# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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. 
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#######################################################################

data_hele69
_database_code_depnum_ccdc_archive 'CCDC 1533016'
_audit_update_record             
;
2017-02-15 deposited with the CCDC.
2017-04-07 downloaded from the CCDC.
;
_audit_creation_date             2016-09-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H11 N O2'
_chemical_formula_sum            'C10 H11 N O2'
_chemical_formula_weight         177.20
_chemical_absolute_configuration .
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   14.32966(13)
_cell_length_b                   8.77119(8)
_cell_length_c                   14.61018(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1836.33(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9997
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.766
_cell_measurement_theta_min      5.043
_shelx_estimated_absorpt_T_max   0.891
_shelx_estimated_absorpt_T_min   0.867
_exptl_absorpt_coefficient_mu    0.735
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.6892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0678 before and 0.0349 after correction.
The Ratio of minimum to maximum transmission is 0.9147.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Smart diffractometer equipped with an APEX II CCD Detector,
an Incoatec IMuS source and a Quazar MX mirror. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 180.0 degree
scan in 180 frames over three different parts of the reciprocal space
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23996
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.961
_diffrn_reflns_theta_min         5.915
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Microfocus Source'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_reflns_Friedel_coverage         0.855
_reflns_Friedel_fraction_full    0.926
_reflns_Friedel_fraction_max     0.922
_reflns_number_gt                3412
_reflns_number_total             3449
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1548 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3449
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0279
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0479P)²+0.2421P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0742
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C24(H24), C25(H25)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C28(H28), C29(H29), C30(H30),
 C31(H31), C32(H32)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.29899(8) 0.72563(14) 0.33498(9) 0.0245(3) Uani 1 1 d . . . . .
O2 O 0.41800(8) 0.60173(15) 0.40147(9) 0.0265(3) Uani 1 1 d . . . . .
N3 N 0.26473(10) 0.54616(17) 0.43560(11) 0.0235(3) Uani 1 1 d . . . . .
H3 H 0.2768(15) 0.495(3) 0.4820(18) 0.030(6) Uiso 1 1 d . . . . .
C2 C 0.33377(12) 0.62076(19) 0.39303(12) 0.0216(3) Uani 1 1 d . . . . .
C4 C 0.17412(11) 0.61581(19) 0.41933(12) 0.0202(3) Uani 1 1 d . . . . .
H4 H 0.1572 0.6825 0.4723 0.024 Uiso 1 1 calc R . . . .
C5 C 0.19712(11) 0.71625(19) 0.33498(12) 0.0201(3) Uani 1 1 d . . . . .
H5 H 0.1752 0.6647 0.2779 0.024 Uiso 1 1 calc R . . . .
C6 C 0.15783(12) 0.87581(19) 0.33959(14) 0.0253(4) Uani 1 1 d . . . . .
H6A H 0.1787 0.9252 0.3962 0.038 Uiso 1 1 calc GR . . . .
H6B H 0.0895 0.8712 0.3388 0.038 Uiso 1 1 calc GR . . . .
H6C H 0.1798 0.9347 0.2868 0.038 Uiso 1 1 calc GR . . . .
C7 C 0.09661(11) 0.5021(2) 0.40235(11) 0.0199(3) Uani 1 1 d . . . . .
C8 C 0.11385(12) 0.3599(2) 0.36387(13) 0.0261(4) Uani 1 1 d . . . . .
H8 H 0.1758 0.3321 0.3478 0.031 Uiso 1 1 calc R . . . .
C9 C 0.04107(13) 0.2580(2) 0.34867(14) 0.0307(4) Uani 1 1 d . . . . .
H9 H 0.0536 0.1609 0.3227 0.037 Uiso 1 1 calc R . . . .
C10 C -0.04974(13) 0.2977(2) 0.37133(14) 0.0296(4) Uani 1 1 d . . . . .
H10 H -0.0993 0.2275 0.3618 0.036 Uiso 1 1 calc R . . . .
