Thymine functionalised porphyrins, synthesis and heteromolecular surface-based self-assembly
Slater, Anna G.; Hu, Ya; Yang, Lixu; Argent, Stephen P.; Lewis, William; Blunt, Matthew O.; Champness, Neil R.; Chem. Sci. 6 (2015) 1562–; doi:10.1039/C4SC03531C

data_1518408
_publ_section_title
;
 Thymine functionalised porphyrins, synthesis and heteromolecular
 surface-based self-assembly
;
_journal_issue                   2
_journal_name_full               'Chem. Sci.'
_journal_page_first              1562
_journal_paper_doi               10.1039/C4SC03531C
_journal_volume                  6
_journal_year                    2015
_chemical_formula_moiety         'C80 H86 N6 O3, 3(C H Cl3)'
_chemical_formula_sum            'C86 H92 Cl18 N6 O3'
_chemical_formula_weight         1895.75
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_audit_update_record
;
2014-11-14 deposited with the CCDC.
2014-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                92.068(2)
_cell_angle_beta                 110.731(3)
_cell_angle_gamma                99.280(3)
_cell_formula_units_Z            2
_cell_length_a                   15.4721(5)
_cell_length_b                   16.3717(5)
_cell_length_c                   19.0278(6)
_cell_measurement_reflns_used    20679
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      75.3542
_cell_measurement_theta_min      3.1961
_cell_volume                     4426.0(3)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46)'
_computing_data_collection
'CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46)'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.3613
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -96.00  -69.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.7877  125.0000  -60.0000 27

  2 omega  -11.00   72.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       43.7877  -77.0000  -30.0000 83

  3 omega   49.00  114.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       43.7877   38.0000 -120.0000 65

  4 omega    9.00   64.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       43.7877  -57.0000  120.0000 55

  5 omega   11.00  112.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       43.7877   19.0000  150.0000 101

  6 omega   33.00   69.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000 -180.0000 36

  7 omega   37.00   68.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000  -60.0000 31

  8 omega  110.00  152.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   30.0000 -180.0000 42

  9 omega   32.00  146.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -15.0000  -30.0000 114

 10 omega   38.00   89.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -95.0000   90.0000 51

 11 omega   36.00   66.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000  150.0000 30

 12 omega   35.00  101.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -95.0000  -30.0000 66

 13 omega   48.00  136.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -77.0000  150.0000 88

 14 omega   41.00   66.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000  150.0000 25

 15 omega   40.00   75.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000    0.0000 35

 16 omega   36.00   67.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000  -60.0000 31

 17 omega   38.00  122.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472 -125.0000  -30.0000 84

 18 omega   37.00   69.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000 -150.0000 32

 19 omega   34.00   69.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000   90.0000 35

 20 omega   55.00  121.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472 -125.0000 -180.0000 66

 21 omega   47.00  109.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -95.0000   30.0000 62

 22 omega   95.00  143.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   30.0000  -30.0000 48

 23 omega   38.00   77.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000   60.0000 39

 24 omega   83.00  118.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   45.0000   30.0000 35

 25 omega   54.00  106.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472 -125.0000  -90.0000 52

 26 omega   14.00  115.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       43.7877   77.0000  150.0000 101

 27 omega   14.00  115.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       43.7877   77.0000   60.0000 101

 28 omega   14.00  115.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       43.7877   77.0000  -30.0000 101

 29 omega  -25.00   69.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       43.7877  -57.0000   60.0000 94

 30 omega   19.00  112.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       43.7877   57.0000  -90.0000 93

 31 omega   83.00  158.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   45.0000   60.0000 75

 32 omega   83.00  158.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   45.0000  120.0000 75

 33 omega   76.00  121.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   77.0000  150.0000 45

