# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_ATL-FMA_hyd
_database_code_depnum_ccdc_archive 'CCDC 2227182'
loop_
_audit_author_name
_audit_author_address
'Palash Sanphui'
;SRM Institute of Science and Technology
India
;
_audit_update_record             
;
2022-12-17 deposited with the CCDC.	2024-10-29 downloaded from the CCDC.
;
_audit_creation_date             2022-12-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C14 H23 N2 O3, C2 H O2, H2 O'
_chemical_formula_sum            'C16 H26 N2 O6'
_chemical_formula_weight         342.39
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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

_symmetry_Int_Tables_number      14
_cell_length_a                   11.6451(3)
_cell_length_b                   9.4203(3)
_cell_length_c                   17.2278(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.1970(10)
_cell_angle_gamma                90
_cell_volume                     1805.41(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9869
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      2.48
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6839
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0642 before and 0.0506 after correction.
The Ratio of minimum to maximum transmission is 0.9171.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.2596
_exptl_crystal_description       block
_exptl_crystal_F_000             736.4384
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            38976
_diffrn_reflns_theta_full        28.3521
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.48
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.9951
_diffrn_measured_fraction_theta_max 0.9951
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -15
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                3976
_reflns_number_total             4496
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40E (?, 2016)'
_computing_data_reduction        'SAINT V8.40E (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.6879
_refine_diff_density_min         -0.2259
_refine_diff_density_rms         0.0470
_refine_ls_d_res_high            0.7483
_refine_ls_d_res_low             8.2288
_refine_ls_goodness_of_fit_ref   1.0452
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    37
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4496
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0577
_refine_ls_restrained_S_all      1.0452
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0659P)²+0.9320P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1535
_refine_ls_wR_factor_ref         0.1579
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 N2(H2a,H2b), C2(H2c,H2d), C9(H9a,H9b), C11(H11a,H11b)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C4(H4), C5(H5), C7(H7), C8(H8)
2.d X=CH2 refined with riding coordinates:
 N1(H1a,H1b)
2.e Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C13(H13a,H13b,H13c)
;
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_refinement_flags_posn
O3 O 0.56190(10) 0.84126(14) 0.50027(7) 0.0420(3) Uani 1.000000 .
O1 O 0.08804(17) 0.27603(17) 0.73466(11) 0.0746(5) Uani 1.000000 .
O4 O 0.84565(11) 0.9780(2) 0.57502(7) 0.0616(4) Uani 1.000000 .
O5 O 0.74741(10) 0.90783(15) 0.45076(7) 0.0477(3) Uani 1.000000 .
O6 O 0.28265(18) 0.0966(3) 0.72210(12) 0.0852(6) Uani 1.000000 .
O2 O 0.39784(11) 0.73402(15) 0.57286(10) 0.0565(4) Uani 1.000000 .
N2 N 0.64354(11) 1.04833(16) 0.61630(8) 0.0381(3) Uani 1.000000 .
H2a H 0.71052(11) 1.02673(16) 0.60288(8) 0.0457(4) Uiso 1.000000 R
H2b H 0.58979(11) 1.08365(16) 0.57163(8) 0.0457(4) Uiso 1.000000 R
N1 N 0.01494(15) 0.48364(19) 0.75996(10) 0.0528(4) Uani 1.000000 .
H1a H 0.03469(15) 0.46653(19) 0.81125(10) 0.0634(5) Uiso 1.000000 R
H1b H -0.02000(15) 0.56219(19) 0.74122(10) 0.0634(5) Uiso 1.000000 R
C1 C 0.03827(16) 0.3892(2) 0.70991(11) 0.0465(4) Uani 1.000000 .
C2 C 0.00506(19) 0.4295(3) 0.62139(12) 0.0590(6) Uani 1.000000 .
C3 C 0.10947(15) 0.5071(2) 0.60440(10) 0.0449(4) Uani 1.000000 .
C4 C 0.2039(2) 0.4338(2) 0.59222(14) 0.0608(6) Uani 1.000000 .
C5 C 0.3043(2) 0.5046(2) 0.58172(15) 0.0608(5) Uani 1.000000 .
C6 C 0.30596(15) 0.6513(2) 0.58358(11) 0.0458(4) Uani 1.000000 .
C9 C 0.51560(15) 0.67475(19) 0.59088(11) 0.0440(4) Uani 1.000000 .
C10 C 0.59754(15) 0.7944(2) 0.58258(10) 0.0435(4) Uani 1.000000 .
C11 C 0.59374(17) 0.9150(2) 0.63984(11) 0.0483(4) Uani 1.000000 .
C12 C 0.67393(15) 1.1625(2) 0.68041(11) 0.0468(4) Uani 1.000000 .
C14 C 0.7323(3) 1.2824(3) 0.64871(18) 0.0787(8) Uani 1.000000 .
C7 C 0.21135(17) 0.7246(2) 0.59543(13) 0.0518(4) Uani 1.000000 .
C8 C 0.11418(17) 0.6533(2) 0.60574(12) 0.0518(4) Uani 1.000000 .
C13 C 0.56366(18) 1.2100(3) 0.70214(13) 0.0616(6) Uani 1.000000 .
C15 C 0.84026(13) 0.94968(17) 0.50362(9) 0.0360(3) Uani 1.000000 .
C16 C 0.95093(13) 0.96913(18) 0.47757(10) 0.0375(3) Uani 1.000000 .
H16 H 0.95008(13) 0.93551(18) 0.42665(10) 0.0450(4) Uiso 1.000000 R
H6a H 0.272(3) 0.093(4) 0.672(2) 0.098(11) Uiso 1.000000 .
H6b H 0.225(3) 0.154(4) 0.725(2) 0.112(13) Uiso 1.000000 .
H4 H 0.2017(2) 0.3352(2) 0.59086(14) 0.0730(7) Uiso 1.000000 R
H5 H 0.3683(2) 0.4539(2) 0.57367(15) 0.0729(6) Uiso 1.000000 R
H7 H 0.21283(17) 0.8233(2) 0.59651(13) 0.0621(5) Uiso 1.000000 R
H8 H 0.05038(17) 0.7046(2) 0.61377(12) 0.0621(5) Uiso 1.000000 R
H10 H 0.68004(15) 0.7583(2) 0.59611(10) 0.0522(5) Uiso 1.000000 R
H12 H 0.73201(15) 1.1240(2) 0.72926(11) 0.0562(5) Uiso 1.000000 R
H2c H -0.01402(19) 0.3447(3) 0.58803(12) 0.0708(7) Uiso 1.000000 R
H2d H -0.06539(19) 0.4901(3) 0.60781(12) 0.0708(7) Uiso 1.000000 R
H9a H 0.54072(15) 0.63682(19) 0.64567(11) 0.0528(5) Uiso 1.000000 R
H9b H 0.51714(15) 0.59880(19) 0.55319(11) 0.0528(5) Uiso 1.000000 R
H14a H 0.7985(12) 1.2465(5) 0.6321(12) 0.1181(12) Uiso 1.000000 GR
H14b H 0.6746(6) 1.3254(15) 0.6031(8) 0.1181(12) Uiso 1.000000 GR
H14c H 0.7610(17) 1.3519(11) 0.6907(4) 0.1181(12) Uiso 1.000000 GR
H13a H 0.5055(7) 1.2470(18) 0.6546(3) 0.0924(8) Uiso 1.000000 GR
H13b H 0.5298(9) 1.1307(5) 0.7227(10) 0.0924(8) Uiso 1.000000 GR
H13c H 0.5855(3) 1.2827(14) 0.7429(8) 0.0924(8) Uiso 1.000000 GR
H3 H 0.622(2) 0.868(3) 0.4861(14) 0.063(7) Uiso 1.000000 .
H11a H 0.63976(17) 0.8890(2) 0.69469(11) 0.0580(5) Uiso 1.000000 R
H11b H 0.51124(17) 0.9311(2) 0.63934(11) 0.0580(5) Uiso 1.000000 R


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
O3 C10 1.425(2) . ?
O3 H3 0.85(2) . ?
O1 C1 1.228(2) . ?
O4 C15 1.2420(19) . ?
O5 C15 1.2536(19) . ?
O6 H6a 0.84(4) . ?
O6 H6b 0.87(4) . ?
O2 C6 1.380(2) . ?
O2 C9 1.427(2) . ?
N2 H2a 0.9000 . ?
N2 H2b 0.9000 . ?
N2 C11 1.489(2) . ?
N2 C12 1.507(2) . ?
N1 H1a 0.8600 . ?
N1 H1b 0.8600 . ?
N1 C1 1.322(2) . ?
C1 C2 1.507(3) . ?
C2 C3 1.520(2) . ?
C2 H2c 0.9700 . ?
C2 H2d 0.9700 . ?
C3 C4 1.366(3) . ?
C3 C8 1.379(3) . ?
C4 C5 1.403(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.366(3) . ?
C9 C10 1.511(2) . ?
C9 H9a 0.9700 . ?
C9 H9b 0.9700 . ?
