#------------------------------------------------------------------------------
#$Date: 2016-02-05 00:32:49 +0200 (Fri, 05 Feb 2016) $
#$Revision: 175970 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/36/7223614.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_7223614
loop_
_publ_author_name
'Puttreddy, Rakesh'
'Beyeh, Ngong Kodiah'
'Rissanen, Kari'
_publ_section_title
;
 Inclusion complexes of Cethyl-2-methylresorcinarene and pyridine
 N-oxides: breaking the C--I⋯−O--N+halogen bond by
 host--guest complexation
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              793
_journal_paper_doi               10.1039/C5CE02354H
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C5 H4 I N O'
_chemical_formula_sum            'C5 H4 I N O'
_chemical_formula_weight         220.99
_chemical_name_systematic
;
 ?
;
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-10-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2015-12-17 deposited with the CCDC.
2015-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.672(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3971(2)
_cell_length_b                   8.3248(3)
_cell_length_c                   9.1806(3)
_cell_measurement_reflns_used    1677
_cell_measurement_temperature    123
_cell_measurement_theta_max      28.6510
_cell_measurement_theta_min      3.4330
_cell_volume                     641.49(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0053
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -59.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368   19.0000 -120.0000 113

  2 omega   16.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       19.3868   57.0000   30.0000 50

  3 omega    9.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       19.3868  -99.0000  -60.0000 51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0542372000
_diffrn_orient_matrix_UB_12      -0.0558178000
_diffrn_orient_matrix_UB_13      -0.0293418000
_diffrn_orient_matrix_UB_21      0.0369937000
_diffrn_orient_matrix_UB_22      0.0630968000
_diffrn_orient_matrix_UB_23      -0.0383792000
_diffrn_orient_matrix_UB_31      0.0532274000
_diffrn_orient_matrix_UB_32      0.0130264000
_diffrn_orient_matrix_UB_33      0.0602770000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_laue_measured_fraction_full 0.996
_diffrn_reflns_laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2242
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.243
_diffrn_reflns_theta_min         3.304
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.890
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58196
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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    2.288
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.3613
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.1215
_refine_diff_density_max         0.944
_refine_diff_density_min         -0.873
_refine_diff_density_rms         0.196
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0278
_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)+(0.0339P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0724
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1001
_reflns_number_total             1149
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ce02354h2.cif
_cod_data_source_block           2IPyNO
_cod_depositor_comments
'Adding full bibliography for 7223614--7223619.cif.'
_cod_database_code               7223614
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C5 H4 N1 O1 I1'
_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 99.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
;
_shelx_res_file
;
TITL 2IPyNO_11.12.2014_gau in P21/n
CELL 0.71073 8.397081 8.32479 9.180581 90 91.6718 90
ZERR 4 0.000248 0.000271 0.000272 0 0.0029 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H I N O
UNIT 20 16 4 4 4

L.S. 4 0 0
PLAN  20
TEMP -153.15
BOND $H
fmap 2 53
acta
OMIT -3 50.5
REM <olex2.extras>
REM <HklSrc "%.\\2IPyNO_11.12.2014_gau.hkl">
REM </olex2.extras>

