# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_1493
_database_code_depnum_ccdc_archive 'CCDC 1880231'
loop_
_audit_author_name
_audit_author_address
'Yongxiang Liu'
;Shenyang Pharmaceutical University
China
;
_audit_update_record             
;
2019-04-17 deposited with the CCDC.	2019-10-18 downloaded from the CCDC.
;
_audit_creation_date             2018-05-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C38 H36 N2 O Si'
_chemical_formula_sum            'C38 H36 N2 O Si'
_chemical_formula_weight         564.78
_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'
Si Si 0.2541 0.3302 '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           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0141(5)
_cell_length_b                   16.8417(6)
_cell_length_c                   18.3913(8)
_cell_angle_alpha                88.276(3)
_cell_angle_beta                 83.244(4)
_cell_angle_gamma                77.357(4)
_cell_volume                     3005.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7751
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4590
_cell_measurement_theta_min      2.3870
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.940
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80927
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0690
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21813
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.628
_diffrn_reflns_theta_min         2.419
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(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 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      8.00  80.00   1.00    1.00    --   40.98 -99.00   0.00   72
  2  ω     35.00  68.00   1.00    1.00    --   40.98-125.00 -60.00   33
  3  ω     44.00  82.00   1.00    1.00    --   40.98-125.00-180.00   38
  4  ω     35.00 136.00   1.00    1.00    --  106.95 -61.00-150.00  101
  5  ω     88.00 117.00   1.00    1.00    --  106.95-125.00 -60.00   29
  6  ω     48.00  93.00   1.00    1.00    --  106.95 -94.00  60.00   45
  7  ω     48.00  99.00   1.00    1.00    --  106.95 -94.00 120.00   51
  8  ω     32.00 105.00   1.00    1.00    --  106.95 -30.00  30.00   73
  9  ω     67.00 178.00   1.00    1.00    --  106.95  15.00 -30.00  111
 10  ω    138.00 165.00   1.00    1.00    --  106.95  77.00   0.00   27
 11  ω    129.00 178.00   1.00    1.00    --  106.95 125.00  60.00   49
 12  ω    109.00 177.00   1.00    1.00    --  106.95 125.00 120.00   68
 13  ω     86.00 113.00   1.00    1.00    --  106.95  77.00   0.00   27
 14  ω     82.00 147.00   1.00    1.00    --  106.95  45.00-120.00   65
 15  ω     75.00 176.00   1.00    1.00    --  106.95  77.00-180.00  101
 16  ω     24.00 104.00   1.00    1.00    --  106.95 -94.00-180.00   80
 17  ω    -81.00  39.00   1.00    1.00    --  -40.98  19.00-120.00  120
 18  ω   -100.00 -64.00   1.00    1.00    --  -40.98-160.00 170.00   36
 19  ω   -110.00 -35.00   1.00    1.00    --  -40.98 -38.00  60.00   75
;
_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      -0.0031243000
_diffrn_orient_matrix_UB_12      0.0109652000
_diffrn_orient_matrix_UB_13      0.0830873000
_diffrn_orient_matrix_UB_21      0.0440162000
_diffrn_orient_matrix_UB_22      -0.0929180000
_diffrn_orient_matrix_UB_23      0.0094866000
_diffrn_orient_matrix_UB_31      0.1524359000
_diffrn_orient_matrix_UB_32      0.0058817000
_diffrn_orient_matrix_UB_33      -0.0110355000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9300
_reflns_number_total             11721
_reflns_odcompleteness_completeness 99.97
_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 (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         0.475
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     763
_refine_ls_number_reflns         11721
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0635
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0937P)²+1.8189P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1769
_refine_ls_wR_factor_ref         0.1928
_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:
 C32(H32A,H32B), C01F(H01A,H01B), C11(H11A,H11B), C10(H10A,H10B), C024(H02D,
 H02E), C026(H02I,H02J)
2.b Aromatic/amide H refined with riding coordinates:
 C31(H31), C15(H15), C2(H2), C00Q(H00Q), C00S(H00S), C00T(H00T), C00U(H00U),
 C21(H21), C14(H14), C22(H22), C011(H011), C25(H25), C30(H30), C016(H016),
 C017(H017), C24(H24), C019(H019), C23(H23), C01C(H01C), C01D(H01D), C3(H3),
 C01H(H01H), C5(H5), C01K(H01K), C01L(H01L), C01M(H01M), C38(H38), C27(H27),
 C01Q(H01Q), C01R(H01R), C01V(H01V), C01W(H01W), C4(H4), C01Z(H01Z), C29(H29),
 C021(H021), C28(H28), C028(H028), C37(H37), C36(H36), C34(H34), C35(H35)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C01X(H01E,H01F,H01G), C023(H02A,
 H02B,H02C), C025(H02F,H02G,H02H), C17(H17A,H17B,H17C)
;
_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
Si1 Si 0.82083(7) 0.59048(4) 0.36147(4) 0.01828(16) Uani 1 1 d . . . . .
Si02 Si 0.23457(7) 0.89105(4) 0.60839(4) 0.01927(16) Uani 1 1 d . . . . .
O003 O 0.56195(18) 0.77841(11) 0.19319(10) 0.0246(4) Uani 1 1 d . . . . .
O004 O 0.47870(19) 0.70345(12) 0.77797(11) 0.0305(4) Uani 1 1 d . . . . .
N1 N 0.7761(2) 0.79937(13) 0.14777(12) 0.0208(4) Uani 1 1 d . . . . .
N006 N -0.1203(2) 0.71673(13) 0.86391(12) 0.0214(4) Uani 1 1 d . . . . .
N2 N 1.1562(2) 0.78629(13) 0.12367(12) 0.0209(4) Uani 1 1 d . . . . .
N008 N 0.2621(2) 0.69430(13) 0.83175(12) 0.0214(4) Uani 1 1 d . . . . .
C9 C 0.9133(2) 0.76939(15) 0.16392(14) 0.0204(5) Uani 1 1 d . . . . .
C7 C 0.9863(3) 0.84348(15) 0.05429(14) 0.0216(5) Uani 1 1 d . . . . .
C12 C 0.6866(3) 0.76393(15) 0.19285(14) 0.0205(5) Uani 1 1 d . . . . .
