#------------------------------------------------------------------------------
#$Date: 2025-08-20 16:59:05 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301833 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/67/4116746.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_4116746
loop_
_publ_author_name
'Jurriaan Huskens'
'Richard Goddard'
'Manfred T. Reetz'
_publ_section_title
;
 Direct Observation of Stereotopic Group Recognition in Solution and Solid
 State
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6617
_journal_page_last               6618
_journal_paper_doi               10.1021/ja980215x
_journal_volume                  120
_journal_year                    1998
_chemical_formula_moiety         'C21 H29 B N2 O3'
_chemical_formula_sum            'C21 H29 B N2 O3'
_chemical_formula_weight         368.27
_chemical_name_systematic
; 
 2-(1,3-bis(dimethylamino)propan-2-oxy-N,O)-4,5-diphenyl-1,3,2-dioxaborolane 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 95.762(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.6052(8)
_cell_length_b                   9.7625(8)
_cell_length_c                   10.2093(12)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      20.50
_cell_measurement_theta_min      19.25
_cell_volume                     1051.66(17)
_computing_cell_refinement       'EXPRESS / CAD4 software (Enraf-Nonius, 1995)'
_computing_data_collection       'EXPRESS / CAD4 software (Enraf-Nonius, 1995)'
_computing_data_reduction
'DATAP (Coppens,Leiserowitz & Rabinovich, 1965)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       'ω-2θ scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_sigmaI/netI    0.0674
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5037
_diffrn_reflns_theta_full        27.41
_diffrn_reflns_theta_max         27.41
_diffrn_reflns_theta_min         2.64
_diffrn_standards_decay_%        2.91
_diffrn_standards_interval_time  30
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       prism
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack, H. D. (1983). Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.9(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4787
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_obs          0.0449
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0517P)²+0.1210P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.1132
_refine_ls_wR_factor_ref         0.1341
_reflns_number_observed          3510
_reflns_number_total             4787
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja980215x.cif
_cod_data_source_block           2660
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' 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^)+(0.0517P)^2^+0.1210P] where 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^)+(0.0517P)^2^+0.1210P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1051.66(16)
_cod_database_code               4116746
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_calc_flag
_atom_site_refinement_flags
O1 O 0.68787(13) 0.33426(14) -0.00403(14) 0.0468(3) Uani 1 d .
O2 O 0.82045(13) 0.47687(15) -0.11111(16) 0.0506(4) Uani 1 d .
O3 O 0.87973(14) 0.43127(15) 0.11693(17) 0.0549(4) Uani 1 d .
N1 N 0.90519(17) 0.24245(17) -0.02334(19) 0.0478(4) Uani 1 d .
N2 N 0.8762(3) 0.1919(3) 0.3949(2) 0.0792(7) Uani 1 d .
B B 0.8168(2) 0.3815(2) -0.0055(3) 0.0463(5) Uani 1 d .
C1 C 0.61009(18) 0.4237(2) -0.0865(2) 0.0419(4) Uani 1 d .
H1 H 0.5861 0.5016 -0.0338 0.050 Uiso 1 calc R
C2 C 0.69903(18) 0.4755(2) -0.1866(2) 0.0441(5) Uani 1 d .
H2 H 0.7002 0.4086 -0.2580 0.053 Uiso 1 calc R
C3 C 0.49158(18) 0.3557(2) -0.1477(2) 0.0430(5) Uani 1 d .
C4 C 0.4818(2) 0.2144(2) -0.1578(2) 0.0528(5) Uani 1 d .
H4 H 0.5500 0.1598 -0.1263 0.063 Uiso 1 calc R
C5 C 0.3713(2) 0.1536(3) -0.2145(3) 0.0623(7) Uani 1 d .
H5 H 0.3656 0.0587 -0.2195 0.075 Uiso 1 calc R
C6 C 0.2708(2) 0.2324(3) -0.2629(3) 0.0613(6) Uani 1 d .
H6 H 0.1972 0.1913 -0.3016 0.074 Uiso 1 calc R
C7 C 0.2792(2) 0.3729(3) -0.2541(3) 0.0666(7) Uani 1 d .
H7 H 0.2112 0.4269 -0.2876 0.080 Uiso 1 calc R
C8 C 0.3882(2) 0.4336(3) -0.1957(3) 0.0571(6) Uani 1 d .
H8 H 0.3922 0.5285 -0.1885 0.068 Uiso 1 calc R
C9 C 0.66448(19) 0.6137(2) -0.2443(2) 0.0467(5) Uani 1 d .
C10 C 0.6599(3) 0.7264(2) -0.1634(3) 0.0634(7) Uani 1 d .
H10 H 0.6839 0.7177 -0.0737 0.076 Uiso 1 calc R
C11 C 0.6201(3) 0.8526(3) -0.2146(4) 0.0805(9) Uani 1 d .
H11 H 0.6157 0.9274 -0.1587 0.097 Uiso 1 calc R
C12 C 0.5876(3) 0.8674(3) -0.3454(4) 0.0891(10) Uani 1 d .
H12 H 0.5631 0.9528 -0.3794 0.107 Uiso 1 calc R
C13 C 0.5909(3) 0.7563(4) -0.4287(3) 0.0933(12) Uani 1 d .
H13 H 0.5677 0.7666 -0.5185 0.112 Uiso 1 calc R
C14 C 0.6287(3) 0.6293(3) -0.3782(3) 0.0679(7) Uani 1 d .
