# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_r20200716b
_database_code_depnum_ccdc_archive 'CCDC 2285492'
loop_
_audit_author_name
_audit_author_address
'Yumin Liu'
;Beijing Normal University
China
;
_audit_update_record             
;
2023-07-31 deposited with the CCDC.	2023-11-21 downloaded from the CCDC.
;
_audit_creation_date             2020-07-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 O2'
_chemical_formula_sum            'C15 H12 O2'
_chemical_formula_weight         224.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.6333(7)
_cell_length_b                   10.6401(7)
_cell_length_c                   24.273(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2229.7(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4595
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      32.6760
_cell_measurement_theta_min      2.8720
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0836
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            16650
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         1.678
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_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   -120.00  60.00   1.00    2.00    --  -30.00  45.00   0.00  180
  2  ω   -120.00  30.00   1.00    2.00    --  -30.00  45.00  90.00  150
  3  ω   -120.00   0.00   1.00    2.00    --  -30.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0150638000
_diffrn_orient_matrix_UB_12      0.0187134000
_diffrn_orient_matrix_UB_13      -0.0275195000
_diffrn_orient_matrix_UB_21      -0.0069001000
_diffrn_orient_matrix_UB_22      -0.0639550000
_diffrn_orient_matrix_UB_23      -0.0078622000
_diffrn_orient_matrix_UB_31      -0.0804563000
_diffrn_orient_matrix_UB_32      0.0020440000
_diffrn_orient_matrix_UB_33      0.0059120000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1782
_reflns_number_total             2281
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       CrystalClear(Rigaku,2008)
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.063
_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)+(0.0458P)²+1.0894P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1260
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C12(H12), C13(H13),
  C14(H14), C15(H15)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.70868(16) 0.69654(12) 0.63706(5) 0.0298(3) Uani 1 1 d . . . . .
H1 H 0.765411 0.724089 0.611671 0.045 Uiso 1 1 calc GR . . . .
O2 O 0.83914(15) 0.70796(11) 0.54769(5) 0.0293(3) Uani 1 1 d . . . . .
C1 C 0.4766(2) 0.61160(18) 0.70433(8) 0.0272(4) Uani 1 1 d . . . . .
H1A H 0.510014 0.696346 0.707580 0.033 Uiso 1 1 calc R . . . .
C2 C 0.3754(2) 0.56256(18) 0.74283(8) 0.0312(5) Uani 1 1 d . . . . .
H2 H 0.339282 0.613841 0.772178 0.037 Uiso 1 1 calc R . . . .
C3 C 0.3265(2) 0.43905(19) 0.73882(8) 0.0318(5) Uani 1 1 d . . . . .
H3 H 0.257392 0.405283 0.765450 0.038 Uiso 1 1 calc R . . . .
C4 C 0.3789(2) 0.36478(18) 0.69566(8) 0.0294(4) Uani 1 1 d . . . . .
H4 H 0.345910 0.279852 0.692857 0.035 Uiso 1 1 calc R . . . .
C5 C 0.4792(2) 0.41393(17) 0.65667(7) 0.0267(4) Uani 1 1 d . . . . .
H5 H 0.513528 0.362832 0.626981 0.032 Uiso 1 1 calc R . . . .
C6 C 0.5302(2) 0.53809(16) 0.66074(7) 0.0232(4) Uani 1 1 d . . . . .
C7 C 0.6383(2) 0.59371(16) 0.62035(8) 0.0237(4) Uani 1 1 d . . . . .
C8 C 0.6669(2) 0.54527(16) 0.56859(7) 0.0245(4) Uani 1 1 d . . . . .
H8 H 0.614748 0.471437 0.556771 0.029 Uiso 1 1 calc R . . . .
C9 C 0.7742(2) 0.60543(16) 0.53296(7) 0.0241(4) Uani 1 1 d . . . . .
C10 C 0.8152(2) 0.55387(16) 0.47821(7) 0.0233(4) Uani 1 1 d . . . . .
