# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_cz-2_pl
_database_code_depnum_ccdc_archive 'CCDC 2050872'
loop_
_audit_author_name
_audit_author_address
Tulianjing
;Institute of Molecular Aggregation Science, Tianjin University
China
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-07-18 downloaded from the CCDC.
;
_audit_creation_date             2020-12-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H11 N O'
_chemical_formula_sum            'C14 H11 N O'
_chemical_formula_weight         209.24
_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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   17.5197(5)
_cell_length_b                   4.36700(10)
_cell_length_c                   55.732(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.514(3)
_cell_angle_gamma                90
_cell_volume                     4262.5(2)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    8074
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.0430
_cell_measurement_theta_min      4.6160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       66
_diffrn_reflns_limit_l_min       -65
_diffrn_reflns_number            13702
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.097
_diffrn_reflns_theta_max         67.097
_diffrn_reflns_theta_min         4.762
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3388
_reflns_number_total             3810
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3810
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.062
_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)+(0.0608P)²+0.8701P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1204
_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:
 C01E(H01E), C01F(H01F), C01N(H01N), C01X(H01X), C01Z(H01Z), C02D(H02D),
 C02I(H02I), C02X(H02X), C02A(H02A), C02H(H02H), C02L(H02L), C02N(H02N),
 C02U(H02U), C035(H035), C03C(H03D), C03K(H03K)
2.b Idealised Me refined as rotating group:
 C03F(H03A,H03B,H03C), C03I(H03E,H03F,H03G)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O009 O 0.64309(8) 0.2123(4) -0.11301(2) 0.1045(5) Uani 1 1 d . . . . .
N006 N 0.56166(6) 0.3169(3) -0.08357(2) 0.0566(3) Uani 1 1 d . . . . .
C00K C 0.49711(7) 0.4549(3) -0.07256(2) 0.0535(3) Uani 1 1 d . . . . .
C00O C 0.60251(7) 0.1521(3) -0.06536(3) 0.0564(3) Uani 1 1 d . . . . .
C00R C 0.49874(7) 0.3754(3) -0.04833(2) 0.0533(3) Uani 1 1 d . . . . .
C00S C 0.56532(7) 0.1870(3) -0.04375(2) 0.0550(3) Uani 1 1 d . . . . .
C01E C 0.59435(9) 0.0503(3) -0.02293(3) 0.0668(4) Uani 1 1 d . . . . .
H01E H 0.569770 0.074077 -0.008459 0.080 Uiso 1 1 calc R . . . .
C01F C 0.44207(8) 0.4763(3) -0.03327(3) 0.0620(3) Uani 1 1 d . . . . .
H01F H 0.443349 0.423567 -0.017093 0.074 Uiso 1 1 calc R . . . .
C01J C 0.58552(9) 0.3413(4) -0.10702(3) 0.0678(4) Uani 1 1 d . . . . .
C01N C 0.43859(9) 0.6367(4) -0.08198(3) 0.0680(4) Uani 1 1 d . . . . .
H01N H 0.436921 0.691596 -0.098105 0.082 Uiso 1 1 calc R . . . .
C01X C 0.38400(8) 0.6555(4) -0.04265(3) 0.0690(4) Uani 1 1 d . . . . .
H01X H 0.345476 0.723981 -0.032813 0.083 Uiso 1 1 calc R . . . .
C01Z C 0.66880(8) -0.0227(4) -0.06659(3) 0.0707(4) Uani 1 1 d . . . . .
H01Z H 0.693596 -0.048584 -0.081000 0.085 Uiso 1 1 calc R . . . .
C02D C 0.38287(9) 0.7335(4) -0.06657(3) 0.0734(4) Uani 1 1 d . . . . .
H02D H 0.343286 0.855479 -0.072593 0.088 Uiso 1 1 calc R . . . .
C02I C 0.66019(9) -0.1211(4) -0.02409(3) 0.0783(4) Uani 1 1 d . . . . .
H02I H 0.680350 -0.213502 -0.010291 0.094 Uiso 1 1 calc R . . . .
C02X C 0.69639(9) -0.1564(4) -0.04560(4) 0.0800(5) Uani 1 1 d . . . . .
H02X H 0.740663 -0.273637 -0.045998 0.096 Uiso 1 1 calc R . . . .
C03F C 0.54050(11) 0.5254(5) -0.12462(3) 0.0924(6) Uani 1 1 d . . . . .
H03A H 0.536823 0.732444 -0.118969 0.139 Uiso 1 1 calc GR . . . .
H03B H 0.490222 0.439915 -0.126523 0.139 Uiso 1 1 calc GR . . . .
H03C H 0.565238 0.523376 -0.139783 0.139 Uiso 1 1 calc GR . . . .
O00B O -0.10779(8) 0.0114(4) -0.13541(2) 0.1090(5) Uani 1 1 d . . . . .
N003 N -0.16661(6) -0.2310(3) -0.16621(2) 0.0565(3) Uani 1 1 d . . . . .
C00Q C -0.11817(8) -0.1111(3) -0.18412(2) 0.0583(3) Uani 1 1 d . . . . .
C00W C -0.21168(8) -0.3969(3) -0.20278(2) 0.0587(3) Uani 1 1 d . . . . .
C016 C -0.22416(7) -0.4086(3) -0.17813(2) 0.0547(3) Uani 1 1 d . . . . .
C01B C -0.14485(8) -0.2115(3) -0.20650(2) 0.0598(3) Uani 1 1 d . . . . .
C01Y C -0.15867(9) -0.1586(4) -0.14209(3) 0.0679(4) Uani 1 1 d . . . . .
C02A C -0.28510(9) -0.5751(4) -0.16942(3) 0.0694(4) Uani 1 1 d . . . . .
H02A H -0.293396 -0.588091 -0.153039 0.083 Uiso 1 1 calc R . . . .
C02H C -0.26073(10) -0.5456(4) -0.21887(3) 0.0755(4) Uani 1 1 d . . . . .
H02H H -0.252501 -0.537001 -0.235272 0.091 Uiso 1 1 calc R . . . .
C02L C -0.05402(9) 0.0759(4) -0.18197(3) 0.0753(4) Uani 1 1 d . . . . .
H02L H -0.035966 0.143424 -0.167048 0.090 Uiso 1 1 calc R . . . .
C02N C -0.10711(11) -0.1268(4) -0.22712(3) 0.0775(5) Uani 1 1 d . . . . .
H02N H -0.124405 -0.194087 -0.242130 0.093 Uiso 1 1 calc R . . . .
C02U C -0.33307(10) -0.7209(4) -0.18593(4) 0.0823(5) Uani 1 1 d . . . . .
H02U H -0.374292 -0.832520 -0.180418 0.099 Uiso 1 1 calc R . . . .
C035 C -0.01820(11) 0.1576(4) -0.20276(4) 0.0881(5) Uani 1 1 d . . . . .
H035 H 0.024550 0.283590 -0.201741 0.106 Uiso 1 1 calc R . . . .
C03C C -0.04379(11) 0.0583(4) -0.22493(4) 0.0893(6) Uani 1 1 d . . . . .
H03D H -0.018078 0.116731 -0.238576 0.107 Uiso 1 1 calc R . . . .
C03I C -0.21206(11) -0.2872(5) -0.12463(3) 0.0874(5) Uani 1 1 d . . . . .
H03E H -0.196539 -0.225496 -0.108707 0.131 Uiso 1 1 calc GR . . . .
H03F H -0.211623 -0.506595 -0.125673 0.131 Uiso 1 1 calc GR . . . .
H03G H -0.262686 -0.212958 -0.128182 0.131 Uiso 1 1 calc GR . . . .
C03K C -0.32164(11) -0.7059(4) -0.21023(4) 0.0857(5) Uani 1 1 d . . . . .
H03K H -0.355275 -0.804617 -0.220854 0.103 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O009 C01J 1.2100(19) . ?
N006 C00K 1.4337(16) . ?
N006 C00O 1.4220(18) . ?
N006 C01J 1.3863(18) . ?
C00K C00R 1.3941(19) . ?
C00K C01N 1.389(2) . ?
C00O C00S 1.3930(19) . ?
C00O C01Z 1.393(2) . ?
C00R C00S 1.4449(19) . ?
C00R C01F 1.3887(19) . ?
C00S C01E 1.389(2) . ?
C01E C02I 1.378(2) . ?
C01F C01X 1.376(2) . ?
C01J C03F 1.480(2) . ?
C01N C02D 1.383(2) . ?
C01X C02D 1.376(2) . ?
C01Z C02X 1.383(2) . ?
C02I C02X 1.379(3) . ?
O00B C01Y 1.211(2) . ?
N003 C00Q 1.4267(18) . ?
N003 C016 1.4227(17) . ?
N003 C01Y 1.3845(18) . ?
C00Q C01B 1.391(2) . ?
C00Q C02L 1.392(2) . ?
C00W C016 1.3979(19) . ?
C00W C01B 1.443(2) . ?
C00W C02H 1.387(2) . ?
C016 C02A 1.390(2) . ?
C01B C02N 1.391(2) . ?
C01Y C03I 1.478(2) . ?
C02A C02U 1.385(2) . ?
C02H C03K 1.374(3) . ?
C02L C035 1.379(3) . ?
C02N C03C 1.375(3) . ?
C02U C03K 1.376(3) . ?
C035 C03C 1.373(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
C00O N006 C00K 107.16(11) . . ?
C01J N006 C00K 129.20(12) . . ?
C01J N006 C00O 123.57(12) . . ?
C00R C00K N006 108.29(11) . . ?
C01N C00K N006 131.42(13) . . ?
C01N C00K C00R 120.29(12) . . ?
C00S C00O N006 108.90(11) . . ?
C00S C00O C01Z 120.80(14) . . ?
C01Z C00O N006 130.30(14) . . ?
C00K C00R C00S 107.99(11) . . ?
C01F C00R C00K 120.66(13) . . ?
C01F C00R C00S 131.35(13) . . ?
C00O C00S C00R 107.65(12) . . ?
C01E C00S C00O 120.40(13) . . ?
C01E C00S C00R 131.94(13) . . ?
C02I C01E C00S 118.85(15) . . ?
C01X C01F C00R 118.95(14) . . ?
O009 C01J N006 119.92(15) . . ?
O009 C01J C03F 120.22(14) . . ?
N006 C01J C03F 119.85(13) . . ?
C02D C01N C00K 117.80(14) . . ?
C02D C01X C01F 120.05(14) . . ?
C02X C01Z C00O 117.58(16) . . ?
C01X C02D C01N 122.25(14) . . ?
C01E C02I C02X 120.42(15) . . ?
C02I C02X C01Z 121.95(15) . . ?
C016 N003 C00Q 107.51(11) . . ?
C01Y N003 C00Q 123.30(12) . . ?
C01Y N003 C016 129.02(12) . . ?
C01B C00Q N003 108.63(12) . . ?
C01B C00Q C02L 120.91(14) . . ?
C02L C00Q N003 130.46(14) . . ?
C016 C00W C01B 108.08(12) . . ?
C02H C00W C016 120.51(15) . . ?
C02H C00W C01B 131.40(14) . . ?
C00W C016 N003 108.14(12) . . ?
C02A C016 N003 131.59(13) . . ?
C02A C016 C00W 120.27(13) . . ?
C00Q C01B C00W 107.63(12) . . ?
C02N C01B C00Q 120.05(15) . . ?
C02N C01B C00W 132.31(15) . . ?
O00B C01Y N003 119.54(15) . . ?
O00B C01Y C03I 120.25(14) . . ?
N003 C01Y C03I 120.21(14) . . ?
C02U C02A C016 117.84(15) . . ?
C03K C02H C00W 119.08(16) . . ?
C035 C02L C00Q 117.62(17) . . ?
C03C C02N C01B 118.88(17) . . ?
C03K C02U C02A 122.04(17) . . ?
C03C C035 C02L 121.95(18) . . ?
C035 C03C C02N 120.58(17) . . ?
C02H C03K C02U 120.24(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N006 C00K C00R C00S 0.49(14) . . . . ?
N006 C00K C00R C01F -179.39(11) . . . . ?
N006 C00K C01N C02D 179.15(13) . . . . ?
N006 C00O C00S C00R 0.65(14) . . . . ?
N006 C00O C00S C01E -179.30(11) . . . . ?
N006 C00O C01Z C02X 179.39(14) . . . . ?
C00K N006 C00O C00S -0.35(13) . . . . ?
C00K N006 C00O C01Z 179.59(14) . . . . ?
C00K N006 C01J O009 178.30(15) . . . . ?
C00K N006 C01J C03F -1.6(2) . . . . ?
C00K C00R C00S C00O -0.71(14) . . . . ?
C00K C00R C00S C01E 179.23(13) . . . . ?
C00K C00R C01F C01X 0.2(2) . . . . ?
C00K C01N C02D C01X 0.0(2) . . . . ?
C00O N006 C00K C00R -0.09(13) . . . . ?
C00O N006 C00K C01N -179.43(14) . . . . ?
C00O N006 C01J O009 1.8(2) . . . . ?
C00O N006 C01J C03F -178.18(15) . . . . ?
C00O C00S C01E C02I -0.3(2) . . . . ?
C00O C01Z C02X C02I 0.2(3) . . . . ?
C00R C00K C01N C02D -0.1(2) . . . . ?
C00R C00S C01E C02I 179.75(13) . . . . ?
C00R C01F C01X C02D -0.3(2) . . . . ?
C00S C00O C01Z C02X -0.7(2) . . . . ?
C00S C00R C01F C01X -179.64(13) . . . . ?
C00S C01E C02I C02X -0.2(2) . . . . ?
C01E C02I C02X C01Z 0.2(3) . . . . ?
C01F C00R C00S C00O 179.15(13) . . . . ?
C01F C00R C00S C01E -0.9(2) . . . . ?
C01F C01X C02D C01N 0.3(3) . . . . ?
C01J N006 C00K C00R -177.08(13) . . . . ?
C01J N006 C00K C01N 3.6(2) . . . . ?
