#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:05:33 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257738 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/94/7059491.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_7059491
loop_
_publ_author_name
'Morita, Masato'
'Yamada, Shigeyuki'
'Konno, Tsutomu'
_publ_section_title
;
 Fluorine-induced emission enhancement of tolanes via formation of tight
 molecular aggregates
;
_journal_issue                   17
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6704
_journal_page_last               6708
_journal_paper_doi               10.1039/D0NJ01268H
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C16 H11 N O'
_chemical_formula_sum            'C16 H11 N O'
_chemical_formula_weight         233.26
_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             2019-09-27
_audit_creation_method
;
Olex2 1.3
(compiled Sep 10 2019 10:52:38 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2020-02-05 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.747(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0792(3)
_cell_length_b                   7.7395(3)
_cell_length_c                   28.2605(15)
_cell_measurement_reflns_used    6237
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.8440
_cell_measurement_theta_min      2.7010
_cell_volume                     1273.26(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  24.00   0.25    3.84    --  -11.80  57.00  22.00  104
  2  ω    -47.00 -10.00   0.25    3.84    --  -11.80  57.00  22.00  148
  3  ω    -84.00  92.00   0.25    3.84    --    5.00  19.00 -60.00  704
  4  ω      8.00  33.00   0.25    3.84    --    5.00  57.00  22.00  100
  5  ω      0.00  26.00   0.25    3.84    --  -11.80  57.00 -60.00  104
  6  ω    -47.00  71.00   0.25    3.84    --  -11.80  57.00  90.00  472
  7  ω    -36.00 -10.00   0.25    3.84    --  -11.80  57.00 -60.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0577469000
_diffrn_orient_matrix_UB_12      -0.0411841000
_diffrn_orient_matrix_UB_13      -0.0154479000
_diffrn_orient_matrix_UB_21      -0.0683515000
_diffrn_orient_matrix_UB_22      0.0467532000
_diffrn_orient_matrix_UB_23      -0.0206144000
_diffrn_orient_matrix_UB_31      0.0827509000
_diffrn_orient_matrix_UB_32      0.0671333000
_diffrn_orient_matrix_UB_33      0.0048734000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            14685
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.737
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.671
_exptl_crystal_size_mid          0.584
_exptl_crystal_size_min          0.139
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0466
_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)+(0.0755P)²+0.0957P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1533
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2005
_reflns_number_total             2908
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj01268h2.cif
_cod_data_source_block           c1-4h-cn
_cod_depositor_comments
;Adding full bibliography for 7059490--7059495.cif.

 Adding full bibliography for 7059490--7059495.cif.
;
_cod_database_code               7059491
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C16H11NO
_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.
;
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C008(H008), C009(H009), C00B(H00B), C00C(H00C), C00D(H00D),
 C00E(H00E), C00F(H00F)
2.b Idealised Me refined as rotating group:
 C00I(H00A,H00G,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 1.737
_oxdiff_exptl_absorpt_empirical_full_min 0.405
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
O1 O -0.0291(2) 0.38591(15) 0.43486(4) 0.0955(4) Uani 1 1 d . . . . .
C002 C 0.3572(2) 0.38076(16) 0.18042(5) 0.0659(3) Uani 1 1 d . . . . .
C003 C 0.1441(2) 0.37838(16) 0.30340(5) 0.0674(4) Uani 1 1 d . . . . .
C004 C 0.5285(2) 0.36292(17) 0.09972(5) 0.0683(4) Uani 1 1 d . . . . .
C005 C 0.0378(2) 0.38086(17) 0.39293(5) 0.0706(4) Uani 1 1 d . . . . .
C006 C -0.0624(2) 0.44900(17) 0.30694(5) 0.0718(4) Uani 1 1 d . . . . .
H006 H -0.166233 0.495782 0.279024 0.086 Uiso 1 1 calc R U . . .
C10 C 0.2714(3) 0.38538(18) 0.22240(6) 0.0735(4) Uani 1 1 d . . . . .
C008 C -0.1130(2) 0.44992(18) 0.35089(6) 0.0742(4) Uani 1 1 d . . . . .
H008 H -0.250919 0.497658 0.352617 0.089 Uiso 1 1 calc R U . . .
C009 C 0.5646(2) 0.29705(18) 0.18378(5) 0.0718(4) Uani 1 1 d . . . . .
H009 H 0.646453 0.246480 0.213482 0.086 Uiso 1 1 calc R U . . .
