# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2020
#######################################################################
#
# 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_wtl-zlx-p1
_database_code_depnum_ccdc_archive 'CCDC 2004465'
loop_
_audit_author_name
_audit_author_address
zlx
;zlx
China
;
_audit_update_record
;
2020-05-18 deposited with the CCDC. 2020-09-03 downloaded from the CCDC.
;
_audit_creation_date 2019-06-03
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C21 H17 N O2'
_chemical_formula_sum 'C21 H17 N O2'
_chemical_formula_weight 315.36
_chemical_absolute_configuration ad
_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 orthorhombic
_space_group_IT_number 19
_space_group_name_H-M_alt 'P 21 21 21'
_space_group_name_Hall 'P 2ac 2ab'
loop_
_space_group_symop_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'
_cell_length_a 9.61101(18)
_cell_length_b 10.7261(2)
_cell_length_c 15.5952(3)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 1607.68(6)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 3753
_cell_measurement_temperature 296.63(16)
_cell_measurement_theta_max 71.4930
_cell_measurement_theta_min 4.9450
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.667
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.64614
_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 yellowish yellow'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier yellowish
_exptl_crystal_colour_primary yellow
_exptl_crystal_density_diffrn 1.303
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 664
_exptl_crystal_size_max 0.5
_exptl_crystal_size_mid 0.3
_exptl_crystal_size_min 0.3
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0400
_diffrn_reflns_av_unetI/netI 0.0366
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_number 8852
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full 67.684
_diffrn_reflns_theta_max 71.704
_diffrn_reflns_theta_min 5.004
_diffrn_ambient_environment air
_diffrn_ambient_temperature 296.63(16)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):
# Type Start End Width t~exp~ \w \q \k \f Frames
#--------------------------------------------------------------------------
1 \w -53.00 31.00 1.00 1.00 -- -36.29 57.00 -60.00 84
2 \w -106.00 33.00 1.00 1.00 -- -36.29 0.00 -60.00 139
3 \w 1.00 75.00 1.00 1.00 -- 36.29 -99.00-120.00 74
4 \w 88.00 173.00 1.00 1.61 -- 106.21 61.00 0.00 85
5 \w 79.00 174.00 1.00 1.61 -- 106.21 77.00 90.00 95
6 \w 37.00 109.00 1.00 1.61 -- 106.21 -94.00 0.00 72
7 \w 89.00 175.00 1.00 1.61 -- 106.21 45.00 120.00 86
8 \w 39.00 124.00 1.00 1.61 -- 106.21 -61.00 150.00 85
9 \w 68.00 177.00 1.00 1.61 -- 106.21 15.00-120.00 109
10 \w 37.00 109.00 1.00 1.61 -- 106.21 -94.00-120.00 72
11 \w 57.00 150.00 1.00 1.61 -- 106.21 178.00 30.00 93
12 \w -104.00 -10.00 1.00 1.00 -- -36.29 -77.00-150.00 94
13 \w -31.00 22.00 1.00 1.00 -- 36.29 -57.00 60.00 53
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 -0.0829550000
_diffrn_orient_matrix_UB_12 -0.1227356000
_diffrn_orient_matrix_UB_13 0.0044948000
_diffrn_orient_matrix_UB_21 -0.0018229000
_diffrn_orient_matrix_UB_22 -0.0066307000
_diffrn_orient_matrix_UB_23 -0.0986731000
_diffrn_orient_matrix_UB_31 0.1371814000
_diffrn_orient_matrix_UB_32 -0.0742450000
_diffrn_orient_matrix_UB_33 0.0014005000
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source 'fine-focus sealed X-ray tube'
_diffrn_source_type 'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage 0.719
_reflns_Friedel_fraction_full 1.000
_reflns_Friedel_fraction_max 0.970
_reflns_number_gt 2935
_reflns_number_total 3096
_reflns_odcompleteness_completeness 99.94
_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 > 2\s(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 0.333
_refine_diff_density_min -0.628
_refine_diff_density_rms 0.162
_refine_ls_abs_structure_details
;
Flack x determined using 1167 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack -0.03(16)
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.115
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 217
_refine_ls_number_reflns 3096
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0748
_refine_ls_R_factor_gt 0.0726
_refine_ls_restrained_S_all 1.115
_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/[\s^2^(Fo^2^)+(0.1206P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1591
_refine_ls_wR_factor_ref 0.1640
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
C008(H008), C009(H009)
2.b Aromatic/amide H refined with riding coordinates:
N003(H003), C005(H005), C00A(H00A), C00B(H00B), C00D(H00D), C00E(H00E),
C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
C00M(H00M), C00N(H00N), C00O(H00O)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_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 -0.1707(2) -0.6481(2) -0.32731(13) 0.0464(5) Uani 1 1 d . . . . .
O002 O -0.0242(2) -0.5569(2) -0.45917(17) 0.0546(6) Uani 1 1 d . . . . .
N003 N -0.3160(3) -0.7274(2) -0.47375(14) 0.0410(5) Uani 1 1 d . . . . .
H003 H -0.3416 -0.7405 -0.5258 0.049 Uiso 1 1 calc R . . . .
C004 C -0.1389(3) -0.5121(3) -0.45073(18) 0.0400(6) Uani 1 1 d . . . . .
C005 C -0.5434(3) -0.7641(3) -0.35465(19) 0.0446(6) Uani 1 1 d . . . . .
H005 H -0.5077 -0.8302 -0.3863 0.053 Uiso 1 1 calc R . . . .
C006 C -0.4840(3) -0.6475(2) -0.36191(16) 0.0353(6) Uani 1 1 d . . . . .
C007 C -0.1869(3) -0.4075(2) -0.50606(18) 0.0389(6) Uani 1 1 d . . . . .
C008 C -0.2387(3) -0.5622(3) -0.38269(16) 0.0385(6) Uani 1 1 d . . . . .
H008 H -0.2709 -0.4916 -0.3480 0.046 Uiso 1 1 calc R . . . .
C009 C -0.3672(3) -0.6219(3) -0.42597(16) 0.0363(6) Uani 1 1 d . . . . .
H009 H -0.4029 -0.5615 -0.4677 0.044 Uiso 1 1 calc R . . . .
C00A C -0.2922(4) -0.3259(3) -0.4817(2) 0.0500(7) Uani 1 1 d . . . . .
H00A H -0.3373 -0.3368 -0.4294 0.060 Uiso 1 1 calc R . . . .
C00B C -0.6484(3) -0.5701(4) -0.2576(2) 0.0544(8) Uani 1 1 d . . . . .
H00B H -0.6833 -0.5045 -0.2251 0.065 Uiso 1 1 calc R . . . .
C00C C -0.2236(3) -0.8074(3) -0.43251(18) 0.0407(6) Uani 1 1 d . . . . .
C00D C -0.1226(4) -0.3904(3) -0.58538(19) 0.0498(7) Uani 1 1 d . . . . .
