# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_global
_database_code_depnum_ccdc_archive 'CCDC 2168756'
loop_
_audit_author_name
_audit_author_address
'Artur Sikorski'
;University of Gdansk, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2022-04-26 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_journal_coeditor_?tes           
; ?
;
_iucr_compatibility_tag          ACTA95
loop_
_publ_author_foot?te
;
?
;
;
?
;
;
?
;
;
?
;
;
?
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C14 H14 O3), 3(C13 H9 N)'
_chemical_formula_sum            'C67 H55 N3 O6'
_chemical_formula_weight         998.14

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   17.3435(14)
_cell_length_b                   5.9437(6)
_cell_length_c                   25.672(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.975(9)
_cell_angle_gamma                90
_cell_volume                     2588.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    18978
_cell_measurement_theta_min      3.245
_cell_measurement_theta_max      25.00

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             1052
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   
;
CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd.,
2008)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      295(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  'Oxford Diffraction Ruby CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.4002
_diffrn_reflns_number            18978
_diffrn_reflns_av_unetI/netI     0.1194
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.245
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_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 0.869
_diffrn_reflns_point_group_measured_fraction_full 0.869
_reflns_number_total             7896
_reflns_number_gt                3854
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.575
_reflns_Friedel_fraction_max     0.710
_reflns_Friedel_fraction_full    0.710

_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       
'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_cell_refinement       
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0257P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 968 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(10)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         7896
_refine_ls_number_parameters     695
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1578
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.1231
_refine_ls_wR_factor_gt          0.0927
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_restrained_S_all      0.955
_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
C1C C 0.7774(4) -0.1639(15) 0.9027(3) 0.093(2) Uani 1 1 d . . . . .
H1C H 0.757796 -0.297623 0.913607 0.111 Uiso 1 1 calc R U . . .
C1A C 0.7543(4) 0.3741(15) 0.1477(4) 0.097(3) Uani 1 1 d . . . . .
H1A H 0.783955 0.246984 0.159664 0.116 Uiso 1 1 calc R U . . .
C1B C 0.6086(4) 0.5707(13) 0.5380(3) 0.077(2) Uani 1 1 d . . . . .
H1B H 0.585824 0.433293 0.543426 0.092 Uiso 1 1 calc R U . . .
C2C C 0.7619(4) -0.1076(17) 0.8500(4) 0.099(3) Uani 1 1 d . . . . .
H2C H 0.731643 -0.203790 0.825358 0.118 Uiso 1 1 calc R U . . .
C2A C 0.7480(4) 0.4408(17) 0.0964(4) 0.105(3) Uani 1 1 d . . . . .
H2A H 0.772821 0.357778 0.073874 0.125 Uiso 1 1 calc R U . . .
C2B C 0.5794(4) 0.6960(17) 0.4939(3) 0.092(3) Uani 1 1 d . . . . .
H2B H 0.536537 0.641207 0.469201 0.111 Uiso 1 1 calc R U . . .
C3C C 0.7905(5) 0.0907(17) 0.8326(3) 0.098(3) Uani 1 1 d . . . . .
H3C H 0.780633 0.123169 0.796382 0.118 Uiso 1 1 calc R U . . .
C3A C 0.7046(5) 0.6336(19) 0.0768(3) 0.113(3) Uani 1 1 d . . . . .
H3A H 0.701414 0.679237 0.041732 0.136 Uiso 1 1 calc R U . . .
C3B C 0.6115(5) 0.9048(17) 0.4845(3) 0.093(3) Uani 1 1 d . . . . .
H3B H 0.589244 0.986919 0.454270 0.112 Uiso 1 1 calc R U . . .
C4C C 0.8328(4) 0.2380(14) 0.8680(3) 0.083(2) Uani 1 1 d . . . . .
H4C H 0.850213 0.372569 0.855951 0.099 Uiso 1 1 calc R U . . .
C4A C 0.6674(4) 0.7528(16) 0.1094(4) 0.098(3) Uani 1 1 d . . . . .
H4A H 0.637504 0.877832 0.096079 0.118 Uiso 1 1 calc R U . . .
C4B C 0.6744(4) 0.9868(14) 0.5190(3) 0.083(2) Uani 1 1 d . . . . .
H4B H 0.696088 1.124160 0.512269 0.100 Uiso 1 1 calc R U . . .
C5C C 0.9596(4) 0.3948(13) 1.0543(3) 0.078(2) Uani 1 1 d . . . . .
H5C H 0.978604 0.532935 1.045459 0.094 Uiso 1 1 calc R U . . .
C5A C 0.6192(4) 0.8616(13) 0.2893(4) 0.083(2) Uani 1 1 d . . . . .
H5A H 0.590048 0.991576 0.279163 0.100 Uiso 1 1 calc R U . . .
C5B C 0.8648(4) 0.8884(13) 0.6883(3) 0.077(2) Uani 1 1 d . . . . .
H5B H 0.889561 1.024271 0.684387 0.092 Uiso 1 1 calc R U . . .
C6C C 0.9774(4) 0.3234(16) 1.1051(3) 0.095(3) Uani 1 1 d . . . . .
H6C H 1.008556 0.411637 1.131213 0.114 Uiso 1 1 calc R U . . .
C6A C 0.6312(4) 0.7931(15) 0.3404(4) 0.090(3) Uani 1 1 d . . . . .
H6A H 0.610965 0.875578 0.365231 0.108 Uiso 1 1 calc R U . . .
C6B C 0.8904(4) 0.7598(15) 0.7318(3) 0.090(2) Uani 1 1 d . . . . .
H6B H 0.932352 0.808561 0.758087 0.108 Uiso 1 1 calc R U . . .
C7C C 0.9487(5) 0.1160(17) 1.1186(3) 0.093(3) Uani 1 1 d . . . . .
H7C H 0.961459 0.068061 1.153844 0.112 Uiso 1 1 calc R U . . .
C7A C 0.6753(4) 0.5935(16) 0.3560(3) 0.087(2) Uani 1 1 d . . . . .
H7A H 0.683527 0.546829 0.391267 0.104 Uiso 1 1 calc R U . . .
C7B C 0.8539(4) 0.5520(15) 0.7377(3) 0.085(2) Uani 1 1 d . . . . .
H7B H 0.872876 0.464726 0.767681 0.101 Uiso 1 1 calc R U . . .
C8C C 0.9037(4) -0.0149(14) 1.0825(3) 0.081(2) Uani 1 1 d . . . . .
H8C H 0.885162 -0.151056 1.092897 0.098 Uiso 1 1 calc R U . . .
C8A C 0.7054(4) 0.4701(14) 0.3207(3) 0.079(2) Uani 1 1 d . . . . .
H8A H 0.733496 0.339340 0.331693 0.095 Uiso 1 1 calc R U . . .
C8B C 0.7922(4) 0.4767(13) 0.7008(3) 0.0697(19) Uani 1 1 d . . . . .
H8B H 0.769148 0.338981 0.705625 0.084 Uiso 1 1 calc R U . . .
C9C C 0.8939(3) 0.3267(12) 0.9611(3) 0.0668(18) Uani 1 1 d . . . . .
H9C H 0.910894 0.465234 0.950887 0.080 Uiso 1 1 calc R U . . .
C9A C 0.6400(4) 0.8094(13) 0.1985(3) 0.077(2) Uani 1 1 d . . . . .
H9A H 0.610714 0.937903 0.187184 0.093 Uiso 1 1 calc R U . . .
C9B C 0.7710(4) 0.9402(12) 0.6040(3) 0.0662(18) Uani 1 1 d . . . . .
H9B H 0.793882 1.078108 0.599219 0.079 Uiso 1 1 calc R U . . .
N10C N 0.8388(3) -0.0858(10) 0.9920(2) 0.0753(16) Uani 1 1 d . . . . .
N10A N 0.7259(3) 0.4212(10) 0.2334(3) 0.0723(17) Uani 1 1 d D . . . .
N10B N 0.7012(3) 0.5259(9) 0.6192(2) 0.0614(14) Uani 1 1 d . . . . .
C11C C 0.8231(4) -0.0203(12) 0.9408(3) 0.0642(19) Uani 1 1 d . . . . .
C11A C 0.7175(4) 0.4909(14) 0.1828(3) 0.072(2) Uani 1 1 d . . . . .
C11B C 0.6744(4) 0.6534(12) 0.5755(3) 0.0605(18) Uani 1 1 d . . . . .
C12C C 0.8503(4) 0.1861(12) 0.9234(3) 0.0626(18) Uani 1 1 d . . . . .
C12A C 0.6731(4) 0.6907(13) 0.1631(3) 0.073(2) Uani 1 1 d . . . . .
C12B C 0.7078(4) 0.8626(12) 0.5658(3) 0.0621(18) Uani 1 1 d . . . . .
C13C C 0.8836(4) 0.0523(13) 1.0279(3) 0.0681(19) Uani 1 1 d . . . . .
C13A C 0.6940(4) 0.5401(14) 0.2669(3) 0.069(2) Uani 1 1 d . . . . .
C13B C 0.7625(4) 0.6064(11) 0.6552(3) 0.0562(17) Uani 1 1 d . . . . .
C14C C 0.9124(4) 0.2622(12) 1.0139(3) 0.0629(18) Uani 1 1 d . . . . .
C14A C 0.6497(4) 0.7405(13) 0.2511(3) 0.069(2) Uani 1 1 d . . . . .
C14B C 0.7998(4) 0.8156(11) 0.6486(3) 0.0594(18) Uani 1 1 d . . . . .
C21B C 0.5247(3) -0.1470(11) 0.7827(3) 0.0601(17) Uani 1 1 d . . . . .
H21B H 0.495471 -0.015164 0.781419 0.072 Uiso 1 1 calc R U . . .
C21A C 1.0021(3) -0.1289(11) 0.3533(2) 0.0572(16) Uani 1 1 d . . . . .
H21A H 1.011114 0.003579 0.336273 0.069 Uiso 1 1 calc R U . . .
