#------------------------------------------------------------------------------
#$Date: 2016-02-16 02:10:39 +0100 (mar 16 de feb de 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/38/7203897.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_7203897
loop_
_publ_author_name
'von Hirschheydt, Thomas'
'Wolfart, Volker'
'Gleiter, Rolf'
'Irngartinger, Hermann'
'Oeser, Thomas'
'Rominger, Frank'
'Eisenträger, Frank'
_publ_section_title
;
 A short survey of bicyclic diamines -- syntheses and
 properties of N,N'-bridged-1,10-diazabicyclooctadeca-5,14-diynes
;
_journal_issue                   2
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              175
_journal_paper_doi               10.1039/a907609c
_journal_year                    2000
_chemical_formula_sum            'C19 H35.5 N2 O4.06'
_chemical_formula_weight         356.91
_chemical_name_systematic
;

 (35)

;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.3480(10)
_cell_angle_beta                 93.019(2)
_cell_angle_gamma                102.1370(10)
_cell_formula_units_Z            4
_cell_length_a                   11.1299(9)
_cell_length_b                   12.4995(10)
_cell_length_c                   15.5200(13)
_cell_measurement_temperature    200(2)
_cell_volume                     2059.6(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.882
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0581
_diffrn_reflns_av_sigmaI/netI    0.1010
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15475
_diffrn_reflns_theta_full        25.61
_diffrn_reflns_theta_max         25.61
_diffrn_reflns_theta_min         1.34
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.58
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             784
_exptl_crystal_size_max          .31
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .06
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    ride
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         6862
_refine_ls_number_restraints     55
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1538
_refine_ls_R_factor_gt           0.0613
_refine_ls_shift/su_max          2.691
_refine_ls_shift/su_mean         0.068
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0671P)²+0.3960P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1659
_reflns_number_gt                3358
_reflns_number_total             6862
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            a907609c.txt
_cod_data_source_block           th16
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 
;
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C19 H35.50 N2 O4.06'
_cod_database_code               7203897
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6837(2) -0.1982(2) 0.48876(16) 0.0280(6) Uani 1 1 d . . .
C2 C 0.7694(3) -0.2687(3) 0.4542(2) 0.0367(9) Uani 1 1 d . . .
H2A H 0.7829 -0.2611 0.3930 0.044 Uiso 1 1 calc R . .
H2B H 0.7304 -0.3481 0.4523 0.044 Uiso 1 1 calc R . .
C3 C 0.8940(3) -0.2385(3) 0.5091(2) 0.0403(9) Uani 1 1 d . . .
H3A H 0.8912 -0.2858 0.5535 0.048 Uiso 1 1 calc R . .
H3B H 0.9100 -0.1594 0.5412 0.048 Uiso 1 1 calc R . .
C4 C 1.0003(3) -0.2548(3) 0.4523(2) 0.0370(9) Uani 1 1 d . . .
H4A H 1.0762 -0.2453 0.4919 0.044 Uiso 1 1 calc R . .
H4B H 0.9806 -0.3325 0.4170 0.044 Uiso 1 1 calc R . .
C5 C 1.0256(3) -0.1769(3) 0.3918(2) 0.0343(9) Uani 1 1 d . . .
C6 C 1.0493(3) -0.1182(3) 0.3403(2) 0.0360(9) Uani 1 1 d . . .
C7 C 1.0881(3) -0.0517(3) 0.2739(2) 0.0404(9) Uani 1 1 d . . .
H7A H 1.0857 -0.1038 0.2165 0.048 Uiso 1 1 calc R . .
H7B H 1.1749 -0.0105 0.2911 0.048 Uiso 1 1 calc R . .
C8 C 1.0108(3) 0.0327(3) 0.2608(2) 0.0352(9) Uani 1 1 d . . .
H8A H 1.0156 0.0869 0.3174 0.042 Uiso 1 1 calc R . .
H8B H 1.0472 0.0750 0.2172 0.042 Uiso 1 1 calc R . .
