# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_sa5136a_pl
_database_code_depnum_ccdc_archive 'CCDC 1887132'
loop_
_audit_author_name
_audit_author_address
'Guangxi Huang'
;Shenzhen University
China
;
_audit_update_record             
;
2018-12-24 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;
_audit_creation_date             2017-06-15
_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         'C16 H11 N O2'
_chemical_formula_sum            'C16 H11 N O2'
_chemical_formula_weight         249.26
_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                   3.8720(8)
_cell_length_b                   8.1785(15)
_cell_length_c                   19.377(4)
_cell_angle_alpha                77.95(3)
_cell_angle_beta                 87.16(3)
_cell_angle_gamma                88.41(3)
_cell_volume                     599.3(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3008
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4810
_cell_measurement_theta_min      1.8296
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7353
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.083
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8322
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         2.152
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2377
_reflns_number_total             2715
_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       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.226
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2715
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0769
_refine_ls_restrained_S_all      1.226
_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)+(0.0296P)²+0.3777P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1517
_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:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
O1 O -0.4339(5) 0.1999(2) 0.49880(9) 0.0407(5) Uani 1 1 d . . . . .
O2 O -0.2810(5) 0.0584(2) 0.41452(10) 0.0457(5) Uani 1 1 d . . . . .
H2 H -0.374154 -0.017884 0.442974 0.069 Uiso 1 1 calc GR . . . .
N1 N -0.0066(6) 0.6707(3) 0.11674(11) 0.0432(6) Uani 1 1 d . . . . .
C1 C -0.2979(6) 0.1936(3) 0.43963(12) 0.0301(5) Uani 1 1 d . . . . .
C2 C -0.1441(6) 0.3453(3) 0.39385(12) 0.0277(5) Uani 1 1 d . . . . .
C3 C -0.1587(6) 0.4945(3) 0.41766(12) 0.0306(5) Uani 1 1 d . . . . .
H3 H -0.260774 0.497655 0.461841 0.037 Uiso 1 1 calc R . . . .
C4 C -0.0221(6) 0.6383(3) 0.37591(12) 0.0299(5) Uani 1 1 d . . . . .
H4 H -0.027266 0.736755 0.392798 0.036 Uiso 1 1 calc R . . . .
C5 C 0.1242(6) 0.6370(3) 0.30839(11) 0.0268(5) Uani 1 1 d . . . . .
C6 C 0.1448(6) 0.4857(3) 0.28571(12) 0.0290(5) Uani 1 1 d . . . . .
H6 H 0.249059 0.481814 0.241784 0.035 Uiso 1 1 calc R . . . .
C7 C 0.0115(6) 0.3412(3) 0.32792(12) 0.0291(5) Uani 1 1 d . . . . .
H7 H 0.026032 0.241221 0.312144 0.035 Uiso 1 1 calc R . . . .
C8 C 0.2523(6) 0.7963(3) 0.26608(12) 0.0288(5) Uani 1 1 d . . . . .
H8 H 0.339176 0.869495 0.291501 0.035 Uiso 1 1 calc R . . . .
C9 C 0.2607(6) 0.8502(3) 0.19537(11) 0.0256(5) Uani 1 1 d . . . . .
C10 C 0.1156(6) 0.7469(3) 0.15225(12) 0.0300(5) Uani 1 1 d . . . . .
C11 C 0.3886(6) 1.0149(3) 0.15656(11) 0.0249(5) Uani 1 1 d . . . . .
C12 C 0.5451(6) 1.1254(3) 0.19110(12) 0.0293(5) Uani 1 1 d . . . . .
H12 H 0.575424 1.094824 0.239431 0.035 Uiso 1 1 calc R . . . .
C13 C 0.6554(6) 1.2801(3) 0.15393(13) 0.0311(5) Uani 1 1 d . . . . .
H13 H 0.759673 1.352392 0.177474 0.037 Uiso 1 1 calc R . . . .
C14 C 0.6114(6) 1.3277(3) 0.08207(13) 0.0322(6) Uani 1 1 d . . . . .
H14 H 0.684337 1.431930 0.057425 0.039 Uiso 1 1 calc R . . . .
C15 C 0.4586(7) 1.2196(3) 0.04703(13) 0.0335(6) Uani 1 1 d . . . . .
H15 H 0.429240 1.250895 -0.001320 0.040 Uiso 1 1 calc R . . . .
C16 C 0.3492(6) 1.0645(3) 0.08412(12) 0.0290(5) Uani 1 1 d . . . . .
H16 H 0.247484 0.992358 0.060138 0.035 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 C1 1.248(3) . ?
O2 C1 1.296(3) . ?
N1 C10 1.146(3) . ?
C1 C2 1.487(3) . ?
C2 C3 1.391(3) . ?
C2 C7 1.392(3) . ?
C3 C4 1.382(3) . ?
C4 C5 1.401(3) . ?
C5 C6 1.397(3) . ?
C5 C8 1.471(3) . ?
C6 C7 1.386(3) . ?
C8 C9 1.348(3) . ?
C9 C10 1.447(3) . ?
C9 C11 1.484(3) . ?
C11 C12 1.398(3) . ?
C11 C16 1.392(3) . ?
C12 C13 1.386(3) . ?
C13 C14 1.383(3) . ?
C14 C15 1.382(3) . ?
C15 C16 1.387(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
O1 C1 O2 123.2(2) . . ?
O1 C1 C2 120.4(2) . . ?
O2 C1 C2 116.4(2) . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 C7 119.6(2) . . ?
C7 C2 C1 121.5(2) . . ?
C4 C3 C2 120.3(2) . . ?
C3 C4 C5 120.7(2) . . ?
C4 C5 C8 117.5(2) . . ?
C6 C5 C4 118.5(2) . . ?
C6 C5 C8 124.0(2) . . ?
C7 C6 C5 120.7(2) . . ?
C6 C7 C2 120.2(2) . . ?
