# Electronic Supplementary Material (ESI) for Analyst.
# This journal is © The Royal Society of Chemistry 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_a
_database_code_depnum_ccdc_archive 'CCDC 2009448'
loop_
_audit_author_name
_audit_author_address
'Sijing Zhang'
;Anhui University
China
;
_audit_update_record             
;
2020-06-12 deposited with the CCDC.	2020-09-23 downloaded from the CCDC.
;
_audit_creation_date             2018-10-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H12 F N O'
_chemical_formula_sum            'C17 H12 F N O'
_chemical_formula_weight         265.28
_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 0.0033 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'
F F 0.0171 0.0103 '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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.7867(11)
_cell_length_b                   14.848(2)
_cell_length_c                   13.118(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.182(2)
_cell_angle_gamma                90
_cell_volume                     1296.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2144
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.008
_cell_measurement_theta_min      2.744
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6779
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0755 before and 0.0429 after correction.
The Ratio of minimum to maximum transmission is 0.9092.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             552
_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  0.0234
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10018
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.362
_diffrn_reflns_theta_min         2.094
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1743
_reflns_number_total             2712
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.109
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2712
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.017
_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)+(0.0467P)²+0.1057P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.1067
_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:
 C8(H8), C11(H11), C7(H7), C13(H13), C3(H3), C5(H5), C17(H17), C14(H14),
 C4(H4), C16(H16), C10(H10)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.22024(17) 0.41559(7) 1.11157(8) 0.0950(4) Uani 1 1 d . . . . .
O1 O 0.63960(16) 0.45523(9) 0.36476(8) 0.0742(4) Uani 1 1 d . . . . .
H1 H 0.5864 0.4549 0.4158 0.111 Uiso 1 1 calc GR . . . .
N1 N 0.76358(17) 0.39283(7) 0.55985(9) 0.0475(3) Uani 1 1 d . . . . .
C8 C 1.0101(2) 0.31773(9) 0.68670(11) 0.0540(4) Uani 1 1 d . . . . .
H8 H 1.0456 0.2937 0.7532 0.065 Uiso 1 1 calc R . . . .
C11 C 0.7114(2) 0.34714(9) 0.82573(11) 0.0533(4) Uani 1 1 d . . . . .
H11 H 0.8262 0.3133 0.8502 0.064 Uiso 1 1 calc R . . . .
C7 C 1.1386(2) 0.31124(10) 0.62016(11) 0.0564(4) Uani 1 1 d . . . . .
H7 H 1.2628 0.2837 0.6415 0.068 Uiso 1 1 calc R . . . .
C13 C 0.3949(2) 0.40679(10) 0.87025(12) 0.0576(4) Uani 1 1 d . . . . .
H13 H 0.3519 0.4243 0.8015 0.069 Uiso 1 1 calc R . . . .
C3 C 0.9506(2) 0.41666(10) 0.32030(11) 0.0582(4) Uani 1 1 d . . . . .
H3 H 0.9068 0.4395 0.2537 0.070 Uiso 1 1 calc R . . . .
C5 C 1.2100(2) 0.34428(10) 0.44415(12) 0.0586(4) Uani 1 1 d . . . . .
H5 H 1.3377 0.3191 0.4608 0.070 Uiso 1 1 calc R . . . .
C17 C 0.6397(2) 0.33984(10) 1.00329(11) 0.0592(4) Uani 1 1 d . . . . .
H17 H 0.7627 0.3112 1.0245 0.071 Uiso 1 1 calc R . . . .
C14 C 0.2737(2) 0.42342(10) 0.94098(12) 0.0633(4) Uani 1 1 d . . . . .
H14 H 0.1495 0.4512 0.9206 0.076 Uiso 1 1 calc R . . . .
C4 C 1.1430(2) 0.37955(11) 0.34799(12) 0.0610(4) Uani 1 1 d . . . . .
H4 H 1.2268 0.3790 0.2997 0.073 Uiso 1 1 calc R . . . .
C15 C 0.3406(3) 0.39808(10) 1.04193(13) 0.0640(4) Uani 1 1 d . . . . .
C16 C 0.5211(3) 0.35683(11) 1.07511(12) 0.0672(5) Uani 1 1 d . . . . .
H16 H 0.5629 0.3406 1.1444 0.081 Uiso 1 1 calc R . . . .
C1 C 0.8928(2) 0.38521(8) 0.49253(10) 0.0439(3) Uani 1 1 d . . . . .
C6 C 1.0851(2) 0.34611(9) 0.51854(11) 0.0489(3) Uani 1 1 d . . . . .
C9 C 0.8217(2) 0.36084(9) 0.65579(10) 0.0462(3) Uani 1 1 d . . . . .
C12 C 0.5794(2) 0.36458(9) 0.89912(10) 0.0505(4) Uani 1 1 d . . . . .
C2 C 0.8276(2) 0.41940(9) 0.39067(11) 0.0516(4) Uani 1 1 d . . . . .
C10 C 0.6848(2) 0.37456(9) 0.72748(11) 0.0520(4) Uani 1 1 d . . . . .
H10 H 0.5667 0.4057 0.7018 0.062 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
F1 C15 1.3634(17) . ?
O1 C2 1.3629(16) . ?
N1 C1 1.3646(16) . ?
N1 C9 1.3313(16) . ?
