# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_Eu
_database_code_depnum_ccdc_archive 'CCDC 1550719'
_audit_update_record             
;
2017-05-17 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;
_audit_creation_date             2017-05-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6

#==============================================================================
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H25 Eu N9 O10, C19 H25 N6, 2(C2 H3 N)'
_chemical_formula_sum            'C42 H56 Eu N17 O10'
_chemical_formula_weight         1110.99
_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'
Eu Eu -0.1578 3.6682 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.7079(6)
_cell_length_b                   12.6310(6)
_cell_length_c                   18.8051(9)
_cell_angle_alpha                78.661(4)
_cell_angle_beta                 84.036(4)
_cell_angle_gamma                69.641(4)
_cell_volume                     2554.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    16795
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.59
_cell_measurement_theta_min      1.75
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.298
_exptl_absorpt_correction_T_max  0.9183
_exptl_absorpt_correction_T_min  0.3608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270.
Afterwards scaling of reflection intensities was performed within STOE LANA.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1140
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.069
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0950
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.819
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23567
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         1.746
_diffrn_ambient_temperature      100
_diffrn_detector                 'Dectris Pilatus 100k'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.819
_diffrn_measurement_device       '4-circle goniometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       ?
_diffrn_radiation_collimation    '0.5mm monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Mo LFF Sealed Tube'
_diffrn_source_type              'Xenocs Genix3D microfocus'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8623
_reflns_number_total             12205
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'X-Area Pilatus3_SV 1.31.127.0 (STOE, 2016)'
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
PLATON (A.L.Spek, 2009)
;
_computing_data_reduction        
;
X-Area Integrate 1.71.0.0 (STOE, 2016)
X-Area LANA 1.70.0.0 (STOE, 2017)
PLATON (A.L.Spek, 2009)
;
_computing_structure_solution    'SHELXS-2016/6 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_molecular_graphics    'Diamond 4, Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.77, Darmstadt 2016
MS Word (Microsoft)
Olex2 (Dolomanov et al., 2009)
;
_refine_diff_density_max         2.070
_refine_diff_density_min         -1.846
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     674
_refine_ls_number_reflns         12205
_refine_ls_number_restraints     39
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0484
_refine_ls_restrained_S_all      0.920
_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)+(0.0497P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1098
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups, All O(H,H) groups
2. Restrained distances
 C3-C13 \\sim C14B-C15B
 with sigma of 0.04
 C12B-C3 \\sim C12B-C13 \\sim C12B-C14B \\sim C12B-C15B
 with sigma of 0.02
 C3-C13 \\sim C14A-C15A
 with sigma of 0.04
 C12A-C3 \\sim C12A-C13 \\sim C12A-C14A \\sim C12A-C15A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C12B \\sim C14B \\sim C15B: within 2A with sigma of 0.004 and sigma for
terminal atoms of 0.008
C12A \\sim C14A \\sim C15A: within 2A with sigma of 0.004 and sigma for
terminal atoms of 0.008
4. Others
 Fixed Sof: C12A(0.5) C12B(0.5) H13A(0.5) H13B(0.5) H13C(0.5) H13D(0.5)
 H13E(0.5) H13F(0.5) C14A(0.5) H14A(0.5) H14B(0.5) H14C(0.5) C14B(0.5)
 H14D(0.5) H14E(0.5) H14F(0.5) C15A(0.5) H15A(0.5) H15B(0.5) H15C(0.5)
 C15B(0.5) H15D(0.5) H15E(0.5) H15F(0.5)
5.a Rotating group:
 O10(H10A,H10B)
5.b Me refined with riding coordinates:
 C13(H13A,H13B,H13C), C13(H13D,H13E,H13F)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C7(H7), C9(H9), C10(H10), N8(H8), N9(H9A), C21(H21), C23(H23),
  C26(H26), C28(H28), C29(H29)
5.d Idealised Me refined as rotating group:
 C14A(H14A,H14B,H14C), C14B(H14D,H14E,H14F), C15A(H15A,H15B,H15C), C15B(H15D,
 H15E,H15F), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C),
 C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C36(H36A,H36B,
 H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C40(H40A,H40B,H40C), C42(H42A,
 H42B,H42C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
Eu01 Eu 0.47141(2) 0.16587(2) 0.66588(2) 0.02728(7) Uani 1 1 d . . . . .
O1 O 0.6964(3) 0.1204(3) 0.63315(17) 0.0356(7) Uani 1 1 d . . . . .
O2 O 0.5897(3) 0.2953(3) 0.64285(17) 0.0366(7) Uani 1 1 d . . . . .
O3 O 0.7810(3) 0.2525(4) 0.6066(2) 0.0614(11) Uani 1 1 d . . . . .
O4 O 0.5108(3) 0.1976(3) 0.53085(16) 0.0324(7) Uani 1 1 d . . . . .
O5 O 0.3625(3) 0.1325(3) 0.56692(16) 0.0322(7) Uani 1 1 d . . . . .
O6 O 0.3941(3) 0.1866(3) 0.45108(16) 0.0388(8) Uani 1 1 d . . . . .
O7 O 0.3788(3) 0.0510(3) 0.76643(17) 0.0382(7) Uani 1 1 d . . . . .
O8 O 0.2473(3) 0.1906(3) 0.70291(17) 0.0367(7) Uani 1 1 d . . . . .
O9 O 0.1850(3) 0.0778(3) 0.78874(17) 0.0412(8) Uani 1 1 d . . . . .
O10 O 0.5635(3) -0.0329(2) 0.65153(16) 0.0326(7) Uani 1 1 d . . . . .
H10A H 0.644041 -0.053630 0.648685 0.049 Uiso 1 1 d GR . . . .
H10B H 0.539731 -0.044680 0.611424 0.049 Uiso 1 1 d GR . . . .
N1 N 0.3941(3) 0.3068(3) 0.75563(18) 0.0274(7) Uani 1 1 d . . . . .
N2 N 0.5857(3) 0.1178(3) 0.78315(19) 0.0316(8) Uani 1 1 d . . . . .
N3 N 0.3262(3) 0.3562(3) 0.61617(18) 0.0280(8) Uani 1 1 d . . . . .
N4 N 0.2686(3) 0.3973(3) 0.55476(19) 0.0347(9) Uani 1 1 d . . . . .
N5 N 0.1770(3) 0.4920(3) 0.5627(2) 0.0367(9) Uani 1 1 d . . . . .
N6 N 0.1723(3) 0.5130(3) 0.63026(19) 0.0303(8) Uani 1 1 d . . . . .
N13 N 0.6926(4) 0.2230(4) 0.6272(2) 0.0390(9) Uani 1 1 d . . . . .
N14 N 0.4220(3) 0.1724(3) 0.5144(2) 0.0318(8) Uani 1 1 d . . . . .
N15 N 0.2677(3) 0.1061(3) 0.7539(2) 0.0330(8) Uani 1 1 d . . . . .
C1 C 0.4381(4) 0.2857(4) 0.8225(2) 0.0292(9) Uani 1 1 d . . . . .
C2 C 0.3904(4) 0.3601(4) 0.8713(3) 0.0359(10) Uani 1 1 d . . . . .
H2 H 0.421492 0.340275 0.918556 0.043 Uiso 1 1 calc R . . . .
C3 C 0.2968(4) 0.4640(4) 0.8520(2) 0.0385(11) Uani 1 1 d D . . . .
C4 C 0.2530(4) 0.4859(4) 0.7829(2) 0.0341(10) Uani 1 1 d . . . . .
H4 H 0.188551 0.554883 0.767298 0.041 Uiso 1 1 calc R . . . .
C5 C 0.3031(4) 0.4073(4) 0.7371(2) 0.0292(9) Uani 1 1 d . . . . .
C6 C 0.5430(4) 0.1764(4) 0.8389(2) 0.0301(9) Uani 1 1 d . . . . .
C7 C 0.5966(4) 0.1386(4) 0.9058(2) 0.0339(10) Uani 1 1 d . . . . .
H7 H 0.564872 0.182307 0.943540 0.041 Uiso 1 1 calc R . . . .
C8 C 0.6967(4) 0.0373(4) 0.9189(2) 0.0327(10) Uani 1 1 d . . . . .
