#------------------------------------------------------------------------------
#$Date: 2024-03-01 03:22:47 +0100 (Fri 01 de Mar de 2024) $
#$Revision: 290016 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/82/7248234.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_7248234
loop_
_publ_author_name
'Seki, Tomohiro'
'Hattori, Kota'
_publ_section_title
;
 Mechanochromic aromatic hydrocarbons that bear one simple substituent
;
_journal_issue                   11
_journal_name_full               'RSC Advances'
_journal_page_first              7258
_journal_page_last               7262
_journal_paper_doi               10.1039/D3RA08519H
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C17 H9 N'
_chemical_formula_sum            'C17 H9 N'
_chemical_formula_weight         227.25
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-02
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-12-07 deposited with the CCDC.	2024-02-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.960(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.8023(2)
_cell_length_b                   17.9097(9)
_cell_length_c                   15.9061(8)
_cell_measurement_reflns_used    2317
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.6100
_cell_measurement_theta_min      3.7230
_cell_volume                     1080.59(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     40.00  67.00   0.50    0.51    --  107.20 -57.00 120.00   54
  2  ω     35.00  60.00   0.50    0.51    --  107.20 -57.00  90.00   50
  3  ω     35.00  64.00   0.50    0.51    --  107.20 -57.00  30.00   58
  4  ω     44.00  69.00   0.50    0.51    --  107.20 -57.00  60.00   50
  5  ω     35.00  67.00   0.50    0.51    --  107.20 -57.00 -90.00   64
  6  ω    117.00 152.00   0.50    0.51    --  107.20 107.00   4.00   70
  7  ω    -18.00  12.00   0.50    0.13    --   46.86 -19.00   0.00   60
  8  ω     10.00  81.00   0.50    0.13    --   46.86-107.00 -93.00  142
  9  ω     64.00  90.00   0.50    0.51    --  107.20-107.00 -93.00   52
 10  ω     67.00 106.00   0.50    0.51    --  107.20 -99.00  90.00   78
 11  ω     37.00  63.00   0.50    0.51    --  107.20 -99.00  90.00   52
 12  ω    -33.00  25.00   0.50    0.13    --  -46.86  38.00 120.00  116
 13  ω    -62.00 -37.00   0.50    0.51    -- -104.50  57.00   0.00   50
 14  ω    -61.00 -36.00   0.50    0.51    -- -104.50  57.00 -60.00   50
 15  ω    -22.00  26.00   0.50    0.13    --  -46.86  19.00-150.00   96
 16  ω    -18.00   7.00   0.50    0.13    --  -46.86  19.00-180.00   50
 17  ω    -62.00 -32.00   0.50    0.51    -- -104.50  57.00-150.00   60
 18  ω   -154.00-129.00   0.50    0.51    -- -104.50 -19.00 -60.00   50
 19  ω   -150.00 -85.00   0.50    0.51    -- -104.50-107.00 -93.00  130
 20  ω   -173.00 -94.00   0.50    0.51    -- -104.50 -19.00  90.00  158
 21  ω    -77.00 -50.00   0.50    0.13    --  -46.86 107.00   4.00   54
 22  ω   -106.00 -59.00   0.50    0.51    -- -104.50 107.00   4.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0118270000
_diffrn_orient_matrix_UB_12      -0.0592092000
_diffrn_orient_matrix_UB_13      -0.0704180000
_diffrn_orient_matrix_UB_21      -0.1459195000
_diffrn_orient_matrix_UB_22      0.0588269000
_diffrn_orient_matrix_UB_23      -0.0639849000
_diffrn_orient_matrix_UB_31      0.3784869000
_diffrn_orient_matrix_UB_32      0.0207757000
_diffrn_orient_matrix_UB_33      -0.0197074000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5540
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.081
_diffrn_reflns_theta_min         3.722
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.915
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2163
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0870
_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)+(0.1374P)²+1.1394P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2486
_refine_ls_wR_factor_ref         0.2583
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1798
_reflns_number_total             2163
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ra08519h2.cif
_cod_data_source_block           htr-4-ip_auto
_cod_database_code               7248234
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CN
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E),
 C00F(H00F), C00G(H00G), C00H(H00H)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.914
_oxdiff_exptl_absorpt_empirical_full_min 0.389
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N001 N 0.3688(7) 0.52154(14) 0.61076(15) 0.0322(6) Uani 1 1 d . . . . .
C002 C 0.4210(7) 0.45585(15) 0.74494(16) 0.0221(6) Uani 1 1 d . . . . .
C003 C 0.3572(7) 0.39010(14) 0.79150(16) 0.0216(6) Uani 1 1 d . . . . .
