C19 1.360(5) .
C18 H18 0.9300 .
C19 C20 1.418(4) .
C19 H19 0.9300 .
C20 C21 1.407(4) .
C21 C22 1.349(4) .
C21 H21 0.9300 .
C22 N4 1.365(3) .
C22 H22 0.9300 .
N1 H1 0.8600 .
N3 H3 0.8600 .
O1 Ag1 2.573(2) 3_676
O2 Ag1 2.578(2) 3_776
Cl1 O6 1.383(3) .
Cl1 O5 1.399(3) .
Cl1 O3 1.425(2) .
Cl1 O4 1.428(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
_geom_torsion_site_symmetry_4
O1 C1 C2 N2 71.1(3) .
N1 C1 C2 N2 -110.8(3) .
O1 C1 C2 C3 -100.4(3) .
N1 C1 C2 C3 77.8(3) .
N2 C2 C3 C4 -179.7(2) .
C1 C2 C3 C4 -8.9(4) .
N2 C2 C3 C8 -2.2(4) .
C1 C2 C3 C8 168.6(2) .
C2 C3 C4 C5 177.7(3) .
C8 C3 C4 C5 0.2(4) .
C3 C4 C5 C6 -0.4(5) .
C4 C5 C6 C7 0.3(5) .
C5 C6 C7 C8 0.0(5) .
C6 C7 C8 C9 -178.1(3) .
C6 C7 C8 C3 -0.1(4) .
C4 C3 C8 C9 178.1(2) .
C2 C3 C8 C9 0.5(4) .
C4 C3 C8 C7 0.0(4) .
C2 C3 C8 C7 -177.6(2) .
C7 C8 C9 C10 179.1(3) .
C3 C8 C9 C10 1.1(4) .
C8 C9 C10 N2 -1.3(4) .
N1 C11 C12 N3 64.9(3) .
O2 C13 C14 N4 63.8(3) .
N3 C13 C14 N4 -117.0(3) .
O2 C13 C14 C15 -109.7(3) .
N3 C13 C14 C15 69.5(3) .
N4 C14 C15 C16 -179.5(2) .
C13 C14 C15 C16 -6.7(4) .
N4 C14 C15 C20 -1.1(4) .
C13 C14 C15 C20 171.7(2) .
C20 C15 C16 C17 2.3(4) .
C14 C15 C16 C17 -179.4(2) .
C15 C16 C17 C18 1.1(4) .
C16 C17 C18 C19 -3.3(5) .
C17 C18 C19 C20 1.9(5) .
C18 C19 C20 C21 -178.3(3) .
C18 C19 C20 C15 1.5(4) .
C16 C15 C20 C21 176.3(2) .
C14 C15 C20 C21 -2.2(4) .
C16 C15 C20 C19 -3.6(4) .
C14 C15 C20 C19 178.0(2) .
C19 C20 C21 C22 -177.0(3) .
C15 C20 C21 C22 3.2(4) .
C20 C21 C22 N4 -0.9(4) .
O1 C1 N1 C11 2.8(4) .
C2 C1 N1 C11 -175.3(2) .
C12 C11 N1 C1 -113.5(3) .
C3 C2 N2 C10 2.1(4) .
C1 C2 N2 C10 -169.1(2) .
C3 C2 N2 Ag1 -169.97(17) .
C1 C2 N2 Ag1 18.8(3) .
C9 C10 N2 C2 -0.3(4) .
C9 C10 N2 Ag1 172.3(2) .
O2 C13 N3 C12 2.4(4) .
C14 C13 N3 C12 -176.7(2) .
C11 C12 N3 C13 -107.9(3) .
C15 C14 N4 C22 3.5(4) .
C13 C14 N4 C22 -169.9(2) .
C15 C14 N4 Ag1 -165.94(17) .
C13 C14 N4 Ag1 20.7(3) .
C21 C22 N4 C14 -2.5(4) .
C21 C22 N4 Ag1 167.6(2) .
N1 C1 O1 Ag1 172.01(19) 3_676
C2 C1 O1 Ag1 -9.9(4) 3_676
N3 C13 O2 Ag1 173.88(19) 3_776
C14 C13 O2 Ag1 -7.0(3) 3_776
