# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_RGYYC477
_database_code_depnum_ccdc_archive 'CCDC 1910244'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;CNRS
France
;
_audit_update_record             
;
2019-04-15 deposited with the CCDC.	2019-07-23 downloaded from the CCDC.
;


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H15 N O3'
_chemical_formula_sum            'C21 H15 N O3'
_chemical_formula_weight         329.34
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                            UNIT CELL INFORMATION                             #
#------------------------------------------------------------------------------#


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.076(4)
_cell_length_b                   8.828(3)
_cell_length_c                   11.834(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.487(10)
_cell_angle_gamma                90
_cell_volume                     1633.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    2248
_cell_measurement_theta_min      2.6058
_cell_measurement_theta_max      27.6383
_cell_measurement_wavelength     0.71073

#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.050
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             688
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.746
_exptl_absorpt_correction_T_max  0.996

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_reflns_av_r_equivalents  0.0909
_diffrn_reflns_av_uneti/neti     0.0769
_diffrn_reflns_number            8256
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.606
_diffrn_reflns_theta_max         27.751
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.977
_reflns_number_total             1874
_reflns_number_gt                1082
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0915P)²+2.5744P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018_3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.008(2)
_refine_ls_number_reflns         1874
_refine_ls_number_parameters     113
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1441
_refine_ls_R_factor_gt           0.0841
_refine_ls_wR_factor_ref         0.2340
_refine_ls_wR_factor_gt          0.2021
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.047

#...............................................................................
# .RES SHELXL file: j2.res
#...............................................................................



# ............... End of .HKL file ........................................... #
#------------------------------------------------------------------------------#
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1A O 0.63680(16) 0.6415(3) 0.2133(2) 0.0667(9) Uani 0.5 1 d . . P A 1
C2A C 0.6186(2) 0.6704(5) 0.3050(3) 0.0560(10) Uani 0.5 1 d . . P A 1
C3A C 0.64952(14) 0.7977(3) 0.38144(17) 0.0546(10) Uani 0.5 1 d G . P A 1
C4A C 0.71011(13) 0.9017(3) 0.36355(16) 0.0594(11) Uani 0.5 1 d G . P A 1
H4A H 0.734309 0.891961 0.297938 0.071 Uiso 0.5 1 calc R U P A 1
C5A C 0.73530(14) 1.0198(3) 0.44166(19) 0.0654(13) Uani 0.5 1 d G . P A 1
H5A H 0.776711 1.090890 0.429430 0.079 Uiso 0.5 1 calc R U P A 1
C6A C 0.69989(17) 1.0341(3) 0.53766(19) 0.0744(14) Uani 0.5 1 d G . P A 1
H6A H 0.717108 1.114823 0.591045 0.089 Uiso 0.5 1 calc R U P A 1
C7A C 0.63930(16) 0.9301(4) 0.55556(17) 0.0841(16) Uani 0.5 1 d G . P A 1
H7A H 0.615103 0.939829 0.621170 0.101 Uiso 0.5 1 calc R U P A 1
C8A C 0.61411(14) 0.8119(3) 0.47745(19) 0.0728(14) Uani 0.5 1 d G . P A 1
C9A C 0.5646(4) 0.6543(9) 0.4584(5) 0.0508(18) Uani 0.5 1 d . . P A 1
H9A H 0.591252 0.584974 0.522458 0.061 Uiso 0.5 1 calc R U P A 1
H9B H 0.504708 0.671320 0.463286 0.061 Uiso 0.5 1 calc R U P A 1
N10A N 0.56438(16) 0.5846(3) 0.3542(2) 0.0530(8) Uani 0.5 1 d . . P A 1
C11A C 0.53228(18) 0.4492(4) 0.3010(2) 0.0435(9) Uani 0.5 1 d . . P A 1
C12A C 0.56281(19) 0.3143(5) 0.3515(3) 0.0561(10) Uani 0.5 1 d . . P A 1
H12A H 0.606123 0.314084 0.421492 0.067 Uiso 0.5 1 calc R U P A 1
C13A C 0.5313(2) 0.1798(5) 0.3016(4) 0.0669(12) Uani 0.5 1 d . . P A 1
H13A H 0.552(3) 0.091(5) 0.336(4) 0.080 Uiso 0.5 1 d . U P B 1
O1B O 0.63680(16) 0.6415(3) 0.2133(2) 0.0667(9) Uani 0.5 1 d . . P C 2
C2B C 0.6186(2) 0.6704(5) 0.3050(3) 0.0560(10) Uani 0.5 1 d . . P C 2
C3B C 0.64952(14) 0.7977(3) 0.38144(17) 0.0546(10) Uani 0.5 1 d G . P C 2
C4B C 0.71011(13) 0.9017(3) 0.36355(16) 0.0594(11) Uani 0.5 1 d G . P C 2
H4B H 0.734309 0.891961 0.297938 0.071 Uiso 0.5 1 calc R U P C 2
C5B C 0.73530(14) 1.0198(3) 0.44166(19) 0.0654(13) Uani 0.5 1 d G . P C 2
H5B H 0.776711 1.090890 0.429430 0.079 Uiso 0.5 1 calc R U P C 2
C6B C 0.69989(17) 1.0341(3) 0.53766(19) 0.0744(14) Uani 0.5 1 d G . P C 2
H6B H 0.717108 1.114823 0.591045 0.089 Uiso 0.5 1 calc R U P C 2
C7B C 0.63930(16) 0.9301(4) 0.55556(17) 0.0841(16) Uani 0.5 1 d G . P C 2
H7B H 0.615103 0.939829 0.621170 0.101 Uiso 0.5 1 calc R U P C 2
C8B C 0.61411(14) 0.8119(3) 0.47745(19) 0.0728(14) Uani 0.5 1 d G . P C 2
H8B H 0.572700 0.740898 0.489680 0.087 Uiso 0.5 1 calc R U P C 2
O10B O 0.56438(16) 0.5846(3) 0.3542(2) 0.0530(8) Uani 0.5 1 d . . P C 2
C11B C 0.53228(18) 0.4492(4) 0.3010(2) 0.0435(9) Uani 0.5 1 d . . P C 2
C12B C 0.56281(19) 0.3143(5) 0.3515(3) 0.0561(10) Uani 0.5 1 d . . P C 2
H12B H 0.606123 0.314084 0.421492 0.067 Uiso 0.5 1 calc R U P C 2
C13B C 0.5313(2) 0.1798(5) 0.3016(4) 0.0669(12) Uani 0.5 1 d . . P C 2
H13B H 0.552(3) 0.091(5) 0.336(4) 0.080 Uiso 0.5 1 d . U P D 2



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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
O1A C2A 1.216(4) . ?
C2A N10A 1.382(5) . ?
C2A C3A 1.455(4) . ?
C3A C4A 1.3900 . ?
C3A C8A 1.3900 . ?
C4A C5A 1.3900 . ?
C4A H4A 0.9500 . ?
C5A C6A 1.3900 . ?
C5A H5A 0.9500 . ?
C6A C7A 1.3900 . ?
C6A H6A 0.9500 . ?
C7A C8A 1.3900 . ?
C7A H7A 0.9500 . ?
C8A C9A 1.593(7) . ?
C9A N10A 1.378(7) . ?
C9A H9A 0.9900 . ?
C9A H9B 0.9900 . ?
N10A C11A 1.393(4) . ?
C11A C12A 1.371(5) . ?
C11A C11A 1.396(5) 2_655 ?
C12A C13A 1.370(6) . ?
C12A H12A 0.9500 . ?
C13A C13A 1.389(7) 2_655 ?
C13A H13A 0.91(5) . ?
O1B C2B 1.216(4) . ?
C2B O10B 1.382(5) . ?
C2B C3B 1.455(4) . ?
C3B C4B 1.3900 . ?
C3B C8B 1.3900 . ?
C4B C5B 1.3900 . ?
C4B H4B 0.9500 . ?
C5B C6B 1.3900 . ?
C5B H5B 0.9500 . ?
C6B C7B 1.3900 . ?
C6B H6B 0.9500 . ?
C7B C8B 1.3900 . ?
C7B H7B 0.9500 . ?
C8B H8B 0.9500 . ?
O10B C11B 1.393(4) . ?
C11B C12B 1.371(5) . ?
C12B C13B 1.370(6) . ?
C12B H12B 0.9500 . ?
C13B H13B 0.91(5) . ?

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
O1A C2A N10A 124.6(4) . . ?
O1A C2A C3A 126.8(3) . . ?
N10A C2A C3A 108.6(3) . . ?
C4A C3A C8A 120.0 . . ?
C4A C3A C2A 124.4(2) . . ?
C8A C3A C2A 115.6(2) . . ?
C5A C4A C3A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C4A C5A C6A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C7A C6A C5A 120.0 . . ?
C7A C6A H6A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
C6A C7A C8A 120.0 . . ?
C6A C7A H7A 120.0 . . ?
C8A C7A H7A 120.0 . . ?
C7A C8A C3A 120.0 . . ?
C7A C8A C9A 143.9(3) . . ?
C3A C8A C9A 95.3(3) . . ?
N10A C9A C8A 114.4(4) . . ?
N10A C9A H9A 108.6 . . ?
C8A C9A H9A 108.6 . . ?
N10A C9A H9B 108.6 . . ?
C8A C9A H9B 108.6 . . ?
H9A C9A H9B 107.6 . . ?
C9A N10A C2A 105.1(4) . . ?
C9A N10A C11A 135.3(4) . . ?
C2A N10A C11A 119.0(3) . . ?
C12A C11A N10A 119.4(3) . . ?
C12A C11A C11A 119.68(19) . 2_655 ?
N10A C11A C11A 120.86(16) . 2_655 ?
C13A C12A C11A 120.4(3) . . ?
C13A C12A H12A 119.8 . . ?
C11A C12A H12A 119.8 . . ?
C12A C13A C13A 119.9(2) . 2_655 ?
C12A C13A H13A 119(3) . . ?
C13A C13A H13A 121(3) 2_655 . ?
O1B C2B O10B 124.6(4) . . ?
O1B C2B C3B 126.8(3) . . ?
O10B C2B C3B 108.6(3) . . ?
C4B C3B C8B 120.0 . . ?
C4B C3B C2B 124.4(2) . . ?
C8B C3B C2B 115.6(2) . . ?
C5B C4B C3B 120.0 . . ?
C5B C4B H4B 120.0 . . ?
C3B C4B H4B 120.0 . . ?
C4B C5B C6B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
C6B C5B H5B 120.0 . . ?
C7B C6B C5B 120.0 . . ?
C7B C6B H6B 120.0 . . ?
C5B C6B H6B 120.0 . . ?
C6B C7B C8B 120.0 . . ?
C6B C7B H7B 120.0 . . ?
C8B C7B H7B 120.0 . . ?
C7B C8B C3B 120.0 . . ?
C7B C8B H8B 120.0 . . ?
C3B C8B H8B 120.0 . . ?
C2B O10B C11B 119.0(3) . . ?
C12B C11B O10B 119.4(3) . . ?
C13B C12B C11B 120.4(3) . . ?
C13B C12B H12B 119.8 . . ?
C11B C12B H12B 119.8 . . ?
C12B C13B H13B 119(3) . . ?

