# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_1_190K
_database_code_depnum_ccdc_archive 'CCDC 1859278'
_audit_update_record             
;
2018-07-30 deposited with the CCDC.
2018-09-14 downloaded from the CCDC.
;

_audit_creation_date             2018-05-21T15:57:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C36 H32 N4 O4'
_chemical_formula_weight         584.65

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.3235(6)
_cell_length_b                   9.7491(3)
_cell_length_c                   14.2452(8)
_cell_angle_alpha                90
_cell_angle_beta                 111.822(2)
_cell_angle_gamma                90
_cell_volume                     1459.90(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    1744
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      26.42

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

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.355
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.169
_exptl_crystal_density_diffrn    1.33
_exptl_crystal_F_000             616

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

_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.7806
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.985

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

_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_number            7726
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.977
_diffrn_reflns_theta_max         27.527
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             3356
_reflns_number_gt                2300
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²+0.3269P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3356
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.078
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.115
_refine_ls_wR_factor_gt          0.0992
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.2
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.045

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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 0 '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 0.006 '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 0.09083(12) 0.15056(13) 0.47783(10) 0.0372(3) Uani 1 1 d . . . . .
H1 H 0.023983 0.174804 0.485799 0.056 Uiso 1 1 calc R U . . .
O2 O -0.06302(13) 0.46664(14) 0.19924(10) 0.0449(4) Uani 1 1 d . . . . .
H2A H -0.120092 0.479389 0.222717 0.067 Uiso 1 1 calc R U . . .
N1 N 0.11343(15) 0.77802(15) 0.47693(11) 0.0332(4) Uani 1 1 d . . . . .
N2 N 0.73689(15) 0.52865(15) 0.26091(11) 0.0336(4) Uani 1 1 d . . . . .
C1 C 0.09774(16) 0.21412(17) 0.39550(13) 0.0280(4) Uani 1 1 d . . . . .
C2 C 0.00803(16) 0.30911(16) 0.33940(13) 0.0267(4) Uani 1 1 d . . . . .
H2 H -0.062118 0.3313 0.357875 0.032 Uiso 1 1 calc R U . . .
C3 C 0.02097(17) 0.37159(18) 0.25633(13) 0.0307(4) Uani 1 1 d . . . . .
C4 C 0.12334(17) 0.33947(19) 0.22903(14) 0.0354(4) Uani 1 1 d . . . . .
H4 H 0.132453 0.382379 0.172222 0.042 Uiso 1 1 calc R U . . .
C5 C 0.21160(17) 0.24460(19) 0.28528(14) 0.0361(5) Uani 1 1 d . . . . .
H5 H 0.281343 0.222039 0.266387 0.043 Uiso 1 1 calc R U . . .
C6 C 0.20066(17) 0.18170(19) 0.36859(14) 0.0333(4) Uani 1 1 d . . . . .
H6 H 0.262603 0.117126 0.407015 0.04 Uiso 1 1 calc R U . . .
C7 C 0.22304(19) 0.84455(18) 0.52168(14) 0.0348(4) Uani 1 1 d . . . . .
H7 H 0.221241 0.930244 0.552874 0.042 Uiso 1 1 calc R U . . .
C8 C 0.33882(17) 0.79562(17) 0.52510(13) 0.0301(4) Uani 1 1 d . . . . .
H8 H 0.414237 0.846861 0.55835 0.036 Uiso 1 1 calc R U . . .
C9 C 0.34466(15) 0.67109(15) 0.47970(12) 0.0231(4) Uani 1 1 d . . . . .
C10 C 0.23069(16) 0.60419(18) 0.43064(14) 0.0313(4) Uani 1 1 d . . . . .
H10 H 0.229111 0.520145 0.396443 0.038 Uiso 1 1 calc R U . . .
C11 C 0.11935(17) 0.65999(19) 0.43155(15) 0.0356(4) Uani 1 1 d . . . . .
H11 H 0.042313 0.611576 0.397912 0.043 Uiso 1 1 calc R U . . .
C12 C 0.47148(15) 0.60943(16) 0.49405(12) 0.0218(3) Uani 1 1 d . . . . .
H12 H 0.536371 0.68283 0.50267 0.026 Uiso 1 1 calc R U . . .
C13 C 0.47788(15) 0.50046(16) 0.41714(12) 0.0220(3) Uani 1 1 d . . . . .
H13 H 0.390166 0.475671 0.369997 0.026 Uiso 1 1 calc R U . . .
C14 C 0.56278(15) 0.52350(16) 0.35893(12) 0.0224(3) Uani 1 1 d . . . . .
C15 C 0.54508(17) 0.44597(18) 0.27350(13) 0.0315(4) Uani 1 1 d . . . . .
H15 H 0.472335 0.388737 0.246359 0.038 Uiso 1 1 calc R U . . .
C16 C 0.63274(19) 0.45161(19) 0.22769(14) 0.0374(5) Uani 1 1 d . . . . .
H16 H 0.617893 0.397327 0.169015 0.045 Uiso 1 1 calc R U . . .
C17 C 0.75020(17) 0.60843(18) 0.33950(14) 0.0335(4) Uani 1 1 d . . . . .
H17 H 0.821595 0.668086 0.362726 0.04 Uiso 1 1 calc R U . . .
C18 C 0.66663(16) 0.61034(18) 0.38990(13) 0.0296(4) Uani 1 1 d . . . . .
H18 H 0.680578 0.670822 0.44529 0.036 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 C1 1.354(2) . ?
O1 H1 0.84 . ?
O2 C3 1.360(2) . ?
O2 H2A 0.84 . ?
N1 C11 1.334(2) . ?
N1 C7 1.334(2) . ?
N2 C17 1.325(2) . ?
N2 C16 1.328(2) . ?
C1 C2 1.387(2) . ?
C1 C6 1.392(2) . ?
C2 C3 1.386(2) . ?
C2 H2 0.95 . ?
C3 C4 1.389(2) . ?
C4 C5 1.379(3) . ?
C4 H4 0.95 . ?
C5 C6 1.382(3) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C8 1.379(2) . ?
C7 H7 0.95 . ?
C8 C9 1.389(2) . ?
C8 H8 0.95 . ?
C9 C10 1.382(2) . ?
C9 C12 1.499(2) . ?
C10 C11 1.378(2) . ?
C10 H10 0.95 . ?
C11 H11 0.95 . ?
C12 C13 1.547(2) . ?
C12 C13 1.593(2) 3_666 ?
C12 H12 1 . ?
C13 C14 1.502(2) . ?
C13 H13 1 . ?
C14 C18 1.381(2) . ?
C14 C15 1.383(2) . ?
C15 C16 1.377(2) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C17 C18 1.384(2) . ?
C17 H17 0.95 . ?
C18 H18 0.95 . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 116.47(15) . . ?
C17 N2 C16 116.10(14) . . ?
O1 C1 C2 122.59(14) . . ?
O1 C1 C6 117.29(16) . . ?
C2 C1 C6 120.11(16) . . ?
C3 C2 C1 119.86(15) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
O2 C3 C2 122.51(15) . . ?
O2 C3 C4 117.21(16) . . ?
C2 C3 C4 120.28(17) . . ?
C5 C4 C3 119.26(17) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.32(16) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 119.17(17) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
N1 C7 C8 123.52(16) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C9 119.69(17) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 116.81(15) . . ?
C10 C9 C12 123.16(14) . . ?
C8 C9 C12 119.75(15) . . ?
C11 C10 C9 119.66(16) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
N1 C11 C10 123.80(17) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C9 C12 C13 118.26(13) . . ?
C9 C12 C13 114.95(12) . 3_666 ?
C13 C12 C13 90.16(11) . 3_666 ?
C9 C12 H12 110.6 . . ?
C13 C12 H12 110.6 . . ?
C13 C12 H12 110.6 3_666 . ?
C14 C13 C12 119.77(13) . . ?
C14 C13 C12 115.07(12) . 3_666 ?
C12 C13 C12 89.84(11) . 3_666 ?
C14 C13 H13 110.2 . . ?
C12 C13 H13 110.2 . . ?
C12 C13 H13 110.2 3_666 . ?
C18 C14 C15 116.35(14) . . ?
C18 C14 C13 123.99(14) . . ?
C15 C14 C13 119.42(15) . . ?
C16 C15 C14 120.08(17) . . ?
C16 C15 H15 120 . . ?
C14 C15 H15 120 . . ?
N2 C16 C15 123.70(16) . . ?
N2 C16 H16 118.1 . . ?
C15 C16 H16 118.1 . . ?
N2 C17 C18 124.14(17) . . ?
N2 C17 H17 117.9 . . ?
C18 C17 H17 117.9 . . ?
C14 C18 C17 119.40(16) . . ?
C14 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.84 1.88 2.7125(18) 171.8 3_566
O2 H2A N2 0.84 1.95 2.7840(18) 171.5 1_455


