#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/86/2008686.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_2008686
loop_
_publ_author_name
'Pai Fondekar, Kamalesh'
'Volk, Franz-Josef'
'Weckert, Edgar'
'Frahm, August W.'
_publ_section_title
;
 (1S,2R)-1-Amino-2-methoxycyclohexane-1-carboxamide
 hydrochloride 0.25-hydrate
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1167
_journal_page_last               1170
_journal_paper_doi               10.1107/S0108270199003522
_journal_volume                  55
_journal_year                    1999
_chemical_formula_iupac          'C8 H17 N2 O2 + , Cl - , 0.25(H2 O)'
_chemical_formula_sum            'C8 H17.5 Cl N2 O2.25'
_chemical_formula_weight         213.19
_chemical_melting_point          480
_chemical_name_systematic
;
(1S,2R)-1-Amino-2-methoxycyclohexane-1-carboxamide hydrochloride 0.25 hydrate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   11.507(2)
_cell_length_b                   15.225(5)
_cell_length_c                   24.573(9)
_cell_measurement_reflns_used    31034
_cell_measurement_temperature    110.0(10)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      3
_cell_volume                     4305(2)
_computing_cell_refinement       XDS98
_computing_data_collection       'XDS98 (Kabsch, 1993)'
_computing_data_reduction        XDS98
_computing_molecular_graphics    'CRYSTAN88 (Burzlaff & Rothammel, 1988)'
_computing_publication_material  'SHELXL97 and local software'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      110.0(10)
_diffrn_detector_area_resol_mean 6.667
_diffrn_measured_fraction_theta_full 0.9472
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'MAR 180mm image plate'
_diffrn_measurement_method       'area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_av_sigmaI/netI    0.020
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            32715
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         25.95
_diffrn_reflns_theta_min         2.37
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1848
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.161
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     575
_refine_ls_number_reflns         8023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.025
_refine_ls_R_factor_gt           0.024
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0352P)²+1.0952P], P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.063
_reflns_number_gt                7962
_reflns_number_total             8023
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jz1343.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 'Orthorhombic' changed to
