# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_8633
_database_code_depnum_ccdc_archive 'CCDC 1570751'
_audit_update_record             
;
2017-08-24 deposited with the CCDC.
2017-10-27 downloaded from the CCDC.
;
_audit_creation_date             2017-08-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '1.33(C19 H19 N O)'
_chemical_formula_sum            'C25.333 H25.333 N1.333 O1.333'
_chemical_formula_weight         369.82
_chemical_oxdiff_formula         'C23 N2 H14 O2'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 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      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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   14.0947(4)
_cell_length_b                   5.86763(14)
_cell_length_c                   18.4634(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.511(3)
_cell_angle_gamma                90
_cell_volume                     1513.87(7)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    2441
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.3110
_cell_measurement_theta_min      4.8240
_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2169
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             593.7117
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4979
_diffrn_reflns_theta_full        69.8959
_diffrn_reflns_theta_max         69.90
_diffrn_reflns_theta_min         4.83
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9776
_diffrn_measured_fraction_theta_max 0.9776
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     20.00  69.00   1.00    1.90    --    0.00  57.00  30.00   49
  2  ω     82.00 123.00   1.00    7.61    --   54.00  57.00 -90.00   41
  3  ω    130.00 175.00   1.00    7.61    --  108.00 111.00-180.00   45
  4  ω    122.00 176.00   1.00    7.61    --  108.00  38.00-150.00   54
  5  ω     83.00 176.00   1.00    7.61    --  108.00  64.00 -90.00   93
  6  ω     77.00 149.00   1.00    7.61    --  108.00 178.00-150.00   72
  7  ω    -15.00  68.00   1.00    7.61    --   54.00 -57.00 120.00   83
  8  ω     29.00 110.00   1.00    7.61    --   54.00-125.00 120.00   81
  9  ω     68.00  93.00   1.00    7.61    --  108.00-111.00  30.00   25
 10  ω     40.00  91.00   1.00    7.61    --  108.00-111.00 -30.00   51
 11  ω     38.00 131.00   1.00    7.61    --  108.00 -50.00 120.00   93
 12  ω    -11.00  75.00   1.00    7.61    --   54.00 -57.00-150.00   86
 13  ω     63.00 115.00   1.00    7.61    --  108.00-111.00-180.00   52
 14  ω    -66.00 -16.00   1.00    1.90    --    0.00 -57.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0937714000
_diffrn_orient_matrix_UB_12      0.1050760000
_diffrn_orient_matrix_UB_13      -0.0378569000
_diffrn_orient_matrix_UB_21      -0.0301458000
_diffrn_orient_matrix_UB_22      0.0573529000
_diffrn_orient_matrix_UB_23      0.0751661000
_diffrn_orient_matrix_UB_31      0.0495646000
_diffrn_orient_matrix_UB_32      0.2335847000
_diffrn_orient_matrix_UB_33      -0.0014117000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -17
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                2065
_reflns_number_total             2797
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.3144
_refine_diff_density_min         -0.3126
_refine_diff_density_rms         0.0874
_refine_ls_d_res_high            0.8209
_refine_ls_d_res_low             9.1525
_refine_ls_goodness_of_fit_ref   1.2425
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    31
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2797
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0581
_refine_ls_restrained_S_all      1.2425
_refine_ls_shift/su_max          0.08
_refine_ls_shift/su_mean         0.0052
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1844
_refine_ls_wR_factor_ref         0.2002
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N1(H1a,H1b)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C11(H11a,H11b)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C17(H17), C19(H19), C2(H2), C16(H16), C3(H3), C15(H15)
2.d Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C7(H7a,H7b,H7c)
;
_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
O1 O 0.76646(12) 0.1264(3) 0.30727(9) 0.0553(5) Uani 1.000000 .
C5 C 0.73565(16) 0.6044(4) 0.42266(12) 0.0462(6) Uani 1.000000 .
H5 H 0.77452(16) 0.7154(4) 0.44721(12) 0.0554(7) Uiso 1.000000 R
C6 C 0.77479(15) 0.4431(4) 0.38141(11) 0.0411(5) Uani 1.000000 .
C17 C 1.35846(17) -0.0946(4) 0.34030(13) 0.0507(6) Uani 1.000000 .
H17 H 1.41503(17) -0.1455(4) 0.32493(13) 0.0608(7) Uiso 1.000000 R
C18 C 1.32043(16) 0.1142(4) 0.31618(12) 0.0452(6) Uani 1.000000 .
C19 C 1.23641(15) 0.1871(4) 0.34099(12) 0.0453(6) Uani 1.000000 .
H19 H 1.21070(15) 0.3280(4) 0.32605(12) 0.0544(7) Uiso 1.000000 R
C9 C 0.85797(16) 0.2347(4) 0.30237(13) 0.0482(6) Uani 1.000000 .
H9a H 0.90829(16) 0.1213(4) 0.30433(13) 0.0579(7) Uiso 1.000000 R
H9b H 0.85584(16) 0.3183(4) 0.25686(13) 0.0579(7) Uiso 1.000000 R
C12 C 1.02559(16) 0.1961(4) 0.42397(13) 0.0485(6) Uani 1.000000 .
C14 C 1.19013(15) 0.0528(4) 0.38779(12) 0.0453(6) Uani 1.000000 .
C1 C 0.71698(16) 0.2769(4) 0.34565(12) 0.0458(6) Uani 1.000000 .
C4 C 0.63729(17) 0.6021(4) 0.42783(12) 0.0489(6) Uani 1.000000 .
