#------------------------------------------------------------------------------
#$Date: 2022-07-27 00:55:19 +0300 (Wed, 27 Jul 2022) $
#$Revision: 276944 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/04/7130410.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_7130410
loop_
_publ_author_name
'Abeysekera, Amila M.'
'Averkiev, Boris B.'
'Sinha, Abhijeet Shekhar'
'Aakeröy, Christer'
_publ_section_title
;
 Evaluating structure-property relationship in a new family of
 mechanically flexible co-crystals
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02047E
_journal_year                    2022
_chemical_formula_moiety         'C8 H9 I N2 O, C7 H6 O2'
_chemical_formula_sum            'C15 H15 I N2 O3'
_chemical_formula_weight         398.19
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-12
_audit_creation_method
;
APEX2 v2014.11-0
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-02-14 deposited with the CCDC.	2022-07-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.025(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2075(8)
_cell_length_b                   4.9292(3)
_cell_length_c                   22.1266(12)
_cell_measurement_reflns_used    6383
_cell_measurement_temperature    200.(2)
_cell_measurement_theta_max      68.15
_cell_measurement_theta_min      3.70
_cell_volume                     1549.56(15)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker MicroStar'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      200.(2)
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker MicroStar'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10580
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_reflns_theta_max         68.40
_diffrn_reflns_theta_min         3.70
_exptl_absorpt_coefficient_mu    16.344
_exptl_absorpt_correction_T_max  0.42
_exptl_absorpt_correction_T_min  0.14
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1250 before and 0.0714 after correction.
The Ratio of minimum to maximum transmission is 0.5071.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.796
_refine_diff_density_min         -1.147
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2742
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0402
_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)+(0.0670P)²+0.8861P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1075
_reflns_number_gt                2488
_reflns_number_total             2742
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc02047e2.cif
_cod_data_source_block           I-Et_BA
_cod_database_code               7130410
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_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_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4329(3) -0.0224(7) 0.58792(18) 0.0319(8) Uani d . . . 1 . .
N N2 0.3672(2) 0.1584(6) 0.60415(14) 0.0342(7) Uani d . . . 1 . .
C C3 0.2862(3) 0.1676(8) 0.57358(17) 0.0353(8) Uani d . . . 1 . .
H H3 0.2399 0.2965 0.5852 0.042 Uiso calc U . R 1 . .
C C4 0.2676(3) -0.0027(7) 0.52598(19) 0.0337(8) Uani d . . . 1 . .
C C5 0.3346(3) -0.1913(8) 0.50902(17) 0.0381(8) Uani d . . . 1 . .
H H5 0.3232 -0.3113 0.4762 0.046 Uiso calc U . R 1 . .
C C6 0.4176(3) -0.2022(8) 0.54014(16) 0.0364(8) Uani d . . . 1 . .
H H6 0.4645 -0.3309 0.5294 0.044 Uiso calc U . R 1 . .
I I7 0.13927(2) 0.03010(6) 0.47969(2) 0.04749(15) Uani d . . . 1 . .
H H8 0.517(3) 0.108(10) 0.648(2) 0.041(12) Uiso d . . . 1 . .
N N8 0.5137(3) -0.0104(6) 0.62229(17) 0.0340(7) Uani d . . . 1 . .
C C9 0.5919(2) -0.1769(7) 0.61962(16) 0.0335(8) Uani d . . . 1 . .
O O10 0.5981(2) -0.3681(6) 0.58556(13) 0.0452(7) Uani d . . . 1 . .
C C11 0.6692(3) -0.0926(8) 0.66240(19) 0.0394(9) Uani d . . . 1 . .
H H11A 0.7046 0.06 0.6443 0.047 Uiso calc U . R 1 . .
H H11B 0.6406 -0.027 0.7005 0.047 Uiso calc U . R 1 . .
C C12 0.7367(3) -0.3193(9) 0.6767(2) 0.0465(10) Uani d . . . 1 . .
H H12A 0.7614 -0.3955 0.639 0.07 Uiso calc U . R 1 . .
H H12B 0.7038 -0.4612 0.6994 0.07 Uiso calc U . R 1 . .
H H12C 0.7889 -0.2485 0.701 0.07 Uiso calc U . R 1 . .
C C13 0.4412(2) -0.2488(7) 0.77424(15) 0.0273(7) Uani d . . . 1 . .
C C14 0.5171(2) -0.2232(8) 0.81312(17) 0.0361(8) Uani d . . . 1 . .
H H14 0.5708 -0.3357 0.8081 0.043 Uiso calc U . R 1 . .
C C15 0.5149(3) -0.0349(8) 0.8591(2) 0.0426(10) Uani d . . . 1 . .
H H15 0.5672 -0.0176 0.8857 0.051 Uiso calc U . R 1 . .
C C16 0.4364(3) 0.1299(9) 0.86687(18) 0.0407(9) Uani d . . . 1 . .