H00D H -0.0524 -0.4444 -0.6028 0.060 Uiso 1 1 calc R . . . .
C00E C -0.5377(3) -0.5505(3) -0.3125(2) 0.0462(7) Uani 1 1 d . . . . .
H00E H -0.4984 -0.4715 -0.3165 0.055 Uiso 1 1 calc R . . . .
C00F C -0.1995(3) -0.9278(3) -0.4615(2) 0.0511(7) Uani 1 1 d . . . . .
H00F H -0.2483 -0.9577 -0.5087 0.061 Uiso 1 1 calc R . . . .
C00G C -0.1493(3) -0.7648(3) -0.36108(19) 0.0430(6) Uani 1 1 d . . . . .
C00H C -0.2662(4) -0.2128(3) -0.6133(2) 0.0608(9) Uani 1 1 d . . . . .
H00H H -0.2929 -0.1478 -0.6491 0.073 Uiso 1 1 calc R . . . .
C00I C -0.1032(4) -1.0041(3) -0.4209(3) 0.0625(10) Uani 1 1 d . . . . .
H00I H -0.0878 -1.0844 -0.4414 0.075 Uiso 1 1 calc R . . . .
C00J C -0.3301(4) -0.2280(3) -0.5353(3) 0.0605(9) Uani 1 1 d . . . . .
H00J H -0.3991 -0.1726 -0.5182 0.073 Uiso 1 1 calc R . . . .
C00K C -0.0532(3) -0.8419(4) -0.3205(2) 0.0577(9) Uani 1 1 d . . . . .
H00K H -0.0041 -0.8130 -0.2732 0.069 Uiso 1 1 calc R . . . .
C00L C -0.7072(4) -0.6871(4) -0.2511(2) 0.0573(8) Uani 1 1 d . . . . .
H00L H -0.7810 -0.7008 -0.2136 0.069 Uiso 1 1 calc R . . . .
C00M C -0.1633(4) -0.2929(4) -0.6384(2) 0.0609(9) Uani 1 1 d . . . . .
H00M H -0.1204 -0.2821 -0.6914 0.073 Uiso 1 1 calc R . . . .
C00N C -0.6561(3) -0.7838(3) -0.3005(2) 0.0560(8) Uani 1 1 d . . . . .
H00N H -0.6971 -0.8622 -0.2975 0.067 Uiso 1 1 calc R . . . .
C00O C -0.0306(4) -0.9620(4) -0.3507(3) 0.0686(11) Uani 1 1 d . . . . .
H00O H 0.0334 -1.0136 -0.3236 0.082 Uiso 1 1 calc R . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O001 0.0425(11) 0.0544(12) 0.0423(9) 0.0031(9) -0.0082(8) -0.0026(9)
O002 0.0375(12) 0.0520(12) 0.0744(14) 0.0058(10) 0.0108(10) 0.0023(10)
N003 0.0380(12) 0.0487(13) 0.0365(10) -0.0029(9) -0.0014(9) -0.0005(10)
C004 0.0326(14) 0.0398(13) 0.0475(14) -0.0058(11) 0.0035(11) -0.0045(11)
C005 0.0406(14) 0.0459(14) 0.0473(14) -0.0015(11) 0.0025(12) -0.0068(12)
C006 0.0279(12) 0.0434(13) 0.0346(11) 0.0039(10) -0.0031(9) 0.0028(10)
C007 0.0353(13) 0.0355(12) 0.0461(13) -0.0041(10) 0.0062(11) -0.0073(10)
C008 0.0334(14) 0.0424(14) 0.0395(12) -0.0012(10) -0.0001(10) -0.0026(11)
C009 0.0319(13) 0.0414(13) 0.0357(11) 0.0044(10) 0.0015(10) -0.0005(10)
C00A 0.0461(17) 0.0444(14) 0.0596(17) 0.0033(13) 0.0133(14) -0.0001(13)
C00B 0.0408(16) 0.0628(19) 0.0597(17) -0.0040(15) 0.0098(13) 0.0108(14)
C00C 0.0305(13) 0.0475(15) 0.0440(13) 0.0050(11) 0.0085(11) -0.0010(11)
C00D 0.0541(17) 0.0500(16) 0.0454(14) -0.0064(12) 0.0108(14) -0.0020(14)
C00E 0.0397(15) 0.0433(15) 0.0556(16) 0.0022(12) 0.0066(13) 0.0044(12)
C00F 0.0407(16) 0.0493(16) 0.0634(17) -0.0024(13) 0.0152(14) -0.0013(14)
C00G 0.0322(13) 0.0496(15) 0.0473(13) 0.0081(12) 0.0029(11) -0.0041(11)
C00H 0.068(2) 0.0513(18) 0.0630(19) 0.0114(15) -0.0059(16) -0.0061(16)
C00I 0.0456(18) 0.0505(19) 0.091(3) 0.0084(18) 0.0246(19) 0.0065(15)
C00J 0.0491(19) 0.0442(16) 0.088(2) 0.0085(16) 0.0080(17) 0.0056(14)
C00K 0.0341(15) 0.072(2) 0.0672(19) 0.0223(17) -0.0074(14) -0.0049(15)
C00L 0.0403(16) 0.077(2) 0.0552(16) 0.0059(16) 0.0109(13) -0.0039(15)
C00M 0.080(2) 0.0589(19) 0.0441(14) 0.0030(14) 0.0092(16) -0.0087(18)
C00N 0.0499(19) 0.0543(17) 0.0637(18) 0.0037(15) 0.0114(15) -0.0142(14)
C00O 0.0426(18) 0.062(2) 0.101(3) 0.030(2) 0.0105(19) 0.0109(15)
_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 C008 1.422(3) . ?
O001 C00G 1.374(4) . ?
O002 C004 1.210(4) . ?
N003 H003 0.8600 . ?
N003 C009 1.442(4) . ?
N003 C00C 1.392(4) . ?
C004 C007 1.488(4) . ?
C004 C008 1.528(4) . ?
C005 H005 0.9300 . ?
C005 C006 1.379(4) . ?
C005 C00N 1.389(4) . ?
C006 C009 1.528(3) . ?
C006 C00E 1.394(4) . ?
C007 C00A 1.391(4) . ?
C007 C00D 1.395(4) . ?
C008 H008 0.9800 . ?
C008 C009 1.546(4) . ?
C009 H009 0.9800 . ?
C00A H00A 0.9300 . ?
C00A C00J 1.391(5) . ?
C00B H00B 0.9300 . ?
C00B C00E 1.382(4) . ?
C00B C00L 1.380(5) . ?
C00C C00F 1.389(4) . ?
C00C C00G 1.400(4) . ?
C00D H00D 0.9300 . ?
C00D C00M 1.390(5) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00F C00I 1.388(5) . ?
C00G C00K 1.392(4) . ?
