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#$Date: 2025-08-20 21:34:49 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301835 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/16/4131688.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_4131688
loop_
_publ_author_name
'Jordan, Robert S.'
'Li, Yolanda L.'
'Lin, Cheng-Wei'
'McCurdy, Ryan D.'
'Lin, Janice B.'
'Brosmer, Jonathan L.'
'Marsh, Kristofer L.'
'Khan, Saeed I.'
'Houk, K. N.'
'Kaner, Richard B.'
'Rubin, Yves'
_publ_section_title
;
 Synthesis of N = 8 Armchair Graphene Nanoribbons from Four Distinct
 Polydiacetylenes.
;
_journal_issue                   44
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15878
_journal_page_last               15890
_journal_paper_doi               10.1021/jacs.7b08800
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C24 H24 N2 O2'
_chemical_formula_sum            'C24 H24 N2 O2'
_chemical_formula_weight         372.45
_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   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                88.299(2)
_cell_angle_beta                 89.480(1)
_cell_angle_gamma                81.756(2)
_cell_formula_units_Z            1
_cell_length_a                   4.7918(2)
_cell_length_b                   5.4310(2)
_cell_length_c                   19.0454(7)
_cell_measurement_reflns_used    4264
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.84
_cell_measurement_theta_min      2.32
_cell_volume                     490.30(3)
_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-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.949
_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  0.0295
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6355
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.164
_diffrn_reflns_theta_min         2.321
_diffrn_source                   'I\mS micro--focus source'
_exptl_absorpt_coefficient_mu    0.638
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       platelet
_exptl_crystal_F_000             198
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1744
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0701P)²+0.1201P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1115
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1599
_reflns_number_total             1744
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b08800_si_004.cif
_cod_data_source_block           cu_yr1704c_s
_cod_database_code               4131688
_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   0.832
_shelx_estimated_absorpt_t_max   0.987
_shelxl_version_number           2014/6
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
O1 O 0.60195(18) 0.31267(17) 0.80496(5) 0.0252(3) Uani 1 1 d . .
N1 N 0.1502(2) 0.44891(18) 0.77164(5) 0.0177(3) Uani 1 1 d . .
H1N H -0.027(4) 0.433(3) 0.7803(8) 0.021 Uiso 1 1 d . U
C1 C 0.8940(2) 0.5392(2) 0.52306(6) 0.0188(3) Uani 1 1 d . .
C2 C 0.7070(3) 0.6100(2) 0.56394(6) 0.0191(3) Uani 1 1 d . .
C3 C 0.4854(2) 0.6920(2) 0.61222(6) 0.0179(3) Uani 1 1 d . .
C4 C 0.3232(3) 0.9263(2) 0.60346(6) 0.0203(3) Uani 1 1 d . .
H4 H 0.3621 1.0352 0.5658 0.024 Uiso 1 1 calc R U
C5 C 0.1058(3) 0.9980(2) 0.65007(6) 0.0210(3) Uani 1 1 d . .
H5 H -0.0061 1.1562 0.6438 0.025 Uiso 1 1 calc R U
C6 C 0.0482(3) 0.8422(2) 0.70606(6) 0.0190(3) Uani 1 1 d . .
H6 H -0.1018 0.8934 0.7377 0.023 Uiso 1 1 calc R U
C7 C 0.2126(3) 0.6110(2) 0.71517(6) 0.0169(3) Uani 1 1 d . .
C8 C 0.4285(3) 0.5342(2) 0.66834(6) 0.0179(3) Uani 1 1 d . .
H8 H 0.5377 0.3747 0.6743 0.022 Uiso 1 1 calc R U
C9 C 0.3472(3) 0.3078(2) 0.81185(6) 0.0176(3) Uani 1 1 d . .
C10 C 0.2313(3) 0.1461(2) 0.86876(6) 0.0199(3) Uani 1 1 d . .
H10 H 0.0633 0.0811 0.8497 0.024 Uiso 1 1 calc R U
C11 C 0.4507(3) -0.0740(2) 0.88983(7) 0.0283(3) Uani 1 1 d . .
H11A H 0.6165 -0.0132 0.9089 0.042 Uiso 1 1 calc R U
H11B H 0.5062 -0.1733 0.8485 0.042 Uiso 1 1 calc R U
H11C H 0.3707 -0.1774 0.9256 0.042 Uiso 1 1 calc R U
C12 C 0.1366(3) 0.3067(2) 0.93172(7) 0.0289(3) Uani 1 1 d . .
H12A H 0.0559 0.2053 0.9679 0.043 Uiso 1 1 calc R U
H12B H -0.0060 0.4454 0.9166 0.043 Uiso 1 1 calc R U
H12C H 0.2991 0.3721 0.9510 0.043 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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
C9 N1 C7 124.43(11) .
C9 N1 H1N 116.9(10) .
C7 N1 H1N 118.7(10) .
C2 C1 C1 179.60(17) 2_766
C1 C2 C3 179.61(13) .
C4 C3 C8 119.82(11) .
C4 C3 C2 120.77(11) .
C8 C3 C2 119.40(10) .
C5 C4 C3 119.44(11) .
C5 C4 H4 120.3 .
C3 C4 H4 120.3 .
C4 C5 C6 121.05(11) .
C4 C5 H5 119.5 .
C6 C5 H5 119.5 .
C7 C6 C5 119.32(11) .
C7 C6 H6 120.3 .
C5 C6 H6 120.3 .
C8 C7 C6 120.45(11) .
C8 C7 N1 120.10(10) .
C6 C7 N1 119.40(11) .
C7 C8 C3 119.90(10) .
C7 C8 H8 120.0 .
C3 C8 H8 120.0 .
O1 C9 N1 123.16(11) .
O1 C9 C10 121.54(11) .
N1 C9 C10 115.27(10) .
C11 C10 C9 110.79(10) .
C11 C10 C12 111.45(11) .
C9 C10 C12 109.00(10) .
C11 C10 H10 108.5 .
C9 C10 H10 108.5 .
C12 C10 H10 108.5 .
C10 C11 H11A 109.5 .
C10 C11 H11B 109.5 .
H11A C11 H11B 109.5 .
C10 C11 H11C 109.5 .
H11A C11 H11C 109.5 .
H11B C11 H11C 109.5 .
C10 C12 H12A 109.5 .
C10 C12 H12B 109.5 .
H12A C12 H12B 109.5 .
C10 C12 H12C 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C9 1.2307(15) .
N1 C9 1.3546(16) .
N1 C7 1.4262(15) .
N1 H1N 0.881(17) .
C1 C2 1.2095(18) .
C1 C1 1.367(2) 2_766
C2 C3 1.4291(17) .
C3 C4 1.3989(17) .
C3 C8 1.3995(17) .
C4 C5 1.3831(18) .
C4 H4 0.9500 .
C5 C6 1.3917(17) .
C5 H5 0.9500 .
C6 C7 1.3906(17) .
C6 H6 0.9500 .
C7 C8 1.3862(17) .
C8 H8 0.9500 .
C9 C10 1.5253(16) .
C10 C11 1.5212(17) .
C10 C12 1.5307(18) .
C10 H10 1.0000 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 157861017
