#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/41/2224122.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2224122
loop_
_publ_author_name
'Guo, Wenbo'
'Liu, Xueqin'
'Li, Long'
'Deng, Dongsheng'
_publ_section_title
;
 2-Iodo-3-methoxy-6-methylpyridine
;
_journal_coeditor_code           BQ2179
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3269
_journal_paper_doi               10.1107/S1600536809050739
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C7 H8 I N O'
_chemical_formula_moiety         'C7 H8 I N O'
_chemical_formula_sum            'C7 H8 I N O'
_chemical_formula_weight         249.04
_chemical_name_systematic
;
2-Iodo-3-methoxy-6-methylpyridine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.0930(10)
_cell_angle_beta                 90.6330(10)
_cell_angle_gamma                103.6360(10)
_cell_formula_units_Z            6
_cell_length_a                   7.7974(9)
_cell_length_b                   10.8302(12)
_cell_length_c                   16.2898(18)
_cell_measurement_reflns_used    3296
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.07
_cell_measurement_theta_min      2.70
_cell_volume                     1280.2(2)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9886
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.61
_exptl_absorpt_coefficient_mu    3.687
_exptl_absorpt_correction_T_max  0.6457
_exptl_absorpt_correction_T_min  0.5259
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.938
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.680
_refine_ls_extinction_coef       0.0067(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXS97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         4737
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0291
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0183P)²+0.8733P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0563
_refine_ls_wR_factor_ref         0.0622
_reflns_number_gt                3719
_reflns_number_total             4737
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bq2179.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2224122
_cod_database_fobs_code          2224122
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2655(6) 0.5314(4) 0.5640(3) 0.0522(10) Uani d . 1 . .
C C2 0.3438(6) 0.6096(5) 0.5130(3) 0.0581(11) Uani d . 1 . .
C C3 0.3160(7) 0.5495(6) 0.4251(3) 0.0776(15) Uani d . 1 . .
H H3 0.3633 0.5957 0.3870 0.093 Uiso calc R 1 . .
C C4 0.2179(7) 0.4212(6) 0.3958(3) 0.0801(15) Uani d . 1 . .
H H4 0.2010 0.3797 0.3371 0.096 Uiso calc R 1 . .
C C5 0.1440(6) 0.3525(5) 0.4509(3) 0.0652(13) Uani d . 1 . .
C C6 0.0322(8) 0.2131(5) 0.4196(3) 0.0905(17) Uani d . 1 . .
H H6A 0.0896 0.1550 0.4380 0.136 Uiso calc R 1 . .
H H6B 0.0167 0.1866 0.3581 0.136 Uiso calc R 1 . .
H H6C -0.0813 0.2084 0.4425 0.136 Uiso calc R 1 . .
C C7 0.5208(8) 0.8131(5) 0.4975(4) 0.0900(17) Uani d . 1 . .
H H7A 0.5924 0.7653 0.4600 0.135 Uiso calc R 1 . .
H H7B 0.5938 0.8961 0.5321 0.135 Uiso calc R 1 . .
H H7C 0.4311 0.8294 0.4639 0.135 Uiso calc R 1 . .
C C8 0.5213(6) 0.3742(4) 0.0739(2) 0.0479(10) Uani d . 1 . .
C C9 0.6383(6) 0.4983(4) 0.0899(3) 0.0500(10) Uani d . 1 . .
C C10 0.5793(7) 0.6050(4) 0.1397(3) 0.0627(12) Uani d . 1 . .
H H10 0.6521 0.6906 0.1541 0.075 Uiso calc R 1 . .
C C11 0.4127(7) 0.5816(5) 0.1669(3) 0.0671(13) Uani d . 1 . .
H H11 0.3725 0.6521 0.2004 0.081 Uiso calc R 1 . .
C C12 0.3034(6) 0.4552(5) 0.1456(3) 0.0596(11) Uani d . 1 . .
C C13 0.1181(7) 0.4251(5) 0.1713(3) 0.0791(15) Uani d . 1 . .
H H13A 0.0364 0.4120 0.1233 0.119 Uiso calc R 1 . .
H H13B 0.1029 0.4979 0.2176 0.119 Uiso calc R 1 . .
H H13C 0.0959 0.3460 0.1894 0.119 Uiso calc R 1 . .
C C14 0.9152(7) 0.6345(4) 0.0738(3) 0.0765(15) Uani d . 1 . .
H H14A 0.8591 0.6908 0.0527 0.115 Uiso calc R 1 . .
H H14B 1.0216 0.6276 0.0458 0.115 Uiso calc R 1 . .
H H14C 0.9438 0.6715 0.1345 0.115 Uiso calc R 1 . .
C C15 0.1107(5) 0.9067(4) 0.2665(2) 0.0450(9) Uani d . 1 . .
C C16 0.2909(5) 0.9519(4) 0.2630(3) 0.0483(10) Uani d . 1 . .