C00H H00H 0.9300 . ?
C00H C00J 1.372(6) . ?
C00H C00M 1.367(6) . ?
C00I H00I 0.9300 . ?
C00I C00O 1.375(6) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00K C00O 1.388(6) . ?
C00L H00L 0.9300 . ?
C00L C00N 1.382(5) . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9300 . ?
C00O H00O 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
C00G O001 C008 115.2(2) . . ?
C009 N003 H003 121.2 . . ?
C00C N003 H003 121.2 . . ?
C00C N003 C009 117.5(2) . . ?
O002 C004 C007 121.3(3) . . ?
O002 C004 C008 120.5(3) . . ?
C007 C004 C008 118.2(2) . . ?
C006 C005 H005 119.7 . . ?
C006 C005 C00N 120.7(3) . . ?
C00N C005 H005 119.7 . . ?
C005 C006 C009 121.4(3) . . ?
C005 C006 C00E 118.6(3) . . ?
C00E C006 C009 119.9(2) . . ?
C00A C007 C004 122.8(3) . . ?
C00A C007 C00D 118.8(3) . . ?
C00D C007 C004 118.4(3) . . ?
O001 C008 C004 111.1(2) . . ?
O001 C008 H008 108.0 . . ?
O001 C008 C009 111.3(2) . . ?
C004 C008 H008 108.0 . . ?
C004 C008 C009 110.1(2) . . ?
C009 C008 H008 108.0 . . ?
N003 C009 C006 116.6(2) . . ?
N003 C009 C008 106.2(2) . . ?
N003 C009 H009 107.2 . . ?
C006 C009 C008 112.1(2) . . ?
C006 C009 H009 107.2 . . ?
C008 C009 H009 107.2 . . ?
C007 C00A H00A 120.0 . . ?
C00J C00A C007 120.1(3) . . ?
C00J C00A H00A 120.0 . . ?
C00E C00B H00B 120.0 . . ?
C00L C00B H00B 120.0 . . ?
C00L C00B C00E 120.0(3) . . ?
N003 C00C C00G 119.5(3) . . ?
C00F C00C N003 122.0(3) . . ?
C00F C00C C00G 118.5(3) . . ?
C007 C00D H00D 119.9 . . ?
C00M C00D C007 120.2(3) . . ?
C00M C00D H00D 119.9 . . ?
C006 C00E H00E 119.5 . . ?
C00B C00E C006 120.9(3) . . ?
C00B C00E H00E 119.5 . . ?
C00C C00F H00F 119.6 . . ?
C00I C00F C00C 120.8(4) . . ?
C00I C00F H00F 119.6 . . ?
O001 C00G C00C 121.7(3) . . ?
O001 C00G C00K 117.8(3) . . ?
C00K C00G C00C 120.4(3) . . ?
C00J C00H H00H 119.9 . . ?
C00M C00H H00H 119.9 . . ?
C00M C00H C00J 120.2(3) . . ?
C00F C00I H00I 119.7 . . ?
C00O C00I C00F 120.5(4) . . ?
C00O C00I H00I 119.7 . . ?
C00A C00J H00J 119.8 . . ?
C00H C00J C00A 120.4(3) . . ?
C00H C00J H00J 119.8 . . ?
C00G C00K H00K 120.0 . . ?
C00O C00K C00G 120.1(4) . . ?
C00O C00K H00K 120.0 . . ?
C00B C00L H00L 120.2 . . ?
C00B C00L C00N 119.7(3) . . ?
C00N C00L H00L 120.2 . . ?
C00D C00M H00M 119.8 . . ?
C00H C00M C00D 120.4(3) . . ?
C00H C00M H00M 119.8 . . ?
C005 C00N H00N 119.9 . . ?
C00L C00N C005 120.1(3) . . ?
C00L C00N H00N 119.9 . . ?
C00I C00O C00K 119.7(3) . . ?
C00I C00O H00O 120.1 . . ?
C00K C00O H00O 120.1 . . ?
_shelx_res_file
;
wtl-zlx-p1.res created by SHELXL-2014/7
TITL wtl-zlx-p1_a.res in P2(1)2(1)2(1)
REM Old TITL wtl-zlx-p1 in P212121 #19
REM SHELXT solution in P2(1)2(1)2(1)
REM R1 0.159, Rweak 0.056, Alpha 0.002, Orientation as input
REM Flack x = 0.341 ( 0.379 ) from Parsons' quotients
REM Formula found by SHELXT: C21 N O2
CELL 1.54184 9.611009 10.726079 15.595198 90 90 90
ZERR 4 0.000184 0.000234 0.000321 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H N O
UNIT 84 68 4 8
L.S. 10
PLAN 20
BOND $H
LIST 6
fmap 2
ACTA
REM
REM
REM
WGHT 0.120600
FVAR 12.54419
O001 4 -0.170692 -0.648050 -0.327310 11.00000 0.04247 0.05438 =
0.04235 0.00313 -0.00821 -0.00265
O002 4 -0.024161 -0.556923 -0.459168 11.00000 0.03748 0.05198 =
0.07437 0.00581 0.01082 0.00228
N003 3 -0.316002 -0.727442 -0.473750 11.00000 0.03795 0.04868 =
0.03647 -0.00293 -0.00143 -0.00050
AFIX 43
H003 2 -0.341622 -0.740530 -0.525814 11.00000 -1.20000
AFIX 0
C004 1 -0.138875 -0.512054 -0.450733 11.00000 0.03263 0.03984 =
0.04752 -0.00581 0.00354 -0.00454
C005 1 -0.543406 -0.764055 -0.354645 11.00000 0.04059 0.04588 =
0.04727 -0.00154 0.00246 -0.00685
AFIX 43
H005 2 -0.507674 -0.830162 -0.386332 11.00000 -1.20000
AFIX 0
C006 1 -0.484023 -0.647499 -0.361910 11.00000 0.02795 0.04343 =
0.03463 0.00393 -0.00307 0.00281
C007 1 -0.186864 -0.407513 -0.506056 11.00000 0.03529 0.03545 =
0.04608 -0.00413 0.00620 -0.00732
C008 1 -0.238747 -0.562154 -0.382687 11.00000 0.03345 0.04244 =
0.03947 -0.00116 -0.00006 -0.00264
AFIX 13
H008 2 -0.270851 -0.491619 -0.347989 11.00000 -1.20000
AFIX 0
C009 1 -0.367157 -0.621870 -0.425966 11.00000 0.03187 0.04144 =
0.03566 0.00443 0.00154 -0.00052
AFIX 13
H009 2 -0.402856 -0.561477 -0.467673 11.00000 -1.20000
AFIX 0
