#------------------------------------------------------------------------------
#$Date: 2020-04-08 02:28:59 +0300 (Wed, 08 Apr 2020) $
#$Revision: 250460 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/82/4038219.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4038219
loop_
_publ_author_name
'Helberg, Julian'
'Ampßler, Torsten'
'Zipse, Hendrik'
_publ_section_title
;
 Pyridinyl Amide Ion Pairs as Lewis Base Organocatalysts.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00114
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C12 H17 N O2'
_chemical_formula_sum            'C12 H17 N O2'
_chemical_formula_weight         207.26
_chemical_name_common            ta02
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_block_code                C12H17NO2_uv331_zipse
_audit_creation_method           'APEX3 v2015.9-RC7'
_audit_update_record             20-Jun-16
_cell_angle_alpha                90
_cell_angle_beta                 102.0210(10)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   18.1807(6)
_cell_length_b                   27.4981(7)
_cell_length_c                   9.6395(2)
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    153.(2)
_cell_measurement_theta_max      30.4788
_cell_measurement_theta_min      3.1447
_cell_volume                     4713.4(2)
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 740)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XT, VERSION 2014/4'
_diffrn_ambient_temperature      153.(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture TXS'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0728
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            29658
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_min         3.145
_diffrn_source                   'rotating anode (TXS)'
_diffrn_source_current           50
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9604
_exptl_absorpt_correction_T_min  0.8905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;

Flack x determined using 3934 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     565
_refine_ls_number_reflns         14193
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0572
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0640P)²+0.7848P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1410
_reflns_Friedel_coverage         0.998
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                10647
_reflns_number_total             14193
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00114_si_002.cif
_cod_data_source_block           uv331
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4038219
_shelx_estimated_absorpt_t_min   0.992
_shelx_estimated_absorpt_t_max   0.998
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.23895(13) 0.44910(7) 0.4731(2) 0.0319(5) Uani 1 1 d . . . . .
O2 O 0.19825(13) 0.47693(8) 0.6640(2) 0.0354(5) Uani 1 1 d . . . . .
O3 O 0.38161(13) 0.54763(8) 0.5351(2) 0.0339(5) Uani 1 1 d . . . . .
O4 O 0.42291(13) 0.52012(8) 0.3440(2) 0.0354(5) Uani 1 1 d . . . . .
O5 O 0.76935(12) 0.42237(7) 0.52406(19) 0.0284(4) Uani 1 1 d . . . . .
O6 O 0.79237(13) 0.38717(7) 0.32553(18) 0.0324(5) Uani 1 1 d . . . . .
O7 O 0.83344(12) 0.59246(7) 0.4905(2) 0.0314(5) Uani 1 1 d . . . . .
O8 O 0.79722(13) 0.64945(8) 0.32103(19) 0.0356(5) Uani 1 1 d . . . . .
N1 N 0.17359(15) 0.51718(9) 0.4509(3) 0.0310(6) Uani 1 1 d . . . . .
H1 H 0.183(2) 0.5135(14) 0.362(5) 0.055(12) Uiso 1 1 d . . . . .
N2 N 0.44523(15) 0.47934(9) 0.5562(2) 0.0287(5) Uani 1 1 d . . . . .
H2 H 0.437(2) 0.4812(12) 0.644(4) 0.036(9) Uiso 1 1 d . . . . .
N3 N 0.83691(14) 0.35553(8) 0.5479(2) 0.0258(5) Uani 1 1 d . . . . .
H3 H 0.8320(19) 0.3592(11) 0.632(3) 0.031(9) Uiso 1 1 d . . . . .
N4 N 0.76965(14) 0.65583(9) 0.5407(2) 0.0288(5) Uani 1 1 d . . . . .
H4 H 0.7774(16) 0.6419(10) 0.623(3) 0.017(7) Uiso 1 1 d . . . . .
C1 C 0.20275(17) 0.48127(10) 0.5409(3) 0.0265(6) Uani 1 1 d . . . . .
C2 C 0.12999(17) 0.55672(11) 0.4790(3) 0.0274(6) Uani 1 1 d . . . . .
C3 C 0.1239(2) 0.57103(12) 0.6145(3) 0.0382(8) Uani 1 1 d . . . . .
H3A H 0.1496 0.5534 0.6949 0.046 Uiso 1 1 calc R U . . .
