# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_189-1
_database_code_depnum_ccdc_archive 'CCDC 2167329'
loop_
_audit_author_name
_audit_author_address
lifuyu
;cdyjs
China
;
_audit_update_record             
;
2022-04-19 deposited with the CCDC.	2023-02-10 downloaded from the CCDC.
;
_audit_creation_date             2021-03-29
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H20 O2'
_chemical_formula_sum            'C17 H20 O2'
_chemical_formula_weight         256.33
_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 0.0033 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                   10.8532(7)
_cell_length_b                   15.9018(9)
_cell_length_c                   8.3007(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.936(7)
_cell_angle_gamma                90
_cell_volume                     1355.05(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2630
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      28.6550
_cell_measurement_theta_min      2.3700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.256
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5432
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.984
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00  42.00   1.00    1.20    --   12.05 -77.00 -30.00   96
  2  ω     -2.00  81.00   1.00    1.20    --   12.05  57.00  90.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0073139000
_diffrn_orient_matrix_UB_12      -0.0442653000
_diffrn_orient_matrix_UB_13      0.0030521000
_diffrn_orient_matrix_UB_21      0.0109716000
_diffrn_orient_matrix_UB_22      0.0024024000
_diffrn_orient_matrix_UB_23      0.0888536000
_diffrn_orient_matrix_UB_31      -0.0678246000
_diffrn_orient_matrix_UB_32      0.0051218000
_diffrn_orient_matrix_UB_33      -0.0158276000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2028
_reflns_number_total             2378
_reflns_odcompleteness_completeness 99.97
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2378
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.079
_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)+(0.0405P)²+0.3514P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0977
_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 Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B),
 C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
;
_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 0.56634(11) 0.35487(7) 0.23285(14) 0.0365(3) Uani 1 1 d . . . . .
O2 O 0.72124(10) 0.35944(7) 0.48119(13) 0.0287(3) Uani 1 1 d . . . . .
C1 C 0.28436(14) 0.35101(9) 0.61588(17) 0.0214(3) Uani 1 1 d . . . . .
C2 C 0.18461(14) 0.40743(10) 0.61058(18) 0.0250(3) Uani 1 1 d . . . . .
H2 H 0.205483 0.460733 0.657638 0.030 Uiso 1 1 calc R U . . .
C3 C 0.05542(14) 0.38539(10) 0.5366(2) 0.0287(4) Uani 1 1 d . . . . .
H3 H -0.009662 0.423774 0.534847 0.034 Uiso 1 1 calc R U . . .
C4 C 0.02229(15) 0.30685(10) 0.4653(2) 0.0325(4) Uani 1 1 d . . . . .
H4 H -0.064730 0.292284 0.414563 0.039 Uiso 1 1 calc R U . . .
C5 C 0.11976(15) 0.24996(10) 0.4701(2) 0.0327(4) Uani 1 1 d . . . . .
H5 H 0.098043 0.196972 0.421795 0.039 Uiso 1 1 calc R U . . .
C6 C 0.24933(14) 0.27123(9) 0.54609(19) 0.0263(4) Uani 1 1 d . . . . .
H6 H 0.313804 0.231898 0.550719 0.032 Uiso 1 1 calc R U . . .
C7 C 0.42124(13) 0.37703(9) 0.69604(18) 0.0217(3) Uani 1 1 d . . . . .
H7 H 0.439499 0.407287 0.796965 0.026 Uiso 1 1 calc R U . . .
C8 C 0.52182(13) 0.36234(8) 0.64111(17) 0.0190(3) Uani 1 1 d . . . . .
C9 C 0.50654(14) 0.31605(9) 0.47649(18) 0.0223(3) Uani 1 1 d . . . . .
H9A H 0.521467 0.256593 0.501290 0.027 Uiso 1 1 calc R U . . .
H9B H 0.417494 0.322551 0.401677 0.027 Uiso 1 1 calc R U . . .
C10 C 0.59663(15) 0.34543(9) 0.38472(19) 0.0243(3) Uani 1 1 d . . . . .
C11 C 0.75132(14) 0.34603(10) 0.66254(19) 0.0255(4) Uani 1 1 d . . . . .
H11A H 0.840229 0.363603 0.721033 0.031 Uiso 1 1 calc R U . . .
H11B H 0.744924 0.286504 0.684104 0.031 Uiso 1 1 calc R U . . .