C00A 1 -0.292189 -0.325894 -0.481659 11.00000 0.04606 0.04438 =
0.05962 0.00328 0.01325 -0.00013
AFIX 43
H00A 2 -0.337295 -0.336804 -0.429437 11.00000 -1.20000
AFIX 0
C00B 1 -0.648412 -0.570130 -0.257607 11.00000 0.04083 0.06280 =
0.05971 -0.00398 0.00980 0.01079
AFIX 43
H00B 2 -0.683282 -0.504525 -0.225074 11.00000 -1.20000
AFIX 0
C00C 1 -0.223648 -0.807360 -0.432507 11.00000 0.03052 0.04749 =
0.04404 0.00495 0.00853 -0.00099
C00D 1 -0.122645 -0.390393 -0.585383 11.00000 0.05411 0.04999 =
0.04537 -0.00642 0.01080 -0.00200
AFIX 43
H00D 2 -0.052408 -0.444372 -0.602823 11.00000 -1.20000
AFIX 0
C00E 1 -0.537684 -0.550492 -0.312474 11.00000 0.03969 0.04329 =
0.05558 0.00220 0.00664 0.00438
AFIX 43
H00E 2 -0.498414 -0.471463 -0.316476 11.00000 -1.20000
AFIX 0
C00F 1 -0.199466 -0.927831 -0.461524 11.00000 0.04073 0.04929 =
0.06341 -0.00239 0.01520 -0.00127
AFIX 43
H00F 2 -0.248333 -0.957730 -0.508708 11.00000 -1.20000
AFIX 0
C00G 1 -0.149339 -0.764820 -0.361080 11.00000 0.03219 0.04958 =
0.04730 0.00809 0.00286 -0.00405
C00H 1 -0.266167 -0.212776 -0.613277 11.00000 0.06796 0.05132 =
0.06304 0.01141 -0.00586 -0.00606
AFIX 43
H00H 2 -0.292889 -0.147755 -0.649125 11.00000 -1.20000
AFIX 0
C00I 1 -0.103229 -1.004119 -0.420932 11.00000 0.04557 0.05050 =
0.09149 0.00836 0.02457 0.00645
AFIX 43
H00I 2 -0.087750 -1.084383 -0.441369 11.00000 -1.20000
AFIX 0
C00J 1 -0.330094 -0.228003 -0.535284 11.00000 0.04914 0.04421 =
0.08822 0.00849 0.00800 0.00559
AFIX 43
H00J 2 -0.399134 -0.172565 -0.518196 11.00000 -1.20000
AFIX 0
C00K 1 -0.053220 -0.841904 -0.320538 11.00000 0.03414 0.07172 =
0.06723 0.02227 -0.00739 -0.00489
AFIX 43
H00K 2 -0.004103 -0.812961 -0.273171 11.00000 -1.20000
AFIX 0
C00L 1 -0.707243 -0.687084 -0.251089 11.00000 0.04031 0.07657 =
0.05515 0.00591 0.01094 -0.00393
AFIX 43
H00L 2 -0.780980 -0.700800 -0.213643 11.00000 -1.20000
AFIX 0
C00M 1 -0.163334 -0.292879 -0.638440 11.00000 0.07982 0.05887 =
0.04407 0.00300 0.00922 -0.00866
AFIX 43
H00M 2 -0.120371 -0.282058 -0.691353 11.00000 -1.20000
AFIX 0
C00N 1 -0.656064 -0.783772 -0.300481 11.00000 0.04990 0.05431 =
0.06366 0.00368 0.01140 -0.01415
AFIX 43
H00N 2 -0.697113 -0.862165 -0.297452 11.00000 -1.20000
AFIX 0
C00O 1 -0.030582 -0.961954 -0.350728 11.00000 0.04258 0.06208 =
0.10115 0.03045 0.01054 0.01087
AFIX 43
H00O 2 0.033435 -1.013633 -0.323592 11.00000 -1.20000
AFIX 0
HKLF 4
REM wtl-zlx-p1_a.res in P2(1)2(1)2(1)
REM R1 = 0.0726 for 2935 Fo > 4sig(Fo) and 0.0748 for all 3096 data
REM 217 parameters refined using 0 restraints
END
WGHT 0.1206 0.0000
REM Highest difference peak 0.333, deepest hole -0.628, 1-sigma level 0.162
Q1 1 -0.0810 -0.2174 -0.7567 11.00000 0.05 0.33
Q2 1 0.0545 -0.2485 -0.6622 11.00000 0.05 0.33
Q3 1 -0.4222 -0.3182 -0.3385 11.00000 0.05 0.32
Q4 1 -0.7724 -0.3948 -0.2526 11.00000 0.05 0.32
Q5 1 -0.4434 -0.8411 -0.2881 11.00000 0.05 0.32
Q6 1 -0.3875 -0.2761 -0.3564 11.00000 0.05 0.32
Q7 1 -0.5197 -0.4801 -0.4546 11.00000 0.05 0.31
Q8 1 -0.5097 -0.6598 -0.5261 11.00000 0.05 0.31
Q9 1 -0.4078 -0.5091 -0.5269 11.00000 0.05 0.31
Q10 1 0.0040 -1.0618 -0.5238 11.00000 0.05 0.30
Q11 1 -0.0487 -1.0132 -0.2141 11.00000 0.05 0.30
Q12 1 0.0558 -0.6546 -0.3711 11.00000 0.05 0.30
Q13 1 -0.4914 -0.2256 -0.6411 11.00000 0.05 0.30
Q14 1 -0.0265 -1.0390 -0.2034 11.00000 0.05 0.30
Q15 1 -0.4325 -0.2084 -0.3664 11.00000 0.05 0.29
Q16 1 -0.5334 -0.7164 -0.4987 11.00000 0.05 0.29
Q17 1 -0.0057 -0.2948 -0.7056 11.00000 0.05 0.29
Q18 1 -0.0660 -1.2464 -0.4200 11.00000 0.05 0.28
Q19 1 -0.0613 -1.1955 -0.4849 11.00000 0.05 0.28
Q20 1 -0.5540 -0.1853 -0.5984 11.00000 0.05 0.28
;
_shelx_res_checksum 44806
_shelx_SHELXL_version_number 2014/7
_olex2_date_sample_data_collection 2019-06-03
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.606
_oxdiff_exptl_absorpt_empirical_full_min 0.776
#######################################################################
#
# 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_wtl-zlx-2
_database_code_depnum_ccdc_archive 'CCDC 2004466'
loop_
_audit_author_name
_audit_author_address
zlx
;zlx
China
;
_audit_update_record
;
2020-05-18 deposited with the CCDC. 2020-09-03 downloaded from the CCDC.
