# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1245
_database_code_depnum_ccdc_archive 'CCDC 1853111'
_audit_update_record             
;
2018-07-03 deposited with the CCDC.
2018-09-07 downloaded from the CCDC.
;
_audit_creation_date             2017-10-14
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C25 H25 N O5'
_chemical_formula_sum            'C25 H25 N O5'
_chemical_formula_weight         419.48
_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 0.00347 0.00161 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 0.01158 0.00611 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'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'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                   8.1390(5)
_cell_length_b                   15.8253(10)
_cell_length_c                   17.1850(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2213.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3085
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.3520
_cell_measurement_theta_min      3.7770
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93555
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.2587
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888.4862
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_ambient_temperature      293(2)
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13669
_diffrn_reflns_theta_full        28.8656
_diffrn_reflns_theta_max         28.87
_diffrn_reflns_theta_min         3.45
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0851
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 0.8671
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     32.00  98.00   1.00    3.20    --   19.44-178.00 -60.00   66
  2  ω    -25.00  63.00   1.00    3.20    --   19.44 -99.00  30.00   88
  3  ω    -12.00  90.00   1.00    3.20    --   19.44  76.00  43.00  102
  4  ω     -2.00  69.00   1.00    3.20    --   19.44  57.00-180.00   71
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0391333000
_diffrn_orient_matrix_UB_12      -0.0349301000
_diffrn_orient_matrix_UB_13      0.0180727000
_diffrn_orient_matrix_UB_21      0.0314727000
_diffrn_orient_matrix_UB_22      0.0129987000
_diffrn_orient_matrix_UB_23      0.0365910000
_diffrn_orient_matrix_UB_31      -0.0711825000
_diffrn_orient_matrix_UB_32      0.0249067000
_diffrn_orient_matrix_UB_33      0.0062339000
_diffrn_oxdiff_ac3_digest_frames 
;
01bd8ae0544bc4d94d08e5a8bc9ac5e31f000283e30
;
_diffrn_oxdiff_ac3_digest_hkl    
;
011de6b872b189be47517514443d279e35b0c8
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.829
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              21
_reflns_limit_k_min              -20
_reflns_limit_l_max              22
_reflns_limit_l_min              -21
_reflns_number_gt                3103
_reflns_number_total             5032
_reflns_odcompleteness_completeness 99.50
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.2841
_refine_diff_density_min         -0.2988
_refine_diff_density_rms         0.0724
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   1(10)
_refine_ls_d_res_high            0.7361
_refine_ls_d_res_low             5.9090
_refine_ls_goodness_of_fit_ref   0.9863
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    44
_refine_ls_number_parameters     281
_refine_ls_number_reflns         5032
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0546
_refine_ls_restrained_S_all      0.9863
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0371P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0947
_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:
 C13(H13), C20(H20), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17a,H17b), C14(H14a,H14b), C16(H16a,H16b), C15(H15a,H15b)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C27(H27), C31(H31), C10(H10), C6(H6), C28(H28), C5(H5), C8(H8),
 C9(H9), C29(H29), C30(H30)
2.d Idealised Me refined as rotating group:
 C24(H24a,H24b,H24c)
;
_atom_sites_solution_primary     direct
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
O11 O -0.25097(16) -0.91589(8) -0.04764(8) 0.0456(4) Uani 1.000000 .
O21 O -0.75246(17) -0.99072(9) -0.23065(9) 0.0579(4) Uani 1.000000 .
O25 O -0.63631(18) -0.87709(10) -0.12433(10) 0.0662(5) Uani 1.000000 .
O18 O -0.39506(15) -0.86774(8) -0.18798(8) 0.0437(4) Uani 1.000000 .
C13 C -0.3303(2) -0.80526(11) -0.13408(12) 0.0371(5) Uani 1.000000 .
H13 H -0.4175(2) -0.78675(11) -0.09863(12) 0.0445(6) Uiso 1.000000 R
C17 C -0.1239(3) -0.77641(11) -0.03288(13) 0.0462(6) Uani 1.000000 .
H17a H -0.2095(3) -0.75959(11) 0.00321(13) 0.0555(7) Uiso 1.000000 R
H17b H -0.0342(3) -0.80040(11) -0.00299(13) 0.0555(7) Uiso 1.000000 R
C19 C -0.5467(2) -0.89731(12) -0.17589(13) 0.0407(5) Uani 1.000000 .
C2 C -0.2101(3) -1.04762(13) 0.01362(13) 0.0468(6) Uani 1.000000 .
C14 C -0.2689(3) -0.73051(12) -0.18119(13) 0.0534(6) Uani 1.000000 .
H14a H -0.1852(3) -0.74929(12) -0.21746(13) 0.0640(7) Uiso 1.000000 R
H14b H -0.3590(3) -0.70669(12) -0.21094(13) 0.0640(7) Uiso 1.000000 R
C26 C -0.4769(2) -1.03596(12) -0.24071(14) 0.0423(5) Uani 1.000000 .
C3 C -0.1408(3) -0.97574(13) -0.02418(13) 0.0444(5) Uani 1.000000 .
C20 C -0.5871(2) -0.95982(12) -0.23978(13) 0.0427(5) Uani 1.000000 .
H20 H -0.5785(2) -0.93104(12) -0.29010(13) 0.0512(6) Uiso 1.000000 R
C12 C -0.1908(2) -0.84251(11) -0.08807(12) 0.0385(5) Uani 1.000000 .
H12 H -0.1035(2) -0.85976(11) -0.12396(12) 0.0462(6) Uiso 1.000000 R
C4 C 0.0269(3) -0.97082(14) -0.03448(15) 0.0559(6) Uani 1.000000 .