_exptl_crystal_recrystallization_method Photoreaction
####################################################################### 
# 
# 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_1_210K
_database_code_depnum_ccdc_archive 'CCDC 1859279'
_audit_update_record             
;
2018-07-30 deposited with the CCDC.
2018-09-14 downloaded from the CCDC.
;

_audit_creation_date             2018-05-21T15:57:38-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C36 H32 N4 O4'
_chemical_formula_weight         584.65

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.3155(9)
_cell_length_b                   9.7527(5)
_cell_length_c                   14.2477(11)
_cell_angle_alpha                90
_cell_angle_beta                 111.746(3)
_cell_angle_gamma                90
_cell_volume                     1460.43(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    1654
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      26.43

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

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.355
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.169
_exptl_crystal_density_diffrn    1.33
_exptl_crystal_F_000             616

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

_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.7806
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.985

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

_diffrn_ambient_temperature      210(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_number            7750
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.978
_diffrn_reflns_theta_max         27.536
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             3364
_reflns_number_gt                2225
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0454P)²+0.1479P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3364
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1136
_refine_ls_wR_factor_gt          0.0979
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.043

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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 0 '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 0.006 '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 0.09071(12) 0.15031(12) 0.47774(10) 0.0414(3) Uani 1 1 d . . . . .
H1 H 0.025006 0.174893 0.485993 0.062 Uiso 1 1 calc R U . . .
O2 O -0.06215(13) 0.46638(14) 0.19998(11) 0.0500(4) Uani 1 1 d . . . . .
H2A H -0.120177 0.476881 0.221759 0.075 Uiso 1 1 calc R U . . .
N1 N 0.11378(15) 0.77806(15) 0.47698(11) 0.0369(4) Uani 1 1 d . . . . .
N2 N 0.73695(15) 0.52830(15) 0.26104(12) 0.0376(4) Uani 1 1 d . . . . .
C1 C 0.09780(16) 0.21388(16) 0.39573(13) 0.0308(4) Uani 1 1 d . . . . .
C2 C 0.00829(16) 0.30885(16) 0.33968(12) 0.0297(4) Uani 1 1 d . . . . .
H2 H -0.061318 0.330667 0.357837 0.036 Uiso 1 1 calc R U . . .
C3 C 0.02151(17) 0.37149(17) 0.25698(13) 0.0341(4) Uani 1 1 d . . . . .
C4 C 0.12428(18) 0.33923(18) 0.22989(15) 0.0396(5) Uani 1 1 d . . . . .
H4 H 0.133726 0.381849 0.173911 0.047 Uiso 1 1 calc R U . . .
C5 C 0.21192(18) 0.24435(19) 0.28583(15) 0.0407(5) Uani 1 1 d . . . . .
H5 H 0.280823 0.221731 0.266999 0.049 Uiso 1 1 calc R U . . .
C6 C 0.20100(17) 0.18171(18) 0.36884(14) 0.0375(4) Uani 1 1 d . . . . .
H6 H 0.262422 0.118026 0.4069 0.045 Uiso 1 1 calc R U . . .
C7 C 0.22340(19) 0.84409(18) 0.52195(14) 0.0390(5) Uani 1 1 d . . . . .
H7 H 0.221702 0.928671 0.553063 0.047 Uiso 1 1 calc R U . . .
C8 C 0.33884(17) 0.79524(16) 0.52530(13) 0.0329(4) Uani 1 1 d . . . . .
H8 H 0.413406 0.845934 0.558322 0.039 Uiso 1 1 calc R U . . .
C9 C 0.34521(15) 0.67127(15) 0.47999(12) 0.0252(4) Uani 1 1 d . . . . .
C10 C 0.23110(16) 0.60496(17) 0.43085(14) 0.0347(4) Uani 1 1 d . . . . .
H10 H 0.229424 0.521863 0.396955 0.042 Uiso 1 1 calc R U . . .
C11 C 0.11990(17) 0.66082(18) 0.43163(15) 0.0401(5) Uani 1 1 d . . . . .
H11 H 0.043646 0.613153 0.398054 0.048 Uiso 1 1 calc R U . . .
C12 C 0.47160(14) 0.60915(15) 0.49395(12) 0.0245(3) Uani 1 1 d . . . . .
H12 H 0.536031 0.681597 0.502414 0.029 Uiso 1 1 calc R U . . .
C13 C 0.47799(15) 0.50039(15) 0.41739(12) 0.0244(3) Uani 1 1 d . . . . .
H13 H 0.391167 0.475895 0.370753 0.029 Uiso 1 1 calc R U . . .
C14 C 0.56316(15) 0.52359(15) 0.35919(12) 0.0253(4) Uani 1 1 d . . . . .
C15 C 0.54522(17) 0.44622(18) 0.27385(13) 0.0357(4) Uani 1 1 d . . . . .
