#------------------------------------------------------------------------------
#$Date: 2020-03-05 11:53:14 +0200 (Thu, 05 Mar 2020) $
#$Revision: 249078 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/73/1557389.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_1557389
loop_
_publ_author_name
'Park, In-Hyeok'
'Dey, Atanu'
'Sasaki, Kenta'
'Ohba, Masaaki'
'Lee, Shim Sung'
'Vittal, Jagadese J.'
_publ_section_title
;
 Disappeared supramolecular isomer reappears with perylene guest
;
_journal_issue                   2
_journal_name_full               IUCrJ
_journal_page_first              324
_journal_page_last               330
_journal_paper_doi               10.1107/S2052252520001451
_journal_volume                  7
_journal_year                    2020
_chemical_formula_sum            'C38 H26 N2 O6 Zn'
_chemical_formula_weight         671.98
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 124.421(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.180(4)
_cell_length_b                   14.880(2)
_cell_length_c                   18.158(3)
_cell_measurement_reflns_used    589
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.73
_cell_measurement_theta_min      3.53
_cell_volume                     6280.8(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.961
_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  0.0558
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            24805
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.008
_diffrn_reflns_theta_min         4.893
_exptl_absorpt_coefficient_mu    1.515
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_correction_T_min  0.794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2014)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2768
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.095
_refine_diff_density_max         0.661
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         6231
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0493P)²+23.1354P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1387
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4436
_reflns_number_total             6231
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lq5029.cif
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1557387--1557389.cif.
;
_cod_original_cell_volume        6280.7(17)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1557389
_shelx_shelxl_version_number     2014/7
_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_min   0.778
_shelx_estimated_absorpt_t_max   0.869
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.24734(2) 0.45792(3) 0.74726(3) 0.02143(13) Uani 1 1 d . . . . .
O1 O 0.26132(11) 0.39277(17) 0.84964(16) 0.0329(6) Uani 1 1 d . . . . .
O2 O 0.17040(12) 0.39789(17) 0.80473(16) 0.0358(6) Uani 1 1 d . . . . .
O3 O 0.13662(12) 0.3034(2) 0.88452(18) 0.0473(8) Uani 1 1 d . . . . .
H3 H 0.1334 0.3391 0.8461 0.071 Uiso 1 1 calc R U . . .
O4 O 0.24735(11) 0.36602(16) 0.67286(16) 0.0325(6) Uani 1 1 d . . . . .
O5 O 0.25546(11) 0.47145(16) 0.59406(16) 0.0307(6) Uani 1 1 d . . . . .
O6 O 0.25514(11) 0.42657(15) 0.45691(15) 0.0277(6) Uani 1 1 d . . . . .
H6 H 0.2553 0.4617 0.4933 0.042 Uiso 1 1 calc R U . . .
N1 N 0.18033(12) 0.54333(19) 0.67815(18) 0.0262(6) Uani 1 1 d . . . . .
C1 C 0.17031(16) 0.6009(2) 0.7244(2) 0.0297(8) Uani 1 1 d . . . . .
H1 H 0.1871 0.5895 0.7859 0.036 Uiso 1 1 calc R U . . .
C2 C 0.13640(17) 0.6763(2) 0.6858(2) 0.0338(9) Uani 1 1 d . . . . .
H2 H 0.1306 0.7163 0.7208 0.041 Uiso 1 1 calc R U . . .
C3 C 0.11062(16) 0.6937(3) 0.5948(2) 0.0319(9) Uani 1 1 d . . . . .
C4 C 0.11905(17) 0.6309(3) 0.5470(2) 0.0353(9) Uani 1 1 d . . . . .
H4 H 0.1008 0.6384 0.4846 0.042 Uiso 1 1 calc R U . . .
C5 C 0.15377(16) 0.5581(3) 0.5900(2) 0.0331(9) Uani 1 1 d . . . . .
H5 H 0.1594 0.5161 0.5562 0.040 Uiso 1 1 calc R U . . .
C6 C 0.07503(17) 0.7728(3) 0.5484(3) 0.0371(10) Uani 1 1 d . . . . .
H6A H 0.0543 0.7735 0.4851 0.045 Uiso 1 1 calc R U . . .
C7 C 0.06937(16) 0.8425(3) 0.5867(2) 0.0314(9) Uani 1 1 d . . . . .
H7 H 0.0900 0.8415 0.6499 0.038 Uiso 1 1 calc R U . . .
C8 C 0.03393(16) 0.9225(2) 0.5406(2) 0.0287(8) Uani 1 1 d . . . . .