C01J N006 C00O C00S 176.84(12) . . . . ?
C01J N006 C00O C01Z -3.2(2) . . . . ?
C01N C00K C00R C00S 179.91(12) . . . . ?
C01N C00K C00R C01F 0.03(19) . . . . ?
C01Z C00O C00S C00R -179.30(12) . . . . ?
C01Z C00O C00S C01E 0.8(2) . . . . ?
N003 C00Q C01B C00W 0.37(14) . . . . ?
N003 C00Q C01B C02N -179.74(12) . . . . ?
N003 C00Q C02L C035 -179.80(14) . . . . ?
N003 C016 C02A C02U 178.53(13) . . . . ?
C00Q N003 C016 C00W -0.32(14) . . . . ?
C00Q N003 C016 C02A 179.82(14) . . . . ?
C00Q N003 C01Y O00B -1.1(2) . . . . ?
C00Q N003 C01Y C03I 178.78(14) . . . . ?
C00Q C01B C02N C03C -0.4(2) . . . . ?
C00Q C02L C035 C03C -0.4(3) . . . . ?
C00W C016 C02A C02U -1.3(2) . . . . ?
C00W C01B C02N C03C 179.44(14) . . . . ?
C00W C02H C03K C02U -0.8(2) . . . . ?
C016 N003 C00Q C01B -0.04(14) . . . . ?
C016 N003 C00Q C02L 179.84(14) . . . . ?
C016 N003 C01Y O00B -175.85(15) . . . . ?
C016 N003 C01Y C03I 4.0(2) . . . . ?
C016 C00W C01B C00Q -0.57(14) . . . . ?
C016 C00W C01B C02N 179.56(15) . . . . ?
C016 C00W C02H C03K -0.3(2) . . . . ?
C016 C02A C02U C03K 0.3(3) . . . . ?
C01B C00Q C02L C035 0.1(2) . . . . ?
C01B C00W C016 N003 0.54(14) . . . . ?
C01B C00W C016 C02A -179.57(12) . . . . ?
C01B C00W C02H C03K -179.13(14) . . . . ?
C01B C02N C03C C035 0.1(3) . . . . ?
C01Y N003 C00Q C01B -175.79(12) . . . . ?
C01Y N003 C00Q C02L 4.1(2) . . . . ?
C01Y N003 C016 C00W 175.12(13) . . . . ?
C01Y N003 C016 C02A -4.7(2) . . . . ?
C02A C02U C03K C02H 0.7(3) . . . . ?
C02H C00W C016 N003 -178.57(12) . . . . ?
C02H C00W C016 C02A 1.3(2) . . . . ?
C02H C00W C01B C00Q 178.41(14) . . . . ?
C02H C00W C01B C02N -1.5(3) . . . . ?
C02L C00Q C01B C00W -179.52(12) . . . . ?
C02L C00Q C01B C02N 0.4(2) . . . . ?
C02L C035 C03C C02N 0.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cz-9-real
_database_code_depnum_ccdc_archive 'CCDC 2050879'
loop_
_audit_author_name
_audit_author_address
Tulianjing
;Institute of Molecular Aggregation Science, Tianjin University
China
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-07-18 downloaded from the CCDC.
;
_audit_creation_date             2020-12-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H25 N O'
_chemical_formula_sum            'C21 H22 N O'
_chemical_formula_weight         304.39
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H22ON
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   5.75490(10)
_cell_length_b                   32.9565(7)
_cell_length_c                   9.1902(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1743.03(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5391
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.9040
_cell_measurement_theta_min      4.9880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.546
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9713
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.535
_diffrn_reflns_theta_min         4.996
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -20.00   1.00    2.69    --  -41.37 -37.00  30.00   96
  2  ω   -113.00 -21.00   1.00    2.69    --  -41.37 -37.00 120.00   92
  3  ω   -112.00 -82.00   1.00    2.69    --  -41.37-134.00-156.00   30
  4  ω      5.00  50.00   1.00    2.69    --   41.37 -99.00 -90.00   45
  5  ω     27.00  54.00   1.00    2.69    --   41.37-125.00-180.00   27
  6  ω     47.00  94.00   1.00    2.69    --   41.37-135.00  23.00   47
  7  ω     74.00 100.00   1.00   10.73    --  105.32 -94.00-120.00   26
  8  ω     33.00 113.00   1.00   10.73    --  105.32 -45.00 150.00   80
  9  ω    130.00 178.00   1.00   10.73    --  105.32  61.00  60.00   48
 10  ω     74.00 103.00   1.00   10.73    --  105.32 -94.00  60.00   29
 11  ω     31.00  70.00   1.00   10.73    --  105.32 -94.00  60.00   39
 12  ω     77.00 177.00   1.00   10.73    --  105.32  30.00-180.00  100
 13  ω    134.00 172.00   1.00   10.73    --  105.32 125.00  60.00   38
 14  ω     24.00  72.00   1.00   10.73    --  105.32 -15.00   0.00   48
 15  ω    133.00 169.00   1.00   10.73    --  105.32  77.00  90.00   36
 16  ω     75.00 115.00   1.00   10.73    --  105.32 -15.00   0.00   40
 17  ω     29.00 122.00   1.00   10.73    --  105.32 -77.00  90.00   93
 18  ω     97.00 124.00   1.00   10.73    --  105.32 125.00-180.00   27
 19  ω    108.00 178.00   1.00   10.73    --  105.32 125.00 120.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0028338000
_diffrn_orient_matrix_UB_12      0.1396679000
_diffrn_orient_matrix_UB_13      -0.0258915000
_diffrn_orient_matrix_UB_21      0.0026741000
_diffrn_orient_matrix_UB_22      -0.0928655000
_diffrn_orient_matrix_UB_23      -0.0388936000
_diffrn_orient_matrix_UB_31      -0.2676173000
_diffrn_orient_matrix_UB_32      -0.0023947000
_diffrn_orient_matrix_UB_33      -0.0001327000
_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         0.785
_reflns_Friedel_fraction_full    0.925
_reflns_Friedel_fraction_max     0.870
_reflns_number_gt                2925
_reflns_number_total             3252
_reflns_odcompleteness_completeness 99.89
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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         0.116
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Flack x determined using 1178 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3252
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      1.055
_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)+(0.0592P)²+0.0269P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0979
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C007(H00A,H00B), C009(H00C,H00D), C00D(H00H,H00I), C00E(H00J,H00K), C00F(H00L,
 H00M), C00H(H00O,H00P), C00L(H00T,H00U)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00E), C00B(H00F), C00C(H00G), C00G(H00N), C00I(H00Q), C00J(H00R),
 C00K(H00S), C00N(H00Y)
2.c Idealised Me refined as rotating group:
 C00M(H00V,H00W,H00X)
;
_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
N001 N 1.0141(3) 0.64830(5) 0.4180(2) 0.0484(4) Uani 1 1 d . . . . .
O002 O 0.8942(3) 0.61386(7) 0.2190(2) 0.0818(6) Uani 1 1 d . . . . .
C003 C 1.2012(3) 0.66794(6) 0.3457(3) 0.0482(4) Uani 1 1 d . . . . .
C004 C 0.8689(3) 0.62014(6) 0.3473(3) 0.0528(5) Uani 1 1 d . . . . .
C005 C 1.2035(3) 0.68810(5) 0.5847(3) 0.0500(5) Uani 1 1 d . . . . .
C006 C 1.0143(3) 0.66139(6) 0.5651(3) 0.0490(4) Uani 1 1 d . . . . .
C007 C 0.5492(4) 0.56804(6) 0.3450(3) 0.0554(5) Uani 1 1 d . . . . .
H00A H 0.467166 0.582385 0.268487 0.066 Uiso 1 1 calc R . . . .
H00B H 0.655356 0.549057 0.299301 0.066 Uiso 1 1 calc R . . . .
C008 C 1.3214(3) 0.69174(6) 0.4478(3) 0.0505(5) Uani 1 1 d . . . . .
C009 C 0.6874(3) 0.59828(6) 0.4347(3) 0.0516(5) Uani 1 1 d . . . . .
H00C H 0.581612 0.618037 0.476311 0.062 Uiso 1 1 calc R . . . .
H00D H 0.762404 0.584081 0.514316 0.062 Uiso 1 1 calc R . . . .
C00A C 1.2728(4) 0.66633(7) 0.2022(3) 0.0608(6) Uani 1 1 d . . . . .
H00E H 1.193612 0.650725 0.134019 0.073 Uiso 1 1 calc R . . . .
C00B C 1.2422(4) 0.70645(7) 0.7195(3) 0.0620(6) Uani 1 1 d . . . . .
H00F H 1.367152 0.724015 0.731889 0.074 Uiso 1 1 calc R . . . .
C00C C 1.4667(4) 0.68880(8) 0.1636(3) 0.0696(7) Uani 1 1 d . . . . .
H00G H 1.516582 0.688359 0.067313 0.084 Uiso 1 1 calc R . . . .
C00D C 0.0668(4) 0.48949(7) 0.4399(3) 0.0582(5) Uani 1 1 d . . . . .
H00H H -0.032733 0.507360 0.496023 0.070 Uiso 1 1 calc R . . . .
H00I H 0.158748 0.473780 0.508136 0.070 Uiso 1 1 calc R . . . .
C00E C 0.2292(4) 0.51515(6) 0.3483(3) 0.0568(5) Uani 1 1 d . . . . .
H00J H 0.137902 0.530357 0.278281 0.068 Uiso 1 1 calc R . . . .
H00K H 0.332047 0.497344 0.294287 0.068 Uiso 1 1 calc R . . . .
C00F C 0.3752(3) 0.54467(6) 0.4366(3) 0.0570(5) Uani 1 1 d . . . . .
H00L H 0.272941 0.563785 0.484920 0.068 Uiso 1 1 calc R . . . .
H00M H 0.458246 0.529721 0.511172 0.068 Uiso 1 1 calc R . . . .
C00G C 1.5889(4) 0.71192(8) 0.2638(3) 0.0695(7) Uani 1 1 d . . . . .
H00N H 1.719722 0.726321 0.234434 0.083 Uiso 1 1 calc R . . . .
C00H C -0.0853(4) 0.46059(7) 0.3525(3) 0.0575(5) Uani 1 1 d . . . . .
H00O H -0.173695 0.476081 0.281847 0.069 Uiso 1 1 calc R . . . .
H00P H 0.013550 0.441897 0.299413 0.069 Uiso 1 1 calc R . . . .
C00I C 1.5180(4) 0.71365(6) 0.4056(4) 0.0626(6) Uani 1 1 d . . . . .
H00Q H 1.599462 0.729174 0.472991 0.075 Uiso 1 1 calc R . . . .
C00J C 0.8672(4) 0.65349(8) 0.6813(3) 0.0628(6) Uani 1 1 d . . . . .
H00R H 0.741180 0.636092 0.670186 0.075 Uiso 1 1 calc R . . . .
C00K C 1.0956(5) 0.69851(8) 0.8332(3) 0.0686(6) Uani 1 1 d . . . . .
H00S H 1.119519 0.710849 0.922936 0.082 Uiso 1 1 calc R . . . .
C00L C -0.2520(4) 0.43650(8) 0.4466(3) 0.0697(7) Uani 1 1 d . . . . .
H00T H -0.347685 0.455237 0.501672 0.084 Uiso 1 1 calc R . . . .
H00U H -0.163180 0.420498 0.515503 0.084 Uiso 1 1 calc R . . . .
C00M C -0.4094(5) 0.40834(8) 0.3602(4) 0.0785(8) Uani 1 1 d . . . . .
H00V H -0.496172 0.423864 0.290450 0.118 Uiso 1 1 calc GR . . . .
H00W H -0.514667 0.394862 0.425162 0.118 Uiso 1 1 calc GR . . . .
H00X H -0.316581 0.388528 0.310289 0.118 Uiso 1 1 calc GR . . . .
C00N C 0.9106(5) 0.67187(8) 0.8139(3) 0.0703(7) Uani 1 1 d . . . . .
H00Y H 0.813458 0.666272 0.892235 0.084 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N001 C003 1.421(3) . ?
N001 C004 1.408(3) . ?
N001 C006 1.419(3) . ?
O002 C004 1.205(3) . ?
C003 C008 1.405(3) . ?
C003 C00A 1.383(4) . ?
C004 C009 1.502(3) . ?
C005 C006 1.412(3) . ?
C005 C008 1.434(3) . ?
C005 C00B 1.396(3) . ?
C006 C00J 1.387(3) . ?
C007 H00A 0.9700 . ?
C007 H00B 0.9700 . ?
C007 C009 1.519(3) . ?
C007 C00F 1.518(3) . ?
C008 C00I 1.397(3) . ?
C009 H00C 0.9700 . ?
C009 H00D 0.9700 . ?
C00A H00E 0.9300 . ?
C00A C00C 1.385(3) . ?
C00B H00F 0.9300 . ?
C00B C00K 1.369(4) . ?
C00C H00G 0.9300 . ?
C00C C00G 1.387(4) . ?
C00D H00H 0.9700 . ?
C00D H00I 0.9700 . ?
C00D C00E 1.516(3) . ?
C00D C00H 1.523(3) . ?
C00E H00J 0.9700 . ?
C00E H00K 0.9700 . ?
C00E C00F 1.520(3) . ?
C00F H00L 0.9700 . ?
C00F H00M 0.9700 . ?
C00G H00N 0.9300 . ?
C00G C00I 1.366(4) . ?
C00H H00O 0.9700 . ?
C00H H00P 0.9700 . ?
C00H C00L 1.516(3) . ?
C00I H00Q 0.9300 . ?
C00J H00R 0.9300 . ?
C00J C00N 1.384(4) . ?
C00K H00S 0.9300 . ?
C00K C00N 1.391(4) . ?
C00L H00T 0.9700 . ?
C00L H00U 0.9700 . ?
C00L C00M 1.520(3) . ?
C00M H00V 0.9600 . ?
C00M H00W 0.9600 . ?
C00M H00X 0.9600 . ?
C00N H00Y 0.9300 . ?