C26 C 0.9805(2) 0.62507(15) 0.37846(14) 0.0203(5) Uani 1 1 d . . . . .
C1 C 1.2171(3) 0.82044(15) 0.06285(14) 0.0215(5) Uani 1 1 d . . . . .
C31 C 0.9748(3) 0.70798(16) 0.38571(14) 0.0233(5) Uani 1 1 d . . . . .
H31 H 0.893599 0.745111 0.378793 0.028 Uiso 1 1 calc R . . . .
C13 C 0.7753(2) 0.70638(15) 0.24165(13) 0.0196(5) Uani 1 1 d . . . . .
C15 C 0.7237(3) 0.66196(15) 0.29583(14) 0.0207(5) Uani 1 1 d . . . . .
H15 H 0.628646 0.667404 0.301310 0.025 Uiso 1 1 calc R . . . .
C00H C 0.0213(3) 0.70124(15) 0.86772(14) 0.0215(5) Uani 1 1 d . . . . .
C8 C 1.0157(3) 0.80014(15) 0.11712(14) 0.0205(5) Uani 1 1 d . . . . .
C00J C 0.2667(3) 0.77844(15) 0.73118(14) 0.0218(5) Uani 1 1 d . . . . .
C00K C 0.0519(3) 0.87974(15) 0.60888(14) 0.0207(5) Uani 1 1 d . . . . .
C20 C 0.7092(3) 0.59955(15) 0.45233(14) 0.0205(5) Uani 1 1 d . . . . .
C00M C 0.1240(3) 0.72697(15) 0.81724(14) 0.0209(5) Uani 1 1 d . . . . .
C00N C 0.3525(3) 0.72208(15) 0.78152(14) 0.0220(5) Uani 1 1 d . . . . .
C00O C -0.2568(3) 0.84725(16) 0.81763(13) 0.0221(5) Uani 1 1 d . . . . .
C2 C 1.3562(3) 0.82161(16) 0.04343(15) 0.0254(5) Uani 1 1 d . . . . .
H2 H 1.423378 0.797804 0.073053 0.031 Uiso 1 1 calc R . . . .
C00Q C 0.2507(3) 0.89084(15) 0.45287(15) 0.0234(5) Uani 1 1 d . . . . .
H00Q H 0.160575 0.920874 0.460457 0.028 Uiso 1 1 calc R . . . .
C6 C 1.1134(3) 0.85686(15) 0.01858(14) 0.0217(5) Uani 1 1 d . . . . .
C00S C 0.1248(3) 0.77740(15) 0.75856(14) 0.0213(5) Uani 1 1 d . . . . .
H00S H 0.047194 0.806658 0.738931 0.026 Uiso 1 1 calc R . . . .
C00T C 0.3231(3) 0.81650(15) 0.67487(15) 0.0224(5) Uani 1 1 d . . . . .
H00T H 0.418837 0.804524 0.667580 0.027 Uiso 1 1 calc R . . . .
C00U C -0.3886(3) 0.88175(17) 0.80056(15) 0.0256(6) Uani 1 1 d . . . . .
H00U H -0.442825 0.848705 0.785015 0.031 Uiso 1 1 calc R . . . .
C00V C 0.0525(3) 0.65738(16) 0.93007(15) 0.0255(5) Uani 1 1 d . . . . .
C00W C 0.3220(3) 0.86512(15) 0.51346(14) 0.0210(5) Uani 1 1 d . . . . .
C21 C 0.7641(3) 0.61507(16) 0.51560(14) 0.0225(5) Uani 1 1 d . . . . .
H21 H 0.856681 0.617057 0.512485 0.027 Uiso 1 1 calc R . . . .
C14 C 0.9155(3) 0.71386(15) 0.21881(14) 0.0211(5) Uani 1 1 d . . . . .
H14 H 0.993663 0.685389 0.238476 0.025 Uiso 1 1 calc R . . . .
C22 C 0.6835(3) 0.62767(16) 0.58342(15) 0.0258(6) Uani 1 1 d . . . . .
H22 H 0.721976 0.639041 0.624492 0.031 Uiso 1 1 calc R . . . .
C010 C -0.1797(3) 0.68242(15) 0.92514(14) 0.0237(5) Uani 1 1 d . . . . .
C011 C -0.0659(3) 0.93473(16) 0.63961(14) 0.0236(5) Uani 1 1 d . . . . .
H011 H -0.056655 0.983149 0.659420 0.028 Uiso 1 1 calc R . . . .
C16 C 0.8561(3) 0.48409(16) 0.32074(15) 0.0247(5) Uani 1 1 d . . . . .
C25 C 0.5704(3) 0.59555(16) 0.46019(15) 0.0243(5) Uani 1 1 d . . . . .
H25 H 0.530492 0.585270 0.419269 0.029 Uiso 1 1 calc R . . . .
C30 C 1.0862(3) 0.73628(16) 0.40286(15) 0.0254(5) Uani 1 1 d . . . . .
H30 H 1.079827 0.791965 0.406628 0.030 Uiso 1 1 calc R . . . .
C33 C 1.2698(3) 0.65489(17) 0.17970(15) 0.0261(6) Uani 1 1 d . . . . .
C016 C 0.0323(3) 0.80804(17) 0.57915(15) 0.0265(6) Uani 1 1 d . . . . .
H016 H 0.108505 0.770602 0.558034 0.032 Uiso 1 1 calc R . . . .
C017 C -0.1785(3) 0.89767(17) 0.84291(15) 0.0258(6) Uani 1 1 d . . . . .
H017 H -0.090737 0.875255 0.855405 0.031 Uiso 1 1 calc R . . . .
C24 C 0.4908(3) 0.60652(17) 0.52739(16) 0.0279(6) Uani 1 1 d . . . . .
H24 H 0.398982 0.602691 0.531167 0.033 Uiso 1 1 calc R . . . .
C019 C -0.1957(3) 0.91822(17) 0.64100(16) 0.0287(6) Uani 1 1 d . . . . .
H019 H -0.272599 0.955444 0.661705 0.034 Uiso 1 1 calc R . . . .
C23 C 0.5469(3) 0.62317(16) 0.58912(15) 0.0262(6) Uani 1 1 d . . . . .