C C17 0.3429(6) 1.0324(4) 0.2107(3) 0.0624(12) Uani d . 1 . .
H H17 0.4627 1.0660 0.2063 0.075 Uiso calc R 1 . .
C C18 0.2179(7) 1.0628(4) 0.1653(3) 0.0646(12) Uani d . 1 . .
H H18 0.2528 1.1183 0.1308 0.077 Uiso calc R 1 . .
C C19 0.0416(6) 1.0116(4) 0.1705(3) 0.0594(11) Uani d . 1 . .
C C20 -0.1023(7) 1.0386(6) 0.1207(4) 0.0880(17) Uani d . 1 . .
H H20A -0.1829 0.9561 0.0903 0.132 Uiso calc R 1 . .
H H20B -0.0505 1.0840 0.0807 0.132 Uiso calc R 1 . .
H H20C -0.1652 1.0928 0.1596 0.132 Uiso calc R 1 . .
C C21 0.5866(6) 0.9547(5) 0.3028(4) 0.0871(17) Uani d . 1 . .
H H21A 0.6098 0.9276 0.2436 0.131 Uiso calc R 1 . .
H H21B 0.6499 0.9151 0.3351 0.131 Uiso calc R 1 . .
H H21C 0.6248 1.0495 0.3247 0.131 Uiso calc R 1 . .
I I1 0.30556(5) 0.61072(3) 0.698542(19) 0.07157(13) Uani d . 1 . .
I I2 0.60344(4) 0.20520(3) 0.00399(2) 0.06819(12) Uani d . 1 . .
I I3 0.01400(4) 0.78330(3) 0.344715(19) 0.05933(11) Uani d . 1 . .
N N1 0.1683(5) 0.4079(4) 0.5349(2) 0.0568(9) Uani d . 1 . .
N N2 0.3602(5) 0.3508(3) 0.0991(2) 0.0538(9) Uani d . 1 . .
N N3 -0.0123(4) 0.9329(3) 0.2220(2) 0.0526(9) Uani d . 1 . .
O O1 0.4377(4) 0.7353(3) 0.5523(2) 0.0727(9) Uani d . 1 . .
O O2 0.7978(4) 0.5059(3) 0.05666(19) 0.0619(8) Uani d . 1 . .
O O3 0.3999(4) 0.9124(3) 0.3106(2) 0.0648(8) Uani d . 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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 125.0(4) ?
N1 C1 I1 . . 116.1(3) ?
C2 C1 I1 . . 118.9(3) ?
O1 C2 C3 . . 126.1(4) ?
O1 C2 C1 . . 118.2(4) ?
C3 C2 C1 . . 115.6(5) ?
C4 C3 C2 . . 118.8(5) ?
C4 C3 H3 . . 120.6 ?
C2 C3 H3 . . 120.6 ?
C3 C4 C5 . . 121.4(5) ?
C3 C4 H4 . . 119.3 ?
C5 C4 H4 . . 119.3 ?
N1 C5 C4 . . 120.8(5) ?
N1 C5 C6 . . 117.3(5) ?
C4 C5 C6 . . 122.0(5) ?
C5 C6 H6A . . 109.5 ?
C5 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C5 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
O1 C7 H7A . . 109.5 ?
O1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
N2 C8 C9 . . 125.6(4) ?
N2 C8 I2 . . 115.6(3) ?
C9 C8 I2 . . 118.8(3) ?
O2 C9 C8 . . 118.2(4) ?
O2 C9 C10 . . 125.8(4) ?
C8 C9 C10 . . 116.0(4) ?
C11 C10 C9 . . 118.9(4) ?
C11 C10 H10 . . 120.6 ?
C9 C10 H10 . . 120.6 ?
C10 C11 C12 . . 121.0(4) ?
C10 C11 H11 . . 119.5 ?
C12 C11 H11 . . 119.5 ?
N2 C12 C11 . . 120.6(4) ?
N2 C12 C13 . . 116.3(4) ?
C11 C12 C13 . . 123.1(4) ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
O2 C14 H14A . . 109.5 ?
O2 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
O2 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
N3 C15 C16 . . 124.5(4) ?
N3 C15 I3 . . 115.2(3) ?
C16 C15 I3 . . 120.3(3) ?
O3 C16 C17 . . 126.2(4) ?
O3 C16 C15 . . 117.2(4) ?
C17 C16 C15 . . 116.6(4) ?
C18 C17 C16 . . 119.8(4) ?
C18 C17 H17 . . 120.1 ?
C16 C17 H17 . . 120.1 ?
C19 C18 C17 . . 120.2(4) ?
C19 C18 H18 . . 119.9 ?
C17 C18 H18 . . 119.9 ?
N3 C19 C18 . . 120.8(4) ?
N3 C19 C20 . . 116.4(4) ?
C18 C19 C20 . . 122.8(4) ?
