# Electronic Supplementary Material (ESI) for Sustainable Energy & Fuels.
# This journal is © The Royal Society of Chemistry 2020
#######################################################################
#
# 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_nq373c
_database_code_depnum_ccdc_archive 'CCDC 1970564'
loop_
_audit_author_name
_audit_author_address
'Jacques Pecaut'
;Univ Grenoble Alpes, CEA, CNRS, IRIG, SYMMES
France
;
_audit_update_record
;
2019-12-06 deposited with the CCDC. 2020-05-11 downloaded from the CCDC.
;
_audit_creation_method SHELXL-2013
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C20 H16 Cl2 Co N6'
_chemical_formula_weight 470.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 21/c'
_space_group_name_Hall '-P 2ybc'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 15.4767(3)
_cell_length_b 14.4574(2)
_cell_length_c 8.89585(14)
_cell_angle_alpha 90
_cell_angle_beta 100.3316(15)
_cell_angle_gamma 90
_cell_volume 1958.20(6)
_cell_formula_units_Z 4
_cell_measurement_temperature 150(2)
_cell_measurement_reflns_used 8516
_cell_measurement_theta_min 2.6680
_cell_measurement_theta_max 32.2130
_exptl_crystal_description irregular
_exptl_crystal_colour 'translucent intense orange'
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_density_diffrn 1.595
_exptl_crystal_F_000 956
_exptl_transmission_factor_min ?
_exptl_transmission_factor_max ?
_exptl_crystal_size_max 0.243
_exptl_crystal_size_mid 0.138
_exptl_crystal_size_min 0.129
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 1 0 0.0561 -0.0000 1.0000 -0.0000 0.0296 -0.0202 -0.0335
0 -1 0 0.0821 0.0000 -1.0000 0.0000 -0.0296 0.0202 0.0335
1 -2 -2 0.0509 1.0000 -2.0000 -2.0000 -0.0544 -0.0949 0.1530
-2 1 0 0.0896 -2.0000 1.0000 0.0000 -0.0444 -0.0435 -0.0850
1 2 2 0.0939 1.0000 2.0000 2.0000 0.1284 0.1183 -0.1015
2 0 1 0.1213 2.0000 -0.0000 1.0000 0.0901 0.0968 0.0214
1 -1 0 0.1089 1.0000 -1.0000 0.0000 0.0074 0.0319 0.0592
2 0 -1 0.0354 2.0000 -0.0000 -1.0000 0.0580 -0.0502 0.0817
-2 0 1 0.0934 -2.0000 0.0000 1.0000 -0.0580 0.0502 -0.0817
-2 -1 0 0.0962 -2.0000 -1.0000 0.0000 -0.1037 -0.0031 -0.0181
0 0 1 0.0857 -0.0000 0.0000 1.0000 0.0161 0.0735 -0.0302
_exptl_absorpt_coefficient_mu 1.169
_shelx_estimated_absorpt_T_min 0.764
_shelx_estimated_absorpt_T_max 0.864
_exptl_absorpt_correction_type analytical
_exptl_absorpt_correction_T_min 0.994
_exptl_absorpt_correction_T_max 0.996
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec 9 2014,15:38:47)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 150(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_source 'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type 'Xcalibur, Sapphire3'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean 15.9653
_diffrn_reflns_number 23481
_diffrn_reflns_av_unetI/netI 0.0278
_diffrn_reflns_av_R_equivalents 0.0289
_diffrn_reflns_limit_h_min -22
_diffrn_reflns_limit_h_max 21
_diffrn_reflns_limit_k_min -20
_diffrn_reflns_limit_k_max 20
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 1.942
_diffrn_reflns_theta_max 30.507
_diffrn_reflns_theta_full 25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total 5983
_reflns_number_gt 5015
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_max .
_reflns_Friedel_fraction_full .
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_computing_data_collection
;
Agilent Technologies, (2014), CrysAlisPro Software system,
version 1.171.37.35, Agilent Technologies UK Ltd, Oxford, UK
;
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
1 omega 4.00 94.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 25.5614 57.0000 60.0000 90
#__ type_ start__ end____ width___ exp.time_
2 omega 4.00 94.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 25.5614 57.0000 150.0000 90
#__ type_ start__ end____ width___ exp.time_
3 omega -47.00 51.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 25.5614 -37.0000 150.0000 98
#__ type_ start__ end____ width___ exp.time_
4 omega -25.00 67.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 25.5614 -99.0000 -60.0000 92
#__ type_ start__ end____ width___ exp.time_
5 omega 35.00 60.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 25.5614 178.0000 150.0000 25
#__ type_ start__ end____ width___ exp.time_
6 omega -4.00 95.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 25.5614 76.0000 -99.0000 99
;
_computing_cell_refinement
;
Agilent Technologies, (2014), CrysAlisPro Software system,
version 1.171. 37.35, Agilent Technologies UK Ltd, Oxford, UK
;
_computing_data_reduction
;
Agilent Technologies, (2014), CrysAlisPro Software system,
version 1.171. 37.35, Agilent Technologies UK Ltd, Oxford, UK
;
_computing_structure_solution
;
SUPERFLIP program (Palatinus, L. & Chapuis, G. J. Appl. Cryst., 2007,
40, 786-790)
;
_computing_structure_refinement
;
OLEX2: a complete structure solution, refinement and analysis program
(O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and
H. Puschmann. J. Appl. Cryst. 2009, 42, 339-34).
;
_computing_molecular_graphics
;
Mercury 3.1 New software for searching the Cambridge Structural Database
and visualizing crystal structures (I.J. Bruno, J.C. Cole, P.R. Edgington,
M. Kessler, C.F. Macrae, P. McCabe, J. Pearson, R. Taylor,
Acta Cryst., 2002, B58, 389-397)
;
_computing_publication_material
;
SHELXL-2013
(Sheldrick, Acta Cryst. A64, 112-122)
;
_refine_special_details
;
?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0254P)^2^+1.1223P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
_atom_sites_solution_hydrogens difmap
_refine_ls_hydrogen_treatment refall
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_number_reflns 5983
_refine_ls_number_parameters 326
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0418
_refine_ls_R_factor_gt 0.0310
_refine_ls_wR_factor_ref 0.0697
_refine_ls_wR_factor_gt 0.0660
_refine_ls_goodness_of_fit_ref 1.031
_refine_ls_restrained_S_all 1.031
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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 0.24987(2) 0.49733(2) 0.50845(2) 0.01416(5) Uani 1 1 d . . . . .
Cl1 Cl 0.13202(2) 0.38959(2) 0.36157(4) 0.01853(8) Uani 1 1 d . . . . .
Cl2 Cl 0.37261(2) 0.58834(3) 0.67385(4) 0.02226(8) Uani 1 1 d . . . . .
N6 N 0.19311(8) 0.49544(9) 0.70373(13) 0.0165(2) Uani 1 1 d . . . . .
N4 N 0.16310(8) 0.60021(8) 0.41746(13) 0.0150(2) Uani 1 1 d . . . . .
N2 N 0.43226(8) 0.44553(9) 0.38694(14) 0.0175(2) Uani 1 1 d . . . . .
N5 N 0.06467(8) 0.57705(9) 0.58870(14) 0.0171(2) Uani 1 1 d . . . . .
N1 N 0.32894(8) 0.38062(8) 0.52317(14) 0.0164(2) Uani 1 1 d . . . . .
N3 N 0.30721(8) 0.54168(8) 0.32826(13) 0.0151(2) Uani 1 1 d . . . . .
