# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_CP1
_database_code_depnum_ccdc_archive 'CCDC 1975157'
loop_
_audit_author_name
_audit_author_address
'shuangyan wu'
;Shenyang University of Chemical Technology
China
;
_audit_update_record             
;
2020-01-02 deposited with the CCDC.	2020-02-24 downloaded from the CCDC.
;
_audit_creation_date             2019-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '1(C45 H42 La1 N9 O9)'
_chemical_formula_sum            'C45 H42 La N9 O9'
_chemical_formula_weight         991.79
_chemical_melting_point          ?
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'
La La -0.2871 2.4523 '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'

_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.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   14.564(8)
_cell_length_b                   14.564(8)
_cell_length_c                   41.89(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     7695(11)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    3287
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.83
_cell_measurement_theta_min      2.51
_shelx_estimated_absorpt_T_max   0.856
_shelx_estimated_absorpt_T_min   0.828
_exptl_absorpt_coefficient_mu    0.890
_exptl_absorpt_correction_T_max  0.855
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             3024
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            16316
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.236
_diffrn_reflns_theta_max         25.236
_diffrn_reflns_theta_min         1.686
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2571
_reflns_number_total             3089
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3089
_refine_ls_number_restraints     134
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0711P)²+8.2720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1240
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed U13: La1(0)
 Fixed U23: La1(0)
 Fixed Uiso: H13A(0.124) H14A(0.227) H14B(0.227) H14C(0.227) H15A(0.266)
 H15B(0.266) H15C(0.266) H13B(0.14) H14D(0.293) H14E(0.293) H14F(0.293)
 H15D(0.235) H15E(0.235) H15F(0.235)
 Fixed X: H3(0.628813) H4(0.56449) H5(0.406067) H6(0.311514) H8(0.460891)
 H9(0.304282) H12(0.130241) H13A(0.488193) H14A(0.368236) H14B(0.324776)
 H14C(0.433506) H15A(0.50716) H15B(0.38765) H15C(0.41785) H13B(0.548524)
 H14D(0.504557) H14E(0.382867) H14F(0.462307) H15D(0.356765) H15E(0.471785)
 H15F(0.409615) La1(0.666667)
 Fixed Y: H3(0.005862) H4(-0.151336) H5(-0.219895) H6(-0.131892) H8(0.198377)
 H9(0.220131) H12(0.176023) H13A(0.169165) H14A(0.067686) H14B(0.122856)
 H14C(0.129706) H15A(0.372419) H15B(0.302259) H15C(0.353229) H13B(0.440938)
 H14D(0.4606) H14E(0.3993) H14F(0.48664) H15D(0.22144) H15E(0.23945)
 H15F(0.19557) La1(0.333333)
 Fixed Z: H3(0.068507) H4(0.04203) H5(0.014821) H6(0.015454) H8(0.036283)
 H9(0.031764) H12(0.040551) H13A(0.161767) H14A(0.200946) H14B(0.223646)
 H14C(0.231116) H15A(0.214726) H15B(0.224356) H15C(0.190246) H13B(0.157409)
 H14D(0.226831) H14E(0.219221) H14F(0.195691) H15D(0.21838) H15E(0.2219)
 H15F(0.18979)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5569(3) 0.1322(3) 0.07828(10) 0.0478(10) Uani 1 1 d . . . . .
C2 C 0.5074(3) 0.0302(3) 0.05960(11) 0.0498(10) Uani 1 1 d . . . . .
C3 C 0.5637(4) -0.0228(4) 0.05820(14) 0.0667(13) Uani 1 1 d . . . . .
H3 H 0.628813 0.005862 0.068507 0.14(3) Uiso 1 1 calc R . . . .
C4 C 0.5263(4) -0.1158(4) 0.04214(15) 0.0805(16) Uani 1 1 d . . . . .
H4 H 0.564490 -0.151336 0.042030 0.11(2) Uiso 1 1 calc R . . . .
C5 C 0.4318(4) -0.1567(4) 0.02607(15) 0.0745(15) Uani 1 1 d . . . . .
H5 H 0.406067 -0.219895 0.014821 0.074(15) Uiso 1 1 calc R . . . .
C6 C 0.3752(4) -0.1047(4) 0.02655(12) 0.0624(12) Uani 1 1 d . . . . .
H6 H 0.311514 -0.131892 0.015454 0.088(18) Uiso 1 1 calc R . . . .
C7 C 0.4131(3) -0.0123(3) 0.04353(10) 0.0482(10) Uani 1 1 d . . . . .
C8 C 0.3903(3) 0.1452(3) 0.03764(11) 0.0526(10) Uani 1 1 d . . . . .
H8 H 0.460891 0.198377 0.036283 0.066(14) Uiso 1 1 calc R . . . .
C9 C 0.3048(3) 0.1574(3) 0.03532(11) 0.0527(10) Uani 1 1 d . . . . .
H9 H 0.304282 0.220131 0.031764 0.078(16) Uiso 1 1 calc R . . . .
C10 C 0.2171(3) 0.0563(3) 0.03934(10) 0.0448(9) Uani 1 1 d . . . . .
C11 C 0.1062(3) 0.0273(3) 0.04015(9) 0.0448(9) Uani 1 1 d . . . . .
C12 C 0.0776(3) 0.1050(3) 0.04032(10) 0.0463(9) Uani 1 1 d . . . . .
H12 H 0.130241 0.176023 0.040551 0.053(12) Uiso 1 1 calc R . . . .
N3A N 0.4414(6) 0.2279(8) 0.19536(18) 0.123(3) Uani 0.628(6) 1 d D U . A 1
C13A C 0.4894(5) 0.2310(8) 0.16811(18) 0.104(3) Uani 0.628(6) 1 d D U . A 1
H13A H 0.488193 0.169165 0.161767 0.124 Uiso 0.628(6) 1 calc R . . A 1
C14A C 0.3875(8) 0.1280(11) 0.2144(3) 0.151(5) Uani 0.628(6) 1 d D U . A 1
H14A H 0.368236 0.067686 0.200946 0.227 Uiso 0.628(6) 1 d R . . A 1
H14B H 0.324776 0.122856 0.223646 0.227 Uiso 0.628(6) 1 d R . . A 1
H14C H 0.433506 0.129706 0.231116 0.227 Uiso 0.628(6) 1 d R . . A 1
C15A C 0.4376(8) 0.3220(10) 0.2071(3) 0.177(5) Uani 0.628(6) 1 d D U . A 1
H15A H 0.507160 0.372419 0.214726 0.266 Uiso 0.628(6) 1 d R . . A 1
H15B H 0.387650 0.302259 0.224356 0.266 Uiso 0.628(6) 1 d R . . A 1
H15C H 0.417850 0.353229 0.190246 0.266 Uiso 0.628(6) 1 d R . . A 1
N3B N 0.4658(8) 0.3471(13) 0.1937(3) 0.146(4) Uani 0.372(6) 1 d D U . A 2
C13B C 0.5209(7) 0.3728(13) 0.1656(3) 0.116(4) Uani 0.372(6) 1 d D U . A 2
H13B H 0.548524 0.440938 0.157409 0.140 Uiso 0.372(6) 1 calc R . . A 2
C14B C 0.4526(14) 0.4313(18) 0.2101(4) 0.195(8) Uani 0.372(6) 1 d D U . A 2
H14D H 0.504557 0.460600 0.226831 0.293 Uiso 0.372(6) 1 d R . . A 2
H14E H 0.382867 0.399300 0.219221 0.293 Uiso 0.372(6) 1 d R . . A 2
H14F H 0.462307 0.486640 0.195691 0.293 Uiso 0.372(6) 1 d R . . A 2
C15B C 0.4223(9) 0.2425(15) 0.2074(4) 0.157(6) Uani 0.372(6) 1 d D U . A 2
H15D H 0.356765 0.221440 0.218380 0.235 Uiso 0.372(6) 1 d R . . A 2
H15E H 0.471785 0.239450 0.221900 0.235 Uiso 0.372(6) 1 d R . . A 2
H15F H 0.409615 0.195570 0.189790 0.235 Uiso 0.372(6) 1 d R . . A 2
N1 N 0.2468(3) -0.0152(3) 0.04308(8) 0.0484(8) Uani 1 1 d . . . . .
