# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_DG180F1
_database_code_depnum_ccdc_archive 'CCDC 2110269'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;Institut des Sciences Chimiques de Rennes
France
;
_audit_update_record             
;
2021-09-16 deposited with the CCDC.	2021-11-18 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 13 fevrier 2014                                                       #
#------------------------------------------------------------------------------#


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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C25 H30 N2 O3'
_chemical_formula_sum            'C25 H30 N2 O3'
_chemical_formula_weight         406.51
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration rm/ad/rmad/syn/unk/.

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#


_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
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                   7.4497(2)
_cell_length_b                   15.2211(5)
_cell_length_c                   19.6694(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2230.37(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4668
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      26.05
_cell_measurement_wavelength     0.71073


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.1283597
_diffrn_orient_matrix_UB_21      -0.0218035
_diffrn_orient_matrix_UB_31      -0.0326675
_diffrn_orient_matrix_UB_12      0.0054145
_diffrn_orient_matrix_UB_22      -0.0426087
_diffrn_orient_matrix_UB_32      0.0497135
_diffrn_orient_matrix_UB_13      -0.0142730
_diffrn_orient_matrix_UB_23      -0.0378067
_diffrn_orient_matrix_UB_33      -0.0308491


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

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.250
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             872
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_T_max  0.980

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

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

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.33
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_uneti/neti     0.0469
_diffrn_reflns_av_r_equivalents  0.0383
_diffrn_reflns_number            14181
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.692
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.979
_reflns_number_total             4968
_reflns_number_gt                4331
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_max     0.957
_reflns_Friedel_fraction_full    0.991

_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.
;

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

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2020)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0402P)²+0.2401P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4968
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1042
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_restrained_S_all      1.170
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
Flack x determined using 1567 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(6)

#------------------------------------------------------------------------------#
#               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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_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
C1 C 1.3409(3) 0.95043(17) 0.73276(13) 0.0277(5) Uani 1 1 d . . . . .
H1 H 1.407870 0.913980 0.762636 0.033 Uiso 1 1 calc R U . . .
C2 C 1.4032(3) 1.03427(17) 0.71675(14) 0.0305(6) Uani 1 1 d . . . . .
H2 H 1.512707 1.054532 0.735922 0.037 Uiso 1 1 calc R U . . .
C3 C 1.3079(4) 1.08822(18) 0.67341(13) 0.0332(6) Uani 1 1 d . . . . .
H3 H 1.351401 1.145210 0.662641 0.040 Uiso 1 1 calc R U . . .
C4 C 1.1487(4) 1.05846(19) 0.64589(14) 0.0351(6) Uani 1 1 d . . . . .
H4 H 1.081980 1.095103 0.616067 0.042 Uiso 1 1 calc R U . . .
C5 C 1.0862(3) 0.97537(18) 0.66168(13) 0.0318(6) Uani 1 1 d . . . . .
H5 H 0.976375 0.955607 0.642495 0.038 Uiso 1 1 calc R U . . .
C6 C 1.1811(3) 0.92015(16) 0.70512(12) 0.0236(5) Uani 1 1 d . . . . .
C7 C 1.1036(3) 0.82923(16) 0.71963(12) 0.0248(5) Uani 1 1 d . . . . .
H7 H 1.044405 0.809276 0.676703 0.030 Uiso 1 1 calc R U . . .
C8 C 1.2401(3) 0.75860(16) 0.73840(14) 0.0322(6) Uani 1 1 d . . . . .
H8A H 1.178108 0.702492 0.745197 0.048 Uiso 1 1 calc R U . . .
H8B H 1.301838 0.775386 0.780434 0.048 Uiso 1 1 calc R U . . .
H8C H 1.328000 0.752531 0.701638 0.048 Uiso 1 1 calc R U . . .
N9 N 0.9593(2) 0.83501(13) 0.77216(9) 0.0224(4) Uani 1 1 d . . . . .
C10 C 0.7888(3) 0.81050(15) 0.75859(12) 0.0207(5) Uani 1 1 d . . . . .
O11 O 0.6659(2) 0.81370(11) 0.80026(8) 0.0256(4) Uani 1 1 d . . . . .
C12 C 0.7434(3) 0.77803(15) 0.68807(12) 0.0206(5) Uani 1 1 d . . . . .
C13 C 0.7625(3) 0.68947(16) 0.67141(12) 0.0260(5) Uani 1 1 d . . . . .
H13 H 0.816687 0.650154 0.702807 0.031 Uiso 1 1 calc R U . . .
C14 C 0.7024(3) 0.65869(17) 0.60898(13) 0.0301(6) Uani 1 1 d . . . . .
H14 H 0.711408 0.598196 0.597600 0.036 Uiso 1 1 calc R U . . .
C15 C 0.6292(3) 0.71808(18) 0.56392(13) 0.0284(6) Uani 1 1 d . . . . .
C16 C 0.6103(3) 0.80616(18) 0.57869(12) 0.0283(6) Uani 1 1 d . . . . .
H16 H 0.560786 0.845572 0.546267 0.034 Uiso 1 1 calc R U . . .
C17 C 0.6651(3) 0.83569(16) 0.64183(12) 0.0251(5) Uani 1 1 d . . . . .
H17 H 0.649256 0.895677 0.653726 0.030 Uiso 1 1 calc R U . . .
N18 N 0.5739(3) 0.68621(18) 0.49641(12) 0.0427(6) Uani 1 1 d . . . . .
O19 O 0.5483(4) 0.60747(17) 0.48933(13) 0.0821(9) Uani 1 1 d . . . . .
O20 O 0.5533(3) 0.73971(16) 0.45107(10) 0.0568(6) Uani 1 1 d . . . . .
C21 C 1.0137(3) 0.86730(16) 0.84014(12) 0.0232(5) Uani 1 1 d . . . . .
H21 H 1.147691 0.868605 0.837321 0.028 Uiso 1 1 calc R U . . .
C22 C 0.9637(3) 0.96510(16) 0.85591(12) 0.0247(5) Uani 1 1 d . . . . .
H22 H 1.066033 1.000364 0.837564 0.030 Uiso 1 1 calc R U . . .
C23 C 0.9706(3) 0.97904(16) 0.93325(12) 0.0260(5) Uani 1 1 d . . . . .
H23 H 0.969583 1.042110 0.947495 0.031 Uiso 1 1 calc R U . . .
C24 C 1.1305(4) 0.92511(18) 0.96233(14) 0.0336(6) Uani 1 1 d . . . . .
H24A H 1.229568 0.915157 0.929680 0.040 Uiso 1 1 calc R U . . .
H24B H 1.175900 0.946369 1.006680 0.040 Uiso 1 1 calc R U . . .
C25 C 0.9950(3) 0.84841(18) 0.96740(13) 0.0307(6) Uani 1 1 d . . . . .
H25 H 1.012896 0.808492 1.007202 0.037 Uiso 1 1 calc R U . . .
C26 C 0.8451(3) 0.91833(17) 0.97650(13) 0.0272(5) Uani 1 1 d . . . . .
C27 C 0.8341(4) 0.9517(2) 1.04978(13) 0.0363(6) Uani 1 1 d . . . . .
H27A H 0.789157 0.904723 1.079273 0.054 Uiso 1 1 calc R U . . .
H27B H 0.752412 1.002095 1.051919 0.054 Uiso 1 1 calc R U . . .
H27C H 0.953814 0.969706 1.065068 0.054 Uiso 1 1 calc R U . . .
C28 C 0.6544(3) 0.89620(18) 0.95410(14) 0.0326(6) Uani 1 1 d . . . . .
H28A H 0.580863 0.949565 0.954858 0.049 Uiso 1 1 calc R U . . .
H28B H 0.603029 0.852597 0.985164 0.049 Uiso 1 1 calc R U . . .
H28C H 0.656849 0.872205 0.907873 0.049 Uiso 1 1 calc R U . . .
C29 C 0.9772(3) 0.80183(16) 0.89848(12) 0.0276(6) Uani 1 1 d . . . . .
H29A H 0.854763 0.777286 0.893780 0.033 Uiso 1 1 calc R U . . .
H29B H 1.063959 0.752665 0.896002 0.033 Uiso 1 1 calc R U . . .
C30 C 0.7968(4) 1.00363(17) 0.82209(13) 0.0308(6) Uani 1 1 d . . . . .
H30A H 0.784767 1.065619 0.834768 0.046 Uiso 1 1 calc R U . . .
H30B H 0.690341 0.971234 0.837197 0.046 Uiso 1 1 calc R U . . .
H30C H 0.808179 0.998778 0.772594 0.046 Uiso 1 1 calc R U . . .



#------------------------------------------------------------------------------#
#                              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
C1 C6 1.387(3) . ?
C1 C2 1.394(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.380(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.526(3) . ?
C7 N9 1.494(3) . ?
C7 C8 1.525(3) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
N9 C10 1.350(3) . ?
N9 C21 1.481(3) . ?
C10 O11 1.230(3) . ?
C10 C12 1.511(3) . ?
C12 C17 1.392(3) . ?
C12 C13 1.395(3) . ?
C13 C14 1.389(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(4) . ?
C15 N18 1.473(3) . ?
C16 C17 1.382(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
N18 O20 1.217(3) . ?
N18 O19 1.222(3) . ?
C21 C29 1.544(3) . ?
C21 C22 1.566(3) . ?
C21 H21 1.0000 . ?
C22 C30 1.527(3) . ?
C22 C23 1.537(3) . ?
C22 H22 1.0000 . ?
C23 C24 1.556(4) . ?
C23 C26 1.566(4) . ?
C23 H23 1.0000 . ?
C24 C25 1.546(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C29 1.535(3) . ?
C25 C26 1.553(4) . ?
C25 H25 1.0000 . ?
C26 C28 1.525(4) . ?
C26 C27 1.530(3) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.1(2) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 121.3(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 118.4(2) . . ?
C1 C6 C7 123.5(2) . . ?
C5 C6 C7 118.1(2) . . ?
N9 C7 C8 110.7(2) . . ?
N9 C7 C6 110.38(19) . . ?
C8 C7 C6 115.62(19) . . ?
N9 C7 H7 106.5 . . ?
C8 C7 H7 106.5 . . ?
C6 C7 H7 106.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 N9 C21 121.83(19) . . ?
C10 N9 C7 121.61(19) . . ?
C21 N9 C7 116.55(18) . . ?
O11 C10 N9 123.9(2) . . ?
O11 C10 C12 117.23(19) . . ?
N9 C10 C12 118.86(19) . . ?
C17 C12 C13 119.9(2) . . ?
C17 C12 C10 119.2(2) . . ?
C13 C12 C10 120.6(2) . . ?
C14 C13 C12 120.1(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 118.4(2) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C14 C15 C16 122.9(2) . . ?
C14 C15 N18 118.3(2) . . ?
C16 C15 N18 118.8(2) . . ?
C15 C16 C17 118.4(2) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
C16 C17 C12 120.4(2) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
O20 N18 O19 123.6(2) . . ?
O20 N18 C15 118.4(2) . . ?
O19 N18 C15 118.0(3) . . ?
N9 C21 C29 114.12(19) . . ?
N9 C21 C22 115.43(19) . . ?
C29 C21 C22 115.11(19) . . ?
N9 C21 H21 103.3 . . ?
C29 C21 H21 103.3 . . ?
C22 C21 H21 103.3 . . ?
C30 C22 C23 113.9(2) . . ?
C30 C22 C21 118.2(2) . . ?
C23 C22 C21 108.6(2) . . ?
C30 C22 H22 104.9 . . ?
C23 C22 H22 104.9 . . ?
C21 C22 H22 104.9 . . ?
C22 C23 C24 108.5(2) . . ?
C22 C23 C26 115.8(2) . . ?
C24 C23 C26 86.91(19) . . ?
C22 C23 H23 114.2 . . ?
C24 C23 H23 114.2 . . ?
C26 C23 H23 114.2 . . ?
C25 C24 C23 85.54(19) . . ?
C25 C24 H24A 114.4 . . ?
C23 C24 H24A 114.4 . . ?
C25 C24 H24B 114.4 . . ?
C23 C24 H24B 114.4 . . ?
H24A C24 H24B 111.5 . . ?
C29 C25 C24 110.4(2) . . ?
C29 C25 C26 110.9(2) . . ?
C24 C25 C26 87.69(19) . . ?
C29 C25 H25 115.0 . . ?
C24 C25 H25 115.0 . . ?
C26 C25 H25 115.0 . . ?
C28 C26 C27 107.2(2) . . ?
C28 C26 C25 119.0(2) . . ?
C27 C26 C25 112.0(2) . . ?
C28 C26 C23 122.0(2) . . ?
C27 C26 C23 110.3(2) . . ?
C25 C26 C23 84.96(19) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C29 C21 110.1(2) . . ?
C25 C29 H29A 109.6 . . ?
C21 C29 H29A 109.6 . . ?
C25 C29 H29B 109.6 . . ?
C21 C29 H29B 109.6 . . ?
H29A C29 H29B 108.2 . . ?
C22 C30 H30A 109.5 . . ?
C22 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C22 C30 H30C 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
C6 C1 C2 C3 0.0(4) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C2 C1 C6 C5 -0.2(4) . . . . ?
C2 C1 C6 C7 179.7(2) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C4 C5 C6 C7 -179.6(2) . . . . ?
C1 C6 C7 N9 99.9(3) . . . . ?
C5 C6 C7 N9 -80.2(3) . . . . ?
C1 C6 C7 C8 -26.7(3) . . . . ?
C5 C6 C7 C8 153.1(2) . . . . ?
C8 C7 N9 C10 -111.7(2) . . . . ?
C6 C7 N9 C10 119.0(2) . . . . ?
C8 C7 N9 C21 67.1(3) . . . . ?
C6 C7 N9 C21 -62.2(3) . . . . ?
C21 N9 C10 O11 0.9(4) . . . . ?
C7 N9 C10 O11 179.7(2) . . . . ?
C21 N9 C10 C12 -179.9(2) . . . . ?
C7 N9 C10 C12 -1.1(3) . . . . ?
O11 C10 C12 C17 80.7(3) . . . . ?
N9 C10 C12 C17 -98.5(3) . . . . ?
O11 C10 C12 C13 -92.8(3) . . . . ?
N9 C10 C12 C13 87.9(3) . . . . ?
C17 C12 C13 C14 -0.5(4) . . . . ?
C10 C12 C13 C14 173.1(2) . . . . ?
C12 C13 C14 C15 1.9(4) . . . . ?
C13 C14 C15 C16 -1.2(4) . . . . ?
C13 C14 C15 N18 177.0(2) . . . . ?
C14 C15 C16 C17 -0.8(4) . . . . ?
N18 C15 C16 C17 -179.1(2) . . . . ?
C15 C16 C17 C12 2.3(4) . . . . ?
C13 C12 C17 C16 -1.7(4) . . . . ?
C10 C12 C17 C16 -175.3(2) . . . . ?
C14 C15 N18 O20 -161.4(3) . . . . ?
C16 C15 N18 O20 16.9(4) . . . . ?
C14 C15 N18 O19 19.7(4) . . . . ?
C16 C15 N18 O19 -162.0(3) . . . . ?
C10 N9 C21 C29 57.9(3) . . . . ?
C7 N9 C21 C29 -121.0(2) . . . . ?
C10 N9 C21 C22 -78.8(3) . . . . ?
C7 N9 C21 C22 102.3(2) . . . . ?
N9 C21 C22 C30 29.7(3) . . . . ?
C29 C21 C22 C30 -106.6(2) . . . . ?
N9 C21 C22 C23 161.48(19) . . . . ?
C29 C21 C22 C23 25.2(3) . . . . ?
C30 C22 C23 C24 171.6(2) . . . . ?
C21 C22 C23 C24 37.6(3) . . . . ?
C30 C22 C23 C26 75.9(3) . . . . ?
C21 C22 C23 C26 -58.1(3) . . . . ?
C22 C23 C24 C25 -87.7(2) . . . . ?
C26 C23 C24 C25 28.55(17) . . . . ?
C23 C24 C25 C29 82.6(2) . . . . ?
C23 C24 C25 C26 -28.79(18) . . . . ?
C29 C25 C26 C28 41.7(3) . . . . ?
C24 C25 C26 C28 152.6(2) . . . . ?
C29 C25 C26 C27 167.8(2) . . . . ?
C24 C25 C26 C27 -81.3(2) . . . . ?
C29 C25 C26 C23 -82.3(2) . . . . ?
C24 C25 C26 C23 28.60(18) . . . . ?
C22 C23 C26 C28 -40.7(3) . . . . ?
C24 C23 C26 C28 -149.7(2) . . . . ?
C22 C23 C26 C27 -167.8(2) . . . . ?
C24 C23 C26 C27 83.2(2) . . . . ?
C22 C23 C26 C25 80.6(2) . . . . ?
C24 C23 C26 C25 -28.44(18) . . . . ?
C24 C25 C29 C21 -29.1(3) . . . . ?
C26 C25 C29 C21 66.4(3) . . . . ?
N9 C21 C29 C25 -166.5(2) . . . . ?
C22 C21 C29 C25 -29.7(3) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_DG266c
_database_code_depnum_ccdc_archive 'CCDC 2110271'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;Institut des Sciences Chimiques de Rennes
France
;
_audit_update_record             
;
2021-09-16 deposited with the CCDC.	2021-11-18 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 13/02/2014                                               #
#------------------------------------------------------------------------------#


