# Electronic Supplementary Material (ESI) for ChemComm.
# 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_any211_0711
_database_code_depnum_ccdc_archive 'CCDC 1958314'
loop_
_audit_author_name
_audit_author_address
'Yang An'
;lanzhou university
China
;
_audit_update_record             
;
2019-10-09 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_audit_creation_date             2019-07-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C20 H22 N2 O2)'
_chemical_formula_sum            'C40 H44 N4 O4'
_chemical_formula_weight         644.79
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   18.7868(3)
_cell_length_b                   9.84896(13)
_cell_length_c                   19.3586(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.1425(17)
_cell_angle_gamma                90
_cell_volume                     3403.86(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10414
_cell_measurement_temperature    292.39(14)
_cell_measurement_theta_max      69.7460
_cell_measurement_theta_min      6.4520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24742
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.590
_diffrn_reflns_theta_max         66.590
_diffrn_reflns_theta_min         4.672
_diffrn_ambient_temperature      292.39(14)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -60.00   -1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -63.0000   90.0000 59

#__ type_ start__ end____ width___ exp.time_
  2 omega  -39.00   -3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  125.0000 -150.0000 36

#__ type_ start__ end____ width___ exp.time_
  3 omega  -70.00   15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -50.0000 -150.0000 85

#__ type_ start__ end____ width___ exp.time_
  4 omega  -86.00  -44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  -30.0000 42

#__ type_ start__ end____ width___ exp.time_
  5 omega   32.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   60.0000 91

#__ type_ start__ end____ width___ exp.time_
  6 omega   39.00  127.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000  -90.0000 88

#__ type_ start__ end____ width___ exp.time_
  7 omega    1.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000  120.0000 92

#__ type_ start__ end____ width___ exp.time_
  8 omega  -13.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -90.0000 85

#__ type_ start__ end____ width___ exp.time_
  9 omega  125.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 50

#__ type_ start__ end____ width___ exp.time_
 10 omega   34.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000   90.0000 74

#__ type_ start__ end____ width___ exp.time_
 11 omega   72.00  137.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000 -180.0000 65

#__ type_ start__ end____ width___ exp.time_
 12 omega   36.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 57

#__ type_ start__ end____ width___ exp.time_
 13 omega   78.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   38.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -150.0000 39

#__ type_ start__ end____ width___ exp.time_
 15 omega  101.00  145.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -165.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   74.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
 17 omega   34.00   60.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   79.00  146.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000 -150.0000 67

#__ type_ start__ end____ width___ exp.time_
 19 omega   36.00  146.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000   60.0000 110

#__ type_ start__ end____ width___ exp.time_
 20 omega   67.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -150.0000 37

#__ type_ start__ end____ width___ exp.time_
 21 omega   35.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 77

#__ type_ start__ end____ width___ exp.time_
 22 omega   35.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   60.0000 58

#__ type_ start__ end____ width___ exp.time_
 23 omega   79.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 24 omega   45.00   72.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 25 omega   45.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
 26 omega   44.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 27 omega   58.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
 28 omega   49.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -120.0000 40

#__ type_ start__ end____ width___ exp.time_
 29 omega   47.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
 30 omega   70.00  173.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000   90.0000 103

