# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_ecv1_93_a
_database_code_depnum_ccdc_archive 'CCDC 2003343'
loop_
_audit_author_name
_audit_author_address
'Mark D. Smith'
;university of south carolina
United States of America
;
_audit_update_record
;
2020-05-11 deposited with the CCDC. 2020-07-02 downloaded from the CCDC.
;
_audit_creation_date 2016-12-01
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C15 H13 N O3'
_chemical_formula_sum 'C15 H13 N O3'
_chemical_formula_weight 255.26
_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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/n 1'
_space_group_name_Hall '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 10.7032(5)
_cell_length_b 6.6627(3)
_cell_length_c 16.9382(8)
_cell_angle_alpha 90
_cell_angle_beta 92.303(2)
_cell_angle_gamma 90
_cell_volume 1206.92(10)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 9106
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 30.030
_cell_measurement_theta_min 2.407
_shelx_estimated_absorpt_T_max 0.981
_shelx_estimated_absorpt_T_min 0.950
_exptl_absorpt_coefficient_mu 0.099
_exptl_absorpt_correction_T_max 0.7447
_exptl_absorpt_correction_T_min 0.7240
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1229 before and 0.0601 after correction.
The Ratio of minimum to maximum transmission is 0.9722.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.405
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description needle
_exptl_crystal_F_000 536
_exptl_crystal_size_max 0.52
_exptl_crystal_size_mid 0.26
_exptl_crystal_size_min 0.2
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0454
_diffrn_reflns_av_unetI/netI 0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_l_max 23
_diffrn_reflns_limit_l_min -23
_diffrn_reflns_number 56388
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full 30.180
_diffrn_reflns_theta_max 30.180
_diffrn_reflns_theta_min 2.211
_diffrn_ambient_temperature 100(2)
_diffrn_detector 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type 'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device 'three-circle diffractometer'
_diffrn_measurement_device_type 'Bruker D8 QUEST'
_diffrn_measurement_method '\w and \f scans'
_diffrn_radiation_monochromator 'mirror optics'
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'microfocus sealed X-ray tube'
_diffrn_source_type 'Incoatec I\ms'
_diffrn_special_details ?
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2970
_reflns_number_total 3575
_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 'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection 'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction 'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution 'XT (Sheldrick, 2015)'
_refine_diff_density_max 0.388
_refine_diff_density_min -0.214
_refine_diff_density_rms 0.047
_refine_ls_extinction_coef 0.015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method 'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref 1.046
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 191
_refine_ls_number_reflns 3575
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0525
_refine_ls_R_factor_gt 0.0401
_refine_ls_restrained_S_all 1.046
_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^)+(0.0437P)^2^+0.5302P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0967
_refine_ls_wR_factor_ref 0.1027
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
2. Shared sites
{C10A, C10B}
{C11A, C15B}
{C12A, C14B}
{C13A, C13B}
{C14A, C12B}
{C15A, C11B}
3. Restrained distances
O3A-H3A \\sim O3B-H3B
with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C10A) = Uanis(C10B)
Uanis(C11A) = Uanis(C15B)
Uanis(C12A) = Uanis(C14B)
Uanis(C13A) = Uanis(C13B)
Uanis(C14A) = Uanis(C12B)
Uanis(C15A) = Uanis(C11B)
5. Others
Sof(O3B)=Sof(H3B)=Sof(C10B)=Sof(C11B)=Sof(C12B)=Sof(H12B)=Sof(C13B)=Sof(H13B)=
Sof(C14B)=Sof(H14B)=Sof(C15B)=Sof(H15B)=1-FVAR(1)
Sof(O3A)=Sof(H3A)=Sof(C10A)=Sof(C11A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(H13A)=
Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
C2(H2), C3(H3), C6(H6), C7(H7)
6.b Secondary CH2 refined with riding coordinates:
C1(H1A,H1B)
6.c Aromatic/amide H refined with riding coordinates:
C8(H8), C9(H9), C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A), C12B(H12B),
C13B(H13B), C14B(H14B), C15B(H15B)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.48407(8) 0.79289(12) 0.10722(5) 0.02226(19) Uani 1 1 d . . . . .
O2 O 0.78191(8) 0.37964(14) 0.21693(5) 0.0249(2) Uani 1 1 d . . . . .
N1 N 0.61400(8) 0.56729(13) 0.17245(5) 0.01454(18) Uani 1 1 d . . . . .
C1 C 0.87514(11) 0.77789(18) 0.00799(7) 0.0223(2) Uani 1 1 d . . . . .
H1A H 0.909888 0.755616 -0.044592 0.027 Uiso 1 1 calc R . . . .
H1B H 0.915071 0.896027 0.033923 0.027 Uiso 1 1 calc R . . . .
C2 C 0.73087(11) 0.78915(18) 0.00501(6) 0.0201(2) Uani 1 1 d . . . . .
H2 H 0.692287 0.895257 -0.029885 0.024 Uiso 1 1 calc R . . . .
C3 C 0.71083(10) 0.81171(16) 0.09576(6) 0.0165(2) Uani 1 1 d . . . . .
H3 H 0.724034 0.953767 0.113232 0.020 Uiso 1 1 calc R . . . .
C4 C 0.58845(10) 0.73163(15) 0.12342(6) 0.0156(2) Uani 1 1 d . . . . .
C5 C 0.74062(10) 0.52143(17) 0.17918(6) 0.0163(2) Uani 1 1 d . . . . .
C6 C 0.81179(9) 0.67302(16) 0.13323(6) 0.0160(2) Uani 1 1 d . . . . .
H6 H 0.870854 0.750464 0.168893 0.019 Uiso 1 1 calc R . . . .
C7 C 0.88050(11) 0.58857(18) 0.06046(6) 0.0199(2) Uani 1 1 d . . . . .
H7 H 0.965345 0.529896 0.071725 0.024 Uiso 1 1 calc R . . . .
C8 C 0.78767(12) 0.45632(18) 0.01553(6) 0.0234(2) Uani 1 1 d . . . . .
H8 H 0.791909 0.314366 0.011106 0.028 Uiso 1 1 calc R . . . .
C9 C 0.69900(12) 0.57354(19) -0.01673(6) 0.0234(2) Uani 1 1 d . . . . .
H9 H 0.628277 0.530115 -0.047854 0.028 Uiso 1 1 calc R . . . .
O3A O 0.49847(12) 0.70468(18) 0.31354(7) 0.0226(3) Uani 0.685(3) 1 d D . P A 1
H3A H 0.566(2) 0.751(4) 0.2958(15) 0.037(7) Uiso 0.685(3) 1 d D . P A 1
C10A C 0.52092(9) 0.45400(16) 0.21146(6) 0.0145(2) Uani 0.685(3) 1 d . . P A 1
C11A C 0.46902(10) 0.52968(17) 0.27967(6) 0.0177(2) Uani 0.685(3) 1 d . . P A 1
C12A C 0.38214(10) 0.41338(19) 0.31827(6) 0.0211(2) Uani 0.685(3) 1 d . . P A 1
H12A H 0.345229 0.463785 0.364335 0.025 Uiso 0.685(3) 1 calc R . P A 1
C13A C 0.34923(10) 0.22508(19) 0.29002(7) 0.0223(2) Uani 0.685(3) 1 d . . P A 1
H13A H 0.289960 0.147114 0.316887 0.027 Uiso 0.685(3) 1 calc R . P A 1
C14A C 0.40211(10) 0.14908(18) 0.22271(7) 0.0209(2) Uani 0.685(3) 1 d . . P A 1
H14A H 0.379882 0.019149 0.203802 0.025 Uiso 0.685(3) 1 calc R . P A 1
C15A C 0.48779(10) 0.26467(17) 0.18327(6) 0.0167(2) Uani 0.685(3) 1 d . . P A 1
H15A H 0.523823 0.214179 0.136920 0.020 Uiso 0.685(3) 1 calc R . P A 1
O3B O 0.5348(2) 0.2044(4) 0.11611(14) 0.0188(7) Uani 0.315(3) 1 d D . P A 2
H3B H 0.508(6) 0.086(6) 0.105(4) 0.06(2) Uiso 0.315(3) 1 d D . P A 2
C10B C 0.52092(9) 0.45400(16) 0.21146(6) 0.0145(2) Uani 0.315(3) 1 d . . P A 2
C11B C 0.48779(10) 0.26467(17) 0.18327(6) 0.0167(2) Uani 0.315(3) 1 d . . P A 2
C12B C 0.40211(10) 0.14908(18) 0.22271(7) 0.0209(2) Uani 0.315(3) 1 d . . P A 2
H12B H 0.379882 0.019149 0.203802 0.025 Uiso 0.315(3) 1 calc R . P A 2
C13B C 0.34923(10) 0.22508(19) 0.29002(7) 0.0223(2) Uani 0.315(3) 1 d . . P A 2
H13B H 0.289960 0.147114 0.316887 0.027 Uiso 0.315(3) 1 calc R . P A 2
C14B C 0.38214(10) 0.41338(19) 0.31827(6) 0.0211(2) Uani 0.315(3) 1 d . . P A 2
H14B H 0.345229 0.463785 0.364335 0.025 Uiso 0.315(3) 1 calc R . P A 2
C15B C 0.46902(10) 0.52968(17) 0.27967(6) 0.0177(2) Uani 0.315(3) 1 d . . P A 2
H15B H 0.492528 0.658271 0.299419 0.021 Uiso 0.315(3) 1 calc R . P A 2
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
O1 0.0192(4) 0.0199(4) 0.0278(4) 0.0024(3) 0.0028(3) 0.0043(3)
O2 0.0185(4) 0.0323(5) 0.0241(4) 0.0125(4) 0.0038(3) 0.0047(3)
N1 0.0140(4) 0.0156(4) 0.0141(4) 0.0000(3) 0.0024(3) -0.0004(3)
C1 0.0243(6) 0.0244(6) 0.0189(5) 0.0035(4) 0.0080(4) -0.0006(4)
C2 0.0236(5) 0.0219(5) 0.0149(5) 0.0040(4) 0.0032(4) 0.0001(4)
C3 0.0192(5) 0.0142(5) 0.0162(5) -0.0007(4) 0.0040(4) -0.0014(4)
C4 0.0189(5) 0.0126(4) 0.0155(5) -0.0033(4) 0.0027(4) 0.0001(4)
C5 0.0155(5) 0.0217(5) 0.0119(4) 0.0006(4) 0.0022(3) -0.0007(4)
C6 0.0151(5) 0.0202(5) 0.0127(4) 0.0000(4) 0.0025(3) -0.0026(4)
C7 0.0212(5) 0.0228(5) 0.0163(5) 0.0024(4) 0.0069(4) 0.0025(4)
C8 0.0342(6) 0.0203(5) 0.0164(5) -0.0040(4) 0.0089(4) -0.0004(5)
C9 0.0302(6) 0.0280(6) 0.0122(5) -0.0030(4) 0.0022(4) -0.0042(5)
O3A 0.0248(7) 0.0202(6) 0.0236(6) -0.0078(5) 0.0117(5) -0.0067(5)
C10A 0.0127(4) 0.0170(5) 0.0138(4) 0.0018(4) 0.0018(3) -0.0006(4)
C11A 0.0154(5) 0.0211(5) 0.0166(5) -0.0030(4) 0.0018(4) 0.0001(4)
C12A 0.0159(5) 0.0307(6) 0.0170(5) 0.0005(4) 0.0047(4) 0.0009(4)
C13A 0.0150(5) 0.0281(6) 0.0240(5) 0.0060(5) 0.0030(4) -0.0028(4)
C14A 0.0179(5) 0.0200(5) 0.0248(5) 0.0016(4) 0.0001(4) -0.0037(4)
C15A 0.0152(5) 0.0190(5) 0.0158(5) -0.0007(4) 0.0010(4) 0.0003(4)
O3B 0.0214(13) 0.0164(13) 0.0191(13) -0.0036(9) 0.0063(9) -0.0007(10)
C10B 0.0127(4) 0.0170(5) 0.0138(4) 0.0018(4) 0.0018(3) -0.0006(4)
C11B 0.0152(5) 0.0190(5) 0.0158(5) -0.0007(4) 0.0010(4) 0.0003(4)
C12B 0.0179(5) 0.0200(5) 0.0248(5) 0.0016(4) 0.0001(4) -0.0037(4)
C13B 0.0150(5) 0.0281(6) 0.0240(5) 0.0060(5) 0.0030(4) -0.0028(4)
C14B 0.0159(5) 0.0307(6) 0.0170(5) 0.0005(4) 0.0047(4) 0.0009(4)
C15B 0.0154(5) 0.0211(5) 0.0166(5) -0.0030(4) 0.0018(4) 0.0001(4)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.2105(13) . ?
O2 C5 1.2140(14) . ?
N1 C4 1.3947(14) . ?
N1 C5 1.3894(13) . ?
N1 C10A 1.4323(13) . ?
N1 C10B 1.4323(13) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.5448(16) . ?
C1 C7 1.5428(16) . ?
C2 H2 1.0000 . ?
C2 C3 1.5679(15) . ?
C2 C9 1.5184(17) . ?
C3 H3 1.0000 . ?
C3 C4 1.5063(15) . ?
C3 C6 1.5393(15) . ?
C5 C6 1.5013(15) . ?
C6 H6 1.0000 . ?
C6 C7 1.5652(14) . ?
C7 H7 1.0000 . ?
C7 C8 1.5106(17) . ?
C8 H8 0.9500 . ?
C8 C9 1.3295(18) . ?
C9 H9 0.9500 . ?
O3A H3A 0.85(3) . ?
O3A C11A 1.3317(16) . ?
C10A C11A 1.3961(14) . ?
C10A C15A 1.3898(15) . ?
C11A C12A 1.3934(15) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.3833(17) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.3887(16) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.3892(15) . ?
C15A H15A 0.9500 . ?
O3B H3B 0.86(3) . ?
O3B C11B 1.324(3) . ?
C10B C11B 1.3898(15) . ?
C10B C15B 1.3961(14) . ?
C11B C12B 1.3892(15) . ?
C12B H12B 0.9500 . ?
C12B C13B 1.3887(16) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.3833(17) . ?
C14B H14B 0.9500 . ?
C14B C15B 1.3934(15) . ?
C15B H15B 0.9500 . ?
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 C10A 124.40(9) . . ?
C4 N1 C10B 124.40(9) . . ?
C5 N1 C4 112.88(8) . . ?
C5 N1 C10A 122.72(9) . . ?
C5 N1 C10B 122.72(9) . . ?
H1A C1 H1B 110.3 . . ?
C2 C1 H1A 112.9 . . ?
C2 C1 H1B 112.9 . . ?
C7 C1 H1A 112.9 . . ?
C7 C1 H1B 112.9 . . ?
C7 C1 C2 94.16(8) . . ?
C1 C2 H2 116.2 . . ?
C1 C2 C3 98.54(9) . . ?
C3 C2 H2 116.2 . . ?
C9 C2 C1 100.17(9) . . ?
C9 C2 H2 116.2 . . ?
C9 C2 C3 106.87(9) . . ?
C2 C3 H3 111.0 . . ?
C4 C3 C2 115.21(9) . . ?
C4 C3 H3 111.0 . . ?
C4 C3 C6 105.30(8) . . ?
C6 C3 C2 103.02(8) . . ?
C6 C3 H3 111.0 . . ?
O1 C4 N1 123.83(10) . . ?
O1 C4 C3 128.04(10) . . ?
N1 C4 C3 108.13(9) . . ?
O2 C5 N1 123.20(10) . . ?
O2 C5 C6 127.95(10) . . ?
N1 C5 C6 108.85(9) . . ?
C3 C6 H6 110.8 . . ?
C3 C6 C7 103.61(8) . . ?
C5 C6 C3 104.78(8) . . ?
C5 C6 H6 110.8 . . ?
C5 C6 C7 115.51(9) . . ?
C7 C6 H6 110.8 . . ?
C1 C7 C6 98.74(9) . . ?
C1 C7 H7 116.2 . . ?
C6 C7 H7 116.2 . . ?
C8 C7 C1 100.27(9) . . ?
C8 C7 C6 106.63(9) . . ?
C8 C7 H7 116.2 . . ?
C7 C8 H8 126.0 . . ?
C9 C8 C7 107.98(10) . . ?
C9 C8 H8 126.0 . . ?
