#------------------------------------------------------------------------------
#$Date: 2020-09-06 11:39:25 +0300 (Sun, 06 Sep 2020) $
#$Revision: 256033 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/68/7126842.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_7126842
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         'C0.46 Cl0.46, C14 H8 N O2'
_chemical_formula_sum            'C14.46 H8.9 Cl0.46 N O2'
_chemical_formula_weight         245.13
_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             2018-12-19
_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                 97.36(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.442(3)
_cell_length_b                   18.010(4)
_cell_length_c                   8.5151(17)
_cell_measurement_reflns_used    24158
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.528
_cell_measurement_theta_min      2.227
_cell_volume                     2348.6(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 0.993
_diffrn_measured_fraction_theta_max 0.995
_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  0.0310
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            23765
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         29.528
_diffrn_reflns_theta_min         2.227
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             1013
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.933
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3417
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0617
_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)+(0.1289P)²+2.5802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1915
_refine_ls_wR_factor_ref         0.1964
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3044
_reflns_number_total             3417
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc03408h2.cif
_cod_data_source_block           1a-DCE
_cod_depositor_comments
'Adding full bibliography for 7126838--7126851.cif.'
_cod_original_cell_volume        2348.6(8)
_cod_original_formula_sum        'C14.46 H8.90 Cl0.46 N O2'
_cod_database_code               7126842
_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. Restrained distances
 C1S-C2S
 1.55 with sigma of 0.02
3. Others
 Sof(C1S)=Sof(C2S)=0.5*FVAR(2)
 Sof(Cl1S)=FVAR(1)
4.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'
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
Cl1S Cl 0.9769(10) 0.5280(6) 1.1824(15) 0.356(10) Uiso 0.464(10) 1 d . . P . .
C1S C 0.9659(10) 0.5714(8) 1.0540(17) 0.066(4) Uiso 0.232(5) 1 d D . P . .
C2S C 0.9773(15) 0.5277(12) 0.921(2) 0.100(6) Uiso 0.232(5) 1 d D . P . .
O1 O 0.59743(8) 0.77626(6) 0.87621(12) 0.0202(3) Uani 1 1 d . . . . .
O2 O 0.49334(7) 0.61744(5) 0.45324(12) 0.0174(2) Uani 1 1 d . . . . .
N1 N 0.72659(10) 0.49325(8) 0.89215(17) 0.0261(3) Uani 1 1 d . . . . .
C1 C 0.54508(9) 0.66826(7) 0.71669(15) 0.0130(3) Uani 1 1 d . . . . .
C2 C 0.58975(9) 0.74485(7) 0.74870(16) 0.0146(3) Uani 1 1 d . . . . .
C3 C 0.61852(9) 0.77164(7) 0.60009(16) 0.0154(3) Uani 1 1 d . . . . .
C4 C 0.66617(10) 0.83502(8) 0.57337(18) 0.0203(3) Uani 1 1 d . . . . .
H4 H 0.686379 0.867010 0.655719 0.024 Uiso 1 1 calc R . . . .
C5 C 0.68250(11) 0.84881(9) 0.41886(19) 0.0235(3) Uani 1 1 d . . . . .
H5 H 0.714123 0.890781 0.397677 0.028 Uiso 1 1 calc R . . . .
C6 C 0.65209(10) 0.80051(9) 0.29469(17) 0.0216(3) Uani 1 1 d . . . . .
H6 H 0.663859 0.811005 0.192599 0.026 Uiso 1 1 calc R . . . .
C7 C 0.60461(9) 0.73717(8) 0.32181(16) 0.0172(3) Uani 1 1 d . . . . .
H7 H 0.584865 0.704800 0.239886 0.021 Uiso 1 1 calc R . . . .
C8 C 0.58777(9) 0.72404(7) 0.47600(16) 0.0144(3) Uani 1 1 d . . . . .
C9 C 0.53551(9) 0.66364(7) 0.53358(15) 0.0134(3) Uani 1 1 d . . . . .
C10 C 0.65787(11) 0.48032(8) 0.78262(19) 0.0229(3) Uani 1 1 d . . . . .
H10 H 0.649331 0.432086 0.744774 0.028 Uiso 1 1 calc R . . . .
C11 C 0.59852(10) 0.53438(8) 0.72196(17) 0.0183(3) Uani 1 1 d . . . . .
H11 H 0.553197 0.522701 0.643063 0.022 Uiso 1 1 calc R . . . .
C12 C 0.60820(9) 0.60648(7) 0.78163(16) 0.0144(3) Uani 1 1 d . . . . .
