#------------------------------------------------------------------------------
#$Date: 2019-08-14 03:26:17 +0300 (Wed, 14 Aug 2019) $
#$Revision: 217514 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/22/1552208.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_1552208
loop_
_publ_author_name
'El Abbassi, Maria'
'Zwick, Patrick'
'Rates, Alfredo'
'Stefani, Davide'
'Prescimone, Alessandro'
'Mayor, Marcel'
'van der Zant, Herre S. J.'
'Dulić, Diana'
_publ_section_title
;
 Unravelling the conductance path through single-porphyrin junctions
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC02497B
_journal_year                    2019
_chemical_compound_source        'Patrick Zwick'
_chemical_formula_moiety         'C60 H62 N4'
_chemical_formula_sum            'C60 H62 N4'
_chemical_formula_weight         839.18
_chemical_melting_point          ?
_chemical_name_systematic
'5,10,15,20-tetrakis-(4-(tert-butyl)phenyl) porphyrin'
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2018-10-26
_audit_creation_method           CRYSTALS_ver_14.61_build_6949
_audit_update_record
;
2019-04-16 deposited with the CCDC.    2019-08-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 133.4200(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.6207(3)
_cell_length_b                   16.2758(3)
_cell_length_c                   15.1875(3)
_cell_measurement_reflns_used    4595
_cell_measurement_temperature    130
_cell_measurement_theta_max      56
_cell_measurement_theta_min      3
_cell_volume                     2445.48(9)
_computing_cell_refinement
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection
;
X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)
;
_computing_data_reduction
;
X-Area Integrate 1.73.1.0 (STOE, 2018)
X-Area X-Red32 1.65.0.0 (STOE, 2018) 
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      130
_diffrn_detector                 Pilatus300K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Stoe StadiVari'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34143
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_av_unetI/netI     0.007
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            38050
_diffrn_reflns_theta_full        54.000
_diffrn_reflns_theta_max         57.187
_diffrn_reflns_theta_min         2.938
_diffrn_source                   'Metaljet D2'
_diffrn_source_current           2.860
_diffrn_source_power             0.200
_diffrn_source_voltage           70
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_T_max  0.9934
_exptl_absorpt_correction_T_min  0.9808
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in
F. R. Ahmed (Editor), "Crystallographic Computing",
Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             900
_exptl_crystal_recrystallization_method
; 
THF / MeOH
;
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4935
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.0002325
_refine_ls_shift/su_mean         0.0000241
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.06P)² + 1.26P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1115
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1115
_reflns_limit_h_max              12
_reflns_limit_h_min              -17
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                4674
_reflns_number_total             4955
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0448
_oxford_refine_ls_scale          0.3078(3)
_oxford_reflns_number_all        4935
_oxford_structure_analysis_title 'ZWP472_130K in P 21/n'
_cod_data_source_file            c9sc02497b2.cif
_cod_data_source_block           ZWP472_130K
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_database_code               1552208
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,-y+1/2,z+1/2
-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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
N1 N -0.67654(9) 0.45293(6) -0.06032(8) 0.0263 1.0000 Uani .
C2 C -0.78421(11) 0.49663(7) -0.09448(10) 0.0268 1.0000 Uani .
C3 C -0.21189(11) 0.41789(7) 0.08419(10) 0.0271 1.0000 Uani .
C4 C -0.31518(11) 0.36293(7) 0.04299(10) 0.0268 1.0000 Uani D
N5 N -0.43477(9) 0.38188(6) 0.01026(9) 0.0261 1.0000 Uani D
C6 C -0.50872(11) 0.31164(7) -0.02310(10) 0.0264 1.0000 Uani D
C7 C -0.63726(11) 0.30540(7) -0.06427(10) 0.0261 1.0000 Uani .
C8 C -0.71587(11) 0.37219(7) -0.08457(10) 0.0262 1.0000 Uani .
C9 C -0.85282(11) 0.36508(7) -0.13600(11) 0.0297 1.0000 Uani .
C10 C -0.89538(11) 0.44168(7) -0.14340(11) 0.0305 1.0000 Uani .
C11 C -0.69238(11) 0.22060(7) -0.08585(10) 0.0275 1.0000 Uani .
C12 C -0.63626(14) 0.16872(8) 0.01170(11) 0.0384 1.0000 Uani .
C13 C -0.68870(15) 0.09088(8) -0.00567(12) 0.0423 1.0000 Uani .