C10 C11 1.514(3) . ?
C10 H10 0.9800 . ?
C11 H11a 0.9700 . ?
C11 H11b 0.9700 . ?
C12 C14 1.502(3) . ?
C12 C13 1.508(2) . ?
C12 H12 0.9800 . ?
C14 H14a 0.9600 . ?
C14 H14b 0.9600 . ?
C14 H14c 0.9600 . ?
C7 C8 1.372(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C13 H13a 0.9600 . ?
C13 H13b 0.9600 . ?
C13 H13c 0.9600 . ?
C15 C16 1.4960(19) . ?
C16 C16 1.311(3) 3_776 ?
C16 H16 0.9300 . ?

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
H3 O3 C10 110.8(16) . . ?
H6b O6 H6a 102(3) . . ?
C9 O2 C6 118.89(14) . . ?
H2b N2 H2a 107.5 . . ?
C11 N2 H2a 108.44(9) . . ?
C11 N2 H2b 108.44(9) . . ?
C12 N2 H2a 108.44(8) . . ?
C12 N2 H2b 108.44(9) . . ?
C12 N2 C11 115.36(13) . . ?
H1b N1 H1a 120.0 . . ?
C1 N1 H1a 120.0 . . ?
C1 N1 H1b 120.0 . . ?
N1 C1 O1 121.65(19) . . ?
C2 C1 O1 121.55(19) . . ?
C2 C1 N1 116.75(19) . . ?
C3 C2 C1 109.59(15) . . ?
H2c C2 C1 109.75(12) . . ?
H2c C2 C3 109.75(11) . . ?
H2d C2 C1 109.75(12) . . ?
H2d C2 C3 109.75(13) . . ?
H2d C2 H2c 108.2 . . ?
C4 C3 C2 120.87(18) . . ?
C8 C3 C2 120.51(19) . . ?
C8 C3 C4 118.51(16) . . ?
C5 C4 C3 121.28(18) . . ?
H4 C4 C3 119.36(11) . . ?
H4 C4 C5 119.36(12) . . ?
C6 C5 C4 118.60(19) . . ?
H5 C5 C4 120.70(12) . . ?
H5 C5 C6 120.70(11) . . ?
C5 C6 O2 124.61(18) . . ?
C7 C6 O2 115.23(17) . . ?
C7 C6 C5 120.16(17) . . ?
C10 C9 O2 106.31(14) . . ?
H9a C9 O2 110.47(9) . . ?
H9a C9 C10 110.47(9) . . ?
H9b C9 O2 110.47(10) . . ?
H9b C9 C10 110.47(10) . . ?
H9b C9 H9a 108.7 . . ?
C9 C10 O3 108.61(14) . . ?
C11 C10 O3 111.08(15) . . ?
C11 C10 C9 110.94(14) . . ?
H10 C10 O3 108.72(8) . . ?
H10 C10 C9 108.72(9) . . ?
H10 C10 C11 108.72(10) . . ?
C10 C11 N2 111.53(13) . . ?
H11a C11 N2 109.32(9) . . ?
H11a C11 C10 109.32(10) . . ?
H11b C11 N2 109.32(9) . . ?
H11b C11 C10 109.32(9) . . ?
H11b C11 H11a 108.0 . . ?
C14 C12 N2 107.68(15) . . ?
C13 C12 N2 111.18(14) . . ?
C13 C12 C14 112.1(2) . . ?
H12 C12 N2 108.59(9) . . ?
H12 C12 C14 108.59(14) . . ?
H12 C12 C13 108.59(11) . . ?
H14a C14 C12 109.5 . . ?
H14b C14 C12 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 C12 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 109.5 . . ?
C8 C7 C6 120.33(18) . . ?
H7 C7 C6 119.83(10) . . ?
H7 C7 C8 119.83(12) . . ?
C7 C8 C3 121.13(19) . . ?
H8 C8 C3 119.44(11) . . ?
H8 C8 C7 119.44(12) . . ?
H13a C13 C12 109.5 . . ?
H13b C13 C12 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 C12 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?
O5 C15 O4 124.55(14) . . ?
C16 C15 O4 118.37(14) . . ?
C16 C15 O5 117.07(13) . . ?
C16 C16 C15 123.74(18) 3_776 . ?
H16 C16 C15 118.13(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_systematic        'Atenolol fumarate hydrate'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone-methanol mixture'
####################################################################### 
# 
# 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_ATL-ADP
_database_code_depnum_ccdc_archive 'CCDC 2291533'
loop_
_audit_author_name
_audit_author_address
'Palash Sanphui'
;SRM Institute of Science and Technology
India
;
_audit_update_record             
;
2024-08-30 deposited with the CCDC.	2024-10-29 downloaded from the CCDC.
;
_audit_creation_date             2024-08-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_chemical_formula_moiety         '4(C14 H23 N2 O3), 2(C6 H8 O4), 4(H2 O)'
_chemical_formula_sum            'C68 H116 N8 O24'
_chemical_formula_weight         1429.719
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   9.6036(8)
_cell_length_b                   17.9226(16)
_cell_length_c                   22.449(2)
_cell_angle_alpha                78.088(3)
_cell_angle_beta                 81.020(3)
_cell_angle_gamma                89.960(3)
_cell_volume                     3732.5(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1020
_cell_measurement_temperature    101.00
_cell_measurement_theta_max      19.47
_cell_measurement_theta_min      2.80
_exptl_absorpt_coefficient_mu    0.096
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       block
_exptl_crystal_F_000             1545.126
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.9996
_diffrn_reflns_Laue_measured_fraction_max 0.9996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            225274
_diffrn_reflns_point_group_measured_fraction_full 0.9996
_diffrn_reflns_point_group_measured_fraction_max 0.9996
_diffrn_reflns_theta_full        24.9998
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.88
_diffrn_ambient_temperature      374.00
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.9996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              21
_reflns_limit_k_min              -20
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                12505
_reflns_number_total             13163
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         1.5739
_refine_diff_density_min         -0.6050
_refine_diff_density_rms         0.1251
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             10.8425
_refine_ls_goodness_of_fit_ref   1.0267
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    181
_refine_ls_number_parameters     930
_refine_ls_number_reflns         13163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.1049
_refine_ls_restrained_S_all      1.0267
_refine_ls_shift/su_max          -0.0160
_refine_ls_shift/su_mean         0.0004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0816P)²+24.0104P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2518
_refine_ls_wR_factor_ref         0.2538
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O24(H24a,H24b), O21(H21a,H21b), O23(H23c,H23d)
2.b Ternary CH refined with riding coordinates:
 C24(H24), C26(H26), C10(H10), C12(H12), C52(H52), C38(H38), C40(H40), C54(H54)
2.c Secondary CH2 refined with riding coordinates:
 N2(H2a,H2b), N4(H4a,H4b), N8(H8a,H8b), N6(H6a,H6b), C25(H25a,H25b), C11(H11a,
 H11b), C37(H37a,H37b), C23(H23a,H23b), C44(H44a,H44b), C16(H16a,H16b), C9(H9a,
 H9b), C51(H51a,H51b), C30(H30a,H30b), C53(H53a,H53b), C2(H2c,H2d), C67(H67a,
 H67b), C61(H61a,H61b), C66(H66a,H66b), C64(H64a,H64b), C39(H39a,H39b),
 C58(H58a,H58b), C65(H65a,H65b), C60(H60a,H60b), C59(H59a,H59b)
2.d Aromatic/amide H refined with riding coordinates:
 C21(H21), C5(H5), C4(H4), C19(H19), C7(H7), C32(H32), C47(H47), C8(H8),
 C46(H46), C22(H22), C18(H18), C50(H50), C35(H35), C49(H49), C33(H33), C36(H36)
2.e X=CH2 refined with riding coordinates:
 N7(H7a,H7b), N3(H3a,H3b), N1(H1a,H1b), N5(H5a,H5b)
2.f Idealised Me refined as rotating group:
 C27(H27a,H27b,H27c), C14(H14a,H14b,H14c), C28(H28a,H28b,H28c), C13(H13a,H13b,
 H13c), C56(H56a,H56b,H56c), C41(H41a,H41b,H41c), C42(H42a,H42b,H42c), C55(H55a,
 H55b,H55c)
2.g Idealised tetrahedral OH refined as rotating group:
 O12(H12a), O9(H9), O3(H3), O6(H6)
;
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_refinement_flags_posn
O2 O 0.3948(3) 0.56821(16) 0.13945(13) 0.0187(6) Uani 1.000000 .
O5 O -0.1184(3) 0.11996(17) 0.13623(13) 0.0212(6) Uani 1.000000 .
O19 O 0.5322(3) 0.10222(17) 0.59862(14) 0.0247(7) Uani 1.000000 .
O15 O 0.8797(3) 0.41875(18) 0.63920(14) 0.0265(7) Uani 1.000000 .
O8 O 1.1200(3) 0.3899(2) 0.85822(14) 0.0268(7) Uani 1.000000 .
