#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/16/2221687.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2221687
loop_
_publ_author_name
'Jin, Jia'
'Xue, Si-Jia'
'Li, Xue-Fei'
'Fang, Zhi-Kun'
_publ_section_title
;
 (+)-[1-(4-Methoxybenzyl)pyrrolidin-2-yl]diphenylmethanol
;
_journal_coeditor_code           HB2936
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1035
_journal_paper_doi               10.1107/S1600536809011817
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C25 H27 N O2'
_chemical_formula_moiety         'C25 H27 N O2'
_chemical_formula_sum            'C25 H27 N O2'
_chemical_formula_weight         373.48
_chemical_melting_point          391
_chemical_name_common            f080808
_chemical_name_systematic
;
(+)-[1-(4-Methoxybenzyl)pyrrolidin-2-yl]diphenylmethanol
;
_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                90.00
_cell_angle_beta                 97.715(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   33.131(4)
_cell_length_b                   5.9916(7)
_cell_length_c                   21.472(3)
_cell_measurement_reflns_used    1185
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      17.04
_cell_measurement_theta_min      2.48
_cell_volume                     4223.8(9)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1073
_diffrn_reflns_av_sigmaI/netI    0.0915
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20497
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.160
_refine_ls_abs_structure_details none
_refine_ls_extinction_coef       0.0016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.932
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     536
_refine_ls_number_reflns         4093
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      0.932
_refine_ls_R_factor_all          0.1567
_refine_ls_R_factor_gt           0.0673
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0935P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1498
_refine_ls_wR_factor_ref         0.1790
_reflns_number_gt                2040
_reflns_number_total             4093
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2936.cif
_cod_data_source_block           I
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2221687
_cod_database_fobs_code          2221687
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.08941(17) 0.3509(11) 0.3865(3) 0.0601(17) Uani d . 1 . .
C C2 0.0964(2) 0.1590(16) 0.4202(3) 0.099(2) Uani d . 1 . .
H H2 0.1087 0.0383 0.4030 0.119 Uiso calc R 1 . .
C C3 0.0852(3) 0.143(2) 0.4800(4) 0.122(3) Uani d . 1 . .
H H3 0.0911 0.0115 0.5026 0.146 Uiso calc R 1 . .
C C4 0.0666(3) 0.303(2) 0.5063(4) 0.112(3) Uani d . 1 . .
H H4 0.0585 0.2841 0.5458 0.135 Uiso calc R 1 . .
C C5 0.0596(3) 0.4983(19) 0.4745(3) 0.114(3) Uani d . 1 . .
H H5 0.0472 0.6161 0.4928 0.136 Uiso calc R 1 . .
C C6 0.0709(2) 0.5235(14) 0.4141(3) 0.097(3) Uani d . 1 . .
H H6 0.0659 0.6577 0.3927 0.117 Uiso calc R 1 . .
C C7 0.04379(19) 0.6188(11) 0.2672(3) 0.0637(17) Uani d . 1 . .
H H7 0.0527 0.7343 0.2945 0.076 Uiso calc R 1 . .
C C8 0.0106(2) 0.6517(14) 0.2239(3) 0.0721(18) Uani d . 1 . .
H H8 -0.0030 0.7877 0.2226 0.087 Uiso calc R 1 . .
C C9 -0.0031(2) 0.4887(18) 0.1823(3) 0.088(2) Uani d . 1 . .
H H9 -0.0257 0.5126 0.1523 0.106 Uiso calc R 1 . .
C C10 0.0170(2) 0.2886(14) 0.1852(4) 0.090(2) Uani d . 1 . .
H H10 0.0079 0.1755 0.1571 0.109 Uiso calc R 1 . .
C C11 0.0506(2) 0.2531(12) 0.2294(3) 0.0760(19) Uani d . 1 . .
H H11 0.0640 0.1163 0.2305 0.091 Uiso calc R 1 . .
C C12 0.06482(16) 0.4176(10) 0.2720(2) 0.0485(15) Uani d . 1 . .
C C13 0.10208(18) 0.3747(12) 0.3204(3) 0.0633(17) Uani d . 1 B .
C C14 0.13520(17) 0.5563(14) 0.3190(2) 0.073(2) Uani d . 1 . .