N2 N 0.3539(2) 0.0412(2) 0.04230(8) 0.0468(8) Uani 1 1 d . . . . .
O1 O 0.5107(3) 0.1440(3) 0.10093(8) 0.0683(9) Uani 1 1 d . . . . .
O2 O 0.5553(3) 0.3536(3) 0.06988(9) 0.0796(11) Uani 1 1 d . . . . .
O3 O 0.5344(3) 0.3071(4) 0.15094(9) 0.0925(12) Uani 1 1 d D U . . .
La1 La 0.666667 0.333333 0.11027(2) 0.04461(18) Uani 1 3 d S T P A .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.506(6) . ?
C1 O1 1.224(5) . ?
C1 O2 1.236(5) 2_655 ?
C1 La1 2.872(4) . ?
C2 C3 1.380(6) . ?
C2 C7 1.368(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.359(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.371(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.371(6) . ?
C7 N2 1.424(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.346(6) . ?
C8 N2 1.344(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.395(6) . ?
C10 C11 1.452(5) . ?
C10 N1 1.322(5) . ?
C11 C12 1.388(6) . ?
C11 C12 1.378(6) 3 ?
C12 H12 0.9300 . ?
N3A C13A 1.327(10) . ?
N3A C14A 1.493(12) . ?
N3A C15A 1.483(13) . ?
C13A H13A 0.9300 . ?
C13A O3 1.205(9) . ?
C14A H14A 0.9601 . ?
C14A H14B 0.9602 . ?
C14A H14C 0.9600 . ?
C15A H15A 0.9601 . ?
C15A H15B 0.9606 . ?
C15A H15C 0.9599 . ?
N3B C13B 1.368(13) . ?
N3B C14B 1.499(15) . ?
N3B C15B 1.444(15) . ?
C13B H13B 0.9300 . ?
C13B O3 1.233(13) . ?
C14B H14D 0.9598 . ?
C14B H14E 0.9599 . ?
C14B H14F 0.9600 . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9598 . ?
C15B H15F 0.9604 . ?
N1 N2 1.352(5) . ?
O1 La1 2.580(4) . ?
O2 La1 2.461(3) . ?
O3 La1 2.454(4) . ?

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
C2 C1 La1 175.1(3) . . ?
O1 C1 C2 121.0(4) . . ?
O1 C1 O2 122.4(4) . 2_655 ?
O1 C1 La1 63.9(2) . . ?
O2 C1 C2 116.6(4) 2_655 . ?
O2 C1 La1 58.4(2) 2_655 . ?
C3 C2 C1 116.7(4) . . ?
C7 C2 C1 125.4(4) . . ?
C7 C2 C3 117.9(4) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.7(5) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.4(5) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(5) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 120.3 . . ?
C5 C6 C7 119.4(5) . . ?
C7 C6 H6 120.3 . . ?
C2 C7 C6 121.4(4) . . ?
C2 C7 N2 121.1(4) . . ?
C6 C7 N2 117.5(4) . . ?
C9 C8 H8 126.6 . . ?
N2 C8 H8 126.6 . . ?
N2 C8 C9 106.8(4) . . ?
C8 C9 H9 127.1 . . ?
C8 C9 C10 105.7(4) . . ?
C10 C9 H9 127.1 . . ?
C9 C10 C11 127.5(4) . . ?
N1 C10 C9 111.0(3) . . ?
N1 C10 C11 121.5(3) . . ?
C12 C11 C10 120.8(4) 3 . ?
C12 C11 C10 120.5(4) . . ?
C12 C11 C12 118.7(4) 3 . ?
C11 C12 C11 121.2(4) 2 . ?
C11 C12 H12 119.4 2 . ?
C11 C12 H12 119.4 . . ?
C13A N3A C14A 120.2(9) . . ?
C13A N3A C15A 121.2(8) . . ?
C15A N3A C14A 118.6(9) . . ?
N3A C13A H13A 117.3 . . ?
O3 C13A N3A 125.4(9) . . ?
O3 C13A H13A 117.3 . . ?
N3A C14A H14A 110.4 . . ?
N3A C14A H14B 107.9 . . ?
N3A C14A H14C 110.1 . . ?
H14A C14A H14B 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.4 . . ?
N3A C15A H15A 107.7 . . ?
N3A C15A H15B 110.2 . . ?
N3A C15A H15C 110.5 . . ?
H15A C15A H15B 109.4 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C13B N3B C14B 117.9(11) . . ?
C13B N3B C15B 121.3(10) . . ?
C15B N3B C14B 120.8(12) . . ?
N3B C13B H13B 119.5 . . ?
O3 C13B N3B 121.1(13) . . ?
O3 C13B H13B 119.5 . . ?
N3B C14B H14D 107.6 . . ?
N3B C14B H14E 108.8 . . ?
N3B C14B H14F 111.9 . . ?
H14D C14B H14E 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.4 . . ?
N3B C15B H15D 111.7 . . ?
N3B C15B H15E 110.9 . . ?
N3B C15B H15F 105.8 . . ?
H15D C15B H15E 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C10 N1 N2 104.5(3) . . ?
C8 N2 C7 128.0(3) . . ?
C8 N2 N1 112.0(3) . . ?
N1 N2 C7 119.8(3) . . ?
C1 O1 La1 90.8(3) . . ?
C1 O2 La1 96.2(3) 3_665 . ?
C13A O3 La1 125.5(5) . . ?
C13B O3 La1 130.0(7) . . ?
C1 La1 C1 99.98(11) . 2_655 ?
C1 La1 C1 99.98(11) 2_655 3_665 ?
C1 La1 C1 99.98(11) . 3_665 ?
O1 La1 C1 96.82(12) 3_665 2_655 ?
O1 La1 C1 25.23(10) . . ?