C11 C 0.7560(2) 0.43949(17) 0.45952(7) 0.0251(4) Uani 1 1 d . . . . .
H11 H 0.684717 0.394120 0.481736 0.030 Uiso 1 1 calc R . . . .
C12 C 0.8003(2) 0.39166(17) 0.40889(8) 0.0272(4) Uani 1 1 d . . . . .
H12 H 0.759961 0.313426 0.396626 0.033 Uiso 1 1 calc R . . . .
C13 C 0.9034(2) 0.45776(18) 0.37601(8) 0.0294(4) Uani 1 1 d . . . . .
H13 H 0.932504 0.425446 0.341028 0.035 Uiso 1 1 calc R . . . .
C14 C 0.9637(2) 0.57070(17) 0.39420(8) 0.0286(4) Uani 1 1 d . . . . .
H14 H 1.034852 0.615693 0.371766 0.034 Uiso 1 1 calc R . . . .
C15 C 0.9209(2) 0.61839(17) 0.44496(8) 0.0273(4) Uani 1 1 d . . . . .
H15 H 0.963691 0.695652 0.457346 0.033 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 H1 0.8400 . ?
O1 C7 1.316(2) . ?
O2 C9 1.278(2) . ?
C1 H1A 0.9500 . ?
C1 C2 1.381(3) . ?
C1 C6 1.395(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.396(2) . ?
C6 C7 1.477(3) . ?
C7 C8 1.380(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.419(3) . ?
C9 C10 1.481(3) . ?
C10 C11 1.396(2) . ?
C10 C15 1.398(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(3) . ?
C15 H15 0.9500 . ?

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
C7 O1 H1 109.5 . . ?
C2 C1 H1A 119.6 . . ?
C2 C1 C6 120.74(18) . . ?
C6 C1 H1A 119.6 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.28(18) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.60(18) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.31(18) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.39(17) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.67(17) . . ?
C1 C6 C7 119.24(16) . . ?
C5 C6 C7 122.09(16) . . ?
O1 C7 C6 114.86(16) . . ?
O1 C7 C8 120.54(17) . . ?
C8 C7 C6 124.60(16) . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.22(16) . . ?
C9 C8 H8 119.9 . . ?
O2 C9 C8 120.05(16) . . ?
O2 C9 C10 117.54(16) . . ?
C8 C9 C10 122.41(16) . . ?
C11 C10 C9 121.79(16) . . ?
C11 C10 C15 118.66(17) . . ?
C15 C10 C9 119.49(16) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.53(17) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.11(17) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 119.94(18) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.19(18) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.57(18) . . ?
C14 C15 H15 119.7 . . ?

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 C7 C8 C9 0.6(3) . . . . ?
O2 C9 C10 C11 176.97(16) . . . . ?
O2 C9 C10 C15 -0.4(2) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C1 C6 C7 O1 18.2(2) . . . . ?
C1 C6 C7 C8 -161.70(17) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
C2 C1 C6 C7 179.98(16) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C4 C5 C6 C7 179.41(17) . . . . ?
C5 C6 C7 O1 -162.01(16) . . . . ?
C5 C6 C7 C8 18.1(3) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C6 C7 C8 C9 -179.48(16) . . . . ?
C7 C8 C9 O2 -3.3(3) . . . . ?
C7 C8 C9 C10 176.77(16) . . . . ?
C8 C9 C10 C11 -3.1(3) . . . . ?
C8 C9 C10 C15 179.52(16) . . . . ?
C9 C10 C11 C12 -177.94(16) . . . . ?
C9 C10 C15 C14 178.55(16) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C11 C10 C15 C14 1.1(3) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C13 C14 C15 C10 -0.6(3) . . . . ?
C15 C10 C11 C12 -0.5(3) . . . . ?

