#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:20:13 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180388 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/57/7205771.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_7205771
loop_
_publ_author_name
'Lemmerer, Andreas'
_publ_section_title
;
 Steric effects in hydrogen bonded columns of salts of benzoic acid and
 1-adamantanecarboxylic acid with the cyclic amines CnH2n+1NH2, n = 5,
 6, 7, 8 and 12
;
_journal_issue                   8
_journal_name_full               CrystEngComm
_journal_page_first              2849
_journal_paper_doi               10.1039/c0ce00749h
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C11 H15 O2, C12 H26 N'
_chemical_formula_sum            'C23 H41 N O2'
_chemical_formula_weight         363.57
_chemical_name_systematic
;
(cyclododecylammonium).(adamantanecarboxylate)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2010-10-13T10:19:18-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 102.386(1)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.9710(6)
_cell_length_b                   6.5850(1)
_cell_length_c                   23.0547(5)
_cell_measurement_reflns_used    5411
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.54
_cell_volume                     4295.87(15)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            13575
_diffrn_reflns_theta_full        28
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_min         1.44
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.07
_exptl_absorpt_correction_T_max  0.9816
_exptl_absorpt_correction_T_min  0.9603
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker XPREP (Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.124
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.644
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5186
_refine_ls_number_restraints     318
_refine_ls_restrained_S_all      0.628
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1553P)²+5.2249P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1569
_reflns_number_gt                3835
_reflns_number_total             5186
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00749h.txt
_cod_data_source_block           10
_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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7205771
loop_
_symmetry_equiv_pos_as_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'
'-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.62914(4) 0.21537(17) 0.63390(5) 0.0197(2) Uani 1 1 d . . .
C2A C 0.61686(5) 0.0633(2) 0.58253(6) 0.0284(3) Uani 0.928(2) 1 d PDU A 1
H2A1 H 0.6094 -0.0703 0.598 0.034 Uiso 0.928(2) 1 calc PR A 1
H2A2 H 0.6444 0.046 0.5639 0.034 Uiso 0.928(2) 1 calc PR A 1
C3A C 0.64016(5) 0.4223(2) 0.60885(6) 0.0244(3) Uani 0.928(2) 1 d PDU A 1
H3A1 H 0.6478 0.5226 0.6415 0.029 Uiso 0.928(2) 1 calc PR A 1