C4 C 0.0804(2) 0.61100(12) 0.6320(3) 0.0428(8) Uani 1 1 d . . . . .
H4A H 0.0767 0.6202 0.7253 0.051 Uiso 1 1 calc R U . . .
C5 C 0.04222(19) 0.63799(12) 0.5188(3) 0.0352(7) Uani 1 1 d . . . . .
C6 C 0.0495(2) 0.62330(13) 0.3838(3) 0.0390(7) Uani 1 1 d . . . . .
H6 H 0.0244 0.6412 0.3034 0.047 Uiso 1 1 calc R U . . .
C7 C 0.09232(18) 0.58346(12) 0.3642(3) 0.0342(7) Uani 1 1 d . . . . .
H7 H 0.0960 0.5743 0.2709 0.041 Uiso 1 1 calc R U . . .
C8 C -0.0040(2) 0.68157(14) 0.5403(4) 0.0510(9) Uani 1 1 d . . . . .
H8A H -0.0092 0.7031 0.4579 0.076 Uiso 1 1 calc R U . . .
H8B H 0.0210 0.6991 0.6257 0.076 Uiso 1 1 calc R U . . .
H8C H -0.0539 0.6709 0.5514 0.076 Uiso 1 1 calc R U . . .
C9 C 0.27850(18) 0.41032(11) 0.5608(3) 0.0301(6) Uani 1 1 d . . . . .
H9A H 0.2440 0.3937 0.6125 0.036 Uiso 1 1 calc R U . . .
H9B H 0.3210 0.4239 0.6313 0.036 Uiso 1 1 calc R U . . .
C10 C 0.30701(17) 0.37498(11) 0.4667(3) 0.0310(6) Uani 1 1 d . . . . .
H10A H 0.3410 0.3919 0.4146 0.037 Uiso 1 1 calc R U . . .
H10B H 0.2642 0.3617 0.3963 0.037 Uiso 1 1 calc R U . . .
C11 C 0.3493(2) 0.33345(12) 0.5529(3) 0.0382(7) Uani 1 1 d . . . . .
H11A H 0.3893 0.3472 0.6282 0.046 Uiso 1 1 calc R U . . .
H11B H 0.3140 0.3154 0.5997 0.046 Uiso 1 1 calc R U . . .
C12 C 0.3842(2) 0.29839(14) 0.4649(4) 0.0492(9) Uani 1 1 d . . . . .
H12A H 0.4095 0.2722 0.5256 0.074 Uiso 1 1 calc R U . . .
H12B H 0.4210 0.3157 0.4218 0.074 Uiso 1 1 calc R U . . .
H12C H 0.3449 0.2846 0.3901 0.074 Uiso 1 1 calc R U . . .
C13 C 0.41727(17) 0.51562(10) 0.4667(3) 0.0270(6) Uani 1 1 d . . . . .
C14 C 0.48921(17) 0.43986(10) 0.5294(3) 0.0266(6) Uani 1 1 d . . . . .
C15 C 0.49707(19) 0.42520(11) 0.3946(3) 0.0342(7) Uani 1 1 d . . . . .
H15 H 0.4719 0.4423 0.3129 0.041 Uiso 1 1 calc R U . . .
C16 C 0.5419(2) 0.38546(12) 0.3808(3) 0.0394(8) Uani 1 1 d . . . . .
H16 H 0.5473 0.3761 0.2886 0.047 Uiso 1 1 calc R U . . .
C17 C 0.57924(19) 0.35886(12) 0.4969(4) 0.0366(7) Uani 1 1 d . . . . .
C18 C 0.57053(18) 0.37350(12) 0.6302(3) 0.0368(7) Uani 1 1 d . . . . .
H18 H 0.5953 0.3560 0.7115 0.044 Uiso 1 1 calc R U . . .
C19 C 0.52605(18) 0.41343(11) 0.6470(3) 0.0316(6) Uani 1 1 d . . . . .
H19 H 0.5208 0.4227 0.7393 0.038 Uiso 1 1 calc R U . . .
C20 C 0.6270(2) 0.31524(14) 0.4809(4) 0.0525(10) Uani 1 1 d . . . . .
H20A H 0.6775 0.3196 0.5397 0.079 Uiso 1 1 calc R U . . .
H20B H 0.6306 0.3118 0.3813 0.079 Uiso 1 1 calc R U . . .
H20C H 0.6041 0.2859 0.5113 0.079 Uiso 1 1 calc R U . . .