C9 C8 C5 128.6(2) . . ?
C8 C9 C10 119.1(2) . . ?
C8 C9 C11 125.4(2) . . ?
C10 C9 C11 115.41(19) . . ?
N1 C10 C9 177.2(3) . . ?
C12 C11 C9 121.7(2) . . ?
C16 C11 C9 120.2(2) . . ?
C16 C11 C12 118.1(2) . . ?
C13 C12 C11 120.6(2) . . ?
C14 C13 C12 120.4(2) . . ?
C15 C14 C13 119.7(2) . . ?
C14 C15 C16 119.9(2) . . ?
C15 C16 C11 121.3(2) . . ?

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 C1 C2 C3 -0.9(3) . . . . ?
O1 C1 C2 C7 179.5(2) . . . . ?
O2 C1 C2 C3 179.2(2) . . . . ?
O2 C1 C2 C7 -0.5(3) . . . . ?
C1 C2 C3 C4 -179.1(2) . . . . ?
C1 C2 C7 C6 178.4(2) . . . . ?
C2 C3 C4 C5 1.8(4) . . . . ?
C3 C2 C7 C6 -1.3(3) . . . . ?
C3 C4 C5 C6 -3.2(3) . . . . ?
C3 C4 C5 C8 177.7(2) . . . . ?
C4 C5 C6 C7 2.5(3) . . . . ?
C4 C5 C8 C9 -148.0(2) . . . . ?
C5 C6 C7 C2 -0.2(3) . . . . ?
C5 C8 C9 C10 2.9(4) . . . . ?
C5 C8 C9 C11 178.7(2) . . . . ?
C6 C5 C8 C9 33.0(4) . . . . ?
C7 C2 C3 C4 0.5(3) . . . . ?
C8 C5 C6 C7 -178.6(2) . . . . ?
C8 C9 C11 C12 6.0(4) . . . . ?
C8 C9 C11 C16 -172.8(2) . . . . ?
C9 C11 C12 C13 -178.5(2) . . . . ?
C9 C11 C16 C15 178.3(2) . . . . ?
C10 C9 C11 C12 -178.0(2) . . . . ?
C10 C9 C11 C16 3.2(3) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
C12 C11 C16 C15 -0.6(3) . . . . ?
C12 C13 C14 C15 -0.5(4) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C14 C15 C16 C11 0.3(4) . . . . ?
C16 C11 C12 C13 0.3(3) . . . . ?

_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_m-8-4
_database_code_depnum_ccdc_archive 'CCDC 1887133'
loop_
_audit_author_name
_audit_author_address
'Guangxi Huang'
;Shenzhen University
China
;
_audit_update_record             
;
2018-12-24 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;
_audit_creation_date             2018-07-04
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H13 N O3'
_chemical_formula_sum            'C17 H13 N O3'
_chemical_formula_weight         279.28
_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 0.0180 0.0090 '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 0.0310 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0490 0.0320 '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                   6.8187(2)
_cell_length_b                   7.5408(2)
_cell_length_c                   15.0920(3)
_cell_angle_alpha                82.274(2)
_cell_angle_beta                 84.978(2)
_cell_angle_gamma                64.544(2)
_cell_volume                     693.92(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4128
_cell_measurement_temperature    293.68(10)
_cell_measurement_theta_max      73.6470
_cell_measurement_theta_min      5.8970
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.756
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
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    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6032
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.121
_diffrn_reflns_theta_min         2.957
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.68(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -86.00 -26.00   0.50    0.50    --    0.00 -19.00 120.00  120
  2  ω    -24.00   3.00   0.50    0.50    --    0.00 -77.00 150.00   54
  3  ω    -69.00 -43.00   0.50    0.50    --    0.00 -57.00-120.00   52
  4  ω     21.00  88.00   0.50    0.50    --    0.00  57.00  90.00  134
  5  ω    -21.00   9.00   0.50    0.50    --    0.00 -19.00 120.00   60
  6  ω    -23.00  19.00   0.50    0.50    --    0.00 -57.00-120.00   84
  7  ω     73.00 184.00   0.50    0.50    --   95.20  15.00   0.00  222
  8  ω     73.00 169.00   0.50    0.50    --   95.20  15.00 -60.00  192
  9  ω     27.00 126.00   0.50    0.50    --   95.20 -82.00-180.00  198
 10  ω     29.00 117.00   0.50    0.50    --   95.20 -61.00 -30.00  176
 11  ω     32.00 117.00   0.50    0.50    --   95.20 -61.00-180.00  170
 12  ω     10.00  95.00   0.50    0.50    --   95.20 -15.00   0.00  170
 13  ω     54.00 125.00   0.50    0.50    --   95.20 -82.00  60.00  142
 14  ω     78.00 115.00   0.50    0.50    --   95.20 -77.00-120.00   74
 15  ω     12.00  37.00   0.50    0.50    --   95.20 -82.00  60.00   50
 16  ω     37.00 116.00   0.50    0.50    --   95.20 -82.00 -30.00  158
 17  ω     75.00 112.00   0.50    0.50    --   95.20 -45.00  30.00   74
 18  ω     82.00 108.00   0.50    0.50    --   95.20  82.00 150.00   52
 19  ω     90.00 115.00   0.50    0.50    --   95.20  61.00-120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0492073000
_diffrn_orient_matrix_UB_12      0.0660827000
_diffrn_orient_matrix_UB_13      -0.0971881000
_diffrn_orient_matrix_UB_21      -0.1767931000
_diffrn_orient_matrix_UB_22      -0.0494291000
_diffrn_orient_matrix_UB_23      -0.0325842000
_diffrn_orient_matrix_UB_31      -0.1703046000
_diffrn_orient_matrix_UB_32      0.2120980000
_diffrn_orient_matrix_UB_33      0.0107818000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2417
_reflns_number_total             2723
_reflns_odcompleteness_completeness 99.67
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (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         0.207
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0029(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2723
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.088
_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)+(0.0637P)²+0.0723P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1233
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16),
 C17(H17)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
O1 O 0.57648(19) 0.61600(19) 0.07382(7) 0.0746(3) Uani 1 1 d . . . . .
