#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:39:52 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180310 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/24/7152412.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_7152412
loop_
_publ_author_name
'Ortiz, Adrian'
'Young, Ian S.'
'Sawyer, James R.'
'Hsiao, Yi'
'Singh, Amarjit'
'Sugiyama, Masano'
'Corbett, R. Michael'
'Chau, Melissa'
'Shi, Zhongping'
'Conlon, David A.'
_publ_section_title
;
 Synthetic approaches to a chiral 4-amino-3-hydroxy piperidine with
 pharmaceutical relevance.
;
_journal_issue                   27
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5253
_journal_page_last               5257
_journal_paper_doi               10.1039/c2ob25411e
_journal_volume                  10
_journal_year                    2012
_chemical_formula_sum            'C20 H30 Cl2 N2 O2'
_chemical_formula_weight         401.36
_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                   5.7182(3)
_cell_length_b                   12.0175(7)
_cell_length_c                   30.1828(17)
_cell_measurement_reflns_used    6947
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      54.98
_cell_measurement_theta_min      4.70
_cell_volume                     2074.1(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            12961
_diffrn_reflns_theta_full        55.23
_diffrn_reflns_theta_max         55.23
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    2.941
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.044(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         2579
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0531P)²+0.5707P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.0979
_reflns_number_gt                2418
_reflns_number_total             2579
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25411e.txt
_cod_data_source_block           p212121
_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.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P2(1)2(1)2(1) '
_cod_database_code               7152412
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
C1 C 0.5508(6) 0.6021(3) 0.10380(10) 0.0326(8) Uani 1 1 d .
C2 C 0.3445(6) 0.5563(3) 0.08759(11) 0.0370(8) Uani 1 1 d .
H2 H 0.2369 0.5247 0.1075 0.044 Uiso 1 1 calc R
C3 C 0.2949(7) 0.5564(3) 0.04294(12) 0.0422(9) Uani 1 1 d .
H3 H 0.1554 0.5240 0.0327 0.051 Uiso 1 1 calc R
C4 C 0.4483(7) 0.6035(3) 0.01325(12) 0.0453(9) Uani 1 1 d .
H4 H 0.4137 0.6040 -0.0172 0.054 Uiso 1 1 calc R
C5 C 0.6535(7) 0.6502(3) 0.02866(12) 0.0463(10) Uani 1 1 d .
H5 H 0.7596 0.6822 0.0086 0.056 Uiso 1 1 calc R
C6 C 0.7042(6) 0.6503(3) 0.07376(11) 0.0406(9) Uani 1 1 d .
H6 H 0.8434 0.6831 0.0840 0.049 Uiso 1 1 calc R
C7 C 0.6193(6) 0.5995(3) 0.15169(10) 0.0359(8) Uani 1 1 d .
H7A H 0.6806 0.5254 0.1588 0.043 Uiso 1 1 calc R
H7B H 0.7453 0.6534 0.1566 0.043 Uiso 1 1 calc R
C8 C 0.5006(5) 0.6549(3) 0.22825(10) 0.0265(7) Uani 1 1 d .
H8 H 0.6047 0.7206 0.2265 0.032 Uiso 1 1 calc R
C9 C 0.2909(6) 0.6840(3) 0.25681(10) 0.0287(7) Uani 1 1 d .
H9 H 0.1869 0.6184 0.2591 0.034 Uiso 1 1 calc R
C10 C 0.3717(6) 0.7174(3) 0.30285(10) 0.0295(7) Uani 1 1 d .
H10A H 0.4709 0.7837 0.3009 0.035 Uiso 1 1 calc R
H10B H 0.2356 0.7358 0.3212 0.035 Uiso 1 1 calc R
C11 C 0.7099(5) 0.5910(3) 0.29602(10) 0.0325(7) Uani 1 1 d .
H11A H 0.7890 0.5276 0.3099 0.039 Uiso 1 1 calc R
H11B H 0.8217 0.6527 0.2944 0.039 Uiso 1 1 calc R
C12 C 0.6342(6) 0.5595(3) 0.24987(10) 0.0301(7) Uani 1 1 d .
H12A H 0.5341 0.4933 0.2512 0.036 Uiso 1 1 calc R
H12B H 0.7720 0.5413 0.2320 0.036 Uiso 1 1 calc R
C13 C 0.5925(6) 0.6523(3) 0.36985(11) 0.0394(8) Uani 1 1 d .
H13A H 0.7112 0.7109 0.3677 0.047 Uiso 1 1 calc R
H13B H 0.6674 0.5862 0.3825 0.047 Uiso 1 1 calc R
C14 C 0.3996(6) 0.6908(3) 0.40076(11) 0.0379(8) Uani 1 1 d .