C12 C 0.65924(13) 0.39483(9) 0.73356(17) 0.0194(3) Uani 1 1 d . . . . .
C13 C 0.66509(14) 0.49013(9) 0.70043(18) 0.0223(3) Uani 1 1 d . . . . .
H13A H 0.648615 0.499085 0.579658 0.027 Uiso 1 1 calc R U . . .
H13B H 0.596428 0.518093 0.731093 0.027 Uiso 1 1 calc R U . . .
C14 C 0.79524(15) 0.53020(9) 0.79941(19) 0.0268(4) Uani 1 1 d . . . . .
H14A H 0.863517 0.506694 0.761307 0.032 Uiso 1 1 calc R U . . .
H14B H 0.791411 0.590263 0.777925 0.032 Uiso 1 1 calc R U . . .
C15 C 0.82669(15) 0.51432(10) 0.98939(19) 0.0290(4) Uani 1 1 d . . . . .
H15A H 0.910944 0.538585 1.050392 0.035 Uiso 1 1 calc R U . . .
H15B H 0.761911 0.541752 1.028789 0.035 Uiso 1 1 calc R U . . .
C16 C 0.82886(15) 0.42083(10) 1.02827(19) 0.0275(4) Uani 1 1 d . . . . .
H16A H 0.843964 0.412938 1.149039 0.033 Uiso 1 1 calc R U . . .
H16B H 0.899979 0.394413 1.000492 0.033 Uiso 1 1 calc R U . . .
C17 C 0.70072(14) 0.37877(9) 0.92678(18) 0.0240(3) Uani 1 1 d . . . . .
H17A H 0.632534 0.398950 0.968906 0.029 Uiso 1 1 calc R U . . .
H17B H 0.708918 0.318615 0.946754 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 C10 1.2045(18) . ?
O2 C10 1.3479(18) . ?
O2 C11 1.4488(18) . ?
C1 C2 1.396(2) . ?
C1 C6 1.395(2) . ?
C1 C7 1.476(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.333(2) . ?
C8 C9 1.5131(19) . ?
C8 C12 1.5289(19) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.496(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.527(2) . ?
C12 C13 1.5451(19) . ?
C12 C17 1.5400(19) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.524(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.522(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.520(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.527(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

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 O2 C11 115.93(11) . . ?
C2 C1 C7 119.40(13) . . ?
C6 C1 C2 117.86(13) . . ?
C6 C1 C7 122.73(13) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.08(14) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.42(15) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.33(14) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.54(15) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.75(14) . . ?
C5 C6 H6 119.6 . . ?
C1 C7 H7 116.1 . . ?
C8 C7 C1 127.79(13) . . ?
C8 C7 H7 116.1 . . ?
C7 C8 C9 122.16(13) . . ?
C7 C8 C12 122.88(13) . . ?
C9 C8 C12 114.89(12) . . ?
C8 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 C8 114.19(12) . . ?
C10 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
O1 C10 O2 118.80(14) . . ?
O1 C10 C9 124.77(14) . . ?
O2 C10 C9 116.40(12) . . ?
O2 C11 H11A 109.3 . . ?
O2 C11 H11B 109.3 . . ?
O2 C11 C12 111.80(11) . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C8 C12 C13 109.38(11) . . ?
C8 C12 C17 112.00(11) . . ?
C11 C12 C8 106.77(11) . . ?
C11 C12 C13 111.10(12) . . ?
C11 C12 C17 108.12(12) . . ?
C17 C12 C13 109.45(11) . . ?
C12 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 C12 113.48(11) . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C13 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 C13 110.24(12) . . ?
C15 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C14 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 C14 111.41(12) . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C15 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
C15 C16 C17 111.27(12) . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C12 C17 H17A 108.7 . . ?
C12 C17 H17B 108.7 . . ?
C16 C17 C12 114.09(12) . . ?
C16 C17 H17A 108.7 . . ?
C16 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?

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
O2 C11 C12 C8 60.84(15) . . . . ?
O2 C11 C12 C13 -58.35(15) . . . . ?
O2 C11 C12 C17 -178.48(11) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C1 C7 C8 C9 1.7(2) . . . . ?
C1 C7 C8 C12 178.29(13) . . . . ?
C2 C1 C6 C5 1.7(2) . . . . ?
C2 C1 C7 C8 -138.28(16) . . . . ?
C2 C3 C4 C5 0.6(2) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C4 C5 C6 C1 -1.5(2) . . . . ?
