# 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_1903141657_0m
_database_code_depnum_ccdc_archive 'CCDC 1906199'
loop_
_audit_author_name
_audit_author_address
'Bo Xu'
;Donghua University
China
;
_audit_update_record             
;
2019-03-28 deposited with the CCDC.	2019-06-25 downloaded from the CCDC.
;
_audit_creation_date             2019-03-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19 N O2'
_chemical_formula_sum            'C22 H19 N O2'
_chemical_formula_weight         329.38
_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 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.4902(2)
_cell_length_b                   9.6989(2)
_cell_length_c                   15.4453(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.1890(10)
_cell_angle_gamma                90
_cell_volume                     1720.89(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.928
_cell_measurement_theta_min      4.133
_shelx_estimated_absorpt_T_max   0.960
_shelx_estimated_absorpt_T_min   0.941
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1396 before and 0.0558 after correction. The Ratio of minimum to maximum transmission is 0.8498. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18579
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.903
_diffrn_reflns_theta_min         4.131
_diffrn_ambient_temperature      169.98
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2855
_reflns_number_total             3262
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 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         0.205
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.059
_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)+(0.0391P)²+0.6549P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0964
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11),
 C14(H14), C17(H17), C18(H18), C20(H20), C21(H21)
2.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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
O1 O 0.34944(8) 0.59056(9) 0.78876(6) 0.0276(2) Uani 1 1 d . . . . .
O2 O 0.80248(9) 0.79662(10) 0.99579(6) 0.0335(3) Uani 1 1 d . . . . .
N1 N 0.28297(9) 0.34654(11) 0.71669(7) 0.0234(3) Uani 1 1 d . . . . .
H1A H 0.256281 0.427474 0.732683 0.028 Uiso 1 1 calc R . . . .
H1B H 0.234551 0.283011 0.697021 0.028 Uiso 1 1 calc R . . . .
C1 C 0.26042(12) 0.13414(14) 0.50177(9) 0.0275(3) Uani 1 1 d . . . . .
H1 H 0.229197 0.048198 0.519503 0.033 Uiso 1 1 calc R . . . .
C2 C 0.20966(13) 0.20351(16) 0.43216(9) 0.0335(3) Uani 1 1 d . . . . .
H2 H 0.143141 0.165778 0.403316 0.040 Uiso 1 1 calc R . . . .
C3 C 0.25529(13) 0.32683(16) 0.40470(9) 0.0334(3) Uani 1 1 d . . . . .
H3 H 0.219817 0.374774 0.357448 0.040 Uiso 1 1 calc R . . . .
C4 C 0.35310(13) 0.38075(15) 0.44621(9) 0.0326(3) Uani 1 1 d . . . . .
H4 H 0.386128 0.464485 0.426354 0.039 Uiso 1 1 calc R . . . .
C5 C 0.40287(12) 0.31274(14) 0.51666(9) 0.0274(3) Uani 1 1 d . . . . .
H5 H 0.469336 0.350952 0.545319 0.033 Uiso 1 1 calc R . . . .
C6 C 0.35642(11) 0.18882(13) 0.54590(8) 0.0223(3) Uani 1 1 d . . . . .
C7 C 0.41042(11) 0.11388(13) 0.62018(8) 0.0214(3) Uani 1 1 d . . . . .
C8 C 0.44307(12) -0.02381(14) 0.60949(9) 0.0265(3) Uani 1 1 d . . . . .
H8 H 0.426083 -0.068330 0.555920 0.032 Uiso 1 1 calc R . . . .
C9 C 0.49939(12) -0.09691(14) 0.67471(9) 0.0306(3) Uani 1 1 d . . . . .
H9 H 0.520884 -0.190310 0.665666 0.037 Uiso 1 1 calc R . . . .
C10 C 0.52441(12) -0.03366(14) 0.75332(9) 0.0299(3) Uani 1 1 d . . . . .
H10 H 0.564316 -0.082744 0.798119 0.036 Uiso 1 1 calc R . . . .
C11 C 0.49068(12) 0.10190(14) 0.76597(9) 0.0253(3) Uani 1 1 d . . . . .
H11 H 0.506561 0.144631 0.820287 0.030 Uiso 1 1 calc R . . . .
C12 C 0.43400(11) 0.17686(13) 0.70075(8) 0.0208(3) Uani 1 1 d . . . . .
C13 C 0.39667(11) 0.32018(13) 0.72225(8) 0.0205(3) Uani 1 1 d . . . . .
C14 C 0.47898(11) 0.41340(13) 0.75226(8) 0.0223(3) Uani 1 1 d . . . . .
H14 H 0.558825 0.389927 0.747261 0.027 Uiso 1 1 calc R . . . .
C15 C 0.45090(11) 0.54296(13) 0.79036(8) 0.0216(3) Uani 1 1 d . . . . .
