# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_5-109
_database_code_depnum_ccdc_archive 'CCDC 2218711'
loop_
_audit_author_name
_audit_author_address
'Tian Feng'
;Nankai University
China
;
_audit_update_record             
;
2022-11-10 deposited with the CCDC.	2023-03-06 downloaded from the CCDC.
;
_audit_creation_date             2022-11-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
(4R,7aR)-4-methyl-3,7-diphenyl-5,6,7,7a-tetrahydrofuro[2,3-b]pyridin-2(4H)-one
_chemical_formula_moiety         'C20 H19 N O2'
_chemical_formula_sum            'C20 H19 N O2'
_chemical_formula_weight         305.36
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           78
_space_group_name_H-M_alt        'P 43'
_space_group_name_Hall           'P 4cw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'

_cell_length_a                   9.58017(5)
_cell_length_b                   9.58017(5)
_cell_length_c                   33.7964(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3101.82(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    100.01(16)
_cell_measurement_theta_max      75.7550
_cell_measurement_theta_min      4.7710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            16868
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.945
_diffrn_reflns_theta_min         4.616
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(16)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00 -28.00   0.50    0.60    --    0.00 -25.00 -15.00   50
  2  ω    106.00 131.00   0.50    2.00    --  101.30  25.00 148.00   50
  3  ω     26.00  75.00   0.50    2.00    --  101.30 -25.00 -15.00   98
  4  ω    -36.00  39.00   0.50    0.60    --    0.00  82.00-150.00  150
  5  ω     76.00 191.00   0.50    2.00    --  101.30  38.00 -60.00  230
  6  ω     86.00 191.00   0.50    2.00    --  101.30  82.00  60.00  210
  7  ω     58.00  85.00   0.50    0.60    --    0.00  24.00 148.00   54
  8  ω    151.00 185.00   0.50    1.50    --  101.30  19.00 120.00   68
  9  ω     13.00  40.00   0.50    1.50    --  101.30 -38.00 -30.00   54
 10  ω     64.00 127.00   0.50    1.50    --  101.30 -38.00 -30.00  126
 11  ω     76.00 127.00   0.50    1.50    --  101.30  38.00 -30.00  102
 12  ω    144.00 170.00   0.50    1.50    --  101.30  38.00 -30.00   52
 13  ω     74.00 148.00   0.50    1.50    --  101.30  19.00 120.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0049067000
_diffrn_orient_matrix_UB_12      0.0204369000
_diffrn_orient_matrix_UB_13      0.0451985000
_diffrn_orient_matrix_UB_21      -0.1532732000
_diffrn_orient_matrix_UB_22      0.0473320000
_diffrn_orient_matrix_UB_23      -0.0030589000
_diffrn_orient_matrix_UB_31      -0.0482810000
_diffrn_orient_matrix_UB_32      -0.1523290000
_diffrn_orient_matrix_UB_33      0.0051230000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.926
_reflns_number_gt                6022
_reflns_number_total             6166
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 2683 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.28(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         6166
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.142
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0074P)²+4.1257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1247
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10), C29(H29), C32(H32)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C27(H27A,H27B), C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C36(H36),
  C37(H37), C38(H38), C39(H39), C40(H40)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6445(3) 0.6537(3) 0.48334(9) 0.0240(6) Uani 1 1 d . . . . .
O2 O 0.7370(4) 0.5281(3) 0.43446(9) 0.0289(7) Uani 1 1 d . . . . .
N1 N 0.6422(4) 0.8606(4) 0.52347(11) 0.0219(7) Uani 1 1 d . . . . .
C1 C 0.5252(4) 0.8792(5) 0.54836(12) 0.0214(8) Uani 1 1 d . . . . .
C2 C 0.4979(5) 1.0069(5) 0.56607(12) 0.0239(9) Uani 1 1 d . . . . .
H2 H 0.559056 1.083544 0.561811 0.029 Uiso 1 1 calc R U . . .
