# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# 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_YYC438
_database_code_depnum_ccdc_archive 'CCDC 1895843'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;Univ Rennes, CNRS, ISCR - UMR6226, F-35000 Rennes
France
;
_audit_update_record             
;
2019-02-06 deposited with the CCDC.	2019-08-02 downloaded from the CCDC.
;

_audit_creation_date             2018-11-19
_audit_creation_method           'SHELXL-2018_3, CRYSCALC (Oct. 2018)'
_audit_contact_author_adress     
;
     Centre de Diffractom\'etrie X
     UMR6226 CNRS Universit\'e de Rennes 1
     Institut des Sciences Chimiques de Rennes
     Campus de Beaulieu
     Avenue du G\'en\'eral Leclerc
     35042 RENNES Cedex France
;

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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H15 N O2'
_chemical_formula_sum            'C18 H15 N O2'
_chemical_formula_weight         277.31
_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                   6.1964(7)
_cell_length_b                   8.1764(8)
_cell_length_c                   14.4347(16)
_cell_angle_alpha                94.139(4)
_cell_angle_beta                 93.272(4)
_cell_angle_gamma                107.361(3)
_cell_volume                     693.81(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    8713
_cell_measurement_theta_min      2.8393
_cell_measurement_theta_max      27.5125
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             292
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.087
_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  0.787
_exptl_absorpt_correction_T_max  0.980

#------------------------------------------------------------------------------#
#                               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  0.0501
_diffrn_reflns_av_uneti/neti     0.0456
_diffrn_reflns_number            13067
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.839
_diffrn_reflns_theta_max         27.551
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_reflns_number_total             3176
_reflns_number_gt                2737
_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, 2018)'

#------------------------------------------------------------------------------#
#                            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)+(0.0783P)²+0.2903P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3176
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1412
_refine_ls_wR_factor_gt          0.1333
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.327
_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 0.76996(17) 0.27924(13) 0.13618(7) 0.0246(3) Uani 1 1 d . . . . .
C2 C 0.6505(2) 0.37251(16) 0.14967(9) 0.0168(3) Uani 1 1 d . . . . .
C3 C 0.6712(2) 0.54115(16) 0.11375(9) 0.0162(3) Uani 1 1 d . . . . .
C4 C 0.8334(2) 0.63339(18) 0.05899(10) 0.0223(3) Uani 1 1 d . . . . .
H4 H 0.952360 0.591052 0.039766 0.027 Uiso 1 1 calc R U . . .
C5 C 0.8158(3) 0.78955(18) 0.03327(10) 0.0250(3) Uani 1 1 d . . . . .
H5 H 0.922569 0.854479 -0.005173 0.030 Uiso 1 1 calc R U . . .
C6 C 0.6431(3) 0.85199(18) 0.06326(10) 0.0251(3) Uani 1 1 d . . . . .
H6 H 0.635577 0.960083 0.045774 0.030 Uiso 1 1 calc R U . . .
C7 C 0.4811(2) 0.75895(18) 0.11846(10) 0.0223(3) Uani 1 1 d . . . . .
H7 H 0.363696 0.802094 0.138809 0.027 Uiso 1 1 calc R U . . .
C8 C 0.4966(2) 0.60106(17) 0.14281(9) 0.0172(3) Uani 1 1 d . . . . .
C9 C 0.3488(2) 0.47266(17) 0.19987(9) 0.0200(3) Uani 1 1 d . . . . .
H9A H 0.341764 0.524966 0.263217 0.024 Uiso 1 1 calc R U . . .
H9B H 0.193042 0.424041 0.169435 0.024 Uiso 1 1 calc R U . . .
N10 N 0.46664(18) 0.34073(14) 0.20275(8) 0.0172(3) Uani 1 1 d . . . . .
C11 C 0.3806(2) 0.18632(17) 0.24630(9) 0.0180(3) Uani 1 1 d . . . . .
C12 C 0.1565(2) 0.08517(18) 0.22332(9) 0.0208(3) Uani 1 1 d . . . . .
H12 H 0.062026 0.122063 0.180764 0.025 Uiso 1 1 calc R U . . .
C13 C 0.0707(2) -0.06926(18) 0.26231(10) 0.0231(3) Uani 1 1 d . . . . .
H13 H -0.082767 -0.136744 0.247230 0.028 Uiso 1 1 calc R U . . .
C14 C 0.2097(3) -0.12493(18) 0.32339(10) 0.0251(3) Uani 1 1 d . . . . .
H14 H 0.153805 -0.233069 0.347835 0.030 Uiso 1 1 calc R U . . .
C15 C 0.4303(3) -0.02181(19) 0.34845(10) 0.0258(3) Uani 1 1 d . . . . .
H15 H 0.523178 -0.059893 0.391149 0.031 Uiso 1 1 calc R U . . .
C16 C 0.5200(2) 0.13700(17) 0.31256(9) 0.0202(3) Uani 1 1 d . . . . .
C17 C 0.7462(3) 0.25352(19) 0.34625(10) 0.0241(3) Uani 1 1 d . . . . .
H17 H 0.800003 0.357781 0.317834 0.029 Uiso 1 1 calc R U . . .
C18 C 0.8832(2) 0.22246(19) 0.41498(10) 0.0249(3) Uani 1 1 d . . . . .
H18 H 0.835462 0.118232 0.443867 0.030 Uiso 1 1 calc R U . . .
C19 C 1.1071(2) 0.34962(18) 0.44557(9) 0.0216(3) Uani 1 1 d . . . . .
C20 C 1.2536(3) 0.2960(2) 0.51661(12) 0.0356(4) Uani 1 1 d . . . . .
H20A H 1.309458 0.206092 0.487444 0.053 Uiso 1 1 calc R U . . .
H20B H 1.164213 0.251282 0.568191 0.053 Uiso 1 1 calc R U . . .
H20C H 1.382660 0.395555 0.540460 0.053 Uiso 1 1 calc R U . . .
O21 O 1.17128(19) 0.48912(14) 0.41452(7) 0.0288(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 1.2245(16) . ?
C2 N10 1.3799(17) . ?
C2 C3 1.4805(17) . ?
C3 C8 1.3877(18) . ?
C3 C4 1.3883(18) . ?
C4 C5 1.388(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 1.3910(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.5020(18) . ?
C9 N10 1.4736(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N10 C11 1.4229(16) . ?
C11 C12 1.3941(19) . ?
C11 C16 1.4119(18) . ?
C12 C13 1.3892(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.4010(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.472(2) . ?
C17 C18 1.356(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.484(2) . ?
C18 H18 0.9500 . ?
C19 O21 1.2179(18) . ?
C19 C20 1.505(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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 126.40(12) . . ?
O1 C2 C3 128.03(12) . . ?
N10 C2 C3 105.57(11) . . ?
C8 C3 C4 121.99(12) . . ?
C8 C3 C2 109.54(11) . . ?
C4 C3 C2 128.47(12) . . ?
C5 C4 C3 117.78(13) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
C4 C5 C6 120.66(13) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C7 121.29(13) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 117.99(13) . . ?
C8 C7 H7 121.0 . . ?
C6 C7 H7 121.0 . . ?
C3 C8 C7 120.28(12) . . ?
C3 C8 C9 109.40(11) . . ?
C7 C8 C9 130.32(12) . . ?
N10 C9 C8 102.19(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 123.81(11) . . ?
C2 N10 C9 113.13(11) . . ?
C11 N10 C9 122.60(11) . . ?
C12 C11 C16 120.44(12) . . ?
C12 C11 N10 119.23(12) . . ?
C16 C11 N10 120.33(12) . . ?
C13 C12 C11 120.37(13) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.94(13) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 119.64(13) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 121.84(13) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C15 C16 C11 117.59(13) . . ?
C15 C16 C17 121.56(13) . . ?
C11 C16 C17 120.76(12) . . ?
C18 C17 C16 124.59(14) . . ?
C18 C17 H17 117.7 . . ?
C16 C17 H17 117.7 . . ?
C17 C18 C19 120.68(13) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
O21 C19 C18 122.33(13) . . ?
O21 C19 C20 121.39(13) . . ?
C18 C19 C20 116.27(13) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C8 177.85(13) . . . . ?
N10 C2 C3 C8 -2.34(14) . . . . ?
O1 C2 C3 C4 -1.9(2) . . . . ?
N10 C2 C3 C4 177.91(13) . . . . ?
C8 C3 C4 C5 -0.2(2) . . . . ?
C2 C3 C4 C5 179.49(12) . . . . ?
C3 C4 C5 C6 1.2(2) . . . . ?
C4 C5 C6 C7 -1.1(2) . . . . ?
C5 C6 C7 C8 -0.1(2) . . . . ?
C4 C3 C8 C7 -0.9(2) . . . . ?
C2 C3 C8 C7 179.33(12) . . . . ?
C4 C3 C8 C9 179.48(12) . . . . ?
C2 C3 C8 C9 -0.28(14) . . . . ?
C6 C7 C8 C3 1.03(19) . . . . ?
C6 C7 C8 C9 -179.45(13) . . . . ?
C3 C8 C9 N10 2.59(14) . . . . ?
C7 C8 C9 N10 -176.98(13) . . . . ?
O1 C2 N10 C11 -3.6(2) . . . . ?
C3 C2 N10 C11 176.57(11) . . . . ?
O1 C2 N10 C9 -176.00(13) . . . . ?
C3 C2 N10 C9 4.19(14) . . . . ?
C8 C9 N10 C2 -4.26(14) . . . . ?
C8 C9 N10 C11 -176.75(11) . . . . ?
C2 N10 C11 C12 -120.58(14) . . . . ?
C9 N10 C11 C12 51.10(18) . . . . ?
C2 N10 C11 C16 59.95(18) . . . . ?
C9 N10 C11 C16 -128.38(14) . . . . ?
C16 C11 C12 C13 -2.8(2) . . . . ?
N10 C11 C12 C13 177.69(12) . . . . ?
C11 C12 C13 C14 -1.1(2) . . . . ?
C12 C13 C14 C15 3.0(2) . . . . ?
C13 C14 C15 C16 -1.2(2) . . . . ?
C14 C15 C16 C11 -2.6(2) . . . . ?
C14 C15 C16 C17 173.94(14) . . . . ?
C12 C11 C16 C15 4.6(2) . . . . ?
N10 C11 C16 C15 -175.94(12) . . . . ?
C12 C11 C16 C17 -171.99(13) . . . . ?
N10 C11 C16 C17 7.5(2) . . . . ?
C15 C16 C17 C18 -2.0(2) . . . . ?
C11 C16 C17 C18 174.44(14) . . . . ?
C16 C17 C18 C19 -178.74(13) . . . . ?
C17 C18 C19 O21 4.1(2) . . . . ?
C17 C18 C19 C20 -175.08(15) . . . . ?