C9 C 0.03088(16) 0.9890(3) 0.5912(2) 0.0311(9) Uani 1 1 d . . . . .
H9 H 0.0519 0.9819 0.6541 0.037 Uiso 1 1 calc R U . . .
C10 C -0.00215(16) 1.0656(3) 0.5522(2) 0.0310(8) Uani 1 1 d . . . . .
H10 H -0.0032 1.1103 0.5885 0.037 Uiso 1 1 calc R U . . .
N2 N 0.31249(12) 0.54923(18) 0.81065(17) 0.0226(6) Uani 1 1 d . . . . .
C11 C 0.34495(14) 0.5541(2) 0.9002(2) 0.0224(7) Uani 1 1 d . . . . .
H11 H 0.3429 0.5065 0.9332 0.027 Uiso 1 1 calc R U . . .
C12 C 0.38128(14) 0.6256(2) 0.9462(2) 0.0231(7) Uani 1 1 d . . . . .
H12 H 0.4036 0.6263 1.0096 0.028 Uiso 1 1 calc R U . . .
C13 C 0.38525(15) 0.6959(2) 0.9002(2) 0.0254(8) Uani 1 1 d . . . . .
C14 C 0.35230(16) 0.6896(2) 0.8068(2) 0.0306(9) Uani 1 1 d . . . . .
H14 H 0.3542 0.7356 0.7723 0.037 Uiso 1 1 calc R U . . .
C15 C 0.31742(16) 0.6165(2) 0.7660(2) 0.0284(8) Uani 1 1 d . . . . .
H15 H 0.2956 0.6132 0.7027 0.034 Uiso 1 1 calc R U . . .
C16 C 0.42278(15) 0.7726(2) 0.9491(2) 0.0254(8) Uani 1 1 d . . . . .
H16 H 0.4461 0.7691 1.0124 0.030 Uiso 1 1 calc R U . . .
C17 C 0.42693(15) 0.8471(2) 0.9120(2) 0.0246(8) Uani 1 1 d . . . . .
H17 H 0.4030 0.8502 0.8487 0.030 Uiso 1 1 calc R U . . .
C18 C 0.46427(14) 0.9241(2) 0.9583(2) 0.0231(7) Uani 1 1 d . . . . .
C19 C 0.46757(15) 0.9922(2) 0.9082(2) 0.0265(8) Uani 1 1 d . . . . .
H19 H 0.4453 0.9873 0.8450 0.032 Uiso 1 1 calc R U . . .
C20 C 0.50250(15) 1.0661(2) 0.9487(2) 0.0262(8) Uani 1 1 d . . . . .
H20 H 0.5040 1.1111 0.9130 0.031 Uiso 1 1 calc R U . . .
C21 C 0.22185(17) 0.3712(2) 0.8560(2) 0.0276(8) Uani 1 1 d . . . . .
C22 C 0.23594(16) 0.3094(2) 0.9312(2) 0.0273(8) Uani 1 1 d . . . . .
C23 C 0.19276(16) 0.2779(2) 0.9408(2) 0.0315(9) Uani 1 1 d . . . . .
C24 C 0.20759(17) 0.2184(2) 1.0098(2) 0.0317(9) Uani 1 1 d . . . . .
H24 H 0.1786 0.1965 1.0166 0.038 Uiso 1 1 calc R U . . .
C25 C 0.25164(14) 0.3894(2) 0.6132(2) 0.0220(7) Uani 1 1 d . . . . .
C26 C 0.24960(14) 0.3186(2) 0.5521(2) 0.0228(7) Uani 1 1 d . . . . .
C27 C 0.25281(14) 0.3398(2) 0.4793(2) 0.0220(7) Uani 1 1 d . . . . .
C28 C 0.25338(14) 0.2709(2) 0.4284(2) 0.0228(7) Uani 1 1 d . . . . .
H28 H 0.2558 0.2849 0.3796 0.027 Uiso 1 1 calc R U . . .