H4 H 0.0721(3) -0.92413(14) -0.05939(15) 0.0671(7) Uiso 1.000000 R
N1 N -0.3761(2) -1.05100(11) 0.02271(11) 0.0578(5) Uani 1.000000 .
C27 C -0.4212(3) -1.06651(15) -0.31131(15) 0.0578(6) Uani 1.000000 .
H27 H -0.4488(3) -1.03872(15) -0.35718(15) 0.0694(8) Uiso 1.000000 R
C7 C -0.1043(3) -1.11255(14) 0.03906(15) 0.0621(7) Uani 1.000000 .
C16 C -0.0632(3) -0.69960(13) -0.07663(14) 0.0590(7) Uani 1.000000 .
H16a H -0.0273(3) -0.65696(13) -0.03983(14) 0.0708(8) Uiso 1.000000 R
H16b H 0.0302(3) -0.71518(13) -0.10864(14) 0.0708(8) Uiso 1.000000 R
C22 C -0.8737(3) -0.93939(18) -0.25764(18) 0.0715(8) Uani 1.000000 .
C15 C -0.1979(3) -0.66348(13) -0.12776(15) 0.0618(7) Uani 1.000000 .
H15a H -0.1536(3) -0.61764(13) -0.15880(15) 0.0742(8) Uiso 1.000000 R
H15b H -0.2846(3) -0.64067(13) -0.09522(15) 0.0742(8) Uiso 1.000000 R
O23 O -0.8471(2) -0.87116(13) -0.28294(16) 0.1129(9) Uani 1.000000 .
C31 C -0.4351(3) -1.07663(14) -0.17292(16) 0.0619(7) Uani 1.000000 .
H31 H -0.4722(3) -1.05605(14) -0.12536(16) 0.0743(8) Uiso 1.000000 R
C10 C -0.4346(4) -1.11901(18) 0.05637(17) 0.0817(9) Uani 1.000000 .
H10 H -0.5480(4) -1.12266(18) 0.06187(17) 0.0980(10) Uiso 1.000000 R
C6 C 0.0672(3) -1.10462(16) 0.02796(17) 0.0772(8) Uani 1.000000 .
H6 H 0.1373(3) -1.14706(16) 0.04527(17) 0.0926(10) Uiso 1.000000 R
C28 C -0.3259(3) -1.1373(2) -0.3138(2) 0.0822(9) Uani 1.000000 .
H28 H -0.2892(3) -1.1576(2) -0.3615(2) 0.0987(11) Uiso 1.000000 R
C5 C 0.1297(3) -1.03563(17) -0.00770(17) 0.0740(8) Uani 1.000000 .
H5 H 0.2427(3) -1.03109(17) -0.01458(17) 0.0888(9) Uiso 1.000000 R
C8 C -0.1772(4) -1.18257(17) 0.07600(18) 0.0851(9) Uani 1.000000 .
H8 H -0.1116(4) -1.22632(17) 0.09446(18) 0.1021(11) Uiso 1.000000 R
C9 C -0.3414(5) -1.18649(18) 0.08471(19) 0.0914(10) Uani 1.000000 .
H9 H -0.3910(5) -1.23252(18) 0.10876(19) 0.1097(12) Uiso 1.000000 R
C29 C -0.2839(3) -1.17870(16) -0.2474(3) 0.0900(10) Uani 1.000000 .
H29 H -0.2193(3) -1.22711(16) -0.2499(3) 0.1080(12) Uiso 1.000000 R
C30 C -0.3374(3) -1.14860(16) -0.1755(2) 0.0795(9) Uani 1.000000 .
H30 H -0.3081(3) -1.17633(16) -0.1299(2) 0.0955(10) Uiso 1.000000 R
C24 C -1.0361(3) -0.98238(19) -0.2513(2) 0.1002(11) Uani 1.000000 .
H24a H -1.0370(10) -1.0180(11) -0.2061(8) 0.1502(17) Uiso 1.000000 GR
H24b H -1.1214(4) -0.94072(19) -0.2468(14) 0.1502(17) Uiso 1.000000 GR
H24c H -1.0547(13) -1.0161(12) -0.2970(6) 0.1502(17) 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
O11 C3 1.365(2) . ?
O11 C12 1.439(2) . ?
O21 C20 1.441(2) . ?
O21 C22 1.360(3) . ?
O25 C19 1.191(2) . ?
O18 C13 1.454(2) . ?
O18 C19 1.336(2) . ?
C13 C14 1.518(3) . ?
C13 C12 1.504(3) . ?
C17 C12 1.513(3) . ?
C17 C16 1.512(3) . ?
C19 C20 1.514(3) . ?
C2 C3 1.426(3) . ?
C2 N1 1.362(3) . ?
C2 C7 1.410(3) . ?
C14 C15 1.517(3) . ?
C26 C20 1.502(3) . ?
C26 C27 1.383(3) . ?
C26 C31 1.374(3) . ?
C3 C4 1.378(3) . ?
C4 C5 1.401(3) . ?
N1 C10 1.311(3) . ?
C27 C28 1.363(3) . ?
C7 C6 1.414(3) . ?
C7 C8 1.408(3) . ?
C16 C15 1.516(3) . ?
C22 O23 1.184(3) . ?
C22 C24 1.491(3) . ?
C31 C30 1.390(3) . ?
C10 C9 1.398(4) . ?
C6 C5 1.351(3) . ?
C28 C29 1.359(4) . ?
C8 C9 1.346(4) . ?
C29 C30 1.393(4) . ?

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 O11 C3 118.62(15) . . ?