C8 C 0.87672(15) 0.3977(4) 0.36772(12) 0.0413(5) Uani 1.000000 .
C13 C 1.10027(16) 0.1299(4) 0.40929(13) 0.0490(6) Uani 1.000000 .
C11 C 0.92945(16) 0.2724(4) 0.43507(12) 0.0466(6) Uani 1.000000 .
H11a H 0.89191(16) 0.1412(4) 0.44598(12) 0.0559(7) Uiso 1.000000 R
H11b H 0.93446(16) 0.3737(4) 0.47691(12) 0.0559(7) Uiso 1.000000 R
C2 C 0.61978(17) 0.2690(5) 0.34889(15) 0.0560(7) Uani 1.000000 .
H2 H 0.58142(17) 0.1572(5) 0.32427(15) 0.0672(8) Uiso 1.000000 R
C16 C 1.31296(18) -0.2270(4) 0.38685(14) 0.0551(6) Uani 1.000000 .
H16 H 1.33956(18) -0.3663(4) 0.40260(14) 0.0661(8) Uiso 1.000000 R
N1 N 1.36677(15) 0.2523(4) 0.27056(12) 0.0602(6) Uani 1.000000 .
H1a H 1.3945(13) 0.1678(4) 0.2416(8) 0.0722(7) Uiso 1.000000 GR
H1b H 1.3248(3) 0.337(3) 0.2454(9) 0.0722(7) Uiso 1.000000 GR
C3 C 0.58168(17) 0.4338(5) 0.39023(13) 0.0562(7) Uani 1.000000 .
H3 H 0.51626(17) 0.4319(5) 0.39294(13) 0.0674(8) Uiso 1.000000 R
C10 C 0.93139(18) 0.6103(4) 0.35013(16) 0.0591(7) Uani 1.000000 .
H10a H 0.8959(7) 0.6892(18) 0.3098(7) 0.0886(10) Uiso 1.000000 GR
H10b H 0.9399(12) 0.7086(16) 0.3920(4) 0.0886(10) Uiso 1.000000 GR
H10c H 0.9928(6) 0.5671(5) 0.3375(10) 0.0886(10) Uiso 1.000000 GR
C15 C 1.22871(18) -0.1573(4) 0.41062(14) 0.0533(6) Uani 1.000000 .
H15 H 1.19823(18) -0.2495(4) 0.44144(14) 0.0640(8) Uiso 1.000000 R
C7 C 0.5932(2) 0.7771(5) 0.47294(14) 0.0652(8) Uani 1.000000 .
H7a H 0.6146(12) 0.751(2) 0.52379(16) 0.0978(12) Uiso 1.000000 GR
H7b H 0.6121(12) 0.9269(6) 0.4596(8) 0.0978(12) Uiso 1.000000 GR
H7c H 0.5247(2) 0.765(2) 0.4642(9) 0.0978(12) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.451(3) . ?
O1 C1 1.378(3) . ?
C5 C6 1.375(3) . ?
C5 C4 1.402(3) . ?
C6 C1 1.382(3) . ?
C6 C8 1.515(3) . ?
C17 C18 1.387(3) . ?
C17 C16 1.378(3) . ?
C18 C19 1.392(3) . ?
C18 N1 1.392(3) . ?
C19 C14 1.393(3) . ?
C9 C8 1.535(3) . ?
C12 C13 1.186(3) . ?
C12 C11 1.467(3) . ?
C14 C13 1.448(3) . ?
C14 C15 1.390(3) . ?
C1 C2 1.380(3) . ?
C4 C3 1.389(3) . ?
C4 C7 1.507(3) . ?
C8 C11 1.548(3) . ?
C8 C10 1.523(3) . ?
C2 C3 1.383(4) . ?
C16 C15 1.381(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
C1 O1 C9 105.36(17) . . ?
C4 C5 C6 120.2(2) . . ?
C1 C6 C5 119.7(2) . . ?
C8 C6 C5 132.2(2) . . ?
C8 C6 C1 108.02(19) . . ?
C16 C17 C18 120.4(2) . . ?
C19 C18 C17 118.4(2) . . ?
N1 C18 C17 121.1(2) . . ?
N1 C18 C19 120.5(2) . . ?
C14 C19 C18 121.2(2) . . ?
C8 C9 O1 106.68(17) . . ?
C11 C12 C13 174.6(2) . . ?
C13 C14 C19 119.4(2) . . ?
C15 C14 C19 119.6(2) . . ?
C15 C14 C13 121.0(2) . . ?
C6 C1 O1 113.06(19) . . ?
C2 C1 O1 124.9(2) . . ?
C2 C1 C6 122.0(2) . . ?
C3 C4 C5 118.1(2) . . ?
C7 C4 C5 120.9(2) . . ?
C7 C4 C3 120.9(2) . . ?
C9 C8 C6 99.84(17) . . ?
C11 C8 C6 108.40(17) . . ?
C11 C8 C9 110.52(19) . . ?
C10 C8 C6 114.15(19) . . ?
C10 C8 C9 112.5(2) . . ?
C10 C8 C11 110.92(19) . . ?
C14 C13 C12 177.2(2) . . ?
C8 C11 C12 112.83(18) . . ?
C3 C2 C1 117.4(2) . . ?
C15 C16 C17 121.4(2) . . ?
C2 C3 C4 122.6(2) . . ?
C16 C15 C14 119.0(2) . . ?

_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 6.569
_oxdiff_exptl_absorpt_empirical_full_min 0.702
