# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_150907_ipr_btp_pd
_database_code_depnum_ccdc_archive 'CCDC 1429206'
_audit_update_record             
;
2015-10-02 deposited with the CCDC.	2019-05-07 downloaded from the CCDC.
;
_audit_creation_date             2015-09-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        'iPr-BTP-Pd complex'
_chemical_formula_moiety         'C23 H31 N8 O3 Pd, N O3'
_chemical_formula_sum            'C23 H31 N9 O6 Pd'
_chemical_formula_weight         635.97
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 Pd1'
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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   23.0533(11)
_cell_length_b                   8.7675(4)
_cell_length_c                   31.1560(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.251(4)
_cell_angle_gamma                90.00
_cell_volume                     6287.1(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7817
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5505
_cell_measurement_theta_min      2.9654
_exptl_absorpt_coefficient_mu    0.638
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79020
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2608
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            35722
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.97
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0300219000
_diffrn_orient_matrix_UB_12      0.0119939000
_diffrn_orient_matrix_UB_13      0.0026084000
_diffrn_orient_matrix_UB_21      -0.0068017000
_diffrn_orient_matrix_UB_22      -0.0398013000
_diffrn_orient_matrix_UB_23      -0.0194514000
_diffrn_orient_matrix_UB_31      -0.0012794000
_diffrn_orient_matrix_UB_32      -0.0694743000
_diffrn_orient_matrix_UB_33      0.0115875000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                6504
_reflns_number_total             11420
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     719
_refine_ls_number_reflns         11420
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0677
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0510P)²+11.3703P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1511
_refine_ls_wR_factor_ref         0.1696
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C15(H15), C18(H18), C21(H21), C35(H35), C38(H38), C41(H41), C44(H44)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C28(H28), C29(H29), C30(H30)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C23(H23A,
 H23B,H23C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C39(H39A,H39B,H39C),
 C40(H40A,H40B,H40C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C), C45(H45A,H45B,
 H45C), C46(H46A,H46B,H46C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Pd1 Pd 0.120043(19) 0.85808(5) 0.270663(14) 0.05016(15) Uani 1 d . . .
O1 O 0.1082(2) 0.6378(4) 0.28531(15) 0.0673(12) Uani 1 d . . .
O2 O 0.0474(3) 0.4622(6) 0.2979(2) 0.119(2) Uani 1 d . . .
O3 O 0.0175(3) 0.6906(7) 0.2860(2) 0.115(2) Uani 1 d . . .
N1 N 0.0587(2) 0.7478(5) 0.18777(17) 0.0594(13) Uani 1 d . . .
N2 N 0.0863(2) 0.8610(5) 0.21002(14) 0.0531(12) Uani 1 d . . .
N3 N 0.0746(2) 1.0262(5) 0.14989(17) 0.0576(12) Uani 1 d . . .
N4 N 0.1378(2) 1.0647(5) 0.25432(15) 0.0530(11) Uani 1 d . . .
N5 N 0.1619(2) 0.9276(5) 0.32539(17) 0.0645(14) Uani 1 d . . .
N6 N 0.1712(2) 0.8456(5) 0.36190(17) 0.0612(13) Uani 1 d . . .
N7 N 0.2113(2) 1.1399(5) 0.35752(16) 0.0610(13) Uani 1 d . . .
N15 N 0.0559(3) 0.5949(7) 0.2908(2) 0.0785(16) Uani 1 d . . .
C1 C 0.0404(3) 0.7705(6) 0.14767(18) 0.0542(14) Uani 1 d . . .
C2 C 0.0492(3) 0.9130(7) 0.12762(19) 0.0567(15) Uani 1 d . . .
C3 C 0.0915(3) 0.9937(7) 0.19028(19) 0.0638(17) Uani 1 d . . .
C4 C 0.1220(2) 1.1149(6) 0.21665(16) 0.0459(13) Uani 1 d . . .
C5 C 0.1352(3) 1.2637(7) 0.2049(2) 0.0641(16) Uani 1 d . . .
H5 H 0.1239 1.3009 0.1778 0.077 Uiso 1 calc . . R
C6 C 0.1652(3) 1.3538(7) 0.2343(2) 0.0711(19) Uani 1 d . . .
H6 H 0.1750 1.4528 0.2268 0.085 Uiso 1 calc . . R
C7 C 0.1811(3) 1.3004(7) 0.27498(19) 0.0602(15) Uani 1 d . . .
H7 H 0.1998 1.3634 0.2954 0.072 Uiso 1 calc . . R
C8 C 0.1687(3) 1.1521(6) 0.28420(19) 0.0543(14) Uani 1 d . . .
C9 C 0.1820(2) 1.0703(7) 0.32542(16) 0.0505(13) Uani 1 d . . .
C10 C 0.2209(3) 1.0601(7) 0.39338(19) 0.0650(16) Uani 1 d . . .
C11 C 0.1985(3) 0.9106(7) 0.3950(2) 0.0657(17) Uani 1 d . . .
C12 C 0.0088(3) 0.6373(7) 0.1270(2) 0.078(2) Uani 1 d . . .
H12 H 0.0094 0.6610 0.0963 0.093 Uiso 1 calc . . R
C13 C 0.0455(9) 0.5034(13) 0.1313(7) 0.328(16) Uani 1 d . . .
H13A H 0.0507 0.4609 0.1034 0.492 Uiso 1 calc . . GR
H13B H 0.0276 0.4291 0.1489 0.492 Uiso 1 calc . . GR
H13C H 0.0827 0.5314 0.1445 0.492 Uiso 1 calc . . GR
C14 C -0.0561(6) 0.6538(19) 0.1359(6) 0.250(11) Uani 1 d . . .
H14A H -0.0651 0.7595 0.1399 0.375 Uiso 1 calc . . GR
H14B H -0.0641 0.5978 0.1614 0.375 Uiso 1 calc . . GR
H14C H -0.0794 0.6142 0.1119 0.375 Uiso 1 calc . . GR
C15 C 0.0286(3) 0.9441(8) 0.0809(2) 0.0725(19) Uani 1 d . . .
H15 H -0.0005 0.8683 0.0713 0.087 Uiso 1 calc . . R
C16 C 0.0776(5) 0.936(2) 0.0545(3) 0.191(6) Uani 1 d . . .
H16A H 0.1090 0.9953 0.0674 0.287 Uiso 1 calc . . GR
H16B H 0.0668 0.9763 0.0264 0.287 Uiso 1 calc . . GR
H16C H 0.0896 0.8320 0.0519 0.287 Uiso 1 calc . . GR
C17 C 0.0038(7) 1.1005(16) 0.0760(4) 0.209(8) Uani 1 d . . .
H17A H -0.0288 1.1104 0.0937 0.313 Uiso 1 calc . . GR
H17B H -0.0086 1.1177 0.0465 0.313 Uiso 1 calc . . GR
H17C H 0.0329 1.1743 0.0848 0.313 Uiso 1 calc . . GR
C18 C 0.2543(4) 1.1446(10) 0.4288(2) 0.101(3) Uani 1 d . . .
H18 H 0.2588 1.0789 0.4542 0.121 Uiso 1 calc . . R
C19 C 0.3132(6) 1.186(2) 0.4143(4) 0.238(9) Uani 1 d . . .
H19A H 0.3354 1.0944 0.4107 0.357 Uiso 1 calc . . GR
H19B H 0.3328 1.2496 0.4355 0.357 Uiso 1 calc . . GR
H19C H 0.3090 1.2393 0.3874 0.357 Uiso 1 calc . . GR
C20 C 0.2213(7) 1.2875(13) 0.4401(4) 0.198(7) Uani 1 d . . .
H20A H 0.2166 1.3520 0.4153 0.297 Uiso 1 calc . . GR
H20B H 0.2426 1.3411 0.4628 0.297 Uiso 1 calc . . GR
H20C H 0.1838 1.2596 0.4495 0.297 Uiso 1 calc . . GR
C21 C 0.2084(4) 0.8123(9) 0.4351(2) 0.088(2) Uani 1 d . . .
H21 H 0.2070 0.8793 0.4602 0.105 Uiso 1 calc . . R
C22 C 0.2683(5) 0.7419(11) 0.4358(3) 0.133(4) Uani 1 d . . .
H22A H 0.2678 0.6562 0.4166 0.199 Uiso 1 calc . . GR
H22B H 0.2794 0.7084 0.4644 0.199 Uiso 1 calc . . GR
H22C H 0.2956 0.8162 0.4268 0.199 Uiso 1 calc . . GR
C23 C 0.1601(5) 0.6949(11) 0.4377(3) 0.135(4) Uani 1 d . . .
H23A H 0.1231 0.7443 0.4331 0.202 Uiso 1 calc . . GR
H23B H 0.1625 0.6479 0.4656 0.202 Uiso 1 calc . . GR
H23C H 0.1643 0.6185 0.4160 0.202 Uiso 1 calc . . GR
Pd2 Pd 0.380121(19) 0.63424(5) 0.229342(14) 0.04977(15) Uani 1 d . . .
O4 O 0.3919(2) 0.8546(4) 0.21347(14) 0.0645(11) Uani 1 d . . .
O5 O 0.4532(3) 1.0308(6) 0.2017(2) 0.129(2) Uani 1 d . . .
O6 O 0.4833(3) 0.8014(7) 0.2144(2) 0.117(2) Uani 1 d . . .
N8 N 0.3293(2) 0.6465(5) 0.13761(15) 0.0559(12) Uani 1 d . . .
N9 N 0.33770(18) 0.5661(5) 0.17331(13) 0.0480(11) Uani 1 d . . .
N10 N 0.2894(3) 0.3506(6) 0.14372(17) 0.0700(15) Uani 1 d . . .
N11 N 0.36175(19) 0.4261(5) 0.24407(15) 0.0502(11) Uani 1 d . . .
N12 N 0.41491(18) 0.6283(5) 0.29124(15) 0.0510(11) Uani 1 d . . .
N13 N 0.4396(2) 0.7460(5) 0.31131(15) 0.0568(12) Uani 1 d . . .
N14 N 0.4261(2) 0.4662(6) 0.35114(15) 0.0634(14) Uani 1 d . . .
N16 N 0.4455(3) 0.8953(7) 0.2093(2) 0.0818(17) Uani 1 d . . .
C24 C 0.2998(3) 0.5815(8) 0.10391(18) 0.0618(16) Uani 1 d . . .
C25 C 0.2797(3) 0.4301(7) 0.1076(2) 0.0689(17) Uani 1 d . . .
C26 C 0.3184(3) 0.4205(6) 0.1764(2) 0.0633(17) Uani 1 d . . .
C27 C 0.3325(2) 0.3385(6) 0.21545(19) 0.0541(14) Uani 1 d . . .
C28 C 0.3177(3) 0.1922(6) 0.2264(2) 0.0723(19) Uani 1 d . . .
H28 H 0.2959 0.1315 0.2071 0.087 Uiso 1 calc . . R
C29 C 0.3355(3) 0.1363(7) 0.2666(2) 0.0675(18) Uani 1 d . . .
H29 H 0.3274 0.0359 0.2738 0.081 Uiso 1 calc . . R
C30 C 0.3653(3) 0.2295(7) 0.2958(2) 0.0686(18) Uani 1 d . . .
H30 H 0.3762 0.1935 0.3232 0.082 Uiso 1 calc . . R
C31 C 0.3788(3) 0.3764(7) 0.2843(2) 0.0633(17) Uani 1 d . . .
C32 C 0.4077(2) 0.4925(6) 0.31101(18) 0.0490(13) Uani 1 d . . .
C33 C 0.4538(3) 0.5778(7) 0.3724(2) 0.0622(16) Uani 1 d . . .
C34 C 0.4602(2) 0.7215(7) 0.3514(2) 0.0604(16) Uani 1 d . . .
C35 C 0.2464(4) 0.3486(9) 0.0715(3) 0.100(3) Uani 1 d . . .
H35 H 0.2424 0.4167 0.0466 0.120 Uiso 1 calc . . R
C36 C 0.2793(8) 0.2116(15) 0.0596(4) 0.222(9) Uani 1 d . . .
H36A H 0.3139 0.2421 0.0462 0.333 Uiso 1 calc . . GR
H36B H 0.2556 0.1505 0.0400 0.333 Uiso 1 calc . . GR
H36C H 0.2896 0.1533 0.0850 0.333 Uiso 1 calc . . GR
C37 C 0.1879(7) 0.308(2) 0.0848(4) 0.241(10) Uani 1 d . . .
H37A H 0.1906 0.2190 0.1030 0.362 Uiso 1 calc . . GR
H37B H 0.1630 0.2860 0.0598 0.362 Uiso 1 calc . . GR
H37C H 0.1722 0.3911 0.1004 0.362 Uiso 1 calc . . GR
C38 C 0.2920(3) 0.6839(8) 0.0652(2) 0.075(2) Uani 1 d . . .
H38 H 0.2933 0.6183 0.0398 0.090 Uiso 1 calc . . R
C39 C 0.3395(5) 0.8007(11) 0.0620(3) 0.142(4) Uani 1 d . . .
H39A H 0.3309 0.8882 0.0790 0.213 Uiso 1 calc . . GR
H39B H 0.3420 0.8308 0.0325 0.213 Uiso 1 calc . . GR
H39C H 0.3759 0.7573 0.0724 0.213 Uiso 1 calc . . GR
C40 C 0.2330(4) 0.7567(11) 0.0634(3) 0.122(3) Uani 1 d . . .
H40A H 0.2038 0.6790 0.0645 0.183 Uiso 1 calc . . GR
H40B H 0.2272 0.8130 0.0370 0.183 Uiso 1 calc . . GR
H40C H 0.2303 0.8246 0.0873 0.183 Uiso 1 calc . . GR
C41 C 0.4689(4) 0.5492(8) 0.4176(2) 0.087(2) Uani 1 d . . .
H41 H 0.4984 0.6241 0.4272 0.105 Uiso 1 calc . . R
C42 C 0.4950(9) 0.3910(18) 0.4244(4) 0.254(10) Uani 1 d . . .
