#------------------------------------------------------------------------------
#$Date: 2022-11-07 07:36:51 +0200 (Mon, 07 Nov 2022) $
#$Revision: 279002 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/19/7061922.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_7061922
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 H20 N2 O4'
_chemical_formula_sum            'C19 H20 N2 O4'
_chemical_formula_weight         340.37
_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   geom
_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                101.727(12)
_cell_angle_beta                 97.628(11)
_cell_angle_gamma                104.253(13)
_cell_formula_units_Z            2
_cell_length_a                   8.4482(19)
_cell_length_b                   10.535(3)
_cell_length_c                   10.731(3)
_cell_measurement_reflns_used    1614
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      45.332
_cell_measurement_theta_min      5.797
_cell_volume                     889.4(4)
_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 0.993
_diffrn_measured_fraction_theta_max 0.959
_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  0.1196
_diffrn_reflns_av_unetI/netI     0.1138
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7437
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.479
_diffrn_reflns_theta_min         2.478
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.014(4)
_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   0.882
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.882
_refine_ls_R_factor_all          0.1213
_refine_ls_R_factor_gt           0.0611
_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)+(0.0576P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1678
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2073
_reflns_number_total             4317
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj02616c2.cif
_cod_data_source_block           shelx_CCDC4
_cod_depositor_comments
'Adding full bibliography for 7061918--7061922.cif.'
_cod_database_code               7061922
_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   0.982
_shelx_estimated_absorpt_t_max   0.987
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 1.1167(3) 0.8609(3) 0.4353(2) 0.0698(7) Uani 1 1 d . . . . .
H1 H 1.0565 0.8806 0.3663 0.084 Uiso 1 1 calc R U . . .
C2 C 1.2812(3) 0.8691(3) 0.4399(2) 0.0666(7) Uani 1 1 d . . . . .
H2 H 1.3342 0.8948 0.3747 0.080 Uiso 1 1 calc R U . . .
C3 C 1.3664(3) 0.8390(3) 0.5413(3) 0.0665(7) Uani 1 1 d . . . . .
H3 H 1.4785 0.8445 0.5451 0.080 Uiso 1 1 calc R U . . .
C4 C 1.2901(3) 0.8008(2) 0.6380(2) 0.0562(6) Uani 1 1 d . . . . .
H4 H 1.3509 0.7808 0.7065 0.067 Uiso 1 1 calc R U . . .
C5 C 1.1240(2) 0.7918(2) 0.63477(19) 0.0443(5) Uani 1 1 d . . . . .
C6 C 1.0399(3) 0.8235(3) 0.5331(2) 0.0618(7) Uani 1 1 d . . . . .
H6 H 0.9282 0.8197 0.5298 0.074 Uiso 1 1 calc R U . . .
C7 C 1.0434(2) 0.7452(2) 0.7414(2) 0.0530(6) Uani 1 1 d . . . . .
H7A H 1.0484 0.6538 0.7389 0.064 Uiso 1 1 calc R U . . .
H7B H 1.1075 0.8023 0.8244 0.064 Uiso 1 1 calc R U . . .
C8 C 0.7385(3) 0.6443(2) 0.6587(2) 0.0486(5) Uani 1 1 d . . . . .
C9 C 0.7729(3) 0.5213(2) 0.5872(2) 0.0682(7) Uani 1 1 d . . . . .
H9A H 0.7991 0.4693 0.6468 0.102 Uiso 1 1 calc R U . . .
H9B H 0.8655 0.5468 0.5455 0.102 Uiso 1 1 calc R U . . .
H9C H 0.6765 0.4681 0.5230 0.102 Uiso 1 1 calc R U . . .
C10 C 0.8402(3) 0.8704(2) 0.79687(19) 0.0503(5) Uani 1 1 d . . . . .
H10A H 0.7487 0.8844 0.7417 0.060 Uiso 1 1 calc R U . . .
H10B H 0.9377 0.9448 0.8034 0.060 Uiso 1 1 calc R U . . .
C11 C 0.7992(2) 0.8779(2) 0.9304(2) 0.0461(5) Uani 1 1 d . . . . .
