# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_bs748
_database_code_depnum_ccdc_archive 'CCDC 2019020'
loop_
_audit_author_name
_audit_author_address
'Oksana Danylyuk'
;Institute of Physical Chemistry, Polish Academy of Sciences
Poland
;
_audit_update_record             
;
2020-07-25 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        BS748
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H41 N3 O4'
_chemical_formula_weight         603.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   28.1693(2)
_cell_length_b                   7.8436(4)
_cell_length_c                   28.7267(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.9300(10)
_cell_angle_gamma                90
_cell_volume                     6252.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    57909
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      70.00

_exptl_crystal_description       plate
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             2576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.663
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.255
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100.0(1)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova (Cu) X-ray Source'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.29
_diffrn_reflns_number            145868
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         5.854
_diffrn_reflns_theta_max         68.251
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             11425
_reflns_number_gt                10704
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0468P)²+5.4747P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         11425
_refine_ls_number_parameters     815
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1326
_refine_ls_wR_factor_gt          0.1303
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_restrained_S_all      1.147
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.56738(5) 0.45985(18) 0.18488(5) 0.0303(3) Uani 1 1 d . . . . .
O4 O 0.63793(6) 0.5469(2) 0.21933(6) 0.0426(4) Uani 1 1 d . . . . .
N3 N 0.60236(6) 0.4550(2) 0.21708(6) 0.0295(4) Uani 1 1 d . . . . .
O2 O 0.50053(5) 0.10522(19) 0.12999(5) 0.0297(3) Uani 1 1 d . . . . .
O1 O 0.55386(5) 0.37881(19) -0.05136(5) 0.0309(3) Uani 1 1 d . . . . .
N2 N 0.57654(6) 0.17138(19) 0.12031(5) 0.0210(3) Uani 1 1 d . . . . .
N1 N 0.48018(6) 0.2903(2) -0.04146(5) 0.0231(3) Uani 1 1 d . . . . .
C8 C 0.52913(7) 0.3184(2) -0.02451(6) 0.0231(4) Uani 1 1 d . . . . .
C15 C 0.58063(7) 0.0725(2) 0.20648(6) 0.0222(4) Uani 1 1 d . . . . .
C24 C 0.59986(7) 0.3395(3) 0.25696(7) 0.0264(4) Uani 1 1 d . . . . .
C32 C 0.63137(7) 0.3768(2) 0.02229(7) 0.0249(4) Uani 1 1 d . . . . .
H32A H 0.6569 0.4234 0.0470 0.030 Uiso 1 1 calc R U . . .
H32B H 0.6168 0.4735 0.0028 0.030 Uiso 1 1 calc R U . . .
C4 C 0.44795(7) 0.2166(2) -0.01584(6) 0.0222(4) Uani 1 1 d . . . . .
C16 C 0.56233(7) -0.0905(2) 0.20444(7) 0.0250(4) Uani 1 1 d . . . . .
H16 H 0.5582 -0.1508 0.1753 0.030 Uiso 1 1 calc R U . . .
C12 C 0.60087(7) 0.1415(2) 0.16609(6) 0.0228(4) Uani 1 1 d . . . . .
C6 C 0.51093(7) 0.1971(2) 0.05271(6) 0.0207(4) Uani 1 1 d . . . . .
C10 C 0.60878(7) 0.2421(2) 0.09360(7) 0.0227(4) Uani 1 1 d . . . . .
C13 C 0.64792(7) 0.1886(3) 0.16745(7) 0.0267(4) Uani 1 1 d . . . . .
H13 H 0.6729 0.1799 0.1942 0.032 Uiso 1 1 calc R U . . .
C38 C 0.75192(7) 0.3112(3) -0.08926(7) 0.0319(5) Uani 1 1 d . . . . .
H38A H 0.7438 0.4299 -0.0993 0.038 Uiso 1 1 calc R U . . .
H38B H 0.7803 0.3157 -0.0636 0.038 Uiso 1 1 calc R U . . .
C19 C 0.57595(7) 0.0786(3) 0.29124(6) 0.0250(4) Uani 1 1 d . . . . .
C14 C 0.65320(7) 0.2521(3) 0.12261(7) 0.0273(4) Uani 1 1 d . . . . .
H14 H 0.6821 0.2940 0.1140 0.033 Uiso 1 1 calc R U . . .
C25 C 0.42360(7) 0.1059(2) 0.05691(7) 0.0237(4) Uani 1 1 d . . . . .
H25A H 0.4363 0.0113 0.0783 0.028 Uiso 1 1 calc R U . . .
H25B H 0.3974 0.0597 0.0328 0.028 Uiso 1 1 calc R U . . .
C9 C 0.52682(7) 0.1537(2) 0.10334(6) 0.0219(4) Uani 1 1 d . . . . .
C18 C 0.55716(7) -0.0891(3) 0.28705(7) 0.0264(4) Uani 1 1 d . . . . .
H18 H 0.5498 -0.1456 0.3142 0.032 Uiso 1 1 calc R U . . .
C2 C 0.40984(8) 0.2767(3) -0.09012(7) 0.0300(4) Uani 1 1 d . . . . .
H2 H 0.3855 0.2866 -0.1173 0.036 Uiso 1 1 calc R U . . .
C5 C 0.46324(7) 0.1717(2) 0.03271(6) 0.0213(4) Uani 1 1 d . . . . .
C20 C 0.58567(6) 0.1651(2) 0.24989(6) 0.0223(4) Uani 1 1 d . . . . .
C11 C 0.59321(7) 0.2945(2) 0.04578(6) 0.0221(4) Uani 1 1 d . . . . .
C17 C 0.54953(7) -0.1703(3) 0.24443(7) 0.0273(4) Uani 1 1 d . . . . .
H17 H 0.5356 -0.2809 0.2417 0.033 Uiso 1 1 calc R U . . .
C27 C 0.35894(7) 0.1861(3) 0.10567(7) 0.0270(4) Uani 1 1 d . . . . .
H27A H 0.3307 0.1813 0.0799 0.032 Uiso 1 1 calc R U . . .
H27B H 0.3647 0.0697 0.1188 0.032 Uiso 1 1 calc R U . . .
C26 C 0.40288(7) 0.2439(2) 0.08555(7) 0.0253(4) Uani 1 1 d . . . . .
H26A H 0.4283 0.2802 0.1119 0.030 Uiso 1 1 calc R U . . .
H26B H 0.3939 0.3442 0.0650 0.030 Uiso 1 1 calc R U . . .
C1 C 0.45653(8) 0.3273(3) -0.08656(7) 0.0284(4) Uani 1 1 d . . . . .
H1 H 0.4705 0.3791 -0.1109 0.034 Uiso 1 1 calc R U . . .
C23 C 0.60740(8) 0.4175(3) 0.30016(7) 0.0336(5) Uani 1 1 d . . . . .
H23 H 0.6180 0.5326 0.3031 0.040 Uiso 1 1 calc R U . . .
C37 C 0.70999(8) 0.2361(3) -0.06964(8) 0.0319(5) Uani 1 1 d . . . . .
H37A H 0.7189 0.1198 -0.0578 0.038 Uiso 1 1 calc R U . . .
H37B H 0.6821 0.2255 -0.0957 0.038 Uiso 1 1 calc R U . . .
