#------------------------------------------------------------------------------
#$Date: 2016-07-04 15:40:04 +0300 (Mon, 04 Jul 2016) $
#$Revision: 184181 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/20/4032031.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_4032031
loop_
_publ_author_name
'Zou, Gong-Feng'
'Zhang, Shi-Qiang'
'Wang, Jia-Xin'
'Liao, Wei-Wei'
_publ_section_title
;
 Asymmetric Construction of Functionalized 1,2-Dihydropyridine and
 Pyridine Derivatives with Adjacent Stereocenters via a Unified Metal-Free
 Catalytic Approach.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5717
_journal_page_last               5725
_journal_paper_doi               10.1021/acs.joc.6b00791
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_sum            'C27 H22 Br N3 O4'
_chemical_formula_weight         532.39
_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                   11.3822(9)
_cell_length_b                   13.3519(10)
_cell_length_c                   16.9247(13)
_cell_measurement_reflns_used    1765
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.65
_cell_measurement_theta_min      2.35
_cell_volume                     2572.1(3)
_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      296(2)
_diffrn_detector_area_resol_mean 5.0cm
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0697
_diffrn_reflns_av_sigmaI/netI    0.1158
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18943
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    1.635
_exptl_absorpt_correction_T_max  0.7574
_exptl_absorpt_correction_T_min  0.7252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.000(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         6364
_refine_ls_number_restraints     56
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1693
_refine_ls_R_factor_gt           0.0627
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0721P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1788
_reflns_number_gt                2723
_reflns_number_total             6364
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00791_si_001.cif
_cod_data_source_block           y
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4032031
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 0.12599(3) 0.35077(3) 1.14581(2) 0.12001(11) Uani 1 1 d .
C1 C 0.33953(19) 0.54353(14) 1.02071(12) 0.0482(6) Uani 1 1 d .
C2 C 0.2915(2) 0.46072(16) 1.05605(13) 0.0567(7) Uani 1 1 d .
H2 H 0.3272 0.3987 1.0489 0.068 Uiso 1 1 calc R
C3 C 0.1915(2) 0.46702(19) 1.10193(14) 0.0675(8) Uani 1 1 d .
C4 C 0.1365(2) 0.55692(19) 1.11443(13) 0.0726(8) Uani 1 1 d .
H4 H 0.0691 0.5605 1.1454 0.087 Uiso 1 1 calc R
C5 C 0.1829(2) 0.64208(19) 1.08037(13) 0.0684(8) Uani 1 1 d .
H5 H 0.1474 0.7038 1.0891 0.082 Uiso 1 1 calc R
C6 C 0.2812(2) 0.63594(17) 1.03368(12) 0.0589(7) Uani 1 1 d .
H6 H 0.3103 0.6937 1.0100 0.071 Uiso 1 1 calc R
C7 C 0.17244(12) 0.35611(10) 0.83412(8) 0.0628(7) Uani 1 1 d GU
C8 C 0.13931(17) 0.31674(14) 0.76143(8) 0.1066(11) Uani 1 1 d GU
H8 H 0.1880 0.3245 0.7177 0.128 Uiso 1 1 calc R
C9 C 0.0334(2) 0.26573(18) 0.75405(13) 0.1232(12) Uani 1 1 d GU
H9 H 0.0113 0.2394 0.7054 0.148 Uiso 1 1 calc R
C10 C -0.03934(17) 0.2541(2) 0.81936(17) 0.1273(13) Uani 1 1 d GU
H10 H -0.1102 0.2200 0.8144 0.153 Uiso 1 1 calc R
C11 C -0.00622(17) 0.2935(2) 0.89206(14) 0.1805(16) Uani 1 1 d GU
H11 H -0.0549 0.2857 0.9358 0.217 Uiso 1 1 calc R
C12 C 0.09967(16) 0.34447(15) 0.89944(9) 0.1511(13) Uani 1 1 d GU
H12 H 0.1218 0.3708 0.9481 0.181 Uiso 1 1 calc R
C13 C 0.44479(19) 0.53217(15) 0.96752(11) 0.0471(6) Uani 1 1 d .
H13 H 0.4630 0.4605 0.9690 0.057 Uiso 1 1 calc R
C14 C 0.5561(2) 0.58293(16) 0.99650(13) 0.0575(7) Uani 1 1 d .
C15 C 0.5603(3) 0.66408(18) 1.04041(15) 0.0811(9) Uani 1 1 d .
H15A H 0.6323 0.6884 1.0579 0.097 Uiso 1 1 calc R
H15B H 0.4913 0.6972 1.0539 0.097 Uiso 1 1 calc R
C16 C 0.6672(2) 0.5320(2) 0.97596(15) 0.0773(9) Uani 1 1 d .
C17 C 0.8729(3) 0.5434(4) 0.9772(3) 0.169(2) Uani 1 1 d .
H17C H 0.8751 0.4800 1.0039 0.254 Uiso 1 1 calc R
H17B H 0.9338 0.5859 0.9974 0.254 Uiso 1 1 calc R
H17A H 0.8846 0.5332 0.9216 0.254 Uiso 1 1 calc R
C18 C 0.41331(18) 0.55407(14) 0.87796(11) 0.0430(6) Uani 1 1 d .
C19 C 0.40557(19) 0.66380(15) 0.86502(12) 0.0550(7) Uani 1 1 d .
C20 C 0.29469(19) 0.50652(15) 0.85919(13) 0.0480(6) Uani 1 1 d .
