# Electronic Supplementary Material (ESI) for RSC Advances.
# 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. 
# 
#######################################################################

data_hjl_22
_database_code_depnum_ccdc_archive 'CCDC 1522361'
_audit_update_record             
;
2016-12-13 deposited with the CCDC.
2017-02-27 downloaded from the CCDC.
;
_audit_creation_date             2015-05-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H24 Cl N2 O'
_chemical_formula_sum            'C16 H24 Cl N2 O'
_chemical_formula_weight         295.82
_chemical_absolute_configuration ad
_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 0.0033 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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   8.4983(5)
_cell_length_b                   8.3756(5)
_cell_length_c                   10.7054(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.311(6)
_cell_angle_gamma                90.00
_cell_volume                     731.32(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    734
_cell_measurement_temperature    295.35(10)
_cell_measurement_theta_max      28.0980
_cell_measurement_theta_min      3.6420
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             318
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.27
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2457
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.49
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.35(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -8.00   91.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   77.0000   90.0000 66

#__ type_ start__ end____ width___ exp.time_
  2 omega   -7.00   75.50   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   77.0000 -150.0000 55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0497401000
_diffrn_orient_matrix_UB_12      0.0133126000
_diffrn_orient_matrix_UB_13      0.0644148000
_diffrn_orient_matrix_UB_21      -0.0669068000
_diffrn_orient_matrix_UB_22      0.0368756000
_diffrn_orient_matrix_UB_23      0.0159741000
_diffrn_orient_matrix_UB_31      -0.0239775000
_diffrn_orient_matrix_UB_32      -0.0751087000
_diffrn_orient_matrix_UB_33      0.0193478000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1660
_reflns_number_total             1998
_reflns_odcompleteness_completeness 94.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.09(11)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1998
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0492
_refine_ls_restrained_S_all      1.032
_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)+(0.0678P)²+0.0115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1326
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 N2(H2), C2(H2A), C9(H9), C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B),
 C8(H8A,H8B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl -0.20785(11) 0.63836(15) 0.06867(9) 0.0506(3) Uani 1 d . . .
O1 O -0.0792(4) 0.5469(4) -0.2807(3) 0.0635(10) Uani 1 d . . .
N1 N 0.1081(3) 0.6631(4) 0.1728(3) 0.0337(8) Uani 1 d . . .
N2 N 0.4222(4) 0.4987(4) 0.4438(3) 0.0346(7) Uani 1 d . . .
H2 H 0.4126 0.6062 0.4317 0.042 Uiso 1 calc . . R
C1 C 0.0832(4) 0.6397(6) 0.3023(3) 0.0373(8) Uani 1 d . . .
H1A H -0.0294 0.6641 0.2990 0.045 Uiso 1 calc . . R
H1B H 0.1544 0.7110 0.3646 0.045 Uiso 1 calc . . R
C2 C 0.1220(4) 0.4666(5) 0.3446(4) 0.0344(9) Uani 1 d . . .
H2A H 0.0440 0.3989 0.2821 0.041 Uiso 1 calc . . R
C3 C 0.1008(5) 0.4329(6) 0.4785(4) 0.0478(11) Uani 1 d . . .
H3A H -0.0042 0.4744 0.4824 0.057 Uiso 1 calc . . R
H3B H 0.1007 0.3184 0.4919 0.057 Uiso 1 calc . . R
C4 C 0.2365(5) 0.5082(6) 0.5863(4) 0.0503(11) Uani 1 d . . .
H4A H 0.2259 0.6235 0.5819 0.060 Uiso 1 calc . . R
H4B H 0.2268 0.4736 0.6702 0.060 Uiso 1 calc . . R
C5 C 0.4032(5) 0.4601(6) 0.5723(4) 0.0471(11) Uani 1 d . . .
H5A H 0.4880 0.5143 0.6385 0.057 Uiso 1 calc . . R
H5B H 0.4179 0.3461 0.5871 0.057 Uiso 1 calc . . R
C6 C 0.5867(5) 0.4495(6) 0.4409(4) 0.0459(11) Uani 1 d . . .
H6A H 0.5993 0.3358 0.4584 0.055 Uiso 1 calc . . R
H6B H 0.6674 0.5047 0.5096 0.055 Uiso 1 calc . . R
C7 C 0.6199(5) 0.4841(6) 0.3123(4) 0.0472(11) Uani 1 d . . .
H7A H 0.6211 0.5986 0.2991 0.057 Uiso 1 calc . . R
H7B H 0.7266 0.4422 0.3132 0.057 Uiso 1 calc . . R
C8 C 0.4892(5) 0.4085(5) 0.2017(4) 0.0424(10) Uani 1 d . . .
H8A H 0.4981 0.2932 0.2083 0.051 Uiso 1 calc . . R
H8B H 0.5058 0.4403 0.1193 0.051 Uiso 1 calc . . R
C9 C 0.3197(4) 0.4594(4) 0.2061(3) 0.0326(9) Uani 1 d . . .
H9 H 0.2399 0.3966 0.1406 0.039 Uiso 1 calc . . R
C10 C 0.2952(5) 0.4191(5) 0.3402(4) 0.0334(9) Uani 1 d . . .
H10 H 0.3073 0.3034 0.3534 0.040 Uiso 1 calc . . R
C11 C 0.2810(4) 0.6364(5) 0.1750(3) 0.0314(8) Uani 1 d . . .
H11 H 0.3502 0.6994 0.2468 0.038 Uiso 1 calc . . R
C12 C 0.3075(5) 0.6981(5) 0.0501(4) 0.0441(11) Uani 1 d . . .
H12A H 0.4210 0.6814 0.0514 0.053 Uiso 1 calc . . R
H12B H 0.2859 0.8120 0.0431 0.053 Uiso 1 calc . . R
C13 C 0.1952(5) 0.6133(6) -0.0681(3) 0.0451(12) Uani 1 d . . .
H13A H 0.1983 0.6687 -0.1470 0.054 Uiso 1 calc . . R
H13B H 0.2338 0.5051 -0.0727 0.054 Uiso 1 calc . . R
C14 C 0.0224(5) 0.6095(5) -0.0587(3) 0.0373(10) Uani 1 d . . .
C15 C -0.0070(4) 0.6336(5) 0.0592(3) 0.0342(8) Uani 1 d . . .
C16 C -0.1045(5) 0.5720(5) -0.1748(4) 0.0474(11) Uani 1 d . . .
H16 H -0.2119 0.5664 -0.1699 0.057 Uiso 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
Cl1 C15 1.739(3) . ?
O1 C16 1.230(5) . ?
N1 C1 1.473(4) . ?
N1 C11 1.480(4) . ?
N1 C15 1.352(4) . ?
N2 H2 0.9100 . ?
N2 C5 1.465(5) . ?
N2 C6 1.466(5) . ?
N2 C10 1.473(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.527(6) . ?
C2 H2A 0.9800 . ?
C2 C3 1.520(5) . ?
C2 C10 1.538(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.520(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.520(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.509(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.516(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.515(5) . ?
C9 H9 0.9800 . ?
C9 C10 1.545(5) . ?
C9 C11 1.535(6) . ?
C10 H10 0.9800 . ?
C11 H11 0.9800 . ?
C11 C12 1.509(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.529(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.501(5) . ?
C14 C15 1.369(4) . ?
C14 C16 1.434(5) . ?
C16 H16 0.9300 . ?

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
C1 N1 C11 111.6(3) . . ?
C15 N1 C1 124.3(3) . . ?
C15 N1 C11 116.8(3) . . ?
C5 N2 H2 108.8 . . ?
C5 N2 C6 108.4(3) . . ?
C5 N2 C10 110.9(3) . . ?
C6 N2 H2 108.8 . . ?
C6 N2 C10 111.0(3) . . ?
C10 N2 H2 108.8 . . ?
N1 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
N1 C1 C2 109.2(3) . . ?
H1A C1 H1B 108.3 . . ?
C2 C1 H1A 109.8 . . ?
C2 C1 H1B 109.8 . . ?
C1 C2 H2A 107.4 . . ?
C1 C2 C10 111.4(3) . . ?
C3 C2 C1 112.5(3) . . ?
C3 C2 H2A 107.4 . . ?
C3 C2 C10 110.4(3) . . ?
C10 C2 H2A 107.4 . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 C2 111.9(3) . . ?
C4 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C3 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 C3 110.1(4) . . ?
C5 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
N2 C5 C4 112.7(3) . . ?
N2 C5 H5A 109.1 . . ?
N2 C5 H5B 109.1 . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
N2 C6 H6A 109.0 . . ?
N2 C6 H6B 109.0 . . ?
N2 C6 C7 112.9(3) . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C8 C7 C6 110.4(3) . . ?
C8 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 C9 110.7(3) . . ?
H8A C8 H8B 108.1 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C8 C9 H9 107.5 . . ?
C8 C9 C10 110.1(3) . . ?
C8 C9 C11 114.4(3) . . ?
C10 C9 H9 107.5 . . ?
C11 C9 H9 107.5 . . ?
C11 C9 C10 109.6(3) . . ?
N2 C10 C2 111.4(3) . . ?
N2 C10 C9 109.9(3) . . ?
N2 C10 H10 108.3 . . ?
C2 C10 C9 110.6(3) . . ?
C2 C10 H10 108.3 . . ?
C9 C10 H10 108.3 . . ?
N1 C11 C9 107.5(3) . . ?
N1 C11 H11 107.8 . . ?
N1 C11 C12 109.2(3) . . ?
C9 C11 H11 107.8 . . ?
C12 C11 C9 116.5(3) . . ?
C12 C11 H11 107.8 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C11 C12 C13 111.1(3) . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C12 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C14 C13 C12 110.4(3) . . ?
C14 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
C15 C14 C13 119.6(3) . . ?
C15 C14 C16 123.0(4) . . ?
C16 C14 C13 117.3(3) . . ?
N1 C15 Cl1 114.7(2) . . ?
N1 C15 C14 125.7(3) . . ?
C14 C15 Cl1 119.6(3) . . ?
O1 C16 C14 123.6(4) . . ?
O1 C16 H16 118.2 . . ?
C14 C16 H16 118.2 . . ?