C3 C 0.3803(5) 1.0229(5) 0.59025(13) 0.0252(9) Uani 1 1 d . . . . .
H3 H 0.361765 1.110914 0.602073 0.030 Uiso 1 1 calc R U . . .
C4 C 0.2907(5) 0.9125(5) 0.59715(13) 0.0257(9) Uani 1 1 d . . . . .
H4 H 0.211605 0.923835 0.613794 0.031 Uiso 1 1 calc R U . . .
C5 C 0.3179(5) 0.7861(5) 0.57952(13) 0.0255(9) Uani 1 1 d . . . . .
H5 H 0.256434 0.709861 0.583944 0.031 Uiso 1 1 calc R U . . .
C6 C 0.4333(4) 0.7680(5) 0.55546(12) 0.0223(9) Uani 1 1 d . . . . .
H6 H 0.450464 0.679628 0.543657 0.027 Uiso 1 1 calc R U . . .
C7 C 0.6989(5) 0.7243(4) 0.51857(13) 0.0226(9) Uani 1 1 d . . . . .
H7 H 0.676770 0.667025 0.542493 0.027 Uiso 1 1 calc R U . . .
C8 C 0.7419(5) 0.9735(5) 0.51527(13) 0.0240(9) Uani 1 1 d . . . . .
H8A H 0.694916 1.064857 0.518465 0.029 Uiso 1 1 calc R U . . .
H8B H 0.774998 0.966228 0.487601 0.029 Uiso 1 1 calc R U . . .
C9 C 0.8662(5) 0.9648(5) 0.54342(14) 0.0274(9) Uani 1 1 d . . . . .
H9A H 0.834527 0.983089 0.570822 0.033 Uiso 1 1 calc R U . . .
H9B H 0.935682 1.036969 0.536272 0.033 Uiso 1 1 calc R U . . .
C10 C 0.9356(5) 0.8170(5) 0.54123(13) 0.0239(9) Uani 1 1 d . . . . .
H10 H 1.032992 0.827518 0.531040 0.029 Uiso 1 1 calc R U . . .
C11 C 0.8544(5) 0.7287(4) 0.51287(12) 0.0212(9) Uani 1 1 d . . . . .
C12 C 0.9411(5) 0.7474(5) 0.58215(13) 0.0280(10) Uani 1 1 d . . . . .
H12A H 0.990126 0.808785 0.600733 0.042 Uiso 1 1 calc R U . . .
H12B H 0.990776 0.658309 0.580172 0.042 Uiso 1 1 calc R U . . .
H12C H 0.845871 0.730877 0.591656 0.042 Uiso 1 1 calc R U . . .
C13 C 0.8869(4) 0.6540(4) 0.48027(12) 0.0210(8) Uani 1 1 d . . . . .
C14 C 0.7550(5) 0.6035(4) 0.46264(13) 0.0236(9) Uani 1 1 d . . . . .
C15 C 1.0257(5) 0.6310(4) 0.46199(13) 0.0222(9) Uani 1 1 d . . . . .
C16 C 1.1473(5) 0.6307(4) 0.48468(13) 0.0236(9) Uani 1 1 d . . . . .
H16 H 1.140956 0.638406 0.512651 0.028 Uiso 1 1 calc R U . . .
C17 C 1.2782(5) 0.6194(5) 0.46686(14) 0.0272(9) Uani 1 1 d . . . . .
H17 H 1.360592 0.620872 0.482481 0.033 Uiso 1 1 calc R U . . .
C18 C 1.2866(5) 0.6058(5) 0.42579(14) 0.0300(10) Uani 1 1 d . . . . .
H18 H 1.375203 0.599097 0.413335 0.036 Uiso 1 1 calc R U . . .
C19 C 1.1671(5) 0.6020(5) 0.40333(14) 0.0280(10) Uani 1 1 d . . . . .
H19 H 1.173494 0.590466 0.375469 0.034 Uiso 1 1 calc R U . . .
