#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/18/7121882.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_7121882
loop_
_publ_author_name
'Spisak, Sarah N.'
'Wei, Zheng'
'Darzi, Evan'
'Jasti, Ramesh'
'Petrukhina, Marina A.'
_publ_section_title
;
 Highly strained [6]cycloparaphenylene: crystallization of an unsolvated
 polymorph and the first mono- and dianions.
;
_journal_issue                   56
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7818
_journal_page_last               7821
_journal_paper_doi               10.1039/c8cc03693d
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C36 H24'
_chemical_formula_sum            'C36 H24'
_chemical_formula_weight         456.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2018-05-02 deposited with the CCDC.
2018-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.3290(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.1772(5)
_cell_length_b                   10.3120(4)
_cell_length_c                   11.2725(5)
_cell_measurement_reflns_used    8255
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.09
_cell_measurement_theta_min      4.12
_cell_volume                     1246.85(9)
_computing_cell_refinement       'SAINT V.8.37A (Bruker AXS Inc., 2016)'
_computing_data_collection       'APEX3 v.2016.9-0 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V.8.37A (Bruker AXS Inc., 2016)'
_computing_molecular_graphics    'Xshell v.6.3.1 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v.2016.9-0 (Bruker AXS Inc., 2016)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_source         'INCOATEC ImuS micro-focus source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10681
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.086
_diffrn_reflns_theta_min         4.121
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was 
used for absorption correction. 
Krause, L., Herbst-Irmer, R., 
Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.160
_exptl_transmission_factor_max   1
_exptl_transmission_factor_min   0.9326
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2409
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0414
_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/[σ²(Fo²)+(0.0512P)²+0.7401P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1076
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2278
_reflns_number_total             2409
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc03693d2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_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 

 Adding full bibliography for 7121882--7121884.cif.
;
_cod_database_code               7121882
_shelx_shelxl_version_number     2017/1
_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_min   0.894
_shelx_estimated_absorpt_t_max   0.921
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.82755(12) 0.22006(13) 0.64322(12) 0.0202(3) Uani 1 1 d . .
H1 H 0.831695 0.134097 0.614336 0.024 Uiso 1 1 calc R U
C2 C 0.88990(11) 0.31854(13) 0.60200(12) 0.0197(3) Uani 1 1 d . .
H2 H 0.935977 0.299527 0.545013 0.024 Uiso 1 1 calc R U
C3 C 0.88565(11) 0.44683(13) 0.64383(11) 0.0190(3) Uani 1 1 d . .
C4 C 0.84294(12) 0.46316(13) 0.74870(12) 0.0212(3) Uani 1 1 d . .
H4 H 0.857514 0.542913 0.792603 0.025 Uiso 1 1 calc R U
C5 C 0.77976(12) 0.36442(13) 0.78907(12) 0.0214(3) Uani 1 1 d . .
H5 H 0.750826 0.377892 0.859692 0.026 Uiso 1 1 calc R U
C6 C 0.75799(12) 0.24526(13) 0.72736(11) 0.0196(3) Uani 1 1 d . .
C7 C 0.83144(11) 0.54174(13) 0.43433(12) 0.0188(3) Uani 1 1 d . .
H7 H 0.843518 0.460821 0.399091 0.023 Uiso 1 1 calc R U
C8 C 0.76528(12) 0.63872(12) 0.35888(12) 0.0191(3) Uani 1 1 d . .
H8 H 0.732033 0.623108 0.272814 0.023 Uiso 1 1 calc R U
C9 C 0.74666(12) 0.75957(13) 0.40767(12) 0.0192(3) Uani 1 1 d . .
C10 C 0.82053(12) 0.78682(13) 0.52828(12) 0.0210(3) Uani 1 1 d . .
H10 H 0.825708 0.873382 0.558141 0.025 Uiso 1 1 calc R U
C11 C 0.88587(11) 0.68973(13) 0.60431(12) 0.0203(3) Uani 1 1 d . .
H11 H 0.934439 0.710293 0.685772 0.024 Uiso 1 1 calc R U
C12 C 0.88098(11) 0.56103(12) 0.56206(12) 0.0183(3) Uani 1 1 d . .
C13 C 0.62550(12) 0.82587(12) 0.35134(12) 0.0196(3) Uani 1 1 d . .
