#------------------------------------------------------------------------------
#$Date: 2020-10-06 09:16:24 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257259 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/70/7127056.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_7127056
loop_
_publ_author_name
'Picci, Giacomo'
'Kubicki, Maciej'
'Garau, Alessandra'
'Lippolis, Vito'
'Mocci, Rita'
'Porcheddu, Andrea'
'Quesada, Roberto'
'Ricci, Pier Carlo'
'Scorciapino, M. Andrea'
'Caltagirone, Claudia'
_publ_section_title
;
 Simple squaramide receptors for highly efficient anion binding in aqueous
 media and transmembrane transport.
;
_journal_issue                   75
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11066
_journal_page_last               11069
_journal_paper_doi               10.1039/d0cc04090h
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C22 H14 N4 O2, H2 O'
_chemical_formula_sum            'C22 H16 N4 O3'
_chemical_formula_weight         384.39
_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   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2019-07-30 deposited with the CCDC.	2020-08-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.3166(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.60987(13)
_cell_length_b                   10.80108(11)
_cell_length_c                   13.03058(13)
_cell_measurement_reflns_used    8549
_cell_measurement_temperature    130(1)
_cell_measurement_theta_max      76.1010
_cell_measurement_theta_min      4.0790
_cell_volume                     1733.92(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2013)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      130(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0126
_diffrn_reflns_av_unetI/netI     0.0112
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10165
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         76.295
_diffrn_reflns_theta_min         4.430
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.829
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         3586
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0340
_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)+(0.0525P)²+0.5520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.0982
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3371
_reflns_number_total             3586
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc04090h2.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 7127055--7127057.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7127056
_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.
;
_shelxl_version_number           2013-4
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_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 0.78455(9) 0.68541(11) 0.55355(9) 0.0260(2) Uani 1 1 d . . . . .
O1 O 0.80184(7) 0.71200(9) 0.64668(7) 0.0332(2) Uani 1 1 d . . . . .
C2 C 0.85647(9) 0.66812(12) 0.47636(10) 0.0291(3) Uani 1 1 d . . . . .
O2 O 0.95317(7) 0.68199(11) 0.48029(8) 0.0427(3) Uani 1 1 d . . . . .
C3 C 0.75870(9) 0.63220(11) 0.39741(9) 0.0243(2) Uani 1 1 d . . . . .
N3 N 0.73433(8) 0.59393(10) 0.29743(7) 0.0259(2) Uani 1 1 d . . . . .
H3 H 0.6632(14) 0.5991(15) 0.2621(12) 0.037(4) Uiso 1 1 d . . . . .
C30 C 0.80674(9) 0.54410(11) 0.23965(9) 0.0251(2) Uani 1 1 d . . . . .
C31 C 0.90939(9) 0.50361(12) 0.28505(9) 0.0279(3) Uani 1 1 d . . . . .
H31 H 0.9348(13) 0.5067(15) 0.3624(12) 0.036(4) Uiso 1 1 d . . . . .
C32 C 0.97796(10) 0.45597(12) 0.22201(10) 0.0305(3) Uani 1 1 d . . . . .
H32 H 1.0515(13) 0.4281(15) 0.2571(12) 0.038(4) Uiso 1 1 d . . . . .
C33 C 0.94400(10) 0.44727(12) 0.11565(10) 0.0301(3) Uani 1 1 d . . . . .
H33 H 0.9927(13) 0.4126(15) 0.0705(12) 0.039(4) Uiso 1 1 d . . . . .
C34 C 0.83791(9) 0.48598(11) 0.06673(9) 0.0268(3) Uani 1 1 d . . . . .
C35 C 0.79692(10) 0.47934(12) -0.04300(10) 0.0318(3) Uani 1 1 d . . . . .
H35 H 0.8454(14) 0.4432(16) -0.0893(13) 0.044(4) Uiso 1 1 d . . . . .
C36 C 0.69343(10) 0.51682(13) -0.08436(10) 0.0330(3) Uani 1 1 d . . . . .
H36 H 0.6623(13) 0.5130(16) -0.1613(13) 0.042(4) Uiso 1 1 d . . . . .
C37 C 0.62923(10) 0.56048(13) -0.01582(9) 0.0308(3) Uani 1 1 d . . . . .
H37 H 0.5537(12) 0.5874(14) -0.0434(11) 0.029(4) Uiso 1 1 d . . . . .
