# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu6mq
_database_code_depnum_ccdc_archive 'CCDC 1814014'
_audit_update_record             
;
2017-12-29 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_date             2017-12-29T10:27:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
_chemical_formula_moiety         'Cu1, Cl2, (C10 H9 N1 O1)2'
_chemical_formula_sum            'C20 H18 Cl2 Cu N2 O2'
_chemical_formula_weight         452.8

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.7645(3)
_cell_length_b                   12.5214(6)
_cell_length_c                   16.2924(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.847(5)
_cell_angle_gamma                90
_cell_volume                     965.04(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1061
_cell_measurement_theta_min      5.474
_cell_measurement_theta_max      72.414

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.027
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_F_000             462

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        'Fri Oct 17 14:13:32 2014'
;
_exptl_absorpt_correction_T_min  0.98222
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.459
_shelx_estimated_absorpt_T_max   0.919

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_orient_matrix_ub_11      0.2264177
_diffrn_orient_matrix_ub_12      0.0687928
_diffrn_orient_matrix_ub_13      -0.0347963
_diffrn_orient_matrix_ub_21      0.0059338
_diffrn_orient_matrix_ub_22      -0.0789548
_diffrn_orient_matrix_ub_23      -0.0722251
_diffrn_orient_matrix_ub_31      -0.2343485
_diffrn_orient_matrix_ub_32      0.0646077
_diffrn_orient_matrix_ub_33      -0.0512615
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_number            3026
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         7.073
_diffrn_reflns_theta_max         72.117
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.958
_reflns_Friedel_coverage         0
_reflns_number_total             1820
_reflns_number_gt                1492
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        'Fri Oct 17 14:13:32 2014'
;
_computing_cell_refinement       
;
        'Fri Oct 17 14:13:32 2014'
;
_computing_data_reduction        
;
        'Fri Oct 17 14:13:32 2014'
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0642P)²+0.0924P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1820
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1159
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_restrained_S_all      1.05
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.07

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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_
_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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0 0 0 0.0359(2) Uani 1 2 d S . P . .
Cl1 Cl 0.24105(18) 0.13884(6) 0.06103(5) 0.0470(2) Uani 1 1 d . . . . .
C110 C 0.0986(7) -0.1452(2) 0.24296(18) 0.0380(6) Uani 1 1 d . . . . .
N11 N 0.1089(6) -0.09055(19) 0.10070(15) 0.0379(5) Uani 1 1 d . . . . .
C15 C -0.0094(7) -0.1306(3) 0.31928(19) 0.0433(7) Uani 1 1 d . . . . .
C13 C 0.3919(8) -0.2374(3) 0.1566(2) 0.0485(8) Uani 1 1 d . . . . .
C14 C 0.2938(8) -0.2269(3) 0.2309(2) 0.0447(7) Uani 1 1 d . . . . .
C19 C 0.0079(6) -0.0771(2) 0.17547(17) 0.0356(6) Uani 1 1 d . . . . .
C17 C -0.2908(7) 0.0165(3) 0.2601(2) 0.0450(7) Uani 1 1 d . . . . .
C18 C -0.1890(7) 0.0033(2) 0.1863(2) 0.0410(7) Uani 1 1 d . . . . .
C16 C -0.1992(7) -0.0506(3) 0.3279(2) 0.0435(7) Uani 1 1 d . . . . .
C12 C 0.2928(8) -0.1675(3) 0.0921(2) 0.0460(7) Uani 1 1 d . . . . .
O11 O -0.3153(7) -0.0292(2) 0.39828(16) 0.0597(7) Uani 1 1 d . . . . .
C111 C -0.2590(13) -0.1038(4) 0.4647(3) 0.0706(13) Uani 1 1 d . . . . .
H12 H 0.356(8) -0.172(3) 0.042(2) 0.044(9) Uiso 1 1 d . . . . .
H15 H 0.040(8) -0.177(3) 0.360(3) 0.053(10) Uiso 1 1 d . . . . .
H18 H -0.234(8) 0.043(3) 0.145(3) 0.049(11) Uiso 1 1 d . . . . .
H13 H 0.536(8) -0.289(3) 0.149(2) 0.048(10) Uiso 1 1 d . . . . .
H14 H 0.340(8) -0.267(3) 0.271(2) 0.048(10) Uiso 1 1 d . . . . .
H17 H -0.435(9) 0.069(4) 0.266(3) 0.060(12) Uiso 1 1 d . . . . .
H11B H -0.052(11) -0.099(4) 0.482(3) 0.066(13) Uiso 1 1 d . . . . .
H11A H -0.366(14) -0.078(5) 0.510(4) 0.11(2) Uiso 1 1 d . . . . .
H11C H -0.332(11) -0.163(5) 0.451(3) 0.076(17) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu N11 2.011(2) . ?
Cu N11 2.011(2) 3 ?
Cu Cl1 2.2490(7) 3 ?
Cu Cl1 2.2490(7) . ?
C110 C14 1.411(5) . ?
C110 C15 1.413(4) . ?
C110 C19 1.417(4) . ?
N11 C12 1.321(4) . ?
N11 C19 1.373(4) . ?
C15 C16 1.368(5) . ?
C15 H15 0.89(4) . ?
C13 C14 1.355(5) . ?
C13 C12 1.405(5) . ?
C13 H13 0.97(4) . ?
C14 H14 0.83(4) . ?
C19 C18 1.402(4) . ?
C17 C18 1.359(5) . ?
C17 C16 1.415(5) . ?
C17 H17 0.97(4) . ?
C18 H18 0.84(4) . ?
C16 O11 1.358(4) . ?
C12 H12 0.91(4) . ?
O11 C111 1.431(5) . ?
C111 H11B 1.00(5) . ?
C111 H11A 0.99(7) . ?
C111 H11C 0.83(6) . ?

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
_geom_angle_publ_flag
N11 Cu N11 180 . 3 ?
N11 Cu Cl1 89.62(7) . 3 ?
N11 Cu Cl1 90.38(7) 3 3 ?
N11 Cu Cl1 90.38(7) . . ?
N11 Cu Cl1 89.62(7) 3 . ?
Cl1 Cu Cl1 180 3 . ?
C14 C110 C15 122.1(3) . . ?
C14 C110 C19 118.2(3) . . ?
C15 C110 C19 119.7(3) . . ?
C12 N11 C19 119.4(3) . . ?
C12 N11 Cu 115.8(2) . . ?
C19 N11 Cu 124.9(2) . . ?
C16 C15 C110 120.0(3) . . ?
C16 C15 H15 121(3) . . ?
C110 C15 H15 119(3) . . ?
C14 C13 C12 119.1(3) . . ?
C14 C13 H13 121(2) . . ?
C12 C13 H13 120(2) . . ?
C13 C14 C110 119.9(3) . . ?
C13 C14 H14 124(3) . . ?
C110 C14 H14 116(3) . . ?
N11 C19 C18 120.6(3) . . ?
N11 C19 C110 120.5(3) . . ?
C18 C19 C110 118.8(3) . . ?
C18 C17 C16 120.6(3) . . ?
C18 C17 H17 120(3) . . ?
C16 C17 H17 119(3) . . ?
C17 C18 C19 120.8(3) . . ?
C17 C18 H18 123(3) . . ?
C19 C18 H18 116(3) . . ?
O11 C16 C15 124.9(3) . . ?
O11 C16 C17 115.1(3) . . ?
C15 C16 C17 120.0(3) . . ?
N11 C12 C13 122.9(3) . . ?
N11 C12 H12 116(2) . . ?
C13 C12 H12 121(2) . . ?
C16 O11 C111 116.8(3) . . ?
O11 C111 H11B 105(3) . . ?
O11 C111 H11A 106(3) . . ?
H11B C111 H11A 110(4) . . ?
O11 C111 H11C 110(4) . . ?
H11B C111 H11C 120(5) . . ?
H11A C111 H11C 105(5) . . ?

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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 C110 C15 C16 -179.7(3) . . . . ?
C19 C110 C15 C16 -0.4(5) . . . . ?
C12 C13 C14 C110 -1.2(5) . . . . ?
C15 C110 C14 C13 -179.7(3) . . . . ?
C19 C110 C14 C13 0.9(5) . . . . ?
C12 N11 C19 C18 -179.5(3) . . . . ?
Cu N11 C19 C18 0.9(4) . . . . ?
C12 N11 C19 C110 -0.2(4) . . . . ?
Cu N11 C19 C110 -179.8(2) . . . . ?
C14 C110 C19 N11 -0.2(4) . . . . ?
C15 C110 C19 N11 -179.6(3) . . . . ?
C14 C110 C19 C18 179.1(3) . . . . ?
C15 C110 C19 C18 -0.3(4) . . . . ?
C16 C17 C18 C19 0.3(5) . . . . ?
N11 C19 C18 C17 179.6(3) . . . . ?
C110 C19 C18 C17 0.3(5) . . . . ?
C110 C15 C16 O11 -179.8(3) . . . . ?
C110 C15 C16 C17 0.9(5) . . . . ?
C18 C17 C16 O11 179.7(3) . . . . ?
C18 C17 C16 C15 -0.9(5) . . . . ?
C19 N11 C12 C13 -0.1(5) . . . . ?
Cu N11 C12 C13 179.6(3) . . . . ?
C14 C13 C12 N11 0.8(6) . . . . ?
C15 C16 O11 C111 -7.6(6) . . . . ?
C17 C16 O11 C111 171.7(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12 Cl1 0.91(4) 2.73(4) 3.551(4) 151(3) 3_655
C15 H15 Cl1 0.89(4) 2.78(4) 3.630(3) 159(3) 2_545
C111 H11A O11 0.99(7) 2.63(7) 3.598(6) 166(5) 3_456