C9 C 0.7395(4) -0.0201(4) 0.8607(3) 0.0380(11) Uani 1 1 d . . . . .
H9 H 0.808368 -0.088277 0.865842 0.046 Uiso 1 1 calc R . . . .
C10 C 0.6829(4) 0.0211(4) 0.7959(3) 0.0377(11) Uani 1 1 d . . . . .
H10 H 0.714071 -0.021166 0.757449 0.045 Uiso 1 1 calc R . . . .
C11 C 0.2662(4) 0.4261(4) 0.6626(2) 0.0284(9) Uani 1 1 d . . . . .
C12A C 0.2475(12) 0.5539(13) 0.9008(8) 0.048(3) Uani 0.5 1 d D U P A 1
C12B C 0.2414(11) 0.5406(13) 0.9105(8) 0.050(4) Uani 0.5 1 d D U P A 2
C13 C 0.3469(5) 0.5589(4) 0.9441(3) 0.0496(13) Uani 1 1 d D . . . .
H13A H 0.409031 0.579365 0.910767 0.074 Uiso 0.5 1 calc R . P A 1
H13B H 0.311771 0.616768 0.975402 0.074 Uiso 0.5 1 calc R . P A 1
H13C H 0.384339 0.483853 0.974027 0.074 Uiso 0.5 1 calc R . P A 1
H13D H 0.404566 0.484388 0.964652 0.074 Uiso 0.5 1 calc R . P A 2
H13E H 0.388999 0.598874 0.906351 0.074 Uiso 0.5 1 calc R . P A 2
H13F H 0.313967 0.605016 0.982458 0.074 Uiso 0.5 1 calc R . P A 2
C14A C 0.1932(13) 0.6745(12) 0.8583(8) 0.052(3) Uani 0.5 1 d D U P A 1
H14A H 0.257288 0.696256 0.827835 0.078 Uiso 0.5 1 calc GR . P A 1
H14B H 0.157704 0.728385 0.892230 0.078 Uiso 0.5 1 calc GR . P A 1
H14C H 0.129500 0.676560 0.827605 0.078 Uiso 0.5 1 calc GR . P A 1
C14B C 0.1465(13) 0.6551(13) 0.8768(8) 0.063(4) Uani 0.5 1 d D U P A 2
H14D H 0.185857 0.695080 0.837400 0.094 Uiso 0.5 1 calc GR . P A 2
H14E H 0.113107 0.703220 0.914149 0.094 Uiso 0.5 1 calc GR . P A 2
H14F H 0.080402 0.639541 0.857571 0.094 Uiso 0.5 1 calc GR . P A 2
C15A C 0.1525(15) 0.5223(12) 0.9526(9) 0.056(4) Uani 0.5 1 d D U P A 1
H15A H 0.087804 0.518753 0.924977 0.084 Uiso 0.5 1 calc GR . P A 1
H15B H 0.117615 0.580346 0.983858 0.084 Uiso 0.5 1 calc GR . P A 1
H15C H 0.190327 0.447420 0.982610 0.084 Uiso 0.5 1 calc GR . P A 1
C15B C 0.1727(14) 0.4777(12) 0.9692(8) 0.050(3) Uani 0.5 1 d D U P A 2
H15D H 0.117356 0.453435 0.945744 0.074 Uiso 0.5 1 calc GR . P A 2
H15E H 0.125708 0.529719 1.002339 0.074 Uiso 0.5 1 calc GR . P A 2
H15F H 0.231807 0.410341 0.996614 0.074 Uiso 0.5 1 calc GR . P A 2
C16 C 0.7511(4) -0.0069(4) 0.9939(2) 0.0368(10) Uani 1 1 d . . . . .
C17 C 0.7705(5) 0.0894(5) 1.0237(3) 0.0497(13) Uani 1 1 d . . . . .
H17A H 0.833573 0.113984 0.993903 0.075 Uiso 1 1 calc GR . . . .
H17B H 0.796324 0.061724 1.073872 0.075 Uiso 1 1 calc GR . . . .
H17C H 0.694055 0.154369 1.022381 0.075 Uiso 1 1 calc GR . . . .
C18 C 0.6593(5) -0.0514(5) 1.0441(3) 0.0467(13) Uani 1 1 d . . . . .
H18A H 0.582381 0.011896 1.047500 0.070 Uiso 1 1 calc GR . . . .
H18B H 0.692285 -0.082820 1.092533 0.070 Uiso 1 1 calc GR . . . .
H18C H 0.644600 -0.111490 1.024308 0.070 Uiso 1 1 calc GR . . . .
C19 C 0.8729(5) -0.1054(5) 0.9925(3) 0.0588(16) Uani 1 1 d . . . . .
H19A H 0.859458 -0.171094 0.979025 0.088 Uiso 1 1 calc GR . . . .
H19B H 0.907344 -0.127655 1.040724 0.088 Uiso 1 1 calc GR . . . .
H19C H 0.929581 -0.080231 0.956941 0.088 Uiso 1 1 calc GR . . . .
N7 N -0.0514(3) 0.7289(3) 0.49947(19) 0.0285(8) Uani 1 1 d . . . . .
N8 N 0.0937(3) 0.5675(3) 0.4254(2) 0.0304(8) Uani 1 1 d . . . . .
H8 H 0.087370 0.559681 0.473010 0.036 Uiso 1 1 calc R . . . .
N9 N -0.0306(3) 0.6902(3) 0.65519(18) 0.0305(8) Uani 1 1 d . . . . .
H9A H 0.033761 0.641253 0.636882 0.037 Uiso 1 1 calc R . . . .
N10 N -0.0616(3) 0.6880(3) 0.7262(2) 0.0338(8) Uani 1 1 d . . . . .
N11 N -0.1628(3) 0.7735(3) 0.7308(2) 0.0377(9) Uani 1 1 d . . . . .
N12 N -0.1961(3) 0.8324(3) 0.6627(2) 0.0329(8) Uani 1 1 d . . . . .
C20 C -0.0414(4) 0.7600(4) 0.4271(2) 0.0291(9) Uani 1 1 d . . . . .
C21 C -0.0836(4) 0.8727(4) 0.3924(2) 0.0308(9) Uani 1 1 d . . . . .
H21 H -0.074271 0.889825 0.341052 0.037 Uiso 1 1 calc R . . . .
C22 C -0.1393(4) 0.9614(3) 0.4314(2) 0.0284(9) Uani 1 1 d . . . . .
C23 C -0.1525(4) 0.9288(4) 0.5065(2) 0.0305(9) Uani 1 1 d . . . . .
H23 H -0.192288 0.984726 0.536330 0.037 Uiso 1 1 calc R . . . .
C24 C -0.1068(4) 0.8137(4) 0.5368(2) 0.0290(9) Uani 1 1 d . . . . .
C25 C 0.0273(4) 0.6673(4) 0.3856(2) 0.0298(9) Uani 1 1 d . . . . .
C26 C 0.0361(4) 0.6780(4) 0.3112(2) 0.0330(10) Uani 1 1 d . . . . .
H26 H -0.014032 0.745998 0.282755 0.040 Uiso 1 1 calc R . . . .
C27 C 0.1166(4) 0.5917(4) 0.2766(2) 0.0316(9) Uani 1 1 d . . . . .
C28 C 0.1836(4) 0.4902(4) 0.3205(2) 0.0352(10) Uani 1 1 d . . . . .
H28 H 0.238717 0.428742 0.299050 0.042 Uiso 1 1 calc R . . . .
C29 C 0.1694(4) 0.4796(4) 0.3947(2) 0.0349(10) Uani 1 1 d . . . . .
H29 H 0.213167 0.409936 0.424493 0.042 Uiso 1 1 calc R . . . .
C30 C -0.1142(4) 0.7796(4) 0.6166(2) 0.0299(9) Uani 1 1 d . . . . .
C31 C -0.1834(4) 1.0857(4) 0.3929(2) 0.0297(9) Uani 1 1 d . . . . .
C32 C -0.3104(4) 1.1119(4) 0.3640(3) 0.0385(11) Uani 1 1 d . . . . .
H32A H -0.366845 1.100547 0.404635 0.058 Uiso 1 1 calc GR . . . .
H32B H -0.304919 1.060395 0.330080 0.058 Uiso 1 1 calc GR . . . .
H32C H -0.340140 1.191589 0.338846 0.058 Uiso 1 1 calc GR . . . .
C33 C -0.0955(5) 1.1044(4) 0.3284(3) 0.0403(11) Uani 1 1 d . . . . .
H33A H -0.119489 1.186203 0.307663 0.060 Uiso 1 1 calc GR . . . .
H33B H -0.098939 1.061109 0.291273 0.060 Uiso 1 1 calc GR . . . .
H33C H -0.012184 1.077877 0.345381 0.060 Uiso 1 1 calc GR . . . .
C34 C -0.1940(4) 1.1687(4) 0.4445(2) 0.0349(10) Uani 1 1 d . . . . .
H34A H -0.215478 1.247011 0.417131 0.052 Uiso 1 1 calc GR . . . .
H34B H -0.115864 1.148064 0.467236 0.052 Uiso 1 1 calc GR . . . .
H34C H -0.257496 1.164073 0.482060 0.052 Uiso 1 1 calc GR . . . .
C35 C 0.1311(4) 0.6104(4) 0.1937(3) 0.0401(11) Uani 1 1 d . . . . .
C36 C 0.0096(5) 0.6296(5) 0.1629(3) 0.0554(15) Uani 1 1 d . . . . .
H36A H -0.016062 0.562840 0.181146 0.083 Uiso 1 1 calc GR . . . .
H36B H 0.017757 0.640444 0.109779 0.083 Uiso 1 1 calc GR . . . .
H36C H -0.051624 0.698027 0.177744 0.083 Uiso 1 1 calc GR . . . .
C37 C 0.1717(6) 0.7160(5) 0.1692(3) 0.0634(17) Uani 1 1 d . . . . .
H37A H 0.106107 0.784620 0.180389 0.095 Uiso 1 1 calc GR . . . .
H37B H 0.190275 0.725123 0.116755 0.095 Uiso 1 1 calc GR . . . .
H37C H 0.244703 0.705536 0.194764 0.095 Uiso 1 1 calc GR . . . .
C38 C 0.2281(5) 0.5085(4) 0.1662(3) 0.0483(13) Uani 1 1 d . . . . .
H38A H 0.306541 0.495083 0.186736 0.072 Uiso 1 1 calc GR . . . .
H38B H 0.235669 0.525057 0.113143 0.072 Uiso 1 1 calc GR . . . .
H38C H 0.204300 0.440035 0.181166 0.072 Uiso 1 1 calc GR . . . .
N16 N 0.5675(6) -0.2644(4) 0.9452(3) 0.0719(16) Uani 1 1 d . . . . .
C39 C 0.5528(5) -0.2462(4) 0.8849(3) 0.0488(13) Uani 1 1 d . . . . .
C40 C 0.5349(6) -0.2220(5) 0.8076(3) 0.0550(14) Uani 1 1 d . . . . .
H40A H 0.609861 -0.216153 0.781352 0.083 Uiso 1 1 calc GR . . . .
H40B H 0.468044 -0.149415 0.795534 0.083 Uiso 1 1 calc GR . . . .
H40C H 0.514686 -0.283953 0.793663 0.083 Uiso 1 1 calc GR . . . .
N17 N 0.5027(5) 0.4261(5) 0.2816(3) 0.0679(14) Uani 1 1 d . . . . .
C41 C 0.5031(5) 0.4325(4) 0.3410(4) 0.0513(14) Uani 1 1 d . . . . .
C42 C 0.5027(5) 0.4397(5) 0.4172(3) 0.0571(15) Uani 1 1 d . . . . .
H42A H 0.578301 0.450003 0.427149 0.086 Uiso 1 1 calc GR . . . .
H42B H 0.496571 0.368944 0.447228 0.086 Uiso 1 1 calc GR . . . .
H42C H 0.432764 0.505076 0.428626 0.086 Uiso 1 1 calc GR . . . .