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
O1A C2A C3A C4A -4.5(5) . . . . ?
N10A C2A C3A C4A 175.22(19) . . . . ?
O1A C2A C3A C8A 175.4(3) . . . . ?
N10A C2A C3A C8A -4.9(3) . . . . ?
C8A C3A C4A C5A 0.0 . . . . ?
C2A C3A C4A C5A 179.9(3) . . . . ?
C3A C4A C5A C6A 0.0 . . . . ?
C4A C5A C6A C7A 0.0 . . . . ?
C5A C6A C7A C8A 0.0 . . . . ?
C6A C7A C8A C3A 0.0 . . . . ?
C6A C7A C8A C9A 166.5(5) . . . . ?
C4A C3A C8A C7A 0.0 . . . . ?
C2A C3A C8A C7A -179.9(2) . . . . ?
C4A C3A C8A C9A -172.1(3) . . . . ?
C2A C3A C8A C9A 8.1(3) . . . . ?
C7A C8A C9A N10A -177.8(2) . . . . ?
C3A C8A C9A N10A -9.6(5) . . . . ?
C8A C9A N10A C2A 7.4(6) . . . . ?
C8A C9A N10A C11A 178.5(3) . . . . ?
O1A C2A N10A C9A 177.8(4) . . . . ?
C3A C2A N10A C9A -1.9(4) . . . . ?
O1A C2A N10A C11A 4.9(5) . . . . ?
C3A C2A N10A C11A -174.8(2) . . . . ?
C9A N10A C11A C12A -63.0(6) . . . . ?
C2A N10A C11A C12A 107.1(3) . . . . ?
C9A N10A C11A C11A 115.1(6) . . . 2_655 ?
C2A N10A C11A C11A -74.8(4) . . . 2_655 ?
N10A C11A C12A C13A 179.1(3) . . . . ?
C11A C11A C12A C13A 1.0(6) 2_655 . . . ?
C11A C12A C13A C13A 0.8(8) . . . 2_655 ?
O1B C2B C3B C4B -4.5(5) . . . . ?
O10B C2B C3B C4B 175.22(19) . . . . ?
O1B C2B C3B C8B 175.4(3) . . . . ?
O10B C2B C3B C8B -4.9(3) . . . . ?
C8B C3B C4B C5B 0.0 . . . . ?
C2B C3B C4B C5B 179.9(3) . . . . ?
C3B C4B C5B C6B 0.0 . . . . ?
C4B C5B C6B C7B 0.0 . . . . ?
C5B C6B C7B C8B 0.0 . . . . ?
C6B C7B C8B C3B 0.0 . . . . ?
C4B C3B C8B C7B 0.0 . . . . ?
C2B C3B C8B C7B -179.9(2) . . . . ?
O1B C2B O10B C11B 4.9(5) . . . . ?
C3B C2B O10B C11B -174.8(2) . . . . ?
C2B O10B C11B C12B 107.1(3) . . . . ?
O10B C11B C12B C13B 179.1(3) . . . . ?

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR RGYYC477                                               #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
####################################################################### 
# 
# 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_YYC4128
_database_code_depnum_ccdc_archive 'CCDC 1910245'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;CNRS
France
;
_audit_update_record             
;
2019-04-15 deposited with the CCDC.	2019-07-23 downloaded from the CCDC.
;


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H17 N O3'
_chemical_formula_sum            'C22 H17 N O3'
_chemical_formula_weight         343.36
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                            UNIT CELL INFORMATION                             #
#------------------------------------------------------------------------------#


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
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                   8.6965(7)
_cell_length_b                   10.6905(7)
_cell_length_c                   18.5537(14)
_cell_angle_alpha                90
_cell_angle_beta                 96.339(3)
_cell_angle_gamma                90
_cell_volume                     1714.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    9949
_cell_measurement_theta_min      2.9174
_cell_measurement_theta_max      27.4790
_cell_measurement_wavelength     0.71073

#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             720
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_T_max  0.976

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_diffrn_reflns_av_r_equivalents  0.0376
_diffrn_reflns_av_uneti/neti     0.0277
_diffrn_reflns_number            24131
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.202
_diffrn_reflns_theta_max         27.512
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_reflns_number_total             3912
_reflns_number_gt                3437
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0503P)²+0.8477P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018_3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.021(3)
_refine_ls_number_reflns         3912
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1096
_refine_ls_wR_factor_gt          0.1047
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.045

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................