O1 La1 C1 125.00(11) 3_665 . ?
O1 La1 C1 125.00(11) . 2_655 ?
O1 La1 C1 25.23(10) 3_665 3_665 ?
O1 La1 C1 96.82(12) . 3_665 ?
O1 La1 C1 25.23(10) 2_655 2_655 ?
O1 La1 C1 96.82(12) 2_655 . ?
O1 La1 C1 125.00(11) 2_655 3_665 ?
O1 La1 O1 117.74(4) . 3_665 ?
O1 La1 O1 117.74(4) 2_655 . ?
O1 La1 O1 117.74(4) 2_655 3_665 ?
O2 La1 C1 74.77(12) 2_655 2_655 ?
O2 La1 C1 74.77(12) . . ?
O2 La1 C1 101.78(14) . 2_655 ?
O2 La1 C1 101.78(14) 2_655 3_665 ?
O2 La1 C1 101.78(14) 3_665 . ?
O2 La1 C1 25.33(11) 3_665 2_655 ?
O2 La1 C1 25.33(11) 2_655 . ?
O2 La1 C1 25.33(11) . 3_665 ?
O2 La1 C1 74.77(12) 3_665 3_665 ?
O2 La1 O1 75.11(11) . . ?
O2 La1 O1 125.42(13) 3_665 . ?
O2 La1 O1 50.56(10) 2_655 . ?
O2 La1 O1 50.56(10) 3_665 2_655 ?
O2 La1 O1 50.56(10) . 3_665 ?
O2 La1 O1 75.11(11) 2_655 2_655 ?
O2 La1 O1 125.43(13) . 2_655 ?
O2 La1 O1 125.42(13) 2_655 3_665 ?
O2 La1 O1 75.11(11) 3_665 3_665 ?
O2 La1 O2 77.95(16) 2_655 . ?
O2 La1 O2 77.95(16) 2_655 3_665 ?
O2 La1 O2 77.95(16) . 3_665 ?
O3 La1 C1 99.91(14) 2_655 2_655 ?
O3 La1 C1 159.27(13) 3_665 . ?
O3 La1 C1 159.28(14) . 2_655 ?
O3 La1 C1 82.20(14) 3_665 2_655 ?
O3 La1 C1 82.20(14) . 3_665 ?
O3 La1 C1 159.28(13) 2_655 3_665 ?
O3 La1 C1 99.91(14) . . ?
O3 La1 C1 99.91(14) 3_665 3_665 ?
O3 La1 C1 82.20(14) 2_655 . ?
O3 La1 O1 74.68(13) 2_655 2_655 ?
O3 La1 O1 76.31(14) 2_655 . ?
O3 La1 O1 76.31(14) 3_665 2_655 ?
O3 La1 O1 144.75(13) . 2_655 ?
O3 La1 O1 74.68(13) . . ?
O3 La1 O1 76.31(14) . 3_665 ?
O3 La1 O1 144.75(13) 2_655 3_665 ?
O3 La1 O1 74.68(13) 3_665 3_665 ?
O3 La1 O1 144.75(13) 3_665 . ?
O3 La1 O2 150.65(14) 2_655 . ?
O3 La1 O2 89.01(16) . . ?
O3 La1 O2 150.65(14) . 3_665 ?
O3 La1 O2 89.01(16) 3_665 3_665 ?
O3 La1 O2 89.01(16) 2_655 2_655 ?
O3 La1 O2 125.24(13) . 2_655 ?
O3 La1 O2 125.24(13) 2_655 3_665 ?
O3 La1 O2 150.65(14) 3_665 2_655 ?
O3 La1 O2 125.24(13) 3_665 . ?
O3 La1 O3 77.13(16) 2_655 3_665 ?
O3 La1 O3 77.13(16) 3_665 . ?
O3 La1 O3 77.13(16) 2_655 . ?

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
C1 C2 C3 C4 179.7(5) . . . . ?
C1 C2 C7 C6 178.6(4) . . . . ?
C1 C2 C7 N2 2.4(7) . . . . ?
C2 C1 O1 La1 -180.0(4) . . . . ?
C2 C3 C4 C5 2.0(9) . . . . ?
C2 C7 N2 C8 42.5(7) . . . . ?
C2 C7 N2 N1 -143.7(4) . . . . ?
C3 C2 C7 C6 0.1(7) . . . . ?
C3 C2 C7 N2 -176.2(4) . . . . ?
C3 C4 C5 C6 -0.7(9) . . . . ?
C4 C5 C6 C7 -0.8(8) . . . . ?
C5 C6 C7 C2 1.1(7) . . . . ?
C5 C6 C7 N2 177.5(4) . . . . ?
C6 C7 N2 C8 -133.8(5) . . . . ?
C6 C7 N2 N1 40.0(6) . . . . ?
C7 C2 C3 C4 -1.6(8) . . . . ?
C8 C9 C10 C11 177.3(4) . . . . ?
C8 C9 C10 N1 -1.7(5) . . . . ?
C9 C8 N2 C7 174.2(4) . . . . ?
C9 C8 N2 N1 0.0(5) . . . . ?
C9 C10 C11 C12 171.8(4) . . . 3 ?
C9 C10 C11 C12 -7.3(7) . . . . ?
C9 C10 N1 N2 1.6(5) . . . . ?
C10 C11 C12 C11 178.1(3) . . . 2 ?
C10 N1 N2 C7 -175.8(4) . . . . ?
C10 N1 N2 C8 -1.1(5) . . . . ?
C11 C10 N1 N2 -177.4(4) . . . . ?
C12 C11 C12 C11 -1.0(8) 3 . . 2 ?
N3A C13A O3 La1 160.3(5) . . . . ?
C14A N3A C13A O3 179.5(4) . . . . ?
C15A N3A C13A O3 1.0(7) . . . . ?
N3B C13B O3 La1 -159.8(5) . . . . ?
C14B N3B C13B O3 -179.9(4) . . . . ?
C15B N3B C13B O3 0.5(8) . . . . ?
N1 C10 C11 C12 -9.3(6) . . . 3 ?
N1 C10 C11 C12 171.6(4) . . . . ?
N2 C8 C9 C10 0.9(5) . . . . ?
O1 C1 C2 C3 -121.7(5) . . . . ?
O1 C1 C2 C7 59.8(6) . . . . ?
O2 C1 C2 C3 57.1(6) 2_655 . . . ?
O2 C1 C2 C7 -121.4(5) 2_655 . . . ?
O2 C1 O1 La1 1.3(5) 2_655 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_CP3
_database_code_depnum_ccdc_archive 'CCDC 1975158'
loop_
_audit_author_name
_audit_author_address
'shuangyan wu'
;Shenyang University of Chemical Technology
China
;
_audit_update_record             
;
2020-01-02 deposited with the CCDC.	2020-02-24 downloaded from the CCDC.
;
_audit_creation_date             2019-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '1(C45 H42 N9 O9 Pr1)'
_chemical_formula_sum            'C45 H42 N9 O9 Pr'
_chemical_formula_weight         993.79
_chemical_melting_point          ?