C11 C -0.06766(12) 0.4399(2) 0.40789(14) 0.0304(4) Uani 1 1 d . . . . .
H11 H -0.1299 0.4684 0.4221 0.036 Uiso 1 1 calc R . . . .
C12 C 0.00510(12) 0.5418(2) 0.42402(14) 0.0255(4) Uani 1 1 d . . . . .
H12 H -0.0078 0.6389 0.4499 0.031 Uiso 1 1 calc R . . . .
O21 O 0.44521(8) 0.26229(14) 0.65872(8) 0.0227(3) Uani 1 1 d . . . . .
O22 O 0.32565(8) 0.38010(14) 0.59002(9) 0.0269(3) Uani 1 1 d . . . . .
N23 N 0.47815(10) 0.45413(16) 0.56583(11) 0.0227(3) Uani 1 1 d . . . . .
H23 H 0.4657(15) 0.500(3) 0.517(2) 0.034(6) Uiso 1 1 d . . . . .
C22 C 0.40964(12) 0.36827(18) 0.60214(12) 0.0212(3) Uani 1 1 d . . . . .
C24 C 0.56983(11) 0.38957(18) 0.58442(12) 0.0193(3) Uani 1 1 d . . . . .
H24 H 0.5903 0.3266 0.5310 0.023 Uiso 1 1 calc R . . . .
C25 C 0.54613(10) 0.28393(18) 0.66597(12) 0.0190(3) Uani 1 1 d . . . . .
H25 H 0.5613 0.3367 0.7248 0.023 Uiso 1 1 calc R . . . .
C26 C 0.59286(12) 0.13010(19) 0.66372(14) 0.0242(4) Uani 1 1 d . . . . .
H26A H 0.5731 0.0703 0.7170 0.036 Uiso 1 1 calc GR . . . .
H26B H 0.6607 0.1435 0.6652 0.036 Uiso 1 1 calc GR . . . .
H26C H 0.5752 0.0764 0.6075 0.036 Uiso 1 1 calc GR . . . .
C27 C 0.64431(11) 0.50730(19) 0.60633(11) 0.0196(3) Uani 1 1 d . . . . .
C28 C 0.62259(12) 0.6477(2) 0.64451(13) 0.0252(4) Uani 1 1 d . . . . .
H28 H 0.5594 0.6725 0.6575 0.030 Uiso 1 1 calc R . . . .
C29 C 0.69284(13) 0.7525(2) 0.66390(14) 0.0292(4) Uani 1 1 d . . . . .
H29 H 0.6773 0.8489 0.6893 0.035 Uiso 1 1 calc R . . . .
C30 C 0.78513(13) 0.7168(2) 0.64628(13) 0.0285(4) Uani 1 1 d . . . . .
H30 H 0.8329 0.7889 0.6589 0.034 Uiso 1 1 calc R . . . .
C31 C 0.80754(12) 0.5759(2) 0.61032(16) 0.0318(4) Uani 1 1 d . . . . .
H31 H 0.8710 0.5500 0.5996 0.038 Uiso 1 1 calc R . . . .
C32 C 0.73735(12) 0.4717(2) 0.58970(13) 0.0264(4) Uani 1 1 d . . . . .
H32 H 0.7531 0.3755 0.5641 0.032 Uiso 1 1 calc R . . . .


_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 C2 1.347(2) . ?
O1 C5 1.4621(18) . ?
O2 C2 1.225(2) . ?
N3 H3 0.83(3) . ?
N3 C2 1.339(2) . ?
N3 C4 1.454(2) . ?
C4 H4 1.0000 . ?
C4 C5 1.550(2) . ?
C4 C7 1.513(2) . ?
C5 H5 1.0000 . ?
C5 C6 1.510(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.390(3) . ?
C7 C12 1.393(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.391(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.387(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.381(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.393(2) . ?
C12 H12 0.9500 . ?
O21 C22 1.344(2) . ?
