# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_exp_224
_database_code_depnum_ccdc_archive 'CCDC 2166741'
loop_
_audit_author_name
_audit_author_address
'Nobuyoshi morita'
;Showa Pharmaceutical University
Japan
;
_audit_update_record             
;
2022-04-16 deposited with the CCDC.	2022-07-15 downloaded from the CCDC.
;
_audit_creation_date             2022-04-16
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.73(C15 H19 N O)'
_chemical_formula_sum            'C11 H10 N O'
_chemical_formula_weight         172.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   7.3602(3)
_cell_length_b                   6.9650(3)
_cell_length_c                   50.466(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2587.09(19)
_cell_formula_units_Z            11
_cell_measurement_reflns_used    6223
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.9840
_cell_measurement_theta_min      6.2430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.63a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1001
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       63
_diffrn_reflns_limit_l_min       -62
_diffrn_reflns_number            8847
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.167
_diffrn_reflns_theta_min         5.259
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     78.00 111.00   0.50    0.05    --   48.95 125.00 150.00   66
  2  ω     93.00 173.00   0.50    0.12    --  107.74  11.00  56.00  160
  3  ω    -12.00  25.00   0.50    0.05    --   48.95 -19.00 -30.00   74
  4  ω     -1.00  25.00   0.50    0.05    --   48.95 -19.00 -90.00   52
  5  ω     76.00 101.00   0.50    0.05    --   48.95 125.00-180.00   50
  6  ω     -8.00  25.00   0.50    0.05    --   48.95 -19.00-180.00   66
  7  ω     45.00  70.00   0.50    0.12    --  107.74 -99.00 -30.00   50
  8  ω     70.00 108.00   0.50    0.12    --  107.74-117.00 122.00   76
  9  ω     36.00  66.00   0.50    0.12    --  107.74-117.00 122.00   60
 10  ω     73.00  98.00   0.50    0.12    --  107.74 -99.00 -30.00   50
 11  ω    -56.00 -30.00   0.50    0.12    --  -97.00  57.00-120.00   52
 12  ω    -95.00 -64.00   0.50    0.05    --  -48.95 140.00 -74.00   62
 13  ω    -65.00 -38.00   0.50    0.12    --  -97.00  57.00 150.00   54
 14  ω   -158.00 -76.00   0.50    0.12    --  -97.00-140.00-134.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-Custom'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0263528000
_diffrn_orient_matrix_UB_12      -0.0542773000
_diffrn_orient_matrix_UB_13      -0.0293474000
_diffrn_orient_matrix_UB_21      -0.0155455000
_diffrn_orient_matrix_UB_22      -0.2140787000
_diffrn_orient_matrix_UB_23      0.0072617000
_diffrn_orient_matrix_UB_31      -0.2071631000
_diffrn_orient_matrix_UB_32      0.0090599000
_diffrn_orient_matrix_UB_33      -0.0042597000
_diffrn_oxdiff_digest_frames     
;
01935ab971be8505fff41e794c66a12ef30006606b7
;
_diffrn_oxdiff_digest_hkl        
;
01c99b92f9f75763add5da5c9567723e6b55da
;
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2349
_reflns_number_total             2574
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.41.63a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.63a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.63a (Rigaku OD, 2020)'
_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         0.203
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2574
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0449
_refine_ls_restrained_S_all      1.096
_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)+(0.0544P)²+1.3792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1248
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00F(H00J)
2.b Secondary CH2 refined with riding coordinates:
 C008(H00A,H00B), C00B(H00D,H00E), C00E(H00H,H00I)
2.c Aromatic/amide H refined with riding coordinates:
 C003(H003), C006(H006), C009(H009), C00A(H00C), C00C(H00F), C00D(H00G)
2.d Idealised Me refined as rotating group:
 C00G(H00K,H00L,H00M), C00H(H00N,H00O,H00P)
;
_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
O001 O 0.54019(14) 0.47857(15) 0.68581(2) 0.0274(3) Uani 1 1 d . . . . .
N002 N 0.54207(16) 0.42192(18) 0.65896(2) 0.0243(3) Uani 1 1 d . . . . .
C003 C 0.53544(17) 0.3853(2) 0.60190(3) 0.0207(3) Uani 1 1 d . . . . .
H003 H 0.579496 0.285672 0.612347 0.025 Uiso 1 1 calc R . . . .
C004 C 0.49546(17) 0.5481(2) 0.61497(3) 0.0208(3) Uani 1 1 d . . . . .
C005 C 0.51971(18) 0.3422(2) 0.57362(3) 0.0212(3) Uani 1 1 d . . . . .
C006 C 0.40634(18) 0.4419(2) 0.55596(3) 0.0235(3) Uani 1 1 d . . . . .
H006 H 0.336325 0.543720 0.562110 0.028 Uiso 1 1 calc R . . . .
C007 C 0.50746(18) 0.5673(2) 0.64402(3) 0.0213(3) Uani 1 1 d . . . . .
C008 C 0.43445(19) 0.7398(2) 0.60431(3) 0.0225(3) Uani 1 1 d . . . . .
H00A H 0.304722 0.739861 0.600919 0.027 Uiso 1 1 calc R . . . .
H00B H 0.497841 0.770763 0.588004 0.027 Uiso 1 1 calc R . . . .
C009 C 0.61192(19) 0.1367(2) 0.53701(3) 0.0270(3) Uani 1 1 d . . . . .
H009 H 0.680829 0.034432 0.530735 0.032 Uiso 1 1 calc R . . . .
C00A C 0.61944(18) 0.1871(2) 0.56356(3) 0.0238(3) Uani 1 1 d . . . . .
H00C H 0.692519 0.116256 0.574973 0.029 Uiso 1 1 calc R . . . .
C00B C 0.48303(19) 0.8835(2) 0.62631(3) 0.0243(3) Uani 1 1 d . . . . .
H00D H 0.605672 0.931643 0.623979 0.029 Uiso 1 1 calc R . . . .
H00E H 0.399453 0.991194 0.626257 0.029 Uiso 1 1 calc R . . . .
C00C C 0.39773(19) 0.3902(2) 0.52951(3) 0.0264(3) Uani 1 1 d . . . . .
H00F H 0.321640 0.457550 0.518097 0.032 Uiso 1 1 calc R . . . .
C00D C 0.5012(2) 0.2393(2) 0.51980(3) 0.0277(3) Uani 1 1 d . . . . .
H00G H 0.496457 0.207125 0.501929 0.033 Uiso 1 1 calc R . . . .
C00E C 0.4670(2) 0.7699(2) 0.65208(3) 0.0265(3) Uani 1 1 d . . . . .
H00H H 0.554087 0.814988 0.665091 0.032 Uiso 1 1 calc R . . . .
H00I H 0.345655 0.780342 0.659425 0.032 Uiso 1 1 calc R . . . .
C00F C 0.5744(2) 0.3144(2) 0.70243(3) 0.0264(3) Uani 1 1 d . . . . .
H00J H 0.686102 0.250074 0.696685 0.032 Uiso 1 1 calc R . . . .
C00G C 0.4174(2) 0.1741(2) 0.70153(3) 0.0330(4) Uani 1 1 d . . . . .
H00K H 0.308408 0.237234 0.707326 0.050 Uiso 1 1 calc GR . . . .
H00L H 0.442671 0.067386 0.712986 0.050 Uiso 1 1 calc GR . . . .
H00M H 0.401399 0.128881 0.683717 0.050 Uiso 1 1 calc GR . . . .
C00H C 0.6013(2) 0.3982(3) 0.72981(3) 0.0355(4) Uani 1 1 d . . . . .
H00N H 0.701779 0.486150 0.729519 0.053 Uiso 1 1 calc GR . . . .
H00O H 0.626085 0.296747 0.742160 0.053 Uiso 1 1 calc GR . . . .
H00P H 0.493216 0.465086 0.735112 0.053 Uiso 1 1 calc GR . . . .


