#------------------------------------------------------------------------------
#$Date: 2019-11-23 20:46:47 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234919 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/96/4349612.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4349612
loop_
_publ_author_name
'Lovitt, June I.'
'Hawes, Chris S.'
'Lynes, Amy D.'
'Haffner, Benjamin'
'Möbius, Matthias E.'
'Gunnlaugsson, Thorfinnur'
_publ_section_title
;
 Coordination chemistry of N-picolyl-1,8-naphthalimides: colourful low
 molecular weight metallo-gelators and unique chelation behaviours
;
_journal_issue                   2
_journal_name_full               'Inorganic Chemistry Frontiers'
_journal_page_first              296
_journal_paper_doi               10.1039/C6QI00498A
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C36 H24 Cl2 Co N4 O4'
_chemical_formula_sum            'C36 H24 Cl2 Co N4 O4'
_chemical_formula_weight         706.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-09-13
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2016-10-26 deposited with the CCDC.
2016-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.411(2)
_cell_angle_beta                 104.798(2)
_cell_angle_gamma                111.102(2)
_cell_formula_units_Z            1
_cell_length_a                   7.3935(4)
_cell_length_b                   9.1136(6)
_cell_length_c                   12.1362(7)
_cell_measurement_reflns_used    1486
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.93
_cell_measurement_theta_min      2.41
_cell_volume                     733.14(8)
_computing_cell_refinement       'SAINT V8.35A (2016)'
_computing_data_reduction        'SAINT V8.35A (2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0740
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5391
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         1.746
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.819
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0481 before and 0.0391 after correction.
The Ratio of minimum to maximum transmission is 0.8683.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            pink
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_description       block
_exptl_crystal_F_000             361
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.935
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3362
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0350P)²+0.5300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.1047
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2365
_reflns_number_total             3362
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6qi00498a2.cif
_cod_data_source_block           2
_cod_database_code               4349612
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.915
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Co1 Co 1.0000 0.5000 1.0000 0.01504(16) Uani 1 2 d S T P
Cl1 Cl 1.10806(11) 0.42595(9) 0.84578(6) 0.01987(19) Uani 1 1 d . . .
O1 O 0.6892(3) 0.3899(2) 0.88722(17) 0.0179(5) Uani 1 1 d . . .
O2 O 0.4652(3) 0.7528(3) 0.70762(18) 0.0219(5) Uani 1 1 d . . .
N1 N 1.0302(4) 0.7253(3) 0.9310(2) 0.0167(5) Uani 1 1 d . . .
N2 N 0.5736(4) 0.5691(3) 0.7971(2) 0.0150(5) Uani 1 1 d . . .
C1 C 1.2162(5) 0.8141(4) 0.9253(2) 0.0184(6) Uani 1 1 d . . .
H1 H 1.3187 0.7717 0.9466 0.022 Uiso 1 1 calc R . .
C2 C 1.2667(5) 0.9643(4) 0.8900(3) 0.0209(7) Uani 1 1 d . . .
H2 H 1.4009 1.0234 0.8880 0.025 Uiso 1 1 calc R . .
C3 C 1.1186(5) 1.0270(4) 0.8578(2) 0.0204(7) Uani 1 1 d . . .
H3 H 1.1486 1.1297 0.8334 0.025 Uiso 1 1 calc R . .
C4 C 0.9259(5) 0.9361(4) 0.8621(2) 0.0193(7) Uani 1 1 d . . .
H4 H 0.8209 0.9757 0.8398 0.023 Uiso 1 1 calc R . .
C5 C 0.8859(4) 0.7864(4) 0.8993(2) 0.0157(6) Uani 1 1 d . . .
C6 C 0.6756(4) 0.6833(4) 0.9010(2) 0.0170(6) Uani 1 1 d . . .
H6A H 0.6819 0.6255 0.9698 0.020 Uiso 1 1 calc R . .
H6B H 0.5974 0.7503 0.9055 0.020 Uiso 1 1 calc R . .
C7 C 0.5875(4) 0.4224(4) 0.7998(2) 0.0160(6) Uani 1 1 d . . .
C8 C 0.4771(4) 0.3084(4) 0.6977(2) 0.0158(6) Uani 1 1 d . . .
C9 C 0.4947(5) 0.1629(4) 0.6936(3) 0.0197(7) Uani 1 1 d . . .
H9 H 0.5816 0.1382 0.7565 0.024 Uiso 1 1 calc R . .
C10 C 0.3848(5) 0.0506(4) 0.5968(3) 0.0238(7) Uani 1 1 d . . .
H10 H 0.3961 -0.0499 0.5952 0.029 Uiso 1 1 calc R . .