C7 C 0.54574(7) 0.2690(2) 0.02534(6) 0.0211(4) Uani 1 1 d . . . . .
C28 C 0.34787(7) 0.3049(3) 0.14423(7) 0.0309(4) Uani 1 1 d . . . . .
H28A H 0.3427 0.4209 0.1308 0.037 Uiso 1 1 calc R U . . .
H28B H 0.3766 0.3095 0.1695 0.037 Uiso 1 1 calc R U . . .
C21 C 0.58373(7) 0.1623(3) 0.33582(7) 0.0308(5) Uani 1 1 d . . . . .
H21 H 0.5779 0.1024 0.3630 0.037 Uiso 1 1 calc R U . . .
C34 C 0.65443(7) 0.2548(3) -0.00903(7) 0.0276(4) Uani 1 1 d . . . . .
H34A H 0.6676 0.1548 0.0100 0.033 Uiso 1 1 calc R U . . .
H34B H 0.6293 0.2133 -0.0350 0.033 Uiso 1 1 calc R U . . .
C3 C 0.40403(7) 0.2065(3) -0.04586(7) 0.0265(4) Uani 1 1 d . . . . .
H3 H 0.3751 0.1607 -0.0382 0.032 Uiso 1 1 calc R U . . .
C30 C 0.30028(8) 0.3669(3) 0.20955(8) 0.0338(5) Uani 1 1 d . . . . .
H30A H 0.3295 0.3497 0.2337 0.041 Uiso 1 1 calc R U . . .
H30B H 0.2993 0.4884 0.2001 0.041 Uiso 1 1 calc R U . . .
C22 C 0.59945(8) 0.3265(3) 0.34028(7) 0.0354(5) Uani 1 1 d . . . . .
H22 H 0.6050 0.3796 0.3705 0.042 Uiso 1 1 calc R U . . .
C35 C 0.69453(7) 0.3389(3) -0.02991(7) 0.0290(4) Uani 1 1 d . . . . .
H35A H 0.7228 0.3555 -0.0045 0.035 Uiso 1 1 calc R U . . .
H35B H 0.6836 0.4528 -0.0421 0.035 Uiso 1 1 calc R U . . .
C29 C 0.30438(8) 0.2579(3) 0.16662(7) 0.0321(5) Uani 1 1 d . . . . .
H29A H 0.2747 0.2714 0.1428 0.039 Uiso 1 1 calc R U . . .
H29B H 0.3069 0.1365 0.1762 0.039 Uiso 1 1 calc R U . . .
C41 C 0.80806(8) 0.2915(4) -0.14843(8) 0.0424(6) Uani 1 1 d . . . . .
H41A H 0.8006 0.4095 -0.1583 0.064 Uiso 1 1 calc R U . . .
H41B H 0.8148 0.2251 -0.1754 0.064 Uiso 1 1 calc R U . . .
H41C H 0.8363 0.2897 -0.1232 0.064 Uiso 1 1 calc R U . . .
C40 C 0.76568(9) 0.2152(3) -0.13050(9) 0.0409(5) Uani 1 1 d . . . . .
H40A H 0.7734 0.0959 -0.1208 0.049 Uiso 1 1 calc R U . . .
H40B H 0.7377 0.2130 -0.1566 0.049 Uiso 1 1 calc R U . . .
C31 C 0.25622(8) 0.3281(3) 0.23157(8) 0.0389(5) Uani 1 1 d . . . . .
H31A H 0.2270 0.3538 0.2088 0.058 Uiso 1 1 calc R U . . .
H31B H 0.2569 0.3982 0.2599 0.058 Uiso 1 1 calc R U . . .
H31C H 0.2563 0.2072 0.2402 0.058 Uiso 1 1 calc R U . . .
O1A O 0.57694(5) 0.15964(17) 0.45462(4) 0.0252(3) Uani 1 1 d . . . . .
N1A N 0.49799(6) 0.18300(19) 0.45959(5) 0.0220(3) Uani 1 1 d . . . . .
N2A N 0.57523(5) 0.3722(2) 0.62250(5) 0.0213(3) Uani 1 1 d . . . . .
O3A O 0.55739(6) 0.09158(18) 0.68385(5) 0.0332(3) Uani 1 1 d . . . . .
O2A O 0.49559(5) 0.4055(2) 0.62455(5) 0.0336(3) Uani 1 1 d . . . . .
C7A C 0.55667(7) 0.2546(2) 0.52853(6) 0.0206(4) Uani 1 1 d . . . . .
N3A N 0.58822(6) 0.0993(2) 0.71973(6) 0.0302(4) Uani 1 1 d . . . . .
C10A C 0.61236(7) 0.3076(2) 0.60085(7) 0.0229(4) Uani 1 1 d . . . . .
C4A C 0.46044(7) 0.2474(2) 0.48028(6) 0.0215(4) Uani 1 1 d . . . . .
C3A C 0.41852(7) 0.2203(2) 0.44851(6) 0.0250(4) Uani 1 1 d . . . . .
H3A H 0.3870 0.2520 0.4527 0.030 Uiso 1 1 calc R U . . .
C2A C 0.43088(7) 0.1367(2) 0.40842(7) 0.0265(4) Uani 1 1 d . . . . .
H2A H 0.4090 0.1007 0.3813 0.032 Uiso 1 1 calc R U . . .
C11A C 0.60308(7) 0.2468(2) 0.55336(6) 0.0213(4) Uani 1 1 d . . . . .
C16A C 0.55037(7) 0.6449(2) 0.70043(7) 0.0252(4) Uani 1 1 d . . . . .
H16A H 0.5513 0.7043 0.6718 0.030 Uiso 1 1 calc R U . . .
O4A O 0.62439(6) 0.0100(2) 0.72699(6) 0.0440(4) Uani 1 1 d . . . . .
C14A C 0.65401(7) 0.3112(3) 0.63375(7) 0.0261(4) Uani 1 1 d . . . . .
H14A H 0.6851 0.2762 0.6288 0.031 Uiso 1 1 calc R U . . .
C8A C 0.54676(7) 0.1960(2) 0.47911(6) 0.0221(4) Uani 1 1 d . . . . .
C29A C 0.32278(7) 0.1985(3) 0.64142(7) 0.0286(4) Uani 1 1 d . . . . .
H29C H 0.3112 0.3153 0.6462 0.034 Uiso 1 1 calc R U . . .
H29D H 0.3574 0.1934 0.6555 0.034 Uiso 1 1 calc R U . . .
C24A C 0.57927(7) 0.2162(2) 0.75746(7) 0.0247(4) Uani 1 1 d . . . . .
C12A C 0.59397(7) 0.4107(2) 0.66936(6) 0.0227(4) Uani 1 1 d . . . . .
C9A C 0.52631(7) 0.3694(2) 0.60133(6) 0.0235(4) Uani 1 1 d . . . . .
C19A C 0.54854(7) 0.4771(2) 0.78548(6) 0.0229(4) Uani 1 1 d . . . . .
C17A C 0.53192(7) 0.7279(2) 0.73658(7) 0.0250(4) Uani 1 1 d . . . . .
H17A H 0.5196 0.8406 0.7319 0.030 Uiso 1 1 calc R U . . .
C15A C 0.56722(6) 0.4806(2) 0.70504(6) 0.0214(4) Uani 1 1 d . . . . .