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'
Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   14.6570(6)
_cell_length_b                   14.6570(6)
_cell_length_c                   41.860(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     7787.9(8)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    3484
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.51
_shelx_estimated_absorpt_T_max   0.841
_shelx_estimated_absorpt_T_min   0.811
_exptl_absorpt_coefficient_mu    0.995
_exptl_absorpt_correction_T_max  0.837
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             3036
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            10471
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.007
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_min         1.676
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2647
_reflns_number_total             3052
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3052
_refine_ls_number_restraints     123
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0739P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1107
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed U13: Pr1(0)
 Fixed U23: Pr1(0)
 Fixed Uiso: H3(0.081) H4(0.097) H5(0.09) H6(0.073) H8(0.06) H9(0.063)
 H12(0.056) H13A(0.098) H14A(0.238) H14B(0.238) H14C(0.238) H15A(0.182)
 H15B(0.182) H15C(0.182) H13B(0.14) H14D(0.208) H14E(0.208) H14F(0.208)
 H15D(0.304) H15E(0.304) H15F(0.304)
 Fixed X: H3(0.340907) H4(0.183315) H5(0.114137) H6(0.201261) H8(0.531783)
 H9(0.553166) H12(0.509165) H13A(0.650962) H14A(0.470398) H14B(0.419235)
 H14C(0.400597) H15A(0.62709) H15B(0.528112) H15C(0.629572) H13B(0.44832)
 H14D(0.473536) H14E(0.574289) H14F(0.485016) H15D(0.374006) H15E(0.306073)
 H15F(0.316412) Pr1(0.666667)
 Fixed Y: H3(0.296443) H4(0.233328) H5(0.075517) H6(-0.019473) H8(0.127841)
 H9(-0.027967) H12(-0.203025) H13A(0.496561) H14A(0.289194) H14B(0.356508)
 H14C(0.30878) H15A(0.59202) H15B(0.534513) H15C(0.528108) H13B(0.221664)
 H14D(0.398547) H14E(0.433526) H14F(0.45452) H15D(0.195042) H15E(0.241903)
 H15F(0.156442) Pr1(0.333333)
 Fixed Z: H3(0.09651) H4(0.122913) H5(0.150437) H6(0.149737) H8(0.130934)
 H9(0.134872) H12(0.126095) H13A(0.004652) H14A(-0.046652) H14B(-0.056843)
 H14C(-0.02235) H15A(-0.034569) H15B(-0.056792) H15C(-0.06426) H13B(0.010735)
 H14D(-0.062809) H14E(-0.041831) H14F(-0.02993) H15D(-0.05981) H15E(-0.046498)
 H15F(-0.026859)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4679(3) 0.2246(3) 0.08759(10) 0.0472(9) Uani 1 1 d . . . . .
C2 C 0.3658(3) 0.1761(3) 0.10626(11) 0.0494(10) Uani 1 1 d . . . . .
C3 C 0.3123(4) 0.2321(3) 0.10708(13) 0.0672(13) Uani 1 1 d . . . . .
H3 H 0.340907 0.296443 0.096510 0.081 Uiso 1 1 calc R . . . .
C4 C 0.2184(4) 0.1952(4) 0.12304(15) 0.0804(16) Uani 1 1 d . . . . .
H4 H 0.183315 0.233328 0.122913 0.097 Uiso 1 1 calc R . . . .
C5 C 0.1771(4) 0.1010(4) 0.13925(14) 0.0750(15) Uani 1 1 d . . . . .
H5 H 0.114137 0.075517 0.150437 0.090 Uiso 1 1 calc R . . . .
C6 C 0.2294(3) 0.0442(3) 0.13884(11) 0.0607(12) Uani 1 1 d . . . . .
H6 H 0.201261 -0.019473 0.149737 0.073 Uiso 1 1 calc R . . . .
C7 C 0.3224(3) 0.0813(3) 0.12249(10) 0.0469(9) Uani 1 1 d . . . . .
C8 C 0.4788(3) 0.0578(3) 0.12926(10) 0.0498(9) Uani 1 1 d . . . . .
H8 H 0.531783 0.127841 0.130934 0.060 Uiso 1 1 calc R . . . .
C9 C 0.4907(3) -0.0276(3) 0.13140(11) 0.0528(10) Uani 1 1 d . . . . .
H9 H 0.553166 -0.027967 0.134872 0.063 Uiso 1 1 calc R . . . .
C10 C 0.3900(3) -0.1155(3) 0.12735(9) 0.0437(9) Uani 1 1 d . . . . .
C11 C 0.3602(3) -0.2270(3) 0.12629(9) 0.0431(8) Uani 1 1 d . . . . .
C12 C 0.4386(3) -0.2555(3) 0.12621(9) 0.0466(9) Uani 1 1 d . . . . .
H12 H 0.509165 -0.203025 0.126095 0.056 Uiso 1 1 calc R . . . .
N3A N 0.5462(6) 0.4367(6) -0.02792(15) 0.096(2) Uani 0.730(6) 1 d D U . A 1
C13A C 0.5914(5) 0.4345(6) -0.00161(14) 0.0817(19) Uani 0.730(6) 1 d D U . A 1
H13A H 0.650962 0.496561 0.004652 0.098 Uiso 0.730(6) 1 calc R . . A 1
C14A C 0.4505(8) 0.3390(9) -0.0395(3) 0.159(4) Uani 0.730(6) 1 d D U . A 1
H14A H 0.470398 0.289194 -0.046652 0.238 Uiso 0.730(6) 1 calc GR . . A 1
H14B H 0.419235 0.356508 -0.056843 0.238 Uiso 0.730(6) 1 calc GR . . A 1
H14C H 0.400597 0.308780 -0.022350 0.238 Uiso 0.730(6) 1 calc GR . . A 1
C15A C 0.5861(8) 0.5308(8) -0.04755(19) 0.121(3) Uani 0.730(6) 1 d D U . A 1
H15A H 0.627090 0.592020 -0.034569 0.182 Uiso 0.730(6) 1 calc GR . . A 1
H15B H 0.528112 0.534513 -0.056792 0.182 Uiso 0.730(6) 1 calc GR . . A 1
H15C H 0.629572 0.528108 -0.064260 0.182 Uiso 0.730(6) 1 calc GR . . A 1
N3B N 0.4453(14) 0.299(2) -0.0246(4) 0.140(5) Uani 0.270(6) 1 d D U . A 2
C13B C 0.4833(10) 0.2883(15) 0.0015(3) 0.116(4) Uani 0.270(6) 1 d D U . A 2
H13B H 0.448320 0.221664 0.010735 0.140 Uiso 0.270(6) 1 calc R . . A 2
C14B C 0.500(2) 0.4065(19) -0.0414(5) 0.139(7) Uani 0.270(6) 1 d D U . A 2
H14D H 0.473536 0.398547 -0.062809 0.208 Uiso 0.270(6) 1 calc GR . . A 2
H14E H 0.574289 0.433526 -0.041831 0.208 Uiso 0.270(6) 1 calc GR . . A 2
H14F H 0.485016 0.454520 -0.029930 0.208 Uiso 0.270(6) 1 calc GR . . A 2
C15B C 0.3525(15) 0.216(2) -0.0408(5) 0.202(10) Uani 0.270(6) 1 d D U . A 2
H15D H 0.374006 0.195042 -0.059810 0.304 Uiso 0.270(6) 1 calc GR . . A 2
H15E H 0.306073 0.241903 -0.046498 0.304 Uiso 0.270(6) 1 calc GR . . A 2
H15F H 0.316412 0.156442 -0.026859 0.304 Uiso 0.270(6) 1 calc GR . . A 2
Pr1 Pr 0.666667 0.333333 0.05650(2) 0.03739(16) Uani 1 3 d DS T P A .