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
N1 C1 C2 C3 179.5(3) . . . . ?
N1 C1 C2 C10 54.8(4) . . . . ?
N1 C11 C12 C13 -59.4(5) . . . . ?
N2 C6 C7 C8 -55.0(5) . . . . ?
C1 N1 C11 C9 65.7(4) . . . . ?
C1 N1 C11 C12 -167.0(4) . . . . ?
C1 N1 C15 Cl1 23.3(6) . . . . ?
C1 N1 C15 C14 -160.2(4) . . . . ?
C1 C2 C3 C4 -72.5(5) . . . . ?
C1 C2 C10 N2 70.6(4) . . . . ?
C1 C2 C10 C9 -51.9(4) . . . . ?
C2 C3 C4 C5 -52.3(5) . . . . ?
C3 C2 C10 N2 -55.2(4) . . . . ?
C3 C2 C10 C9 -177.7(3) . . . . ?
C3 C4 C5 N2 55.3(5) . . . . ?
C5 N2 C6 C7 -179.9(4) . . . . ?
C5 N2 C10 C2 58.0(4) . . . . ?
C5 N2 C10 C9 -179.1(3) . . . . ?
C6 N2 C5 C4 179.4(3) . . . . ?
C6 N2 C10 C2 178.5(3) . . . . ?
C6 N2 C10 C9 -58.6(4) . . . . ?
C6 C7 C8 C9 53.7(5) . . . . ?
C7 C8 C9 C10 -55.7(5) . . . . ?
C7 C8 C9 C11 68.3(4) . . . . ?
C8 C9 C10 N2 58.0(4) . . . . ?
C8 C9 C10 C2 -178.7(3) . . . . ?
C8 C9 C11 N1 175.5(3) . . . . ?
C8 C9 C11 C12 52.6(4) . . . . ?
C9 C11 C12 C13 62.5(4) . . . . ?
C10 N2 C5 C4 -58.6(5) . . . . ?
C10 N2 C6 C7 58.1(5) . . . . ?
C10 C2 C3 C4 52.7(5) . . . . ?
C10 C9 C11 N1 -60.3(3) . . . . ?
C10 C9 C11 C12 176.9(3) . . . . ?
C11 N1 C1 C2 -62.9(4) . . . . ?
C11 N1 C15 Cl1 170.9(3) . . . . ?
C11 N1 C15 C14 -12.5(6) . . . . ?
C11 C9 C10 N2 -68.7(4) . . . . ?
C11 C9 C10 C2 54.7(4) . . . . ?
C11 C12 C13 C14 47.9(5) . . . . ?
C12 C13 C14 C15 -18.7(6) . . . . ?
C12 C13 C14 C16 164.4(4) . . . . ?
C13 C14 C15 Cl1 177.0(3) . . . . ?
C13 C14 C15 N1 0.6(7) . . . . ?
C13 C14 C16 O1 -1.7(6) . . . . ?
C15 N1 C1 C2 86.3(4) . . . . ?
C15 N1 C11 C9 -85.9(4) . . . . ?
C15 N1 C11 C12 41.4(5) . . . . ?
C15 C14 C16 O1 -178.5(4) . . . . ?
C16 C14 C15 Cl1 -6.3(6) . . . . ?
C16 C14 C15 N1 177.3(4) . . . . ?

_olex2_date_sample_data_collection 2015-05-07
_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_hjl_40
_database_code_depnum_ccdc_archive 'CCDC 1524887'
_audit_update_record             
;
2016-12-29 deposited with the CCDC.
2017-02-27 downloaded from the CCDC.
;
_audit_creation_date             2015-11-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H27 N3 O4'
_chemical_formula_sum            'C22 H27 N3 O4'
_chemical_formula_weight         397.46
_chemical_absolute_configuration unk
_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 0.0033 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'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.8606(7)
_cell_length_b                   9.8660(6)
_cell_length_c                   12.1556(16)
_cell_angle_alpha                90
_cell_angle_beta                 108.727(11)
_cell_angle_gamma                90
_cell_volume                     1006.37(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    611
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.2440
_cell_measurement_theta_min      3.9960
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.12764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0876
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3911
_diffrn_reflns_point_group_measured_fraction_full 0.719
_diffrn_reflns_point_group_measured_fraction_max 0.712
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.015
_diffrn_reflns_theta_min         3.433
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   51.00   81.00   2.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4291  178.0000   90.0000 15

#__ type_ start__ end____ width___ exp.time_
  2 omega   71.00   95.00   2.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4291  178.0000  150.0000 12

#__ type_ start__ end____ width___ exp.time_
  3 omega  -22.00   92.00   2.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4291   19.0000 -120.0000 57