C6A C 0.51674(7) 0.3162(2) 0.55097(6) 0.0207(4) Uani 1 1 d . . . . .
C18A C 0.53161(7) 0.6467(2) 0.77860(7) 0.0244(4) Uani 1 1 d . . . . .
H18A H 0.5199 0.7045 0.8034 0.029 Uiso 1 1 calc R U . . .
C32A C 0.64634(7) 0.1714(2) 0.53611(7) 0.0236(4) Uani 1 1 d . . . . .
H32C H 0.6351 0.0788 0.5135 0.028 Uiso 1 1 calc R U . . .
H32D H 0.6679 0.1198 0.5633 0.028 Uiso 1 1 calc R U . . .
C20A C 0.56507(7) 0.3891(2) 0.74757(6) 0.0212(4) Uani 1 1 d . . . . .
C21A C 0.54989(7) 0.3961(3) 0.82966(7) 0.0285(4) Uani 1 1 d . . . . .
H21A H 0.5391 0.4566 0.8545 0.034 Uiso 1 1 calc R U . . .
C5A C 0.47009(7) 0.3189(2) 0.52685(6) 0.0208(4) Uani 1 1 d . . . . .
C33A C 0.67556(7) 0.2992(2) 0.51212(7) 0.0252(4) Uani 1 1 d . . . . .
H33A H 0.6582 0.3242 0.4799 0.030 Uiso 1 1 calc R U . . .
H33B H 0.6789 0.4072 0.5302 0.030 Uiso 1 1 calc R U . . .
C26A C 0.39919(7) 0.2531(2) 0.56886(7) 0.0247(4) Uani 1 1 d . . . . .
H26C H 0.4045 0.1388 0.5560 0.030 Uiso 1 1 calc R U . . .
H26D H 0.4127 0.2524 0.6030 0.030 Uiso 1 1 calc R U . . .
C1A C 0.47968(7) 0.1170(2) 0.41562(6) 0.0247(4) Uani 1 1 d . . . . .
H1A H 0.4978 0.0669 0.3942 0.030 Uiso 1 1 calc R U . . .
C13A C 0.64230(7) 0.3764(3) 0.67619(7) 0.0265(4) Uani 1 1 d . . . . .
H13A H 0.6644 0.3937 0.7048 0.032 Uiso 1 1 calc R U . . .
C34A C 0.72553(7) 0.2287(3) 0.50929(7) 0.0291(4) Uani 1 1 d . . . . .
H34C H 0.7220 0.1116 0.4963 0.035 Uiso 1 1 calc R U . . .
H34D H 0.7444 0.2214 0.5417 0.035 Uiso 1 1 calc R U . . .
C23A C 0.58050(8) 0.1408(3) 0.80039(7) 0.0325(5) Uani 1 1 d . . . . .
H23A H 0.5909 0.0260 0.8052 0.039 Uiso 1 1 calc R U . . .
C28A C 0.31729(7) 0.1639(3) 0.58873(7) 0.0293(4) Uani 1 1 d . . . . .
H28C H 0.2827 0.1694 0.5747 0.035 Uiso 1 1 calc R U . . .
H28D H 0.3286 0.0466 0.5841 0.035 Uiso 1 1 calc R U . . .
C27A C 0.34503(7) 0.2885(3) 0.56223(7) 0.0282(4) Uani 1 1 d . . . . .
H27C H 0.3315 0.2830 0.5281 0.034 Uiso 1 1 calc R U . . .
H27D H 0.3400 0.4057 0.5732 0.034 Uiso 1 1 calc R U . . .
C25A C 0.42602(7) 0.3872(2) 0.54401(6) 0.0222(4) Uani 1 1 d . . . . .
H25C H 0.4035 0.4338 0.5167 0.027 Uiso 1 1 calc R U . . .
H25D H 0.4359 0.4823 0.5662 0.027 Uiso 1 1 calc R U . . .
C22A C 0.56623(8) 0.2338(3) 0.83738(7) 0.0339(5) Uani 1 1 d . . . . .
H22A H 0.5680 0.1835 0.8677 0.041 Uiso 1 1 calc R U . . .
C36A C 0.74097(7) 0.2974(3) 0.42619(7) 0.0301(4) Uani 1 1 d . . . . .
H36A H 0.7056 0.3076 0.4163 0.036 Uiso 1 1 calc R U . . .
H36B H 0.7501 0.1782 0.4206 0.036 Uiso 1 1 calc R U . . .
C35A C 0.75389(7) 0.3357(3) 0.47870(7) 0.0312(5) Uani 1 1 d . . . . .
H35C H 0.7478 0.4579 0.4839 0.037 Uiso 1 1 calc R U . . .
H35D H 0.7888 0.3147 0.4891 0.037 Uiso 1 1 calc R U . . .
C30A C 0.29520(8) 0.0729(3) 0.66718(7) 0.0328(5) Uani 1 1 d . . . . .
H30C H 0.2611 0.0704 0.6512 0.039 Uiso 1 1 calc R U . . .
H30D H 0.3087 -0.0426 0.6648 0.039 Uiso 1 1 calc R U . . .
C37A C 0.76576(8) 0.4156(3) 0.39582(7) 0.0328(5) Uani 1 1 d . . . . .
H37C H 0.8010 0.4094 0.4067 0.039 Uiso 1 1 calc R U . . .
H37D H 0.7555 0.5343 0.4004 0.039 Uiso 1 1 calc R U . . .
C38A C 0.75478(10) 0.3732(3) 0.34330(8) 0.0450(6) Uani 1 1 d . . . . .
H38C H 0.7684 0.2614 0.3379 0.067 Uiso 1 1 calc R U . . .
H38D H 0.7691 0.4601 0.3255 0.067 Uiso 1 1 calc R U . . .
H38E H 0.7198 0.3707 0.3327 0.067 Uiso 1 1 calc R U . . .
C31A C 0.29700(9) 0.1160(3) 0.71909(8) 0.0439(6) Uani 1 1 d . . . . .
H31D H 0.3306 0.1156 0.7354 0.066 Uiso 1 1 calc R U . . .
H31E H 0.2786 0.0310 0.7335 0.066 Uiso 1 1 calc R U . . .
H31F H 0.2830 0.2292 0.7218 0.066 Uiso 1 1 calc R U . . .


_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
O3 N3 1.230(2) . ?
O4 N3 1.227(2) . ?
N3 C24 1.472(3) . ?
O2 C9 1.214(2) . ?
O1 C8 1.221(2) . ?
N2 C12 1.394(2) . ?
N2 C10 1.401(2) . ?
N2 C9 1.408(2) . ?
N1 C1 1.382(2) . ?
N1 C4 1.390(2) . ?
N1 C8 1.398(3) . ?
C8 C7 1.480(3) . ?
C15 C16 1.376(3) . ?
C15 C20 1.429(3) . ?
C15 C12 1.481(3) . ?
C24 C23 1.367(3) . ?
C24 C20 1.430(3) . ?
C32 C11 1.509(3) . ?
C32 C34 1.533(3) . ?
C4 C3 1.383(3) . ?
C4 C5 1.431(3) . ?
C16 C17 1.409(3) . ?
C12 C13 1.370(3) . ?
C6 C5 1.382(3) . ?
C6 C7 1.471(3) . ?
C6 C9 1.486(2) . ?
C10 C14 1.381(3) . ?