C2 C9 H9 126.1 . . ?
C8 C9 C2 107.84(10) . . ?
C8 C9 H9 126.1 . . ?
C11A O3A H3A 110.8(17) . . ?
C11A C10A N1 119.91(9) . . ?
C15A C10A N1 119.50(9) . . ?
C15A C10A C11A 120.51(10) . . ?
O3A C11A C10A 125.28(11) . . ?
O3A C11A C12A 115.82(10) . . ?
C12A C11A C10A 118.86(10) . . ?
C11A C12A H12A 119.7 . . ?
C13A C12A C11A 120.50(10) . . ?
C13A C12A H12A 119.7 . . ?
C12A C13A H13A 119.7 . . ?
C12A C13A C14A 120.54(10) . . ?
C14A C13A H13A 119.7 . . ?
C13A C14A H14A 120.3 . . ?
C13A C14A C15A 119.44(11) . . ?
C15A C14A H14A 120.3 . . ?
C10A C15A H15A 119.9 . . ?
C14A C15A C10A 120.15(10) . . ?
C14A C15A H15A 119.9 . . ?
C11B O3B H3B 109(4) . . ?
C11B C10B N1 119.50(9) . . ?
C11B C10B C15B 120.51(10) . . ?
C15B C10B N1 119.91(9) . . ?
O3B C11B C10B 118.02(14) . . ?
O3B C11B C12B 121.72(15) . . ?
C12B C11B C10B 120.15(10) . . ?
C11B C12B H12B 120.3 . . ?
C13B C12B C11B 119.44(11) . . ?
C13B C12B H12B 120.3 . . ?
C12B C13B H13B 119.7 . . ?
C14B C13B C12B 120.54(10) . . ?
C14B C13B H13B 119.7 . . ?
C13B C14B H14B 119.7 . . ?
C13B C14B C15B 120.50(10) . . ?
C15B C14B H14B 119.7 . . ?
C10B C15B H15B 120.6 . . ?
C14B C15B C10B 118.86(10) . . ?
C14B C15B H15B 120.6 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3A H3A O2 0.85(3) 1.86(3) 2.6923(15) 165(2) 2_655
O3B H3B O1 0.86(3) 1.97(4) 2.798(3) 162(6) 1_545
_shelx_res_file
;
TITL ecv1_93_a_a.res in P2(1)/n
ecv1_93_a.res
created by SHELXL-2016/6 at 15:59:06 on 01-Dec-2016
REM Old TITL ECV1_93_A in P2/n
REM SHELXT solution in P2(1)/n
REM R1 0.139, Rweak 0.005, Alpha 0.021, Orientation as input
REM Formula found by SHELXT: C15 N O4
CELL 0.71073 10.7032 6.6627 16.9382 90 92.303 90
ZERR 4 0.0005 0.0003 0.0008 0 0.002 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 60 52 4 12
EQIV $1 1.5-X,0.5+Y,0.5-Z
EQIV $2 +X,-1+Y,+Z
SADI O3A H3A O3B H3B
EADP C10A C10B
EADP C11A C15B
EADP C12A C14B
EADP C13A C13B
EADP C14A C12B
EADP C15A C11B
EXYZ C10A C10B
EXYZ C11A C15B
EXYZ C12A C14B
EXYZ C13A C13B
EXYZ C14A C12B
EXYZ C15A C11B
L.S. 7
PLAN 9
SIZE 0.2 0.26 0.52
TEMP -173(2)
HTAB O3A O2_$1
HTAB O3B O1_$2
BOND $H
list 4
fmap 2
acta 60.36
REM
REM
REM
WGHT 0.043700 0.530200
EXTI 0.015139
FVAR 0.94856 0.68481
O1 4 0.484070 0.792888 0.107222 11.00000 0.01920 0.01988 =
0.02785 0.00244 0.00279 0.00429
O2 4 0.781908 0.379637 0.216931 11.00000 0.01845 0.03225 =
0.02408 0.01251 0.00378 0.00474
N1 3 0.614003 0.567285 0.172454 11.00000 0.01402 0.01560 =
0.01413 0.00003 0.00241 -0.00041
C1 1 0.875140 0.777890 0.007987 11.00000 0.02427 0.02442 =
0.01889 0.00346 0.00798 -0.00062
AFIX 23
H1A 2 0.909888 0.755616 -0.044592 11.00000 -1.20000
H1B 2 0.915071 0.896027 0.033923 11.00000 -1.20000
AFIX 0
C2 1 0.730868 0.789148 0.005006 11.00000 0.02362 0.02193 =
0.01491 0.00402 0.00324 0.00008
AFIX 13
H2 2 0.692287 0.895257 -0.029885 11.00000 -1.20000
AFIX 0
C3 1 0.710825 0.811712 0.095761 11.00000 0.01924 0.01418 =
0.01623 -0.00072 0.00402 -0.00142
AFIX 13
H3 2 0.724034 0.953767 0.113232 11.00000 -1.20000
AFIX 0
C4 1 0.588453 0.731626 0.123419 11.00000 0.01891 0.01259 =
0.01546 -0.00327 0.00273 0.00012
C5 1 0.740619 0.521429 0.179184 11.00000 0.01552 0.02168 =
0.01190 0.00059 0.00224 -0.00070
C6 1 0.811792 0.673022 0.133233 11.00000 0.01510 0.02024 =
0.01275 -0.00005 0.00254 -0.00256
AFIX 13
H6 2 0.870854 0.750464 0.168893 11.00000 -1.20000
AFIX 0
C7 1 0.880499 0.588567 0.060456 11.00000 0.02115 0.02282 =
0.01634 0.00239 0.00689 0.00253
AFIX 13
H7 2 0.965345 0.529896 0.071725 11.00000 -1.20000
AFIX 0
C8 1 0.787673 0.456322 0.015529 11.00000 0.03418 0.02027 =
0.01642 -0.00401 0.00893 -0.00038
AFIX 43
H8 2 0.791909 0.314366 0.011106 11.00000 -1.20000
AFIX 0
C9 1 0.699000 0.573538 -0.016733 11.00000 0.03016 0.02798 =
0.01223 -0.00301 0.00216 -0.00423
AFIX 43
H9 2 0.628277 0.530115 -0.047854 11.00000 -1.20000
AFIX 0
PART 1
O3A 4 0.498467 0.704678 0.313542 21.00000 0.02482 0.02019 =
0.02362 -0.00781 0.01175 -0.00666
H3A 2 0.565898 0.751122 0.295803 21.00000 0.03740
C10A 1 0.520923 0.453999 0.211459 21.00000 0.01269 0.01696 =
0.01382 0.00176 0.00176 -0.00064
C11A 1 0.469018 0.529684 0.279665 21.00000 0.01538 0.02113 =
0.01656 -0.00298 0.00183 0.00011
C12A 1 0.382139 0.413378 0.318268 21.00000 0.01587 0.03067 =
0.01703 0.00048 0.00465 0.00090
AFIX 43
H12A 2 0.345229 0.463785 0.364335 21.00000 -1.20000
AFIX 0
C13A 1 0.349226 0.225079 0.290021 21.00000 0.01499 0.02809 =
0.02404 0.00598 0.00295 -0.00283
AFIX 43
H13A 2 0.289960 0.147114 0.316887 21.00000 -1.20000
AFIX 0
C14A 1 0.402111 0.149081 0.222712 21.00000 0.01788 0.02001 =
0.02482 0.00163 0.00006 -0.00369
AFIX 43
H14A 2 0.379882 0.019149 0.203802 21.00000 -1.20000
AFIX 0
C15A 1 0.487794 0.264667 0.183268 21.00000 0.01521 0.01904 =
0.01578 -0.00070 0.00104 0.00030
AFIX 43
H15A 2 0.523823 0.214179 0.136920 21.00000 -1.20000
AFIX 0
PART 0
PART 2
O3B 4 0.534774 0.204414 0.116106 -21.00000 0.02143 0.01640 =
0.01914 -0.00364 0.00626 -0.00074
H3B 2 0.508365 0.085684 0.105217 -21.00000 0.06356
C10B 1 0.520923 0.453999 0.211459 -21.00000 0.01269 0.01696 =
0.01382 0.00176 0.00176 -0.00064
C11B 1 0.487794 0.264667 0.183268 -21.00000 0.01521 0.01904 =
0.01578 -0.00070 0.00104 0.00030
C12B 1 0.402111 0.149081 0.222712 -21.00000 0.01788 0.02001 =
0.02482 0.00163 0.00006 -0.00369
AFIX 43
H12B 2 0.379882 0.019149 0.203802 -21.00000 -1.20000
AFIX 0
C13B 1 0.349226 0.225079 0.290021 -21.00000 0.01499 0.02809 =
0.02404 0.00598 0.00295 -0.00283
AFIX 43
H13B 2 0.289960 0.147114 0.316887 -21.00000 -1.20000
AFIX 0
C14B 1 0.382139 0.413378 0.318268 -21.00000 0.01587 0.03067 =
0.01703 0.00048 0.00465 0.00090
AFIX 43
H14B 2 0.345229 0.463785 0.364335 -21.00000 -1.20000
AFIX 0
C15B 1 0.469018 0.529684 0.279665 -21.00000 0.01538 0.02113 =
0.01656 -0.00298 0.00183 0.00011
AFIX 43
H15B 2 0.492528 0.658271 0.299419 -21.00000 -1.20000
AFIX 0
HKLF 4
REM ecv1_93_a_a.res in P2(1)/n
REM R1 = 0.0401 for 2970 Fo > 4sig(Fo) and 0.0525 for all 3575 data
REM 191 parameters refined using 1 restraints
END
WGHT 0.0437 0.5299
REM Highest difference peak 0.388, deepest hole -0.214, 1-sigma level 0.047
Q1 1 0.7745 0.5914 0.1523 11.00000 0.05 0.39
Q2 1 0.6491 0.7891 0.1073 11.00000 0.05 0.35
Q3 1 0.4233 0.4800 0.2976 11.00000 0.05 0.32
Q4 1 0.5049 0.4785 0.2504 11.00000 0.05 0.31
Q5 1 0.7596 0.7401 0.1146 11.00000 0.05 0.30
Q6 1 0.3654 0.2039 0.2496 11.00000 0.05 0.30
Q7 1 0.8006 0.7796 0.0039 11.00000 0.05 0.29
Q8 1 0.5680 0.5186 0.1900 11.00000 0.05 0.29
Q9 1 0.7057 0.6827 -0.0040 11.00000 0.05 0.28
;
_shelx_res_checksum 20665
_shelx_SHELXL_version_number 2016/6
_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_ecv1_129
_database_code_depnum_ccdc_archive 'CCDC 2003347'
loop_
_audit_author_name
_audit_author_address
'Mark D. Smith'
;university of south carolina
United States of America
;
_audit_update_record
;
2020-05-11 deposited with the CCDC. 2020-07-02 downloaded from the CCDC.
;
_audit_creation_date 2017-12-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number 2017/1
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C17 H14 N2 O3'
_chemical_formula_sum 'C17 H14 N2 O3'
_chemical_formula_weight 294.30
_chemical_absolute_configuration unk
_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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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 25.6129(11)
_cell_length_b 7.2650(3)
_cell_length_c 7.5367(3)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 1402.41(10)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 9963
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 29.97
_cell_measurement_theta_min 2.91
_shelx_estimated_absorpt_T_max 0.990
_shelx_estimated_absorpt_T_min 0.966
_exptl_absorpt_coefficient_mu 0.097
_exptl_absorpt_correction_T_max 0.8622
_exptl_absorpt_correction_T_min 0.8419
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1245 before and 0.0436 after correction.
The Ratio of minimum to maximum transmission is 0.9765.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.394
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description plate
_exptl_crystal_F_000 616
_exptl_crystal_size_max 0.36
_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 0.0300
_diffrn_reflns_av_unetI/netI 0.0125
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max 36
_diffrn_reflns_limit_h_min -36
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_l_max 10
_diffrn_reflns_limit_l_min -10
_diffrn_reflns_number 73700
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full 30.080
_diffrn_reflns_theta_max 30.082
_diffrn_reflns_theta_min 2.914
_diffrn_ambient_temperature 100(2)
_diffrn_detector 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type 'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device 'three-circle diffractometer'
_diffrn_measurement_device_type 'Bruker D8 QUEST'
_diffrn_measurement_method '\w and \f scans'
_diffrn_radiation_monochromator 'mirror optics'
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'microfocus sealed X-ray tube'
_diffrn_source_type 'Incoatec I\ms'
_diffrn_special_details ?
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.865
_reflns_Friedel_fraction_full 0.996
_reflns_Friedel_fraction_max 0.995
_reflns_number_gt 3949
_reflns_number_total 4118
_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 'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection 'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction 'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution 'XT (Sheldrick, 2015)'
_refine_diff_density_max 0.279
_refine_diff_density_min -0.175
_refine_diff_density_rms 0.038
_refine_ls_abs_structure_details
;
Flack x determined using 1765 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack 0.11(13)
_refine_ls_extinction_coef 0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method 'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref 1.032
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 201
_refine_ls_number_reflns 4118
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0298
_refine_ls_R_factor_gt 0.0278
_refine_ls_restrained_S_all 1.032
_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^)+(0.0472P)^2^+0.2415P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0735
_refine_ls_wR_factor_ref 0.0748
_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 Ternary CH refined with riding coordinates:
C2(H2), C3(H3), C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
C8(H8), C9(H9), C12(H12), C13(H13), C15(H15)
2.d Idealised Me refined as rotating group:
C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.30497(4) 0.21168(15) 0.68149(13) 0.0180(2) Uani 1 1 d . . . . .
O2 O 0.39083(4) 0.64325(14) 0.35070(15) 0.0185(2) Uani 1 1 d . . . . .
O3 O 0.37283(4) 0.69992(13) 0.77487(14) 0.0160(2) Uani 1 1 d . . . . .
N1 N 0.35674(4) 0.42639(15) 0.54169(14) 0.0112(2) Uani 1 1 d . . . . .
N2 N 0.53251(6) -0.0334(2) 0.7693(2) 0.0304(3) Uani 1 1 d . . . . .
C1 C 0.26295(6) 0.2915(2) 0.09840(18) 0.0166(3) Uani 1 1 d . . . . .
H1A H 0.260567 0.209584 -0.006284 0.020 Uiso 1 1 calc R . . . .
H1B H 0.232383 0.374710 0.103224 0.020 Uiso 1 1 calc R . . . .
C2 C 0.27176(5) 0.18535(18) 0.27325(19) 0.0153(2) Uani 1 1 d . . . . .
H2 H 0.244629 0.091987 0.304972 0.018 Uiso 1 1 calc R . . . .
C3 C 0.27718(5) 0.35385(17) 0.40266(17) 0.0113(2) Uani 1 1 d . . . . .
H3 H 0.242248 0.400722 0.441036 0.014 Uiso 1 1 calc R . . . .
C4 C 0.31226(5) 0.31729(18) 0.55967(17) 0.0116(2) Uani 1 1 d . . . . .
C5 C 0.35620(5) 0.53835(17) 0.38979(18) 0.0118(2) Uani 1 1 d . . . . .
C6 C 0.30663(5) 0.49780(16) 0.28934(18) 0.0107(2) Uani 1 1 d . . . . .
H6 H 0.285270 0.611691 0.272440 0.013 Uiso 1 1 calc R . . . .
C7 C 0.31537(5) 0.39489(19) 0.10929(18) 0.0138(2) Uani 1 1 d . . . . .
H7 H 0.324319 0.474090 0.005116 0.017 Uiso 1 1 calc R . . . .
C8 C 0.35241(6) 0.23637(19) 0.14659(19) 0.0173(3) Uani 1 1 d . . . . .
H8 H 0.387617 0.227302 0.107953 0.021 Uiso 1 1 calc R . . . .
C9 C 0.32672(6) 0.11219(19) 0.24320(19) 0.0182(3) Uani 1 1 d . . . . .
H9 H 0.340264 -0.001333 0.285582 0.022 Uiso 1 1 calc R . . . .
C10 C 0.39965(5) 0.41686(18) 0.66138(17) 0.0115(2) Uani 1 1 d . . . . .
C11 C 0.40756(5) 0.56029(17) 0.78290(18) 0.0128(2) Uani 1 1 d . . . . .
