# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

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

data_MMOCC
_database_code_depnum_ccdc_archive 'CCDC 1976271'
loop_
_audit_author_name
_audit_author_address
'Hadi Arman'
;UTSA
United States of America
;
_audit_update_record             
;
2020-01-08 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
_audit_creation_date             2020-01-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
(1R,2R,6R)-2-(4-methoxyphenyl)-6-[(E)-4-methoxystyryl]-4-oxocyclohexane-1-carbaldehyde
_chemical_formula_moiety         'C23 H24 O4'
_chemical_formula_sum            'C23 H24 O4'
_chemical_formula_weight         364.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20O4
_chemical_oxdiff_usercomment     PB-3-OMe
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   29.4116(11)
_cell_length_b                   6.0927(2)
_cell_length_c                   10.9457(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.118(3)
_cell_angle_gamma                90
_cell_volume                     1936.64(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9157
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      23.6490
_cell_measurement_theta_min      2.7700
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.033
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            46751
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.046
_diffrn_reflns_theta_max         25.046
_diffrn_reflns_theta_min         2.806
_diffrn_ambient_temperature      98(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -96.00  17.00   1.00   29.00    --   -7.50 -38.00 -90.00  113
  2  ω    -46.00  81.00   1.00   29.00    --   -7.50  19.00-180.00  127
  3  ω    -96.00  31.00   1.00   29.00    --   -7.50 -19.00 -30.00  127
  4  ω    -26.00  94.00   1.00   29.00    --    4.20  57.00-120.00  120
  5  ω    -40.00  81.00   1.00   29.00    --   -7.50  72.00-120.00  121
  6  ω    -40.00  81.00   1.00   29.00    --   -7.50  72.00  30.00  121
  7  ω    -96.00 -35.00   1.00   29.00    --   -7.50 -72.00 120.00   61
  8  ω    -37.00  81.00   1.00   29.00    --   -7.50  57.00   0.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0070352000
_diffrn_orient_matrix_UB_12      0.1047881000
_diffrn_orient_matrix_UB_13      0.0241512000
_diffrn_orient_matrix_UB_21      -0.0232714000
_diffrn_orient_matrix_UB_22      0.0353478000
_diffrn_orient_matrix_UB_23      -0.0095798000
_diffrn_orient_matrix_UB_31      -0.0023099000
_diffrn_orient_matrix_UB_32      -0.0363858000
_diffrn_orient_matrix_UB_33      0.0602654000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3296
_reflns_number_total             3423
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3423
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0680
_refine_ls_restrained_S_all      1.043
_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)+(0.0150P)²+3.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1175
_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:
 C4(H4), C3(H3), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C20(H20), C16(H16), C22(H22), C7(H7), C8(H8), C21(H21), C10(H10),
 C14(H14), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C15(H15A,H15B,H15C)
;
_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
O4 O 0.46406(6) 0.4094(3) 0.88970(15) 0.0289(4) Uani 1 1 d . . . . .
O1 O 0.24192(6) 0.0637(3) 0.41850(15) 0.0335(4) Uani 1 1 d . . . . .
O2 O 0.03600(6) 0.9555(3) 0.89257(18) 0.0409(5) Uani 1 1 d . . . . .
O3 O 0.29119(9) 0.9565(3) 0.73725(19) 0.0578(7) Uani 1 1 d . . . . .
C19 C 0.43440(8) 0.4884(4) 0.7900(2) 0.0224(5) Uani 1 1 d . . . . .
C17 C 0.36140(8) 0.5114(4) 0.6548(2) 0.0237(5) Uani 1 1 d . . . . .
C18 C 0.38910(8) 0.4205(4) 0.7572(2) 0.0227(5) Uani 1 1 d . . . . .
H18 H 0.376904 0.311401 0.804920 0.027 Uiso 1 1 calc R . . . .
C4 C 0.27748(8) 0.6288(4) 0.6173(2) 0.0230(5) Uani 1 1 d . . . . .
H4 H 0.281408 0.723719 0.545182 0.028 Uiso 1 1 calc R . . . .
C3 C 0.22758(8) 0.5392(4) 0.5977(2) 0.0241(5) Uani 1 1 d . . . . .
H3 H 0.225622 0.428193 0.663990 0.029 Uiso 1 1 calc R . . . .
C20 C 0.45269(8) 0.6470(4) 0.7205(2) 0.0256(5) Uani 1 1 d . . . . .
H20 H 0.483653 0.694149 0.743583 0.031 Uiso 1 1 calc R . . . .
C6 C 0.30333(8) 0.2992(4) 0.5057(2) 0.0254(5) Uani 1 1 d . . . . .
H6A H 0.315001 0.380758 0.438870 0.030 Uiso 1 1 calc R . . . .
H6B H 0.321338 0.161746 0.520140 0.030 Uiso 1 1 calc R . . . .
C5 C 0.31164(8) 0.4374(4) 0.6239(2) 0.0242(5) Uani 1 1 d . . . . .
H5 H 0.305516 0.340248 0.693148 0.029 Uiso 1 1 calc R . . . .
C16 C 0.28667(8) 0.7638(4) 0.7325(2) 0.0277(6) Uani 1 1 d . . . . .
H16 H 0.289104 0.687743 0.809036 0.033 Uiso 1 1 calc R . . . .
C22 C 0.37997(9) 0.6690(4) 0.5847(2) 0.0288(6) Uani 1 1 d . . . . .
H22 H 0.361481 0.731318 0.514198 0.035 Uiso 1 1 calc R . . . .
C7 C 0.19258(8) 0.7122(4) 0.6086(2) 0.0270(5) Uani 1 1 d . . . . .
H7 H 0.188203 0.823733 0.547181 0.032 Uiso 1 1 calc R . . . .
C8 C 0.16728(8) 0.7205(4) 0.6978(2) 0.0284(6) Uani 1 1 d . . . . .
H8 H 0.172120 0.606791 0.757843 0.034 Uiso 1 1 calc R . . . .
C1 C 0.25344(8) 0.2413(4) 0.4629(2) 0.0249(5) Uani 1 1 d . . . . .
