#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/34/1513427.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_1513427
loop_
_publ_author_name
'Morin, Marie S. T.'
'Arndtsen, Bruce A.'
_publ_section_title
;
 Chiral phosphorus-based 1,3-dipoles: a modular approach to
 enantioselective 1,3-dipolar cycloaddition and polycyclic 2-pyrroline
 synthesis.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              1056
_journal_page_last               1059
_journal_paper_doi               10.1021/ol4035512
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration rmad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C20 H23 N O'
_chemical_formula_sum            'C20 H23 N O'
_chemical_formula_weight         293.39
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 113.102(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7825(2)
_cell_length_b                   5.8322(1)
_cell_length_c                   18.8095(2)
_cell_measurement_reflns_used    9279
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.80
_cell_measurement_theta_min      4.68
_cell_volume                     1592.51(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  (Bruker AXS, 2003)'
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.020
_diffrn_reflns_av_sigmaI/netI    0.0086
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            83998
_diffrn_reflns_theta_full        71.16
_diffrn_reflns_theta_max         71.16
_diffrn_reflns_theta_min         2.55
_exptl_absorpt_coefficient_mu    0.575
_exptl_absorpt_correction_T_max  0.9661
_exptl_absorpt_correction_T_min  0.8630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
'Flack, H.D. and Schwarzenbach, D. (1999), XXXX Friedel Pairs'
_refine_ls_abs_structure_Flack   0.09(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         6071
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0280
_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)+(0.0433P)²+0.2814P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0723
_reflns_number_gt                6057
_reflns_number_total             6071
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ol4035512_si_002.cif
_cod_data_source_block           arst38
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1513427
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
O1 O 0.80721(5) -0.05040(15) 0.43165(5) 0.02448(18) Uani 1 1 d .
N1 N 0.74059(6) 0.34596(17) 0.25898(5) 0.01785(19) Uani 1 1 d .
C101 C 0.66505(7) 0.50052(19) 0.25522(6) 0.0185(2) Uani 1 1 d .
H101 H 0.6856 0.6629 0.2556 0.022 Uiso 1 1 calc R
C102 C 0.65314(7) 0.4515(2) 0.33173(6) 0.0209(2) Uani 1 1 d .
H10A H 0.6453 0.5961 0.3561 0.025 Uiso 1 1 calc R
H10B H 0.5989 0.3525 0.3224 0.025 Uiso 1 1 calc R
C103 C 0.74271(8) 0.3281(2) 0.38351(6) 0.0196(2) Uani 1 1 d .
H103 H 0.7699 0.3996 0.4360 0.024 Uiso 1 1 calc R
C104 C 0.72448(8) 0.0754(2) 0.38881(7) 0.0227(2) Uani 1 1 d .
H10C H 0.6805 0.0565 0.4141 0.027 Uiso 1 1 calc R
H10D H 0.6956 0.0111 0.3360 0.027 Uiso 1 1 calc R
C105 C 0.87877(7) -0.0108(2) 0.40905(6) 0.0191(2) Uani 1 1 d .
C106 C 0.95171(8) -0.1663(2) 0.43686(6) 0.0216(2) Uani 1 1 d .
H106 H 0.9492 -0.2908 0.4685 0.026 Uiso 1 1 calc R
C107 C 1.02773(8) -0.1387(2) 0.41816(6) 0.0242(2) Uani 1 1 d .
H107 H 1.0767 -0.2468 0.4358 0.029 Uiso 1 1 calc R
C108 C 1.03229(8) 0.0473(2) 0.37359(7) 0.0260(3) Uani 1 1 d .
H108 H 1.0844 0.0674 0.3608 0.031 Uiso 1 1 calc R
C109 C 0.96050(8) 0.2030(2) 0.34798(6) 0.0232(2) Uani 1 1 d .
H109 H 0.9648 0.3315 0.3186 0.028 Uiso 1 1 calc R
C110 C 0.88153(7) 0.1771(2) 0.36406(6) 0.0182(2) Uani 1 1 d .
