#------------------------------------------------------------------------------
#$Date: 2020-09-06 11:39:25 +0300 (Sun, 06 Sep 2020) $
#$Revision: 256033 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/68/7126843.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_7126843
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, C0.8'
_chemical_formula_sum            'C14.93 H9.9 N O2'
_chemical_formula_weight         235.34
_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             2018-12-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-26 deposited with the CCDC.	2020-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.99(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.564(3)
_cell_length_b                   18.062(4)
_cell_length_c                   8.5078(17)
_cell_measurement_reflns_used    23812
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.527
_cell_measurement_theta_min      2.795
_cell_volume                     2373.9(9)
_computing_cell_refinement       'HKL3000 (Minor et al., 2006)'
_computing_data_collection       'HKL3000 (Minor et al., 2006)'
_computing_data_reduction        'HKL3000 (Minor et al., 2006)'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  'Si(111) double crystal monochromator'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            23410
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         29.527
_diffrn_reflns_theta_min         2.795
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       block
_exptl_crystal_F_000             980
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3402
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0734
_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)+(0.1428P)²+2.0158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2079
_refine_ls_wR_factor_ref         0.2120
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3078
_reflns_number_total             3402
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc03408h2.cif
_cod_data_source_block           c2c
_cod_depositor_comments
'Adding full bibliography for 7126838--7126851.cif.'
_cod_original_cell_volume        2373.9(8)
_cod_original_formula_sum        'C14.93 H9.90 N O2'
_cod_database_code               7126843
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: C1S(0.2) C3S(0.1) C4S(0.2) C5S(0.1) C2S(0.1) C6S(0.1)
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_exptl_crystal_mounting_method Litholoop
_olex2_submission_special_instructions 'No special instructions were received'
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
O1 O 0.50689(7) 0.38182(7) 0.54831(12) 0.0308(3) Uani 1 1 d . . . . .
O2 O 0.40316(8) 0.22607(7) 0.12202(13) 0.0343(3) Uani 1 1 d . . . . .
N1 N 0.27689(10) 0.50912(10) 0.11335(17) 0.0388(4) Uani 1 1 d . . . . .
C1 C 0.45514(9) 0.33281(9) 0.28351(15) 0.0270(3) Uani 1 1 d . . . . .
C2 C 0.46459(9) 0.33635(9) 0.46690(16) 0.0269(3) Uani 1 1 d . . . . .
C3 C 0.41208(9) 0.27623(9) 0.52306(16) 0.0289(3) Uani 1 1 d . . . . .
C4 C 0.39479(10) 0.26229(10) 0.67739(17) 0.0316(3) Uani 1 1 d . . . . .
H4 H 0.415655 0.294179 0.762345 0.038 Uiso 1 1 calc R . . . .
C5 C 0.34587(11) 0.19994(11) 0.70201(18) 0.0366(4) Uani 1 1 d . . . . .
H5 H 0.333454 0.188801 0.806025 0.044 Uiso 1 1 calc R . . . .
C6 C 0.31463(12) 0.15342(11) 0.5774(2) 0.0394(4) Uani 1 1 d . . . . .
H6 H 0.281090 0.111345 0.597886 0.047 Uiso 1 1 calc R . . . .
C7 C 0.33174(11) 0.16754(10) 0.42305(19) 0.0358(4) Uani 1 1 d . . . . .
H7 H 0.310678 0.135774 0.338006 0.043 Uiso 1 1 calc R . . . .
C8 C 0.38064(10) 0.22968(9) 0.39843(17) 0.0299(3) Uani 1 1 d . . . . .
C9 C 0.41045(9) 0.25701(9) 0.25021(16) 0.0288(3) Uani 1 1 d . . . . .
C10 C 0.34502(11) 0.52113(10) 0.22196(19) 0.0360(4) Uani 1 1 d . . . . .
H10 H 0.354290 0.570096 0.261150 0.043 Uiso 1 1 calc R . . . .
C11 C 0.40304(10) 0.46675(10) 0.28114(17) 0.0318(3) Uani 1 1 d . . . . .
