#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:17:34 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179622 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/86/4508605.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_4508605
loop_
_publ_author_name
'Goubert, Guillaume'
'Demers-Carpentier, Vincent'
'Loach, Richard P.'
'Lafleur-Lambert, Raphaél'
'Lemay, Jean-Christian'
'Boukouvalas, John'
'McBreen, Peter H.'
_publ_section_title
;
 Aminolactone Chiral Modifiers for Heterogeneous Asymmetric Hydrogenation:
 Corrected Structure of Pantoyl-Naphthylethylamine, In-Situ
 Hydrogenolysis, and Scanning Tunneling Microscopy Observation of
 Supramolecular Aminolactone/Substrate Assemblies on Pt(111)
;
_journal_issue                   12
_journal_name_full               'ACS Catalysis'
_journal_page_first              2677
_journal_paper_doi               10.1021/cs4007588
_journal_volume                  3
_journal_year                    2013
_chemical_absolute_configuration rmad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C18 H21 N O2'
_chemical_formula_sum            'C18 H21 N O2'
_chemical_formula_weight         283.36
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 107.3713(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.65410(16)
_cell_length_b                   8.25169(6)
_cell_length_c                   17.39574(12)
_cell_measurement_reflns_used    14357
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.65
_cell_measurement_theta_min      2.66
_cell_volume                     3103.55(4)
_computing_cell_refinement       'SAINT V7.68A(Bruker AXS, 2009)'
_computing_data_collection       'APEX2  (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A(Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Quazar MX'
_diffrn_radiation_source         'Incoatec I\muS Microsource '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20187
_diffrn_reflns_theta_full        70.95
_diffrn_reflns_theta_max         70.95
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_T_max  0.9634
_exptl_absorpt_correction_T_min  0.8735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), 2119 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.03(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         5337
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0301
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0672P)²+0.3734P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0852
_reflns_number_gt                5298
_reflns_number_total             5337
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cs4007588_si_002.cif
_cod_data_source_block           breen2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        3103.55(5)
_cod_original_sg_symbol_H-M      C2
_cod_database_code               4508605
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.16637(15) 0.4248(3) 0.98047(15) 0.0399(5) Uani 0.593(2) 1 d PDU A 1
C2 C 0.1627(9) 0.5654(10) 0.9920(5) 0.0258(17) Uani 0.593(2) 1 d PDU A 1
