#------------------------------------------------------------------------------
#$Date: 2019-11-02 07:01:25 +0200 (Sat, 02 Nov 2019) $
#$Revision: 220884 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/76/4127687.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_4127687
loop_
_publ_author_name
'Li, Zhengtao'
'Gopalakrishna, Tullimilli Y.'
'Han, Yi'
'Gu, Yanwei'
'Yuan, Liu'
'Zeng, Wangdong'
'Casanova, David'
'Wu, Jishan'
_publ_section_title
;
 [6]Cyclo-para-phenylmethine: An Analog of Benzene Showing Global
 Aromaticity and Open-Shell Diradical Character.
;
_journal_issue                   41
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16266
_journal_page_last               16270
_journal_paper_doi               10.1021/jacs.9b09780
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C96 H90 [+ solvent]'
_chemical_formula_sum            'C48 H45'
_chemical_formula_weight         621.84
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90.369(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.435(2)
_cell_length_b                   26.395(3)
_cell_length_c                   10.1346(11)
_cell_measurement_reflns_used    9795
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.39
_cell_measurement_theta_min      2.82
_cell_volume                     5198.8(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0810
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            37026
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.428
_diffrn_reflns_theta_min         2.823
_exptl_absorpt_coefficient_mu    0.334
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    0.794
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1332
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         5142
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0941
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1673P)²+6.1294P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2690
_refine_ls_wR_factor_ref         0.2811
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4412
_reflns_number_total             5142
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b09780_si_002.cif
_cod_data_source_block           Neutral
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-Scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4127687
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
C1 C 0.500000 0.28191(9) 0.000000 0.0272(5) Uani 1 2 d S T P
C2 C 0.53895(10) 0.30802(7) 0.09838(18) 0.0304(4) Uani 1 1 d . . .
C3 C 0.5563(2) 0.28570(9) 0.2202(3) 0.0751(11) Uani 1 1 d . . .
H3 H 0.544786 0.251188 0.234919 0.090 Uiso 1 1 calc R U .
C4 C 0.5892(2) 0.31219(9) 0.3185(3) 0.0774(12) Uani 1 1 d . . .
H4 H 0.597977 0.295759 0.400312 0.093 Uiso 1 1 calc R U .
C5 C 0.61057(10) 0.36282(7) 0.30267(18) 0.0303(4) Uani 1 1 d . . .
C6 C 0.59958(15) 0.38293(9) 0.1757(2) 0.0505(7) Uani 1 1 d . . .
H6 H 0.616605 0.415843 0.156627 0.061 Uiso 1 1 calc R U .
C7 C 0.56560(15) 0.35713(9) 0.07932(19) 0.0488(7) Uani 1 1 d . . .
H7 H 0.559546 0.372828 -0.004314 0.059 Uiso 1 1 calc R U .
C8 C 0.64129(10) 0.39127(7) 0.40695(19) 0.0322(5) Uani 1 1 d . . .
C9 C 0.64000(10) 0.44529(7) 0.40945(17) 0.0301(4) Uani 1 1 d . . .
C10 C 0.58771(12) 0.47418(7) 0.3491(2) 0.0391(5) Uani 1 1 d . . .
H10 H 0.550837 0.456954 0.306509 0.047 Uiso 1 1 calc R U .
C11 C 0.68818(18) 0.47422(10) 0.4805(5) 0.0891(14) Uani 1 1 d . U .
H11 H 0.722347 0.457032 0.530794 0.107 Uiso 1 1 calc R U .
C12 C 0.500000 0.22555(9) 0.000000 0.0305(6) Uani 1 2 d S T P
C13 C 0.44542(13) 0.19907(8) 0.0585(2) 0.0433(6) Uani 1 1 d . . .
C14 C 0.38757(13) 0.22710(11) 0.1227(2) 0.0505(6) Uani 1 1 d . . .
H14A H 0.352500 0.202915 0.151559 0.076 Uiso 1 1 calc R U .
H14B H 0.367162 0.250866 0.059283 0.076 Uiso 1 1 calc R U .
H14C H 0.405208 0.245863 0.199188 0.076 Uiso 1 1 calc R U .