C11 C 0.2615(5) 0.0861(4) 0.5048(3) 0.0227(7) Uani 1 1 d . . .
H11 H 0.1854 0.0087 0.4407 0.027 Uiso 1 1 calc R . .
C12 C 0.2459(5) 0.2364(4) 0.5040(3) 0.0186(7) Uani 1 1 d . . .
C13 C 0.1293(5) 0.2813(4) 0.4077(3) 0.0211(7) Uani 1 1 d . . .
H13 H 0.0508 0.2060 0.3426 0.025 Uiso 1 1 calc R . .
C14 C 0.1285(5) 0.4310(4) 0.4072(3) 0.0211(7) Uani 1 1 d . . .
H14 H 0.0523 0.4597 0.3414 0.025 Uiso 1 1 calc R . .
C15 C 0.2399(4) 0.5423(4) 0.5036(2) 0.0186(7) Uani 1 1 d . . .
H15 H 0.2405 0.6466 0.5025 0.022 Uiso 1 1 calc R . .
C16 C 0.3487(4) 0.5010(4) 0.6004(2) 0.0163(6) Uani 1 1 d . . .
C17 C 0.4622(4) 0.6187(4) 0.7018(2) 0.0172(6) Uani 1 1 d . . .
C18 C 0.3556(4) 0.3487(4) 0.6013(2) 0.0162(6) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
Cl1 Co1 Cl1 180.00(3) . 2_767
O1 Co1 Cl1 86.81(6) 2_767 2_767
O1 Co1 Cl1 93.19(6) . 2_767
O1 Co1 Cl1 93.19(6) 2_767 .
O1 Co1 Cl1 86.81(6) . .
O1 Co1 O1 180.00(11) 2_767 .
N1 Co1 Cl1 88.64(7) . .
N1 Co1 Cl1 91.36(7) 2_767 .
N1 Co1 Cl1 88.64(7) 2_767 2_767
N1 Co1 Cl1 91.36(7) . 2_767
N1 Co1 O1 89.42(8) 2_767 .
N1 Co1 O1 89.42(8) . 2_767
N1 Co1 O1 90.58(8) . .
N1 Co1 O1 90.58(8) 2_767 2_767
N1 Co1 N1 180.0 . 2_767
C7 O1 Co1 135.9(2) . .
C1 N1 Co1 115.27(19) . .
C1 N1 C5 117.6(3) . .
C5 N1 Co1 127.1(2) . .
C7 N2 C6 118.7(2) . .
C7 N2 C17 124.8(3) . .
C17 N2 C6 116.5(2) . .
N1 C1 H1 118.3 . .
N1 C1 C2 123.4(3) . .
C2 C1 H1 118.3 . .
C1 C2 H2 120.5 . .
C3 C2 C1 118.9(3) . .
C3 C2 H2 120.5 . .
C2 C3 H3 120.9 . .
C4 C3 C2 118.2(3) . .
C4 C3 H3 120.9 . .
C3 C4 H4 120.0 . .
C3 C4 C5 119.9(3) . .
C5 C4 H4 120.0 . .
N1 C5 C4 122.0(3) . .
N1 C5 C6 117.2(3) . .
C4 C5 C6 120.8(3) . .
N2 C6 C5 110.6(2) . .
N2 C6 H6A 109.5 . .
N2 C6 H6B 109.5 . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
H6A C6 H6B 108.1 . .
O1 C7 N2 120.2(3) . .
O1 C7 C8 122.1(3) . .
N2 C7 C8 117.7(2) . .
C9 C8 C7 120.1(3) . .
C9 C8 C18 119.8(3) . .
C18 C8 C7 120.1(3) . .
C8 C9 H9 119.7 . .
C8 C9 C10 120.5(3) . .
C10 C9 H9 119.7 . .
C9 C10 H10 119.9 . .
C11 C10 C9 120.1(3) . .
C11 C10 H10 119.9 . .
C10 C11 H11 119.5 . .
C10 C11 C12 121.0(3) . .
C12 C11 H11 119.5 . .
C11 C12 C13 122.7(3) . .
C18 C12 C11 118.8(3) . .
C18 C12 C13 118.4(3) . .
C12 C13 H13 119.5 . .
C14 C13 C12 121.1(3) . .
C14 C13 H13 119.5 . .
C13 C14 H14 120.0 . .
C13 C14 C15 120.1(3) . .
C15 C14 H14 120.0 . .
C14 C15 H15 119.8 . .
C16 C15 C14 120.4(3) . .
C16 C15 H15 119.8 . .
C15 C16 C17 119.7(3) . .
