#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/18/2201813.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_2201813
loop_
_publ_author_name
'Beckmann, Claus'
'Jones, Peter G.'
'Kirby, Anthony J.'
_publ_section_title
;
 N,N,N',N'-Tetramethylstreptamine 2,4,6-orthoformate
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o564
_journal_page_last               o565
_journal_paper_doi               10.1107/S1600536803006275
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C11 H20 N2 O4'
_chemical_formula_moiety         'C11 H20 N2 O4'
_chemical_formula_sum            'C11 H20 N2 O4'
_chemical_formula_weight         244.29
_chemical_name_systematic
;
rac-(1s,3s,5R,6r,7S,8R,9S)-8,9-bis(dimethylamino)-
2,4,10-trioxatricyclo[3.3.1.1^3,7^]decan-6-ol
;
_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                100.386(10)
_cell_angle_beta                 104.367(8)
_cell_angle_gamma                105.528(6)
_cell_formula_units_Z            2
_cell_length_a                   6.9344(8)
_cell_length_b                   7.5439(10)
_cell_length_c                   12.1650(16)
_cell_measurement_reflns_used    62
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      3.5
_cell_volume                     572.85(13)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Fait, 1991)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Siemens P4'
_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  0.0155
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2719
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.15
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 297
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2598
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0587P)²+0.0004P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1011
_reflns_number_gt                1931
_reflns_number_total             2598
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6253.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (6 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2201813
_cod_database_fobs_code          2201813
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 0.6413(2) 0.92014(17) 0.32913(11) 0.0230(3) Uani d . 1 . . C
H1 0.7133 1.0037 0.4112 0.028 Uiso calc R 1 . . H
C3 0.6173(2) 0.90092(18) 0.13162(11) 0.0264(3) Uani d . 1 . . C
H3 0.6753 0.9718 0.0787 0.032 Uiso calc R 1 . . H
C5 0.3007(2) 0.76233(17) 0.17003(10) 0.0206(3) Uani d . 1 . . C
H5 0.1461 0.7425 0.1455 0.025 Uiso calc R 1 . . H
C6 0.4034(2) 0.88180(17) 0.29840(11) 0.0216(3) Uani d . 1 . . C
H6 0.3783 1.0071 0.3039 0.026 Uiso calc R 1 . . H
C7 0.57880(19) 0.61427(17) 0.18939(10) 0.0191(3) Uani d . 1 . . C
H7 0.6126 0.4928 0.1767 0.023 Uiso calc R 1 . . H
C8 0.33725(18) 0.56832(16) 0.14662(10) 0.0180(3) Uani d . 1 . . C
H8 0.2878 0.5131 0.0594 0.022 Uiso calc R 1 . . H
C9 0.69525(19) 0.73382(17) 0.31813(10) 0.0206(3) Uani d . 1 . . C
H9 0.8501 0.7671 0.3307 0.025 Uiso calc R 1 . . H
C11 0.6802(2) 0.4533(2) 0.39120(12) 0.0314(3) Uani d . 1 . . C
H11A 0.5782 0.3669 0.3172 0.038 Uiso calc R 1 . . H
H11B 0.6610 0.3992 0.4567 0.038 Uiso calc R 1 . . H
H11C 0.8235 0.4697 0.3879 0.038 Uiso calc R 1 . . H
C12 0.7873(2) 0.7560(2) 0.52656(12) 0.0326(3) Uani d . 1 . . C
H12A 0.7578 0.6896 0.5858 0.039 Uiso calc R 1 . . H
H12B 0.7630 0.8789 0.5430 0.039 Uiso calc R 1 . . H
H12C 0.9344 0.7777 0.5293 0.039 Uiso calc R 1 . . H
C13 0.0093(2) 0.4228(2) 0.18533(12) 0.0294(3) Uani d . 1 . . C
H13A 0.0113 0.5441 0.2319 0.035 Uiso calc R 1 . . H
H13B -0.0619 0.3180 0.2136 0.035 Uiso calc R 1 . . H
H13C -0.0664 0.4042 0.1024 0.035 Uiso calc R 1 . . H
C14 0.2128(2) 0.23498(18) 0.13637(13) 0.0297(3) Uani d . 1 . . C
H14A 0.1271 0.2038 0.0538 0.036 Uiso calc R 1 . . H
H14B 0.1481 0.1412 0.1740 0.036 Uiso calc R 1 . . H
H14C 0.3549 0.2324 0.1404 0.036 Uiso calc R 1 . . H
N1 0.64703(16) 0.63870(15) 0.40877(9) 0.0220(2) Uani d . 1 . . N
N2 0.22536(16) 0.42613(14) 0.19757(9) 0.0194(2) Uani d . 1 . . N
O2 0.71639(15) 1.01568(12) 0.24746(8) 0.0282(2) Uani d . 1 . . O
O4 0.39874(15) 0.86840(12) 0.09821(8) 0.0258(2) Uani d . 1 . . O
O10 0.66200(14) 0.72883(12) 0.11707(8) 0.0247(2) Uani d . 1 . . O
O1 0.31852(15) 0.79525(13) 0.37780(8) 0.0244(2) Uani d . 1 . . O
H01 0.372(3) 0.711(3) 0.3868(18) 0.062(6) 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'
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
O2 C1 C6 108.41(10) ?
O2 C1 C9 107.94(10) ?
C6 C1 C9 111.76(10) ?
O2 C1 H1 109.6 ?
C6 C1 H1 109.6 ?
C9 C1 H1 109.6 ?
O2 C3 O10 111.25(10) ?
O2 C3 O4 110.92(10) ?
O10 C3 O4 111.48(10) ?
O2 C3 H3 107.7 ?
