#------------------------------------------------------------------------------
#$Date: 2016-03-25 12:19:48 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179810 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/06/7010670.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_7010670
loop_
_publ_author_name
'Batsanov, Andrei S.'
'Goeta, Andrés E.'
'Howard, Judith A. K.'
'Hughes, Andrew K.'
'Malget, John M.'
_publ_section_title
;
 The synthesis of closo- and nido-(aminoalkyl)dicarbaboranes: a
 re-examination of contradictory literature reports, crystal structure
 of [7-{H3N(CH2)3}-7,8-C2B9H11]·NH2NH2†
;
_journal_issue                   12
_journal_name_full
'Journal of the Chemical Society, Dalton Transactions'
_journal_page_first              1820
_journal_paper_doi               10.1039/b102009i
_journal_year                    2001
_chemical_formula_sum            'C18 H40 B9 N3 O3'
_chemical_formula_weight         443.82
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.43(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.430(2)
_cell_length_b                   23.019(5)
_cell_length_c                   12.140(3)
_cell_measurement_reflns_used    5510
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.4
_cell_volume                     2563.2(10)
_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      100(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'SMART 1K CCD area detector'
_diffrn_measurement_method       'ω 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  0.0665
_diffrn_reflns_av_sigmaI/netI    0.0567
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23620
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.77
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         5890
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0510
_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)+(0.0483P)²+1.3743P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1313
_reflns_number_gt                4005
_reflns_number_total             5890
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b102009i.txt
_cod_data_source_block           12b
_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 
;
_cod_original_cell_volume        2563(1)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7010670
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
O1 O 0.23264(15) 0.48218(6) 0.13143(11) 0.0294(3) Uani 1 1 d . . .
O2 O 0.27568(14) 0.57823(5) 0.34189(10) 0.0216(3) Uani 1 1 d . . .
O3 O 0.37439(16) 0.55939(6) 0.52371(11) 0.0314(3) Uani 1 1 d . . .
N1 N 0.45302(17) 0.47138(7) 0.25500(13) 0.0192(3) Uani 1 1 d . . .
H1N H 0.496(2) 0.4637(10) 0.325(2) 0.033(6) Uiso 1 1 d . . .
C1 C 0.57847(19) 0.38612(8) 0.11816(15) 0.0185(4) Uani 1 1 d . . .
H1 H 0.355(3) 0.3605(15) 0.102(3) 0.085(10) Uiso 1 1 d . . .
C2 C 0.5881(2) 0.33927(8) 0.21333(16) 0.0242(4) Uani 1 1 d . . .
H2 H 0.648(2) 0.3526(10) 0.2912(19) 0.034(6) Uiso 1 1 d . . .
C3 C 0.64700(19) 0.44524(8) 0.15331(15) 0.0200(4) Uani 1 1 d . . .
H31 H 0.6924 0.4598 0.0928 0.026 Uiso 1 1 d R . .
H32 H 0.7253 0.4405 0.2228 0.026 Uiso 1 1 d R . .
C4 C 0.5381(2) 0.49076(8) 0.17565(15) 0.0199(4) Uani 1 1 d . . .
H41 H 0.5921 0.5264 0.2059 0.026 Uiso 1 1 d R . .
H42 H 0.4705 0.5009 0.1029 0.026 Uiso 1 1 d R . .
C5 C 0.3075(2) 0.47001(8) 0.22683(15) 0.0200(4) Uani 1 1 d . . .
C6 C 0.30159(19) 0.54497(8) 0.42917(15) 0.0205(4) Uani 1 1 d . . .
C11 C 0.23287(19) 0.45086(8) 0.31814(15) 0.0202(4) Uani 1 1 d . . .
C12 C 0.23130(19) 0.48549(8) 0.41300(15) 0.0196(4) Uani 1 1 d . . .
C13 C 0.1541(2) 0.46610(9) 0.49140(16) 0.0240(4) Uani 1 1 d . . .
H13 H 0.1555 0.4884 0.5575 0.029 Uiso 1 1 d R . .
C14 C 0.0756(2) 0.41447(9) 0.47369(18) 0.0283(4) Uani 1 1 d . . .
H14 H 0.0203 0.4027 0.5259 0.034 Uiso 1 1 d R . .
C15 C 0.0777(2) 0.38016(9) 0.38026(18) 0.0286(5) Uani 1 1 d . . .
H15 H 0.0255 0.3445 0.3691 0.034 Uiso 1 1 d R . .