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zn6mq_re-labeled2
_database_code_depnum_ccdc_archive 'CCDC 1814018'
_audit_update_record             
;
2017-12-29 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_date             2017-12-28T10:37:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'Zn1, Cl2, (C10 H9 N1 O1)2'
_chemical_formula_sum            'C20 H18 Cl2 N2 O2 Zn'
_chemical_formula_weight         454.63

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.3857(4)
_cell_length_b                   15.2082(6)
_cell_length_c                   12.5660(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.344(4)
_cell_angle_gamma                90
_cell_volume                     1984.23(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    4622
_cell_measurement_theta_min      4.067
_cell_measurement_theta_max      28.176

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.136
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_F_000             928

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.65788
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_orient_matrix_ub_11      0.0120075
_diffrn_orient_matrix_ub_12      -0.0454968
_diffrn_orient_matrix_ub_13      0.0075866
_diffrn_orient_matrix_ub_21      -0.0538237
_diffrn_orient_matrix_ub_22      -0.0028145
_diffrn_orient_matrix_ub_23      0.0335635
_diffrn_orient_matrix_ub_31      -0.0402366
_diffrn_orient_matrix_ub_32      -0.0098196
_diffrn_orient_matrix_ub_33      -0.0448302
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_number            17617
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.132
_diffrn_reflns_theta_max         29.558
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.872
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.872
_reflns_Friedel_coverage         0
_reflns_number_total             4850
_reflns_number_gt                3489
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0600P)²+0.8165P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4850
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.133
_refine_ls_wR_factor_gt          0.1126
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.729
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.084

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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_
_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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.20281(3) 0.08653(2) 0.80117(3) 0.04264(14) Uani 1 1 d . . . . .
Cl1 Cl 0.10351(9) 0.12497(6) 0.95068(7) 0.0555(2) Uani 1 1 d . . . . .
Cl2 Cl 0.26072(10) 0.19868(5) 0.69840(8) 0.0621(3) Uani 1 1 d . . . . .
N11 N 0.0869(2) -0.00420(16) 0.7224(2) 0.0390(5) Uani 1 1 d . . . . .
N21 N 0.3693(2) 0.01593(16) 0.8357(2) 0.0406(6) Uani 1 1 d . . . . .
C28 C 0.2604(3) -0.0913(2) 0.9434(3) 0.0432(7) Uani 1 1 d . . . . .
C16 C 0.1686(3) -0.1126(2) 0.4255(3) 0.0475(7) Uani 1 1 d . . . . .
C110 C 0.0354(3) -0.10652(19) 0.5793(2) 0.0396(6) Uani 1 1 d . . . . .
C19 C 0.1136(3) -0.03941(18) 0.6241(2) 0.0376(6) Uani 1 1 d . . . . .
C22 C 0.4784(3) 0.0458(2) 0.7967(3) 0.0457(7) Uani 1 1 d . . . . .
C210 C 0.4903(3) -0.1026(2) 0.9192(2) 0.0426(7) Uani 1 1 d . . . . .
C18 C 0.2196(3) -0.0095(2) 0.5666(3) 0.0463(7) Uani 1 1 d . . . . .
O11 O 0.2097(3) -0.14263(18) 0.3300(2) 0.0661(7) Uani 1 1 d . . . . .
C29 C 0.3736(3) -0.05794(19) 0.8980(2) 0.0373(6) Uani 1 1 d . . . . .
C27 C 0.2643(3) -0.1639(2) 1.0057(3) 0.0492(8) Uani 1 1 d . . . . .
O21 O 0.3710(3) -0.27978(16) 1.0913(2) 0.0714(8) Uani 1 1 d . . . . .
C17 C 0.2457(3) -0.0446(2) 0.4708(3) 0.0510(8) Uani 1 1 d . . . . .
C12 C -0.0124(3) -0.0350(2) 0.7743(3) 0.0455(7) Uani 1 1 d . . . . .
C15 C 0.0656(3) -0.1418(2) 0.4781(3) 0.0465(7) Uani 1 1 d . . . . .
C24 C 0.6032(3) -0.0672(3) 0.8770(3) 0.0526(8) Uani 1 1 d . . . . .
C14 C -0.0672(3) -0.1378(2) 0.6388(3) 0.0489(8) Uani 1 1 d . . . . .
C23 C 0.5968(3) 0.0059(2) 0.8160(3) 0.0520(8) Uani 1 1 d . . . . .
C13 C -0.0907(3) -0.1023(2) 0.7358(3) 0.0534(9) Uani 1 1 d . . . . .
C26 C 0.3817(4) -0.2088(2) 1.0267(3) 0.0505(8) Uani 1 1 d . . . . .
C25 C 0.4918(4) -0.1785(2) 0.9840(3) 0.0523(8) Uani 1 1 d . . . . .
C211 C 0.4850(5) -0.3280(3) 1.1159(5) 0.0987(18) Uani 1 1 d . . . . .
H211 H 0.4648 -0.3762 1.1619 0.148 Uiso 1 1 calc R U . . .
H213 H 0.5206 -0.3502 1.0514 0.148 Uiso 1 1 calc R U . . .
H212 H 0.5465 -0.2902 1.151 0.148 Uiso 1 1 calc R U . . .
C111 C 0.1354(6) -0.2121(3) 0.2816(3) 0.0709(12) Uani 1 1 d . . . . .
H22 H 0.471(3) 0.0972(18) 0.758(2) 0.030(7) Uiso 1 1 d . . . . .
H27 H 0.183(3) -0.189(2) 1.043(3) 0.051(9) Uiso 1 1 d . . . . .
H23 H 0.671(3) 0.029(2) 0.786(3) 0.050(9) Uiso 1 1 d . . . . .
H13 H -0.157(3) -0.124(2) 0.775(3) 0.048(9) Uiso 1 1 d . . . . .
H17 H 0.313(3) -0.028(2) 0.431(3) 0.055(10) Uiso 1 1 d . . . . .
H12 H -0.030(3) -0.009(2) 0.836(3) 0.042(9) Uiso 1 1 d . . . . .
H14 H -0.117(3) -0.179(2) 0.609(3) 0.056(10) Uiso 1 1 d . . . . .
H28 H 0.179(4) -0.060(2) 0.934(3) 0.057(10) Uiso 1 1 d . . . . .
H15 H 0.012(4) -0.184(3) 0.451(3) 0.069(12) Uiso 1 1 d . . . . .
H25 H 0.567(4) -0.204(2) 0.996(3) 0.062(11) Uiso 1 1 d . . . . .
H18 H 0.266(3) 0.033(2) 0.593(3) 0.055(10) Uiso 1 1 d . . . . .
H24 H 0.680(4) -0.096(2) 0.892(3) 0.065(11) Uiso 1 1 d . . . . .
H111 H 0.132(4) -0.267(3) 0.328(4) 0.083(13) Uiso 1 1 d . . . . .
H113 H 0.193(5) -0.224(3) 0.231(4) 0.094(17) Uiso 1 1 d . . . . .
H112 H 0.057(5) -0.187(3) 0.253(4) 0.091(15) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N11 2.068(2) . ?
Zn1 N21 2.072(2) . ?
Zn1 Cl2 2.2305(9) . ?
Zn1 Cl1 2.2418(9) . ?
N11 C12 1.319(4) . ?
N11 C19 1.380(4) . ?
N21 C22 1.325(4) . ?
N21 C29 1.370(4) . ?
C28 C27 1.352(4) . ?
C28 C29 1.413(4) . ?
C28 H28 0.98(4) . ?
C16 C15 1.346(5) . ?
C16 O11 1.363(4) . ?
C16 C17 1.419(5) . ?
C110 C14 1.399(4) . ?
C110 C19 1.413(4) . ?
C110 C15 1.422(4) . ?
C19 C18 1.407(4) . ?
C22 C23 1.388(5) . ?
C22 H22 0.92(3) . ?
C210 C24 1.406(5) . ?
C210 C29 1.409(4) . ?
C210 C25 1.414(5) . ?
C18 C17 1.350(5) . ?
C18 H18 0.87(4) . ?
O11 C111 1.435(5) . ?
C27 C26 1.417(5) . ?
C27 H27 1.05(3) . ?
O21 C26 1.356(4) . ?
O21 C211 1.420(5) . ?
C17 H17 0.91(4) . ?
C12 C13 1.387(5) . ?
C12 H12 0.90(3) . ?
C15 H15 0.91(4) . ?
C24 C23 1.351(5) . ?
C24 H24 0.93(4) . ?
C14 C13 1.360(5) . ?
C14 H14 0.88(4) . ?
C23 H23 0.94(3) . ?
C13 H13 0.91(3) . ?
C26 C25 1.356(5) . ?
C25 H25 0.88(4) . ?
C211 H211 0.96 . ?
C211 H213 0.96 . ?
C211 H212 0.96 . ?
C111 H111 1.01(5) . ?
C111 H113 0.90(5) . ?
C111 H112 0.96(5) . ?

