#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501988.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_1501988
loop_
_publ_author_name
'Hong, Bor-Cherng'
'Dange, Nitin S.'
'Hsu, Che-Sheng'
'Liao, Ju-Hsiou'
'Lee, Gene-Hsiang'
_publ_section_title
;
 Dynamic kinetic asymmetric synthesis of five contiguous stereogenic
 centers by sequential organocatalytic stetter and Michael-aldol reaction:
 enantioselective synthesis of fully substituted cyclopentanols bearing a
 quaternary stereocenter.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1338
_journal_page_last               1341
_journal_paper_doi               10.1021/ol200006e
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration unk
_chemical_formula_sum            'C23 H25 Br N2 O4'
_chemical_formula_weight         473.36
_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                   5.8869(4)
_cell_length_b                   12.4397(9)
_cell_length_c                   30.019(2)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.529
_cell_measurement_theta_min      -23.529
_cell_volume                     2198.3(3)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    Ortep-3
_computing_publication_material  'Wingx publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker Smart Apex'
_diffrn_measurement_method       'phi-omega scan'
_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  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            25670
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.36
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    1.901
_exptl_absorpt_correction_T_max  0.8674
_exptl_absorpt_correction_T_min  0.6448
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       columnar
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.125
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.005(7)
_refine_ls_extinction_coef       0.0012(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         5329
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0527P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0766
_refine_ls_wR_factor_ref         0.0890
_reflns_number_gt                4006
_reflns_number_total             5329
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol200006e_si_003.cif
_cod_data_source_block           hcs2121f1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical'
changed to 'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     P2ac2ab
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1501988
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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 0.70300(7) 1.22589(2) 0.599336(9) 0.07262(14) Uani 1 1 d .
O1 O 0.3227(3) 0.82075(15) 0.36335(6) 0.0496(4) Uani 1 1 d .
H1 H 0.291(7) 0.759(3) 0.3503(13) 0.097(12) Uiso 1 1 d .
O2 O 0.1837(4) 0.83461(19) 0.47030(10) 0.0916(8) Uani 1 1 d .
O3 O 0.6790(6) 1.16495(19) 0.35627(11) 0.1124(10) Uani 1 1 d .
O4 O 0.3824(4) 1.07084(17) 0.34618(8) 0.0782(7) Uani 1 1 d .
N1 N 0.4579(4) 0.62294(18) 0.36083(8) 0.0556(6) Uani 1 1 d .
N2 N 0.5701(5) 1.08332(18) 0.36073(8) 0.0594(6) Uani 1 1 d .
C1 C 0.5435(4) 0.80743(18) 0.38168(8) 0.0377(5) Uani 1 1 d .
C2 C 0.5357(4) 0.84478(18) 0.43122(8) 0.0397(5) Uani 1 1 d .
H2 H 0.6801 0.8263 0.4455 0.048 Uiso 1 1 calc R
C3 C 0.5188(4) 0.96689(19) 0.42744(8) 0.0412(5) Uani 1 1 d .
H3 H 0.366(4) 0.9804(17) 0.4176(7) 0.028(5) Uiso 1 1 d .
C4 C 0.6775(5) 0.99395(18) 0.38765(7) 0.0428(5) Uani 1 1 d .
H4 H 0.8244 1.0185 0.3991 0.051 Uiso 1 1 calc R
C5 C 0.7127(4) 0.88757(18) 0.36099(7) 0.0393(5) Uani 1 1 d .
H5 H 0.8632 0.8615 0.3699 0.047 Uiso 1 1 calc R
C6 C 0.6119(4) 0.68901(19) 0.37851(8) 0.0400(5) Uani 1 1 d .
C7 C 0.8177(4) 0.6546(2) 0.39342(9) 0.0508(6) Uani 1 1 d .
H7 H 0.9208 0.7023 0.4060 0.061 Uiso 1 1 calc R
C8 C 0.8689(5) 0.5468(3) 0.38933(11) 0.0694(9) Uani 1 1 d .
H8 H 1.0091 0.5212 0.3988 0.083 Uiso 1 1 calc R
C9 C 0.7140(7) 0.4780(2) 0.37134(10) 0.0685(9) Uani 1 1 d .
H9 H 0.7462 0.4051 0.3688 0.082 Uiso 1 1 calc R
C10 C 0.5114(6) 0.5179(2) 0.35715(10) 0.0636(8) Uani 1 1 d .