C16 C 0.1566(2) 0.39829(9) 0.30311(17) 0.0257(4) Uani 1 1 d . . .
H16 H 0.1587 0.3747 0.2393 0.031 Uiso 1 1 d R . .
B3 B 0.4498(2) 0.29468(9) 0.19563(17) 0.0204(4) Uani 1 1 d . . .
H3 H 0.412(2) 0.2729(9) 0.2653(18) 0.030(6) Uiso 1 1 d . . .
B4 B 0.3288(2) 0.31752(10) 0.06321(18) 0.0219(4) Uani 1 1 d . . .
H4 H 0.210(3) 0.3097(10) 0.0367(18) 0.037(6) Uiso 1 1 d . . .
B5 B 0.4262(2) 0.37952(9) 0.02445(19) 0.0229(4) Uani 1 1 d . . .
H5 H 0.371(2) 0.4178(10) -0.0229(18) 0.035(6) Uiso 1 1 d . . .
B6 B 0.7019(2) 0.33080(9) 0.12011(17) 0.0195(4) Uani 1 1 d . . .
H6 H 0.822(2) 0.3397(9) 0.1463(16) 0.023(5) Uiso 1 1 d . . .
B7 B 0.6171(2) 0.27001(9) 0.16633(18) 0.0209(4) Uani 1 1 d . . .
H7 H 0.686(2) 0.2388(9) 0.2201(16) 0.023(5) Uiso 1 1 d . . .
B8 B 0.4492(2) 0.25736(9) 0.06812(17) 0.0204(4) Uani 1 1 d . . .
H8 H 0.399(2) 0.2145(9) 0.0484(17) 0.028(6) Uiso 1 1 d . . .
B9 B 0.4319(2) 0.31179(9) -0.04240(17) 0.0207(4) Uani 1 1 d . . .
H9 H 0.376(2) 0.3017(9) -0.1310(18) 0.030(6) Uiso 1 1 d . . .
B10 B 0.5903(2) 0.35508(9) -0.00845(17) 0.0206(4) Uani 1 1 d . . .
H10 H 0.636(2) 0.3809(10) -0.0692(18) 0.034(6) Uiso 1 1 d . . .
B11 B 0.6070(2) 0.28015(9) 0.01941(17) 0.0210(4) Uani 1 1 d . . .
H11 H 0.664(2) 0.2524(9) -0.0301(17) 0.028(5) Uiso 1 1 d . . .
N2 N 0.46140(17) 0.66916(7) 0.38723(12) 0.0186(3) Uani 1 1 d . . .
H2N H 0.387(2) 0.6404(10) 0.3766(18) 0.030(6) Uiso 1 1 d . . .
C21 C 0.4887(2) 0.69128(9) 0.50545(15) 0.0278(5) Uani 1 1 d . . .
H211 H 0.5671 0.7202 0.5177 0.034(3) Uiso 1 1 d R . .
H212 H 0.5173 0.6589 0.5584 0.034(3) Uiso 1 1 d R . .
H213 H 0.3997 0.7093 0.5182 0.034(3) Uiso 1 1 d R . .
C22 C 0.4133(2) 0.71644(8) 0.30334(16) 0.0260(4) Uani 1 1 d . . .
H221 H 0.4911 0.7454 0.3104 0.035(4) Uiso 1 1 d R . .
H222 H 0.3257 0.7350 0.3176 0.035(4) Uiso 1 1 d R . .
H223 H 0.3912 0.7001 0.2267 0.035(4) Uiso 1 1 d R . .
C23 C 0.5918(2) 0.63870(9) 0.36634(18) 0.0291(5) Uani 1 1 d . . .
H231 H 0.5715 0.6252 0.2876 0.038(4) Uiso 1 1 d R . .
H232 H 0.6149 0.6053 0.4175 0.038(4) Uiso 1 1 d R . .
H233 H 0.6749 0.6654 0.3801 0.038(4) Uiso 1 1 d R . .
N3 N 0.03404(18) 0.58733(7) 0.16509(14) 0.0237(4) Uani 1 1 d . . .
H3N H 0.124(3) 0.5791(11) 0.207(2) 0.046(7) Uiso 1 1 d . . .
C31 C -0.0616(2) 0.53883(12) 0.1804(2) 0.0468(7) Uani 1 1 d . . .
H311 H -0.1602 0.5457 0.1343 0.072(5) Uiso 1 1 d R . .
H312 H -0.0647 0.5360 0.2603 0.072(5) Uiso 1 1 d R . .
H313 H -0.0235 0.5025 0.1565 0.072(5) Uiso 1 1 d R . .