H1 H 0.5955 0.5759 0.0245 0.112 Uiso 1 1 calc GR . . . .
O2 O 0.31129(18) 0.51592(18) 0.08281(7) 0.0726(3) Uani 1 1 d . . . . .
O3 O 0.0531(2) 0.88134(19) 0.90526(7) 0.0758(3) Uani 1 1 d . . . . .
N1 N 0.72462(18) 0.7488(2) 0.51610(8) 0.0672(4) Uani 1 1 d . . . . .
C1 C 0.4184(2) 0.5896(2) 0.11568(9) 0.0554(3) Uani 1 1 d . . . . .
C2 C 0.3654(2) 0.64564(19) 0.20744(8) 0.0498(3) Uani 1 1 d . . . . .
C3 C 0.5005(2) 0.6985(2) 0.25083(9) 0.0534(3) Uani 1 1 d . . . . .
H3 H 0.6208 0.7074 0.2201 0.064 Uiso 1 1 calc R . . . .
C4 C 0.4589(2) 0.7378(2) 0.33845(9) 0.0524(3) Uani 1 1 d . . . . .
H4 H 0.5523 0.7717 0.3664 0.063 Uiso 1 1 calc R . . . .
C5 C 0.27760(18) 0.72742(17) 0.38650(8) 0.0449(3) Uani 1 1 d . . . . .
C6 C 0.22104(18) 0.75990(18) 0.48053(8) 0.0465(3) Uani 1 1 d . . . . .
H6 H 0.0814 0.7743 0.4983 0.056 Uiso 1 1 calc R . . . .
C7 C 0.33529(18) 0.77265(17) 0.54595(8) 0.0441(3) Uani 1 1 d . . . . .
C8 C 0.55158(19) 0.75904(19) 0.52764(9) 0.0496(3) Uani 1 1 d . . . . .
C9 C 0.25689(18) 0.79910(17) 0.64003(8) 0.0450(3) Uani 1 1 d . . . . .
C10 C 0.0751(2) 0.7688(2) 0.67446(9) 0.0519(3) Uani 1 1 d . . . . .
H10 H 0.0014 0.7310 0.6373 0.062 Uiso 1 1 calc R . . . .
C11 C 0.0023(2) 0.7937(2) 0.76217(9) 0.0548(3) Uani 1 1 d . . . . .
H11 H -0.1187 0.7722 0.7835 0.066 Uiso 1 1 calc R . . . .
C12 C 0.1101(2) 0.8509(2) 0.81836(9) 0.0550(3) Uani 1 1 d . . . . .
C13 C -0.1201(3) 0.8387(3) 0.94527(12) 0.0837(5) Uani 1 1 d . . . . .
H13A H -0.2530 0.9267 0.9167 0.125 Uiso 1 1 calc GR . . . .
H13B H -0.1339 0.8557 1.0078 0.125 Uiso 1 1 calc GR . . . .
H13C H -0.0907 0.7047 0.9384 0.125 Uiso 1 1 calc GR . . . .
C14 C 0.2922(2) 0.8803(2) 0.78509(10) 0.0596(4) Uani 1 1 d . . . . .
H14 H 0.3658 0.9182 0.8223 0.071 Uiso 1 1 calc R . . . .
C15 C 0.3638(2) 0.8537(2) 0.69816(9) 0.0529(3) Uani 1 1 d . . . . .
H15 H 0.4866 0.8726 0.6775 0.063 Uiso 1 1 calc R . . . .
C16 C 0.13896(19) 0.6808(2) 0.34087(9) 0.0513(3) Uani 1 1 d . . . . .
H16 H 0.0147 0.6779 0.3704 0.062 Uiso 1 1 calc R . . . .
C17 C 0.1816(2) 0.6395(2) 0.25368(9) 0.0537(3) Uani 1 1 d . . . . .
H17 H 0.0876 0.6072 0.2252 0.064 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 0.8200 . ?
O1 C1 1.2771(16) . ?
O2 C1 1.2552(17) . ?
O3 C12 1.3560(16) . ?
O3 C13 1.4185(19) . ?
N1 C8 1.1480(15) . ?
C1 C2 1.4715(18) . ?
C2 C3 1.3884(18) . ?
C2 C17 1.3961(17) . ?
C3 H3 0.9300 . ?
C3 C4 1.3726(18) . ?
C4 H4 0.9300 . ?
C4 C5 1.4042(16) . ?
C5 C6 1.4625(17) . ?
C5 C16 1.3984(17) . ?
C6 H6 0.9300 . ?
C6 C7 1.3474(17) . ?
C7 C8 1.4381(15) . ?
C7 C9 1.4809(17) . ?
C9 C10 1.3991(16) . ?
C9 C15 1.3919(17) . ?
C10 H10 0.9300 . ?
C10 C11 1.3806(18) . ?
C11 H11 0.9300 . ?
C11 C12 1.3874(19) . ?
C12 C14 1.3930(18) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14 0.9300 . ?
C14 C15 1.3689(19) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.3707(18) . ?
C17 H17 0.9300 . ?

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
C1 O1 H1 109.5 . . ?
C12 O3 C13 118.58(12) . . ?
O1 C1 C2 117.36(12) . . ?
O2 C1 O1 123.16(13) . . ?
O2 C1 C2 119.46(12) . . ?
C3 C2 C1 120.92(11) . . ?
C3 C2 C17 118.73(12) . . ?
C17 C2 C1 120.30(12) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.90(11) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 120.99(12) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 125.78(11) . . ?
C16 C5 C4 117.37(11) . . ?
C16 C5 C6 116.85(10) . . ?
C5 C6 H6 114.3 . . ?
C7 C6 C5 131.45(11) . . ?
