#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/81/1518151.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_1518151
loop_
_publ_author_name
'He, Ling'
'Zhao, Liang'
'Wang, De-Xian'
'Wang, Mei-Xiang'
_publ_section_title
;
 Catalytic asymmetric difunctionalization of stable tertiary enamides with
 salicylaldehydes: highly efficient, enantioselective, and
 diastereoselective synthesis of diverse 4-chromanol derivatives.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5972
_journal_page_last               5975
_journal_paper_doi               10.1021/ol5029964
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H16 Br N O3'
_chemical_formula_sum            'C18 H16 Br N O3'
_chemical_formula_weight         374.23
_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                   5.9343(12)
_cell_length_b                   11.372(2)
_cell_length_c                   23.049(5)
_cell_measurement_reflns_used    4501
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.77
_cell_volume                     1555.5(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 ver 1.1'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'Olex2 ver 1.1'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9791
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.20
_exptl_absorpt_coefficient_mu    2.658
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.018(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3553
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0347
_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)+(0.0343P)²+0.3781P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0802
_reflns_number_gt                3366
_reflns_number_total             3553
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5029964_si_003.cif
_cod_data_source_block           sa2887
_cod_depositor_comments
'Adding full bibliography for 1518151--1518152.cif.'
_cod_original_cell_volume        1555.4(6)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1518151
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 -0.09130(5) 0.14530(3) 0.585116(13) 0.04583(11) Uani 1 1 d .
O1 O 0.4372(3) 0.58327(16) 0.63944(7) 0.0302(4) Uani 1 1 d .
O2 O -0.0991(3) 0.49542(17) 0.74909(7) 0.0315(4) Uani 1 1 d .
H2 H -0.0070 0.4542 0.7678 0.047 Uiso 1 1 calc R
O3 O 0.8309(3) 0.84493(18) 0.68999(8) 0.0368(4) Uani 1 1 d .
N1 N 0.5017(4) 0.7480(2) 0.69529(9) 0.0286(5) Uani 1 1 d .
C1 C 0.3251(4) 0.6803(2) 0.66835(11) 0.0278(5) Uani 1 1 d .
H1 H 0.2347 0.7287 0.6406 0.033 Uiso 1 1 calc R
C2 C 0.1849(4) 0.6399(2) 0.71963(10) 0.0270(5) Uani 1 1 d .
H2A H 0.1018 0.7097 0.7351 0.032 Uiso 1 1 calc R
C3 C 0.0124(4) 0.5489(2) 0.70156(10) 0.0263(5) Uani 1 1 d .
H3 H -0.1060 0.5922 0.6793 0.032 Uiso 1 1 calc R
C4 C 0.1123(4) 0.4593(2) 0.65999(10) 0.0259(5) Uani 1 1 d .
C5 C 0.3160(4) 0.4816(2) 0.63185(11) 0.0257(5) Uani 1 1 d .
C6 C 0.4061(5) 0.3994(2) 0.59336(10) 0.0302(5) Uani 1 1 d .
H6 H 0.5484 0.4137 0.5759 0.036 Uiso 1 1 calc R
C7 C 0.2906(5) 0.2981(2) 0.58060(12) 0.0330(6) Uani 1 1 d .
H7 H 0.3519 0.2421 0.5544 0.040 Uiso 1 1 calc R
C8 C 0.0826(5) 0.2788(2) 0.60665(11) 0.0312(5) Uani 1 1 d .
C9 C -0.0036(4) 0.3566(2) 0.64663(10) 0.0283(5) Uani 1 1 d .
H9 H -0.1429 0.3400 0.6652 0.034 Uiso 1 1 calc R
C10 C 0.3701(4) 0.6081(2) 0.76320(11) 0.0314(6) Uani 1 1 d .
H10A H 0.3099 0.6038 0.8032 0.038 Uiso 1 1 calc R
H10B H 0.4420 0.5322 0.7533 0.038 Uiso 1 1 calc R
C11 C 0.5351(5) 0.7101(3) 0.75651(11) 0.0312(6) Uani 1 1 d .