C32 C 0.0425(3) 0.59163(11) 0.04559(19) 0.0409(6) Uani 1 1 d . . .
H321 H 0.0908 0.5570 0.0248 0.060(5) Uiso 1 1 d R . .
H322 H 0.0986 0.6263 0.0355 0.060(5) Uiso 1 1 d R . .
H323 H -0.0560 0.5946 -0.0029 0.060(5) Uiso 1 1 d R . .
C33 C -0.0180(4) 0.64235(12) 0.2051(2) 0.0770(12) Uani 1 1 d . . .
H331 H -0.1174 0.6504 0.1619 0.080(6) Uiso 1 1 d R . .
H332 H 0.0466 0.6741 0.1940 0.080(6) Uiso 1 1 d R . .
H333 H -0.0173 0.6391 0.2858 0.080(6) Uiso 1 1 d 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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
C5 N1 C4 121.87(15) . . ?
C3 C1 C2 117.37(15) . . ?
C3 C1 B5 121.99(15) . . ?
C2 C1 B5 110.09(15) . . ?
C3 C1 B6 114.53(15) . . ?
C2 C1 B6 63.75(12) . . ?
B5 C1 B6 115.26(15) . . ?
C3 C1 B10 120.62(15) . . ?
C2 C1 B10 111.57(15) . . ?
B5 C1 B10 64.17(12) . . ?
B6 C1 B10 61.42(11) . . ?
C1 C2 B3 115.30(15) . . ?
C1 C2 B7 112.10(14) . . ?
B3 C2 B7 64.00(13) . . ?
C1 C2 B6 62.43(12) . . ?
B3 C2 B6 115.95(15) . . ?
B7 C2 B6 61.06(12) . . ?
C1 C3 C4 113.66(15) . . ?
N1 C4 C3 113.64(15) . . ?
O1 C5 N1 124.21(18) . . ?
O1 C5 C11 119.33(17) . . ?
N1 C5 C11 116.45(15) . . ?
O3 C6 O2 124.30(18) . . ?
O3 C6 C12 119.63(16) . . ?
O2 C6 C12 116.01(15) . . ?
C16 C11 C12 119.71(17) . . ?
C16 C11 C5 118.05(17) . . ?
C12 C11 C5 122.14(16) . . ?
C13 C12 C11 118.91(17) . . ?
C13 C12 C6 118.79(17) . . ?
C11 C12 C6 122.16(16) . . ?
C14 C13 C12 120.66(19) . . ?
C15 C14 C13 120.38(19) . . ?
C14 C15 C16 119.48(19) . . ?
C15 C16 C11 120.80(19) . . ?
C2 B3 B8 105.09(15) . . ?
C2 B3 B7 60.78(12) . . ?
B8 B3 B7 59.70(12) . . ?
C2 B3 B4 104.62(15) . . ?
B8 B3 B4 59.57(12) . . ?
B7 B3 B4 108.50(15) . . ?
B8 B4 B9 61.16(12) . . ?
B8 B4 B5 105.19(15) . . ?
B9 B4 B5 58.64(12) . . ?
B8 B4 B3 58.81(11) . . ?
B9 B4 B3 106.19(15) . . ?
B5 B4 B3 101.80(15) . . ?
C1 B5 B9 106.84(15) . . ?
C1 B5 B10 60.74(12) . . ?
B9 B5 B10 59.72(12) . . ?
C1 B5 B4 108.12(15) . . ?
B9 B5 B4 59.75(12) . . ?
B10 B5 B4 109.18(15) . . ?
C1 B6 C2 53.82(11) . . ?
C1 B6 B10 59.29(11) . . ?
C2 B6 B10 102.06(15) . . ?
C1 B6 B7 103.63(14) . . ?
C2 B6 B7 59.31(12) . . ?
B10 B6 B7 108.16(15) . . ?
C1 B6 B11 104.22(14) . . ?
C2 B6 B11 103.48(15) . . ?
B10 B6 B11 59.68(12) . . ?
B7 B6 B11 60.34(12) . . ?
C2 B7 B6 59.64(12) . . ?
C2 B7 B8 100.84(14) . . ?
B6 B7 B8 108.44(14) . . ?
C2 B7 B11 103.49(14) . . ?
B6 B7 B11 60.03(12) . . ?
B8 B7 B11 61.01(12) . . ?
C2 B7 B3 55.22(11) . . ?
B6 B7 B3 107.28(15) . . ?
B8 B7 B3 59.62(12) . . ?