C7 C6 H6 114.3 . . ?
C6 C7 C8 120.53(11) . . ?
C6 C7 C9 125.01(10) . . ?
C8 C7 C9 114.46(10) . . ?
N1 C8 C7 177.62(14) . . ?
C10 C9 C7 121.84(11) . . ?
C15 C9 C7 120.88(11) . . ?
C15 C9 C10 117.28(12) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.72(12) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.82(12) . . ?
C12 C11 H11 120.1 . . ?
O3 C12 C11 125.17(12) . . ?
O3 C12 C14 115.78(12) . . ?
C11 C12 C14 119.05(12) . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14 119.7 . . ?
C15 C14 C12 120.59(12) . . ?
C15 C14 H14 119.7 . . ?
C9 C15 H15 119.2 . . ?
C14 C15 C9 121.54(12) . . ?
C14 C15 H15 119.2 . . ?
C5 C16 H16 119.2 . . ?
C17 C16 C5 121.66(11) . . ?
C17 C16 H16 119.2 . . ?
C2 C17 H17 119.9 . . ?
C16 C17 C2 120.28(12) . . ?
C16 C17 H17 119.9 . . ?

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 C1 C2 C3 -8.8(2) . . . . ?
O1 C1 C2 C17 173.54(13) . . . . ?
O2 C1 C2 C3 169.92(13) . . . . ?
O2 C1 C2 C17 -7.7(2) . . . . ?
O3 C12 C14 C15 -179.94(12) . . . . ?
C1 C2 C3 C4 -175.54(12) . . . . ?
C1 C2 C17 C16 176.29(12) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C3 C2 C17 C16 -1.4(2) . . . . ?
C3 C4 C5 C6 177.96(11) . . . . ?
C3 C4 C5 C16 -1.64(19) . . . . ?
C4 C5 C6 C7 -12.6(2) . . . . ?
C4 C5 C16 C17 2.38(19) . . . . ?
C5 C6 C7 C8 1.8(2) . . . . ?
C5 C6 C7 C9 -177.61(11) . . . . ?
C5 C16 C17 C2 -0.9(2) . . . . ?
C6 C5 C16 C17 -177.25(11) . . . . ?
C6 C7 C9 C10 14.81(19) . . . . ?
C6 C7 C9 C15 -165.81(12) . . . . ?
C7 C9 C10 C11 -179.95(11) . . . . ?
C7 C9 C15 C14 179.47(11) . . . . ?
C8 C7 C9 C10 -164.67(11) . . . . ?
C8 C7 C9 C15 14.71(17) . . . . ?
C9 C10 C11 C12 0.2(2) . . . . ?
C10 C9 C15 C14 -1.1(2) . . . . ?
C10 C11 C12 O3 179.49(13) . . . . ?
C10 C11 C12 C14 -0.6(2) . . . . ?
C11 C12 C14 C15 0.2(2) . . . . ?
C12 C14 C15 C9 0.7(2) . . . . ?
C13 O3 C12 C11 4.9(2) . . . . ?
C13 O3 C12 C14 -175.01(14) . . . . ?
C15 C9 C10 C11 0.6(2) . . . . ?
C16 C5 C6 C7 166.97(13) . . . . ?
C17 C2 C3 C4 2.1(2) . . . . ?

_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 1.440
_oxdiff_exptl_absorpt_empirical_full_min 0.574
####################################################################### 
# 
# 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_m-33-3
_database_code_depnum_ccdc_archive 'CCDC 1949120'
loop_
_audit_author_name
_audit_author_address
'Guangxi Huang'
;Shenzhen University
China
;
_audit_update_record             
;
2019-08-24 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;
_audit_creation_date             2018-08-04
_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         '0.5(C30 H22 N2)'
_chemical_formula_sum            'C15 H11 N'
_chemical_formula_weight         205.25
_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 0.0180 0.0090 '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 0.0310 0.0180 '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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   23.0700(8)
_cell_length_b                   6.8458(2)
_cell_length_c                   7.2886(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1151.11(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1418
_cell_measurement_temperature    268.39(13)
_cell_measurement_theta_max      71.1290
_cell_measurement_theta_min      3.8270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.531
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
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    1.184
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3108
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.718
_diffrn_reflns_theta_min         3.832
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      268.39(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     19.00  87.00   0.50    0.50    --    0.00  82.00 120.00  136
  2  ω    -61.00 -11.00   0.50    0.50    --    0.00 -38.00  90.00  100
  3  ω     28.00  90.00   0.50    1.74    --   95.20 -45.00 150.00  124
  4  ω     14.00  59.00   0.50    1.74    --   95.20 -82.00  90.00   90
  5  ω    119.00 169.00   0.50    1.74    --   95.20  30.00-120.00  100
  6  ω     55.00 120.00   0.50    1.74    --   95.20 -82.00   0.00  130
  7  ω      9.00  80.00   0.50    1.74    --   95.20 -15.00  90.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0020069000
_diffrn_orient_matrix_UB_12      -0.2249168000
_diffrn_orient_matrix_UB_13      0.0034909000
_diffrn_orient_matrix_UB_21      -0.0661195000
_diffrn_orient_matrix_UB_22      -0.0072433000
_diffrn_orient_matrix_UB_23      -0.0291379000
_diffrn_orient_matrix_UB_31      0.0092226000
_diffrn_orient_matrix_UB_32      -0.0028621000
_diffrn_orient_matrix_UB_33      -0.2092680000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                973
_reflns_number_total             1135
_reflns_odcompleteness_completeness 99.84
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (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         0.095
_refine_diff_density_min         -0.094
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.0093(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1135
_refine_ls_number_restraints     108
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0454P)²+0.2269P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1349
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid body (RIGU) restrains
 C1, C2, C3, C6, C7, C8, C9, C4, C5, C10, C11, C12, C13, C14, C15
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Fixed Sof: C1(0.5) C2(0.5) C3(0.5) H3(0.5) C6(0.5) H6(0.5) C7(0.5) H7(0.5)
 C8(0.5) H8(0.5) C9(0.5) H9(0.5) C4(0.5) C5(0.5) H5(0.5) C10(0.5) C11(0.5)
 H11(0.5) C12(0.5) H12(0.5) C13(0.5) H13(0.5) C14(0.5) H14(0.5) C15(0.5)
 H15(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C5(H5), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15)
4.b Fitted hexagon refined as free rotating group:
 C6(C7,C8,C9,C4,C5)
;
_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
N1 N 0.500000 0.2959(3) 0.750000 0.0933(9) Uani 1 2 d S T P . .