C14 C 0.55711(13) 0.81238(13) 0.22646(12) 0.0216(3) Uani 1 1 d . .
H14 H 0.599987 0.804340 0.165035 0.026 Uiso 1 1 calc R U
C15 C 0.42773(13) 0.81067(13) 0.19199(12) 0.0215(3) Uani 1 1 d . .
H15 H 0.383058 0.801357 0.107270 0.026 Uiso 1 1 calc R U
C16 C 0.36198(12) 0.82258(12) 0.28120(12) 0.0199(3) Uani 1 1 d . .
C17 C 0.43000(12) 0.86564(12) 0.39811(12) 0.0200(3) Uani 1 1 d . .
H17 H 0.387038 0.894378 0.454987 0.024 Uiso 1 1 calc R U
C18 C 0.55927(12) 0.86715(12) 0.43258(12) 0.0202(3) Uani 1 1 d . .
H18 H 0.603459 0.896733 0.512733 0.024 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_3
C2 C1 C6 121.05(12) .
C2 C1 H1 119.5 .
C6 C1 H1 119.5 .
C1 C2 C3 120.59(12) .
C1 C2 H2 119.7 .
C3 C2 H2 119.7 .
C4 C3 C2 116.46(12) .
C4 C3 C12 117.77(11) .
C2 C3 C12 122.30(11) .
C5 C4 C3 120.88(12) .
C5 C4 H4 119.6 .
C3 C4 H4 119.6 .
C4 C5 C6 121.01(12) .
C4 C5 H5 119.5 .
C6 C5 H5 119.5 .
C5 C6 C1 116.41(12) .
C5 C6 C16 118.14(11) 3_666
C1 C6 C16 121.74(12) 3_666
C8 C7 C12 121.08(12) .
C8 C7 H7 119.5 .
C12 C7 H7 119.5 .
C7 C8 C9 120.93(12) .
C7 C8 H8 119.5 .
C9 C8 H8 119.5 .
C8 C9 C10 116.46(12) .
C8 C9 C13 117.28(11) .
C10 C9 C13 122.43(12) .
C11 C10 C9 121.19(12) .
C11 C10 H10 119.4 .
C9 C10 H10 119.4 .
C10 C11 C12 120.61(12) .
C10 C11 H11 119.7 .
C12 C11 H11 119.7 .
C7 C12 C11 116.60(12) .
C7 C12 C3 117.29(11) .
C11 C12 C3 123.11(11) .
C18 C13 C14 116.57(12) .
C18 C13 C9 116.51(11) .
C14 C13 C9 123.62(12) .
C15 C14 C13 120.76(12) .
C15 C14 H14 119.6 .
C13 C14 H14 119.6 .
C14 C15 C16 120.73(12) .
C14 C15 H15 119.6 .
C16 C15 H15 119.6 .
C17 C16 C15 116.55(12) .
C17 C16 C6 116.84(11) 3_666
C15 C16 C6 123.60(12) 3_666
C18 C17 C16 121.07(12) .
C18 C17 H17 119.5 .
C16 C17 H17 119.5 .
C17 C18 C13 121.04(12) .
C17 C18 H18 119.5 .
C13 C18 H18 119.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3838(19) .
C1 C6 1.4094(18) .
C1 H1 0.9500 .
C2 C3 1.4097(18) .
C2 H2 0.9500 .
C3 C4 1.4040(18) .
C3 C12 1.4873(18) .
C4 C5 1.3867(19) .
C4 H4 0.9500 .
C5 C6 1.3992(19) .
C5 H5 0.9500 .
C6 C16 1.4913(18) 3_666
C7 C8 1.3844(18) .
C7 C12 1.4039(18) .
C7 H7 0.9500 .
C8 C9 1.4011(18) .
C8 H8 0.9500 .
C9 C10 1.4064(18) .
C9 C13 1.4904(18) .
C10 C11 1.3850(19) .
C10 H10 0.9500 .
C11 C12 1.4059(18) .
C11 H11 0.9500 .
C13 C18 1.3959(18) .
C13 C14 1.4073(18) .
C14 C15 1.3880(19) .
C14 H14 0.9500 .
C15 C16 1.4079(19) .
C15 H15 0.9500 .
C16 C17 1.3959(19) .
C17 C18 1.3869(19) .
C17 H17 0.9500 .
C18 H18 0.9500 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 71816689
