# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2018

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

data_shelx_a
_database_code_depnum_ccdc_archive 'CCDC 1815929'
_audit_update_record             
;
2018-01-10 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        3PiNHPl
_chemical_name_common            3PiNHPl
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H24 N2 O2'
_chemical_formula_sum            'C19 H24 N2 O2'
_chemical_formula_weight         312.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.7785(2)
_cell_length_b                   9.8025(3)
_cell_length_c                   25.4462(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.7017(18)
_cell_angle_gamma                90
_cell_volume                     1685.11(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    15416
_cell_measurement_theta_min      3.49
_cell_measurement_theta_max      68.25

_exptl_crystal_description       0.239
_exptl_crystal_colour            block
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.106
_exptl_absorpt_coefficient_mu    0.636
_shelx_estimated_absorpt_T_min   0.863
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID-II IP Area Detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29533
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.486
_diffrn_reflns_theta_max         68.253
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3080
_reflns_number_gt                2610
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'SHELXL-2016/6 (Sheldrick, 2016)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0551P)²+0.1581P] 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         3080
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.1001
_refine_ls_wR_factor_gt          0.0971
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.69755(14) 0.16121(8) 0.44664(3) 0.0344(2) Uani 1 1 d . . . . .
O2 O 0.76592(13) 0.58940(8) 0.37900(3) 0.0346(2) Uani 1 1 d . . . . .
N1 N 0.73303(15) 0.36075(10) 0.40025(3) 0.0268(2) Uani 1 1 d . . . . .
N2 N 0.72801(15) 0.23535(10) 0.56912(4) 0.0261(2) Uani 1 1 d . . . . .
C1 C 0.71508(19) 0.29869(12) 0.34739(4) 0.0296(3) Uani 1 1 d . . . . .
H1 H 0.695410 0.198502 0.352218 0.036 Uiso 1 1 calc R U . . .
C2 C 0.53517(19) 0.35167(14) 0.31375(5) 0.0361(3) Uani 1 1 d . . . . .
H2A H 0.548500 0.451185 0.308416 0.043 Uiso 1 1 calc R U . . .
H2B H 0.414227 0.335504 0.332173 0.043 Uiso 1 1 calc R U . . .
C3 C 0.5163(2) 0.27961(17) 0.26029(5) 0.0486(4) Uani 1 1 d . . . . .
H3A H 0.488763 0.181588 0.265552 0.058 Uiso 1 1 calc R U . . .
H3B H 0.403393 0.318847 0.238157 0.058 Uiso 1 1 calc R U . . .
C4 C 0.7043(2) 0.29438(16) 0.23187(5) 0.0476(4) Uani 1 1 d . . . . .
H4A H 0.690460 0.241648 0.198595 0.057 Uiso 1 1 calc R U . . .
H4B H 0.723507 0.391477 0.222885 0.057 Uiso 1 1 calc R U . . .
C5 C 0.8832(2) 0.24379(15) 0.26583(5) 0.0439(4) Uani 1 1 d . . . . .
H5A H 1.003850 0.259582 0.247248 0.053 Uiso 1 1 calc R U . . .
H5B H 0.870505 0.144374 0.271510 0.053 Uiso 1 1 calc R U . . .
C6 C 0.9042(2) 0.31654(14) 0.31933(5) 0.0358(3) Uani 1 1 d . . . . .
H6A H 1.017990 0.278051 0.341345 0.043 Uiso 1 1 calc R U . . .
H6B H 0.929564 0.414847 0.314050 0.043 Uiso 1 1 calc R U . . .
C7 C 0.72411(17) 0.28307(12) 0.44662(4) 0.0247(3) Uani 1 1 d . . . . .
C8 C 0.74763(16) 0.38146(11) 0.49140(4) 0.0226(3) Uani 1 1 d . . . . .
C9 C 0.75670(16) 0.51165(11) 0.46966(4) 0.0236(3) Uani 1 1 d . . . . .
C10 C 0.75427(17) 0.49894(11) 0.41129(5) 0.0259(3) Uani 1 1 d . . . . .
C11 C 0.75644(17) 0.62960(11) 0.49892(5) 0.0268(3) Uani 1 1 d . . . . .
H11 H 0.760381 0.717246 0.483102 0.032 Uiso 1 1 calc R U . . .
C12 C 0.75005(17) 0.61293(12) 0.55315(5) 0.0277(3) Uani 1 1 d . . . . .
H12 H 0.748992 0.691460 0.575001 0.033 Uiso 1 1 calc R U . . .
C13 C 0.74520(17) 0.48508(12) 0.57600(4) 0.0262(3) Uani 1 1 d . . . . .
H13 H 0.743691 0.478846 0.613217 0.031 Uiso 1 1 calc R U . . .
C14 C 0.74240(16) 0.36317(11) 0.54616(4) 0.0230(3) Uani 1 1 d . . . . .
C15 C 0.88069(18) 0.13388(12) 0.55945(5) 0.0291(3) Uani 1 1 d . . . . .
H15A H 1.001179 0.152025 0.583091 0.035 Uiso 1 1 calc R U . . .
H15B H 0.916019 0.141832 0.522585 0.035 Uiso 1 1 calc R U . . .
C16 C 0.8072(2) -0.00962(12) 0.56906(5) 0.0375(3) Uani 1 1 d . . . . .
H16A H 0.914021 -0.076023 0.563974 0.045 Uiso 1 1 calc R U . . .
H16B H 0.693949 -0.030861 0.543298 0.045 Uiso 1 1 calc R U . . .
C17 C 0.7430(2) -0.02254(13) 0.62497(6) 0.0414(3) Uani 1 1 d . . . . .
H17A H 0.683632 -0.113552 0.629675 0.050 Uiso 1 1 calc R U . . .
H17B H 0.859709 -0.013369 0.650777 0.050 Uiso 1 1 calc R U . . .
C18 C 0.5925(2) 0.08799(13) 0.63471(5) 0.0385(3) Uani 1 1 d . . . . .
H18A H 0.469497 0.071391 0.611855 0.046 Uiso 1 1 calc R U . . .
H18B H 0.559495 0.083512 0.671857 0.046 Uiso 1 1 calc R U . . .
C19 C 0.6710(2) 0.22899(12) 0.62347(4) 0.0318(3) Uani 1 1 d . . . . .
H19A H 0.567888 0.298163 0.628534 0.038 Uiso 1 1 calc R U . . .
H19B H 0.787305 0.249397 0.648346 0.038 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.2081(14) . ?
O2 C10 1.2158(14) . ?
N1 C10 1.3885(15) . ?
N1 C7 1.4097(14) . ?
N1 C1 1.4723(14) . ?
N2 C14 1.3893(14) . ?
N2 C19 1.4672(13) . ?
N2 C15 1.4707(14) . ?
C1 C2 1.5227(18) . ?
C1 C6 1.5277(16) . ?
C1 H1 1.0000 . ?
C2 C3 1.5289(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.523(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.514(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5332(17) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.4914(15) . ?
C8 C9 1.3943(15) . ?
C8 C14 1.4081(15) . ?
C9 C11 1.3752(15) . ?
C9 C10 1.4893(15) . ?
C11 C12 1.3939(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.3830(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.4151(15) . ?
C13 H13 0.9500 . ?
C15 C16 1.5188(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5267(17) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.5224(18) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.5168(17) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 C7 111.62(9) . . ?
C10 N1 C1 125.97(9) . . ?
C7 N1 C1 122.38(10) . . ?
C14 N2 C19 117.89(9) . . ?
C14 N2 C15 117.70(9) . . ?
C19 N2 C15 111.85(9) . . ?
N1 C1 C2 112.03(10) . . ?
N1 C1 C6 111.71(10) . . ?
C2 C1 C6 111.24(10) . . ?
N1 C1 H1 107.2 . . ?
C2 C1 H1 107.2 . . ?
C6 C1 H1 107.2 . . ?
C1 C2 C3 110.33(11) . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C2 111.49(12) . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C5 C4 C3 111.12(11) . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 C6 111.49(11) . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C1 C6 C5 109.95(11) . . ?
C1 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
C1 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
O1 C7 N1 123.44(10) . . ?
O1 C7 C8 130.22(10) . . ?
N1 C7 C8 106.32(10) . . ?
C9 C8 C14 120.97(10) . . ?
C9 C8 C7 107.11(9) . . ?
C14 C8 C7 131.59(10) . . ?
C11 C9 C8 123.56(10) . . ?
C11 C9 C10 127.57(10) . . ?
C8 C9 C10 108.78(9) . . ?
O2 C10 N1 125.89(11) . . ?
O2 C10 C9 128.09(11) . . ?
N1 C10 C9 106.02(9) . . ?
C9 C11 C12 116.03(10) . . ?
C9 C11 H11 122.0 . . ?
C12 C11 H11 122.0 . . ?
C13 C12 C11 121.75(10) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C14 122.65(11) . . ?
C12 C13 H13 118.7 . . ?
C14 C13 H13 118.7 . . ?
N2 C14 C8 122.64(10) . . ?
N2 C14 C13 122.29(10) . . ?
C8 C14 C13 115.03(10) . . ?
N2 C15 C16 110.78(10) . . ?
N2 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C15 C16 C17 110.44(10) . . ?
C15 C16 H16A 109.6 . . ?
C17 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
C17 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
C18 C17 C16 109.80(11) . . ?
C18 C17 H17A 109.7 . . ?
C16 C17 H17A 109.7 . . ?
C18 C17 H17B 109.7 . . ?
C16 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C19 C18 C17 111.56(11) . . ?
C19 C18 H18A 109.3 . . ?
C17 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
C17 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
N2 C19 C18 109.88(10) . . ?
N2 C19 H19A 109.7 . . ?
C18 C19 H19A 109.7 . . ?
N2 C19 H19B 109.7 . . ?
C18 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N1 C1 C2 -60.07(15) . . . . ?
C7 N1 C1 C2 117.92(12) . . . . ?
C10 N1 C1 C6 65.51(15) . . . . ?
C7 N1 C1 C6 -116.50(12) . . . . ?
N1 C1 C2 C3 -177.20(11) . . . . ?
C6 C1 C2 C3 56.96(15) . . . . ?
C1 C2 C3 C4 -55.78(17) . . . . ?
C2 C3 C4 C5 55.38(18) . . . . ?
C3 C4 C5 C6 -55.72(17) . . . . ?
N1 C1 C6 C5 176.91(10) . . . . ?
C2 C1 C6 C5 -57.08(14) . . . . ?
C4 C5 C6 C1 56.37(16) . . . . ?
C10 N1 C7 O1 176.79(11) . . . . ?
C1 N1 C7 O1 -1.46(18) . . . . ?
C10 N1 C7 C8 -1.69(12) . . . . ?
C1 N1 C7 C8 -179.94(10) . . . . ?
O1 C7 C8 C9 -174.73(12) . . . . ?
N1 C7 C8 C9 3.61(12) . . . . ?
O1 C7 C8 C14 -1.4(2) . . . . ?
N1 C7 C8 C14 176.96(11) . . . . ?
C14 C8 C9 C11 -1.60(18) . . . . ?
C7 C8 C9 C11 172.61(11) . . . . ?
C14 C8 C9 C10 -178.31(10) . . . . ?
C7 C8 C9 C10 -4.10(13) . . . . ?
C7 N1 C10 O2 180.00(11) . . . . ?
C1 N1 C10 O2 -1.83(19) . . . . ?
C7 N1 C10 C9 -0.76(12) . . . . ?
C1 N1 C10 C9 177.41(10) . . . . ?
C11 C9 C10 O2 5.8(2) . . . . ?
C8 C9 C10 O2 -177.66(12) . . . . ?
C11 C9 C10 N1 -173.43(11) . . . . ?
C8 C9 C10 N1 3.12(13) . . . . ?
C8 C9 C11 C12 1.13(18) . . . . ?
C10 C9 C11 C12 177.21(11) . . . . ?
C9 C11 C12 C13 0.29(17) . . . . ?
C11 C12 C13 C14 -1.29(19) . . . . ?
C19 N2 C14 C8 -164.04(11) . . . . ?
C15 N2 C14 C8 57.06(15) . . . . ?
C19 N2 C14 C13 13.46(16) . . . . ?
C15 N2 C14 C13 -125.44(12) . . . . ?
C9 C8 C14 N2 178.23(10) . . . . ?
C7 C8 C14 N2 5.64(19) . . . . ?
C9 C8 C14 C13 0.56(16) . . . . ?
C7 C8 C14 C13 -172.03(11) . . . . ?
C12 C13 C14 N2 -176.86(11) . . . . ?
C12 C13 C14 C8 0.82(17) . . . . ?
C14 N2 C15 C16 -159.11(10) . . . . ?
C19 N2 C15 C16 59.65(13) . . . . ?
N2 C15 C16 C17 -56.61(15) . . . . ?
C15 C16 C17 C18 54.00(16) . . . . ?
C16 C17 C18 C19 -54.58(16) . . . . ?
C14 N2 C19 C18 159.76(11) . . . . ?
C15 N2 C19 C18 -59.08(13) . . . . ?
C17 C18 C19 N2 56.73(15) . . . . ?

