# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_123
_database_code_depnum_ccdc_archive 'CCDC 2031280'
loop_
_audit_author_name
_audit_author_address
indoles
;Heilongjiang University
China
;
_audit_update_record             
;
2020-09-10 deposited with the CCDC.	2021-01-07 downloaded from the CCDC.
;
_audit_creation_date             2017-07-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 N O3'
_chemical_formula_sum            'C18 H15 N O3'
_chemical_formula_weight         293.31
_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 0.0033 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'

_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 21/c'
_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                   5.974(5)
_cell_length_b                   16.697(5)
_cell_length_c                   14.741(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 91.617(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1469.8(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1479
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5130
_cell_measurement_theta_min      3.4050
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5306
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.411
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  MoKα
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1957
_reflns_number_total             2576
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    ?
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2576
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0650
_refine_ls_restrained_S_all      1.084
_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)+(0.0633P)²+1.1441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1609
_refine_ls_wR_factor_ref         0.1724
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C8(H8), C12(H12), C13(H13), C15(H15), C16(H16), N1(H1)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C 0.2359(5) 0.14377(18) 0.0445(2) 0.0454(7) Uani 1 1 d . . . . .
C2 C 0.0585(5) 0.1098(2) 0.0895(2) 0.0586(9) Uani 1 1 d . . . . .
H2 H -0.040238 0.076673 0.057272 0.070 Uiso 1 1 calc R . . . .
C3 C 0.0230(6) 0.1235(2) 0.1808(3) 0.0695(10) Uani 1 1 d . . . . .
H3 H -0.100789 0.100866 0.207815 0.083 Uiso 1 1 calc R . . . .
C4 C 0.1678(6) 0.1699(2) 0.2316(2) 0.0673(10) Uani 1 1 d . . . . .
H4 H 0.147705 0.177869 0.293240 0.081 Uiso 1 1 calc R . . . .
C5 C 0.3444(5) 0.20434(19) 0.18789(19) 0.0505(8) Uani 1 1 d . . . . .
C6 C 0.3787(5) 0.19597(17) 0.09395(17) 0.0416(7) Uani 1 1 d . . . . .
C7 C 0.5695(5) 0.24620(17) 0.07480(18) 0.0425(7) Uani 1 1 d . . . . .
C8 C 0.6436(6) 0.27696(19) 0.1572(2) 0.0552(8) Uani 1 1 d . . . . .
H8 H 0.768027 0.309869 0.165606 0.066 Uiso 1 1 calc R . . . .
C9 C 0.6593(5) 0.27070(18) -0.0110(2) 0.0499(8) Uani 1 1 d . . . . .
C10 C 0.8737(6) 0.3166(2) -0.0124(3) 0.0712(10) Uani 1 1 d . . . . .
H10A H 0.896117 0.344242 0.044227 0.107 Uiso 1 1 calc GR . . . .
H10B H 0.866922 0.354808 -0.061115 0.107 Uiso 1 1 calc GR . . . .
H10C H 0.995831 0.280358 -0.021281 0.107 Uiso 1 1 calc GR . . . .
C11 C 0.2825(5) 0.11627(17) -0.0494(2) 0.0440(7) Uani 1 1 d . . . . .
C12 C 0.4889(5) 0.08312(19) -0.0668(2) 0.0510(8) Uani 1 1 d . . . . .
H12 H 0.598614 0.081748 -0.020756 0.061 Uiso 1 1 calc R . . . .
C13 C 0.5359(5) 0.05213(19) -0.1505(2) 0.0507(8) Uani 1 1 d . . . . .
H13 H 0.675502 0.029599 -0.160415 0.061 Uiso 1 1 calc R . . . .
C14 C 0.3759(5) 0.05444(17) -0.21994(19) 0.0436(7) Uani 1 1 d . . . . .
C17 C 0.4233(5) 0.02247(19) -0.3115(2) 0.0521(8) Uani 1 1 d . . . . .
C15 C 0.1674(5) 0.0860(2) -0.2026(2) 0.0537(8) Uani 1 1 d . . . . .
H15 H 0.057077 0.086487 -0.248399 0.064 Uiso 1 1 calc R . . . .
C16 C 0.1207(5) 0.11672(19) -0.1184(2) 0.0509(8) Uani 1 1 d . . . . .
H16 H -0.020228 0.137862 -0.107963 0.061 Uiso 1 1 calc R . . . .
C18 C 0.7078(6) -0.0244(2) -0.4054(2) 0.0697(10) Uani 1 1 d . . . . .
H18A H 0.665580 0.010759 -0.454414 0.104 Uiso 1 1 calc GR . . . .
H18B H 0.636083 -0.075396 -0.414207 0.104 Uiso 1 1 calc GR . . . .
H18C H 0.867341 -0.031499 -0.403750 0.104 Uiso 1 1 calc GR . . . .
N1 N 0.5107(5) 0.25268(17) 0.22326(16) 0.0616(8) Uani 1 1 d . . . . .
H1 H 0.527013 0.265463 0.279572 0.074 Uiso 1 1 calc R . . . .
O1 O 0.5600(5) 0.25585(15) -0.08258(14) 0.0752(8) Uani 1 1 d . . . . .
O2 O 0.6397(4) 0.00969(14) -0.32124(14) 0.0592(6) Uani 1 1 d . . . . .
O3 O 0.2853(4) 0.0108(2) -0.36945(17) 0.0919(10) Uani 1 1 d . . . . .