O16 O 1.0367(3) 0.34661(18) 0.59861(14) 0.0248(7) Uani 1.000000 .
O20 O 0.3734(3) 0.00958(17) 0.64023(14) 0.0246(7) Uani 1.000000 .
O7 O 0.8875(3) 0.31555(19) 1.16638(15) 0.0280(7) Uani 1.000000 .
O12 O 0.4351(3) 0.03129(19) 0.74581(14) 0.0249(7) Uani 1.000000 .
H12a H 0.428(3) 0.029(3) 0.7095(9) 0.0373(10) Uiso 1.000000 GR
O11 O 0.6426(3) -0.0781(2) 0.84955(14) 0.0304(8) Uani 1.000000 .
O9 O 0.9292(3) 0.34241(19) 0.74526(14) 0.0250(7) Uani 1.000000 .
H9 H 0.9553(12) 0.308(2) 0.727(2) 0.0375(10) Uiso 1.000000 GR
O1 O 0.6120(3) 0.6359(2) -0.16384(15) 0.0297(7) Uani 1.000000 .
O10 O 0.4961(3) -0.1821(2) 1.15917(15) 0.0323(8) Uani 1.000000 .
O17 O -0.0034(4) 0.1489(2) 0.37793(16) 0.0336(8) Uani 1.000000 .
O4 O 0.0092(3) 0.1454(2) -0.16672(16) 0.0325(8) Uani 1.000000 .
O14 O 0.4952(4) 0.4171(2) 0.38130(17) 0.0385(9) Uani 1.000000 .
O3 O 0.5420(3) 0.5189(2) 0.24221(15) 0.0318(8) Uani 1.000000 .
H3 H 0.566(3) 0.509(3) 0.2774(6) 0.0477(12) Uiso 1.000000 GR
O18 O 0.1305(4) 0.0595(2) 0.34775(17) 0.0394(9) Uani 1.000000 .
O6 O 0.0384(4) 0.1189(2) 0.23918(16) 0.0352(8) Uani 1.000000 .
H6 H 0.072(3) 0.102(3) 0.2716(13) 0.0528(12) Uiso 1.000000 GR
N2 N 0.2674(4) 0.4615(2) 0.32486(15) 0.0182(7) Uani 1.000000 .
H2a H 0.3536(4) 0.4474(2) 0.33586(15) 0.0218(9) Uiso 1.000000 R
H2b H 0.2335(4) 0.4975(2) 0.34688(15) 0.0218(9) Uiso 1.000000 R
N4 N -0.2348(4) 0.1319(2) 0.32405(15) 0.0170(7) Uani 1.000000 .
H4a H -0.2659(4) 0.0838(2) 0.34540(15) 0.0204(9) Uiso 1.000000 R
H4b H -0.1486(4) 0.1411(2) 0.33455(15) 0.0204(9) Uiso 1.000000 R
N8 N 0.7267(4) 0.0659(2) 0.67741(17) 0.0219(8) Uani 1.000000 .
H8a H 0.7705(4) 0.0263(2) 0.66262(17) 0.0263(9) Uiso 1.000000 R
H8b H 0.6477(4) 0.0770(2) 0.65909(17) 0.0263(9) Uiso 1.000000 R
N7 N 0.6955(4) -0.1342(2) 1.17805(16) 0.0211(8) Uani 1.000000 .
H7a H 0.7876(4) -0.1277(2) 1.16794(16) 0.0253(9) Uiso 1.000000 R
H7b H 0.6503(4) -0.1148(2) 1.20823(16) 0.0253(9) Uiso 1.000000 R
N3 N -0.1968(4) 0.1987(2) -0.18109(17) 0.0224(8) Uani 1.000000 .
H3a H -0.2888(4) 0.1978(2) -0.16972(17) 0.0269(9) Uiso 1.000000 R
H3b H -0.1556(4) 0.2353(2) -0.21100(17) 0.0269(9) Uiso 1.000000 R
N1 N 0.3893(4) 0.6122(2) -0.17662(18) 0.0269(9) Uani 1.000000 .
H1a H 0.2991(4) 0.6208(2) -0.16734(18) 0.0323(10) Uiso 1.000000 R
H1b H 0.4165(4) 0.5798(2) -0.20035(18) 0.0323(10) Uiso 1.000000 R
N6 N 1.2227(4) 0.3411(2) 0.68265(17) 0.0265(9) Uani 1.000000 .
H6a H 1.2692(4) 0.3876(2) 0.66779(17) 0.0318(10) Uiso 1.000000 R
H6b H 1.1454(4) 0.3401(2) 0.66317(17) 0.0318(10) Uiso 1.000000 R
N5 N 1.1120(4) 0.2853(2) 1.17713(17) 0.0271(9) Uani 1.000000 .
H5a H 1.0857(4) 0.2406(2) 1.20100(17) 0.0325(10) Uiso 1.000000 R
H5b H 1.2019(4) 0.2993(2) 1.16788(17) 0.0325(10) Uiso 1.000000 R
O13 O 0.6317(5) 0.5204(2) 0.3493(2) 0.0505(11) Uani 1.000000 .
C20 C -0.1367(4) 0.1076(2) 0.07961(19) 0.0188(9) Uani 1.000000 .
C6 C 0.4017(4) 0.6059(2) 0.07921(18) 0.0160(8) Uani 1.000000 .
C34 C 1.1021(5) 0.3908(2) 0.92047(19) 0.0194(9) Uani 1.000000 .
C62 C 0.9346(5) 0.3893(2) 0.59523(19) 0.0205(9) Uani 1.000000 .
C45 C 0.6877(4) -0.1674(2) 1.0319(2) 0.0181(8) Uani 1.000000 .
C29 C 1.0144(4) 0.3325(2) 1.15474(18) 0.0187(9) Uani 1.000000 .
C3 C 0.4202(4) 0.6676(2) -0.04635(19) 0.0172(8) Uani 1.000000 .
C1 C 0.4853(5) 0.6486(3) -0.15462(19) 0.0230(9) Uani 1.000000 .
C43 C 0.6245(4) -0.1735(2) 1.14773(19) 0.0197(9) Uani 1.000000 .
C25 C -0.2136(4) 0.1316(2) 0.25684(18) 0.0190(9) Uani 1.000000 .
H25a H -0.1928(4) 0.1842(2) 0.23255(18) 0.0227(10) Uiso 1.000000 R
H25b H -0.3004(4) 0.1121(2) 0.24584(18) 0.0227(10) Uiso 1.000000 R
C31 C 1.0843(5) 0.3989(2) 1.04420(19) 0.0191(9) Uani 1.000000 .
C68 C 0.4284(4) 0.0606(2) 0.59575(19) 0.0193(9) Uani 1.000000 .
C15 C -0.1201(4) 0.1447(3) -0.15306(19) 0.0201(9) Uani 1.000000 .
C11 C 0.2908(4) 0.4985(2) 0.25810(18) 0.0183(8) Uani 1.000000 .
H11a H 0.2041(4) 0.5241(2) 0.24706(18) 0.0220(10) Uiso 1.000000 R
H11b H 0.3125(4) 0.4594(2) 0.23296(18) 0.0220(10) Uiso 1.000000 R
C17 C -0.1753(4) 0.0933(2) -0.03846(19) 0.0192(9) Uani 1.000000 .
C24 C -0.0904(4) 0.0807(3) 0.24187(19) 0.0205(9) Uani 1.000000 .
H24 H -0.0977(4) 0.0343(3) 0.27585(19) 0.0246(11) Uiso 1.000000 R
C26 C -0.3363(5) 0.1884(2) 0.3458(2) 0.0214(9) Uani 1.000000 .
H26 H -0.3460(5) 0.1782(2) 0.3918(2) 0.0257(11) Uiso 1.000000 R
C48 C 0.6489(5) -0.1049(2) 0.91113(19) 0.0217(9) Uani 1.000000 .
C10 C 0.4130(4) 0.5570(2) 0.2446(2) 0.0200(9) Uani 1.000000 .
H10 H 0.4047(4) 0.5859(2) 0.2785(2) 0.0240(10) Uiso 1.000000 R
C37 C 1.0023(4) 0.3695(3) 0.83363(19) 0.0219(9) Uani 1.000000 .
H37a H 0.9257(4) 0.4055(3) 0.83966(19) 0.0262(11) Uiso 1.000000 R
H37b H 0.9668(4) 0.3175(3) 0.85499(19) 0.0262(11) Uiso 1.000000 R
C23 C -0.0996(5) 0.0552(2) 0.1822(2) 0.0234(9) Uani 1.000000 .
H23a H -0.0120(5) 0.0297(2) 0.1691(2) 0.0281(11) Uiso 1.000000 R
H23b H -0.1799(5) 0.0183(2) 0.1885(2) 0.0281(11) Uiso 1.000000 R
C12 C 0.1684(5) 0.3925(2) 0.3447(2) 0.0239(9) Uani 1.000000 .
H12 H 0.1557(5) 0.3780(2) 0.3907(2) 0.0287(11) Uiso 1.000000 R
C21 C -0.1503(5) 0.1726(2) 0.0344(2) 0.0239(9) Uani 1.000000 .