C10 C11 1.428(3) . ?
C13 C14 1.413(3) . ?
C38 C40 1.510(3) . ?
C38 C37 1.513(3) . ?
C19 C18 1.415(3) . ?
C19 C21 1.422(3) . ?
C19 C20 1.435(3) . ?
C25 C5 1.505(3) . ?
C25 C26 1.534(3) . ?
C18 C17 1.364(3) . ?
C2 C1 1.361(3) . ?
C2 C3 1.421(3) . ?
C11 C7 1.379(3) . ?
C27 C28 1.520(3) . ?
C27 C26 1.523(3) . ?
C23 C22 1.406(3) . ?
C37 C35 1.521(3) . ?
C28 C29 1.524(3) . ?
C21 C22 1.361(3) . ?
C34 C35 1.518(3) . ?
C30 C31 1.518(3) . ?
C30 C29 1.521(3) . ?
C41 C40 1.504(3) . ?
O1A C8A 1.227(2) . ?
N1A C1A 1.380(2) . ?
N1A C4A 1.394(2) . ?
N1A C8A 1.395(2) . ?
N2A C12A 1.392(2) . ?
N2A C10A 1.400(2) . ?
N2A C9A 1.407(2) . ?
O3A N3A 1.229(2) . ?
O2A C9A 1.214(2) . ?
C7A C11A 1.379(3) . ?
C7A C6A 1.471(2) . ?
C7A C8A 1.473(3) . ?
N3A O4A 1.224(2) . ?
N3A C24A 1.474(2) . ?
C10A C14A 1.374(3) . ?
C10A C11A 1.426(3) . ?
C4A C3A 1.379(3) . ?
C4A C5A 1.433(3) . ?
C3A C2A 1.420(3) . ?
C2A C1A 1.363(3) . ?
C11A C32A 1.513(2) . ?
C16A C15A 1.372(3) . ?
C16A C17A 1.400(3) . ?
C14A C13A 1.412(3) . ?
C29A C28A 1.519(3) . ?
C29A C30A 1.523(3) . ?
C24A C23A 1.363(3) . ?
C24A C20A 1.428(3) . ?
C12A C13A 1.368(3) . ?
C12A C15A 1.478(2) . ?
C9A C6A 1.485(3) . ?
C19A C21A 1.414(3) . ?
C19A C18A 1.416(3) . ?
C19A C20A 1.433(3) . ?
C17A C18A 1.366(3) . ?
C15A C20A 1.427(2) . ?
C6A C5A 1.376(3) . ?
C32A C33A 1.534(2) . ?
C21A C22A 1.358(3) . ?
C5A C25A 1.511(2) . ?
C33A C34A 1.528(3) . ?
C26A C27A 1.530(3) . ?
C26A C25A 1.540(3) . ?
C34A C35A 1.535(3) . ?
C23A C22A 1.404(3) . ?
C28A C27A 1.533(3) . ?
C36A C35A 1.519(3) . ?
C36A C37A 1.523(3) . ?
C30A C31A 1.521(3) . ?
C37A C38A 1.524(3) . ?

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
O4 N3 O3 124.23(18) . . ?
O4 N3 C24 117.96(17) . . ?
O3 N3 C24 117.68(16) . . ?
C12 N2 C10 108.87(15) . . ?
C12 N2 C9 127.43(15) . . ?
C10 N2 C9 123.35(15) . . ?
C1 N1 C4 109.30(16) . . ?
C1 N1 C8 125.49(16) . . ?
C4 N1 C8 125.19(15) . . ?
O1 C8 N1 118.49(17) . . ?
O1 C8 C7 126.41(18) . . ?
N1 C8 C7 115.09(16) . . ?
C16 C15 C20 119.31(17) . . ?
C16 C15 C12 119.89(17) . . ?
C20 C15 C12 120.29(17) . . ?
C23 C24 C20 123.57(19) . . ?
C23 C24 N3 114.24(18) . . ?
C20 C24 N3 121.88(17) . . ?
C11 C32 C34 113.68(15) . . ?
C3 C4 N1 106.83(16) . . ?
C3 C4 C5 132.87(18) . . ?
N1 C4 C5 120.27(17) . . ?
C15 C16 C17 121.66(18) . . ?
C13 C12 N2 107.31(16) . . ?
C13 C12 C15 125.28(17) . . ?
N2 C12 C15 127.41(17) . . ?
C5 C6 C7 121.53(16) . . ?
C5 C6 C9 118.77(16) . . ?
C7 C6 C9 119.69(16) . . ?
C14 C10 N2 107.32(16) . . ?
C14 C10 C11 131.31(18) . . ?
N2 C10 C11 121.34(17) . . ?
C12 C13 C14 108.80(17) . . ?
C40 C38 C37 114.86(18) . . ?
C18 C19 C21 120.19(18) . . ?
C18 C19 C20 119.40(17) . . ?
C21 C19 C20 120.39(18) . . ?
C10 C14 C13 107.67(17) . . ?
C5 C25 C26 112.77(15) . . ?
O2 C9 N2 119.40(16) . . ?
O2 C9 C6 125.14(17) . . ?
N2 C9 C6 115.46(15) . . ?
C17 C18 C19 120.61(18) . . ?
C1 C2 C3 107.75(18) . . ?
C6 C5 C4 118.54(17) . . ?
C6 C5 C25 127.09(16) . . ?
C4 C5 C25 114.33(16) . . ?
C15 C20 C24 126.41(17) . . ?
C15 C20 C19 118.56(17) . . ?
C24 C20 C19 115.03(17) . . ?
C7 C11 C10 118.82(17) . . ?
C7 C11 C32 125.79(17) . . ?
C10 C11 C32 115.39(17) . . ?
C18 C17 C16 120.11(18) . . ?
C28 C27 C26 112.11(16) . . ?
C27 C26 C25 113.77(16) . . ?
C2 C1 N1 108.22(17) . . ?
C24 C23 C22 119.7(2) . . ?
C38 C37 C35 114.57(17) . . ?
C11 C7 C6 120.99(16) . . ?
C11 C7 C8 119.71(17) . . ?
C6 C7 C8 119.28(17) . . ?
C27 C28 C29 116.11(17) . . ?
C22 C21 C19 121.26(19) . . ?
C35 C34 C32 112.32(16) . . ?
C4 C3 C2 107.90(18) . . ?
C31 C30 C29 114.00(18) . . ?
C21 C22 C23 119.88(19) . . ?
C34 C35 C37 113.24(17) . . ?
C30 C29 C28 112.66(17) . . ?
C41 C40 C38 113.4(2) . . ?
C1A N1A C4A 109.54(16) . . ?
C1A N1A C8A 125.60(16) . . ?
C4A N1A C8A 124.68(15) . . ?
C12A N2A C10A 108.68(15) . . ?
C12A N2A C9A 126.95(15) . . ?
C10A N2A C9A 123.58(15) . . ?
C11A C7A C6A 121.11(16) . . ?
C11A C7A C8A 119.35(16) . . ?
C6A C7A C8A 119.52(16) . . ?
O4A N3A O3A 124.16(18) . . ?
O4A N3A C24A 118.26(17) . . ?
O3A N3A C24A 117.47(16) . . ?
C14A C10A N2A 107.55(16) . . ?
C14A C10A C11A 131.21(17) . . ?
N2A C10A C11A 121.19(17) . . ?