O10 C3 H3 107.7 ?
O4 C3 H3 107.7 ?
O4 C5 C6 107.38(9) ?
O4 C5 C8 106.15(9) ?
C6 C5 C8 113.83(10) ?
O4 C5 H5 109.8 ?
C6 C5 H5 109.8 ?
C8 C5 H5 109.8 ?
O1 C6 C1 111.97(10) ?
O1 C6 C5 113.04(10) ?
C1 C6 C5 107.82(10) ?
O1 C6 H6 107.9 ?
C1 C6 H6 107.9 ?
C5 C6 H6 107.9 ?
O10 C7 C8 106.35(9) ?
O10 C7 C9 105.68(9) ?
C8 C7 C9 116.41(10) ?
O10 C7 H7 109.4 ?
C8 C7 H7 109.4 ?
C9 C7 H7 109.4 ?
N2 C8 C5 115.59(10) ?
N2 C8 C7 113.06(9) ?
C5 C8 C7 105.67(9) ?
N2 C8 H8 107.4 ?
C5 C8 H8 107.4 ?
C7 C8 H8 107.4 ?
N1 C9 C1 111.41(10) ?
N1 C9 C7 115.34(10) ?
C1 C9 C7 106.12(10) ?
N1 C9 H9 107.9 ?
C1 C9 H9 107.9 ?
C7 C9 H9 107.9 ?
N1 C11 H11A 109.5 ?
N1 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
N1 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
N1 C12 H12A 109.5 ?
N1 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
N1 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
N2 C13 H13A 109.5 ?
N2 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
N2 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
N2 C14 H14A 109.5 ?
N2 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
N2 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
C11 N1 C12 107.41(10) y
C11 N1 C9 111.14(10) y
C12 N1 C9 110.08(10) y
C13 N2 C14 106.91(10) y
C13 N2 C8 112.89(9) y
C14 N2 C8 109.32(10) y
C3 O2 C1 110.54(9) ?
C3 O4 C5 111.23(9) ?
C3 O10 C7 111.37(9) ?
C6 O1 H01 105.6(14) ?
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 O2 . 1.4464(14) ?
C1 C6 . 1.5308(18) ?
C1 C9 . 1.5403(17) ?
C1 H1 . 1.0000 ?
C3 O2 . 1.4030(16) ?
C3 O10 . 1.4045(15) ?
C3 O4 . 1.4076(16) ?
C3 H3 . 1.0000 ?
C5 O4 . 1.4566(14) ?
C5 C6 . 1.5346(17) ?
C5 C8 . 1.5401(16) ?
C5 H5 . 1.0000 ?
C6 O1 . 1.4176(15) ?
C6 H6 . 1.0000 ?
C7 O10 . 1.4536(14) ?
C7 C8 . 1.5454(16) ?
C7 C9 . 1.5464(17) ?
C7 H7 . 1.0000 ?
C8 N2 . 1.4729(14) y
C8 H8 . 1.0000 ?
C9 N1 . 1.4772(15) y
C9 H9 . 1.0000 ?
C11 N1 . 1.4639(17) y
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
C12 N1 . 1.4740(17) y
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C13 N2 . 1.4613(16) y
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C14 N2 . 1.4680(16) y
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
O1 H01 . 0.83(2) ?
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 H01 N1 . 0.83(2) 2.09(2) 2.8109(15) 145.8(19)
C13 H13B O2 1_445 0.98 2.55 3.5198(16) 170
C3 H3 O4 2_675 1.00 2.66 3.5442(16) 148
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
O2 C1 C6 O1 -177.51(9)
C9 C1 C6 O1 63.65(13)
O2 C1 C6 C5 57.54(12)
C9 C1 C6 C5 -61.30(12)
O4 C5 C6 O1 178.93(9)
C8 C5 C6 O1 -63.89(14)
O4 C5 C6 C1 -56.76(12)
C8 C5 C6 C1 60.43(13)
O4 C5 C8 N2 -171.75(9)
C6 C5 C8 N2 70.35(13)
O4 C5 C8 C7 62.42(11)
C6 C5 C8 C7 -55.48(13)
O10 C7 C8 N2 170.35(9)
C9 C7 C8 N2 -72.25(13)
O10 C7 C8 C5 -62.27(11)
C9 C7 C8 C5 55.13(12)
O2 C1 C9 N1 173.10(9)
C6 C1 C9 N1 -67.77(12)
O2 C1 C9 C7 -60.60(12)
C6 C1 C9 C7 58.52(12)
O10 C7 C9 N1 -175.63(9)
C8 C7 C9 N1 66.60(13)
O10 C7 C9 C1 60.49(11)
C8 C7 C9 C1 -57.27(13)
C1 C9 N1 C11 174.75(10)
C7 C9 N1 C11 53.70(14)
C1 C9 N1 C12 -66.39(13)
C7 C9 N1 C12 172.57(10)
C5 C8 N2 C13 41.44(14)
C7 C8 N2 C13 163.41(10)
C5 C8 N2 C14 160.30(10)
C7 C8 N2 C14 -77.74(12)
O10 C3 O2 C1 -61.52(13)
O4 C3 O2 C1 63.19(12)
C6 C1 O2 C3 -60.45(12)
C9 C1 O2 C3 60.78(12)
O2 C3 O4 C5 -63.43(12)
O10 C3 O4 C5 61.14(12)
C6 C5 O4 C3 59.94(12)
C8 C5 O4 C3 -62.16(12)
O2 C3 O10 C7 63.46(13)
O4 C3 O10 C7 -60.93(12)
C8 C7 O10 C3 61.70(12)
C9 C7 O10 C3 -62.62(12)