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
_geom_angle_publ_flag
N11 Zn1 N21 103.16(9) . . ?
N11 Zn1 Cl2 113.26(7) . . ?
N21 Zn1 Cl2 106.40(7) . . ?
N11 Zn1 Cl1 107.53(7) . . ?
N21 Zn1 Cl1 110.96(7) . . ?
Cl2 Zn1 Cl1 114.92(4) . . ?
C12 N11 C19 118.7(3) . . ?
C12 N11 Zn1 117.0(2) . . ?
C19 N11 Zn1 124.11(19) . . ?
C22 N21 C29 118.4(3) . . ?
C22 N21 Zn1 117.5(2) . . ?
C29 N21 Zn1 124.1(2) . . ?
C27 C28 C29 120.9(3) . . ?
C27 C28 H28 119(2) . . ?
C29 C28 H28 120(2) . . ?
C15 C16 O11 126.3(3) . . ?
C15 C16 C17 119.4(3) . . ?
O11 C16 C17 114.3(3) . . ?
C14 C110 C19 118.1(3) . . ?
C14 C110 C15 122.4(3) . . ?
C19 C110 C15 119.5(3) . . ?
N11 C19 C18 120.6(3) . . ?
N11 C19 C110 120.8(3) . . ?
C18 C19 C110 118.6(3) . . ?
N21 C22 C23 123.2(3) . . ?
N21 C22 H22 114.7(18) . . ?
C23 C22 H22 122.0(18) . . ?
C24 C210 C29 117.8(3) . . ?
C24 C210 C25 122.1(3) . . ?
C29 C210 C25 120.0(3) . . ?
C17 C18 C19 120.4(3) . . ?
C17 C18 H18 121(2) . . ?
C19 C18 H18 119(2) . . ?
C16 O11 C111 116.3(3) . . ?
N21 C29 C210 121.3(3) . . ?
N21 C29 C28 120.6(3) . . ?
C210 C29 C28 118.1(3) . . ?
C28 C27 C26 121.0(3) . . ?
C28 C27 H27 122.8(18) . . ?
C26 C27 H27 116.2(18) . . ?
C26 O21 C211 117.5(3) . . ?
C18 C17 C16 121.5(3) . . ?
C18 C17 H17 124(2) . . ?
C16 C17 H17 114(2) . . ?
N11 C12 C13 123.3(3) . . ?
N11 C12 H12 117(2) . . ?
C13 C12 H12 120(2) . . ?
C16 C15 C110 120.6(3) . . ?
C16 C15 H15 122(3) . . ?
C110 C15 H15 117(3) . . ?
C23 C24 C210 119.9(3) . . ?
C23 C24 H24 123(2) . . ?
C210 C24 H24 118(2) . . ?
C13 C14 C110 119.9(3) . . ?
C13 C14 H14 123(2) . . ?
C110 C14 H14 117(2) . . ?
C24 C23 C22 119.4(3) . . ?
C24 C23 H23 121(2) . . ?
C22 C23 H23 120(2) . . ?
C14 C13 C12 119.3(3) . . ?
C14 C13 H13 119(2) . . ?
C12 C13 H13 121(2) . . ?
C25 C26 O21 126.1(3) . . ?
C25 C26 C27 119.5(3) . . ?
O21 C26 C27 114.4(3) . . ?
C26 C25 C210 120.5(3) . . ?
C26 C25 H25 122(2) . . ?
C210 C25 H25 117(3) . . ?
O21 C211 H211 109.5 . . ?
O21 C211 H213 109.5 . . ?
H211 C211 H213 109.5 . . ?
O21 C211 H212 109.5 . . ?
H211 C211 H212 109.5 . . ?
H213 C211 H212 109.5 . . ?
O11 C111 H111 112(2) . . ?
O11 C111 H113 95(3) . . ?
H111 C111 H113 106(4) . . ?
O11 C111 H112 108(3) . . ?
H111 C111 H112 120(4) . . ?
H113 C111 H112 112(4) . . ?

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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N11 C19 C18 -179.0(3) . . . . ?
Zn1 N11 C19 C18 -4.9(4) . . . . ?
C12 N11 C19 C110 0.6(4) . . . . ?
Zn1 N11 C19 C110 174.70(19) . . . . ?
C14 C110 C19 N11 -1.8(4) . . . . ?
C15 C110 C19 N11 -179.7(3) . . . . ?
C14 C110 C19 C18 177.8(3) . . . . ?
C15 C110 C19 C18 0.0(4) . . . . ?
C29 N21 C22 C23 0.1(5) . . . . ?
Zn1 N21 C22 C23 178.5(3) . . . . ?
N11 C19 C18 C17 179.6(3) . . . . ?
C110 C19 C18 C17 -0.1(4) . . . . ?
C15 C16 O11 C111 -0.1(5) . . . . ?
C17 C16 O11 C111 179.4(3) . . . . ?
C22 N21 C29 C210 -1.2(4) . . . . ?
Zn1 N21 C29 C210 -179.5(2) . . . . ?
C22 N21 C29 C28 178.6(3) . . . . ?
Zn1 N21 C29 C28 0.3(4) . . . . ?
C24 C210 C29 N21 2.1(4) . . . . ?
C25 C210 C29 N21 179.8(3) . . . . ?
C24 C210 C29 C28 -177.7(3) . . . . ?
C25 C210 C29 C28 0.0(4) . . . . ?
C27 C28 C29 N21 -179.5(3) . . . . ?
C27 C28 C29 C210 0.3(4) . . . . ?
C29 C28 C27 C26 -0.4(5) . . . . ?
C19 C18 C17 C16 -0.5(5) . . . . ?
C15 C16 C17 C18 1.3(5) . . . . ?
O11 C16 C17 C18 -178.2(3) . . . . ?
C19 N11 C12 C13 1.1(5) . . . . ?
Zn1 N11 C12 C13 -173.4(3) . . . . ?
O11 C16 C15 C110 178.0(3) . . . . ?
C17 C16 C15 C110 -1.4(5) . . . . ?
C14 C110 C15 C16 -177.0(3) . . . . ?
C19 C110 C15 C16 0.8(4) . . . . ?
C29 C210 C24 C23 -1.8(5) . . . . ?
C25 C210 C24 C23 -179.5(3) . . . . ?
C19 C110 C14 C13 1.4(5) . . . . ?
C15 C110 C14 C13 179.2(3) . . . . ?
C210 C24 C23 C22 0.8(5) . . . . ?
N21 C22 C23 C24 0.2(5) . . . . ?
C110 C14 C13 C12 0.2(5) . . . . ?
N11 C12 C13 C14 -1.5(5) . . . . ?
C211 O21 C26 C25 -1.0(5) . . . . ?
C211 O21 C26 C27 -179.9(4) . . . . ?
C28 C27 C26 C25 0.2(5) . . . . ?
C28 C27 C26 O21 179.3(3) . . . . ?
O21 C26 C25 C210 -178.8(3) . . . . ?
C27 C26 C25 C210 0.1(5) . . . . ?
C24 C210 C25 C26 177.5(3) . . . . ?
C29 C210 C25 C26 -0.2(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C22 H22 Cl2 0.92(3) 2.76(3) 3.451(4) 133(2) .
C23 H23 O11 0.94(3) 2.59(3) 3.449(5) 153(3) 3_656
C13 H13 Cl2 0.91(3) 2.93(3) 3.610(4) 133(3) 2_546
C12 H12 Cl1 0.90(3) 2.84(3) 3.487(4) 130(3) .
C28 H28 Cl1 0.98(4) 2.92(4) 3.673(3) 134(3) .
C18 H18 Cl2 0.87(4) 2.85(4) 3.594(4) 145(3) .
C22 H22 Cl2 0.92(3) 2.76(3) 3.451(4) 133(2) .
C23 H23 O11 0.94(3) 2.59(3) 3.449(5) 153(3) 3_656
C13 H13 Cl2 0.91(3) 2.93(3) 3.610(4) 133(3) 2_546
C12 H12 Cl1 0.90(3) 2.84(3) 3.487(4) 130(3) .
C28 H28 Cl1 0.98(4) 2.92(4) 3.673(3) 134(3) .
C18 H18 Cl2 0.87(4) 2.85(4) 3.594(4) 145(3) .

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_co6mq
_database_code_depnum_ccdc_archive 'CCDC 1814017'
_audit_update_record             
;
2017-12-29 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_date             2017-12-28T15:05:37-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'Co1, Cl3, (C10 H9 N1 O1), (C10 H10 N1 O1)'
_chemical_formula_sum            'C20 H19 Cl3 Co N2 O2'
_chemical_formula_weight         484.65

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4148(3)
_cell_length_b                   9.4514(4)
_cell_length_c                   15.8456(9)
_cell_angle_alpha                104.570(4)
_cell_angle_beta                 91.426(4)
_cell_angle_gamma                104.996(4)
_cell_volume                     1033.33(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2508
_cell_measurement_theta_min      2.9593
_cell_measurement_theta_max      29.113

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.359
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.033
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_F_000             494

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.95527
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.0604
_diffrn_orient_matrix_ub_11      -0.0041604
_diffrn_orient_matrix_ub_12      -0.0782744
_diffrn_orient_matrix_ub_13      -0.0092838
_diffrn_orient_matrix_ub_21      -0.0123144
_diffrn_orient_matrix_ub_22      -0.0066501
_diffrn_orient_matrix_ub_23      -0.0455027
_diffrn_orient_matrix_ub_31      0.0986415
_diffrn_orient_matrix_ub_32      0.0181419
_diffrn_orient_matrix_ub_33      -0.0015614
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_number            8344
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.965
_diffrn_reflns_theta_max         29.177
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.842
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.842
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.842
_reflns_Friedel_coverage         0
_reflns_number_total             4698
_reflns_number_gt                3588
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0312P)²+0.2267P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4698
_refine_ls_number_parameters     329
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.086
_refine_ls_wR_factor_gt          0.0776
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.055