H42A H 0.4844 0.3279 0.4000 0.380 Uiso 1 calc . . GR
H42B H 0.4805 0.3464 0.4498 0.380 Uiso 1 calc . . GR
H42C H 0.5365 0.3988 0.4277 0.380 Uiso 1 calc . . GR
C43 C 0.4209(6) 0.563(2) 0.4448(3) 0.195(6) Uani 1 d . . .
H43A H 0.4065 0.6660 0.4436 0.293 Uiso 1 calc . . GR
H43B H 0.4336 0.5387 0.4739 0.293 Uiso 1 calc . . GR
H43C H 0.3905 0.4945 0.4351 0.293 Uiso 1 calc . . GR
C44 C 0.4907(4) 0.8518(7) 0.3735(2) 0.081(2) Uani 1 d . . .
H44 H 0.4910 0.8249 0.4041 0.097 Uiso 1 calc . . R
C45 C 0.5529(6) 0.845(2) 0.3633(5) 0.255(11) Uani 1 d . . .
H45A H 0.5648 0.7407 0.3612 0.383 Uiso 1 calc . . GR
H45B H 0.5762 0.8949 0.3857 0.383 Uiso 1 calc . . GR
H45C H 0.5579 0.8960 0.3365 0.383 Uiso 1 calc . . GR
C46 C 0.4535(9) 0.9931(14) 0.3700(7) 0.303(14) Uani 1 d . . .
H46A H 0.4537 1.0329 0.3413 0.454 Uiso 1 calc . . GR
H46B H 0.4686 1.0684 0.3900 0.454 Uiso 1 calc . . GR
H46C H 0.4144 0.9680 0.3765 0.454 Uiso 1 calc . . GR
O7 O 0.2090(3) 0.6960(8) 0.1816(2) 0.123(2) Uani 1 d . . .
O8 O 0.2156(3) 0.9320(9) 0.1658(2) 0.130(2) Uani 1 d . . .
O9 O 0.2477(3) 0.8600(6) 0.2271(2) 0.114(2) Uani 1 d . . .
N17 N 0.2236(3) 0.8270(11) 0.1903(2) 0.090(2) Uani 1 d . . .
O10 O 0.2511(3) 0.6331(6) 0.2720(3) 0.1080(19) Uani 1 d A 2 .
O11 O 0.2839(4) 0.5619(9) 0.3338(3) 0.143(3) Uani 1 d A 2 .
O12 O 0.2908(3) 0.7973(8) 0.3181(2) 0.120(2) Uani 1 d A 2 .
N18 N 0.2778(4) 0.6642(12) 0.3111(3) 0.102(2) Uani 1 d A 2 .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd1 O1 2.007(4) . ?
Pd1 N2 2.002(5) . ?
Pd1 N4 1.931(4) . ?
Pd1 N5 2.005(6) . ?
O1 N15 1.283(7) . ?
O2 N15 1.202(7) . ?
O3 N15 1.222(7) . ?
N1 N2 1.349(6) . ?
N1 C1 1.311(7) . ?
N2 C3 1.325(7) . ?
N3 C2 1.328(7) . ?
N3 C3 1.327(8) . ?
N4 C4 1.286(6) . ?
N4 C8 1.374(7) . ?
N5 N6 1.352(7) . ?
N5 C9 1.334(7) . ?
N6 C11 1.307(8) . ?
N7 C9 1.324(7) . ?
N7 C10 1.326(7) . ?
C1 C2 1.417(8) . ?
C1 C12 1.501(8) . ?
C2 C15 1.530(8) . ?
C3 C4 1.494(8) . ?
C4 C5 1.394(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.367(9) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.365(8) . ?
C8 C9 1.488(8) . ?
C10 C11 1.410(9) . ?
C10 C18 1.504(9) . ?
C11 C21 1.527(9) . ?
C12 H12 0.9800 . ?
C12 C13 1.450(14) . ?
C12 C14 1.544(14) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15 0.9800 . ?
C15 C16 1.435(12) . ?
C15 C17 1.490(13) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18 0.9800 . ?
C18 C19 1.497(14) . ?
C18 C20 1.518(14) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21 0.9800 . ?
C21 C22 1.511(11) . ?
C21 C23 1.520(11) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
Pd2 O4 2.017(4) . ?
Pd2 N9 2.041(4) . ?
Pd2 N11 1.935(4) . ?
Pd2 N12 2.047(5) . ?
O4 N16 1.298(7) . ?
O5 N16 1.226(7) . ?
O6 N16 1.203(8) . ?
N8 N9 1.322(6) . ?
N8 C24 1.345(7) . ?
N9 C26 1.357(7) . ?
N10 C25 1.332(8) . ?
N10 C26 1.336(8) . ?
N11 C27 1.331(7) . ?
N11 C31 1.362(8) . ?
N12 N13 1.319(6) . ?
N12 C32 1.356(6) . ?
N13 C34 1.328(8) . ?
N14 C32 1.317(7) . ?
N14 C33 1.326(8) . ?
C24 C25 1.413(9) . ?
C24 C38 1.506(8) . ?
C25 C35 1.505(9) . ?
C26 C27 1.434(8) . ?
C27 C28 1.376(8) . ?
C28 H28 0.9300 . ?
C28 C29 1.383(9) . ?
C29 H29 0.9300 . ?
C29 C30 1.378(9) . ?
C30 H30 0.9300 . ?
C30 C31 1.378(8) . ?
C31 C32 1.453(8) . ?
C33 C34 1.431(9) . ?
C33 C41 1.451(9) . ?
C34 C44 1.490(8) . ?
C35 H35 0.9800 . ?
C35 C36 1.478(15) . ?
C35 C37 1.478(15) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38 0.9800 . ?
C38 C39 1.507(11) . ?
C38 C40 1.499(10) . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 H41 0.9800 . ?
C41 C42 1.522(14) . ?
C41 C43 1.438(13) . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 H44 0.9800 . ?
C44 C45 1.488(14) . ?
C44 C46 1.507(15) . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
O7 N17 1.223(9) . ?
O8 N17 1.204(9) . ?
O9 N17 1.279(9) . ?
O10 N18 1.363(10) . ?
O11 N18 1.146(9) . ?
O12 N18 1.222(9) . ?

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
N2 Pd1 O1 100.15(18) . . ?
N2 Pd1 N5 160.18(18) . . ?
N4 Pd1 O1 174.91(19) . . ?
N4 Pd1 N2 79.39(19) . . ?
N4 Pd1 N5 80.82(19) . . ?
N5 Pd1 O1 99.46(19) . . ?
N15 O1 Pd1 117.0(4) . . ?
C1 N1 N2 119.7(5) . . ?
N1 N2 Pd1 128.5(3) . . ?
C3 N2 Pd1 114.1(4) . . ?
C3 N2 N1 117.4(5) . . ?
C3 N3 C2 115.6(5) . . ?
C4 N4 Pd1 120.6(4) . . ?
C4 N4 C8 122.4(5) . . ?
C8 N4 Pd1 117.0(4) . . ?
N6 N5 Pd1 126.8(4) . . ?
C9 N5 Pd1 115.8(4) . . ?
C9 N5 N6 117.3(5) . . ?
C11 N6 N5 118.5(5) . . ?
C9 N7 C10 116.5(5) . . ?
O2 N15 O1 118.2(6) . . ?
O2 N15 O3 124.2(7) . . ?
O3 N15 O1 117.5(6) . . ?
N1 C1 C2 120.5(5) . . ?
N1 C1 C12 114.4(5) . . ?
C2 C1 C12 125.1(6) . . ?
N3 C2 C1 119.9(5) . . ?
N3 C2 C15 117.9(6) . . ?
C1 C2 C15 122.2(5) . . ?
N2 C3 N3 126.8(6) . . ?
N2 C3 C4 114.9(5) . . ?
N3 C3 C4 118.2(5) . . ?
N4 C4 C3 111.0(5) . . ?
N4 C4 C5 120.4(5) . . ?
C5 C4 C3 128.6(5) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 C4 118.3(6) . . ?
C6 C5 H5 120.8 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.1(6) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 121.1 . . ?
C8 C7 C6 117.9(6) . . ?
C8 C7 H7 121.1 . . ?
N4 C8 C9 112.9(5) . . ?
C7 C8 N4 119.8(5) . . ?
C7 C8 C9 127.2(5) . . ?
N5 C9 C8 113.4(5) . . ?
N7 C9 N5 126.5(5) . . ?
N7 C9 C8 120.1(5) . . ?
N7 C10 C11 118.4(6) . . ?
N7 C10 C18 114.3(6) . . ?
C11 C10 C18 127.3(6) . . ?
N6 C11 C10 122.6(6) . . ?
N6 C11 C21 116.3(6) . . ?
C10 C11 C21 121.0(6) . . ?
C1 C12 H12 102.8 . . ?
C1 C12 C14 107.6(7) . . ?
C13 C12 C1 108.9(8) . . ?
C13 C12 H12 102.8 . . ?
C13 C12 C14 128.8(13) . . ?
C14 C12 H12 102.8 . . ?
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 . . ?
C2 C15 H15 109.9 . . ?
C16 C15 C2 109.1(6) . . ?
C16 C15 H15 109.9 . . ?
C16 C15 C17 107.2(11) . . ?
C17 C15 C2 110.9(7) . . ?
C17 C15 H15 109.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C18 H18 109.2 . . ?
C10 C18 C20 109.6(8) . . ?
C19 C18 C10 109.4(8) . . ?
C19 C18 H18 109.2 . . ?
C19 C18 C20 110.3(11) . . ?
C20 C18 H18 109.2 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C11 C21 H21 107.8 . . ?
C22 C21 C11 109.6(7) . . ?
C22 C21 H21 107.8 . . ?
C22 C21 C23 113.1(8) . . ?
C23 C21 C11 110.5(7) . . ?
C23 C21 H21 107.8 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O4 Pd2 N9 97.79(18) . . ?
O4 Pd2 N12 101.77(17) . . ?
N9 Pd2 N12 160.30(18) . . ?
N11 Pd2 O4 175.13(19) . . ?
N11 Pd2 N9 79.99(18) . . ?
N11 Pd2 N12 80.33(18) . . ?
N16 O4 Pd2 115.5(4) . . ?
N9 N8 C24 118.3(5) . . ?
N8 N9 Pd2 127.1(4) . . ?
N8 N9 C26 121.9(5) . . ?
C26 N9 Pd2 110.9(4) . . ?
C25 N10 C26 117.2(5) . . ?
C27 N11 Pd2 119.6(4) . . ?
C27 N11 C31 122.7(5) . . ?
C31 N11 Pd2 117.7(4) . . ?
N13 N12 Pd2 124.2(4) . . ?
N13 N12 C32 122.2(5) . . ?
C32 N12 Pd2 113.5(3) . . ?
N12 N13 C34 116.2(5) . . ?
C32 N14 C33 117.8(5) . . ?
O5 N16 O4 115.8(7) . . ?
O6 N16 O4 119.0(6) . . ?
O6 N16 O5 125.2(7) . . ?
N8 C24 C25 119.2(6) . . ?
N8 C24 C38 113.9(6) . . ?
C25 C24 C38 126.9(6) . . ?
N10 C25 C24 121.4(6) . . ?
N10 C25 C35 115.9(6) . . ?
C24 C25 C35 122.8(6) . . ?
N9 C26 C27 118.2(6) . . ?
N10 C26 N9 121.9(6) . . ?
N10 C26 C27 119.7(5) . . ?
N11 C27 C26 111.1(5) . . ?
N11 C27 C28 119.6(6) . . ?
C28 C27 C26 129.2(6) . . ?
C27 C28 H28 120.3 . . ?
C27 C28 C29 119.4(6) . . ?
C29 C28 H28 120.3 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 119.9(6) . . ?
C30 C29 H29 120.0 . . ?
C29 C30 H30 120.2 . . ?
C31 C30 C29 119.5(6) . . ?
C31 C30 H30 120.2 . . ?
N11 C31 C30 118.8(6) . . ?
N11 C31 C32 113.7(5) . . ?
C30 C31 C32 127.4(6) . . ?
N12 C32 C31 114.8(5) . . ?
N14 C32 N12 122.9(5) . . ?
N14 C32 C31 122.3(5) . . ?
N14 C33 C34 118.6(6) . . ?
N14 C33 C41 116.1(6) . . ?
C34 C33 C41 124.8(6) . . ?
N13 C34 C33 122.2(6) . . ?
N13 C34 C44 116.4(6) . . ?
C33 C34 C44 121.4(6) . . ?
C25 C35 H35 108.9 . . ?
C36 C35 C25 109.1(8) . . ?
C36 C35 H35 108.9 . . ?
C36 C35 C37 111.2(12) . . ?
C37 C35 C25 109.9(8) . . ?
C37 C35 H35 108.9 . . ?
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 . . ?
C24 C38 H38 106.8 . . ?
C24 C38 C39 113.8(6) . . ?
C39 C38 H38 106.8 . . ?
C40 C38 C24 110.6(6) . . ?
C40 C38 H38 106.8 . . ?
C40 C38 C39 111.7(8) . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C38 C40 H40A 109.5 . . ?
C38 C40 H40B 109.5 . . ?
C38 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C33 C41 H41 107.8 . . ?
C33 C41 C42 111.4(7) . . ?
C42 C41 H41 107.8 . . ?
C43 C41 C33 114.0(8) . . ?
C43 C41 H41 107.8 . . ?
C43 C41 C42 107.9(11) . . ?
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 . . ?
C41 C43 H43A 109.5 . . ?
C41 C43 H43B 109.5 . . ?
C41 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C34 C44 H44 104.0 . . ?
C34 C44 C46 110.2(8) . . ?
C45 C44 C34 107.8(7) . . ?
C45 C44 H44 104.0 . . ?
C45 C44 C46 124.6(13) . . ?
C46 C44 H44 104.0 . . ?
C44 C45 H45A 109.5 . . ?
C44 C45 H45B 109.5 . . ?
C44 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C44 C46 H46A 109.5 . . ?
C44 C46 H46B 109.5 . . ?
C44 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
O7 N17 O9 120.7(8) . . ?
O8 N17 O7 123.3(9) . . ?
O8 N17 O9 116.0(9) . . ?
O11 N18 O10 115.5(10) . . ?
O11 N18 O12 128.0(11) . . ?