H11 H 0.448918 0.478188 0.361643 0.038 Uiso 1 1 calc R . . . .
C12 C 0.39313(9) 0.39506(9) 0.22090(16) 0.0283(3) Uani 1 1 d . . . . .
C13 C 0.32273(10) 0.38206(10) 0.10518(17) 0.0320(3) Uani 1 1 d . . . . .
H13 H 0.313357 0.334261 0.059717 0.038 Uiso 1 1 calc R . . . .
C14 C 0.26694(11) 0.43985(11) 0.05790(18) 0.0366(4) Uani 1 1 d . . . . .
H14 H 0.218655 0.429716 -0.018566 0.044 Uiso 1 1 calc R . . . .
C1S C 0.4819(8) 0.0571(9) 1.160(2) 0.068(5) Uani 0.2 1 d . . P . .
C3S C 0.4615(15) 0.0715(12) 1.036(4) 0.045(4) Uiso 0.1 1 d . . P A .
C4S C 0.4744(5) 0.0768(6) 0.9456(14) 0.040(2) Uani 0.2 1 d . . P A .
C5S C 0.4707(16) 0.0465(16) 0.955(3) 0.044(5) Uiso 0.1 1 d . . P A .
C2S C 0.4612(19) 0.0671(15) 1.117(4) 0.045(6) Uiso 0.1 1 d . . P A 1
C6S C 0.4668(16) -0.0211(15) 1.150(3) 0.059(6) Uani 0.1 1 d . . P A 2
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 0.0063 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0112 0.0059 '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
C10 N1 C14 116.30(15) . . ?
C2 C1 C1 112.68(14) . 2_655 ?
C9 C1 C1 109.47(8) . 2_655 ?
C9 C1 C2 101.91(11) . . ?
C12 C1 C1 115.04(10) . 2_655 ?
C12 C1 C2 107.32(12) . . ?
C12 C1 C9 109.59(12) . . ?
O1 C2 C1 125.44(13) . . ?
O1 C2 C3 126.64(13) . . ?
C3 C2 C1 107.91(12) . . ?
C4 C3 C2 128.06(14) . . ?
C8 C3 C2 110.79(12) . . ?
C8 C3 C4 121.12(14) . . ?
C3 C4 H4 121.3 . . ?
C5 C4 C3 117.41(15) . . ?
C5 C4 H4 121.3 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.39(14) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.14(16) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 121.3 . . ?
C8 C7 C6 117.50(15) . . ?
C8 C7 H7 121.3 . . ?
C3 C8 C9 109.23(13) . . ?
C7 C8 C3 121.44(14) . . ?
C7 C8 C9 129.31(14) . . ?
O2 C9 C1 124.12(13) . . ?
O2 C9 C8 127.22(16) . . ?
C8 C9 C1 108.65(12) . . ?
N1 C10 H10 117.9 . . ?
N1 C10 C11 124.25(17) . . ?
C11 C10 H10 117.9 . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 119.10(15) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C1 121.07(13) . . ?
C11 C12 C13 117.14(14) . . ?
C13 C12 C1 121.76(14) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.12(16) . . ?
C14 C13 H13 120.4 . . ?
N1 C14 C13 124.05(15) . . ?
N1 C14 H14 118.0 . . ?
C13 C14 H14 118.0 . . ?
C1S C1S C4S 159.5(12) 2_657 . ?
C1S C1S C5S 163.6(16) 2_657 . ?
C1S C1S C2S 7.3(11) 2_657 2_657 ?
C3S C1S C1S 165.8(15) . 2_657 ?
C3S C1S C4S 13.6(14) . . ?
C3S C1S C5S 23.1(16) . . ?
C3S C1S C2S 159.1(19) . 2_657 ?
C3S C1S C6S 98.5(19) . . ?
C4S C1S C2S 152.4(11) . 2_657 ?
C5S C1S C4S 17.5(8) . . ?
C5S C1S C2S 159.7(13) . 2_657 ?
C6S C1S C4S 97.9(15) . . ?
C6S C1S C5S 80.4(16) . . ?