'orthorhombic' 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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0352P)^2^+1.0952P], P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0352P)^2^+1.0952P], P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_formula_sum        'C8 H17 Cl N2 O2 , 0.25(H2 O)'
_cod_database_code               2008686
_cod_database_fobs_code          2008686
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_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
_atom_site_type_symbol
Cl1 0.62431(3) 0.01109(2) 0.859646(13) 0.01555(7) Uani d . 1 . . Cl
N1 0.63943(11) 0.18262(8) 0.78319(5) 0.0129(2) Uani d . 1 . . N
H1A 0.6125(18) 0.2127(14) 0.8095(8) 0.024(3) Uiso d . 1 . . H
H1B 0.713(2) 0.1931(13) 0.7804(8) 0.024(3) Uiso d . 1 . . H
H1C 0.6331(17) 0.1265(14) 0.7950(8) 0.024(3) Uiso d . 1 . . H
N2 0.50454(13) 0.33368(9) 0.68629(5) 0.0202(3) Uani d . 1 . . N
H2A 0.4622(19) 0.3006(14) 0.6673(8) 0.030(4) Uiso d . 1 . . H
H2B 0.494(2) 0.3811(16) 0.6847(8) 0.030(4) Uiso d . 1 . . H
O1 0.40097(9) 0.17656(7) 0.78557(4) 0.0211(2) Uani d . 1 . . O
O2 0.62496(9) 0.34763(7) 0.75824(4) 0.0191(2) Uani d . 1 . . O
C1 0.57522(13) 0.20093(9) 0.73121(5) 0.0129(3) Uani d . 1 . . C
C2 0.45526(13) 0.15582(9) 0.73518(6) 0.0149(3) Uani d . 1 . . C
H21 0.4081(15) 0.1759(11) 0.7025(6) 0.010(4) Uiso d . 1 . . H
C3 0.46576(14) 0.05604(9) 0.73283(6) 0.0178(3) Uani d . 1 . . C
H31 0.3870 0.0298 0.7326 0.021 Uiso calc R 1 . . H
H32 0.5064 0.0350 0.7659 0.021 Uiso calc R 1 . . H
C4 0.53211(16) 0.02538(10) 0.68246(6) 0.0235(3) Uani d . 1 . . C
H41 0.5384 -0.0395 0.6829 0.028 Uiso calc R 1 . . H
H42 0.4888 0.0427 0.6493 0.028 Uiso calc R 1 . . H
C5 0.65293(15) 0.06537(10) 0.68093(6) 0.0238(3) Uani d . 1 . . C
H51 0.6936 0.0463 0.6474 0.029 Uiso calc R 1 . . H
H52 0.6983 0.0447 0.7127 0.029 Uiso calc R 1 . . H
C6 0.64469(13) 0.16591(10) 0.68202(6) 0.0181(3) Uani d . 1 . . C
H61 0.6071 0.1863 0.6481 0.022 Uiso calc R 1 . . H
H62 0.7241 0.1908 0.6831 0.022 Uiso calc R 1 . . H
C7 0.56895(13) 0.30190(9) 0.72641(5) 0.0143(3) Uani d . 1 . . C
C8 0.34208(15) 0.25838(11) 0.78810(7) 0.0280(3) Uani d G 1 . . C
H8C 0.3979 0.3051 0.7965 0.034 Uiso calc R 1 . . H
H8D 0.2825 0.2561 0.8166 0.034 Uiso calc R 1 . . H
H8E 0.3052 0.2705 0.7529 0.034 Uiso calc R 1 . . H
Cl2 -0.08718(3) 0.21166(2) 0.785153(15) 0.01865(8) Uani d . 1 . . Cl
N11 0.15441(11) -0.08896(8) 0.72117(5) 0.0145(2) Uani d . 1 . . N
H11A 0.1556(17) -0.0921(13) 0.6848(8) 0.024(3) Uiso d . 1 . . H
H11B 0.1171(18) -0.1375(14) 0.7339(8) 0.024(3) Uiso d . 1 . . H
H11C 0.2305(19) -0.0895(13) 0.7348(8) 0.024(3) Uiso d . 1 . . H
N12 0.13557(12) 0.14886(8) 0.71736(5) 0.0167(2) Uani d . 1 . . N
H12A 0.1624(17) 0.1870(13) 0.6957(8) 0.021(3) Uiso d . 1 . . H
H12B 0.0850(18) 0.1636(13) 0.7407(8) 0.021(3) Uiso d . 1 . . H
O11 0.22730(10) 0.00212(7) 0.80992(4) 0.0210(2) Uani d . 1 . . O
