####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_hy1ccd
_audit_block_doi                 10.5517/cc85qbg
_database_code_depnum_ccdc_archive 'CCDC 243825'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/jo049716t 2004
_audit_update_record             
;
2004-07-06 deposited with the CCDC.	2022-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H15 N O2'
_chemical_formula_weight         205.25

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.3047(18)
_cell_length_b                   6.3689(9)
_cell_length_c                   13.238(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.223(2)
_cell_angle_gamma                90.00
_cell_volume                     1031.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6901
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0582
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2303
_reflns_number_gt                1189
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1057P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2303
_refine_ls_number_parameters     174
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1780
_refine_ls_wR_factor_gt          0.1509
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_restrained_S_all      0.931
_refine_ls_shift/su_max          0.095
_refine_ls_shift/su_mean         0.005

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
O1 O 0.40613(6) 0.06727(11) 0.09111(6) 0.0643(2) Uani 1 1 d . A .
O2 O 0.53580(6) 0.68437(12) 0.26514(7) 0.0648(2) Uani 1 1 d . A .
N1 N 0.56547(7) 0.22366(13) 0.06011(7) 0.0514(3) Uani 1 1 d . A .
H1 H 0.5738 0.1273 0.0150 0.062 Uiso 1 1 calc R . .
C1 C 0.64413(8) 0.37454(15) 0.07543(8) 0.0458(3) Uani 1 1 d D . .
C2 C 0.74071(14) 0.3492(4) 0.01363(17) 0.0588(7) Uani 0.5878(15) 1 d PD A 1
H2A H 0.7862 0.2314 0.0405 0.071 Uiso 0.5878(15) 1 calc PR A 1
H2B H 0.7139 0.3178 -0.0572 0.071 Uiso 0.5878(15) 1 calc PR A 1
C3 C 0.80838(17) 0.5469(3) 0.01794(16) 0.0588(6) Uani 0.5878(15) 1 d PD A 1
H3A H 0.8791 0.5159 -0.0063 0.071 Uiso 0.5878(15) 1 calc PR A 1
H3B H 0.7712 0.6517 -0.0277 0.071 Uiso 0.5878(15) 1 calc PR A 1
C4 C 0.82742(16) 0.6373(3) 0.12319(17) 0.0606(7) Uani 0.5878(15) 1 d PD A 1
H4A H 0.8732 0.7630 0.1219 0.073 Uiso 0.5878(15) 1 calc PR A 1
H4B H 0.8670 0.5347 0.1685 0.073 Uiso 0.5878(15) 1 calc PR A 1
C5 C 0.72184(15) 0.6943(3) 0.16463(16) 0.0481(6) Uani 0.5878(15) 1 d PD A 1
H5A H 0.7361 0.7147 0.2383 0.058 Uiso 0.5878(15) 1 calc PR A 1
H5B H 0.6951 0.8278 0.1345 0.058 Uiso 0.5878(15) 1 calc PR A 1
C2' C 0.7407(3) 0.3512(4) 0.0194(3) 0.0565(10) Uani 0.4122(15) 1 d PD A 2
H2'1 H 0.7190 0.3779 -0.0529 0.068 Uiso 0.4122(15) 1 calc PR A 2
H2'2 H 0.7669 0.2060 0.0262 0.068 Uiso 0.4122(15) 1 calc PR A 2
C3' C 0.8321(3) 0.4964(5) 0.0561(3) 0.0647(10) Uani 0.4122(15) 1 d PD A 2
H3'1 H 0.8841 0.5025 0.0050 0.078 Uiso 0.4122(15) 1 calc PR A 2
H3'2 H 0.8708 0.4396 0.1188 0.078 Uiso 0.4122(15) 1 calc PR A 2
C4' C 0.7928(2) 0.7198(4) 0.0765(3) 0.0643(10) Uani 0.4122(15) 1 d PD A 2
H4'1 H 0.7563 0.7795 0.0135 0.077 Uiso 0.4122(15) 1 calc PR A 2
H4'2 H 0.8559 0.8085 0.0990 0.077 Uiso 0.4122(15) 1 calc PR A 2
C5' C 0.7121(3) 0.7182(6) 0.1595(3) 0.0733(13) Uani 0.4122(15) 1 d PD A 2
H5'1 H 0.7534 0.7096 0.2270 0.088 Uiso 0.4122(15) 1 calc PR A 2
H5'2 H 0.6697 0.8487 0.1559 0.088 Uiso 0.4122(15) 1 calc PR A 2
C6 C 0.63510(8) 0.53115(15) 0.14347(8) 0.0457(3) Uani 1 1 d D A .
C7 C 0.54054(9) 0.52485(15) 0.19723(9) 0.0461(3) Uani 1 1 d . . .
C8 C 0.43131(10) 0.71216(19) 0.30268(11) 0.0742(4) Uani 1 1 d . . .
H8A H 0.3799 0.7732 0.2490 0.089 Uiso 1 1 calc R A .
H8B H 0.4391 0.8107 0.3599 0.089 Uiso 1 1 calc R . .
C9 C 0.38603(11) 0.50893(18) 0.33674(10) 0.0645(4) Uani 1 1 d . A .
H9A H 0.3164 0.5342 0.3643 0.077 Uiso 1 1 calc R . .
H9B H 0.4370 0.4466 0.3905 0.077 Uiso 1 1 calc R . .
C10 C 0.36874(9) 0.36047(17) 0.24766(9) 0.0549(3) Uani 1 1 d . . .
H10A H 0.3615 0.2167 0.2725 0.066 Uiso 1 1 calc R A .
H10B H 0.3009 0.3972 0.2056 0.066 Uiso 1 1 calc R . .
C11 C 0.46330(8) 0.37170(15) 0.18443(8) 0.0462(3) Uani 1 1 d . A .
C12 C 0.47422(9) 0.21291(16) 0.11065(9) 0.0489(3) Uani 1 1 d . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1 C12 1.2579(13) . ?
O2 C7 1.3620(13) . ?
O2 C8 1.4388(15) . ?
N1 C1 1.3634(13) . ?
N1 C12 1.3696(14) . ?
C1 C6 1.3565(15) . ?
C1 C2' 1.474(3) . ?
C1 C2 1.523(2) . ?
C2 C3 1.507(3) . ?
C3 C4 1.502(3) . ?
C4 C5 1.508(3) . ?
C5 C6 1.494(2) . ?
C2' C3' 1.496(4) . ?
C3' C4' 1.536(4) . ?
C4' C5' 1.560(5) . ?
C5' C6 1.523(4) . ?
C6 C7 1.4288(16) . ?
C7 C11 1.3596(14) . ?
C8 C9 1.4978(17) . ?
C9 C10 1.5085(17) . ?
C10 C11 1.5070(16) . ?
C11 C12 1.4224(15) . ?