C12 C 0.7403(2) 0.7335(2) 1.08516(19) 0.0434(5) Uani 1 1 d . . . . .
C13 C 0.7176(2) 0.6004(2) 1.09852(19) 0.0467(5) Uani 1 1 d . . . . .
C14 C 0.6617(3) 0.5681(3) 1.2080(2) 0.0627(7) Uani 1 1 d . . . . .
H14 H 0.6444 0.4800 1.2171 0.075 Uiso 1 1 calc R U . . .
C15 C 0.6320(3) 0.6626(3) 1.3016(2) 0.0701(8) Uani 1 1 d . . . . .
H15 H 0.5940 0.6394 1.3736 0.084 Uiso 1 1 calc R U . . .
C16 C 0.6589(3) 0.7933(3) 1.2887(2) 0.0661(7) Uani 1 1 d . . . . .
H16 H 0.6417 0.8588 1.3539 0.079 Uiso 1 1 calc R U . . .
C17 C 0.7104(3) 0.8283(2) 1.1819(2) 0.0552(6) Uani 1 1 d . . . . .
H17 H 0.7256 0.9166 1.1741 0.066 Uiso 1 1 calc R U . . .
C18 C 0.7539(3) 0.4973(2) 1.0014(2) 0.0540(6) Uani 1 1 d . . . . .
C19 C 0.7448(4) 0.2687(3) 0.9330(3) 0.0888(9) Uani 1 1 d . . . . .
H19A H 0.6997 0.2707 0.8467 0.133 Uiso 1 1 calc R U . . .
H19B H 0.6926 0.1832 0.9489 0.133 Uiso 1 1 calc R U . . .
H19C H 0.8625 0.2808 0.9419 0.133 Uiso 1 1 calc R U . . .
N1 N 0.8715(2) 0.74767(17) 0.73369(15) 0.0443(4) Uani 1 1 d . . . . .
N2 N 0.7888(2) 0.76414(16) 0.97223(15) 0.0468(4) Uani 1 1 d . . . . .
H2N H 0.8158 0.7013 0.9224 0.056 Uiso 1 1 calc R U . . .
O1 O 0.7144(2) 0.37521(16) 1.02491(16) 0.0717(5) Uani 1 1 d . . . . .
O2 O 0.8137(2) 0.51556(17) 0.90723(16) 0.0738(5) Uani 1 1 d . . . . .
O3 O 0.7799(2) 0.98089(17) 0.99096(17) 0.0751(5) Uani 1 1 d . . . . .
O4 O 0.59903(18) 0.65746(17) 0.65324(16) 0.0684(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 0.0033 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'
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 119.9(2) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C3 C2 C1 119.0(2) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 121.2(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 117.75(19) . . ?
C6 C5 C7 123.39(17) . . ?
C4 C5 C7 118.84(17) . . ?
C5 C6 C1 121.5(2) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
N1 C7 C5 114.48(15) . . ?
N1 C7 H7A 108.6 . . ?
C5 C7 H7A 108.6 . . ?
N1 C7 H7B 108.6 . . ?
C5 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
O4 C8 N1 119.2(2) . . ?
O4 C8 C9 122.8(2) . . ?
N1 C8 C9 118.0(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C11 116.68(16) . . ?
N1 C10 H10A 108.1 . . ?
C11 C10 H10A 108.1 . . ?
N1 C10 H10B 108.1 . . ?
C11 C10 H10B 108.1 . . ?
H10A C10 H10B 107.3 . . ?
O3 C11 N2 125.39(19) . . ?
O3 C11 C10 119.69(18) . . ?
N2 C11 C10 114.92(18) . . ?
C17 C12 N2 122.41(19) . . ?
C17 C12 C13 119.09(18) . . ?
N2 C12 C13 118.48(19) . . ?
C14 C13 C12 118.6(2) . . ?
C14 C13 C18 120.1(2) . . ?
C12 C13 C18 121.32(17) . . ?
C15 C14 C13 121.4(2) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 119.4(2) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C17 C16 C15 121.0(2) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C12 120.5(2) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
O2 C18 O1 120.8(2) . . ?