H10 H 0.4064 0.4712 0.3445 0.076 Uiso 1 1 calc R
C11 C 0.7233(5) 0.8971(2) 0.30979(7) 0.0476(6) Uani 1 1 d .
H11 H 0.585(4) 0.9285(18) 0.2996(8) 0.034(6) Uiso 1 1 d .
C12 C 0.7364(6) 0.7879(2) 0.28679(8) 0.0656(8) Uani 1 1 d .
H12A H 0.6026 0.7462 0.2943 0.079 Uiso 1 1 calc R
H12B H 0.8685 0.7493 0.2976 0.079 Uiso 1 1 calc R
C13 C 0.7521(8) 0.7997(3) 0.23606(9) 0.0885(12) Uani 1 1 d .
H13A H 0.7671 0.7292 0.2226 0.106 Uiso 1 1 calc R
H13B H 0.6139 0.8324 0.2249 0.106 Uiso 1 1 calc R
C14 C 0.9521(8) 0.8678(4) 0.22338(11) 0.0971(13) Uani 1 1 d .
H14A H 0.9546 0.8769 0.1913 0.117 Uiso 1 1 calc R
H14B H 1.0910 0.8314 0.2321 0.117 Uiso 1 1 calc R
C15 C 0.9431(8) 0.9770(3) 0.24544(11) 0.0859(11) Uani 1 1 d .
H15A H 0.8128 1.0167 0.2344 0.103 Uiso 1 1 calc R
H15B H 1.0790 1.0173 0.2380 0.103 Uiso 1 1 calc R
C16 C 0.9257(6) 0.9652(3) 0.29589(9) 0.0640(7) Uani 1 1 d .
H16A H 1.0639 0.9325 0.3071 0.077 Uiso 1 1 calc R
H16B H 0.9122 1.0360 0.3092 0.077 Uiso 1 1 calc R
C17 C 0.5672(4) 1.02923(18) 0.46951(8) 0.0406(5) Uani 1 1 d .
C18 C 0.7718(4) 1.0206(2) 0.49186(8) 0.0513(6) Uani 1 1 d .
H18 H 0.8835 0.9749 0.4809 0.062 Uiso 1 1 calc R
C19 C 0.8132(5) 1.0788(2) 0.53028(8) 0.0541(6) Uani 1 1 d .
H19 H 0.9511 1.0719 0.5451 0.065 Uiso 1 1 calc R
C20 C 0.6489(5) 1.1469(2) 0.54627(8) 0.0500(7) Uani 1 1 d .
C21 C 0.4452(5) 1.1577(2) 0.52500(8) 0.0524(6) Uani 1 1 d .
H21 H 0.3351 1.2042 0.5360 0.063 Uiso 1 1 calc R
C22 C 0.4045(5) 1.09841(19) 0.48674(8) 0.0468(6) Uani 1 1 d .
H22 H 0.2654 1.1051 0.4723 0.056 Uiso 1 1 calc R
C23 C 0.3469(5) 0.7917(2) 0.45604(9) 0.0530(6) Uani 1 1 d .
H23 H 0.3636 0.7132 0.4589 0.064 Uiso 1 1 d 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
C1 O1 H1 105(3)
C6 N1 C10 118.1(3)
O4 N2 O3 123.9(3)
O4 N2 C4 119.0(2)
O3 N2 C4 117.1(3)
O1 C1 C6 109.21(19)
O1 C1 C5 111.11(19)
C6 C1 C5 115.30(19)
O1 C1 C2 107.92(19)
C6 C1 C2 110.74(19)
C5 C1 C2 102.17(18)
C23 C2 C3 115.4(2)
C23 C2 C1 111.5(2)
C3 C2 C1 103.15(19)
C23 C2 H2 108.8
C3 C2 H2 108.8
C1 C2 H2 108.8
C17 C3 C2 115.9(2)
C17 C3 C4 114.7(2)
C2 C3 C4 103.52(18)
C17 C3 H3 110.1(12)
C2 C3 H3 104.9(13)
C4 C3 H3 106.8(12)
N2 C4 C3 108.6(2)
N2 C4 C5 113.88(18)
C3 C4 C5 106.90(18)
N2 C4 H4 109.1
C3 C4 H4 109.1
C5 C4 H4 109.1
C1 C5 C11 118.5(2)
C1 C5 C4 104.83(18)
C11 C5 C4 116.81(19)
C1 C5 H5 105.1
C11 C5 H5 105.1
C4 C5 H5 105.1