C12 C 0.44913(5) 0.5492(2) 0.9024(2) 0.0176(3) Uani 1 1 d . . . . .
H12 H 0.454918 0.645457 0.985339 0.021 Uiso 1 1 calc R . . . .
C13 C 0.48196(5) 0.3972(2) 0.8997(2) 0.0182(3) Uani 1 1 d . . . . .
H13 H 0.510180 0.389641 0.981198 0.022 Uiso 1 1 calc R . . . .
C14 C 0.47370(5) 0.25562(19) 0.77792(19) 0.0152(2) Uani 1 1 d . . . . .
C15 C 0.43220(5) 0.26576(18) 0.65754(18) 0.0140(2) Uani 1 1 d . . . . .
H15 H 0.426529 0.169709 0.574210 0.017 Uiso 1 1 calc R . . . .
C16 C 0.38002(6) 0.8516(2) 0.8951(2) 0.0201(3) Uani 1 1 d . . . . .
H16A H 0.353892 0.946763 0.870445 0.030 Uiso 1 1 calc GR . . . .
H16B H 0.415078 0.903105 0.879388 0.030 Uiso 1 1 calc GR . . . .
H16C H 0.375983 0.808265 1.017510 0.030 Uiso 1 1 calc GR . . . .
C17 C 0.50723(5) 0.0963(2) 0.7749(2) 0.0205(3) Uani 1 1 d . . . . .
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
O1 0.0186(5) 0.0225(5) 0.0129(5) 0.0025(4) 0.0004(4) -0.0051(4)
O2 0.0165(4) 0.0199(5) 0.0191(5) 0.0044(4) -0.0026(4) -0.0065(4)
O3 0.0157(4) 0.0146(4) 0.0178(5) -0.0058(4) -0.0029(4) 0.0027(3)
N1 0.0110(5) 0.0123(5) 0.0104(5) -0.0006(4) -0.0010(4) -0.0008(4)
N2 0.0235(6) 0.0288(7) 0.0389(8) 0.0060(7) -0.0010(6) 0.0086(5)
C1 0.0191(6) 0.0186(6) 0.0121(6) -0.0009(5) -0.0037(5) -0.0041(5)
C2 0.0189(6) 0.0140(5) 0.0130(5) -0.0021(5) -0.0023(5) -0.0039(5)
C3 0.0097(5) 0.0128(5) 0.0113(5) -0.0021(4) -0.0003(4) -0.0007(4)
C4 0.0111(5) 0.0135(5) 0.0102(5) -0.0031(4) 0.0005(4) -0.0006(4)
C5 0.0126(5) 0.0108(5) 0.0121(5) -0.0011(4) -0.0006(4) 0.0010(4)
C6 0.0106(5) 0.0100(5) 0.0116(5) -0.0010(4) -0.0013(4) 0.0006(4)
C7 0.0152(6) 0.0159(6) 0.0102(5) -0.0014(4) -0.0004(4) 0.0009(5)
C8 0.0192(6) 0.0182(6) 0.0144(6) -0.0051(5) 0.0016(5) 0.0062(5)
C9 0.0267(7) 0.0121(6) 0.0159(6) -0.0046(5) -0.0023(5) 0.0050(5)
C10 0.0092(5) 0.0142(5) 0.0110(5) 0.0004(5) -0.0008(4) -0.0007(4)
C11 0.0109(5) 0.0142(5) 0.0132(5) -0.0008(5) 0.0004(5) -0.0007(4)
C12 0.0155(6) 0.0204(6) 0.0170(6) -0.0039(5) -0.0043(5) -0.0023(5)
C13 0.0116(5) 0.0244(7) 0.0186(6) 0.0021(6) -0.0041(5) -0.0014(5)
C14 0.0115(5) 0.0172(6) 0.0168(6) 0.0042(5) 0.0011(5) 0.0021(4)
C15 0.0139(6) 0.0149(5) 0.0133(5) -0.0002(5) 0.0014(5) 0.0004(4)
C16 0.0235(7) 0.0149(6) 0.0219(7) -0.0064(5) -0.0002(6) -0.0011(5)
C17 0.0148(6) 0.0230(6) 0.0237(7) 0.0044(6) -0.0004(5) 0.0023(5)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.2110(17) . ?
O2 C5 1.2059(16) . ?
O3 C11 1.3504(15) . ?
O3 C16 1.4387(17) . ?
N1 C4 1.3946(16) . ?
N1 C5 1.4044(17) . ?
N1 C10 1.4236(15) . ?
N2 C17 1.144(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.543(2) . ?
C1 C7 1.5406(19) . ?
C2 H2 1.0000 . ?
C2 C3 1.5713(18) . ?
C2 C9 1.522(2) . ?
C3 H3 1.0000 . ?
C3 C4 1.5093(18) . ?
C3 C6 1.5467(18) . ?
C5 C6 1.5074(17) . ?
C6 H6 1.0000 . ?
C6 C7 1.5654(19) . ?
C7 H7 1.0000 . ?
C7 C8 1.5183(19) . ?
C8 H8 0.9500 . ?
C8 C9 1.333(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.4020(17) . ?
C10 C15 1.3788(18) . ?
C11 C12 1.3968(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.3877(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.395(2) . ?
C14 C15 1.3994(19) . ?
C14 C17 1.4415(19) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O3 C16 117.57(11) . . ?
C4 N1 C5 113.60(10) . . ?
C4 N1 C10 122.79(11) . . ?
C5 N1 C10 123.53(10) . . ?
H1A C1 H1B 110.3 . . ?
C2 C1 H1A 112.9 . . ?
C2 C1 H1B 112.9 . . ?
C7 C1 H1A 112.9 . . ?
C7 C1 H1B 112.9 . . ?
C7 C1 C2 94.06(10) . . ?
C1 C2 H2 116.2 . . ?
C1 C2 C3 98.84(10) . . ?
C3 C2 H2 116.2 . . ?
C9 C2 C1 100.52(11) . . ?
C9 C2 H2 116.2 . . ?
C9 C2 C3 106.43(10) . . ?
C2 C3 H3 111.5 . . ?
C4 C3 C2 113.71(11) . . ?
C4 C3 H3 111.5 . . ?
C4 C3 C6 105.17(10) . . ?
C6 C3 C2 103.13(10) . . ?
C6 C3 H3 111.5 . . ?
O1 C4 N1 124.04(12) . . ?
O1 C4 C3 127.89(12) . . ?
N1 C4 C3 108.07(11) . . ?
O2 C5 N1 123.91(12) . . ?
O2 C5 C6 128.34(12) . . ?
N1 C5 C6 107.73(10) . . ?
C3 C6 H6 111.3 . . ?
C3 C6 C7 103.03(10) . . ?
C5 C6 C3 105.40(10) . . ?
C5 C6 H6 111.3 . . ?
C5 C6 C7 114.10(10) . . ?
C7 C6 H6 111.3 . . ?
C1 C7 C6 98.89(10) . . ?
C1 C7 H7 116.0 . . ?
C6 C7 H7 116.0 . . ?
C8 C7 C1 100.62(11) . . ?
C8 C7 C6 106.93(11) . . ?
C8 C7 H7 116.0 . . ?
C7 C8 H8 126.1 . . ?
C9 C8 C7 107.83(12) . . ?
C9 C8 H8 126.1 . . ?
C2 C9 H9 126.2 . . ?
C8 C9 C2 107.54(12) . . ?
C8 C9 H9 126.2 . . ?
C11 C10 N1 119.30(11) . . ?
C15 C10 N1 119.49(12) . . ?
C15 C10 C11 121.21(12) . . ?
O3 C11 C10 115.71(11) . . ?
O3 C11 C12 125.06(12) . . ?
C12 C11 C10 119.22(12) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.92(13) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.28(12) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 120.20(12) . . ?
C13 C14 C17 120.81(13) . . ?
C15 C14 C17 118.99(13) . . ?
C10 C15 C14 119.18(12) . . ?
C10 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 C14 177.59(18) . . ?
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
O2 C5 C6 C3 -179.72(13) . . . . ?
O2 C5 C6 C7 67.99(18) . . . . ?
O3 C11 C12 C13 179.12(13) . . . . ?
N1 C5 C6 C3 1.82(13) . . . . ?
N1 C5 C6 C7 -110.48(12) . . . . ?
N1 C10 C11 O3 -0.37(17) . . . . ?
N1 C10 C11 C12 178.86(12) . . . . ?
N1 C10 C15 C14 -178.75(12) . . . . ?
C1 C2 C3 C4 -149.88(11) . . . . ?
C1 C2 C3 C6 -36.56(12) . . . . ?
C1 C2 C9 C8 32.86(14) . . . . ?
C1 C7 C8 C9 -32.69(14) . . . . ?
C2 C1 C7 C6 -60.07(11) . . . . ?
C2 C1 C7 C8 49.14(12) . . . . ?
C2 C3 C4 O1 -66.89(17) . . . . ?
C2 C3 C4 N1 112.27(12) . . . . ?
C2 C3 C6 C5 -120.61(10) . . . . ?
C2 C3 C6 C7 -0.72(12) . . . . ?
C3 C2 C9 C8 -69.72(14) . . . . ?
C3 C6 C7 C1 37.84(11) . . . . ?
C3 C6 C7 C8 -66.20(12) . . . . ?
C4 N1 C5 O2 179.61(13) . . . . ?
C4 N1 C5 C6 -1.84(14) . . . . ?
C4 N1 C10 C11 -106.80(14) . . . . ?
C4 N1 C10 C15 72.25(16) . . . . ?
C4 C3 C6 C5 -1.20(13) . . . . ?
C4 C3 C6 C7 118.69(10) . . . . ?
C5 N1 C4 O1 -179.76(12) . . . . ?
C5 N1 C4 C3 1.04(14) . . . . ?
C5 N1 C10 C11 76.74(16) . . . . ?
C5 N1 C10 C15 -104.21(15) . . . . ?
C5 C6 C7 C1 151.55(11) . . . . ?
C5 C6 C7 C8 47.51(14) . . . . ?
C6 C3 C4 O1 -178.98(13) . . . . ?
C6 C3 C4 N1 0.18(13) . . . . ?
C6 C7 C8 C9 70.10(14) . . . . ?
C7 C1 C2 C3 59.46(11) . . . . ?
C7 C1 C2 C9 -49.20(12) . . . . ?
C7 C8 C9 C2 -0.15(16) . . . . ?
C9 C2 C3 C4 -46.08(14) . . . . ?
C9 C2 C3 C6 67.24(12) . . . . ?
C10 N1 C4 O1 3.5(2) . . . . ?
C10 N1 C4 C3 -175.75(11) . . . . ?
C10 N1 C5 O2 -3.6(2) . . . . ?
C10 N1 C5 C6 174.92(11) . . . . ?
C10 C11 C12 C13 0.0(2) . . . . ?
C11 C10 C15 C14 0.28(19) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C12 C13 C14 C17 -179.41(14) . . . . ?
C13 C14 C15 C10 -0.2(2) . . . . ?
C15 C10 C11 O3 -179.40(12) . . . . ?
C15 C10 C11 C12 -0.17(19) . . . . ?
C16 O3 C11 C10 -178.93(12) . . . . ?
C16 O3 C11 C12 1.89(19) . . . . ?
C17 C14 C15 C10 179.22(13) . . . . ?
_shelx_res_file
;
TITL ecv1_129_a.res in Pna2(1)
ecv1_129.res
created by SHELXL-2017/1 at 15:23:43 on 08-Dec-2017
REM Old TITL ECV1_129 in Pna2(1)
REM SHELXT solution in Pna2(1)
REM R1 0.082, Rweak 0.011, Alpha 0.001, Orientation as input
REM Flack x = 0.148 ( 0.130 ) from Parsons' quotients
REM Formula found by SHELXT: C17 N2 O3
CELL 0.71073 25.6129 7.265 7.5367 90 90 90
ZERR 4 0.0011 0.0003 0.0003 0 0 0
LATT -1
SYMM -X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,+Z
SYMM 0.5-X,0.5+Y,0.5+Z
SFAC C H N O
UNIT 68 56 8 12
L.S. 7
PLAN 9
SIZE 0.1 0.2 0.36
TEMP -173(2)
BOND $H
CONF
list 4
fmap 2
ACTA 60.16
REM
REM
REM
WGHT 0.047200 0.241500
EXTI 0.011034
FVAR 0.76252
O1 4 0.304971 0.211677 0.681490 11.00000 0.01860 0.02247 =
0.01285 0.00252 0.00037 -0.00510
O2 4 0.390827 0.643252 0.350704 11.00000 0.01650 0.01987 =
0.01912 0.00442 -0.00258 -0.00647
O3 4 0.372833 0.699917 0.774870 11.00000 0.01573 0.01461 =
0.01778 -0.00584 -0.00290 0.00267
N1 3 0.356741 0.426389 0.541686 11.00000 0.01099 0.01229 =
0.01036 -0.00065 -0.00101 -0.00076
N2 3 0.532512 -0.033424 0.769330 11.00000 0.02349 0.02884 =
0.03894 0.00604 -0.00097 0.00858
C1 1 0.262953 0.291471 0.098398 11.00000 0.01906 0.01865 =
0.01209 -0.00091 -0.00372 -0.00412
AFIX 23
H1A 2 0.260567 0.209584 -0.006284 11.00000 -1.20000
H1B 2 0.232383 0.374710 0.103224 11.00000 -1.20000
AFIX 0
C2 1 0.271757 0.185351 0.273254 11.00000 0.01885 0.01403 =
0.01302 -0.00212 -0.00230 -0.00394
AFIX 13
H2 2 0.244629 0.091987 0.304972 11.00000 -1.20000
AFIX 0
C3 1 0.277178 0.353850 0.402662 11.00000 0.00971 0.01278 =
0.01130 -0.00208 -0.00034 -0.00067
AFIX 13
H3 2 0.242248 0.400722 0.441036 11.00000 -1.20000
AFIX 0
C4 1 0.312257 0.317287 0.559674 11.00000 0.01108 0.01349 =
0.01017 -0.00306 0.00047 -0.00057
C5 1 0.356199 0.538354 0.389791 11.00000 0.01255 0.01083 =
0.01208 -0.00105 -0.00057 0.00097
C6 1 0.306627 0.497805 0.289335 11.00000 0.01057 0.00999 =
0.01160 -0.00103 -0.00133 0.00060
AFIX 13
H6 2 0.285270 0.611691 0.272440 11.00000 -1.20000
AFIX 0
C7 1 0.315368 0.394893 0.109287 11.00000 0.01520 0.01595 =
0.01022 -0.00140 -0.00045 0.00089
AFIX 13
H7 2 0.324319 0.474090 0.005116 11.00000 -1.20000
AFIX 0
C8 1 0.352405 0.236371 0.146589 11.00000 0.01923 0.01823 =
0.01444 -0.00514 0.00156 0.00619
AFIX 43
H8 2 0.387617 0.227302 0.107953 11.00000 -1.20000
AFIX 0
C9 1 0.326720 0.112186 0.243203 11.00000 0.02675 0.01208 =
0.01589 -0.00461 -0.00228 0.00501
AFIX 43
H9 2 0.340264 -0.001333 0.285582 11.00000 -1.20000
AFIX 0
C10 1 0.399653 0.416864 0.661378 11.00000 0.00921 0.01424 =
0.01095 0.00043 -0.00078 -0.00067
C11 1 0.407558 0.560293 0.782901 11.00000 0.01092 0.01416 =
0.01323 -0.00081 0.00045 -0.00074
C12 1 0.449128 0.549153 0.902372 11.00000 0.01547 0.02036 =
0.01699 -0.00388 -0.00431 -0.00234
AFIX 43
H12 2 0.454918 0.645457 0.985339 11.00000 -1.20000
AFIX 0
C13 1 0.481961 0.397232 0.899723 11.00000 0.01161 0.02442 =
0.01861 0.00215 -0.00406 -0.00138
AFIX 43
H13 2 0.510180 0.389641 0.981198 11.00000 -1.20000
AFIX 0
C14 1 0.473702 0.255618 0.777921 11.00000 0.01149 0.01717 =
0.01685 0.00424 0.00113 0.00212
C15 1 0.432203 0.265757 0.657545 11.00000 0.01388 0.01486 =
0.01332 -0.00024 0.00141 0.00042
AFIX 43
H15 2 0.426529 0.169709 0.574210 11.00000 -1.20000
AFIX 0
C16 1 0.380019 0.851603 0.895140 11.00000 0.02352 0.01494 =
0.02192 -0.00637 -0.00023 -0.00114
AFIX 137
H16A 2 0.353892 0.946763 0.870445 11.00000 -1.50000
H16B 2 0.415078 0.903105 0.879388 11.00000 -1.50000
H16C 2 0.375983 0.808265 1.017510 11.00000 -1.50000
AFIX 0
C17 1 0.507232 0.096283 0.774936 11.00000 0.01477 0.02297 =
0.02367 0.00442 -0.00037 0.00229
HKLF 4
REM ecv1_129_a.res in Pna2(1)
REM R1 = 0.0278 for 3949 Fo > 4sig(Fo) and 0.0298 for all 4118 data
REM 201 parameters refined using 1 restraints
END
WGHT 0.0472 0.2415
REM Highest difference peak 0.279, deepest hole -0.175, 1-sigma level 0.038
Q1 1 0.4305 0.5663 0.8336 11.00000 0.05 0.28
Q2 1 0.2935 0.3386 0.4859 11.00000 0.05 0.26
Q3 1 0.2890 0.3481 0.0917 11.00000 0.05 0.25
Q4 1 0.3310 0.5209 0.3314 11.00000 0.05 0.24
Q5 1 0.3104 0.4627 0.1933 11.00000 0.05 0.24
Q6 1 0.4023 0.4858 0.7322 11.00000 0.05 0.23
Q7 1 0.3355 0.3251 0.1319 11.00000 0.05 0.23
Q8 1 0.2906 0.4285 0.3426 11.00000 0.05 0.22
Q9 1 0.4608 0.2725 0.6981 11.00000 0.05 0.21
;
_shelx_res_checksum 41212
_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_ecv1_121
_database_code_depnum_ccdc_archive 'CCDC 2003344'
loop_
_audit_author_name
_audit_author_address
'Mark D. Smith'
;university of south carolina
United States of America
;
_audit_update_record
;
2020-05-11 deposited with the CCDC. 2020-07-02 downloaded from the CCDC.