C20 C 1.0365(5) 0.6149(5) 0.42116(13) 0.0257(9) Uani 1 1 d . . . . .
H20 H 0.954516 0.612620 0.405377 0.031 Uiso 1 1 calc R U . . .
O3 O 1.1275(3) 1.3189(3) 0.51923(9) 0.0244(6) Uani 1 1 d . . . . .
O4 O 1.2112(4) 1.4352(3) 0.57166(9) 0.0305(7) Uani 1 1 d . . . . .
N2 N 1.1339(4) 1.1220(4) 0.47544(11) 0.0229(8) Uani 1 1 d . . . . .
C21 C 1.0211(5) 1.1056(5) 0.44918(12) 0.0227(9) Uani 1 1 d . . . . .
C22 C 1.0011(5) 0.9814(4) 0.42746(13) 0.0244(9) Uani 1 1 d . . . . .
H22 H 1.065812 0.906790 0.430034 0.029 Uiso 1 1 calc R U . . .
C23 C 0.8875(5) 0.9677(5) 0.40244(14) 0.0285(10) Uani 1 1 d . . . . .
H23 H 0.875041 0.883239 0.388133 0.034 Uiso 1 1 calc R U . . .
C24 C 0.7917(5) 1.0746(5) 0.39784(13) 0.0269(9) Uani 1 1 d . . . . .
H24 H 0.714115 1.064239 0.380566 0.032 Uiso 1 1 calc R U . . .
C25 C 0.8113(5) 1.1971(5) 0.41898(13) 0.0256(9) Uani 1 1 d . . . . .
H25 H 0.746677 1.271509 0.415881 0.031 Uiso 1 1 calc R U . . .
C26 C 0.9224(4) 1.2130(5) 0.44432(13) 0.0225(9) Uani 1 1 d . . . . .
H26 H 0.932608 1.297500 0.458739 0.027 Uiso 1 1 calc R U . . .
C27 C 1.2335(5) 1.0080(4) 0.48311(13) 0.0245(9) Uani 1 1 d . . . . .
H27A H 1.188576 0.917141 0.477444 0.029 Uiso 1 1 calc R U . . .
H27B H 1.261247 1.009059 0.511325 0.029 Uiso 1 1 calc R U . . .
C28 C 1.3619(5) 1.0253(5) 0.45721(14) 0.0280(10) Uani 1 1 d . . . . .
H28A H 1.335668 1.010356 0.429195 0.034 Uiso 1 1 calc R U . . .
H28B H 1.431840 0.953734 0.464465 0.034 Uiso 1 1 calc R U . . .
C29 C 1.4278(5) 1.1730(5) 0.46180(13) 0.0228(9) Uani 1 1 d . . . . .
H29 H 1.523968 1.162708 0.472966 0.027 Uiso 1 1 calc R U . . .
C30 C 1.4377(5) 1.2482(5) 0.42188(13) 0.0279(10) Uani 1 1 d . . . . .
H30A H 1.492560 1.191509 0.403410 0.042 Uiso 1 1 calc R U . . .
H30B H 1.483227 1.338916 0.425529 0.042 Uiso 1 1 calc R U . . .
H30C H 1.343730 1.262271 0.411157 0.042 Uiso 1 1 calc R U . . .
C31 C 1.3406(4) 1.2563(4) 0.49037(12) 0.0194(8) Uani 1 1 d . . . . .
C32 C 1.1869(5) 1.2572(4) 0.48324(12) 0.0220(8) Uani 1 1 d . . . . .
H32 H 1.165866 1.319330 0.460217 0.026 Uiso 1 1 calc R U . . .
C33 C 1.2335(5) 1.3672(5) 0.54180(12) 0.0239(9) Uani 1 1 d . . . . .
C34 C 1.3701(5) 1.3262(4) 0.52402(12) 0.0218(9) Uani 1 1 d . . . . .