H H16 0.4347 0.2582 0.8989 0.049 Uiso calc U . R 1 . .
C C17 0.3610(3) 0.1066(8) 0.82792(18) 0.0367(8) Uani d . . . 1 . .
H H17 0.3078 0.2211 0.8328 0.044 Uiso calc U . R 1 . .
C C18 0.3626(2) -0.0834(7) 0.78165(17) 0.0310(7) Uani d . . . 1 . .
H H18 0.3103 -0.1006 0.7551 0.037 Uiso calc U . R 1 . .
C C19 0.4453(3) -0.4536(7) 0.72502(18) 0.0295(8) Uani d . . . 1 . .
O O20 0.51521(18) -0.5940(6) 0.71571(13) 0.0377(6) Uani d . . . 1 . .
H H21 0.368(3) -0.601(10) 0.666(2) 0.051(14) Uiso d . . . 1 . .
O O21 0.3679(2) -0.4704(5) 0.69251(14) 0.0375(6) 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 0.0181 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 N8 . . 113.8(3) ?
N2 C1 C6 . . 121.1(4) ?
N8 C1 C6 . . 125.1(3) ?
C3 N2 C1 . . 119.2(3) ?
N2 C3 C4 . . 122.2(3) ?
N2 C3 H3 . . 118.9 ?
C4 C3 H3 . . 118.9 ?
C3 C4 C5 . . 119.1(4) ?
C3 C4 I7 . . 119.6(3) ?
C5 C4 I7 . . 121.2(3) ?
C6 C5 C4 . . 119.0(3) ?
C6 C5 H5 . . 120.5 ?
C4 C5 H5 . . 120.5 ?
C5 C6 C1 . . 119.4(3) ?
C5 C6 H6 . . 120.3 ?
C1 C6 H6 . . 120.3 ?
C4 I7 I7 . 3_556 137.04(11) ?
C1 N8 C9 . . 128.3(3) ?
C1 N8 H8 . . 118.(3) ?
C9 N8 H8 . . 114.(3) ?
O10 C9 N8 . . 123.2(4) ?
O10 C9 C11 . . 123.6(3) ?
N8 C9 C11 . . 113.2(3) ?
C12 C11 C9 . . 113.0(3) ?
C12 C11 H11A . . 109.0 ?
C9 C11 H11A . . 109.0 ?
C12 C11 H11B . . 109.0 ?
C9 C11 H11B . . 109.0 ?
H11A C11 H11B . . 107.8 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C14 C13 C18 . . 119.9(3) ?
C14 C13 C19 . . 119.1(3) ?
C18 C13 C19 . . 121.0(3) ?
C15 C14 C13 . . 120.2(4) ?
C15 C14 H14 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
C14 C15 C16 . . 120.2(4) ?
C14 C15 H15 . . 119.9 ?
C16 C15 H15 . . 119.9 ?
C17 C16 C15 . . 119.8(4) ?
C17 C16 H16 . . 120.1 ?
C15 C16 H16 . . 120.1 ?
C16 C17 C18 . . 120.3(4) ?
C16 C17 H17 . . 119.9 ?
C18 C17 H17 . . 119.9 ?
C17 C18 C13 . . 119.7(3) ?
C17 C18 H18 . . 120.2 ?
C13 C18 H18 . . 120.2 ?
O20 C19 O21 . . 123.3(3) ?
O20 C19 C13 . . 122.5(4) ?
O21 C19 C13 . . 114.2(3) ?
C19 O21 H21 . . 115.(3) ?
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 N2 . 1.340(5) ?
C1 N8 . 1.378(6) ?
C1 C6 . 1.396(5) ?
N2 C3 . 1.336(5) ?
C3 C4 . 1.373(6) ?
C3 H3 . 0.95 ?
C4 C5 . 1.383(5) ?
C4 I7 . 2.097(4) ?
C5 C6 . 1.366(5) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
I7 I7 3_556 4.0693(6) ?
N8 C9 . 1.383(5) ?
N8 H8 . 0.82(5) ?
C9 O10 . 1.210(5) ?
C9 C11 . 1.508(5) ?
C11 C12 . 1.506(6) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 C14 . 1.384(5) ?
C13 C18 . 1.392(5) ?
C13 C19 . 1.487(5) ?
C14 C15 . 1.378(6) ?
C14 H14 . 0.95 ?
C15 C16 . 1.390(6) ?
C15 H15 . 0.95 ?
C16 C17 . 1.379(6) ?
C16 H16 . 0.95 ?
C17 C18 . 1.388(6) ?
C17 H17 . 0.95 ?
C18 H18 . 0.95 ?
C19 O20 . 1.228(5) ?
C19 O21 . 1.317(5) ?
O21 H21 . 0.88(5) ?
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
_geom_hbond_publ_flag
N8 H8 O20 1_565 0.82(5) 2.09(5) 2.913(4) 176.(4) ?
O21 H21 N2 1_545 0.88(5) 1.81(5) 2.678(4) 174.(5) ?