C16 C 0.11530(9) 0.53338(10) 0.71281(16) 0.0159(3) Uani 1 1 d . . . . .
C5 C 0.40827(9) 0.37927(10) 0.48327(15) 0.0163(3) Uani 1 1 d . . . . .
C15 C 0.08445(9) 0.61361(9) 0.45626(16) 0.0154(3) Uani 1 1 d . . . . .
C6 C 0.38505(10) 0.51399(10) 0.29976(16) 0.0165(3) Uani 1 1 d . . . . .
C17 C 0.07976(11) 0.53062(12) 0.84749(18) 0.0232(3) Uani 1 1 d . . . . .
C11 C 0.17930(10) 0.63768(10) 0.28499(16) 0.0184(3) Uani 1 1 d . . . . .
C4 C 0.46933(11) 0.30852(12) 0.53278(18) 0.0229(3) Uani 1 1 d . . . . .
C14 C 0.01844(11) 0.66572(11) 0.36394(18) 0.0201(3) Uani 1 1 d . . . . .
C1 C 0.30560(10) 0.30710(11) 0.60146(17) 0.0198(3) Uani 1 1 d . . . . .
C13 C 0.03586(11) 0.70395(11) 0.23152(19) 0.0252(3) Uani 1 1 d . . . . .
C2 C 0.36104(11) 0.23542(11) 0.65143(18) 0.0231(3) Uani 1 1 d . . . . .
C7 C 0.42266(11) 0.55353(12) 0.18181(19) 0.0239(3) Uani 1 1 d . . . . .
C10 C 0.26508(10) 0.61251(10) 0.24516(16) 0.0185(3) Uani 1 1 d . . . . .
C19 C 0.20549(11) 0.44593(12) 0.96525(18) 0.0258(3) Uani 1 1 d . . . . .
C20 C 0.23760(11) 0.45446(12) 0.83219(17) 0.0219(3) Uani 1 1 d . . . . .
C18 C 0.12459(11) 0.48555(12) 0.97307(18) 0.0258(3) Uani 1 1 d . . . . .
C3 C 0.44577(12) 0.23753(12) 0.61856(19) 0.0264(3) Uani 1 1 d . . . . .
C12 C 0.11765(12) 0.69021(12) 0.19043(19) 0.0258(3) Uani 1 1 d . . . . .
C9 C 0.30016(12) 0.65648(12) 0.13185(19) 0.0270(3) Uani 1 1 d . . . . .
C8 C 0.37941(12) 0.62454(13) 0.0987(2) 0.0290(4) Uani 1 1 d . . . . .
H5 H 0.0122(14) 0.5876(13) 0.600(2) 0.027(5) Uiso 1 1 d . . . . .
H9 H 0.2722(13) 0.7086(14) 0.083(2) 0.032(5) Uiso 1 1 d . . . . .
H14 H -0.0354(13) 0.6721(13) 0.393(2) 0.027(5) Uiso 1 1 d . . . . .
H12 H 0.1303(13) 0.7133(13) 0.097(2) 0.029(5) Uiso 1 1 d . . . . .
H2 H 0.4815(13) 0.4393(13) 0.370(2) 0.021(5) Uiso 1 1 d . . . . .
H7 H 0.4779(13) 0.5300(13) 0.164(2) 0.023(5) Uiso 1 1 d . . . . .
H8 H 0.4026(14) 0.6513(15) 0.018(2) 0.038(6) Uiso 1 1 d . . . . .
H18 H 0.1030(13) 0.4822(13) 1.064(2) 0.028(5) Uiso 1 1 d . . . . .
H4 H 0.5248(13) 0.3127(13) 0.505(2) 0.027(5) Uiso 1 1 d . . . . .
H20 H 0.2931(13) 0.4318(13) 0.824(2) 0.024(5) Uiso 1 1 d . . . . .
H1 H 0.2463(13) 0.3097(13) 0.623(2) 0.027(5) Uiso 1 1 d . . . . .
H19 H 0.2389(14) 0.4165(15) 1.053(2) 0.038(6) Uiso 1 1 d . . . . .
H3 H 0.4860(13) 0.1905(14) 0.656(2) 0.029(5) Uiso 1 1 d . . . . .
H2A H 0.3403(13) 0.1873(14) 0.706(2) 0.027(5) Uiso 1 1 d . . . . .
H13 H -0.0088(13) 0.7377(13) 0.169(2) 0.027(5) Uiso 1 1 d . . . . .
H17 H 0.0256(13) 0.5612(13) 0.848(2) 0.027(5) Uiso 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Co1 0.01231(9) 0.01578(9) 0.01503(9) 0.00244(7) 0.00418(7) 0.00214(7)
Cl1 0.01320(16) 0.01958(16) 0.02198(16) -0.00031(13) 0.00096(12) -0.00076(12)
Cl2 0.01497(17) 0.02944(19) 0.02290(17) -0.00876(14) 0.00481(13) -0.00383(14)
N6 0.0144(6) 0.0197(6) 0.0151(5) 0.0003(4) 0.0018(4) 0.0010(5)
N4 0.0154(6) 0.0128(5) 0.0170(5) 0.0003(4) 0.0036(4) 0.0000(4)
N2 0.0115(6) 0.0205(6) 0.0215(6) -0.0033(5) 0.0054(5) -0.0004(5)
N5 0.0113(6) 0.0217(6) 0.0187(6) 0.0014(5) 0.0035(4) 0.0030(5)
N1 0.0134(6) 0.0165(6) 0.0185(6) -0.0005(4) 0.0010(4) -0.0001(5)
N3 0.0155(6) 0.0145(6) 0.0157(5) -0.0011(4) 0.0037(4) -0.0015(4)
C16 0.0136(7) 0.0175(7) 0.0167(6) -0.0006(5) 0.0027(5) -0.0028(5)
C5 0.0149(7) 0.0178(7) 0.0153(6) -0.0048(5) -0.0001(5) -0.0002(5)
C15 0.0162(7) 0.0120(6) 0.0175(6) -0.0014(5) 0.0021(5) 0.0001(5)
C6 0.0161(7) 0.0164(7) 0.0174(6) -0.0041(5) 0.0045(5) -0.0040(5)
C17 0.0172(8) 0.0329(9) 0.0206(7) 0.0010(6) 0.0066(6) 0.0009(6)
C11 0.0222(7) 0.0144(7) 0.0195(7) 0.0021(5) 0.0058(5) 0.0005(5)
C4 0.0165(7) 0.0285(8) 0.0231(7) -0.0024(6) 0.0022(6) 0.0069(6)
C14 0.0177(7) 0.0178(7) 0.0236(7) -0.0008(5) 0.0008(6) 0.0042(6)
C1 0.0170(7) 0.0210(7) 0.0205(7) 0.0020(5) 0.0009(5) -0.0006(6)
C13 0.0268(8) 0.0206(8) 0.0266(8) 0.0065(6) 0.0004(6) 0.0093(6)
C2 0.0269(8) 0.0197(7) 0.0207(7) 0.0035(6) -0.0012(6) 0.0031(6)
C7 0.0218(8) 0.0274(8) 0.0254(8) -0.0023(6) 0.0121(6) -0.0046(6)
C10 0.0211(7) 0.0160(7) 0.0194(6) 0.0019(5) 0.0062(5) -0.0012(6)
C19 0.0276(9) 0.0314(9) 0.0171(7) 0.0033(6) 0.0010(6) -0.0001(7)
C20 0.0191(8) 0.0272(8) 0.0185(7) 0.0013(6) 0.0016(5) 0.0039(6)
C18 0.0254(8) 0.0358(9) 0.0173(7) 0.0018(6) 0.0067(6) -0.0041(7)
C3 0.0262(9) 0.0257(8) 0.0253(8) 0.0020(6) -0.0009(6) 0.0110(7)
C12 0.0321(9) 0.0226(8) 0.0236(8) 0.0091(6) 0.0073(6) 0.0070(7)
C9 0.0325(9) 0.0231(8) 0.0276(8) 0.0089(6) 0.0112(7) -0.0002(7)
C8 0.0317(9) 0.0298(9) 0.0291(8) 0.0055(7) 0.0152(7) -0.0067(7)
_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 N3 2.0684(12) . ?
