# Electronic Supplementary Material (ESI) for Molecular Systems Design & Engineering.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_PIRnC6_RT
_database_code_depnum_ccdc_archive 'CCDC 1998574'
loop_
_audit_author_name
_audit_author_address
'Agnieszka Czapik'
;Adam Mickiewicz University in Poznan
Poland
;
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2020-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H28 N2 O4'
_chemical_formula_sum            'C22 H28 N2 O4'
_chemical_formula_weight         384.46

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   5.6790(2)
_cell_length_b                   10.1659(6)
_cell_length_c                   18.9266(11)
_cell_angle_alpha                94.391(5)
_cell_angle_beta                 96.784(4)
_cell_angle_gamma                90.231(4)
_cell_volume                     1081.74(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1134
_cell_measurement_theta_min      4.3450
_cell_measurement_theta_max      71.1080

_exptl_crystal_description       plank
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_F_000             412
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.658
_shelx_estimated_absorpt_T_min   0.779
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.43155
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_reflns_number            7473
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.362
_diffrn_reflns_theta_max         70.061
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4044
_reflns_number_gt                2998
_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 1.171.40.57a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1506P)²+0.0316P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4044
_refine_ls_number_parameters     344
_refine_ls_number_restraints     143
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0697
_refine_ls_wR_factor_ref         0.2442
_refine_ls_wR_factor_gt          0.2223
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.180
_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
O1 O -0.0128(2) 0.11731(14) 0.59095(9) 0.1028(5) Uani 1 1 d . . . . .
O2 O 0.4457(3) 0.48219(14) 0.66819(9) 0.1063(5) Uani 1 1 d . . . . .
O3 O 1.0008(3) 0.38758(15) 0.41829(9) 0.1073(5) Uani 1 1 d . . . . .
O4 O 0.5391(3) 0.02539(14) 0.33931(9) 0.1088(5) Uani 1 1 d . . . . .
N1 N 0.1831(3) 0.30479(14) 0.64455(9) 0.0877(5) Uani 1 1 d . . . . .
N2 N 0.8047(3) 0.20049(14) 0.36465(9) 0.0917(5) Uani 1 1 d . . . . .
C1 C 0.1418(3) 0.19990(16) 0.59269(10) 0.0830(5) Uani 1 1 d . . . . .
C2 C 0.3176(3) 0.21391(14) 0.54161(9) 0.0770(5) Uani 1 1 d . . . . .
C3 C 0.4575(3) 0.32546(14) 0.56513(10) 0.0775(5) Uani 1 1 d . . . . .
C4 C 0.3709(3) 0.38458(16) 0.63154(11) 0.0850(5) Uani 1 1 d . . . . .
C5 C 0.6378(3) 0.36749(15) 0.52891(10) 0.0813(5) Uani 1 1 d . . . . .
H5 H 0.730855 0.441824 0.544759 0.098 Uiso 1 1 calc R U . . .
C6 C 0.6695(3) 0.29067(14) 0.46724(10) 0.0786(5) Uani 1 1 d . . . . .
C7 C 0.5290(3) 0.17948(14) 0.44358(10) 0.0781(5) Uani 1 1 d . . . . .
C8 C 0.3493(3) 0.13720(15) 0.47987(10) 0.0799(5) Uani 1 1 d . . . . .
H8 H 0.256428 0.062771 0.464047 0.096 Uiso 1 1 calc R U . . .
C9 C 0.8452(3) 0.30460(16) 0.41642(11) 0.0861(5) Uani 1 1 d . . . . .
C10 C 0.6151(3) 0.12160(17) 0.37666(11) 0.0865(5) Uani 1 1 d . . . . .
C11 C 0.0414(4) 0.3322(2) 0.70264(13) 0.1076(6) Uani 1 1 d D U . . .
H11A H -0.089946 0.269511 0.696758 0.129 Uiso 0.488(6) 1 d R U P A 1
H11B H -0.024966 0.419471 0.698728 0.129 Uiso 0.488(6) 1 d R U P A 1
H11C H -0.124796 0.320301 0.684368 0.129 Uiso 0.512(6) 1 d R U P A 2
H11D H 0.065824 0.423771 0.720618 0.129 Uiso 0.512(6) 1 d R U P A 2
C17 C 0.9498(4) 0.1751(3) 0.30685(14) 0.1125(7) Uani 1 1 d D U . . .
H17A H 0.978621 0.081289 0.300080 0.135 Uiso 0.488(6) 1 d R U P A 1
H17B H 1.101681 0.220329 0.318870 0.135 Uiso 0.488(6) 1 d R U P A 1
H17C H 0.925321 0.083859 0.288330 0.135 Uiso 0.512(6) 1 d R U P A 2
H17D H 1.115111 0.185549 0.326470 0.135 Uiso 0.512(6) 1 d R U P A 2
C12 C 0.1717(11) 0.3264(6) 0.7779(2) 0.1096(15) Uani 0.488(6) 1 d D U P A 1
H12A H 0.310691 0.383734 0.783679 0.131 Uiso 0.488(6) 1 d R U P A 1
H12B H 0.068521 0.357304 0.812839 0.131 Uiso 0.488(6) 1 d R U P A 1
C13 C 0.246(2) 0.1876(8) 0.7904(5) 0.155(3) Uani 0.488(6) 1 d D U P A 1
H13A H 0.102613 0.133392 0.782046 0.186 Uiso 0.488(6) 1 d R U P A 1
H13B H 0.342443 0.159562 0.753176 0.186 Uiso 0.488(6) 1 d R U P A 1