C29 C 0.05309(17) 1.0680(3) 0.7991(3) 0.0416(10) Uani 1 1 d . . . A 1
H29 H 0.0537 1.1318 0.7999 0.050 Uiso 1 1 calc R U . A 1
C30 C 0.0000 1.0213(5) 0.7500 0.0413(15) Uani 1 2 d S T P A 1
C31 C 0.0000 0.9254(4) 0.7500 0.0335(13) Uani 1 2 d S T P A 1
C32 C 0.05332(16) 0.8784(3) 0.8013(2) 0.0364(10) Uani 1 1 d . . . A 1
C33 C 0.10380(16) 0.9269(3) 0.8463(2) 0.0390(10) Uani 1 1 d . . . A 1
H33 H 0.1395 0.8959 0.8786 0.047 Uiso 1 1 calc R U . A 1
C34 C 0.10360(18) 1.0206(3) 0.8455(3) 0.0460(11) Uani 1 1 d . . . A 1
H34 H 0.1391 1.0522 0.8776 0.055 Uiso 1 1 calc R U . A 1
C35 C 0.05324(16) 0.7782(3) 0.8042(2) 0.0353(10) Uani 1 1 d . . . A 1
C36 C 0.0000 0.7312(4) 0.7500 0.0357(13) Uani 1 2 d S T P A 1
C37 C 0.0000 0.6344(4) 0.7500 0.0375(14) Uani 1 2 d S T P A 1
C38 C 0.05218(18) 0.5875(3) 0.8052(3) 0.0468(11) Uani 1 1 d . . . A 1
H38 H 0.0524 0.5236 0.8049 0.056 Uiso 1 1 calc R U . A 1
C39 C 0.10210(17) 0.6332(3) 0.8589(3) 0.0447(11) Uani 1 1 d . . . A 1
H39 H 0.1369 0.6011 0.8970 0.054 Uiso 1 1 calc R U . A 1
C40 C 0.10274(18) 0.7288(3) 0.8586(3) 0.0457(11) Uani 1 1 d . . . A 1
H40 H 0.1382 0.7594 0.8968 0.055 Uiso 1 1 calc R 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 0.0181 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'
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'
Zn Zn -1.5491 0.6778 '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
_geom_angle_publ_flag
O4 Zn1 O1 103.81(11) . . ?
O4 Zn1 N1 112.49(11) . . ?
O1 Zn1 N1 121.66(12) . . ?
O4 Zn1 N2 120.88(12) . . ?
O1 Zn1 N2 99.36(11) . . ?
N1 Zn1 N2 99.14(11) . . ?
C21 O1 Zn1 121.4(2) . . ?
C25 O4 Zn1 117.8(2) . . ?
C1 N1 C5 118.0(3) . . ?
C1 N1 Zn1 117.9(2) . . ?
C5 N1 Zn1 122.5(3) . . ?
N1 C1 C2 122.2(3) . . ?
C1 C2 C3 119.8(3) . . ?
C4 C3 C2 117.2(3) . . ?
C4 C3 C6 119.0(3) . . ?
C2 C3 C6 123.8(4) . . ?
C5 C4 C3 119.7(3) . . ?
N1 C5 C4 123.0(4) . . ?
C7 C6 C3 125.5(4) . . ?
C6 C7 C8 125.9(3) . . ?
C9 C8 C10 118.0(3) . 5_576 ?
C9 C8 C7 118.5(3) . . ?
C10 C8 C7 123.5(3) 5_576 . ?
C8 C9 C10 121.6(3) . . ?
C9 C10 C8 120.4(3) . 5_576 ?
C11 N2 C15 117.3(3) . . ?
C11 N2 Zn1 119.9(2) . . ?
C15 N2 Zn1 121.5(2) . . ?
N2 C11 C12 122.6(3) . . ?
C11 C12 C13 120.2(3) . . ?
C12 C13 C14 117.1(3) . . ?
C12 C13 C16 120.1(3) . . ?
C14 C13 C16 122.8(3) . . ?
C15 C14 C13 119.4(3) . . ?
N2 C15 C14 123.5(3) . . ?
C17 C16 C13 125.4(3) . . ?
C16 C17 C18 127.0(3) . . ?
C19 C18 C20 117.6(3) . 5_677 ?
C19 C18 C17 119.0(3) . . ?
C20 C18 C17 123.3(3) 5_677 . ?
C20 C19 C18 121.3(3) . . ?
C19 C20 C18 121.0(3) . 5_677 ?
O1 C21 O2 124.9(3) . . ?
O1 C21 C22 117.3(3) . . ?
O2 C21 C22 117.7(3) . . ?
C24 C22 C23 120.1(3) 7_557 . ?
C24 C22 C21 118.9(3) 7_557 . ?
C23 C22 C21 121.0(3) . . ?
O3 C23 C24 118.8(4) . . ?
O3 C23 C22 122.3(3) . . ?
C24 C23 C22 118.9(3) . . ?
C22 C24 C23 121.0(4) 7_557 . ?
O4 C25 O5 125.4(3) . . ?
O4 C25 C26 118.6(3) . . ?
O5 C25 C26 116.0(3) . . ?
C28 C26 C27 119.9(3) 7_556 . ?
C28 C26 C25 117.6(3) 7_556 . ?