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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H28 N, Cl'
_chemical_formula_sum            'C18 H28 Cl N'
_chemical_formula_weight         293.86
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

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

_cell_length_a                   11.0788(17)
_cell_length_b                   7.5785(11)
_cell_length_c                   11.6867(18)
_cell_angle_alpha                90
_cell_angle_beta                 118.618(5)
_cell_angle_gamma                90
_cell_volume                     861.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1763
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      22.76
_cell_measurement_wavelength     0.71073


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0274617
_diffrn_orient_matrix_UB_21      -0.0434003
_diffrn_orient_matrix_UB_31      0.0890788
_diffrn_orient_matrix_UB_12      0.1115226
_diffrn_orient_matrix_UB_22      -0.0434537
_diffrn_orient_matrix_UB_32      -0.0555520
_diffrn_orient_matrix_UB_13      0.0520858
_diffrn_orient_matrix_UB_23      0.0525669
_diffrn_orient_matrix_UB_33      0.0634453


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

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             320
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.592
_exptl_absorpt_correction_T_max  0.977

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

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

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.33
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_uneti/neti     0.0966
_diffrn_reflns_av_r_equivalents  0.0636
_diffrn_reflns_number            6699
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.342
_diffrn_reflns_theta_max         27.374
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.970
_reflns_number_total             3503
_reflns_number_gt                2299
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_max     0.823
_reflns_Friedel_fraction_full    0.862

_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.
;

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

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SIR97 (A. Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2020)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1133P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3503
_refine_ls_number_parameters     173
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1232
_refine_ls_R_factor_gt           0.0835
_refine_ls_wR_factor_ref         0.2176
_refine_ls_wR_factor_gt          0.1915
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.737
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details 
;
Flack x determined using 757 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(8)

#------------------------------------------------------------------------------#
#               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 0.0000 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'
Cl Cl 0.1484 0.1585 '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_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
C1 C 0.0270(8) 0.5865(9) -0.3277(7) 0.0541(18) Uani 1 1 d . . . . .
C2 C -0.1011(10) 0.5823(11) -0.4588(8) 0.072(2) Uani 1 1 d . . . . .
H2A H -0.112394 0.464245 -0.496816 0.109 Uiso 1 1 calc R U . . .
H2B H -0.092934 0.669187 -0.516739 0.109 Uiso 1 1 calc R U . . .
H2C H -0.181283 0.610619 -0.447750 0.109 Uiso 1 1 calc R U . . .
C3 C 0.1516(10) 0.5671(12) -0.3477(9) 0.072(2) Uani 1 1 d . . . . .
H3A H 0.233822 0.549760 -0.263220 0.108 Uiso 1 1 calc R U . . .
H3B H 0.162556 0.673902 -0.389140 0.108 Uiso 1 1 calc R U . . .
H3C H 0.139167 0.464971 -0.403788 0.108 Uiso 1 1 calc R U . . .
C4 C 0.0269(8) 0.7434(7) -0.2418(8) 0.0521(19) Uani 1 1 d . . . . .
H4 H -0.021246 0.851333 -0.292218 0.063 Uiso 1 1 calc R U . . .
C5 C 0.1661(8) 0.7792(7) -0.1240(8) 0.0487(17) Uani 1 1 d . . . . .
H5 H 0.234012 0.807471 -0.154701 0.058 Uiso 1 1 calc R U . . .
C6 C 0.1535(9) 0.9375(9) -0.0501(10) 0.073(3) Uani 1 1 d . . . . .
H6A H 0.126100 1.041591 -0.106786 0.110 Uiso 1 1 calc R U . . .
H6B H 0.242306 0.959769 0.027124 0.110 Uiso 1 1 calc R U . . .
H6C H 0.083957 0.913085 -0.023075 0.110 Uiso 1 1 calc R U . . .
C7 C 0.2159(8) 0.6115(7) -0.0355(7) 0.0448(16) Uani 1 1 d . . . . .
H7 H 0.186369 0.626360 0.032546 0.054 Uiso 1 1 calc R U . . .
C8 C 0.1500(8) 0.4374(8) -0.1089(7) 0.0512(19) Uani 1 1 d . . . . .
H8A H 0.212574 0.381009 -0.136383 0.061 Uiso 1 1 calc R U . . .
H8B H 0.138235 0.355361 -0.049046 0.061 Uiso 1 1 calc R U . . .
C9 C 0.0133(8) 0.4686(8) -0.2263(7) 0.0563(19) Uani 1 1 d . . . . .
H9 H -0.044285 0.360487 -0.263036 0.068 Uiso 1 1 calc R U . . .
C10 C -0.0616(8) 0.6261(9) -0.2014(8) 0.0532(18) Uani 1 1 d . . . . .
H10A H -0.161748 0.631566 -0.261691 0.064 Uiso 1 1 calc R U . . .
H10B H -0.040627 0.639922 -0.109488 0.064 Uiso 1 1 calc R U . . .
N11 N 0.3687(5) 0.5932(6) 0.0349(5) 0.0393(12) Uani 1 1 d . . . . .
H11A H 0.399964 0.616133 -0.022769 0.047 Uiso 1 1 calc R U . . .
H11B H 0.389123 0.478545 0.059901 0.047 Uiso 1 1 calc R U . . .
C12 C 0.4477(6) 0.7069(9) 0.1526(5) 0.0430(14) Uani 1 1 d . . . . .
H12 H 0.439549 0.832290 0.123239 0.052 Uiso 1 1 calc R U . . .
C13 C 0.6008(7) 0.6521(9) 0.2150(7) 0.0501(17) Uani 1 1 d . . . . .
H13A H 0.655782 0.729317 0.289291 0.075 Uiso 1 1 calc R U . . .
H13B H 0.632716 0.662932 0.150249 0.075 Uiso 1 1 calc R U . . .
H13C H 0.610836 0.529570 0.244913 0.075 Uiso 1 1 calc R U . . .
C14 C 0.3976(5) 0.6950(6) 0.2502(4) 0.0450(14) Uani 1 1 d G . . . .
C15 C 0.4072(6) 0.8463(5) 0.3213(5) 0.059(2) Uani 1 1 d G . . . .
H15 H 0.436002 0.954405 0.300994 0.071 Uiso 1 1 calc R U . . .
C16 C 0.3746(6) 0.8393(7) 0.4222(5) 0.070(2) Uani 1 1 d G . . . .
H16 H 0.381110 0.942707 0.470869 0.084 Uiso 1 1 calc R U . . .
C17 C 0.3324(6) 0.6811(9) 0.4520(5) 0.076(2) Uani 1 1 d G . . . .
H17 H 0.310106 0.676401 0.520953 0.091 Uiso 1 1 calc R U . . .
C18 C 0.3228(7) 0.5299(7) 0.3808(6) 0.073(3) Uani 1 1 d G . . . .
H18 H 0.293995 0.421792 0.401163 0.087 Uiso 1 1 calc R U . . .
C19 C 0.3554(6) 0.5369(5) 0.2799(5) 0.0532(19) Uani 1 1 d G . . . .
H19 H 0.348887 0.433486 0.231287 0.064 Uiso 1 1 calc R U . . .
Cl1 Cl 0.48210(16) 0.2013(2) 0.12480(15) 0.0483(5) Uani 1 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
C1 C3 1.514(12) . ?
C1 C2 1.510(12) . ?
C1 C9 1.549(10) . ?
C1 C4 1.556(9) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.521(11) . ?
C4 C10 1.555(10) . ?
C4 H4 1.0000 . ?
C5 C6 1.523(9) . ?
C5 C7 1.563(8) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 N11 1.493(9) . ?
C7 C8 1.553(9) . ?
C7 H7 1.0000 . ?
C8 C9 1.497(11) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.558(10) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
N11 C12 1.499(8) . ?
N11 H11A 0.9100 . ?
N11 H11B 0.9100 . ?
C12 C14 1.490(6) . ?
C12 C13 1.548(10) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.3900 . ?
C14 C19 1.3900 . ?
C15 C16 1.3900 . ?
C15 H15 0.9500 . ?
C16 C17 1.3900 . ?
C16 H16 0.9500 . ?
C17 C18 1.3900 . ?
C17 H17 0.9500 . ?
C18 C19 1.3900 . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C1 C2 109.0(7) . . ?
C3 C1 C9 119.6(7) . . ?
C2 C1 C9 112.0(7) . . ?
C3 C1 C4 117.2(6) . . ?
C2 C1 C4 112.3(6) . . ?
C9 C1 C4 85.2(5) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C10 109.9(6) . . ?
C5 C4 C1 114.0(6) . . ?
C10 C4 C1 87.4(5) . . ?
C5 C4 H4 114.2 . . ?
C10 C4 H4 114.2 . . ?
C1 C4 H4 114.2 . . ?
C6 C5 C4 109.0(6) . . ?
C6 C5 C7 111.4(6) . . ?
C4 C5 C7 109.7(5) . . ?
C6 C5 H5 108.9 . . ?
C4 C5 H5 108.9 . . ?
C7 C5 H5 108.9 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N11 C7 C8 109.5(5) . . ?
N11 C7 C5 112.8(5) . . ?
C8 C7 C5 113.7(5) . . ?
N11 C7 H7 106.8 . . ?
C8 C7 H7 106.8 . . ?
C5 C7 H7 106.8 . . ?
C9 C8 C7 111.9(5) . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C1 111.4(6) . . ?
C8 C9 C10 110.2(6) . . ?
C1 C9 C10 87.6(5) . . ?
C8 C9 H9 114.9 . . ?
C1 C9 H9 114.9 . . ?
C10 C9 H9 114.9 . . ?
C4 C10 C9 84.9(5) . . ?
C4 C10 H10A 114.5 . . ?
C9 C10 H10A 114.5 . . ?
C4 C10 H10B 114.5 . . ?
C9 C10 H10B 114.5 . . ?
H10A C10 H10B 111.6 . . ?
C7 N11 C12 117.5(5) . . ?
C7 N11 H11A 107.9 . . ?
C12 N11 H11A 107.9 . . ?
C7 N11 H11B 107.9 . . ?
C12 N11 H11B 107.9 . . ?
H11A N11 H11B 107.2 . . ?
C14 C12 N11 113.6(5) . . ?
C14 C12 C13 110.4(5) . . ?
N11 C12 C13 107.7(5) . . ?
C14 C12 H12 108.3 . . ?
N11 C12 H12 108.3 . . ?
C13 C12 H12 108.3 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 120.0 . . ?
C15 C14 C12 117.3(4) . . ?
C19 C14 C12 122.4(4) . . ?
C14 C15 C16 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C14 120.0 . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?