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
C004 N001 C003 122.30(19) . . ?
C004 N001 C006 129.83(18) . . ?
C006 N001 C003 107.83(16) . . ?
C008 C003 N001 108.37(19) . . ?
C00A C003 N001 130.9(2) . . ?
C00A C003 C008 120.77(19) . . ?
N001 C004 C009 118.8(2) . . ?
O002 C004 N001 119.5(2) . . ?
O002 C004 C009 121.64(19) . . ?
C006 C005 C008 107.74(19) . . ?
C00B C005 C006 120.4(2) . . ?
C00B C005 C008 131.8(2) . . ?
C005 C006 N001 108.17(18) . . ?
C00J C006 N001 132.52(19) . . ?
C00J C006 C005 119.3(2) . . ?
H00A C007 H00B 107.9 . . ?
C009 C007 H00A 109.2 . . ?
C009 C007 H00B 109.2 . . ?
C00F C007 H00A 109.2 . . ?
C00F C007 H00B 109.2 . . ?
C00F C007 C009 112.19(19) . . ?
C003 C008 C005 107.84(17) . . ?
C00I C008 C003 120.1(2) . . ?
C00I C008 C005 132.0(2) . . ?
C004 C009 C007 112.88(19) . . ?
C004 C009 H00C 109.0 . . ?
C004 C009 H00D 109.0 . . ?
C007 C009 H00C 109.0 . . ?
C007 C009 H00D 109.0 . . ?
H00C C009 H00D 107.8 . . ?
C003 C00A H00E 121.2 . . ?
C003 C00A C00C 117.6(2) . . ?
C00C C00A H00E 121.2 . . ?
C005 C00B H00F 120.1 . . ?
C00K C00B C005 119.7(2) . . ?
C00K C00B H00F 120.1 . . ?
C00A C00C H00G 118.9 . . ?
C00A C00C C00G 122.1(2) . . ?
C00G C00C H00G 118.9 . . ?
H00H C00D H00I 107.6 . . ?
C00E C00D H00H 108.7 . . ?
C00E C00D H00I 108.7 . . ?
C00E C00D C00H 114.2(2) . . ?
C00H C00D H00H 108.7 . . ?
C00H C00D H00I 108.7 . . ?
C00D C00E H00J 108.8 . . ?
C00D C00E H00K 108.8 . . ?
C00D C00E C00F 113.6(2) . . ?
H00J C00E H00K 107.7 . . ?
C00F C00E H00J 108.8 . . ?
C00F C00E H00K 108.8 . . ?
C007 C00F C00E 113.2(2) . . ?
C007 C00F H00L 108.9 . . ?
C007 C00F H00M 108.9 . . ?
C00E C00F H00L 108.9 . . ?
C00E C00F H00M 108.9 . . ?
H00L C00F H00M 107.8 . . ?
C00C C00G H00N 119.8 . . ?
C00I C00G C00C 120.3(2) . . ?
C00I C00G H00N 119.8 . . ?
C00D C00H H00O 109.0 . . ?
C00D C00H H00P 109.0 . . ?
H00O C00H H00P 107.8 . . ?
C00L C00H C00D 113.0(2) . . ?
C00L C00H H00O 109.0 . . ?
C00L C00H H00P 109.0 . . ?
C008 C00I H00Q 120.5 . . ?
C00G C00I C008 119.0(2) . . ?
C00G C00I H00Q 120.5 . . ?
C006 C00J H00R 120.5 . . ?
C00N C00J C006 119.1(2) . . ?
C00N C00J H00R 120.5 . . ?
C00B C00K H00S 120.2 . . ?
C00B C00K C00N 119.7(2) . . ?
C00N C00K H00S 120.2 . . ?
C00H C00L H00T 108.9 . . ?
C00H C00L H00U 108.9 . . ?
C00H C00L C00M 113.5(2) . . ?
H00T C00L H00U 107.7 . . ?
C00M C00L H00T 108.9 . . ?
C00M C00L H00U 108.9 . . ?
C00L C00M H00V 109.5 . . ?
C00L C00M H00W 109.5 . . ?
C00L C00M H00X 109.5 . . ?
H00V C00M H00W 109.5 . . ?
H00V C00M H00X 109.5 . . ?
H00W C00M H00X 109.5 . . ?
C00J C00N C00K 121.8(3) . . ?
C00J C00N H00Y 119.1 . . ?
C00K C00N H00Y 119.1 . . ?

_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 1.544
_oxdiff_exptl_absorpt_empirical_full_min 0.473
####################################################################### 
# 
# 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_cz-8(2)
_database_code_depnum_ccdc_archive 'CCDC 2050878'
loop_
_audit_author_name
_audit_author_address
Tulianjing
;Institute of Molecular Aggregation Science, Tianjin University
China
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-07-18 downloaded from the CCDC.
;
_audit_creation_date             2020-12-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        Cz-8
_chemical_formula_moiety         'C20 H23 N O'
_chemical_formula_sum            'C20 H23 N O'
_chemical_formula_weight         293.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H23ON
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.1532(2)
_cell_length_b                   31.2312(5)
_cell_length_c                   5.75440(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.535(2)
_cell_angle_gamma                90
_cell_volume                     1644.39(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5385
_cell_measurement_temperature    298
_cell_measurement_theta_max      72.5420
_cell_measurement_theta_min      4.8090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_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    1.185
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_preparation       'solvent evaporate'
_exptl_crystal_recrystallization_method needle
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            10211
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         4.833
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00  30.00   1.00    1.99    --  -41.12  57.00 -30.00   92
  2  ω   -110.00 -14.00   1.00    1.99    --  -41.12 -57.00-180.00   96
  3  ω     37.00  86.00   1.00    1.99    --   41.12  77.00  90.00   49
  4  ω      9.00  77.00   1.00    1.99    --   41.12 -99.00  30.00   68
  5  ω    114.00 145.00   1.00    7.96    --  105.32  61.00  90.00   31
  6  ω     87.00 113.00   1.00    7.96    --  105.32-125.00  60.00   26
  7  ω     29.00 125.00   1.00    7.96    --  105.32 -77.00  60.00   96
  8  ω    124.00 177.00   1.00    7.96    --  105.32  45.00  60.00   53
  9  ω     87.00 113.00   1.00    7.96    --  105.32  61.00  90.00   26
 10  ω     24.00  56.00   1.00    7.96    --  105.32 -94.00-180.00   32
 11  ω     36.00 131.00   1.00    7.96    --  105.32 -61.00 -90.00   95
 12  ω     85.00 110.00   1.00    7.96    --  105.32  45.00  60.00   25
 13  ω    111.00 137.00   1.00    7.96    --  105.32 125.00 -90.00   26
 14  ω    104.00 130.00   1.00    7.96    --  105.32 -45.00  60.00   26
 15  ω     42.00  79.00   1.00    7.96    --  105.32 -45.00  60.00   37
 16  ω     53.00 178.00   1.00    7.96    --  105.32  15.00  30.00  125
 17  ω    117.00 178.00   1.00    7.96    --  105.32 125.00 -30.00   61
 18  ω     24.00 108.00   1.00    7.96    --  105.32 -94.00 -90.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1196206000
_diffrn_orient_matrix_UB_12      -0.0345974000
_diffrn_orient_matrix_UB_13      -0.0214274000
_diffrn_orient_matrix_UB_21      0.1164619000
_diffrn_orient_matrix_UB_22      -0.0351075000
_diffrn_orient_matrix_UB_23      0.0374992000
_diffrn_orient_matrix_UB_31      -0.0216565000
_diffrn_orient_matrix_UB_32      0.0021760000
_diffrn_orient_matrix_UB_33      0.2642807000
_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'
_diffrn_special_details          no
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2597
_reflns_number_total             2928
_reflns_odcompleteness_completeness 99.93
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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         0.128
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.026
_refine_ls_extinction_coef       0.0025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         2928
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.060
_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)+(0.0522P)²+0.1816P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1033
_refine_special_details          no
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
N001 N 0.71566(11) 0.64177(3) 0.06210(16) 0.0490(3) Uani 1 1 d . . . . .
O002 O 0.91691(12) 0.60526(4) 0.1831(2) 0.0820(4) Uani 1 1 d . . . . .
C003 C 0.56759(13) 0.65600(4) 0.0614(2) 0.0484(3) Uani 1 1 d . . . . .
C004 C 0.54626(13) 0.68429(4) -0.1257(2) 0.0492(3) Uani 1 1 d . . . . .
C005 C 0.78552(13) 0.66257(4) -0.1242(2) 0.0482(3) Uani 1 1 d . . . . .
C006 C 0.68245(14) 0.68809(4) -0.2435(2) 0.0494(3) Uani 1 1 d . . . . .
C007 C 0.70218(15) 0.58905(4) 0.3882(2) 0.0526(3) Uani 1 1 d . . . . .
C008 C 0.78805(14) 0.61201(4) 0.2079(2) 0.0540(3) Uani 1 1 d . . . . .
C009 C 0.70616(14) 0.47416(4) 1.0120(2) 0.0559(3) Uani 1 1 d . . . . .
C00A C 0.79372(15) 0.55695(4) 0.5275(2) 0.0569(3) Uani 1 1 d . . . . .
C00B C 0.70337(15) 0.53201(4) 0.6987(2) 0.0570(3) Uani 1 1 d . . . . .
C00C C 0.79412(15) 0.50108(4) 0.8470(3) 0.0571(3) Uani 1 1 d . . . . .
C00D C 0.92868(16) 0.66051(5) -0.1962(2) 0.0596(3) Uani 1 1 d . . . . .
C00E C 0.41073(15) 0.70404(4) -0.1653(3) 0.0612(3) Uani 1 1 d . . . . .
C00F C 0.72175(17) 0.71130(4) -0.4384(2) 0.0606(3) Uani 1 1 d . . . . .
C00G C 0.45333(15) 0.64736(5) 0.2080(3) 0.0621(4) Uani 1 1 d . . . . .
C00H C 0.29889(16) 0.69550(5) -0.0191(3) 0.0679(4) Uani 1 1 d . . . . .
C00I C 0.96486(19) 0.68418(5) -0.3898(3) 0.0682(4) Uani 1 1 d . . . . .
C00J C 0.79981(17) 0.44447(5) 1.1615(3) 0.0664(4) Uani 1 1 d . . . . .
C00K C 0.31991(16) 0.66730(5) 0.1646(3) 0.0692(4) Uani 1 1 d . . . . .
C00L C 0.86340(19) 0.70916(5) -0.5107(3) 0.0688(4) Uani 1 1 d . . . . .
C00M C 0.7152(2) 0.41768(6) 1.3303(3) 0.0753(4) Uani 1 1 d . . . . .
H00K H 0.9965(17) 0.6433(5) -0.114(3) 0.063(4) Uiso 1 1 d . . . . .
H00E H 0.8368(17) 0.5369(5) 0.421(3) 0.070(4) Uiso 1 1 d . . . . .
H00G H 0.6246(19) 0.5152(5) 0.610(3) 0.076(5) Uiso 1 1 d . . . . .
H00I H 0.8646(17) 0.5176(5) 0.937(3) 0.062(4) Uiso 1 1 d . . . . .
H00L H 0.4022(17) 0.7242(5) -0.293(3) 0.070(4) Uiso 1 1 d . . . . .
H00C H 0.6487(18) 0.4931(5) 1.120(3) 0.073(4) Uiso 1 1 d . . . . .
H00A H 0.6193(17) 0.5747(5) 0.310(3) 0.068(4) Uiso 1 1 d . . . . .
H00J H 0.8482(18) 0.4821(5) 0.740(3) 0.072(4) Uiso 1 1 d . . . . .
H00B H 0.6607(16) 0.6100(5) 0.491(3) 0.060(4) Uiso 1 1 d . . . . .
H00D H 0.632(2) 0.4572(6) 0.924(3) 0.082(5) Uiso 1 1 d . . . . .
H00F H 0.8719(18) 0.5725(5) 0.611(3) 0.068(4) Uiso 1 1 d . . . . .
H00H H 0.6481(17) 0.5519(5) 0.804(3) 0.069(4) Uiso 1 1 d . . . . .
H00S H 0.236(2) 0.6608(5) 0.272(3) 0.081(5) Uiso 1 1 d . . . . .
H00N H 0.4593(17) 0.6280(5) 0.338(3) 0.073(4) Uiso 1 1 d . . . . .
H00P H 1.063(2) 0.6825(5) -0.442(3) 0.082(5) Uiso 1 1 d . . . . .
H00T H 0.8924(19) 0.7252(6) -0.644(3) 0.082(5) Uiso 1 1 d . . . . .
H00M H 0.6480(18) 0.7286(5) -0.523(3) 0.071(4) Uiso 1 1 d . . . . .
H00Q H 0.878(2) 0.4626(6) 1.250(3) 0.094(6) Uiso 1 1 d . . . . .
H00U H 0.659(2) 0.4359(6) 1.436(3) 0.095(6) Uiso 1 1 d . . . . .
H00O H 0.205(2) 0.7100(6) -0.039(3) 0.086(5) Uiso 1 1 d . . . . .
H00R H 0.853(2) 0.4257(6) 1.059(3) 0.098(6) Uiso 1 1 d . . . . .
H00V H 0.779(3) 0.3998(8) 1.430(4) 0.121(8) Uiso 1 1 d . . . . .
H00W H 0.642(3) 0.3993(8) 1.253(4) 0.117(7) Uiso 1 1 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
N001 C003 1.4262(16) . ?
N001 C005 1.4202(15) . ?
N001 C008 1.4060(15) . ?
O002 C008 1.2103(16) . ?
C003 C004 1.4024(17) . ?
C003 C00G 1.3878(19) . ?
C004 C006 1.4397(18) . ?
C004 C00E 1.3987(18) . ?
C005 C006 1.4007(17) . ?
C005 C00D 1.3862(19) . ?
C006 C00F 1.3909(18) . ?
C007 C008 1.5006(18) . ?
C007 C00A 1.5210(17) . ?
C007 H00A 0.979(16) . ?
C007 H00B 0.967(15) . ?