H15 H 0.472897 0.390124 0.246889 0.043 Uiso 1 1 calc R U . . .
C16 C 0.63305(19) 0.45116(19) 0.22825(14) 0.0416(5) Uani 1 1 d . . . . .
H16 H 0.618656 0.396798 0.170584 0.05 Uiso 1 1 calc R U . . .
C17 C 0.75028(17) 0.60814(18) 0.33968(14) 0.0380(4) Uani 1 1 d . . . . .
H17 H 0.82093 0.667152 0.362681 0.046 Uiso 1 1 calc R U . . .
C18 C 0.66660(16) 0.60980(17) 0.38981(13) 0.0333(4) Uani 1 1 d . . . . .
H18 H 0.680329 0.669602 0.444593 0.04 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 C1 1.351(2) . ?
O1 H1 0.83 . ?
O2 C3 1.357(2) . ?
O2 H2A 0.83 . ?
N1 C11 1.328(2) . ?
N1 C7 1.332(2) . ?
N2 C17 1.326(2) . ?
N2 C16 1.326(2) . ?
C1 C2 1.386(2) . ?
C1 C6 1.393(2) . ?
C2 C3 1.384(2) . ?
C2 H2 0.94 . ?
C3 C4 1.390(2) . ?
C4 C5 1.374(3) . ?
C4 H4 0.94 . ?
C5 C6 1.377(3) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.375(2) . ?
C7 H7 0.94 . ?
C8 C9 1.385(2) . ?
C8 H8 0.94 . ?
C9 C10 1.381(2) . ?
C9 C12 1.497(2) . ?
C10 C11 1.375(2) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.542(2) . ?
C12 C13 1.590(2) 3_666 ?
C12 H12 0.99 . ?
C13 C14 1.503(2) . ?
C13 H13 0.99 . ?
C14 C18 1.374(2) . ?
C14 C15 1.381(2) . ?
C15 C16 1.375(2) . ?
C15 H15 0.94 . ?
C16 H16 0.94 . ?
C17 C18 1.381(2) . ?
C17 H17 0.94 . ?
C18 H18 0.94 . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 116.31(15) . . ?
C17 N2 C16 116.04(14) . . ?
O1 C1 C2 122.68(14) . . ?
O1 C1 C6 117.32(16) . . ?
C2 C1 C6 120.00(16) . . ?
C3 C2 C1 119.94(15) . . ?
C3 C2 H2 120 . . ?
C1 C2 H2 120 . . ?
O2 C3 C2 122.62(15) . . ?
O2 C3 C4 117.25(16) . . ?
C2 C3 C4 120.13(17) . . ?
C5 C4 C3 119.30(17) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.45(16) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 119.18(17) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
N1 C7 C8 123.54(16) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C9 119.96(17) . . ?
C7 C8 H8 120 . . ?
C9 C8 H8 120 . . ?
C10 C9 C8 116.42(15) . . ?
C10 C9 C12 123.08(14) . . ?
C8 C9 C12 120.23(15) . . ?
C11 C10 C9 119.81(16) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
N1 C11 C10 123.92(18) . . ?
N1 C11 H11 118 . . ?
C10 C11 H11 118 . . ?
C9 C12 C13 118.50(13) . . ?
C9 C12 C13 114.91(12) . 3_666 ?
C13 C12 C13 90.16(11) . 3_666 ?
C9 C12 H12 110.6 . . ?
C13 C12 H12 110.6 . . ?
C13 C12 H12 110.6 3_666 . ?
C14 C13 C12 119.62(13) . . ?
C14 C13 C12 115.14(12) . 3_666 ?
C12 C13 C12 89.84(11) . 3_666 ?
C14 C13 H13 110.2 . . ?
C12 C13 H13 110.2 . . ?
C12 C13 H13 110.2 3_666 . ?
C18 C14 C15 116.36(14) . . ?
C18 C14 C13 124.16(14) . . ?
C15 C14 C13 119.24(14) . . ?
C16 C15 C14 120.05(17) . . ?
C16 C15 H15 120 . . ?
C14 C15 H15 120 . . ?
N2 C16 C15 123.72(16) . . ?
N2 C16 H16 118.1 . . ?
C15 C16 H16 118.1 . . ?
N2 C17 C18 123.95(17) . . ?
N2 C17 H17 118 . . ?
C18 C17 H17 118 . . ?
C14 C18 C17 119.67(16) . . ?
C14 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.83 1.89 2.7139(18) 172.2 3_566
O2 H2A N2 0.83 1.96 2.7847(18) 171.1 1_455


_exptl_crystal_recrystallization_method Photoreaction
####################################################################### 
# 
# 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_1_270K
_database_code_depnum_ccdc_archive 'CCDC 1859282'
_audit_update_record             
;
2018-07-30 deposited with the CCDC.
2018-09-14 downloaded from the CCDC.
;

_audit_creation_date             2018-05-21T15:59:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C36 H32 N4 O4'
_chemical_formula_weight         584.65

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.3142(10)
_cell_length_b                   9.7891(6)
_cell_length_c                   14.2833(13)
_cell_angle_alpha                90
_cell_angle_beta                 111.607(4)
_cell_angle_gamma                90
_cell_volume                     1470.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    270(2)
_cell_measurement_reflns_used    1427
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      26.39

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

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.355
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.169
_exptl_crystal_density_diffrn    1.32
_exptl_crystal_F_000             616

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

_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.7806
_shelx_estimated_absorpt_T_min   0.97
_shelx_estimated_absorpt_T_max   0.985

