#------------------------------------------------------------------------------
#$Date: 2023-06-29 12:16:13 +0300 (Thu, 29 Jun 2023) $
#$Revision: 284567 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/93/1569316.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_1569316
loop_
_publ_author_name
'García-Romero, Álvaro'
'Miguel, Daniel'
'Wright, Dominic S.'
'Álvarez, Celedonio M'
'García-Rodríguez, Raúl'
_publ_section_title
;
 Structural and dimensional control of porphyrin capsules using Group 15
 tris(3-pyridyl) linkers.
;
_journal_issue                   24
_journal_name_full               'Chemical science'
_journal_page_first              6522
_journal_page_last               6530
_journal_paper_doi               10.1039/d3sc02151c
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C20 H17 Cl2 N4 Sb'
_chemical_formula_sum            'C20 H17 Cl2 N4 Sb'
_chemical_formula_weight         506.02
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-08-10 deposited with the CCDC.	2023-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.385(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.8444(6)
_cell_length_b                   7.4353(4)
_cell_length_c                   14.6876(8)
_cell_measurement_reflns_used    1896
_cell_measurement_temperature    293
_cell_measurement_theta_max      25.3280
_cell_measurement_theta_min      3.9630
_cell_volume                     1031.41(11)
_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    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 10.4757
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.849
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  18.00   1.00   18.31    --  -10.48 -77.00 -60.00  105
  2  ω     69.00  99.00   1.00   18.31    --   12.36-178.00 -90.00   30
  3  ω     40.00 100.00   1.00   18.31    --   12.36-178.00-180.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5224
_diffrn_reflns_point_group_measured_fraction_full 0.732
_diffrn_reflns_point_group_measured_fraction_max 0.582
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.479
_diffrn_reflns_theta_min         3.487
_exptl_absorpt_coefficient_mu    1.608
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98180
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.085
_refine_diff_density_max         1.098
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.101
_refine_ls_abs_structure_details
;
 Flack x determined using 770 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3348
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0376
_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)+(0.0254P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0685
_refine_ls_wR_factor_ref         0.0773
_reflns_Friedel_coverage         0.370
_reflns_Friedel_fraction_full    0.465
_reflns_Friedel_fraction_max     0.315
_reflns_number_gt                2908
_reflns_number_total             3348
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc02151c2.cif
_cod_data_source_block           3Py
_cod_database_code               1569316
_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.
;
_shelx_estimated_absorpt_t_max   0.875
_shelx_estimated_absorpt_t_min   0.794
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12),
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, 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
Sb1 Sb 0.49861(12) 0.26289(6) 0.50746(9) 0.03482(13) Uani 1 1 d . . . . .
Cl1 Cl 0.6179(3) 0.5182(3) 0.60221(16) 0.0499(6) Uani 1 1 d . . . . .
Cl2 Cl 0.3907(2) 0.0174(3) 0.39816(16) 0.0488(6) Uani 1 1 d . . . . .
N1 N 0.9455(7) 0.1547(11) 0.5239(5) 0.0545(19) Uani 1 1 d . . . . .
N2 N 0.2840(8) -0.0092(13) 0.6902(6) 0.075(3) Uani 1 1 d . . . . .
N3 N 0.1336(10) 0.5993(12) 0.5027(5) 0.066(3) Uani 1 1 d . . . . .
N4 N 0.5455(8) 0.4091(9) 0.3706(4) 0.0401(17) Uani 1 1 d . . . . .
C1 C 0.7006(8) 0.1403(11) 0.5215(5) 0.0350(18) Uani 1 1 d . . . . .
C2 C 0.8189(9) 0.2328(11) 0.5146(6) 0.0414(19) Uani 1 1 d . . . . .
H2 H 0.810703 0.355839 0.502967 0.050 Uiso 1 1 calc R U . . .
C3 C 0.9526(9) -0.0228(12) 0.5413(7) 0.052(2) Uani 1 1 d . . . . .
H3 H 1.038903 -0.080322 0.548536 0.062 Uiso 1 1 calc R U . . .
C4 C 0.8402(9) -0.1242(12) 0.5489(7) 0.052(2) Uani 1 1 d . . . . .
H4 H 0.850030 -0.247210 0.560169 0.062 Uiso 1 1 calc R U . . .
C5 C 0.7141(9) -0.0415(11) 0.5396(6) 0.045(2) Uani 1 1 d . . . . .
H5 H 0.636837 -0.107601 0.545561 0.054 Uiso 1 1 calc R U . . .
C6 C 0.4553(10) 0.1358(11) 0.6267(6) 0.039(2) Uani 1 1 d . . . . .
C7 C 0.5560(9) 0.1075(13) 0.7108(6) 0.050(2) Uani 1 1 d . . . . .
H7 H 0.648632 0.144890 0.718222 0.060 Uiso 1 1 calc R U . . .
C8 C 0.5210(10) 0.0239(13) 0.7845(6) 0.052(2) Uani 1 1 d . . . . .
H8 H 0.589138 0.004993 0.842087 0.062 Uiso 1 1 calc R U . . .