C15 C 0.44676(17) 0.14637(10) 0.0564(3) 0.0682(9) Uani 1 1 d . . .
H15 H 0.409808 0.128206 0.094972 0.082 Uiso 1 1 calc R U .
C16 C 0.500000 0.11966(14) 0.000000 0.0852(16) Uani 1 2 d S T P
C17 C 0.500000 0.06183(17) 0.000000 0.150(4) Uani 1 2 d S TU P
H17A H 0.547094 0.049459 0.013061 0.225 Uiso 0.5 1 calc R U P
H17B H 0.482089 0.049459 -0.084672 0.225 Uiso 0.5 1 calc R U P
H17C H 0.470817 0.049459 0.071611 0.225 Uiso 0.5 1 calc R U P
C18 C 0.67514(11) 0.36426(7) 0.5195(2) 0.0349(5) Uani 1 1 d . . .
C19 C 0.73639(14) 0.33729(9) 0.5022(2) 0.0477(6) Uani 1 1 d . . .
C20 C 0.76893(18) 0.33265(14) 0.3695(3) 0.0698(9) Uani 1 1 d . . .
H20A H 0.814206 0.316658 0.378870 0.105 Uiso 1 1 calc R U .
H20B H 0.774250 0.366405 0.330660 0.105 Uiso 1 1 calc R U .
H20C H 0.739663 0.311827 0.312047 0.105 Uiso 1 1 calc R U .
C21 C 0.76810(16) 0.31548(11) 0.6118(3) 0.0594(7) Uani 1 1 d . . .
H21 H 0.809304 0.296748 0.599427 0.071 Uiso 1 1 calc R U .
C22 C 0.74239(15) 0.31990(10) 0.7364(3) 0.0546(7) Uani 1 1 d . . .
C23 C 0.7803(2) 0.29827(14) 0.8550(3) 0.0776(10) Uani 1 1 d . . .
H23A H 0.786933 0.261777 0.842798 0.116 Uiso 1 1 calc R U .
H23B H 0.753200 0.304200 0.934807 0.116 Uiso 1 1 calc R U .
H23C H 0.825155 0.314879 0.864131 0.116 Uiso 1 1 calc R U .
C24 C 0.68040(14) 0.34483(10) 0.7515(2) 0.0502(6) Uani 1 1 d . . .
H24 H 0.660747 0.346895 0.836900 0.060 Uiso 1 1 calc R U .
C25 C 0.64582(12) 0.36703(8) 0.6454(2) 0.0416(5) Uani 1 1 d . . .
C26 C 0.57836(14) 0.39366(13) 0.6687(3) 0.0633(8) Uani 1 1 d . . .
H26A H 0.561690 0.385494 0.757210 0.095 Uiso 1 1 calc R U .
H26B H 0.544514 0.382460 0.602765 0.095 Uiso 1 1 calc R U .
H26C H 0.585009 0.430350 0.661129 0.095 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 0.0181 0.0091 '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
C2 C1 C2 122.2(2) 2_655 .
C2 C1 C12 118.90(11) 2_655 .
C2 C1 C12 118.91(11) . .
C3 C2 C7 114.78(18) . .
C3 C2 C1 122.31(17) . .
C7 C2 C1 122.86(17) . .
C4 C3 C2 122.1(2) . .
C4 C3 H3 118.9 . .
C2 C3 H3 118.9 . .
C3 C4 C5 122.5(2) . .
C3 C4 H4 118.8 . .
C5 C4 H4 118.8 . .
C6 C5 C4 114.77(18) . .
C6 C5 C8 122.69(17) . .
C4 C5 C8 122.54(18) . .
C7 C6 C5 122.60(19) . .
C7 C6 H6 118.7 . .
C5 C6 H6 118.7 . .
C6 C7 C2 122.65(19) . .
C6 C7 H7 118.7 . .
C2 C7 H7 118.7 . .
C5 C8 C9 122.20(16) . .
C5 C8 C18 119.69(16) . .
C9 C8 C18 118.10(16) . .
C11 C9 C10 113.95(19) . .
C11 C9 C8 122.77(18) . .