O12 0.21937(9) 0.04391(7) 0.66579(4) 0.0170(2) Uani d . 1 . . O
C11 0.09413(12) -0.00601(9) 0.73737(5) 0.0140(3) Uani d . 1 . . C
C12 0.10632(13) 0.00550(10) 0.79904(5) 0.0166(3) Uani d . 1 . . C
H121 0.0807(17) 0.0620(13) 0.8076(7) 0.020(4) Uiso d . 1 . . H
C13 0.03953(15) -0.06589(11) 0.82979(6) 0.0241(3) Uani d . 1 . . C
H131 0.0758 -0.1237 0.8225 0.029 Uiso calc R 1 . . H
H132 0.0448 -0.0545 0.8694 0.029 Uiso calc R 1 . . H
C14 -0.08794(16) -0.06880(11) 0.81296(7) 0.0288(4) Uani d . 1 . . C
H141 -0.1264 -0.0135 0.8241 0.035 Uiso calc R 1 . . H
H142 -0.1270 -0.1178 0.8321 0.035 Uiso calc R 1 . . H
C15 -0.10150(14) -0.08098(10) 0.75161(7) 0.0231(3) Uani d . 1 . . C
H151 -0.1848 -0.0777 0.7418 0.028 Uiso calc R 1 . . H
H152 -0.0724 -0.1398 0.7411 0.028 Uiso calc R 1 . . H
C16 -0.03419(13) -0.01036(9) 0.72039(6) 0.0175(3) Uani d . 1 . . C
H161 -0.0709 0.0475 0.7269 0.021 Uiso calc R 1 . . H
H162 -0.0390 -0.0229 0.6809 0.021 Uiso calc R 1 . . H
C17 0.15640(12) 0.06593(9) 0.70396(5) 0.0132(3) Uani d . 1 . . C
C18 0.26025(16) 0.04507(11) 0.85912(6) 0.0263(3) Uani d . 1 . . C
H181 0.3446 0.0404 0.8640 0.032 Uiso calc R 1 . . H
H182 0.2207 0.0172 0.8899 0.032 Uiso calc R 1 . . H
H183 0.2381 0.1072 0.8572 0.032 Uiso calc R 1 . . H
Cl3 0.02783(3) 0.40377(2) 0.474355(16) 0.02334(9) Uani d . 1 . . Cl
N21 0.26028(11) 0.11316(8) 0.56236(5) 0.0128(2) Uani d . 1 . . N
H21A 0.2291(17) 0.0651(13) 0.5441(8) 0.023(3) Uiso d . 1 . . H
H21B 0.2479(16) 0.1051(13) 0.5974(8) 0.023(3) Uiso d . 1 . . H
H21C 0.336(2) 0.1105(12) 0.5566(7) 0.023(3) Uiso d . 1 . . H
N22 0.23665(12) 0.35260(8) 0.56878(5) 0.0169(2) Uani d . 1 . . N
H22A 0.2647(16) 0.3934(13) 0.5885(7) 0.018(3) Uiso d . 1 . . H
H22B 0.1918(17) 0.3692(12) 0.5430(8) 0.018(3) Uiso d . 1 . . H
O21 0.05387(9) 0.17843(7) 0.60514(4) 0.0170(2) Uani d . 1 . . O
O22 0.31916(10) 0.24711(7) 0.62084(4) 0.0214(2) Uani d . 1 . . O
C21 0.20826(13) 0.19849(8) 0.54331(5) 0.0123(3) Uani d . 1 . . C
C22 0.07584(13) 0.19460(9) 0.54897(5) 0.0132(3) Uani d . 1 . . C
H221 0.0464(15) 0.2489(12) 0.5381(7) 0.013(4) Uiso d . 1 . . H
C23 0.02160(13) 0.12599(9) 0.51112(6) 0.0175(3) Uani d . 1 . . C
H231 -0.0641 0.1282 0.5142 0.021 Uiso calc R 1 . . H
H232 0.0475 0.0666 0.5221 0.021 Uiso calc R 1 . . H
C24 0.05744(14) 0.14350(10) 0.45198(6) 0.0210(3) Uani d . 1 . . C
H241 0.0249 0.0969 0.4283 0.025 Uiso calc R 1 . . H
H242 0.0246 0.2004 0.4400 0.025 Uiso calc R 1 . . H
C25 0.18882(14) 0.14566(10) 0.44557(6) 0.0187(3) Uani d . 1 . . C
H251 0.2087 0.1602 0.4074 0.022 Uiso calc R 1 . . H
H252 0.2211 0.0869 0.4538 0.022 Uiso calc R 1 . . H
C26 0.24338(13) 0.21385(9) 0.48371(5) 0.0149(3) Uani d . 1 . . C
H261 0.2184 0.2734 0.4724 0.018 Uiso calc R 1 . . H
H262 0.3291 0.2110 0.4805 0.018 Uiso calc R 1 . . H