# ............... End of .HKL file ........................................... #
#------------------------------------------------------------------------------#
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.59206(11) 0.26479(9) 0.74585(5) 0.0288(2) Uani 1 1 d . . . . .
C2 C 0.56138(14) 0.17734(12) 0.70432(6) 0.0223(3) Uani 1 1 d . . . . .
C3 C 0.66171(14) 0.11732(12) 0.65502(6) 0.0223(3) Uani 1 1 d . . . . .
C4 C 0.81362(15) 0.14638(13) 0.64445(7) 0.0270(3) Uani 1 1 d . . . . .
H4 H 0.868010 0.211645 0.671053 0.032 Uiso 1 1 calc R U . . .
C5 C 0.88294(16) 0.07691(14) 0.59381(8) 0.0319(3) Uani 1 1 d . . . . .
H5 H 0.986555 0.094548 0.585443 0.038 Uiso 1 1 calc R U . . .
C6 C 0.80204(16) -0.01843(14) 0.55514(7) 0.0312(3) Uani 1 1 d . . . . .
H6 H 0.851036 -0.064358 0.520250 0.037 Uiso 1 1 calc R U . . .
C7 C 0.65071(16) -0.04776(13) 0.56662(7) 0.0272(3) Uani 1 1 d . . . . .
H7 H 0.596306 -0.113311 0.540288 0.033 Uiso 1 1 calc R U . . .
C8 C 0.58129(14) 0.02135(12) 0.61759(6) 0.0225(3) Uani 1 1 d . . . . .
C9 C 0.42288(14) 0.01044(12) 0.64240(7) 0.0236(3) Uani 1 1 d . . . . .
H9A H 0.340744 0.021332 0.601491 0.028 Uiso 1 1 calc R U . . .
H9B H 0.408986 -0.071262 0.665947 0.028 Uiso 1 1 calc R U . . .
N10 N 0.42281(12) 0.11372(10) 0.69453(5) 0.0216(2) Uani 1 1 d . . . . .
C11 C 0.29571(14) 0.14116(12) 0.73364(6) 0.0214(3) Uani 1 1 d . . . . .
C12 C 0.22879(14) 0.04922(12) 0.77365(7) 0.0239(3) Uani 1 1 d . . . . .
H12 H 0.264351 -0.034713 0.772626 0.029 Uiso 1 1 calc R U . . .
C13 C 0.11043(14) 0.08012(13) 0.81492(7) 0.0258(3) Uani 1 1 d . . . . .
H13 H 0.064293 0.016138 0.840821 0.031 Uiso 1 1 calc R U . . .
C14 C 0.05780(14) 0.20247(13) 0.81925(7) 0.0254(3) Uani 1 1 d . . . . .
C15 C -0.06811(17) 0.23695(15) 0.86539(8) 0.0359(3) Uani 1 1 d . . . . .
H15A H -0.169388 0.222113 0.837993 0.054 Uiso 1 1 calc R U . . .
H15B H -0.058608 0.325533 0.878734 0.054 Uiso 1 1 calc R U . . .
H15C H -0.058146 0.185611 0.909415 0.054 Uiso 1 1 calc R U . . .
C16 C 0.12179(15) 0.29322(12) 0.77753(7) 0.0250(3) Uani 1 1 d . . . . .
H16 H 0.086976 0.377343 0.778748 0.030 Uiso 1 1 calc R U . . .
C17 C 0.23550(14) 0.26140(12) 0.73445(6) 0.0224(3) Uani 1 1 d . . . . .
O18 O 0.29011(10) 0.35691(8) 0.69231(5) 0.0243(2) Uani 1 1 d . . . . .
C19 C 0.25174(16) 0.34925(12) 0.61950(7) 0.0269(3) Uani 1 1 d . . . . .
O20 O 0.18446(16) 0.26176(11) 0.58990(6) 0.0506(4) Uani 1 1 d . . . . .
C21 C 0.30327(14) 0.46196(12) 0.58252(6) 0.0229(3) Uani 1 1 d . . . . .
C22 C 0.40656(15) 0.54592(12) 0.61814(7) 0.0256(3) Uani 1 1 d . . . . .
H22 H 0.448264 0.530683 0.666849 0.031 Uiso 1 1 calc R U . . .
C23 C 0.44880(17) 0.65223(14) 0.58241(7) 0.0332(3) Uani 1 1 d . . . . .
H23 H 0.520455 0.709651 0.606435 0.040 Uiso 1 1 calc R U . . .
C24 C 0.38655(19) 0.67467(14) 0.51176(7) 0.0356(3) Uani 1 1 d . . . . .
H24 H 0.414051 0.748433 0.487666 0.043 Uiso 1 1 calc R U . . .
C25 C 0.2849(2) 0.59060(15) 0.47616(8) 0.0426(4) Uani 1 1 d . . . . .
H25 H 0.243362 0.606196 0.427459 0.051 Uiso 1 1 calc R U . . .
C26 C 0.2430(2) 0.48362(14) 0.51100(7) 0.0375(4) Uani 1 1 d . . . . .
H26 H 0.173572 0.425289 0.486287 0.045 Uiso 1 1 calc R U . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.2221(15) . ?
C2 N10 1.3782(15) . ?
C2 C3 1.4784(18) . ?
C3 C8 1.3844(17) . ?
C3 C4 1.3919(18) . ?
C4 C5 1.387(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.3920(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.3896(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.5044(17) . ?
C9 N10 1.4679(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N10 C11 1.4183(16) . ?
C11 C17 1.3887(18) . ?
C11 C12 1.3968(17) . ?
C12 C13 1.3888(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(2) . ?
C13 H13 0.9500 . ?
C14 C16 1.3947(18) . ?
C14 C15 1.5082(19) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.3809(18) . ?
C16 H16 0.9500 . ?
C17 O18 1.4005(14) . ?
O18 C19 1.3576(15) . ?
C19 O20 1.2033(17) . ?
C19 C21 1.4804(17) . ?
C21 C22 1.3849(17) . ?
C21 C26 1.3912(18) . ?
C22 C23 1.3855(18) . ?
C22 H22 0.9500 . ?
C23 C24 1.3828(19) . ?
C23 H23 0.9500 . ?
C24 C25 1.377(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C2 N10 125.98(12) . . ?
O1 C2 C3 128.27(11) . . ?
N10 C2 C3 105.75(10) . . ?
C8 C3 C4 121.97(12) . . ?
C8 C3 C2 109.39(11) . . ?
C4 C3 C2 128.64(12) . . ?
C5 C4 C3 117.79(12) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
C4 C5 C6 120.58(12) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C7 121.24(13) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 118.26(12) . . ?
C8 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
C3 C8 C7 120.14(12) . . ?
C3 C8 C9 109.45(11) . . ?
C7 C8 C9 130.41(11) . . ?
N10 C9 C8 102.14(9) . . ?
N10 C9 H9A 111.3 . . ?
C8 C9 H9A 111.3 . . ?
N10 C9 H9B 111.3 . . ?
C8 C9 H9B 111.3 . . ?
H9A C9 H9B 109.2 . . ?
C2 N10 C11 123.37(10) . . ?
C2 N10 C9 113.21(10) . . ?
C11 N10 C9 123.35(10) . . ?
C17 C11 C12 117.76(11) . . ?
C17 C11 N10 120.87(11) . . ?
C12 C11 N10 121.36(11) . . ?
C13 C12 C11 120.22(12) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 121.61(12) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C16 117.90(12) . . ?
C13 C14 C15 121.79(12) . . ?
C16 C14 C15 120.28(13) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C14 120.33(12) . . ?
C17 C16 H16 119.8 . . ?
C14 C16 H16 119.8 . . ?
C16 C17 C11 121.96(11) . . ?
C16 C17 O18 116.89(11) . . ?
C11 C17 O18 121.15(11) . . ?
C19 O18 C17 116.76(9) . . ?
O20 C19 O18 123.70(12) . . ?
O20 C19 C21 125.31(12) . . ?
O18 C19 C21 111.00(10) . . ?
C22 C21 C26 120.23(12) . . ?
C22 C21 C19 121.33(11) . . ?
C26 C21 C19 118.43(11) . . ?
C21 C22 C23 119.71(12) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C24 C23 C22 119.94(13) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C25 C24 C23 120.32(13) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 120.26(13) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C21 119.53(13) . . ?
C25 C26 H26 120.2 . . ?
C21 C26 H26 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C8 179.92(12) . . . . ?
N10 C2 C3 C8 0.20(13) . . . . ?
O1 C2 C3 C4 -0.1(2) . . . . ?
N10 C2 C3 C4 -179.78(12) . . . . ?
C8 C3 C4 C5 0.99(19) . . . . ?
C2 C3 C4 C5 -179.03(12) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C4 C5 C6 C7 -0.7(2) . . . . ?
C5 C6 C7 C8 0.4(2) . . . . ?
C4 C3 C8 C7 -1.32(19) . . . . ?
C2 C3 C8 C7 178.69(11) . . . . ?
C4 C3 C8 C9 178.22(11) . . . . ?
C2 C3 C8 C9 -1.76(14) . . . . ?
C6 C7 C8 C3 0.59(19) . . . . ?
C6 C7 C8 C9 -178.85(13) . . . . ?
C3 C8 C9 N10 2.50(13) . . . . ?
C7 C8 C9 N10 -178.01(13) . . . . ?
O1 C2 N10 C11 -1.27(19) . . . . ?
C3 C2 N10 C11 178.45(10) . . . . ?
O1 C2 N10 C9 -178.20(12) . . . . ?
C3 C2 N10 C9 1.52(13) . . . . ?
C8 C9 N10 C2 -2.47(13) . . . . ?
C8 C9 N10 C11 -179.40(10) . . . . ?
C2 N10 C11 C17 54.61(16) . . . . ?
C9 N10 C11 C17 -128.77(13) . . . . ?
C2 N10 C11 C12 -124.16(13) . . . . ?
C9 N10 C11 C12 52.46(16) . . . . ?
C17 C11 C12 C13 -2.62(17) . . . . ?
N10 C11 C12 C13 176.19(11) . . . . ?
C11 C12 C13 C14 -1.62(19) . . . . ?
C12 C13 C14 C16 3.45(18) . . . . ?
C12 C13 C14 C15 -178.54(12) . . . . ?
C13 C14 C16 C17 -1.02(18) . . . . ?
C15 C14 C16 C17 -179.06(12) . . . . ?
C14 C16 C17 C11 -3.32(19) . . . . ?
C14 C16 C17 O18 177.88(11) . . . . ?
C12 C11 C17 C16 5.11(18) . . . . ?
N10 C11 C17 C16 -173.71(11) . . . . ?
C12 C11 C17 O18 -176.15(10) . . . . ?
N10 C11 C17 O18 5.04(17) . . . . ?
C16 C17 O18 C19 -110.13(13) . . . . ?
C11 C17 O18 C19 71.06(15) . . . . ?
C17 O18 C19 O20 -5.5(2) . . . . ?
C17 O18 C19 C21 174.32(10) . . . . ?
O20 C19 C21 C22 -166.61(15) . . . . ?
O18 C19 C21 C22 13.53(18) . . . . ?
O20 C19 C21 C26 14.7(2) . . . . ?
O18 C19 C21 C26 -165.18(13) . . . . ?
C26 C21 C22 C23 0.5(2) . . . . ?
C19 C21 C22 C23 -178.18(13) . . . . ?
C21 C22 C23 C24 0.7(2) . . . . ?
C22 C23 C24 C25 -1.2(3) . . . . ?
C23 C24 C25 C26 0.6(3) . . . . ?
C24 C25 C26 C21 0.5(3) . . . . ?
C22 C21 C26 C25 -1.1(2) . . . . ?
C19 C21 C26 C25 177.60(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C9 H9B O1 0.99 2.40 3.3573(16) 162.9 2_646 yes
C12 H12 O1 0.95 2.52 3.4538(16) 166.5 2_646 yes

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR YYC4128                                                #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
####################################################################### 
# 
# 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_YYC499
_database_code_depnum_ccdc_archive 'CCDC 1910246'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;CNRS
France
;
_audit_update_record             
;
2019-04-15 deposited with the CCDC.	2019-07-23 downloaded from the CCDC.
;


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H17 N O4'
_chemical_formula_sum            'C22 H17 N O4'
_chemical_formula_weight         359.36
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                            UNIT CELL INFORMATION                             #
#------------------------------------------------------------------------------#


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

_cell_length_a                   11.7123(12)
_cell_length_b                   11.9264(14)
_cell_length_c                   14.1370(15)
_cell_angle_alpha                88.483(4)
_cell_angle_beta                 70.167(4)
_cell_angle_gamma                75.429(4)
_cell_volume                     1794.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    9529
_cell_measurement_theta_min      2.4151
_cell_measurement_theta_max      27.5158
_cell_measurement_wavelength     0.71073

#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.260
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             752
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_T_max  0.976

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_diffrn_reflns_av_r_equivalents  0.0382
_diffrn_reflns_av_uneti/neti     0.0340
_diffrn_reflns_number            34079
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.245
_diffrn_reflns_theta_max         27.546
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_reflns_number_total             8226
_reflns_number_gt                6808
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0171P)²+2.2637P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8226
_refine_ls_number_parameters     489
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.0901
_refine_ls_wR_factor_gt          0.0824
_refine_ls_goodness_of_fit_ref   0.817
_refine_ls_restrained_S_all      0.817
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.050

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................