C14 C 0.3769(19) 0.1513(12) 0.8594(6) 0.174(4) Uani 0.488(6) 1 d D U P A 1
H14A H 0.332035 0.060269 0.863426 0.208 Uiso 0.488(6) 1 d R U P A 1
H14B H 0.304935 0.202879 0.896256 0.208 Uiso 0.488(6) 1 d R U P A 1
C15 C 0.645(2) 0.1593(15) 0.8835(8) 0.224(5) Uani 0.488(6) 1 d D U P A 1
H15A H 0.693459 0.250573 0.895557 0.269 Uiso 0.488(6) 1 d R U P A 1
H15B H 0.730599 0.124073 0.845077 0.269 Uiso 0.488(6) 1 d R U P A 1
C16 C 0.701(4) 0.0789(19) 0.9492(9) 0.216(6) Uani 0.488(6) 1 d D U P A 1
H16A H 0.867606 0.085314 0.964791 0.325 Uiso 0.488(6) 1 d R U P A 1
H16B H 0.656516 -0.011886 0.936512 0.325 Uiso 0.488(6) 1 d R U P A 1
H16C H 0.614166 0.113094 0.987062 0.325 Uiso 0.488(6) 1 d R U P A 1
C18 C 0.8257(17) 0.2228(11) 0.2392(4) 0.132(3) Uani 0.488(6) 1 d D U P A 1
H18A H 0.782034 0.314077 0.248444 0.159 Uiso 0.488(6) 1 d R U P A 1
H18B H 0.680384 0.171747 0.225934 0.159 Uiso 0.488(6) 1 d R U P A 1
C19 C 0.9706(16) 0.2135(8) 0.1760(4) 0.156(3) Uani 0.488(6) 1 d D U P A 1
H19A H 0.860174 0.203185 0.132729 0.187 Uiso 0.488(6) 1 d R U P A 1
H19B H 1.062074 0.133225 0.178389 0.187 Uiso 0.488(6) 1 d R U P A 1
C20 C 1.1443(16) 0.3286(10) 0.1680(5) 0.175(3) Uani 0.488(6) 1 d D U P A 1
H20A H 1.283436 0.326581 0.202987 0.209 Uiso 0.488(6) 1 d R U P A 1
H20B H 1.067616 0.412951 0.174677 0.209 Uiso 0.488(6) 1 d R U P A 1
C21 C 1.216(2) 0.3066(10) 0.0898(6) 0.184(4) Uani 0.488(6) 1 d D U P A 1
H21A H 1.308951 0.227766 0.083610 0.221 Uiso 0.488(6) 1 d R U P A 1
H21B H 1.078161 0.302916 0.054020 0.221 Uiso 0.488(6) 1 d R U P A 1
C22 C 1.359(2) 0.4291(12) 0.0889(10) 0.252(7) Uani 0.488(6) 1 d D U P A 1
H22A H 1.507378 0.420557 0.118381 0.379 Uiso 0.488(6) 1 d R U P A 1
H22B H 1.275738 0.503557 0.107221 0.379 Uiso 0.488(6) 1 d R U P A 1
H22C H 1.389378 0.441667 0.040961 0.379 Uiso 0.488(6) 1 d R U P A 1
C12A C 0.0982(12) 0.2463(10) 0.7632(4) 0.141(2) Uani 0.512(6) 1 d D U P A 2
H12C H 0.007293 0.276591 0.801438 0.169 Uiso 0.512(6) 1 d R U P A 2
H12D H 0.044733 0.157101 0.747038 0.169 Uiso 0.512(6) 1 d R U P A 2
C13A C 0.3514(13) 0.2415(11) 0.7930(5) 0.153(3) Uani 0.512(6) 1 d D U P A 2
H13C H 0.423490 0.179612 0.760661 0.184 Uiso 0.512(6) 1 d R U P A 2
H13D H 0.416970 0.327542 0.786851 0.184 Uiso 0.512(6) 1 d R U P A 2
C14A C 0.450(2) 0.2102(8) 0.8649(5) 0.168(3) Uani 0.512(6) 1 d D U P A 2
H14C H 0.322556 0.218004 0.894597 0.201 Uiso 0.512(6) 1 d R U P A 2
H14D H 0.565306 0.279214 0.882887 0.201 Uiso 0.512(6) 1 d R U P A 2
C15A C 0.569(2) 0.0797(9) 0.8780(5) 0.184(4) Uani 0.512(6) 1 d D U P A 2
H15C H 0.644650 0.045049 0.837117 0.221 Uiso 0.512(6) 1 d R U P A 2
H15D H 0.458720 0.014529 0.890057 0.221 Uiso 0.512(6) 1 d R U P A 2
C16A C 0.754(4) 0.123(2) 0.9421(11) 0.272(10) Uani 0.512(6) 1 d D U P A 2
H16D H 0.680047 0.183298 0.974253 0.409 Uiso 0.512(6) 1 d R U P A 2
H16E H 0.885237 0.166818 0.925803 0.409 Uiso 0.512(6) 1 d R U P A 2
H16F H 0.808937 0.047818 0.966363 0.409 Uiso 0.512(6) 1 d R U P A 2
C18A C 0.9061(18) 0.2585(11) 0.2474(5) 0.156(4) Uani 0.512(6) 1 d D U P A 2
H18C H 0.897363 0.349818 0.265779 0.187 Uiso 0.512(6) 1 d R U P A 2
H18D H 0.754963 0.233878 0.220040 0.187 Uiso 0.512(6) 1 d R U P A 2
C19A C 1.0999(14) 0.2449(10) 0.1993(4) 0.161(3) Uani 0.512(6) 1 d D U P A 2
H19C H 1.121632 0.152825 0.184272 0.193 Uiso 0.512(6) 1 d R U P A 2
H19D H 1.248552 0.280305 0.224132 0.193 Uiso 0.512(6) 1 d R U P A 2
C20A C 1.019(2) 0.3247(13) 0.1330(6) 0.222(4) Uani 0.512(6) 1 d D U P A 2
H20C H 0.922591 0.271531 0.095620 0.266 Uiso 0.512(6) 1 d R U P A 2
H20D H 0.934931 0.404121 0.145990 0.266 Uiso 0.512(6) 1 d R U P A 2
C21A C 1.270(2) 0.356(2) 0.1116(9) 0.260(7) Uani 0.512(6) 1 d D U P A 2
H21C H 1.359081 0.419662 0.145515 0.312 Uiso 0.512(6) 1 d R U P A 2
H21D H 1.362721 0.277722 0.104035 0.312 Uiso 0.512(6) 1 d R U P A 2
C22A C 1.179(3) 0.415(2) 0.0427(8) 0.300(8) Uani 0.512(6) 1 d D U P A 2
H22D H 1.310533 0.447106 0.021364 0.451 Uiso 0.512(6) 1 d R U P A 2
H22E H 1.075573 0.486516 0.053074 0.451 Uiso 0.512(6) 1 d R U P A 2
H22F H 1.092683 0.349446 0.010174 0.451 Uiso 0.512(6) 1 d R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.208(2) . ?
O2 C4 1.212(2) . ?
O3 C9 1.215(2) . ?
O4 C10 1.209(2) . ?
N1 C1 1.392(2) . ?
N1 C4 1.393(2) . ?
N1 C11 1.448(3) . ?
N2 C9 1.385(3) . ?
N2 C10 1.390(2) . ?
N2 C17 1.454(3) . ?
C1 C2 1.483(3) . ?
C2 C8 1.385(3) . ?
C2 C3 1.3955(19) . ?
C3 C5 1.381(3) . ?
