#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/12/7151233.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_7151233
loop_
_publ_author_name
'Davies, Stephen G.'
'Garner, A. Christopher'
'Roberts, Paul M.'
'Smith, Andrew D.'
'Sweet, Miles J.'
'Thomson, James E.'
_publ_section_title
;
 Oxazinanones as chiral auxiliaries: synthesis and evaluation in
 enolate alkylations and aldol reactions.
;
_journal_issue                   14
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2753
_journal_page_last               2768
_journal_paper_doi               10.1039/b604073j
_journal_volume                  4
_journal_year                    2006
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C19 H27 N1 O4'
_chemical_formula_sum            'C19 H27 N O4'
_chemical_formula_weight         333.43
_chemical_melting_point          ?
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 119.6642(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.9151(5)
_cell_length_b                   9.5994(3)
_cell_length_c                   12.1722(4)
_cell_measurement_reflns_used    2024
_cell_measurement_temperature    190
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1818.96(10)
_computing_cell_refinement
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_computing_data_collection
;
COLLECT (Nonius BV, 1997)
;
_computing_data_reduction
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_computing_molecular_graphics
;
CAMERON (Watkin et al 1996)
;
_computing_publication_material
;
CRYSTALS (Watkin et al 2001)
;
_computing_structure_refinement
;
CRYSTALS (Watkin et al 2001)
;
_computing_structure_solution
;
SIR92 (Altomare et al, 1994)
;
_diffrn_ambient_temperature      190
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type
;
Enraf Nonius Kappa CCD
;
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.01
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3934
_diffrn_reflns_theta_full        26.511
_diffrn_reflns_theta_max         27.472
_diffrn_reflns_theta_min         5.107
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_crystal_colour            ' colourless '
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_meas      ?
_exptl_crystal_description       ' block '
_exptl_crystal_F_000             720.000
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.13
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1371
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         1765
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.000389
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method = Prince modified Chebychev polynomial, (Watkin, 1994)
W = [weight] * [1-(deltaF/6*sigmaF)^2]^2

0.599 0.224 0.274 0.558E-01
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0465
_refine_ls_wR_factor_gt          0.0365
_refine_ls_wR_factor_ref         0.0365
_reflns_limit_h_max              20
_reflns_limit_h_min              -22
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                1765
_reflns_number_total             2192
_reflns_threshold_expression     I>3.00u(I)
_cod_data_source_file            b604073j.txt
_cod_data_source_block           CRYSTALS_cif
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_cell_volume        1819.0(1)
_cod_original_sg_symbol_H-M      'C 2'
_cod_original_formula_sum        'C19 H27 N1 O4'
_cod_database_code               7151233
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,y+1/2,z
-x,y,-z
-x+1/2,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_occupancy
_atom_site_adp_type
_atom_site_attached_hydrogens
N1 N 0.9100(1) 0.22712(19) 0.20239(15) 0.0283 1.0000 Uani .
C2 C 0.82720(11) 0.3044(2) 0.16086(18) 0.0288 1.0000 Uani .
C3 C 0.82475(12) 0.4349(2) 0.08828(18) 0.0306 1.0000 Uani .
C4 C 0.87441(11) 0.4168(2) 0.01792(18) 0.0297 1.0000 Uani .
O5 O 0.96408(8) 0.38944(16) 0.11710(13) 0.0321 1.0000 Uani .
C6 C 0.98168(11) 0.2948(2) 0.20682(18) 0.0286 1.0000 Uani .
O7 O 1.05499(8) 0.26962(18) 0.28312(15) 0.0395 1.0000 Uani .
C8 C 0.84283(13) 0.2990(3) -0.07766(19) 0.0388 1.0000 Uani .
C9 C 0.87977(14) 0.5523(3) -0.0417(2) 0.0387 1.0000 Uani .
C10 C 0.81482(14) 0.3339(3) 0.2754(2) 0.0385 1.0000 Uani .
C11 C 0.72781(14) 0.4025(3) 0.2320(2) 0.0414 1.0000 Uani .
C12 C 0.88683(16) 0.4231(5) 0.3766(2) 0.0701 1.0000 Uani .
C13 C 0.91114(12) 0.0868(2) 0.23032(19) 0.0291 1.0000 Uani .
C14 C 0.98907(11) -0.0027(2) 0.26157(18) 0.0278 1.0000 Uani .
C15 C 0.98444(12) -0.1396(2) 0.32426(19) 0.0310 1.0000 Uani .
C16 C 1.06871(12) -0.2178(2) 0.37967(18) 0.0291 1.0000 Uani .
C17 C 1.07852(14) -0.3353(2) 0.3224(2) 0.0381 1.0000 Uani .
C18 C 1.15727(16) -0.4022(3) 0.3729(2) 0.0444 1.0000 Uani .
C19 C 1.22735(14) -0.3522(3) 0.4821(2) 0.0431 1.0000 Uani .
C20 C 1.21798(13) -0.2352(3) 0.5414(2) 0.0384 1.0000 Uani .