C8 C7 1.3516(18) . ?
C8 C9 1.4169(19) . ?
C11 C12 1.4598(19) . ?
C11 C10 1.3301(19) . ?
C7 C6 1.4104(19) . ?
C13 C14 1.376(2) . ?
C13 C12 1.386(2) . ?
C3 C4 1.399(2) . ?
C3 C2 1.3602(19) . ?
C5 C4 1.360(2) . ?
C5 C6 1.4117(19) . ?
C17 C16 1.376(2) . ?
C17 C12 1.3973(19) . ?
C14 C15 1.367(2) . ?
C15 C16 1.363(2) . ?
C1 C6 1.4085(19) . ?
C1 C2 1.4176(19) . ?
C9 C10 1.4587(18) . ?

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
C9 N1 C1 118.19(12) . . ?
C7 C8 C9 120.45(13) . . ?
C10 C11 C12 126.82(14) . . ?
C8 C7 C6 120.28(13) . . ?
C14 C13 C12 121.56(14) . . ?
C2 C3 C4 120.04(14) . . ?
C4 C5 C6 119.74(14) . . ?
C16 C17 C12 121.48(15) . . ?
C15 C14 C13 118.31(16) . . ?
C5 C4 C3 121.33(14) . . ?
F1 C15 C14 117.85(17) . . ?
C16 C15 F1 119.33(15) . . ?
C16 C15 C14 122.82(15) . . ?
C15 C16 C17 118.20(14) . . ?
N1 C1 C6 123.98(12) . . ?
N1 C1 C2 117.24(12) . . ?
C6 C1 C2 118.78(12) . . ?
C7 C6 C5 124.57(14) . . ?
C1 C6 C7 115.90(13) . . ?
C1 C6 C5 119.53(13) . . ?
N1 C9 C8 121.14(13) . . ?
N1 C9 C10 116.79(12) . . ?
C8 C9 C10 122.05(12) . . ?
C13 C12 C11 122.52(13) . . ?
C13 C12 C17 117.63(14) . . ?
C17 C12 C11 119.84(14) . . ?
O1 C2 C1 118.75(12) . . ?
C3 C2 O1 120.70(13) . . ?
C3 C2 C1 120.55(14) . . ?
C11 C10 C9 126.74(14) . . ?

_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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2009458'
loop_
_audit_author_name
_audit_author_address
'Sijing Zhang'
;Anhui University
China
;
_audit_update_record             
;
2020-06-12 deposited with the CCDC.	2020-09-23 downloaded from the CCDC.
;
_audit_creation_date             2019-07-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H22 N2 O'
_chemical_formula_sum            'C21 H22.50 N2 O'
_chemical_formula_weight         318.91
_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                   11.151(2)
_cell_length_b                   12.493(3)
_cell_length_c                   15.327(3)
_cell_angle_alpha                104.622(2)
_cell_angle_beta                 101.560(2)
_cell_angle_gamma                114.181(2)
_cell_volume                     1769.6(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5657
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.998
_cell_measurement_theta_min      2.525
_shelx_estimated_absorpt_T_max   0.7455
_shelx_estimated_absorpt_T_min   0.5452
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5452
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1012 before and 0.0352 after correction.
The Ratio of minimum to maximum transmission is 0.7313.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block-shaped
_exptl_crystal_F_000             682
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13901
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.447
_diffrn_reflns_theta_min         1.462
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5218
_reflns_number_total             7041
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         7041
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0566
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0990P)²+0.2002P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1580
_refine_ls_wR_factor_ref         0.1757
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B), C24(H24A,H24B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C14(H14), C33(H33), C7(H7), C19(H19), C20(H20), C15(H15),
 C21(H21), C6(H6), C32(H32), C31(H31), C30(H30), C9(H9), C10(H10), C40(H40),
 C36(H36), C35(H35), C27(H27), C28(H28), C41(H41), C42(H42)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C1(H1A,H1B,H1C), C25(H25A,H25B,H25C), C22(H22A,H22B,H22C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.44360(12) 0.20832(10) 0.62721(9) 0.0538(3) Uani 1 1 d . . . . .
H1 H 0.4691 0.2835 0.6387 0.081 Uiso 1 1 calc GR . . . .
O2 O 0.41212(13) 0.40424(11) 0.77803(8) 0.0554(3) Uani 1 1 d . . . . .
H2 H 0.3642 0.3538 0.7228 0.083 Uiso 1 1 calc GR . . . .
N3 N 0.21051(13) 0.24630(11) 0.59830(9) 0.0399(3) Uani 1 1 d . . . . .
N2 N 0.54992(13) 0.46047(11) 0.64825(8) 0.0410(3) Uani 1 1 d . . . . .
N1 N 0.72401(18) 0.00998(14) 0.19137(11) 0.0627(4) Uani 1 1 d . . . . .
C17 C 0.21448(16) 0.15700(12) 0.52744(10) 0.0399(3) Uani 1 1 d . . . . .
N4 N -0.04852(17) 0.68049(16) 0.99538(11) 0.0654(4) Uani 1 1 d . . . . .
C13 C 0.09852(16) 0.26288(13) 0.58340(11) 0.0409(3) Uani 1 1 d . . . . .