H H14 0.1237 0.7068 0.3201 0.087 Uiso calc R 1 A 1
C C17 0.2001(3) 0.488(5) 0.2787(6) 0.099(7) Uani d PD 0.63(3) B 1
H H17A 0.2148 0.6269 0.2761 0.119 Uiso calc PR 0.63(3) B 1
H H17B 0.2100 0.3793 0.2510 0.119 Uiso calc PR 0.63(3) B 1
C C16 0.2048(4) 0.401(5) 0.3470(5) 0.091(7) Uani d PD 0.63(3) B 1
H H16A 0.2019 0.2403 0.3482 0.109 Uiso calc PR 0.63(3) B 1
H H16B 0.2310 0.4428 0.3698 0.109 Uiso calc PR 0.63(3) B 1
C C15 0.1699(8) 0.519(5) 0.3738(15) 0.077(8) Uani d PD 0.63(3) B 1
H H15A 0.1791 0.6605 0.3923 0.093 Uiso calc PR 0.63(3) B 1
H H15B 0.1604 0.4271 0.4061 0.093 Uiso calc PR 0.63(3) B 1
C C15' 0.1681(16) 0.600(12) 0.379(3) 0.117(17) Uani d PD 0.37(3) B 2
H H15C 0.1632 0.7412 0.3986 0.140 Uiso calc PR 0.37(3) B 2
H H15D 0.1681 0.4811 0.4093 0.140 Uiso calc PR 0.37(3) B 2
C C16' 0.2083(9) 0.605(11) 0.3506(11) 0.134(16) Uani d PD 0.37(3) B 2
H H16C 0.2252 0.7290 0.3676 0.161 Uiso calc PR 0.37(3) B 2
H H16D 0.2233 0.4673 0.3597 0.161 Uiso calc PR 0.37(3) B 2
C C17' 0.1961(6) 0.633(6) 0.2798(10) 0.089(10) Uani d PD 0.37(3) B 2
H H17C 0.1942 0.7899 0.2690 0.107 Uiso calc PR 0.37(3) B 2
H H17D 0.2163 0.5642 0.2572 0.107 Uiso calc PR 0.37(3) B 2
C C18 0.14033(19) 0.6485(12) 0.2070(3) 0.0732(19) Uani d . 1 . .
H H18A 0.1475 0.8043 0.2138 0.088 Uiso calc R 1 B .
H H18B 0.1108 0.6383 0.2003 0.088 Uiso calc R 1 . .
C C19 0.15663(18) 0.5684(12) 0.1493(3) 0.0616(17) Uani d . 1 B .
C C20 0.18472(19) 0.6911(13) 0.1207(3) 0.0732(19) Uani d . 1 . .
H H20 0.1933 0.8296 0.1369 0.088 Uiso calc R 1 B .
C C21 0.2001(2) 0.6082(14) 0.0680(3) 0.077(2) Uani d . 1 B .
H H21 0.2196 0.6895 0.0505 0.092 Uiso calc R 1 . .
C C22 0.1868(2) 0.4085(14) 0.0416(3) 0.0696(19) Uani d . 1 . .
C C23 0.15938(19) 0.2875(12) 0.0687(3) 0.0729(18) Uani d . 1 B .
H H23 0.1500 0.1518 0.0514 0.087 Uiso calc R 1 . .
C C24 0.14537(19) 0.3664(13) 0.1223(3) 0.0725(19) Uani d . 1 . .
H H24 0.1274 0.2779 0.1412 0.087 Uiso calc R 1 B .
C C25 0.1898(2) 0.1469(16) -0.0416(3) 0.110(3) Uani d . 1 . .
H H25A 0.1958 0.0253 -0.0128 0.165 Uiso calc R 1 B .
H H25B 0.2034 0.1238 -0.0778 0.165 Uiso calc R 1 . .
H H25C 0.1609 0.1544 -0.0545 0.165 Uiso calc R 1 . .
C C26 0.33222(18) 0.4931(11) 0.3688(3) 0.0618(16) Uani d . 1 . .
C C27 0.3166(2) 0.6886(14) 0.3858(4) 0.097(2) Uani d . 1 . .
H H27 0.3166 0.8109 0.3592 0.117 Uiso calc R 1 . .
C C28 0.3004(3) 0.7125(19) 0.4421(5) 0.130(4) Uani d . 1 . .
H H28 0.2915 0.8520 0.4534 0.156 Uiso calc R 1 . .
C C29 0.2977(3) 0.545(2) 0.4790(4) 0.117(3) Uani d . 1 . .
H H29 0.2848 0.5598 0.5146 0.140 Uiso calc R 1 . .
C C30 0.3142(3) 0.343(2) 0.4651(4) 0.115(3) Uani d . 1 . .
H H30 0.3142 0.2237 0.4928 0.138 Uiso calc R 1 . .
C C31 0.3311(2) 0.3178(14) 0.4090(3) 0.093(2) Uani d . 1 . .
H H31 0.3416 0.1803 0.3991 0.112 Uiso calc R 1 . .
C C32 0.39796(18) 0.4804(10) 0.3256(2) 0.0550(15) Uani d . 1 . .
C C33 0.4203(2) 0.3095(12) 0.3570(3) 0.0680(18) Uani d . 1 . .
H H33 0.4070 0.1805 0.3670 0.082 Uiso calc R 1 . .