O21 C25 1.4625(17) . ?
O22 C22 1.221(2) . ?
N23 H23 0.84(3) . ?
N23 C22 1.346(2) . ?
N23 C24 1.456(2) . ?
C24 H24 1.0000 . ?
C24 C25 1.547(2) . ?
C24 C27 1.519(2) . ?
C25 H25 1.0000 . ?
C25 C26 1.507(2) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.387(2) . ?
C27 C32 1.391(2) . ?
C28 H28 0.9500 . ?
C28 C29 1.393(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.383(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.381(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.392(3) . ?
C32 H32 0.9500 . ?

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
C2 O1 C5 109.33(12) . . ?
C2 N3 H3 119.3(15) . . ?
C2 N3 C4 112.23(14) . . ?
C4 N3 H3 123.1(16) . . ?
O2 C2 O1 121.41(15) . . ?
O2 C2 N3 127.93(16) . . ?
N3 C2 O1 110.66(14) . . ?
N3 C4 H4 109.6 . . ?
N3 C4 C5 100.30(12) . . ?
N3 C4 C7 113.91(14) . . ?
C5 C4 H4 109.6 . . ?
C7 C4 H4 109.6 . . ?
C7 C4 C5 113.59(14) . . ?
O1 C5 C4 104.14(12) . . ?
O1 C5 H5 109.8 . . ?
O1 C5 C6 108.67(13) . . ?
C4 C5 H5 109.8 . . ?
C6 C5 C4 114.33(15) . . ?
C6 C5 H5 109.8 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C4 121.81(15) . . ?
C8 C7 C12 118.90(16) . . ?
C12 C7 C4 119.28(15) . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.51(16) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.25(18) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.57(17) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.38(17) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 C11 120.37(17) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C22 O21 C25 109.25(12) . . ?
C22 N23 H23 116.8(15) . . ?
C22 N23 C24 111.52(13) . . ?
C24 N23 H23 122.5(16) . . ?
O21 C22 N23 110.65(14) . . ?
O22 C22 O21 121.44(15) . . ?
O22 C22 N23 127.89(16) . . ?
N23 C24 H24 109.5 . . ?
N23 C24 C25 100.29(12) . . ?
N23 C24 C27 114.13(13) . . ?
C25 C24 H24 109.5 . . ?
C27 C24 H24 109.5 . . ?
C27 C24 C25 113.52(14) . . ?
O21 C25 C24 103.83(12) . . ?
O21 C25 H25 109.7 . . ?
O21 C25 C26 108.77(13) . . ?
C24 C25 H25 109.7 . . ?
C26 C25 C24 114.97(14) . . ?
C26 C25 H25 109.7 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 C24 122.04(15) . . ?
C28 C27 C32 118.99(16) . . ?
C32 C27 C24 118.95(15) . . ?
C27 C28 H28 119.8 . . ?
C27 C28 C29 120.38(16) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 119.9 . . ?
C30 C29 C28 120.25(17) . . ?
C30 C29 H29 119.9 . . ?
C29 C30 H30 120.1 . . ?
C31 C30 C29 119.73(17) . . ?
C31 C30 H30 120.1 . . ?
C30 C31 H31 119.9 . . ?
C30 C31 C32 120.13(17) . . ?
C32 C31 H31 119.9 . . ?
C27 C32 C31 120.50(17) . . ?
C27 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?

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
N3 H3 O22 0.83(3) 2.00(3) 2.8238(19) 171(2) .
N23 H23 O2 0.84(3) 2.02(3) 2.861(2) 172(2) .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C4 C5 O1 -17.22(17) . . . . ?
N3 C4 C5 C6 -135.66(14) . . . . ?
N3 C4 C7 C8 -28.5(2) . . . . ?
N3 C4 C7 C12 152.89(16) . . . . ?
C2 O1 C5 C4 13.19(18) . . . . ?
C2 O1 C5 C6 135.44(16) . . . . ?