N1 N 0.3744(2) 0.0217(2) 0.12418(8) 0.0470(8) Uani 1 1 d . . . . .
N2 N 0.3187(2) -0.0859(2) 0.12323(8) 0.0476(8) Uani 1 1 d . . . . .
O1 O 0.5380(2) 0.3150(2) 0.09600(8) 0.0725(10) Uani 1 1 d . . . . .
O2 O 0.4806(2) 0.1780(2) 0.06511(7) 0.0624(8) Uani 1 1 d . . . . .
O3 O 0.5618(3) 0.3562(3) 0.01606(8) 0.0796(10) Uani 1 1 d D 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
C1 C2 1.513(5) . ?
C1 O1 1.255(5) . ?
C1 O2 1.231(5) . ?
C2 C3 1.390(6) . ?
C2 C7 1.384(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.374(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.371(6) . ?
C7 N1 1.420(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.349(6) . ?
C8 N1 1.363(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.402(5) . ?
C10 C11 1.467(5) . ?
C10 N2 1.329(5) . ?
C11 C12 1.385(5) 2_545 ?
C11 C12 1.405(5) . ?
C12 H12 0.9300 . ?
N3A C13A 1.294(9) . ?
N3A C14A 1.498(12) . ?
N3A C15A 1.454(11) . ?
C13A H13A 0.9300 . ?
C13A O3 1.247(7) . ?
C14A H14A 0.9600 . ?
C14A H14B 0.9600 . ?
C14A H14C 0.9600 . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
N3B C13B 1.27(2) . ?
N3B C14B 1.53(3) . ?
N3B C15B 1.46(2) . ?
C13B H13B 0.9300 . ?
C13B O3 1.241(12) . ?
C14B H14D 0.9600 . ?
C14B H14E 0.9600 . ?
C14B H14F 0.9600 . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 0.9600 . ?
Pr1 O1 2.419(3) 2_655 ?
Pr1 O1 2.419(3) 3_665 ?
Pr1 O1 2.419(3) . ?
Pr1 O2 2.558(3) 3_665 ?
Pr1 O2 2.557(3) . ?
Pr1 O2 2.557(3) 2_655 ?
Pr1 O3 2.420(3) 3_665 ?
Pr1 O3 2.420(3) 2_655 ?
Pr1 O3 2.420(3) . ?
N1 N2 1.366(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 116.5(4) . . ?
O2 C1 C2 121.6(4) . . ?
O2 C1 O1 121.9(4) . . ?
C3 C2 C1 116.9(4) . . ?
C7 C2 C1 125.1(3) . . ?
C7 C2 C3 118.0(4) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 121.9(4) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.1(4) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(4) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.5(4) . . ?
C7 C6 H6 119.7 . . ?
C2 C7 N1 121.6(3) . . ?
C6 C7 C2 120.7(4) . . ?
C6 C7 N1 117.7(4) . . ?
C9 C8 H8 126.5 . . ?
C9 C8 N1 106.9(3) . . ?
N1 C8 H8 126.5 . . ?
C8 C9 H9 126.9 . . ?
C8 C9 C10 106.3(3) . . ?
C10 C9 H9 126.9 . . ?
C9 C10 C11 128.2(3) . . ?
N2 C10 C9 110.7(3) . . ?
N2 C10 C11 121.0(3) . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 C10 121.3(3) 2_545 . ?
C12 C11 C12 118.8(4) 2_545 . ?
C11 C12 C11 121.2(4) 3_655 . ?
C11 C12 H12 119.4 3_655 . ?
C11 C12 H12 119.4 . . ?
C13A N3A C14A 119.8(7) . . ?
C13A N3A C15A 122.5(8) . . ?
C15A N3A C14A 117.7(7) . . ?
N3A C13A H13A 117.2 . . ?
O3 C13A N3A 125.6(7) . . ?
O3 C13A H13A 117.2 . . ?
N3A C14A H14A 109.5 . . ?
N3A C14A H14B 109.5 . . ?
N3A C14A H14C 109.5 . . ?
H14A C14A H14B 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
N3A C15A H15A 109.5 . . ?
N3A C15A H15B 109.5 . . ?
N3A C15A H15C 109.5 . . ?
H15A C15A H15B 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C13B N3B C14B 119.1(17) . . ?
C13B N3B C15B 125(2) . . ?
C15B N3B C14B 115.5(14) . . ?
N3B C13B H13B 116.2 . . ?
O3 C13B N3B 128(2) . . ?
O3 C13B H13B 116.2 . . ?
N3B C14B H14D 109.5 . . ?
N3B C14B H14E 109.5 . . ?
N3B C14B H14F 109.5 . . ?
H14D C14B H14E 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
N3B C15B H15D 109.5 . . ?
N3B C15B H15E 109.5 . . ?
N3B C15B H15F 109.5 . . ?
H15D C15B H15E 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
O1 Pr1 O1 78.43(14) 2_655 . ?
O1 Pr1 O1 78.43(14) 3_665 . ?
O1 Pr1 O1 78.43(14) 2_655 3_665 ?
O1 Pr1 O2 126.66(11) 3_665 . ?
O1 Pr1 O2 126.66(11) . 2_655 ?
O1 Pr1 O2 126.66(11) 2_655 3_665 ?
O1 Pr1 O2 74.56(10) . 3_665 ?
O1 Pr1 O2 74.56(10) 2_655 . ?
O1 Pr1 O2 51.70(9) . . ?
O1 Pr1 O2 74.56(10) 3_665 2_655 ?
O1 Pr1 O2 51.70(9) 3_665 3_665 ?
O1 Pr1 O2 51.70(9) 2_655 2_655 ?
O1 Pr1 O3 88.83(13) . . ?
O1 Pr1 O3 149.42(12) 3_665 2_655 ?
O1 Pr1 O3 88.83(13) 3_665 3_665 ?
O1 Pr1 O3 126.41(11) 2_655 3_665 ?
O1 Pr1 O3 126.41(11) . 2_655 ?
O1 Pr1 O3 88.83(13) 2_655 2_655 ?
O1 Pr1 O3 126.41(11) 3_665 . ?
O1 Pr1 O3 149.42(12) . 3_665 ?
O1 Pr1 O3 149.42(12) 2_655 . ?