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

_diffrn_ambient_temperature      270(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_number            7746
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.978
_diffrn_reflns_theta_max         27.557
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.993
_reflns_Friedel_coverage         0
_reflns_number_total             3381
_reflns_number_gt                2035
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²+0.1301P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3381
_refine_ls_number_parameters     201
_refine_ls_number_restraints     153
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1209
_refine_ls_wR_factor_gt          0.1012
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      0.99
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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 0 '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 0.006 '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 0.09031(14) 0.14988(14) 0.47750(11) 0.0536(4) Uani 1 1 d . . . . .
H1 H 0.025984 0.175069 0.486182 0.08 Uiso 1 1 calc R U . . .
O2 O -0.06001(15) 0.46604(17) 0.20170(12) 0.0652(5) Uani 1 1 d . . . . .
H2A H -0.117121 0.476917 0.223396 0.098 Uiso 1 1 calc R U . . .
N1 N 0.11510(17) 0.77902(17) 0.47746(13) 0.0472(4) Uani 1 1 d . . . . .
N2 N 0.73793(17) 0.52751(17) 0.26197(13) 0.0493(5) Uani 1 1 d . . . . .
C1 C 0.09802(18) 0.21375(18) 0.39602(15) 0.0400(5) Uani 1 1 d . . . . .
C2 C 0.00928(18) 0.30847(18) 0.34055(14) 0.0383(5) Uani 1 1 d . . . . .
H2 H -0.05961 0.330235 0.358444 0.046 Uiso 1 1 calc R U . . .
C3 C 0.02324(19) 0.3708(2) 0.25839(15) 0.0436(5) Uani 1 1 d . . . . .
C4 C 0.1257(2) 0.3385(2) 0.23146(16) 0.0508(5) Uani 1 1 d . . . . .
H4 H 0.135396 0.380411 0.176297 0.061 Uiso 1 1 calc R U . . .
C5 C 0.2125(2) 0.2441(2) 0.28712(17) 0.0522(6) Uani 1 1 d . . . . .
H5 H 0.281007 0.221954 0.26887 0.063 Uiso 1 1 calc R U . . .
C6 C 0.20078(19) 0.1813(2) 0.36911(16) 0.0484(5) Uani 1 1 d . . . . .
H6 H 0.260916 0.117832 0.406245 0.058 Uiso 1 1 calc R U . . .
C7 C 0.2250(2) 0.8434(2) 0.52247(16) 0.0497(6) Uani 1 1 d . . . . .
H7 H 0.223759 0.926581 0.553619 0.06 Uiso 1 1 calc R U . . .
C8 C 0.34000(19) 0.79446(18) 0.52568(15) 0.0422(5) Uani 1 1 d . . . . .
H8 H 0.413909 0.843963 0.558442 0.051 Uiso 1 1 calc R U . . .
C9 C 0.34585(17) 0.67140(17) 0.48013(13) 0.0320(4) Uani 1 1 d . . . . .
C10 C 0.23183(18) 0.60695(19) 0.43066(15) 0.0434(5) Uani 1 1 d . . . . .
H10 H 0.22971 0.525588 0.396471 0.052 Uiso 1 1 calc R U . . .
C11 C 0.12110(19) 0.6629(2) 0.43182(17) 0.0508(5) Uani 1 1 d . . . . .
H11 H 0.045585 0.616328 0.398485 0.061 Uiso 1 1 calc R U . . .
C12 C 0.47195(16) 0.60861(17) 0.49404(13) 0.0308(4) Uani 1 1 d . . . . .
H12 H 0.536046 0.679749 0.5026 0.037 Uiso 1 1 calc R U . . .
C13 C 0.47840(16) 0.50066(17) 0.41758(13) 0.0310(4) Uani 1 1 d . . . . .
H13 H 0.392542 0.47679 0.371519 0.037 Uiso 1 1 calc R U . . .
C14 C 0.56391(16) 0.52308(17) 0.35969(13) 0.0321(4) Uani 1 1 d . . . . .
C15 C 0.54659(19) 0.4459(2) 0.27512(15) 0.0457(5) Uani 1 1 d . . . . .
H15 H 0.475439 0.390095 0.248876 0.055 Uiso 1 1 calc R U . . .
C16 C 0.6340(2) 0.4511(2) 0.22945(16) 0.0535(6) Uani 1 1 d . . . . .
H16 H 0.619441 0.397969 0.172318 0.064 Uiso 1 1 calc R U . . .
C17 C 0.7507(2) 0.6069(2) 0.33993(16) 0.0493(5) Uani 1 1 d . . . . .
H17 H 0.820381 0.665205 0.362471 0.059 Uiso 1 1 calc R U . . .
C18 C 0.66720(18) 0.60878(19) 0.39000(15) 0.0429(5) Uani 1 1 d . . . . .
H18 H 0.680809 0.667795 0.443998 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 C1 1.352(2) . ?
O1 H1 0.82 . ?
O2 C3 1.361(2) . ?
O2 H2A 0.82 . ?
N1 C11 1.325(2) . ?
N1 C7 1.329(3) . ?
N2 C17 1.322(3) . ?
N2 C16 1.325(3) . ?
C1 C2 1.382(3) . ?
C1 C6 1.389(2) . ?
C2 C3 1.382(3) . ?
C2 H2 0.93 . ?
C3 C4 1.385(3) . ?
C4 C5 1.370(3) . ?
C4 H4 0.93 . ?
C5 C6 1.371(3) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.372(3) . ?
C7 H7 0.93 . ?
C8 C9 1.382(2) . ?
C8 H8 0.93 . ?
C9 C10 1.375(3) . ?
C9 C12 1.498(2) . ?
C10 C11 1.373(2) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 C13 1.541(2) . ?
C12 C13 1.591(2) 3_666 ?
C12 H12 0.98 . ?
C13 C14 1.502(2) . ?
C13 H13 0.98 . ?
C14 C18 1.373(2) . ?
C14 C15 1.376(2) . ?
C15 C16 1.372(3) . ?
C15 H15 0.93 . ?
C16 H16 0.93 . ?
C17 C18 1.379(2) . ?
C17 H17 0.93 . ?
C18 H18 0.93 . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 115.91(17) . . ?
C17 N2 C16 115.75(16) . . ?
O1 C1 C2 122.70(16) . . ?
O1 C1 C6 117.29(18) . . ?
C2 C1 C6 120.01(19) . . ?
C1 C2 C3 119.78(17) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
O2 C3 C2 122.49(17) . . ?
O2 C3 C4 117.24(18) . . ?
C2 C3 C4 120.3(2) . . ?
C5 C4 C3 119.1(2) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.60(18) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 119.2(2) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
N1 C7 C8 123.84(18) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 119.88(19) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 116.31(17) . . ?
C10 C9 C12 123.20(15) . . ?
C8 C9 C12 120.23(17) . . ?
C11 C10 C9 119.90(18) . . ?
C11 C10 H10 120 . . ?
C9 C10 H10 120 . . ?
N1 C11 C10 124.1(2) . . ?
N1 C11 H11 118 . . ?
C10 C11 H11 118 . . ?
C9 C12 C13 118.61(15) . . ?
C9 C12 C13 114.95(13) . 3_666 ?
C13 C12 C13 90.36(12) . 3_666 ?
C9 C12 H12 110.5 . . ?
C13 C12 H12 110.5 . . ?
C13 C12 H12 110.5 3_666 . ?
C14 C13 C12 119.87(14) . . ?
C14 C13 C12 115.10(13) . 3_666 ?
C12 C13 C12 89.64(12) . 3_666 ?
C14 C13 H13 110.2 . . ?
C12 C13 H13 110.2 . . ?
C12 C13 H13 110.2 3_666 . ?
C18 C14 C15 116.22(16) . . ?
C18 C14 C13 124.18(16) . . ?
C15 C14 C13 119.37(16) . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
N2 C16 C15 123.82(19) . . ?
N2 C16 H16 118.1 . . ?
C15 C16 H16 118.1 . . ?
N2 C17 C18 124.2(2) . . ?
N2 C17 H17 117.9 . . ?
C18 C17 H17 117.9 . . ?
C14 C18 C17 119.63(18) . . ?
C14 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.82 1.91 2.721(2) 172.5 3_566
O2 H2A N2 0.82 1.98 2.789(2) 171.3 1_455


_exptl_crystal_recrystallization_method Photoreaction
####################################################################### 
# 
# 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_1_230K
_database_code_depnum_ccdc_archive 'CCDC 1859280'
_audit_update_record             
;
2018-07-30 deposited with the CCDC.
2018-09-14 downloaded from the CCDC.
;