C1S C3S C6S 47.4(15) . . ?
C4S C3S C1S 148(3) . . ?
C4S C3S C5S 39(2) . . ?
C4S C3S C6S 124(2) . . ?
C5S C3S C1S 127(3) . . ?
C5S C3S C6S 87(3) . . ?
C2S C3S C1S 19(3) . . ?
C2S C3S C4S 166(4) . . ?
C2S C3S C5S 140(5) . . ?
C3S C4S C1S 18.0(16) . . ?
C3S C4S C2S 6(2) . . ?
C3S C4S C6S 127(2) . 5_657 ?
C5S C4S C1S 70(3) . . ?
C5S C4S C3S 73(3) . . ?
C5S C4S C2S 74(3) . . ?
C5S C4S C6S 63(3) . 5_657 ?
C2S C4S C1S 12.2(11) . . ?
C2S C4S C6S 123.8(16) . 5_657 ?
C6S C4S C1S 113.4(13) 5_657 . ?
C1S C5S C5S 74.2(15) . 5_657 ?
C3S C5S C1S 30(2) . . ?
C3S C5S C5S 104(3) . 5_657 ?
C3S C5S C2S 18(2) . . ?
C3S C5S C6S 148(3) . 5_657 ?
C4S C5S C1S 92(3) . . ?
C4S C5S C3S 68(3) . . ?
C4S C5S C5S 145(4) . 5_657 ?
C4S C5S C2S 85(3) . . ?
C4S C5S C6S 97(4) . 5_657 ?
C2S C5S C1S 14.3(11) . . ?
C2S C5S C5S 87(2) . 5_657 ?
C2S C5S C6S 144(2) . 5_657 ?
C6S C5S C1S 130(2) 5_657 . ?
C3S C2S C1S 154(4) . 2_657 ?
C3S C2S C4S 7(2) . . ?
C3S C2S C5S 22(3) . . ?
C4S C2S C1S 146.2(18) . 2_657 ?
C5S C2S C1S 142(2) . 2_657 ?
C5S C2S C4S 21.6(11) . . ?
C1S C6S C3S 34.1(12) . . ?
C1S C6S C4S 122.6(16) . 5_657 ?
C1S C6S C5S 103.3(19) . 5_657 ?
C1S C6S C6S 82.9(15) . 2_657 ?
C4S C6S C3S 106.2(15) 5_657 . ?
C4S C6S C6S 99.8(17) 5_657 2_657 ?
C5S C6S C3S 87.7(19) 5_657 . ?
C5S C6S C4S 19.7(11) 5_657 5_657 ?
C5S C6S C6S 103(2) 5_657 2_657 ?
C6S C6S C3S 116.0(12) 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
O1 C2 1.2152(18) . ?
O2 C9 1.2184(18) . ?
N1 C10 1.337(2) . ?
N1 C14 1.340(3) . ?
C1 C1 1.571(3) 2_655 ?
C1 C2 1.5506(19) . ?
C1 C9 1.546(2) . ?
C1 C12 1.534(2) . ?
C2 C3 1.473(2) . ?
C3 C4 1.3949(18) . ?
C3 C8 1.394(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.395(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.386(2) . ?
C8 C9 1.480(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.394(2) . ?
C12 C13 1.401(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(2) . ?
C14 H14 0.9500 . ?
C1S C1S 1.57(4) 2_657 ?
C1S C3S 1.09(3) . ?
C1S C4S 1.85(2) . ?
C1S C5S 1.74(3) . ?
C1S C2S 2.00(4) 2_657 ?
C1S C6S 1.43(3) . ?
C3S C4S 0.83(3) . ?
C3S C5S 0.85(3) . ?
C3S C2S 0.69(3) . ?
C3S C6S 1.93(4) . ?
C4S C5S 0.56(2) . ?
C4S C2S 1.51(3) . ?
C4S C6S 1.64(3) 5_657 ?
C5S C5S 2.02(5) 5_657 ?
C5S C2S 1.45(4) . ?
C5S C6S 1.47(3) 5_657 ?
C6S C6S 1.89(6) 2_657 ?