C9 C 0.8750(3) -0.0199(3) 0.2292(2) 0.0353(9) Uani 1 1 d . . .
H9A H 0.8631 -0.0285 0.1643 0.042 Uiso 1 1 calc R . .
H9B H 0.8540 -0.0957 0.2422 0.042 Uiso 1 1 calc R . .
N10 N 0.7892(2) 0.0458(2) 0.27027(16) 0.0297(7) Uani 1 1 d . . .
C11 C 0.6656(3) 0.0032(3) 0.2198(2) 0.0327(8) Uani 1 1 d . . .
H11A H 0.6361 -0.0766 0.2221 0.039 Uiso 1 1 calc R . .
H11B H 0.6741 0.0069 0.1572 0.039 Uiso 1 1 calc R . .
C12 C 0.5676(3) 0.0666(3) 0.2530(2) 0.0373(9) Uani 1 1 d . . .
H12A H 0.5748 0.1337 0.2269 0.045 Uiso 1 1 calc R . .
H12B H 0.5825 0.0922 0.3179 0.045 Uiso 1 1 calc R . .
C13 C 0.4363(3) -0.0073(3) 0.2284(2) 0.0405(9) Uani 1 1 d . . .
H13A H 0.3764 0.0414 0.2304 0.049 Uiso 1 1 calc R . .
H13B H 0.4301 -0.0510 0.1671 0.049 Uiso 1 1 calc R . .
C14 C 0.4037(3) -0.0846(3) 0.2879(2) 0.0356(9) Uani 1 1 d . . .
C15 C 0.3787(3) -0.1422(3) 0.3400(2) 0.0343(9) Uani 1 1 d . . .
C16 C 0.3489(3) -0.2098(3) 0.4076(2) 0.0371(9) Uani 1 1 d . . .
H16A H 0.3254 -0.2901 0.3784 0.045 Uiso 1 1 calc R . .
H16B H 0.2770 -0.1901 0.4366 0.045 Uiso 1 1 calc R . .
C17 C 0.4576(3) -0.1911(3) 0.4784(2) 0.0362(9) Uani 1 1 d . . .
H17A H 0.4935 -0.1098 0.4980 0.043 Uiso 1 1 calc R . .
H17B H 0.4268 -0.2195 0.5302 0.043 Uiso 1 1 calc R . .
C18 C 0.5583(3) -0.2501(3) 0.4440(2) 0.0316(8) Uani 1 1 d . . .
H18A H 0.5360 -0.3288 0.4508 0.038 Uiso 1 1 calc R . .
H18B H 0.5602 -0.2513 0.3801 0.038 Uiso 1 1 calc R . .
C19 C 0.7271(3) -0.0826(3) 0.4759(2) 0.0320(8) Uani 1 1 d . . .
H19A H 0.8154 -0.0558 0.4985 0.038 Uiso 1 1 calc R . .
H19B H 0.6806 -0.0334 0.5114 0.038 Uiso 1 1 calc R . .
C20 C 0.7127(3) -0.0712(3) 0.3803(2) 0.0398(9) Uani 1 1 d . . .
H20A H 0.7411 -0.1328 0.3425 0.048 Uiso 1 1 calc R . .
H20B H 0.6240 -0.0798 0.3621 0.048 Uiso 1 1 calc R . .
C21 C 0.7837(3) 0.0392(3) 0.3647(2) 0.0332(8) Uani 1 1 d . . .
H21A H 0.7455 0.0995 0.3945 0.040 Uiso 1 1 calc R . .
H21B H 0.8692 0.0538 0.3928 0.040 Uiso 1 1 calc R . .
N31 N 0.7603(2) 0.5496(2) 0.15681(16) 0.0288(6) Uani 1 1 d . . .
C32 C 0.8789(3) 0.6058(3) 0.2088(2) 0.0368(9) Uani 1 1 d . . .
H32A H 0.8656 0.6181 0.2722 0.044 Uiso 1 1 calc R . .
H32B H 0.9066 0.6803 0.1944 0.044 Uiso 1 1 calc R . .