C9 C 0.13220(8) 0.8872(4) 0.7150(2) 0.0298(6) Uani 1 1 d . . . . .
C21 C 0.42566(9) 0.7357(4) 0.6179(2) 0.0303(6) Uani 1 1 d . . . . .
H21 H 0.438201 0.842711 0.569622 0.036 Uiso 1 1 calc R . . . .
C2 C 0.21860(8) 0.4191(4) 0.4734(2) 0.0288(6) Uani 1 1 d . . . . .
H2A H 0.187463 0.353080 0.462588 0.035 Uiso 1 1 calc R . . . .
H2B H 0.219200 0.526705 0.405865 0.035 Uiso 1 1 calc R . . . .
C10 C 0.10205(8) 0.8411(4) 0.7983(2) 0.0304(6) Uani 1 1 d . . . . .
H10 H 0.105052 0.707876 0.843956 0.036 Uiso 1 1 calc R . . . .
C11 C 0.06775(8) 0.9897(5) 0.8145(2) 0.0328(6) Uani 1 1 d . . . . .
C23 C 0.44945(9) 0.2254(4) 0.9543(2) 0.0339(6) Uani 1 1 d . . . . .
H23A H 0.441178 0.104196 0.896211 0.051 Uiso 1 1 calc GR . . . .
H23B H 0.422611 0.266693 0.992078 0.051 Uiso 1 1 calc GR . . . .
H23C H 0.474532 0.179099 1.019075 0.051 Uiso 1 1 calc GR . . . .
C14 C 0.12790(9) 1.0846(5) 0.6512(3) 0.0394(7) Uani 1 1 d . . . . .
H14 H 0.148589 1.118948 0.595572 0.047 Uiso 1 1 calc R . . . .
C12 C 0.06336(9) 1.1857(5) 0.7498(3) 0.0401(7) Uani 1 1 d . . . . .
H12 H 0.039863 1.287079 0.761328 0.048 Uiso 1 1 calc R . . . .
C15 C 0.03849(10) 0.7547(5) 0.9615(3) 0.0457(7) Uani 1 1 d . . . . .
H15A H 0.033727 0.630246 0.904186 0.069 Uiso 1 1 calc GR . . . .
H15B H 0.014598 0.754153 1.014548 0.069 Uiso 1 1 calc GR . . . .
H15C H 0.068855 0.742448 1.012898 0.069 Uiso 1 1 calc GR . . . .
C13 C 0.09340(10) 1.2329(5) 0.6683(3) 0.0458(8) Uani 1 1 d . . . . .
H13 H 0.090514 1.367244 0.623608 0.055 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C19 1.372(3) . ?
O4 C23 1.427(3) . ?
O1 C1 1.212(3) . ?
O2 C11 1.378(3) . ?
O2 C15 1.433(4) . ?
O3 C16 1.182(3) . ?
C19 C18 1.387(3) . ?
C19 C20 1.389(3) . ?
C17 C18 1.392(3) . ?
C17 C5 1.517(3) . ?
C17 C22 1.393(3) . ?
C18 H18 0.9500 . ?
C4 H4 1.0000 . ?
C4 C3 1.549(3) . ?
C4 C5 1.534(3) . ?
C4 C16 1.494(3) . ?
C3 H3 1.0000 . ?
C3 C7 1.491(3) . ?
C3 C2 1.531(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.379(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.531(3) . ?
C6 C1 1.510(3) . ?
C5 H5 1.0000 . ?
C16 H16 0.9500 . ?
C22 H22 0.9500 . ?
C22 C21 1.396(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.319(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.481(3) . ?
C1 C2 1.508(3) . ?
C9 C10 1.398(4) . ?
C9 C14 1.386(4) . ?
C21 H21 0.9500 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C10 H10 0.9500 . ?
C10 C11 1.388(4) . ?
C11 C12 1.384(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C14 H14 0.9500 . ?
C14 C13 1.393(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C13 H13 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
C19 O4 C23 117.82(19) . . ?
C11 O2 C15 118.2(2) . . ?
O4 C19 C18 124.4(2) . . ?
O4 C19 C20 115.3(2) . . ?
C18 C19 C20 120.4(2) . . ?
C18 C17 C5 118.8(2) . . ?
C18 C17 C22 119.1(2) . . ?
C22 C17 C5 122.1(2) . . ?
C19 C18 C17 120.3(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C3 C4 H4 108.7 . . ?
C5 C4 H4 108.7 . . ?
C5 C4 C3 109.74(19) . . ?
C16 C4 H4 108.7 . . ?
C16 C4 C3 110.61(19) . . ?
C16 C4 C5 110.44(19) . . ?
C4 C3 H3 107.5 . . ?
C7 C3 C4 113.0(2) . . ?
C7 C3 H3 107.5 . . ?
C7 C3 C2 112.62(19) . . ?
C2 C3 C4 108.54(19) . . ?
C2 C3 H3 107.5 . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.7(2) . . ?
C21 C20 H20 120.2 . . ?
H6A C6 H6B 107.6 . . ?
C5 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
C1 C6 H6A 108.7 . . ?
C1 C6 H6B 108.7 . . ?
C1 C6 C5 114.10(19) . . ?
C17 C5 C4 112.7(2) . . ?
C17 C5 C6 111.75(19) . . ?
C17 C5 H5 106.9 . . ?
C4 C5 H5 106.9 . . ?
C6 C5 C4 111.27(19) . . ?
C6 C5 H5 106.9 . . ?
O3 C16 C4 126.0(2) . . ?
O3 C16 H16 117.0 . . ?
C4 C16 H16 117.0 . . ?
C17 C22 H22 119.9 . . ?
C17 C22 C21 120.2(2) . . ?
C21 C22 H22 119.9 . . ?
C3 C7 H7 117.8 . . ?
C8 C7 C3 124.3(2) . . ?
C8 C7 H7 117.8 . . ?
C7 C8 H8 116.3 . . ?
C7 C8 C9 127.3(2) . . ?
C9 C8 H8 116.3 . . ?
O1 C1 C6 121.9(2) . . ?
O1 C1 C2 121.4(2) . . ?
C2 C1 C6 116.6(2) . . ?
C10 C9 C8 118.1(2) . . ?