C22 O21 C20 115.99(18) . . ?
C19 O18 C13 118.29(15) . . ?
C14 C13 O18 108.03(15) . . ?
C12 C13 O18 110.00(14) . . ?
C12 C13 C14 109.71(16) . . ?
C16 C17 C12 111.20(18) . . ?
O18 C19 O25 125.93(18) . . ?
C20 C19 O25 125.60(18) . . ?
C20 C19 O18 108.45(17) . . ?
N1 C2 C3 118.42(19) . . ?
C7 C2 C3 118.8(2) . . ?
C7 C2 N1 122.8(2) . . ?
C15 C14 C13 110.34(17) . . ?
C27 C26 C20 119.1(2) . . ?
C31 C26 C20 121.0(2) . . ?
C31 C26 C27 119.9(2) . . ?
C2 C3 O11 115.36(17) . . ?
C4 C3 O11 124.97(19) . . ?
C4 C3 C2 119.7(2) . . ?
C19 C20 O21 110.22(17) . . ?
C26 C20 O21 106.66(15) . . ?
C26 C20 C19 113.73(17) . . ?
C13 C12 O11 108.25(15) . . ?
C17 C12 O11 112.18(16) . . ?
C17 C12 C13 109.27(15) . . ?
C5 C4 C3 120.5(2) . . ?
C10 N1 C2 116.3(2) . . ?
C28 C27 C26 120.1(3) . . ?
C6 C7 C2 119.7(2) . . ?
C8 C7 C2 117.1(2) . . ?
C8 C7 C6 123.1(2) . . ?
C15 C16 C17 110.79(18) . . ?
O23 C22 O21 122.5(2) . . ?
C24 C22 O21 110.3(2) . . ?
C24 C22 O23 127.2(3) . . ?
C16 C15 C14 111.25(17) . . ?
C30 C31 C26 119.9(3) . . ?
C9 C10 N1 125.7(3) . . ?
C5 C6 C7 120.3(2) . . ?
C29 C28 C27 120.9(3) . . ?
C6 C5 C4 121.1(2) . . ?
C9 C8 C7 120.3(3) . . ?
C8 C9 C10 117.7(3) . . ?
C30 C29 C28 120.0(3) . . ?
C29 C30 C31 119.2(3) . . ?

_olex2_date_sample_data_collection 2017-10-14
_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 1.096
_oxdiff_exptl_absorpt_empirical_full_min 0.942
####################################################################### 
# 
# 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_1311
_database_code_depnum_ccdc_archive 'CCDC 1853113'
_audit_update_record             
;
2018-07-03 deposited with the CCDC.
2018-09-07 downloaded from the CCDC.
;
_audit_creation_date             2018-06-30
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H18 N O2, C8 H7 O3'
_chemical_formula_sum            'C23 H25 N O5'
_chemical_formula_weight         395.44
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'I 2'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z'
3 'x+1/2, y+1/2, z+1/2'
4 '-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   10.7133(9)
_cell_length_b                   12.3487(8)
_cell_length_c                   15.4466(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.908(9)
_cell_angle_gamma                90.00
_cell_volume                     2018.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    949
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.5470
_cell_measurement_theta_min      3.8720
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             804
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4426
_diffrn_reflns_theta_full        29.04
_diffrn_reflns_theta_max         29.04
_diffrn_reflns_theta_min         3.46
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1702
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9972
_diffrn_measured_fraction_theta_max 0.8587
_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  81.00   1.00   36.34    --   19.29  57.00-150.00   82
  2  ω      4.00  83.00   1.00   36.34    --   19.29  57.00 120.00   79
  3  ω     -4.00  43.00   1.00   36.34    --  -20.07  57.00-120.00   47
  4  ω    -21.00  18.00   1.00   36.34    --  -20.07 -99.00  30.00   39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0207136000
_diffrn_orient_matrix_UB_12      0.0035310000
_diffrn_orient_matrix_UB_13      -0.0458174000
_diffrn_orient_matrix_UB_21      -0.0631641000
_diffrn_orient_matrix_UB_22      -0.0088377000
_diffrn_orient_matrix_UB_23      0.0068827000
_diffrn_orient_matrix_UB_31      -0.0084596000
_diffrn_orient_matrix_UB_32      0.0566296000
_diffrn_orient_matrix_UB_33      0.0039232000
_diffrn_oxdiff_ac3_digest_frames 
;
017e049784feef187a8aa5afeffa57bb2a000270204
;
_diffrn_oxdiff_ac3_digest_hkl    
;
010b55cbabdc8f9974a95033bcde47d97e26a6
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2199
_reflns_number_total             3392
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(17)
_refine_ls_extinction_coef       0.0022(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3392
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0569
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0653P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1495
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O -0.3143(2) -0.24318(18) -0.42742(17) 0.0605(7) Uani 1 1 d . . .
O4 O -0.3276(3) -0.7100(2) -0.93026(18) 0.0693(8) Uani 1 1 d . . .
N6 N -0.2409(3) -0.0519(3) -0.4762(2) 0.0527(7) Uani 1 1 d D . .
O8 O -0.3009(3) -0.4083(2) -0.54695(17) 0.0782(9) Uani 1 1 d . . .
H8 H -0.2710 -0.3505 -0.5599 0.117 Uiso 1 1 calc R . .
O10 O -0.4639(3) -0.5964(2) -0.8813(2) 0.0768(9) Uani 1 1 d . . .
O12 O -0.5154(3) -0.7284(3) -0.7600(2) 0.0842(9) Uani 1 1 d . . .
