# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1038447'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2014-07-30T12:21:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        4aba
_chemical_name_common            lm1HF1027B
_chemical_formula_moiety         'C22 H23 N O3'
_chemical_formula_sum            'C22 H23 N O3'
_chemical_formula_weight         349.41

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.0325(7)
_cell_length_b                   20.594(2)
_cell_length_c                   14.3515(15)
_cell_angle_alpha                90
_cell_angle_beta                 97.425(5)
_cell_angle_gamma                90
_cell_volume                     1767.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9517
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      31.93
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.14
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  1.007
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.988

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_ub_11      0.081077
_diffrn_orient_matrix_ub_12      0.041848
_diffrn_orient_matrix_ub_13      -0.005948
_diffrn_orient_matrix_ub_21      -0.146144
_diffrn_orient_matrix_ub_22      0.022988
_diffrn_orient_matrix_ub_23      -0.015448
_diffrn_orient_matrix_ub_31      -0.003769
_diffrn_orient_matrix_ub_32      0.008845
_diffrn_orient_matrix_ub_33      0.068291
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_number            45525
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.739
_diffrn_reflns_theta_max         33.24
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.989
_reflns_number_total             6728
_reflns_number_gt                4778
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SIR-2011 (Burla et al., 2012)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0514P)²+0.3944P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6728
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.12
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.059

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C2 C 0.51121(18) 0.36478(5) 0.08868(7) 0.01320(19) Uani 1 d . .
H2 H 0.6264 0.3844 0.053 0.016 Uiso 1 calc . .
C3 C 0.28018(17) 0.37377(5) 0.03422(7) 0.01265(19) Uani 1 d . .
C4 C 0.14154(18) 0.42500(5) 0.07396(7) 0.0149(2) Uani 1 d . .
H4A H 0.0769 0.4075 0.1288 0.018 Uiso 1 calc . .
H4B H 0.0174 0.4386 0.026 0.018 Uiso 1 calc . .
C5 C 0.29181(19) 0.48303(5) 0.10378(7) 0.0150(2) Uani 1 d . .
H5A H 0.2008 0.5189 0.1248 0.018 Uiso 1 calc . .
H5B H 0.3631 0.4986 0.0496 0.018 Uiso 1 calc . .
C6 C 0.47350(18) 0.46328(5) 0.18436(7) 0.01328(19) Uani 1 d . .
C11 C 0.56911(17) 0.29457(5) 0.11134(7) 0.01240(19) Uani 1 d . .
C12 C 0.43057(19) 0.25860(5) 0.16285(7) 0.0159(2) Uani 1 d . .
H12 H 0.2963 0.2773 0.1784 0.019 Uiso 1 calc . .
C13 C 0.4875(2) 0.19583(5) 0.19135(8) 0.0192(2) Uani 1 d . .
H13 H 0.3935 0.172 0.2272 0.023 Uiso 1 calc . .
C14 C 0.6825(2) 0.16768(5) 0.16753(8) 0.0207(2) Uani 1 d . .
H14 H 0.7207 0.1245 0.1864 0.025 Uiso 1 calc . .
C15 C 0.8204(2) 0.20295(5) 0.11630(8) 0.0192(2) Uani 1 d . .
H15 H 0.9535 0.1838 0.1 0.023 Uiso 1 calc . .
C16 C 0.76466(19) 0.26639(5) 0.08846(7) 0.0156(2) Uani 1 d . .
H16 H 0.8605 0.2905 0.0538 0.019 Uiso 1 calc . .
C21 C 0.20247(18) 0.34150(5) -0.04363(7) 0.01385(19) Uani 1 d . .
H21 H 0.0564 0.3519 -0.0729 0.017 Uiso 1 calc . .
C23 C 0.52084(19) 0.30024(5) -0.11869(7) 0.0165(2) Uani 1 d . .
C25 C 0.4005(2) 0.19683(6) -0.15712(8) 0.0228(2) Uani 1 d . .
H25A H 0.4547 0.1541 -0.132 0.027 Uiso 1 calc . .
H25B H 0.3271 0.191 -0.2224 0.027 Uiso 1 calc . .
C26 C 0.2388(2) 0.22660(5) -0.09585(8) 0.0202(2) Uani 1 d . .
H26A H 0.0829 0.2252 -0.1273 0.024 Uiso 1 calc . .
H26B H 0.2474 0.2045 -0.0342 0.024 Uiso 1 calc . .
C30 C 0.68878(19) 0.50182(5) 0.18077(8) 0.0177(2) Uani 1 d . .
H30A H 0.7967 0.4909 0.2356 0.027 Uiso 1 calc . .
H30B H 0.6557 0.5484 0.1813 0.027 Uiso 1 calc . .
H30C H 0.7519 0.4909 0.1232 0.027 Uiso 1 calc . .
C31 C 0.38903(18) 0.47261(5) 0.27938(7) 0.0147(2) Uani 1 d . .
C32 C 0.3646(2) 0.42088(6) 0.33920(8) 0.0201(2) Uani 1 d . .
H32 H 0.3967 0.378 0.3204 0.024 Uiso 1 calc . .
C33 C 0.2932(2) 0.43132(7) 0.42675(8) 0.0255(3) Uani 1 d . .
H33 H 0.2772 0.3955 0.4671 0.031 Uiso 1 calc . .
C34 C 0.2459(2) 0.49336(7) 0.45497(8) 0.0252(3) Uani 1 d . .
H34 H 0.2002 0.5004 0.5151 0.03 Uiso 1 calc . .
C35 C 0.2655(2) 0.54514(6) 0.39512(8) 0.0228(2) Uani 1 d . .
H35 H 0.2296 0.5878 0.4137 0.027 Uiso 1 calc . .
C36 C 0.33730(19) 0.53513(5) 0.30796(7) 0.0182(2) Uani 1 d . .
H36 H 0.3513 0.571 0.2675 0.022 Uiso 1 calc . .
N22 N 0.32192(16) 0.29276(4) -0.08600(6) 0.01476(18) Uani 1 d . .
O1 O 0.52217(13) 0.39473(4) 0.17962(5) 0.01570(16) Uani 1 d . .
O24 O 0.58400(14) 0.24280(4) -0.15403(6) 0.02162(18) Uani 1 d . .
O27 O 0.63479(14) 0.34890(4) -0.11855(6) 0.02116(18) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C2 O1 1.4374(12) . ?
C2 C11 1.5128(14) . ?
C2 C3 1.5186(15) . ?
C2 H2 1 . ?
C3 C21 1.3319(14) . ?
C3 C4 1.5037(14) . ?
C4 C5 1.5272(15) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 C6 1.5416(14) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 O1 1.4453(12) . ?
C6 C31 1.5283(14) . ?
C6 C30 1.5286(15) . ?
C11 C16 1.3915(15) . ?
C11 C12 1.3977(15) . ?
C12 C13 1.3856(15) . ?
C12 H12 0.95 . ?
C13 C14 1.3930(17) . ?
C13 H13 0.95 . ?
C14 C15 1.3849(17) . ?
C14 H14 0.95 . ?
C15 C16 1.3946(15) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C21 N22 1.4178(13) . ?
C21 H21 0.95 . ?
C23 O27 1.2151(14) . ?
C23 N22 1.3524(14) . ?
C23 O24 1.3607(13) . ?
C25 O24 1.4530(15) . ?
C25 C26 1.5236(16) . ?
C25 H25A 0.99 . ?
C25 H25B 0.99 . ?
C26 N22 1.4523(14) . ?
C26 H26A 0.99 . ?
C26 H26B 0.99 . ?
C30 H30A 0.98 . ?
C30 H30B 0.98 . ?
C30 H30C 0.98 . ?
C31 C32 1.3880(15) . ?
C31 C36 1.3987(15) . ?
C32 C33 1.3966(16) . ?
C32 H32 0.95 . ?
C33 C34 1.3813(19) . ?
C33 H33 0.95 . ?
C34 C35 1.3838(18) . ?
C34 H34 0.95 . ?
C35 C36 1.3911(15) . ?
C35 H35 0.95 . ?
C36 H36 0.95 . ?

