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#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/44/7124413.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_7124413
loop_
_publ_author_name
'Aguilar-Granda, Andrés'
'Colin-Molina, Abraham'
'Jellen, Marcus'
'Nuñez-Pineda, Alejandra'
'Cifuentes Quintal, Miguel Eduardo'
'Toscano, Rubén A.'
'Merino, Gabriel'
'Rodríguez-Molina, Braulio'
_publ_section_title
;
 Triggering the Dynamics of a Carbazole-p-[phenylene-diethynyl]-xylene
 Rotor through a Mechanically Induced Phase Transition
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC05672F
_journal_year                    2019
_chemical_formula_moiety         C28H21N
_chemical_formula_sum            'C28 H21 N'
_chemical_formula_weight         371.46
_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
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-07-13 deposited with the CCDC.    2019-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                115.448(2)
_cell_angle_beta                 90.572(2)
_cell_angle_gamma                97.252(2)
_cell_formula_units_Z            2
_cell_length_a                   5.5357(5)
_cell_length_b                   13.9222(14)
_cell_length_c                   15.0956(15)
_cell_measurement_reflns_used    2748
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      0.995
_cell_measurement_theta_min      0.984
_cell_volume                     1039.44(18)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX2 CCD area detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20975
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.122
_diffrn_reflns_theta_min         1.637
_exptl_absorpt_coefficient_mu    0.068
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: p-xylene'
_exptl_crystal_size_max          0.433
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.113
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         5594
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1280
_refine_ls_R_factor_gt           0.0551
_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)+(0.0461P)²+0.1358P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1437
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2748
_reflns_number_total             5594
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc05672f5.cif
_cod_data_source_block           2-p_Xylene
_cod_database_code               7124413
_shelx_shelxl_version_number     2016/6
_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   0.971
_shelx_estimated_absorpt_t_max   0.995
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
C1 C 0.4701(3) 0.37331(15) -0.12377(13) 0.0582(5) Uani 1 1 d . .
H1 H 0.370961 0.417189 -0.079280 0.070 Uiso 1 1 calc R U
C2 C 0.6314(4) 0.41239(17) -0.17355(14) 0.0686(6) Uani 1 1 d . .
H2 H 0.640395 0.483852 -0.162502 0.082 Uiso 1 1 calc R U
C3 C 0.7805(4) 0.3477(2) -0.23964(15) 0.0745(6) Uani 1 1 d . .
H3 H 0.888671 0.376516 -0.271690 0.089 Uiso 1 1 calc R U
C4 C 0.7705(4) 0.24192(19) -0.25829(13) 0.0687(6) Uani 1 1 d . .
H4 H 0.870106 0.198784 -0.303165 0.082 Uiso 1 1 calc R U
C5 C 0.6467(5) -0.00150(19) -0.25921(16) 0.0820(7) Uani 1 1 d . .
H5 H 0.764638 -0.007849 -0.304091 0.098 Uiso 1 1 calc R U
C6 C 0.5566(5) -0.0877(2) -0.24289(19) 0.0991(8) Uani 1 1 d . .
H6 H 0.614787 -0.152850 -0.276493 0.119 Uiso 1 1 calc R U
C7 C 0.3793(5) -0.07972(19) -0.1769(2) 0.0960(8) Uani 1 1 d . .
H7 H 0.318561 -0.140058 -0.167921 0.115 Uiso 1 1 calc R U
C8 C 0.2907(4) 0.01614(17) -0.12407(17) 0.0818(7) Uani 1 1 d . .
H8 H 0.172555 0.021523 -0.079437 0.098 Uiso 1 1 calc R U
N9 N 0.3244(3) 0.20829(12) -0.09945(10) 0.0552(4) Uani 1 1 d . .
C10 C 0.4608(3) 0.26650(14) -0.14233(11) 0.0497(4) Uani 1 1 d . .
C11 C 0.6097(3) 0.19953(15) -0.20941(12) 0.0548(5) Uani 1 1 d . .