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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_
_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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.79845(4) 0.00686(3) 0.19338(2) 0.03478(10) Uani 1 1 d . . . . .
Cl1 Cl 1.01042(9) -0.09975(7) 0.12033(5) 0.04840(18) Uani 1 1 d . . . . .
Cl2 Cl 0.50698(8) -0.11040(7) 0.12406(5) 0.04938(18) Uani 1 1 d . . . . .
Cl3 Cl 0.80584(11) -0.00669(9) 0.33235(5) 0.0614(2) Uani 1 1 d . . . . .
C110 C 0.9905(3) 0.4945(2) 0.20208(15) 0.0318(5) Uani 1 1 d . . . . .
O21 O 0.7189(3) 0.5817(2) 0.45707(12) 0.0551(5) Uani 1 1 d . . . . .
N11 N 0.8577(2) 0.2203(2) 0.17075(12) 0.0317(4) Uani 1 1 d . . . . .
O11 O 1.2585(3) 0.7562(2) 0.40558(13) 0.0589(5) Uani 1 1 d . . . . .
C210 C 0.4975(3) 0.4566(2) 0.23093(15) 0.0321(5) Uani 1 1 d . . . . .
C13 C 0.8274(3) 0.3508(3) 0.06137(17) 0.0385(6) Uani 1 1 d . . . . .
C19 C 0.9561(3) 0.3565(2) 0.22687(15) 0.0291(5) Uani 1 1 d . . . . .
C25 C 0.5946(3) 0.5558(3) 0.31019(16) 0.0358(5) Uani 1 1 d . . . . .
N21 N 0.3402(3) 0.2047(3) 0.14766(15) 0.0454(5) Uani 1 1 d . . . . .
C29 C 0.4367(3) 0.2990(3) 0.22438(16) 0.0347(5) Uani 1 1 d . . . . .
C27 C 0.5701(4) 0.3401(3) 0.36873(19) 0.0464(7) Uani 1 1 d . . . . .
C28 C 0.4755(4) 0.2425(3) 0.29420(19) 0.0462(6) Uani 1 1 d . . . . .
C14 C 0.9217(3) 0.4870(3) 0.11712(17) 0.0380(6) Uani 1 1 d . . . . .
C16 C 1.1573(3) 0.6325(3) 0.34234(17) 0.0403(6) Uani 1 1 d . . . . .
C15 C 1.0922(3) 0.6323(3) 0.26156(17) 0.0385(6) Uani 1 1 d . . . . .
C24 C 0.4548(3) 0.5054(3) 0.15766(17) 0.0410(6) Uani 1 1 d . . . . .
C12 C 0.7979(3) 0.2207(3) 0.09108(16) 0.0353(5) Uani 1 1 d . . . . .
C22 C 0.3002(4) 0.2512(4) 0.07973(19) 0.0501(7) Uani 1 1 d . . . . .
C26 C 0.6290(3) 0.4988(3) 0.37775(16) 0.0390(6) Uani 1 1 d . . . . .
C18 C 1.0252(3) 0.3615(3) 0.31165(16) 0.0384(6) Uani 1 1 d . . . . .
C17 C 1.1225(4) 0.4954(3) 0.36783(18) 0.0435(6) Uani 1 1 d . . . . .
C23 C 0.3585(4) 0.4036(3) 0.08321(19) 0.0487(7) Uani 1 1 d . . . . .
C211 C 0.7823(5) 0.7434(4) 0.4713(2) 0.0631(9) Uani 1 1 d D . . . .
C111 C 1.3012(6) 0.8987(3) 0.3839(3) 0.0743(11) Uani 1 1 d D . . . .
H25 H 0.631(3) 0.662(3) 0.3124(17) 0.046(7) Uiso 1 1 d . . . . .
H24 H 0.489(3) 0.615(3) 0.1618(16) 0.043(7) Uiso 1 1 d . . . . .
H14 H 0.939(3) 0.575(3) 0.1015(16) 0.040(7) Uiso 1 1 d . . . . .
H12 H 0.731(3) 0.127(3) 0.0541(15) 0.035(6) Uiso 1 1 d . . . . .
H18 H 1.004(3) 0.270(3) 0.3256(16) 0.042(7) Uiso 1 1 d . . . . .
H13 H 0.781(3) 0.340(3) -0.0004(17) 0.049(7) Uiso 1 1 d . . . . .
H28 H 0.448(3) 0.140(3) 0.2860(17) 0.050(8) Uiso 1 1 d . . . . .
H15 H 1.110(3) 0.718(3) 0.2460(16) 0.040(7) Uiso 1 1 d . . . . .
H23 H 0.332(3) 0.432(3) 0.0337(18) 0.047(7) Uiso 1 1 d . . . . .
H21 H 0.295(4) 0.111(4) 0.146(2) 0.067(10) Uiso 1 1 d . . . . .
H17 H 1.162(3) 0.496(3) 0.4239(18) 0.050(8) Uiso 1 1 d . . . . .
H22 H 0.234(4) 0.178(3) 0.030(2) 0.059(8) Uiso 1 1 d . . . . .
H27 H 0.597(4) 0.313(3) 0.4125(19) 0.062(9) Uiso 1 1 d . . . . .
H211 H 0.674(3) 0.784(3) 0.4698(19) 0.076(11) Uiso 1 1 d D . . . .
H212 H 0.842(4) 0.783(3) 0.5305(12) 0.082(10) Uiso 1 1 d D . . . .
H213 H 0.869(3) 0.772(3) 0.4314(16) 0.071(10) Uiso 1 1 d D . . . .
H111 H 1.379(4) 0.964(3) 0.4335(15) 0.090(11) Uiso 1 1 d D . . . .
H112 H 1.192(3) 0.926(4) 0.371(2) 0.085(12) Uiso 1 1 d D . . . .
H113 H 1.369(5) 0.888(5) 0.3324(17) 0.123(18) Uiso 1 1 d D . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N11 2.0745(18) . ?
Co1 Cl3 2.2379(8) . ?
Co1 Cl2 2.2661(6) . ?
Co1 Cl1 2.2691(7) . ?
C110 C14 1.406(3) . ?
C110 C15 1.411(3) . ?
C110 C19 1.418(3) . ?
O21 C26 1.353(3) . ?
O21 C211 1.434(4) . ?
N11 C12 1.329(3) . ?
N11 C19 1.374(3) . ?
O11 C16 1.362(3) . ?
O11 C111 1.432(4) . ?
C210 C24 1.410(3) . ?
C210 C25 1.410(3) . ?
C210 C29 1.416(3) . ?
C13 C14 1.363(3) . ?
C13 C12 1.392(3) . ?
C13 H13 1.00(3) . ?
C19 C18 1.411(3) . ?
C25 C26 1.360(3) . ?
C25 H25 0.96(3) . ?
N21 C22 1.315(4) . ?
N21 C29 1.366(3) . ?
N21 H21 0.86(3) . ?
C29 C28 1.398(3) . ?
C27 C28 1.347(4) . ?
C27 C26 1.418(3) . ?
C27 H27 0.84(3) . ?
C28 H28 0.91(3) . ?
C14 H14 0.90(2) . ?
C16 C15 1.357(3) . ?
C16 C17 1.415(3) . ?
C15 H15 0.88(2) . ?
C24 C23 1.363(4) . ?
C24 H24 0.98(2) . ?
C12 H12 0.93(2) . ?
C22 C23 1.379(4) . ?
C22 H22 0.93(3) . ?
C18 C17 1.358(3) . ?
C18 H18 0.92(3) . ?
C17 H17 0.93(3) . ?
C23 H23 0.92(3) . ?
C211 H211 0.977(17) . ?
C211 H212 0.966(17) . ?
C211 H213 0.949(16) . ?
C111 H111 0.938(17) . ?
C111 H112 0.946(17) . ?
C111 H113 0.966(17) . ?