H3A2 H 0.668 0.4092 0.5906 0.029 Uiso 0.928(2) 1 calc PR A 1
C4A C 0.58581(5) 0.2406(2) 0.66214(6) 0.0263(3) Uani 0.928(2) 1 d PDU A 1
H4A1 H 0.5782 0.1089 0.6786 0.032 Uiso 0.928(2) 1 calc PR A 1
H4A2 H 0.5931 0.3397 0.6951 0.032 Uiso 0.928(2) 1 calc PR A 1
C5A C 0.57432(6) 0.1384(3) 0.53588(7) 0.0317(4) Uani 0.928(2) 1 d PDU A 1
H5A H 0.5668 0.0375 0.5028 0.038 Uiso 0.928(2) 1 calc PR A 1
C6A C 0.58605(6) 0.3425(3) 0.51141(7) 0.0327(4) Uani 0.928(2) 1 d PDU A 1
H6A1 H 0.5588 0.3907 0.4809 0.039 Uiso 0.928(2) 1 calc PR A 1
H6A2 H 0.6135 0.3275 0.4925 0.039 Uiso 0.928(2) 1 calc PR A 1
C7A C 0.59750(6) 0.4968(2) 0.56202(7) 0.0275(3) Uani 0.928(2) 1 d PDU A 1
H7A H 0.6051 0.631 0.546 0.033 Uiso 0.928(2) 1 calc PR A 1
C8A C 0.55507(6) 0.5200(3) 0.59101(8) 0.0319(4) Uani 0.928(2) 1 d PDU A 1
H8A1 H 0.5275 0.5705 0.5614 0.038 Uiso 0.928(2) 1 calc PR A 1
H8A2 H 0.5625 0.6202 0.6237 0.038 Uiso 0.928(2) 1 calc PR A 1
C9A C 0.54304(6) 0.3152(3) 0.61544(7) 0.0311(4) Uani 0.928(2) 1 d PDU A 1
H9A H 0.5151 0.3307 0.634 0.037 Uiso 0.928(2) 1 calc PR A 1
C10A C 0.53175(6) 0.1622(3) 0.56446(8) 0.0346(4) Uani 0.928(2) 1 d PDU A 1
H10A H 0.5237 0.0293 0.5798 0.041 Uiso 0.928(2) 1 calc PR A 1
H10B H 0.5041 0.2098 0.5344 0.041 Uiso 0.928(2) 1 calc PR A 1
C2B C 0.5871(5) 0.058(2) 0.6276(8) 0.032(3) Uani 0.072(2) 1 d PDU A 2
H2B1 H 0.5973 -0.0767 0.6163 0.038 Uiso 0.072(2) 1 calc PR A 2
H2B2 H 0.577 0.0452 0.6659 0.038 Uiso 0.072(2) 1 calc PR A 2
C3B C 0.6430(5) 0.232(3) 0.5742(7) 0.029(3) Uani 0.072(2) 1 d PDU A 2
H3B1 H 0.6546 0.0989 0.5636 0.035 Uiso 0.072(2) 1 calc PR A 2
H3B2 H 0.6692 0.3312 0.5774 0.035 Uiso 0.072(2) 1 calc PR A 2
C4B C 0.6117(5) 0.425(2) 0.6511(7) 0.024(3) Uani 0.072(2) 1 d PDU A 2
H4B1 H 0.6001 0.4131 0.6883 0.029 Uiso 0.072(2) 1 calc PR A 2
H4B2 H 0.6381 0.5237 0.6577 0.029 Uiso 0.072(2) 1 calc PR A 2
C5B C 0.5459(7) 0.137(3) 0.5794(9) 0.043(3) Uani 0.072(2) 1 d PDU A 2
H5B H 0.5186 0.0422 0.5753 0.052 Uiso 0.072(2) 1 calc PR A 2
C6B C 0.5624(8) 0.145(4) 0.5216(9) 0.046(3) Uani 0.072(2) 1 d PDU A 2
H6B1 H 0.5355 0.1799 0.4889 0.056 Uiso 0.072(2) 1 calc PR A 2
H6B2 H 0.5742 0.0093 0.5132 0.056 Uiso 0.072(2) 1 calc PR A 2
C7B C 0.6014(7) 0.301(3) 0.5244(9) 0.040(3) Uani 0.072(2) 1 d PDU A 2
H7B H 0.6114 0.3079 0.4856 0.048 Uiso 0.072(2) 1 calc PR A 2
C8B C 0.5871(9) 0.508(3) 0.5423(9) 0.041(3) Uani 0.072(2) 1 d PDU A 2
H8B1 H 0.6141 0.6023 0.5458 0.049 Uiso 0.072(2) 1 calc PR A 2
H8B2 H 0.5608 0.5603 0.5111 0.049 Uiso 0.072(2) 1 calc PR A 2
C9B C 0.5717(7) 0.499(3) 0.6005(8) 0.035(3) Uani 0.072(2) 1 d PDU A 2
H9B H 0.5609 0.6361 0.6103 0.042 Uiso 0.072(2) 1 calc PR A 2
C10B C 0.5313(6) 0.346(3) 0.5965(11) 0.041(3) Uani 0.072(2) 1 d PDU A 2
H10C H 0.522 0.3378 0.6353 0.049 Uiso 0.072(2) 1 calc PR A 2
H10D H 0.5035 0.3928 0.5666 0.049 Uiso 0.072(2) 1 calc PR A 2
C11 C 0.67102(4) 0.13883(18) 0.68123(5) 0.0215(2) Uani 1 1 d . A .