O3 O 0.18721(9) 0.6236(2) 1.07079(9) 0.0342(5) Uani 0.593(2) 1 d PD A 1
C4 C 0.18468(11) 0.7998(3) 1.07020(12) 0.0328(5) Uani 0.593(2) 1 d PD A 1
H4A H 0.2256 0.8463 1.0734 0.039 Uiso 0.593(2) 1 calc PR A 1
H4B H 0.1717 0.8404 1.1163 0.039 Uiso 0.593(2) 1 calc PR A 1
C5 C 0.1366(4) 0.8456(8) 0.9897(4) 0.0288(9) Uani 0.593(2) 1 d PDU A 1
C20 C 0.07175(11) 0.8374(3) 0.99859(15) 0.0361(6) Uani 0.593(2) 1 d PD A 1
H20A H 0.0413 0.8652 0.9471 0.054 Uiso 0.593(2) 1 calc PR A 1
H20B H 0.0685 0.9143 1.0400 0.054 Uiso 0.593(2) 1 calc PR A 1
H20C H 0.0638 0.7274 1.0143 0.054 Uiso 0.593(2) 1 calc PR A 1
C21 C 0.14976(11) 1.0155(3) 0.96281(14) 0.0326(5) Uani 0.593(2) 1 d PD A 1
H21A H 0.1192 1.0419 0.9113 0.049 Uiso 0.593(2) 1 calc PR A 1
H21B H 0.1913 1.0180 0.9565 0.049 Uiso 0.593(2) 1 calc PR A 1
H21C H 0.1472 1.0951 1.0035 0.049 Uiso 0.593(2) 1 calc PR A 1
O21 O 0.19427(15) 0.4602(5) 0.9992(2) 0.0372(8) Uani 0.407(2) 1 d PDU A 2
C22 C 0.1689(14) 0.5835(17) 0.9993(8) 0.0258(17) Uani 0.407(2) 1 d PDU A 2
O23 O 0.14114(13) 0.6235(4) 1.05726(14) 0.0410(7) Uani 0.407(2) 1 d PD A 2
C24 C 0.10737(16) 0.7743(5) 1.03677(19) 0.0341(8) Uani 0.407(2) 1 d PD A 2
H24A H 0.1131 0.8416 1.0856 0.041 Uiso 0.407(2) 1 calc PR A 2
H24B H 0.0627 0.7525 1.0128 0.041 Uiso 0.407(2) 1 calc PR A 2
C25 C 0.1328(6) 0.8612(12) 0.9767(7) 0.0288(9) Uani 0.407(2) 1 d PDU A 2
C30 C 0.08360(18) 0.9703(5) 0.9215(2) 0.0389(8) Uani 0.407(2) 1 d PD A 2
H30A H 0.1010 1.0254 0.8833 0.058 Uiso 0.407(2) 1 calc PR A 2
H30B H 0.0701 1.0511 0.9540 0.058 Uiso 0.407(2) 1 calc PR A 2
H30C H 0.0481 0.9043 0.8919 0.058 Uiso 0.407(2) 1 calc PR A 2
C31 C 0.19092(19) 0.9540(6) 1.0166(3) 0.0503(12) Uani 0.407(2) 1 d PD A 2
H31A H 0.2056 1.0073 0.9754 0.075 Uiso 0.407(2) 1 calc PR A 2
H31B H 0.2227 0.8792 1.0477 0.075 Uiso 0.407(2) 1 calc PR A 2
H31C H 0.1824 1.0359 1.0526 0.075 Uiso 0.407(2) 1 calc PR A 2
C6 C 0.14523(5) 0.70836(16) 0.93332(7) 0.0236(2) Uani 1 1 d D . .
H6A H 0.1037 0.6844 0.8946 0.028 Uiso 0.593(2) 1 calc PR A 1
H6B H 0.1050 0.6692 0.8962 0.028 Uiso 0.407(2) 1 calc PR A 2
N7 N 0.18755(4) 0.73852(13) 0.88619(6) 0.0233(2) Uani 1 1 d . A .
H7 H 0.2278(8) 0.749(2) 0.9170(10) 0.035(4) Uiso 1 1 d . . .
C8 C 0.18304(5) 0.61881(15) 0.82229(6) 0.0219(2) Uani 1 1 d . . .
H8 H 0.1860 0.5074 0.8457 0.026 Uiso 1 1 calc R A .
C9 C 0.12099(5) 0.63694(14) 0.75695(6) 0.0199(2) Uani 1 1 d . A .
C10 C 0.09195(6) 0.78496(16) 0.74320(7) 0.0254(2) Uani 1 1 d . . .
H10 H 0.1110 0.8756 0.7746 0.031 Uiso 1 1 calc R A .
C11 C 0.03458(6) 0.80559(16) 0.68360(7) 0.0275(3) Uani 1 1 d . A .
H11 H 0.0154 0.9092 0.6757 0.033 Uiso 1 1 calc R . .
C12 C 0.00638(5) 0.67828(16) 0.63720(7) 0.0262(3) Uani 1 1 d . . .
H12 H -0.0321 0.6936 0.5968 0.031 Uiso 1 1 calc R A .
C13 C 0.03436(5) 0.52269(15) 0.64905(7) 0.0223(2) Uani 1 1 d . A .
C14 C 0.00476(5) 0.38819(16) 0.60254(7) 0.0277(3) Uani 1 1 d . . .
H14 H -0.0341 0.4027 0.5628 0.033 Uiso 1 1 calc R A .
C15 C 0.03136(6) 0.23803(17) 0.61414(7) 0.0304(3) Uani 1 1 d . A .
H15 H 0.0110 0.1489 0.5826 0.036 Uiso 1 1 calc R . .