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR YYC438                                                 #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
####################################################################### 
# 
# 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_YYC448_2
_database_code_depnum_ccdc_archive 'CCDC 1895847'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;Univ Rennes, CNRS, ISCR - UMR6226, F-35000 Rennes
France
;
_audit_update_record             
;
2019-02-06 deposited with the CCDC.	2019-08-02 downloaded from the CCDC.
;


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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C25 H21 N O3'
_chemical_formula_sum            'C25 H21 N O3'
_chemical_formula_weight         383.43
_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                   8.2186(3)
_cell_length_b                   14.7157(8)
_cell_length_c                   16.7006(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.695(3)
_cell_angle_gamma                90
_cell_volume                     2015.61(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    9880
_cell_measurement_theta_min      2.7696
_cell_measurement_theta_max      27.6410
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.570
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             808
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.083
_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  0.819
_exptl_absorpt_correction_T_max  0.975

#------------------------------------------------------------------------------#
#                               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  0.0357
_diffrn_reflns_av_uneti/neti     0.0369
_diffrn_reflns_number            13781
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.026
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.977
_reflns_number_total             4522
_reflns_number_gt                3639
_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, 2018)'

#------------------------------------------------------------------------------#
#                            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)+(0.0425P)²+1.0132P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4522
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.042

#...............................................................................
# .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 0.94124(11) 0.79992(8) 0.53192(6) 0.0281(2) Uani 1 1 d . . . . .
C2 C 0.80762(16) 0.82615(10) 0.50515(8) 0.0217(3) Uani 1 1 d . . . . .
C3 C 0.64641(16) 0.80967(10) 0.53708(8) 0.0223(3) Uani 1 1 d . . . . .
C4 C 0.60920(18) 0.75757(11) 0.60262(9) 0.0296(3) Uani 1 1 d . . . . .
H4 H 0.692429 0.728377 0.635318 0.036 Uiso 1 1 calc R U . . .
C5 C 0.44627(19) 0.74949(12) 0.61888(10) 0.0338(4) Uani 1 1 d . . . . .
H5 H 0.416827 0.714438 0.663480 0.041 Uiso 1 1 calc R U . . .
C6 C 0.32568(18) 0.79253(12) 0.57011(10) 0.0336(4) Uani 1 1 d . . . . .
H6 H 0.214689 0.785807 0.581742 0.040 Uiso 1 1 calc R U . . .
C7 C 0.36427(18) 0.84505(11) 0.50486(9) 0.0301(3) Uani 1 1 d . . . . .
H7 H 0.281373 0.874448 0.472113 0.036 Uiso 1 1 calc R U . . .
C8 C 0.52735(17) 0.85340(10) 0.48880(8) 0.0238(3) Uani 1 1 d . . . . .
C9 C 0.60539(17) 0.90266(11) 0.42225(9) 0.0268(3) Uani 1 1 d . . . . .
H9A H 0.561751 0.881227 0.368921 0.032 Uiso 1 1 calc R U . . .
H9B H 0.589234 0.969150 0.425994 0.032 Uiso 1 1 calc R U . . .
N10 N 0.77798(14) 0.87810(8) 0.43719(7) 0.0229(3) Uani 1 1 d . . . . .
C11 C 0.90433(17) 0.90806(10) 0.38891(8) 0.0232(3) Uani 1 1 d . . . . .
C12 C 0.9429(2) 0.99992(11) 0.38522(9) 0.0309(3) Uani 1 1 d . . . . .
H12 H 0.881887 1.043074 0.413165 0.037 Uiso 1 1 calc R U . . .
C13 C 1.0702(2) 1.02867(11) 0.34082(10) 0.0364(4) Uani 1 1 d . . . . .
H13 H 1.094748 1.091589 0.337417 0.044 Uiso 1 1 calc R U . . .
C14 C 1.1618(2) 0.96572(12) 0.30140(9) 0.0356(4) Uani 1 1 d . . . . .
H14 H 1.250455 0.985270 0.271931 0.043 Uiso 1 1 calc R U . . .
C15 C 1.12336(19) 0.87394(11) 0.30514(9) 0.0299(3) Uani 1 1 d . . . . .
H15 H 1.186476 0.831159 0.277921 0.036 Uiso 1 1 calc R U . . .
C16 C 0.99365(17) 0.84329(10) 0.34818(8) 0.0235(3) Uani 1 1 d . . . . .
C17 C 0.95303(17) 0.74530(10) 0.35044(8) 0.0230(3) Uani 1 1 d . . . . .
C18 C 0.77546(17) 0.72179(10) 0.33666(9) 0.0252(3) Uani 1 1 d . . . . .
O19 O 0.68804(13) 0.75268(8) 0.28249(7) 0.0370(3) Uani 1 1 d . . . . .
O20A O 0.727(6) 0.663(4) 0.391(4) 0.0319(3) Uani 0.5 1 d . . P A 1
C21A C 0.565(2) 0.6252(13) 0.3660(5) 0.0431(16) Uani 0.5 1 d . . P A 1
H21A H 0.557616 0.610958 0.307902 0.052 Uiso 0.5 1 calc R U P A 1
H21B H 0.476426 0.667400 0.377962 0.052 Uiso 0.5 1 calc R U P A 1
C22A C 0.5605(8) 0.5375(5) 0.4174(3) 0.0556(11) Uani 0.5 1 d . . P A 1
H22A H 0.456914 0.505872 0.405249 0.083 Uiso 0.5 1 calc R U P A 1
H22B H 0.651035 0.497609 0.404975 0.083 Uiso 0.5 1 calc R U P A 1
H22C H 0.570528 0.553575 0.474446 0.083 Uiso 0.5 1 calc R U P A 1
O20B O 0.727(6) 0.663(4) 0.391(4) 0.0319(3) Uani 0.5 1 d . . P A 2
C21B C 0.559(2) 0.6276(13) 0.3908(5) 0.0431(16) Uani 0.5 1 d . . P A 2
H21C H 0.512378 0.641485 0.442609 0.052 Uiso 0.5 1 calc R U P A 2
H21D H 0.490333 0.657439 0.347586 0.052 Uiso 0.5 1 calc R U P A 2
C22B C 0.5584(8) 0.5308(5) 0.3781(3) 0.0556(11) Uani 0.5 1 d . . P A 2
H22D H 0.446295 0.508003 0.377877 0.083 Uiso 0.5 1 calc R U P A 2
H22E H 0.603195 0.517176 0.326462 0.083 Uiso 0.5 1 calc R U P A 2
H22F H 0.625205 0.501248 0.421333 0.083 Uiso 0.5 1 calc R U P A 2
C23 C 1.06780(17) 0.68104(10) 0.36142(9) 0.0263(3) Uani 1 1 d . . . . .
H23 H 1.176390 0.701491 0.373070 0.032 Uiso 1 1 calc R U . . .
C24 C 1.04296(17) 0.58176(10) 0.35728(9) 0.0256(3) Uani 1 1 d . . . . .
C25 C 1.11907(19) 0.52607(11) 0.41581(10) 0.0332(4) Uani 1 1 d . . . . .
H25 H 1.189928 0.552131 0.456753 0.040 Uiso 1 1 calc R U . . .
C26 C 1.0926(2) 0.43287(12) 0.41498(11) 0.0379(4) Uani 1 1 d . . . . .
H26 H 1.143898 0.395748 0.455725 0.046 Uiso 1 1 calc R U . . .
C27 C 0.9917(2) 0.39398(11) 0.35503(10) 0.0343(4) Uani 1 1 d . . . . .
H27 H 0.974210 0.330158 0.354239 0.041 Uiso 1 1 calc R U . . .
C28 C 0.9162(2) 0.44850(11) 0.29612(9) 0.0316(3) Uani 1 1 d . . . . .
H28 H 0.845970 0.421966 0.255167 0.038 Uiso 1 1 calc R U . . .