C6 C1 C2 C3 -0.9(2) . . . . ?
C6 C1 C7 C8 42.6(2) . . . . ?
C7 C1 C2 C3 179.96(13) . . . . ?
C7 C1 C6 C5 -179.10(14) . . . . ?
C7 C8 C9 C10 146.56(14) . . . . ?
C7 C8 C12 C11 164.74(13) . . . . ?
C7 C8 C12 C13 -74.96(17) . . . . ?
C7 C8 C12 C17 46.56(19) . . . . ?
C8 C9 C10 O1 -138.78(15) . . . . ?
C8 C9 C10 O2 43.38(18) . . . . ?
C8 C12 C13 C14 175.14(12) . . . . ?
C8 C12 C17 C16 -171.77(12) . . . . ?
C9 C8 C12 C11 -18.47(16) . . . . ?
C9 C8 C12 C13 101.84(14) . . . . ?
C9 C8 C12 C17 -136.64(12) . . . . ?
C10 O2 C11 C12 -52.76(16) . . . . ?
C11 O2 C10 O1 -179.34(13) . . . . ?
C11 O2 C10 C9 -1.36(18) . . . . ?
C11 C12 C13 C14 -67.24(15) . . . . ?
C11 C12 C17 C16 70.86(16) . . . . ?
C12 C8 C9 C10 -30.26(17) . . . . ?
C12 C13 C14 C15 -56.37(17) . . . . ?
C13 C12 C17 C16 -50.29(16) . . . . ?
C13 C14 C15 C16 57.21(17) . . . . ?
C14 C15 C16 C17 -55.67(17) . . . . ?
C15 C16 C17 C12 53.12(18) . . . . ?
C17 C12 C13 C14 52.09(16) . . . . ?

_olex2_date_sample_data_collection 2021-03-29
_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 1.196
_oxdiff_exptl_absorpt_empirical_full_min 0.709
####################################################################### 
# 
# 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_ys-5
_database_code_depnum_ccdc_archive 'CCDC 2167332'
loop_
_audit_author_name
_audit_author_address
LFYzznhz
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-04-19 deposited with the CCDC.	2023-02-10 downloaded from the CCDC.
;
_audit_creation_date             2021-10-13
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 N2 O2'
_chemical_formula_sum            'C14 H14 N2 O2'
_chemical_formula_weight         242.27
_chemical_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.4356(3)
_cell_length_b                   12.2960(5)
_cell_length_c                   15.5108(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1227.40(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1494
_cell_measurement_temperature    179.99(10)
_cell_measurement_theta_max      73.5420
_cell_measurement_theta_min      4.5600
_shelx_estimated_absorpt_T_max   0.944
_shelx_estimated_absorpt_T_min   0.905
_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3039
_diffrn_reflns_point_group_measured_fraction_full 0.913
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.820
_diffrn_reflns_theta_min         4.589
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      179.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -7.00  34.00   1.00    2.00    --  -41.11   0.00 120.00   41
  2  ω     50.00  80.00   1.00    2.00    --   41.11-125.00 -90.00   30
  3  ω     41.00 139.00   1.00    4.00    --  107.58 -77.00 -60.00   98
  4  ω     90.00 116.00   1.00    4.00    --  107.58-125.00 120.00   26
  5  ω     30.00 139.00   1.00    4.00    --  107.58 -15.00   0.00  109
  6  ω    143.00 168.00   1.00    4.00    --  107.58 125.00 -60.00   25
  7  ω    -95.00 -10.00   1.00    2.00    --  -41.11   0.00 120.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0426369000
_diffrn_orient_matrix_UB_12      -0.0668711000
_diffrn_orient_matrix_UB_13      -0.0821495000
_diffrn_orient_matrix_UB_21      0.0956008000
_diffrn_orient_matrix_UB_22      -0.1011507000
_diffrn_orient_matrix_UB_23      0.0431799000
_diffrn_orient_matrix_UB_31      -0.2150291000
_diffrn_orient_matrix_UB_32      -0.0317120000
_diffrn_orient_matrix_UB_33      0.0355400000
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.525
_reflns_Friedel_fraction_full    0.789
_reflns_Friedel_fraction_max     0.722
_reflns_number_gt                1948
_reflns_number_total             2152
_reflns_odcompleteness_completeness 100.00
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 631 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.092
_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)+(0.0504P)²+0.1465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1106
_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 Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.0137(4) 0.4444(2) 0.43998(17) 0.0510(7) Uani 1 1 d . . . . .