O1 O 0.68704(3) -0.03421(14) 0.67574(4) 0.0314(2) Uani 1 1 d . . .
O2 O 0.68786(3) 0.25602(13) 0.72441(4) 0.0270(2) Uani 1 1 d . . .
C12 C 0.70224(4) -0.33621(18) 0.81451(5) 0.0224(2) Uani 1 1 d . . .
H12 H 0.7191 -0.4494 0.8393 0.027 Uiso 1 1 calc R . .
C13 C 0.72046(4) -0.13629(19) 0.84439(5) 0.0243(3) Uani 1 1 d . . .
H13A H 0.7002 -0.024 0.8249 0.029 Uiso 1 1 calc R . .
H13B H 0.7529 -0.112 0.8386 0.029 Uiso 1 1 calc R . .
C14 C 0.72107(5) -0.1336(2) 0.91088(6) 0.0300(3) Uani 1 1 d . . .
H14A H 0.6911 -0.1922 0.9173 0.036 Uiso 1 1 calc R . .
H14B H 0.7472 -0.221 0.9318 0.036 Uiso 1 1 calc R . .
C15 C 0.72719(5) 0.0789(2) 0.93805(6) 0.0334(3) Uani 1 1 d . . .
H15A H 0.7557 0.142 0.9286 0.04 Uiso 1 1 calc R . .
H15B H 0.7325 0.0668 0.9818 0.04 Uiso 1 1 calc R . .
C16 C 0.68484(5) 0.2188(2) 0.91615(6) 0.0325(3) Uani 1 1 d . . .
H16A H 0.6774 0.219 0.8722 0.039 Uiso 1 1 calc R . .
H16B H 0.6937 0.359 0.9296 0.039 Uiso 1 1 calc R . .
C17 C 0.64048(6) 0.1573(3) 0.93802(7) 0.0387(3) Uani 1 1 d . . .
H17A H 0.6392 0.0072 0.9397 0.046 Uiso 1 1 calc R . .
H17B H 0.6434 0.2088 0.979 0.046 Uiso 1 1 calc R . .
C18 C 0.59409(6) 0.2345(2) 0.89992(7) 0.0399(4) Uani 1 1 d . . .
H18A H 0.5966 0.383 0.8947 0.048 Uiso 1 1 calc R . .
H18B H 0.5685 0.2103 0.9214 0.048 Uiso 1 1 calc R . .
C19 C 0.58041(5) 0.1354(2) 0.83863(7) 0.0380(3) Uani 1 1 d . . .
H19A H 0.553 0.2094 0.8149 0.046 Uiso 1 1 calc R . .
H19B H 0.6071 0.1506 0.8184 0.046 Uiso 1 1 calc R . .
C20 C 0.56772(5) -0.0898(2) 0.83961(8) 0.0398(4) Uani 1 1 d . . .
H20A H 0.5905 -0.1571 0.872 0.048 Uiso 1 1 calc R . .
H20B H 0.536 -0.1023 0.8487 0.048 Uiso 1 1 calc R . .
C21 C 0.56775(5) -0.2012(2) 0.78150(7) 0.0370(3) Uani 1 1 d . . .
H21A H 0.5467 -0.1281 0.7486 0.044 Uiso 1 1 calc R . .
H21B H 0.5545 -0.339 0.7837 0.044 Uiso 1 1 calc R . .
C22 C 0.61693(4) -0.2204(2) 0.76713(6) 0.0289(3) Uani 1 1 d . . .
H22A H 0.6134 -0.266 0.7255 0.035 Uiso 1 1 calc R . .
H22B H 0.6321 -0.085 0.7707 0.035 Uiso 1 1 calc R . .
C23 C 0.64915(4) -0.3698(2) 0.80805(6) 0.0268(3) Uani 1 1 d . . .
H23A H 0.6418 -0.362 0.848 0.032 Uiso 1 1 calc R . .