Co1 N4 2.0691(12) . ?
Co1 N1 2.0747(12) . ?
Co1 N6 2.0828(12) . ?
Co1 Cl2 2.5499(4) . ?
Co1 Cl1 2.5701(4) . ?
N6 C16 1.3388(19) . ?
N6 C20 1.3597(19) . ?
N4 C15 1.3375(19) . ?
N4 C11 1.3606(18) . ?
N2 C5 1.3797(19) . ?
N2 C6 1.3827(19) . ?
N2 H2 0.807(19) . ?
N5 C15 1.3750(18) . ?
N5 C16 1.3861(18) . ?
N5 H5 0.85(2) . ?
N1 C5 1.3381(19) . ?
N1 C1 1.3548(19) . ?
N3 C6 1.3362(19) . ?
N3 C10 1.3592(18) . ?
C16 C17 1.406(2) . ?
C5 C4 1.409(2) . ?
C15 C14 1.409(2) . ?
C6 C7 1.409(2) . ?
C17 C18 1.370(2) . ?
C17 H17 0.95(2) . ?
C11 C12 1.381(2) . ?
C11 C10 1.480(2) . ?
C4 C3 1.367(2) . ?
C4 H4 0.94(2) . ?
C14 C13 1.371(2) . ?
C14 H14 0.92(2) . ?
C1 C2 1.368(2) . ?
C1 H1 0.97(2) . ?
C13 C12 1.393(2) . ?
C13 H13 0.943(19) . ?
C2 C3 1.394(2) . ?
C2 H2A 0.94(2) . ?
C7 C8 1.368(2) . ?
C7 H7 0.961(19) . ?
C10 C9 1.382(2) . ?
C19 C20 1.369(2) . ?
C19 C18 1.390(2) . ?
C19 H19 0.96(2) . ?
C20 H20 0.934(19) . ?
C18 H18 0.93(2) . ?
C3 H3 0.94(2) . ?
C12 H12 0.95(2) . ?
C9 C8 1.391(3) . ?
C9 H9 0.94(2) . ?
C8 H8 0.94(2) . ?
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
N3 Co1 N4 79.20(5) . . ?
N3 Co1 N1 88.33(5) . . ?
N4 Co1 N1 160.64(5) . . ?
N3 Co1 N6 162.60(5) . . ?
N4 Co1 N6 89.68(5) . . ?
N1 Co1 N6 105.60(5) . . ?
N3 Co1 Cl2 84.75(3) . . ?
N4 Co1 Cl2 102.64(3) . . ?
N1 Co1 Cl2 90.76(3) . . ?
N6 Co1 Cl2 84.69(4) . . ?
N3 Co1 Cl1 99.08(3) . . ?
N4 Co1 Cl1 83.41(3) . . ?
N1 Co1 Cl1 84.03(3) . . ?
N6 Co1 Cl1 92.81(4) . . ?
Cl2 Co1 Cl1 173.411(15) . . ?
C16 N6 C20 116.95(13) . . ?
C16 N6 Co1 124.29(10) . . ?
C20 N6 Co1 118.75(10) . . ?
C15 N4 C11 118.91(12) . . ?
C15 N4 Co1 124.06(9) . . ?
C11 N4 Co1 114.68(10) . . ?
C5 N2 C6 132.17(13) . . ?
C5 N2 H2 113.8(13) . . ?
C6 N2 H2 113.5(13) . . ?
C15 N5 C16 132.59(13) . . ?
C15 N5 H5 113.4(13) . . ?
C16 N5 H5 113.8(13) . . ?
C5 N1 C1 117.84(13) . . ?
C5 N1 Co1 123.64(10) . . ?
C1 N1 Co1 117.51(10) . . ?
C6 N3 C10 118.90(12) . . ?
C6 N3 Co1 125.51(10) . . ?
C10 N3 Co1 115.12(10) . . ?
N6 C16 N5 121.64(13) . . ?
N6 C16 C17 122.24(13) . . ?
N5 C16 C17 116.11(13) . . ?
N1 C5 N2 121.10(13) . . ?
N1 C5 C4 121.57(14) . . ?
N2 C5 C4 117.28(14) . . ?
N4 C15 N5 121.21(13) . . ?
N4 C15 C14 121.70(13) . . ?
N5 C15 C14 117.09(13) . . ?
N3 C6 N2 120.78(13) . . ?
N3 C6 C7 121.78(14) . . ?
N2 C6 C7 117.43(14) . . ?
C18 C17 C16 119.36(15) . . ?
C18 C17 H17 122.3(12) . . ?
C16 C17 H17 118.3(12) . . ?
N4 C11 C12 122.14(14) . . ?
N4 C11 C10 114.97(13) . . ?
C12 C11 C10 122.75(14) . . ?
C3 C4 C5 119.26(15) . . ?
C3 C4 H4 123.1(12) . . ?
C5 C4 H4 117.7(12) . . ?
C13 C14 C15 118.86(15) . . ?
C13 C14 H14 121.8(12) . . ?
C15 C14 H14 119.3(12) . . ?
N1 C1 C2 123.50(15) . . ?
N1 C1 H1 114.7(11) . . ?
C2 C1 H1 121.8(11) . . ?
C14 C13 C12 119.73(15) . . ?
C14 C13 H13 118.7(12) . . ?
C12 C13 H13 121.5(12) . . ?
C1 C2 C3 118.29(15) . . ?
C1 C2 H2A 118.6(12) . . ?
C3 C2 H2A 123.1(12) . . ?
C8 C7 C6 118.64(15) . . ?
C8 C7 H7 122.7(11) . . ?
C6 C7 H7 118.6(11) . . ?
N3 C10 C9 122.02(15) . . ?
N3 C10 C11 114.74(12) . . ?
C9 C10 C11 123.24(14) . . ?
C20 C19 C18 118.43(15) . . ?
C20 C19 H19 121.3(13) . . ?
C18 C19 H19 120.2(13) . . ?
N6 C20 C19 123.94(15) . . ?
N6 C20 H20 114.8(12) . . ?
C19 C20 H20 121.2(12) . . ?
C17 C18 C19 118.97(15) . . ?
C17 C18 H18 121.7(12) . . ?
C19 C18 H18 119.3(12) . . ?
C4 C3 C2 119.25(15) . . ?
C4 C3 H3 121.0(12) . . ?
C2 C3 H3 119.8(12) . . ?
C11 C12 C13 118.66(15) . . ?
C11 C12 H12 119.9(12) . . ?
C13 C12 H12 121.3(12) . . ?
C10 C9 C8 118.58(16) . . ?
C10 C9 H9 120.0(13) . . ?
C8 C9 H9 121.3(12) . . ?
C7 C8 C9 119.97(15) . . ?