C27 C26 C25 122.5(3) . . ?
O6 C27 C28 118.6(3) . . ?
O6 C27 C26 122.0(3) . . ?
C28 C27 C26 119.4(3) . . ?
C27 C28 C26 120.8(3) . 7_556 ?
C34 C29 C30 119.7(5) . . ?
C29 C30 C29 121.3(6) . 2_556 ?
C29 C30 C31 119.3(3) . . ?
C29 C30 C31 119.3(3) 2_556 . ?
C32 C31 C32 121.2(6) 2_556 . ?
C32 C31 C30 119.4(3) 2_556 . ?
C32 C31 C30 119.4(3) . . ?
C33 C32 C31 119.0(4) . . ?
C33 C32 C35 121.6(4) . . ?
C31 C32 C35 119.4(4) . . ?
C32 C33 C34 121.4(4) . . ?
C29 C34 C33 121.2(4) . . ?
C40 C35 C36 118.4(4) . . ?
C40 C35 C32 122.5(4) . . ?
C36 C35 C32 119.2(4) . . ?
C35 C36 C35 121.3(6) . 2_556 ?
C35 C36 C37 119.3(3) . . ?
C35 C36 C37 119.3(3) 2_556 . ?
C38 C37 C38 120.7(6) . 2_556 ?
C38 C37 C36 119.7(3) . . ?
C38 C37 C36 119.7(3) 2_556 . ?
C39 C38 C37 120.2(5) . . ?
C38 C39 C40 120.6(4) . . ?
C35 C40 C39 121.7(4) . . ?
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
Zn1 O4 1.922(2) . ?
Zn1 O1 1.930(2) . ?
Zn1 N1 2.019(3) . ?
Zn1 N2 2.038(3) . ?
O1 C21 1.224(4) . ?
O2 C21 1.265(5) . ?
O3 C23 1.365(5) . ?
O4 C25 1.208(4) . ?
O5 C25 1.291(4) . ?
O6 C27 1.367(4) . ?
N1 C1 1.337(5) . ?
N1 C5 1.347(4) . ?
C1 C2 1.381(5) . ?
C2 C3 1.403(5) . ?
C3 C4 1.384(5) . ?
C3 C6 1.466(5) . ?
C4 C5 1.371(5) . ?
C6 C7 1.308(5) . ?
C7 C8 1.473(5) . ?
C8 C9 1.385(5) . ?
C8 C10 1.402(5) 5_576 ?
C9 C10 1.387(5) . ?
C10 C8 1.402(5) 5_576 ?
N2 C11 1.343(4) . ?
N2 C15 1.345(4) . ?
C11 C12 1.382(5) . ?
C12 C13 1.383(5) . ?
C13 C14 1.402(5) . ?
C13 C16 1.466(5) . ?
C14 C15 1.369(5) . ?
C16 C17 1.334(5) . ?
C17 C18 1.459(5) . ?
C18 C19 1.400(5) . ?
C18 C20 1.400(4) 5_677 ?
C19 C20 1.379(5) . ?
C20 C18 1.400(4) 5_677 ?
C21 C22 1.502(5) . ?
C22 C24 1.387(5) 7_557 ?
C22 C23 1.403(5) . ?
C23 C24 1.392(5) . ?
C24 C22 1.387(5) 7_557 ?
C25 C26 1.507(4) . ?
C26 C28 1.393(5) 7_556 ?
C26 C27 1.410(5) . ?
C27 C28 1.386(5) . ?
C28 C26 1.393(5) 7_556 ?
C29 C34 1.370(6) . ?
C29 C30 1.417(5) . ?
C30 C29 1.417(5) 2_556 ?
C30 C31 1.427(9) . ?
C31 C32 1.426(5) 2_556 ?
C31 C32 1.426(5) . ?
C32 C33 1.377(5) . ?
C32 C35 1.492(6) . ?
C33 C34 1.395(6) . ?
C35 C40 1.380(6) . ?
C35 C36 1.428(5) . ?
C36 C35 1.428(5) 2_556 ?
C36 C37 1.441(8) . ?
C37 C38 1.410(5) . ?
C37 C38 1.410(5) 2_556 ?
C38 C39 1.357(6) . ?
C39 C40 1.422(6) . ?
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
O3 H3 O2 0.84 1.82 2.558(4) 146.0 .
O6 H6 O5 0.84 1.83 2.574(3) 146.1 .
C1 H1 O6 0.95 2.58 3.506(4) 165.8 6_566
C5 H5 O5 0.95 2.48 3.105(5) 123.5 .
C11 H11 O1 0.95 2.55 3.116(4) 118.4 .