H11A H 0.4991 0.7746 0.7838 0.037 Uiso 1 1 calc R
H11B H 0.6921 0.6840 0.7632 0.037 Uiso 1 1 calc R
C12 C 0.6528(4) 0.8148(2) 0.66684(11) 0.0285(5) Uani 1 1 d .
C13 C 0.6015(4) 0.8523(2) 0.60604(11) 0.0278(5) Uani 1 1 d .
C14 C 0.4061(5) 0.9140(2) 0.59216(12) 0.0338(6) Uani 1 1 d .
H14 H 0.2969 0.9299 0.6213 0.041 Uiso 1 1 calc R
C15 C 0.3714(5) 0.9521(3) 0.53570(13) 0.0390(7) Uani 1 1 d .
H15 H 0.2379 0.9939 0.5261 0.047 Uiso 1 1 calc R
C16 C 0.5303(5) 0.9296(3) 0.49332(13) 0.0407(7) Uani 1 1 d .
H16 H 0.5060 0.9560 0.4547 0.049 Uiso 1 1 calc R
C17 C 0.7254(5) 0.8684(3) 0.50705(13) 0.0414(7) Uani 1 1 d .
H17 H 0.8339 0.8522 0.4778 0.050 Uiso 1 1 calc R
C18 C 0.7610(5) 0.8314(3) 0.56322(13) 0.0369(6) Uani 1 1 d .
H18 H 0.8963 0.7912 0.5727 0.044 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'
Br Br -0.2901 2.4595 '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
C5 O1 C1 117.32(19)
C3 O2 H2 109.5
C12 N1 C1 125.2(2)
C12 N1 C11 122.4(2)
C1 N1 C11 110.5(2)
N1 C1 O1 105.7(2)
N1 C1 C2 103.0(2)
O1 C1 C2 112.3(2)
N1 C1 H1 111.8
O1 C1 H1 111.8
C2 C1 H1 111.8
C3 C2 C1 111.3(2)
C3 C2 C10 120.3(2)
C1 C2 C10 100.9(2)
C3 C2 H2A 107.9
C1 C2 H2A 107.9
C10 C2 H2A 107.9
O2 C3 C2 113.4(2)
O2 C3 C4 112.5(2)
C2 C3 C4 111.6(2)
O2 C3 H3 106.3
C2 C3 H3 106.3
C4 C3 H3 106.3
C9 C4 C5 118.6(2)
C9 C4 C3 120.7(2)
C5 C4 C3 120.7(2)
O1 C5 C4 123.2(2)
O1 C5 C6 116.4(2)
C4 C5 C6 120.4(2)
C7 C6 C5 120.5(3)
C7 C6 H6 119.8
C5 C6 H6 119.8
C6 C7 C8 118.9(3)
C6 C7 H7 120.5
C8 C7 H7 120.5
C9 C8 C7 121.2(3)
C9 C8 Br1 119.1(2)
C7 C8 Br1 119.7(2)
C8 C9 C4 120.3(2)
C8 C9 H9 119.8
C4 C9 H9 119.8
C11 C10 C2 102.4(2)
C11 C10 H10A 111.3
C2 C10 H10A 111.3
C11 C10 H10B 111.3
C2 C10 H10B 111.3
H10A C10 H10B 109.2
N1 C11 C10 103.3(2)
N1 C11 H11A 111.1
C10 C11 H11A 111.1
N1 C11 H11B 111.1
C10 C11 H11B 111.1
H11A C11 H11B 109.1
O3 C12 N1 121.2(2)
O3 C12 C13 120.0(2)
N1 C12 C13 118.8(2)
C18 C13 C14 119.4(2)
C18 C13 C12 118.6(2)
C14 C13 C12 121.9(2)
C15 C14 C13 119.8(3)
C15 C14 H14 120.1
C13 C14 H14 120.1
C16 C15 C14 120.3(3)
C16 C15 H15 119.9
C14 C15 H15 119.9
C15 C16 C17 120.1(3)