C22B C 0.5548(3) -0.2057(10) 0.7396(2) 0.0519(16) Uani 1 1 d . . . . .
C22A C 0.9461(3) -0.2782(11) 0.3283(2) 0.0535(16) Uani 1 1 d . . . . .
C23B C 0.5989(3) -0.4062(11) 0.7422(2) 0.0606(18) Uani 1 1 d . . . . .
H23B H 0.620178 -0.448745 0.713260 0.073 Uiso 1 1 calc R U . . .
C23A C 0.9335(3) -0.4759(11) 0.3546(2) 0.0610(18) Uani 1 1 d . . . . .
H23A H 0.895308 -0.576840 0.337913 0.073 Uiso 1 1 calc R U . . .
C24B C 0.6107(3) -0.5380(11) 0.7864(2) 0.0612(17) Uani 1 1 d . . . . .
H24B H 0.639284 -0.670579 0.786901 0.073 Uiso 1 1 calc R U . . .
C24A C 0.9756(3) -0.5246(11) 0.4041(2) 0.0585(17) Uani 1 1 d . . . . .
H24A H 0.965628 -0.657757 0.420610 0.070 Uiso 1 1 calc R U . . .
C25B C 0.5947(3) -0.6112(12) 0.8783(3) 0.0670(19) Uani 1 1 d . . . . .
H25B H 0.623909 -0.743024 0.879837 0.080 Uiso 1 1 calc R U . . .
C25A C 1.0795(3) -0.4266(11) 0.4823(2) 0.0550(17) Uani 1 1 d . . . . .
H25A H 1.070475 -0.558979 0.499412 0.066 Uiso 1 1 calc R U . . .
C26B C 0.5658(4) -0.5467(14) 0.9206(3) 0.074(2) Uani 1 1 d . . . . .
C26A C 1.1360(4) -0.2814(12) 0.5065(2) 0.0560(17) Uani 1 1 d . . . . .
C27B C 0.5203(4) -0.3517(15) 0.9190(3) 0.080(2) Uani 1 1 d . . . . .
H27B H 0.500169 -0.310620 0.948471 0.097 Uiso 1 1 calc R U . . .
C27A C 1.1486(3) -0.0786(11) 0.4814(3) 0.0622(18) Uani 1 1 d . . . . .
H27A H 1.187050 0.021031 0.498425 0.075 Uiso 1 1 calc R U . . .
C28B C 0.5052(4) -0.2211(13) 0.8740(3) 0.073(2) Uani 1 1 d . . . . .
H28B H 0.474182 -0.092763 0.872880 0.088 Uiso 1 1 calc R U . . .
C28A C 1.1049(3) -0.0270(11) 0.4325(2) 0.0612(17) Uani 1 1 d . . . . .
H28A H 1.113559 0.108671 0.416643 0.073 Uiso 1 1 calc R U . . .
C29B C 0.5365(3) -0.2807(12) 0.8295(3) 0.0584(17) Uani 1 1 d . . . . .
C29A C 1.0463(3) -0.1763(11) 0.4053(2) 0.0508(16) Uani 1 1 d . . . . .
C30B C 0.5808(3) -0.4795(11) 0.8313(3) 0.0566(17) Uani 1 1 d . . . . .
C30A C 1.0339(3) -0.3770(10) 0.4308(2) 0.0481(15) Uani 1 1 d . . . . .
O31B O 0.5762(3) -0.6561(11) 0.9687(2) 0.1022(18) Uani 1 1 d . . . . .
O31A O 1.1844(2) -0.3133(9) 0.55566(17) 0.0723(13) Uani 1 1 d . . . . .
C32B C 0.6340(5) -0.8339(15) 0.9768(3) 0.114(3) Uani 1 1 d . . . . .
H32D H 0.642432 -0.885199 1.013035 0.171 Uiso 1 1 calc R U . . .
H32E H 0.682731 -0.778289 0.969622 0.171 Uiso 1 1 calc R U . . .
H32F H 0.615466 -0.956603 0.953235 0.171 Uiso 1 1 calc R U . . .
C32A C 1.1742(4) -0.5152(14) 0.5821(2) 0.089(2) Uani 1 1 d . . . . .
H32A H 1.209521 -0.517708 0.616249 0.133 Uiso 1 1 calc R U . . .
H32B H 1.185365 -0.640592 0.561241 0.133 Uiso 1 1 calc R U . . .
H32C H 1.120835 -0.525062 0.586761 0.133 Uiso 1 1 calc R U . . .
C33B C 0.5398(3) -0.0676(11) 0.6894(2) 0.0597(17) Uani 1 1 d . . . . .
H33B H 0.501467 0.047798 0.694148 0.072 Uiso 1 1 calc R U . . .
C33A C 0.8994(4) -0.2439(11) 0.2722(3) 0.0648(19) Uani 1 1 d . . . . .
H33A H 0.852287 -0.338528 0.268172 0.078 Uiso 1 1 calc R U . . .
C34B C 0.6104(4) 0.0549(12) 0.6807(3) 0.0647(19) Uani 1 1 d . . . . .
C34A C 0.8723(5) -0.0108(15) 0.2616(3) 0.075(2) Uani 1 1 d . . . . .
O35B O 0.5957(2) 0.1909(9) 0.63762(18) 0.0784(14) Uani 1 1 d D . . . .
H35B H 0.643(3) 0.273(11) 0.634(3) 0.118 Uiso 1 1 d D U . . .
O35A O 0.8049(3) 0.0386(9) 0.2735(2) 0.1023(18) Uani 1 1 d D . . . .
H35A H 0.783(4) 0.170(8) 0.251(2) 0.153 Uiso 1 1 d D U . . .
O36B O 0.6758(3) 0.0433(8) 0.70829(18) 0.0809(14) Uani 1 1 d . . . . .
O36A O 0.9091(3) 0.1340(10) 0.2427(2) 0.1001(18) Uani 1 1 d . . . . .
C37B C 0.5015(4) -0.2012(13) 0.6400(2) 0.080(2) Uani 1 1 d . . . . .
H37D H 0.488590 -0.101394 0.610036 0.120 Uiso 1 1 calc R U . . .
H37E H 0.454374 -0.272097 0.645930 0.120 Uiso 1 1 calc R U . . .
H37F H 0.537580 -0.314108 0.632882 0.120 Uiso 1 1 calc R U . . .
C37A C 0.9447(4) -0.3220(13) 0.2309(2) 0.092(2) Uani 1 1 d . . . . .
H37A H 0.913882 -0.294563 0.195882 0.137 Uiso 1 1 calc R U . . .
H37B H 0.955493 -0.480079 0.235299 0.137 Uiso 1 1 calc R U . . .
H37C H 0.993517 -0.240758 0.235400 0.137 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
C1C C2C 1.366(9) . ?
C1C C11C 1.410(9) . ?
C1C H1C 0.9300 . ?
C1A C2A 1.358(9) . ?
C1A C11A 1.394(9) . ?
C1A H1A 0.9300 . ?
C1B C2B 1.362(9) . ?
C1B C11B 1.420(8) . ?
C1B H1B 0.9300 . ?
C2C C3C 1.388(11) . ?
C2C H2C 0.9300 . ?
C2A C3A 1.406(11) . ?
C2A H2A 0.9300 . ?
C2B C3B 1.402(11) . ?
C2B H2B 0.9300 . ?
C3C C4C 1.361(10) . ?
C3C H3C 0.9300 . ?
C3A C4A 1.358(10) . ?
C3A H3A 0.9300 . ?
C3B C4B 1.345(9) . ?
C3B H3B 0.9300 . ?
C4C C12C 1.426(8) . ?
C4C H4C 0.9300 . ?
C4A C12A 1.411(9) . ?
C4A H4A 0.9300 . ?
C4B C12B 1.428(8) . ?
C4B H4B 0.9300 . ?
C5C C6C 1.347(9) . ?
C5C C14C 1.419(8) . ?
C5C H5C 0.9300 . ?
C5A C6A 1.346(9) . ?
C5A C14A 1.406(9) . ?
C5A H5A 0.9300 . ?
C5B C6B 1.350(9) . ?
C5B C14B 1.421(8) . ?
C5B H5B 0.9300 . ?
C6C C7C 1.400(11) . ?
C6C H6C 0.9300 . ?
C6A C7A 1.422(10) . ?
C6A H6A 0.9300 . ?
C6B C7B 1.410(10) . ?
C6B H6B 0.9300 . ?
C7C C8C 1.332(9) . ?
C7C H7C 0.9300 . ?
C7A C8A 1.352(9) . ?
C7A H7A 0.9300 . ?
C7B C8B 1.350(8) . ?
C7B H7B 0.9300 . ?
C8C C13C 1.429(8) . ?
C8C H8C 0.9300 . ?
C8A C13A 1.416(9) . ?
C8A H8A 0.9300 . ?
C8B C13B 1.408(8) . ?
C8B H8B 0.9300 . ?
C9C C12C 1.379(8) . ?
C9C C14C 1.382(8) . ?
C9C H9C 0.9300 . ?
C9A C12A 1.367(9) . ?
C9A C14A 1.387(8) . ?
C9A H9A 0.9300 . ?
C9B C14B 1.368(8) . ?
C9B C12B 1.389(8) . ?
C9B H9B 0.9300 . ?
N10C C11C 1.345(7) . ?
N10C C13C 1.352(8) . ?
N10A C13A 1.320(8) . ?
N10A C11A 1.342(8) . ?
N10B C13B 1.344(7) . ?
N10B C11B 1.354(7) . ?
C11C C12C 1.420(9) . ?
C11A C12A 1.448(10) . ?
C11B C12B 1.416(9) . ?
C13C C14C 1.418(9) . ?
C13A C14A 1.430(9) . ?
C13B C14B 1.428(8) . ?
C21B C22B 1.363(7) . ?
C21B C29B 1.418(8) . ?
C21B H21B 0.9300 . ?
C21A C22A 1.373(7) . ?
C21A C29A 1.423(7) . ?
C21A H21A 0.9300 . ?
