#------------------------------------------------------------------------------
#$Date: 2022-11-07 07:36:51 +0200 (Mon, 07 Nov 2022) $
#$Revision: 279002 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/19/7061919.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_7061919
loop_
_publ_author_name
'Purushotham, Manasa'
'Paul, Bishwajit'
'Gajula, Siva Nageswara Rao'
'Sahariah, Biswajit'
'Sonti, Rajesh'
_publ_section_title
;
 Deciphering C--H⋯O/X weak hydrogen bonding and halogen bonding
 interactions in aromatic peptoids
;
_journal_issue                   41
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              19648
_journal_page_last               19657
_journal_paper_doi               10.1039/D2NJ02616C
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C19 H19 I N2 O4'
_chemical_formula_sum            'C19 H19 I N2 O4'
_chemical_formula_weight         466.26
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-01-22 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                74.064(3)
_cell_angle_beta                 88.893(3)
_cell_angle_gamma                71.669(3)
_cell_formula_units_Z            2
_cell_length_a                   8.7203(5)
_cell_length_b                   9.1769(7)
_cell_length_c                   13.4991(9)
_cell_measurement_reflns_used    6941
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      56.602
_cell_measurement_theta_min      4.875
_cell_volume                     983.38(12)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altornare et al., 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10764
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.368
_diffrn_reflns_theta_min         2.438
_exptl_absorpt_coefficient_mu    1.653
_exptl_absorpt_correction_T_max  0.733
_exptl_absorpt_correction_T_min  0.595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.838
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       0.0216(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         4784
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0309
_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)+(0.0451P)²+0.6109P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0867
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4164
_reflns_number_total             4784
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj02616c2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7061918--7061922.cif.'
_cod_database_code               7061919
_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   0.595
_shelx_estimated_absorpt_t_max   0.733
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.2048(5) 0.7195(5) 0.5092(2) 0.0596(8) Uani 1 1 d . . . . .
H1 H 0.1168 0.6936 0.4904 0.071 Uiso 1 1 calc R U . . .
C2 C 0.2097(5) 0.7545(5) 0.6021(3) 0.0685(10) Uani 1 1 d . . . . .
H2 H 0.1255 0.7518 0.6451 0.082 Uiso 1 1 calc R U . . .
C3 C 0.3382(5) 0.7930(5) 0.6308(2) 0.0649(9) Uani 1 1 d . . . . .
H3 H 0.3413 0.8164 0.6934 0.078 Uiso 1 1 calc R U . . .
C4 C 0.4631(4) 0.7974(4) 0.5671(2) 0.0530(7) Uani 1 1 d . . . . .
H4 H 0.5501 0.8244 0.5862 0.064 Uiso 1 1 calc R U . . .
C5 C 0.4581(3) 0.7612(3) 0.47418(19) 0.0396(5) Uani 1 1 d . . . . .
C6 C 0.3289(4) 0.7221(3) 0.4435(2) 0.0419(6) Uani 1 1 d . . . . .
C7 C 0.3246(4) 0.6836(4) 0.3412(2) 0.0483(7) Uani 1 1 d . . . . .
H7A H 0.3569 0.7615 0.2883 0.058 Uiso 1 1 calc R U . . .
H7B H 0.4031 0.5792 0.3472 0.058 Uiso 1 1 calc R U . . .
C8 C 0.0815(5) 0.9733(4) 0.2303(3) 0.0696(10) Uani 1 1 d . . . . .
H8A H -0.0146 1.0591 0.1981 0.104 Uiso 1 1 calc R U . . .
H8B H 0.1658 0.9690 0.1833 0.104 Uiso 1 1 calc R U . . .
H8C H 0.1159 0.9912 0.2918 0.104 Uiso 1 1 calc R U . . .
C9 C 0.0461(4) 0.8179(4) 0.2578(2) 0.0452(6) Uani 1 1 d . . . . .
C10 C 0.1314(4) 0.5331(4) 0.3383(2) 0.0489(7) Uani 1 1 d . . . . .
H10A H 0.0197 0.5553 0.3561 0.059 Uiso 1 1 calc R U . . .
H10B H 0.1993 0.4646 0.4002 0.059 Uiso 1 1 calc R U . . .
