#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/65/1506528.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_1506528
loop_
_publ_author_name
'Wipf, Peter'
'Stephenson, Corey R. J.'
_publ_section_title
;
 Three-component synthesis of alpha,beta-cyclopropyl-gamma-amino acids.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1137
_journal_page_last               1140
_journal_paper_doi               10.1021/ol0501525
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C19 H18 Br N O3'
_chemical_formula_weight         388.25
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_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                   5.3668(3)
_cell_length_b                   14.3480(7)
_cell_length_c                   23.0874(11)
_cell_measurement_temperature    571(2)
_cell_volume                     1777.80(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      571(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0780
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            23271
_diffrn_reflns_theta_full        32.50
_diffrn_reflns_theta_max         32.50
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    2.328
_exptl_absorpt_correction_T_max  0.6532
_exptl_absorpt_correction_T_min  0.6532
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.000(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         6280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.955
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.492
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0297P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.1043
_reflns_number_gt                3462
_reflns_number_total             6280
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0501525si20050122_030349.cif
_cod_data_source_block           corey70s
_cod_database_code               1506528
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
Br Br 0.05403(7) 0.85231(2) 0.010083(12) 0.06441(12) Uani 1 1 d .
O1 O 0.5378(3) 0.86020(15) -0.26582(8) 0.0530(4) Uani 1 1 d .
O2 O -0.4945(3) 1.07224(17) -0.35384(10) 0.0664(6) Uani 1 1 d .
O3 O -0.2742(4) 1.09277(16) -0.27247(11) 0.0629(6) Uani 1 1 d .
N N 0.1264(4) 0.85524(19) -0.28419(9) 0.0437(5) Uani 1 1 d .
H1N H -0.014(6) 0.863(2) -0.2732(12) 0.045(8) Uiso 1 1 d .
C1 C 0.0569(6) 0.8000(2) -0.16552(11) 0.0512(6) Uani 1 1 d .
H1A H -0.0433 0.7679 -0.1916 0.061 Uiso 1 1 calc R
C2 C -0.0017(6) 0.7987(2) -0.10723(12) 0.0557(8) Uani 1 1 d .
H2A H -0.1400 0.7657 -0.0942 0.067 Uiso 1 1 calc R
C3 C 0.1458(5) 0.8464(2) -0.06887(10) 0.0475(6) Uani 1 1 d .
C4 C 0.3570(6) 0.8914(2) -0.08779(12) 0.0565(8) Uani 1 1 d .
H4A H 0.4607 0.9212 -0.0613 0.068 Uiso 1 1 calc R
C5 C 0.4148(5) 0.8926(2) -0.14578(12) 0.0509(7) Uani 1 1 d .
H5A H 0.5574 0.9232 -0.1585 0.061 Uiso 1 1 calc R
C6 C 0.2610(4) 0.8481(2) -0.18543(10) 0.0395(5) Uani 1 1 d .
C7 C 0.3222(4) 0.8550(2) -0.24880(10) 0.0390(5) Uani 1 1 d .
C8 C 0.1448(4) 0.86796(18) -0.34722(10) 0.0392(6) Uani 1 1 d .
H8A H 0.2992 0.9018 -0.3556 0.047 Uiso 1 1 calc R
C9 C -0.0694(5) 0.92644(18) -0.36643(10) 0.0418(6) Uani 1 1 d .
H9A H -0.2327 0.8962 -0.3636 0.050 Uiso 1 1 calc R
C10 C -0.0492(7) 0.9984(2) -0.41229(12) 0.0642(8) Uani 1 1 d .
H10A H -0.1932 1.0086 -0.4369 0.077 Uiso 1 1 calc R
H10B H 0.1103 1.0054 -0.4316 0.077 Uiso 1 1 calc R
C11 C -0.0671(5) 1.02861(19) -0.35070(13) 0.0513(7) Uani 1 1 d .