_audit_creation_date             2018-05-21T15:58:04-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C36 H32 N4 O4'
_chemical_formula_weight         584.65

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.3216(8)
_cell_length_b                   9.7698(4)
_cell_length_c                   14.2672(10)
_cell_angle_alpha                90
_cell_angle_beta                 111.713(3)
_cell_angle_gamma                90
_cell_volume                     1466.12(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    1588
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      26.40

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

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.355
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.169
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_F_000             616

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

_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.7806
_shelx_estimated_absorpt_T_min   0.97
_shelx_estimated_absorpt_T_max   0.985

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

_diffrn_ambient_temperature      230(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_number            7748
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.977
_diffrn_reflns_theta_max         27.515
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             3372
_reflns_number_gt                2135
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0455P)²+0.2269P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3372
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1174
_refine_ls_wR_factor_gt          0.0978
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.044

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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 0 '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 0.006 '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 0.09049(13) 0.15015(14) 0.47776(10) 0.0458(4) Uani 1 1 d . . . . .
H1 H 0.025029 0.175126 0.486158 0.069 Uiso 1 1 calc R U . . .
O2 O -0.06157(14) 0.46632(15) 0.20051(11) 0.0551(4) Uani 1 1 d . . . . .
H2A H -0.118904 0.477793 0.222871 0.083 Uiso 1 1 calc R U . . .
N1 N 0.11415(16) 0.77832(16) 0.47702(12) 0.0401(4) Uani 1 1 d . . . . .
N2 N 0.73749(16) 0.52807(16) 0.26155(12) 0.0415(4) Uani 1 1 d . . . . .
C1 C 0.09783(17) 0.21380(18) 0.39569(14) 0.0341(4) Uani 1 1 d . . . . .
C2 C 0.00872(17) 0.30870(17) 0.33987(13) 0.0326(4) Uani 1 1 d . . . . .
H2 H -0.060856 0.330496 0.358005 0.039 Uiso 1 1 calc R U . . .
C3 C 0.02206(18) 0.37144(19) 0.25745(14) 0.0373(4) Uani 1 1 d . . . . .
C4 C 0.12458(19) 0.3391(2) 0.23024(15) 0.0436(5) Uani 1 1 d . . . . .
H4 H 0.133906 0.381377 0.174209 0.052 Uiso 1 1 calc R U . . .
C5 C 0.21219(19) 0.2444(2) 0.28617(16) 0.0449(5) Uani 1 1 d . . . . .
H5 H 0.281302 0.222025 0.267609 0.054 Uiso 1 1 calc R U . . .
C6 C 0.20072(18) 0.1817(2) 0.36893(16) 0.0417(5) Uani 1 1 d . . . . .
H6 H 0.261881 0.117942 0.406878 0.05 Uiso 1 1 calc R U . . .
C7 C 0.2241(2) 0.84408(19) 0.52232(15) 0.0423(5) Uani 1 1 d . . . . .
H7 H 0.222648 0.928359 0.55365 0.051 Uiso 1 1 calc R U . . .
C8 C 0.33937(18) 0.79499(17) 0.52552(14) 0.0363(4) Uani 1 1 d . . . . .
H8 H 0.414063 0.845278 0.558551 0.044 Uiso 1 1 calc R U . . .
C9 C 0.34520(16) 0.67146(16) 0.48006(12) 0.0271(4) Uani 1 1 d . . . . .
C10 C 0.23113(17) 0.60567(19) 0.43075(14) 0.0375(4) Uani 1 1 d . . . . .
H10 H 0.22925 0.52293 0.396601 0.045 Uiso 1 1 calc R U . . .
C11 C 0.12032(18) 0.6617(2) 0.43179(16) 0.0437(5) Uani 1 1 d . . . . .
H11 H 0.044071 0.614176 0.398282 0.052 Uiso 1 1 calc R U . . .
C12 C 0.47171(15) 0.60902(16) 0.49405(12) 0.0272(4) Uani 1 1 d . . . . .
H12 H 0.536216 0.681238 0.50258 0.033 Uiso 1 1 calc R U . . .
C13 C 0.47808(16) 0.50050(16) 0.41743(12) 0.0264(4) Uani 1 1 d . . . . .
H13 H 0.391321 0.476159 0.370842 0.032 Uiso 1 1 calc R U . . .
C14 C 0.56349(15) 0.52325(16) 0.35935(12) 0.0277(4) Uani 1 1 d . . . . .
C15 C 0.54572(18) 0.44606(19) 0.27419(14) 0.0385(5) Uani 1 1 d . . . . .
H15 H 0.473591 0.389854 0.247363 0.046 Uiso 1 1 calc R U . . .
C16 C 0.6337(2) 0.4513(2) 0.22841(15) 0.0455(5) Uani 1 1 d . . . . .
H16 H 0.619193 0.397478 0.170592 0.055 Uiso 1 1 calc R U . . .
C17 C 0.75042(19) 0.6077(2) 0.33958(15) 0.0421(5) Uani 1 1 d . . . . .
H17 H 0.820888 0.666836 0.36237 0.051 Uiso 1 1 calc R U . . .
C18 C 0.66686(17) 0.60967(19) 0.38978(14) 0.0371(4) Uani 1 1 d . . . . .
H18 H 0.68051 0.669598 0.444346 0.045 Uiso 1 1 calc R U . . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.355(2) . ?
O1 H1 0.83 . ?
O2 C3 1.359(2) . ?
O2 H2A 0.83 . ?
N1 C11 1.324(2) . ?
N1 C7 1.336(3) . ?
N2 C17 1.321(2) . ?
N2 C16 1.326(2) . ?
C1 C2 1.385(2) . ?
C1 C6 1.389(2) . ?
C2 C3 1.383(2) . ?
C2 H2 0.94 . ?
C3 C4 1.390(2) . ?
C4 C5 1.375(3) . ?
C4 H4 0.94 . ?
C5 C6 1.378(3) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.375(3) . ?
C7 H7 0.94 . ?
C8 C9 1.383(2) . ?
C8 H8 0.94 . ?
C9 C10 1.380(2) . ?
C9 C12 1.501(2) . ?
C10 C11 1.374(2) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.544(2) . ?
C12 C13 1.591(2) 3_666 ?
C12 H12 0.99 . ?
C13 C14 1.505(2) . ?
C13 H13 0.99 . ?
C14 C18 1.377(2) . ?
C14 C15 1.380(2) . ?
C15 C16 1.379(2) . ?
C15 H15 0.94 . ?
C16 H16 0.94 . ?
C17 C18 1.382(2) . ?
C17 H17 0.94 . ?
C18 H18 0.94 . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 116.22(16) . . ?
C17 N2 C16 116.17(15) . . ?
O1 C1 C2 122.66(15) . . ?
O1 C1 C6 117.36(17) . . ?
C2 C1 C6 119.97(18) . . ?
C3 C2 C1 120.02(16) . . ?
C3 C2 H2 120 . . ?
C1 C2 H2 120 . . ?
O2 C3 C2 122.65(16) . . ?
O2 C3 C4 117.23(17) . . ?
C2 C3 C4 120.12(18) . . ?
C5 C4 C3 119.26(18) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.31(17) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 119.31(19) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
N1 C7 C8 123.46(17) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 119.88(18) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 116.58(16) . . ?
C10 C9 C12 123.08(15) . . ?
C8 C9 C12 120.07(16) . . ?
C11 C10 C9 119.69(17) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
N1 C11 C10 124.12(19) . . ?
N1 C11 H11 117.9 . . ?
C10 C11 H11 117.9 . . ?
C9 C12 C13 118.51(14) . . ?
C9 C12 C13 114.96(13) . 3_666 ?
C13 C12 C13 90.21(12) . 3_666 ?
C9 C12 H12 110.5 . . ?
C13 C12 H12 110.5 . . ?
C13 C12 H12 110.5 3_666 . ?
C14 C13 C12 119.76(14) . . ?
C14 C13 C12 115.01(13) . 3_666 ?
C12 C13 C12 89.79(12) . 3_666 ?
C14 C13 H13 110.2 . . ?
C12 C13 H13 110.2 . . ?
C12 C13 H13 110.2 3_666 . ?
C18 C14 C15 116.28(15) . . ?
C18 C14 C13 124.16(15) . . ?
C15 C14 C13 119.35(15) . . ?
C16 C15 C14 120.08(18) . . ?
C16 C15 H15 120 . . ?
C14 C15 H15 120 . . ?
N2 C16 C15 123.53(18) . . ?
N2 C16 H16 118.2 . . ?
C15 C16 H16 118.2 . . ?
N2 C17 C18 124.13(19) . . ?
N2 C17 H17 117.9 . . ?
C18 C17 H17 117.9 . . ?
C14 C18 C17 119.56(17) . . ?
C14 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.83 1.89 2.7164(19) 172.2 3_566
O2 H2A N2 0.83 1.96 2.7863(19) 171.4 1_455