C21 C 0.34348(18) 0.58702(11) 0.4495(3) 0.0311(6) Uani 1 1 d . . . . .
H21A H 0.3008 0.5742 0.3779 0.037 Uiso 1 1 calc R U . . .
H21B H 0.3786 0.6037 0.3994 0.037 Uiso 1 1 calc R U . . .
C22 C 0.31528(18) 0.62218(11) 0.5465(3) 0.0320(6) Uani 1 1 d . . . . .
H22A H 0.3585 0.6356 0.6156 0.038 Uiso 1 1 calc R U . . .
H22B H 0.2826 0.6047 0.6001 0.038 Uiso 1 1 calc R U . . .
C23 C 0.2715(2) 0.66344(12) 0.4636(4) 0.0383(7) Uani 1 1 d . . . . .
H23A H 0.2305 0.6497 0.3901 0.046 Uiso 1 1 calc R U . . .
H23B H 0.3053 0.6819 0.4148 0.046 Uiso 1 1 calc R U . . .
C24 C 0.2378(2) 0.69794(14) 0.5562(4) 0.0475(9) Uani 1 1 d . . . . .
H24A H 0.2126 0.7248 0.4982 0.071 Uiso 1 1 calc R U . . .
H24B H 0.2778 0.7110 0.6312 0.071 Uiso 1 1 calc R U . . .
H24C H 0.2013 0.6804 0.5992 0.071 Uiso 1 1 calc R U . . .
C25 C 0.79929(15) 0.38784(9) 0.4537(3) 0.0233(5) Uani 1 1 d . . . . .
C26 C 0.87753(15) 0.31420(9) 0.5203(3) 0.0231(5) Uani 1 1 d . . . . .
C27 C 0.90383(18) 0.28334(11) 0.6345(3) 0.0302(6) Uani 1 1 d . . . . .
H27 H 0.8936 0.2905 0.7249 0.036 Uiso 1 1 calc R U . . .
C28 C 0.94490(19) 0.24217(11) 0.6168(3) 0.0334(7) Uani 1 1 d . . . . .
H28 H 0.9631 0.2218 0.6961 0.040 Uiso 1 1 calc R U . . .
C29 C 0.96010(16) 0.23008(11) 0.4857(3) 0.0290(6) Uani 1 1 d . . . . .
C30 C 0.93393(18) 0.26120(11) 0.3740(3) 0.0327(6) Uani 1 1 d . . . . .
H30 H 0.9438 0.2537 0.2834 0.039 Uiso 1 1 calc R U . . .
C31 C 0.89369(16) 0.30312(11) 0.3892(3) 0.0290(6) Uani 1 1 d . . . . .
H31 H 0.8773 0.3241 0.3105 0.035 Uiso 1 1 calc R U . . .
C32 C 1.00439(19) 0.18483(11) 0.4681(4) 0.0381(7) Uani 1 1 d . . . . .
H32A H 0.9965 0.1765 0.3672 0.057 Uiso 1 1 calc R U . . .
H32B H 0.9874 0.1579 0.5201 0.057 Uiso 1 1 calc R U . . .
H32C H 1.0580 0.1908 0.5055 0.057 Uiso 1 1 calc R U . . .
C33 C 0.72218(17) 0.45776(10) 0.4370(3) 0.0287(6) Uani 1 1 d . . . . .
H33A H 0.6786 0.4415 0.3758 0.034 Uiso 1 1 calc R U . . .
H33B H 0.7510 0.4750 0.3756 0.034 Uiso 1 1 calc R U . . .
C34 C 0.69562(17) 0.49320(11) 0.5358(3) 0.0281(6) Uani 1 1 d . . . . .
H34A H 0.7396 0.5096 0.5951 0.034 Uiso 1 1 calc R U . . .
H34B H 0.6690 0.4753 0.5997 0.034 Uiso 1 1 calc R U . . .
C35 C 0.64308(19) 0.53119(11) 0.4531(3) 0.0356(7) Uani 1 1 d . . . . .
H35A H 0.6707 0.5502 0.3932 0.043 Uiso 1 1 calc R U . . .
H35B H 0.6008 0.5145 0.3896 0.043 Uiso 1 1 calc R U . . .
C36 C 0.6118(2) 0.56585(13) 0.5498(4) 0.0433(8) Uani 1 1 d . . . . .