_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 1.414
_oxdiff_exptl_absorpt_empirical_full_min 0.568
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_r20200716a
_database_code_depnum_ccdc_archive 'CCDC 2285493'
loop_
_audit_author_name
_audit_author_address
'Yumin Liu'
;Beijing Normal University
China
;
_audit_update_record             
;
2023-07-31 deposited with the CCDC.	2023-11-21 downloaded from the CCDC.
;
_audit_creation_date             2020-07-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 O2'
_chemical_formula_sum            'C15 H12 O2'
_chemical_formula_weight         224.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   12.5547(8)
_cell_length_b                   11.7675(6)
_cell_length_c                   7.7848(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.444(7)
_cell_angle_gamma                90
_cell_volume                     1118.59(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5397
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      32.6770
_cell_measurement_theta_min      3.1550
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11617
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.199
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    3.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00    3.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00    3.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0519552000
_diffrn_orient_matrix_UB_12      0.0211416000
_diffrn_orient_matrix_UB_13      -0.0448905000
_diffrn_orient_matrix_UB_21      0.0018739000
_diffrn_orient_matrix_UB_22      0.0404928000
_diffrn_orient_matrix_UB_23      0.0681667000
_diffrn_orient_matrix_UB_31      0.0259505000
_diffrn_orient_matrix_UB_32      0.0393301000
_diffrn_orient_matrix_UB_33      -0.0459434000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1836
_reflns_number_total             2276
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       CrystalClear(Rigaku,2008)
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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)'
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0474
_refine_ls_restrained_S_all      1.044
_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)+(0.0543P)²+0.4038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1232
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C12(H12), C13(H13),
  C14(H14), C15(H15)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.58570(9) 0.90420(9) 0.35967(17) 0.0347(3) Uani 1 1 d . . . . .
H1 H 0.645984 0.917282 0.334198 0.052 Uiso 1 1 calc GR . . . .
O2 O 0.76146(9) 0.86971(8) 0.28266(15) 0.0323(3) Uani 1 1 d . . . . .
C1 C 0.39384(13) 0.84078(13) 0.4376(2) 0.0293(4) Uani 1 1 d . . . . .
H1A H 0.412979 0.918880 0.437482 0.035 Uiso 1 1 calc R . . . .
C2 C 0.29531(13) 0.80928(14) 0.4752(2) 0.0332(4) Uani 1 1 d . . . . .
H2 H 0.247412 0.865716 0.501605 0.040 Uiso 1 1 calc R . . . .
C3 C 0.26669(13) 0.69571(14) 0.4743(2) 0.0325(4) Uani 1 1 d . . . . .
H3 H 0.199030 0.674154 0.499638 0.039 Uiso 1 1 calc R . . . .
C4 C 0.33666(13) 0.61367(13) 0.4366(2) 0.0320(4) Uani 1 1 d . . . . .
H4 H 0.317018 0.535684 0.436001 0.038 Uiso 1 1 calc R . . . .
C5 C 0.43516(13) 0.64478(13) 0.3996(2) 0.0287(4) Uani 1 1 d . . . . .
H5 H 0.482889 0.587979 0.373727 0.034 Uiso 1 1 calc R . . . .
C6 C 0.46484(12) 0.75869(12) 0.40005(19) 0.0239(3) Uani 1 1 d . . . . .
C7 C 0.56926(12) 0.79548(12) 0.35971(19) 0.0244(3) Uani 1 1 d . . . . .
C8 C 0.64736(12) 0.72063(12) 0.32439(19) 0.0243(3) Uani 1 1 d . . . . .
H8 H 0.634702 0.641053 0.324937 0.029 Uiso 1 1 calc R . . . .
C9 C 0.74430(12) 0.76177(12) 0.28811(19) 0.0246(3) Uani 1 1 d . . . . .
C10 C 0.83221(12) 0.68601(12) 0.25575(19) 0.0245(3) Uani 1 1 d . . . . .
C11 C 0.83265(14) 0.57008(14) 0.2876(3) 0.0395(4) Uani 1 1 d . . . . .
H11 H 0.773388 0.536206 0.325584 0.047 Uiso 1 1 calc R . . . .