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
O1 C2 C11 103.45(8) . . ?
O1 C2 C3 110.27(8) . . ?
C11 C2 C3 113.47(8) . . ?
O1 C2 H2 109.8 . . ?
C11 C2 H2 109.8 . . ?
C3 C2 H2 109.8 . . ?
C21 C3 C4 121.03(10) . . ?
C21 C3 C2 124.82(9) . . ?
C4 C3 C2 114.13(8) . . ?
C3 C4 C5 108.43(9) . . ?
C3 C4 H4A 110 . . ?
C5 C4 H4A 110 . . ?
C3 C4 H4B 110 . . ?
C5 C4 H4B 110 . . ?
H4A C4 H4B 108.4 . . ?
C4 C5 C6 110.03(8) . . ?
C4 C5 H5A 109.7 . . ?
C6 C5 H5A 109.7 . . ?
C4 C5 H5B 109.7 . . ?
C6 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
O1 C6 C31 104.95(8) . . ?
O1 C6 C30 109.09(9) . . ?
C31 C6 C30 110.33(8) . . ?
O1 C6 C5 110.58(8) . . ?
C31 C6 C5 110.46(9) . . ?
C30 C6 C5 111.26(9) . . ?
C16 C11 C12 119.13(10) . . ?
C16 C11 C2 121.81(9) . . ?
C12 C11 C2 118.89(9) . . ?
C13 C12 C11 120.55(10) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.05(10) . . ?
C12 C13 H13 120 . . ?
C14 C13 H13 120 . . ?
C15 C14 C13 119.75(10) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.29(11) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 120.23(10) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C3 C21 N22 124.73(10) . . ?
C3 C21 H21 117.6 . . ?
N22 C21 H21 117.6 . . ?
O27 C23 N22 128.35(10) . . ?
O27 C23 O24 122.13(10) . . ?
N22 C23 O24 109.51(10) . . ?
O24 C25 C26 105.20(9) . . ?
O24 C25 H25A 110.7 . . ?
C26 C25 H25A 110.7 . . ?
O24 C25 H25B 110.7 . . ?
C26 C25 H25B 110.7 . . ?
H25A C25 H25B 108.8 . . ?
N22 C26 C25 101.25(9) . . ?
N22 C26 H26A 111.5 . . ?
C25 C26 H26A 111.5 . . ?
N22 C26 H26B 111.5 . . ?
C25 C26 H26B 111.5 . . ?
H26A C26 H26B 109.3 . . ?
C6 C30 H30A 109.5 . . ?
C6 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C6 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C32 C31 C36 118.66(10) . . ?
C32 C31 C6 121.98(10) . . ?
C36 C31 C6 119.35(9) . . ?
C31 C32 C33 120.53(11) . . ?
C31 C32 H32 119.7 . . ?
C33 C32 H32 119.7 . . ?
C34 C33 C32 120.38(11) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C33 C34 C35 119.55(11) . . ?
C33 C34 H34 120.2 . . ?
C35 C34 H34 120.2 . . ?
C34 C35 C36 120.37(11) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C35 C36 C31 120.49(10) . . ?
C35 C36 H36 119.8 . . ?
C31 C36 H36 119.8 . . ?
C23 N22 C21 126.23(9) . . ?
C23 N22 C26 112.56(9) . . ?
C21 N22 C26 121.19(9) . . ?
C2 O1 C6 118.43(7) . . ?
C23 O24 C25 109.19(9) . . ?