_exptl_crystal_recrystallization_method Photoreaction
####################################################################### 
# 
# 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_1_250K
_database_code_depnum_ccdc_archive 'CCDC 1859281'
_audit_update_record             
;
2018-07-30 deposited with the CCDC.
2018-09-14 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT906_1_250K              
;
PROBLEM: Large K Value in the Analysis of Variance ......      4.059 Check 
RESPONSE: At this temperature the diffraction was weaker at high angles.
;
# end Validation Reply Form

_audit_creation_date             2018-05-21T15:59:34-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C36 H32 N4 O4'
_chemical_formula_weight         584.65

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.3139(9)
_cell_length_b                   9.7762(5)
_cell_length_c                   14.2685(12)
_cell_angle_alpha                90
_cell_angle_beta                 111.658(4)
_cell_angle_gamma                90
_cell_volume                     1466.78(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    1504
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      26.40

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

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.355
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.169
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_F_000             616

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

_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.7806
_shelx_estimated_absorpt_T_min   0.97
_shelx_estimated_absorpt_T_max   0.985

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

_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_number            7762
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.978
_diffrn_reflns_theta_max         27.529
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             3383
_reflns_number_gt                2088
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0494P)²+0.1072P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3383
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1213
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.042

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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 0 '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 0.006 '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 0.09025(14) 0.14989(14) 0.47747(11) 0.0500(4) Uani 1 1 d . . . . .
H1 H 0.026722 0.177814 0.487611 0.075 Uiso 1 1 calc R U . . .
O2 O -0.06063(15) 0.46609(16) 0.20117(12) 0.0603(4) Uani 1 1 d . . . . .
H2A H -0.118343 0.477122 0.223242 0.09 Uiso 1 1 calc R U . . .
N1 N 0.11477(16) 0.77880(16) 0.47729(12) 0.0444(4) Uani 1 1 d . . . . .
N2 N 0.73796(17) 0.52794(16) 0.26177(13) 0.0450(4) Uani 1 1 d . . . . .
C1 C 0.09786(17) 0.21357(18) 0.39594(14) 0.0370(4) Uani 1 1 d . . . . .
C2 C 0.00921(17) 0.30879(17) 0.34025(14) 0.0355(4) Uani 1 1 d . . . . .
H2 H -0.060325 0.331071 0.358389 0.043 Uiso 1 1 calc R U . . .
C3 C 0.02299(18) 0.37096(19) 0.25809(15) 0.0408(5) Uani 1 1 d . . . . .
C4 C 0.12525(19) 0.3385(2) 0.23089(16) 0.0464(5) Uani 1 1 d . . . . .
H4 H 0.134664 0.380703 0.174841 0.056 Uiso 1 1 calc R U . . .
C5 C 0.21255(19) 0.2442(2) 0.28678(16) 0.0483(5) Uani 1 1 d . . . . .
H5 H 0.281797 0.221847 0.268289 0.058 Uiso 1 1 calc R U . . .
C6 C 0.20106(18) 0.1816(2) 0.36902(16) 0.0453(5) Uani 1 1 d . . . . .
H6 H 0.262223 0.117776 0.406846 0.054 Uiso 1 1 calc R U . . .
C7 C 0.2246(2) 0.84381(19) 0.52234(15) 0.0452(5) Uani 1 1 d . . . . .
H7 H 0.223327 0.92807 0.553681 0.054 Uiso 1 1 calc R U . . .
C8 C 0.33971(19) 0.79458(17) 0.52555(15) 0.0397(5) Uani 1 1 d . . . . .
H8 H 0.414451 0.844686 0.558724 0.048 Uiso 1 1 calc R U . . .
C9 C 0.34568(16) 0.67149(16) 0.48007(13) 0.0293(4) Uani 1 1 d . . . . .
C10 C 0.23150(17) 0.60624(19) 0.43088(15) 0.0408(5) Uani 1 1 d . . . . .
H10 H 0.229476 0.523512 0.396749 0.049 Uiso 1 1 calc R U . . .
C11 C 0.12074(19) 0.6623(2) 0.43184(16) 0.0476(5) Uani 1 1 d . . . . .
H11 H 0.044378 0.615167 0.398139 0.057 Uiso 1 1 calc R U . . .
C12 C 0.47171(16) 0.60882(16) 0.49412(13) 0.0293(4) Uani 1 1 d . . . . .
H12 H 0.536389 0.680863 0.502778 0.035 Uiso 1 1 calc R U . . .
C13 C 0.47830(16) 0.50058(16) 0.41747(13) 0.0285(4) Uani 1 1 d . . . . .
H13 H 0.391556 0.47626 0.370882 0.034 Uiso 1 1 calc R U . . .
C14 C 0.56369(15) 0.52309(16) 0.35951(12) 0.0292(4) Uani 1 1 d . . . . .
C15 C 0.54648(19) 0.44611(19) 0.27463(14) 0.0421(5) Uani 1 1 d . . . . .
H15 H 0.474479 0.389719 0.247938 0.051 Uiso 1 1 calc R U . . .
C16 C 0.6337(2) 0.4512(2) 0.22880(15) 0.0492(5) Uani 1 1 d . . . . .
H16 H 0.619 0.397505 0.170933 0.059 Uiso 1 1 calc R U . . .
C17 C 0.75026(19) 0.6072(2) 0.33991(16) 0.0452(5) Uani 1 1 d . . . . .
H17 H 0.820683 0.66637 0.362881 0.054 Uiso 1 1 calc R U . . .
C18 C 0.66680(17) 0.60905(18) 0.38991(15) 0.0402(5) Uani 1 1 d . . . . .