C16 C 0.54451(11) 0.61826(13) 0.83977(8) 0.0218(3) Uani 1 1 d . . . . .
C17 C 0.51341(12) 0.69909(14) 0.90972(9) 0.0281(3) Uani 1 1 d . . . . .
H17 H 0.433234 0.712506 0.920991 0.034 Uiso 1 1 calc R . . . .
C18 C 0.59619(12) 0.76081(15) 0.96362(9) 0.0297(3) Uani 1 1 d . . . . .
H18 H 0.572858 0.813484 1.012129 0.036 Uiso 1 1 calc R . . . .
C19 C 0.71340(12) 0.74495(13) 0.94610(8) 0.0253(3) Uani 1 1 d . . . . .
C20 C 0.74607(12) 0.67014(14) 0.87379(9) 0.0276(3) Uani 1 1 d . . . . .
H20 H 0.825953 0.663165 0.859731 0.033 Uiso 1 1 calc R . . . .
C21 C 0.66267(12) 0.60596(14) 0.82237(9) 0.0261(3) Uani 1 1 d . . . . .
H21 H 0.686177 0.552460 0.774271 0.031 Uiso 1 1 calc R . . . .
C22 C 0.77423(15) 0.85645(18) 1.07736(10) 0.0417(4) Uani 1 1 d . . . . .
H22A H 0.725001 0.937751 1.067719 0.063 Uiso 1 1 calc GR . . . .
H22B H 0.845996 0.883784 1.108168 0.063 Uiso 1 1 calc GR . . . .
H22C H 0.732338 0.788803 1.112078 0.063 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
O1 C15 1.2536(16) . ?
O2 C19 1.3621(16) . ?
O2 C22 1.4305(18) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C13 1.3323(16) . ?
C1 H1 0.9500 . ?
C1 C2 1.387(2) . ?
C1 C6 1.3898(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.377(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3940(19) . ?
C6 C7 1.4833(18) . ?
C7 C8 1.3979(18) . ?
C7 C12 1.4075(17) . ?
C8 H8 0.9500 . ?
C8 C9 1.382(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.385(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.3858(19) . ?
C11 H11 0.9500 . ?
C11 C12 1.3929(18) . ?
C12 C13 1.4941(17) . ?
C13 C14 1.3814(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.4273(18) . ?
C15 C16 1.4962(18) . ?
C16 C17 1.3876(18) . ?
C16 C21 1.3947(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.3869(19) . ?
C18 H18 0.9500 . ?
C18 C19 1.388(2) . ?
C19 C20 1.3901(19) . ?
C20 H20 0.9500 . ?
C20 C21 1.3800(19) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
C19 O2 C22 117.64(12) . . ?
H1A N1 H1B 120.0 . . ?
C13 N1 H1A 120.0 . . ?
C13 N1 H1B 120.0 . . ?
C2 C1 H1 119.6 . . ?
C2 C1 C6 120.79(13) . . ?
C6 C1 H1 119.6 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.26(14) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.74(13) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.10(14) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.68(13) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.39(12) . . ?
C1 C6 C7 120.49(12) . . ?
C5 C6 C7 121.08(12) . . ?
C8 C7 C6 119.06(11) . . ?
C8 C7 C12 118.15(12) . . ?
C12 C7 C6 122.75(11) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 C7 121.80(13) . . ?
C9 C8 H8 119.1 . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.82(12) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.36(13) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.3 . . ?
C10 C11 C12 121.41(13) . . ?
C12 C11 H11 119.3 . . ?
C7 C12 C13 123.32(11) . . ?
C11 C12 C7 119.43(12) . . ?
C11 C12 C13 117.19(11) . . ?
N1 C13 C12 116.73(11) . . ?
N1 C13 C14 124.03(12) . . ?
C14 C13 C12 119.06(11) . . ?
C13 C14 H14 118.1 . . ?
C13 C14 C15 123.75(12) . . ?
C15 C14 H14 118.1 . . ?
O1 C15 C14 122.29(12) . . ?
O1 C15 C16 119.25(11) . . ?
C14 C15 C16 118.28(11) . . ?
C17 C16 C15 118.61(12) . . ?
C17 C16 C21 117.76(12) . . ?
C21 C16 C15 123.53(11) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 C16 121.79(13) . . ?
C18 C17 H17 119.1 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.43(13) . . ?
C19 C18 H18 120.3 . . ?
O2 C19 C18 124.77(12) . . ?
O2 C19 C20 115.63(12) . . ?
C18 C19 C20 119.60(12) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.13(13) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 H21 119.4 . . ?
C20 C21 C16 121.17(12) . . ?
C20 C21 H21 119.4 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.88 2.09 2.7182(14) 127.8 .

_olex2_submission_special_instructions 'No special instructions were received'