C111 C 0.80654(7) 0.3569(2) 0.34045(6) 0.0176(2) Uani 1 1 d .
H111 H 0.8353 0.5126 0.3514 0.021 Uiso 1 1 calc R
C112 C 0.77866(8) 0.3940(2) 0.20090(6) 0.0226(2) Uani 1 1 d .
H11A H 0.7285 0.3770 0.1491 0.027 Uiso 1 1 calc R
H11B H 0.8254 0.2753 0.2055 0.027 Uiso 1 1 calc R
C113 C 0.82311(8) 0.6292(2) 0.20457(7) 0.0275(3) Uani 1 1 d .
H11C H 0.7773 0.7495 0.1981 0.041 Uiso 1 1 calc R
H11D H 0.8459 0.6412 0.1632 0.041 Uiso 1 1 calc R
H11E H 0.8746 0.6475 0.2548 0.041 Uiso 1 1 calc R
C114 C 0.57966(7) 0.4600(2) 0.18231(6) 0.0184(2) Uani 1 1 d .
C115 C 0.53561(8) 0.2474(2) 0.16893(7) 0.0211(2) Uani 1 1 d .
H115 H 0.5604 0.1265 0.2051 0.025 Uiso 1 1 calc R
C116 C 0.45628(8) 0.2105(2) 0.10365(7) 0.0227(2) Uani 1 1 d .
H116 H 0.4271 0.0648 0.0958 0.027 Uiso 1 1 calc R
C117 C 0.41835(8) 0.3841(2) 0.04893(6) 0.0222(2) Uani 1 1 d .
C118 C 0.46386(8) 0.5931(2) 0.06118(7) 0.0226(2) Uani 1 1 d .
H118 H 0.4406 0.7120 0.0240 0.027 Uiso 1 1 calc R
C119 C 0.54341(7) 0.6307(2) 0.12740(6) 0.0202(2) Uani 1 1 d .
H119 H 0.5732 0.7756 0.1350 0.024 Uiso 1 1 calc R
C120 C 0.32959(8) 0.3449(3) -0.02028(7) 0.0301(3) Uani 1 1 d .
H12A H 0.2773 0.3647 -0.0051 0.045 Uiso 1 1 calc R
H12B H 0.3290 0.1889 -0.0398 0.045 Uiso 1 1 calc R
H12C H 0.3248 0.4556 -0.0609 0.045 Uiso 1 1 calc R
O2 O 0.48126(5) 1.01435(15) 0.34788(5) 0.02233(17) Uani 1 1 d .
N2 N 0.25018(6) 0.72711(18) 0.24292(5) 0.0204(2) Uani 1 1 d .
C201 C 0.25844(8) 0.5256(2) 0.19869(7) 0.0221(2) Uani 1 1 d .
H201 H 0.2361 0.3864 0.2171 0.027 Uiso 1 1 calc R
C202 C 0.36369(8) 0.5063(2) 0.22174(7) 0.0242(2) Uani 1 1 d .
H20A H 0.3837 0.3442 0.2305 0.029 Uiso 1 1 calc R
H20B H 0.3814 0.5707 0.1808 0.029 Uiso 1 1 calc R
C203 C 0.40718(8) 0.6453(2) 0.29674(6) 0.0212(2) Uani 1 1 d .
H203 H 0.4553 0.5539 0.3380 0.025 Uiso 1 1 calc R
C204 C 0.44670(8) 0.8671(2) 0.28120(6) 0.0220(2) Uani 1 1 d .
H20C H 0.4973 0.8312 0.2644 0.026 Uiso 1 1 calc R
H20D H 0.3983 0.9495 0.2384 0.026 Uiso 1 1 calc R
C205 C 0.42199(7) 1.0478(2) 0.38436(6) 0.0194(2) Uani 1 1 d .