#__ type_ start__ end____ width___ exp.time_
  4 omega  -15.00   35.00   2.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4291  -57.0000   30.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0504352000
_diffrn_orient_matrix_UB_12      -0.0439506000
_diffrn_orient_matrix_UB_13      -0.0420854000
_diffrn_orient_matrix_UB_21      0.0261798000
_diffrn_orient_matrix_UB_22      0.0304851000
_diffrn_orient_matrix_UB_23      -0.0436187000
_diffrn_orient_matrix_UB_31      0.0625348000
_diffrn_orient_matrix_UB_32      -0.0480699000
_diffrn_orient_matrix_UB_33      0.0109414000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.355
_reflns_Friedel_fraction_full    0.414
_reflns_Friedel_fraction_max     0.397
_reflns_number_gt                1582
_reflns_number_total             2814
_reflns_odcompleteness_completeness 98.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 395 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.6(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2814
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0596
_refine_ls_restrained_S_all      1.077
_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)+(0.0260P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1256
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C6(H6), C11(H11), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C9(H9A,H9B), C8(H8A,H8B), C1(H1A,H1B), C7(H7A,H7B), C12(H12A,
 H12B), C5(H5A,H5B), C3(H3A,H3B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C19(H19), C22(H22), C21(H21), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O2 O -0.0205(4) -0.5515(4) -0.1422(4) 0.0604(12) Uani 1 1 d . . . . .
C14 C 0.1333(6) -0.4935(6) 0.0505(5) 0.0422(15) Uani 1 1 d . . . . .
O1 O 0.2165(5) -0.7165(4) 0.0177(4) 0.0626(13) Uani 1 1 d . . . . .
C15 C 0.2526(7) -0.6019(6) 0.0611(5) 0.0504(16) Uani 1 1 d . . . . .
N1 N 0.8003(6) -0.5243(6) 0.3258(4) 0.0579(15) Uani 1 1 d . . . . .
C17 C -0.1629(7) -0.5378(6) -0.2311(5) 0.0493(16) Uani 1 1 d . . . . .
C20 C -0.4339(8) -0.5376(7) -0.4172(6) 0.0623(19) Uani 1 1 d . . . . .
C16 C 0.0060(7) -0.4751(6) -0.0429(5) 0.0550(18) Uani 1 1 d . . . . .
H16 H -0.0674 -0.4085 -0.0412 0.066 Uiso 1 1 calc R . . . .
N2 N 0.4047(5) -0.5703(4) 0.1250(4) 0.0463(13) Uani 1 1 d . . . . .
C2 C 0.6785(8) -0.6334(6) 0.1357(6) 0.060(2) Uani 1 1 d . . . . .
H2 H 0.6547 -0.6161 0.0525 0.072 Uiso 1 1 calc R . . . .
O4 O -0.5986(7) -0.6256(6) -0.5908(5) 0.105(2) Uani 1 1 d . . . . .
C19 C -0.4288(8) -0.4656(7) -0.3228(7) 0.089(3) Uani 1 1 d . . . . .
H19 H -0.5172 -0.4160 -0.3211 0.106 Uiso 1 1 calc R . . . .
N3 N -0.5826(8) -0.5402(8) -0.5161(6) 0.081(2) Uani 1 1 d . . . . .
C6 C 0.7424(7) -0.5024(7) 0.1997(5) 0.0561(18) Uani 1 1 d . . . . .
H6 H 0.8315 -0.4707 0.1752 0.067 Uiso 1 1 calc R . . . .
C13 C 0.1685(7) -0.3963(6) 0.1485(5) 0.0548(17) Uani 1 1 d . . . . .
H13A H 0.1694 -0.4426 0.2191 0.066 Uiso 1 1 calc R . . . .
H13B H 0.0879 -0.3258 0.1319 0.066 Uiso 1 1 calc R . . . .
C9 C 0.6772(8) -0.2630(7) 0.2312(6) 0.070(2) Uani 1 1 d . . . . .
H9A H 0.5938 -0.1949 0.2147 0.084 Uiso 1 1 calc R . . . .
H9B H 0.7616 -0.2292 0.2039 0.084 Uiso 1 1 calc R . . . .
C11 C 0.4601(6) -0.4433(5) 0.1907(5) 0.0433(15) Uani 1 1 d . . . . .
H11 H 0.4884 -0.4646 0.2736 0.052 Uiso 1 1 calc R . . . .
C22 C -0.1694(8) -0.6068(7) -0.3302(6) 0.0648(19) Uani 1 1 d . . . . .
H22 H -0.0796 -0.6523 -0.3347 0.078 Uiso 1 1 calc R . . . .
C8 C 0.7425(8) -0.2878(7) 0.3620(6) 0.076(2) Uani 1 1 d . . . . .
H8A H 0.7902 -0.2052 0.4012 0.091 Uiso 1 1 calc R . . . .
H8B H 0.6561 -0.3133 0.3906 0.091 Uiso 1 1 calc R . . . .
C21 C -0.3083(9) -0.6094(7) -0.4238(6) 0.072(2) Uani 1 1 d . . . . .
H21 H -0.3147 -0.6597 -0.4898 0.086 Uiso 1 1 calc R . . . .
O3 O -0.6865(8) -0.4586(7) -0.5165(6) 0.139(3) Uani 1 1 d . . . . .
C1 C 0.5243(8) -0.6768(6) 0.1551(6) 0.0606(19) Uani 1 1 d . . . . .
H1A H 0.4827 -0.7565 0.1084 0.073 Uiso 1 1 calc R . . . .
H1B H 0.5463 -0.7013 0.2360 0.073 Uiso 1 1 calc R . . . .
C7 C 0.8653(9) -0.3990(8) 0.3882(6) 0.082(2) Uani 1 1 d . . . . .
H7A H 0.9560 -0.3696 0.3661 0.098 Uiso 1 1 calc R . . . .
H7B H 0.9023 -0.4166 0.4711 0.098 Uiso 1 1 calc R . . . .
C12 C 0.3310(7) -0.3350(6) 0.1629(6) 0.0557(18) Uani 1 1 d . . . . .
H12A H 0.3562 -0.2687 0.2251 0.067 Uiso 1 1 calc R . . . .
H12B H 0.3281 -0.2887 0.0919 0.067 Uiso 1 1 calc R . . . .
C10 C 0.6108(7) -0.3928(6) 0.1681(5) 0.0527(17) Uani 1 1 d . . . . .
H10 H 0.5830 -0.3751 0.0846 0.063 Uiso 1 1 calc R . . . .
C5 C 0.9264(8) -0.6260(8) 0.3560(6) 0.079(2) Uani 1 1 d . . . . .
H5A H 0.9654 -0.6369 0.4397 0.095 Uiso 1 1 calc R . . . .
H5B H 1.0143 -0.5941 0.3316 0.095 Uiso 1 1 calc R . . . .
C3 C 0.8048(9) -0.7458(8) 0.1699(6) 0.081(2) Uani 1 1 d . . . . .
H3A H 0.7574 -0.8308 0.1357 0.097 Uiso 1 1 calc R . . . .
H3B H 0.8905 -0.7244 0.1393 0.097 Uiso 1 1 calc R . . . .
C18 C -0.2897(9) -0.4653(7) -0.2266(6) 0.087(3) Uani 1 1 d . . . . .
H18 H -0.2848 -0.4157 -0.1605 0.105 Uiso 1 1 calc R . . . .
C4 C 0.8720(9) -0.7615(8) 0.3007(7) 0.084(2) Uani 1 1 d . . . . .
H4A H 0.7910 -0.7984 0.3301 0.101 Uiso 1 1 calc R . . . .
H4B H 0.9612 -0.8241 0.3202 0.101 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
O2 C17 1.380(6) . ?
O2 C16 1.377(6) . ?
C14 C15 1.480(8) . ?
C14 C16 1.332(7) . ?
C14 C13 1.482(8) . ?
O1 C15 1.245(7) . ?
C15 N2 1.358(6) . ?
N1 C6 1.468(7) . ?
N1 C7 1.468(8) . ?
N1 C5 1.459(8) . ?
C17 C22 1.368(8) . ?
C17 C18 1.348(8) . ?
C20 C19 1.338(9) . ?
C20 N3 1.471(7) . ?
C20 C21 1.342(9) . ?
C16 H16 0.9300 . ?
N2 C11 1.482(6) . ?
N2 C1 1.454(7) . ?
C2 H2 0.9800 . ?
C2 C6 1.521(8) . ?
C2 C1 1.521(8) . ?
C2 C3 1.535(9) . ?
O4 N3 1.213(7) . ?
C19 H19 0.9300 . ?
C19 C18 1.401(8) . ?
N3 O3 1.222(8) . ?
C6 H6 0.9800 . ?
C6 C10 1.546(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.519(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.527(8) . ?
C9 C10 1.512(9) . ?
C11 H11 0.9800 . ?
C11 C12 1.522(7) . ?
C11 C10 1.530(8) . ?
C22 H22 0.9300 . ?
C22 C21 1.382(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.505(9) . ?
C21 H21 0.9300 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C10 H10 0.9800 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.504(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.516(9) . ?
C18 H18 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?

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
C16 O2 C17 119.2(5) . . ?
C15 C14 C13 116.0(5) . . ?
C16 C14 C15 123.9(6) . . ?
C16 C14 C13 120.0(6) . . ?
O1 C15 C14 122.7(5) . . ?
O1 C15 N2 121.6(5) . . ?
N2 C15 C14 115.7(5) . . ?
C6 N1 C7 111.3(5) . . ?
C5 N1 C6 110.2(5) . . ?
C5 N1 C7 107.9(5) . . ?
C22 C17 O2 114.2(6) . . ?
C18 C17 O2 125.8(6) . . ?
C18 C17 C22 120.0(6) . . ?
C19 C20 N3 119.0(7) . . ?
C19 C20 C21 122.0(6) . . ?
C21 C20 N3 119.0(7) . . ?
O2 C16 H16 118.9 . . ?
C14 C16 O2 122.2(6) . . ?
C14 C16 H16 118.9 . . ?
C15 N2 C11 126.8(5) . . ?
C15 N2 C1 119.2(5) . . ?
C1 N2 C11 112.7(4) . . ?
C6 C2 H2 107.6 . . ?
C6 C2 C1 111.5(5) . . ?
C6 C2 C3 110.9(5) . . ?
C1 C2 H2 107.6 . . ?
C1 C2 C3 111.5(6) . . ?
C3 C2 H2 107.6 . . ?
C20 C19 H19 120.1 . . ?
C20 C19 C18 119.7(7) . . ?
C18 C19 H19 120.1 . . ?
O4 N3 C20 118.9(8) . . ?
O4 N3 O3 123.2(7) . . ?
O3 N3 C20 117.9(8) . . ?
N1 C6 C2 110.9(5) . . ?
N1 C6 H6 108.6 . . ?
N1 C6 C10 110.2(5) . . ?
C2 C6 H6 108.6 . . ?
C2 C6 C10 109.9(5) . . ?
C10 C6 H6 108.6 . . ?
C14 C13 H13A 110.3 . . ?
C14 C13 H13B 110.3 . . ?
C14 C13 C12 107.3(5) . . ?
H13A C13 H13B 108.5 . . ?
C12 C13 H13A 110.3 . . ?
C12 C13 H13B 110.3 . . ?
H9A C9 H9B 108.1 . . ?
C8 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C10 C9 C8 110.3(5) . . ?
N2 C11 H11 107.7 . . ?
N2 C11 C12 112.2(4) . . ?
N2 C11 C10 109.6(4) . . ?
C12 C11 H11 107.7 . . ?
C12 C11 C10 111.6(5) . . ?
C10 C11 H11 107.7 . . ?
C17 C22 H22 119.7 . . ?
C17 C22 C21 120.5(7) . . ?
C21 C22 H22 119.7 . . ?
C9 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C7 C8 C9 110.2(6) . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
C20 C21 C22 118.5(7) . . ?
C20 C21 H21 120.7 . . ?
C22 C21 H21 120.7 . . ?
N2 C1 C2 112.1(5) . . ?
N2 C1 H1A 109.2 . . ?
N2 C1 H1B 109.2 . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
N1 C7 C8 111.5(6) . . ?
N1 C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C13 C12 C11 111.3(5) . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C6 C10 H10 107.5 . . ?
C9 C10 C6 109.1(5) . . ?
C9 C10 C11 113.9(5) . . ?
C9 C10 H10 107.5 . . ?
C11 C10 C6 111.1(5) . . ?
C11 C10 H10 107.5 . . ?
N1 C5 H5A 109.0 . . ?
N1 C5 H5B 109.0 . . ?
N1 C5 C4 112.9(6) . . ?
H5A C5 H5B 107.8 . . ?
C4 C5 H5A 109.0 . . ?
C4 C5 H5B 109.0 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 C2 111.4(6) . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C17 C18 C19 119.1(7) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C5 C4 C3 109.8(7) . . ?
C5 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?