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 C3 C21 -166.17(9) . . . . ?
C11 C2 C3 C21 -50.66(14) . . . . ?
O1 C2 C3 C4 15.60(12) . . . . ?
C11 C2 C3 C4 131.11(9) . . . . ?
C21 C3 C4 C5 -136.97(10) . . . . ?
C2 C3 C4 C5 41.34(11) . . . . ?
C3 C4 C5 C6 -64.40(10) . . . . ?
C4 C5 C6 O1 27.40(11) . . . . ?
C4 C5 C6 C31 -88.33(10) . . . . ?
C4 C5 C6 C30 148.78(9) . . . . ?
O1 C2 C11 C16 -113.51(10) . . . . ?
C3 C2 C11 C16 127.00(10) . . . . ?
O1 C2 C11 C12 61.63(11) . . . . ?
C3 C2 C11 C12 -57.86(12) . . . . ?
C16 C11 C12 C13 0.40(15) . . . . ?
C2 C11 C12 C13 -174.87(9) . . . . ?
C11 C12 C13 C14 -0.96(16) . . . . ?
C12 C13 C14 C15 0.79(16) . . . . ?
C13 C14 C15 C16 -0.05(17) . . . . ?
C12 C11 C16 C15 0.34(15) . . . . ?
C2 C11 C16 C15 175.46(9) . . . . ?
C14 C15 C16 C11 -0.51(16) . . . . ?
C4 C3 C21 N22 179.75(9) . . . . ?
C2 C3 C21 N22 1.64(17) . . . . ?
O24 C25 C26 N22 14.24(11) . . . . ?
O1 C6 C31 C32 -2.31(14) . . . . ?
C30 C6 C31 C32 -119.69(11) . . . . ?
C5 C6 C31 C32 116.89(11) . . . . ?
O1 C6 C31 C36 176.81(9) . . . . ?
C30 C6 C31 C36 59.43(13) . . . . ?
C5 C6 C31 C36 -63.99(12) . . . . ?
C36 C31 C32 C33 -1.01(17) . . . . ?
C6 C31 C32 C33 178.11(10) . . . . ?
C31 C32 C33 C34 0.02(19) . . . . ?
C32 C33 C34 C35 1.24(19) . . . . ?
C33 C34 C35 C36 -1.49(19) . . . . ?
C34 C35 C36 C31 0.49(18) . . . . ?
C32 C31 C36 C35 0.76(17) . . . . ?
C6 C31 C36 C35 -178.38(11) . . . . ?
O27 C23 N22 C21 -0.08(18) . . . . ?
O24 C23 N22 C21 179.68(9) . . . . ?
O27 C23 N22 C26 -178.30(11) . . . . ?
O24 C23 N22 C26 1.46(12) . . . . ?
C3 C21 N22 C23 -59.69(15) . . . . ?
C3 C21 N22 C26 118.39(12) . . . . ?
C25 C26 N22 C23 -10.05(12) . . . . ?
C25 C26 N22 C21 171.62(9) . . . . ?
C11 C2 O1 C6 -179.56(8) . . . . ?
C3 C2 O1 C6 -57.90(11) . . . . ?
C31 C6 O1 C2 153.42(9) . . . . ?
C30 C6 O1 C2 -88.36(10) . . . . ?
C5 C6 O1 C2 34.30(12) . . . . ?
O27 C23 O24 C25 -171.62(10) . . . . ?
N22 C23 O24 C25 8.60(11) . . . . ?
C26 C25 O24 C23 -14.57(12) . . . . ?



# END of CIF
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1038448'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2013-11-26T13:23:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        4aha
_chemical_name_common            lm1iv2-O11-3
_chemical_formula_moiety         'C25 H27 N O3'
_chemical_formula_sum            'C25 H27 N O3'
_chemical_formula_weight         389.48

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.6026(4)
_cell_length_b                   12.0053(4)
_cell_length_c                   16.5199(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.806(2)
_cell_angle_gamma                90
_cell_volume                     2023.27(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9773
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      30.53
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_T_max  0.988
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.992

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_ub_11      -0.075064
_diffrn_orient_matrix_ub_12      -0.053026
_diffrn_orient_matrix_ub_13      -0.018648
_diffrn_orient_matrix_ub_21      -0.031948
_diffrn_orient_matrix_ub_22      0.042191
_diffrn_orient_matrix_ub_23      -0.053906
_diffrn_orient_matrix_ub_31      0.054344
_diffrn_orient_matrix_ub_32      -0.04844
_diffrn_orient_matrix_ub_33      -0.026538
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_number            38710
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.057
_diffrn_reflns_theta_max         30.568
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_number_total             6193
_reflns_number_gt                4628
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SIR-2011 (Burla et al., 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0476P)²+0.8598P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6193
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.072
_refine_ls_R_factor_gt           0.048
_refine_ls_wR_factor_ref         0.1173
_refine_ls_wR_factor_gt          0.1066
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.049

