#------------------------------------------------------------------------------
#$Date: 2019-09-20 17:00:41 +0300 (Fri, 20 Sep 2019) $
#$Revision: 218609 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/34/1513482.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_1513482
loop_
_publ_author_name
'Weng, Jian-Quan'
'Deng, Qiao-Man'
'Wu, Liang'
'Xu, Kai'
'Wu, Hao'
'Liu, Ren-Rong'
'Gao, Jian-Rong'
'Jia, Yi-Xia'
_publ_section_title
;
 Asymmetric Friedel-Crafts Alkylation of α-Substituted β-Nitroacrylates:
 Access to β(2,2)-Amino Acids Bearing Indolic All-Carbon Quaternary
 Stereocenters
;
_journal_coden_ASTM              ORLEF7
_journal_issue                   3
_journal_name_full               'Organic Letters'
_journal_page_first              776
_journal_page_last               779
_journal_paper_doi               10.1021/ol403480v
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C21 H21 Br N2 O4'
_chemical_formula_weight         445.31
_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                 107.322(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.0332(4)
_cell_length_b                   8.4710(4)
_cell_length_c                   12.9591(6)
_cell_measurement_reflns_used    1840
_cell_measurement_temperature    303(2)
_cell_measurement_theta_max      23.4250
_cell_measurement_theta_min      3.8830
_cell_volume                     1051.46(8)
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      303(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4794
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    1.983
_exptl_absorpt_correction_T_max  0.6925
_exptl_absorpt_correction_T_min  0.5877
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.024(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.792
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3371
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.792
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1168
_reflns_number_gt                2727
_reflns_number_total             3371
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol403480v_si_002.cif
_cod_data_source_block           p
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/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 2281 2013-09-26 08:29:07Z andrius 

 Updated bibliographic information.

 Antanas Vaitkus,
 2019-09-20
;
_cod_original_sg_symbol_H-M      'P2(1)   '
_cod_database_code               1513482
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 0.88023(4) 0.89045(6) 0.17084(4) 0.07091(19) Uani 1 1 d .
N2 N 1.5630(4) 0.8871(6) 0.3523(2) 0.0516(7) Uani 1 1 d .
C6 C 1.0329(4) 0.9007(7) 0.1117(3) 0.0480(9) Uani 1 1 d .
O2 O 1.6737(4) 0.9070(6) 0.3338(3) 0.0786(10) Uani 1 1 d .
C3 C 1.2499(4) 0.9013(7) 0.0269(3) 0.0475(9) Uani 1 1 d .
O4 O 1.6687(3) 1.2638(4) 0.3696(2) 0.0444(6) Uani 1 1 d .
C17 C 1.6070(4) 1.2171(5) 0.2694(3) 0.0393(8) Uani 1 1 d .
C12 C 1.3270(5) 1.3834(8) 0.1796(3) 0.0611(10) Uani 1 1 d .
H12A H 1.3541 1.3631 0.1182 0.073 Uiso 1 1 calc R
C9 C 1.4638(4) 1.1397(5) 0.2614(3) 0.0368(8) Uani 1 1 d .
O1 O 1.5188(6) 0.7614(5) 0.3722(4) 0.0912(14) Uani 1 1 d .
C10 C 1.4766(4) 1.0301(5) 0.3574(3) 0.0392(9) Uani 1 1 d .
H10A H 1.5193 1.0870 0.4240 0.047 Uiso 1 1 calc R
H10B H 1.3842 0.9970 0.3577 0.047 Uiso 1 1 calc R
C4 C 1.2638(4) 0.9837(5) 0.1240(3) 0.0388(8) Uani 1 1 d .
C1 C 1.0201(5) 0.8187(6) 0.0155(4) 0.0553(11) Uani 1 1 d .
H1A H 0.9384 0.7643 -0.0187 0.066 Uiso 1 1 calc R
O3 O 1.6501(3) 1.2396(4) 0.1937(2) 0.0552(8) Uani 1 1 d .
C7 C 1.4644(5) 1.0021(6) 0.0815(3) 0.0542(11) Uani 1 1 d .
H7A H 1.5554 1.0260 0.0830 0.065 Uiso 1 1 calc R
N1 N 1.3734(4) 0.9149(6) 0.0035(3) 0.0635(12) Uani 1 1 d .
H1B H 1.3910 0.8745 -0.0519 0.076 Uiso 1 1 calc R
C8 C 1.4032(4) 1.0495(5) 0.1569(3) 0.0398(8) Uani 1 1 d .
C16 C 1.3289(5) 1.3183(6) 0.3579(4) 0.0531(11) Uani 1 1 d .
H16A H 1.3573 1.2541 0.4187 0.064 Uiso 1 1 calc R
C2 C 1.1287(5) 0.8194(6) -0.0280(3) 0.0535(11) Uani 1 1 d .
H2A H 1.1221 0.7667 -0.0923 0.064 Uiso 1 1 calc R
C11 C 1.3691(4) 1.2819(5) 0.2675(3) 0.0394(8) Uani 1 1 d .