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
O2 C17 C22 C21 175.8(6) . . . . ?
O2 C17 C18 C19 -177.4(7) . . . . ?
C14 C15 N2 C11 4.4(9) . . . . ?
C14 C15 N2 C1 170.3(5) . . . . ?
C14 C13 C12 C11 -60.7(7) . . . . ?
O1 C15 N2 C11 -173.4(5) . . . . ?
O1 C15 N2 C1 -7.5(9) . . . . ?
C15 C14 C16 O2 -4.2(10) . . . . ?
C15 C14 C13 C12 56.2(7) . . . . ?
C15 N2 C11 C12 -10.4(8) . . . . ?
C15 N2 C11 C10 -135.1(6) . . . . ?
C15 N2 C1 C2 134.7(6) . . . . ?
N1 C6 C10 C9 58.3(6) . . . . ?
N1 C6 C10 C11 -68.0(6) . . . . ?
N1 C5 C4 C3 56.6(9) . . . . ?
C17 O2 C16 C14 172.9(6) . . . . ?
C17 C22 C21 C20 3.2(11) . . . . ?
C20 C19 C18 C17 0.1(12) . . . . ?
C16 O2 C17 C22 173.0(5) . . . . ?
C16 O2 C17 C18 -7.3(9) . . . . ?
C16 C14 C15 O1 -35.1(10) . . . . ?
C16 C14 C15 N2 147.1(6) . . . . ?
C16 C14 C13 C12 -119.5(6) . . . . ?
N2 C11 C12 C13 38.6(7) . . . . ?
N2 C11 C10 C6 -56.5(6) . . . . ?
N2 C11 C10 C9 179.8(5) . . . . ?
C2 C6 C10 C9 -179.2(5) . . . . ?
C2 C6 C10 C11 54.4(6) . . . . ?
C2 C3 C4 C5 -51.6(9) . . . . ?
C19 C20 N3 O4 -165.1(7) . . . . ?
C19 C20 N3 O3 12.4(11) . . . . ?
C19 C20 C21 C22 -0.9(11) . . . . ?
N3 C20 C19 C18 178.1(7) . . . . ?
N3 C20 C21 C22 -179.7(6) . . . . ?
C6 N1 C7 C8 58.9(7) . . . . ?
C6 N1 C5 C4 -60.6(8) . . . . ?
C6 C2 C1 N2 54.5(7) . . . . ?
C6 C2 C3 C4 52.0(8) . . . . ?
C13 C14 C15 O1 149.3(6) . . . . ?
C13 C14 C15 N2 -28.5(8) . . . . ?
C13 C14 C16 O2 171.2(5) . . . . ?
C9 C8 C7 N1 -56.4(8) . . . . ?
C11 N2 C1 C2 -57.5(7) . . . . ?
C22 C17 C18 C19 2.2(11) . . . . ?
C8 C9 C10 C6 -56.6(7) . . . . ?
C8 C9 C10 C11 68.2(7) . . . . ?
C21 C20 C19 C18 -0.7(12) . . . . ?
C21 C20 N3 O4 13.7(11) . . . . ?
C21 C20 N3 O3 -168.7(8) . . . . ?
C1 N2 C11 C12 -177.1(5) . . . . ?
C1 N2 C11 C10 58.3(6) . . . . ?
C1 C2 C6 N1 69.5(6) . . . . ?
C1 C2 C6 C10 -52.5(6) . . . . ?
C1 C2 C3 C4 -72.9(8) . . . . ?
C7 N1 C6 C2 178.8(5) . . . . ?
C7 N1 C6 C10 -59.4(7) . . . . ?
C7 N1 C5 C4 177.7(6) . . . . ?
C12 C11 C10 C6 178.5(5) . . . . ?
C12 C11 C10 C9 54.8(7) . . . . ?
C10 C9 C8 C7 56.0(8) . . . . ?
C10 C11 C12 C13 162.1(5) . . . . ?
C5 N1 C6 C2 59.1(7) . . . . ?
C5 N1 C6 C10 -179.0(6) . . . . ?
C5 N1 C7 C8 180.0(6) . . . . ?
C3 C2 C6 N1 -55.4(7) . . . . ?
C3 C2 C6 C10 -177.4(6) . . . . ?
C3 C2 C1 N2 179.0(5) . . . . ?
C18 C17 C22 C21 -3.8(11) . . . . ?

_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_hjl_66
_database_code_depnum_ccdc_archive 'CCDC 1524886'
_audit_update_record             
;
2016-12-29 deposited with the CCDC.
2017-02-27 downloaded from the CCDC.
;
_audit_creation_date             2015-12-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H30 N2 O2, C7 H8 O'
_chemical_formula_sum            'C30 H38 N2 O3'
_chemical_formula_weight         474.62
_chemical_absolute_configuration unk
_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 0.0033 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'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.5122(5)
_cell_length_b                   9.5461(4)
_cell_length_c                   13.5190(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.723(4)
_cell_angle_gamma                90
_cell_volume                     1337.15(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1423
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.4570
_cell_measurement_theta_min      3.8970
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5382
_diffrn_reflns_point_group_measured_fraction_full 0.838
_diffrn_reflns_point_group_measured_fraction_max 0.823
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.344
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -80.00  -42.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  139.0000  137.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega    8.00   80.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4291   57.0000  120.0000 48