C27 0.25992(12) 0.26945(9) 0.58149(5) 0.0138(3) Uani d . 1 . . C
C28 -0.06387(14) 0.18977(11) 0.62060(6) 0.0233(3) Uani d . 1 . . C
H281 -0.0722 0.1779 0.6596 0.028 Uiso calc R 1 . . H
H282 -0.1128 0.1490 0.5999 0.028 Uiso calc R 1 . . H
H283 -0.0880 0.2503 0.6129 0.028 Uiso calc R 1 . . H
Cl4 0.28813(3) 0.08325(2) 1.011852(14) 0.01922(8) Uani d . 1 . . Cl
N31 0.53030(12) 0.40194(8) 0.94452(5) 0.0149(2) Uani d . 1 . . N
H31A 0.5391(18) 0.4003(14) 0.9077(9) 0.030(3) Uiso d . 1 . . H
H31B 0.607(2) 0.4038(14) 0.9578(8) 0.030(3) Uiso d . 1 . . H
H31C 0.4936(19) 0.4483(15) 0.9558(8) 0.030(3) Uiso d . 1 . . H
N32 0.48306(13) 0.16679(9) 0.92559(6) 0.0209(3) Uani d . 1 . . N
H32A 0.4393(19) 0.1532(13) 0.9528(9) 0.028(4) Uiso d . 1 . . H
H32B 0.5104(19) 0.1320(14) 0.9036(8) 0.028(4) Uiso d . 1 . . H
O31 0.31628(10) 0.36325(7) 0.90832(4) 0.0222(2) Uani d . 1 . . O
O32 0.57555(10) 0.27545(7) 0.87994(4) 0.0202(2) Uani d . 1 . . O
C31 0.47392(13) 0.31712(9) 0.96148(5) 0.0141(3) Uani d . 1 . . C
C32 0.34187(13) 0.32888(10) 0.96095(6) 0.0175(3) Uani d . 1 . . C
H321 0.3057(16) 0.2731(12) 0.9658(7) 0.018(4) Uiso d . 1 . . H
C33 0.29787(15) 0.38862(10) 1.00687(6) 0.0223(3) Uani d . 1 . . C
H331 0.3235 0.4497 0.9999 0.027 Uiso calc R 1 . . H
H332 0.2118 0.3880 1.0073 0.027 Uiso calc R 1 . . H
C34 0.34350(16) 0.35874(11) 1.06232(6) 0.0258(3) Uani d . 1 . . C
H341 0.3169 0.4002 1.0907 0.031 Uiso calc R 1 . . H
H342 0.3115 0.3000 1.0710 0.031 Uiso calc R 1 . . H
C35 0.47575(15) 0.35454(11) 1.06252(6) 0.0233(3) Uani d . 1 . . C
H351 0.5033 0.3342 1.0985 0.028 Uiso calc R 1 . . H
H352 0.5081 0.4139 1.0559 0.028 Uiso calc R 1 . . H
C36 0.51808(13) 0.29144(10) 1.01825(5) 0.0172(3) Uani d . 1 . . C
H361 0.4911 0.2313 1.0269 0.021 Uiso calc R 1 . . H
H362 0.6041 0.2909 1.0180 0.021 Uiso calc R 1 . . H
C37 0.51441(13) 0.24969(9) 0.91818(5) 0.0158(3) Uani d . 1 . . C
C38 0.19507(16) 0.36725(13) 0.89631(7) 0.0313(4) Uani d . 1 . . C
H381 0.1840 0.3913 0.8597 0.038 Uiso calc R 1 . . H
H382 0.1562 0.4051 0.9229 0.038 Uiso calc R 1 . . H
H383 0.1618 0.3081 0.8981 0.038 Uiso calc R 1 . . H
O41 -0.08432(12) 0.36161(9) 0.88115(5) 0.0295(3) Uani d . 1 . . O
H411 -0.095(3) 0.307(2) 0.8738(11) 0.065(8) Uiso d . 1 . . H
H412 -0.116(3) 0.366(2) 0.9139(14) 0.086(11) Uiso d . 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl- 0.1320 0.1590 '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
C1 N1 H1A 111.5(13) n
C1 N1 H1B 112.4(13) n
H1A N1 H1B 108.5(19) n
C1 N1 H1C 114.2(12) n
H1A N1 H1C 103.6(18) n
H1B N1 H1C 106.2(18) n
C7 N2 H2A 121.2(14) n
C7 N2 H2B 119.5(17) n
H2A N2 H2B 118(2) n
C8 O1 C2 116.27(12) y
N1 C1 C7 105.84(10) y
N1 C1 C6 110.31(12) y
C7 C1 C6 107.95(11) y
N1 C1 C2 107.66(11) y
C7 C1 C2 113.94(12) y
C6 C1 C2 111.01(11) n
O1 C2 C3 106.79(11) y