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.50004(8) 0.23148(7) 0.20488(5) 0.01403(17) Uani 1 d . .
C2 C 0.58088(11) 0.27575(10) 0.15434(8) 0.0147(2) Uani 1 d . .
H2 H 0.5786 0.2229 0.1072 0.018 Uiso 1 calc . .
C3 C 0.53466(11) 0.38935(10) 0.11778(7) 0.0156(2) Uani 1 d . .
C4 C 0.38817(12) 0.40685(11) 0.09110(8) 0.0193(2) Uani 1 d . .
H4A H 0.3507 0.3689 0.0366 0.023 Uiso 1 calc . .
H4B H 0.3695 0.4875 0.0827 0.023 Uiso 1 calc . .
C5 C 0.32210(12) 0.36226(10) 0.15584(8) 0.0170(2) Uani 1 d . .
H5 H 0.225 0.3668 0.1314 0.02 Uiso 1 calc . .
C6 C 0.35935(12) 0.43155(10) 0.23605(9) 0.0206(3) Uani 1 d . .
H6A H 0.3273 0.5087 0.2227 0.025 Uiso 1 calc . .
H6B H 0.4561 0.4345 0.2572 0.025 Uiso 1 calc . .
C7 C 0.30341(13) 0.38566(11) 0.30519(8) 0.0222(3) Uani 1 d . .
H7A H 0.333 0.4323 0.3563 0.027 Uiso 1 calc . .
H7B H 0.2065 0.3881 0.2864 0.027 Uiso 1 calc . .
C8 C 0.34906(13) 0.26586(11) 0.32556(8) 0.0210(3) Uani 1 d . .
H8A H 0.3092 0.2352 0.3685 0.025 Uiso 1 calc . .
H8B H 0.4455 0.2642 0.3488 0.025 Uiso 1 calc . .
C9 C 0.30929(12) 0.19473(10) 0.24608(8) 0.0173(2) Uani 1 d . .
H9A H 0.2124 0.1904 0.227 0.021 Uiso 1 calc . .
H9B H 0.3431 0.1182 0.2599 0.021 Uiso 1 calc . .
C10 C 0.35983(11) 0.23935(10) 0.17365(7) 0.0139(2) Uani 1 d . .
C11 C 0.71654(11) 0.27373(10) 0.21515(8) 0.0164(2) Uani 1 d . .
C12 C 0.74683(12) 0.33988(12) 0.28691(8) 0.0222(3) Uani 1 d . .
H12 H 0.6834 0.3906 0.2961 0.027 Uiso 1 calc . .
C13 C 0.86858(13) 0.33268(13) 0.34527(9) 0.0284(3) Uani 1 d . .
H13 H 0.8877 0.3783 0.3941 0.034 Uiso 1 calc . .
C14 C 0.96230(13) 0.25950(13) 0.33275(10) 0.0314(3) Uani 1 d . .
H14 H 1.046 0.2551 0.3724 0.038 Uiso 1 calc . .
C15 C 0.93268(14) 0.19304(13) 0.26211(11) 0.0329(3) Uani 1 d . .
H15 H 0.9964 0.1426 0.253 0.039 Uiso 1 calc . .
C16 C 0.81025(13) 0.19926(11) 0.20411(10) 0.0253(3) Uani 1 d . .
H16 H 0.7906 0.1518 0.1563 0.03 Uiso 1 calc . .
C21 C 0.61149(12) 0.46879(10) 0.10083(7) 0.0161(2) Uani 1 d . .
H21 H 0.5727 0.5395 0.0843 0.019 Uiso 1 calc . .
N22 N 0.74559(10) 0.45662(8) 0.10541(6) 0.0157(2) Uani 1 d . .
C23 C 0.84016(12) 0.54596(11) 0.13482(9) 0.0216(3) Uani 1 d . .
H23A H 0.8503 0.5638 0.1948 0.026 Uiso 1 calc . .
H23B H 0.8157 0.6143 0.1006 0.026 Uiso 1 calc . .
C24 C 0.96312(13) 0.49240(12) 0.12174(9) 0.0276(3) Uani 1 d . .
H24A H 1.0157 0.5477 0.1006 0.033 Uiso 1 calc . .
H24B H 1.0179 0.4606 0.1751 0.033 Uiso 1 calc . .
O25 O 0.91614(9) 0.40552(8) 0.06014(6) 0.0259(2) Uani 1 d . .
C26 C 0.78876(12) 0.38277(11) 0.05607(8) 0.0183(2) Uani 1 d . .
O27 O 0.72863(9) 0.30824(8) 0.01371(6) 0.0244(2) Uani 1 d . .
C31 C 0.30624(12) 0.16196(10) 0.09881(7) 0.0168(2) Uani 1 d . .
C32 C 0.37770(13) 0.06911(11) 0.08666(8) 0.0204(3) Uani 1 d . .
H32 H 0.4656 0.0602 0.1198 0.025 Uiso 1 calc . .
C33 C 0.32177(14) -0.01092(13) 0.02643(9) 0.0288(3) Uani 1 d . .
H33 H 0.3718 -0.0736 0.0186 0.035 Uiso 1 calc . .
C34 C 0.19367(15) 0.00065(14) -0.02190(9) 0.0327(4) Uani 1 d . .
H34 H 0.1548 -0.0547 -0.062 0.039 Uiso 1 calc . .
C35 C 0.12280(14) 0.09335(14) -0.01139(9) 0.0308(3) Uani 1 d . .
H35 H 0.0353 0.1022 -0.0453 0.037 Uiso 1 calc . .
C36 C 0.17778(13) 0.17363(12) 0.04803(8) 0.0243(3) Uani 1 d . .
H36 H 0.1278 0.2371 0.0543 0.029 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C10 1.4378(13) . ?
O1 C2 1.4506(14) . ?
C2 C11 1.5137(16) . ?
C2 C3 1.5178(16) . ?
C2 H2 1 . ?
C3 C21 1.3326(16) . ?
C3 C4 1.5092(16) . ?
C4 C5 1.5262(17) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 C6 1.5228(18) . ?
C5 C10 1.5361(16) . ?
C5 H5 1 . ?
C6 C7 1.5261(18) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 C8 1.5255(19) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 C9 1.5263(18) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 C10 1.5347(16) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 C31 1.5271(16) . ?
C11 C16 1.3851(17) . ?
C11 C12 1.3900(18) . ?
C12 C13 1.3875(18) . ?
C12 H12 0.95 . ?
C13 C14 1.383(2) . ?
C13 H13 0.95 . ?
C14 C15 1.378(2) . ?
C14 H14 0.95 . ?
C15 C16 1.390(2) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C21 N22 1.4106(15) . ?
C21 H21 0.95 . ?
N22 C26 1.3650(16) . ?
N22 C23 1.4583(15) . ?
C23 C24 1.5210(19) . ?
C23 H23A 0.99 . ?
C23 H23B 0.99 . ?
C24 O25 1.4475(16) . ?
C24 H24A 0.99 . ?
C24 H24B 0.99 . ?
O25 C26 1.3615(15) . ?
C26 O27 1.2057(15) . ?
C31 C32 1.3927(18) . ?
C31 C36 1.3986(18) . ?
C32 C33 1.3940(18) . ?
C32 H32 0.95 . ?
C33 C34 1.382(2) . ?
C33 H33 0.95 . ?
C34 C35 1.380(2) . ?
C34 H34 0.95 . ?
C35 C36 1.386(2) . ?
C35 H35 0.95 . ?
C36 H36 0.95 . ?

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
C10 O1 C2 118.99(8) . . ?
O1 C2 C11 102.46(9) . . ?
O1 C2 C3 112.39(9) . . ?
C11 C2 C3 115.08(10) . . ?
O1 C2 H2 108.9 . . ?
C11 C2 H2 108.9 . . ?
C3 C2 H2 108.9 . . ?
C21 C3 C4 118.58(11) . . ?
C21 C3 C2 125.24(11) . . ?
C4 C3 C2 115.87(10) . . ?
C3 C4 C5 112.26(10) . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 C4 111.00(10) . . ?
C6 C5 C10 111.45(10) . . ?
C4 C5 C10 109.02(10) . . ?
C6 C5 H5 108.4 . . ?
C4 C5 H5 108.4 . . ?
C10 C5 H5 108.4 . . ?
C5 C6 C7 113.11(10) . . ?
C5 C6 H6A 109 . . ?
C7 C6 H6A 109 . . ?
C5 C6 H6B 109 . . ?
C7 C6 H6B 109 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C6 109.92(10) . . ?
C8 C7 H7A 109.7 . . ?
C6 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
C6 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C7 C8 C9 109.94(11) . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C8 C9 C10 113.71(10) . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
O1 C10 C31 111.77(9) . . ?
O1 C10 C9 104.11(9) . . ?
C31 C10 C9 106.67(9) . . ?
O1 C10 C5 108.77(9) . . ?
C31 C10 C5 114.16(10) . . ?
C9 C10 C5 110.90(10) . . ?
C16 C11 C12 118.28(12) . . ?
C16 C11 C2 120.60(12) . . ?
C12 C11 C2 120.92(11) . . ?
C13 C12 C11 120.80(13) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C12 120.40(14) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 119.15(13) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 120.51(13) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C15 120.85(14) . . ?
C11 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C3 C21 N22 125.42(11) . . ?
C3 C21 H21 117.3 . . ?
N22 C21 H21 117.3 . . ?
C26 N22 C21 122.15(10) . . ?
C26 N22 C23 111.39(10) . . ?
C21 N22 C23 122.22(10) . . ?
N22 C23 C24 100.36(10) . . ?
N22 C23 H23A 111.7 . . ?
C24 C23 H23A 111.7 . . ?
N22 C23 H23B 111.7 . . ?
C24 C23 H23B 111.7 . . ?
H23A C23 H23B 109.5 . . ?
O25 C24 C23 105.09(10) . . ?
O25 C24 H24A 110.7 . . ?
C23 C24 H24A 110.7 . . ?
O25 C24 H24B 110.7 . . ?
C23 C24 H24B 110.7 . . ?
H24A C24 H24B 108.8 . . ?
C26 O25 C24 109.03(10) . . ?
O27 C26 O25 122.56(12) . . ?
O27 C26 N22 128.19(12) . . ?
O25 C26 N22 109.25(10) . . ?
C32 C31 C36 118.22(12) . . ?
C32 C31 C10 120.44(11) . . ?
C36 C31 C10 120.76(11) . . ?
C31 C32 C33 120.81(13) . . ?
C31 C32 H32 119.6 . . ?
C33 C32 H32 119.6 . . ?
C34 C33 C32 120.20(14) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C35 C34 C33 119.43(13) . . ?
C35 C34 H34 120.3 . . ?
C33 C34 H34 120.3 . . ?
C34 C35 C36 120.77(13) . . ?
C34 C35 H35 119.6 . . ?
C36 C35 H35 119.6 . . ?
C35 C36 C31 120.55(14) . . ?
C35 C36 H36 119.7 . . ?
C31 C36 H36 119.7 . . ?

