# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_a
_audit_block_doi                 10.5517/ccdc.csd.cc235s58
_database_code_depnum_ccdc_archive 'CCDC 1941969'
loop_
_audit_author_name
_audit_author_address
'Liu Jianxun'
;ZhengZhou University
China
;
_audit_update_record             
;
2019-07-21 deposited with the CCDC.	2019-10-12 downloaded from the CCDC.
;
_audit_creation_date             2019-01-11
_audit_creation_method           
;
Olex2 1.2-beta
(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         'C15 H15 N O2'
_chemical_formula_sum            'C15 H15 N O2'
_chemical_formula_weight         241.28
_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'
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                   6.2682(5)
_cell_length_b                   7.1504(5)
_cell_length_c                   28.857(2)
_cell_angle_alpha                94.165(2)
_cell_angle_beta                 90.331(3)
_cell_angle_gamma                90.002(3)
_cell_volume                     1289.92(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5513
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.332
_cell_measurement_theta_min      2.831
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1629 before and 0.0700 after correction.
The Ratio of minimum to maximum transmission is 0.6592.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_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  0.0680
_diffrn_reflns_av_unetI/netI     0.0710
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            22625
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.589
_diffrn_reflns_theta_min         2.856
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_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                3413
_reflns_number_total             5963
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5963
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1179
_refine_ls_R_factor_gt           0.0591
_refine_ls_restrained_S_all      1.040
_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)+(0.0547P)²+0.3455P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1397
_refine_ls_wR_factor_ref         0.1616
_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:
 C00W(H00A,H00B), C00X(H00D,H00H)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C00A(H00C), C00E(H00E), C00F(H00F), C00G(H00G),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00P(H00P), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00Y(H00Y)
2.c Idealised Me refined as rotating group:
 C00Z(H00I,H00N,H00O), C010(H01A,H01B,H01C)
2.d Idealised tetrahedral OH refined as rotating group:
 O003(H003), O004(H004)
;
_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
O001 O 0.4987(2) 0.53436(19) 0.59857(5) 0.0467(4) Uani 1 1 d . . . . .
O002 O 0.9986(2) 0.02320(19) 0.59842(4) 0.0468(4) Uani 1 1 d . . . . .
O003 O -0.2121(2) 0.5147(2) 0.82139(5) 0.0597(4) Uani 1 1 d . . . . .
H003 H -0.142328 0.531147 0.798074 0.090 Uiso 1 1 calc GR . . . .
O004 O 0.2921(2) 0.1699(2) 0.82297(5) 0.0624(5) Uani 1 1 d . . . . .
H004 H 0.359545 0.141220 0.799254 0.094 Uiso 1 1 calc GR . . . .
N005 N 0.1201(3) 0.5940(2) 0.77303(5) 0.0401(4) Uani 1 1 d . . . . .
N006 N 0.6214(3) 0.0629(2) 0.77299(6) 0.0405(4) Uani 1 1 d . . . . .
C007 C 0.7206(3) -0.0407(3) 0.64841(7) 0.0381(5) Uani 1 1 d . . . . .
H007 H 0.651552 -0.101404 0.622970 0.046 Uiso 1 1 calc R . . . .
C008 C 0.6253(3) -0.0322(3) 0.69109(7) 0.0385(5) Uani 1 1 d . . . . .
H008 H 0.490236 -0.083556 0.694168 0.046 Uiso 1 1 calc R . . . .
C009 C 0.9192(3) 0.0404(2) 0.64266(6) 0.0350(4) Uani 1 1 d . . . . .
C00A C 0.9262(3) 0.1355(3) 0.72395(7) 0.0399(5) Uani 1 1 d . . . . .
H00C H 0.996132 0.194897 0.749448 0.048 Uiso 1 1 calc R . . . .
C00B C 0.7288(3) 0.0528(2) 0.72994(6) 0.0361(4) Uani 1 1 d . . . . .
C00C C 0.1179(3) 0.6294(3) 0.85581(7) 0.0397(5) Uani 1 1 d . . . . .
C00D C 0.2288(3) 0.5797(2) 0.73012(6) 0.0362(4) Uani 1 1 d . . . . .
C00E C 0.2207(3) 0.6272(3) 0.64861(7) 0.0388(5) Uani 1 1 d . . . . .
H00E H 0.151749 0.673615 0.623233 0.047 Uiso 1 1 calc R . . . .
C00F C 0.4264(3) 0.4940(3) 0.72421(7) 0.0397(5) Uani 1 1 d . . . . .
H00F H 0.496189 0.449368 0.749708 0.048 Uiso 1 1 calc R . . . .
C00G C 1.0209(3) 0.1308(3) 0.68061(7) 0.0391(5) Uani 1 1 d . . . . .
H00G H 1.152244 0.188320 0.677048 0.047 Uiso 1 1 calc R . . . .
C00H C 0.4190(3) 0.5427(2) 0.64290(6) 0.0353(4) Uani 1 1 d . . . . .
C00I C 0.6245(3) 0.0720(3) 0.85575(7) 0.0407(5) Uani 1 1 d . . . . .
C00J C 0.1256(3) 0.6428(3) 0.69140(7) 0.0385(5) Uani 1 1 d . . . . .
H00J H -0.009319 0.696060 0.694560 0.046 Uiso 1 1 calc R . . . .
C00K C 0.2210(3) 0.6332(3) 0.81120(7) 0.0405(5) Uani 1 1 d . . . . .
H00K H 0.364635 0.665063 0.810193 0.049 Uiso 1 1 calc R . . . .
C00L C 0.5214(3) 0.4738(3) 0.68084(7) 0.0390(5) Uani 1 1 d . . . . .
H00L H 0.652847 0.414435 0.677218 0.047 Uiso 1 1 calc R . . . .
C00M C 0.7242(3) 0.0425(3) 0.81086(7) 0.0409(5) Uani 1 1 d . . . . .
H00M H 0.867143 0.007763 0.809343 0.049 Uiso 1 1 calc R . . . .
C00N C 0.4143(3) 0.1416(3) 0.86050(7) 0.0459(5) Uani 1 1 d . . . . .
C00O C -0.0939(3) 0.5629(3) 0.85949(7) 0.0434(5) Uani 1 1 d . . . . .
C00P C 0.7398(4) 0.0403(3) 0.89589(7) 0.0497(5) Uani 1 1 d . . . . .
H00P H 0.877728 -0.006940 0.893279 0.060 Uiso 1 1 calc R . . . .
C00Q C 0.2293(4) 0.6815(3) 0.89659(7) 0.0497(5) Uani 1 1 d . . . . .
H00Q H 0.368134 0.726142 0.894795 0.060 Uiso 1 1 calc R . . . .
C00R C -0.1813(4) 0.5457(3) 0.90266(8) 0.0535(6) Uani 1 1 d . . . . .
H00R H -0.318370 0.497665 0.905087 0.064 Uiso 1 1 calc R . . . .
C00S C 0.1390(4) 0.6682(3) 0.93918(8) 0.0625(7) Uani 1 1 d . . . . .
H00S H 0.214898 0.705273 0.966074 0.075 Uiso 1 1 calc R . . . .
C00T C 0.3310(4) 0.1833(3) 0.90423(8) 0.0575(6) Uani 1 1 d . . . . .
H00T H 0.194422 0.233099 0.907482 0.069 Uiso 1 1 calc R . . . .
C00U C 0.6538(5) 0.0774(3) 0.93906(8) 0.0628(7) Uani 1 1 d . . . . .
H00U H 0.731373 0.053315 0.965542 0.075 Uiso 1 1 calc R . . . .
C00V C -0.0672(4) 0.5991(3) 0.94200(8) 0.0620(7) Uani 1 1 d . . . . .
H00V H -0.128462 0.588874 0.970983 0.074 Uiso 1 1 calc R . . . .
C00W C 0.7038(3) 0.4525(4) 0.59102(8) 0.0589(6) Uani 1 1 d . . . . .
H00A H 0.697512 0.318707 0.594474 0.071 Uiso 1 1 calc R . . . .
H00B H 0.805452 0.507933 0.613488 0.071 Uiso 1 1 calc R . . . .
C00X C 1.2038(3) 0.1005(4) 0.59074(8) 0.0584(6) Uani 1 1 d . . . . .
H00D H 1.305617 0.057814 0.613097 0.070 Uiso 1 1 calc R . . . .
H00H H 1.197581 0.236349 0.594380 0.070 Uiso 1 1 calc R . . . .
C00Y C 0.4501(5) 0.1510(3) 0.94281(9) 0.0657(7) Uani 1 1 d . . . . .