H23 H 0.492680 0.631245 0.634059 0.031 Uiso 1 1 calc R . . . .
C01B C -0.0737(3) 0.64474(16) 0.96773(15) 0.0262(6) Uani 1 1 d . . . . .
C01C C -0.3180(3) 0.68301(16) 0.94648(16) 0.0285(6) Uani 1 1 d . . . . .
H01C H -0.386335 0.707983 0.917963 0.034 Uiso 1 1 calc R . . . .
C01D C -0.3612(3) 1.01500(17) 0.83041(16) 0.0299(6) Uani 1 1 d . . . . .
H01D H -0.395464 1.070905 0.833649 0.036 Uiso 1 1 calc R . . . .
C32 C 1.2273(3) 0.74701(16) 0.18450(14) 0.0236(5) Uani 1 1 d . . . . .
H32A H 1.167605 0.761410 0.229762 0.028 Uiso 1 1 calc R . . . .
H32B H 1.309074 0.768460 0.186813 0.028 Uiso 1 1 calc R . . . .
C01F C -0.1972(3) 0.75711(16) 0.80528(14) 0.0240(5) Uani 1 1 d . . . . .
H01A H -0.271876 0.730279 0.799989 0.029 Uiso 1 1 calc R . . . .
H01B H -0.136520 0.750403 0.759684 0.029 Uiso 1 1 calc R . . . .
C3 C 1.3890(3) 0.85958(18) -0.02147(16) 0.0290(6) Uani 1 1 d . . . . .
H3 H 1.480527 0.861244 -0.035920 0.035 Uiso 1 1 calc R . . . .
C01H C 0.4587(3) 0.82076(16) 0.49877(16) 0.0257(6) Uani 1 1 d . . . . .
H01H H 0.509801 0.803218 0.537541 0.031 Uiso 1 1 calc R . . . .
C11 C 0.8437(3) 0.86413(16) 0.03149(14) 0.0227(5) Uani 1 1 d . . . . .
H11A H 0.833055 0.823163 -0.002034 0.027 Uiso 1 1 calc R . . . .
H11B H 0.829282 0.916220 0.006302 0.027 Uiso 1 1 calc R . . . .
C5 C 1.1507(3) 0.89561(17) -0.04735(15) 0.0261(6) Uani 1 1 d . . . . .
H5 H 1.084424 0.920336 -0.077152 0.031 Uiso 1 1 calc R . . . .
C01K C 0.4452(3) 0.82771(16) 0.36931(16) 0.0284(6) Uani 1 1 d . . . . .
H01K H 0.485710 0.814358 0.321880 0.034 Uiso 1 1 calc R . . . .
C01L C 0.3115(3) 0.87256(16) 0.38139(15) 0.0271(6) Uani 1 1 d . . . . .
H01L H 0.262229 0.890510 0.342021 0.033 Uiso 1 1 calc R . . . .
C01M C -0.4401(3) 0.96510(18) 0.80649(15) 0.0289(6) Uani 1 1 d . . . . .
H01M H -0.528093 0.987555 0.794323 0.035 Uiso 1 1 calc R . . . .
C01N C 0.2568(3) 0.99553(15) 0.63372(15) 0.0250(6) Uani 1 1 d . . . . .
C38 C 1.2140(3) 0.61035(18) 0.13375(15) 0.0304(6) Uani 1 1 d . . . . .
H38 H 1.151739 0.637743 0.102899 0.036 Uiso 1 1 calc R . . . .
C27 C 1.1031(3) 0.57164(16) 0.39118(17) 0.0285(6) Uani 1 1 d . . . . .
H27 H 1.109927 0.515903 0.387604 0.034 Uiso 1 1 calc R . . . .
C01Q C 0.5180(3) 0.80285(16) 0.42823(17) 0.0291(6) Uani 1 1 d . . . . .
H01Q H 0.608605 0.773572 0.420077 0.035 Uiso 1 1 calc R . . . .
C01R C -0.2114(3) 0.84689(18) 0.61184(16) 0.0292(6) Uani 1 1 d . . . . .
H01R H -0.298625 0.835789 0.613218 0.035 Uiso 1 1 calc R . . . .
C18 C 0.9067(3) 0.41709(16) 0.37543(17) 0.0293(6) Uani 1 1 d . . . . .
H18A H 0.996672 0.420524 0.386323 0.044 Uiso 1 1 calc GR . . . .
H18B H 0.910968 0.364875 0.354623 0.044 Uiso 1 1 calc GR . . . .
H18C H 0.844094 0.423862 0.419654 0.044 Uiso 1 1 calc GR . . . .
C19 C 0.7215(3) 0.47058(17) 0.29723(16) 0.0296(6) Uani 1 1 d . . . . .
H19A H 0.652467 0.476774 0.338784 0.044 Uiso 1 1 calc GR . . . .
H19B H 0.736010 0.416693 0.277827 0.044 Uiso 1 1 calc GR . . . .
H19C H 0.691400 0.509772 0.260318 0.044 Uiso 1 1 calc GR . . . .
C10 C 0.7368(3) 0.86806(16) 0.09882(14) 0.0240(5) Uani 1 1 d . . . . .
H10A H 0.728676 0.918485 0.124779 0.029 Uiso 1 1 calc R . . . .
H10B H 0.647719 0.867555 0.083282 0.029 Uiso 1 1 calc R . . . .
C01V C -0.2306(3) 0.98097(18) 0.84954(16) 0.0299(6) Uani 1 1 d . . . . .
H01V H -0.177974 1.013977 0.866788 0.036 Uiso 1 1 calc R . . . .
C01W C -0.3495(3) 0.64479(18) 1.01202(16) 0.0324(6) Uani 1 1 d . . . . .
H01W H -0.441086 0.644557 1.027977 0.039 Uiso 1 1 calc R . . . .
C01X C 0.4126(3) 0.99165(18) 0.62532(17) 0.0315(6) Uani 1 1 d . . . . .
H01E H 0.456581 0.948773 0.655686 0.047 Uiso 1 1 calc GR . . . .
H01F H 0.429061 1.042596 0.639909 0.047 Uiso 1 1 calc GR . . . .
H01G H 0.449531 0.981140 0.575105 0.047 Uiso 1 1 calc GR . . . .