#__ type_ start__ end____ width___ exp.time_
 31 omega   75.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -165.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 32 omega   99.00  125.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 33 omega   60.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000   60.0000 51
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0217927000
_diffrn_orient_matrix_UB_12      0.1032965000
_diffrn_orient_matrix_UB_13      -0.0628859000
_diffrn_orient_matrix_UB_21      -0.0020056000
_diffrn_orient_matrix_UB_22      -0.1150555000
_diffrn_orient_matrix_UB_23      -0.0544967000
_diffrn_orient_matrix_UB_31      -0.0834460000
_diffrn_orient_matrix_UB_32      -0.0241850000
_diffrn_orient_matrix_UB_33      -0.0092197000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5298
_reflns_number_total             5971
_reflns_odcompleteness_completeness 99.15
_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, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         5971
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.034
_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)+(0.0529P)²+0.6645P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1040
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C30(H30A,H30B), C32(H32A,H32B), C33(H33A,H33B), C37(H37A,H37B),
 C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B), C42(H42A,H42B), C44(H44A,H44B),
  C46(H46A,H46B), C47(H47A,H47B)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C18(H18), C19(H19), C23(H23), C25(H25), C26(H26), C27(H27),
 C28(H28), C29(H29), C34(H34), C35(H35), C36(H36), C41(H41), C45(H45)
2.c Idealised Me refined as rotating group:
 C43(H43A,H43B,H43C), C48(H48A,H48B,H48C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.40181(6) 0.07544(10) 0.32946(6) 0.0545(3) Uani 1 1 d . . . . .
C2 C 0.36198(6) 0.41929(12) 0.23272(6) 0.0317(2) Uani 1 1 d . . . . .
N3 N 0.35529(6) 0.57682(11) 0.13305(5) 0.0373(2) Uani 1 1 d . . . . .
O4 O 0.40094(7) 0.16149(12) 0.43676(6) 0.0610(3) Uani 1 1 d . . . . .
N5 N 0.35194(6) 0.28055(11) 0.33212(6) 0.0403(2) Uani 1 1 d . . . . .
N6 N 0.14981(6) -0.01273(11) 0.35360(6) 0.0383(2) Uani 1 1 d . . . . .
C7 C 0.33751(6) 0.29776(12) 0.25575(7) 0.0353(3) Uani 1 1 d . . . . .
C8 C 0.41376(6) 0.50564(12) 0.28934(6) 0.0332(2) Uani 1 1 d . . . . .
C9 C 0.34911(8) 0.40760(14) 0.37073(7) 0.0447(3) Uani 1 1 d . . . . .
H9A H 0.359175 0.389949 0.422187 0.054 Uiso 1 1 calc R . . . .
H9B H 0.299810 0.448313 0.351993 0.054 Uiso 1 1 calc R . . . .
C10 C -0.00410(7) 0.06187(13) 0.35126(7) 0.0386(3) Uani 1 1 d . . . . .
N11 N -0.01643(7) 0.28449(12) 0.43229(7) 0.0513(3) Uani 1 1 d . . . . .
O12 O -0.02498(7) 0.49526(11) 0.38741(7) 0.0642(3) Uani 1 1 d . . . . .
C13 C 0.06391(7) 0.14415(13) 0.38618(6) 0.0352(3) Uani 1 1 d . . . . .
C14 C 0.33840(6) 0.44873(13) 0.15720(6) 0.0339(3) Uani 1 1 d . . . . .
C15 C 0.47198(7) 0.58116(13) 0.27809(7) 0.0393(3) Uani 1 1 d . . . . .
H15 H 0.478018 0.583197 0.232209 0.047 Uiso 1 1 calc R . . . .
C16 C 0.05477(8) 0.26400(14) 0.42178(7) 0.0418(3) Uani 1 1 d . . . . .
O17 O -0.12259(7) 0.40792(13) 0.41656(7) 0.0697(3) Uani 1 1 d . . . . .
C18 C 0.27978(7) 0.22699(14) 0.13354(8) 0.0456(3) Uani 1 1 d . . . . .
H18 H 0.254984 0.161298 0.100210 0.055 Uiso 1 1 calc R . . . .
C19 C 0.19394(7) 0.20744(14) 0.40946(7) 0.0427(3) Uani 1 1 d . . . . .
H19 H 0.241395 0.188934 0.406352 0.051 Uiso 1 1 calc R . . . .
C20 C 0.40717(7) 0.50151(12) 0.35933(7) 0.0374(3) Uani 1 1 d . . . . .
C21 C 0.13661(7) 0.11243(13) 0.38335(6) 0.0350(3) Uani 1 1 d . . . . .
C22 C 0.38687(7) 0.17125(14) 0.37177(7) 0.0423(3) Uani 1 1 d . . . . .
C23 C 0.29724(7) 0.20126(13) 0.20658(7) 0.0418(3) Uani 1 1 d . . . . .
H23 H 0.282384 0.120561 0.222935 0.050 Uiso 1 1 calc R . . . .
C24 C -0.06237(8) 0.06639(14) 0.38216(9) 0.0493(3) Uani 1 1 d . . . . .
C25 C 0.45565(8) 0.57617(14) 0.41518(7) 0.0457(3) Uani 1 1 d . . . . .
H25 H 0.449981 0.574927 0.461218 0.055 Uiso 1 1 calc R . . . .
C26 C 0.29864(7) 0.34963(14) 0.10885(7) 0.0421(3) Uani 1 1 d . . . . .
H26 H 0.284575 0.366312 0.059125 0.051 Uiso 1 1 calc R . . . .
C27 C -0.01498(7) -0.01210(14) 0.28738(7) 0.0444(3) Uani 1 1 d . . . . .
H27 H 0.022184 -0.012540 0.264956 0.053 Uiso 1 1 calc R . . . .
C28 C 0.18126(8) 0.32880(15) 0.43990(8) 0.0486(3) Uani 1 1 d . . . . .
H28 H 0.219625 0.392317 0.454896 0.058 Uiso 1 1 calc R . . . .
C29 C 0.11268(9) 0.35649(14) 0.44821(8) 0.0491(3) Uani 1 1 d . . . . .
H29 H 0.105198 0.435751 0.471135 0.059 Uiso 1 1 calc R . . . .
C30 C 0.34764(9) 0.58801(16) 0.05594(7) 0.0505(3) Uani 1 1 d . . . . .
H30A H 0.295041 0.584489 0.027605 0.061 Uiso 1 1 calc R . . . .
H30B H 0.372742 0.512135 0.041520 0.061 Uiso 1 1 calc R . . . .
C31 C -0.06007(9) 0.39777(15) 0.41215(8) 0.0508(3) Uani 1 1 d . . . . .
C32 C 0.13783(8) -0.13380(14) 0.39307(8) 0.0465(3) Uani 1 1 d . . . . .
H32A H 0.090828 -0.124933 0.403602 0.056 Uiso 1 1 calc R . . . .
H32B H 0.177774 -0.140757 0.438924 0.056 Uiso 1 1 calc R . . . .
C33 C 0.31898(9) 0.69143(14) 0.15741(8) 0.0488(3) Uani 1 1 d . . . . .
H33A H 0.324872 0.681256 0.208731 0.059 Uiso 1 1 calc R . . . .
H33B H 0.265813 0.691073 0.131014 0.059 Uiso 1 1 calc R . . . .
C34 C 0.51231(8) 0.65236(15) 0.40286(8) 0.0513(4) Uani 1 1 d . . . . .
H34 H 0.544467 0.702808 0.440323 0.062 Uiso 1 1 calc R . . . .
C35 C 0.52080(7) 0.65302(15) 0.33449(8) 0.0477(3) Uani 1 1 d . . . . .
H35 H 0.559680 0.702211 0.326355 0.057 Uiso 1 1 calc R . . . .
C36 C -0.08017(8) -0.08477(16) 0.25690(10) 0.0589(4) Uani 1 1 d . . . . .
H36 H -0.086497 -0.133558 0.214269 0.071 Uiso 1 1 calc R . . . .
C37 C 0.21937(8) -0.02244(16) 0.33548(9) 0.0515(3) Uani 1 1 d . . . . .
H37A H 0.261369 -0.027867 0.379838 0.062 Uiso 1 1 calc R . . . .
H37B H 0.225568 0.058469 0.309360 0.062 Uiso 1 1 calc R . . . .
C38 C -0.05165(10) 0.15916(16) 0.44596(10) 0.0607(4) Uani 1 1 d . . . . .
H38A H -0.099655 0.179395 0.452549 0.073 Uiso 1 1 calc R . . . .
H38B H -0.020101 0.115838 0.489819 0.073 Uiso 1 1 calc R . . . .
C39 C 0.38132(12) 0.71984(19) 0.04070(9) 0.0688(5) Uani 1 1 d . . . . .
H39A H 0.434809 0.719309 0.065644 0.083 Uiso 1 1 calc R . . . .
H39B H 0.373909 0.727007 -0.011045 0.083 Uiso 1 1 calc R . . . .
C40 C 0.35269(12) 0.82526(16) 0.14499(10) 0.0675(5) Uani 1 1 d . . . . .
H40A H 0.404931 0.828788 0.174438 0.081 Uiso 1 1 calc R . . . .
H40B H 0.326657 0.899414 0.159727 0.081 Uiso 1 1 calc R . . . .
C41 C -0.12727(8) -0.00908(17) 0.35118(12) 0.0670(5) Uani 1 1 d . . . . .
H41 H -0.165319 -0.008042 0.372485 0.080 Uiso 1 1 calc R . . . .
C42 C 0.13611(10) -0.26139(17) 0.34884(11) 0.0677(5) Uani 1 1 d . . . . .
H42A H 0.092814 -0.258907 0.305511 0.081 Uiso 1 1 calc R . . . .
H42B H 0.131345 -0.340092 0.377204 0.081 Uiso 1 1 calc R . . . .
C43 C 0.43660(10) -0.04606(17) 0.36551(11) 0.0687(5) Uani 1 1 d . . . . .
H43A H 0.445464 -0.107312 0.330486 0.103 Uiso 1 1 calc GR . . . .
H43B H 0.404226 -0.088594 0.388882 0.103 Uiso 1 1 calc GR . . . .
H43C H 0.483372 -0.023495 0.401248 0.103 Uiso 1 1 calc GR . . . .
C44 C 0.34666(13) 0.84142(18) 0.06518(10) 0.0739(5) Uani 1 1 d . . . . .
H44A H 0.294430 0.849199 0.036159 0.089 Uiso 1 1 calc R . . . .
H44B H 0.372352 0.923463 0.058561 0.089 Uiso 1 1 calc R . . . .
C45 C -0.13578(9) -0.08526(18) 0.28936(12) 0.0711(5) Uani 1 1 d . . . . .
H45 H -0.178872 -0.136697 0.269701 0.085 Uiso 1 1 calc R . . . .
C46 C 0.20686(11) -0.27445(19) 0.32704(12) 0.0773(6) Uani 1 1 d . . . . .
H46A H 0.249560 -0.289764 0.369932 0.093 Uiso 1 1 calc R . . . .
H46B H 0.202388 -0.351547 0.294781 0.093 Uiso 1 1 calc R . . . .
C47 C 0.21881(11) -0.1464(2) 0.28915(11) 0.0709(5) Uani 1 1 d . . . . .
H47A H 0.179151 -0.137563 0.243221 0.085 Uiso 1 1 calc R . . . .
H47B H 0.266091 -0.152414 0.278934 0.085 Uiso 1 1 calc R . . . .
C48 C -0.06572(11) 0.61970(18) 0.36642(12) 0.0743(5) Uani 1 1 d . . . . .
H48A H -0.109699 0.603093 0.325878 0.111 Uiso 1 1 calc GR . . . .
H48B H -0.034565 0.685052 0.352842 0.111 Uiso 1 1 calc GR . . . .
H48C H -0.080133 0.654207 0.406493 0.111 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 C22 1.3354(17) . ?
O1 C43 1.4360(18) . ?
C2 C7 1.4038(17) . ?
C2 C8 1.4856(16) . ?
C2 C14 1.4192(16) . ?
N3 C14 1.4153(16) . ?
N3 C30 1.4586(16) . ?
N3 C33 1.4705(17) . ?
O4 C22 1.2061(17) . ?
N5 C7 1.4277(16) . ?
N5 C9 1.4669(17) . ?
N5 C22 1.3657(17) . ?
N6 C21 1.4148(16) . ?
N6 C32 1.4709(17) . ?
N6 C37 1.4578(16) . ?
C7 C23 1.3904(18) . ?
C8 C15 1.3948(18) . ?
C8 C20 1.3991(17) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C20 1.4980(19) . ?
C10 C13 1.4860(17) . ?
C10 C24 1.4021(18) . ?
C10 C27 1.394(2) . ?
N11 C16 1.4285(17) . ?
N11 C31 1.3675(19) . ?
N11 C38 1.463(2) . ?
O12 C31 1.335(2) . ?
O12 C48 1.4350(19) . ?
C13 C16 1.4041(18) . ?
C13 C21 1.4187(17) . ?
C14 C26 1.3968(18) . ?
C15 H15 0.9300 . ?
C15 C35 1.3822(19) . ?
C16 C29 1.389(2) . ?
O17 C31 1.2078(19) . ?
C18 H18 0.9300 . ?
C18 C23 1.372(2) . ?
C18 C26 1.385(2) . ?
C19 H19 0.9300 . ?
C19 C21 1.3972(18) . ?
C19 C28 1.386(2) . ?
C20 C25 1.3878(19) . ?
C23 H23 0.9300 . ?
C24 C38 1.499(2) . ?
C24 C41 1.394(2) . ?
C25 H25 0.9300 . ?
C25 C34 1.382(2) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C27 C36 1.382(2) . ?
C28 H28 0.9300 . ?
C28 C29 1.374(2) . ?
C29 H29 0.9300 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C39 1.513(2) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 C42 1.515(2) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C40 1.514(2) . ?
C34 H34 0.9300 . ?
C34 C35 1.382(2) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C36 C45 1.377(3) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C37 C47 1.513(2) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C39 C44 1.508(3) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C40 C44 1.522(2) . ?
C41 H41 0.9300 . ?
C41 C45 1.379(3) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C42 C46 1.520(3) . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C45 H45 0.9300 . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C46 C47 1.510(3) . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 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
C22 O1 C43 116.21(12) . . ?
C7 C2 C8 117.24(10) . . ?
C7 C2 C14 118.25(11) . . ?
C14 C2 C8 124.45(11) . . ?
C14 N3 C30 116.40(10) . . ?
C14 N3 C33 113.84(10) . . ?
C30 N3 C33 111.25(11) . . ?
C7 N5 C9 113.64(10) . . ?
C22 N5 C7 125.36(11) . . ?
C22 N5 C9 118.25(11) . . ?
C21 N6 C32 114.85(10) . . ?
C21 N6 C37 116.04(10) . . ?
C37 N6 C32 111.43(11) . . ?
C2 C7 N5 117.05(11) . . ?
C23 C7 C2 121.84(11) . . ?
C23 C7 N5 121.01(11) . . ?
C15 C8 C2 123.73(11) . . ?
C15 C8 C20 118.48(11) . . ?
C20 C8 C2 117.57(11) . . ?
N5 C9 H9A 110.1 . . ?
N5 C9 H9B 110.1 . . ?
N5 C9 C20 107.94(10) . . ?
H9A C9 H9B 108.4 . . ?
C20 C9 H9A 110.1 . . ?
C20 C9 H9B 110.1 . . ?
C24 C10 C13 117.61(12) . . ?
C27 C10 C13 123.79(11) . . ?
C27 C10 C24 118.47(13) . . ?
C16 N11 C38 113.76(11) . . ?
C31 N11 C16 125.42(12) . . ?
C31 N11 C38 118.36(13) . . ?
C31 O12 C48 115.87(13) . . ?
C16 C13 C10 117.54(11) . . ?
C16 C13 C21 118.06(11) . . ?
C21 C13 C10 124.34(11) . . ?
N3 C14 C2 119.48(10) . . ?
C26 C14 C2 118.54(11) . . ?
C26 C14 N3 121.98(11) . . ?
C8 C15 H15 119.7 . . ?
C35 C15 C8 120.62(12) . . ?
C35 C15 H15 119.7 . . ?
C13 C16 N11 116.86(12) . . ?
C29 C16 N11 121.04(12) . . ?
C29 C16 C13 122.06(12) . . ?
C23 C18 H18 119.6 . . ?
C23 C18 C26 120.80(12) . . ?
C26 C18 H18 119.6 . . ?
C21 C19 H19 119.5 . . ?
C28 C19 H19 119.5 . . ?
C28 C19 C21 121.08(12) . . ?
C8 C20 C9 116.67(11) . . ?
C25 C20 C8 120.30(12) . . ?
C25 C20 C9 122.93(12) . . ?
N6 C21 C13 120.03(11) . . ?
C19 C21 N6 121.18(11) . . ?
C19 C21 C13 118.79(12) . . ?
O1 C22 N5 111.61(11) . . ?
O4 C22 O1 124.32(13) . . ?
O4 C22 N5 124.06(13) . . ?
C7 C23 H23 120.5 . . ?
C18 C23 C7 118.94(12) . . ?
C18 C23 H23 120.5 . . ?
C10 C24 C38 116.65(13) . . ?
C41 C24 C10 119.60(16) . . ?
C41 C24 C38 123.69(14) . . ?
C20 C25 H25 119.8 . . ?
C34 C25 C20 120.47(12) . . ?
C34 C25 H25 119.8 . . ?
C14 C26 H26 119.4 . . ?
C18 C26 C14 121.25(12) . . ?
C18 C26 H26 119.4 . . ?
C10 C27 H27 119.5 . . ?
C36 C27 C10 121.00(14) . . ?
C36 C27 H27 119.5 . . ?
C19 C28 H28 119.6 . . ?
C29 C28 C19 120.84(13) . . ?
C29 C28 H28 119.6 . . ?
C16 C29 H29 120.6 . . ?
C28 C29 C16 118.82(13) . . ?
C28 C29 H29 120.6 . . ?
N3 C30 H30A 109.5 . . ?
N3 C30 H30B 109.5 . . ?
N3 C30 C39 110.52(12) . . ?
H30A C30 H30B 108.1 . . ?
C39 C30 H30A 109.5 . . ?
C39 C30 H30B 109.5 . . ?
O12 C31 N11 111.70(13) . . ?
O17 C31 N11 123.87(15) . . ?
O17 C31 O12 124.43(14) . . ?
N6 C32 H32A 109.4 . . ?
N6 C32 H32B 109.4 . . ?
N6 C32 C42 111.01(13) . . ?
H32A C32 H32B 108.0 . . ?
C42 C32 H32A 109.4 . . ?
C42 C32 H32B 109.4 . . ?
N3 C33 H33A 109.4 . . ?
N3 C33 H33B 109.4 . . ?
N3 C33 C40 111.02(12) . . ?
H33A C33 H33B 108.0 . . ?
C40 C33 H33A 109.4 . . ?
C40 C33 H33B 109.4 . . ?
C25 C34 H34 120.2 . . ?
C35 C34 C25 119.51(12) . . ?
C35 C34 H34 120.2 . . ?
C15 C35 H35 119.7 . . ?
C34 C35 C15 120.55(13) . . ?
C34 C35 H35 119.7 . . ?
C27 C36 H36 119.9 . . ?
C45 C36 C27 120.29(17) . . ?
C45 C36 H36 119.9 . . ?
N6 C37 H37A 109.5 . . ?
N6 C37 H37B 109.5 . . ?
N6 C37 C47 110.75(13) . . ?
H37A C37 H37B 108.1 . . ?
C47 C37 H37A 109.5 . . ?
C47 C37 H37B 109.5 . . ?
N11 C38 C24 108.52(12) . . ?
N11 C38 H38A 110.0 . . ?
N11 C38 H38B 110.0 . . ?
C24 C38 H38A 110.0 . . ?
C24 C38 H38B 110.0 . . ?
H38A C38 H38B 108.4 . . ?
C30 C39 H39A 109.2 . . ?
C30 C39 H39B 109.2 . . ?
H39A C39 H39B 107.9 . . ?
C44 C39 C30 111.86(14) . . ?
C44 C39 H39A 109.2 . . ?
C44 C39 H39B 109.2 . . ?
C33 C40 H40A 109.6 . . ?
C33 C40 H40B 109.6 . . ?
C33 C40 C44 110.47(14) . . ?
H40A C40 H40B 108.1 . . ?
C44 C40 H40A 109.6 . . ?
C44 C40 H40B 109.6 . . ?
C24 C41 H41 119.6 . . ?
C45 C41 C24 120.87(15) . . ?
C45 C41 H41 119.6 . . ?
C32 C42 H42A 109.4 . . ?
C32 C42 H42B 109.4 . . ?
C32 C42 C46 111.13(14) . . ?
H42A C42 H42B 108.0 . . ?
C46 C42 H42A 109.4 . . ?
C46 C42 H42B 109.4 . . ?
O1 C43 H43A 109.5 . . ?
O1 C43 H43B 109.5 . . ?
O1 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C39 C44 C40 109.45(15) . . ?
C39 C44 H44A 109.8 . . ?
C39 C44 H44B 109.8 . . ?
C40 C44 H44A 109.8 . . ?
C40 C44 H44B 109.8 . . ?
H44A C44 H44B 108.2 . . ?
C36 C45 C41 119.66(15) . . ?
C36 C45 H45 120.2 . . ?
C41 C45 H45 120.2 . . ?
C42 C46 H46A 109.7 . . ?
C42 C46 H46B 109.7 . . ?
H46A C46 H46B 108.2 . . ?
C47 C46 C42 109.83(14) . . ?
C47 C46 H46A 109.7 . . ?
C47 C46 H46B 109.7 . . ?
C37 C47 H47A 109.4 . . ?
C37 C47 H47B 109.4 . . ?
C46 C47 C37 111.13(15) . . ?
C46 C47 H47A 109.4 . . ?
C46 C47 H47B 109.4 . . ?
H47A C47 H47B 108.0 . . ?
O12 C48 H48A 109.5 . . ?
O12 C48 H48B 109.5 . . ?
O12 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 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
C2 C7 C23 C18 -1.29(19) . . . . ?
C2 C8 C15 C35 -176.15(12) . . . . ?
C2 C8 C20 C9 1.18(16) . . . . ?
C2 C8 C20 C25 177.72(11) . . . . ?
C2 C14 C26 C18 2.49(18) . . . . ?
N3 C14 C26 C18 -177.20(12) . . . . ?
N3 C30 C39 C44 -56.68(19) . . . . ?
N3 C33 C40 C44 57.08(19) . . . . ?
N5 C7 C23 C18 175.03(12) . . . . ?
N5 C9 C20 C8 41.67(15) . . . . ?
N5 C9 C20 C25 -134.77(12) . . . . ?
N6 C32 C42 C46 55.49(18) . . . . ?
N6 C37 C47 C46 -57.41(19) . . . . ?
C7 C2 C8 C15 144.30(12) . . . . ?
C7 C2 C8 C20 -30.25(15) . . . . ?
C7 C2 C14 N3 173.11(10) . . . . ?
C7 C2 C14 C26 -6.59(16) . . . . ?
C7 N5 C9 C20 -59.89(14) . . . . ?
C7 N5 C22 O1 -4.45(18) . . . . ?
C7 N5 C22 O4 177.05(13) . . . . ?
C8 C2 C7 N5 12.23(15) . . . . ?
C8 C2 C7 C23 -171.31(11) . . . . ?
C8 C2 C14 N3 -9.65(17) . . . . ?
C8 C2 C14 C26 170.65(11) . . . . ?
C8 C15 C35 C34 -0.6(2) . . . . ?
C8 C20 C25 C34 -1.85(19) . . . . ?
C9 N5 C7 C2 33.49(15) . . . . ?
C9 N5 C7 C23 -142.99(12) . . . . ?
C9 N5 C22 O1 -164.41(11) . . . . ?
C9 N5 C22 O4 17.1(2) . . . . ?
C9 C20 C25 C34 174.47(12) . . . . ?
C10 C13 C16 N11 10.56(17) . . . . ?
C10 C13 C16 C29 -171.84(12) . . . . ?
C10 C13 C21 N6 -8.08(18) . . . . ?
C10 C13 C21 C19 171.07(12) . . . . ?
C10 C24 C38 N11 39.91(18) . . . . ?
C10 C24 C41 C45 -1.8(2) . . . . ?
C10 C27 C36 C45 0.0(2) . . . . ?
N11 C16 C29 C28 176.77(13) . . . . ?
C13 C10 C24 C38 2.58(18) . . . . ?
C13 C10 C24 C41 179.94(12) . . . . ?
C13 C10 C27 C36 -178.83(12) . . . . ?
C13 C16 C29 C28 -0.7(2) . . . . ?
C14 C2 C7 N5 -170.33(10) . . . . ?
C14 C2 C7 C23 6.13(17) . . . . ?
C14 C2 C8 C15 -32.96(18) . . . . ?
C14 C2 C8 C20 152.49(11) . . . . ?
C14 N3 C30 C39 -169.12(13) . . . . ?
C14 N3 C33 C40 166.91(12) . . . . ?
C15 C8 C20 C9 -173.66(11) . . . . ?
C15 C8 C20 C25 2.88(18) . . . . ?
C16 N11 C31 O12 -6.3(2) . . . . ?
C16 N11 C31 O17 173.94(15) . . . . ?
C16 N11 C38 C24 -59.53(17) . . . . ?
C16 C13 C21 N6 174.59(11) . . . . ?
C16 C13 C21 C19 -6.26(17) . . . . ?
C19 C28 C29 C16 -3.6(2) . . . . ?
C20 C8 C15 C35 -1.64(19) . . . . ?
C20 C25 C34 C35 -0.5(2) . . . . ?
C21 N6 C32 C42 167.29(12) . . . . ?
C21 N6 C37 C47 -167.14(13) . . . . ?
C21 C13 C16 N11 -171.93(11) . . . . ?
C21 C13 C16 C29 5.67(19) . . . . ?
C21 C19 C28 C29 2.9(2) . . . . ?
C22 N5 C7 C2 -127.27(13) . . . . ?
C22 N5 C7 C23 56.25(17) . . . . ?
C22 N5 C9 C20 102.35(13) . . . . ?
C23 C18 C26 C14 2.5(2) . . . . ?
C24 C10 C13 C16 -29.84(16) . . . . ?
C24 C10 C13 C21 152.82(12) . . . . ?
C24 C10 C27 C36 -3.0(2) . . . . ?
C24 C41 C45 C36 -1.3(2) . . . . ?
C25 C34 C35 C15 1.7(2) . . . . ?
C26 C18 C23 C7 -3.1(2) . . . . ?
C27 C10 C13 C16 145.98(13) . . . . ?
C27 C10 C13 C21 -31.36(19) . . . . ?
C27 C10 C24 C38 -173.46(13) . . . . ?
C27 C10 C24 C41 3.89(19) . . . . ?
C27 C36 C45 C41 2.2(2) . . . . ?
C28 C19 C21 N6 -178.70(12) . . . . ?
C28 C19 C21 C13 2.16(19) . . . . ?
C30 N3 C14 C2 164.26(11) . . . . ?
C30 N3 C14 C26 -16.05(17) . . . . ?
C30 N3 C33 C40 -59.19(16) . . . . ?
C30 C39 C44 C40 54.5(2) . . . . ?
C31 N11 C16 C13 -127.07(15) . . . . ?
C31 N11 C16 C29 55.3(2) . . . . ?
C31 N11 C38 C24 103.64(15) . . . . ?
C32 N6 C21 C13 -63.00(15) . . . . ?
C32 N6 C21 C19 117.87(13) . . . . ?
C32 N6 C37 C47 58.90(17) . . . . ?
C32 C42 C46 C47 -53.6(2) . . . . ?
C33 N3 C14 C2 -64.31(14) . . . . ?
C33 N3 C14 C26 115.38(13) . . . . ?
C33 N3 C30 C39 58.25(16) . . . . ?
C33 C40 C44 C39 -54.3(2) . . . . ?
C37 N6 C21 C13 164.59(12) . . . . ?
C37 N6 C21 C19 -14.54(17) . . . . ?
C37 N6 C32 C42 -58.16(15) . . . . ?
C38 N11 C16 C13 34.72(18) . . . . ?
C38 N11 C16 C29 -142.91(14) . . . . ?
C38 N11 C31 O12 -167.30(13) . . . . ?
C38 N11 C31 O17 12.9(2) . . . . ?
C38 C24 C41 C45 175.38(15) . . . . ?
C41 C24 C38 N11 -137.33(15) . . . . ?
C42 C46 C47 C37 54.5(2) . . . . ?
C43 O1 C22 O4 0.3(2) . . . . ?
C43 O1 C22 N5 -178.19(13) . . . . ?
C48 O12 C31 N11 -178.63(15) . . . . ?
C48 O12 C31 O17 1.2(2) . . . . ?