# ............... End of .HKL file ........................................... #
#------------------------------------------------------------------------------#
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.04389(9) 1.14462(8) 0.69723(8) 0.0227(2) Uani 1 1 d . . . . .
C2 C -0.02677(12) 1.08020(11) 0.72360(10) 0.0171(3) Uani 1 1 d . . . . .
C3 C -0.14895(12) 1.10044(11) 0.80725(10) 0.0169(2) Uani 1 1 d . . . . .
C4 C -0.20803(13) 1.19160(12) 0.88087(11) 0.0226(3) Uani 1 1 d . . . . .
H4 H -0.170248 1.252751 0.883208 0.027 Uiso 1 1 calc R U . . .
C5 C -0.32447(14) 1.18997(13) 0.95095(11) 0.0245(3) Uani 1 1 d . . . . .
H5 H -0.366776 1.250442 1.002664 0.029 Uiso 1 1 calc R U . . .
C6 C -0.37959(13) 1.10047(12) 0.94598(10) 0.0230(3) Uani 1 1 d . . . . .
H6 H -0.459505 1.101339 0.994118 0.028 Uiso 1 1 calc R U . . .
C7 C -0.31993(13) 1.00993(12) 0.87196(10) 0.0210(3) Uani 1 1 d . . . . .
H7 H -0.358237 0.949418 0.868764 0.025 Uiso 1 1 calc R U . . .
C8 C -0.20293(12) 1.01028(11) 0.80285(10) 0.0169(2) Uani 1 1 d . . . . .
C9 C -0.11626(12) 0.92397(11) 0.71766(10) 0.0184(3) Uani 1 1 d . . . . .
H9A H -0.092351 0.845987 0.742065 0.022 Uiso 1 1 calc R U . . .
H9B H -0.154859 0.918665 0.666098 0.022 Uiso 1 1 calc R U . . .
N10 N -0.00760(10) 0.97367(9) 0.67791(8) 0.0164(2) Uani 1 1 d . . . . .
C11 C 0.10079(12) 0.91853(11) 0.59578(10) 0.0159(2) Uani 1 1 d . . . . .
C12 C 0.09015(12) 0.87271(11) 0.51087(10) 0.0178(3) Uani 1 1 d . . . . .
H12 H 0.009042 0.879580 0.507526 0.021 Uiso 1 1 calc R U . . .
C13 C 0.19592(13) 0.81684(11) 0.43041(10) 0.0186(3) Uani 1 1 d . . . . .
H13 H 0.187066 0.785078 0.373151 0.022 Uiso 1 1 calc R U . . .
C14 C 0.31439(12) 0.80812(11) 0.43490(10) 0.0188(3) Uani 1 1 d . . . . .
O15 O 0.42453(9) 0.75519(9) 0.36087(8) 0.0265(2) Uani 1 1 d . . . . .
C16 C 0.41723(15) 0.70515(14) 0.27328(11) 0.0300(3) Uani 1 1 d . . . . .
H16A H 0.368985 0.646873 0.292975 0.045 Uiso 1 1 calc R U . . .
H16B H 0.502141 0.668164 0.227474 0.045 Uiso 1 1 calc R U . . .
H16C H 0.375533 0.766016 0.239196 0.045 Uiso 1 1 calc R U . . .
C17 C 0.32757(12) 0.85170(11) 0.52017(10) 0.0196(3) Uani 1 1 d . . . . .
H17 H 0.408708 0.845013 0.523386 0.024 Uiso 1 1 calc R U . . .
C18 C 0.22148(12) 0.90459(11) 0.59971(10) 0.0169(2) Uani 1 1 d . . . . .
O19 O 0.22772(9) 0.93735(8) 0.69175(7) 0.01907(19) Uani 1 1 d . . . . .
C20 C 0.29688(12) 1.01401(11) 0.69303(10) 0.0177(3) Uani 1 1 d . . . . .
O21 O 0.36970(9) 1.04036(9) 0.61854(7) 0.0246(2) Uani 1 1 d . . . . .
C22 C 0.26889(12) 1.06014(11) 0.79727(10) 0.0184(3) Uani 1 1 d . . . . .
C23 C 0.34848(13) 1.12148(12) 0.81287(11) 0.0217(3) Uani 1 1 d . . . . .
H23 H 0.422752 1.125571 0.759498 0.026 Uiso 1 1 calc R U . . .
C24 C 0.31893(14) 1.17653(13) 0.90652(11) 0.0254(3) Uani 1 1 d . . . . .
H24 H 0.373256 1.218004 0.917444 0.031 Uiso 1 1 calc R U . . .
C25 C 0.20991(15) 1.17102(13) 0.98434(11) 0.0275(3) Uani 1 1 d . . . . .
H25 H 0.189096 1.209978 1.048046 0.033 Uiso 1 1 calc R U . . .
C26 C 0.13168(15) 1.10915(14) 0.96948(11) 0.0295(3) Uani 1 1 d . . . . .
H26 H 0.057470 1.105403 1.023081 0.035 Uiso 1 1 calc R U . . .
C27 C 0.16108(14) 1.05240(13) 0.87648(11) 0.0249(3) Uani 1 1 d . . . . .
H27 H 0.108109 1.008526 0.866769 0.030 Uiso 1 1 calc R U . . .
O51 O 0.04343(9) 0.33332(8) 0.19377(7) 0.0226(2) Uani 1 1 d . . . . .
C52 C -0.02333(12) 0.43253(11) 0.21925(10) 0.0169(2) Uani 1 1 d . . . . .
C53 C -0.14219(12) 0.47207(11) 0.30551(10) 0.0174(3) Uani 1 1 d . . . . .
C54 C -0.20080(13) 0.40873(12) 0.38236(11) 0.0224(3) Uani 1 1 d . . . . .
H54 H -0.165489 0.328265 0.385056 0.027 Uiso 1 1 calc R U . . .
C55 C -0.31312(14) 0.46758(13) 0.45519(11) 0.0251(3) Uani 1 1 d . . . . .
H55 H -0.354962 0.427185 0.509314 0.030 Uiso 1 1 calc R U . . .
C56 C -0.36473(13) 0.58530(13) 0.44938(11) 0.0250(3) Uani 1 1 d . . . . .
H56 H -0.441990 0.623549 0.499424 0.030 Uiso 1 1 calc R U . . .
C57 C -0.30593(13) 0.64812(12) 0.37214(11) 0.0218(3) Uani 1 1 d . . . . .
H57 H -0.342062 0.728168 0.368421 0.026 Uiso 1 1 calc R U . . .
C58 C -0.19268(12) 0.58993(11) 0.30067(10) 0.0178(3) Uani 1 1 d . . . . .
C59 C -0.10628(12) 0.63456(11) 0.21175(10) 0.0195(3) Uani 1 1 d . . . . .
H59A H -0.147840 0.663815 0.162295 0.023 Uiso 1 1 calc R U . . .
H59B H -0.076635 0.697108 0.232999 0.023 Uiso 1 1 calc R U . . .
N60 N -0.00259(10) 0.53031(9) 0.17026(8) 0.0172(2) Uani 1 1 d . . . . .
C61 C 0.10618(12) 0.53351(11) 0.08720(10) 0.0170(2) Uani 1 1 d . . . . .
C62 C 0.09635(13) 0.58828(11) 0.00121(10) 0.0198(3) Uani 1 1 d . . . . .
H62 H 0.015501 0.620652 -0.003014 0.024 Uiso 1 1 calc R U . . .
C63 C 0.20265(13) 0.59670(12) -0.07898(10) 0.0213(3) Uani 1 1 d . . . . .
H63 H 0.194237 0.635316 -0.136828 0.026 Uiso 1 1 calc R U . . .
C64 C 0.32097(13) 0.54806(12) -0.07344(10) 0.0206(3) Uani 1 1 d . . . . .
O65 O 0.43176(10) 0.55253(9) -0.14656(7) 0.0270(2) Uani 1 1 d . . . . .
C66 C 0.42417(17) 0.60433(17) -0.23727(12) 0.0381(4) Uani 1 1 d . . . . .
H66A H 0.381291 0.563142 -0.267694 0.057 Uiso 1 1 calc R U . . .
H66B H 0.509065 0.599374 -0.284550 0.057 Uiso 1 1 calc R U . . .
H66C H 0.376964 0.685991 -0.221786 0.057 Uiso 1 1 calc R U . . .
C67 C 0.33313(13) 0.49245(12) 0.01212(10) 0.0204(3) Uani 1 1 d . . . . .
H67 H 0.414038 0.458674 0.015732 0.024 Uiso 1 1 calc R U . . .
C68 C 0.22669(12) 0.48697(11) 0.09134(10) 0.0176(3) Uani 1 1 d . . . . .
O69 O 0.23301(9) 0.44493(8) 0.18314(7) 0.01904(19) Uani 1 1 d . . . . .
C70 C 0.30149(12) 0.33370(11) 0.18397(10) 0.0183(3) Uani 1 1 d . . . . .
O71 O 0.37106(10) 0.27496(9) 0.10902(8) 0.0265(2) Uani 1 1 d . . . . .
C72 C 0.27751(13) 0.29564(12) 0.28833(10) 0.0200(3) Uani 1 1 d . . . . .
C73 C 0.17106(14) 0.35123(13) 0.36867(11) 0.0246(3) Uani 1 1 d . . . . .
H73 H 0.115924 0.420641 0.359363 0.030 Uiso 1 1 calc R U . . .
C74 C 0.14619(15) 0.30455(15) 0.46228(11) 0.0307(3) Uani 1 1 d . . . . .
H74 H 0.072865 0.341317 0.516752 0.037 Uiso 1 1 calc R U . . .
C75 C 0.22777(16) 0.20452(15) 0.47672(12) 0.0314(3) Uani 1 1 d . . . . .
H75 H 0.209697 0.172691 0.540842 0.038 Uiso 1 1 calc R U . . .
C76 C 0.33568(15) 0.15078(14) 0.39789(12) 0.0294(3) Uani 1 1 d . . . . .
H76 H 0.392557 0.083510 0.408495 0.035 Uiso 1 1 calc R U . . .
C77 C 0.36044(14) 0.19552(12) 0.30334(11) 0.0239(3) Uani 1 1 d . . . . .
H77 H 0.433604 0.158155 0.248984 0.029 Uiso 1 1 calc R U . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.2286(16) . ?
C2 N10 1.3723(16) . ?
C2 C3 1.4824(18) . ?
C3 C8 1.3900(18) . ?
C3 C4 1.3916(18) . ?
C4 C5 1.392(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.3904(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.3880(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.5002(18) . ?
C9 N10 1.4708(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N10 C11 1.4186(16) . ?
C11 C12 1.3877(18) . ?
C11 C18 1.4012(18) . ?
C12 C13 1.3931(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.3882(19) . ?
C13 H13 0.9500 . ?
C14 O15 1.3664(16) . ?
C14 C17 1.3953(19) . ?
O15 C16 1.4261(18) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.3789(18) . ?
C17 H17 0.9500 . ?
C18 O19 1.3989(15) . ?
O19 C20 1.3695(15) . ?
C20 O21 1.2012(16) . ?
C20 C22 1.4854(18) . ?
C22 C23 1.3942(19) . ?
C22 C27 1.3966(19) . ?
C23 C24 1.387(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.389(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.381(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.388(2) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
O51 C52 1.2276(16) . ?
C52 N60 1.3727(16) . ?
C52 C53 1.4817(18) . ?
C53 C54 1.3905(18) . ?
C53 C58 1.3909(18) . ?
C54 C55 1.392(2) . ?
C54 H54 0.9500 . ?
C55 C56 1.394(2) . ?
C55 H55 0.9500 . ?
C56 C57 1.391(2) . ?
C56 H56 0.9500 . ?
C57 C58 1.3879(19) . ?
C57 H57 0.9500 . ?
C58 C59 1.5034(18) . ?
C59 N60 1.4698(16) . ?
C59 H59A 0.9900 . ?
C59 H59B 0.9900 . ?
N60 C61 1.4178(16) . ?
C61 C62 1.3903(18) . ?
C61 C68 1.4013(18) . ?
C62 C63 1.3944(19) . ?
C62 H62 0.9500 . ?
C63 C64 1.389(2) . ?
C63 H63 0.9500 . ?
C64 O65 1.3699(16) . ?
C64 C67 1.3965(19) . ?
O65 C66 1.4289(19) . ?
C66 H66A 0.9800 . ?
C66 H66B 0.9800 . ?
C66 H66C 0.9800 . ?
C67 C68 1.3793(18) . ?
C67 H67 0.9500 . ?
C68 O69 1.3976(15) . ?
O69 C70 1.3687(16) . ?
C70 O71 1.2015(17) . ?
C70 C72 1.4863(18) . ?
C72 C73 1.395(2) . ?
C72 C77 1.3990(19) . ?
C73 C74 1.388(2) . ?
C73 H73 0.9500 . ?