B11 B7 B3 108.28(14) . . ?
B3 B8 B7 60.68(12) . . ?
B3 B8 B4 61.62(12) . . ?
B7 B8 B4 110.95(15) . . ?
B3 B8 B11 108.10(15) . . ?
B7 B8 B11 59.73(12) . . ?
B4 B8 B11 109.33(15) . . ?
B3 B8 B9 107.03(15) . . ?
B7 B8 B9 107.29(15) . . ?
B4 B8 B9 59.46(12) . . ?
B11 B8 B9 59.75(12) . . ?
B10 B9 B5 60.49(12) . . ?
B10 B9 B4 111.32(15) . . ?
B5 B9 B4 61.61(13) . . ?
B10 B9 B11 59.08(12) . . ?
B5 B9 B11 106.76(14) . . ?
B4 B9 B11 109.28(14) . . ?
B10 B9 B8 106.93(14) . . ?
B5 B9 B8 106.09(15) . . ?
B4 B9 B8 59.38(12) . . ?
B11 B9 B8 59.77(12) . . ?
C1 B10 B11 104.90(14) . . ?
C1 B10 B6 59.28(11) . . ?
B11 B10 B6 60.59(12) . . ?
C1 B10 B9 102.50(14) . . ?
B11 B10 B9 61.57(12) . . ?
B6 B10 B9 109.15(15) . . ?
C1 B10 B5 55.09(11) . . ?
B11 B10 B5 108.16(15) . . ?
B6 B10 B5 105.91(15) . . ?
B9 B10 B5 59.79(12) . . ?
B10 B11 B6 59.73(12) . . ?
B10 B11 B7 107.64(15) . . ?
B6 B11 B7 59.63(12) . . ?
B10 B11 B9 59.36(12) . . ?
B6 B11 B9 106.74(15) . . ?
B7 B11 B9 107.50(15) . . ?
B10 B11 B8 107.73(15) . . ?
B6 B11 B8 106.74(15) . . ?
B7 B11 B8 59.26(12) . . ?
B9 B11 B8 60.48(12) . . ?
C23 N2 C22 111.17(15) . . ?
C23 N2 C21 111.16(15) . . ?
C22 N2 C21 111.52(15) . . ?
C31 N3 C32 110.44(18) . . ?
C31 N3 C33 110.3(2) . . ?
C32 N3 C33 111.30(19) . . ?
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
O1 C5 1.240(2) . ?
O2 C6 1.284(2) . ?
O3 C6 1.238(2) . ?
N1 C5 1.335(2) . ?
N1 C4 1.459(2) . ?
C1 C3 1.524(2) . ?
C1 C2 1.568(3) . ?
C1 B5 1.619(3) . ?
C1 B6 1.722(3) . ?
C1 B10 1.722(3) . ?
C2 B3 1.634(3) . ?
C2 B7 1.736(3) . ?
C2 B6 1.742(3) . ?
C3 C4 1.535(3) . ?
C5 C11 1.510(3) . ?
C6 C12 1.514(3) . ?
C11 C16 1.398(3) . ?
C11 C12 1.403(3) . ?
C12 C13 1.399(3) . ?
C13 C14 1.390(3) . ?
C14 C15 1.386(3) . ?
C15 C16 1.389(3) . ?
B3 B8 1.769(3) . ?
B3 B7 1.788(3) . ?
B3 B4 1.820(3) . ?
B4 B8 1.783(3) . ?
B4 B9 1.785(3) . ?
B4 B5 1.817(3) . ?
B5 B9 1.764(3) . ?
B5 B10 1.776(3) . ?
B6 B10 1.759(3) . ?
B6 B7 1.767(3) . ?
B6 B11 1.774(3) . ?
B7 B8 1.771(3) . ?
B7 B11 1.779(3) . ?
B8 B11 1.802(3) . ?
B8 B9 1.815(3) . ?
B9 B10 1.763(3) . ?
B9 B11 1.802(3) . ?
B10 B11 1.758(3) . ?
N2 C23 1.487(2) . ?
N2 C22 1.488(2) . ?
N2 C21 1.488(2) . ?
N3 C31 1.474(3) . ?
N3 C32 1.475(3) . ?
N3 C33 1.481(3) . ?
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 H1N O3 0.87(2) 2.03(2) 2.887(2) 170(2) 3_666
N2 H2N O2 0.95(2) 1.77(2) 2.702(2) 167(2) .
N3 H3N O2 0.90(3) 1.91(3) 2.751(2) 155(2) .