C7 C8 H8 120.3(13) . . ?
C9 C8 H8 119.7(13) . . ?
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
N5 H5 Cl1 0.85(2) 2.34(2) 3.1903(13) 177.3(18) 3_566
N2 H2 Cl2 0.807(19) 2.39(2) 3.1997(13) 176.7(18) 3_666
_refine_diff_density_max 0.393
_refine_diff_density_min -0.333
_refine_diff_density_rms 0.061
_shelxl_version_number 2013-4
_shelx_res_file
;
TITL CF solution in P21/c
CELL 0.71073 15.476732 14.457408 8.895854 90 100.3316 90
ZERR 4 0.000272 0.000244 0.00014 0 0.0015 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Cl Co N
UNIT 80 64 8 4 24
EQIV $1 -X,1-Y,1-Z
EQIV $2 1-X,1-Y,1-Z
L.S. 4
PLAN 20
SIZE 0.129 0.138 0.243
TEMP -123
HTAB N5 Cl1_$1
HTAB N2 Cl2_$2
BOND $H
fmap 2
acta
SHEL 999 0.7
REM C:/Users/JP154903/structure/2015/dsv/queyriaux/nq373c/struct/tmp/nq37
REM 3c.hkl
WGHT 0.025400 1.122300
FVAR 4.15248
CO1 4 0.249868 0.497332 0.508446 11.00000 0.01231 0.01578 =
0.01503 0.00244 0.00418 0.00214
CL1 3 0.132022 0.389589 0.361573 11.00000 0.01320 0.01958 =
0.02198 -0.00031 0.00096 -0.00076
CL2 3 0.372613 0.588335 0.673846 11.00000 0.01497 0.02944 =
0.02290 -0.00876 0.00481 -0.00383
N6 5 0.193108 0.495441 0.703733 11.00000 0.01441 0.01974 =
0.01506 0.00031 0.00182 0.00098
N4 5 0.163098 0.600214 0.417464 11.00000 0.01539 0.01275 =
0.01702 0.00033 0.00357 0.00002
N2 5 0.432257 0.445531 0.386942 11.00000 0.01146 0.02054 =
0.02152 -0.00333 0.00539 -0.00044
N5 5 0.064669 0.577046 0.588700 11.00000 0.01134 0.02167 =
0.01869 0.00135 0.00352 0.00304
N1 5 0.328938 0.380618 0.523170 11.00000 0.01336 0.01652 =
0.01854 -0.00047 0.00104 -0.00010
N3 5 0.307206 0.541681 0.328261 11.00000 0.01551 0.01446 =
0.01567 -0.00108 0.00374 -0.00150
C16 1 0.115299 0.533380 0.712813 11.00000 0.01363 0.01752 =
0.01667 -0.00060 0.00266 -0.00281
C5 1 0.408275 0.379275 0.483265 11.00000 0.01486 0.01778 =
0.01530 -0.00478 -0.00006 -0.00018
C15 1 0.084449 0.613613 0.456260 11.00000 0.01624 0.01202 =
0.01749 -0.00141 0.00212 0.00014
C6 1 0.385046 0.513995 0.299761 11.00000 0.01614 0.01641 =
0.01740 -0.00408 0.00449 -0.00403
C17 1 0.079765 0.530624 0.847485 11.00000 0.01719 0.03291 =
0.02058 0.00095 0.00659 0.00087
C11 1 0.179300 0.637680 0.284987 11.00000 0.02215 0.01435 =
0.01952 0.00210 0.00583 0.00047
C4 1 0.469327 0.308516 0.532782 11.00000 0.01654 0.02846 =
0.02309 -0.00235 0.00223 0.00694
C14 1 0.018436 0.665718 0.363942 11.00000 0.01767 0.01781 =
0.02363 -0.00083 0.00083 0.00417
C1 1 0.305600 0.307104 0.601462 11.00000 0.01699 0.02105 =
0.02049 0.00196 0.00087 -0.00055
C13 1 0.035858 0.703947 0.231524 11.00000 0.02679 0.02065 =
0.02664 0.00645 0.00037 0.00934
C2 1 0.361036 0.235419 0.651435 11.00000 0.02694 0.01965 =
0.02068 0.00351 -0.00121 0.00310
C7 1 0.422659 0.553526 0.181807 11.00000 0.02178 0.02736 =
0.02543 -0.00235 0.01212 -0.00459
C10 1 0.265080 0.612512 0.245157 11.00000 0.02107 0.01600 =
0.01943 0.00185 0.00616 -0.00125
C19 1 0.205495 0.445931 0.965248 11.00000 0.02756 0.03142 =
0.01714 0.00327 0.00095 -0.00005
C20 1 0.237598 0.454455 0.832193 11.00000 0.01911 0.02725 =
0.01854 0.00133 0.00157 0.00388
C18 1 0.124589 0.485551 0.973067 11.00000 0.02544 0.03576 =
0.01732 0.00176 0.00669 -0.00415
C3 1 0.445774 0.237533 0.618556 11.00000 0.02622 0.02566 =
0.02529 0.00196 -0.00087 0.01100
C12 1 0.117648 0.690213 0.190431 11.00000 0.03209 0.02260 =
0.02357 0.00914 0.00727 0.00704
C9 1 0.300159 0.656480 0.131850 11.00000 0.03247 0.02308 =
0.02761 0.00891 0.01117 -0.00023
C8 1 0.379406 0.624536 0.098736 11.00000 0.03174 0.02975 =
0.02911 0.00546 0.01521 -0.00666
H5 2 0.012235 0.587556 0.599992 11.00000 0.02715
H9 2 0.272242 0.708559 0.082935 11.00000 0.03178
H14 2 -0.035410 0.672134 0.392871 11.00000 0.02699
H12 2 0.130332 0.713301 0.096528 11.00000 0.02869
H2 2 0.481528 0.439324 0.370475 11.00000 0.02107
H7 2 0.477941 0.529957 0.163844 11.00000 0.02282
H8 2 0.402590 0.651305 0.017954 11.00000 0.03785
H18 2 0.103038 0.482191 1.063965 11.00000 0.02843
H4 2 0.524807 0.312679 0.504637 11.00000 0.02740
H20 2 0.293051 0.431804 0.823823 11.00000 0.02400
H1 2 0.246298 0.309734 0.622625 11.00000 0.02710
H19 2 0.238914 0.416544 1.053039 11.00000 0.03813
H3 2 0.486009 0.190545 0.656174 11.00000 0.02945
H2A 2 0.340307 0.187267 0.705527 11.00000 0.02730
H13 2 -0.008799 0.737717 0.168890 11.00000 0.02717
H17 2 0.025639 0.561235 0.848228 11.00000 0.02664
HKLF 4
REM CF solution in P21/c
REM R1 = 0.0310 for 5015 Fo > 4sig(Fo) and 0.0418 for all 5983 data
REM 326 parameters refined using 0 restraints
END
WGHT 0.0254 1.1223
REM Highest difference peak 0.393, deepest hole -0.333, 1-sigma level 0.061
Q1 1 0.2883 0.6357 0.1982 11.00000 0.05 0.39
Q2 1 0.1127 0.5157 0.9075 11.00000 0.05 0.38
Q3 1 0.3407 0.2801 0.6511 11.00000 0.05 0.37
Q4 1 0.0484 0.6324 0.4011 11.00000 0.05 0.36
Q5 1 0.1736 0.6289 0.3532 11.00000 0.05 0.35
Q6 1 0.0738 0.5867 0.5143 11.00000 0.05 0.35
Q7 1 0.2226 0.6312 0.2545 11.00000 0.05 0.34
Q8 1 0.2220 0.4963 0.4171 11.00000 0.05 0.34
Q9 1 0.0993 0.5262 0.7828 11.00000 0.05 0.34
Q10 1 0.0970 0.5588 0.6497 11.00000 0.05 0.33
Q11 1 0.3529 0.6484 0.1368 11.00000 0.05 0.32
Q12 1 0.3216 0.3432 0.5573 11.00000 0.05 0.32
Q13 1 0.4097 0.2472 0.6594 11.00000 0.05 0.32
Q14 1 0.3725 0.3819 0.5146 11.00000 0.05 0.32
Q15 1 0.3462 0.5318 0.3204 11.00000 0.05 0.32
Q16 1 0.4513 0.3629 0.5380 11.00000 0.05 0.32
Q17 1 0.4329 0.3288 0.4859 11.00000 0.05 0.32
Q18 1 0.3927 0.5834 0.1373 11.00000 0.05 0.31
Q19 1 0.2175 0.4856 0.7734 11.00000 0.05 0.31
Q20 1 0.1674 0.4719 0.9593 11.00000 0.05 0.31
;
_shelx_res_checksum 77698
#######################################################################
#
# 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_nq373b
_database_code_depnum_ccdc_archive 'CCDC 1970565'
loop_
_audit_author_name
_audit_author_address
'Jacques Pecaut'
;Univ Grenoble Alpes, CEA, CNRS, IRIG, SYMMES
France
;
_audit_update_record
;
2019-12-06 deposited with the CCDC. 2020-05-11 downloaded from the CCDC.