C33 C 0.9817(3) 0.5427(3) 0.1940(2) 0.0440(10) Uani 1 1 d . . .
H33A H 0.9666 0.4951 0.1338 0.053 Uiso 1 1 calc R . .
H33B H 0.9793 0.4929 0.2365 0.053 Uiso 1 1 calc R . .
C34 C 1.1104(3) 0.6203(3) 0.2049(2) 0.0414(9) Uani 1 1 d . . .
H34A H 1.1205 0.6754 0.2616 0.050 Uiso 1 1 calc R . .
H34B H 1.1731 0.5752 0.2080 0.050 Uiso 1 1 calc R . .
C35 C 1.1341(3) 0.6813(3) 0.1331(3) 0.0393(9) Uani 1 1 d . . .
C36 C 1.1573(3) 0.7313(3) 0.0754(3) 0.0417(9) Uani 1 1 d . . .
C37 C 1.1924(3) 0.7948(3) 0.0068(2) 0.0460(10) Uani 1 1 d . . .
H37A H 1.2639 0.7710 -0.0199 0.055 Uiso 1 1 calc R . .
H37B H 1.2194 0.8752 0.0352 0.055 Uiso 1 1 calc R . .
C38 C 1.0900(3) 0.7809(3) -0.0667(2) 0.0403(9) Uani 1 1 d . . .
H38A H 1.0596 0.7002 -0.0932 0.048 Uiso 1 1 calc R . .
H38B H 1.1249 0.8182 -0.1134 0.048 Uiso 1 1 calc R . .
C39 C 0.9810(3) 0.8295(3) -0.0350(2) 0.0354(9) Uani 1 1 d . . .
H39A H 0.9794 0.8323 0.0291 0.042 Uiso 1 1 calc R . .
H39B H 0.9941 0.9073 -0.0437 0.042 Uiso 1 1 calc R . .
N40 N 0.8596(2) 0.7652(2) -0.08075(17) 0.0308(7) Uani 1 1 d . . .
C41 C 0.7664(3) 0.8319(3) -0.0581(2) 0.0344(8) Uani 1 1 d . . .
H41A H 0.7957 0.9065 -0.0720 0.041 Uiso 1 1 calc R . .
H41B H 0.7608 0.8436 0.0064 0.041 Uiso 1 1 calc R . .
C42 C 0.6372(3) 0.7807(3) -0.1051(2) 0.0395(9) Uani 1 1 d . . .
H42A H 0.6223 0.6981 -0.1153 0.047 Uiso 1 1 calc R . .
H42B H 0.6326 0.8013 -0.1634 0.047 Uiso 1 1 calc R . .
C43 C 0.5360(3) 0.8199(3) -0.0523(2) 0.0428(9) Uani 1 1 d . . .
H43A H 0.5615 0.9019 -0.0296 0.051 Uiso 1 1 calc R . .
H43B H 0.4592 0.8044 -0.0922 0.051 Uiso 1 1 calc R . .
C44 C 0.5107(3) 0.7647(3) 0.0223(2) 0.0368(9) Uani 1 1 d . . .
C45 C 0.4874(3) 0.7145(3) 0.0793(2) 0.0337(9) Uani 1 1 d . . .
C46 C 0.4560(3) 0.6467(3) 0.1464(2) 0.0373(9) Uani 1 1 d . . .
H46A H 0.3676 0.6084 0.1351 0.045 Uiso 1 1 calc R . .
H46B H 0.4687 0.6971 0.2055 0.045 Uiso 1 1 calc R . .
C47 C 0.5341(3) 0.5583(3) 0.1466(2) 0.0346(8) Uani 1 1 d . . .
H47A H 0.4945 0.5023 0.1796 0.042 Uiso 1 1 calc R . .
H47B H 0.5369 0.5187 0.0851 0.042 Uiso 1 1 calc R . .
C48 C 0.6655(3) 0.6114(3) 0.1887(2) 0.0329(8) Uani 1 1 d . . .