C C34 0.4615(2) 0.3257(13) 0.3735(3) 0.0731(19) Uani d . 1 . .
H H34 0.4756 0.2096 0.3953 0.088 Uiso calc R 1 . .
C C35 0.4820(2) 0.5112(17) 0.3582(3) 0.085(2) Uani d . 1 . .
H H35 0.5101 0.5197 0.3689 0.102 Uiso calc R 1 . .
C C36 0.4613(2) 0.6840(14) 0.3273(3) 0.079(2) Uani d . 1 . .
H H36 0.4754 0.8106 0.3175 0.094 Uiso calc R 1 . .
C C37 0.4193(2) 0.6723(11) 0.3103(3) 0.0661(18) Uani d . 1 . .
H H37 0.4053 0.7902 0.2890 0.079 Uiso calc R 1 . .
C C38 0.35166(18) 0.4709(10) 0.3084(3) 0.0587(16) Uani d . 1 . .
C C39 0.33731(17) 0.2594(11) 0.2707(2) 0.0595(16) Uani d . 1 . .
H H39 0.3512 0.1278 0.2904 0.071 Uiso calc R 1 . .
C C40 0.29109(17) 0.2231(13) 0.2623(3) 0.075(2) Uani d . 1 . .
H H40A 0.2846 0.0794 0.2793 0.090 Uiso calc R 1 . .
H H40B 0.2779 0.3390 0.2839 0.090 Uiso calc R 1 . .
C C41 0.2770(2) 0.232(2) 0.1931(3) 0.126(4) Uani d . 1 . .
H H41A 0.2561 0.1207 0.1811 0.151 Uiso calc R 1 . .
H H41B 0.2661 0.3781 0.1808 0.151 Uiso calc R 1 . .
C C42 0.3128(2) 0.1855(15) 0.1642(3) 0.093(2) Uani d . 1 . .
H H42A 0.3104 0.2513 0.1226 0.111 Uiso calc R 1 . .
H H42B 0.3166 0.0258 0.1605 0.111 Uiso calc R 1 . .
C C43 0.38595(19) 0.1928(12) 0.1945(2) 0.0728(19) Uani d . 1 . .
H H43A 0.3843 0.0312 0.1946 0.087 Uiso calc R 1 . .
H H43B 0.4064 0.2372 0.2289 0.087 Uiso calc R 1 . .
C C44 0.39916(18) 0.2683(12) 0.1334(3) 0.0614(16) Uani d . 1 . .
C C45 0.3946(2) 0.1367(12) 0.0805(3) 0.0738(19) Uani d . 1 . .
H H45 0.3817 -0.0006 0.0819 0.089 Uiso calc R 1 . .
C C46 0.4086(2) 0.2006(15) 0.0252(3) 0.087(2) Uani d . 1 . .
H H46 0.4057 0.1063 -0.0095 0.105 Uiso calc R 1 . .
C C47 0.4267(2) 0.4038(14) 0.0225(3) 0.075(2) Uani d . 1 . .
C C48 0.4315(2) 0.5416(13) 0.0744(3) 0.081(2) Uani d . 1 . .
H H48 0.4440 0.6801 0.0732 0.097 Uiso calc R 1 . .
C C49 0.4172(2) 0.4680(13) 0.1279(3) 0.075(2) Uani d . 1 . .
H H49 0.4201 0.5619 0.1627 0.090 Uiso calc R 1 . .
C C50 0.4464(3) 0.326(2) -0.0772(4) 0.193(6) Uani d . 1 . .
H H50A 0.4671 0.2198 -0.0620 0.289 Uiso calc R 1 . .
H H50B 0.4540 0.4015 -0.1132 0.289 Uiso calc R 1 . .
H H50C 0.4210 0.2487 -0.0888 0.289 Uiso calc R 1 . .
N N1 0.15568(14) 0.5227(11) 0.2625(2) 0.0742(16) Uani d D 1 B .
N N2 0.34699(14) 0.2840(9) 0.20507(19) 0.0600(13) Uani d . 1 . .
O O1 0.12066(13) 0.1661(8) 0.30748(19) 0.0831(14) Uani d . 1 . .
H H1 0.1278 0.1705 0.2724 0.125 Uiso calc R 1 B .
O O2 0.20340(14) 0.3502(10) -0.0118(2) 0.0925(15) Uani d . 1 B .
O O3 0.33741(13) 0.6575(7) 0.26944(19) 0.0773(13) Uani d . 1 . .
H H3A 0.3482 0.6553 0.2372 0.116 Uiso calc R 1 . .
O O4 0.44186(16) 0.4827(12) -0.0294(2) 0.1126(19) Uani d . 1 . .
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 117.3(6) ?
C2 C1 C13 . . 121.3(6) ?
C6 C1 C13 . . 121.4(6) ?
C1 C2 C3 . . 120.3(9) ?