H36A H 0.5790 0.5898 0.4921 0.065 Uiso 1 1 calc R U . . .
H36B H 0.6534 0.5827 0.6124 0.065 Uiso 1 1 calc R U . . .
H36C H 0.5829 0.5474 0.6071 0.065 Uiso 1 1 calc R U . . .
C37 C 0.79931(16) 0.63395(10) 0.4400(3) 0.0266(6) Uani 1 1 d . . . . .
C38 C 0.72826(15) 0.69980(10) 0.5300(3) 0.0254(5) Uani 1 1 d . . . . .
C39 C 0.71083(18) 0.71761(12) 0.6544(3) 0.0322(6) Uani 1 1 d . . . . .
H39 H 0.7272 0.7006 0.7411 0.039 Uiso 1 1 calc R U . . .
C40 C 0.66947(18) 0.76024(11) 0.6520(3) 0.0331(6) Uani 1 1 d . . . . .
H40 H 0.6573 0.7717 0.7375 0.040 Uiso 1 1 calc R U . . .
C41 C 0.64557(16) 0.78643(11) 0.5283(3) 0.0303(6) Uani 1 1 d . . . . .
C42 C 0.66414(18) 0.76820(12) 0.4057(3) 0.0342(7) Uani 1 1 d . . . . .
H42 H 0.6486 0.7856 0.3195 0.041 Uiso 1 1 calc R U . . .
C43 C 0.70478(18) 0.72525(11) 0.4047(3) 0.0306(6) Uani 1 1 d . . . . .
H43 H 0.7162 0.7136 0.3189 0.037 Uiso 1 1 calc R U . . .
C44 C 0.6012(2) 0.83252(12) 0.5282(4) 0.0421(8) Uani 1 1 d . . . . .
H44A H 0.6194 0.8570 0.4694 0.063 Uiso 1 1 calc R U . . .
H44B H 0.6073 0.8447 0.6255 0.063 Uiso 1 1 calc R U . . .
H44C H 0.5478 0.8259 0.4895 0.063 Uiso 1 1 calc R U . . .
C45 C 0.86465(17) 0.56358(11) 0.3899(3) 0.0310(6) Uani 1 1 d . . . . .
H45A H 0.8981 0.5838 0.3447 0.037 Uiso 1 1 calc R U . . .
H45B H 0.8238 0.5506 0.3148 0.037 Uiso 1 1 calc R U . . .
C46 C 0.90848(17) 0.52249(11) 0.4719(3) 0.0313(6) Uani 1 1 d . . . . .
H46A H 0.8758 0.5048 0.5252 0.038 Uiso 1 1 calc R U . . .
H46B H 0.9516 0.5360 0.5412 0.038 Uiso 1 1 calc R U . . .
C47 C 0.9374(2) 0.48718(11) 0.3744(3) 0.0382(7) Uani 1 1 d . . . . .
H47A H 0.9669 0.5053 0.3160 0.046 Uiso 1 1 calc R U . . .
H47B H 0.8941 0.4720 0.3095 0.046 Uiso 1 1 calc R U . . .
C48 C 0.9863(2) 0.44751(14) 0.4562(4) 0.0533(10) Uani 1 1 d . . . . .
H48A H 1.0035 0.4255 0.3894 0.080 Uiso 1 1 calc R U . . .
H48B H 0.9571 0.4291 0.5131 0.080 Uiso 1 1 calc R U . . .
H48C H 1.0300 0.4623 0.5189 0.080 Uiso 1 1 calc R U . . .
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'
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 O1 C9 115.5(2) . . ?
C13 O3 C21 115.7(2) . . ?
C25 O5 C33 115.9(2) . . ?
C37 O7 C45 116.0(2) . . ?
C1 N1 C2 127.2(2) . . ?
C1 N1 H1 114(3) . . ?
C2 N1 H1 119(3) . . ?
C13 N2 C14 127.4(2) . . ?
C13 N2 H2 117(2) . . ?
C14 N2 H2 116(2) . . ?
C25 N3 C26 128.0(2) . . ?
C25 N3 H3 115(2) . . ?
C26 N3 H3 116(2) . . ?
C37 N4 C38 128.0(2) . . ?
C37 N4 H4 116.6(19) . . ?
C38 N4 H4 115.4(19) . . ?
O2 C1 N1 127.2(3) . . ?
O2 C1 O1 123.3(3) . . ?