H12 H -0.5511 -0.6758 -0.7850 0.126 Uiso 1 1 calc R . .
C1 C -0.3973(4) 0.0397(3) -0.4064(2) 0.0515(9) Uani 1 1 d . . .
C5 C -0.3476(3) -0.3521(2) -0.4048(2) 0.0518(9) Uani 1 1 d . . .
H5 H -0.4381 -0.3648 -0.4237 0.062 Uiso 1 1 calc R . .
C7 C -0.3851(3) -0.1581(3) -0.4059(2) 0.0478(8) Uani 1 1 d . . .
C8 C -0.1960(4) 0.0421(3) -0.4991(3) 0.0603(10) Uani 1 1 d . . .
H8A H -0.1289 0.0428 -0.5308 0.072 Uiso 1 1 calc R . .
C10 C -0.3388(3) -0.0567(3) -0.4291(2) 0.0479(8) Uani 1 1 d . . .
C11 C -0.2885(4) -0.7494(3) -0.7367(3) 0.0592(10) Uani 1 1 d . . .
C17 C -0.4892(4) -0.1617(3) -0.3661(2) 0.0584(10) Uani 1 1 d . . .
H17 H -0.5227 -0.2283 -0.3535 0.070 Uiso 1 1 calc R . .
C18 C -0.4030(4) -0.6807(3) -0.8779(3) 0.0622(10) Uani 1 1 d . . .
C19 C -0.4102(4) -0.7571(3) -0.8006(3) 0.0657(11) Uani 1 1 d . . .
H19 H -0.4210 -0.8316 -0.8224 0.079 Uiso 1 1 calc R . .
C20 C -0.2700(4) -0.4255(3) -0.4554(2) 0.0608(10) Uani 1 1 d . . .
H20 H -0.1800 -0.4107 -0.4369 0.073 Uiso 1 1 calc R . .
C25 C -0.3129(4) -0.3726(3) -0.3062(3) 0.0588(10) Uani 1 1 d . . .
H25A H -0.2235 -0.3597 -0.2878 0.071 Uiso 1 1 calc R . .
H25B H -0.3600 -0.3239 -0.2740 0.071 Uiso 1 1 calc R . .
C26 C -0.5014(4) 0.0324(3) -0.3613(2) 0.0623(10) Uani 1 1 d . . .
H26 H -0.5388 0.0949 -0.3437 0.075 Uiso 1 1 calc R . .
C27 C -0.3456(4) 0.1384(3) -0.4305(3) 0.0656(12) Uani 1 1 d . . .
H27 H -0.3792 0.2035 -0.4144 0.079 Uiso 1 1 calc R . .
C28 C -0.5467(4) -0.0661(3) -0.3438(2) 0.0623(10) Uani 1 1 d . . .
H28 H -0.6179 -0.0703 -0.3163 0.075 Uiso 1 1 calc R . .
C0AA C -0.3450(4) -0.4903(3) -0.2876(3) 0.0654(11) Uani 1 1 d . . .
H0AA H -0.3255 -0.5044 -0.2251 0.078 Uiso 1 1 calc R . .
H0AB H -0.4347 -0.5028 -0.3058 0.078 Uiso 1 1 calc R . .
C2 C -0.2474(4) 0.1396(3) -0.4768(3) 0.0705(12) Uani 1 1 d . . .
H2 H -0.2151 0.2050 -0.4933 0.085 Uiso 1 1 calc R . .
C4 C -0.1976(5) -0.8294(3) -0.7308(3) 0.0739(13) Uani 1 1 d . . .
H4 H -0.2128 -0.8921 -0.7641 0.089 Uiso 1 1 calc R . .
C6 C -0.2633(4) -0.6570(3) -0.6865(3) 0.0676(11) Uani 1 1 d . . .
H6A H -0.3240 -0.6028 -0.6891 0.081 Uiso 1 1 calc R . .
C3AA C -0.2974(5) -0.5431(3) -0.4352(3) 0.0776(12) Uani 1 1 d . . .
H3AA H -0.2460 -0.5902 -0.4656 0.093 Uiso 1 1 calc R . .
H3AB H -0.3854 -0.5590 -0.4566 0.093 Uiso 1 1 calc R . .
C1AA C -0.2695(5) -0.5663(3) -0.3367(3) 0.0797(13) Uani 1 1 d . . .
H1AA H -0.2914 -0.6408 -0.3257 0.096 Uiso 1 1 calc R . .
H1AB H -0.1800 -0.5568 -0.3160 0.096 Uiso 1 1 calc R . .
C2AA C -0.0837(5) -0.8167(5) -0.6752(4) 0.0884(16) Uani 1 1 d . . .
H2A H -0.0237 -0.8717 -0.6703 0.106 Uiso 1 1 calc R . .
C14 C -0.1481(5) -0.6444(4) -0.6321(3) 0.0839(14) Uani 1 1 d . . .
H14 H -0.1321 -0.5817 -0.5989 0.101 Uiso 1 1 calc R . .
C15 C -0.0590(5) -0.7228(6) -0.6272(4) 0.0959(16) Uani 1 1 d . . .
H15 H 0.0186 -0.7134 -0.5916 0.115 Uiso 1 1 calc R . .
H6 H -0.204(5) -0.109(3) -0.493(4) 0.13(2) Uiso 1 1 d D . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C5 1.449(4) . ?
O3 C7 1.367(4) . ?
O4 C18 1.280(5) . ?
N6 C8 1.325(5) . ?
N6 C10 1.368(4) . ?
O8 C20 1.418(5) . ?
O10 C18 1.226(5) . ?
O12 C19 1.418(5) . ?