;
_audit_creation_date 2017-11-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number 2017/1
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C16 H14 N2 O5'
_chemical_formula_sum 'C16 H14 N2 O5'
_chemical_formula_weight 314.29
_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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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 triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 7.7842(5)
_cell_length_b 9.7899(6)
_cell_length_c 10.0423(6)
_cell_angle_alpha 81.677(2)
_cell_angle_beta 82.193(2)
_cell_angle_gamma 67.584(2)
_cell_volume 697.29(8)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 9963
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 30.120
_cell_measurement_theta_min 2.262
_shelx_estimated_absorpt_T_max 0.960
_shelx_estimated_absorpt_T_min 0.941
_exptl_absorpt_coefficient_mu 0.113
_exptl_absorpt_correction_T_max 0.8622
_exptl_absorpt_correction_T_min 0.8072
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1276 before and 0.0597 after correction.
The Ratio of minimum to maximum transmission is 0.9362.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.497
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 328
_exptl_crystal_size_max 0.54
_exptl_crystal_size_mid 0.44
_exptl_crystal_size_min 0.36
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0480
_diffrn_reflns_av_unetI/netI 0.0333
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_number 31746
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full 30.190
_diffrn_reflns_theta_max 30.192
_diffrn_reflns_theta_min 2.262
_diffrn_ambient_temperature 100(2)
_diffrn_detector 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type 'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device 'three-circle diffractometer'
_diffrn_measurement_device_type 'Bruker D8 QUEST'
_diffrn_measurement_method '\w and \f scans'
_diffrn_radiation_monochromator 'mirror optics'
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'microfocus sealed X-ray tube'
_diffrn_source_type 'Incoatec I\ms'
_diffrn_special_details ?
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 3192
_reflns_number_total 4121
_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 'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection 'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction 'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution 'XT (Sheldrick, 2015)'
_refine_diff_density_max 0.384
_refine_diff_density_min -0.306
_refine_diff_density_rms 0.056
_refine_ls_extinction_coef 0.031(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method 'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref 1.029
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 210
_refine_ls_number_reflns 4121
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0645
_refine_ls_R_factor_gt 0.0440
_refine_ls_restrained_S_all 1.029
_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^)+(0.0461P)^2^+0.3803P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1003
_refine_ls_wR_factor_ref 0.1111
_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 Ternary CH refined with riding coordinates:
C2(H2), C3(H3), C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
C8(H8), C9(H9), C12(H12), C13(H13), C15(H15)
2.d Idealised Me refined as rotating group:
C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.94016(13) 0.18709(11) 0.49448(9) 0.0196(2) Uani 1 1 d . . . . .
O2 O 0.70453(13) 0.17786(10) 0.10386(9) 0.0193(2) Uani 1 1 d . . . . .
O3 O 0.60473(13) 0.47610(10) 0.21301(10) 0.0212(2) Uani 1 1 d . . . . .
O4 O 0.32587(15) 0.10105(12) 0.68322(11) 0.0290(3) Uani 1 1 d . . . . .
O5 O 0.10454(14) 0.31555(12) 0.70560(10) 0.0246(2) Uani 1 1 d . . . . .
N1 N 0.78183(14) 0.19288(11) 0.31407(10) 0.0139(2) Uani 1 1 d . . . . .
N2 N 0.25154(15) 0.23514(13) 0.64976(11) 0.0184(2) Uani 1 1 d . . . . .
C1 C 1.32198(18) 0.09525(16) 0.10656(13) 0.0195(3) Uani 1 1 d . . . . .
H1A H 1.382834 -0.014311 0.118896 0.023 Uiso 1 1 calc R . . . .
H1B H 1.408442 0.139299 0.053521 0.023 Uiso 1 1 calc R . . . .
C2 C 1.24015(18) 0.16322(16) 0.24021(14) 0.0191(3) Uani 1 1 d . . . . .
H2 H 1.332229 0.156110 0.303813 0.023 Uiso 1 1 calc R . . . .
C3 C 1.10780(17) 0.07542(14) 0.29001(12) 0.0153(2) Uani 1 1 d . . . . .
H3 H 1.178595 -0.026469 0.332202 0.018 Uiso 1 1 calc R . . . .
C4 C 0.94131(17) 0.15586(14) 0.38165(12) 0.0147(2) Uani 1 1 d . . . . .
C5 C 0.82107(17) 0.15044(13) 0.18163(12) 0.0148(2) Uani 1 1 d . . . . .
C6 C 1.02961(17) 0.06862(14) 0.15914(12) 0.0145(2) Uani 1 1 d . . . . .
H6 H 1.059915 -0.036478 0.141822 0.017 Uiso 1 1 calc R . . . .
C7 C 1.13207(18) 0.14800(15) 0.04761(13) 0.0174(3) Uani 1 1 d . . . . .
H7 H 1.134932 0.127634 -0.047579 0.021 Uiso 1 1 calc R . . . .
C8 C 1.05456(19) 0.30981(15) 0.07405(14) 0.0203(3) Uani 1 1 d . . . . .
H8 H 0.974914 0.390353 0.019314 0.024 Uiso 1 1 calc R . . . .
C9 C 1.11805(19) 0.31897(15) 0.18774(15) 0.0214(3) Uani 1 1 d . . . . .
H9 H 1.091648 0.407227 0.228705 0.026 Uiso 1 1 calc R . . . .
C10 C 0.60039(16) 0.27731(14) 0.37092(12) 0.0143(2) Uani 1 1 d . . . . .
C11 C 0.51030(17) 0.42561(14) 0.31849(13) 0.0157(2) Uani 1 1 d . . . . .
C12 C 0.33678(18) 0.51076(14) 0.37830(13) 0.0175(3) Uani 1 1 d . . . . .
H12 H 0.275052 0.610841 0.343117 0.021 Uiso 1 1 calc R . . . .
C13 C 0.25469(17) 0.44899(15) 0.48915(13) 0.0172(3) Uani 1 1 d . . . . .
H13 H 0.138329 0.507298 0.532019 0.021 Uiso 1 1 calc R . . . .
C14 C 0.34334(17) 0.30184(14) 0.53699(12) 0.0156(2) Uani 1 1 d . . . . .
C15 C 0.51648(17) 0.21460(14) 0.47925(12) 0.0148(2) Uani 1 1 d . . . . .
H15 H 0.575803 0.113875 0.513676 0.018 Uiso 1 1 calc R . . . .
C16 C 0.5078(2) 0.61784(17) 0.14253(17) 0.0313(4) Uani 1 1 d . . . . .
H16A H 0.478095 0.695818 0.202565 0.047 Uiso 1 1 calc GR . . . .
H16B H 0.392181 0.618271 0.113902 0.047 Uiso 1 1 calc GR . . . .
H16C H 0.587081 0.636252 0.062978 0.047 Uiso 1 1 calc GR . . . .
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
O1 0.0169(4) 0.0241(5) 0.0155(4) -0.0035(4) -0.0023(3) -0.0041(4)
O2 0.0181(5) 0.0217(5) 0.0194(4) -0.0003(4) -0.0061(4) -0.0080(4)
O3 0.0183(5) 0.0171(5) 0.0239(5) 0.0045(4) 0.0006(4) -0.0048(4)
O4 0.0241(5) 0.0217(5) 0.0316(6) 0.0059(4) 0.0049(4) -0.0031(4)
O5 0.0165(5) 0.0282(5) 0.0239(5) -0.0048(4) 0.0060(4) -0.0042(4)
N1 0.0107(5) 0.0145(5) 0.0153(5) -0.0013(4) -0.0014(4) -0.0033(4)
N2 0.0148(5) 0.0217(6) 0.0177(5) -0.0020(4) -0.0005(4) -0.0060(4)
C1 0.0146(6) 0.0238(7) 0.0204(6) -0.0061(5) 0.0027(5) -0.0074(5)
C2 0.0122(6) 0.0268(7) 0.0206(6) -0.0078(5) -0.0002(5) -0.0083(5)
C3 0.0118(5) 0.0176(6) 0.0145(5) -0.0018(4) -0.0017(4) -0.0031(5)
C4 0.0126(5) 0.0147(6) 0.0154(5) 0.0008(4) -0.0022(4) -0.0040(4)
C5 0.0156(6) 0.0133(5) 0.0159(6) 0.0001(4) -0.0012(4) -0.0064(5)
C6 0.0135(5) 0.0147(6) 0.0157(5) -0.0031(4) -0.0005(4) -0.0052(4)
C7 0.0171(6) 0.0206(6) 0.0155(6) -0.0028(5) 0.0013(5) -0.0087(5)
C8 0.0181(6) 0.0174(6) 0.0247(7) 0.0015(5) 0.0013(5) -0.0082(5)
C9 0.0189(6) 0.0195(6) 0.0291(7) -0.0089(5) 0.0065(5) -0.0112(5)
C10 0.0100(5) 0.0158(6) 0.0161(6) -0.0026(4) -0.0020(4) -0.0029(4)
C11 0.0134(6) 0.0173(6) 0.0166(6) 0.0000(4) -0.0026(4) -0.0062(5)
C12 0.0135(6) 0.0152(6) 0.0220(6) -0.0013(5) -0.0041(5) -0.0029(5)
C13 0.0115(6) 0.0197(6) 0.0197(6) -0.0049(5) -0.0022(5) -0.0037(5)
C14 0.0123(5) 0.0196(6) 0.0151(6) -0.0018(4) -0.0006(4) -0.0063(5)
C15 0.0131(6) 0.0146(6) 0.0161(6) -0.0013(4) -0.0031(4) -0.0040(5)
C16 0.0305(8) 0.0209(7) 0.0327(8) 0.0104(6) 0.0000(6) -0.0041(6)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.2136(15) . ?
O2 C5 1.2046(15) . ?
O3 C11 1.3493(16) . ?
O3 C16 1.4345(16) . ?
O4 N2 1.2316(15) . ?
O5 N2 1.2288(14) . ?
N1 C4 1.3956(15) . ?
N1 C5 1.4098(16) . ?
N1 C10 1.4252(15) . ?
N2 C14 1.4634(16) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.5340(19) . ?
C1 C7 1.5394(18) . ?
C2 H2 1.0000 . ?
C2 C3 1.5689(18) . ?
C2 C9 1.518(2) . ?
C3 H3 1.0000 . ?
C3 C4 1.5014(17) . ?
C3 C6 1.5414(17) . ?
C5 C6 1.5129(17) . ?
C6 H6 1.0000 . ?
C6 C7 1.5725(18) . ?
C7 H7 1.0000 . ?
C7 C8 1.5144(19) . ?
C8 H8 0.9500 . ?
C8 C9 1.331(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.4068(17) . ?
C10 C15 1.3808(17) . ?
C11 C12 1.3950(17) . ?
C12 H12 0.9500 . ?
C12 C13 1.3855(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.3834(18) . ?
C14 C15 1.3911(17) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O3 C16 117.79(11) . . ?
C4 N1 C5 113.32(10) . . ?
C4 N1 C10 122.26(10) . . ?
C5 N1 C10 124.18(10) . . ?
O4 N2 C14 118.04(11) . . ?
O5 N2 O4 123.57(11) . . ?
O5 N2 C14 118.38(11) . . ?
H1A C1 H1B 110.3 . . ?
C2 C1 H1A 112.8 . . ?
C2 C1 H1B 112.8 . . ?
C2 C1 C7 94.49(10) . . ?
C7 C1 H1A 112.8 . . ?
C7 C1 H1B 112.8 . . ?
C1 C2 H2 116.2 . . ?
C1 C2 C3 98.43(10) . . ?
C3 C2 H2 116.2 . . ?
C9 C2 C1 100.37(11) . . ?
C9 C2 H2 116.2 . . ?
C9 C2 C3 107.03(10) . . ?
C2 C3 H3 111.1 . . ?
C4 C3 C2 114.04(11) . . ?
C4 C3 H3 111.1 . . ?
C4 C3 C6 105.70(10) . . ?
C6 C3 C2 103.24(10) . . ?
C6 C3 H3 111.1 . . ?
O1 C4 N1 124.28(11) . . ?
O1 C4 C3 127.56(11) . . ?
N1 C4 C3 108.16(10) . . ?
O2 C5 N1 124.09(12) . . ?
O2 C5 C6 128.34(12) . . ?
N1 C5 C6 107.57(10) . . ?
C3 C6 H6 111.1 . . ?
C3 C6 C7 103.05(10) . . ?
C5 C6 C3 105.16(10) . . ?
C5 C6 H6 111.1 . . ?
C5 C6 C7 114.74(10) . . ?
C7 C6 H6 111.1 . . ?
C1 C7 C6 99.16(10) . . ?
C1 C7 H7 116.3 . . ?
C6 C7 H7 116.3 . . ?
C8 C7 C1 100.39(11) . . ?
C8 C7 C6 105.82(10) . . ?
C8 C7 H7 116.3 . . ?
C7 C8 H8 126.1 . . ?
C9 C8 C7 107.74(12) . . ?
C9 C8 H8 126.1 . . ?
C2 C9 H9 126.1 . . ?
C8 C9 C2 107.79(12) . . ?
C8 C9 H9 126.1 . . ?
C11 C10 N1 119.61(11) . . ?
C15 C10 N1 119.90(11) . . ?
C15 C10 C11 120.47(11) . . ?
O3 C11 C10 115.68(11) . . ?
O3 C11 C12 124.58(11) . . ?
C12 C11 C10 119.71(11) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.82(12) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.55(12) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 N2 119.28(11) . . ?
C13 C14 C15 121.72(12) . . ?
C15 C14 N2 118.99(11) . . ?
C10 C15 C14 118.68(11) . . ?
C10 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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
O2 C5 C6 C3 176.72(13) . . . . ?
O2 C5 C6 C7 64.24(17) . . . . ?
O3 C11 C12 C13 -177.95(12) . . . . ?
O4 N2 C14 C13 174.10(12) . . . . ?
O4 N2 C14 C15 -4.87(18) . . . . ?
O5 N2 C14 C13 -5.68(18) . . . . ?
O5 N2 C14 C15 175.36(12) . . . . ?
N1 C5 C6 C3 -2.86(13) . . . . ?
N1 C5 C6 C7 -115.34(11) . . . . ?