C21 C 1.13892(13) -0.1684(2) 0.4905(2) 0.0333 1.0000 Uani .
H21 H 0.7778 0.2445 0.0999 0.0371 1.0000 Uiso .
O22 O 0.91670(9) -0.22767(19) 0.23644(17) 0.0466 1.0000 Uani .
C23 C 0.99367(16) -0.0283(3) 0.1402(2) 0.0425 1.0000 Uani .
O24 O 0.84584(9) 0.03440(17) 0.22145(16) 0.0400 1.0000 Uani .
H31 H 0.8502 0.5140 0.1505 0.0408 1.0000 Uiso .
H32 H 0.7633 0.4579 0.0266 0.0408 1.0000 Uiso .
H81 H 0.8781 0.2936 -0.1206 0.0496 1.0000 Uiso .
H82 H 0.8462 0.2086 -0.0351 0.0496 1.0000 Uiso .
H83 H 0.7810 0.3167 -0.1440 0.0496 1.0000 Uiso .
H91 H 0.9126 0.5381 -0.0882 0.0497 1.0000 Uiso .
H92 H 0.9090 0.6259 0.0240 0.0497 1.0000 Uiso .
H93 H 0.8201 0.5855 -0.1045 0.0497 1.0000 Uiso .
H101 H 0.8169 0.2394 0.3170 0.0517 1.0000 Uiso .
H111 H 0.7185 0.4229 0.3046 0.0558 1.0000 Uiso .
H112 H 0.7261 0.4948 0.1890 0.0558 1.0000 Uiso .
H113 H 0.6797 0.3433 0.1687 0.0558 1.0000 Uiso .
H121 H 0.8770 0.4381 0.4496 0.0820 1.0000 Uiso .
H122 H 0.9439 0.3753 0.4076 0.0820 1.0000 Uiso .
H123 H 0.8880 0.5147 0.3386 0.0820 1.0000 Uiso .
H141 H 1.0437 0.0479 0.3234 0.0366 1.0000 Uiso .
H151 H 0.9724 -0.1160 0.3951 0.0395 1.0000 Uiso .
H171 H 1.0271 -0.3728 0.2436 0.0442 1.0000 Uiso .
H181 H 1.1639 -0.4882 0.3298 0.0551 1.0000 Uiso .
H191 H 1.2852 -0.3987 0.5187 0.0493 1.0000 Uiso .
H201 H 1.2679 -0.1987 0.6207 0.0469 1.0000 Uiso .
H211 H 1.1325 -0.0846 0.5346 0.0400 1.0000 Uiso .
H221 H 0.8667 -0.1700 0.2212 0.0500 1.0000 Uiso .
H231 H 1.0446 -0.0875 0.1583 0.0593 1.0000 Uiso .
H232 H 0.9970 0.0614 0.1011 0.0593 1.0000 Uiso .
H233 H 0.9399 -0.0797 0.0764 0.0593 1.0000 Uiso .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 International_Tables_Vol_IV_Table_2.2B
'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 International_Tables_Vol_IV_Table_2.2B
'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 International_Tables_Vol_IV_Table_2.2B
'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 International_Tables_Vol_IV_Table_2.2B
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C6 . 120.77(16) yes
C2 . N1 . C13 . 116.92(16) yes
C6 . N1 . C13 . 122.25(16) yes
N1 . C2 . C3 . 109.93(15) yes
N1 . C2 . C10 . 110.24(15) yes
C3 . C2 . C10 . 113.45(18) yes
N1 . C2 . H21 . 109.159 no
C3 . C2 . H21 . 106.259 no
C10 . C2 . H21 . 107.625 no
C2 . C3 . C4 . 112.12(17) yes
C2 . C3 . H31 . 108.171 no
C4 . C3 . H31 . 109.638 no
C2 . C3 . H32 . 108.753 no
C4 . C3 . H32 . 109.585 no
H31 . C3 . H32 . 108.495 no
C3 . C4 . O5 . 105.23(14) yes
C3 . C4 . C8 . 114.67(17) yes
O5 . C4 . C8 . 109.64(17) yes
C3 . C4 . C9 . 111.43(18) yes
O5 . C4 . C9 . 104.03(16) yes
C8 . C4 . C9 . 111.11(17) yes
C4 . O5 . C6 . 120.70(15) yes
N1 . C6 . O5 . 116.05(15) yes
N1 . C6 . O7 . 124.19(19) yes
O5 . C6 . O7 . 119.73(17) yes
C4 . C8 . H81 . 110.300 no
C4 . C8 . H82 . 110.304 no
H81 . C8 . H82 . 109.570 no
C4 . C8 . H83 . 109.435 no
H81 . C8 . H83 . 108.435 no
H82 . C8 . H83 . 108.756 no
C4 . C9 . H91 . 110.287 no
C4 . C9 . H92 . 110.833 no
H91 . C9 . H92 . 109.018 no
C4 . C9 . H93 . 109.833 no
H91 . C9 . H93 . 108.119 no
H92 . C9 . H93 . 108.689 no