C3 C4 1.489(3) . ?
C5 C6 1.384(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.395(2) . ?
C6 C9 1.479(3) . ?
C7 C8 1.380(3) . ?
C7 C10 1.491(3) . ?
C8 H8 0.9300 . ?
C11 C12A 1.500(8) . ?
C11 C12 1.531(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C11 H11D 0.9700 . ?
C17 C18A 1.458(8) . ?
C17 C18 1.502(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C17 H17D 0.9700 . ?
C12 C13 1.502(8) . ?
C12 H12A 0.9701 . ?
C12 H12B 0.9699 . ?
C13 C14 1.498(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9701 . ?
C14 C15 1.534(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9699 . ?
C15 C16 1.543(9) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9701 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9601 . ?
C16 H16C 0.9600 . ?
C18 C19 1.526(8) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.555(8) . ?
C19 H19A 0.9699 . ?
C19 H19B 0.9701 . ?
C20 C21 1.580(8) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.488(9) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9602 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9604 . ?
C12A C13A 1.483(8) . ?
C12A H12C 0.9699 . ?
C12A H12D 0.9700 . ?
C13A C14A 1.467(8) . ?
C13A H13C 0.9700 . ?
C13A H13D 0.9700 . ?
C14A C15A 1.516(8) . ?
C14A H14C 0.9700 . ?
C14A H14D 0.9700 . ?
C15A C16A 1.542(10) . ?
C15A H15C 0.9701 . ?
C15A H15D 0.9700 . ?
C16A H16D 0.9600 . ?
C16A H16E 0.9599 . ?
C16A H16F 0.9600 . ?
C18A C19A 1.509(8) . ?
C18A H18C 0.9700 . ?
C18A H18D 0.9699 . ?
C19A C20A 1.571(8) . ?
C19A H19C 0.9698 . ?
C19A H19D 0.9701 . ?
C20A C21A 1.564(9) . ?
C20A H20C 0.9700 . ?
C20A H20D 0.9700 . ?
C21A C22A 1.512(9) . ?
C21A H21C 0.9698 . ?
C21A H21D 0.9700 . ?
C22A H22D 0.9599 . ?
C22A H22E 0.9600 . ?
C22A H22F 0.9597 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 111.50(17) . . ?
C1 N1 C11 124.51(16) . . ?
C4 N1 C11 123.92(17) . . ?
C9 N2 C10 111.58(17) . . ?
C9 N2 C17 123.64(16) . . ?
C10 N2 C17 124.74(18) . . ?
O1 C1 N1 124.83(19) . . ?
O1 C1 C2 128.63(18) . . ?
N1 C1 C2 106.53(13) . . ?
C8 C2 C3 122.28(17) . . ?
C8 C2 C1 129.80(14) . . ?
C3 C2 C1 107.92(16) . . ?
C5 C3 C2 122.73(17) . . ?
C5 C3 C4 129.64(14) . . ?
C2 C3 C4 107.61(16) . . ?
O2 C4 N1 125.6(2) . . ?
O2 C4 C3 127.98(18) . . ?
N1 C4 C3 106.44(15) . . ?
C3 C5 C6 114.97(15) . . ?
C3 C5 H5 122.5 . . ?
C6 C5 H5 122.5 . . ?
C5 C6 C7 122.29(17) . . ?
C5 C6 C9 129.72(15) . . ?
C7 C6 C9 107.98(16) . . ?
C8 C7 C6 122.77(17) . . ?
C8 C7 C10 129.92(15) . . ?
C6 C7 C10 107.30(15) . . ?
C7 C8 C2 114.97(15) . . ?
C7 C8 H8 122.5 . . ?
C2 C8 H8 122.5 . . ?
O3 C9 N2 124.6(2) . . ?
O3 C9 C6 128.61(18) . . ?
N2 C9 C6 106.73(14) . . ?
O4 C10 N2 125.6(2) . . ?
O4 C10 C7 128.00(17) . . ?
N2 C10 C7 106.40(15) . . ?
N1 C11 C12A 113.6(3) . . ?
N1 C11 C12 115.9(3) . . ?
N1 C11 H11A 108.3 . . ?
C12 C11 H11A 108.3 . . ?
N1 C11 H11B 108.3 . . ?
C12 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
N1 C11 H11C 108.8 . . ?
C12A C11 H11C 108.8 . . ?
N1 C11 H11D 108.8 . . ?
C12A C11 H11D 108.8 . . ?
H11C C11 H11D 107.7 . . ?
N2 C17 C18A 116.0(4) . . ?
N2 C17 C18 109.9(4) . . ?
N2 C17 H17A 109.7 . . ?
C18 C17 H17A 109.7 . . ?
N2 C17 H17B 109.7 . . ?
C18 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
N2 C17 H17C 108.3 . . ?
C18A C17 H17C 108.3 . . ?
N2 C17 H17D 108.3 . . ?
C18A C17 H17D 108.3 . . ?
H17C C17 H17D 107.4 . . ?
C13 C12 C11 110.3(5) . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 122.5(8) . . ?
C14 C13 H13A 106.7 . . ?
C12 C13 H13A 106.7 . . ?
C14 C13 H13B 106.7 . . ?
C12 C13 H13B 106.7 . . ?
H13A C13 H13B 106.6 . . ?
C13 C14 C15 128.5(10) . . ?
C13 C14 H14A 105.2 . . ?
C15 C14 H14A 105.2 . . ?
C13 C14 H14B 105.2 . . ?
C15 C14 H14B 105.2 . . ?
H14A C14 H14B 105.9 . . ?
C14 C15 C16 109.0(13) . . ?
C14 C15 H15A 109.9 . . ?
C16 C15 H15A 109.9 . . ?
C14 C15 H15B 109.9 . . ?
C16 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 110.0 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C17 C18 C19 114.8(7) . . ?
C17 C18 H18A 108.6 . . ?
C19 C18 H18A 108.6 . . ?
C17 C18 H18B 108.6 . . ?
C19 C18 H18B 108.6 . . ?
H18A C18 H18B 107.5 . . ?
C18 C19 C20 118.7(7) . . ?
C18 C19 H19A 107.6 . . ?
C20 C19 H19A 107.7 . . ?
C18 C19 H19B 107.6 . . ?
C20 C19 H19B 107.7 . . ?
H19A C19 H19B 107.1 . . ?
C19 C20 C21 105.9(7) . . ?
C19 C20 H20A 110.6 . . ?
C21 C20 H20A 110.6 . . ?
C19 C20 H20B 110.6 . . ?
C21 C20 H20B 110.6 . . ?