C14 C -0.79902(14) 0.06123(8) -0.12116(12) 0.0355 1.0000 Uani .
C15 C -0.85214(13) 0.11277(8) -0.21859(11) 0.0351 1.0000 Uani .
C16 C -0.80028(12) 0.19067(7) -0.20156(10) 0.0313 1.0000 Uani .
C17 C -0.85567(16) -0.02573(8) -0.14341(13) 0.0445 1.0000 Uani .
C18 C -0.8076(2) -0.07800(9) -0.19085(15) 0.0552 1.0000 Uani .
C19 C -0.8077(2) -0.06442(9) -0.02749(16) 0.0599 1.0000 Uani .
C20 C -1.01179(18) -0.02501(10) -0.23835(17) 0.0619 1.0000 Uani .
C21 C -0.43216(12) 0.24493(7) -0.01195(11) 0.0299 1.0000 Uani .
C22 C -0.31547(12) 0.27620(7) 0.02727(11) 0.0303 1.0000 Uani .
C23 C -0.08693(11) 0.38173(7) 0.12155(10) 0.0281 1.0000 Uani .
C24 C -0.04485(12) 0.40238(8) 0.06284(11) 0.0319 1.0000 Uani .
C25 C 0.07277(12) 0.36902(8) 0.09947(11) 0.0332 1.0000 Uani .
C26 C 0.15183(12) 0.31385(8) 0.19548(11) 0.0319 1.0000 Uani .
C27 C 0.10779(12) 0.29256(8) 0.25303(11) 0.0352 1.0000 Uani .
C28 C -0.00892(12) 0.32571(8) 0.21702(11) 0.0328 1.0000 Uani .
C30 C 0.28325(12) 0.27663(8) 0.24029(12) 0.0374 1.0000 Uani .
C31 C 0.27149(16) 0.18262(9) 0.23274(16) 0.0502 1.0000 Uani .
C32 C 0.31195(15) 0.30539(10) 0.16404(15) 0.0483 1.0000 Uani .
C33 C 0.40124(14) 0.30287(11) 0.37223(13) 0.0522 1.0000 Uani .
H91 H -0.9028 0.3152 -0.1619 0.0347 1.0000 Uiso R
H101 H -0.9828 0.4575 -0.1772 0.0354 1.0000 Uiso R
H121 H -0.5586 0.1874 0.0954 0.0433 1.0000 Uiso R
H131 H -0.6456 0.0560 0.0674 0.0492 1.0000 Uiso R
H151 H -0.9280 0.0945 -0.3015 0.0404 1.0000 Uiso R
H161 H -0.8394 0.2248 -0.2718 0.0349 1.0000 Uiso R
H181 H -0.8473 -0.1338 -0.2115 0.0826 1.0000 Uiso R
H182 H -0.8439 -0.0525 -0.2699 0.0825 1.0000 Uiso R
H183 H -0.7076 -0.0800 -0.1307 0.0835 1.0000 Uiso R
H192 H -0.8493 -0.1182 -0.0432 0.0890 1.0000 Uiso R
H191 H -0.8355 -0.0278 0.0085 0.0876 1.0000 Uiso R
H193 H -0.7065 -0.0718 0.0386 0.0888 1.0000 Uiso R
H202 H -1.0423 -0.0834 -0.2546 0.0918 1.0000 Uiso R
H201 H -1.0429 0.0062 -0.2081 0.0924 1.0000 Uiso R
H203 H -1.0466 0.0003 -0.3178 0.0916 1.0000 Uiso R
H211 H -0.4607 0.1893 -0.0327 0.0348 1.0000 Uiso R
H221 H -0.2472 0.2468 0.0397 0.0353 1.0000 Uiso R
H241 H -0.0994 0.4396 -0.0060 0.0360 1.0000 Uiso R
H251 H 0.0975 0.3841 0.0545 0.0378 1.0000 Uiso R
H271 H 0.1630 0.2554 0.3243 0.0402 1.0000 Uiso R
H281 H -0.0345 0.3108 0.2621 0.0371 1.0000 Uiso R
H311 H 0.3535 0.1602 0.2562 0.0741 1.0000 Uiso R
H312 H 0.2633 0.1611 0.2883 0.0741 1.0000 Uiso R
H313 H 0.1901 0.1662 0.1443 0.0741 1.0000 Uiso R
H322 H 0.3956 0.2821 0.1943 0.0693 1.0000 Uiso R
H321 H 0.3145 0.3663 0.1598 0.0700 1.0000 Uiso R
H323 H 0.2393 0.2849 0.0806 0.0688 1.0000 Uiso R
H332 H 0.4857 0.2790 0.4044 0.0759 1.0000 Uiso R
H331 H 0.4095 0.3627 0.3785 0.0757 1.0000 Uiso R