_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
O001 N002 1.4113(14) . ?
O001 C00F 1.4407(17) . ?
N002 C007 1.2880(19) . ?
C003 C004 1.344(2) . ?
C003 C005 1.4630(18) . ?
C004 C007 1.4749(19) . ?
C004 C008 1.5083(19) . ?
C005 C006 1.4046(19) . ?
C005 C00A 1.401(2) . ?
C006 C00C 1.384(2) . ?
C007 C00E 1.498(2) . ?
C008 C00B 1.537(2) . ?
C009 C00A 1.386(2) . ?
C009 C00D 1.389(2) . ?
C00B C00E 1.527(2) . ?
C00C C00D 1.388(2) . ?
C00F C00G 1.514(2) . ?
C00F C00H 1.513(2) . ?

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
N002 O001 C00F 109.60(10) . . ?
C007 N002 O001 109.89(12) . . ?
C004 C003 C005 129.39(13) . . ?
C003 C004 C007 123.46(13) . . ?
C003 C004 C008 129.56(12) . . ?
C007 C004 C008 106.98(11) . . ?
C006 C005 C003 124.35(13) . . ?
C00A C005 C003 118.07(12) . . ?
C00A C005 C006 117.55(13) . . ?
C00C C006 C005 120.71(13) . . ?
N002 C007 C004 121.48(13) . . ?
N002 C007 C00E 128.39(13) . . ?
C004 C007 C00E 110.09(12) . . ?
C004 C008 C00B 104.45(11) . . ?
C00A C009 C00D 119.83(14) . . ?
C009 C00A C005 121.65(13) . . ?
C00E C00B C008 105.05(11) . . ?
C006 C00C C00D 120.82(13) . . ?
C00C C00D C009 119.42(13) . . ?
C007 C00E C00B 103.99(11) . . ?
O001 C00F C00G 111.17(12) . . ?
O001 C00F C00H 104.36(12) . . ?
C00H C00F C00G 112.12(13) . . ?

_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 1.513
_oxdiff_exptl_absorpt_empirical_full_min 0.796