_refine_diff_density_max         0.190
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.043



####################################################################### 
# 
# 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_irai1
_database_code_depnum_ccdc_archive 'CCDC 1815932'
_audit_update_record             
;
2018-01-10 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        4PyrNHPI
_chemical_name_common            4PyrNHPI
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H22 N2 O2'
_chemical_formula_sum            'C18 H22 N2 O2'
_chemical_formula_weight         298.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   5.1353(2)
_cell_length_b                   10.3387(4)
_cell_length_c                   29.0552(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.523(3)
_cell_angle_gamma                90
_cell_volume                     1541.11(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    17004
_cell_measurement_theta_min      3.047
_cell_measurement_theta_max      68.314

_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.271
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.671
_shelx_estimated_absorpt_T_min   0.839
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0481104
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_process_details   'abscor T.Higashi RIGAKU'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode x-ray'
_diffrn_measurement_device_type  'RIGAKU VM SPIDER'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            17004
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.045
_diffrn_reflns_theta_max         68.220
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2818
_reflns_number_gt                2106
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       RAPID-AUTO
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        RAPID-AUTO
_computing_structure_solution    shelxs
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0464P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2818
_refine_ls_number_parameters     287
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.0906
_refine_ls_wR_factor_gt          0.0862
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_restrained_S_all      0.961
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.8392(3) 0.79583(15) 0.49928(5) 0.0376(4) Uani 1 1 d . . . . .
H1 H 0.576(3) 0.4749(15) 0.1275(5) 0.050(4) Uiso 1 1 d . . . . .
N1 N 0.8771(2) 0.61861(10) 0.36603(3) 0.0308(3) Uani 1 1 d . . . . .
O1 O 0.53271(19) 0.76028(9) 0.35035(3) 0.0453(3) Uani 1 1 d . . . . .
C2 C 1.0742(3) 0.82397(17) 0.47094(5) 0.0409(4) Uani 1 1 d . . . . .
H2 H 0.164(3) 0.7215(13) 0.1789(5) 0.050(5) Uiso 1 1 d . . . . .
N2 N 0.5183(2) 0.62993(10) 0.16916(4) 0.0359(3) Uani 1 1 d . . . . .
O2 O 1.20559(19) 0.46843(9) 0.35687(3) 0.0433(3) Uani 1 1 d . . . . .
C3 C 1.0183(3) 0.78982(14) 0.42044(5) 0.0361(4) Uani 1 1 d . . . . .
H3 H 0.440(3) 0.7249(12) 0.2517(4) 0.035(4) Uiso 1 1 d . . . . .
C4 C 0.9336(3) 0.64872(12) 0.41493(4) 0.0295(3) Uani 1 1 d . . . . .
H4 H 0.888(2) 0.4605(12) 0.1830(5) 0.041(4) Uiso 1 1 d . . . . .
C5 C 0.7041(3) 0.61720(15) 0.44434(5) 0.0352(4) Uani 1 1 d . . . . .
H5 H 1.123(3) 0.4129(14) 0.2522(4) 0.047(4) Uiso 1 1 d . . . . .
C6 C 0.7603(4) 0.65466(15) 0.49472(5) 0.0398(4) Uani 1 1 d . . . . .
H6 H 1.089(2) 0.5921(12) 0.4239(4) 0.030(3) Uiso 1 1 d . . . . .
C7 C 1.0267(3) 0.53253(12) 0.34027(4) 0.0315(3) Uani 1 1 d . . . . .
H7 H 0.541(3) 0.6656(13) 0.4321(4) 0.041(4) Uiso 1 1 d . . . . .
C8 C 0.6873(3) 0.68000(13) 0.33795(4) 0.0320(3) Uani 1 1 d . . . . .
H8 H 0.667(3) 0.5221(14) 0.4408(4) 0.047(4) Uiso 1 1 d . . . . .
C9 C 0.9197(3) 0.53945(12) 0.29251(4) 0.0297(3) Uani 1 1 d . . . . .
H9 H 0.875(3) 0.8485(13) 0.4077(4) 0.044(4) Uiso 1 1 d . . . . .
C10 C 0.9838(3) 0.47583(13) 0.25251(5) 0.0360(4) Uani 1 1 d . . . . .
H10 H 1.173(3) 0.8044(12) 0.4023(4) 0.039(4) Uiso 1 1 d . . . . .
C11 C 0.8466(3) 0.50488(13) 0.21180(5) 0.0359(4) Uani 1 1 d . . . . .
H11 H 1.224(3) 0.7720(13) 0.4833(5) 0.042(4) Uiso 1 1 d . . . . .
C12 C 0.6451(3) 0.59906(12) 0.20965(4) 0.0310(3) Uani 1 1 d . . . . .
H12 H 1.124(3) 0.9188(15) 0.4743(5) 0.058(5) Uiso 1 1 d . . . . .
C13 C 0.5787(3) 0.66082(13) 0.25103(5) 0.0322(3) Uani 1 1 d . . . . .
H13 H 0.689(3) 0.8521(12) 0.4892(4) 0.033(4) Uiso 1 1 d . . . . .
C14 C 0.7175(3) 0.62863(12) 0.29068(4) 0.0296(3) Uani 1 1 d . . . . .
H14 H 0.597(3) 0.6373(14) 0.5126(5) 0.050(4) Uiso 1 1 d . . . . .
C15 C 0.5740(3) 0.57191(16) 0.12497(5) 0.0372(4) Uani 1 1 d . . . . .
H15 H 0.906(3) 0.5999(14) 0.5073(5) 0.049(4) Uiso 1 1 d . . . . .
C16 C 0.3590(3) 0.62415(14) 0.09276(5) 0.0393(4) Uani 1 1 d . . . . .
H16 H 0.876(3) 0.8180(12) 0.5318(5) 0.038(4) Uiso 1 1 d . . . . .
C17 C 0.3097(4) 0.75827(14) 0.11181(5) 0.0411(4) Uani 1 1 d . . . . .
H17 H 0.407(3) 0.6219(13) 0.0600(5) 0.052(4) Uiso 1 1 d . . . . .
C18 C 0.3389(3) 0.74019(14) 0.16380(5) 0.0366(4) Uani 1 1 d . . . . .
H19 H 0.132(3) 0.7950(14) 0.1028(5) 0.048(4) Uiso 1 1 d . . . . .
H20 H 0.452(3) 0.8164(16) 0.1010(5) 0.061(5) Uiso 1 1 d . . . . .
H21 H 0.749(3) 0.5998(14) 0.1146(5) 0.048(4) Uiso 1 1 d . . . . .
H22 H 0.412(3) 0.8188(14) 0.1794(5) 0.044(4) Uiso 1 1 d . . . . .
H18 H 0.201(3) 0.5710(14) 0.0951(5) 0.049(4) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.518(2) . ?
C1 C6 1.519(2) . ?
C1 H13 1.000(13) . ?
C1 H16 0.983(13) . ?
N1 C8 1.3960(15) . ?
N1 C7 1.4118(16) . ?
N1 C4 1.4710(15) . ?
O1 C8 1.2141(15) . ?
C2 C3 1.5243(19) . ?
C2 H11 0.992(14) . ?
C2 H12 1.017(15) . ?
N2 C12 1.3573(15) . ?
N2 C15 1.4569(17) . ?
N2 C18 1.4697(16) . ?
O2 C7 1.2151(15) . ?
C3 C4 1.5286(18) . ?
C3 H9 1.010(14) . ?
C3 H10 0.985(14) . ?
C4 C5 1.5213(19) . ?
C4 H6 1.015(13) . ?
C5 C6 1.5294(19) . ?
C5 H7 1.024(14) . ?
C5 H8 1.006(14) . ?
C6 H14 1.020(15) . ?
C6 H15 0.995(14) . ?
C7 C9 1.4716(17) . ?
C8 C14 1.4868(17) . ?
C9 C10 1.3877(18) . ?
C9 C14 1.3878(17) . ?
C10 C11 1.3830(19) . ?
C10 H5 0.966(15) . ?
C11 C12 1.4202(18) . ?
C11 H4 0.986(13) . ?
C12 C13 1.4162(18) . ?
C13 C14 1.3688(17) . ?
C13 H3 0.974(13) . ?
C15 C16 1.5154(19) . ?
C15 H1 1.006(14) . ?
C15 H21 1.003(15) . ?
C16 C17 1.518(2) . ?
C16 H17 0.994(14) . ?
C16 H18 0.987(15) . ?
C17 C18 1.5232(19) . ?
C17 H19 1.011(14) . ?
C17 H20 1.008(16) . ?
C18 H2 1.034(15) . ?
C18 H22 0.997(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 110.62(13) . . ?
C2 C1 H13 110.5(7) . . ?
C6 C1 H13 109.5(7) . . ?
C2 C1 H16 110.6(8) . . ?
C6 C1 H16 110.3(8) . . ?
H13 C1 H16 105.1(10) . . ?
C8 N1 C7 111.05(10) . . ?
C8 N1 C4 124.84(10) . . ?
C7 N1 C4 123.82(10) . . ?
C1 C2 C3 110.92(12) . . ?
C1 C2 H11 108.7(8) . . ?
C3 C2 H11 109.5(8) . . ?
C1 C2 H12 109.7(9) . . ?
C3 C2 H12 110.6(8) . . ?
H11 C2 H12 107.4(11) . . ?
C12 N2 C15 124.18(12) . . ?
C12 N2 C18 123.28(11) . . ?
C15 N2 C18 111.86(11) . . ?
C2 C3 C4 111.25(12) . . ?
C2 C3 H9 108.5(8) . . ?
C4 C3 H9 109.7(8) . . ?
C2 C3 H10 111.0(8) . . ?
C4 C3 H10 108.8(8) . . ?
H9 C3 H10 107.5(11) . . ?
N1 C4 C5 111.86(11) . . ?
N1 C4 C3 110.25(10) . . ?
C5 C4 C3 111.68(12) . . ?
N1 C4 H6 104.2(7) . . ?
C5 C4 H6 110.7(7) . . ?
C3 C4 H6 107.9(7) . . ?
C4 C5 C6 111.40(12) . . ?
C4 C5 H7 109.9(8) . . ?
C6 C5 H7 109.0(7) . . ?
C4 C5 H8 107.4(8) . . ?
C6 C5 H8 111.8(7) . . ?
H7 C5 H8 107.2(11) . . ?
C1 C6 C5 111.42(12) . . ?
C1 C6 H14 110.2(8) . . ?
C5 C6 H14 108.6(8) . . ?
C1 C6 H15 108.7(8) . . ?
C5 C6 H15 108.4(8) . . ?
H14 C6 H15 109.4(12) . . ?
O2 C7 N1 123.57(12) . . ?
O2 C7 C9 130.19(12) . . ?
N1 C7 C9 106.25(11) . . ?
O1 C8 N1 125.88(12) . . ?
O1 C8 C14 127.93(12) . . ?
N1 C8 C14 106.18(11) . . ?
C10 C9 C14 119.18(12) . . ?
C10 C9 C7 132.38(13) . . ?
C14 C9 C7 108.43(11) . . ?
C11 C10 C9 118.86(14) . . ?
C11 C10 H5 119.2(8) . . ?
C9 C10 H5 121.9(8) . . ?
C10 C11 C12 121.95(13) . . ?
C10 C11 H4 120.2(8) . . ?
C12 C11 H4 117.8(8) . . ?
N2 C12 C13 120.37(12) . . ?
N2 C12 C11 121.33(12) . . ?
C13 C12 C11 118.30(12) . . ?
C14 C13 C12 117.97(13) . . ?
C14 C13 H3 120.2(8) . . ?
C12 C13 H3 121.8(8) . . ?
C13 C14 C9 123.69(12) . . ?
C13 C14 C8 128.23(13) . . ?
C9 C14 C8 108.08(11) . . ?
N2 C15 C16 103.40(12) . . ?
N2 C15 H1 110.4(8) . . ?
C16 C15 H1 114.0(8) . . ?
N2 C15 H21 111.2(8) . . ?
C16 C15 H21 110.4(8) . . ?
H1 C15 H21 107.5(11) . . ?
C15 C16 C17 103.24(12) . . ?
C15 C16 H17 112.4(9) . . ?
C17 C16 H17 115.0(8) . . ?
C15 C16 H18 109.8(8) . . ?
C17 C16 H18 109.4(9) . . ?
H17 C16 H18 107.0(11) . . ?
C16 C17 C18 103.81(12) . . ?
C16 C17 H19 114.3(8) . . ?
C18 C17 H19 110.6(8) . . ?
C16 C17 H20 107.2(9) . . ?
C18 C17 H20 109.8(8) . . ?
H19 C17 H20 110.8(12) . . ?
N2 C18 C17 103.55(12) . . ?
N2 C18 H2 111.2(8) . . ?
C17 C18 H2 113.2(8) . . ?
N2 C18 H22 111.2(8) . . ?
C17 C18 H22 111.8(8) . . ?
H2 C18 H22 106.0(11) . . ?