N38 N 0.66351(8) 0.56968(10) 0.08687(8) 0.0274(2) Uani 1 1 d . . . . .
C39 C 0.76742(9) 0.53342(11) 0.12883(9) 0.0249(2) Uani 1 1 d . . . . .
C4 C 0.69045(9) 0.65493(10) 0.46824(9) 0.0234(2) Uani 1 1 d . . . . .
N4 N 0.58222(7) 0.64651(9) 0.45314(7) 0.0232(2) Uani 1 1 d . . . . .
H4 H 0.5438(13) 0.6350(14) 0.3860(12) 0.034(4) Uiso 1 1 d . . . . .
C40 C 0.51698(9) 0.65932(10) 0.52751(9) 0.0233(2) Uani 1 1 d . . . . .
C41 C 0.55622(10) 0.67199(12) 0.63377(9) 0.0280(3) Uani 1 1 d . . . . .
H41 H 0.6324(13) 0.6743(15) 0.6617(12) 0.037(4) Uiso 1 1 d . . . . .
C42 C 0.48348(10) 0.68136(12) 0.70219(9) 0.0301(3) Uani 1 1 d . . . . .
H42 H 0.5113(13) 0.6913(15) 0.7765(12) 0.036(4) Uiso 1 1 d . . . . .
C43 C 0.37376(10) 0.67625(11) 0.66586(9) 0.0277(3) Uani 1 1 d . . . . .
H43 H 0.3251(13) 0.6828(15) 0.7144(12) 0.035(4) Uiso 1 1 d . . . . .
C44 C 0.33090(9) 0.66232(10) 0.55675(9) 0.0240(2) Uani 1 1 d . . . . .
C45 C 0.21833(9) 0.65406(11) 0.51293(10) 0.0270(3) Uani 1 1 d . . . . .
H45 H 0.1668(12) 0.6597(14) 0.5594(11) 0.030(4) Uiso 1 1 d . . . . .
C46 C 0.18380(9) 0.63915(12) 0.40690(10) 0.0290(3) Uani 1 1 d . . . . .
H46 H 0.1054(13) 0.6334(14) 0.3736(12) 0.036(4) Uiso 1 1 d . . . . .
C47 C 0.26150(9) 0.63395(12) 0.34398(9) 0.0285(3) Uani 1 1 d . . . . .
H47 H 0.2381(13) 0.6270(15) 0.2673(13) 0.037(4) Uiso 1 1 d . . . . .
N48 N 0.36741(8) 0.64139(10) 0.38063(8) 0.0261(2) Uani 1 1 d . . . . .
C49 C 0.40238(9) 0.65481(10) 0.48654(9) 0.0225(2) Uani 1 1 d . . . . .
O1W O 0.50903(8) 0.65164(11) 0.21347(7) 0.0381(2) Uani 1 1 d . . . . .
H1W2 H 0.4483(17) 0.6924(19) 0.2094(15) 0.062(6) Uiso 1 1 d . . . . .
H1W1 H 0.5343(19) 0.656(2) 0.1530(19) 0.078(7) 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 0.0181 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C4 138.05(11) . . ?
O1 C1 C2 133.59(10) . . ?
C4 C1 C2 88.35(9) . . ?
O2 C2 C3 137.69(12) . . ?
O2 C2 C1 134.25(11) . . ?
C3 C2 C1 88.03(9) . . ?
N3 C3 C4 130.15(10) . . ?
N3 C3 C2 137.92(11) . . ?
C4 C3 C2 91.93(9) . . ?
C3 N3 C30 126.72(10) . . ?
C3 N3 H3 117.8(10) . . ?
C30 N3 H3 115.5(10) . . ?
C31 C30 N3 123.35(10) . . ?
C31 C30 C39 120.09(11) . . ?
N3 C30 C39 116.53(10) . . ?
C30 C31 C32 120.21(11) . . ?
C30 C31 H31 119.9(9) . . ?
C32 C31 H31 119.9(9) . . ?
C33 C32 C31 121.22(11) . . ?
C33 C32 H32 120.6(9) . . ?
C31 C32 H32 118.2(9) . . ?
C32 C33 C34 119.91(11) . . ?
C32 C33 H33 121.3(9) . . ?
C34 C33 H33 118.8(9) . . ?
C35 C34 C33 123.11(11) . . ?
C35 C34 C39 117.14(11) . . ?