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
C10 O1 C2 C11 168.61(9) . . . . ?
C10 O1 C2 C3 44.52(13) . . . . ?
O1 C2 C3 C21 150.05(11) . . . . ?
C11 C2 C3 C21 33.28(17) . . . . ?
O1 C2 C3 C4 -36.41(14) . . . . ?
C11 C2 C3 C4 -153.19(10) . . . . ?
C21 C3 C4 C5 -142.03(12) . . . . ?
C2 C3 C4 C5 43.98(15) . . . . ?
C3 C4 C5 C6 68.53(13) . . . . ?
C3 C4 C5 C10 -54.61(13) . . . . ?
C4 C5 C6 C7 -176.02(10) . . . . ?
C10 C5 C6 C7 -54.29(13) . . . . ?
C5 C6 C7 C8 57.45(14) . . . . ?
C6 C7 C8 C9 -56.68(14) . . . . ?
C7 C8 C9 C10 56.02(13) . . . . ?
C2 O1 C10 C31 70.21(12) . . . . ?
C2 O1 C10 C9 -175.02(9) . . . . ?
C2 O1 C10 C5 -56.73(12) . . . . ?
C8 C9 C10 O1 64.21(12) . . . . ?
C8 C9 C10 C31 -177.46(10) . . . . ?
C8 C9 C10 C5 -52.60(13) . . . . ?
C6 C5 C10 O1 -63.61(12) . . . . ?
C4 C5 C10 O1 59.27(12) . . . . ?
C6 C5 C10 C31 170.83(10) . . . . ?
C4 C5 C10 C31 -66.30(13) . . . . ?
C6 C5 C10 C9 50.31(13) . . . . ?
C4 C5 C10 C9 173.18(10) . . . . ?
O1 C2 C11 C16 109.96(12) . . . . ?
C3 C2 C11 C16 -127.75(13) . . . . ?
O1 C2 C11 C12 -64.77(13) . . . . ?
C3 C2 C11 C12 57.51(15) . . . . ?
C16 C11 C12 C13 1.01(19) . . . . ?
C2 C11 C12 C13 175.86(12) . . . . ?
C11 C12 C13 C14 0.2(2) . . . . ?
C12 C13 C14 C15 -0.7(2) . . . . ?
C13 C14 C15 C16 0.0(2) . . . . ?
C12 C11 C16 C15 -1.8(2) . . . . ?
C2 C11 C16 C15 -176.63(12) . . . . ?
C14 C15 C16 C11 1.3(2) . . . . ?
C4 C3 C21 N22 -166.16(11) . . . . ?
C2 C3 C21 N22 7.2(2) . . . . ?
C3 C21 N22 C26 61.99(17) . . . . ?
C3 C21 N22 C23 -143.13(13) . . . . ?
C26 N22 C23 C24 -19.22(14) . . . . ?
C21 N22 C23 C24 -176.52(11) . . . . ?
N22 C23 C24 O25 21.33(14) . . . . ?
C23 C24 O25 C26 -17.57(15) . . . . ?
C24 O25 C26 O27 -174.84(13) . . . . ?
C24 O25 C26 N22 5.67(14) . . . . ?
C21 N22 C26 O27 -12.7(2) . . . . ?
C23 N22 C26 O27 -169.97(13) . . . . ?
C21 N22 C26 O25 166.80(10) . . . . ?
C23 N22 C26 O25 9.48(14) . . . . ?
O1 C10 C31 C32 22.71(15) . . . . ?
C9 C10 C31 C32 -90.47(13) . . . . ?
C5 C10 C31 C32 146.68(11) . . . . ?
O1 C10 C31 C36 -166.18(11) . . . . ?
C9 C10 C31 C36 80.63(13) . . . . ?
C5 C10 C31 C36 -42.21(15) . . . . ?
C36 C31 C32 C33 -1.07(19) . . . . ?
C10 C31 C32 C33 170.26(12) . . . . ?
C31 C32 C33 C34 -0.4(2) . . . . ?
C32 C33 C34 C35 1.5(2) . . . . ?
C33 C34 C35 C36 -1.2(2) . . . . ?
C34 C35 C36 C31 -0.3(2) . . . . ?
C32 C31 C36 C35 1.39(19) . . . . ?
C10 C31 C36 C35 -169.91(12) . . . . ?



# END of CIF
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1038449'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2014-09-23T18:51:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        4aia
_chemical_formula_moiety         'C24 H25 N O3'
_chemical_formula_sum            'C24 H25 N O3'
_chemical_formula_weight         375.45

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.6584(5)
_cell_length_b                   6.7792(2)
_cell_length_c                   14.6200(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.6090(10)
_cell_angle_gamma                90
_cell_volume                     1885.39(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9914
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      33.05
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.54
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_T_max  0.963
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.955

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_ub_11      0.047173
_diffrn_orient_matrix_ub_12      0.019478
_diffrn_orient_matrix_ub_13      0.044799
_diffrn_orient_matrix_ub_21      0.008065
_diffrn_orient_matrix_ub_22      0.118199
_diffrn_orient_matrix_ub_23      -0.036818
_diffrn_orient_matrix_ub_31      -0.02175
_diffrn_orient_matrix_ub_32      0.086076
_diffrn_orient_matrix_ub_33      0.04042
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_number            85307
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.141
_diffrn_reflns_theta_max         33.238
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_number_total             7249
_reflns_number_gt                5746
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXT (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0657P)²+0.3286P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7249
_refine_ls_number_parameters     355
_refine_ls_number_restraints     6
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1189
_refine_ls_wR_factor_gt          0.1095
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.24
_refine_diff_density_rms         0.052

