#------------------------------------------------------------------------------
#$Date: 2020-09-02 19:55:10 +0300 (Wed, 02 Sep 2020) $
#$Revision: 255805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/46/4024600.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_4024600
loop_
_publ_author_name
'Grier A. Wallace'
'Thomas D. Gordon'
'Martin E. Hayes'
'Donald B. Konopacki'
'Shannon R. Fix-Stenzel'
'Xiaolei Zhang'
'Pintipa Grongsaard'
'Kevin P. Cusack'
'Lisa M. Schaffter'
'Rodger F. Henry'
'Robert H. Stoffel'
_publ_section_title
;
Scalable Synthesis and Isolation of the Four Stereoisomers of Methyl
1-Amino-3-(4-bromophenyl)cyclopentanecarboxylate, Useful Intermediates for
the Synthesis of S1P1 Receptor Agonists
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4886
_journal_page_last               4889
_journal_paper_doi               10.1021/jo900376b
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         '2(C13 H17 Br N O2), C4 H4 O6'
_chemical_formula_sum            'C30 H38 Br2 N2 O10'
_chemical_formula_weight         746.44
_chemical_name_systematic
; 
 ? 
;
_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                 107.461(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   15.900(4)
_cell_length_b                   6.2937(17)
_cell_length_c                   16.234(4)
_cell_measurement_reflns_used    913
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.4575
_cell_measurement_theta_min      2.6305
_cell_volume                     1549.7(7)
_computing_cell_refinement       'Bruker saintplus (Bruker 1999)'
_computing_data_collection       'Bruker SMART (Bruker 2001)'
_computing_data_reduction        'Bruker saintplus (Bruker 1999)'
_computing_molecular_graphics    'ORTEP (Johnson 1976), Accelrys (2004)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2000)'
_computing_structure_solution    'SHELXL (Sheldrick, 2000)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       '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  0.0510
_diffrn_reflns_av_sigmaI/netI    0.0690
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17980
_diffrn_reflns_theta_full        28.10
_diffrn_reflns_theta_max         28.10
_diffrn_reflns_theta_min         1.31
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.676
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelapiped
_exptl_crystal_F_000             764
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.243
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.118
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.011(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         7278
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0656P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1302
_reflns_number_gt                5476
_reflns_number_total             7278
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jo900376b_si_002.cif
_cod_data_source_block           5-(1R,3S)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

2020-09-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C15 H19 Br N O5'
_cod_original_formula_weight         373.22
_cod_original_formula_moiety         'C13 H17 Br N O2, (C4 H4 O6)0.5'
_cod_original_formula_units_Z            4
_cod_original_sg_symbol_H-M      P21
_cod_database_code               4024600
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.17842(3) 0.02936(9) 0.43957(3) 0.04810(17) Uani 1 1 d . . .
O1 O -0.10261(18) 0.6063(5) 0.88589(19) 0.0324(7) Uani 1 1 d . . .
O2 O -0.18346(19) 0.4488(5) 0.76397(19) 0.0372(7) Uani 1 1 d . . .
N1 N 0.0129(2) 0.2917(6) 0.9274(2) 0.0277(7) Uani 1 1 d . . .
H1A H 0.0373 0.4195 0.9402 0.042 Uiso 1 1 calc R . .
H1B H 0.0550 0.1950 0.9325 0.042 Uiso 1 1 calc R . .
H1C H -0.0178 0.2603 0.9634 0.042 Uiso 1 1 calc R . .
C1 C 0.1336(3) 0.0560(9) 0.5357(3) 0.0366(11) Uani 1 1 d . . .
C2 C 0.1579(3) -0.0859(10) 0.6019(3) 0.0479(13) Uani 1 1 d . . .
H2 H 0.1972 -0.1951 0.6016 0.057 Uiso 1 1 calc R . .
C3 C 0.1227(3) -0.0635(10) 0.6694(3) 0.0441(12) Uani 1 1 d . . .
H3 H 0.1379 -0.1616 0.7143 0.053 Uiso 1 1 calc R . .
C4 C 0.0658(3) 0.0995(8) 0.6727(3) 0.0292(10) Uani 1 1 d . . .
C5 C 0.0433(3) 0.2394(9) 0.6046(3) 0.0422(12) Uani 1 1 d . . .
H5 H 0.0046 0.3500 0.6050 0.051 Uiso 1 1 calc R . .