O1 C2 C1 110.40(11) y
C3 C2 C1 111.69(12) y
O1 C2 H21 112.7(9) n
C3 C2 H21 108.2(9) n
C1 C2 H21 107.1(9) n
C2 C3 C4 112.01(12) n
C2 C3 H31 109.2 n
C4 C3 H31 109.2 n
C2 C3 H32 109.2 n
C4 C3 H32 109.2 n
H31 C3 H32 107.9 n
C5 C4 C3 110.82(12) n
C5 C4 H41 109.5 n
C3 C4 H41 109.5 n
C5 C4 H42 109.5 n
C3 C4 H42 109.5 n
H41 C4 H42 108.1 n
C4 C5 C6 110.07(13) n
C4 C5 H51 109.6 n
C6 C5 H51 109.6 n
C4 C5 H52 109.6 n
C6 C5 H52 109.6 n
H51 C5 H52 108.2 n
C5 C6 C1 112.97(12) n
C5 C6 H61 109.0 n
C1 C6 H61 109.0 n
C5 C6 H62 109.0 n
C1 C6 H62 109.0 n
H61 C6 H62 107.8 n
O2 C7 N2 124.04(14) y
O2 C7 C1 119.39(12) y
N2 C7 C1 116.54(12) y
O1 C8 H8C 109.5 n
O1 C8 H8D 109.5 n
H8C C8 H8D 109.5 n
O1 C8 H8E 109.5 n
H8C C8 H8E 109.5 n
H8D C8 H8E 109.5 n
C11 N11 H11A 108.5(13) n
C11 N11 H11B 112.0(12) n
H11A N11 H11B 107.9(17) n
C11 N11 H11C 110.3(12) n
H11A N11 H11C 110.0(17) n
H11B N11 H11C 108.1(17) n
C17 N12 H12A 115.6(13) n
C17 N12 H12B 123.0(14) n
H12A N12 H12B 119.6(18) n
C12 O11 C18 113.83(12) n
N11 C11 C12 108.52(11) n
N11 C11 C16 109.72(11) n
C12 C11 C16 111.20(12) n
N11 C11 C17 104.02(11) n
C12 C11 C17 113.71(11) n
C16 C11 C17 109.40(11) n
O11 C12 C13 111.97(12) n
O11 C12 C11 105.79(11) n
C13 C12 C11 111.17(12) n
O11 C12 H121 107.5(12) n
C13 C12 H121 112.6(11) n
C11 C12 H121 107.4(11) n
C14 C13 C12 111.71(13) n
C14 C13 H131 109.3 n
C12 C13 H131 109.3 n
C14 C13 H132 109.3 n
C12 C13 H132 109.3 n
H131 C13 H132 107.9 n
C13 C14 C15 111.70(13) n
C13 C14 H141 109.3 n
C15 C14 H141 109.3 n
C13 C14 H142 109.3 n
C15 C14 H142 109.3 n
H141 C14 H142 107.9 n
C14 C15 C16 110.96(13) n
C14 C15 H151 109.4 n
C16 C15 H151 109.4 n
C14 C15 H152 109.4 n
C16 C15 H152 109.4 n
H151 C15 H152 108.0 n
C15 C16 C11 112.36(12) n
C15 C16 H161 109.1 n
C11 C16 H161 109.1 n
C15 C16 H162 109.1 n
C11 C16 H162 109.1 n
H161 C16 H162 107.9 n
O12 C17 N12 123.66(13) n
O12 C17 C11 118.98(12) n
N12 C17 C11 117.33(12) n
O11 C18 H181 109.5 n
O11 C18 H182 109.5 n
H181 C18 H182 109.5 n
O11 C18 H183 109.5 n
H181 C18 H183 109.5 n
H182 C18 H183 109.5 n
C21 N21 H21A 112.1(12) n
C21 N21 H21B 111.0(13) n
H21A N21 H21B 107.4(17) n
C21 N21 H21C 112.4(12) n
H21A N21 H21C 105.4(17) n
H21B N21 H21C 108.2(17) n
C27 N22 H22A 118.9(12) n
C27 N22 H22B 125.2(12) n
H22A N22 H22B 115.8(17) n
C28 O21 C22 114.09(11) n
N21 C21 C22 109.51(11) n
N21 C21 C26 108.85(11) n
C22 C21 C26 110.73(11) n
N21 C21 C27 105.13(11) n
C22 C21 C27 110.72(11) n
C26 C21 C27 111.72(11) n
O21 C22 C21 105.74(11) n
O21 C22 C23 113.46(12) n
C21 C22 C23 112.14(12) n
O21 C22 H221 111.5(10) n
C21 C22 H221 107.5(11) n
C23 C22 H221 106.4(10) n
C22 C23 C24 110.31(12) n
C22 C23 H231 109.6 n
C24 C23 H231 109.6 n
C22 C23 H232 109.6 n
C24 C23 H232 109.6 n
H231 C23 H232 108.1 n
C25 C24 C23 111.67(12) n
C25 C24 H241 109.3 n