N1 C10 C11 O3 1.56(17) . . . . ?
N1 C10 C11 C12 -176.79(11) . . . . ?
N1 C10 C15 C14 176.86(11) . . . . ?
N2 C14 C15 C10 178.56(11) . . . . ?
C1 C2 C3 C4 -152.94(10) . . . . ?
C1 C2 C3 C6 -38.77(12) . . . . ?
C1 C2 C9 C8 32.58(14) . . . . ?
C1 C7 C8 C9 -32.61(13) . . . . ?
C2 C1 C7 C6 -58.93(11) . . . . ?
C2 C1 C7 C8 49.14(12) . . . . ?
C2 C3 C4 O1 -66.26(17) . . . . ?
C2 C3 C4 N1 112.79(12) . . . . ?
C2 C3 C6 C5 -118.38(10) . . . . ?
C2 C3 C6 C7 2.14(12) . . . . ?
C3 C2 C9 C8 -69.66(13) . . . . ?
C3 C6 C7 C1 35.11(11) . . . . ?
C3 C6 C7 C8 -68.51(12) . . . . ?
C4 N1 C5 O2 -176.46(12) . . . . ?
C4 N1 C5 C6 3.14(14) . . . . ?
C4 N1 C10 C11 107.55(14) . . . . ?
C4 N1 C10 C15 -70.64(16) . . . . ?
C4 C3 C6 C5 1.68(13) . . . . ?
C4 C3 C6 C7 122.20(10) . . . . ?
C5 N1 C4 O1 177.05(12) . . . . ?
C5 N1 C4 C3 -2.03(14) . . . . ?
C5 N1 C10 C11 -66.43(16) . . . . ?
C5 N1 C10 C15 115.37(13) . . . . ?
C5 C6 C7 C1 148.83(11) . . . . ?
C5 C6 C7 C8 45.21(14) . . . . ?
C6 C3 C4 O1 -178.97(12) . . . . ?
C6 C3 C4 N1 0.08(13) . . . . ?
C6 C7 C8 C9 70.11(13) . . . . ?
C7 C1 C2 C3 60.14(11) . . . . ?
C7 C1 C2 C9 -49.02(11) . . . . ?
C7 C8 C9 C2 0.09(14) . . . . ?
C9 C2 C3 C4 -49.31(14) . . . . ?
C9 C2 C3 C6 64.86(12) . . . . ?
C10 N1 C4 O1 2.47(19) . . . . ?
C10 N1 C4 C3 -176.61(11) . . . . ?
C10 N1 C5 O2 -2.00(19) . . . . ?
C10 N1 C5 C6 177.60(11) . . . . ?
C10 C11 C12 C13 0.25(19) . . . . ?
C11 C10 C15 C14 -1.33(18) . . . . ?
C11 C12 C13 C14 -1.92(19) . . . . ?
C12 C13 C14 N2 -176.92(11) . . . . ?
C12 C13 C14 C15 2.01(19) . . . . ?
C13 C14 C15 C10 -0.38(19) . . . . ?
C15 C10 C11 O3 179.75(11) . . . . ?
C15 C10 C11 C12 1.40(18) . . . . ?
C16 O3 C11 C10 170.43(12) . . . . ?
C16 O3 C11 C12 -11.31(19) . . . . ?
_shelx_res_file
;
TITL ecv1_121_a.res in P-1
ecv1_121.res
created by SHELXL-2017/1 at 17:40:50 on 20-Nov-2017
REM Old TITL ECV1_121 in P-1
REM SHELXT solution in P-1
REM R1 0.113, Rweak 0.004, Alpha 0.034, Orientation as input
REM Formula found by SHELXT: C17 N O5
REM colorless block
CELL 0.71073 7.7842 9.7899 10.0423 81.677 82.193 67.584
ZERR 2 0.0005 0.0006 0.0006 0.002 0.002 0.002
LATT 1
SFAC C H N O
UNIT 32 28 4 10
L.S. 7
PLAN 9
SIZE 0.36 0.44 0.54
TEMP -173(2)
BOND $H
CONF
list 4
fmap 2
ACTA 60.38
REM
REM
REM
WGHT 0.046100 0.380300
EXTI 0.031091
FVAR 1.06385
O1 4 0.940157 0.187087 0.494482 11.00000 0.01688 0.02406 =
0.01554 -0.00346 -0.00227 -0.00406
O2 4 0.704527 0.177859 0.103857 11.00000 0.01812 0.02171 =
0.01936 -0.00030 -0.00611 -0.00804
O3 4 0.604727 0.476100 0.213011 11.00000 0.01832 0.01713 =
0.02385 0.00452 0.00058 -0.00477
O4 4 0.325871 0.101052 0.683218 11.00000 0.02406 0.02170 =
0.03164 0.00586 0.00487 -0.00313
O5 4 0.104536 0.315547 0.705603 11.00000 0.01652 0.02823 =
0.02388 -0.00478 0.00603 -0.00419
N1 3 0.781832 0.192881 0.314070 11.00000 0.01070 0.01451 =
0.01532 -0.00127 -0.00140 -0.00330
N2 3 0.251538 0.235144 0.649759 11.00000 0.01480 0.02175 =
0.01766 -0.00198 -0.00054 -0.00602
C1 1 1.321984 0.095246 0.106560 11.00000 0.01460 0.02378 =
0.02037 -0.00612 0.00270 -0.00736
AFIX 23
H1A 2 1.382834 -0.014311 0.118896 11.00000 -1.20000
H1B 2 1.408442 0.139299 0.053521 11.00000 -1.20000
AFIX 0
C2 1 1.240149 0.163222 0.240210 11.00000 0.01220 0.02684 =
0.02057 -0.00779 -0.00022 -0.00833
AFIX 13
H2 2 1.332229 0.156110 0.303813 11.00000 -1.20000
AFIX 0
C3 1 1.107800 0.075418 0.290011 11.00000 0.01176 0.01763 =
0.01448 -0.00179 -0.00175 -0.00307
AFIX 13
H3 2 1.178595 -0.026469 0.332202 11.00000 -1.20000
AFIX 0
C4 1 0.941308 0.155859 0.381652 11.00000 0.01257 0.01467 =
0.01542 0.00081 -0.00225 -0.00403
C5 1 0.821067 0.150438 0.181633 11.00000 0.01564 0.01329 =
0.01592 0.00005 -0.00119 -0.00641
C6 1 1.029607 0.068617 0.159138 11.00000 0.01350 0.01468 =
0.01566 -0.00311 -0.00050 -0.00518
AFIX 13
H6 2 1.059915 -0.036478 0.141822 11.00000 -1.20000
AFIX 0
C7 1 1.132069 0.148000 0.047608 11.00000 0.01709 0.02059 =
0.01555 -0.00285 0.00126 -0.00875
AFIX 13
H7 2 1.134932 0.127634 -0.047579 11.00000 -1.20000
AFIX 0
C8 1 1.054564 0.309812 0.074046 11.00000 0.01809 0.01744 =
0.02466 0.00155 0.00134 -0.00819
AFIX 43
H8 2 0.974914 0.390353 0.019314 11.00000 -1.20000
AFIX 0
C9 1 1.118048 0.318974 0.187736 11.00000 0.01888 0.01946 =
0.02913 -0.00888 0.00649 -0.01120
AFIX 43
H9 2 1.091648 0.407227 0.228705 11.00000 -1.20000
AFIX 0
C10 1 0.600395 0.277315 0.370917 11.00000 0.01004 0.01580 =
0.01606 -0.00260 -0.00203 -0.00287
C11 1 0.510296 0.425606 0.318491 11.00000 0.01341 0.01732 =
0.01656 -0.00002 -0.00265 -0.00620
C12 1 0.336777 0.510762 0.378299 11.00000 0.01351 0.01522 =
0.02197 -0.00128 -0.00406 -0.00286
AFIX 43
H12 2 0.275052 0.610841 0.343117 11.00000 -1.20000
AFIX 0
C13 1 0.254695 0.448994 0.489151 11.00000 0.01147 0.01971 =
0.01973 -0.00488 -0.00223 -0.00366
AFIX 43
H13 2 0.138329 0.507298 0.532019 11.00000 -1.20000
AFIX 0
C14 1 0.343343 0.301839 0.536987 11.00000 0.01233 0.01964 =
0.01510 -0.00176 -0.00061 -0.00626
C15 1 0.516479 0.214599 0.479253 11.00000 0.01308 0.01458 =
0.01608 -0.00135 -0.00311 -0.00397
AFIX 43
H15 2 0.575803 0.113875 0.513676 11.00000 -1.20000
AFIX 0
C16 1 0.507848 0.617836 0.142532 11.00000 0.03053 0.02087 =
0.03268 0.01042 0.00001 -0.00408
AFIX 137
H16A 2 0.478095 0.695818 0.202565 11.00000 -1.50000
H16B 2 0.392181 0.618271 0.113902 11.00000 -1.50000
H16C 2 0.587081 0.636252 0.062978 11.00000 -1.50000
AFIX 0
HKLF 4
REM ecv1_121_a.res in P-1
REM R1 = 0.0440 for 3192 Fo > 4sig(Fo) and 0.0645 for all 4121 data
REM 210 parameters refined using 0 restraints
END
WGHT 0.0461 0.3803
REM Highest difference peak 0.384, deepest hole -0.306, 1-sigma level 0.056
Q1 1 0.3009 0.2739 0.5830 11.00000 0.05 0.38
Q2 1 0.3085 0.4763 0.4368 11.00000 0.05 0.37
Q3 1 1.0267 0.1166 0.3330 11.00000 0.05 0.36
Q4 1 0.5470 0.4584 0.2722 11.00000 0.05 0.35
Q5 1 0.5540 0.2498 0.4176 11.00000 0.05 0.34
Q6 1 0.4176 0.4599 0.3486 11.00000 0.05 0.32
Q7 1 0.5541 0.3588 0.3510 11.00000 0.05 0.32
Q8 1 0.4229 0.2579 0.5069 11.00000 0.05 0.32
Q9 1 1.0711 0.0784 0.2287 11.00000 0.05 0.32
;
_shelx_res_checksum 99684
_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_ecv1_169
_database_code_depnum_ccdc_archive 'CCDC 2003348'
loop_
_audit_author_name
_audit_author_address
'Mark D. Smith'
;university of south carolina
United States of America
;
_audit_update_record
;
2020-05-11 deposited with the CCDC. 2020-07-02 downloaded from the CCDC.
;
_audit_creation_date 2017-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number 2017/1
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C15 H12 Cl N O3'
_chemical_formula_sum 'C15 H12 Cl N O3'
_chemical_formula_weight 289.71
_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 0.0033 0.0016 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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 21.3570(9)
_cell_length_b 6.8190(3)
_cell_length_c 20.0691(8)
_cell_angle_alpha 90
_cell_angle_beta 115.0080(10)
_cell_angle_gamma 90
_cell_volume 2648.72(19)
_cell_formula_units_Z 8
_cell_measurement_reflns_used 9958
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 30.01
_cell_measurement_theta_min 2.34
_shelx_estimated_absorpt_T_max 0.977
_shelx_estimated_absorpt_T_min 0.843
_exptl_absorpt_coefficient_mu 0.295
_exptl_absorpt_correction_T_max 0.7460
_exptl_absorpt_correction_T_min 0.7130
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1306 before and 0.0563 after correction.
The Ratio of minimum to maximum transmission is 0.9558.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.453
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description needle
_exptl_crystal_F_000 1200
_exptl_crystal_size_max 0.6
_exptl_crystal_size_mid 0.14
_exptl_crystal_size_min 0.08
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0490
_diffrn_reflns_av_unetI/netI 0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max 29
_diffrn_reflns_limit_h_min -30
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_l_max 28
_diffrn_reflns_limit_l_min -28
_diffrn_reflns_number 61497
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full 30.053
_diffrn_reflns_theta_max 30.053
_diffrn_reflns_theta_min 2.240
_diffrn_ambient_temperature 100(2)
_diffrn_detector 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type 'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device 'three-circle diffractometer'
_diffrn_measurement_device_type 'Bruker D8 QUEST'
_diffrn_measurement_method '\w and \f scans'
_diffrn_radiation_monochromator 'mirror optics'
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'microfocus sealed X-ray tube'
_diffrn_source_type 'Incoatec I\ms'
_diffrn_special_details ?
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 5865
_reflns_number_total 7769
_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 'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection 'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction 'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution 'XT (Sheldrick, 2015)'
_refine_diff_density_max 0.417
_refine_diff_density_min -0.467
_refine_diff_density_rms 0.062
_refine_ls_extinction_coef 0.0048(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method 'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref 1.017
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 370
_refine_ls_number_reflns 7769
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0669
_refine_ls_R_factor_gt 0.0426
_refine_ls_restrained_S_all 1.017
_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/[\s^2^(Fo^2^)+(0.0361P)^2^+2.2210P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0909
_refine_ls_wR_factor_ref 0.1019
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
C2A(H2A), C3A(H3AA), C6A(H6A), C7A(H7A), C2B(H2B), C3B(H3BA), C6B(H6B),
C7B(H7B)
2.b Secondary CH2 refined with riding coordinates:
C1A(H1AA,H1AB), C1B(H1BA,H1BB)
2.c Aromatic/amide H refined with riding coordinates:
C8A(H8A), C9A(H9A), C12A(H12A), C13A(H13A), C15A(H15A), C8B(H8B), C9B(H9B),
C12B(H12B), C13B(H13B), C15B(H15B)
;
_atom_sites_solution_hydrogens mixed
_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
Cl1A Cl -0.15625(2) 0.39535(7) -0.03546(2) 0.02570(10) Uani 1 1 d . . . . .
O1A O 0.03967(6) 0.60561(17) 0.28361(6) 0.0215(2) Uani 1 1 d . . . . .
O2A O 0.09291(6) 0.12408(15) 0.15938(6) 0.0178(2) Uani 1 1 d . . . . .
O3A O 0.10465(5) 0.73673(17) 0.17648(6) 0.0170(2) Uani 1 1 d . . . . .
H3A H 0.1073(12) 0.860(4) 0.1677(12) 0.042(6) Uiso 1 1 d . . . . .
N1A N 0.06056(6) 0.38804(17) 0.20807(6) 0.0117(2) Uani 1 1 d . . . . .
C1A C 0.22137(8) 0.1929(3) 0.40673(9) 0.0270(4) Uani 1 1 d . . . . .
H1AA H 0.200195 0.097685 0.428332 0.032 Uiso 1 1 calc R . . . .
H1AB H 0.271237 0.207965 0.438884 0.032 Uiso 1 1 calc R . . . .
C2A C 0.18267(8) 0.3903(3) 0.38725(8) 0.0212(3) Uani 1 1 d . . . . .
H2A H 0.184913 0.472008 0.429581 0.025 Uiso 1 1 calc R . . . .
C3A C 0.10926(7) 0.3123(2) 0.33392(8) 0.0158(3) Uani 1 1 d . . . . .
H3AA H 0.083604 0.261495 0.362040 0.019 Uiso 1 1 calc R . . . .
C4A C 0.06609(7) 0.4562(2) 0.27592(8) 0.0142(3) Uani 1 1 d . . . . .
C5A C 0.09236(7) 0.2095(2) 0.21260(8) 0.0133(3) Uani 1 1 d . . . . .
C6A C 0.12571(7) 0.1459(2) 0.29190(8) 0.0155(3) Uani 1 1 d . . . . .
H6A H 0.106867 0.017409 0.299171 0.019 Uiso 1 1 calc R . . . .
C7A C 0.20684(8) 0.1443(3) 0.32641(9) 0.0216(3) Uani 1 1 d . . . . .
H7A H 0.228930 0.022413 0.318617 0.026 Uiso 1 1 calc R . . . .
C8A C 0.22829(8) 0.3343(3) 0.30355(9) 0.0230(3) Uani 1 1 d . . . . .
H8A H 0.248523 0.347756 0.269766 0.028 Uiso 1 1 calc R . . . .
C9A C 0.21392(8) 0.4796(3) 0.33896(9) 0.0221(3) Uani 1 1 d . . . . .
H9A H 0.221798 0.615202 0.334786 0.027 Uiso 1 1 calc R . . . .
C10A C 0.02064(7) 0.4864(2) 0.14046(7) 0.0126(3) Uani 1 1 d . . . . .