C29 C 0.94256(18) 0.54181(10) 0.29653(9) 0.0276(3) Uani 1 1 d . . . . .
H29 H 0.892016 0.578549 0.255278 0.033 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 1.2214(16) . ?
C2 N10 1.3770(18) . ?
C2 C3 1.4797(19) . ?
C3 C8 1.3856(19) . ?
C3 C4 1.387(2) . ?
C4 C5 1.389(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.389(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.505(2) . ?
C9 N10 1.4695(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N10 C11 1.4250(18) . ?
C11 C12 1.391(2) . ?
C11 C16 1.405(2) . ?
C12 C13 1.387(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.398(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.481(2) . ?
C17 C23 1.340(2) . ?
C17 C18 1.5030(19) . ?
C18 O19 1.2072(18) . ?
C18 O20A 1.33(6) . ?
C18 O20B 1.33(6) . ?
O20A C21A 1.48(6) . ?
C21A C22A 1.553(19) . ?
C21A H21A 0.9900 . ?
C21A H21B 0.9900 . ?
C22A H22A 0.9800 . ?
C22A H22B 0.9800 . ?
C22A H22C 0.9800 . ?
O20B C21B 1.47(6) . ?
C21B C22B 1.44(2) . ?
C21B H21C 0.9900 . ?
C21B H21D 0.9900 . ?
C22B H22D 0.9800 . ?
C22B H22E 0.9800 . ?
C22B H22F 0.9800 . ?
C23 C24 1.476(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.393(2) . ?
C24 C29 1.396(2) . ?
C25 C26 1.389(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.382(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.385(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.390(2) . ?
C28 H28 0.9500 . ?
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 125.76(13) . . ?
O1 C2 C3 128.39(13) . . ?
N10 C2 C3 105.85(11) . . ?
C8 C3 C4 122.19(13) . . ?
C8 C3 C2 109.23(12) . . ?
C4 C3 C2 128.55(13) . . ?
C3 C4 C5 117.80(14) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
C4 C5 C6 120.34(15) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 121.44(14) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 118.20(14) . . ?
C6 C7 H7 120.9 . . ?
C8 C7 H7 120.9 . . ?
C3 C8 C7 120.03(13) . . ?
C3 C8 C9 109.56(12) . . ?
C7 C8 C9 130.38(13) . . ?
N10 C9 C8 102.06(11) . . ?
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 122.78(11) . . ?
C2 N10 C9 113.20(11) . . ?
C11 N10 C9 123.96(11) . . ?
C12 C11 C16 120.68(13) . . ?
C12 C11 N10 120.15(13) . . ?
C16 C11 N10 119.12(13) . . ?
C13 C12 C11 120.13(14) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 120.09(15) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 119.77(15) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 121.31(14) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C11 118.00(14) . . ?
C15 C16 C17 120.51(13) . . ?
C11 C16 C17 121.49(13) . . ?
C23 C17 C16 122.19(13) . . ?
C23 C17 C18 121.77(13) . . ?
C16 C17 C18 116.00(12) . . ?
O19 C18 O20A 124(2) . . ?
O19 C18 O20B 124(2) . . ?
O19 C18 C17 123.58(14) . . ?
O20A C18 C17 112(2) . . ?
O20B C18 C17 112(2) . . ?
C18 O20A C21A 111(4) . . ?
O20A C21A C22A 102(2) . . ?
O20A C21A H21A 111.3 . . ?
C22A C21A H21A 111.3 . . ?
O20A C21A H21B 111.3 . . ?
C22A C21A H21B 111.3 . . ?
H21A C21A H21B 109.2 . . ?
C21A C22A H22A 109.5 . . ?
C21A C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
C21A C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
C18 O20B C21B 123(4) . . ?
C22B C21B O20B 110(3) . . ?
C22B C21B H21C 109.6 . . ?
O20B C21B H21C 109.6 . . ?
C22B C21B H21D 109.6 . . ?
O20B C21B H21D 109.6 . . ?
H21C C21B H21D 108.1 . . ?
C21B C22B H22D 109.5 . . ?
C21B C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
C21B C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
C17 C23 C24 126.73(13) . . ?
C17 C23 H23 116.6 . . ?
C24 C23 H23 116.6 . . ?
C25 C24 C29 118.69(14) . . ?
C25 C24 C23 119.68(14) . . ?
C29 C24 C23 121.62(13) . . ?
C26 C25 C24 120.74(15) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C27 C26 C25 120.17(15) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C28 119.67(15) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
C27 C28 C29 120.42(15) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C28 C29 C24 120.28(14) . . ?
C28 C29 H29 119.9 . . ?
C24 C29 H29 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C8 178.90(14) . . . . ?
N10 C2 C3 C8 -1.28(15) . . . . ?
O1 C2 C3 C4 -3.0(3) . . . . ?
N10 C2 C3 C4 176.78(14) . . . . ?
C8 C3 C4 C5 0.4(2) . . . . ?
C2 C3 C4 C5 -177.40(15) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 C7 -0.6(3) . . . . ?
C5 C6 C7 C8 0.4(2) . . . . ?
C4 C3 C8 C7 -0.7(2) . . . . ?
C2 C3 C8 C7 177.51(13) . . . . ?
C4 C3 C8 C9 -178.95(14) . . . . ?
C2 C3 C8 C9 -0.74(16) . . . . ?
C6 C7 C8 C3 0.3(2) . . . . ?
C6 C7 C8 C9 178.12(15) . . . . ?
C3 C8 C9 N10 2.31(15) . . . . ?
C7 C8 C9 N10 -175.71(15) . . . . ?
O1 C2 N10 C11 0.0(2) . . . . ?
C3 C2 N10 C11 -179.84(12) . . . . ?
O1 C2 N10 C9 -177.26(14) . . . . ?
C3 C2 N10 C9 2.91(15) . . . . ?
C8 C9 N10 C2 -3.26(15) . . . . ?
C8 C9 N10 C11 179.53(12) . . . . ?
C2 N10 C11 C12 -112.28(16) . . . . ?
C9 N10 C11 C12 64.68(19) . . . . ?
C2 N10 C11 C16 64.93(18) . . . . ?
C9 N10 C11 C16 -118.12(15) . . . . ?
C16 C11 C12 C13 0.2(2) . . . . ?
N10 C11 C12 C13 177.39(14) . . . . ?
C11 C12 C13 C14 -1.4(2) . . . . ?
C12 C13 C14 C15 1.3(3) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C14 C15 C16 C11 -1.0(2) . . . . ?
C14 C15 C16 C17 179.06(14) . . . . ?
C12 C11 C16 C15 1.0(2) . . . . ?
N10 C11 C16 C15 -176.21(13) . . . . ?
C12 C11 C16 C17 -179.13(13) . . . . ?
N10 C11 C16 C17 3.7(2) . . . . ?
C15 C16 C17 C23 43.9(2) . . . . ?
C11 C16 C17 C23 -136.03(15) . . . . ?
C15 C16 C17 C18 -133.99(14) . . . . ?
C11 C16 C17 C18 46.12(18) . . . . ?
C23 C17 C18 O19 -130.16(16) . . . . ?
C16 C17 C18 O19 47.70(19) . . . . ?
C23 C17 C18 O20A 50(3) . . . . ?
C16 C17 C18 O20A -132(3) . . . . ?
C23 C17 C18 O20B 50(3) . . . . ?
C16 C17 C18 O20B -132(3) . . . . ?
O19 C18 O20A C21A 14(5) . . . . ?
C17 C18 O20A C21A -167(2) . . . . ?
C18 O20A C21A C22A 160(3) . . . . ?
O19 C18 O20B C21B 2(6) . . . . ?
C17 C18 O20B C21B -179(4) . . . . ?
C18 O20B C21B C22B 116(4) . . . . ?
C16 C17 C23 C24 -173.93(13) . . . . ?
C18 C17 C23 C24 3.8(2) . . . . ?
C17 C23 C24 C25 -135.39(16) . . . . ?
C17 C23 C24 C29 43.6(2) . . . . ?
C29 C24 C25 C26 -1.6(2) . . . . ?
C23 C24 C25 C26 177.47(14) . . . . ?
C24 C25 C26 C27 1.0(2) . . . . ?
C25 C26 C27 C28 -0.5(2) . . . . ?
C26 C27 C28 C29 0.6(2) . . . . ?
C27 C28 C29 C24 -1.3(2) . . . . ?
C25 C24 C29 C28 1.7(2) . . . . ?
C23 C24 C29 C28 -177.32(14) . . . . ?