H21 H -0.1468(5) 0.2219(2) 0.0437(2) 0.0287(11) Uiso 1.000000 R
C5 C 0.3863(5) 0.5596(2) 0.0387(2) 0.0225(9) Uani 1.000000 .
H5 H 0.3703(5) 0.5063(2) 0.0537(2) 0.0270(11) Uiso 1.000000 R
C44 C 0.7118(5) -0.2046(3) 1.0967(2) 0.0224(9) Uani 1.000000 .
H44a H 0.6906(5) -0.2600(3) 1.1037(2) 0.0268(11) Uiso 1.000000 R
H44b H 0.8128(5) -0.1978(3) 1.0994(2) 0.0268(11) Uiso 1.000000 R
C16 C -0.1982(5) 0.0840(3) -0.1024(2) 0.0216(9) Uani 1.000000 .
H16a H -0.1662(5) 0.0332(3) -0.1086(2) 0.0259(11) Uiso 1.000000 R
H16b H -0.3003(5) 0.0861(3) -0.1046(2) 0.0259(11) Uiso 1.000000 R
C4 C 0.3939(5) 0.5897(3) -0.0235(2) 0.0241(9) Uani 1.000000 .
H4 H 0.3812(5) 0.5572(3) -0.0508(2) 0.0289(11) Uiso 1.000000 R
C9 C 0.4109(5) 0.6127(2) 0.18392(19) 0.0212(9) Uani 1.000000 .
H9a H 0.5000(5) 0.6437(2) 0.17149(19) 0.0255(11) Uiso 1.000000 R
H9b H 0.3313(5) 0.6475(2) 0.18783(19) 0.0255(11) Uiso 1.000000 R
C51 C 0.5240(5) -0.0374(3) 0.8326(2) 0.0231(9) Uani 1.000000 .
H51a H 0.4381(5) -0.0711(3) 0.8444(2) 0.0277(11) Uiso 1.000000 R
H51b H 0.5092(5) 0.0062(3) 0.8535(2) 0.0277(11) Uiso 1.000000 R
C63 C 0.0894(5) 0.1007(3) 0.3855(2) 0.0289(11) Uani 1.000000 .
C19 C -0.1415(5) 0.0361(3) 0.0651(2) 0.0231(9) Uani 1.000000 .
H19 H -0.1313(5) -0.0085(3) 0.0953(2) 0.0278(11) Uiso 1.000000 R
C7 C 0.4243(5) 0.6845(2) 0.0575(2) 0.0224(9) Uani 1.000000 .
H7 H 0.4322(5) 0.7173(2) 0.0852(2) 0.0269(11) Uiso 1.000000 R
C52 C 0.5549(5) -0.0093(3) 0.7631(2) 0.0252(10) Uani 1.000000 .
H52 H 0.5695(5) -0.0536(3) 0.7424(2) 0.0303(12) Uiso 1.000000 R
C32 C 1.2130(5) 0.3997(3) 1.0071(2) 0.0266(10) Uani 1.000000 .
H32 H 1.2969(5) 0.4015(3) 1.0243(2) 0.0319(12) Uiso 1.000000 R
C47 C 0.5584(5) -0.0875(2) 0.9590(2) 0.0236(9) Uani 1.000000 .
H47 H 0.4822(5) -0.0549(2) 0.9515(2) 0.0284(11) Uiso 1.000000 R
C8 C 0.4349(4) 0.7136(3) -0.0054(2) 0.0221(9) Uani 1.000000 .
H8 H 0.4528(4) 0.7668(3) -0.0207(2) 0.0266(11) Uiso 1.000000 R
C46 C 0.5794(5) -0.1184(3) 1.0188(2) 0.0238(9) Uani 1.000000 .
H46 H 0.5172(5) -0.1054(3) 1.0522(2) 0.0286(11) Uiso 1.000000 R
C30 C 1.0731(5) 0.4056(2) 1.11120(19) 0.0230(9) Uani 1.000000 .
H30a H 1.0110(5) 0.4480(2) 1.11847(19) 0.0276(11) Uiso 1.000000 R
H30b H 1.1677(5) 0.4177(2) 1.11971(19) 0.0276(11) Uiso 1.000000 R
C53 C 0.6844(5) 0.0430(3) 0.7460(2) 0.0274(10) Uani 1.000000 .
H53a H 0.6652(5) 0.0892(3) 0.7632(2) 0.0329(12) Uiso 1.000000 R
H53b H 0.7632(5) 0.0167(3) 0.7643(2) 0.0329(12) Uiso 1.000000 R
C22 C -0.1687(5) 0.1648(3) -0.0236(2) 0.0257(10) Uani 1.000000 .
H22 H -0.1772(5) 0.2092(3) -0.0542(2) 0.0308(12) Uiso 1.000000 R
C18 C -0.1613(5) 0.0298(3) 0.0064(2) 0.0250(10) Uani 1.000000 .
H18 H -0.1654(5) -0.0193(3) -0.0030(2) 0.0300(12) Uiso 1.000000 R
C50 C 0.7781(5) -0.1845(3) 0.9820(2) 0.0264(10) Uani 1.000000 .
H50 H 0.8531(5) -0.2180(3) 0.9894(2) 0.0317(12) Uiso 1.000000 R
C57 C 0.5911(6) 0.4605(3) 0.3874(2) 0.0331(12) Uani 1.000000 .
C2 C 0.4277(5) 0.7030(2) -0.1144(2) 0.0225(9) Uani 1.000000 .
H2c H 0.3322(5) 0.7177(2) -0.1228(2) 0.0270(11) Uiso 1.000000 R
H2d H 0.4888(5) 0.7498(2) -0.1249(2) 0.0270(11) Uiso 1.000000 R
C35 C 0.9712(5) 0.3862(3) 0.9574(2) 0.0282(10) Uani 1.000000 .
H35 H 0.8876(5) 0.3795(3) 0.9412(2) 0.0339(12) Uiso 1.000000 R
C49 C 0.7610(5) -0.1537(3) 0.9221(2) 0.0267(10) Uani 1.000000 .
H49 H 0.8243(5) -0.1655(3) 0.8885(2) 0.0320(12) Uiso 1.000000 R
C67 C 0.3678(5) 0.0755(3) 0.5360(2) 0.0284(10) Uani 1.000000 .
H67a H 0.4470(5) 0.0826(3) 0.5012(2) 0.0341(12) Uiso 1.000000 R
H67b H 0.3171(5) 0.1239(3) 0.5329(2) 0.0341(12) Uiso 1.000000 R
C61 C 0.8722(5) 0.4058(3) 0.5360(2) 0.0314(11) Uani 1.000000 .
H61a H 0.8208(5) 0.3592(3) 0.5330(2) 0.0377(13) Uiso 1.000000 R
H61b H 0.9506(5) 0.4166(3) 0.5008(2) 0.0377(13) Uiso 1.000000 R
C27 C -0.2766(6) 0.2689(3) 0.3218(2) 0.0305(11) Uani 1.000000 .
H27a H -0.1839(17) 0.2731(6) 0.3342(14) 0.0457(16) Uiso 1.000000 GR
H27b H -0.267(4) 0.2813(8) 0.2767(3) 0.0457(16) Uiso 1.000000 GR
H27c H -0.3403(19) 0.3046(3) 0.3391(13) 0.0457(16) Uiso 1.000000 GR
C14 C 0.2328(6) 0.3264(3) 0.3202(2) 0.0315(11) Uani 1.000000 .
H14a H 0.240(4) 0.3373(9) 0.2752(3) 0.0473(16) Uiso 1.000000 GR
H14b H 0.3269(16) 0.3183(13) 0.3316(14) 0.0473(16) Uiso 1.000000 GR
H14c H 0.173(2) 0.2804(5) 0.3378(13) 0.0473(16) Uiso 1.000000 GR
C33 C 1.2230(5) 0.3980(3) 0.9445(2) 0.0305(11) Uani 1.000000 .
H33 H 1.3125(5) 0.4018(3) 0.9190(2) 0.0366(13) Uiso 1.000000 R
C66 C 0.2673(6) 0.0131(3) 0.5291(2) 0.0339(12) Uani 1.000000 .
H66a H 0.3110(6) -0.0370(3) 0.5397(2) 0.0406(14) Uiso 1.000000 R
H66b H 0.1793(6) 0.0125(3) 0.5588(2) 0.0406(14) Uiso 1.000000 R
C36 C 0.9645(5) 0.3917(3) 1.0186(2) 0.0325(11) Uani 1.000000 .
H36 H 0.8747(5) 0.3905(3) 1.0436(2) 0.0390(13) Uiso 1.000000 R
C64 C 0.1530(6) 0.0947(3) 0.4449(2) 0.0370(12) Uani 1.000000 .
H64a H 0.0759(6) 0.0985(3) 0.4789(2) 0.0444(15) Uiso 1.000000 R
H64b H 0.2187(6) 0.1390(3) 0.4395(2) 0.0444(15) Uiso 1.000000 R
C38 C 1.0474(5) 0.3721(3) 0.7654(2) 0.0336(12) Uani 1.000000 .
