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#$Date: 2019-11-26 07:46:50 +0200 (Tue, 26 Nov 2019) $
#$Revision: 242978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/31/4133144.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_4133144
loop_
_publ_author_name
'Kokan, Zoran'
'Chmielewski, Michał J'
_publ_section_title
;
 A Photoswitchable Heteroditopic Ion-Pair Receptor.
;
_journal_issue                   47
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16010
_journal_page_last               16014
_journal_paper_doi               10.1021/jacs.8b08689
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C20 H17 I N5 Na O2'
_chemical_formula_sum            'C20 H17 I N5 Na O2'
_chemical_formula_weight         509.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-02-20
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.006(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8614(2)
_cell_length_b                   19.3391(6)
_cell_length_c                   15.0522(4)
_cell_measurement_reflns_used    6136
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.6210
_cell_measurement_theta_min      3.7350
_cell_volume                     1977.86(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2166776000
_diffrn_orient_matrix_UB_12      0.0071867000
_diffrn_orient_matrix_UB_13      -0.0149996000
_diffrn_orient_matrix_UB_21      -0.0659740000
_diffrn_orient_matrix_UB_22      0.0358123000
_diffrn_orient_matrix_UB_23      -0.0906439000
_diffrn_orient_matrix_UB_31      0.0114821000
_diffrn_orient_matrix_UB_32      0.0707441000
_diffrn_orient_matrix_UB_33      0.0474204000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17188
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.496
_diffrn_reflns_theta_min         3.744
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    13.170
_exptl_absorpt_correction_T_max  0.807
_exptl_absorpt_correction_T_min  0.271
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_description       needle
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.704
_refine_diff_density_min         -1.472
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4053
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0301
_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)+(0.0409P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0757
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3396
_reflns_number_total             4053
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja8b08689_si_004.cif
_cod_data_source_block           2018_02_19_dt_zk-nai_k
_cod_original_cell_volume        1977.86(11)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4133144
_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.
;
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H) groups
2. Restrained distances
 N2-H2A
 0.87 with sigma of 0.02
 H3A-N3
 0.87 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.725
_oxdiff_exptl_absorpt_empirical_full_min 0.644
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C1 C 0.7450(5) 0.35514(16) 0.7889(2) 0.0161(6) Uani 1 1 d .
C2 C 0.7898(5) 0.37197(16) 0.8794(2) 0.0196(6) Uani 1 1 d .
H2 H 0.7759 0.3395 0.9237 0.024 Uiso 1 1 calc R
C3 C 0.8557(5) 0.43832(17) 0.9021(2) 0.0214(7) Uani 1 1 d .
H3 H 0.8855 0.4513 0.9619 0.026 Uiso 1 1 calc R
C4 C 0.8765(5) 0.48492(16) 0.8341(2) 0.0192(6) Uani 1 1 d .
H4 H 0.9203 0.5298 0.8472 0.023 Uiso 1 1 calc R
C5 C 0.8303(4) 0.46292(16) 0.7458(2) 0.0159(6) Uani 1 1 d .
C6 C 0.6698(5) 0.28372(16) 0.7640(2) 0.0164(6) Uani 1 1 d .
C7 C 0.5910(5) 0.20085(16) 0.6422(2) 0.0182(6) Uani 1 1 d .
H7A H 0.5072 0.2059 0.5851 0.022 Uiso 1 1 calc R
H7B H 0.5154 0.1778 0.6834 0.022 Uiso 1 1 calc R
C8 C 0.7681(5) 0.15670(15) 0.6294(2) 0.0171(6) Uani 1 1 d .
C9 C 0.9115(5) 0.14178(16) 0.7027(2) 0.0199(6) Uani 1 1 d .
H9 H 0.8961 0.1583 0.7593 0.024 Uiso 1 1 calc R
C10 C 1.0753(5) 0.10287(17) 0.6921(2) 0.0211(6) Uani 1 1 d .