C009 C00C 1.5158(18) . ?
C009 C00J 1.5149(18) . ?
C009 H00C 1.014(17) . ?
C009 H00D 0.988(18) . ?
C00A C00B 1.5180(19) . ?
C00A H00E 0.969(17) . ?
C00A H00F 0.980(16) . ?
C00B C00C 1.5212(18) . ?
C00B H00G 1.019(18) . ?
C00B H00H 1.012(16) . ?
C00C H00I 0.965(16) . ?
C00C H00J 0.995(17) . ?
C00D C00I 1.385(2) . ?
C00D H00K 0.938(15) . ?
C00E C00H 1.369(2) . ?
C00E H00L 0.970(16) . ?
C00F C00L 1.374(2) . ?
C00F H00M 0.985(16) . ?
C00G C00K 1.387(2) . ?
C00G H00N 0.960(17) . ?
C00H C00K 1.386(2) . ?
C00H H00O 0.975(19) . ?
C00I C00L 1.386(2) . ?
C00I H00P 0.953(19) . ?
C00J C00M 1.512(2) . ?
C00J H00Q 1.04(2) . ?
C00J H00R 0.97(2) . ?
C00K H00S 1.018(18) . ?
C00L H00T 0.962(18) . ?
C00M H00U 0.99(2) . ?
C00M H00V 0.98(2) . ?
C00M H00W 0.98(2) . ?

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
C005 N001 C003 107.59(9) . . ?
C008 N001 C003 129.82(10) . . ?
C008 N001 C005 122.57(10) . . ?
C004 C003 N001 108.14(11) . . ?
C00G C003 N001 132.01(11) . . ?
C00G C003 C004 119.84(12) . . ?
C003 C004 C006 107.99(10) . . ?
C00E C004 C003 120.51(12) . . ?
C00E C004 C006 131.48(12) . . ?
C006 C005 N001 108.62(11) . . ?
C00D C005 N001 130.74(11) . . ?
C00D C005 C006 120.64(12) . . ?
C005 C006 C004 107.62(10) . . ?
C00F C006 C004 131.95(12) . . ?
C00F C006 C005 120.43(12) . . ?
C008 C007 C00A 112.83(11) . . ?
C008 C007 H00A 108.4(9) . . ?
C008 C007 H00B 108.8(8) . . ?
C00A C007 H00A 110.4(9) . . ?
C00A C007 H00B 110.1(8) . . ?
H00A C007 H00B 106.1(12) . . ?
N001 C008 C007 118.76(11) . . ?
O002 C008 N001 119.34(12) . . ?
O002 C008 C007 121.89(11) . . ?
C00C C009 H00C 110.6(9) . . ?
C00C C009 H00D 110.2(10) . . ?
C00J C009 C00C 113.15(11) . . ?
C00J C009 H00C 107.7(9) . . ?
C00J C009 H00D 109.5(10) . . ?
H00C C009 H00D 105.4(14) . . ?
C007 C00A H00E 108.6(9) . . ?
C007 C00A H00F 108.5(9) . . ?
C00B C00A C007 112.22(11) . . ?
C00B C00A H00E 108.6(9) . . ?
C00B C00A H00F 109.8(9) . . ?
H00E C00A H00F 109.1(13) . . ?
C00A C00B C00C 113.03(11) . . ?
C00A C00B H00G 109.2(9) . . ?
C00A C00B H00H 111.2(9) . . ?
C00C C00B H00G 108.8(9) . . ?
C00C C00B H00H 109.2(9) . . ?
H00G C00B H00H 105.0(13) . . ?
C009 C00C C00B 114.36(11) . . ?
C009 C00C H00I 108.6(9) . . ?
C009 C00C H00J 109.7(9) . . ?
C00B C00C H00I 108.0(9) . . ?
C00B C00C H00J 107.8(9) . . ?
H00I C00C H00J 108.2(13) . . ?
C005 C00D H00K 119.6(9) . . ?
C00I C00D C005 117.65(13) . . ?
C00I C00D H00K 122.8(9) . . ?
C004 C00E H00L 117.6(10) . . ?
C00H C00E C004 119.25(13) . . ?
C00H C00E H00L 123.1(10) . . ?
C006 C00F H00M 119.9(9) . . ?
C00L C00F C006 119.03(13) . . ?
C00L C00F H00M 121.1(9) . . ?
C003 C00G H00N 124.5(10) . . ?
C00K C00G C003 118.51(14) . . ?
C00K C00G H00N 117.0(10) . . ?
C00E C00H C00K 120.15(14) . . ?
C00E C00H H00O 120.6(11) . . ?
C00K C00H H00O 119.2(11) . . ?
C00D C00I C00L 122.20(15) . . ?
C00D C00I H00P 118.0(11) . . ?
C00L C00I H00P 119.8(11) . . ?
C009 C00J H00Q 108.6(11) . . ?
C009 C00J H00R 108.2(12) . . ?
C00M C00J C009 114.31(13) . . ?
C00M C00J H00Q 110.2(11) . . ?
C00M C00J H00R 109.3(12) . . ?
H00Q C00J H00R 105.8(16) . . ?
C00G C00K H00S 118.4(10) . . ?
C00H C00K C00G 121.75(14) . . ?
C00H C00K H00S 119.8(10) . . ?
C00F C00L C00I 120.05(13) . . ?
C00F C00L H00T 119.9(11) . . ?
C00I C00L H00T 120.0(11) . . ?
C00J C00M H00U 111.1(11) . . ?
C00J C00M H00V 112.6(14) . . ?
C00J C00M H00W 112.8(14) . . ?
H00U C00M H00V 105.9(16) . . ?
H00U C00M H00W 105.3(18) . . ?
H00V C00M H00W 108.8(19) . . ?

_olex2_exptl_crystal_mounting_method loop
_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 1.468
_oxdiff_exptl_absorpt_empirical_full_min 0.627
####################################################################### 
# 
# 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_cz-7-20191226
_database_code_depnum_ccdc_archive 'CCDC 2050877'
loop_
_audit_author_name
_audit_author_address
Tulianjing
;Institute of Molecular Aggregation Science, Tianjin University
China
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-07-18 downloaded from the CCDC.
;
_audit_creation_date             2020-12-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 N O'
_chemical_formula_sum            'C19 H21 N O'
_chemical_formula_weight         279.37
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H21ON
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   5.80290(10)
_cell_length_b                   29.1697(4)
_cell_length_c                   9.1710(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1552.36(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5460
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.7700
_cell_measurement_theta_min      6.0550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.567
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66150
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8834
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.045
_diffrn_reflns_theta_max         67.045
_diffrn_reflns_theta_min         5.055
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -94.00 -66.00   1.00    4.15    --  -41.12-136.00  94.00   28
  2  ω   -112.00 -19.00   1.00    4.15    --  -41.12 -57.00 -30.00   93
  3  ω    -68.00  26.00   1.00    4.15    --  -41.12  57.00 120.00   94
  4  ω     57.00  83.00   1.00    4.15    --   41.12-133.00 -87.00   26
  5  ω    -30.00  68.00   1.00    4.15    --   41.12 -57.00-150.00   98
  6  ω     32.00 128.00   1.00   16.61    --  105.32 -77.00   0.00   96
  7  ω     91.00 122.00   1.00   16.61    --  105.32 133.00 -18.00   31
  8  ω     89.00 157.00   1.00   16.61    --  105.32 -15.00-150.00   68
  9  ω    131.00 178.00   1.00   16.61    --  105.32 125.00  30.00   47
 10  ω     32.00 129.00   1.00   16.61    --  105.32 -45.00 120.00   97
 11  ω     45.00 132.00   1.00   16.61    --  105.32 -30.00 -30.00   87
 12  ω    143.00 169.00   1.00   16.61    --  105.32 133.00 -18.00   26
 13  ω     35.00  88.00   1.00   16.61    --  105.32 -77.00 -60.00   53
 14  ω     24.00  76.00   1.00   16.61    --  105.32 -15.00-150.00   52
 15  ω     71.00  96.00   1.00   16.61    --  105.32  15.00 -60.00   25
 16  ω    139.00 171.00   1.00   16.61    --  105.32  15.00 -60.00   32
 17  ω     40.00 115.00   1.00   16.61    --  105.32-125.00-180.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0097462000
_diffrn_orient_matrix_UB_12      -0.1332212000
_diffrn_orient_matrix_UB_13      -0.0321112000
_diffrn_orient_matrix_UB_21      -0.0022283000
_diffrn_orient_matrix_UB_22      -0.1021711000
_diffrn_orient_matrix_UB_23      0.0419219000
_diffrn_orient_matrix_UB_31      -0.2652842000
_diffrn_orient_matrix_UB_32      0.0057708000
_diffrn_orient_matrix_UB_33      0.0008234000
_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         0.846
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                2613
_reflns_number_total             2715
_reflns_odcompleteness_completeness 99.88
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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         0.111
_refine_diff_density_min         -0.106
_refine_diff_density_rms         0.021
_refine_ls_abs_structure_details 
;
 Flack x determined using 1165 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.15(17)
_refine_ls_extinction_coef       0.0024(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2715
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0294
_refine_ls_restrained_S_all      1.027
_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)+(0.0537P)²+0.0503P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0834
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C008(H00A,H00B), C00B(H00D,H00E), C00C(H00F,H00G), C00E(H00I,H00J), C00J(H00O,
 H00P)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00C), C00D(H00H), C00F(H00K), C00G(H00L), C00H(H00M),
 C00I(H00N), C00K(H00Q)
2.c Idealised Me refined as rotating group:
 C00L(H00R,H00S,H00T)
;
_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
N001 N 0.8531(2) 0.63593(5) 0.58028(18) 0.0487(4) Uani 1 1 d . . . . .
O002 O 0.7335(3) 0.59698(7) 0.7793(2) 0.0809(5) Uani 1 1 d . . . . .
C003 C 1.0400(3) 0.65796(5) 0.6521(2) 0.0481(4) Uani 1 1 d . . . . .
C004 C 1.0422(3) 0.68059(6) 0.4127(2) 0.0499(4) Uani 1 1 d . . . . .
C005 C 0.7080(3) 0.60432(6) 0.6508(2) 0.0535(4) Uani 1 1 d . . . . .
C006 C 0.8539(3) 0.65087(6) 0.4325(2) 0.0485(4) Uani 1 1 d . . . . .
C007 C 1.1589(3) 0.68447(6) 0.5501(2) 0.0499(4) Uani 1 1 d . . . . .
C008 C 0.3887(3) 0.54577(6) 0.6517(3) 0.0575(5) Uani 1 1 d . . . . .
H00A H 0.493025 0.524188 0.697632 0.069 Uiso 1 1 calc R . . . .
H00B H 0.306449 0.561908 0.728123 0.069 Uiso 1 1 calc R . . . .
C009 C 1.1104(4) 0.65592(7) 0.7970(3) 0.0598(5) Uani 1 1 d . . . . .
H009 H 1.030848 0.638453 0.865301 0.072 Uiso 1 1 calc R . . . .
C00A C 0.7076(4) 0.64181(8) 0.3156(2) 0.0630(5) Uani 1 1 d . . . . .
H00C H 0.582977 0.622047 0.326263 0.076 Uiso 1 1 calc R . . . .
C00B C 0.0664(4) 0.48653(7) 0.6433(2) 0.0590(5) Uani 1 1 d . . . . .
H00D H 0.164086 0.464643 0.693484 0.071 Uiso 1 1 calc R . . . .
H00E H -0.019072 0.503458 0.716511 0.071 Uiso 1 1 calc R . . . .
C00C C 0.5272(3) 0.58001(6) 0.5626(2) 0.0525(4) Uani 1 1 d . . . . .
H00F H 0.601180 0.564041 0.482521 0.063 Uiso 1 1 calc R . . . .
H00G H 0.423066 0.602545 0.521332 0.063 Uiso 1 1 calc R . . . .
C00D C 1.0817(4) 0.70141(7) 0.2777(3) 0.0612(5) Uani 1 1 d . . . . .
H00H H 1.206233 0.721095 0.265110 0.073 Uiso 1 1 calc R . . . .
C00E C 0.2177(3) 0.51977(7) 0.5583(2) 0.0592(5) Uani 1 1 d . . . . .
H00I H 0.301668 0.502777 0.484475 0.071 Uiso 1 1 calc R . . . .
H00J H 0.119498 0.541659 0.508468 0.071 Uiso 1 1 calc R . . . .
C00F C 1.3041(4) 0.68104(8) 0.8353(3) 0.0687(6) Uani 1 1 d . . . . .
H00K H 1.354112 0.680403 0.931643 0.082 Uiso 1 1 calc R . . . .
C00G C 1.4256(4) 0.70703(8) 0.7351(3) 0.0692(6) Uani 1 1 d . . . . .
H00L H 1.555814 0.723148 0.764554 0.083 Uiso 1 1 calc R . . . .
C00H C 0.9348(4) 0.69249(7) 0.1640(3) 0.0680(5) Uani 1 1 d . . . . .
H00M H 0.958479 0.706392 0.074006 0.082 Uiso 1 1 calc R . . . .
C00I C 1.3548(3) 0.70913(7) 0.5920(3) 0.0621(5) Uani 1 1 d . . . . .
H00N H 1.435632 0.726621 0.524436 0.074 Uiso 1 1 calc R . . . .
C00J C -0.1015(4) 0.46078(8) 0.5477(3) 0.0672(6) Uani 1 1 d . . . . .
H00O H -0.015703 0.443736 0.474880 0.081 Uiso 1 1 calc R . . . .
H00P H -0.198088 0.482724 0.496894 0.081 Uiso 1 1 calc R . . . .
C00K C 0.7517(4) 0.66287(8) 0.1833(3) 0.0705(6) Uani 1 1 d . . . . .
H00Q H 0.654790 0.656875 0.104789 0.085 Uiso 1 1 calc R . . . .
C00L C -0.2545(4) 0.42778(8) 0.6314(3) 0.0774(7) Uani 1 1 d . . . . .