;
_audit_creation_method SHELXL-2013
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C20 H16 Cl2 Co N6'
_chemical_formula_weight 470.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system monoclinic
_space_group_IT_number 15
_space_group_name_H-M_alt 'I 2/a'
_space_group_name_Hall '-I 2ya'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
_cell_length_a 13.3526(14)
_cell_length_b 18.7885(15)
_cell_length_c 16.0864(17)
_cell_angle_alpha 90
_cell_angle_beta 110.170(12)
_cell_angle_gamma 90
_cell_volume 3788.2(7)
_cell_formula_units_Z 8
_cell_measurement_temperature 150(2)
_cell_measurement_reflns_used 2896
_cell_measurement_theta_min 2.7110
_cell_measurement_theta_max 31.0420
_exptl_crystal_description 'triangular prism'
_exptl_crystal_colour 'translucent dark brown'
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_density_diffrn 1.649
_exptl_crystal_F_000 1912
_exptl_transmission_factor_min ?
_exptl_transmission_factor_max ?
_exptl_crystal_size_max 0.426
_exptl_crystal_size_mid 0.235
_exptl_crystal_size_min 0.079
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1 0 1 0.0393 -0.9943 0.0001 1.0003 -0.0017 -0.0010 0.0596
0 2 -1 0.2021 -0.0058 1.9998 -0.9960 0.0178 -0.0842 -0.0225
0 -1 0 0.1523 0.0009 -0.9995 -0.0012 0.0113 0.0360 0.0009
1 2 2 0.0605 1.0045 1.9962 1.9971 -0.1421 -0.0344 0.0005
-1 0 0 0.0552 -0.9983 0.0009 0.0020 0.0387 -0.0132 0.0389
1 0 -1 0.0393 0.9943 -0.0001 -1.0003 0.0017 0.0010 -0.0596
_exptl_absorpt_coefficient_mu 1.209
_shelx_estimated_absorpt_T_min 0.627
_shelx_estimated_absorpt_T_max 0.911
_exptl_absorpt_correction_type analytical
_exptl_absorpt_correction_T_min 0.924
_exptl_absorpt_correction_T_max 0.978
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 150(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_source 'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type 'Xcalibur, Sapphire3'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean 15.9653
_diffrn_reflns_number 11661
_diffrn_reflns_av_unetI/netI 0.0853
_diffrn_reflns_av_R_equivalents 0.0469
_diffrn_reflns_limit_h_min -19
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_k_max 26
_diffrn_reflns_limit_l_min -21
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_theta_min 1.953
_diffrn_reflns_theta_max 30.505
_diffrn_reflns_theta_full 25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total 5742
_reflns_number_gt 4160
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_max .
_reflns_Friedel_fraction_full .
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_computing_data_collection
;
Agilent Technologies, (2014), CrysAlisPro Software system,
version 1.171.37.35, Agilent Technologies UK Ltd, Oxford, UK
;
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
1 omega 32.00 102.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 25.5614 -178.0000 -60.0000 70
#__ type_ start__ end____ width___ exp.time_
2 omega -21.00 68.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 25.5614 -99.0000 -60.0000 89
#__ type_ start__ end____ width___ exp.time_
3 omega -61.00 35.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -26.9676 19.0000 0.0000 96
;
_computing_cell_refinement
;
Agilent Technologies, (2014), CrysAlisPro Software system,
version 1.171. 37.35, Agilent Technologies UK Ltd, Oxford, UK
;
_computing_data_reduction
;
Agilent Technologies, (2014), CrysAlisPro Software system,
version 1.171. 37.35, Agilent Technologies UK Ltd, Oxford, UK
;
_computing_structure_solution
;
SUPERFLIP program (Palatinus, L. & Chapuis, G. J. Appl. Cryst., 2007,
40, 786-790)
;
_computing_structure_refinement
;
OLEX2: a complete structure solution, refinement and analysis program
(O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and
H. Puschmann. J. Appl. Cryst. 2009, 42, 339-34).
;
_computing_molecular_graphics
;
Mercury 3.1 New software for searching the Cambridge Structural Database
and visualizing crystal structures (I.J. Bruno, J.C. Cole, P.R. Edgington,
M. Kessler, C.F. Macrae, P. McCabe, J. Pearson, R. Taylor,
Acta Cryst., 2002, B58, 389-397)
;
_computing_publication_material
;
SHELXL-2013
(Sheldrick, Acta Cryst. A64, 112-122)
;
_refine_special_details
;
?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0442P)^2^+3.4193P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_number_reflns 5742
_refine_ls_number_parameters 262
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0919
_refine_ls_R_factor_gt 0.0635
_refine_ls_wR_factor_ref 0.1418
_refine_ls_wR_factor_gt 0.1278
_refine_ls_goodness_of_fit_ref 1.126
_refine_ls_restrained_S_all 1.126
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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 0.51323(4) 0.30951(2) 0.12392(3) 0.01571(12) Uani 1 1 d . . . . .
Cl1 Cl 0.67879(6) 0.33010(5) 0.11319(5) 0.02235(19) Uani 1 1 d . . . . .
Cl2 Cl 0.23873(7) 0.07212(5) -0.15274(6) 0.0287(2) Uani 1 1 d . . . . .
N4 N 0.3868(2) 0.31065(14) 0.00559(17) 0.0137(5) Uani 1 1 d . . . . .
N3 N 0.4712(2) 0.41676(14) 0.11126(17) 0.0154(5) Uani 1 1 d . . . . .
N5 N 0.3683(2) 0.18531(14) -0.01074(17) 0.0176(6) Uani 1 1 d . . . . .
H5 H 0.3217 0.1530 -0.0401 0.021 Uiso 1 1 calc R U . . .
N1 N 0.5345(2) 0.32501(14) 0.25783(18) 0.0169(6) Uani 1 1 d . . . . .