;
_audit_creation_date 2019-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C23 H19 N O2'
_chemical_formula_sum 'C23 H19 N O2'
_chemical_formula_weight 341.39
_chemical_absolute_configuration ad
_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 orthorhombic
_space_group_IT_number 19
_space_group_name_H-M_alt 'P 21 21 21'
_space_group_name_Hall 'P 2ac 2ab'
loop_
_space_group_symop_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'
_cell_length_a 8.4921(2)
_cell_length_b 13.5753(4)
_cell_length_c 15.0981(5)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 1740.54(9)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 3849
_cell_measurement_temperature 295.88(16)
_cell_measurement_theta_max 71.5490
_cell_measurement_theta_min 4.3440
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.658
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.63155
_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 1.303
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 720
_exptl_crystal_size_max 0.6
_exptl_crystal_size_mid 0.6
_exptl_crystal_size_min 0.3
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0416
_diffrn_reflns_av_unetI/netI 0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_number 7797
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full 67.684
_diffrn_reflns_theta_max 71.397
_diffrn_reflns_theta_min 4.380
_diffrn_ambient_environment air
_diffrn_ambient_temperature 295.88(16)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):
# Type Start End Width t~exp~ \w \q \k \f Frames
#--------------------------------------------------------------------------
1 \w -103.00 -19.00 1.00 1.00 -- -36.04 -57.00 -60.00 84
2 \w -89.00 -2.00 1.00 1.00 -- -36.04 125.00-180.00 87
3 \w -105.00 33.00 1.00 1.00 -- -36.04 0.00-180.00 138
4 \w 100.00 176.00 1.00 1.00 -- 106.21 111.00 0.00 76
5 \w 38.00 124.00 1.00 1.00 -- 106.21 -45.00 0.00 86
6 \w 37.00 109.00 1.00 1.00 -- 106.21 -94.00 -60.00 72
7 \w 38.00 124.00 1.00 1.00 -- 106.21 -45.00 -90.00 86
8 \w 88.00 173.00 1.00 1.00 -- 106.21 61.00 -30.00 85
9 \w 85.00 176.00 1.00 1.00 -- 106.21 30.00-120.00 91
10 \w 39.00 133.00 1.00 1.00 -- 106.21 -77.00 60.00 94
11 \w -103.00 -52.00 1.00 1.00 -- -36.04 -57.00 120.00 51
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 -0.1690366000
_diffrn_orient_matrix_UB_12 0.0152348000
_diffrn_orient_matrix_UB_13 -0.0345410000
_diffrn_orient_matrix_UB_21 -0.0656309000
_diffrn_orient_matrix_UB_22 -0.0271465000
_diffrn_orient_matrix_UB_23 0.0919853000
_diffrn_orient_matrix_UB_31 0.0070353000
_diffrn_orient_matrix_UB_32 0.1090494000
_diffrn_orient_matrix_UB_33 0.0276597000
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source 'fine-focus sealed X-ray tube'
_diffrn_source_type 'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage 0.718
_reflns_Friedel_fraction_full 0.999
_reflns_Friedel_fraction_max 0.966
_reflns_number_gt 3132
_reflns_number_total 3330
_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 > 2\s(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 0.391
_refine_diff_density_min -0.400
_refine_diff_density_rms 0.130
_refine_ls_abs_structure_details
;
Flack x determined using 1216 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack 0.0(2)
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.116
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 235
_refine_ls_number_reflns 3330
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0690
_refine_ls_R_factor_gt 0.0666
_refine_ls_restrained_S_all 1.116
_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/[\s^2^(Fo^2^)+(0.1149P)^2^+0.0107P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1623
_refine_ls_wR_factor_ref 0.1667
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
C00B(H00B)
2.b Secondary CH2 refined with riding coordinates:
C00H(H00D,H00E), C00N(H00F,H00H)
2.c Aromatic/amide H refined with riding coordinates:
N003(H003), C005(H005), C006(H006), C009(H009), C00A(H00A), C00C(H00C),
C00G(H00G), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00O(H00O),
C00P(H00P), C00Q(H00Q)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_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 0.5622(3) 0.18822(17) 0.31179(15) 0.0490(6) Uani 1 1 d . . . . .
O002 O 0.4197(3) 0.37666(18) 0.22682(18) 0.0564(7) Uani 1 1 d . . . . .
N003 N 0.8077(3) 0.29886(19) 0.38238(16) 0.0420(6) Uani 1 1 d . . . . .
H003 H 0.9039 0.3170 0.3893 0.050 Uiso 1 1 calc R . . . .
C004 C 0.7951(3) 0.4251(2) 0.26741(17) 0.0331(6) Uani 1 1 d . . . . .
C005 C 0.5628(4) 0.0850(2) 0.4363(2) 0.0388(6) Uani 1 1 d . . . . .
H005 H 0.4864 0.0465 0.4089 0.047 Uiso 1 1 calc R . . . .
C006 C 0.7219(3) 0.5112(2) 0.2422(2) 0.0388(6) Uani 1 1 d . . . . .
H006 H 0.6167 0.5212 0.2567 0.047 Uiso 1 1 calc R . . . .
C007 C 0.6249(3) 0.16557(19) 0.39289(18) 0.0319(6) Uani 1 1 d . . . . .
C008 C 0.7431(3) 0.2222(2) 0.43174(18) 0.0334(6) Uani 1 1 d . . . . .
C009 C 0.7939(4) 0.1973(2) 0.5159(2) 0.0418(7) Uani 1 1 d . . . . .
H009 H 0.8726 0.2344 0.5428 0.050 Uiso 1 1 calc R . . . .
C00A C 0.7292(4) 0.1179(2) 0.5608(2) 0.0474(8) Uani 1 1 d . . . . .
H00A H 0.7632 0.1029 0.6178 0.057 Uiso 1 1 calc R . . . .
C00B C 0.7039(3) 0.3472(2) 0.31801(17) 0.0341(6) Uani 1 1 d . . . . .
H00B H 0.6178 0.3794 0.3501 0.041 Uiso 1 1 calc R . . . .
C00C C 0.6149(4) 0.0615(2) 0.5211(2) 0.0464(8) Uani 1 1 d . . . . .
H00C H 0.5724 0.0078 0.5508 0.056 Uiso 1 1 calc R . . . .
C00D C 0.5178(4) 0.1529(2) 0.10904(19) 0.0414(7) Uani 1 1 d . . . . .
C00E C 0.4274(4) 0.2324(2) 0.13858(18) 0.0373(6) Uani 1 1 d . . . . .
C00F C 0.4858(3) 0.3009(2) 0.20760(18) 0.0345(6) Uani 1 1 d . . . . .
C00G C 0.8035(4) 0.5835(2) 0.1953(2) 0.0489(8) Uani 1 1 d . . . . .
H00G H 0.7525 0.6411 0.1781 0.059 Uiso 1 1 calc R . . . .
C00H C 0.7505(4) 0.2212(2) 0.1944(2) 0.0424(7) Uani 1 1 d . . . . .
H00D H 0.8431 0.1997 0.2266 0.051 Uiso 1 1 calc R . . . .
H00E H 0.7831 0.2710 0.1521 0.051 Uiso 1 1 calc R . . . .