H00R H -0.362610 0.413847 0.565700 0.116 Uiso 1 1 calc GR . . . .
H00S H -0.336532 0.444191 0.705817 0.116 Uiso 1 1 calc GR . . . .
H00T H -0.161161 0.404431 0.675588 0.116 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
N001 C003 1.422(2) . ?
N001 C005 1.406(2) . ?
N001 C006 1.424(3) . ?
O002 C005 1.207(3) . ?
C003 C007 1.396(3) . ?
C003 C009 1.392(3) . ?
C004 C006 1.407(2) . ?
C004 C007 1.434(3) . ?
C004 C00D 1.398(3) . ?
C005 C00C 1.503(3) . ?
C006 C00A 1.392(3) . ?
C007 C00I 1.399(3) . ?
C008 H00A 0.9700 . ?
C008 H00B 0.9700 . ?
C008 C00C 1.520(3) . ?
C008 C00E 1.514(3) . ?
C009 H009 0.9300 . ?
C009 C00F 1.387(3) . ?
C00A H00C 0.9300 . ?
C00A C00K 1.384(3) . ?
C00B H00D 0.9700 . ?
C00B H00E 0.9700 . ?
C00B C00E 1.523(3) . ?
C00B C00J 1.511(3) . ?
C00C H00F 0.9700 . ?
C00C H00G 0.9700 . ?
C00D H00H 0.9300 . ?
C00D C00H 1.372(3) . ?
C00E H00I 0.9700 . ?
C00E H00J 0.9700 . ?
C00F H00K 0.9300 . ?
C00F C00G 1.385(4) . ?
C00G H00L 0.9300 . ?
C00G C00I 1.376(4) . ?
C00H H00M 0.9300 . ?
C00H C00K 1.381(3) . ?
C00I H00N 0.9300 . ?
C00J H00O 0.9700 . ?
C00J H00P 0.9700 . ?
C00J C00L 1.518(3) . ?
C00K H00Q 0.9300 . ?
C00L H00R 0.9600 . ?
C00L H00S 0.9600 . ?
C00L H00T 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C003 N001 C006 107.47(15) . . ?
C005 N001 C003 122.68(17) . . ?
C005 N001 C006 129.82(17) . . ?
C007 C003 N001 108.47(17) . . ?
C009 C003 N001 130.27(18) . . ?
C009 C003 C007 121.25(17) . . ?
C006 C004 C007 107.59(16) . . ?
C00D C004 C006 120.60(19) . . ?
C00D C004 C007 131.78(17) . . ?
N001 C005 C00C 118.68(18) . . ?
O002 C005 N001 119.50(18) . . ?
O002 C005 C00C 121.82(18) . . ?
C004 C006 N001 108.26(17) . . ?
C00A C006 N001 132.29(18) . . ?
C00A C006 C004 119.45(18) . . ?
C003 C007 C004 108.17(15) . . ?
C003 C007 C00I 120.13(19) . . ?
C00I C007 C004 131.70(19) . . ?
H00A C008 H00B 107.9 . . ?
C00C C008 H00A 109.3 . . ?
C00C C008 H00B 109.3 . . ?
C00E C008 H00A 109.3 . . ?
C00E C008 H00B 109.3 . . ?
C00E C008 C00C 111.82(18) . . ?
C003 C009 H009 121.4 . . ?
C00F C009 C003 117.2(2) . . ?
C00F C009 H009 121.4 . . ?
C006 C00A H00C 120.7 . . ?
C00K C00A C006 118.6(2) . . ?
C00K C00A H00C 120.7 . . ?
H00D C00B H00E 107.8 . . ?
C00E C00B H00D 109.0 . . ?
C00E C00B H00E 109.0 . . ?
C00J C00B H00D 109.0 . . ?
C00J C00B H00E 109.0 . . ?
C00J C00B C00E 113.03(18) . . ?
C005 C00C C008 112.97(17) . . ?
C005 C00C H00F 109.0 . . ?
C005 C00C H00G 109.0 . . ?
C008 C00C H00F 109.0 . . ?
C008 C00C H00G 109.0 . . ?
H00F C00C H00G 107.8 . . ?
C004 C00D H00H 120.4 . . ?
C00H C00D C004 119.26(18) . . ?
C00H C00D H00H 120.4 . . ?
C008 C00E C00B 114.01(18) . . ?
C008 C00E H00I 108.7 . . ?
C008 C00E H00J 108.7 . . ?
C00B C00E H00I 108.7 . . ?
C00B C00E H00J 108.7 . . ?
H00I C00E H00J 107.6 . . ?
C009 C00F H00K 118.9 . . ?
C00G C00F C009 122.3(2) . . ?
C00G C00F H00K 118.9 . . ?
C00F C00G H00L 119.8 . . ?
C00I C00G C00F 120.3(2) . . ?
C00I C00G H00L 119.8 . . ?
C00D C00H H00M 120.0 . . ?
C00D C00H C00K 120.0(2) . . ?
C00K C00H H00M 120.0 . . ?
C007 C00I H00N 120.6 . . ?
C00G C00I C007 118.8(2) . . ?
C00G C00I H00N 120.6 . . ?
C00B C00J H00O 108.9 . . ?
C00B C00J H00P 108.9 . . ?
C00B C00J C00L 113.5(2) . . ?
H00O C00J H00P 107.7 . . ?
C00L C00J H00O 108.9 . . ?
C00L C00J H00P 108.9 . . ?
C00A C00K H00Q 118.9 . . ?
C00H C00K C00A 122.1(2) . . ?
C00H C00K H00Q 118.9 . . ?
C00J C00L H00R 109.5 . . ?
C00J C00L H00S 109.5 . . ?
C00J C00L H00T 109.5 . . ?
H00R C00L H00S 109.5 . . ?
H00R C00L H00T 109.5 . . ?
H00S C00L H00T 109.5 . . ?

_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 1.451
_oxdiff_exptl_absorpt_empirical_full_min 0.535
####################################################################### 
# 
# 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_cpo-film
_database_code_depnum_ccdc_archive 'CCDC 2050873'
loop_
_audit_author_name
_audit_author_address
Tulianjing
;Institute of Molecular Aggregation Science, Tianjin University
China
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-07-18 downloaded from the CCDC.
;
_audit_creation_date             2020-12-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H13 N O'
_chemical_formula_sum            'C15 H13 N O'
_chemical_formula_weight         223.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H13 O1 N1'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.9435(2)
_cell_length_b                   15.3282(3)
_cell_length_c                   16.5685(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2271.34(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3968
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.0860
_cell_measurement_theta_min      5.7990
_shelx_estimated_absorpt_T_max   0.860
_shelx_estimated_absorpt_T_min   0.835
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82159
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_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    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7094
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.072
_diffrn_reflns_theta_max         67.072
_diffrn_reflns_theta_min         5.340
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -33.00   1.00    4.37    --  -40.87 -37.00  90.00   81
  2  ω     51.00  90.00   1.00    4.37    --   40.87-125.00 -30.00   39
  3  ω    -16.00  61.00   1.00    4.37    --   40.87 -57.00 -90.00   77
  4  ω     54.00  89.00   1.00   17.47    --  105.32 -94.00 -90.00   35
  5  ω     41.00 131.00   1.00   17.47    --  105.32 -45.00 -60.00   90
  6  ω     24.00  63.00   1.00   17.47    --  105.32 -94.00-180.00   39
  7  ω     67.00 109.00   1.00   17.47    --  105.32 -94.00-180.00   42
  8  ω     64.00 100.00   1.00   17.47    --  105.32 -94.00  30.00   36
  9  ω     35.00 129.00   1.00   17.47    --  105.32 -45.00-150.00   94
 10  ω     51.00 111.00   1.00   17.47    --  105.32   0.00 -60.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0418953000
_diffrn_orient_matrix_UB_12      -0.0269886000
_diffrn_orient_matrix_UB_13      -0.0866476000
_diffrn_orient_matrix_UB_21      -0.0085150000
_diffrn_orient_matrix_UB_22      -0.0968074000
_diffrn_orient_matrix_UB_23      0.0245950000
_diffrn_orient_matrix_UB_31      -0.1668704000
_diffrn_orient_matrix_UB_32      -0.0018461000
_diffrn_orient_matrix_UB_33      -0.0230333000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1803
_reflns_number_total             2023
_reflns_odcompleteness_completeness 99.91
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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         0.146
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.00138(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2023
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.041
_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)+(0.0563P)²+0.3008P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.0995
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H008(0.059) H009(0.062) H00A(0.06) H00B(0.064) H00C(0.066)
 H00D(0.064) H00E(0.064) H00F(0.068) H00G(0.068) H00H(0.071) H00I(0.119)
 H00J(0.119) H00K(0.119)
 Fixed X: H008(0.620569) H009(0.466548) H00A(0.241171) H00B(0.281346)
 H00C(0.694957) H00D(0.524718) H00E(0.658973) H00F(0.621741) H00G(0.108385)
 H00H(0.129627) H00I(0.505533) H00J(0.666841) H00K(0.638632)
 Fixed Y: H008(0.535786) H009(0.678737) H00A(0.810056) H00B(0.811251)
 H00C(0.487574) H00D(0.544398) H00E(0.607759) H00F(0.558453) H00G(0.908589)
 H00H(0.911349) H00I(0.598323) H00J(0.561517) H00K(0.662435)
 Fixed Z: H008(0.74077) H009(0.975531) H00A(0.651016) H00B(0.932585)
 H00C(0.867073) H00D(0.618462) H00E(0.63506) H00F(0.982683) H00G(0.728663)
 H00H(0.866783) H00I(0.486129) H00J(0.500668) H00K(0.502646)
;
_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
O001 O 0.39295(12) 0.71647(7) 0.58435(5) 0.0653(3) Uani 1 1 d . . . . .
N002 N 0.43361(10) 0.68260(6) 0.71522(5) 0.0415(3) Uani 1 1 d . . . . .
C003 C 0.49843(12) 0.63796(7) 0.78227(6) 0.0400(3) Uani 1 1 d . . . . .
C004 C 0.45077(13) 0.67986(7) 0.85332(7) 0.0419(3) Uani 1 1 d . . . . .
C005 C 0.34206(12) 0.75062(7) 0.74638(7) 0.0410(3) Uani 1 1 d . . . . .
C006 C 0.35286(12) 0.75056(7) 0.83053(7) 0.0426(3) Uani 1 1 d . . . . .
C007 C 0.45812(14) 0.67073(8) 0.63268(7) 0.0460(3) Uani 1 1 d . . . . .
C008 C 0.58974(14) 0.56488(8) 0.78713(7) 0.0492(3) Uani 1 1 d . . . . .
H008 H 0.620569 0.535786 0.740770 0.059 Uiso 1 1 calc R . . . .
C009 C 0.49720(14) 0.65042(9) 0.92873(7) 0.0514(3) Uani 1 1 d . . . . .
H009 H 0.466548 0.678737 0.975531 0.062 Uiso 1 1 calc R . . . .
C00A C 0.24974(14) 0.80995(8) 0.70696(7) 0.0501(3) Uani 1 1 d . . . . .
H00A H 0.241171 0.810056 0.651016 0.060 Uiso 1 1 calc R . . . .
C00B C 0.27351(15) 0.81091(9) 0.87661(8) 0.0536(3) Uani 1 1 d . . . . .
H00B H 0.281346 0.811251 0.932585 0.064 Uiso 1 1 calc R . . . .
C00C C 0.63377(15) 0.53643(8) 0.86300(8) 0.0546(3) Uani 1 1 d . . . . .
H00C H 0.694957 0.487574 0.867073 0.066 Uiso 1 1 calc R . . . .
C00D C 0.56579(15) 0.60132(9) 0.60570(7) 0.0536(3) Uani 1 1 d . . . . .
H00D H 0.524718 0.544398 0.618462 0.064 Uiso 1 1 calc R . . . .
H00E H 0.658973 0.607759 0.635060 0.064 Uiso 1 1 calc R . . . .
C00E C 0.58924(15) 0.57869(9) 0.93276(8) 0.0563(3) Uani 1 1 d . . . . .
H00F H 0.621741 0.558453 0.982683 0.068 Uiso 1 1 calc R . . . .
C00F C 0.17125(15) 0.86869(9) 0.75390(9) 0.0568(3) Uani 1 1 d . . . . .
H00G H 0.108385 0.908589 0.728663 0.068 Uiso 1 1 calc R . . . .
C00G C 0.18296(16) 0.87022(9) 0.83722(9) 0.0596(4) Uani 1 1 d . . . . .
H00H H 0.129627 0.911349 0.866783 0.071 Uiso 1 1 calc R . . . .
C00H C 0.5971(2) 0.60636(12) 0.51544(9) 0.0796(5) Uani 1 1 d . . . . .
H00I H 0.505533 0.598323 0.486129 0.119 Uiso 1 1 calc GR . . . .
H00J H 0.666841 0.561517 0.500668 0.119 Uiso 1 1 calc GR . . . .
H00K H 0.638632 0.662435 0.502646 0.119 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
O001 C007 1.2136(15) . ?
N002 C003 1.4277(14) . ?
N002 C005 1.4227(15) . ?
N002 C007 1.3969(14) . ?
C003 C004 1.4071(15) . ?
C003 C008 1.3885(18) . ?
C004 C006 1.4437(17) . ?
C004 C009 1.3917(16) . ?
C005 C006 1.3976(16) . ?
C005 C00A 1.3912(17) . ?
C006 C00B 1.3936(17) . ?
C007 C00D 1.5030(18) . ?
C008 H008 0.9300 . ?
C008 C00C 1.3876(17) . ?
C009 H009 0.9300 . ?
C009 C00E 1.3751(19) . ?
C00A H00A 0.9300 . ?
C00A C00F 1.3814(19) . ?
C00B H00B 0.9300 . ?
C00B C00G 1.381(2) . ?
C00C H00C 0.9300 . ?
C00C C00E 1.3835(19) . ?
C00D H00D 0.9700 . ?
C00D H00E 0.9700 . ?
C00D C00H 1.5234(18) . ?
C00E H00F 0.9300 . ?