C206 C 0.44561(7) 1.2234(2) 0.43906(6) 0.0212(2) Uani 1 1 d .
H206 H 0.5002 1.3099 0.4495 0.025 Uiso 1 1 calc R
C207 C 0.38955(8) 1.2715(2) 0.47809(6) 0.0222(2) Uani 1 1 d .
H207 H 0.4048 1.3940 0.5142 0.027 Uiso 1 1 calc R
C208 C 0.31084(8) 1.1409(2) 0.46465(6) 0.0223(2) Uani 1 1 d .
H208 H 0.2713 1.1762 0.4903 0.027 Uiso 1 1 calc R
C209 C 0.29109(7) 0.9591(2) 0.41340(6) 0.0213(2) Uani 1 1 d .
H209 H 0.2393 0.8650 0.4066 0.026 Uiso 1 1 calc R
C210 C 0.34487(7) 0.90922(19) 0.37122(6) 0.0186(2) Uani 1 1 d .
C211 C 0.32610(7) 0.7015(2) 0.31942(6) 0.0193(2) Uani 1 1 d .
H211 H 0.3134 0.5666 0.3466 0.023 Uiso 1 1 calc R
C212 C 0.15804(8) 0.7601(2) 0.24238(7) 0.0277(3) Uani 1 1 d .
H21A H 0.1144 0.7795 0.1880 0.033 Uiso 1 1 calc R
H21B H 0.1582 0.9053 0.2697 0.033 Uiso 1 1 calc R
C213 C 0.12068(9) 0.5707(3) 0.27860(9) 0.0389(3) Uani 1 1 d .
H21C H 0.1192 0.4253 0.2520 0.058 Uiso 1 1 calc R
H21D H 0.0582 0.6106 0.2735 0.058 Uiso 1 1 calc R
H21E H 0.1607 0.5552 0.3335 0.058 Uiso 1 1 calc R
C214 C 0.20267(8) 0.5566(2) 0.11301(7) 0.0222(2) Uani 1 1 d .
C215 C 0.21145(9) 0.7539(2) 0.07481(7) 0.0265(3) Uani 1 1 d .
H215 H 0.2532 0.8705 0.1028 0.032 Uiso 1 1 calc R
C216 C 0.15994(9) 0.7822(2) -0.00365(7) 0.0271(3) Uani 1 1 d .
H216 H 0.1669 0.9186 -0.0284 0.033 Uiso 1 1 calc R
C217 C 0.09836(8) 0.6154(2) -0.04676(7) 0.0252(2) Uani 1 1 d .
C218 C 0.08918(8) 0.4186(2) -0.00873(7) 0.0279(3) Uani 1 1 d .
H218 H 0.0471 0.3026 -0.0368 0.034 Uiso 1 1 calc R
C219 C 0.14093(8) 0.3890(2) 0.07016(7) 0.0259(3) Uani 1 1 d .
H219 H 0.1339 0.2527 0.0950 0.031 Uiso 1 1 calc R
C220 C 0.04350(9) 0.6462(3) -0.13215(7) 0.0321(3) Uani 1 1 d .
H22A H 0.0485 0.8055 -0.1466 0.048 Uiso 1 1 calc R
H22B H -0.0213 0.6092 -0.1443 0.048 Uiso 1 1 calc R
H22C H 0.0676 0.5437 -0.1611 0.048 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
C105 O1 C104 114.64(8) y
C112 N1 C101 114.06(9) y
C112 N1 C111 115.91(8) y
C101 N1 C111 104.52(8) y
N1 C101 C114 111.28(8) y
N1 C101 C102 103.49(9) y
C114 C101 C102 114.98(9) y
N1 C101 H101 109.0 ?
C114 C101 H101 109.0 ?
C102 C101 H101 109.0 ?
C103 C102 C101 104.91(9) y
C103 C102 H10A 110.8 ?
C101 C102 H10A 110.8 ?
C103 C102 H10B 110.8 ?
C101 C102 H10B 110.8 ?
