#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:43:38 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223590 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/18/7231837.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_7231837
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), 3(C3 H6 O)'
_chemical_formula_sum            'C35 H34 Cl2 N4 O7 Zn'
_chemical_formula_weight         758.93
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-12-20
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2018-10-12 deposited with the CCDC.
2018-11-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.587(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.1935(6)
_cell_length_b                   9.2331(5)
_cell_length_c                   16.7061(8)
_cell_measurement_reflns_used    9133
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.34
_cell_measurement_theta_min      2.205
_cell_volume                     1721.06(15)
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.99
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            69088
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         36.422
_diffrn_reflns_theta_min         1.825
_diffrn_source                   'sealed tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.923
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.6933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0395 before and 0.0358 after correction.
The Ratio of minimum to maximum transmission is 0.9280.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.644
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         8423
_refine_ls_number_restraints     29
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0270
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0420P)²+0.4340P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0785
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7226
_reflns_number_total             8423
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce01756e2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7231836--7231841.cif.'
_cod_database_code               7231837
_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   0.922
_shelx_estimated_absorpt_t_min   0.802
_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. Restrained distances
 O3-C17
 2.35 with sigma of 0.01
 O3-C19
 2.35 with sigma of 0.01
 C18-C19 = C18-C17
 1.49 with sigma of 0.01
 O3-C18
 1.2 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C19) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C18)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.005
4. Others
 Fixed Sof: C19(0.5) H19A(0.5) H19B(0.5) H19C(0.5) O3(0.5) C17(0.5) H17A(0.5)
 H17B(0.5) H17C(0.5) C18(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
5.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C4(H4), C12(H12), C2(H2), C1(H1), C3(H3)
5.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C14(H14A,H14B,H14C), C19(H19A,H19B,H19C), C17(H17A,H17B,
 H17C)
;
_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+1/2'
'-x, -y, -z'
'x, -y, 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 1.0000 1.01671(2) 0.7500 0.01317(3) Uani 1 2 d S T P . .
Cl1 Cl 1.16875(2) 1.14251(2) 0.77683(2) 0.02239(5) Uani 1 1 d . . . . .
O2 O 0.83586(6) 0.49014(7) 0.63127(4) 0.01829(11) Uani 1 1 d . . . . .
O1 O 0.64961(6) 0.90905(7) 0.55475(4) 0.02088(12) Uani 1 1 d . . . . .
N2 N 0.73561(6) 0.69892(7) 0.60063(4) 0.01282(10) Uani 1 1 d . . . . .
N1 N 1.02114(6) 0.90053(7) 0.64565(4) 0.01363(11) Uani 1 1 d . . . . .
O4 O 0.25612(8) 0.35130(14) 0.58764(5) 0.0443(3) Uani 1 1 d . . . . .
C5 C 0.93880(6) 0.81462(8) 0.60553(4) 0.01228(11) Uani 1 1 d . . . . .
C8 C 0.74642(7) 0.54792(8) 0.59958(5) 0.01315(12) Uani 1 1 d . . . . .
C10 C 0.54759(6) 0.53996(8) 0.51964(4) 0.01159(11) Uani 1 1 d . . . . .
C13 C 0.45545(6) 0.30723(8) 0.48256(5) 0.01275(12) Uani 1 1 d . . . . .
C7 C 0.64492(7) 0.77710(8) 0.55752(5) 0.01392(12) Uani 1 1 d . . . . .
C6 C 0.82816(7) 0.78070(9) 0.64836(5) 0.01390(12) Uani 1 1 d . . . . .
H6A H 0.8526 0.7247 0.6975 0.017 Uiso 1 1 calc R . . . .
H6B H 0.7929 0.8729 0.6654 0.017 Uiso 1 1 calc R . . . .
C9 C 0.64503(6) 0.46536(8) 0.55953(5) 0.01220(11) Uani 1 1 d . . . . .
C11 C 0.64622(7) 0.31571(8) 0.56152(5) 0.01454(12) Uani 1 1 d . . . . .
H11 H 0.7115 0.2662 0.5892 0.017 Uiso 1 1 calc R . . . .
C4 C 0.95581(7) 0.76149(9) 0.52956(5) 0.01613(13) Uani 1 1 d . . . . .
H4 H 0.8973 0.7003 0.5027 0.019 Uiso 1 1 calc R . . . .
C12 C 0.55088(7) 0.23621(8) 0.52263(5) 0.01518(13) Uani 1 1 d . . . . .
H12 H 0.5524 0.1334 0.5240 0.018 Uiso 1 1 calc R . . . .
C2 C 1.14276(8) 0.88790(11) 0.53353(6) 0.02137(16) Uani 1 1 d . . . . .