C004 C 0.1819(7) 0.32775(15) 0.75197(17) 0.0233(6) Uani 1 1 d . . . . .
C005 C 0.4640(7) 0.38721(15) 0.87900(16) 0.0239(6) Uani 1 1 d . . . . .
C006 C 0.1178(7) 0.26272(15) 0.79940(19) 0.0273(7) Uani 1 1 d . . . . .
C007 C 0.1401(7) 0.39727(16) 0.61811(17) 0.0256(6) Uani 1 1 d . . . . .
H007 H 0.067462 0.400151 0.559844 0.031 Uiso 1 1 calc R U . . .
C008 C 0.6382(7) 0.44891(16) 0.91640(17) 0.0276(7) Uani 1 1 d . . . . .
H008 H 0.716712 0.447047 0.974375 0.033 Uiso 1 1 calc R U . . .
C009 C 0.0740(7) 0.33053(15) 0.66409(17) 0.0249(6) Uani 1 1 d . . . . .
C00A C 0.3047(7) 0.45622(15) 0.65662(17) 0.0234(6) Uani 1 1 d . . . . .
C00B C 0.5921(7) 0.51651(15) 0.78526(18) 0.0262(6) Uani 1 1 d . . . . .
H00B H 0.636075 0.560505 0.754312 0.031 Uiso 1 1 calc R U . . .
C00C C 0.6976(7) 0.51248(16) 0.87023(18) 0.0281(7) Uani 1 1 d . . . . .
H00C H 0.812419 0.554033 0.897181 0.034 Uiso 1 1 calc R U . . .
C00D C 0.2252(8) 0.26145(16) 0.88763(19) 0.0310(7) Uani 1 1 d . . . . .
H00D H 0.179093 0.218443 0.920056 0.037 Uiso 1 1 calc R U . . .
C00E C 0.3914(8) 0.32076(17) 0.92532(18) 0.0302(7) Uani 1 1 d . . . . .
H00E H 0.461634 0.318346 0.983746 0.036 Uiso 1 1 calc R U . . .
C00F C -0.0929(8) 0.26854(16) 0.62605(19) 0.0295(7) Uani 1 1 d . . . . .
H00F H -0.166040 0.269975 0.567743 0.035 Uiso 1 1 calc R U . . .
C00G C -0.1525(8) 0.20554(17) 0.6721(2) 0.0330(7) Uani 1 1 d . . . . .
H00G H -0.262724 0.163535 0.645011 0.040 Uiso 1 1 calc R U . . .
C00H C -0.0533(8) 0.20228(16) 0.7582(2) 0.0332(7) Uani 1 1 d . . . . .
H00H H -0.102381 0.158612 0.789199 0.040 Uiso 1 1 calc R U . . .
C00I C 0.4192(10) 0.57636(19) 0.5740(2) 0.0400(8) Uani 1 1 d . . . . .
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'
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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00I N001 C00A 178.7(3) . . ?
C003 C002 C00A 117.3(2) . . ?
C00B C002 C003 119.7(2) . . ?
C00B C002 C00A 123.0(3) . . ?
C002 C003 C004 120.7(2) . . ?
C002 C003 C005 119.5(2) . . ?
C005 C003 C004 119.8(2) . . ?
C003 C004 C009 119.9(2) . . ?
C006 C004 C003 120.1(3) . . ?
C006 C004 C009 120.0(3) . . ?
C003 C005 C00E 118.7(3) . . ?
C008 C005 C003 118.8(2) . . ?
C008 C005 C00E 122.6(3) . . ?
C004 C006 C00D 119.1(3) . . ?
C00H C006 C004 118.5(3) . . ?
C00H C006 C00D 122.5(3) . . ?
C009 C007 H007 119.6 . . ?
C00A C007 H007 119.6 . . ?
C00A C007 C009 120.8(2) . . ?
C005 C008 H008 119.5 . . ?
C00C C008 C005 121.0(3) . . ?
C00C C008 H008 119.5 . . ?
C004 C009 C007 118.7(2) . . ?
C00F C009 C004 119.1(3) . . ?
C00F C009 C007 122.2(3) . . ?
N001 C00A C002 117.1(2) . . ?
C007 C00A N001 120.3(2) . . ?
C007 C00A C002 122.6(2) . . ?
C002 C00B H00B 120.0 . . ?
C00C C00B C002 120.1(3) . . ?
C00C C00B H00B 120.0 . . ?
C008 C00C C00B 121.0(3) . . ?
C008 C00C H00C 119.5 . . ?
C00B C00C H00C 119.5 . . ?
C006 C00D H00D 119.6 . . ?
C00E C00D C006 120.9(3) . . ?
C00E C00D H00D 119.6 . . ?
C005 C00E H00E 119.2 . . ?
