#------------------------------------------------------------------------------
#$Date: 2018-01-06 04:15:18 +0200 (Sat, 06 Jan 2018) $
#$Revision: 204840 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/30/4033097.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_4033097
loop_
_publ_author_name
'Hsieh, Yu-You'
'Raja, Arun'
'Hong, Bor-Cherng'
'Kotame, Prakash'
'Chang, Wan-Chen'
'Lee, Gene-Hsiang'
_publ_section_title
;
 Organocatalytic Enantioselective Michael-Acetalization-Henry Reaction
 Cascade of 2-Hydroxynitrostyrene and 5-Oxohexanal for the Entry to the
 Hexahydro-6H-benzo[c]chromenones with Four Consecutive Stereogenic
 Centers and an Approach to Aflatoxin Analogues.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12840
_journal_page_last               12848
_journal_paper_doi               10.1021/acs.joc.7b02178
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H14 Br N O5'
_chemical_formula_weight         356.17
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.7253(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.9789(7)
_cell_length_b                   7.0934(5)
_cell_length_c                   11.0379(7)
_cell_measurement_reflns_used    3655
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.90
_cell_measurement_theta_min      2.27
_cell_volume                     703.87(8)
_computing_cell_refinement       'Bruker SAINT'
_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      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'BRUKER SMART APEXCCD area detector'
_diffrn_measurement_method       '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  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11543
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    2.941
_exptl_absorpt_correction_T_max  0.8433
_exptl_absorpt_correction_T_min  0.3210
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.986
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.018(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3219
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0567P)²+0.4283P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                3012
_reflns_number_total             3219
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02178_si_002.cif
_cod_data_source_block           ic15687_compound_4b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4033097--4033099.cif.
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4033097
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.09947(4) 0.24638(6) 1.23648(3) 0.03162(12) Uani 1 1 d .
O1 O -0.0681(2) 0.2564(6) 0.6434(2) 0.0206(5) Uani 1 1 d .
O2 O -0.0239(3) 0.3312(4) 0.4723(3) 0.0277(6) Uani 1 1 d .
O3 O 0.5347(3) 0.1619(4) 0.8145(3) 0.0249(6) Uani 1 1 d .
H3 H 0.5229 0.2674 0.8431 0.037 Uiso 1 1 calc R
O4 O 0.3100(3) -0.2181(3) 0.8765(3) 0.0279(6) Uani 1 1 d .
O5 O 0.4202(3) 0.0153(4) 1.0082(2) 0.0277(6) Uani 1 1 d .
N1 N 0.3407(3) -0.0504(5) 0.8968(3) 0.0198(6) Uani 1 1 d .
C1 C 0.0237(4) 0.3271(5) 0.5917(4) 0.0194(7) Uani 1 1 d .
C2 C 0.1751(4) 0.3971(5) 0.6916(3) 0.0182(7) Uani 1 1 d .
H2 H 0.1609 0.5258 0.7211 0.022 Uiso 1 1 calc R
C3 C 0.2816(4) 0.4163(5) 0.6264(4) 0.0227(7) Uani 1 1 d .
H3A H 0.3715 0.4859 0.6878 0.027 Uiso 1 1 calc R
H3B H 0.2329 0.4899 0.5422 0.027 Uiso 1 1 calc R
C4 C 0.3271(4) 0.2235(6) 0.5950(3) 0.0215(8) Uani 1 1 d .
H4A H 0.3999 0.2417 0.5573 0.026 Uiso 1 1 calc R
H4B H 0.2384 0.1610 0.5254 0.026 Uiso 1 1 calc R
C5 C 0.3955(4) 0.0942(5) 0.7178(3) 0.0178(7) Uani 1 1 d .
C6 C 0.2799(3) 0.0798(4) 0.7771(3) 0.0143(6) Uani 1 1 d .
H6 H 0.1870 0.0222 0.7072 0.017 Uiso 1 1 calc R
C7 C 0.2396(3) 0.2726(6) 0.8164(3) 0.0148(7) Uani 1 1 d .
H7 H 0.3317 0.3329 0.8853 0.018 Uiso 1 1 calc R
C8 C 0.1265(3) 0.2547(7) 0.8724(3) 0.0162(5) Uani 1 1 d .
C9 C -0.0228(3) 0.2493(7) 0.7822(3) 0.0183(5) Uani 1 1 d .
C10 C -0.1353(3) 0.2351(7) 0.8231(3) 0.0221(6) Uani 1 1 d .
H10 H -0.2364 0.2293 0.7588 0.027 Uiso 1 1 calc R
C11 C -0.0977(4) 0.2294(7) 0.9602(3) 0.0225(7) Uani 1 1 d .
H11 H -0.1727 0.2173 0.9909 0.027 Uiso 1 1 calc R
C12 C 0.0501(4) 0.2416(7) 1.0504(3) 0.0215(6) Uani 1 1 d .
C13 C 0.1617(3) 0.2539(7) 1.0093(3) 0.0200(6) Uani 1 1 d .
H13 H 0.2626 0.2617 1.0740 0.024 Uiso 1 1 calc R
C14 C 0.4284(4) -0.0975(5) 0.6752(4) 0.0245(8) Uani 1 1 d .
H14A H 0.4929 -0.0815 0.6297 0.037 Uiso 1 1 calc R
H14B H 0.3350 -0.1573 0.6136 0.037 Uiso 1 1 calc R
H14C H 0.4785 -0.1773 0.7548 0.037 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
C1 O1 C9 120.9(3)
O4 N1 O5 123.6(3)
O4 N1 C6 117.5(3)
O5 N1 C6 118.9(3)
O2 C1 O1 116.9(3)
O2 C1 C2 126.1(3)
O1 C1 C2 117.0(3)
C1 C2 C7 111.3(3)
C1 C2 C3 111.4(3)
C7 C2 C3 111.8(3)
C2 C3 C4 111.3(3)
C3 C4 C5 113.4(3)
O3 C5 C14 105.3(3)
O3 C5 C4 112.2(3)
C14 C5 C4 109.6(3)
O3 C5 C6 111.6(3)
C14 C5 C6 111.7(3)
C4 C5 C6 106.5(3)
N1 C6 C7 110.6(3)
N1 C6 C5 108.6(3)
C7 C6 C5 113.1(3)
C8 C7 C2 108.8(3)
C8 C7 C6 112.0(3)
C2 C7 C6 108.6(3)
C9 C8 C13 117.7(3)
C9 C8 C7 118.0(2)
C13 C8 C7 124.3(3)
C10 C9 C8 122.6(3)
C10 C9 O1 116.0(2)
C8 C9 O1 121.5(2)
C9 C10 C11 118.9(3)
C12 C11 C10 118.9(3)
C13 C12 C11 122.1(3)
C13 C12 Br1 119.3(2)
C11 C12 Br1 118.6(2)
C12 C13 C8 119.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C12 1.893(3)
O1 C1 1.368(4)
O1 C9 1.397(3)
O2 C1 1.192(4)
O3 C5 1.418(4)
O4 N1 1.224(4)
O5 N1 1.230(4)
N1 C6 1.507(4)
C1 C2 1.516(5)
C2 C7 1.524(5)
C2 C3 1.526(5)
C3 C4 1.528(6)
C4 C5 1.531(5)
C5 C14 1.521(5)
C5 C6 1.557(5)
C6 C7 1.540(5)
C7 C8 1.509(4)
C8 C9 1.387(4)
C8 C13 1.395(4)
C9 C10 1.384(4)
C10 C11 1.392(5)
C11 C12 1.378(5)
C12 C13 1.376(4)
