# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_exp_623
_database_code_depnum_ccdc_archive 'CCDC 1981383'
loop_
_audit_author_name
_audit_author_address
'Junliang Zhang'
;East China Normal University
China
;
_audit_update_record             
;
2020-02-02 deposited with the CCDC.	2020-10-02 downloaded from the CCDC.
;
_audit_creation_date             2019-01-07
_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        ?
_chemical_formula_moiety         'C20 H21 N O2 S'
_chemical_formula_sum            'C20 H21 N O2 S'
_chemical_formula_weight         339.44
_chemical_absolute_configuration ad
_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'
S S 0.3331 0.5567 '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      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   6.0451(5)
_cell_length_b                   8.3029(4)
_cell_length_c                   9.2867(5)
_cell_angle_alpha                107.436(5)
_cell_angle_beta                 107.421(7)
_cell_angle_gamma                90.517(6)
_cell_volume                     421.80(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4404
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.9950
_cell_measurement_theta_min      5.5960
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.793
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             180
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5537
_diffrn_reflns_point_group_measured_fraction_full 0.861
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        67.049
_diffrn_reflns_theta_max         67.048
_diffrn_reflns_theta_min         5.263
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -1.00  29.00   1.00    1.00    --    0.00  38.00  60.00   30
  2  ω     23.00  69.00   1.00    1.00    --    0.00  38.00 -60.00   46
  3  ω     56.00  84.00   1.00    1.00    --    0.00  77.00 -60.00   28
  4  ω    -22.00  88.00   1.00    1.00    --    0.00  19.00-150.00  110
  5  ω    -22.00  37.00   1.00    1.00    --    0.00  57.00  90.00   59
  6  ω    -27.00   3.00   1.00    1.00    --    0.00  77.00 -60.00   30
  7  ω      9.00  56.00   1.00    1.00    --    0.00  77.00 -30.00   47
  8  ω    -29.00   2.00   1.00    1.00    --    0.00  77.00 -30.00   31
  9  ω    -18.00   7.00   1.00    1.00    --    0.00  38.00 -60.00   25
 10  ω     49.00  87.00   1.00    1.00    --    0.00  57.00  90.00   38
 11  ω     52.00 123.00   1.00    1.00    --   95.80 -82.00-120.00   71
 12  ω    129.00 178.00   1.00    1.00    --   95.80  45.00  90.00   49
 13  ω     64.00  92.00   1.00    1.00    --   95.80  82.00 -90.00   28
 14  ω     65.00 108.00   1.00    1.00    --   95.80  77.00-150.00   43
 15  ω     77.00 105.00   1.00    1.00    --   95.80  45.00  90.00   28
 16  ω     71.00  97.00   1.00    1.00    --   95.80  61.00 -30.00   26
 17  ω     63.00  91.00   1.00    1.00    --   95.80  82.00  30.00   28
 18  ω    123.00 177.00   1.00    1.00    --   95.80  61.00   0.00   54
 19  ω      9.00  53.00   1.00    1.00    --   95.80 -82.00  90.00   44
 20  ω     63.00 105.00   1.00    1.00    --   95.80  82.00-180.00   42
 21  ω     67.00 126.00   1.00    1.00    --   95.80 -82.00  90.00   59
 22  ω     65.00  92.00   1.00    1.00    --   95.80  77.00 -30.00   27
 23  ω    115.00 184.00   1.00    1.00    --   95.80  77.00 -30.00   69
 24  ω     71.00 140.00   1.00    1.00    --   95.80  61.00 150.00   69
 25  ω     63.00  99.00   1.00    1.00    --   95.80  82.00  60.00   36
 26  ω     66.00  92.00   1.00    1.00    --   95.80  77.00 150.00   26
 27  ω    100.00 184.00   1.00    1.00    --   95.80  82.00 -90.00   84
 28  ω     63.00  89.00   1.00    1.00    --   95.80  82.00   0.00   26
 29  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 -60.00   25
 30  ω     72.00 108.00   1.00    1.00    --   95.80  61.00 120.00   36
 31  ω     71.00  97.00   1.00    1.00    --   95.80  61.00   0.00   26
 32  ω      7.00 100.00   1.00    1.00    --   95.80 -82.00  60.00   93
 33  ω     76.00 146.00   1.00    1.00    --   95.80  45.00-150.00   70
 34  ω     74.00 128.00   1.00    1.00    --   95.80 -82.00-180.00   54
 35  ω     40.00  66.00   1.00    1.00    --   95.80 -82.00-180.00   26
 36  ω    112.00 185.00   1.00    1.00    --   95.80  77.00 120.00   73
 37  ω     64.00  91.00   1.00    1.00    --   95.80  82.00 150.00   27
 38  ω     75.00 107.00   1.00    1.00    --   95.80  45.00 -90.00   32
 39  ω    119.00 180.00   1.00    1.00    --   95.80  45.00 -90.00   61
 40  ω     75.00 118.00   1.00    1.00    --   95.80  45.00 -30.00   43
 41  ω     76.00 111.00   1.00    1.00    --   95.80  45.00   0.00   35
 42  ω     75.00 108.00   1.00    1.00    --   95.80  45.00  60.00   33
 43  ω    136.00 185.00   1.00    1.00    --   95.80  45.00  60.00   49
 44  ω     71.00  97.00   1.00    1.00    --   95.80  61.00 -90.00   26
 45  ω     66.00  92.00   1.00    1.00    --   95.80  77.00  60.00   26
 46  ω     66.00  92.00   1.00    1.00    --   95.80  77.00  90.00   26
 47  ω     66.00  91.00   1.00    1.00    --   95.80  82.00-150.00   25
 48  ω     82.00 107.00   1.00    1.00    --   95.80  30.00 -60.00   25
 49  ω    138.00 163.00   1.00    1.00    --   95.80  30.00 -60.00   25
 50  ω     75.00 104.00   1.00    1.00    --   95.80  45.00  30.00   29
 51  ω    141.00 180.00   1.00    1.00    --   95.80  45.00  30.00   39
 52  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 53  ω     66.00  92.00   1.00    1.00    --   95.80  77.00 120.00   26
 54  ω    125.00 179.00   1.00    1.00    --   95.80  77.00 150.00   54
 55  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 56  ω    136.00 162.00   1.00    1.00    --   95.80  77.00-150.00   26
 57  ω     79.00 116.00   1.00    1.00    --   95.80 -82.00 -30.00   37
 58  ω    156.00 181.00   1.00    1.00    --   95.80  82.00  30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1044239000
_diffrn_orient_matrix_UB_12      0.1334403000
_diffrn_orient_matrix_UB_13      -0.0781817000
_diffrn_orient_matrix_UB_21      -0.0914335000
_diffrn_orient_matrix_UB_22      -0.1399386000
_diffrn_orient_matrix_UB_23      -0.1626203000
_diffrn_orient_matrix_UB_31      -0.2300545000
_diffrn_orient_matrix_UB_32      -0.0297218000
_diffrn_orient_matrix_UB_33      0.0323288000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    0.737
_reflns_Friedel_fraction_max     0.737
_reflns_number_gt                2458
_reflns_number_total             2596
_reflns_odcompleteness_completeness 98.67
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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         0.742
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2596
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0645
_refine_ls_restrained_S_all      1.072
_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)+(0.1441P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1717
_refine_ls_wR_factor_ref         0.1754
_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:
 C1(H1), C2(H2), C5(H5), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C15(H15), C16(H16), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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
S1 S 0.66998(13) 0.59659(10) 0.34642(10) 0.0199(4) Uani 1 1 d . . . . .