C00F H00G 0.9300 . ?
C00F C00G 1.385(2) . ?
C00G H00H 0.9300 . ?
C00H H00I 0.9600 . ?
C00H H00J 0.9600 . ?
C00H H00K 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C005 N002 C003 107.61(9) . . ?
C007 N002 C003 129.46(10) . . ?
C007 N002 C005 122.75(10) . . ?
C004 C003 N002 108.01(10) . . ?
C008 C003 N002 132.11(10) . . ?
C008 C003 C004 119.86(10) . . ?
C003 C004 C006 107.91(10) . . ?
C009 C004 C003 120.84(11) . . ?
C009 C004 C006 131.24(11) . . ?
C006 C005 N002 108.77(9) . . ?
C00A C005 N002 130.56(11) . . ?
C00A C005 C006 120.65(11) . . ?
C005 C006 C004 107.66(9) . . ?
C00B C006 C004 131.59(11) . . ?
C00B C006 C005 120.73(11) . . ?
O001 C007 N002 119.70(12) . . ?
O001 C007 C00D 121.36(11) . . ?
N002 C007 C00D 118.95(11) . . ?
C003 C008 H008 120.9 . . ?
C00C C008 C003 118.22(11) . . ?
C00C C008 H008 120.9 . . ?
C004 C009 H009 120.6 . . ?
C00E C009 C004 118.78(11) . . ?
C00E C009 H009 120.6 . . ?
C005 C00A H00A 121.2 . . ?
C00F C00A C005 117.60(12) . . ?
C00F C00A H00A 121.2 . . ?
C006 C00B H00B 120.8 . . ?
C00G C00B C006 118.45(12) . . ?
C00G C00B H00B 120.8 . . ?
C008 C00C H00C 119.1 . . ?
C00E C00C C008 121.87(12) . . ?
C00E C00C H00C 119.1 . . ?
C007 C00D H00D 109.2 . . ?
C007 C00D H00E 109.2 . . ?
C007 C00D C00H 111.95(12) . . ?
H00D C00D H00E 107.9 . . ?
C00H C00D H00D 109.2 . . ?
C00H C00D H00E 109.2 . . ?
C009 C00E C00C 120.40(12) . . ?
C009 C00E H00F 119.8 . . ?
C00C C00E H00F 119.8 . . ?
C00A C00F H00G 118.9 . . ?
C00A C00F C00G 122.27(12) . . ?
C00G C00F H00G 118.9 . . ?
C00B C00G C00F 120.28(12) . . ?
C00B C00G H00H 119.9 . . ?
C00F C00G H00H 119.9 . . ?
C00D C00H H00I 109.5 . . ?
C00D C00H H00J 109.5 . . ?
C00D C00H H00K 109.5 . . ?
H00I C00H H00J 109.5 . . ?
H00I C00H H00K 109.5 . . ?
H00J C00H H00K 109.5 . . ?

_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 1.208
_oxdiff_exptl_absorpt_empirical_full_min 0.675
####################################################################### 
# 
# 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_Cz-5
_database_code_depnum_ccdc_archive 'CCDC 2050875'
loop_
_audit_author_name
_audit_author_address
Tulianjing
;Institute of Molecular Aggregation Science, Tianjin University
China
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-07-18 downloaded from the CCDC.
;
_audit_creation_date             2019-12-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H17 N O'
_chemical_formula_sum            'C17 H17 N O'
_chemical_formula_weight         251.33
_chemical_absolute_configuration unk
_chemical_oxdiff_formula         C17H17ON
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           ' P 2c -2n'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,z+1/2
3 -x+1/2,y+1/2,z+1/2
4 x+1/2,-y+1/2,z

_symmetry_Int_Tables_number      33
_cell_length_a                   5.97062(8)
_cell_length_b                   24.9105(4)
_cell_length_c                   9.11019(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1354.97(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11563
_cell_measurement_temperature    300
_cell_measurement_theta_max      73.0290
_cell_measurement_theta_min      7.0740
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.2319
_exptl_crystal_description       cube
_exptl_crystal_F_000             537.5648
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_min          ?
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            18996
_diffrn_reflns_theta_full        67.0733
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         3.55
_diffrn_ambient_temperature      300
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9764
_diffrn_measured_fraction_theta_max 0.9764
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -113.00 -14.00   1.00    1.00    --  -41.12 -57.00-150.00   99
  2  ω    -65.00  33.00   1.00    1.00    --  -41.12  37.00 -30.00   98
  3  ω    -39.00 -13.00   1.00    1.00    --  -41.12 -57.00  60.00   26
  4  ω    -60.00  32.00   1.00    1.00    --  -41.12  37.00-120.00   92
  5  ω    -85.00 -18.00   1.00    1.00    --  -41.12 -37.00 120.00   67
  6  ω     23.00  97.00   1.00    1.00    --   41.12-125.00  90.00   74
  7  ω      6.00  31.00   1.00    1.00    --   42.00  88.00-167.13   25
  8  ω     11.00  36.00   1.00    1.00    --   46.00  84.00 -52.43   25
  9  ω     11.00  36.00   1.00    1.00    --   46.00  84.00 132.64   25
 10  ω     11.00  36.00   1.00    1.00    --   46.00  84.00  58.55   25
 11  ω     16.00  41.00   1.00    1.00    --   50.00  82.00-137.60   25
 12  ω     17.00  45.00   1.00    1.00    --   50.00  82.00  85.61   28
 13  ω     16.00  41.00   1.00    1.00    --   50.00  81.00  14.38   25
 14  ω     86.00 128.00   1.00    1.00    --   58.00  77.00 -68.09   42
 15  ω     25.00  52.00   1.00    1.00    --   58.00  77.00   6.22   27
 16  ω     31.00  73.00   1.00    1.00    --   58.00  77.00-129.13   42
 17  ω     90.00 133.00   1.00    1.00    --   58.00  77.00-129.13   43
 18  ω     26.00  55.00   1.00    1.00    --   58.00  77.00 -68.09   29
 19  ω     31.00  71.00   1.00    1.00    --   62.00  74.00 -35.92   40
 20  ω     33.00  59.00   1.00    1.00    --   66.00  77.00 131.56   26
 21  ω     34.00  61.00   1.00    1.00    --   66.00  75.00  86.03   27
 22  ω     34.00  66.00   1.00    1.00    --   66.00  76.00 157.96   32
 23  ω     39.00  79.00   1.00    1.00    --   70.00  77.00-173.37   40
 24  ω     99.00 126.00   1.00    1.00    --   70.00  77.00-173.37   27
 25  ω     39.00  67.00   1.00    1.00    --   70.00  76.00  56.82   28
 26  ω     46.00  72.00   1.00    3.39    --   78.00  75.00  13.87   26
 27  ω     76.00 102.00   1.00    3.39    --  105.32  61.00-150.00   26
 28  ω     32.00 109.00   1.00    3.39    --  105.32 -94.00-180.00   77
 29  ω     77.00 103.00   1.00    3.39    --  105.32  61.00  60.00   26
 30  ω     74.00 176.00   1.00    3.39    --  105.32  77.00 120.00  102
 31  ω     76.00 113.00   1.00    3.39    --  105.32  61.00 -30.00   37
 32  ω    127.00 160.00   1.00    3.39    --  105.32  61.00 -60.00   33
 33  ω     74.00 177.00   1.00    3.39    --  105.32  77.00 -90.00  103
 34  ω     23.00 107.00   1.00    3.39    --  105.32 -94.00 -60.00   84
 35  ω     76.00 177.00   1.00    3.39    --  105.32  77.00 -30.00  101
 36  ω     69.00 137.00   1.00    3.39    --  105.32 -77.00 -60.00   68
 37  ω     54.00 105.00   1.00    3.39    --  105.32-125.00 150.00   51
 38  ω    124.00 170.00   1.00    3.39    --  105.32  77.00 150.00   46
 39  ω     73.00  99.00   1.00    3.39    --  105.32  77.00 150.00   26
 40  ω    122.00 148.00   1.00    3.39    --  105.32  77.00   0.00   26
 41  ω     74.00  99.00   1.00    3.39    --  105.32  77.00   0.00   25
 42  ω    122.00 178.00   1.00    3.39    --  105.32  61.00-180.00   56
 43  ω    121.00 162.00   1.00    3.39    --  105.32 125.00   0.00   41
 44  ω     73.00 163.00   1.00    3.39    --  105.32  77.00-120.00   90
 45  ω     74.00 143.00   1.00    3.39    --  105.32  77.00  60.00   69
 46  ω     76.00 103.00   1.00    3.39    --  105.32  61.00 -60.00   27
 47  ω     73.00 174.00   1.00    3.39    --  105.32  77.00  90.00  101
 48  ω     77.00 120.00   1.00    3.39    --  105.32  61.00-180.00   43
 49  ω     78.00 109.00   1.00    3.39    --  105.32  77.00-150.00   31
 50  ω    146.00 172.00   1.00    3.39    --  105.32  77.00-150.00   26
 51  ω     79.00 140.00   1.00    3.39    --  105.32  61.00-120.00   61
 52  ω     85.00 156.00   1.00    3.39    --  105.32  61.00  30.00   71
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1111315000
_diffrn_orient_matrix_UB_12      -0.0558084000
_diffrn_orient_matrix_UB_13      0.0008373000
_diffrn_orient_matrix_UB_21      -0.2307663000
_diffrn_orient_matrix_UB_22      0.0263477000
_diffrn_orient_matrix_UB_23      -0.0231721000
_diffrn_orient_matrix_UB_31      0.0312770000
_diffrn_orient_matrix_UB_32      -0.0039377000
_diffrn_orient_matrix_UB_33      -0.1675080000
_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         0.949
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              29
_reflns_limit_k_min              -29
_reflns_limit_l_max              9
_reflns_limit_l_min              -10
_reflns_number_gt                2290
_reflns_number_total             2356
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.0754
_refine_diff_density_min         -0.1406
_refine_diff_density_rms         0.0306
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_d_res_high            0.8370
_refine_ls_d_res_low             12.4552
_refine_ls_goodness_of_fit_ref   1.1149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    29
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2356
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.1149
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0571P)²+0.0359P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0872
_olex2_refinement_description    
;
;
_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_refinement_flags_posn
N1 N 0.30927(18) 0.38068(4) 0.21574(14) 0.0507(3) Uani 1.000000 .
C1aa C 0.1252(2) 0.35612(5) 0.14270(17) 0.0492(3) Uani 1.000000 .
O0aa O 0.4255(2) 0.42800(6) 0.01770(14) 0.0800(4) Uani 1.000000 .
C2aa C 0.0060(2) 0.32522(5) 0.24470(17) 0.0519(3) Uani 1.000000 .
C3aa C 0.3073(2) 0.36277(5) 0.36435(16) 0.0499(3) Uani 1.000000 .
C4aa C 0.4498(3) 0.37194(6) 0.48186(19) 0.0651(4) Uani 1.000000 .
C10 C 0.9544(3) 0.50777(6) 0.24752(19) 0.0661(4) Uani 1.000000 .
C5aa C 0.6279(2) 0.44492(5) 0.23690(17) 0.0553(3) Uani 1.000000 .
C6aa C 0.1206(2) 0.32888(5) 0.38336(17) 0.0516(3) Uani 1.000000 .
C7aa C 0.4506(2) 0.41810(5) 0.14668(19) 0.0550(3) Uani 1.000000 .
C8aa C 0.4049(3) 0.34724(7) 0.61468(19) 0.0714(4) Uani 1.000000 .
C9aa C -0.1858(2) 0.29758(6) 0.2020(2) 0.0651(4) Uani 1.000000 .
C0ba C -0.1349(3) 0.33072(7) -0.0416(2) 0.0710(4) Uani 1.000000 .
C1ba C 0.0570(3) 0.35898(6) -0.00304(19) 0.0618(4) Uani 1.000000 .
C2ba C 0.0799(3) 0.30446(6) 0.51823(18) 0.0639(4) Uani 1.000000 .
C3ba C 0.7705(2) 0.48455(5) 0.15136(18) 0.0605(3) Uani 1.000000 .
C4ba C 1.1075(3) 0.54641(7) 0.1671(2) 0.0788(5) Uani 1.000000 .
C5ba C -0.2552(3) 0.30053(7) 0.0582(2) 0.0722(5) Uani 1.000000 .
C6ba C 0.2229(3) 0.31372(6) 0.6334(2) 0.0698(4) Uani 1.000000 .
H1ba H 0.1364(3) 0.37896(6) -0.07180(19) 0.0742(4) Uiso 1.000000 R
H0ba H -0.1842(3) 0.33219(7) -0.1383(2) 0.0852(5) Uiso 1.000000 R
H5ba H -0.3830(3) 0.28221(7) 0.0282(2) 0.0867(5) Uiso 1.000000 R
H9aa H -0.2661(2) 0.27738(6) 0.2699(2) 0.0781(5) Uiso 1.000000 R
H2ba H -0.0433(3) 0.28204(6) 0.53017(18) 0.0767(5) Uiso 1.000000 R
H6ba H 0.1973(3) 0.29748(6) 0.7238(2) 0.0837(5) Uiso 1.000000 R
H8aa H 0.5002(3) 0.35339(7) 0.69369(19) 0.0857(5) Uiso 1.000000 R
H4aa H 0.5735(3) 0.39432(6) 0.47158(19) 0.0781(5) Uiso 1.000000 R
H10a H 0.8862(3) 0.52635(6) 0.32972(19) 0.0793(5) Uiso 1.000000 R
H10b H 1.0436(3) 0.47856(6) 0.28673(19) 0.0793(5) Uiso 1.000000 R
H5aa H 0.5567(2) 0.46368(5) 0.31769(17) 0.0663(4) Uiso 1.000000 R
H5ab H 0.7247(2) 0.41759(5) 0.27841(17) 0.0663(4) Uiso 1.000000 R
H3ba H 0.6767(2) 0.51339(5) 0.11487(18) 0.0726(4) Uiso 1.000000 R
H3bb H 0.8372(2) 0.46656(5) 0.06763(18) 0.0726(4) Uiso 1.000000 R
H4ba H 1.182(2) 0.52789(18) 0.0885(12) 0.1182(8) Uiso 1.000000 GR
H4bb H 1.0206(5) 0.5755(4) 0.1278(15) 0.1182(8) Uiso 1.000000 GR
H4bc H 1.2172(17) 0.5603(5) 0.2341(5) 0.1182(8) 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
N1 C1aa 1.4230(17) . ?