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
_geom_angle_publ_flag
N11 Co1 Cl3 118.15(6) . . ?
N11 Co1 Cl2 103.38(5) . . ?
Cl3 Co1 Cl2 110.22(3) . . ?
N11 Co1 Cl1 103.63(6) . . ?
Cl3 Co1 Cl1 111.14(3) . . ?
Cl2 Co1 Cl1 109.80(3) . . ?
C14 C110 C15 122.4(2) . . ?
C14 C110 C19 117.5(2) . . ?
C15 C110 C19 120.0(2) . . ?
C26 O21 C211 117.3(2) . . ?
C12 N11 C19 117.87(19) . . ?
C12 N11 Co1 114.59(15) . . ?
C19 N11 Co1 127.49(14) . . ?
C16 O11 C111 116.6(2) . . ?
C24 C210 C25 123.8(2) . . ?
C24 C210 C29 117.7(2) . . ?
C25 C210 C29 118.5(2) . . ?
C14 C13 C12 118.6(2) . . ?
C14 C13 H13 122.6(15) . . ?
C12 C13 H13 118.8(15) . . ?
N11 C19 C18 119.97(19) . . ?
N11 C19 C110 121.66(19) . . ?
C18 C19 C110 118.4(2) . . ?
C26 C25 C210 119.8(2) . . ?
C26 C25 H25 124.3(16) . . ?
C210 C25 H25 115.9(15) . . ?
C22 N21 C29 124.1(2) . . ?
C22 N21 H21 118(2) . . ?
C29 N21 H21 118(2) . . ?
N21 C29 C28 121.4(2) . . ?
N21 C29 C210 117.8(2) . . ?
C28 C29 C210 120.8(2) . . ?
C28 C27 C26 121.2(2) . . ?
C28 C27 H27 123(2) . . ?
C26 C27 H27 115(2) . . ?
C27 C28 C29 119.2(2) . . ?
C27 C28 H28 121.4(17) . . ?
C29 C28 H28 119.0(17) . . ?
C13 C14 C110 120.3(2) . . ?
C13 C14 H14 121.6(16) . . ?
C110 C14 H14 118.0(16) . . ?
C15 C16 O11 126.1(2) . . ?
C15 C16 C17 120.4(2) . . ?
O11 C16 C17 113.5(2) . . ?
C16 C15 C110 119.9(2) . . ?
C16 C15 H15 120.8(16) . . ?
C110 C15 H15 119.3(16) . . ?
C23 C24 C210 120.8(2) . . ?
C23 C24 H24 119.9(15) . . ?
C210 C24 H24 119.1(15) . . ?
N11 C12 C13 124.0(2) . . ?
N11 C12 H12 116.6(14) . . ?
C13 C12 H12 119.3(14) . . ?
N21 C22 C23 119.9(3) . . ?
N21 C22 H22 117.7(18) . . ?
C23 C22 H22 122.4(18) . . ?
O21 C26 C25 125.5(2) . . ?
O21 C26 C27 114.0(2) . . ?
C25 C26 C27 120.5(2) . . ?
C17 C18 C19 120.6(2) . . ?
C17 C18 H18 122.6(15) . . ?
C19 C18 H18 116.7(15) . . ?
C18 C17 C16 120.7(2) . . ?
C18 C17 H17 118.9(17) . . ?
C16 C17 H17 120.4(17) . . ?
C24 C23 C22 119.7(3) . . ?
C24 C23 H23 122.6(16) . . ?
C22 C23 H23 117.7(16) . . ?
O21 C211 H211 109.2(19) . . ?
O21 C211 H212 105.9(19) . . ?
H211 C211 H212 107(2) . . ?
O21 C211 H213 112.1(19) . . ?
H211 C211 H213 113(2) . . ?
H212 C211 H213 110(2) . . ?
O11 C111 H111 102(2) . . ?
O11 C111 H112 112(2) . . ?
H111 C111 H112 115(3) . . ?
O11 C111 H113 107(3) . . ?
H111 C111 H113 112(3) . . ?
H112 C111 H113 108(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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N11 C19 C18 -179.0(2) . . . . ?
Co1 N11 C19 C18 -1.7(3) . . . . ?
C12 N11 C19 C110 1.2(3) . . . . ?
Co1 N11 C19 C110 178.41(16) . . . . ?
C14 C110 C19 N11 -0.6(3) . . . . ?
C15 C110 C19 N11 180.0(2) . . . . ?
C14 C110 C19 C18 179.5(2) . . . . ?
C15 C110 C19 C18 0.1(3) . . . . ?
C24 C210 C25 C26 179.7(2) . . . . ?
C29 C210 C25 C26 0.6(4) . . . . ?
C22 N21 C29 C28 -179.8(3) . . . . ?
C22 N21 C29 C210 -0.1(4) . . . . ?
C24 C210 C29 N21 -0.2(3) . . . . ?
C25 C210 C29 N21 178.9(2) . . . . ?
C24 C210 C29 C28 179.5(2) . . . . ?
C25 C210 C29 C28 -1.4(3) . . . . ?
C26 C27 C28 C29 0.7(4) . . . . ?
N21 C29 C28 C27 -179.6(3) . . . . ?
C210 C29 C28 C27 0.8(4) . . . . ?
C12 C13 C14 C110 1.3(4) . . . . ?
C15 C110 C14 C13 178.7(2) . . . . ?
C19 C110 C14 C13 -0.7(3) . . . . ?
C111 O11 C16 C15 -0.7(4) . . . . ?
C111 O11 C16 C17 179.2(3) . . . . ?
O11 C16 C15 C110 179.3(2) . . . . ?
C17 C16 C15 C110 -0.7(4) . . . . ?
C14 C110 C15 C16 -179.2(2) . . . . ?
C19 C110 C15 C16 0.2(4) . . . . ?
C25 C210 C24 C23 -179.2(2) . . . . ?
C29 C210 C24 C23 -0.2(4) . . . . ?
C19 N11 C12 C13 -0.6(3) . . . . ?
Co1 N11 C12 C13 -178.13(19) . . . . ?
C14 C13 C12 N11 -0.7(4) . . . . ?
C29 N21 C22 C23 0.8(4) . . . . ?
C211 O21 C26 C25 0.4(4) . . . . ?
C211 O21 C26 C27 -179.8(3) . . . . ?
C210 C25 C26 O21 -179.4(2) . . . . ?
C210 C25 C26 C27 0.8(4) . . . . ?
C28 C27 C26 O21 178.7(3) . . . . ?
C28 C27 C26 C25 -1.5(4) . . . . ?
N11 C19 C18 C17 -179.9(2) . . . . ?
C110 C19 C18 C17 -0.1(4) . . . . ?
C19 C18 C17 C16 -0.3(4) . . . . ?
C15 C16 C17 C18 0.7(4) . . . . ?
O11 C16 C17 C18 -179.2(2) . . . . ?
C210 C24 C23 C22 0.8(4) . . . . ?
N21 C22 C23 C24 -1.1(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N21 H21 Cl1 0.86(3) 2.44(3) 3.182(2) 145(3) 1_455
N21 H21 Cl2 0.86(3) 2.88(3) 3.451(2) 125(2) .
C12 H12 Cl2 0.93(2) 2.91(2) 3.479(2) 121.0(17) .
C18 H18 Cl3 0.92(3) 2.68(3) 3.541(3) 156(2) .
C13 H13 Cl2 1.00(3) 2.89(2) 3.648(3) 132.8(18) 2_655
C14 H14 Cl1 0.90(2) 2.92(3) 3.776(2) 159(2) 1_565
C17 H17 O21 0.93(3) 2.41(3) 3.303(3) 161(2) 2_766
C24 H24 Cl2 0.98(2) 2.78(3) 3.725(3) 161.2(19) 1_565
C25 H25 Cl3 0.96(3) 3.00(3) 3.945(2) 170.6(19) 1_565
C211 H213 Cl3 0.949(16) 3.03(3) 3.589(4) 119(2) 1_565

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ni6mq
_database_code_depnum_ccdc_archive 'CCDC 1814016'
_audit_update_record             
;
2017-12-29 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_date             2017-12-28T14:27:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'Ni1, Cl2, (C10 H9 N1 O1)2'
_chemical_formula_sum            'C20 H18 Cl2 N2 Ni O2'
_chemical_formula_weight         447.97

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.3725(4)
_cell_length_b                   15.1031(6)
_cell_length_c                   12.5383(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.770(3)
_cell_angle_gamma                90
_cell_volume                     1963.27(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2710
_cell_measurement_theta_min      3.2445
_cell_measurement_theta_max      29.1137

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       fragment
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.503
_exptl_crystal_size_mid          0.227
_exptl_crystal_size_min          0.190
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_F_000             920

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.90687
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.0604
_diffrn_orient_matrix_ub_11      -0.0382096
_diffrn_orient_matrix_ub_12      0.0347894
_diffrn_orient_matrix_ub_13      0.0201453
_diffrn_orient_matrix_ub_21      0.0479898
_diffrn_orient_matrix_ub_22      0.0310568
_diffrn_orient_matrix_ub_23      -0.0137234
_diffrn_orient_matrix_ub_31      -0.0302697
_diffrn_orient_matrix_ub_32      0.0053539
_diffrn_orient_matrix_ub_33      -0.0511194
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_number            9827
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.251
_diffrn_reflns_theta_max         29.178
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.853
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.853
_reflns_Friedel_coverage         0
_reflns_number_total             4529
_reflns_number_gt                3447
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0313P)²+0.5921P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4529
_refine_ls_number_parameters     316
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.056
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0861
_refine_ls_wR_factor_gt          0.0754
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.054