H10A C102 H10B 108.8 ?
C104 C103 C111 108.88(9) y
C104 C103 C102 110.18(10) y
C111 C103 C102 104.19(9) y
C104 C103 H103 111.1 ?
C111 C103 H103 111.1 ?
C102 C103 H103 111.1 ?
O1 C104 C103 112.33(9) y
O1 C104 H10C 109.1 ?
C103 C104 H10C 109.1 ?
O1 C104 H10D 109.1 ?
C103 C104 H10D 109.1 ?
H10C C104 H10D 107.9 ?
O1 C105 C110 123.02(10) y
O1 C105 C106 115.59(10) y
C110 C105 C106 121.33(10) y
C107 C106 C105 119.88(11) y
C107 C106 H106 120.1 ?
C105 C106 H106 120.1 ?
C106 C107 C108 119.90(11) y
C106 C107 H107 120.0 ?
C108 C107 H107 120.0 ?
C109 C108 C107 119.54(11) y
C109 C108 H108 120.2 ?
C107 C108 H108 120.2 ?
C108 C109 C110 122.07(11) y
C108 C109 H109 119.0 ?
C110 C109 H109 119.0 ?
C105 C110 C109 117.23(10) y
C105 C110 C111 121.04(9) y
C109 C110 C111 121.47(10) y
N1 C111 C110 115.24(9) y
N1 C111 C103 101.67(8) y
C110 C111 C103 111.77(9) y
N1 C111 H111 109.3 ?
C110 C111 H111 109.3 ?
C103 C111 H111 109.3 ?
N1 C112 C113 116.91(10) y
N1 C112 H11A 108.1 ?
C113 C112 H11A 108.1 ?
N1 C112 H11B 108.1 ?
C113 C112 H11B 108.1 ?
H11A C112 H11B 107.3 ?
C112 C113 H11C 109.5 ?
C112 C113 H11D 109.5 ?
H11C C113 H11D 109.5 ?
C112 C113 H11E 109.5 ?
H11C C113 H11E 109.5 ?
H11D C113 H11E 109.5 ?
C119 C114 C115 118.25(10) y
C119 C114 C101 121.45(10) y
C115 C114 C101 120.30(10) y
C116 C115 C114 120.76(11) y
C116 C115 H115 119.6 ?
C114 C115 H115 119.6 ?
C115 C116 C117 121.12(11) y
C115 C116 H116 119.4 ?
C117 C116 H116 119.4 ?
C118 C117 C116 117.99(10) y
C118 C117 C120 121.41(11) y
C116 C117 C120 120.59(12) y
C117 C118 C119 120.80(11) y
C117 C118 H118 119.6 ?
C119 C118 H118 119.6 ?
C114 C119 C118 121.02(11) y
C114 C119 H119 119.5 ?
C118 C119 H119 119.5 ?
C117 C120 H12A 109.5 ?
C117 C120 H12B 109.5 ?
H12A C120 H12B 109.5 ?
C117 C120 H12C 109.5 ?
H12A C120 H12C 109.5 ?
H12B C120 H12C 109.5 ?
C205 O2 C204 114.87(9) y
C212 N2 C211 116.41(9) y
C212 N2 C201 114.10(9) y
C211 N2 C201 104.58(9) y
N2 C201 C214 111.22(9) y
N2 C201 C202 102.86(9) y
C214 C201 C202 114.77(9) y
N2 C201 H201 109.3 ?
C214 C201 H201 109.3 ?
C202 C201 H201 109.3 ?
C203 C202 C201 105.24(9) y
C203 C202 H20A 110.7 ?
C201 C202 H20A 110.7 ?
C203 C202 H20B 110.7 ?
C201 C202 H20B 110.7 ?
H20A C202 H20B 108.8 ?
C204 C203 C211 108.84(9) y
C204 C203 C202 110.08(9) y
C211 C203 C202 104.31(9) y
C204 C203 H203 111.1 ?