C38 C 0.54429(15) 0.55414(14) 0.71372(10) 0.0415(3) Uani 1 1 d . . . . .
C8 C -0.02143(17) 0.44931(14) 0.75432(11) 0.0443(4) Uani 1 1 d . . . . .
C12 C 0.09394(17) 0.34978(14) 0.66521(11) 0.0448(4) Uani 1 1 d . . . . .
H12 H 0.1753 0.3980 0.7188 0.054 Uiso 1 1 calc R . . . .
C16 C 0.10265(17) 0.08098(13) 0.43813(11) 0.0458(4) Uani 1 1 d . . . . .
C18 C 0.33217(17) 0.13739(14) 0.54414(12) 0.0448(4) Uani 1 1 d . . . . .
C39 C 0.47277(16) 0.52389(15) 0.77861(11) 0.0465(4) Uani 1 1 d . . . . .
C11 C -0.01503(17) 0.36695(14) 0.67075(11) 0.0447(4) Uani 1 1 d . . . . .
H11 H -0.0949 0.3221 0.6160 0.054 Uiso 1 1 calc R . . . .
C34 C 0.62147(16) 0.48994(14) 0.58991(11) 0.0433(4) Uani 1 1 d . . . . .
C14 C -0.01200(17) 0.19608(15) 0.49355(11) 0.0488(4) Uani 1 1 d . . . . .
H14 H -0.0858 0.2137 0.4829 0.059 Uiso 1 1 calc R . . . .
C33 C 0.62694(17) 0.38732(15) 0.52310(11) 0.0470(4) Uani 1 1 d . . . . .
H33 H 0.5726 0.3062 0.5207 0.056 Uiso 1 1 calc R . . . .
C29 C 0.70638(18) 0.29661(15) 0.39664(12) 0.0499(4) Uani 1 1 d . . . . .
C7 C 0.09478(17) 0.53276(15) 0.83734(12) 0.0519(4) Uani 1 1 d . . . . .
H7 H 0.1811 0.5383 0.8393 0.062 Uiso 1 1 calc R . . . .
C19 C 0.3311(2) 0.04047(15) 0.47638(14) 0.0552(4) Uani 1 1 d . . . . .
H19 H 0.4065 0.0252 0.4886 0.066 Uiso 1 1 calc R . . . .
C37 C 0.60968(17) 0.68168(15) 0.72062(12) 0.0492(4) Uani 1 1 d . . . . .
C20 C 0.2196(2) -0.03538(15) 0.38975(14) 0.0589(5) Uani 1 1 d . . . . .
H20 H 0.2218 -0.1001 0.3452 0.071 Uiso 1 1 calc R . . . .
C15 C -0.00986(18) 0.10657(15) 0.42330(12) 0.0513(4) Uani 1 1 d . . . . .
H15 H -0.0833 0.0617 0.3648 0.062 Uiso 1 1 calc R . . . .
C5 C -0.04057(18) 0.60451(16) 0.91708(12) 0.0506(4) Uani 1 1 d . . . . .
C21 C 0.1081(2) -0.01555(15) 0.36990(12) 0.0554(4) Uani 1 1 d . . . . .
H21 H 0.0352 -0.0655 0.3114 0.067 Uiso 1 1 calc R . . . .
C6 C 0.08605(18) 0.60670(16) 0.91600(13) 0.0560(4) Uani 1 1 d . . . . .
H6 H 0.1661 0.6598 0.9701 0.067 Uiso 1 1 calc R . . . .
C32 C 0.70160(19) 0.39796(16) 0.46530(12) 0.0525(4) Uani 1 1 d . . . . .
H32 H 0.7573 0.4795 0.4691 0.063 Uiso 1 1 calc R . . . .
C31 C 0.63545(19) 0.07516(16) 0.31638(12) 0.0536(4) Uani 1 1 d . . . . .
H31 H 0.5838 -0.0084 0.3100 0.064 Uiso 1 1 calc R . . . .
C26 C 0.71632(18) 0.10288(16) 0.25750(11) 0.0505(4) Uani 1 1 d . . . . .
C30 C 0.63137(19) 0.16899(16) 0.38292(12) 0.0528(4) Uani 1 1 d . . . . .
H30 H 0.5765 0.1469 0.4205 0.063 Uiso 1 1 calc R . . . .
C9 C -0.14686(18) 0.44641(17) 0.75572(12) 0.0539(4) Uani 1 1 d . . . . .
H9 H -0.2269 0.3919 0.7019 0.065 Uiso 1 1 calc R . . . .
C10 C -0.15729(19) 0.52121(18) 0.83383(12) 0.0582(5) Uani 1 1 d . . . . .
H10 H -0.2435 0.5163 0.8312 0.070 Uiso 1 1 calc R . . . .
C40 C 0.47014(18) 0.61814(17) 0.84624(12) 0.0564(5) Uani 1 1 d . . . . .
H40 H 0.4257 0.5987 0.8897 0.068 Uiso 1 1 calc R . . . .
C36 C 0.6824(2) 0.70851(16) 0.65656(14) 0.0588(5) Uani 1 1 d . . . . .
H36 H 0.7259 0.7907 0.6581 0.071 Uiso 1 1 calc R . . . .
C35 C 0.68914(19) 0.61594(16) 0.59324(13) 0.0547(4) Uani 1 1 d . . . . .