H23B H 0.6414 -0.509 0.7929 0.032 Uiso 1 1 calc R . .
N1 N 0.71452(3) -0.34748(15) 0.75467(4) 0.0217(2) Uani 1 1 d . . .
H1A H 0.7009 -0.2417 0.7319 0.033 Uiso 1 1 calc R . .
H1B H 0.7037 -0.4666 0.7368 0.033 Uiso 1 1 calc R . .
H1C H 0.7465 -0.341 0.759 0.033 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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.261
0 1 0 0.275
-1 0 0 0.113
1 0 0 0.152
0 0 1 0.313
1 0 -2 0.286
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
C3B C1 C11 110.3(5) . . ?
C3B C1 C2A 53.9(7) . . ?
C11 C1 C2A 110.63(10) . . ?
C3B C1 C3A 58.6(7) . . ?
C11 C1 C3A 111.21(9) . . ?
C2A C1 C3A 108.70(10) . . ?
C3B C1 C4A 140.6(5) . . ?
C11 C1 C4A 109.07(10) . . ?
C2A C1 C4A 108.74(10) . . ?
C3A C1 C4A 108.42(10) . . ?
C3B C1 C4B 109.3(9) . . ?
C11 C1 C4B 111.2(5) . . ?
C2A C1 C4B 138.1(5) . . ?
C3A C1 C4B 54.0(6) . . ?
C4A C1 C4B 57.1(6) . . ?
C3B C1 C2B 108.3(9) . . ?
C11 C1 C2B 109.1(6) . . ?
C2A C1 C2B 57.0(7) . . ?
C3A C1 C2B 139.6(6) . . ?
C4A C1 C2B 55.1(7) . . ?
C4B C1 C2B 108.6(9) . . ?
C1 C2A C5A 110.47(12) . . ?
C1 C2A H2A1 109.6 . . ?
C5A C2A H2A1 109.6 . . ?
C1 C2A H2A2 109.6 . . ?
C5A C2A H2A2 109.6 . . ?
H2A1 C2A H2A2 108.1 . . ?
C7A C3A C1 110.24(11) . . ?
C7A C3A H3A1 109.6 . . ?
C1 C3A H3A1 109.6 . . ?
C7A C3A H3A2 109.6 . . ?
C1 C3A H3A2 109.6 . . ?
H3A1 C3A H3A2 108.1 . . ?
C9A C4A C1 110.22(11) . . ?
C9A C4A H4A1 109.6 . . ?
C1 C4A H4A1 109.6 . . ?
C9A C4A H4A2 109.6 . . ?
C1 C4A H4A2 109.6 . . ?
H4A1 C4A H4A2 108.1 . . ?
C6A C5A C10A 109.53(16) . . ?
C6A C5A C2A 109.54(13) . . ?
C10A C5A C2A 109.43(14) . . ?
C6A C5A H5A 109.4 . . ?
C10A C5A H5A 109.4 . . ?
C2A C5A H5A 109.4 . . ?
C5A C6A C7A 109.44(14) . . ?
C5A C6A H6A1 109.8 . . ?
C7A C6A H6A1 109.8 . . ?
C5A C6A H6A2 109.8 . . ?
C7A C6A H6A2 109.8 . . ?
H6A1 C6A H6A2 108.2 . . ?
C8A C7A C6A 109.69(14) . . ?
C8A C7A C3A 109.02(13) . . ?
C6A C7A C3A 109.50(13) . . ?
C8A C7A H7A 109.5 . . ?
C6A C7A H7A 109.5 . . ?
C3A C7A H7A 109.5 . . ?
C7A C8A C9A 109.96(13) . . ?
C7A C8A H8A1 109.7 . . ?
C9A C8A H8A1 109.7 . . ?
C7A C8A H8A2 109.7 . . ?
C9A C8A H8A2 109.7 . . ?
H8A1 C8A H8A2 108.2 . . ?