O1 O 0.9088(7) 0.5675(5) 0.3760(4) 0.0255(9) Uani 1 1 d . . . . .
O2 O 0.5731(8) 0.6984(5) 0.2485(5) 0.0266(9) Uani 1 1 d . . . . .
N1 N 0.6342(8) 0.6918(5) 0.5185(5) 0.0211(10) Uani 1 1 d . . . . .
C1 C 0.3703(10) 0.7867(7) 0.6724(6) 0.0223(11) Uani 1 1 d . . . . .
H1 H 0.206566 0.742876 0.643740 0.027 Uiso 1 1 calc R . . . .
C2 C 0.4237(11) 0.9738(7) 0.7835(7) 0.0250(13) Uani 1 1 d . . . . .
H2 H 0.445962 0.987836 0.895741 0.030 Uiso 1 1 calc R . . . .
C3 C 0.2366(13) 1.0760(9) 0.7097(8) 0.0352(16) Uani 1 1 d . . . . .
H3A H 0.244273 1.188469 0.783508 0.042 Uiso 1 1 calc R . . . .
H3B H 0.081408 1.017991 0.678407 0.042 Uiso 1 1 calc R . . . .
C4 C 0.3008(12) 1.0855(8) 0.5625(8) 0.0329(15) Uani 1 1 d . . . . .
H4A H 0.175129 1.030838 0.464730 0.039 Uiso 1 1 calc R . . . .
H4B H 0.336014 1.202290 0.569429 0.039 Uiso 1 1 calc R . . . .
C5 C 0.5195(11) 0.9886(7) 0.5709(7) 0.0248(12) Uani 1 1 d . . . . .
H5 H 0.618693 1.014292 0.512483 0.030 Uiso 1 1 calc R . . . .
C6 C 0.4361(9) 0.7987(7) 0.5264(6) 0.0204(12) Uani 1 1 d . . . . .
H6 H 0.303565 0.760044 0.428060 0.024 Uiso 1 1 calc R . . . .
C7 C 0.6840(10) 0.6184(6) 0.6453(6) 0.0205(11) Uani 1 1 d . . . . .
C8 C 0.8603(11) 0.5194(7) 0.6847(6) 0.0238(12) Uani 1 1 d . . . . .
H8 H 0.960444 0.487177 0.624613 0.029 Uiso 1 1 calc R . . . .
C9 C 0.8815(11) 0.4697(7) 0.8196(7) 0.0253(12) Uani 1 1 d . . . . .
H9 H 0.997326 0.402024 0.848863 0.030 Uiso 1 1 calc R . . . .
C10 C 0.7352(12) 0.5187(7) 0.9093(7) 0.0262(13) Uani 1 1 d . . . . .
H10 H 0.753361 0.484207 0.998244 0.031 Uiso 1 1 calc R . . . .
C11 C 0.5594(11) 0.6200(7) 0.8679(7) 0.0240(12) Uani 1 1 d . . . . .
H11 H 0.460054 0.653133 0.928409 0.029 Uiso 1 1 calc R . . . .
C12 C 0.5354(10) 0.6703(6) 0.7347(6) 0.0203(12) Uani 1 1 d . . . . .
C13 C 0.6356(11) 1.0354(7) 0.7513(7) 0.0261(12) Uani 1 1 d . . . . .
H13A H 0.767943 0.972933 0.779587 0.031 Uiso 1 1 calc R . . . .
H13B H 0.680727 1.156371 0.802415 0.031 Uiso 1 1 calc R . . . .
C14 C 0.5036(11) 0.3964(7) 0.2676(6) 0.0214(12) Uani 1 1 d . . . . .
C15 C 0.6137(10) 0.2518(7) 0.2807(6) 0.0236(12) Uani 1 1 d . . . . .
H15 H 0.774063 0.259605 0.328288 0.028 Uiso 1 1 calc R . . . .
C16 C 0.4774(11) 0.0956(7) 0.2208(6) 0.0244(12) Uani 1 1 d . . . . .
H16 H 0.548834 -0.001720 0.227941 0.029 Uiso 1 1 calc R . . . .
C17 C 0.2374(11) 0.0821(7) 0.1507(6) 0.0237(13) Uani 1 1 d . . . . .
C18 C 0.1327(11) 0.2289(8) 0.1401(7) 0.0278(13) Uani 1 1 d . . . . .
H18 H -0.028047 0.221833 0.094275 0.033 Uiso 1 1 calc R . . . .
C19 C 0.2652(10) 0.3850(7) 0.1970(6) 0.0229(12) Uani 1 1 d . . . . .
H19 H 0.194019 0.481879 0.187679 0.027 Uiso 1 1 calc R . . . .
C20 C 0.0931(13) -0.0880(8) 0.0887(8) 0.0335(15) Uani 1 1 d . . . . .
H20A H 0.054532 -0.130733 -0.025002 0.050 Uiso 1 1 calc GR . . . .
H20B H -0.047593 -0.075363 0.116873 0.050 Uiso 1 1 calc GR . . . .
H20C H 0.180669 -0.166237 0.134731 0.050 Uiso 1 1 calc GR . . . .


_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
S1 O1 1.424(4) . ?
S1 O2 1.426(4) . ?
S1 N1 1.637(5) . ?
S1 C14 1.764(6) . ?
N1 C6 1.503(7) . ?
N1 C7 1.439(6) . ?
C1 H1 0.9800 . ?
C1 C2 1.554(7) . ?
C1 C6 1.553(8) . ?
C1 C12 1.507(8) . ?
C2 H2 0.9800 . ?
C2 C3 1.540(8) . ?
C2 C13 1.517(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.552(9) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.548(8) . ?
C5 H5 0.9800 . ?
C5 C6 1.543(7) . ?
C5 C13 1.534(8) . ?
C6 H6 0.9800 . ?
C7 C8 1.381(8) . ?
C7 C12 1.387(8) . ?
C8 H8 0.9300 . ?
C8 C9 1.404(9) . ?
C9 H9 0.9300 . ?
C9 C10 1.374(9) . ?
C10 H10 0.9300 . ?
C10 C11 1.396(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.388(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.397(8) . ?
C14 C19 1.382(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.394(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.389(9) . ?
C17 C18 1.394(9) . ?
C17 C20 1.509(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.386(8) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
O1 S1 O2 119.7(3) . . ?
O1 S1 N1 107.4(2) . . ?
O1 S1 C14 107.4(2) . . ?