H00Y H 0.392744 0.179266 0.972138 0.079 Uiso 1 1 calc R . . . .
C00Z C 1.2710(5) 0.0380(5) 0.54267(9) 0.0959(11) Uani 1 1 d . . . . .
H00I H 1.171121 0.083286 0.520770 0.144 Uiso 1 1 calc GR . . . .
H00N H 1.275009 -0.096491 0.539280 0.144 Uiso 1 1 calc GR . . . .
H00O H 1.410312 0.086962 0.536983 0.144 Uiso 1 1 calc GR . . . .
C010 C 0.7713(5) 0.4883(5) 0.54280(9) 0.0965(11) Uani 1 1 d . . . . .
H01A H 0.669770 0.433075 0.520854 0.145 Uiso 1 1 calc GR . . . .
H01B H 0.909314 0.433883 0.536787 0.145 Uiso 1 1 calc GR . . . .
H01C H 0.778258 0.621055 0.539826 0.145 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00H 1.373(2) . ?
O001 C00W 1.424(3) . ?
O002 C009 1.370(2) . ?
O002 C00X 1.425(2) . ?
O003 H003 0.8200 . ?
O003 C00O 1.346(2) . ?
O004 H004 0.8200 . ?
O004 C00N 1.350(2) . ?
N005 C00D 1.414(2) . ?
N005 C00K 1.280(2) . ?
N006 C00B 1.414(2) . ?
N006 C00M 1.283(2) . ?
C007 H007 0.9300 . ?
C007 C008 1.370(3) . ?
C007 C009 1.389(3) . ?
C008 H008 0.9300 . ?
C008 C00B 1.393(3) . ?
C009 C00G 1.383(3) . ?
C00A H00C 0.9300 . ?
C00A C00B 1.388(3) . ?
C00A C00G 1.385(3) . ?
C00C C00K 1.446(3) . ?
C00C C00O 1.418(3) . ?
C00C C00Q 1.392(3) . ?
C00D C00F 1.388(3) . ?
C00D C00J 1.391(3) . ?
C00E H00E 0.9300 . ?
C00E C00H 1.387(3) . ?
C00E C00J 1.371(3) . ?
C00F H00F 0.9300 . ?
C00F C00L 1.387(3) . ?
C00G H00G 0.9300 . ?
C00H C00L 1.387(3) . ?
C00I C00M 1.443(3) . ?
C00I C00N 1.412(3) . ?
C00I C00P 1.394(3) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00N C00T 1.381(3) . ?
C00O C00R 1.377(3) . ?
C00P H00P 0.9300 . ?
C00P C00U 1.368(3) . ?
C00Q H00Q 0.9300 . ?
C00Q C00S 1.366(3) . ?
C00R H00R 0.9300 . ?
C00R C00V 1.369(3) . ?
C00S H00S 0.9300 . ?
C00S C00V 1.388(3) . ?
C00T H00T 0.9300 . ?
C00T C00Y 1.370(3) . ?
C00U H00U 0.9300 . ?
C00U C00Y 1.383(4) . ?
C00V H00V 0.9300 . ?
C00W H00A 0.9700 . ?
C00W H00B 0.9700 . ?
C00W C010 1.496(3) . ?
C00X H00D 0.9700 . ?
C00X H00H 0.9700 . ?
C00X C00Z 1.489(3) . ?
C00Y H00Y 0.9300 . ?
C00Z H00I 0.9600 . ?
C00Z H00N 0.9600 . ?
C00Z H00O 0.9600 . ?
C010 H01A 0.9600 . ?
C010 H01B 0.9600 . ?
C010 H01C 0.9600 . ?

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
C00H O001 C00W 117.77(15) . . ?
C009 O002 C00X 117.95(15) . . ?
C00O O003 H003 109.5 . . ?
C00N O004 H004 109.5 . . ?
C00K N005 C00D 120.82(17) . . ?
C00M N006 C00B 120.48(17) . . ?
C008 C007 H007 119.6 . . ?
C008 C007 C009 120.79(17) . . ?
C009 C007 H007 119.6 . . ?
C007 C008 H008 119.7 . . ?
C007 C008 C00B 120.55(18) . . ?
C00B C008 H008 119.7 . . ?
O002 C009 C007 115.60(16) . . ?
O002 C009 C00G 125.07(17) . . ?
C00G C009 C007 119.33(18) . . ?
C00B C00A H00C 119.5 . . ?
C00G C00A H00C 119.5 . . ?
C00G C00A C00B 121.09(17) . . ?
C008 C00B N006 118.46(17) . . ?
C00A C00B N006 122.94(16) . . ?
C00A C00B C008 118.44(17) . . ?
C00O C00C C00K 121.21(18) . . ?
C00Q C00C C00K 120.48(19) . . ?
C00Q C00C C00O 118.21(19) . . ?
C00F C00D N005 123.08(17) . . ?
C00F C00D C00J 118.58(18) . . ?
C00J C00D N005 118.18(17) . . ?
C00H C00E H00E 119.8 . . ?
C00J C00E H00E 119.8 . . ?
C00J C00E C00H 120.49(18) . . ?
C00D C00F H00F 119.5 . . ?
C00L C00F C00D 120.99(18) . . ?
C00L C00F H00F 119.5 . . ?
C009 C00G C00A 119.74(18) . . ?
C009 C00G H00G 120.1 . . ?
C00A C00G H00G 120.1 . . ?
O001 C00H C00E 115.52(16) . . ?
O001 C00H C00L 124.90(17) . . ?
C00L C00H C00E 119.58(18) . . ?
C00N C00I C00M 121.58(19) . . ?
C00P C00I C00M 119.92(19) . . ?
C00P C00I C00N 118.42(19) . . ?
C00D C00J H00J 119.6 . . ?
C00E C00J C00D 120.73(18) . . ?
C00E C00J H00J 119.6 . . ?
N005 C00K C00C 121.87(18) . . ?
N005 C00K H00K 119.1 . . ?
C00C C00K H00K 119.1 . . ?
C00F C00L H00L 120.2 . . ?
C00H C00L C00F 119.58(18) . . ?
C00H C00L H00L 120.2 . . ?
N006 C00M C00I 121.88(19) . . ?
N006 C00M H00M 119.1 . . ?
C00I C00M H00M 119.1 . . ?
O004 C00N C00I 121.32(19) . . ?
O004 C00N C00T 118.8(2) . . ?
C00T C00N C00I 119.9(2) . . ?
O003 C00O C00C 121.16(18) . . ?
O003 C00O C00R 119.0(2) . . ?
C00R C00O C00C 119.9(2) . . ?
C00I C00P H00P 119.4 . . ?
C00U C00P C00I 121.3(2) . . ?
C00U C00P H00P 119.4 . . ?
C00C C00Q H00Q 119.3 . . ?
C00S C00Q C00C 121.4(2) . . ?
C00S C00Q H00Q 119.3 . . ?
C00O C00R H00R 119.9 . . ?
C00V C00R C00O 120.2(2) . . ?
C00V C00R H00R 119.9 . . ?
C00Q C00S H00S 120.3 . . ?
C00Q C00S C00V 119.5(2) . . ?
C00V C00S H00S 120.3 . . ?
C00N C00T H00T 120.1 . . ?
C00Y C00T C00N 119.8(2) . . ?
C00Y C00T H00T 120.1 . . ?
C00P C00U H00U 120.4 . . ?
C00P C00U C00Y 119.2(2) . . ?
C00Y C00U H00U 120.4 . . ?
C00R C00V C00S 120.8(2) . . ?
C00R C00V H00V 119.6 . . ?
C00S C00V H00V 119.6 . . ?
O001 C00W H00A 110.1 . . ?
O001 C00W H00B 110.1 . . ?
O001 C00W C010 107.85(19) . . ?
H00A C00W H00B 108.4 . . ?
C010 C00W H00A 110.1 . . ?
C010 C00W H00B 110.1 . . ?
O002 C00X H00D 110.1 . . ?
O002 C00X H00H 110.1 . . ?
O002 C00X C00Z 108.18(19) . . ?
H00D C00X H00H 108.4 . . ?
C00Z C00X H00D 110.1 . . ?
C00Z C00X H00H 110.1 . . ?
C00T C00Y C00U 121.4(2) . . ?
C00T C00Y H00Y 119.3 . . ?
C00U C00Y H00Y 119.3 . . ?
C00X C00Z H00I 109.5 . . ?
C00X C00Z H00N 109.5 . . ?