_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
Eu01 O1 2.529(3) . ?
Eu01 O2 2.440(3) . ?
Eu01 O4 2.511(3) . ?
Eu01 O5 2.538(3) . ?
Eu01 O7 2.539(3) . ?
Eu01 O8 2.570(3) . ?
Eu01 O10 2.421(3) . ?
Eu01 N1 2.565(3) . ?
Eu01 N2 2.558(3) . ?
Eu01 N3 2.480(3) . ?
Eu01 N13 2.908(4) . ?
Eu01 N14 2.944(4) . ?
O1 N13 1.264(5) . ?
O2 N13 1.280(5) . ?
O3 N13 1.221(5) . ?
O4 N14 1.271(4) . ?
O5 N14 1.272(5) . ?
O6 N14 1.230(4) . ?
O7 N15 1.266(5) . ?
O8 N15 1.259(5) . ?
O9 N15 1.229(5) . ?
O10 H10A 0.8855 . ?
O10 H10B 0.8861 . ?
N1 C1 1.351(5) . ?
N1 C5 1.352(5) . ?
N2 C6 1.355(5) . ?
N2 C10 1.349(5) . ?
N3 N4 1.319(5) . ?
N3 C11 1.333(5) . ?
N4 N5 1.322(5) . ?
N5 N6 1.340(5) . ?
N6 C11 1.349(5) . ?
C1 C2 1.379(6) . ?
C1 C6 1.497(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.396(6) . ?
C3 C4 1.388(6) . ?
C3 C12A 1.519(11) . ?
C3 C12B 1.549(11) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(6) . ?
C5 C11 1.458(6) . ?
C6 C7 1.387(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.402(6) . ?
C8 C9 1.384(6) . ?
C8 C16 1.529(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.369(6) . ?
C10 H10 0.9500 . ?
C12A C13 1.513(11) . ?
C12A C14A 1.523(12) . ?
C12A C15A 1.508(12) . ?
C12B C13 1.548(11) . ?
C12B C14B 1.547(11) . ?
C12B C15B 1.553(12) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 H13D 0.9800 . ?
C13 H13E 0.9800 . ?
C13 H13F 0.9800 . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
C16 C17 1.527(7) . ?
C16 C18 1.537(7) . ?
C16 C19 1.533(7) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
N7 C20 1.344(6) . ?
N7 C24 1.334(5) . ?
N8 H8 0.8800 . ?
N8 C25 1.349(5) . ?
N8 C29 1.346(5) . ?
N9 H9A 0.8800 . ?
N9 N10 1.345(5) . ?
N9 C30 1.347(5) . ?
N10 N11 1.305(5) . ?
N11 N12 1.367(5) . ?
N12 C30 1.313(5) . ?
C20 C21 1.382(6) . ?
C20 C25 1.483(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.391(6) . ?
C22 C23 1.401(6) . ?
C22 C31 1.524(6) . ?
C23 H23 0.9500 . ?
C23 C24 1.385(6) . ?
C24 C30 1.480(6) . ?
C25 C26 1.375(6) . ?
C26 H26 0.9500 . ?
C26 C27 1.392(6) . ?
C27 C28 1.399(6) . ?
C27 C35 1.531(6) . ?
C28 H28 0.9500 . ?
C28 C29 1.373(6) . ?
C29 H29 0.9500 . ?
C31 C32 1.539(6) . ?
C31 C33 1.544(6) . ?
C31 C34 1.530(6) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C36 1.515(7) . ?
C35 C37 1.540(7) . ?
C35 C38 1.529(7) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
N16 C39 1.131(7) . ?
C39 C40 1.446(8) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
N17 C41 1.137(7) . ?
C41 C42 1.453(8) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 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
O1 Eu01 O5 110.70(10) . . ?
O1 Eu01 O7 125.72(10) . . ?
O1 Eu01 O8 174.32(10) . . ?
O1 Eu01 N1 112.87(10) . . ?
O1 Eu01 N2 71.67(11) . . ?
O1 Eu01 N13 25.69(10) . . ?
O1 Eu01 N14 90.45(10) . . ?
O2 Eu01 O1 51.50(10) . . ?
O2 Eu01 O4 74.74(10) . . ?
O2 Eu01 O5 122.77(10) . . ?
O2 Eu01 O7 143.14(10) . . ?
O2 Eu01 O8 133.97(10) . . ?
O2 Eu01 N1 71.91(10) . . ?
O2 Eu01 N2 77.10(11) . . ?
O2 Eu01 N3 74.57(11) . . ?
O2 Eu01 N13 25.85(10) . . ?
O2 Eu01 N14 98.24(11) . . ?
O4 Eu01 O1 68.41(10) . . ?
O4 Eu01 O5 50.75(9) . . ?
O4 Eu01 O7 141.91(10) . . ?
O4 Eu01 O8 113.23(10) . . ?
O4 Eu01 N1 131.47(10) . . ?
O4 Eu01 N2 139.80(11) . . ?
O4 Eu01 N13 68.52(10) . . ?
O4 Eu01 N14 25.38(10) . . ?
O5 Eu01 O7 93.46(10) . . ?
O5 Eu01 O8 68.33(10) . . ?
O5 Eu01 N1 130.56(10) . . ?
O5 Eu01 N2 157.36(11) . . ?
O5 Eu01 N13 118.82(10) . . ?
O5 Eu01 N14 25.49(10) . . ?
O7 Eu01 O8 49.49(10) . . ?
O7 Eu01 N1 79.49(11) . . ?
O7 Eu01 N2 69.13(11) . . ?
O7 Eu01 N13 141.06(11) . . ?
O7 Eu01 N14 118.50(11) . . ?
O8 Eu01 N13 159.82(11) . . ?
O8 Eu01 N14 90.04(10) . . ?
O10 Eu01 O1 69.70(10) . . ?
O10 Eu01 O2 121.11(10) . . ?
O10 Eu01 O4 81.89(10) . . ?
O10 Eu01 O5 71.89(10) . . ?
O10 Eu01 O7 73.43(10) . . ?
O10 Eu01 O8 104.90(10) . . ?
O10 Eu01 N1 146.12(11) . . ?
O10 Eu01 N2 88.81(10) . . ?
O10 Eu01 N3 145.62(10) . . ?
O10 Eu01 N13 95.27(11) . . ?
O10 Eu01 N14 77.27(10) . . ?
N1 Eu01 O8 70.46(10) . . ?
N1 Eu01 N13 93.12(11) . . ?
N1 Eu01 N14 134.80(10) . . ?
N2 Eu01 O8 106.97(11) . . ?
N2 Eu01 N1 62.33(11) . . ?
N2 Eu01 N13 73.58(12) . . ?
N2 Eu01 N14 160.44(11) . . ?
N3 Eu01 O1 119.36(11) . . ?
N3 Eu01 O4 72.90(10) . . ?
N3 Eu01 O5 74.08(10) . . ?
N3 Eu01 O7 113.70(11) . . ?
N3 Eu01 O8 66.06(11) . . ?
N3 Eu01 N1 64.95(11) . . ?
N3 Eu01 N2 125.50(11) . . ?
N3 Eu01 N13 96.76(12) . . ?
N3 Eu01 N14 69.89(10) . . ?
N13 Eu01 N14 93.85(11) . . ?
N13 O1 Eu01 94.1(2) . . ?
N13 O2 Eu01 97.9(2) . . ?
N14 O4 Eu01 96.7(2) . . ?
N14 O5 Eu01 95.4(2) . . ?
N15 O7 Eu01 98.0(2) . . ?
N15 O8 Eu01 96.7(2) . . ?
Eu01 O10 H10A 111.2 . . ?
Eu01 O10 H10B 111.0 . . ?
H10A O10 H10B 107.7 . . ?
C1 N1 Eu01 123.4(3) . . ?
C1 N1 C5 116.9(3) . . ?
C5 N1 Eu01 119.7(3) . . ?
C6 N2 Eu01 122.7(3) . . ?
C10 N2 Eu01 119.9(3) . . ?
C10 N2 C6 116.7(4) . . ?
N4 N3 Eu01 133.0(3) . . ?
N4 N3 C11 106.5(3) . . ?
C11 N3 Eu01 118.0(3) . . ?
N3 N4 N5 108.7(3) . . ?
N4 N5 N6 110.0(3) . . ?
N5 N6 C11 104.2(3) . . ?
O1 N13 Eu01 60.2(2) . . ?
O1 N13 O2 116.3(4) . . ?
O2 N13 Eu01 56.2(2) . . ?
O3 N13 Eu01 175.2(4) . . ?
O3 N13 O1 122.3(4) . . ?
O3 N13 O2 121.4(4) . . ?
O4 N14 Eu01 57.89(19) . . ?
O4 N14 O5 116.6(3) . . ?
O5 N14 Eu01 59.13(19) . . ?
O6 N14 Eu01 173.5(3) . . ?
O6 N14 O4 121.8(4) . . ?
O6 N14 O5 121.6(4) . . ?
O7 N15 Eu01 57.2(2) . . ?
O8 N15 Eu01 58.6(2) . . ?
O8 N15 O7 115.8(3) . . ?
O9 N15 Eu01 177.4(3) . . ?
O9 N15 O7 122.0(4) . . ?
O9 N15 O8 122.1(4) . . ?
N1 C1 C2 122.3(4) . . ?
N1 C1 C6 114.8(4) . . ?
C2 C1 C6 123.0(4) . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.8(4) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 C12A 123.4(7) . . ?
C2 C3 C12B 118.5(6) . . ?
C4 C3 C2 116.6(4) . . ?
C4 C3 C12A 119.9(7) . . ?
C4 C3 C12B 124.6(6) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.8(4) . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 123.5(4) . . ?
N1 C5 C11 113.2(4) . . ?
C4 C5 C11 123.2(4) . . ?
N2 C6 C1 115.6(4) . . ?
N2 C6 C7 121.6(4) . . ?
C7 C6 C1 122.7(4) . . ?
C6 C7 H7 119.3 . . ?
C6 C7 C8 121.3(4) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 C16 120.9(4) . . ?
C9 C8 C7 115.9(4) . . ?
C9 C8 C16 123.2(4) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.3(4) . . ?
C10 C9 H9 119.8 . . ?
N2 C10 C9 124.2(4) . . ?
N2 C10 H10 117.9 . . ?
C9 C10 H10 117.9 . . ?
N3 C11 N6 110.5(4) . . ?
N3 C11 C5 122.3(4) . . ?
N6 C11 C5 127.2(4) . . ?
C3 C12A C14A 112.6(11) . . ?
C13 C12A C3 111.7(8) . . ?
C13 C12A C14A 105.3(11) . . ?
C15A C12A C3 107.9(11) . . ?
C15A C12A C13 109.0(12) . . ?
C15A C12A C14A 110.3(10) . . ?
C3 C12B C15B 108.1(10) . . ?
C13 C12B C3 108.2(8) . . ?
C13 C12B C15B 110.6(11) . . ?
C14B C12B C3 110.3(10) . . ?
C14B C12B C13 112.3(11) . . ?
C14B C12B C15B 107.3(10) . . ?
C12A C13 H13A 109.5 . . ?
C12A C13 H13B 109.5 . . ?
C12A C13 H13C 109.5 . . ?
C12B C13 H13D 109.5 . . ?
C12B C13 H13E 109.5 . . ?
C12B C13 H13F 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
H13D C13 H13E 109.5 . . ?
H13D C13 H13F 109.5 . . ?
H13E C13 H13F 109.5 . . ?
C12A C14A H14A 109.5 . . ?
C12A C14A H14B 109.5 . . ?
C12A C14A H14C 109.5 . . ?
H14A C14A H14B 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C12B C14B H14D 109.5 . . ?
C12B C14B H14E 109.5 . . ?
C12B C14B H14F 109.5 . . ?
H14D C14B H14E 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C12A C15A H15A 109.5 . . ?
C12A C15A H15B 109.5 . . ?
C12A C15A H15C 109.5 . . ?
H15A C15A H15B 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C12B C15B H15D 109.5 . . ?
C12B C15B H15E 109.5 . . ?
C12B C15B H15F 109.5 . . ?
H15D C15B H15E 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C8 C16 C18 107.1(4) . . ?
C8 C16 C19 112.0(4) . . ?
C17 C16 C8 110.8(4) . . ?
C17 C16 C18 109.3(4) . . ?
C17 C16 C19 108.9(4) . . ?
C19 C16 C18 108.7(4) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C24 N7 C20 116.1(4) . . ?
C25 N8 H8 118.9 . . ?
C29 N8 H8 118.9 . . ?
C29 N8 C25 122.3(4) . . ?
N10 N9 H9A 125.6 . . ?
N10 N9 C30 108.9(4) . . ?
C30 N9 H9A 125.6 . . ?
N11 N10 N9 106.7(3) . . ?
N10 N11 N12 109.6(3) . . ?
C30 N12 N11 107.0(3) . . ?
N7 C20 C21 123.0(4) . . ?
N7 C20 C25 116.5(4) . . ?
C21 C20 C25 120.4(4) . . ?
C20 C21 H21 119.5 . . ?
C20 C21 C22 121.0(4) . . ?
C22 C21 H21 119.5 . . ?
C21 C22 C23 116.0(4) . . ?
C21 C22 C31 120.8(4) . . ?
C23 C22 C31 123.3(4) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 C22 119.1(4) . . ?
C24 C23 H23 120.5 . . ?
N7 C24 C23 124.8(4) . . ?
N7 C24 C30 115.9(4) . . ?
C23 C24 C30 119.2(4) . . ?
N8 C25 C20 115.7(4) . . ?
N8 C25 C26 118.4(4) . . ?
C26 C25 C20 125.7(4) . . ?
C25 C26 H26 119.2 . . ?
C25 C26 C27 121.6(4) . . ?
C27 C26 H26 119.2 . . ?
C26 C27 C28 117.4(4) . . ?
C26 C27 C35 120.1(4) . . ?
C28 C27 C35 122.5(4) . . ?
C27 C28 H28 120.1 . . ?
C29 C28 C27 119.9(4) . . ?
C29 C28 H28 120.1 . . ?
N8 C29 C28 120.2(4) . . ?
N8 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
N9 C30 C24 124.5(4) . . ?
N12 C30 N9 107.8(4) . . ?
N12 C30 C24 127.6(4) . . ?
C22 C31 C32 108.3(3) . . ?
C22 C31 C33 110.3(4) . . ?
C22 C31 C34 111.6(4) . . ?
C32 C31 C33 109.0(4) . . ?
C34 C31 C32 108.4(3) . . ?
C34 C31 C33 109.2(4) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C27 C35 C37 107.7(4) . . ?
C36 C35 C27 108.5(4) . . ?
C36 C35 C37 111.1(5) . . ?
C36 C35 C38 109.3(4) . . ?
C38 C35 C27 112.3(4) . . ?
C38 C35 C37 107.9(4) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N16 C39 C40 179.2(7) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
N17 C41 C42 179.2(7) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?