C23 C24 H241 109.3 n
C25 C24 H242 109.3 n
C23 C24 H242 109.3 n
H241 C24 H242 107.9 n
C24 C25 C26 111.01(12) n
C24 C25 H251 109.4 n
C26 C25 H251 109.4 n
C24 C25 H252 109.4 n
C26 C25 H252 109.4 n
H251 C25 H252 108.0 n
C25 C26 C21 111.82(12) n
C25 C26 H261 109.3 n
C21 C26 H261 109.3 n
C25 C26 H262 109.3 n
C21 C26 H262 109.3 n
H261 C26 H262 107.9 n
O22 C27 N22 123.95(13) n
O22 C27 C21 119.70(12) n
N22 C27 C21 116.35(12) n
O21 C28 H281 109.5 n
O21 C28 H282 109.5 n
H281 C28 H282 109.5 n
O21 C28 H283 109.5 n
H281 C28 H283 109.5 n
H282 C28 H283 109.5 n
C31 N31 H31A 107.5(13) n
C31 N31 H31B 109.6(13) n
H31A N31 H31B 103.8(18) n
C31 N31 H31C 113.6(14) n
H31A N31 H31C 113.2(18) n
H31B N31 H31C 108.7(19) n
C37 N32 H32A 119.6(14) n
C37 N32 H32B 114.9(15) n
H32A N32 H32B 125(2) n
C32 O31 C38 113.90(12) n
N31 C31 C32 109.00(12) n
N31 C31 C36 109.12(12) n
C32 C31 C36 111.48(12) n
N31 C31 C37 104.41(11) n
C32 C31 C37 111.72(12) n
C36 C31 C37 110.83(12) n
O31 C32 C31 104.82(11) n
O31 C32 C33 112.40(12) n
C31 C32 C33 112.99(13) n
O31 C32 H321 110.5(11) n
C31 C32 H321 109.1(11) n
C33 C32 H321 107.0(11) n
C34 C33 C32 111.43(13) n
C34 C33 H331 109.3 n
C32 C33 H331 109.3 n
C34 C33 H332 109.3 n
C32 C33 H332 109.3 n
H331 C33 H332 108.0 n
C35 C34 C33 111.00(13) n
C35 C34 H341 109.4 n
C33 C34 H341 109.4 n
C35 C34 H342 109.4 n
C33 C34 H342 109.4 n
H341 C34 H342 108.0 n
C34 C35 C36 109.99(13) n
C34 C35 H351 109.7 n
C36 C35 H351 109.7 n
C34 C35 H352 109.7 n
C36 C35 H352 109.7 n
H351 C35 H352 108.2 n
C35 C36 C31 112.37(12) n
C35 C36 H361 109.1 n
C31 C36 H361 109.1 n
C35 C36 H362 109.1 n
C31 C36 H362 109.1 n
H361 C36 H362 107.9 n
O32 C37 N32 124.12(13) n
O32 C37 C31 118.82(12) n
N32 C37 C31 117.04(13) n
O31 C38 H381 109.5 n
O31 C38 H382 109.5 n
H381 C38 H382 109.5 n
O31 C38 H383 109.5 n
H381 C38 H383 109.5 n
H382 C38 H383 109.5 n
H411 O41 H412 102(3) n
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
N1 C1 . 1.5017(18) y
N1 H1A . 0.85(2) n
N1 H1B . 0.86(2) n
N1 H1C . 0.90(2) n
N2 C7 . 1.3249(19) y
N2 H2A . 0.84(2) n
N2 H2B . 0.73(2) n
O1 C8 . 1.419(2) y
O1 C2 . 1.4223(18) y
O2 C7 . 1.2297(17) y
C1 C7 . 1.5435(19) y
C1 C6 . 1.5442(19) n
C1 C2 . 1.545(2) n
C2 C3 . 1.525(2) n
C2 H21 . 1.015(16) n
C3 C4 . 1.527(2) n
C3 H31 . 0.9900 n
C3 H32 . 0.9900 n
C4 C5 . 1.518(2) n
C4 H41 . 0.9900 n
C4 H42 . 0.9900 n
C5 C6 . 1.534(2) n
C5 H51 . 0.9900 n
C5 H52 . 0.9900 n
C6 H61 . 0.9900 n
C6 H62 . 0.9900 n
C8 H8C . 0.9800 n
C8 H8D . 0.9800 n
C8 H8E . 0.9800 n
N11 C11 . 1.4949(18) y
N11 H11A . 0.90(2) n
N11 H11B . 0.91(2) n
N11 H11C . 0.94(2) n
N12 C17 . 1.3267(19) y
N12 H12A . 0.85(2) n
N12 H12B . 0.85(2) n
O11 C12 . 1.4185(19) n
O11 C18 . 1.4259(18) n
O12 C17 . 1.2319(18) y
C11 C12 . 1.5321(19) n
C11 C16 . 1.536(2) n
C11 C17 . 1.5450(19) n
C12 C13 . 1.531(2) n