C16 C 0.08901(6) 0.21537(16) 0.67298(7) 0.0271(2) Uani 1 1 d . . .
H16 H 0.1075 0.1109 0.6806 0.033 Uiso 1 1 calc R A .
C17 C 0.11865(5) 0.34267(15) 0.71919(6) 0.0221(2) Uani 1 1 d . A .
H17 H 0.1575 0.3250 0.7585 0.026 Uiso 1 1 calc R . .
C18 C 0.09242(5) 0.50074(14) 0.70948(6) 0.0194(2) Uani 1 1 d . . .
C19 C 0.23660(5) 0.6451(2) 0.78691(7) 0.0317(3) Uani 1 1 d . A .
H19A H 0.2350 0.7560 0.7663 0.048 Uiso 1 1 calc R . .
H19B H 0.2331 0.5681 0.7429 0.048 Uiso 1 1 calc R . .
H19C H 0.2760 0.6280 0.8289 0.048 Uiso 1 1 calc R . .
O31 O 0.94527(6) 0.72881(14) 0.82534(7) 0.0475(3) Uani 1 1 d . . .
C32 C 0.95600(6) 0.58747(19) 0.82060(8) 0.0349(3) Uani 1 1 d . . .
O33 O 1.01203(5) 0.52283(16) 0.85921(6) 0.0467(3) Uani 1 1 d . . .
C34 C 1.01064(6) 0.3504(2) 0.84432(8) 0.0389(3) Uani 1 1 d . . .
H34A H 1.0355 0.2918 0.8929 0.047 Uiso 1 1 calc R . .
H34B H 1.0274 0.3257 0.7992 0.047 Uiso 1 1 calc R . .
C35 C 0.94242(5) 0.30093(17) 0.82302(7) 0.0269(3) Uani 1 1 d . . .
C36 C 0.91332(5) 0.45273(16) 0.77568(7) 0.0245(2) Uani 1 1 d . . .
H36 H 0.9191 0.4442 0.7210 0.029 Uiso 1 1 calc R . .
N37 N 0.84776(5) 0.47263(13) 0.76406(6) 0.0243(2) Uani 1 1 d . . .
H37 H 0.8417(7) 0.499(2) 0.8144(10) 0.033(4) Uiso 1 1 d . . .
C38 C 0.81830(6) 0.60403(16) 0.70813(7) 0.0287(3) Uani 1 1 d . . .
H38 H 0.8400 0.7085 0.7275 0.034 Uiso 1 1 calc R . .
C39 C 0.82184(5) 0.56785(15) 0.62369(7) 0.0227(2) Uani 1 1 d . . .
C40 C 0.80666(5) 0.41607(16) 0.59191(7) 0.0266(2) Uani 1 1 d . . .
H40 H 0.7944 0.3357 0.6232 0.032 Uiso 1 1 calc R . .
C41 C 0.80872(5) 0.37609(17) 0.51360(7) 0.0287(3) Uani 1 1 d . . .
H41 H 0.7977 0.2703 0.4927 0.034 Uiso 1 1 calc R . .
C42 C 0.82663(5) 0.49042(17) 0.46808(7) 0.0288(3) Uani 1 1 d . . .
H42 H 0.8287 0.4627 0.4160 0.035 Uiso 1 1 calc R . .
C43 C 0.84204(5) 0.64940(17) 0.49775(6) 0.0248(2) Uani 1 1 d . . .
C44 C 0.86110(6) 0.76813(19) 0.45125(7) 0.0322(3) Uani 1 1 d . . .
H44 H 0.8635 0.7406 0.3992 0.039 Uiso 1 1 calc R . .
C45 C 0.87609(6) 0.92142(19) 0.48000(8) 0.0357(3) Uani 1 1 d . . .
H45 H 0.8886 0.9997 0.4480 0.043 Uiso 1 1 calc R . .
C46 C 0.87297(6) 0.96342(17) 0.55725(8) 0.0311(3) Uani 1 1 d . . .
H46 H 0.8833 1.0703 0.5770 0.037 Uiso 1 1 calc R . .
