# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_157
_database_code_depnum_ccdc_archive 'CCDC 1922750'
loop_
_audit_author_name
_audit_author_address
Yaofeng
;Guangdong Pharmaceutical University
China
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-07-01 downloaded from the CCDC.
;
_audit_creation_date             2019-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 N O2'
_chemical_formula_sum            'C19 H15 N O2'
_chemical_formula_weight         289.32
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   3.9198(2)
_cell_length_b                   25.3323(11)
_cell_length_c                   7.1542(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.305(5)
_cell_angle_gamma                90
_cell_volume                     704.62(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2410
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.2820
_cell_measurement_theta_min      6.4760
_shelx_estimated_absorpt_T_max   0.926
_shelx_estimated_absorpt_T_min   0.913
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41660
_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            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_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  0.0177
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3274
_diffrn_reflns_point_group_measured_fraction_full 0.820
_diffrn_reflns_point_group_measured_fraction_max 0.790
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.339
_diffrn_reflns_theta_min         6.237
_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 0.996
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     17.00  82.00   1.00    1.00    --   40.73  38.00-120.00   65
  2  ω     95.00 135.00   1.00    1.00    --  106.95 125.00 -30.00   40
  3  ω    135.00 173.00   1.00    1.00    --  106.95  45.00  30.00   38
  4  ω     99.00 160.00   1.00    1.00    --  106.95 125.00-150.00   61
  5  ω     84.00 132.00   1.00    1.00    --  106.95 -30.00-150.00   48
  6  ω     51.00  92.00   1.00    1.00    --  106.95 -95.00 -30.00   41
  7  ω     76.00 112.00   1.00    1.00    --  106.95 -45.00  30.00   36
  8  ω     43.00 115.00   1.00    1.00    --  106.95 -30.00 -60.00   72
  9  ω     36.00  82.00   1.00    1.00    --  106.95 -30.00-150.00   46
 10  ω      4.00  36.00   1.00    1.00    --   40.73 -99.00 -30.00   32
 11  ω    -65.00 -13.00   1.00    1.00    --  -40.73 -57.00  90.00   52
 12  ω   -110.00 -70.00   1.00    1.00    --  -40.73 -57.00  90.00   40
 13  ω    -82.00  29.00   1.00    1.00    --  -41.23  19.00-180.00  111
 14  ω     76.00 104.00   1.00    1.00    --   41.23  38.00 150.00   28
 15  ω     33.00  59.00   1.00    1.00    --   41.23  38.00 150.00   26
 16  ω     21.00  47.00   1.00    1.00    --   41.23 -99.00-120.00   26
 17  ω     74.00 133.00   1.00    1.00    --  106.95  77.00  90.00   59
 18  ω     81.00 108.00   1.00    1.00    --  106.95  77.00  60.00   27
;
_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      0.2770233000
_diffrn_orient_matrix_UB_12      0.0040857000
_diffrn_orient_matrix_UB_13      0.1725799000
_diffrn_orient_matrix_UB_21      0.2115052000
_diffrn_orient_matrix_UB_22      0.0372737000
_diffrn_orient_matrix_UB_23      -0.1106706000
_diffrn_orient_matrix_UB_31      -0.1884228000
_diffrn_orient_matrix_UB_32      0.0478868000
_diffrn_orient_matrix_UB_33      0.0713890000
_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         0.583
_reflns_Friedel_fraction_full    0.636
_reflns_Friedel_fraction_max     0.596
_reflns_number_gt                2173
_reflns_number_total             2230
_reflns_odcompleteness_completeness 99.55
_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         0.195
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 
;
 Flack x determined using 767 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2230
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.067
_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)+(0.0543P)²+0.2345P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.0966
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C2(H2), C16(H16), C9(H9), C6(H6), C5(H5), C7(H7), C15(H15)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), 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
O2 O 0.8384(5) 0.34175(8) 0.3539(3) 0.0287(5) Uani 1 1 d . . . . .
O1 O 0.6946(6) 0.30367(8) 0.6179(3) 0.0335(5) Uani 1 1 d . . . . .
N1 N 0.4518(6) 0.46127(9) 0.7413(3) 0.0210(5) Uani 1 1 d . . . . .
C11 C 0.5603(7) 0.58356(10) 0.4851(4) 0.0221(6) Uani 1 1 d . . . . .
C12 C 0.6949(8) 0.57280(11) 0.3182(4) 0.0250(6) Uani 1 1 d . . . . .
H12 H 0.744423 0.538075 0.289136 0.030 Uiso 1 1 calc R . . . .
C1 C 0.5548(7) 0.48536(10) 0.5871(4) 0.0211(6) Uani 1 1 d . . . . .
C18 C 0.7226(7) 0.34318(11) 0.5242(4) 0.0239(6) Uani 1 1 d . . . . .
C13 C 0.7566(8) 0.61275(12) 0.1945(4) 0.0274(6) Uani 1 1 d . . . . .
H13 H 0.846715 0.604348 0.084099 0.033 Uiso 1 1 calc R . . . .
C3 C 0.6376(7) 0.39613(11) 0.5788(4) 0.0228(6) Uani 1 1 d . . . . .
C2 C 0.6754(7) 0.44379(11) 0.4822(3) 0.0213(5) Uani 1 1 d . . . . .
H2 H 0.764719 0.447243 0.368445 0.026 Uiso 1 1 calc R . . . .
C16 C 0.4913(8) 0.63634(11) 0.5237(4) 0.0268(6) Uani 1 1 d . . . . .