C10A C9A C8A 109.02(14) . . ?
C10A C9A C4A 109.58(14) . . ?
C8A C9A C4A 109.05(13) . . ?
C10A C9A H9A 109.7 . . ?
C8A C9A H9A 109.7 . . ?
C4A C9A H9A 109.7 . . ?
C5A C10A C9A 109.88(13) . . ?
C5A C10A H10A 109.7 . . ?
C9A C10A H10A 109.7 . . ?
C5A C10A H10B 109.7 . . ?
C9A C10A H10B 109.7 . . ?
H10A C10A H10B 108.2 . . ?
C5B C2B C1 108.0(12) . . ?
C5B C2B H2B1 110.1 . . ?
C1 C2B H2B1 110.1 . . ?
C5B C2B H2B2 110.1 . . ?
C1 C2B H2B2 110.1 . . ?
H2B1 C2B H2B2 108.4 . . ?
C1 C3B C7B 112.3(12) . . ?
C1 C3B H3B1 109.1 . . ?
C7B C3B H3B1 109.1 . . ?
C1 C3B H3B2 109.1 . . ?
C7B C3B H3B2 109.2 . . ?
H3B1 C3B H3B2 107.9 . . ?
C9B C4B C1 108.7(12) . . ?
C9B C4B H4B1 109.9 . . ?
C1 C4B H4B1 109.9 . . ?
C9B C4B H4B2 109.9 . . ?
C1 C4B H4B2 110 . . ?
H4B1 C4B H4B2 108.3 . . ?
C6B C5B C10B 111.1(17) . . ?
C6B C5B C2B 107.8(16) . . ?
C10B C5B C2B 109.6(15) . . ?
C6B C5B H5B 109.4 . . ?
C10B C5B H5B 109.4 . . ?
C2B C5B H5B 109.4 . . ?
C5B C6B C7B 111.0(16) . . ?
C5B C6B H6B1 109.4 . . ?
C7B C6B H6B1 109.4 . . ?
C5B C6B H6B2 109.4 . . ?
C7B C6B H6B2 109.4 . . ?
H6B1 C6B H6B2 108 . . ?
C8B C7B C6B 112.2(17) . . ?
C8B C7B C3B 106.1(15) . . ?
C6B C7B C3B 106.9(15) . . ?
C8B C7B H7B 110.5 . . ?
C6B C7B H7B 110.5 . . ?
C3B C7B H7B 110.5 . . ?
C9B C8B C7B 111.1(16) . . ?
C9B C8B H8B1 109.4 . . ?
C7B C8B H8B1 109.4 . . ?
C9B C8B H8B2 109.4 . . ?
C7B C8B H8B2 109.4 . . ?
H8B1 C8B H8B2 108 . . ?
C8B C9B C10B 110.0(16) . . ?
C8B C9B C4B 111.8(15) . . ?
C10B C9B C4B 106.3(14) . . ?
C8B C9B H9B 109.6 . . ?
C10B C9B H9B 109.6 . . ?
C4B C9B H9B 109.6 . . ?
C5B C10B C9B 111.0(15) . . ?
C5B C10B H10C 109.4 . . ?
C9B C10B H10C 109.4 . . ?
C5B C10B H10D 109.4 . . ?
C9B C10B H10D 109.4 . . ?
H10C C10B H10D 108 . . ?
O1 C11 O2 123.07(11) . . ?
O1 C11 C1 118.89(11) . . ?
O2 C11 C1 118.03(10) . . ?
N1 C12 C13 109.31(10) . . ?
N1 C12 C23 109.61(10) . . ?
C13 C12 C23 114.32(10) . . ?
N1 C12 H12 107.8 . . ?
C13 C12 H12 107.8 . . ?
C23 C12 H12 107.8 . . ?
C12 C13 C14 113.00(11) . . ?
C12 C13 H13A 109 . . ?
C14 C13 H13A 109 . . ?
C12 C13 H13B 109 . . ?