C00I C 0.6338(3) 0.26557(19) 0.25848(17) 0.0321(6) Uani 1 1 d . . . . .
C00J C 0.9557(3) 0.4128(2) 0.2473(2) 0.0428(7) Uani 1 1 d . . . . .
H00J H 1.0083 0.3563 0.2658 0.051 Uiso 1 1 calc R . . . .
C00K C 0.9599(4) 0.5693(3) 0.1744(2) 0.0504(8) Uani 1 1 d . . . . .
H00K H 1.0143 0.6173 0.1429 0.060 Uiso 1 1 calc R . . . .
C00L C 1.0358(4) 0.4845(3) 0.2000(2) 0.0516(8) Uani 1 1 d . . . . .
H00L H 1.1412 0.4752 0.1856 0.062 Uiso 1 1 calc R . . . .
C00M C 0.2745(4) 0.2464(3) 0.1056(2) 0.0524(8) Uani 1 1 d . . . . .
H00M H 0.2143 0.2993 0.1252 0.063 Uiso 1 1 calc R . . . .
C00N C 0.6795(4) 0.1336(3) 0.1447(3) 0.0517(8) Uani 1 1 d . . . . .
H00F H 0.7484 0.1163 0.0958 0.062 Uiso 1 1 calc R . . . .
H00H H 0.6749 0.0775 0.1844 0.062 Uiso 1 1 calc R . . . .
C00O C 0.4524(5) 0.0909(3) 0.0449(2) 0.0574(9) Uani 1 1 d . . . . .
H00O H 0.5120 0.0385 0.0237 0.069 Uiso 1 1 calc R . . . .
C00P C 0.2136(5) 0.1813(3) 0.0439(3) 0.0667(11) Uani 1 1 d . . . . .
H00P H 0.1111 0.1893 0.0235 0.080 Uiso 1 1 calc R . . . .
C00Q C 0.3045(6) 0.1046(3) 0.0127(3) 0.0691(12) Uani 1 1 d . . . . .
H00Q H 0.2648 0.0623 -0.0304 0.083 Uiso 1 1 calc R . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O001 0.0589(14) 0.0507(13) 0.0375(10) 0.0136(10) -0.0176(10) -0.0244(11)
O002 0.0392(11) 0.0521(14) 0.0779(17) -0.0183(13) -0.0116(11) 0.0139(10)
N003 0.0416(13) 0.0438(14) 0.0407(13) 0.0061(11) -0.0130(11) -0.0143(11)
C004 0.0342(13) 0.0322(13) 0.0328(12) -0.0033(11) 0.0010(11) -0.0062(11)
C005 0.0393(14) 0.0309(14) 0.0462(16) 0.0034(12) -0.0036(13) 0.0007(11)
C006 0.0376(13) 0.0345(14) 0.0444(15) -0.0040(12) -0.0007(12) 0.0001(11)
C007 0.0312(12) 0.0306(13) 0.0340(13) 0.0002(10) -0.0017(10) 0.0026(10)
C008 0.0331(13) 0.0312(14) 0.0359(13) -0.0014(11) -0.0013(11) 0.0030(10)
C009 0.0438(15) 0.0437(17) 0.0380(14) -0.0029(12) -0.0109(12) 0.0004(13)
C00A 0.0557(18) 0.0475(18) 0.0390(15) 0.0104(13) -0.0100(14) 0.0041(14)
C00B 0.0339(12) 0.0364(14) 0.0320(12) -0.0021(11) -0.0008(10) -0.0018(11)
C00C 0.0488(17) 0.0406(17) 0.0497(17) 0.0145(14) -0.0031(14) 0.0025(14)
C00D 0.0529(17) 0.0372(15) 0.0340(13) 0.0002(12) -0.0031(13) -0.0033(13)
C00E 0.0418(15) 0.0370(15) 0.0332(13) 0.0054(12) -0.0047(11) -0.0029(12)
C00F 0.0300(12) 0.0364(13) 0.0371(14) -0.0007(11) -0.0013(11) 0.0010(11)
C00G 0.0577(18) 0.0343(15) 0.0549(18) 0.0025(14) -0.0078(16) -0.0058(14)
C00H 0.0376(14) 0.0388(16) 0.0508(17) -0.0069(13) -0.0050(13) 0.0097(12)
C00I 0.0345(13) 0.0295(13) 0.0323(12) 0.0025(10) -0.0033(10) -0.0034(10)
C00J 0.0350(14) 0.0396(16) 0.0539(17) -0.0013(13) -0.0003(13) -0.0008(12)
C00K 0.0554(18) 0.0457(18) 0.0501(17) 0.0047(15) -0.0007(15) -0.0237(15)
C00L 0.0373(14) 0.0568(19) 0.061(2) -0.0051(17) 0.0076(14) -0.0126(14)
C00M 0.0498(18) 0.058(2) 0.0495(17) 0.0006(16) -0.0175(15) 0.0024(16)
C00N 0.0518(18) 0.0403(17) 0.063(2) -0.0130(15) -0.0069(16) 0.0109(15)
C00O 0.075(3) 0.050(2) 0.0470(17) -0.0113(16) -0.0073(17) -0.0043(18)
C00P 0.062(2) 0.078(3) 0.060(2) 0.003(2) -0.0302(19) -0.008(2)
C00Q 0.089(3) 0.067(3) 0.051(2) -0.0094(18) -0.025(2) -0.016(2)
_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 1.370(3) . ?
O001 C00I 1.456(3) . ?
O002 C00F 1.208(4) . ?
N003 H003 0.8600 . ?
N003 C008 1.392(4) . ?
N003 C00B 1.467(4) . ?
C004 C006 1.378(4) . ?
C004 C00B 1.517(4) . ?
C004 C00J 1.407(4) . ?
C005 H005 0.9300 . ?
C005 C007 1.380(4) . ?
C005 C00C 1.391(4) . ?
C006 H006 0.9300 . ?
C006 C00G 1.395(5) . ?
C007 C008 1.394(4) . ?
C008 C009 1.384(4) . ?
C009 H009 0.9300 . ?
C009 C00A 1.386(5) . ?
C00A H00A 0.9300 . ?
C00A C00C 1.374(5) . ?
C00B H00B 0.9800 . ?
C00B C00I 1.546(4) . ?
C00C H00C 0.9300 . ?
C00D C00E 1.397(4) . ?
C00D C00N 1.498(5) . ?
C00D C00O 1.398(4) . ?
C00E C00F 1.482(4) . ?
C00E C00M 1.403(4) . ?
C00F C00I 1.549(4) . ?
C00G H00G 0.9300 . ?
C00G C00K 1.379(5) . ?
C00H H00D 0.9700 . ?
C00H H00E 0.9700 . ?
C00H C00I 1.510(4) . ?
C00H C00N 1.531(5) . ?
C00J H00J 0.9300 . ?
C00J C00L 1.385(5) . ?