C1 C10 1.414(5) . ?
C1 C26 1.406(5) . ?
C1 C27 1.412(5) . ?
C5 C20 1.524(5) . ?
C5 C25 1.532(5) . ?
C7 C10 1.414(5) . ?
C7 C17 1.355(5) . ?
C8 C2 1.390(6) . ?
C11 C19 1.512(5) . ?
C11 C4 1.380(5) . ?
C11 C6 1.382(5) . ?
C17 C28 1.400(5) . ?
C18 C19 1.533(6) . ?
C20 C3AA 1.523(5) . ?
C25 C0AA 1.531(5) . ?
C26 C28 1.352(6) . ?
C27 C2 1.361(6) . ?
C0AA C1AA 1.518(6) . ?
C4 C2AA 1.388(7) . ?
C6 C14 1.390(6) . ?
C3AA C1AA 1.532(6) . ?
C2AA C15 1.379(8) . ?
C14 C15 1.353(7) . ?

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
C7 O3 C5 119.2(3) . . ?
C8 N6 C10 121.3(3) . . ?
C26 C1 C10 119.0(3) . . ?
C26 C1 C27 124.0(4) . . ?
C27 C1 C10 117.0(3) . . ?
O3 C5 C20 104.7(3) . . ?
O3 C5 C25 111.2(3) . . ?
C20 C5 C25 110.1(3) . . ?
O3 C7 C10 112.9(3) . . ?
C17 C7 O3 127.7(3) . . ?
C17 C7 C10 119.4(3) . . ?
N6 C8 C2 121.2(4) . . ?
N6 C10 C1 120.1(3) . . ?
N6 C10 C7 120.1(3) . . ?
C7 C10 C1 119.7(3) . . ?
C4 C11 C19 121.8(4) . . ?
C4 C11 C6 118.6(4) . . ?
C6 C11 C19 119.5(3) . . ?
C7 C17 C28 120.6(4) . . ?
O4 C18 C19 115.5(3) . . ?
O10 C18 O4 126.6(4) . . ?
O10 C18 C19 117.7(4) . . ?
O12 C19 C11 111.1(3) . . ?
O12 C19 C18 109.3(3) . . ?
C11 C19 C18 109.1(3) . . ?
O8 C20 C5 111.1(3) . . ?
O8 C20 C3AA 108.9(3) . . ?
C3AA C20 C5 108.9(3) . . ?
C0AA C25 C5 108.5(3) . . ?
C28 C26 C1 119.6(4) . . ?
C2 C27 C1 121.0(4) . . ?
C26 C28 C17 121.6(4) . . ?
C1AA C0AA C25 109.9(4) . . ?
C27 C2 C8 119.3(4) . . ?
C11 C4 C2AA 120.2(4) . . ?
C11 C6 C14 120.6(4) . . ?
C20 C3AA C1AA 111.5(3) . . ?
C0AA C1AA C3AA 110.1(3) . . ?
C15 C2AA C4 120.3(5) . . ?
C15 C14 C6 120.4(5) . . ?
C14 C15 C2AA 119.7(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 1.758
_oxdiff_exptl_absorpt_empirical_full_min 0.725
####################################################################### 
# 
# 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_1443
_database_code_depnum_ccdc_archive 'CCDC 1853116'
_audit_update_record             
;
2018-07-03 deposited with the CCDC.
2018-09-07 downloaded from the CCDC.
;
_audit_creation_date             2018-07-02
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C15 H17 N O2), H2 O'
_chemical_formula_sum            'C30 H36 N2 O5'
_chemical_formula_weight         504.61
_chemical_absolute_configuration rm
_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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, z+1/2'
3 'x, -y, -z'
4 '-x, y, -z+1/2'
5 'x+1/2, y+1/2, z'
6 '-x+1/2, -y+1/2, z+1/2'
7 'x+1/2, -y+1/2, -z'
8 '-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   8.3581(6)
_cell_length_b                   22.439(2)
_cell_length_c                   14.0407(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2633.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1097
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7740
_cell_measurement_theta_min      3.8830
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3560
_diffrn_reflns_theta_full        28.74
_diffrn_reflns_theta_max         28.74
_diffrn_reflns_theta_min         3.66
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1702
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max ?
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  92.00   1.00    1.00    --   19.76  19.00 -30.00  117
  2  ω    -25.00   0.00   1.00    1.00    --  -20.54 -99.00   0.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0312501000
_diffrn_orient_matrix_UB_12      0.0160205000
_diffrn_orient_matrix_UB_13      0.0393549000
_diffrn_orient_matrix_UB_21      -0.0267601000
_diffrn_orient_matrix_UB_22      -0.0227513000
_diffrn_orient_matrix_UB_23      0.0312872000
_diffrn_orient_matrix_UB_31      0.0742391000
_diffrn_orient_matrix_UB_32      -0.0149343000
_diffrn_orient_matrix_UB_33      -0.0053184000
_diffrn_oxdiff_ac3_digest_frames 
;
015c35f5b755ffc99341ccf92925ed117800150f47e
;
_diffrn_oxdiff_ac3_digest_hkl    
;
0193efa6ec2b3978d8e9bb88ea5f90d5b23396
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2073
_reflns_number_total             2607
_reflns_odcompleteness_completeness 99.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXH-1997 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(15)
_refine_ls_extinction_coef       0.0120(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2607
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0436P)²+0.3043P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.1011
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16A,H16B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C5(H5), C7(H7), C9(H9), C8(H8)
2.d Idealised tetrahedral OH refined as rotating group:
 O18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
O11 O -0.20738(15) -0.33846(5) -0.86514(11) 0.0488(4) Uani 1 d . . 1 . . .