C14 C9 C8 122.8(2) . . ?
C14 C9 C10 119.1(2) . . ?
C20 C21 C22 120.3(2) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1 C2 C3 112.79(19) . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 120.0 . . ?
O2 C11 C10 123.9(3) . . ?
O2 C11 C12 115.5(2) . . ?
C12 C11 C10 120.6(3) . . ?
O4 C23 H23A 109.5 . . ?
O4 C23 H23B 109.5 . . ?
O4 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C9 C14 H14 119.8 . . ?
C9 C14 C13 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.5(3) . . ?
C13 C12 H12 120.2 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C13 H13 119.8 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.8 . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.100
_oxdiff_exptl_absorpt_empirical_full_min 0.932
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate, hexane'
####################################################################### 
# 
# 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_bmstpd
_database_code_depnum_ccdc_archive 'CCDC 859678'
loop_
_audit_author_name
_audit_author_address
'Hadi Arman'
;UTSA
United States of America
;
_audit_update_record             
;
2011-12-21 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
#TrackingRef '8761_web_deposit_cif_file_0_HadiDArman_1324493775.bmstpd.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2-Benzyl-6-(2-chloro-phenyl)-4-methyl-4-styrl-tetrahydro-
pyrrolo[3,4-c]pyrrole-1,3-dione
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H25 Cl N2 O2'
_chemical_formula_sum            'C28 H25 Cl N2 O2'
_chemical_formula_weight         456.95

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2d'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   22.889(3)
_cell_length_b                   38.418(6)
_cell_length_c                   10.5749(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     9299(2)
_cell_formula_units_Z            16
_cell_measurement_temperature    98(2)
_cell_measurement_reflns_used    10626
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      40.2

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3840
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.724
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
;

;

_diffrn_ambient_temperature      98(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        <1
_diffrn_reflns_number            14341
_diffrn_reflns_av_R_equivalents  0.0894
_diffrn_reflns_av_sigmaI/netI    0.0671
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_reduction_process 'Lp corrections applied'
_reflns_number_total             4594
_reflns_number_gt                4410
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'publCIF (Westrip, 2010)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0700P)²+2.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_number_reflns         4594
_refine_ls_number_parameters     373
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.1093
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.003
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.05654(3) 0.071440(14) 0.45714(5) 0.03587(15) Uani 1 1 d . . .
N2 N -0.02637(7) 0.15893(4) 0.66360(15) 0.0177(3) Uani 1 1 d . . .
C14 C 0.02591(7) 0.10249(5) 0.67893(17) 0.0185(3) Uani 1 1 d . . .
C3 C 0.01768(7) 0.13619(5) 0.60614(17) 0.0180(3) Uani 1 1 d . . .
N1 N 0.10196(7) 0.18763(4) 0.78814(16) 0.0214(3) Uani 1 1 d . . .
C5 C 0.04798(8) 0.19770(5) 0.60166(18) 0.0194(3) Uani 1 1 d . . .
C23 C -0.05237(8) 0.22124(5) 0.67250(19) 0.0203(4) Uani 1 1 d . . .
C4 C -0.01996(8) 0.19315(5) 0.60140(16) 0.0191(3) Uani 1 1 d . . .
C1 C 0.11037(7) 0.15786(5) 0.71721(18) 0.0204(4) Uani 1 1 d . . .
C26 C -0.12753(8) 0.27682(5) 0.79348(18) 0.0232(4) Uani 1 1 d . . .
O1 O 0.14242(6) 0.13429(4) 0.74723(15) 0.0285(3) Uani 1 1 d . . .
O2 O 0.06380(6) 0.24264(4) 0.76245(16) 0.0304(3) Uani 1 1 d . . .
C6 C 0.07060(8) 0.21321(5) 0.72381(17) 0.0214(4) Uani 1 1 d . . .
C15 C 0.01795(8) 0.10128(5) 0.81005(19) 0.0228(4) Uani 1 1 d . . .
C19 C 0.04224(8) 0.07185(5) 0.61963(18) 0.0223(4) Uani 1 1 d . . .
C25 C -0.11875(7) 0.24322(5) 0.84248(17) 0.0201(4) Uani 1 1 d . . .
C27 C -0.16105(9) 0.30114(5) 0.8578(2) 0.0242(4) Uani 1 1 d . . .
C30 C -0.14440(8) 0.23540(5) 0.9590(2) 0.0237(4) Uani 1 1 d . . .
C2 C 0.07273(7) 0.16024(5) 0.59926(17) 0.0186(3) Uani 1 1 d . . .
C29 C -0.17764(8) 0.25966(6) 1.0241(2) 0.0270(4) Uani 1 1 d . . .
C28 C -0.18666(8) 0.29266(6) 0.9733(2) 0.0265(4) Uani 1 1 d . . .
C24 C -0.08432(8) 0.21632(5) 0.77605(18) 0.0200(3) Uani 1 1 d . . .
C20 C -0.04100(9) 0.19343(6) 0.4632(2) 0.0270(4) Uani 1 1 d . . .
C13 C 0.02633(9) 0.18566(6) 1.0281(2) 0.0292(4) Uani 1 1 d . . .
C18 C 0.04945(9) 0.04048(5) 0.6848(2) 0.0298(5) Uani 1 1 d . . .
C16 C 0.02595(9) 0.07048(6) 0.8776(2) 0.0277(4) Uani 1 1 d . . .
C17 C 0.04143(9) 0.04003(6) 0.8140(2) 0.0304(5) Uani 1 1 d . . .
C9 C 0.10288(10) 0.14475(6) 1.0786(2) 0.0312(4) Uani 1 1 d . . .
C8 C 0.08369(9) 0.17374(5) 1.01028(18) 0.0251(4) Uani 1 1 d . . .
C7 C 0.12380(9) 0.19196(6) 0.91783(19) 0.0275(4) Uani 1 1 d . . .
C12 C -0.01047(10) 0.16906(7) 1.1131(2) 0.0352(5) Uani 1 1 d . . .
C10 C 0.06539(13) 0.12807(7) 1.1632(2) 0.0393(5) Uani 1 1 d . . .