H11A H 0.0867 1.0522 -0.3331 0.062 Uiso 1 1 calc R
C12 C -0.3018(5) 1.0672(2) -0.32787(13) 0.0499(7) Uani 1 1 d .
C13 C -0.4998(7) 1.1206(3) -0.24335(18) 0.0792(11) Uani 1 1 d .
H13A H -0.4623 1.1370 -0.2040 0.119 Uiso 1 1 calc R
H13B H -0.6166 1.0699 -0.2438 0.119 Uiso 1 1 calc R
H13C H -0.5708 1.1734 -0.2628 0.119 Uiso 1 1 calc R
C14 C 0.1533(5) 0.7757(2) -0.37867(11) 0.0458(6) Uani 1 1 d .
C15 C 0.3171(6) 0.7604(3) -0.42300(15) 0.0737(10) Uani 1 1 d .
H15A H 0.4306 0.8066 -0.4330 0.088 Uiso 1 1 calc R
C16 C 0.3168(9) 0.6768(3) -0.45339(19) 0.0968(14) Uani 1 1 d .
H16A H 0.4279 0.6684 -0.4839 0.116 Uiso 1 1 calc R
C17 C 0.1585(9) 0.6082(3) -0.4394(2) 0.0920(13) Uani 1 1 d .
H17A H 0.1605 0.5522 -0.4597 0.110 Uiso 1 1 calc R
C18 C -0.0056(10) 0.6213(3) -0.3951(2) 0.1039(15) Uani 1 1 d .
H18A H -0.1160 0.5741 -0.3849 0.125 Uiso 1 1 calc R
C19 C -0.0078(8) 0.7054(3) -0.36508(16) 0.0813(11) Uani 1 1 d .
H19A H -0.1215 0.7139 -0.3351 0.098 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
C12 O3 C13 115.4(3)
C7 N C8 123.7(2)
C6 C1 C2 120.9(3)
C3 C2 C1 119.4(3)
C2 C3 C4 120.3(2)
C2 C3 Br 119.7(2)
C4 C3 Br 120.0(2)
C5 C4 C3 120.0(3)
C4 C5 C6 120.2(3)
C1 C6 C5 119.0(2)
C1 C6 C7 122.2(2)
C5 C6 C7 118.8(2)
O1 C7 N 123.3(2)
O1 C7 C6 121.5(2)
N C7 C6 115.2(2)
N C8 C9 108.2(2)
N C8 C14 111.7(2)
C9 C8 C14 111.9(2)
C10 C9 C8 123.2(3)
C10 C9 C11 59.68(19)
C8 C9 C11 117.9(2)
C9 C10 C11 61.07(17)
C12 C11 C10 120.4(3)
C12 C11 C9 116.3(2)
C10 C11 C9 59.26(18)
O2 C12 O3 123.9(3)
O2 C12 C11 125.6(3)
O3 C12 C11 110.5(3)
C19 C14 C15 117.4(3)
C19 C14 C8 121.2(3)
C15 C14 C8 121.3(3)
C14 C15 C16 121.1(4)
C17 C16 C15 120.9(4)
C16 C17 C18 119.2(4)
C17 C18 C19 120.0(4)
C14 C19 C18 121.4(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br C3 1.890(2)
O1 C7 1.224(3)
O2 C12 1.198(3)
O3 C12 1.339(4)
O3 C13 1.441(4)
N C7 1.331(3)
N C8 1.470(3)
C1 C6 1.374(4)
C1 C2 1.382(4)
C2 C3 1.371(4)
C3 C4 1.376(4)
C4 C5 1.374(4)
C5 C6 1.388(4)
C6 C7 1.503(3)
C8 C9 1.491(4)
C8 C14 1.511(4)
C9 C10 1.483(4)
C9 C11 1.510(4)
C10 C11 1.490(4)
C11 C12 1.474(4)
C14 C19 1.365(4)
C14 C15 1.367(4)
C15 C16 1.389(5)
C16 C17 1.341(6)
C17 C18 1.363(6)
C18 C19 1.391(5)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 21200105 ChemSpider