O2 S1 N1 105.4(2) . . ?
O2 S1 C14 109.1(3) . . ?
N1 S1 C14 107.3(2) . . ?
C6 N1 S1 119.8(4) . . ?
C7 N1 S1 122.8(4) . . ?
C7 N1 C6 109.1(4) . . ?
C2 C1 H1 112.3 . . ?
C6 C1 H1 112.3 . . ?
C6 C1 C2 102.3(4) . . ?
C12 C1 H1 112.3 . . ?
C12 C1 C2 113.4(4) . . ?
C12 C1 C6 103.7(5) . . ?
C1 C2 H2 114.6 . . ?
C3 C2 C1 107.8(5) . . ?
C3 C2 H2 114.6 . . ?
C13 C2 C1 102.1(4) . . ?
C13 C2 H2 114.6 . . ?
C13 C2 C3 101.7(5) . . ?
C2 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
C2 C3 C4 103.1(5) . . ?
H3A C3 H3B 109.1 . . ?
C4 C3 H3A 111.1 . . ?
C4 C3 H3B 111.1 . . ?
C3 C4 H4A 111.1 . . ?
C3 C4 H4B 111.1 . . ?
H4A C4 H4B 109.1 . . ?
C5 C4 C3 103.1(5) . . ?
C5 C4 H4A 111.1 . . ?
C5 C4 H4B 111.1 . . ?
C4 C5 H5 115.2 . . ?
C6 C5 C4 107.0(5) . . ?
C6 C5 H5 115.2 . . ?
C13 C5 C4 101.2(5) . . ?
C13 C5 H5 115.2 . . ?
C13 C5 C6 101.4(4) . . ?
N1 C6 C1 105.6(4) . . ?
N1 C6 C5 111.0(4) . . ?
N1 C6 H6 112.0 . . ?
C1 C6 H6 112.0 . . ?
C5 C6 C1 103.9(4) . . ?
C5 C6 H6 112.0 . . ?
C8 C7 N1 127.5(5) . . ?
C8 C7 C12 122.4(5) . . ?
C12 C7 N1 109.9(5) . . ?
C7 C8 H8 121.5 . . ?
C7 C8 C9 117.0(6) . . ?
C9 C8 H8 121.5 . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.5(6) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.5(6) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.6 . . ?
C12 C11 C10 118.9(6) . . ?
C12 C11 H11 120.6 . . ?
C7 C12 C1 111.6(5) . . ?
C7 C12 C11 119.7(5) . . ?
C11 C12 C1 128.6(5) . . ?
C2 C13 C5 95.3(5) . . ?
C2 C13 H13A 112.7 . . ?
C2 C13 H13B 112.7 . . ?
C5 C13 H13A 112.7 . . ?
C5 C13 H13B 112.7 . . ?
H13A C13 H13B 110.2 . . ?
C15 C14 S1 119.6(5) . . ?
C19 C14 S1 119.6(4) . . ?
C19 C14 C15 120.8(5) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 C14 118.5(5) . . ?
C16 C15 H15 120.8 . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.5(5) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 C18 118.7(5) . . ?
C16 C17 C20 120.5(5) . . ?
C18 C17 C20 120.8(6) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.8(6) . . ?
C19 C18 H18 119.6 . . ?
C14 C19 C18 119.8(5) . . ?
C14 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_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 7.101
_oxdiff_exptl_absorpt_empirical_full_min 0.187
####################################################################### 
# 
# 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_exp_1411
_database_code_depnum_ccdc_archive 'CCDC 2032220'
loop_
_audit_author_name
_audit_author_address
'Junliang Zhang'
;East China Normal University
China
;
_audit_update_record             
;
2020-09-15 deposited with the CCDC.	2020-10-02 downloaded from the CCDC.
;
_audit_creation_date             2020-09-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
(1S,4R,4aR,9aR)-2,3,4,4a,9,9a-hexahydro-1H-1,4-methanocarbazole
_chemical_formula_moiety         'C13 H15 N'
_chemical_formula_sum            'C13 H15 N'
_chemical_formula_weight         185.26
_chemical_absolute_configuration unk
_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'

_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                   8.84190(10)
_cell_length_b                   11.47040(10)
_cell_length_c                   19.67750(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1995.69(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    28253
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.0150
_cell_measurement_theta_min      4.4530
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            47220
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.007
_diffrn_reflns_theta_max         67.007
_diffrn_reflns_theta_min         4.462
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00   2.00   1.00    1.00    --    0.00  82.00 -90.00   33
  2  ω    -89.00 -50.00   1.00    1.00    --    0.00 -38.00-120.00   39
  3  ω     34.00  73.00   1.00    1.00    --    0.00  38.00-180.00   39
  4  ω     57.00  86.00   1.00    1.00    --    0.00  57.00  90.00   29
  5  ω     61.00  86.00   1.00    1.00    --    0.00  57.00-120.00   25
  6  ω     24.00  55.00   1.00    1.00    --    0.00  57.00-120.00   31
  7  ω     48.00  81.00   1.00    1.00    --    0.00  82.00 -90.00   33
  8  ω    -19.00  89.00   1.00    1.00    --    0.00  38.00   0.00  108
  9  ω      6.00  32.00   1.00    1.00    --    0.00  82.00 -90.00   26
 10  ω    -23.00  41.00   1.00    1.00    --    0.00  57.00  90.00   64
 11  ω    -87.00 -35.00   1.00    1.00    --    0.00 -57.00  30.00   52
 12  ω    -13.00  19.00   1.00    1.00    --    0.00 -38.00-120.00   32
 13  ω    -23.00   2.00   1.00    1.00    --    0.00  57.00-120.00   25
 14  ω    -19.00  23.00   1.00    1.00    --    0.00  38.00-180.00   42
 15  ω    -15.00  10.00   1.00    1.00    --    0.00 -57.00  30.00   25
 16  ω     63.00  88.00   1.00    1.00    --   95.80  81.00 107.37   25
 17  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 167.69   25
 18  ω    159.00 184.00   1.00    1.00    --   95.80  61.00 160.72   25
 19  ω    128.00 185.00   1.00    1.00    --   95.80  59.00 -78.66   57
 20  ω     71.00 102.00   1.00    1.00    --   95.80  59.00 -78.66   31
 21  ω    106.00 140.00   1.00    1.00    --   95.80  61.00 160.72   34
 22  ω     65.00  91.00   1.00    1.00    --   95.80  78.00 -37.12   26
 23  ω     65.00 128.00   1.00    1.00    --   95.80 -82.00 -60.00   63
 24  ω     48.00 123.00   1.00    1.00    --   95.80 -82.00  90.00   75
 25  ω     32.00  58.00   1.00    1.00    --   95.80 -82.00 -60.00   26
 26  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 -90.00   26
 27  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 -60.00   25
 28  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-120.00   26
 29  ω    151.00 185.00   1.00    1.00    --   95.80  77.00-120.00   34
 30  ω      6.00 128.00   1.00    1.00    --   95.80 -82.00-120.00  122