C22B C23B 1.410(8) . ?
C22B C33B 1.505(7) . ?
C22A C23A 1.396(8) . ?
C22A C33A 1.512(7) . ?
C23B C24B 1.360(8) . ?
C23B H23B 0.9300 . ?
C23A C24A 1.359(7) . ?
C23A H23A 0.9300 . ?
C24B C30B 1.400(7) . ?
C24B H24B 0.9300 . ?
C24A C30A 1.405(7) . ?
C24A H24A 0.9300 . ?
C25B C26B 1.342(9) . ?
C25B C30B 1.416(8) . ?
C25B H25B 0.9300 . ?
C25A C26A 1.356(8) . ?
C25A C30A 1.423(7) . ?
C25A H25A 0.9300 . ?
C26B O31B 1.376(8) . ?
C26B C27B 1.399(10) . ?
C26A O31A 1.377(6) . ?
C26A C27A 1.404(8) . ?
C27B C28B 1.371(9) . ?
C27B H27B 0.9300 . ?
C27A C28A 1.360(7) . ?
C27A H27A 0.9300 . ?
C28B C29B 1.409(8) . ?
C28B H28B 0.9300 . ?
C28A C29A 1.419(8) . ?
C28A H28A 0.9300 . ?
C29B C30B 1.405(8) . ?
C29A C30A 1.398(8) . ?
O31B C32B 1.442(9) . ?
O31A C32A 1.407(8) . ?
C32B H32D 0.9600 . ?
C32B H32E 0.9600 . ?
C32B H32F 0.9600 . ?
C32A H32A 0.9600 . ?
C32A H32B 0.9600 . ?
C32A H32C 0.9600 . ?
C33B C34B 1.482(8) . ?
C33B C37B 1.528(7) . ?
C33B H33B 0.9800 . ?
C33A C34A 1.471(10) . ?
C33A C37A 1.517(8) . ?
C33A H33A 0.9800 . ?
C34B O36B 1.208(6) . ?
C34B O35B 1.350(7) . ?
C34A O36A 1.230(8) . ?
C34A O35A 1.302(8) . ?
O35B H35B 0.99(3) . ?
O35A H35A 1.00(2) . ?
C37B H37D 0.9600 . ?
C37B H37E 0.9600 . ?
C37B H37F 0.9600 . ?
C37A H37A 0.9600 . ?
C37A H37B 0.9600 . ?
C37A H37C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2C C1C C11C 120.3(8) . . ?
C2C C1C H1C 119.8 . . ?
C11C C1C H1C 119.8 . . ?
C2A C1A C11A 121.8(8) . . ?
C2A C1A H1A 119.1 . . ?
C11A C1A H1A 119.1 . . ?
C2B C1B C11B 118.9(8) . . ?
C2B C1B H1B 120.6 . . ?
C11B C1B H1B 120.6 . . ?
C1C C2C C3C 121.1(8) . . ?
C1C C2C H2C 119.4 . . ?
C3C C2C H2C 119.4 . . ?
C1A C2A C3A 120.9(9) . . ?
C1A C2A H2A 119.5 . . ?
C3A C2A H2A 119.5 . . ?
C1B C2B C3B 122.3(8) . . ?
C1B C2B H2B 118.8 . . ?
C3B C2B H2B 118.8 . . ?
C4C C3C C2C 120.7(8) . . ?
C4C C3C H3C 119.7 . . ?
C2C C3C H3C 119.6 . . ?
C4A C3A C2A 119.5(9) . . ?
C4A C3A H3A 120.3 . . ?
C2A C3A H3A 120.3 . . ?
C4B C3B C2B 120.3(8) . . ?
C4B C3B H3B 119.9 . . ?
C2B C3B H3B 119.9 . . ?
C3C C4C C12C 120.0(8) . . ?
C3C C4C H4C 120.0 . . ?
C12C C4C H4C 120.0 . . ?
C3A C4A C12A 121.4(8) . . ?
C3A C4A H4A 119.3 . . ?
C12A C4A H4A 119.3 . . ?
C3B C4B C12B 119.9(8) . . ?
C3B C4B H4B 120.0 . . ?
C12B C4B H4B 120.0 . . ?
C6C C5C C14C 121.0(8) . . ?
C6C C5C H5C 119.5 . . ?
C14C C5C H5C 119.5 . . ?
C6A C5A C14A 121.3(8) . . ?
C6A C5A H5A 119.4 . . ?
C14A C5A H5A 119.4 . . ?
C6B C5B C14B 119.8(7) . . ?
C6B C5B H5B 120.1 . . ?
C14B C5B H5B 120.1 . . ?
C5C C6C C7C 119.7(8) . . ?
C5C C6C H6C 120.1 . . ?
C7C C6C H6C 120.1 . . ?
C5A C6A C7A 119.5(8) . . ?
C5A C6A H6A 120.2 . . ?
C7A C6A H6A 120.2 . . ?
C5B C6B C7B 120.4(7) . . ?
C5B C6B H6B 119.8 . . ?
C7B C6B H6B 119.8 . . ?
C8C C7C C6C 122.0(8) . . ?
C8C C7C H7C 119.0 . . ?
C6C C7C H7C 119.0 . . ?
C8A C7A C6A 121.5(8) . . ?
C8A C7A H7A 119.2 . . ?
C6A C7A H7A 119.2 . . ?
C8B C7B C6B 121.6(7) . . ?
C8B C7B H7B 119.2 . . ?
C6B C7B H7B 119.2 . . ?
C7C C8C C13C 120.5(8) . . ?
C7C C8C H8C 119.7 . . ?
C13C C8C H8C 119.7 . . ?
C7A C8A C13A 119.9(8) . . ?
C7A C8A H8A 120.0 . . ?
C13A C8A H8A 120.0 . . ?
C7B C8B C13B 120.1(7) . . ?
C7B C8B H8B 120.0 . . ?
C13B C8B H8B 120.0 . . ?
C12C C9C C14C 120.1(7) . . ?
C12C C9C H9C 119.9 . . ?
C14C C9C H9C 119.9 . . ?
C12A C9A C14A 120.8(7) . . ?
C12A C9A H9A 119.6 . . ?
C14A C9A H9A 119.6 . . ?
C14B C9B C12B 120.6(7) . . ?
C14B C9B H9B 119.7 . . ?
C12B C9B H9B 119.7 . . ?
C11C N10C C13C 117.5(6) . . ?
C13A N10A C11A 119.3(6) . . ?
C13B N10B C11B 117.2(6) . . ?
N10C C11C C1C 118.2(7) . . ?
N10C C11C C12C 123.0(6) . . ?
C1C C11C C12C 118.7(7) . . ?
N10A C11A C1A 120.0(8) . . ?
N10A C11A C12A 122.3(7) . . ?
C1A C11A C12A 117.7(8) . . ?
N10B C11B C12B 123.7(6) . . ?
N10B C11B C1B 117.3(7) . . ?
C12B C11B C1B 119.0(7) . . ?
C9C C12C C11C 118.2(6) . . ?
C9C C12C C4C 122.8(7) . . ?
C11C C12C C4C 119.0(7) . . ?
C9A C12A C4A 124.1(8) . . ?
C9A C12A C11A 117.3(7) . . ?
C4A C12A C11A 118.7(8) . . ?
C9B C12B C11B 117.3(6) . . ?
C9B C12B C4B 123.1(7) . . ?
C11B C12B C4B 119.6(7) . . ?
N10C C13C C14C 123.0(6) . . ?
N10C C13C C8C 119.1(7) . . ?
C14C C13C C8C 117.9(7) . . ?
N10A C13A C8A 119.1(8) . . ?
N10A C13A C14A 122.3(7) . . ?
C8A C13A C14A 118.6(8) . . ?
N10B C13B C8B 118.5(6) . . ?
N10B C13B C14B 122.9(6) . . ?
C8B C13B C14B 118.7(6) . . ?
C9C C14C C13C 118.1(6) . . ?
C9C C14C C5C 123.0(7) . . ?
C13C C14C C5C 118.9(6) . . ?
C9A C14A C5A 122.8(8) . . ?
C9A C14A C13A 118.1(7) . . ?
C5A C14A C13A 119.1(7) . . ?
C9B C14B C5B 122.2(7) . . ?
C9B C14B C13B 118.3(6) . . ?
C5B C14B C13B 119.4(7) . . ?
C22B C21B C29B 122.0(6) . . ?
C22B C21B H21B 119.0 . . ?
C29B C21B H21B 119.0 . . ?
C22A C21A C29A 120.2(6) . . ?
C22A C21A H21A 119.9 . . ?
C29A C21A H21A 119.9 . . ?
C21B C22B C23B 118.3(6) . . ?
C21B C22B C33B 121.9(6) . . ?
C23B C22B C33B 119.8(6) . . ?
C21A C22A C23A 118.9(5) . . ?
C21A C22A C33A 123.1(6) . . ?
C23A C22A C33A 117.9(6) . . ?
C24B C23B C22B 120.8(6) . . ?
C24B C23B H23B 119.6 . . ?
C22B C23B H23B 119.6 . . ?
C24A C23A C22A 121.7(6) . . ?
C24A C23A H23A 119.2 . . ?
C22A C23A H23A 119.2 . . ?
C23B C24B C30B 121.8(6) . . ?
C23B C24B H24B 119.1 . . ?
C30B C24B H24B 119.1 . . ?
C23A C24A C30A 121.0(6) . . ?
C23A C24A H24A 119.5 . . ?
C30A C24A H24A 119.5 . . ?
C26B C25B C30B 120.4(7) . . ?
C26B C25B H25B 119.8 . . ?
C30B C25B H25B 119.8 . . ?
C26A C25A C30A 120.2(6) . . ?
C26A C25A H25A 119.9 . . ?
C30A C25A H25A 119.9 . . ?
C25B C26B O31B 126.3(8) . . ?
C25B C26B C27B 121.1(7) . . ?
O31B C26B C27B 112.7(8) . . ?
C25A C26A O31A 125.3(6) . . ?