C74 C75 1.387(2) . ?
C74 H74 0.9500 . ?
C75 C76 1.387(2) . ?
C75 H75 0.9500 . ?
C76 C77 1.390(2) . ?
C76 H76 0.9500 . ?
C77 H77 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C2 N10 125.58(12) . . ?
O1 C2 C3 128.40(12) . . ?
N10 C2 C3 106.01(10) . . ?
C8 C3 C4 121.89(12) . . ?
C8 C3 C2 108.76(11) . . ?
C4 C3 C2 129.34(12) . . ?
C3 C4 C5 117.62(12) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
C4 C5 C6 120.63(13) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 121.30(13) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C8 C7 C6 118.25(12) . . ?
C8 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
C7 C8 C3 120.29(12) . . ?
C7 C8 C9 130.04(12) . . ?
C3 C8 C9 109.67(11) . . ?
N10 C9 C8 102.12(10) . . ?
N10 C9 H9A 111.3 . . ?
C8 C9 H9A 111.3 . . ?
N10 C9 H9B 111.3 . . ?
C8 C9 H9B 111.3 . . ?
H9A C9 H9B 109.2 . . ?
C2 N10 C11 124.81(11) . . ?
C2 N10 C9 113.06(10) . . ?
C11 N10 C9 121.98(10) . . ?
C12 C11 C18 118.06(12) . . ?
C12 C11 N10 120.90(12) . . ?
C18 C11 N10 120.99(11) . . ?
C11 C12 C13 121.39(12) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C12 119.22(12) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
O15 C14 C13 124.41(12) . . ?
O15 C14 C17 115.08(12) . . ?
C13 C14 C17 120.48(12) . . ?
C14 O15 C16 117.77(11) . . ?
O15 C16 H16A 109.5 . . ?
O15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C14 119.24(12) . . ?
C18 C17 H17 120.4 . . ?
C14 C17 H17 120.4 . . ?
C17 C18 O19 121.95(12) . . ?
C17 C18 C11 121.54(12) . . ?
O19 C18 C11 116.25(11) . . ?
C20 O19 C18 118.91(10) . . ?
O21 C20 O19 123.57(12) . . ?
O21 C20 C22 125.10(12) . . ?
O19 C20 C22 111.32(11) . . ?
C23 C22 C27 119.91(13) . . ?
C23 C22 C20 117.74(12) . . ?
C27 C22 C20 122.12(12) . . ?
C24 C23 C22 119.83(13) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 120.02(14) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C26 C25 C24 120.27(14) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C27 120.25(14) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C26 C27 C22 119.68(14) . . ?
C26 C27 H27 120.2 . . ?
C22 C27 H27 120.2 . . ?
O51 C52 N60 125.82(12) . . ?
O51 C52 C53 128.31(12) . . ?
N60 C52 C53 105.86(11) . . ?
C54 C53 C58 121.86(12) . . ?
C54 C53 C52 129.10(12) . . ?
C58 C53 C52 109.04(11) . . ?
C53 C54 C55 117.55(13) . . ?
C53 C54 H54 121.2 . . ?
C55 C54 H54 121.2 . . ?
C54 C55 C56 120.56(13) . . ?
C54 C55 H55 119.7 . . ?
C56 C55 H55 119.7 . . ?
C57 C56 C55 121.64(13) . . ?
C57 C56 H56 119.2 . . ?
C55 C56 H56 119.2 . . ?
C58 C57 C56 117.76(13) . . ?
C58 C57 H57 121.1 . . ?
C56 C57 H57 121.1 . . ?
C57 C58 C53 120.61(12) . . ?
C57 C58 C59 129.97(12) . . ?
C53 C58 C59 109.42(11) . . ?
N60 C59 C58 102.13(10) . . ?
N60 C59 H59A 111.3 . . ?
C58 C59 H59A 111.3 . . ?
N60 C59 H59B 111.3 . . ?
C58 C59 H59B 111.3 . . ?
H59A C59 H59B 109.2 . . ?
C52 N60 C61 124.78(11) . . ?
C52 N60 C59 113.28(11) . . ?
C61 N60 C59 121.93(10) . . ?
C62 C61 C68 117.97(12) . . ?
C62 C61 N60 120.92(12) . . ?
C68 C61 N60 121.03(12) . . ?
C61 C62 C63 121.40(13) . . ?
C61 C62 H62 119.3 . . ?
C63 C62 H62 119.3 . . ?
C64 C63 C62 119.35(13) . . ?
C64 C63 H63 120.3 . . ?
C62 C63 H63 120.3 . . ?
O65 C64 C63 124.58(13) . . ?
O65 C64 C67 115.15(12) . . ?
C63 C64 C67 120.25(12) . . ?
C64 O65 C66 117.09(12) . . ?
O65 C66 H66A 109.5 . . ?
O65 C66 H66B 109.5 . . ?
H66A C66 H66B 109.5 . . ?
O65 C66 H66C 109.5 . . ?
H66A C66 H66C 109.5 . . ?
H66B C66 H66C 109.5 . . ?
C68 C67 C64 119.44(13) . . ?
C68 C67 H67 120.3 . . ?
C64 C67 H67 120.3 . . ?
C67 C68 O69 121.66(12) . . ?
C67 C68 C61 121.57(12) . . ?
O69 C68 C61 116.49(11) . . ?
C70 O69 C68 118.80(10) . . ?
O71 C70 O69 123.56(12) . . ?
O71 C70 C72 124.96(12) . . ?
O69 C70 C72 111.48(11) . . ?
C73 C72 C77 119.89(13) . . ?
C73 C72 C70 122.04(12) . . ?
C77 C72 C70 117.89(13) . . ?
C74 C73 C72 119.63(14) . . ?
C74 C73 H73 120.2 . . ?
C72 C73 H73 120.2 . . ?
C75 C74 C73 120.38(15) . . ?
C75 C74 H74 119.8 . . ?
C73 C74 H74 119.8 . . ?
C74 C75 C76 120.24(14) . . ?
C74 C75 H75 119.9 . . ?
C76 C75 H75 119.9 . . ?
C75 C76 C77 119.90(14) . . ?
C75 C76 H76 120.0 . . ?
C77 C76 H76 120.0 . . ?
C76 C77 C72 119.92(14) . . ?
C76 C77 H77 120.0 . . ?
C72 C77 H77 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C8 173.52(13) . . . . ?
N10 C2 C3 C8 -5.11(15) . . . . ?
O1 C2 C3 C4 -6.0(2) . . . . ?
N10 C2 C3 C4 175.36(14) . . . . ?
C8 C3 C4 C5 -0.1(2) . . . . ?
C2 C3 C4 C5 179.42(14) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
C4 C5 C6 C7 0.6(2) . . . . ?
C5 C6 C7 C8 0.4(2) . . . . ?
C6 C7 C8 C3 -1.2(2) . . . . ?
C6 C7 C8 C9 178.32(13) . . . . ?
C4 C3 C8 C7 1.0(2) . . . . ?
C2 C3 C8 C7 -178.53(12) . . . . ?
C4 C3 C8 C9 -178.55(12) . . . . ?
C2 C3 C8 C9 1.88(15) . . . . ?
C7 C8 C9 N10 -177.71(13) . . . . ?
C3 C8 C9 N10 1.83(14) . . . . ?
O1 C2 N10 C11 3.5(2) . . . . ?
C3 C2 N10 C11 -177.84(11) . . . . ?
O1 C2 N10 C9 -172.14(13) . . . . ?
C3 C2 N10 C9 6.54(15) . . . . ?
C8 C9 N10 C2 -5.32(14) . . . . ?
C8 C9 N10 C11 178.92(11) . . . . ?
C2 N10 C11 C12 -130.88(14) . . . . ?
C9 N10 C11 C12 44.37(18) . . . . ?
C2 N10 C11 C18 51.73(18) . . . . ?
C9 N10 C11 C18 -133.02(13) . . . . ?
C18 C11 C12 C13 -1.56(19) . . . . ?
N10 C11 C12 C13 -179.03(12) . . . . ?
C11 C12 C13 C14 -0.78(19) . . . . ?
C12 C13 C14 O15 179.84(12) . . . . ?
C12 C13 C14 C17 1.88(19) . . . . ?
C13 C14 O15 C16 -0.3(2) . . . . ?
C17 C14 O15 C16 177.80(12) . . . . ?
O15 C14 C17 C18 -178.74(12) . . . . ?
C13 C14 C17 C18 -0.6(2) . . . . ?
C14 C17 C18 O19 172.11(12) . . . . ?
C14 C17 C18 C11 -1.8(2) . . . . ?
C12 C11 C18 C17 2.89(19) . . . . ?
N10 C11 C18 C17 -179.65(12) . . . . ?
C12 C11 C18 O19 -171.39(11) . . . . ?
N10 C11 C18 O19 6.08(17) . . . . ?
C17 C18 O19 C20 59.07(17) . . . . ?
C11 C18 O19 C20 -126.69(12) . . . . ?
C18 O19 C20 O21 -12.97(19) . . . . ?
C18 O19 C20 C22 166.44(11) . . . . ?
O21 C20 C22 C23 -12.5(2) . . . . ?
O19 C20 C22 C23 168.04(11) . . . . ?
O21 C20 C22 C27 161.86(14) . . . . ?
O19 C20 C22 C27 -17.54(18) . . . . ?
C27 C22 C23 C24 -1.3(2) . . . . ?
C20 C22 C23 C24 173.28(12) . . . . ?
C22 C23 C24 C25 -0.4(2) . . . . ?
C23 C24 C25 C26 1.2(2) . . . . ?
C24 C25 C26 C27 -0.3(2) . . . . ?
C25 C26 C27 C22 -1.3(2) . . . . ?
C23 C22 C27 C26 2.1(2) . . . . ?
C20 C22 C27 C26 -172.19(13) . . . . ?
O51 C52 C53 C54 5.9(2) . . . . ?
N60 C52 C53 C54 -175.48(13) . . . . ?
O51 C52 C53 C58 -174.31(13) . . . . ?
N60 C52 C53 C58 4.34(14) . . . . ?
C58 C53 C54 C55 0.1(2) . . . . ?
C52 C53 C54 C55 179.89(13) . . . . ?
C53 C54 C55 C56 1.0(2) . . . . ?
C54 C55 C56 C57 -0.8(2) . . . . ?
C55 C56 C57 C58 -0.5(2) . . . . ?
C56 C57 C58 C53 1.6(2) . . . . ?
C56 C57 C58 C59 -177.79(13) . . . . ?
C54 C53 C58 C57 -1.4(2) . . . . ?
C52 C53 C58 C57 178.78(12) . . . . ?
C54 C53 C58 C59 178.09(12) . . . . ?
C52 C53 C58 C59 -1.75(15) . . . . ?
C57 C58 C59 N60 178.08(13) . . . . ?
C53 C58 C59 N60 -1.33(14) . . . . ?
O51 C52 N60 C61 -6.2(2) . . . . ?
C53 C52 N60 C61 175.14(11) . . . . ?
O51 C52 N60 C59 173.29(13) . . . . ?
C53 C52 N60 C59 -5.40(14) . . . . ?
C58 C59 N60 C52 4.29(14) . . . . ?
C58 C59 N60 C61 -176.23(11) . . . . ?
C52 N60 C61 C62 132.00(14) . . . . ?
C59 N60 C61 C62 -47.41(18) . . . . ?
C52 N60 C61 C68 -51.36(18) . . . . ?
C59 N60 C61 C68 129.22(13) . . . . ?
C68 C61 C62 C63 0.21(19) . . . . ?
N60 C61 C62 C63 176.95(12) . . . . ?
C61 C62 C63 C64 0.8(2) . . . . ?
C62 C63 C64 O65 -178.86(12) . . . . ?
C62 C63 C64 C67 -0.7(2) . . . . ?
C63 C64 O65 C66 -4.3(2) . . . . ?
C67 C64 O65 C66 177.44(13) . . . . ?
O65 C64 C67 C68 177.85(12) . . . . ?
C63 C64 C67 C68 -0.5(2) . . . . ?
C64 C67 C68 O69 -172.19(12) . . . . ?
C64 C67 C68 C61 1.6(2) . . . . ?
C62 C61 C68 C67 -1.43(19) . . . . ?
N60 C61 C68 C67 -178.16(12) . . . . ?
C62 C61 C68 O69 172.63(11) . . . . ?
N60 C61 C68 O69 -4.10(18) . . . . ?
C67 C68 O69 C70 -59.52(16) . . . . ?
C61 C68 O69 C70 126.42(12) . . . . ?
C68 O69 C70 O71 10.84(19) . . . . ?
C68 O69 C70 C72 -168.57(11) . . . . ?
O71 C70 C72 C73 -160.22(14) . . . . ?
O69 C70 C72 C73 19.18(18) . . . . ?
O71 C70 C72 C77 14.9(2) . . . . ?
O69 C70 C72 C77 -165.72(12) . . . . ?
C77 C72 C73 C74 -2.0(2) . . . . ?
C70 C72 C73 C74 172.96(13) . . . . ?
C72 C73 C74 C75 1.3(2) . . . . ?
C73 C74 C75 C76 0.6(2) . . . . ?
C74 C75 C76 C77 -1.7(2) . . . . ?
C75 C76 C77 C72 1.0(2) . . . . ?
C73 C72 C77 C76 0.9(2) . . . . ?
C70 C72 C77 C76 -174.31(13) . . . . ?