C1 C 0.5063(9) 0.4568(3) 0.737(3) 0.049(2) Uani 0.5 1 d . U . A -1
C2 C 0.51981(11) 0.6614(4) 0.7651(4) 0.0476(7) Uani 0.5 1 d . U . A -1
C3 C 0.47990(12) 0.8004(4) 0.7355(4) 0.0526(7) Uani 0.5 1 d . U . A -1
H3 H 0.493119 0.928490 0.742287 0.063 Uiso 0.5 1 calc R . . A -1
C6 C 0.3342(3) 0.9067(12) 0.5367(15) 0.075(2) Uani 0.5 1 d . U . A -1
H6 H 0.317735 1.000516 0.460501 0.090 Uiso 0.5 1 calc R . . A -1
C7 C 0.3002(2) 0.7571(13) 0.6076(17) 0.072(3) Uani 0.5 1 d G U . A -1
H7 H 0.260998 0.750699 0.578871 0.086 Uiso 0.5 1 calc R . . A -1
C8 C 0.3249(3) 0.6169(11) 0.7214(14) 0.069(2) Uani 0.5 1 d G U . A -1
H8 H 0.302133 0.516774 0.768847 0.082 Uiso 0.5 1 calc R . . A -1
C9 C 0.3835(3) 0.6264(8) 0.7643(10) 0.0587(16) Uani 0.5 1 d G U . A -1
H9 H 0.400005 0.532663 0.840455 0.070 Uiso 0.5 1 calc R . . A -1
C4 C 0.4175(2) 0.7761(6) 0.6934(9) 0.0495(12) Uani 0.5 1 d G U . A -1
C5 C 0.3929(3) 0.9163(7) 0.5796(12) 0.0655(17) Uani 0.5 1 d G U . A -1
H5 H 0.415609 1.016405 0.532110 0.079 Uiso 0.5 1 calc R . . A -1
C10 C 0.5806(3) 0.6995(7) 0.8097(9) 0.0518(12) Uani 0.5 1 d . U . A -1
C11 C 0.5969(3) 0.8625(10) 0.9050(14) 0.0692(16) Uani 0.5 1 d . U . A -1
H11 H 0.568735 0.954030 0.935324 0.083 Uiso 0.5 1 calc R . . A -1
C12 C 0.6525(5) 0.8969(17) 0.9574(17) 0.088(2) Uani 0.5 1 d . U . A -1
H12 H 0.661280 1.006616 1.027388 0.105 Uiso 0.5 1 calc R . . A -1
C13 C 0.6948(4) 0.773(2) 0.908(2) 0.094(4) Uani 0.5 1 d . U . A -1
H13 H 0.732977 0.795967 0.942496 0.113 Uiso 0.5 1 calc R . . A -1
C14 C 0.6808(5) 0.6136(17) 0.8084(18) 0.084(3) Uani 0.5 1 d . U . A -1
H14 H 0.709970 0.528526 0.771546 0.101 Uiso 0.5 1 calc R . . A -1
C15 C 0.6246(4) 0.5744(11) 0.7601(12) 0.0683(19) Uani 0.5 1 d . U . A -1
H15 H 0.616164 0.462330 0.693247 0.082 Uiso 0.5 1 calc R . . A -1


_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 C1 1.115(4) . ?
C1 C2 1.450(8) . ?
C2 C3 1.341(3) . ?
C2 C10 1.462(6) . ?
C3 C4 1.481(5) . ?
C6 C7 1.3900 . ?
C6 C5 1.3900 . ?
C7 C8 1.3900 . ?
C8 C9 1.3900 . ?
C9 C4 1.3900 . ?
C4 C5 1.3900 . ?
C10 C11 1.368(7) . ?
C10 C15 1.378(7) . ?
C11 C12 1.358(8) . ?
C12 C13 1.342(9) . ?
C13 C14 1.350(9) . ?
C14 C15 1.369(8) . ?

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
N1 C1 C2 166(3) . . ?
C1 C2 C10 114.2(9) . . ?
C3 C2 C1 121.0(10) . . ?
C3 C2 C10 124.6(3) . . ?
C2 C3 C4 128.4(3) . . ?
C7 C6 C5 120.0 . . ?
C6 C7 C8 120.0 . . ?
C9 C8 C7 120.0 . . ?
C8 C9 C4 120.0 . . ?
C9 C4 C3 123.6(4) . . ?
C5 C4 C3 116.3(4) . . ?
C5 C4 C9 120.0 . . ?
C4 C5 C6 120.0 . . ?
C11 C10 C2 121.6(5) . . ?
C11 C10 C15 115.9(4) . . ?
C15 C10 C2 122.6(6) . . ?
C12 C11 C10 123.0(5) . . ?
C13 C12 C11 120.0(6) . . ?
C12 C13 C14 118.8(6) . . ?
C13 C14 C15 121.5(6) . . ?
C14 C15 C10 120.6(5) . . ?

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
N1 C1 C2 C3 -127(6) . . . . ?
N1 C1 C2 C10 58(6) . . . . ?
C1 C2 C3 C4 7.4(11) . . . . ?
C1 C2 C10 C11 -155.1(11) . . . . ?
C1 C2 C10 C15 24.5(11) . . . . ?