N1 C1 O1 109.6(2) . . ?
C7 C2 C3 118.5(3) . . ?
C7 C2 N1 117.5(2) . . ?
C3 C2 N1 123.9(3) . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C5 C4 C3 122.4(3) . . ?
C5 C4 H4A 118.8 . . ?
C3 C4 H4A 118.8 . . ?
C4 C5 C6 116.9(3) . . ?
C4 C5 C8 121.5(3) . . ?
C6 C5 C8 121.6(3) . . ?
C7 C6 C5 121.6(3) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C2 120.8(3) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 C10 108.4(2) . . ?
O1 C9 H9A 110.0 . . ?
C10 C9 H9A 110.0 . . ?
O1 C9 H9B 110.0 . . ?
C10 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
C9 C10 C11 110.8(2) . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C12 C11 C10 113.3(3) . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O4 C13 O3 123.9(3) . . ?
O4 C13 N2 127.0(3) . . ?
O3 C13 N2 109.1(2) . . ?
C15 C14 C19 118.8(3) . . ?
C15 C14 N2 124.6(3) . . ?
C19 C14 N2 116.6(2) . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 122.4(3) . . ?
C15 C16 H16 118.8 . . ?
C17 C16 H16 118.8 . . ?
C18 C17 C16 117.5(3) . . ?
C18 C17 C20 120.4(3) . . ?
C16 C17 C20 122.1(3) . . ?
C17 C18 C19 121.2(3) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C18 C19 C14 120.5(3) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21 C22 108.1(2) . . ?
O3 C21 H21A 110.1 . . ?
C22 C21 H21A 110.1 . . ?
O3 C21 H21B 110.1 . . ?
C22 C21 H21B 110.1 . . ?
H21A C21 H21B 108.4 . . ?
C21 C22 C23 111.3(2) . . ?
C21 C22 H22A 109.4 . . ?
C23 C22 H22A 109.4 . . ?
C21 C22 H22B 109.4 . . ?
C23 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
C22 C23 C24 113.0(3) . . ?
C22 C23 H23A 109.0 . . ?
C24 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
C24 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O6 C25 O5 123.7(2) . . ?
O6 C25 N3 127.2(2) . . ?
O5 C25 N3 109.1(2) . . ?
C31 C26 C27 118.8(2) . . ?
C31 C26 N3 124.5(2) . . ?
C27 C26 N3 116.7(2) . . ?
C28 C27 C26 120.4(3) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C29 121.4(3) . . ?
C27 C28 H28 119.3 . . ?
C29 C28 H28 119.3 . . ?
C30 C29 C28 117.4(3) . . ?
C30 C29 C32 121.9(3) . . ?
C28 C29 C32 120.7(3) . . ?
C29 C30 C31 122.4(3) . . ?
C29 C30 H30 118.8 . . ?
C31 C30 H30 118.8 . . ?
C30 C31 C26 119.6(3) . . ?
C30 C31 H31 120.2 . . ?
C26 C31 H31 120.2 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O5 C33 C34 107.3(2) . . ?
O5 C33 H33A 110.3 . . ?
C34 C33 H33A 110.3 . . ?
O5 C33 H33B 110.3 . . ?
C34 C33 H33B 110.3 . . ?
H33A C33 H33B 108.5 . . ?
C33 C34 C35 111.1(2) . . ?
C33 C34 H34A 109.4 . . ?
C35 C34 H34A 109.4 . . ?
C33 C34 H34B 109.4 . . ?
C35 C34 H34B 109.4 . . ?
H34A C34 H34B 108.0 . . ?
C36 C35 C34 112.5(3) . . ?
C36 C35 H35A 109.1 . . ?
C34 C35 H35A 109.1 . . ?
C36 C35 H35B 109.1 . . ?
C34 C35 H35B 109.1 . . ?
H35A C35 H35B 107.8 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O8 C37 O7 124.1(3) . . ?
O8 C37 N4 125.8(3) . . ?
O7 C37 N4 110.1(2) . . ?
C43 C38 C39 119.3(3) . . ?
C43 C38 N4 123.9(3) . . ?
C39 C38 N4 116.8(2) . . ?
C40 C39 C38 120.2(3) . . ?
C40 C39 H39 119.9 . . ?
C38 C39 H39 119.9 . . ?
C41 C40 C39 121.7(3) . . ?
C41 C40 H40 119.2 . . ?
