#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:13:27 +0300 (Fri, 05 May 2023) $
#$Revision: 283441 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/92/7159252.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_7159252
loop_
_publ_author_name
'Roy, Naveen J.'
'Pujari, Parappa L.'
'Talukdar, Pinaki'
_publ_section_title
;
 Bimodal structural tuning of pyrrole-2-carboxamide-based transmembrane
 ion transport systems.
;
_journal_issue                   16
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3323
_journal_page_last               3329
_journal_paper_doi               10.1039/d3ob00269a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C15 H15 Br N2 O2'
_chemical_formula_weight         335.20
_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-2018/3
_audit_update_record
;
2023-02-15 deposited with the CCDC.	2023-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                67.863(17)
_cell_angle_beta                 80.098(17)
_cell_angle_gamma                77.161(16)
_cell_formula_units_Z            4
_cell_length_a                   7.588(4)
_cell_length_b                   13.617(8)
_cell_length_c                   14.984(9)
_cell_measurement_reflns_used    2902
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.67
_cell_measurement_theta_min      2.82
_cell_volume                     1391.6(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0882
_diffrn_reflns_av_unetI/netI     0.1263
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22357
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.574
_diffrn_reflns_theta_min         1.474
_diffrn_source                   'ceramic sealed tube'
_exptl_absorpt_coefficient_mu    2.957
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.5360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate'
_exptl_crystal_size_max          0.559
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.101
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.804
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       0.0007(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         7792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.963
_refine_ls_R_factor_all          0.1174
_refine_ls_R_factor_gt           0.0509
_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)+(0.0338P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1196
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4415
_reflns_number_total             7792
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00269a2.cif
_cod_data_source_block           try1_ax
_cod_depositor_comments
'Adding full bibliography for 7159252--7159253.cif.'
_cod_database_code               7159252
_shelx_shelxl_version_number     2018/3
_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.
;
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
Br1 Br 1.24447(5) 0.44607(3) 0.05011(3) 0.03068(13) Uani 1 1 d . . . . .
O1 O 0.5027(3) 0.1327(2) 0.81853(19) 0.0277(7) Uani 1 1 d . . . . .
N1 N 0.5964(4) 0.4751(2) 0.6460(2) 0.0173(7) Uani 1 1 d . . . . .
H1 H 0.609970 0.541057 0.628031 0.021 Uiso 1 1 calc R U . . .
C1 C 0.4470(5) 0.4731(3) 0.8067(3) 0.0228(9) Uani 1 1 d . . . . .
H1A H 0.483064 0.542400 0.784020 0.034 Uiso 1 1 calc R U . . .
H1B H 0.498346 0.428847 0.866320 0.034 Uiso 1 1 calc R U . . .
H1C H 0.316982 0.481640 0.817427 0.034 Uiso 1 1 calc R U . . .
O2 O 0.7845(3) 0.55104(18) 0.46518(18) 0.0202(6) Uani 1 1 d . . . . .
Br2 Br 0.17882(5) 0.80333(3) 1.04603(3) 0.02654(12) Uani 1 1 d . . . . .
N2 N 0.8217(4) 0.3878(2) 0.4467(2) 0.0209(7) Uani 1 1 d . . . . .
H2 H 0.796664 0.324100 0.476087 0.025 Uiso 1 1 calc R U . . .
C2 C 0.5137(4) 0.4207(3) 0.7325(3) 0.0173(8) Uani 1 1 d . . . . .
N3 N 0.7903(4) 0.7738(2) 0.4425(2) 0.0168(7) Uani 1 1 d . . . . .
H3 H 0.769846 0.709501 0.458114 0.020 Uiso 1 1 calc R U . . .
O3 O 1.0318(3) 1.08011(19) 0.31302(19) 0.0221(6) Uani 1 1 d . . . . .
C3 C 0.5185(4) 0.3166(3) 0.7341(3) 0.0168(8) Uani 1 1 d . . . . .
O4 O 0.5634(3) 0.71048(19) 0.61372(18) 0.0204(6) Uani 1 1 d . . . . .
N4 N 0.6243(4) 0.8429(2) 0.6580(2) 0.0178(7) Uani 1 1 d . . . . .
H4 H 0.691492 0.891522 0.640207 0.021 Uiso 1 1 calc R U . . .
C4 C 0.6081(4) 0.3108(3) 0.6430(3) 0.0160(8) Uani 1 1 d . . . . .
C5 C 0.6563(4) 0.4113(3) 0.5902(3) 0.0168(8) Uani 1 1 d . . . . .
C6 C 0.4522(5) 0.2262(3) 0.8158(3) 0.0185(8) Uani 1 1 d . . . . .
C7 C 0.3196(5) 0.2493(3) 0.8963(3) 0.0229(9) Uani 1 1 d . . . . .
H7A H 0.381970 0.268706 0.936037 0.034 Uiso 1 1 calc R U . . .
H7B H 0.268223 0.186175 0.934970 0.034 Uiso 1 1 calc R U . . .
H7C H 0.224383 0.307478 0.868765 0.034 Uiso 1 1 calc R U . . .