C13 C 0.67870(10) 0.61997(8) 0.89770(17) 0.0183(3) Uani 1 1 d . . . . .
H13 H 0.687382 0.667038 0.941833 0.022 Uiso 1 1 calc R . . . .
C14 C 0.73580(10) 0.56254(9) 0.94680(19) 0.0237(3) Uani 1 1 d . . . . .
H14 H 0.783270 0.573030 1.022247 0.028 Uiso 1 1 calc R . . . .
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'
Cl Cl 0.1453 0.1556 '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
Cl1S Cl1S C1S 137.4(13) 2_757 . ?
Cl1S Cl1S C2S 105.4(15) 2_757 5_767 ?
Cl1S Cl1S C2S 146(2) 2_757 . ?
C1S Cl1S C2S 86.3(14) . 5_767 ?
C1S Cl1S C2S 36.9(8) . . ?
C2S Cl1S C2S 51.5(15) 5_767 . ?
Cl1S C1S C2S 108.5(15) . . ?
Cl1S C1S C2S 51.6(10) . 5_767 ?
C2S C1S C2S 59.3(15) . 5_767 ?
Cl1S C2S Cl1S 128.5(15) 5_767 . ?
Cl1S C2S C1S 42.1(8) 5_767 5_767 ?
Cl1S C2S C2S 84.3(16) 5_767 5_767 ?
C1S C2S Cl1S 34.6(9) . . ?
C1S C2S Cl1S 87.2(10) 5_767 . ?
C1S C2S Cl1S 157(2) . 5_767 ?
C1S C2S C1S 120.7(15) . 5_767 ?
C1S C2S C2S 77.0(14) . 5_767 ?
C2S C2S Cl1S 44.2(9) 5_767 . ?
C2S C2S C1S 43.7(9) 5_767 5_767 ?
C14 N1 C10 116.44(13) . . ?
C2 C1 C1 109.37(8) . 2_656 ?
C9 C1 C1 112.90(13) . 2_656 ?
C9 C1 C2 101.98(10) . . ?
C12 C1 C1 114.93(9) . 2_656 ?
C12 C1 C2 109.51(11) . . ?
C12 C1 C9 107.33(10) . . ?
O1 C2 C1 124.11(12) . . ?
O1 C2 C3 127.44(13) . . ?
C3 C2 C1 108.44(11) . . ?
C4 C3 C2 129.20(13) . . ?
C4 C3 C8 121.02(13) . . ?
C8 C3 C2 109.74(11) . . ?
C3 C4 C5 117.63(13) . . ?
C4 C5 C6 121.17(13) . . ?
C7 C6 C5 121.06(13) . . ?
C8 C7 C6 117.53(13) . . ?
C3 C8 C9 110.42(11) . . ?
C7 C8 C3 121.57(12) . . ?
C7 C8 C9 127.98(12) . . ?
O2 C9 C1 125.42(12) . . ?
O2 C9 C8 126.56(12) . . ?
C8 C9 C1 108.01(11) . . ?
N1 C10 C11 124.20(14) . . ?
C10 C11 C12 118.79(14) . . ?
C11 C12 C1 120.66(12) . . ?
C13 C12 C1 122.07(12) . . ?
C13 C12 C11 117.24(13) . . ?
C14 C13 C12 119.44(14) . . ?
N1 C14 C13 123.85(15) . . ?
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
Cl1S Cl1S 1.27(2) 2_757 ?
Cl1S C1S 1.336(17) . ?
Cl1S C2S 2.23(2) . ?
Cl1S C2S 1.56(2) 5_767 ?
C1S C2S 1.410(16) . ?
C1S C2S 1.99(3) 5_767 ?
C2S C2S 1.75(5) 5_767 ?
O1 C2 1.2164(17) . ?
O2 C9 1.2125(16) . ?
N1 C10 1.340(2) . ?
N1 C14 1.333(2) . ?
C1 C1 1.569(3) 2_656 ?
C1 C2 1.5507(18) . ?
C1 C9 1.5495(18) . ?
C1 C12 1.5349(18) . ?
C2 C3 1.4750(19) . ?
C3 C4 1.3925(19) . ?
C3 C8 1.3959(18) . ?
C4 C5 1.393(2) . ?
C5 C6 1.403(2) . ?
C6 C7 1.3914(19) . ?
C7 C8 1.3910(18) . ?
C8 C9 1.4752(18) . ?
C10 C11 1.390(2) . ?
C11 C12 1.3954(19) . ?
C12 C13 1.395(2) . ?
C13 C14 1.388(2) . ?
