#------------------------------------------------------------------------------
#$Date: 2019-11-24 03:30:50 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236504 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/40/1554053.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_1554053
loop_
_publ_author_name
'Hariharan, P. S.'
'Venkataramanan, N. S.'
'Moon, Dohyun'
'Anthony, Savarimuthu Philip'
_publ_section_title
;
 Self-Reversible Mechanochromism and Thermochromism of a
 Triphenylamine-Based Molecule: Tunable Fluorescence and Nanofabrication
 Studies
;
_journal_issue                   17
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_page_first              9460
_journal_paper_doi               10.1021/acs.jpcc.5b00310
_journal_volume                  119
_journal_year                    2015
_chemical_formula_moiety         'C20 H17 N O2'
_chemical_formula_sum            'C20 H17 N O2'
_chemical_formula_weight         303.35
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 97.76(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.194(2)
_cell_length_b                   11.472(2)
_cell_length_c                   13.683(3)
_cell_measurement_reflns_used    51423
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.547
_cell_measurement_theta_min      0.361
_cell_volume                     1585.5(6)
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_collection
'PAL ADSC Quantum-210 ADX Program (Arvai & Nielsen, 1983)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, L. J. 2012)'
_computing_publication_material  'EnCifer 1.5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.62998
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16058
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        22.209
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.787
_diffrn_source                   'PLSII 2D bending magnet'
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.993
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'HKL3000sm Scalepack'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4366
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0393
_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)+(0.0701P)²+0.4292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1158
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3788
_reflns_number_total             4366
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp5b00310_si_002.cif
_cod_data_source_block           SPA6
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1554053
_shelx_shelxl_version_number     2014/7
_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   0.994
_shelx_estimated_absorpt_t_max   0.996
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
O1 O 1.02133(7) 0.74761(6) 0.62308(6) 0.01790(16) Uani 1 1 d . .
O2 O 0.34571(7) 0.28091(7) 0.15241(5) 0.01730(16) Uani 1 1 d . .
N1 N 0.69806(7) 0.27104(7) 0.50234(6) 0.01021(16) Uani 1 1 d . .
C1 C 1.01678(9) 0.64940(8) 0.65700(7) 0.01340(18) Uani 1 1 d . .
H1 H 1.0755 0.6326 0.7153 0.016 Uiso 1 1 calc R U
C2 C 0.92950(9) 0.55567(8) 0.61621(7) 0.01017(17) Uani 1 1 d . .
C3 C 0.92803(9) 0.45135(8) 0.66928(7) 0.01130(17) Uani 1 1 d . .
H3 H 0.9823 0.4441 0.7311 0.014 Uiso 1 1 calc R U
C4 C 0.84916(9) 0.35883(8) 0.63326(7) 0.01078(17) Uani 1 1 d . .
H4 H 0.8473 0.2899 0.6715 0.013 Uiso 1 1 calc R U
C5 C 0.77147(8) 0.36621(8) 0.54004(6) 0.00881(17) Uani 1 1 d . .
C6 C 0.77055(9) 0.47238(8) 0.48732(6) 0.01067(17) Uani 1 1 d . .
H6 H 0.7164 0.4802 0.4255 0.013 Uiso 1 1 calc R U
C7 C 0.84818(9) 0.56491(8) 0.52544(7) 0.01106(17) Uani 1 1 d . .
H7 H 0.8463 0.6359 0.4895 0.013 Uiso 1 1 calc R U
C8 C 0.22676(11) 0.34729(11) 0.14526(8) 0.0228(2) Uani 1 1 d . .
H8A H 0.1700 0.3164 0.1916 0.034 Uiso 1 1 calc R U
H8B H 0.1802 0.3423 0.0779 0.034 Uiso 1 1 calc R U
H8C H 0.2482 0.4289 0.1614 0.034 Uiso 1 1 calc R U
C9 C 0.42741(9) 0.28418(8) 0.24038(7) 0.01176(18) Uani 1 1 d . .