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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_
_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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.79968(3) 0.09014(2) 0.69988(2) 0.03940(10) Uani 1 1 d . . . . .
Cl1 Cl 0.89469(7) 0.12327(5) 0.54668(5) 0.05432(18) Uani 1 1 d . . . . .
Cl2 Cl 0.74401(7) 0.19894(5) 0.81035(6) 0.06052(19) Uani 1 1 d . . . . .
N11 N 0.91026(16) -0.00171(12) 0.77643(13) 0.0351(4) Uani 1 1 d . . . . .
C28 C 0.7429(2) -0.08852(16) 0.55761(17) 0.0383(5) Uani 1 1 d . . . . .
N21 N 0.63664(16) 0.01978(12) 0.66792(13) 0.0355(4) Uani 1 1 d . . . . .
C210 C 0.5130(2) -0.09915(16) 0.58348(17) 0.0382(5) Uani 1 1 d . . . . .
C19 C 0.88335(19) -0.03838(14) 0.87422(16) 0.0334(5) Uani 1 1 d . . . . .
C110 C 0.9626(2) -0.10503(15) 0.92040(17) 0.0357(5) Uani 1 1 d . . . . .
C18 C 0.7755(2) -0.00949(17) 0.93076(18) 0.0409(5) Uani 1 1 d . . . . .
C29 C 0.6312(2) -0.05498(15) 0.60486(16) 0.0337(5) Uani 1 1 d . . . . .
C16 C 0.8280(2) -0.11316(17) 1.07227(18) 0.0445(6) Uani 1 1 d . . . . .
C12 C 1.0121(2) -0.03202(17) 0.72643(18) 0.0409(5) Uani 1 1 d . . . . .
O11 O 0.78716(19) -0.14456(14) 1.16750(13) 0.0607(5) Uani 1 1 d . . . . .
C22 C 0.5279(2) 0.04965(19) 0.70717(18) 0.0432(6) Uani 1 1 d . . . . .
C24 C 0.4009(2) -0.0640(2) 0.62662(18) 0.0473(6) Uani 1 1 d . . . . .
C15 C 0.9333(2) -0.14140(17) 1.02075(18) 0.0410(5) Uani 1 1 d . . . . .
C17 C 0.7491(2) -0.04608(18) 1.02651(19) 0.0468(6) Uani 1 1 d . . . . .
C14 C 1.0679(2) -0.13519(18) 0.8618(2) 0.0453(6) Uani 1 1 d . . . . .
C25 C 0.5096(3) -0.17533(17) 0.51830(19) 0.0464(6) Uani 1 1 d . . . . .
C27 C 0.7368(2) -0.16135(18) 0.49453(19) 0.0448(6) Uani 1 1 d . . . . .
O21 O 0.62773(19) -0.27692(13) 0.40813(15) 0.0659(5) Uani 1 1 d . . . . .
C13 C 1.0915(2) -0.09890(18) 0.7660(2) 0.0481(6) Uani 1 1 d . . . . .
C26 C 0.6188(3) -0.20565(17) 0.47415(18) 0.0468(6) Uani 1 1 d . . . . .
C23 C 0.4082(2) 0.0095(2) 0.68792(19) 0.0484(6) Uani 1 1 d . . . . .
C111 C 0.8624(3) -0.2127(2) 1.2178(2) 0.0632(8) Uani 1 1 d D . . . .
C211 C 0.5121(4) -0.3251(3) 0.3842(4) 0.0894(12) Uani 1 1 d D . . . .
H24 H 0.320(2) -0.0935(15) 0.6083(17) 0.041(6) Uiso 1 1 d . . . . .
H15 H 0.989(2) -0.1837(18) 1.0475(18) 0.049(7) Uiso 1 1 d . . . . .
H28 H 0.822(2) -0.0575(16) 0.5665(17) 0.043(6) Uiso 1 1 d . . . . .
H22 H 0.536(2) 0.1000(16) 0.7461(18) 0.038(6) Uiso 1 1 d . . . . .
H23 H 0.337(2) 0.0369(18) 0.7168(18) 0.051(7) Uiso 1 1 d . . . . .
H18 H 0.725(2) 0.0345(17) 0.9015(17) 0.045(7) Uiso 1 1 d . . . . .
H14 H 1.115(2) -0.1774(17) 0.8907(18) 0.043(7) Uiso 1 1 d . . . . .
H12 H 1.029(2) -0.0053(16) 0.6629(18) 0.045(7) Uiso 1 1 d . . . . .
H27 H 0.813(2) -0.1867(18) 0.4623(19) 0.058(8) Uiso 1 1 d . . . . .
H13 H 1.162(3) -0.1194(18) 0.7260(19) 0.057(8) Uiso 1 1 d . . . . .
H25 H 0.432(3) -0.2026(19) 0.509(2) 0.060(8) Uiso 1 1 d . . . . .
H17 H 0.678(2) -0.0270(18) 1.0627(19) 0.058(8) Uiso 1 1 d . . . . .
H111 H 0.876(2) -0.2640(15) 1.1718(18) 0.079(10) Uiso 1 1 d D . . . .
H112 H 0.9432(19) -0.1909(19) 1.246(2) 0.089(11) Uiso 1 1 d D . . . .
H113 H 0.809(2) -0.233(2) 1.2741(18) 0.106(12) Uiso 1 1 d D . . . .
H211 H 0.535(3) -0.3743(17) 0.341(2) 0.110(13) Uiso 1 1 d D . . . .
H212 H 0.447(3) -0.2880(17) 0.349(2) 0.094(11) Uiso 1 1 d D . . . .
H213 H 0.476(3) -0.347(2) 0.4500(16) 0.092(13) Uiso 1 1 d D . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N11 2.0232(18) . ?
Ni1 N21 2.0268(18) . ?
Ni1 Cl2 2.2363(7) . ?
Ni1 Cl1 2.2424(7) . ?
N11 C12 1.327(3) . ?
N11 C19 1.382(3) . ?
C28 C27 1.355(3) . ?
C28 C29 1.412(3) . ?
C28 H28 0.95(2) . ?
N21 C22 1.323(3) . ?
N21 C29 1.379(3) . ?
C210 C24 1.402(3) . ?
C210 C25 1.411(3) . ?
C210 C29 1.414(3) . ?
C19 C18 1.412(3) . ?
C19 C110 1.412(3) . ?
C110 C14 1.410(3) . ?
C110 C15 1.414(3) . ?
C18 C17 1.357(3) . ?
C18 H18 0.92(2) . ?
C16 C15 1.355(3) . ?
C16 O11 1.364(3) . ?
C16 C17 1.413(4) . ?
C12 C13 1.385(3) . ?
C12 H12 0.92(2) . ?
O11 C111 1.426(3) . ?
C22 C23 1.396(3) . ?
C22 H22 0.91(2) . ?
C24 C23 1.351(4) . ?
C24 H24 0.97(2) . ?
C15 H15 0.92(3) . ?
C17 H17 0.92(3) . ?
C14 C13 1.349(3) . ?
C14 H14 0.88(2) . ?
C25 C26 1.356(4) . ?
C25 H25 0.91(3) . ?
C27 C26 1.411(3) . ?
C27 H27 0.98(3) . ?
O21 C26 1.363(3) . ?
O21 C211 1.426(4) . ?
C13 H13 0.95(3) . ?
C23 H23 0.93(3) . ?
C111 H111 0.979(15) . ?
C111 H112 0.956(15) . ?
C111 H113 0.961(16) . ?
C211 H211 0.955(16) . ?
C211 H212 0.971(16) . ?
C211 H213 0.973(16) . ?

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
_geom_angle_publ_flag
N11 Ni1 N21 101.05(7) . . ?
N11 Ni1 Cl2 111.31(5) . . ?
N21 Ni1 Cl2 106.13(6) . . ?
N11 Ni1 Cl1 107.56(5) . . ?
N21 Ni1 Cl1 109.49(5) . . ?
Cl2 Ni1 Cl1 119.69(3) . . ?
C12 N11 C19 117.82(19) . . ?
C12 N11 Ni1 117.42(15) . . ?
C19 N11 Ni1 124.66(14) . . ?
C27 C28 C29 120.8(2) . . ?
C27 C28 H28 119.5(14) . . ?
C29 C28 H28 119.5(15) . . ?
C22 N21 C29 118.2(2) . . ?
C22 N21 Ni1 117.58(17) . . ?
C29 N21 Ni1 124.21(14) . . ?
C24 C210 C25 121.7(2) . . ?
C24 C210 C29 118.2(2) . . ?
C25 C210 C29 120.1(2) . . ?
N11 C19 C18 120.4(2) . . ?
N11 C19 C110 121.24(19) . . ?
C18 C19 C110 118.3(2) . . ?
C14 C110 C19 117.8(2) . . ?
C14 C110 C15 121.9(2) . . ?
C19 C110 C15 120.2(2) . . ?
C17 C18 C19 120.2(2) . . ?
C17 C18 H18 121.2(15) . . ?
C19 C18 H18 118.6(15) . . ?
N21 C29 C28 121.0(2) . . ?
N21 C29 C210 121.0(2) . . ?
C28 C29 C210 118.0(2) . . ?
C15 C16 O11 125.8(2) . . ?
C15 C16 C17 119.8(2) . . ?
O11 C16 C17 114.4(2) . . ?
N11 C12 C13 123.7(2) . . ?
N11 C12 H12 116.1(15) . . ?
C13 C12 H12 120.2(15) . . ?
C16 O11 C111 117.2(2) . . ?
N21 C22 C23 123.5(3) . . ?
N21 C22 H22 115.2(15) . . ?
C23 C22 H22 121.3(15) . . ?
C23 C24 C210 119.9(2) . . ?
C23 C24 H24 123.1(14) . . ?
C210 C24 H24 117.0(14) . . ?
C16 C15 C110 120.0(2) . . ?
C16 C15 H15 123.4(15) . . ?
C110 C15 H15 116.6(15) . . ?
C18 C17 C16 121.4(2) . . ?
C18 C17 H17 119.6(16) . . ?
C16 C17 H17 119.0(16) . . ?
C13 C14 C110 119.8(2) . . ?
C13 C14 H14 123.2(16) . . ?
C110 C14 H14 117.0(16) . . ?
C26 C25 C210 120.4(2) . . ?
C26 C25 H25 122.8(17) . . ?
C210 C25 H25 116.8(17) . . ?
C28 C27 C26 121.0(2) . . ?
C28 C27 H27 122.3(15) . . ?
C26 C27 H27 116.7(15) . . ?
C26 O21 C211 117.3(3) . . ?
C14 C13 C12 119.5(2) . . ?
C14 C13 H13 120.0(16) . . ?
C12 C13 H13 120.4(16) . . ?
C25 C26 O21 126.0(2) . . ?
C25 C26 C27 119.8(2) . . ?
O21 C26 C27 114.2(2) . . ?
C24 C23 C22 119.3(2) . . ?
C24 C23 H23 123.8(16) . . ?
C22 C23 H23 116.9(16) . . ?
O11 C111 H111 113.6(16) . . ?
O11 C111 H112 112.0(19) . . ?
H111 C111 H112 110.1(19) . . ?
O11 C111 H113 104(2) . . ?
H111 C111 H113 106.1(19) . . ?
H112 C111 H113 111.1(19) . . ?
O21 C211 H211 107(2) . . ?
O21 C211 H212 111.7(19) . . ?
H211 C211 H212 112(2) . . ?
O21 C211 H213 110(2) . . ?
H211 C211 H213 109(2) . . ?
H212 C211 H213 108(2) . . ?