C12 H121 . 0.933(19) n
C13 C14 . 1.525(3) n
C13 H131 . 0.9900 n
C13 H132 . 0.9900 n
C14 C15 . 1.527(2) n
C14 H141 . 0.9900 n
C14 H142 . 0.9900 n
C15 C16 . 1.531(2) n
C15 H151 . 0.9900 n
C15 H152 . 0.9900 n
C16 H161 . 0.9900 n
C16 H162 . 0.9900 n
C18 H181 . 0.9800 n
C18 H182 . 0.9800 n
C18 H183 . 0.9800 n
N21 C21 . 1.5052(17) y
N21 H21A . 0.93(2) n
N21 H21B . 0.88(2) n
N21 H21C . 0.88(2) n
N22 C27 . 1.3312(19) y
N22 H22A . 0.85(2) n
N22 H22B . 0.85(2) n
O21 C28 . 1.4177(18) n
O21 C22 . 1.4247(17) n
O22 C27 . 1.2310(18) y
C21 C22 . 1.531(2) n
C21 C26 . 1.5372(18) n
C21 C27 . 1.5493(18) n
C22 C23 . 1.5315(19) n
C22 H221 . 0.933(18) n
C23 C24 . 1.534(2) n
C23 H231 . 0.9900 n
C23 H232 . 0.9900 n
C24 C25 . 1.520(2) n
C24 H241 . 0.9900 n
C24 H242 . 0.9900 n
C25 C26 . 1.5330(19) n
C25 H251 . 0.9900 n
C25 H252 . 0.9900 n
C26 H261 . 0.9900 n
C26 H262 . 0.9900 n
C28 H281 . 0.9800 n
C28 H282 . 0.9800 n
C28 H283 . 0.9800 n
N31 C31 . 1.5039(18) y
N31 H31A . 0.91(2) n
N31 H31B . 0.94(2) n
N31 H31C . 0.87(2) n
N32 C37 . 1.325(2) y
N32 H32A . 0.86(2) n
N32 H32B . 0.82(2) n
O31 C32 . 1.4257(18) n
O31 C38 . 1.427(2) n
O32 C37 . 1.2376(18) y
C31 C32 . 1.530(2) n
C31 C36 . 1.5354(19) n
C31 C37 . 1.5503(19) n
C32 C33 . 1.535(2) n
C32 H321 . 0.953(19) n
C33 C34 . 1.529(2) n
C33 H331 . 0.9900 n
C33 H332 . 0.9900 n
C34 C35 . 1.523(2) n
C34 H341 . 0.9900 n
C34 H342 . 0.9900 n
C35 C36 . 1.531(2) n
C35 H351 . 0.9900 n
C35 H352 . 0.9900 n
C36 H361 . 0.9900 n
C36 H362 . 0.9900 n
C38 H381 . 0.9800 n
C38 H382 . 0.9800 n
C38 H383 . 0.9800 n
O41 H411 . 0.86(3) n
O41 H412 . 0.89(3) n
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
_geom_hbond_publ_flag
N1 H1A O32 . 0.85(2) 2.02(2) 2.862(2) 168.9(1.9) yes
N1 H1B Cl2 1_655 0.86(3) 2.32(2) 3.177(2) 171.8(1.7) yes
N1 H1C Cl1 . 0.90(2) 2.37(2) 3.222(2) 156.7(1.6) yes
N2 H2A O22 . 0.84(2) 2.16(2) 2.979(2) 163.5(2.0) y
N2 H2B Cl1 4_656 0.73(2) 2.64(2) 3.2820(10) 147.8(2.1) y
N11 H11A O41 4_546 0.90(2) 1.95(2) 2.746(2) 147.5(1.8) y
N11 H11B Cl2 4_546 0.91(2) 2.37(2) 3.136(2) 142.0(1.6) y
N11 H11C O2 4_646 0.94(2) 1.93(2) 2.763(2) 147.4(1.7) y
N12 H12B Cl2 . 0.85(2) 2.38(2) 3.203(2) 164.8(1.7) y
N21 H21B O12 . 0.88(2) 1.95(2) 2.791(2) 159.3(1.8) y
N21 H21A Cl4 2_554 0.93(2) 2.40(2) 3.285(2) 158.5(1.6) y
N21 H21C Cl3 3_556 0.88(2) 2.35(2) 3.219(2) 170.1(1.7) y
N22 H22A Cl1 4_656 0.85(2) 2.54(2) 3.388(2) 171.8(1.7) y
N22 H22B Cl3 . 0.85(2) 2.59(2) 3.430(2) 169.7(1.7) y
N31 H31B Cl4 3_557 0.94(2) 2.22(2) 3.1630(10) 176.6(1.8) y
N31 H31C Cl3 2_565 0.87(2) 2.31(2) 3.120(2) 155.1(1.9) y
N32 H32A Cl4 . 0.86(2) 2.50(2) 3.338(2) 163.2(1.8) y
N32 H32B Cl1 . 0.82(2) 2.50(2) 3.300(2) 163.7(1.9) y
O41 H411 Cl2 . 0.86(3) 2.62(3) 3.283(2) 135.1(2.3) y
O41 H412 Cl4 3_457 0.89(3) 2.27(2) 3.126(2) 163.3(2.9) 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