 31  ω     64.00 119.00   1.00    1.00    --   95.80  82.00-120.00   55
 32  ω    115.00 185.00   1.00    1.00    --   95.80  77.00  18.26   70
 33  ω     64.00  89.00   1.00    1.00    --   95.80  79.00  -6.76   25
 34  ω     65.00  91.00   1.00    1.00    --   95.80  76.00 131.96   26
 35  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  18.26   26
 36  ω     72.00  98.00   1.00    1.00    --   95.80  61.00 160.72   26
 37  ω     63.00  89.00   1.00    1.00    --   95.80  82.00-150.00   26
 38  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 -90.00   25
 39  ω     71.00  97.00   1.00    1.00    --   95.80  61.00 120.00   26
 40  ω      7.00 123.00   1.00    1.00    --   95.80 -82.00  30.00  116
 41  ω     65.00  90.00   1.00    1.00    --   95.80  77.00  60.00   25
 42  ω     65.00  90.00   1.00    1.00    --   95.80  77.00-180.00   25
 43  ω    127.00 153.00   1.00    1.00    --   95.80  77.00-161.80   26
 44  ω     65.00 129.00   1.00    1.00    --   95.80  77.00-150.00   64
 45  ω     63.00  89.00   1.00    1.00    --   95.80  82.00  30.00   26
 46  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 150.00   25
 47  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 -60.00   26
 48  ω     71.00 185.00   1.00    1.00    --   95.80  61.00  90.00  114
 49  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 50  ω     66.00  91.00   1.00    1.00    --   95.80  77.00-161.80   25
 51  ω    141.00 185.00   1.00    1.00    --   95.80  55.00  73.26   44
 52  ω     63.00  89.00   1.00    1.00    --   95.80  82.00-180.00   26
 53  ω     72.00  98.00   1.00    1.00    --   95.80  61.00 -30.00   26
 54  ω     75.00 114.00   1.00    1.00    --   95.80  45.00 150.00   39
 55  ω     65.00  90.00   1.00    1.00    --   95.80  78.00  85.60   25
 56  ω     75.00 101.00   1.00    1.00    --   95.80  45.00   0.00   26
 57  ω    121.00 147.00   1.00    1.00    --   95.80  45.00   0.00   26
 58  ω     71.00 184.00   1.00    1.00    --   95.80  61.00-180.00  113
 59  ω     71.00 184.00   1.00    1.00    --   95.80  61.00-150.00  113
 60  ω     71.00 174.00   1.00    1.00    --   95.80  61.00  30.00  103
 61  ω    127.00 152.00   1.00    1.00    --   95.80  61.00   0.00   25
 62  ω     77.00 139.00   1.00    1.00    --   95.80  30.00 -30.00   62
 63  ω     71.00 118.00   1.00    1.00    --   95.80  61.00   0.00   47
 64  ω    120.00 179.00   1.00    1.00    --   95.80  81.00 107.37   59
 65  ω     73.00 122.00   1.00    1.00    --   95.80  55.00  73.26   49
 66  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 120.00   26
 67  ω    148.00 173.00   1.00    1.00    --   95.80  77.00 120.00   25
 68  ω     12.00 121.00   1.00    1.00    --   95.80 -82.00-180.00  109
 69  ω    111.00 183.00   1.00    1.00    --   95.80  78.00 -37.12   72
 70  ω     65.00 172.00   1.00    1.00    --   95.80  78.00-131.70  107
 71  ω     70.00 125.00   1.00    1.00    --   95.80  64.00 -49.74   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0341433000
_diffrn_orient_matrix_UB_12      0.0000479000
_diffrn_orient_matrix_UB_13      -0.0767665000
_diffrn_orient_matrix_UB_21      0.0098505000
_diffrn_orient_matrix_UB_22      -0.1340360000
_diffrn_orient_matrix_UB_23      0.0008518000
_diffrn_orient_matrix_UB_31      -0.1706449000
_diffrn_orient_matrix_UB_32      -0.0077626000
_diffrn_orient_matrix_UB_33      -0.0153255000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3485
_reflns_number_total             3553
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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         0.173
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1457 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3553
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0291
_refine_ls_restrained_S_all      1.048
_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)+(0.0366P)²+0.3965P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0731
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Riding coordinates:
 N2(H2A)
2.b Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C11(H11), C12(H12), C20(H20), C21(H21), C22(H22), C25(H25)
2.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C13(H13A,H13B), C23(H23A,H23B), C24(H24A,H24B),
 C26(H26A,H26B)
2.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), N1(H1), C15(H15), C16(H16), C17(H17), C18(H18)
;
_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
C1 C -0.2419(2) 1.04693(14) 0.50687(9) 0.0204(4) Uani 1 1 d . . . . .
C2 C -0.3131(2) 1.04220(15) 0.44370(9) 0.0248(4) Uani 1 1 d . . . . .
H2 H -0.389282 0.988286 0.435096 0.030 Uiso 1 1 calc R . . . .
C3 C -0.2667(2) 1.12064(15) 0.39389(9) 0.0257(4) Uani 1 1 d . . . . .
H3 H -0.312027 1.118349 0.351277 0.031 Uiso 1 1 calc R . . . .
C4 C -0.1543(2) 1.20200(16) 0.40645(9) 0.0259(4) Uani 1 1 d . . . . .
H4 H -0.125056 1.253518 0.372410 0.031 Uiso 1 1 calc R . . . .
C5 C -0.0847(2) 1.20683(15) 0.47033(9) 0.0222(4) Uani 1 1 d . . . . .
H5 H -0.009493 1.261442 0.479118 0.027 Uiso 1 1 calc R . . . .
C6 C -0.1294(2) 1.12958(14) 0.51985(8) 0.0187(4) Uani 1 1 d . . . . .
C7 C -0.07165(19) 1.11443(14) 0.59168(8) 0.0181(4) Uani 1 1 d . . . . .
H7 H 0.037674 1.100432 0.592535 0.022 Uiso 1 1 calc R . . . .
C8 C -0.1178(2) 1.21118(15) 0.64207(8) 0.0202(4) Uani 1 1 d . . . . .
H8 H -0.106414 1.290758 0.624683 0.024 Uiso 1 1 calc R . . . .
C9 C -0.0345(2) 1.18710(16) 0.70925(9) 0.0250(4) Uani 1 1 d . . . . .
H9A H -0.046103 1.251501 0.740774 0.030 Uiso 1 1 calc R . . . .
H9B H 0.072290 1.173090 0.701589 0.030 Uiso 1 1 calc R . . . .
C10 C -0.1152(2) 1.07545(17) 0.73594(9) 0.0261(4) Uani 1 1 d . . . . .
H10A H -0.045421 1.010374 0.738552 0.031 Uiso 1 1 calc R . . . .
H10B H -0.158984 1.088647 0.780488 0.031 Uiso 1 1 calc R . . . .
C11 C -0.2389(2) 1.05286(15) 0.68264(9) 0.0221(4) Uani 1 1 d . . . . .