C1 C -0.1667(2) -0.44141(8) -0.86998(14) 0.0429(4) Uani 1 d . . 1 . . .
N10 N -0.3286(2) -0.44654(7) -0.86137(14) 0.0536(5) Uani 1 d . . 1 . . .
C12 C -0.1525(2) -0.27782(8) -0.86321(15) 0.0407(4) Uani 1 d . . 1 . . .
H12 H -0.0517 -0.2757 -0.8277 0.049 Uiso 1 calc . . 1 R . .
C6 C -0.0650(3) -0.49091(9) -0.87645(14) 0.0486(5) Uani 1 d . . 1 . . .
C2 C -0.0992(2) -0.38329(8) -0.87083(14) 0.0413(4) Uani 1 d . . 1 . . .
C4 C 0.1620(3) -0.42672(10) -0.88113(16) 0.0547(6) Uani 1 d . . 1 . . .
H4 H 0.2723 -0.4214 -0.8837 0.066 Uiso 1 calc . . 1 R . .
C3 C 0.0622(2) -0.37669(9) -0.87628(15) 0.0476(5) Uani 1 d . . 1 . . .
H3 H 0.1067 -0.3387 -0.8768 0.057 Uiso 1 calc . . 1 R . .
O18 O -0.29727(19) -0.26308(7) -0.71561(10) 0.0619(4) Uani 1 d . . 1 . . .
H18 H -0.3485 -0.2942 -0.7154 0.093 Uiso 1 calc . . 1 GR . .
C5 C 0.1017(3) -0.48239(10) -0.88213(16) 0.0563(6) Uani 1 d . . 1 . . .
H5 H 0.1699 -0.5150 -0.8865 0.068 Uiso 1 calc . . 1 R . .
C13 C -0.1263(2) -0.25426(9) -0.96234(15) 0.0504(5) Uani 1 d . . 1 . . .
H13A H -0.2241 -0.2582 -0.9990 0.061 Uiso 1 calc . . 1 R . .
H13B H -0.0436 -0.2774 -0.9937 0.061 Uiso 1 calc . . 1 R . .
C17 C -0.2796(2) -0.24266(9) -0.81066(13) 0.0452(5) Uani 1 d . . 1 . . .
H17 H -0.3819 -0.2470 -0.8441 0.054 Uiso 1 calc . . 1 R . .
C16 C -0.2342(2) -0.17782(9) -0.80820(17) 0.0564(6) Uani 1 d . . 1 . . .
H16A H -0.1399 -0.1730 -0.7687 0.068 Uiso 1 calc . . 1 R . .
H16B H -0.3205 -0.1553 -0.7792 0.068 Uiso 1 calc . . 1 R . .
C7 C -0.1370(3) -0.54718(10) -0.87890(19) 0.0661(7) Uani 1 d . . 1 . . .
H7 H -0.0740 -0.5812 -0.8846 0.079 Uiso 1 calc . . 1 R . .
C9 C -0.3890(3) -0.50071(10) -0.8635(2) 0.0697(7) Uani 1 d . . 1 . . .
H9 H -0.4994 -0.5048 -0.8584 0.084 Uiso 1 calc . . 1 R . .
C14 C -0.0768(3) -0.18925(9) -0.95840(19) 0.0642(6) Uani 1 d . . 1 . . .
H14A H 0.0256 -0.1858 -0.9263 0.077 Uiso 1 calc . . 1 R . .
H14B H -0.0645 -0.1740 -1.0226 0.077 Uiso 1 calc . . 1 R . .
C8 C -0.2975(4) -0.55221(11) -0.8730(2) 0.0768(7) Uani 1 d . . 1 . . .
H8 H -0.3463 -0.5894 -0.8751 0.092 Uiso 1 calc . . 1 R . .
C15 C -0.2003(3) -0.15263(10) -0.90601(18) 0.0649(7) Uani 1 d . . 1 . . .
H15A H -0.2986 -0.1518 -0.9427 0.078 Uiso 1 calc . . 1 R . .
H15B H -0.1621 -0.1120 -0.8997 0.078 Uiso 1 calc . . 1 R . .
O1 O -0.5000 -0.35946(12) -0.7500 0.0752(8) Uani 1 d . . 2 S T P
H1 H -0.440(4) -0.3836(12) -0.790(2) 0.121(12) Uiso 1 d . . 1 . . .


_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
O11 C12 1.436(2) . ?
O11 C2 1.355(2) . ?
C1 N10 1.363(3) . ?
C1 C6 1.402(3) . ?
C1 C2 1.421(3) . ?
N10 C9 1.317(3) . ?
C12 C13 1.505(3) . ?
C12 C17 1.515(3) . ?
C6 C5 1.409(3) . ?
C6 C7 1.399(3) . ?
C2 C3 1.360(3) . ?
C4 C3 1.400(3) . ?
C4 C5 1.347(3) . ?
O18 C17 1.419(2) . ?
C13 C14 1.517(3) . ?
C17 C16 1.504(3) . ?
C16 C15 1.512(3) . ?
C7 C8 1.350(4) . ?
C9 C8 1.392(4) . ?
C14 C15 1.510(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O11 C12 119.43(14) . . ?
N10 C1 C6 122.74(18) . . ?
N10 C1 C2 118.18(17) . . ?
C6 C1 C2 119.07(18) . . ?
C9 N10 C1 117.16(19) . . ?
O11 C12 C13 111.20(16) . . ?
O11 C12 C17 106.18(14) . . ?
C13 C12 C17 111.69(16) . . ?
C1 C6 C5 119.7(2) . . ?