_olex2_date_sample_data_collection 2019-07-11
_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_any_224
_database_code_depnum_ccdc_archive 'CCDC 1958315'
loop_
_audit_author_name
_audit_author_address
'Yang An'
;lanzhou university
China
;
_audit_update_record             
;
2019-10-09 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_audit_creation_date             2019-07-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 Cl N2 O3'
_chemical_formula_sum            'C19 H19 Cl N2 O3'
_chemical_formula_weight         358.81
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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'
Cl Cl 0.3639 0.7018 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.3251(3)
_cell_length_b                   18.1174(6)
_cell_length_c                   10.1704(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.755(3)
_cell_angle_gamma                90
_cell_volume                     1698.25(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2059
_cell_measurement_temperature    292.26(11)
_cell_measurement_theta_max      69.2520
_cell_measurement_theta_min      9.6520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.171
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5745
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        66.593
_diffrn_reflns_theta_max         66.593
_diffrn_reflns_theta_min         4.882
_diffrn_ambient_temperature      292.26(11)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -2.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  150.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega   33.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  150.0000 30

#__ type_ start__ end____ width___ exp.time_
  3 omega  -87.00  -54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  120.0000 33

#__ type_ start__ end____ width___ exp.time_
  4 omega  -80.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
  5 omega   65.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 57

#__ type_ start__ end____ width___ exp.time_
  6 omega   68.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -30.0000 57

#__ type_ start__ end____ width___ exp.time_
  7 omega   72.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -120.0000 40

#__ type_ start__ end____ width___ exp.time_
  8 omega   24.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega  100.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 76

#__ type_ start__ end____ width___ exp.time_
 10 omega   43.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  120.0000 39

#__ type_ start__ end____ width___ exp.time_
 11 omega   61.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 40

#__ type_ start__ end____ width___ exp.time_
 12 omega   64.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 50

#__ type_ start__ end____ width___ exp.time_
 13 omega   54.00  132.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  -60.0000 78

#__ type_ start__ end____ width___ exp.time_
 14 omega   52.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 41

#__ type_ start__ end____ width___ exp.time_
 15 omega  109.00  150.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 16 omega   88.00  161.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 73

#__ type_ start__ end____ width___ exp.time_
 17 omega   49.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 18 omega  130.00  155.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 19 omega   37.00   79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -180.0000 42
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0734156000
_diffrn_orient_matrix_UB_12      0.0716139000
_diffrn_orient_matrix_UB_13      -0.0371253000
_diffrn_orient_matrix_UB_21      0.0478316000
_diffrn_orient_matrix_UB_22      0.0168615000
_diffrn_orient_matrix_UB_23      0.1486675000
_diffrn_orient_matrix_UB_31      0.1423653000
_diffrn_orient_matrix_UB_32      -0.0425996000
_diffrn_orient_matrix_UB_33      -0.0034429000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2415
_reflns_number_total             2913
_reflns_odcompleteness_completeness 96.92
_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, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2913
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.056
_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)+(0.0557P)²+0.3727P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1177
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C12(H12)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.60309(6) 0.15008(3) 0.53336(7) 0.04961(19) Uani 1 1 d . . . . .
O1 O 0.67060(18) -0.20276(8) 0.7430(2) 0.0532(5) Uani 1 1 d . . . . .
O2 O 0.59774(16) -0.08605(8) 0.76993(17) 0.0438(4) Uani 1 1 d . . . . .
O3 O 1.40070(16) 0.17214(9) 0.82118(19) 0.0483(4) Uani 1 1 d . . . . .
N1 N 0.79933(19) -0.10570(9) 0.6788(2) 0.0362(4) Uani 1 1 d . . . . .
N2 N 1.12340(17) 0.10490(8) 0.76765(18) 0.0302(4) Uani 1 1 d . . . . .
C1 C 0.9310(2) -0.15020(11) 0.6786(3) 0.0414(5) Uani 1 1 d . . . . .
H1A H 0.971404 -0.141498 0.597579 0.050 Uiso 1 1 calc R . . . .
H1B H 0.908279 -0.202284 0.683445 0.050 Uiso 1 1 calc R . . . .
C2 C 1.0382(2) -0.12766(11) 0.7982(2) 0.0347(5) Uani 1 1 d . . . . .
C3 C 1.1111(3) -0.17840(12) 0.8864(3) 0.0453(6) Uani 1 1 d . . . . .
H3 H 1.099925 -0.228680 0.869402 0.054 Uiso 1 1 calc R . . . .
C4 C 1.2002(3) -0.15437(13) 0.9993(3) 0.0473(6) Uani 1 1 d . . . . .
H4 H 1.250169 -0.188343 1.057773 0.057 Uiso 1 1 calc R . . . .
C5 C 1.2148(2) -0.07980(13) 1.0250(2) 0.0400(5) Uani 1 1 d . . . . .
H5 H 1.274137 -0.063706 1.101485 0.048 Uiso 1 1 calc R . . . .
C6 C 1.1422(2) -0.02879(11) 0.9385(2) 0.0331(4) Uani 1 1 d . . . . .
H6 H 1.152511 0.021317 0.957531 0.040 Uiso 1 1 calc R . . . .
C7 C 1.0533(2) -0.05181(10) 0.8226(2) 0.0289(4) Uani 1 1 d . . . . .
C8 C 0.9585(2) -0.00067(10) 0.73334(19) 0.0272(4) Uani 1 1 d . . . . .
C9 C 0.8235(2) -0.02831(11) 0.6732(2) 0.0306(4) Uani 1 1 d . . . . .
C10 C 0.7150(2) 0.01700(11) 0.6081(2) 0.0342(4) Uani 1 1 d . . . . .
H10 H 0.626769 -0.002481 0.568005 0.041 Uiso 1 1 calc R . . . .
C11 C 0.7421(2) 0.09140(11) 0.6047(2) 0.0333(4) Uani 1 1 d . . . . .
C12 C 0.8755(2) 0.12145(11) 0.6546(2) 0.0323(4) Uani 1 1 d . . . . .
H12 H 0.891458 0.171855 0.647339 0.039 Uiso 1 1 calc R . . . .
C13 C 0.9861(2) 0.07560(10) 0.71589(19) 0.0280(4) Uani 1 1 d . . . . .
C14 C 1.1372(2) 0.18458(11) 0.7825(2) 0.0388(5) Uani 1 1 d . . . . .
H14A H 1.056417 0.204080 0.821553 0.047 Uiso 1 1 calc R . . . .
H14B H 1.136438 0.207487 0.696227 0.047 Uiso 1 1 calc R . . . .
C15 C 1.2789(2) 0.20137(13) 0.8719(3) 0.0473(6) Uani 1 1 d . . . . .
H15A H 1.289876 0.254428 0.881357 0.057 Uiso 1 1 calc R . . . .
H15B H 1.275757 0.180801 0.959425 0.057 Uiso 1 1 calc R . . . .
C16 C 1.3857(2) 0.09448(12) 0.8022(3) 0.0425(5) Uani 1 1 d . . . . .
H16A H 1.386118 0.070707 0.887684 0.051 Uiso 1 1 calc R . . . .
H16B H 1.467824 0.075884 0.764070 0.051 Uiso 1 1 calc R . . . .
C17 C 1.2472(2) 0.07511(11) 0.7117(2) 0.0348(5) Uani 1 1 d . . . . .
H17A H 1.248882 0.095752 0.623919 0.042 Uiso 1 1 calc R . . . .
H17B H 1.238329 0.021916 0.703097 0.042 Uiso 1 1 calc R . . . .
C18 C 0.6870(2) -0.13727(11) 0.7319(2) 0.0344(5) Uani 1 1 d . . . . .
C19 C 0.4720(3) -0.11444(14) 0.8205(3) 0.0513(6) Uani 1 1 d . . . . .
H19A H 0.407998 -0.137606 0.749591 0.077 Uiso 1 1 calc GR . . . .
H19B H 0.422216 -0.074595 0.856429 0.077 Uiso 1 1 calc GR . . . .
H19C H 0.502224 -0.149988 0.889159 0.077 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
Cl1 C11 1.746(2) . ?
O1 C18 1.204(2) . ?
O2 C18 1.342(2) . ?
O2 C19 1.445(3) . ?
O3 C15 1.419(3) . ?
O3 C16 1.424(3) . ?
N1 C1 1.469(3) . ?
N1 C9 1.423(2) . ?
N1 C18 1.374(3) . ?
N2 C13 1.411(2) . ?
N2 C14 1.455(2) . ?
N2 C17 1.466(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.509(3) . ?
C2 C3 1.387(3) . ?
C2 C7 1.399(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.398(3) . ?
C7 C8 1.490(3) . ?
C8 C9 1.406(3) . ?
C8 C13 1.422(3) . ?
C9 C10 1.390(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.373(3) . ?
C11 C12 1.382(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.396(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.516(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.509(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C18 O2 C19 115.39(17) . . ?
C15 O3 C16 110.50(16) . . ?
C9 N1 C1 113.80(16) . . ?
C18 N1 C1 117.35(17) . . ?
C18 N1 C9 124.10(17) . . ?
C13 N2 C14 118.22(16) . . ?
C13 N2 C17 116.09(16) . . ?
C14 N2 C17 110.08(16) . . ?
N1 C1 H1A 110.2 . . ?
N1 C1 H1B 110.2 . . ?
N1 C1 C2 107.57(17) . . ?
H1A C1 H1B 108.5 . . ?
C2 C1 H1A 110.2 . . ?
C2 C1 H1B 110.2 . . ?
C3 C2 C1 122.7(2) . . ?
C3 C2 C7 120.7(2) . . ?
C7 C2 C1 116.40(19) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.7(2) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.5(2) . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C8 117.95(19) . . ?
C6 C7 C2 118.22(19) . . ?
C6 C7 C8 123.30(18) . . ?
C9 C8 C7 116.91(17) . . ?
C9 C8 C13 117.35(17) . . ?
C13 C8 C7 125.35(17) . . ?
C8 C9 N1 118.06(18) . . ?
C10 C9 N1 119.54(18) . . ?
C10 C9 C8 122.40(18) . . ?
C9 C10 H10 121.0 . . ?
C11 C10 C9 117.93(19) . . ?
C11 C10 H10 121.0 . . ?
C10 C11 Cl1 118.71(16) . . ?
C10 C11 C12 122.44(19) . . ?
C12 C11 Cl1 118.85(16) . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.52(18) . . ?
C13 C12 H12 120.2 . . ?
N2 C13 C8 119.37(17) . . ?
C12 C13 N2 120.63(17) . . ?
C12 C13 C8 119.91(18) . . ?
N2 C14 H14A 110.0 . . ?
N2 C14 H14B 110.0 . . ?
N2 C14 C15 108.46(18) . . ?
H14A C14 H14B 108.4 . . ?
C15 C14 H14A 110.0 . . ?
C15 C14 H14B 110.0 . . ?
O3 C15 C14 112.3(2) . . ?
O3 C15 H15A 109.1 . . ?
O3 C15 H15B 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
O3 C16 H16A 109.3 . . ?
O3 C16 H16B 109.3 . . ?
O3 C16 C17 111.72(18) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
N2 C17 C16 109.20(17) . . ?
N2 C17 H17A 109.8 . . ?
N2 C17 H17B 109.8 . . ?
C16 C17 H17A 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
O1 C18 O2 124.2(2) . . ?
O1 C18 N1 124.21(19) . . ?
O2 C18 N1 111.63(17) . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
Cl1 C11 C12 C13 177.85(15) . . . . ?
O3 C16 C17 N2 -57.5(2) . . . . ?
N1 C1 C2 C3 131.1(2) . . . . ?
N1 C1 C2 C7 -44.2(2) . . . . ?
N1 C9 C10 C11 179.99(18) . . . . ?
N2 C14 C15 O3 58.0(3) . . . . ?
C1 N1 C9 C8 -31.7(3) . . . . ?
C1 N1 C9 C10 147.6(2) . . . . ?
C1 N1 C18 O1 -22.0(3) . . . . ?
C1 N1 C18 O2 158.01(19) . . . . ?
C1 C2 C3 C4 -175.4(2) . . . . ?
C1 C2 C7 C6 174.68(18) . . . . ?
C1 C2 C7 C8 2.7(3) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C2 C7 C8 C9 27.6(3) . . . . ?
C2 C7 C8 C13 -159.81(18) . . . . ?
C3 C2 C7 C6 -0.7(3) . . . . ?
C3 C2 C7 C8 -172.62(18) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
C5 C6 C7 C2 1.1(3) . . . . ?
C5 C6 C7 C8 172.54(18) . . . . ?
C6 C7 C8 C9 -143.85(19) . . . . ?
C6 C7 C8 C13 28.7(3) . . . . ?
C7 C2 C3 C4 -0.3(3) . . . . ?
C7 C8 C9 N1 -12.8(3) . . . . ?
C7 C8 C9 C10 167.99(18) . . . . ?
C7 C8 C13 N2 11.2(3) . . . . ?
C7 C8 C13 C12 -165.24(18) . . . . ?
C8 C9 C10 C11 -0.8(3) . . . . ?
C9 N1 C1 C2 59.3(2) . . . . ?
C9 N1 C18 O1 -176.0(2) . . . . ?
C9 N1 C18 O2 4.0(3) . . . . ?
C9 C8 C13 N2 -176.24(17) . . . . ?
C9 C8 C13 C12 7.3(3) . . . . ?
C9 C10 C11 Cl1 -175.69(15) . . . . ?
C9 C10 C11 C12 4.9(3) . . . . ?
C10 C11 C12 C13 -2.7(3) . . . . ?
C11 C12 C13 N2 179.99(18) . . . . ?
C11 C12 C13 C8 -3.6(3) . . . . ?
C13 N2 C14 C15 165.03(18) . . . . ?
C13 N2 C17 C16 -163.64(17) . . . . ?
C13 C8 C9 N1 174.08(17) . . . . ?
C13 C8 C9 C10 -5.2(3) . . . . ?
C14 N2 C13 C8 -162.96(18) . . . . ?
C14 N2 C13 C12 13.5(3) . . . . ?
C14 N2 C17 C16 58.7(2) . . . . ?
C15 O3 C16 C17 56.6(3) . . . . ?
C16 O3 C15 C14 -57.0(3) . . . . ?
C17 N2 C13 C8 62.9(2) . . . . ?
C17 N2 C13 C12 -120.7(2) . . . . ?
C17 N2 C14 C15 -58.3(2) . . . . ?
C18 N1 C1 C2 -97.4(2) . . . . ?
C18 N1 C9 C8 123.2(2) . . . . ?
C18 N1 C9 C10 -57.6(3) . . . . ?
C19 O2 C18 O1 -3.1(3) . . . . ?
C19 O2 C18 N1 176.8(2) . . . . ?