H11 H -0.324345 1.006181 0.698964 0.026 Uiso 1 1 calc R . . . .
C12 C -0.1625(2) 1.00559(14) 0.61819(8) 0.0200(4) Uani 1 1 d . . . . .
H12 H -0.096058 0.939292 0.627989 0.024 Uiso 1 1 calc R . . . .
C13 C -0.2803(2) 1.17680(15) 0.66035(9) 0.0219(4) Uani 1 1 d . . . . .
H13A H -0.321721 1.223316 0.697062 0.026 Uiso 1 1 calc R . . . .
H13B H -0.347739 1.178147 0.621487 0.026 Uiso 1 1 calc R . . . .
N1 N -0.27004(18) 0.97956(13) 0.56369(7) 0.0249(3) Uani 1 1 d . . . . .
H1 H -0.341461 0.928925 0.566662 0.030 Uiso 1 1 calc R . . . .
C14 C 0.13418(19) 0.82014(14) 0.52377(8) 0.0188(4) Uani 1 1 d . . . . .
C15 C 0.1580(2) 0.78303(15) 0.59014(9) 0.0216(4) Uani 1 1 d . . . . .
H15 H 0.113523 0.714887 0.606171 0.026 Uiso 1 1 calc R . . . .
C16 C 0.2503(2) 0.85052(16) 0.63219(9) 0.0248(4) Uani 1 1 d . . . . .
H16 H 0.265788 0.827689 0.677001 0.030 Uiso 1 1 calc R . . . .
C17 C 0.3192(2) 0.95102(16) 0.60823(9) 0.0257(4) Uani 1 1 d . . . . .
H17 H 0.382118 0.993990 0.636643 0.031 Uiso 1 1 calc R . . . .
C18 C 0.2943(2) 0.98786(15) 0.54150(9) 0.0238(4) Uani 1 1 d . . . . .
H18 H 0.340671 1.055038 0.525174 0.029 Uiso 1 1 calc R . . . .
C19 C 0.2002(2) 0.92340(14) 0.50010(8) 0.0194(4) Uani 1 1 d . . . . .
C20 C 0.1465(2) 0.94804(14) 0.42878(8) 0.0203(4) Uani 1 1 d . . . . .
H20 H 0.091523 1.022119 0.426601 0.024 Uiso 1 1 calc R . . . .
C21 C 0.0393(2) 0.84272(15) 0.41288(8) 0.0199(4) Uani 1 1 d . . . . .
H21 H -0.065172 0.868056 0.405320 0.024 Uiso 1 1 calc R . . . .
C22 C 0.1093(2) 0.79038(15) 0.34864(8) 0.0209(4) Uani 1 1 d . . . . .
H22 H 0.079572 0.709658 0.339251 0.025 Uiso 1 1 calc R . . . .
C23 C 0.0800(2) 0.87614(17) 0.29009(9) 0.0277(4) Uani 1 1 d . . . . .
H23A H -0.024189 0.902508 0.290109 0.033 Uiso 1 1 calc R . . . .
H23B H 0.102496 0.840574 0.246516 0.033 Uiso 1 1 calc R . . . .
C24 C 0.1902(2) 0.97863(16) 0.30523(9) 0.0275(4) Uani 1 1 d . . . . .
H24A H 0.263829 0.987822 0.269089 0.033 Uiso 1 1 calc R . . . .
H24B H 0.135717 1.051336 0.311146 0.033 Uiso 1 1 calc R . . . .
C25 C 0.2663(2) 0.94015(15) 0.37181(9) 0.0213(4) Uani 1 1 d . . . . .
H25 H 0.362089 0.979544 0.381897 0.026 Uiso 1 1 calc R . . . .
C26 C 0.27910(19) 0.80806(15) 0.36179(8) 0.0199(4) Uani 1 1 d . . . . .
H26A H 0.314175 0.767898 0.402208 0.024 Uiso 1 1 calc R . . . .
H26B H 0.341174 0.787126 0.323025 0.024 Uiso 1 1 calc R . . . .
N2 N 0.05204(16) 0.76379(12) 0.47232(7) 0.0201(3) Uani 1 1 d . . . . .
H2A H -0.032943 0.735316 0.485623 0.024 Uiso 1 1 d 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
C1 C2 1.394(2) . ?
C1 C6 1.398(2) . ?
C1 N1 1.382(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.392(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.401(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.375(2) . ?
C6 C7 1.513(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.543(2) . ?
C7 C12 1.573(2) . ?
C8 H8 0.9800 . ?
C8 C9 1.538(2) . ?
C8 C13 1.532(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.557(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.537(3) . ?
C11 H11 0.9800 . ?
C11 C12 1.536(2) . ?
C11 C13 1.532(2) . ?
C12 H12 0.9800 . ?
C12 N1 1.464(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
N1 H1 0.8600 . ?
C14 C15 1.390(2) . ?
C14 C19 1.400(2) . ?
C14 N2 1.404(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.396(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.387(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.397(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.379(3) . ?
C19 C20 1.508(2) . ?
C20 H20 0.9800 . ?
C20 C21 1.567(2) . ?
C20 C25 1.545(2) . ?
C21 H21 0.9800 . ?
C21 C22 1.530(2) . ?
C21 N2 1.483(2) . ?
C22 H22 0.9800 . ?
C22 C23 1.537(2) . ?
C22 C26 1.537(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.555(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.538(2) . ?
C25 H25 0.9800 . ?
C25 C26 1.532(2) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
N2 H2A 0.8601 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.70(16) . . ?
N1 C1 C2 128.19(16) . . ?
N1 C1 C6 111.08(15) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 C1 117.98(17) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.42(16) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.12(16) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 118.98(17) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C7 109.45(14) . . ?
C5 C6 C1 120.79(16) . . ?
C5 C6 C7 129.74(16) . . ?
C6 C7 H7 111.6 . . ?
C6 C7 C8 115.38(14) . . ?
C6 C7 C12 103.22(13) . . ?
C8 C7 H7 111.6 . . ?
C8 C7 C12 102.85(13) . . ?
C12 C7 H7 111.6 . . ?
C7 C8 H8 114.7 . . ?
C9 C8 C7 107.25(14) . . ?
C9 C8 H8 114.7 . . ?
C13 C8 C7 102.34(14) . . ?
C13 C8 H8 114.7 . . ?
C13 C8 C9 101.58(14) . . ?
C8 C9 H9A 111.2 . . ?
C8 C9 H9B 111.2 . . ?
C8 C9 C10 102.61(14) . . ?
H9A C9 H9B 109.2 . . ?
C10 C9 H9A 111.2 . . ?
C10 C9 H9B 111.2 . . ?
C9 C10 H10A 111.0 . . ?
C9 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
C11 C10 C9 103.56(14) . . ?
C11 C10 H10A 111.0 . . ?
C11 C10 H10B 111.0 . . ?
C10 C11 H11 114.6 . . ?
C12 C11 C10 108.05(15) . . ?
C12 C11 H11 114.6 . . ?