C25A C26A C27A 120.2(6) . . ?
O31A C26A C27A 114.5(6) . . ?
C28B C27B C26B 120.2(7) . . ?
C28B C27B H27B 119.9 . . ?
C26B C27B H27B 119.9 . . ?
C28A C27A C26A 120.4(6) . . ?
C28A C27A H27A 119.8 . . ?
C26A C27A H27A 119.8 . . ?
C27B C28B C29B 120.2(7) . . ?
C27B C28B H28B 119.9 . . ?
C29B C28B H28B 119.9 . . ?
C27A C28A C29A 121.2(6) . . ?
C27A C28A H28A 119.4 . . ?
C29A C28A H28A 119.4 . . ?
C30B C29B C28B 119.0(6) . . ?
C30B C29B C21B 118.8(6) . . ?
C28B C29B C21B 122.2(7) . . ?
C30A C29A C28A 117.9(5) . . ?
C30A C29A C21A 120.1(5) . . ?
C28A C29A C21A 122.0(6) . . ?
C24B C30B C29B 118.3(6) . . ?
C24B C30B C25B 122.5(7) . . ?
C29B C30B C25B 119.2(6) . . ?
C29A C30A C24A 118.1(6) . . ?
C29A C30A C25A 120.1(6) . . ?
C24A C30A C25A 121.9(6) . . ?
C26B O31B C32B 115.7(6) . . ?
C26A O31A C32A 116.5(5) . . ?
O31B C32B H32D 109.5 . . ?
O31B C32B H32E 109.5 . . ?
H32D C32B H32E 109.5 . . ?
O31B C32B H32F 109.5 . . ?
H32D C32B H32F 109.5 . . ?
H32E C32B H32F 109.5 . . ?
O31A C32A H32A 109.5 . . ?
O31A C32A H32B 109.5 . . ?
H32A C32A H32B 109.5 . . ?
O31A C32A H32C 109.5 . . ?
H32A C32A H32C 109.5 . . ?
H32B C32A H32C 109.5 . . ?
C34B C33B C22B 113.3(5) . . ?
C34B C33B C37B 111.1(5) . . ?
C22B C33B C37B 113.4(6) . . ?
C34B C33B H33B 106.1 . . ?
C22B C33B H33B 106.1 . . ?
C37B C33B H33B 106.1 . . ?
C34A C33A C22A 113.0(6) . . ?
C34A C33A C37A 110.6(6) . . ?
C22A C33A C37A 111.8(5) . . ?
C34A C33A H33A 107.0 . . ?
C22A C33A H33A 107.0 . . ?
C37A C33A H33A 107.0 . . ?
O36B C34B O35B 120.6(7) . . ?
O36B C34B C33B 126.0(6) . . ?
O35B C34B C33B 113.4(6) . . ?
O36A C34A O35A 120.0(8) . . ?
O36A C34A C33A 124.0(8) . . ?
O35A C34A C33A 116.0(8) . . ?
C34B O35B H35B 111(4) . . ?
C34A O35A H35A 107(4) . . ?
C33B C37B H37D 109.5 . . ?
C33B C37B H37E 109.5 . . ?
H37D C37B H37E 109.5 . . ?
C33B C37B H37F 109.5 . . ?
H37D C37B H37F 109.5 . . ?
H37E C37B H37F 109.5 . . ?
C33A C37A H37A 109.5 . . ?
C33A C37A H37B 109.5 . . ?
H37A C37A H37B 109.5 . . ?
C33A C37A H37C 109.5 . . ?
H37A C37A H37C 109.5 . . ?
H37B C37A H37C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11C C1C C2C C3C 0.1(12) . . . . ?
C11A C1A C2A C3A 0.8(13) . . . . ?
C11B C1B C2B C3B -0.6(11) . . . . ?
C1C C2C C3C C4C -2.1(13) . . . . ?
C1A C2A C3A C4A -1.0(13) . . . . ?
C1B C2B C3B C4B 1.3(12) . . . . ?
C2C C3C C4C C12C 2.0(12) . . . . ?
C2A C3A C4A C12A 1.8(13) . . . . ?
C2B C3B C4B C12B -1.1(11) . . . . ?
C14C C5C C6C C7C -0.2(12) . . . . ?
C14A C5A C6A C7A -0.4(11) . . . . ?
C14B C5B C6B C7B 1.0(11) . . . . ?
C5C C6C C7C C8C -0.2(13) . . . . ?
C5A C6A C7A C8A -0.1(11) . . . . ?
C5B C6B C7B C8B -0.9(12) . . . . ?
C6C C7C C8C C13C 0.7(12) . . . . ?
C6A C7A C8A C13A 0.7(11) . . . . ?
C6B C7B C8B C13B 0.0(11) . . . . ?
C13C N10C C11C C1C 179.1(6) . . . . ?
C13C N10C C11C C12C -0.8(9) . . . . ?
C2C C1C C11C N10C -178.0(7) . . . . ?
C2C C1C C11C C12C 1.9(11) . . . . ?
C13A N10A C11A C1A 176.6(6) . . . . ?
C13A N10A C11A C12A -1.3(10) . . . . ?
C2A C1A C11A N10A -179.2(7) . . . . ?
C2A C1A C11A C12A -1.2(11) . . . . ?
C13B N10B C11B C12B 0.6(9) . . . . ?
C13B N10B C11B C1B -178.8(5) . . . . ?
C2B C1B C11B N10B 179.1(6) . . . . ?
C2B C1B C11B C12B -0.4(9) . . . . ?
C14C C9C C12C C11C 2.3(9) . . . . ?
C14C C9C C12C C4C -176.7(6) . . . . ?
N10C C11C C12C C9C -1.1(10) . . . . ?
C1C C11C C12C C9C 179.0(6) . . . . ?
N10C C11C C12C C4C 178.0(6) . . . . ?
C1C C11C C12C C4C -1.9(9) . . . . ?
C3C C4C C12C C9C 179.0(7) . . . . ?
C3C C4C C12C C11C 0.0(10) . . . . ?
C14A C9A C12A C4A -178.6(7) . . . . ?
C14A C9A C12A C11A 0.6(10) . . . . ?
C3A C4A C12A C9A 176.9(8) . . . . ?
C3A C4A C12A C11A -2.2(12) . . . . ?
N10A C11A C12A C9A 0.6(10) . . . . ?
C1A C11A C12A C9A -177.3(7) . . . . ?
N10A C11A C12A C4A 179.8(6) . . . . ?
C1A C11A C12A C4A 1.9(10) . . . . ?
C14B C9B C12B C11B 1.0(9) . . . . ?
C14B C9B C12B C4B 179.0(6) . . . . ?
N10B C11B C12B C9B -0.8(9) . . . . ?
C1B C11B C12B C9B 178.6(5) . . . . ?
N10B C11B C12B C4B -178.8(6) . . . . ?
C1B C11B C12B C4B 0.6(9) . . . . ?
C3B C4B C12B C9B -177.8(6) . . . . ?
C3B C4B C12B C11B 0.1(10) . . . . ?
C11C N10C C13C C14C 1.6(10) . . . . ?
C11C N10C C13C C8C -178.1(6) . . . . ?
C7C C8C C13C N10C 179.0(7) . . . . ?
C7C C8C C13C C14C -0.7(10) . . . . ?
C11A N10A C13A C8A -177.8(6) . . . . ?
C11A N10A C13A C14A 0.8(10) . . . . ?
C7A C8A C13A N10A 177.9(6) . . . . ?
C7A C8A C13A C14A -0.7(10) . . . . ?
C11B N10B C13B C8B -179.5(6) . . . . ?
C11B N10B C13B C14B -0.6(8) . . . . ?
C7B C8B C13B N10B 179.8(6) . . . . ?
C7B C8B C13B C14B 0.9(9) . . . . ?
C12C C9C C14C C13C -1.6(9) . . . . ?
C12C C9C C14C C5C 177.4(6) . . . . ?
N10C C13C C14C C9C -0.4(10) . . . . ?
C8C C13C C14C C9C 179.3(6) . . . . ?
N10C C13C C14C C5C -179.4(6) . . . . ?
C8C C13C C14C C5C 0.2(9) . . . . ?
C6C C5C C14C C9C -178.8(7) . . . . ?
C6C C5C C14C C13C 0.2(10) . . . . ?
C12A C9A C14A C5A 177.7(6) . . . . ?
C12A C9A C14A C13A -1.1(10) . . . . ?
C6A C5A C14A C9A -178.3(7) . . . . ?
C6A C5A C14A C13A 0.4(10) . . . . ?
N10A C13A C14A C9A 0.4(10) . . . . ?
C8A C13A C14A C9A 179.0(6) . . . . ?
N10A C13A C14A C5A -178.4(6) . . . . ?
C8A C13A C14A C5A 0.2(9) . . . . ?
C12B C9B C14B C5B 179.5(6) . . . . ?
C12B C9B C14B C13B -1.0(9) . . . . ?
C6B C5B C14B C9B 179.4(7) . . . . ?
C6B C5B C14B C13B -0.2(9) . . . . ?
N10B C13B C14B C9B 0.8(9) . . . . ?
C8B C13B C14B C9B 179.7(6) . . . . ?
N10B C13B C14B C5B -179.6(6) . . . . ?
C8B C13B C14B C5B -0.8(8) . . . . ?
C29B C21B C22B C23B 0.1(8) . . . . ?
C29B C21B C22B C33B 177.8(5) . . . . ?
C29A C21A C22A C23A 0.0(9) . . . . ?
C29A C21A C22A C33A -177.2(6) . . . . ?
C21B C22B C23B C24B 0.3(8) . . . . ?
C33B C22B C23B C24B -177.5(5) . . . . ?
C21A C22A C23A C24A -0.5(9) . . . . ?
C33A C22A C23A C24A 176.9(6) . . . . ?
C22B C23B C24B C30B -0.9(9) . . . . ?
C22A C23A C24A C30A -0.1(9) . . . . ?
C30B C25B C26B O31B -178.7(6) . . . . ?