H20A C20 H20B 108.7 . . ?
C22 C21 C20 98.9(10) . . ?
C22 C21 H21A 112.0 . . ?
C20 C21 H21A 112.0 . . ?
C22 C21 H21B 112.0 . . ?
C20 C21 H21B 112.0 . . ?
H21A C21 H21B 109.7 . . ?
C21 C22 H22A 108.8 . . ?
C21 C22 H22B 109.7 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.9 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C13A C12A C11 116.2(6) . . ?
C13A C12A H12C 108.2 . . ?
C11 C12A H12C 108.2 . . ?
C13A C12A H12D 108.2 . . ?
C11 C12A H12D 108.2 . . ?
H12C C12A H12D 107.4 . . ?
C14A C13A C12A 128.1(8) . . ?
C14A C13A H13C 105.3 . . ?
C12A C13A H13C 105.3 . . ?
C14A C13A H13D 105.3 . . ?
C12A C13A H13D 105.3 . . ?
H13C C13A H13D 106.0 . . ?
C13A C14A C15A 121.5(9) . . ?
C13A C14A H14C 107.0 . . ?
C15A C14A H14C 107.0 . . ?
C13A C14A H14D 107.0 . . ?
C15A C14A H14D 107.0 . . ?
H14C C14A H14D 106.7 . . ?
C14A C15A C16A 100.1(13) . . ?
C14A C15A H15C 111.7 . . ?
C16A C15A H15C 111.8 . . ?
C14A C15A H15D 111.8 . . ?
C16A C15A H15D 111.8 . . ?
H15C C15A H15D 109.5 . . ?
C15A C16A H16D 108.8 . . ?
C15A C16A H16E 109.8 . . ?
H16D C16A H16E 109.5 . . ?
C15A C16A H16F 109.8 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
C17 C18A C19A 111.2(7) . . ?
C17 C18A H18C 109.4 . . ?
C19A C18A H18C 109.4 . . ?
C17 C18A H18D 109.4 . . ?
C19A C18A H18D 109.4 . . ?
H18C C18A H18D 108.0 . . ?
C18A C19A C20A 106.6(7) . . ?
C18A C19A H19C 110.4 . . ?
C20A C19A H19C 110.4 . . ?
C18A C19A H19D 110.4 . . ?
C20A C19A H19D 110.4 . . ?
H19C C19A H19D 108.6 . . ?
C21A C20A C19A 98.3(8) . . ?
C21A C20A H20C 112.1 . . ?
C19A C20A H20C 112.1 . . ?
C21A C20A H20D 112.1 . . ?
C19A C20A H20D 112.1 . . ?
H20C C20A H20D 109.7 . . ?
C22A C21A C20A 95.4(11) . . ?
C22A C21A H21C 112.7 . . ?
C20A C21A H21C 112.7 . . ?
C22A C21A H21D 112.7 . . ?
C20A C21A H21D 112.7 . . ?
H21C C21A H21D 110.1 . . ?
C21A C22A H22D 109.0 . . ?
C21A C22A H22E 108.8 . . ?
H22D C22A H22E 109.5 . . ?
C21A C22A H22F 110.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?

_refine_diff_density_max         0.182
_refine_diff_density_min         -0.163
_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_NDInC8_RT
_database_code_depnum_ccdc_archive 'CCDC 1998575'
loop_
_audit_author_name
_audit_author_address
'Agnieszka Czapik'
;Adam Mickiewicz University in Poznan
Poland
;
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2020-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H38 N2 O4'
_chemical_formula_sum            'C30 H38 N2 O4'
_chemical_formula_weight         490.62

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   4.77320(10)
_cell_length_b                   6.5321(2)
_cell_length_c                   22.7126(6)
_cell_angle_alpha                87.963(2)
_cell_angle_beta                 88.858(2)
_cell_angle_gamma                75.759(2)
_cell_volume                     685.92(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10193
_cell_measurement_theta_min      3.8770
_cell_measurement_theta_max      75.8520

_exptl_crystal_description       plank
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.625
_shelx_estimated_absorpt_T_min   0.835
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83896
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_reflns_number            4721
_diffrn_reflns_av_unetI/netI     0.0056
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         5.848
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_full        66.600
_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             4721
_reflns_number_gt                3558
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1042P)²+0.0555P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_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         4721
_refine_ls_number_parameters     165
_refine_ls_number_restraints     136
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1866
_refine_ls_wR_factor_gt          0.1766
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.055
_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
O1 O 0.0695(3) 0.5973(2) 0.59119(7) 0.0937(5) Uani 1 1 d . . . . .
O2 O 0.5004(4) 1.0421(2) 0.68290(6) 0.0993(5) Uani 1 1 d . . . . .
N1 N 0.2819(3) 0.8215(2) 0.63748(7) 0.0744(5) Uani 1 1 d . . . . .
C1 C 0.2073(4) 0.7308(3) 0.58736(9) 0.0719(5) Uani 1 1 d . . . . .
C2 C 0.3020(3) 0.8055(2) 0.52973(8) 0.0651(5) Uani 1 1 d . . . . .
C3 C 0.4573(3) 0.9635(2) 0.52757(7) 0.0615(4) Uani 1 1 d . . . . .
C4 C 0.5292(3) 1.0501(2) 0.57938(8) 0.0648(5) Uani 1 1 d . . . . .
C5 C 0.4396(4) 0.9749(3) 0.63719(9) 0.0745(5) Uani 1 1 d . . . . .
C6 C 0.2348(4) 0.7244(3) 0.47875(9) 0.0729(5) Uani 1 1 d . . . . .
H6 H 0.132389 0.620205 0.480436 0.088 Uiso 1 1 calc R U . . .
C7 C 0.6814(4) 1.2035(2) 0.57597(9) 0.0724(5) Uani 1 1 d . . . . .
H7 H 0.729112 1.259899 0.610325 0.087 Uiso 1 1 calc R U . . .
C8 C 0.1902(4) 0.7474(3) 0.69532(9) 0.0856(6) Uani 1 1 d . U . . .
H8A H 0.022287 0.691687 0.689887 0.103 Uiso 1 1 calc R U . . .
H8B H 0.133058 0.867040 0.720813 0.103 Uiso 1 1 calc R U . . .
C9 C 0.4217(4) 0.5801(3) 0.72514(9) 0.0866(6) Uani 1 1 d . U . . .
H9A H 0.510645 0.476323 0.696518 0.104 Uiso 1 1 calc R U . . .
H9B H 0.569974 0.644609 0.738901 0.104 Uiso 1 1 calc R U . . .
