#------------------------------------------------------------------------------
#$Date: 2017-03-04 10:07:37 +0200 (Sat, 04 Mar 2017) $
#$Revision: 193274 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/22/4032291.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_4032291
loop_
_publ_author_name
'Huang, Changfeng'
'Li, Shuangjiang'
'Thakellapalli, Haresh'
'Farajidizaji, Behzad'
'Huang, Yiwei'
'Akhmedov, Novruz G.'
'Popp, Brian V.'
'Petersen, Jeffrey L.'
'Wang, Kung K.'
_publ_section_title
;
 Synthesis of Partially Hydrogenated Cycloparaphenylenes with Bent and
 Fused Structures Bearing Armchair Carbon Nanotube-like Connections.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1166
_journal_page_last               1174
_journal_paper_doi               10.1021/acs.joc.6b02789
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C40 H30 Br4 O2'
_chemical_formula_weight         862.28
_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
_cell_angle_alpha                113.5216(14)
_cell_angle_beta                 102.0238(15)
_cell_angle_gamma                94.4772(16)
_cell_formula_units_Z            1
_cell_length_a                   9.5245(5)
_cell_length_b                   9.7842(5)
_cell_length_c                   10.2374(5)
_cell_measurement_reflns_used    7506
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      30.1372
_cell_measurement_theta_min      2.9025
_cell_volume                     841.62(8)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker AXS D8 Venture fixed chi'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  Triumph
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_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            15495
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.18
_exptl_absorpt_coefficient_mu    4.817
_exptl_absorpt_correction_T_max  0.51
_exptl_absorpt_correction_T_min  0.19
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS V2014/3 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelopiped
_exptl_crystal_F_000             426
_exptl_crystal_size_max          0.428
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.164
_refine_diff_density_max         1.223
_refine_diff_density_min         -0.957
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3829
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0471
_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)+(0.0264P)²+1.9344P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.1073
_reflns_number_gt                2629
_reflns_number_total             3829
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo6b02789_si_001.cif
_cod_data_source_block           compound_6
_cod_original_cell_volume        841.62(7)
_cod_database_code               4032291
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
Br Br1 0.12933(8) 0.26568(7) 0.67303(6) 0.0849(2) Uani d . . 1
Br Br2 0.46823(6) 0.99057(6) 0.80293(5) 0.06669(18) Uani d . . 1
O O1 -0.1532(3) 0.2356(3) -0.0264(3) 0.0385(6) Uani d . . 1
C C1 -0.0773(4) 0.3700(3) -0.0120(3) 0.0286(7) Uani d . . 1
C C2 0.0735(4) 0.4021(4) 0.0460(3) 0.0283(7) Uani d . . 1
C C3 0.1504(4) 0.2850(4) 0.0792(3) 0.0313(8) Uani d . . 1
H H3 0.1034 0.1856 -0.0007 0.038 Uiso calc U R 1