C3A C4A N1A 106.77(16) . . ?
C3A C4A C5A 132.93(18) . . ?
N1A C4A C5A 120.27(16) . . ?
C4A C3A C2A 107.82(17) . . ?
C1A C2A C3A 108.13(17) . . ?
C7A C11A C10A 118.76(16) . . ?
C7A C11A C32A 126.40(16) . . ?
C10A C11A C32A 114.77(16) . . ?
C15A C16A C17A 122.13(18) . . ?
C10A C14A C13A 107.59(17) . . ?
O1A C8A N1A 118.96(17) . . ?
O1A C8A C7A 126.19(17) . . ?
N1A C8A C7A 114.85(15) . . ?
C28A C29A C30A 113.30(17) . . ?
C23A C24A C20A 123.69(18) . . ?
C23A C24A N3A 114.47(17) . . ?
C20A C24A N3A 121.45(16) . . ?
C13A C12A N2A 107.33(16) . . ?
C13A C12A C15A 125.95(17) . . ?
N2A C12A C15A 126.70(16) . . ?
O2A C9A N2A 119.78(17) . . ?
O2A C9A C6A 125.03(17) . . ?
N2A C9A C6A 115.17(15) . . ?
C21A C19A C18A 120.24(17) . . ?
C21A C19A C20A 120.26(17) . . ?
C18A C19A C20A 119.49(17) . . ?
C18A C17A C16A 119.90(17) . . ?
C16A C15A C20A 119.34(17) . . ?
C16A C15A C12A 119.38(17) . . ?
C20A C15A C12A 120.60(16) . . ?
C5A C6A C7A 121.37(16) . . ?
C5A C6A C9A 118.92(16) . . ?
C7A C6A C9A 119.66(16) . . ?
C17A C18A C19A 120.55(17) . . ?
C11A C32A C33A 114.62(15) . . ?
C15A C20A C24A 126.57(17) . . ?
C15A C20A C19A 118.40(17) . . ?
C24A C20A C19A 115.00(16) . . ?
C22A C21A C19A 121.55(19) . . ?
C6A C5A C4A 118.36(16) . . ?
C6A C5A C25A 127.47(16) . . ?
C4A C5A C25A 114.17(16) . . ?
C34A C33A C32A 110.98(16) . . ?
C27A C26A C25A 112.15(15) . . ?
C2A C1A N1A 107.73(17) . . ?
C12A C13A C14A 108.80(17) . . ?
C33A C34A C35A 114.07(17) . . ?
C24A C23A C22A 119.55(19) . . ?
C29A C28A C27A 114.07(17) . . ?
C26A C27A C28A 113.92(16) . . ?
C5A C25A C26A 113.93(15) . . ?
C21A C22A C23A 119.79(19) . . ?
C35A C36A C37A 113.16(17) . . ?
C36A C35A C34A 113.64(17) . . ?
C31A C30A C29A 113.50(19) . . ?
C36A C37A C38A 113.53(18) . . ?

_refine_diff_density_max         0.284
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform/hexane'
####################################################################### 
# 
# 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_BS591_B_0m
_database_code_depnum_ccdc_archive 'CCDC 2019018'
loop_
_audit_author_name
_audit_author_address
'Maja Morawiak'
;Institute of Organic Chemistry PAS
Poland
;
_audit_update_record             
;
2020-07-25 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
6,12-Diheptyl-3,9-bis(2-methyl-4-nitrophenyl)-5H,11H-dipyrrolo[1,2-b:1',2'-g][2,6]naphthyridine-5,11-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H46 N4 O6'
_chemical_formula_sum            'C42 H46 N4 O6'
_chemical_formula_weight         702.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.8094(2)
_cell_length_b                   12.3555(4)
_cell_length_c                   31.0929(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.544(2)
_cell_angle_gamma                90
_cell_volume                     1844.09(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2335
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      68.67

_exptl_crystal_description       cube
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             748
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.112
_exptl_absorpt_coefficient_mu    0.686
_shelx_estimated_absorpt_T_min   0.867
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8670
_exptl_absorpt_correction_T_max  0.9270
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_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_detector_area_resol_mean ?
_diffrn_reflns_number            36814
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.848
_diffrn_reflns_theta_max         68.675
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3383
_reflns_number_gt                2335
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1593P)²+1.2976P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3383
_refine_ls_number_parameters     257
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0821
_refine_ls_wR_factor_ref         0.2792
_refine_ls_wR_factor_gt          0.2441
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2833(5) 0.4040(2) -0.07476(7) 0.0665(8) Uani 1 1 d . . . . .
O2 O -0.3272(13) 0.8222(4) 0.25138(16) 0.157(2) Uani 1 1 d . . . . .
O3 O -0.5349(10) 0.6872(4) 0.27684(12) 0.1353(17) Uani 1 1 d . . . . .
N1 N 0.0578(5) 0.4713(2) 0.08041(8) 0.0464(7) Uani 1 1 d . . . . .
N2 N -0.3824(10) 0.7284(5) 0.25171(12) 0.0957(13) Uani 1 1 d . . . . .
C1 C 0.0706(7) 0.4574(3) 0.12510(10) 0.0535(8) Uani 1 1 d . . . . .
C2 C 0.2268(9) 0.3669(3) 0.13353(11) 0.0660(10) Uani 1 1 d . . . . .
H2 H 0.2665 0.3372 0.1607 0.079 Uiso 1 1 calc R U . . .
C3 C 0.3179(9) 0.3258(3) 0.09499(11) 0.0639(10) Uani 1 1 d . . . . .
H3 H 0.4298 0.2651 0.0922 0.077 Uiso 1 1 calc R U . . .
C4 C 0.2134(7) 0.3907(2) 0.06194(10) 0.0474(8) Uani 1 1 d . . . . .
C5 C 0.2397(6) 0.3870(2) 0.01646(10) 0.0434(7) Uani 1 1 d . . . . .
C6 C 0.0922(6) 0.4603(2) -0.00924(9) 0.0418(7) Uani 1 1 d . . . . .
C7 C 0.1206(6) 0.4590(2) -0.05624(10) 0.0468(8) Uani 1 1 d . . . . .
C8 C -0.0421(7) 0.5313(3) 0.15689(10) 0.0553(9) Uani 1 1 d . . . . .
C9 C 0.0301(7) 0.6407(3) 0.15989(10) 0.0542(8) Uani 1 1 d . . . . .
C10 C -0.0833(8) 0.7022(3) 0.19211(12) 0.0628(10) Uani 1 1 d . . . . .
C11 C -0.2598(9) 0.6568(4) 0.21956(11) 0.0678(10) Uani 1 1 d . . . . .
C12 C -0.3248(10) 0.5493(4) 0.21873(12) 0.0753(12) Uani 1 1 d . . . . .
C13 C -0.2134(9) 0.4865(3) 0.18719(11) 0.0668(10) Uani 1 1 d . . . . .
C14 C 0.2279(8) 0.6912(3) 0.13127(12) 0.0665(10) Uani 1 1 d . . . . .
H14A H 0.3606 0.6381 0.1231 0.100 Uiso 1 1 calc R U . . .
H14B H 0.3237 0.7495 0.1462 0.100 Uiso 1 1 calc R U . . .
H14C H 0.1275 0.7186 0.1059 0.100 Uiso 1 1 calc R U . . .