C11 C 0.00885(12) 0.14018(7) 1.1800(2) 0.0379(5) Uani 1 1 d . . .
H3A H 0.0065(13) 0.1291(9) 0.522(3) 0.045 Uiso 1 1 d . . .
H26A H -0.1117(13) 0.2840(9) 0.713(3) 0.045 Uiso 1 1 d . . .
H15A H 0.0082(14) 0.1234(9) 0.858(3) 0.045 Uiso 1 1 d . . .
H27A H -0.1690(14) 0.3257(9) 0.824(3) 0.045 Uiso 1 1 d . . .
H16A H 0.0173(14) 0.0717(8) 0.968(3) 0.045 Uiso 1 1 d . . .
H13A H 0.0115(13) 0.2053(9) 0.980(3) 0.045 Uiso 1 1 d . . .
H17A H 0.0475(13) 0.0199(9) 0.857(3) 0.045 Uiso 1 1 d . . .
H28A H -0.2111(13) 0.3094(8) 1.024(3) 0.045 Uiso 1 1 d . . .
H5A H 0.0590(13) 0.2127(9) 0.529(3) 0.045 Uiso 1 1 d . . .
H11A H -0.0158(14) 0.1290(9) 1.235(3) 0.045 Uiso 1 1 d . . .
H7A H 0.1653(14) 0.1813(8) 0.920(3) 0.045 Uiso 1 1 d . . .
H24A H -0.0871(14) 0.1908(9) 0.809(3) 0.045 Uiso 1 1 d . . .
H2A H 0.0947(14) 0.1549(8) 0.525(3) 0.045 Uiso 1 1 d . . .
H30A H -0.1398(13) 0.2123(9) 0.996(3) 0.045 Uiso 1 1 d . . .
H23A H -0.0486(14) 0.2449(9) 0.633(3) 0.045 Uiso 1 1 d . . .
H2B H -0.0614(15) 0.1497(9) 0.645(3) 0.045 Uiso 1 1 d . . .
H18A H 0.0614(14) 0.0187(9) 0.641(3) 0.045 Uiso 1 1 d . . .
H7B H 0.1210(13) 0.2156(9) 0.936(3) 0.045 Uiso 1 1 d . . .
H20A H -0.0828(16) 0.1858(10) 0.451(3) 0.057 Uiso 1 1 d . . .
H20B H -0.0174(16) 0.1777(10) 0.406(4) 0.057 Uiso 1 1 d . . .
H29A H -0.1951(14) 0.2535(9) 1.095(3) 0.045 Uiso 1 1 d . . .
H10A H 0.0830(13) 0.1092(8) 1.212(3) 0.045 Uiso 1 1 d . . .
H9A H 0.1418(14) 0.1375(8) 1.064(3) 0.045 Uiso 1 1 d . . .
H20C H -0.0387(15) 0.2166(10) 0.424(3) 0.057 Uiso 1 1 d . . .
H12A H -0.0490(14) 0.1759(9) 1.126(3) 0.045 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
Cl1 C19 1.749(2) . ?
N2 C3 1.466(2) . ?
N2 C4 1.478(2) . ?
N2 H2B 0.90(3) . ?
C14 C19 1.385(3) . ?
C14 C15 1.399(3) . ?
C14 C3 1.518(2) . ?
C3 C2 1.564(2) . ?
C3 H3A 0.97(3) . ?
N1 C1 1.381(2) . ?
N1 C6 1.394(2) . ?
N1 C7 1.469(2) . ?
C5 C6 1.514(3) . ?
C5 C2 1.547(3) . ?
C5 C4 1.565(2) . ?
C5 H5A 0.99(4) . ?
C23 C24 1.330(3) . ?
C23 C4 1.510(3) . ?
C23 H23A 1.01(3) . ?
C4 C20 1.539(3) . ?
C1 O1 1.208(2) . ?
C1 C2 1.519(2) . ?
C26 C27 1.387(3) . ?
C26 C25 1.406(3) . ?
C26 H26A 0.97(3) . ?
O2 C6 1.212(2) . ?
C15 C16 1.394(3) . ?
C15 H15A 1.01(3) . ?
C19 C18 1.398(3) . ?
C25 C30 1.398(3) . ?
C25 C24 1.477(3) . ?
C27 C28 1.393(3) . ?
C27 H27A 1.03(3) . ?
C30 C29 1.386(3) . ?
C30 H30A 0.98(3) . ?
C2 H2A 0.96(3) . ?
C29 C28 1.392(3) . ?
C29 H29A 0.88(3) . ?
C28 H28A 1.01(3) . ?
C24 H24A 1.05(3) . ?
C20 H20A 1.01(4) . ?
C20 H20B 1.01(4) . ?
C20 H20C 0.98(4) . ?
C13 C12 1.387(3) . ?
C13 C8 1.403(3) . ?
C13 H13A 0.97(3) . ?
C18 C17 1.379(4) . ?
C18 H18A 1.00(3) . ?
C16 C17 1.395(3) . ?
C16 H16A 0.98(3) . ?
C17 H17A 0.91(3) . ?
C9 C10 1.396(4) . ?
C9 C8 1.398(3) . ?
C9 H9A 0.95(3) . ?
C8 C7 1.513(3) . ?
C7 H7A 1.03(3) . ?
C7 H7B 0.93(3) . ?
C12 C11 1.388(4) . ?
C12 H12A 0.93(3) . ?
C10 C11 1.387(4) . ?
C10 H10A 0.98(3) . ?
C11 H11A 0.92(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N2 C4 106.11(13) . . ?
C3 N2 H2B 107(2) . . ?
C4 N2 H2B 110(2) . . ?
C19 C14 C15 117.09(18) . . ?
C19 C14 C3 121.92(16) . . ?
C15 C14 C3 120.99(17) . . ?
N2 C3 C14 112.54(14) . . ?
N2 C3 C2 102.79(14) . . ?
C14 C3 C2 115.30(15) . . ?
N2 C3 H3A 111.7(19) . . ?
C14 C3 H3A 105(2) . . ?
C2 C3 H3A 109.7(19) . . ?
C1 N1 C6 112.99(16) . . ?
C1 N1 C7 123.59(17) . . ?