#__ type_ start__ end____ width___ exp.time_
  3 omega  -20.00   94.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4291   19.0000 -120.0000 76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0606134000
_diffrn_orient_matrix_UB_12      0.0100830000
_diffrn_orient_matrix_UB_13      0.0154097000
_diffrn_orient_matrix_UB_21      -0.0300451000
_diffrn_orient_matrix_UB_22      0.0054532000
_diffrn_orient_matrix_UB_23      -0.0509092000
_diffrn_orient_matrix_UB_31      -0.0105495000
_diffrn_orient_matrix_UB_32      -0.0734138000
_diffrn_orient_matrix_UB_33      -0.0016462000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.553
_reflns_Friedel_fraction_full    0.657
_reflns_Friedel_fraction_max     0.626
_reflns_number_gt                3010
_reflns_number_total             4345
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 880 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -1.0(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4345
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0608
_refine_ls_restrained_S_all      1.041
_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)+(0.0448P)²+0.1328P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1447
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C18(H18), C19(H19), C21(H21), C22(H22), C25(H25), C26(H26),
 C28(H28), C29(H29)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C30(H30A,H30B,H30C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.0227(4) 0.0828(4) -0.7059(3) 0.0720(11) Uani 1 1 d . . . . .
O2 O 0.0023(3) -0.0593(3) -0.4282(2) 0.0469(8) Uani 1 1 d . . . . .
N1 N -0.2114(3) 0.0020(3) -0.4414(3) 0.0370(9) Uani 1 1 d . . . . .
N2 N -0.4886(4) 0.0218(4) -0.3174(3) 0.0451(10) Uani 1 1 d . . . . .
C1 C -0.1072(4) -0.0023(4) -0.4852(3) 0.0407(11) Uani 1 1 d . . . . .
C2 C -0.1041(5) 0.0408(5) -0.5816(4) 0.0470(12) Uani 1 1 d . . . . .
C3 C -0.2318(5) 0.0837(6) -0.6414(4) 0.0580(13) Uani 1 1 d . . . . .
H3A H -0.2825 0.0015 -0.6644 0.070 Uiso 1 1 calc R . . . .
H3B H -0.2185 0.1376 -0.6997 0.070 Uiso 1 1 calc R . . . .
C4 C -0.3022(5) 0.1723(5) -0.5737(4) 0.0519(13) Uani 1 1 d . . . . .
H4A H -0.2517 0.2554 -0.5527 0.062 Uiso 1 1 calc R . . . .
H4B H -0.3847 0.2022 -0.6112 0.062 Uiso 1 1 calc R . . . .
C5 C -0.3247(4) 0.0907(5) -0.4810(3) 0.0380(10) Uani 1 1 d . . . . .
H5 H -0.3994 0.0292 -0.5005 0.046 Uiso 1 1 calc R . . . .
C6 C -0.3523(4) 0.1860(4) -0.3960(3) 0.0404(11) Uani 1 1 d . . . . .
H6 H -0.2775 0.2478 -0.3780 0.048 Uiso 1 1 calc R . . . .
C7 C -0.3689(4) 0.1042(5) -0.3013(3) 0.0404(11) Uani 1 1 d . . . . .
H7 H -0.3738 0.1718 -0.2475 0.048 Uiso 1 1 calc R . . . .
C8 C -0.2515(4) 0.0096(5) -0.2681(3) 0.0402(11) Uani 1 1 d . . . . .
H8 H -0.1756 0.0697 -0.2495 0.048 Uiso 1 1 calc R . . . .
C9 C -0.2287(5) -0.0828(4) -0.3544(3) 0.0392(11) Uani 1 1 d . . . . .
H9A H -0.1524 -0.1396 -0.3336 0.047 Uiso 1 1 calc R . . . .
H9B H -0.3016 -0.1452 -0.3727 0.047 Uiso 1 1 calc R . . . .
C10 C -0.2677(5) -0.0784(5) -0.1765(3) 0.0512(13) Uani 1 1 d . . . . .
H10A H -0.1987 -0.1470 -0.1639 0.061 Uiso 1 1 calc R . . . .
H10B H -0.2611 -0.0182 -0.1181 0.061 Uiso 1 1 calc R . . . .
C11 C -0.3966(5) -0.1534(5) -0.1919(4) 0.0575(14) Uani 1 1 d . . . . .
H11A H -0.3974 -0.2257 -0.2424 0.069 Uiso 1 1 calc R . . . .
H11B H -0.4088 -0.1980 -0.1297 0.069 Uiso 1 1 calc R . . . .
C12 C -0.5053(5) -0.0520(6) -0.2247(4) 0.0588(15) Uani 1 1 d . . . . .
H12A H -0.5866 -0.1025 -0.2361 0.071 Uiso 1 1 calc R . . . .
H12B H -0.5086 0.0159 -0.1719 0.071 Uiso 1 1 calc R . . . .
C13 C -0.6016(5) 0.1132(6) -0.3468(4) 0.0636(16) Uani 1 1 d . . . . .
H13A H -0.6078 0.1784 -0.2927 0.076 Uiso 1 1 calc R . . . .
H13B H -0.6793 0.0565 -0.3575 0.076 Uiso 1 1 calc R . . . .
C14 C -0.5928(5) 0.1943(6) -0.4413(4) 0.0648(16) Uani 1 1 d . . . . .
H14A H -0.5946 0.1297 -0.4969 0.078 Uiso 1 1 calc R . . . .
H14B H -0.6665 0.2563 -0.4568 0.078 Uiso 1 1 calc R . . . .
C15 C -0.4699(5) 0.2792(5) -0.4287(4) 0.0576(15) Uani 1 1 d . . . . .
H15A H -0.4729 0.3515 -0.3788 0.069 Uiso 1 1 calc R . . . .
H15B H -0.4625 0.3245 -0.4917 0.069 Uiso 1 1 calc R . . . .
C16 C 0.0124(5) 0.0478(5) -0.6191(4) 0.0563(14) Uani 1 1 d . . . . .
H16 H 0.0877 0.0244 -0.5756 0.068 Uiso 1 1 calc R . . . .
C17 C 0.0511(4) 0.0155(5) -0.3403(4) 0.0417(11) Uani 1 1 d . . . . .
C18 C 0.0598(4) 0.1581(5) -0.3406(4) 0.0453(12) Uani 1 1 d . . . . .
H18 H 0.0316 0.2084 -0.3991 0.054 Uiso 1 1 calc R . . . .
C19 C 0.1111(5) 0.2273(5) -0.2525(4) 0.0513(13) Uani 1 1 d . . . . .
H19 H 0.1170 0.3245 -0.2524 0.062 Uiso 1 1 calc R . . . .
C20 C 0.1535(5) 0.1544(6) -0.1650(4) 0.0570(14) Uani 1 1 d . . . . .
C21 C 0.1438(5) 0.0097(6) -0.1675(4) 0.0642(16) Uani 1 1 d . . . . .
H21 H 0.1723 -0.0413 -0.1093 0.077 Uiso 1 1 calc R . . . .
C22 C 0.0925(5) -0.0610(5) -0.2551(4) 0.0520(13) Uani 1 1 d . . . . .
H22 H 0.0864 -0.1582 -0.2559 0.062 Uiso 1 1 calc R . . . .
C23 C 0.2096(7) 0.2289(8) -0.0693(4) 0.092(2) Uani 1 1 d . . . . .
H23A H 0.2981 0.2524 -0.0708 0.137 Uiso 1 1 calc GR . . . .
H23B H 0.2052 0.1688 -0.0131 0.137 Uiso 1 1 calc GR . . . .
H23C H 0.1615 0.3130 -0.0631 0.137 Uiso 1 1 calc GR . . . .
O3 O -0.2619(4) 0.5513(5) -0.2567(4) 0.0912(15) Uani 1 1 d . . . . .
H3 H -0.1863 0.5607 -0.2632 0.137 Uiso 1 1 calc GR . . . .
C24 C -0.2997(7) 0.2724(6) -0.0279(4) 0.0716(18) Uani 1 1 d . . . . .
C25 C -0.1829(7) 0.2838(6) -0.0620(5) 0.0750(18) Uani 1 1 d . . . . .
H25 H -0.1135 0.2283 -0.0337 0.090 Uiso 1 1 calc R . . . .
C26 C -0.1684(6) 0.3767(6) -0.1376(4) 0.0706(18) Uani 1 1 d . . . . .
H26 H -0.0896 0.3827 -0.1599 0.085 Uiso 1 1 calc R . . . .
C27 C -0.2694(6) 0.4605(6) -0.1800(5) 0.0660(17) Uani 1 1 d . . . . .
C28 C -0.3986(7) 0.3571(7) -0.0707(5) 0.079(2) Uani 1 1 d . . . . .
H28 H -0.4769 0.3521 -0.0475 0.095 Uiso 1 1 calc R . . . .
C29 C -0.3869(6) 0.4495(6) -0.1468(5) 0.0762(19) Uani 1 1 d . . . . .
H29 H -0.4568 0.5039 -0.1756 0.091 Uiso 1 1 calc R . . . .
C30 C -0.3137(8) 0.1687(8) 0.0556(5) 0.107(3) Uani 1 1 d . . . . .
H30A H -0.3263 0.0761 0.0280 0.161 Uiso 1 1 calc GR . . . .
H30B H -0.3867 0.1944 0.0859 0.161 Uiso 1 1 calc GR . . . .
H30C H -0.2370 0.1704 0.1055 0.161 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 C16 1.242(6) . ?
O2 C1 1.384(5) . ?
O2 C17 1.407(5) . ?
N1 C1 1.330(5) . ?
N1 C5 1.485(5) . ?
N1 C9 1.464(5) . ?
N2 C7 1.469(5) . ?
N2 C12 1.473(6) . ?
N2 C13 1.474(6) . ?
C1 C2 1.373(6) . ?
C2 C3 1.503(7) . ?
C2 C16 1.403(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.527(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.527(6) . ?
C5 H5 0.9800 . ?
C5 C6 1.532(6) . ?
C6 H6 0.9800 . ?
C6 C7 1.535(6) . ?
C6 C15 1.525(6) . ?
C7 H7 0.9800 . ?
C7 C8 1.534(6) . ?
C8 H8 0.9800 . ?
C8 C9 1.513(6) . ?
C8 C10 1.530(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.516(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.506(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.510(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.510(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16 0.9300 . ?
C17 C18 1.364(6) . ?
C17 C22 1.371(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.389(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.380(7) . ?
C20 C21 1.385(7) . ?
C20 C23 1.507(8) . ?
C21 H21 0.9300 . ?
C21 C22 1.390(7) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O3 H3 0.8200 . ?
O3 C27 1.363(6) . ?
C24 C25 1.387(8) . ?
C24 C28 1.367(9) . ?
C24 C30 1.527(9) . ?
C25 H25 0.9300 . ?
C25 C26 1.380(8) . ?
C26 H26 0.9300 . ?
C26 C27 1.375(8) . ?
C27 C29 1.387(7) . ?
C28 H28 0.9300 . ?
C28 C29 1.377(8) . ?
C29 H29 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?