C35 C 1.5054(5) 1.3537(4) 0.54311(13) 0.0223(9) Uani 1 1 d . . . . .
C36 C 1.5178(5) 1.3699(5) 0.58415(13) 0.0264(9) Uani 1 1 d . . . . .
H36 H 1.435961 1.370713 0.600042 0.032 Uiso 1 1 calc R U . . .
C37 C 1.6466(5) 1.3846(5) 0.60190(14) 0.0311(11) Uani 1 1 d . . . . .
H37 H 1.652557 1.396603 0.629753 0.037 Uiso 1 1 calc R U . . .
C38 C 1.7678(5) 1.3819(5) 0.57930(15) 0.0303(10) Uani 1 1 d . . . . .
H38 H 1.856538 1.387840 0.591736 0.036 Uiso 1 1 calc R U . . .
C39 C 1.7584(5) 1.3704(5) 0.53847(14) 0.0258(9) Uani 1 1 d . . . . .
H39 H 1.840863 1.371187 0.522836 0.031 Uiso 1 1 calc R U . . .
C40 C 1.6292(5) 1.3577(4) 0.52042(13) 0.0245(9) Uani 1 1 d . . . . .
H40 H 1.623746 1.351638 0.492410 0.029 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 1.465(5) . ?
O1 C14 1.356(5) . ?
O2 C14 1.207(5) . ?
N1 C1 1.412(5) . ?
N1 C7 1.424(5) . ?
N1 C8 1.469(5) . ?
C1 C2 1.387(6) . ?
C1 C6 1.403(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.401(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.375(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(6) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C11 1.503(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.526(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.566(6) . ?
C10 H10 1.0000 . ?
C10 C11 1.497(6) . ?
C10 C12 1.536(6) . ?
C11 C13 1.350(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.479(6) . ?
C13 C15 1.483(6) . ?
C15 C16 1.395(6) . ?
C15 C20 1.392(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.395(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.397(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.374(7) . ?
C19 H19 0.9500 . ?
C19 C20 1.394(7) . ?
C20 H20 0.9500 . ?
O3 C32 1.467(5) . ?
O3 C33 1.351(5) . ?
O4 C33 1.220(5) . ?
N2 C21 1.407(6) . ?
N2 C27 1.473(5) . ?
N2 C32 1.416(5) . ?
C21 C22 1.412(6) . ?
C21 C26 1.407(6) . ?
C22 H22 0.9500 . ?
C22 C23 1.385(7) . ?
C23 H23 0.9500 . ?
C23 C24 1.384(7) . ?
C24 H24 0.9500 . ?
C24 C25 1.387(6) . ?
C25 H25 0.9500 . ?
C25 C26 1.375(6) . ?
C26 H26 0.9500 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.519(7) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.557(6) . ?
C29 H29 1.0000 . ?
C29 C30 1.533(6) . ?
C29 C31 1.506(6) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C32 1.493(6) . ?
C31 C34 1.350(6) . ?
C32 H32 1.0000 . ?
C33 C34 1.492(6) . ?
C34 C35 1.472(6) . ?
C35 C36 1.401(6) . ?
C35 C40 1.412(6) . ?
C36 H36 0.9500 . ?
C36 C37 1.380(7) . ?
C37 H37 0.9500 . ?
C37 C38 1.390(7) . ?
C38 H38 0.9500 . ?
C38 C39 1.387(7) . ?
C39 H39 0.9500 . ?
C39 C40 1.386(6) . ?
C40 H40 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
C14 O1 C7 107.8(3) . . ?
C1 N1 C7 119.2(4) . . ?
C1 N1 C8 122.4(3) . . ?
C7 N1 C8 113.9(3) . . ?
C2 C1 N1 121.2(4) . . ?
C2 C1 C6 118.6(4) . . ?
C6 C1 N1 120.3(4) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.0(4) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.0(4) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 118.9(4) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.1(4) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.5(4) . . ?