H48A H 0.6889 0.6880 0.1776 0.039 Uiso 1 1 calc R . .
H48B H 0.6663 0.6182 0.2533 0.039 Uiso 1 1 calc R . .
C49 C 0.7698(3) 0.5424(3) 0.0612(2) 0.0324(8) Uani 1 1 d . . .
H49A H 0.6929 0.4937 0.0280 0.039 Uiso 1 1 calc R . .
H49B H 0.8389 0.5069 0.0438 0.039 Uiso 1 1 calc R . .
C50 C 0.7908(4) 0.6561(3) 0.0352(2) 0.0528(11) Uani 1 1 d . . .
H50A H 0.7147 0.6849 0.0418 0.063 Uiso 1 1 calc R . .
H50B H 0.8576 0.7093 0.0765 0.063 Uiso 1 1 calc R . .
C51 C 0.8246(3) 0.6532(3) -0.0576(2) 0.0375(9) Uani 1 1 d . . .
H51A H 0.8946 0.6160 -0.0662 0.045 Uiso 1 1 calc R . .
H51B H 0.7536 0.6070 -0.0990 0.045 Uiso 1 1 calc R . .
O1 O 0.8621(2) 0.6874(2) -0.26386(15) 0.0430(7) Uani 1 1 d D . .
H1C H 0.815(3) 0.627(2) -0.292(2) 0.065 Uiso 1 1 d D . .
H1D H 0.870(3) 0.714(3) -0.2084(15) 0.065 Uiso 1 1 d D . .
O2 O 0.8860(2) 0.2810(2) 0.29992(18) 0.0469(7) Uani 1 1 d D . .
H2C H 0.962(2) 0.298(3) 0.286(2) 0.070 Uiso 1 1 d D . .
H2D H 0.850(3) 0.2099(19) 0.290(3) 0.070 Uiso 1 1 d D . .
O3 O 0.6743(2) -0.2151(2) 0.66551(17) 0.0507(7) Uani 1 1 d D . .
H3C H 0.732(3) -0.250(3) 0.676(3) 0.076 Uiso 1 1 d D . .
H3D H 0.672(4) -0.210(3) 0.6096(16) 0.076 Uiso 1 1 d D . .
O4 O 0.6921(2) 0.3459(2) 0.21124(19) 0.0555(8) Uani 1 1 d D . .
H4C H 0.755(3) 0.333(3) 0.239(3) 0.083 Uiso 1 1 d D . .
H4D H 0.723(3) 0.409(2) 0.195(3) 0.083 Uiso 1 1 d D . .
O5 O 0.4694(3) -0.3876(3) 0.6632(2) 0.0735(9) Uani 1 1 d D . .
H5C H 0.421(4) -0.417(4) 0.618(2) 0.110 Uiso 1 1 d D . .
H5D H 0.521(4) -0.325(3) 0.672(3) 0.110 Uiso 1 1 d D . .
O6 O 0.6656(3) 0.4999(3) -0.3298(3) 0.1006(12) Uani 1 1 d D . .
H6C H 0.712(5) 0.500(5) -0.379(3) 0.151 Uiso 1 1 d D . .
O7 O 1.3201(7) 0.5404(4) 0.5060(3) 0.167(4) Uani 0.927(14) 1 d P . .
O8 O 1.0843(6) 0.5406(4) 0.5610(3) 0.133(3) Uani 0.868(10) 1 d P . .
O9 O 1.212(2) 0.5743(12) 0.5411(10) 0.116(8) Uiso 0.309(14) 1 d P . .
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'
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
C18 N1 C19 111.6(2) . . ?
C18 N1 C2 108.9(2) . . ?
C19 N1 C2 110.4(2) . . ?
N1 C2 C3 113.5(3) . . ?
C2 C3 C4 112.3(3) . . ?
C5 C4 C3 114.4(3) . . ?
C6 C5 C4 176.4(3) . . ?
C5 C6 C7 174.3(3) . . ?
C6 C7 C8 115.6(3) . . ?