C2 . C10 . C11 . 110.22(16) yes
C2 . C10 . C12 . 112.92(19) yes
C11 . C10 . C12 . 110.3(2) yes
C2 . C10 . H101 . 107.216 no
C11 . C10 . H101 . 109.394 no
C12 . C10 . H101 . 106.637 no
C10 . C11 . H111 . 111.599 no
C10 . C11 . H112 . 108.522 no
H111 . C11 . H112 . 107.940 no
C10 . C11 . H113 . 111.375 no
H111 . C11 . H113 . 109.656 no
H112 . C11 . H113 . 107.598 no
C10 . C12 . H121 . 110.358 no
C10 . C12 . H122 . 109.927 no
H121 . C12 . H122 . 108.983 no
C10 . C12 . H123 . 108.793 no
H121 . C12 . H123 . 109.811 no
H122 . C12 . H123 . 108.949 no
N1 . C13 . C14 . 120.68(17) yes
N1 . C13 . O24 . 118.60(18) yes
C14 . C13 . O24 . 120.56(19) yes
C13 . C14 . C15 . 109.74(16) yes
C13 . C14 . C23 . 109.23(16) yes
C15 . C14 . C23 . 112.33(18) yes
C13 . C14 . H141 . 110.219 no
C15 . C14 . H141 . 107.987 no
C23 . C14 . H141 . 107.300 no
C14 . C15 . C16 . 110.91(16) yes
C14 . C15 . O22 . 111.56(16) yes
C16 . C15 . O22 . 109.30(18) yes
C14 . C15 . H151 . 108.439 no
C16 . C15 . H151 . 108.490 no
O22 . C15 . H151 . 108.044 no
C15 . C16 . C17 . 121.85(18) yes
C15 . C16 . C21 . 119.06(19) yes
C17 . C16 . C21 . 119.08(19) yes
C16 . C17 . C18 . 120.7(2) yes
C16 . C17 . H171 . 119.027 no
C18 . C17 . H171 . 120.298 no
C17 . C18 . C19 . 120.3(2) yes
C17 . C18 . H181 . 120.051 no
C19 . C18 . H181 . 119.672 no
C18 . C19 . C20 . 119.6(2) yes
C18 . C19 . H191 . 121.016 no
C20 . C19 . H191 . 119.420 no
C19 . C20 . C21 . 120.0(2) yes
C19 . C20 . H201 . 120.289 no
C21 . C20 . H201 . 119.692 no
C16 . C21 . C20 . 120.4(2) yes
C16 . C21 . H211 . 120.127 no
C20 . C21 . H211 . 119.486 no
C15 . O22 . H221 . 99.437 no
C14 . C23 . H231 . 110.796 no
C14 . C23 . H232 . 111.293 no
H231 . C23 . H232 . 109.258 no
C14 . C23 . H233 . 109.303 no
H231 . C23 . H233 . 107.938 no
H232 . C23 . H233 . 108.156 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.505(2) yes
N1 . C6 . 1.415(2) yes
N1 . C13 . 1.387(3) yes
C2 . C3 . 1.521(3) yes
C2 . C10 . 1.542(3) yes
C2 . H21 . 1.007 no
C3 . C4 . 1.520(3) yes
C3 . H31 . 1.008 no
C3 . H32 . 1.004 no
C4 . O5 . 1.479(2) yes
C4 . C8 . 1.516(3) yes
C4 . C9 . 1.516(3) yes
O5 . C6 . 1.333(2) yes
C6 . O7 . 1.199(2) yes
C8 . H81 . 1.001 no
C8 . H82 . 0.997 no
C8 . H83 . 1.012 no
C9 . H91 . 1.006 no
C9 . H92 . 0.999 no
C9 . H93 . 1.011 no
C10 . C11 . 1.525(3) yes
C10 . C12 . 1.531(4) yes
C10 . H101 . 1.030 no
C11 . H111 . 0.997 no
C11 . H112 . 1.023 no
C11 . H113 . 1.001 no
C12 . H121 . 0.998 no
C12 . H122 . 1.008 no
C12 . H123 . 0.998 no
C13 . C14 . 1.518(3) yes
C13 . O24 . 1.228(2) yes
C14 . C15 . 1.543(3) yes
C14 . C23 . 1.540(3) yes
C14 . H141 . 1.015 no
C15 . C16 . 1.513(3) yes
C15 . O22 . 1.430(3) yes
C15 . H151 . 1.012 no
C16 . C17 . 1.382(3) yes
C16 . C21 . 1.395(3) yes
C17 . C18 . 1.387(3) yes
C17 . H171 . 1.012 no
C18 . C19 . 1.387(4) yes
C18 . H181 . 1.015 no
C19 . C20 . 1.388(4) yes
C19 . H191 . 1.008 no
C20 . C21 . 1.390(3) yes
C20 . H201 . 1.000 no
C21 . H211 . 1.004 no
O22 . H221 . 0.990 no
C23 . H231 . 1.003 no
C23 . H232 . 1.000 no
C23 . H233 . 1.017 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9884478