H38 H 1.0651(5) 0.4267(3) 0.7436(2) 0.0403(14) Uiso 1.000000 R
C40 C 1.3185(6) 0.2787(3) 0.6701(3) 0.0383(12) Uani 1.000000 .
H40 H 1.3833(6) 0.2691(3) 0.7014(3) 0.0460(15) Uiso 1.000000 R
C39 C 1.1758(6) 0.3298(3) 0.7516(2) 0.0327(11) Uani 1.000000 .
H39a H 1.1569(6) 0.2748(3) 0.7695(2) 0.0393(13) Uiso 1.000000 R
H39b H 1.2521(6) 0.3477(3) 0.7707(2) 0.0393(13) Uiso 1.000000 R
C28 C -0.4821(5) 0.1754(3) 0.3300(3) 0.0347(12) Uani 1.000000 .
H28a H -0.4803(11) 0.193(2) 0.2855(4) 0.0520(17) Uiso 1.000000 GR
H28b H -0.5082(18) 0.1208(4) 0.3419(16) 0.0520(17) Uiso 1.000000 GR
H28c H -0.5514(8) 0.2040(17) 0.3524(14) 0.0520(17) Uiso 1.000000 GR
C13 C 0.0250(5) 0.4116(3) 0.3270(3) 0.0380(13) Uani 1.000000 .
H13a H -0.0026(19) 0.4610(11) 0.3366(17) 0.0571(19) Uiso 1.000000 GR
H13b H 0.0290(12) 0.414(2) 0.2827(4) 0.0571(19) Uiso 1.000000 GR
H13c H -0.0445(10) 0.3720(12) 0.3502(14) 0.0571(19) Uiso 1.000000 GR
C58 C 0.6555(7) 0.4348(3) 0.4460(3) 0.0431(14) Uani 1.000000 .
H58a H 0.5792(7) 0.4131(3) 0.4802(3) 0.0517(17) Uiso 1.000000 R
H58b H 0.7215(7) 0.3936(3) 0.4399(3) 0.0517(17) Uiso 1.000000 R
C65 C 0.2302(6) 0.0236(3) 0.4637(2) 0.0356(12) Uani 1.000000 .
H65a H 0.3183(6) 0.0246(3) 0.4340(2) 0.0427(14) Uiso 1.000000 R
H65b H 0.1714(6) -0.0209(3) 0.4616(2) 0.0427(14) Uiso 1.000000 R
C60 C 0.7725(6) 0.4717(3) 0.5297(2) 0.0394(13) Uani 1.000000 .
H60a H 0.6854(6) 0.4571(3) 0.5600(2) 0.0472(16) Uiso 1.000000 R
H60b H 0.8173(6) 0.5161(3) 0.5400(2) 0.0472(16) Uiso 1.000000 R
C54 C 0.8256(6) 0.1350(3) 0.6616(3) 0.0426(14) Uani 1.000000 .
C59 C 0.7323(6) 0.4957(3) 0.4647(3) 0.0393(12) Uani 1.000000 .
H59a H 0.8193(6) 0.5108(3) 0.4344(3) 0.0472(15) Uiso 1.000000 R
H59b H 0.6727(6) 0.5409(3) 0.4635(3) 0.0472(15) Uiso 1.000000 R
C56 C 0.7462(7) 0.2069(3) 0.6646(3) 0.0480(15) Uani 1.000000 .
H56a H 0.8128(8) 0.2507(4) 0.654(2) 0.072(2) Uiso 1.000000 GR
H56b H 0.679(3) 0.2133(14) 0.6353(15) 0.072(2) Uiso 1.000000 GR
H56c H 0.695(4) 0.2034(11) 0.7065(6) 0.072(2) Uiso 1.000000 GR
C41 C 1.2391(8) 0.2048(4) 0.6718(3) 0.0569(18) Uani 1.000000 .
H41a H 1.191(4) 0.2106(10) 0.6356(12) 0.085(3) Uiso 1.000000 GR
H41b H 1.3056(11) 0.1633(7) 0.671(2) 0.085(3) Uiso 1.000000 GR
H41c H 1.169(4) 0.1927(15) 0.7094(12) 0.085(3) Uiso 1.000000 GR
C42 C 1.4054(8) 0.3054(5) 0.6065(3) 0.068(2) Uani 1.000000 .
H42a H 1.465(4) 0.2640(12) 0.5959(11) 0.102(3) Uiso 1.000000 GR
H42b H 1.3422(8) 0.320(3) 0.5760(5) 0.102(3) Uiso 1.000000 GR
H42c H 1.465(4) 0.350(2) 0.6065(8) 0.102(3) Uiso 1.000000 GR
O24 O -0.0767(4) 0.2552(2) 0.44758(17) 0.0339(8) Uani 1.000000 .
H24a H -0.054(6) 0.223(2) 0.424(2) 0.0508(12) Uiso 1.000000 G
H24b H -0.144(5) 0.232(3) 0.476(2) 0.0508(12) Uiso 1.000000 G
O22 O 1.1496(4) 0.2795(3) 0.5024(2) 0.0456(10) Uani 1.000000 .
O21 O 0.4224(4) 0.2731(2) 0.44817(16) 0.0323(8) Uani 1.000000 .
H21a H 0.447(6) 0.3197(10) 0.429(2) 0.0484(12) Uiso 1.000000 G
H21b H 0.352(4) 0.278(3) 0.477(2) 0.0484(12) Uiso 1.000000 G
O23 O -0.3515(3) 0.2179(2) 0.50201(17) 0.0364(9) Uani 1.000000 .
H23c H -0.425(3) 0.239(3) 0.488(2) 0.0545(13) Uiso 1.000000 G
H23d H -0.383(5) 0.196(3) 0.5401(10) 0.0545(13) Uiso 1.000000 G
H22a H 1.089(7) 0.264(4) 0.539(3) 0.046(17) Uiso 1.000000 .
H22b H 1.074(7) 0.273(4) 0.484(3) 0.052(18) Uiso 1.000000 .
C55 C 0.9105(8) 0.1407(5) 0.6019(3) 0.0626(19) Uani 1.000000 .
H55a H 0.970(4) 0.1873(16) 0.5919(11) 0.094(3) Uiso 1.000000 GR
H55b H 0.970(4) 0.0962(16) 0.6025(8) 0.094(3) Uiso 1.000000 GR
H55c H 0.8489(8) 0.142(3) 0.5707(5) 0.094(3) Uiso 1.000000 GR
H54 H 0.8905(6) 0.1288(3) 0.6930(3) 0.0512(17) Uiso 1.000000 R


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
O2 C6 1.373(5) . ?
O2 C9 1.426(5) . ?
O5 C20 1.372(5) . ?
O5 C23 1.418(5) . ?
O19 C68 1.263(5) . ?
O15 C62 1.258(5) . ?
O8 C34 1.385(5) . ?
O8 C37 1.412(5) . ?
O16 C62 1.246(5) . ?
O20 C68 1.253(5) . ?
O7 C29 1.231(5) . ?
O12 H12a 0.8400 . ?
O12 C52 1.423(5) . ?
O11 C48 1.377(5) . ?
O11 C51 1.412(5) . ?
O9 H9 0.8400 . ?
O9 C38 1.428(6) . ?
O1 C1 1.231(5) . ?
O10 C43 1.223(5) . ?
O17 C63 1.247(6) . ?
O4 C15 1.231(5) . ?
O14 C57 1.248(7) . ?
O3 H3 0.8400 . ?
O3 C10 1.413(5) . ?
O18 C63 1.255(6) . ?
O6 H6 0.8400 . ?
O6 C24 1.401(6) . ?
N2 H2a 0.9200 . ?
N2 H2b 0.9200 . ?
N2 C11 1.490(5) . ?
N2 C12 1.508(6) . ?
N4 H4a 0.9200 . ?
N4 H4b 0.9200 . ?
N4 C25 1.492(5) . ?
N4 C26 1.505(5) . ?
N8 H8a 0.9200 . ?
N8 H8b 0.9200 . ?
N8 C53 1.499(6) . ?
N8 C54 1.510(6) . ?
N7 H7a 0.8800 . ?
N7 H7b 0.8800 . ?
N7 C43 1.329(6) . ?
N3 H3a 0.8800 . ?
N3 H3b 0.8800 . ?
N3 C15 1.330(6) . ?
N1 H1a 0.8800 . ?
N1 H1b 0.8800 . ?
N1 C1 1.340(6) . ?
N6 H6a 0.9200 . ?
N6 H6b 0.9200 . ?
N6 C40 1.492(6) . ?
N6 C39 1.515(6) . ?
N5 H5a 0.8800 . ?
N5 H5b 0.8800 . ?
N5 C29 1.348(6) . ?
O13 C57 1.248(7) . ?
C20 C21 1.399(6) . ?
C20 C19 1.389(6) . ?