C13 C11 C10 102.05(14) . . ?
C13 C11 H11 114.6 . . ?
C13 C11 C12 101.31(13) . . ?
C7 C12 H12 112.0 . . ?
C11 C12 C7 102.61(13) . . ?
C11 C12 H12 112.0 . . ?
N1 C12 C7 104.51(13) . . ?
N1 C12 C11 113.01(15) . . ?
N1 C12 H12 112.0 . . ?
C8 C13 H13A 112.8 . . ?
C8 C13 H13B 112.8 . . ?
C11 C13 C8 94.72(13) . . ?
C11 C13 H13A 112.8 . . ?
C11 C13 H13B 112.8 . . ?
H13A C13 H13B 110.2 . . ?
C1 N1 C12 111.20(13) . . ?
C1 N1 H1 124.4 . . ?
C12 N1 H1 124.4 . . ?
C15 C14 C19 120.57(16) . . ?
C15 C14 N2 127.96(16) . . ?
C19 C14 N2 111.43(15) . . ?
C14 C15 H15 120.8 . . ?
C14 C15 C16 118.39(16) . . ?
C16 C15 H15 120.8 . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 121.09(16) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.13(17) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.4 . . ?
C19 C18 C17 119.21(17) . . ?
C19 C18 H18 120.4 . . ?
C14 C19 C20 109.69(15) . . ?
C18 C19 C14 120.56(16) . . ?
C18 C19 C20 129.71(16) . . ?
C19 C20 H20 111.1 . . ?
C19 C20 C21 103.39(13) . . ?
C19 C20 C25 116.65(14) . . ?
C21 C20 H20 111.1 . . ?
C25 C20 H20 111.1 . . ?
C25 C20 C21 102.98(13) . . ?
C20 C21 H21 111.8 . . ?
C22 C21 C20 102.88(13) . . ?
C22 C21 H21 111.8 . . ?
N2 C21 C20 105.50(13) . . ?
N2 C21 H21 111.8 . . ?
N2 C21 C22 112.41(13) . . ?
C21 C22 H22 114.7 . . ?
C21 C22 C23 107.47(14) . . ?
C21 C22 C26 101.77(13) . . ?
C23 C22 H22 114.7 . . ?
C23 C22 C26 101.89(14) . . ?
C26 C22 H22 114.7 . . ?
C22 C23 H23A 111.0 . . ?
C22 C23 H23B 111.0 . . ?
C22 C23 C24 103.58(14) . . ?
H23A C23 H23B 109.0 . . ?
C24 C23 H23A 111.0 . . ?
C24 C23 H23B 111.0 . . ?
C23 C24 H24A 111.2 . . ?
C23 C24 H24B 111.2 . . ?
H24A C24 H24B 109.1 . . ?
C25 C24 C23 102.73(14) . . ?
C25 C24 H24A 111.2 . . ?
C25 C24 H24B 111.2 . . ?
C20 C25 H25 114.7 . . ?
C24 C25 C20 107.53(14) . . ?
C24 C25 H25 114.7 . . ?
C26 C25 C20 101.65(13) . . ?
C26 C25 C24 101.92(14) . . ?
C26 C25 H25 114.7 . . ?
C22 C26 H26A 112.8 . . ?
C22 C26 H26B 112.8 . . ?
C25 C26 C22 94.60(14) . . ?
C25 C26 H26A 112.8 . . ?
C25 C26 H26B 112.8 . . ?
H26A C26 H26B 110.3 . . ?
C14 N2 C21 109.07(13) . . ?
C14 N2 H2A 114.0 . . ?
C21 N2 H2A 113.9 . . ?

_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 1.771
_oxdiff_exptl_absorpt_empirical_full_min 0.522
####################################################################### 
# 
# 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_exp_1057
_database_code_depnum_ccdc_archive 'CCDC 1981385'
loop_
_audit_author_name
_audit_author_address
'Junliang Zhang'
;East China Normal University
China
;
_audit_update_record             
;
2020-02-02 deposited with the CCDC.	2020-10-02 downloaded from the CCDC.
;
_audit_creation_date             2019-11-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C15 H16 O3'
_chemical_formula_sum            'C15 H16 O3'
_chemical_formula_weight         244.29
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   6.0733(2)
_cell_length_b                   11.5230(3)
_cell_length_c                   17.1932(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1203.23(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10275
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.1490
_cell_measurement_theta_min      4.6190
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3485
_exptl_crystal_description       block
_exptl_crystal_F_000             521.7237
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25516
_diffrn_reflns_theta_full        67.0457
_diffrn_reflns_theta_max         67.05
_diffrn_reflns_theta_min         4.62
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9921
_diffrn_measured_fraction_theta_max 0.9921
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00 -30.00   1.00    1.00    --    0.00 -38.00 120.00   26
  2  ω     48.00  88.00   1.00    1.00    --    0.00  82.00   0.00   40
  3  ω    -19.00  33.00   1.00    1.00    --    0.00  38.00 150.00   52
  4  ω     63.00  88.00   1.00    1.00    --    0.00  38.00 -30.00   25
  5  ω    -76.00 -30.00   1.00    1.00    --    0.00 -19.00-180.00   46
  6  ω    -18.00  47.00   1.00    1.00    --    0.00  38.00 -30.00   65
  7  ω    -30.00  40.00   1.00    1.00    --    0.00  82.00   0.00   70
  8  ω     -8.00  17.00   1.00    1.00    --    0.00 -19.00-180.00   25
  9  ω    -20.00   6.00   1.00    1.00    --    0.00 -38.00 120.00   26
 10  ω    -86.00 -20.00   1.00    1.00    --    0.00 -38.00 -90.00   66
 11  ω     16.00  57.00   1.00    1.00    --    0.00  82.00-120.00   41
 12  ω    -32.00  14.00   1.00    1.00    --    0.00  82.00-120.00   46
 13  ω     44.00  87.00   1.00    1.00    --    0.00  38.00 150.00   43
 14  ω     65.00  90.00   1.00    2.00    --   95.80  77.00  30.00   25
 15  ω    127.00 184.00   1.00    2.00    --   95.80  82.00-120.00   57
 16  ω     65.00  96.00   1.00    2.00    --   95.80  77.00  82.81   31
 17  ω      6.00 120.00   1.00    2.00    --   95.80 -61.00-180.00  114
 18  ω      6.00 128.00   1.00    2.00    --   95.80 -82.00-180.00  122
 19  ω     69.00  95.00   1.00    2.00    --   95.80  67.00 156.33   26
 20  ω     69.00 137.00   1.00    2.00    --   95.80  66.00-179.54   68
 21  ω     65.00  90.00   1.00    2.00    --   95.80  77.00 120.00   25
 22  ω     63.00  98.00   1.00    2.00    --   95.80  82.00 -30.00   35
 23  ω     65.00  90.00   1.00    2.00    --   95.80  77.00  60.00   25
 24  ω     72.00  99.00   1.00    2.00    --   95.80  61.00 -60.00   27
 25  ω     65.00  90.00   1.00    2.00    --   95.80  77.00-180.00   25