C4 C 1.2882(3) 0.89591(18) -0.06654(16) 0.0305(6) Uani 1 1 d . . . . .
H4 H 1.314600 0.920646 -0.110155 0.037 Uiso 1 1 calc R . . . .
C01Z C -0.1097(3) 0.60592(18) 1.03361(16) 0.0315(6) Uani 1 1 d . . . . .
H01Z H -0.042243 0.580298 1.062367 0.038 Uiso 1 1 calc R . . . .
C29 C 1.2074(3) 0.68251(17) 0.41449(17) 0.0293(6) Uani 1 1 d . . . . .
H29 H 1.282795 0.701677 0.425811 0.035 Uiso 1 1 calc R . . . .
C021 C -0.0967(3) 0.79151(18) 0.58035(16) 0.0302(6) Uani 1 1 d . . . . .
H021 H -0.106943 0.743518 0.560193 0.036 Uiso 1 1 calc R . . . .
C28 C 1.2154(3) 0.59992(18) 0.40910(19) 0.0344(7) Uani 1 1 d . . . . .
H28 H 1.296144 0.563163 0.417485 0.041 Uiso 1 1 calc R . . . .
C023 C 0.1890(3) 1.06056(17) 0.58152(19) 0.0363(7) Uani 1 1 d . . . . .
H02A H 0.228507 1.047190 0.532110 0.054 Uiso 1 1 calc GR . . . .
H02B H 0.204255 1.112579 0.593928 0.054 Uiso 1 1 calc GR . . . .
H02C H 0.091847 1.062658 0.585813 0.054 Uiso 1 1 calc GR . . . .
C024 C 0.1967(3) 0.63570(19) 0.95068(16) 0.0314(6) Uani 1 1 d . . . . .
H02D H 0.209961 0.584712 0.977646 0.038 Uiso 1 1 calc R . . . .
H02E H 0.210920 0.677530 0.982215 0.038 Uiso 1 1 calc R . . . .
C025 C 0.1986(3) 1.01797(19) 0.71352(18) 0.0355(7) Uani 1 1 d . . . . .
H02F H 0.100742 1.022316 0.719314 0.053 Uiso 1 1 calc GR . . . .
H02G H 0.218215 1.069104 0.725219 0.053 Uiso 1 1 calc GR . . . .
H02H H 0.240572 0.976484 0.745757 0.053 Uiso 1 1 calc GR . . . .
C026 C 0.3004(3) 0.62768(18) 0.88336(16) 0.0312(6) Uani 1 1 d . . . . .
H02I H 0.390551 0.627944 0.897577 0.037 Uiso 1 1 calc R . . . .
H02J H 0.305842 0.576171 0.859713 0.037 Uiso 1 1 calc R . . . .
C17 C 0.9626(3) 0.47929(18) 0.25245(17) 0.0325(6) Uani 1 1 d . . . . .
H17A H 0.929649 0.521317 0.218408 0.049 Uiso 1 1 calc GR . . . .
H17B H 0.976104 0.427103 0.229778 0.049 Uiso 1 1 calc GR . . . .
H17C H 1.048463 0.486476 0.266623 0.049 Uiso 1 1 calc GR . . . .
C028 C -0.2468(3) 0.60645(19) 1.05492(17) 0.0350(7) Uani 1 1 d . . . . .
H028 H -0.271449 0.580963 1.098433 0.042 Uiso 1 1 calc R . . . .
C37 C 1.2488(3) 0.52545(18) 0.13261(17) 0.0340(7) Uani 1 1 d . . . . .
H37 H 1.212418 0.496691 0.100349 0.041 Uiso 1 1 calc R . . . .
C36 C 1.3379(3) 0.48474(19) 0.17993(19) 0.0379(7) Uani 1 1 d . . . . .
H36 H 1.362399 0.428192 0.179783 0.045 Uiso 1 1 calc R . . . .
C34 C 1.3578(3) 0.6130(2) 0.2272(2) 0.0426(8) Uani 1 1 d . . . . .
H34 H 1.395283 0.641463 0.259137 0.051 Uiso 1 1 calc R . . . .
C35 C 1.3904(4) 0.5285(2) 0.2274(2) 0.0485(9) Uani 1 1 d . . . . .
H35 H 1.448696 0.500974 0.260142 0.058 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si1 C26 1.879(3) . ?
Si1 C15 1.878(3) . ?
Si1 C20 1.888(3) . ?
Si1 C16 1.907(3) . ?
Si02 C00K 1.879(3) . ?
Si02 C00T 1.879(3) . ?
Si02 C00W 1.877(3) . ?
Si02 C01N 1.900(3) . ?
O003 C12 1.218(3) . ?
O004 C00N 1.228(3) . ?
N1 C9 1.420(3) . ?
N1 C12 1.369(3) . ?
N1 C10 1.458(3) . ?
N006 C00H 1.394(3) . ?
N006 C010 1.382(3) . ?
N006 C01F 1.463(3) . ?
N2 C1 1.381(3) . ?
N2 C8 1.394(3) . ?
N2 C32 1.460(3) . ?
N008 C00M 1.426(3) . ?
N008 C00N 1.361(3) . ?
N008 C026 1.463(3) . ?
C9 C8 1.435(4) . ?
C9 C14 1.354(4) . ?
C7 C8 1.375(4) . ?
C7 C6 1.422(4) . ?
C7 C11 1.500(4) . ?
C12 C13 1.514(3) . ?
C26 C31 1.395(4) . ?
C26 C27 1.394(4) . ?
C1 C2 1.401(4) . ?
C1 C6 1.417(4) . ?
C31 C30 1.377(4) . ?
C13 C15 1.350(4) . ?
C13 C14 1.449(4) . ?
C00H C00M 1.433(4) . ?
C00H C00V 1.375(4) . ?
C00J C00N 1.508(3) . ?
C00J C00S 1.454(4) . ?
C00J C00T 1.335(4) . ?
C00K C011 1.402(4) . ?
C00K C016 1.401(4) . ?
C20 C21 1.398(4) . ?
C20 C25 1.397(4) . ?
C00M C00S 1.353(4) . ?
C00O C00U 1.389(4) . ?
C00O C017 1.397(4) . ?