C15 C16 C18 120.2(3) . .
C18 C16 C17 120.1(3) . .
O2 C17 N2 119.3(3) . .
O2 C17 C16 124.1(3) . .
N2 C17 C16 116.6(3) . .
C12 C18 C8 119.6(3) . .
C16 C18 C8 120.6(3) . .
C16 C18 C12 119.8(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Co1 Cl1 2.3940(7) .
Co1 Cl1 2.3940(7) 2_767
Co1 O1 2.208(2) 2_767
Co1 O1 2.208(2) .
Co1 N1 2.181(2) .
Co1 N1 2.181(2) 2_767
O1 C7 1.239(3) .
O2 C17 1.215(4) .
N1 C1 1.341(4) .
N1 C5 1.348(4) .
N2 C6 1.474(4) .
N2 C7 1.378(4) .
N2 C17 1.418(3) .
C1 H1 0.9500 .
C1 C2 1.386(4) .
C2 H2 0.9500 .
C2 C3 1.383(4) .
C3 H3 0.9500 .
C3 C4 1.381(4) .
C4 H4 0.9500 .
C4 C5 1.393(4) .
C5 C6 1.505(4) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.462(4) .
C8 C9 1.380(4) .
C8 C18 1.421(4) .
C9 H9 0.9500 .
C9 C10 1.408(4) .
C10 H10 0.9500 .
C10 C11 1.371(4) .
C11 H11 0.9500 .
C11 C12 1.415(4) .
C12 C13 1.422(4) .
C12 C18 1.413(4) .
C13 H13 0.9500 .
C13 C14 1.367(4) .
C14 H14 0.9500 .
C14 C15 1.402(4) .
C15 H15 0.9500 .
C15 C16 1.381(4) .
C16 C17 1.475(4) .
C16 C18 1.407(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
Co1 O1 C7 N2 -51.8(4)
Co1 O1 C7 C8 129.0(3)
Co1 N1 C1 C2 -176.2(2)
Co1 N1 C5 C4 176.4(2)
Co1 N1 C5 C6 -6.0(4)
O1 C7 C8 C9 -4.4(5)
O1 C7 C8 C18 177.3(3)
N1 C1 C2 C3 -0.6(5)
N1 C5 C6 N2 -80.5(3)
N2 C7 C8 C9 176.5(3)
N2 C7 C8 C18 -1.9(4)
C1 N1 C5 C4 -0.2(4)
C1 N1 C5 C6 177.4(2)
C1 C2 C3 C4 -0.1(4)
C2 C3 C4 C5 0.6(4)
C3 C4 C5 N1 -0.5(4)
C3 C4 C5 C6 -178.0(3)
C4 C5 C6 N2 97.2(3)
C5 N1 C1 C2 0.8(4)
C6 N2 C7 O1 -2.1(4)
C6 N2 C7 C8 177.1(2)
C6 N2 C17 O2 4.1(4)
C6 N2 C17 C16 -176.0(2)
C7 N2 C6 C5 91.5(3)
C7 N2 C17 O2 -177.8(3)
C7 N2 C17 C16 2.1(4)
C7 C8 C9 C10 178.3(3)
C7 C8 C18 C12 -178.6(3)
C7 C8 C18 C16 3.5(4)
C8 C9 C10 C11 1.0(5)
C9 C8 C18 C12 3.1(4)
C9 C8 C18 C16 -174.9(3)
C9 C10 C11 C12 1.5(5)
C10 C11 C12 C13 176.1(3)
C10 C11 C12 C18 -1.8(5)
C11 C12 C13 C14 -175.6(3)
C11 C12 C18 C8 -0.6(4)
C11 C12 C18 C16 177.4(3)
C12 C13 C14 C15 -1.5(5)
C13 C12 C18 C8 -178.5(3)
C13 C12 C18 C16 -0.5(4)
C13 C14 C15 C16 -1.0(5)
C14 C15 C16 C17 -179.0(3)
C14 C15 C16 C18 2.7(4)
C15 C16 C17 O2 1.2(5)
C15 C16 C17 N2 -178.8(3)
C15 C16 C18 C8 176.1(3)
C15 C16 C18 C12 -1.9(4)
C17 N2 C6 C5 -90.3(3)
C17 N2 C7 O1 179.8(3)
C17 N2 C7 C8 -1.0(4)
C17 C16 C18 C8 -2.3(4)
C17 C16 C18 C12 179.8(3)
C18 C8 C9 C10 -3.3(5)
C18 C12 C13 C14 2.3(4)
C18 C16 C17 O2 179.5(3)
C18 C16 C17 N2 -0.4(4)