H2 H 1.2137 0.9155 0.5098 0.026 Uiso 1 1 calc R . . . .
C1 C 1.12075(8) 0.93611(10) 0.60939(6) 0.01947(15) Uani 1 1 d . . . . .
H1 H 1.1784 0.9971 0.6373 0.023 Uiso 1 1 calc R . . . .
C3 C 1.05897(8) 0.79833(10) 0.49292(5) 0.01942(15) Uani 1 1 d . . . . .
H3 H 1.0718 0.7627 0.4409 0.023 Uiso 1 1 calc R . . . .
C15 C 0.24888(8) 0.42656(13) 0.64633(5) 0.02392(17) Uani 1 1 d . . . . .
C16 C 0.13441(12) 0.49744(15) 0.66407(8) 0.0348(2) Uani 1 1 d . . . . .
H16A H 0.0709 0.4694 0.6233 0.052 Uiso 1 1 calc GR . . . .
H16B H 0.1444 0.6029 0.6635 0.052 Uiso 1 1 calc GR . . . .
H16C H 0.1126 0.4667 0.7171 0.052 Uiso 1 1 calc GR . . . .
C14 C 0.35574(10) 0.44754(17) 0.70486(7) 0.0347(2) Uani 1 1 d . . . . .
H14A H 0.3427 0.3976 0.7552 0.052 Uiso 1 1 calc GR . . . .
H14B H 0.3676 0.5512 0.7154 0.052 Uiso 1 1 calc GR . . . .
H14C H 0.4270 0.4076 0.6824 0.052 Uiso 1 1 calc GR . . . .
C19 C 0.5615(6) 0.9727(6) 0.8196(3) 0.0659(17) Uani 0.5 1 d D U . A -1
H19A H 0.4938 1.0057 0.8486 0.099 Uiso 0.5 1 calc GR . . A -1
H19B H 0.6152 1.0545 0.8118 0.099 Uiso 0.5 1 calc GR . . A -1
H19C H 0.6055 0.8971 0.8508 0.099 Uiso 0.5 1 calc GR . . A -1
O3 O 0.5366(4) 0.7902(3) 0.7271(2) 0.0969(12) Uani 0.5 1 d D U . A -1
C17 C 0.4575(5) 1.0210(5) 0.6830(3) 0.0455(10) Uani 0.5 1 d D U . A -1
H17A H 0.3920 1.0702 0.7076 0.068 Uiso 0.5 1 calc GR . . A -1
H17B H 0.4253 0.9688 0.6349 0.068 Uiso 0.5 1 calc GR . . A -1
H17C H 0.5162 1.0927 0.6680 0.068 Uiso 0.5 1 calc GR . . A -1
C18 C 0.5174(3) 0.9149(3) 0.7423(2) 0.0406(6) Uani 0.5 1 d D U . 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 117.284(14) 2_756 .
N1 Zn1 Cl1 106.614(19) 2_756 2_756
N1 Zn1 Cl1 104.58(2) 2_756 .
N1 Zn1 Cl1 106.615(19) . .
N1 Zn1 Cl1 104.58(2) . 2_756
N1 Zn1 N1 117.79(4) 2_756 .
C8 N2 C6 117.52(6) . .
C7 N2 C8 124.60(6) . .
C7 N2 C6 117.85(6) . .
C5 N1 Zn1 126.87(5) . .
C1 N1 Zn1 113.84(5) . .
C1 N1 C5 118.33(7) . .
N1 C5 C6 116.01(6) . .
N1 C5 C4 121.50(7) . .
C4 C5 C6 122.49(7) . .
O2 C8 N2 119.99(7) . .
O2 C8 C9 122.98(7) . .
N2 C8 C9 117.02(6) . .
C13 C10 C10 119.60(8) 3_666 3_666
C9 C10 C10 119.32(8) . 3_666
C9 C10 C13 121.07(7) . 3_666
C10 C13 C7 119.83(6) 3_666 3_666
C12 C13 C10 120.24(7) . 3_666
C12 C13 C7 119.92(7) . 3_666
O1 C7 N2 120.22(7) . .
O1 C7 C13 122.73(7) . 3_666
N2 C7 C13 117.04(7) . 3_666
N2 C6 C5 114.80(6) . .
N2 C6 H6A 108.6 . .
N2 C6 H6B 108.6 . .
C5 C6 H6A 108.6 . .
C5 C6 H6B 108.6 . .
H6A C6 H6B 107.5 . .
C10 C9 C8 119.82(7) . .
C11 C9 C8 119.86(7) . .
C11 C9 C10 120.32(7) . .
C9 C11 H11 119.9 . .
C9 C11 C12 120.25(7) . .
C12 C11 H11 119.9 . .
C5 C4 H4 120.2 . .
