#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:20:39 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178809 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/63/4106385.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_4106385
loop_
_publ_author_name
'Daniel A. DiRocco'
'Tomislav Rovis'
_publ_section_title
;
 Catalytic Asymmetric Intermolecular Stetter Reaction of Enals with
 Nitroalkenes: Enhancement of Catalytic Efficiency through Bifunctional
 Additives
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10402
_journal_page_last               10405
_journal_paper_doi               10.1021/ja203810b
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H20 Br N O3'
_chemical_formula_weight         366.25
_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                   5.8072(3)
_cell_length_b                   12.3826(5)
_cell_length_c                   22.3700(9)
_cell_measurement_reflns_used    9483
_cell_measurement_temperature    120
_cell_measurement_theta_max      31.61
_cell_measurement_theta_min      4.28
_cell_volume                     1608.59(12)
_computing_cell_refinement       'APEX2 (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'APEX2 (Bruker, 2009)'
_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      120
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0569
_diffrn_reflns_av_sigmaI/netI    0.0555
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            43252
_diffrn_reflns_theta_full        33.31
_diffrn_reflns_theta_max         33.31
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    2.567
_exptl_absorpt_correction_T_max  0.8209
_exptl_absorpt_correction_T_min  0.5628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick, G. M. (2008) SADABS. University of Göttingen, Germany.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.320
_refine_diff_density_min         -1.802
_refine_diff_density_rms         0.454
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.003(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         6182
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.179
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0379
_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)+(0.0936P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.1594
_reflns_number_gt                5135
_reflns_number_total             6182
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja203810b_si_002.cif
_cod_data_source_block           rovis101_0m
_cod_database_code               4106385
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 0.71686(7) 0.02537(3) -0.037405(15) 0.02411(11) Uani 1 1 d .
C1 C 0.6344(6) 0.1143(2) 0.02802(13) 0.0152(6) Uani 1 1 d .
C2 C 0.4216(6) 0.0992(3) 0.05598(14) 0.0173(6) Uani 1 1 d .
H2 H 0.3214 0.0452 0.0433 0.021 Uiso 1 1 calc R
C3 C 0.3635(6) 0.1669(2) 0.10323(14) 0.0157(5) Uani 1 1 d .
H3 H 0.2229 0.1574 0.1224 0.019 Uiso 1 1 calc R
C4 C 0.5115(5) 0.2489(2) 0.12259(13) 0.0128(5) Uani 1 1 d .
C5 C 0.7239(6) 0.2625(2) 0.09324(14) 0.0160(5) Uani 1 1 d .
H5 H 0.8238 0.3168 0.1055 0.019 Uiso 1 1 calc R
C6 C 0.7857(6) 0.1954(2) 0.04595(13) 0.0161(5) Uani 1 1 d .
H6 H 0.9261 0.2046 0.0266 0.019 Uiso 1 1 calc R
C7 C 0.4390(6) 0.3138(2) 0.17421(14) 0.0146(5) Uani 1 1 d .
H7 H 0.2939 0.2991 0.1898 0.018 Uiso 1 1 calc R
C8 C 0.5602(6) 0.3918(2) 0.20110(14) 0.0150(5) Uani 1 1 d .
H8 H 0.7019 0.4099 0.1846 0.018 Uiso 1 1 calc R
C9 C 0.4865(5) 0.4510(2) 0.25474(14) 0.0128(5) Uani 1 1 d .
C10 C 0.2629(5) 0.4230(2) 0.28754(12) 0.0115(5) Uani 1 1 d .
H10 H 0.1628 0.3805 0.2613 0.014 Uiso 1 1 calc R
C11 C 0.3196(5) 0.3571(2) 0.34476(13) 0.0125(5) Uani 1 1 d .
H11 H 0.4167 0.4021 0.3705 0.015 Uiso 1 1 calc R
C12 C 0.0998(6) 0.3288(3) 0.37989(14) 0.0177(6) Uani 1 1 d .