C00X C00Z H00O 109.5 . . ?
H00I C00Z H00N 109.5 . . ?
H00I C00Z H00O 109.5 . . ?
H00N C00Z H00O 109.5 . . ?
C00W C010 H01A 109.5 . . ?
C00W C010 H01B 109.5 . . ?
C00W C010 H01C 109.5 . . ?
H01A C010 H01B 109.5 . . ?
H01A C010 H01C 109.5 . . ?
H01B C010 H01C 109.5 . . ?


_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_HY
_audit_block_doi                 10.5517/ccdc.csd.cc235s69
_database_code_depnum_ccdc_archive 'CCDC 1941970'
loop_
_audit_author_name
_audit_author_address
'Liu Jianxun'
;ZhengZhou University
China
;
_audit_update_record             
;
2019-07-21 deposited with the CCDC.	2019-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 N O2'
_chemical_formula_weight         255.30

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2328(2)
_cell_length_b                   7.21290(10)
_cell_length_c                   31.0245(7)
_cell_angle_alpha                92.777(2)
_cell_angle_beta                 94.558(2)
_cell_angle_gamma                90.014(2)
_cell_volume                     1388.70(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.642
_shelx_estimated_absorpt_T_min   0.877
_shelx_estimated_absorpt_T_max   0.888
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12417
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.861
_diffrn_reflns_theta_max         73.150
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             5361
_reflns_number_gt                4106
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0561P)²+0.2706P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5361
_refine_ls_number_parameters     380
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1319
_refine_ls_wR_factor_gt          0.1232
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.78276(18) 0.60103(19) 0.66548(4) 0.0704(3) Uani 1 1 d . . . . .
H1 H 0.7206 0.6232 0.6875 0.106 Uiso 1 1 calc R U . . .
O2 O 0.16395(18) 0.73252(16) 0.87553(3) 0.0626(3) Uani 1 1 d . . . . .
N1 N 0.46904(19) 0.70314(16) 0.71151(4) 0.0501(3) Uani 1 1 d . . . . .
C1 C 0.5869(3) 0.6294(3) 0.55340(6) 0.0717(5) Uani 1 1 d . . . . .
H1A H 0.6364 0.6050 0.5262 0.086 Uiso 1 1 calc R U . . .
C2 C 0.3820(3) 0.7004(3) 0.55658(6) 0.0723(5) Uani 1 1 d . . . . .
H2A H 0.2953 0.7256 0.5318 0.087 Uiso 1 1 calc R U . . .
C3 C 0.3083(3) 0.7330(2) 0.59677(5) 0.0604(4) Uani 1 1 d . . . . .
H3A H 0.1697 0.7783 0.5989 0.073 Uiso 1 1 calc R U . . .
C4 C 0.4373(2) 0.69936(19) 0.63446(5) 0.0494(3) Uani 1 1 d . . . . .
C5 C 0.6479(2) 0.6314(2) 0.63041(5) 0.0534(4) Uani 1 1 d . . . . .
C6 C 0.7183(3) 0.5945(2) 0.58971(6) 0.0642(4) Uani 1 1 d . . . . .
H6A H 0.8549 0.5458 0.5869 0.077 Uiso 1 1 calc R U . . .
C7 C 0.3518(2) 0.72463(19) 0.67635(5) 0.0500(3) Uani 1 1 d . . . . .
H7A H 0.2081 0.7573 0.6778 0.060 Uiso 1 1 calc R U . . .
C8 C 0.3788(2) 0.71065(18) 0.75206(5) 0.0463(3) Uani 1 1 d . . . . .
C9 C 0.1824(2) 0.6282(2) 0.75846(5) 0.0507(3) Uani 1 1 d . . . . .
H9A H 0.1016 0.5710 0.7350 0.061 Uiso 1 1 calc R U . . .
C10 C 0.1060(2) 0.6302(2) 0.79905(5) 0.0519(3) Uani 1 1 d . . . . .
H10A H -0.0242 0.5729 0.8030 0.062 Uiso 1 1 calc R U . . .
C11 C 0.2244(2) 0.71820(19) 0.83395(5) 0.0491(3) Uani 1 1 d . . . . .
C12 C 0.4212(2) 0.7997(2) 0.82779(5) 0.0512(3) Uani 1 1 d . . . . .
H12A H 0.5012 0.8586 0.8511 0.061 Uiso 1 1 calc R U . . .
C13 C 0.4982(2) 0.79362(19) 0.78750(5) 0.0503(3) Uani 1 1 d . . . . .
H13A H 0.6318 0.8456 0.7839 0.060 Uiso 1 1 calc R U . . .
C14 C -0.0393(3) 0.6572(3) 0.88389(6) 0.0864(6) Uani 0.5 1 d . . P A 1
H14A H -0.0270 0.5248 0.8877 0.104 Uiso 0.5 1 calc R U P A 1
H14B H -0.1445 0.6768 0.8598 0.104 Uiso 0.5 1 calc R U P A 1
C15 C -0.1094(9) 0.7556(9) 0.92505(15) 0.0781(13) Uani 0.5 1 d . . P A 1
H15A H -0.1059 0.8888 0.9221 0.094 Uiso 0.5 1 calc R U P A 1
H15B H -0.2562 0.7201 0.9292 0.094 Uiso 0.5 1 calc R U P A 1
C16 C 0.0369(10) 0.7058(11) 0.96406(15) 0.1110(19) Uani 0.5 1 d . . P A 1
H16A H -0.0100 0.7691 0.9896 0.166 Uiso 0.5 1 calc R U P A 1
H16B H 0.0317 0.5742 0.9672 0.166 Uiso 0.5 1 calc R U P A 1
H16C H 0.1818 0.7426 0.9601 0.166 Uiso 0.5 1 calc R U P A 1
C14' C -0.0393(3) 0.6572(3) 0.88389(6) 0.0864(6) Uani 0.5 1 d D . P A 2
H14C H -0.0582 0.5335 0.8704 0.104 Uiso 0.5 1 calc R U P A 2
H14D H -0.1555 0.7351 0.8726 0.104 Uiso 0.5 1 calc R U P A 2
C15' C -0.0375(13) 0.6508(10) 0.9343(2) 0.119(2) Uani 0.5 1 d D . P A 2
H15C H -0.1481 0.5679 0.9425 0.142 Uiso 0.5 1 calc R U P A 2
H15D H 0.1015 0.6117 0.9469 0.142 Uiso 0.5 1 calc R U P A 2
C16' C -0.0822(18) 0.8442(12) 0.9473(3) 0.187(4) Uani 0.5 1 d D . P A 2
H16D H -0.0848 0.8562 0.9782 0.281 Uiso 0.5 1 calc R U P A 2
H16E H 0.0282 0.9232 0.9383 0.281 Uiso 0.5 1 calc R U P A 2
H16F H -0.2193 0.8797 0.9339 0.281 Uiso 0.5 1 calc R U P A 2
O3 O 0.27666(18) 0.25873(18) 0.66369(4) 0.0731(3) Uani 1 1 d . . . . .
H3B H 0.2128 0.2354 0.6849 0.110 Uiso 1 1 d R U . . .
O4 O -0.33463(18) 0.21924(16) 0.87576(3) 0.0627(3) Uani 1 1 d . . . . .
N2 N -0.03247(19) 0.17722(16) 0.71152(4) 0.0503(3) Uani 1 1 d . . . . .
C17 C 0.0667(4) 0.1784(2) 0.55236(6) 0.0742(5) Uani 1 1 d . . . . .
H17A H 0.1116 0.1913 0.5248 0.089 Uiso 1 1 calc R U . . .
C18 C -0.1360(3) 0.1073(2) 0.55685(6) 0.0713(5) Uani 1 1 d . . . . .
H18A H -0.2253 0.0698 0.5326 0.086 Uiso 1 1 calc R U . . .
C19 C -0.2035(3) 0.0926(2) 0.59746(5) 0.0592(4) Uani 1 1 d . . . . .
H19A H -0.3406 0.0468 0.6005 0.071 Uiso 1 1 calc R U . . .
C20 C -0.0708(2) 0.14509(19) 0.63438(5) 0.0501(3) Uani 1 1 d . . . . .
C21 C 0.1383(3) 0.2115(2) 0.62920(5) 0.0551(4) Uani 1 1 d . . . . .
C22 C 0.2028(3) 0.2302(2) 0.58793(6) 0.0679(5) Uani 1 1 d . . . . .
H22A H 0.3384 0.2780 0.5843 0.081 Uiso 1 1 calc R U . . .