C1 C2 H2 . . 119.9 ?
C3 C2 H2 . . 119.9 ?
C4 C3 C2 . . 123.1(9) ?
C4 C3 H3 . . 118.4 ?
C2 C3 H3 . . 118.4 ?
C3 C4 C5 . . 118.3(8) ?
C3 C4 H4 . . 120.9 ?
C5 C4 H4 . . 120.9 ?
C4 C5 C6 . . 120.5(9) ?
C4 C5 H5 . . 119.7 ?
C6 C5 H5 . . 119.7 ?
C1 C6 C5 . . 120.4(8) ?
C1 C6 H6 . . 119.8 ?
C5 C6 H6 . . 119.8 ?
C8 C7 C12 . . 122.0(6) ?
C8 C7 H7 . . 119.0 ?
C12 C7 H7 . . 119.0 ?
C7 C8 C9 . . 120.9(7) ?
C7 C8 H8 . . 119.5 ?
C9 C8 H8 . . 119.5 ?
C8 C9 C10 . . 118.8(7) ?
C8 C9 H9 . . 120.6 ?
C10 C9 H9 . . 120.6 ?
C9 C10 C11 . . 120.7(7) ?
C9 C10 H10 . . 119.7 ?
C11 C10 H10 . . 119.7 ?
C10 C11 C12 . . 121.1(7) ?
C10 C11 H11 . . 119.5 ?
C12 C11 H11 . . 119.5 ?
C11 C12 C7 . . 116.5(5) ?
C11 C12 C13 . . 120.2(6) ?
C7 C12 C13 . . 123.3(5) ?
O1 C13 C12 . . 110.1(5) ?
O1 C13 C1 . . 105.9(5) ?
C12 C13 C1 . . 110.4(4) ?
O1 C13 C14 . . 106.5(5) ?
C12 C13 C14 . . 112.3(5) ?
C1 C13 C14 . . 111.4(5) ?
N1 C14 C15 . . 103.1(7) ?
N1 C14 C13 . . 108.9(5) ?
C15 C14 C13 . . 109.8(11) ?
N1 C14 C15' . . 110.1(12) ?
C15 C14 C15' . . 18(3) ?
C13 C14 C15' . . 121(2) ?
N1 C14 H14 . . 111.5 ?
C15 C14 H14 . . 111.5 ?
C13 C14 H14 . . 111.5 ?
C15' C14 H14 . . 93.2 ?
N1 C17 C16 . . 104.0(8) ?
N1 C17 H17A . . 110.9 ?
C16 C17 H17A . . 110.9 ?
N1 C17 H17B . . 110.9 ?
C16 C17 H17B . . 110.9 ?
H17A C17 H17B . . 109.0 ?
C15 C16 C17 . . 102.5(15) ?
C15 C16 H16A . . 111.3 ?
C17 C16 H16A . . 111.3 ?
C15 C16 H16B . . 111.3 ?
C17 C16 H16B . . 111.3 ?
H16A C16 H16B . . 109.2 ?
C16 C15 C14 . . 107.7(19) ?
C16 C15 H15A . . 110.2 ?
C14 C15 H15A . . 110.2 ?
C16 C15 H15B . . 110.2 ?
C14 C15 H15B . . 110.2 ?
H15A C15 H15B . . 108.5 ?
C16' C15' C14 . . 103(4) ?
C16' C15' H15C . . 111.2 ?
C14 C15' H15C . . 111.2 ?
C16' C15' H15D . . 111.2 ?
C14 C15' H15D . . 111.2 ?
H15C C15' H15D . . 109.1 ?
C17' C16' C15' . . 105(3) ?
C17' C16' H16C . . 110.7 ?
C15' C16' H16C . . 110.7 ?
C17' C16' H16D . . 110.7 ?
C15' C16' H16D . . 110.7 ?
H16C C16' H16D . . 108.8 ?
N1 C17' C16' . . 108.1(18) ?
N1 C17' H17C . . 110.1 ?
C16' C17' H17C . . 110.1 ?
N1 C17' H17D . . 110.1 ?
C16' C17' H17D . . 110.1 ?
H17C C17' H17D . . 108.4 ?
N1 C18 C19 . . 112.9(5) ?
N1 C18 H18A . . 109.0 ?
C19 C18 H18A . . 109.0 ?
N1 C18 H18B . . 109.0 ?
C19 C18 H18B . . 109.0 ?
H18A C18 H18B . . 107.8 ?
C24 C19 C20 . . 116.1(6) ?
C24 C19 C18 . . 121.6(6) ?
C20 C19 C18 . . 122.2(7) ?
C19 C20 C21 . . 120.6(7) ?
C19 C20 H20 . . 119.7 ?
C21 C20 H20 . . 119.7 ?
C22 C21 C20 . . 121.0(6) ?