C00D C00E C005 121.5(3) . . ?
C00D C00E H00E 119.2 . . ?
C009 C00F H00F 119.7 . . ?
C00G C00F C009 120.6(3) . . ?
C00G C00F H00F 119.7 . . ?
C00F C00G H00G 119.5 . . ?
C00F C00G C00H 121.0(3) . . ?
C00H C00G H00G 119.5 . . ?
C006 C00H H00H 119.6 . . ?
C00G C00H C006 120.8(3) . . ?
C00G C00H H00H 119.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N001 C00A 1.409(4) . ?
N001 C00I 1.165(4) . ?
C002 C003 1.421(4) . ?
C002 C00A 1.443(4) . ?
C002 C00B 1.399(4) . ?
C003 C004 1.424(4) . ?
C003 C005 1.424(4) . ?
C004 C006 1.418(4) . ?
C004 C009 1.430(4) . ?
C005 C008 1.400(4) . ?
C005 C00E 1.437(4) . ?
C006 C00D 1.434(4) . ?
C006 C00H 1.402(4) . ?
C007 H007 0.9500 . ?
C007 C009 1.433(4) . ?
C007 C00A 1.352(4) . ?
C008 H008 0.9500 . ?
C008 C00C 1.382(4) . ?
C009 C00F 1.396(4) . ?
C00B H00B 0.9500 . ?
C00B C00C 1.385(4) . ?
C00C H00C 0.9500 . ?
C00D H00D 0.9500 . ?
C00D C00E 1.355(5) . ?
C00E H00E 0.9500 . ?
C00F H00F 0.9500 . ?
C00F C00G 1.373(4) . ?
C00G H00G 0.9500 . ?
C00G C00H 1.396(5) . ?
C00H H00H 0.9500 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C002 C003 C004 C006 -179.5(2) . . . . ?
C002 C003 C004 C009 1.2(4) . . . . ?
C002 C003 C005 C008 -1.7(4) . . . . ?
C002 C003 C005 C00E 178.9(2) . . . . ?
C002 C00B C00C C008 0.4(4) . . . . ?
C003 C002 C00A N001 -180.0(2) . . . . ?
C003 C002 C00A C007 0.2(4) . . . . ?
C003 C002 C00B C00C -0.2(4) . . . . ?
C003 C004 C006 C00D 1.3(4) . . . . ?
C003 C004 C006 C00H -179.6(2) . . . . ?
C003 C004 C009 C007 -1.2(4) . . . . ?
C003 C004 C009 C00F 179.1(2) . . . . ?
C003 C005 C008 C00C 1.8(4) . . . . ?
C003 C005 C00E C00D 0.0(4) . . . . ?
C004 C003 C005 C008 179.5(2) . . . . ?
C004 C003 C005 C00E 0.1(4) . . . . ?
C004 C006 C00D C00E -1.2(4) . . . . ?
C004 C006 C00H C00G 1.2(4) . . . . ?
C004 C009 C00F C00G -0.2(4) . . . . ?
C005 C003 C004 C006 -0.8(4) . . . . ?
C005 C003 C004 C009 179.9(2) . . . . ?
C005 C008 C00C C00B -1.2(4) . . . . ?
C006 C004 C009 C007 179.5(2) . . . . ?
C006 C004 C009 C00F -0.2(4) . . . . ?
C006 C00D C00E C005 0.5(4) . . . . ?
C007 C009 C00F C00G -179.9(2) . . . . ?
C008 C005 C00E C00D -179.4(3) . . . . ?
C009 C004 C006 C00D -179.4(2) . . . . ?
C009 C004 C006 C00H -0.3(4) . . . . ?
C009 C007 C00A N001 179.9(2) . . . . ?
C009 C007 C00A C002 -0.3(4) . . . . ?
C009 C00F C00G C00H 1.1(4) . . . . ?
C00A C002 C003 C004 -0.7(4) . . . . ?
C00A C002 C003 C005 -179.4(2) . . . . ?
C00A C002 C00B C00C -179.9(2) . . . . ?
C00A C007 C009 C004 0.7(4) . . . . ?
C00A C007 C009 C00F -179.5(3) . . . . ?
C00B C002 C003 C004 179.7(2) . . . . ?
C00B C002 C003 C005 0.9(4) . . . . ?
C00B C002 C00A N001 -0.3(4) . . . . ?
C00B C002 C00A C007 179.8(2) . . . . ?
C00D C006 C00H C00G -179.7(2) . . . . ?
C00E C005 C008 C00C -178.8(2) . . . . ?
C00F C00G C00H C006 -1.6(4) . . . . ?
C00H C006 C00D C00E 179.7(3) . . . . ?