 34 omega   80.00  158.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   61.0000  -30.0000 78
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0181544000
_diffrn_orient_matrix_UB_12      0.0092902000
_diffrn_orient_matrix_UB_13      0.0851492000
_diffrn_orient_matrix_UB_21      -0.0065554000
_diffrn_orient_matrix_UB_22      -0.0947800000
_diffrn_orient_matrix_UB_23      0.0014855000
_diffrn_orient_matrix_UB_31      0.1066259000
_diffrn_orient_matrix_UB_32      0.0107256000
_diffrn_orient_matrix_UB_33      0.0178532000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            52160
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_min         3.199
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.516
_exptl_absorpt_correction_T_max  0.569
_exptl_absorpt_correction_T_min  0.157
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
'CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Numerical absorption correction based on gaussian integration over a multifaceted crystal model'
_exptl_crystal_colour            'clear violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1960
_exptl_crystal_size_max          0.6697
_exptl_crystal_size_mid          0.4973
_exptl_crystal_size_min          0.4106
_refine_diff_density_max         1.899
_refine_diff_density_min         -1.323
_refine_diff_density_rms         0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.579
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     948
_refine_ls_number_reflns         15638
_refine_ls_number_restraints     1961
_refine_ls_restrained_S_all      1.589
_refine_ls_R_factor_all          0.1406
_refine_ls_R_factor_gt           0.1220
_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/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3579
_refine_ls_wR_factor_ref         0.3846
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12017
_reflns_number_total             15638
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4sc03531c2.cif
_cod_data_source_block           porasa_sq
_cod_depositor_comments
'Adding full bibliography for 1518407--1518408.cif.'
_cod_database_code               1518408
_nottingham_internal_coll_name   PORASA
_nottingham_internal_coll_number 11257
_nottingham_internal_coll_client AS/NRC
_nottingham_internal_coll_type   CUSTOM
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time '11.0000, 44.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_user   pczspa
_nottingham_internal_coll_date   29/05/2012
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_date 31/05/2012
_nottingham_internal_process_user pczspa
_nottingham_internal_solution_date 31/05/2012
_nottingham_internal_solution_user pczspa
_nottingham_internal_refinement_date 04/07/2014
_nottingham_internal_refinement_user pczspa
_nottingham_internal_self_validation_user pczspa
_platon_squeeze_void_probe_radius 1.20
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C85 H94 N6 O4 Cl12'
_chemical_oxdiff_usercomment
'PORASA #11257 IN FOMBLIN FILM ON MICROMOUNT FOR AS/NRC'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C85-C75 \\sim C81-C73 \\sim C65-C55 \\sim C61-C53 \\sim C45-C35 \\sim C41-C33
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{C41, C42, C43, C44}
{C41, C42, C44, C43}
{C41, C44, C43, C42}
as
{C45, C46, C47, C48}
{C41, C42, C43, C44}
{C41, C42, C44, C43}
{C41, C44, C43, C42}
as
{C61, C62, C63, C64}
{C41, C42, C43, C44}
{C41, C42, C44, C43}
{C41, C44, C43, C42}
as
{C65, C66, C67, C68}
{C41, C42, C43, C44}
{C41, C42, C44, C43}
{C41, C44, C43, C42}
as
{C81, C82, C83, C84}
{C41, C42, C43, C44}
{C41, C42, C44, C43}
{C41, C44, C43, C42}
as
{C85, C86, C87, C88}
{C1A, Cl2A, Cl3A, Cl4A}
{C1A, Cl2A, Cl3A, Cl4A}
{C1A, Cl4A, Cl3A, Cl2A}
as
{C1B, Cl2B, Cl3B, Cl4B}
{C1A, Cl2A, Cl3A, Cl4A}
{C1A, Cl2A, Cl3A, Cl4A}
{C1A, Cl4A, Cl3A, Cl2A}
as
{C1C, Cl2C, Cl3C, Cl4C}
{C1A, Cl2A, Cl3A, Cl4A}
{C1A, Cl2A, Cl3A, Cl4A}
{C1A, Cl4A, Cl3A, Cl2A}
as
{C1D, Cl2D, Cl3D, Cl4D}
6. Others
 Sof(C1D)=Sof(H1D)=Sof(Cl2D)=Sof(Cl3D)=Sof(Cl4D)=1-FVAR(1)
 Sof(C1C)=Sof(H1C)=Sof(Cl2C)=Sof(Cl3C)=Sof(Cl4C)=FVAR(1)
 Fixed Sof: H21(0.5) H22(0.5) H23(0.5) H24(0.5)
7.a Ternary CH refined with riding coordinates:
 C1A(H1A), C1B(H1B), C1C(H1C), C1D(H1D)
7.b Me refined with riding coordinates:
 C43(H43A,H43B,H43C), C42(H42A,H42B,H42C), C46(H46A,H46B,H46C), C47(H47A,H47B,
 H47C), C48(H48A,H48B,H48C), C62(H62A,H62B,H62C), C63(H63A,H63B,H63C), C64(H64A,
 H64B,H64C), C66(H66A,H66B,H66C), C67(H67A,H67B,H67C), C68(H68A,H68B,H68C),
 C82(H82A,H82B,H82C), C83(H83A,H83B,H83C), C84(H84A,H84B,H84C), C86(H86A,H86B,
 H86C), C87(H87A,H87B,H87C), C88(H88A,H88B,H88C), C9T(H9TA,H9TB,H9TC)
7.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C12(H12), C13(H13), C17(H17), C18(H18),
 N21(H21), N22(H22), N23(H23), N24(H24), C32(H32), C34(H34), C36(H36), C52(H52),
  C54(H54), C56(H56), C72(H72), C74(H74), C76(H76), C92(H92), C93(H93),
 C95(H95), C96(H96), C6T(H6T), C13T(H13T), C14T(H14T), C15T(H15T), C16T(H16T),
 C17T(H17T)
7.d Idealised Me refined as rotating group:
 C44(H44A,H44B,H44C)
;
_shelx_res_checksum              12099
_shelx_fab_checksum              20450
_olex2_exptl_crystal_mounting_method 'micromount in fomblin'
_olex2_submission_special_instructions 'No special instructions were received'