C00K H00K 0.9300 . ?
C00K C00L 1.375(5) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00P 1.384(5) . ?
C00N H00F 0.9700 . ?
C00N H00H 0.9700 . ?
C00O H00O 0.9300 . ?
C00O C00Q 1.359(6) . ?
C00P H00P 0.9300 . ?
C00P C00Q 1.380(7) . ?
C00Q H00Q 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
C007 O001 C00I 119.6(2) . . ?
C008 N003 H003 121.5 . . ?
C008 N003 C00B 116.9(2) . . ?
C00B N003 H003 121.5 . . ?
C006 C004 C00B 120.0(2) . . ?
C006 C004 C00J 118.6(3) . . ?
C00J C004 C00B 121.4(3) . . ?
C007 C005 H005 120.1 . . ?
C007 C005 C00C 119.8(3) . . ?
C00C C005 H005 120.1 . . ?
C004 C006 H006 119.6 . . ?
C004 C006 C00G 120.9(3) . . ?
C00G C006 H006 119.6 . . ?
O001 C007 C005 117.0(2) . . ?
O001 C007 C008 122.2(3) . . ?
C005 C007 C008 120.9(3) . . ?
N003 C008 C007 118.1(2) . . ?
C009 C008 N003 123.4(3) . . ?
C009 C008 C007 118.5(3) . . ?
C008 C009 H009 119.5 . . ?
C008 C009 C00A 121.0(3) . . ?
C00A C009 H009 119.5 . . ?
C009 C00A H00A 120.0 . . ?
C00C C00A C009 120.0(3) . . ?
C00C C00A H00A 120.0 . . ?
N003 C00B C004 109.8(2) . . ?
N003 C00B H00B 108.6 . . ?
N003 C00B C00I 107.2(2) . . ?
C004 C00B H00B 108.6 . . ?
C004 C00B C00I 113.8(2) . . ?
C00I C00B H00B 108.6 . . ?
C005 C00C H00C 120.0 . . ?
C00A C00C C005 119.9(3) . . ?
C00A C00C H00C 120.0 . . ?
C00E C00D C00N 121.6(3) . . ?
C00E C00D C00O 117.9(3) . . ?
C00O C00D C00N 120.5(3) . . ?
C00D C00E C00F 121.7(3) . . ?
C00D C00E C00M 120.0(3) . . ?
C00M C00E C00F 118.3(3) . . ?
O002 C00F C00E 123.2(3) . . ?
O002 C00F C00I 121.5(3) . . ?
C00E C00F C00I 115.2(2) . . ?
C006 C00G H00G 120.1 . . ?
C00K C00G C006 119.7(3) . . ?
C00K C00G H00G 120.1 . . ?
H00D C00H H00E 108.0 . . ?
C00I C00H H00D 109.3 . . ?
C00I C00H H00E 109.3 . . ?
C00I C00H C00N 111.4(3) . . ?
C00N C00H H00D 109.3 . . ?
C00N C00H H00E 109.3 . . ?
O001 C00I C00B 110.9(2) . . ?
O001 C00I C00F 99.1(2) . . ?
O001 C00I C00H 109.9(2) . . ?
C00B C00I C00F 112.3(2) . . ?
C00H C00I C00B 113.9(2) . . ?
C00H C00I C00F 109.8(2) . . ?
C004 C00J H00J 119.9 . . ?
C00L C00J C004 120.3(3) . . ?
C00L C00J H00J 119.9 . . ?
C00G C00K H00K 119.8 . . ?
C00L C00K C00G 120.3(3) . . ?
C00L C00K H00K 119.8 . . ?
C00J C00L H00L 119.9 . . ?
C00K C00L C00J 120.2(3) . . ?
C00K C00L H00L 119.9 . . ?
C00E C00M H00M 120.1 . . ?
C00P C00M C00E 119.8(4) . . ?
C00P C00M H00M 120.1 . . ?
C00D C00N C00H 113.7(3) . . ?
C00D C00N H00F 108.8 . . ?
C00D C00N H00H 108.8 . . ?
C00H C00N H00F 108.8 . . ?
C00H C00N H00H 108.8 . . ?
H00F C00N H00H 107.7 . . ?
C00D C00O H00O 118.9 . . ?
C00Q C00O C00D 122.2(4) . . ?
C00Q C00O H00O 118.9 . . ?
C00M C00P H00P 119.9 . . ?
C00M C00P C00Q 120.2(4) . . ?
C00Q C00P H00P 119.9 . . ?
C00O C00Q C00P 119.8(4) . . ?
C00O C00Q H00Q 120.1 . . ?
C00P C00Q H00Q 120.1 . . ?
_shelx_res_file
;
wtl-zlx-2.res created by SHELXL-2014/7
TITL wtl-zlx-2_a.res in P2(1)2(1)2(1)
REM Old TITL wtl-zlx-2 in P212121 #19
REM SHELXT solution in P2(1)2(1)2(1)
REM R1 0.145, Rweak 0.045, Alpha 0.008, Orientation as input
REM Flack x = -0.055 ( 0.280 ) from Parsons' quotients
REM Formula found by SHELXT: C23 N O2
CELL 1.54184 8.492052 13.575288 15.098138 90 90 90
ZERR 4 0.000249 0.000437 0.000481 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H N O
UNIT 92 76 4 8
L.S. 10
PLAN 20
BOND $H
LIST 6
fmap 2
ACTA
REM
REM
REM
WGHT 0.114900 0.010700
FVAR 10.58295
O001 4 0.562168 0.188218 0.311791 11.00000 0.05891 0.05070 =
0.03746 0.01356 -0.01762 -0.02438
O002 4 0.419668 0.376661 0.226819 11.00000 0.03919 0.05209 =
0.07791 -0.01827 -0.01163 0.01392
N003 3 0.807650 0.298860 0.382382 11.00000 0.04160 0.04378 =
0.04074 0.00612 -0.01300 -0.01433
AFIX 43
H003 2 0.903886 0.317016 0.389318 11.00000 -1.20000
AFIX 0
C004 1 0.795136 0.425074 0.267412 11.00000 0.03423 0.03224 =
0.03283 -0.00334 0.00095 -0.00618
C005 1 0.562790 0.084972 0.436273 11.00000 0.03934 0.03086 =
0.04618 0.00335 -0.00363 0.00069
AFIX 43
H005 2 0.486390 0.046452 0.408923 11.00000 -1.20000
AFIX 0
C006 1 0.721915 0.511175 0.242206 11.00000 0.03757 0.03448 =
0.04436 -0.00403 -0.00071 0.00012
AFIX 43
H006 2 0.616687 0.521224 0.256681 11.00000 -1.20000
AFIX 0
C007 1 0.624888 0.165569 0.392892 11.00000 0.03120 0.03055 =
0.03395 0.00022 -0.00174 0.00257
C008 1 0.743106 0.222201 0.431738 11.00000 0.03307 0.03124 =
