#------------------------------------------------------------------------------
#$Date: 2020-04-16 23:53:15 +0300 (Thu, 16 Apr 2020) $
#$Revision: 250858 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/47/4134736.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_4134736
loop_
_publ_author_name
'Gonzalez-Rodriguez, Edgar'
'Abdo, Miguel A.'
'Dos Passos Gomes, Gabriel'
'Ayad, Suliman'
'White, Frankie D.'
'Tsvetkov, Nikolay P.'
'Hanson, Kenneth'
'Alabugin, Igor V.'
_publ_section_title
;
 Twofold π-Extension of Polyarenes via Double and Triple Radical Alkyne
 peri-Annulations: Radical Cascades Converging on the Same Aromatic
 Core.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c01856
_journal_year                    2020
_chemical_formula_moiety         'C56 H68 Sn2'
_chemical_formula_sum            'C56 H68 Sn2'
_chemical_formula_weight         978.52
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-02-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90.7726(14)
_cell_angle_beta                 102.0131(14)
_cell_angle_gamma                114.0745(13)
_cell_formula_units_Z            1
_cell_length_a                   10.0922(6)
_cell_length_b                   11.2174(6)
_cell_length_c                   12.9069(7)
_cell_measurement_reflns_used    4584
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.442
_cell_measurement_theta_min      2.273
_cell_volume                     1296.91(13)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298.01
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20016
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.546
_diffrn_reflns_theta_min         2.273
_exptl_absorpt_coefficient_mu    0.995
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.1252 before and 0.0425 after correction.
The Ratio of minimum to maximum transmission is 0.8892.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular blocks'
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.786
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         5958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.1558
_refine_ls_R_factor_gt           0.0646
_refine_ls_shift/su_max          0.083
_refine_ls_shift/su_mean         0.020
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1881
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2664
_reflns_number_total             5958
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            2f'_double_periannulations.cif
_cod_data_source_block           july5_nik1_fract2_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'n/a' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4134736
_shelx_shelxl_version_number     2014/7
_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   21.445
_shelx_estimated_absorpt_t_min   2.274
_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
2.a Secondary CH2 refined with riding coordinates:
 C1C(H14a,H14b), C5C(H16a,H16b), C8C(H17a,H17b), C9C(H19a,H19b), C10C(H20a,
 H20b), C2C(H3a,H3b), C11C(H8a,H8b)
2.b Aromatic/amide H refined with riding coordinates:
 C26C(H5AA), C16C(H6AA), C22C(H10), C18C(H11), C28C(H1AA), C17C(H13),
 C23C(H15), C20C(H18), C19C(H0AA), C3C(H5), C6C(H6)
2.c Idealised Me refined as rotating group:
 C4C(H7a,H7b,H7c), C7C(H9a,H9b,H9c), C12C(H12a,H12b,H12c)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Sn1 Sn 0.90847(5) 0.51359(5) 0.23833(3) 0.1074(3) Uani 1 1 d . . . . .
C1 C 0.5478(7) 0.6228(5) 0.4562(4) 0.0853(15) Uani 1 1 d . . . . .
C2 C 0.5570(6) 0.4069(5) 0.4791(4) 0.0789(14) Uani 1 1 d . . . . .
C2AA C 0.6147(7) 0.3142(5) 0.4578(5) 0.0896(16) Uani 1 1 d . . . . .
C4 C 0.7799(8) 0.2472(6) 0.3729(6) 0.0999(18) Uani 1 1 d . . . . .
C3AA C 0.6052(6) 0.5269(5) 0.4341(4) 0.0786(14) Uani 1 1 d . . . . .
C4AA C 0.7184(6) 0.3435(5) 0.3919(4) 0.0856(15) Uani 1 1 d . . . . .
C5AA C 0.7031(6) 0.5497(5) 0.3708(4) 0.0875(15) Uani 1 1 d . . . . .
H5AA H 0.7341 0.6293 0.3419 0.105 Uiso 1 1 calc R . . . .
C6AA C 0.7177(10) 0.1586(7) 0.2842(6) 0.126(2) Uani 1 1 d . . . . .
H6AA H 0.6349 0.1567 0.2351 0.151 Uiso 1 1 calc R . . . .
C7AA C 0.7610(6) 0.4596(6) 0.3459(4) 0.0852(14) Uani 1 1 d . . . . .
C10 C 0.5657(9) 0.1956(6) 0.5034(6) 0.118(2) Uani 1 1 d . . . . .
H10 H 0.6032 0.1348 0.4913 0.141 Uiso 1 1 calc R . . . .
C11 C 0.8930(16) 0.0687(11) 0.3376(13) 0.171(5) Uani 1 1 d . . . . .