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR YYC448_2                                               #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
####################################################################### 
# 
# 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_YYC435
_database_code_depnum_ccdc_archive 'CCDC 1895844'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;Univ Rennes, CNRS, ISCR - UMR6226, F-35000 Rennes
France
;
_audit_update_record             
;
2019-02-06 deposited with the CCDC.	2019-08-02 downloaded from the CCDC.
;

_audit_creation_date             2018-11-20
_audit_creation_method           'SHELXL-2018_3, CRYSCALC (Oct. 2018)'
_audit_contact_author_adress     
;
     Centre de Diffractom\'etrie X
     UMR6226 CNRS Universit\'e de Rennes 1
     Institut des Sciences Chimiques de Rennes
     Campus de Beaulieu
     Avenue du G\'en\'eral Leclerc
     35042 RENNES Cedex France
;

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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H17 N O'
_chemical_formula_sum            'C22 H17 N O'
_chemical_formula_weight         311.36
_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                   6.0929(7)
_cell_length_b                   16.8891(17)
_cell_length_c                   15.9338(19)
_cell_angle_alpha                90
_cell_angle_beta                 91.658(5)
_cell_angle_gamma                90
_cell_volume                     1639.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    7683
_cell_measurement_theta_min      2.5576
_cell_measurement_theta_max      27.4971
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             656
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.077
_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  0.807
_exptl_absorpt_correction_T_max  0.995

#------------------------------------------------------------------------------#
#                               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  0.0292
_diffrn_reflns_av_uneti/neti     0.0317
_diffrn_reflns_number            12524
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.412
_diffrn_reflns_theta_max         27.570
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_reflns_number_total             3755
_reflns_number_gt                3067
_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, 2018)'

#------------------------------------------------------------------------------#
#                            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)+(0.0433P)²+0.6999P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018_3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0173(18)
_refine_ls_number_reflns         3755
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1180
_refine_ls_wR_factor_gt          0.1109
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.037