H35 H 0.7381 0.6345 0.5518 0.066 Uiso 1 1 calc R . . . .
C27 C 0.7924(2) 0.23052(18) 0.27137(14) 0.0632(5) Uani 1 1 d . . . . .
H27 H 0.8478 0.2533 0.2342 0.076 Uiso 1 1 calc R . . . .
C28 C 0.7869(2) 0.32276(17) 0.33884(15) 0.0634(5) Uani 1 1 d . . . . .
H28 H 0.8395 0.4066 0.3461 0.076 Uiso 1 1 calc R . . . .
C3 C -0.1731(2) 0.69437(19) 0.99171(14) 0.0645(5) Uani 1 1 d . . . . .
H3A H -0.2193 0.6827 0.9266 0.077 Uiso 1 1 calc R . . . .
H3B H -0.1445 0.7798 1.0331 0.077 Uiso 1 1 calc R . . . .
C41 C 0.5334(2) 0.74342(18) 0.85080(14) 0.0654(5) Uani 1 1 d . . . . .
H41 H 0.5290 0.8055 0.8964 0.078 Uiso 1 1 calc R . . . .
C42 C 0.6012(2) 0.77463(16) 0.78912(14) 0.0640(5) Uani 1 1 d . . . . .
H42 H 0.6420 0.8577 0.7923 0.077 Uiso 1 1 calc R . . . .
C2 C 0.0622(2) 0.74033(19) 1.09039(14) 0.0696(5) Uani 1 1 d . . . . .
H2A H 0.1083 0.6898 1.0944 0.084 Uiso 1 1 calc R . . . .
H2B H 0.0198 0.7421 1.1398 0.084 Uiso 1 1 calc R . . . .
C24 C 0.7892(2) 0.0375(2) 0.12060(14) 0.0715(6) Uani 1 1 d . . . . .
H24A H 0.7736 0.1018 0.1039 0.086 Uiso 1 1 calc R . . . .
H24B H 0.7436 -0.0384 0.0629 0.086 Uiso 1 1 calc R . . . .
C23 C 0.6535(2) -0.12139(17) 0.18254(15) 0.0718(6) Uani 1 1 d . . . . .
H23A H 0.6610 -0.1232 0.2463 0.086 Uiso 1 1 calc R . . . .
H23B H 0.7024 -0.1630 0.1565 0.086 Uiso 1 1 calc R . . . .
C4 C -0.2757(3) 0.6024(3) 1.02214(19) 0.0884(7) Uani 1 1 d . . . . .
H4A H -0.3030 0.5175 0.9824 0.133 Uiso 1 1 calc GR . . . .
H4B H -0.3568 0.6135 1.0154 0.133 Uiso 1 1 calc GR . . . .
H4C H -0.2328 0.6172 1.0880 0.133 Uiso 1 1 calc GR . . . .
C1 C 0.1680(3) 0.8713(2) 1.10857(19) 0.0911(7) Uani 1 1 d . . . . .
H1A H 0.2122 0.8699 1.0609 0.137 Uiso 1 1 calc GR . . . .
H1B H 0.2374 0.9068 1.1711 0.137 Uiso 1 1 calc GR . . . .
H1C H 0.1230 0.9220 1.1054 0.137 Uiso 1 1 calc GR . . . .
C25 C 0.9441(3) 0.0825(3) 0.1541(2) 0.0933(8) Uani 1 1 d . . . . .
H25A H 0.9798 0.0985 0.1041 0.140 Uiso 1 1 calc GR . . . .
H25B H 0.9606 0.0187 0.1694 0.140 Uiso 1 1 calc GR . . . .
H25C H 0.9906 0.1590 0.2102 0.140 Uiso 1 1 calc GR . . . .
C22 C 0.5021(3) -0.1959(3) 0.1207(2) 0.1123(10) Uani 1 1 d . . . . .
H22A H 0.4928 -0.1944 0.0574 0.168 Uiso 1 1 calc GR . . . .
H22B H 0.4511 -0.1591 0.1480 0.168 Uiso 1 1 calc GR . . . .
H22C H 0.4653 -0.2817 0.1170 0.168 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
O1 C18 1.358(2) . ?
O2 C39 1.362(2) . ?
N3 C17 1.3690(18) . ?
N3 C13 1.333(2) . ?
N2 C38 1.3685(19) . ?
N2 C34 1.335(2) . ?
N1 C26 1.380(2) . ?
N1 C24 1.457(2) . ?
N1 C23 1.455(2) . ?
C17 C16 1.421(2) . ?
C17 C18 1.417(2) . ?
N4 C5 1.373(2) . ?
N4 C3 1.461(2) . ?
N4 C2 1.475(3) . ?
C13 C12 1.462(2) . ?
C13 C14 1.417(2) . ?
C38 C39 1.424(2) . ?
C38 C37 1.419(2) . ?
C8 C11 1.461(2) . ?
C8 C7 1.396(2) . ?
C8 C9 1.389(2) . ?
C12 C11 1.332(2) . ?
C16 C15 1.407(2) . ?
C16 C21 1.415(2) . ?
C18 C19 1.376(2) . ?
C39 C40 1.373(2) . ?
C34 C33 1.457(2) . ?
C34 C35 1.422(2) . ?
C14 C15 1.354(2) . ?