C6 C 0.0768(3) 0.2201(10) 0.5354(3) 0.0454(13) Uani 1 1 d . . .
H6 H 0.0611 0.3161 0.4898 0.054 Uiso 1 1 calc R . .
C7 C 0.0290(3) 0.1122(8) 0.7485(3) 0.0290(9) Uani 1 1 d . . .
H7 H 0.0730 0.0516 0.7990 0.035 Uiso 1 1 d R . .
C8 C 0.0061(3) 0.3352(7) 0.7728(3) 0.0279(8) Uani 1 1 d . . .
H8A H -0.0291 0.4117 0.7223 0.034 Uiso 1 1 calc R . .
H8B H 0.0590 0.4163 0.8001 0.034 Uiso 1 1 calc R . .
C9 C -0.0472(2) 0.2922(7) 0.8366(2) 0.0264(8) Uani 1 1 d . . .
C10 C -0.0870(3) 0.0674(7) 0.8126(3) 0.0307(10) Uani 1 1 d . . .
H10A H -0.0657 -0.0291 0.8610 0.037 Uiso 1 1 calc R . .
H10B H -0.1509 0.0729 0.7968 0.037 Uiso 1 1 calc R . .
C11 C -0.0574(3) -0.0059(7) 0.7364(3) 0.0334(10) Uani 1 1 d . . .
H11A H -0.1004 0.0322 0.6821 0.040 Uiso 1 1 calc R . .
H11B H -0.0484 -0.1585 0.7379 0.040 Uiso 1 1 calc R . .
C12 C -0.1136(3) 0.4669(7) 0.8338(2) 0.0281(9) Uani 1 1 d . . .
C13 C -0.2499(3) 0.6112(9) 0.7538(3) 0.0420(12) Uani 1 1 d . . .
H13A H -0.2725 0.6081 0.8024 0.063 Uiso 1 1 calc R . .
H13B H -0.2971 0.5856 0.7018 0.063 Uiso 1 1 calc R . .
H13C H -0.2243 0.7479 0.7505 0.063 Uiso 1 1 calc R . .
Br2 Br 0.32571(3) 1.43741(9) 1.56839(3) 0.05081(18) Uani 1 1 d . . .
O3 O 0.59937(17) 1.9168(5) 1.10254(17) 0.0302(6) Uani 1 1 d . . .
O4 O 0.66956(18) 1.7748(5) 1.23056(19) 0.0361(7) Uani 1 1 d . . .
N2 N 0.4694(2) 1.6286(6) 1.06692(19) 0.0243(7) Uani 1 1 d . . .
H2A H 0.4442 1.7561 1.0568 0.036 Uiso 1 1 calc R . .
H2B H 0.4281 1.5301 1.0626 0.036 Uiso 1 1 calc R . .
H2C H 0.4978 1.6024 1.0284 0.036 Uiso 1 1 calc R . .
C14 C 0.3680(3) 1.4375(9) 1.4708(3) 0.0372(10) Uani 1 1 d . . .
C15 C 0.3318(3) 1.5763(9) 1.4041(3) 0.0439(13) Uani 1 1 d . . .
H15 H 0.2868 1.6681 1.4066 0.053 Uiso 1 1 calc R . .
C16 C 0.3634(3) 1.5779(8) 1.3328(3) 0.0375(11) Uani 1 1 d . . .
H16 H 0.3379 1.6689 1.2870 0.045 Uiso 1 1 calc R . .
C17 C 0.4314(3) 1.4477(8) 1.3289(2) 0.0279(9) Uani 1 1 d . . .
C18 C 0.4662(3) 1.3112(9) 1.3970(3) 0.0421(12) Uani 1 1 d . . .
H18 H 0.5121 1.2211 1.3955 0.051 Uiso 1 1 calc R . .
C19 C 0.4341(3) 1.3050(10) 1.4690(3) 0.0456(13) Uani 1 1 d . . .
H19 H 0.4579 1.2114 1.5144 0.055 Uiso 1 1 calc R . .
C20 C 0.4620(3) 1.4463(8) 1.2499(2) 0.0285(9) Uani 1 1 d . . .
H20 H 0.4149 1.3859 1.2020 0.034 Uiso 1 1 d R . .
C21 C 0.4843(3) 1.6690(7) 1.2229(3) 0.0266(9) Uani 1 1 d . . .
H21A H 0.5219 1.7459 1.2720 0.032 Uiso 1 1 calc R . .