C22 C21 H21 . . 119.5 ?
C20 C21 H21 . . 119.5 ?
C23 C22 C21 . . 119.1(6) ?
C23 C22 O2 . . 126.0(7) ?
C21 C22 O2 . . 115.0(7) ?
C22 C23 C24 . . 119.7(7) ?
C22 C23 H23 . . 120.1 ?
C24 C23 H23 . . 120.1 ?
C19 C24 C23 . . 123.4(6) ?
C19 C24 H24 . . 118.3 ?
C23 C24 H24 . . 118.3 ?
O2 C25 H25A . . 109.5 ?
O2 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
O2 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
C27 C26 C31 . . 117.0(6) ?
C27 C26 C38 . . 121.7(6) ?
C31 C26 C38 . . 121.3(6) ?
C26 C27 C28 . . 122.0(8) ?
C26 C27 H27 . . 119.0 ?
C28 C27 H27 . . 119.0 ?
C29 C28 C27 . . 121.2(9) ?
C29 C28 H28 . . 119.4 ?
C27 C28 H28 . . 119.4 ?
C28 C29 C30 . . 119.3(8) ?
C28 C29 H29 . . 120.4 ?
C30 C29 H29 . . 120.4 ?
C29 C30 C31 . . 119.8(9) ?
C29 C30 H30 . . 120.1 ?
C31 C30 H30 . . 120.1 ?
C26 C31 C30 . . 120.6(8) ?
C26 C31 H31 . . 119.7 ?
C30 C31 H31 . . 119.7 ?
C33 C32 C37 . . 117.7(6) ?
C33 C32 C38 . . 122.9(6) ?
C37 C32 C38 . . 119.4(6) ?
C34 C33 C32 . . 121.6(6) ?
C34 C33 H33 . . 119.2 ?
C32 C33 H33 . . 119.2 ?
C35 C34 C33 . . 120.5(7) ?
C35 C34 H34 . . 119.8 ?
C33 C34 H34 . . 119.8 ?
C36 C35 C34 . . 120.2(7) ?
C36 C35 H35 . . 119.9 ?
C34 C35 H35 . . 119.9 ?
C35 C36 C37 . . 120.5(7) ?
C35 C36 H36 . . 119.7 ?
C37 C36 H36 . . 119.7 ?
C36 C37 C32 . . 119.6(6) ?
C36 C37 H37 . . 120.2 ?
C32 C37 H37 . . 120.2 ?
O3 C38 C26 . . 106.5(5) ?
O3 C38 C32 . . 110.6(5) ?
C26 C38 C32 . . 108.3(5) ?
O3 C38 C39 . . 106.2(4) ?
C26 C38 C39 . . 112.4(5) ?
C32 C38 C39 . . 112.7(5) ?
N2 C39 C40 . . 104.0(4) ?
N2 C39 C38 . . 108.9(5) ?
C40 C39 C38 . . 114.2(5) ?
N2 C39 H39 . . 109.9 ?
C40 C39 H39 . . 109.9 ?
C38 C39 H39 . . 109.9 ?
C41 C40 C39 . . 106.5(5) ?
C41 C40 H40A . . 110.4 ?
C39 C40 H40A . . 110.4 ?
C41 C40 H40B . . 110.4 ?
C39 C40 H40B . . 110.4 ?
H40A C40 H40B . . 108.6 ?
C42 C41 C40 . . 104.8(6) ?
C42 C41 H41A . . 110.8 ?
C40 C41 H41A . . 110.8 ?
C42 C41 H41B . . 110.8 ?
C40 C41 H41B . . 110.8 ?
H41A C41 H41B . . 108.9 ?
C41 C42 N2 . . 106.4(6) ?
C41 C42 H42A . . 110.5 ?
N2 C42 H42A . . 110.5 ?
C41 C42 H42B . . 110.5 ?
N2 C42 H42B . . 110.5 ?
H42A C42 H42B . . 108.6 ?
N2 C43 C44 . . 113.1(5) ?
N2 C43 H43A . . 109.0 ?
C44 C43 H43A . . 109.0 ?
N2 C43 H43B . . 109.0 ?
C44 C43 H43B . . 109.0 ?
H43A C43 H43B . . 107.8 ?
C49 C44 C45 . . 115.9(6) ?
C49 C44 C43 . . 121.7(6) ?
C45 C44 C43 . . 122.4(7) ?
C44 C45 C46 . . 122.6(7) ?
C44 C45 H45 . . 118.7 ?
C46 C45 H45 . . 118.7 ?
C47 C46 C45 . . 118.9(6) ?
C47 C46 H46 . . 120.5 ?
C45 C46 H46 . . 120.5 ?
C46 C47 O4 . . 123.8(7) ?
C46 C47 C48 . . 120.3(6) ?
O4 C47 C48 . . 115.9(7) ?