C9 C8 C7 114.2(3) . . ?
N10 C9 C8 113.7(3) . . ?
C9 N10 C11 108.8(2) . . ?
C9 N10 C21 110.5(2) . . ?
C11 N10 C21 111.4(2) . . ?
N10 C11 C12 114.7(3) . . ?
C11 C12 C13 111.6(3) . . ?
C14 C13 C12 112.4(3) . . ?
C15 C14 C13 176.3(4) . . ?
C14 C15 C16 177.7(4) . . ?
C15 C16 C17 112.5(3) . . ?
C18 C17 C16 112.1(3) . . ?
N1 C18 C17 114.7(3) . . ?
N1 C19 C20 114.2(3) . . ?
C21 C20 C19 113.6(3) . . ?
N10 C21 C20 115.0(3) . . ?
C32 N31 C49 111.4(2) . . ?
C32 N31 C48 108.5(2) . . ?
C49 N31 C48 111.5(2) . . ?
N31 C32 C33 115.0(3) . . ?
C32 C33 C34 113.1(3) . . ?
C35 C34 C33 113.9(3) . . ?
C36 C35 C34 178.0(3) . . ?
C35 C36 C37 177.0(4) . . ?
C36 C37 C38 114.7(3) . . ?
C37 C38 C39 113.4(3) . . ?
N40 C39 C38 114.0(3) . . ?
C41 N40 C39 108.7(2) . . ?
C41 N40 C51 111.6(2) . . ?
C39 N40 C51 111.3(2) . . ?
N40 C41 C42 115.3(3) . . ?
C41 C42 C43 112.5(3) . . ?
C44 C43 C42 112.8(3) . . ?
C45 C44 C43 176.3(4) . . ?
C44 C45 C46 177.0(4) . . ?
C45 C46 C47 112.9(3) . . ?
C48 C47 C46 111.7(3) . . ?
N31 C48 C47 115.2(3) . . ?
N31 C49 C50 113.4(3) . . ?
C51 C50 C49 114.0(3) . . ?
N40 C51 C50 114.7(3) . . ?
O8 O9 O7 147.8(11) . . ?
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
N1 C18 1.480(4) . ?
N1 C19 1.481(4) . ?
N1 C2 1.482(4) . ?
C2 C3 1.523(4) . ?
C3 C4 1.536(4) . ?
C4 C5 1.477(5) . ?
C5 C6 1.191(4) . ?
C6 C7 1.474(5) . ?
C7 C8 1.530(4) . ?
C8 C9 1.528(4) . ?
C9 N10 1.477(4) . ?
N10 C11 1.485(4) . ?
N10 C21 1.488(4) . ?
C11 C12 1.531(4) . ?
C12 C13 1.539(4) . ?
C13 C14 1.469(5) . ?
C14 C15 1.192(4) . ?
C15 C16 1.481(5) . ?
C16 C17 1.538(4) . ?
C17 C18 1.529(4) . ?
C19 C20 1.520(4) . ?
C20 C21 1.511(4) . ?
N31 C32 1.471(4) . ?
N31 C49 1.480(4) . ?
N31 C48 1.483(4) . ?
C32 C33 1.523(4) . ?
C33 C34 1.532(4) . ?
C34 C35 1.475(5) . ?
C35 C36 1.199(5) . ?
C36 C37 1.469(5) . ?
C37 C38 1.527(4) . ?
C38 C39 1.529(4) . ?
C39 N40 1.481(4) . ?
N40 C41 1.476(4) . ?
N40 C51 1.491(4) . ?
C41 C42 1.526(4) . ?
C42 C43 1.533(4) . ?
C43 C44 1.471(5) . ?
C44 C45 1.190(4) . ?
C45 C46 1.479(5) . ?
C46 C47 1.544(4) . ?
C47 C48 1.525(4) . ?
C49 C50 1.527(4) . ?
C50 C51 1.503(4) . ?
O7 O9 1.455(17) . ?
O8 O9 1.46(2) . ?