_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_jk400
_database_code_depnum_ccdc_archive 'CCDC 1550717'
_audit_update_record             
;
2017-05-17 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;
_audit_creation_date             2017-05-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6

#==============================================================================

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl, C19 H25 N6'
_chemical_formula_sum            'C19 H25 Cl N6'
_chemical_formula_weight         372.90
_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 0.0030 0.0020 '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'
Cl Cl 0.1480 0.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.0538(11)
_cell_length_b                   14.4067(9)
_cell_length_c                   13.0173(11)
_cell_angle_alpha                90
_cell_angle_beta                 103.335(7)
_cell_angle_gamma                90
_cell_volume                     2017.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7776
_cell_measurement_temperature    190
_cell_measurement_theta_max      26.94
_cell_measurement_theta_min      1.41
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.093
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_unetI/netI     0.0718
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13867
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.179
_diffrn_reflns_theta_min         2.141
_diffrn_ambient_temperature      190
_diffrn_detector                 'image plate (34cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5mm monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube, 12x0.4mm long-fine focus'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2554
_reflns_number_total             4475
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
PLATON (A.L.Spek, 2009)
;
_computing_data_reduction        
;
X-Area Integrate 1.71.0.0 (STOE, 2016)
X-Area LANA 1.70.0.0 (STOE, 2017)
PLATON (A.L.Spek, 2009)
;
_computing_structure_solution    'SHELXS-2016/6 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_molecular_graphics    'Diamond 4, Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.77, Darmstadt 2016
MS Word (Microsoft)
Olex2 (Dolomanov et al., 2009)
;
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4475
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1193
_refine_ls_R_factor_gt           0.0541
_refine_ls_restrained_S_all      1.011
_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)+(0.0483P)²+0.8660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1283
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
Cl Cl 0.22173(7) 0.42592(5) 0.74124(6) 0.0519(2) Uani 1 1 d . . . . .
C4 C 0.2304(2) 0.07481(18) 0.47960(19) 0.0335(6) Uani 1 1 d . . . . .
N2 N -0.18189(19) 0.21205(15) 0.42630(15) 0.0327(5) Uani 1 1 d . . . . .
N3 N -0.0339(2) -0.04294(16) 0.29671(17) 0.0438(6) Uani 1 1 d . . . . .
C3 C 0.2558(2) 0.15544(17) 0.53974(18) 0.0320(6) Uani 1 1 d . . . . .
N1 N 0.01277(18) 0.11126(14) 0.42961(14) 0.0316(5) Uani 1 1 d . . . . .
C11 C 0.0778(2) -0.02632(17) 0.35919(18) 0.0352(6) Uani 1 1 d . . . . .
C7 C -0.0812(2) 0.32233(17) 0.54936(19) 0.0308(6) Uani 1 1 d . . . . .
N6 N 0.1541(2) -0.09546(14) 0.35045(16) 0.0428(6) Uani 1 1 d . . . . .
C9 C -0.2994(2) 0.33259(19) 0.47626(19) 0.0372(6) Uani 1 1 d . . . . .
C5 C 0.1088(2) 0.05636(16) 0.42632(17) 0.0317(6) Uani 1 1 d . . . . .
N4 N -0.0284(3) -0.12439(16) 0.24740(17) 0.0528(7) Uani 1 1 d . . . . .
C6 C -0.0756(2) 0.24419(16) 0.49001(17) 0.0292(5) Uani 1 1 d . . . . .
C2 C 0.1551(2) 0.21240(17) 0.54424(18) 0.0315(6) Uani 1 1 d . . . . .
C1 C 0.0364(2) 0.18827(16) 0.48917(17) 0.0289(5) Uani 1 1 d . . . . .
C12 C 0.3870(2) 0.18235(18) 0.5985(2) 0.0382(6) Uani 1 1 d . . . . .
N5 N 0.0849(3) -0.15545(16) 0.27975(18) 0.0517(7) Uani 1 1 d . . . . .
C8 C -0.1937(2) 0.36878(17) 0.54482(17) 0.0322(6) Uani 1 1 d . . . . .
C19 C -0.3307(3) 0.4943(3) 0.5935(3) 0.0509(8) Uani 1 1 d . . . . .
C16 C -0.1991(2) 0.45400(18) 0.61250(19) 0.0358(6) Uani 1 1 d . . . . .
C17 C -0.1555(4) 0.4253(3) 0.7289(2) 0.0566(9) Uani 1 1 d . . . . .
C10 C -0.2908(2) 0.25450(19) 0.4181(2) 0.0386(6) Uani 1 1 d . . . . .
C18 C -0.1134(3) 0.5286(2) 0.5857(3) 0.0498(8) Uani 1 1 d . . . . .
C14 C 0.4157(3) 0.2799(3) 0.5642(3) 0.0593(9) Uani 1 1 d . . . . .
C15 C 0.3918(3) 0.1834(3) 0.7166(2) 0.0541(9) Uani 1 1 d . . . . .
C13 C 0.4843(3) 0.1148(3) 0.5767(3) 0.0621(10) Uani 1 1 d . . . . .
H2 H -0.179(3) 0.159(2) 0.383(2) 0.062(9) Uiso 1 1 d . . . . .
H3 H -0.108(3) -0.010(2) 0.283(2) 0.069(11) Uiso 1 1 d . . . . .
H7 H -0.010(2) 0.3443(16) 0.5942(18) 0.033(7) Uiso 1 1 d . . . . .
H18A H -0.023(3) 0.510(2) 0.602(2) 0.056(9) Uiso 1 1 d . . . . .
H2A H 0.1664(19) 0.2658(16) 0.5857(17) 0.021(6) Uiso 1 1 d . . . . .
H14A H 0.500(3) 0.297(2) 0.601(2) 0.066(9) Uiso 1 1 d . . . . .
H10 H -0.359(3) 0.226(2) 0.372(2) 0.055(8) Uiso 1 1 d . . . . .
H15A H 0.473(3) 0.2018(19) 0.757(2) 0.053(8) Uiso 1 1 d . . . . .
H17A H -0.167(3) 0.479(2) 0.772(2) 0.072(10) Uiso 1 1 d . . . . .
H18B H -0.122(3) 0.584(2) 0.626(2) 0.053(8) Uiso 1 1 d . . . . .
H9 H -0.378(2) 0.3611(18) 0.4682(19) 0.042(7) Uiso 1 1 d . . . . .
H4 H 0.295(2) 0.0316(17) 0.4764(18) 0.035(7) Uiso 1 1 d . . . . .
H13A H 0.467(3) 0.044(2) 0.605(2) 0.071(10) Uiso 1 1 d . . . . .
H13B H 0.565(3) 0.133(2) 0.617(2) 0.068(10) Uiso 1 1 d . . . . .
H15B H 0.332(3) 0.229(2) 0.732(2) 0.065(10) Uiso 1 1 d . . . . .
H17B H -0.068(4) 0.408(2) 0.745(3) 0.079(11) Uiso 1 1 d . . . . .
H14B H 0.354(3) 0.329(2) 0.585(3) 0.086(12) Uiso 1 1 d . . . . .
H13C H 0.481(3) 0.117(2) 0.503(3) 0.070(11) Uiso 1 1 d . . . . .
H18C H -0.137(3) 0.544(2) 0.510(3) 0.067(10) Uiso 1 1 d . . . . .
H19A H -0.362(3) 0.508(2) 0.519(3) 0.078(11) Uiso 1 1 d . . . . .
H19B H -0.389(4) 0.452(3) 0.615(3) 0.089(12) Uiso 1 1 d . . . . .
H14C H 0.413(3) 0.281(2) 0.491(3) 0.077(12) Uiso 1 1 d . . . . .
H19C H -0.326(2) 0.549(2) 0.638(2) 0.043(8) Uiso 1 1 d . . . . .
H17C H -0.209(3) 0.377(3) 0.745(3) 0.085(13) Uiso 1 1 d . . . . .
H15C H 0.371(3) 0.118(3) 0.743(3) 0.081(11) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C4 C3 1.393(3) . ?
C4 C5 1.389(3) . ?
C4 H4 0.96(2) . ?
N2 C6 1.354(3) . ?
N2 C10 1.333(3) . ?
N2 H2 0.96(3) . ?
N3 C11 1.334(3) . ?
N3 N4 1.346(3) . ?
N3 H3 0.93(3) . ?
C3 C2 1.396(3) . ?
C3 C12 1.525(3) . ?
N1 C5 1.332(3) . ?
N1 C1 1.344(3) . ?
C11 N6 1.327(3) . ?
C11 C5 1.470(3) . ?
C7 C6 1.375(3) . ?
C7 C8 1.402(3) . ?
C7 H7 0.92(2) . ?
N6 N5 1.362(3) . ?
C9 C8 1.397(3) . ?
C9 C10 1.371(4) . ?
C9 H9 0.95(3) . ?
N4 N5 1.305(3) . ?
C6 C1 1.479(3) . ?
C2 C1 1.386(3) . ?
C2 H2A 0.93(2) . ?
C12 C14 1.531(4) . ?
C12 C15 1.526(4) . ?
C12 C13 1.526(4) . ?
C8 C16 1.520(3) . ?
C19 C16 1.533(4) . ?
C19 H19A 0.98(3) . ?
C19 H19B 0.97(4) . ?
C19 H19C 0.97(3) . ?
C16 C17 1.537(4) . ?
C16 C18 1.525(4) . ?
C17 H17A 0.99(3) . ?
C17 H17B 0.97(4) . ?
C17 H17C 0.96(4) . ?
C10 H10 0.95(3) . ?
C18 H18A 1.00(3) . ?
C18 H18B 0.97(3) . ?
C18 H18C 0.99(3) . ?
C14 H14A 0.97(3) . ?
C14 H14B 1.06(4) . ?
C14 H14C 0.95(3) . ?
C15 H15A 0.97(3) . ?
C15 H15B 0.99(3) . ?
C15 H15C 1.05(4) . ?
C13 H13A 1.11(3) . ?
C13 H13B 0.96(3) . ?
C13 H13C 0.96(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
C3 C4 H4 120.6(15) . . ?
C5 C4 C3 119.1(2) . . ?
C5 C4 H4 120.2(15) . . ?
C6 N2 H2 119.8(18) . . ?
C10 N2 C6 122.2(2) . . ?
C10 N2 H2 118.0(18) . . ?
C11 N3 N4 108.1(3) . . ?
C11 N3 H3 133(2) . . ?
N4 N3 H3 119(2) . . ?
C4 C3 C2 117.0(2) . . ?
C4 C3 C12 122.6(2) . . ?
C2 C3 C12 120.3(2) . . ?
C5 N1 C1 117.3(2) . . ?
N3 C11 C5 124.3(2) . . ?
N6 C11 N3 109.3(2) . . ?
N6 C11 C5 126.4(2) . . ?
C6 C7 C8 121.4(2) . . ?
C6 C7 H7 119.8(15) . . ?
C8 C7 H7 118.7(15) . . ?
C11 N6 N5 105.4(2) . . ?
C8 C9 H9 121.4(16) . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 H9 118.3(16) . . ?
C4 C5 C11 121.2(2) . . ?
N1 C5 C4 123.8(2) . . ?
N1 C5 C11 115.0(2) . . ?
N5 N4 N3 106.9(2) . . ?
N2 C6 C7 118.7(2) . . ?
N2 C6 C1 114.8(2) . . ?
C7 C6 C1 126.6(2) . . ?
C3 C2 H2A 120.5(13) . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2A 119.4(13) . . ?
N1 C1 C6 113.7(2) . . ?
N1 C1 C2 122.7(2) . . ?
C2 C1 C6 123.6(2) . . ?
C3 C12 C14 108.9(2) . . ?
C3 C12 C15 108.5(2) . . ?
C3 C12 C13 112.0(2) . . ?
C15 C12 C14 108.9(3) . . ?
C13 C12 C14 109.2(3) . . ?
C13 C12 C15 109.4(3) . . ?
N4 N5 N6 110.4(2) . . ?
C7 C8 C16 120.9(2) . . ?
C9 C8 C7 116.9(2) . . ?
C9 C8 C16 122.2(2) . . ?
C16 C19 H19A 110(2) . . ?
C16 C19 H19B 113(2) . . ?
C16 C19 H19C 107.1(15) . . ?
H19A C19 H19B 108(3) . . ?
H19A C19 H19C 113(3) . . ?
H19B C19 H19C 106(3) . . ?
C8 C16 C19 112.0(2) . . ?
C8 C16 C17 108.0(2) . . ?
C8 C16 C18 109.1(2) . . ?
C19 C16 C17 109.3(3) . . ?
C18 C16 C19 108.2(2) . . ?
C18 C16 C17 110.2(3) . . ?
C16 C17 H17A 107.6(19) . . ?
C16 C17 H17B 111(2) . . ?
C16 C17 H17C 110(2) . . ?
H17A C17 H17B 109(3) . . ?
H17A C17 H17C 106(3) . . ?
H17B C17 H17C 113(3) . . ?
N2 C10 C9 120.6(2) . . ?
N2 C10 H10 115.0(17) . . ?
C9 C10 H10 124.3(17) . . ?
C16 C18 H18A 113.9(17) . . ?
C16 C18 H18B 108.3(17) . . ?
C16 C18 H18C 110.7(18) . . ?
H18A C18 H18B 109(2) . . ?
H18A C18 H18C 107(2) . . ?
H18B C18 H18C 108(2) . . ?
C12 C14 H14A 108.8(18) . . ?
C12 C14 H14B 110.2(19) . . ?
C12 C14 H14C 110(2) . . ?
H14A C14 H14B 108(3) . . ?
H14A C14 H14C 107(3) . . ?
H14B C14 H14C 112(3) . . ?
C12 C15 H15A 111.4(17) . . ?
C12 C15 H15B 110.1(17) . . ?
C12 C15 H15C 111.2(19) . . ?
H15A C15 H15B 106(2) . . ?
H15A C15 H15C 108(2) . . ?
H15B C15 H15C 109(3) . . ?
C12 C13 H13A 109.9(17) . . ?
C12 C13 H13B 109.3(19) . . ?
C12 C13 H13C 108(2) . . ?
H13A C13 H13B 106(2) . . ?
H13A C13 H13C 113(3) . . ?
H13B C13 H13C 111(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C3 C2 C1 -0.8(3) . . . . ?
C4 C3 C12 C14 124.9(3) . . . . ?
C4 C3 C12 C15 -116.7(3) . . . . ?
C4 C3 C12 C13 4.0(4) . . . . ?
N2 C6 C1 N1 -3.7(3) . . . . ?
N2 C6 C1 C2 176.2(2) . . . . ?
N3 C11 N6 N5 0.1(3) . . . . ?
N3 C11 C5 C4 -172.1(2) . . . . ?
N3 C11 C5 N1 6.6(3) . . . . ?
N3 N4 N5 N6 0.3(3) . . . . ?
C3 C4 C5 N1 -0.6(4) . . . . ?
C3 C4 C5 C11 178.1(2) . . . . ?
C3 C2 C1 N1 -0.5(4) . . . . ?
C3 C2 C1 C6 179.6(2) . . . . ?
C11 N3 N4 N5 -0.3(3) . . . . ?
C11 N6 N5 N4 -0.3(3) . . . . ?
C7 C6 C1 N1 175.1(2) . . . . ?
C7 C6 C1 C2 -5.0(4) . . . . ?
C7 C8 C16 C19 179.1(3) . . . . ?
C7 C8 C16 C17 -60.5(3) . . . . ?
C7 C8 C16 C18 59.3(3) . . . . ?
N6 C11 C5 C4 7.8(4) . . . . ?
N6 C11 C5 N1 -173.4(2) . . . . ?
C9 C8 C16 C19 -1.4(4) . . . . ?
C9 C8 C16 C17 119.0(3) . . . . ?
C9 C8 C16 C18 -121.2(3) . . . . ?
C5 C4 C3 C2 1.3(3) . . . . ?
C5 C4 C3 C12 -178.4(2) . . . . ?
C5 N1 C1 C6 -178.87(19) . . . . ?
C5 N1 C1 C2 1.2(3) . . . . ?
C5 C11 N6 N5 -179.9(2) . . . . ?
N4 N3 C11 N6 0.1(3) . . . . ?
N4 N3 C11 C5 -179.9(2) . . . . ?
C6 N2 C10 C9 -1.1(4) . . . . ?
C6 C7 C8 C9 -0.8(3) . . . . ?
C6 C7 C8 C16 178.8(2) . . . . ?
C2 C3 C12 C14 -54.9(3) . . . . ?
C2 C3 C12 C15 63.5(3) . . . . ?
C2 C3 C12 C13 -175.7(3) . . . . ?
C1 N1 C5 C4 -0.7(3) . . . . ?
C1 N1 C5 C11 -179.4(2) . . . . ?
C12 C3 C2 C1 178.9(2) . . . . ?
C8 C7 C6 N2 -0.1(3) . . . . ?
C8 C7 C6 C1 -178.9(2) . . . . ?
C8 C9 C10 N2 0.1(4) . . . . ?
C10 N2 C6 C7 1.1(3) . . . . ?
C10 N2 C6 C1 180.0(2) . . . . ?
C10 C9 C8 C7 0.8(4) . . . . ?
C10 C9 C8 C16 -178.7(2) . . . . ?