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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N11 C19 C18 -179.4(2) . . . . ?
Ni1 N11 C19 C18 -3.0(3) . . . . ?
C12 N11 C19 C110 0.9(3) . . . . ?
Ni1 N11 C19 C110 177.27(14) . . . . ?
N11 C19 C110 C14 -2.1(3) . . . . ?
C18 C19 C110 C14 178.2(2) . . . . ?
N11 C19 C110 C15 179.81(19) . . . . ?
C18 C19 C110 C15 0.1(3) . . . . ?
N11 C19 C18 C17 179.6(2) . . . . ?
C110 C19 C18 C17 -0.7(3) . . . . ?
C22 N21 C29 C28 177.8(2) . . . . ?
Ni1 N21 C29 C28 0.4(3) . . . . ?
C22 N21 C29 C210 -0.6(3) . . . . ?
Ni1 N21 C29 C210 -178.08(14) . . . . ?
C27 C28 C29 N21 -179.1(2) . . . . ?
C27 C28 C29 C210 -0.6(3) . . . . ?
C24 C210 C29 N21 1.1(3) . . . . ?
C25 C210 C29 N21 179.70(19) . . . . ?
C24 C210 C29 C28 -177.4(2) . . . . ?
C25 C210 C29 C28 1.2(3) . . . . ?
C19 N11 C12 C13 0.9(3) . . . . ?
Ni1 N11 C12 C13 -175.69(19) . . . . ?
C15 C16 O11 C111 0.5(4) . . . . ?
C17 C16 O11 C111 179.8(2) . . . . ?
C29 N21 C22 C23 -0.1(3) . . . . ?
Ni1 N21 C22 C23 177.51(18) . . . . ?
C25 C210 C24 C23 -179.4(2) . . . . ?
C29 C210 C24 C23 -0.9(3) . . . . ?
O11 C16 C15 C110 178.0(2) . . . . ?
C17 C16 C15 C110 -1.3(4) . . . . ?
C14 C110 C15 C16 -177.1(2) . . . . ?
C19 C110 C15 C16 0.9(3) . . . . ?
C19 C18 C17 C16 0.3(4) . . . . ?
C15 C16 C17 C18 0.7(4) . . . . ?
O11 C16 C17 C18 -178.6(2) . . . . ?
C19 C110 C14 C13 1.5(3) . . . . ?
C15 C110 C14 C13 179.5(2) . . . . ?
C24 C210 C25 C26 177.3(2) . . . . ?
C29 C210 C25 C26 -1.3(3) . . . . ?
C29 C28 C27 C26 0.1(4) . . . . ?
C110 C14 C13 C12 0.3(4) . . . . ?
N11 C12 C13 C14 -1.5(4) . . . . ?
C210 C25 C26 O21 -178.4(2) . . . . ?
C210 C25 C26 C27 0.7(4) . . . . ?
C211 O21 C26 C25 -1.0(4) . . . . ?
C211 O21 C26 C27 179.9(3) . . . . ?
C28 C27 C26 C25 -0.1(4) . . . . ?
C28 C27 C26 O21 179.1(2) . . . . ?
C210 C24 C23 C22 0.2(4) . . . . ?
N21 C22 C23 C24 0.3(4) . . . . ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ag6mq
_database_code_depnum_ccdc_archive 'CCDC 1814015'
_audit_update_record             
;
2017-12-29 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_date             2017-12-29T10:00:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
_chemical_formula_moiety         'Ag1, (N1 O3), (C10 H9 N1 O1)2'
_chemical_formula_sum            'C20 H18 Ag N3 O5'
_chemical_formula_weight         488.24

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.3869(2)
_cell_length_b                   15.0294(5)
_cell_length_c                   17.1175(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.470(3)
_cell_angle_gamma                90
_cell_volume                     1879.67(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2493
_cell_measurement_theta_min      3.9297
_cell_measurement_theta_max      73.2374

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.372
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.043
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_F_000             984

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    8.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.6405
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.136
_shelx_estimated_absorpt_T_max   0.7

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.0604
_diffrn_orient_matrix_ub_11      0.0831785
_diffrn_orient_matrix_ub_12      0.0674759
_diffrn_orient_matrix_ub_13      0.0630027
_diffrn_orient_matrix_ub_21      0.0338248
_diffrn_orient_matrix_ub_22      0.0654029
_diffrn_orient_matrix_ub_23      -0.0656338
_diffrn_orient_matrix_ub_31      -0.1908287
_diffrn_orient_matrix_ub_32      0.0409206
_diffrn_orient_matrix_ub_33      0.0009829
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_number            7973
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.933
_diffrn_reflns_theta_max         73.397
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.972
_reflns_Friedel_coverage         0
_reflns_number_total             3681
_reflns_number_gt                2951
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0448P)²+7.1572P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.00029(7)
_refine_ls_number_reflns         3681
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1535
_refine_ls_wR_factor_gt          0.1461
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.034
_refine_diff_density_min         -0.914
_refine_diff_density_rms         0.092

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
Ag Ag 0.1306 4.282 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag1 Ag 0.21873(8) 0.97089(4) 0.02623(3) 0.0645(2) Uani 1 1 d . . . . .
N11 N 0.2908(7) 0.8951(4) -0.0723(3) 0.0479(12) Uani 1 1 d . . . . .
C12 C 0.2628(9) 0.8075(5) -0.0758(4) 0.0546(16) Uani 1 1 d . . . . .
H12 H 0.2275 0.7793 -0.032 0.066 Uiso 1 1 calc R U . . .
C13 C 0.2835(9) 0.7563(4) -0.1410(4) 0.0530(15) Uani 1 1 d . . . . .
H13 H 0.2657 0.6951 -0.1401 0.064 Uiso 1 1 calc R U . . .
C14 C 0.3300(9) 0.7960(4) -0.2065(4) 0.0475(14) Uani 1 1 d . . . . .
H14 H 0.3404 0.7622 -0.2511 0.057 Uiso 1 1 calc R U . . .
C15 C 0.4098(8) 0.9333(4) -0.2728(3) 0.0417(13) Uani 1 1 d . . . . .
H15 H 0.4218 0.9017 -0.3185 0.05 Uiso 1 1 calc R U . . .
C16 C 0.4384(8) 1.0234(4) -0.2702(4) 0.0463(14) Uani 1 1 d . . . . .
C17 C 0.4209(9) 1.0705(4) -0.2008(4) 0.0506(15) Uani 1 1 d . . . . .
H17 H 0.4427 1.1315 -0.1989 0.061 Uiso 1 1 calc R U . . .
C18 C 0.3731(9) 1.0294(4) -0.1365(4) 0.0510(15) Uani 1 1 d . . . . .
H18 H 0.3609 1.0624 -0.0916 0.061 Uiso 1 1 calc R U . . .
C19 C 0.3417(8) 0.9366(4) -0.1373(3) 0.0410(12) Uani 1 1 d . . . . .
C110 C 0.3625(8) 0.8883(4) -0.2066(3) 0.0402(12) Uani 1 1 d . . . . .
C111 C 0.4790(12) 1.0307(5) -0.4055(4) 0.0640(19) Uani 1 1 d . . . . .
H11A H 0.51 1.0732 -0.4433 0.096 Uiso 1 1 calc R U . . .
H11B H 0.5672 0.9834 -0.4 0.096 Uiso 1 1 calc R U . . .
H11C H 0.3595 1.0068 -0.4234 0.096 Uiso 1 1 calc R U . . .
O1 O 0.4793(7) 1.0734(3) -0.3309(3) 0.0562(11) Uani 1 1 d . . . . .
N21 N 0.1813(7) 1.0835(4) 0.0997(3) 0.0508(13) Uani 1 1 d . . . . .
C22 C 0.2231(9) 1.1640(5) 0.0737(4) 0.0564(17) Uani 1 1 d . . . . .
H22 H 0.2484 1.169 0.0222 0.068 Uiso 1 1 calc R U . . .
C23 C 0.2306(10) 1.2402(5) 0.1199(4) 0.0605(18) Uani 1 1 d . . . . .
H23 H 0.2604 1.2946 0.0992 0.073 Uiso 1 1 calc R U . . .
C24 C 0.1941(9) 1.2353(4) 0.1959(4) 0.0529(15) Uani 1 1 d . . . . .
H24 H 0.199 1.286 0.2273 0.064 Uiso 1 1 calc R U . . .
C25 C 0.1068(9) 1.1421(4) 0.3033(4) 0.0491(14) Uani 1 1 d . . . . .
H25 H 0.112 1.191 0.3368 0.059 Uiso 1 1 calc R U . . .
C26 C 0.0585(9) 1.0605(5) 0.3289(4) 0.0502(15) Uani 1 1 d . . . . .
C27 C 0.0532(9) 0.9863(4) 0.2782(4) 0.0512(15) Uani 1 1 d . . . . .
H27 H 0.0215 0.931 0.2964 0.061 Uiso 1 1 calc R U . . .
C28 C 0.0931(9) 0.9936(4) 0.2040(4) 0.0513(15) Uani 1 1 d . . . . .
H28 H 0.088 0.9438 0.1715 0.062 Uiso 1 1 calc R U . . .
C29 C 0.1424(8) 1.0770(4) 0.1759(3) 0.0465(14) Uani 1 1 d . . . . .
C210 C 0.1489(8) 1.1521(4) 0.2256(4) 0.0450(13) Uani 1 1 d . . . . .
C211 C 0.0070(13) 1.1174(6) 0.4533(4) 0.078(2) Uani 1 1 d . . . . .
H21A H -0.025 1.0972 0.5026 0.117 Uiso 1 1 calc R U . . .
H21B H 0.1244 1.1461 0.4624 0.117 Uiso 1 1 calc R U . . .
H21C H -0.0835 1.1589 0.4295 0.117 Uiso 1 1 calc R U . . .
O2 O 0.0147(8) 1.0433(3) 0.4018(3) 0.0653(13) Uani 1 1 d . . . . .
N3 N -0.0223(9) 1.2326(4) -0.0923(3) 0.0602(15) Uani 1 1 d . . . . .
O3 O -0.1670(9) 1.1869(4) -0.0979(3) 0.0744(15) Uani 1 1 d . . . . .
O4 O 0.1126(10) 1.2049(5) -0.1186(4) 0.100(2) Uani 1 1 d . . . . .
O5 O -0.0202(9) 1.3053(4) -0.0590(3) 0.0814(16) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ag1 N21 2.151(5) . ?
Ag1 N11 2.165(5) . ?
Ag1 Ag1 3.3406(12) 3_575 ?
N11 C12 1.334(8) . ?
N11 C19 1.375(7) . ?
C12 C13 1.383(9) . ?
C12 H12 0.93 . ?
C13 C14 1.357(8) . ?
C13 H13 0.93 . ?
C14 C110 1.408(8) . ?
C14 H14 0.93 . ?
C15 C16 1.370(8) . ?
C15 C110 1.407(8) . ?
C15 H15 0.93 . ?
C16 O1 1.353(7) . ?
C16 C17 1.406(9) . ?
C17 C18 1.353(9) . ?
C17 H17 0.93 . ?
C18 C19 1.414(8) . ?
C18 H18 0.93 . ?
C19 C110 1.418(8) . ?
C111 O1 1.430(8) . ?
C111 H11A 0.96 . ?
C111 H11B 0.96 . ?
C111 H11C 0.96 . ?
N21 C22 1.340(9) . ?
N21 C29 1.380(8) . ?
C22 C23 1.388(10) . ?
C22 H22 0.93 . ?
C23 C24 1.369(9) . ?
C23 H23 0.93 . ?
C24 C210 1.408(9) . ?
C24 H24 0.93 . ?
C25 C26 1.367(9) . ?
C25 C210 1.417(8) . ?
C25 H25 0.93 . ?
C26 O2 1.360(7) . ?
C26 C27 1.409(9) . ?
C27 C28 1.351(9) . ?
C27 H27 0.93 . ?
C28 C29 1.409(9) . ?
C28 H28 0.93 . ?
C29 C210 1.411(9) . ?
C211 O2 1.426(9) . ?
C211 H21A 0.96 . ?
C211 H21B 0.96 . ?
C211 H21C 0.96 . ?
N3 O4 1.226(8) . ?
N3 O5 1.230(8) . ?
N3 O3 1.263(8) . ?