C30B C25B C26B C27B 1.3(10) . . . . ?
C30A C25A C26A O31A -178.9(5) . . . . ?
C30A C25A C26A C27A 1.6(9) . . . . ?
C25B C26B C27B C28B -0.9(11) . . . . ?
O31B C26B C27B C28B 179.1(6) . . . . ?
C25A C26A C27A C28A -0.8(9) . . . . ?
O31A C26A C27A C28A 179.7(5) . . . . ?
C26B C27B C28B C29B -1.0(10) . . . . ?
C26A C27A C28A C29A -0.6(9) . . . . ?
C27B C28B C29B C30B 2.3(9) . . . . ?
C27B C28B C29B C21B -177.9(6) . . . . ?
C22B C21B C29B C30B 0.1(9) . . . . ?
C22B C21B C29B C28B -179.8(6) . . . . ?
C27A C28A C29A C30A 1.1(8) . . . . ?
C27A C28A C29A C21A -177.6(5) . . . . ?
C22A C21A C29A C30A 1.1(8) . . . . ?
C22A C21A C29A C28A 179.8(6) . . . . ?
C23B C24B C30B C29B 1.1(9) . . . . ?
C23B C24B C30B C25B -177.9(6) . . . . ?
C28B C29B C30B C24B 179.2(5) . . . . ?
C21B C29B C30B C24B -0.7(8) . . . . ?
C28B C29B C30B C25B -1.8(8) . . . . ?
C21B C29B C30B C25B 178.4(5) . . . . ?
C26B C25B C30B C24B 179.0(6) . . . . ?
C26B C25B C30B C29B 0.0(9) . . . . ?
C28A C29A C30A C24A 179.6(5) . . . . ?
C21A C29A C30A C24A -1.7(8) . . . . ?
C28A C29A C30A C25A -0.2(8) . . . . ?
C21A C29A C30A C25A 178.5(5) . . . . ?
C23A C24A C30A C29A 1.2(8) . . . . ?
C23A C24A C30A C25A -179.0(5) . . . . ?
C26A C25A C30A C29A -1.1(8) . . . . ?
C26A C25A C30A C24A 179.0(6) . . . . ?
C25B C26B O31B C32B 11.0(10) . . . . ?
C27B C26B O31B C32B -169.0(6) . . . . ?
C25A C26A O31A C32A 0.9(8) . . . . ?
C27A C26A O31A C32A -179.6(5) . . . . ?
C21B C22B C33B C34B 109.2(7) . . . . ?
C23B C22B C33B C34B -73.1(7) . . . . ?
C21B C22B C33B C37B -123.0(6) . . . . ?
C23B C22B C33B C37B 54.7(7) . . . . ?
C21A C22A C33A C34A -42.7(9) . . . . ?
C23A C22A C33A C34A 140.1(7) . . . . ?
C21A C22A C33A C37A 82.9(8) . . . . ?
C23A C22A C33A C37A -94.4(7) . . . . ?
C22B C33B C34B O36B 3.4(10) . . . . ?
C37B C33B C34B O36B -125.6(7) . . . . ?
C22B C33B C34B O35B -175.7(6) . . . . ?
C37B C33B C34B O35B 55.3(7) . . . . ?
C22A C33A C34A O36A 92.4(9) . . . . ?
C37A C33A C34A O36A -33.8(10) . . . . ?
C22A C33A C34A O35A -87.5(7) . . . . ?
C37A C33A C34A O35A 146.3(6) . . . . ?

_refine_diff_density_max         0.161
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.031



####################################################################### 
# 
# 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_global_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2168757'
loop_
_audit_author_name
_audit_author_address
'Artur Sikorski'
;University of Gdansk, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2022-04-26 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_journal_coeditor_?tes           
; ?
;
_iucr_compatibility_tag          ACTA95
loop_
_publ_author_foot?te
;
?
;
;
?
;
;
?
;
;
?
;
;
?
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 O3, C14 H13 O3, C13 H11 N2, H2 O'
_chemical_formula_sum            'C41 H40 N2 O7'
_chemical_formula_weight         672.75

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   10.0768(11)
_cell_length_b                   6.2918(5)
_cell_length_c                   27.347(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.004(11)
_cell_angle_gamma                90
_cell_volume                     1717.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    11483
_cell_measurement_theta_min      3.324
_cell_measurement_theta_max      25.00

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.996
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   
;
CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd.,
2008)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      295(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  'Oxford Diffraction Ruby CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.4002
_diffrn_reflns_number            11483
_diffrn_reflns_av_unetI/netI     0.1574
_diffrn_reflns_av_R_equivalents  0.0978
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.324
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_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 0.913
_diffrn_reflns_point_group_measured_fraction_full 0.913
_reflns_number_total             5516
_reflns_number_gt                2362
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.666
_reflns_Friedel_fraction_max     0.810
_reflns_Friedel_fraction_full    0.810

_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       
'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_cell_refinement       
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0041P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 517 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   3.2(10)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         5516
_refine_ls_number_parameters     473
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1928
_refine_ls_R_factor_gt           0.0677
_refine_ls_wR_factor_ref         0.1174
_refine_ls_wR_factor_gt          0.0842
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_restrained_S_all      0.940
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.001

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
O1W O 0.5828(9) 0.2015(12) 0.2197(4) 0.160(4) Uani 1 1 d D . . . .
H1W H 0.636(3) 0.090(4) 0.214(3) 0.241 Uiso 1 1 d D U . . .
H2W H 0.626(11) 0.343(11) 0.216(5) 0.241 Uiso 1 1 d D U . . .
C1 C 0.0712(10) -0.1568(15) 0.2142(3) 0.080(3) Uani 1 1 d . . . . .
H1 H -0.014972 -0.174344 0.222061 0.096 Uiso 1 1 calc R U . . .
C2 C 0.1209(12) -0.3063(14) 0.1847(4) 0.083(3) Uani 1 1 d . . . . .
H2 H 0.069289 -0.423970 0.173808 0.100 Uiso 1 1 calc R U . . .
C3 C 0.2478(12) -0.2818(16) 0.1713(4) 0.089(3) Uani 1 1 d . . . . .
H3 H 0.279722 -0.381168 0.150658 0.106 Uiso 1 1 calc R U . . .
C4 C 0.3258(10) -0.1145(15) 0.1881(4) 0.085(3) Uani 1 1 d . . . . .
H4 H 0.411256 -0.098467 0.179466 0.102 Uiso 1 1 calc DR U . . .
C5 C 0.4007(9) 0.5202(14) 0.2859(3) 0.069(3) Uani 1 1 d . . . . .
H5 H 0.485971 0.527281 0.276717 0.083 Uiso 1 1 calc R U . . .
C6 C 0.3588(10) 0.6713(14) 0.3158(3) 0.069(3) Uani 1 1 d . . . . .
H6 H 0.414878 0.783973 0.326787 0.082 Uiso 1 1 calc R U . . .
C7 C 0.2311(10) 0.6567(14) 0.3298(4) 0.073(3) Uani 1 1 d . . . . .
H7 H 0.203059 0.758459 0.350834 0.087 Uiso 1 1 calc R U . . .
C8 C 0.1481(10) 0.4968(14) 0.3133(4) 0.073(3) Uani 1 1 d . . . . .
H8 H 0.064103 0.490503 0.323589 0.087 Uiso 1 1 calc R U . . .
C9 C 0.1008(12) 0.1737(14) 0.2620(4) 0.077(3) Uani 1 1 d . . . . .
N10 N 0.3539(9) 0.2014(15) 0.2379(3) 0.094(3) Uani 1 1 d D . . . .
H10 H 0.449(4) 0.207(17) 0.236(4) 0.113 Uiso 1 1 d D U . . .
C11 C 0.1454(12) 0.0199(15) 0.2327(4) 0.074(3) Uani 1 1 d . . . . .
C12 C 0.2740(13) 0.0352(13) 0.2191(4) 0.079(3) Uani 1 1 d . . . . .
C13 C 0.1829(11) 0.3403(15) 0.2813(4) 0.068(3) Uani 1 1 d . . . . .
C14 C 0.3133(11) 0.3523(13) 0.2691(3) 0.068(3) Uani 1 1 d . . . . .
N15 N -0.0537(11) 0.1614(16) 0.2730(5) 0.119(4) Uani 1 1 d . . . . .
H15A H -0.124(11) 0.084(19) 0.264(5) 0.143 Uiso 1 1 d . U . . .
H15B H -0.098(12) 0.250(17) 0.290(4) 0.143 Uiso 1 1 d . U . . .
C21B C 0.8716(7) 0.6287(12) 0.0826(3) 0.049(2) Uani 1 1 d . . . . .
H21B H 0.837894 0.761265 0.072231 0.058 Uiso 1 1 calc R U . . .
C21A C 0.5852(7) 0.7462(12) 0.4253(3) 0.053(2) Uani 1 1 d . . . . .
H21A H 0.606573 0.611759 0.438245 0.064 Uiso 1 1 calc R U . . .
C22B C 0.8023(8) 0.5055(13) 0.1118(3) 0.051(2) Uani 1 1 d . . . . .
C22A C 0.6666(7) 0.8371(13) 0.3961(3) 0.052(2) Uani 1 1 d . . . . .
C23B C 0.8531(8) 0.3014(13) 0.1262(3) 0.060(3) Uani 1 1 d . . . . .
H23B H 0.806487 0.214945 0.145550 0.072 Uiso 1 1 calc R U . . .
C23A C 0.6325(8) 1.0407(13) 0.3760(3) 0.057(2) Uani 1 1 d . . . . .
H23A H 0.687735 1.105400 0.355837 0.068 Uiso 1 1 calc R U . . .
C24B C 0.9688(8) 0.2316(11) 0.1121(3) 0.056(2) Uani 1 1 d . . . . .
H24B H 0.999283 0.096434 0.121765 0.067 Uiso 1 1 calc R U . . .
C24A C 0.5198(8) 1.1433(12) 0.3857(3) 0.055(2) Uani 1 1 d . . . . .