C2 C3 C4 C9 34.3(7) . . . . ?
C2 C3 C4 C5 -147.2(4) . . . . ?
C2 C10 C11 C12 176.3(7) . . . . ?
C2 C10 C15 C14 -178.5(7) . . . . ?
C3 C2 C10 C11 30.6(7) . . . . ?
C3 C2 C10 C15 -149.8(5) . . . . ?
C3 C4 C5 C6 -178.5(5) . . . . ?
C6 C7 C8 C9 0.0 . . . . ?
C7 C6 C5 C4 0.0 . . . . ?
C7 C8 C9 C4 0.0 . . . . ?
C8 C9 C4 C3 178.4(6) . . . . ?
C8 C9 C4 C5 0.0 . . . . ?
C9 C4 C5 C6 0.0 . . . . ?
C5 C6 C7 C8 0.0 . . . . ?
C10 C2 C3 C4 -178.7(7) . . . . ?
C10 C11 C12 C13 3.2(9) . . . . ?
C11 C10 C15 C14 1.1(7) . . . . ?
C11 C12 C13 C14 -0.7(9) . . . . ?
C12 C13 C14 C15 -1.5(9) . . . . ?
C13 C14 C15 C10 1.2(9) . . . . ?
C15 C10 C11 C12 -3.4(8) . . . . ?

_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 1.600
_oxdiff_exptl_absorpt_empirical_full_min 0.446
####################################################################### 
# 
# 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_tx105a
_database_code_depnum_ccdc_archive 'CCDC 1949114'
loop_
_audit_author_name
_audit_author_address
'Guangxi Huang'
;Shenzhen University
China
;
_audit_update_record             
;
2019-08-24 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;
_audit_creation_date             2018-11-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 N O'
_chemical_formula_sum            'C16 H13 N O'
_chemical_formula_weight         235.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
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      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                   7.24230(10)
_cell_length_b                   11.79970(10)
_cell_length_c                   14.43200(10)
_cell_angle_alpha                89.6560(10)
_cell_angle_beta                 82.1710(10)
_cell_angle_gamma                89.4850(10)
_cell_volume                     1221.76(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11556
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      74.8620
_cell_measurement_theta_min      3.0550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.161
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.147
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14790
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.645
_diffrn_reflns_theta_min         3.091
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00 113.00   0.50    0.50    --   47.45  38.00 -60.00  156
  2  ω     97.00 142.00   0.50    1.50    --  103.25  30.00 -90.00   90
  3  ω     69.00 110.00   0.50    1.50    --  103.25 -45.00  60.00   82
  4  ω     68.00 116.00   0.50    1.50    --  103.25-124.00  87.00   96
  5  ω     92.00 117.00   0.50    1.50    --  103.25-125.00  30.00   50
  6  ω     53.00  97.00   0.50    1.50    --  103.25 -94.00 -90.00   88
  7  ω     66.00 107.00   0.50    1.50    --  103.25-125.00-150.00   82
  8  ω     45.00  82.00   0.50    0.50    --   47.45-148.00 -76.00   74
  9  ω     32.00 132.00   0.50    1.50    --  103.25-148.00 -76.00  200
 10  ω     42.00  78.00   0.50    1.50    --  103.25-125.00  30.00   72
 11  ω     31.00  56.00   0.50    0.50    --   47.45-124.00  87.00   50
 12  ω     32.00 104.00   0.50    1.50    --  103.25 -94.00  90.00  144
 13  ω     30.00  96.00   0.50    1.50    --  103.25 -30.00  30.00  132
 14  ω     39.00 118.00   0.50    0.50    --   47.45  38.00  90.00  158
 15  ω    141.00 169.00   0.50    1.50    --  103.25  61.00 150.00   56
 16  ω     95.00 132.00   0.50    1.50    --  103.25 124.00 167.00   74
 17  ω     93.00 137.00   0.50    1.50    --  103.25  61.00 150.00   88
 18  ω     76.00 103.00   0.50    0.50    --   47.45 148.00 -28.00   54
 19  ω     27.00 120.00   0.50    0.50    --   47.45  77.00 -30.00  186
 20  ω    -74.00 -48.00   0.50    0.50    --  -47.45 148.00 -28.00   52
 21  ω   -115.00 -49.00   0.50    1.50    --  -99.00 148.00 -28.00  132
 22  ω   -115.00 -26.00   0.50    1.50    --  -99.00  61.00  30.00  178
 23  ω    -93.00 -39.00   0.50    0.50    --  -47.45 124.00 167.00  108
 24  ω    -81.00 -55.00   0.50    1.50    --  -99.00 124.00 167.00   52
 25  ω   -111.00 -30.00   0.50    1.50    --  -99.00  45.00   0.00  162
 26  ω   -113.00 -79.00   0.50    1.50    --  -99.00  15.00-180.00   68
 27  ω    -74.00 -25.00   0.50    1.50    --  -99.00  15.00-180.00   98
 28  ω    -91.00 -56.00   0.50    0.50    --  -47.45-148.00 -76.00   70
 29  ω   -119.00 -72.00   0.50    0.50    --  -47.45-124.00  87.00   94
 30  ω   -136.00-111.00   0.50    1.50    --  -99.00-148.00 -76.00   50
 31  ω   -144.00 -73.00   0.50    1.50    --  -99.00-124.00  87.00  142
 32  ω   -146.00 -98.00   0.50    1.50    --  -99.00 -45.00 -90.00   96
 33  ω   -160.00 -87.00   0.50    1.50    --  -99.00 -30.00 150.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0419708000
_diffrn_orient_matrix_UB_12      0.0982705000
_diffrn_orient_matrix_UB_13      -0.0649320000
_diffrn_orient_matrix_UB_21      -0.0468954000
_diffrn_orient_matrix_UB_22      0.0777306000
_diffrn_orient_matrix_UB_23      0.0855083000
_diffrn_orient_matrix_UB_31      0.2052971000
_diffrn_orient_matrix_UB_32      0.0367196000
_diffrn_orient_matrix_UB_33      -0.0090881000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4461
_reflns_number_total             4846
_reflns_odcompleteness_completeness 99.93
_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 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4846
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.085
_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)+(0.0529P)²+0.3541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1053
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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), C5(H5), C6(H6), C10(H10), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C21(H21), C22(H22), C26(H26), C28(H28),
  C29(H29), C30(H30), C31(H31), C32(H32)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.65069(13) 0.75085(7) 0.03434(6) 0.0326(2) Uani 1 1 d . . . . .