C00O C01F 1.518(4) . ?
C2 C3 1.377(4) . ?
C00Q C00W 1.400(4) . ?
C00Q C01L 1.395(4) . ?
C6 C5 1.410(4) . ?
C00U C01M 1.388(4) . ?
C00V C01B 1.423(4) . ?
C00V C024 1.501(4) . ?
C00W C01H 1.408(4) . ?
C21 C22 1.399(4) . ?
C22 C23 1.379(4) . ?
C010 C01B 1.419(4) . ?
C010 C01C 1.393(4) . ?
C011 C019 1.385(4) . ?
C16 C18 1.531(4) . ?
C16 C19 1.528(4) . ?
C16 C17 1.541(4) . ?
C25 C24 1.384(4) . ?
C30 C29 1.381(4) . ?
C33 C32 1.519(4) . ?
C33 C38 1.386(4) . ?
C33 C34 1.382(4) . ?
C016 C021 1.377(4) . ?
C017 C01V 1.389(4) . ?
C24 C23 1.386(4) . ?
C019 C01R 1.377(4) . ?
C01B C01Z 1.407(4) . ?
C01C C01W 1.385(4) . ?
C01D C01M 1.385(4) . ?
C01D C01V 1.390(4) . ?
C3 C4 1.406(4) . ?
C01H C01Q 1.375(4) . ?
C11 C10 1.532(4) . ?
C5 C4 1.382(4) . ?
C01K C01L 1.382(4) . ?
C01K C01Q 1.381(4) . ?
C01N C01X 1.537(4) . ?
C01N C023 1.532(4) . ?
C01N C025 1.540(4) . ?
C38 C37 1.396(4) . ?
C27 C28 1.390(4) . ?
C01R C021 1.390(4) . ?
C01W C028 1.402(4) . ?
C01Z C028 1.381(4) . ?
C29 C28 1.382(4) . ?
C024 C026 1.508(4) . ?
C37 C36 1.380(4) . ?
C36 C35 1.378(5) . ?
C34 C35 1.388(5) . ?

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
C26 Si1 C20 105.72(11) . . ?
C26 Si1 C16 113.91(12) . . ?
C15 Si1 C26 109.99(11) . . ?
C15 Si1 C20 107.24(11) . . ?
C15 Si1 C16 107.02(12) . . ?
C20 Si1 C16 112.81(12) . . ?
C00K Si02 C00T 109.43(11) . . ?
C00K Si02 C01N 115.82(12) . . ?
C00T Si02 C01N 106.85(11) . . ?
C00W Si02 C00K 106.61(11) . . ?
C00W Si02 C00T 108.89(11) . . ?
C00W Si02 C01N 109.11(12) . . ?
C9 N1 C10 123.3(2) . . ?
C12 N1 C9 110.5(2) . . ?
C12 N1 C10 125.5(2) . . ?
C00H N006 C01F 128.4(2) . . ?
C010 N006 C00H 107.7(2) . . ?
C010 N006 C01F 123.9(2) . . ?
C1 N2 C8 107.2(2) . . ?
C1 N2 C32 125.4(2) . . ?
C8 N2 C32 127.4(2) . . ?
C00M N008 C026 123.7(2) . . ?
C00N N008 C00M 110.4(2) . . ?
C00N N008 C026 124.7(2) . . ?
N1 C9 C8 114.6(2) . . ?
C14 C9 N1 110.0(2) . . ?
C14 C9 C8 135.2(2) . . ?
C8 C7 C6 106.8(2) . . ?
C8 C7 C11 122.1(2) . . ?
C6 C7 C11 131.0(2) . . ?
O003 C12 N1 125.9(2) . . ?
O003 C12 C13 128.7(2) . . ?
N1 C12 C13 105.5(2) . . ?
C31 C26 Si1 119.31(19) . . ?
C31 C26 C27 117.1(2) . . ?
C27 C26 Si1 123.3(2) . . ?
N2 C1 C2 129.2(2) . . ?
N2 C1 C6 108.6(2) . . ?
C2 C1 C6 122.2(2) . . ?
C30 C31 C26 121.7(2) . . ?
C15 C13 C12 123.4(2) . . ?
C15 C13 C14 130.8(2) . . ?
C14 C13 C12 105.7(2) . . ?
C13 C15 Si1 127.82(19) . . ?
N006 C00H C00M 127.5(2) . . ?
C00V C00H N006 109.9(2) . . ?
C00V C00H C00M 122.6(2) . . ?
N2 C8 C9 127.1(2) . . ?
C7 C8 N2 110.4(2) . . ?
C7 C8 C9 122.3(2) . . ?
C00S C00J C00N 104.9(2) . . ?
C00T C00J C00N 122.2(2) . . ?
C00T C00J C00S 132.8(2) . . ?
C011 C00K Si02 125.7(2) . . ?
C011 C00K C016 117.2(2) . . ?
C016 C00K Si02 117.0(2) . . ?
C21 C20 Si1 119.44(19) . . ?
C25 C20 Si1 123.6(2) . . ?
C25 C20 C21 116.9(2) . . ?
N008 C00M C00H 114.4(2) . . ?
C00S C00M N008 109.3(2) . . ?
C00S C00M C00H 136.3(2) . . ?
O004 C00N N008 126.2(2) . . ?
O004 C00N C00J 127.4(2) . . ?
N008 C00N C00J 106.3(2) . . ?
C00U C00O C017 118.8(2) . . ?
C00U C00O C01F 120.2(2) . . ?
C017 C00O C01F 121.0(2) . . ?
C3 C2 C1 117.0(3) . . ?
C01L C00Q C00W 121.7(2) . . ?
C1 C6 C7 107.0(2) . . ?
C5 C6 C7 133.8(2) . . ?
C5 C6 C1 119.2(2) . . ?
C00M C00S C00J 109.0(2) . . ?
C00J C00T Si02 128.6(2) . . ?
C00O C00U C01M 120.6(3) . . ?
C00H C00V C01B 107.2(2) . . ?
C00H C00V C024 121.7(3) . . ?
C01B C00V C024 131.0(3) . . ?
C00Q C00W Si02 119.81(19) . . ?
C00Q C00W C01H 116.8(2) . . ?