O12 N18 O10 116.4(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Pd1 O1 N15 O2 177.2(5) . . . . ?
Pd1 O1 N15 O3 1.1(9) . . . . ?
Pd1 N2 C3 N3 178.0(5) . . . . ?
Pd1 N2 C3 C4 0.7(7) . . . . ?
Pd1 N4 C4 C3 -1.0(6) . . . . ?
Pd1 N4 C4 C5 -179.6(4) . . . . ?
Pd1 N4 C8 C7 -178.2(4) . . . . ?
Pd1 N4 C8 C9 -1.5(6) . . . . ?
Pd1 N5 N6 C11 -178.7(4) . . . . ?
Pd1 N5 C9 N7 -179.2(5) . . . . ?
Pd1 N5 C9 C8 0.6(6) . . . . ?
O1 Pd1 N2 N1 5.4(5) . . . . ?
O1 Pd1 N2 C3 -175.8(4) . . . . ?
O1 Pd1 N4 C4 86(2) . . . . ?
O1 Pd1 N4 C8 -92(2) . . . . ?
O1 Pd1 N5 N6 -6.8(5) . . . . ?
O1 Pd1 N5 C9 173.7(4) . . . . ?
N1 N2 C3 N3 -3.1(10) . . . . ?
N1 N2 C3 C4 179.6(5) . . . . ?
N1 C1 C2 N3 -2.1(9) . . . . ?
N1 C1 C2 C15 179.8(6) . . . . ?
N1 C1 C12 C13 -54.6(13) . . . . ?
N1 C1 C12 C14 88.8(10) . . . . ?
N2 Pd1 O1 N15 -72.1(5) . . . . ?
N2 Pd1 N4 C4 1.1(4) . . . . ?
N2 Pd1 N4 C8 -177.4(4) . . . . ?
N2 Pd1 N5 N6 -178.3(5) . . . . ?
N2 Pd1 N5 C9 2.2(8) . . . . ?
N2 N1 C1 C2 -0.1(8) . . . . ?
N2 N1 C1 C12 -178.1(5) . . . . ?
N2 C3 C4 N4 0.2(8) . . . . ?
N2 C3 C4 C5 178.6(6) . . . . ?
N3 C2 C15 C16 79.3(10) . . . . ?
N3 C2 C15 C17 -38.5(11) . . . . ?
N3 C3 C4 N4 -177.4(5) . . . . ?
N3 C3 C4 C5 1.1(10) . . . . ?
N4 Pd1 O1 N15 -157(2) . . . . ?
N4 Pd1 N2 N1 -179.7(5) . . . . ?
N4 Pd1 N2 C3 -0.9(4) . . . . ?
N4 Pd1 N5 N6 178.4(5) . . . . ?
N4 Pd1 N5 C9 -1.1(4) . . . . ?
N4 C4 C5 C6 0.2(9) . . . . ?
N4 C8 C9 N5 0.5(7) . . . . ?
N4 C8 C9 N7 -179.7(5) . . . . ?
N5 Pd1 O1 N15 110.8(5) . . . . ?
N5 Pd1 N2 N1 176.9(5) . . . . ?
N5 Pd1 N2 C3 -4.3(9) . . . . ?
N5 Pd1 N4 C4 180.0(5) . . . . ?
N5 Pd1 N4 C8 1.4(4) . . . . ?
N5 N6 C11 C10 -3.0(10) . . . . ?
N5 N6 C11 C21 -179.4(6) . . . . ?
N6 N5 C9 N7 1.3(9) . . . . ?
N6 N5 C9 C8 -178.9(5) . . . . ?
N6 C11 C21 C22 95.6(8) . . . . ?
N6 C11 C21 C23 -29.7(10) . . . . ?
N7 C10 C11 N6 3.3(10) . . . . ?
N7 C10 C11 C21 179.6(7) . . . . ?
N7 C10 C18 C19 -61.8(12) . . . . ?
N7 C10 C18 C20 59.3(10) . . . . ?
C1 N1 N2 Pd1 -178.7(4) . . . . ?
C1 N1 N2 C3 2.5(8) . . . . ?
C1 C2 C15 C16 -102.6(10) . . . . ?
C1 C2 C15 C17 139.6(10) . . . . ?
C2 N3 C3 N2 0.9(9) . . . . ?
C2 N3 C3 C4 178.1(5) . . . . ?
C2 C1 C12 C13 127.5(12) . . . . ?
C2 C1 C12 C14 -89.1(11) . . . . ?
C3 N3 C2 C1 1.7(8) . . . . ?
C3 N3 C2 C15 179.8(6) . . . . ?
C3 C4 C5 C6 -178.1(6) . . . . ?
C4 N4 C8 C7 3.3(9) . . . . ?
C4 N4 C8 C9 180.0(5) . . . . ?
C4 C5 C6 C7 -1.3(10) . . . . ?
C5 C6 C7 C8 3.3(10) . . . . ?
C6 C7 C8 N4 -4.2(9) . . . . ?
C6 C7 C8 C9 179.6(6) . . . . ?
C7 C8 C9 N5 177.0(6) . . . . ?
C7 C8 C9 N7 -3.2(9) . . . . ?
C8 N4 C4 C3 177.4(5) . . . . ?
C8 N4 C4 C5 -1.2(9) . . . . ?
C9 N5 N6 C11 0.7(8) . . . . ?
C9 N7 C10 C11 -1.3(9) . . . . ?
C9 N7 C10 C18 -179.9(6) . . . . ?
C10 N7 C9 N5 -0.9(9) . . . . ?
C10 N7 C9 C8 179.3(6) . . . . ?
C10 C11 C21 C22 -80.8(9) . . . . ?
C10 C11 C21 C23 153.9(7) . . . . ?
C11 C10 C18 C19 119.7(11) . . . . ?
C11 C10 C18 C20 -119.2(10) . . . . ?
C12 C1 C2 N3 175.7(6) . . . . ?
C12 C1 C2 C15 -2.4(10) . . . . ?
C18 C10 C11 N6 -178.2(8) . . . . ?
C18 C10 C11 C21 -2.0(11) . . . . ?
Pd2 O4 N16 O5 -176.7(5) . . . . ?
Pd2 O4 N16 O6 1.2(9) . . . . ?
Pd2 N9 C26 N10 -179.9(5) . . . . ?
Pd2 N9 C26 C27 -3.0(7) . . . . ?
Pd2 N11 C27 C26 -0.6(7) . . . . ?
Pd2 N11 C27 C28 -177.8(5) . . . . ?
Pd2 N11 C31 C30 178.8(5) . . . . ?
Pd2 N11 C31 C32 1.5(7) . . . . ?
Pd2 N12 N13 C34 -179.6(4) . . . . ?
Pd2 N12 C32 N14 -178.9(5) . . . . ?
Pd2 N12 C32 C31 2.1(6) . . . . ?
O4 Pd2 N9 N8 7.1(5) . . . . ?
O4 Pd2 N9 C26 -173.6(4) . . . . ?
O4 Pd2 N11 C27 62(2) . . . . ?
O4 Pd2 N11 C31 -116(2) . . . . ?
O4 Pd2 N12 N13 -2.3(4) . . . . ?
O4 Pd2 N12 C32 174.5(4) . . . . ?
N8 N9 C26 N10 -0.5(9) . . . . ?
N8 N9 C26 C27 176.3(5) . . . . ?
N8 C24 C25 N10 0.0(10) . . . . ?
N8 C24 C25 C35 -179.9(7) . . . . ?
N8 C24 C38 C39 28.3(10) . . . . ?
N8 C24 C38 C40 -98.4(7) . . . . ?
N9 Pd2 O4 N16 -113.0(4) . . . . ?
N9 Pd2 N11 C27 -0.7(4) . . . . ?
N9 Pd2 N11 C31 -179.4(5) . . . . ?
N9 Pd2 N12 N13 -175.4(5) . . . . ?
N9 Pd2 N12 C32 1.5(7) . . . . ?
N9 N8 C24 C25 -0.9(8) . . . . ?
N9 N8 C24 C38 179.1(5) . . . . ?
N9 C26 C27 N11 2.5(8) . . . . ?
N9 C26 C27 C28 179.3(6) . . . . ?
N10 C25 C35 C36 -60.4(11) . . . . ?
N10 C25 C35 C37 61.7(12) . . . . ?
N10 C26 C27 N11 179.4(6) . . . . ?
N10 C26 C27 C28 -3.8(11) . . . . ?
N11 Pd2 O4 N16 -176(21) . . . . ?
N11 Pd2 N9 N8 -177.3(5) . . . . ?
N11 Pd2 N9 C26 2.0(4) . . . . ?
N11 Pd2 N12 N13 -177.9(4) . . . . ?
N11 Pd2 N12 C32 -1.0(4) . . . . ?
N11 C27 C28 C29 -2.6(10) . . . . ?
N11 C31 C32 N12 -2.3(7) . . . . ?
N11 C31 C32 N14 178.6(5) . . . . ?
N12 Pd2 O4 N16 69.4(5) . . . . ?
N12 Pd2 N9 N8 -179.8(4) . . . . ?
N12 Pd2 N9 C26 -0.5(7) . . . . ?
N12 Pd2 N11 C27 178.4(5) . . . . ?
N12 Pd2 N11 C31 -0.3(4) . . . . ?
N12 N13 C34 C33 -2.7(8) . . . . ?
N12 N13 C34 C44 177.2(5) . . . . ?
N13 N12 C32 N14 -1.9(8) . . . . ?
N13 N12 C32 C31 179.0(5) . . . . ?
N13 C34 C44 C45 -87.8(11) . . . . ?
N13 C34 C44 C46 51.2(13) . . . . ?
N14 C33 C34 N13 -0.4(9) . . . . ?
N14 C33 C34 C44 179.7(6) . . . . ?
N14 C33 C41 C42 45.4(13) . . . . ?
N14 C33 C41 C43 -76.9(11) . . . . ?
C24 N8 N9 Pd2 -179.6(4) . . . . ?
C24 N8 N9 C26 1.2(8) . . . . ?
C24 C25 C35 C36 119.5(10) . . . . ?
C24 C25 C35 C37 -118.3(11) . . . . ?
C25 N10 C26 N9 -0.4(10) . . . . ?
C25 N10 C26 C27 -177.2(6) . . . . ?
C25 C24 C38 C39 -151.7(8) . . . . ?
C25 C24 C38 C40 81.7(9) . . . . ?
C26 N10 C25 C24 0.7(10) . . . . ?
C26 N10 C25 C35 -179.4(7) . . . . ?
C26 C27 C28 C29 -179.1(7) . . . . ?
C27 N11 C31 C30 0.2(9) . . . . ?
C27 N11 C31 C32 -177.2(5) . . . . ?
C27 C28 C29 C30 3.2(11) . . . . ?
C28 C29 C30 C31 -2.2(11) . . . . ?
C29 C30 C31 N11 0.5(10) . . . . ?
C29 C30 C31 C32 177.4(6) . . . . ?
C30 C31 C32 N12 -179.4(6) . . . . ?
C30 C31 C32 N14 1.5(10) . . . . ?
C31 N11 C27 C26 178.0(5) . . . . ?
C31 N11 C27 C28 0.9(9) . . . . ?
C32 N12 N13 C34 3.8(8) . . . . ?
C32 N14 C33 C34 2.4(9) . . . . ?
C32 N14 C33 C41 174.8(6) . . . . ?
C33 N14 C32 N12 -1.3(9) . . . . ?
C33 N14 C32 C31 177.6(6) . . . . ?
C33 C34 C44 C45 92.1(11) . . . . ?
C33 C34 C44 C46 -128.9(12) . . . . ?
C34 C33 C41 C42 -142.7(11) . . . . ?
C34 C33 C41 C43 95.0(11) . . . . ?
C38 C24 C25 N10 179.9(7) . . . . ?
C38 C24 C25 C35 0.0(11) . . . . ?
C41 C33 C34 N13 -172.1(7) . . . . ?
C41 C33 C34 C44 8.0(11) . . . . ?

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.500 154 23 ' '
2 0.500 0.000 0.500 155 22 ' '
3 0.350 0.051 0.143 10 1 ' '
4 0.146 0.062 0.859 9 1 ' '
5 0.500 0.500 0.000 155 22 ' '
6 0.000 0.500 1.000 154 23 ' '
7 0.146 0.437 0.359 9 1 ' '
8 0.350 0.449 0.643 10 1 ' '
9 0.650 0.550 0.357 10 1 ' '
10 0.854 0.562 0.641 9 1 ' '
11 0.854 0.937 0.141 9 1 ' '
12 0.650 0.949 0.857 10 1 ' '
_platon_squeeze_details          
;
;
_exptl_crystal_recrystallization_method 'Vapour Deposition'
_chemical_properties_physical    'Heat-sensitive, Light-sensitive'
####################################################################### 
# 
# 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_150331_subt_btp
_database_code_depnum_ccdc_archive 'CCDC 1429208'
_audit_update_record             
;
2015-10-02 deposited with the CCDC.	2019-05-07 downloaded from the CCDC.
;
_audit_creation_date             2015-04-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_chemical_name_common            ?