C7 C6 C1 117.1(2) . . ?
C7 C6 C5 123.1(2) . . ?
O11 C2 C1 114.58(16) . . ?
O11 C2 C3 125.79(19) . . ?
C3 C2 C1 119.63(19) . . ?
C5 C4 C3 121.4(2) . . ?
C2 C3 C4 120.4(2) . . ?
C4 C5 C6 119.7(2) . . ?
C12 C13 C14 110.09(18) . . ?
O18 C17 C12 111.30(16) . . ?
O18 C17 C16 108.48(16) . . ?
C16 C17 C12 109.77(16) . . ?
C17 C16 C15 112.84(18) . . ?
C8 C7 C6 120.1(2) . . ?
N10 C9 C8 123.9(2) . . ?
C15 C14 C13 110.78(19) . . ?
C7 C8 C9 118.9(2) . . ?
C14 C15 C16 111.53(18) . . ?

_olex2_date_sample_data_collection 2018-03-25
_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 1.115
_oxdiff_exptl_absorpt_empirical_full_min 0.840
####################################################################### 
# 
# 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_965
_database_code_depnum_ccdc_archive 'CCDC 1853115'
_audit_update_record             
;
2018-07-03 deposited with the CCDC.
2018-09-07 downloaded from the CCDC.
;
_audit_creation_date             2018-07-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_formula_moiety         '2(C15 H17 N O2), H2 O'
_chemical_formula_sum            'C30 H36 N2 O5'
_chemical_formula_weight         504.61
_chemical_absolute_configuration rm
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 0.00347 0.00161 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 0.01158 0.00611 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'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'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           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           ' C 2c 2'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x,-y,-z
3 -x,y,-z+1/2
4 -x,-y,z+1/2
5 x+1/2,y+1/2,z
6 x+1/2,-y+1/2,-z
7 -x+1/2,y+1/2,-z+1/2
8 -x+1/2,-y+1/2,z+1/2

_symmetry_Int_Tables_number      20
_cell_length_a                   8.4035(9)
_cell_length_b                   22.609(2)
_cell_length_c                   14.0695(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2673.1(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2691
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7530
_cell_measurement_theta_min      4.6010
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.2538
_exptl_crystal_F_000             1080.5420
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8210
_diffrn_ambient_temperature      293(2)
_diffrn_reflns_theta_full        28.6677
_diffrn_reflns_theta_max         28.67
_diffrn_reflns_theta_min         3.41
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0851
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 0.8607
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  63.00   1.00    2.23    --   19.44 -99.00   0.00   88
  2  ω    -54.00  93.00   1.00    2.23    --   19.44   0.00-150.00  147
  3  ω    -30.00  59.00   1.00    2.23    --   19.44  19.00  30.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0004210000
_diffrn_orient_matrix_UB_12      -0.0267878000
_diffrn_orient_matrix_UB_13      -0.0262022000
_diffrn_orient_matrix_UB_21      -0.0196824000
_diffrn_orient_matrix_UB_22      0.0158625000
_diffrn_orient_matrix_UB_23      -0.0418617000
_diffrn_orient_matrix_UB_31      0.0821342000
_diffrn_orient_matrix_UB_32      0.0039425000
_diffrn_orient_matrix_UB_33      -0.0098888000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.792
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              30
_reflns_limit_k_min              -29
_reflns_limit_l_max              18
_reflns_limit_l_min              -18
_reflns_number_gt                2425
_reflns_number_total             2971
_reflns_odcompleteness_completeness 99.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.1517
_refine_diff_density_min         -0.1477
_refine_diff_density_rms         0.0321
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -1.5(5)
_refine_ls_d_res_high            0.7408
_refine_ls_d_res_low             5.9727
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0419
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2971
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.0419
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0399P)²+0.3874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0902
_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 O(H) groups
2. Others
 Fixed Sof: H1a(0.5) H1b(0.5)
3.a Ternary CH refined with riding coordinates:
 C12(H12), C17(H17)
3.b Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b), C16(H16a,H16b), C15(H15a,H15b), C14(H14a,H14b)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C5(H5), C9(H9), C10(H10), C8(H8)
3.d Idealised tetrahedral OH refined as rotating group:
 O18(H18)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
O11 O 0.79236(12) 0.33852(4) 0.63477(8) 0.0473(3) Uani 1.000000 1 . . .
O18 O 0.70271(16) 0.26305(6) 0.78445(8) 0.0611(4) Uani 1.000000 1 . . .
H18 H 0.657(3) 0.2950(5) 0.78441(14) 0.0917(5) Uiso 1.000000 1 GR . .
C12 C 0.84791(16) 0.27787(6) 0.63695(11) 0.0398(3) Uani 1.000000 1 . . .
H12 H 0.94809(16) 0.27580(6) 0.67246(11) 0.0478(4) Uiso 1.000000 1 R . .
C3 C 0.90053(17) 0.38320(6) 0.62915(11) 0.0400(3) Uani 1.000000 1 . . .
C17 C 0.72000(18) 0.24269(7) 0.68949(11) 0.0440(4) Uani 1.000000 1 . . .
H17 H 0.61832(18) 0.24700(7) 0.65609(11) 0.0528(4) Uiso 1.000000 1 R . .
N1 N 0.67130(17) 0.44669(6) 0.63825(11) 0.0540(4) Uani 1.000000 1 . . .
C13 C 0.8734(2) 0.25431(7) 0.53762(12) 0.0486(4) Uani 1.000000 1 . . .
H13a H 0.7758(2) 0.25805(7) 0.50135(12) 0.0583(5) Uiso 1.000000 1 R . .