_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_HN4tBubipy
_database_code_depnum_ccdc_archive 'CCDC 1550718'
_audit_update_record             
;
2017-05-17 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;
_audit_creation_date             2015-04-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014/7

#==============================================================================

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'N O3, C19 H25 N6'
_chemical_formula_sum            'C19 H25 N7 O3'
_chemical_formula_weight         399.46
_chemical_absolute_configuration rmad
_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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.986(2)
_cell_length_b                   14.179(3)
_cell_length_c                   13.626(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.60(3)
_cell_angle_gamma                90
_cell_volume                     2098.7(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11173
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      29.15
_cell_measurement_theta_min      2.08
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9907
_exptl_absorpt_correction_T_min  0.9826
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'STOE X-RED & X-SHAPE'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.226
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.129
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21511
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.010
_diffrn_reflns_theta_min         2.085
_diffrn_ambient_temperature      200
_diffrn_detector                 'image plate (34cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            'STOE image plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'two-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.5mm monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube, 12x0.4mm long-fine focus'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2780
_reflns_number_total             4121
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA, PLATON (A.L.Spek, 2005)'
_computing_data_reduction        'STOE X-RED, PLATON (A.L.Spek, 2005)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 2/3, Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'MS Word, Olex2 (Dolomanov et al., 2009)'

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0591
_refine_ls_restrained_S_all      1.037
_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)+(0.0661P)²+0.3792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1402
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C2(H2a), C4(H4), C7(H7), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C13(H13a,H13b,H13c), C14(H14a,H14b,H14c), C15(H15a,H15b,H15c), C17(H17a,H17b,
 H17c), C18(H18a,H18b,H18c), C19(H19a,H19b,H19c)
;
_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
O1 O 0.71898(19) 0.04986(15) 0.69330(17) 0.0640(6) Uani 1 1 d . . . . .
O2 O 0.7671(3) 0.0229(2) 0.8485(2) 0.0950(9) Uani 1 1 d . . . . .
O3 O 0.8617(2) 0.12924(16) 0.77982(19) 0.0751(7) Uani 1 1 d . . . . .
N1 N 0.48144(17) 0.10577(13) 0.57181(14) 0.0335(4) Uani 1 1 d . . . . .
N2 N 0.67772(17) 0.21251(13) 0.57598(15) 0.0346(5) Uani 1 1 d . . . . .
H2 H 0.6729 0.1609 0.6111 0.042 Uiso 1 1 calc R . . . .
N3 N 0.5121(2) -0.05322(14) 0.69500(16) 0.0431(5) Uani 1 1 d . . . . .
H3 H 0.5789 -0.0182 0.7010 0.052 Uiso 1 1 calc R . . . .
N4 N 0.4994(2) -0.13566(15) 0.74325(18) 0.0508(6) Uani 1 1 d . . . . .
N5 N 0.3876(2) -0.16410(15) 0.71397(18) 0.0505(6) Uani 1 1 d . . . . .
N6 N 0.3265(2) -0.10256(14) 0.64731(16) 0.0438(5) Uani 1 1 d . . . . .
N7 N 0.78125(16) 0.07139(13) 0.77207(14) 0.0300(4) Uani 1 1 d . . . . .
C1 C 0.4642(2) 0.18347(15) 0.51481(17) 0.0317(5) Uani 1 1 d . . . . .
C2 C 0.3512(2) 0.20669(16) 0.46031(18) 0.0339(5) Uani 1 1 d . . . . .
H2A H 0.3431 0.2625 0.4214 0.041 Uiso 1 1 calc R . . . .
C3 C 0.2494(2) 0.14833(16) 0.46255(18) 0.0340(5) Uani 1 1 d . . . . .
C4 C 0.2682(2) 0.06724(16) 0.52090(18) 0.0360(5) Uani 1 1 d . . . . .
H4 H 0.2022 0.0247 0.5246 0.043 Uiso 1 1 calc R . . . .
C5 C 0.3839(2) 0.04941(15) 0.57342(17) 0.0328(5) Uani 1 1 d . . . . .
C6 C 0.5770(2) 0.24195(16) 0.51462(17) 0.0317(5) Uani 1 1 d . . . . .
C7 C 0.5864(2) 0.32037(15) 0.45712(17) 0.0321(5) Uani 1 1 d . . . . .
H7 H 0.5161 0.3415 0.4135 0.038 Uiso 1 1 calc R . . . .
C8 C 0.6975(2) 0.36984(15) 0.46153(18) 0.0328(5) Uani 1 1 d . . . . .
C9 C 0.7966(2) 0.33780(17) 0.52924(19) 0.0389(6) Uani 1 1 d . . . . .
H9 H 0.8728 0.3707 0.5366 0.047 Uiso 1 1 calc R . . . .
C10 C 0.7844(2) 0.25903(18) 0.5852(2) 0.0408(6) Uani 1 1 d . . . . .
H10 H 0.8525 0.2374 0.6309 0.049 Uiso 1 1 calc R . . . .
C11 C 0.4062(2) -0.03449(15) 0.63720(18) 0.0347(5) Uani 1 1 d . . . . .
C12 C 0.1237(2) 0.17479(17) 0.4047(2) 0.0420(6) Uani 1 1 d . . . . .
C13 C 0.1362(3) 0.1842(2) 0.2937(2) 0.0591(8) Uani 1 1 d . . . . .
H13A H 0.1978 0.2325 0.2857 0.089 Uiso 1 1 calc GR . . . .
H13B H 0.0567 0.2024 0.2560 0.089 Uiso 1 1 calc GR . . . .
H13C H 0.1622 0.1236 0.2690 0.089 Uiso 1 1 calc GR . . . .
C14 C 0.0859(3) 0.2703(2) 0.4425(3) 0.0696(10) Uani 1 1 d . . . . .
H14A H 0.0809 0.2659 0.5136 0.104 Uiso 1 1 calc GR . . . .
H14B H 0.0053 0.2884 0.4064 0.104 Uiso 1 1 calc GR . . . .
H14C H 0.1471 0.3180 0.4317 0.104 Uiso 1 1 calc GR . . . .
C15 C 0.0260(3) 0.1012(3) 0.4153(3) 0.0811(12) Uani 1 1 d . . . . .
H15A H 0.0527 0.0398 0.3933 0.122 Uiso 1 1 calc GR . . . .
H15B H -0.0516 0.1193 0.3744 0.122 Uiso 1 1 calc GR . . . .
H15C H 0.0138 0.0970 0.4850 0.122 Uiso 1 1 calc GR . . . .
C16 C 0.7078(2) 0.45277(16) 0.39132(19) 0.0380(6) Uani 1 1 d . . . . .
C17 C 0.6852(3) 0.4152(2) 0.2845(2) 0.0546(7) Uani 1 1 d . . . . .
H17A H 0.7464 0.3666 0.2766 0.082 Uiso 1 1 calc GR . . . .
H17B H 0.6925 0.4671 0.2382 0.082 Uiso 1 1 calc GR . . . .
H17C H 0.6024 0.3880 0.2706 0.082 Uiso 1 1 calc GR . . . .
C18 C 0.6105(3) 0.52743(18) 0.4050(2) 0.0495(7) Uani 1 1 d . . . . .
H18A H 0.5282 0.4999 0.3886 0.074 Uiso 1 1 calc GR . . . .
H18B H 0.6185 0.5811 0.3610 0.074 Uiso 1 1 calc GR . . . .
H18C H 0.6228 0.5490 0.4741 0.074 Uiso 1 1 calc GR . . . .
C19 C 0.8352(2) 0.4993(2) 0.4113(2) 0.0519(7) Uani 1 1 d . . . . .
H19A H 0.8533 0.5177 0.4813 0.078 Uiso 1 1 calc GR . . . .
H19B H 0.8361 0.5554 0.3693 0.078 Uiso 1 1 calc GR . . . .
H19C H 0.8977 0.4546 0.3960 0.078 Uiso 1 1 calc GR . . . .


_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 N7 1.222(3) . ?
O2 N7 1.277(3) . ?
O3 N7 1.199(3) . ?
N1 C1 1.345(3) . ?
N1 C5 1.340(3) . ?
N2 C6 1.349(3) . ?
N2 C10 1.334(3) . ?
N3 N4 1.358(3) . ?
N3 C11 1.330(3) . ?
N4 N5 1.298(3) . ?
N5 N6 1.362(3) . ?
N6 C11 1.324(3) . ?
C1 C2 1.388(3) . ?
C1 C6 1.492(3) . ?
C2 C3 1.395(3) . ?
C3 C4 1.395(3) . ?
C3 C12 1.531(3) . ?
C4 C5 1.386(3) . ?
C5 C11 1.472(3) . ?
C6 C7 1.373(3) . ?
C7 C8 1.401(3) . ?
C8 C9 1.394(3) . ?
C8 C16 1.531(3) . ?
C9 C10 1.370(4) . ?
C12 C13 1.545(4) . ?
C12 C14 1.529(4) . ?
C12 C15 1.520(4) . ?
C16 C17 1.534(4) . ?
C16 C18 1.535(4) . ?
C16 C19 1.535(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
C5 N1 C1 117.0(2) . . ?
C10 N2 C6 122.2(2) . . ?
C11 N3 N4 108.3(2) . . ?
N5 N4 N3 106.2(2) . . ?
N4 N5 N6 110.8(2) . . ?
C11 N6 N5 105.6(2) . . ?
O1 N7 O2 117.5(2) . . ?
O3 N7 O1 123.8(2) . . ?
O3 N7 O2 118.3(2) . . ?
N1 C1 C2 122.8(2) . . ?
N1 C1 C6 114.3(2) . . ?
C2 C1 C6 123.0(2) . . ?
C1 C2 C3 120.2(2) . . ?
C2 C3 C4 116.8(2) . . ?
C2 C3 C12 120.5(2) . . ?
C4 C3 C12 122.7(2) . . ?
C5 C4 C3 119.4(2) . . ?
N1 C5 C4 123.9(2) . . ?
N1 C5 C11 115.4(2) . . ?
C4 C5 C11 120.8(2) . . ?
N2 C6 C1 115.6(2) . . ?
N2 C6 C7 118.6(2) . . ?
C7 C6 C1 125.8(2) . . ?
C6 C7 C8 121.3(2) . . ?
C7 C8 C16 120.2(2) . . ?
C9 C8 C7 117.0(2) . . ?
C9 C8 C16 122.7(2) . . ?
C10 C9 C8 120.1(2) . . ?
N2 C10 C9 120.6(2) . . ?
N3 C11 C5 124.4(2) . . ?
N6 C11 N3 109.0(2) . . ?
N6 C11 C5 126.6(2) . . ?
C3 C12 C13 108.6(2) . . ?
C14 C12 C3 108.3(2) . . ?
C14 C12 C13 108.8(2) . . ?
C15 C12 C3 112.3(2) . . ?
C15 C12 C13 108.6(3) . . ?
C15 C12 C14 110.2(3) . . ?
C8 C16 C17 108.1(2) . . ?
C8 C16 C18 109.6(2) . . ?
C8 C16 C19 111.7(2) . . ?
C17 C16 C18 109.8(2) . . ?
C17 C16 C19 109.3(2) . . ?
C18 C16 C19 108.3(2) . . ?