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 57.44(17) . . . . ?
C1 C2 C3 C4 -56.17(18) . . . . ?
C8 N1 C4 C5 64.69(16) . . . . ?
C7 N1 C4 C5 -122.01(13) . . . . ?
C8 N1 C4 C3 -60.22(16) . . . . ?
C7 N1 C4 C3 113.08(14) . . . . ?
C2 C3 C4 N1 179.17(12) . . . . ?
C2 C3 C4 C5 54.15(16) . . . . ?
N1 C4 C5 C6 -177.38(11) . . . . ?
C3 C4 C5 C6 -53.26(16) . . . . ?
C2 C1 C6 C5 -56.74(18) . . . . ?
C4 C5 C6 C1 54.74(18) . . . . ?
C8 N1 C7 O2 179.35(13) . . . . ?
C4 N1 C7 O2 5.2(2) . . . . ?
C8 N1 C7 C9 -0.79(14) . . . . ?
C4 N1 C7 C9 -174.90(11) . . . . ?
C7 N1 C8 O1 -178.87(14) . . . . ?
C4 N1 C8 O1 -4.8(2) . . . . ?
C7 N1 C8 C14 0.26(15) . . . . ?
C4 N1 C8 C14 174.30(11) . . . . ?
O2 C7 C9 C10 1.0(3) . . . . ?
N1 C7 C9 C10 -178.80(14) . . . . ?
O2 C7 C9 C14 -179.12(14) . . . . ?
N1 C7 C9 C14 1.04(14) . . . . ?
C14 C9 C10 C11 1.0(2) . . . . ?
C7 C9 C10 C11 -179.15(13) . . . . ?
C9 C10 C11 C12 0.9(2) . . . . ?
C15 N2 C12 C13 179.75(13) . . . . ?
C18 N2 C12 C13 9.9(2) . . . . ?
C15 N2 C12 C11 -0.2(2) . . . . ?
C18 N2 C12 C11 -170.00(13) . . . . ?
C10 C11 C12 N2 177.61(13) . . . . ?
C10 C11 C12 C13 -2.3(2) . . . . ?
N2 C12 C13 C14 -178.25(12) . . . . ?
C11 C12 C13 C14 1.7(2) . . . . ?
C12 C13 C14 C9 0.3(2) . . . . ?
C12 C13 C14 C8 179.48(13) . . . . ?
C10 C9 C14 C13 -1.7(2) . . . . ?
C7 C9 C14 C13 178.47(12) . . . . ?
C10 C9 C14 C8 178.97(12) . . . . ?
C7 C9 C14 C8 -0.89(15) . . . . ?
O1 C8 C14 C13 0.2(3) . . . . ?
N1 C8 C14 C13 -178.91(13) . . . . ?
O1 C8 C14 C9 179.52(14) . . . . ?
N1 C8 C14 C9 0.41(15) . . . . ?
C12 N2 C15 C16 172.42(13) . . . . ?
C18 N2 C15 C16 -16.73(17) . . . . ?
N2 C15 C16 C17 33.16(17) . . . . ?
C15 C16 C17 C18 -37.64(17) . . . . ?
C12 N2 C18 C17 164.36(13) . . . . ?
C15 N2 C18 C17 -6.59(16) . . . . ?
C16 C17 C18 N2 27.22(16) . . . . ?

_refine_diff_density_max         0.233
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.043

_shelxl_version_number           2013-3



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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1815931'
_audit_update_record             
;
2018-01-10 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        4PiNHPI
_chemical_name_common            4PiNHPI
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H24 N2 O2'
_chemical_formula_sum            'C19 H24 N2 O2'
_chemical_formula_weight         312.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.26649(14)
_cell_length_b                   10.6373(3)
_cell_length_c                   15.2944(5)
_cell_angle_alpha                72.6185(17)
_cell_angle_beta                 89.9112(17)
_cell_angle_gamma                83.0728(16)
_cell_volume                     811.18(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9616
_cell_measurement_theta_min      3.030
_cell_measurement_theta_max      68.139

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.055
_exptl_absorpt_coefficient_mu    0.660
_shelx_estimated_absorpt_T_min   0.815
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.736
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_process_details   'abscor T.Higashi RIGAKU'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode x-ray'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            9616
_diffrn_reflns_av_unetI/netI     0.0739
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.030
_diffrn_reflns_theta_max         68.139
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             2924
_reflns_number_gt                2075
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       VM-SPIDER
_computing_cell_refinement       VM-SPIDER
_computing_data_reduction        VM-SPIDER
_computing_structure_solution    shelxs
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0800P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2924
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1497
_refine_ls_wR_factor_gt          0.1298
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.968
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 -0.4238(5) 0.6411(2) -0.27691(16) 0.0478(6) Uani 1 1 d . . . . .
H1 H -0.259(4) 0.597(2) -0.3000(13) 0.051(6) Uiso 1 1 d . . . . .
N1 N -0.2179(3) 0.73185(15) -0.13380(11) 0.0377(4) Uani 1 1 d . . . . .
O1 O -0.2045(3) 0.64569(14) 0.23827(9) 0.0452(4) Uani 1 1 d . . . . .
C2 C -0.4540(5) 0.5706(2) -0.17647(16) 0.0468(6) Uani 1 1 d . . . . .
H2 H -0.561(4) 0.637(2) -0.3175(15) 0.059(7) Uiso 1 1 d . . . . .
N2 N 0.1099(3) 0.78473(15) 0.22554(10) 0.0349(4) Uani 1 1 d . . . . .
O2 O 0.4199(3) 0.92199(13) 0.16679(9) 0.0420(4) Uani 1 1 d . . . . .
C3 C -0.2388(4) 0.5900(2) -0.11794(16) 0.0419(5) Uani 1 1 d . . . . .
H3 H -0.457(4) 0.472(2) -0.1641(13) 0.051(6) Uiso 1 1 d . . . . .
C4 C -0.1785(4) 0.8011(2) -0.23009(14) 0.0403(5) Uani 1 1 d . . . . .
H4 H -0.550(4) 0.834(2) -0.2764(14) 0.061(7) Uiso 1 1 d . . . . .
C5 C -0.3940(4) 0.7864(2) -0.29142(17) 0.0463(6) Uani 1 1 d . . . . .
H5 H -0.360(4) 0.835(2) -0.3588(15) 0.054(6) Uiso 1 1 d . . . . .
C6 C -0.0832(4) 0.76410(18) -0.06599(13) 0.0335(5) Uani 1 1 d . . . . .
H6 H -0.175(4) 0.897(2) -0.2364(13) 0.046(6) Uiso 1 1 d . . . . .
C7 C 0.1146(4) 0.84550(19) -0.08691(15) 0.0363(5) Uani 1 1 d . . . . .
H7 H -0.077(4) 0.543(2) -0.1346(15) 0.062(7) Uiso 1 1 d . . . . .
C8 C -0.1514(4) 0.71607(18) 0.02638(14) 0.0349(5) Uani 1 1 d . . . . .
H8 H -0.266(4) 0.545(2) -0.0503(14) 0.050(6) Uiso 1 1 d . . . . .
C9 C 0.2409(4) 0.8807(2) -0.01958(14) 0.0363(5) Uani 1 1 d . . . . .
H9 H -0.298(3) 0.6618(18) 0.0434(12) 0.033(5) Uiso 1 1 d . . . . .
C10 C -0.0240(3) 0.75149(18) 0.09159(13) 0.0331(5) Uani 1 1 d . . . . .
H10 H 0.166(4) 0.8760(19) -0.1496(13) 0.042(6) Uiso 1 1 d . . . . .
C11 C 0.1706(3) 0.83252(17) 0.07028(13) 0.0320(5) Uani 1 1 d . . . . .
H11 H 0.373(4) 0.938(2) -0.0386(13) 0.051(6) Uiso 1 1 d . . . . .
C12 C -0.0607(4) 0.71742(19) 0.19238(13) 0.0352(5) Uani 1 1 d . . . . .
H12 H 0.098(4) 0.589(2) 0.3893(14) 0.056(7) Uiso 1 1 d . . . . .
C13 C 0.2574(4) 0.85540(19) 0.15496(14) 0.0335(5) Uani 1 1 d . . . . .
H13 H 0.316(4) 0.575(2) 0.5271(15) 0.053(6) Uiso 1 1 d . . . . .
C14 C 0.1335(4) 0.7884(2) 0.32024(13) 0.0353(5) Uani 1 1 d . . . . .
H14 H 0.267(4) 0.846(2) 0.3169(13) 0.047(6) Uiso 1 1 d . . . . .
C15 C -0.1165(4) 0.8493(2) 0.35069(15) 0.0408(5) Uani 1 1 d . . . . .
H15 H -0.170(4) 0.934(2) 0.3057(14) 0.052(6) Uiso 1 1 d . . . . .
C16 C -0.0789(5) 0.8621(2) 0.44592(16) 0.0498(6) Uani 1 1 d . . . . .
H16 H -0.260(4) 0.789(2) 0.3535(12) 0.043(5) Uiso 1 1 d . . . . .
C17 C 0.0159(4) 0.7281(3) 0.51495(16) 0.0523(6) Uani 1 1 d . . . . .
H17 H -0.248(4) 0.901(2) 0.4666(14) 0.060(6) Uiso 1 1 d . . . . .
C18 C 0.2608(5) 0.6645(3) 0.48307(16) 0.0508(6) Uani 1 1 d . . . . .
H18 H 0.041(4) 0.929(2) 0.4413(14) 0.054(6) Uiso 1 1 d . . . . .
C19 C 0.2264(5) 0.6527(2) 0.38741(15) 0.0444(6) Uani 1 1 d . . . . .
H21 H 0.050(4) 0.742(2) 0.5784(14) 0.050(6) Uiso 1 1 d . . . . .
H22 H -0.002(4) 0.764(2) -0.2541(14) 0.052(6) Uiso 1 1 d . . . . .
H23 H 0.391(4) 0.613(2) 0.3683(14) 0.062(7) Uiso 1 1 d . . . . .
H24 H 0.405(4) 0.720(2) 0.4855(14) 0.063(7) Uiso 1 1 d . . . . .
H20 H -0.617(4) 0.607(2) -0.1565(14) 0.054(6) Uiso 1 1 d . . . . .
H19 H -0.122(4) 0.666(2) 0.5251(14) 0.059(7) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.512(3) . ?
C1 C5 1.522(3) . ?
C1 H1 1.05(2) . ?
C1 H2 0.97(2) . ?
N1 C6 1.404(2) . ?
N1 C4 1.464(2) . ?
N1 C3 1.472(2) . ?
O1 C12 1.211(2) . ?
C2 C3 1.516(3) . ?
C2 H3 1.01(2) . ?
C2 H20 0.98(2) . ?
N2 C12 1.397(2) . ?
N2 C13 1.410(2) . ?
N2 C14 1.466(2) . ?
O2 C13 1.221(2) . ?
C3 H7 1.01(2) . ?
C3 H8 1.02(2) . ?
C4 C5 1.525(3) . ?
C4 H6 0.99(2) . ?
C4 H22 1.07(2) . ?
C5 H4 0.98(2) . ?
C5 H5 1.03(2) . ?
C6 C7 1.410(3) . ?
C6 C8 1.413(3) . ?
C7 C9 1.391(3) . ?
C7 H10 0.964(19) . ?
C8 C10 1.369(2) . ?
C8 H9 1.007(18) . ?
C9 C11 1.383(3) . ?
C9 H11 0.97(2) . ?
C10 C11 1.394(2) . ?
C10 C12 1.492(3) . ?
C11 C13 1.471(2) . ?
C14 C19 1.524(3) . ?
C14 C15 1.531(3) . ?
C14 H14 0.98(2) . ?
C15 C16 1.518(3) . ?
C15 H15 0.97(2) . ?
C15 H16 1.04(2) . ?
C16 C17 1.525(3) . ?
C16 H17 1.03(2) . ?
C16 H18 1.00(2) . ?
C17 C18 1.531(3) . ?
C17 H21 1.04(2) . ?
C17 H19 1.02(2) . ?
C18 C19 1.518(3) . ?
C18 H13 1.00(2) . ?
C18 H24 1.03(2) . ?
C19 H12 1.01(2) . ?
C19 H23 1.00(2) . ?