O3 O 0.1222(3) 0.59699(18) 0.50204(15) 0.0387(5) Uani 1 1 d . . . . .
N1 N 0.5192(4) 0.3143(2) 0.56906(17) 0.0349(6) Uani 1 1 d . . . . .
H1 H 0.596(6) 0.254(4) 0.565(3) 0.055(12) Uiso 1 1 d . . . . .
N2 N 0.3644(4) 0.3325(2) 0.51357(18) 0.0372(6) Uani 1 1 d . . . . .
C1 C 0.7369(4) 0.3947(2) 0.68358(18) 0.0236(5) Uani 1 1 d . . . . .
C2 C 0.7139(4) 0.4394(2) 0.76577(18) 0.0270(6) Uani 1 1 d . . . . .
H2 H 0.589532 0.472735 0.780956 0.032 Uiso 1 1 calc R U . . .
C3 C 0.8748(5) 0.4344(2) 0.82484(19) 0.0312(6) Uani 1 1 d . . . . .
H3 H 0.860428 0.466434 0.878813 0.037 Uiso 1 1 calc R U . . .
C4 C 1.0585(5) 0.3811(2) 0.8030(2) 0.0318(6) Uani 1 1 d . . . . .
H4 H 1.166640 0.377016 0.842675 0.038 Uiso 1 1 calc R U . . .
C5 C 1.0801(4) 0.3342(2) 0.7224(2) 0.0299(6) Uani 1 1 d . . . . .
H5 H 1.202446 0.298130 0.708239 0.036 Uiso 1 1 calc R U . . .
C6 C 0.9205(4) 0.3406(2) 0.66290(19) 0.0266(6) Uani 1 1 d . . . . .
H6 H 0.935825 0.308730 0.608897 0.032 Uiso 1 1 calc R U . . .
C7 C 0.5684(4) 0.4018(2) 0.61959(18) 0.0242(5) Uani 1 1 d . . . . .
C8 C 0.4331(4) 0.4835(2) 0.59450(17) 0.0216(5) Uani 1 1 d . . . . .
C9 C 0.3127(4) 0.4360(2) 0.52909(18) 0.0275(6) Uani 1 1 d . . . . .
C10 C 0.1409(5) 0.4885(2) 0.4857(2) 0.0337(7) Uani 1 1 d . . . . .
C11 C 0.3032(5) 0.6533(2) 0.5378(2) 0.0346(7) Uani 1 1 d . . . . .
H11A H 0.263231 0.727302 0.551900 0.041 Uiso 1 1 calc R U . . .
H11B H 0.409813 0.657116 0.493740 0.041 Uiso 1 1 calc R U . . .
C12 C 0.3967(4) 0.6007(2) 0.61834(17) 0.0237(5) Uani 1 1 d . . . . .
C13 C 0.2444(5) 0.6120(2) 0.6939(2) 0.0337(7) Uani 1 1 d . . . . .
H13A H 0.116036 0.576469 0.679712 0.051 Uiso 1 1 calc R U . . .
H13B H 0.218744 0.687625 0.704901 0.051 Uiso 1 1 calc R U . . .
H13C H 0.303148 0.578900 0.744398 0.051 Uiso 1 1 calc R U . . .
C14 C 0.5978(5) 0.6628(2) 0.6376(2) 0.0364(7) Uani 1 1 d . . . . .
H14A H 0.652000 0.639952 0.692346 0.055 Uiso 1 1 calc R U . . .
H14B H 0.569354 0.739428 0.639236 0.055 Uiso 1 1 calc R U . . .
H14C H 0.698042 0.647990 0.593302 0.055 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 C10 1.211(4) . ?
O3 C10 1.364(4) . ?
O3 C11 1.465(4) . ?
N1 H1 0.89(4) . ?
N1 N2 1.336(4) . ?
N1 C7 1.368(4) . ?
N2 C9 1.337(4) . ?
C1 C2 1.396(4) . ?
C1 C6 1.393(4) . ?
C1 C7 1.473(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.385(4) . ?
C8 C9 1.403(4) . ?
C8 C12 1.506(3) . ?
C9 C10 1.446(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.530(4) . ?
C12 C13 1.534(4) . ?
C12 C14 1.532(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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 O3 C11 117.6(2) . . ?