C11 C 0.3558(2) 0.37695(16) -0.0295(2) 0.0144(6) Uani 1 1 d . . . . .
N2 N 0.5843(2) 0.44610(14) 0.25434(17) 0.0193(6) Uani 1 1 d . . . . .
H2 H 0.6368 0.4757 0.2806 0.023 Uiso 1 1 calc R U . . .
C10 C 0.4018(2) 0.43704(16) 0.0311(2) 0.0149(6) Uani 1 1 d . . . . .
C13 C 0.2401(3) 0.32634(19) -0.1642(2) 0.0197(7) Uani 1 1 d . . . . .
H13 H 0.1912 0.3316 -0.2229 0.024 Uiso 1 1 calc R U . . .
C17 C 0.4652(3) 0.08322(18) 0.0601(2) 0.0209(7) Uani 1 1 d . . . . .
H17 H 0.4142 0.0543 0.0179 0.025 Uiso 1 1 calc R U . . .
C7 C 0.4930(3) 0.53943(17) 0.1561(2) 0.0213(7) Uani 1 1 d . . . . .
H7 H 0.5262 0.5741 0.2000 0.026 Uiso 1 1 calc R U . . .
C9 C 0.3756(3) 0.50774(18) 0.0106(2) 0.0199(7) Uani 1 1 d . . . . .
H9 H 0.3273 0.5209 -0.0461 0.024 Uiso 1 1 calc R U . . .
C15 C 0.3425(2) 0.25306(17) -0.0426(2) 0.0154(6) Uani 1 1 d . . . . .
C3 C 0.6179(3) 0.3292(2) 0.4421(2) 0.0252(8) Uani 1 1 d . . . . .
H3 H 0.6484 0.3300 0.5049 0.030 Uiso 1 1 calc R U . . .
C14 C 0.2660(2) 0.25990(19) -0.1288(2) 0.0196(7) Uani 1 1 d . . . . .
H14 H 0.2332 0.2189 -0.1615 0.024 Uiso 1 1 calc R U . . .
C12 C 0.2851(3) 0.38653(19) -0.1146(2) 0.0190(7) Uani 1 1 d . . . . .
H12 H 0.2674 0.4329 -0.1386 0.023 Uiso 1 1 calc R U . . .
C5 C 0.5812(2) 0.38458(17) 0.3005(2) 0.0169(6) Uani 1 1 d . . . . .
N6 N 0.5213(2) 0.20004(14) 0.11886(17) 0.0178(6) Uani 1 1 d . . . . .
C4 C 0.6265(3) 0.38726(19) 0.3938(2) 0.0215(7) Uani 1 1 d . . . . .
H4 H 0.6625 0.4288 0.4226 0.026 Uiso 1 1 calc R U . . .
C16 C 0.4530(3) 0.15741(17) 0.0584(2) 0.0166(6) Uani 1 1 d . . . . .
C6 C 0.5154(3) 0.46707(17) 0.1722(2) 0.0176(6) Uani 1 1 d . . . . .
C1 C 0.5250(3) 0.26898(18) 0.3081(2) 0.0205(7) Uani 1 1 d . . . . .
H1 H 0.4892 0.2276 0.2787 0.025 Uiso 1 1 calc R U . . .
C19 C 0.6255(3) 0.09676(18) 0.1845(2) 0.0210(7) Uani 1 1 d . . . . .
H19 H 0.6870 0.0773 0.2281 0.025 Uiso 1 1 calc R U . . .
C20 C 0.6071(3) 0.16820(19) 0.1802(2) 0.0208(7) Uani 1 1 d . . . . .
H20 H 0.6571 0.1977 0.2225 0.025 Uiso 1 1 calc R U . . .
C18 C 0.5517(3) 0.05274(19) 0.1233(2) 0.0241(7) Uani 1 1 d . . . . .
H18 H 0.5613 0.0026 0.1255 0.029 Uiso 1 1 calc R U . . .
C8 C 0.4213(3) 0.55916(18) 0.0748(2) 0.0225(7) Uani 1 1 d . . . . .
H8 H 0.4031 0.6079 0.0626 0.027 Uiso 1 1 calc R U . . .
C2 C 0.5641(3) 0.2688(2) 0.3990(2) 0.0240(8) Uani 1 1 d . . . . .
H2A H 0.5548 0.2287 0.4315 0.029 Uiso 1 1 calc R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Co1 0.0191(2) 0.0122(2) 0.0120(2) -0.00158(16) 0.00050(17) -0.00153(17)
Cl1 0.0200(4) 0.0244(4) 0.0206(4) 0.0019(3) 0.0044(3) -0.0011(3)
Cl2 0.0307(5) 0.0217(4) 0.0276(5) -0.0093(4) 0.0025(4) -0.0085(4)
N4 0.0121(12) 0.0144(13) 0.0141(12) -0.0010(10) 0.0039(10) -0.0014(10)
N3 0.0176(13) 0.0132(13) 0.0128(12) -0.0014(10) 0.0021(10) -0.0031(10)
N5 0.0173(13) 0.0128(13) 0.0179(14) -0.0050(10) -0.0002(11) -0.0046(11)
N1 0.0177(13) 0.0163(14) 0.0165(13) -0.0005(11) 0.0055(11) 0.0000(11)
C11 0.0158(14) 0.0143(15) 0.0139(14) 0.0002(12) 0.0061(12) -0.0008(12)
N2 0.0228(14) 0.0146(14) 0.0159(13) -0.0022(11) 0.0008(11) -0.0069(11)
C10 0.0155(14) 0.0116(14) 0.0178(15) 0.0011(12) 0.0062(12) -0.0001(12)
C13 0.0150(15) 0.0304(19) 0.0104(14) -0.0038(13) 0.0001(12) 0.0008(13)
C17 0.0243(17) 0.0150(16) 0.0240(17) -0.0038(13) 0.0093(14) -0.0051(13)
C7 0.0295(18) 0.0127(16) 0.0220(17) -0.0029(13) 0.0093(14) -0.0028(14)
C9 0.0219(17) 0.0174(16) 0.0182(16) 0.0007(13) 0.0043(13) -0.0025(13)
C15 0.0132(14) 0.0163(15) 0.0166(15) -0.0031(12) 0.0052(12) -0.0007(12)
C3 0.0270(18) 0.034(2) 0.0131(16) 0.0022(14) 0.0046(14) 0.0066(16)
C14 0.0149(15) 0.0258(18) 0.0161(15) -0.0057(13) 0.0025(12) -0.0043(13)
C12 0.0204(16) 0.0208(17) 0.0149(15) 0.0017(13) 0.0048(13) -0.0002(14)
C5 0.0167(15) 0.0166(16) 0.0160(15) -0.0027(12) 0.0040(12) -0.0005(13)
N6 0.0177(13) 0.0168(14) 0.0159(13) -0.0026(11) 0.0017(11) -0.0023(11)
C4 0.0222(17) 0.0235(18) 0.0155(16) -0.0031(14) 0.0022(13) 0.0004(14)
C16 0.0177(15) 0.0159(16) 0.0154(15) -0.0017(12) 0.0045(13) -0.0029(13)
C6 0.0216(16) 0.0155(16) 0.0159(15) -0.0015(12) 0.0067(13) -0.0035(13)
C1 0.0227(17) 0.0153(16) 0.0235(17) 0.0000(13) 0.0079(14) 0.0020(13)
C19 0.0240(17) 0.0185(17) 0.0184(16) 0.0019(13) 0.0047(14) 0.0030(14)
C20 0.0188(16) 0.0207(17) 0.0183(16) -0.0008(13) 0.0006(13) 0.0002(14)
C18 0.0305(19) 0.0170(17) 0.0265(18) 0.0025(14) 0.0119(15) 0.0027(15)
C8 0.0295(18) 0.0113(15) 0.0261(18) 0.0038(13) 0.0090(15) 0.0007(14)
C2 0.0280(18) 0.0248(18) 0.0232(18) 0.0098(15) 0.0136(15) 0.0051(15)
_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 N6 2.063(3) . ?