_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
C1 C2 1.387(4) . ?
C1 C6 1.408(4) . ?
C1 C11 1.492(4) . ?
C2 C3 1.387(5) . ?
C3 C4 1.368(5) . ?
C4 C5 1.377(5) . ?
C5 C6 1.412(4) . ?
C5 N1 1.371(4) . ?
C6 C7 1.449(4) . ?
C7 C8 1.380(4) . ?
C7 C9 1.447(4) . ?
C8 N1 1.336(4) . ?
C9 C10 1.493(5) . ?
C9 O1 1.221(4) . ?
C11 C12 1.382(4) . ?
C11 C16 1.384(4) . ?
C12 C13 1.375(4) . ?
C13 C14 1.381(4) . ?
C14 C17 1.486(4) . ?
C14 C15 1.383(4) . ?
C17 O2 1.322(4) . ?
C17 O3 1.186(4) . ?
C15 C16 1.379(4) . ?
C18 O2 1.434(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 C6 117.7(3) . . ?
C2 C1 C11 118.9(3) . . ?
C6 C1 C11 123.0(3) . . ?
C1 C2 C3 122.5(3) . . ?
C4 C3 C2 120.8(3) . . ?
C3 C4 C5 117.5(3) . . ?
C4 C5 C6 123.5(3) . . ?
N1 C5 C4 128.6(3) . . ?
N1 C5 C6 107.9(3) . . ?
C1 C6 C5 117.8(3) . . ?
C1 C6 C7 136.5(2) . . ?
C5 C6 C7 105.7(3) . . ?
C8 C7 C6 106.1(3) . . ?
C8 C7 C9 123.2(3) . . ?
C9 C7 C6 130.3(3) . . ?
N1 C8 C7 110.3(3) . . ?
C7 C9 C10 119.8(3) . . ?
O1 C9 C7 121.0(3) . . ?
O1 C9 C10 119.2(3) . . ?
C12 C11 C1 119.1(3) . . ?
C12 C11 C16 118.3(3) . . ?
C16 C11 C1 122.4(3) . . ?
C13 C12 C11 121.6(3) . . ?
C12 C13 C14 120.0(3) . . ?
C13 C14 C17 121.2(3) . . ?
C13 C14 C15 118.8(3) . . ?
C15 C14 C17 120.0(3) . . ?
O2 C17 C14 111.6(2) . . ?
O3 C17 C14 124.5(3) . . ?
O3 C17 O2 123.9(3) . . ?
C16 C15 C14 120.9(3) . . ?
C15 C16 C11 120.4(3) . . ?
C8 N1 C5 109.9(2) . . ?
C17 O2 C18 117.4(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_20170803agh
_database_code_depnum_ccdc_archive 'CCDC 2031282'
loop_
_audit_author_name
_audit_author_address
INDOLES
;Heilongjiang University
China
;
_audit_update_record             
;
2020-09-10 deposited with the CCDC.	2021-01-07 downloaded from the CCDC.
;
_audit_creation_date             2017-08-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.67(C18 H15 N O3)'
_chemical_formula_sum            'C12 H10 N0.67 O2'
_chemical_formula_weight         195.54
_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 0.0033 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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1516(8)
_cell_length_b                   8.1871(8)
_cell_length_c                   11.8093(11)
_cell_angle_alpha                96.901(8)
_cell_angle_beta                 107.557(9)
_cell_angle_gamma                92.751(8)
_cell_volume                     743.02(13)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    1512
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.6755
_cell_measurement_theta_min      3.3060
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4629
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.313
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1954
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   46.00   80.00   1.0000    5.3100
omega____ theta____ kappa____ phi______ frames
    -       25.5830  178.0000 -150.0000 34

#__ type_ start__ end____ width___ exp.time_
  2 omega  -24.00   55.00   1.0000    5.3100
omega____ theta____ kappa____ phi______ frames
    -       25.5830  -99.0000   60.0000 79