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 C5 110.58(19) . . ?
C2 C1 H1 109.6(11) . . ?
C5 C1 H1 107.9(11) . . ?
C2 C1 H2 115.1(13) . . ?
C5 C1 H2 108.5(13) . . ?
H1 C1 H2 104.8(17) . . ?
C6 N1 C4 118.49(16) . . ?
C6 N1 C3 116.44(15) . . ?
C4 N1 C3 112.41(16) . . ?
C1 C2 C3 111.25(19) . . ?
C1 C2 H3 112.2(11) . . ?
C3 C2 H3 108.1(12) . . ?
C1 C2 H20 109.4(13) . . ?
C3 C2 H20 108.3(12) . . ?
H3 C2 H20 107.4(18) . . ?
C12 N2 C13 111.43(16) . . ?
C12 N2 C14 126.09(16) . . ?
C13 N2 C14 122.45(15) . . ?
N1 C3 C2 111.46(18) . . ?
N1 C3 H7 110.7(13) . . ?
C2 C3 H7 106.8(12) . . ?
N1 C3 H8 110.3(11) . . ?
C2 C3 H8 110.3(11) . . ?
H7 C3 H8 107.2(17) . . ?
N1 C4 C5 110.76(18) . . ?
N1 C4 H6 108.1(11) . . ?
C5 C4 H6 109.6(12) . . ?
N1 C4 H22 112.7(12) . . ?
C5 C4 H22 107.2(10) . . ?
H6 C4 H22 108.5(16) . . ?
C1 C5 C4 111.44(19) . . ?
C1 C5 H4 111.2(13) . . ?
C4 C5 H4 106.7(12) . . ?
C1 C5 H5 112.3(11) . . ?
C4 C5 H5 108.8(11) . . ?
H4 C5 H5 106.1(18) . . ?
N1 C6 C7 122.32(18) . . ?
N1 C6 C8 119.06(17) . . ?
C7 C6 C8 118.60(18) . . ?
C9 C7 C6 121.9(2) . . ?
C9 C7 H10 119.3(11) . . ?
C6 C7 H10 118.8(11) . . ?
C10 C8 C6 118.56(18) . . ?
C10 C8 H9 120.6(10) . . ?
C6 C8 H9 120.8(10) . . ?
C11 C9 C7 118.42(19) . . ?
C11 C9 H11 123.8(12) . . ?
C7 C9 H11 117.8(12) . . ?
C8 C10 C11 122.49(18) . . ?
C8 C10 C12 129.51(18) . . ?
C11 C10 C12 108.00(17) . . ?
C9 C11 C10 120.04(18) . . ?
C9 C11 C13 131.54(18) . . ?
C10 C11 C13 108.36(16) . . ?
O1 C12 N2 125.58(18) . . ?
O1 C12 C10 128.55(18) . . ?
N2 C12 C10 105.86(16) . . ?
O2 C13 N2 123.78(18) . . ?
O2 C13 C11 129.89(18) . . ?
N2 C13 C11 106.31(15) . . ?
N2 C14 C19 112.69(16) . . ?
N2 C14 C15 111.52(16) . . ?
C19 C14 C15 111.05(18) . . ?
N2 C14 H14 102.6(11) . . ?
C19 C14 H14 108.2(12) . . ?
C15 C14 H14 110.3(12) . . ?
C16 C15 C14 110.09(18) . . ?
C16 C15 H15 112.2(12) . . ?
C14 C15 H15 108.2(13) . . ?
C16 C15 H16 107.7(10) . . ?
C14 C15 H16 110.4(11) . . ?
H15 C15 H16 108.2(16) . . ?
C15 C16 C17 111.30(19) . . ?
C15 C16 H17 109.7(12) . . ?
C17 C16 H17 109.5(13) . . ?
C15 C16 H18 107.6(12) . . ?
C17 C16 H18 112.7(13) . . ?
H17 C16 H18 105.9(17) . . ?
C16 C17 C18 110.7(2) . . ?
C16 C17 H21 109.0(11) . . ?
C18 C17 H21 110.0(11) . . ?
C16 C17 H19 110.6(13) . . ?
C18 C17 H19 110.5(12) . . ?
H21 C17 H19 105.9(15) . . ?
C19 C18 C17 112.03(19) . . ?
C19 C18 H13 109.8(12) . . ?
C17 C18 H13 110.0(12) . . ?
C19 C18 H24 110.8(12) . . ?
C17 C18 H24 108.5(13) . . ?
H13 C18 H24 105.5(18) . . ?
C18 C19 C14 110.10(19) . . ?
C18 C19 H12 108.5(12) . . ?
C14 C19 H12 110.2(13) . . ?
C18 C19 H23 109.8(12) . . ?
C14 C19 H23 111.5(13) . . ?
H12 C19 H23 106.5(18) . . ?

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
C5 C1 C2 C3 -53.2(3) . . . . ?
C6 N1 C3 C2 161.31(18) . . . . ?
C4 N1 C3 C2 -57.3(2) . . . . ?
C1 C2 C3 N1 55.0(3) . . . . ?
C6 N1 C4 C5 -162.44(16) . . . . ?
C3 N1 C4 C5 57.0(2) . . . . ?
C2 C1 C5 C4 53.4(3) . . . . ?
N1 C4 C5 C1 -55.1(2) . . . . ?
C4 N1 C6 C7 -9.5(3) . . . . ?
C3 N1 C6 C7 129.5(2) . . . . ?
C4 N1 C6 C8 168.97(18) . . . . ?
C3 N1 C6 C8 -52.1(2) . . . . ?
N1 C6 C7 C9 177.71(16) . . . . ?
C8 C6 C7 C9 -0.8(3) . . . . ?
N1 C6 C8 C10 -178.03(15) . . . . ?
C7 C6 C8 C10 0.5(3) . . . . ?
C6 C7 C9 C11 0.8(3) . . . . ?
C6 C8 C10 C11 -0.2(3) . . . . ?
C6 C8 C10 C12 178.69(17) . . . . ?
C7 C9 C11 C10 -0.5(3) . . . . ?
C7 C9 C11 C13 -177.07(17) . . . . ?
C8 C10 C11 C9 0.2(3) . . . . ?
C12 C10 C11 C9 -178.91(16) . . . . ?
C8 C10 C11 C13 177.55(15) . . . . ?
C12 C10 C11 C13 -1.59(19) . . . . ?
C13 N2 C12 O1 177.52(19) . . . . ?
C14 N2 C12 O1 -4.5(3) . . . . ?
C13 N2 C12 C10 -1.81(19) . . . . ?
C14 N2 C12 C10 176.13(15) . . . . ?
C8 C10 C12 O1 3.7(3) . . . . ?
C11 C10 C12 O1 -177.2(2) . . . . ?
C8 C10 C12 N2 -176.96(17) . . . . ?
C11 C10 C12 N2 2.09(19) . . . . ?
C12 N2 C13 O2 180.00(17) . . . . ?
C14 N2 C13 O2 2.0(3) . . . . ?
C12 N2 C13 C11 0.9(2) . . . . ?
C14 N2 C13 C11 -177.16(15) . . . . ?
C9 C11 C13 O2 -1.6(3) . . . . ?
C10 C11 C13 O2 -178.55(19) . . . . ?
C9 C11 C13 N2 177.41(19) . . . . ?
C10 C11 C13 N2 0.51(19) . . . . ?
C12 N2 C14 C19 65.1(2) . . . . ?
C13 N2 C14 C19 -117.1(2) . . . . ?
C12 N2 C14 C15 -60.6(2) . . . . ?
C13 N2 C14 C15 117.2(2) . . . . ?
N2 C14 C15 C16 -175.28(17) . . . . ?
C19 C14 C15 C16 58.1(2) . . . . ?
C14 C15 C16 C17 -57.1(3) . . . . ?
C15 C16 C17 C18 55.3(3) . . . . ?
C16 C17 C18 C19 -54.8(3) . . . . ?
C17 C18 C19 C14 55.6(3) . . . . ?
N2 C14 C19 C18 176.88(17) . . . . ?
C15 C14 C19 C18 -57.2(2) . . . . ?