C6 N1 C7 123.41(17) . . ?
C6 C5 C2 104.78(15) . . ?
C6 C5 C4 112.66(15) . . ?
C2 C5 C4 105.07(14) . . ?
C6 C5 H5A 110.1(18) . . ?
C2 C5 H5A 115.8(19) . . ?
C4 C5 H5A 108.4(17) . . ?
C24 C23 C4 125.36(17) . . ?
C24 C23 H23A 121.4(19) . . ?
C4 C23 H23A 113.2(19) . . ?
N2 C4 C23 111.43(15) . . ?
N2 C4 C20 113.44(16) . . ?
C23 C4 C20 108.31(15) . . ?
N2 C4 C5 101.37(13) . . ?
C23 C4 C5 114.06(15) . . ?
C20 C4 C5 108.18(15) . . ?
O1 C1 N1 124.25(18) . . ?
O1 C1 C2 127.27(18) . . ?
N1 C1 C2 108.48(15) . . ?
C27 C26 C25 121.12(18) . . ?
C27 C26 H26A 116.7(19) . . ?
C25 C26 H26A 122.2(19) . . ?
O2 C6 N1 124.00(18) . . ?
O2 C6 C5 127.66(18) . . ?
N1 C6 C5 108.35(15) . . ?
C16 C15 C14 121.28(19) . . ?
C16 C15 H15A 119.0(18) . . ?
C14 C15 H15A 119.6(18) . . ?
C14 C19 C18 122.78(18) . . ?
C14 C19 Cl1 120.19(15) . . ?
C18 C19 Cl1 117.01(16) . . ?
C30 C25 C26 117.54(17) . . ?
C30 C25 C24 119.54(17) . . ?
C26 C25 C24 122.92(17) . . ?
C26 C27 C28 120.36(19) . . ?
C26 C27 H27A 123.0(19) . . ?
C28 C27 H27A 116.6(19) . . ?
C29 C30 C25 121.57(19) . . ?
C29 C30 H30A 118.1(19) . . ?
C25 C30 H30A 120.3(19) . . ?
C1 C2 C5 104.49(15) . . ?
C1 C2 C3 112.54(14) . . ?
C5 C2 C3 104.71(14) . . ?
C1 C2 H2A 111.5(19) . . ?
C5 C2 H2A 113.8(19) . . ?
C3 C2 H2A 109.6(19) . . ?
C30 C29 C28 120.17(19) . . ?
C30 C29 H29A 119(2) . . ?
C28 C29 H29A 120(2) . . ?
C29 C28 C27 119.23(18) . . ?
C29 C28 H28A 117.4(19) . . ?
C27 C28 H28A 123.4(19) . . ?
C23 C24 C25 125.84(17) . . ?
C23 C24 H24A 116.4(18) . . ?
C25 C24 H24A 117.7(18) . . ?
C4 C20 H20A 114(2) . . ?
C4 C20 H20B 113(2) . . ?
H20A C20 H20B 105(3) . . ?
C4 C20 H20C 113(2) . . ?
H20A C20 H20C 105(3) . . ?
H20B C20 H20C 105(3) . . ?
C12 C13 C8 120.3(2) . . ?
C12 C13 H13A 119.0(18) . . ?
C8 C13 H13A 120.6(18) . . ?
C17 C18 C19 118.9(2) . . ?
C17 C18 H18A 119(2) . . ?
C19 C18 H18A 122(2) . . ?
C15 C16 C17 119.8(2) . . ?
C15 C16 H16A 115.7(19) . . ?
C17 C16 H16A 124.3(19) . . ?
C18 C17 C16 120.11(19) . . ?
C18 C17 H17A 119(2) . . ?
C16 C17 H17A 121(2) . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 H9A 123(2) . . ?
C8 C9 H9A 117(2) . . ?
C9 C8 C13 119.0(2) . . ?
C9 C8 C7 120.79(19) . . ?
C13 C8 C7 120.23(19) . . ?
N1 C7 C8 110.14(16) . . ?
N1 C7 H7A 106.7(18) . . ?
C8 C7 H7A 111.1(18) . . ?
N1 C7 H7B 106.0(19) . . ?
C8 C7 H7B 106.2(19) . . ?
H7A C7 H7B 117(3) . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12A 123(2) . . ?
C11 C12 H12A 117(2) . . ?
C11 C10 C9 120.1(2) . . ?
C11 C10 H10A 124.6(18) . . ?
C9 C10 H10A 115.1(18) . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11A 120(2) . . ?
