#------------------------------------------------------------------------------
#$Date: 2020-04-05 13:13:49 +0300 (Sun, 05 Apr 2020) $
#$Revision: 250200 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/59/7125984.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_7125984
loop_
_publ_author_name
'Carreira-Barral, Israel'
'Mielczarek, Marcin'
'Alonso-Carrillo, Daniel'
'Capurro, Valeria'
'Soto-Cerrato, Vanessa'
'Pérez Tomás, Ricardo'
'Caci, Emanuela'
'García-Valverde, María'
'Quesada, Roberto'
_publ_section_title
;
 Click-tambjamines as efficient and tunable bioactive anion transporters.
;
_journal_issue                   21
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3218
_journal_page_last               3221
_journal_paper_doi               10.1039/d0cc00643b
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C17 H17 Cl N5 O, Cl'
_chemical_formula_sum            'C17 H17 Cl2 N5 O'
_chemical_formula_weight         378.25
_chemical_name_systematic        MM75
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2020-01-23 deposited with the CCDC.	2020-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.478(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7035(14)
_cell_length_b                   20.182(5)
_cell_length_c                   15.891(4)
_cell_measurement_reflns_used    5853
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.61
_cell_measurement_theta_min      2.39
_cell_volume                     1817.5(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1077
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20460
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.291
_diffrn_reflns_theta_min         1.638
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0517
_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)+(0.0855P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1537
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2758
_reflns_number_total             4221
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc00643b2.cif
_cod_data_source_block           MM75
_cod_depositor_comments
'Adding full bibliography for 7125982--7125984.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7125984
_shelx_shelxl_version_number     2016/6
_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   0.896
_shelx_estimated_absorpt_t_max   0.964
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.5986(4) 0.11714(12) 0.36379(13) 0.0620(6) Uani 1 1 d . . . . .
C2 C 0.5272(4) 0.17774(11) 0.38997(14) 0.0612(5) Uani 1 1 d . . . . .
H2 H 0.591754 0.217180 0.369456 0.073 Uiso 1 1 calc R U . . .
C3 C 0.3611(4) 0.18102(10) 0.44632(13) 0.0550(5) Uani 1 1 d . . . . .
H3 H 0.310788 0.222789 0.465218 0.066 Uiso 1 1 calc R U . . .
C4 C 0.2683(3) 0.12352(9) 0.47507(12) 0.0469(4) Uani 1 1 d . . . . .
C5 C 0.3377(4) 0.06266(10) 0.44684(13) 0.0596(5) Uani 1 1 d . . . . .
H5 H 0.269642 0.023131 0.465608 0.072 Uiso 1 1 calc R U . . .
C6 C 0.5063(4) 0.05957(12) 0.39129(14) 0.0675(6) Uani 1 1 d . . . . .
H6 H 0.557856 0.017952 0.372347 0.081 Uiso 1 1 calc R U . . .
C7 C -0.0440(3) 0.17602(9) 0.55147(12) 0.0481(4) Uani 1 1 d . . . . .
C8 C -0.1687(3) 0.15235(9) 0.61317(12) 0.0477(4) Uani 1 1 d . . . . .
C9 C -0.3528(3) 0.18450(9) 0.65357(11) 0.0477(4) Uani 1 1 d . . . . .
C10 C -0.4914(3) 0.16119(9) 0.71361(12) 0.0534(5) Uani 1 1 d . . . . .
H10 H -0.480279 0.119061 0.740415 0.064 Uiso 1 1 calc R U . . .
C11 C -0.6492(3) 0.21126(10) 0.72685(13) 0.0533(5) Uani 1 1 d . . . . .
C12 C -0.8434(5) 0.15720(13) 0.82979(16) 0.0802(7) Uani 1 1 d . . . . .
H12A H -0.874370 0.117936 0.793963 0.120 Uiso 1 1 calc R U . . .
H12B H -0.974735 0.164013 0.863632 0.120 Uiso 1 1 calc R U . . .
H12C H -0.697094 0.150726 0.867558 0.120 Uiso 1 1 calc R U . . .
C13 C -0.6038(3) 0.26538(9) 0.67467(12) 0.0498(5) Uani 1 1 d . . . . .
C14 C -0.7135(4) 0.32648(10) 0.66664(14) 0.0576(5) Uani 1 1 d . . . . .
H14 H -0.840100 0.334321 0.699429 0.069 Uiso 1 1 calc R U . . .
C15 C -0.7772(5) 0.43755(12) 0.60654(19) 0.0893(8) Uani 1 1 d . . . . .
H15 H -0.916791 0.437610 0.562411 0.107 Uiso 1 1 calc R U . . .
C16 C -0.6491(6) 0.49579(15) 0.6116(3) 0.1354(15) Uani 1 1 d . . . . .