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
C3 C1 C4 C5 -38.9(9) . . . . ?
C2 C1 C4 C5 -166.2(6) . . . . ?
C9 C1 C4 C5 82.0(6) . . . . ?
C3 C1 C4 C10 -149.6(7) . . . . ?
C2 C1 C4 C10 83.1(7) . . . . ?
C9 C1 C4 C10 -28.7(5) . . . . ?
C10 C4 C5 C6 -85.1(7) . . . . ?
C1 C4 C5 C6 178.6(6) . . . . ?
C10 C4 C5 C7 37.0(7) . . . . ?
C1 C4 C5 C7 -59.2(7) . . . . ?
C6 C5 C7 N11 -90.5(7) . . . . ?
C4 C5 C7 N11 148.7(5) . . . . ?
C6 C5 C7 C8 144.0(7) . . . . ?
C4 C5 C7 C8 23.2(8) . . . . ?
N11 C7 C8 C9 -152.8(6) . . . . ?
C5 C7 C8 C9 -25.5(9) . . . . ?
C7 C8 C9 C1 62.7(8) . . . . ?
C7 C8 C9 C10 -32.8(8) . . . . ?
C3 C1 C9 C8 36.5(9) . . . . ?
C2 C1 C9 C8 165.7(6) . . . . ?
C4 C1 C9 C8 -82.1(6) . . . . ?
C3 C1 C9 C10 147.2(7) . . . . ?
C2 C1 C9 C10 -83.5(7) . . . . ?
C4 C1 C9 C10 28.6(5) . . . . ?
C5 C4 C10 C9 -86.1(6) . . . . ?
C1 C4 C10 C9 28.5(5) . . . . ?
C8 C9 C10 C4 83.3(6) . . . . ?
C1 C9 C10 C4 -28.6(5) . . . . ?
C8 C7 N11 C12 -154.5(5) . . . . ?
C5 C7 N11 C12 77.8(6) . . . . ?
C7 N11 C12 C14 52.3(7) . . . . ?
C7 N11 C12 C13 175.0(5) . . . . ?
N11 C12 C14 C15 -147.0(4) . . . . ?
C13 C12 C14 C15 91.8(5) . . . . ?
N11 C12 C14 C19 39.3(6) . . . . ?
C13 C12 C14 C19 -81.9(5) . . . . ?
C19 C14 C15 C16 0.0 . . . . ?
C12 C14 C15 C16 -173.9(5) . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C17 C18 C19 C14 0.0 . . . . ?
C15 C14 C19 C18 0.0 . . . . ?
C12 C14 C19 C18 173.5(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# -----------------------
#
# D       H       A       D-H         H...A       D...A      D-H...A   symm publ
# ------------------------------------------------------------------------------
N11 H11A Cl1 0.91 2.24 3.137(5) 166.7 2_655 yes
N11 H11A Cl1 0.91 2.24 3.137(5) 166.7 2_655 yes
N11 H11B Cl1 0.91 2.30 3.200(5) 168.6 . yes
N11 H11B Cl1 0.91 2.30 3.200(5) 168.6 . yes

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_DG185F2_HpinoSS
_database_code_depnum_ccdc_archive 'CCDC 2110273'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;Institut des Sciences Chimiques de Rennes
France
;
_audit_update_record             
;
2021-09-16 deposited with the CCDC.	2021-11-18 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 08/11/2010                                               #
#------------------------------------------------------------------------------#


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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C25 H30 N2 O3'
_chemical_formula_sum            'C25 H30 N2 O3'
_chemical_formula_weight         406.51
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration unk

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
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                   7.7346(6)
_cell_length_b                   14.3407(9)
_cell_length_c                   39.815(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4416.3(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6886
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      26.02
_cell_measurement_wavelength     0.71073


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0839875
_diffrn_orient_matrix_UB_21      0.0028289
_diffrn_orient_matrix_UB_31      0.0982069
_diffrn_orient_matrix_UB_12      -0.0367391
_diffrn_orient_matrix_UB_22      0.0511037
_diffrn_orient_matrix_UB_32      0.0299475
_diffrn_orient_matrix_UB_13      -0.0137518
_diffrn_orient_matrix_UB_23      -0.0170663
_diffrn_orient_matrix_UB_33      0.0122522


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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.130
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1744
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.851
_exptl_absorpt_correction_T_max  0.990

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

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

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.33
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_uneti/neti     0.0561
_diffrn_reflns_av_r_equivalents  0.0357
_diffrn_reflns_number            22543
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.926
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             9897
_reflns_number_gt                7802
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_max     0.948
_reflns_Friedel_fraction_full    0.959

_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.
;

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

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SIR97 (A. Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2020)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0441P)²+0.3169P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9897
_refine_ls_number_parameters     549
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1004
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.037