_shelx_SHELXL_version_number     2014/7
_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_atw411sv-2
_database_code_depnum_ccdc_archive 'CCDC 1550720'
_audit_update_record             
;
2017-05-17 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;
_audit_creation_date             2017-03-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_shelx_SHELXL_version_number     2016/6

#==============================================================================

# start Validation Reply Form
_vrf_PLAT029_atw411sv-2          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.773 Note  
RESPONSE: Only domain 1 of a twin integrated dataset used for calculation, 
          therefore incomplete dataset.
;
_vrf_PLAT911_atw411sv-2          
;
PROBLEM: Missing # FCF Refl Between THmin & STh/L=  0.600       2085 Report
RESPONSE: Only domain 1 of a twin integrated dataset used for calculation, 
          therefore incomplete dataset.
;
_vrf_PLAT971_atw411sv-2          
;
PROBLEM: Check Calcd Residual Density  0.91A From      Sm       2.94 eA-3  
RESPONSE: Typical fourier trucation error, twinned crystal
;
_vrf_PLAT972_atw411sv-2          
;
PROBLEM: Check Calcd Residual Density  0.76A From      Sm      -2.84 eA-3  
RESPONSE: Typical fourier trucation error, twinned crystal
;
_vrf_PLAT973_atw411sv-2          
;
PROBLEM: Check Calcd Positive Residual Density on      Sm       1.62 eA-3  
RESPONSE: Typical fourier trucation error, twinned crystal
;
# end Validation Reply Form

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H25 N9 O10 Sm, C19 H25 N6, 2(C2 H3 N)'
_chemical_formula_sum            'C42 H56 N17 O10 Sm'
_chemical_formula_weight         1109.38
_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'
Sm Sm -0.1638 3.4418 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.7312(4)
_cell_length_b                   12.5933(4)
_cell_length_c                   18.8590(6)
_cell_angle_alpha                78.730(3)
_cell_angle_beta                 84.067(3)
_cell_angle_gamma                69.941(3)
_cell_volume                     2564.66(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    39418
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.04
_cell_measurement_theta_min      1.85
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.215
_exptl_absorpt_correction_T_min  0.1968
_exptl_absorpt_correction_T_max  0.8630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270.
Afterwards scaling of reflection intensities was performed within STOE LANA.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1138
_exptl_crystal_size_max          0.401
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.773
_diffrn_reflns_Laue_measured_fraction_max 0.668
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19286
_diffrn_reflns_point_group_measured_fraction_full 0.773
_diffrn_reflns_point_group_measured_fraction_max 0.668
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.864
_diffrn_reflns_theta_min         1.849
_diffrn_ambient_temperature      100
_diffrn_detector                 Pilatus100K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS 100K'
_diffrn_measured_fraction_theta_full 0.773
_diffrn_measured_fraction_theta_max 0.668
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Mo LFF Sealed Tube'
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_source_type              'Xenocs Genix3D microfocus'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9474
_reflns_number_total             10795
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.127.0 (STOE, 2016)
;
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
X-Area Integrate 1.71.0.0 (STOE, 2016)
X-Area X-Red 1.63.1.0 (STOE, 2016)
X-Area LANA 1.68.2.0 (STOE, 2016) 
PLATON (A.L.Spek, 2009)
;
_computing_structure_solution    'SHELXS-2016/6 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_molecular_graphics    'Diamond 4, Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  
;
MS Word, Olex2 (Dolomanov et al., 2009)
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.77, Darmstadt 2016
;
_refine_diff_density_max         2.806
_refine_diff_density_min         -2.452
_refine_diff_density_rms         0.158
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     646
_refine_ls_number_reflns         10795
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0642
_refine_ls_restrained_S_all      1.063
_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)+(0.1347P)²+2.5684P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1671
_refine_ls_wR_factor_ref         0.1841
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
C12 \\sim C13 \\sim C14 \\sim C15: within 1.7A with sigma of 0.004 and sigma
for terminal atoms of 0.008
3.a Rotating group:
 O10(H10A,H10B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C7(H7), C9(H9), C10(H10), N8(H8), N9(H9A), C21(H21), C23(H23),
  C26(H26), C28(H28), C29(H29)
3.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,
 H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C32(H32A,H32B,H32C), C33(H33A,
 H33B,H33C), C34(H34A,H34B,H34C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C),
 C38(H38A,H38B,H38C), C40(H40A,H40B,H40C), C42(H42A,H42B,H42C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Sm Sm 0.47258(2) 0.66408(2) 0.66635(2) 0.02449(10) Uani 1 1 d . . . . .
O1 O 0.6964(4) 0.6181(3) 0.63427(18) 0.0333(7) Uani 1 1 d . . . . .
O2 O 0.5932(4) 0.7938(3) 0.64375(19) 0.0367(8) Uani 1 1 d . . . . .
O3 O 0.7833(5) 0.7508(5) 0.6088(3) 0.0598(14) Uani 1 1 d . . . . .
O4 O 0.5108(3) 0.6981(3) 0.53082(17) 0.0306(7) Uani 1 1 d . . . . .
O5 O 0.3639(4) 0.6322(3) 0.56606(17) 0.0322(7) Uani 1 1 d . . . . .
O6 O 0.3938(4) 0.6902(4) 0.45074(18) 0.0388(9) Uani 1 1 d . . . . .
O7 O 0.3786(4) 0.5480(3) 0.76745(19) 0.0372(8) Uani 1 1 d . . . . .
O8 O 0.2487(4) 0.6887(4) 0.70284(19) 0.0340(8) Uani 1 1 d . . . . .
O9 O 0.1850(4) 0.5768(4) 0.7889(2) 0.0399(9) Uani 1 1 d . . . . .
O10 O 0.5647(3) 0.4644(3) 0.65097(18) 0.0315(7) Uani 1 1 d . . . . .
H10A H 0.539290 0.479190 0.606883 0.047 Uiso 1 1 d GR . . . .
H10B H 0.643679 0.428909 0.648903 0.047 Uiso 1 1 d GR . . . .
N1 N 0.3960(4) 0.8066(3) 0.75667(18) 0.0269(8) Uani 1 1 d . . . . .
N2 N 0.5869(4) 0.6170(4) 0.7844(2) 0.0296(8) Uani 1 1 d . . . . .
N3 N 0.3279(4) 0.8562(3) 0.61727(18) 0.0265(8) Uani 1 1 d . . . . .
N4 N 0.2694(4) 0.8992(4) 0.5547(2) 0.0317(9) Uani 1 1 d . . . . .
N5 N 0.1783(4) 0.9912(4) 0.56355(19) 0.0320(9) Uani 1 1 d . . . . .
N6 N 0.1741(4) 1.0123(4) 0.6314(2) 0.0303(9) Uani 1 1 d . . . . .
N13 N 0.6951(4) 0.7213(4) 0.6288(2) 0.0351(9) Uani 1 1 d . . . . .
N14 N 0.4221(4) 0.6734(4) 0.5141(2) 0.0304(9) Uani 1 1 d . . . . .
N15 N 0.2688(4) 0.6038(4) 0.7541(2) 0.0295(8) Uani 1 1 d . . . . .
C1 C 0.4397(5) 0.7841(4) 0.8233(2) 0.0277(9) Uani 1 1 d . . . . .
C2 C 0.3912(5) 0.8596(5) 0.8722(2) 0.0333(10) Uani 1 1 d . . . . .
H2 H 0.422776 0.840937 0.919141 0.040 Uiso 1 1 calc R . . . .
C3 C 0.2967(5) 0.9625(5) 0.8531(2) 0.0336(11) Uani 1 1 d . . . . .
C4 C 0.2534(5) 0.9860(4) 0.7840(2) 0.0282(9) Uani 1 1 d . . . . .
H4 H 0.189668 1.055071 0.768309 0.034 Uiso 1 1 calc R . . . .
C5 C 0.3055(5) 0.9059(4) 0.7378(2) 0.0264(9) Uani 1 1 d . . . . .
C6 C 0.5432(5) 0.6762(4) 0.8394(2) 0.0266(9) Uani 1 1 d . . . . .
C7 C 0.5973(5) 0.6383(4) 0.9069(2) 0.0304(9) Uani 1 1 d . . . . .
H7 H 0.565896 0.681659 0.944730 0.036 Uiso 1 1 calc R . . . .
C8 C 0.6964(5) 0.5376(4) 0.9190(2) 0.0297(9) Uani 1 1 d . . . . .
C9 C 0.7396(5) 0.4780(5) 0.8619(3) 0.0358(11) Uani 1 1 d . . . . .
H9 H 0.807050 0.409013 0.867432 0.043 Uiso 1 1 calc R . . . .
C10 C 0.6820(5) 0.5214(4) 0.7959(3) 0.0343(11) Uani 1 1 d . . . . .
H10 H 0.712622 0.480132 0.757047 0.041 Uiso 1 1 calc R . . . .
C11 C 0.2667(4) 0.9268(4) 0.6634(2) 0.0273(9) Uani 1 1 d . . . . .
C12 C 0.2428(7) 1.0459(6) 0.9067(3) 0.0517(15) Uani 1 1 d . U . . .
C13 C 0.1640(8) 0.9943(9) 0.9640(4) 0.071(2) Uani 1 1 d . U . . .
H13A H 0.094331 0.991154 0.940881 0.106 Uiso 1 1 calc GR . . . .
H13B H 0.134928 1.042255 1.001557 0.106 Uiso 1 1 calc GR . . . .
H13C H 0.212512 0.916575 0.985821 0.106 Uiso 1 1 calc GR . . . .
C14 C 0.1699(10) 1.1657(8) 0.8682(5) 0.083(3) Uani 1 1 d . U . . .
H14A H 0.221124 1.193228 0.829757 0.125 Uiso 1 1 calc GR . . . .
H14B H 0.143296 1.218567 0.903117 0.125 Uiso 1 1 calc GR . . . .
H14C H 0.098791 1.161992 0.847070 0.125 Uiso 1 1 calc GR . . . .
C15 C 0.3456(6) 1.0587(5) 0.9449(3) 0.0437(12) Uani 1 1 d . U . . .
H15A H 0.391317 0.984242 0.972473 0.065 Uiso 1 1 calc GR . . . .
H15B H 0.310996 1.114135 0.977801 0.065 Uiso 1 1 calc GR . . . .
H15C H 0.400059 1.085976 0.908691 0.065 Uiso 1 1 calc GR . . . .
C16 C 0.7511(5) 0.4932(5) 0.9942(2) 0.0347(10) Uani 1 1 d . . . . .
C17 C 0.7692(7) 0.5905(6) 1.0246(3) 0.0458(14) Uani 1 1 d . . . . .
H17A H 0.826853 0.620471 0.992934 0.069 Uiso 1 1 calc GR . . . .
H17B H 0.801046 0.561126 1.073223 0.069 Uiso 1 1 calc GR . . . .
H17C H 0.691162 0.652175 1.027102 0.069 Uiso 1 1 calc GR . . . .
C18 C 0.6588(6) 0.4484(6) 1.0445(3) 0.0422(13) Uani 1 1 d . . . . .
H18A H 0.581963 0.511461 1.047271 0.063 Uiso 1 1 calc GR . . . .
H18B H 0.690972 0.418088 1.092972 0.063 Uiso 1 1 calc GR . . . .
H18C H 0.644780 0.387370 1.025126 0.063 Uiso 1 1 calc GR . . . .
C19 C 0.8721(6) 0.3951(7) 0.9932(3) 0.0534(17) Uani 1 1 d . . . . .
H19A H 0.859057 0.329631 0.978656 0.080 Uiso 1 1 calc GR . . . .
H19B H 0.905172 0.371934 1.041558 0.080 Uiso 1 1 calc GR . . . .
H19C H 0.929492 0.420817 0.958576 0.080 Uiso 1 1 calc GR . . . .
N7 N 0.9475(4) 0.2282(4) 0.49975(19) 0.0263(7) Uani 1 1 d . . . . .
N8 N 1.0932(4) 0.0669(3) 0.42557(19) 0.0279(8) Uani 1 1 d . . . . .
H8 H 1.086100 0.058152 0.473084 0.033 Uiso 1 1 calc R . . . .
N9 N 0.9701(4) 0.1891(4) 0.65513(19) 0.0279(8) Uani 1 1 d . . . . .
H9A H 1.034721 0.140531 0.637076 0.033 Uiso 1 1 calc R . . . .
N10 N 0.9378(4) 0.1871(4) 0.7260(2) 0.0321(9) Uani 1 1 d . . . . .
N11 N 0.8380(4) 0.2718(4) 0.7302(2) 0.0320(9) Uani 1 1 d . . . . .
N12 N 0.8040(4) 0.3310(4) 0.6630(2) 0.0318(9) Uani 1 1 d . . . . .
C20 C 0.9567(4) 0.2598(4) 0.4277(2) 0.0272(9) Uani 1 1 d . . . . .
C21 C 0.9151(5) 0.3732(4) 0.3926(2) 0.0286(9) Uani 1 1 d . . . . .
H21 H 0.924385 0.390446 0.341425 0.034 Uiso 1 1 calc R . . . .
C22 C 0.8600(4) 0.4617(4) 0.4319(2) 0.0273(9) Uani 1 1 d . . . . .
C23 C 0.8465(4) 0.4291(4) 0.5070(2) 0.0276(9) Uani 1 1 d . . . . .
H23 H 0.807203 0.485276 0.536608 0.033 Uiso 1 1 calc R . . . .
C24 C 0.8917(4) 0.3131(4) 0.5376(2) 0.0258(8) Uani 1 1 d . . . . .
C25 C 1.0258(4) 0.1675(4) 0.3867(2) 0.0265(9) Uani 1 1 d . . . . .
C26 C 1.0346(5) 0.1778(4) 0.3118(2) 0.0280(9) Uani 1 1 d . . . . .
H26 H 0.984069 0.245144 0.283287 0.034 Uiso 1 1 calc R . . . .
C27 C 1.1161(5) 0.0914(4) 0.2774(2) 0.0294(9) Uani 1 1 d . . . . .
C28 C 1.1841(5) -0.0099(4) 0.3210(2) 0.0303(10) Uani 1 1 d . . . . .
H28 H 1.239352 -0.071014 0.299457 0.036 Uiso 1 1 calc R . . . .
C29 C 1.1702(5) -0.0201(4) 0.3953(2) 0.0293(9) Uani 1 1 d . . . . .
H29 H 1.215317 -0.088867 0.425060 0.035 Uiso 1 1 calc R . . . .
C30 C 0.8872(5) 0.2776(4) 0.6169(2) 0.0276(9) Uani 1 1 d . . . . .
C31 C 0.8163(5) 0.5866(4) 0.3936(2) 0.0265(8) Uani 1 1 d . . . . .
C32 C 0.6890(5) 0.6123(5) 0.3656(3) 0.0363(11) Uani 1 1 d . . . . .
H32A H 0.693528 0.559964 0.332421 0.054 Uiso 1 1 calc GR . . . .
H32B H 0.659563 0.691713 0.340104 0.054 Uiso 1 1 calc GR . . . .
H32C H 0.633120 0.601613 0.406597 0.054 Uiso 1 1 calc GR . . . .
C33 C 0.9030(6) 0.6058(5) 0.3293(3) 0.0398(12) Uani 1 1 d . . . . .
H33A H 0.985250 0.584266 0.346418 0.060 Uiso 1 1 calc GR . . . .
H33B H 0.875796 0.686862 0.306724 0.060 Uiso 1 1 calc GR . . . .
H33C H 0.903094 0.558452 0.293730 0.060 Uiso 1 1 calc GR . . . .
C34 C 0.8068(5) 0.6690(4) 0.4456(3) 0.0324(10) Uani 1 1 d . . . . .
H34A H 0.741293 0.666559 0.481919 0.049 Uiso 1 1 calc GR . . . .
H34B H 0.789130 0.747221 0.418319 0.049 Uiso 1 1 calc GR . . . .
H34C H 0.883751 0.646135 0.469654 0.049 Uiso 1 1 calc GR . . . .
C35 C 1.1305(5) 0.1112(4) 0.1950(2) 0.0340(11) Uani 1 1 d . . . . .
C36 C 1.0087(6) 0.1294(7) 0.1640(3) 0.0497(16) Uani 1 1 d . . . . .
H36A H 0.985277 0.060729 0.180457 0.075 Uiso 1 1 calc GR . . . .
H36B H 1.015890 0.143764 0.111054 0.075 Uiso 1 1 calc GR . . . .
H36C H 0.946674 0.195496 0.180720 0.075 Uiso 1 1 calc GR . . . .
C37 C 1.1665(9) 0.2201(7) 0.1704(3) 0.0564(19) Uani 1 1 d . . . . .
H37A H 1.104786 0.285082 0.188425 0.085 Uiso 1 1 calc GR . . . .
H37B H 1.172237 0.236578 0.117428 0.085 Uiso 1 1 calc GR . . . .
H37C H 1.245232 0.207839 0.189762 0.085 Uiso 1 1 calc GR . . . .
C38 C 1.2276(6) 0.0101(5) 0.1673(3) 0.0451(14) Uani 1 1 d . . . . .
H38A H 1.305108 -0.003885 0.188706 0.068 Uiso 1 1 calc GR . . . .
H38B H 1.236523 0.027903 0.114460 0.068 Uiso 1 1 calc GR . . . .
H38C H 1.203291 -0.058484 0.180858 0.068 Uiso 1 1 calc GR . . . .
N16 N 0.4975(7) 1.0726(6) 0.7177(4) 0.0585(15) Uani 1 1 d . . . . .
C39 C 0.4988(6) 1.0666(6) 0.6588(4) 0.0455(14) Uani 1 1 d . . . . .
C40 C 0.4982(7) 1.0600(6) 0.5819(3) 0.0488(15) Uani 1 1 d . . . . .
H40A H 0.521664 1.122768 0.552112 0.073 Uiso 1 1 calc GR . . . .
H40B H 0.416486 1.066398 0.569891 0.073 Uiso 1 1 calc GR . . . .
H40C H 0.555940 0.986330 0.572353 0.073 Uiso 1 1 calc GR . . . .
N17 N 0.5649(8) 0.2363(6) 0.9446(3) 0.0674(19) Uani 1 1 d . . . . .
C41 C 0.5528(6) 0.2532(5) 0.8844(3) 0.0425(13) Uani 1 1 d . . . . .
C42 C 0.5365(8) 0.2758(6) 0.8072(3) 0.0526(17) Uani 1 1 d . . . . .
H42A H 0.615277 0.266476 0.781440 0.079 Uiso 1 1 calc GR . . . .
H42B H 0.481816 0.354490 0.793027 0.079 Uiso 1 1 calc GR . . . .
H42C H 0.501222 0.221821 0.795005 0.079 Uiso 1 1 calc GR . . . .


