#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/83/1508355.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_1508355
loop_
_publ_author_name
'Chen, Guo-Ying'
'Zhong, Fangrui'
'Lu, Yixin'
_publ_section_title
;
 Asymmetric allylic alkylation of isatin-derived morita-baylis-hillman
 carbonates with nitroalkanes.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3955
_journal_page_last               3957
_journal_paper_doi               10.1021/ol301962e
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H17 Br N2 O5'
_chemical_formula_weight         397.23
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9316(5)
_cell_length_b                   11.5927(7)
_cell_length_c                   19.0616(12)
_cell_measurement_reflns_used    2751
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      22.36
_cell_measurement_theta_min      2.77
_cell_volume                     1752.69(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      223(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0671
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12370
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    2.373
_exptl_absorpt_correction_T_max  0.6483
_exptl_absorpt_correction_T_min  0.3302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.018(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4010
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0296P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0945
_reflns_number_gt                2829
_reflns_number_total             4010
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol301962e_si_002.cif
_cod_data_source_block           b375
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' 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:

'_exptl_crystal_density_meas' value 'not measured' 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 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1508355
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.61352(6) 0.89550(3) 0.37070(2) 0.09039(19) Uani 1 1 d .
O1 O 0.3953(3) 0.27823(18) 0.48723(12) 0.0703(6) Uani 1 1 d .
O2 O 0.2403(3) 0.2914(2) 0.30958(12) 0.0681(7) Uani 1 1 d .
O3 O 0.4560(4) 0.1895(2) 0.3334(2) 0.1156(12) Uani 1 1 d .
O4 O 0.2287(2) 0.5665(2) 0.29659(11) 0.0560(5) Uani 1 1 d .
O5 O -0.0132(2) 0.5722(2) 0.35392(11) 0.0659(6) Uani 1 1 d .
N1 N 0.5220(3) 0.4464(2) 0.52319(13) 0.0564(6) Uani 1 1 d .
N2 N 0.3857(4) 0.2811(2) 0.32877(14) 0.0605(7) Uani 1 1 d .
C1 C 0.5527(3) 0.5555(3) 0.49499(15) 0.0477(7) Uani 1 1 d .
C2 C 0.6390(5) 0.6458(3) 0.52453(18) 0.0681(10) Uani 1 1 d .
H2 H 0.6857 0.6387 0.5691 0.082 Uiso 1 1 calc R
C3 C 0.6555(5) 0.7469(3) 0.48754(19) 0.0699(10) Uani 1 1 d .
H3 H 0.7108 0.8095 0.5076 0.084 Uiso 1 1 calc R
C4 C 0.5908(4) 0.7553(3) 0.42156(17) 0.0554(8) Uani 1 1 d .
C5 C 0.5029(3) 0.6637(2) 0.38993(14) 0.0416(6) Uani 1 1 d .
H5 H 0.4583 0.6704 0.3450 0.050 Uiso 1 1 calc R
C6 C 0.4857(3) 0.5637(2) 0.42824(13) 0.0358(6) Uani 1 1 d .
C7 C 0.3970(3) 0.4502(2) 0.41117(13) 0.0358(5) Uani 1 1 d .
C8 C 0.4354(4) 0.3780(3) 0.47778(16) 0.0488(7) Uani 1 1 d .
C9 C 0.5776(6) 0.4064(4) 0.59227(19) 0.0962(14) Uani 1 1 d .
H9A H 0.5433 0.3277 0.5988 0.144 Uiso 1 1 calc R
H9B H 0.5277 0.4537 0.6280 0.144 Uiso 1 1 calc R
H9C H 0.6982 0.4115 0.5952 0.144 Uiso 1 1 calc R
C10 C 0.4799(3) 0.3917(2) 0.34618(15) 0.0462(6) Uani 1 1 d .
H10 H 0.4670 0.4442 0.3063 0.055 Uiso 1 1 calc R
C11 C 0.6671(4) 0.3680(3) 0.35527(19) 0.0646(9) Uani 1 1 d .