C12 C11 H11A 120(2) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.049


####################################################################### 
# 
# 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_hpd122
_database_code_depnum_ccdc_archive 'CCDC 2043408'
loop_
_audit_author_name
_audit_author_address
'Hadi Arman'
;UTSA
United States of America
;
_audit_update_record             
;
2020-11-09 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
_audit_creation_date             2020-06-17
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
(1R,2R,6S)-2-(4-nitrophenyl)-6-[(E)-4-nitrostyryl]-4-oxocyclohexane-1-carbaldehyde
_chemical_formula_moiety         'C21 H18 N2 O6'
_chemical_formula_sum            'C21 H18 N2 O6'
_chemical_formula_weight         394.37
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     Pure1-RP-2120
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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   21.5200(4)
_cell_length_b                   5.22340(10)
_cell_length_c                   16.8010(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.046(2)
_cell_angle_gamma                90
_cell_volume                     1885.89(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7833
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.3200
_cell_measurement_theta_min      2.6290
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.849
_exptl_absorpt_coefficient_mu    0.863
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.637
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             824
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -3 -6 0.0909
14 0 -1 0.0296
0 3 6 0.0498
-14 0 0 0.0193
-7 -2 6 0.0943
-9 0 -8 0.0280
5 2 -7 0.0661
9 0 8 0.0146

_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.046
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.1921 -2.8962 -5.6595 -0.6151 -0.5236 0.5895
13.9512 0.1389 -0.8848 -0.4263 -0.3659 -0.8273
-0.3795 2.8921 5.6988 0.6329 0.5389 -0.5559
-13.8561 -0.4226 0.3210 0.3624 0.3114 0.8785
-6.8114 -2.4655 5.5442 0.4990 -0.5829 0.6412
-9.4491 -0.3138 -7.5637 -0.3931 0.4627 0.7946
5.0047 2.3851 -6.8902 -0.5670 0.6631 -0.4887
9.1086 0.1877 7.8549 0.4190 -0.4930 -0.7624

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13035
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.432
_diffrn_reflns_theta_min         2.634
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  72.00   0.50    2.80    --   46.75 -80.00  15.00  194
  2  ω     34.00 132.00   0.50   11.20    --  106.69 -80.00  15.00  196
  3  ω     92.00 178.00   0.50   11.20    --  106.69  45.00  90.00  172
  4  ω     83.00 119.00   0.50    2.80    --   46.75  57.00  60.00   72
  5  ω     82.00 178.00   0.50   11.20    --  106.69  80.00 139.00  192
  6  ω     34.00 101.00   0.50   11.20    --  106.69 -77.00 -90.00  134
  7  ω     34.00 101.00   0.50   11.20    --  106.69 -77.00-150.00  134
  8  ω     34.00 111.00   0.50   11.20    --  106.69-125.00-120.00  154
  9  ω     34.00  71.00   0.50   11.20    --  106.69 -61.00  90.00   74
 10  ω     34.00  71.00   0.50   11.20    --  106.69 -61.00 150.00   74
 11  ω     22.00 119.00   0.50    2.80    --   46.75  80.00 139.00  194
 12  ω    -51.00 -16.00   0.50   11.20    --  -88.50  45.00 -30.00   70
 13  ω    -51.00 -16.00   0.50   11.20    --  -88.50  45.00 -90.00   70
 14  ω   -119.00 -21.00   0.50    2.80    --  -46.75 -80.00  15.00  196
 15  ω    -72.00  26.00   0.50    2.80    --  -46.75  80.00 139.00  196
 16  ω   -114.00 -15.00   0.50   11.20    --  -88.50  80.00 139.00  198
 17  ω   -119.00 -83.00   0.50    2.80    --  -46.75 -57.00 -60.00   72
 18  ω   -119.00 -87.00   0.50    2.80    --  -46.75-125.00  60.00   64
 19  ω   -119.00 -87.00   0.50    2.80    --  -46.75-125.00  90.00   64
 20  ω   -160.00 -91.00   0.50   11.20    --  -88.50 -61.00  30.00  138
 21  ω   -160.00 -91.00   0.50   11.20    --  -88.50 -61.00 -90.00  138
 22  ω   -160.00 -63.00   0.50   11.20    --  -88.50 -80.00  15.00  194
 23  ω   -161.00 -74.00   0.50   11.20    --  -88.50 -45.00  60.00  174
 24  ω   -163.00 -73.00   0.50   11.20    --  -88.50 -30.00  90.00  180
 25  ω   -161.00 -74.00   0.50   11.20    --  -88.50 -45.00 -60.00  174
 26  ω   -163.00 -73.00   0.50   11.20    --  -88.50 -30.00-120.00  180
 27  ω   -161.00 -74.00   0.50   11.20    --  -88.50 -45.00-150.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0258884000
_diffrn_orient_matrix_UB_12      0.0537048000
_diffrn_orient_matrix_UB_13      0.0820845000
_diffrn_orient_matrix_UB_21      -0.0307778000
_diffrn_orient_matrix_UB_22      0.2472844000
_diffrn_orient_matrix_UB_23      -0.0329871000
_diffrn_orient_matrix_UB_31      -0.0593514000
_diffrn_orient_matrix_UB_32      -0.1514802000
_diffrn_orient_matrix_UB_33      -0.0246216000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_full    0.956
_reflns_Friedel_fraction_max     0.840
_reflns_number_gt                3391
_reflns_number_total             3580
_reflns_odcompleteness_completeness 99.95
_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 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 
;
 Flack x determined using 1314 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3580
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0553
_refine_ls_restrained_S_all      1.081
_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)+(0.0550P)²+4.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1343
_refine_ls_wR_factor_ref         0.1373
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C1(H1), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C17(H17), C8(H8), C12(H12), C14(H14), C20(H20), C18(H18), C9(H9),
 C15(H15), C11(H11), C21(H21)
;
_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
O5 O 0.67471(13) 0.2467(7) 0.38205(17) 0.0385(7) Uani 1 1 d . . . . .
O3 O 0.20057(13) 1.2140(6) 0.77490(17) 0.0369(7) Uani 1 1 d . . . . .
O4 O 0.21108(15) 1.2678(7) 0.90162(18) 0.0421(8) Uani 1 1 d . . . . .
O1 O 0.44442(14) -0.2687(6) 0.63639(19) 0.0402(8) Uani 1 1 d . . . . .
O6 O 0.72817(14) -0.0547(7) 0.44014(18) 0.0386(7) Uani 1 1 d . . . . .
O2 O 0.56814(14) 0.4023(6) 0.92492(17) 0.0398(8) Uani 1 1 d . . . . .
N1 N 0.22301(14) 1.1563(7) 0.84091(19) 0.0284(8) Uani 1 1 d . . . . .
N2 N 0.68657(15) 0.1080(7) 0.43864(19) 0.0288(8) Uani 1 1 d . . . . .
C4 C 0.55843(17) 0.2499(8) 0.8717(2) 0.0274(8) Uani 1 1 d . . . . .
C7 C 0.46227(17) -0.0622(8) 0.6584(2) 0.0267(8) Uani 1 1 d . . . . .
H7 H 0.447874 0.083460 0.628978 0.032 Uiso 1 1 calc R U . . .
C17 C 0.57449(18) 0.3624(8) 0.5807(2) 0.0261(8) Uani 1 1 d . . . . .
H17 H 0.544895 0.496681 0.583371 0.031 Uiso 1 1 calc R U . . .
C16 C 0.58300(16) 0.1962(8) 0.6445(2) 0.0240(8) Uani 1 1 d . . . . .
C6 C 0.54647(16) 0.2199(7) 0.7190(2) 0.0233(8) Uani 1 1 d . . . . .
H6 H 0.517863 0.370061 0.711963 0.028 Uiso 1 1 calc R U . . .