C211 C203 H203 111.1 ?
C202 C203 H203 111.1 ?
O2 C204 C203 112.69(9) y
O2 C204 H20C 109.1 ?
C203 C204 H20C 109.1 ?
O2 C204 H20D 109.1 ?
C203 C204 H20D 109.1 ?
H20C C204 H20D 107.8 ?
O2 C205 C206 115.82(10) y
O2 C205 C210 123.02(10) y
C206 C205 C210 121.10(10) y
C207 C206 C205 119.95(10) y
C207 C206 H206 120.0 ?
C205 C206 H206 120.0 ?
C206 C207 C208 120.26(11) y
C206 C207 H207 119.9 ?
C208 C207 H207 119.9 ?
C209 C208 C207 119.10(10) y
C209 C208 H208 120.4 ?
C207 C208 H208 120.4 ?
C208 C209 C210 122.18(10) y
C208 C209 H209 118.9 ?
C210 C209 H209 118.9 ?
C205 C210 C209 117.26(10) y
C205 C210 C211 120.96(10) y
C209 C210 C211 121.53(10) y
N2 C211 C210 115.27(9) y
N2 C211 C203 101.37(8) y
C210 C211 C203 112.14(9) y
N2 C211 H211 109.2 ?
C210 C211 H211 109.2 ?
C203 C211 H211 109.2 ?
N2 C212 C213 117.21(12) y
N2 C212 H21A 108.0 ?
C213 C212 H21A 108.0 ?
N2 C212 H21B 108.0 ?
C213 C212 H21B 108.0 ?
H21A C212 H21B 107.2 ?
C212 C213 H21C 109.5 ?
C212 C213 H21D 109.5 ?
H21C C213 H21D 109.5 ?
C212 C213 H21E 109.5 ?
H21C C213 H21E 109.5 ?
H21D C213 H21E 109.5 ?
C215 C214 C219 118.05(11) y
C215 C214 C201 120.97(11) y
C219 C214 C201 120.98(11) y
C216 C215 C214 120.82(12) y
C216 C215 H215 119.6 ?
C214 C215 H215 119.6 ?
C215 C216 C217 121.41(12) y
C215 C216 H216 119.3 ?
C217 C216 H216 119.3 ?
C216 C217 C218 117.92(11) y
C216 C217 C220 121.12(12) y
C218 C217 C220 120.96(11) y
C217 C218 C219 120.91(11) y
C217 C218 H218 119.5 ?
C219 C218 H218 119.5 ?
C214 C219 C218 120.89(12) y
C214 C219 H219 119.6 ?
C218 C219 H219 119.6 ?
C217 C220 H22A 109.5 ?
C217 C220 H22B 109.5 ?
H22A C220 H22B 109.5 ?
C217 C220 H22C 109.5 ?
H22A C220 H22C 109.5 ?
H22B C220 H22C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C105 1.3734(13) y
O1 C104 1.4378(14) y
N1 C112 1.4656(14) y
N1 C101 1.4741(14) y
N1 C111 1.4778(13) y
C101 C114 1.5174(14) y
C101 C102 1.5493(15) y
C101 H101 1.0000 ?
C102 C103 1.5441(15) y
C102 H10a 0.9900 ?
C102 H10b 0.9900 ?
C103 C104 1.5123(17) y
C103 C111 1.5294(15) y
C103 H103 1.0000 ?
C104 H10c 0.9900 ?
C104 H10d 0.9900 ?
C105 C110 1.3953(16) y
C105 C106 1.3962(16) y
C106 C107 1.3856(17) y
C106 H106 0.9500 ?
C107 C108 1.3904(19) y
C107 H107 0.9500 ?
C108 C109 1.3826(17) y
C108 H108 0.9500 ?
C109 C110 1.4012(15) y
C109 H109 0.9500 ?
C110 C111 1.5117(15) y
C111 H111 1.0000 ?
C112 C113 1.5299(18) y
C112 H11a 0.9900 ?