WGHT    0.033900
FVAR       6.27906
I1    3   -0.175316    0.873747    0.367589    11.00000    0.01626    0.01390 =
         0.01627   -0.00171   -0.00288    0.00201
O1    5   -0.108665    0.628371    0.126931    11.00000    0.01708    0.02106 =
         0.01484   -0.00218   -0.00705   -0.00146
N1    4   -0.000284    0.603423    0.232956    11.00000    0.01515    0.01067 =
         0.01313   -0.00113   -0.00242   -0.00368
C2    1    0.111148    0.487512    0.216473    11.00000    0.01977    0.01819 =
         0.01520   -0.00084    0.00388    0.00345
AFIX  43
H2    2    0.108898    0.422531    0.131373    11.00000   -1.20000
AFIX   0
C3    1    0.227016    0.464059    0.322518    11.00000    0.01825    0.02088 =
         0.02378    0.00072    0.00443    0.00349
AFIX  43
H3    2    0.304443    0.382318    0.310338    11.00000   -1.20000
AFIX   0
C4    1    0.232893    0.557429    0.446749    11.00000    0.01320    0.01916 =
         0.01833    0.00376   -0.00340    0.00117
AFIX  43
H4    2    0.313760    0.541529    0.519857    11.00000   -1.20000
AFIX   0
C5    1    0.118233    0.674510    0.462021    11.00000    0.01668    0.01530 =
         0.01650   -0.00024   -0.00014   -0.00568
AFIX  43
H5    2    0.120635    0.740774    0.546304    11.00000   -1.20000
AFIX   0
C6    1    0.000516    0.696308    0.356548    11.00000    0.01450    0.01171 =
         0.01666    0.00329   -0.00013   -0.00118
HKLF 4

REM  2IPyNO_11.12.2014_gau in P21/n
REM R1 =  0.0278 for    1001 Fo > 4sig(Fo)  and  0.0313 for all    1149 data
REM     73 parameters refined using      0 restraints