C47 C 0.85517(5) 0.85153(16) 0.60401(7) 0.0253(2) Uani 1 1 d . . .
H47 H 0.8533 0.8821 0.6559 0.030 Uiso 1 1 calc R . .
C48 C 0.83937(5) 0.69065(15) 0.57651(6) 0.0211(2) Uani 1 1 d . . .
C49 C 0.75093(7) 0.6172(2) 0.70752(9) 0.0451(4) Uani 1 1 d . . .
H49A H 0.7295 0.5151 0.6882 0.068 Uiso 1 1 calc R . .
H49B H 0.7307 0.7057 0.6717 0.068 Uiso 1 1 calc R . .
H49C H 0.7493 0.6392 0.7622 0.068 Uiso 1 1 calc R . .
C50 C 0.92388(6) 0.2836(2) 0.90049(7) 0.0355(3) Uani 1 1 d . . .
H50A H 0.9338 0.3839 0.9319 0.053 Uiso 1 1 calc R . .
H50B H 0.9466 0.1931 0.9324 0.053 Uiso 1 1 calc R . .
H50C H 0.8794 0.2626 0.8867 0.053 Uiso 1 1 calc R . .
C51 C 0.92793(6) 0.14817(19) 0.77277(8) 0.0376(3) Uani 1 1 d . . .
H51A H 0.9475 0.0552 0.8056 0.056 Uiso 1 1 calc R . .
H51B H 0.9439 0.1584 0.7265 0.056 Uiso 1 1 calc R . .
H51C H 0.8830 0.1320 0.7537 0.056 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_publ_flag
O1 C2 O3 118.3(6) y
O1 C2 C6 131.2(7) y
O3 C2 C6 109.6(6) y
C2 O3 C4 109.4(3) y
O3 C4 C5 105.5(3) y
O3 C4 H4A 110.6 ?
C5 C4 H4A 110.6 ?
O3 C4 H4B 110.6 ?
C5 C4 H4B 110.6 ?
H4A C4 H4B 108.8 ?
C20 C5 C21 110.6(4) y
C20 C5 C4 109.7(5) y
C21 C5 C4 110.6(5) y
C20 C5 C6 109.8(5) y
C21 C5 C6 113.7(5) y
C4 C5 C6 102.0(4) y
C5 C20 H20A 109.5 ?
C5 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
C5 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
C5 C21 H21A 109.5 ?
C5 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
C5 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
O21 C22 O23 122.8(10) y
O21 C22 C6 130.8(9) y
O23 C22 C6 104.8(9) y
C22 O23 C24 110.4(4) y
O23 C24 C25 107.1(5) y
O23 C24 H24A 110.3 ?
C25 C24 H24A 110.3 ?
O23 C24 H24B 110.3 ?
C25 C24 H24B 110.3 ?
H24A C24 H24B 108.5 ?
C31 C25 C24 112.6(8) y
C31 C25 C30 111.4(7) y
C24 C25 C30 110.8(8) y
C31 C25 C6 112.4(8) y
C24 C25 C6 96.5(6) y
C30 C25 C6 112.4(7) y
C25 C30 H30A 109.5 ?
C25 C30 H30B 109.5 ?
H30A C30 H30B 109.5 ?
C25 C30 H30C 109.5 ?
H30A C30 H30C 109.5 ?
H30B C30 H30C 109.5 ?
C25 C31 H31A 109.5 ?
C25 C31 H31B 109.5 ?
H31A C31 H31B 109.5 ?
C25 C31 H31C 109.5 ?
H31A C31 H31C 109.5 ?
H31B C31 H31C 109.5 ?
N7 C6 C22 113.5(10) y
N7 C6 C2 115.1(6) y
N7 C6 C25 112.5(5) y
C22 C6 C25 105.1(6) y
C2 C6 C25 110.7(5) y
N7 C6 C5 117.4(3) y
C22 C6 C5 95.8(5) y
C2 C6 C5 101.4(4) y
N7 C6 H6A 107.5 ?
C22 C6 H6A 115.1 ?