N1 N 0.78734(19) 0.61600(10) 0.49328(8) 0.0418(3) Uani 1 1 d . . . . .
C1 C 0.67691(16) 0.77313(10) 0.12447(8) 0.0248(2) Uani 1 1 d . . . . .
C2 C 0.62989(16) 0.68594(9) 0.18830(8) 0.0260(2) Uani 1 1 d . . . . .
H2 H 0.578874 0.619492 0.168980 0.031 Uiso 1 1 calc R . . . .
C3 C 0.65877(16) 0.69780(9) 0.28021(8) 0.0252(2) Uani 1 1 d . . . . .
H3 H 0.628936 0.638366 0.322031 0.030 Uiso 1 1 calc R . . . .
C4 C 0.73219(15) 0.79766(9) 0.31181(8) 0.0234(2) Uani 1 1 d . . . . .
C5 C 0.77667(16) 0.88463(9) 0.24683(8) 0.0249(2) Uani 1 1 d . . . . .
H5 H 0.825428 0.951752 0.266218 0.030 Uiso 1 1 calc R . . . .
C6 C 0.74980(16) 0.87326(9) 0.15390(8) 0.0263(2) Uani 1 1 d . . . . .
H6 H 0.780328 0.932185 0.111659 0.032 Uiso 1 1 calc R . . . .
C7 C 0.7025(2) 0.83640(11) -0.03418(9) 0.0355(3) Uani 1 1 d . . . . .
H7A H 0.682628 0.809421 -0.094625 0.053 Uiso 1 1 calc GR . . . .
H7B H 0.831829 0.854208 -0.034959 0.053 Uiso 1 1 calc GR . . . .
H7C H 0.628106 0.903192 -0.019100 0.053 Uiso 1 1 calc GR . . . .
C8 C 0.76029(15) 0.80961(9) 0.41145(8) 0.0237(2) Uani 1 1 d . . . . .
C9 C 0.77474(17) 0.70364(10) 0.45988(8) 0.0278(2) Uani 1 1 d . . . . .
C10 C 0.76639(16) 0.90945(10) 0.45623(8) 0.0263(2) Uani 1 1 d . . . . .
H10 H 0.756830 0.973589 0.419370 0.032 Uiso 1 1 calc R . . . .
C11 C 0.78581(15) 0.93179(10) 0.55418(8) 0.0247(2) Uani 1 1 d . . . . .
C12 C 0.86716(17) 0.85678(10) 0.61270(8) 0.0289(3) Uani 1 1 d . . . . .
H12 H 0.918997 0.788858 0.588792 0.035 Uiso 1 1 calc R . . . .
C13 C 0.87114(17) 0.88281(11) 0.70596(8) 0.0304(3) Uani 1 1 d . . . . .
H13 H 0.924645 0.831954 0.744200 0.036 Uiso 1 1 calc R . . . .
C14 C 0.79592(17) 0.98416(11) 0.74268(8) 0.0305(3) Uani 1 1 d . . . . .
H14 H 0.796707 1.000560 0.805571 0.037 Uiso 1 1 calc R . . . .
C15 C 0.71950(17) 1.06094(10) 0.68506(9) 0.0309(3) Uani 1 1 d . . . . .
H15 H 0.670677 1.129530 0.709052 0.037 Uiso 1 1 calc R . . . .
C16 C 0.71601(17) 1.03528(10) 0.59168(8) 0.0285(3) Uani 1 1 d . . . . .
H16 H 0.666446 1.087707 0.553277 0.034 Uiso 1 1 calc R . . . .
O2 O 0.34810(12) 0.74740(7) 0.55780(5) 0.0299(2) Uani 1 1 d . . . . .
N2 N 0.21076(19) 0.88506(10) 1.03560(8) 0.0436(3) Uani 1 1 d . . . . .
C17 C 0.31437(15) 0.72713(9) 0.65175(8) 0.0236(2) Uani 1 1 d . . . . .
C18 C 0.22844(16) 0.63073(10) 0.69249(8) 0.0259(2) Uani 1 1 d . . . . .
H18 H 0.192360 0.573247 0.655131 0.031 Uiso 1 1 calc R . . . .
C19 C 0.19673(16) 0.62068(9) 0.78925(8) 0.0255(2) Uani 1 1 d . . . . .
H19 H 0.138736 0.556102 0.816080 0.031 Uiso 1 1 calc R . . . .
C20 C 0.24983(15) 0.70516(9) 0.84707(8) 0.0234(2) Uani 1 1 d . . . . .
C21 C 0.33438(15) 0.80214(9) 0.80425(8) 0.0245(2) Uani 1 1 d . . . . .
H21 H 0.368488 0.860429 0.841383 0.029 Uiso 1 1 calc R . . . .
C22 C 0.36794(16) 0.81283(9) 0.70841(8) 0.0251(2) Uani 1 1 d . . . . .
H22 H 0.426333 0.877215 0.681435 0.030 Uiso 1 1 calc R . . . .
C23 C 0.30120(18) 0.66032(11) 0.49717(8) 0.0323(3) Uani 1 1 d . . . . .
H23A H 0.327556 0.685500 0.433401 0.048 Uiso 1 1 calc GR . . . .
H23B H 0.170987 0.643417 0.511487 0.048 Uiso 1 1 calc GR . . . .