C23 C -0.1520(2) 0.13826(19) 0.67679(5) 0.0497(3) Uani 1 1 d . . . . .
H23A H -0.2948 0.1047 0.6788 0.060 Uiso 1 1 calc R U . . .
C24 C -0.1215(2) 0.18778(18) 0.75215(4) 0.0462(3) Uani 1 1 d . . . . .
C25 C -0.3173(2) 0.2732(2) 0.75868(5) 0.0505(3) Uani 1 1 d . . . . .
H25A H -0.3982 0.3208 0.7353 0.061 Uiso 1 1 calc R U . . .
C26 C -0.3933(2) 0.2882(2) 0.79930(5) 0.0520(3) Uani 1 1 d . . . . .
H26A H -0.5236 0.3469 0.8032 0.062 Uiso 1 1 calc R U . . .
C27 C -0.2746(2) 0.21561(19) 0.83420(5) 0.0488(3) Uani 1 1 d . . . . .
C28 C -0.0780(2) 0.1314(2) 0.82795(5) 0.0517(3) Uani 1 1 d . . . . .
H28A H 0.0020 0.0822 0.8512 0.062 Uiso 1 1 calc R U . . .
C29 C -0.0012(2) 0.12050(19) 0.78772(5) 0.0503(3) Uani 1 1 d . . . . .
H29A H 0.1326 0.0676 0.7842 0.060 Uiso 1 1 calc R U . . .
C30 C -0.5377(3) 0.2984(3) 0.88415(6) 0.0864(6) Uani 0.5 1 d D . P B 1
H30A H -0.6541 0.2166 0.8726 0.104 Uiso 0.5 1 calc R U P B 1
H30B H -0.5555 0.4171 0.8709 0.104 Uiso 0.5 1 calc R U P B 1
C31 C -0.5376(13) 0.3243(11) 0.9345(2) 0.116(2) Uani 0.5 1 d D . P B 1
H31A H -0.3992 0.3692 0.9473 0.139 Uiso 0.5 1 calc R U P B 1
H31B H -0.6488 0.4101 0.9427 0.139 Uiso 0.5 1 calc R U P B 1
C32 C -0.5818(17) 0.1363(11) 0.9477(3) 0.176(4) Uani 0.5 1 d D . P B 1
H32A H -0.5850 0.1376 0.9786 0.264 Uiso 0.5 1 calc R U P B 1
H32B H -0.7184 0.0944 0.9342 0.264 Uiso 0.5 1 calc R U P B 1
H32C H -0.4707 0.0538 0.9389 0.264 Uiso 0.5 1 calc R U P B 1
C30' C -0.5377(3) 0.2984(3) 0.88415(6) 0.0864(6) Uani 0.5 1 d . . P B 2
H30C H -0.6427 0.2702 0.8599 0.104 Uiso 0.5 1 calc R U P B 2
H30D H -0.5247 0.4322 0.8883 0.104 Uiso 0.5 1 calc R U P B 2
C31' C -0.6088(9) 0.2150(9) 0.92515(16) 0.0798(13) Uani 0.5 1 d . . P B 2
H31C H -0.7561 0.2508 0.9292 0.096 Uiso 0.5 1 calc R U P B 2
H31D H -0.6035 0.0807 0.9221 0.096 Uiso 0.5 1 calc R U P B 2
C32' C -0.4642(11) 0.2820(12) 0.96399(16) 0.116(2) Uani 0.5 1 d . . P B 2
H32D H -0.5105 0.2287 0.9895 0.174 Uiso 0.5 1 calc R U P B 2
H32E H -0.3188 0.2451 0.9601 0.174 Uiso 0.5 1 calc R U P B 2
H32F H -0.4712 0.4148 0.9672 0.174 Uiso 0.5 1 calc R U P B 2


_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 C5 1.3479(19) . ?
O1 H1 0.8200 . ?
O2 C11 1.3714(18) . ?
O2 C14' 1.426(2) . ?
O2 C14 1.426(2) . ?
N1 C7 1.2796(19) . ?
N1 C8 1.4170(18) . ?
C1 C6 1.372(3) . ?
C1 C2 1.385(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.372(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.396(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.414(2) . ?
C4 C7 1.447(2) . ?
C5 C6 1.383(2) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 C13 1.388(2) . ?
C8 C9 1.393(2) . ?
C9 C10 1.381(2) . ?
C9 H9A 0.9300 . ?
C10 C11 1.388(2) . ?
C10 H10A 0.9300 . ?
C11 C12 1.391(2) . ?
C12 C13 1.373(2) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 C15 1.525(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.514(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C14' C15' 1.565(7) . ?
C14' H14C 0.9700 . ?
C14' H14D 0.9700 . ?
C15' C16' 1.466(8) . ?
C15' H15C 0.9700 . ?
C15' H15D 0.9700 . ?
C16' H16D 0.9600 . ?
C16' H16E 0.9600 . ?
C16' H16F 0.9600 . ?
O3 C21 1.3497(19) . ?
O3 H3B 0.8198 . ?
O4 C27 1.3700(17) . ?
O4 C30' 1.426(2) . ?
O4 C30 1.426(2) . ?
N2 C23 1.2800(19) . ?
N2 C24 1.4156(18) . ?
C17 C22 1.374(3) . ?
C17 C18 1.383(3) . ?
C17 H17A 0.9300 . ?
C18 C19 1.368(2) . ?
C18 H18A 0.9300 . ?
C19 C20 1.395(2) . ?
C19 H19A 0.9300 . ?
C20 C21 1.413(2) . ?
C20 C23 1.450(2) . ?
C21 C22 1.385(2) . ?
C22 H22A 0.9300 . ?
C23 H23A 0.9300 . ?
C24 C29 1.391(2) . ?
C24 C25 1.392(2) . ?
C25 C26 1.381(2) . ?
C25 H25A 0.9300 . ?
C26 C27 1.386(2) . ?
C26 H26A 0.9300 . ?
C27 C28 1.391(2) . ?
C28 C29 1.371(2) . ?
C28 H28A 0.9300 . ?
C29 H29A 0.9300 . ?
C30 C31 1.564(6) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.467(8) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C30' C31' 1.530(6) . ?
C30' H30C 0.9700 . ?
C30' H30D 0.9700 . ?
C31' C32' 1.506(8) . ?
C31' H31C 0.9700 . ?
C31' H31D 0.9700 . ?
C32' H32D 0.9600 . ?
C32' H32E 0.9600 . ?
C32' H32F 0.9600 . ?

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
C5 O1 H1 109.5 . . ?
C11 O2 C14' 118.27(13) . . ?
C11 O2 C14 118.27(13) . . ?
C7 N1 C8 121.05(13) . . ?
C6 C1 C2 121.11(17) . . ?
C6 C1 H1A 119.4 . . ?
C2 C1 H1A 119.4 . . ?
C3 C2 C1 119.23(17) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 H2A 120.4 . . ?
C2 C3 C4 121.31(17) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C3 C4 C5 118.41(14) . . ?
C3 C4 C7 120.28(14) . . ?
C5 C4 C7 121.23(13) . . ?
O1 C5 C6 118.86(15) . . ?
O1 C5 C4 121.42(14) . . ?
C6 C5 C4 119.72(15) . . ?
C1 C6 C5 120.17(17) . . ?
C1 C6 H6A 119.9 . . ?
C5 C6 H6A 119.9 . . ?
N1 C7 C4 121.64(14) . . ?
N1 C7 H7A 119.2 . . ?
C4 C7 H7A 119.2 . . ?
C13 C8 C9 118.65(13) . . ?
C13 C8 N1 118.30(13) . . ?
C9 C8 N1 122.92(13) . . ?
C10 C9 C8 121.00(13) . . ?
C10 C9 H9A 119.5 . . ?
C8 C9 H9A 119.5 . . ?
C9 C10 C11 119.68(14) . . ?
C9 C10 H10A 120.2 . . ?
C11 C10 H10A 120.2 . . ?
O2 C11 C10 125.16(14) . . ?
O2 C11 C12 115.29(13) . . ?
C10 C11 C12 119.55(14) . . ?
C13 C12 C11 120.38(14) . . ?
C13 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C12 C13 C8 120.70(14) . . ?
C12 C13 H13A 119.6 . . ?
C8 C13 H13A 119.6 . . ?
O2 C14 C15 107.7(3) . . ?
O2 C14 H14A 110.2 . . ?
C15 C14 H14A 110.2 . . ?
O2 C14 H14B 110.2 . . ?