C9 C 0.3856(13) -0.0304(14) 0.7718(7) 0.067(3) Uani 1 1 d . . . . .
H9 H 0.362216 -0.085162 0.822267 0.080 Uiso 1 1 calc R U . . .
C10 C 0.3211(10) 0.0728(14) 0.6207(6) 0.057(3) Uani 1 1 d . . . . .
H10 H 0.251496 0.089021 0.563492 0.068 Uiso 1 1 calc R U . . .
C11 C 0.3040(9) 0.4101(10) 0.4594(5) 0.038(2) Uani 1 1 d . . . . .
C12 C 0.2600(11) 0.5146(12) 0.5228(6) 0.053(2) Uani 1 1 d . . . . .
H12 H 0.321206 0.528017 0.583475 0.063 Uiso 1 1 calc R U . . .
C13 C 0.0500(12) 0.5762(14) 0.4148(7) 0.067(3) Uani 1 1 d . . . . .
H13 H -0.039548 0.628158 0.399319 0.080 Uiso 1 1 calc R U . . .
C14 C 0.0866(11) 0.4824(13) 0.3465(6) 0.058(3) Uani 1 1 d . . . . .
H14 H 0.025544 0.475855 0.285412 0.070 Uiso 1 1 calc R U . . .
C15 C 0.2152(10) 0.3969(12) 0.3687(6) 0.051(2) Uani 1 1 d . . . . .
H15 H 0.242091 0.330760 0.322894 0.061 Uiso 1 1 calc R U . . .
C16 C 0.5322(10) 0.5852(11) 0.3600(6) 0.050(2) Uani 1 1 d . . . . .
H16 H 0.504415 0.651678 0.405275 0.060 Uiso 1 1 calc R U . . .
C17 C 0.5581(12) 0.6745(13) 0.2841(7) 0.065(3) Uani 1 1 d . . . . .
H17 H 0.549681 0.798900 0.279165 0.078 Uiso 1 1 calc R U . . .
C18 C 0.5965(11) 0.5769(14) 0.2162(6) 0.056(3) Uani 1 1 d . . . . .
H18 H 0.610095 0.633111 0.162849 0.067 Uiso 1 1 calc R U . . .
C19 C 0.6140(10) 0.3976(13) 0.2282(6) 0.051(2) Uani 1 1 d . . . . .
H19 H 0.644238 0.329350 0.184543 0.061 Uiso 1 1 calc R U . . .
C20 C 0.5872(9) 0.3170(12) 0.3048(6) 0.045(2) Uani 1 1 d . . . . .
H20 H 0.598406 0.193103 0.311666 0.054 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'
Cl Cl 0.1484 0.1585 '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'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -5 1 0.0281
3 5 -1 0.0581
1 0 5 0.0667
-1 0 -5 0.0667
5 -3 -4 0.0427
-5 3 4 0.0427
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
Cl1 Sb1 Cl2 173.54(11) . . ?
N4 Sb1 Cl1 87.20(17) . . ?
N4 Sb1 Cl2 86.58(18) . . ?
C1 Sb1 Cl1 89.5(2) . . ?
C1 Sb1 Cl2 88.0(2) . . ?
C1 Sb1 N4 83.3(3) . . ?
C1 Sb1 C11 165.1(3) . . ?
C6 Sb1 Cl1 93.0(2) . . ?
C6 Sb1 Cl2 93.3(2) . . ?
C6 Sb1 N4 179.4(3) . . ?
C6 Sb1 C1 97.3(3) . . ?
C6 Sb1 C11 97.4(3) . . ?
C11 Sb1 Cl1 91.8(2) . . ?
C11 Sb1 Cl2 89.0(2) . . ?
C11 Sb1 N4 82.0(3) . . ?
C3 N1 C2 116.1(7) . . ?
C10 N2 C9 116.5(8) . . ?
C13 N3 C12 115.5(8) . . ?
C16 N4 Sb1 120.3(5) . . ?
C16 N4 C20 117.5(7) . . ?
C20 N4 Sb1 122.3(5) . . ?
C2 C1 Sb1 124.1(6) . . ?
C5 C1 Sb1 118.1(6) . . ?
C5 C1 C2 117.8(8) . . ?
N1 C2 C1 123.6(8) . . ?
N1 C2 H2 118.2 . . ?
C1 C2 H2 118.2 . . ?
N1 C3 H3 118.1 . . ?
N1 C3 C4 123.8(8) . . ?
C4 C3 H3 118.1 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.7(8) . . ?
C5 C4 H4 120.7 . . ?
C1 C5 H5 120.0 . . ?
C4 C5 C1 119.9(8) . . ?
C4 C5 H5 120.0 . . ?
C7 C6 Sb1 123.3(7) . . ?
C7 C6 C10 116.3(8) . . ?
C10 C6 Sb1 120.4(6) . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.3(8) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 120.6 . . ?
C9 C8 C7 118.8(8) . . ?
C9 C8 H8 120.6 . . ?
N2 C9 C8 123.2(8) . . ?
N2 C9 H9 118.4 . . ?
C8 C9 H9 118.4 . . ?
N2 C10 C6 125.0(8) . . ?
