Supramolecular chirogenesis in zinc porphyrins by enantiopure hemicucurbit[n]urils (n = 6, 8)
Ustrnul, Lukaš; Kaabel, Sandra; Burankova, Tatsiana; Martõnova, Jevgenija; Adamson, Jasper; Konrad, Nele; Burk, Peeter; Borovkov, Victor; Aav, Riina; Chemical Communications  (2019) –; doi:10.1039/C9CC07150D

data_7124507
_publ_section_title
;
 Supramolecular chirogenesis in zinc porphyrins by enantiopure
 hemicucurbit[n]urils (n = 6, 8)
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC07150D
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C184 H200 N32 O12 Zn2, C H4 O, H2 O'
_chemical_formula_sum            'C185 H206 N32 O14 Zn2'
_chemical_formula_weight         3232.55
_chemical_name_common
;
cyclohexanohemicucurbit[6]uril complex with zinc tetraphenylporphyrin
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-08-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-27 deposited with the CCDC.	2019-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                85.237(2)
_cell_angle_beta                 77.006(2)
_cell_angle_gamma                85.321(2)
_cell_formula_units_Z            1
_cell_length_a                   12.8590(3)
_cell_length_b                   13.8291(4)
_cell_length_c                   24.3771(6)
_cell_measurement_reflns_used    12354
_cell_measurement_temperature    123
_cell_measurement_theta_max      66.3200
_cell_measurement_theta_min      1.8570
_cell_volume                     4200.51(19)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection
;
Rigaku CollectionStrategy through HKL-3000 program package
Minor, W., Cymborowski, M., Otwinowski, Z., Chruszcz, M. (2011) 
Acta Cryst. D62, 859-866
;
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics
;
Mercury CSD 3.10 (Macrae, C. F., et al. (2006). J. Appl. Cryst. 39, 453-457)
POV-Ray 3.7 (Persistence of Vision Pty. Ltd. (2004)) 
;
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 22.17
_diffrn_detector_type            Saturn944+
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -179.00   0.00   1.00   60.00    --  -90.00  60.00 108.00  179
  2  \w   -110.00  69.00   1.00   15.00    --  -21.00  60.00-180.00  179
  3  \w   -179.00   0.00   1.00   60.00    --  -90.00  30.00 -36.00  179
  4  \w   -179.00   0.00   1.00   60.00    --  -90.00  60.00-180.00  179
  5  \w   -179.00   0.00   1.00   60.00    --  -90.00  60.00  36.00  179
  6  \w   -179.00   0.00   1.00   60.00    --  -90.00  60.00-108.00  179
  7  \w   -179.00   0.00   1.00   60.00    --  -90.00  30.00-180.00  179
  8  \w   -179.00   0.00   1.00   60.00    --  -90.00  30.00  36.00  179
;
_diffrn_measurement_device       AFC11
_diffrn_measurement_device_type  'Rigaku Saturn944+ (2x2 bin mode)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0021840000
_diffrn_orient_matrix_UB_12      -0.0069934000
_diffrn_orient_matrix_UB_13      -0.0629975000
_diffrn_orient_matrix_UB_21      -0.0758952000
_diffrn_orient_matrix_UB_22      -0.0834912000
_diffrn_orient_matrix_UB_23      0.0153037000
_diffrn_orient_matrix_UB_31      -0.0970366000
_diffrn_orient_matrix_UB_32      0.0743584000
_diffrn_orient_matrix_UB_33      0.0047345000