_olex2_date_sample_data_collection 2019-07-17
_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_anyang_ay223
_database_code_depnum_ccdc_archive 'CCDC 1958317'
loop_
_audit_author_name
_audit_author_address
'Yang An'
;lanzhou university
China
;
_audit_update_record             
;
2019-10-09 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_audit_creation_date             2019-10-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H22 N2 O3'
_chemical_formula_sum            'C20 H22 N2 O3'
_chemical_formula_weight         338.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   9.4110(5)
_cell_length_b                   9.7287(5)
_cell_length_c                   9.9501(6)
_cell_angle_alpha                87.849(4)
_cell_angle_beta                 85.541(5)
_cell_angle_gamma                72.201(5)
_cell_volume                     864.67(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2736
_cell_measurement_temperature    292.49(10)
_cell_measurement_theta_max      69.4280
_cell_measurement_theta_min      4.4540
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0129
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5442
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        66.599
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_min         4.458
_diffrn_ambient_temperature      292.49(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -79.00  -51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -77.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
  2 omega  -87.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000 -120.0000 52

#__ type_ start__ end____ width___ exp.time_
  3 omega  -15.00   23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -77.0000  -90.0000 38

#__ type_ start__ end____ width___ exp.time_
  4 omega  -86.00  -60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega  -61.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega   35.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -90.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega   36.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   60.0000 51

#__ type_ start__ end____ width___ exp.time_
  8 omega  -14.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -90.0000 41

#__ type_ start__ end____ width___ exp.time_
  9 omega   50.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -63.0000  114.0565 27

#__ type_ start__ end____ width___ exp.time_
 10 omega   88.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   -7.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -63.0000  114.0565 54

#__ type_ start__ end____ width___ exp.time_
 12 omega   94.00  126.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000    0.0000 32

#__ type_ start__ end____ width___ exp.time_
 13 omega   45.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -120.0000 52

#__ type_ start__ end____ width___ exp.time_
 14 omega   55.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  120.0000 38

#__ type_ start__ end____ width___ exp.time_
 15 omega   59.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 16 omega   53.00   96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 43

#__ type_ start__ end____ width___ exp.time_
 17 omega   35.00   84.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   60.0000 49

#__ type_ start__ end____ width___ exp.time_
 18 omega   68.00  138.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000  120.0000 70

#__ type_ start__ end____ width___ exp.time_
 19 omega   37.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000  -30.0000 33

#__ type_ start__ end____ width___ exp.time_
 20 omega   87.00  171.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
 21 omega   53.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 47

#__ type_ start__ end____ width___ exp.time_
 22 omega   78.00  169.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000  -30.0000 91

#__ type_ start__ end____ width___ exp.time_
 23 omega   54.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 60

#__ type_ start__ end____ width___ exp.time_
 24 omega   87.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
 25 omega   36.00   64.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -150.0000 28

#__ type_ start__ end____ width___ exp.time_
 26 omega   59.00   84.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 27 omega   36.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 34

#__ type_ start__ end____ width___ exp.time_
 28 omega   47.00  126.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  120.0000 79

#__ type_ start__ end____ width___ exp.time_
 29 omega   69.00  133.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -90.0000 64

#__ type_ start__ end____ width___ exp.time_
 30 omega  -87.00  -62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 31 omega   69.00   95.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 32 omega  -78.00   13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -57.0000  -60.0000 91

#__ type_ start__ end____ width___ exp.time_
 33 omega  -87.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000   30.0000 53

#__ type_ start__ end____ width___ exp.time_
 34 omega  -79.00   23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -77.0000  120.0000 102

#__ type_ start__ end____ width___ exp.time_
 35 omega   32.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  120.0000 76
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0942314000
_diffrn_orient_matrix_UB_12      -0.1205801000
_diffrn_orient_matrix_UB_13      -0.0950207000
_diffrn_orient_matrix_UB_21      -0.1218562000
_diffrn_orient_matrix_UB_22      0.0450647000
_diffrn_orient_matrix_UB_23      -0.1018025000
_diffrn_orient_matrix_UB_31      0.0772971000
_diffrn_orient_matrix_UB_32      0.1053362000
_diffrn_orient_matrix_UB_33      -0.0687747000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2599
_reflns_number_total             2933
_reflns_odcompleteness_completeness 95.54
_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, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2933
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.092
_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)+(0.0587P)²+0.1253P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1128
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C20(H20A,H20B), C21(H21A,H21B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C13(H13), C18(H18), C19(H19), C22(H22)
2.c Idealised Me refined as rotating group:
 C0AA(H0AA,H0AB,H0AC), C1AA(H1AA,H1AB,H1AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.03175(14) 0.03019(13) 0.73225(12) 0.0335(3) Uani 1 1 d . . . . .
C2 C 0.04012(15) -0.11659(14) 0.75803(13) 0.0350(3) Uani 1 1 d . . . . .
O3 O 0.35377(12) 0.19688(12) 0.69667(12) 0.0530(3) Uani 1 1 d . . . . .
N4 N -0.08404(13) -0.15036(12) 0.82392(12) 0.0392(3) Uani 1 1 d . . . . .
N5 N 0.13593(13) 0.20415(12) 0.61551(12) 0.0408(3) Uani 1 1 d . . . . .
C6 C 0.28226(16) -0.05197(16) 0.61884(14) 0.0428(3) Uani 1 1 d . . . . .
H6 H 0.361008 -0.030314 0.569593 0.051 Uiso 1 1 calc R . . . .
C7 C 0.15327(15) 0.05750(14) 0.65635(13) 0.0367(3) Uani 1 1 d . . . . .
O8 O -0.32780(14) -0.25435(13) 0.90834(14) 0.0627(3) Uani 1 1 d . . . . .
O9 O 0.20156(14) 0.40978(12) 0.62597(15) 0.0682(4) Uani 1 1 d . . . . .
C10 C 0.17125(16) -0.22435(14) 0.72038(14) 0.0406(3) Uani 1 1 d . . . . .
H10 H 0.177021 -0.320083 0.739799 0.049 Uiso 1 1 calc R . . . .
C11 C -0.09097(14) 0.15661(13) 0.78483(13) 0.0351(3) Uani 1 1 d . . . . .
C12 C 0.29401(16) -0.19379(15) 0.65470(14) 0.0430(3) Uani 1 1 d . . . . .
C13 C -0.17378(15) 0.15628(15) 0.90761(14) 0.0398(3) Uani 1 1 d . . . . .
H13 H -0.155501 0.072161 0.959796 0.048 Uiso 1 1 calc R . . . .
C14 C -0.11716(15) 0.28669(15) 0.71085(15) 0.0400(3) Uani 1 1 d . . . . .
C15 C 0.22857(16) 0.28133(15) 0.64547(15) 0.0434(3) Uani 1 1 d . . . . .
C16 C -0.05900(18) -0.29524(15) 0.88164(17) 0.0487(4) Uani 1 1 d . . . . .
H16A H 0.030751 -0.322458 0.930824 0.058 Uiso 1 1 calc R . . . .
H16B H -0.046203 -0.364410 0.810530 0.058 Uiso 1 1 calc R . . . .
C17 C -0.01762(16) 0.28455(15) 0.58531(16) 0.0459(4) Uani 1 1 d . . . . .
H17A H -0.048916 0.238272 0.513294 0.055 Uiso 1 1 calc R . . . .
H17B H -0.023324 0.382367 0.556594 0.055 Uiso 1 1 calc R . . . .
C18 C -0.28302(17) 0.28046(17) 0.95221(16) 0.0480(4) Uani 1 1 d . . . . .
H18 H -0.338713 0.278483 1.033267 0.058 Uiso 1 1 calc R . . . .
C19 C -0.22559(16) 0.41031(15) 0.75763(18) 0.0496(4) Uani 1 1 d . . . . .
H19 H -0.241704 0.496028 0.708081 0.059 Uiso 1 1 calc R . . . .
C20 C -0.22138(16) -0.10904(16) 0.75234(16) 0.0448(3) Uani 1 1 d . . . . .
H20A H -0.211120 -0.174486 0.678508 0.054 Uiso 1 1 calc R . . . .
H20B H -0.239031 -0.012155 0.715112 0.054 Uiso 1 1 calc R . . . .
C21 C -0.35182(18) -0.11460(17) 0.84876(19) 0.0557(4) Uani 1 1 d . . . . .
H21A H -0.365676 -0.044293 0.919029 0.067 Uiso 1 1 calc R . . . .
H21B H -0.442272 -0.089325 0.800636 0.067 Uiso 1 1 calc R . . . .
C22 C -0.30984(17) 0.40743(16) 0.87699(18) 0.0527(4) Uani 1 1 d . . . . .
H22 H -0.384087 0.490124 0.906709 0.063 Uiso 1 1 calc R . . . .
C23 C -0.1930(2) -0.29474(19) 0.9755(2) 0.0613(5) Uani 1 1 d . . . . .
H23A H -0.177645 -0.390324 1.015203 0.074 Uiso 1 1 calc R . . . .
H23B H -0.202127 -0.227942 1.047954 0.074 Uiso 1 1 calc R . . . .
C0AA C 0.4354(2) -0.31451(19) 0.6209(2) 0.0668(5) Uani 1 1 d . . . . .
H0AA H 0.509033 -0.275494 0.576298 0.100 Uiso 1 1 calc GR . . . .
H0AB H 0.414559 -0.381309 0.562625 0.100 Uiso 1 1 calc GR . . . .
H0AC H 0.472804 -0.363673 0.702382 0.100 Uiso 1 1 calc GR . . . .
C1AA C 0.45250(19) 0.2697(2) 0.7430(2) 0.0636(5) Uani 1 1 d . . . . .
H1AA H 0.538718 0.254402 0.680481 0.095 Uiso 1 1 calc GR . . . .
H1AB H 0.483552 0.232078 0.830103 0.095 Uiso 1 1 calc GR . . . .
H1AC H 0.401086 0.371267 0.749153 0.095 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
C1 C2 1.4205(18) . ?
C1 C7 1.4090(19) . ?
C1 C11 1.4853(17) . ?
C2 N4 1.4151(18) . ?
C2 C10 1.3888(19) . ?
O3 C15 1.3390(17) . ?
O3 C1AA 1.4392(19) . ?
N4 C16 1.4591(17) . ?
N4 C20 1.4640(18) . ?
N5 C7 1.4324(16) . ?
N5 C15 1.3675(19) . ?
N5 C17 1.4661(17) . ?
C6 H6 0.9300 . ?
C6 C7 1.3843(19) . ?
C6 C12 1.385(2) . ?
O8 C21 1.4225(18) . ?
O8 C23 1.420(2) . ?
O9 C15 1.2080(18) . ?
C10 H10 0.9300 . ?
C10 C12 1.389(2) . ?
C11 C13 1.398(2) . ?
C11 C14 1.4041(18) . ?
C12 C0AA 1.506(2) . ?
C13 H13 0.9300 . ?
C13 C18 1.387(2) . ?
C14 C17 1.499(2) . ?
C14 C19 1.386(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C23 1.509(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18 0.9300 . ?
C18 C22 1.385(2) . ?
C19 H19 0.9300 . ?
C19 C22 1.380(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.511(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C0AA H0AA 0.9600 . ?
C0AA H0AB 0.9600 . ?
C0AA H0AC 0.9600 . ?
C1AA H1AA 0.9600 . ?
C1AA H1AB 0.9600 . ?
C1AA H1AC 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 C1 C11 125.18(12) . . ?
C7 C1 C2 117.19(12) . . ?
C7 C1 C11 117.55(11) . . ?
N4 C2 C1 119.49(12) . . ?
C10 C2 C1 119.34(13) . . ?
C10 C2 N4 121.16(12) . . ?
C15 O3 C1AA 116.09(12) . . ?
C2 N4 C16 117.77(11) . . ?
C2 N4 C20 116.21(11) . . ?
C16 N4 C20 109.66(11) . . ?
C7 N5 C17 113.16(11) . . ?
C15 N5 C7 125.01(11) . . ?
C15 N5 C17 117.93(12) . . ?
C7 C6 H6 120.0 . . ?
C7 C6 C12 119.97(13) . . ?
C12 C6 H6 120.0 . . ?
C1 C7 N5 116.92(12) . . ?
C6 C7 C1 122.07(12) . . ?
C6 C7 N5 120.98(12) . . ?
C23 O8 C21 109.97(12) . . ?
C2 C10 H10 118.9 . . ?
C12 C10 C2 122.14(13) . . ?
C12 C10 H10 118.9 . . ?
C13 C11 C1 123.91(12) . . ?
C13 C11 C14 118.40(13) . . ?
C14 C11 C1 117.52(12) . . ?
C6 C12 C10 118.86(13) . . ?
C6 C12 C0AA 121.26(14) . . ?
C10 C12 C0AA 119.87(14) . . ?
C11 C13 H13 119.8 . . ?
C18 C13 C11 120.49(13) . . ?
C18 C13 H13 119.8 . . ?
C11 C14 C17 116.46(12) . . ?
C19 C14 C11 120.36(14) . . ?
C19 C14 C17 123.11(13) . . ?
O3 C15 N5 111.82(12) . . ?
O9 C15 O3 124.20(14) . . ?
O9 C15 N5 123.97(14) . . ?
N4 C16 H16A 110.1 . . ?
N4 C16 H16B 110.1 . . ?
N4 C16 C23 108.20(13) . . ?
H16A C16 H16B 108.4 . . ?
C23 C16 H16A 110.1 . . ?
C23 C16 H16B 110.1 . . ?
N5 C17 C14 108.01(11) . . ?
N5 C17 H17A 110.1 . . ?
N5 C17 H17B 110.1 . . ?
C14 C17 H17A 110.1 . . ?
C14 C17 H17B 110.1 . . ?
H17A C17 H17B 108.4 . . ?
C13 C18 H18 119.7 . . ?
C22 C18 C13 120.54(15) . . ?
C22 C18 H18 119.7 . . ?
C14 C19 H19 119.7 . . ?
C22 C19 C14 120.66(14) . . ?
C22 C19 H19 119.7 . . ?
N4 C20 H20A 109.8 . . ?
N4 C20 H20B 109.8 . . ?
N4 C20 C21 109.53(13) . . ?
H20A C20 H20B 108.2 . . ?
C21 C20 H20A 109.8 . . ?
C21 C20 H20B 109.8 . . ?
O8 C21 C20 111.31(13) . . ?
O8 C21 H21A 109.4 . . ?
O8 C21 H21B 109.4 . . ?
C20 C21 H21A 109.4 . . ?
C20 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C18 C22 H22 120.2 . . ?
C19 C22 C18 119.51(14) . . ?
C19 C22 H22 120.2 . . ?
O8 C23 C16 112.25(14) . . ?
O8 C23 H23A 109.2 . . ?
O8 C23 H23B 109.2 . . ?
C16 C23 H23A 109.2 . . ?
C16 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C12 C0AA H0AA 109.5 . . ?
C12 C0AA H0AB 109.5 . . ?
C12 C0AA H0AC 109.5 . . ?
H0AA C0AA H0AB 109.5 . . ?
H0AA C0AA H0AC 109.5 . . ?
H0AB C0AA H0AC 109.5 . . ?
O3 C1AA H1AA 109.5 . . ?
O3 C1AA H1AB 109.5 . . ?
O3 C1AA H1AC 109.5 . . ?
H1AA C1AA H1AB 109.5 . . ?
H1AA C1AA H1AC 109.5 . . ?
H1AB C1AA H1AC 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
C1 C2 N4 C16 -163.43(12) . . . . ?
C1 C2 N4 C20 63.48(16) . . . . ?
C1 C2 C10 C12 -1.8(2) . . . . ?
C1 C11 C13 C18 177.56(12) . . . . ?
C1 C11 C14 C17 -0.02(17) . . . . ?
C1 C11 C14 C19 -177.12(12) . . . . ?
C2 C1 C7 N5 172.00(11) . . . . ?
C2 C1 C7 C6 -6.09(19) . . . . ?
C2 C1 C11 C13 30.43(19) . . . . ?
C2 C1 C11 C14 -154.41(12) . . . . ?
C2 N4 C16 C23 165.58(13) . . . . ?
C2 N4 C20 C21 -164.81(12) . . . . ?
C2 C10 C12 C6 -3.7(2) . . . . ?
C2 C10 C12 C0AA 177.68(15) . . . . ?
N4 C2 C10 C12 179.48(12) . . . . ?
N4 C16 C23 O8 59.25(18) . . . . ?
N4 C20 C21 O8 -57.74(17) . . . . ?
C7 C1 C2 N4 -174.73(11) . . . . ?
C7 C1 C2 C10 6.51(18) . . . . ?
C7 C1 C11 C13 -146.23(13) . . . . ?
C7 C1 C11 C14 28.94(17) . . . . ?
C7 N5 C15 O3 11.4(2) . . . . ?
C7 N5 C15 O9 -169.71(15) . . . . ?
C7 N5 C17 C14 60.81(16) . . . . ?
C7 C6 C12 C10 4.2(2) . . . . ?
C7 C6 C12 C0AA -177.18(15) . . . . ?
C10 C2 N4 C16 15.31(19) . . . . ?
C10 C2 N4 C20 -117.78(14) . . . . ?
C11 C1 C2 N4 8.60(19) . . . . ?
C11 C1 C2 C10 -170.16(12) . . . . ?
C11 C1 C7 N5 -11.08(17) . . . . ?
C11 C1 C7 C6 170.84(12) . . . . ?
C11 C13 C18 C22 -1.2(2) . . . . ?
C11 C14 C17 N5 -42.82(17) . . . . ?
C11 C14 C19 C22 -0.3(2) . . . . ?
C12 C6 C7 C1 0.7(2) . . . . ?
C12 C6 C7 N5 -177.28(12) . . . . ?
C13 C11 C14 C17 175.42(12) . . . . ?
C13 C11 C14 C19 -1.68(19) . . . . ?
C13 C18 C22 C19 -0.8(2) . . . . ?
C14 C11 C13 C18 2.43(19) . . . . ?
C14 C19 C22 C18 1.6(2) . . . . ?
C15 N5 C7 C1 122.75(15) . . . . ?
C15 N5 C7 C6 -59.1(2) . . . . ?
C15 N5 C17 C14 -98.11(14) . . . . ?
C16 N4 C20 C21 58.52(16) . . . . ?
C17 N5 C7 C1 -34.42(17) . . . . ?
C17 N5 C7 C6 143.68(14) . . . . ?
C17 N5 C15 O3 167.60(12) . . . . ?
C17 N5 C15 O9 -13.5(2) . . . . ?
C17 C14 C19 C22 -177.22(14) . . . . ?
C19 C14 C17 N5 134.19(14) . . . . ?
C20 N4 C16 C23 -58.51(16) . . . . ?
C21 O8 C23 C16 -58.52(19) . . . . ?
C23 O8 C21 C20 57.14(19) . . . . ?
C1AA O3 C15 N5 -174.54(14) . . . . ?
C1AA O3 C15 O9 6.6(2) . . . . ?