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.051



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

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1815930'
_audit_update_record             
;
2018-01-10 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        3PryNHPI
_chemical_name_common            3PryNHPI
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H22 N2 O2'
_chemical_formula_sum            'C18 H22 N2 O2'
_chemical_formula_weight         298.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   10.7455(9)
_cell_length_b                   26.6113(17)
_cell_length_c                   10.8489(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.080(4)
_cell_angle_gamma                90
_cell_volume                     3063.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    34611
_cell_measurement_theta_min      3.322
_cell_measurement_theta_max      68.247

_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.338
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.098
_exptl_absorpt_coefficient_mu    0.675
_shelx_estimated_absorpt_T_min   0.804
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.664
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_process_details   'abscor T.Higashi RIGAKU'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode x-ray'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            34608
_diffrn_reflns_av_unetI/netI     0.1208
_diffrn_reflns_av_R_equivalents  0.1072
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.166
_diffrn_reflns_theta_max         68.247
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5591
_reflns_number_gt                2760
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       VM-SPIDER
_computing_cell_refinement       VM-SPIDER
_computing_data_reduction        VM-SPIDER
_computing_structure_solution    shelxs
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0374P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5591
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1187
_refine_ls_wR_factor_gt          0.0944
_refine_ls_goodness_of_fit_ref   0.833
_refine_ls_restrained_S_all      0.833
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.2287(2) 0.61601(8) 1.0624(2) 0.0409(7) Uani 1 1 d . . . . .
H1A H 0.2503 0.6247 1.1520 0.049 Uiso 1 1 calc R U . . .
H1B H 0.1450 0.6302 1.0293 0.049 Uiso 1 1 calc R U . . .
N1 N 0.23043(19) 0.56109(7) 1.04374(17) 0.0361(5) Uani 1 1 d . . . . .
O1 O 0.31705(16) 0.44168(6) 0.97689(16) 0.0482(5) Uani 1 1 d . . . . .
C2 C 0.3283(3) 0.63504(9) 0.9896(2) 0.0516(8) Uani 1 1 d . . . . .
H2A H 0.3088 0.6695 0.9579 0.062 Uiso 1 1 calc R U . . .
H2B H 0.4129 0.6348 1.0414 0.062 Uiso 1 1 calc R U . . .
O2 O 0.02881(16) 0.35957(6) 1.16857(16) 0.0504(5) Uani 1 1 d . . . . .
N2 N 0.17517(18) 0.39052(6) 1.05279(17) 0.0349(5) Uani 1 1 d . . . . .
C3 C 0.3207(3) 0.59769(9) 0.8838(2) 0.0513(8) Uani 1 1 d . . . . .
H3A H 0.2485 0.6052 0.8177 0.062 Uiso 1 1 calc R U . . .
H3B H 0.3992 0.5978 0.8467 0.062 Uiso 1 1 calc R U . . .
N3 N 0.30891(19) 0.44821(7) 0.43502(18) 0.0375(5) Uani 1 1 d . . . . .
O3 O 0.20349(18) 0.55095(6) 0.57673(17) 0.0585(6) Uani 1 1 d . . . . .
C4 C 0.3030(2) 0.54794(8) 0.9453(2) 0.0371(6) Uani 1 1 d . . . . .
H4A H 0.2560 0.5240 0.8853 0.045 Uiso 1 1 calc R U . . .
H4B H 0.3851 0.5329 0.9807 0.045 Uiso 1 1 calc R U . . .
N4 N 0.28566(18) 0.61871(6) 0.48821(17) 0.0342(5) Uani 1 1 d . . . . .
O4 O 0.39872(16) 0.66916(6) 0.37061(16) 0.0528(5) Uani 1 1 d . . . . .
C5 C 0.1603(2) 0.52916(8) 1.1021(2) 0.0326(6) Uani 1 1 d . . . . .
C6 C 0.0794(2) 0.55048(9) 1.1817(2) 0.0396(6) Uani 1 1 d . . . . .
H6 H 0.0797 0.5859 1.1923 0.048 Uiso 1 1 calc R U . . .
C7 C 0.0021(2) 0.52246(10) 1.2429(2) 0.0440(7) Uani 1 1 d . . . . .
H7 H -0.0493 0.5390 1.2941 0.053 Uiso 1 1 calc R U . . .
C8 C -0.0036(2) 0.47020(9) 1.2323(2) 0.0404(7) Uani 1 1 d . . . . .
H8 H -0.0574 0.4505 1.2746 0.048 Uiso 1 1 calc R U . . .
C9 C 0.0736(2) 0.44924(9) 1.1569(2) 0.0340(6) Uani 1 1 d . . . . .
C10 C 0.1558(2) 0.47606(8) 1.0934(2) 0.0299(6) Uani 1 1 d . . . . .
C11 C 0.2266(2) 0.43789(9) 1.0318(2) 0.0354(6) Uani 1 1 d . . . . .
C13 C 0.0841(2) 0.39495(9) 1.1312(2) 0.0371(6) Uani 1 1 d . . . . .
C14 C 0.3473(2) 0.32767(8) 1.0655(2) 0.0452(7) Uani 1 1 d . . . . .
H14A H 0.3525 0.3265 1.1574 0.054 Uiso 1 1 calc R U . . .
H14B H 0.4072 0.3535 1.0453 0.054 Uiso 1 1 calc R U . . .
C15 C 0.1985(3) 0.34075(9) 0.8640(2) 0.0467(7) Uani 1 1 d . . . . .
H15A H 0.1098 0.3482 0.8286 0.056 Uiso 1 1 calc R U . . .
H15B H 0.2522 0.3670 0.8345 0.056 Uiso 1 1 calc R U . . .
C16 C 0.3846(3) 0.27658(9) 1.0186(3) 0.0565(8) Uani 1 1 d . . . . .
H16A H 0.3315 0.2501 1.0480 0.068 Uiso 1 1 calc R U . . .
H16B H 0.4735 0.2694 1.0538 0.068 Uiso 1 1 calc R U . . .
C17 C 0.2348(3) 0.28952(9) 0.8177(2) 0.0543(8) Uani 1 1 d . . . . .
H17A H 0.2287 0.2903 0.7257 0.065 Uiso 1 1 calc R U . . .
H17B H 0.1753 0.2638 0.8391 0.065 Uiso 1 1 calc R U . . .
C18 C 0.3687(3) 0.27535(9) 0.8762(3) 0.0550(8) Uani 1 1 d . . . . .
H18A H 0.4290 0.2991 0.8473 0.066 Uiso 1 1 calc R U . . .
H18B H 0.3883 0.2412 0.8484 0.066 Uiso 1 1 calc R U . . .
C19 C 0.3383(2) 0.39694(8) 0.3989(2) 0.0470(7) Uani 1 1 d . . . . .
H19A H 0.4304 0.3908 0.4150 0.056 Uiso 1 1 calc R U . . .
H19B H 0.3068 0.3910 0.3093 0.056 Uiso 1 1 calc R U . . .
C20 C 0.2708(3) 0.36352(9) 0.4804(3) 0.0589(8) Uani 1 1 d . . . . .
H20A H 0.2428 0.3318 0.4370 0.071 Uiso 1 1 calc R U . . .
H20B H 0.3259 0.3555 0.5600 0.071 Uiso 1 1 calc R U . . .
C21 C 0.1604(3) 0.39453(9) 0.5028(3) 0.0562(8) Uani 1 1 d . . . . .
H21A H 0.1305 0.3840 0.5806 0.067 Uiso 1 1 calc R U . . .
H21B H 0.0901 0.3913 0.4323 0.067 Uiso 1 1 calc R U . . .
C22 C 0.2093(2) 0.44809(8) 0.5135(2) 0.0393(6) Uani 1 1 d . . . . .
H22A H 0.1418 0.4723 0.4820 0.047 Uiso 1 1 calc R U . . .
H22B H 0.2438 0.4565 0.6011 0.047 Uiso 1 1 calc R U . . .
C23 C 0.3617(2) 0.48940(8) 0.3897(2) 0.0327(6) Uani 1 1 d . . . . .
C24 C 0.4468(2) 0.48145(10) 0.3020(2) 0.0431(7) Uani 1 1 d . . . . .
H24 H 0.4632 0.4479 0.2791 0.052 Uiso 1 1 calc R U . . .
C25 C 0.5055(2) 0.51977(10) 0.2496(2) 0.0475(7) Uani 1 1 d . . . . .
H25 H 0.5613 0.5120 0.1925 0.057 Uiso 1 1 calc R U . . .
C26 C 0.4859(2) 0.56946(10) 0.2775(2) 0.0452(7) Uani 1 1 d . . . . .
H26 H 0.5266 0.5961 0.2415 0.054 Uiso 1 1 calc R U . . .
C27 C 0.4040(2) 0.57806(8) 0.3603(2) 0.0346(6) Uani 1 1 d . . . . .
C28 C 0.3430(2) 0.54022(8) 0.4182(2) 0.0298(6) Uani 1 1 d . . . . .
C29 C 0.2685(2) 0.56652(8) 0.5029(2) 0.0346(6) Uani 1 1 d . . . . .
C30 C 0.3673(2) 0.62794(9) 0.4027(2) 0.0375(6) Uani 1 1 d . . . . .
C31 C 0.2178(2) 0.65653(8) 0.5492(2) 0.0365(6) Uani 1 1 d . . . . .
H31 H 0.1695 0.6382 0.6068 0.044 Uiso 1 1 calc R U . . .
C32 C 0.3048(2) 0.69303(9) 0.6287(2) 0.0491(7) Uani 1 1 d . . . . .
H32A H 0.3533 0.7126 0.5749 0.059 Uiso 1 1 calc R U . . .
H32B H 0.3653 0.6742 0.6899 0.059 Uiso 1 1 calc R U . . .
C33 C 0.1217(2) 0.68441(9) 0.4550(2) 0.0473(7) Uani 1 1 d . . . . .
H33A H 0.0651 0.6599 0.4055 0.057 Uiso 1 1 calc R U . . .
H33B H 0.1659 0.7038 0.3971 0.057 Uiso 1 1 calc R U . . .
C34 C 0.0442(3) 0.72006(10) 0.5232(3) 0.0598(8) Uani 1 1 d . . . . .
H34A H -0.0151 0.7392 0.4614 0.072 Uiso 1 1 calc R U . . .
H34B H -0.0059 0.7003 0.5752 0.072 Uiso 1 1 calc R U . . .
C35 C 0.2277(3) 0.72864(10) 0.6973(3) 0.0630(9) Uani 1 1 d . . . . .
H35A H 0.1853 0.7093 0.7565 0.076 Uiso 1 1 calc R U . . .
H35B H 0.2846 0.7533 0.7457 0.076 Uiso 1 1 calc R U . . .
C36 C 0.1294(3) 0.75629(9) 0.6053(3) 0.0665(10) Uani 1 1 d . . . . .
H36A H 0.0776 0.7777 0.6520 0.080 Uiso 1 1 calc R U . . .
H36B H 0.1724 0.7785 0.5521 0.080 Uiso 1 1 calc R U . . .
C12 C 0.2142(2) 0.34215(8) 1.0065(2) 0.0380(6) Uani 1 1 d . . . . .
H12 H 0.1564 0.3161 1.0322 0.046 Uiso 1 1 calc R U . . .