C11A C 0.04347(7) 0.6662(2) 0.12643(8) 0.0136(3) Uani 1 1 d . . . . .
C12A C 0.00264(8) 0.7636(2) 0.06117(8) 0.0170(3) Uani 1 1 d . . . . .
H12A H 0.017033 0.887323 0.050867 0.020 Uiso 1 1 calc R . . . .
C13A C -0.05861(8) 0.6816(2) 0.01135(8) 0.0182(3) Uani 1 1 d . . . . .
H13A H -0.085984 0.748096 -0.033118 0.022 Uiso 1 1 calc R . . . .
C14A C -0.07962(7) 0.5020(2) 0.02687(8) 0.0169(3) Uani 1 1 d . . . . .
C15A C -0.04076(7) 0.4028(2) 0.09121(8) 0.0150(3) Uani 1 1 d . . . . .
H15A H -0.055730 0.280012 0.101524 0.018 Uiso 1 1 calc R . . . .
Cl1B Cl 0.77046(2) 0.60461(7) 0.38056(2) 0.03096(11) Uani 1 1 d . . . . .
O1B O 0.46656(6) 0.40827(18) 0.22035(6) 0.0237(3) Uani 1 1 d . . . . .
O2B O 0.56202(6) 0.84935(16) 0.12018(6) 0.0204(2) Uani 1 1 d . . . . .
O3B O 0.54561(6) 0.23881(17) 0.12759(6) 0.0194(2) Uani 1 1 d . . . . .
H3B H 0.5544(12) 0.115(4) 0.1205(13) 0.044(7) Uiso 1 1 d . . . . .
N1B N 0.52635(6) 0.60110(18) 0.17306(6) 0.0135(2) Uani 1 1 d . . . . .
C1B C 0.32658(8) 0.7723(3) 0.02126(9) 0.0266(4) Uani 1 1 d . . . . .
H1BA H 0.311740 0.879097 0.044768 0.032 Uiso 1 1 calc R . . . .
H1BB H 0.289991 0.743716 -0.028277 0.032 Uiso 1 1 calc R . . . .
C2B C 0.35102(8) 0.5889(3) 0.06975(9) 0.0231(3) Uani 1 1 d . . . . .
H2B H 0.314747 0.515262 0.078594 0.028 Uiso 1 1 calc R . . . .
C3B C 0.41003(7) 0.6830(2) 0.13912(8) 0.0175(3) Uani 1 1 d . . . . .
H3BA H 0.390940 0.748123 0.171211 0.021 Uiso 1 1 calc R . . . .
C4B C 0.46762(7) 0.5450(2) 0.18265(8) 0.0159(3) Uani 1 1 d . . . . .
C5B C 0.51649(8) 0.7704(2) 0.13212(8) 0.0157(3) Uani 1 1 d . . . . .
C6B C 0.44230(8) 0.8339(2) 0.10602(8) 0.0180(3) Uani 1 1 d . . . . .
H6B H 0.438971 0.969767 0.122989 0.022 Uiso 1 1 calc R . . . .
C7B C 0.39771(8) 0.8112(3) 0.02091(9) 0.0230(3) Uani 1 1 d . . . . .
H7B H 0.400005 0.921941 -0.010640 0.028 Uiso 1 1 calc R . . . .
C8B C 0.41322(8) 0.6087(3) 0.00067(9) 0.0254(4) Uani 1 1 d . . . . .
H8B H 0.437942 0.580494 -0.027966 0.031 Uiso 1 1 calc R . . . .
C9B C 0.38637(8) 0.4781(3) 0.02978(9) 0.0254(4) Uani 1 1 d . . . . .
H9B H 0.388793 0.339568 0.026275 0.030 Uiso 1 1 calc R . . . .
C10B C 0.59131(7) 0.5036(2) 0.20910(8) 0.0140(3) Uani 1 1 d . . . . .
C11B C 0.59965(7) 0.3172(2) 0.18537(8) 0.0159(3) Uani 1 1 d . . . . .
C12B C 0.66289(8) 0.2226(2) 0.22195(9) 0.0198(3) Uani 1 1 d . . . . .
H12B H 0.669696 0.096580 0.205943 0.024 Uiso 1 1 calc R . . . .
C13B C 0.71599(8) 0.3100(3) 0.28140(9) 0.0220(3) Uani 1 1 d . . . . .
H13B H 0.758990 0.244699 0.306076 0.026 Uiso 1 1 calc R . . . .
C14B C 0.70559(7) 0.4942(2) 0.30446(8) 0.0200(3) Uani 1 1 d . . . . .
C15B C 0.64385(7) 0.5927(2) 0.26862(8) 0.0170(3) Uani 1 1 d . . . . .
H15B H 0.637471 0.719376 0.284466 0.020 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
Cl1A 0.01699(17) 0.0368(2) 0.01702(18) -0.00567(16) 0.00111(14) -0.00267(16)
O1A 0.0221(5) 0.0244(6) 0.0176(5) -0.0016(5) 0.0079(4) 0.0082(5)
O2A 0.0247(5) 0.0123(5) 0.0198(5) -0.0010(4) 0.0126(4) 0.0003(4)
O3A 0.0167(5) 0.0118(5) 0.0187(5) 0.0012(4) 0.0040(4) -0.0014(4)
N1A 0.0130(5) 0.0110(5) 0.0106(5) 0.0013(4) 0.0046(4) 0.0009(4)
C1A 0.0176(7) 0.0362(10) 0.0205(8) 0.0086(7) 0.0015(6) 0.0042(7)
C2A 0.0160(7) 0.0294(9) 0.0143(7) -0.0006(6) 0.0025(6) -0.0004(6)
C3A 0.0139(6) 0.0204(8) 0.0128(6) 0.0030(6) 0.0054(5) 0.0005(6)
C4A 0.0117(6) 0.0187(7) 0.0128(6) 0.0000(5) 0.0058(5) -0.0001(5)
C5A 0.0136(6) 0.0103(7) 0.0171(7) 0.0025(5) 0.0076(5) -0.0013(5)
C6A 0.0146(6) 0.0151(7) 0.0169(7) 0.0048(5) 0.0068(5) 0.0014(5)
C7A 0.0140(7) 0.0247(8) 0.0246(8) 0.0056(6) 0.0065(6) 0.0055(6)
C8A 0.0132(7) 0.0300(9) 0.0260(8) 0.0013(7) 0.0085(6) -0.0032(6)
C9A 0.0143(7) 0.0260(8) 0.0223(8) -0.0015(7) 0.0042(6) -0.0063(6)
C10A 0.0140(6) 0.0134(7) 0.0107(6) 0.0009(5) 0.0055(5) 0.0031(5)
C11A 0.0144(6) 0.0138(7) 0.0132(6) -0.0015(5) 0.0062(5) 0.0011(5)
C12A 0.0195(7) 0.0158(7) 0.0166(7) 0.0044(6) 0.0084(6) 0.0033(6)
C13A 0.0197(7) 0.0234(8) 0.0116(6) 0.0041(6) 0.0066(6) 0.0078(6)
C14A 0.0139(6) 0.0233(8) 0.0124(6) -0.0035(6) 0.0047(5) 0.0018(6)
C15A 0.0155(6) 0.0157(7) 0.0142(6) -0.0026(5) 0.0068(5) -0.0007(5)
Cl1B 0.01486(18) 0.0410(3) 0.0285(2) -0.00110(19) 0.00088(15) -0.00670(17)
O1B 0.0178(5) 0.0289(6) 0.0240(6) 0.0103(5) 0.0085(5) -0.0003(5)
O2B 0.0216(5) 0.0148(5) 0.0288(6) 0.0022(4) 0.0146(5) -0.0006(4)
O3B 0.0217(5) 0.0144(6) 0.0197(5) -0.0023(4) 0.0064(4) 0.0005(4)
N1B 0.0114(5) 0.0137(6) 0.0145(5) 0.0013(5) 0.0047(4) 0.0002(5)
C1B 0.0189(7) 0.0350(10) 0.0216(8) 0.0053(7) 0.0045(6) 0.0091(7)
C2B 0.0131(7) 0.0304(9) 0.0217(8) 0.0029(7) 0.0035(6) 0.0014(6)
C3B 0.0139(6) 0.0232(8) 0.0166(7) 0.0017(6) 0.0076(6) 0.0031(6)
C4B 0.0141(6) 0.0187(7) 0.0148(6) -0.0003(6) 0.0059(5) -0.0004(5)
C5B 0.0188(7) 0.0121(7) 0.0168(7) -0.0006(5) 0.0081(6) 0.0011(5)
C6B 0.0177(7) 0.0166(7) 0.0202(7) 0.0027(6) 0.0084(6) 0.0048(6)
C7B 0.0211(7) 0.0284(9) 0.0181(7) 0.0087(7) 0.0069(6) 0.0079(7)
C8B 0.0220(8) 0.0367(10) 0.0139(7) -0.0021(7) 0.0040(6) 0.0073(7)
C9B 0.0183(7) 0.0281(9) 0.0199(8) -0.0050(7) -0.0016(6) 0.0017(7)
C10B 0.0107(6) 0.0154(7) 0.0161(6) 0.0026(5) 0.0059(5) 0.0013(5)
C11B 0.0163(7) 0.0167(7) 0.0165(7) 0.0025(6) 0.0087(6) 0.0004(6)
C12B 0.0209(7) 0.0183(8) 0.0252(8) 0.0048(6) 0.0145(6) 0.0059(6)
C13B 0.0139(7) 0.0272(9) 0.0273(8) 0.0094(7) 0.0109(6) 0.0057(6)
C14B 0.0115(6) 0.0257(8) 0.0204(7) 0.0028(6) 0.0046(6) -0.0033(6)
C15B 0.0148(6) 0.0166(7) 0.0200(7) -0.0002(6) 0.0078(6) -0.0021(6)
_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
Cl1A C14A 1.7439(15) . ?
O1A C4A 1.2057(18) . ?
O2A C5A 1.2209(18) . ?
O3A H3A 0.86(3) . ?
O3A C11A 1.3555(17) . ?
N1A C4A 1.3958(18) . ?
N1A C5A 1.3784(18) . ?
N1A C10A 1.4283(17) . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?
C1A C2A 1.541(2) . ?
C1A C7A 1.543(2) . ?
C2A H2A 1.0000 . ?
C2A C3A 1.571(2) . ?
C2A C9A 1.517(2) . ?
C3A H3AA 1.0000 . ?
C3A C4A 1.504(2) . ?
C3A C6A 1.540(2) . ?
C5A C6A 1.507(2) . ?
C6A H6A 1.0000 . ?
C6A C7A 1.571(2) . ?
C7A H7A 1.0000 . ?
C7A C8A 1.509(2) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.328(2) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.392(2) . ?
C10A C15A 1.3876(19) . ?
C11A C12A 1.397(2) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.385(2) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.385(2) . ?
C14A C15A 1.381(2) . ?
C15A H15A 0.9500 . ?
Cl1B C14B 1.7407(16) . ?
O1B C4B 1.2071(19) . ?
O2B C5B 1.2205(18) . ?
O3B H3B 0.89(3) . ?
O3B C11B 1.3532(18) . ?
N1B C4B 1.4003(18) . ?
N1B C5B 1.3806(19) . ?
N1B C10B 1.4287(18) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
C1B C2B 1.534(2) . ?
C1B C7B 1.545(2) . ?
C2B H2B 1.0000 . ?
C2B C3B 1.567(2) . ?
C2B C9B 1.515(2) . ?
C3B H3BA 1.0000 . ?
C3B C4B 1.501(2) . ?
C3B C6B 1.537(2) . ?
C5B C6B 1.507(2) . ?
C6B H6B 1.0000 . ?
C6B C7B 1.573(2) . ?
C7B H7B 1.0000 . ?
C7B C8B 1.515(2) . ?
C8B H8B 0.9500 . ?
C8B C9B 1.322(3) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.395(2) . ?
C10B C15B 1.386(2) . ?
C11B C12B 1.393(2) . ?
C12B H12B 0.9500 . ?
C12B C13B 1.386(2) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.388(2) . ?
C14B C15B 1.380(2) . ?
C15B H15B 0.9500 . ?
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
C11A O3A H3A 108.6(15) . . ?
C4A N1A C10A 122.73(12) . . ?
C5A N1A C4A 113.19(12) . . ?
C5A N1A C10A 123.86(12) . . ?
H1AA C1A H1AB 110.3 . . ?
C2A C1A H1AA 112.9 . . ?
C2A C1A H1AB 112.9 . . ?
C2A C1A C7A 94.20(12) . . ?
C7A C1A H1AA 112.9 . . ?
C7A C1A H1AB 112.9 . . ?
C1A C2A H2A 116.3 . . ?
C1A C2A C3A 98.67(13) . . ?
C3A C2A H2A 116.3 . . ?
C9A C2A C1A 100.31(13) . . ?
C9A C2A H2A 116.3 . . ?
C9A C2A C3A 106.41(12) . . ?
C2A C3A H3AA 111.1 . . ?
C4A C3A C2A 114.52(13) . . ?
C4A C3A H3AA 111.1 . . ?
C4A C3A C6A 105.32(11) . . ?
C6A C3A C2A 103.28(12) . . ?
C6A C3A H3AA 111.1 . . ?
O1A C4A N1A 123.72(13) . . ?
O1A C4A C3A 128.27(13) . . ?
N1A C4A C3A 108.01(12) . . ?
O2A C5A N1A 123.39(13) . . ?
O2A C5A C6A 127.71(13) . . ?
N1A C5A C6A 108.88(12) . . ?
C3A C6A H6A 111.5 . . ?
C3A C6A C7A 103.18(12) . . ?
C5A C6A C3A 104.53(12) . . ?
C5A C6A H6A 111.5 . . ?
C5A C6A C7A 114.10(12) . . ?
C7A C6A H6A 111.5 . . ?
C1A C7A C6A 98.99(12) . . ?
C1A C7A H7A 116.2 . . ?
C6A C7A H7A 116.2 . . ?
C8A C7A C1A 100.37(14) . . ?
C8A C7A C6A 106.27(12) . . ?
C8A C7A H7A 116.2 . . ?
C7A C8A H8A 126.0 . . ?
C9A C8A C7A 108.01(14) . . ?
C9A C8A H8A 126.0 . . ?
C2A C9A H9A 126.1 . . ?
C8A C9A C2A 107.82(15) . . ?
C8A C9A H9A 126.1 . . ?
C11A C10A N1A 119.11(12) . . ?
C15A C10A N1A 119.25(13) . . ?
C15A C10A C11A 121.62(13) . . ?
O3A C11A C10A 118.22(13) . . ?
O3A C11A C12A 123.39(14) . . ?
C10A C11A C12A 118.38(13) . . ?
C11A C12A H12A 119.7 . . ?
C13A C12A C11A 120.65(14) . . ?
C13A C12A H12A 119.7 . . ?
C12A C13A H13A 120.3 . . ?
C14A C13A C12A 119.46(14) . . ?
C14A C13A H13A 120.3 . . ?
C13A C14A Cl1A 120.17(11) . . ?
C15A C14A Cl1A 118.53(12) . . ?
C15A C14A C13A 121.30(14) . . ?
C10A C15A H15A 120.7 . . ?
C14A C15A C10A 118.58(14) . . ?
C14A C15A H15A 120.7 . . ?
C11B O3B H3B 110.5(15) . . ?
C4B N1B C10B 122.53(12) . . ?
C5B N1B C4B 112.96(12) . . ?
C5B N1B C10B 124.16(12) . . ?
H1BA C1B H1BB 110.3 . . ?
C2B C1B H1BA 112.9 . . ?
C2B C1B H1BB 112.9 . . ?
C2B C1B C7B 94.09(12) . . ?
C7B C1B H1BA 112.9 . . ?
C7B C1B H1BB 112.9 . . ?
C1B C2B H2B 116.1 . . ?
C1B C2B C3B 99.20(14) . . ?
C3B C2B H2B 116.1 . . ?
C9B C2B C1B 100.53(14) . . ?
C9B C2B H2B 116.1 . . ?
C9B C2B C3B 106.33(12) . . ?
C2B C3B H3BA 111.1 . . ?
C4B C3B C2B 114.44(13) . . ?
C4B C3B H3BA 111.1 . . ?
C4B C3B C6B 105.32(11) . . ?