C6 C5 1.376(6) . ?
C6 C7 1.397(6) . ?
C34 C35 1.386(6) . ?
C34 C33 1.372(6) . ?
C62 C61 1.516(6) . ?
C45 C44 1.524(6) . ?
C45 C46 1.389(6) . ?
C45 C50 1.391(6) . ?
C29 C30 1.513(6) . ?
C3 C4 1.393(6) . ?
C3 C8 1.377(6) . ?
C3 C2 1.520(6) . ?
C1 C2 1.508(6) . ?
C43 C44 1.512(6) . ?
C25 H25a 0.9900 . ?
C25 H25b 0.9900 . ?
C25 C24 1.531(6) . ?
C31 C32 1.378(7) . ?
C31 C30 1.521(6) . ?
C31 C36 1.381(6) . ?
C68 C67 1.517(6) . ?
C15 C16 1.505(6) . ?
C11 H11a 0.9900 . ?
C11 H11b 0.9900 . ?
C11 C10 1.525(6) . ?
C17 C16 1.527(6) . ?
C17 C22 1.392(6) . ?
C17 C18 1.377(6) . ?
C24 H24 1.0000 . ?
C24 C23 1.516(6) . ?
C26 H26 1.0000 . ?
C26 C27 1.512(6) . ?
C26 C28 1.527(6) . ?
C48 C47 1.360(6) . ?
C48 C49 1.407(6) . ?
C10 H10 1.0000 . ?
C10 C9 1.517(6) . ?
C37 H37a 0.9900 . ?
C37 H37b 0.9900 . ?
C37 C38 1.516(6) . ?
C23 H23a 0.9900 . ?
C23 H23b 0.9900 . ?
C12 H12 1.0000 . ?
C12 C14 1.501(7) . ?
C12 C13 1.512(7) . ?
C21 H21 0.9500 . ?
C21 C22 1.376(7) . ?
C5 H5 0.9500 . ?
C5 C4 1.379(6) . ?
C44 H44a 0.9900 . ?
C44 H44b 0.9900 . ?
C16 H16a 0.9900 . ?
C16 H16b 0.9900 . ?
C4 H4 0.9500 . ?
C9 H9a 0.9900 . ?
C9 H9b 0.9900 . ?
C51 H51a 0.9900 . ?
C51 H51b 0.9900 . ?
C51 C52 1.519(6) . ?
C63 C64 1.535(6) . ?
C19 H19 0.9500 . ?
C19 C18 1.386(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.389(6) . ?
C52 H52 1.0000 . ?
C52 C53 1.508(6) . ?
C32 H32 0.9500 . ?
C32 C33 1.399(7) . ?
C47 H47 0.9500 . ?
C47 C46 1.389(6) . ?
C8 H8 0.9500 . ?
C46 H46 0.9500 . ?
C30 H30a 0.9900 . ?
C30 H30b 0.9900 . ?
C53 H53a 0.9900 . ?
C53 H53b 0.9900 . ?
C22 H22 0.9500 . ?
C18 H18 0.9500 . ?
C50 H50 0.9500 . ?
C50 C49 1.380(7) . ?
C57 C58 1.526(7) . ?
C2 H2c 0.9900 . ?
C2 H2d 0.9900 . ?
C35 H35 0.9500 . ?
C35 C36 1.389(7) . ?
C49 H49 0.9500 . ?
C67 H67a 0.9900 . ?
C67 H67b 0.9900 . ?
C67 C66 1.526(7) . ?
C61 H61a 0.9900 . ?
C61 H61b 0.9900 . ?
C61 C60 1.519(7) . ?
C27 H27a 0.9800 . ?
C27 H27b 0.9800 . ?
C27 H27c 0.9800 . ?
C14 H14a 0.9800 . ?
C14 H14b 0.9800 . ?
C14 H14c 0.9800 . ?
C33 H33 0.9500 . ?
C66 H66a 0.9900 . ?
C66 H66b 0.9900 . ?
C66 C65 1.539(7) . ?
C36 H36 0.9500 . ?
C64 H64a 0.9900 . ?
C64 H64b 0.9900 . ?
C64 C65 1.493(7) . ?
C38 H38 1.0000 . ?
C38 C39 1.473(7) . ?
C40 H40 1.0000 . ?
C40 C41 1.520(9) . ?
C40 C42 1.520(9) . ?
C39 H39a 0.9900 . ?
C39 H39b 0.9900 . ?
C28 H28a 0.9800 . ?
C28 H28b 0.9800 . ?
C28 H28c 0.9800 . ?
C13 H13a 0.9800 . ?
C13 H13b 0.9800 . ?
C13 H13c 0.9800 . ?
C58 H58a 0.9900 . ?
C58 H58b 0.9900 . ?
C58 C59 1.481(8) . ?
C65 H65a 0.9900 . ?
C65 H65b 0.9900 . ?
C60 H60a 0.9900 . ?
C60 H60b 0.9900 . ?
C60 C59 1.543(7) . ?
C54 C56 1.504(8) . ?
C54 C55 1.440(9) . ?
C54 H54 1.0000 . ?
C59 H59a 0.9900 . ?
C59 H59b 0.9900 . ?
C56 H56a 0.9800 . ?
C56 H56b 0.9800 . ?
C56 H56c 0.9800 . ?
C41 H41a 0.9800 . ?
C41 H41b 0.9800 . ?
C41 H41c 0.9800 . ?
C42 H42a 0.9800 . ?
C42 H42b 0.9800 . ?
C42 H42c 0.9800 . ?
O24 H24a 0.8700 . ?
O24 H24b 0.8700 . ?
O22 H22a 0.92(7) . ?
O22 H22b 0.91(7) . ?
O21 H21a 0.8701 . ?
O21 H21b 0.8700 . ?
O23 H23c 0.8701 . ?
O23 H23d 0.8699 . ?
C55 H55a 0.9800 . ?
C55 H55b 0.9800 . ?
C55 H55c 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
C9 O2 C6 117.5(3) . . ?
C23 O5 C20 117.4(3) . . ?
C37 O8 C34 118.1(3) . . ?
C52 O12 H12a 109.5 . . ?
C51 O11 C48 119.1(3) . . ?
C38 O9 H9 109.5 . . ?
C10 O3 H3 109.5 . . ?
C24 O6 H6 109.5 . . ?
H2b N2 H2a 107.3 . . ?
C11 N2 H2a 108.1(2) . . ?
C11 N2 H2b 108.1(2) . . ?
C12 N2 H2a 108.1(2) . . ?
C12 N2 H2b 108.1(2) . . ?
C12 N2 C11 117.0(3) . . ?
H4b N4 H4a 107.3 . . ?
C25 N4 H4a 108.1(2) . . ?
C25 N4 H4b 108.1(2) . . ?
C26 N4 H4a 108.1(2) . . ?
C26 N4 H4b 108.1(2) . . ?
C26 N4 C25 116.7(3) . . ?
H8b N8 H8a 108.2 . . ?
C53 N8 H8a 109.7(2) . . ?
C53 N8 H8b 109.7(2) . . ?
C54 N8 H8a 109.7(3) . . ?
C54 N8 H8b 109.7(3) . . ?
C54 N8 C53 109.8(4) . . ?
H7b N7 H7a 120.0 . . ?
C43 N7 H7a 120.0 . . ?
C43 N7 H7b 120.0 . . ?
H3b N3 H3a 120.0 . . ?
C15 N3 H3a 120.0 . . ?
C15 N3 H3b 120.0 . . ?
H1b N1 H1a 120.0 . . ?
C1 N1 H1a 120.0 . . ?
C1 N1 H1b 120.0 . . ?
H6b N6 H6a 108.3 . . ?
C40 N6 H6a 109.9(3) . . ?
C40 N6 H6b 109.9(3) . . ?
C39 N6 H6a 109.9(3) . . ?
C39 N6 H6b 109.9(2) . . ?
C39 N6 C40 108.8(4) . . ?
H5b N5 H5a 120.0 . . ?
C29 N5 H5a 120.0 . . ?
C29 N5 H5b 120.0 . . ?
C21 C20 O5 116.2(4) . . ?
C19 C20 O5 124.4(4) . . ?
C19 C20 C21 119.4(4) . . ?
C5 C6 O2 114.6(4) . . ?
C7 C6 O2 125.5(4) . . ?
C7 C6 C5 119.9(4) . . ?
C35 C34 O8 123.4(4) . . ?
C33 C34 O8 116.1(4) . . ?
C33 C34 C35 120.5(4) . . ?
O16 C62 O15 122.8(4) . . ?
C61 C62 O15 118.5(4) . . ?
C61 C62 O16 118.8(4) . . ?
C46 C45 C44 124.3(4) . . ?
C50 C45 C44 118.4(4) . . ?
C50 C45 C46 117.3(4) . . ?
N5 C29 O7 122.4(4) . . ?
C30 C29 O7 122.5(4) . . ?
C30 C29 N5 115.0(4) . . ?
C8 C3 C4 118.6(4) . . ?
C2 C3 C4 121.8(4) . . ?