H12A H 0.0228 0.3949 0.3918 0.021 Uiso 1 1 calc R
H12B H -0.0042 0.2886 0.3542 0.021 Uiso 1 1 calc R
C13 C 0.1541(6) 0.2617(3) 0.43543(15) 0.0198(6) Uani 1 1 d .
H13A H 0.2427 0.3050 0.4633 0.024 Uiso 1 1 calc R
H13B H 0.0114 0.2413 0.4549 0.024 Uiso 1 1 calc R
C14 C 0.2896(7) 0.1601(3) 0.41979(14) 0.0217(6) Uani 1 1 d .
H14A H 0.3293 0.1218 0.4562 0.026 Uiso 1 1 calc R
H14B H 0.1949 0.1129 0.3955 0.026 Uiso 1 1 calc R
C15 C 0.5087(7) 0.1887(3) 0.38582(17) 0.0240(7) Uani 1 1 d .
H15A H 0.5883 0.1229 0.3746 0.029 Uiso 1 1 calc R
H15B H 0.6099 0.2301 0.4116 0.029 Uiso 1 1 calc R
C16 C 0.4551(6) 0.2545(3) 0.32959(15) 0.0176(6) Uani 1 1 d .
H16A H 0.3661 0.2106 0.3021 0.021 Uiso 1 1 calc R
H16B H 0.5980 0.2741 0.3100 0.021 Uiso 1 1 calc R
C17 C 0.1415(5) 0.5262(2) 0.30557(13) 0.0139(5) Uani 1 1 d .
H17A H -0.0032 0.5079 0.3247 0.017 Uiso 1 1 calc R
H17B H 0.2356 0.5641 0.3346 0.017 Uiso 1 1 calc R
N1 N 0.0942(5) 0.5999(2) 0.25425(13) 0.0162(5) Uani 1 1 d .
O1 O 0.6083(4) 0.5231(2) 0.27462(11) 0.0193(4) Uani 1 1 d .
O2 O 0.0999(5) 0.5633(2) 0.20317(11) 0.0238(5) Uani 1 1 d .
O3 O 0.0471(5) 0.69425(19) 0.26598(13) 0.0239(5) 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
C6 C1 C2 121.7(3)
C6 C1 Br1 118.8(2)
C2 C1 Br1 119.5(2)
C3 C2 C1 118.3(3)
C2 C3 C4 121.6(3)
C3 C4 C5 118.7(3)
C3 C4 C7 117.7(3)
C5 C4 C7 123.5(3)
C6 C5 C4 120.6(3)
C5 C6 C1 119.1(3)
C8 C7 C4 126.7(3)
C7 C8 C9 125.0(3)
O1 C9 C8 119.5(3)
O1 C9 C10 118.8(3)
C8 C9 C10 121.7(3)
C17 C10 C9 109.4(2)
C17 C10 C11 108.8(2)
C9 C10 C11 109.5(2)
C16 C11 C12 110.5(2)
C16 C11 C10 111.2(2)
C12 C11 C10 111.4(2)
C13 C12 C11 111.6(3)
C14 C13 C12 111.6(3)
C15 C14 C13 110.7(3)
C14 C15 C16 111.3(3)
C15 C16 C11 111.3(3)
N1 C17 C10 113.4(2)
O3 N1 O2 123.7(3)
O3 N1 C17 117.3(3)
O2 N1 C17 119.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.893(3)
C1 C6 1.393(5)
C1 C2 1.398(5)
C2 C3 1.391(4)
C3 C4 1.399(4)
C4 C5 1.408(5)
C4 C7 1.468(4)
C5 C6 1.392(4)
C7 C8 1.338(4)
C8 C9 1.470(4)
C9 O1 1.223(4)
C9 C10 1.531(4)
C10 C17 1.514(4)
C10 C11 1.554(4)
C11 C16 1.532(4)
C11 C12 1.539(4)
C12 C13 1.528(5)
C13 C14 1.524(5)
C14 C15 1.524(5)
C15 C16 1.530(5)
C17 N1 1.492(4)
N1 O3 1.228(3)
N1 O2 1.230(4)