C49 C48 C47 . . 117.9(7) ?
C49 C48 H48 . . 121.0 ?
C47 C48 H48 . . 121.0 ?
C44 C49 C48 . . 124.4(6) ?
C44 C49 H49 . . 117.8 ?
C48 C49 H49 . . 117.8 ?
O4 C50 H50A . . 109.5 ?
O4 C50 H50B . . 109.5 ?
H50A C50 H50B . . 109.5 ?
O4 C50 H50C . . 109.5 ?
H50A C50 H50C . . 109.5 ?
H50B C50 H50C . . 109.5 ?
C18 N1 C17 . . 119.8(8) ?
C18 N1 C14 . . 117.1(5) ?
C17 N1 C14 . . 112.0(7) ?
C18 N1 C17' . . 100.4(13) ?
C17 N1 C17' . . 34.3(9) ?
C14 N1 C17' . . 103.2(10) ?
C43 N2 C42 . . 113.0(5) ?
C43 N2 C39 . . 114.8(4) ?
C42 N2 C39 . . 106.2(5) ?
C13 O1 H1 . . 109.5 ?
C22 O2 C25 . . 116.9(6) ?
C38 O3 H3A . . 109.5 ?
C47 O4 C50 . . 116.6(8) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.362(10) ?
C1 C6 . 1.376(9) ?
C1 C13 . 1.540(8) ?
C2 C3 . 1.388(11) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.308(12) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.359(13) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.404(9) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.357(8) ?
C7 C12 . 1.389(8) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.360(10) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.369(11) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.379(9) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.383(8) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.525(8) ?
C13 O1 . 1.437(8) ?
C13 C14 . 1.548(9) ?
C14 N1 . 1.482(7) ?
C14 C15 . 1.55(4) ?
C14 C15' . 1.59(8) ?
C14 H14 . 0.9800 ?
C17 N1 . 1.481(8) ?
C17 C16 . 1.542(9) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C16 C15 . 1.531(10) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C15' C16' . 1.535(11) ?
C15' H15C . 0.9700 ?
C15' H15D . 0.9700 ?
C16' C17' . 1.528(10) ?
C16' H16C . 0.9700 ?
C16' H16D . 0.9700 ?
C17' N1 . 1.493(10) ?
C17' H17C . 0.9700 ?
C17' H17D . 0.9700 ?
C18 N1 . 1.444(7) ?
C18 C19 . 1.496(8) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C19 C24 . 1.371(9) ?
C19 C20 . 1.392(8) ?
C20 C21 . 1.392(8) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.372(9) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.353(9) ?
C22 O2 . 1.381(7) ?
C23 C24 . 1.381(8) ?
C23 H23 . 0.9300 ?
C24 H24 . 0.9300 ?
C25 O2 . 1.421(10) ?
C25 H25A . 0.9600 ?
C25 H25B . 0.9600 ?
C25 H25C . 0.9600 ?
C26 C27 . 1.350(9) ?
C26 C31 . 1.362(9) ?
C26 C38 . 1.529(8) ?
C27 C28 . 1.394(10) ?
C27 H27 . 0.9300 ?
C28 C29 . 1.291(13) ?
C28 H28 . 0.9300 ?
C29 C30 . 1.375(14) ?
C29 H29 . 0.9300 ?
C30 C31 . 1.403(10) ?
C30 H30 . 0.9300 ?
C31 H31 . 0.9300 ?
C32 C33 . 1.384(8) ?
C32 C37 . 1.411(8) ?
C32 C38 . 1.530(8) ?
C33 C34 . 1.366(8) ?
C33 H33 . 0.9300 ?
C34 C35 . 1.364(11) ?
C34 H34 . 0.9300 ?
C35 C36 . 1.363(10) ?
C35 H35 . 0.9300 ?
C36 C37 . 1.394(9) ?
C36 H36 . 0.9300 ?
C37 H37 . 0.9300 ?
C38 O3 . 1.438(7) ?
C38 C39 . 1.545(9) ?
C39 N2 . 1.493(7) ?
C39 C40 . 1.533(8) ?
C39 H39 . 0.9800 ?
C40 C41 . 1.499(8) ?
C40 H40A . 0.9700 ?
C40 H40B . 0.9700 ?
C41 C42 . 1.437(9) ?
C41 H41A . 0.9700 ?
C41 H41B . 0.9700 ?
C42 N2 . 1.461(8) ?
C42 H42A . 0.9700 ?
C42 H42B . 0.9700 ?
C43 N2 . 1.447(7) ?
C43 C44 . 1.507(8) ?
C43 H43A . 0.9700 ?
C43 H43B . 0.9700 ?
C44 C49 . 1.349(9) ?
C44 C45 . 1.375(8) ?
C45 C46 . 1.384(8) ?
C45 H45 . 0.9300 ?