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_unetI/netI     0.0851
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            45280
_diffrn_reflns_point_group_measured_fraction_full 0.774
_diffrn_reflns_point_group_measured_fraction_max 0.774
_diffrn_reflns_theta_full        67.344
_diffrn_reflns_theta_max         67.344
_diffrn_reflns_theta_min         1.864
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Rigaku MicroMax-003'
_exptl_absorpt_coefficient_mu    0.932
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light pink'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.661
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 5215 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2268
_refine_ls_number_reflns         23390
_refine_ls_number_restraints     579
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0600
_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/[\s^2^(Fo^2^)+(0.0758P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1419
_refine_ls_wR_factor_ref         0.1562
_reflns_Friedel_coverage         0.598
_reflns_Friedel_fraction_full    0.579
_reflns_Friedel_fraction_max     0.579
_reflns_number_gt                19174
_reflns_number_total             23390
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07150d5.cif
_cod_data_source_block           R-cycHC6_ZnTPP
_cod_database_code               7124507
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C48 H72 N12 O6'
_shelx_estimated_absorpt_t_max   0.946
_shelx_estimated_absorpt_t_min   0.921
_reflns_odcompleteness_completeness 96.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.23
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained planarity
 C25K, C26K, C27K, C28K, C29K, C30K
 with sigma of 0.1
 C25J, C26J, C27J, C28J, C29J, C30J
 with sigma of 0.1
 C14J, C15J, C16J, C17J, C18J, C19J
 with sigma of 0.1
 C14K, C15K, C16K, C17K, C18K, C19K
 with sigma of 0.1
3. Uiso/Uaniso restraints and constraints
C25X \\sim C26X \\sim C27X \\sim C28X \\sim C29X \\sim C30X \\sim C25Y \\sim
C26Y \\sim C27Y \\sim C28Y \\sim C29Y \\sim C30Y: within 1.7A with sigma of
0.02 and sigma for terminal atoms of 0.04
C1S \\sim O1S: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.04
C25J \\sim C26J \\sim C27J \\sim C28J \\sim C29J \\sim C30J \\sim C25K \\sim
C26K \\sim C27K \\sim C28K \\sim C29K \\sim C30K: within 1.7A with sigma of
0.02 and sigma for terminal atoms of 0.04
C14J \\sim C15J \\sim C16J \\sim C17J \\sim C18J \\sim C19J \\sim C14K \\sim
C15K \\sim C16K \\sim C17K \\sim C18K \\sim C19K: within 1.7A with sigma of
0.02 and sigma for terminal atoms of 0.04
4. Same fragment restrains
{C14J, C15J, C16J, C17J, C18J, C19J} sigma for 1-2: 0.02, 1-3: 0.04
as
{C14K, C15K, C16K, C17K, C18K, C19K}
{C25J, C26J, C27J, C28J, C29J, C30J} sigma for 1-2: 0.02, 1-3: 0.04
as
{C25K, C26K, C27K, C28K, C29K, C30K}
{C25X, C26X, C27X, C28X, C29X, C30X} sigma for 1-2: 0.02, 1-3: 0.04
as
{C25Y, C26Y, C27Y, C28Y, C29Y, C30Y}
5. Others
 Sof(C25Y)=Sof(C26Y)=Sof(H26Y)=Sof(C27Y)=Sof(H27Y)=Sof(C28Y)=Sof(H28Y)=
 Sof(C29Y)=Sof(H29Y)=Sof(C30Y)=Sof(H30Y)=1-FVAR(1)