C10 C9 C8 123.13(18) . .
C10 C10 C9 122.81(11) 6_565 .
C10 C10 H10 118.6 6_565 .
C9 C10 H10 118.6 . .
C11 C11 C9 122.96(13) 6_565 .
C11 C11 H11 118.5 6_565 .
C9 C11 H11 118.5 . .
C13 C12 C13 120.3(3) . 2_655
C13 C12 C1 119.83(13) . .
C13 C12 C1 119.83(13) 2_655 .
C15 C13 C12 118.4(3) . .
C15 C13 C14 121.0(2) . .
C12 C13 C14 120.6(2) . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C16 C15 C13 122.1(3) . .
C16 C15 H15 118.9 . .
C13 C15 H15 118.9 . .
C15 C16 C15 118.5(3) . 2_655
C15 C16 C17 120.75(17) . .
C15 C16 C17 120.75(17) 2_655 .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C16 C17 H17A 109.472(14) . 2_655
H17A C17 H17A 141.1 . 2_655
H17B C17 H17A 56.2 . 2_655
H17C C17 H17A 56.3 . 2_655
C16 C17 H17B 109.470(13) . 2_655
H17A C17 H17B 56.3 . 2_655
H17B C17 H17B 141.1 . 2_655
H17C C17 H17B 56.3 . 2_655
H17A C17 H17B 109.5 2_655 2_655
C16 C17 H17C 109.471(3) . 2_655
H17A C17 H17C 56.3 . 2_655
H17B C17 H17C 56.2 . 2_655
H17C C17 H17C 141.1 . 2_655
H17A C17 H17C 109.5 2_655 2_655
H17B C17 H17C 109.5 2_655 2_655
C19 C18 C25 119.45(19) . .
C19 C18 C8 121.2(2) . .
C25 C18 C8 119.36(19) . .
C21 C19 C18 118.9(2) . .
C21 C19 C20 119.8(2) . .
C18 C19 C20 121.3(2) . .
C19 C20 H20A 109.5 . .
C19 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C19 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C22 C21 C19 122.7(3) . .
C22 C21 H21 118.7 . .
C19 C21 H21 118.7 . .
C21 C22 C24 117.9(2) . .
C21 C22 C23 121.5(3) . .
C24 C22 C23 120.7(3) . .
C22 C23 H23A 109.5 . .
C22 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C22 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C22 C24 C25 122.1(2) . .
C22 C24 H24 119.0 . .
C25 C24 H24 119.0 . .
C24 C25 C18 118.9(2) . .
C24 C25 C26 119.4(2) . .
C18 C25 C26 121.68(19) . .
C25 C26 H26A 109.5 . .
C25 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C25 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.426(2) 2_655
C1 C2 1.426(2) .
C1 C12 1.488(3) .
C2 C3 1.407(3) .
C2 C7 1.410(3) .
C3 C4 1.372(3) .
C3 H3 0.9500 .
C4 C5 1.409(3) .
C4 H4 0.9500 .
C5 C6 1.407(3) .
C5 C8 1.424(3) .
C6 C7 1.359(3) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C8 C9 1.427(3) .
C8 C18 1.494(2) .
C9 C11 1.403(3) .
C9 C10 1.407(3) .
C10 C10 1.363(4) 6_565
C10 H10 0.9500 .
C11 C11 1.361(5) 6_565
C11 H11 0.9500 .
C12 C13 1.405(3) .
C12 C13 1.405(3) 2_655
C13 C15 1.391(3) .
C13 C14 1.498(4) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 C16 1.379(4) .
C15 H15 0.9500 .
C16 C17 1.526(5) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C17 H17A 0.9800 2_655
C17 H17B 0.9800(15) 2_655
C17 H17C 0.9800 2_655
C18 C19 1.399(3) .
C18 C25 1.403(3) .
C19 C21 1.392(3) .
C19 C20 1.494(4) .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 C22 1.366(4) .
C21 H21 0.9500 .
C22 C24 1.382(4) .
C22 C23 1.517(3) .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C24 C25 1.393(3) .
C24 H24 0.9500 .
C25 C26 1.508(4) .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
