#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:47:55 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179674 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/26/4512632.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_4512632
loop_
_publ_author_name
'Tsang, Min Ying'
'Di Salvo, Florencia'
'Teixidor, Francesc'
'Viñas, Clara'
'Planas, José Giner'
'Choquesillo-Lazarte, Duane'
'Vanthuyne, Nicolas'
_publ_section_title
;
 Is Molecular Chirality Connected to Supramolecular Chirality? The
 Particular Case of Chiral 2-Pyridyl Alcohols
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              935
_journal_paper_doi               10.1021/cg501748x
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C12 H11 N O'
_chemical_formula_sum            'C12 H11 N O'
_chemical_formula_weight         185.22
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 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                   7.4141(9)
_cell_length_b                   14.2828(15)
_cell_length_c                   9.2478(9)
_cell_measurement_reflns_used    1356
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8717
_cell_measurement_theta_min      3.5146
_cell_volume                     979.29(18)
_computing_cell_refinement
;
'Mon Dec 17 14:40:12 2012'
;
_computing_data_collection
;
'Mon Dec 17 14:40:12 2012'
;
_computing_data_reduction
;
'Mon Dec 17 14:40:12 2012'
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1158
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω 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  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6504
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.94
_diffrn_reflns_theta_min         3.80
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
       CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.110
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2063
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0459
_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)+(0.0308P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0969
_reflns_number_gt                1450
_reflns_number_total             2063
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg501748x_si_002.cif
_cod_data_source_block           Rac-5a
_cod_depositor_comments
'Adding full bibliography for 4512623--4512632.cif.'
_cod_database_code               4512632
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, 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
O1 O 0.9469(3) 0.53486(15) 0.17820(17) 0.0684(6) Uani 1 1 d
N1 N 0.9379(3) 0.62574(15) 0.53116(19) 0.0558(6) Uani 1 1 d
C1 C 0.8947(3) 0.61972(16) 0.3913(2) 0.0443(5) Uani 1 1 d
C6 C 0.9051(3) 0.52273(17) 0.3261(2) 0.0484(6) Uani 1 1 d
C8 C 0.7178(4) 0.39522(17) 0.4426(3) 0.0570(6) Uani 1 1 d
C12 C 0.5766(3) 0.49530(19) 0.2717(3) 0.0580(7) Uani 1 1 d
C7 C 0.7300(3) 0.46955(15) 0.3474(2) 0.0434(5) Uani 1 1 d
C5 C 0.8442(4) 0.69600(18) 0.3108(3) 0.0577(6) Uani 1 1 d
C2 C 0.9310(4) 0.7115(2) 0.5913(3) 0.0718(9) Uani 1 1 d
C10 C 0.4066(4) 0.3752(2) 0.3858(3) 0.0678(8) Uani 1 1 d
C9 C 0.5566(4) 0.3487(2) 0.4615(3) 0.0671(8) Uani 1 1 d
C11 C 0.4153(4) 0.4488(2) 0.2916(3) 0.0679(8) Uani 1 1 d
C4 C 0.8356(4) 0.7825(2) 0.3749(4) 0.0743(8) Uani 1 1 d
C3 C 0.8820(5) 0.7901(2) 0.5173(4) 0.0809(9) Uani 1 1 d
H5 H 0.812(3) 0.6872(15) 0.208(3) 0.059(7) Uiso 1 1 d
H6 H 1.007(3) 0.4863(16) 0.376(2) 0.049(6) Uiso 1 1 d
H3 H 0.880(4) 0.853(2) 0.563(3) 0.087(9) Uiso 1 1 d
H12 H 0.581(4) 0.551(2) 0.205(3) 0.079(8) Uiso 1 1 d
H11 H 0.315(4) 0.469(2) 0.235(3) 0.092(10) Uiso 1 1 d
H4 H 0.799(4) 0.837(2) 0.316(3) 0.089(10) Uiso 1 1 d
H2 H 0.966(4) 0.7093(17) 0.700(3) 0.080(8) Uiso 1 1 d
H9 H 0.562(4) 0.290(2) 0.528(3) 0.087(9) Uiso 1 1 d
H8 H 0.836(4) 0.3790(16) 0.495(2) 0.062(7) Uiso 1 1 d
H1 H 0.966(4) 0.482(2) 0.138(3) 0.083(11) Uiso 1 1 d
H10 H 0.286(4) 0.341(2) 0.398(3) 0.094(10) Uiso 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 O1 H1 110(2)
C1 N1 C2 116.7(2)
N1 C1 C5 122.7(2)
N1 C1 C6 115.6(2)
C5 C1 C6 121.7(2)
O1 C6 C1 106.5(2)
O1 C6 C7 111.99(18)
C1 C6 C7 111.29(18)
O1 C6 H6 109.7(11)
C1 C6 H6 108.9(12)
C7 C6 H6 108.4(13)
C9 C8 C7 120.5(2)
C9 C8 H8 124.8(13)
C7 C8 H8 114.6(13)
C11 C12 C7 121.1(3)
C11 C12 H12 119.3(15)
C7 C12 H12 119.5(16)
C8 C7 C12 118.1(2)
C8 C7 C6 121.6(2)
C12 C7 C6 120.3(2)
C1 C5 C4 119.6(3)
C1 C5 H5 119.1(14)
C4 C5 H5 121.3(14)
N1 C2 C3 123.5(3)
N1 C2 H2 111.2(14)
C3 C2 H2 125.3(14)
C11 C10 C9 120.0(3)
C11 C10 H10 118.5(16)
C9 C10 H10 121.5(16)
C10 C9 C8 120.4(3)
C10 C9 H9 123.9(16)
C8 C9 H9 115.4(16)
C10 C11 C12 119.8(3)
C10 C11 H11 123.4(19)
C12 C11 H11 116.8(19)
C3 C4 C5 118.4(3)
C3 C4 H4 122.7(17)
C5 C4 H4 118.9(17)
C2 C3 C4 119.1(3)
C2 C3 H3 122.3(17)
C4 C3 H3 118.6(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C6 1.413(3)
O1 H1 0.85(3)
N1 C1 1.335(3)
N1 C2 1.347(4)
C1 C5 1.372(3)
C1 C6 1.513(3)
C6 C7 1.517(3)
C6 H6 1.03(2)
C8 C9 1.378(4)
C8 C7 1.382(3)
C8 H8 1.03(3)
C12 C11 1.380(4)
C12 C7 1.385(3)
C12 H12 1.01(3)
C5 C4 1.372(4)
C5 H5 0.98(2)
C2 C3 1.363(5)
C2 H2 1.04(3)
C10 C11 1.366(4)
C10 C9 1.368(4)
C10 H10 1.02(3)
C9 H9 1.03(3)
C11 H11 0.95(3)
C4 C3 1.365(4)
C4 H4 0.99(3)
C3 H3 1.00(3)