C5 C6 H6 119.8 . . ?
O1 C7 H7 109.2 . . ?
O1 C7 C11 105.1(3) . . ?
N1 C7 O1 112.5(4) . . ?
N1 C7 H7 109.2 . . ?
N1 C7 C11 111.6(3) . . ?
C11 C7 H7 109.2 . . ?
N1 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
N1 C8 C9 110.4(4) . . ?
H8A C8 H8B 108.1 . . ?
C9 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 C10 110.6(4) . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C9 C10 H10 108.8 . . ?
C11 C10 C9 108.7(4) . . ?
C11 C10 H10 108.8 . . ?
C11 C10 C12 110.4(4) . . ?
C12 C10 C9 111.4(4) . . ?
C12 C10 H10 108.8 . . ?
C10 C11 C7 116.7(4) . . ?
C13 C11 C7 108.6(4) . . ?
C13 C11 C10 134.6(4) . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 C14 107.7(4) . . ?
C11 C13 C15 128.8(4) . . ?
C14 C13 C15 123.4(4) . . ?
O1 C14 C13 110.0(4) . . ?
O2 C14 O1 120.5(4) . . ?
O2 C14 C13 129.4(4) . . ?
C16 C15 C13 121.3(4) . . ?
C20 C15 C13 119.8(4) . . ?
C20 C15 C16 118.8(4) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.9(4) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C18 119.2(4) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.2(4) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.4(4) . . ?
C20 C19 H19 119.8 . . ?
C15 C20 C19 120.4(4) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C33 O3 C32 108.3(3) . . ?
C21 N2 C27 121.7(4) . . ?
C21 N2 C32 119.7(4) . . ?
C32 N2 C27 114.4(4) . . ?
N2 C21 C22 121.8(4) . . ?
N2 C21 C26 120.5(4) . . ?
C26 C21 C22 117.7(4) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.3(4) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 119.3 . . ?
C24 C23 C22 121.3(4) . . ?
C24 C23 H23 119.3 . . ?
C23 C24 H24 120.7 . . ?
C23 C24 C25 118.6(4) . . ?
C25 C24 H24 120.7 . . ?
C24 C25 H25 119.3 . . ?
C26 C25 C24 121.3(4) . . ?
C26 C25 H25 119.3 . . ?
C21 C26 H26 119.6 . . ?
C25 C26 C21 120.8(4) . . ?
C25 C26 H26 119.6 . . ?
N2 C27 H27A 109.7 . . ?
N2 C27 H27B 109.7 . . ?
N2 C27 C28 110.0(4) . . ?
H27A C27 H27B 108.2 . . ?
C28 C27 H27A 109.7 . . ?
C28 C27 H27B 109.7 . . ?
C27 C28 H28A 109.3 . . ?
C27 C28 H28B 109.3 . . ?
C27 C28 C29 111.7(4) . . ?
H28A C28 H28B 107.9 . . ?
C29 C28 H28A 109.3 . . ?
C29 C28 H28B 109.3 . . ?
C28 C29 H29 108.8 . . ?
C30 C29 C28 111.4(4) . . ?
C30 C29 H29 108.8 . . ?
C31 C29 C28 108.7(4) . . ?
C31 C29 H29 108.8 . . ?
C31 C29 C30 110.5(4) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C32 C31 C29 116.6(4) . . ?
C34 C31 C29 133.4(4) . . ?
C34 C31 C32 109.9(4) . . ?
O3 C32 C31 104.5(3) . . ?
O3 C32 H32 109.1 . . ?
N2 C32 O3 112.6(4) . . ?
N2 C32 C31 112.2(4) . . ?
N2 C32 H32 109.1 . . ?
C31 C32 H32 109.1 . . ?
O3 C33 C34 110.0(4) . . ?
O4 C33 O3 121.2(4) . . ?
O4 C33 C34 128.8(4) . . ?
C31 C34 C33 106.6(4) . . ?
C31 C34 C35 130.0(4) . . ?