H23C H 0.373488 0.593445 0.505825 0.048 Uiso 1 1 calc GR . . . .
C24 C 0.22626(15) 0.69227(9) 0.95039(8) 0.0243(2) Uani 1 1 d . . . . .
C25 C 0.21722(17) 0.79756(10) 1.00096(8) 0.0285(3) Uani 1 1 d . . . . .
C26 C 0.22576(16) 0.59157(10) 0.99542(8) 0.0259(2) Uani 1 1 d . . . . .
H26 H 0.233172 0.528268 0.956967 0.031 Uiso 1 1 calc R . . . .
C27 C 0.21533(15) 0.56685(9) 1.09556(8) 0.0236(2) Uani 1 1 d . . . . .
C28 C 0.29177(16) 0.46350(10) 1.12107(8) 0.0276(2) Uani 1 1 d . . . . .
H28 H 0.340611 0.412976 1.074703 0.033 Uiso 1 1 calc R . . . .
C29 C 0.29582(17) 0.43533(10) 1.21410(9) 0.0304(3) Uani 1 1 d . . . . .
H29 H 0.348897 0.366959 1.229670 0.036 Uiso 1 1 calc R . . . .
C30 C 0.22075(17) 0.50906(11) 1.28400(8) 0.0302(3) Uani 1 1 d . . . . .
H30 H 0.223558 0.490588 1.346529 0.036 Uiso 1 1 calc R . . . .
C31 C 0.14128(16) 0.61078(10) 1.25980(8) 0.0293(3) Uani 1 1 d . . . . .
H31 H 0.089849 0.660022 1.306605 0.035 Uiso 1 1 calc R . . . .
C32 C 0.13763(16) 0.63984(10) 1.16688(8) 0.0264(2) Uani 1 1 d . . . . .
H32 H 0.083387 0.708057 1.151827 0.032 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 C1 1.3673(13) . ?
O1 C7 1.4253(15) . ?
N1 C9 1.1465(16) . ?
C1 C2 1.3902(16) . ?
C1 C6 1.3904(16) . ?
C2 C3 1.3787(16) . ?
C3 C4 1.4011(15) . ?
C4 C5 1.3959(16) . ?
C4 C8 1.4871(15) . ?
C5 C6 1.3886(16) . ?
C8 C9 1.4388(16) . ?
C8 C10 1.3510(16) . ?
C10 C11 1.4651(15) . ?
C11 C12 1.4005(16) . ?
C11 C16 1.4007(16) . ?
C12 C13 1.3865(16) . ?
C13 C14 1.3874(17) . ?
C14 C15 1.3877(18) . ?
C15 C16 1.3866(17) . ?
O2 C17 1.3646(13) . ?
O2 C23 1.4264(14) . ?
N2 C25 1.1477(16) . ?
C17 C18 1.3900(16) . ?
C17 C22 1.3946(16) . ?
C18 C19 1.3884(16) . ?
C19 C20 1.3936(15) . ?
C20 C21 1.4026(16) . ?
C20 C24 1.4846(15) . ?
C21 C22 1.3766(16) . ?
C24 C25 1.4411(15) . ?
C24 C26 1.3507(16) . ?
C26 C27 1.4645(15) . ?
C27 C28 1.4026(16) . ?
C27 C32 1.4008(16) . ?
C28 C29 1.3853(17) . ?
C29 C30 1.3866(17) . ?
C30 C31 1.3897(18) . ?
C31 C32 1.3859(16) . ?

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
C1 O1 C7 117.49(9) . . ?
O1 C1 C2 115.47(10) . . ?
O1 C1 C6 124.65(10) . . ?
C2 C1 C6 119.85(10) . . ?
C3 C2 C1 120.11(10) . . ?
C2 C3 C4 121.27(10) . . ?
C3 C4 C8 120.59(10) . . ?
C5 C4 C3 117.70(10) . . ?
C5 C4 C8 121.70(10) . . ?
C6 C5 C4 121.53(10) . . ?
C5 C6 C1 119.51(10) . . ?
C9 C8 C4 114.22(9) . . ?
C10 C8 C4 124.71(10) . . ?
C10 C8 C9 121.04(10) . . ?
N1 C9 C8 175.82(12) . . ?
C8 C10 C11 129.68(11) . . ?
C12 C11 C10 124.67(10) . . ?
C12 C11 C16 118.05(10) . . ?
C16 C11 C10 117.28(10) . . ?
C13 C12 C11 120.62(11) . . ?
C12 C13 C14 120.51(11) . . ?
C13 C14 C15 119.65(11) . . ?
C16 C15 C14 119.94(11) . . ?
C15 C16 C11 121.17(11) . . ?
C17 O2 C23 117.39(9) . . ?
O2 C17 C18 124.72(10) . . ?
O2 C17 C22 115.54(10) . . ?
C18 C17 C22 119.72(10) . . ?
C19 C18 C17 119.66(10) . . ?
C18 C19 C20 121.50(10) . . ?
C19 C20 C21 117.72(10) . . ?
C19 C20 C24 121.85(10) . . ?
C21 C20 C24 120.38(10) . . ?
C22 C21 C20 121.38(10) . . ?
C21 C22 C17 120.01(10) . . ?
C25 C24 C20 114.55(10) . . ?
C26 C24 C20 124.13(10) . . ?
C26 C24 C25 121.17(10) . . ?
N2 C25 C24 175.43(13) . . ?
C24 C26 C27 129.87(10) . . ?
C28 C27 C26 117.21(10) . . ?
C32 C27 C26 124.57(10) . . ?
C32 C27 C28 118.20(10) . . ?
C29 C28 C27 121.19(11) . . ?
C28 C29 C30 120.01(11) . . ?
C29 C30 C31 119.43(11) . . ?
C32 C31 C30 120.90(11) . . ?
C31 C32 C27 120.24(11) . . ?

_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 3.727
_oxdiff_exptl_absorpt_empirical_full_min 0.250