#------------------------------------------------------------------------------#
#               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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_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
N1 N 0.2763(3) 1.08743(16) 0.26513(6) 0.0358(5) Uani 1 1 d . . . . .
O3 O 0.3933(3) 1.13907(13) 0.27459(5) 0.0444(5) Uani 1 1 d . . . . .
O2 O 0.1757(3) 1.10690(14) 0.24227(5) 0.0499(5) Uani 1 1 d . . . . .
C4 C 0.2534(3) 0.99767(18) 0.28266(6) 0.0290(6) Uani 1 1 d . . . . .
C5 C 0.1292(3) 0.93662(18) 0.27070(6) 0.0313(6) Uani 1 1 d . . . . .
H5 H 0.065172 0.950730 0.250980 0.038 Uiso 1 1 calc R U . . .
C6 C 0.1005(3) 0.85465(18) 0.28810(6) 0.0306(6) Uani 1 1 d . . . . .
H6 H 0.014328 0.812484 0.280454 0.037 Uiso 1 1 calc R U . . .
C7 C 0.1963(3) 0.83307(17) 0.31670(6) 0.0274(6) Uani 1 1 d . . . . .
C8 C 0.3221(3) 0.89566(18) 0.32785(6) 0.0300(6) Uani 1 1 d . . . . .
H8 H 0.388622 0.881245 0.347220 0.036 Uiso 1 1 calc R U . . .
C9 C 0.3507(3) 0.97879(18) 0.31087(6) 0.0299(6) Uani 1 1 d . . . . .
H9 H 0.435530 1.021736 0.318513 0.036 Uiso 1 1 calc R U . . .
C10 C 0.1503(3) 0.74913(18) 0.33772(6) 0.0283(6) Uani 1 1 d . . . . .
O11 O 0.0144(2) 0.75176(12) 0.35408(4) 0.0345(4) Uani 1 1 d . . . . .
N12 N 0.2633(3) 0.67679(14) 0.33888(5) 0.0283(5) Uani 1 1 d . . . . .
C13 C 0.4106(3) 0.66987(18) 0.31486(7) 0.0305(6) Uani 1 1 d . . . . .
H13 H 0.390215 0.717398 0.296911 0.037 Uiso 1 1 calc R U . . .
C14 C 0.5824(3) 0.6948(2) 0.33177(8) 0.0431(7) Uani 1 1 d . . . . .
H14A H 0.579210 0.759846 0.339235 0.065 Uiso 1 1 calc R U . . .
H14B H 0.677158 0.686386 0.315710 0.065 Uiso 1 1 calc R U . . .
H14C H 0.600753 0.653936 0.351188 0.065 Uiso 1 1 calc R U . . .
C15 C 0.4110(3) 0.57475(18) 0.29782(7) 0.0314(6) Uani 1 1 d . . . . .
C16 C 0.3149(3) 0.56176(19) 0.26864(7) 0.0354(6) Uani 1 1 d . . . . .
H16 H 0.249579 0.612211 0.259813 0.042 Uiso 1 1 calc R U . . .
C17 C 0.3129(4) 0.4762(2) 0.25216(8) 0.0455(7) Uani 1 1 d . . . . .
H17 H 0.248679 0.469041 0.231987 0.055 Uiso 1 1 calc R U . . .
C18 C 0.4042(4) 0.4019(2) 0.26511(9) 0.0516(9) Uani 1 1 d . . . . .
H18 H 0.400565 0.342911 0.254301 0.062 Uiso 1 1 calc R U . . .
C19 C 0.5005(5) 0.4140(2) 0.29382(9) 0.0536(9) Uani 1 1 d . . . . .
H19 H 0.563490 0.362805 0.302734 0.064 Uiso 1 1 calc R U . . .
C20 C 0.5074(4) 0.4995(2) 0.30997(8) 0.0435(7) Uani 1 1 d . . . . .
H20 H 0.577830 0.507077 0.329329 0.052 Uiso 1 1 calc R U . . .
C21 C 0.2504(3) 0.60292(18) 0.36494(6) 0.0296(6) Uani 1 1 d . . . . .
H21 H 0.365372 0.571142 0.363977 0.036 Uiso 1 1 calc R U . . .
C22 C 0.2440(4) 0.6446(2) 0.40107(6) 0.0394(7) Uani 1 1 d . . . . .
H22A H 0.363199 0.649879 0.409910 0.047 Uiso 1 1 calc R U . . .
H22B H 0.194082 0.708089 0.400068 0.047 Uiso 1 1 calc R U . . .
C23 C 0.1371(4) 0.5853(2) 0.42493(7) 0.0435(7) Uani 1 1 d . . . . .
H23 H 0.136827 0.607161 0.448787 0.052 Uiso 1 1 calc R U . . .
C24 C -0.0441(4) 0.5725(2) 0.40923(7) 0.0438(7) Uani 1 1 d . . . . .
H24A H -0.080854 0.624246 0.394389 0.053 Uiso 1 1 calc R U . . .
H24B H -0.135735 0.555836 0.425521 0.053 Uiso 1 1 calc R U . . .
C25 C 0.0361(4) 0.48823(19) 0.39054(7) 0.0376(7) Uani 1 1 d . . . . .
H25 H -0.043477 0.433804 0.387818 0.045 Uiso 1 1 calc R U . . .
C26 C 0.1182(3) 0.52262(18) 0.35779(6) 0.0291(6) Uani 1 1 d . . . . .
H26 H 0.186672 0.469231 0.348609 0.035 Uiso 1 1 calc R U . . .
C27 C -0.0207(3) 0.54445(19) 0.33190(6) 0.0341(6) Uani 1 1 d . . . . .
H27A H -0.093361 0.489281 0.328466 0.051 Uiso 1 1 calc R U . . .
H27B H 0.034031 0.561906 0.310609 0.051 Uiso 1 1 calc R U . . .
H27C H -0.092281 0.596225 0.339947 0.051 Uiso 1 1 calc R U . . .
C28 C 0.1669(4) 0.4790(2) 0.42033(7) 0.0450(7) Uani 1 1 d . . . . .
C29 C 0.3480(4) 0.4416(2) 0.41408(8) 0.0559(9) Uani 1 1 d . . . . .
H29A H 0.395025 0.469611 0.393578 0.084 Uiso 1 1 calc R U . . .
H29B H 0.343173 0.373661 0.411460 0.084 Uiso 1 1 calc R U . . .
H29C H 0.422486 0.457271 0.433168 0.084 Uiso 1 1 calc R U . . .
C30 C 0.0869(6) 0.4228(2) 0.44944(8) 0.0644(10) Uani 1 1 d . . . . .
H30A H 0.088419 0.356233 0.443834 0.097 Uiso 1 1 calc R U . . .
H30B H -0.032627 0.443049 0.453045 0.097 Uiso 1 1 calc R U . . .
H30C H 0.154187 0.433263 0.469960 0.097 Uiso 1 1 calc R U . . .
N51 N 0.5118(4) -0.3132(2) 0.48972(8) 0.0590(8) Uani 1 1 d . . . . .
O52 O 0.4570(4) -0.2956(2) 0.51755(7) 0.0915(10) Uani 1 1 d . . . . .
O53 O 0.5338(6) -0.39189(19) 0.47924(8) 0.1117(12) Uani 1 1 d . . . . .
C54 C 0.5575(3) -0.23532(19) 0.46739(7) 0.0358(6) Uani 1 1 d . . . . .
C55 C 0.6409(4) -0.25460(19) 0.43763(7) 0.0378(6) Uani 1 1 d . . . . .
H55 H 0.663759 -0.317204 0.431219 0.045 Uiso 1 1 calc R U . . .
C56 C 0.6905(3) -0.18181(18) 0.41738(6) 0.0321(6) Uani 1 1 d . . . . .
H56 H 0.748651 -0.193771 0.396807 0.038 Uiso 1 1 calc R U . . .
C57 C 0.6555(3) -0.09058(17) 0.42707(6) 0.0255(5) Uani 1 1 d . . . . .
C58 C 0.5684(3) -0.07324(18) 0.45686(6) 0.0303(6) Uani 1 1 d . . . . .
H58 H 0.542796 -0.010863 0.463173 0.036 Uiso 1 1 calc R U . . .
C59 C 0.5186(3) -0.14577(19) 0.47736(7) 0.0361(7) Uani 1 1 d . . . . .
H59 H 0.459058 -0.134361 0.497822 0.043 Uiso 1 1 calc R U . . .
C60 C 0.7036(3) -0.01122(17) 0.40404(6) 0.0264(5) Uani 1 1 d . . . . .
O51 O 0.5947(2) 0.01622(13) 0.38365(4) 0.0353(4) Uani 1 1 d . . . . .
N62 N 0.8640(2) 0.02499(13) 0.40701(5) 0.0229(4) Uani 1 1 d . . . . .
C63 C 0.9956(3) -0.01636(16) 0.43005(6) 0.0237(5) Uani 1 1 d . . . . .
H63 H 0.931626 -0.058537 0.445726 0.028 Uiso 1 1 calc R U . . .
C64 C 1.1235(3) -0.07723(17) 0.41094(7) 0.0316(6) Uani 1 1 d . . . . .
H64A H 1.060375 -0.124787 0.398215 0.047 Uiso 1 1 calc R U . . .
H64B H 1.201865 -0.107655 0.426886 0.047 Uiso 1 1 calc R U . . .
H64C H 1.190633 -0.038427 0.395437 0.047 Uiso 1 1 calc R U . . .
C65 C 1.0810(3) 0.05785(16) 0.45160(6) 0.0224(5) Uani 1 1 d . . . . .
C66 C 1.2396(3) 0.09808(17) 0.44361(6) 0.0285(6) Uani 1 1 d . . . . .
H66 H 1.296433 0.081168 0.423348 0.034 Uiso 1 1 calc R U . . .
C67 C 1.3156(3) 0.16275(18) 0.46501(7) 0.0348(6) Uani 1 1 d . . . . .
H67 H 1.422613 0.190705 0.459033 0.042 Uiso 1 1 calc R U . . .
C68 C 1.2369(4) 0.18662(18) 0.49485(6) 0.0341(6) Uani 1 1 d . . . . .
H68 H 1.290098 0.230052 0.509603 0.041 Uiso 1 1 calc R U . . .
C69 C 1.0802(4) 0.14689(17) 0.50309(7) 0.0329(6) Uani 1 1 d . . . . .
H69 H 1.025163 0.162965 0.523623 0.039 Uiso 1 1 calc R U . . .
C70 C 1.0026(3) 0.08352(17) 0.48150(6) 0.0276(5) Uani 1 1 d . . . . .
H70 H 0.893833 0.057277 0.487318 0.033 Uiso 1 1 calc R U . . .
C71 C 0.9298(3) 0.09409(16) 0.38244(5) 0.0234(5) Uani 1 1 d . . . . .
H71 H 1.055988 0.098328 0.387726 0.028 Uiso 1 1 calc R U . . .
C72 C 0.9260(3) 0.05541(17) 0.34610(6) 0.0260(5) Uani 1 1 d . . . . .
H72A H 1.036571 0.023270 0.341314 0.031 Uiso 1 1 calc R U . . .
H72B H 0.831756 0.009032 0.344096 0.031 Uiso 1 1 calc R U . . .
C73 C 0.8984(3) 0.13229(16) 0.32038(6) 0.0266(5) Uani 1 1 d . . . . .
H73 H 0.906634 0.111872 0.296418 0.032 Uiso 1 1 calc R U . . .
C74 C 0.7289(3) 0.18264(18) 0.32971(6) 0.0309(6) Uani 1 1 d . . . . .
H74A H 0.644109 0.143135 0.341743 0.037 Uiso 1 1 calc R U . . .
H74B H 0.674139 0.216665 0.310868 0.037 Uiso 1 1 calc R U . . .
C75 C 0.8418(3) 0.24437(17) 0.35293(6) 0.0274(5) Uani 1 1 d . . . . .
H75 H 0.805828 0.311271 0.354021 0.033 Uiso 1 1 calc R U . . .
C76 C 0.8633(3) 0.19697(16) 0.38719(6) 0.0262(5) Uani 1 1 d . . . . .
H76 H 0.958048 0.231314 0.398974 0.031 Uiso 1 1 calc R U . . .
C77 C 0.7014(4) 0.20968(19) 0.40875(7) 0.0367(7) Uani 1 1 d . . . . .
H77A H 0.683645 0.276178 0.413242 0.055 Uiso 1 1 calc R U . . .
H77B H 0.715979 0.176311 0.430042 0.055 Uiso 1 1 calc R U . . .
H77C H 0.600858 0.184686 0.396780 0.055 Uiso 1 1 calc R U . . .
C78 C 0.9973(3) 0.22431(17) 0.32882(6) 0.0282(6) Uani 1 1 d . . . . .
C79 C 0.9969(4) 0.28994(18) 0.29849(6) 0.0391(7) Uani 1 1 d . . . . .
H79A H 1.036621 0.351877 0.305453 0.059 Uiso 1 1 calc R U . . .
H79B H 0.879314 0.294582 0.289458 0.059 Uiso 1 1 calc R U . . .
H79C H 1.074365 0.265367 0.281144 0.059 Uiso 1 1 calc R U . . .
C80 C 1.1814(3) 0.22254(19) 0.34293(6) 0.0339(6) Uani 1 1 d . . . . .
H80A H 1.263730 0.212297 0.324586 0.051 Uiso 1 1 calc R U . . .
H80B H 1.191769 0.171974 0.359359 0.051 Uiso 1 1 calc R U . . .
H80C H 1.206548 0.282235 0.353871 0.051 Uiso 1 1 calc R U . . .