H18 H 0.680428 0.668816 0.44452 0.048 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 C1 1.350(2) . ?
O1 H1 0.83 . ?
O2 C3 1.361(2) . ?
O2 H2A 0.83 . ?
N1 C11 1.324(2) . ?
N1 C7 1.331(3) . ?
N2 C17 1.323(2) . ?
N2 C16 1.329(3) . ?
C1 C2 1.384(2) . ?
C1 C6 1.393(2) . ?
C2 C3 1.379(2) . ?
C2 H2 0.94 . ?
C3 C4 1.386(2) . ?
C4 C5 1.372(3) . ?
C4 H4 0.94 . ?
C5 C6 1.371(3) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.373(3) . ?
C7 H7 0.94 . ?
C8 C9 1.381(2) . ?
C8 H8 0.94 . ?
C9 C10 1.378(2) . ?
C9 C12 1.496(2) . ?
C10 C11 1.373(2) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.543(2) . ?
C12 C13 1.590(2) 3_666 ?
C12 H12 0.99 . ?
C13 C14 1.502(2) . ?
C13 H13 0.99 . ?
C14 C18 1.372(2) . ?
C14 C15 1.377(2) . ?
C15 C16 1.372(3) . ?
C15 H15 0.94 . ?
C16 H16 0.94 . ?
C17 C18 1.378(2) . ?
C17 H17 0.94 . ?
C18 H18 0.94 . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 116.09(16) . . ?
C17 N2 C16 115.66(15) . . ?
O1 C1 C2 122.81(16) . . ?
O1 C1 C6 117.43(18) . . ?
C2 C1 C6 119.76(18) . . ?
C3 C2 C1 119.93(16) . . ?
C3 C2 H2 120 . . ?
C1 C2 H2 120 . . ?
O2 C3 C2 122.44(16) . . ?
O2 C3 C4 117.22(17) . . ?
C2 C3 C4 120.34(19) . . ?
C5 C4 C3 119.16(19) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C6 C5 C4 121.48(18) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 119.3(2) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
N1 C7 C8 123.62(18) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C9 120.01(19) . . ?
C7 C8 H8 120 . . ?
C9 C8 H8 120 . . ?
C10 C9 C8 116.33(16) . . ?
C10 C9 C12 123.14(15) . . ?
C8 C9 C12 120.23(16) . . ?
C11 C10 C9 119.85(17) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
N1 C11 C10 124.06(19) . . ?
N1 C11 H11 118 . . ?
C10 C11 H11 118 . . ?
C9 C12 C13 118.61(14) . . ?
C9 C12 C13 115.09(13) . 3_666 ?
C13 C12 C13 90.29(12) . 3_666 ?
C9 C12 H12 110.5 . . ?
C13 C12 H12 110.5 . . ?
C13 C12 H12 110.5 3_666 . ?
C14 C13 C12 119.93(14) . . ?
C14 C13 C12 115.00(13) . 3_666 ?
C12 C13 C12 89.71(12) . 3_666 ?
C14 C13 H13 110.2 . . ?
C12 C13 H13 110.2 . . ?
C12 C13 H13 110.2 3_666 . ?
C18 C14 C15 116.14(16) . . ?
C18 C14 C13 124.09(15) . . ?
C15 C14 C13 119.55(16) . . ?
C16 C15 C14 120.42(19) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
N2 C16 C15 123.55(18) . . ?
N2 C16 H16 118.2 . . ?
C15 C16 H16 118.2 . . ?
N2 C17 C18 124.41(19) . . ?
N2 C17 H17 117.8 . . ?
C18 C17 H17 117.8 . . ?
C14 C18 C17 119.59(18) . . ?
C14 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.83 1.89 2.7182(19) 172.3 3_566
O2 H2A N2 0.83 1.96 2.786(2) 171.2 1_455


_exptl_crystal_recrystallization_method Photoreaction
####################################################################### 
# 
# 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_1_290K
_database_code_depnum_ccdc_archive 'CCDC 1859283'
_audit_update_record             
;
2018-07-30 deposited with the CCDC.
2018-09-14 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT026_1_290K              
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        48% Check 
RESPONSE: The diffraction quality was reduced at high angles.
;
# end Validation Reply Form

_audit_creation_date             2018-05-21T16:00:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C36 H32 N4 O4'
_chemical_formula_weight         584.65

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.3117(10)
_cell_length_b                   9.8022(5)
_cell_length_c                   14.2920(13)
_cell_angle_alpha                90
_cell_angle_beta                 111.539(4)
_cell_angle_gamma                90
_cell_volume                     1474.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    1362
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      26.38

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

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.355
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.169
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             616

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

_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.7806
_shelx_estimated_absorpt_T_min   0.97
_shelx_estimated_absorpt_T_max   0.985

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

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0901
_diffrn_reflns_number            7800
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.979
_diffrn_reflns_theta_max         27.556
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_coverage         0
_reflns_number_total             3395
_reflns_number_gt                1634
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0279P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3395
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.106
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.0877
_refine_ls_wR_factor_gt          0.0737
_refine_ls_goodness_of_fit_ref   0.8
_refine_ls_restrained_S_all      0.8
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.036