C12 C 0.5609(3) 0.09624(16) -0.20815(13) 0.0592(5) Uani 1 1 d . .
C13 C 0.3851(4) 0.10381(15) -0.14037(13) 0.0595(5) Uani 1 1 d . .
C14 C 0.1956(3) 0.25383(14) -0.01340(12) 0.0505(4) Uani 1 1 d . .
C15 C 0.2560(4) 0.23781(17) 0.06819(14) 0.0652(5) Uani 1 1 d . .
H15 H 0.379168 0.197405 0.066132 0.078 Uiso 1 1 calc R U
C16 C 0.1338(4) 0.28159(17) 0.15203(14) 0.0659(5) Uani 1 1 d . .
H16 H 0.176025 0.270726 0.206474 0.079 Uiso 1 1 calc R U
C17 C -0.0517(3) 0.34184(14) 0.15674(13) 0.0532(5) Uani 1 1 d . .
C18 C -0.1082(3) 0.35809(14) 0.07483(12) 0.0544(5) Uani 1 1 d . .
H18 H -0.230407 0.398952 0.076781 0.065 Uiso 1 1 calc R U
C19 C 0.0142(3) 0.31449(14) -0.00931(12) 0.0529(4) Uani 1 1 d . .
H19 H -0.025809 0.326102 -0.063552 0.064 Uiso 1 1 calc R U
C20 C -0.1793(3) 0.38548(15) 0.24535(13) 0.0568(5) Uani 1 1 d . .
C21 C -0.2797(3) 0.41807(14) 0.31883(13) 0.0564(5) Uani 1 1 d . .
C22 C -0.3938(3) 0.45815(13) 0.41073(12) 0.0500(4) Uani 1 1 d . .
C23 C -0.3329(3) 0.42573(13) 0.48324(13) 0.0502(4) Uani 1 1 d . .
C24 C -0.5583(3) 0.53083(14) 0.42866(12) 0.0536(5) Uani 1 1 d . .
H24 H -0.596745 0.551066 0.379582 0.064 Uiso 1 1 calc R U
C25 C -0.1553(4) 0.34769(16) 0.46645(15) 0.0691(6) Uani 1 1 d . .
H25A H -0.217072 0.280460 0.411957 0.104 Uiso 1 1 calc R U
H25B H -0.134084 0.336626 0.524422 0.104 Uiso 1 1 calc R U
H25C H -0.001131 0.376027 0.452240 0.104 Uiso 1 1 calc R U
C31 C 0.1433(3) 0.09779(16) 0.51761(14) 0.0605(5) Uani 1 1 d . .
C32 C -0.0743(4) 0.06419(17) 0.46092(15) 0.0678(5) Uani 1 1 d . .
H32 H -0.127062 0.106992 0.433512 0.081 Uiso 1 1 calc R U
C33 C -0.2154(4) -0.03164(17) 0.44410(14) 0.0672(5) Uani 1 1 d . .
H33 H -0.362356 -0.051988 0.406045 0.081 Uiso 1 1 calc R U
C34 C 0.2975(4) 0.20272(19) 0.5367(2) 0.0959(8) Uani 1 1 d . .
H34A H 0.467070 0.195091 0.539185 0.144 Uiso 1 1 calc R U
H34B H 0.261087 0.257627 0.598286 0.144 Uiso 1 1 calc R U
H34C H 0.262750 0.222387 0.484738 0.144 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 0.0033 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'
N N 0.0061 0.0033 '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
C2 C1 C10 117.67(18) .
C2 C1 H1 121.2 .
C10 C1 H1 121.2 .
C1 C2 C3 121.6(2) .
C1 C2 H2 119.2 .
C3 C2 H2 119.2 .
C4 C3 C2 120.75(18) .
C4 C3 H3 119.6 .
C2 C3 H3 119.6 .
C3 C4 C11 119.35(19) .
C3 C4 H4 120.3 .
C11 C4 H4 120.3 .
C6 C5 C12 119.5(2) .
C6 C5 H5 120.3 .
C12 C5 H5 120.3 .
C5 C6 C7 120.9(2) .