#------------------------------------------------------------------------------#
#                              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
N1 O3 1.228(3) . ?
N1 O2 1.230(3) . ?
N1 C4 1.475(3) . ?
C4 C9 1.379(3) . ?
C4 C5 1.384(4) . ?
C5 C6 1.382(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.396(3) . ?
C7 C10 1.509(4) . ?
C8 C9 1.388(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 O11 1.237(3) . ?
C10 N12 1.357(3) . ?
N12 C21 1.486(3) . ?
N12 C13 1.491(3) . ?
C13 C15 1.524(4) . ?
C13 C14 1.532(4) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.391(4) . ?
C15 C20 1.398(4) . ?
C16 C17 1.391(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.378(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.376(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.386(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.559(4) . ?
C21 C26 1.566(3) . ?
C21 H21 1.0000 . ?
C22 C23 1.519(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.545(4) . ?
C23 C28 1.553(4) . ?
C23 H23 1.0000 . ?
C24 C25 1.549(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.532(4) . ?
C25 C28 1.565(4) . ?
C25 H25 1.0000 . ?
C26 C27 1.522(3) . ?
C26 H26 1.0000 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.521(5) . ?
C28 C30 1.542(4) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
N51 O52 1.213(4) . ?
N51 O53 1.215(4) . ?
N51 C54 1.471(4) . ?
C54 C55 1.377(4) . ?
C54 C59 1.377(4) . ?
C55 C56 1.374(4) . ?
C55 H55 0.9500 . ?
C56 C57 1.391(4) . ?
C56 H56 0.9500 . ?
C57 C58 1.387(3) . ?
C57 C60 1.508(3) . ?
C58 C59 1.377(4) . ?
C58 H58 0.9500 . ?
C59 H59 0.9500 . ?
C60 O51 1.234(3) . ?
C60 N62 1.350(3) . ?
N62 C71 1.483(3) . ?
N62 C63 1.493(3) . ?
C63 C65 1.518(3) . ?
C63 C64 1.523(3) . ?
C63 H63 1.0000 . ?
C64 H64A 0.9800 . ?
C64 H64B 0.9800 . ?
C64 H64C 0.9800 . ?
C65 C70 1.386(3) . ?
C65 C66 1.393(3) . ?
C66 C67 1.390(3) . ?
C66 H66 0.9500 . ?
C67 C68 1.378(4) . ?
C67 H67 0.9500 . ?
C68 C69 1.379(4) . ?
C68 H68 0.9500 . ?
C69 C70 1.387(3) . ?
C69 H69 0.9500 . ?
C70 H70 0.9500 . ?
C71 C72 1.550(3) . ?
C71 C76 1.574(3) . ?
C71 H71 1.0000 . ?
C72 C73 1.520(3) . ?
C72 H72A 0.9900 . ?
C72 H72B 0.9900 . ?
C73 C74 1.542(3) . ?
C73 C78 1.562(3) . ?
C73 H73 1.0000 . ?
C74 C75 1.550(3) . ?
C74 H74A 0.9900 . ?
C74 H74B 0.9900 . ?
C75 C76 1.533(3) . ?
C75 C78 1.565(3) . ?
C75 H75 1.0000 . ?
C76 C77 1.529(3) . ?
C76 H76 1.0000 . ?
C77 H77A 0.9800 . ?
C77 H77B 0.9800 . ?
C77 H77C 0.9800 . ?
C78 C80 1.531(4) . ?
C78 C79 1.531(3) . ?
C79 H79A 0.9800 . ?
C79 H79B 0.9800 . ?
C79 H79C 0.9800 . ?
C80 H80A 0.9800 . ?
C80 H80B 0.9800 . ?
C80 H80C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 N1 O2 123.8(2) . . ?
O3 N1 C4 118.0(2) . . ?
O2 N1 C4 118.2(2) . . ?
C9 C4 C5 122.3(2) . . ?
C9 C4 N1 119.4(2) . . ?
C5 C4 N1 118.2(2) . . ?
C6 C5 C4 118.5(2) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C5 C6 C7 120.9(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C8 119.2(2) . . ?
C6 C7 C10 120.3(2) . . ?
C8 C7 C10 120.1(2) . . ?
C9 C8 C7 120.6(2) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C4 C9 C8 118.6(2) . . ?
C4 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
O11 C10 N12 123.5(2) . . ?
O11 C10 C7 117.9(2) . . ?
N12 C10 C7 118.5(2) . . ?
C10 N12 C21 121.7(2) . . ?
C10 N12 C13 121.4(2) . . ?
C21 N12 C13 116.85(19) . . ?
N12 C13 C15 110.3(2) . . ?
N12 C13 C14 111.4(2) . . ?
C15 C13 C14 113.7(2) . . ?
N12 C13 H13 107.0 . . ?
C15 C13 H13 107.0 . . ?
C14 C13 H13 107.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 118.1(3) . . ?
C16 C15 C13 119.4(2) . . ?
C20 C15 C13 122.5(3) . . ?
C17 C16 C15 121.2(3) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C18 C17 C16 120.0(3) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 119.4(3) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 121.2(3) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C19 C20 C15 120.1(3) . . ?
C19 C20 H20 119.9 . . ?
C15 C20 H20 119.9 . . ?
N12 C21 C22 111.9(2) . . ?
N12 C21 C26 116.16(19) . . ?
C22 C21 C26 115.4(2) . . ?
N12 C21 H21 103.8 . . ?
C22 C21 H21 103.8 . . ?
C26 C21 H21 103.8 . . ?
C23 C22 C21 112.3(2) . . ?
C23 C22 H22A 109.1 . . ?
C21 C22 H22A 109.1 . . ?
C23 C22 H22B 109.1 . . ?
C21 C22 H22B 109.1 . . ?
H22A C22 H22B 107.9 . . ?
C22 C23 C24 107.9(2) . . ?
C22 C23 C28 113.2(2) . . ?
C24 C23 C28 88.3(2) . . ?
C22 C23 H23 114.8 . . ?
C24 C23 H23 114.8 . . ?
C28 C23 H23 114.8 . . ?
C23 C24 C25 85.6(2) . . ?
C23 C24 H24A 114.4 . . ?
C25 C24 H24A 114.4 . . ?
C23 C24 H24B 114.4 . . ?
C25 C24 H24B 114.4 . . ?
H24A C24 H24B 111.5 . . ?
C26 C25 C24 108.9(2) . . ?
C26 C25 C28 113.9(2) . . ?
C24 C25 C28 87.7(2) . . ?
C26 C25 H25 114.5 . . ?
C24 C25 H25 114.5 . . ?
C28 C25 H25 114.5 . . ?
C27 C26 C25 110.5(2) . . ?
C27 C26 C21 115.7(2) . . ?
C25 C26 C21 110.6(2) . . ?
C27 C26 H26 106.5 . . ?
C25 C26 H26 106.5 . . ?
C21 C26 H26 106.5 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 C30 107.9(3) . . ?
C29 C28 C23 120.2(3) . . ?
C30 C28 C23 111.4(3) . . ?
C29 C28 C25 120.1(2) . . ?
C30 C28 C25 110.8(3) . . ?
C23 C28 C25 84.9(2) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O52 N51 O53 123.8(3) . . ?
O52 N51 C54 118.6(3) . . ?
O53 N51 C54 117.6(3) . . ?
C55 C54 C59 122.5(2) . . ?
C55 C54 N51 118.7(3) . . ?
C59 C54 N51 118.8(3) . . ?
C56 C55 C54 118.9(3) . . ?
C56 C55 H55 120.5 . . ?
C54 C55 H55 120.5 . . ?
C55 C56 C57 119.8(2) . . ?
C55 C56 H56 120.1 . . ?
C57 C56 H56 120.1 . . ?
C58 C57 C56 120.0(2) . . ?
C58 C57 C60 120.3(2) . . ?
C56 C57 C60 119.6(2) . . ?
C59 C58 C57 120.5(2) . . ?
C59 C58 H58 119.8 . . ?
C57 C58 H58 119.8 . . ?
C58 C59 C54 118.2(2) . . ?
C58 C59 H59 120.9 . . ?
C54 C59 H59 120.9 . . ?
O51 C60 N62 124.2(2) . . ?
O51 C60 C57 118.2(2) . . ?
N62 C60 C57 117.6(2) . . ?
C60 N62 C71 121.00(19) . . ?
C60 N62 C63 121.83(19) . . ?
C71 N62 C63 115.90(18) . . ?
N62 C63 C65 111.43(19) . . ?
N62 C63 C64 111.32(19) . . ?
C65 C63 C64 113.7(2) . . ?
N62 C63 H63 106.6 . . ?
C65 C63 H63 106.6 . . ?
C64 C63 H63 106.6 . . ?
C63 C64 H64A 109.5 . . ?
C63 C64 H64B 109.5 . . ?
H64A C64 H64B 109.5 . . ?
C63 C64 H64C 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?
C70 C65 C66 118.2(2) . . ?
C70 C65 C63 118.8(2) . . ?
C66 C65 C63 123.0(2) . . ?
C67 C66 C65 120.6(2) . . ?
C67 C66 H66 119.7 . . ?
C65 C66 H66 119.7 . . ?
C68 C67 C66 120.5(2) . . ?
C68 C67 H67 119.7 . . ?
C66 C67 H67 119.7 . . ?
C67 C68 C69 119.4(2) . . ?
C67 C68 H68 120.3 . . ?
C69 C68 H68 120.3 . . ?
C68 C69 C70 120.2(2) . . ?
C68 C69 H69 119.9 . . ?
C70 C69 H69 119.9 . . ?
C65 C70 C69 121.1(2) . . ?
C65 C70 H70 119.4 . . ?
C69 C70 H70 119.4 . . ?
N62 C71 C72 111.73(19) . . ?
N62 C71 C76 115.77(18) . . ?
C72 C71 C76 116.19(19) . . ?
N62 C71 H71 103.7 . . ?
C72 C71 H71 103.7 . . ?
C76 C71 H71 103.7 . . ?
C73 C72 C71 111.84(19) . . ?
C73 C72 H72A 109.2 . . ?
C71 C72 H72A 109.2 . . ?
C73 C72 H72B 109.2 . . ?
C71 C72 H72B 109.2 . . ?
H72A C72 H72B 107.9 . . ?
C72 C73 C74 107.3(2) . . ?
C72 C73 C78 113.52(19) . . ?
C74 C73 C78 88.24(18) . . ?
C72 C73 H73 114.9 . . ?
C74 C73 H73 114.9 . . ?
C78 C73 H73 114.9 . . ?
C73 C74 C75 86.09(18) . . ?
C73 C74 H74A 114.3 . . ?
C75 C74 H74A 114.3 . . ?
C73 C74 H74B 114.3 . . ?
C75 C74 H74B 114.3 . . ?
H74A C74 H74B 111.4 . . ?
C76 C75 C74 109.8(2) . . ?
C76 C75 C78 112.4(2) . . ?
C74 C75 C78 87.84(18) . . ?
C76 C75 H75 114.6 . . ?
C74 C75 H75 114.6 . . ?
C78 C75 H75 114.6 . . ?
C77 C76 C75 111.0(2) . . ?
C77 C76 C71 116.6(2) . . ?
C75 C76 C71 110.12(18) . . ?
C77 C76 H76 106.2 . . ?
C75 C76 H76 106.2 . . ?
C71 C76 H76 106.2 . . ?
C76 C77 H77A 109.5 . . ?
C76 C77 H77B 109.5 . . ?
H77A C77 H77B 109.5 . . ?
C76 C77 H77C 109.5 . . ?
H77A C77 H77C 109.5 . . ?
H77B C77 H77C 109.5 . . ?
C80 C78 C79 107.6(2) . . ?
C80 C78 C73 121.4(2) . . ?
C79 C78 C73 110.4(2) . . ?
C80 C78 C75 119.5(2) . . ?
C79 C78 C75 111.7(2) . . ?
C73 C78 C75 84.88(18) . . ?
C78 C79 H79A 109.5 . . ?
C78 C79 H79B 109.5 . . ?
H79A C79 H79B 109.5 . . ?
C78 C79 H79C 109.5 . . ?
H79A C79 H79C 109.5 . . ?
H79B C79 H79C 109.5 . . ?
C78 C80 H80A 109.5 . . ?
C78 C80 H80B 109.5 . . ?
H80A C80 H80B 109.5 . . ?
C78 C80 H80C 109.5 . . ?
H80A C80 H80C 109.5 . . ?
H80B C80 H80C 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
O3 N1 C4 C9 6.5(3) . . . . ?
O2 N1 C4 C9 -172.4(2) . . . . ?
O3 N1 C4 C5 -175.8(2) . . . . ?
O2 N1 C4 C5 5.3(3) . . . . ?
C9 C4 C5 C6 1.1(4) . . . . ?
N1 C4 C5 C6 -176.5(2) . . . . ?
C4 C5 C6 C7 -1.1(4) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C5 C6 C7 C10 172.9(2) . . . . ?
C6 C7 C8 C9 0.5(3) . . . . ?
C10 C7 C8 C9 -172.1(2) . . . . ?
C5 C4 C9 C8 -0.3(4) . . . . ?
N1 C4 C9 C8 177.3(2) . . . . ?
C7 C8 C9 C4 -0.5(4) . . . . ?
C6 C7 C10 O11 -69.7(3) . . . . ?
C8 C7 C10 O11 102.9(3) . . . . ?
C6 C7 C10 N12 113.2(3) . . . . ?
C8 C7 C10 N12 -74.2(3) . . . . ?
O11 C10 N12 C21 -12.2(4) . . . . ?
C7 C10 N12 C21 164.7(2) . . . . ?
O11 C10 N12 C13 170.3(2) . . . . ?
C7 C10 N12 C13 -12.8(3) . . . . ?
C10 N12 C13 C15 -127.7(2) . . . . ?
C21 N12 C13 C15 54.7(3) . . . . ?
C10 N12 C13 C14 105.0(3) . . . . ?
C21 N12 C13 C14 -72.6(3) . . . . ?
N12 C13 C15 C16 87.6(3) . . . . ?
C14 C13 C15 C16 -146.3(2) . . . . ?
N12 C13 C15 C20 -93.7(3) . . . . ?
C14 C13 C15 C20 32.3(4) . . . . ?
C20 C15 C16 C17 0.7(4) . . . . ?
C13 C15 C16 C17 179.5(2) . . . . ?
C15 C16 C17 C18 1.4(4) . . . . ?
C16 C17 C18 C19 -1.8(4) . . . . ?
C17 C18 C19 C20 0.0(4) . . . . ?
C18 C19 C20 C15 2.2(4) . . . . ?
C16 C15 C20 C19 -2.5(4) . . . . ?
C13 C15 C20 C19 178.8(3) . . . . ?
C10 N12 C21 C22 -52.7(3) . . . . ?
C13 N12 C21 C22 124.9(2) . . . . ?
C10 N12 C21 C26 82.8(3) . . . . ?
C13 N12 C21 C26 -99.7(2) . . . . ?
N12 C21 C22 C23 148.3(2) . . . . ?
C26 C21 C22 C23 12.4(3) . . . . ?
C21 C22 C23 C24 -54.9(3) . . . . ?
C21 C22 C23 C28 41.2(3) . . . . ?
C22 C23 C24 C25 86.5(2) . . . . ?
C28 C23 C24 C25 -27.4(2) . . . . ?
C23 C24 C25 C26 -87.3(2) . . . . ?
C23 C24 C25 C28 27.2(2) . . . . ?
C24 C25 C26 C27 -74.9(3) . . . . ?
C28 C25 C26 C27 -170.9(2) . . . . ?
C24 C25 C26 C21 54.5(3) . . . . ?
C28 C25 C26 C21 -41.5(3) . . . . ?
N12 C21 C26 C27 -19.4(3) . . . . ?
C22 C21 C26 C27 114.5(3) . . . . ?
N12 C21 C26 C25 -146.0(2) . . . . ?
C22 C21 C26 C25 -12.0(3) . . . . ?
C22 C23 C28 C29 40.4(4) . . . . ?
C24 C23 C28 C29 149.2(3) . . . . ?
C22 C23 C28 C30 168.1(3) . . . . ?
C24 C23 C28 C30 -83.1(3) . . . . ?
C22 C23 C28 C25 -81.6(3) . . . . ?
C24 C23 C28 C25 27.2(2) . . . . ?
C26 C25 C28 C29 -39.5(4) . . . . ?
C24 C25 C28 C29 -149.2(3) . . . . ?
C26 C25 C28 C30 -166.4(3) . . . . ?
C24 C25 C28 C30 83.9(3) . . . . ?
C26 C25 C28 C23 82.6(3) . . . . ?
C24 C25 C28 C23 -27.1(2) . . . . ?
O52 N51 C54 C55 171.4(3) . . . . ?
O53 N51 C54 C55 -7.5(4) . . . . ?
O52 N51 C54 C59 -7.2(4) . . . . ?
O53 N51 C54 C59 173.9(3) . . . . ?
C59 C54 C55 C56 1.3(4) . . . . ?
N51 C54 C55 C56 -177.2(2) . . . . ?
C54 C55 C56 C57 -0.3(4) . . . . ?
C55 C56 C57 C58 -1.0(4) . . . . ?
C55 C56 C57 C60 -177.4(2) . . . . ?
C56 C57 C58 C59 1.2(4) . . . . ?
C60 C57 C58 C59 177.6(2) . . . . ?
C57 C58 C59 C54 -0.1(4) . . . . ?
C55 C54 C59 C58 -1.2(4) . . . . ?
N51 C54 C59 C58 177.4(2) . . . . ?
C58 C57 C60 O51 -85.1(3) . . . . ?
C56 C57 C60 O51 91.3(3) . . . . ?
C58 C57 C60 N62 95.2(3) . . . . ?
C56 C57 C60 N62 -88.4(3) . . . . ?
O51 C60 N62 C71 -8.0(4) . . . . ?
C57 C60 N62 C71 171.7(2) . . . . ?
O51 C60 N62 C63 -174.6(2) . . . . ?
C57 C60 N62 C63 5.1(3) . . . . ?
C60 N62 C63 C65 -131.7(2) . . . . ?
C71 N62 C63 C65 61.1(3) . . . . ?
C60 N62 C63 C64 100.3(3) . . . . ?
C71 N62 C63 C64 -66.9(3) . . . . ?
N62 C63 C65 C70 86.4(2) . . . . ?
C64 C63 C65 C70 -146.9(2) . . . . ?
N62 C63 C65 C66 -97.1(3) . . . . ?
C64 C63 C65 C66 29.6(3) . . . . ?
C70 C65 C66 C67 -0.6(3) . . . . ?
C63 C65 C66 C67 -177.1(2) . . . . ?
C65 C66 C67 C68 1.4(4) . . . . ?
C66 C67 C68 C69 -1.1(4) . . . . ?
C67 C68 C69 C70 0.0(4) . . . . ?
C66 C65 C70 C69 -0.5(3) . . . . ?
C63 C65 C70 C69 176.1(2) . . . . ?
C68 C69 C70 C65 0.9(4) . . . . ?
C60 N62 C71 C72 -57.5(3) . . . . ?
C63 N62 C71 C72 109.8(2) . . . . ?
C60 N62 C71 C76 78.5(3) . . . . ?
C63 N62 C71 C76 -114.2(2) . . . . ?
N62 C71 C72 C73 149.6(2) . . . . ?
C76 C71 C72 C73 13.7(3) . . . . ?
C71 C72 C73 C74 -56.7(3) . . . . ?
C71 C72 C73 C78 39.0(3) . . . . ?
C72 C73 C74 C75 87.2(2) . . . . ?
C78 C73 C74 C75 -26.91(17) . . . . ?
C73 C74 C75 C76 -86.2(2) . . . . ?
C73 C74 C75 C78 26.85(17) . . . . ?
C74 C75 C76 C77 -78.2(2) . . . . ?
C78 C75 C76 C77 -174.2(2) . . . . ?
C74 C75 C76 C71 52.4(3) . . . . ?
C78 C75 C76 C71 -43.6(3) . . . . ?
N62 C71 C76 C77 -17.9(3) . . . . ?
C72 C71 C76 C77 116.2(2) . . . . ?
N62 C71 C76 C75 -145.5(2) . . . . ?
C72 C71 C76 C75 -11.4(3) . . . . ?
C72 C73 C78 C80 40.2(3) . . . . ?
C74 C73 C78 C80 148.3(2) . . . . ?
C72 C73 C78 C79 167.4(2) . . . . ?
C74 C73 C78 C79 -84.5(2) . . . . ?
C72 C73 C78 C75 -81.4(2) . . . . ?
C74 C73 C78 C75 26.67(17) . . . . ?
C76 C75 C78 C80 -39.4(3) . . . . ?
C74 C75 C78 C80 -149.9(2) . . . . ?
C76 C75 C78 C79 -166.1(2) . . . . ?
C74 C75 C78 C79 83.4(2) . . . . ?
C76 C75 C78 C73 84.0(2) . . . . ?
C74 C75 C78 C73 -26.53(17) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_D9_179F2_HpinoSR
_database_code_depnum_ccdc_archive 'CCDC 2110272'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;Institut des Sciences Chimiques de Rennes
France
;
_audit_update_record             
;
2021-09-16 deposited with the CCDC.	2021-11-18 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 27/09/2010                                               #
#------------------------------------------------------------------------------#