C10 C 0.3129(5) 0.4705(4) 0.77577(10) 0.1013(7) Uani 1 1 d . U . . .
H10A H 0.165528 0.405836 0.761672 0.122 Uiso 1 1 calc R U . . .
H10B H 0.221134 0.575476 0.803863 0.122 Uiso 1 1 calc R U . . .
C11 C 0.5390(5) 0.3023(4) 0.80762(10) 0.1045(7) Uani 1 1 d . U . . .
H11A H 0.656432 0.213437 0.778504 0.125 Uiso 1 1 calc R U . . .
H11B H 0.664648 0.371006 0.828343 0.125 Uiso 1 1 calc R U . . .
C12 C 0.4253(7) 0.1654(5) 0.85040(15) 0.1406(11) Uani 1 1 d . U . . .
H12A H 0.294139 0.100984 0.829904 0.169 Uiso 1 1 calc R U . . .
H12B H 0.313319 0.254082 0.880212 0.169 Uiso 1 1 calc R U . . .
C13 C 0.6499(7) -0.0092(6) 0.88122(16) 0.1485(12) Uani 1 1 d . U . . .
H13A H 0.775525 -0.087407 0.851282 0.178 Uiso 1 1 calc R U . . .
H13B H 0.767719 0.056612 0.905032 0.178 Uiso 1 1 calc R U . . .
C14 C 0.5465(10) -0.1570(7) 0.9181(2) 0.1922(18) Uani 1 1 d . U . . .
H14A H 0.432048 -0.225667 0.894305 0.231 Uiso 1 1 calc R U . . .
H14B H 0.419039 -0.079540 0.947879 0.231 Uiso 1 1 calc R U . . .
C15 C 0.7715(11) -0.3221(7) 0.9480(2) 0.206(2) Uani 1 1 d . U . . .
H15A H 0.886170 -0.410726 0.919084 0.309 Uiso 1 1 calc R U . . .
H15B H 0.681368 -0.406161 0.974102 0.309 Uiso 1 1 calc R U . . .
H15C H 0.893141 -0.256770 0.970132 0.309 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 C1 1.215(2) . ?
O2 C5 1.209(2) . ?
N1 C5 1.393(2) . ?
N1 C1 1.393(2) . ?
N1 C8 1.479(2) . ?
C1 C2 1.482(3) . ?
C2 C6 1.366(3) . ?
C2 C3 1.410(2) . ?
C3 C4 1.407(2) . ?
C3 C3 1.412(3) 2_676 ?
C4 C7 1.374(2) . ?
C4 C5 1.478(3) . ?
C6 C7 1.399(3) 2_676 ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.503(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.485(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.512(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.481(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.520(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.427(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.478(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C5 N1 C1 124.85(16) . . ?
C5 N1 C8 117.57(17) . . ?
C1 N1 C8 117.58(16) . . ?
O1 C1 N1 121.01(18) . . ?
O1 C1 C2 121.97(18) . . ?
N1 C1 C2 117.02(15) . . ?
C6 C2 C3 120.04(17) . . ?
C6 C2 C1 120.16(16) . . ?
C3 C2 C1 119.79(17) . . ?
C4 C3 C2 121.25(17) . . ?
C4 C3 C3 119.29(19) . 2_676 ?
C2 C3 C3 119.46(19) . 2_676 ?
C7 C4 C3 120.00(17) . . ?
C7 C4 C5 120.49(17) . . ?
C3 C4 C5 119.51(16) . . ?
O2 C5 N1 120.58(18) . . ?
O2 C5 C4 121.85(18) . . ?
N1 C5 C4 117.56(17) . . ?
C2 C6 C7 120.66(16) . 2_676 ?
C2 C6 H6 119.7 . . ?
C7 C6 H6 119.7 2_676 . ?
C4 C7 C6 120.54(17) . 2_676 ?
C4 C7 H7 119.7 . . ?
C6 C7 H7 119.7 2_676 . ?
N1 C8 C9 113.35(15) . . ?
N1 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
N1 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C8 113.46(17) . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 C11 115.36(19) . . ?
C9 C10 H10A 108.4 . . ?
C11 C10 H10A 108.4 . . ?
C9 C10 H10B 108.4 . . ?
C11 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C12 C11 C10 115.4(2) . . ?
C12 C11 H11A 108.4 . . ?
C10 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C10 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C11 C12 C13 116.0(3) . . ?
C11 C12 H12A 108.3 . . ?
C13 C12 H12A 108.3 . . ?
C11 C12 H12B 108.3 . . ?
C13 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
C14 C13 C12 117.3(3) . . ?
C14 C13 H13A 108.0 . . ?
C12 C13 H13A 108.0 . . ?
C14 C13 H13B 108.0 . . ?
C12 C13 H13B 108.0 . . ?
H13A C13 H13B 107.2 . . ?
C13 C14 C15 115.6(4) . . ?
C13 C14 H14A 108.4 . . ?
C15 C14 H14A 108.4 . . ?
C13 C14 H14B 108.4 . . ?
C15 C14 H14B 108.4 . . ?
H14A C14 H14B 107.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_refine_diff_density_max         0.166
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_NDInC8_130K
_database_code_depnum_ccdc_archive 'CCDC 1998576'
loop_
_audit_author_name
_audit_author_address
'Agnieszka Czapik'
;Adam Mickiewicz University in Poznan
Poland
;
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2020-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H38 N2 O4'
_chemical_formula_sum            'C30 H38 N2 O4'
_chemical_formula_weight         490.62

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   4.6210(2)
_cell_length_b                   6.6424(2)
_cell_length_c                   21.5809(10)
_cell_angle_alpha                90.464(3)
_cell_angle_beta                 91.624(4)
_cell_angle_gamma                104.599(3)
_cell_volume                     640.69(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    1073
_cell_measurement_theta_min      4.0830
_cell_measurement_theta_max      72.8370

_exptl_crystal_description       plank
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.669
_shelx_estimated_absorpt_T_min   0.731
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80527
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_reflns_number            8306
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.099
_diffrn_reflns_theta_max         70.027
_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             2433
_reflns_number_gt                2115
_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 1.171.40.57a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0916P)²+0.1919P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_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         2433
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1469
_refine_ls_wR_factor_gt          0.1384
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.5154(2) 1.06227(15) 0.69364(4) 0.0315(3) Uani 1 1 d . . . . .
O2 O 0.9349(2) 0.60441(15) 0.59452(5) 0.0315(3) Uani 1 1 d . . . . .
N1 N 0.7280(2) 0.83535(17) 0.64439(5) 0.0229(3) Uani 1 1 d . . . . .