C2 N3 C4 C5 16.89(18) . . . . ?
C2 N3 C4 C7 138.59(15) . . . . ?
C4 N3 C2 O1 -9.8(2) . . . . ?
C4 N3 C2 O2 170.87(18) . . . . ?
C4 C7 C8 C9 -179.70(17) . . . . ?
C4 C7 C12 C11 179.15(17) . . . . ?
C5 O1 C2 O2 176.46(15) . . . . ?
C5 O1 C2 N3 -2.9(2) . . . . ?
C5 C4 C7 C8 85.57(19) . . . . ?
C5 C4 C7 C12 -93.09(18) . . . . ?
C7 C4 C5 O1 -139.15(14) . . . . ?
C7 C4 C5 C6 102.42(17) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C8 C7 C12 C11 0.4(3) . . . . ?
C8 C9 C10 C11 0.9(3) . . . . ?
C9 C10 C11 C12 -1.5(3) . . . . ?
C10 C11 C12 C7 0.8(3) . . . . ?
C12 C7 C8 C9 -1.0(3) . . . . ?
N23 C24 C25 O21 19.98(15) . . . . ?
N23 C24 C25 C26 138.67(14) . . . . ?
N23 C24 C27 C28 27.0(2) . . . . ?
N23 C24 C27 C32 -154.66(16) . . . . ?
C22 O21 C25 C24 -15.52(16) . . . . ?
C22 O21 C25 C26 -138.38(15) . . . . ?
C22 N23 C24 C25 -19.25(18) . . . . ?
C22 N23 C24 C27 -140.97(16) . . . . ?
C24 N23 C22 O21 10.8(2) . . . . ?
C24 N23 C22 O22 -170.53(17) . . . . ?
C24 C27 C28 C29 179.80(17) . . . . ?
C24 C27 C32 C31 -178.96(18) . . . . ?
C25 O21 C22 O22 -174.94(16) . . . . ?
C25 O21 C22 N23 3.82(19) . . . . ?
C25 C24 C27 C28 -87.14(19) . . . . ?
C25 C24 C27 C32 91.24(19) . . . . ?
C27 C24 C25 O21 142.13(13) . . . . ?
C27 C24 C25 C26 -99.18(17) . . . . ?
C27 C28 C29 C30 -0.8(3) . . . . ?
C28 C27 C32 C31 -0.5(3) . . . . ?
C28 C29 C30 C31 -0.8(3) . . . . ?
C29 C30 C31 C32 1.6(3) . . . . ?
C30 C31 C32 C27 -1.0(3) . . . . ?
C32 C27 C28 C29 1.4(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_hele67
_database_code_depnum_ccdc_archive 'CCDC 1533015'
_audit_update_record             
;
2017-02-15 deposited with the CCDC.
2017-04-07 downloaded from the CCDC.
;
_audit_creation_date             2016-07-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H19 N O2'
_chemical_formula_sum            'C11 H19 N O2'
_chemical_formula_weight         197.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0150 0.0070 '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 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0410 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.0400(4)
_cell_length_b                   6.0462(2)
_cell_length_c                   12.0358(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.0384(11)
_cell_angle_gamma                90
_cell_volume                     1092.93(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9856
_cell_measurement_temperature    150
_cell_measurement_theta_max      60.632
_cell_measurement_theta_min      2.561
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.884
_exptl_absorpt_coefficient_mu    0.419
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1459 before and 0.0511 after correction.
The Ratio of minimum to maximum transmission is 0.8626.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18135
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.601
_diffrn_reflns_theta_min         2.560
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2300
_reflns_number_total             2496
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       0.074(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2496
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0705P)²+0.3481P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1223
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C9(H9A,H9B)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.62300(5) 0.07173(13) 0.53539(6) 0.0190(2) Uani 1 1 d . . . . .
O2 O 0.54734(6) -0.05352(14) 0.67910(7) 0.0237(2) Uani 1 1 d . . . . .