H10 H 1.1716 0.0944 0.7407 0.025 Uiso 1 1 calc R
C11 C 1.0951(6) 0.07628(18) 0.6076(2) 0.0253(7) Uani 1 1 d .
H11 H 1.2035 0.0490 0.6004 0.030 Uiso 1 1 calc R
C12 C 0.9550(6) 0.09018(19) 0.5347(2) 0.0262(7) Uani 1 1 d .
H12 H 0.9685 0.0722 0.4785 0.031 Uiso 1 1 calc R
C13 C 0.7939(5) 0.13106(17) 0.5455(2) 0.0203(6) Uani 1 1 d .
H13 H 0.7018 0.1415 0.4960 0.024 Uiso 1 1 calc R
H2A H 0.670(6) 0.3001(17) 0.640(2) 0.024 Uiso 1 1 d DR
H3A H 0.749(6) 0.4536(12) 0.571(3) 0.024 Uiso 1 1 d DR
C14 C 0.8552(5) 0.51450(16) 0.6735(2) 0.0176(6) Uani 1 1 d .
C15 C 0.7406(5) 0.53324(16) 0.4423(2) 0.0183(6) Uani 1 1 d .
H15 H 0.6847 0.4909 0.4239 0.022 Uiso 1 1 calc R
C16 C 0.7615(5) 0.58926(17) 0.3772(2) 0.0175(6) Uani 1 1 d .
C17 C 0.7141(5) 0.57723(17) 0.2853(2) 0.0207(6) Uani 1 1 d .
H17 H 0.6673 0.5344 0.2640 0.025 Uiso 1 1 calc R
C18 C 0.7385(5) 0.63098(19) 0.2264(2) 0.0230(7) Uani 1 1 d .
H18 H 0.7080 0.6244 0.1648 0.028 Uiso 1 1 calc R
C19 C 0.8083(5) 0.69393(18) 0.2598(2) 0.0221(6) Uani 1 1 d .
H19 H 0.8261 0.7304 0.2215 0.027 Uiso 1 1 calc R
C20 C 0.8513(5) 0.70135(18) 0.3525(2) 0.0210(6) Uani 1 1 d .
H20 H 0.8989 0.7438 0.3749 0.025 Uiso 1 1 calc R
I1 I 0.13985(3) 0.16693(2) 0.95359(2) 0.01982(7) Uani 1 1 d .
N1 N 0.7638(4) 0.39970(13) 0.72213(17) 0.0160(5) Uani 1 1 d .
N2 N 0.6500(4) 0.26858(13) 0.67712(17) 0.0172(5) Uani 1 1 d D
N3 N 0.7843(4) 0.49559(14) 0.58784(17) 0.0173(5) Uani 1 1 d D
N4 N 0.8020(4) 0.54531(13) 0.52440(18) 0.0164(5) Uani 1 1 d .
N5 N 0.8282(4) 0.65113(14) 0.41112(18) 0.0176(5) Uani 1 1 d .
Na1 Na 0.5874(2) 0.15938(6) 0.92127(8) 0.0210(3) Uani 1 1 d .
O1 O 0.6360(4) 0.24333(12) 0.82389(15) 0.0201(5) Uani 1 1 d .
O2 O 0.9324(4) 0.57058(11) 0.69284(15) 0.0211(5) 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 0.0181 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'
I I -0.3257 6.8362 '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'
Na Na 0.1353 0.1239 '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
C2 C1 C6 118.7(3) . .
N1 C1 C2 123.4(3) . .
N1 C1 C6 117.9(3) . .
C1 C2 H2 120.8 . .
C3 C2 C1 118.5(3) . .
C3 C2 H2 120.8 . .
C2 C3 H3 120.5 . .
C4 C3 C2 118.9(3) . .
C4 C3 H3 120.5 . .
C3 C4 H4 120.9 . .
C3 C4 C5 118.3(3) . .
C5 C4 H4 120.9 . .
C4 C5 C14 117.1(3) . .
N1 C5 C4 124.0(3) . .
N1 C5 C14 118.9(3) . .