_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 N1 1.476(3) . ?
C1 C2 1.514(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N1 C5 1.357(3) . ?
N1 C4 1.460(3) . ?
O1 C11 1.221(2) . ?
C2 C3 1.511(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
O2 C13 1.216(3) . ?
N2 C13 1.400(3) . ?
N2 C11 1.409(3) . ?
N2 C12 1.467(3) . ?
C3 C4 1.509(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
N3 C23 1.361(3) . ?
N3 C19 1.468(3) . ?
N3 C22 1.469(3) . ?
O3 C29 1.215(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
N4 C30 1.396(3) . ?
N4 C29 1.413(3) . ?
N4 C31 1.461(3) . ?
O4 C30 1.214(2) . ?
C5 C10 1.417(3) . ?
C5 C6 1.435(3) . ?
C6 C7 1.364(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.396(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.373(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.399(3) . ?
C9 C13 1.479(3) . ?
C10 C11 1.489(3) . ?
C14 C12 1.521(3) . ?
C14 C16 1.527(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C17 1.525(3) . ?
C15 C12 1.529(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C18 1.529(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.526(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.518(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.496(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.517(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C28 1.408(3) . ?
C23 C24 1.436(3) . ?
C24 C25 1.369(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.380(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.372(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.403(3) . ?
C27 C30 1.478(3) . ?
C28 C29 1.486(3) . ?
C31 C32 1.518(3) . ?
C31 C33 1.526(3) . ?
C31 H31 1.0000 . ?
C32 C35 1.527(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.528(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C36 1.518(4) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.523(4) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C12 H12 1.0000 . ?