_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
Sm O1 2.523(4) . ?
Sm O2 2.458(4) . ?
Sm O4 2.527(3) . ?
Sm O5 2.551(4) . ?
Sm O7 2.563(3) . ?
Sm O8 2.572(4) . ?
Sm O10 2.435(3) . ?
Sm N1 2.589(4) . ?
Sm N2 2.581(4) . ?
Sm N3 2.495(4) . ?
Sm N13 2.923(5) . ?
Sm N14 2.964(4) . ?
O1 N13 1.278(6) . ?
O2 N13 1.275(6) . ?
O3 N13 1.217(7) . ?
O4 N14 1.268(6) . ?
O5 N14 1.266(6) . ?
O6 N14 1.231(5) . ?
O7 N15 1.262(6) . ?
O8 N15 1.266(5) . ?
O9 N15 1.234(5) . ?
O10 H10A 0.8761 . ?
O10 H10B 0.8805 . ?
N1 C1 1.347(6) . ?
N1 C5 1.346(6) . ?
N2 C6 1.351(6) . ?
N2 C10 1.329(6) . ?
N3 N4 1.348(5) . ?
N3 C11 1.342(5) . ?
N4 N5 1.304(6) . ?
N5 N6 1.350(5) . ?
N6 C11 1.335(6) . ?
C1 C2 1.394(6) . ?
C1 C6 1.482(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.397(7) . ?
C3 C4 1.388(6) . ?
C3 C12 1.534(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.399(6) . ?
C5 C11 1.466(6) . ?
C6 C7 1.404(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.393(7) . ?
C8 C9 1.387(7) . ?
C8 C16 1.539(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.399(7) . ?
C10 H10 0.9500 . ?
C12 C13 1.541(12) . ?
C12 C14 1.533(11) . ?
C12 C15 1.535(9) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.534(9) . ?
C16 C18 1.545(8) . ?
C16 C19 1.530(8) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
N7 C20 1.343(5) . ?
N7 C24 1.342(6) . ?
N8 H8 0.8800 . ?
N8 C25 1.355(6) . ?
N8 C29 1.342(6) . ?
N9 H9A 0.8800 . ?
N9 N10 1.349(5) . ?
N9 C30 1.340(6) . ?
N10 N11 1.292(6) . ?
N11 N12 1.361(6) . ?
N12 C30 1.328(6) . ?
C20 C21 1.392(6) . ?
C20 C25 1.477(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.393(6) . ?
C22 C23 1.403(6) . ?
C22 C31 1.528(6) . ?
C23 H23 0.9500 . ?
C23 C24 1.397(7) . ?
C24 C30 1.476(6) . ?
C25 C26 1.389(6) . ?
C26 H26 0.9500 . ?
C26 C27 1.397(7) . ?
C27 C28 1.402(7) . ?
C27 C35 1.527(6) . ?
C28 H28 0.9500 . ?
C28 C29 1.380(6) . ?
C29 H29 0.9500 . ?
C31 C32 1.542(7) . ?
C31 C33 1.537(7) . ?
C31 C34 1.532(7) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C36 1.527(9) . ?
C35 C37 1.543(9) . ?
C35 C38 1.527(7) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
N16 C39 1.127(9) . ?
C39 C40 1.469(10) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
N17 C41 1.128(8) . ?
C41 C42 1.447(8) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 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
O1 Sm O4 68.94(12) . . ?
O1 Sm O5 110.49(12) . . ?
O1 Sm O7 125.52(12) . . ?
O1 Sm O8 174.14(12) . . ?
O1 Sm N1 112.71(13) . . ?
O1 Sm N2 71.58(12) . . ?
O1 Sm N13 25.84(13) . . ?
O1 Sm N14 90.71(12) . . ?
O2 Sm O1 51.40(13) . . ?
O2 Sm O4 74.71(12) . . ?
O2 Sm O5 122.32(12) . . ?
O2 Sm O7 142.99(13) . . ?
O2 Sm O8 134.26(13) . . ?
O2 Sm N1 71.82(13) . . ?
O2 Sm N2 76.60(13) . . ?
O2 Sm N3 74.76(14) . . ?
O2 Sm N13 25.58(13) . . ?
O2 Sm N14 98.02(13) . . ?
O4 Sm O5 50.14(12) . . ?
O4 Sm O7 142.11(13) . . ?
O4 Sm O8 112.76(12) . . ?
O4 Sm N1 130.88(12) . . ?
O4 Sm N2 140.11(13) . . ?
O4 Sm N13 69.05(12) . . ?
O4 Sm N14 25.12(12) . . ?
O5 Sm O7 94.10(13) . . ?
O5 Sm O8 68.53(12) . . ?
O5 Sm N1 130.64(13) . . ?
O5 Sm N2 158.30(13) . . ?
O5 Sm N13 118.71(12) . . ?
O5 Sm N14 25.15(12) . . ?
O7 Sm O8 49.56(12) . . ?
O7 Sm N1 79.61(13) . . ?
O7 Sm N2 69.31(14) . . ?
O7 Sm N13 140.69(13) . . ?
O7 Sm N14 118.87(14) . . ?
O8 Sm N1 70.75(13) . . ?
O8 Sm N2 107.09(13) . . ?
O8 Sm N13 159.83(14) . . ?
O8 Sm N14 89.82(12) . . ?
O10 Sm O1 69.28(13) . . ?
O10 Sm O2 120.57(13) . . ?
O10 Sm O4 82.03(11) . . ?
O10 Sm O5 72.10(12) . . ?
O10 Sm O7 73.88(12) . . ?
O10 Sm O8 105.15(13) . . ?
O10 Sm N1 146.53(11) . . ?
O10 Sm N2 89.39(12) . . ?
O10 Sm N3 145.78(12) . . ?
O10 Sm N13 95.01(13) . . ?
O10 Sm N14 77.58(11) . . ?
N1 Sm N13 92.69(13) . . ?
N1 Sm N14 134.26(12) . . ?
N2 Sm N1 61.95(13) . . ?
N2 Sm N13 73.06(13) . . ?
N2 Sm N14 160.99(13) . . ?
N3 Sm O1 119.60(13) . . ?
N3 Sm O4 72.62(11) . . ?
N3 Sm O5 74.02(13) . . ?
N3 Sm O7 113.58(13) . . ?
N3 Sm O8 65.99(13) . . ?
N3 Sm N1 64.62(12) . . ?
N3 Sm N2 124.78(13) . . ?
N3 Sm N13 96.90(14) . . ?
N3 Sm N14 69.66(11) . . ?
N13 Sm N14 94.12(13) . . ?
N13 O1 Sm 94.9(3) . . ?
N13 O2 Sm 98.0(3) . . ?
N14 O4 Sm 97.1(2) . . ?
N14 O5 Sm 96.0(3) . . ?
N15 O7 Sm 97.1(3) . . ?
N15 O8 Sm 96.6(3) . . ?
Sm O10 H10A 92.4 . . ?
Sm O10 H10B 123.5 . . ?
H10A O10 H10B 107.3 . . ?
C1 N1 Sm 122.9(3) . . ?
C5 N1 Sm 119.1(3) . . ?
C5 N1 C1 118.0(4) . . ?
C6 N2 Sm 122.2(3) . . ?
C10 N2 Sm 118.7(3) . . ?
C10 N2 C6 118.3(4) . . ?
N4 N3 Sm 133.1(3) . . ?
C11 N3 Sm 118.9(3) . . ?
C11 N3 N4 105.5(4) . . ?
N5 N4 N3 108.7(4) . . ?
N4 N5 N6 110.4(4) . . ?
C11 N6 N5 104.6(4) . . ?
O1 N13 Sm 59.3(3) . . ?
O2 N13 Sm 56.4(3) . . ?
O2 N13 O1 115.6(5) . . ?
O3 N13 Sm 175.1(4) . . ?
O3 N13 O1 123.2(5) . . ?
O3 N13 O2 121.2(5) . . ?
O4 N14 Sm 57.8(2) . . ?
O5 N14 Sm 58.9(2) . . ?
O5 N14 O4 116.2(4) . . ?
O6 N14 Sm 172.8(3) . . ?
O6 N14 O4 121.5(4) . . ?
O6 N14 O5 122.2(5) . . ?
O7 N15 Sm 58.2(2) . . ?
O7 N15 O8 116.7(4) . . ?
O8 N15 Sm 58.6(2) . . ?
O9 N15 Sm 178.2(3) . . ?
O9 N15 O7 121.8(4) . . ?
O9 N15 O8 121.5(4) . . ?
N1 C1 C2 121.4(4) . . ?
N1 C1 C6 115.4(4) . . ?
C2 C1 C6 123.2(4) . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.8(4) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 C12 121.0(4) . . ?
C4 C3 C2 117.5(4) . . ?
C4 C3 C12 121.5(5) . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.7(4) . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 123.5(4) . . ?
N1 C5 C11 114.8(4) . . ?
C4 C5 C11 121.6(4) . . ?
N2 C6 C1 116.3(4) . . ?
N2 C6 C7 120.9(4) . . ?
C7 C6 C1 122.7(4) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.7(4) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C16 120.4(4) . . ?
C9 C8 C7 117.5(4) . . ?
C9 C8 C16 122.1(4) . . ?
C8 C9 H9 120.6 . . ?
C8 C9 C10 118.8(5) . . ?
C10 C9 H9 120.6 . . ?
N2 C10 C9 123.8(5) . . ?
N2 C10 H10 118.1 . . ?
C9 C10 H10 118.1 . . ?
N3 C11 C5 120.6(4) . . ?
N6 C11 N3 111.0(4) . . ?
N6 C11 C5 128.5(4) . . ?
C3 C12 C13 107.9(6) . . ?
C3 C12 C15 109.7(5) . . ?
C14 C12 C3 111.5(5) . . ?