H16A H -0.701447 0.531728 0.571382 0.162 Uiso 1 1 calc R U . . .
H16B H -0.476283 0.492766 0.626816 0.162 Uiso 1 1 calc R U . . .
C17 C -0.8001(8) 0.47895(16) 0.6760(3) 0.1374(15) Uani 1 1 d . . . . .
H17A H -0.723954 0.464883 0.732194 0.165 Uiso 1 1 calc R U . . .
H17B H -0.949320 0.503880 0.676709 0.165 Uiso 1 1 calc R U . . .
N1 N 0.0988(3) 0.12606(7) 0.53445(10) 0.0472(4) Uani 1 1 d . . . . .
N2 N 0.0655(3) 0.07312(8) 0.58432(11) 0.0601(5) Uani 1 1 d . . . . .
N3 N -0.0978(3) 0.08908(8) 0.63196(11) 0.0593(5) Uani 1 1 d . . . . .
N4 N -0.4187(3) 0.24639(7) 0.63144(10) 0.0487(4) Uani 1 1 d . . . . .
N5 N -0.6563(3) 0.37429(8) 0.61733(13) 0.0640(5) Uani 1 1 d . . . . .
O1 O -0.8200(3) 0.21393(8) 0.77760(10) 0.0678(4) Uani 1 1 d . . . . .
Cl1 Cl 0.81069(11) 0.11232(4) 0.29371(5) 0.0971(3) Uani 1 1 d . . . . .
Cl2 Cl 0.74044(10) 0.33953(3) 0.49728(4) 0.0709(2) Uani 1 1 d . . . . .
H7 H -0.045(3) 0.2146(10) 0.5216(13) 0.056(6) Uiso 1 1 d . . . . .
H4N H -0.358(3) 0.2688(10) 0.5944(13) 0.058(6) Uiso 1 1 d . . . . .
H5N H -0.536(5) 0.3676(13) 0.5750(17) 0.094(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'
Cl Cl 0.1484 0.1585 '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
C6 C1 C2 121.6(2) . . ?
C6 C1 Cl1 118.57(18) . . ?
C2 C1 Cl1 119.84(18) . . ?
C1 C2 C3 119.4(2) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 119.63(19) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.51(19) . . ?
C3 C4 N1 120.30(16) . . ?
C5 C4 N1 119.19(16) . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C1 C6 C5 119.2(2) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
N1 C7 C8 105.05(17) . . ?
N1 C7 H7 120.3(12) . . ?
C8 C7 H7 134.5(12) . . ?
C7 C8 N3 108.68(16) . . ?
C7 C8 C9 128.86(17) . . ?
N3 C8 C9 122.44(17) . . ?
N4 C9 C10 109.35(17) . . ?
N4 C9 C8 119.91(17) . . ?
C10 C9 C8 130.70(18) . . ?
C11 C10 C9 106.71(17) . . ?
C11 C10 H10 126.6 . . ?
C9 C10 H10 126.6 . . ?
O1 C11 C10 130.73(19) . . ?
O1 C11 C13 121.22(18) . . ?
C10 C11 C13 108.05(17) . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C13 C14 124.53(18) . . ?
N4 C13 C11 106.20(16) . . ?
C14 C13 C11 129.26(19) . . ?
N5 C14 C13 124.94(19) . . ?
N5 C14 H14 117.5 . . ?
C13 C14 H14 117.5 . . ?
C16 C15 C17 62.8(2) . . ?
C16 C15 N5 120.0(3) . . ?
C17 C15 N5 121.1(3) . . ?
C16 C15 H15 114.4 . . ?
C17 C15 H15 114.4 . . ?
N5 C15 H15 114.4 . . ?
C15 C16 C17 59.3(2) . . ?
C15 C16 H16A 117.8 . . ?
C17 C16 H16A 117.8 . . ?
C15 C16 H16B 117.8 . . ?
C17 C16 H16B 117.8 . . ?
H16A C16 H16B 115.0 . . ?
C15 C17 C16 57.9(2) . . ?
C15 C17 H17A 118.0 . . ?
C16 C17 H17A 118.0 . . ?
C15 C17 H17B 118.0 . . ?
C16 C17 H17B 118.0 . . ?
H17A C17 H17B 115.1 . . ?
C7 N1 N2 110.22(16) . . ?
C7 N1 C4 129.21(15) . . ?
N2 N1 C4 120.56(14) . . ?
N3 N2 N1 107.50(15) . . ?
N2 N3 C8 108.54(16) . . ?
C9 N4 C13 109.69(16) . . ?
C9 N4 H4N 123.7(14) . . ?
C13 N4 H4N 126.5(14) . . ?
C14 N5 C15 124.9(2) . . ?