C10 C 0.40033(9) 0.34569(9) 0.32312(7) 0.01408(19) Uani 1 1 d . .
H10 H 0.3216 0.3905 0.3207 0.017 Uiso 1 1 calc R U
C11 C 0.49015(9) 0.34078(8) 0.40978(7) 0.01372(19) Uani 1 1 d . .
H11 H 0.4709 0.3807 0.4670 0.016 Uiso 1 1 calc R U
C12 C 0.60703(8) 0.27821(8) 0.41308(6) 0.00978(17) Uani 1 1 d . .
C13 C 0.63433(9) 0.21819(8) 0.32938(7) 0.01150(17) Uani 1 1 d . .
H13 H 0.7147 0.1759 0.3311 0.014 Uiso 1 1 calc R U
C14 C 0.54457(9) 0.22013(8) 0.24367(7) 0.01305(18) Uani 1 1 d . .
H14 H 0.5627 0.1780 0.1872 0.016 Uiso 1 1 calc R U
C15 C 0.77499(10) -0.06711(8) 0.61642(7) 0.01483(19) Uani 1 1 d . .
H15 H 0.7922 -0.1431 0.6427 0.018 Uiso 1 1 calc R U
C16 C 0.64809(10) -0.02098(9) 0.60839(7) 0.01595(19) Uani 1 1 d . .
H16 H 0.5783 -0.0659 0.6286 0.019 Uiso 1 1 calc R U
C17 C 0.62252(9) 0.09078(8) 0.57086(7) 0.01272(18) Uani 1 1 d . .
H17 H 0.5355 0.1221 0.5653 0.015 Uiso 1 1 calc R U
C18 C 0.72514(9) 0.15632(7) 0.54150(6) 0.00912(17) Uani 1 1 d . .
C19 C 0.85256(9) 0.11002(8) 0.54797(6) 0.01041(17) Uani 1 1 d . .
H19 H 0.9221 0.1544 0.5267 0.012 Uiso 1 1 calc R U
C20 C 0.87703(9) -0.00160(8) 0.58577(7) 0.01182(18) Uani 1 1 d . .
H20 H 0.9638 -0.0333 0.5907 0.014 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 0.0020 0.0010 '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 0.0050 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0090 0.0050 '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
C9 O2 C8 117.21(8)
C5 N1 C12 121.86(7)
C5 N1 C18 121.20(7)
C12 N1 C18 116.17(7)
O1 C1 C2 125.96(9)
O1 C1 H1 117.0
C2 C1 H1 117.0
C3 C2 C7 118.53(8)
C3 C2 C1 118.71(8)
C7 C2 C1 122.76(8)
C4 C3 C2 121.19(8)
C4 C3 H3 119.4
C2 C3 H3 119.4
C3 C4 C5 120.34(8)
C3 C4 H4 119.8
C5 C4 H4 119.8
N1 C5 C4 119.95(8)
N1 C5 C6 121.55(8)
C4 C5 C6 118.50(8)
C7 C6 C5 120.28(8)
C7 C6 H6 119.9
C5 C6 H6 119.9
C6 C7 C2 121.07(8)
C6 C7 H7 119.5
C2 C7 H7 119.5
O2 C8 H8A 109.5
O2 C8 H8B 109.5
H8A C8 H8B 109.5
O2 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O2 C9 C10 124.39(8)
O2 C9 C14 115.45(8)
C10 C9 C14 120.16(9)
C9 C10 C11 119.34(8)
C9 C10 H10 120.3
C11 C10 H10 120.3
C12 C11 C10 120.67(9)
C12 C11 H11 119.7
C10 C11 H11 119.7
C11 C12 C13 119.62(8)
C11 C12 N1 120.81(8)
C13 C12 N1 119.53(8)
C14 C13 C12 120.26(8)
C14 C13 H13 119.9
C12 C13 H13 119.9
C13 C14 C9 119.93(9)
C13 C14 H14 120.0