C12 C 0.91887(15) 0.50361(15) 0.2642(3) 0.0454(5) Uani 1 1 d . . . . .
H12 H 0.918733 0.424383 0.287611 0.055 Uiso 1 1 calc R . . . .
C13 C 1.00527(13) 0.55099(14) 0.2073(2) 0.0343(4) Uani 1 1 d . . . . .
H13 H 1.064797 0.505057 0.192867 0.041 Uiso 1 1 calc R . . . .
C14 C 1.00398(13) 0.66585(14) 0.1717(2) 0.0340(4) Uani 1 1 d . . . . .
H14 H 1.062182 0.698996 0.129939 0.041 Uiso 1 1 calc R . . . .
C15 C 0.91846(13) 0.73303(13) 0.1966(2) 0.0301(4) Uani 1 1 d . . . . .
H15 H 0.918791 0.812204 0.172873 0.036 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 H1 0.8400 . ?
O1 C7 1.2959(17) . ?
O2 C9 1.2907(17) . ?
C1 H1A 0.9500 . ?
C1 C2 1.386(2) . ?
C1 C6 1.391(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(2) . ?
C6 C7 1.482(2) . ?
C7 C8 1.392(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.398(2) . ?
C9 C10 1.485(2) . ?
C10 C11 1.386(2) . ?
C10 C15 1.387(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.379(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(2) . ?
C15 H15 0.9500 . ?

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
C7 O1 H1 109.5 . . ?
C2 C1 H1A 119.8 . . ?
C2 C1 C6 120.37(15) . . ?
C6 C1 H1A 119.8 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.06(15) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.90(15) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.19(15) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.44(15) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.04(14) . . ?
C1 C6 C7 118.91(13) . . ?
C5 C6 C7 122.04(13) . . ?
O1 C7 C6 115.93(13) . . ?
O1 C7 C8 120.33(14) . . ?
C8 C7 C6 123.74(13) . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.46(13) . . ?
C9 C8 H8 119.8 . . ?
O2 C9 C8 120.47(14) . . ?
O2 C9 C10 116.67(13) . . ?
C8 C9 C10 122.86(13) . . ?
C11 C10 C9 122.18(14) . . ?
C11 C10 C15 118.76(14) . . ?
C15 C10 C9 119.04(13) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.29(16) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.77(16) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.13(15) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.36(15) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.67(14) . . ?
C14 C15 H15 119.7 . . ?

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 C7 C8 C9 -0.1(2) . . . . ?
O2 C9 C10 C11 168.64(15) . . . . ?
O2 C9 C10 C15 -9.5(2) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C1 C6 C7 O1 -1.2(2) . . . . ?
C1 C6 C7 C8 178.45(14) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
C2 C1 C6 C7 179.75(14) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C4 C5 C6 C1 -0.2(2) . . . . ?
C4 C5 C6 C7 -179.50(14) . . . . ?
C5 C6 C7 O1 178.12(14) . . . . ?
C5 C6 C7 C8 -2.3(2) . . . . ?
C6 C1 C2 C3 -0.5(2) . . . . ?
C6 C7 C8 C9 -179.73(13) . . . . ?
C7 C8 C9 O2 -1.7(2) . . . . ?
C7 C8 C9 C10 177.78(13) . . . . ?
C8 C9 C10 C11 -10.9(2) . . . . ?
C8 C9 C10 C15 171.05(14) . . . . ?
C9 C10 C11 C12 -176.69(17) . . . . ?
C9 C10 C15 C14 177.41(14) . . . . ?
C10 C11 C12 C13 -0.7(3) . . . . ?
C11 C10 C15 C14 -0.8(2) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C12 C13 C14 C15 1.4(3) . . . . ?
C13 C14 C15 C10 -0.7(2) . . . . ?
C15 C10 C11 C12 1.4(3) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.680
_oxdiff_exptl_absorpt_empirical_full_min 0.694