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR YYC499                                                 #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
####################################################################### 
# 
# 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_YYC4111
_database_code_depnum_ccdc_archive 'CCDC 1910247'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;CNRS
France
;
_audit_update_record             
;
2019-04-15 deposited with the CCDC.	2019-07-23 downloaded from the CCDC.
;


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H14 N2 O5'
_chemical_formula_sum            'C21 H14 N2 O5'
_chemical_formula_weight         374.34
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                            UNIT CELL INFORMATION                             #
#------------------------------------------------------------------------------#


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
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                   10.9939(18)
_cell_length_b                   10.3250(19)
_cell_length_c                   15.434(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.239(6)
_cell_angle_gamma                90
_cell_volume                     1733.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    7616
_cell_measurement_theta_min      2.3809
_cell_measurement_theta_max      27.5150
_cell_measurement_wavelength     0.71073

#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             776
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.801
_exptl_absorpt_correction_T_max  0.964

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_diffrn_reflns_av_r_equivalents  0.0403
_diffrn_reflns_av_uneti/neti     0.0387
_diffrn_reflns_number            13686
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.381
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.982
_reflns_number_total             3919
_reflns_number_gt                3162
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0471P)²+0.7789P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018_3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.029(3)
_refine_ls_number_reflns         3919
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1090
_refine_ls_wR_factor_gt          0.1002
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.050

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................