C46 C47 . 1.362(10) ?
C46 H46 . 0.9300 ?
C47 O4 . 1.367(7) ?
C47 C48 . 1.378(9) ?
C48 C49 . 1.374(9) ?
C48 H48 . 0.9300 ?
C49 H49 . 0.9300 ?
C50 O4 . 1.415(12) ?
C50 H50A . 0.9600 ?
C50 H50B . 0.9600 ?
C50 H50C . 0.9600 ?
O1 H1 . 0.8200 ?
O3 H3A . 0.8200 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 N1 . 0.82 2.32 2.673(8) 106
O3 H3A N2 . 0.82 2.33 2.672(7) 106
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.3(11) ?
C13 C1 C2 C3 . . . . 179.1(7) ?
C1 C2 C3 C4 . . . . 2.2(15) ?
C2 C3 C4 C5 . . . . -2.9(16) ?
C3 C4 C5 C6 . . . . 1.9(15) ?
C2 C1 C6 C5 . . . . -0.6(11) ?
C13 C1 C6 C5 . . . . 180.0(7) ?
C4 C5 C6 C1 . . . . -0.2(14) ?
C12 C7 C8 C9 . . . . -1.2(10) ?
C7 C8 C9 C10 . . . . 0.7(10) ?
C8 C9 C10 C11 . . . . -0.2(11) ?
C9 C10 C11 C12 . . . . 0.3(11) ?
C10 C11 C12 C7 . . . . -0.8(9) ?
C10 C11 C12 C13 . . . . -180.0(6) ?
C8 C7 C12 C11 . . . . 1.2(8) ?
C8 C7 C12 C13 . . . . -179.6(5) ?
C11 C12 C13 O1 . . . . 8.0(7) ?
C7 C12 C13 O1 . . . . -171.2(5) ?
C11 C12 C13 C1 . . . . -108.6(6) ?
C7 C12 C13 C1 . . . . 72.3(7) ?
C11 C12 C13 C14 . . . . 126.5(6) ?
C7 C12 C13 C14 . . . . -52.6(7) ?
C2 C1 C13 O1 . . . . -0.2(8) ?
C6 C1 C13 O1 . . . . 179.2(6) ?
C2 C1 C13 C12 . . . . 118.9(7) ?
C6 C1 C13 C12 . . . . -61.7(8) ?
C2 C1 C13 C14 . . . . -115.7(7) ?
C6 C1 C13 C14 . . . . 63.7(8) ?
O1 C13 C14 N1 . . . . 46.6(6) ?
C12 C13 C14 N1 . . . . -74.1(6) ?
C1 C13 C14 N1 . . . . 161.6(5) ?
O1 C13 C14 C15 . . . . -65.7(10) ?
C12 C13 C14 C15 . . . . 173.7(9) ?
C1 C13 C14 C15 . . . . 49.4(10) ?
O1 C13 C14 C15' . . . . -82(2) ?
C12 C13 C14 C15' . . . . 157(2) ?
C1 C13 C14 C15' . . . . 33(2) ?
N1 C17 C16 C15 . . . . -31.8(18) ?
C17 C16 C15 C14 . . . . 29.8(18) ?
N1 C14 C15 C16 . . . . -16.0(18) ?
C13 C14 C15 C16 . . . . 99.9(16) ?
C15' C14 C15 C16 . . . . -130(7) ?
N1 C14 C15' C16' . . . . 4(5) ?
C15 C14 C15' C16' . . . . 75(5) ?
C13 C14 C15' C16' . . . . 132(3) ?
C14 C15' C16' C17' . . . . 16(5) ?
C15' C16' C17' N1 . . . . -31(4) ?
N1 C18 C19 C24 . . . . 69.7(8) ?
N1 C18 C19 C20 . . . . -108.7(7) ?
C24 C19 C20 C21 . . . . -0.3(9) ?
C18 C19 C20 C21 . . . . 178.2(6) ?
C19 C20 C21 C22 . . . . 2.6(10) ?
C20 C21 C22 C23 . . . . -2.4(10) ?
C20 C21 C22 O2 . . . . 177.7(6) ?
C21 C22 C23 C24 . . . . 0.0(10) ?
O2 C22 C23 C24 . . . . 179.8(6) ?
C20 C19 C24 C23 . . . . -2.2(10) ?
C18 C19 C24 C23 . . . . 179.3(6) ?
C22 C23 C24 C19 . . . . 2.4(10) ?
C31 C26 C27 C28 . . . . 0.8(11) ?
C38 C26 C27 C28 . . . . -177.2(7) ?
C26 C27 C28 C29 . . . . -3.8(14) ?
C27 C28 C29 C30 . . . . 5.6(15) ?
C28 C29 C30 C31 . . . . -4.6(15) ?
C27 C26 C31 C30 . . . . 0.2(11) ?