H14 H 0.6301 0.5542 -0.4342 0.081 Uiso 1 calc R
C15 C 0.9192(2) 0.1923(2) 0.1144(3) 0.0550(6) Uani 1 d .
H15A H 0.9959 0.1384 0.1318 0.066 Uiso 1 calc R
H15B H 0.8471 0.1366 0.1321 0.066 Uiso 1 calc R
C16 C 0.9262(2) 0.3226(2) 0.1987(2) 0.0568(6) Uani 1 d .
H16 H 1.0145 0.3407 0.2321 0.068 Uiso 1 calc R
C17 C 0.8457(3) 0.3103(3) 0.3136(3) 0.0697(7) Uani 1 d .
H17A H 0.8572 0.3920 0.3676 0.084 Uiso 1 calc R
H17B H 0.7571 0.3057 0.2794 0.084 Uiso 1 calc R
C18 C 0.8470(3) 0.1387(3) -0.1154(3) 0.0677(7) Uani 1 d .
H18A H 0.8395 0.1749 -0.2032 0.101 Uiso 1 calc R
H18B H 0.7644 0.1155 -0.0913 0.101 Uiso 1 calc R
H18C H 0.8992 0.0582 -0.1114 0.101 Uiso 1 calc R
C19 C 1.0301(2) 0.2820(3) -0.0658(3) 0.0662(7) Uani 1 d .
H19A H 1.0690 0.3496 -0.0066 0.099 Uiso 1 calc R
H19B H 1.0184 0.3192 -0.1533 0.099 Uiso 1 calc R
H19C H 1.0838 0.2027 -0.0652 0.099 Uiso 1 calc R
C20 C 1.0007(6) 0.2034(6) 0.4686(6) 0.164(3) Uani 1 d .
H20A H 1.0174 0.1228 0.5214 0.247 Uiso 1 calc R
H20B H 1.0026 0.2825 0.5246 0.247 Uiso 1 calc R
H20C H 1.0641 0.2125 0.4083 0.247 Uiso 1 calc R
C21 C 0.7793(5) 0.1675(5) 0.4851(4) 0.1298(18) Uani 1 d .
H21A H 0.8018 0.0883 0.5380 0.195 Uiso 1 calc R
H21B H 0.6988 0.1525 0.4352 0.195 Uiso 1 calc R
H21C H 0.7737 0.2458 0.5411 0.195 Uiso 1 calc 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_publ_flag
C1 O1 B 106.99(15) y
B O2 C2 108.00(16) y
C16 O3 B 111.35(17) y
C18 N1 C15 111.93(19) y
C18 N1 C19 108.7(2) y
C15 N1 C19 110.8(2) y
C18 N1 B 115.11(18) y
C15 N1 B 99.72(17) y
C19 N1 B 110.32(17) y
C17 N2 C20 112.0(3) y
C17 N2 C21 111.2(3) y
C20 N2 C21 110.2(4) y
O2 B O3 112.94(18) y
O2 B O1 108.25(18) y
O3 B O1 117.1(2) y
O2 B N1 112.90(19) y
O3 B N1 98.78(17) y
O1 B N1 106.49(16) y
O1 C1 C3 112.81(16) y
O1 C1 C2 103.72(15) y
C3 C1 C2 114.27(17) y
O2 C2 C9 111.91(17) y
O2 C2 C1 102.87(16) y
C9 C2 C1 114.38(17) y
C8 C3 C4 118.1(2) y
C8 C3 C1 120.32(19) y
C4 C3 C1 121.63(19) y
C5 C4 C3 120.7(2) y
C6 C5 C4 120.4(2) y
C5 C6 C7 119.6(2) y
C6 C7 C8 120.1(2) y
C7 C8 C3 121.1(2) y
C10 C9 C14 118.6(2) y
C10 C9 C2 120.2(2) y
C14 C9 C2 121.0(2) y
C9 C10 C11 120.7(3) y
C12 C11 C10 120.2(3) y
C11 C12 C13 120.3(3) y
C12 C13 C14 119.8(3) y
C13 C14 C9 120.2(3) y
N1 C15 C16 104.66(17) y
O3 C16 C17 109.0(2) y
O3 C16 C15 107.35(18) y
C17 C16 C15 111.6(2) y
N2 C17 C16 113.3(2) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.418(2) y
O1 B 1.444(3) y
O2 B 1.428(3) y
O2 C2 1.433(2) y
O3 C16 1.408(3) y
O3 B 1.441(3) y
N1 C18 1.474(3) y
N1 C15 1.482(3) y
N1 C19 1.486(3) y
N1 B 1.670(3) y
N2 C17 1.441(4) y
N2 C20 1.456(6) y
N2 C21 1.466(5) y
C1 C3 1.501(3) y
C1 C2 1.544(3) y
C2 C9 1.502(3) y
C3 C8 1.384(3) y
C3 C4 1.386(3) y
C4 C5 1.386(3) y
C5 C6 1.366(4) y
C6 C7 1.377(4) y
C7 C8 1.381(3) y
C9 C10 1.380(3) y
C9 C14 1.390(3) y
C10 C11 1.387(4) y
C11 C12 1.354(5) y
C12 C13 1.381(5) y
C13 C14 1.387(4) y
C15 C16 1.533(3) y
C16 C17 1.524(4) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139120620