N2 N1 H1 120(3) . . ?
N2 N1 C7 114.2(2) . . ?
C7 N1 H1 124(3) . . ?
N1 N2 C9 103.2(2) . . ?
C2 C1 C7 120.9(2) . . ?
C6 C1 C2 119.2(3) . . ?
C6 C1 C7 119.9(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.7(3) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
N1 C7 C1 120.6(2) . . ?
N1 C7 C8 105.3(2) . . ?
C8 C7 C1 134.1(2) . . ?
C7 C8 C9 104.4(2) . . ?
C7 C8 C12 136.3(2) . . ?
C9 C8 C12 119.3(2) . . ?
N2 C9 C8 112.9(3) . . ?
N2 C9 C10 122.0(3) . . ?
C8 C9 C10 124.9(3) . . ?
O1 C10 O3 119.1(3) . . ?
O1 C10 C9 126.2(3) . . ?
O3 C10 C9 114.7(3) . . ?
O3 C11 H11A 108.5 . . ?
O3 C11 H11B 108.5 . . ?
O3 C11 C12 115.0(2) . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
C8 C12 C11 105.4(2) . . ?
C8 C12 C13 111.9(2) . . ?
C8 C12 C14 113.2(2) . . ?
C11 C12 C13 109.5(2) . . ?
C11 C12 C14 106.3(2) . . ?
C14 C12 C13 110.2(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C11 C12 C8 52.3(3) . . . . ?
O3 C11 C12 C13 -68.3(3) . . . . ?
O3 C11 C12 C14 172.7(2) . . . . ?
N1 N2 C9 C8 -0.4(3) . . . . ?
N1 N2 C9 C10 -176.5(3) . . . . ?
N1 C7 C8 C9 -0.3(3) . . . . ?
N1 C7 C8 C12 -178.2(3) . . . . ?
N2 N1 C7 C1 -179.6(3) . . . . ?
N2 N1 C7 C8 0.1(3) . . . . ?
N2 C9 C10 O1 8.8(5) . . . . ?
N2 C9 C10 O3 -173.5(3) . . . . ?
C1 C2 C3 C4 -2.2(4) . . . . ?
C1 C7 C8 C9 179.3(3) . . . . ?
C1 C7 C8 C12 1.4(6) . . . . ?
C2 C1 C6 C5 -1.8(4) . . . . ?
C2 C1 C7 N1 -137.7(3) . . . . ?
C2 C1 C7 C8 42.7(5) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C6 C1 C2 C3 2.9(4) . . . . ?
C6 C1 C7 N1 40.8(4) . . . . ?
C6 C1 C7 C8 -138.7(3) . . . . ?
C7 N1 N2 C9 0.2(3) . . . . ?
C7 C1 C2 C3 -178.6(3) . . . . ?
C7 C1 C6 C5 179.6(2) . . . . ?
C7 C8 C9 N2 0.4(3) . . . . ?
C7 C8 C9 C10 176.4(3) . . . . ?
C7 C8 C12 C11 152.6(3) . . . . ?
C7 C8 C12 C13 -88.4(4) . . . . ?
C7 C8 C12 C14 36.8(4) . . . . ?
C8 C9 C10 O1 -166.9(3) . . . . ?
C8 C9 C10 O3 10.8(4) . . . . ?
C9 C8 C12 C11 -25.1(3) . . . . ?
C9 C8 C12 C13 93.9(3) . . . . ?
C9 C8 C12 C14 -140.9(3) . . . . ?
C10 O3 C11 C12 -52.1(4) . . . . ?
C11 O3 C10 O1 -164.4(3) . . . . ?
C11 O3 C10 C9 17.7(4) . . . . ?
C12 C8 C9 N2 178.8(3) . . . . ?
C12 C8 C9 C10 -5.2(4) . . . . ?

_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 1.291
_oxdiff_exptl_absorpt_empirical_full_min 0.665
####################################################################### 
# 
# 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_242-3
_database_code_depnum_ccdc_archive 'CCDC 2167331'
loop_
_audit_author_name
_audit_author_address
LFYzznhz
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-04-19 deposited with the CCDC.	2023-02-10 downloaded from the CCDC.