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
C1 O2 C17 114.9(3) . . ?
C1 N1 C5 121.8(4) . . ?
C1 N1 C9 124.3(4) . . ?
C9 N1 C5 113.8(3) . . ?
C7 N2 C12 110.7(4) . . ?
C7 N2 C13 110.7(3) . . ?
C12 N2 C13 107.8(4) . . ?
N1 C1 O2 115.8(4) . . ?
N1 C1 C2 124.5(4) . . ?
C2 C1 O2 119.6(4) . . ?
C1 C2 C3 115.5(4) . . ?
C1 C2 C16 121.3(5) . . ?
C16 C2 C3 123.2(4) . . ?
C2 C3 H3A 110.1 . . ?
C2 C3 H3B 110.1 . . ?
C2 C3 C4 107.9(4) . . ?
H3A C3 H3B 108.4 . . ?
C4 C3 H3A 110.1 . . ?
C4 C3 H3B 110.1 . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 C3 111.6(4) . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
N1 C5 C4 111.1(3) . . ?
N1 C5 H5 108.2 . . ?
N1 C5 C6 108.1(3) . . ?
C4 C5 H5 108.2 . . ?
C4 C5 C6 112.8(4) . . ?
C6 C5 H5 108.2 . . ?
C5 C6 H6 107.3 . . ?
C5 C6 C7 112.7(3) . . ?
C7 C6 H6 107.3 . . ?
C15 C6 C5 112.1(4) . . ?
C15 C6 H6 107.3 . . ?
C15 C6 C7 109.7(4) . . ?
N2 C7 C6 111.4(4) . . ?
N2 C7 H7 108.2 . . ?
N2 C7 C8 110.8(3) . . ?
C6 C7 H7 108.2 . . ?
C8 C7 C6 110.1(3) . . ?
C8 C7 H7 108.2 . . ?
C7 C8 H8 108.1 . . ?
C9 C8 C7 110.0(4) . . ?
C9 C8 H8 108.1 . . ?
C9 C8 C10 110.9(4) . . ?
C10 C8 C7 111.5(4) . . ?
C10 C8 H8 108.1 . . ?
N1 C9 C8 110.8(3) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C8 C10 H10A 109.3 . . ?
C8 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 C8 111.6(4) . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 C10 110.7(4) . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
N2 C12 C11 111.4(4) . . ?
N2 C12 H12A 109.4 . . ?
N2 C12 H12B 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
N2 C13 H13A 109.3 . . ?
N2 C13 H13B 109.3 . . ?
N2 C13 C14 111.7(4) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 C13 110.7(5) . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C6 C15 H15A 109.5 . . ?
C6 C15 H15B 109.5 . . ?
C14 C15 C6 110.8(4) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
O1 C16 C2 125.1(5) . . ?
O1 C16 H16 117.5 . . ?
C2 C16 H16 117.5 . . ?
C18 C17 O2 121.3(5) . . ?
C18 C17 C22 121.5(5) . . ?
C22 C17 O2 117.3(4) . . ?
C17 C18 H18 120.4 . . ?
C17 C18 C19 119.2(5) . . ?
C19 C18 H18 120.4 . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.2(5) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 C21 118.1(5) . . ?
C19 C20 C23 121.4(5) . . ?
C21 C20 C23 120.5(6) . . ?
C20 C21 H21 119.3 . . ?
C20 C21 C22 121.4(5) . . ?
C22 C21 H21 119.3 . . ?
C17 C22 C21 118.7(5) . . ?
C17 C22 H22 120.7 . . ?
C21 C22 H22 120.7 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C27 O3 H3 109.5 . . ?
C25 C24 C30 119.9(7) . . ?
C28 C24 C25 117.8(6) . . ?
C28 C24 C30 122.3(6) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 C24 120.8(7) . . ?
C26 C25 H25 119.6 . . ?
C25 C26 H26 119.7 . . ?
C27 C26 C25 120.6(6) . . ?
C27 C26 H26 119.7 . . ?
O3 C27 C26 123.2(5) . . ?
O3 C27 C29 117.6(6) . . ?
C26 C27 C29 119.2(6) . . ?
C24 C28 H28 118.7 . . ?
C24 C28 C29 122.5(6) . . ?
C29 C28 H28 118.7 . . ?
C27 C29 H29 120.4 . . ?
C28 C29 C27 119.2(6) . . ?
C28 C29 H29 120.4 . . ?
C24 C30 H30A 109.5 . . ?
C24 C30 H30B 109.5 . . ?
C24 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

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
O2 C1 C2 C3 172.4(4) . . . . ?
O2 C1 C2 C16 -9.6(7) . . . . ?
O2 C17 C18 C19 -178.7(4) . . . . ?
O2 C17 C22 C21 178.6(4) . . . . ?
N1 C1 C2 C3 -5.1(7) . . . . ?
N1 C1 C2 C16 172.9(4) . . . . ?
N1 C5 C6 C7 -54.1(5) . . . . ?
N1 C5 C6 C15 -178.5(4) . . . . ?
N2 C7 C8 C9 69.7(4) . . . . ?
N2 C7 C8 C10 -53.8(5) . . . . ?
N2 C13 C14 C15 -56.6(6) . . . . ?
C1 O2 C17 C18 -43.5(6) . . . . ?
C1 O2 C17 C22 138.1(4) . . . . ?
C1 N1 C5 C4 -0.6(6) . . . . ?
C1 N1 C5 C6 -124.9(4) . . . . ?
C1 N1 C9 C8 122.1(4) . . . . ?
C1 C2 C3 C4 43.0(6) . . . . ?
C1 C2 C16 O1 178.4(5) . . . . ?
C2 C3 C4 C5 -59.7(6) . . . . ?
C3 C2 C16 O1 -3.7(8) . . . . ?
C3 C4 C5 N1 39.2(5) . . . . ?
C3 C4 C5 C6 160.7(4) . . . . ?
C4 C5 C6 C7 -177.4(4) . . . . ?
C4 C5 C6 C15 58.2(5) . . . . ?
C5 N1 C1 O2 164.3(3) . . . . ?
C5 N1 C1 C2 -18.1(7) . . . . ?
C5 N1 C9 C8 -60.6(5) . . . . ?
C5 C6 C7 N2 -69.3(4) . . . . ?
C5 C6 C7 C8 54.0(5) . . . . ?
C5 C6 C15 C14 71.8(5) . . . . ?
C6 C7 C8 C9 -53.9(5) . . . . ?
C6 C7 C8 C10 -177.4(4) . . . . ?
C7 N2 C12 C11 -61.5(5) . . . . ?
C7 N2 C13 C14 58.5(6) . . . . ?
C7 C6 C15 C14 -54.2(5) . . . . ?
C7 C8 C9 N1 57.0(5) . . . . ?
C7 C8 C10 C11 50.2(5) . . . . ?
C8 C10 C11 C12 -51.7(5) . . . . ?
C9 N1 C1 O2 -18.6(6) . . . . ?
C9 N1 C1 C2 159.0(4) . . . . ?
C9 N1 C5 C4 -178.0(4) . . . . ?
C9 N1 C5 C6 57.7(4) . . . . ?
C9 C8 C10 C11 -72.7(5) . . . . ?
C10 C8 C9 N1 -179.2(4) . . . . ?
C10 C11 C12 N2 57.3(6) . . . . ?
C12 N2 C7 C6 -178.0(4) . . . . ?
C12 N2 C7 C8 59.1(5) . . . . ?
C12 N2 C13 C14 179.7(4) . . . . ?
C13 N2 C7 C6 -58.5(5) . . . . ?
C13 N2 C7 C8 178.6(4) . . . . ?
C13 N2 C12 C11 177.3(4) . . . . ?
C13 C14 C15 C6 54.6(6) . . . . ?
C15 C6 C7 N2 56.4(5) . . . . ?
C15 C6 C7 C8 179.7(4) . . . . ?
C16 C2 C3 C4 -135.0(5) . . . . ?
C17 O2 C1 N1 -63.6(5) . . . . ?
C17 O2 C1 C2 118.7(4) . . . . ?
C17 C18 C19 C20 0.1(8) . . . . ?
C18 C17 C22 C21 0.2(7) . . . . ?
C18 C19 C20 C21 0.2(8) . . . . ?
C18 C19 C20 C23 179.8(5) . . . . ?
C19 C20 C21 C22 -0.3(9) . . . . ?
C20 C21 C22 C17 0.1(8) . . . . ?
C22 C17 C18 C19 -0.3(7) . . . . ?
C23 C20 C21 C22 -179.9(5) . . . . ?
O3 C27 C29 C28 178.9(5) . . . . ?
C24 C25 C26 C27 0.4(9) . . . . ?
C24 C28 C29 C27 -1.7(9) . . . . ?
C25 C24 C28 C29 1.4(9) . . . . ?
C25 C26 C27 O3 -178.1(5) . . . . ?
C25 C26 C27 C29 -0.7(9) . . . . ?
C26 C27 C29 C28 1.3(8) . . . . ?
C28 C24 C25 C26 -0.8(9) . . . . ?
C30 C24 C25 C26 179.9(5) . . . . ?
C30 C24 C28 C29 -179.2(5) . . . . ?