C11 C 0.1555(4) 0.4409(3) 0.2589(2) 0.0451(6) Uani 1 1 d . . . . .
C12 C 0.2152(3) 0.4678(3) 0.0755(2) 0.0401(5) Uani 1 1 d . . . . .
C13 C 0.2707(3) 0.5583(3) -0.0097(2) 0.0433(6) Uani 1 1 d . . . . .
C14 C 0.2838(4) 0.5142(4) -0.1013(3) 0.0577(8) Uani 1 1 d . . . . .
H14 H 0.3239 0.5714 -0.1578 0.069 Uiso 1 1 calc R U . . .
C15 C 0.2377(5) 0.3862(5) -0.1089(3) 0.0686(10) Uani 1 1 d . . . . .
H15 H 0.2458 0.3579 -0.1704 0.082 Uiso 1 1 calc R U . . .
C16 C 0.1810(5) 0.3028(4) -0.0264(3) 0.0650(9) Uani 1 1 d . . . . .
H16 H 0.1482 0.2184 -0.0325 0.078 Uiso 1 1 calc R U . . .
C17 C 0.1699(4) 0.3387(4) 0.0669(3) 0.0544(7) Uani 1 1 d . . . . .
H17 H 0.1329 0.2777 0.1232 0.065 Uiso 1 1 calc R U . . .
C18 C 0.3103(3) 0.7025(3) -0.0063(2) 0.0454(6) Uani 1 1 d . . . . .
C19 C 0.4127(5) 0.9067(4) -0.0956(3) 0.0672(9) Uani 1 1 d . . . . .
H19A H 0.3151 0.9966 -0.1077 0.101 Uiso 1 1 calc R U . . .
H19B H 0.4817 0.9249 -0.1507 0.101 Uiso 1 1 calc R U . . .
H19C H 0.4678 0.8935 -0.0312 0.101 Uiso 1 1 calc R U . . .
N1 N 0.1666(3) 0.6833(3) 0.30847(17) 0.0428(5) Uani 1 1 d . . . . .
N2 N 0.2004(3) 0.5123(3) 0.16747(18) 0.0427(5) Uani 1 1 d . . . . .
O1 O -0.0845(3) 0.8108(3) 0.23411(19) 0.0595(6) Uani 1 1 d . . . . .
O2 O 0.2889(4) 0.7611(3) 0.06495(19) 0.0684(7) Uani 1 1 d . . . . .
O3 O 0.3728(3) 0.7641(3) -0.09129(16) 0.0575(5) Uani 1 1 d . . . . .
O4 O 0.1330(4) 0.3124(3) 0.2819(2) 0.0758(8) Uani 1 1 d . . . . .
I1 I 0.65092(2) 0.77240(2) 0.37991(2) 0.05087(10) Uani 1 1 d . . . . .
H2N H 0.209(4) 0.597(4) 0.158(3) 0.044(8) Uiso 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 0.0033 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'
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'
I I -0.4742 1.8119 '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
C2 C1 C6 121.2(3) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 I1 117.6(2) . . ?
C6 C5 I1 121.07(19) . . ?
C5 C6 C1 117.8(2) . . ?
C5 C6 C7 120.7(2) . . ?
C1 C6 C7 121.5(3) . . ?
N1 C7 C6 113.9(2) . . ?
N1 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
N1 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 N1 120.6(3) . . ?
O1 C9 C8 121.6(3) . . ?
N1 C9 C8 117.8(3) . . ?
N1 C10 C11 116.5(2) . . ?
N1 C10 H10A 108.2 . . ?
C11 C10 H10A 108.2 . . ?
N1 C10 H10B 108.2 . . ?
C11 C10 H10B 108.2 . . ?
H10A C10 H10B 107.3 . . ?
O4 C11 N2 126.0(3) . . ?
O4 C11 C10 118.6(3) . . ?
N2 C11 C10 115.4(2) . . ?
C17 C12 C13 119.8(3) . . ?
C17 C12 N2 121.0(3) . . ?
C13 C12 N2 119.2(2) . . ?
C14 C13 C12 118.9(3) . . ?
C14 C13 C18 119.3(3) . . ?
C12 C13 C18 121.8(2) . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 119.4(3) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 122.2(3) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 H16 118.9 . . ?