C C4 0.3076(4) 0.3074(5) 0.0785(4) 0.0405(9) Uani d . . 1
H H4 0.3555 0.2252 0.0622 0.049 Uiso calc U R 1
C C5 0.3813(5) 0.4366(5) 0.0995(4) 0.0428(9) Uani d . . 1
H H5 0.4781 0.441 0.0953 0.051 Uiso calc U R 1
C C6 0.3166(4) 0.5772(4) 0.1301(4) 0.0325(8) Uani d . . 1
H H6 0.3588 0.6329 0.0821 0.039 Uiso calc U R 1
C C7 0.1525(4) 0.5361(4) 0.0614(3) 0.0282(7) Uani d . . 1
C C8 0.1386(4) 0.2792(4) 0.2241(4) 0.0323(8) Uani d . . 1
C C9 0.1181(5) 0.1427(4) 0.2334(4) 0.0450(10) Uani d . . 1
H H9 0.1085 0.0531 0.1499 0.054 Uiso calc U R 1
C C10 0.1115(5) 0.1366(5) 0.3648(5) 0.0545(11) Uani d . . 1
H H10 0.0957 0.0437 0.3693 0.065 Uiso calc U R 1
C C11 0.1285(5) 0.2694(5) 0.4886(4) 0.0463(10) Uani d . . 1
C C12 0.1487(5) 0.4058(4) 0.4824(4) 0.0430(9) Uani d . . 1
H H12 0.1605 0.4951 0.5668 0.052 Uiso calc U R 1
C C13 0.1515(4) 0.4109(4) 0.3497(4) 0.0366(8) Uani d . . 1
H H13 0.1621 0.5039 0.345 0.044 Uiso calc U R 1
C C14 0.3563(4) 0.6814(4) 0.2972(4) 0.0327(8) Uani d . . 1
C C15 0.4587(5) 0.6541(6) 0.3965(5) 0.0609(13) Uani d . . 1
H H15 0.5064 0.5727 0.3617 0.073 Uiso calc U R 1
C C16 0.4921(5) 0.7447(6) 0.5469(5) 0.0651(14) Uani d . . 1
H H16 0.5606 0.7237 0.6123 0.078 Uiso calc U R 1
C C17 0.4239(4) 0.8644(5) 0.5974(4) 0.0425(9) Uani d . . 1
C C18 0.3238(6) 0.8946(6) 0.5026(5) 0.0737(16) Uani d . . 1
H H18 0.277 0.9767 0.5379 0.088 Uiso calc U R 1
C C19 0.2913(6) 0.8026(5) 0.3523(5) 0.0646(14) Uani d . . 1
H H19 0.223 0.8248 0.2877 0.078 Uiso calc U R 1
C C20 -0.2147(5) 0.2499(5) 0.0939(5) 0.0506(11) Uani d . . 1
H H20A -0.141 0.3027 0.1854 0.076 Uiso calc U R 1
H H20B -0.2512 0.151 0.0838 0.076 Uiso calc U R 1
H H20C -0.2932 0.3057 0.0929 0.076 Uiso calc U R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C1 O1 C20 . . 114.6(3)
O1 C1 C7 . 2_565 119.4(3)
O1 C1 C2 . . 118.1(3)
C7 C1 C2 2_565 . 122.5(3)
C1 C2 C7 . . 119.3(3)
C1 C2 C3 . . 119.5(3)
C7 C2 C3 . . 121.0(3)
C4 C3 C2 . . 111.3(3)
C4 C3 C8 . . 109.7(3)
C2 C3 C8 . . 114.1(3)
C5 C4 C3 . . 123.5(3)
C4 C5 C6 . . 122.9(4)
C5 C6 C7 . . 110.2(3)
C5 C6 C14 . . 111.3(3)
C7 C6 C14 . . 112.3(3)
C1 C7 C2 2_565 . 118.2(3)
C1 C7 C6 2_565 . 121.4(3)
C2 C7 C6 . . 120.5(3)
C9 C8 C13 . . 118.3(3)
C9 C8 C3 . . 120.8(3)
C13 C8 C3 . . 120.9(3)
C8 C9 C10 . . 121.2(4)
C11 C10 C9 . . 119.2(4)
C12 C11 C10 . . 120.8(4)
C12 C11 Br1 . . 118.8(3)
C10 C11 Br1 . . 120.3(3)
C11 C12 C13 . . 119.7(4)
C12 C13 C8 . . 120.8(3)
C19 C14 C15 . . 117.3(4)
C19 C14 C6 . . 121.4(3)
C15 C14 C6 . . 121.3(3)
C14 C15 C16 . . 121.6(4)
C17 C16 C15 . . 119.2(4)
C18 C17 C16 . . 120.5(4)
C18 C17 Br2 . . 119.5(3)
C16 C17 Br2 . . 120.0(3)
C17 C18 C19 . . 119.7(4)
C14 C19 C18 . . 121.7(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C11 . 1.902(4)
Br2 C17 . 1.899(4)
O1 C1 . 1.388(4)
O1 C20 . 1.433(5)
C1 C7 2_565 1.391(5)
C1 C2 . 1.392(5)
C2 C7 . 1.394(5)
C2 C3 . 1.517(4)
C3 C4 . 1.499(5)
C3 C8 . 1.534(5)
C4 C5 . 1.311(6)
C5 C6 . 1.497(5)
C6 C7 . 1.522(5)
C6 C14 . 1.546(5)
C7 C1 2_565 1.391(5)
C8 C9 . 1.378(5)
C8 C13 . 1.384(5)
C9 C10 . 1.385(6)
C10 C11 . 1.374(6)
C11 C12 . 1.362(6)
C12 C13 . 1.384(5)
C14 C19 . 1.355(6)
C14 C15 . 1.378(5)
C15 C16 . 1.385(6)
C16 C17 . 1.355(6)
C17 C18 . 1.351(6)
C18 C19 . 1.388(6)