C1 C 0.50653(17) -0.0198(7) 0.7304(2) 0.0236(8) Uani 1 1 d . . . . .
H1 H 0.534963 -0.171001 0.735681 0.028 Uiso 1 1 calc R U . . .
C8 C 0.42057(17) 0.2056(8) 0.8018(2) 0.0262(8) Uani 1 1 d . . . . .
H8 H 0.398409 0.226394 0.751780 0.031 Uiso 1 1 calc R U . . .
C12 C 0.29687(18) 0.8859(8) 0.9185(2) 0.0287(9) Uani 1 1 d . . . . .
H12 H 0.286542 0.975463 0.965238 0.034 Uiso 1 1 calc R U . . .
C19 C 0.65088(16) 0.1384(8) 0.5107(2) 0.0253(8) Uani 1 1 d . . . . .
C14 C 0.28079(18) 0.8170(8) 0.7765(2) 0.0296(9) Uani 1 1 d . . . . .
H14 H 0.259648 0.860559 0.727332 0.035 Uiso 1 1 calc R U . . .
C10 C 0.35580(18) 0.5583(8) 0.8537(2) 0.0262(8) Uani 1 1 d . . . . .
C13 C 0.26857(17) 0.9450(8) 0.8457(2) 0.0264(8) Uani 1 1 d . . . . .
C20 C 0.66031(18) -0.0326(9) 0.5717(2) 0.0301(9) Uani 1 1 d . . . . .
H20 H 0.689323 -0.168606 0.567980 0.036 Uiso 1 1 calc R U . . .
C18 C 0.60839(18) 0.3374(8) 0.5126(2) 0.0270(8) Uani 1 1 d . . . . .
H18 H 0.602550 0.452637 0.469116 0.032 Uiso 1 1 calc R U . . .
C9 C 0.40564(18) 0.3617(8) 0.8596(2) 0.0266(8) Uani 1 1 d . . . . .
H9 H 0.428775 0.346903 0.909112 0.032 Uiso 1 1 calc R U . . .
C15 C 0.32500(18) 0.6223(9) 0.7808(2) 0.0301(9) Uani 1 1 d . . . . .
H15 H 0.334373 0.531846 0.733866 0.036 Uiso 1 1 calc R U . . .
C11 C 0.34119(18) 0.6909(8) 0.9221(2) 0.0280(8) Uani 1 1 d . . . . .
H11 H 0.361657 0.648124 0.971802 0.034 Uiso 1 1 calc R U . . .
C2 C 0.46931(18) -0.0026(7) 0.8072(2) 0.0258(8) Uani 1 1 d . . . . .
H2 H 0.447028 -0.169169 0.812665 0.031 Uiso 1 1 calc R U . . .
C5 C 0.58986(18) 0.2686(9) 0.7937(2) 0.0295(9) Uani 1 1 d . . . . .
H5A H 0.624363 0.143114 0.794214 0.035 Uiso 1 1 calc R U . . .
H5B H 0.608252 0.441471 0.789512 0.035 Uiso 1 1 calc R U . . .
C21 C 0.62651(18) -0.0028(8) 0.6391(2) 0.0309(9) Uani 1 1 d . . . . .
H21 H 0.632876 -0.118810 0.682313 0.037 Uiso 1 1 calc R U . . .
C3 C 0.5157(2) 0.0229(8) 0.8794(2) 0.0308(9) Uani 1 1 d . . . . .
H3A H 0.492484 0.041858 0.928399 0.037 Uiso 1 1 calc R U . . .
H3B H 0.540972 -0.135233 0.884764 0.037 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
O5 N2 1.212(4) . ?
O3 N1 1.223(4) . ?
O4 N1 1.214(5) . ?
O1 C7 1.196(5) . ?
O6 N2 1.234(5) . ?
O2 C4 1.207(5) . ?
N1 C13 1.476(5) . ?
N2 C19 1.477(5) . ?
C4 C5 1.511(5) . ?
C4 C3 1.510(6) . ?
C7 H7 0.9500 . ?
C7 C1 1.516(5) . ?
C17 H17 0.9500 . ?
C17 C16 1.384(5) . ?
C17 C18 1.395(5) . ?
C16 C6 1.518(5) . ?
C16 C21 1.405(5) . ?
C6 H6 1.0000 . ?
C6 C1 1.537(5) . ?
C6 C5 1.545(5) . ?
C1 H1 1.0000 . ?
C1 C2 1.557(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.320(6) . ?
C8 C2 1.511(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.373(5) . ?
C12 C11 1.394(6) . ?
C19 C20 1.366(6) . ?
C19 C18 1.386(5) . ?
C14 H14 0.9500 . ?
C14 C13 1.378(6) . ?
C14 C15 1.392(6) . ?
C10 C9 1.484(5) . ?
C10 C15 1.402(6) . ?
C10 C11 1.392(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.387(5) . ?
C18 H18 0.9500 . ?
C9 H9 0.9500 . ?
C15 H15 0.9500 . ?
C11 H11 0.9500 . ?
C2 H2 1.0000 . ?
C2 C3 1.537(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C21 H21 0.9500 . ?
C3 H3A 0.9900 . ?
C3 H3B 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
O3 N1 C13 117.6(3) . . ?
O4 N1 O3 123.6(4) . . ?
O4 N1 C13 118.8(3) . . ?
O5 N2 O6 123.4(3) . . ?
O5 N2 C19 118.8(3) . . ?
O6 N2 C19 117.8(3) . . ?
O2 C4 C5 122.2(4) . . ?
O2 C4 C3 122.5(4) . . ?
C3 C4 C5 115.3(3) . . ?
O1 C7 H7 118.1 . . ?
O1 C7 C1 123.8(4) . . ?
C1 C7 H7 118.1 . . ?
C16 C17 H17 119.2 . . ?
C16 C17 C18 121.5(4) . . ?
C18 C17 H17 119.2 . . ?
C17 C16 C6 122.3(3) . . ?
C17 C16 C21 118.4(3) . . ?
C21 C16 C6 119.3(3) . . ?
C16 C6 H6 108.0 . . ?
C16 C6 C1 110.7(3) . . ?
C16 C6 C5 111.5(3) . . ?