C00A C 0.2076(3) 0.38211(17) 0.25865(5) 0.0734(4) Uani 1 1 d . . . . .
C00B C 0.2387(2) 0.45559(18) 0.13576(5) 0.0725(4) Uani 1 1 d . . . . .
H00B H 0.100670 0.512295 0.133009 0.087 Uiso 1 1 calc R U . . .
C00C C 0.6483(2) 0.28867(18) 0.14398(5) 0.0716(4) Uani 1 1 d . . . . .
H00C H 0.786708 0.232649 0.146700 0.086 Uiso 1 1 calc R U . . .
C00D C 0.2928(2) 0.30881(18) 0.34596(5) 0.0737(4) Uani 1 1 d . . . . .
H00D H 0.429907 0.259584 0.344294 0.088 Uiso 1 1 calc R U . . .
C00E C 0.2438(2) 0.31041(19) 0.39032(5) 0.0753(4) Uani 1 1 d . . . . .
H00E H 0.347675 0.264739 0.418410 0.090 Uiso 1 1 calc R U . . .
C00F C 0.3219(2) 0.4472(2) 0.09565(5) 0.0751(4) Uani 1 1 d . . . . .
H00F H 0.240688 0.497596 0.065867 0.090 Uiso 1 1 calc R U . . .
C00G C 0.6214(3) 0.3540(2) 0.05847(6) 0.0843(4) Uani 1 1 d . . . . .
N00H N 0.6984(3) 0.3466(3) 0.02614(6) 0.1165(6) Uani 1 1 d . . . . .
C00I C 0.1247(4) 0.3225(3) 0.47926(7) 0.1162(7) Uani 1 1 d . . . . .
H00A H 0.159102 0.203469 0.475039 0.174 Uiso 1 1 calc R U . . .
H00G H 0.055090 0.332406 0.505622 0.174 Uiso 1 1 calc R U . . .
H00H H 0.264024 0.388880 0.487177 0.174 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 11 4 0.3051
6 7 -1 0.3523
-6 -7 1 0.2127
-5 8 5 0.3132
7 7 -2 0.3503
-7 -6 2 0.2091
6 -8 -9 0.3358
0 1 -38 0.0702
-6 -8 -1 0.2450
0 0 38 0.0497
3 -5 -36 0.2182
6 0 -34 0.3364
7 7 -11 0.3573
2 -2 -39 0.1255
4 7 17 0.3050
6 5 -31 0.3131
-1 0 39 0.0746
1 0 -39 0.0663
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
C005 O1 C00I 118.34(13) . . ?
C009 C002 C10 119.62(12) . . ?
C00B C002 C10 121.84(12) . . ?
C00B C002 C009 118.54(13) . . ?
C006 C003 C00A 122.25(12) . . ?
C00D C003 C006 117.60(13) . . ?
C00D C003 C00A 120.11(12) . . ?
C00C C004 C00F 119.94(13) . . ?
C00C C004 C00G 119.20(12) . . ?
C00F C004 C00G 120.86(12) . . ?
O1 C005 C008 116.55(12) . . ?
O1 C005 C00E 123.98(13) . . ?
C008 C005 C00E 119.46(13) . . ?
C003 C006 H006 119.7 . . ?
C008 C006 C003 120.67(12) . . ?
C008 C006 H006 119.7 . . ?
C00A C10 C002 176.43(15) . . ?
C005 C008 H008 119.6 . . ?
C006 C008 C005 120.87(12) . . ?
C006 C008 H008 119.6 . . ?
C002 C009 H009 119.7 . . ?
C00C C009 C002 120.70(12) . . ?
C00C C009 H009 119.7 . . ?
C10 C00A C003 176.94(14) . . ?
C002 C00B H00B 119.5 . . ?
C00F C00B C002 120.97(12) . . ?
C00F C00B H00B 119.5 . . ?
C004 C00C H00C 119.9 . . ?
C009 C00C C004 120.24(12) . . ?
C009 C00C H00C 119.9 . . ?
C003 C00D H00D 119.0 . . ?
C00E C00D C003 122.05(12) . . ?
C00E C00D H00D 119.0 . . ?
C005 C00E H00E 120.3 . . ?
C00D C00E C005 119.33(13) . . ?
C00D C00E H00E 120.3 . . ?
C004 C00F H00F 120.2 . . ?
C00B C00F C004 119.62(12) . . ?