C6B C3B C2B 103.26(12) . . ?
C6B C3B H3BA 111.1 . . ?
O1B C4B N1B 123.54(14) . . ?
O1B C4B C3B 128.39(13) . . ?
N1B C4B C3B 108.06(12) . . ?
O2B C5B N1B 123.50(13) . . ?
O2B C5B C6B 127.81(14) . . ?
N1B C5B C6B 108.69(12) . . ?
C3B C6B H6B 111.3 . . ?
C3B C6B C7B 103.13(12) . . ?
C5B C6B C3B 104.79(12) . . ?
C5B C6B H6B 111.3 . . ?
C5B C6B C7B 114.47(12) . . ?
C7B C6B H6B 111.3 . . ?
C1B C7B C6B 99.03(12) . . ?
C1B C7B H7B 116.4 . . ?
C6B C7B H7B 116.4 . . ?
C8B C7B C1B 99.88(14) . . ?
C8B C7B C6B 106.28(12) . . ?
C8B C7B H7B 116.4 . . ?
C7B C8B H8B 125.9 . . ?
C9B C8B C7B 108.11(15) . . ?
C9B C8B H8B 125.9 . . ?
C2B C9B H9B 126.1 . . ?
C8B C9B C2B 107.71(16) . . ?
C8B C9B H9B 126.1 . . ?
C11B C10B N1B 119.21(13) . . ?
C15B C10B N1B 119.43(13) . . ?
C15B C10B C11B 121.32(13) . . ?
O3B C11B C10B 117.83(13) . . ?
O3B C11B C12B 123.66(14) . . ?
C12B C11B C10B 118.51(14) . . ?
C11B C12B H12B 119.6 . . ?
C13B C12B C11B 120.84(15) . . ?
C13B C12B H12B 119.6 . . ?
C12B C13B H13B 120.4 . . ?
C12B C13B C14B 119.20(14) . . ?
C14B C13B H13B 120.4 . . ?
C13B C14B Cl1B 120.24(12) . . ?
C15B C14B Cl1B 118.51(13) . . ?
C15B C14B C13B 121.25(14) . . ?
C10B C15B H15B 120.6 . . ?
C14B C15B C10B 118.86(14) . . ?
C14B C15B H15B 120.6 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3A H3A O2A 0.86(3) 1.83(3) 2.6617(16) 163(2) 1_565 yes
O3B H3B O2B 0.89(3) 1.82(3) 2.6911(16) 166(2) 1_545 yes
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
Cl1A C14A C15A C10A 179.26(11) . . . . ?
O2A C5A C6A C3A 178.78(14) . . . . ?
O2A C5A C6A C7A 66.8(2) . . . . ?
O3A C11A C12A C13A 178.42(13) . . . . ?
N1A C5A C6A C3A -0.06(15) . . . . ?
N1A C5A C6A C7A -112.02(14) . . . . ?
N1A C10A C11A O3A 2.87(19) . . . . ?
N1A C10A C11A C12A -177.87(12) . . . . ?
N1A C10A C15A C14A 178.46(12) . . . . ?
C1A C2A C3A C4A -151.66(13) . . . . ?
C1A C2A C3A C6A -37.71(14) . . . . ?
C1A C2A C9A C8A 32.41(16) . . . . ?
C1A C7A C8A C9A -32.97(16) . . . . ?
C2A C1A C7A C6A -59.31(14) . . . . ?
C2A C1A C7A C8A 49.18(13) . . . . ?
C2A C3A C4A O1A -70.0(2) . . . . ?
C2A C3A C4A N1A 110.12(14) . . . . ?
C2A C3A C6A C5A -118.84(12) . . . . ?
C2A C3A C6A C7A 0.76(14) . . . . ?
C3A C2A C9A C8A -69.91(16) . . . . ?
C3A C6A C7A C1A 36.39(15) . . . . ?
C3A C6A C7A C8A -67.26(15) . . . . ?
C4A N1A C5A O2A 179.39(13) . . . . ?
C4A N1A C5A C6A -1.71(16) . . . . ?
C4A N1A C10A C11A 69.99(17) . . . . ?
C4A N1A C10A C15A -108.46(16) . . . . ?
C4A C3A C6A C5A 1.61(14) . . . . ?
C4A C3A C6A C7A 121.21(12) . . . . ?
C5A N1A C4A O1A -177.09(13) . . . . ?
C5A N1A C4A C3A 2.78(16) . . . . ?
C5A N1A C10A C11A -115.78(15) . . . . ?
C5A N1A C10A C15A 65.77(18) . . . . ?
C5A C6A C7A C1A 149.17(13) . . . . ?
C5A C6A C7A C8A 45.51(17) . . . . ?
C6A C3A C4A O1A 177.25(14) . . . . ?
C6A C3A C4A N1A -2.63(15) . . . . ?
C6A C7A C8A C9A 69.67(16) . . . . ?
C7A C1A C2A C3A 59.69(13) . . . . ?
C7A C1A C2A C9A -48.86(14) . . . . ?
C7A C8A C9A C2A 0.38(17) . . . . ?
C9A C2A C3A C4A -48.14(17) . . . . ?
C9A C2A C3A C6A 65.80(15) . . . . ?
C10A N1A C4A O1A -2.3(2) . . . . ?
C10A N1A C4A C3A 177.57(12) . . . . ?
C10A N1A C5A O2A 4.7(2) . . . . ?
C10A N1A C5A C6A -176.43(12) . . . . ?
C10A C11A C12A C13A -0.8(2) . . . . ?
C11A C10A C15A C14A 0.1(2) . . . . ?
C11A C12A C13A C14A 0.5(2) . . . . ?
C12A C13A C14A Cl1A -179.51(11) . . . . ?
C12A C13A C14A C15A 0.1(2) . . . . ?
C13A C14A C15A C10A -0.4(2) . . . . ?
C15A C10A C11A O3A -178.72(13) . . . . ?
C15A C10A C11A C12A 0.5(2) . . . . ?
Cl1B C14B C15B C10B -178.39(11) . . . . ?
O2B C5B C6B C3B -178.69(15) . . . . ?
O2B C5B C6B C7B 69.1(2) . . . . ?
O3B C11B C12B C13B -179.22(14) . . . . ?
N1B C5B C6B C3B 1.78(16) . . . . ?
N1B C5B C6B C7B -110.45(15) . . . . ?
N1B C10B C11B O3B 1.47(19) . . . . ?
N1B C10B C11B C12B -178.84(13) . . . . ?
N1B C10B C15B C14B 177.90(13) . . . . ?
C1B C2B C3B C4B -151.44(13) . . . . ?
C1B C2B C3B C6B -37.53(14) . . . . ?
C1B C2B C9B C8B 32.44(16) . . . . ?
C1B C7B C8B C9B -33.34(16) . . . . ?
C2B C1B C7B C6B -59.01(14) . . . . ?
C2B C1B C7B C8B 49.40(14) . . . . ?
C2B C3B C4B O1B -70.6(2) . . . . ?
C2B C3B C4B N1B 109.73(14) . . . . ?
C2B C3B C6B C5B -119.62(13) . . . . ?
C2B C3B C6B C7B 0.47(15) . . . . ?
C3B C2B C9B C8B -70.51(16) . . . . ?
C3B C6B C7B C1B 36.40(15) . . . . ?
C3B C6B C7B C8B -66.74(15) . . . . ?
C4B N1B C5B O2B 176.53(14) . . . . ?
C4B N1B C5B C6B -3.91(17) . . . . ?
C4B N1B C10B C11B 73.15(18) . . . . ?
C4B N1B C10B C15B -104.42(17) . . . . ?
C4B C3B C6B C5B 0.73(15) . . . . ?
C4B C3B C6B C7B 120.82(13) . . . . ?
C5B N1B C4B O1B -175.36(14) . . . . ?
C5B N1B C4B C3B 4.38(17) . . . . ?
C5B N1B C10B C11B -114.03(16) . . . . ?
C5B N1B C10B C15B 68.40(19) . . . . ?
C5B C6B C7B C1B 149.62(14) . . . . ?
C5B C6B C7B C8B 46.47(18) . . . . ?
C6B C3B C4B O1B 176.76(16) . . . . ?
C6B C3B C4B N1B -2.96(16) . . . . ?
C6B C7B C8B C9B 69.18(16) . . . . ?
C7B C1B C2B C3B 59.44(14) . . . . ?
C7B C1B C2B C9B -49.21(14) . . . . ?
C7B C8B C9B C2B 0.76(17) . . . . ?
C9B C2B C3B C4B -47.53(17) . . . . ?
C9B C2B C3B C6B 66.38(16) . . . . ?
C10B N1B C4B O1B -1.8(2) . . . . ?
C10B N1B C4B C3B 177.93(13) . . . . ?
C10B N1B C5B O2B 3.1(2) . . . . ?
C10B N1B C5B C6B -177.34(13) . . . . ?
C10B C11B C12B C13B 1.1(2) . . . . ?
C11B C10B C15B C14B 0.4(2) . . . . ?
C11B C12B C13B C14B 0.0(2) . . . . ?
C12B C13B C14B Cl1B 178.16(12) . . . . ?
C12B C13B C14B C15B -1.0(2) . . . . ?
C13B C14B C15B C10B 0.8(2) . . . . ?
C15B C10B C11B O3B 178.99(13) . . . . ?
C15B C10B C11B C12B -1.3(2) . . . . ?
_shelx_res_file
;
TITL ecv1_169_a.res in P2(1)/c
ecv1_169.res
created by SHELXL-2017/1 at 17:10:40 on 22-Nov-2017
REM Old TITL ECV1_169 in P2(1)/c
REM SHELXT solution in P2(1)/c
REM R1 0.119, Rweak 0.004, Alpha 0.021, Orientation as input
REM Formula found by SHELXT: C30 N2 O6 Cl1B
CELL 0.71073 21.357 6.819 20.0691 90 115.008 90
ZERR 8 0.0009 0.0003 0.0008 0 0.001 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Cl N O
UNIT 120 96 8 8 24
EQIV $1 +X,1+Y,+Z
EQIV $2 +X,-1+Y,+Z
L.S. 7
PLAN 9
SIZE 0.08 0.14 0.6
TEMP -173(2)
HTAB O3A O2A_$1
HTAB O3B O2B_$2
BOND $H
CONF
list 4
fmap 2
ACTA 60.11
REM
REM
REM
WGHT 0.036100 2.221000
EXTI 0.004847
FVAR 0.57838
CL1A 3 -0.156254 0.395346 -0.035464 11.00000 0.01699 0.03683 =
0.01702 -0.00567 0.00111 -0.00267
O1A 5 0.039671 0.605610 0.283610 11.00000 0.02208 0.02444 =
0.01756 -0.00164 0.00789 0.00817
O2A 5 0.092911 0.124077 0.159381 11.00000 0.02468 0.01232 =
0.01981 -0.00103 0.01264 0.00028
O3A 5 0.104648 0.736730 0.176483 11.00000 0.01673 0.01185 =
0.01874 0.00121 0.00404 -0.00144
H3A 2 0.107331 0.859511 0.167735 11.00000 0.04176
N1A 4 0.060559 0.388040 0.208069 11.00000 0.01304 0.01099 =
0.01065 0.00125 0.00464 0.00093
C1A 1 0.221370 0.192943 0.406733 11.00000 0.01763 0.03619 =
0.02052 0.00857 0.00147 0.00421
AFIX 23
H1AA 2 0.200195 0.097685 0.428332 11.00000 -1.20000
H1AB 2 0.271237 0.207965 0.438884 11.00000 -1.20000
AFIX 0
C2A 1 0.182668 0.390310 0.387249 11.00000 0.01605 0.02939 =
0.01430 -0.00059 0.00254 -0.00041
AFIX 13
H2A 2 0.184913 0.472008 0.429581 11.00000 -1.20000
AFIX 0
C3A 1 0.109261 0.312276 0.333922 11.00000 0.01393 0.02044 =
0.01277 0.00301 0.00542 0.00055
AFIX 13
H3AA 2 0.083604 0.261495 0.362040 11.00000 -1.20000
AFIX 0
C4A 1 0.066092 0.456205 0.275919 11.00000 0.01173 0.01870 =
0.01281 -0.00004 0.00580 -0.00009
C5A 1 0.092358 0.209469 0.212597 11.00000 0.01359 0.01028 =
0.01710 0.00248 0.00756 -0.00126
C6A 1 0.125706 0.145862 0.291905 11.00000 0.01464 0.01509 =
0.01693 0.00476 0.00681 0.00144
AFIX 13
H6A 2 0.106867 0.017409 0.299171 11.00000 -1.20000
AFIX 0
C7A 1 0.206839 0.144280 0.326410 11.00000 0.01395 0.02466 =
0.02455 0.00562 0.00649 0.00545
AFIX 13
H7A 2 0.228930 0.022413 0.318617 11.00000 -1.20000
AFIX 0
C8A 1 0.228291 0.334344 0.303550 11.00000 0.01316 0.02997 =
0.02602 0.00131 0.00846 -0.00317
AFIX 43
H8A 2 0.248523 0.347756 0.269766 11.00000 -1.20000
AFIX 0
C9A 1 0.213916 0.479582 0.338958 11.00000 0.01432 0.02604 =
0.02231 -0.00152 0.00417 -0.00628
AFIX 43
H9A 2 0.221798 0.615202 0.334786 11.00000 -1.20000
AFIX 0
C10A 1 0.020637 0.486418 0.140459 11.00000 0.01401 0.01340 =
0.01066 0.00093 0.00548 0.00308
C11A 1 0.043473 0.666241 0.126427 11.00000 0.01437 0.01376 =
0.01320 -0.00148 0.00620 0.00114
C12A 1 0.002643 0.763621 0.061172 11.00000 0.01951 0.01576 =
0.01657 0.00435 0.00835 0.00329
AFIX 43
H12A 2 0.017033 0.887323 0.050867 11.00000 -1.20000
AFIX 0
C13A 1 -0.058606 0.681633 0.011349 11.00000 0.01968 0.02342 =
0.01156 0.00414 0.00659 0.00780
AFIX 43
H13A 2 -0.085984 0.748096 -0.033118 11.00000 -1.20000
AFIX 0
C14A 1 -0.079622 0.501961 0.026873 11.00000 0.01393 0.02333 =
0.01237 -0.00349 0.00465 0.00175
C15A 1 -0.040755 0.402826 0.091206 11.00000 0.01553 0.01575 =
0.01420 -0.00260 0.00680 -0.00071
AFIX 43
H15A 2 -0.055730 0.280012 0.101524 11.00000 -1.20000
AFIX 0
CL1B 3 0.770456 0.604608 0.380565 11.00000 0.01486 0.04102 =
0.02849 -0.00110 0.00088 -0.00670
O1B 5 0.466558 0.408265 0.220355 11.00000 0.01783 0.02888 =
0.02405 0.01030 0.00851 -0.00031
O2B 5 0.562024 0.849349 0.120184 11.00000 0.02162 0.01485 =
0.02882 0.00215 0.01461 -0.00061
O3B 5 0.545609 0.238809 0.127591 11.00000 0.02167 0.01443 =
0.01975 -0.00225 0.00642 0.00045
H3B 2 0.554371 0.115280 0.120529 11.00000 0.04425
N1B 4 0.526353 0.601104 0.173061 11.00000 0.01142 0.01365 =
0.01449 0.00135 0.00466 0.00019
C1B 1 0.326578 0.772257 0.021263 11.00000 0.01895 0.03505 =
0.02158 0.00534 0.00450 0.00911
AFIX 23
H1BA 2 0.311740 0.879097 0.044768 11.00000 -1.20000
H1BB 2 0.289991 0.743716 -0.028277 11.00000 -1.20000
AFIX 0
C2B 1 0.351023 0.588879 0.069750 11.00000 0.01309 0.03037 =
0.02172 0.00291 0.00347 0.00144
AFIX 13
H2B 2 0.314747 0.515262 0.078594 11.00000 -1.20000
AFIX 0
C3B 1 0.410026 0.683000 0.139124 11.00000 0.01393 0.02317 =
0.01658 0.00172 0.00756 0.00312
AFIX 13
H3BA 2 0.390940 0.748123 0.171211 11.00000 -1.20000
AFIX 0
C4B 1 0.467624 0.545009 0.182651 11.00000 0.01413 0.01869 =
0.01475 -0.00031 0.00589 -0.00038
C5B 1 0.516494 0.770409 0.132121 11.00000 0.01879 0.01209 =
0.01677 -0.00057 0.00806 0.00115
C6B 1 0.442304 0.833890 0.106021 11.00000 0.01766 0.01655 =
0.02020 0.00265 0.00843 0.00483
AFIX 13
H6B 2 0.438971 0.969767 0.122989 11.00000 -1.20000
AFIX 0
C7B 1 0.397714 0.811167 0.020906 11.00000 0.02109 0.02844 =
0.01812 0.00869 0.00687 0.00789
AFIX 13
H7B 2 0.400005 0.921941 -0.010640 11.00000 -1.20000
AFIX 0
C8B 1 0.413220 0.608681 0.000668 11.00000 0.02204 0.03670 =
0.01387 -0.00214 0.00404 0.00726
AFIX 43
H8B 2 0.437942 0.580494 -0.027966 11.00000 -1.20000
AFIX 0
C9B 1 0.386369 0.478056 0.029779 11.00000 0.01826 0.02807 =
0.01986 -0.00501 -0.00157 0.00168
AFIX 43
H9B 2 0.388793 0.339568 0.026275 11.00000 -1.20000
AFIX 0
C10B 1 0.591308 0.503608 0.209098 11.00000 0.01074 0.01536 =
0.01611 0.00264 0.00594 0.00126
C11B 1 0.599651 0.317220 0.185372 11.00000 0.01633 0.01667 =
0.01647 0.00255 0.00873 0.00041
C12B 1 0.662887 0.222615 0.221952 11.00000 0.02093 0.01827 =
0.02518 0.00481 0.01447 0.00585
AFIX 43
H12B 2 0.669696 0.096580 0.205943 11.00000 -1.20000
AFIX 0
C13B 1 0.715990 0.310022 0.281401 11.00000 0.01393 0.02716 =
0.02727 0.00943 0.01090 0.00568
AFIX 43
H13B 2 0.758990 0.244699 0.306076 11.00000 -1.20000
AFIX 0
C14B 1 0.705589 0.494195 0.304457 11.00000 0.01153 0.02573 =
0.02042 0.00277 0.00462 -0.00328
C15B 1 0.643848 0.592701 0.268617 11.00000 0.01477 0.01659 =
0.02003 -0.00020 0.00785 -0.00209
AFIX 43
H15B 2 0.637471 0.719376 0.284466 11.00000 -1.20000
AFIX 0
HKLF 4
REM ecv1_169_a.res in P2(1)/c
REM R1 = 0.0426 for 5865 Fo > 4sig(Fo) and 0.0669 for all 7769 data
REM 370 parameters refined using 0 restraints
END
WGHT 0.0361 2.2209
REM Highest difference peak 0.417, deepest hole -0.467, 1-sigma level 0.062
Q1 1 0.1102 0.1731 0.2527 11.00000 0.05 0.42
Q2 1 0.5944 0.4180 0.1908 11.00000 0.05 0.37
Q3 1 0.0397 0.5563 0.1274 11.00000 0.05 0.37
Q4 1 0.2199 0.2305 0.3117 11.00000 0.05 0.34
Q5 1 0.4770 0.8152 0.1130 11.00000 0.05 0.34
Q6 1 0.1446 0.3667 0.3594 11.00000 0.05 0.34
Q7 1 0.0885 0.3808 0.3065 11.00000 0.05 0.34
Q8 1 0.7491 0.7190 0.3757 11.00000 0.05 0.32
Q9 1 0.2192 0.1565 0.3650 11.00000 0.05 0.32
;
_shelx_res_checksum 33000
_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_ecv1_125_a
_database_code_depnum_ccdc_archive 'CCDC 2003345'
loop_
_audit_author_name
_audit_author_address
'Mark D. Smith'
;university of south carolina
United States of America
;
_audit_update_record
;
2020-05-11 deposited with the CCDC. 2020-07-02 downloaded from the CCDC.