H24A H 0.498307 1.276254 0.372004 0.066 Uiso 1 1 calc R U . . .
C25B C 1.1700(8) 0.2876(12) 0.0701(3) 0.053(2) Uani 1 1 d . . . . .
H25B H 1.205045 0.155821 0.080458 0.063 Uiso 1 1 calc R U . . .
C25A C 0.3184(7) 1.1526(11) 0.4282(3) 0.050(2) Uani 1 1 d . . . . .
H25A H 0.294652 1.284226 0.414228 0.060 Uiso 1 1 calc R U . . .
C26B C 1.2375(8) 0.4162(13) 0.0423(3) 0.058(2) Uani 1 1 d . . . . .
C26A C 0.2407(8) 1.0625(12) 0.4594(3) 0.053(2) Uani 1 1 d . . . . .
C27B C 1.1855(8) 0.6143(12) 0.0260(3) 0.059(3) Uani 1 1 d . . . . .
H27B H 1.232660 0.698346 0.006365 0.070 Uiso 1 1 calc R U . . .
C27A C 0.2772(8) 0.8601(13) 0.4800(3) 0.057(2) Uani 1 1 d . . . . .
H27A H 0.225092 0.798368 0.501665 0.068 Uiso 1 1 calc R U . . .
C28B C 1.0674(7) 0.6855(12) 0.0384(3) 0.051(2) Uani 1 1 d . . . . .
H28B H 1.034698 0.817913 0.027355 0.061 Uiso 1 1 calc R U . . .
C28A C 0.3862(8) 0.7550(12) 0.4687(3) 0.056(2) Uani 1 1 d . . . . .
H28A H 0.406672 0.620763 0.481836 0.067 Uiso 1 1 calc R U . . .
C29B C 0.9933(7) 0.5580(11) 0.0681(3) 0.0401(19) Uani 1 1 d . . . . .
C29A C 0.4688(7) 0.8482(12) 0.4371(3) 0.047(2) Uani 1 1 d . . . . .
C30B C 1.0451(8) 0.3555(12) 0.0834(3) 0.047(2) Uani 1 1 d . . . . .
C30A C 0.4361(7) 1.0478(11) 0.4166(3) 0.0412(19) Uani 1 1 d . . . . .
O31B O 1.3580(6) 0.3690(10) 0.0279(2) 0.0774(18) Uani 1 1 d . . . . .
O31A O 0.1296(5) 1.1480(9) 0.4750(2) 0.0690(18) Uani 1 1 d . . . . .
C32B C 1.4212(9) 0.1773(18) 0.0460(4) 0.111(4) Uani 1 1 d . . . . .
H32D H 1.503970 0.160334 0.032865 0.167 Uiso 1 1 calc R U . . .
H32E H 1.363276 0.059256 0.036125 0.167 Uiso 1 1 calc R U . . .
H32F H 1.438867 0.182846 0.081438 0.167 Uiso 1 1 calc R U . . .
C32A C 0.0846(9) 1.3438(13) 0.4536(4) 0.095(3) Uani 1 1 d . . . . .
H32A H 0.008224 1.391619 0.467964 0.142 Uiso 1 1 calc R U . . .
H32B H 0.059996 1.325806 0.418659 0.142 Uiso 1 1 calc R U . . .
H32C H 0.155064 1.447201 0.459630 0.142 Uiso 1 1 calc R U . . .
C33B C 0.6740(9) 0.5800(15) 0.1305(4) 0.072(3) Uani 1 1 d . . . . .
H33B H 0.619509 0.454734 0.135292 0.086 Uiso 1 1 calc R U . . .
C33A C 0.7921(7) 0.7258(14) 0.3864(3) 0.064(2) Uani 1 1 d . . . . .
H33A H 0.804967 0.605650 0.409365 0.076 Uiso 1 1 calc R U . . .
C34B C 0.7109(9) 0.6901(15) 0.1807(4) 0.070(3) Uani 1 1 d . . . . .
C34A C 0.7845(8) 0.6346(15) 0.3355(5) 0.070(3) Uani 1 1 d . . . . .
O35B O 0.7271(7) 0.5701(9) 0.2176(3) 0.087(2) Uani 1 1 d D . . . .
O35A O 0.7529(8) 0.7586(11) 0.2993(3) 0.101(3) Uani 1 1 d . . . . .
H35A H 0.799(11) 0.70(2) 0.277(4) 0.152 Uiso 1 1 d . U . . .
O36B O 0.7244(8) 0.8832(10) 0.1841(3) 0.119(3) Uani 1 1 d . . . . .
O36A O 0.8099(8) 0.4478(11) 0.3300(3) 0.113(3) Uani 1 1 d . . . . .
C37B C 0.5906(8) 0.7299(18) 0.0947(4) 0.108(4) Uani 1 1 d . . . . .
H37D H 0.568500 0.660806 0.063279 0.162 Uiso 1 1 calc R U . . .
H37E H 0.641136 0.856479 0.090606 0.162 Uiso 1 1 calc R U . . .
H37F H 0.509721 0.766646 0.107519 0.162 Uiso 1 1 calc R U . . .
C37A C 0.9180(7) 0.8644(16) 0.3969(3) 0.097(3) Uani 1 1 d . . . . .
H37A H 0.921452 0.928269 0.428923 0.145 Uiso 1 1 calc R U . . .
H37B H 0.915206 0.973689 0.372284 0.145 Uiso 1 1 calc R U . . .
H37C H 0.996147 0.777912 0.396059 0.145 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
O1W H1W 0.91(3) . ?
O1W H2W 1.01(2) . ?
C1 C2 1.377(12) . ?
C1 C11 1.395(12) . ?
C1 H1 0.9300 . ?
C2 C3 1.387(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.355(12) . ?
C3 H3 0.9300 . ?
C4 C12 1.414(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.358(11) . ?
C5 C14 1.411(11) . ?
C5 H5 0.9300 . ?
C6 C7 1.397(11) . ?
C6 H6 0.9300 . ?
C7 C8 1.345(11) . ?
C7 H7 0.9300 . ?
C8 C13 1.393(11) . ?
C8 H8 0.9300 . ?
C9 C11 1.371(12) . ?
C9 C13 1.393(12) . ?
C9 N15 1.629(13) . ?
N10 C14 1.377(12) . ?
N10 C12 1.375(12) . ?
N10 H10 0.97(3) . ?
C11 C12 1.401(12) . ?
C13 C14 1.402(11) . ?
N15 H15A 0.87(11) . ?
N15 H15B 0.88(10) . ?
C21B C22B 1.371(10) . ?
C21B C29B 1.412(9) . ?
C21B H21B 0.9300 . ?
C21A C22A 1.350(9) . ?
C21A C29A 1.413(9) . ?
C21A H21A 0.9300 . ?
C22B C23B 1.418(10) . ?
C22B C33B 1.529(10) . ?
C22A C23A 1.417(11) . ?
C22A C33A 1.502(9) . ?
C23B C24B 1.351(9) . ?
C23B H23B 0.9300 . ?
C23A C24A 1.364(10) . ?
C23A H23A 0.9300 . ?
C24B C30B 1.409(9) . ?
C24B H24B 0.9300 . ?
C24A C30A 1.409(9) . ?
C24A H24A 0.9300 . ?
C25B C26B 1.356(9) . ?
C25B C30B 1.422(9) . ?
C25B H25B 0.9300 . ?
C25A C26A 1.359(9) . ?
C25A C30A 1.431(9) . ?
C25A H25A 0.9300 . ?
C26B O31B 1.361(8) . ?
C26B C27B 1.401(10) . ?
C26A O31A 1.363(8) . ?
C26A C27A 1.419(11) . ?
C27B C28B 1.358(9) . ?
C27B H27B 0.9300 . ?
C27A C28A 1.355(9) . ?
C27A H27A 0.9300 . ?
C28B C29B 1.426(9) . ?
C28B H28B 0.9300 . ?
C28A C29A 1.408(9) . ?
C28A H28A 0.9300 . ?
C29B C30B 1.417(9) . ?
C29A C30A 1.395(9) . ?
O31B C32B 1.421(11) . ?
O31A C32A 1.411(9) . ?
C32B H32D 0.9600 . ?
C32B H32E 0.9600 . ?
C32B H32F 0.9600 . ?
C32A H32A 0.9600 . ?
C32A H32B 0.9600 . ?
C32A H32C 0.9600 . ?
C33B C37B 1.526(11) . ?
C33B C34B 1.537(13) . ?
C33B H33B 0.9800 . ?
C33A C34A 1.497(13) . ?
C33A C37A 1.533(10) . ?
C33A H33A 0.9800 . ?
C34B O36B 1.224(10) . ?
C34B O35B 1.252(11) . ?
C34A O36A 1.216(9) . ?
C34A O35A 1.267(12) . ?
O35A H35A 0.91(10) . ?
C37B H37D 0.9600 . ?
C37B H37E 0.9600 . ?
C37B H37F 0.9600 . ?
C37A H37A 0.9600 . ?
C37A H37B 0.9600 . ?
C37A H37C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1W O1W H2W 113(8) . . ?
H1W O1W H10 131(5) . . ?
H2W O1W H10 116(9) . . ?
C2 C1 C11 122.4(10) . . ?
C2 C1 H1 118.8 . . ?
C11 C1 H1 118.8 . . ?
C1 C2 C3 120.1(10) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 120.6(10) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C12 118.4(10) . . ?
C3 C4 H4 120.8 . . ?
C12 C4 H4 120.8 . . ?
C6 C5 C14 119.3(9) . . ?
C6 C5 H5 120.4 . . ?
C14 C5 H5 120.4 . . ?
C5 C6 C7 119.6(9) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 120.6(9) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C13 122.8(9) . . ?
C7 C8 H8 118.6 . . ?
C13 C8 H8 118.6 . . ?
C11 C9 C13 121.8(11) . . ?
C11 C9 N15 118.3(10) . . ?
C13 C9 N15 119.9(9) . . ?