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.19876(3) 0.26805(9) 0.27109(4) 0.01522(12) Uani 1 d . .
C2 C 0.27156(4) 0.28675(12) 0.31733(5) 0.01412(14) Uani 1 d . .
C3 C 0.31638(4) 0.25226(12) 0.24803(6) 0.01464(14) Uani 1 d . .
C4 C 0.27749(4) 0.13573(12) 0.16414(6) 0.01661(15) Uani 1 d . .
C5 C 0.21384(4) 0.25421(12) 0.10839(5) 0.01455(14) Uani 1 d . .
C6 C 0.17562(4) 0.35501(11) 0.17809(5) 0.01389(14) Uani 1 d . .
C11 C 0.28778(4) 0.12733(12) 0.39287(5) 0.01426(14) Uani 1 d . .
C12 C 0.24330(4) -0.03345(12) 0.38997(6) 0.01694(15) Uani 1 d . .
C13 C 0.26095(5) -0.18212(13) 0.45768(6) 0.01956(16) Uani 1 d . .
C14 C 0.32293(5) -0.17235(14) 0.52858(6) 0.02002(16) Uani 1 d . .
C15 C 0.36728(4) -0.01153(14) 0.53193(6) 0.01979(16) Uani 1 d . .
C16 C 0.34981(4) 0.13757(14) 0.46487(6) 0.01821(16) Uani 1 d . .
C21 C 0.38224(4) 0.31163(13) 0.25552(6) 0.01666(15) Uani 1 d . .
N22 N 0.42247(4) 0.44136(12) 0.32351(5) 0.01801(14) Uani 1 d . .
C23 C 0.49403(4) 0.44041(15) 0.33981(6) 0.02119(17) Uani 1 d . .
O24 O 0.52166(3) 0.59991(12) 0.39227(5) 0.02574(15) Uani 1 d . .
C25 C 0.46532(5) 0.72781(16) 0.40369(7) 0.02487(19) Uani 1 d . .
C26A C 0.3991(2) 0.6091(7) 0.3682(4) 0.0210(7) Uani 0.547(16) d A 1
H26A H 0.3793 0.5672 0.421 0.025 Uiso 0.547(16) calc A 1
H26B H 0.3632 0.6856 0.3222 0.025 Uiso 0.547(16) calc A 1
C26B C 0.3965(2) 0.6403(10) 0.3401(5) 0.0236(9) Uani 0.453(16) d A 2
H26C H 0.3585 0.6338 0.3734 0.028 Uiso 0.453(16) calc A 2
H26D H 0.38 0.7153 0.2805 0.028 Uiso 0.453(16) calc A 2
O27 O 0.53015(4) 0.31783(13) 0.31490(5) 0.03149(17) Uani 1 d . .
C30 C 0.19094(5) 0.57762(12) 0.18324(6) 0.01793(15) Uani 1 d . .
C31 C 0.09625(4) 0.32552(12) 0.15275(6) 0.01508(14) Uani 1 d . .
C32 C 0.05957(5) 0.36263(14) 0.22131(6) 0.02039(17) Uani 1 d . .
C33 C -0.01304(5) 0.34466(15) 0.20045(7) 0.02428(18) Uani 1 d . .
C34 C -0.04982(5) 0.28948(14) 0.11022(7) 0.02435(19) Uani 1 d . .
C35 C -0.01404(5) 0.25468(13) 0.04144(7) 0.02208(17) Uani 1 d . .
C36 C 0.05896(4) 0.27296(12) 0.06133(6) 0.01710(15) Uani 1 d . .
C37 C 0.09783(5) 0.22976(14) -0.01266(6) 0.01996(16) Uani 1 d . .
C38 C 0.16633(5) 0.12540(13) 0.03315(6) 0.01800(15) Uani 1 d . .
H2 H 0.2807(6) 0.4158(17) 0.3483(8) 0.013(2) Uiso 1 d . .
H5 H 0.2322(6) 0.3662(17) 0.0743(8) 0.016(3) Uiso 1 d . .
H4A H 0.3076(7) 0.1028(19) 0.1215(9) 0.025(3) Uiso 1 d . .
H4B H 0.2604(6) 0.010(2) 0.1856(8) 0.024(3) Uiso 1 d . .
H12 H 0.1985(6) -0.0411(19) 0.3405(8) 0.021(3) Uiso 1 d . .
H13 H 0.2280(7) -0.299(2) 0.4540(9) 0.031(3) Uiso 1 d . .
H14 H 0.3336(7) -0.277(2) 0.5757(9) 0.027(3) Uiso 1 d . .
H15 H 0.4117(7) -0.006(2) 0.5828(9) 0.029(3) Uiso 1 d . .
H16 H 0.3797(6) 0.2503(18) 0.4659(9) 0.022(3) Uiso 1 d . .
H21 H 0.4083(7) 0.2640(19) 0.2099(9) 0.025(3) Uiso 1 d . .
H25A H 0.4719(8) 0.750(2) 0.4717(10) 0.037(4) Uiso 1 d . .
H25B H 0.4689(7) 0.852(2) 0.3713(10) 0.038(4) Uiso 1 d . .
H32 H 0.0865(6) 0.4004(19) 0.2845(9) 0.024(3) Uiso 1 d . .
H33 H -0.0384(7) 0.370(2) 0.2512(10) 0.035(4) Uiso 1 d . .
H34 H -0.1012(8) 0.276(2) 0.0971(10) 0.035(4) Uiso 1 d . .
H35 H -0.0392(7) 0.216(2) -0.0248(10) 0.032(3) Uiso 1 d . .
H30A H 0.1713(7) 0.640(2) 0.2323(9) 0.029(3) Uiso 1 d . .
H30B H 0.1703(6) 0.637(2) 0.1210(9) 0.025(3) Uiso 1 d . .
H30C H 0.2428(7) 0.609(2) 0.1987(9) 0.026(3) Uiso 1 d . .
H37A H 0.0680(7) 0.147(2) -0.0635(10) 0.034(3) Uiso 1 d . .
H37B H 0.1074(6) 0.3558(19) -0.0440(8) 0.022(3) Uiso 1 d . .
H38A H 0.1934(6) 0.0920(19) -0.0129(9) 0.023(3) Uiso 1 d . .
H38B H 0.1560(7) 0.001(2) 0.0636(9) 0.029(3) Uiso 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.4259(9) . ?
O1 C6 1.4461(9) . ?
C2 C3 1.5192(11) . ?
C2 C11 1.5205(11) . ?
C2 H2 0.981(11) . ?
C3 C21 1.3337(11) . ?
C3 C4 1.4966(11) . ?
C4 C5 1.5365(12) . ?
C4 H4A 0.988(12) . ?
C4 H4B 0.993(13) . ?
C5 C38 1.5254(11) . ?
C5 C6 1.5673(11) . ?
C5 H5 1.023(11) . ?
C6 C31 1.5231(11) . ?
C6 C30 1.5370(11) . ?
C11 C12 1.3913(11) . ?
C11 C16 1.3973(11) . ?
C12 C13 1.3938(12) . ?
C12 H12 0.990(12) . ?
C13 C14 1.3881(13) . ?
C13 H13 1.018(14) . ?
C14 C15 1.3890(13) . ?
C14 H14 0.972(13) . ?
C15 C16 1.3896(12) . ?
C15 H15 0.995(13) . ?
C16 H16 0.962(12) . ?
C21 N22 1.4109(11) . ?
C21 H21 0.991(13) . ?
N22 C23 1.3661(11) . ?
N22 C26A 1.443(4) . ?
N22 C26B 1.484(6) . ?
C23 O27 1.2075(12) . ?
C23 O24 1.3574(12) . ?
O24 C25 1.4489(12) . ?
C25 C26A 1.507(4) . ?
C25 C26B 1.554(5) . ?
C25 H25A 0.982(14) . ?
C25 H25B 0.980(15) . ?
C26A H26A 0.99 . ?
C26A H26B 0.99 . ?
C26B H26C 0.99 . ?
C26B H26D 0.99 . ?
C30 H30A 0.991(13) . ?
C30 H30B 0.985(13) . ?
C30 H30C 1.010(12) . ?
C31 C32 1.3972(12) . ?
C31 C36 1.3988(11) . ?
C32 C33 1.3879(12) . ?
C32 H32 0.976(12) . ?
C33 C34 1.3863(14) . ?
C33 H33 1.009(14) . ?
C34 C35 1.3851(14) . ?
C34 H34 0.985(14) . ?
C35 C36 1.3960(12) . ?
C35 H35 1.005(14) . ?
C36 C37 1.5023(12) . ?
C37 C38 1.5189(12) . ?
C37 H37A 0.995(14) . ?
C37 H37B 1.009(13) . ?
C38 H38A 0.984(12) . ?
C38 H38B 1.000(14) . ?