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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H28 N, Cl'
_chemical_formula_sum            'C18 H28 Cl N'
_chemical_formula_weight         293.86
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration rm/ad/rmad/syn/unk/.

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

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

_cell_length_a                   11.2823(3)
_cell_length_b                   7.3708(2)
_cell_length_c                   11.7289(3)
_cell_angle_alpha                90
_cell_angle_beta                 118.3930(10)
_cell_angle_gamma                90
_cell_volume                     858.04(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9515
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      27.49
_cell_measurement_wavelength     0.71073


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.0508560
_diffrn_orient_matrix_UB_21      0.0381006
_diffrn_orient_matrix_UB_31      0.0781890
_diffrn_orient_matrix_UB_12      0.0979761
_diffrn_orient_matrix_UB_22      -0.0417264
_diffrn_orient_matrix_UB_32      0.0840588
_diffrn_orient_matrix_UB_13      0.0170636
_diffrn_orient_matrix_UB_23      0.0918727
_diffrn_orient_matrix_UB_33      0.0257165


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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             320
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.791
_exptl_absorpt_correction_T_max  0.983

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

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

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.33
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_uneti/neti     0.0261
_diffrn_reflns_av_r_equivalents  0.0317
_diffrn_reflns_number            13935
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.397
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             3854
_reflns_number_gt                3724
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_max     0.963
_reflns_Friedel_fraction_full    0.992

_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.
;

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

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SIR97 (A. Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2020)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0413P)²+0.0918P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3854
_refine_ls_number_parameters     185
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0717
_refine_ls_wR_factor_gt          0.0705
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
Flack x determined using 1613 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.033(16)

#------------------------------------------------------------------------------#
#               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 0.0000 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'
Cl Cl 0.1484 0.1585 '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_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
C1 C 0.63594(16) 0.8480(3) -0.08739(15) 0.0288(4) Uani 1 1 d . . . . .
H1A H 0.653612 0.970075 -0.108772 0.043 Uiso 1 1 calc R U . . .
H1B H 0.540186 0.836488 -0.112108 0.043 Uiso 1 1 calc R U . . .
H1C H 0.659649 0.757960 -0.134680 0.043 Uiso 1 1 calc R U . . .
C2 C 0.72083(16) 0.8157(3) 0.05844(15) 0.0227(3) Uani 1 1 d . . . . .
H2 H 0.707309 0.687197 0.077054 0.027 Uiso 1 1 calc R U . . .
C3 C 0.86948(15) 0.8443(3) 0.10494(15) 0.0255(3) Uani 1 1 d . . . . .
C4 C 0.9568(2) 0.6961(3) 0.15027(19) 0.0363(5) Uani 1 1 d . . . . .
H4 H 0.924347 0.580610 0.158760 0.044 Uiso 1 1 calc R U . . .
C5 C 1.0926(2) 0.7189(4) 0.1831(2) 0.0479(6) Uani 1 1 d . . . . .
H5 H 1.152422 0.618498 0.214177 0.058 Uiso 1 1 calc R U . . .
C6 C 1.1399(2) 0.8864(4) 0.1707(2) 0.0493(7) Uani 1 1 d . . . . .
H6 H 1.231774 0.900164 0.191654 0.059 Uiso 1 1 calc R U . . .
C7 C 1.0546(2) 1.0335(4) 0.1282(2) 0.0432(5) Uani 1 1 d . . . . .
H7 H 1.088136 1.148988 0.121395 0.052 Uiso 1 1 calc R U . . .
C8 C 0.91897(19) 1.0137(3) 0.09492(18) 0.0316(4) Uani 1 1 d . . . . .
H8 H 0.860345 1.115455 0.065455 0.038 Uiso 1 1 calc R U . . .
N9 N 0.66955(14) 0.93921(19) 0.12902(13) 0.0197(3) Uani 1 1 d . . . . .
H9A H 0.672300 1.055737 0.104752 0.024 Uiso 1 1 calc R U . . .
H9B H 0.581759 0.911392 0.102840 0.024 Uiso 1 1 calc R U . . .
C10 C 0.74636(17) 0.9287(2) 0.27501(15) 0.0208(3) Uani 1 1 d . . . . .
H10 H 0.840227 0.970823 0.301869 0.025 Uiso 1 1 calc R U . . .
C11 C 0.68561(19) 1.0616(2) 0.33574(16) 0.0238(4) Uani 1 1 d . . . . .
H11 H 0.585464 1.062861 0.280622 0.029 Uiso 1 1 calc R U . . .
C12 C 0.7385(3) 1.2540(3) 0.3425(2) 0.0387(5) Uani 1 1 d . . . . .
H12A H 0.693875 1.336301 0.375715 0.058 Uiso 1 1 calc R U . . .
H12B H 0.719766 1.293083 0.255652 0.058 Uiso 1 1 calc R U . . .
H12C H 0.835990 1.256154 0.400497 0.058 Uiso 1 1 calc R U . . .
C13 C 0.71920(19) 0.9951(3) 0.47202(16) 0.0273(4) Uani 1 1 d . . . . .
H13 H 0.707034 1.087792 0.527831 0.033 Uiso 1 1 calc R U . . .
C14 C 0.8592(2) 0.9008(3) 0.53493(18) 0.0319(4) Uani 1 1 d . . . . .
H14A H 0.902898 0.892324 0.630606 0.038 Uiso 1 1 calc R U . . .
H14B H 0.922075 0.948014 0.505276 0.038 Uiso 1 1 calc R U . . .
C15 C 0.7811(2) 0.7270(3) 0.46268(17) 0.0283(4) Uani 1 1 d . . . . .
H15 H 0.817185 0.610271 0.510157 0.034 Uiso 1 1 calc R U . . .
C16 C 0.7567(2) 0.7305(2) 0.32202(18) 0.0267(4) Uani 1 1 d . . . . .
H16A H 0.672325 0.664920 0.265336 0.032 Uiso 1 1 calc R U . . .
H16B H 0.831860 0.668452 0.316870 0.032 Uiso 1 1 calc R U . . .
C17 C 0.65644(19) 0.8058(3) 0.46984(16) 0.0280(4) Uani 1 1 d . . . . .
C18 C 0.5155(2) 0.7609(3) 0.3626(2) 0.0385(5) Uani 1 1 d . . . . .
H18A H 0.499679 0.630114 0.362496 0.058 Uiso 1 1 calc R U . . .
H18B H 0.507399 0.796664 0.278737 0.058 Uiso 1 1 calc R U . . .
H18C H 0.448821 0.826877 0.377638 0.058 Uiso 1 1 calc R U . . .
C19 C 0.6603(3) 0.7633(3) 0.5999(2) 0.0420(5) Uani 1 1 d . . . . .
H19A H 0.591814 0.835759 0.608021 0.063 Uiso 1 1 calc R U . . .
H19B H 0.749542 0.792999 0.671206 0.063 Uiso 1 1 calc R U . . .
H19C H 0.641894 0.634047 0.603500 0.063 Uiso 1 1 calc R U . . .
Cl1 Cl 0.36505(3) 0.83468(5) 0.00404(4) 0.02569(11) Uani 1 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
C1 C2 1.530(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.511(2) . ?
C2 N9 1.518(2) . ?
C2 H2 1.0000 . ?
C3 C8 1.395(3) . ?
C3 C4 1.396(3) . ?
C4 C5 1.401(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.377(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.395(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
N9 C10 1.509(2) . ?
N9 H9A 0.9100 . ?
N9 H9B 0.9100 . ?
C10 C16 1.546(2) . ?
C10 C11 1.550(2) . ?
C10 H10 1.0000 . ?
C11 C12 1.526(3) . ?
C11 C13 1.537(2) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.553(3) . ?
C13 C17 1.559(3) . ?
C13 H13 1.0000 . ?
C14 C15 1.558(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.538(2) . ?
C15 C17 1.560(3) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.522(3) . ?
C17 C19 1.538(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 N9 111.40(14) . . ?
C3 C2 C1 112.27(13) . . ?
N9 C2 C1 108.55(14) . . ?
C3 C2 H2 108.2 . . ?
N9 C2 H2 108.2 . . ?
C1 C2 H2 108.2 . . ?
C8 C3 C4 119.63(17) . . ?
C8 C3 C2 120.96(17) . . ?
C4 C3 C2 119.3(2) . . ?
C3 C4 C5 119.5(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 120.25(19) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.2(2) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C3 C8 C7 120.0(2) . . ?
C3 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 N9 C2 115.19(12) . . ?
C10 N9 H9A 108.5 . . ?
C2 N9 H9A 108.5 . . ?
C10 N9 H9B 108.5 . . ?
C2 N9 H9B 108.5 . . ?
H9A N9 H9B 107.5 . . ?
N9 C10 C16 111.01(13) . . ?
N9 C10 C11 110.36(13) . . ?
C16 C10 C11 114.11(14) . . ?
N9 C10 H10 107.0 . . ?
C16 C10 H10 107.0 . . ?
C11 C10 H10 107.0 . . ?
C12 C11 C13 110.23(15) . . ?
C12 C11 C10 111.33(15) . . ?
C13 C11 C10 109.38(14) . . ?
C12 C11 H11 108.6 . . ?
C13 C11 H11 108.6 . . ?
C10 C11 H11 108.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 C14 109.20(15) . . ?
C11 C13 C17 112.52(14) . . ?
C14 C13 C17 87.64(14) . . ?
C11 C13 H13 114.8 . . ?
C14 C13 H13 114.8 . . ?
C17 C13 H13 114.8 . . ?
C13 C14 C15 85.70(13) . . ?
C13 C14 H14A 114.4 . . ?
C15 C14 H14A 114.4 . . ?
C13 C14 H14B 114.4 . . ?
C15 C14 H14B 114.4 . . ?
H14A C14 H14B 111.5 . . ?
C16 C15 C14 109.62(16) . . ?
C16 C15 C17 110.21(14) . . ?
C14 C15 C17 87.47(14) . . ?
C16 C15 H15 115.4 . . ?
C14 C15 H15 115.4 . . ?
C17 C15 H15 115.4 . . ?
C15 C16 C10 110.07(14) . . ?
C15 C16 H16A 109.6 . . ?
C10 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
C10 C16 H16B 109.6 . . ?
H16A C16 H16B 108.2 . . ?
C18 C17 C19 107.52(17) . . ?
C18 C17 C13 119.73(16) . . ?
C19 C17 C13 111.56(16) . . ?
C18 C17 C15 119.25(16) . . ?
C19 C17 C15 112.13(15) . . ?
C13 C17 C15 85.42(14) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
N9 C2 C3 C8 -59.39(19) . . . . ?
C1 C2 C3 C8 62.6(2) . . . . ?
N9 C2 C3 C4 125.03(17) . . . . ?
C1 C2 C3 C4 -112.99(19) . . . . ?
C8 C3 C4 C5 -1.0(3) . . . . ?
C2 C3 C4 C5 174.64(16) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
C5 C6 C7 C8 -1.2(3) . . . . ?
C4 C3 C8 C7 1.0(3) . . . . ?
C2 C3 C8 C7 -174.55(16) . . . . ?
C6 C7 C8 C3 0.1(3) . . . . ?
C3 C2 N9 C10 -53.81(18) . . . . ?
C1 C2 N9 C10 -177.92(14) . . . . ?
C2 N9 C10 C16 -52.99(19) . . . . ?
C2 N9 C10 C11 179.46(13) . . . . ?
N9 C10 C11 C12 -82.36(17) . . . . ?
C16 C10 C11 C12 151.83(16) . . . . ?
N9 C10 C11 C13 155.58(14) . . . . ?
C16 C10 C11 C13 29.8(2) . . . . ?
C12 C11 C13 C14 -89.53(19) . . . . ?
C10 C11 C13 C14 33.19(19) . . . . ?
C12 C11 C13 C17 174.89(16) . . . . ?
C10 C11 C13 C17 -62.39(19) . . . . ?
C11 C13 C14 C15 -85.48(16) . . . . ?
C17 C13 C14 C15 27.58(13) . . . . ?
C13 C14 C15 C16 83.00(16) . . . . ?
C13 C14 C15 C17 -27.57(13) . . . . ?
C14 C15 C16 C10 -29.4(2) . . . . ?
C17 C15 C16 C10 65.3(2) . . . . ?
N9 C10 C16 C15 -157.12(14) . . . . ?
C11 C10 C16 C15 -31.6(2) . . . . ?
C11 C13 C17 C18 -39.0(2) . . . . ?
C14 C13 C17 C18 -148.80(17) . . . . ?
C11 C13 C17 C19 -165.71(16) . . . . ?
C14 C13 C17 C19 84.46(17) . . . . ?
C11 C13 C17 C15 82.29(16) . . . . ?
C14 C13 C17 C15 -27.55(12) . . . . ?
C16 C15 C17 C18 39.2(2) . . . . ?
C14 C15 C17 C18 149.15(17) . . . . ?
C16 C15 C17 C19 166.05(17) . . . . ?
C14 C15 C17 C19 -83.96(18) . . . . ?
C16 C15 C17 C13 -82.52(16) . . . . ?
C14 C15 C17 C13 27.47(12) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_DG181C
_database_code_depnum_ccdc_archive 'CCDC 2110270'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;Institut des Sciences Chimiques de Rennes
France
;
_audit_update_record             
;
2021-09-16 deposited with the CCDC.	2021-11-18 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 26/10/2010                                               #
#------------------------------------------------------------------------------#