C39 C40 H40 119.2 . . ?
C40 C41 C42 117.2(3) . . ?
C40 C41 C44 120.8(3) . . ?
C42 C41 C44 122.0(3) . . ?
C41 C42 C43 122.3(3) . . ?
C41 C42 H42 118.8 . . ?
C43 C42 H42 118.8 . . ?
C38 C43 C42 119.3(3) . . ?
C38 C43 H43 120.4 . . ?
C42 C43 H43 120.4 . . ?
C41 C44 H44A 109.5 . . ?
C41 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C41 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
O7 C45 C46 107.3(2) . . ?
O7 C45 H45A 110.3 . . ?
C46 C45 H45A 110.3 . . ?
O7 C45 H45B 110.3 . . ?
C46 C45 H45B 110.3 . . ?
H45A C45 H45B 108.5 . . ?
C45 C46 C47 111.6(2) . . ?
C45 C46 H46A 109.3 . . ?
C47 C46 H46A 109.3 . . ?
C45 C46 H46B 109.3 . . ?
C47 C46 H46B 109.3 . . ?
H46A C46 H46B 108.0 . . ?
C46 C47 C48 112.2(3) . . ?
C46 C47 H47A 109.2 . . ?
C48 C47 H47A 109.2 . . ?
C46 C47 H47B 109.2 . . ?
C48 C47 H47B 109.2 . . ?
H47A C47 H47B 107.9 . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.350(3) . ?
O1 C9 1.455(4) . ?
O2 C1 1.213(3) . ?
O3 C13 1.345(3) . ?
O3 C21 1.448(4) . ?
O4 C13 1.214(3) . ?
O5 C25 1.346(3) . ?
O5 C33 1.445(3) . ?
O6 C25 1.216(3) . ?
O7 C37 1.341(3) . ?
O7 C45 1.456(3) . ?
O8 C37 1.217(3) . ?
N1 C1 1.348(4) . ?
N1 C2 1.405(4) . ?
N1 H1 0.91(4) . ?
N2 C13 1.347(4) . ?
N2 C14 1.404(4) . ?
N2 H2 0.90(4) . ?
N3 C25 1.350(3) . ?
N3 C26 1.411(3) . ?
N3 H3 0.84(3) . ?
N4 C37 1.346(3) . ?
N4 C38 1.416(4) . ?
N4 H4 0.86(3) . ?
C2 C7 1.385(4) . ?
C2 C3 1.390(4) . ?
C3 C4 1.385(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.382(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.395(4) . ?
C5 C8 1.502(5) . ?
C6 C7 1.380(5) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.494(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.523(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.510(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 C15 1.395(4) . ?
C14 C19 1.395(4) . ?
C15 C16 1.386(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(4) . ?
C17 C20 1.508(5) . ?
C18 C19 1.393(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.507(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.515(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.517(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C26 C31 1.390(4) . ?
C26 C27 1.393(4) . ?
C27 C28 1.386(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.390(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.380(4) . ?
C29 C32 1.511(4) . ?
C30 C31 1.389(4) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C34 1.510(4) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.524(4) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.524(4) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C38 C43 1.385(4) . ?
C38 C39 1.391(4) . ?
C39 C40 1.390(4) . ?
C39 H39 0.9500 . ?
C40 C41 1.383(4) . ?
C40 H40 0.9500 . ?
C41 C42 1.389(4) . ?
C41 C44 1.503(4) . ?
C42 C43 1.394(4) . ?
C42 H42 0.9500 . ?
C43 H43 0.9500 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 C46 1.508(4) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 C47 1.519(4) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 C48 1.521(5) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.91(4) 2.01(4) 2.897(3) 166(4) 2_564
N2 H2 O4 0.90(4) 1.99(4) 2.887(3) 175(3) 2_565
N3 H3 O8 0.84(3) 2.06(3) 2.874(3) 162(3) 2_565
N4 H4 O6 0.86(3) 2.08(3) 2.938(3) 176(3) 2_565
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
C2 N1 C1 O2 -1.8(5) . . . . ?
C2 N1 C1 O1 177.9(3) . . . . ?
C9 O1 C1 O2 -5.1(4) . . . . ?
C9 O1 C1 N1 175.3(2) . . . . ?
C1 N1 C2 C7 -166.4(3) . . . . ?
C1 N1 C2 C3 15.1(5) . . . . ?