_olex2_date_sample_data_collection 2015-11-12
_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_hjl_39
_database_code_depnum_ccdc_archive 'CCDC 1524882'
_audit_update_record             
;
2016-12-29 deposited with the CCDC.
2017-02-27 downloaded from the CCDC.
;
_audit_creation_date             2015-11-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H27 Cl N2 O2'
_chemical_formula_sum            'C22 H27 Cl N2 O2'
_chemical_formula_weight         386.90
_chemical_absolute_configuration unk
_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 0.0033 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'
Cl Cl 0.1484 0.1585 '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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.1435(5)
_cell_length_b                   17.5376(12)
_cell_length_c                   18.5410(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1997.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1026
_cell_measurement_temperature    294.05(10)
_cell_measurement_theta_max      19.0350
_cell_measurement_theta_min      3.9730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67324
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.1173
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6083
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.494
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -49.00   47.00   1.2000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4291  -77.0000   30.0000 80

#__ type_ start__ end____ width___ exp.time_
  2 omega   -3.00   64.20   1.2000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4291   77.0000  -30.0000 56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0001774000
_diffrn_orient_matrix_UB_12      0.0282582000
_diffrn_orient_matrix_UB_13      -0.0273363000
_diffrn_orient_matrix_UB_21      0.0192746000
_diffrn_orient_matrix_UB_22      0.0285102000
_diffrn_orient_matrix_UB_23      0.0263705000
_diffrn_orient_matrix_UB_31      0.1139072000
_diffrn_orient_matrix_UB_32      -0.0048877000
_diffrn_orient_matrix_UB_33      -0.0044154000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.658
_reflns_Friedel_fraction_full    0.906
_reflns_Friedel_fraction_max     0.906
_reflns_number_gt                1728
_reflns_number_total             3778
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 441 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.05(13)
_refine_ls_extinction_coef       0.0088(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3778
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1570
_refine_ls_R_factor_gt           0.0677
_refine_ls_restrained_S_all      1.052
_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)+(0.0341P)²+0.0465P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1654
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C9(H9), C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B),
 C8(H8A,H8B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C18(H18), C19(H19), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Cl1 Cl -0.0059(4) 0.70766(12) 0.17616(11) 0.0956(9) Uani 1 1 d . . . . .
O1 O -0.9015(10) 1.0590(4) 0.0946(3) 0.100(2) Uani 1 1 d . . . . .
O2 O -0.4982(8) 0.9182(3) -0.0072(2) 0.0617(13) Uani 1 1 d . . . . .
N1 N -0.2702(10) 1.0140(3) -0.0473(3) 0.0578(16) Uani 1 1 d . . . . .
N2 N 0.0506(10) 1.0831(4) -0.1957(3) 0.0665(17) Uani 1 1 d . . . . .
C1 C -0.1603(14) 0.9630(4) -0.0968(4) 0.069(2) Uani 1 1 d . . . . .
H1A H -0.2011 0.9108 -0.0863 0.083 Uiso 1 1 calc R . . . .
H1B H -0.0040 0.9677 -0.0907 0.083 Uiso 1 1 calc R . . . .
C2 C -0.2222(13) 0.9827(4) -0.1745(4) 0.067(2) Uani 1 1 d . . . . .
H2 H -0.3784 0.9731 -0.1800 0.081 Uiso 1 1 calc R . . . .
C3 C -0.1024(15) 0.9318(5) -0.2285(4) 0.081(3) Uani 1 1 d . . . . .
H3A H -0.1155 0.8790 -0.2133 0.097 Uiso 1 1 calc R . . . .
H3B H -0.1712 0.9365 -0.2753 0.097 Uiso 1 1 calc R . . . .
C4 C 0.1359(15) 0.9518(5) -0.2353(5) 0.091(3) Uani 1 1 d . . . . .
H4A H 0.2011 0.9227 -0.2743 0.109 Uiso 1 1 calc R . . . .
H4B H 0.2116 0.9393 -0.1910 0.109 Uiso 1 1 calc R . . . .
C5 C 0.1564(13) 1.0366(5) -0.2507(4) 0.082(3) Uani 1 1 d . . . . .
H5A H 0.3093 1.0501 -0.2532 0.098 Uiso 1 1 calc R . . . .
H5B H 0.0915 1.0476 -0.2973 0.098 Uiso 1 1 calc R . . . .
C6 C 0.0897(14) 1.1631(5) -0.2148(4) 0.083(3) Uani 1 1 d . . . . .
H6A H 0.0287 1.1732 -0.2621 0.099 Uiso 1 1 calc R . . . .
H6B H 0.2453 1.1722 -0.2173 0.099 Uiso 1 1 calc R . . . .
C7 C -0.0104(17) 1.2175(5) -0.1604(5) 0.094(3) Uani 1 1 d . . . . .
H7A H 0.0111 1.2696 -0.1763 0.113 Uiso 1 1 calc R . . . .
H7B H 0.0613 1.2114 -0.1141 0.113 Uiso 1 1 calc R . . . .
C8 C -0.2539(15) 1.2017(4) -0.1520(4) 0.083(3) Uani 1 1 d . . . . .
H8A H -0.3289 1.2143 -0.1964 0.100 Uiso 1 1 calc R . . . .
H8B H -0.3129 1.2335 -0.1138 0.100 Uiso 1 1 calc R . . . .
C9 C -0.2909(13) 1.1177(4) -0.1337(4) 0.064(2) Uani 1 1 d . . . . .
H9 H -0.4479 1.1083 -0.1364 0.076 Uiso 1 1 calc R . . . .
C10 C -0.1822(12) 1.0670(4) -0.1906(4) 0.065(2) Uani 1 1 d . . . . .
H10 H -0.2483 1.0787 -0.2375 0.078 Uiso 1 1 calc R . . . .
C11 C -0.2167(13) 1.0945(4) -0.0588(3) 0.0580(19) Uani 1 1 d . . . . .
H11 H -0.0578 1.0992 -0.0575 0.070 Uiso 1 1 calc R . . . .
C12 C -0.3075(14) 1.1424(4) 0.0030(4) 0.073(2) Uani 1 1 d . . . . .
H12A H -0.2304 1.1300 0.0471 0.087 Uiso 1 1 calc R . . . .
H12B H -0.2834 1.1960 -0.0072 0.087 Uiso 1 1 calc R . . . .
C13 C -0.5501(14) 1.1284(4) 0.0138(4) 0.077(2) Uani 1 1 d . . . . .
H13A H -0.5997 1.1547 0.0569 0.092 Uiso 1 1 calc R . . . .
H13B H -0.6307 1.1482 -0.0271 0.092 Uiso 1 1 calc R . . . .
C14 C -0.5893(13) 1.0461(4) 0.0211(4) 0.062(2) Uani 1 1 d . . . . .
C15 C -0.4519(13) 0.9955(4) -0.0105(4) 0.0564(19) Uani 1 1 d . . . . .
C16 C -0.7659(14) 1.0189(5) 0.0627(4) 0.079(2) Uani 1 1 d . . . . .
H16 H -0.7818 0.9663 0.0664 0.095 Uiso 1 1 calc R . . . .
C17 C -0.3839(13) 0.8729(4) 0.0410(3) 0.0558(19) Uani 1 1 d . . . . .
C18 C -0.4552(13) 0.7987(4) 0.0479(3) 0.065(2) Uani 1 1 d . . . . .
H18 H -0.5791 0.7828 0.0234 0.079 Uiso 1 1 calc R . . . .
C19 C -0.3433(14) 0.7480(4) 0.0911(4) 0.070(2) Uani 1 1 d . . . . .
H19 H -0.3925 0.6981 0.0966 0.084 Uiso 1 1 calc R . . . .
C20 C -0.1578(13) 0.7722(4) 0.1260(4) 0.062(2) Uani 1 1 d . . . . .
C21 C -0.0901(13) 0.8465(4) 0.1217(4) 0.065(2) Uani 1 1 d . . . . .
H21 H 0.0314 0.8629 0.1473 0.078 Uiso 1 1 calc R . . . .
C22 C -0.2057(12) 0.8968(4) 0.0788(4) 0.064(2) Uani 1 1 d . . . . .
H22 H -0.1615 0.9474 0.0756 0.076 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
Cl1 C20 1.738(7) . ?
O1 C16 1.242(9) . ?
O2 C15 1.386(7) . ?
O2 C17 1.387(8) . ?
N1 C1 1.447(8) . ?
N1 C11 1.466(8) . ?
N1 C15 1.348(9) . ?
N2 C5 1.459(9) . ?
N2 C6 1.467(8) . ?
N2 C10 1.461(9) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.529(9) . ?
C2 H2 0.9800 . ?
C2 C3 1.530(10) . ?
C2 C10 1.529(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.511(10) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.520(10) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.518(11) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.529(11) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.529(9) . ?
C9 H9 0.9800 . ?
C9 C10 1.532(10) . ?
C9 C11 1.517(8) . ?
C10 H10 0.9800 . ?
C11 H11 0.9800 . ?
C11 C12 1.527(9) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.524(10) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.469(10) . ?
C14 C15 1.358(9) . ?
C14 C16 1.415(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(8) . ?
C17 C22 1.365(9) . ?
C18 H18 0.9300 . ?
C18 C19 1.380(9) . ?
C19 H19 0.9300 . ?
C19 C20 1.377(10) . ?
C20 C21 1.370(9) . ?
C21 H21 0.9300 . ?
C21 C22 1.385(9) . ?
C22 H22 0.9300 . ?