C2 C 0.57029(7) 0.10223(19) 0.62300(8) 0.0169(3) Uani 1 1 d . . . . .
N3 N 0.55113(6) 0.31824(16) 0.63309(8) 0.0172(2) Uani 1 1 d . . . . .
H3 H 0.5263(11) 0.366(3) 0.6910(13) 0.028(4) Uiso 1 1 d . . . . .
C4 C 0.61027(7) 0.45042(18) 0.56676(8) 0.0154(2) Uani 1 1 d . . . . .
H4 H 0.5790 0.5848 0.5360 0.019 Uiso 1 1 calc R . . . .
C5 C 0.62484(7) 0.28234(18) 0.47524(8) 0.0177(3) Uani 1 1 d . . . . .
H5 H 0.5730 0.2878 0.4197 0.021 Uiso 1 1 calc R . . . .
C6 C 0.70998(8) 0.3079(2) 0.41462(9) 0.0220(3) Uani 1 1 d . . . . .
H6A H 0.7003 0.4203 0.3555 0.026 Uiso 1 1 calc R . . . .
H6B H 0.7232 0.1658 0.3781 0.026 Uiso 1 1 calc R . . . .
C7 C 0.79095(7) 0.37554(19) 0.48895(9) 0.0186(3) Uani 1 1 d . . . . .
H7A H 0.8412 0.4098 0.4419 0.022 Uiso 1 1 calc R . . . .
H7B H 0.8090 0.2503 0.5381 0.022 Uiso 1 1 calc R . . . .
C8 C 0.77135(6) 0.57780(17) 0.56048(8) 0.0145(2) Uani 1 1 d . . . . .
H8 H 0.7484 0.6971 0.5091 0.017 Uiso 1 1 calc R . . . .
C9 C 0.69553(6) 0.51398(18) 0.63457(8) 0.0149(2) Uani 1 1 d . . . . .
H9A H 0.7148 0.3878 0.6824 0.018 Uiso 1 1 calc R . . . .
H9B H 0.6827 0.6401 0.6837 0.018 Uiso 1 1 calc R . . . .
C10 C 0.85506(7) 0.67098(18) 0.62644(9) 0.0179(3) Uani 1 1 d . . . . .
C11 C 0.82771(8) 0.8528(2) 0.70670(10) 0.0240(3) Uani 1 1 d . . . . .
H11A H 0.7860 0.9545 0.6676 0.036 Uiso 1 1 calc GR . . . .
H11B H 0.8807 0.9346 0.7341 0.036 Uiso 1 1 calc GR . . . .
H11C H 0.7989 0.7856 0.7696 0.036 Uiso 1 1 calc GR . . . .
C12 C 0.90551(8) 0.4912(2) 0.69409(10) 0.0271(3) Uani 1 1 d . . . . .
H12A H 0.8648 0.4182 0.7434 0.041 Uiso 1 1 calc GR . . . .
H12B H 0.9547 0.5588 0.7387 0.041 Uiso 1 1 calc GR . . . .
H12C H 0.9292 0.3819 0.6433 0.041 Uiso 1 1 calc GR . . . .
C13 C 0.91801(8) 0.7739(2) 0.54420(11) 0.0274(3) Uani 1 1 d . . . . .
H13A H 0.9371 0.6599 0.4928 0.041 Uiso 1 1 calc GR . . . .
H13B H 0.9702 0.8357 0.5854 0.041 Uiso 1 1 calc GR . . . .
H13C H 0.8868 0.8918 0.5021 0.041 Uiso 1 1 calc GR . . . .


_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 C2 1.3649(12) . ?
O1 C5 1.4657(13) . ?
O2 C2 1.2192(13) . ?
C2 N3 1.3444(15) . ?
N3 H3 0.859(16) . ?
N3 C4 1.4638(13) . ?
C4 H4 1.0000 . ?
C4 C5 1.5230(14) . ?
C4 C9 1.5320(14) . ?