C7 C2 C3 C4 0.5(5) . . . . ?
N1 C2 C3 C4 179.0(3) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C3 C4 C5 C8 -179.3(4) . . . . ?
C4 C5 C6 C7 0.5(5) . . . . ?
C8 C5 C6 C7 179.6(3) . . . . ?
C5 C6 C7 C2 -0.3(5) . . . . ?
C3 C2 C7 C6 -0.2(5) . . . . ?
N1 C2 C7 C6 -178.8(3) . . . . ?
C1 O1 C9 C10 173.1(2) . . . . ?
O1 C9 C10 C11 179.9(3) . . . . ?
C9 C10 C11 C12 -175.9(3) . . . . ?
C21 O3 C13 O4 5.1(4) . . . . ?
C21 O3 C13 N2 -175.5(2) . . . . ?
C14 N2 C13 O4 2.6(5) . . . . ?
C14 N2 C13 O3 -176.8(3) . . . . ?
C13 N2 C14 C15 -15.8(5) . . . . ?
C13 N2 C14 C19 165.4(3) . . . . ?
C19 C14 C15 C16 -1.0(4) . . . . ?
N2 C14 C15 C16 -179.8(3) . . . . ?
C14 C15 C16 C17 0.7(5) . . . . ?
C15 C16 C17 C18 -0.2(5) . . . . ?
C15 C16 C17 C20 179.1(3) . . . . ?
C16 C17 C18 C19 -0.1(5) . . . . ?
C20 C17 C18 C19 -179.4(3) . . . . ?
C17 C18 C19 C14 -0.2(5) . . . . ?
C15 C14 C19 C18 0.7(4) . . . . ?
N2 C14 C19 C18 179.6(3) . . . . ?
C13 O3 C21 C22 -173.1(2) . . . . ?
O3 C21 C22 C23 -177.4(3) . . . . ?
C21 C22 C23 C24 176.3(3) . . . . ?
C33 O5 C25 O6 4.8(4) . . . . ?
C33 O5 C25 N3 -175.4(2) . . . . ?
C26 N3 C25 O6 1.0(5) . . . . ?
C26 N3 C25 O5 -178.9(2) . . . . ?
C25 N3 C26 C31 8.7(5) . . . . ?
C25 N3 C26 C27 -172.5(3) . . . . ?
C31 C26 C27 C28 -0.5(4) . . . . ?
N3 C26 C27 C28 -179.3(3) . . . . ?
C26 C27 C28 C29 -0.9(5) . . . . ?
C27 C28 C29 C30 1.2(5) . . . . ?
C27 C28 C29 C32 -179.5(3) . . . . ?
C28 C29 C30 C31 -0.2(5) . . . . ?
C32 C29 C30 C31 -179.5(3) . . . . ?
C29 C30 C31 C26 -1.2(5) . . . . ?
C27 C26 C31 C30 1.5(4) . . . . ?
N3 C26 C31 C30 -179.7(3) . . . . ?
C25 O5 C33 C34 -179.2(2) . . . . ?
O5 C33 C34 C35 -178.1(2) . . . . ?
C33 C34 C35 C36 176.8(3) . . . . ?
C45 O7 C37 O8 -4.4(4) . . . . ?
C45 O7 C37 N4 176.8(2) . . . . ?
C38 N4 C37 O8 2.2(5) . . . . ?
C38 N4 C37 O7 -179.0(3) . . . . ?
C37 N4 C38 C43 7.1(4) . . . . ?
C37 N4 C38 C39 -173.0(3) . . . . ?
C43 C38 C39 C40 0.8(4) . . . . ?
N4 C38 C39 C40 -179.1(3) . . . . ?
C38 C39 C40 C41 -1.0(5) . . . . ?
C39 C40 C41 C42 0.4(5) . . . . ?
C39 C40 C41 C44 -179.8(3) . . . . ?
C40 C41 C42 C43 0.3(5) . . . . ?
C44 C41 C42 C43 -179.4(3) . . . . ?
C39 C38 C43 C42 0.0(4) . . . . ?
N4 C38 C43 C42 179.9(3) . . . . ?
C41 C42 C43 C38 -0.6(5) . . . . ?
C37 O7 C45 C46 172.9(2) . . . . ?
O7 C45 C46 C47 174.5(2) . . . . ?
C45 C46 C47 C48 175.9(3) . . . . ?