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
N1 C1 C2 103.56(19) . . ?
N1 C1 H1A 111.0 . . ?
C2 C1 H1A 111.0 . . ?
N1 C1 H1B 111.0 . . ?
C2 C1 H1B 111.0 . . ?
H1A C1 H1B 109.0 . . ?
C5 N1 C4 126.22(19) . . ?
C5 N1 C1 122.4(2) . . ?
C4 N1 C1 110.93(18) . . ?
C3 C2 C1 102.6(2) . . ?
C3 C2 H2A 111.2 . . ?
C1 C2 H2A 111.2 . . ?
C3 C2 H2B 111.2 . . ?
C1 C2 H2B 111.2 . . ?
H2A C2 H2B 109.2 . . ?
C13 N2 C11 110.7(2) . . ?
C13 N2 C12 123.19(19) . . ?
C11 N2 C12 126.1(2) . . ?
C4 C3 C2 103.7(2) . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
C2 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C23 N3 C19 122.2(2) . . ?
C23 N3 C22 126.45(18) . . ?
C19 N3 C22 111.11(19) . . ?
N1 C4 C3 103.47(18) . . ?
N1 C4 H4A 111.1 . . ?
C3 C4 H4A 111.1 . . ?
N1 C4 H4B 111.1 . . ?
C3 C4 H4B 111.1 . . ?
H4A C4 H4B 109.0 . . ?
C30 N4 C29 110.8(2) . . ?
C30 N4 C31 126.22(19) . . ?
C29 N4 C31 122.8(2) . . ?
N1 C5 C10 127.5(2) . . ?
N1 C5 C6 117.8(2) . . ?
C10 C5 C6 114.6(2) . . ?
C7 C6 C5 123.4(2) . . ?
C7 C6 H6 118.3 . . ?
C5 C6 H6 118.3 . . ?
C6 C7 C8 121.8(2) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C9 C8 C7 115.5(2) . . ?
C9 C8 H8 122.2 . . ?
C7 C8 H8 122.2 . . ?
C8 C9 C10 125.1(2) . . ?
C8 C9 C13 125.5(2) . . ?
C10 C9 C13 109.4(2) . . ?
C9 C10 C5 119.6(2) . . ?
C9 C10 C11 106.3(2) . . ?
C5 C10 C11 134.1(2) . . ?
O1 C11 N2 121.0(2) . . ?
O1 C11 C10 131.7(2) . . ?
N2 C11 C10 107.2(2) . . ?
O2 C13 N2 124.2(2) . . ?
O2 C13 C9 129.6(2) . . ?
N2 C13 C9 106.2(2) . . ?
C12 C14 C16 111.4(2) . . ?
C12 C14 H14A 109.4 . . ?
C16 C14 H14A 109.4 . . ?
C12 C14 H14B 109.4 . . ?
C16 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C17 C15 C12 111.2(2) . . ?
C17 C15 H15A 109.4 . . ?
C12 C15 H15A 109.4 . . ?
C17 C15 H15B 109.4 . . ?
C12 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C14 C16 C18 111.3(2) . . ?
C14 C16 H16A 109.4 . . ?
C18 C16 H16A 109.4 . . ?
C14 C16 H16B 109.4 . . ?
C18 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C15 C17 C18 110.9(2) . . ?
C15 C17 H17A 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 108.0 . . ?
C17 C18 C16 111.3(2) . . ?
C17 C18 H18A 109.4 . . ?
C16 C18 H18A 109.4 . . ?
C17 C18 H18B 109.4 . . ?
C16 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
N3 C19 C20 104.2(2) . . ?
N3 C19 H19A 110.9 . . ?
C20 C19 H19A 110.9 . . ?
N3 C19 H19B 110.9 . . ?
C20 C19 H19B 110.9 . . ?
H19A C19 H19B 108.9 . . ?
C21 C20 C19 103.6(2) . . ?
C21 C20 H20A 111.0 . . ?
C19 C20 H20A 111.0 . . ?
C21 C20 H20B 111.0 . . ?
C19 C20 H20B 111.0 . . ?
H20A C20 H20B 109.0 . . ?
C20 C21 C22 104.9(2) . . ?
C20 C21 H21A 110.8 . . ?
C22 C21 H21A 110.8 . . ?
C20 C21 H21B 110.8 . . ?
C22 C21 H21B 110.8 . . ?
H21A C21 H21B 108.8 . . ?
N3 C22 C21 103.44(19) . . ?
N3 C22 H22A 111.1 . . ?
C21 C22 H22A 111.1 . . ?
N3 C22 H22B 111.1 . . ?
C21 C22 H22B 111.1 . . ?
H22A C22 H22B 109.0 . . ?
N3 C23 C28 127.7(2) . . ?
N3 C23 C24 117.8(2) . . ?
C28 C23 C24 114.5(2) . . ?
C25 C24 C23 123.3(2) . . ?
C25 C24 H24 118.4 . . ?
C23 C24 H24 118.4 . . ?
C24 C25 C26 121.7(3) . . ?
C24 C25 H25 119.1 . . ?
C26 C25 H25 119.1 . . ?
C27 C26 C25 116.1(2) . . ?
C27 C26 H26 122.0 . . ?
C25 C26 H26 122.0 . . ?
C26 C27 C28 124.5(2) . . ?
C26 C27 C30 125.7(2) . . ?
C28 C27 C30 109.8(2) . . ?
C27 C28 C23 119.9(2) . . ?
C27 C28 C29 105.9(2) . . ?
C23 C28 C29 134.2(2) . . ?
O3 C29 N4 120.6(2) . . ?
O3 C29 C28 132.0(2) . . ?
N4 C29 C28 107.5(2) . . ?
O4 C30 N4 125.6(2) . . ?
O4 C30 C27 128.5(2) . . ?
N4 C30 C27 106.0(2) . . ?
N4 C31 C32 113.1(2) . . ?
N4 C31 C33 111.39(19) . . ?
C32 C31 C33 111.1(2) . . ?
N4 C31 H31 107.0 . . ?
C32 C31 H31 107.0 . . ?
C33 C31 H31 107.0 . . ?
C31 C32 C35 110.0(2) . . ?
C31 C32 H32A 109.7 . . ?
C35 C32 H32A 109.7 . . ?
C31 C32 H32B 109.7 . . ?
C35 C32 H32B 109.7 . . ?
H32A C32 H32B 108.2 . . ?
C31 C33 C34 109.9(2) . . ?
C31 C33 H33A 109.7 . . ?
C34 C33 H33A 109.7 . . ?
C31 C33 H33B 109.7 . . ?
C34 C33 H33B 109.7 . . ?
H33A C33 H33B 108.2 . . ?
C36 C34 C33 110.7(2) . . ?
C36 C34 H34A 109.5 . . ?
C33 C34 H34A 109.5 . . ?
C36 C34 H34B 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 108.1 . . ?
C36 C35 C32 110.7(2) . . ?