C5 C6 H6 119.6 .
C7 C6 H6 119.6 .
C8 C7 C6 121.5(2) .
C8 C7 H7 119.3 .
C6 C7 H7 119.3 .
C7 C8 C13 117.3(2) .
C7 C8 H8 121.3 .
C13 C8 H8 121.3 .
C10 N9 C13 107.93(14) .
C10 N9 C14 125.13(14) .
C13 N9 C14 125.26(15) .
C1 C10 N9 129.50(16) .
C1 C10 C11 121.61(16) .
N9 C10 C11 108.82(15) .
C4 C11 C10 119.06(18) .
C4 C11 C12 133.73(18) .
C10 C11 C12 107.16(15) .
C5 C12 C13 119.1(2) .
C5 C12 C11 133.82(19) .
C13 C12 C11 107.10(16) .
C8 C13 C12 121.78(19) .
C8 C13 N9 129.20(18) .
C12 C13 N9 108.98(16) .
C19 C14 C15 119.50(16) .
C19 C14 N9 121.16(16) .
C15 C14 N9 119.33(16) .
C16 C15 C14 120.05(18) .
C16 C15 H15 120.0 .
C14 C15 H15 120.0 .
C15 C16 C17 121.05(18) .
C15 C16 H16 119.5 .
C17 C16 H16 119.5 .
C18 C17 C16 118.21(16) .
C18 C17 C20 122.00(17) .
C16 C17 C20 119.79(17) .
C19 C18 C17 120.89(17) .
C19 C18 H18 119.6 .
C17 C18 H18 119.6 .
C14 C19 C18 120.29(16) .
C14 C19 H19 119.9 .
C18 C19 H19 119.9 .
C21 C20 C17 177.2(2) .
C20 C21 C22 177.8(2) .
C24 C22 C23 120.06(15) .
C24 C22 C21 120.19(16) .
C23 C22 C21 119.73(16) .
C24 C23 C22 117.44(16) 2_466
C24 C23 C25 121.10(17) 2_466
C22 C23 C25 121.45(16) .
C23 C24 C22 122.49(16) 2_466
C23 C24 H24 118.8 2_466
C22 C24 H24 118.8 .
C23 C25 H25A 109.5 .
C23 C25 H25B 109.5 .
H25A C25 H25B 109.5 .
C23 C25 H25C 109.5 .
H25A C25 H25C 109.5 .
H25B C25 H25C 109.5 .
C33 C31 C32 117.48(18) 2_556
C33 C31 C34 121.1(2) 2_556
C32 C31 C34 121.4(2) .
C33 C32 C31 121.19(19) .
C33 C32 H32 119.4 .
C31 C32 H32 119.4 .
C31 C33 C32 121.33(19) 2_556
C31 C33 H33 119.3 2_556
C32 C33 H33 119.3 .
C31 C34 H34A 109.5 .
C31 C34 H34B 109.5 .
H34A C34 H34B 109.5 .
C31 C34 H34C 109.5 .
H34A C34 H34C 109.5 .
H34B C34 H34C 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 1.379(2) .
C1 C10 1.384(2) .
C1 H1 0.9300 .
C2 C3 1.385(3) .
C2 H2 0.9300 .
C3 C4 1.369(3) .
C3 H3 0.9300 .
C4 C11 1.393(3) .
C4 H4 0.9300 .
C5 C6 1.363(3) .
C5 C12 1.393(3) .
C5 H5 0.9300 .
C6 C7 1.385(3) .
C6 H6 0.9300 .
C7 C8 1.384(3) .
C7 H7 0.9300 .
C8 C13 1.387(3) .
C8 H8 0.9300 .
N9 C10 1.397(2) .
N9 C13 1.402(2) .
N9 C14 1.422(2) .
C10 C11 1.405(2) .
C11 C12 1.438(3) .
C12 C13 1.399(2) .
C14 C19 1.377(2) .
C14 C15 1.388(2) .
C15 C16 1.374(2) .
C15 H15 0.9300 .
C16 C17 1.390(2) .