#...............................................................................
# .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 0.66193(16) 0.35914(7) 0.57042(7) 0.0365(3) Uani 1 1 d . . . . .
C2 C 0.8214(2) 0.36087(8) 0.52568(8) 0.0254(3) Uani 1 1 d . . . . .
C3 C 0.8647(2) 0.41447(8) 0.45481(9) 0.0289(3) Uani 1 1 d . . . . .
C4 C 0.7386(3) 0.47598(9) 0.42228(11) 0.0455(4) Uani 1 1 d . . . . .
H4 H 0.600524 0.488851 0.444930 0.055 Uiso 1 1 calc R U . . .
C5 C 0.8203(4) 0.51791(11) 0.35585(13) 0.0650(7) Uani 1 1 d . . . . .
H5 H 0.737303 0.560561 0.332461 0.078 Uiso 1 1 calc R U . . .
C6 C 1.0205(5) 0.49909(13) 0.32267(13) 0.0685(7) Uani 1 1 d . . . . .
H6 H 1.072970 0.529004 0.276916 0.082 Uiso 1 1 calc R U . . .
C7 C 1.1451(3) 0.43768(13) 0.35484(11) 0.0544(5) Uani 1 1 d . . . . .
H7 H 1.282290 0.424567 0.331593 0.065 Uiso 1 1 calc R U . . .
C8 C 1.0656(2) 0.39552(9) 0.42194(9) 0.0331(3) Uani 1 1 d . . . . .
C9 C 1.1659(2) 0.32821(9) 0.46960(9) 0.0332(3) Uani 1 1 d . . . . .
H9A H 1.190438 0.282130 0.432633 0.040 Uiso 1 1 calc R U . . .
H9B H 1.307025 0.343723 0.497270 0.040 Uiso 1 1 calc R U . . .
N10 N 0.99970(17) 0.31108(7) 0.53118(7) 0.0248(3) Uani 1 1 d . . . . .
C11 C 1.0236(2) 0.24729(8) 0.58872(8) 0.0276(3) Uani 1 1 d . . . . .
C12 C 1.2051(2) 0.24698(10) 0.64423(9) 0.0363(3) Uani 1 1 d . . . . .
H12 H 1.308826 0.288937 0.643244 0.044 Uiso 1 1 calc R U . . .
C13 C 1.2332(3) 0.18551(11) 0.70055(10) 0.0457(4) Uani 1 1 d . . . . .
H13 H 1.357157 0.184602 0.738088 0.055 Uiso 1 1 calc R U . . .
C14 C 1.0801(3) 0.12533(11) 0.70203(11) 0.0498(5) Uani 1 1 d . . . . .
H14 H 1.096828 0.083967 0.742113 0.060 Uiso 1 1 calc R U . . .
C15 C 0.9024(3) 0.12446(10) 0.64586(10) 0.0432(4) Uani 1 1 d . . . . .
H15 H 0.799348 0.082310 0.647696 0.052 Uiso 1 1 calc R U . . .
C16 C 0.8724(2) 0.18476(8) 0.58647(9) 0.0302(3) Uani 1 1 d . . . . .
C17 C 0.7045(2) 0.18078(8) 0.51864(9) 0.0302(3) Uani 1 1 d . . . . .
H17 H 0.711738 0.220842 0.476967 0.036 Uiso 1 1 calc R U . . .
C18 C 0.5438(2) 0.12833(8) 0.50815(9) 0.0308(3) Uani 1 1 d . . . . .
H18 H 0.526908 0.089191 0.550296 0.037 Uiso 1 1 calc R U . . .
C19 C 0.3904(2) 0.12715(8) 0.43522(9) 0.0287(3) Uani 1 1 d . . . . .
C20 C 0.4333(2) 0.16747(9) 0.36057(9) 0.0334(3) Uani 1 1 d . . . . .
H20 H 0.570241 0.193536 0.354782 0.040 Uiso 1 1 calc R U . . .
C21 C 0.2792(3) 0.16981(10) 0.29533(10) 0.0416(4) Uani 1 1 d . . . . .
H21 H 0.309837 0.197694 0.245233 0.050 Uiso 1 1 calc R U . . .
C22 C 0.0798(3) 0.13137(11) 0.30309(11) 0.0482(4) Uani 1 1 d . . . . .
H22 H -0.027628 0.133828 0.258745 0.058 Uiso 1 1 calc R U . . .
C23 C 0.0375(3) 0.08986(11) 0.37469(13) 0.0486(4) Uani 1 1 d . . . . .
H23 H -0.098079 0.062677 0.379362 0.058 Uiso 1 1 calc R U . . .
C24 C 0.1912(2) 0.08730(9) 0.44019(11) 0.0390(4) Uani 1 1 d . . . . .
H24 H 0.160447 0.057918 0.489310 0.047 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 1.2220(17) . ?
C2 N10 1.3746(16) . ?
C2 C3 1.477(2) . ?
C3 C8 1.383(2) . ?
C3 C4 1.384(2) . ?
C4 C5 1.379(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.376(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.384(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.488(2) . ?
C9 N10 1.4594(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N10 C11 1.4195(17) . ?
C11 C12 1.3957(19) . ?
C11 C16 1.401(2) . ?
C12 C13 1.380(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.399(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.4682(19) . ?
C17 C18 1.327(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.470(2) . ?
C18 H18 0.9500 . ?
C19 C24 1.392(2) . ?
C19 C20 1.402(2) . ?
C20 C21 1.381(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.370(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.383(2) . ?
C23 H23 0.9500 . ?
C24 H24 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 126.05(13) . . ?
O1 C2 C3 128.56(12) . . ?
N10 C2 C3 105.39(11) . . ?
C8 C3 C4 121.33(15) . . ?
C8 C3 C2 109.11(12) . . ?
C4 C3 C2 129.56(15) . . ?
C5 C4 C3 117.65(19) . . ?
C5 C4 H4 121.2 . . ?
C3 C4 H4 121.2 . . ?
C4 C5 C6 121.24(18) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 121.02(18) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 118.3(2) . . ?
C6 C7 H7 120.9 . . ?
C8 C7 H7 120.9 . . ?
C3 C8 C7 120.47(16) . . ?
C3 C8 C9 109.78(12) . . ?
C7 C8 C9 129.75(16) . . ?
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 124.87(11) . . ?
C2 N10 C9 113.48(11) . . ?
C11 N10 C9 121.64(11) . . ?
C12 C11 C16 121.44(13) . . ?
C12 C11 N10 118.48(13) . . ?
C16 C11 N10 120.02(12) . . ?
C13 C12 C11 119.74(15) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 119.61(15) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 120.87(15) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C14 C15 C16 120.92(16) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C11 117.30(13) . . ?
C15 C16 C17 122.63(14) . . ?
C11 C16 C17 119.81(12) . . ?
C18 C17 C16 128.25(14) . . ?
C18 C17 H17 115.9 . . ?
C16 C17 H17 115.9 . . ?
C17 C18 C19 123.94(13) . . ?
C17 C18 H18 118.0 . . ?
C19 C18 H18 118.0 . . ?
C24 C19 C20 117.87(14) . . ?
C24 C19 C18 119.79(14) . . ?
C20 C19 C18 122.29(13) . . ?
C21 C20 C19 120.87(15) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 119.88(16) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C23 C22 C21 120.02(15) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 120.34(16) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C19 120.97(16) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C8 179.93(13) . . . . ?
N10 C2 C3 C8 -0.76(14) . . . . ?
O1 C2 C3 C4 0.8(2) . . . . ?
N10 C2 C3 C4 -179.87(14) . . . . ?
C8 C3 C4 C5 -0.1(2) . . . . ?
C2 C3 C4 C5 178.95(14) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C4 C3 C8 C7 -0.4(2) . . . . ?
C2 C3 C8 C7 -179.61(13) . . . . ?
C4 C3 C8 C9 179.15(13) . . . . ?
C2 C3 C8 C9 -0.04(15) . . . . ?
C6 C7 C8 C3 0.7(2) . . . . ?
C6 C7 C8 C9 -178.76(16) . . . . ?
C3 C8 C9 N10 0.78(15) . . . . ?
C7 C8 C9 N10 -179.71(15) . . . . ?
O1 C2 N10 C11 2.2(2) . . . . ?
C3 C2 N10 C11 -177.12(11) . . . . ?
O1 C2 N10 C9 -179.35(13) . . . . ?
C3 C2 N10 C9 1.32(14) . . . . ?
C8 C9 N10 C2 -1.32(15) . . . . ?
C8 C9 N10 C11 177.18(12) . . . . ?
C2 N10 C11 C12 -121.81(15) . . . . ?
C9 N10 C11 C12 59.87(17) . . . . ?
C2 N10 C11 C16 61.00(18) . . . . ?
C9 N10 C11 C16 -117.32(15) . . . . ?
C16 C11 C12 C13 -2.5(2) . . . . ?
N10 C11 C12 C13 -179.65(14) . . . . ?
C11 C12 C13 C14 -0.7(2) . . . . ?
C12 C13 C14 C15 2.2(3) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C14 C15 C16 C11 -2.7(2) . . . . ?
C14 C15 C16 C17 171.45(16) . . . . ?
C12 C11 C16 C15 4.1(2) . . . . ?
N10 C11 C16 C15 -178.76(13) . . . . ?
C12 C11 C16 C17 -170.17(13) . . . . ?
N10 C11 C16 C17 6.9(2) . . . . ?
C15 C16 C17 C18 8.9(2) . . . . ?
C11 C16 C17 C18 -177.07(15) . . . . ?
C16 C17 C18 C19 -176.61(13) . . . . ?
C17 C18 C19 C24 -160.63(15) . . . . ?
C17 C18 C19 C20 17.0(2) . . . . ?
C24 C19 C20 C21 2.3(2) . . . . ?
C18 C19 C20 C21 -175.42(14) . . . . ?
C19 C20 C21 C22 -0.5(2) . . . . ?
C20 C21 C22 C23 -1.3(3) . . . . ?
C21 C22 C23 C24 1.3(3) . . . . ?
C22 C23 C24 C19 0.5(3) . . . . ?
C20 C19 C24 C23 -2.3(2) . . . . ?
C18 C19 C24 C23 175.46(14) . . . . ?