C15 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
C16 C15 C14 110.9(5) . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C14' C15' 106.0(3) . . ?
O2 C14' H14C 110.5 . . ?
C15' C14' H14C 110.5 . . ?
O2 C14' H14D 110.5 . . ?
C15' C14' H14D 110.5 . . ?
H14C C14' H14D 108.7 . . ?
C16' C15' C14' 102.5(7) . . ?
C16' C15' H15C 111.3 . . ?
C14' C15' H15C 111.3 . . ?
C16' C15' H15D 111.3 . . ?
C14' C15' H15D 111.3 . . ?
H15C C15' H15D 109.2 . . ?
C15' C16' H16D 109.5 . . ?
C15' C16' H16E 109.5 . . ?
H16D C16' H16E 109.5 . . ?
C15' C16' H16F 109.5 . . ?
H16D C16' H16F 109.5 . . ?
H16E C16' H16F 109.5 . . ?
C21 O3 H3B 105.2 . . ?
C27 O4 C30' 118.28(13) . . ?
C27 O4 C30 118.28(13) . . ?
C23 N2 C24 120.44(13) . . ?
C22 C17 C18 121.16(17) . . ?
C22 C17 H17A 119.4 . . ?
C18 C17 H17A 119.4 . . ?
C19 C18 C17 119.23(18) . . ?
C19 C18 H18A 120.4 . . ?
C17 C18 H18A 120.4 . . ?
C18 C19 C20 121.37(17) . . ?
C18 C19 H19A 119.3 . . ?
C20 C19 H19A 119.3 . . ?
C19 C20 C21 118.59(14) . . ?
C19 C20 C23 119.91(14) . . ?
C21 C20 C23 121.45(14) . . ?
O3 C21 C22 119.14(15) . . ?
O3 C21 C20 121.39(14) . . ?
C22 C21 C20 119.47(16) . . ?
C17 C22 C21 120.11(17) . . ?
C17 C22 H22A 119.9 . . ?
C21 C22 H22A 119.9 . . ?
N2 C23 C20 121.76(14) . . ?
N2 C23 H23A 119.1 . . ?
C20 C23 H23A 119.1 . . ?
C29 C24 C25 118.48(13) . . ?
C29 C24 N2 118.42(13) . . ?
C25 C24 N2 122.97(13) . . ?
C26 C25 C24 121.06(13) . . ?
C26 C25 H25A 119.5 . . ?
C24 C25 H25A 119.5 . . ?
C25 C26 C27 119.76(14) . . ?
C25 C26 H26A 120.1 . . ?
C27 C26 H26A 120.1 . . ?
O4 C27 C26 125.13(14) . . ?
O4 C27 C28 115.42(13) . . ?
C26 C27 C28 119.44(14) . . ?
C29 C28 C27 120.51(14) . . ?
C29 C28 H28A 119.7 . . ?
C27 C28 H28A 119.7 . . ?
C28 C29 C24 120.69(14) . . ?
C28 C29 H29A 119.7 . . ?
C24 C29 H29A 119.7 . . ?
O4 C30 C31 106.2(3) . . ?
O4 C30 H30A 110.5 . . ?
C31 C30 H30A 110.5 . . ?
O4 C30 H30B 110.5 . . ?
C31 C30 H30B 110.5 . . ?
H30A C30 H30B 108.7 . . ?
C32 C31 C30 103.1(7) . . ?
C32 C31 H31A 111.1 . . ?
C30 C31 H31A 111.1 . . ?
C32 C31 H31B 111.1 . . ?
C30 C31 H31B 111.1 . . ?
H31A C31 H31B 109.1 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O4 C30' C31' 107.5(3) . . ?
O4 C30' H30C 110.2 . . ?
C31' C30' H30C 110.2 . . ?
O4 C30' H30D 110.2 . . ?
C31' C30' H30D 110.2 . . ?
H30C C30' H30D 108.5 . . ?
C32' C31' C30' 110.3(6) . . ?
C32' C31' H31C 109.6 . . ?
C30' C31' H31C 109.6 . . ?
C32' C31' H31D 109.6 . . ?
C30' C31' H31D 109.6 . . ?
H31C C31' H31D 108.1 . . ?
C31' C32' H32D 109.5 . . ?
C31' C32' H32E 109.5 . . ?
H32D C32' H32E 109.5 . . ?
C31' C32' H32F 109.5 . . ?
H32D C32' H32F 109.5 . . ?
H32E C32' H32F 109.5 . . ?

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
C6 C1 C2 C3 -1.2(3) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C2 C3 C4 C7 -176.44(14) . . . . ?
C3 C4 C5 O1 178.11(14) . . . . ?
C7 C4 C5 O1 -5.1(2) . . . . ?
C3 C4 C5 C6 -2.1(2) . . . . ?
C7 C4 C5 C6 174.70(14) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
O1 C5 C6 C1 -178.01(15) . . . . ?
C4 C5 C6 C1 2.2(2) . . . . ?
C8 N1 C7 C4 -173.85(12) . . . . ?
C3 C4 C7 N1 -176.75(14) . . . . ?
C5 C4 C7 N1 6.5(2) . . . . ?
C7 N1 C8 C13 -142.58(14) . . . . ?
C7 N1 C8 C9 41.7(2) . . . . ?
C13 C8 C9 C10 0.7(2) . . . . ?
N1 C8 C9 C10 176.43(13) . . . . ?
C8 C9 C10 C11 1.1(2) . . . . ?
C14' O2 C11 C10 -2.2(2) . . . . ?
C14 O2 C11 C10 -2.2(2) . . . . ?
C14' O2 C11 C12 178.03(16) . . . . ?
C14 O2 C11 C12 178.03(16) . . . . ?
C9 C10 C11 O2 178.75(13) . . . . ?
C9 C10 C11 C12 -1.5(2) . . . . ?
O2 C11 C12 C13 179.88(13) . . . . ?
C10 C11 C12 C13 0.1(2) . . . . ?
C11 C12 C13 C8 1.7(2) . . . . ?
C9 C8 C13 C12 -2.1(2) . . . . ?
N1 C8 C13 C12 -178.04(13) . . . . ?
C11 O2 C14 C15 -157.1(3) . . . . ?
O2 C14 C15 C16 -67.3(5) . . . . ?
C11 O2 C14' C15' 166.6(3) . . . . ?
O2 C14' C15' C16' 78.7(7) . . . . ?
C22 C17 C18 C19 1.6(3) . . . . ?
C17 C18 C19 C20 -1.1(3) . . . . ?
C18 C19 C20 C21 -1.1(2) . . . . ?
C18 C19 C20 C23 176.30(15) . . . . ?
C19 C20 C21 O3 -177.83(14) . . . . ?
C23 C20 C21 O3 4.9(2) . . . . ?
C19 C20 C21 C22 2.7(2) . . . . ?
C23 C20 C21 C22 -174.61(14) . . . . ?
C18 C17 C22 C21 0.1(3) . . . . ?
O3 C21 C22 C17 178.27(15) . . . . ?
C20 C21 C22 C17 -2.3(2) . . . . ?
C24 N2 C23 C20 173.53(12) . . . . ?
C19 C20 C23 N2 176.80(14) . . . . ?
C21 C20 C23 N2 -5.9(2) . . . . ?
C23 N2 C24 C29 141.91(14) . . . . ?
C23 N2 C24 C25 -42.4(2) . . . . ?
C29 C24 C25 C26 -1.2(2) . . . . ?
N2 C24 C25 C26 -176.84(13) . . . . ?
C24 C25 C26 C27 -0.7(2) . . . . ?
C30' O4 C27 C26 2.0(2) . . . . ?
C30 O4 C27 C26 2.0(2) . . . . ?
C30' O4 C27 C28 -178.08(16) . . . . ?
C30 O4 C27 C28 -178.08(16) . . . . ?
C25 C26 C27 O4 -178.86(13) . . . . ?
C25 C26 C27 C28 1.2(2) . . . . ?
O4 C27 C28 C29 -179.73(13) . . . . ?
C26 C27 C28 C29 0.2(2) . . . . ?
C27 C28 C29 C24 -2.1(2) . . . . ?
C25 C24 C29 C28 2.6(2) . . . . ?
N2 C24 C29 C28 178.47(13) . . . . ?
C27 O4 C30 C31 -167.3(3) . . . . ?
O4 C30 C31 C32 -78.2(7) . . . . ?
C27 O4 C30' C31' 156.2(3) . . . . ?
O4 C30' C31' C32' 68.2(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.82 1.87 2.5975(16) 147.4 .
