#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:05:57 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180222 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/08/7110862.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_7110862
loop_
_publ_author_name
'Meth-Cohn, Otto'
'Chen, Yi'
'Williams, David J.'
_publ_section_title
;
 Enantiopure epoxidation of electrophilic alkenes
;
_journal_issue                   6
_journal_name_full               'Chemical Communications'
_journal_page_first              495
_journal_paper_doi               10.1039/b000520g
_journal_year                    2000
_chemical_formula_sum            'C14 H17 N O3'
_chemical_formula_weight         247.29
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 104.16(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.269(2)
_cell_length_b                   8.6418(12)
_cell_length_c                   12.173(2)
_cell_measurement_reflns_used    23
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.45
_cell_measurement_theta_min      5.02
_cell_volume                     639.4(3)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4'
_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  0.0148
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2121
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         2.92
_diffrn_standards_decay_%        6.91
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             264
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.29(161)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.053
_refine_ls_goodness_of_fit_obs   1.076
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1887
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.064
_refine_ls_restrained_S_obs      1.075
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_obs          0.0460
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0781P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1256
_refine_ls_wR_factor_obs         0.1166
_reflns_number_observed          1674
_reflns_number_total             1961
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b000520gsup1.cif
_cod_data_source_block           omc9901
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0781P)^2^+0.0000P] 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^)+(0.0781P)^2^+0.0000P] 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        639.5(2)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7110862
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.6315(3) 0.8049(2) 0.09171(12) 0.0511(4) Uani 1 d .
C2 C 0.4454(3) 0.7459(3) 0.0108(2) 0.0479(4) Uani 1 d .
H2A H 0.3160(3) 0.8066(3) 0.0124(2) 0.057 Uiso 1 calc R
H2B H 0.4185(3) 0.6396(3) 0.0289(2) 0.057 Uiso 1 calc R
C3 C 0.4900(4) 0.7542(2) -0.1048(2) 0.0445(4) Uani 1 d .
H3A H 0.5161(4) 0.8620(2) -0.1230(2) 0.053 Uiso 1 calc R
C4 C 0.3202(5) 0.6820(3) -0.2027(2) 0.0579(5) Uani 1 d .
H4A H 0.2540(5) 0.5908(3) -0.1785(2) 0.070 Uiso 1 calc R
H4B H 0.2053(5) 0.7554(3) -0.2359(2) 0.070 Uiso 1 calc R
C5 C 0.4579(6) 0.6406(4) -0.2850(2) 0.0742(8) Uani 1 d .
H5A H 0.4853(6) 0.7312(4) -0.3265(2) 0.089 Uiso 1 calc R
H5B H 0.3847(6) 0.5628(4) -0.3386(2) 0.089 Uiso 1 calc R
C6 C 0.6723(5) 0.5776(4) -0.2104(2) 0.0628(6) Uani 1 d .
H6A H 0.6644(5) 0.4666(4) -0.2002(2) 0.075 Uiso 1 calc R
H6B H 0.7963(5) 0.6012(4) -0.2420(2) 0.075 Uiso 1 calc R
N7 N 0.6878(3) 0.6613(2) -0.10252(14) 0.0466(4) Uani 1 d .
C8 C 0.8409(3) 0.6320(2) -0.0088(2) 0.0422(4) Uani 1 d .
O8 O 0.9919(3) 0.5374(3) -0.0056(2) 0.0603(4) Uani 1 d .
C9 C 0.8284(3) 0.7199(2) 0.09919(14) 0.0396(3) Uani 1 d .
H9A H 0.9492(3) 0.7949(2) 0.11440(14) 0.048 Uiso 1 calc R
C10 C 0.8702(4) 0.6082(2) 0.2015(2) 0.0467(4) Uani 1 d .
H10A H 0.7593(4) 0.5259(2) 0.1849(2) 0.056 Uiso 1 calc R
O10 O 1.0821(4) 0.5388(3) 0.2191(2) 0.0780(7) Uani 1 d D
H10B H 1.1011(72) 0.5248(64) 0.1489(15) 0.108(16) Uiso 1 d D
C11 C 0.8513(3) 0.6898(2) 0.30882(11) 0.0486(4) Uani 1 d G
C12 C 0.6639(3) 0.6710(3) 0.34927(13) 0.0619(6) Uani 1 d G
H12A H 0.5485(3) 0.6099(3) 0.3096(2) 0.074 Uiso 1 calc R
C13 C 0.6490(3) 0.7435(3) 0.44904(14) 0.0816(10) Uani 1 d G
H13A H 0.5237(4) 0.7310(5) 0.4761(2) 0.098 Uiso 1 calc R
C14 C 0.8216(4) 0.8348(3) 0.50836(13) 0.0861(11) Uani 1 d G
H14A H 0.8116(5) 0.8834(4) 0.5751(2) 0.103 Uiso 1 calc R
C15 C 1.0090(4) 0.8536(3) 0.4679(2) 0.0839(11) Uani 1 d G
H15A H 1.1244(5) 0.9147(4) 0.5076(2) 0.101 Uiso 1 calc R
C16 C 1.0239(3) 0.7811(2) 0.36814(15) 0.0673(7) Uani 1 d G
H16A H 1.1492(3) 0.7937(4) 0.3411(2) 0.081 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'
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
C9 O1 C2 114.30(15)
O1 C2 C3 108.8(2)
N7 C3 C2 107.8(2)
N7 C3 C4 102.5(2)
C2 C3 C4 117.3(2)
C5 C4 C3 102.2(2)
C4 C5 C6 104.6(2)
N7 C6 C5 102.2(2)
C8 N7 C3 123.4(2)
C8 N7 C6 123.2(2)
C3 N7 C6 112.1(2)
O8 C8 N7 122.6(2)
O8 C8 C9 119.7(2)
N7 C8 C9 117.7(2)
O1 C9 C8 115.23(15)
O1 C9 C10 110.4(2)
C8 C9 C10 110.2(2)
O10 C10 C11 109.5(2)
O10 C10 C9 110.6(2)
C11 C10 C9 111.7(2)
C12 C11 C16 120.0
C12 C11 C10 120.17(14)
C16 C11 C10 119.82(14)
C11 C12 C13 120.0
C14 C13 C12 120.0
C15 C14 C13 120.0
C14 C15 C16 120.0
C15 C16 C11 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.420(2)
O1 C2 1.424(3)
C2 C3 1.502(3)
C3 N7 1.472(3)
C3 C4 1.524(3)
C4 C5 1.516(4)
C5 C6 1.526(4)
C6 N7 1.481(3)
N7 C8 1.323(3)
C8 O8 1.244(3)
C8 C9 1.537(2)
C9 C10 1.547(3)
C10 O10 1.425(3)
C10 C11 1.514(2)
C11 C12 1.39
C11 C16 1.39
C12 C13 1.39
C13 C14 1.39
C14 C15 1.39
C15 C16 1.39