 26  ω     63.00  89.00   1.00    2.00    --   95.80  82.00-120.00   26
 27  ω    109.00 185.00   1.00    2.00    --   95.80  82.00 120.00   76
 28  ω     53.00 128.00   1.00    2.00    --   95.80 -82.00  30.00   75
 29  ω     65.00  91.00   1.00    2.00    --   95.80  77.00 -60.00   26
 30  ω     75.00 144.00   1.00    2.00    --   95.80  45.00 -60.00   69
 31  ω     63.00  89.00   1.00    2.00    --   95.80  82.00   0.00   26
 32  ω     71.00 113.00   1.00    2.00    --   95.80  61.00-120.00   42
 33  ω    130.00 179.00   1.00    2.00    --   95.80  82.00 -90.00   49
 34  ω    159.00 185.00   1.00    2.00    --   95.80  44.00 164.83   26
 35  ω    122.00 185.00   1.00    2.00    --   95.80  62.00-105.72   63
 36  ω    109.00 176.00   1.00    2.00    --   95.80  77.00-150.00   67
 37  ω     65.00  91.00   1.00    2.00    --   95.80  77.00-150.00   26
 38  ω     64.00  89.00   1.00    2.00    --   95.80  82.00 -90.00   25
 39  ω     63.00  96.00   1.00    2.00    --   95.80  82.00-180.00   33
 40  ω    122.00 181.00   1.00    2.00    --   95.80  45.00 150.00   59
 41  ω     75.00 103.00   1.00    2.00    --   95.80  45.00 150.00   28
 42  ω     65.00  90.00   1.00    2.00    --   95.80  77.00 -30.00   25
 43  ω     75.00 113.00   1.00    2.00    --   95.80  44.00 164.83   38
 44  ω     67.00  93.00   1.00    2.00    --   95.80  82.00  30.00   26
 45  ω     64.00  90.00   1.00    2.00    --   95.80  82.00  60.00   26
 46  ω     65.00  90.00   1.00    2.00    --   95.80  77.00 -90.00   25
 47  ω     63.00 116.00   1.00    2.00    --   95.80 -82.00 -30.00   53
 48  ω     76.00 107.00   1.00    2.00    --   95.80  45.00  90.00   31
 49  ω     63.00 185.00   1.00    2.00    --   95.80  82.00  90.00  122
 50  ω    106.00 155.00   1.00    2.00    --   95.80  61.00 -60.00   49
 51  ω    112.00 179.00   1.00    2.00    --   95.80  45.00  60.00   67
 52  ω     75.00 108.00   1.00    2.00    --   95.80  45.00  60.00   33
 53  ω     63.00  89.00   1.00    2.00    --   95.80  82.00 -60.00   26
 54  ω     64.00  90.00   1.00    2.00    --   95.80  82.00 120.00   26
 55  ω     65.00  91.00   1.00    2.00    --   95.80  82.00-150.00   26
 56  ω     76.00 102.00   1.00    2.00    --   95.80  45.00-120.00   26
 57  ω    132.00 157.00   1.00    2.00    --   95.80  45.00-120.00   25
 58  ω     75.00 128.00   1.00    2.00    --   95.80  45.00   0.00   53
 59  ω     63.00  89.00   1.00    2.00    --   95.80  82.00 150.00   26
 60  ω    143.00 168.00   1.00    2.00    --   95.80  77.00  82.81   25
 61  ω     70.00  95.00   1.00    2.00    --   95.80  62.00-105.72   25
 62  ω    142.00 169.00   1.00    2.00    --   95.80  43.00  79.28   27
 63  ω     75.00 101.00   1.00    2.00    --   95.80  45.00-180.00   26
 64  ω    141.00 185.00   1.00    2.00    --   95.80  45.00-180.00   44
 65  ω     75.00 183.00   1.00    2.00    --   95.80  45.00  30.00  108
 66  ω     95.00 124.00   1.00    2.00    --   95.80 -82.00-120.00   29
 67  ω     75.00 101.00   1.00    2.00    --   95.80  43.00  79.28   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0186179000
_diffrn_orient_matrix_UB_12      -0.0163705000
_diffrn_orient_matrix_UB_13      -0.0886632000
_diffrn_orient_matrix_UB_21      -0.0161237000
_diffrn_orient_matrix_UB_22      0.1323341000
_diffrn_orient_matrix_UB_23      -0.0113753000
_diffrn_orient_matrix_UB_31      0.2525294000
_diffrn_orient_matrix_UB_32      0.0096834000
_diffrn_orient_matrix_UB_33      0.0058400000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.994
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              20
_reflns_limit_l_min              -20
_reflns_number_gt                2075
_reflns_number_total             2130
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.1678
_refine_diff_density_min         -0.1762
_refine_diff_density_rms         0.0436
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.24(14)
_refine_ls_d_res_high            0.8372
_refine_ls_d_res_low             9.5720
_refine_ls_goodness_of_fit_ref   1.0590
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    27
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.0590
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0534P)²+0.1645P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0863
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C10(H10a,H10b), C13(H13a,H13b)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C2(H2)
2.d Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
O1 O 0.47586(19) 0.13358(8) 0.35626(6) 0.0217(3) Uani 1.000000 .
O2 O 0.1854(2) 0.60768(10) 0.46107(9) 0.0359(3) Uani 1.000000 .
O3 O 0.5263(2) 0.55357(9) 0.42601(6) 0.0229(3) Uani 1.000000 .
C1 C 0.3397(3) 0.22035(12) 0.38078(8) 0.0178(3) Uani 1.000000 .
C2 C 0.4055(3) 0.33404(12) 0.39143(8) 0.0172(3) Uani 1.000000 .
C3 C 0.2489(3) 0.41204(12) 0.42014(8) 0.0171(3) Uani 1.000000 .
C4 C 0.0339(3) 0.37608(12) 0.43686(8) 0.0180(3) Uani 1.000000 .
C5 C -0.0282(3) 0.26108(13) 0.42490(8) 0.0178(3) Uani 1.000000 .
C6 C 0.1259(3) 0.18340(12) 0.39644(8) 0.0169(3) Uani 1.000000 .
C7 C 0.1089(3) 0.05600(12) 0.37868(8) 0.0189(3) Uani 1.000000 .
C8 C -0.0167(3) 0.02485(13) 0.30312(8) 0.0205(3) Uani 1.000000 .
C9 C -0.0332(3) -0.10799(13) 0.29914(10) 0.0241(4) Uani 1.000000 .
C10 C 0.2121(3) -0.14504(13) 0.28626(9) 0.0246(4) Uani 1.000000 .
C11 C 0.3347(3) -0.02822(13) 0.27707(9) 0.0230(4) Uani 1.000000 .
C12 C 0.3525(2) 0.02436(13) 0.35809(9) 0.0195(3) Uani 1.000000 .
C13 C 0.1573(3) 0.04976(13) 0.24020(9) 0.0221(4) Uani 1.000000 .
