#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:43:38 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223590 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/18/7231840.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_7231840
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         '0.5(C52 H32 Cl4 N8 O8 Zn2), C2 H3 N'
_chemical_formula_sum            'C28 H19 Cl2 N5 O4 Zn'
_chemical_formula_weight         625.75
_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_Hall           '-P 2a 2bc'
_space_group_name_H-M_alt        'P n n a'
_symmetry_space_group_name_Hall  '-P 2a 2bc'
_symmetry_space_group_name_H-M   'P n n a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-06-04
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8226(4)
_cell_length_b                   23.0562(8)
_cell_length_c                   10.5332(3)
_cell_measurement_reflns_used    7375
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.883
_cell_measurement_theta_min      2.699
_cell_volume                     2628.33(15)
_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      100.01
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23530
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.096
_diffrn_reflns_theta_min         1.766
_exptl_absorpt_coefficient_mu    1.184
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0479 before and 0.0416 after correction. The Ratio of minimum to maximum transmission is 0.8758. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_description       block
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2901
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.198
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0351
_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)+(0.0122P)²+5.0542P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0794
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2542
_reflns_number_total             2901
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce01756e2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7231836--7231841.cif.'
_cod_database_code               7231840
_shelx_shelxl_version_number     2017/1
_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   0.911
_shelx_estimated_absorpt_t_min   0.764
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: N3(0.5) C14(0.5) C15(0.5) H15A(0.5) H15B(0.5) H15C(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C10(H10), C11(H11), C4(H4), C2(H2), C3(H3)
3.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'-x+1/2, y+1/2, -z+1/2'
'x, -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'
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 0.22314(4) 0.750000 0.250000 0.01694(10) Uani 1 2 d S T P . .
Cl1 Cl 0.11824(6) 0.68509(3) 0.13658(6) 0.02554(15) Uani 1 1 d . . . . .
O2 O 0.69061(17) 0.67931(7) 0.17677(17) 0.0235(4) Uani 1 1 d . . . . .
O1 O 0.37674(18) 0.54844(8) 0.1698(2) 0.0318(5) Uani 1 1 d . . . . .
N1 N 0.33877(19) 0.70648(8) 0.3729(2) 0.0169(4) Uani 1 1 d . . . . .
N2 N 0.53403(19) 0.61369(9) 0.16937(19) 0.0183(4) Uani 1 1 d . . . . .
C12 C 0.9210(2) 0.49033(10) 0.1499(2) 0.0187(5) Uani 1 1 d . . . . .
C13 C 0.7940(2) 0.47712(10) 0.1471(2) 0.0162(5) Uani 1 1 d . . . . .
C9 C 0.7490(2) 0.58092(10) 0.1489(2) 0.0176(5) Uani 1 1 d . . . . .
C1 C 0.3207(2) 0.71750(10) 0.4976(2) 0.0208(5) Uani 1 1 d . . . . .
H1 H 0.257396 0.743905 0.521197 0.025 Uiso 1 1 calc R . . . .
C8 C 0.6587(2) 0.62899(10) 0.1640(2) 0.0176(5) Uani 1 1 d . . . . .
C5 C 0.4280(2) 0.66932(10) 0.3380(2) 0.0190(5) Uani 1 1 d . . . . .
C10 C 0.8734(2) 0.59252(11) 0.1454(2) 0.0214(5) Uani 1 1 d . . . . .
H10 H 0.900943 0.631609 0.142206 0.026 Uiso 1 1 calc R . . . .
C6 C 0.4451(2) 0.66017(11) 0.1969(2) 0.0200(5) Uani 1 1 d . . . . .
H6A H 0.364410 0.650308 0.158228 0.024 Uiso 1 1 calc R . . . .
H6B H 0.474403 0.696726 0.157891 0.024 Uiso 1 1 calc R . . . .
C11 C 0.9602(2) 0.54741(11) 0.1464(3) 0.0228(5) Uani 1 1 d . . . . .
H11 H 1.045997 0.556040 0.144748 0.027 Uiso 1 1 calc R . . . .
C7 C 0.4867(2) 0.55701(11) 0.1622(2) 0.0208(5) Uani 1 1 d . . . . .
C4 C 0.5008(3) 0.64191(12) 0.4286(3) 0.0264(6) Uani 1 1 d . . . . .
H4 H 0.563233 0.615379 0.403092 0.032 Uiso 1 1 calc R . . . .
C2 C 0.3901(3) 0.69215(12) 0.5914(3) 0.0259(6) Uani 1 1 d . . . . .
H2 H 0.375290 0.700943 0.678239 0.031 Uiso 1 1 calc R . . . .
C3 C 0.4820(3) 0.65350(12) 0.5570(3) 0.0287(6) Uani 1 1 d . . . . .