C8 C 0.6334(5) 0.2161(3) 0.6099(3) 0.0210(8) Uani 1 1 d . . . . .
H8A H 0.596653 0.240651 0.545745 0.032 Uiso 1 1 calc R U . . .
H8B H 0.560634 0.164837 0.653293 0.032 Uiso 1 1 calc R U . . .
H8C H 0.758950 0.182822 0.609559 0.032 Uiso 1 1 calc R U . . .
C9 C 0.7582(4) 0.4574(3) 0.4959(3) 0.0169(8) Uani 1 1 d . . . . .
C10 C 0.9221(4) 0.4044(3) 0.3551(3) 0.0167(8) Uani 1 1 d . . . . .
C12 C 1.0921(5) 0.5093(3) 0.2129(3) 0.0224(9) Uani 1 1 d . . . . .
H12 H 1.141397 0.571179 0.177954 0.027 Uiso 1 1 calc R U . . .
C11 C 0.9980(5) 0.4973(3) 0.3040(3) 0.0234(9) Uani 1 1 d . . . . .
H11 H 0.985780 0.550545 0.330450 0.028 Uiso 1 1 calc R U . . .
C15 C 0.9465(5) 0.3246(3) 0.3154(3) 0.0202(8) Uani 1 1 d . . . . .
H15 H 0.897521 0.262521 0.349904 0.024 Uiso 1 1 calc R U . . .
C14 C 1.0422(4) 0.3353(3) 0.2257(3) 0.0187(8) Uani 1 1 d . . . . .
H14 H 1.059183 0.280835 0.200317 0.022 Uiso 1 1 calc R U . . .
C13 C 1.1123(4) 0.4292(3) 0.1744(3) 0.0201(9) Uani 1 1 d . . . . .
C16 C 0.9334(5) 0.7807(3) 0.2795(3) 0.0225(9) Uani 1 1 d . . . . .
H16A H 0.890564 0.831168 0.219489 0.034 Uiso 1 1 calc R U . . .
H16B H 0.884312 0.715979 0.297289 0.034 Uiso 1 1 calc R U . . .
H16C H 1.063587 0.764201 0.272037 0.034 Uiso 1 1 calc R U . . .
C17 C 0.8732(4) 0.8291(3) 0.3574(3) 0.0155(8) Uani 1 1 d . . . . .
C18 C 0.8853(4) 0.9294(3) 0.3601(2) 0.0139(7) Uani 1 1 d . . . . .
C19 C 0.7978(4) 0.9341(3) 0.4519(3) 0.0139(7) Uani 1 1 d . . . . .
C20 C 0.7423(4) 0.8348(3) 0.5019(3) 0.0157(8) Uani 1 1 d . . . . .
C21 C 0.9879(4) 1.0114(3) 0.2900(3) 0.0175(8) Uani 1 1 d . . . . .
C22 C 1.0460(5) 1.0085(3) 0.1895(3) 0.0227(9) Uani 1 1 d . . . . .
H22A H 0.946435 0.997168 0.164793 0.034 Uiso 1 1 calc R U . . .
H22B H 1.146443 0.950826 0.191736 0.034 Uiso 1 1 calc R U . . .
H22C H 1.082014 1.075599 0.147851 0.034 Uiso 1 1 calc R U . . .
C23 C 0.7552(4) 1.0320(3) 0.4818(3) 0.0182(8) Uani 1 1 d . . . . .
H23A H 0.746596 1.096069 0.425109 0.027 Uiso 1 1 calc R U . . .
H23B H 0.850091 1.030540 0.517402 0.027 Uiso 1 1 calc R U . . .
H23C H 0.641805 1.031565 0.521785 0.027 Uiso 1 1 calc R U . . .
C24 C 0.6363(4) 0.7899(3) 0.5958(3) 0.0148(8) Uani 1 1 d . . . . .
C25 C 0.5177(4) 0.8301(3) 0.7480(2) 0.0146(8) Uani 1 1 d . . . . .
C26 C 0.3926(4) 0.7585(3) 0.7853(3) 0.0178(8) Uani 1 1 d . . . . .
H26 H 0.375442 0.717527 0.750967 0.021 Uiso 1 1 calc R U . . .
C27 C 0.2945(5) 0.7505(3) 0.8753(3) 0.0201(8) Uani 1 1 d . . . . .
H27 H 0.213740 0.702174 0.902068 0.024 Uiso 1 1 calc R U . . .
C28 C 0.3174(5) 0.8139(3) 0.9244(3) 0.0190(8) Uani 1 1 d . . . . .
C29 C 0.4360(5) 0.8872(3) 0.8862(3) 0.0214(9) Uani 1 1 d . . . . .
H29 H 0.448768 0.930469 0.919318 0.026 Uiso 1 1 calc R U . . .
C30 C 0.5350(5) 0.8948(3) 0.7976(3) 0.0195(8) Uani 1 1 d . . . . .
H30 H 0.614293 0.943967 0.771113 0.023 Uiso 1 1 calc R U . . .
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'
Br Br -0.2901 2.4595 '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 N1 C5 111.4(3) . . ?
C2 N1 H1 124.3 . . ?
C5 N1 H1 124.3 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C9 N2 C10 130.1(3) . . ?
