#------------------------------------------------------------------------------
#$Date: 2016-02-16 18:55:33 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176466 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/17/8101709.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_8101709
loop_
_publ_author_name
'R. Wartchow'
'S. Roeper'
'H. M. R. Hoffmann'
_publ_section_title
;
Crystal structures of ethanol hemisolvates of (1S,3R,4S,8S,9R)-1N-
boranyl-6'-methoxy-cinchonan-9-ol, C₂₀H₂₇BN₂O₂ · 
½C₂H₅OH, and (1S,3S,4S,8S,9R)-1N-boranyl-10,11-didehydro-6'-methoxy-
cinchonan-9-ol, C₂₀H₂₅BN₂O₂ · ½C₂H₅OH
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              89
_journal_page_last               92
_journal_volume                  220
_journal_year                    2005
_chemical_compound_source        'synthetic starting from a natural product'
_chemical_formula_moiety         'C20 H25 B N2 O2 , 0.5(C2 H6 O)'
_chemical_formula_sum            'C21 H28 B N2 O2.5'
_chemical_formula_weight         359.26
_chemical_name_common
'10,11-Didehydroquinineborane ethanol hemisolvate'
_chemical_name_systematic
;    
(1S,3S,4S,8S,9R)-1N-Boranyl-10,11-didehydro-6'-methoxy-cinchonan-9-ol 
ethanol hemisolvate
;
_space_group_IT_number           146
_symmetry_cell_setting           trigonal
_symmetry_Int_Tables_number      146
_symmetry_space_group_name_Hall  'R 3'
_symmetry_space_group_name_H-M   'R 3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            9
_cell_length_a                   26.465(6)
_cell_length_b                   26.465(6)
_cell_length_c                   7.375(2)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      24.75
_cell_measurement_theta_min      2.65
_cell_volume                     4473.4(19)
_computing_cell_refinement       'Stoe IPDS software'
_computing_data_collection       'Stoe IPDS software'
_computing_data_reduction        'Stoe IPDS software and SHELXL-93'
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material
;
 The first CIF was issued by SHELXL-93.
 The edited CIF is finally treated with the program CIF2SX 
 written by L. Farrugia, Univ. of Glasgow (1997) 
 and a refinement cycle is repeated to assure that 
 essential parameters were not changed. 
;
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_max 1.0
_diffrn_measurement_device       'Stoe IPDS area detector diffractometer'
_diffrn_measurement_method       '240 exposures, Δ φ 1.5 °'
_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  0.0684
_diffrn_reflns_av_sigmaI/netI    0.0803
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            21380
_diffrn_reflns_theta_max         26.06
_diffrn_reflns_theta_min         2.67
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  1.0
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_description       'hexagonal prism'
_exptl_crystal_F_000             1737
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.38(131)
_refine_ls_extinction_coef       0.00055(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.088
_refine_ls_goodness_of_fit_ref   1.475
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3874
_refine_ls_number_restraints     58
_refine_ls_restrained_S_all      1.086
_refine_ls_restrained_S_obs      1.461
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/esd_mean        0.000
_refine_ls_shift/su_max          -0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.01P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0654
_refine_ls_wR_factor_ref         0.0620
_reflns_number_gt                2033
_reflns_number_total             3874
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-1444.cff
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'R 3'
_cod_original_formula_sum        'C21 H28 B N2 O2.50'
_cod_database_code               8101709
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
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_thermal_displace_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
O1 O 0.18561(7) 0.28709(7) 0.5294(11) 0.0539(5) Uani 1 9 b d D .
H1 H 0.2063(13) 0.3047(13) 0.6460(29) 0.125(14) Uiso 1 9 b d D .
B1 B 0.1054(2) 0.1384(2) 0.8175(12) 0.0923(14) Uiso 1 9 b d . .
H2 H 0.1142(2) 0.1093(2) 0.7758(12) 0.138 Uiso 1 9 b calc R .
H3 H 0.0755(2) 0.1219(2) 0.9083(12) 0.138 Uiso 1 9 b calc R .
H4 H 0.1399(2) 0.1706(2) 0.8685(12) 0.138 Uiso 1 9 b calc R .
N1 N 0.08295(8) 0.16124(9) 0.6485(12) 0.0529(6) Uani 1 9 b d . .
C2 C 0.02800(10) 0.10942(11) 0.5808(12) 0.0561(8) Uani 1 9 b d . .
H5 H 0.00269(10) 0.08930(11) 0.6827(12) 0.067 Uiso 1 9 b calc R .
H6 H 0.03755(10) 0.08255(11) 0.5214(12) 0.067 Uiso 1 9 b calc R .
C3 C -0.00412(11) 0.12761(12) 0.4476(12) 0.0624(9) Uani 1 9 b d . .
H7 H -0.03609(11) 0.12824(12) 0.5126(12) 0.075 Uiso 1 9 b calc R .
C4 C 0.03928(12) 0.19010(12) 0.3865(12) 0.0663(9) Uani 1 9 b d . .
H8 H 0.02278(12) 0.20160(12) 0.2864(12) 0.080 Uiso 1 9 b calc R .