C15 C 0.3781(8) 0.8023(3) 0.41089(13) 0.0526(10) Uani 1 1 d .
H15 H 0.4836 0.8536 0.3985 0.063 Uiso 1 1 calc R
C16 C 0.2052(8) 0.8394(3) 0.43874(14) 0.0637(12) Uani 1 1 d .
H16 H 0.1930 0.9156 0.4453 0.076 Uiso 1 1 calc R
C17 C 0.0492(8) 0.7651(3) 0.45717(13) 0.0559(11) Uani 1 1 d .
H17 H -0.0709 0.7906 0.4759 0.067 Uiso 1 1 calc R
C18 C 0.0706(7) 0.6538(3) 0.44802(12) 0.0511(10) Uani 1 1 d .
H18 H -0.0334 0.6028 0.4610 0.061 Uiso 1 1 calc R
C19 C 0.2438(7) 0.6158(3) 0.41985(12) 0.0482(10) Uani 1 1 d .
H19 H 0.2564 0.5394 0.4136 0.058 Uiso 1 1 calc R
Cl1 Cl 0.11878(13) 0.40559(7) 0.18849(3) 0.0365(2) Uani 1 1 d .
Cl2 Cl 0.24090(16) 0.40943(8) 0.32913(3) 0.0534(3) Uani 1 1 d .
N1 N 0.4220(4) 0.62537(19) 0.18251(8) 0.0271(6) Uani 1 1 d .
H1A H 0.3256 0.5653 0.1840 0.032 Uiso 1 1 calc R
H1B H 0.3381 0.6831 0.1712 0.032 Uiso 1 1 calc R
N2 N 0.5056(4) 0.6250(2) 0.32397(8) 0.0289(6) Uani 1 1 d D
H2N H 0.407(5) 0.5623(17) 0.3282(10) 0.035 Uiso 1 1 d D
O1 O 0.1691(4) 0.7720(2) 0.23607(7) 0.0481(7) Uani 1 1 d .
H1 H 0.0808 0.8021 0.2543 0.072 Uiso 1 1 calc R
O1S O 0.1691(5) 0.7807(2) 0.13587(8) 0.0622(8) Uani 1 1 d .
H1S H 0.0774 0.8174 0.1514 0.093 Uiso 1 1 calc R
C1S C 0.2362(8) 0.8430(4) 0.09969(14) 0.0642(12) Uani 1 1 d .
H1S1 H 0.1170 0.8981 0.0933 0.096 Uiso 1 1 calc R
H1S2 H 0.2558 0.7946 0.0742 0.096 Uiso 1 1 calc R
H1S3 H 0.3830 0.8801 0.1061 0.096 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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 118.1(3)
C6 C1 C7 118.3(3)
C2 C1 C7 123.6(3)
C3 C2 C1 121.3(3)
C4 C3 C2 120.4(3)
C3 C4 C5 119.3(3)
C4 C5 C6 120.4(3)
C1 C6 C5 120.5(3)
N1 C7 C1 113.5(3)
N1 C8 C9 110.0(2)
N1 C8 C12 111.6(2)
C9 C8 C12 109.0(3)
O1 C9 C8 108.1(2)
O1 C9 C10 111.0(3)
C8 C9 C10 109.9(3)
N2 C10 C9 110.5(2)
N2 C11 C12 111.4(2)
C11 C12 C8 110.5(3)
N2 C13 C14 113.1(3)
C15 C14 C19 118.7(3)
C15 C14 C13 119.8(3)
C19 C14 C13 121.5(3)
C16 C15 C14 121.0(4)
C15 C16 C17 120.2(4)
C18 C17 C16 119.5(4)
C17 C18 C19 120.7(4)
C18 C19 C14 119.9(3)
C7 N1 C8 113.4(2)
C10 N2 C11 111.2(2)
C10 N2 C13 113.5(2)
C11 N2 C13 108.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.388(5)
C1 C2 1.391(5)
C1 C7 1.498(5)
C2 C3 1.377(5)
C3 C4 1.376(5)
C4 C5 1.381(5)
C5 C6 1.392(5)
C7 N1 1.495(4)
C8 N1 1.495(4)
C8 C9 1.517(4)
C8 C12 1.524(4)
C9 O1 1.412(4)
C9 C10 1.518(4)
C10 N2 1.492(4)
C11 N2 1.498(4)
C11 C12 1.507(5)
C13 N2 1.508(4)
C13 C14 1.517(5)
C14 C15 1.380(5)
C14 C19 1.392(5)
C15 C16 1.372(6)
C16 C17 1.379(6)
C17 C18 1.372(6)
C18 C19 1.383(5)
O1S C1S 1.379(5)