C14 N10 C12 123.2(9) . . ?
C14 N10 H10 113(7) . . ?
C12 N10 H10 123(7) . . ?
C9 C11 C1 124.9(11) . . ?
C9 C11 C12 119.8(10) . . ?
C1 C11 C12 115.3(10) . . ?
N10 C12 C11 117.9(9) . . ?
N10 C12 C4 119.0(11) . . ?
C11 C12 C4 123.1(10) . . ?
C9 C13 C8 125.6(10) . . ?
C9 C13 C14 118.5(10) . . ?
C8 C13 C14 115.9(9) . . ?
N10 C14 C13 118.7(9) . . ?
N10 C14 C5 119.5(10) . . ?
C13 C14 C5 121.7(9) . . ?
C9 N15 H15A 138(8) . . ?
C9 N15 H15B 129(8) . . ?
H15A N15 H15B 93(10) . . ?
C22B C21B C29B 121.2(7) . . ?
C22B C21B H21B 119.4 . . ?
C29B C21B H21B 119.4 . . ?
C22A C21A C29A 122.3(7) . . ?
C22A C21A H21A 118.9 . . ?
C29A C21A H21A 118.9 . . ?
C21B C22B C23B 118.7(7) . . ?
C21B C22B C33B 123.0(8) . . ?
C23B C22B C33B 118.3(7) . . ?
C21A C22A C23A 118.6(7) . . ?
C21A C22A C33A 120.2(8) . . ?
C23A C22A C33A 121.2(8) . . ?
C24B C23B C22B 120.5(7) . . ?
C24B C23B H23B 119.8 . . ?
C22B C23B H23B 119.8 . . ?
C24A C23A C22A 121.0(8) . . ?
C24A C23A H23A 119.5 . . ?
C22A C23A H23A 119.5 . . ?
C23B C24B C30B 122.6(8) . . ?
C23B C24B H24B 118.7 . . ?
C30B C24B H24B 118.7 . . ?
C23A C24A C30A 120.0(8) . . ?
C23A C24A H24A 120.0 . . ?
C30A C24A H24A 120.0 . . ?
C26B C25B C30B 119.6(7) . . ?
C26B C25B H25B 120.2 . . ?
C30B C25B H25B 120.2 . . ?
C26A C25A C30A 121.0(7) . . ?
C26A C25A H25A 119.5 . . ?
C30A C25A H25A 119.5 . . ?
C25B C26B O31B 124.8(8) . . ?
C25B C26B C27B 121.0(7) . . ?
O31B C26B C27B 114.2(7) . . ?
C25A C26A O31A 127.0(8) . . ?
C25A C26A C27A 118.8(7) . . ?
O31A C26A C27A 114.2(7) . . ?
C28B C27B C26B 121.1(7) . . ?
C28B C27B H27B 119.5 . . ?
C26B C27B H27B 119.5 . . ?
C28A C27A C26A 121.4(7) . . ?
C28A C27A H27A 119.3 . . ?
C26A C27A H27A 119.3 . . ?
C27B C28B C29B 120.2(7) . . ?
C27B C28B H28B 119.9 . . ?
C29B C28B H28B 119.9 . . ?
C27A C28A C29A 120.3(7) . . ?
C27A C28A H28A 119.9 . . ?
C29A C28A H28A 119.9 . . ?
C21B C29B C30B 120.0(6) . . ?
C21B C29B C28B 121.8(7) . . ?
C30B C29B C28B 118.2(6) . . ?
C30A C29A C28A 119.6(7) . . ?
C30A C29A C21A 118.4(7) . . ?
C28A C29A C21A 122.0(8) . . ?
C24B C30B C29B 117.0(7) . . ?
C24B C30B C25B 123.1(7) . . ?
C29B C30B C25B 119.8(7) . . ?
C29A C30A C24A 119.8(7) . . ?
C29A C30A C25A 118.8(7) . . ?
C24A C30A C25A 121.4(7) . . ?
C26B O31B C32B 117.2(7) . . ?
C26A O31A C32A 116.4(7) . . ?
O31B C32B H32D 109.5 . . ?
O31B C32B H32E 109.5 . . ?
H32D C32B H32E 109.5 . . ?
O31B C32B H32F 109.5 . . ?
H32D C32B H32F 109.5 . . ?
H32E C32B H32F 109.5 . . ?
O31A C32A H32A 109.5 . . ?
O31A C32A H32B 109.5 . . ?
H32A C32A H32B 109.5 . . ?
O31A C32A H32C 109.5 . . ?
H32A C32A H32C 109.5 . . ?
H32B C32A H32C 109.5 . . ?
C37B C33B C22B 113.0(7) . . ?
C37B C33B C34B 109.8(8) . . ?
C22B C33B C34B 109.1(7) . . ?
C37B C33B H33B 108.3 . . ?
C22B C33B H33B 108.3 . . ?
C34B C33B H33B 108.3 . . ?
C34A C33A C22A 114.1(7) . . ?
C34A C33A C37A 109.0(7) . . ?
C22A C33A C37A 113.4(7) . . ?
C34A C33A H33A 106.6 . . ?
C22A C33A H33A 106.6 . . ?
C37A C33A H33A 106.6 . . ?
O36B C34B O35B 122.5(11) . . ?
O36B C34B C33B 121.6(10) . . ?
O35B C34B C33B 115.9(8) . . ?
O36A C34A O35A 122.2(11) . . ?
O36A C34A C33A 120.0(11) . . ?
O35A C34A C33A 117.8(9) . . ?
C34A O35A H35A 101(8) . . ?
C33B C37B H37D 109.5 . . ?
C33B C37B H37E 109.5 . . ?
H37D C37B H37E 109.5 . . ?
C33B C37B H37F 109.5 . . ?
H37D C37B H37F 109.5 . . ?
H37E C37B H37F 109.5 . . ?
C33A C37A H37A 109.5 . . ?
C33A C37A H37B 109.5 . . ?
H37A C37A H37B 109.5 . . ?
C33A C37A H37C 109.5 . . ?
H37A C37A H37C 109.5 . . ?
H37B C37A H37C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C1 C2 C3 -1.6(15) . . . . ?
C1 C2 C3 C4 1.9(15) . . . . ?
C2 C3 C4 C12 -0.7(15) . . . . ?
C14 C5 C6 C7 0.9(13) . . . . ?
C5 C6 C7 C8 -1.4(14) . . . . ?
C6 C7 C8 C13 -0.7(15) . . . . ?
C13 C9 C11 C1 176.6(8) . . . . ?
N15 C9 C11 C1 -4.8(14) . . . . ?
C13 C9 C11 C12 -3.9(14) . . . . ?
N15 C9 C11 C12 174.7(8) . . . . ?
C2 C1 C11 C9 179.8(10) . . . . ?
C2 C1 C11 C12 0.2(13) . . . . ?
C14 N10 C12 C11 -0.1(14) . . . . ?
C14 N10 C12 C4 -178.7(9) . . . . ?
C9 C11 C12 N10 3.0(13) . . . . ?
C1 C11 C12 N10 -177.4(8) . . . . ?
C9 C11 C12 C4 -178.5(9) . . . . ?
C1 C11 C12 C4 1.1(14) . . . . ?
C3 C4 C12 N10 177.6(9) . . . . ?
C3 C4 C12 C11 -0.8(15) . . . . ?
C11 C9 C13 C8 -176.6(9) . . . . ?
N15 C9 C13 C8 4.8(14) . . . . ?
C11 C9 C13 C14 1.8(13) . . . . ?
N15 C9 C13 C14 -176.8(8) . . . . ?
C7 C8 C13 C9 -178.5(9) . . . . ?
C7 C8 C13 C14 3.1(14) . . . . ?
C12 N10 C14 C13 -1.9(14) . . . . ?
C12 N10 C14 C5 -178.8(8) . . . . ?
C9 C13 C14 N10 1.1(12) . . . . ?
C8 C13 C14 N10 179.6(8) . . . . ?
C9 C13 C14 C5 177.9(8) . . . . ?
C8 C13 C14 C5 -3.6(13) . . . . ?
C6 C5 C14 N10 178.4(9) . . . . ?
C6 C5 C14 C13 1.7(13) . . . . ?
C29B C21B C22B C23B -1.7(12) . . . . ?
C29B C21B C22B C33B 176.8(8) . . . . ?
C29A C21A C22A C23A -0.9(12) . . . . ?
C29A C21A C22A C33A 177.6(8) . . . . ?
C21B C22B C23B C24B 1.1(13) . . . . ?
C33B C22B C23B C24B -177.6(8) . . . . ?
C21A C22A C23A C24A -0.2(13) . . . . ?
C33A C22A C23A C24A -178.6(8) . . . . ?
C22B C23B C24B C30B 0.8(13) . . . . ?
C22A C23A C24A C30A 0.7(12) . . . . ?
C30B C25B C26B O31B 179.3(7) . . . . ?
C30B C25B C26B C27B -0.7(13) . . . . ?
C30A C25A C26A O31A 177.3(7) . . . . ?
C30A C25A C26A C27A -0.9(12) . . . . ?
C25B C26B C27B C28B 1.4(13) . . . . ?
O31B C26B C27B C28B -178.6(7) . . . . ?
C25A C26A C27A C28A -0.8(12) . . . . ?
O31A C26A C27A C28A -179.2(7) . . . . ?
C26B C27B C28B C29B -0.4(12) . . . . ?
C26A C27A C28A C29A 1.9(13) . . . . ?
C22B C21B C29B C30B 0.6(11) . . . . ?
C22B C21B C29B C28B -179.2(8) . . . . ?
C27B C28B C29B C21B 178.6(7) . . . . ?
C27B C28B C29B C30B -1.2(11) . . . . ?
C27A C28A C29A C30A -1.2(12) . . . . ?
C27A C28A C29A C21A 178.4(8) . . . . ?
C22A C21A C29A C30A 1.4(12) . . . . ?
C22A C21A C29A C28A -178.3(8) . . . . ?