C112 H11b 0.9900 ?
C113 H11c 0.9800 ?
C113 H11d 0.9800 ?
C113 H11e 0.9800 ?
C114 C119 1.3864(16) y
C114 C115 1.3952(16) y
C115 C116 1.3839(16) y
C115 H115 0.9500 ?
C116 C117 1.3999(17) y
C116 H116 0.9500 ?
C117 C118 1.3874(18) y
C117 C120 1.5094(15) y
C118 C119 1.3961(16) y
C118 H118 0.9500 ?
C119 H119 0.9500 ?
C120 H12a 0.9800 ?
C120 H12b 0.9800 ?
C120 H12c 0.9800 ?
O2 C205 1.3738(13) y
O2 C204 1.4391(15) y
N2 C212 1.4629(14) y
N2 C211 1.4750(13) y
N2 C201 1.4751(15) y
C201 C214 1.5137(16) y
C201 C202 1.5475(16) y
C201 H201 1.0000 ?
C202 C203 1.5357(16) y
C202 H20a 0.9900 ?
C202 H20b 0.9900 ?
C203 C204 1.5136(17) y
C203 C211 1.5347(14) y
C203 H203 1.0000 ?
C204 H20c 0.9900 ?
C204 H20d 0.9900 ?
C205 C206 1.3948(17) y
C205 C210 1.4000(16) y
C206 C207 1.3821(16) y
C206 H206 0.9500 ?
C207 C208 1.3930(17) y
C207 H207 0.9500 ?
C208 C209 1.3840(17) y
C208 H208 0.9500 ?
C209 C210 1.4012(15) y
C209 H209 0.9500 ?
C210 C211 1.5095(15) y
C211 H211 1.0000 ?
C212 C213 1.532(2) y
C212 H21a 0.9900 ?
C212 H21b 0.9900 ?
C213 H21c 0.9800 ?
C213 H21d 0.9800 ?
C213 H21e 0.9800 ?
C214 C215 1.3917(18) y
C214 C219 1.3923(17) y
C215 C216 1.3873(17) y
C215 H215 0.9500 ?
C216 C217 1.3892(18) y
C216 H216 0.9500 ?
C217 C218 1.3898(19) y
C217 C220 1.5068(16) y
C218 C219 1.3956(17) y
C218 H218 0.9500 ?
C219 H219 0.9500 ?
C220 H22a 0.9800 ?
C220 H22b 0.9800 ?
C220 H22c 0.9800 ?
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
C112 N1 C101 C114 68.39(12) y
C111 N1 C101 C114 -164.03(9) y
C112 N1 C101 C102 -167.59(9) y
C111 N1 C101 C102 -40.01(10) y
N1 C101 C102 C103 17.08(11) y
C114 C101 C102 C103 138.64(10) y
C101 C102 C103 C104 -105.86(10) y
C101 C102 C103 C111 10.78(11) y
C105 O1 C104 C103 -49.72(13) y
C111 C103 C104 O1 61.90(12) y
C102 C103 C104 O1 175.58(8) y
C104 O1 C105 C110 16.63(15) y
C104 O1 C105 C106 -166.04(10) y
O1 C105 C106 C107 -179.05(10) y
C110 C105 C106 C107 -1.67(16) y
C105 C106 C107 C108 1.82(17) y
C106 C107 C108 C109 -0.30(18) y
C107 C108 C109 C110 -1.43(18) y
O1 C105 C110 C109 177.18(10) y
C106 C105 C110 C109 0.00(15) y
O1 C105 C110 C111 3.00(16) y
C106 C105 C110 C111 -174.18(10) y
C108 C109 C110 C105 1.56(16) y
C108 C109 C110 C111 175.72(11) y
C112 N1 C111 C110 -65.50(13) y
C101 N1 C111 C110 168.06(9) y
C112 N1 C111 C103 173.43(10) y
C101 N1 C111 C103 46.99(10) y
C105 C110 C111 N1 -104.84(11) y
C109 C110 C111 N1 81.23(13) y