C01H C00W Si02 123.4(2) . . ?
C22 C21 C20 121.8(2) . . ?
C9 C14 C13 108.3(2) . . ?
C23 C22 C21 119.7(2) . . ?
N006 C010 C01B 108.4(2) . . ?
N006 C010 C01C 129.2(3) . . ?
C01C C010 C01B 122.4(3) . . ?
C019 C011 C00K 121.2(3) . . ?
C18 C16 Si1 112.77(19) . . ?
C18 C16 C17 110.2(2) . . ?
C19 C16 Si1 107.90(18) . . ?
C19 C16 C18 108.2(2) . . ?
C19 C16 C17 108.6(2) . . ?
C17 C16 Si1 109.10(18) . . ?
C24 C25 C20 121.6(2) . . ?
C31 C30 C29 120.4(2) . . ?
C38 C33 C32 122.3(2) . . ?
C34 C33 C32 119.2(3) . . ?
C34 C33 C38 118.2(3) . . ?
C021 C016 C00K 121.8(3) . . ?
C01V C017 C00O 120.6(2) . . ?
C25 C24 C23 120.5(2) . . ?
C01R C019 C011 120.2(3) . . ?
C22 C23 C24 119.5(3) . . ?
C010 C01B C00V 106.9(2) . . ?
C01Z C01B C00V 134.4(3) . . ?
C01Z C01B C010 118.7(3) . . ?
C01W C01C C010 117.1(3) . . ?
C01M C01D C01V 119.6(3) . . ?
N2 C32 C33 114.6(2) . . ?
N006 C01F C00O 114.3(2) . . ?
C2 C3 C4 121.9(3) . . ?
C01Q C01H C00W 121.3(3) . . ?
C7 C11 C10 110.0(2) . . ?
C4 C5 C6 118.3(3) . . ?
C01Q C01K C01L 119.5(3) . . ?
C01K C01L C00Q 119.8(3) . . ?
C01D C01M C00U 120.4(3) . . ?
C01X C01N Si02 106.53(18) . . ?
C01X C01N C025 108.4(2) . . ?
C023 C01N Si02 110.58(18) . . ?
C023 C01N C01X 109.0(2) . . ?
C023 C01N C025 110.1(2) . . ?
C025 C01N Si02 112.13(19) . . ?
C33 C38 C37 121.7(3) . . ?
C28 C27 C26 121.4(3) . . ?
C01H C01Q C01K 121.0(3) . . ?
C019 C01R C021 119.9(3) . . ?
N1 C10 C11 110.9(2) . . ?
C017 C01V C01D 120.0(3) . . ?
C01C C01W C028 121.7(3) . . ?
C5 C4 C3 121.3(3) . . ?
C028 C01Z C01B 118.9(3) . . ?
C30 C29 C28 119.2(2) . . ?
C016 C021 C01R 119.7(3) . . ?
C29 C28 C27 120.1(3) . . ?
C00V C024 C026 110.7(2) . . ?
N008 C026 C024 111.1(2) . . ?
C01Z C028 C01W 121.1(3) . . ?
C36 C37 C38 119.2(3) . . ?
C35 C36 C37 119.5(3) . . ?
C33 C34 C35 120.3(3) . . ?
C36 C35 C34 121.1(3) . . ?

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

data_exp_1421
_database_code_depnum_ccdc_archive 'CCDC 1880232'
loop_
_audit_author_name
_audit_author_address
'Yongxiang Liu'
;Shenyang Pharmaceutical University
China
;
_audit_update_record             
;
2019-04-16 deposited with the CCDC.	2019-10-18 downloaded from the CCDC.
;
_audit_creation_date             2018-04-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H22 N2 O3'
_chemical_formula_sum            'C21 H22 N2 O3'
_chemical_formula_weight         350.40
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   17.426(2)
_cell_length_b                   7.9081(7)
_cell_length_c                   14.0205(16)
_cell_angle_alpha                90
_cell_angle_beta                 106.829(13)
_cell_angle_gamma                90
_cell_volume                     1849.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3809
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      26.5490
_cell_measurement_theta_min      2.8430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61515
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_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  0.0498
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11542
_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         2.442
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(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    -84.00  13.00   1.00    3.00    --  -11.74 -57.00 120.00   97
  2  ω    -79.00  20.00   1.00    3.00    --  -11.74 -77.00   0.00   99
  3  ω    -40.00  58.00   1.00    3.00    --  -11.74  57.00 -90.00   98
;
_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      0.0221385000
_diffrn_orient_matrix_UB_12      0.0164705000
_diffrn_orient_matrix_UB_13      -0.0343344000
_diffrn_orient_matrix_UB_21      0.0362828000
_diffrn_orient_matrix_UB_22      -0.0044994000
_diffrn_orient_matrix_UB_23      0.0392847000
_diffrn_orient_matrix_UB_31      0.0022080000
_diffrn_orient_matrix_UB_32      -0.0879477000
_diffrn_orient_matrix_UB_33      -0.0083840000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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                2740
_reflns_number_total             3258
_reflns_odcompleteness_completeness 99.93
_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 (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         0.692
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0954
_refine_ls_R_factor_gt           0.0835
_refine_ls_restrained_S_all      1.057
_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)+(0.1180P)²+2.4891P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2124
_refine_ls_wR_factor_ref         0.2233
_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:
 C10(H10A,H10B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C5(H5), C14(H14), C2(H2), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O2 O 0.74499(12) 0.3270(2) 0.52246(15) 0.0259(5) Uani 1 1 d . . . . .
O1 O 0.67779(15) 0.3537(3) 0.35835(16) 0.0349(6) Uani 1 1 d . . . . .
N1 N 0.66423(14) 0.5491(3) 0.47229(17) 0.0210(6) Uani 1 1 d . . . . .
N2 N 0.77781(16) 0.7138(3) 0.72392(18) 0.0284(6) Uani 1 1 d . . . . .
O3 O 0.85551(18) 0.7967(4) 0.87767(19) 0.0610(9) Uani 1 1 d . . . . .
C11 C 0.77108(18) 0.6513(3) 0.6289(2) 0.0221(7) Uani 1 1 d . . . . .
C17 C 0.69611(16) 0.4004(4) 0.4435(2) 0.0214(6) Uani 1 1 d . . . . .