N1 C3aa 1.4255(19) . ?
N1 C7aa 1.4060(17) . ?
C1aa C2aa 1.401(2) . ?
C1aa C1ba 1.391(2) . ?
O0aa C7aa 1.210(2) . ?
C2aa C6aa 1.440(2) . ?
C2aa C9aa 1.3915(19) . ?
C3aa C4aa 1.386(2) . ?
C3aa C6aa 1.4088(18) . ?
C4aa C8aa 1.384(3) . ?
C10 C3ba 1.519(2) . ?
C10 C4ba 1.516(2) . ?
C5aa C7aa 1.497(2) . ?
C5aa C3ba 1.5191(18) . ?
C6aa C2ba 1.392(2) . ?
C8aa C6ba 1.381(3) . ?
C9aa C5ba 1.377(3) . ?
C0ba C1ba 1.390(2) . ?
C0ba C5ba 1.381(3) . ?
C2ba C6ba 1.372(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
C3aa N1 C1aa 107.64(11) . . ?
C7aa N1 C1aa 122.64(13) . . ?
C7aa N1 C3aa 129.60(12) . . ?
C2aa C1aa N1 108.57(13) . . ?
C1ba C1aa N1 130.59(13) . . ?
C1ba C1aa C2aa 120.85(12) . . ?
C6aa C2aa C1aa 107.80(11) . . ?
C9aa C2aa C1aa 120.31(15) . . ?
C9aa C2aa C6aa 131.89(14) . . ?
C4aa C3aa N1 132.58(12) . . ?
C6aa C3aa N1 108.11(12) . . ?
C6aa C3aa C4aa 119.29(13) . . ?
C8aa C4aa C3aa 118.89(14) . . ?
C4ba C10 C3ba 113.49(16) . . ?
C3ba C5aa C7aa 113.87(13) . . ?
C3aa C6aa C2aa 107.83(12) . . ?
C2ba C6aa C2aa 131.57(13) . . ?
C2ba C6aa C3aa 120.57(14) . . ?
O0aa C7aa N1 119.68(13) . . ?
C5aa C7aa N1 118.32(14) . . ?
C5aa C7aa O0aa 121.99(13) . . ?
C6ba C8aa C4aa 121.95(17) . . ?
C5ba C9aa C2aa 119.17(16) . . ?
C5ba C0ba C1ba 122.59(17) . . ?
C0ba C1ba C1aa 117.17(15) . . ?
C6ba C2ba C6aa 119.50(14) . . ?
C5aa C3ba C10 110.91(14) . . ?
C0ba C5ba C9aa 119.91(15) . . ?
C2ba C6ba C8aa 119.80(16) . . ?

_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 1.894
_oxdiff_exptl_absorpt_empirical_full_min 0.541
####################################################################### 
# 
# 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_Cz-4
_database_code_depnum_ccdc_archive 'CCDC 2050874'
loop_
_audit_author_name
_audit_author_address
Tulianjing
;Institute of Molecular Aggregation Science, Tianjin University
China
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-07-18 downloaded from the CCDC.
;
_audit_creation_date             2019-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C16 H15 N O'
_chemical_formula_sum            'C16 H15 N O'
_chemical_formula_weight         237.30
_chemical_oxdiff_formula         C16H15ON
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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
5 -x,-y,-z
6 -x-1/2,y-1/2,z
7 x,-y-1/2,z-1/2
8 x-1/2,y,-z-1/2

_symmetry_Int_Tables_number      61
_cell_length_a                   8.83939(11)
_cell_length_b                   15.1885(2)
_cell_length_c                   18.7093(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2511.85(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9405
_cell_measurement_temperature    300
_cell_measurement_theta_max      72.8570
_cell_measurement_theta_min      5.5220
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.2549
_exptl_crystal_description       needle
_exptl_crystal_F_000             1010.9830
_exptl_crystal_preparation       'Solvent evaporation'
_exptl_crystal_recrystallization_method ?
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15782
_diffrn_reflns_theta_full        67.0598
_diffrn_reflns_theta_max         67.06
_diffrn_reflns_theta_min         4.73
_diffrn_ambient_temperature      300
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -90.00  -9.00   1.00    5.24    --  -41.12 126.00  77.00   81
  2  ω   -109.00 -17.00   1.00    5.24    --  -41.12 -37.00-180.00   92
  3  ω    -65.00  32.00   1.00    5.24    --  -41.12  37.00   0.00   97
  4  ω     56.00  81.00   1.00    5.24    --   41.12-126.00   0.00   25
  5  ω     -3.00  60.00   1.00    5.24    --   41.12 -37.00   0.00   63
  6  ω     60.00 107.00   1.00   20.96    --  105.32 -94.00-120.00   47
  7  ω     89.00 163.00   1.00   20.96    --  105.32  61.00-180.00   74
  8  ω     88.00 114.00   1.00   20.96    --  105.32-125.00-150.00   26
  9  ω     62.00 107.00   1.00   20.96    --  105.32 -94.00 -30.00   45
 10  ω     79.00 175.00   1.00   20.96    --  105.32  45.00 -90.00   96
 11  ω     34.00  94.00   1.00   20.96    --  105.32 -61.00   0.00   60
 12  ω    112.00 138.00   1.00   20.96    --  105.32 126.00  77.00   26
 13  ω     39.00 115.00   1.00   20.96    --  105.32-125.00 150.00   76
 14  ω     33.00 120.00   1.00   20.96    --  105.32 -61.00 120.00   87
 15  ω    108.00 178.00   1.00   20.96    --  105.32  30.00 150.00   70
 16  ω     32.00 130.00   1.00   20.96    --  105.32 -45.00-120.00   98
 17  ω     97.00 177.00   1.00   20.96    --  105.32  61.00-150.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0272239000
_diffrn_orient_matrix_UB_12      0.0623794000
_diffrn_orient_matrix_UB_13      0.0636493000
_diffrn_orient_matrix_UB_21      -0.0155716000
_diffrn_orient_matrix_UB_22      -0.0781616000
_diffrn_orient_matrix_UB_23      0.0519901000
_diffrn_orient_matrix_UB_31      0.1714152000
_diffrn_orient_matrix_UB_32      -0.0169014000
_diffrn_orient_matrix_UB_33      -0.0053922000
_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              10
_reflns_limit_h_min              0
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                2061
_reflns_number_total             2244
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.1792
_refine_diff_density_min         -0.3525
_refine_diff_density_rms         0.0773
_refine_ls_d_res_high            0.8371
_refine_ls_d_res_low             9.3546
_refine_ls_goodness_of_fit_ref   1.0554
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0510
_refine_ls_restrained_S_all      1.0554
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0850P)²+0.2688P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1308
_olex2_refinement_description    
;
;
_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_refinement_flags_posn
N1 N 0.29419(11) 0.24394(7) 0.68914(5) 0.0483(3) Uani 1.000000 .
C2 C 0.25530(13) 0.20938(7) 0.75752(6) 0.0461(3) Uani 1.000000 .
C3 C 0.33053(14) 0.25926(8) 0.80978(6) 0.0505(3) Uani 1.000000 .
C4 C 0.25186(16) 0.21524(10) 0.62120(6) 0.0590(4) Uani 1.000000 .
C5 C 0.15800(15) 0.14217(8) 0.77770(7) 0.0549(3) Uani 1.000000 .
C6 C 0.41776(13) 0.32604(8) 0.77365(7) 0.0517(3) Uani 1.000000 .
O1 O 0.2805(2) 0.25962(9) 0.56964(6) 0.1013(5) Uani 1.000000 .
C8 C 0.39289(14) 0.31676(8) 0.70028(7) 0.0506(3) Uani 1.000000 .
C9 C 0.16966(17) 0.12902(10) 0.61430(7) 0.0610(4) Uani 1.000000 .
C10 C 0.31017(18) 0.24060(10) 0.88200(7) 0.0633(4) Uani 1.000000 .
C11 C 0.14071(18) 0.12503(9) 0.84986(7) 0.0638(4) Uani 1.000000 .
C12 C 0.55609(17) 0.43751(10) 0.67820(10) 0.0743(4) Uani 1.000000 .
C13 C 0.21553(19) 0.17320(10) 0.90174(7) 0.0689(4) Uani 1.000000 .
C14 C 0.51393(17) 0.39130(9) 0.79902(9) 0.0663(4) Uani 1.000000 .
C15 C 0.1616(2) 0.09632(12) 0.53744(8) 0.0823(5) Uani 1.000000 .
C16 C 0.46136(16) 0.37298(9) 0.65132(8) 0.0631(4) Uani 1.000000 .
C17 C 0.58226(18) 0.44643(10) 0.75065(11) 0.0758(5) Uani 1.000000 .
C18 C 0.3081(3) 0.05760(16) 0.51171(10) 0.1099(8) Uani 1.000000 .
H5 H 0.10580(15) 0.10952(8) 0.74364(7) 0.0658(4) Uiso 1.000000 R
H11 H 0.07671(18) 0.07964(9) 0.86397(7) 0.0766(5) Uiso 1.000000 R
H13 H 0.20174(19) 0.15995(10) 0.94983(7) 0.0827(5) Uiso 1.000000 R
H10 H 0.36028(18) 0.27353(10) 0.91658(7) 0.0759(5) Uiso 1.000000 R
H16 H 0.44418(16) 0.36742(9) 0.60249(8) 0.0757(5) Uiso 1.000000 R
H12 H 0.60345(17) 0.47595(10) 0.64662(10) 0.0892(5) Uiso 1.000000 R
H17 H 0.64701(18) 0.49036(10) 0.76686(11) 0.0909(5) Uiso 1.000000 R
H14 H 0.53165(17) 0.39750(9) 0.84776(9) 0.0795(5) Uiso 1.000000 R
H9a H 0.22060(17) 0.08515(10) 0.64329(7) 0.0732(4) Uiso 1.000000 R
H9b H 0.06773(17) 0.13580(10) 0.63269(7) 0.0732(4) Uiso 1.000000 R
H15a H 0.0828(2) 0.05208(12) 0.53382(8) 0.0987(6) Uiso 1.000000 R
H15b H 0.1338(2) 0.14503(12) 0.50656(8) 0.0987(6) Uiso 1.000000 R
H18a H 0.2980(7) 0.0404(12) 0.4626(3) 0.1648(11) Uiso 1.000000 GR
H18b H 0.3871(5) 0.1007(4) 0.5160(10) 0.1648(11) Uiso 1.000000 GR
H18c H 0.3330(11) 0.0070(8) 0.5401(7) 0.1648(11) 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
N1 C2 1.4248(14) . ?
N1 C4 1.3950(15) . ?
N1 C8 1.4241(16) . ?
C2 C3 1.4043(17) . ?
C2 C5 1.3872(18) . ?
C3 C6 1.4423(19) . ?
C3 C10 1.3922(18) . ?
C4 O1 1.2037(17) . ?
C4 C9 1.503(2) . ?
C5 C11 1.3834(18) . ?
C6 C8 1.3973(17) . ?
C6 C14 1.3894(19) . ?
C8 C16 1.3908(19) . ?
C9 C15 1.5229(19) . ?
C10 C13 1.373(2) . ?
C11 C13 1.384(2) . ?
C12 C16 1.384(2) . ?
C12 C17 1.382(3) . ?
C14 C17 1.373(2) . ?
C15 C18 1.502(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
C4 N1 C2 129.67(11) . . ?
C8 N1 C2 107.61(9) . . ?
C8 N1 C4 122.71(11) . . ?
C3 C2 N1 108.19(10) . . ?
C5 C2 N1 131.69(11) . . ?
C5 C2 C3 120.06(11) . . ?
C6 C3 C2 107.83(10) . . ?
C10 C3 C2 120.31(12) . . ?
C10 C3 C6 131.85(12) . . ?
O1 C4 N1 119.92(14) . . ?
C9 C4 N1 118.70(11) . . ?
C9 C4 O1 121.39(12) . . ?
C11 C5 C2 118.21(12) . . ?
C8 C6 C3 107.78(10) . . ?
C14 C6 C3 131.96(13) . . ?
C14 C6 C8 120.26(13) . . ?
C6 C8 N1 108.57(11) . . ?
C16 C8 N1 130.32(12) . . ?
C16 C8 C6 121.10(12) . . ?
C15 C9 C4 112.82(12) . . ?
C13 C10 C3 119.45(13) . . ?
C13 C11 C5 122.15(14) . . ?
C17 C12 C16 121.82(15) . . ?
C11 C13 C10 119.79(13) . . ?
C17 C14 C6 118.62(15) . . ?
C18 C15 C9 112.94(14) . . ?
C12 C16 C8 117.32(14) . . ?
C14 C17 C12 120.88(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 1.212
_oxdiff_exptl_absorpt_empirical_full_min 0.664
####################################################################### 
# 
# 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_Cz-6
_database_code_depnum_ccdc_archive 'CCDC 2050876'
loop_
_audit_author_name
_audit_author_address
Tulianjing
;Institute of Molecular Aggregation Science, Tianjin University
China
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-07-18 downloaded from the CCDC.
;
_audit_creation_date             2019-12-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C18 H19 N O'
_chemical_formula_sum            'C18 H19 N O'
_chemical_formula_weight         265.36
_chemical_oxdiff_formula         C18H19ON
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      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y,-z+1/2
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y+1/2,z
5 -x,-y,-z
6 -x-1/2,y,z-1/2
7 x,-y-1/2,z-1/2
8 x-1/2,y-1/2,-z

_symmetry_Int_Tables_number      56
_cell_length_a                   24.8983(2)
_cell_length_b                   16.9181(2)
_cell_length_c                   6.91920(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2914.59(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    23600
_cell_measurement_temperature    300
_cell_measurement_theta_max      72.9950
_cell_measurement_theta_min      5.2950
_exptl_absorpt_coefficient_mu    0.579
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.2094
_exptl_crystal_description       needle
_exptl_crystal_F_000             1139.2761
_exptl_crystal_preparation       'solvent evaporation'
_exptl_crystal_recrystallization_method ?