C2 C3 C8 119.6(4) . . ?
N1 C1 O1 122.4(4) . . ?
C2 C1 O1 121.7(4) . . ?
C2 C1 N1 115.8(4) . . ?
N7 C43 O10 122.0(4) . . ?
C44 C43 O10 122.1(4) . . ?
C44 C43 N7 115.9(4) . . ?
H25a C25 N4 109.9(2) . . ?
H25b C25 N4 109.9(2) . . ?
H25b C25 H25a 108.3 . . ?
C24 C25 N4 109.1(3) . . ?
C24 C25 H25a 109.9(2) . . ?
C24 C25 H25b 109.9(2) . . ?
C30 C31 C32 121.5(4) . . ?
C36 C31 C32 117.8(4) . . ?
C36 C31 C30 120.7(4) . . ?
O20 C68 O19 122.6(4) . . ?
C67 C68 O19 117.5(4) . . ?
C67 C68 O20 119.9(4) . . ?
N3 C15 O4 121.7(4) . . ?
C16 C15 O4 121.4(4) . . ?
C16 C15 N3 116.9(4) . . ?
H11a C11 N2 109.8(2) . . ?
H11b C11 N2 109.8(2) . . ?
H11b C11 H11a 108.2 . . ?
C10 C11 N2 109.6(3) . . ?
C10 C11 H11a 109.8(2) . . ?
C10 C11 H11b 109.8(2) . . ?
C22 C17 C16 121.9(4) . . ?
C18 C17 C16 119.8(4) . . ?
C18 C17 C22 118.3(4) . . ?
C25 C24 O6 110.3(4) . . ?
H24 C24 O6 108.2(2) . . ?
H24 C24 C25 108.2(2) . . ?
C23 C24 O6 111.6(4) . . ?
C23 C24 C25 110.3(3) . . ?
C23 C24 H24 108.2(2) . . ?
H26 C26 N4 107.1(2) . . ?
C27 C26 N4 110.6(4) . . ?
C27 C26 H26 107.1(2) . . ?
C28 C26 N4 110.5(3) . . ?
C28 C26 H26 107.1(3) . . ?
C28 C26 C27 114.2(4) . . ?
C47 C48 O11 125.5(4) . . ?
C49 C48 O11 113.9(4) . . ?
C49 C48 C47 120.6(4) . . ?
C11 C10 O3 109.5(3) . . ?
H10 C10 O3 108.9(2) . . ?
H10 C10 C11 108.9(2) . . ?
C9 C10 O3 109.5(3) . . ?
C9 C10 C11 111.1(3) . . ?
C9 C10 H10 108.9(2) . . ?
H37a C37 O8 110.0(2) . . ?
H37b C37 O8 110.0(2) . . ?
H37b C37 H37a 108.4 . . ?
C38 C37 O8 108.6(4) . . ?
C38 C37 H37a 110.0(3) . . ?
C38 C37 H37b 110.0(3) . . ?
C24 C23 O5 108.9(3) . . ?
H23a C23 O5 109.9(2) . . ?
H23a C23 C24 109.9(2) . . ?
H23b C23 O5 109.9(2) . . ?
H23b C23 C24 109.9(2) . . ?
H23b C23 H23a 108.3 . . ?
H12 C12 N2 107.3(2) . . ?
C14 C12 N2 110.4(4) . . ?
C14 C12 H12 107.3(3) . . ?
C13 C12 N2 110.7(4) . . ?
C13 C12 H12 107.3(3) . . ?
C13 C12 C14 113.4(4) . . ?
H21 C21 C20 120.2(3) . . ?
C22 C21 C20 119.6(4) . . ?
C22 C21 H21 120.2(3) . . ?
H5 C5 C6 119.6(2) . . ?
C4 C5 C6 120.8(4) . . ?
C4 C5 H5 119.6(3) . . ?
C43 C44 C45 114.8(3) . . ?
H44a C44 C45 108.6(2) . . ?
H44a C44 C43 108.6(2) . . ?
H44b C44 C45 108.6(2) . . ?
H44b C44 C43 108.6(2) . . ?
H44b C44 H44a 107.6 . . ?
C17 C16 C15 112.3(3) . . ?
H16a C16 C15 109.1(2) . . ?
H16a C16 C17 109.1(2) . . ?
H16b C16 C15 109.1(2) . . ?
H16b C16 C17 109.1(2) . . ?
H16b C16 H16a 107.9 . . ?
C5 C4 C3 120.2(4) . . ?
H4 C4 C3 119.9(2) . . ?
H4 C4 C5 119.9(3) . . ?
C10 C9 O2 106.6(3) . . ?
H9a C9 O2 110.4(2) . . ?
H9a C9 C10 110.4(2) . . ?
H9b C9 O2 110.4(2) . . ?
H9b C9 C10 110.4(2) . . ?
H9b C9 H9a 108.6 . . ?
H51a C51 O11 110.4(2) . . ?
H51b C51 O11 110.4(2) . . ?
H51b C51 H51a 108.6 . . ?
C52 C51 O11 106.4(4) . . ?
C52 C51 H51a 110.4(2) . . ?
C52 C51 H51b 110.4(2) . . ?
O18 C63 O17 123.4(4) . . ?
C64 C63 O17 115.5(4) . . ?
C64 C63 O18 121.0(5) . . ?
H19 C19 C20 120.1(3) . . ?
C18 C19 C20 119.8(4) . . ?
C18 C19 H19 120.1(3) . . ?
H7 C7 C6 120.7(2) . . ?
C8 C7 C6 118.5(4) . . ?
C8 C7 H7 120.7(3) . . ?
C51 C52 O12 106.6(4) . . ?
H52 C52 O12 110.0(2) . . ?
H52 C52 C51 110.0(2) . . ?
C53 C52 O12 110.1(4) . . ?
C53 C52 C51 109.9(4) . . ?
C53 C52 H52 110.0(3) . . ?
H32 C32 C31 119.3(3) . . ?
C33 C32 C31 121.4(4) . . ?
C33 C32 H32 119.3(3) . . ?
H47 C47 C48 120.6(3) . . ?
C46 C47 C48 118.8(4) . . ?
C46 C47 H47 120.6(3) . . ?
C7 C8 C3 121.9(4) . . ?
H8 C8 C3 119.0(2) . . ?
H8 C8 C7 119.0(3) . . ?
C47 C46 C45 122.6(4) . . ?
H46 C46 C45 118.7(3) . . ?
H46 C46 C47 118.7(3) . . ?
C31 C30 C29 111.4(3) . . ?
H30a C30 C29 109.3(2) . . ?
H30a C30 C31 109.3(2) . . ?
H30b C30 C29 109.3(2) . . ?
H30b C30 C31 109.3(2) . . ?
H30b C30 H30a 108.0 . . ?
C52 C53 N8 111.6(4) . . ?
H53a C53 N8 109.3(2) . . ?
H53a C53 C52 109.3(3) . . ?
H53b C53 N8 109.3(2) . . ?
H53b C53 C52 109.3(3) . . ?
H53b C53 H53a 108.0 . . ?
C21 C22 C17 121.5(4) . . ?
H22 C22 C17 119.2(3) . . ?
H22 C22 C21 119.2(3) . . ?
C19 C18 C17 121.4(4) . . ?
H18 C18 C17 119.3(3) . . ?
H18 C18 C19 119.3(3) . . ?
H50 C50 C45 119.3(3) . . ?
C49 C50 C45 121.4(4) . . ?
C49 C50 H50 119.3(3) . . ?
O13 C57 O14 123.4(4) . . ?
C58 C57 O14 114.7(5) . . ?
C58 C57 O13 122.0(5) . . ?
C1 C2 C3 111.8(3) . . ?
H2c C2 C3 109.3(2) . . ?
H2c C2 C1 109.3(2) . . ?
H2d C2 C3 109.3(2) . . ?
H2d C2 C1 109.3(2) . . ?
H2d C2 H2c 107.9 . . ?
H35 C35 C34 120.6(3) . . ?
C36 C35 C34 118.8(4) . . ?
C36 C35 H35 120.6(3) . . ?
C50 C49 C48 119.3(4) . . ?
H49 C49 C48 120.4(3) . . ?
H49 C49 C50 120.4(3) . . ?
H67a C67 C68 108.5(3) . . ?
H67b C67 C68 108.5(2) . . ?
H67b C67 H67a 107.5 . . ?
C66 C67 C68 115.3(4) . . ?
C66 C67 H67a 108.5(3) . . ?
C66 C67 H67b 108.5(3) . . ?
H61a C61 C62 108.4(3) . . ?
H61b C61 C62 108.4(3) . . ?
H61b C61 H61a 107.5 . . ?
C60 C61 C62 115.4(4) . . ?
C60 C61 H61a 108.4(3) . . ?
C60 C61 H61b 108.4(3) . . ?
H27a C27 C26 109.5 . . ?
H27b C27 C26 109.5 . . ?
H27b C27 H27a 109.5 . . ?
H27c C27 C26 109.5 . . ?