C7 C 0.68882(17) 0.6286(3) 0.5669(2) 0.0212(6) Uani 1 1 d . . . . .
C6 C 0.58287(17) 0.5948(4) 0.4280(2) 0.0235(7) Uani 1 1 d . . . . .
C8 C 0.62619(19) 0.7183(4) 0.5816(2) 0.0268(7) Uani 1 1 d . . . . .
C12 C 0.83773(18) 0.6356(4) 0.5975(2) 0.0230(7) Uani 1 1 d . . . . .
H12 H 0.832866 0.598231 0.533085 0.028 Uiso 1 1 calc R . . . .
C1 C 0.55880(18) 0.6990(4) 0.4943(2) 0.0274(7) Uani 1 1 d . . . . .
C5 C 0.53071(18) 0.5464(4) 0.3367(2) 0.0289(7) Uani 1 1 d . . . . .
H5 H 0.546733 0.473845 0.293862 0.035 Uiso 1 1 calc R . . . .
C13 C 0.91437(19) 0.6758(4) 0.6621(2) 0.0302(7) Uani 1 1 d . . . . .
C14 C 0.9200(2) 0.7280(4) 0.7567(2) 0.0357(8) Uani 1 1 d . . . . .
H14 H 0.970514 0.751938 0.799500 0.043 Uiso 1 1 calc R . . . .
C15 C 0.8519(2) 0.7476(5) 0.7930(2) 0.0379(9) Uani 1 1 d . . . . .
C2 C 0.4796(2) 0.7596(4) 0.4674(3) 0.0365(9) Uani 1 1 d . . . . .
H2 H 0.462130 0.827462 0.511109 0.044 Uiso 1 1 calc R . . . .
C18 C 0.7900(2) 0.1719(4) 0.5121(3) 0.0343(8) Uani 1 1 d . . . . .
C10 C 0.7043(2) 0.7359(5) 0.7560(3) 0.0372(8) Uani 1 1 d . . . . .
H10A H 0.716415 0.807440 0.814683 0.045 Uiso 1 1 calc R . . . .
H10B H 0.687197 0.626672 0.773899 0.045 Uiso 1 1 calc R . . . .
C9 C 0.6373(2) 0.8138(4) 0.6754(3) 0.0362(8) Uani 1 1 d . . . . .
H9A H 0.588110 0.811291 0.694686 0.043 Uiso 1 1 calc R . . . .
H9B H 0.649861 0.930863 0.665674 0.043 Uiso 1 1 calc R . . . .
C4 C 0.45352(19) 0.6119(5) 0.3128(3) 0.0382(9) Uani 1 1 d . . . . .
H4 H 0.417297 0.583417 0.251992 0.046 Uiso 1 1 calc R . . . .
C16 C 0.9859(2) 0.6619(5) 0.6239(3) 0.0413(9) Uani 1 1 d . . . . .
H16A H 0.998084 0.544837 0.617474 0.062 Uiso 1 1 calc GR . . . .
H16B H 1.031020 0.716149 0.669700 0.062 Uiso 1 1 calc GR . . . .
H16C H 0.974555 0.715964 0.559996 0.062 Uiso 1 1 calc GR . . . .
C3 C 0.4287(2) 0.7184(5) 0.3767(3) 0.0413(9) Uani 1 1 d . . . . .
H3 H 0.376876 0.761977 0.357502 0.050 Uiso 1 1 calc R . . . .
C19 C 0.7309(2) 0.0300(4) 0.4765(3) 0.0443(9) Uani 1 1 d . . . . .
H19A H 0.699746 0.015269 0.522290 0.066 Uiso 1 1 calc GR . . . .
H19B H 0.759304 -0.072605 0.472833 0.066 Uiso 1 1 calc GR . . . .
H19C H 0.695933 0.057077 0.411714 0.066 Uiso 1 1 calc GR . . . .
C20 C 0.8386(3) 0.1411(5) 0.6200(3) 0.0627(14) Uani 1 1 d . . . . .
H20A H 0.872565 0.236770 0.644186 0.094 Uiso 1 1 calc GR . . . .
H20B H 0.870952 0.041729 0.623704 0.094 Uiso 1 1 calc GR . . . .
H20C H 0.802844 0.125448 0.660081 0.094 Uiso 1 1 calc GR . . . .
C21 C 0.8418(3) 0.2070(6) 0.4448(5) 0.0764(17) Uani 1 1 d . . . . .
H21A H 0.808273 0.226881 0.378245 0.115 Uiso 1 1 calc GR . . . .
H21B H 0.875757 0.111331 0.445061 0.115 Uiso 1 1 calc GR . . . .
H21C H 0.874227 0.304982 0.468349 0.115 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
O2 C17 1.320(4) . ?
O2 C18 1.485(4) . ?
O1 C17 1.201(4) . ?
N1 C17 1.409(4) . ?
N1 C7 1.417(4) . ?
N1 C6 1.420(4) . ?
N2 C11 1.394(4) . ?
N2 C15 1.397(4) . ?
N2 C10 1.486(4) . ?
O3 C15 1.233(4) . ?
C11 C7 1.457(4) . ?
C11 C12 1.362(4) . ?
C7 C8 1.367(4) . ?
C6 C1 1.395(4) . ?
C6 C5 1.392(4) . ?
C8 C1 1.438(5) . ?
C8 C9 1.480(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.416(4) . ?
C1 C2 1.405(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.389(5) . ?
C13 C14 1.365(5) . ?
C13 C16 1.497(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.429(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.363(6) . ?
C18 C19 1.507(5) . ?
C18 C20 1.524(5) . ?
C18 C21 1.508(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C9 1.502(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C4 H4 0.9300 . ?
C4 C3 1.387(6) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C3 H3 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
C17 O2 C18 120.8(2) . . ?
C17 N1 C7 127.0(2) . . ?
C17 N1 C6 120.9(2) . . ?
C7 N1 C6 106.8(2) . . ?
C11 N2 C15 122.4(3) . . ?
C11 N2 C10 119.3(3) . . ?
C15 N2 C10 118.2(3) . . ?
N2 C11 C7 114.2(3) . . ?
C12 C11 N2 119.9(3) . . ?