_olex2_date_sample_data_collection 2019-10-08
_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_anyang_2
_database_code_depnum_ccdc_archive 'CCDC 1958318'
loop_
_audit_author_name
_audit_author_address
'Yang An'
;lanzhou university
China
;
_audit_update_record             
;
2019-10-09 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_audit_creation_date             2019-10-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 F N O2'
_chemical_formula_sum            'C17 H16 F N O2'
_chemical_formula_weight         285.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
F F 0.0727 0.0534 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   17.1703(5)
_cell_length_b                   9.1104(2)
_cell_length_c                   19.1959(6)
_cell_angle_alpha                90
_cell_angle_beta                 115.406(4)
_cell_angle_gamma                90
_cell_volume                     2712.40(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2921
_cell_measurement_temperature    292.59(10)
_cell_measurement_theta_max      69.8640
_cell_measurement_theta_min      7.5500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10281
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        66.591
_diffrn_reflns_theta_max         66.591
_diffrn_reflns_theta_min         4.568
_diffrn_ambient_temperature      292.59(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -9.00   18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega   27.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -120.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega  -83.00  -34.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000   30.0000 49

#__ type_ start__ end____ width___ exp.time_
  4 omega   33.00  112.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -150.0000 79

#__ type_ start__ end____ width___ exp.time_
  5 omega   69.00   97.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000  150.0000 28

#__ type_ start__ end____ width___ exp.time_
  6 omega   87.00  119.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
  7 omega    2.00   53.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000  150.0000 51

#__ type_ start__ end____ width___ exp.time_
  8 omega   68.00  125.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 57

#__ type_ start__ end____ width___ exp.time_
  9 omega   41.00  131.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  -30.0000 90

#__ type_ start__ end____ width___ exp.time_
 10 omega   37.00   66.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   90.0000 29

#__ type_ start__ end____ width___ exp.time_
 11 omega   43.00   70.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 12 omega   38.00   64.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   37.00   68.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -90.0000 31

#__ type_ start__ end____ width___ exp.time_
 14 omega  144.00  174.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -90.0000 30

#__ type_ start__ end____ width___ exp.time_
 15 omega   64.00   90.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   41.00  132.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000   90.0000 91

#__ type_ start__ end____ width___ exp.time_
 17 omega   91.00  174.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -180.0000 83

#__ type_ start__ end____ width___ exp.time_
 18 omega   85.00  111.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   44.00  113.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 69

#__ type_ start__ end____ width___ exp.time_
 20 omega   43.00   72.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -150.0000 29