C1 C 0.5705(3) 0.9895(2) 0.64494(6) 0.0234(3) Uani 1 1 d . . . . .
C2 C 0.4767(3) 1.05869(19) 0.58401(6) 0.0210(3) Uani 1 1 d . . . . .
C3 C 0.5439(3) 0.96588(19) 0.52893(6) 0.0195(3) Uani 1 1 d . . . . .
C4 C 0.6984(3) 0.80803(19) 0.53068(6) 0.0212(3) Uani 1 1 d . . . . .
C5 C 0.7973(3) 0.7385(2) 0.59114(6) 0.0232(3) Uani 1 1 d . . . . .
C6 C 0.7627(3) 0.7204(2) 0.47631(6) 0.0234(3) Uani 1 1 d . . . . .
H6 H 0.866923 0.614161 0.477710 0.028 Uiso 1 1 calc R U . . .
C7 C 0.3253(3) 1.2124(2) 0.58127(6) 0.0239(3) Uani 1 1 d . . . . .
H7 H 0.279860 1.273594 0.618510 0.029 Uiso 1 1 calc R U . . .
C8 C 0.8257(3) 0.7676(2) 0.70502(6) 0.0259(3) Uani 1 1 d . . . . .
H8A H 0.898527 0.891087 0.732521 0.031 Uiso 1 1 calc R U . . .
H8B H 0.994990 0.704045 0.698675 0.031 Uiso 1 1 calc R U . . .
C9 C 0.5771(3) 0.6114(2) 0.73686(6) 0.0265(3) Uani 1 1 d . . . . .
H9A H 0.447136 0.686527 0.757964 0.032 Uiso 1 1 calc R U . . .
H9B H 0.452831 0.516393 0.705297 0.032 Uiso 1 1 calc R U . . .
C10 C 0.7039(3) 0.4846(2) 0.78412(6) 0.0258(3) Uani 1 1 d . . . . .
H10A H 0.832669 0.580773 0.814809 0.031 Uiso 1 1 calc R U . . .
H10B H 0.830917 0.408165 0.762603 0.031 Uiso 1 1 calc R U . . .
C11 C 0.4625(3) 0.3293(2) 0.81825(6) 0.0261(3) Uani 1 1 d . . . . .
H11A H 0.362578 0.406256 0.846629 0.031 Uiso 1 1 calc R U . . .
H11B H 0.309926 0.252203 0.787694 0.031 Uiso 1 1 calc R U . . .
C12 C 0.5869(3) 0.1744(2) 0.85542(6) 0.0281(3) Uani 1 1 d . . . . .
H12A H 0.738188 0.251743 0.886162 0.034 Uiso 1 1 calc R U . . .
H12B H 0.689056 0.098933 0.827026 0.034 Uiso 1 1 calc R U . . .
C13 C 0.3480(3) 0.0165(2) 0.88929(7) 0.0295(4) Uani 1 1 d . . . . .
H13A H 0.259530 0.090606 0.920663 0.035 Uiso 1 1 calc R U . . .
H13B H 0.186632 -0.051456 0.859182 0.035 Uiso 1 1 calc R U . . .
C14 C 0.4695(4) -0.1504(2) 0.92131(7) 0.0329(4) Uani 1 1 d . . . . .
H14A H 0.630005 -0.082492 0.951621 0.040 Uiso 1 1 calc R U . . .
H14B H 0.559266 -0.223852 0.889982 0.040 Uiso 1 1 calc R U . . .
C15 C 0.2305(4) -0.3090(2) 0.95482(8) 0.0381(4) Uani 1 1 d . . . . .
H15A H 0.071684 -0.377965 0.925029 0.057 Uiso 1 1 calc R U . . .
H15B H 0.145696 -0.238121 0.986979 0.057 Uiso 1 1 calc R U . . .
H15C H 0.320412 -0.413041 0.973971 0.057 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 C1 1.2131(16) . ?
O2 C5 1.2193(17) . ?
N1 C5 1.3962(18) . ?
N1 C1 1.3982(17) . ?
N1 C8 1.4822(16) . ?
C1 C2 1.4853(18) . ?
C2 C7 1.3763(19) . ?
C2 C3 1.4125(19) . ?
C3 C4 1.4094(19) . ?
C3 C3 1.415(3) 2_676 ?
C4 C6 1.3781(19) . ?
C4 C5 1.4857(19) . ?
C6 C7 1.407(2) 2_676 ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.5245(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5235(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5264(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5223(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5257(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5246(19) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.525(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C1 125.02(11) . . ?
C5 N1 C8 117.47(11) . . ?
C1 N1 C8 117.50(11) . . ?
O1 C1 N1 120.47(12) . . ?
O1 C1 C2 122.30(12) . . ?
N1 C1 C2 117.23(11) . . ?
C7 C2 C3 120.23(12) . . ?
C7 C2 C1 120.16(12) . . ?
C3 C2 C1 119.61(12) . . ?
C4 C3 C2 121.16(12) . . ?
C4 C3 C3 119.63(15) . 2_676 ?
C2 C3 C3 119.20(15) . 2_676 ?
C6 C4 C3 120.11(12) . . ?
C6 C4 C5 119.85(12) . . ?
C3 C4 C5 120.03(12) . . ?
O2 C5 N1 121.12(12) . . ?
O2 C5 C4 121.96(12) . . ?
N1 C5 C4 116.92(11) . . ?
C4 C6 C7 120.36(12) . 2_676 ?
C4 C6 H6 119.8 . . ?
C7 C6 H6 119.8 2_676 . ?
C2 C7 C6 120.45(12) . 2_676 ?
C2 C7 H7 119.8 . . ?
C6 C7 H7 119.8 2_676 . ?
N1 C8 C9 112.99(11) . . ?
N1 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C8 111.36(11) . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 C11 113.20(11) . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C10 112.73(11) . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 C13 113.42(12) . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C12 113.04(12) . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 C15 113.06(13) . . ?