C12 C11 C7 125.4(3) . . ?
O2 C17 N1 109.8(2) . . ?
O1 C17 O2 128.3(3) . . ?
O1 C17 N1 121.9(3) . . ?
N1 C7 C11 126.3(2) . . ?
C8 C7 N1 109.5(3) . . ?
C8 C7 C11 122.4(3) . . ?
C1 C6 N1 108.3(3) . . ?
C5 C6 N1 129.5(3) . . ?
C5 C6 C1 122.2(3) . . ?
C7 C8 C1 107.9(3) . . ?
C7 C8 C9 119.7(3) . . ?
C1 C8 C9 132.4(3) . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.5(3) . . ?
C13 C12 H12 119.8 . . ?
C6 C1 C8 107.5(3) . . ?
C6 C1 C2 118.9(3) . . ?
C2 C1 C8 133.5(3) . . ?
C6 C5 H5 121.7 . . ?
C4 C5 C6 116.6(3) . . ?
C4 C5 H5 121.7 . . ?
C12 C13 C16 118.9(3) . . ?
C14 C13 C12 118.6(3) . . ?
C14 C13 C16 122.5(3) . . ?
C13 C14 H14 118.5 . . ?
C13 C14 C15 123.0(3) . . ?
C15 C14 H14 118.5 . . ?
N2 C15 C14 115.4(3) . . ?
O3 C15 N2 120.5(3) . . ?
O3 C15 C14 124.1(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2 120.2 . . ?
O2 C18 C19 108.5(3) . . ?
O2 C18 C20 101.1(3) . . ?
O2 C18 C21 109.7(3) . . ?
C19 C18 C20 109.9(3) . . ?
C21 C18 C19 113.9(4) . . ?
C21 C18 C20 112.9(4) . . ?
N2 C10 H10A 109.3 . . ?
N2 C10 H10B 109.3 . . ?
N2 C10 C9 111.8(3) . . ?
H10A C10 H10B 107.9 . . ?
C9 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C8 C9 C10 109.4(3) . . ?
C8 C9 H9A 109.8 . . ?
C8 C9 H9B 109.8 . . ?
C10 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
C5 C4 H4 118.9 . . ?
C3 C4 C5 122.2(3) . . ?
C3 C4 H4 118.9 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 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
N1 C7 C8 C1 -0.5(3) . . . . ?
N1 C7 C8 C9 -179.7(3) . . . . ?
N1 C6 C1 C8 -0.1(3) . . . . ?
N1 C6 C1 C2 -179.3(3) . . . . ?
N1 C6 C5 C4 179.9(3) . . . . ?
N2 C11 C7 N1 -172.1(2) . . . . ?
N2 C11 C7 C8 24.7(4) . . . . ?
N2 C11 C12 C13 2.7(4) . . . . ?
N2 C10 C9 C8 51.1(4) . . . . ?
C11 N2 C15 O3 -177.2(3) . . . . ?
C11 N2 C15 C14 5.4(5) . . . . ?
C11 N2 C10 C9 -43.5(4) . . . . ?
C11 C7 C8 C1 165.2(3) . . . . ?
C11 C7 C8 C9 -13.9(4) . . . . ?
C11 C12 C13 C14 0.9(5) . . . . ?
C11 C12 C13 C16 -178.2(3) . . . . ?
C17 O2 C18 C19 -66.4(4) . . . . ?
C17 O2 C18 C20 178.1(3) . . . . ?
C17 O2 C18 C21 58.6(4) . . . . ?
C17 N1 C7 C11 41.3(4) . . . . ?
C17 N1 C7 C8 -153.6(3) . . . . ?
C17 N1 C6 C1 155.8(2) . . . . ?
C17 N1 C6 C5 -22.2(4) . . . . ?
C7 N1 C17 O2 10.1(4) . . . . ?
C7 N1 C17 O1 -171.0(3) . . . . ?
C7 N1 C6 C1 -0.2(3) . . . . ?
C7 N1 C6 C5 -178.2(3) . . . . ?
C7 C11 C12 C13 174.2(3) . . . . ?
C7 C8 C1 C6 0.4(3) . . . . ?
C7 C8 C1 C2 179.4(3) . . . . ?
C7 C8 C9 C10 -24.7(4) . . . . ?
C6 N1 C17 O2 -140.7(2) . . . . ?
C6 N1 C17 O1 38.2(4) . . . . ?
C6 N1 C7 C11 -164.6(3) . . . . ?
C6 N1 C7 C8 0.4(3) . . . . ?
C6 C1 C2 C3 -1.2(4) . . . . ?
C6 C5 C4 C3 -0.9(5) . . . . ?
C8 C1 C2 C3 179.8(3) . . . . ?
C12 C11 C7 N1 16.0(4) . . . . ?
C12 C11 C7 C8 -147.2(3) . . . . ?
C12 C13 C14 C15 -1.4(5) . . . . ?
C1 C6 C5 C4 2.2(4) . . . . ?
C1 C8 C9 C10 156.4(3) . . . . ?
C1 C2 C3 C4 2.6(5) . . . . ?
C5 C6 C1 C8 178.0(3) . . . . ?
C5 C6 C1 C2 -1.2(4) . . . . ?
C5 C4 C3 C2 -1.5(5) . . . . ?
C13 C14 C15 N2 -1.7(5) . . . . ?
C13 C14 C15 O3 -179.0(4) . . . . ?
C15 N2 C11 C7 -178.4(3) . . . . ?
C15 N2 C11 C12 -6.0(4) . . . . ?
C15 N2 C10 C9 140.2(3) . . . . ?
C18 O2 C17 O1 4.3(5) . . . . ?
C18 O2 C17 N1 -176.9(2) . . . . ?
C10 N2 C11 C7 5.5(4) . . . . ?
C10 N2 C11 C12 177.9(3) . . . . ?
C10 N2 C15 O3 -1.1(5) . . . . ?
C10 N2 C15 C14 -178.5(3) . . . . ?
C9 C8 C1 C6 179.4(3) . . . . ?
C9 C8 C1 C2 -1.6(6) . . . . ?
C16 C13 C14 C15 177.7(3) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.601
_oxdiff_exptl_absorpt_empirical_full_min 0.740