C15 C16 H16 120.0
C17 C16 H16 120.0
C18 C17 C16 119.7(3)
C18 C17 H17 120.1
C16 C17 H17 120.1
C17 C18 C13 120.8(3)
C17 C18 H18 119.6
C13 C18 H18 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C8 1.902(3)
O1 C5 1.372(3)
O1 C1 1.450(3)
O2 C3 1.417(3)
O2 H2 0.8400
O3 C12 1.233(3)
N1 C12 1.346(3)
N1 C1 1.441(3)
N1 C11 1.489(3)
C1 C2 1.517(3)
C1 H1 1.0000
C2 C3 1.514(4)
C2 C10 1.532(3)
C2 H2A 1.0000
C3 C4 1.519(3)
C3 H3 1.0000
C4 C9 1.390(4)
C4 C5 1.395(4)
C5 C6 1.395(4)
C6 C7 1.372(4)
C6 H6 0.9500
C7 C8 1.391(4)
C7 H7 0.9500
C8 C9 1.376(4)
C9 H9 0.9500
C10 C11 1.526(4)
C10 H10A 0.9900
C10 H10B 0.9900
C11 H11A 0.9900
C11 H11B 0.9900
C12 C13 1.496(4)
C13 C18 1.388(4)
C13 C14 1.393(4)
C14 C15 1.387(4)
C14 H14 0.9500
C15 C16 1.382(4)
C15 H15 0.9500
C16 C17 1.386(4)
C16 H16 0.9500
C17 C18 1.378(4)
C17 H17 0.9500
C18 H18 0.9500
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C12 N1 C1 O1 71.0(3)
C11 N1 C1 O1 -93.8(2)
C12 N1 C1 C2 -171.0(2)
C11 N1 C1 C2 24.2(3)
C5 O1 C1 N1 152.9(2)
C5 O1 C1 C2 41.3(3)
N1 C1 C2 C3 -169.9(2)
O1 C1 C2 C3 -56.6(3)
N1 C1 C2 C10 -41.1(2)
O1 C1 C2 C10 72.1(3)
C1 C2 C3 O2 170.9(2)
C10 C2 C3 O2 53.4(3)
C1 C2 C3 C4 42.7(3)
C10 C2 C3 C4 -74.8(3)
O2 C3 C4 C9 39.2(3)
C2 C3 C4 C9 167.9(2)
O2 C3 C4 C5 -144.5(2)
C2 C3 C4 C5 -15.8(3)
C1 O1 C5 C4 -13.0(3)
C1 O1 C5 C6 166.4(2)
C9 C4 C5 O1 176.2(2)
C3 C4 C5 O1 -0.1(3)
C9 C4 C5 C6 -3.2(3)
C3 C4 C5 C6 -179.5(2)
O1 C5 C6 C7 -176.4(2)
C4 C5 C6 C7 3.1(4)
C5 C6 C7 C8 0.0(4)
C6 C7 C8 C9 -2.9(4)
C6 C7 C8 Br1 175.1(2)
C7 C8 C9 C4 2.8(4)
Br1 C8 C9 C4 -175.26(18)
C5 C4 C9 C8 0.3(4)
C3 C4 C9 C8 176.6(2)
C3 C2 C10 C11 165.7(2)
C1 C2 C10 C11 43.0(2)
C12 N1 C11 C10 -162.3(2)
C1 N1 C11 C10 3.0(3)
C2 C10 C11 N1 -28.6(2)
C1 N1 C12 O3 -160.8(2)
C11 N1 C12 O3 2.2(4)
C1 N1 C12 C13 19.1(4)
C11 N1 C12 C13 -177.9(2)
O3 C12 C13 C18 51.9(3)
N1 C12 C13 C18 -128.0(3)
O3 C12 C13 C14 -123.8(3)
N1 C12 C13 C14 56.3(3)
C18 C13 C14 C15 1.1(4)
C12 C13 C14 C15 176.7(2)
C13 C14 C15 C16 -0.3(4)
C14 C15 C16 C17 0.1(5)
C15 C16 C17 C18 -0.7(5)
C16 C17 C18 C13 1.5(5)
C14 C13 C18 C17 -1.7(4)
C12 C13 C18 C17 -177.5(3)