H21B H 0.4311 1.7510 1.1977 0.032 Uiso 1 1 calc R . .
C22 C 0.5330(2) 1.6239(7) 1.1554(2) 0.0239(8) Uani 1 1 d . . .
C23 C 0.5716(3) 1.3963(7) 1.1763(3) 0.0293(10) Uani 1 1 d . . .
H23A H 0.5462 1.3008 1.1283 0.035 Uiso 1 1 calc R . .
H23B H 0.6352 1.3978 1.1880 0.035 Uiso 1 1 calc R . .
C24 C 0.5469(3) 1.3275(8) 1.2560(3) 0.0363(10) Uani 1 1 d . . .
H24A H 0.5376 1.1752 1.2558 0.044 Uiso 1 1 calc R . .
H24B H 0.5928 1.3659 1.3084 0.044 Uiso 1 1 calc R . .
C25 C 0.6033(2) 1.7908(7) 1.1578(2) 0.0259(8) Uani 1 1 d . . .
C26 C 0.7403(3) 1.9247(10) 1.2384(3) 0.0424(11) Uani 1 1 d . . .
H26A H 0.7676 1.8978 1.1941 0.064 Uiso 1 1 calc R . .
H26B H 0.7832 1.9095 1.2941 0.064 Uiso 1 1 calc R . .
H26C H 0.7170 2.0666 1.2323 0.064 Uiso 1 1 calc R . .
O5 O 0.33558(18) 1.3098(5) 1.05201(18) 0.0301(7) Uani 1 1 d . . .
O6 O 0.41274(17) 1.0384(5) 1.02424(19) 0.0318(6) Uani 1 1 d . . .
O7 O 0.18503(17) 1.1567(5) 0.9686(2) 0.0310(7) Uani 1 1 d . . .
H7A H 0.1505 1.0853 0.9857 0.046 Uiso 1 1 calc R . .
O8 O 0.27017(18) 0.7908(5) 1.08466(17) 0.0323(7) Uani 1 1 d . . .
H8 H 0.2829 0.9094 1.1056 0.048 Uiso 1 1 calc R . .
O9 O 0.11674(18) 0.6424(5) 1.00074(19) 0.0337(7) Uani 1 1 d . . .
O10 O 0.1298(2) 0.7188(5) 0.8704(2) 0.0415(8) Uani 1 1 d . . .
C27 C 0.3429(2) 1.1340(7) 1.0192(2) 0.0261(8) Uani 1 1 d . . .
C28 C 0.2567(2) 1.0293(7) 0.9652(2) 0.0259(8) Uani 1 1 d . . .
H28 H 0.2574 1.0258 0.9051 0.031 Uiso 1 1 d R . .
C29 C 0.2488(2) 0.8033(6) 0.9930(2) 0.0262(9) Uani 1 1 d . . .
H29 H 0.2911 0.7157 0.9750 0.031 Uiso 1 1 d R . .
C30 C 0.1571(3) 0.7164(6) 0.9502(3) 0.0263(9) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O2 C13 115.5(4) . . ?
C2 C1 C6 121.9(4) . . ?
C2 C1 Br1 120.1(4) . . ?
C6 C1 Br1 118.1(4) . . ?
C1 C2 C3 118.3(5) . . ?
C2 C3 C4 122.3(5) . . ?
C5 C4 C3 117.5(4) . . ?
C5 C4 C7 123.3(4) . . ?
C3 C4 C7 119.2(4) . . ?
C4 C5 C6 121.7(5) . . ?
C1 C6 C5 118.4(5) . . ?
C4 C7 C11 115.0(3) . . ?
C4 C7 C8 115.9(4) . . ?
C11 C7 C8 101.8(3) . . ?
C7 C8 C9 103.5(3) . . ?
N1 C9 C12 105.3(3) . . ?
N1 C9 C8 110.1(3) . . ?
C12 C9 C8 111.7(3) . . ?
N1 C9 C10 109.7(3) . . ?
C12 C9 C10 115.2(3) . . ?
C8 C9 C10 104.8(3) . . ?
C11 C10 C9 106.1(3) . . ?
C10 C11 C7 103.6(3) . . ?
O1 C12 O2 125.0(4) . . ?
O1 C12 C9 123.9(4) . . ?
O2 C12 C9 111.0(3) . . ?
C25 O4 C26 114.7(3) . . ?
C19 C14 C15 121.5(4) . . ?