C2 C6 H6A 107.5 ?
C25 C6 H6A 102.7 ?
C5 C6 H6A 107.5 ?
N7 C6 H6B 108.5 ?
C22 C6 H6B 108.5 ?
C2 C6 H6B 100.7 ?
C25 C6 H6B 108.5 ?
C5 C6 H6B 112.5 ?
C6 N7 C8 113.73(9) y
C6 N7 H7 113.3(10) ?
C8 N7 H7 109.7(11) ?
N7 C8 C9 109.75(9) y
N7 C8 C19 108.94(10) y
C9 C8 C19 110.51(9) y
N7 C8 H8 109.2 ?
C9 C8 H8 109.2 ?
C19 C8 H8 109.2 ?
C10 C9 C18 119.18(10) y
C10 C9 C8 120.18(10) y
C18 C9 C8 120.64(10) y
C9 C10 C11 121.57(11) y
C9 C10 H10 119.2 ?
C11 C10 H10 119.2 ?
C12 C11 C10 120.59(11) y
C12 C11 H11 119.7 ?
C10 C11 H11 119.7 ?
C11 C12 C13 120.10(10) y
C11 C12 H12 120.0 ?
C13 C12 H12 120.0 ?
C14 C13 C12 120.68(10) y
C14 C13 C18 119.67(11) y
C12 C13 C18 119.64(11) y
C15 C14 C13 120.85(11) y
C15 C14 H14 119.6 ?
C13 C14 H14 119.6 ?
C14 C15 C16 119.96(12) y
C14 C15 H15 120.0 ?
C16 C15 H15 120.0 ?
C17 C16 C15 120.62(12) y
C17 C16 H16 119.7 ?
C15 C16 H16 119.7 ?
C16 C17 C18 121.27(10) y
C16 C17 H17 119.4 ?
C18 C17 H17 119.4 ?
C17 C18 C13 117.62(10) y
C17 C18 C9 123.45(10) y
C13 C18 C9 118.92(10) y
C8 C19 H19A 109.5 ?
C8 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C8 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
O31 C32 O33 121.85(13) y
O31 C32 C36 129.28(14) y
O33 C32 C36 108.86(13) y
C32 O33 C34 109.36(11) y
O33 C34 C35 105.78(12) y
O33 C34 H34A 110.6 ?
C35 C34 H34A 110.6 ?
O33 C34 H34B 110.6 ?
C35 C34 H34B 110.6 ?
H34A C34 H34B 108.7 ?
C51 C35 C34 112.99(12) y
C51 C35 C50 111.15(12) y
C34 C35 C50 109.47(10) y
C51 C35 C36 112.67(10) y
C34 C35 C36 98.78(10) y
C50 C35 C36 111.18(11) y
N37 C36 C32 117.10(11) y
N37 C36 C35 115.20(9) y
C32 C36 C35 102.40(10) y
N37 C36 H36 107.2 ?
C32 C36 H36 107.2 ?
C35 C36 H36 107.2 ?
C36 N37 C38 114.74(9) y
C36 N37 H37 108.8(10) ?
C38 N37 H37 106.0(10) ?
N37 C38 C39 110.35(10) y
N37 C38 C49 108.12(10) y
C39 C38 C49 110.32(11) y
N37 C38 H38 109.3 ?
C39 C38 H38 109.3 ?
C49 C38 H38 109.3 ?
C40 C39 C48 119.62(10) y
C40 C39 C38 119.24(11) y
C48 C39 C38 121.12(11) y
C39 C40 C41 121.63(12) y
C39 C40 H40 119.2 ?
C41 C40 H40 119.2 ?
C42 C41 C40 119.78(12) y
C42 C41 H41 120.1 ?
C40 C41 H41 120.1 ?
C41 C42 C43 120.76(11) y
C41 C42 H42 119.6 ?
C43 C42 H42 119.6 ?
C42 C43 C44 121.11(11) y
C42 C43 C48 119.58(11) y
C44 C43 C48 119.30(12) y
C45 C44 C43 121.07(11) y
C45 C44 H44 119.5 ?