O2 Pr1 O2 118.05(3) 2_655 3_665 ?
O2 Pr1 O2 118.05(3) . 3_665 ?
O2 Pr1 O2 118.05(3) 2_655 . ?
O3 Pr1 O2 143.71(11) 3_665 . ?
O3 Pr1 O2 75.73(11) 3_665 3_665 ?
O3 Pr1 O2 75.73(11) 2_655 2_655 ?
O3 Pr1 O2 143.71(11) . 2_655 ?
O3 Pr1 O2 74.71(11) 2_655 . ?
O3 Pr1 O2 143.71(11) 2_655 3_665 ?
O3 Pr1 O2 75.73(11) . . ?
O3 Pr1 O2 74.71(11) 3_665 2_655 ?
O3 Pr1 O2 74.71(11) . 3_665 ?
O3 Pr1 O3 76.47(13) 3_665 . ?
O3 Pr1 O3 76.47(13) 2_655 3_665 ?
O3 Pr1 O3 76.47(13) 2_655 . ?
C8 N1 C7 127.9(3) . . ?
C8 N1 N2 111.1(3) . . ?
N2 N1 C7 120.8(3) . . ?
C10 N2 N1 105.0(3) . . ?
C1 O1 Pr1 96.1(2) . . ?
C1 O2 Pr1 90.2(2) . . ?
C13A O3 Pr1 126.1(4) . . ?
C13B O3 Pr1 129.1(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 179.4(5) . . . . ?
C1 C2 C7 C6 179.8(4) . . . . ?
C1 C2 C7 N1 3.0(6) . . . . ?
C2 C1 O1 Pr1 -180.0(3) . . . . ?
C2 C1 O2 Pr1 179.9(3) . . . . ?
C2 C3 C4 C5 1.3(9) . . . . ?
C2 C7 N1 C8 42.3(6) . . . . ?
C2 C7 N1 N2 -143.2(4) . . . . ?
C3 C2 C7 C6 -0.1(6) . . . . ?
C3 C2 C7 N1 -176.9(4) . . . . ?
C3 C4 C5 C6 -1.0(9) . . . . ?
C4 C5 C6 C7 0.2(8) . . . . ?
C5 C6 C7 C2 0.3(7) . . . . ?
C5 C6 C7 N1 177.3(4) . . . . ?
C6 C7 N1 C8 -134.6(4) . . . . ?
C6 C7 N1 N2 39.9(5) . . . . ?
C7 C2 C3 C4 -0.8(8) . . . . ?
C7 N1 N2 C10 -176.2(3) . . . . ?
C8 C9 C10 C11 177.2(4) . . . . ?
C8 C9 C10 N2 -0.7(5) . . . . ?
C8 N1 N2 C10 -0.8(4) . . . . ?
C9 C8 N1 C7 175.4(4) . . . . ?
C9 C8 N1 N2 0.4(5) . . . . ?
C9 C10 C11 C12 -6.7(6) . . . . ?
C9 C10 C11 C12 171.6(4) . . . 2_545 ?
C9 C10 N2 N1 0.9(4) . . . . ?
C10 C11 C12 C11 177.8(3) . . . 3_655 ?
C11 C10 N2 N1 -177.2(3) . . . . ?
C12 C11 C12 C11 -0.5(8) 2_545 . . 3_655 ?
N3A C13A O3 Pr1 161.9(4) . . . . ?
C14A N3A C13A O3 -0.6(6) . . . . ?
C15A N3A C13A O3 -179.1(4) . . . . ?
N3B C13B O3 Pr1 -161.1(5) . . . . ?
C14B N3B C13B O3 0.6(8) . . . . ?
C15B N3B C13B O3 179.8(4) . . . . ?
N1 C8 C9 C10 0.1(5) . . . . ?
N2 C10 C11 C12 -10.6(6) . . . 2_545 ?
N2 C10 C11 C12 171.1(4) . . . . ?
O1 C1 C2 C3 57.7(6) . . . . ?
O1 C1 C2 C7 -122.1(5) . . . . ?
O1 C1 O2 Pr1 0.7(4) . . . . ?
O2 C1 C2 C3 -121.5(5) . . . . ?
O2 C1 C2 C7 58.7(6) . . . . ?
O2 C1 O1 Pr1 -0.7(5) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.000 382.3 28.0 ?
2 0.000 0.000 0.390 13.3 0.0 ?
3 0.000 0.000 0.610 13.3 0.4 ?
4 0.333 0.667 0.667 382.3 28.0 ?
5 -0.333 0.333 0.333 382.3 28.0 ?
6 0.333 0.667 0.277 13.3 0.4 ?
7 0.333 0.667 0.057 13.3 0.0 ?
8 0.667 0.333 0.943 13.3 0.4 ?
9 0.667 0.333 0.723 13.3 0.0 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_CP2
_database_code_depnum_ccdc_archive 'CCDC 1975218'
loop_
_audit_author_name
_audit_author_address
'shuangyan wu'
;Shenyang University of Chemical Technology
China
;
_audit_update_record             
;
2020-01-03 deposited with the CCDC.	2020-02-24 downloaded from the CCDC.
;
_audit_creation_date             2020-01-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '1(C45 H42 Ce1 N9 O9)'
_chemical_formula_sum            'C45 H42 Ce N9 O9'
_chemical_formula_weight         993.00
_chemical_melting_point          ?
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'
Ce Ce -0.2486 2.6331 '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'

_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.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   14.6306(5)
_cell_length_b                   14.6306(5)
_cell_length_c                   41.757(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     7740.8(6)
_cell_formula_units_Z            5.99994
_cell_measurement_reflns_used    5048
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.01
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   0.849
_shelx_estimated_absorpt_T_min   0.820
_exptl_absorpt_coefficient_mu    0.939
_exptl_absorpt_correction_T_max  0.7832
_exptl_absorpt_correction_T_min  0.7442
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             3030
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            17009
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.081
_diffrn_reflns_theta_max         25.081
_diffrn_reflns_theta_min         1.463
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2768
_reflns_number_total             3066
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3066
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0360
_refine_ls_restrained_S_all      1.138
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0670P)²+9.5751P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1108
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 O3, C13
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 O1, Ce1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 Ce1, O2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
Uanis(N1) \\sim Ueq, Uanis(C15) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C12(H12), C13(H13)
4.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4689(3) 0.2253(3) 0.08771(10) 0.0520(9) Uani 1 1 d . . . . .
C2 C 0.3669(3) 0.1768(3) 0.10608(11) 0.0535(10) Uani 1 1 d . . . . .
C3 C 0.3148(4) 0.2340(4) 0.10682(14) 0.0706(13) Uani 1 1 d . . . . .
H3 H 0.343648 0.298505 0.096282 0.085 Uiso 1 1 calc R . . . .
C4 C 0.2201(4) 0.1960(4) 0.12308(15) 0.0829(16) Uani 1 1 d . . . . .
H4 H 0.185666 0.234996 0.123351 0.099 Uiso 1 1 calc R . . . .