C15 C 0.4207(7) 0.2981(3) 0.00063(12) 0.0525(8) Uani 1 1 d . . . . .
C16 C 0.2516(8) 0.2028(3) -0.01744(12) 0.0622(9) Uani 1 1 d . . . . .
H16A H 0.1697 0.1653 0.0061 0.075 Uiso 1 1 calc R U . . .
H16B H 0.1006 0.2299 -0.0366 0.075 Uiso 1 1 calc R U . . .
C17 C 0.4190(13) 0.1241(4) -0.04146(18) 0.1023(18) Uani 1 1 d . . . . .
H17A H 0.5610 0.0931 -0.0216 0.123 Uiso 1 1 calc R U . . .
H17B H 0.5132 0.1630 -0.0634 0.123 Uiso 1 1 calc R U . . .
C18 C 0.253(2) 0.0343(5) -0.0624(3) 0.181(4) Uani 1 1 d D . . . .
H18A H 0.2862 -0.0293 -0.0446 0.218 Uiso 1 1 calc R U . . .
H18B H 0.0585 0.0532 -0.0606 0.218 Uiso 1 1 calc R U . . .
C20 C 0.162(2) -0.0754(8) -0.1278(3) 0.178(4) Uani 1 1 d D . . . .
H20A H 0.0283 -0.1159 -0.1120 0.214 Uiso 1 1 calc R U . . .
H20B H 0.3067 -0.1253 -0.1354 0.214 Uiso 1 1 calc R U . . .
C21 C 0.022(2) -0.0330(8) -0.1671(3) 0.172(3) Uani 1 1 d D . . . .
H21A H -0.1127 0.0202 -0.1599 0.258 Uiso 1 1 calc R U . . .
H21B H -0.0696 -0.0910 -0.1829 0.258 Uiso 1 1 calc R U . . .
H21C H 0.1572 -0.0003 -0.1846 0.258 Uiso 1 1 calc R U . . .
H10 H -0.017(9) 0.777(4) 0.1924(14) 0.091(14) Uiso 1 1 d . . . . .
H13 H -0.226(7) 0.399(3) 0.1893(12) 0.066(10) Uiso 1 1 d . . . . .
H15A H 0.548(7) 0.274(3) 0.0240(11) 0.046(8) Uiso 1 1 d . . . . .
H15B H 0.530(8) 0.323(3) -0.0213(13) 0.064(11) Uiso 1 1 d . . . . .
H12 H -0.473(9) 0.519(4) 0.2391(15) 0.089(13) Uiso 1 1 d . . . . .
C19 C 0.282(3) 0.0052(13) -0.1007(3) 0.279(9) Uani 1 1 d D . . . .
H19A H 0.4800 -0.0082 -0.1014 0.335 Uiso 1 1 calc R U . . .
H19B H 0.2483 0.0712 -0.1171 0.335 Uiso 1 1 calc R U . . .


_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 C7 1.209(4) . ?
O2 N2 1.189(6) . ?
O3 N2 1.216(6) . ?
N1 C4 1.392(4) . ?
N1 C1 1.398(4) . ?
N1 C7 1.401(4) 3_565 ?
N2 C11 1.484(5) . ?
C1 C2 1.364(5) . ?
C1 C8 1.473(5) . ?
C2 C3 1.397(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.428(4) . ?
C5 C6 1.376(4) . ?
C5 C15 1.504(4) . ?
C6 C6 1.463(6) 3_565 ?
C6 C7 1.477(4) . ?
C7 N1 1.401(4) 3_565 ?
C8 C9 1.397(5) . ?
C8 C13 1.403(5) . ?
C9 C10 1.396(5) . ?
C9 C14 1.480(5) . ?
C10 C11 1.362(6) . ?
C10 H10 0.98(5) . ?
C11 C12 1.364(6) . ?
C12 C13 1.385(5) . ?
C12 H12 1.05(5) . ?
C13 H13 1.08(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.518(5) . ?
C15 H15A 0.97(3) . ?
C15 H15B 0.94(4) . ?
C16 C17 1.492(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.493(9) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.259(9) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C20 C19 1.404(10) . ?
C20 C21 1.457(10) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C1 109.3(3) . . ?
C4 N1 C7 123.1(3) . 3_565 ?
C1 N1 C7 126.6(3) . 3_565 ?
O2 N2 O3 123.9(5) . . ?
O2 N2 C11 118.5(4) . . ?
O3 N2 C11 117.6(5) . . ?
C2 C1 N1 106.4(3) . . ?
C2 C1 C8 126.9(3) . . ?
N1 C1 C8 126.5(3) . . ?
C1 C2 C3 109.4(3) . . ?
C1 C2 H2 125.3 . . ?
C3 C2 H2 125.3 . . ?
C4 C3 C2 108.1(3) . . ?
C4 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
C3 C4 N1 106.9(3) . . ?
C3 C4 C5 132.2(3) . . ?
N1 C4 C5 120.9(3) . . ?
C6 C5 C4 118.7(3) . . ?
C6 C5 C15 125.4(3) . . ?
C4 C5 C15 115.8(3) . . ?
C5 C6 C6 121.1(3) . 3_565 ?
C5 C6 C7 119.4(3) . . ?
C6 C6 C7 119.5(3) 3_565 . ?
O1 C7 N1 118.9(3) . 3_565 ?
O1 C7 C6 125.5(3) . . ?
N1 C7 C6 115.7(3) 3_565 . ?
C9 C8 C13 119.4(3) . . ?
C9 C8 C1 123.0(3) . . ?
C13 C8 C1 117.5(3) . . ?
C10 C9 C8 118.0(3) . . ?
C10 C9 C14 119.7(3) . . ?
C8 C9 C14 122.3(3) . . ?
C11 C10 C9 120.8(4) . . ?
C11 C10 H10 127(3) . . ?
C9 C10 H10 112(3) . . ?
C10 C11 C12 122.7(4) . . ?
C10 C11 N2 117.7(4) . . ?
C12 C11 N2 119.6(4) . . ?
C11 C12 C13 117.5(4) . . ?
C11 C12 H12 120(2) . . ?
C13 C12 H12 122(3) . . ?
C12 C13 C8 121.5(4) . . ?
C12 C13 H13 119(2) . . ?
C8 C13 H13 118(2) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C15 C16 112.3(3) . . ?
C5 C15 H15A 109.1(19) . . ?
C16 C15 H15A 110.2(19) . . ?
C5 C15 H15B 111(2) . . ?
C16 C15 H15B 107(2) . . ?
H15A C15 H15B 107(3) . . ?
C17 C16 C15 113.4(3) . . ?
C17 C16 H16A 108.9 . . ?
C15 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 C18 114.4(6) . . ?
C16 C17 H17A 108.7 . . ?
C18 C17 H17A 108.7 . . ?
C16 C17 H17B 108.7 . . ?
C18 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C19 C18 C17 122.6(8) . . ?
C19 C18 H18A 106.7 . . ?
C17 C18 H18A 106.7 . . ?
C19 C18 H18B 106.7 . . ?
C17 C18 H18B 106.7 . . ?
H18A C18 H18B 106.6 . . ?
C19 C20 C21 113.5(10) . . ?
C19 C20 H20A 108.9 . . ?
C21 C20 H20A 108.9 . . ?