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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H30 N, Cl'
_chemical_formula_sum            'C18 H30 Cl N'
_chemical_formula_weight         295.88
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

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

_cell_length_a                   11.4383(9)
_cell_length_b                   10.9604(14)
_cell_length_c                   14.2059(13)
_cell_angle_alpha                90
_cell_angle_beta                 98.636(4)
_cell_angle_gamma                90
_cell_volume                     1760.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2278
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      21.56
_cell_measurement_wavelength     0.71073


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.0524112
_diffrn_orient_matrix_UB_21      -0.0588688
_diffrn_orient_matrix_UB_31      -0.0400066
_diffrn_orient_matrix_UB_12      -0.0623085
_diffrn_orient_matrix_UB_22      0.0650731
_diffrn_orient_matrix_UB_32      -0.0141253
_diffrn_orient_matrix_UB_13      0.0236617
_diffrn_orient_matrix_UB_23      0.0081885
_diffrn_orient_matrix_UB_33      -0.0666516


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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.116
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             648
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.648
_exptl_absorpt_correction_T_max  0.983

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

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

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.33
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_uneti/neti     0.0957
_diffrn_reflns_av_r_equivalents  0.0447
_diffrn_reflns_number            13274
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.096
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_reflns_number_total             7320
_reflns_number_gt                5011
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_max     0.813
_reflns_Friedel_fraction_full    0.853

_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.
;

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

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SIR97 (A. Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0401P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7320
_refine_ls_number_parameters     369
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1121
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
Flack x determined using 1586 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(5)

#------------------------------------------------------------------------------#
#               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 0.0000 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'
Cl Cl 0.1484 0.1585 '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_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 0.86909(8) 0.22079(10) 0.33836(6) 0.0282(3) Uani 1 1 d . . . . .
C1 C 0.5727(4) 0.2949(5) -0.1742(3) 0.0475(14) Uani 1 1 d . . . . .
H1A H 0.531428 0.371889 -0.191549 0.071 Uiso 1 1 calc R U . . .
H1B H 0.515286 0.232716 -0.161949 0.071 Uiso 1 1 calc R U . . .
H1C H 0.613374 0.268067 -0.226573 0.071 Uiso 1 1 calc R U . . .
C2 C 0.6632(4) 0.3137(4) -0.0846(3) 0.0323(11) Uani 1 1 d . . . . .
H2 H 0.619079 0.336838 -0.031538 0.039 Uiso 1 1 calc R U . . .
C3 C 0.7307(3) 0.1946(4) -0.0560(3) 0.0298(11) Uani 1 1 d . . . . .
H3A H 0.672883 0.129364 -0.048603 0.036 Uiso 1 1 calc R U . . .
H3B H 0.774505 0.170073 -0.108019 0.036 Uiso 1 1 calc R U . . .
C4 C 0.8175(3) 0.2054(4) 0.0361(2) 0.0226(9) Uani 1 1 d . . . . .
H4 H 0.864110 0.128007 0.044725 0.027 Uiso 1 1 calc R U . . .
C5 C 0.9051(3) 0.3112(4) 0.0312(3) 0.0250(9) Uani 1 1 d . . . . .
H5 H 0.953255 0.288072 -0.019260 0.030 Uiso 1 1 calc R U . . .
C6 C 0.8414(4) 0.4292(4) -0.0031(3) 0.0304(11) Uani 1 1 d . . . . .
H6A H 0.799485 0.460850 0.047898 0.037 Uiso 1 1 calc R U . . .
H6B H 0.900913 0.490744 -0.014806 0.037 Uiso 1 1 calc R U . . .
C7 C 0.7528(4) 0.4131(5) -0.0937(3) 0.0390(12) Uani 1 1 d . . . . .
H7A H 0.710615 0.491104 -0.109054 0.047 Uiso 1 1 calc R U . . .
H7B H 0.795959 0.392908 -0.147024 0.047 Uiso 1 1 calc R U . . .
C8 C 0.9937(4) 0.3274(4) 0.1229(3) 0.0285(10) Uani 1 1 d . . . . .
H8 H 0.946906 0.344444 0.175497 0.034 Uiso 1 1 calc R U . . .
C9 C 1.0665(3) 0.2133(5) 0.1502(3) 0.0361(11) Uani 1 1 d . . . . .
H9A H 1.115267 0.195177 0.100780 0.054 Uiso 1 1 calc R U . . .
H9B H 1.013465 0.144455 0.156234 0.054 Uiso 1 1 calc R U . . .
H9C H 1.117656 0.226730 0.211043 0.054 Uiso 1 1 calc R U . . .
C10 C 1.0764(4) 0.4363(4) 0.1173(3) 0.0375(12) Uani 1 1 d . . . . .
H10A H 1.134641 0.439746 0.175295 0.056 Uiso 1 1 calc R U . . .
H10B H 1.030050 0.511881 0.111065 0.056 Uiso 1 1 calc R U . . .
H10C H 1.117295 0.426959 0.061830 0.056 Uiso 1 1 calc R U . . .
N11 N 0.7529(2) 0.2201(3) 0.12154(19) 0.0208(7) Uani 1 1 d . . . . .
H11A H 0.710542 0.290517 0.113453 0.025 Uiso 1 1 calc R U . . .
H11B H 0.808519 0.230224 0.173914 0.025 Uiso 1 1 calc R U . . .
C12 C 0.6688(3) 0.1186(4) 0.1439(3) 0.0245(10) Uani 1 1 d . . . . .
H12 H 0.667862 0.122732 0.214135 0.029 Uiso 1 1 calc R U . . .
C13 C 0.5420(3) 0.1450(4) 0.0969(3) 0.0332(11) Uani 1 1 d . . . . .
H13A H 0.488067 0.086667 0.120162 0.050 Uiso 1 1 calc R U . . .
H13B H 0.536718 0.137217 0.027710 0.050 Uiso 1 1 calc R U . . .
H13C H 0.520161 0.228133 0.112866 0.050 Uiso 1 1 calc R U . . .
C14 C 0.7183(3) -0.0057(4) 0.1253(3) 0.0238(10) Uani 1 1 d . . . . .
C15 C 0.6631(4) -0.0853(4) 0.0563(3) 0.0326(11) Uani 1 1 d . . . . .
H15 H 0.592574 -0.061120 0.016584 0.039 Uiso 1 1 calc R U . . .
C16 C 0.7108(4) -0.2002(5) 0.0452(3) 0.0360(12) Uani 1 1 d . . . . .
H16 H 0.672102 -0.254627 -0.001374 0.043 Uiso 1 1 calc R U . . .
C17 C 0.8139(4) -0.2353(4) 0.1016(3) 0.0357(12) Uani 1 1 d . . . . .
H17 H 0.846475 -0.313671 0.093572 0.043 Uiso 1 1 calc R U . . .
C18 C 0.8698(4) -0.1569(4) 0.1697(3) 0.0352(11) Uani 1 1 d . . . . .
H18 H 0.941456 -0.180727 0.208011 0.042 Uiso 1 1 calc R U . . .
C19 C 0.8221(3) -0.0444(4) 0.1820(3) 0.0287(10) Uani 1 1 d . . . . .
H19 H 0.860418 0.008358 0.230065 0.034 Uiso 1 1 calc R U . . .
Cl2 Cl 0.38486(9) -0.02971(10) 0.84499(6) 0.0313(3) Uani 1 1 d . . . . .
C21 C 0.6395(4) -0.1640(7) 0.7135(4) 0.0685(19) Uani 1 1 d . . . . .
H21A H 0.697390 -0.140081 0.672655 0.103 Uiso 1 1 calc R U . . .
H21B H 0.658926 -0.245462 0.739716 0.103 Uiso 1 1 calc R U . . .
H21C H 0.641333 -0.105263 0.765766 0.103 Uiso 1 1 calc R U . . .
C22 C 0.5160(4) -0.1658(5) 0.6551(3) 0.0402(13) Uani 1 1 d . . . . .
H22 H 0.458069 -0.184419 0.699290 0.048 Uiso 1 1 calc R U . . .
C23 C 0.4843(3) -0.0410(5) 0.6103(3) 0.0347(11) Uani 1 1 d . . . . .
H23A H 0.541194 -0.020450 0.566637 0.042 Uiso 1 1 calc R U . . .
H23B H 0.491675 0.021545 0.661087 0.042 Uiso 1 1 calc R U . . .
C24 C 0.3588(3) -0.0376(4) 0.5550(2) 0.0258(9) Uani 1 1 d . . . . .
H24 H 0.348884 0.042012 0.520355 0.031 Uiso 1 1 calc R U . . .
C25 C 0.3374(4) -0.1400(4) 0.4804(3) 0.0289(10) Uani 1 1 d . . . . .
H25 H 0.390836 -0.121761 0.432544 0.035 Uiso 1 1 calc R U . . .
C26 C 0.3770(4) -0.2635(5) 0.5229(3) 0.0382(11) Uani 1 1 d . . . . .
H26A H 0.372888 -0.324243 0.470963 0.046 Uiso 1 1 calc R U . . .
H26B H 0.321508 -0.289660 0.566180 0.046 Uiso 1 1 calc R U . . .
C27 C 0.5024(4) -0.2621(5) 0.5781(3) 0.0437(13) Uani 1 1 d . . . . .
H27A H 0.520886 -0.343187 0.607256 0.052 Uiso 1 1 calc R U . . .
H27B H 0.559353 -0.245935 0.533516 0.052 Uiso 1 1 calc R U . . .
C28 C 0.2112(4) -0.1406(5) 0.4244(3) 0.0364(12) Uani 1 1 d . . . . .
H28 H 0.154912 -0.141525 0.471942 0.044 Uiso 1 1 calc R U . . .
C29 C 0.1859(5) -0.2539(5) 0.3617(3) 0.0580(16) Uani 1 1 d . . . . .
H29A H 0.108843 -0.245116 0.321552 0.087 Uiso 1 1 calc R U . . .
H29B H 0.185126 -0.326322 0.402032 0.087 Uiso 1 1 calc R U . . .
H29C H 0.247647 -0.262858 0.321183 0.087 Uiso 1 1 calc R U . . .
C30 C 0.1853(4) -0.0258(5) 0.3635(3) 0.0511(14) Uani 1 1 d . . . . .
H30A H 0.236058 -0.024607 0.313696 0.077 Uiso 1 1 calc R U . . .
H30B H 0.201075 0.046764 0.403716 0.077 Uiso 1 1 calc R U . . .
H30C H 0.102150 -0.025926 0.333929 0.077 Uiso 1 1 calc R U . . .
N31 N 0.2704(2) -0.0400(3) 0.6260(2) 0.0215(7) Uani 1 1 d . . . . .
H31A H 0.241344 -0.117178 0.627398 0.026 Uiso 1 1 calc R U . . .
H31B H 0.310573 -0.023784 0.684917 0.026 Uiso 1 1 calc R U . . .
C32 C 0.1669(3) 0.0469(4) 0.6076(3) 0.0247(10) Uani 1 1 d . . . . .
H32 H 0.114910 0.019261 0.548475 0.030 Uiso 1 1 calc R U . . .
C33 C 0.0964(4) 0.0373(4) 0.6896(3) 0.0333(11) Uani 1 1 d . . . . .
H33A H 0.146628 0.060450 0.749001 0.050 Uiso 1 1 calc R U . . .
H33B H 0.069063 -0.046847 0.694623 0.050 Uiso 1 1 calc R U . . .
H33C H 0.028081 0.092115 0.678205 0.050 Uiso 1 1 calc R U . . .
C34 C 0.2039(3) 0.1767(4) 0.5920(3) 0.0261(10) Uani 1 1 d . . . . .
C35 C 0.1365(4) 0.2441(5) 0.5203(3) 0.0364(11) Uani 1 1 d . . . . .
H35 H 0.074169 0.205879 0.478992 0.044 Uiso 1 1 calc R U . . .
C36 C 0.1603(4) 0.3667(5) 0.5091(3) 0.0473(14) Uani 1 1 d . . . . .
H36 H 0.113166 0.412465 0.460710 0.057 Uiso 1 1 calc R U . . .
C37 C 0.2519(4) 0.4231(5) 0.5675(3) 0.0413(12) Uani 1 1 d . . . . .
H37 H 0.267272 0.507448 0.559972 0.050 Uiso 1 1 calc R U . . .
C38 C 0.3206(4) 0.3563(5) 0.6368(3) 0.0382(12) Uani 1 1 d . . . . .
H38 H 0.385491 0.393975 0.675597 0.046 Uiso 1 1 calc R U . . .
C39 C 0.2959(4) 0.2337(5) 0.6505(3) 0.0320(11) Uani 1 1 d . . . . .
H39 H 0.342046 0.188947 0.700073 0.038 Uiso 1 1 calc R U . . .



