#------------------------------------------------------------------------------
#$Date: 2020-09-06 11:39:25 +0300 (Sun, 06 Sep 2020) $
#$Revision: 256033 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/68/7126850.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_7126850
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, C1.5'
_chemical_formula_sum            'C15.5 H11.3 N O2'
_chemical_formula_weight         243.55
_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
_atom_sites_solution_primary     dual
_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                 97.664(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.4960(3)
_cell_length_b                   17.8919(3)
_cell_length_c                   8.5454(2)
_cell_measurement_reflns_used    20036
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.1740
_cell_measurement_theta_min      2.3390
_cell_volume                     2348.07(8)
_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 0.878
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  14.00   0.50    5.27    --   -5.34  19.00   0.00   60
  2  ω     17.00  70.00   0.50    5.27    --   -5.34  19.00   0.00  106
  3  ω     31.00  57.00   0.50    5.27    --   -5.34  33.00 -38.91   52
  4  ω    -18.00  68.00   0.50    5.27    --   -5.34  33.00  43.00  172
  5  ω    -18.00  66.00   0.50    5.27    --   -5.34  30.00-129.86  168
  6  ω    -24.00  19.00   0.50    5.27    --   -5.34 -99.00-120.00   86
  7  ω    -25.00  28.00   0.50    5.27    --   -5.34 -99.00 -60.00  106
  8  ω    -26.00  19.00   0.50    5.27    --   -5.34 -99.00  90.00   90
  9  ω    -18.00  69.00   0.50    5.27    --   -5.34  19.00 -90.00  174
 10  ω    -18.00  60.00   0.50    5.27    --   -5.34  19.00-180.00  156
 11  ω    -18.00  24.00   0.50    5.27    --   -5.34  33.00 -38.91   84
 12  ω    -18.00  67.00   0.50    5.27    --   -5.34  36.00  88.23  170
;
_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      0.0154417000
_diffrn_orient_matrix_UB_12      0.0365850000
_diffrn_orient_matrix_UB_13      0.0196928000
_diffrn_orient_matrix_UB_21      0.0288282000
_diffrn_orient_matrix_UB_22      -0.0146360000
_diffrn_orient_matrix_UB_23      0.0641422000
_diffrn_orient_matrix_UB_31      0.0326065000
_diffrn_orient_matrix_UB_32      -0.0043546000
_diffrn_orient_matrix_UB_33      -0.0501448000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            29902
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.983
_diffrn_reflns_theta_min         2.277
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87854
_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    1.378
_exptl_crystal_description       block
_exptl_crystal_F_000             1018
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         3290
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0426
_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)+(0.0623P)²+1.8435P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1200
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3007
_reflns_number_total             3290
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc03408h2.cif
_cod_data_source_block           1aopen-decane
_cod_depositor_comments
'Adding full bibliography for 7126838--7126851.cif.'
_cod_original_formula_sum        'C15.50 H11.30 N O2'
_cod_database_code               7126850
_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.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 1.183
_oxdiff_exptl_absorpt_empirical_full_min 0.791
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 0.54468(6) 0.32996(5) 0.71663(11) 0.01454(19) Uani 1 1 d . . . . .
C2 C 0.58943(7) 0.25297(6) 0.74760(12) 0.0167(2) Uani 1 1 d . . . . .
C3 C 0.61841(7) 0.22699(6) 0.59917(12) 0.0182(2) Uani 1 1 d . . . . .
C4 C 0.66693(8) 0.16397(6) 0.57202(14) 0.0241(2) Uani 1 1 d . . . . .
H4 H 0.687511 0.131603 0.653699 0.029 Uiso 1 1 calc R . . . .
C5 C 0.68348(8) 0.15118(7) 0.41849(15) 0.0282(3) Uani 1 1 d . . . . .
H5 H 0.715784 0.109504 0.397022 0.034 Uiso 1 1 calc R . . . .
C6 C 0.65250(8) 0.19977(7) 0.29562(14) 0.0264(2) Uani 1 1 d . . . . .
H6 H 0.664389 0.189772 0.193859 0.032 Uiso 1 1 calc R . . . .
C7 C 0.60432(7) 0.26265(6) 0.32297(12) 0.0209(2) Uani 1 1 d . . . . .
H7 H 0.584132 0.295312 0.241597 0.025 Uiso 1 1 calc R . . . .
C8 C 0.58734(7) 0.27500(6) 0.47639(12) 0.0173(2) Uani 1 1 d . . . . .
C9 C 0.53466(6) 0.33530(5) 0.53428(11) 0.01526(19) Uani 1 1 d . . . . .