C9 N2 H2 114.9 . . ?
C10 N2 H2 114.9 . . ?
N1 C2 C3 107.0(3) . . ?
N1 C2 C1 120.2(3) . . ?
C3 C2 C1 132.6(3) . . ?
C17 N3 C20 110.6(3) . . ?
C17 N3 H3 124.7 . . ?
C20 N3 H3 124.7 . . ?
C2 C3 C4 107.7(3) . . ?
C2 C3 C6 126.8(3) . . ?
C4 C3 C6 125.5(3) . . ?
C24 N4 C25 129.8(3) . . ?
C24 N4 H4 115.1 . . ?
C25 N4 H4 115.1 . . ?
C5 C4 C3 106.3(3) . . ?
C5 C4 C8 127.3(3) . . ?
C3 C4 C8 126.2(3) . . ?
N1 C5 C4 107.6(3) . . ?
N1 C5 C9 117.8(3) . . ?
C4 C5 C9 134.5(3) . . ?
O1 C6 C3 120.7(3) . . ?
O1 C6 C7 119.7(3) . . ?
C3 C6 C7 119.6(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 N2 123.5(3) . . ?
O2 C9 C5 121.8(3) . . ?
N2 C9 C5 114.7(3) . . ?
C15 C10 C11 119.4(4) . . ?
C15 C10 N2 118.2(3) . . ?
C11 C10 N2 122.4(3) . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C11 C10 119.3(4) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C14 C15 C10 121.6(3) . . ?
C14 C15 H15 119.2 . . ?
C10 C15 H15 119.2 . . ?
C15 C14 C13 118.5(4) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C12 C13 C14 121.1(3) . . ?
C12 C13 Br1 119.6(3) . . ?
C14 C13 Br1 119.3(3) . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 C18 107.9(3) . . ?
N3 C17 C16 120.5(3) . . ?
C18 C17 C16 131.6(3) . . ?
C17 C18 C19 107.5(3) . . ?
C17 C18 C21 128.1(3) . . ?
C19 C18 C21 123.9(3) . . ?
C20 C19 C18 105.9(3) . . ?
C20 C19 C23 127.4(3) . . ?
C18 C19 C23 126.3(3) . . ?
N3 C20 C19 108.0(3) . . ?
N3 C20 C24 118.0(3) . . ?
C19 C20 C24 133.7(3) . . ?
O3 C21 C18 121.4(3) . . ?
O3 C21 C22 119.5(3) . . ?
C18 C21 C22 119.1(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O4 C24 N4 124.1(3) . . ?
O4 C24 C20 121.0(3) . . ?
N4 C24 C20 114.9(3) . . ?
C30 C25 C26 120.0(3) . . ?
C30 C25 N4 117.4(3) . . ?
C26 C25 N4 122.5(3) . . ?
C27 C26 C25 118.5(4) . . ?
C27 C26 H26 120.7 . . ?
C25 C26 H26 120.7 . . ?
C28 C27 C26 120.3(3) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C27 C28 C29 121.3(3) . . ?
C27 C28 Br2 119.5(3) . . ?
C29 C28 Br2 119.1(3) . . ?
C30 C29 C28 118.7(4) . . ?
C30 C29 H29 120.7 . . ?
C28 C29 H29 120.7 . . ?
C25 C30 C29 121.1(3) . . ?
C25 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
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
Br1 C13 1.915(4) . ?
O1 C6 1.233(4) . ?
N1 C2 1.352(4) . ?
N1 C5 1.379(4) . ?
N1 H1 0.8600 . ?
C1 C2 1.499(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
O2 C9 1.232(4) . ?
Br2 C28 1.913(4) . ?
N2 C9 1.369(4) . ?
N2 C10 1.414(4) . ?
N2 H2 0.8600 . ?
C2 C3 1.402(5) . ?
N3 C17 1.342(4) . ?
N3 C20 1.388(4) . ?
N3 H3 0.8600 . ?
O3 C21 1.235(4) . ?
C3 C4 1.438(5) . ?
C3 C6 1.481(5) . ?
O4 C24 1.243(4) . ?
N4 C24 1.359(5) . ?
N4 C25 1.418(4) . ?
N4 H4 0.8600 . ?
C4 C5 1.392(5) . ?
C4 C8 1.511(5) . ?
C5 C9 1.469(5) . ?
C6 C7 1.514(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C10 C15 1.388(5) . ?
C10 C11 1.400(5) . ?
C12 C13 1.382(5) . ?
C12 C11 1.396(5) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C15 C14 1.386(5) . ?
C15 H15 0.9300 . ?
C14 C13 1.389(5) . ?
C14 H14 0.9300 . ?
C16 C17 1.506(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.405(5) . ?
C18 C19 1.439(5) . ?
C18 C21 1.476(5) . ?
C19 C20 1.396(5) . ?
C19 C23 1.514(5) . ?
C20 C24 1.476(5) . ?
C21 C22 1.509(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C25 C30 1.388(5) . ?
C25 C26 1.408(5) . ?
C26 C27 1.402(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.381(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.388(5) . ?
C29 C30 1.388(5) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