C00B C00F H00F 120.2 . . ?
N00H C00G C004 179.02(16) . . ?
O1 C00I H00A 109.5 . . ?
O1 C00I H00G 109.5 . . ?
O1 C00I H00H 109.5 . . ?
H00A C00I H00G 109.5 . . ?
H00A C00I H00H 109.5 . . ?
H00G C00I H00H 109.5 . . ?
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
O1 C005 1.3595(17) . ?
O1 C00I 1.419(2) . ?
C002 C10 1.427(2) . ?
C002 C009 1.3962(19) . ?
C002 C00B 1.3868(18) . ?
C003 C006 1.399(2) . ?
C003 C00A 1.4249(19) . ?
C003 C00D 1.3880(19) . ?
C004 C00C 1.3785(18) . ?
C004 C00F 1.3902(19) . ?
C004 C00G 1.436(2) . ?
C005 C008 1.382(2) . ?
C005 C00E 1.387(2) . ?
C006 H006 0.9300 . ?
C006 C008 1.3629(19) . ?
C10 C00A 1.1956(19) . ?
C008 H008 0.9300 . ?
C009 H009 0.9300 . ?
C009 C00C 1.3630(19) . ?
C00B H00B 0.9300 . ?
C00B C00F 1.3695(19) . ?
C00C H00C 0.9300 . ?
C00D H00D 0.9300 . ?
C00D C00E 1.3693(19) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00G N00H 1.142(2) . ?
C00I H00A 0.9600 . ?
C00I H00G 0.9600 . ?
C00I H00H 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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C005 C008 C006 -179.23(12) . . . . ?
O1 C005 C00E C00D 178.73(12) . . . . ?
C002 C009 C00C C004 -0.1(2) . . . . ?
C002 C00B C00F C004 -0.2(2) . . . . ?
C003 C006 C008 C005 -0.2(2) . . . . ?
C003 C00D C00E C005 1.1(2) . . . . ?
C006 C003 C00D C00E -1.0(2) . . . . ?
C10 C002 C009 C00C 179.01(12) . . . . ?
C10 C002 C00B C00F -178.86(13) . . . . ?
C008 C005 C00E C00D -0.8(2) . . . . ?
C009 C002 C00B C00F 0.32(19) . . . . ?
C00A C003 C006 C008 -177.10(12) . . . . ?
C00A C003 C00D C00E 176.66(12) . . . . ?
C00B C002 C009 C00C -0.19(19) . . . . ?
C00C C004 C00F C00B -0.1(2) . . . . ?
C00D C003 C006 C008 0.51(19) . . . . ?
C00E C005 C008 C006 0.3(2) . . . . ?
C00F C004 C00C C009 0.2(2) . . . . ?
C00G C004 C00C C009 179.34(13) . . . . ?
C00G C004 C00F C00B -179.20(13) . . . . ?
C00I O1 C005 C008 -177.56(15) . . . . ?
C00I O1 C005 C00E 2.9(2) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.9890 10.6090 3.9727 -0.6132 0.5501 0.5670
6.2114 7.2264 -0.8780 0.0746 -0.0686 0.9948
-6.3090 -7.0839 0.9649 -0.0875 0.0801 -0.9929
-5.4628 8.3727 4.9793 -0.7372 0.6622 0.1343
6.5051 6.8387 -1.7948 0.1217 -0.0879 0.9887
-6.7821 -6.3948 2.2612 -0.1632 0.1180 -0.9795
5.7354 -8.0891 -9.0699 0.8045 -0.5832 -0.1126
0.2800 0.6580 -38.4278 0.5827 0.8038 -0.1199
-5.5800 -7.9685 -0.6058 0.0153 0.0213 -0.9997
0.2513 0.1055 37.7883 -0.5736 -0.7912 0.2120
3.0000 -5.0000 -36.0009 0.9353 0.3033 -0.2629
6.0000 -0.0000 -34.0008 0.8717 0.2908 0.3308
7.0000 7.0000 -11.0001 0.2859 0.0756 0.9956
2.0000 -2.0000 -39.0009 0.8003 0.5738 -0.1588
4.0000 7.0000 17.0005 -0.3199 -0.2966 0.8838
6.0000 5.0000 -31.0006 0.6195 0.4627 0.6811
-1.0000 0.0000 39.0009 -0.6602 -0.7356 0.1073
1.0000 -0.0000 -39.0009 0.6602 0.7356 -0.1073