Co1 N4 2.063(3) . ?
Co1 N3 2.083(3) . ?
Co1 N1 2.094(3) . ?
Co1 Cl1 2.3085(10) . ?
N4 C15 1.343(4) . ?
N4 C11 1.371(4) . ?
N3 C6 1.343(4) . ?
N3 C10 1.358(4) . ?
N5 C15 1.371(4) . ?
N5 C16 1.387(4) . ?
N5 H5 0.8800 . ?
N1 C5 1.349(4) . ?
N1 C1 1.360(4) . ?
C11 C12 1.380(4) . ?
C11 C10 1.479(4) . ?
N2 C6 1.382(4) . ?
N2 C5 1.382(4) . ?
N2 H2 0.8800 . ?
C10 C9 1.384(4) . ?
C13 C14 1.366(5) . ?
C13 C12 1.395(5) . ?
C13 H13 0.9500 . ?
C17 C18 1.373(5) . ?
C17 C16 1.403(4) . ?
C17 H17 0.9500 . ?
C7 C8 1.379(5) . ?
C7 C6 1.397(4) . ?
C7 H7 0.9500 . ?
C9 C8 1.392(5) . ?
C9 H9 0.9500 . ?
C15 C14 1.417(4) . ?
C3 C4 1.368(5) . ?
C3 C2 1.392(5) . ?
C3 H3 0.9500 . ?
C14 H14 0.9500 . ?
C12 H12 0.9500 . ?
C5 C4 1.411(4) . ?
N6 C16 1.345(4) . ?
N6 C20 1.365(4) . ?
C4 H4 0.9500 . ?
C1 C2 1.372(5) . ?
C1 H1 0.9500 . ?
C19 C20 1.362(5) . ?
C19 C18 1.398(5) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C18 H18 0.9500 . ?
C8 H8 0.9500 . ?
C2 H2A 0.9500 . ?
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
N6 Co1 N4 90.64(10) . . ?
N6 Co1 N3 167.64(10) . . ?
N4 Co1 N3 78.03(10) . . ?
N6 Co1 N1 100.89(10) . . ?
N4 Co1 N1 136.49(10) . . ?
N3 Co1 N1 84.40(10) . . ?
N6 Co1 Cl1 95.73(8) . . ?
N4 Co1 Cl1 115.42(7) . . ?
N3 Co1 Cl1 93.63(8) . . ?
N1 Co1 Cl1 105.07(8) . . ?
C15 N4 C11 118.9(3) . . ?
C15 N4 Co1 125.5(2) . . ?
C11 N4 Co1 115.1(2) . . ?
C6 N3 C10 118.7(3) . . ?
C6 N3 Co1 125.0(2) . . ?
C10 N3 Co1 115.9(2) . . ?
C15 N5 C16 132.9(3) . . ?
C15 N5 H5 113.6 . . ?
C16 N5 H5 113.6 . . ?
C5 N1 C1 117.4(3) . . ?
C5 N1 Co1 121.0(2) . . ?
C1 N1 Co1 119.8(2) . . ?
N4 C11 C12 122.2(3) . . ?
N4 C11 C10 115.1(3) . . ?
C12 C11 C10 122.7(3) . . ?
C6 N2 C5 128.3(3) . . ?
C6 N2 H2 115.9 . . ?
C5 N2 H2 115.9 . . ?
N3 C10 C9 121.9(3) . . ?
N3 C10 C11 113.8(3) . . ?
C9 C10 C11 124.2(3) . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C18 C17 C16 119.5(3) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C8 C7 C6 118.1(3) . . ?
C8 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
C10 C9 C8 118.7(3) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
N4 C15 N5 121.9(3) . . ?
N4 C15 C14 121.1(3) . . ?
N5 C15 C14 116.9(3) . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C13 C14 C15 119.0(3) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C11 C12 C13 118.3(3) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
N1 C5 N2 120.9(3) . . ?
N1 C5 C4 121.6(3) . . ?
N2 C5 C4 117.4(3) . . ?
C16 N6 C20 116.9(3) . . ?
C16 N6 Co1 126.2(2) . . ?
C20 N6 Co1 116.8(2) . . ?
C3 C4 C5 119.1(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N6 C16 N5 121.1(3) . . ?
N6 C16 C17 122.1(3) . . ?
N5 C16 C17 116.7(3) . . ?
N3 C6 N2 118.5(3) . . ?
N3 C6 C7 122.6(3) . . ?
N2 C6 C7 118.9(3) . . ?
N1 C1 C2 123.8(3) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C20 C19 C18 118.4(3) . . ?
C20 C19 H19 120.8 . . ?
C18 C19 H19 120.8 . . ?
C19 C20 N6 124.1(3) . . ?
C19 C20 H20 118.0 . . ?
N6 C20 H20 118.0 . . ?
C17 C18 C19 118.9(3) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C7 C8 C9 120.0(3) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C1 C2 C3 118.1(3) . . ?
C1 C2 H2A 121.0 . . ?
C3 C2 H2A 121.0 . . ?
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
C14 H14 Cl2 0.95 2.76 3.554(4) 141.5 .
N5 H5 Cl2 0.88 2.33 3.164(3) 157.5 .