C14 C13 H13B 109 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C13 113.38(11) . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 C16 113.67(11) . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 C17 113.70(12) . . ?
C15 C16 H16A 108.8 . . ?
C17 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
C17 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C16 114.81(12) . . ?
C18 C17 H17A 108.6 . . ?
C16 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
C16 C17 H17B 108.6 . . ?
H17A C17 H17B 107.5 . . ?
C17 C18 C19 114.28(12) . . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C19 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C20 C19 C18 114.56(13) . . ?
C20 C19 H19A 108.6 . . ?
C18 C19 H19A 108.6 . . ?
C20 C19 H19B 108.6 . . ?
C18 C19 H19B 108.6 . . ?
H19A C19 H19B 107.6 . . ?
C21 C20 C19 114.04(13) . . ?
C21 C20 H20A 108.7 . . ?
C19 C20 H20A 108.7 . . ?
C21 C20 H20B 108.7 . . ?
C19 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
C20 C21 C22 113.81(12) . . ?
C20 C21 H21A 108.8 . . ?
C22 C21 H21A 108.8 . . ?
C20 C21 H21B 108.8 . . ?
C22 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C23 C22 C21 112.98(11) . . ?
C23 C22 H22A 109 . . ?
C21 C22 H22A 109 . . ?
C23 C22 H22B 109 . . ?
C21 C22 H22B 109 . . ?
H22A C22 H22B 107.8 . . ?
C12 C23 C22 115.72(11) . . ?
C12 C23 H23A 108.4 . . ?
C22 C23 H23A 108.4 . . ?
C12 C23 H23B 108.4 . . ?
C22 C23 H23B 108.4 . . ?
H23A C23 H23B 107.4 . . ?
C12 N1 H1A 109.5 . . ?
C12 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C12 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 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
C1 C3B 1.519(16) . ?
C1 C11 1.5327(16) . ?
C1 C2A 1.5332(17) . ?
C1 C3A 1.5396(17) . ?
C1 C4A 1.5422(17) . ?
C1 C4B 1.550(15) . ?
C1 C2B 1.580(15) . ?
C2A C5A 1.533(2) . ?
C2A H2A1 0.99 . ?
C2A H2A2 0.99 . ?
C3A C7A 1.5370(19) . ?
C3A H3A1 0.99 . ?
C3A H3A2 0.99 . ?
C4A C9A 1.537(2) . ?
C4A H4A1 0.99 . ?
C4A H4A2 0.99 . ?
C5A C6A 1.524(2) . ?
C5A C10A 1.526(2) . ?
C5A H5A 1 . ?
C6A C7A 1.529(2) . ?
C6A H6A1 0.99 . ?
C6A H6A2 0.99 . ?
C7A C8A 1.528(2) . ?
C7A H7A 1 . ?
C8A C9A 1.530(2) . ?
C8A H8A1 0.99 . ?
C8A H8A2 0.99 . ?
C9A C10A 1.529(2) . ?
C9A H9A 1 . ?
C10A H10A 0.99 . ?
C10A H10B 0.99 . ?
C2B C5B 1.536(16) . ?
C2B H2B1 0.99 . ?
C2B H2B2 0.99 . ?
C3B C7B 1.542(16) . ?
C3B H3B1 0.99 . ?
C3B H3B2 0.99 . ?
C4B C9B 1.537(16) . ?
C4B H4B1 0.99 . ?
C4B H4B2 0.99 . ?
C5B C6B 1.508(18) . ?
C5B C10B 1.513(17) . ?
C5B H5B 1 . ?
C6B C7B 1.517(18) . ?
C6B H6B1 0.99 . ?
C6B H6B2 0.99 . ?
C7B C8B 1.508(17) . ?
C7B H7B 1 . ?
C8B C9B 1.503(17) . ?
C8B H8B1 0.99 . ?
C8B H8B2 0.99 . ?
C9B C10B 1.532(17) . ?