C14 C 0.3103(3) 0.53444(13) 0.43765(9) 0.0205(3) Uani 1.000000 .
C15 C 0.6055(3) 0.66751(13) 0.44683(11) 0.0278(4) Uani 1.000000 .
H5 H -0.1710(3) 0.23688(13) 0.43585(8) 0.0213(4) Uiso 1.000000 R
H4 H -0.0679(3) 0.42916(12) 0.45604(8) 0.0216(4) Uiso 1.000000 R
H2 H 0.5482(3) 0.35775(12) 0.37997(8) 0.0207(4) Uiso 1.000000 R
H7 H 0.0548(3) 0.01166(12) 0.42342(8) 0.0227(4) Uiso 1.000000 R
H8 H -0.1566(3) 0.06586(13) 0.29609(8) 0.0246(4) Uiso 1.000000 R
H9a H -0.0912(3) -0.13982(13) 0.34718(10) 0.0289(4) Uiso 1.000000 R
H9b H -0.1255(3) -0.13257(13) 0.25616(10) 0.0289(4) Uiso 1.000000 R
H10a H 0.2675(3) -0.18816(13) 0.33058(9) 0.0295(4) Uiso 1.000000 R
H10b H 0.2271(3) -0.19227(13) 0.23987(9) 0.0295(4) Uiso 1.000000 R
H11 H 0.4736(3) -0.03247(13) 0.24817(9) 0.0276(4) Uiso 1.000000 R
H12 H 0.4153(2) -0.03063(13) 0.39549(9) 0.0234(4) Uiso 1.000000 R
H13a H 0.1125(3) 0.02345(13) 0.18899(9) 0.0266(4) Uiso 1.000000 R
H13b H 0.2002(3) 0.13080(13) 0.23833(9) 0.0266(4) Uiso 1.000000 R
H15a H 0.5393(16) 0.72441(17) 0.4134(5) 0.0417(6) Uiso 1.000000 GR
H15b H 0.5671(19) 0.6839(5) 0.4999(3) 0.0417(6) Uiso 1.000000 GR
H15c H 0.7626(4) 0.6701(4) 0.4411(7) 0.0417(6) Uiso 1.000000 GR


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 C1 1.3643(17) . ?
O1 C12 1.4652(17) . ?
O2 C14 1.204(2) . ?
O3 C14 1.346(2) . ?
O3 C15 1.4433(18) . ?
C1 C2 1.382(2) . ?
C1 C6 1.393(2) . ?
C2 C3 1.399(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.399(2) . ?
C3 C14 1.4896(19) . ?
C4 C5 1.393(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.5029(19) . ?
C7 C8 1.549(2) . ?
C7 C12 1.564(2) . ?
C7 H7 0.9800 . ?
C8 C9 1.535(2) . ?
C8 C13 1.539(2) . ?
C8 H8 0.9800 . ?
C9 C10 1.565(2) . ?
C9 H9a 0.9700 . ?
C9 H9b 0.9700 . ?
C10 C11 1.547(2) . ?
C10 H10a 0.9700 . ?
C10 H10b 0.9700 . ?
C11 C12 1.523(2) . ?
C11 C13 1.540(2) . ?
C11 H11 0.9800 . ?
C12 H12 0.9800 . ?
C13 H13a 0.9700 . ?
C13 H13b 0.9700 . ?
C15 H15a 0.9600 . ?
C15 H15b 0.9600 . ?
C15 H15c 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
C12 O1 C1 108.23(11) . . ?
C15 O3 C14 115.91(13) . . ?
C2 C1 O1 124.09(15) . . ?
C6 C1 O1 113.63(12) . . ?
C6 C1 C2 122.26(14) . . ?
C3 C2 C1 117.34(14) . . ?
H2 C2 C1 121.33(10) . . ?
H2 C2 C3 121.33(8) . . ?
C4 C3 C2 121.11(13) . . ?
C14 C3 C2 120.63(14) . . ?
C14 C3 C4 118.19(14) . . ?
C5 C4 C3 120.27(14) . . ?
H4 C4 C3 119.86(8) . . ?
H4 C4 C5 119.86(9) . . ?
C6 C5 C4 118.95(14) . . ?
H5 C5 C4 120.53(9) . . ?
H5 C5 C6 120.53(9) . . ?
C5 C6 C1 120.06(13) . . ?
C7 C6 C1 108.87(13) . . ?
C7 C6 C5 131.06(14) . . ?
C8 C7 C6 115.51(12) . . ?
C12 C7 C6 102.05(12) . . ?
C12 C7 C8 102.81(11) . . ?
H7 C7 C6 111.89(8) . . ?
H7 C7 C8 111.89(8) . . ?
H7 C7 C12 111.89(8) . . ?
C9 C8 C7 107.49(12) . . ?
C13 C8 C7 102.03(12) . . ?
C13 C8 C9 101.50(12) . . ?
H8 C8 C7 114.75(8) . . ?
H8 C8 C9 114.75(9) . . ?
H8 C8 C13 114.75(9) . . ?
C10 C9 C8 102.48(13) . . ?
H9a C9 C8 111.27(9) . . ?
H9a C9 C10 111.27(9) . . ?
H9b C9 C8 111.27(8) . . ?
H9b C9 C10 111.27(8) . . ?
H9b C9 H9a 109.2 . . ?
C11 C10 C9 103.61(12) . . ?
H10a C10 C9 111.04(9) . . ?
H10a C10 C11 111.04(8) . . ?
H10b C10 C9 111.04(8) . . ?
H10b C10 C11 111.04(8) . . ?
H10b C10 H10a 109.0 . . ?
C12 C11 C10 106.67(12) . . ?
C13 C11 C10 102.29(12) . . ?
C13 C11 C12 101.18(12) . . ?
H11 C11 C10 115.01(8) . . ?
H11 C11 C12 115.01(9) . . ?
H11 C11 C13 115.01(8) . . ?
C7 C12 O1 106.77(11) . . ?
C11 C12 O1 110.99(12) . . ?
C11 C12 C7 103.47(12) . . ?
H12 C12 O1 111.74(7) . . ?
H12 C12 C7 111.74(8) . . ?
H12 C12 C11 111.74(8) . . ?
C11 C13 C8 94.72(12) . . ?
H13a C13 C8 112.79(8) . . ?
H13a C13 C11 112.79(8) . . ?
H13b C13 C8 112.79(8) . . ?
H13b C13 C11 112.79(8) . . ?
H13b C13 H13a 110.2 . . ?
O3 C14 O2 123.30(14) . . ?
C3 C14 O2 125.02(16) . . ?
C3 C14 O3 111.66(13) . . ?
H15a C15 O3 109.5 . . ?
H15b C15 O3 109.5 . . ?
H15b C15 H15a 109.5 . . ?
H15c C15 O3 109.5 . . ?
H15c C15 H15a 109.5 . . ?
H15c C15 H15b 109.5 . . ?

_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 4.032
_oxdiff_exptl_absorpt_empirical_full_min 0.439