;
_audit_creation_date             2021-06-24
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H21 Cl O2'
_chemical_formula_sum            'C21 H21 Cl O2'
_chemical_formula_weight         340.83
_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 0.0033 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'
Cl Cl 0.1484 0.1585 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   10.2977(7)
_cell_length_b                   17.5607(12)
_cell_length_c                   19.3729(13)
_cell_angle_alpha                90
_cell_angle_beta                 96.121(6)
_cell_angle_gamma                90
_cell_volume                     3483.3(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4220
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      28.7810
_cell_measurement_theta_min      2.6270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43450
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7517
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.115
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00  83.00   1.00    3.00    --   12.05  57.00   0.00   83
  2  ω    -22.00  36.00   1.00    3.00    --   12.05 -38.00-150.00   58
  3  ω    -57.00 -27.00   1.00    3.00    --   12.05 -38.00-150.00   30
  4  ω     38.00  64.00   1.00    3.00    --   12.05-178.00-180.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0057159000
_diffrn_orient_matrix_UB_12      -0.0078129000
_diffrn_orient_matrix_UB_13      0.0354818000
_diffrn_orient_matrix_UB_21      0.0638741000
_diffrn_orient_matrix_UB_22      -0.0156534000
_diffrn_orient_matrix_UB_23      0.0036796000
_diffrn_orient_matrix_UB_31      0.0261678000
_diffrn_orient_matrix_UB_32      0.0364089000
_diffrn_orient_matrix_UB_33      0.0091371000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2641
_reflns_number_total             3066
_reflns_odcompleteness_completeness 99.97
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3066
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.023
_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)+(0.0406P)²+2.6474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0920
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C14(H14), C15(H15), C17(H17),
 C18(H18)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_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
Cl1 Cl 0.16559(4) 0.52399(3) 0.27076(2) 0.04027(16) Uani 1 1 d . . . . .
O1 O 0.84970(12) 0.24756(7) 0.33923(6) 0.0420(3) Uani 1 1 d . . . . .
O2 O 0.71731(10) 0.34322(6) 0.35221(5) 0.0275(3) Uani 1 1 d . . . . .
C1 C 1.04353(17) 0.34139(9) 0.58089(8) 0.0304(4) Uani 1 1 d . . . . .
C2 C 1.15592(17) 0.33190(10) 0.54756(9) 0.0360(4) Uani 1 1 d . . . . .
H2 H 1.153420 0.343182 0.500533 0.043 Uiso 1 1 calc R U . . .
C3 C 1.27144(19) 0.30593(11) 0.58322(11) 0.0426(5) Uani 1 1 d . . . . .
H3 H 1.345360 0.300373 0.559970 0.051 Uiso 1 1 calc R U . . .
C4 C 1.2776(2) 0.28831(10) 0.65275(10) 0.0437(5) Uani 1 1 d . . . . .
H4 H 1.354980 0.270614 0.676448 0.052 Uiso 1 1 calc R U . . .
C5 C 1.1681(2) 0.29715(11) 0.68674(10) 0.0462(5) Uani 1 1 d . . . . .
H5 H 1.171378 0.285278 0.733678 0.055 Uiso 1 1 calc R U . . .
C6 C 1.0528(2) 0.32364(10) 0.65153(9) 0.0401(5) Uani 1 1 d . . . . .
H6 H 0.979897 0.329742 0.675473 0.048 Uiso 1 1 calc R U . . .
C7 C 0.91726(16) 0.37106(9) 0.54903(8) 0.0289(4) Uani 1 1 d . . . . .
H7 H 0.865891 0.392196 0.580760 0.035 Uiso 1 1 calc R U . . .
C8 C 0.86220(15) 0.37351(9) 0.48336(8) 0.0230(3) Uani 1 1 d . . . . .
C9 C 0.72308(15) 0.40480(9) 0.46668(8) 0.0233(3) Uani 1 1 d . . . . .
C10 C 0.69722(15) 0.41497(9) 0.38730(8) 0.0226(3) Uani 1 1 d . . . . .
H10 H 0.760487 0.451920 0.373012 0.027 Uiso 1 1 calc R U . . .
C11 C 0.83011(15) 0.30578(10) 0.36890(8) 0.0270(4) Uani 1 1 d . . . . .
C12 C 0.92733(15) 0.34133(9) 0.42325(8) 0.0259(4) Uani 1 1 d . . . . .
H12 H 0.986729 0.300916 0.441822 0.031 Uiso 1 1 calc R U . . .
C13 C 0.56257(15) 0.44169(9) 0.35988(7) 0.0231(3) Uani 1 1 d . . . . .