C33 C34 C39 119.75(11) . . ?
C36 C35 C34 119.82(11) . . ?
C36 C35 H35 121.5(9) . . ?
C34 C35 H35 118.7(9) . . ?
C35 C36 C37 118.69(11) . . ?
C35 C36 H36 121.6(9) . . ?
C37 C36 H36 119.7(9) . . ?
N38 C37 C36 124.06(11) . . ?
N38 C37 H37 115.4(8) . . ?
C36 C37 H37 120.6(8) . . ?
C37 N38 C39 117.61(10) . . ?
N38 C39 C34 122.66(11) . . ?
N38 C39 C30 118.58(10) . . ?
C34 C39 C30 118.76(10) . . ?
N4 C4 C3 129.52(10) . . ?
N4 C4 C1 138.94(11) . . ?
C3 C4 C1 91.53(9) . . ?
C4 N4 C40 128.30(10) . . ?
C4 N4 H4 117.7(10) . . ?
C40 N4 H4 113.9(10) . . ?
C41 C40 N4 124.52(10) . . ?
C41 C40 C49 119.82(10) . . ?
N4 C40 C49 115.63(10) . . ?
C40 C41 C42 120.02(11) . . ?
C40 C41 H41 120.3(9) . . ?
C42 C41 H41 119.7(9) . . ?
C43 C42 C41 121.67(11) . . ?
C43 C42 H42 118.6(9) . . ?
C41 C42 H42 119.8(9) . . ?
C42 C43 C44 119.59(11) . . ?
C42 C43 H43 120.3(9) . . ?
C44 C43 H43 120.1(9) . . ?
C45 C44 C49 117.21(10) . . ?
C45 C44 C43 123.13(11) . . ?
C49 C44 C43 119.66(10) . . ?
C46 C45 C44 119.41(11) . . ?
C46 C45 H45 121.4(9) . . ?
C44 C45 H45 119.2(9) . . ?
C45 C46 C47 118.86(11) . . ?
C45 C46 H46 121.4(9) . . ?
C47 C46 H46 119.7(9) . . ?
N48 C47 C46 124.26(11) . . ?
N48 C47 H47 115.7(9) . . ?
C46 C47 H47 120.0(9) . . ?
C47 N48 C49 117.13(10) . . ?
N48 C49 C44 123.12(10) . . ?
N48 C49 C40 117.65(10) . . ?
C44 C49 C40 119.22(10) . . ?
H1W2 O1W H1W1 112.4(19) . . ?
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 O1 1.2205(14) . ?
C1 C4 1.4797(15) . ?
C1 C2 1.5027(16) . ?
C2 O2 1.2187(15) . ?
C2 C3 1.4790(15) . ?
C3 N3 1.3386(15) . ?
C3 C4 1.4113(15) . ?
N3 C30 1.4083(14) . ?
N3 H3 0.918(16) . ?
C30 C31 1.3748(16) . ?
C30 C39 1.4280(16) . ?
C31 C32 1.4107(17) . ?
C31 H31 0.991(16) . ?
C32 C33 1.3637(18) . ?
C32 H32 0.990(17) . ?
C33 C34 1.4166(17) . ?
C33 H33 1.009(16) . ?
C34 C35 1.4147(17) . ?
C34 C39 1.4193(16) . ?
C35 C36 1.3628(18) . ?
C35 H35 1.023(17) . ?
C36 C37 1.4085(18) . ?
C36 H36 0.997(16) . ?
C37 N38 1.3193(15) . ?
C37 H37 0.987(15) . ?
N38 C39 1.3651(15) . ?
C4 N4 1.3398(15) . ?
N4 C40 1.4053(14) . ?
N4 H4 0.913(16) . ?
C40 C41 1.3742(16) . ?
C40 C49 1.4305(15) . ?
C41 C42 1.4126(17) . ?
C41 H41 0.952(16) . ?
C42 C43 1.3644(18) . ?
C42 H42 0.963(16) . ?
C43 C44 1.4172(16) . ?
C43 H43 0.973(16) . ?
C44 C45 1.4153(16) . ?
C44 C49 1.4170(15) . ?
C45 C46 1.3666(17) . ?
C45 H45 0.980(15) . ?
C46 C47 1.4064(17) . ?
C46 H46 0.994(16) . ?
C47 N48 1.3213(15) . ?
C47 H47 0.983(16) . ?