# ............... End of .HKL file ........................................... #
#------------------------------------------------------------------------------#
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.39960(10) 0.52273(11) 0.27412(7) 0.0312(3) Uani 1 1 d . . . . .
C2 C 0.37108(13) 0.51786(14) 0.19481(9) 0.0240(3) Uani 1 1 d . . . . .
C3 C 0.39217(13) 0.61623(14) 0.12813(10) 0.0241(3) Uani 1 1 d . . . . .
C4 C 0.44690(14) 0.73764(16) 0.14028(11) 0.0312(4) Uani 1 1 d . . . . .
H4 H 0.475744 0.769345 0.197306 0.037 Uiso 1 1 calc R U . . .
C5 C 0.45805(14) 0.81114(16) 0.06626(12) 0.0343(4) Uani 1 1 d . . . . .
H5 H 0.494416 0.894692 0.072653 0.041 Uiso 1 1 calc R U . . .
C6 C 0.41641(14) 0.76337(17) -0.01712(11) 0.0334(4) Uani 1 1 d . . . . .
H6 H 0.423868 0.815355 -0.066876 0.040 Uiso 1 1 calc R U . . .
C7 C 0.36406(14) 0.64077(17) -0.02875(10) 0.0305(3) Uani 1 1 d . . . . .
H7 H 0.337497 0.607763 -0.085775 0.037 Uiso 1 1 calc R U . . .
C8 C 0.35158(13) 0.56778(14) 0.04514(9) 0.0238(3) Uani 1 1 d . . . . .
C9 C 0.29933(14) 0.43429(15) 0.05248(9) 0.0253(3) Uani 1 1 d . . . . .
H9A H 0.211797 0.430623 0.026205 0.030 Uiso 1 1 calc R U . . .
H9B H 0.346175 0.368835 0.024004 0.030 Uiso 1 1 calc R U . . .
N10 N 0.31375(11) 0.41498(12) 0.14803(7) 0.0231(3) Uani 1 1 d . . . . .
C11 C 0.28656(12) 0.29422(14) 0.18512(9) 0.0213(3) Uani 1 1 d . . . . .
C12 C 0.31884(13) 0.17828(15) 0.14756(10) 0.0270(3) Uani 1 1 d . . . . .
H12 H 0.358899 0.180712 0.096984 0.032 Uiso 1 1 calc R U . . .
C13 C 0.29332(15) 0.06040(15) 0.18295(10) 0.0306(4) Uani 1 1 d . . . . .
H13 H 0.315713 -0.017586 0.156635 0.037 Uiso 1 1 calc R U . . .
C14 C 0.23508(15) 0.05545(16) 0.25681(10) 0.0307(4) Uani 1 1 d . . . . .
H14 H 0.218632 -0.025853 0.281514 0.037 Uiso 1 1 calc R U . . .
C15 C 0.20079(14) 0.16916(15) 0.29469(10) 0.0281(3) Uani 1 1 d . . . . .
H15 H 0.160466 0.166030 0.345123 0.034 Uiso 1 1 calc R U . . .
C16 C 0.22575(13) 0.28725(14) 0.25847(9) 0.0219(3) Uani 1 1 d . . . . .
O17 O 0.17811(9) 0.40352(10) 0.28630(6) 0.0231(2) Uani 1 1 d . . . . .
C18 C 0.19231(13) 0.43342(14) 0.37286(9) 0.0236(3) Uani 1 1 d . . . . .
O19 O 0.23916(12) 0.36418(12) 0.43053(7) 0.0386(3) Uani 1 1 d . . . . .
C20 C 0.14016(12) 0.56377(14) 0.38631(8) 0.0205(3) Uani 1 1 d . . . . .
C21 C 0.10746(13) 0.65073(15) 0.31781(9) 0.0235(3) Uani 1 1 d . . . . .
H21 H 0.116584 0.626601 0.259699 0.028 Uiso 1 1 calc R U . . .
C22 C 0.06172(13) 0.77220(15) 0.33391(9) 0.0243(3) Uani 1 1 d . . . . .
H22 H 0.040048 0.830685 0.286709 0.029 Uiso 1 1 calc R U . . .
C23 C 0.04731(13) 0.80909(14) 0.41811(9) 0.0216(3) Uani 1 1 d . . . . .
H23 H 0.016293 0.892218 0.429715 0.026 Uiso 1 1 calc R U . . .
C24 C 0.07978(12) 0.72033(14) 0.48488(8) 0.0200(3) Uani 1 1 d . . . . .
C25 C 0.12547(12) 0.59841(14) 0.47157(8) 0.0201(3) Uani 1 1 d . . . . .
H25 H 0.146220 0.540030 0.518954 0.024 Uiso 1 1 calc R U . . .
N26 N 0.06667(12) 0.75908(12) 0.57453(8) 0.0256(3) Uani 1 1 d . . . . .
O27 O 0.07905(13) 0.67583(12) 0.63177(7) 0.0409(3) Uani 1 1 d . . . . .
O28 O 0.04344(12) 0.87337(11) 0.58835(7) 0.0384(3) Uani 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.2203(18) . ?
C2 N10 1.3844(18) . ?
C2 C3 1.488(2) . ?
C3 C8 1.388(2) . ?
C3 C4 1.391(2) . ?
C4 C5 1.392(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.504(2) . ?
C9 N10 1.4739(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N10 C11 1.4216(19) . ?
C11 C16 1.397(2) . ?
C11 C12 1.398(2) . ?
C12 C13 1.379(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(2) . ?
C15 H15 0.9500 . ?
C16 O17 1.4015(16) . ?
O17 C18 1.3583(16) . ?
C18 O19 1.1989(18) . ?
C18 C20 1.489(2) . ?
C20 C21 1.394(2) . ?
C20 C25 1.3953(18) . ?
C21 C22 1.387(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.385(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.3871(19) . ?
C23 H23 0.9500 . ?
C24 C25 1.382(2) . ?
C24 N26 1.4672(17) . ?
C25 H25 0.9500 . ?
N26 O27 1.2261(16) . ?
N26 O28 1.2323(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C2 N10 125.96(14) . . ?
O1 C2 C3 128.52(14) . . ?
N10 C2 C3 105.51(12) . . ?
C8 C3 C4 121.65(14) . . ?
C8 C3 C2 109.33(13) . . ?
C4 C3 C2 128.99(14) . . ?
C3 C4 C5 117.90(15) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C4 C5 C6 120.63(15) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 121.09(15) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C6 118.36(15) . . ?
C8 C7 H7 120.8 . . ?
C6 C7 H7 120.8 . . ?
C3 C8 C7 120.35(14) . . ?
C3 C8 C9 109.67(13) . . ?
C7 C8 C9 129.97(14) . . ?
N10 C9 C8 102.23(11) . . ?
N10 C9 H9A 111.3 . . ?
C8 C9 H9A 111.3 . . ?
N10 C9 H9B 111.3 . . ?
C8 C9 H9B 111.3 . . ?
H9A C9 H9B 109.2 . . ?
C2 N10 C11 124.69(12) . . ?
C2 N10 C9 113.19(12) . . ?
C11 N10 C9 121.53(11) . . ?
C16 C11 C12 118.13(13) . . ?
C16 C11 N10 121.63(12) . . ?
C12 C11 N10 120.23(12) . . ?
C13 C12 C11 120.89(14) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.16(14) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 120.05(15) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 119.56(14) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C11 121.20(13) . . ?
C15 C16 O17 121.74(12) . . ?
C11 C16 O17 116.59(12) . . ?
C18 O17 C16 120.05(11) . . ?
O19 C18 O17 124.85(13) . . ?
O19 C18 C20 124.64(13) . . ?
O17 C18 C20 110.50(11) . . ?
C21 C20 C25 119.86(13) . . ?
C21 C20 C18 122.61(12) . . ?
C25 C20 C18 117.52(12) . . ?
C22 C21 C20 120.48(13) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C23 C22 C21 120.67(13) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 117.62(13) . . ?
C22 C23 H23 121.2 . . ?
C24 C23 H23 121.2 . . ?
C25 C24 C23 123.49(12) . . ?
C25 C24 N26 118.41(12) . . ?
C23 C24 N26 118.10(12) . . ?
C24 C25 C20 117.88(12) . . ?
C24 C25 H25 121.1 . . ?
C20 C25 H25 121.1 . . ?
O27 N26 O28 123.43(12) . . ?
O27 N26 C24 118.20(12) . . ?
O28 N26 C24 118.36(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C8 176.39(15) . . . . ?
N10 C2 C3 C8 -2.13(15) . . . . ?
O1 C2 C3 C4 -1.4(3) . . . . ?
N10 C2 C3 C4 -179.94(15) . . . . ?
C8 C3 C4 C5 1.1(2) . . . . ?
C2 C3 C4 C5 178.72(14) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
C5 C6 C7 C8 1.5(2) . . . . ?
C4 C3 C8 C7 -0.5(2) . . . . ?
C2 C3 C8 C7 -178.45(13) . . . . ?
C4 C3 C8 C9 178.80(13) . . . . ?
C2 C3 C8 C9 0.80(16) . . . . ?
C6 C7 C8 C3 -0.9(2) . . . . ?
C6 C7 C8 C9 -179.94(14) . . . . ?
C3 C8 C9 N10 0.75(15) . . . . ?
C7 C8 C9 N10 179.91(14) . . . . ?
O1 C2 N10 C11 -4.6(2) . . . . ?
C3 C2 N10 C11 173.98(12) . . . . ?
O1 C2 N10 C9 -175.86(14) . . . . ?
C3 C2 N10 C9 2.71(16) . . . . ?
C8 C9 N10 C2 -2.21(15) . . . . ?
C8 C9 N10 C11 -173.79(12) . . . . ?
C2 N10 C11 C16 50.3(2) . . . . ?
C9 N10 C11 C16 -139.07(14) . . . . ?
C2 N10 C11 C12 -130.69(15) . . . . ?
C9 N10 C11 C12 39.89(19) . . . . ?
C16 C11 C12 C13 -1.2(2) . . . . ?
N10 C11 C12 C13 179.84(13) . . . . ?
C11 C12 C13 C14 -0.1(2) . . . . ?
C12 C13 C14 C15 0.9(2) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C14 C15 C16 C11 -1.0(2) . . . . ?
C14 C15 C16 O17 170.83(13) . . . . ?
C12 C11 C16 C15 1.7(2) . . . . ?
N10 C11 C16 C15 -179.32(13) . . . . ?
C12 C11 C16 O17 -170.50(12) . . . . ?
N10 C11 C16 O17 8.48(19) . . . . ?
C15 C16 O17 C18 51.44(18) . . . . ?
C11 C16 O17 C18 -136.40(14) . . . . ?
C16 O17 C18 O19 -3.5(2) . . . . ?
C16 O17 C18 C20 177.14(11) . . . . ?
O19 C18 C20 C21 167.75(16) . . . . ?
O17 C18 C20 C21 -12.92(19) . . . . ?
O19 C18 C20 C25 -11.6(2) . . . . ?
O17 C18 C20 C25 167.72(12) . . . . ?
C25 C20 C21 C22 0.8(2) . . . . ?
C18 C20 C21 C22 -178.59(13) . . . . ?
C20 C21 C22 C23 -0.2(2) . . . . ?
C21 C22 C23 C24 -0.2(2) . . . . ?
C22 C23 C24 C25 0.1(2) . . . . ?
C22 C23 C24 N26 179.09(12) . . . . ?
C23 C24 C25 C20 0.4(2) . . . . ?
N26 C24 C25 C20 -178.56(12) . . . . ?
C21 C20 C25 C24 -0.8(2) . . . . ?
C18 C20 C25 C24 178.55(12) . . . . ?
C25 C24 N26 O27 -10.8(2) . . . . ?
C23 C24 N26 O27 170.21(14) . . . . ?
C25 C24 N26 O28 169.46(13) . . . . ?
C23 C24 N26 O28 -9.6(2) . . . . ?

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR YYC4111                                                #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
####################################################################### 
# 
# 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_YYC4132
_database_code_depnum_ccdc_archive 'CCDC 1910248'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;CNRS
France
;
_audit_update_record             
;
2019-04-15 deposited with the CCDC.	2019-07-23 downloaded from the CCDC.
;


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C25 H17 N O3'
_chemical_formula_sum            'C25 H17 N O3'
_chemical_formula_weight         379.39
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                            UNIT CELL INFORMATION                             #
#------------------------------------------------------------------------------#


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
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                   13.455(2)
_cell_length_b                   10.3927(13)
_cell_length_c                   13.4329(19)
_cell_angle_alpha                90
_cell_angle_beta                 95.302(6)
_cell_angle_gamma                90
_cell_volume                     1870.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    9244
_cell_measurement_theta_min      2.2488
_cell_measurement_theta_max      27.5370
_cell_measurement_wavelength     0.71073

#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.170
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             792
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.829
_exptl_absorpt_correction_T_max  0.985

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_diffrn_reflns_av_r_equivalents  0.0398
_diffrn_reflns_av_uneti/neti     0.0397
_diffrn_reflns_number            15362
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.050
_diffrn_reflns_theta_max         27.540
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.985
_reflns_number_total             4248
_reflns_number_gt                3530
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0451P)²+0.7202P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018_3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0179(17)
_refine_ls_number_reflns         4248
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1042
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.060

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................