C16 H16 0.9300 .
C17 C18 1.389(2) .
C17 C20 1.444(2) .
C18 C19 1.378(2) .
C18 H18 0.9300 .
C19 H19 0.9300 .
C20 C21 1.178(2) .
C21 C22 1.441(2) .
C22 C24 1.389(2) .
C22 C23 1.404(2) .
C23 C24 1.384(2) 2_466
C23 C25 1.500(2) .
C24 H24 0.9300 .
C25 H25A 0.9600 .
C25 H25B 0.9600 .
C25 H25C 0.9600 .
C31 C33 1.374(3) 2_556
C31 C32 1.377(3) .
C31 C34 1.505(3) .
C32 C33 1.377(3) .
C32 H32 0.9300 .
C33 H33 0.9300 .
C34 H34A 0.9600 .
C34 H34B 0.9600 .
C34 H34C 0.9600 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C10 C1 C2 C3 -0.3(3) . .
C1 C2 C3 C4 0.6(3) . .
C2 C3 C4 C11 -0.6(3) . .
C12 C5 C6 C7 0.6(4) . .
C5 C6 C7 C8 -1.1(4) . .
C6 C7 C8 C13 0.5(4) . .
C2 C1 C10 N9 176.73(17) . .
C2 C1 C10 C11 0.0(3) . .
C13 N9 C10 C1 -177.73(18) . .
C14 N9 C10 C1 -11.9(3) . .
C13 N9 C10 C11 -0.65(19) . .
C14 N9 C10 C11 165.14(16) . .
C3 C4 C11 C10 0.2(3) . .
C3 C4 C11 C12 -176.9(2) . .
C1 C10 C11 C4 0.0(3) . .
N9 C10 C11 C4 -177.31(16) . .
C1 C10 C11 C12 177.86(16) . .
N9 C10 C11 C12 0.51(19) . .
C6 C5 C12 C13 0.6(3) . .
C6 C5 C12 C11 -178.0(2) . .
C4 C11 C12 C5 -4.1(4) . .
C10 C11 C12 C5 178.5(2) . .
C4 C11 C12 C13 177.2(2) . .
C10 C11 C12 C13 -0.2(2) . .
C7 C8 C13 C12 0.7(3) . .
C7 C8 C13 N9 178.1(2) . .
C5 C12 C13 C8 -1.3(3) . .
C11 C12 C13 C8 177.64(18) . .
C5 C12 C13 N9 -179.13(17) . .
C11 C12 C13 N9 -0.2(2) . .
C10 N9 C13 C8 -177.1(2) . .
C14 N9 C13 C8 17.1(3) . .
C10 N9 C13 C12 0.5(2) . .
C14 N9 C13 C12 -165.22(16) . .
C10 N9 C14 C19 59.3(2) . .
C13 N9 C14 C19 -137.32(19) . .
C10 N9 C14 C15 -119.9(2) . .
C13 N9 C14 C15 43.4(3) . .
C19 C14 C15 C16 0.5(3) . .
N9 C14 C15 C16 179.77(17) . .
C14 C15 C16 C17 0.3(3) . .
C15 C16 C17 C18 -1.0(3) . .
C15 C16 C17 C20 179.07(18) . .
C16 C17 C18 C19 0.8(3) . .
C20 C17 C18 C19 -179.21(16) . .
C15 C14 C19 C18 -0.7(3) . .
N9 C14 C19 C18 -179.90(15) . .
C17 C18 C19 C14 0.0(3) . .
C24 C22 C23 C24 -0.3(3) . 2_466
C21 C22 C23 C24 178.00(16) . 2_466
C24 C22 C23 C25 -179.79(16) . .
C21 C22 C23 C25 -1.5(3) . .
C23 C22 C24 C23 0.3(3) . 2_466
C21 C22 C24 C23 -177.98(16) . 2_466
C33 C31 C32 C33 0.6(3) 2_556 .
C34 C31 C32 C33 -179.67(19) . .
C31 C32 C33 C31 -0.6(3) . 2_556
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168351084