H13b H 0.9552(2) 0.27729(7) 0.50598(12) 0.0583(5) Uiso 1.000000 1 R . .
C16 C 0.7662(2) 0.17770(7) 0.69188(13) 0.0558(4) Uani 1.000000 1 . . .
H16a H 0.8603(2) 0.17302(7) 0.73113(13) 0.0670(5) Uiso 1.000000 1 R . .
H16b H 0.6808(2) 0.15525(7) 0.72099(13) 0.0670(5) Uiso 1.000000 1 R . .
C2 C 0.83193(19) 0.44136(6) 0.63014(11) 0.0422(3) Uani 1.000000 1 . . .
C4 C 1.06218(19) 0.37663(7) 0.62382(12) 0.0463(4) Uani 1.000000 1 . . .
H4 H 1.10626(19) 0.33890(7) 0.62345(12) 0.0556(4) Uiso 1.000000 1 R . .
C15 C 0.7995(2) 0.15280(7) 0.59418(14) 0.0637(5) Uani 1.000000 1 . . .
H15a H 0.8373(2) 0.11243(7) 0.60025(14) 0.0764(6) Uiso 1.000000 1 R . .
H15b H 0.7017(2) 0.15209(7) 0.55765(14) 0.0764(6) Uiso 1.000000 1 R . .
C14 C 0.9234(2) 0.18946(7) 0.54156(15) 0.0629(5) Uani 1.000000 1 . . .
H14a H 0.9359(2) 0.17436(7) 0.47746(15) 0.0754(6) Uiso 1.000000 1 R . .
H14b H 1.0252(2) 0.18614(7) 0.57366(15) 0.0754(6) Uiso 1.000000 1 R . .
C6 C 1.1017(2) 0.48237(8) 0.61794(12) 0.0559(4) Uani 1.000000 1 . . .
H6 H 1.1694(2) 0.51481(8) 0.61367(12) 0.0671(5) Uiso 1.000000 1 R . .
C5 C 1.1630(2) 0.42675(7) 0.61885(12) 0.0529(4) Uani 1.000000 1 . . .
H5 H 1.2727(2) 0.42152(7) 0.61618(12) 0.0635(5) Uiso 1.000000 1 R . .
C7 C 0.9354(2) 0.49106(7) 0.62346(12) 0.0484(4) Uani 1.000000 1 . . .
C9 C 0.7031(3) 0.55239(8) 0.62726(17) 0.0753(6) Uani 1.000000 1 . . .
H9 H 0.6546(3) 0.58934(8) 0.62540(17) 0.0903(7) Uiso 1.000000 1 R . .
C10 C 0.6112(2) 0.50068(8) 0.63657(17) 0.0683(5) Uani 1.000000 1 . . .
H10 H 0.5014(2) 0.50476(8) 0.64185(17) 0.0820(6) Uiso 1.000000 1 R . .
C8 C 0.8634(3) 0.54751(7) 0.62105(15) 0.0659(5) Uani 1.000000 1 . . .
H8 H 0.9260(3) 0.58124(7) 0.61521(15) 0.0790(6) Uiso 1.000000 1 R . .
O1 O 0.5 0.64066(9) 0.25 0.0738(6) Uani 1.000000 2 S T P
H1 H 0.547(3) 0.6175(9) 0.2886(18) 0.097(8) Uiso 1.000000 1 . . .


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
O11 C12 1.4488(16) . ?
O11 C3 1.3614(17) . ?
O18 C17 1.4206(19) . ?
C12 C17 1.528(2) . ?
C12 C13 1.511(2) . ?
C3 C2 1.4358(19) . ?
C3 C4 1.369(2) . ?
C17 C16 1.520(2) . ?
N1 C2 1.360(2) . ?
N1 C10 1.321(2) . ?
C13 C14 1.526(2) . ?
C16 C15 1.512(3) . ?
C2 C7 1.424(2) . ?
C4 C5 1.416(2) . ?
C15 C14 1.523(3) . ?
C6 C5 1.359(2) . ?
C6 C7 1.414(3) . ?
C7 C8 1.413(2) . ?
C9 C10 1.408(3) . ?
C9 C8 1.354(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O11 C12 119.24(11) . . ?
C17 C12 O11 106.04(11) . . ?
C13 C12 O11 111.08(12) . . ?
C13 C12 C17 111.33(12) . . ?
C2 C3 O11 114.27(12) . . ?
C4 C3 O11 125.83(13) . . ?
C4 C3 C2 119.90(13) . . ?
C12 C17 O18 111.00(12) . . ?
C16 C17 O18 108.57(13) . . ?
C16 C17 C12 109.52(13) . . ?
C10 N1 C2 117.38(15) . . ?
C14 C13 C12 110.13(14) . . ?
C15 C16 C17 112.78(14) . . ?
N1 C2 C3 118.71(13) . . ?
C7 C2 C3 118.49(14) . . ?
C7 C2 N1 122.79(13) . . ?
C5 C4 C3 120.63(15) . . ?
C14 C15 C16 111.47(14) . . ?
C15 C14 C13 110.61(15) . . ?
C7 C6 C5 120.19(15) . . ?
C6 C5 C4 120.93(16) . . ?
C6 C7 C2 119.84(15) . . ?
C8 C7 C2 116.95(16) . . ?
C8 C7 C6 123.20(16) . . ?
C8 C9 C10 118.97(17) . . ?
C9 C10 N1 123.98(19) . . ?
C9 C8 C7 119.87(17) . . ?

_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 1.138
_oxdiff_exptl_absorpt_empirical_full_min 0.799
