#------------------------------------------------------------------------------
#$Date: 2020-09-06 11:39:25 +0300 (Sun, 06 Sep 2020) $
#$Revision: 256033 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/68/7126844.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_7126844
loop_
_publ_author_name
'Yakiyama, Yumi'
'Fujinaka, Takahisa'
'Nishimura, Mio'
'Seki, Ryotaro'
'Sakurai, Hidehiro'
_publ_section_title
;
 Control by one drop of solvent: selective preparation of guest
 release/trap-triggered interconvertible molecular crystals.
;
_journal_issue                   67
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9687
_journal_page_last               9690
_journal_paper_doi               10.1039/d0cc03408h
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C14 H8 N O2, C2.25'
_chemical_formula_sum            'C16.25 H10.62 N O2'
_chemical_formula_weight         251.88
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-04-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-16 deposited with the CCDC.	2020-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.128(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.4912(5)
_cell_length_b                   18.1068(5)
_cell_length_c                   8.5193(3)
_cell_measurement_reflns_used    8926
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.8500
_cell_measurement_theta_min      2.2140
_cell_volume                     2371.16(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.849
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  76.00   0.50    7.67    --    5.49  38.00   0.00  160
  2  ω      4.00  70.00   0.50    7.67    --    5.49  77.00 120.00  132
  3  ω    -16.00  69.00   0.50    7.67    --    5.49  77.00  60.00  170
  4  ω    -12.00  36.00   0.50    7.67    --    5.49 -99.00 -90.00   96
  5  ω    -26.00  39.00   0.50    7.67    --    5.49 -99.00-120.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0101259000
_diffrn_orient_matrix_UB_12      0.0360156000
_diffrn_orient_matrix_UB_13      0.0294891000
_diffrn_orient_matrix_UB_21      0.0162430000
_diffrn_orient_matrix_UB_22      -0.0151403000
_diffrn_orient_matrix_UB_23      0.0746264000
_diffrn_orient_matrix_UB_31      0.0419906000
_diffrn_orient_matrix_UB_32      -0.0027839000
_diffrn_orient_matrix_UB_33      -0.0245292000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14587
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.792
_diffrn_reflns_theta_min         2.250
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       block
_exptl_crystal_F_000             1049
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3155
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0418
_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)+(0.0622P)²+1.4209P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1167
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2745
_reflns_number_total             3155
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc03408h2.cif
_cod_data_source_block           1aopen-toluene
_cod_depositor_comments
'Adding full bibliography for 7126838--7126851.cif.'
_cod_database_code               7126844
_shelx_shelxl_version_number     2018/3
_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 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: C1S(0.75) C2S(0.75) C3S(0.5) C4S(0.25)
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14)
;
_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 1.247
_oxdiff_exptl_absorpt_empirical_full_min 0.774
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
C1 C 0.54491(7) 0.66641(5) 0.71661(12) 0.0159(2) Uani 1 1 d . . . . .
C2 C 0.58997(7) 0.74206(6) 0.75060(13) 0.0178(2) Uani 1 1 d . . . . .
C3 C 0.61948(7) 0.76907(6) 0.60263(13) 0.0188(2) Uani 1 1 d . . . . .
C4 C 0.66869(8) 0.83127(6) 0.57804(14) 0.0240(2) Uani 1 1 d . . . . .
H4 H 0.689335 0.862336 0.661249 0.029 Uiso 1 1 calc R . . . .
C5 C 0.68587(8) 0.84531(7) 0.42499(15) 0.0278(3) Uani 1 1 d . . . . .
H5 H 0.718820 0.886446 0.405244 0.033 Uiso 1 1 calc R . . . .
C6 C 0.65457(8) 0.79880(7) 0.29979(14) 0.0263(3) Uani 1 1 d . . . . .
H6 H 0.667013 0.809570 0.198244 0.032 Uiso 1 1 calc R . . . .