C1 C6 H6 108.0 . . ?
C1 C6 C5 110.6(3) . . ?
C5 C6 H6 108.0 . . ?
C7 C1 C6 110.6(3) . . ?
C7 C1 H1 108.1 . . ?
C7 C1 C2 109.9(3) . . ?
C6 C1 H1 108.1 . . ?
C6 C1 C2 111.8(3) . . ?
C2 C1 H1 108.1 . . ?
C9 C8 H8 116.7 . . ?
C9 C8 C2 126.6(4) . . ?
C2 C8 H8 116.7 . . ?
C13 C12 H12 120.9 . . ?
C13 C12 C11 118.2(4) . . ?
C11 C12 H12 120.9 . . ?
C20 C19 N2 118.8(3) . . ?
C20 C19 C18 123.0(4) . . ?
C18 C19 N2 118.2(3) . . ?
C13 C14 H14 120.9 . . ?
C13 C14 C15 118.1(4) . . ?
C15 C14 H14 120.9 . . ?
C15 C10 C9 122.0(4) . . ?
C11 C10 C9 118.9(3) . . ?
C11 C10 C15 119.0(4) . . ?
C12 C13 N1 118.6(4) . . ?
C12 C13 C14 123.2(4) . . ?
C14 C13 N1 118.2(3) . . ?
C19 C20 H20 120.8 . . ?
C19 C20 C21 118.4(4) . . ?
C21 C20 H20 120.8 . . ?
C17 C18 H18 121.2 . . ?
C19 C18 C17 117.6(4) . . ?
C19 C18 H18 121.2 . . ?
C8 C9 C10 125.6(4) . . ?
C8 C9 H9 117.2 . . ?
C10 C9 H9 117.2 . . ?
C14 C15 C10 120.6(4) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C12 C11 H11 119.6 . . ?
C10 C11 C12 120.8(4) . . ?
C10 C11 H11 119.6 . . ?
C1 C2 H2 107.3 . . ?
C8 C2 C1 112.2(3) . . ?
C8 C2 H2 107.3 . . ?
C8 C2 C3 113.9(3) . . ?
C3 C2 C1 108.6(3) . . ?
C3 C2 H2 107.3 . . ?
C4 C5 C6 114.5(3) . . ?
C4 C5 H5A 108.6 . . ?
C4 C5 H5B 108.6 . . ?
C6 C5 H5A 108.6 . . ?
C6 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
C16 C21 H21 119.5 . . ?
C20 C21 C16 121.1(4) . . ?
C20 C21 H21 119.5 . . ?
C4 C3 C2 111.9(3) . . ?
C4 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?

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
O5 N2 C19 C20 174.2(4) . . . . ?
O5 N2 C19 C18 -4.7(5) . . . . ?
O3 N1 C13 C12 176.5(4) . . . . ?
O3 N1 C13 C14 -3.2(5) . . . . ?
O4 N1 C13 C12 -1.5(6) . . . . ?
O4 N1 C13 C14 178.8(4) . . . . ?
O1 C7 C1 C6 149.9(4) . . . . ?
O1 C7 C1 C2 -86.1(5) . . . . ?
O6 N2 C19 C20 -7.5(5) . . . . ?
O6 N2 C19 C18 173.6(4) . . . . ?
O2 C4 C5 C6 -136.9(4) . . . . ?
O2 C4 C3 C2 131.8(4) . . . . ?
N2 C19 C20 C21 -179.9(4) . . . . ?
N2 C19 C18 C17 179.3(3) . . . . ?
C7 C1 C2 C8 -56.8(4) . . . . ?
C7 C1 C2 C3 176.4(3) . . . . ?
C17 C16 C6 C1 117.7(4) . . . . ?
C17 C16 C6 C5 -118.9(4) . . . . ?
C17 C16 C21 C20 0.1(6) . . . . ?
C16 C17 C18 C19 0.4(6) . . . . ?
C16 C6 C1 C7 -58.1(4) . . . . ?
C16 C6 C1 C2 179.1(3) . . . . ?
C16 C6 C5 C4 -170.1(4) . . . . ?
C6 C16 C21 C20 179.3(4) . . . . ?
C6 C1 C2 C8 66.4(4) . . . . ?
C6 C1 C2 C3 -60.4(4) . . . . ?
C1 C6 C5 C4 -46.6(5) . . . . ?
C1 C2 C3 C4 56.4(4) . . . . ?
C8 C2 C3 C4 -69.4(4) . . . . ?
C19 C20 C21 C16 0.8(6) . . . . ?
C13 C12 C11 C10 -0.6(6) . . . . ?
C13 C14 C15 C10 0.3(6) . . . . ?
C20 C19 C18 C17 0.5(6) . . . . ?
C18 C17 C16 C6 -179.9(4) . . . . ?
C18 C17 C16 C21 -0.7(6) . . . . ?
C18 C19 C20 C21 -1.1(6) . . . . ?
C9 C8 C2 C1 -140.7(4) . . . . ?
C9 C8 C2 C3 -16.9(6) . . . . ?
C9 C10 C15 C14 -176.5(4) . . . . ?
C9 C10 C11 C12 176.8(4) . . . . ?
C15 C14 C13 N1 178.3(4) . . . . ?
C15 C14 C13 C12 -1.4(6) . . . . ?
C15 C10 C9 C8 -9.4(6) . . . . ?
C15 C10 C11 C12 -0.4(6) . . . . ?
C11 C12 C13 N1 -178.1(3) . . . . ?
C11 C12 C13 C14 1.6(6) . . . . ?
C11 C10 C9 C8 173.5(4) . . . . ?
C11 C10 C15 C14 0.5(6) . . . . ?
C2 C8 C9 C10 -177.4(4) . . . . ?
C5 C4 C3 C2 -50.1(5) . . . . ?
C5 C6 C1 C7 177.9(3) . . . . ?
C5 C6 C1 C2 55.1(4) . . . . ?
C21 C16 C6 C1 -61.5(4) . . . . ?
C21 C16 C6 C5 62.0(5) . . . . ?
C3 C4 C5 C6 45.0(5) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.889
_oxdiff_exptl_absorpt_empirical_full_min 0.563