#__ type_ start__ end____ width___ exp.time_
 21 omega   69.00  104.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  150.0000 35
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0164139000
_diffrn_orient_matrix_UB_12      0.0134090000
_diffrn_orient_matrix_UB_13      0.0725922000
_diffrn_orient_matrix_UB_21      0.0798651000
_diffrn_orient_matrix_UB_22      -0.0957929000
_diffrn_orient_matrix_UB_23      0.0451189000
_diffrn_orient_matrix_UB_31      0.0567133000
_diffrn_orient_matrix_UB_32      0.1387517000
_diffrn_orient_matrix_UB_33      0.0241632000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3489
_reflns_number_total             4680
_reflns_odcompleteness_completeness 97.70
_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, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         4680
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0433
_refine_ls_restrained_S_all      1.050
_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)+(0.0480P)²+0.3809P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1189
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C17(H17A,H17B), C23(H23A,H23B), C26(H26A,H26B), C28(H28A,H28B),
 C29(H29A,H29B), C33(H33A,H33B), C36(H36A,H36B), C37(H37A,H37B), C41(H41A,H41B)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C22(H22), C24(H24), C30(H30), C31(H31), C32(H32), C34(H34),
 C35(H35), C38(H38), C39(H39), C40(H40), C0AA(H0AA)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.10160(7) 0.92757(15) 0.22093(7) 0.0613(3) Uani 1 1 d . . . . .
F2 F -0.09586(7) 0.66102(16) 0.28756(7) 0.0647(4) Uani 1 1 d . . . . .
N3 N -0.31421(8) 0.89219(16) 0.10492(8) 0.0350(3) Uani 1 1 d . . . . .
N4 N 0.31941(8) 0.68786(17) 0.39510(8) 0.0361(3) Uani 1 1 d . . . . .
O5 O -0.08354(8) 1.23841(15) 0.14541(8) 0.0496(3) Uani 1 1 d . . . . .
O6 O -0.39237(8) 0.65993(16) 0.15144(8) 0.0538(4) Uani 1 1 d . . . . .
C7 C 0.13771(10) 0.6423(2) 0.37487(9) 0.0357(4) Uani 1 1 d . . . . .
O8 O 0.08789(9) 0.34819(16) 0.36256(9) 0.0544(4) Uani 1 1 d . . . . .
C9 C 0.28129(10) 0.7386(2) 0.31458(10) 0.0383(4) Uani 1 1 d . . . . .
H9A H 0.219120 0.727640 0.292604 0.046 Uiso 1 1 calc R . . . .
H9B H 0.302712 0.678997 0.284672 0.046 Uiso 1 1 calc R . . . .
O10 O 0.39481(9) 0.91788(17) 0.34357(9) 0.0596(4) Uani 1 1 d . . . . .
C11 C 0.17356(12) 0.3800(2) 0.38424(11) 0.0453(4) Uani 1 1 d . . . . .
C12 C -0.19695(10) 1.05972(19) 0.11793(9) 0.0344(4) Uani 1 1 d . . . . .
C13 C -0.04559(10) 0.9850(2) 0.17099(9) 0.0380(4) Uani 1 1 d . . . . .
C14 C -0.01211(11) 0.7031(2) 0.32726(10) 0.0448(4) Uani 1 1 d . . . . .
C15 C 0.01809(11) 0.8843(2) 0.18068(10) 0.0430(4) Uani 1 1 d . . . . .
C16 C -0.13196(10) 0.9433(2) 0.13065(9) 0.0346(4) Uani 1 1 d . . . . .
C17 C -0.28072(10) 0.8435(2) 0.18545(9) 0.0373(4) Uani 1 1 d . . . . .
H17A H -0.306089 0.902191 0.212564 0.045 Uiso 1 1 calc R . . . .
H17B H -0.218733 0.857297 0.210596 0.045 Uiso 1 1 calc R . . . .
C18 C 0.20191(10) 0.5248(2) 0.38607(9) 0.0360(4) Uani 1 1 d . . . . .
C19 C -0.34219(11) 1.1546(2) 0.07483(11) 0.0460(4) Uani 1 1 d . . . . .
H19 H -0.400879 1.138639 0.058727 0.055 Uiso 1 1 calc R . . . .
C20 C 0.29061(10) 0.5466(2) 0.40378(9) 0.0364(4) Uani 1 1 d . . . . .
C21 C -0.28593(10) 1.03626(19) 0.09803(9) 0.0349(4) Uani 1 1 d . . . . .
C22 C -0.15025(11) 0.8019(2) 0.10034(10) 0.0414(4) Uani 1 1 d . . . . .
H22 H -0.207208 0.773234 0.071848 0.050 Uiso 1 1 calc R . . . .
C23 C 0.41292(10) 0.7094(2) 0.42855(10) 0.0444(4) Uani 1 1 d . . . . .
H23A H 0.437756 0.648413 0.401853 0.053 Uiso 1 1 calc R . . . .
H23B H 0.438360 0.681242 0.482490 0.053 Uiso 1 1 calc R . . . .
C24 C 0.00183(12) 0.7442(2) 0.15294(11) 0.0484(5) Uani 1 1 d . . . . .
H24 H 0.046387 0.678660 0.160867 0.058 Uiso 1 1 calc R . . . .
C25 C -0.16949(11) 1.2055(2) 0.12206(10) 0.0414(4) Uani 1 1 d . . . . .
C26 C -0.30168(11) 0.6842(2) 0.18913(11) 0.0454(4) Uani 1 1 d . . . . .
H26A H -0.273408 0.625122 0.164684 0.055 Uiso 1 1 calc R . . . .
H26B H -0.279986 0.653908 0.242621 0.055 Uiso 1 1 calc R . . . .
C27 C 0.05075(10) 0.6015(2) 0.33587(9) 0.0390(4) Uani 1 1 d . . . . .
C28 C -0.40698(10) 0.8652(2) 0.06607(10) 0.0434(4) Uani 1 1 d . . . . .
H28A H -0.428702 0.891631 0.012038 0.052 Uiso 1 1 calc R . . . .
H28B H -0.436353 0.925061 0.089205 0.052 Uiso 1 1 calc R . . . .
C29 C 0.03166(12) 0.4481(2) 0.30585(11) 0.0484(5) Uani 1 1 d . . . . .
H29A H -0.027834 0.424198 0.293679 0.058 Uiso 1 1 calc R . . . .
H29B H 0.039664 0.439680 0.258967 0.058 Uiso 1 1 calc R . . . .
C30 C 0.15727(11) 0.7847(2) 0.40439(10) 0.0415(4) Uani 1 1 d . . . . .
H30 H 0.214486 0.813615 0.431061 0.050 Uiso 1 1 calc R . . . .
C31 C 0.00550(12) 0.8431(2) 0.35516(11) 0.0506(5) Uani 1 1 d . . . . .
H31 H -0.038507 0.909028 0.348397 0.061 Uiso 1 1 calc R . . . .
C32 C -0.22620(13) 1.3228(2) 0.10029(13) 0.0537(5) Uani 1 1 d . . . . .
H32 H -0.206102 1.418293 0.102593 0.064 Uiso 1 1 calc R . . . .
C33 C -0.02758(11) 1.1376(2) 0.20210(11) 0.0462(4) Uani 1 1 d . . . . .
H33A H -0.036723 1.144237 0.248484 0.055 Uiso 1 1 calc R . . . .
H33B H 0.032042 1.162599 0.215377 0.055 Uiso 1 1 calc R . . . .
C34 C -0.08389(12) 0.7034(2) 0.11241(11) 0.0480(5) Uani 1 1 d . . . . .
H34 H -0.097128 0.608510 0.093006 0.058 Uiso 1 1 calc R . . . .
C35 C 0.34601(12) 0.4271(2) 0.42765(12) 0.0509(5) Uani 1 1 d . . . . .
H35 H 0.404613 0.441503 0.442495 0.061 Uiso 1 1 calc R . . . .
C36 C -0.42438(12) 0.7049(3) 0.07339(12) 0.0556(5) Uani 1 1 d . . . . .
H36A H -0.486030 0.687373 0.047972 0.067 Uiso 1 1 calc R . . . .
H36B H -0.397563 0.646228 0.047485 0.067 Uiso 1 1 calc R . . . .
C37 C 0.30378(12) 0.8969(2) 0.31053(12) 0.0501(5) Uani 1 1 d . . . . .
H37A H 0.278932 0.928390 0.257094 0.060 Uiso 1 1 calc R . . . .
H37B H 0.279235 0.956930 0.337844 0.060 Uiso 1 1 calc R . . . .
C38 C 0.09148(13) 0.8831(2) 0.39396(11) 0.0492(5) Uani 1 1 d . . . . .
H38 H 0.105315 0.977890 0.413383 0.059 Uiso 1 1 calc R . . . .
C39 C 0.22984(15) 0.2620(2) 0.40668(14) 0.0610(6) Uani 1 1 d . . . . .
H39 H 0.209474 0.167152 0.406038 0.073 Uiso 1 1 calc R . . . .
C40 C 0.31610(15) 0.2873(2) 0.42985(15) 0.0643(6) Uani 1 1 d . . . . .
H40 H 0.354844 0.209615 0.447226 0.077 Uiso 1 1 calc R . . . .
C41 C 0.43192(13) 0.8686(3) 0.42111(13) 0.0598(6) Uani 1 1 d . . . . .
H41A H 0.409987 0.927909 0.450726 0.072 Uiso 1 1 calc R . . . .
H41B H 0.493883 0.882403 0.442828 0.072 Uiso 1 1 calc R . . . .
C0AA C -0.31271(13) 1.2955(2) 0.07521(13) 0.0557(5) Uani 1 1 d . . . . .
H0AA H -0.351786 1.372834 0.058314 0.067 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 1.363(2) . ?
F2 C14 1.362(2) . ?
N3 C17 1.468(2) . ?
N3 C21 1.425(2) . ?
N3 C28 1.4611(19) . ?
N4 C9 1.471(2) . ?
N4 C20 1.414(2) . ?
N4 C23 1.4643(19) . ?
O5 C25 1.379(2) . ?
O5 C33 1.433(2) . ?
O6 C26 1.425(2) . ?
O6 C36 1.417(2) . ?
C7 C18 1.484(2) . ?
C7 C27 1.403(2) . ?
C7 C30 1.398(3) . ?
O8 C11 1.377(2) . ?
O8 C29 1.430(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C37 1.504(3) . ?
O10 C37 1.425(2) . ?
O10 C41 1.417(3) . ?
C11 C18 1.402(3) . ?
C11 C39 1.385(3) . ?
C12 C16 1.482(2) . ?
C12 C21 1.423(2) . ?
C12 C25 1.400(3) . ?
C13 C15 1.378(3) . ?
C13 C16 1.399(2) . ?
C13 C33 1.493(3) . ?
C14 C27 1.377(3) . ?
C14 C31 1.366(3) . ?
C15 C24 1.365(3) . ?
C16 C22 1.393(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C26 1.504(3) . ?
C18 C20 1.425(2) . ?
C19 H19 0.9300 . ?
C19 C21 1.388(2) . ?
C19 C0AA 1.378(3) . ?
C20 C35 1.388(3) . ?
C22 H22 0.9300 . ?
C22 C34 1.390(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C41 1.506(3) . ?
C24 H24 0.9300 . ?
C24 C34 1.388(3) . ?
C25 C32 1.384(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C29 1.493(3) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C36 1.510(3) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30 0.9300 . ?
C30 C38 1.388(3) . ?
C31 H31 0.9300 . ?
C31 C38 1.387(3) . ?
C32 H32 0.9300 . ?
C32 C0AA 1.374(3) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C35 C40 1.380(3) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
C39 C40 1.371(3) . ?
C40 H40 0.9300 . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C0AA H0AA 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 N3 C17 112.40(13) . . ?
C21 N3 C28 116.60(14) . . ?
C28 N3 C17 109.60(13) . . ?
C20 N4 C9 112.91(13) . . ?
C20 N4 C23 116.33(14) . . ?
C23 N4 C9 109.18(13) . . ?
C25 O5 C33 112.52(14) . . ?
C36 O6 C26 109.61(14) . . ?
C27 C7 C18 116.12(16) . . ?
C30 C7 C18 125.18(15) . . ?
C30 C7 C27 118.55(16) . . ?
C11 O8 C29 112.40(14) . . ?
N4 C9 H9A 109.6 . . ?
N4 C9 H9B 109.6 . . ?
N4 C9 C37 110.32(15) . . ?
H9A C9 H9B 108.1 . . ?
C37 C9 H9A 109.6 . . ?
C37 C9 H9B 109.6 . . ?
C41 O10 C37 109.75(14) . . ?
O8 C11 C18 121.34(17) . . ?
O8 C11 C39 116.31(18) . . ?
C39 C11 C18 122.31(18) . . ?
C21 C12 C16 125.64(16) . . ?
C25 C12 C16 117.26(15) . . ?
C25 C12 C21 117.02(16) . . ?
C15 C13 C16 119.04(18) . . ?
C15 C13 C33 123.40(16) . . ?
C16 C13 C33 117.56(16) . . ?
F2 C14 C27 117.59(19) . . ?
F2 C14 C31 119.01(17) . . ?
C31 C14 C27 123.39(18) . . ?
F1 C15 C13 117.69(18) . . ?
F1 C15 C24 118.77(17) . . ?
C24 C15 C13 123.54(17) . . ?
C13 C16 C12 116.20(16) . . ?
C22 C16 C12 125.05(15) . . ?
C22 C16 C13 118.52(16) . . ?
N3 C17 H17A 109.6 . . ?
N3 C17 H17B 109.6 . . ?
N3 C17 C26 110.34(14) . . ?
H17A C17 H17B 108.1 . . ?
C26 C17 H17A 109.6 . . ?
C26 C17 H17B 109.6 . . ?
C11 C18 C7 116.53(15) . . ?
C11 C18 C20 117.45(16) . . ?
C20 C18 C7 125.86(16) . . ?
C21 C19 H19 119.4 . . ?
C0AA C19 H19 119.4 . . ?
C0AA C19 C21 121.22(17) . . ?
N4 C20 C18 119.36(15) . . ?
C35 C20 N4 121.87(15) . . ?
C35 C20 C18 118.75(17) . . ?
C12 C21 N3 118.87(14) . . ?
C19 C21 N3 121.83(15) . . ?
C19 C21 C12 119.27(16) . . ?
C16 C22 H22 119.8 . . ?
C34 C22 C16 120.40(17) . . ?
C34 C22 H22 119.8 . . ?
N4 C23 H23A 109.8 . . ?
N4 C23 H23B 109.8 . . ?
N4 C23 C41 109.21(16) . . ?
H23A C23 H23B 108.3 . . ?
C41 C23 H23A 109.8 . . ?
C41 C23 H23B 109.8 . . ?
C15 C24 H24 121.3 . . ?
C15 C24 C34 117.34(17) . . ?
C34 C24 H24 121.3 . . ?
O5 C25 C12 120.80(16) . . ?
O5 C25 C32 116.52(17) . . ?
C32 C25 C12 122.62(17) . . ?
O6 C26 C17 110.92(15) . . ?
O6 C26 H26A 109.5 . . ?
O6 C26 H26B 109.5 . . ?
C17 C26 H26A 109.5 . . ?
C17 C26 H26B 109.5 . . ?
H26A C26 H26B 108.0 . . ?
C7 C27 C29 117.46(16) . . ?
C14 C27 C7 119.05(18) . . ?
C14 C27 C29 123.48(17) . . ?
N3 C28 H28A 109.8 . . ?
N3 C28 H28B 109.8 . . ?
N3 C28 C36 109.34(15) . . ?
H28A C28 H28B 108.3 . . ?
C36 C28 H28A 109.8 . . ?
C36 C28 H28B 109.8 . . ?
O8 C29 C27 109.71(15) . . ?
O8 C29 H29A 109.7 . . ?
O8 C29 H29B 109.7 . . ?
C27 C29 H29A 109.7 . . ?
C27 C29 H29B 109.7 . . ?
H29A C29 H29B 108.2 . . ?
C7 C30 H30 119.9 . . ?
C38 C30 C7 120.13(17) . . ?
C38 C30 H30 119.9 . . ?
C14 C31 H31 121.2 . . ?
C14 C31 C38 117.51(18) . . ?
C38 C31 H31 121.2 . . ?
C25 C32 H32 120.6 . . ?
C0AA C32 C25 118.75(18) . . ?
C0AA C32 H32 120.6 . . ?
O5 C33 C13 109.68(15) . . ?
O5 C33 H33A 109.7 . . ?
O5 C33 H33B 109.7 . . ?
C13 C33 H33A 109.7 . . ?
C13 C33 H33B 109.7 . . ?
H33A C33 H33B 108.2 . . ?
C22 C34 H34 119.4 . . ?
C24 C34 C22 121.13(19) . . ?
C24 C34 H34 119.4 . . ?
C20 C35 H35 119.3 . . ?
C40 C35 C20 121.48(18) . . ?
C40 C35 H35 119.3 . . ?
O6 C36 C28 112.05(17) . . ?
O6 C36 H36A 109.2 . . ?
O6 C36 H36B 109.2 . . ?
C28 C36 H36A 109.2 . . ?
C28 C36 H36B 109.2 . . ?
H36A C36 H36B 107.9 . . ?
C9 C37 H37A 109.4 . . ?
C9 C37 H37B 109.4 . . ?
O10 C37 C9 111.25(16) . . ?
O10 C37 H37A 109.4 . . ?
O10 C37 H37B 109.4 . . ?
H37A C37 H37B 108.0 . . ?
C30 C38 H38 119.3 . . ?
C31 C38 C30 121.4(2) . . ?
C31 C38 H38 119.3 . . ?
C11 C39 H39 120.6 . . ?
C40 C39 C11 118.85(19) . . ?
C40 C39 H39 120.6 . . ?
C35 C40 H40 119.7 . . ?
C39 C40 C35 120.66(19) . . ?
C39 C40 H40 119.7 . . ?
O10 C41 C23 112.73(17) . . ?
O10 C41 H41A 109.0 . . ?
O10 C41 H41B 109.0 . . ?
C23 C41 H41A 109.0 . . ?
C23 C41 H41B 109.0 . . ?
H41A C41 H41B 107.8 . . ?
C19 C0AA H0AA 119.7 . . ?
C32 C0AA C19 120.65(18) . . ?
C32 C0AA H0AA 119.7 . . ?