H16 H 0.403818 0.644841 0.634768 0.032 Uiso 1 1 calc R . . . .
C10 C 0.4925(7) 0.54103(11) 0.6138(4) 0.0212(6) Uani 1 1 d . . . . .
C9 C 0.3548(7) 0.54586(11) 0.7832(4) 0.0236(6) Uani 1 1 d . . . . .
H9 H 0.289759 0.577458 0.834601 0.028 Uiso 1 1 calc R . . . .
C6 C 0.2595(8) 0.41537(13) 1.0390(4) 0.0280(6) Uani 1 1 d . . . . .
H6 H 0.189587 0.399175 1.144433 0.034 Uiso 1 1 calc R . . . .
C8 C 0.3287(7) 0.49517(12) 0.8656(4) 0.0232(6) Uani 1 1 d . . . . .
C4 C 0.4936(7) 0.40782(11) 0.7470(4) 0.0223(6) Uani 1 1 d . . . . .
C14 C 0.6860(7) 0.66540(11) 0.2327(4) 0.0270(6) Uani 1 1 d . . . . .
C5 C 0.3889(7) 0.38373(12) 0.9057(4) 0.0249(6) Uani 1 1 d . . . . .
H5 H 0.405394 0.347355 0.921853 0.030 Uiso 1 1 calc R . . . .
C7 C 0.2284(8) 0.47064(13) 1.0230(4) 0.0268(6) Uani 1 1 d . . . . .
H7 H 0.142277 0.490298 1.116336 0.032 Uiso 1 1 calc R . . . .
C15 C 0.5510(8) 0.67608(12) 0.3995(4) 0.0293(6) Uani 1 1 d . . . . .
H15 H 0.499820 0.710779 0.428090 0.035 Uiso 1 1 calc R . . . .
C19 C 0.9282(9) 0.29016(12) 0.2907(4) 0.0335(7) Uani 1 1 d . . . . .
H19A H 1.009776 0.293129 0.170172 0.050 Uiso 1 1 calc GR . . . .
H19B H 0.729126 0.267752 0.279771 0.050 Uiso 1 1 calc GR . . . .
H19C H 1.105474 0.275228 0.380048 0.050 Uiso 1 1 calc GR . . . .
C17 C 0.7543(9) 0.70925(13) 0.1005(5) 0.0358(7) Uani 1 1 d . . . . .
H17A H 0.930284 0.732014 0.161310 0.054 Uiso 1 1 calc GR . . . .
H17B H 0.547281 0.729178 0.066862 0.054 Uiso 1 1 calc GR . . . .
H17C H 0.828905 0.694517 -0.011137 0.054 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 C18 1.353(3) . ?
O2 C19 1.441(3) . ?
O1 C18 1.218(3) . ?
N1 C1 1.366(3) . ?
N1 C8 1.367(3) . ?
N1 C4 1.364(4) . ?
C11 C12 1.392(4) . ?
C11 C16 1.399(4) . ?
C11 C10 1.463(4) . ?
C12 C13 1.386(4) . ?
C1 C2 1.409(4) . ?
C1 C10 1.448(4) . ?
C18 C3 1.448(4) . ?
C13 C14 1.396(4) . ?
C3 C2 1.408(4) . ?
C3 C4 1.424(4) . ?
C16 C15 1.382(4) . ?
C10 C9 1.393(4) . ?
C9 C8 1.422(4) . ?
C6 C5 1.390(4) . ?
C6 C7 1.409(4) . ?
C8 C7 1.386(4) . ?
C4 C5 1.396(4) . ?
C14 C15 1.392(4) . ?
C14 C17 1.505(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
C18 O2 C19 115.5(2) . . ?
C1 N1 C8 114.2(2) . . ?
C4 N1 C1 114.9(2) . . ?
C4 N1 C8 130.9(2) . . ?
C12 C11 C16 117.4(3) . . ?
C12 C11 C10 121.0(2) . . ?
C16 C11 C10 121.6(2) . . ?
C13 C12 C11 121.4(3) . . ?
N1 C1 C2 104.5(2) . . ?
N1 C1 C10 104.8(2) . . ?
C2 C1 C10 150.7(3) . . ?
O2 C18 C3 112.5(2) . . ?
O1 C18 O2 122.5(3) . . ?
O1 C18 C3 125.0(2) . . ?
C12 C13 C14 121.2(3) . . ?
C2 C3 C18 128.3(2) . . ?
C2 C3 C4 108.3(2) . . ?
C4 C3 C18 123.4(2) . . ?
C3 C2 C1 108.4(2) . . ?
C15 C16 C11 121.1(3) . . ?
C1 C10 C11 125.9(2) . . ?
C9 C10 C11 127.2(2) . . ?
C9 C10 C1 106.9(2) . . ?
C10 C9 C8 109.7(2) . . ?
C5 C6 C7 123.5(3) . . ?
N1 C8 C9 104.3(2) . . ?
N1 C8 C7 114.0(3) . . ?
C7 C8 C9 141.7(3) . . ?
N1 C4 C3 103.9(2) . . ?
N1 C4 C5 114.3(3) . . ?
C5 C4 C3 141.8(3) . . ?
C13 C14 C17 121.8(3) . . ?
C15 C14 C13 117.4(3) . . ?
C15 C14 C17 120.9(3) . . ?
C6 C5 C4 118.5(3) . . ?
C8 C7 C6 118.7(3) . . ?
C16 C15 C14 121.5(3) . . ?


_olex2_date_sample_data_collection 2019-03-06
_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 3.457
_oxdiff_exptl_absorpt_empirical_full_min 0.687