C14 C 0.46174(15) 0.39048(10) 0.34222(8) 0.0276(4) Uani 1 1 d . . . . .
H14 H 0.476535 0.338593 0.348638 0.033 Uiso 1 1 calc R U . . .
C15 C 0.33961(15) 0.41570(10) 0.31519(8) 0.0283(4) Uani 1 1 d . . . . .
H15 H 0.272726 0.381141 0.302824 0.034 Uiso 1 1 calc R U . . .
C16 C 0.31845(15) 0.49265(10) 0.30685(8) 0.0269(4) Uani 1 1 d . . . . .
C17 C 0.41597(16) 0.54529(10) 0.32451(8) 0.0288(4) Uani 1 1 d . . . . .
H17 H 0.399973 0.597192 0.319154 0.035 Uiso 1 1 calc R U . . .
C18 C 0.53806(16) 0.51883(9) 0.35039(8) 0.0267(4) Uani 1 1 d . . . . .
H18 H 0.605187 0.553547 0.361662 0.032 Uiso 1 1 calc R U . . .
C19 C 0.70909(18) 0.48294(10) 0.50003(9) 0.0316(4) Uani 1 1 d . . . . .
H19A H 0.727217 0.478593 0.549517 0.047 Uiso 1 1 calc R U . . .
H19B H 0.621632 0.501336 0.488678 0.047 Uiso 1 1 calc R U . . .
H19C H 0.769642 0.517918 0.482822 0.047 Uiso 1 1 calc R U . . .
C20 C 0.62475(16) 0.34887(10) 0.49300(9) 0.0321(4) Uani 1 1 d . . . . .
H20A H 0.632920 0.300165 0.471385 0.048 Uiso 1 1 calc R U . . .
H20B H 0.537718 0.367920 0.481623 0.048 Uiso 1 1 calc R U . . .
H20C H 0.642173 0.343588 0.542443 0.048 Uiso 1 1 calc R U . . .
C21 C 1.00947(17) 0.39993(12) 0.38702(9) 0.0390(5) Uani 1 1 d . . . . .
H21A H 0.952397 0.436100 0.362091 0.059 Uiso 1 1 calc R U . . .
H21B H 1.059618 0.373997 0.355209 0.059 Uiso 1 1 calc R U . . .
H21C H 1.067359 0.426039 0.421269 0.059 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
Cl1 C16 1.7421(16) . ?
O1 C11 1.200(2) . ?
O2 C10 1.4569(18) . ?
O2 C11 1.3439(19) . ?
C1 C2 1.394(3) . ?
C1 C6 1.397(2) . ?
C1 C7 1.474(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.337(2) . ?
C8 C9 1.536(2) . ?
C8 C12 1.514(2) . ?
C9 C10 1.543(2) . ?
C9 C19 1.530(2) . ?
C9 C20 1.536(2) . ?
C10 H10 0.9800 . ?
C10 C13 1.506(2) . ?
C11 C12 1.509(2) . ?
C12 H12 0.9800 . ?
C12 C21 1.547(2) . ?
C13 C14 1.389(2) . ?
C13 C18 1.387(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.375(2) . ?
C16 C17 1.381(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(2) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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
C11 O2 C10 118.23(12) . . ?
C2 C1 C6 116.97(16) . . ?
C2 C1 C7 125.96(15) . . ?
C6 C1 C7 117.03(16) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.24(17) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.55(19) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.29(17) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.39(18) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 119.2 . . ?
C5 C6 C1 121.54(19) . . ?
C5 C6 H6 119.2 . . ?
C1 C7 H7 113.8 . . ?
C8 C7 C1 132.50(16) . . ?
C8 C7 H7 113.8 . . ?
C7 C8 C9 120.19(14) . . ?
C7 C8 C12 122.83(15) . . ?
C12 C8 C9 116.84(12) . . ?
C8 C9 C10 107.99(12) . . ?
C8 C9 C20 109.54(13) . . ?
C19 C9 C8 111.08(13) . . ?
C19 C9 C10 107.64(13) . . ?
C19 C9 C20 109.76(13) . . ?
C20 C9 C10 110.80(13) . . ?
O2 C10 C9 110.30(12) . . ?
O2 C10 H10 108.0 . . ?
O2 C10 C13 106.02(12) . . ?
C9 C10 H10 108.0 . . ?
C13 C10 C9 116.24(12) . . ?