N2 C6 C1 115.6(3) . .
O1 C6 C1 119.4(3) . .
O1 C6 N2 125.0(3) . .
H7A C7 H7B 108.0 . .
C8 C7 H7A 109.3 . .
C8 C7 H7B 109.3 . .
N2 C7 H7A 109.3 . .
N2 C7 H7B 109.3 . .
N2 C7 C8 111.5(3) . .
C9 C8 C7 120.1(3) . .
C13 C8 C7 121.4(3) . .
C13 C8 C9 118.5(3) . .
C8 C9 H9 119.5 . .
C10 C9 C8 121.0(3) . .
C10 C9 H9 119.5 . .
C9 C10 H10 120.3 . .
C9 C10 C11 119.4(3) . .
C11 C10 H10 120.3 . .
C10 C11 H11 119.8 . .
C12 C11 C10 120.5(3) . .
C12 C11 H11 119.8 . .
C11 C12 H12 120.2 . .
C11 C12 C13 119.7(3) . .
C13 C12 H12 120.2 . .
C8 C13 H13 119.5 . .
C12 C13 C8 121.0(3) . .
C12 C13 H13 119.5 . .
N3 C14 C5 116.5(3) . .
O2 C14 C5 120.3(3) . .
O2 C14 N3 123.3(3) . .
C16 C15 H15 121.3 . .
N4 C15 H15 121.3 . .
N4 C15 C16 117.4(3) . .
C17 C16 C15 120.2(3) . .
N5 C16 C15 117.1(3) . .
N5 C16 C17 122.7(3) . .
C16 C17 H17 120.8 . .
C18 C17 C16 118.3(3) . .
C18 C17 H17 120.8 . .
C17 C18 H18 120.2 . .
C19 C18 C17 119.7(3) . .
C19 C18 H18 120.2 . .
C18 C19 H19 121.0 . .
C18 C19 C20 118.1(3) . .
C20 C19 H19 121.0 . .
C19 C20 H20 118.0 . .
N5 C20 C19 124.0(3) . .
N5 C20 H20 118.0 . .
C5 N1 C1 116.9(3) . .
C6 N2 C7 122.8(3) . .
C6 N2 H2A 119(3) . .
C7 N2 H2A 118(3) . .
C14 N3 H3A 124(3) . .
C14 N3 N4 114.6(3) . .
N4 N3 H3A 120(3) . .
C15 N4 N3 119.9(3) . .
C15 N4 Na1 122.6(2) . 2_656
N3 N4 Na1 117.02(19) . 2_656
C16 N5 Na1 116.9(2) . 2_656
C20 N5 C16 117.2(3) . .
C20 N5 Na1 125.8(2) . 2_656
N4 Na1 I1 104.63(8) 2_646 .
N4 Na1 N5 65.69(9) 2_646 2_646
N5 Na1 I1 86.65(7) 2_646 .
O1 Na1 I1 107.55(8) . .
O1 Na1 N4 143.79(11) . 2_646
O1 Na1 N5 131.86(10) . 2_646
O1 Na1 O2 92.78(9) . 2_646
O2 Na1 I1 100.45(8) 2_646 .
O2 Na1 N4 65.15(9) 2_646 2_646
O2 Na1 N5 130.53(10) 2_646 2_646
C6 O1 Na1 172.7(2) . .
C14 O2 Na1 118.7(2) . 2_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.393(4) .
C1 C6 1.503(4) .
C1 N1 1.344(4) .
C2 H2 0.9300 .
C2 C3 1.387(4) .
C3 H3 0.9300 .
C3 C4 1.386(4) .
C4 H4 0.9300 .
C4 C5 1.389(4) .
C5 C14 1.504(4) .
C5 N1 1.336(4) .
C6 N2 1.329(4) .
C6 O1 1.239(4) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C7 C8 1.519(4) .
C7 N2 1.448(4) .
C8 C9 1.402(4) .
C8 C13 1.391(4) .
C9 H9 0.9300 .
C9 C10 1.380(5) .