0.03588 -0.00138 -0.00126 0.00299
C009 1 0.793933 0.197341 0.515930 11.00000 0.04378 0.04366 =
0.03805 -0.00285 -0.01092 0.00042
AFIX 43
H009 2 0.872638 0.234437 0.542800 11.00000 -1.20000
AFIX 0
C00A 1 0.729225 0.117945 0.560789 11.00000 0.05575 0.04749 =
0.03902 0.01040 -0.01004 0.00414
AFIX 43
H00A 2 0.763201 0.102861 0.617754 11.00000 -1.20000
AFIX 0
C00B 1 0.703913 0.347217 0.318010 11.00000 0.03386 0.03640 =
0.03195 -0.00209 -0.00076 -0.00184
AFIX 13
H00B 2 0.617817 0.379389 0.350125 11.00000 -1.20000
AFIX 0
C00C 1 0.614865 0.061527 0.521074 11.00000 0.04883 0.04064 =
0.04972 0.01453 -0.00309 0.00249
AFIX 43
H00C 2 0.572358 0.007765 0.550837 11.00000 -1.20000
AFIX 0
C00D 1 0.517771 0.152921 0.109038 11.00000 0.05295 0.03715 =
0.03403 0.00020 -0.00314 -0.00326
C00E 1 0.427412 0.232388 0.138578 11.00000 0.04179 0.03698 =
0.03319 0.00538 -0.00475 -0.00290
C00F 1 0.485806 0.300874 0.207600 11.00000 0.03004 0.03638 =
0.03707 -0.00075 -0.00128 0.00100
C00G 1 0.803466 0.583485 0.195269 11.00000 0.05765 0.03429 =
0.05485 0.00248 -0.00783 -0.00576
AFIX 43
H00G 2 0.752542 0.641051 0.178102 11.00000 -1.20000
AFIX 0
C00H 1 0.750495 0.221216 0.194396 11.00000 0.03755 0.03877 =
0.05083 -0.00691 -0.00500 0.00970
AFIX 23
H00D 2 0.843114 0.199660 0.226616 11.00000 -1.20000
H00E 2 0.783111 0.271000 0.152119 11.00000 -1.20000
AFIX 0
C00I 1 0.633777 0.265570 0.258475 11.00000 0.03450 0.02946 =
0.03233 0.00249 -0.00328 -0.00342
C00J 1 0.955693 0.412774 0.247283 11.00000 0.03495 0.03965 =
0.05394 -0.00135 -0.00028 -0.00084
AFIX 43
H00J 2 1.008250 0.356301 0.265776 11.00000 -1.20000
AFIX 0
C00K 1 0.959912 0.569259 0.174428 11.00000 0.05536 0.04568 =
0.05008 0.00474 -0.00073 -0.02366
AFIX 43
H00K 2 1.014347 0.617265 0.142906 11.00000 -1.20000
AFIX 0
C00L 1 1.035807 0.484470 0.200016 11.00000 0.03734 0.05683 =
0.06067 -0.00512 0.00757 -0.01261
AFIX 43
H00L 2 1.141227 0.475207 0.185560 11.00000 -1.20000
AFIX 0
C00M 1 0.274527 0.246415 0.105632 11.00000 0.04977 0.05789 =
0.04946 0.00056 -0.01745 0.00243
AFIX 43
H00M 2 0.214278 0.299324 0.125196 11.00000 -1.20000
AFIX 0
C00N 1 0.679461 0.133596 0.144661 11.00000 0.05176 0.04029 =
0.06307 -0.01298 -0.00688 0.01087
AFIX 23
H00F 2 0.748399 0.116323 0.095846 11.00000 -1.20000
H00H 2 0.674892 0.077493 0.184365 11.00000 -1.20000
AFIX 0
C00O 1 0.452370 0.090870 0.044942 11.00000 0.07483 0.05031 =
0.04702 -0.01128 -0.00726 -0.00427
AFIX 43
H00O 2 0.511971 0.038491 0.023674 11.00000 -1.20000
AFIX 0
C00P 1 0.213610 0.181309 0.043944 11.00000 0.06230 0.07786 =
0.06010 0.00288 -0.03019 -0.00780
AFIX 43
H00P 2 0.111093 0.189309 0.023507 11.00000 -1.20000
AFIX 0
C00Q 1 0.304544 0.104569 0.012680 11.00000 0.08910 0.06734 =
0.05094 -0.00939 -0.02538 -0.01597
AFIX 43
H00Q 2 0.264788 0.062331 -0.030353 11.00000 -1.20000
AFIX 0
HKLF 4
REM wtl-zlx-2_a.res in P2(1)2(1)2(1)
REM R1 = 0.0666 for 3132 Fo > 4sig(Fo) and 0.0690 for all 3330 data
REM 235 parameters refined using 0 restraints
END
WGHT 0.1145 0.0305
REM Highest difference peak 0.391, deepest hole -0.400, 1-sigma level 0.130
Q1 1 0.6172 0.3780 0.4738 11.00000 0.05 0.39
Q2 1 0.8622 0.3582 0.4250 11.00000 0.05 0.34
Q3 1 0.7960 0.1352 0.0002 11.00000 0.05 0.34
Q4 1 0.6424 0.5361 0.3304 11.00000 0.05 0.32
Q5 1 0.7487 0.3850 0.4778 11.00000 0.05 0.32
Q6 1 0.8316 0.0994 -0.0299 11.00000 0.05 0.32
Q7 1 0.1900 0.3959 0.0343 11.00000 0.05 0.31
Q8 1 1.0157 0.2472 0.2542 11.00000 0.05 0.31
Q9 1 -0.0252 0.1169 -0.0412 11.00000 0.05 0.28
Q10 1 0.6642 0.1174 0.6677 11.00000 0.05 0.25
Q11 1 0.8512 0.4462 0.4209 11.00000 0.05 0.25
Q12 1 0.8299 0.2856 0.5369 11.00000 0.05 0.25
Q13 1 0.6108 0.0250 0.2777 11.00000 0.05 0.24
Q14 1 1.2597 0.4556 0.0757 11.00000 0.05 0.24
Q15 1 1.1540 0.3190 0.2778 11.00000 0.05 0.24
Q16 1 0.0659 0.1551 -0.0795 11.00000 0.05 0.24
Q17 1 0.1033 0.1962 0.1894 11.00000 0.05 0.24
Q18 1 1.2770 0.5406 0.1557 11.00000 0.05 0.24
Q19 1 0.5930 0.5078 0.2757 11.00000 0.05 0.23
Q20 1 0.3330 0.0454 0.4597 11.00000 0.05 0.22
;
_shelx_res_checksum 38765
_shelx_SHELXL_version_number 2014/7
_olex2_date_sample_data_collection 2019-09-11
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.456
_oxdiff_exptl_absorpt_empirical_full_min 0.602