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
C7 O2 C8 115.06(9) . . ?
C1 N1 C12 124.67(9) . . ?
C6 C1 N1 120.60(10) . . ?
C6 C1 C2' 122.45(14) . . ?
N1 C1 C2' 116.85(13) . . ?
C6 C1 C2 124.01(12) . . ?
N1 C1 C2 115.36(11) . . ?
C2' C1 C2 2.33(16) . . ?
C3 C2 C1 110.58(17) . . ?
C4 C3 C2 112.67(18) . . ?
C3 C4 C5 112.07(17) . . ?
C6 C5 C4 112.96(14) . . ?
C1 C2' C3' 113.2(2) . . ?
C2' C3' C4' 112.9(2) . . ?
C3' C4' C5' 110.8(3) . . ?
C6 C5' C4' 109.9(3) . . ?
C1 C6 C7 116.09(9) . . ?
C1 C6 C5 121.85(12) . . ?
C7 C6 C5 121.99(11) . . ?
C1 C6 C5' 124.99(18) . . ?
C7 C6 C5' 118.72(18) . . ?
C5 C6 C5' 7.54(17) . . ?
C11 C7 O2 122.55(10) . . ?
C11 C7 C6 123.65(10) . . ?
O2 C7 C6 113.78(9) . . ?
O2 C8 C9 111.91(10) . . ?
C8 C9 C10 109.38(11) . . ?
C11 C10 C9 110.64(9) . . ?
C7 C11 C12 118.61(10) . . ?
C7 C11 C10 122.43(10) . . ?
C12 C11 C10 118.93(9) . . ?
O1 C12 N1 119.96(10) . . ?
O1 C12 C11 123.72(11) . . ?
N1 C12 C11 116.32(9) . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.046