C7 C 0.60530(7) 0.73687(6) 0.32430(13) 0.0212(2) Uani 1 1 d . . . . .
H7 H 0.584582 0.705784 0.241177 0.025 Uiso 1 1 calc R . . . .
C8 C 0.58807(7) 0.72304(6) 0.47769(13) 0.0179(2) Uani 1 1 d . . . . .
C9 C 0.53516(7) 0.66303(6) 0.53372(12) 0.0165(2) Uani 1 1 d . . . . .
C10 C 0.65579(8) 0.47898(7) 0.77634(15) 0.0271(3) Uani 1 1 d . . . . .
H10 H 0.646391 0.431179 0.738037 0.033 Uiso 1 1 calc R . . . .
C11 C 0.59730(8) 0.53312(6) 0.71792(13) 0.0214(2) Uani 1 1 d . . . . .
H11 H 0.551978 0.522037 0.639324 0.026 Uiso 1 1 calc R . . . .
C12 C 0.60743(7) 0.60438(6) 0.77867(12) 0.0173(2) Uani 1 1 d . . . . .
C13 C 0.67818(7) 0.61710(6) 0.89366(13) 0.0218(2) Uani 1 1 d . . . . .
H13 H 0.687342 0.663651 0.938787 0.026 Uiso 1 1 calc R . . . .
C14 C 0.73459(8) 0.55957(7) 0.93976(15) 0.0277(3) Uani 1 1 d . . . . .
H14 H 0.782324 0.569434 1.014252 0.033 Uiso 1 1 calc R . . . .
N1 N 0.72463(7) 0.49066(6) 0.88369(13) 0.0305(3) Uani 1 1 d . . . . .
O1 O 0.49271(5) 0.61809(4) 0.45226(9) 0.02076(19) Uani 1 1 d . . . . .
O2 O 0.59735(6) 0.77266(4) 0.87811(10) 0.0242(2) Uani 1 1 d . . . . .
C1S C 0.5229(2) 0.9381(2) 0.8592(8) 0.1168(19) Uani 0.75 1 d . . P . .
C2S C 0.52525(19) 0.92510(16) 1.0521(6) 0.0811(11) Uani 0.75 1 d . . P . .
C3S C 0.5021(6) 0.9750(5) 1.1596(13) 0.142(4) Uani 0.5 1 d . . P . .
C4S C 0.5661(18) 0.9996(10) 1.218(3) 0.166(9) Uani 0.25 1 d . . P . .
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_
_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
C2 C1 C1 109.39(6) . 2_656 ?
C9 C1 C1 112.66(10) . 2_656 ?
C9 C1 C2 102.04(8) . . ?
C12 C1 C1 115.21(7) . 2_656 ?
C12 C1 C2 109.43(8) . . ?
C12 C1 C9 107.26(8) . . ?
C3 C2 C1 108.27(9) . . ?
O2 C2 C1 124.20(10) . . ?
O2 C2 C3 127.52(10) . . ?
C4 C3 C2 129.09(10) . . ?
C4 C3 C8 121.08(10) . . ?
C8 C3 C2 109.80(9) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 C3 117.59(11) . . ?
C5 C4 H4 121.2 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.22(11) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.17(11) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 121.3 . . ?
C6 C7 C8 117.46(10) . . ?
C8 C7 H7 121.3 . . ?
C3 C8 C9 110.44(9) . . ?
C7 C8 C3 121.47(10) . . ?
C7 C8 C9 128.06(10) . . ?
C8 C9 C1 107.92(8) . . ?
O1 C9 C1 125.62(9) . . ?
O1 C9 C8 126.44(10) . . ?
C11 C10 H10 117.8 . . ?
N1 C10 H10 117.8 . . ?
N1 C10 C11 124.49(11) . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 118.95(11) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C1 120.90(9) . . ?
C11 C12 C13 117.16(10) . . ?
C13 C12 C1 121.91(9) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.21(11) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 118.0 . . ?