C19 C14 Br2 119.4(4) . . ?
C15 C14 Br2 119.1(4) . . ?
C14 C15 C16 119.2(5) . . ?
C17 C16 C15 121.3(4) . . ?
C16 C17 C18 117.8(4) . . ?
C16 C17 C20 120.3(4) . . ?
C18 C17 C20 121.8(4) . . ?
C17 C18 C19 121.6(4) . . ?
C14 C19 C18 118.6(5) . . ?
C17 C20 C24 117.1(3) . . ?
C17 C20 C21 113.5(4) . . ?
C24 C20 C21 101.0(3) . . ?
C20 C21 C22 104.0(3) . . ?
N2 C22 C25 106.9(3) . . ?
N2 C22 C21 109.9(3) . . ?
C25 C22 C21 112.0(3) . . ?
N2 C22 C23 109.7(3) . . ?
C25 C22 C23 113.0(3) . . ?
C21 C22 C23 105.3(3) . . ?
C24 C23 C22 105.1(3) . . ?
C20 C24 C23 104.8(3) . . ?
O3 C25 O4 124.8(4) . . ?
O3 C25 C22 124.7(3) . . ?
O4 C25 C22 110.5(3) . . ?
C27 O5 H2B 119.5 . . ?
C30 O9 H1A 108.3 . . ?
O6 C27 O5 126.7(4) . . ?
O6 C27 C28 117.1(4) . . ?
O5 C27 C28 116.2(4) . . ?
O7 C28 C29 112.6(3) . . ?
O7 C28 C27 109.1(3) . . ?
C29 C28 C27 111.9(3) . . ?
O8 C29 C28 110.5(3) . . ?
O8 C29 C30 110.7(3) . . ?
C28 C29 C30 110.9(3) . . ?
O10 C30 O9 126.5(4) . . ?
O10 C30 C29 117.6(4) . . ?
O9 C30 C29 115.9(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.908(4) . ?
O1 C12 1.194(5) . ?
O2 C12 1.332(5) . ?
O2 C13 1.443(6) . ?
N1 C9 1.497(5) . ?
C1 C2 1.361(7) . ?
C1 C6 1.370(7) . ?
C2 C3 1.379(6) . ?
C3 C4 1.379(7) . ?
C4 C5 1.374(6) . ?
C4 C7 1.515(5) . ?
C5 C6 1.386(6) . ?
C7 C11 1.523(6) . ?
C7 C8 1.531(6) . ?
C8 C9 1.546(5) . ?
C9 C12 1.516(6) . ?
C9 C10 1.551(6) . ?
C10 C11 1.522(6) . ?
Br2 C14 1.899(4) . ?
O3 C25 1.185(5) . ?
O4 C25 1.330(5) . ?
O4 C26 1.444(6) . ?
N2 C22 1.489(5) . ?
C14 C19 1.348(7) . ?
C14 C15 1.375(7) . ?
C15 C16 1.393(6) . ?
C16 C17 1.374(6) . ?
C17 C18 1.378(6) . ?
C17 C20 1.502(5) . ?
C18 C19 1.410(6) . ?
C20 C24 1.520(6) . ?
C20 C21 1.541(6) . ?
C21 C22 1.545(5) . ?
C22 C25 1.526(6) . ?
C22 C23 1.555(6) . ?
C23 C24 1.525(5) . ?
O5 C27 1.248(5) . ?
O5 H2B 1.9910 . ?
O6 C27 1.244(5) . ?
O7 C28 1.408(5) . ?
O8 C29 1.425(4) . ?
O9 C30 1.272(5) . ?
O9 H1A 1.9448 . ?
O10 C30 1.237(5) . ?
C27 C28 1.537(5) . ?
C28 C29 1.509(6) . ?
C29 C30 1.518(5) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7A O1 0.82 2.43 3.042(4) 132.5 2_557
N2 H2C O3 0.89 2.51 2.956(4) 111.6 2_647
N2 H2C O6 0.89 1.91 2.773(4) 163.1 2_657
N2 H2B O5 0.89 1.99 2.881(5) 179.6 .
N2 H2A O6 0.89 1.88 2.751(5) 166.4 1_565
N1 H1C O9 0.89 1.98 2.818(4) 156.8 2_547
N1 H1B O7 0.89 1.99 2.749(4) 142.9 1_545
N1 H1A O9 0.89 1.94 2.799(5) 160.3 .