_chemical_name_systematic        subt-BTP
_chemical_formula_moiety         'C27 H39 N7, H2 O'
_chemical_formula_sum            'C27 H41 N7 O'
_chemical_formula_weight         479.67
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   13.5131(6)
_cell_length_b                   16.9916(5)
_cell_length_c                   26.0514(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5981.7(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7648
_cell_measurement_temperature    172.0
_cell_measurement_theta_max      29.5597
_cell_measurement_theta_min      2.8567
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.065
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.43
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            37634
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.86
_diffrn_ambient_temperature      172.0
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -64.00   40.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8433  -77.0000  -90.0000 104

#__ type_ start__ end____ width___ exp.time_
  2 omega  -85.00   21.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.7183  -77.0000    0.0000 106

#__ type_ start__ end____ width___ exp.time_
  3 omega  -48.00   37.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.7183   84.0000  136.0000 85
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0511769000
_diffrn_orient_matrix_UB_12      -0.0031689000
_diffrn_orient_matrix_UB_13      0.0056474000
_diffrn_orient_matrix_UB_21      -0.0114953000
_diffrn_orient_matrix_UB_22      0.0194009000
_diffrn_orient_matrix_UB_23      -0.0233625000
_diffrn_orient_matrix_UB_31      -0.0016633000
_diffrn_orient_matrix_UB_32      -0.0368318000
_diffrn_orient_matrix_UB_33      -0.0127960000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3930
_reflns_number_total             5444
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     483
_refine_ls_number_reflns         5444
_refine_ls_number_restraints     614
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0699
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1156P)²+3.0892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1928
_refine_ls_wR_factor_ref         0.2166
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Shared sites
{H13, H13A}
2. Others
 Fixed Uiso: H1A(0.063) H1B(0.063) H3(0.053) H4(0.046) H2(0.048) H20(0.09)
 H24(0.073) H13(0.135) H26A(0.083) H26B(0.083) H21A(0.122) H21B(0.122)
 H21C(0.122) H9(0.075) H25A(0.119) H25B(0.119) H25C(0.119) H12A(0.13)
 H12B(0.13) H12C(0.13) H22A(0.113) H22B(0.113) H10A(0.138) H10B(0.138)
 H10C(0.138) H11A(0.083) H11B(0.083) H14A(0.196) H14B(0.196) H14C(0.196)
 H27A(0.163) H27B(0.163) H27C(0.163) H15A(0.149) H15B(0.149) H23A(0.171)
 H23B(0.171) H23C(0.171) H16A(0.222) H16B(0.222) H16C(0.222) H26C(0.098)
 H26D(0.098) H24A(0.09) H27D(0.157) H27E(0.157) H27F(0.157) H25D(0.138)
 H25E(0.138) H25F(0.138) H21D(0.122) H21E(0.122) H21F(0.122) H20A(0.094)
 H22C(0.112) H22D(0.112) H23D(0.15) H23E(0.15) H23F(0.15) H11C(0.084)
 H11D(0.084) H9A(0.075) H10D(0.125) H10E(0.125) H10F(0.125) H12D(0.116)
 H12E(0.116) H12F(0.116) H13A(0.139) H15C(0.151) H15D(0.151) H14D(0.197)
 H14E(0.197) H14F(0.197) H16D(0.215) H16E(0.215) H16F(0.215)
 Fixed X: H1A(0.8826) H1B(0.8021) H3(0.8011) H4(0.7037) H2(0.9144) H20(1.1874)
 H24(1.184) H13(0.5027) H26A(1.1005) H26B(1.1728) H21A(1.0201) H21B(1.0672)
 H21C(0.9821) H9(0.5) H25A(1.2824) H25B(1.3066) H25C(1.2376) H12A(0.3584)
 H12B(0.4407) H12C(0.3693) H22A(1.085) H22B(1.1658) H10A(0.674) H10B(0.5841)
 H10C(0.6482) H11A(0.4413) H11B(0.5143) H14A(0.6736) H14B(0.5926) H14C(0.6586)
 H27A(0.9795) H27B(1.0168) H27C(1.0529) H15A(0.4495) H15B(0.537) H23A(1.2099)
 H23B(1.275) H23C(1.2832) H16A(0.3794) H16B(0.3873) H16C(0.4666) H26C(1.2572)
 H26D(1.1788) H24A(1.1858) H27D(1.2959) H27E(1.3469) H27F(1.2488) H25D(1.0564)
 H25E(1.1392) H25F(1.0442) H21D(1.1365) H21E(1.2092) H21F(1.2332) H20A(1.1555)
 H22C(1.0972) H22D(1.0099) H23D(0.9655) H23E(1.0519) H23F(0.9553) H11C(0.4855)
 H11D(0.5755) H9A(0.4639) H10D(0.444) H10E(0.3573) H10F(0.3834) H12D(0.5804)
 H12E(0.6731) H12F(0.6064) H13A(0.493) H15C(0.6272) H15D(0.5497) H14D(0.42)
 H14E(0.4246) H14F(0.5028) H16D(0.6495) H16E(0.7284) H16F(0.7171)
 Fixed Y: H1A(0.3063) H1B(0.313) H3(-0.0662) H4(0.0199) H2(-0.0133)
 H20(0.0865) H24(0.2161) H13(0.3168) H26A(0.3568) H26B(0.3527) H21A(0.0908)
 H21B(0.0053) H21C(0.0181) H9(0.2017) H25A(0.2157) H25B(0.2918) H25C(0.2994)
 H12A(0.1653) H12B(0.1715) H12C(0.0964) H22A(-0.0342) H22B(-0.047) H10A(0.1464)
 H10B(0.0933) H10C(0.0654) H11A(0.0693) H11B(0.0566) H14A(0.4118) H14B(0.4323)
 H14C(0.3546) H27A(0.2897) H27B(0.3567) H27C(0.2677) H15A(0.4254) H15B(0.4321)
 H23A(0.0362) H23B(-0.0349) H23C(0.0505) H16A(0.3181) H16B(0.3949) H16C(0.3256)
 H26C(0.3288) H26D(0.3367) H24A(0.204) H27D(0.1913) H27E(0.2659) H27F(0.2285)
 H25D(0.3347) H25E(0.3149) H25F(0.2594) H21D(-0.0247) H21E(-0.0404)
 H21F(0.0285) H20A(0.0959) H22C(-0.0244) H22D(-0.0137) H23D(0.1193)
 H23E(0.1091) H23F(0.0548) H11C(0.0633) H11D(0.0543) H9A(0.1984) H10D(0.0737)
 H10E(0.0911) H10F(0.1545) H12D(0.1392) H12E(0.1202) H12F(0.1962) H13A(0.3139)
 H15C(0.4363) H15D(0.4419) H14D(0.3394) H14E(0.4183) H14F(0.4042) H16D(0.3388)
 H16E(0.3373) H16F(0.4143)
 Fixed Z: H1A(0.6478) H1B(0.6151) H3(0.6033) H4(0.5542) H2(0.662) H20(0.7943)
 H24(0.8051) H13(0.4413) H26A(0.7652) H26B(0.8139) H21A(0.8411) H21B(0.8492)
 H21C(0.8073) H9(0.4234) H25A(0.7284) H25B(0.7623) H25C(0.7127) H12A(0.4729)
 H12B(0.5169) H12C(0.5145) H22A(0.7447) H22B(0.79) H10A(0.3907) H10B(0.3707)
 H10C(0.419) H11A(0.4323) H11B(0.4806) H14A(0.4604) H14B(0.4176) H14C(0.4123)
 H27A(0.8076) H27B(0.8462) H27C(0.8536) H15A(0.4712) H15B(0.5122) H23A(0.6886)
 H23B(0.7105) H23C(0.7359) H16A(0.519) H16B(0.5543) H16C(0.5603) H26C(0.7761)
 H26D(0.7298) H24A(0.7987) H27D(0.735) H27E(0.7085) H27F(0.6842) H25D(0.8)
 H25E(0.842) H25F(0.8363) H21D(0.7219) H21E(0.7693) H21F(0.7294) H20A(0.8092)
 H22C(0.829) H22D(0.7867) H23D(0.8263) H23E(0.8678) H23F(0.8707) H11C(0.4151)
 H11D(0.4559) H9A(0.4417) H10D(0.5265) H10E(0.4862) H10F(0.5296) H12D(0.3634)
 H12E(0.3995) H12F(0.4104) H13A(0.4498) H15C(0.4813) H15D(0.4349) H14D(0.5306)
 H14E(0.4972) H14F(0.5424) H16D(0.386) H16E(0.4318) H16F(0.3969)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
N1 N 0.82881(12) 0.15157(9) 0.61739(6) 0.0287(4) Uani 1 d . . .
O1 O 0.84055(12) 0.33800(9) 0.63509(6) 0.0420(4) Uani 1 d . . .
H1A H 0.8826 0.3063 0.6478 0.063 Uiso 1 d . . G
H1B H 0.8021 0.3130 0.6151 0.063 Uiso 1 d . . G
C1 C 0.88363(15) 0.10141(12) 0.64501(7) 0.0293(5) Uani 1 d . . .
C5 C 0.76319(15) 0.12031(11) 0.58462(7) 0.0303(5) Uani 1 d . . .
C17 C 0.95683(16) 0.13756(12) 0.68089(8) 0.0328(5) Uani 1 d . . .
C6 C 0.70231(17) 0.17684(12) 0.55438(9) 0.0379(5) Uani 1 d . . .
N5 N 1.00371(16) 0.08877(11) 0.71303(8) 0.0471(5) Uani 1 d . . .
N6 N 0.97186(16) 0.21386(11) 0.67757(8) 0.0492(6) Uani 1 d . . .
C3 C 0.80786(18) -0.01084(13) 0.60698(9) 0.0440(6) Uani 1 d . . .
H3 H 0.8011 -0.0662 0.6033 0.053 Uiso 1 calc . . R
C4 C 0.75068(17) 0.03975(13) 0.57809(8) 0.0380(5) Uani 1 d . . .
H4 H 0.7037 0.0199 0.5542 0.046 Uiso 1 calc . . R
N2 N 0.64304(18) 0.14647(12) 0.51852(9) 0.0580(7) Uani 1 d . . .
C2 C 0.87487(17) 0.02026(13) 0.64127(9) 0.0397(5) Uani 1 d . . .
H2 H 0.9144 -0.0133 0.6620 0.048 Uiso 1 calc . . R
N7 N 1.03777(18) 0.24650(12) 0.70945(9) 0.0599(7) Uani 1 d B . .
C19 C 1.0856(2) 0.20235(14) 0.74326(10) 0.0502(7) Uani 1 d . . .
N3 N 0.71087(18) 0.25234(12) 0.56474(9) 0.0584(7) Uani 1 d . . .
C18 C 1.0686(2) 0.12078(14) 0.74501(10) 0.0509(7) Uani 1 d A . .
C20 C 1.1268(19) 0.0622(14) 0.7791(10) 0.075(3) Uani 0.490(9) d A 1 .
H20 H 1.1874 0.0865 0.7943 0.090 Uiso 0.490(9) calc A 1 R
C24 C 1.1636(7) 0.2490(5) 0.7751(4) 0.0609(14) Uani 0.740(7) d B 1 .
H24 H 1.1840 0.2161 0.8051 0.073 Uiso 0.740(7) calc B 1 R
N4 N 0.6568(2) 0.30327(13) 0.53682(11) 0.0799(9) Uani 1 d C . .
C8 C 0.5971(2) 0.27714(16) 0.50042(13) 0.0725(10) Uani 1 d . . .
C7 C 0.5890(2) 0.19686(16) 0.49134(13) 0.0694(9) Uani 1 d C . .
C13 C 0.547(2) 0.3431(13) 0.4666(9) 0.112(3) Uani 0.529(11) d C 1 .
H13 H 0.5027 0.3168 0.4413 0.135 Uiso 0.529(11) calc C 1 R
C26 C 1.1215(4) 0.3236(3) 0.7945(2) 0.0693(13) Uani 0.740(7) d B 1 .
H26A H 1.1005 0.3568 0.7652 0.083 Uiso 0.740(7) calc B 1 R
H26B H 1.1728 0.3527 0.8139 0.083 Uiso 0.740(7) calc B 1 R
C21 C 1.0399(9) 0.0420(7) 0.8239(4) 0.081(3) Uani 0.490(9) d A 1 .
H21A H 1.0201 0.0908 0.8411 0.122 Uiso 0.490(9) calc A 1 GR
H21B H 1.0672 0.0053 0.8492 0.122 Uiso 0.490(9) calc A 1 GR
H21C H 0.9821 0.0181 0.8073 0.122 Uiso 0.490(9) calc A 1 GR
C9 C 0.5394(6) 0.1613(4) 0.4424(3) 0.0627(17) Uani 0.578(8) d C 1 .
H9 H 0.5000 0.2017 0.4234 0.075 Uiso 0.578(8) calc C 1 R
C25 C 1.2560(4) 0.2655(4) 0.7415(2) 0.0795(16) Uani 0.740(7) d B 1 .
H25A H 1.2824 0.2157 0.7284 0.119 Uiso 0.740(7) calc B 1 GR
H25B H 1.3066 0.2918 0.7623 0.119 Uiso 0.740(7) calc B 1 GR
H25C H 1.2376 0.2994 0.7127 0.119 Uiso 0.740(7) calc B 1 GR
C12 C 0.4053(12) 0.1354(7) 0.4940(5) 0.087(3) Uani 0.578(8) d C 1 .
H12A H 0.3584 0.1653 0.4729 0.130 Uiso 0.578(8) calc C 1 GR
H12B H 0.4407 0.1715 0.5169 0.130 Uiso 0.578(8) calc C 1 GR
H12C H 0.3693 0.0964 0.5145 0.130 Uiso 0.578(8) calc C 1 GR
C22 C 1.1433(10) -0.0114(7) 0.7623(5) 0.095(3) Uani 0.490(9) d A 1 .
H22A H 1.0850 -0.0342 0.7447 0.113 Uiso 0.490(9) calc A 1 R
H22B H 1.1658 -0.0470 0.7900 0.113 Uiso 0.490(9) calc A 1 R
C10 C 0.6203(11) 0.1111(6) 0.4011(6) 0.092(3) Uani 0.578(8) d C 1 .
H10A H 0.6740 0.1464 0.3907 0.138 Uiso 0.578(8) calc C 1 GR
H10B H 0.5841 0.0933 0.3707 0.138 Uiso 0.578(8) calc C 1 GR
H10C H 0.6482 0.0654 0.4190 0.138 Uiso 0.578(8) calc C 1 GR
C11 C 0.4753(5) 0.0959(3) 0.4611(3) 0.0692(17) Uani 0.578(8) d C 1 .
H11A H 0.4413 0.0693 0.4323 0.083 Uiso 0.578(8) calc C 1 R
H11B H 0.5143 0.0566 0.4806 0.083 Uiso 0.578(8) calc C 1 R
C14 C 0.6250(11) 0.3896(7) 0.4365(6) 0.131(4) Uani 0.529(11) d C 1 .