C43 C44 H44 119.5 ?
C44 C45 C46 119.95(12) y
C44 C45 H45 120.0 ?
C46 C45 H45 120.0 ?
C47 C46 C45 120.55(13) y
C47 C46 H46 119.7 ?
C45 C46 H46 119.7 ?
C46 C47 C48 121.31(11) y
C46 C47 H47 119.3 ?
C48 C47 H47 119.3 ?
C47 C48 C43 117.82(10) y
C47 C48 C39 123.58(10) y
C43 C48 C39 118.60(11) y
C38 C49 H49A 109.5 ?
C38 C49 H49B 109.5 ?
H49A C49 H49B 109.5 ?
C38 C49 H49C 109.5 ?
H49A C49 H49C 109.5 ?
H49B C49 H49C 109.5 ?
C35 C50 H50A 109.5 ?
C35 C50 H50B 109.5 ?
H50A C50 H50B 109.5 ?
C35 C50 H50C 109.5 ?
H50A C50 H50C 109.5 ?
H50B C50 H50C 109.5 ?
C35 C51 H51A 109.5 ?
C35 C51 H51B 109.5 ?
H51A C51 H51B 109.5 ?
C35 C51 H51C 109.5 ?
H51A C51 H51C 109.5 ?
H51B C51 H51C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 1.185(8) y
C2 O3 1.401(11) y
C2 C6 1.532(7) y
O3 C4 1.455(3) y
C4 C5 1.542(7) y
C4 H4a 0.9900 ?
C4 H4b 0.9900 ?
C5 C20 1.524(9) y
C5 C21 1.535(7) y
C5 C6 1.548(7) y
C20 H20a 0.9800 ?
C20 H20b 0.9800 ?
C20 H20c 0.9800 ?
C21 H21a 0.9800 ?
C21 H21b 0.9800 ?
C21 H21c 0.9800 ?
O21 C22 1.169(10) y
C22 O23 1.378(15) y
C22 C6 1.516(10) y
O23 C24 1.448(4) y
C24 C25 1.516(12) y
C24 H24a 0.9900 ?
C24 H24b 0.9900 ?
C25 C31 1.501(12) y
C25 C30 1.528(11) y
C25 C6 1.539(10) y
C30 H30a 0.9800 ?
C30 H30b 0.9800 ?
C30 H30c 0.9800 ?
C31 H31a 0.9800 ?
C31 H31b 0.9800 ?
C31 H31c 0.9800 ?
C6 N7 1.4570(14) y
C6 H6a 1.0000 ?
C6 H6b 1.0000 ?
N7 C8 1.4677(14) y
N7 H7 0.913(18) ?
C8 C9 1.5285(14) y
C8 C19 1.5310(14) y
C8 H8 1.0000 ?
C9 C10 1.3739(17) y
C9 C18 1.4300(15) y
C10 C11 1.4103(17) y
C10 H10 0.9500 ?
C11 C12 1.3621(19) y
C11 H11 0.9500 ?
C12 C13 1.4194(17) y
C12 H12 0.9500 ?
C13 C14 1.4185(17) y
C13 C18 1.4291(15) y
C14 C15 1.366(2) y
C14 H14 0.9500 ?
C15 C16 1.4107(18) y
C15 H15 0.9500 ?
C16 C17 1.3704(17) y
C16 H16 0.9500 ?
C17 C18 1.4223(16) y
C17 H17 0.9500 ?
C19 H19a 0.9800 ?
C19 H19b 0.9800 ?
C19 H19c 0.9800 ?
O31 C32 1.199(2) y
C32 O33 1.356(2) y
C32 C36 1.5266(17) y
O33 C34 1.445(2) y
C34 C35 1.5332(16) y
C34 H34a 0.9900 ?
C34 H34b 0.9900 ?
C35 C51 1.513(2) y
C35 C50 1.5333(15) y
C35 C36 1.5355(17) y
C36 N37 1.4471(15) y
C36 H36 1.0000 ?
N37 C38 1.4766(15) y
N37 H37 0.953(17) ?