# ............... End of .HKL file ........................................... #
#------------------------------------------------------------------------------#
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.37691(7) 0.25396(9) 0.84369(8) 0.0233(2) Uani 1 1 d . . . . .
C2 C 0.46720(9) 0.26885(11) 0.84659(9) 0.0166(3) Uani 1 1 d . . . . .
C3 C 0.54685(9) 0.17146(12) 0.86504(9) 0.0168(3) Uani 1 1 d . . . . .
C4 C 0.53730(10) 0.04054(13) 0.88256(10) 0.0230(3) Uani 1 1 d . . . . .
H4 H 0.473521 0.001379 0.882721 0.028 Uiso 1 1 calc R U . . .
C5 C 0.62442(11) -0.03116(13) 0.89986(12) 0.0294(3) Uani 1 1 d . . . . .
H5 H 0.620447 -0.120837 0.912597 0.035 Uiso 1 1 calc R U . . .
C6 C 0.71748(11) 0.02727(14) 0.89870(11) 0.0288(3) Uani 1 1 d . . . . .
H6 H 0.776158 -0.023282 0.910945 0.035 Uiso 1 1 calc R U . . .
C7 C 0.72614(10) 0.15855(13) 0.87989(11) 0.0243(3) Uani 1 1 d . . . . .
H7 H 0.789777 0.197721 0.878336 0.029 Uiso 1 1 calc R U . . .
C8 C 0.63948(10) 0.23019(12) 0.86356(9) 0.0180(3) Uani 1 1 d . . . . .
C9 C 0.62493(9) 0.37185(12) 0.84380(11) 0.0206(3) Uani 1 1 d . . . . .
H9A H 0.655536 0.424170 0.900121 0.025 Uiso 1 1 calc R U . . .
H9B H 0.653314 0.398061 0.781472 0.025 Uiso 1 1 calc R U . . .
N10 N 0.51569(8) 0.38347(10) 0.83419(8) 0.0176(2) Uani 1 1 d . . . . .
C11 C 0.46454(9) 0.50179(11) 0.81641(9) 0.0173(3) Uani 1 1 d . . . . .
C12 C 0.47677(10) 0.60285(12) 0.88436(10) 0.0219(3) Uani 1 1 d . . . . .
H12 H 0.523385 0.595327 0.941647 0.026 Uiso 1 1 calc R U . . .
C13 C 0.42094(11) 0.71491(12) 0.86866(11) 0.0246(3) Uani 1 1 d . . . . .
H13 H 0.429378 0.783505 0.915421 0.030 Uiso 1 1 calc R U . . .
C14 C 0.35305(11) 0.72683(12) 0.78508(11) 0.0246(3) Uani 1 1 d . . . . .
H14 H 0.314420 0.803046 0.775144 0.030 Uiso 1 1 calc R U . . .
C15 C 0.34144(10) 0.62754(13) 0.71584(10) 0.0221(3) Uani 1 1 d . . . . .
H15 H 0.295210 0.635437 0.658289 0.026 Uiso 1 1 calc R U . . .
C16 C 0.39789(9) 0.51706(12) 0.73159(9) 0.0171(3) Uani 1 1 d . . . . .
O17 O 0.38159(6) 0.41635(9) 0.66309(7) 0.0194(2) Uani 1 1 d . . . . .
C18 C 0.45919(9) 0.38257(12) 0.60955(9) 0.0173(3) Uani 1 1 d . . . . .
O19 O 0.53559(7) 0.44263(9) 0.61087(7) 0.0237(2) Uani 1 1 d . . . . .
C20 C 0.43451(9) 0.26478(12) 0.54966(9) 0.0164(3) Uani 1 1 d . . . . .
C21 C 0.48180(9) 0.24656(12) 0.46102(9) 0.0176(3) Uani 1 1 d . . . . .
H21 H 0.529450 0.307286 0.442299 0.021 Uiso 1 1 calc R U . . .
C22 C 0.45880(9) 0.14141(12) 0.40238(10) 0.0181(3) Uani 1 1 d . . . . .
H22 H 0.489192 0.130961 0.341815 0.022 Uiso 1 1 calc R U . . .
C23 C 0.39004(9) 0.04739(12) 0.43069(9) 0.0164(3) Uani 1 1 d . . . . .
C24 C 0.36447(10) -0.06217(12) 0.37108(10) 0.0203(3) Uani 1 1 d . . . . .
H24 H 0.392406 -0.072967 0.309198 0.024 Uiso 1 1 calc R U . . .
C25 C 0.29995(10) -0.15265(12) 0.40165(10) 0.0224(3) Uani 1 1 d . . . . .
H25 H 0.283294 -0.225396 0.360637 0.027 Uiso 1 1 calc R U . . .
C26 C 0.25801(10) -0.13899(12) 0.49330(10) 0.0209(3) Uani 1 1 d . . . . .
H26 H 0.214415 -0.203282 0.514504 0.025 Uiso 1 1 calc R U . . .
C27 C 0.28004(9) -0.03289(12) 0.55200(10) 0.0183(3) Uani 1 1 d . . . . .
H27 H 0.250832 -0.023764 0.613345 0.022 Uiso 1 1 calc R U . . .
C28 C 0.34583(9) 0.06320(12) 0.52223(9) 0.0160(3) Uani 1 1 d . . . . .
C29 C 0.36853(9) 0.17509(12) 0.57993(9) 0.0167(3) Uani 1 1 d . . . . .
H29 H 0.337924 0.188307 0.640073 0.020 Uiso 1 1 calc R U . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.2217(15) . ?
C2 N10 1.3756(16) . ?
C2 C3 1.4783(17) . ?
C3 C4 1.3887(18) . ?
C3 C8 1.3896(18) . ?
C4 C5 1.390(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.3838(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.5055(17) . ?
C9 N10 1.4686(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N10 C11 1.4185(16) . ?
C11 C12 1.3913(17) . ?
C11 C16 1.3923(18) . ?
C12 C13 1.3913(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.3883(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.3822(18) . ?
C15 H15 0.9500 . ?
C16 O17 1.3975(15) . ?
O17 C18 1.3674(15) . ?
C18 O19 1.2013(15) . ?
C18 C20 1.4855(17) . ?
C20 C29 1.3745(17) . ?
C20 C21 1.4136(17) . ?
C21 C22 1.3658(18) . ?
C21 H21 0.9500 . ?
C22 C23 1.4213(17) . ?
C22 H22 0.9500 . ?
C23 C24 1.4161(18) . ?
C23 C28 1.4240(17) . ?
C24 C25 1.3683(19) . ?
C24 H24 0.9500 . ?
C25 C26 1.4081(19) . ?
C25 H25 0.9500 . ?
C26 C27 1.3719(18) . ?
C26 H26 0.9500 . ?
C27 C28 1.4163(17) . ?
C27 H27 0.9500 . ?
C28 C29 1.4151(17) . ?
C29 H29 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C2 N10 125.96(11) . . ?
O1 C2 C3 128.45(11) . . ?
N10 C2 C3 105.58(10) . . ?
C4 C3 C8 122.00(12) . . ?
C4 C3 C2 128.48(12) . . ?
C8 C3 C2 109.52(11) . . ?
C3 C4 C5 117.63(13) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
C4 C5 C6 120.62(13) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C7 121.26(13) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 118.15(13) . . ?
C8 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
C7 C8 C3 120.34(12) . . ?
C7 C8 C9 130.39(12) . . ?
C3 C8 C9 109.26(11) . . ?
N10 C9 C8 102.04(10) . . ?
N10 C9 H9A 111.4 . . ?
C8 C9 H9A 111.4 . . ?
N10 C9 H9B 111.4 . . ?
C8 C9 H9B 111.4 . . ?
H9A C9 H9B 109.2 . . ?
C2 N10 C11 122.88(10) . . ?
C2 N10 C9 113.59(10) . . ?
C11 N10 C9 123.51(10) . . ?
C12 C11 C16 118.62(11) . . ?
C12 C11 N10 121.19(11) . . ?
C16 C11 N10 120.15(11) . . ?
C11 C12 C13 120.20(13) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 120.25(12) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.08(12) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 119.26(12) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C11 121.55(12) . . ?
C15 C16 O17 118.08(11) . . ?
C11 C16 O17 120.23(11) . . ?
C18 O17 C16 117.23(10) . . ?
O19 C18 O17 123.56(12) . . ?
O19 C18 C20 125.76(12) . . ?
O17 C18 C20 110.68(10) . . ?
C29 C20 C21 120.78(11) . . ?
C29 C20 C18 121.12(11) . . ?
C21 C20 C18 118.10(11) . . ?
C22 C21 C20 119.82(12) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C23 120.94(12) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C24 C23 C22 122.11(12) . . ?
C24 C23 C28 118.82(11) . . ?
C22 C23 C28 119.07(11) . . ?
C25 C24 C23 120.70(12) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C26 120.65(12) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C27 C26 C25 120.05(12) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C28 120.79(12) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C29 C28 C27 122.25(12) . . ?
C29 C28 C23 118.78(11) . . ?
C27 C28 C23 118.97(11) . . ?
C20 C29 C28 120.52(12) . . ?
C20 C29 H29 119.7 . . ?
C28 C29 H29 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
O1 C2 C3 C4 0.5(2) . . . . ?
N10 C2 C3 C4 179.75(13) . . . . ?
O1 C2 C3 C8 -178.96(13) . . . . ?
N10 C2 C3 C8 0.25(14) . . . . ?
C8 C3 C4 C5 0.6(2) . . . . ?
C2 C3 C4 C5 -178.81(13) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C4 C5 C6 C7 -0.2(2) . . . . ?
C5 C6 C7 C8 0.8(2) . . . . ?
C6 C7 C8 C3 -0.7(2) . . . . ?
C6 C7 C8 C9 178.61(13) . . . . ?
C4 C3 C8 C7 -0.1(2) . . . . ?
C2 C3 C8 C7 179.48(12) . . . . ?
C4 C3 C8 C9 -179.47(12) . . . . ?
C2 C3 C8 C9 0.07(14) . . . . ?
C7 C8 C9 N10 -179.66(13) . . . . ?
C3 C8 C9 N10 -0.33(14) . . . . ?
O1 C2 N10 C11 0.3(2) . . . . ?
C3 C2 N10 C11 -178.95(11) . . . . ?
O1 C2 N10 C9 178.74(12) . . . . ?
C3 C2 N10 C9 -0.49(14) . . . . ?
C8 C9 N10 C2 0.51(14) . . . . ?
C8 C9 N10 C11 178.97(11) . . . . ?
C2 N10 C11 C12 116.61(14) . . . . ?
C9 N10 C11 C12 -61.70(18) . . . . ?
C2 N10 C11 C16 -61.02(17) . . . . ?
C9 N10 C11 C16 120.66(13) . . . . ?
C16 C11 C12 C13 1.92(19) . . . . ?
N10 C11 C12 C13 -175.75(12) . . . . ?
C11 C12 C13 C14 -0.2(2) . . . . ?
C12 C13 C14 C15 -0.9(2) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
C14 C15 C16 C11 1.46(19) . . . . ?
C14 C15 C16 O17 177.22(11) . . . . ?
C12 C11 C16 C15 -2.55(19) . . . . ?
N10 C11 C16 C15 175.15(12) . . . . ?
C12 C11 C16 O17 -178.22(11) . . . . ?
N10 C11 C16 O17 -0.52(18) . . . . ?
C15 C16 O17 C18 116.74(13) . . . . ?
C11 C16 O17 C18 -67.45(15) . . . . ?
C16 O17 C18 O19 -7.93(18) . . . . ?
C16 O17 C18 C20 173.09(10) . . . . ?
O19 C18 C20 C29 153.40(13) . . . . ?
O17 C18 C20 C29 -27.65(16) . . . . ?
O19 C18 C20 C21 -25.83(19) . . . . ?
O17 C18 C20 C21 153.13(11) . . . . ?
C29 C20 C21 C22 2.73(18) . . . . ?
C18 C20 C21 C22 -178.04(11) . . . . ?
C20 C21 C22 C23 -1.98(18) . . . . ?
C21 C22 C23 C24 179.67(12) . . . . ?
C21 C22 C23 C28 -0.75(18) . . . . ?
C22 C23 C24 C25 178.32(12) . . . . ?
C28 C23 C24 C25 -1.26(19) . . . . ?
C23 C24 C25 C26 -0.3(2) . . . . ?
C24 C25 C26 C27 1.4(2) . . . . ?
C25 C26 C27 C28 -0.78(19) . . . . ?
C26 C27 C28 C29 178.65(12) . . . . ?
C26 C27 C28 C23 -0.79(18) . . . . ?
C24 C23 C28 C29 -177.67(11) . . . . ?
C22 C23 C28 C29 2.74(17) . . . . ?
C24 C23 C28 C27 1.79(17) . . . . ?
C22 C23 C28 C27 -177.79(11) . . . . ?
C21 C20 C29 C28 -0.69(18) . . . . ?
C18 C20 C29 C28 -179.89(11) . . . . ?
C27 C28 C29 C20 178.52(11) . . . . ?
C23 C28 C29 C20 -2.03(18) . . . . ?


#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR YYC4132                                                #
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#                                                                              #
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