H14A H 0.6736 0.4118 0.4604 0.196 Uiso 0.529(11) calc C 1 GR
H14B H 0.5926 0.4323 0.4176 0.196 Uiso 0.529(11) calc C 1 GR
H14C H 0.6586 0.3546 0.4123 0.196 Uiso 0.529(11) calc C 1 GR
C27 C 1.0354(5) 0.3081(4) 0.8283(3) 0.108(2) Uani 0.740(7) d B 1 .
H27A H 0.9795 0.2897 0.8076 0.163 Uiso 0.740(7) calc B 1 GR
H27B H 1.0168 0.3567 0.8462 0.163 Uiso 0.740(7) calc B 1 GR
H27C H 1.0529 0.2677 0.8536 0.163 Uiso 0.740(7) calc B 1 GR
C15 C 0.4920(13) 0.3947(7) 0.4948(5) 0.124(4) Uani 0.529(11) d C 1 .
H15A H 0.4495 0.4254 0.4712 0.149 Uiso 0.529(11) calc C 1 R
H15B H 0.5370 0.4321 0.5122 0.149 Uiso 0.529(11) calc C 1 R
C23 C 1.2383(9) 0.0128(6) 0.7196(4) 0.114(3) Uani 0.490(9) d A 1 .
H23A H 1.2099 0.0362 0.6886 0.171 Uiso 0.490(9) calc A 1 GR
H23B H 1.2750 -0.0349 0.7105 0.171 Uiso 0.490(9) calc A 1 GR
H23C H 1.2832 0.0505 0.7359 0.171 Uiso 0.490(9) calc A 1 GR
C16 C 0.4251(11) 0.3546(7) 0.5359(6) 0.148(4) Uani 0.529(11) d C 1 .
H16A H 0.3794 0.3181 0.5190 0.222 Uiso 0.529(11) calc C 1 GR
H16B H 0.3873 0.3949 0.5543 0.222 Uiso 0.529(11) calc C 1 GR
H16C H 0.4666 0.3256 0.5603 0.222 Uiso 0.529(11) calc C 1 GR
C26A C 1.2158(12) 0.2990(9) 0.7515(6) 0.081(3) Uani 0.260(7) d B 2 D
H26C H 1.2572 0.3288 0.7761 0.098 Uiso 0.260(7) calc B 2 R
H26D H 1.1788 0.3367 0.7298 0.098 Uiso 0.260(7) calc B 2 R
C24A C 1.145(2) 0.2435(17) 0.7796(14) 0.075(3) Uani 0.260(7) d B 2 D
H24A H 1.1858 0.2040 0.7987 0.090 Uiso 0.260(7) calc B 2 R
C27A C 1.2836(13) 0.2403(11) 0.7163(7) 0.105(4) Uani 0.260(7) d B 2 D
H27D H 1.2959 0.1913 0.7350 0.157 Uiso 0.260(7) calc B 2 GR
H27E H 1.3469 0.2659 0.7085 0.157 Uiso 0.260(7) calc B 2 GR
H27F H 1.2488 0.2285 0.6842 0.157 Uiso 0.260(7) calc B 2 GR
C25A C 1.0917(14) 0.2922(13) 0.8177(8) 0.092(4) Uani 0.260(7) d B 2 D
H25D H 1.0564 0.3347 0.8000 0.138 Uiso 0.260(7) calc B 2 GR
H25E H 1.1392 0.3149 0.8420 0.138 Uiso 0.260(7) calc B 2 GR
H25F H 1.0442 0.2594 0.8363 0.138 Uiso 0.260(7) calc B 2 GR
C21A C 1.1802(8) 0.0001(7) 0.7472(4) 0.082(3) Uani 0.510(9) d A 2 .
H21D H 1.1365 -0.0247 0.7219 0.122 Uiso 0.510(9) calc A 2 GR
H21E H 1.2092 -0.0404 0.7693 0.122 Uiso 0.510(9) calc A 2 GR
H21F H 1.2332 0.0285 0.7294 0.122 Uiso 0.510(9) calc A 2 GR
C20A C 1.1116(17) 0.0666(14) 0.7849(10) 0.079(3) Uani 0.510(9) d A 2 .
H20A H 1.1555 0.0959 0.8092 0.094 Uiso 0.510(9) calc A 2 R
C22A C 1.0571(10) 0.0140(6) 0.8095(5) 0.093(3) Uani 0.510(9) d A 2 .
H22C H 1.0972 -0.0244 0.8290 0.112 Uiso 0.510(9) calc A 2 R
H22D H 1.0099 -0.0137 0.7867 0.112 Uiso 0.510(9) calc A 2 R
C23A C 1.0016(8) 0.0814(6) 0.8476(3) 0.100(3) Uani 0.510(9) d A 2 .
H23D H 0.9655 0.1193 0.8263 0.150 Uiso 0.510(9) calc A 2 GR
H23E H 1.0519 0.1091 0.8678 0.150 Uiso 0.510(9) calc A 2 GR
H23F H 0.9553 0.0548 0.8707 0.150 Uiso 0.510(9) calc A 2 GR
C11A C 0.5376(8) 0.0917(5) 0.4344(3) 0.070(2) Uani 0.422(8) d C 2 .
H11C H 0.4855 0.0633 0.4151 0.084 Uiso 0.422(8) calc C 2 R
H11D H 0.5755 0.0543 0.4559 0.084 Uiso 0.422(8) calc C 2 R
C9A C 0.4972(8) 0.1595(6) 0.4647(4) 0.063(2) Uani 0.422(8) d C 2 .
H9A H 0.4639 0.1984 0.4417 0.075 Uiso 0.422(8) calc C 2 R
C10A C 0.4109(16) 0.1147(10) 0.5064(7) 0.083(3) Uani 0.422(8) d C 2 .
H10D H 0.4440 0.0737 0.5265 0.125 Uiso 0.422(8) calc C 2 GR
H10E H 0.3573 0.0911 0.4862 0.125 Uiso 0.422(8) calc C 2 GR
H10F H 0.3834 0.1545 0.5296 0.125 Uiso 0.422(8) calc C 2 GR
C12A C 0.6057(13) 0.1414(8) 0.3986(7) 0.078(3) Uani 0.422(8) d C 2 .
H12D H 0.5804 0.1392 0.3634 0.116 Uiso 0.422(8) calc C 2 GR
H12E H 0.6731 0.1202 0.3995 0.116 Uiso 0.422(8) calc C 2 GR
H12F H 0.6064 0.1962 0.4104 0.116 Uiso 0.422(8) calc C 2 GR
C13A C 0.534(2) 0.3386(14) 0.4775(10) 0.116(4) Uani 0.471(11) d C 2 D
H13A H 0.4930 0.3139 0.4498 0.139 Uiso 0.471(11) calc C 2 R
C15A C 0.5945(13) 0.4058(8) 0.4537(6) 0.126(4) Uani 0.471(11) d C 2 D
H15C H 0.6272 0.4363 0.4813 0.151 Uiso 0.471(11) calc C 2 R
H15D H 0.5497 0.4419 0.4349 0.151 Uiso 0.471(11) calc C 2 R
C14A C 0.4641(13) 0.3787(9) 0.5153(6) 0.131(5) Uani 0.471(11) d C 2 D
H14D H 0.4200 0.3394 0.5306 0.197 Uiso 0.471(11) calc C 2 GR
H14E H 0.4246 0.4183 0.4972 0.197 Uiso 0.471(11) calc C 2 GR
H14F H 0.5028 0.4042 0.5424 0.197 Uiso 0.471(11) calc C 2 GR
C16A C 0.6816(12) 0.3703(7) 0.4128(5) 0.143(4) Uani 0.471(11) d C 2 .
H16D H 0.6495 0.3388 0.3860 0.215 Uiso 0.471(11) calc C 2 GR
H16E H 0.7284 0.3373 0.4318 0.215 Uiso 0.471(11) calc C 2 GR
H16F H 0.7171 0.4143 0.3969 0.215 Uiso 0.471(11) calc C 2 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
N1 C1 1.339(3) . ?
N1 C5 1.341(3) . ?
O1 H1A 0.8502 . ?
O1 H1B 0.8498 . ?
C1 C17 1.493(3) . ?
C1 C2 1.387(3) . ?
C5 C6 1.490(3) . ?
C5 C4 1.390(3) . ?
C17 N5 1.338(3) . ?
C17 N6 1.315(3) . ?
C6 N2 1.334(3) . ?
C6 N3 1.316(3) . ?
N5 C18 1.326(3) . ?
N6 N7 1.338(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(3) . ?
C3 C2 1.377(3) . ?
C4 H4 0.9500 . ?
N2 C7 1.329(3) . ?
C2 H2 0.9500 . ?
N7 C19 1.325(3) . ?
C19 C18 1.406(3) . ?
C19 C24 1.557(10) . ?
C19 C24A 1.43(4) . ?
N3 N4 1.346(3) . ?
C18 C20 1.55(2) . ?
C18 C20A 1.51(2) . ?
C20 H20 1.0000 . ?
C20 C21 1.69(3) . ?
C20 C22 1.34(3) . ?
C24 H24 1.0000 . ?
C24 C26 1.479(9) . ?
C24 C25 1.550(9) . ?
N4 C8 1.321(3) . ?
C8 C7 1.389(4) . ?
C8 C13 1.58(2) . ?
C8 C13A 1.48(3) . ?
C7 C9 1.563(6) . ?
C7 C9A 1.558(9) . ?
C13 H13 1.0000 . ?
C13 C14 1.53(2) . ?
C13 C15 1.37(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.484(10) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C9 H9 1.0000 . ?
C9 C10 1.754(15) . ?
C9 C11 1.491(10) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12 C11 1.441(17) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.746(17) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.56(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C26A H26C 0.9900 . ?
C26A H26D 0.9900 . ?
C26A C24A 1.529(19) . ?
C26A C27A 1.636(17) . ?
C24A H24A 1.0000 . ?
C24A C25A 1.481(19) . ?
C27A H27D 0.9800 . ?
C27A H27E 0.9800 . ?
C27A H27F 0.9800 . ?
C25A H25D 0.9800 . ?
C25A H25E 0.9800 . ?
C25A H25F 0.9800 . ?
C21A H21D 0.9800 . ?
C21A H21E 0.9800 . ?
C21A H21F 0.9800 . ?
C21A C20A 1.76(3) . ?
C20A H20A 1.0000 . ?
C20A C22A 1.32(3) . ?
C22A H22C 0.9900 . ?
C22A H22D 0.9900 . ?
C22A C23A 1.690(16) . ?
C23A H23D 0.9800 . ?
C23A H23E 0.9800 . ?
C23A H23F 0.9800 . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C11A C9A 1.500(15) . ?
C11A C12A 1.56(2) . ?
C9A H9A 1.0000 . ?
C9A C10A 1.77(2) . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 0.9800 . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?
C13A H13A 1.0000 . ?
C13A C15A 1.538(18) . ?
C13A C14A 1.523(19) . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?
C15A C16A 1.70(2) . ?
C14A H14D 0.9800 . ?
C14A H14E 0.9800 . ?
C14A H14F 0.9800 . ?
C16A H16D 0.9800 . ?
C16A H16E 0.9800 . ?
C16A H16F 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
C1 N1 C5 117.13(17) . . ?
H1A O1 H1B 109.4 . . ?
N1 C1 C17 116.18(17) . . ?
N1 C1 C2 123.20(19) . . ?
C2 C1 C17 120.62(18) . . ?
N1 C5 C6 116.52(17) . . ?
N1 C5 C4 123.27(18) . . ?
C4 C5 C6 120.21(18) . . ?
N5 C17 C1 116.78(18) . . ?
N6 C17 C1 117.82(17) . . ?
N6 C17 N5 125.38(19) . . ?
N2 C6 C5 116.89(19) . . ?
N3 C6 C5 118.14(19) . . ?
N3 C6 N2 125.0(2) . . ?
C18 N5 C17 116.89(19) . . ?
C17 N6 N7 118.07(18) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.9(2) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 C5 118.6(2) . . ?
C3 C4 H4 120.7 . . ?
C7 N2 C6 117.0(2) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2 120.6 . . ?
C19 N7 N6 120.2(2) . . ?
N7 C19 C18 120.0(2) . . ?
N7 C19 C24 113.3(4) . . ?
N7 C19 C24A 116.0(15) . . ?
C18 C19 C24 126.5(4) . . ?
C18 C19 C24A 123.7(15) . . ?
C24A C19 C24 10.0(11) . . ?
C6 N3 N4 117.92(19) . . ?
N5 C18 C19 119.5(2) . . ?
N5 C18 C20 115.6(11) . . ?
N5 C18 C20A 116.0(10) . . ?
C19 C18 C20 124.8(11) . . ?
C19 C18 C20A 124.3(10) . . ?
C20A C18 C20 9.9(16) . . ?
C18 C20 H20 112.2 . . ?
C18 C20 C21 100.0(13) . . ?
C21 C20 H20 112.2 . . ?
C22 C20 C18 120(2) . . ?
C22 C20 H20 112.2 . . ?
C22 C20 C21 98.7(18) . . ?
C19 C24 H24 108.6 . . ?
C26 C24 C19 111.0(7) . . ?
C26 C24 H24 108.6 . . ?
C26 C24 C25 110.3(6) . . ?
C25 C24 C19 109.7(6) . . ?
C25 C24 H24 108.6 . . ?
C8 N4 N3 120.2(2) . . ?
N4 C8 C7 120.0(2) . . ?
N4 C8 C13 115.0(10) . . ?
N4 C8 C13A 114.0(11) . . ?
C7 C8 C13 124.7(10) . . ?
C7 C8 C13A 125.5(11) . . ?
C13A C8 C13 12.6(17) . . ?
N2 C7 C8 119.9(2) . . ?
N2 C7 C9 114.9(3) . . ?
N2 C7 C9A 114.3(4) . . ?
C8 C7 C9 123.6(3) . . ?
C8 C7 C9A 122.6(4) . . ?
C9A C7 C9 30.3(3) . . ?
C8 C13 H13 108.0 . . ?
C14 C13 C8 111.2(17) . . ?
C14 C13 H13 108.0 . . ?
C15 C13 C8 112.8(15) . . ?
C15 C13 H13 108.0 . . ?
C15 C13 C14 108.6(15) . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
C24 C26 C27 110.6(5) . . ?
H26A C26 H26B 108.1 . . ?