H27c C27 H27a 109.5 . . ?
H27c C27 H27b 109.5 . . ?
H14a C14 C12 109.5 . . ?
H14b C14 C12 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 C12 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 109.5 . . ?
C32 C33 C34 119.3(4) . . ?
H33 C33 C34 120.4(3) . . ?
H33 C33 C32 120.4(3) . . ?
H66a C66 C67 108.9(3) . . ?
H66b C66 C67 108.9(3) . . ?
H66b C66 H66a 107.7 . . ?
C65 C66 C67 113.2(4) . . ?
C65 C66 H66a 108.9(3) . . ?
C65 C66 H66b 108.9(3) . . ?
C35 C36 C31 122.0(4) . . ?
H36 C36 C31 119.0(3) . . ?
H36 C36 C35 119.0(3) . . ?
H64a C64 C63 108.4(3) . . ?
H64b C64 C63 108.4(3) . . ?
H64b C64 H64a 107.5 . . ?
C65 C64 C63 115.5(4) . . ?
C65 C64 H64a 108.4(3) . . ?
C65 C64 H64b 108.4(3) . . ?
C37 C38 O9 105.6(4) . . ?
H38 C38 O9 108.6(3) . . ?
H38 C38 C37 108.6(3) . . ?
C39 C38 O9 111.8(4) . . ?
C39 C38 C37 113.6(4) . . ?
C39 C38 H38 108.6(3) . . ?
H40 C40 N6 109.0(2) . . ?
C41 C40 N6 112.7(5) . . ?
C41 C40 H40 109.0(3) . . ?
C42 C40 N6 107.9(5) . . ?
C42 C40 H40 109.0(3) . . ?
C42 C40 C41 109.1(6) . . ?
C38 C39 N6 110.7(4) . . ?
H39a C39 N6 109.5(3) . . ?
H39a C39 C38 109.5(3) . . ?
H39b C39 N6 109.5(2) . . ?
H39b C39 C38 109.5(3) . . ?
H39b C39 H39a 108.1 . . ?
H28a C28 C26 109.5 . . ?
H28b C28 C26 109.5 . . ?
H28b C28 H28a 109.5 . . ?
H28c C28 C26 109.5 . . ?
H28c C28 H28a 109.5 . . ?
H28c C28 H28b 109.5 . . ?
H13a C13 C12 109.5 . . ?
H13b C13 C12 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 C12 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?
H58a C58 C57 108.5(3) . . ?
H58b C58 C57 108.5(3) . . ?
H58b C58 H58a 107.5 . . ?
C59 C58 C57 115.0(5) . . ?
C59 C58 H58a 108.5(3) . . ?
C59 C58 H58b 108.5(3) . . ?
C64 C65 C66 113.4(4) . . ?
H65a C65 C66 108.9(3) . . ?
H65a C65 C64 108.9(3) . . ?
H65b C65 C66 108.9(3) . . ?
H65b C65 C64 108.9(3) . . ?
H65b C65 H65a 107.7 . . ?
H60a C60 C61 108.8(3) . . ?
H60b C60 C61 108.8(3) . . ?
H60b C60 H60a 107.7 . . ?
C59 C60 C61 113.7(4) . . ?
C59 C60 H60a 108.8(3) . . ?
C59 C60 H60b 108.8(3) . . ?
C56 C54 N8 111.2(4) . . ?
C55 C54 N8 111.1(5) . . ?
C55 C54 C56 110.8(6) . . ?
H54 C54 N8 107.9(3) . . ?
H54 C54 C56 107.9(3) . . ?
H54 C54 C55 107.9(4) . . ?
C60 C59 C58 113.5(5) . . ?
H59a C59 C58 108.9(4) . . ?
H59a C59 C60 108.9(3) . . ?
H59b C59 C58 108.9(3) . . ?
H59b C59 C60 108.9(3) . . ?
H59b C59 H59a 107.7 . . ?
H56a C56 C54 109.5 . . ?
H56b C56 C54 109.5 . . ?
H56b C56 H56a 109.5 . . ?
H56c C56 C54 109.5 . . ?
H56c C56 H56a 109.5 . . ?
H56c C56 H56b 109.5 . . ?
H41a C41 C40 109.5 . . ?
H41b C41 C40 109.5 . . ?
H41b C41 H41a 109.5 . . ?
H41c C41 C40 109.5 . . ?
H41c C41 H41a 109.5 . . ?
H41c C41 H41b 109.5 . . ?
H42a C42 C40 109.5 . . ?
H42b C42 C40 109.5 . . ?
H42b C42 H42a 109.5 . . ?
H42c C42 C40 109.5 . . ?
H42c C42 H42a 109.5 . . ?
H42c C42 H42b 109.5 . . ?
H24b O24 H24a 104.5 . . ?
H22b O22 H22a 86(5) . . ?
H21b O21 H21a 104.5 . . ?
H23d O23 H23c 104.5 . . ?
H55a C55 C54 109.5 . . ?
H55b C55 C54 109.5 . . ?
H55b C55 H55a 109.5 . . ?
H55c C55 C54 109.5 . . ?
H55c C55 H55a 109.5 . . ?
H55c C55 H55b 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
O2 C6 C5 C4 -178.7(4) . . . . ?
O2 C6 C7 C8 177.1(4) . . . . ?
O2 C9 C10 O3 72.2(4) . . . . ?
O2 C9 C10 C11 -48.8(4) . . . . ?
O5 C20 C21 C22 179.9(4) . . . . ?
O5 C20 C19 C18 179.6(4) . . . . ?
O5 C23 C24 O6 -72.9(4) . . . . ?
O5 C23 C24 C25 50.1(4) . . . . ?
O19 C68 C67 C66 166.2(4) . . . . ?
O15 C62 C61 C60 14.6(5) . . . . ?
O8 C34 C35 C36 -176.6(5) . . . . ?
O8 C34 C33 C32 179.7(4) . . . . ?
O8 C37 C38 O9 173.3(4) . . . . ?
O8 C37 C38 C39 50.4(4) . . . . ?
O16 C62 C61 C60 -166.3(5) . . . . ?
O20 C68 C67 C66 -15.3(5) . . . . ?
O7 C29 C30 C31 -79.8(4) . . . . ?
O12 C52 C51 O11 179.6(3) . . . . ?
O12 C52 C53 N8 -68.3(4) . . . . ?
O11 C48 C47 C46 -179.3(4) . . . . ?
O11 C48 C49 C50 -179.8(4) . . . . ?
O11 C51 C52 C53 -61.1(4) . . . . ?
O9 C38 C39 N6 66.1(4) . . . . ?
O1 C1 C2 C3 -76.2(5) . . . . ?
O10 C43 C44 C45 66.4(5) . . . . ?
O17 C63 C64 C65 162.5(5) . . . . ?
O4 C15 C16 C17 71.6(5) . . . . ?
O14 C57 C58 C59 -160.4(5) . . . . ?
O3 C10 C11 N2 77.1(3) . . . . ?
O18 C63 C64 C65 -17.9(6) . . . . ?
O6 C24 C25 N4 -77.4(4) . . . . ?
N2 C11 C10 C9 -161.8(3) . . . . ?
N4 C25 C24 C23 158.8(3) . . . . ?
N8 C53 C52 C51 174.5(4) . . . . ?
N7 C43 C44 C45 -111.5(4) . . . . ?
N3 C15 C16 C17 -106.5(4) . . . . ?
N1 C1 C2 C3 100.2(4) . . . . ?
N6 C39 C38 C37 -174.5(4) . . . . ?
N5 C29 C30 C31 96.6(4) . . . . ?
O13 C57 C58 C59 19.2(6) . . . . ?
C20 C21 C22 C17 0.5(5) . . . . ?
C20 C19 C18 C17 0.6(5) . . . . ?
C6 C5 C4 C3 1.3(5) . . . . ?
C6 C7 C8 C3 1.7(5) . . . . ?
C34 C35 C36 C31 -2.3(6) . . . . ?
C34 C33 C32 C31 -3.9(6) . . . . ?
C62 C61 C60 C59 169.7(5) . . . . ?
C45 C46 C47 C48 -1.2(5) . . . . ?
C45 C50 C49 C48 -0.8(5) . . . . ?
C29 C30 C31 C32 -112.9(4) . . . . ?
C29 C30 C31 C36 67.2(5) . . . . ?
C68 C67 C66 C65 -169.5(4) . . . . ?
C15 C16 C17 C22 38.7(4) . . . . ?
C15 C16 C17 C18 -141.7(4) . . . . ?
C63 C64 C65 C66 -169.1(5) . . . . ?
C57 C58 C59 C60 169.5(5) . . . . ?
C67 C66 C65 C64 -63.2(5) . . . . ?
C61 C60 C59 C58 62.3(6) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_systematic        'Atenolol adipate hydrate'
_chemical_name_common            'Atenolol adipate hydrate'
_exptl_crystal_colour            Colorless
_chemical_melting_point          436-438
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
_chemical_properties_physical    Heat-sensitive