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR YYC435                                                 #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
####################################################################### 
# 
# 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_RGYYC460
_database_code_depnum_ccdc_archive 'CCDC 1895846'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;Univ Rennes, CNRS, ISCR - UMR6226, F-35000 Rennes
France
;
_audit_update_record             
;
2019-02-06 deposited with the CCDC.	2019-08-02 downloaded from the CCDC.
;


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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H17 N O3'
_chemical_formula_sum            'C19 H17 N O3'
_chemical_formula_weight         307.33
_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                   6.9823(8)
_cell_length_b                   10.9866(13)
_cell_length_c                   11.6209(15)
_cell_angle_alpha                110.950(4)
_cell_angle_beta                 97.555(4)
_cell_angle_gamma                105.365(5)
_cell_volume                     777.03(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    8455
_cell_measurement_theta_min      3.1259
_cell_measurement_theta_max      27.5196
_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          0.390
_exptl_crystal_size_min          0.150
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             324
_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  0.908
_exptl_absorpt_correction_T_max  0.987

#------------------------------------------------------------------------------#
#                               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  0.0403
_diffrn_reflns_av_uneti/neti     0.0354
_diffrn_reflns_number            14746
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.108
_diffrn_reflns_theta_max         27.503
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_reflns_number_total             3542
_reflns_number_gt                3000
_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, 2018)'

#------------------------------------------------------------------------------#
#                            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)+(0.0492P)²+0.3196P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3542
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1104
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.053

#...............................................................................
# .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 0.95134(14) 0.33557(10) 0.15052(9) 0.0262(2) Uani 1 1 d . . . . .
C2 C 0.77174(19) 0.32988(12) 0.13230(11) 0.0181(3) Uani 1 1 d . . . . .
C3 C 0.64045(18) 0.32724(12) 0.01918(11) 0.0170(2) Uani 1 1 d . . . . .
C4 C 0.6881(2) 0.33239(13) -0.09189(12) 0.0213(3) Uani 1 1 d . . . . .
H4 H 0.822348 0.340668 -0.103660 0.026 Uiso 1 1 calc R U . . .
C5 C 0.5334(2) 0.32504(14) -0.18499(12) 0.0235(3) Uani 1 1 d . . . . .
H5 H 0.560877 0.326135 -0.262616 0.028 Uiso 1 1 calc R U . . .
C6 C 0.3381(2) 0.31605(13) -0.16560(12) 0.0229(3) Uani 1 1 d . . . . .
H6 H 0.234595 0.311797 -0.230190 0.028 Uiso 1 1 calc R U . . .
C7 C 0.2920(2) 0.31320(13) -0.05380(12) 0.0209(3) Uani 1 1 d . . . . .
H7 H 0.159604 0.308850 -0.040254 0.025 Uiso 1 1 calc R U . . .
C8 C 0.44564(19) 0.31690(12) 0.03756(11) 0.0170(2) Uani 1 1 d . . . . .
C9 C 0.43847(18) 0.31321(13) 0.16457(11) 0.0192(3) Uani 1 1 d . . . . .
H9A H 0.403531 0.392145 0.219953 0.023 Uiso 1 1 calc R U . . .
H9B H 0.337906 0.225584 0.155422 0.023 Uiso 1 1 calc R U . . .
N10 N 0.64920(15) 0.32355(11) 0.21479(9) 0.0179(2) Uani 1 1 d . . . . .
C11 C 0.70095(18) 0.30163(12) 0.32748(11) 0.0162(2) Uani 1 1 d . . . . .
C12 C 0.74121(17) 0.40979(12) 0.44780(11) 0.0152(2) Uani 1 1 d . . . . .
C13 C 0.78253(18) 0.38293(12) 0.55585(11) 0.0171(2) Uani 1 1 d . . . . .
H13 H 0.812065 0.454759 0.638172 0.020 Uiso 1 1 calc R U . . .
C14 C 0.78068(19) 0.25274(13) 0.54364(12) 0.0194(3) Uani 1 1 d . . . . .
H14 H 0.807405 0.235540 0.617630 0.023 Uiso 1 1 calc R U . . .
C15 C 0.74002(19) 0.14668(13) 0.42391(12) 0.0207(3) Uani 1 1 d . . . . .
H15 H 0.739458 0.057787 0.417051 0.025 Uiso 1 1 calc R U . . .
C16 C 0.70023(19) 0.16916(12) 0.31427(12) 0.0196(3) Uani 1 1 d . . . . .
C17 C 0.6565(2) 0.05439(14) 0.18418(13) 0.0300(3) Uani 1 1 d . . . . .
H17A H 0.769588 0.075949 0.144965 0.045 Uiso 1 1 calc R U . . .
H17B H 0.528548 0.045727 0.130621 0.045 Uiso 1 1 calc R U . . .
H17C H 0.642819 -0.032980 0.192511 0.045 Uiso 1 1 calc R U . . .
C18 C 0.74200(18) 0.54725(12) 0.45874(11) 0.0163(2) Uani 1 1 d . . . . .
H18 H 0.709179 0.558051 0.381800 0.020 Uiso 1 1 calc R U . . .
C19 C 0.78485(18) 0.65828(12) 0.56747(11) 0.0166(2) Uani 1 1 d . . . . .
H19 H 0.816596 0.651324 0.646424 0.020 Uiso 1 1 calc R U . . .
C20 C 0.78336(18) 0.79165(12) 0.56614(12) 0.0178(3) Uani 1 1 d . . . . .
O21 O 0.75374(15) 0.81631(10) 0.47350(9) 0.0274(2) Uani 1 1 d . . . . .
O22 O 0.82305(15) 0.88718(9) 0.68644(9) 0.0244(2) Uani 1 1 d . . . . .
C23 C 0.8313(2) 1.02284(14) 0.69606(16) 0.0337(3) Uani 1 1 d . . . . .
H23A H 0.939251 1.057575 0.658337 0.051 Uiso 1 1 calc R U . . .
H23B H 0.861386 1.085716 0.785874 0.051 Uiso 1 1 calc R U . . .
H23C H 0.698779 1.017609 0.650540 0.051 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 1.2249(15) . ?
C2 N10 1.3739(16) . ?
C2 C3 1.4870(17) . ?
C3 C8 1.3858(17) . ?
C3 C4 1.3911(17) . ?
C4 C5 1.3885(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3950(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.3878(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.3876(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.4980(17) . ?
C9 N10 1.4686(15) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N10 C11 1.4321(15) . ?
C11 C12 1.4062(16) . ?
C11 C16 1.4064(17) . ?
C12 C13 1.4006(17) . ?
C12 C18 1.4681(16) . ?
C13 C14 1.3824(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3913(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.3892(18) . ?
C15 H15 0.9500 . ?
C16 C17 1.5099(17) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.3337(17) . ?
C18 H18 0.9500 . ?
C19 C20 1.4736(17) . ?
C19 H19 0.9500 . ?
C20 O21 1.2062(16) . ?
C20 O22 1.3518(15) . ?
O22 C23 1.4390(16) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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 125.93(11) . . ?
O1 C2 C3 128.39(11) . . ?
N10 C2 C3 105.69(10) . . ?
C8 C3 C4 121.30(11) . . ?
C8 C3 C2 109.00(11) . . ?
C4 C3 C2 129.70(11) . . ?
C5 C4 C3 117.91(12) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
C4 C5 C6 120.60(12) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 121.30(12) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C8 C7 C6 117.87(12) . . ?
C8 C7 H7 121.1 . . ?
C6 C7 H7 121.1 . . ?
C3 C8 C7 120.98(11) . . ?
C3 C8 C9 109.71(10) . . ?
C7 C8 C9 129.30(11) . . ?
N10 C9 C8 102.26(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 125.12(10) . . ?
C2 N10 C9 113.32(10) . . ?
C11 N10 C9 120.51(10) . . ?
C12 C11 C16 121.60(11) . . ?
C12 C11 N10 119.76(10) . . ?
C16 C11 N10 118.57(10) . . ?
C13 C12 C11 118.24(11) . . ?
C13 C12 C18 121.35(11) . . ?
C11 C12 C18 120.41(11) . . ?
C14 C13 C12 120.52(11) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.56(11) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 120.83(11) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C11 118.26(11) . . ?
C15 C16 C17 120.98(11) . . ?
C11 C16 C17 120.76(11) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C12 125.59(11) . . ?
C19 C18 H18 117.2 . . ?
C12 C18 H18 117.2 . . ?
C18 C19 C20 120.55(11) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
O21 C20 O22 123.27(11) . . ?
O21 C20 C19 126.62(11) . . ?
O22 C20 C19 110.10(10) . . ?
C20 O22 C23 114.59(11) . . ?
O22 C23 H23A 109.5 . . ?
O22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C8 178.47(12) . . . . ?
N10 C2 C3 C8 -1.11(13) . . . . ?
O1 C2 C3 C4 -1.0(2) . . . . ?
N10 C2 C3 C4 179.45(12) . . . . ?
C8 C3 C4 C5 -0.81(18) . . . . ?
C2 C3 C4 C5 178.57(12) . . . . ?
C3 C4 C5 C6 1.46(19) . . . . ?
C4 C5 C6 C7 -0.5(2) . . . . ?
C5 C6 C7 C8 -1.21(19) . . . . ?
C4 C3 C8 C7 -0.87(18) . . . . ?
C2 C3 C8 C7 179.63(11) . . . . ?
C4 C3 C8 C9 179.91(11) . . . . ?
C2 C3 C8 C9 0.41(13) . . . . ?
C6 C7 C8 C3 1.86(18) . . . . ?
C6 C7 C8 C9 -179.09(12) . . . . ?
C3 C8 C9 N10 0.39(13) . . . . ?
C7 C8 C9 N10 -178.74(12) . . . . ?
O1 C2 N10 C11 -9.9(2) . . . . ?
C3 C2 N10 C11 169.66(10) . . . . ?
O1 C2 N10 C9 -178.18(12) . . . . ?
C3 C2 N10 C9 1.41(13) . . . . ?
C8 C9 N10 C2 -1.15(13) . . . . ?
C8 C9 N10 C11 -170.00(10) . . . . ?
C2 N10 C11 C12 110.90(13) . . . . ?
C9 N10 C11 C12 -81.65(14) . . . . ?
C2 N10 C11 C16 -72.18(15) . . . . ?
C9 N10 C11 C16 95.28(13) . . . . ?
C16 C11 C12 C13 0.43(17) . . . . ?
N10 C11 C12 C13 177.26(10) . . . . ?
C16 C11 C12 C18 179.69(11) . . . . ?
N10 C11 C12 C18 -3.48(17) . . . . ?
C11 C12 C13 C14 -0.88(17) . . . . ?
C18 C12 C13 C14 179.87(11) . . . . ?
C12 C13 C14 C15 0.72(18) . . . . ?
C13 C14 C15 C16 -0.08(19) . . . . ?
C14 C15 C16 C11 -0.37(18) . . . . ?
C14 C15 C16 C17 179.87(12) . . . . ?
C12 C11 C16 C15 0.19(18) . . . . ?
N10 C11 C16 C15 -176.68(11) . . . . ?
C12 C11 C16 C17 179.95(12) . . . . ?
N10 C11 C16 C17 3.08(18) . . . . ?
C13 C12 C18 C19 1.63(19) . . . . ?
C11 C12 C18 C19 -177.60(11) . . . . ?
C12 C18 C19 C20 179.16(11) . . . . ?
C18 C19 C20 O21 -3.1(2) . . . . ?
C18 C19 C20 O22 177.60(11) . . . . ?
O21 C20 O22 C23 -1.13(18) . . . . ?
C19 C20 O22 C23 178.22(11) . . . . ?