C27 C26 H26A 109.5 . . ?
C27 C26 H26B 109.5 . . ?
C7 C9 H9 111.4 . . ?
C7 C9 C10 114.8(6) . . ?
C10 C9 H9 111.4 . . ?
C11 C9 C7 105.7(5) . . ?
C11 C9 H9 111.4 . . ?
C11 C9 C10 101.6(7) . . ?
C20 C22 H22A 112.5 . . ?
C20 C22 H22B 112.5 . . ?
C20 C22 C23 96.3(14) . . ?
H22A C22 H22B 110.0 . . ?
C23 C22 H22A 112.5 . . ?
C23 C22 H22B 112.5 . . ?
C9 C11 H11A 111.1 . . ?
C9 C11 H11B 111.1 . . ?
C12 C11 C9 103.2(8) . . ?
C12 C11 H11A 111.1 . . ?
C12 C11 H11B 111.1 . . ?
H11A C11 H11B 109.1 . . ?
C13 C15 H15A 108.7 . . ?
C13 C15 H15B 108.7 . . ?
C13 C15 C16 114.0(13) . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
H26C C26A H26D 109.0 . . ?
C24A C26A H26C 111.0 . . ?
C24A C26A H26D 111.0 . . ?
C24A C26A C27A 104.0(15) . . ?
C27A C26A H26C 111.0 . . ?
C27A C26A H26D 111.0 . . ?
C19 C24A C26A 110(2) . . ?
C19 C24A H24A 108.1 . . ?
C19 C24A C25A 116(2) . . ?
C26A C24A H24A 108.1 . . ?
C25A C24A C26A 106(2) . . ?
C25A C24A H24A 108.1 . . ?
C26A C27A H27D 109.5 . . ?
C26A C27A H27E 109.5 . . ?
C26A C27A H27F 109.5 . . ?
H27D C27A H27E 109.5 . . ?
H27D C27A H27F 109.5 . . ?
H27E C27A H27F 109.5 . . ?
C24A C25A H25D 109.5 . . ?
C24A C25A H25E 109.5 . . ?
C24A C25A H25F 109.5 . . ?
H25D C25A H25E 109.5 . . ?
H25D C25A H25F 109.5 . . ?
H25E C25A H25F 109.5 . . ?
H21D C21A H21E 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?
C20A C21A H21D 109.5 . . ?
C20A C21A H21E 109.5 . . ?
C20A C21A H21F 109.5 . . ?
C18 C20A C21A 102.2(15) . . ?
C18 C20A H20A 111.1 . . ?
C21A C20A H20A 111.1 . . ?
C22A C20A C18 122(2) . . ?
C22A C20A C21A 97.5(16) . . ?
C22A C20A H20A 111.1 . . ?
C20A C22A H22C 112.9 . . ?
C20A C22A H22D 112.9 . . ?
C20A C22A C23A 94.3(13) . . ?
H22C C22A H22D 110.3 . . ?
C23A C22A H22C 112.9 . . ?
C23A C22A H22D 112.9 . . ?
C22A C23A H23D 109.5 . . ?
C22A C23A H23E 109.5 . . ?
C22A C23A H23F 109.5 . . ?
H23D C23A H23E 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
H11C C11A H11D 110.0 . . ?
C9A C11A H11C 112.5 . . ?
C9A C11A H11D 112.5 . . ?
C9A C11A C12A 96.5(8) . . ?
C12A C11A H11C 112.5 . . ?
C12A C11A H11D 112.5 . . ?
C7 C9A H9A 110.9 . . ?
C7 C9A C10A 115.3(8) . . ?
C11A C9A C7 104.9(8) . . ?
C11A C9A H9A 110.9 . . ?
C11A C9A C10A 103.5(10) . . ?
C10A C9A H9A 110.9 . . ?
C9A C10A H10D 109.5 . . ?
C9A C10A H10E 109.5 . . ?
C9A C10A H10F 109.5 . . ?
H10D C10A H10E 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
C11A C12A H12D 109.5 . . ?
C11A C12A H12E 109.5 . . ?
C11A C12A H12F 109.5 . . ?
H12D C12A H12E 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
C8 C13A H13A 108.3 . . ?
C8 C13A C15A 112.3(18) . . ?
C8 C13A C14A 114.4(17) . . ?
C15A C13A H13A 108.3 . . ?
C14A C13A H13A 108.3 . . ?
C14A C13A C15A 105.0(15) . . ?
C13A C15A H15C 109.4 . . ?
C13A C15A H15D 109.4 . . ?
C13A C15A C16A 111.0(13) . . ?
H15C C15A H15D 108.0 . . ?
C16A C15A H15C 109.4 . . ?
C16A C15A H15D 109.4 . . ?
C13A C14A H14D 109.5 . . ?
C13A C14A H14E 109.5 . . ?
C13A C14A H14F 109.5 . . ?
H14D C14A H14E 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
C15A C16A H16D 109.5 . . ?
C15A C16A H16E 109.5 . . ?
C15A C16A H16F 109.5 . . ?
H16D C16A H16E 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 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
N1 C1 C17 N5 172.33(19) . . . . ?
N1 C1 C17 N6 -9.3(3) . . . . ?
N1 C1 C2 C3 1.1(3) . . . . ?
N1 C5 C6 N2 174.3(2) . . . . ?
N1 C5 C6 N3 -5.5(3) . . . . ?
N1 C5 C4 C3 0.6(3) . . . . ?
C1 N1 C5 C6 179.64(18) . . . . ?
C1 N1 C5 C4 -0.5(3) . . . . ?
C1 C17 N5 C18 -179.9(2) . . . . ?
C1 C17 N6 N7 -179.7(2) . . . . ?
C5 N1 C1 C17 179.46(17) . . . . ?
C5 N1 C1 C2 -0.4(3) . . . . ?
C5 C6 N2 C7 -179.7(3) . . . . ?
C5 C6 N3 N4 179.1(3) . . . . ?
C17 C1 C2 C3 -178.7(2) . . . . ?
C17 N5 C18 C19 -0.8(4) . . . . ?
C17 N5 C18 C20 -176.0(10) . . . . ?
C17 N5 C18 C20A 173.1(10) . . . . ?
C17 N6 N7 C19 -0.2(4) . . . . ?
C6 C5 C4 C3 -179.6(2) . . . . ?
C6 N2 C7 C8 1.0(5) . . . . ?
C6 N2 C7 C9 167.0(4) . . . . ?
C6 N2 C7 C9A -159.6(5) . . . . ?
C6 N3 N4 C8 0.2(5) . . . . ?
N5 C17 N6 N7 -1.5(4) . . . . ?
N5 C18 C20 C21 -78.1(14) . . . . ?
N5 C18 C20 C22 28(2) . . . . ?
N5 C18 C20A C21A 66.0(13) . . . . ?
N5 C18 C20A C22A -41(2) . . . . ?
N6 C17 N5 C18 1.9(4) . . . . ?
N6 N7 C19 C18 1.2(4) . . . . ?
N6 N7 C19 C24 176.8(4) . . . . ?
N6 N7 C19 C24A -172.7(10) . . . . ?
C4 C5 C6 N2 -5.5(3) . . . . ?
C4 C5 C6 N3 174.6(2) . . . . ?
C4 C3 C2 C1 -1.0(4) . . . . ?
N2 C6 N3 N4 -0.8(4) . . . . ?
N2 C7 C9 C10 -52.1(8) . . . . ?
N2 C7 C9 C11 59.0(7) . . . . ?
N2 C7 C9A C11A -53.8(9) . . . . ?
N2 C7 C9A C10A 59.4(10) . . . . ?
C2 C1 C17 N5 -7.9(3) . . . . ?
C2 C1 C17 N6 170.5(2) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
N7 C19 C18 N5 -0.7(4) . . . . ?
N7 C19 C18 C20 174.0(11) . . . . ?
N7 C19 C18 C20A -174.1(10) . . . . ?
N7 C19 C24 C26 46.8(7) . . . . ?
N7 C19 C24 C25 -75.5(7) . . . . ?
N7 C19 C24A C26A -53(2) . . . . ?
N7 C19 C24A C25A 68(2) . . . . ?
C19 C18 C20 C21 107.0(13) . . . . ?
C19 C18 C20 C22 -146.8(17) . . . . ?
C19 C18 C20A C21A -120.4(11) . . . . ?
C19 C18 C20A C22A 132.5(18) . . . . ?
C19 C24 C26 C27 60.4(8) . . . . ?
N3 C6 N2 C7 0.2(4) . . . . ?
N3 N4 C8 C7 0.9(6) . . . . ?
N3 N4 C8 C13 -173.4(10) . . . . ?
N3 N4 C8 C13A 172.9(11) . . . . ?
C18 C19 C24 C26 -138.1(5) . . . . ?
C18 C19 C24 C25 99.7(7) . . . . ?
C18 C19 C24A C26A 133.5(17) . . . . ?
C18 C19 C24A C25A -106(3) . . . . ?
C18 C20 C22 C23 77(2) . . . . ?
C18 C20A C22A C23A -75(2) . . . . ?
C20 C18 C20A C21A -24(11) . . . . ?
C20 C18 C20A C22A -131(13) . . . . ?
C24 C19 C18 N5 -175.6(4) . . . . ?
C24 C19 C18 C20 -0.9(12) . . . . ?
C24 C19 C18 C20A 11.1(12) . . . . ?
C24 C19 C24A C26A 24(9) . . . . ?
C24 C19 C24A C25A 144(13) . . . . ?
N4 C8 C7 N2 -1.5(6) . . . . ?
N4 C8 C7 C9 -166.3(5) . . . . ?
N4 C8 C7 C9A 157.4(6) . . . . ?
N4 C8 C13 C14 63.4(16) . . . . ?
N4 C8 C13 C15 -58.9(19) . . . . ?
N4 C8 C13A C15A 58.7(17) . . . . ?
N4 C8 C13A C14A -60.8(18) . . . . ?
C8 C7 C9 C10 113.4(7) . . . . ?
C8 C7 C9 C11 -135.5(5) . . . . ?
C8 C7 C9A C11A 146.2(6) . . . . ?
C8 C7 C9A C10A -100.5(9) . . . . ?
C8 C13 C15 C16 -43.9(19) . . . . ?
C8 C13A C15A C16A 51.7(17) . . . . ?
C7 C8 C13 C14 -110.5(14) . . . . ?
C7 C8 C13 C15 127.1(14) . . . . ?
C7 C8 C13A C15A -129.9(13) . . . . ?
C7 C8 C13A C14A 110.6(16) . . . . ?
C7 C9 C11 C12 61.7(7) . . . . ?
C13 C8 C7 N2 172.2(11) . . . . ?
C13 C8 C7 C9 7.4(13) . . . . ?
C13 C8 C7 C9A -28.9(13) . . . . ?
C13 C8 C13A C15A -39(8) . . . . ?
C13 C8 C13A C14A -158(10) . . . . ?
C21 C20 C22 C23 -176.4(11) . . . . ?
C9 C7 C9A C11A 44.4(9) . . . . ?
C9 C7 C9A C10A 157.6(16) . . . . ?
C25 C24 C26 C27 -177.7(6) . . . . ?
C10 C9 C11 C12 -178.2(7) . . . . ?
C14 C13 C15 C16 -167.7(15) . . . . ?
C24A C19 C18 N5 172.7(12) . . . . ?
C24A C19 C18 C20 -12.6(16) . . . . ?
C24A C19 C18 C20A -0.6(16) . . . . ?
C24A C19 C24 C26 -61(11) . . . . ?
C24A C19 C24 C25 177(11) . . . . ?
C27A C26A C24A C19 -61(2) . . . . ?
C27A C26A C24A C25A 172(2) . . . . ?
C21A C20A C22A C23A 175.6(11) . . . . ?
C20A C18 C20 C21 16(11) . . . . ?
C20A C18 C20 C22 123(13) . . . . ?
C9A C7 C9 C10 -148.1(14) . . . . ?
C9A C7 C9 C11 -37.0(9) . . . . ?
C12A C11A C9A C7 -61.8(9) . . . . ?
C12A C11A C9A C10A 176.9(9) . . . . ?
C13A C8 C7 N2 -172.5(12) . . . . ?
C13A C8 C7 C9 22.7(14) . . . . ?
C13A C8 C7 C9A -13.6(14) . . . . ?
C13A C8 C13 C14 152(10) . . . . ?
C13A C8 C13 C15 29(8) . . . . ?
C14A C13A C15A C16A 176.6(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/Ethanol'
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# 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_141023_c1_btp
_database_code_depnum_ccdc_archive 'CCDC 1429209'
_audit_update_record             
;
2015-10-02 deposited with the CCDC.	2019-05-07 downloaded from the CCDC.
;
_audit_creation_date             2014-10-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        c1-BTP
_chemical_formula_moiety         'C15 H15 N7, 6(H2 O)'
_chemical_formula_sum            'C15 H27 N7 O6'
_chemical_formula_weight         401.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   15.3819(15)
_cell_length_b                   6.8739(5)
_cell_length_c                   20.2230(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.817(9)
_cell_angle_gamma                90.00
_cell_volume                     2076.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1697
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4637
_cell_measurement_theta_min      3.0788
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.26
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7862
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.14
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0362899000
_diffrn_orient_matrix_UB_12      -0.0089901000
_diffrn_orient_matrix_UB_13      0.0158217000
_diffrn_orient_matrix_UB_21      -0.0037930000
_diffrn_orient_matrix_UB_22      0.1027553000
_diffrn_orient_matrix_UB_23      0.0007244000
_diffrn_orient_matrix_UB_31      -0.0304156000
_diffrn_orient_matrix_UB_32      -0.0020502000
_diffrn_orient_matrix_UB_33      -0.0324598000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2507
_reflns_number_total             3795
_reflns_odcompleteness_completeness 99.50
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         3795
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0537
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0683P)²+0.1885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1525
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O1-H1B
 0.86 with sigma of 0.02
 H1A-O1
 0.86 with sigma of 0.02
 H2A-O2
 0.86 with sigma of 0.02
 O3-H3B
 0.86 with sigma of 0.02
 O2-H2B
 0.86 with sigma of 0.02
 H3A-O3
 0.86 with sigma of 0.02
 O4-H4B
 0.86 with sigma of 0.02
 O4-H4A
 0.86 with sigma of 0.02
 H5B-O5
 0.86 with sigma of 0.02
 O5-H5A
 0.86 with sigma of 0.02
 O6-H6A
 0.86 with sigma of 0.02
 H6B-O6
 0.86 with sigma of 0.02
 H4B-O4
 0.86 with sigma of 0.02
3.a Free rotating group:
 O1(H1A), O5(H5A), O2(H2A,H2B), O3(H3A)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
N1 N 0.61843(12) 0.0410(2) 0.24094(8) 0.0429(4) Uani 1 d . . .