O3 H3B N2 0.82 1.85 2.6075(16) 152.7 .

_refine_diff_density_max         0.140
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.034



####################################################################### 
# 
# 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_20190110c6_1
_audit_block_doi                 10.5517/ccdc.csd.cc235s7b
_database_code_depnum_ccdc_archive 'CCDC 1941971'
loop_
_audit_author_name
_audit_author_address
'Liu Jianxun'
;ZhengZhou University
China
;
_audit_update_record             
;
2019-07-21 deposited with the CCDC.	2019-10-12 downloaded from the CCDC.
;
_audit_creation_date             2019-01-11
_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         '2(C17 H19 N O2)'
_chemical_formula_sum            'C34 H38 N2 O4'
_chemical_formula_weight         538.66
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     ' '
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                   6.1745(2)
_cell_length_b                   7.0411(2)
_cell_length_c                   33.2296(10)
_cell_angle_alpha                86.545(2)
_cell_angle_beta                 84.929(2)
_cell_angle_gamma                89.992(2)
_cell_volume                     1436.38(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6672
_cell_measurement_temperature    99.9(2)
_cell_measurement_theta_max      72.9700
_cell_measurement_theta_min      2.7020
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.887
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            14654
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        65.999
_diffrn_reflns_theta_max         65.999
_diffrn_reflns_theta_min         2.675
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     56.00  87.00   0.50    0.50    --    0.00  57.00 -30.00   62
  2  ω    -28.00  43.00   0.50    0.50    --    0.00  57.00 -30.00  142
  3  ω    -15.00  18.00   0.50    0.50    --    0.00  57.00  90.00   66
  4  ω     -8.00  28.00   0.50    0.50    --    0.00 -38.00  90.00   72
  5  ω    -88.00 -15.00   0.50    0.50    --    0.00 -38.00  90.00  146
  6  ω    -29.00  88.00   0.50    0.50    --    0.00  57.00-180.00  234
  7  ω     14.00  72.00   0.50    3.00    --   97.60 -82.00 120.00  116
  8  ω     29.00 148.00   0.50    3.00    --   97.60 -15.00 150.00  238
  9  ω    139.00 186.00   0.50    3.00    --   97.60  82.00 120.00   94
 10  ω     64.00 130.00   0.50    3.00    --   97.60 -82.00 -30.00  132
 11  ω     57.00 134.00   0.50    3.00    --   97.60 -82.00 150.00  154
 12  ω     55.00 126.00   0.50    3.00    --   97.60 -82.00 -90.00  142
 13  ω     65.00 186.00   0.50    3.00    --   97.60  30.00 120.00  242
 14  ω     79.00 134.00   0.50    3.00    --   97.60 -82.00  30.00  110
 15  ω     60.00 132.00   0.50    3.00    --   97.60 -82.00  60.00  144
 16  ω     48.00 134.00   0.50    3.00    --   97.60 -82.00-180.00  172
 17  ω     64.00 142.00   0.50    3.00    --   97.60  30.00   0.00  156
 18  ω     72.00 185.00   0.50    3.00    --   97.60  45.00-180.00  226
 19  ω     78.00 122.00   0.50    3.00    --   97.60 -82.00 120.00   88
 20  ω     80.00 107.00   0.50    3.00    --   97.60  45.00   0.00   54
 21  ω     45.00  71.00   0.50    3.00    --   97.60 -82.00-150.00   52
 22  ω     95.00 120.00   0.50    3.00    --   97.60 -82.00-150.00   50
 23  ω     12.00  38.00   0.50    3.00    --   97.60 -82.00-180.00   52
 24  ω      8.00 123.00   0.50    3.00    --   97.60 -30.00 150.00  230
 25  ω     89.00 116.00   0.50    3.00    --   97.60  82.00 120.00   54
 26  ω     12.00 117.00   0.50    3.00    --   97.60 -45.00   0.00  210
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0798765000
_diffrn_orient_matrix_UB_12      0.0322991000
_diffrn_orient_matrix_UB_13      0.0416870000
_diffrn_orient_matrix_UB_21      -0.1438976000
_diffrn_orient_matrix_UB_22      -0.1664303000
_diffrn_orient_matrix_UB_23      0.0190200000
_diffrn_orient_matrix_UB_31      0.1888596000
_diffrn_orient_matrix_UB_32      -0.1389565000
_diffrn_orient_matrix_UB_33      -0.0086436000
_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                4268
_reflns_number_total             4957
_reflns_odcompleteness_completeness 98.93
_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 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (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         -0.205
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         4957
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.119
_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)+(0.0396P)²+1.2218P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1306
_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:
 C21(H21A,H21B), C23(H23A,H23B), C32(H32A,H32B), C20(H20A,H20B), C28(H28A,
 H28B), C31(H31A,H31B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4A), C13(H13), C15(H15), C17(H17), C18(H18), C19(H19), C22(H22), C24(H24),
  C30(H30), C6(H6), C7(H7), C11(H11), C14(H14), C16(H16), C25(H25), C26(H26),
 C27(H27), C29(H29)
2.c Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C34(H34A,H34B,H34C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O3(H3)
;
_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 0.7067(2) 0.97948(18) 0.64764(4) 0.0230(3) Uani 1 1 d . . . . .
O4 O 1.2883(2) 0.8187(2) 0.84912(4) 0.0279(3) Uani 1 1 d . . . . .
H4 H 1.232835 0.844992 0.827971 0.042 Uiso 1 1 calc GR . . . .
N1 N 0.9840(3) 0.9227(2) 0.80290(5) 0.0216(4) Uani 1 1 d . . . . .
C2 C 0.7607(3) 0.9539(2) 0.68663(6) 0.0200(4) Uani 1 1 d . . . . .
C3 C 0.9318(3) 0.9193(2) 0.87498(6) 0.0220(4) Uani 1 1 d . . . . .
C4 C 0.9601(3) 1.0338(3) 0.69381(6) 0.0217(4) Uani 1 1 d . . . . .
H4A H 1.045296 1.096448 0.672609 0.026 Uiso 1 1 calc R . . . .
C8 C 0.9021(3) 0.9334(2) 0.76450(6) 0.0203(4) Uani 1 1 d . . . . .
C12 C 1.1433(3) 0.8492(3) 0.88087(6) 0.0233(4) Uani 1 1 d . . . . .
C13 C 1.0313(3) 1.0205(3) 0.73186(6) 0.0214(4) Uani 1 1 d . . . . .
H13 H 1.166723 1.069829 0.735980 0.026 Uiso 1 1 calc R . . . .
C15 C 0.6343(3) 0.8593(3) 0.71856(6) 0.0221(4) Uani 1 1 d . . . . .
H15 H 0.503851 0.801877 0.713974 0.027 Uiso 1 1 calc R . . . .
C17 C 0.7921(3) 0.9553(3) 0.90909(6) 0.0242(4) Uani 1 1 d . . . . .
H17 H 0.653929 1.002663 0.905624 0.029 Uiso 1 1 calc R . . . .
C18 C 0.7041(3) 0.8512(3) 0.75711(6) 0.0220(4) Uani 1 1 d . . . . .
H18 H 0.618069 0.790162 0.778419 0.026 Uiso 1 1 calc R . . . .
C19 C 1.2025(3) 0.8114(3) 0.91980(6) 0.0263(4) Uani 1 1 d . . . . .
H19 H 1.339054 0.761444 0.923724 0.032 Uiso 1 1 calc R . . . .
C21 C 0.4943(3) 0.9187(3) 0.63916(6) 0.0240(4) Uani 1 1 d . . . . .
H21A H 0.384968 0.963964 0.659069 0.029 Uiso 1 1 calc R . . . .
H21B H 0.486677 0.780889 0.640178 0.029 Uiso 1 1 calc R . . . .
C22 C 0.8573(3) 0.9456(2) 0.83503(6) 0.0219(4) Uani 1 1 d . . . . .
H22 H 0.713501 0.980049 0.832493 0.026 Uiso 1 1 calc R . . . .
C23 C 0.4544(3) 1.0001(3) 0.59745(6) 0.0257(4) Uani 1 1 d . . . . .
H23A H 0.577631 0.971898 0.578610 0.031 Uiso 1 1 calc R . . . .
H23B H 0.442002 1.137283 0.597857 0.031 Uiso 1 1 calc R . . . .
C24 C 0.8539(3) 0.9226(3) 0.94759(6) 0.0273(5) Uani 1 1 d . . . . .
H24 H 0.759841 0.950068 0.969893 0.033 Uiso 1 1 calc R . . . .