C35 C34 C33 123.3(4) . . ?
C36 C35 C34 121.9(4) . . ?
C36 C35 C40 117.6(4) . . ?
C40 C35 C34 120.4(4) . . ?
C35 C36 H36 119.4 . . ?
C37 C36 C35 121.1(4) . . ?
C37 C36 H36 119.4 . . ?
C36 C37 H37 119.8 . . ?
C36 C37 C38 120.4(4) . . ?
C38 C37 H37 119.8 . . ?
C37 C38 H38 120.2 . . ?
C39 C38 C37 119.6(4) . . ?
C39 C38 H38 120.2 . . ?
C38 C39 H39 119.9 . . ?
C40 C39 C38 120.2(4) . . ?
C40 C39 H39 119.9 . . ?
C35 C40 H40 119.5 . . ?
C39 C40 C35 120.9(4) . . ?
C39 C40 H40 119.5 . . ?

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
O1 C7 C11 C10 169.8(3) . . . . ?
O1 C7 C11 C13 -6.5(4) . . . . ?
N1 C1 C2 C3 179.2(4) . . . . ?
N1 C1 C6 C5 -179.4(4) . . . . ?
N1 C7 C11 C10 47.6(5) . . . . ?
N1 C7 C11 C13 -128.7(4) . . . . ?
N1 C8 C9 C10 55.0(5) . . . . ?
C1 N1 C7 O1 95.2(5) . . . . ?
C1 N1 C7 C11 -146.9(4) . . . . ?
C1 N1 C8 C9 94.9(5) . . . . ?
C1 C2 C3 C4 0.6(7) . . . . ?
C2 C1 C6 C5 0.2(6) . . . . ?
C2 C3 C4 C5 -0.7(7) . . . . ?
C3 C4 C5 C6 0.5(7) . . . . ?
C4 C5 C6 C1 -0.3(7) . . . . ?
C6 C1 C2 C3 -0.4(6) . . . . ?
C7 O1 C14 O2 172.1(4) . . . . ?
C7 O1 C14 C13 -7.3(4) . . . . ?
C7 N1 C1 C2 155.3(4) . . . . ?
C7 N1 C1 C6 -25.1(6) . . . . ?
C7 N1 C8 C9 -60.9(5) . . . . ?
C7 C11 C13 C14 2.3(5) . . . . ?
C7 C11 C13 C15 178.1(4) . . . . ?
C8 N1 C1 C2 0.7(6) . . . . ?
C8 N1 C1 C6 -179.7(4) . . . . ?
C8 N1 C7 O1 -108.1(4) . . . . ?
C8 N1 C7 C11 9.8(5) . . . . ?
C8 C9 C10 C11 -1.8(5) . . . . ?
C8 C9 C10 C12 -123.7(4) . . . . ?
C9 C10 C11 C7 -49.8(5) . . . . ?
C9 C10 C11 C13 125.4(5) . . . . ?
C10 C11 C13 C14 -173.1(5) . . . . ?
C10 C11 C13 C15 2.6(8) . . . . ?
C11 C13 C14 O1 3.2(5) . . . . ?
C11 C13 C14 O2 -176.2(4) . . . . ?
C11 C13 C15 C16 29.4(7) . . . . ?
C11 C13 C15 C20 -148.0(5) . . . . ?
C12 C10 C11 C7 72.6(5) . . . . ?
C12 C10 C11 C13 -112.2(5) . . . . ?
C13 C15 C16 C17 -175.2(4) . . . . ?
C13 C15 C20 C19 176.0(4) . . . . ?
C14 O1 C7 N1 130.0(4) . . . . ?
C14 O1 C7 C11 8.4(4) . . . . ?
C14 C13 C15 C16 -155.4(4) . . . . ?
C14 C13 C15 C20 27.2(6) . . . . ?
C15 C13 C14 O1 -172.9(4) . . . . ?