N2 N 0.64579(13) 0.1021(3) 0.35960(8) 0.0508(5) Uani 1 d . . .
N3 N 0.73457(14) 0.1116(3) 0.36404(9) 0.0561(5) Uani 1 d . . .
N4 N 0.43767(12) 0.0721(2) 0.23697(7) 0.0381(4) Uani 1 d . . .
N5 N 0.32011(12) 0.1385(2) 0.11352(8) 0.0444(4) Uani 1 d . . .
N6 N 0.14064(14) 0.1118(3) 0.10702(10) 0.0624(6) Uani 1 d . . .
N7 N 0.20099(13) 0.0789(3) 0.16634(9) 0.0560(5) Uani 1 d . . .
C1 C 0.76549(16) 0.0867(3) 0.30904(12) 0.0512(6) Uani 1 d . . .
C2 C 0.70553(15) 0.0524(3) 0.24536(11) 0.0459(5) Uani 1 d . . .
C3 C 0.59163(15) 0.0658(3) 0.29932(10) 0.0398(5) Uani 1 d . . .
C4 C 0.49518(14) 0.0522(3) 0.29779(9) 0.0384(5) Uani 1 d . . .
C5 C 0.46738(16) 0.0208(3) 0.35749(10) 0.0477(5) Uani 1 d . . .
H5 H 0.5091 0.0075 0.3989 0.057 Uiso 1 calc . . R
C6 C 0.37759(16) 0.0099(3) 0.35419(10) 0.0512(6) Uani 1 d . . .
H6 H 0.3575 -0.0123 0.3934 0.061 Uiso 1 calc . . R
C7 C 0.31722(15) 0.0320(3) 0.29245(10) 0.0462(5) Uani 1 d . . .
H7 H 0.2559 0.0259 0.2892 0.055 Uiso 1 calc . . R
C8 C 0.35006(14) 0.0635(3) 0.23515(9) 0.0382(5) Uani 1 d . . .
C9 C 0.28686(15) 0.0945(3) 0.16757(10) 0.0405(5) Uani 1 d . . .
C10 C 0.26090(17) 0.1741(3) 0.05545(10) 0.0491(6) Uani 1 d . . .
C11 C 0.16858(17) 0.1601(3) 0.05270(11) 0.0573(6) Uani 1 d . . .
C12 C 0.73749(18) 0.0263(4) 0.18196(12) 0.0640(7) Uani 1 d . . .
H12A H 0.6871 0.0068 0.1441 0.096 Uiso 1 calc . . GR
H12B H 0.7763 -0.0848 0.1868 0.096 Uiso 1 calc . . GR
H12C H 0.7697 0.1403 0.1741 0.096 Uiso 1 calc . . GR
C13 C 0.86437(18) 0.0986(4) 0.31758(15) 0.0741(8) Uani 1 d . . .
H13A H 0.8781 0.2031 0.2903 0.111 Uiso 1 calc . . GR
H13B H 0.8859 -0.0217 0.3034 0.111 Uiso 1 calc . . GR
H13C H 0.8927 0.1220 0.3646 0.111 Uiso 1 calc . . GR
C14 C 0.2956(2) 0.2288(4) -0.00475(11) 0.0688(7) Uani 1 d . . .
H14A H 0.3589 0.2058 0.0051 0.103 Uiso 1 calc . . GR
H14B H 0.2838 0.3641 -0.0149 0.103 Uiso 1 calc . . GR
H14C H 0.2663 0.1518 -0.0432 0.103 Uiso 1 calc . . GR
C15 C 0.0976(2) 0.1988(5) -0.01114(14) 0.0973(10) Uani 1 d . . .
H15A H 0.1050 0.1106 -0.0462 0.146 Uiso 1 calc . . GR
H15B H 0.1029 0.3302 -0.0257 0.146 Uiso 1 calc . . GR
H15C H 0.0396 0.1803 -0.0023 0.146 Uiso 1 calc . . GR
O1 O 0.49923(13) 0.0312(3) 0.10382(7) 0.0607(5) Uani 1 d . . D
H1A H 0.5352 0.0206 0.1428 0.091 Uiso 1 d . . DG
H1B H 0.4510(17) 0.075(5) 0.1118(18) 0.115(13) Uiso 1 d . . D
O4 O 0.8774(2) 0.3766(4) 0.12324(15) 0.1120(9) Uani 1 d . . D
H4A H 0.842(2) 0.349(5) 0.0848(12) 0.108(12) Uiso 1 d . . D
H4B H 0.9174(12) 0.380(3) 0.1002(10) 0.026(6) Uiso 1 d . . D
O5 O -0.00806(13) 0.0683(3) 0.17259(9) 0.0691(5) Uani 1 d . . D
H5A H 0.0144 0.1021 0.2135 0.104 Uiso 1 d . . DG
H5B H 0.0268(19) 0.069(5) 0.1452(14) 0.098(11) Uiso 1 d . . D
O2 O 0.42725(15) -0.2283(3) -0.00647(8) 0.0775(6) Uani 1 d . . D
H2A H 0.4491 -0.1670 0.0302 0.116 Uiso 1 d . . DG
H2B H 0.4458 -0.1771 -0.0389 0.116 Uiso 1 d . . DG
O3 O 0.24562(19) -0.2650(3) -0.00802(9) 0.0879(7) Uani 1 d . . D
H3A H 0.2346 -0.2986 0.0296 0.132 Uiso 1 d . . DG
H3B H 0.3039(14) -0.277(6) -0.0070(18) 0.123(15) Uiso 1 d . . D
O6 O 0.08137(15) 0.2069(3) 0.30205(11) 0.0759(5) Uani 1 d . . D
H6A H 0.056(3) 0.312(4) 0.312(2) 0.148(17) Uiso 1 d . . D
H6B H 0.087(3) 0.107(4) 0.3251(18) 0.140(17) Uiso 1 d . . 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
N1 C2 1.324(3) . ?
N1 C3 1.351(2) . ?
N2 N3 1.349(3) . ?
N2 C3 1.326(3) . ?
N3 C1 1.321(3) . ?
N4 C4 1.340(3) . ?
N4 C8 1.341(3) . ?
N5 C9 1.347(2) . ?
N5 C10 1.326(3) . ?
N6 N7 1.349(3) . ?
N6 C11 1.314(3) . ?
N7 C9 1.319(3) . ?
C1 C2 1.413(3) . ?
C1 C13 1.492(3) . ?
C2 C12 1.490(3) . ?
C3 C4 1.479(3) . ?
C4 C5 1.391(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.369(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.375(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.387(3) . ?
C8 C9 1.491(3) . ?
C10 C11 1.411(3) . ?
C10 C14 1.489(3) . ?
C11 C15 1.502(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O1 H1A 0.8506 . ?
O1 H1B 0.851(18) . ?
O4 H4A 0.856(18) . ?
O4 H4B 0.855(11) . ?
O5 H5A 0.8497 . ?
O5 H5B 0.858(18) . ?
O2 H2A 0.8498 . ?
O2 H2B 0.8502 . ?
O3 H3A 0.8501 . ?
O3 H3B 0.896(18) . ?
O6 H6A 0.864(19) . ?
O6 H6B 0.823(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C3 116.66(18) . . ?
C3 N2 N3 118.32(18) . . ?
C1 N3 N2 120.00(19) . . ?
C4 N4 C8 117.37(16) . . ?
C10 N5 C9 116.52(19) . . ?
C11 N6 N7 119.5(2) . . ?
C9 N7 N6 118.44(18) . . ?
N3 C1 C2 120.1(2) . . ?
N3 C1 C13 117.2(2) . . ?
C2 C1 C13 122.7(2) . . ?
N1 C2 C1 120.07(19) . . ?
N1 C2 C12 118.1(2) . . ?
C1 C2 C12 121.8(2) . . ?
N1 C3 C4 119.18(18) . . ?
N2 C3 N1 124.9(2) . . ?
N2 C3 C4 115.97(17) . . ?
N4 C4 C3 116.86(16) . . ?
N4 C4 C5 122.7(2) . . ?
C5 C4 C3 120.42(18) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.8(2) . . ?
C6 C5 H5 120.6 . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.54(19) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7 120.8 . . ?
C6 C7 C8 118.3(2) . . ?
C8 C7 H7 120.8 . . ?
N4 C8 C7 123.24(19) . . ?
N4 C8 C9 116.73(16) . . ?
C7 C8 C9 120.01(19) . . ?
N5 C9 C8 119.01(19) . . ?
N7 C9 N5 125.1(2) . . ?
N7 C9 C8 115.86(17) . . ?
N5 C10 C11 119.62(19) . . ?
N5 C10 C14 117.8(2) . . ?
C11 C10 C14 122.6(2) . . ?
N6 C11 C10 120.8(2) . . ?
N6 C11 C15 116.6(2) . . ?
C10 C11 C15 122.7(2) . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 C13 H13A 109.5 . . ?
C1 C13 H13B 109.5 . . ?
C1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H1A O1 H1B 105.0 . . ?
H4A O4 H4B 84(3) . . ?
H5A O5 H5B 117.1 . . ?
H2A O2 H2B 109.4 . . ?
H3A O3 H3B 111.5 . . ?
H6A O6 H6B 123(4) . . ?

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
N1 C3 C4 N4 -18.8(2) . . . . ?
N1 C3 C4 C5 161.40(18) . . . . ?
N2 N3 C1 C2 0.8(3) . . . . ?
N2 N3 C1 C13 -179.84(19) . . . . ?
N2 C3 C4 N4 161.27(17) . . . . ?
N2 C3 C4 C5 -18.5(3) . . . . ?
N3 N2 C3 N1 -1.4(3) . . . . ?
N3 N2 C3 C4 178.57(16) . . . . ?
N3 C1 C2 N1 -1.4(3) . . . . ?
N3 C1 C2 C12 179.1(2) . . . . ?
N4 C4 C5 C6 -0.1(3) . . . . ?
N4 C8 C9 N5 -3.3(3) . . . . ?
N4 C8 C9 N7 177.75(17) . . . . ?
N5 C10 C11 N6 -0.1(3) . . . . ?
N5 C10 C11 C15 179.8(2) . . . . ?
N6 N7 C9 N5 -1.0(3) . . . . ?
N6 N7 C9 C8 177.82(18) . . . . ?
N7 N6 C11 C10 1.2(3) . . . . ?
N7 N6 C11 C15 -178.7(2) . . . . ?
C2 N1 C3 N2 0.7(3) . . . . ?
C2 N1 C3 C4 -179.24(16) . . . . ?
C3 N1 C2 C1 0.7(3) . . . . ?
C3 N1 C2 C12 -179.83(18) . . . . ?
C3 N2 N3 C1 0.6(3) . . . . ?
C3 C4 C5 C6 179.73(18) . . . . ?
C4 N4 C8 C7 -1.2(3) . . . . ?
C4 N4 C8 C9 177.42(16) . . . . ?
C4 C5 C6 C7 -0.6(3) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C6 C7 C8 N4 0.5(3) . . . . ?
C6 C7 C8 C9 -178.05(18) . . . . ?
C7 C8 C9 N5 175.35(17) . . . . ?
C7 C8 C9 N7 -3.6(3) . . . . ?
C8 N4 C4 C3 -178.84(16) . . . . ?
C8 N4 C4 C5 1.0(3) . . . . ?
C9 N5 C10 C11 -1.5(3) . . . . ?
C9 N5 C10 C14 178.27(18) . . . . ?
C10 N5 C9 N7 2.1(3) . . . . ?
C10 N5 C9 C8 -176.71(17) . . . . ?
C11 N6 N7 C9 -0.7(3) . . . . ?
C13 C1 C2 N1 179.2(2) . . . . ?
C13 C1 C2 C12 -0.2(3) . . . . ?
C14 C10 C11 N6 -179.8(2) . . . . ?
C14 C10 C11 C15 0.1(4) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/Ethanol'
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# 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_150331_ipr_btp
_database_code_depnum_ccdc_archive 'CCDC 1429207'
_audit_update_record             
;
2015-10-02 deposited with the CCDC.	2019-05-07 downloaded from the CCDC.
;
_audit_creation_date             2015-03-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        ipr-BTP
_chemical_formula_moiety         'C23 H31 N7, H2 O'
_chemical_formula_sum            'C23 H33 N7 O'
_chemical_formula_weight         423.56
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   16.0776(13)
_cell_length_b                   8.4467(5)
_cell_length_c                   17.6595(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.910(7)
_cell_angle_gamma                90.00
_cell_volume                     2354.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2015
_cell_measurement_temperature    170
_cell_measurement_theta_max      29.5811
_cell_measurement_theta_min      3.5097
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.28
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10320
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.52
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0095992000
_diffrn_orient_matrix_UB_12      -0.0814144000
_diffrn_orient_matrix_UB_13      0.0063442000
_diffrn_orient_matrix_UB_21      -0.0348730000
_diffrn_orient_matrix_UB_22      -0.0201442000
_diffrn_orient_matrix_UB_23      -0.0293658000
_diffrn_orient_matrix_UB_31      0.0266739000
_diffrn_orient_matrix_UB_32      0.0027419000
_diffrn_orient_matrix_UB_33      -0.0277629000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2830
_reflns_number_total             4286
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0565
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0667P)²+0.7038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1375
_refine_ls_wR_factor_ref         0.1615
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O1(H1A,H1B)
2.b Ternary CH refined with riding coordinates:
 C9(H9), C12(H12), C18(H18), C21(H21)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C23(H23A,
 H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
N1 N 0.45797(11) 0.3849(2) 0.09758(9) 0.0358(4) Uani 1 d . . .