C14 C12 C13 111.8(7) . . ?
C14 C12 C15 107.3(7) . . ?
C15 C12 C13 108.6(5) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C16 C18 106.9(4) . . ?
C17 C16 C8 110.8(4) . . ?
C17 C16 C18 108.5(5) . . ?
C19 C16 C8 112.4(4) . . ?
C19 C16 C17 109.4(5) . . ?
C19 C16 C18 108.8(5) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C24 N7 C20 116.1(4) . . ?
C25 N8 H8 118.3 . . ?
C29 N8 H8 118.3 . . ?
C29 N8 C25 123.3(4) . . ?
N10 N9 H9A 125.8 . . ?
C30 N9 H9A 125.8 . . ?
C30 N9 N10 108.4(4) . . ?
N11 N10 N9 106.9(4) . . ?
N10 N11 N12 110.4(4) . . ?
C30 N12 N11 106.1(4) . . ?
N7 C20 C21 123.5(4) . . ?
N7 C20 C25 116.0(4) . . ?
C21 C20 C25 120.2(4) . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.5(4) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C23 116.3(4) . . ?
C21 C22 C31 120.6(4) . . ?
C23 C22 C31 123.1(4) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 C22 119.2(4) . . ?
C24 C23 H23 120.4 . . ?
N7 C24 C23 124.4(4) . . ?
N7 C24 C30 115.4(4) . . ?
C23 C24 C30 120.1(4) . . ?
N8 C25 C20 116.8(4) . . ?
N8 C25 C26 117.4(4) . . ?
C26 C25 C20 125.6(4) . . ?
C25 C26 H26 119.3 . . ?
C25 C26 C27 121.5(4) . . ?
C27 C26 H26 119.3 . . ?
C26 C27 C28 117.9(4) . . ?
C26 C27 C35 119.5(4) . . ?
C28 C27 C35 122.5(4) . . ?
C27 C28 H28 120.3 . . ?
C29 C28 C27 119.5(4) . . ?
C29 C28 H28 120.3 . . ?
N8 C29 C28 120.2(4) . . ?
N8 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
N9 C30 C24 125.7(4) . . ?
N12 C30 N9 108.2(4) . . ?
N12 C30 C24 126.0(4) . . ?
C22 C31 C32 107.9(4) . . ?
C22 C31 C33 110.5(4) . . ?
C22 C31 C34 111.3(4) . . ?
C33 C31 C32 109.2(4) . . ?
C34 C31 C32 108.4(4) . . ?
C34 C31 C33 109.4(4) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C27 C35 C37 108.1(4) . . ?
C36 C35 C27 108.4(4) . . ?
C36 C35 C37 109.6(6) . . ?
C38 C35 C27 112.2(4) . . ?
C38 C35 C36 109.3(5) . . ?
C38 C35 C37 109.2(5) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N16 C39 C40 178.9(8) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
N17 C41 C42 179.5(8) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Sm O1 N13 O2 2.9(4) . . . . ?
Sm O1 N13 O3 -175.0(5) . . . . ?
Sm O2 N13 O1 -3.0(4) . . . . ?
Sm O2 N13 O3 175.0(5) . . . . ?
Sm O4 N14 O5 -7.6(4) . . . . ?
Sm O4 N14 O6 171.5(4) . . . . ?
Sm O5 N14 O4 7.5(4) . . . . ?
Sm O5 N14 O6 -171.6(4) . . . . ?
Sm O7 N15 O8 -1.8(5) . . . . ?
Sm O7 N15 O9 177.8(4) . . . . ?
Sm O8 N15 O7 1.8(4) . . . . ?
Sm O8 N15 O9 -177.8(4) . . . . ?
Sm N1 C1 C2 -176.0(4) . . . . ?
Sm N1 C1 C6 5.4(6) . . . . ?
Sm N1 C5 C4 176.7(4) . . . . ?
Sm N1 C5 C11 -5.2(6) . . . . ?
Sm N2 C6 C1 -12.1(6) . . . . ?
Sm N2 C6 C7 170.3(4) . . . . ?
Sm N2 C10 C9 -170.0(4) . . . . ?
Sm N3 N4 N5 161.4(4) . . . . ?
Sm N3 C11 N6 -165.3(3) . . . . ?
Sm N3 C11 C5 15.8(6) . . . . ?
N1 C1 C2 C3 -1.1(8) . . . . ?
N1 C1 C6 N2 4.2(7) . . . . ?
N1 C1 C6 C7 -178.1(5) . . . . ?
N1 C5 C11 N3 -6.8(7) . . . . ?
N1 C5 C11 N6 174.4(5) . . . . ?
N2 C6 C7 C8 -0.9(8) . . . . ?
N3 N4 N5 N6 0.4(6) . . . . ?
N4 N3 C11 N6 -1.0(6) . . . . ?
N4 N3 C11 C5 -179.9(4) . . . . ?
N4 N5 N6 C11 -1.0(6) . . . . ?
N5 N6 C11 N3 1.2(6) . . . . ?
N5 N6 C11 C5 -179.9(5) . . . . ?
C1 N1 C5 C4 -0.9(7) . . . . ?
C1 N1 C5 C11 177.2(4) . . . . ?
C1 C2 C3 C4 0.1(8) . . . . ?
C1 C2 C3 C12 179.9(6) . . . . ?
C1 C6 C7 C8 -178.4(5) . . . . ?
C2 C1 C6 N2 -174.4(5) . . . . ?
C2 C1 C6 C7 3.3(8) . . . . ?
C2 C3 C4 C5 0.5(8) . . . . ?
C2 C3 C12 C13 -74.1(8) . . . . ?
C2 C3 C12 C14 162.8(7) . . . . ?
C2 C3 C12 C15 44.1(8) . . . . ?
C3 C4 C5 N1 -0.1(8) . . . . ?
C3 C4 C5 C11 -178.1(5) . . . . ?
C4 C3 C12 C13 105.7(7) . . . . ?
C4 C3 C12 C14 -17.4(10) . . . . ?
C4 C3 C12 C15 -136.1(6) . . . . ?
C4 C5 C11 N3 171.4(5) . . . . ?
C4 C5 C11 N6 -7.4(8) . . . . ?
C5 N1 C1 C2 1.5(7) . . . . ?
C5 N1 C1 C6 -177.1(4) . . . . ?
C6 N2 C10 C9 0.2(9) . . . . ?
C6 C1 C2 C3 177.4(5) . . . . ?
C6 C7 C8 C9 0.7(8) . . . . ?
C6 C7 C8 C16 -176.8(5) . . . . ?
C7 C8 C9 C10 -0.1(8) . . . . ?
C7 C8 C16 C17 -46.9(7) . . . . ?
C7 C8 C16 C18 71.2(6) . . . . ?
C7 C8 C16 C19 -169.5(6) . . . . ?
C8 C9 C10 N2 -0.4(9) . . . . ?
C9 C8 C16 C17 135.7(6) . . . . ?
C9 C8 C16 C18 -106.2(6) . . . . ?
C9 C8 C16 C19 13.1(8) . . . . ?
C10 N2 C6 C1 178.1(5) . . . . ?
C10 N2 C6 C7 0.4(8) . . . . ?
C11 N3 N4 N5 0.3(6) . . . . ?
C12 C3 C4 C5 -179.3(6) . . . . ?
C16 C8 C9 C10 177.4(5) . . . . ?
N7 C20 C21 C22 -0.3(8) . . . . ?
N7 C20 C25 N8 -13.1(7) . . . . ?
N7 C20 C25 C26 172.0(5) . . . . ?
N7 C24 C30 N9 30.3(7) . . . . ?
N7 C24 C30 N12 -153.4(5) . . . . ?
N8 C25 C26 C27 -4.5(7) . . . . ?
N9 N10 N11 N12 -0.7(6) . . . . ?
N10 N9 C30 N12 0.3(6) . . . . ?
N10 N9 C30 C24 177.1(5) . . . . ?
N10 N11 N12 C30 0.8(6) . . . . ?
N11 N12 C30 N9 -0.7(6) . . . . ?
N11 N12 C30 C24 -177.5(5) . . . . ?
C20 N7 C24 C23 -1.5(7) . . . . ?
C20 N7 C24 C30 -177.4(4) . . . . ?
C20 C21 C22 C23 -1.8(7) . . . . ?
C20 C21 C22 C31 178.9(5) . . . . ?
C20 C25 C26 C27 170.4(5) . . . . ?
C21 C20 C25 N8 161.0(5) . . . . ?
C21 C20 C25 C26 -13.9(8) . . . . ?
C21 C22 C23 C24 2.1(7) . . . . ?
C21 C22 C31 C32 83.8(6) . . . . ?
C21 C22 C31 C33 -35.6(7) . . . . ?
C21 C22 C31 C34 -157.3(5) . . . . ?
C22 C23 C24 N7 -0.6(8) . . . . ?
C22 C23 C24 C30 175.2(4) . . . . ?
C23 C22 C31 C32 -95.5(5) . . . . ?
C23 C22 C31 C33 145.1(5) . . . . ?
C23 C22 C31 C34 23.4(7) . . . . ?
C23 C24 C30 N9 -145.8(5) . . . . ?
C23 C24 C30 N12 30.5(8) . . . . ?
C24 N7 C20 C21 1.9(7) . . . . ?
C24 N7 C20 C25 175.8(4) . . . . ?
C25 N8 C29 C28 0.1(8) . . . . ?
C25 C20 C21 C22 -173.9(5) . . . . ?
C25 C26 C27 C28 3.9(7) . . . . ?
C25 C26 C27 C35 -174.6(5) . . . . ?
C26 C27 C28 C29 -1.2(8) . . . . ?
C26 C27 C35 C36 -61.9(6) . . . . ?
C26 C27 C35 C37 56.8(7) . . . . ?
C26 C27 C35 C38 177.3(5) . . . . ?
C27 C28 C29 N8 -0.8(8) . . . . ?
C28 C27 C35 C36 119.7(6) . . . . ?
C28 C27 C35 C37 -121.6(6) . . . . ?
C28 C27 C35 C38 -1.1(8) . . . . ?
C29 N8 C25 C20 -172.8(5) . . . . ?
C29 N8 C25 C26 2.5(7) . . . . ?
C30 N9 N10 N11 0.2(6) . . . . ?
C31 C22 C23 C24 -178.6(5) . . . . ?
C35 C27 C28 C29 177.3(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