C5 C 1.1497(4) 0.9848(5) 0.1659(3) 0.0409(9) Uani 1 1 d .
H5A H 1.1532 1.0407 0.2284 0.049 Uiso 1 1 calc R
C13 C 1.2456(6) 1.5135(7) 0.1819(5) 0.0815(17) Uani 1 1 d .
H13A H 1.2184 1.5804 0.1224 0.098 Uiso 1 1 calc R
C14 C 1.2048(6) 1.5445(7) 0.2715(5) 0.0792(16) Uani 1 1 d .
H14A H 1.1482 1.6311 0.2724 0.095 Uiso 1 1 calc R
C18 C 1.8028(4) 1.3493(5) 0.4001(3) 0.0482(10) Uani 1 1 d .
C21 C 1.8205(7) 1.3895(12) 0.5166(4) 0.112(3) Uani 1 1 d .
H21A H 1.8236 1.2940 0.5572 0.168 Uiso 1 1 calc R
H21B H 1.7432 1.4530 0.5213 0.168 Uiso 1 1 calc R
H21C H 1.9058 1.4472 0.5457 0.168 Uiso 1 1 calc R
C15 C 1.2470(6) 1.4494(7) 0.3587(5) 0.0714(14) Uani 1 1 d .
H15A H 1.2206 1.4722 0.4201 0.086 Uiso 1 1 calc R
C20 C 1.7973(7) 1.4949(6) 0.3324(6) 0.0844(17) Uani 1 1 d .
H20A H 1.7844 1.4649 0.2586 0.127 Uiso 1 1 calc R
H20B H 1.8831 1.5525 0.3590 0.127 Uiso 1 1 calc R
H20C H 1.7208 1.5603 0.3364 0.127 Uiso 1 1 calc R
C19 C 1.9129(6) 1.2368(9) 0.3903(7) 0.098(2) Uani 1 1 d .
H19A H 1.9132 1.1456 0.4343 0.146 Uiso 1 1 calc R
H19B H 2.0025 1.2874 0.4139 0.146 Uiso 1 1 calc R
H19C H 1.8940 1.2049 0.3162 0.146 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
O1 N2 O2 125.4(5)
O1 N2 C10 116.6(3)
O2 N2 C10 118.0(4)
C5 C6 C1 123.4(4)
C5 C6 Br1 118.9(3)
C1 C6 Br1 117.7(3)
N1 C3 C2 129.7(4)
N1 C3 C4 107.5(4)
C2 C3 C4 122.7(3)
C17 O4 C18 122.2(3)
O3 C17 O4 125.3(4)
O3 C17 C9 124.3(3)
O4 C17 C9 110.2(3)
C13 C12 C11 121.0(4)
C8 C9 C10 109.6(3)
C8 C9 C11 110.4(3)
C10 C9 C11 109.6(3)
C8 C9 C17 112.9(3)
C10 C9 C17 110.5(3)
C11 C9 C17 103.7(3)
N2 C10 C9 111.4(3)
C5 C4 C3 118.2(3)
C5 C4 C8 135.3(3)
C3 C4 C8 106.5(3)
C2 C1 C6 119.5(4)
N1 C7 C8 110.3(4)
C7 N1 C3 109.5(3)
C7 C8 C4 106.2(3)
C7 C8 C9 130.1(4)
C4 C8 C9 123.6(3)
C11 C16 C15 120.6(5)
C1 C2 C3 118.1(4)
C16 C11 C12 117.6(4)
C16 C11 C9 123.6(3)
C12 C11 C9 118.7(3)
C6 C5 C4 117.9(3)
C14 C13 C12 120.1(5)
C15 C14 C13 119.9(5)
O4 C18 C19 107.6(4)
O4 C18 C20 112.0(4)
C19 C18 C20 111.9(5)
O4 C18 C21 101.8(3)
C19 C18 C21 111.2(6)
C20 C18 C21 111.8(5)
C14 C15 C16 120.8(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C6 1.908(4)
N2 O1 1.211(7)
N2 O2 1.216(5)
N2 C10 1.503(6)
C6 C5 1.373(6)
C6 C1 1.399(6)
C3 N1 1.365(5)
C3 C2 1.397(6)
C3 C4 1.410(5)
O4 C17 1.322(5)
O4 C18 1.475(5)
C17 O3 1.199(4)
C17 C9 1.554(5)
C12 C13 1.378(8)
C12 C11 1.388(6)
C9 C8 1.516(5)
C9 C10 1.526(5)
C9 C11 1.551(5)
C4 C5 1.405(5)
C4 C8 1.447(5)
C1 C2 1.368(7)
C7 N1 1.360(6)
C7 C8 1.361(5)
C16 C11 1.382(5)
C16 C15 1.384(7)
C13 C14 1.366(8)
C14 C15 1.349(8)
C18 C19 1.493(7)
C18 C20 1.505(7)
C18 C21 1.507(6)