C16 C17 C12 119.0(3) . . ?
C16 C17 H17 120.5 . . ?
C12 C17 H17 120.5 . . ?
O2 C18 O3 122.1(3) . . ?
O2 C18 C13 125.2(3) . . ?
O3 C18 C13 112.7(3) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C9 N1 C10 118.1(2) . . ?
C9 N1 C7 123.4(3) . . ?
C10 N1 C7 118.3(3) . . ?
C11 N2 C12 129.3(2) . . ?
C11 N2 H2N 120(2) . . ?
C12 N2 H2N 110(2) . . ?
C18 O3 C19 116.6(3) . . ?
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
C1 C2 1.381(4) . ?
C1 C6 1.388(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.369(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(4) . ?
C5 I1 2.100(3) . ?
C6 C7 1.521(4) . ?
C7 N1 1.456(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.499(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 O1 1.214(4) . ?
C9 N1 1.359(4) . ?
C10 N1 1.453(4) . ?
C10 C11 1.513(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O4 1.212(4) . ?
C11 N2 1.343(4) . ?
C12 C17 1.395(4) . ?
C12 C13 1.397(4) . ?
C12 N2 1.401(3) . ?
C13 C14 1.395(4) . ?
C13 C18 1.482(4) . ?
C14 C15 1.385(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.349(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O2 1.210(4) . ?
C18 O3 1.321(4) . ?
C19 O3 1.442(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N2 H2N 0.78(3) . ?
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
C17 H17 O4 0.93 2.25 2.866(4) 123.0 .
C19 H19A O1 0.96 2.51 3.359(5) 146.9 2_575
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.1(6) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
C2 C3 C4 C5 -0.5(6) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
C3 C4 C5 I1 179.4(3) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
I1 C5 C6 C1 -179.0(2) . . . . ?
C4 C5 C6 C7 179.7(3) . . . . ?
I1 C5 C6 C7 1.0(4) . . . . ?
C2 C1 C6 C5 0.0(5) . . . . ?
C2 C1 C6 C7 179.9(3) . . . . ?
C5 C6 C7 N1 -165.9(3) . . . . ?
C1 C6 C7 N1 14.2(4) . . . . ?
N1 C10 C11 O4 177.5(3) . . . . ?
N1 C10 C11 N2 -2.7(4) . . . . ?
C17 C12 C13 C14 -1.8(4) . . . . ?
N2 C12 C13 C14 -179.4(3) . . . . ?
C17 C12 C13 C18 176.1(3) . . . . ?
N2 C12 C13 C18 -1.6(4) . . . . ?
C12 C13 C14 C15 2.1(5) . . . . ?
C18 C13 C14 C15 -175.8(3) . . . . ?
C13 C14 C15 C16 -0.6(5) . . . . ?
C14 C15 C16 C17 -1.3(6) . . . . ?
C15 C16 C17 C12 1.6(5) . . . . ?
C13 C12 C17 C16 0.0(4) . . . . ?
N2 C12 C17 C16 177.6(3) . . . . ?
C14 C13 C18 O2 172.5(3) . . . . ?
C12 C13 C18 O2 -5.3(5) . . . . ?
C14 C13 C18 O3 -7.2(4) . . . . ?
C12 C13 C18 O3 174.9(3) . . . . ?
O1 C9 N1 C10 -3.4(4) . . . . ?
C8 C9 N1 C10 178.1(3) . . . . ?
O1 C9 N1 C7 -178.6(3) . . . . ?
C8 C9 N1 C7 2.9(4) . . . . ?
C11 C10 N1 C9 87.4(3) . . . . ?
C11 C10 N1 C7 -97.2(3) . . . . ?
C6 C7 N1 C9 83.2(3) . . . . ?
C6 C7 N1 C10 -91.9(3) . . . . ?
O4 C11 N2 C12 7.4(5) . . . . ?
C10 C11 N2 C12 -172.3(3) . . . . ?
C17 C12 N2 C11 4.8(5) . . . . ?
C13 C12 N2 C11 -177.5(3) . . . . ?
O2 C18 O3 C19 -0.8(5) . . . . ?
C13 C18 O3 C19 179.0(3) . . . . ?