C38 C39 1.5242(15) y
C38 C49 1.5269(19) y
C38 H38 1.0000 ?
C39 C40 1.3708(18) y
C39 C48 1.4328(16) y
C40 C41 1.4159(17) y
C40 H40 0.9500 ?
C41 C42 1.3688(19) y
C41 H41 0.9500 ?
C42 C43 1.4148(18) y
C42 H42 0.9500 ?
C43 C44 1.4174(18) y
C43 C48 1.4304(15) y
C44 C45 1.365(2) y
C44 H44 0.9500 ?
C45 C46 1.410(2) y
C45 H45 0.9500 ?
C46 C47 1.3684(18) y
C46 H46 0.9500 ?
C47 C48 1.4202(17) y
C47 H47 0.9500 ?
C49 H49a 0.9800 ?
C49 H49b 0.9800 ?
C49 H49c 0.9800 ?
C50 H50a 0.9800 ?
C50 H50b 0.9800 ?
C50 H50c 0.9800 ?
C51 H51a 0.9800 ?
C51 H51b 0.9800 ?
C51 H51c 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
_geom_hbond_publ_flag
N7 H7 O21 0.913(18) 2.599(18) 3.361(3) 141.5(15) 4_557 y
N7 H7 O1 0.913(18) 2.914(18) 3.756(3) 154.1(15) 4_557 y
N37 H37 O23 0.953(17) 2.380(17) 3.288(2) 159(14) 2_657 y
N37 H37 O3 0.953(17) 2.500(17) 3.4341(18) 166.8(14) 2_657 y
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_publ_flag
O1 C2 O3 C4 173.2(12) y
C6 C2 O3 C4 2.9(13) y
C2 O3 C4 C5 19.1(9) y
O3 C4 C5 C20 83.8(4) y
O3 C4 C5 C21 -153.9(4) y
O3 C4 C5 C6 -32.6(5) y
O21 C22 O23 C24 -173(2) y
C6 C22 O23 C24 -6(2) y
C22 O23 C24 C25 -19.6(15) y
O23 C24 C25 C31 -82.5(7) y
O23 C24 C25 C30 152.0(5) y
O23 C24 C25 C6 35.0(7) y
O21 C22 C6 N7 -41(4) y
O23 C22 C6 N7 152.9(13) y
O21 C22 C6 C2 61(7) y
O23 C22 C6 C2 -104(11) y
O21 C22 C6 C25 -165(3) y
O23 C22 C6 C25 29(2) y
O21 C22 C6 C5 -165(3) y
O23 C22 C6 C5 29.6(18) y
O1 C2 C6 N7 -64(2) y
O3 C2 C6 N7 104.5(9) y
O1 C2 C6 C22 -145(11) y
O3 C2 C6 C22 24(8) y
O1 C2 C6 C25 167.0(17) y
O3 C2 C6 C25 -24.4(14) y
O1 C2 C6 C5 168.2(18) y
O3 C2 C6 C5 -23.2(13) y
C31 C25 C6 N7 -44.7(8) y
C24 C25 C6 N7 -162.4(4) y
C30 C25 C6 N7 81.9(8) y
C31 C25 C6 C22 79.3(15) y
C24 C25 C6 C22 -38.4(14) y
C30 C25 C6 C22 -154.1(14) y
C31 C25 C6 C2 85.6(11) y
C24 C25 C6 C2 -32.1(11) y
C30 C25 C6 C2 -147.8(10) y
C31 C25 C6 C5 78(5) y
C24 C25 C6 C5 -39(4) y
C30 C25 C6 C5 -155(5) y
C20 C5 C6 N7 150.2(3) y
C21 C5 C6 N7 25.6(6) y
C4 C5 C6 N7 -93.5(4) y
C20 C5 C6 C22 -89.5(13) y
C21 C5 C6 C22 145.9(13) y
C4 C5 C6 C22 26.8(13) y
C20 C5 C6 C2 -83.5(9) y
C21 C5 C6 C2 151.9(9) y
C4 C5 C6 C2 32.8(9) y
C20 C5 C6 C25 90(5) y