#------------------------------------------------------------------------------#
#                              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
C1 C2 1.530(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.514(6) . ?
C2 C3 1.540(6) . ?
C2 H2 1.0000 . ?
C3 C4 1.524(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N11 1.521(4) . ?
C4 C5 1.541(5) . ?
C4 H4 1.0000 . ?
C5 C6 1.527(6) . ?
C5 C8 1.535(5) . ?
C5 H5 1.0000 . ?
C6 C7 1.524(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.520(6) . ?
C8 C10 1.533(6) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
N11 C12 1.535(5) . ?
N11 H11A 0.9100 . ?
N11 H11B 0.9100 . ?
C12 C14 1.514(6) . ?
C12 C13 1.530(5) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.391(6) . ?
C14 C19 1.397(5) . ?
C15 C16 1.390(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.378(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.377(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.370(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C21 C22 1.528(6) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C27 1.511(7) . ?
C22 C23 1.528(7) . ?
C22 H22 1.0000 . ?
C23 C24 1.530(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 N31 1.531(4) . ?
C24 C25 1.539(6) . ?
C24 H24 1.0000 . ?
C25 C26 1.522(6) . ?
C25 C28 1.540(6) . ?
C25 H25 1.0000 . ?
C26 C27 1.528(6) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.531(7) . ?
C28 C30 1.532(7) . ?
C28 H28 1.0000 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
N31 C32 1.511(5) . ?
N31 H31A 0.9100 . ?
N31 H31B 0.9100 . ?
C32 C34 1.510(6) . ?
C32 C33 1.517(5) . ?
C32 H32 1.0000 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 C39 1.388(6) . ?
C34 C35 1.393(6) . ?
C35 C36 1.385(7) . ?
C35 H35 0.9500 . ?
C36 C37 1.382(7) . ?
C36 H36 0.9500 . ?
C37 C38 1.375(6) . ?
C37 H37 0.9500 . ?
C38 C39 1.393(6) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C1 114.1(4) . . ?
C7 C2 C3 108.3(3) . . ?
C1 C2 C3 110.8(4) . . ?
C7 C2 H2 107.8 . . ?
C1 C2 H2 107.8 . . ?
C3 C2 H2 107.8 . . ?
C4 C3 C2 113.3(4) . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
N11 C4 C3 111.2(3) . . ?
N11 C4 C5 110.7(3) . . ?
C3 C4 C5 111.4(3) . . ?
N11 C4 H4 107.8 . . ?
C3 C4 H4 107.8 . . ?
C5 C4 H4 107.8 . . ?
C6 C5 C8 113.3(3) . . ?
C6 C5 C4 111.6(3) . . ?
C8 C5 C4 113.5(3) . . ?
C6 C5 H5 105.9 . . ?
C8 C5 H5 105.9 . . ?
C4 C5 H5 105.9 . . ?
C7 C6 C5 113.4(4) . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C2 C7 C6 112.6(4) . . ?
C2 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
C2 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C10 109.6(3) . . ?
C9 C8 C5 112.8(4) . . ?
C10 C8 C5 112.3(3) . . ?
C9 C8 H8 107.3 . . ?
C10 C8 H8 107.3 . . ?
C5 C8 H8 107.3 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 N11 C12 118.9(3) . . ?
C4 N11 H11A 107.6 . . ?
C12 N11 H11A 107.6 . . ?
C4 N11 H11B 107.6 . . ?
C12 N11 H11B 107.6 . . ?
H11A N11 H11B 107.0 . . ?
C14 C12 C13 116.7(3) . . ?
C14 C12 N11 110.7(3) . . ?
C13 C12 N11 110.8(3) . . ?
C14 C12 H12 106.0 . . ?
C13 C12 H12 106.0 . . ?
N11 C12 H12 106.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 118.2(4) . . ?
C15 C14 C12 123.1(4) . . ?
C19 C14 C12 118.7(4) . . ?
C16 C15 C14 120.2(4) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 120.2(4) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 120.0(4) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 120.0(4) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C14 121.3(4) . . ?
C18 C19 H19 119.3 . . ?
C14 C19 H19 119.3 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C27 C22 C21 112.9(4) . . ?
C27 C22 C23 109.4(4) . . ?
C21 C22 C23 110.9(4) . . ?
C27 C22 H22 107.8 . . ?
C21 C22 H22 107.8 . . ?
C23 C22 H22 107.8 . . ?
C22 C23 C24 112.4(4) . . ?
C22 C23 H23A 109.1 . . ?
C24 C23 H23A 109.1 . . ?
C22 C23 H23B 109.1 . . ?
C24 C23 H23B 109.1 . . ?
H23A C23 H23B 107.9 . . ?
C23 C24 N31 108.9(3) . . ?
C23 C24 C25 112.1(4) . . ?
N31 C24 C25 112.9(3) . . ?
C23 C24 H24 107.6 . . ?
N31 C24 H24 107.6 . . ?
C25 C24 H24 107.6 . . ?
C26 C25 C24 111.6(3) . . ?
C26 C25 C28 113.7(4) . . ?
C24 C25 C28 113.5(4) . . ?
C26 C25 H25 105.8 . . ?
C24 C25 H25 105.8 . . ?
C28 C25 H25 105.8 . . ?
C25 C26 C27 113.3(4) . . ?
C25 C26 H26A 108.9 . . ?
C27 C26 H26A 108.9 . . ?
C25 C26 H26B 108.9 . . ?
C27 C26 H26B 108.9 . . ?
H26A C26 H26B 107.7 . . ?
C22 C27 C26 111.4(4) . . ?
C22 C27 H27A 109.4 . . ?
C26 C27 H27A 109.4 . . ?
C22 C27 H27B 109.4 . . ?
C26 C27 H27B 109.4 . . ?
H27A C27 H27B 108.0 . . ?
C29 C28 C30 109.5(4) . . ?
C29 C28 C25 112.6(4) . . ?
C30 C28 C25 112.0(4) . . ?
C29 C28 H28 107.5 . . ?
C30 C28 H28 107.5 . . ?
C25 C28 H28 107.5 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C32 N31 C24 116.9(3) . . ?
C32 N31 H31A 108.1 . . ?
C24 N31 H31A 108.1 . . ?
C32 N31 H31B 108.1 . . ?
C24 N31 H31B 108.1 . . ?
H31A N31 H31B 107.3 . . ?
C34 C32 N31 113.0(3) . . ?
C34 C32 C33 111.8(3) . . ?
N31 C32 C33 108.4(3) . . ?
C34 C32 H32 107.8 . . ?
N31 C32 H32 107.8 . . ?
C33 C32 H32 107.8 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C39 C34 C35 119.1(4) . . ?
C39 C34 C32 122.6(4) . . ?
C35 C34 C32 118.1(4) . . ?
C36 C35 C34 120.1(4) . . ?
C36 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C37 C36 C35 120.6(4) . . ?
C37 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
C38 C37 C36 119.5(5) . . ?
C38 C37 H37 120.3 . . ?
C36 C37 H37 120.3 . . ?
C37 C38 C39 120.5(4) . . ?
C37 C38 H38 119.7 . . ?
C39 C38 H38 119.7 . . ?
C34 C39 C38 120.1(4) . . ?
C34 C39 H39 120.0 . . ?
C38 C39 H39 120.0 . . ?

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
C7 C2 C3 C4 57.5(4) . . . . ?
C1 C2 C3 C4 -176.8(3) . . . . ?
C2 C3 C4 N11 69.0(4) . . . . ?
C2 C3 C4 C5 -55.0(4) . . . . ?
N11 C4 C5 C6 -74.6(4) . . . . ?
C3 C4 C5 C6 49.7(4) . . . . ?
N11 C4 C5 C8 54.9(4) . . . . ?
C3 C4 C5 C8 179.2(3) . . . . ?
C8 C5 C6 C7 -179.5(3) . . . . ?
C4 C5 C6 C7 -49.9(4) . . . . ?
C1 C2 C7 C6 -180.0(4) . . . . ?
C3 C2 C7 C6 -56.2(5) . . . . ?
C5 C6 C7 C2 54.5(5) . . . . ?
C6 C5 C8 C9 -173.5(3) . . . . ?
C4 C5 C8 C9 57.8(4) . . . . ?
C6 C5 C8 C10 -49.0(5) . . . . ?
C4 C5 C8 C10 -177.7(3) . . . . ?
C3 C4 N11 C12 60.5(5) . . . . ?
C5 C4 N11 C12 -175.1(3) . . . . ?
C4 N11 C12 C14 38.1(4) . . . . ?
C4 N11 C12 C13 -92.9(4) . . . . ?
C13 C12 C14 C15 11.6(5) . . . . ?
N11 C12 C14 C15 -116.3(4) . . . . ?
C13 C12 C14 C19 -166.2(4) . . . . ?
N11 C12 C14 C19 65.9(4) . . . . ?
C19 C14 C15 C16 0.3(6) . . . . ?
C12 C14 C15 C16 -177.5(4) . . . . ?
C14 C15 C16 C17 -0.9(6) . . . . ?
C15 C16 C17 C18 0.4(7) . . . . ?
C16 C17 C18 C19 0.8(7) . . . . ?
C17 C18 C19 C14 -1.4(6) . . . . ?
C15 C14 C19 C18 0.9(6) . . . . ?
C12 C14 C19 C18 178.8(4) . . . . ?
C27 C22 C23 C24 57.6(5) . . . . ?
C21 C22 C23 C24 -177.2(4) . . . . ?
C22 C23 C24 N31 71.7(5) . . . . ?
C22 C23 C24 C25 -53.8(4) . . . . ?
C23 C24 C25 C26 49.1(4) . . . . ?
N31 C24 C25 C26 -74.2(4) . . . . ?
C23 C24 C25 C28 179.1(3) . . . . ?
N31 C24 C25 C28 55.7(5) . . . . ?
C24 C25 C26 C27 -50.3(5) . . . . ?
C28 C25 C26 C27 179.9(3) . . . . ?
C21 C22 C27 C26 178.5(4) . . . . ?
C23 C22 C27 C26 -57.6(5) . . . . ?
C25 C26 C27 C22 55.4(5) . . . . ?
C26 C25 C28 C29 -42.4(5) . . . . ?
C24 C25 C28 C29 -171.3(4) . . . . ?
C26 C25 C28 C30 -166.3(4) . . . . ?
C24 C25 C28 C30 64.8(5) . . . . ?
C23 C24 N31 C32 136.1(4) . . . . ?
C25 C24 N31 C32 -98.8(4) . . . . ?
C24 N31 C32 C34 -51.0(4) . . . . ?
C24 N31 C32 C33 -175.5(3) . . . . ?
N31 C32 C34 C39 -46.4(5) . . . . ?
C33 C32 C34 C39 76.2(5) . . . . ?
N31 C32 C34 C35 138.7(4) . . . . ?
C33 C32 C34 C35 -98.8(4) . . . . ?
C39 C34 C35 C36 -1.1(6) . . . . ?
C32 C34 C35 C36 174.0(4) . . . . ?
C34 C35 C36 C37 1.1(7) . . . . ?
C35 C36 C37 C38 0.7(7) . . . . ?
C36 C37 C38 C39 -2.3(7) . . . . ?
C35 C34 C39 C38 -0.6(6) . . . . ?
C32 C34 C39 C38 -175.4(4) . . . . ?
C37 C38 C39 C34 2.3(7) . . . . ?

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#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