C13 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_PIRnC6_130K
_database_code_depnum_ccdc_archive 'CCDC 1998577'
loop_
_audit_author_name
_audit_author_address
'Agnieszka Czapik'
;Adam Mickiewicz University in Poznan
Poland
;
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2020-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C11 H14 N O2)'
_chemical_formula_sum            'C22 H28 N2 O4'
_chemical_formula_weight         384.46

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   4.6995(2)
_cell_length_b                   13.0120(4)
_cell_length_c                   16.5659(4)
_cell_angle_alpha                81.879(2)
_cell_angle_beta                 86.016(2)
_cell_angle_gamma                89.894(3)
_cell_volume                     1000.39(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    3420
_cell_measurement_theta_min      2.6780
_cell_measurement_theta_max      76.0350

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             412
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.711
_shelx_estimated_absorpt_T_min   0.764
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.74390
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_reflns_number            15546
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.701
_diffrn_reflns_theta_max         76.472
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4109
_reflns_number_gt                3473
_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 1.171.40.57a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0608P)²+0.1823P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_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         4109
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1105
_refine_ls_wR_factor_gt          0.1042
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.002
_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
O1A O 1.2139(2) 0.61897(7) 0.68274(5) 0.0322(2) Uani 1 1 d . . . . .
O2A O 0.48534(19) 0.38811(7) 0.67529(5) 0.0324(2) Uani 1 1 d . . . . .
N1A N 0.8336(2) 0.50272(8) 0.70060(6) 0.0262(2) Uani 1 1 d . . . . .
C1A C 1.0551(3) 0.56117(9) 0.65632(7) 0.0259(2) Uani 1 1 d . . . . .
C2A C 1.0515(2) 0.53696(9) 0.57049(7) 0.0243(2) Uani 1 1 d . . . . .
C3A C 0.8359(2) 0.46439(9) 0.56897(7) 0.0245(2) Uani 1 1 d . . . . .
C4A C 0.6905(3) 0.44350(9) 0.65268(7) 0.0260(3) Uani 1 1 d . . . . .
C5A C 0.7763(3) 0.42453(9) 0.49833(7) 0.0260(2) Uani 1 1 d . . . . .
H5A H 0.629228 0.374825 0.497367 0.031 Uiso 1 1 calc R U . . .
C6A C 0.7493(3) 0.50752(10) 0.78685(7) 0.0290(3) Uani 1 1 d . . . . .
H6AA H 0.538815 0.511326 0.793988 0.035 Uiso 1 1 calc R U . . .
H6AB H 0.829150 0.571673 0.802455 0.035 Uiso 1 1 calc R U . . .
C7A C 0.8508(3) 0.41408(9) 0.84369(7) 0.0270(3) Uani 1 1 d . . . . .
H7AA H 0.783268 0.349395 0.825897 0.032 Uiso 1 1 calc R U . . .
H7AB H 1.061908 0.413283 0.840343 0.032 Uiso 1 1 calc R U . . .
C8A C 0.7392(3) 0.41787(10) 0.93175(7) 0.0285(3) Uani 1 1 d . . . . .
H8AA H 0.528208 0.419623 0.934409 0.034 Uiso 1 1 calc R U . . .
H8AB H 0.807060 0.482879 0.948962 0.034 Uiso 1 1 calc R U . . .
C9A C 0.8330(3) 0.32583(10) 0.99156(7) 0.0287(3) Uani 1 1 d . . . . .
H9AA H 0.763742 0.260778 0.974739 0.034 Uiso 1 1 calc R U . . .
H9AB H 1.043972 0.323713 0.988745 0.034 Uiso 1 1 calc R U . . .
C10A C 0.7218(3) 0.33091(10) 1.07963(7) 0.0322(3) Uani 1 1 d . . . . .
H10A H 0.510703 0.331920 1.082400 0.039 Uiso 1 1 calc R U . . .
H10B H 0.787895 0.396727 1.095874 0.039 Uiso 1 1 calc R U . . .
C11A C 0.8177(3) 0.24048(11) 1.14066(8) 0.0391(3) Uani 1 1 d . . . . .
H11A H 0.736805 0.175499 1.128448 0.059 Uiso 1 1 calc R U . . .
H11B H 0.751302 0.251295 1.196210 0.059 Uiso 1 1 calc R U . . .
H11C H 1.026333 0.236650 1.136465 0.059 Uiso 1 1 calc R U . . .
O1B O -0.3471(2) 0.01206(7) 0.79994(5) 0.0327(2) Uani 1 1 d . . . . .
O2B O 0.3788(2) 0.21779(7) 0.85895(6) 0.0329(2) Uani 1 1 d . . . . .
N1B N 0.0183(2) 0.12872(8) 0.80891(6) 0.0265(2) Uani 1 1 d . . . . .
C1B C -0.1671(3) 0.04629(9) 0.83790(7) 0.0257(2) Uani 1 1 d . . . . .
C2B C -0.1000(2) 0.01204(9) 0.92432(7) 0.0248(2) Uani 1 1 d . . . . .
C3B C 0.1156(2) 0.07587(9) 0.94267(7) 0.0248(2) Uani 1 1 d . . . . .
C4B C 0.1965(3) 0.15090(9) 0.86772(7) 0.0262(3) Uani 1 1 d . . . . .
C5B C 0.2238(3) 0.06664(9) 1.01907(7) 0.0264(3) Uani 1 1 d . . . . .
H5B H 0.370728 0.110628 1.031615 0.032 Uiso 1 1 calc R U . . .
C6B C 0.0186(3) 0.18626(10) 0.72657(7) 0.0290(3) Uani 1 1 d . . . . .
H6BA H 0.118111 0.253530 0.725242 0.035 Uiso 1 1 calc R U . . .
H6BB H -0.180839 0.201097 0.713250 0.035 Uiso 1 1 calc R U . . .
C7B C 0.1630(3) 0.12774(10) 0.66187(8) 0.0317(3) Uani 1 1 d . . . . .
H7BA H 0.366547 0.117323 0.672412 0.038 Uiso 1 1 calc R U . . .
H7BB H 0.072051 0.058575 0.665086 0.038 Uiso 1 1 calc R U . . .
C8B C 0.1400(3) 0.18744(10) 0.57683(8) 0.0326(3) Uani 1 1 d . . . . .
H8BA H 0.230159 0.256597 0.574497 0.039 Uiso 1 1 calc R U . . .
H8BB H -0.064226 0.198360 0.567343 0.039 Uiso 1 1 calc R U . . .
C9B C 0.2789(3) 0.13361(11) 0.50832(8) 0.0364(3) Uani 1 1 d . . . . .
H9BA H 0.485507 0.126350 0.515800 0.044 Uiso 1 1 calc R U . . .
H9BB H 0.196425 0.062966 0.512296 0.044 Uiso 1 1 calc R U . . .
C10B C 0.2394(4) 0.19165(12) 0.42357(9) 0.0422(3) Uani 1 1 d . . . . .
H10C H 0.326401 0.261625 0.419149 0.051 Uiso 1 1 calc R U . . .
H10D H 0.032800 0.200594 0.416705 0.051 Uiso 1 1 calc R U . . .