H11 H 0.9293 0.0066 0.3270 0.205 Uiso 1 1 calc R . . . .
C1AA C 0.5925(8) 0.7422(6) 0.4155(6) 0.115(2) Uani 1 1 d . . . . .
H1AA H 0.6623 0.7636 0.3739 0.137 Uiso 1 1 calc R . . . .
C13 C 0.7801(15) 0.0693(9) 0.2669(10) 0.159(4) Uani 1 1 d . . . . .
H13 H 0.7403 0.0109 0.2051 0.190 Uiso 1 1 calc R . . . .
C14 C 1.1082(8) 0.4884(8) 0.2916(8) 0.145(3) Uani 1 1 d . . . . .
H14A H 1.1930 0.5730 0.3004 0.175 Uiso 1 1 calc R . . . .
H14B H 1.1090 0.4552 0.3607 0.175 Uiso 1 1 calc R . . . .
C15 C 0.4659(9) 0.1676(7) 0.5640(7) 0.141(3) Uani 1 1 d . . . . .
H15 H 0.4351 0.0879 0.5928 0.169 Uiso 1 1 calc R . . . .
C16 C 0.7879(11) 0.3997(10) 0.0867(6) 0.156(3) Uani 1 1 d . . . . .
H16A H 0.8405 0.4421 0.0332 0.187 Uiso 1 1 calc R . . . .
H16B H 0.7899 0.3140 0.0898 0.187 Uiso 1 1 calc R . . . .
C17 C 0.6366(13) 0.3808(12) 0.0523(8) 0.188(4) Uani 1 1 d . . . . .
H17A H 0.6337 0.4647 0.0394 0.226 Uiso 1 1 calc R . . . .
H17B H 0.5853 0.3473 0.1085 0.226 Uiso 1 1 calc R . . . .
C18 C 0.8993(11) 0.2459(8) 0.4438(8) 0.149(3) Uani 1 1 d . . . . .
H18 H 0.9413 0.3056 0.5048 0.179 Uiso 1 1 calc R . . . .
C19 C 0.9653(12) 0.7134(10) 0.2269(9) 0.176(4) Uani 1 1 d . . . . .
H19A H 0.8757 0.7252 0.1963 0.211 Uiso 1 1 calc R . . . .
H19B H 1.0066 0.7606 0.2979 0.211 Uiso 1 1 calc R . . . .
C20 C 1.0784(19) 0.7720(13) 0.1588(13) 0.261(8) Uani 1 1 d . . . . .
H20A H 1.1612 0.7489 0.1848 0.314 Uiso 1 1 calc R . . . .
H20B H 1.0315 0.7293 0.0866 0.314 Uiso 1 1 calc R . . . .
C3 C 1.1243(10) 0.3954(10) 0.2158(9) 0.167(3) Uani 1 1 d . . . . .
H3A H 1.0381 0.3116 0.2063 0.201 Uiso 1 1 calc R . . . .
H3B H 1.1237 0.4294 0.1470 0.201 Uiso 1 1 calc R . . . .
C0AA C 0.9603(13) 0.1591(12) 0.4285(11) 0.182(4) Uani 1 1 d . . . . .
H0AA H 1.0434 0.1608 0.4771 0.219 Uiso 1 1 calc R . . . .
C5 C 1.2571(13) 0.3736(14) 0.2487(13) 0.216(5) Uani 1 1 d . . . . .
H5 H 1.3308 0.4185 0.3096 0.259 Uiso 1 1 calc R . . . .
C6 C 0.5500(18) 0.279(2) -0.0555(14) 0.300(12) Uani 1 1 d . . . . .
H6 H 0.5909 0.2294 -0.0840 0.360 Uiso 1 1 calc R . . . .
C7 C 1.2667(15) 0.2794(15) 0.1819(13) 0.263(7) Uani 1 1 d . . . . .
H7A H 1.1699 0.2268 0.1372 0.394 Uiso 1 1 calc GR . . . .
H7B H 1.3022 0.2241 0.2244 0.394 Uiso 1 1 calc GR . . . .
H7C H 1.3348 0.3227 0.1382 0.394 Uiso 1 1 calc GR . . . .
C8 C 1.137(3) 0.9076(18) 0.154(2) 0.413(18) Uani 1 1 d . . . . .
H8A H 1.2122 0.9521 0.2188 0.496 Uiso 1 1 calc R . . . .
H8B H 1.0583 0.9374 0.1481 0.496 Uiso 1 1 calc R . . . .
C9 C 0.434(3) 0.274(2) -0.0936(18) 0.353(14) Uani 1 1 d . . . . .
H9A H 0.3683 0.1861 -0.1253 0.530 Uiso 1 1 calc GR . . . .