C38 C26 C31 C30 . . . . 178.1(7) ?
C29 C30 C31 C26 . . . . 1.7(13) ?
C37 C32 C33 C34 . . . . 1.0(8) ?
C38 C32 C33 C34 . . . . -177.9(6) ?
C32 C33 C34 C35 . . . . -1.4(9) ?
C33 C34 C35 C36 . . . . 1.2(10) ?
C34 C35 C36 C37 . . . . -0.8(10) ?
C35 C36 C37 C32 . . . . 0.4(9) ?
C33 C32 C37 C36 . . . . -0.5(8) ?
C38 C32 C37 C36 . . . . 178.4(5) ?
C27 C26 C38 O3 . . . . -18.6(8) ?
C31 C26 C38 O3 . . . . 163.5(6) ?
C27 C26 C38 C32 . . . . 100.4(7) ?
C31 C26 C38 C32 . . . . -77.5(7) ?
C27 C26 C38 C39 . . . . -134.5(7) ?
C31 C26 C38 C39 . . . . 47.7(8) ?
C33 C32 C38 O3 . . . . -172.7(5) ?
C37 C32 C38 O3 . . . . 8.5(7) ?
C33 C32 C38 C26 . . . . 70.9(7) ?
C37 C32 C38 C26 . . . . -107.9(6) ?
C33 C32 C38 C39 . . . . -54.1(7) ?
C37 C32 C38 C39 . . . . 127.1(5) ?
O3 C38 C39 N2 . . . . 46.9(6) ?
C26 C38 C39 N2 . . . . 162.9(5) ?
C32 C38 C39 N2 . . . . -74.3(5) ?
O3 C38 C39 C40 . . . . -68.8(6) ?
C26 C38 C39 C40 . . . . 47.2(6) ?
C32 C38 C39 C40 . . . . 170.0(5) ?
N2 C39 C40 C41 . . . . -0.7(8) ?
C38 C39 C40 C41 . . . . 117.9(7) ?
C39 C40 C41 C42 . . . . 21.2(10) ?
C40 C41 C42 N2 . . . . -34.2(10) ?
N2 C43 C44 C49 . . . . 81.8(7) ?
N2 C43 C44 C45 . . . . -100.0(7) ?
C49 C44 C45 C46 . . . . 1.7(10) ?
C43 C44 C45 C46 . . . . -176.6(6) ?
C44 C45 C46 C47 . . . . -1.5(11) ?
C45 C46 C47 O4 . . . . 179.4(6) ?
C45 C46 C47 C48 . . . . 0.9(11) ?
C46 C47 C48 C49 . . . . -0.6(11) ?
O4 C47 C48 C49 . . . . -179.2(6) ?
C45 C44 C49 C48 . . . . -1.3(10) ?
C43 C44 C49 C48 . . . . 177.0(6) ?
C47 C48 C49 C44 . . . . 0.8(11) ?
C19 C18 N1 C17 . . . . 51.2(15) ?
C19 C18 N1 C14 . . . . -167.6(6) ?
C19 C18 N1 C17' . . . . 81.6(13) ?
C16 C17 N1 C18 . . . . 166.6(10) ?
C16 C17 N1 C14 . . . . 23.6(17) ?
C16 C17 N1 C17' . . . . 105(3) ?
C15 C14 N1 C18 . . . . -149.1(12) ?
C13 C14 N1 C18 . . . . 94.3(7) ?
C15' C14 N1 C18 . . . . -131(3) ?
C15 C14 N1 C17 . . . . -5.0(17) ?
C13 C14 N1 C17 . . . . -121.6(14) ?
C15' C14 N1 C17 . . . . 13(3) ?
C15 C14 N1 C17' . . . . -39.9(18) ?
C13 C14 N1 C17' . . . . -156.5(15) ?
C15' C14 N1 C17' . . . . -22(3) ?
C16' C17' N1 C18 . . . . 154(2) ?
C16' C17' N1 C17 . . . . -77(3) ?
C16' C17' N1 C14 . . . . 32(2) ?
C44 C43 N2 C42 . . . . 72.0(7) ?
C44 C43 N2 C39 . . . . -166.0(6) ?
C41 C42 N2 C43 . . . . 161.0(7) ?
C41 C42 N2 C39 . . . . 34.4(8) ?
C40 C39 N2 C43 . . . . -145.4(6) ?
C38 C39 N2 C43 . . . . 92.5(6) ?
C40 C39 N2 C42 . . . . -19.8(7) ?
C38 C39 N2 C42 . . . . -141.9(6) ?
C23 C22 O2 C25 . . . . 1.6(9) ?
C21 C22 O2 C25 . . . . -178.6(6) ?
C46 C47 O4 C50 . . . . -13.6(11) ?
C48 C47 O4 C50 . . . . 165.0(8) ?