H3 H 0.531387 0.635171 0.619800 0.034 Uiso 1 1 calc R . . . .
N3 N 0.6082(7) 0.5057(3) 0.4589(7) 0.065(2) Uani 0.5 1 d . . . A -1
C14 C 0.6905(7) 0.4914(3) 0.5174(7) 0.0443(16) Uani 0.5 1 d . . . A -1
C15 C 0.7949(6) 0.4707(4) 0.5917(7) 0.053(2) Uani 0.5 1 d . . . A -1
H15A H 0.872036 0.480790 0.548248 0.080 Uiso 0.5 1 calc GR . . A -1
H15B H 0.789502 0.428488 0.601026 0.080 Uiso 0.5 1 calc GR . . A -1
H15C H 0.793446 0.488904 0.675714 0.080 Uiso 0.5 1 calc GR . . A -1
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'
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'
Zn Zn 0.2839 1.4301 '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 Zn1 Cl1 118.68(4) . 4_565
N1 Zn1 Cl1 108.62(6) . .
N1 Zn1 Cl1 108.62(6) 4_565 4_565
N1 Zn1 Cl1 107.46(6) . 4_565
N1 Zn1 Cl1 107.46(6) 4_565 .
N1 Zn1 N1 105.22(11) 4_565 .
C1 N1 Zn1 115.52(16) . .
C5 N1 Zn1 125.16(17) . .
C5 N1 C1 119.3(2) . .
C8 N2 C6 117.2(2) . .
C8 N2 C7 125.8(2) . .
C7 N2 C6 116.7(2) . .
C13 C12 C7 120.0(2) . 2_665
C11 C12 C13 120.3(2) . .
C11 C12 C7 119.7(2) . 2_665
C12 C13 C13 119.5(3) . 2_665
C12 C13 C9 121.6(2) . 2_665
C9 C13 C13 118.8(3) 2_665 2_665
C13 C9 C8 119.3(2) 2_665 .
C10 C9 C13 120.4(2) . 2_665
C10 C9 C8 120.2(2) . .
N1 C1 H1 118.6 . .
N1 C1 C2 122.8(2) . .
C2 C1 H1 118.6 . .
O2 C8 N2 120.7(2) . .
O2 C8 C9 122.4(2) . .
N2 C8 C9 116.9(2) . .
N1 C5 C6 116.5(2) . .
N1 C5 C4 120.7(2) . .
C4 C5 C6 122.8(2) . .
C9 C10 H10 119.6 . .
C9 C10 C11 120.8(2) . .
C11 C10 H10 119.6 . .
N2 C6 C5 112.1(2) . .
N2 C6 H6A 109.2 . .
N2 C6 H6B 109.2 . .
C5 C6 H6A 109.2 . .
C5 C6 H6B 109.2 . .
H6A C6 H6B 107.9 . .
C12 C11 C10 120.0(2) . .
C12 C11 H11 120.0 . .
C10 C11 H11 120.0 . .
O1 C7 N2 120.5(2) . .
O1 C7 C12 123.2(2) . 2_665
N2 C7 C12 116.3(2) . 2_665
C5 C4 H4 120.1 . .
C5 C4 C3 119.7(2) . .
C3 C4 H4 120.1 . .
C1 C2 H2 120.7 . .
C1 C2 C3 118.6(2) . .
C3 C2 H2 120.7 . .
C4 C3 H3 120.6 . .
C2 C3 C4 118.9(3) . .
C2 C3 H3 120.6 . .
N3 C14 C15 177.9(8) . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 Cl1 2.2261(6) .
Zn1 Cl1 2.2261(6) 4_565
Zn1 N1 2.061(2) 4_565
Zn1 N1 2.061(2) .
O2 C8 1.218(3) .
O1 C7 1.209(3) .
N1 C1 1.352(3) .
N1 C5 1.342(3) .
N2 C8 1.395(3) .
N2 C6 1.470(3) .
N2 C7 1.405(3) .
C12 C13 1.408(3) .
C12 C11 1.383(3) .
C12 C7 1.485(3) 2_665
C13 C13 1.421(5) 2_665
C13 C9 1.417(3) 2_665
C9 C8 1.487(3) .
C9 C10 1.373(4) .
C1 H1 0.9500 .
C1 C2 1.372(4) .
C5 C6 1.512(3) .
C5 C4 1.390(4) .
C10 H10 0.9500 .
C10 C11 1.402(4) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C11 H11 0.9500 .
C4 H4 0.9500 .
C4 C3 1.393(4) .
C2 H2 0.9500 .
C2 C3 1.384(4) .
C3 H3 0.9500 .
N3 C14 1.132(9) .
C14 C15 1.455(10) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