C105 C110 C111 C103 10.57(14) y
C109 C110 C111 C103 -163.36(10) y
C104 C103 C111 N1 82.95(11) y
C102 C103 C111 N1 -34.60(11) y
C104 C103 C111 C110 -40.51(12) y
C102 C103 C111 C110 -158.05(9) y
C101 N1 C112 C113 61.97(12) y
C111 N1 C112 C113 -59.51(13) y
N1 C101 C114 C119 -118.17(11) y
C102 C101 C114 C119 124.61(11) y
N1 C101 C114 C115 61.70(13) y
C102 C101 C114 C115 -55.53(13) y
C119 C114 C115 C116 -1.89(16) y
C101 C114 C115 C116 178.24(10) y
C114 C115 C116 C117 0.53(17) y
C115 C116 C117 C118 1.44(16) y
C115 C116 C117 C120 -177.38(10) y
C116 C117 C118 C119 -2.03(16) y
C120 C117 C118 C119 176.78(10) y
C115 C114 C119 C118 1.30(16) y
C101 C114 C119 C118 -178.84(10) y
C117 C118 C119 C114 0.68(16) y
C212 N2 C201 C214 67.03(13) y
C211 N2 C201 C214 -164.67(9) y
C212 N2 C201 C202 -169.64(10) y
C211 N2 C201 C202 -41.33(11) y
N2 C201 C202 C203 18.77(12) y
C214 C201 C202 C203 139.70(10) y
C201 C202 C203 C204 -107.46(10) y
C201 C202 C203 C211 9.16(12) y
C205 O2 C204 C203 -48.91(13) y
C211 C203 C204 O2 61.10(12) y
C202 C203 C204 O2 174.85(9) y
C204 O2 C205 C206 -167.73(10) y
C204 O2 C205 C210 15.37(15) y
O2 C205 C206 C207 179.27(10) y
C210 C205 C206 C207 -3.77(16) y
C205 C206 C207 C208 1.85(17) y
C206 C207 C208 C209 1.75(17) y
C207 C208 C209 C210 -3.59(17) y
O2 C205 C210 C209 178.73(10) y
C206 C205 C210 C209 1.99(15) y
O2 C205 C210 C211 4.39(16) y
C206 C205 C210 C211 -172.34(10) y
C208 C209 C210 C205 1.71(16) y
C208 C209 C210 C211 176.01(10) y
C212 N2 C211 C210 -64.56(13) y
C201 N2 C211 C210 168.55(9) y
C212 N2 C211 C203 174.11(11) y
C201 N2 C211 C203 47.22(10) y
C205 C210 C211 N2 -105.81(11) y
C209 C210 C211 N2 80.10(12) y
C205 C210 C211 C203 9.49(14) y
C209 C210 C211 C203 -164.60(10) y
C204 C203 C211 N2 83.80(10) y
C202 C203 C211 N2 -33.67(11) y
C204 C203 C211 C210 -39.69(12) y
C202 C203 C211 C210 -157.17(9) y
C211 N2 C212 C213 -59.58(14) y
C201 N2 C212 C213 62.43(13) y
N2 C201 C214 C215 50.84(14) y
C202 C201 C214 C215 -65.39(15) y
N2 C201 C214 C219 -129.01(11) y
C202 C201 C214 C219 114.76(12) y
C219 C214 C215 C216 0.13(18) y
C201 C214 C215 C216 -179.73(11) y
C214 C215 C216 C217 -0.25(19) y
C215 C216 C217 C218 0.47(18) y
C215 C216 C217 C220 -179.25(11) y
C216 C217 C218 C219 -0.57(17) y
C220 C217 C218 C219 179.14(12) y
C215 C214 C219 C218 -0.23(17) y
C201 C214 C219 C218 179.62(11) y
C217 C218 C219 C214 0.47(18) y