C9 C14 H14 120.0
C16 C15 C20 119.75(9)
C16 C15 H15 120.1
C20 C15 H15 120.1
C15 C16 C17 120.41(9)
C15 C16 H16 119.8
C17 C16 H16 119.8
C18 C17 C16 119.57(9)
C18 C17 H17 120.2
C16 C17 H17 120.2
C17 C18 C19 120.40(8)
C17 C18 N1 119.33(8)
C19 C18 N1 120.26(8)
C20 C19 C18 119.53(8)
C20 C19 H19 120.2
C18 C19 H19 120.2
C19 C20 C15 120.32(9)
C19 C20 H20 119.8
C15 C20 H20 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2219(12)
O2 C9 1.3686(11)
O2 C8 1.4240(13)
N1 C5 1.3834(11)
N1 C12 1.4330(12)
N1 C18 1.4336(11)
C1 C2 1.4578(13)
C1 H1 0.9500
C2 C3 1.4009(13)
C2 C7 1.4010(13)
C3 C4 1.3816(12)
C3 H3 0.9500
C4 C5 1.4102(12)
C4 H4 0.9500
C5 C6 1.4149(12)
C6 C7 1.3834(13)
C6 H6 0.9500
C7 H7 0.9500
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 C10 1.3929(13)
C9 C14 1.3978(13)
C10 C11 1.3979(13)
C10 H10 0.9500
C11 C12 1.3865(12)
C11 H11 0.9500
C12 C13 1.3962(13)
C13 C14 1.3869(13)
C13 H13 0.9500
C14 H14 0.9500
C15 C16 1.3882(14)
C15 C20 1.3930(13)
C15 H15 0.9500
C16 C17 1.3926(14)
C16 H16 0.9500
C17 C18 1.3908(12)
C17 H17 0.9500
C18 C19 1.3950(12)
C19 C20 1.3908(13)
C19 H19 0.9500
C20 H20 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C19 H19 O1 0.95 2.47 3.2575(13) 139.9 3_766
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
O1 C1 C2 C3 -174.12(9)
O1 C1 C2 C7 6.76(15)
C7 C2 C3 C4 0.41(13)
C1 C2 C3 C4 -178.75(8)
C2 C3 C4 C5 2.25(14)
C12 N1 C5 C4 173.24(8)
C18 N1 C5 C4 -17.17(12)
C12 N1 C5 C6 -6.51(13)
C18 N1 C5 C6 163.08(8)
C3 C4 C5 N1 176.67(8)
C3 C4 C5 C6 -3.57(13)
N1 C5 C6 C7 -177.95(8)
C4 C5 C6 C7 2.29(13)
C5 C6 C7 C2 0.33(13)
C3 C2 C7 C6 -1.71(13)
C1 C2 C7 C6 177.42(8)
C8 O2 C9 C10 1.45(14)
C8 O2 C9 C14 -178.55(9)
O2 C9 C10 C11 178.75(9)
C14 C9 C10 C11 -1.25(14)
C9 C10 C11 C12 1.84(15)
C10 C11 C12 C13 -0.91(14)
C10 C11 C12 N1 -178.73(9)
C5 N1 C12 C11 -70.15(12)
C18 N1 C12 C11 119.77(10)
C5 N1 C12 C13 112.03(10)
C18 N1 C12 C13 -58.05(11)
C11 C12 C13 C14 -0.62(14)
N1 C12 C13 C14 177.22(8)
C12 C13 C14 C9 1.21(14)
O2 C9 C14 C13 179.74(8)
C10 C9 C14 C13 -0.26(14)
C20 C15 C16 C17 -0.67(15)
C15 C16 C17 C18 -0.12(15)
C16 C17 C18 C19 1.05(14)
C16 C17 C18 N1 179.61(8)
C5 N1 C18 C17 127.63(9)
C12 N1 C18 C17 -62.22(11)
C5 N1 C18 C19 -53.81(12)
C12 N1 C18 C19 116.34(9)
C17 C18 C19 C20 -1.19(13)
N1 C18 C19 C20 -179.73(8)
C18 C19 C20 C15 0.39(13)
C16 C15 C20 C19 0.53(14)