 Sof(C25X)=Sof(C26X)=Sof(H26X)=Sof(C27X)=Sof(H27X)=Sof(C28X)=Sof(H28X)=
 Sof(C29X)=Sof(H29X)=Sof(C30X)=Sof(H30X)=FVAR(1)
 Sof(C14K)=Sof(C15K)=Sof(H15K)=Sof(C16K)=Sof(H16K)=Sof(C17K)=Sof(H17K)=
 Sof(C18K)=Sof(H18K)=Sof(C19K)=Sof(H19K)=1-FVAR(2)
 Sof(C14J)=Sof(C15J)=Sof(H15J)=Sof(C16J)=Sof(H16J)=Sof(C17J)=Sof(H17J)=
 Sof(C18J)=Sof(H18J)=Sof(C19J)=Sof(H19J)=FVAR(2)
 Sof(C25K)=Sof(C26K)=Sof(H26K)=Sof(C27K)=Sof(H27K)=Sof(C28K)=Sof(H28K)=
 Sof(C29K)=Sof(H29K)=Sof(C30K)=Sof(H30K)=1-FVAR(3)
 Sof(C25J)=Sof(C26J)=Sof(H26J)=Sof(C27J)=Sof(H27J)=Sof(C28J)=Sof(H28J)=
 Sof(C29J)=Sof(H29J)=Sof(C30J)=Sof(H30J)=FVAR(3)
6.a Free rotating group:
 O1W(H1WA,H1WB)
6.b Ternary CH refined with riding coordinates:
 C1A(H1A), C2A(H2A), C1B(H1B), C2B(H2B), C1C(H1C), C2C(H2C), C1D(H1D),
 C2D(H2D), C1E(H1E), C2E(H2E), C1F(H1F), C2F(H2F), C1G(H1G), C2G(H2G), C1H(H1H),
  C2H(H2H), C1I(H1I), C2I(H2I), C1J(H1J), C2J(H2J), C1K(H1K), C2K(H2K),
 C1L(H1L), C2L(H2L)
6.c Secondary CH2 refined with riding coordinates:
 C3A(H3AA,H3AB), C4A(H4AA,H4AB), C5A(H5AA,H5AB), C6A(H6AA,H6AB), C8A(H8AA,
 H8AB), C3B(H3BA,H3BB), C4B(H4BA,H4BB), C5B(H5BA,H5BB), C6B(H6BA,H6BB),
 C8B(H8BA,H8BB), C3C(H3CA,H3CB), C4C(H4CA,H4CB), C5C(H5CA,H5CB), C6C(H6CA,H6CB),
  C8C(H8CA,H8CB), C3D(H3DA,H3DB), C4D(H4DA,H4DB), C5D(H5DA,H5DB), C6D(H6DA,
 H6DB), C8D(H8DA,H8DB), C3E(H3EA,H3EB), C4E(H4EA,H4EB), C5E(H5EA,H5EB),
 C6E(H6EA,H6EB), C8E(H8EA,H8EB), C3F(H3FA,H3FB), C4F(H4FA,H4FB), C5F(H5FA,H5FB),
  C6F(H6FA,H6FB), C8F(H8FA,H8FB), C3G(H3GA,H3GB), C4G(H4GA,H4GB), C5G(H5GA,
 H5GB), C6G(H6GA,H6GB), C8G(H8GA,H8GB), C3H(H3HA,H3HB), C4H(H4HA,H4HB),
 C5H(H5HA,H5HB), C6H(H6HA,H6HB), C8H(H8HA,H8HB), C3I(H3IA,H3IB), C4I(H4IA,H4IB),
  C5I(H5IA,H5IB), C6I(H6IA,H6IB), C8I(H8IA,H8IB), C3J(H3JA,H3JB), C4J(H4JA,
 H4JB), C5J(H5JA,H5JB), C6J(H6JA,H6JB), C8J(H8JA,H8JB), C3K(H3KA,H3KB),
 C4K(H4KA,H4KB), C5K(H5KA,H5KB), C6K(H6KA,H6KB), C8K(H8KA,H8KB), C3L(H3LA,H3LB),
  C4L(H4LA,H4LB), C5L(H5LA,H5LB), C6L(H6LA,H6LB), C8L(H8LA,H8LB)
6.d Aromatic/amide H refined with riding coordinates:
 C10A(H10A), C11A(H11A), C15A(H15A), C16A(H16A), C17A(H17A), C18A(H18A),
 C19A(H19A), C21A(H21A), C22A(H22A), C32A(H32A), C33A(H33A), C37A(H37A),
 C38A(H38A), C39A(H39A), C40A(H40A), C41A(H41A), C43A(H43A), C44A(H44A),
 C48A(H48A), C49A(H49A), C50A(H50A), C51A(H51A), C52A(H52A), C10J(H10J),
 C11J(H11J), C15J(H15J), C16J(H16J), C17J(H17J), C18J(H18J), C19J(H19J),
 C21J(H21J), C22J(H22J), C26J(H26J), C27J(H27J), C28J(H28J), C29J(H29J),
 C30J(H30J), C32J(H32J), C33J(H33J), C37J(H37J), C38J(H38J), C39J(H39J),
 C40J(H40J), C41J(H41J), C43J(H43J), C44J(H44J), C48J(H48J), C49J(H49J),
 C50J(H50J), C51J(H51J), C52J(H52J), C15K(H15K), C16K(H16K), C17K(H17K),
 C18K(H18K), C19K(H19K), C26K(H26K), C27K(H27K), C28K(H28K), C29K(H29K),
 C30K(H30K), C26X(H26X), C27X(H27X), C28X(H28X), C29X(H29X), C30X(H30X),
 C26Y(H26Y), C27Y(H27Y), C28Y(H28Y), C29Y(H29Y), C30Y(H30Y)
6.e Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC)
6.f Idealised tetrahedral OH refined as rotating group:
 O1S(H1S)
;
_shelx_res_checksum              76547
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.925
_oxdiff_exptl_absorpt_empirical_full_min 0.428