C23B C24B C30B C29B -1.9(12) . . . . ?
C23B C24B C30B C25B 177.1(8) . . . . ?
C21B C29B C30B C24B 1.2(10) . . . . ?
C28B C29B C30B C24B -179.0(8) . . . . ?
C21B C29B C30B C25B -177.9(7) . . . . ?
C28B C29B C30B C25B 1.9(10) . . . . ?
C26B C25B C30B C24B -180.0(8) . . . . ?
C26B C25B C30B C29B -1.0(12) . . . . ?
C28A C29A C30A C24A 178.8(8) . . . . ?
C21A C29A C30A C24A -0.8(11) . . . . ?
C28A C29A C30A C25A -0.4(10) . . . . ?
C21A C29A C30A C25A 180.0(7) . . . . ?
C23A C24A C30A C29A -0.2(11) . . . . ?
C23A C24A C30A C25A 179.0(8) . . . . ?
C26A C25A C30A C29A 1.5(11) . . . . ?
C26A C25A C30A C24A -177.7(8) . . . . ?
C25B C26B O31B C32B -4.4(12) . . . . ?
C27B C26B O31B C32B 175.6(8) . . . . ?
C25A C26A O31A C32A 5.2(12) . . . . ?
C27A C26A O31A C32A -176.6(8) . . . . ?
C21B C22B C33B C37B 31.9(12) . . . . ?
C23B C22B C33B C37B -149.5(8) . . . . ?
C21B C22B C33B C34B -90.5(10) . . . . ?
C23B C22B C33B C34B 88.0(10) . . . . ?
C21A C22A C33A C34A 106.7(10) . . . . ?
C23A C22A C33A C34A -74.9(10) . . . . ?
C21A C22A C33A C37A -127.7(9) . . . . ?
C23A C22A C33A C37A 50.7(11) . . . . ?
C37B C33B C34B O36B -29.5(12) . . . . ?
C22B C33B C34B O36B 94.8(11) . . . . ?
C37B C33B C34B O35B 151.1(8) . . . . ?
C22B C33B C34B O35B -84.6(10) . . . . ?
C22A C33A C34A O36A -126.0(9) . . . . ?
C37A C33A C34A O36A 106.1(10) . . . . ?
C22A C33A C34A O35A 54.8(11) . . . . ?
C37A C33A C34A O35A -73.1(11) . . . . ?

_refine_diff_density_max         0.123
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.034



####################################################################### 
# 
# 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_00000001
_database_code_depnum_ccdc_archive 'CCDC 2169121'
loop_
_audit_author_name
_audit_author_address
'Mattia Lopresti'
;University of Eastern Piedmont
Italy
;
_audit_update_record             
;
2022-04-27 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_ATOM007_00000001            
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: All atom refined isotropically because solved from powder diffraction data
;
_vrf_GEOM001_00000001            
;
PROBLEM: _geom_bond_atom_site_label_1 is missing
RESPONSE: Not given
;
_vrf_GEOM002_00000001            
;
PROBLEM: _geom_bond_atom_site_label_2 is missing
RESPONSE: Not given
;
_vrf_GEOM003_00000001            
;
PROBLEM: _geom_bond_distance is missing
RESPONSE: Not given
;
_vrf_GEOM006_00000001            
;
PROBLEM: _geom_angle_atom_site_label_2 is missing
RESPONSE: Not given
;
_vrf_GEOM007_00000001            
;
PROBLEM: _geom_angle_atom_site_label_3 is missing
RESPONSE: Not given
;
_vrf_GEOM008_00000001            
;
PROBLEM: _geom_angle is missing
RESPONSE: Not given
;
_vrf_PLAT029_00000001            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.000 Why?
RESPONSE: Not applicable to powder diffraction data
;
_vrf_PLAT043_00000001            
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..     409.46 Check
RESPONSE: We checked the given molecular weight and it is correct
;
_vrf_PLAT201_00000001            
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         17 Report
RESPONSE: All atom refined isotropically because solved from powder diffraction data
;
_vrf_PLAT880_00000001            
;
PROBLEM: No datum for _diffrn_reflns_number supplied ....     Please Do !
RESPONSE: Not applicable to powder diffraction data
;
_vrf_PLAT881_00000001            
;
PROBLEM: No Datum for _diffrn_reflns_av_R_equivalents ...     Please Do !
RESPONSE: Not applicable to powder diffraction data
;
_vrf_PLAT412_00000001            
;
PROBLEM: Short Intra XH3 .. XHn     H20B     ..H28E     .       1.85 Ang.
RESPONSE: Position and rotation of critical hydrgens was checked. The best possibile solution was given according to both crystal packing and agreement value
;
# Added during the CSD deposition process: Wednesday 27 April 2022 02:44 PM
# end Validation Reply Form

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_chemical_absolute_configuration rmad
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 -x,1/2+y,1/2-z
4 1/2+x,1/2-y,-z
_cell_length_a                   12.6466(4)
_cell_length_b                   29.6246(12)
_cell_length_c                   5.63596(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2111.52
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_thermal_displace_type
C1C C 0.9504 0.1661 1.0029 0.0127 Uiso
H1CA H 0.9031 0.143 0.9668 0.0127 Uiso
C2C C 1.02 0.1613 1.1852 0.0127 Uiso
H2CA H 1.0186 0.1346 1.2722 0.0127 Uiso
C3C C 1.0939 0.1948 1.2489 0.0127 Uiso
H3CA H 1.1407 0.1901 1.3744 0.0127 Uiso
C4C C 1.0961 0.234 1.1259 0.0127 Uiso
H4CA H 1.1443 0.2564 1.1674 0.0127 Uiso
C5C C 0.9535 0.3249 0.4649 0.0127 Uiso
H5CA H 0.9989 0.3488 0.4985 0.0127 Uiso
C6C C 0.8863 0.3282 0.2841 0.0127 Uiso
H6CA H 0.8859 0.3541 0.1902 0.0127 Uiso
C7C C 0.8147 0.2924 0.2335 0.0127 Uiso
H7CA H 0.768 0.2953 0.1068 0.0127 Uiso
C8C C 0.8134 0.2539 0.3665 0.0127 Uiso
H8CA H 0.7652 0.2312 0.3318 0.0127 Uiso
C9C C 0.8828 0.2112 0.6868 0.0127 Uiso
H9CA H 0.8347 0.1883 0.6517 0.0127 Uiso
N10C N 1.0258 0.2813 0.7951 0.0127 Uiso
C11C C 0.9503 0.2073 0.8662 0.0127 Uiso
C12C C 1.0252 0.2412 0.9339 0.0127 Uiso
C13C C 0.886 0.2485 0.5586 0.0127 Uiso
C14C C 0.9567 0.2856 0.6071 0.0127 Uiso
C15B C 0.8194567 0.4175951 -0.2183038 0.0127 Uiso
H15D H 0.8676136 0.3930609 -0.1880544 0.0127 Uiso
H15E H 0.8589346 0.4445241 -0.2523115 0.0127 Uiso
H15F H 0.7759046 0.4224391 -0.08065862 0.0127 Uiso
O16B O 0.7543 0.4066 -0.4159 0.0127 Uiso
C17B C 0.6185 0.4274 -0.68 0.0127 Uiso
H17B H 0.6385 0.4031 -0.7748 0.0127 Uiso
C18B C 0.5368 0.4542 -0.7472 0.0127 Uiso
H18B H 0.502 0.448 -0.8895 0.0127 Uiso
C19B C 0.5027 0.491 -0.608 0.0127 Uiso
C20B C 0.4148 0.5182 -0.671 0.0127 Uiso
H20B H 0.3776 0.5122 -0.8101 0.0127 Uiso
C21B C 0.3838 0.5538 -0.5281 0.0127 Uiso
C22B C 0.441 0.5623 -0.3222 0.0127 Uiso
H22B H 0.421 0.5865 -0.2265 0.0127 Uiso
C23B C 0.5245 0.5365 -0.2567 0.0127 Uiso
H23B H 0.5605 0.5432 -0.1168 0.0127 Uiso
C24B C 0.5574 0.4997 -0.3956 0.0127 Uiso
C25B C 0.6441 0.4718 -0.3298 0.0127 Uiso
H25B H 0.6812 0.4779 -0.1907 0.0127 Uiso
C26B C 0.6735 0.4363 -0.4656 0.0127 Uiso
C27B C 0.2884 0.5829 -0.5823 0.0127 Uiso
H27B H 0.2555 0.5909 -0.4303 0.0127 Uiso
C28B C 0.2061 0.557 -0.7268 0.0127 Uiso
H28D H 0.1788739 0.5760515 -0.8506615 0.0127 Uiso
H28E H 0.238387 0.5306688 -0.7961803 0.0127 Uiso
H28F H 0.1491261 0.5478754 -0.6247997 0.0127 Uiso
C29B C 0.3153 0.6259 -0.7031 0.0127 Uiso
O30B O 0.2920154 0.6352794 -0.9072454 0.0127 Uiso
O31B O 0.3673858 0.6541583 -0.569384 0.0127 Uiso
H31B H 0.3658526 0.6793955 -0.6297402 0.0127 Uiso
_chemical_name_systematic        
'2,3-Benzoquinoline/(+)-(S)-2-(6-Methoxynaphthalen-2-yl)propanoic acid'
_chemical_name_common            Acridine/Naproxen
_chemical_formula_moiety         'C13 H9 N, C14 H14 O3'
_chemical_formula_sum            'C27 H23 O3 N'
_chemical_formula_weight         409.46

_exptl_crystal_recrystallization_method 
'Liquid assisted grinding aided by some drops of a solution 50% Ethanol, 50% Water'
_exptl_crystal_description       'Powder sample'
_diffrn_ambient_temperature      295
_diffrn_ambient_pressure         101.325
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.534753
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Advance'
_cell_measurement_reflns_used    31
_cell_measurement_theta_min      5.98
_cell_measurement_theta_max      36
_cell_measurement_temperature    295

#END
_exptl_crystal_colour            Orange