H333 H 0.3878 0.2828 0.4262 0.0757 1.0000 Uiso R
H51 H -0.4589(12) 0.4306(8) 0.0091(13) 0.0342(18) 1.0000 Uiso D
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0137 0.0067 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0241 0.0134 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 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
7 3 -2 0.0370
-7 -3 2 0.0460
0 4 1 0.0590
1 -11 -3 0.0540
-5 3 2 0.0350
-7 -3 5 0.0470
5 -2 -2 0.0460
7 3 -5 0.0670
-1 1 3 0.0460
1 -1 -3 0.0470
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 C8 106.07(9) yes
C3 2_465 C2 N1 125.73(10) yes
C3 2_465 C2 C10 124.21(10) yes
N1 . C2 C10 110.06(10) yes
C2 2_465 C3 C4 125.38(10) yes
C2 2_465 C3 C23 117.88(10) yes
C4 . C3 C23 116.74(10) yes
C3 . C4 N5 126.61(10) yes
C3 . C4 C22 126.25(10) yes
N5 . C4 C22 107.15(10) yes
C4 . N5 C6 109.54(9) yes
C4 . N5 H51 124.1(8) no
C6 . N5 H51 126.3(8) no
N5 . C6 C7 126.97(10) yes
N5 . C6 C21 107.35(10) yes
C7 . C6 C21 125.66(11) yes
C6 . C7 C8 124.95(10) yes
C6 . C7 C11 116.73(10) yes
C8 . C7 C11 118.31(10) yes
C7 . C8 N1 125.83(10) yes
C7 . C8 C9 124.18(10) yes
N1 . C8 C9 110.00(10) yes
C8 . C9 C10 106.97(10) yes
C8 . C9 H91 125.5 no
C10 . C9 H91 127.5 no
C2 . C10 C9 106.89(10) yes
C2 . C10 H101 126.1 no
C9 . C10 H101 127.0 no
C7 . C11 C12 120.07(10) yes
C7 . C11 C16 122.36(10) yes
C12 . C11 C16 117.57(11) yes
C11 . C12 C13 121.16(11) yes
C11 . C12 H121 120.1 no
C13 . C12 H121 118.7 no
C12 . C13 C14 121.60(12) yes
C12 . C13 H131 118.3 no
C14 . C13 H131 120.1 no
C13 . C14 C15 116.81(11) yes
C13 . C14 C17 122.71(12) yes
C15 . C14 C17 120.36(11) yes
C14 . C15 C16 121.73(11) yes
C14 . C15 H151 120.2 no
C16 . C15 H151 118.1 no
C11 . C16 C15 121.09(11) yes
C11 . C16 H161 119.4 no
C15 . C16 H161 119.5 no
C14 . C17 C18 107.74(12) yes
C14 . C17 C19 111.95(12) yes
C18 . C17 C19 109.40(13) yes
C14 . C17 C20 111.10(12) yes
C18 . C17 C20 109.05(14) yes
C19 . C17 C20 107.57(14) yes
C17 . C18 H181 110.0 no
C17 . C18 H182 108.1 no
H181 . C18 H182 106.4 no
C17 . C18 H183 110.3 no
H181 . C18 H183 111.6 no
H182 . C18 H183 110.3 no
C17 . C19 H192 111.7 no
C17 . C19 H191 110.3 no
H192 . C19 H191 106.4 no
C17 . C19 H193 113.8 no
H192 . C19 H193 107.6 no
H191 . C19 H193 106.7 no
C17 . C20 H202 107.2 no
C17 . C20 H201 109.6 no
H202 . C20 H201 112.2 no
C17 . C20 H203 109.0 no
H202 . C20 H203 108.2 no
H201 . C20 H203 110.5 no
C6 . C21 C22 107.80(10) yes
C6 . C21 H211 125.8 no
C22 . C21 H211 126.4 no
C4 . C22 C21 108.15(10) yes
C4 . C22 H221 125.3 no
C21 . C22 H221 126.5 no
C3 . C23 C24 121.59(10) yes
C3 . C23 C28 120.46(10) yes
C24 . C23 C28 117.95(10) yes