C33 C32 1.327(2) . ?
C29 C32 1.455(2) . ?
C29 C30 1.398(2) . ?
C29 C28 1.386(2) . ?
C7 C6 1.369(2) . ?
C19 C20 1.395(3) . ?
C37 C36 1.413(3) . ?
C37 C42 1.405(2) . ?
C20 C21 1.356(3) . ?
C5 C6 1.405(2) . ?
C5 C10 1.400(2) . ?
C31 C26 1.406(2) . ?
C31 C30 1.369(2) . ?
C26 C27 1.399(2) . ?
C9 C10 1.378(2) . ?
C40 C41 1.405(3) . ?
C36 C35 1.349(2) . ?
C27 C28 1.372(2) . ?
C3 C4 1.501(3) . ?
C41 C42 1.359(3) . ?
C2 C1 1.485(3) . ?
C24 C25 1.506(3) . ?
C23 C22 1.497(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
C13 N3 C17 119.20(13) . . ?
C34 N2 C38 119.16(13) . . ?
C26 N1 C24 120.92(15) . . ?
C26 N1 C23 121.24(15) . . ?
C23 N1 C24 117.47(15) . . ?
N3 C17 C16 122.07(14) . . ?
N3 C17 C18 119.18(13) . . ?
C18 C17 C16 118.73(13) . . ?
C5 N4 C3 121.93(15) . . ?
C5 N4 C2 121.17(16) . . ?
C3 N4 C2 116.54(15) . . ?
N3 C13 C12 116.54(13) . . ?
N3 C13 C14 121.30(13) . . ?
C14 C13 C12 122.13(14) . . ?
N2 C38 C39 119.28(14) . . ?
N2 C38 C37 122.24(14) . . ?
C37 C38 C39 118.47(14) . . ?
C7 C8 C11 123.05(15) . . ?
C9 C8 C11 120.95(14) . . ?
C9 C8 C7 115.98(14) . . ?
C11 C12 C13 126.59(15) . . ?
C15 C16 C17 116.83(13) . . ?
C15 C16 C21 123.47(15) . . ?
C21 C16 C17 119.70(16) . . ?
O1 C18 C17 121.69(13) . . ?
O1 C18 C19 119.00(15) . . ?
C19 C18 C17 119.26(15) . . ?
O2 C39 C38 121.39(14) . . ?
O2 C39 C40 119.01(15) . . ?
C40 C39 C38 119.54(15) . . ?
C12 C11 C8 126.42(15) . . ?
N2 C34 C33 116.99(14) . . ?
N2 C34 C35 121.27(14) . . ?
C35 C34 C33 121.75(15) . . ?
C15 C14 C13 119.84(15) . . ?
C32 C33 C34 126.54(16) . . ?
C30 C29 C32 123.79(15) . . ?
C28 C29 C32 120.60(15) . . ?
C28 C29 C30 115.60(15) . . ?
C6 C7 C8 122.26(15) . . ?
C18 C19 C20 121.52(17) . . ?
C36 C37 C38 116.82(15) . . ?
C42 C37 C38 120.17(16) . . ?
C42 C37 C36 123.01(16) . . ?
C21 C20 C19 120.60(15) . . ?
C14 C15 C16 120.51(15) . . ?
N4 C5 C6 121.63(15) . . ?
N4 C5 C10 122.19(15) . . ?
C10 C5 C6 116.18(15) . . ?
C20 C21 C16 120.07(16) . . ?
C7 C6 C5 121.73(15) . . ?
C33 C32 C29 127.46(16) . . ?
C30 C31 C26 121.19(16) . . ?
N1 C26 C31 122.06(15) . . ?
N1 C26 C27 121.45(16) . . ?
C27 C26 C31 116.46(15) . . ?
C31 C30 C29 122.62(15) . . ?
C10 C9 C8 122.55(15) . . ?
C9 C10 C5 121.29(16) . . ?
C39 C40 C41 121.10(17) . . ?
C35 C36 C37 120.53(16) . . ?
C36 C35 C34 119.97(16) . . ?
C28 C27 C26 121.17(16) . . ?
C27 C28 C29 122.96(16) . . ?
N4 C3 C4 113.39(18) . . ?
C42 C41 C40 120.54(16) . . ?
C41 C42 C37 120.14(17) . . ?
N4 C2 C1 112.26(19) . . ?
N1 C24 C25 113.98(19) . . ?
N1 C23 C22 115.2(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_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2009466'
loop_
_audit_author_name
_audit_author_address
'Sijing Zhang'
;Anhui University
China
;
_audit_update_record             
;
2020-06-12 deposited with the CCDC.	2020-09-23 downloaded from the CCDC.
;
_audit_creation_date             2020-01-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.13(C19 H17 N O3)'
_chemical_formula_sum            'C2.38 H2.12 N0.12 O0.38'
_chemical_formula_weight         38.42
_chemical_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   32.861(6)
_cell_length_b                   8.4446(15)
_cell_length_c                   11.602(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3219.5(10)
_cell_formula_units_Z            64
_cell_measurement_reflns_used    5864
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.015
_cell_measurement_theta_min      2.490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5191
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1246 before and 0.0521 after correction.