C30 C 1.0594(4) 0.8475(3) 0.95286(6) 0.0285(5) Uani 1 1 d . . . . .
H30 H 1.100622 0.821604 0.978874 0.034 Uiso 1 1 calc R . . . .
C32 C 0.2481(3) 0.9189(3) 0.58290(6) 0.0303(5) Uani 1 1 d . . . . .
H32A H 0.258910 0.781349 0.583625 0.036 Uiso 1 1 calc R . . . .
H32B H 0.124943 0.950730 0.601420 0.036 Uiso 1 1 calc R . . . .
C33 C 0.2064(4) 0.9919(4) 0.54053(7) 0.0434(6) Uani 1 1 d . . . . .
H33A H 0.322178 0.952573 0.521693 0.065 Uiso 1 1 calc GR . . . .
H33B H 0.199496 1.128338 0.539331 0.065 Uiso 1 1 calc GR . . . .
H33C H 0.070995 0.941183 0.533688 0.065 Uiso 1 1 calc GR . . . .
O2 O 0.2055(2) 0.43611(18) 0.64769(4) 0.0233(3) Uani 1 1 d . . . . .
O3 O 0.7950(2) 0.4833(2) 0.84688(4) 0.0272(3) Uani 1 1 d . . . . .
H3 H 0.735216 0.470833 0.826116 0.041 Uiso 1 1 calc GR . . . .
N2 N 0.4851(3) 0.4037(2) 0.80273(5) 0.0211(3) Uani 1 1 d . . . . .
C1 C 0.4015(3) 0.4147(2) 0.76443(6) 0.0214(4) Uani 1 1 d . . . . .
C5 C 0.4412(3) 0.3683(2) 0.87476(6) 0.0211(4) Uani 1 1 d . . . . .
C6 C 0.1334(3) 0.5152(3) 0.71857(6) 0.0218(4) Uani 1 1 d . . . . .
H6 H 0.003028 0.575645 0.714030 0.026 Uiso 1 1 calc R . . . .
C7 C 0.2039(3) 0.5005(2) 0.75721(6) 0.0216(4) Uani 1 1 d . . . . .
H7 H 0.117921 0.548632 0.778612 0.026 Uiso 1 1 calc R . . . .
C9 C 0.2595(3) 0.4388(2) 0.68672(6) 0.0212(4) Uani 1 1 d . . . . .
C10 C 0.6545(3) 0.4347(3) 0.87942(6) 0.0228(4) Uani 1 1 d . . . . .
C11 C 0.3605(3) 0.3639(2) 0.83536(6) 0.0216(4) Uani 1 1 d . . . . .
H11 H 0.215835 0.331871 0.833478 0.026 Uiso 1 1 calc R . . . .
C14 C 0.4591(3) 0.3548(3) 0.69382(6) 0.0217(4) Uani 1 1 d . . . . .
H14 H 0.544303 0.304453 0.672583 0.026 Uiso 1 1 calc R . . . .
C16 C 0.5299(3) 0.3461(3) 0.73185(6) 0.0214(4) Uani 1 1 d . . . . .
H16 H 0.665077 0.293898 0.735959 0.026 Uiso 1 1 calc R . . . .
C20 C -0.0069(3) 0.5018(3) 0.63920(6) 0.0240(4) Uani 1 1 d . . . . .
H20A H -0.014624 0.638964 0.640319 0.029 Uiso 1 1 calc R . . . .
H20B H -0.116265 0.444870 0.659052 0.029 Uiso 1 1 calc R . . . .
C25 C 0.7211(3) 0.4506(3) 0.91773(6) 0.0252(4) Uani 1 1 d . . . . .
H25 H 0.858819 0.498231 0.920750 0.030 Uiso 1 1 calc R . . . .
C26 C 0.3759(3) 0.3250(3) 0.94769(6) 0.0273(4) Uani 1 1 d . . . . .
H26 H 0.285344 0.285782 0.970529 0.033 Uiso 1 1 calc R . . . .
C27 C 0.3069(3) 0.3139(3) 0.90975(6) 0.0247(4) Uani 1 1 d . . . . .
H27 H 0.167326 0.269178 0.907203 0.030 Uiso 1 1 calc R . . . .
C28 C -0.0464(3) 0.4448(3) 0.59746(6) 0.0262(4) Uani 1 1 d . . . . .
H28A H -0.058295 0.307381 0.597759 0.031 Uiso 1 1 calc R . . . .
H28B H 0.076869 0.484221 0.578670 0.031 Uiso 1 1 calc R . . . .
C29 C 0.5836(3) 0.3958(3) 0.95158(6) 0.0277(5) Uani 1 1 d . . . . .
H29 H 0.630153 0.406368 0.977220 0.033 Uiso 1 1 calc R . . . .
C31 C -0.2526(4) 0.5339(3) 0.58290(6) 0.0306(5) Uani 1 1 d . . . . .
H31A H -0.375708 0.490941 0.601364 0.037 Uiso 1 1 calc R . . . .
H31B H -0.242276 0.670996 0.583761 0.037 Uiso 1 1 calc R . . . .
C34 C -0.2941(4) 0.4859(4) 0.54046(7) 0.0432(6) Uani 1 1 d . . . . .
H34A H -0.177894 0.535765 0.521690 0.065 Uiso 1 1 calc GR . . . .
H34B H -0.429128 0.541147 0.533595 0.065 Uiso 1 1 calc GR . . . .
H34C H -0.301564 0.350203 0.539157 0.065 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 C2 1.367(2) . ?
O1 C21 1.437(2) . ?
O4 H4 0.8200 . ?
O4 C12 1.349(2) . ?
N1 C8 1.411(2) . ?
N1 C22 1.285(3) . ?
C2 C4 1.399(3) . ?
C2 C15 1.396(3) . ?
C3 C12 1.422(3) . ?
C3 C17 1.398(3) . ?
C3 C22 1.445(3) . ?
C4 H4A 0.9300 . ?
C4 C13 1.373(3) . ?
C8 C13 1.398(3) . ?
C8 C18 1.400(3) . ?
C12 C19 1.386(3) . ?
C13 H13 0.9300 . ?
C15 H15 0.9300 . ?
C15 C18 1.385(3) . ?
C17 H17 0.9300 . ?
C17 C24 1.373(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C19 C30 1.384(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C23 1.508(3) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C32 1.525(3) . ?
C24 H24 0.9300 . ?
C24 C30 1.396(3) . ?
C30 H30 0.9300 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 C33 1.513(3) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
O2 C9 1.369(2) . ?
O2 C20 1.436(2) . ?
O3 H3 0.8200 . ?
O3 C10 1.352(2) . ?
N2 C1 1.413(2) . ?
N2 C11 1.289(2) . ?
C1 C7 1.395(3) . ?
C1 C16 1.394(3) . ?
C5 C10 1.422(3) . ?
C5 C11 1.443(3) . ?
C5 C27 1.401(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.390(3) . ?
C6 C9 1.393(3) . ?
C7 H7 0.9300 . ?
C9 C14 1.399(3) . ?
C10 C25 1.383(3) . ?
C11 H11 0.9300 . ?
C14 H14 0.9300 . ?
C14 C16 1.371(3) . ?
C16 H16 0.9300 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C28 1.507(3) . ?
C25 H25 0.9300 . ?
C25 C29 1.383(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.373(3) . ?
C26 C29 1.396(3) . ?
C27 H27 0.9300 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C31 1.523(3) . ?
C29 H29 0.9300 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 C34 1.514(3) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C21 117.74(14) . . ?
C12 O4 H4 109.5 . . ?
C22 N1 C8 120.56(17) . . ?
O1 C2 C4 114.98(16) . . ?
O1 C2 C15 125.67(17) . . ?
C15 C2 C4 119.34(17) . . ?
C12 C3 C22 121.45(18) . . ?
C17 C3 C12 118.38(18) . . ?
C17 C3 C22 120.12(18) . . ?
C2 C4 H4A 119.7 . . ?
C13 C4 C2 120.63(17) . . ?
C13 C4 H4A 119.7 . . ?
C13 C8 N1 118.20(17) . . ?
C13 C8 C18 118.55(17) . . ?
C18 C8 N1 123.14(17) . . ?
O4 C12 C3 121.11(17) . . ?
O4 C12 C19 119.19(18) . . ?
C19 C12 C3 119.70(19) . . ?
C4 C13 C8 120.63(18) . . ?
C4 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
C2 C15 H15 120.1 . . ?
C18 C15 C2 119.72(18) . . ?