C23 . C24 C25 121.07(11) yes
C23 . C24 H241 119.5 no
C25 . C24 H241 119.4 no
C24 . C25 C26 121.27(11) yes
C24 . C25 H251 118.4 no
C26 . C25 H251 120.3 no
C25 . C26 C27 117.29(11) yes
C25 . C26 C30 123.09(11) yes
C27 . C26 C30 119.61(11) yes
C26 . C27 C28 121.59(11) yes
C26 . C27 H271 120.2 no
C28 . C27 H271 118.1 no
C23 . C28 C27 120.82(11) yes
C23 . C28 H281 120.1 no
C27 . C28 H281 119.1 no
C26 . C30 C31 109.28(11) yes
C26 . C30 C32 111.76(11) yes
C31 . C30 C32 108.46(12) yes
C26 . C30 C33 108.93(11) yes
C31 . C30 C33 109.70(12) yes
C32 . C30 C33 108.70(12) yes
C30 . C31 H311 108.1 no
C30 . C31 H312 110.9 no
H311 . C31 H312 109.1 no
C30 . C31 H313 108.7 no
H311 . C31 H313 108.3 no
H312 . C31 H313 111.7 no
C30 . C32 H322 110.6 no
C30 . C32 H321 113.1 no
H322 . C32 H321 109.8 no
C30 . C32 H323 108.5 no
H322 . C32 H323 107.0 no
H321 . C32 H323 107.6 no
C30 . C33 H332 111.2 no
C30 . C33 H331 110.6 no
H332 . C33 H331 109.4 no
C30 . C33 H333 111.0 no
H332 . C33 H333 105.9 no
H331 . C33 H333 108.6 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.3711(14) yes
N1 C8 . 1.3705(14) yes
C2 C3 2_465 1.4051(16) yes
C2 C10 . 1.4485(16) yes
C3 C4 . 1.4003(16) yes
C3 C23 . 1.4959(15) yes
C4 N5 . 1.3719(14) yes
C4 C22 . 1.4313(16) yes
N5 C6 . 1.3700(15) yes
N5 H51 . 0.854(12) no
C6 C7 . 1.4005(16) yes
C6 C21 . 1.4327(15) yes
C7 C8 . 1.4033(15) yes
C7 C11 . 1.4960(15) yes
C8 C9 . 1.4491(15) yes
C9 C10 . 1.3466(17) yes
C9 H91 . 0.954 no
C10 H101 . 0.952 no
C11 C12 . 1.3912(17) yes
C11 C16 . 1.3911(16) yes
C12 C13 . 1.3876(18) yes
C12 H121 . 0.989 no
C13 C14 . 1.3943(18) yes
C13 H131 . 1.001 no
C14 C15 . 1.3948(17) yes
C14 C17 . 1.5343(17) yes
C15 C16 . 1.3864(17) yes
C15 H151 . 0.976 no
C16 H161 . 0.974 no
C17 C18 . 1.524(2) yes
C17 C19 . 1.531(2) yes
C17 C20 . 1.545(2) yes
C18 H181 . 0.990 no
C18 H182 . 1.020 no
C18 H183 . 0.990 no
C19 H192 . 0.979 no
C19 H191 . 1.040 no
C19 H193 . 1.010 no
C20 H202 . 0.998 no
C20 H201 . 0.957 no
C20 H203 . 1.031 no
C21 C22 . 1.3559(17) yes
C21 H211 . 0.949 no
C22 H221 . 0.942 no
C23 C24 . 1.3926(17) yes
C23 C28 . 1.3944(16) yes
C24 C25 . 1.3948(16) yes
C24 H241 . 0.972 no
C25 C26 . 1.3905(17) yes
C25 H251 . 0.979 no
C26 C27 . 1.4016(18) yes
C26 C30 . 1.5361(16) yes
C27 C28 . 1.3864(16) yes
C27 H271 . 0.993 no
C28 H281 . 0.988 no
C30 C31 . 1.535(2) yes
C30 C32 . 1.528(2) yes
C30 C33 . 1.5341(19) yes
C31 H311 . 0.980 no
C31 H312 . 0.989 no
C31 H313 . 1.028 no
C32 H322 . 0.967 no
C32 H321 . 0.996 no
C32 H323 . 0.986 no
C33 H332 . 0.970 no
C33 H331 . 0.977 no
C33 H333 . 1.008 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N5 H51 N1 2_465 122.2(10) 0.854 2.373 2.919(2) yes