The Ratio of minimum to maximum transmission is 0.6963.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             1296
_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  0.0641
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23591
_diffrn_reflns_point_group_measured_fraction_full 0.907
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_min         1.239
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.669
_reflns_Friedel_fraction_full    0.803
_reflns_Friedel_fraction_max     0.703
_reflns_number_gt                4040
_reflns_number_total             6155
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Flack x determined using 1263 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.259
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         6155
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1269
_refine_ls_R_factor_gt           0.0676
_refine_ls_restrained_S_all      1.259
_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)+8.1823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2023
_refine_ls_wR_factor_ref         0.2165
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C38(H38A,H38B), C43(H43A,H43B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C15(H15), C16(H16), C19(H19), C21(H21), C22(H22), C25(H25), C26(H26),
 C27(H27), C41(H41), C23(H23), C28(H28), C31(H31), C34(H34), C36(H36), C37(H37),
  C39(H39), C40(H40), C42(H42), C44(H44)
2.c Idealised Me refined as rotating group:
 C46(H46A,H46B,H46C), C45(H45A,H45B,H45C)
2.d Idealised tetrahedral OH refined as rotating group:
 O5(H5), O4(H4), O2(H2), O1(H1)
;
_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
O5 O 0.0066(2) 1.2721(8) -0.0791(7) 0.0612(18) Uani 1 1 d . . . . .
H5 H 0.0263 1.2944 -0.0388 0.092 Uiso 1 1 calc GR . . . .
C0AA C 0.0450(3) 1.0327(11) -0.0948(8) 0.048(2) Uani 1 1 d . . . . .
N2 N 0.0945(2) 0.3400(8) -0.2751(7) 0.0490(19) Uani 1 1 d . . . . .
C5 C 0.0230(3) 0.8318(11) -0.2277(8) 0.050(2) Uani 1 1 d . . . . .
C6 C 0.1018(2) 0.1933(10) -0.3188(8) 0.044(2) Uani 1 1 d . . . . .
C7 C 0.0459(3) 0.2107(12) -0.4485(9) 0.056(3) Uani 1 1 d . . . . .
H7 H 0.0294 0.1700 -0.5065 0.068 Uiso 1 1 calc R . . . .
C8 C 0.0123(3) 1.1270(10) -0.1277(8) 0.048(2) Uani 1 1 d . . . . .
C10 C 0.0785(3) 0.1205(10) -0.4052(8) 0.046(2) Uani 1 1 d . . . . .
O4 O 0.1572(2) 0.1907(10) -0.1887(8) 0.083(3) Uani 1 1 d . . . . .
H4 H 0.1473 0.2783 -0.1773 0.124 Uiso 1 1 calc GR . . . .
C12 C 0.1353(3) 0.1133(12) -0.2719(9) 0.058(3) Uani 1 1 d . . . . .
C14 C 0.0635(3) 0.4206(10) -0.3168(8) 0.045(2) Uani 1 1 d . . . . .
C15 C -0.0144(3) 1.0736(11) -0.2089(8) 0.056(2) Uani 1 1 d . . . . .
H15 H -0.0364 1.1363 -0.2305 0.067 Uiso 1 1 calc R . . . .
C16 C 0.0286(3) 0.6783(11) -0.2846(9) 0.054(2) Uani 1 1 d . . . . .
H16 H 0.0099 0.6510 -0.3414 0.065 Uiso 1 1 calc R . . . .
O6 O 0.06983(19) 1.1004(8) -0.0149(6) 0.0614(18) Uani 1 1 d . . . . .
C19 C 0.0386(3) 0.3570(11) -0.4051(9) 0.055(2) Uani 1 1 d . . . . .
H19 H 0.0170 0.4164 -0.4337 0.066 Uiso 1 1 calc R . . . .
C21 C -0.0090(3) 0.9273(12) -0.2589(9) 0.060(3) Uani 1 1 d . . . . .
H21 H -0.0272 0.8926 -0.3146 0.072 Uiso 1 1 calc R . . . .
C22 C 0.0575(3) 0.5764(11) -0.2627(9) 0.055(2) Uani 1 1 d . . . . .
H22 H 0.0764 0.6055 -0.2068 0.066 Uiso 1 1 calc R . . . .
C25 C 0.0891(3) -0.0339(11) -0.4419(10) 0.061(3) Uani 1 1 d . . . . .
H25 H 0.0737 -0.0850 -0.4981 0.073 Uiso 1 1 calc R . . . .
C26 C 0.0501(3) 0.8857(11) -0.1434(9) 0.050(2) Uani 1 1 d . . . . .
H26 H 0.0717 0.8219 -0.1203 0.061 Uiso 1 1 calc R . . . .
C27 C 0.1453(3) -0.0340(12) -0.3089(11) 0.067(3) Uani 1 1 d . . . . .
H27 H 0.1677 -0.0864 -0.2779 0.081 Uiso 1 1 calc R . . . .
C38 C 0.1021(3) 1.0065(14) 0.0297(10) 0.073(3) Uani 1 1 d . . . . .
H38A H 0.1205 0.9761 -0.0318 0.087 Uiso 1 1 calc R . . . .
H38B H 0.0913 0.9111 0.0648 0.087 Uiso 1 1 calc R . . . .
C41 C 0.1217(3) -0.1062(12) -0.3942(10) 0.069(3) Uani 1 1 d . . . . .