C18 C15 H15 120.1 . . ?
C3 C17 H17 119.2 . . ?
C24 C17 C3 121.6(2) . . ?
C24 C17 H17 119.2 . . ?
C8 C18 H18 119.5 . . ?
C15 C18 C8 121.03(18) . . ?
C15 C18 H18 119.5 . . ?
C12 C19 H19 119.9 . . ?
C30 C19 C12 120.3(2) . . ?
C30 C19 H19 119.9 . . ?
O1 C21 H21A 110.2 . . ?
O1 C21 H21B 110.2 . . ?
O1 C21 C23 107.77(15) . . ?
H21A C21 H21B 108.5 . . ?
C23 C21 H21A 110.2 . . ?
C23 C21 H21B 110.2 . . ?
N1 C22 C3 121.89(18) . . ?
N1 C22 H22 119.1 . . ?
C3 C22 H22 119.1 . . ?
C21 C23 H23A 109.3 . . ?
C21 C23 H23B 109.3 . . ?
C21 C23 C32 111.80(16) . . ?
H23A C23 H23B 107.9 . . ?
C32 C23 H23A 109.3 . . ?
C32 C23 H23B 109.3 . . ?
C17 C24 H24 120.4 . . ?
C17 C24 C30 119.23(19) . . ?
C30 C24 H24 120.4 . . ?
C19 C30 C24 120.70(19) . . ?
C19 C30 H30 119.6 . . ?
C24 C30 H30 119.7 . . ?
C23 C32 H32A 108.9 . . ?
C23 C32 H32B 108.9 . . ?
H32A C32 H32B 107.7 . . ?
C33 C32 C23 113.45(18) . . ?
C33 C32 H32A 108.9 . . ?
C33 C32 H32B 108.9 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C9 O2 C20 117.82(15) . . ?
C10 O3 H3 109.5 . . ?
C11 N2 C1 121.10(17) . . ?
C7 C1 N2 123.32(17) . . ?
C16 C1 N2 117.96(17) . . ?
C16 C1 C7 118.61(18) . . ?
C10 C5 C11 121.41(17) . . ?
C27 C5 C10 118.11(18) . . ?
C27 C5 C11 120.43(18) . . ?
C7 C6 H6 120.3 . . ?
C7 C6 C9 119.44(18) . . ?
C9 C6 H6 120.3 . . ?
C1 C7 H7 119.4 . . ?
C6 C7 C1 121.11(18) . . ?
C6 C7 H7 119.4 . . ?
O2 C9 C6 125.56(18) . . ?
O2 C9 C14 114.95(16) . . ?
C6 C9 C14 119.48(18) . . ?
O3 C10 C5 121.13(17) . . ?
O3 C10 C25 118.90(18) . . ?
C25 C10 C5 119.96(18) . . ?
N2 C11 C5 121.29(18) . . ?
N2 C11 H11 119.4 . . ?
C5 C11 H11 119.4 . . ?
C9 C14 H14 119.8 . . ?
C16 C14 C9 120.49(18) . . ?
C16 C14 H14 119.8 . . ?
C1 C16 H16 119.6 . . ?
C14 C16 C1 120.78(18) . . ?
C14 C16 H16 119.6 . . ?
O2 C20 H20A 110.2 . . ?
O2 C20 H20B 110.2 . . ?
O2 C20 C28 107.76(16) . . ?
H20A C20 H20B 108.5 . . ?
C28 C20 H20A 110.2 . . ?
C28 C20 H20B 110.2 . . ?
C10 C25 H25 119.9 . . ?
C10 C25 C29 120.23(19) . . ?
C29 C25 H25 119.9 . . ?
C27 C26 H26 120.4 . . ?
C27 C26 C29 119.22(19) . . ?
C29 C26 H26 120.4 . . ?
C5 C27 H27 119.2 . . ?
C26 C27 C5 121.68(19) . . ?
C26 C27 H27 119.2 . . ?
C20 C28 H28A 109.2 . . ?
C20 C28 H28B 109.2 . . ?
C20 C28 C31 111.89(17) . . ?
H28A C28 H28B 107.9 . . ?
C31 C28 H28A 109.2 . . ?
C31 C28 H28B 109.2 . . ?
C25 C29 C26 120.75(19) . . ?
C25 C29 H29 119.6 . . ?
C26 C29 H29 119.6 . . ?
C28 C31 H31A 108.8 . . ?
C28 C31 H31B 108.8 . . ?
H31A C31 H31B 107.7 . . ?
C34 C31 C28 113.60(19) . . ?
C34 C31 H31A 108.8 . . ?
C34 C31 H31B 108.8 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

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
O1 C2 C4 C13 179.00(16) . . . . ?
O1 C2 C15 C18 -177.05(17) . . . . ?
O1 C21 C23 C32 171.14(16) . . . . ?
O4 C12 C19 C30 177.81(17) . . . . ?
N1 C8 C13 C4 179.65(16) . . . . ?
N1 C8 C18 C15 -177.56(17) . . . . ?
C2 O1 C21 C23 167.49(15) . . . . ?
C2 C4 C13 C8 -2.5(3) . . . . ?
C2 C15 C18 C8 -1.3(3) . . . . ?
C3 C12 C19 C30 -2.2(3) . . . . ?
C3 C17 C24 C30 -1.4(3) . . . . ?
C4 C2 C15 C18 2.2(3) . . . . ?
C8 N1 C22 C3 174.53(15) . . . . ?
C12 C3 C17 C24 -0.8(3) . . . . ?
C12 C3 C22 N1 -6.1(3) . . . . ?
C12 C19 C30 C24 0.0(3) . . . . ?
C13 C8 C18 C15 -1.5(3) . . . . ?
C15 C2 C4 C13 -0.3(3) . . . . ?
C17 C3 C12 O4 -177.42(16) . . . . ?
C17 C3 C12 C19 2.5(3) . . . . ?
C17 C3 C22 N1 176.61(17) . . . . ?
C17 C24 C30 C19 1.8(3) . . . . ?
C18 C8 C13 C4 3.4(3) . . . . ?
C21 O1 C2 C4 -173.58(15) . . . . ?
C21 O1 C2 C15 5.7(3) . . . . ?
C21 C23 C32 C33 -178.01(19) . . . . ?
C22 N1 C8 C13 141.85(18) . . . . ?
C22 N1 C8 C18 -42.1(3) . . . . ?
C22 C3 C12 O4 5.2(3) . . . . ?
C22 C3 C12 C19 -174.79(17) . . . . ?
C22 C3 C17 C24 176.62(17) . . . . ?
O2 C9 C14 C16 -179.04(16) . . . . ?
O2 C20 C28 C31 -171.25(16) . . . . ?
O3 C10 C25 C29 -177.80(17) . . . . ?
N2 C1 C7 C6 177.06(16) . . . . ?
N2 C1 C16 C14 -179.22(16) . . . . ?
C1 N2 C11 C5 -174.71(16) . . . . ?
C5 C10 C25 C29 2.3(3) . . . . ?
C6 C9 C14 C16 0.5(3) . . . . ?
C7 C1 C16 C14 -3.0(3) . . . . ?
C7 C6 C9 O2 177.08(16) . . . . ?
C7 C6 C9 C14 -2.4(3) . . . . ?
C9 O2 C20 C28 -167.51(15) . . . . ?
C9 C6 C7 C1 1.6(3) . . . . ?
C9 C14 C16 C1 2.2(3) . . . . ?
C10 C5 C11 N2 6.4(3) . . . . ?
C10 C5 C27 C26 0.5(3) . . . . ?
C10 C25 C29 C26 -0.4(3) . . . . ?
C11 N2 C1 C7 41.6(3) . . . . ?
C11 N2 C1 C16 -142.39(18) . . . . ?
C11 C5 C10 O3 -4.8(3) . . . . ?
C11 C5 C10 C25 175.11(17) . . . . ?
C11 C5 C27 C26 -176.92(17) . . . . ?
C16 C1 C7 C6 1.0(3) . . . . ?
C20 O2 C9 C6 -5.9(2) . . . . ?
C20 O2 C9 C14 173.59(15) . . . . ?
C20 C28 C31 C34 177.96(18) . . . . ?
C27 C5 C10 O3 177.74(16) . . . . ?
C27 C5 C10 C25 -2.3(3) . . . . ?
C27 C5 C11 N2 -176.25(17) . . . . ?
C27 C26 C29 C25 -1.4(3) . . . . ?
C29 C26 C27 C5 1.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.303
_oxdiff_exptl_absorpt_empirical_full_min 0.775