C5 C 0.1774(4) 0.1021(4) 0.13861(15) 0.0799(15) Uani 1 1 d . . . . .
H5 H 0.113388 0.076336 0.149264 0.096 Uiso 1 1 calc R . . . .
C6 C 0.2285(3) 0.0448(3) 0.13865(12) 0.0653(12) Uani 1 1 d . . . . .
H6 H 0.199627 -0.019020 0.149603 0.078 Uiso 1 1 calc R . . . .
C7 C 0.3229(3) 0.0821(3) 0.12240(10) 0.0506(9) Uani 1 1 d . . . . .
C8 C 0.4795(3) 0.0583(3) 0.12940(10) 0.0549(10) Uani 1 1 d . . . . .
H8 H 0.532403 0.128519 0.131160 0.066 Uiso 1 1 calc R . . . .
C9 C 0.4914(3) -0.0281(3) 0.13187(11) 0.0549(10) Uani 1 1 d . . . . .
H9 H 0.553635 -0.028998 0.135632 0.066 Uiso 1 1 calc R . . . .
C10 C 0.3903(3) -0.1151(3) 0.12752(9) 0.0481(9) Uani 1 1 d . . . . .
C11 C 0.3607(3) -0.2269(3) 0.12618(9) 0.0464(8) Uani 1 1 d . . . . .
C12 C 0.4385(3) -0.2554(3) 0.12603(9) 0.0500(9) Uani 1 1 d . . . . .
H12 H 0.509168 -0.202890 0.125828 0.060 Uiso 1 1 calc R . . . .
C13 C 0.5652(6) 0.1543(5) -0.00054(15) 0.108(2) Uani 1 1 d . U . . .
H13 H 0.501185 0.146405 0.006367 0.130 Uiso 1 1 calc R . . . .
C14 C 0.4725(8) 0.0543(7) -0.0464(2) 0.184(5) Uani 1 1 d . . . . .
H14A H 0.412632 0.029185 -0.032458 0.277 Uiso 1 1 calc GR . . . .
H14B H 0.471227 -0.004574 -0.057059 0.277 Uiso 1 1 calc GR . . . .
H14C H 0.470057 0.101024 -0.062081 0.277 Uiso 1 1 calc GR . . . .
C15 C 0.6683(10) 0.1190(10) -0.0375(3) 0.215(6) Uani 1 1 d . U . . .
H15A H 0.691905 0.157475 -0.057194 0.322 Uiso 1 1 calc GR . . . .
H15B H 0.659518 0.049907 -0.040227 0.322 Uiso 1 1 calc GR . . . .
H15C H 0.719642 0.155877 -0.021010 0.322 Uiso 1 1 calc GR . . . .
N1 N 0.5671(6) 0.1093(5) -0.02816(14) 0.121(2) Uani 1 1 d . U . . .
N2 N 0.3756(2) 0.0223(2) 0.12390(8) 0.0508(8) Uani 1 1 d . . . . .
N3 N 0.3192(3) -0.0851(2) 0.12290(9) 0.0516(8) Uani 1 1 d . . . . .
O1 O 0.5389(2) 0.3157(2) 0.09553(9) 0.0735(9) Uani 1 1 d . U . . .
O2 O 0.4812(2) 0.1770(2) 0.06475(8) 0.0652(8) Uani 1 1 d . U . . .
O3 O 0.6447(3) 0.2063(3) 0.01645(8) 0.0803(10) Uani 1 1 d . U . . .
Ce1 Ce 0.666667 0.333333 0.05647(2) 0.03613(15) Uani 1 3 d S TU P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.503(6) . ?
C1 O1 1.245(5) . ?
C1 O2 1.256(5) . ?
C1 Ce1 2.828(4) . ?
C2 C3 1.386(6) . ?
C2 C7 1.380(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.357(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.373(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.383(6) . ?
C7 N2 1.428(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.364(6) . ?
C8 N2 1.356(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.400(5) . ?
C10 C11 1.468(5) . ?
C10 N3 1.330(5) . ?
C11 C12 1.394(5) . ?
C11 C12 1.391(5) 2_545 ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 N1 1.335(8) . ?
C13 O3 1.246(7) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14 N1 1.425(10) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C15 N1 1.468(12) . ?
N2 N3 1.362(4) . ?
O1 Ce1 2.395(3) . ?
O2 Ce1 2.551(3) . ?
O3 Ce1 2.399(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Ce1 174.8(3) . . ?
O1 C1 C2 117.6(4) . . ?
O1 C1 O2 121.6(4) . . ?
O1 C1 Ce1 57.2(2) . . ?
O2 C1 C2 120.8(4) . . ?
O2 C1 Ce1 64.4(2) . . ?
C3 C2 C1 116.2(4) . . ?
C7 C2 C1 125.5(4) . . ?
C7 C2 C3 118.2(4) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(5) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.3(5) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 119.9(4) . . ?
C7 C6 H6 120.0 . . ?
C2 C7 C6 120.7(4) . . ?
C2 C7 N2 120.8(4) . . ?
C6 C7 N2 118.4(4) . . ?
C9 C8 H8 126.6 . . ?
N2 C8 H8 126.6 . . ?
N2 C8 C9 106.9(4) . . ?
C8 C9 H9 127.3 . . ?
C8 C9 C10 105.4(4) . . ?
C10 C9 H9 127.3 . . ?
C9 C10 C11 127.3(3) . . ?
N3 C10 C9 111.4(3) . . ?
N3 C10 C11 121.2(3) . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 C10 121.0(3) 2_545 . ?
C12 C11 C12 118.7(4) 2_545 . ?
C11 C12 C11 121.3(4) 3_655 . ?
C11 C12 H12 119.4 3_655 . ?
C11 C12 H12 119.4 . . ?
N1 C13 H13 118.3 . . ?
O3 C13 H13 118.3 . . ?
O3 C13 N1 123.3(7) . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
C13 N1 C14 119.2(8) . . ?
C13 N1 C15 116.7(7) . . ?
C14 N1 C15 124.1(8) . . ?
C8 N2 C7 127.8(3) . . ?
C8 N2 N3 111.7(3) . . ?
N3 N2 C7 120.3(3) . . ?
C10 N3 N2 104.7(3) . . ?
C1 O1 Ce1 96.9(3) . . ?
C1 O2 Ce1 89.2(2) . . ?
C13 O3 Ce1 126.3(4) . . ?
C1 Ce1 C1 100.43(11) 2_655 . ?
C1 Ce1 C1 100.43(11) 3_665 . ?
C1 Ce1 C1 100.43(11) 2_655 3_665 ?
O1 Ce1 C1 102.89(13) . 2_655 ?
O1 Ce1 C1 25.91(11) 3_665 3_665 ?
O1 Ce1 C1 74.60(11) 3_665 2_655 ?
O1 Ce1 C1 25.91(11) . . ?
O1 Ce1 C1 102.89(13) 2_655 3_665 ?
O1 Ce1 C1 74.60(11) . 3_665 ?
O1 Ce1 C1 25.91(11) 2_655 2_655 ?