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
_geom_angle_publ_flag
N21 Ag1 N11 159.5(2) . . ?
N21 Ag1 Ag1 75.43(14) . 3_575 ?
N11 Ag1 Ag1 105.50(14) . 3_575 ?
C12 N11 C19 118.1(5) . . ?
C12 N11 Ag1 120.0(4) . . ?
C19 N11 Ag1 121.3(4) . . ?
N11 C12 C13 123.4(6) . . ?
N11 C12 H12 118.3 . . ?
C13 C12 H12 118.3 . . ?
C14 C13 C12 119.6(6) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C110 119.9(6) . . ?
C13 C14 H14 120.1 . . ?
C110 C14 H14 120.1 . . ?
C16 C15 C110 120.3(5) . . ?
C16 C15 H15 119.8 . . ?
C110 C15 H15 119.8 . . ?
O1 C16 C15 125.1(6) . . ?
O1 C16 C17 115.4(5) . . ?
C15 C16 C17 119.5(6) . . ?
C18 C17 C16 121.6(6) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 120.3(6) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
N11 C19 C18 120.2(5) . . ?
N11 C19 C110 121.4(5) . . ?
C18 C19 C110 118.4(5) . . ?
C15 C110 C14 122.5(5) . . ?
C15 C110 C19 119.8(5) . . ?
C14 C110 C19 117.7(5) . . ?
O1 C111 H11A 109.5 . . ?
O1 C111 H11B 109.5 . . ?
H11A C111 H11B 109.5 . . ?
O1 C111 H11C 109.5 . . ?
H11A C111 H11C 109.5 . . ?
H11B C111 H11C 109.5 . . ?
C16 O1 C111 117.8(5) . . ?
C22 N21 C29 117.9(6) . . ?
C22 N21 Ag1 117.4(4) . . ?
C29 N21 Ag1 124.0(4) . . ?
N21 C22 C23 123.2(6) . . ?
N21 C22 H22 118.4 . . ?
C23 C22 H22 118.4 . . ?
C24 C23 C22 120.0(6) . . ?
C24 C23 H23 120 . . ?
C22 C23 H23 120 . . ?
C23 C24 C210 118.8(6) . . ?
C23 C24 H24 120.6 . . ?
C210 C24 H24 120.6 . . ?
C26 C25 C210 120.0(6) . . ?
C26 C25 H25 120 . . ?
C210 C25 H25 120 . . ?
O2 C26 C25 125.0(6) . . ?
O2 C26 C27 115.2(6) . . ?
C25 C26 C27 119.8(6) . . ?
C28 C27 C26 121.6(6) . . ?
C28 C27 H27 119.2 . . ?
C26 C27 H27 119.2 . . ?
C27 C28 C29 119.8(6) . . ?
C27 C28 H28 120.1 . . ?
C29 C28 H28 120.1 . . ?
N21 C29 C28 119.1(6) . . ?
N21 C29 C210 121.3(6) . . ?
C28 C29 C210 119.6(6) . . ?
C24 C210 C29 118.8(6) . . ?
C24 C210 C25 122.0(6) . . ?
C29 C210 C25 119.2(6) . . ?
O2 C211 H21A 109.5 . . ?
O2 C211 H21B 109.5 . . ?
H21A C211 H21B 109.5 . . ?
O2 C211 H21C 109.5 . . ?
H21A C211 H21C 109.5 . . ?
H21B C211 H21C 109.5 . . ?
C26 O2 C211 117.1(6) . . ?
O4 N3 O5 121.1(8) . . ?
O4 N3 O3 120.8(7) . . ?
O5 N3 O3 118.1(6) . . ?

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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C19 N11 C12 C13 0.4(10) . . . . ?
Ag1 N11 C12 C13 171.7(5) . . . . ?
N11 C12 C13 C14 -1.8(11) . . . . ?
C12 C13 C14 C110 2.0(10) . . . . ?
C110 C15 C16 O1 -178.1(6) . . . . ?
C110 C15 C16 C17 0.3(9) . . . . ?
O1 C16 C17 C18 177.3(6) . . . . ?
C15 C16 C17 C18 -1.2(10) . . . . ?
C16 C17 C18 C19 0.9(10) . . . . ?
C12 N11 C19 C18 -180.0(6) . . . . ?
Ag1 N11 C19 C18 8.9(8) . . . . ?
C12 N11 C19 C110 0.7(9) . . . . ?
Ag1 N11 C19 C110 -170.5(4) . . . . ?
C17 C18 C19 N11 -179.1(6) . . . . ?
C17 C18 C19 C110 0.3(9) . . . . ?
C16 C15 C110 C14 179.4(6) . . . . ?
C16 C15 C110 C19 0.9(9) . . . . ?
C13 C14 C110 C15 -179.5(6) . . . . ?
C13 C14 C110 C19 -1.0(9) . . . . ?
N11 C19 C110 C15 178.2(5) . . . . ?
C18 C19 C110 C15 -1.2(9) . . . . ?
N11 C19 C110 C14 -0.4(9) . . . . ?
C18 C19 C110 C14 -179.8(6) . . . . ?
C15 C16 O1 C111 5.2(10) . . . . ?
C17 C16 O1 C111 -173.3(6) . . . . ?
C29 N21 C22 C23 0.6(10) . . . . ?
Ag1 N21 C22 C23 -170.4(5) . . . . ?
N21 C22 C23 C24 -0.1(11) . . . . ?
C22 C23 C24 C210 -0.1(10) . . . . ?
C210 C25 C26 O2 -179.7(6) . . . . ?
C210 C25 C26 C27 0.9(10) . . . . ?
O2 C26 C27 C28 179.8(6) . . . . ?
C25 C26 C27 C28 -0.7(11) . . . . ?
C26 C27 C28 C29 0.4(10) . . . . ?
C22 N21 C29 C28 178.3(6) . . . . ?
Ag1 N21 C29 C28 -11.4(8) . . . . ?
C22 N21 C29 C210 -0.9(9) . . . . ?
Ag1 N21 C29 C210 169.5(4) . . . . ?
C27 C28 C29 N21 -179.5(6) . . . . ?
C27 C28 C29 C210 -0.3(10) . . . . ?
C23 C24 C210 C29 -0.2(9) . . . . ?
C23 C24 C210 C25 -179.1(6) . . . . ?
N21 C29 C210 C24 0.7(9) . . . . ?
C28 C29 C210 C24 -178.4(6) . . . . ?
N21 C29 C210 C25 179.6(6) . . . . ?
C28 C29 C210 C25 0.5(9) . . . . ?
C26 C25 C210 C24 178.1(6) . . . . ?
C26 C25 C210 C29 -0.8(9) . . . . ?
C25 C26 O2 C211 4.4(10) . . . . ?
C27 C26 O2 C211 -176.1(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12 O3 0.93 2.39 3.157(8) 140 3_575
C13 H13 O1 0.93 2.57 3.359(8) 142.9 2_544
C22 H22 O4 0.93 2.53 3.330(9) 144.4 .
C25 H25 O3 0.93 2.6 3.380(9) 142.2 4_686
C28 H28 O3 0.93 2.45 3.353(9) 164 3_575
C12 H12 O3 0.93 2.39 3.157(8) 140 3_575
C13 H13 O1 0.93 2.57 3.359(8) 142.9 2_544
C22 H22 O4 0.93 2.53 3.330(9) 144.4 .
C25 H25 O3 0.93 2.6 3.380(9) 142.2 4_686
C28 H28 O3 0.93 2.45 3.353(9) 164 3_575