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
F1 C15 C24 C34 179.80(15) . . . . ?
F2 C14 C27 C7 178.49(14) . . . . ?
F2 C14 C27 C29 -1.6(3) . . . . ?
F2 C14 C31 C38 -178.72(16) . . . . ?
N3 C17 C26 O6 -58.25(19) . . . . ?
N3 C28 C36 O6 58.4(2) . . . . ?
N4 C9 C37 O10 58.2(2) . . . . ?
N4 C20 C35 C40 -174.56(19) . . . . ?
N4 C23 C41 O10 -58.2(2) . . . . ?
O5 C25 C32 C0AA 178.82(18) . . . . ?
C7 C18 C20 N4 -14.1(2) . . . . ?
C7 C18 C20 C35 167.19(16) . . . . ?
C7 C27 C29 O8 43.2(2) . . . . ?
C7 C30 C38 C31 0.7(3) . . . . ?
O8 C11 C18 C7 8.8(3) . . . . ?
O8 C11 C18 C20 -175.55(15) . . . . ?
O8 C11 C39 C40 -179.15(19) . . . . ?
C9 N4 C20 C18 -64.44(19) . . . . ?
C9 N4 C20 C35 114.22(18) . . . . ?
C9 N4 C23 C41 56.42(19) . . . . ?
C11 O8 C29 C27 -57.2(2) . . . . ?
C11 C18 C20 N4 170.65(15) . . . . ?
C11 C18 C20 C35 -8.0(2) . . . . ?
C11 C39 C40 C35 -2.8(4) . . . . ?
C12 C16 C22 C34 176.49(16) . . . . ?
C12 C25 C32 C0AA 1.5(3) . . . . ?
C13 C15 C24 C34 0.5(3) . . . . ?
C13 C16 C22 C34 2.2(3) . . . . ?
C14 C27 C29 O8 -136.75(17) . . . . ?
C14 C31 C38 C30 -0.2(3) . . . . ?
C15 C13 C16 C12 -176.13(15) . . . . ?
C15 C13 C16 C22 -1.3(2) . . . . ?
C15 C13 C33 O5 137.41(16) . . . . ?
C15 C24 C34 C22 0.4(3) . . . . ?
C16 C12 C21 N3 13.1(2) . . . . ?
C16 C12 C21 C19 -168.87(16) . . . . ?
C16 C12 C25 O5 -7.0(2) . . . . ?
C16 C12 C25 C32 170.27(17) . . . . ?
C16 C13 C15 F1 -179.32(14) . . . . ?
C16 C13 C15 C24 0.0(3) . . . . ?
C16 C13 C33 O5 -43.2(2) . . . . ?
C16 C22 C34 C24 -1.7(3) . . . . ?
C17 N3 C21 C12 67.37(19) . . . . ?
C17 N3 C21 C19 -110.58(18) . . . . ?
C17 N3 C28 C36 -55.95(19) . . . . ?
C18 C7 C27 C14 176.50(15) . . . . ?
C18 C7 C27 C29 -3.4(2) . . . . ?
C18 C7 C30 C38 -176.27(16) . . . . ?
C18 C11 C39 C40 -1.5(3) . . . . ?
C18 C20 C35 C40 4.1(3) . . . . ?
C20 N4 C9 C37 171.58(14) . . . . ?
C20 N4 C23 C41 -174.37(15) . . . . ?
C20 C35 C40 C39 1.5(4) . . . . ?
C21 N3 C17 C26 -171.96(13) . . . . ?
C21 N3 C28 C36 174.95(15) . . . . ?
C21 C12 C16 C13 -161.87(15) . . . . ?
C21 C12 C16 C22 23.7(3) . . . . ?
C21 C12 C25 O5 176.10(15) . . . . ?
C21 C12 C25 C32 -6.7(3) . . . . ?
C21 C19 C0AA C32 -1.4(3) . . . . ?
C23 N4 C9 C37 -57.36(18) . . . . ?
C23 N4 C20 C18 168.18(14) . . . . ?
C23 N4 C20 C35 -13.2(2) . . . . ?
C25 O5 C33 C13 57.23(19) . . . . ?
C25 C12 C16 C13 21.5(2) . . . . ?
C25 C12 C16 C22 -152.94(17) . . . . ?
C25 C12 C21 N3 -170.23(15) . . . . ?
C25 C12 C21 C19 7.8(2) . . . . ?
C25 C32 C0AA C19 2.7(3) . . . . ?
C26 O6 C36 C28 -59.3(2) . . . . ?
C27 C7 C18 C11 -23.2(2) . . . . ?
C27 C7 C18 C20 161.50(15) . . . . ?
C27 C7 C30 C38 -0.9(3) . . . . ?
C27 C14 C31 C38 0.1(3) . . . . ?
C28 N3 C17 C26 56.68(18) . . . . ?
C28 N3 C21 C12 -164.89(14) . . . . ?
C28 N3 C21 C19 17.2(2) . . . . ?
C29 O8 C11 C18 32.6(2) . . . . ?
C29 O8 C11 C39 -149.68(19) . . . . ?
C30 C7 C18 C11 152.23(17) . . . . ?
C30 C7 C18 C20 -23.0(3) . . . . ?
C30 C7 C27 C14 0.7(2) . . . . ?
C30 C7 C27 C29 -179.20(15) . . . . ?
C31 C14 C27 C7 -0.3(3) . . . . ?
C31 C14 C27 C29 179.61(17) . . . . ?
C33 O5 C25 C12 -33.6(2) . . . . ?
C33 O5 C25 C32 149.03(18) . . . . ?
C33 C13 C15 F1 0.1(3) . . . . ?
C33 C13 C15 C24 179.35(17) . . . . ?
C33 C13 C16 C12 4.4(2) . . . . ?
C33 C13 C16 C22 179.27(16) . . . . ?
C36 O6 C26 C17 58.8(2) . . . . ?
C37 O10 C41 C23 58.1(2) . . . . ?
C39 C11 C18 C7 -168.78(19) . . . . ?
C39 C11 C18 C20 6.9(3) . . . . ?
C41 O10 C37 C9 -57.5(2) . . . . ?
C0AA C19 C21 N3 173.95(18) . . . . ?
C0AA C19 C21 C12 -4.0(3) . . . . ?

_olex2_date_sample_data_collection 2019-10-08
_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_anxiang_0625
_database_code_depnum_ccdc_archive 'CCDC 1958316'
loop_
_audit_author_name
_audit_author_address
'Yang An'
;lanzhou university
China
;
_audit_update_record             
;
2019-10-09 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_audit_creation_date             2019-07-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C17 H16 N2 O)'
_chemical_formula_sum            'C34 H32 N4 O2'
_chemical_formula_weight         528.63
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.9106(5)
_cell_length_b                   6.1532(3)
_cell_length_c                   37.0164(17)
_cell_angle_alpha                90
_cell_angle_beta                 97.119(4)
_cell_angle_gamma                90
_cell_volume                     2692.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3371
_cell_measurement_temperature    173.20(10)
_cell_measurement_theta_max      69.9510
_cell_measurement_theta_min      8.6220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            9014
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.569
_diffrn_reflns_theta_max         66.569
_diffrn_reflns_theta_min         3.784
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.20(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     38.00 111.00   1.00    3.00    --  108.00 -50.00  90.00   73
  2  ω     97.00 168.00   1.00    3.00    --  108.00  38.00 -30.00   71
  3  ω    151.00 176.00   1.00    3.00    --  108.00  61.00  18.00   25
  4  ω    102.00 137.00   1.00    3.00    --  108.00 111.00-120.00   35
  5  ω     93.00 168.00   1.00    3.00    --  108.00  63.00   0.00   75
  6  ω     39.00 134.00   1.00    3.00    --  108.00 -77.00-120.00   95
  7  ω     36.00 129.00   1.00    3.00    --  108.00  12.00-180.00   93
  8  ω     28.00 125.00   1.00    2.00    --   54.00  38.00   0.00   97
  9  ω     34.00  61.00   1.00    1.00    --    0.00  57.00-150.00   27
 10  ω    -14.00  11.00   1.00    1.00    --    0.00  57.00-150.00   25
 11  ω    -18.00  78.00   1.00    2.00    --   54.00 -38.00-180.00   96
 12  ω     28.00  54.00   1.00    2.00    --   54.00 -77.00-180.00   26
 13  ω     26.00  75.00   1.00    2.00    --   54.00-125.00-180.00   49
 14  ω    -20.00  13.00   1.00    1.00    --    0.00 -57.00 -90.00   33
 15  ω    -62.00 -35.00   1.00    1.00    --    0.00 -57.00 -90.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1064094000
_diffrn_orient_matrix_UB_12      0.1115848000
_diffrn_orient_matrix_UB_13      0.0110302000
_diffrn_orient_matrix_UB_21      -0.0748393000
_diffrn_orient_matrix_UB_22      -0.1403276000
_diffrn_orient_matrix_UB_23      -0.0277644000
_diffrn_orient_matrix_UB_31      -0.0076704000
_diffrn_orient_matrix_UB_32      -0.1748760000
_diffrn_orient_matrix_UB_33      0.0294334000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3983
_reflns_number_total             4756
_reflns_odcompleteness_completeness 99.81
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4756
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.046
_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)+(0.0528P)²+0.4209P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_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, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C16(H16A,H16B), C32(H32A,H32B), C30(H30A,
 H30B), C34(H34A,H34B), C36(H36A,H36B), C40(H40A,H40B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C24(H24), C26(H26), C28(H28), C29(H29),
 C31(H31), C23(H23), C25(H25), C27(H27), C33(H33), C35(H35), C37(H37), C38(H38),
  C39(H39)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.35202(9) 0.44810(18) 0.10054(3) 0.0358(3) Uani 1 1 d . . . . .
N2 N 0.49894(11) 0.8949(2) 0.29238(3) 0.0319(3) Uani 1 1 d . . . . .
C3 C 0.45838(11) 0.7177(2) 0.27147(4) 0.0265(3) Uani 1 1 d . . . . .
N4 N 0.42097(9) 0.49540(18) 0.17660(3) 0.0222(3) Uani 1 1 d . . . . .
C6 C 0.47742(11) 0.6879(2) 0.23449(4) 0.0211(3) Uani 1 1 d . . . . .
C7 C 0.59406(11) 1.0180(2) 0.24202(4) 0.0246(3) Uani 1 1 d . . . . .
C8 C 0.55706(11) 0.8357(2) 0.22030(4) 0.0214(3) Uani 1 1 d . . . . .
C11 C 0.60592(11) 0.8069(2) 0.18762(4) 0.0250(3) Uani 1 1 d . . . . .
H11 H 0.586105 0.686206 0.173086 0.030 Uiso 1 1 calc R . . . .
C12 C 0.55845(12) 1.0370(3) 0.27747(4) 0.0308(3) Uani 1 1 d . . . . .
H12 H 0.579902 1.161536 0.290798 0.037 Uiso 1 1 calc R . . . .
C13 C 0.39722(13) 0.2819(2) 0.16019(4) 0.0294(3) Uani 1 1 d . . . . .
H13A H 0.318725 0.243328 0.161244 0.035 Uiso 1 1 calc R . . . .
H13B H 0.444658 0.172863 0.173443 0.035 Uiso 1 1 calc R . . . .
C14 C 0.66922(12) 1.1697(2) 0.23012(4) 0.0312(3) Uani 1 1 d . . . . .
H14 H 0.689745 1.291705 0.244242 0.037 Uiso 1 1 calc R . . . .
C15 C 0.34794(12) 0.6574(2) 0.15609(4) 0.0258(3) Uani 1 1 d . . . . .
H15A H 0.363828 0.800413 0.166513 0.031 Uiso 1 1 calc R . . . .
H15B H 0.269220 0.623583 0.157780 0.031 Uiso 1 1 calc R . . . .
C16 C 0.36844(14) 0.6579(2) 0.11660(4) 0.0321(3) Uani 1 1 d . . . . .
H16A H 0.317205 0.760264 0.103178 0.039 Uiso 1 1 calc R . . . .
H16B H 0.445202 0.705721 0.114898 0.039 Uiso 1 1 calc R . . . .
C17 C 0.41902(11) 0.5126(2) 0.21497(4) 0.0225(3) Uani 1 1 d . . . . .
C24 C 0.35880(12) 0.3661(3) 0.23326(4) 0.0299(3) Uani 1 1 d . . . . .
H24 H 0.323590 0.249148 0.220581 0.036 Uiso 1 1 calc R . . . .
C26 C 0.71279(13) 1.1403(3) 0.19790(4) 0.0343(4) Uani 1 1 d . . . . .
H26 H 0.761983 1.242133 0.189971 0.041 Uiso 1 1 calc R . . . .
C28 C 0.39642(13) 0.5645(3) 0.28908(4) 0.0334(4) Uani 1 1 d . . . . .
H28 H 0.387484 0.582850 0.313498 0.040 Uiso 1 1 calc R . . . .
C29 C 0.68221(12) 0.9546(3) 0.17707(4) 0.0313(3) Uani 1 1 d . . . . .
H29 H 0.714078 0.930738 0.155710 0.038 Uiso 1 1 calc R . . . .
C31 C 0.34937(13) 0.3890(3) 0.27040(5) 0.0353(4) Uani 1 1 d . . . . .
H31 H 0.311075 0.284663 0.282329 0.042 Uiso 1 1 calc R . . . .
C32 C 0.42083(14) 0.2897(3) 0.12103(4) 0.0348(4) Uani 1 1 d . . . . .
H32A H 0.499966 0.324427 0.120311 0.042 Uiso 1 1 calc R . . . .
H32B H 0.406435 0.147833 0.110010 0.042 Uiso 1 1 calc R . . . .
N5 N 0.78379(10) 0.1274(2) 0.02222(3) 0.0278(3) Uani 1 1 d . . . . .
O9 O 0.62474(11) 0.0694(2) -0.04108(3) 0.0496(3) Uani 1 1 d . . . . .
N10 N 1.07816(11) -0.0987(2) 0.12093(3) 0.0367(3) Uani 1 1 d . . . . .
C18 C 0.90501(12) -0.3074(3) 0.11297(4) 0.0292(3) Uani 1 1 d . . . . .
C19 C 0.85169(12) -0.1624(2) 0.08655(4) 0.0254(3) Uani 1 1 d . . . . .
C20 C 0.91947(12) 0.0163(2) 0.07485(4) 0.0269(3) Uani 1 1 d . . . . .
C21 C 1.02926(12) 0.0458(3) 0.09455(4) 0.0320(3) Uani 1 1 d . . . . .
C22 C 0.88536(12) 0.1665(2) 0.04604(4) 0.0280(3) Uani 1 1 d . . . . .
C23 C 0.68059(13) -0.3764(3) 0.08699(4) 0.0349(4) Uani 1 1 d . . . . .
H23 H 0.604182 -0.396810 0.078978 0.042 Uiso 1 1 calc R . . . .
C25 C 1.01889(13) -0.2656(3) 0.12850(4) 0.0353(4) Uani 1 1 d . . . . .
H25 H 1.052963 -0.365410 0.145265 0.042 Uiso 1 1 calc R . . . .
C27 C 0.73723(14) -0.5267(3) 0.11116(4) 0.0375(4) Uani 1 1 d . . . . .
H27 H 0.700179 -0.650101 0.118066 0.045 Uiso 1 1 calc R . . . .
C30 C 0.79460(13) -0.0528(3) -0.00328(4) 0.0320(3) Uani 1 1 d . . . . .
H30A H 0.827823 -0.177916 0.009933 0.038 Uiso 1 1 calc R . . . .
H30B H 0.844091 -0.009933 -0.020964 0.038 Uiso 1 1 calc R . . . .
C33 C 0.73563(12) -0.1992(3) 0.07485(4) 0.0294(3) Uani 1 1 d . . . . .
H33 H 0.695983 -0.102357 0.058720 0.035 Uiso 1 1 calc R . . . .
C34 C 0.67981(15) -0.1120(3) -0.02261(4) 0.0400(4) Uani 1 1 d . . . . .
H34A H 0.688262 -0.226559 -0.040073 0.048 Uiso 1 1 calc R . . . .
H34B H 0.633037 -0.167468 -0.005017 0.048 Uiso 1 1 calc R . . . .
C35 C 0.84785(13) -0.4893(3) 0.12445(4) 0.0339(4) Uani 1 1 d . . . . .
H35 H 0.885463 -0.585100 0.141215 0.041 Uiso 1 1 calc R . . . .
C36 C 0.73209(14) 0.3125(3) 0.00188(5) 0.0378(4) Uani 1 1 d . . . . .
H36A H 0.779423 0.358950 -0.016197 0.045 Uiso 1 1 calc R . . . .
H36B H 0.724274 0.433110 0.018263 0.045 Uiso 1 1 calc R . . . .
C37 C 0.95171(14) 0.3456(3) 0.04123(5) 0.0357(4) Uani 1 1 d . . . . .
H37 H 0.927301 0.445952 0.023170 0.043 Uiso 1 1 calc R . . . .
C38 C 1.09459(13) 0.2289(3) 0.08850(5) 0.0395(4) Uani 1 1 d . . . . .
H38 H 1.165212 0.247874 0.101936 0.047 Uiso 1 1 calc R . . . .
C39 C 1.05498(14) 0.3792(3) 0.06300(5) 0.0408(4) Uani 1 1 d . . . . .
H39 H 1.096674 0.504354 0.060054 0.049 Uiso 1 1 calc R . . . .
C40 C 0.61717(16) 0.2447(3) -0.01653(5) 0.0482(5) Uani 1 1 d . . . . .
H40A H 0.570078 0.201743 0.001832 0.058 Uiso 1 1 calc R . . . .
H40B H 0.581297 0.367587 -0.029706 0.058 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C16 1.4244(18) . ?
O1 C32 1.4294(19) . ?
N2 C3 1.389(2) . ?
N2 C12 1.292(2) . ?
C3 C6 1.4268(19) . ?
C3 C28 1.406(2) . ?
N4 C13 1.4604(17) . ?
N4 C15 1.4706(17) . ?
N4 C17 1.4275(18) . ?
C6 C8 1.4585(19) . ?
C6 C17 1.4298(19) . ?
C7 C8 1.4178(19) . ?
C7 C12 1.433(2) . ?
C7 C14 1.402(2) . ?
C8 C11 1.4171(19) . ?
C11 H11 0.9300 . ?
C11 C29 1.376(2) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C32 1.511(2) . ?
C14 H14 0.9300 . ?
C14 C26 1.370(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.512(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C24 1.381(2) . ?
C24 H24 0.9300 . ?
C24 C31 1.400(2) . ?
C26 H26 0.9300 . ?
C26 C29 1.401(2) . ?
C28 H28 0.9300 . ?
C28 C31 1.365(2) . ?
C29 H29 0.9300 . ?
C31 H31 0.9300 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
N5 C22 1.4263(19) . ?
N5 C30 1.4720(19) . ?
N5 C36 1.4592(19) . ?
O9 C34 1.425(2) . ?
O9 C40 1.420(2) . ?
N10 C21 1.394(2) . ?
N10 C25 1.296(2) . ?
C18 C19 1.415(2) . ?
C18 C25 1.429(2) . ?
C18 C35 1.403(2) . ?
C19 C20 1.461(2) . ?
C19 C33 1.415(2) . ?
C20 C21 1.428(2) . ?
C20 C22 1.432(2) . ?
C21 C38 1.403(2) . ?
C22 C37 1.380(2) . ?
C23 H23 0.9300 . ?
C23 C27 1.400(2) . ?
C23 C33 1.376(2) . ?
C25 H25 0.9300 . ?
C27 H27 0.9300 . ?
C27 C35 1.368(2) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C34 1.507(2) . ?
C33 H33 0.9300 . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35 0.9300 . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 C40 1.510(2) . ?
C37 H37 0.9300 . ?
C37 C39 1.400(2) . ?
C38 H38 0.9300 . ?
C38 C39 1.363(3) . ?
C39 H39 0.9300 . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?