C7 C1 C2 H21 54.7(10) yes
N1 C1 C2 H21 171.8(10) yes
C17 C11 C12 H121 54.5(12) y
N11 C11 C12 H121 169.7(12) y
C27 C21 C22 H221 62.6(11) y
N21 C21 C22 H221 178.0(10) y
C37 C31 C32 H321 55.7(11) y
N31 C31 C32 H321 170.6(11) y
C8 O1 C2 C3 -156.25(12) n
C8 O1 C2 C1 82.13(15) y
N1 C1 C2 O1 48.74(14) y
C7 C1 C2 O1 -68.32(14) y
C6 C1 C2 O1 169.57(11) n
N1 C1 C2 C3 -69.93(14) n
C7 C1 C2 C3 173.02(11) n
C6 C1 C2 C3 50.90(15) n
O1 C2 C3 C4 -175.28(12) n
C1 C2 C3 C4 -54.48(16) n
C2 C3 C4 C5 58.00(17) n
C3 C4 C5 C6 -57.47(17) n
C4 C5 C6 C1 55.57(17) n
N1 C1 C6 C5 67.08(16) n
C7 C1 C6 C5 -177.72(13) n
C2 C1 C6 C5 -52.17(16) n
N1 C1 C7 O2 9.03(17) n
C6 C1 C7 O2 -109.08(15) n
C2 C1 C7 O2 127.13(14) n
N1 C1 C7 N2 -172.86(13) y
C6 C1 C7 N2 69.04(17) n
C2 C1 C7 N2 -54.75(16) n
C18 O11 C12 C13 -82.52(15) n
C18 O11 C12 C11 156.24(12) y
N11 C11 C12 O11 55.08(14) y
C16 C11 C12 O11 175.85(11) n
C17 C11 C12 O11 -60.14(15) y
N11 C11 C12 C13 -66.68(16) n
C16 C11 C12 C13 54.09(16) n
C17 C11 C12 C13 178.11(12) n
O11 C12 C13 C14 -173.38(13) n
C11 C12 C13 C14 -55.29(17) n
C12 C13 C14 C15 55.70(18) n
C13 C14 C15 C16 -54.54(18) n
C14 C15 C16 C11 53.98(17) n
N11 C11 C16 C15 66.05(15) n
C12 C11 C16 C15 -54.01(16) n
C17 C11 C16 C15 179.56(12) n
N11 C11 C17 O12 14.13(16) n
C12 C11 C17 O12 131.98(13) n
C16 C11 C17 O12 -103.03(15) n
N11 C11 C17 N12 -167.89(12) y
C12 C11 C17 N12 -50.04(17) n
C16 C11 C17 N12 74.95(15) n
C28 O21 C22 C21 168.13(12) y
C28 O21 C22 C23 -68.56(16) n
N21 C21 C22 O21 58.76(13) y
C26 C21 C22 O21 178.80(10) n
C27 C21 C22 O21 -56.72(14) y
N21 C21 C22 C23 -65.38(14) n
C26 C21 C22 C23 54.66(15) n
C27 C21 C22 C23 179.15(10) n
O21 C22 C23 C24 -175.29(12) n
C21 C22 C23 C24 -55.57(15) n
C22 C23 C24 C25 56.16(16) n
C23 C24 C25 C26 -56.11(16) n
C24 C25 C26 C21 55.03(16) n
N21 C21 C26 C25 66.40(16) n
C22 C21 C26 C25 -54.04(16) n
C27 C21 C26 C25 -177.95(12) n
N21 C21 C27 O22 -6.99(18) n
C22 C21 C27 O22 111.19(15) n
C26 C21 C27 O22 -124.89(14) n
N21 C21 C27 N22 172.73(12) y
C22 C21 C27 N22 -69.09(15) n
C26 C21 C27 N22 54.83(17) n
C38 O31 C32 C31 171.37(13) y
C38 O31 C32 C33 -65.53(17) n
N31 C31 C32 O31 52.18(14) y
C36 C31 C32 O31 172.70(11) n
C37 C31 C32 O31 -62.69(14) y
N31 C31 C32 C33 -70.54(15) n
C36 C31 C32 C33 49.98(16) n
C37 C31 C32 C33 174.59(11) n
O31 C32 C33 C34 -170.52(13) n
C31 C32 C33 C34 -52.13(17) n
C32 C33 C34 C35 56.24(18) n
C33 C34 C35 C36 -58.40(17) n
C34 C35 C36 C31 56.91(17) n
N31 C31 C36 C35 67.85(16) n
C32 C31 C36 C35 -52.60(17) n
C37 C31 C36 C35 -177.71(12) n
N31 C31 C37 O32 -2.77(18) n
C32 C31 C37 O32 114.89(15) n
C36 C31 C37 O32 -120.13(15) n
N31 C31 C37 N32 175.54(13) y
C32 C31 C37 N32 -66.80(17) n
C36 C31 C37 N32 58.18(18) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652238