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
C17 O2 C15 119.0(5) . . ?
C1 N1 C11 113.5(6) . . ?
C15 N1 C1 124.0(6) . . ?
C15 N1 C11 119.4(6) . . ?
C5 N2 C6 107.1(6) . . ?
C5 N2 C10 111.9(6) . . ?
C10 N2 C6 111.1(7) . . ?
N1 C1 H1A 109.7 . . ?
N1 C1 H1B 109.7 . . ?
N1 C1 C2 110.0(6) . . ?
H1A C1 H1B 108.2 . . ?
C2 C1 H1A 109.7 . . ?
C2 C1 H1B 109.7 . . ?
C1 C2 H2 107.6 . . ?
C1 C2 C3 111.4(7) . . ?
C3 C2 H2 107.6 . . ?
C10 C2 C1 111.3(6) . . ?
C10 C2 H2 107.6 . . ?
C10 C2 C3 111.0(6) . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 C2 112.7(7) . . ?
C4 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C3 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
C3 C4 C5 108.9(7) . . ?
H4A C4 H4B 108.3 . . ?
C5 C4 H4A 109.9 . . ?
C5 C4 H4B 109.9 . . ?
N2 C5 C4 112.3(6) . . ?
N2 C5 H5A 109.1 . . ?
N2 C5 H5B 109.1 . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
N2 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
N2 C6 C7 111.9(7) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 C8 110.6(8) . . ?
H7A C7 H7B 108.1 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C7 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
C7 C8 C9 110.0(7) . . ?
H8A C8 H8B 108.2 . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C8 C9 H9 107.3 . . ?
C8 C9 C10 110.0(6) . . ?
C10 C9 H9 107.3 . . ?
C11 C9 C8 114.6(6) . . ?
C11 C9 H9 107.3 . . ?
C11 C9 C10 110.2(6) . . ?
N2 C10 C2 110.9(7) . . ?
N2 C10 C9 111.0(6) . . ?
N2 C10 H10 108.0 . . ?
C2 C10 C9 110.8(6) . . ?
C2 C10 H10 108.0 . . ?
C9 C10 H10 108.0 . . ?
N1 C11 C9 108.9(6) . . ?
N1 C11 H11 107.4 . . ?
N1 C11 C12 109.8(6) . . ?
C9 C11 H11 107.4 . . ?
C9 C11 C12 115.5(6) . . ?
C12 C11 H11 107.4 . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 C11 111.5(7) . . ?
C13 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C12 C13 H13A 109.8 . . ?
C12 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?
C14 C13 C12 109.3(7) . . ?
C14 C13 H13A 109.8 . . ?
C14 C13 H13B 109.8 . . ?
C15 C14 C13 120.1(7) . . ?
C15 C14 C16 119.4(8) . . ?
C16 C14 C13 120.5(8) . . ?
N1 C15 O2 115.3(7) . . ?
N1 C15 C14 125.1(7) . . ?
C14 C15 O2 119.6(7) . . ?
O1 C16 C14 125.7(9) . . ?
O1 C16 H16 117.2 . . ?
C14 C16 H16 117.2 . . ?
C18 C17 O2 116.1(7) . . ?
C22 C17 O2 124.1(7) . . ?
C22 C17 C18 119.8(7) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.3(7) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.5 . . ?
C20 C19 C18 119.0(7) . . ?
C20 C19 H19 120.5 . . ?
C19 C20 Cl1 119.7(6) . . ?
C21 C20 Cl1 119.1(6) . . ?
C21 C20 C19 121.2(7) . . ?
C20 C21 H21 120.6 . . ?
C20 C21 C22 118.9(7) . . ?
C22 C21 H21 120.6 . . ?
C17 C22 C21 120.7(7) . . ?
C17 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?

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
Cl1 C20 C21 C22 176.8(5) . . . . ?
O2 C17 C18 C19 175.8(6) . . . . ?
O2 C17 C22 C21 -175.0(6) . . . . ?
N1 C1 C2 C3 177.9(6) . . . . ?
N1 C1 C2 C10 53.4(9) . . . . ?
N1 C11 C12 C13 -53.7(8) . . . . ?
N2 C6 C7 C8 -55.8(9) . . . . ?
C1 N1 C11 C9 62.3(8) . . . . ?
C1 N1 C11 C12 -170.3(6) . . . . ?
C1 N1 C15 O2 16.6(10) . . . . ?
C1 N1 C15 C14 -162.0(7) . . . . ?
C1 C2 C3 C4 -73.1(9) . . . . ?
C1 C2 C10 N2 72.0(8) . . . . ?
C1 C2 C10 C9 -51.8(9) . . . . ?
C2 C3 C4 C5 -52.4(10) . . . . ?
C3 C2 C10 N2 -52.7(8) . . . . ?
C3 C2 C10 C9 -176.5(6) . . . . ?
C3 C4 C5 N2 56.5(9) . . . . ?
C5 N2 C6 C7 -179.1(7) . . . . ?
C5 N2 C10 C2 57.5(8) . . . . ?
C5 N2 C10 C9 -178.8(6) . . . . ?
C6 N2 C5 C4 177.6(7) . . . . ?
C6 N2 C10 C2 177.2(6) . . . . ?
C6 N2 C10 C9 -59.2(8) . . . . ?
C6 C7 C8 C9 53.9(8) . . . . ?
C7 C8 C9 C10 -54.8(9) . . . . ?
C7 C8 C9 C11 69.9(9) . . . . ?
C8 C9 C10 N2 57.7(8) . . . . ?
C8 C9 C10 C2 -178.5(6) . . . . ?
C8 C9 C11 N1 177.5(6) . . . . ?
C8 C9 C11 C12 53.4(9) . . . . ?
C9 C11 C12 C13 69.9(8) . . . . ?
C10 N2 C5 C4 -60.5(9) . . . . ?
C10 N2 C6 C7 58.4(9) . . . . ?
C10 C2 C3 C4 51.6(9) . . . . ?
C10 C9 C11 N1 -57.9(8) . . . . ?
C10 C9 C11 C12 178.0(6) . . . . ?
C11 N1 C1 C2 -59.7(8) . . . . ?
C11 N1 C15 O2 175.1(5) . . . . ?
C11 N1 C15 C14 -3.5(11) . . . . ?
C11 C9 C10 N2 -69.5(8) . . . . ?
C11 C9 C10 C2 54.2(8) . . . . ?
C11 C12 C13 C14 52.6(9) . . . . ?
C12 C13 C14 C15 -27.4(10) . . . . ?
C12 C13 C14 C16 150.6(7) . . . . ?
C13 C14 C15 O2 -175.8(6) . . . . ?
C13 C14 C15 N1 2.7(11) . . . . ?
C13 C14 C16 O1 1.3(13) . . . . ?
C15 O2 C17 C18 172.4(6) . . . . ?
C15 O2 C17 C22 -9.9(10) . . . . ?
C15 N1 C1 C2 99.9(8) . . . . ?
C15 N1 C11 C9 -98.4(7) . . . . ?
C15 N1 C11 C12 29.0(9) . . . . ?
C15 C14 C16 O1 179.4(7) . . . . ?
C16 C14 C15 O2 6.1(10) . . . . ?
C16 C14 C15 N1 -175.4(7) . . . . ?
C17 O2 C15 N1 78.2(8) . . . . ?
C17 O2 C15 C14 -103.1(8) . . . . ?
C17 C18 C19 C20 -1.2(11) . . . . ?
C18 C17 C22 C21 2.6(11) . . . . ?
C18 C19 C20 Cl1 -176.1(5) . . . . ?
C18 C19 C20 C21 3.8(11) . . . . ?
C19 C20 C21 C22 -3.1(11) . . . . ?
C20 C21 C22 C17 -0.1(11) . . . . ?
C22 C17 C18 C19 -2.0(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