#__ type_ start__ end____ width___ exp.time_
  3 omega   75.00  102.00   1.0000    5.3100
omega____ theta____ kappa____ phi______ frames
    -       25.5830   38.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega -100.00   -8.00   1.0000    5.3100
omega____ theta____ kappa____ phi______ frames
    -      -26.8330  -57.0000 -180.0000 92

#__ type_ start__ end____ width___ exp.time_
  5 omega    9.00   48.00   1.0000    5.3100
omega____ theta____ kappa____ phi______ frames
    -      -26.8330   77.0000   60.0000 39

#__ type_ start__ end____ width___ exp.time_
  6 omega  -25.00   20.00   1.0000    5.3100
omega____ theta____ kappa____ phi______ frames
    -      -26.8330  -99.0000  120.0000 45

#__ type_ start__ end____ width___ exp.time_
  7 omega  -56.00   37.00   1.0000    5.3100
omega____ theta____ kappa____ phi______ frames
    -      -26.8330   57.0000  -30.0000 93

#__ type_ start__ end____ width___ exp.time_
  8 omega  -12.00   13.00   1.0000    5.3100
omega____ theta____ kappa____ phi______ frames
    -      -26.8330  -99.0000  -60.0000 25
;
_diffrn_measurement_device_type  MoKα
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0172126000
_diffrn_orient_matrix_UB_12      -0.0530386000
_diffrn_orient_matrix_UB_13      0.0446971000
_diffrn_orient_matrix_UB_21      -0.0143982000
_diffrn_orient_matrix_UB_22      -0.0693795000
_diffrn_orient_matrix_UB_23      -0.0450836000
_diffrn_orient_matrix_UB_31      0.0888375000
_diffrn_orient_matrix_UB_32      0.0070745000
_diffrn_orient_matrix_UB_33      0.0043806000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2012
_reflns_number_total             2615
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.702
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2615
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      0.702
_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)+(0.1310P)²+0.4060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1532
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C8(H8), C13(H13), C16(H16), C18(H18), C19(H19),
 C20(H20)
2.b Idealised Me refined as rotating group:
 C0AA(H0AA,H0AB,H0AC), C1AA(H1AA,H1AB,H1AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
N1 N 0.20093(19) 0.98342(19) 0.92625(14) 0.0457(4) Uani 1 1 d . . . . .
H1 H 0.128764 1.035468 0.953793 0.055 Uiso 1 1 calc R . . . .
C2 C 0.6013(2) 0.8201(2) 0.72202(16) 0.0428(4) Uani 1 1 d . . . . .
C3 C 0.8016(2) 0.5797(2) 0.65796(16) 0.0441(5) Uani 1 1 d . . . . .
C4 C 0.4936(2) 0.9479(2) 0.75387(17) 0.0450(5) Uani 1 1 d . . . . .
C5 C 0.7746(2) 0.8588(3) 0.73444(18) 0.0509(5) Uani 1 1 d . . . . .
H5 H 0.824129 0.966300 0.763645 0.061 Uiso 1 1 calc R . . . .
C6 C 0.5298(3) 0.6591(2) 0.67665(18) 0.0477(5) Uani 1 1 d . . . . .
H6 H 0.414479 0.630782 0.668230 0.057 Uiso 1 1 calc R . . . .
C7 C 0.2841(2) 1.0404(2) 0.85316(17) 0.0436(4) Uani 1 1 d . . . . .
C8 C 0.6284(3) 0.5410(2) 0.64403(18) 0.0481(5) Uani 1 1 d . . . . .
H8 H 0.578308 0.434293 0.612355 0.058 Uiso 1 1 calc R . . . .
O9 O 0.8197(2) 0.31036(19) 0.57475(15) 0.0664(5) Uani 1 1 d . . . . .
O10 O 0.05975(19) 0.79026(18) 1.05871(14) 0.0612(4) Uani 1 1 d . . . . .
C11 C 0.1740(2) 0.7363(2) 1.02097(17) 0.0474(5) Uani 1 1 d . . . . .
C12 C 0.3908(2) 0.9186(2) 0.82825(17) 0.0423(4) Uani 1 1 d . . . . .
C13 C 0.8736(2) 0.7396(3) 0.70391(18) 0.0515(5) Uani 1 1 d . . . . .
H13 H 0.989780 0.766886 0.714264 0.062 Uiso 1 1 calc R . . . .
C14 C 0.2502(2) 0.8293(2) 0.94938(16) 0.0427(4) Uani 1 1 d . . . . .
C15 C 0.9117(3) 0.4546(3) 0.62526(18) 0.0521(5) Uani 1 1 d . . . . .
C16 C 0.3679(2) 0.7874(2) 0.89129(16) 0.0430(4) Uani 1 1 d . . . . .
H16 H 0.422691 0.690264 0.893024 0.052 Uiso 1 1 calc R . . . .
O17 O 1.0640(2) 0.4781(2) 0.64195(17) 0.0762(5) Uani 1 1 d . . . . .
C18 C 0.2741(3) 1.1877(2) 0.8049(2) 0.0548(5) Uani 1 1 d . . . . .
H18 H 0.201164 1.265488 0.820155 0.066 Uiso 1 1 calc R . . . .
C19 C 0.4845(3) 1.0962(3) 0.7094(2) 0.0576(6) Uani 1 1 d . . . . .
H19 H 0.552375 1.119244 0.661593 0.069 Uiso 1 1 calc R . . . .
C20 C 0.3752(3) 1.2137(3) 0.7342(2) 0.0618(6) Uani 1 1 d . . . . .
H20 H 0.371826 1.311884 0.701586 0.074 Uiso 1 1 calc R . . . .
C0AA C 0.2356(3) 0.5704(3) 1.0454(2) 0.0613(6) Uani 1 1 d . . . . .
H0AA H 0.203301 0.538456 1.111927 0.092 Uiso 1 1 calc GR . . . .
H0AB H 0.358976 0.576400 1.064316 0.092 Uiso 1 1 calc GR . . . .
H0AC H 0.183777 0.490177 0.975665 0.092 Uiso 1 1 calc GR . . . .
C1AA C 0.9088(4) 0.1808(3) 0.5328(3) 0.0776(8) Uani 1 1 d . . . . .
H1AA H 0.994260 0.227604 0.502262 0.116 Uiso 1 1 calc GR . . . .
H1AB H 0.827527 0.105508 0.470075 0.116 Uiso 1 1 calc GR . . . .
H1AC H 0.964030 0.122523 0.597904 0.116 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
N1 C7 1.357(3) . ?
N1 C14 1.376(2) . ?
C2 C4 1.483(2) . ?
C2 C5 1.393(3) . ?
C2 C6 1.390(3) . ?
C3 C8 1.387(3) . ?
C3 C13 1.385(3) . ?
C3 C15 1.485(3) . ?
C4 C12 1.417(3) . ?
C4 C19 1.376(3) . ?
C5 C13 1.378(3) . ?
C6 C8 1.379(3) . ?
C7 C12 1.416(2) . ?
C7 C18 1.390(3) . ?
O9 C15 1.338(3) . ?
O9 C1AA 1.436(2) . ?
O10 C11 1.226(2) . ?
C11 C14 1.452(3) . ?
C11 C0AA 1.501(3) . ?
C12 C16 1.414(3) . ?
C14 C16 1.371(3) . ?
C15 O17 1.199(3) . ?
C18 C20 1.365(3) . ?
C19 C20 1.406(3) . ?