C36 C35 H35A 109.5 . . ?
C32 C35 H35A 109.5 . . ?
C36 C35 H35B 109.5 . . ?
C32 C35 H35B 109.5 . . ?
H35A C35 H35B 108.1 . . ?
C34 C36 C35 111.7(2) . . ?
C34 C36 H36A 109.3 . . ?
C35 C36 H36A 109.3 . . ?
C34 C36 H36B 109.3 . . ?
C35 C36 H36B 109.3 . . ?
H36A C36 H36B 107.9 . . ?
N2 C12 C14 112.27(19) . . ?
N2 C12 C15 112.07(19) . . ?
C14 C12 C15 111.4(2) . . ?
N2 C12 H12 106.9 . . ?
C14 C12 H12 106.9 . . ?
C15 C12 H12 106.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 N1 C5 175.0(2) . . . . ?
C2 C1 N1 C4 -12.1(2) . . . . ?
N1 C1 C2 C3 31.8(2) . . . . ?
C1 C2 C3 C4 -40.1(3) . . . . ?
C5 N1 C4 C3 159.9(2) . . . . ?
C1 N1 C4 C3 -12.7(2) . . . . ?
C2 C3 C4 N1 32.5(3) . . . . ?
C4 N1 C5 C10 9.4(4) . . . . ?
C1 N1 C5 C10 -178.8(2) . . . . ?
C4 N1 C5 C6 -169.9(2) . . . . ?
C1 N1 C5 C6 1.9(3) . . . . ?
N1 C5 C6 C7 178.3(2) . . . . ?
C10 C5 C6 C7 -1.1(3) . . . . ?
C5 C6 C7 C8 0.1(4) . . . . ?
C6 C7 C8 C9 0.1(4) . . . . ?
C7 C8 C9 C10 0.8(4) . . . . ?
C7 C8 C9 C13 -180.0(2) . . . . ?
C8 C9 C10 C5 -1.9(4) . . . . ?
C13 C9 C10 C5 178.8(2) . . . . ?
C8 C9 C10 C11 175.8(2) . . . . ?
C13 C9 C10 C11 -3.5(3) . . . . ?
N1 C5 C10 C9 -177.5(2) . . . . ?
C6 C5 C10 C9 1.9(3) . . . . ?
N1 C5 C10 C11 5.6(4) . . . . ?
C6 C5 C10 C11 -175.0(2) . . . . ?
C13 N2 C11 O1 172.1(2) . . . . ?
C12 N2 C11 O1 -4.6(4) . . . . ?
C13 N2 C11 C10 -4.7(3) . . . . ?
C12 N2 C11 C10 178.6(2) . . . . ?
C9 C10 C11 O1 -171.3(3) . . . . ?
C5 C10 C11 O1 5.9(5) . . . . ?
C9 C10 C11 N2 5.0(3) . . . . ?
C5 C10 C11 N2 -177.8(2) . . . . ?
C11 N2 C13 O2 -176.8(2) . . . . ?
C12 N2 C13 O2 0.1(4) . . . . ?
C11 N2 C13 C9 2.6(2) . . . . ?
C12 N2 C13 C9 179.4(2) . . . . ?
C8 C9 C13 O2 0.7(4) . . . . ?
C10 C9 C13 O2 -180.0(2) . . . . ?
C8 C9 C13 N2 -178.6(2) . . . . ?
C10 C9 C13 N2 0.8(3) . . . . ?
C12 C14 C16 C18 54.9(3) . . . . ?
C12 C15 C17 C18 -55.7(3) . . . . ?
C15 C17 C18 C16 55.9(3) . . . . ?
C14 C16 C18 C17 -55.4(3) . . . . ?
C23 N3 C19 C20 174.3(2) . . . . ?
C22 N3 C19 C20 -11.2(3) . . . . ?
N3 C19 C20 C21 29.0(3) . . . . ?
C19 C20 C21 C22 -36.2(3) . . . . ?
C23 N3 C22 C21 163.3(2) . . . . ?
C19 N3 C22 C21 -10.9(3) . . . . ?
C20 C21 C22 N3 29.1(3) . . . . ?
C19 N3 C23 C28 -178.9(2) . . . . ?
C22 N3 C23 C28 7.5(4) . . . . ?
C19 N3 C23 C24 1.2(3) . . . . ?
C22 N3 C23 C24 -172.5(2) . . . . ?
N3 C23 C24 C25 179.8(2) . . . . ?
C28 C23 C24 C25 -0.1(3) . . . . ?
C23 C24 C25 C26 -0.4(4) . . . . ?
C24 C25 C26 C27 -0.2(4) . . . . ?
C25 C26 C27 C28 1.3(4) . . . . ?
C25 C26 C27 C30 -179.1(2) . . . . ?
C26 C27 C28 C23 -1.8(4) . . . . ?
C30 C27 C28 C23 178.6(2) . . . . ?
C26 C27 C28 C29 177.8(2) . . . . ?
C30 C27 C28 C29 -1.8(3) . . . . ?
N3 C23 C28 C27 -178.8(2) . . . . ?
C24 C23 C28 C27 1.1(3) . . . . ?
N3 C23 C28 C29 1.7(4) . . . . ?
C24 C23 C28 C29 -178.4(2) . . . . ?
C30 N4 C29 O3 177.7(2) . . . . ?
C31 N4 C29 O3 -6.5(4) . . . . ?
C30 N4 C29 C28 -1.2(3) . . . . ?
C31 N4 C29 C28 174.68(19) . . . . ?
C27 C28 C29 O3 -176.8(3) . . . . ?
C23 C28 C29 O3 2.7(5) . . . . ?
C27 C28 C29 N4 1.8(2) . . . . ?
C23 C28 C29 N4 -178.6(2) . . . . ?
C29 N4 C30 O4 179.4(2) . . . . ?
C31 N4 C30 O4 3.7(4) . . . . ?
C29 N4 C30 C27 0.1(2) . . . . ?
C31 N4 C30 C27 -175.6(2) . . . . ?
C26 C27 C30 O4 2.3(4) . . . . ?
C28 C27 C30 O4 -178.1(2) . . . . ?
C26 C27 C30 N4 -178.5(2) . . . . ?
C28 C27 C30 N4 1.1(3) . . . . ?
C30 N4 C31 C32 -60.8(3) . . . . ?
C29 N4 C31 C32 124.0(2) . . . . ?
C30 N4 C31 C33 65.1(3) . . . . ?
C29 N4 C31 C33 -110.1(2) . . . . ?
N4 C31 C32 C35 -175.5(2) . . . . ?
C33 C31 C32 C35 58.4(3) . . . . ?
N4 C31 C33 C34 174.7(2) . . . . ?
C32 C31 C33 C34 -58.3(3) . . . . ?
C31 C33 C34 C36 56.4(3) . . . . ?
C31 C32 C35 C36 -56.5(3) . . . . ?
C33 C34 C36 C35 -55.8(3) . . . . ?
C32 C35 C36 C34 55.9(3) . . . . ?
C13 N2 C12 C14 -109.6(2) . . . . ?
C11 N2 C12 C14 66.8(3) . . . . ?
C13 N2 C12 C15 124.1(2) . . . . ?
C11 N2 C12 C15 -59.5(3) . . . . ?
C16 C14 C12 N2 178.5(2) . . . . ?
C16 C14 C12 C15 -54.9(3) . . . . ?
C17 C15 C12 N2 -177.8(2) . . . . ?
C17 C15 C12 C14 55.4(3) . . . . ?

_refine_diff_density_max         0.241
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.052