C21 C5 C6 C25 -35(4) y
C4 C5 C6 C25 -154(5) y
C22 C6 N7 C8 82.1(9) y
C2 C6 N7 C8 73.3(6) y
C25 C6 N7 C8 -158.7(5) y
C5 C6 N7 C8 -167.5(3) y
C6 N7 C8 C9 68.60(12) y
C6 N7 C8 C19 -170.28(10) y
N7 C8 C9 C10 28.51(13) y
C19 C8 C9 C10 -91.66(13) y
N7 C8 C9 C18 -151.46(9) y
C19 C8 C9 C18 88.37(13) y
C18 C9 C10 C11 0.22(17) y
C8 C9 C10 C11 -179.75(10) y
C9 C10 C11 C12 -0.51(18) y
C10 C11 C12 C13 0.61(17) y
C11 C12 C13 C14 178.39(10) y
C11 C12 C13 C18 -0.44(16) y
C12 C13 C14 C15 -179.56(11) y
C18 C13 C14 C15 -0.73(16) y
C13 C14 C15 C16 -0.01(18) y
C14 C15 C16 C17 0.36(18) y
C15 C16 C17 C18 0.05(16) y
C16 C17 C18 C13 -0.77(15) y
C16 C17 C18 C9 179.01(10) y
C14 C13 C18 C17 1.10(14) y
C12 C13 C18 C17 179.95(10) y
C14 C13 C18 C9 -178.69(10) y
C12 C13 C18 C9 0.15(15) y
C10 C9 C18 C17 -179.83(10) y
C8 C9 C18 C17 0.14(15) y
C10 C9 C18 C13 -0.04(15) y
C8 C9 C18 C13 179.93(9) y
O31 C32 O33 C34 178.33(12) y
C36 C32 O33 C34 -0.51(14) y
C32 O33 C34 C35 -23.54(14) y
O33 C34 C35 C51 155.65(11) y
O33 C34 C35 C50 -79.89(14) y
O33 C34 C35 C36 36.37(12) y
O31 C32 C36 N37 -27.75(19) y
O33 C32 C36 N37 150.98(10) y
O31 C32 C36 C35 -154.78(13) y
O33 C32 C36 C35 23.95(12) y
C51 C35 C36 N37 77.07(13) y
C34 C35 C36 N37 -163.40(10) y
C50 C35 C36 N37 -48.46(14) y
C51 C35 C36 C32 -154.69(10) y
C34 C35 C36 C32 -35.16(11) y
C50 C35 C36 C32 79.78(12) y
C32 C36 N37 C38 68.56(13) y
C35 C36 N37 C38 -170.95(10) y
C36 N37 C38 C39 63.48(13) y
C36 N37 C38 C49 -175.78(11) y
N37 C38 C39 C40 46.27(15) y
C49 C38 C39 C40 -73.13(15) y
N37 C38 C39 C48 -135.15(11) y
C49 C38 C39 C48 105.44(13) y
C48 C39 C40 C41 0.98(17) y
C38 C39 C40 C41 179.58(11) y
C39 C40 C41 C42 0.43(17) y
C40 C41 C42 C43 -1.19(17) y
C41 C42 C43 C44 179.49(11) y
C41 C42 C43 C48 0.53(16) y
C42 C43 C44 C45 -179.87(11) y
C48 C43 C44 C45 -0.91(17) y
C43 C44 C45 C46 0.28(19) y
C44 C45 C46 C47 0.17(19) y
C45 C46 C47 C48 0.01(18) y
C46 C47 C48 C43 -0.63(16) y
C46 C47 C48 C39 178.50(11) y
C42 C43 C48 C47 -179.97(10) y
C44 C43 C48 C47 1.06(15) y
C42 C43 C48 C39 0.86(15) y
C44 C43 C48 C39 -178.12(10) y
C40 C39 C48 C47 179.28(10) y
C38 C39 C48 C47 0.70(16) y
C40 C39 C48 C43 -1.60(15) y
C38 C39 C48 C43 179.83(10) y