END

WGHT      0.0339      0.0000

REM Highest difference peak  0.944,  deepest hole -0.873,  1-sigma level  0.196
Q1    1  -0.2735  0.8824  0.4173  11.00000  0.05    0.94
Q2    1   0.1590  0.7103  0.5046  11.00000  0.05    0.76
Q3    1  -0.0848  0.8808  0.3006  11.00000  0.05    0.74
Q4    1  -0.2338  0.8771  0.2589  11.00000  0.05    0.63
Q5    1  -0.1357  0.7061  0.4563  11.00000  0.05    0.61
Q6    1   0.1152  0.5761  0.4865  11.00000  0.05    0.61
Q7    1   0.0000  0.5000  0.0000  10.50000  0.05    0.59
Q8    1   0.1612  0.4931  0.5368  11.00000  0.05    0.58
Q9    1   0.2907  0.3249  0.5164  11.00000  0.05    0.53
Q10   1  -0.1226  0.9383  0.4493  11.00000  0.05    0.52
Q11   1   0.2851  0.4400  0.5037  11.00000  0.05    0.52
Q12   1  -0.2134  0.6082  0.0014  11.00000  0.05    0.52
Q13   1  -0.0466  0.5816  0.5052  11.00000  0.05    0.51
Q14   1  -0.0186  0.6442  0.3007  11.00000  0.05    0.50
Q15   1   0.3898  0.4407  0.2171  11.00000  0.05    0.50
Q16   1  -0.1013  1.0239  0.2847  11.00000  0.05    0.48
Q17   1  -0.1906  0.9804  0.5070  11.00000  0.05    0.47
Q18   1  -0.1048  0.7781  0.0712  11.00000  0.05    0.47
Q19   1  -0.1344  0.8293  0.4548  11.00000  0.05    0.47
Q20   1  -0.0132  0.6343  0.0410  11.00000  0.05    0.47
;
_shelx_res_checksum              144
_olex2_submission_special_instructions 'No special instructions were received'
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
I1 I -0.17532(3) 0.87375(3) 0.36759(3) 0.01554(15) Uani 1 1 d .
O1 O -0.1087(4) 0.6284(3) 0.1269(4) 0.0178(8) Uani 1 1 d .
N1 N -0.0003(5) 0.6034(4) 0.2330(4) 0.0130(8) Uani 1 1 d .
C2 C 0.1111(5) 0.4875(6) 0.2165(5) 0.0177(10) Uani 1 1 d .
H2 H 0.1089 0.4225 0.1314 0.021 Uiso 1 1 calc R
C3 C 0.2270(6) 0.4641(6) 0.3225(5) 0.0209(11) Uani 1 1 d .
H3 H 0.3044 0.3823 0.3103 0.025 Uiso 1 1 calc R
C4 C 0.2329(5) 0.5574(5) 0.4467(5) 0.0170(10) Uani 1 1 d .
H4 H 0.3138 0.5415 0.5199 0.020 Uiso 1 1 calc R
C5 C 0.1182(5) 0.6745(6) 0.4620(5) 0.0162(10) Uani 1 1 d .
H5 H 0.1206 0.7408 0.5463 0.019 Uiso 1 1 calc R
C6 C 0.0005(5) 0.6963(5) 0.3565(5) 0.0143(10) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.0163(2) 0.0139(2) 0.0163(2) -0.00171(11) -0.00288(15) 0.00201(10)
O1 0.0171(18) 0.021(2) 0.0148(18) -0.0022(13) -0.0070(15) -0.0015(13)
N1 0.015(2) 0.0107(19) 0.013(2) -0.0011(15) -0.0024(17) -0.0037(15)
C2 0.020(3) 0.018(2) 0.015(2) -0.001(2) 0.004(2) 0.0034(19)
C3 0.018(2) 0.021(3) 0.024(3) 0.001(2) 0.004(2) 0.003(2)
C4 0.013(2) 0.019(3) 0.018(2) 0.004(2) -0.0034(19) 0.001(2)
C5 0.017(2) 0.015(2) 0.017(2) 0.000(2) 0.000(2) -0.0057(19)
C6 0.015(2) 0.012(2) 0.017(2) 0.0033(19) -0.0001(19) -0.0012(19)
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'
I I -0.4742 1.8119 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 -9 -8 0.0991 -0.0415 -8.9834 -8.0429 0.7352 -0.2597 -0.6040
2 8 9 0.1196 2.0339 7.9828 9.0430 -0.6006 0.2319 0.7573
8 -9 1 0.1163 7.9458 -8.9918 0.9823 0.9040 -0.3111 0.3650
-7 9 0 0.0986 -6.9473 8.9906 0.0203 -0.8792 0.3095 -0.2514
-8 -6 8 0.0475 -8.0286 -5.9630 8.0393 -0.3385 -0.9818 -0.0204
7 6 -9 0.0592 7.0301 5.9641 -9.0419 0.3137 0.9834 -0.0931
10 5 2 0.1335 10.0155 4.9695 1.9983 0.2072 0.6074 0.7183
-7 -2 -10 0.1739 -6.9979 -1.9892 -10.0331 0.0259 0.0007 -1.0032
5 1 11 0.1671 4.9939 0.9964 11.0393 -0.1087 -0.1761 0.9442
-5 10 4 0.0644 -4.9464 9.9874 4.0350 -0.9441 0.2923 0.1100
-6 -10 -1 0.0706 -6.0455 -9.9637 -1.0056 0.2578 -0.8137 -0.5122
5 11 -2 0.0700 5.0534 10.9608 -2.0043 -0.2789 0.9555 0.2909
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 N1 C2 119.3(4)
O1 N1 C6 120.3(4)
C2 N1 C6 120.4(4)
N1 C2 H2 120.0
N1 C2 C3 120.0(4)
C3 C2 H2 120.0
C2 C3 H3 119.5
C2 C3 C4 121.0(4)
C4 C3 H3 119.5
C3 C4 H4 120.9
C3 C4 C5 118.3(4)
C5 C4 H4 120.9
C4 C5 H5 119.6
C6 C5 C4 120.7(4)
C6 C5 H5 119.6
N1 C6 I1 116.8(3)
N1 C6 C5 119.6(4)
C5 C6 I1 123.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C6 2.093(5)
O1 N1 1.329(5)
N1 C2 1.356(6)
N1 C6 1.373(6)
C2 H2 0.9500
C2 C3 1.370(6)
C3 H3 0.9500
C3 C4 1.380(6)
C4 H4 0.9500
C4 C5 1.380(7)
C5 H5 0.9500
C5 C6 1.375(6)