C5 C4 C3 119.68(7) . .
C3 C4 H4 120.2 . .
C13 C12 C11 120.26(7) . .
C13 C12 H12 119.9 . .
C11 C12 H12 119.9 . .
C1 C2 H2 120.8 . .
C1 C2 C3 118.49(8) . .
C3 C2 H2 120.8 . .
N1 C1 C2 123.09(8) . .
N1 C1 H1 118.5 . .
C2 C1 H1 118.5 . .
C4 C3 H3 120.6 . .
C2 C3 C4 118.90(8) . .
C2 C3 H3 120.6 . .
O4 C15 C16 121.88(9) . .
O4 C15 C14 120.15(10) . .
C16 C15 C14 117.95(10) . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16B 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C15 C14 H14A 109.5 . .
C15 C14 H14B 109.5 . .
C15 C14 H14C 109.5 . .
H14A C14 H14B 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
H19A C19 H19B 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H17A C17 H17B 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C18 C17 H17A 109.5 . .
C18 C17 H17B 109.5 . .
C18 C17 H17C 109.5 . .
C19 C18 C17 116.6(3) . .
O3 C18 C19 119.2(4) . .
O3 C18 C17 124.0(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 Cl1 2.2321(2) 2_756
Zn1 Cl1 2.2321(2) .
Zn1 N1 2.0765(7) 2_756
Zn1 N1 2.0765(7) .
O2 C8 1.2176(9) .
O1 C7 1.2205(10) .
N2 C8 1.3997(10) .
N2 C7 1.3977(10) .
N2 C6 1.4653(10) .
N1 C5 1.3525(10) .
N1 C1 1.3512(11) .
O4 C15 1.2096(13) .
C5 C6 1.5117(11) .
C5 C4 1.3879(11) .
C8 C9 1.4816(11) .
C10 C10 1.4137(14) 3_666
C10 C13 1.4117(10) 3_666
C10 C9 1.4114(10) .
C13 C10 1.4117(10) 3_666
C13 C7 1.4820(11) 3_666
C13 C12 1.3801(10) .
C7 C13 1.4820(11) 3_666
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C9 C11 1.3822(11) .
C11 H11 0.9500 .
C11 C12 1.4103(11) .
C4 H4 0.9500 .
C4 C3 1.3917(12) .
C12 H12 0.9500 .
C2 H2 0.9500 .
C2 C1 1.3839(12) .
C2 C3 1.3864(13) .
C1 H1 0.9500 .
C3 H3 0.9500 .
C15 C16 1.4895(16) .
C15 C14 1.4959(14) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C19 C18 1.448(6) .
O3 C18 1.202(3) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C17 C18 1.511(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_4
Zn1 N1 C5 C6 -10.77(10) . .
Zn1 N1 C5 C4 169.18(6) . .
Zn1 N1 C1 C2 -170.13(8) . .
O2 C8 C9 C10 -175.98(8) . .
O2 C8 C9 C11 4.13(12) . .
N2 C8 C9 C10 4.61(11) . .
N2 C8 C9 C11 -175.29(7) . .
N1 C5 C6 N2 174.52(7) . .
N1 C5 C4 C3 -0.82(12) . .
C5 N1 C1 C2 -0.51(14) . .
C5 C4 C3 C2 -0.02(14) . .
C8 N2 C7 O1 -171.82(8) . .
C8 N2 C7 C13 9.03(11) . 3_666
C8 N2 C6 C5 85.14(9) . .
C8 C9 C11 C12 -179.13(7) . .
C10 C10 C9 C8 178.84(8) 3_666 .
C10 C10 C9 C11 -1.27(13) 3_666 .
C10 C13 C12 C11 -0.15(12) 3_666 .
C10 C9 C11 C12 0.97(12) . .
C13 C10 C9 C8 -0.29(11) 3_666 .
C13 C10 C9 C11 179.60(8) 3_666 .
C7 N2 C8 O2 171.25(8) . .
C7 N2 C8 C9 -9.32(11) . .
C7 N2 C6 C5 -93.00(8) . .
C7 C13 C12 C11 -179.43(8) 3_666 .
C6 N2 C8 O2 -6.74(11) . .
C6 N2 C8 C9 172.69(6) . .
C6 N2 C7 O1 6.17(11) . .
C6 N2 C7 C13 -172.98(7) . 3_666
C6 C5 C4 C3 179.13(8) . .
C9 C11 C12 C13 -0.26(13) . .
C4 C5 C6 N2 -5.43(11) . .
C1 N1 C5 C6 -178.89(7) . .
C1 N1 C5 C4 1.07(12) . .
C1 C2 C3 C4 0.55(15) . .
C3 C2 C1 N1 -0.30(15) . .