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 C6 116.72(6) . . ?
O1 C2 C3 110.60(6) . . ?
O1 C2 C11 106.42(6) . . ?
C3 C2 C11 108.93(6) . . ?
O1 C2 H2 110.1(6) . . ?
C3 C2 H2 112.1(6) . . ?
C11 C2 H2 108.5(6) . . ?
C21 C3 C4 120.75(7) . . ?
C21 C3 C2 127.82(7) . . ?
C4 C3 C2 111.44(7) . . ?
C3 C4 C5 109.76(7) . . ?
C3 C4 H4A 111.9(7) . . ?
C5 C4 H4A 108.7(7) . . ?
C3 C4 H4B 109.6(7) . . ?
C5 C4 H4B 108.7(7) . . ?
H4A C4 H4B 108.1(10) . . ?
C38 C5 C4 110.61(7) . . ?
C38 C5 C6 114.31(7) . . ?
C4 C5 C6 110.05(6) . . ?
C38 C5 H5 107.5(6) . . ?
C4 C5 H5 107.8(6) . . ?
C6 C5 H5 106.2(6) . . ?
O1 C6 C31 103.60(6) . . ?
O1 C6 C30 110.05(6) . . ?
C31 C6 C30 108.47(6) . . ?
O1 C6 C5 110.18(6) . . ?
C31 C6 C5 114.48(6) . . ?
C30 C6 C5 109.86(6) . . ?
C12 C11 C16 118.96(8) . . ?
C12 C11 C2 121.31(7) . . ?
C16 C11 C2 119.68(7) . . ?
C11 C12 C13 120.19(8) . . ?
C11 C12 H12 120.0(7) . . ?
C13 C12 H12 119.8(7) . . ?
C14 C13 C12 120.68(8) . . ?
C14 C13 H13 120.2(7) . . ?
C12 C13 H13 119.1(7) . . ?
C13 C14 C15 119.25(8) . . ?
C13 C14 H14 119.1(8) . . ?
C15 C14 H14 121.6(8) . . ?
C14 C15 C16 120.32(8) . . ?
C14 C15 H15 118.8(8) . . ?
C16 C15 H15 120.9(8) . . ?
C15 C16 C11 120.58(8) . . ?
C15 C16 H16 121.7(7) . . ?
C11 C16 H16 117.7(7) . . ?
C3 C21 N22 127.30(7) . . ?
C3 C21 H21 120.1(8) . . ?
N22 C21 H21 112.6(7) . . ?
C23 N22 C21 119.30(7) . . ?
C23 N22 C26A 110.89(17) . . ?
C21 N22 C26A 128.61(18) . . ?
C23 N22 C26B 111.0(2) . . ?
C21 N22 C26B 121.8(2) . . ?
O27 C23 O24 122.46(8) . . ?
O27 C23 N22 127.50(9) . . ?
O24 C23 N22 110.02(8) . . ?
C23 O24 C25 109.47(7) . . ?
O24 C25 C26A 105.06(17) . . ?
O24 C25 C26B 106.2(2) . . ?
O24 C25 H25A 107.4(9) . . ?
C26A C25 H25A 108.2(9) . . ?
C26B C25 H25A 122.5(9) . . ?
O24 C25 H25B 108.1(8) . . ?
C26A C25 H25B 117.1(9) . . ?
C26B C25 H25B 101.4(9) . . ?
H25A C25 H25B 110.5(12) . . ?
N22 C26A C25 103.3(2) . . ?
N22 C26A H26A 111.1 . . ?
C25 C26A H26A 111.1 . . ?
N22 C26A H26B 111.1 . . ?
C25 C26A H26B 111.1 . . ?
H26A C26A H26B 109.1 . . ?
N22 C26B C25 99.2(3) . . ?
N22 C26B H26C 111.9 . . ?
C25 C26B H26C 111.9 . . ?
N22 C26B H26D 111.9 . . ?
C25 C26B H26D 111.9 . . ?
H26C C26B H26D 109.6 . . ?
C6 C30 H30A 110.3(8) . . ?
C6 C30 H30B 109.2(8) . . ?
H30A C30 H30B 110.4(11) . . ?
C6 C30 H30C 112.9(8) . . ?
H30A C30 H30C 107.8(10) . . ?
H30B C30 H30C 106.2(10) . . ?
C32 C31 C36 119.37(8) . . ?
C32 C31 C6 118.96(7) . . ?
C36 C31 C6 121.57(7) . . ?
C33 C32 C31 120.98(8) . . ?
C33 C32 H32 120.9(7) . . ?
C31 C32 H32 118.1(7) . . ?
C34 C33 C32 119.57(9) . . ?
C34 C33 H33 120.7(8) . . ?
C32 C33 H33 119.7(8) . . ?
C35 C34 C33 119.88(8) . . ?
C35 C34 H34 121.8(8) . . ?
C33 C34 H34 118.3(8) . . ?
C34 C35 C36 121.16(9) . . ?
C34 C35 H35 121.9(8) . . ?
C36 C35 H35 117.0(8) . . ?
C35 C36 C31 119.02(8) . . ?
C35 C36 C37 121.04(8) . . ?
C31 C36 C37 119.91(7) . . ?
C36 C37 C38 109.19(7) . . ?
C36 C37 H37A 109.7(8) . . ?
C38 C37 H37A 110.8(8) . . ?
C36 C37 H37B 110.4(7) . . ?
C38 C37 H37B 110.4(7) . . ?
H37A C37 H37B 106.3(10) . . ?
C37 C38 C5 111.40(7) . . ?
C37 C38 H38A 112.2(7) . . ?
C5 C38 H38A 106.6(7) . . ?
C37 C38 H38B 109.5(7) . . ?
C5 C38 H38B 108.6(7) . . ?
H38A C38 H38B 108.4(10) . . ?