N1 C14 C13 124.01(11) . . ?
N1 C14 H14 118.0 . . ?
C10 N1 C14 116.11(10) . . ?
C2S C1S C1S 158.1(3) . 2_656 ?
C2S C1S C4S 111.5(9) . 5_677 ?
C2S C1S C4S 140.5(7) . 6_575 ?
C3S C1S C1S 81.3(4) 5_677 2_656 ?
C3S C1S C2S 102.1(5) 5_677 . ?
C3S C1S C4S 37.9(7) 5_677 5_677 ?
C3S C1S C4S 56.0(8) 5_677 6_575 ?
C4S C1S C1S 58.5(8) 5_677 2_656 ?
C4S C1S C1S 58.9(7) 6_575 2_656 ?
C4S C1S C4S 72.9(15) 6_575 5_677 ?
C1S C2S C4S 125.0(6) . . ?
C3S C2S C1S 126.6(5) . . ?
C3S C2S C4S 33.4(8) . . ?
C1S C3S C4S 68.5(9) 5_677 2_657 ?
C2S C3S C1S 130.9(8) . 5_677 ?
C2S C3S C3S 135.5(6) . 2_657 ?
C2S C3S C4S 148.3(10) . 2_657 ?
C3S C3S C1S 93.4(5) 2_657 5_677 ?
C3S C3S C4S 42.0(9) 2_657 2_657 ?
C4S C3S C1S 81.3(11) . 5_677 ?
C4S C3S C2S 105.4(16) . . ?
C4S C3S C3S 72.9(15) . 2_657 ?
C4S C3S C4S 102.1(19) . 2_657 ?
C1S C4S C1S 62.5(8) 6_576 5_677 ?
C1S C4S C2S 90.1(11) 5_677 . ?
C1S C4S C2S 140.3(16) 6_576 . ?
C3S C4S C1S 83.1(13) 2_657 5_677 ?
C3S C4S C1S 99.2(19) . 6_576 ?
C3S C4S C1S 55.5(9) 2_657 6_576 ?
C3S C4S C1S 60.7(12) . 5_677 ?
C3S C4S C2S 95.4(14) 2_657 . ?
C3S C4S C2S 41.1(11) . . ?
C3S C4S C3S 65.1(17) . 2_657 ?
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
C1 C1 1.567(2) 2_656 ?
C1 C2 1.5484(14) . ?
C1 C9 1.5478(14) . ?
C1 C12 1.5336(14) . ?
C2 C3 1.4766(15) . ?
C2 O2 1.2121(13) . ?
C3 C4 1.3904(15) . ?
C3 C8 1.3913(14) . ?
C4 H4 0.9300 . ?
C4 C5 1.3862(17) . ?
C5 H5 0.9300 . ?
C5 C6 1.3978(17) . ?
C6 H6 0.9300 . ?
C6 C7 1.3868(16) . ?
C7 H7 0.9300 . ?
C7 C8 1.3886(15) . ?
C8 C9 1.4757(14) . ?
C9 O1 1.2095(13) . ?
C10 H10 0.9300 . ?
C10 C11 1.3848(16) . ?
C10 N1 1.3328(17) . ?
C11 H11 0.9300 . ?
C11 C12 1.3919(15) . ?
C12 C13 1.3956(15) . ?
C13 H13 0.9300 . ?
C13 C14 1.3848(16) . ?
C14 H14 0.9300 . ?
C14 N1 1.3381(18) . ?
C1S C1S 1.906(13) 2_656 ?
C1S C2S 1.657(7) . ?
C1S C3S 1.624(10) 5_677 ?
C1S C4S 1.83(3) 6_575 ?
C1S C4S 1.84(2) 5_677 ?
C2S C3S 1.366(10) . ?
C2S C4S 2.00(3) . ?
C3S C3S 1.55(2) 2_657 ?
C3S C4S 1.63(3) 2_657 ?
C3S C4S 1.14(3) . ?
