#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:43:38 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223590 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/18/7231839.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_7231839
loop_
_publ_author_name
'Lovitt, June I.'
'Hawes, Chris S.'
'Gunnlaugsson, Thorfinnur'
_publ_section_title
;
 Crystallographic studies of 2-picolyl substituted naphthalene diimide and
 bis-phthalimide ligands and their supramolecular coordination chemistry
;
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              207
_journal_paper_doi               10.1039/C8CE01756E
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         '2(Cl), C26 H18 N4 O4'
_chemical_formula_sum            'C26 H18 Cl2 N4 O4'
_chemical_formula_weight         521.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-12 deposited with the CCDC.
2018-11-20 downloaded from the CCDC.
;
_cell_angle_alpha                109.588(15)
_cell_angle_beta                 98.253(15)
_cell_angle_gamma                91.039(16)
_cell_formula_units_Z            1
_cell_length_a                   4.9197(9)
_cell_length_b                   9.297(2)
_cell_length_c                   12.906(3)
_cell_measurement_reflns_used    277
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      53.88
_cell_measurement_theta_min      3.68
_cell_volume                     549.0(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.2359
_diffrn_reflns_av_unetI/netI     0.2619
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3697
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        54.366
_diffrn_reflns_theta_max         54.366
_diffrn_reflns_theta_min         3.682
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.049
_exptl_absorpt_correction_T_max  0.7507
_exptl_absorpt_correction_T_min  0.4232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1257 before and 0.0689 after correction. The Ratio of minimum to maximum transmission is 0.5637. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_description       needle
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         1337
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.963
_refine_ls_R_factor_all          0.1767
_refine_ls_R_factor_gt           0.0819
_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)+(0.0395P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1742
_refine_ls_wR_factor_ref         0.2223
_reflns_Friedel_coverage         0.000
_reflns_number_gt                660
_reflns_number_total             1337
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce01756e2.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 7231836--7231841.cif.'
_cod_database_code               7231839
_shelx_shelxl_version_number     2016/4
_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   0.942
_shelx_estimated_absorpt_t_min   0.815
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N4-H4
 0.9 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C1AA(H1AA), C12(H12), C13(H13), C4(H4A), C3(H3)
;
_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
Cl1 Cl 1.1764(5) 1.0981(3) 0.7137(2) 0.0325(8) Uani 1 1 d .
O4 O 0.2536(14) 0.8957(8) 0.9386(5) 0.0324(18) Uani 1 1 d .
O3 O 0.8866(14) 0.6012(8) 0.7595(6) 0.0319(19) Uani 1 1 d .
N3 N 0.5806(14) 0.7515(9) 0.8514(6) 0.024(2) Uani 1 1 d .
N4 N 0.6955(17) 0.8651(10) 0.6185(7) 0.030(2) Uani 1 1 d D
C0AA C 0.5543(19) 0.8045(12) 0.6771(8) 0.029(3) Uani 1 1 d .
C2 C 0.4908(18) 0.4489(11) 1.0306(8) 0.024(3) Uani 1 1 d .
C5 C 0.3397(19) 0.6954(11) 0.6178(8) 0.028(3) Uani 1 1 d .
H5 H 0.240401 0.645453 0.655449 0.034 Uiso 1 1 calc R
C11 C 0.6360(18) 0.3178(12) 1.0081(8) 0.026(3) Uani 1 1 d .
C6 C 0.632(2) 0.8639(12) 0.8012(7) 0.028(3) Uani 1 1 d .
H6A H 0.830578 0.898270 0.820539 0.034 Uiso 1 1 calc R
H6B H 0.527260 0.953946 0.832533 0.034 Uiso 1 1 calc R
C1AA C 0.6369(19) 0.8335(13) 0.5061(8) 0.030(3) Uani 1 1 d .
H1AA H 0.739790 0.884233 0.469938 0.035 Uiso 1 1 calc R
C8 C 0.730(2) 0.6208(12) 0.8270(9) 0.032(3) Uani 1 1 d .
C12 C 0.8027(19) 0.2851(13) 0.9276(8) 0.029(3) Uani 1 1 d .
H12 H 0.898991 0.194498 0.912220 0.035 Uiso 1 1 calc R
C7 C 0.387(2) 0.7855(14) 0.9268(8) 0.031(3) Uani 1 1 d .