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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 0 '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 0.006 '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 0.09000(13) 0.14977(13) 0.47727(10) 0.0588(4) Uani 1 1 d . . . . .
H1 H 0.025902 0.175206 0.486227 0.088 Uiso 1 1 calc R U . . .
O2 O -0.05932(14) 0.46601(15) 0.20239(11) 0.0712(4) Uani 1 1 d . . . . .
H2A H -0.116897 0.476103 0.2237 0.107 Uiso 1 1 calc R U . . .
N1 N 0.11529(16) 0.77906(16) 0.47742(12) 0.0513(4) Uani 1 1 d . . . . .
N2 N 0.73864(16) 0.52729(16) 0.26223(12) 0.0528(4) Uani 1 1 d . . . . .
C1 C 0.09767(17) 0.21365(17) 0.39588(14) 0.0427(5) Uani 1 1 d . . . . .
C2 C 0.00981(17) 0.30842(16) 0.34069(13) 0.0415(5) Uani 1 1 d . . . . .
H2 H -0.05901 0.330441 0.358631 0.05 Uiso 1 1 calc R U . . .
C3 C 0.02385(18) 0.37068(18) 0.25882(15) 0.0476(5) Uani 1 1 d . . . . .
C4 C 0.12602(19) 0.33856(19) 0.23202(15) 0.0554(6) Uani 1 1 d . . . . .
H4 H 0.135751 0.380511 0.176921 0.067 Uiso 1 1 calc R U . . .
C5 C 0.21302(19) 0.2441(2) 0.28753(16) 0.0580(6) Uani 1 1 d . . . . .
H5 H 0.281738 0.222226 0.269415 0.07 Uiso 1 1 calc R U . . .
C6 C 0.20069(18) 0.18112(18) 0.36935(16) 0.0529(5) Uani 1 1 d . . . . .
H6 H 0.260569 0.117535 0.406485 0.063 Uiso 1 1 calc R U . . .
C7 C 0.2250(2) 0.84325(18) 0.52246(15) 0.0538(6) Uani 1 1 d . . . . .
H7 H 0.223692 0.926337 0.55349 0.065 Uiso 1 1 calc R U . . .
C8 C 0.34051(18) 0.79398(15) 0.52589(14) 0.0455(5) Uani 1 1 d . . . . .
H8 H 0.414479 0.843197 0.55878 0.055 Uiso 1 1 calc R U . . .
C9 C 0.34610(16) 0.67133(15) 0.48034(12) 0.0339(4) Uani 1 1 d . . . . .
C10 C 0.23190(17) 0.60747(17) 0.43071(14) 0.0472(5) Uani 1 1 d . . . . .
H10 H 0.229561 0.526363 0.396313 0.057 Uiso 1 1 calc R U . . .
C11 C 0.12116(18) 0.66372(18) 0.43202(15) 0.0547(5) Uani 1 1 d . . . . .
H11 H 0.04558 0.617383 0.398735 0.066 Uiso 1 1 calc R U . . .
C12 C 0.47172(15) 0.60832(15) 0.49407(12) 0.0343(4) Uani 1 1 d . . . . .
H12 H 0.535865 0.679308 0.502658 0.041 Uiso 1 1 calc R U . . .
C13 C 0.47862(15) 0.50050(14) 0.41759(12) 0.0331(4) Uani 1 1 d . . . . .
H13 H 0.392883 0.476416 0.371584 0.04 Uiso 1 1 calc R U . . .
C14 C 0.56383(15) 0.52284(15) 0.36009(12) 0.0334(4) Uani 1 1 d . . . . .
C15 C 0.54696(18) 0.44617(17) 0.27529(14) 0.0495(5) Uani 1 1 d . . . . .
H15 H 0.475698 0.390716 0.248636 0.059 Uiso 1 1 calc R U . . .
C16 C 0.6349(2) 0.45136(19) 0.23004(15) 0.0569(6) Uani 1 1 d . . . . .
H16 H 0.620647 0.398035 0.173104 0.068 Uiso 1 1 calc R U . . .
C17 C 0.75059(18) 0.60634(18) 0.34011(16) 0.0534(5) Uani 1 1 d . . . . .
H17 H 0.820293 0.664553 0.362897 0.064 Uiso 1 1 calc R U . . .
C18 C 0.66682(17) 0.60835(17) 0.38980(14) 0.0474(5) Uani 1 1 d . . . . .
H18 H 0.680158 0.667706 0.443478 0.057 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 C1 1.352(2) . ?
O1 H1 0.82 . ?
O2 C3 1.361(2) . ?
O2 H2A 0.82 . ?
N1 C11 1.317(2) . ?
N1 C7 1.328(2) . ?
N2 C16 1.321(2) . ?
N2 C17 1.322(2) . ?
C1 C2 1.377(2) . ?
C1 C6 1.388(2) . ?
C2 C3 1.380(2) . ?
C2 H2 0.93 . ?
C3 C4 1.381(2) . ?
C4 C5 1.372(3) . ?
C4 H4 0.93 . ?
C5 C6 1.374(3) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.377(2) . ?
C7 H7 0.93 . ?
C8 C9 1.380(2) . ?
C8 H8 0.93 . ?
C9 C10 1.375(2) . ?
C9 C12 1.495(2) . ?
C10 C11 1.375(2) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 C13 1.543(2) . ?
C12 C13 1.590(2) 3_666 ?
C12 H12 0.98 . ?
C13 C14 1.495(2) . ?
C13 H13 0.98 . ?
C14 C18 1.370(2) . ?
C14 C15 1.379(2) . ?
C15 C16 1.373(2) . ?
C15 H15 0.93 . ?
C16 H16 0.93 . ?
C17 C18 1.377(2) . ?
C17 H17 0.93 . ?
C18 H18 0.93 . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 116.00(16) . . ?
C16 N2 C17 115.25(16) . . ?
O1 C1 C2 122.99(16) . . ?
O1 C1 C6 117.01(17) . . ?
C2 C1 C6 120.00(18) . . ?
C1 C2 C3 120.03(17) . . ?
C1 C2 H2 120 . . ?
C3 C2 H2 120 . . ?
O2 C3 C2 122.46(16) . . ?
O2 C3 C4 117.33(18) . . ?
C2 C3 C4 120.21(19) . . ?
C5 C4 C3 119.29(19) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.33(18) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 119.14(19) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
N1 C7 C8 123.83(17) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 119.74(18) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 116.30(16) . . ?
C10 C9 C12 123.18(14) . . ?
C8 C9 C12 120.27(16) . . ?
C11 C10 C9 119.89(17) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
N1 C11 C10 124.18(18) . . ?
N1 C11 H11 117.9 . . ?
C10 C11 H11 117.9 . . ?
C9 C12 C13 118.88(14) . . ?
C9 C12 C13 115.04(12) . 3_666 ?
C13 C12 C13 90.46(11) . 3_666 ?
C9 C12 H12 110.3 . . ?
C13 C12 H12 110.3 . . ?
C13 C12 H12 110.3 3_666 . ?
C14 C13 C12 119.98(13) . . ?
C14 C13 C12 115.07(13) . 3_666 ?
C12 C13 C12 89.54(11) . 3_666 ?
C14 C13 H13 110.2 . . ?
C12 C13 H13 110.2 . . ?
C12 C13 H13 110.2 3_666 . ?
C18 C14 C15 115.69(15) . . ?
C18 C14 C13 124.47(15) . . ?
C15 C14 C13 119.64(15) . . ?
C16 C15 C14 120.25(18) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
N2 C16 C15 124.16(18) . . ?
N2 C16 H16 117.9 . . ?
C15 C16 H16 117.9 . . ?
N2 C17 C18 124.45(19) . . ?
N2 C17 H17 117.8 . . ?
C18 C17 H17 117.8 . . ?
C14 C18 C17 119.95(17) . . ?
C14 C18 H18 120 . . ?
C17 C18 H18 120 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.82 1.91 2.7207(18) 172.6 3_566
O2 H2A N2 0.82 1.97 2.7839(19) 170.9 1_455




# END of CIF
_exptl_crystal_recrystallization_method Photoreaction