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR RGYYC460                                               #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
####################################################################### 
# 
# 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_YYC456
_database_code_depnum_ccdc_archive 'CCDC 1895845'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;Univ Rennes, CNRS, ISCR - UMR6226, F-35000 Rennes
France
;
_audit_update_record             
;
2019-02-06 deposited with the CCDC.	2019-08-02 downloaded from the CCDC.
;

_audit_creation_date             2018-11-19
_audit_creation_method           'SHELXL-2018_3, CRYSCALC (Oct. 2018)'
_audit_contact_author_adress     
;
     Centre de Diffractom\'etrie X
     UMR6226 CNRS Universit\'e de Rennes 1
     Institut des Sciences Chimiques de Rennes
     Campus de Beaulieu
     Avenue du G\'en\'eral Leclerc
     35042 RENNES Cedex France
;

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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H17 N O4'
_chemical_formula_sum            'C19 H17 N O4'
_chemical_formula_weight         323.33
_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                   7.0659(7)
_cell_length_b                   10.6181(10)
_cell_length_c                   11.7282(13)
_cell_angle_alpha                111.090(3)
_cell_angle_beta                 100.172(4)
_cell_angle_gamma                102.895(4)
_cell_volume                     767.69(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    8559
_cell_measurement_theta_min      2.2255
_cell_measurement_theta_max      27.4942
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.100
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             340
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.099
_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  0.915
_exptl_absorpt_correction_T_max  0.990

#------------------------------------------------------------------------------#
#                               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  0.0375
_diffrn_reflns_av_uneti/neti     0.0338
_diffrn_reflns_number            14618
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.164
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_reflns_number_total             3516
_reflns_number_gt                2990
_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, 2018)'

#------------------------------------------------------------------------------#
#                            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)+(0.0488P)²+0.5270P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3516
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1065
_refine_ls_wR_factor_gt          0.0996
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_restrained_S_all      0.939
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.056