O2 C18 C13 126.02(19) . . ?
O1 C18 C13 113.1(2) . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C8 N1 C10 118.25(17) . . ?
C8 N1 C7 123.64(19) . . ?
C10 N1 C7 117.78(18) . . ?
C11 N2 C12 129.41(18) . . ?
C11 N2 H2N 115.3 . . ?
C12 N2 H2N 115.3 . . ?
C18 O1 C19 116.3(2) . . ?
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 1.365(3) . ?
C1 C6 1.379(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.359(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.366(3) . ?
C5 C7 1.511(3) . ?
C6 H6 0.9300 . ?
C7 N1 1.451(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O4 1.215(2) . ?
C8 N1 1.377(3) . ?
C8 C9 1.481(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N1 1.436(3) . ?
C10 C11 1.510(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O3 1.206(2) . ?
C11 N2 1.349(2) . ?
C12 C17 1.382(3) . ?
C12 N2 1.402(2) . ?
C12 C13 1.408(3) . ?
C13 C14 1.397(3) . ?
C13 C18 1.465(3) . ?
C14 C15 1.359(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.378(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.366(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O2 1.217(2) . ?
C18 O1 1.331(3) . ?
C19 O1 1.434(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N2 H2N 0.8600 . ?
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
N2 H2N O2 0.86 1.93 2.638(2) 139.2 .
N2 H2N N1 0.86 2.26 2.725(2) 114.1 .
C7 H7B O3 0.97 2.58 3.489(3) 156.8 2_777
C19 H19B O3 0.96 2.52 3.290(3) 136.9 1_545
C17 H17 O3 0.93 2.27 2.884(3) 122.9 .
C9 H9C O4 0.96 2.65 3.611(3) 174.5 2_666
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 0.4(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C3 C4 C5 C7 178.2(2) . . . . ?
C4 C5 C6 C1 1.2(4) . . . . ?
C7 C5 C6 C1 -177.6(2) . . . . ?
C2 C1 C6 C5 -1.1(4) . . . . ?
C6 C5 C7 N1 -5.0(3) . . . . ?
C4 C5 C7 N1 176.2(2) . . . . ?
N1 C10 C11 O3 176.32(19) . . . . ?
N1 C10 C11 N2 -3.1(3) . . . . ?
C17 C12 C13 C14 1.5(3) . . . . ?
N2 C12 C13 C14 -177.01(18) . . . . ?
C17 C12 C13 C18 -177.50(19) . . . . ?
N2 C12 C13 C18 3.9(3) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?
C18 C13 C14 C15 177.9(2) . . . . ?
C13 C14 C15 C16 -0.5(4) . . . . ?
C14 C15 C16 C17 1.8(4) . . . . ?
C15 C16 C17 C12 -1.4(3) . . . . ?
N2 C12 C17 C16 178.18(18) . . . . ?
C13 C12 C17 C16 -0.3(3) . . . . ?
C14 C13 C18 O2 -174.7(2) . . . . ?
C12 C13 C18 O2 4.3(4) . . . . ?
C14 C13 C18 O1 5.4(3) . . . . ?
C12 C13 C18 O1 -175.56(17) . . . . ?
O4 C8 N1 C10 -3.4(3) . . . . ?
C9 C8 N1 C10 176.21(17) . . . . ?
O4 C8 N1 C7 -176.57(17) . . . . ?
C9 C8 N1 C7 3.1(3) . . . . ?
C11 C10 N1 C8 89.0(2) . . . . ?
C11 C10 N1 C7 -97.5(2) . . . . ?
C5 C7 N1 C8 84.7(2) . . . . ?
C5 C7 N1 C10 -88.5(2) . . . . ?
O3 C11 N2 C12 6.4(4) . . . . ?
C10 C11 N2 C12 -174.23(18) . . . . ?
C17 C12 N2 C11 -7.1(3) . . . . ?
C13 C12 N2 C11 171.36(19) . . . . ?
O2 C18 O1 C19 -0.6(3) . . . . ?
C13 C18 O1 C19 179.34(19) . . . . ?