C19 C20 H20B 108.9 . . ?
C21 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C19 C20 134.8(10) . . ?
C18 C19 H19A 103.5 . . ?
C20 C19 H19A 103.5 . . ?
C18 C19 H19B 103.5 . . ?
C20 C19 H19B 103.5 . . ?
H19A C19 H19B 105.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 -1.7(4) . . . . ?
C7 N1 C1 C2 167.2(3) 3_565 . . . ?
C4 N1 C1 C8 173.6(3) . . . . ?
C7 N1 C1 C8 -17.6(5) 3_565 . . . ?
N1 C1 C2 C3 1.6(4) . . . . ?
C8 C1 C2 C3 -173.6(4) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C3 C4 N1 -0.1(4) . . . . ?
C2 C3 C4 C5 179.9(4) . . . . ?
C1 N1 C4 C3 1.1(4) . . . . ?
C7 N1 C4 C3 -168.3(3) 3_565 . . . ?
C1 N1 C4 C5 -178.9(3) . . . . ?
C7 N1 C4 C5 11.7(4) 3_565 . . . ?
C3 C4 C5 C6 175.5(4) . . . . ?
N1 C4 C5 C6 -4.5(4) . . . . ?
C3 C4 C5 C15 -1.9(5) . . . . ?
N1 C4 C5 C15 178.1(3) . . . . ?
C4 C5 C6 C6 -1.0(5) . . . 3_565 ?
C15 C5 C6 C6 176.1(3) . . . 3_565 ?
C4 C5 C6 C7 178.9(3) . . . . ?
C15 C5 C6 C7 -4.0(5) . . . . ?
C5 C6 C7 O1 -6.7(5) . . . . ?
C6 C6 C7 O1 173.3(4) 3_565 . . . ?
C5 C6 C7 N1 173.7(3) . . . 3_565 ?
C6 C6 C7 N1 -6.3(5) 3_565 . . 3_565 ?
C2 C1 C8 C9 118.7(4) . . . . ?
N1 C1 C8 C9 -55.6(5) . . . . ?
C2 C1 C8 C13 -56.6(5) . . . . ?
N1 C1 C8 C13 129.1(4) . . . . ?
C13 C8 C9 C10 -2.9(5) . . . . ?
C1 C8 C9 C10 -178.1(3) . . . . ?
C13 C8 C9 C14 174.9(3) . . . . ?
C1 C8 C9 C14 -0.2(5) . . . . ?
C8 C9 C10 C11 -0.3(5) . . . . ?
C14 C9 C10 C11 -178.2(4) . . . . ?
C9 C10 C11 C12 3.3(6) . . . . ?
C9 C10 C11 N2 -177.2(3) . . . . ?
O2 N2 C11 C10 1.9(7) . . . . ?
O3 N2 C11 C10 -178.3(4) . . . . ?
O2 N2 C11 C12 -178.6(6) . . . . ?
O3 N2 C11 C12 1.1(7) . . . . ?
C10 C11 C12 C13 -2.8(7) . . . . ?
N2 C11 C12 C13 177.7(4) . . . . ?
C11 C12 C13 C8 -0.6(6) . . . . ?
C9 C8 C13 C12 3.4(6) . . . . ?
C1 C8 C13 C12 178.9(4) . . . . ?
C6 C5 C15 C16 -77.0(4) . . . . ?
C4 C5 C15 C16 100.2(3) . . . . ?
C5 C15 C16 C17 168.1(4) . . . . ?
C15 C16 C17 C18 -175.5(5) . . . . ?
C16 C17 C18 C19 133.8(13) . . . . ?
C17 C18 C19 C20 178.5(15) . . . . ?
C21 C20 C19 C18 121(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
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
C2 H2 O2 0.93 2.74 3.623(6) 159.5 2_545
C2 H2 O3 0.93 2.93 3.793(6) 155.5 2_545
C2 H2 N2 0.93 3.06 3.986(5) 177.0 2_545
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445

_refine_diff_density_max         0.714
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.075

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform/hexane'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2019019'
loop_
_audit_author_name
_audit_author_address
' Trevor D. Lohrey'
;Department of Chemistry, University of California, Berkeley, Latimer Hall, Berkeley, CA, USA 
United States of America
;
_audit_update_record             
;
2020-07-25 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
6,12-Diheptyl-3,9-bis(3-nitrophenyl)-5H,11H-dipyrrolo[1,2-b:1',2'-g][2,6]naphthyridine-5,11-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H42 N4 O6'
_chemical_formula_sum            'C40 H42 N4 O6'
_chemical_formula_weight         674.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 'Calculated using XDISP in WinGX (Farrugia, 1999)'
H H 0.0000 0.0000 'Calculated using XDISP in WinGX (Farrugia, 1999)'
N N 0.0065 0.0035 'Calculated using XDISP in WinGX (Farrugia, 1999)'
O O 0.0115 0.0064 'Calculated using XDISP in WinGX (Farrugia, 1999)'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.2829(4)
_cell_length_b                   27.290(2)
_cell_length_c                   14.9334(13)
_cell_angle_alpha                90
_cell_angle_beta                 91.466(4)
_cell_angle_gamma                90
_cell_volume                     1744.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    26557
_cell_measurement_theta_min      2.073
_cell_measurement_theta_max      28.296

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             716
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.006
_exptl_crystal_size_min          0.002
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6767
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source, station 12.2.1'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_measurement_device_type  'Bruker D8 with PHOTON-II CPAD detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            26557
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.073
_diffrn_reflns_theta_max         28.296
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4022
_reflns_number_gt                2966
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3 Bruker, Madison WI'
_computing_cell_refinement       'SAINT V8.38A Bruker, Madison WI'
_computing_data_reduction        'SAINT V8.38A Bruker, Madison WI'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0874P)²+0.5107P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   diffmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4022
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1615
_refine_ls_wR_factor_gt          0.1482
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4202(4) 0.57024(6) 0.49434(10) 0.0204(4) Uani 1 1 d . . . . .
C2 C 0.6913(4) 0.63015(6) 0.59701(11) 0.0252(4) Uani 1 1 d . . . . .
C3 C 0.5905(4) 0.67613(6) 0.55408(11) 0.0277(4) Uani 1 1 d . . . . .
C4 C 0.6509(5) 0.68563(7) 0.46447(12) 0.0318(4) Uani 1 1 d . . . . .
H4 H 0.7549 0.6622 0.4289 0.038 Uiso 1 1 calc R U . . .
C5 C 0.5559(6) 0.72991(7) 0.42880(13) 0.0385(5) Uani 1 1 d . . . . .
C6 C 0.4016(6) 0.76524(7) 0.47689(15) 0.0425(5) Uani 1 1 d . . . . .
H6 H 0.3339 0.7949 0.4495 0.051 Uiso 1 1 calc R U . . .
C7 C 0.3486(6) 0.75601(7) 0.56615(15) 0.0429(5) Uani 1 1 d . . . . .
H7 H 0.2454 0.7798 0.6013 0.052 Uiso 1 1 calc R U . . .
C8 C 0.4460(5) 0.71214(7) 0.60469(13) 0.0347(5) Uani 1 1 d . . . . .
H8 H 0.4136 0.7066 0.6665 0.042 Uiso 1 1 calc R U . . .
C9 C 0.8765(5) 0.62509(7) 0.67285(11) 0.0300(4) Uani 1 1 d . . . . .