C14 N5 H5N 121.9(15) . . ?
C15 N5 H5N 112.5(15) . . ?
C11 O1 C12 116.17(17) . . ?
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 C6 1.367(3) . ?
C1 C2 1.368(3) . ?
C1 Cl1 1.737(2) . ?
C2 C3 1.377(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(3) . ?
C4 N1 1.426(2) . ?
C5 C6 1.378(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.343(2) . ?
C7 C8 1.361(3) . ?
C7 H7 0.91(2) . ?
C8 N3 1.362(2) . ?
C8 C9 1.445(3) . ?
C9 N4 1.340(2) . ?
C9 C10 1.388(3) . ?
C10 C11 1.385(3) . ?
C10 H10 0.9500 . ?
C11 O1 1.334(2) . ?
C11 C13 1.413(3) . ?
C12 O1 1.429(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N4 1.377(2) . ?
C13 C14 1.382(3) . ?
C14 N5 1.307(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(4) . ?
C15 C17 1.401(4) . ?
C15 N5 1.452(3) . ?
C15 H15 1.0000 . ?
C16 C17 1.450(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
N1 N2 1.356(2) . ?
N2 N3 1.305(2) . ?
N4 H4N 0.85(2) . ?
N5 H5N 1.02(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
C12 H12B Cl2 0.98 2.82 3.761(3) 162.2 4_366
C14 H14 Cl1 0.95 2.84 3.769(2) 167.2 4_366
C15 H15 Cl2 1.00 2.89 3.663(3) 134.7 1_355
C16 H16A Cl2 0.99 2.82 3.756(3) 158.5 3_566
C7 H7 Cl2 0.91(2) 2.81(2) 3.592(2) 144.6(15) 1_455
N4 H4N Cl2 0.85(2) 2.22(2) 3.0561(18) 169.0(18) 1_455
N5 H5N Cl2 1.02(3) 2.19(3) 3.198(2) 171(2) 1_455
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 1.0(3) . . . . ?
Cl1 C1 C2 C3 -179.23(15) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C2 C3 C4 N1 179.02(17) . . . . ?
C3 C4 C5 C6 1.9(3) . . . . ?
N1 C4 C5 C6 -178.17(18) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
Cl1 C1 C6 C5 -179.93(16) . . . . ?
C4 C5 C6 C1 -1.3(3) . . . . ?
N1 C7 C8 N3 0.2(2) . . . . ?
N1 C7 C8 C9 -178.00(17) . . . . ?
C7 C8 C9 N4 -0.7(3) . . . . ?
N3 C8 C9 N4 -178.71(17) . . . . ?
C7 C8 C9 C10 176.6(2) . . . . ?
N3 C8 C9 C10 -1.4(3) . . . . ?
N4 C9 C10 C11 0.9(2) . . . . ?
C8 C9 C10 C11 -176.67(18) . . . . ?
C9 C10 C11 O1 179.62(18) . . . . ?
C9 C10 C11 C13 -0.4(2) . . . . ?
O1 C11 C13 N4 179.80(16) . . . . ?
C10 C11 C13 N4 -0.2(2) . . . . ?
O1 C11 C13 C14 0.7(3) . . . . ?
C10 C11 C13 C14 -179.26(19) . . . . ?
N4 C13 C14 N5 -0.2(3) . . . . ?
C11 C13 C14 N5 178.8(2) . . . . ?
N5 C15 C16 C17 -111.9(3) . . . . ?
N5 C15 C17 C16 110.3(3) . . . . ?
C8 C7 N1 N2 -0.4(2) . . . . ?
C8 C7 N1 C4 -179.84(17) . . . . ?
C3 C4 N1 C7 21.8(3) . . . . ?
C5 C4 N1 C7 -158.14(19) . . . . ?
C3 C4 N1 N2 -157.56(17) . . . . ?
C5 C4 N1 N2 22.5(3) . . . . ?
C7 N1 N2 N3 0.5(2) . . . . ?
C4 N1 N2 N3 179.95(16) . . . . ?
N1 N2 N3 C8 -0.3(2) . . . . ?
C7 C8 N3 N2 0.1(2) . . . . ?
C9 C8 N3 N2 178.42(17) . . . . ?
C10 C9 N4 C13 -1.0(2) . . . . ?
C8 C9 N4 C13 176.85(16) . . . . ?
C14 C13 N4 C9 179.85(17) . . . . ?
C11 C13 N4 C9 0.7(2) . . . . ?
C13 C14 N5 C15 177.6(2) . . . . ?
C16 C15 N5 C14 131.8(3) . . . . ?
C17 C15 N5 C14 57.3(4) . . . . ?
C10 C11 O1 C12 2.3(3) . . . . ?
C13 C11 O1 C12 -177.68(19) . . . . ?