C9B H9B 1 . ?
C10B H10C 0.99 . ?
C10B H10D 0.99 . ?
C11 O1 1.2470(15) . ?
C11 O2 1.2711(15) . ?
C12 N1 1.4985(15) . ?
C12 C13 1.5266(17) . ?
C12 C23 1.5294(17) . ?
C12 H12 1 . ?
C13 C14 1.5293(18) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 C15 1.5279(19) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C15 C16 1.531(2) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C16 C17 1.532(2) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C17 C18 1.526(2) . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C18 C19 1.530(2) . ?
C18 H18A 0.99 . ?
C18 H18B 0.99 . ?
C19 C20 1.529(2) . ?
C19 H19A 0.99 . ?
C19 H19B 0.99 . ?
C20 C21 1.528(2) . ?
C20 H20A 0.99 . ?
C20 H20B 0.99 . ?
C21 C22 1.5358(18) . ?
C21 H21A 0.99 . ?
C21 H21B 0.99 . ?
C22 C23 1.5335(18) . ?
C22 H22A 0.99 . ?
C22 H22B 0.99 . ?
C23 H23A 0.99 . ?
C23 H23B 0.99 . ?
N1 H1A 0.91 . ?
N1 H1B 0.91 . ?
N1 H1C 0.91 . ?
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 H1A O1 0.91 1.87 2.753(1) 164 .
N1 H1B O2 0.91 1.89 2.769(1) 162 1_545
N1 H1C O2 0.91 1.97 2.848(1) 163 4_646
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
C3B C1 C2A C5A -80.5(7) . . . . ?
C11 C1 C2A C5A 178.86(11) . . . . ?
C3A C1 C2A C5A -58.76(15) . . . . ?
C4A C1 C2A C5A 59.09(15) . . . . ?
C4B C1 C2A C5A -2.2(9) . . . . ?
C2B C1 C2A C5A 78.9(7) . . . . ?
C3B C1 C3A C7A 79.2(7) . . . . ?
C11 C1 C3A C7A -179.39(11) . . . . ?
C2A C1 C3A C7A 58.58(14) . . . . ?
C4A C1 C3A C7A -59.48(14) . . . . ?
C4B C1 C3A C7A -78.0(7) . . . . ?
C2B C1 C3A C7A -2.1(12) . . . . ?
C3B C1 C4A C9A -3.2(11) . . . . ?
C11 C1 C4A C9A -179.40(11) . . . . ?
C2A C1 C4A C9A -58.67(14) . . . . ?
C3A C1 C4A C9A 59.35(14) . . . . ?
C4B C1 C4A C9A 77.2(6) . . . . ?
C2B C1 C4A C9A -79.0(7) . . . . ?
C1 C2A C5A C6A 60.10(17) . . . . ?
C1 C2A C5A C10A -59.99(17) . . . . ?
C10A C5A C6A C7A 59.89(18) . . . . ?
C2A C5A C6A C7A -60.14(18) . . . . ?
C5A C6A C7A C8A -59.52(18) . . . . ?
C5A C6A C7A C3A 60.09(17) . . . . ?
C1 C3A C7A C8A 60.29(15) . . . . ?
C1 C3A C7A C6A -59.73(16) . . . . ?
C6A C7A C8A C9A 59.50(18) . . . . ?
C3A C7A C8A C9A -60.39(17) . . . . ?
C7A C8A C9A C10A -59.30(18) . . . . ?
C7A C8A C9A C4A 60.30(17) . . . . ?
C1 C4A C9A C10A 59.26(16) . . . . ?
C1 C4A C9A C8A -60.00(16) . . . . ?
C6A C5A C10A C9A -60.37(19) . . . . ?
C2A C5A C10A C9A 59.73(18) . . . . ?
C8A C9A C10A C5A 59.72(19) . . . . ?
C4A C9A C10A C5A -59.55(18) . . . . ?
C3B C1 C2B C5B -59.2(15) . . . . ?