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 N1 C14 109.29(15) . . ?
C5 C2 C4 121.05(17) . . ?
C6 C2 C4 120.44(16) . . ?
C6 C2 C5 118.50(17) . . ?
C8 C3 C15 121.95(18) . . ?
C13 C3 C8 118.90(17) . . ?
C13 C3 C15 119.14(18) . . ?
C12 C4 C2 120.79(17) . . ?
C19 C4 C2 121.73(17) . . ?
C19 C4 C12 117.44(17) . . ?
C13 C5 C2 120.72(19) . . ?
C8 C6 C2 120.60(18) . . ?
N1 C7 C12 107.92(16) . . ?
N1 C7 C18 130.04(17) . . ?
C18 C7 C12 122.03(18) . . ?
C6 C8 C3 120.68(18) . . ?
C15 O9 C1AA 117.25(18) . . ?
O10 C11 C14 120.94(18) . . ?
O10 C11 C0AA 120.69(19) . . ?
C14 C11 C0AA 118.35(17) . . ?
C7 C12 C4 119.45(17) . . ?
C16 C12 C4 134.15(17) . . ?
C16 C12 C7 106.39(16) . . ?
C5 C13 C3 120.58(18) . . ?
N1 C14 C11 120.73(16) . . ?
C16 C14 N1 108.76(17) . . ?
C16 C14 C11 130.46(17) . . ?
O9 C15 C3 111.44(18) . . ?
O17 C15 C3 124.9(2) . . ?
O17 C15 O9 123.64(19) . . ?
C14 C16 C12 107.63(16) . . ?
C20 C18 C7 117.47(18) . . ?
C4 C19 C20 121.8(2) . . ?
C18 C20 C19 121.8(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