#...............................................................................
# .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 0.40831(14) 0.34830(11) 0.73706(9) 0.0217(2) Uani 1 1 d . . . . .
C2 C 0.58027(19) 0.34069(13) 0.75353(12) 0.0151(3) Uani 1 1 d . . . . .
C3 C 0.70684(19) 0.33033(13) 0.86366(12) 0.0155(3) Uani 1 1 d . . . . .
C4 C 0.6622(2) 0.32824(14) 0.97406(13) 0.0194(3) Uani 1 1 d . . . . .
H4 H 0.536894 0.336449 0.989230 0.023 Uiso 1 1 calc R U . . .
C5 C 0.8069(2) 0.31377(15) 1.06137(13) 0.0214(3) Uani 1 1 d . . . . .
H5 H 0.778997 0.309488 1.136443 0.026 Uiso 1 1 calc R U . . .
C6 C 0.9928(2) 0.30544(14) 1.04003(12) 0.0209(3) Uani 1 1 d . . . . .
H6 H 1.090177 0.296455 1.101267 0.025 Uiso 1 1 calc R U . . .
C7 C 1.0378(2) 0.31009(14) 0.93041(12) 0.0198(3) Uani 1 1 d . . . . .
H7 H 1.165507 0.306483 0.916847 0.024 Uiso 1 1 calc R U . . .
C8 C 0.8904(2) 0.32017(13) 0.84145(12) 0.0164(3) Uani 1 1 d . . . . .
C9 C 0.8944(2) 0.32267(15) 0.71466(12) 0.0188(3) Uani 1 1 d . . . . .
H9A H 1.006430 0.404039 0.724075 0.023 Uiso 1 1 calc R U . . .
H9B H 0.908336 0.233389 0.655720 0.023 Uiso 1 1 calc R U . . .
N10 N 0.69653(16) 0.33781(12) 0.67008(10) 0.0161(2) Uani 1 1 d . . . . .
C11 C 0.61623(19) 0.30693(13) 0.53853(12) 0.0153(3) Uani 1 1 d . . . . .
C12 C 0.4878(2) 0.17110(14) 0.45726(12) 0.0180(3) Uani 1 1 d . . . . .
H12 H 0.449529 0.103658 0.491293 0.022 Uiso 1 1 calc R U . . .
C13 C 0.4141(2) 0.13182(14) 0.32755(13) 0.0181(3) Uani 1 1 d . . . . .
H13 H 0.327475 0.038350 0.273036 0.022 Uiso 1 1 calc R U . . .
C14 C 0.46962(19) 0.23218(14) 0.27845(12) 0.0154(3) Uani 1 1 d . . . . .
C15 C 0.59606(19) 0.36898(13) 0.35917(12) 0.0148(2) Uani 1 1 d . . . . .
H15 H 0.630998 0.436698 0.324949 0.018 Uiso 1 1 calc R U . . .
C16 C 0.67286(18) 0.40878(13) 0.49005(12) 0.0138(2) Uani 1 1 d . . . . .
O17 O 0.40584(15) 0.20676(10) 0.15306(8) 0.0212(2) Uani 1 1 d . . . . .
C18 C 0.2903(2) 0.06413(16) 0.06583(14) 0.0288(3) Uani 1 1 d . . . . .
H18A H 0.368117 0.000042 0.072254 0.043 Uiso 1 1 calc R U . . .
H18B H 0.260157 0.057981 -0.021199 0.043 Uiso 1 1 calc R U . . .
H18C H 0.163411 0.036607 0.086639 0.043 Uiso 1 1 calc R U . . .
C19 C 0.80660(19) 0.55266(13) 0.57564(12) 0.0148(2) Uani 1 1 d . . . . .
H19 H 0.852647 0.572333 0.663260 0.018 Uiso 1 1 calc R U . . .
C20 C 0.86927(19) 0.65813(13) 0.54168(12) 0.0151(3) Uani 1 1 d . . . . .
H20 H 0.829364 0.642232 0.454671 0.018 Uiso 1 1 calc R U . . .
C21 C 1.00033(19) 0.79969(13) 0.63809(12) 0.0154(3) Uani 1 1 d . . . . .
O22 O 1.05989(16) 0.83405(10) 0.75136(9) 0.0251(2) Uani 1 1 d . . . . .
O23 O 1.04411(15) 0.88993(10) 0.58266(9) 0.0203(2) Uani 1 1 d . . . . .
C24 C 1.1650(2) 1.03350(14) 0.66857(14) 0.0247(3) Uani 1 1 d . . . . .
H24A H 1.098461 1.071603 0.733867 0.037 Uiso 1 1 calc R U . . .
H24B H 1.179829 1.092476 0.620828 0.037 Uiso 1 1 calc R U . . .
H24C H 1.298911 1.034014 0.709408 0.037 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(16) . ?
C2 N10 1.3810(16) . ?
C2 C3 1.4895(17) . ?
C3 C8 1.3867(18) . ?
C3 C4 1.3921(18) . ?
C4 C5 1.3896(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.3928(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.3898(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.5020(17) . ?
C9 N10 1.4688(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N10 C11 1.4331(16) . ?
C11 C12 1.3905(18) . ?
C11 C16 1.4080(17) . ?
C12 C13 1.3877(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.3986(18) . ?
C13 H13 0.9500 . ?
C14 O17 1.3654(15) . ?
C14 C15 1.3917(17) . ?
C15 C16 1.4020(17) . ?
C15 H15 0.9500 . ?
C16 C19 1.4669(17) . ?
O17 C18 1.4301(17) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.3308(18) . ?
C19 H19 0.9500 . ?
C20 C21 1.4768(17) . ?
C20 H20 0.9500 . ?
C21 O22 1.2084(16) . ?
C21 O23 1.3503(15) . ?
O23 C24 1.4416(16) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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 125.95(12) . . ?
O1 C2 C3 128.33(12) . . ?
N10 C2 C3 105.72(11) . . ?
C8 C3 C4 121.47(12) . . ?
C8 C3 C2 109.03(11) . . ?
C4 C3 C2 129.49(12) . . ?
C5 C4 C3 117.86(13) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
C4 C5 C6 120.76(12) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 121.06(12) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C6 118.01(13) . . ?
C8 C7 H7 121.0 . . ?
C6 C7 H7 121.0 . . ?
C3 C8 C7 120.78(12) . . ?
C3 C8 C9 109.68(11) . . ?
C7 C8 C9 129.54(12) . . ?
N10 C9 C8 102.44(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 123.89(11) . . ?
C2 N10 C9 113.11(10) . . ?
C11 N10 C9 120.22(10) . . ?
C12 C11 C16 120.07(11) . . ?
C12 C11 N10 118.59(11) . . ?
C16 C11 N10 121.26(11) . . ?
C13 C12 C11 121.48(12) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 118.87(12) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
O17 C14 C15 115.54(11) . . ?
O17 C14 C13 124.34(11) . . ?
C15 C14 C13 120.12(11) . . ?
C14 C15 C16 121.26(11) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C11 118.18(11) . . ?
C15 C16 C19 121.56(11) . . ?
C11 C16 C19 120.26(11) . . ?
C14 O17 C18 116.97(11) . . ?
O17 C18 H18A 109.5 . . ?
O17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C16 125.91(12) . . ?
C20 C19 H19 117.0 . . ?
C16 C19 H19 117.0 . . ?
C19 C20 C21 120.57(11) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
O22 C21 O23 123.30(12) . . ?
O22 C21 C20 126.26(12) . . ?
O23 C21 C20 110.43(11) . . ?
C21 O23 C24 115.38(10) . . ?
O23 C24 H24A 109.5 . . ?
O23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C8 178.43(13) . . . . ?
N10 C2 C3 C8 -0.66(14) . . . . ?
O1 C2 C3 C4 -0.7(2) . . . . ?
N10 C2 C3 C4 -179.82(13) . . . . ?
C8 C3 C4 C5 -0.8(2) . . . . ?
C2 C3 C4 C5 178.26(12) . . . . ?
C3 C4 C5 C6 1.7(2) . . . . ?
C4 C5 C6 C7 -0.6(2) . . . . ?
C5 C6 C7 C8 -1.4(2) . . . . ?
C4 C3 C8 C7 -1.2(2) . . . . ?
C2 C3 C8 C7 179.59(12) . . . . ?
C4 C3 C8 C9 179.00(12) . . . . ?
C2 C3 C8 C9 -0.24(14) . . . . ?
C6 C7 C8 C3 2.2(2) . . . . ?
C6 C7 C8 C9 -177.97(13) . . . . ?
C3 C8 C9 N10 0.98(14) . . . . ?
C7 C8 C9 N10 -178.83(13) . . . . ?
O1 C2 N10 C11 -16.7(2) . . . . ?
C3 C2 N10 C11 162.42(11) . . . . ?
O1 C2 N10 C9 -177.76(12) . . . . ?
C3 C2 N10 C9 1.35(14) . . . . ?
C8 C9 N10 C2 -1.46(14) . . . . ?
C8 C9 N10 C11 -163.29(11) . . . . ?
C2 N10 C11 C12 -66.42(17) . . . . ?
C9 N10 C11 C12 93.37(15) . . . . ?
C2 N10 C11 C16 116.71(14) . . . . ?
C9 N10 C11 C16 -83.50(15) . . . . ?
C16 C11 C12 C13 0.7(2) . . . . ?
N10 C11 C12 C13 -176.25(11) . . . . ?
C11 C12 C13 C14 -0.6(2) . . . . ?
C12 C13 C14 O17 -179.43(12) . . . . ?
C12 C13 C14 C15 -0.22(19) . . . . ?
O17 C14 C15 C16 -179.73(11) . . . . ?
C13 C14 C15 C16 1.00(19) . . . . ?
C14 C15 C16 C11 -0.92(18) . . . . ?
C14 C15 C16 C19 179.85(11) . . . . ?
C12 C11 C16 C15 0.10(18) . . . . ?
N10 C11 C16 C15 176.93(11) . . . . ?
C12 C11 C16 C19 179.34(12) . . . . ?
N10 C11 C16 C19 -3.83(18) . . . . ?
C15 C14 O17 C18 174.70(12) . . . . ?
C13 C14 O17 C18 -6.06(19) . . . . ?
C15 C16 C19 C20 -0.2(2) . . . . ?
C11 C16 C19 C20 -179.41(12) . . . . ?
C16 C19 C20 C21 178.48(12) . . . . ?
C19 C20 C21 O22 -0.8(2) . . . . ?
C19 C20 C21 O23 -179.65(11) . . . . ?
O22 C21 O23 C24 -1.30(19) . . . . ?
C20 C21 O23 C24 177.61(11) . . . . ?

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#===END OF CIF FILE FOR YYC456                                                 #
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