C10 C 0.65826(8) 0.51846(6) 0.78372(14) 0.0246(2) Uani 1 1 d . . . . .
H10 H 0.649758 0.567111 0.746539 0.029 Uiso 1 1 calc R . . . .
C11 C 0.59882(7) 0.46444(6) 0.72282(13) 0.0199(2) Uani 1 1 d . . . . .
H11 H 0.553628 0.476509 0.644010 0.024 Uiso 1 1 calc R . . . .
C12 C 0.60792(6) 0.39190(6) 0.78154(12) 0.0159(2) Uani 1 1 d . . . . .
C13 C 0.67844(7) 0.37775(6) 0.89749(13) 0.0200(2) Uani 1 1 d . . . . .
H13 H 0.686898 0.330323 0.941405 0.024 Uiso 1 1 calc R . . . .
C14 C 0.73555(7) 0.43518(7) 0.94617(14) 0.0249(2) Uani 1 1 d . . . . .
H14 H 0.783026 0.424356 1.021289 0.030 Uiso 1 1 calc R . . . .
N1 N 0.72681(7) 0.50519(6) 0.89214(13) 0.0273(2) Uani 1 1 d . . . . .
O1 O 0.49246(5) 0.38157(4) 0.45457(9) 0.01960(17) Uani 1 1 d . . . . .
O2 O 0.59706(6) 0.22080(4) 0.87363(9) 0.02282(18) Uani 1 1 d . . . . .
C1S C 0.5048(6) 0.0161(3) 0.0849(18) 0.265(7) Uani 1 1 d . . . . .
C2S C 0.500000 -0.0176(4) 0.250000 0.286(10) Uani 1 2 d S T 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 109.58(6) . 2_656 ?
C9 C1 C1 113.06(10) . 2_656 ?
C9 C1 C2 102.09(7) . . ?
C12 C1 C1 114.94(7) . 2_656 ?
C12 C1 C2 109.33(8) . . ?
C12 C1 C9 107.04(8) . . ?
C3 C2 C1 108.29(8) . . ?
O2 C2 C1 124.20(9) . . ?
O2 C2 C3 127.51(10) . . ?
C4 C3 C2 129.16(10) . . ?
C8 C3 C2 109.83(9) . . ?
C8 C3 C4 120.98(10) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 C3 117.57(10) . . ?
C5 C4 H4 121.2 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.26(10) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 121.09(10) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 121.2 . . ?
C6 C7 C8 117.52(10) . . ?
C8 C7 H7 121.2 . . ?
C3 C8 C9 110.45(9) . . ?
C7 C8 C3 121.57(9) . . ?
C7 C8 C9 127.95(9) . . ?
C8 C9 C1 107.83(8) . . ?
O1 C9 C1 125.74(9) . . ?
O1 C9 C8 126.41(9) . . ?
C11 C10 H10 117.8 . . ?
N1 C10 H10 117.8 . . ?
N1 C10 C11 124.30(11) . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 118.95(10) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C1 120.96(9) . . ?
C11 C12 C13 117.17(9) . . ?
C13 C12 C1 121.83(9) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.16(10) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 117.9 . . ?
N1 C14 C13 124.15(11) . . ?
N1 C14 H14 117.9 . . ?
C10 N1 C14 116.20(10) . . ?
C2S C1S C1S 134.3(6) . 5_655 ?
C1S C2S C1S 134.1(8) . 2_655 ?
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 1.5664(19) 2_656 ?
C1 C2 1.5490(13) . ?
C1 C9 1.5482(13) . ?
C1 C12 1.5333(13) . ?
C2 C3 1.4760(14) . ?
C2 O2 1.2129(13) . ?
C3 C4 1.3917(14) . ?
C3 C8 1.3914(14) . ?
C4 H4 0.9300 . ?
C4 C5 1.3890(16) . ?
C5 H5 0.9300 . ?
C5 C6 1.3979(17) . ?
C6 H6 0.9300 . ?
C6 C7 1.3872(15) . ?
C7 H7 0.9300 . ?
C7 C8 1.3888(14) . ?
C8 C9 1.4774(13) . ?
C9 O1 1.2075(12) . ?
C10 H10 0.9300 . ?
C10 C11 1.3876(15) . ?
C10 N1 1.3344(16) . ?
C11 H11 0.9300 . ?
C11 C12 1.3919(14) . ?
C12 C13 1.3969(14) . ?
C13 H13 0.9300 . ?
C13 C14 1.3834(15) . ?
C14 H14 0.9300 . ?
C14 N1 1.3356(17) . ?
C1S C1S 1.55(3) 5_655 ?
C1S C2S 1.545(14) . ?