H11A H 0.7198 0.4354 0.3759 0.077 Uiso 1 1 calc R
H11B H 0.6811 0.3044 0.3879 0.077 Uiso 1 1 calc R
C12 C 0.7572(4) 0.3390(4) 0.2881(3) 0.1042(18) Uani 1 1 d .
H12A H 0.7132 0.2681 0.2695 0.156 Uiso 1 1 calc R
H12B H 0.8755 0.3304 0.2972 0.156 Uiso 1 1 calc R
H12C H 0.7402 0.3999 0.2547 0.156 Uiso 1 1 calc R
C13 C 0.2066(3) 0.4702(2) 0.40735(14) 0.0359(6) Uani 1 1 d .
C14 C 0.0999(4) 0.4365(3) 0.45632(14) 0.0467(6) Uani 1 1 d .
H14A H -0.0135 0.4563 0.4531 0.056 Uiso 1 1 calc R
H14B H 0.1380 0.3929 0.4941 0.056 Uiso 1 1 calc R
C15 C 0.1458(3) 0.5402(2) 0.34654(13) 0.0365(6) Uani 1 1 d .
C16 C -0.0836(4) 0.6416(4) 0.2979(2) 0.0838(13) Uani 1 1 d .
H16A H -0.0443 0.7196 0.3024 0.126 Uiso 1 1 calc R
H16B H -0.2044 0.6403 0.3009 0.126 Uiso 1 1 calc R
H16C H -0.0488 0.6109 0.2535 0.126 Uiso 1 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'
Br Br -0.2901 2.4595 '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
C15 O5 C16 116.4(2)
C8 N1 C1 111.8(2)
C8 N1 C9 122.6(3)
C1 N1 C9 125.5(3)
O3 N2 O2 123.3(3)
O3 N2 C10 120.0(3)
O2 N2 C10 116.7(3)
C2 C1 C6 121.2(3)
C2 C1 N1 128.3(3)
C6 C1 N1 110.5(2)
C1 C2 C3 119.2(3)
C4 C3 C2 119.9(3)
C3 C4 C5 121.9(3)
C3 C4 Br1 119.8(2)
C5 C4 Br1 118.3(2)
C6 C5 C4 117.2(2)
C5 C6 C1 120.5(2)
C5 C6 C7 131.2(2)
C1 C6 C7 108.3(2)
C6 C7 C13 109.6(2)
C6 C7 C8 101.5(2)
C13 C7 C8 108.3(2)
C6 C7 C10 110.5(2)
C13 C7 C10 116.4(2)
C8 C7 C10 109.5(2)
O1 C8 N1 126.4(3)
O1 C8 C7 125.8(3)
N1 C8 C7 107.8(2)
C11 C10 N2 110.6(3)
C11 C10 C7 113.6(2)
N2 C10 C7 109.5(2)
C12 C11 C10 114.0(3)
C14 C13 C15 120.2(2)
C14 C13 C7 123.7(2)
C15 C13 C7 115.9(2)
O4 C15 O5 122.5(2)
O4 C15 C13 125.3(2)
O5 C15 C13 112.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C4 1.901(3)
O1 C8 1.213(3)
O2 N2 1.216(4)
O3 N2 1.203(4)
O4 C15 1.197(3)
O5 C15 1.322(3)
O5 C16 1.448(4)
N1 C8 1.360(4)
N1 C1 1.396(4)
N1 C9 1.464(4)
N2 C10 1.521(4)
C1 C2 1.371(4)
C1 C6 1.382(4)
C2 C3 1.374(5)
C3 C4 1.362(5)
C4 C5 1.406(4)
C5 C6 1.377(4)
C6 C7 1.527(3)
C7 C13 1.530(4)
C7 C8 1.551(4)
C7 C10 1.558(4)
C10 C11 1.520(4)
C11 C12 1.504(5)
C13 C14 1.319(4)
C13 C15 1.495(4)