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
C6 O1 C2 C3 -41.66(9) . . . . ?
C6 O1 C2 C11 -159.83(6) . . . . ?
O1 C2 C3 C21 158.40(8) . . . . ?
C11 C2 C3 C21 -84.98(10) . . . . ?
O1 C2 C3 C4 -21.95(9) . . . . ?
C11 C2 C3 C4 94.67(8) . . . . ?
C21 C3 C4 C5 -116.17(9) . . . . ?
C2 C3 C4 C5 64.15(8) . . . . ?
C3 C4 C5 C38 -169.99(7) . . . . ?
C3 C4 C5 C6 -42.74(9) . . . . ?
C2 O1 C6 C31 -175.33(6) . . . . ?
C2 O1 C6 C30 -59.53(9) . . . . ?
C2 O1 C6 C5 61.77(8) . . . . ?
C38 C5 C6 O1 110.02(7) . . . . ?
C4 C5 C6 O1 -15.14(9) . . . . ?
C38 C5 C6 C31 -6.25(10) . . . . ?
C4 C5 C6 C31 -131.41(7) . . . . ?
C38 C5 C6 C30 -128.56(7) . . . . ?
C4 C5 C6 C30 106.27(8) . . . . ?
O1 C2 C11 C12 18.11(10) . . . . ?
C3 C2 C11 C12 -101.15(8) . . . . ?
O1 C2 C11 C16 -164.35(7) . . . . ?
C3 C2 C11 C16 76.39(9) . . . . ?
C16 C11 C12 C13 -0.46(12) . . . . ?
C2 C11 C12 C13 177.10(7) . . . . ?
C11 C12 C13 C14 -0.13(13) . . . . ?
C12 C13 C14 C15 0.44(13) . . . . ?
C13 C14 C15 C16 -0.16(13) . . . . ?
C14 C15 C16 C11 -0.44(13) . . . . ?
C12 C11 C16 C15 0.74(12) . . . . ?
C2 C11 C16 C15 -176.85(7) . . . . ?
C4 C3 C21 N22 171.62(8) . . . . ?
C2 C3 C21 N22 -8.76(15) . . . . ?
C3 C21 N22 C23 159.99(9) . . . . ?
C3 C21 N22 C26A -33.8(3) . . . . ?
C3 C21 N22 C26B -53.9(4) . . . . ?
C21 N22 C23 O27 -13.90(14) . . . . ?
C26A N22 C23 O27 177.6(3) . . . . ?
C26B N22 C23 O27 -163.4(4) . . . . ?
C21 N22 C23 O24 167.68(7) . . . . ?
C26A N22 C23 O24 -0.9(3) . . . . ?
C26B N22 C23 O24 18.2(4) . . . . ?
O27 C23 O24 C25 174.99(9) . . . . ?
N22 C23 O24 C25 -6.49(10) . . . . ?
C23 O24 C25 C26A 10.8(3) . . . . ?
C23 O24 C25 C26B -6.8(3) . . . . ?
C23 N22 C26A C25 7.3(4) . . . . ?
C21 N22 C26A C25 -159.85(15) . . . . ?
O24 C25 C26A N22 -10.6(4) . . . . ?
C23 N22 C26B C25 -20.5(5) . . . . ?
C21 N22 C26B C25 -169.14(19) . . . . ?
O24 C25 C26B N22 15.8(5) . . . . ?
O1 C6 C31 C32 43.38(9) . . . . ?
C30 C6 C31 C32 -73.54(9) . . . . ?
C5 C6 C31 C32 163.39(7) . . . . ?
O1 C6 C31 C36 -140.20(8) . . . . ?
C30 C6 C31 C36 102.88(9) . . . . ?
C5 C6 C31 C36 -20.20(11) . . . . ?
C36 C31 C32 C33 1.16(13) . . . . ?
C6 C31 C32 C33 177.66(8) . . . . ?
C31 C32 C33 C34 -0.14(15) . . . . ?
C32 C33 C34 C35 -0.64(15) . . . . ?
C33 C34 C35 C36 0.39(14) . . . . ?
C34 C35 C36 C31 0.63(13) . . . . ?
C34 C35 C36 C37 178.32(8) . . . . ?
C32 C31 C36 C35 -1.39(12) . . . . ?
C6 C31 C36 C35 -177.79(8) . . . . ?
C32 C31 C36 C37 -179.10(8) . . . . ?
C6 C31 C36 C37 4.50(12) . . . . ?
C35 C36 C37 C38 -141.29(8) . . . . ?
C31 C36 C37 C38 36.38(11) . . . . ?
C36 C37 C38 C5 -61.43(9) . . . . ?
C4 C5 C38 C37 171.41(7) . . . . ?
C6 C5 C38 C37 46.54(9) . . . . ?



# END of CIF
_chemical_name_common            ' lm1HF1105B'