H9B H 0.4418 0.3332 -0.1475 0.530 Uiso 1 1 calc GR . . . .
H9C H 0.3937 0.2987 -0.0398 0.530 Uiso 1 1 calc GR . . . .
C12 C 1.209(3) 0.9429(17) 0.055(2) 0.49(2) Uani 1 1 d . . . . .
H12A H 1.1349 0.8973 -0.0088 0.734 Uiso 1 1 calc GR . . . .
H12B H 1.2897 0.9169 0.0628 0.734 Uiso 1 1 calc GR . . . .
H12C H 1.2459 1.0359 0.0514 0.734 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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
C14 Sn1 C7AA 114.6(3) . . ?
C14 Sn1 C16 109.6(3) . . ?
C16 Sn1 C7AA 108.3(3) . . ?
C19 Sn1 C7AA 105.0(3) . . ?
C19 Sn1 C14 108.4(4) . . ?
C19 Sn1 C16 111.0(4) . . ?
C2 C1 C3AA 119.8(5) 2_666 . ?
C1AA C1 C2 118.5(5) . 2_666 ?
C1AA C1 C3AA 121.7(5) . . ?
C1 C2 C2AA 120.2(5) 2_666 . ?
C3AA C2 C1 121.0(5) . 2_666 ?
C3AA C2 C2AA 118.9(5) . . ?
C4AA C2AA C2 120.1(5) . . ?
C10 C2AA C2 118.0(5) . . ?
C10 C2AA C4AA 121.9(5) . . ?
C6AA C4 C4AA 120.7(7) . . ?
C6AA C4 C18 118.6(7) . . ?
C18 C4 C4AA 120.7(6) . . ?
C2 C3AA C1 119.3(4) . . ?
C5AA C3AA C1 121.9(5) . . ?
C5AA C3AA C2 118.9(5) . . ?
C2AA C4AA C4 119.2(5) . . ?
C7AA C4AA C2AA 120.4(5) . . ?
C7AA C4AA C4 120.4(5) . . ?
C3AA C5AA C7AA 124.2(5) . . ?
C4 C6AA C13 119.6(9) . . ?
C4AA C7AA Sn1 124.7(4) . . ?
C4AA C7AA C5AA 117.6(5) . . ?
C5AA C7AA Sn1 117.7(4) . . ?
C15 C10 C2AA 121.6(6) . . ?
C13 C11 C0AA 121.4(10) . . ?
C1 C1AA C15 121.0(6) . 2_666 ?
C11 C13 C6AA 120.2(11) . . ?
C3 C14 Sn1 112.5(6) . . ?
C10 C15 C1AA 120.7(6) . 2_666 ?
C17 C16 Sn1 116.2(7) . . ?
C16 C17 C6 112.2(10) . . ?
C4 C18 C0AA 122.4(9) . . ?
C20 C19 Sn1 112.6(8) . . ?
C8 C20 C19 118.1(13) . . ?
C5 C3 C14 114.8(9) . . ?
C18 C0AA C11 117.6(11) . . ?
C7 C5 C3 114.8(12) . . ?
C9 C6 C17 114.4(19) . . ?
C20 C8 C12 110.2(17) . . ?
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
Sn1 C7AA 2.157(5) . ?
Sn1 C14 2.123(7) . ?
Sn1 C16 2.149(8) . ?
Sn1 C19 2.091(10) . ?
C1 C2 1.419(7) 2_666 ?
C1 C3AA 1.464(7) . ?
C1 C1AA 1.378(8) . ?
C2 C1 1.419(7) 2_666 ?
C2 C2AA 1.431(7) . ?
C2 C3AA 1.411(7) . ?
C2AA C4AA 1.423(8) . ?
C2AA C10 1.402(8) . ?
C4 C4AA 1.488(8) . ?
C4 C6AA 1.362(10) . ?
C4 C18 1.357(10) . ?
C3AA C5AA 1.358(7) . ?
C4AA C7AA 1.381(8) . ?
C5AA C7AA 1.421(7) . ?
C6AA C13 1.420(12) . ?
C10 C15 1.342(9) . ?
C11 C13 1.305(14) . ?
C11 C0AA 1.393(16) . ?
C1AA C15 1.409(8) 2_666 ?
C14 C3 1.500(11) . ?
C15 C1AA 1.409(8) 2_666 ?
C16 C17 1.423(13) . ?
C17 C6 1.623(18) . ?
C18 C0AA 1.379(12) . ?
C19 C20 1.527(14) . ?
C20 C8 1.397(18) . ?
C3 C5 1.439(13) . ?
C5 C7 1.402(15) . ?
C6 C9 1.15(2) . ?
C8 C12 1.57(2) . ?