C11B C 0.3711(4) 0.13671(15) 0.35478(10) 0.0570(5) Uani 1 1 d . . . . .
H11D H 0.327584 0.175344 0.301957 0.085 Uiso 1 1 calc R U . . .
H11E H 0.292075 0.066245 0.360019 0.085 Uiso 1 1 calc R U . . .
H11F H 0.578358 0.133211 0.358124 0.085 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
O1A C1A 1.2061(15) . ?
O2A C4A 1.2105(15) . ?
N1A C4A 1.3874(15) . ?
N1A C1A 1.3926(15) . ?
N1A C6A 1.4658(15) . ?
C1A C2A 1.5004(16) . ?
C2A C5A 1.3845(16) 2_766 ?
C2A C3A 1.3904(16) . ?
C3A C5A 1.3908(16) . ?
C3A C4A 1.4921(16) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.5262(17) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C7A C8A 1.5229(16) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C8A C9A 1.5276(17) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C9A C10A 1.5255(17) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C10A C11A 1.5281(19) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
O1B C1B 1.2100(15) . ?
O2B C4B 1.2092(15) . ?
N1B C4B 1.3883(15) . ?
N1B C1B 1.3929(15) . ?
N1B C6B 1.4603(15) . ?
C1B C2B 1.4932(17) . ?
C2B C5B 1.3860(17) 2_557 ?
C2B C3B 1.3877(16) . ?
C3B C5B 1.3862(17) . ?
C3B C4B 1.4941(17) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.5221(17) . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
C7B C8B 1.5204(17) . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C8B C9B 1.5247(18) . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C9B C10B 1.521(2) . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C10B C11B 1.524(2) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4A N1A C1A 112.35(10) . . ?
C4A N1A C6A 123.52(10) . . ?
C1A N1A C6A 124.04(10) . . ?
O1A C1A N1A 126.25(11) . . ?
O1A C1A C2A 128.11(11) . . ?
N1A C1A C2A 105.64(10) . . ?
C5A C2A C3A 122.62(11) 2_766 . ?
C5A C2A C1A 129.47(11) 2_766 . ?
C3A C2A C1A 107.91(10) . . ?
C2A C3A C5A 122.72(11) . . ?
C2A C3A C4A 107.84(10) . . ?
C5A C3A C4A 129.42(11) . . ?
O2A C4A N1A 125.88(11) . . ?
O2A C4A C3A 127.89(11) . . ?
N1A C4A C3A 106.22(10) . . ?
C2A C5A C3A 114.67(11) 2_766 . ?
C2A C5A H5A 122.7 2_766 . ?
C3A C5A H5A 122.7 . . ?
N1A C6A C7A 112.77(10) . . ?
N1A C6A H6AA 109.0 . . ?
C7A C6A H6AA 109.0 . . ?
N1A C6A H6AB 109.0 . . ?
C7A C6A H6AB 109.0 . . ?
H6AA C6A H6AB 107.8 . . ?
C8A C7A C6A 111.05(10) . . ?
C8A C7A H7AA 109.4 . . ?
C6A C7A H7AA 109.4 . . ?
C8A C7A H7AB 109.4 . . ?
C6A C7A H7AB 109.4 . . ?
H7AA C7A H7AB 108.0 . . ?
C7A C8A C9A 113.43(11) . . ?
C7A C8A H8AA 108.9 . . ?
C9A C8A H8AA 108.9 . . ?
C7A C8A H8AB 108.9 . . ?
C9A C8A H8AB 108.9 . . ?
H8AA C8A H8AB 107.7 . . ?
C10A C9A C8A 112.94(11) . . ?
C10A C9A H9AA 109.0 . . ?
C8A C9A H9AA 109.0 . . ?
C10A C9A H9AB 109.0 . . ?
C8A C9A H9AB 109.0 . . ?
H9AA C9A H9AB 107.8 . . ?
C9A C10A C11A 113.75(11) . . ?
C9A C10A H10A 108.8 . . ?
C11A C10A H10A 108.8 . . ?
C9A C10A H10B 108.8 . . ?
C11A C10A H10B 108.8 . . ?
H10A C10A H10B 107.7 . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C4B N1B C1B 112.26(10) . . ?
C4B N1B C6B 124.30(10) . . ?
C1B N1B C6B 123.43(10) . . ?
O1B C1B N1B 125.98(11) . . ?
O1B C1B C2B 128.17(11) . . ?
N1B C1B C2B 105.84(10) . . ?
C5B C2B C3B 122.66(11) 2_557 . ?
C5B C2B C1B 129.32(11) 2_557 . ?
C3B C2B C1B 108.00(10) . . ?
C5B C3B C2B 122.86(11) . . ?
C5B C3B C4B 129.22(11) . . ?
C2B C3B C4B 107.92(10) . . ?
O2B C4B N1B 126.23(11) . . ?
O2B C4B C3B 127.80(11) . . ?
N1B C4B C3B 105.97(10) . . ?
C2B C5B C3B 114.48(11) 2_557 . ?
C2B C5B H5B 122.8 2_557 . ?
C3B C5B H5B 122.8 . . ?
N1B C6B C7B 112.83(10) . . ?
N1B C6B H6BA 109.0 . . ?
C7B C6B H6BA 109.0 . . ?
N1B C6B H6BB 109.0 . . ?
C7B C6B H6BB 109.0 . . ?
H6BA C6B H6BB 107.8 . . ?
C8B C7B C6B 110.80(11) . . ?
C8B C7B H7BA 109.5 . . ?
C6B C7B H7BA 109.5 . . ?
C8B C7B H7BB 109.5 . . ?
C6B C7B H7BB 109.5 . . ?
H7BA C7B H7BB 108.1 . . ?
C7B C8B C9B 114.05(11) . . ?
C7B C8B H8BA 108.7 . . ?
C9B C8B H8BA 108.7 . . ?
C7B C8B H8BB 108.7 . . ?
C9B C8B H8BB 108.7 . . ?
H8BA C8B H8BB 107.6 . . ?
C10B C9B C8B 113.19(12) . . ?
C10B C9B H9BA 108.9 . . ?
C8B C9B H9BA 108.9 . . ?
C10B C9B H9BB 108.9 . . ?
C8B C9B H9BB 108.9 . . ?
H9BA C9B H9BB 107.8 . . ?
C9B C10B C11B 113.41(14) . . ?
C9B C10B H10C 108.9 . . ?
C11B C10B H10C 108.9 . . ?
C9B C10B H10D 108.9 . . ?
C11B C10B H10D 108.9 . . ?
H10C C10B H10D 107.7 . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.042