N2 H2 Cl2 0.88 2.30 3.157(3) 165.4 3
_refine_diff_density_max 1.441
_refine_diff_density_min -0.579
_refine_diff_density_rms 0.134
_shelxl_version_number 2013-4
_shelx_res_file
;
TITL nq373b in I2/a #15
CELL 0.71073 13.352592 18.788495 16.086429 90 110.1703 90
ZERR 8 0.001402 0.001468 0.001658 0 0.0118 0
LATT 2
SYMM 0.5-X,+Y,-Z
SFAC C H Cl Co N
UNIT 160 128 16 8 48
EQIV $1 0.5+X,0.5+Y,0.5+Z
L.S. 4
PLAN 20
SIZE 0.079 0.235 0.426
TEMP -123
HTAB C14 Cl2
HTAB N5 Cl2
HTAB N2 Cl2_$1
REM reset to I2/a #15
BOND $H
ACTA
fmap 2
SHEL 999 0.7
REM C:/Users/JP154903/structure/2015/dsv/queyriaux/nq373b/struct/tmp/nq37
REM 3b.hkl
WGHT 0.044200 3.419300
FVAR 1.43688
CO1 4 0.513230 0.309514 0.123923 11.00000 0.01912 0.01221 =
0.01197 -0.00158 0.00050 -0.00153
CL1 3 0.678787 0.330098 0.113191 11.00000 0.02002 0.02441 =
0.02058 0.00192 0.00438 -0.00105
CL2 3 0.238730 0.072119 -0.152741 11.00000 0.03074 0.02173 =
0.02759 -0.00933 0.00245 -0.00854
N4 5 0.386794 0.310654 0.005588 11.00000 0.01209 0.01440 =
0.01406 -0.00099 0.00393 -0.00137
N3 5 0.471193 0.416762 0.111264 11.00000 0.01761 0.01316 =
0.01280 -0.00135 0.00206 -0.00314
N5 5 0.368255 0.185312 -0.010735 11.00000 0.01727 0.01282 =
0.01793 -0.00500 -0.00021 -0.00464
AFIX 43
H5 2 0.321681 0.153048 -0.040058 11.00000 -1.20000
AFIX 0
N1 5 0.534489 0.325013 0.257827 11.00000 0.01769 0.01634 =
0.01654 -0.00045 0.00553 -0.00005
C11 1 0.355812 0.376952 -0.029515 11.00000 0.01580 0.01430 =
0.01395 0.00017 0.00613 -0.00078
N2 5 0.584305 0.446103 0.254338 11.00000 0.02280 0.01463 =
0.01592 -0.00218 0.00081 -0.00686
AFIX 43
H2 2 0.636802 0.475680 0.280594 11.00000 -1.20000
AFIX 0
C10 1 0.401777 0.437037 0.031075 11.00000 0.01554 0.01162 =
0.01779 0.00110 0.00624 -0.00014
C13 1 0.240078 0.326341 -0.164237 11.00000 0.01499 0.03044 =
0.01037 -0.00379 0.00013 0.00080
AFIX 43
H13 2 0.191214 0.331593 -0.222949 11.00000 -1.20000
AFIX 0
C17 1 0.465248 0.083224 0.060106 11.00000 0.02433 0.01502 =
0.02400 -0.00376 0.00927 -0.00506
AFIX 43
H17 2 0.414163 0.054303 0.017875 11.00000 -1.20000
AFIX 0
C7 1 0.493024 0.539427 0.156133 11.00000 0.02949 0.01269 =
0.02199 -0.00294 0.00929 -0.00276
AFIX 43
H7 2 0.526233 0.574063 0.200013 11.00000 -1.20000
AFIX 0
C9 1 0.375570 0.507739 0.010615 11.00000 0.02186 0.01743 =
0.01823 0.00070 0.00430 -0.00252
AFIX 43
H9 2 0.327341 0.520900 -0.046075 11.00000 -1.20000
AFIX 0
C15 1 0.342515 0.253060 -0.042559 11.00000 0.01319 0.01633 =
0.01662 -0.00308 0.00516 -0.00074
C3 1 0.617882 0.329161 0.442109 11.00000 0.02696 0.03384 =
0.01309 0.00223 0.00461 0.00657
AFIX 43
H3 2 0.648443 0.329988 0.504891 11.00000 -1.20000
AFIX 0
C14 1 0.265987 0.259898 -0.128839 11.00000 0.01491 0.02578 =
0.01606 -0.00567 0.00252 -0.00429
AFIX 43
H14 2 0.233218 0.218913 -0.161548 11.00000 -1.20000
AFIX 0
C12 1 0.285057 0.386528 -0.114551 11.00000 0.02035 0.02085 =
0.01493 0.00169 0.00478 -0.00018
AFIX 43
H12 2 0.267424 0.432920 -0.138648 11.00000 -1.20000
AFIX 0
C5 1 0.581232 0.384582 0.300543 11.00000 0.01673 0.01658 =
0.01603 -0.00269 0.00405 -0.00047
N6 5 0.521287 0.200035 0.118859 11.00000 0.01768 0.01677 =
0.01588 -0.00257 0.00173 -0.00226
C4 1 0.626521 0.387259 0.393764 11.00000 0.02219 0.02349 =
0.01554 -0.00313 0.00219 0.00042
AFIX 43
H4 2 0.662521 0.428844 0.422555 11.00000 -1.20000
AFIX 0
C16 1 0.452962 0.157409 0.058396 11.00000 0.01771 0.01592 =
0.01536 -0.00166 0.00452 -0.00287
C6 1 0.515420 0.467068 0.172154 11.00000 0.02159 0.01545 =
0.01593 -0.00146 0.00666 -0.00351
C1 1 0.525005 0.268977 0.308141 11.00000 0.02274 0.01532 =
0.02346 0.00003 0.00787 0.00201
AFIX 43
H1 2 0.489209 0.227561 0.278666 11.00000 -1.20000
AFIX 0
C19 1 0.625508 0.096755 0.184505 11.00000 0.02400 0.01851 =
0.01841 0.00188 0.00474 0.00297
AFIX 43
H19 2 0.687032 0.077299 0.228062 11.00000 -1.20000
AFIX 0
C20 1 0.607102 0.168202 0.180189 11.00000 0.01878 0.02071 =
0.01832 -0.00080 0.00061 0.00024
AFIX 43
H20 2 0.657076 0.197717 0.222477 11.00000 -1.20000
AFIX 0
C18 1 0.551743 0.052738 0.123336 11.00000 0.03049 0.01698 =
0.02651 0.00254 0.01188 0.00266
AFIX 43
H18 2 0.561277 0.002579 0.125464 11.00000 -1.20000
AFIX 0
C8 1 0.421316 0.559162 0.074788 11.00000 0.02954 0.01134 =
0.02608 0.00384 0.00903 0.00066
AFIX 43
H8 2 0.403140 0.607879 0.062555 11.00000 -1.20000
AFIX 0
C2 1 0.564133 0.268809 0.398967 11.00000 0.02797 0.02475 =
0.02318 0.00979 0.01364 0.00511
AFIX 43
H2A 2 0.554834 0.228682 0.431499 11.00000 -1.20000
AFIX 0
HKLF 4
REM nq373b in I2/a #15
REM R1 = 0.0635 for 4160 Fo > 4sig(Fo) and 0.0919 for all 5742 data
REM 262 parameters refined using 0 restraints
END
WGHT 0.0442 3.4193
REM Highest difference peak 1.441, deepest hole -0.579, 1-sigma level 0.134
Q1 1 0.4563 0.3227 0.1290 11.00000 0.05 1.44
Q2 1 0.6142 0.3415 0.1073 11.00000 0.05 1.02
Q3 1 0.5800 0.3398 0.1425 11.00000 0.05 0.94
Q4 1 0.5829 0.2836 0.1395 11.00000 0.05 0.88
Q5 1 0.4591 0.2787 0.1090 11.00000 0.05 0.85
Q6 1 0.3031 0.1011 -0.1334 11.00000 0.05 0.75
Q7 1 0.5165 0.2495 0.1282 11.00000 0.05 0.74
Q8 1 0.3232 0.0500 -0.1369 11.00000 0.05 0.65
Q9 1 0.2305 0.0528 -0.1070 11.00000 0.05 0.59
Q10 1 0.5415 0.3513 0.0825 11.00000 0.05 0.56
Q11 1 0.3882 0.3079 0.0838 11.00000 0.05 0.55
Q12 1 0.1966 0.2971 -0.1541 11.00000 0.05 0.54
Q13 1 0.1815 0.0422 -0.1635 11.00000 0.05 0.54
Q14 1 0.4883 0.1776 0.0916 11.00000 0.05 0.54
Q15 1 0.5053 0.3700 0.1234 11.00000 0.05 0.54
Q16 1 0.6354 0.3148 0.1602 11.00000 0.05 0.52
Q17 1 0.4864 0.5387 0.0932 11.00000 0.05 0.51
Q18 1 0.2477 0.3492 -0.1341 11.00000 0.05 0.48
Q19 1 0.1884 0.0937 -0.1668 11.00000 0.05 0.48
Q20 1 0.5372 0.4940 0.1528 11.00000 0.05 0.48
;
_shelx_res_checksum 6758