C13 C 0.8324(18) 0.3856(12) 0.8673(7) 0.027(3) Uani 1 1 d .
H13 H 0.948642 0.362020 0.811902 0.032 Uiso 1 1 calc R
C14 C 0.6932(19) 0.5171(12) 0.8888(8) 0.028(3) Uani 1 1 d .
C4 C 0.269(2) 0.6590(12) 0.5006(8) 0.033(3) Uani 1 1 d .
H4A H 0.116721 0.588910 0.460115 0.040 Uiso 1 1 calc R
C3 C 0.425(2) 0.7265(14) 0.4467(9) 0.045(3) Uani 1 1 d .
H3 H 0.385615 0.698905 0.368018 0.054 Uiso 1 1 calc R
H4 H 0.824(16) 0.943(8) 0.657(7) 0.05(4) Uiso 1 1 d D
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C8 N3 C6 118.5(8) . .
C8 N3 C7 124.6(9) . .
C7 N3 C6 116.8(8) . .
C0AA N4 C1AA 125.1(9) . .
C0AA N4 H4 118(6) . .
C1AA N4 H4 117(6) . .
N4 C0AA C5 117.2(9) . .
N4 C0AA C6 117.5(9) . .
C5 C0AA C6 125.3(9) . .
C2 C2 C14 117.6(12) 2_667 2_667
C11 C2 C2 120.7(12) . 2_667
C11 C2 C14 121.6(9) . 2_667
C0AA C5 H5 120.1 . .
C0AA C5 C4 119.9(9) . .
C4 C5 H5 120.1 . .
C2 C11 C7 119.4(9) . 2_667
C12 C11 C2 120.4(10) . .
C12 C11 C7 120.2(10) . 2_667
N3 C6 C0AA 112.9(8) . .
N3 C6 H6A 109.0 . .
N3 C6 H6B 109.0 . .
C0AA C6 H6A 109.0 . .
C0AA C6 H6B 109.0 . .
H6A C6 H6B 107.8 . .
N4 C1AA H1AA 120.9 . .
N4 C1AA C3 118.1(9) . .
C3 C1AA H1AA 120.9 . .
O3 C8 N3 119.4(9) . .
O3 C8 C14 123.7(11) . .
N3 C8 C14 116.9(10) . .
C11 C12 H12 119.7 . .
C11 C12 C13 120.5(10) . .
C13 C12 H12 119.7 . .
O4 C7 N3 121.0(9) . .
O4 C7 C11 121.9(10) . 2_667
N3 C7 C11 117.1(10) . 2_667
C12 C13 H13 119.9 . .
C14 C13 C12 120.2(9) . .
C14 C13 H13 119.9 . .
C2 C14 C8 120.1(10) 2_667 .
C13 C14 C2 120.4(9) . 2_667
C13 C14 C8 119.5(10) . .
C5 C4 H4A 120.4 . .
C3 C4 C5 119.2(10) . .
C3 C4 H4A 120.4 . .
C1AA C3 C4 120.4(10) . .
C1AA C3 H3 119.8 . .
C4 C3 H3 119.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O4 C7 1.206(12) .
O3 C8 1.215(12) .
N3 C6 1.438(11) .
N3 C8 1.400(14) .
N3 C7 1.421(13) .
N4 C0AA 1.339(12) .
N4 C1AA 1.366(12) .
N4 H4 0.91(2) .
C0AA C5 1.392(14) .
C0AA C6 1.497(13) .
C2 C2 1.434(18) 2_667
C2 C11 1.391(14) .
C2 C14 1.436(14) 2_667
C5 H5 0.9500 .
C5 C4 1.422(13) .
C11 C12 1.373(13) .
C11 C7 1.486(13) 2_667
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C1AA H1AA 0.9500 .
C1AA C3 1.373(14) .
C8 C14 1.466(13) .
C12 H12 0.9500 .
C12 C13 1.420(13) .
C7 C11 1.486(13) 2_667
C13 H13 0.9500 .
C13 C14 1.378(14) .
C14 C2 1.436(14) 2_667
C4 H4A 0.9500 .
C4 C3 1.376(15) .
C3 H3 0.9500 .