C11 C1 C2B C5B -179.2(11) . . . . ?
C2A C1 C2B C5B -76.5(13) . . . . ?
C3A C1 C2B C5B 3(2) . . . . ?
C4A C1 C2B C5B 80.4(13) . . . . ?
C4B C1 C2B C5B 59.4(15) . . . . ?
C11 C1 C3B C7B 177.7(11) . . . . ?
C2A C1 C3B C7B 76.4(12) . . . . ?
C3A C1 C3B C7B -79.3(12) . . . . ?
C4A C1 C3B C7B 2(2) . . . . ?
C4B C1 C3B C7B -59.8(15) . . . . ?
C2B C1 C3B C7B 58.4(15) . . . . ?
C3B C1 C4B C9B 54.9(14) . . . . ?
C11 C1 C4B C9B 176.9(10) . . . . ?
C2A C1 C4B C9B -2.1(17) . . . . ?
C3A C1 C4B C9B 75.5(11) . . . . ?
C4A C1 C4B C9B -83.5(11) . . . . ?
C2B C1 C4B C9B -63.0(14) . . . . ?
C1 C2B C5B C6B 62.5(18) . . . . ?
C1 C2B C5B C10B -58.6(19) . . . . ?
C10B C5B C6B C7B 55(2) . . . . ?
C2B C5B C6B C7B -66(2) . . . . ?
C5B C6B C7B C8B -54(2) . . . . ?
C5B C6B C7B C3B 62(2) . . . . ?
C1 C3B C7B C8B 61.2(18) . . . . ?
C1 C3B C7B C6B -58.6(18) . . . . ?
C6B C7B C8B C9B 56(2) . . . . ?
C3B C7B C8B C9B -61(2) . . . . ?
C7B C8B C9B C10B -57(2) . . . . ?
C7B C8B C9B C4B 61(2) . . . . ?
C1 C4B C9B C8B -56.4(18) . . . . ?
C1 C4B C9B C10B 63.6(17) . . . . ?
C6B C5B C10B C9B -57(2) . . . . ?
C2B C5B C10B C9B 63(2) . . . . ?
C8B C9B C10B C5B 57(2) . . . . ?
C4B C9B C10B C5B -64(2) . . . . ?
C3B C1 C11 O1 -63.3(7) . . . . ?
C2A C1 C11 O1 -5.47(16) . . . . ?
C3A C1 C11 O1 -126.37(12) . . . . ?
C4A C1 C11 O1 114.10(12) . . . . ?
C4B C1 C11 O1 175.3(7) . . . . ?
C2B C1 C11 O1 55.5(8) . . . . ?
C3B C1 C11 O2 116.6(7) . . . . ?
C2A C1 C11 O2 174.43(11) . . . . ?
C3A C1 C11 O2 53.53(14) . . . . ?
C4A C1 C11 O2 -66.00(13) . . . . ?
C4B C1 C11 O2 -4.8(7) . . . . ?
C2B C1 C11 O2 -124.6(8) . . . . ?
N1 C12 C13 C14 -165.26(10) . . . . ?
C23 C12 C13 C14 71.47(14) . . . . ?
C12 C13 C14 C15 -165.58(11) . . . . ?
C13 C14 C15 C16 67.69(16) . . . . ?
C14 C15 C16 C17 69.02(16) . . . . ?
C15 C16 C17 C18 -157.19(13) . . . . ?
C16 C17 C18 C19 69.17(18) . . . . ?
C17 C18 C19 C20 67.46(17) . . . . ?
C18 C19 C20 C21 -163.65(12) . . . . ?
C19 C20 C21 C22 67.10(17) . . . . ?
C20 C21 C22 C23 70.99(16) . . . . ?
N1 C12 C23 C22 -58.22(14) . . . . ?
C13 C12 C23 C22 64.89(15) . . . . ?
C21 C22 C23 C12 -156.05(12) . . . . ?