H9 H 0.9479 0.6511 0.7104 0.036 Uiso 1 1 calc R U . . .
C10 C 0.9432(4) 0.57514(7) 0.68591(11) 0.0268(4) Uani 1 1 d . . . . .
H10 H 1.0689 0.5616 0.7330 0.032 Uiso 1 1 calc R U . . .
C11 C 0.7924(4) 0.54923(6) 0.61766(10) 0.0209(4) Uani 1 1 d . . . . .
C12 C 0.7772(4) 0.49812(6) 0.59861(10) 0.0194(3) Uani 1 1 d . . . . .
C13 C 0.5915(4) 0.48247(6) 0.52712(10) 0.0186(3) Uani 1 1 d . . . . .
C14 C 0.9661(4) 0.46573(6) 0.66150(11) 0.0221(4) Uani 1 1 d . . . . .
H14A H 1.1335 0.4856 0.6906 0.027 Uiso 1 1 calc R U . . .
H14B H 1.0670 0.4397 0.6263 0.027 Uiso 1 1 calc R U . . .
C15 C 0.7716(4) 0.44184(6) 0.73402(11) 0.0230(4) Uani 1 1 d . . . . .
H15A H 0.6803 0.4676 0.7719 0.028 Uiso 1 1 calc R U . . .
H15B H 0.5978 0.4231 0.7055 0.028 Uiso 1 1 calc R U . . .
C16 C 0.9699(4) 0.40757(7) 0.79241(12) 0.0278(4) Uani 1 1 d . . . . .
H16A H 1.1533 0.4260 0.8160 0.033 Uiso 1 1 calc R U . . .
H16B H 1.0485 0.3808 0.7543 0.033 Uiso 1 1 calc R U . . .
C17 C 0.8019(5) 0.38484(7) 0.87129(12) 0.0312(4) Uani 1 1 d . . . . .
H17A H 0.6059 0.3695 0.8487 0.037 Uiso 1 1 calc R U . . .
H17B H 0.9350 0.3586 0.8976 0.037 Uiso 1 1 calc R U . . .
C18 C 0.7239(5) 0.42124(8) 0.94458(11) 0.0322(4) Uani 1 1 d . . . . .
H18A H 0.9145 0.4401 0.9608 0.039 Uiso 1 1 calc R U . . .
H18B H 0.5665 0.4447 0.9205 0.039 Uiso 1 1 calc R U . . .
C19 C 0.5989(5) 0.39785(9) 1.02884(13) 0.0459(6) Uani 1 1 d . . . . .
H19A H 0.4098 0.3786 1.0127 0.055 Uiso 1 1 calc R U . . .
H19B H 0.7575 0.3749 1.0537 0.055 Uiso 1 1 calc R U . . .
C20 C 0.5178(6) 0.43480(11) 1.10038(14) 0.0550(7) Uani 1 1 d . . . . .
H20A H 0.7021 0.4548 1.1154 0.082 Uiso 1 1 calc R U . . .
H20B H 0.4503 0.4175 1.1540 0.082 Uiso 1 1 calc R U . . .
H20C H 0.3487 0.4560 1.0780 0.082 Uiso 1 1 calc R U . . .
N1 N 0.6358(3) 0.58332(5) 0.56325(8) 0.0206(3) Uani 1 1 d . . . . .
N2 N 0.6223(6) 0.74005(7) 0.33468(13) 0.0593(6) Uani 1 1 d . . . . .
O1 O 0.2631(3) 0.60189(4) 0.45800(8) 0.0281(3) Uani 1 1 d . . . . .
O2 O 0.5436(7) 0.77949(7) 0.30415(14) 0.0954(9) Uani 1 1 d . . . . .
O3 O 0.7543(6) 0.70916(7) 0.29105(11) 0.0830(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.214(2) . ?
C1 N1 1.411(2) . ?
C1 C13 1.474(2) 3_666 ?
C2 C9 1.373(3) . ?
C2 N1 1.392(2) . ?
C2 C3 1.469(2) . ?
C3 C4 1.394(2) . ?
C3 C8 1.394(3) . ?
C4 C5 1.378(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(3) . ?
C5 N2 1.467(3) . ?
C6 C7 1.381(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.388(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.405(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(2) . ?
C10 H10 0.9500 . ?
C11 N1 1.396(2) . ?
C11 C12 1.425(2) . ?
C12 C13 1.383(2) . ?
C12 C14 1.510(2) . ?
C13 C13 1.467(3) 3_666 ?
C13 C1 1.474(2) 3_666 ?
C14 C15 1.529(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.523(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.527(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.522(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.520(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.516(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N2 O2 1.213(2) . ?
N2 O3 1.214(3) . ?

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 C1 N1 119.39(15) . . ?
O1 C1 C13 125.57(15) . 3_666 ?
N1 C1 C13 115.04(14) . 3_666 ?
C9 C2 N1 107.22(15) . . ?
C9 C2 C3 127.08(16) . . ?
N1 C2 C3 125.51(15) . . ?
C4 C3 C8 119.02(17) . . ?
C4 C3 C2 121.21(16) . . ?
C8 C3 C2 119.68(16) . . ?
C5 C4 C3 118.31(18) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C6 123.49(19) . . ?
C4 C5 N2 118.24(18) . . ?
C6 C5 N2 118.27(18) . . ?
C7 C6 C5 117.87(19) . . ?
C7 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C6 C7 C8 120.17(19) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C3 121.07(17) . . ?
C7 C8 H8 119.5 . . ?
C3 C8 H8 119.5 . . ?
C2 C9 C10 108.85(16) . . ?
C2 C9 H9 125.6 . . ?
C10 C9 H9 125.6 . . ?
C11 C10 C9 107.67(16) . . ?
C11 C10 H10 126.2 . . ?
C9 C10 H10 126.2 . . ?
C10 C11 N1 107.21(15) . . ?
C10 C11 C12 131.62(16) . . ?
N1 C11 C12 121.17(14) . . ?
C13 C12 C11 118.63(15) . . ?
C13 C12 C14 126.02(15) . . ?
C11 C12 C14 115.34(14) . . ?
C12 C13 C13 120.89(19) . 3_666 ?
C12 C13 C1 119.00(14) . 3_666 ?
C13 C13 C1 120.11(18) 3_666 3_666 ?
C12 C14 C15 113.41(14) . . ?
C12 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
C12 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C16 C15 C14 111.19(14) . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C15 C16 C17 115.11(15) . . ?
C15 C16 H16A 108.5 . . ?
C17 C16 H16A 108.5 . . ?
C15 C16 H16B 108.5 . . ?
C17 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C18 C17 C16 113.96(16) . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C16 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 C17 114.19(18) . . ?
C19 C18 H18A 108.7 . . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C20 C19 C18 113.3(2) . . ?
C20 C19 H19A 108.9 . . ?
C18 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
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 . . ?
C2 N1 C11 109.03(13) . . ?
C2 N1 C1 126.80(14) . . ?
C11 N1 C1 123.49(14) . . ?
O2 N2 O3 122.88(19) . . ?
O2 N2 C5 117.94(19) . . ?
O3 N2 C5 119.18(17) . . ?

_refine_diff_density_max         0.238
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.068


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform/hexane'
_exptl_crystal_preparation       Luminescent