O1 Ce1 C1 74.61(11) 2_655 . ?
O1 Ce1 C1 102.89(13) 3_665 . ?
O1 Ce1 O1 78.74(14) 2_655 . ?
O1 Ce1 O1 78.74(14) 2_655 3_665 ?
O1 Ce1 O1 78.74(14) 3_665 . ?
O1 Ce1 O2 52.27(10) 2_655 2_655 ?
O1 Ce1 O2 52.27(10) . . ?
O1 Ce1 O2 74.27(11) 2_655 . ?
O1 Ce1 O2 127.32(12) 3_665 . ?
O1 Ce1 O2 127.32(12) . 2_655 ?
O1 Ce1 O2 127.32(12) 2_655 3_665 ?
O1 Ce1 O2 74.27(11) . 3_665 ?
O1 Ce1 O2 74.27(11) 3_665 2_655 ?
O1 Ce1 O2 52.27(10) 3_665 3_665 ?
O1 Ce1 O3 88.32(14) 2_655 . ?
O1 Ce1 O3 148.90(13) . 2_655 ?
O1 Ce1 O3 126.57(12) 3_665 3_665 ?
O1 Ce1 O3 88.32(14) 3_665 2_655 ?
O1 Ce1 O3 88.32(14) . 3_665 ?
O1 Ce1 O3 148.89(13) 2_655 3_665 ?
O1 Ce1 O3 126.57(12) 2_655 2_655 ?
O1 Ce1 O3 148.89(13) 3_665 . ?
O1 Ce1 O3 126.57(12) . . ?
O2 Ce1 C1 96.44(11) 2_655 3_665 ?
O2 Ce1 C1 26.36(10) 3_665 3_665 ?
O2 Ce1 C1 26.36(10) 2_655 2_655 ?
O2 Ce1 C1 126.61(11) 2_655 . ?
O2 Ce1 C1 26.36(10) . . ?
O2 Ce1 C1 126.61(11) . 3_665 ?
O2 Ce1 C1 96.44(11) . 2_655 ?
O2 Ce1 C1 126.61(11) 3_665 2_655 ?
O2 Ce1 C1 96.44(11) 3_665 . ?
O2 Ce1 O2 118.19(3) . 3_665 ?
O2 Ce1 O2 118.19(3) 2_655 . ?
O2 Ce1 O2 118.19(3) 2_655 3_665 ?
O3 Ce1 C1 81.42(13) 3_665 . ?
O3 Ce1 C1 100.67(12) . . ?
O3 Ce1 C1 100.67(12) 3_665 3_665 ?
O3 Ce1 C1 158.10(13) 3_665 2_655 ?
O3 Ce1 C1 81.41(13) . 2_655 ?
O3 Ce1 C1 158.10(13) . 3_665 ?
O3 Ce1 C1 81.41(13) 2_655 3_665 ?
O3 Ce1 C1 158.11(13) 2_655 . ?
O3 Ce1 C1 100.67(12) 2_655 2_655 ?
O3 Ce1 O2 143.63(12) 2_655 . ?
O3 Ce1 O2 74.31(11) . . ?
O3 Ce1 O2 74.31(11) 2_655 2_655 ?
O3 Ce1 O2 74.31(11) 3_665 3_665 ?
O3 Ce1 O2 75.44(12) 2_655 3_665 ?
O3 Ce1 O2 143.63(12) . 3_665 ?
O3 Ce1 O2 143.63(12) 3_665 2_655 ?
O3 Ce1 O2 75.44(12) 3_665 . ?
O3 Ce1 O2 75.44(12) . 2_655 ?
O3 Ce1 O3 76.83(14) 2_655 3_665 ?
O3 Ce1 O3 76.83(14) . 3_665 ?
O3 Ce1 O3 76.83(14) . 2_655 ?

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
C1 C2 C3 C4 179.9(5) . . . . ?
C1 C2 C7 C6 179.8(4) . . . . ?
C1 C2 C7 N2 2.1(7) . . . . ?
C2 C1 O1 Ce1 -179.6(3) . . . . ?
C2 C1 O2 Ce1 179.5(4) . . . . ?
C2 C3 C4 C5 0.2(9) . . . . ?
C2 C7 N2 C8 43.7(6) . . . . ?
C2 C7 N2 N3 -143.2(4) . . . . ?
C3 C2 C7 C6 0.9(7) . . . . ?
C3 C2 C7 N2 -176.8(4) . . . . ?
C3 C4 C5 C6 0.9(10) . . . . ?
C4 C5 C6 C7 -1.0(9) . . . . ?
C5 C6 C7 C2 0.1(7) . . . . ?
C5 C6 C7 N2 177.9(5) . . . . ?
C6 C7 N2 C8 -134.0(5) . . . . ?
C6 C7 N2 N3 39.1(6) . . . . ?
C7 C2 C3 C4 -1.1(8) . . . . ?
C7 N2 N3 C10 -174.8(4) . . . . ?
C8 C9 C10 C11 176.3(4) . . . . ?
C8 C9 C10 N3 -0.5(5) . . . . ?
C8 N2 N3 C10 -0.7(5) . . . . ?
C9 C8 N2 C7 174.0(4) . . . . ?
C9 C8 N2 N3 0.4(5) . . . . ?
C9 C10 C11 C12 171.3(4) . . . 2_545 ?
C9 C10 C11 C12 -6.7(6) . . . . ?
C9 C10 N3 N2 0.7(5) . . . . ?
C10 C11 C12 C11 177.2(3) . . . 3_655 ?
C11 C10 N3 N2 -176.3(3) . . . . ?
C12 C11 C12 C11 -0.9(8) 2_545 . . 3_655 ?
N1 C13 O3 Ce1 159.5(5) . . . . ?
N2 C8 C9 C10 0.1(5) . . . . ?
N3 C10 C11 C12 -12.2(6) . . . 2_545 ?
N3 C10 C11 C12 169.8(4) . . . . ?
O1 C1 C2 C3 56.2(6) . . . . ?
O1 C1 C2 C7 -122.8(5) . . . . ?
O1 C1 O2 Ce1 1.5(4) . . . . ?
O2 C1 C2 C3 -121.9(5) . . . . ?
O2 C1 C2 C7 59.2(6) . . . . ?
O2 C1 O1 Ce1 -1.6(5) . . . . ?
O3 C13 N1 C14 -178.0(7) . . . . ?
O3 C13 N1 C15 3.0(12) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.000 569.9 30.8 ?
2 0.000 0.000 0.390 15.4 0.5 ?
3 0.000 0.000 0.610 15.4 0.8 ?
4 0.333 0.667 0.667 569.9 30.8 ?
5 -0.333 0.333 0.333 569.9 30.8 ?
6 0.333 0.667 0.277 15.4 0.8 ?
7 0.333 0.667 0.057 15.4 0.5 ?
8 0.667 0.333 0.943 15.4 0.8 ?
9 0.667 0.333 0.723 15.4 0.5 ?

_olex2_submission_special_instructions 'No special instructions were received'