H41 H 0.1287 -0.2074 -0.4190 0.083 Uiso 1 1 calc R . . . .
C46 C 0.1241(4) 1.1027(16) 0.1172(12) 0.102(5) Uani 1 1 d . . . . .
H46A H 0.1336 1.1989 0.0824 0.153 Uiso 1 1 calc GR . . . .
H46B H 0.1469 1.0436 0.1462 0.153 Uiso 1 1 calc GR . . . .
H46C H 0.1060 1.1277 0.1796 0.153 Uiso 1 1 calc GR . . . .
N1 N 0.1355(2) 0.5754(9) 0.0096(7) 0.0506(19) Uani 1 1 d . . . . .
O3 O 0.2086(2) 0.4032(10) -0.5661(6) 0.076(2) Uani 1 1 d . . . . .
O2 O 0.2637(2) 0.5903(11) -0.6493(6) 0.077(2) Uani 1 1 d . . . . .
H2 H 0.2860 0.6305 -0.6604 0.116 Uiso 1 1 calc GR . . . .
C18 C 0.1239(3) 0.5861(10) 0.1219(8) 0.048(2) Uani 1 1 d . . . . .
C20 C 0.1716(3) 0.6315(11) -0.0207(8) 0.051(2) Uani 1 1 d . . . . .
C23 C 0.1825(3) 0.6147(12) -0.1404(9) 0.054(2) Uani 1 1 d . . . . .
H23 H 0.1651 0.5553 -0.1865 0.065 Uiso 1 1 calc R . . . .
C24 C 0.2518(3) 0.6177(13) -0.5388(9) 0.058(3) Uani 1 1 d . . . . .
C28 C 0.2098(3) 0.5375(12) -0.3809(9) 0.057(3) Uani 1 1 d . . . . .
H28 H 0.1900 0.4708 -0.3505 0.068 Uiso 1 1 calc R . . . .
O1 O 0.0624(2) 0.4667(11) 0.0597(7) 0.079(2) Uani 1 1 d . . . . .
H1 H 0.0759 0.4697 0.0004 0.119 Uiso 1 1 calc GR . . . .
C30 C 0.2267(3) 0.6570(12) -0.3110(9) 0.054(2) Uani 1 1 d . . . . .
C31 C 0.2555(3) 0.7564(13) -0.3594(10) 0.063(3) Uani 1 1 d . . . . .
H31 H 0.2667 0.8375 -0.3155 0.076 Uiso 1 1 calc R . . . .
C32 C 0.2221(3) 0.5173(12) -0.4937(9) 0.058(3) Uani 1 1 d . . . . .
C33 C 0.0847(3) 0.5262(12) 0.1492(9) 0.057(3) Uani 1 1 d . . . . .
C34 C 0.2676(3) 0.7361(14) -0.4728(10) 0.067(3) Uani 1 1 d . . . . .
H34 H 0.2869 0.8043 -0.5042 0.080 Uiso 1 1 calc R . . . .
C35 C 0.1478(3) 0.6514(12) 0.2094(9) 0.058(3) Uani 1 1 d . . . . .
C36 C 0.0950(3) 0.5978(15) 0.3456(11) 0.077(3) Uani 1 1 d . . . . .
H36 H 0.0851 0.6012 0.4207 0.093 Uiso 1 1 calc R . . . .
C37 C 0.0708(3) 0.5327(13) 0.2586(10) 0.070(3) Uani 1 1 d . . . . .
H37 H 0.0451 0.4936 0.2761 0.084 Uiso 1 1 calc R . . . .
C39 C 0.2148(3) 0.6755(12) -0.1905(9) 0.057(3) Uani 1 1 d . . . . .
H39 H 0.2318 0.7367 -0.1445 0.068 Uiso 1 1 calc R . . . .
C40 C 0.1325(3) 0.6560(14) 0.3226(10) 0.076(3) Uani 1 1 d . . . . .
H40 H 0.1482 0.6990 0.3816 0.092 Uiso 1 1 calc R . . . .
C42 C 0.1975(3) 0.7008(14) 0.0616(10) 0.070(3) Uani 1 1 d . . . . .
H42 H 0.2226 0.7408 0.0390 0.084 Uiso 1 1 calc R . . . .
C43 C 0.1780(4) 0.2996(16) -0.5249(11) 0.092(4) Uani 1 1 d . . . . .
H43A H 0.1542 0.3594 -0.5014 0.110 Uiso 1 1 calc R . . . .
H43B H 0.1879 0.2405 -0.4590 0.110 Uiso 1 1 calc R . . . .
C44 C 0.1860(3) 0.7098(15) 0.1744(10) 0.075(3) Uani 1 1 d . . . . .
H44 H 0.2035 0.7545 0.2285 0.091 Uiso 1 1 calc R . . . .
C45 C 0.1674(5) 0.191(2) -0.6195(13) 0.161(9) Uani 1 1 d . . . . .
H45A H 0.1619 0.2505 -0.6881 0.241 Uiso 1 1 calc GR . . . .
H45B H 0.1438 0.1304 -0.5986 0.241 Uiso 1 1 calc GR . . . .
H45C H 0.1898 0.1200 -0.6334 0.241 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
O5 C8 1.362(10) . ?
C0AA C8 1.391(12) . ?
C0AA O6 1.361(11) . ?