N2 C10 H10 117.5 . . ?
C6 C10 H10 117.5 . . ?
C12 C11 Sb1 119.2(6) . . ?
C12 C11 C15 117.5(8) . . ?
C15 C11 Sb1 123.2(6) . . ?
N3 C12 C11 124.3(9) . . ?
N3 C12 H12 117.9 . . ?
C11 C12 H12 117.9 . . ?
N3 C13 H13 117.8 . . ?
N3 C13 C14 124.4(10) . . ?
C14 C13 H13 117.8 . . ?
C13 C14 H14 120.5 . . ?
C13 C14 C15 119.0(9) . . ?
C15 C14 H14 120.5 . . ?
C11 C15 H15 120.4 . . ?
C14 C15 C11 119.3(8) . . ?
C14 C15 H15 120.4 . . ?
N4 C16 H16 118.8 . . ?
N4 C16 C17 122.5(8) . . ?
C17 C16 H16 118.8 . . ?
C16 C17 H17 120.5 . . ?
C18 C17 C16 119.0(9) . . ?
C18 C17 H17 120.5 . . ?
C17 C18 H18 120.7 . . ?
C19 C18 C17 118.6(8) . . ?
C19 C18 H18 120.7 . . ?
C18 C19 H19 120.2 . . ?
C18 C19 C20 119.6(8) . . ?
C20 C19 H19 120.2 . . ?
N4 C20 C19 122.7(8) . . ?
N4 C20 H20 118.6 . . ?
C19 C20 H20 118.6 . . ?
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
Sb1 Cl1 2.449(2) . ?
Sb1 Cl2 2.465(2) . ?
Sb1 N4 2.441(6) . ?
Sb1 C1 2.144(8) . ?
Sb1 C6 2.136(8) . ?
Sb1 C11 2.146(8) . ?
N1 C2 1.347(10) . ?
N1 C3 1.342(11) . ?
N2 C9 1.335(13) . ?
N2 C10 1.326(11) . ?
N3 C12 1.351(12) . ?
N3 C13 1.332(13) . ?
N4 C16 1.321(10) . ?
N4 C20 1.340(10) . ?
C1 C2 1.380(11) . ?
C1 C5 1.377(11) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.369(12) . ?
C4 H4 0.9300 . ?
C4 C5 1.357(11) . ?
C5 H5 0.9300 . ?
C6 C7 1.365(11) . ?
C6 C10 1.380(12) . ?
C7 H7 0.9300 . ?
C7 C8 1.373(11) . ?
C8 H8 0.9300 . ?
C8 C9 1.355(14) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.374(11) . ?
C11 C15 1.375(11) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.351(12) . ?
C14 H14 0.9300 . ?
C14 C15 1.371(12) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.381(12) . ?
C17 H17 0.9300 . ?
C17 C18 1.369(12) . ?
C18 H18 0.9300 . ?
C18 C19 1.350(13) . ?
C19 H19 0.9300 . ?
C19 C20 1.365(11) . ?
C20 H20 0.9300 . ?
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
Sb1 N4 C16 C17 179.7(8) . . . . ?
Sb1 N4 C20 C19 -179.8(7) . . . . ?
Sb1 C1 C2 N1 179.7(6) . . . . ?
Sb1 C1 C5 C4 179.9(7) . . . . ?
Sb1 C6 C7 C8 -179.6(7) . . . . ?
Sb1 C6 C10 N2 179.4(9) . . . . ?
Sb1 C11 C12 N3 -173.5(8) . . . . ?
Sb1 C11 C15 C14 173.8(7) . . . . ?
N1 C3 C4 C5 -0.8(16) . . . . ?
N3 C13 C14 C15 3.2(17) . . . . ?
N4 C16 C17 C18 1.3(16) . . . . ?
C2 N1 C3 C4 0.5(14) . . . . ?
C2 C1 C5 C4 -0.9(13) . . . . ?
C3 N1 C2 C1 -0.4(12) . . . . ?
C3 C4 C5 C1 1.0(14) . . . . ?
C5 C1 C2 N1 0.6(12) . . . . ?
C6 C7 C8 C9 0.4(15) . . . . ?
C7 C6 C10 N2 1.1(16) . . . . ?
C7 C8 C9 N2 1.0(17) . . . . ?
C9 N2 C10 C6 0.2(17) . . . . ?
C10 N2 C9 C8 -1.3(17) . . . . ?
C10 C6 C7 C8 -1.4(14) . . . . ?
C12 N3 C13 C14 -2.8(17) . . . . ?
C12 C11 C15 C14 -2.1(13) . . . . ?
C13 N3 C12 C11 -0.2(15) . . . . ?
C13 C14 C15 C11 -0.6(15) . . . . ?
C15 C11 C12 N3 2.5(14) . . . . ?
C16 N4 C20 C19 -0.9(13) . . . . ?
C16 C17 C18 C19 -3.1(16) . . . . ?
C17 C18 C19 C20 2.9(15) . . . . ?
C18 C19 C20 N4 -1.0(15) . . . . ?
C20 N4 C16 C17 0.7(14) . . . . ?