C21 C 0.1915(2) 0.56709(16) 0.86313(14) 0.0576(7) Uani 1 1 d .
C22 C 0.2860(2) 0.40847(16) 0.84036(13) 0.0530(7) Uani 1 1 d .
C23 C 0.3931(2) 0.35494(16) 0.82562(14) 0.0686(8) Uani 1 1 d .
H23 H 0.3928 0.2853 0.8247 0.082 Uiso 1 1 calc R
C24 C 0.4937(3) 0.40459(16) 0.81316(15) 0.0659(8) Uani 1 1 d .
H24 H 0.5599 0.3697 0.7966 0.079 Uiso 1 1 calc R
C25 C 0.5965(2) 0.56058(17) 0.79804(15) 0.0662(8) Uani 1 1 d .
C26 C 0.7615(3) 0.5511(3) 0.7126(3) 0.213(2) Uani 1 1 d DU
H26B H 0.7458 0.5726 0.6589 0.255 Uiso 1 1 calc R
H26A H 0.7829 0.6097 0.7432 0.255 Uiso 1 1 calc R
C27 C 0.8489(4) 0.4876(4) 0.7125(4) 0.245(3) Uani 1 1 d DU
H27A H 0.8808 0.4825 0.7649 0.367 Uiso 1 1 calc R
H27C H 0.9088 0.5107 0.6769 0.367 Uiso 1 1 calc R
H27B H 0.8214 0.4231 0.6957 0.367 Uiso 1 1 calc R
N1 N 0.3868(2) 0.74688(13) 0.85775(13) 0.0800(7) Uani 1 1 d .
N2 N 0.1097(2) 0.61602(16) 0.86647(14) 0.0860(8) Uani 1 1 d .
N3 N 0.50056(17) 0.50778(13) 0.82460(10) 0.0521(5) Uani 1 1 d .
O1 O 0.67366(17) 0.44797(15) 0.95170(14) 0.1068(8) Uani 1 1 d .
O2 O 0.76164(17) 0.58945(18) 0.98989(13) 0.1087(8) Uani 1 1 d .
O3 O 0.61893(16) 0.64447(12) 0.81664(10) 0.0816(6) Uani 1 1 d .
O4 O 0.6561(2) 0.50659(14) 0.74572(12) 0.1151(8) Uani 1 1 d .
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
C2 C1 C6 116.6(2)
C2 C1 C13 119.78(18)
C6 C1 C13 123.53(18)
C1 C2 C3 121.7(2)
C4 C3 C2 121.1(2)
C4 C3 Br1 118.85(19)
C2 C3 Br1 120.01(18)
C3 C4 C5 118.9(2)
C6 C5 C4 120.2(2)
C5 C6 C1 121.5(2)
C8 C7 C12 120.0
C8 C7 C22 118.74(12)
C12 C7 C22 121.25(12)
C7 C8 C9 120.0
C10 C9 C8 120.0
C9 C10 C11 120.0
C12 C11 C10 120.0
C11 C12 C7 120.0
C1 C13 C14 115.20(17)
C1 C13 C18 111.92(17)
C14 C13 C18 114.53(17)
C15 C14 C16 118.8(2)
C15 C14 C13 125.5(2)
C16 C14 C13 115.65(19)
O1 C16 O2 123.2(3)
O1 C16 C14 124.4(2)
O2 C16 C14 112.4(2)
N3 C18 C19 111.26(16)
N3 C18 C20 107.07(16)
C19 C18 C20 109.12(17)
N3 C18 C13 110.82(16)
C19 C18 C13 109.67(16)
C20 C18 C13 108.81(16)
N1 C19 C18 172.3(2)
C22 C20 C21 120.0(2)
C22 C20 C18 121.16(19)
C21 C20 C18 118.86(17)
N2 C21 C20 179.5(3)
C20 C22 C23 117.5(2)
C20 C22 C7 122.8(2)
C23 C22 C7 119.78(18)
C24 C23 C22 120.5(2)
C23 C24 N3 121.1(2)
O3 C25 O4 125.2(2)
O3 C25 N3 124.4(2)
O4 C25 N3 110.2(2)
C27 C26 O4 111.3(4)
C25 N3 C24 120.4(2)
C25 N3 C18 121.26(17)
C24 N3 C18 117.42(18)
C16 O2 C17 116.0(3)
C25 O4 C26 117.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C3 1.875(3)
C1 C2 1.371(3)
C1 C6 1.418(3)
C1 C13 1.506(3)
C2 C3 1.381(3)
C3 C4 1.370(4)
C4 C5 1.380(4)
C5 C6 1.372(3)
C7 C8 1.3900
C7 C12 1.3900
C7 C22 1.473(3)
C8 C9 1.3900
C9 C10 1.3900
C10 C11 1.3900
C11 C12 1.3900
C13 C14 1.518(3)
C13 C18 1.585(3)
C14 C15 1.315(3)
C14 C16 1.478(4)
C16 O1 1.197(3)
C16 O2 1.341(3)
C17 O2 1.424(4)
C18 N3 1.478(3)
C18 C19 1.484(3)
C18 C20 1.525(3)
C19 N1 1.136(3)
C20 C22 1.351(3)
C20 C21 1.427(3)
C21 N2 1.139(3)
C22 C23 1.436(3)
C23 C24 1.339(4)
C24 N3 1.394(3)
C25 O3 1.191(3)
C25 O4 1.328(3)
C25 N3 1.375(3)
C26 C27 1.307(5)
C26 O4 1.451(4)