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            44542
_diffrn_reflns_theta_full        67.0609
_diffrn_reflns_theta_max         67.06
_diffrn_reflns_theta_min         3.55
_diffrn_ambient_temperature      300
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.9996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  17.00   1.00    2.59    --   34.00 101.00-173.40   25
  2  ω   -116.00 -18.00   1.00    2.59    --  -41.12 -37.00 120.00   98
  3  ω    -64.00  31.00   1.00    2.59    --  -41.12  37.00 120.00   95
  4  ω    -82.00 -17.00   1.00    2.59    --  -41.12 -37.00-120.00   65
  5  ω   -115.00 -17.00   1.00    2.59    --  -41.12 -37.00   0.00   98
  6  ω     29.00  92.00   1.00    2.59    --   41.12-125.00  30.00   63
  7  ω     25.00  92.00   1.00    2.59    --   41.12-125.00-120.00   67
  8  ω     24.00  77.00   1.00    2.59    --   41.12-125.00 -90.00   53
  9  ω     12.00  38.00   1.00    2.59    --   46.00  84.00 -95.87   26
 10  ω     12.00  38.00   1.00    2.59    --   46.00  83.00  50.18   26
 11  ω     16.00  41.00   1.00    2.59    --   50.00  82.00 -38.62   25
 12  ω     16.00  41.00   1.00    2.59    --   50.00  82.00-170.25   25
 13  ω    107.00 133.00   1.00    2.59    --   58.00  77.00 139.79   26
 14  ω     89.00 132.00   1.00    2.59    --   58.00  75.00  19.49   43
 15  ω     25.00  56.00   1.00    2.59    --   58.00  77.00  74.14   31
 16  ω     25.00  77.00   1.00    2.59    --   58.00  77.00 139.79   52
 17  ω     32.00  59.00   1.00    2.59    --   58.00  75.00  19.49   27
 18  ω     89.00 129.00   1.00    2.59    --   58.00  77.00  74.14   40
 19  ω     92.00 119.00   1.00    2.59    --   62.00  75.00 -54.22   27
 20  ω     30.00  56.00   1.00    2.59    --   62.00  75.00 -54.22   26
 21  ω     86.00 113.00   1.00    2.59    --   62.00  77.00 -22.23   27
 22  ω     30.00  76.00   1.00    2.59    --   62.00  77.00 -22.23   46
 23  ω     34.00  77.00   1.00    2.59    --   66.00  75.00 -43.37   43
 24  ω     34.00  60.00   1.00    2.59    --   66.00  76.00-134.10   26
 25  ω     33.00  62.00   1.00    2.59    --   66.00  77.00-161.55   29
 26  ω     37.00  78.00   1.00    2.59    --   70.00  77.00  94.41   41
 27  ω     37.00  68.00   1.00    2.59    --   70.00  77.00-109.64   31
 28  ω     77.00 174.00   1.00   10.34    --  105.32  61.00 120.00   97
 29  ω     80.00 106.00   1.00   10.34    --  105.32 -94.00 -30.00   26
 30  ω     73.00 177.00   1.00   10.34    --  105.32  77.00  60.00  104
 31  ω     73.00  99.00   1.00   10.34    --  105.32  77.00   0.00   26
 32  ω     76.00 102.00   1.00   10.34    --  105.32  61.00 -30.00   26
 33  ω     33.00 134.00   1.00   10.34    --  105.32 -61.00  90.00  101
 34  ω     78.00 109.00   1.00   10.34    --  105.32-106.00-177.00   31
 35  ω     73.00  99.00   1.00   10.34    --  105.32  77.00 120.00   26
 36  ω     73.00 178.00   1.00   10.34    --  105.32  77.00 150.00  105
 37  ω     76.00 102.00   1.00   10.34    --  105.32  61.00 150.00   26
 38  ω     31.00 109.00   1.00   10.34    --  105.32 -94.00  60.00   78
 39  ω     77.00 116.00   1.00   10.34    --  105.32  61.00  30.00   39
 40  ω    122.00 167.00   1.00   10.34    --  105.32  77.00  90.00   45
 41  ω     79.00 105.00   1.00   10.34    --  105.32  61.00  90.00   26
 42  ω     73.00  99.00   1.00   10.34    --  105.32  77.00  90.00   26
 43  ω     73.00 171.00   1.00   10.34    --  105.32  77.00 -60.00   98
 44  ω     76.00 111.00   1.00   10.34    --  105.32  61.00 -90.00   35
 45  ω    122.00 151.00   1.00   10.34    --  105.32  77.00 -30.00   29
 46  ω     73.00  99.00   1.00   10.34    --  105.32  77.00 -30.00   26
 47  ω    118.00 154.00   1.00   10.34    --  105.32  77.00-120.00   36
 48  ω     73.00 171.00   1.00   10.34    --  105.32  77.00  30.00   98
 49  ω     73.00  98.00   1.00   10.34    --  105.32  77.00-120.00   25
 50  ω     73.00 149.00   1.00   10.34    --  105.32  77.00-180.00   76
 51  ω     38.00 134.00   1.00   10.34    --  105.32 -77.00-120.00   96
 52  ω     77.00 178.00   1.00   10.34    --  105.32  61.00   0.00  101
 53  ω     73.00 177.00   1.00   10.34    --  105.32  77.00-150.00  104
 54  ω     73.00 154.00   1.00   10.34    --  105.32  77.00 -90.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0359659000
_diffrn_orient_matrix_UB_12      -0.0665938000
_diffrn_orient_matrix_UB_13      0.0789988000
_diffrn_orient_matrix_UB_21      -0.0478303000
_diffrn_orient_matrix_UB_22      0.0577481000
_diffrn_orient_matrix_UB_23      0.0088195000
_diffrn_orient_matrix_UB_31      -0.0157537000
_diffrn_orient_matrix_UB_32      -0.0228787000
_diffrn_orient_matrix_UB_33      -0.2079426000
_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              29
_reflns_limit_h_min              0
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              8
_reflns_limit_l_min              0
_reflns_number_gt                2422
_reflns_number_total             2599
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.1789
_refine_diff_density_min         -0.3330
_refine_diff_density_rms         0.0846
_refine_ls_d_res_high            0.8371
_refine_ls_d_res_low             12.4491
_refine_ls_goodness_of_fit_ref   1.0493
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2599
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      1.0493
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0757P)²+0.5189P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1354
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b), C7(H7a,H7b), C9(H9a,H9b), C15(H15a,H15b)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C18(H18), C11(H11), C16(H16), C14(H14), C20(H20), C17(H17)
2.c Idealised Me refined as rotating group:
 C19(H19a,H19b,H19c)
;
_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_refinement_flags_posn
N1 N 0.37375(5) 0.55461(6) 0.23943(17) 0.0541(3) Uani 1.000000 .
O1 O 0.40911(6) 0.67349(6) 0.1650(2) 0.0916(5) Uani 1.000000 .
C3 C 0.43142(6) 0.57160(8) -0.0547(2) 0.0552(4) Uani 1.000000 .
C4 C 0.34963(5) 0.58035(8) 0.4148(2) 0.0545(4) Uani 1.000000 .
C5 C 0.32169(5) 0.51671(9) 0.4965(2) 0.0596(4) Uani 1.000000 .
C6 C 0.40461(6) 0.60467(8) 0.1215(2) 0.0583(4) Uani 1.000000 .
C7 C 0.49263(6) 0.60040(8) -0.3384(2) 0.0577(4) Uani 1.000000 .
C8 C 0.35907(6) 0.47383(8) 0.2115(2) 0.0565(4) Uani 1.000000 .
C9 C 0.46719(6) 0.63170(8) -0.1550(2) 0.0588(4) Uani 1.000000 .
C10 C 0.32767(5) 0.45026(9) 0.3692(2) 0.0600(4) Uani 1.000000 .
C11 C 0.29389(6) 0.52679(12) 0.6691(3) 0.0746(5) Uani 1.000000 .
C12 C 0.35069(6) 0.65359(10) 0.5048(2) 0.0636(4) Uani 1.000000 .
C13 C 0.32187(7) 0.66186(11) 0.6745(2) 0.0738(5) Uani 1.000000 .
C14 C 0.34942(8) 0.34527(10) 0.0760(3) 0.0812(5) Uani 1.000000 .
C15 C 0.52630(7) 0.66170(10) -0.4418(3) 0.0737(5) Uani 1.000000 .
C16 C 0.37023(7) 0.42111(9) 0.0631(3) 0.0708(5) Uani 1.000000 .
C17 C 0.30688(7) 0.37338(10) 0.3772(3) 0.0764(5) Uani 1.000000 .
C18 C 0.29367(7) 0.59960(13) 0.7565(3) 0.0801(5) Uani 1.000000 .
C19 C 0.55150(8) 0.63199(12) -0.6265(3) 0.0838(5) Uani 1.000000 .
C20 C 0.31811(7) 0.32158(10) 0.2295(3) 0.0825(6) Uani 1.000000 .
H12 H 0.37005(6) 0.69555(10) 0.4530(2) 0.0763(5) Uiso 1.000000 R
H13 H 0.32138(7) 0.71080(11) 0.7357(2) 0.0886(6) Uiso 1.000000 R
H18 H 0.27463(7) 0.60720(13) 0.8706(3) 0.0961(6) Uiso 1.000000 R
H11 H 0.27561(6) 0.48460(12) 0.7247(3) 0.0895(6) Uiso 1.000000 R
H16 H 0.39110(7) 0.43623(9) -0.0420(3) 0.0850(5) Uiso 1.000000 R
H14 H 0.35684(8) 0.30929(10) -0.0221(3) 0.0975(6) Uiso 1.000000 R
H20 H 0.30452(7) 0.27040(10) 0.2332(3) 0.0990(7) Uiso 1.000000 R
H17 H 0.28574(7) 0.35759(10) 0.4811(3) 0.0916(6) Uiso 1.000000 R
H3a H 0.45289(6) 0.52620(8) -0.0178(2) 0.0662(4) Uiso 1.000000 R
H3b H 0.40414(6) 0.55363(8) -0.1446(2) 0.0662(4) Uiso 1.000000 R
H7a H 0.51508(6) 0.55538(8) -0.3067(2) 0.0693(4) Uiso 1.000000 R
H7b H 0.46454(6) 0.58220(8) -0.4248(2) 0.0693(4) Uiso 1.000000 R
H9a H 0.44602(6) 0.67812(8) -0.1861(2) 0.0706(5) Uiso 1.000000 R
H9b H 0.49537(6) 0.64786(8) -0.0666(2) 0.0706(5) Uiso 1.000000 R
H15a H 0.50388(7) 0.70698(10) -0.4715(3) 0.0884(6) Uiso 1.000000 R
H15b H 0.55455(7) 0.67941(10) -0.3555(3) 0.0884(6) Uiso 1.000000 R
H19a H 0.52379(9) 0.6159(9) -0.7147(9) 0.1257(8) Uiso 1.000000 GR
H19b H 0.5724(5) 0.6734(3) -0.6841(12) 0.1257(8) Uiso 1.000000 GR
H19c H 0.5743(5) 0.5877(6) -0.5983(4) 0.1257(8) 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
N1 C4 1.4224(19) . ?
N1 C6 1.4047(18) . ?
N1 C8 1.4278(17) . ?
O1 C6 1.2076(17) . ?
C3 C6 1.498(2) . ?
C3 C9 1.5195(19) . ?
C4 C5 1.4011(19) . ?
C4 C12 1.387(2) . ?
C5 C10 1.436(2) . ?
C5 C11 1.391(2) . ?
C7 C9 1.514(2) . ?
C7 C15 1.513(2) . ?
C8 C10 1.401(2) . ?
C8 C16 1.388(2) . ?
C10 C17 1.401(2) . ?
C11 C18 1.372(3) . ?
C12 C13 1.383(2) . ?
C13 C18 1.387(2) . ?
C14 C16 1.387(2) . ?
C14 C20 1.377(3) . ?
C15 C19 1.510(2) . ?
C17 C20 1.375(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
C6 N1 C4 122.81(11) . . ?
C8 N1 C4 107.50(11) . . ?
C8 N1 C6 129.67(13) . . ?
C9 C3 C6 112.52(12) . . ?
C5 C4 N1 108.58(13) . . ?
C12 C4 N1 130.44(13) . . ?
C12 C4 C5 120.98(14) . . ?
C10 C5 C4 107.62(13) . . ?
C11 C5 C4 119.96(15) . . ?
C11 C5 C10 132.40(14) . . ?
O1 C6 N1 119.18(14) . . ?
C3 C6 N1 119.41(12) . . ?
C3 C6 O1 121.41(13) . . ?
C15 C7 C9 112.85(13) . . ?
C10 C8 N1 108.04(13) . . ?
C16 C8 N1 131.61(14) . . ?
C16 C8 C10 120.35(14) . . ?
C7 C9 C3 113.21(12) . . ?
C8 C10 C5 108.25(12) . . ?
C17 C10 C5 131.63(16) . . ?
C17 C10 C8 120.08(16) . . ?
C18 C11 C5 119.36(15) . . ?
C13 C12 C4 117.50(15) . . ?
C18 C13 C12 122.19(17) . . ?
C20 C14 C16 122.03(19) . . ?
C19 C15 C7 113.71(15) . . ?
C14 C16 C8 118.19(17) . . ?
C20 C17 C10 119.16(17) . . ?
C13 C18 C11 119.98(17) . . ?
C17 C20 C14 120.19(15) . . ?

_olex2_date_sample_data_collection 2019-12-27
_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 2.023
_oxdiff_exptl_absorpt_empirical_full_min 0.373