C19 C20 H20A . . 109.5 ?
C19 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C19 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
O3 C21 H21A . . 109.5 ?
O3 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
O3 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C1 N1 C5 . . 118.3(4) ?
C8 N2 C12 . . 117.8(4) ?
C15 N3 C19 . . 118.0(4) ?
C2 O1 C7 . . 116.9(4) ?
C9 O2 C14 . . 117.1(3) ?
C16 O3 C21 . . 116.5(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.323(5) ?
C1 C2 . 1.392(6) ?
C1 I1 . 2.110(4) ?
C2 O1 . 1.355(5) ?
C2 C3 . 1.390(6) ?
C3 C4 . 1.366(7) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.368(7) ?
C4 H4 . 0.9300 ?
C5 N1 . 1.324(5) ?
C5 C6 . 1.497(7) ?
C6 H6A . 0.9600 ?
C6 H6B . 0.9600 ?
C6 H6C . 0.9600 ?
C7 O1 . 1.449(5) ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 N2 . 1.315(5) ?
C8 C9 . 1.389(5) ?
C8 I2 . 2.115(4) ?
C9 O2 . 1.356(5) ?
C9 C10 . 1.394(6) ?
C10 C11 . 1.367(6) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.379(6) ?
C11 H11 . 0.9300 ?
C12 N2 . 1.348(5) ?
C12 C13 . 1.496(6) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 O2 . 1.426(5) ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 N3 . 1.324(5) ?
C15 C16 . 1.382(5) ?
C15 I3 . 2.114(4) ?
C16 O3 . 1.359(5) ?
C16 C17 . 1.380(6) ?
C17 C18 . 1.369(6) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.369(6) ?
C18 H18 . 0.9300 ?
C19 N3 . 1.357(5) ?
C19 C20 . 1.506(6) ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
C21 O3 . 1.438(5) ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C14 H14B O2 2_765 0.96 2.56 3.429(6) 151
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 O1 . . . . 179.0(4) ?
I1 C1 C2 O1 . . . . -2.2(5) ?
N1 C1 C2 C3 . . . . -0.6(7) ?
I1 C1 C2 C3 . . . . 178.2(3) ?
O1 C2 C3 C4 . . . . 179.9(5) ?
C1 C2 C3 C4 . . . . -0.5(7) ?
C2 C3 C4 C5 . . . . 1.5(8) ?
C3 C4 C5 N1 . . . . -1.3(8) ?
C3 C4 C5 C6 . . . . 178.4(5) ?
N2 C8 C9 O2 . . . . -177.6(4) ?
I2 C8 C9 O2 . . . . 2.8(5) ?
N2 C8 C9 C10 . . . . 2.5(6) ?
I2 C8 C9 C10 . . . . -177.2(3) ?
O2 C9 C10 C11 . . . . 178.5(4) ?
C8 C9 C10 C11 . . . . -1.6(6) ?
C9 C10 C11 C12 . . . . -0.4(7) ?
C10 C11 C12 N2 . . . . 1.8(7) ?
C10 C11 C12 C13 . . . . -177.9(4) ?
N3 C15 C16 O3 . . . . -177.8(3) ?
I3 C15 C16 O3 . . . . 0.7(5) ?
N3 C15 C16 C17 . . . . 1.8(6) ?
I3 C15 C16 C17 . . . . -179.7(3) ?
O3 C16 C17 C18 . . . . 179.1(4) ?
C15 C16 C17 C18 . . . . -0.4(6) ?
C16 C17 C18 C19 . . . . -1.1(7) ?
C17 C18 C19 N3 . . . . 1.5(7) ?
C17 C18 C19 C20 . . . . -178.5(5) ?
C2 C1 N1 C5 . . . . 0.8(6) ?
I1 C1 N1 C5 . . . . -178.0(3) ?
C4 C5 N1 C1 . . . . 0.1(7) ?
C6 C5 N1 C1 . . . . -179.5(4) ?
C9 C8 N2 C12 . . . . -1.1(6) ?
I2 C8 N2 C12 . . . . 178.5(3) ?
C11 C12 N2 C8 . . . . -1.1(6) ?
C13 C12 N2 C8 . . . . 178.6(4) ?
C16 C15 N3 C19 . . . . -1.5(6) ?
I3 C15 N3 C19 . . . . -180.0(3) ?
C18 C19 N3 C15 . . . . -0.3(6) ?
C20 C19 N3 C15 . . . . 179.8(4) ?
C3 C2 O1 C7 . . . . -1.8(7) ?
C1 C2 O1 C7 . . . . 178.7(4) ?
C8 C9 O2 C14 . . . . 179.8(4) ?
C10 C9 O2 C14 . . . . -0.3(6) ?
C17 C16 O3 C21 . . . . -2.6(6) ?
C15 C16 O3 C21 . . . . 177.0(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139077810