C5 C 0.05082(13) 0.22929(13) 0.5464(13) 0.0865(11) Uani 1 9 b d . .
H9 H 0.01589(13) 0.23076(13) 0.5764(13) 0.104 Uiso 1 9 b calc R .
H10 H 0.08155(13) 0.26853(13) 0.5174(13) 0.104 Uiso 1 9 b calc R .
C6 C 0.06918(14) 0.20587(13) 0.7085(12) 0.0773(10) Uani 1 9 b d . .
H11 H 0.10313(14) 0.23766(13) 0.7664(12) 0.093 Uiso 1 9 b calc R .
H12 H 0.03781(14) 0.18915(13) 0.7968(12) 0.093 Uiso 1 9 b calc R .
C7 C 0.09648(10) 0.19368(11) 0.3272(12) 0.0525(7) Uani 1 9 b d . .
H13 H 0.08868(10) 0.16508(11) 0.2331(12) 0.063 Uiso 1 9 b calc R .
H14 H 0.12268(10) 0.23210(11) 0.2781(12) 0.063 Uiso 1 9 b calc R .
C8 C 0.12505(9) 0.18206(10) 0.4898(12) 0.0412(6) Uani 1 9 b d . .
H15 H 0.13080(9) 0.14948(10) 0.4558(12) 0.049 Uiso 1 9 b calc R .
C9 C 0.18599(10) 0.23387(10) 0.5381(12) 0.0432(7) Uani 1 9 b d . .
H16 H 0.19677(10) 0.22849(10) 0.6607(12) 0.052 Uiso 1 9 b calc R .
C10 C -0.02914(13) 0.0856(2) 0.2994(13) 0.0782(11) Uani 1 9 b d . .
C11 C -0.0504(2) 0.0518(2) 0.1845(13) 0.115(2) Uani 1 9 b d . .
H17 H -0.0676(2) 0.0246(2) 0.0919(13) 0.139 Uiso 1 9 b calc R .
O1' O 0.26605(9) 0.09647(9) 0.7467(12) 0.0799(7) Uani 1 9 b d . .
N1' N 0.30410(9) 0.23044(10) 0.1364(12) 0.0611(7) Uani 1 9 b d . .
C2' C 0.27991(12) 0.26297(12) 0.1215(12) 0.0636(9) Uani 1 9 b d . .
H18 H 0.28791(12) 0.28562(12) 0.0176(12) 0.076 Uiso 1 9 b calc R .
C3' C 0.24286(11) 0.26606(12) 0.2510(12) 0.0549(8) Uani 1 9 b d . .
H19 H 0.22780(11) 0.29074(12) 0.2321(12) 0.066 Uiso 1 9 b calc R .
C4' C 0.22890(10) 0.23353(11) 0.4027(12) 0.0417(7) Uani 1 9 b d . .
C5' C 0.24483(10) 0.16328(11) 0.5846(12) 0.0502(7) Uani 1 9 b d . .
H20 H 0.22006(10) 0.16248(11) 0.6754(12) 0.060 Uiso 1 9 b calc R .
C6' C 0.27206(12) 0.13141(12) 0.6025(12) 0.0607(8) Uani 1 9 b d . .
C7' C 0.30806(13) 0.13120(13) 0.4653(13) 0.0742(11) Uani 1 9 b d . .
H21 H 0.32580(13) 0.10865(13) 0.4778(13) 0.089 Uiso 1 9 b calc R .
C8' C 0.31736(11) 0.16324(13) 0.3152(12) 0.0703(10) Uani 1 9 b d . .
H22 H 0.34147(11) 0.16238(13) 0.2249(12) 0.084 Uiso 1 9 b calc R .
C9' C 0.25429(10) 0.19754(10) 0.4277(12) 0.0434(7) Uani 1 9 b d . .
C10' C 0.29146(11) 0.19832(11) 0.2904(12) 0.0511(8) Uani 1 9 b d . .
C11' C 0.2300(2) 0.09459(13) 0.8922(12) 0.0916(12) Uani 1 9 b d . .
H23 H 0.2293(2) 0.06868(13) 0.9845(12) 0.137 Uiso 1 9 b calc R .
H24 H 0.1911(2) 0.08080(13) 0.8484(12) 0.137 Uiso 1 9 b calc R .
H25 H 0.2452(2) 0.13301(13) 0.9420(12) 0.137 Uiso 1 9 b calc R .
O21 O 0.3199(6) -0.0054(7) 0.2258(16) 0.204(4) Uiso 0.25 9 b d PD .
H201 H 0.3274(8) 0.0165(10) 0.3407(17) 0.305(5) Uiso 0.25 9 b d PD .
C21 C 0.3038(6) 0.0231(6) 0.0923(17) 0.204(4) Uiso 0.25 9 b d PD .
H211 H 0.2701(10) 0.0242(12) 0.1300(25) 0.305(5) Uiso 0.25 9 b d PD .
H212 H 0.3341(11) 0.0624(5) 0.0773(26) 0.305(5) Uiso 0.25 9 b d PD .
C22 C 0.2915(7) -0.0081(7) -0.0900(17) 0.204(4) Uiso 0.25 9 b d PD .