C5 H5 1.0000 . ?
C5 C6 1.5149(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5282(15) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5332(14) . ?
C8 H8 1.0000 . ?
C8 C9 1.5336(13) . ?
C8 C10 1.5579(14) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5340(15) . ?
C10 C12 1.5342(16) . ?
C10 C13 1.5371(15) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
C2 O1 C5 106.93(8) . . ?
O2 C2 O1 121.10(10) . . ?
O2 C2 N3 129.20(10) . . ?
N3 C2 O1 109.70(9) . . ?
C2 N3 H3 120.4(11) . . ?
C2 N3 C4 109.99(8) . . ?
C4 N3 H3 124.2(11) . . ?
N3 C4 H4 111.0 . . ?
N3 C4 C5 98.34(8) . . ?
N3 C4 C9 111.23(8) . . ?
C5 C4 H4 111.0 . . ?
C5 C4 C9 113.84(8) . . ?
C9 C4 H4 111.0 . . ?
O1 C5 C4 102.43(8) . . ?
O1 C5 H5 108.9 . . ?
O1 C5 C6 111.41(9) . . ?
C4 C5 H5 108.9 . . ?
C6 C5 C4 115.98(9) . . ?
C6 C5 H5 108.9 . . ?
C5 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
C5 C6 C7 114.40(8) . . ?
H6A C6 H6B 107.6 . . ?
C7 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C6 C7 C8 111.80(9) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C7 C8 H8 107.3 . . ?
C7 C8 C9 107.27(8) . . ?
C7 C8 C10 113.60(8) . . ?
C9 C8 H8 107.3 . . ?
C9 C8 C10 113.61(8) . . ?
C10 C8 H8 107.3 . . ?
C4 C9 C8 112.37(8) . . ?
C4 C9 H9A 109.1 . . ?
C4 C9 H9B 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C8 110.09(9) . . ?
C11 C10 C12 108.37(9) . . ?
C11 C10 C13 108.07(9) . . ?
C12 C10 C8 112.20(9) . . ?
C12 C10 C13 108.93(10) . . ?
C13 C10 C8 109.09(9) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
N3 H3 O2 0.859(16) 2.022(17) 2.8738(12) 171.3(15) 2_656

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 N3 C4 -14.27(12) . . . . ?
O1 C5 C6 C7 -78.31(12) . . . . ?
O2 C2 N3 C4 165.71(11) . . . . ?
C2 O1 C5 C4 28.21(10) . . . . ?
C2 O1 C5 C6 152.84(9) . . . . ?
C2 N3 C4 C5 30.29(11) . . . . ?
C2 N3 C4 C9 -89.39(10) . . . . ?
N3 C4 C5 O1 -33.80(9) . . . . ?
N3 C4 C5 C6 -155.35(9) . . . . ?
N3 C4 C9 C8 159.75(9) . . . . ?
C4 C5 C6 C7 38.33(14) . . . . ?
C5 O1 C2 O2 170.30(10) . . . . ?
C5 O1 C2 N3 -9.71(11) . . . . ?
C5 C4 C9 C8 49.77(12) . . . . ?
C5 C6 C7 C8 -50.73(13) . . . . ?
C6 C7 C8 C9 60.89(11) . . . . ?
C6 C7 C8 C10 -172.70(9) . . . . ?
C7 C8 C9 C4 -60.73(11) . . . . ?
C7 C8 C10 C11 -172.76(9) . . . . ?
C7 C8 C10 C12 -51.98(12) . . . . ?
C7 C8 C10 C13 68.82(11) . . . . ?
C9 C4 C5 O1 83.90(10) . . . . ?
C9 C4 C5 C6 -37.65(13) . . . . ?
C9 C8 C10 C11 -49.77(12) . . . . ?
C9 C8 C10 C12 71.01(12) . . . . ?
C9 C8 C10 C13 -168.19(9) . . . . ?
C10 C8 C9 C4 172.87(9) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