C0AA C26 1.374(13) . ?
N2 C6 1.360(11) . ?
N2 C14 1.319(11) . ?
C5 C16 1.466(13) . ?
C5 C21 1.372(12) . ?
C5 C26 1.400(13) . ?
C6 C10 1.402(12) . ?
C6 C12 1.403(12) . ?
C7 C10 1.409(12) . ?
C7 C19 1.355(13) . ?
C8 C15 1.364(13) . ?
C10 C25 1.414(12) . ?
O4 C12 1.370(12) . ?
C12 C27 1.357(15) . ?
C14 C19 1.416(13) . ?
C14 C22 1.471(13) . ?
C15 C21 1.377(13) . ?
C16 C22 1.307(12) . ?
O6 C38 1.422(12) . ?
C25 C41 1.354(14) . ?
C27 C41 1.397(15) . ?
C38 C46 1.488(15) . ?
N1 C18 1.360(11) . ?
N1 C20 1.325(11) . ?
O3 C32 1.354(12) . ?
O3 C43 1.415(12) . ?
O2 C24 1.359(11) . ?
C18 C33 1.419(12) . ?
C18 C35 1.397(13) . ?
C20 C23 1.441(13) . ?
C20 C42 1.407(13) . ?
C23 C39 1.313(12) . ?
C24 C32 1.395(13) . ?
C24 C34 1.363(14) . ?
C28 C30 1.408(13) . ?
C28 C32 1.380(13) . ?
O1 C33 1.368(12) . ?
C30 C31 1.385(14) . ?
C30 C39 1.460(14) . ?
C31 C34 1.385(14) . ?
C33 C37 1.350(14) . ?
C35 C40 1.407(14) . ?
C35 C44 1.410(13) . ?
C36 C37 1.397(15) . ?
C36 C40 1.354(15) . ?
C42 C44 1.364(15) . ?
C43 C45 1.473(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
O6 C0AA C8 114.2(8) . . ?
O6 C0AA C26 125.9(8) . . ?
C26 C0AA C8 120.0(9) . . ?
C14 N2 C6 117.9(8) . . ?
C21 C5 C16 119.9(9) . . ?
C21 C5 C26 118.7(9) . . ?
C26 C5 C16 121.4(8) . . ?
N2 C6 C10 124.8(8) . . ?
N2 C6 C12 115.5(8) . . ?
C10 C6 C12 119.6(8) . . ?
C19 C7 C10 119.7(9) . . ?
O5 C8 C0AA 120.5(8) . . ?
O5 C8 C15 119.7(8) . . ?
C15 C8 C0AA 119.8(9) . . ?
C6 C10 C7 115.6(8) . . ?
C6 C10 C25 119.1(8) . . ?
C7 C10 C25 125.2(9) . . ?
O4 C12 C6 117.2(9) . . ?
C27 C12 C6 120.6(10) . . ?
C27 C12 O4 122.2(9) . . ?
N2 C14 C19 121.1(8) . . ?
N2 C14 C22 114.0(8) . . ?
C19 C14 C22 124.9(8) . . ?
C8 C15 C21 120.3(9) . . ?
C22 C16 C5 125.9(9) . . ?
C0AA O6 C38 117.4(7) . . ?
C7 C19 C14 120.8(9) . . ?
C5 C21 C15 121.0(10) . . ?
C16 C22 C14 127.0(9) . . ?
C41 C25 C10 119.1(10) . . ?
C0AA C26 C5 120.2(9) . . ?
C12 C27 C41 119.3(10) . . ?
O6 C38 C46 107.8(9) . . ?
C25 C41 C27 122.2(9) . . ?
C20 N1 C18 118.8(8) . . ?
C32 O3 C43 117.7(8) . . ?
N1 C18 C33 116.4(8) . . ?
N1 C18 C35 124.4(8) . . ?
C35 C18 C33 119.2(9) . . ?
N1 C20 C23 116.4(8) . . ?
N1 C20 C42 120.6(9) . . ?
C42 C20 C23 123.0(9) . . ?
C39 C23 C20 126.1(9) . . ?
O2 C24 C32 116.8(10) . . ?
O2 C24 C34 123.1(9) . . ?
C34 C24 C32 120.1(10) . . ?
C32 C28 C30 121.3(9) . . ?
C28 C30 C39 121.5(9) . . ?
C31 C30 C28 118.0(9) . . ?
C31 C30 C39 120.5(10) . . ?
C30 C31 C34 120.5(10) . . ?
O3 C32 C24 115.5(9) . . ?
O3 C32 C28 125.4(9) . . ?
C28 C32 C24 119.1(10) . . ?
O1 C33 C18 116.7(9) . . ?
C37 C33 C18 120.2(10) . . ?
C37 C33 O1 123.2(9) . . ?
C24 C34 C31 121.0(10) . . ?
C18 C35 C40 119.3(9) . . ?
C18 C35 C44 115.5(9) . . ?
C40 C35 C44 125.2(10) . . ?
C40 C36 C37 121.2(11) . . ?
C33 C37 C36 120.2(10) . . ?
C23 C39 C30 126.8(10) . . ?
C36 C40 C35 119.9(11) . . ?
C44 C42 C20 120.5(9) . . ?
O3 C43 C45 107.6(9) . . ?
C42 C44 C35 120.2(10) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