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
C16 O1 C32 110.87(11) . . ?
C12 N2 C3 117.68(13) . . ?
N2 C3 C6 123.38(13) . . ?
N2 C3 C28 115.74(13) . . ?
C28 C3 C6 120.88(14) . . ?
C13 N4 C15 108.88(11) . . ?
C17 N4 C13 117.02(11) . . ?
C17 N4 C15 112.45(11) . . ?
C3 C6 C8 116.94(12) . . ?
C3 C6 C17 117.18(12) . . ?
C17 C6 C8 125.86(12) . . ?
C8 C7 C12 118.52(13) . . ?
C14 C7 C8 120.94(13) . . ?
C14 C7 C12 120.43(13) . . ?
C7 C8 C6 117.35(12) . . ?
C11 C8 C6 125.69(13) . . ?
C11 C8 C7 116.85(13) . . ?
C8 C11 H11 119.5 . . ?
C29 C11 C8 121.01(13) . . ?
C29 C11 H11 119.5 . . ?
N2 C12 C7 125.21(14) . . ?
N2 C12 H12 117.4 . . ?
C7 C12 H12 117.4 . . ?
N4 C13 H13A 110.0 . . ?
N4 C13 H13B 110.0 . . ?
N4 C13 C32 108.70(12) . . ?
H13A C13 H13B 108.3 . . ?
C32 C13 H13A 110.0 . . ?
C32 C13 H13B 110.0 . . ?
C7 C14 H14 119.6 . . ?
C26 C14 C7 120.73(14) . . ?
C26 C14 H14 119.6 . . ?
N4 C15 H15A 109.6 . . ?
N4 C15 H15B 109.6 . . ?
N4 C15 C16 110.14(12) . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
O1 C16 C15 111.82(12) . . ?
O1 C16 H16A 109.3 . . ?
O1 C16 H16B 109.3 . . ?
C15 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
N4 C17 C6 119.47(12) . . ?
C24 C17 N4 120.86(13) . . ?
C24 C17 C6 119.64(13) . . ?
C17 C24 H24 119.2 . . ?
C17 C24 C31 121.70(15) . . ?
C31 C24 H24 119.2 . . ?
C14 C26 H26 120.5 . . ?
C14 C26 C29 119.09(14) . . ?
C29 C26 H26 120.5 . . ?
C3 C28 H28 119.9 . . ?
C31 C28 C3 120.12(14) . . ?
C31 C28 H28 119.9 . . ?
C11 C29 C26 121.22(14) . . ?
C11 C29 H29 119.4 . . ?
C26 C29 H29 119.4 . . ?
C24 C31 H31 120.0 . . ?
C28 C31 C24 119.94(14) . . ?
C28 C31 H31 120.0 . . ?
O1 C32 C13 111.62(13) . . ?
O1 C32 H32A 109.3 . . ?
O1 C32 H32B 109.3 . . ?
C13 C32 H32A 109.3 . . ?
C13 C32 H32B 109.3 . . ?
H32A C32 H32B 108.0 . . ?
C22 N5 C30 112.87(12) . . ?
C22 N5 C36 117.29(12) . . ?
C36 N5 C30 108.77(12) . . ?
C40 O9 C34 110.47(12) . . ?
C25 N10 C21 117.73(13) . . ?
C19 C18 C25 119.13(15) . . ?
C35 C18 C19 121.28(13) . . ?
C35 C18 C25 119.59(14) . . ?
C18 C19 C20 117.53(13) . . ?
C33 C19 C18 116.64(14) . . ?
C33 C19 C20 125.78(13) . . ?
C21 C20 C19 116.68(14) . . ?
C21 C20 C22 117.12(14) . . ?
C22 C20 C19 126.19(13) . . ?
N10 C21 C20 123.61(15) . . ?
N10 C21 C38 115.62(14) . . ?
C38 C21 C20 120.76(16) . . ?
N5 C22 C20 119.48(13) . . ?
C37 C22 N5 120.69(14) . . ?
C37 C22 C20 119.82(14) . . ?
C27 C23 H23 119.3 . . ?
C33 C23 H23 119.3 . . ?
C33 C23 C27 121.36(14) . . ?
N10 C25 C18 124.80(15) . . ?
N10 C25 H25 117.6 . . ?
C18 C25 H25 117.6 . . ?
C23 C27 H27 120.5 . . ?
C35 C27 C23 119.02(15) . . ?
C35 C27 H27 120.5 . . ?
N5 C30 H30A 109.7 . . ?
N5 C30 H30B 109.7 . . ?
N5 C30 C34 109.89(13) . . ?
H30A C30 H30B 108.2 . . ?
C34 C30 H30A 109.7 . . ?
C34 C30 H30B 109.7 . . ?
C19 C33 H33 119.5 . . ?
C23 C33 C19 120.93(14) . . ?
C23 C33 H33 119.5 . . ?
O9 C34 C30 112.01(14) . . ?
O9 C34 H34A 109.2 . . ?
O9 C34 H34B 109.2 . . ?
C30 C34 H34A 109.2 . . ?
C30 C34 H34B 109.2 . . ?
H34A C34 H34B 107.9 . . ?
C18 C35 H35 119.8 . . ?
C27 C35 C18 120.49(14) . . ?
C27 C35 H35 119.8 . . ?
N5 C36 H36A 110.0 . . ?
N5 C36 H36B 110.0 . . ?
N5 C36 C40 108.54(13) . . ?
H36A C36 H36B 108.4 . . ?
C40 C36 H36A 110.0 . . ?
C40 C36 H36B 110.0 . . ?
C22 C37 H37 119.3 . . ?
C22 C37 C39 121.34(16) . . ?
C39 C37 H37 119.3 . . ?
C21 C38 H38 119.9 . . ?
C39 C38 C21 120.28(15) . . ?
C39 C38 H38 119.9 . . ?
C37 C39 H39 119.9 . . ?
C38 C39 C37 120.15(16) . . ?
C38 C39 H39 119.9 . . ?
O9 C40 C36 111.89(15) . . ?
O9 C40 H40A 109.2 . . ?
O9 C40 H40B 109.2 . . ?
C36 C40 H40A 109.2 . . ?
C36 C40 H40B 109.2 . . ?
H40A C40 H40B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C3 C6 C8 9.08(19) . . . . ?
N2 C3 C6 C17 -172.42(12) . . . . ?
N2 C3 C28 C31 177.49(13) . . . . ?
C3 N2 C12 C7 -5.4(2) . . . . ?
C3 C6 C8 C7 -10.38(18) . . . . ?
C3 C6 C8 C11 165.74(13) . . . . ?
C3 C6 C17 N4 170.38(12) . . . . ?
C3 C6 C17 C24 -7.73(18) . . . . ?
C3 C28 C31 C24 -2.7(2) . . . . ?
N4 C13 C32 O1 -59.87(15) . . . . ?
N4 C15 C16 O1 56.19(16) . . . . ?
N4 C17 C24 C31 -175.48(13) . . . . ?
C6 C3 C28 C31 -2.8(2) . . . . ?
C6 C8 C11 C29 -178.64(13) . . . . ?
C6 C17 C24 C31 2.6(2) . . . . ?
C7 C8 C11 C29 -2.5(2) . . . . ?
C7 C14 C26 C29 -0.7(2) . . . . ?
C8 C6 C17 N4 -11.28(19) . . . . ?
C8 C6 C17 C24 170.62(13) . . . . ?
C8 C7 C12 N2 3.6(2) . . . . ?
C8 C7 C14 C26 -3.0(2) . . . . ?
C8 C11 C29 C26 -1.1(2) . . . . ?
C12 N2 C3 C6 -1.2(2) . . . . ?
C12 N2 C3 C28 178.48(13) . . . . ?
C12 C7 C8 C6 4.74(18) . . . . ?
C12 C7 C8 C11 -171.73(12) . . . . ?
C12 C7 C14 C26 173.18(14) . . . . ?
C13 N4 C15 C16 -58.38(15) . . . . ?
C13 N4 C17 C6 158.63(12) . . . . ?
C13 N4 C17 C24 -23.29(18) . . . . ?
C14 C7 C8 C6 -179.03(12) . . . . ?
C14 C7 C8 C11 4.50(19) . . . . ?
C14 C7 C12 N2 -172.67(14) . . . . ?
C14 C26 C29 C11 2.7(2) . . . . ?
C15 N4 C13 C32 59.71(15) . . . . ?
C15 N4 C17 C6 -74.23(15) . . . . ?
C15 N4 C17 C24 103.85(14) . . . . ?
C16 O1 C32 C13 57.22(16) . . . . ?
C17 N4 C13 C32 -171.43(11) . . . . ?
C17 N4 C15 C16 170.26(11) . . . . ?
C17 C6 C8 C7 171.27(12) . . . . ?
C17 C6 C8 C11 -12.6(2) . . . . ?
C17 C24 C31 C28 2.8(2) . . . . ?
C28 C3 C6 C8 -170.58(12) . . . . ?
C28 C3 C6 C17 7.91(19) . . . . ?
C32 O1 C16 C15 -55.10(17) . . . . ?
N5 C22 C37 C39 -176.12(14) . . . . ?
N5 C30 C34 O9 56.51(18) . . . . ?
N5 C36 C40 O9 -60.17(18) . . . . ?
N10 C21 C38 C39 179.33(14) . . . . ?
C18 C19 C20 C21 -7.99(19) . . . . ?
C18 C19 C20 C22 173.29(14) . . . . ?
C18 C19 C33 C23 -4.2(2) . . . . ?
C19 C18 C25 N10 1.9(2) . . . . ?
C19 C18 C35 C27 -2.2(2) . . . . ?
C19 C20 C21 N10 7.4(2) . . . . ?
C19 C20 C21 C38 -171.69(13) . . . . ?
C19 C20 C22 N5 -10.0(2) . . . . ?
C19 C20 C22 C37 170.95(14) . . . . ?
C20 C19 C33 C23 178.36(14) . . . . ?
C20 C21 C38 C39 -1.5(2) . . . . ?
C20 C22 C37 C39 2.9(2) . . . . ?
C21 N10 C25 C18 -3.0(2) . . . . ?
C21 C20 C22 N5 171.28(13) . . . . ?
C21 C20 C22 C37 -7.8(2) . . . . ?
C21 C38 C39 C37 -3.7(2) . . . . ?
C22 N5 C30 C34 169.55(13) . . . . ?
C22 N5 C36 C40 -170.76(13) . . . . ?
C22 C20 C21 N10 -173.79(13) . . . . ?
C22 C20 C21 C38 7.2(2) . . . . ?
C22 C37 C39 C38 3.0(2) . . . . ?
C23 C27 C35 C18 -2.4(2) . . . . ?
C25 N10 C21 C20 -1.9(2) . . . . ?
C25 N10 C21 C38 177.19(14) . . . . ?
C25 C18 C19 C20 3.9(2) . . . . ?
C25 C18 C19 C33 -173.79(13) . . . . ?
C25 C18 C35 C27 177.01(15) . . . . ?
C27 C23 C33 C19 -0.3(2) . . . . ?
C30 N5 C22 C20 -72.68(16) . . . . ?
C30 N5 C22 C37 106.36(16) . . . . ?
C30 N5 C36 C40 59.65(17) . . . . ?
C33 C19 C20 C21 169.43(14) . . . . ?
C33 C19 C20 C22 -9.3(2) . . . . ?
C33 C23 C27 C35 3.7(3) . . . . ?
C34 O9 C40 C36 57.4(2) . . . . ?
C35 C18 C19 C20 -176.89(13) . . . . ?
C35 C18 C19 C33 5.5(2) . . . . ?
C35 C18 C25 N10 -177.37(15) . . . . ?
C36 N5 C22 C20 159.69(13) . . . . ?
C36 N5 C22 C37 -21.3(2) . . . . ?
C36 N5 C30 C34 -58.47(16) . . . . ?
C40 O9 C34 C30 -55.45(19) . . . . ?

_olex2_date_sample_data_collection 2019-06-26
_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 2.401
_oxdiff_exptl_absorpt_empirical_full_min 0.837