N1 C6 C7 122.8(2)
N1 C6 C1 116.0(2)
C7 C6 C1 121.1(2)
C6 C7 C8 118.1(3)
C6 C7 H7 120.9
C8 C7 H7 120.9
C9 C8 C7 120.0(3)
C9 C8 H8 120.0
C7 C8 H8 120.0
C10 C9 C8 118.8(3)
C10 C9 H9 120.6
C8 C9 H9 120.6
N1 C10 C9 122.2(3)
N1 C10 H10 118.9
C9 C10 H10 118.9
C16 C11 C12 109.4(2)
C16 C11 C5 110.4(2)
C12 C11 C5 112.6(2)
C16 C11 H11 110.8(14)
C12 C11 H11 105.2(14)
C5 C11 H11 108.4(14)
C11 C12 C13 111.6(2)
C11 C12 H12A 109.3
C13 C12 H12A 109.3
C11 C12 H12B 109.3
C13 C12 H12B 109.3
H12A C12 H12B 108.0
C14 C13 C12 110.7(3)
C14 C13 H13A 109.5
C12 C13 H13A 109.5
C14 C13 H13B 109.5
C12 C13 H13B 109.5
H13A C13 H13B 108.1
C13 C14 C15 111.7(3)
C13 C14 H14A 109.3
C15 C14 H14A 109.3
C13 C14 H14B 109.3
C15 C14 H14B 109.3
H14A C14 H14B 107.9
C14 C15 C16 110.5(3)
C14 C15 H15A 109.5
C16 C15 H15A 109.5
C14 C15 H15B 109.5
C16 C15 H15B 109.5
H15A C15 H15B 108.1
C11 C16 C15 112.3(3)
C11 C16 H16A 109.2
C15 C16 H16A 109.2
C11 C16 H16B 109.2
C15 C16 H16B 109.2
H16A C16 H16B 107.9
C18 C17 C22 117.9(2)
C18 C17 C3 122.1(2)
C22 C17 C3 120.0(2)
C17 C18 C19 121.2(2)
C17 C18 H18 119.4
C19 C18 H18 119.4
C20 C19 C18 119.4(2)
C20 C19 H19 120.3
C18 C19 H19 120.3
C21 C20 C19 121.1(2)
C21 C20 Br1 119.3(2)
C19 C20 Br1 119.7(2)
C20 C21 C22 119.2(3)
C20 C21 H21 120.4
C22 C21 H21 120.4
C21 C22 C17 121.3(3)
C21 C22 H22 119.3
C17 C22 H22 119.3
O2 C23 C2 126.0(3)
O2 C23 H23 119.9
C2 C23 H23 114.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C20 1.898(2)
O1 C1 1.421(3)
O1 H1 0.89(4)
O2 C23 1.179(3)
O3 N2 1.208(3)
O4 N2 1.198(3)
N1 C6 1.334(3)
N1 C10 1.348(4)
N2 C4 1.513(3)
C1 C6 1.530(3)
C1 C5 1.540(3)
C1 C2 1.559(3)
C2 C23 1.492(4)
C2 C3 1.526(3)
C2 H2 0.9800
C3 C17 1.509(3)
C3 C4 1.553(3)
C3 H3 0.96(2)
C4 C5 1.560(3)
C4 H4 0.9800
C5 C11 1.543(3)
C5 H5 0.9800
C6 C7 1.360(4)
C7 C8 1.379(4)
C7 H7 0.9300
C8 C9 1.362(5)
C8 H8 0.9300
C9 C10 1.360(5)
C9 H9 0.9300
C10 H10 0.9300
C11 C16 1.520(4)
C11 C12 1.526(4)
C11 H11 0.95(2)
C12 C13 1.533(4)
C12 H12A 0.9700
C12 H12B 0.9700
C13 C14 1.499(6)
C13 H13A 0.9700
C13 H13B 0.9700
C14 C15 1.513(5)
C14 H14A 0.9700
C14 H14B 0.9700
C15 C16 1.525(4)
C15 H15A 0.9700
C15 H15B 0.9700
C16 H16A 0.9700
C16 H16B 0.9700
C17 C18 1.383(4)
C17 C22 1.388(3)
C18 C19 1.383(3)
C18 H18 0.9300
C19 C20 1.372(4)
C19 H19 0.9300
C20 C21 1.365(4)
C21 C22 1.386(4)
C21 H21 0.9300
C22 H22 0.9300
C23 H23 0.9856