C10 H10 0.9300 .
C10 C11 1.395(5) .
C11 H11 0.9300 .
C11 C12 1.382(5) .
C12 H12 0.9300 .
C12 C13 1.387(5) .
C13 H13 0.9300 .
C14 N3 1.362(4) .
C14 O2 1.224(4) .
C15 H15 0.9300 .
C15 C16 1.481(4) .
C15 N4 1.270(4) .
C16 C17 1.396(4) .
C16 N5 1.355(4) .
C17 H17 0.9300 .
C17 C18 1.391(4) .
C18 H18 0.9300 .
C18 C19 1.377(5) .
C19 H19 0.9300 .
C19 C20 1.393(5) .
C20 H20 0.9300 .
C20 N5 1.336(4) .
I1 Na1 3.1788(15) .
N2 H2A 0.851(19) .
N3 H3A 0.872(19) .
N3 N4 1.372(3) .
N4 Na1 2.437(3) 2_656
N5 Na1 2.514(3) 2_656
Na1 N4 2.437(3) 2_646
Na1 N5 2.514(3) 2_646
Na1 O1 2.243(3) .
Na1 O2 2.419(3) 2_646
O2 Na1 2.419(3) 2_656
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_4
C1 C2 C3 C4 -0.7(5) .
C1 C6 N2 C7 176.1(3) .
C2 C1 C6 N2 -173.1(3) .
C2 C1 C6 O1 5.1(5) .
C2 C1 N1 C5 0.4(5) .
C2 C3 C4 C5 -0.1(5) .
C3 C4 C5 C14 -179.7(3) .
C3 C4 C5 N1 1.1(5) .
C4 C5 C14 N3 -171.3(3) .
C4 C5 C14 O2 7.4(5) .
C4 C5 N1 C1 -1.3(5) .
C5 C14 N3 N4 177.2(3) .
C5 C14 O2 Na1 -168.4(2) 2_656
C6 C1 C2 C3 -178.8(3) .
C6 C1 N1 C5 179.8(3) .
C7 C8 C9 C10 -178.7(3) .
C7 C8 C13 C12 -179.3(3) .
C8 C7 N2 C6 -95.6(4) .
C8 C9 C10 C11 -2.0(5) .
C9 C8 C13 C12 1.6(5) .
C9 C10 C11 C12 1.7(5) .
C10 C11 C12 C13 0.2(6) .
C11 C12 C13 C8 -1.9(6) .
C13 C8 C9 C10 0.3(5) .
C14 C5 N1 C1 179.6(3) .
C14 N3 N4 C15 -179.9(3) .
C14 N3 N4 Na1 -7.8(3) 2_656
C15 C16 C17 C18 -179.1(3) .
C15 C16 N5 C20 178.6(3) .
C15 C16 N5 Na1 1.4(4) 2_656
C16 C15 N4 N3 179.3(3) .
C16 C15 N4 Na1 7.6(4) 2_656
C16 C17 C18 C19 0.1(5) .
C17 C16 N5 C20 -1.2(5) .
C17 C16 N5 Na1 -178.4(2) 2_656
C17 C18 C19 C20 -0.3(5) .
C18 C19 C20 N5 -0.3(5) .
C19 C20 N5 C16 1.0(5) .
C19 C20 N5 Na1 177.9(2) 2_656
N1 C1 C2 C3 0.6(5) .
N1 C1 C6 N2 7.5(4) .
N1 C1 C6 O1 -174.3(3) .
N1 C5 C14 N3 7.9(4) .
N1 C5 C14 O2 -173.4(3) .
N2 C7 C8 C9 59.1(4) .
N2 C7 C8 C13 -120.0(3) .
N3 C14 O2 Na1 10.2(4) 2_656
N4 C15 C16 C17 174.0(3) .
N4 C15 C16 N5 -5.8(4) .
N5 C16 C17 C18 0.7(5) .
O1 C6 N2 C7 -2.0(5) .
O2 C14 N3 N4 -1.5(5) .