C13 C10 H10 108.0 . . ?
O1 C11 O2 119.11(15) . . ?
O1 C11 C12 123.63(15) . . ?
O2 C11 C12 117.24(14) . . ?
C8 C12 H12 107.4 . . ?
C8 C12 C21 114.16(14) . . ?
C11 C12 C8 112.08(13) . . ?
C11 C12 H12 107.4 . . ?
C11 C12 C21 108.23(13) . . ?
C21 C12 H12 107.4 . . ?
C14 C13 C10 121.43(14) . . ?
C18 C13 C10 119.92(14) . . ?
C18 C13 C14 118.63(15) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.80(16) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 120.5 . . ?
C16 C15 C14 119.04(16) . . ?
C16 C15 H15 120.5 . . ?
C15 C16 Cl1 118.85(13) . . ?
C15 C16 C17 121.78(15) . . ?
C17 C16 Cl1 119.34(13) . . ?
C16 C17 H17 120.9 . . ?
C16 C17 C18 118.28(16) . . ?
C18 C17 H17 120.9 . . ?
C13 C18 H18 119.3 . . ?
C17 C18 C13 121.45(15) . . ?
C17 C18 H18 119.3 . . ?
C9 C19 H19A 109.5 . . ?
C9 C19 H19B 109.5 . . ?
C9 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C9 C20 H20A 109.5 . . ?
C9 C20 H20B 109.5 . . ?
C9 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C12 C21 H21A 109.5 . . ?
C12 C21 H21B 109.5 . . ?
C12 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C16 C17 C18 -177.35(12) . . . . ?
O1 C11 C12 C8 -139.75(17) . . . . ?
O1 C11 C12 C21 93.5(2) . . . . ?
O2 C10 C13 C14 34.07(18) . . . . ?
O2 C10 C13 C18 -144.50(14) . . . . ?
O2 C11 C12 C8 42.03(19) . . . . ?
O2 C11 C12 C21 -84.74(17) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C1 C7 C8 C9 176.52(16) . . . . ?
C1 C7 C8 C12 1.0(3) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
C2 C1 C7 C8 24.1(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C6 C1 C7 C8 -158.25(18) . . . . ?
C7 C1 C2 C3 177.67(16) . . . . ?
C7 C1 C6 C5 -178.41(16) . . . . ?
C7 C8 C9 C10 169.11(14) . . . . ?
C7 C8 C9 C19 51.29(19) . . . . ?
C7 C8 C9 C20 -70.13(18) . . . . ?
C7 C8 C12 C11 143.94(16) . . . . ?
C7 C8 C12 C21 -92.56(19) . . . . ?
C8 C9 C10 O2 56.37(15) . . . . ?
C8 C9 C10 C13 177.06(13) . . . . ?
C9 C8 C12 C11 -31.77(19) . . . . ?
C9 C8 C12 C21 91.73(16) . . . . ?
C9 C10 C13 C14 -88.89(17) . . . . ?
C9 C10 C13 C18 92.54(17) . . . . ?
C10 O2 C11 O1 -178.12(14) . . . . ?
C10 O2 C11 C12 0.2(2) . . . . ?
C10 C13 C14 C15 -178.08(14) . . . . ?
C10 C13 C18 C17 179.20(14) . . . . ?
C11 O2 C10 C9 -51.59(17) . . . . ?
C11 O2 C10 C13 -178.22(12) . . . . ?
C12 C8 C9 C10 -15.06(18) . . . . ?
C12 C8 C9 C19 -132.88(14) . . . . ?
C12 C8 C9 C20 105.70(15) . . . . ?
C13 C14 C15 C16 -0.9(2) . . . . ?
C14 C13 C18 C17 0.6(2) . . . . ?
C14 C15 C16 Cl1 178.41(12) . . . . ?
C14 C15 C16 C17 0.2(2) . . . . ?
C15 C16 C17 C18 0.8(2) . . . . ?
C16 C17 C18 C13 -1.2(2) . . . . ?
C18 C13 C14 C15 0.5(2) . . . . ?
C19 C9 C10 O2 176.37(12) . . . . ?
C19 C9 C10 C13 -62.93(17) . . . . ?
C20 C9 C10 O2 -63.60(16) . . . . ?
C20 C9 C10 C13 57.09(18) . . . . ?

_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 1.564
_oxdiff_exptl_absorpt_empirical_full_min 0.496