H221 H 0.2808(10) 0.0107(11) -0.1795(20) 0.305(5) Uiso 0.25 9 b d PD .
H222 H 0.2604(10) -0.0472(8) -0.0789(29) 0.305(5) Uiso 0.25 9 b d PD .
H223 H 0.3251(10) -0.0087(13) -0.1315(26) 0.305(5) Uiso 0.25 9 b d PD .
O31 O 0.3330(7) 0.0028(7) 0.6707(15) 0.204(4) Uiso 0.25 9 b d PD .
H301 H 0.3112(8) -0.0351(9) 0.7304(20) 0.305(5) Uiso 0.25 9 b d PD .
C31 C 0.3453(6) -0.0064(5) 0.4886(18) 0.204(4) Uiso 0.25 9 b d PD .
H311 H 0.3099(8) -0.0308(8) 0.4259(19) 0.305(5) Uiso 0.25 9 b d PD .
H312 H 0.3671(11) -0.0260(9) 0.4890(32) 0.305(5) Uiso 0.25 9 b d PD .
C32 C 0.3796(7) 0.0504(7) 0.3802(20) 0.204(4) Uiso 0.25 9 b d PD .
H321 H 0.3873(9) 0.0433(10) 0.2599(21) 0.305(5) Uiso 0.25 9 b d PD .
H322 H 0.3581(11) 0.0703(9) 0.3742(36) 0.305(5) Uiso 0.25 9 b d PD .
H323 H 0.4157(8) 0.0752(8) 0.4388(33) 0.305(5) Uiso 0.25 9 b d PD .
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
C6 N1 C2 108.6(2) . . ?
C6 N1 C8 111.9(2) . . ?
C2 N1 C8 106.0(2) . . ?
C6 N1 B1 110.6(3) . . ?
C2 N1 B1 106.5(2) . . ?
C8 N1 B1 112.9(2) . . ?
N1 C2 C3 111.4(2) . . ?
C10 C3 C2 110.7(3) . . ?
C10 C3 C4 114.2(3) . . ?
C2 C3 C4 107.1(2) . . ?
C5 C4 C7 109.2(2) . . ?
C5 C4 C3 107.4(3) . . ?
C7 C4 C3 109.5(2) . . ?
C4 C5 C6 109.3(2) . . ?
N1 C6 C5 110.3(3) . . ?
C8 C7 C4 109.7(2) . . ?
N1 C8 C7 109.3(2) . . ?
N1 C8 C9 113.2(2) . . ?
C7 C8 C9 113.8(2) . . ?
O1 C9 C4' 110.8(2) . . ?
O1 C9 C8 110.4(2) . . ?
C4' C9 C8 107.2(2) . . ?
C11 C10 C3 178.1(4) . . ?
C6' O1' C11' 117.4(3) . . ?
C2' N1' C10' 115.7(3) . . ?
N1' C2' C3' 124.6(3) . . ?
C4' C3' C2' 120.4(3) . . ?
C3' C4' C9' 117.7(3) . . ?
C3' C4' C9 120.7(2) . . ?
C9' C4' C9 121.6(2) . . ?
C6' C5' C9' 119.9(3) . . ?
C5' C6' O1' 125.2(3) . . ?
C5' C6' C7' 120.5(3) . . ?
O1' C6' C7' 114.3(3) . . ?
C8' C7' C6' 120.5(3) . . ?
C7' C8' C10' 121.7(3) . . ?
C10' C9' C5' 119.9(2) . . ?
C10' C9' C4' 117.2(3) . . ?
C5' C9' C4' 122.9(2) . . ?
N1' C10' C9' 124.3(2) . . ?
N1' C10' C8' 118.1(3) . . ?
C9' C10' C8' 117.6(3) . . ?
O21 C21 C22 111.3(8) . . ?
O31 C31 C32 113.3(8) . . ?
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 C9 1.415(3) . ?
B1 N1 1.622(4) . ?
N1 C6 1.468(3) . ?
N1 C2 1.500(3) . ?
N1 C8 1.517(3) . ?
C2 C3 1.526(4) . ?
C3 C10 1.460(5) . ?
C3 C4 1.536(4) . ?
C4 C5 1.498(4) . ?
C4 C7 1.532(3) . ?
C5 C6 1.534(4) . ?
C7 C8 1.528(4) . ?
C8 C9 1.548(3) . ?
C9 C4' 1.516(3) . ?
C10 C11 1.154(4) . ?
O1' C6' 1.365(4) . ?
O1' C11' 1.420(4) . ?
N1' C2' 1.309(3) . ?
N1' C10' 1.356(4) . ?
C2' C3' 1.400(4) . ?
C3' C4' 1.346(3) . ?
C4' C9' 1.426(3) . ?
C5' C6' 1.362(3) . ?
C5' C9' 1.413(4) . ?
C6' C7' 1.392(4) . ?
C7' C8' 1.340(4) . ?
C8' C10' 1.415(4) . ?
C9' C10' 1.405(3) . ?
O21 C21 1.427(3) . ?
C21 C22 1.525(6) . ?
O31 C31 1.431(3) . ?
C31 C32 1.537(6) . ?