N48 C49 1.3639(14) . ?
O1W H1W2 0.87(2) . ?
O1W H1W1 0.91(2) . ?
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
O1 C1 C2 O2 -5.1(3) . . . . ?
C4 C1 C2 O2 175.59(16) . . . . ?
O1 C1 C2 C3 176.42(15) . . . . ?
C4 C1 C2 C3 -2.84(9) . . . . ?
O2 C2 C3 N3 3.9(3) . . . . ?
C1 C2 C3 N3 -177.78(15) . . . . ?
O2 C2 C3 C4 -175.36(17) . . . . ?
C1 C2 C3 C4 2.98(9) . . . . ?
C4 C3 N3 C30 -163.00(12) . . . . ?
C2 C3 N3 C30 18.0(2) . . . . ?
C3 N3 C30 C31 14.27(19) . . . . ?
C3 N3 C30 C39 -167.53(11) . . . . ?
N3 C30 C31 C32 -179.30(11) . . . . ?
C39 C30 C31 C32 2.57(18) . . . . ?
C30 C31 C32 C33 -0.95(19) . . . . ?
C31 C32 C33 C34 -0.28(19) . . . . ?
C32 C33 C34 C35 -179.77(12) . . . . ?
C32 C33 C34 C39 -0.13(18) . . . . ?
C33 C34 C35 C36 179.13(12) . . . . ?
C39 C34 C35 C36 -0.52(18) . . . . ?
C34 C35 C36 C37 -0.6(2) . . . . ?
C35 C36 C37 N38 1.2(2) . . . . ?
C36 C37 N38 C39 -0.62(19) . . . . ?
C37 N38 C39 C34 -0.61(17) . . . . ?
C37 N38 C39 C30 179.18(11) . . . . ?
C35 C34 C39 N38 1.17(17) . . . . ?
C33 C34 C39 N38 -178.50(11) . . . . ?
C35 C34 C39 C30 -178.63(11) . . . . ?
C33 C34 C39 C30 1.71(17) . . . . ?
C31 C30 C39 N38 177.26(11) . . . . ?
N3 C30 C39 N38 -1.00(16) . . . . ?
C31 C30 C39 C34 -2.94(17) . . . . ?
N3 C30 C39 C34 178.81(10) . . . . ?
N3 C3 C4 N4 -1.5(2) . . . . ?
C2 C3 C4 N4 177.79(12) . . . . ?
N3 C3 C4 C1 177.64(13) . . . . ?
C2 C3 C4 C1 -3.03(10) . . . . ?
O1 C1 C4 N4 2.8(3) . . . . ?
C2 C1 C4 N4 -177.98(15) . . . . ?
O1 C1 C4 C3 -176.23(16) . . . . ?
C2 C1 C4 C3 2.98(9) . . . . ?
C3 C4 N4 C40 173.96(11) . . . . ?
C1 C4 N4 C40 -4.8(2) . . . . ?
C4 N4 C40 C41 -6.45(19) . . . . ?
C4 N4 C40 C49 175.40(11) . . . . ?
N4 C40 C41 C42 -178.51(11) . . . . ?
C49 C40 C41 C42 -0.43(18) . . . . ?
C40 C41 C42 C43 1.0(2) . . . . ?
C41 C42 C43 C44 -0.57(19) . . . . ?
C42 C43 C44 C45 178.86(12) . . . . ?
C42 C43 C44 C49 -0.48(17) . . . . ?
C49 C44 C45 C46 0.18(17) . . . . ?
C43 C44 C45 C46 -179.18(11) . . . . ?
C44 C45 C46 C47 -0.78(18) . . . . ?
C45 C46 C47 N48 0.7(2) . . . . ?
C46 C47 N48 C49 0.09(19) . . . . ?
C47 N48 C49 C44 -0.75(17) . . . . ?
C47 N48 C49 C40 178.21(11) . . . . ?
C45 C44 C49 N48 0.62(17) . . . . ?
C43 C44 C49 N48 -179.99(11) . . . . ?
C45 C44 C49 C40 -178.32(10) . . . . ?
C43 C44 C49 C40 1.07(16) . . . . ?
C41 C40 C49 N48 -179.60(11) . . . . ?
N4 C40 C49 N48 -1.36(15) . . . . ?
C41 C40 C49 C44 -0.61(16) . . . . ?
N4 C40 C49 C44 177.64(10) . . . . ?