C15 C13 C14 O2 7.7(7) . . . . ?
C15 C16 C17 C18 -1.1(7) . . . . ?
C16 C15 C20 C19 -1.5(6) . . . . ?
C16 C17 C18 C19 -0.8(7) . . . . ?
C17 C18 C19 C20 1.5(7) . . . . ?
C18 C19 C20 C15 -0.3(7) . . . . ?
C20 C15 C16 C17 2.2(6) . . . . ?
O3 C33 C34 C31 1.4(5) . . . . ?
O3 C33 C34 C35 -175.2(4) . . . . ?
O4 C33 C34 C31 -177.7(4) . . . . ?
O4 C33 C34 C35 5.7(7) . . . . ?
N2 C21 C22 C23 178.8(4) . . . . ?
N2 C21 C26 C25 -179.4(4) . . . . ?
N2 C27 C28 C29 53.5(5) . . . . ?
C21 N2 C27 C28 96.5(5) . . . . ?
C21 N2 C32 O3 95.8(5) . . . . ?
C21 N2 C32 C31 -146.6(4) . . . . ?
C21 C22 C23 C24 0.4(7) . . . . ?
C22 C21 C26 C25 -0.6(6) . . . . ?
C22 C23 C24 C25 -0.1(7) . . . . ?
C23 C24 C25 C26 -0.6(7) . . . . ?
C24 C25 C26 C21 0.9(7) . . . . ?
C26 C21 C22 C23 0.0(7) . . . . ?
C27 N2 C21 C22 -2.9(6) . . . . ?
C27 N2 C21 C26 175.9(4) . . . . ?
C27 N2 C32 O3 -106.9(4) . . . . ?
C27 N2 C32 C31 10.7(5) . . . . ?
C27 C28 C29 C30 -123.2(4) . . . . ?
C27 C28 C29 C31 -1.3(5) . . . . ?
C28 C29 C31 C32 -49.1(5) . . . . ?
C28 C29 C31 C34 125.5(5) . . . . ?
C29 C31 C32 O3 168.4(3) . . . . ?
C29 C31 C32 N2 46.1(5) . . . . ?
C29 C31 C34 C33 -170.9(4) . . . . ?
C29 C31 C34 C35 5.3(8) . . . . ?
C30 C29 C31 C32 73.3(5) . . . . ?
C30 C29 C31 C34 -112.1(5) . . . . ?
C31 C34 C35 C36 -150.7(5) . . . . ?
C31 C34 C35 C40 26.0(7) . . . . ?
C32 O3 C33 O4 173.0(4) . . . . ?
C32 O3 C33 C34 -6.2(4) . . . . ?
C32 N2 C21 C22 152.7(4) . . . . ?
C32 N2 C21 C26 -28.5(6) . . . . ?
C32 N2 C27 C28 -60.3(5) . . . . ?
C32 C31 C34 C33 3.9(5) . . . . ?
C32 C31 C34 C35 -179.8(4) . . . . ?
C33 O3 C32 N2 130.3(4) . . . . ?
C33 O3 C32 C31 8.2(4) . . . . ?
C33 C34 C35 C36 25.0(6) . . . . ?
C33 C34 C35 C40 -158.2(4) . . . . ?
C34 C31 C32 O3 -7.5(4) . . . . ?
C34 C31 C32 N2 -129.8(4) . . . . ?
C34 C35 C36 C37 174.8(4) . . . . ?
C34 C35 C40 C39 -173.8(4) . . . . ?
C35 C36 C37 C38 -0.8(7) . . . . ?
C36 C35 C40 C39 3.1(6) . . . . ?
C36 C37 C38 C39 2.8(7) . . . . ?
C37 C38 C39 C40 -1.8(7) . . . . ?
C38 C39 C40 C35 -1.2(7) . . . . ?
C40 C35 C36 C37 -2.1(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.466
_oxdiff_exptl_absorpt_empirical_full_min 0.706
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane, Hexane'