N2 N 0.67305(11) 0.3292(2) 0.07182(10) 0.0388(5) Uani 1 d . . .
N3 N 0.61585(11) 0.5126(2) 0.14979(10) 0.0414(5) Uani 1 d . . .
N4 N 0.69414(12) 0.5662(2) 0.17859(11) 0.0436(5) Uani 1 d . . .
N5 N 0.23434(12) 0.3100(2) 0.08217(11) 0.0428(5) Uani 1 d . . .
N6 N 0.32484(12) 0.4891(2) 0.16151(11) 0.0459(5) Uani 1 d . . .
N7 N 0.26228(12) 0.5235(2) 0.19980(11) 0.0486(5) Uani 1 d . . .
C1 C 0.37984(13) 0.3322(2) 0.06728(12) 0.0360(5) Uani 1 d . . .
C2 C 0.36382(15) 0.2328(3) 0.00353(13) 0.0458(6) Uani 1 d . . .
H2 H 0.3080 0.1961 -0.0160 0.055 Uiso 1 calc . . R
C3 C 0.42986(16) 0.1886(3) -0.03069(14) 0.0533(7) Uani 1 d . . .
H3 H 0.4202 0.1215 -0.0747 0.064 Uiso 1 calc . . R
C4 C 0.51043(15) 0.2419(3) -0.00101(13) 0.0456(6) Uani 1 d . . .
H4 H 0.5570 0.2128 -0.0241 0.055 Uiso 1 calc . . R
C5 C 0.52184(13) 0.3393(2) 0.06353(11) 0.0354(5) Uani 1 d . . .
C6 C 0.60813(14) 0.3979(2) 0.09737(12) 0.0351(5) Uani 1 d . . .
C7 C 0.75029(14) 0.3799(2) 0.10102(12) 0.0363(5) Uani 1 d . . .
C8 C 0.76111(14) 0.5030(3) 0.15562(11) 0.0357(5) Uani 1 d . . .
C9 C 0.82213(15) 0.2955(3) 0.07392(15) 0.0500(6) Uani 1 d . . .
H9 H 0.8729 0.3663 0.0831 0.060 Uiso 1 calc . . R
C10 C 0.8434(3) 0.1474(5) 0.12007(19) 0.1074(15) Uani 1 d . . .
H10A H 0.8592 0.1744 0.1749 0.161 Uiso 1 calc . . GR
H10B H 0.8909 0.0938 0.1034 0.161 Uiso 1 calc . . GR
H10C H 0.7940 0.0771 0.1121 0.161 Uiso 1 calc . . GR
C11 C 0.8011(2) 0.2567(4) -0.01059(16) 0.0840(11) Uani 1 d . . .
H11A H 0.7553 0.1785 -0.0198 0.126 Uiso 1 calc . . GR
H11B H 0.8513 0.2131 -0.0271 0.126 Uiso 1 calc . . GR
H11C H 0.7830 0.3531 -0.0400 0.126 Uiso 1 calc . . GR
C12 C 0.84588(14) 0.5719(3) 0.19354(13) 0.0419(6) Uani 1 d . . .
H12 H 0.8897 0.5334 0.1646 0.050 Uiso 1 calc . . R
C13 C 0.86998(18) 0.5138(4) 0.27670(15) 0.0683(8) Uani 1 d . . .
H13A H 0.8282 0.5516 0.3063 0.102 Uiso 1 calc . . GR
H13B H 0.9261 0.5547 0.2998 0.102 Uiso 1 calc . . GR
H13C H 0.8712 0.3978 0.2773 0.102 Uiso 1 calc . . GR
C14 C 0.84449(18) 0.7518(3) 0.19018(18) 0.0653(8) Uani 1 d . . .
H14A H 0.8284 0.7862 0.1364 0.098 Uiso 1 calc . . GR
H14B H 0.9009 0.7929 0.2121 0.098 Uiso 1 calc . . GR
H14C H 0.8033 0.7922 0.2199 0.098 Uiso 1 calc . . GR
C15 C 0.30953(13) 0.3806(2) 0.10619(12) 0.0362(5) Uani 1 d . . .
C16 C 0.17199(14) 0.3447(3) 0.11948(13) 0.0401(5) Uani 1 d . . .
C17 C 0.18751(14) 0.4507(3) 0.18176(13) 0.0403(5) Uani 1 d . . .
C18 C 0.08795(15) 0.2648(3) 0.09060(15) 0.0510(6) Uani 1 d . . .
H18 H 0.0437 0.3173 0.1148 0.061 Uiso 1 calc . . R
C19 C 0.0929(2) 0.0947(4) 0.1131(2) 0.0936(12) Uani 1 d . . .
H19A H 0.1380 0.0430 0.0918 0.140 Uiso 1 calc . . GR
H19B H 0.0387 0.0430 0.0929 0.140 Uiso 1 calc . . GR
H19C H 0.1053 0.0861 0.1695 0.140 Uiso 1 calc . . GR
C20 C 0.0625(3) 0.2786(7) 0.0040(2) 0.144(2) Uani 1 d . . .
H20A H 0.0543 0.3903 -0.0103 0.216 Uiso 1 calc . . GR
H20B H 0.0096 0.2205 -0.0135 0.216 Uiso 1 calc . . GR
H20C H 0.1072 0.2338 -0.0203 0.216 Uiso 1 calc . . GR
C21 C 0.12415(15) 0.4948(3) 0.23126(13) 0.0484(6) Uani 1 d . . .
H21 H 0.0738 0.4240 0.2170 0.058 Uiso 1 calc . . R
C22 C 0.16055(18) 0.4704(3) 0.31629(15) 0.0614(7) Uani 1 d . . .
H22A H 0.1793 0.3604 0.3250 0.092 Uiso 1 calc . . GR
H22B H 0.1170 0.4934 0.3467 0.092 Uiso 1 calc . . GR
H22C H 0.2089 0.5416 0.3320 0.092 Uiso 1 calc . . GR
C23 C 0.09491(18) 0.6649(4) 0.21431(16) 0.0681(8) Uani 1 d . . .
H23A H 0.1441 0.7358 0.2238 0.102 Uiso 1 calc . . GR
H23B H 0.0555 0.6947 0.2480 0.102 Uiso 1 calc . . GR
H23C H 0.0664 0.6738 0.1603 0.102 Uiso 1 calc . . GR
O1 O 0.48393(13) 0.6811(3) 0.21194(16) 0.0978(9) Uani 1 d . . .
H1A H 0.5239 0.6362 0.1948 0.147 Uiso 1 d . . G
H1B H 0.4382 0.6299 0.1972 0.147 Uiso 1 d . . G


_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
N1 C1 1.345(3) . ?
N1 C5 1.341(3) . ?
N2 C6 1.345(3) . ?
N2 C7 1.322(3) . ?
N3 N4 1.344(2) . ?
N3 C6 1.329(3) . ?
N4 C8 1.332(3) . ?
N5 C15 1.343(3) . ?
N5 C16 1.332(3) . ?
N6 N7 1.346(3) . ?
N6 C15 1.328(3) . ?
N7 C17 1.334(3) . ?
C1 C2 1.389(3) . ?
C1 C15 1.487(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.369(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.378(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(3) . ?
C5 C6 1.488(3) . ?
C7 C8 1.406(3) . ?
C7 C9 1.510(3) . ?
C8 C12 1.516(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.497(4) . ?
C9 C11 1.503(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12 1.0000 . ?
C12 C13 1.527(3) . ?
C12 C14 1.521(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 C17 1.403(3) . ?
C16 C18 1.510(3) . ?
C17 C21 1.509(3) . ?
C18 H18 1.0000 . ?
C18 C19 1.489(4) . ?
C18 C20 1.511(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21 1.0000 . ?
C21 C22 1.519(3) . ?
C21 C23 1.524(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O1 H1A 0.8501 . ?
O1 H1B 0.8502 . ?

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 117.61(18) . . ?
C7 N2 C6 117.44(18) . . ?
C6 N3 N4 117.82(18) . . ?
C8 N4 N3 120.18(18) . . ?
C16 N5 C15 117.56(19) . . ?
C15 N6 N7 117.81(19) . . ?
C17 N7 N6 120.39(19) . . ?
N1 C1 C2 122.6(2) . . ?
N1 C1 C15 117.38(18) . . ?
C2 C1 C15 120.0(2) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.8(2) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.7(2) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.3(2) . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C4 123.0(2) . . ?
N1 C5 C6 117.34(18) . . ?
C4 C5 C6 119.7(2) . . ?
N2 C6 C5 116.48(19) . . ?
N3 C6 N2 124.9(2) . . ?
N3 C6 C5 118.64(19) . . ?
N2 C7 C8 119.5(2) . . ?
N2 C7 C9 116.20(19) . . ?
C8 C7 C9 124.3(2) . . ?
N4 C8 C7 120.2(2) . . ?
N4 C8 C12 115.00(19) . . ?
C7 C8 C12 124.8(2) . . ?
C7 C9 H9 108.4 . . ?
C10 C9 C7 109.4(2) . . ?
C10 C9 H9 108.4 . . ?
C10 C9 C11 110.1(2) . . ?
C11 C9 C7 112.1(2) . . ?
C11 C9 H9 108.4 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 H12 108.1 . . ?
C8 C12 C13 110.2(2) . . ?
C8 C12 C14 111.15(19) . . ?
C13 C12 H12 108.1 . . ?
C14 C12 H12 108.1 . . ?
C14 C12 C13 111.0(2) . . ?
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 . . ?
N5 C15 C1 116.74(19) . . ?
N6 C15 N5 124.7(2) . . ?
N6 C15 C1 118.56(19) . . ?
N5 C16 C17 119.3(2) . . ?
N5 C16 C18 116.3(2) . . ?
C17 C16 C18 124.4(2) . . ?
N7 C17 C16 120.0(2) . . ?
N7 C17 C21 115.1(2) . . ?
C16 C17 C21 124.9(2) . . ?
C16 C18 H18 108.7 . . ?
C16 C18 C20 111.1(2) . . ?
C19 C18 C16 110.0(2) . . ?
C19 C18 H18 108.7 . . ?
C19 C18 C20 109.6(3) . . ?
C20 C18 H18 108.7 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21 108.0 . . ?
C17 C21 C22 111.3(2) . . ?
C17 C21 C23 109.6(2) . . ?
C22 C21 H21 108.0 . . ?
C22 C21 C23 111.7(2) . . ?
C23 C21 H21 108.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
H1A O1 H1B 109.4 . . ?

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
N1 C1 C2 C3 -1.1(3) . . . . ?
N1 C1 C15 N5 -171.00(18) . . . . ?
N1 C1 C15 N6 9.1(3) . . . . ?
N1 C5 C6 N2 168.31(18) . . . . ?
N1 C5 C6 N3 -11.8(3) . . . . ?
N2 C7 C8 N4 1.0(3) . . . . ?
N2 C7 C8 C12 179.94(19) . . . . ?
N2 C7 C9 C10 -83.0(3) . . . . ?
N2 C7 C9 C11 39.4(3) . . . . ?
N3 N4 C8 C7 0.1(3) . . . . ?
N3 N4 C8 C12 -178.90(18) . . . . ?
N4 N3 C6 N2 1.2(3) . . . . ?
N4 N3 C6 C5 -178.69(18) . . . . ?
N4 C8 C12 C13 73.8(3) . . . . ?
N4 C8 C12 C14 -49.6(3) . . . . ?
N5 C16 C17 N7 4.4(3) . . . . ?
N5 C16 C17 C21 -177.1(2) . . . . ?
N5 C16 C18 C19 73.5(3) . . . . ?
N5 C16 C18 C20 -48.1(4) . . . . ?
N6 N7 C17 C16 -3.9(3) . . . . ?
N6 N7 C17 C21 177.5(2) . . . . ?
N7 N6 C15 N5 4.6(3) . . . . ?
N7 N6 C15 C1 -175.47(19) . . . . ?
N7 C17 C21 C22 -54.6(3) . . . . ?
N7 C17 C21 C23 69.4(3) . . . . ?
C1 N1 C5 C4 0.3(3) . . . . ?
C1 N1 C5 C6 -179.96(18) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C2 C1 C15 N5 7.2(3) . . . . ?
C2 C1 C15 N6 -172.7(2) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 N1 -0.7(3) . . . . ?
C3 C4 C5 C6 179.5(2) . . . . ?
C4 C5 C6 N2 -11.9(3) . . . . ?
C4 C5 C6 N3 168.0(2) . . . . ?
C5 N1 C1 C2 0.6(3) . . . . ?
C5 N1 C1 C15 178.83(18) . . . . ?
C6 N2 C7 C8 -1.0(3) . . . . ?
C6 N2 C7 C9 177.31(18) . . . . ?
C6 N3 N4 C8 -1.2(3) . . . . ?
C7 N2 C6 N3 -0.1(3) . . . . ?
C7 N2 C6 C5 179.82(18) . . . . ?
C7 C8 C12 C13 -105.1(3) . . . . ?
C7 C8 C12 C14 131.5(2) . . . . ?
C8 C7 C9 C10 95.3(3) . . . . ?
C8 C7 C9 C11 -142.3(3) . . . . ?
C9 C7 C8 N4 -177.1(2) . . . . ?
C9 C7 C8 C12 1.8(3) . . . . ?
C15 N5 C16 C17 -0.6(3) . . . . ?
C15 N5 C16 C18 179.38(19) . . . . ?
C15 N6 N7 C17 -0.4(3) . . . . ?
C15 C1 C2 C3 -179.3(2) . . . . ?
C16 N5 C15 N6 -4.0(3) . . . . ?
C16 N5 C15 C1 176.06(19) . . . . ?
C16 C17 C21 C22 126.9(2) . . . . ?
C16 C17 C21 C23 -109.1(3) . . . . ?
C17 C16 C18 C19 -106.5(3) . . . . ?
C17 C16 C18 C20 131.9(3) . . . . ?
C18 C16 C17 N7 -175.5(2) . . . . ?
C18 C16 C17 C21 2.9(4) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/Ethanol'
_chemical_properties_physical    Heat-sensitive
_exptl_crystal_preparation       Luminescent