;
_audit_creation_date 2017-02-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number 2016/6
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C15 H12 Cl N O3'
_chemical_formula_sum 'C15 H12 Cl N O3'
_chemical_formula_weight 289.71
_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 0.0033 0.0016 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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 17.4699(12)
_cell_length_b 6.8917(5)
_cell_length_c 22.137(2)
_cell_angle_alpha 90
_cell_angle_beta 103.5700(16)
_cell_angle_gamma 90
_cell_volume 2590.8(3)
_cell_formula_units_Z 8
_cell_measurement_reflns_used 9909
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 27.70
_cell_measurement_theta_min 2.40
_shelx_estimated_absorpt_T_max 0.982
_shelx_estimated_absorpt_T_min 0.920
_exptl_absorpt_coefficient_mu 0.301
_exptl_absorpt_correction_T_max 0.8621
_exptl_absorpt_correction_T_min 0.8136
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1270 before and 0.0579 after correction.
The Ratio of minimum to maximum transmission is 0.9437.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.485
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description plate
_exptl_crystal_F_000 1200
_exptl_crystal_size_max 0.28
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_min 0.06
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0385
_diffrn_reflns_av_unetI/netI 0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max 22
_diffrn_reflns_limit_h_min -22
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_l_max 28
_diffrn_reflns_limit_l_min -28
_diffrn_reflns_number 49286
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full 27.723
_diffrn_reflns_theta_max 27.723
_diffrn_reflns_theta_min 2.399
_diffrn_ambient_temperature 100(2)
_diffrn_detector 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type 'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device 'three-circle diffractometer'
_diffrn_measurement_device_type 'Bruker D8 Quest'
_diffrn_measurement_method '\w and \f scans'
_diffrn_radiation_monochromator 'mirror optics'
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'microfocus sealed X-ray tube'
_diffrn_source_type 'Incoatec I\ms'
_diffrn_special_details ?
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2832
_reflns_number_total 3036
_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 'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection 'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction 'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution 'XS (Sheldrick, 2008)'
_refine_diff_density_max 0.350
_refine_diff_density_min -0.291
_refine_diff_density_rms 0.062
_refine_ls_extinction_coef 0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method 'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref 1.301
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 272
_refine_ls_number_reflns 3036
_refine_ls_number_restraints 64
_refine_ls_R_factor_all 0.0557
_refine_ls_R_factor_gt 0.0524
_refine_ls_restrained_S_all 1.294
_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^)+(0.0277P)^2^+7.6465P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1264
_refine_ls_wR_factor_ref 0.1277
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
2. Restrained distances
N1B-C10B \\sim N1-C10
with sigma of 0.01
O3A-C11 \\sim O3C-C15 \\sim O3D-C15B \\sim O3C-C11B
with sigma of 0.01
3. Restrained planarity
C12B, C13B, C14B, C15B, C10B, C11B
with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C3) = Uanis(C6B)
Uanis(C12) = Uanis(C12B)
Uanis(Cl1) = Uanis(Cl1B)
Uanis(N1) = Uanis(N1B)
5. Same fragment restrains
{O1, O2, N1, C1, C2, C3, C4, C5, C6, C7, C8, C9} sigma for 1-2: 0.015, 1-3: 0.04
as
{O1B, O2B, N1B, C1B, C2B, C3B, C4B, C5B, C6B, C7B, C8B, C9B}
{Cl1, O3A, O3C, C10, C11, C12, C13, C14, C15} sigma for 1-2: 0.015, 1-3: 0.04
as
{Cl1B, O3B, O3D, C10B, C11B, C12B, C13B, C14B, C15B}
6. Others
Sof(O1B)=Sof(O2B)=Sof(N1B)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(C2B)=Sof(H2B)=
Sof(C3B)=Sof(H3BA)=Sof(C4B)=Sof(C5B)=Sof(C6B)=Sof(H6B)=Sof(C7B)=Sof(H7B)=
Sof(C8B)=Sof(H8B)=Sof(C9B)=Sof(H9B)=Sof(Cl1B)=Sof(C10B)=Sof(C11B)=Sof(C12B)=
Sof(H12B)=Sof(C13B)=Sof(C14B)=Sof(H14B)=Sof(C15B)=1-FVAR(1)
Sof(O3B)=Sof(H15B)=0.6*(1-FVAR(2))
Sof(O3D)=Sof(H11B)=0.4*(1-FVAR(2))
Sof(O3A)=Sof(O3C)=Sof(H11)=Sof(H15)=0.5*FVAR(2)
Sof(O1)=Sof(O2)=Sof(N1)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(C2)=Sof(H2)=Sof(C3)=
Sof(H3)=Sof(C4)=Sof(C5)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=
Sof(C9)=Sof(H9)=Sof(Cl1)=Sof(C10)=Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(C14)=
Sof(H14)=Sof(C15)=FVAR(1)
7.a Riding coordinates:
C11(H11), C15(H15), C11B(H11B), C15B(H15B)
7.b Ternary CH refined with riding coordinates:
C2(H2), C3(H3), C6(H6), C7(H7), C2B(H2B), C3B(H3BA), C6B(H6B), C7B(H7B)
7.c Secondary CH2 refined with riding coordinates:
C1(H1A,H1B), C1B(H1BA,H1BB)
7.d Aromatic/amide H refined with riding coordinates:
C8(H8), C9(H9), C8B(H8B), C9B(H9B), C12(H12), C14(H14), C12B(H12B), C14B(H14B)
;
_atom_sites_solution_hydrogens mixed
_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
O1 O 0.02064(10) 0.5542(3) 0.28315(8) 0.0213(4) Uani 0.879(2) 1 d D . P A 1
O2 O 0.18528(10) 0.0848(2) 0.24349(8) 0.0165(4) Uani 0.879(2) 1 d D . P A 1
N1 N 0.10622(12) 0.3435(3) 0.25309(9) 0.0118(4) Uani 0.879(2) 1 d D . P A 1
C1 C 0.14343(15) 0.1513(4) 0.43995(11) 0.0204(5) Uani 0.879(2) 1 d D . P A 1
H1A H 0.102908 0.050674 0.439649 0.024 Uiso 0.879(2) 1 calc R . P A 1
H1B H 0.176506 0.168578 0.482505 0.024 Uiso 0.879(2) 1 calc R . P A 1
C2 C 0.10857(15) 0.3433(4) 0.41008(11) 0.0182(5) Uani 0.879(2) 1 d D . P A 1
H2 H 0.074674 0.416855 0.432802 0.022 Uiso 0.879(2) 1 calc R . P A 1
C3 C 0.0666(2) 0.2640(4) 0.34432(14) 0.0142(5) Uani 0.879(2) 1 d D . P A 1
H3 H 0.014059 0.207173 0.344827 0.017 Uiso 0.879(2) 1 calc R . P A 1
C4 C 0.05963(13) 0.4070(3) 0.29214(10) 0.0140(4) Uani 0.879(2) 1 d D . P A 1
C5 C 0.14401(14) 0.1684(3) 0.27206(11) 0.0119(4) Uani 0.879(2) 1 d D . P A 1
C6 C 0.12312(13) 0.1065(3) 0.33142(10) 0.0138(4) Uani 0.879(2) 1 d D . P A 1
H6 H 0.097192 -0.023777 0.326625 0.017 Uiso 0.879(2) 1 calc R . P A 1
C7 C 0.19243(16) 0.1137(5) 0.39113(13) 0.0179(5) Uani 0.879(2) 1 d D . P A 1
H7 H 0.228165 -0.001642 0.398626 0.021 Uiso 0.879(2) 1 calc R . P A 1
C8 C 0.23183(14) 0.3100(4) 0.39122(11) 0.0189(5) Uani 0.879(2) 1 d D . P A 1
H8 H 0.282731 0.332377 0.384262 0.023 Uiso 0.879(2) 1 calc R . P A 1
C9 C 0.18274(16) 0.4454(5) 0.40272(13) 0.0210(6) Uani 0.879(2) 1 d D . P A 1
H9 H 0.192421 0.581109 0.405753 0.025 Uiso 0.879(2) 1 calc R . P A 1
O1B O 0.1839(8) 0.421(2) 0.2453(6) 0.026(3) Uiso 0.121(2) 1 d D . P A 2
O2B O 0.0203(8) -0.0568(19) 0.2806(7) 0.030(3) Uiso 0.121(2) 1 d D . P A 2
N1B N 0.1066(9) 0.1594(17) 0.2535(6) 0.0118(4) Uani 0.121(2) 1 d D . P A 2
C1B C 0.1406(13) 0.337(3) 0.4375(9) 0.037(5) Uiso 0.121(2) 1 d D . P A 2
H1BA H 0.173665 0.319392 0.480052 0.044 Uiso 0.121(2) 1 calc R . P A 2
H1BB H 0.098760 0.433549 0.437690 0.044 Uiso 0.121(2) 1 calc R . P A 2
C2B C 0.1898(10) 0.386(3) 0.3895(7) 0.017(5) Uiso 0.121(2) 1 d D . P A 2
H2B H 0.224425 0.503316 0.397920 0.020 Uiso 0.121(2) 1 calc R . P A 2
C3B C 0.1195(9) 0.392(2) 0.3313(6) 0.023(4) Uiso 0.121(2) 1 d D . P A 2
H3BA H 0.092892 0.521487 0.327071 0.028 Uiso 0.121(2) 1 calc R . P A 2
C4B C 0.1412(12) 0.335(2) 0.2722(8) 0.021(4) Uiso 0.121(2) 1 d D . P A 2
C5B C 0.0592(10) 0.088(2) 0.2905(7) 0.023(4) Uiso 0.121(2) 1 d D . P A 2
C6B C 0.0635(13) 0.231(3) 0.3427(8) 0.0142(5) Uani 0.121(2) 1 d D . P A 2
H6B H 0.010446 0.282521 0.343974 0.017 Uiso 0.121(2) 1 calc R . P A 2
C7B C 0.1079(11) 0.144(3) 0.4070(9) 0.036(5) Uiso 0.121(2) 1 d D . P A 2
H7B H 0.075664 0.064564 0.429635 0.043 Uiso 0.121(2) 1 calc R . P A 2
C8B C 0.1831(14) 0.051(3) 0.3979(14) 0.037(9) Uiso 0.121(2) 1 d D . P A 2
H8B H 0.194755 -0.083773 0.399565 0.045 Uiso 0.121(2) 1 calc R . P A 2
C9B C 0.2297(10) 0.192(3) 0.3870(8) 0.020(4) Uiso 0.121(2) 1 d D . P A 2
H9B H 0.280318 0.174760 0.378988 0.025 Uiso 0.121(2) 1 calc R . P A 2
Cl1 Cl 0.11323(7) 0.78786(14) 0.02549(4) 0.0311(2) Uani 0.879(2) 1 d D . P A 1
O3A O 0.17370(19) 0.7018(5) 0.26064(14) 0.0128(6) Uani 0.4395(11) 1 d D . P A 1
O3C O 0.0383(2) 0.1976(6) 0.12807(16) 0.0223(8) Uani 0.4395(11) 1 d D . P A 1
C10 C 0.11044(12) 0.4455(3) 0.19766(10) 0.0118(4) Uani 0.879(2) 1 d D . P A 1
C11 C 0.14521(13) 0.6285(3) 0.20282(10) 0.0129(4) Uani 0.879(2) 1 d D . P A 1
H11 H 0.168194 0.681851 0.243043 0.015 Uiso 0.4395(11) 1 d R . P A 1
C12 C 0.14649(18) 0.7335(4) 0.14942(12) 0.0168(6) Uani 0.879(2) 1 d D . P A 1
H12 H 0.169958 0.858543 0.152274 0.020 Uiso 0.879(2) 1 calc R . P A 1
C13 C 0.11305(14) 0.6529(4) 0.09212(11) 0.0173(5) Uani 0.879(2) 1 d D . P A 1
C14 C 0.07844(14) 0.4707(4) 0.08612(11) 0.0176(5) Uani 0.879(2) 1 d D . P A 1
H14 H 0.056261 0.418090 0.046182 0.021 Uiso 0.879(2) 1 calc R . P A 1
C15 C 0.07671(15) 0.3660(3) 0.13956(11) 0.0151(5) Uani 0.879(2) 1 d D . P A 1
H15 H 0.052454 0.240296 0.136475 0.018 Uiso 0.4395(11) 1 d R . P A 1
Cl1B Cl 0.1240(6) -0.2664(12) 0.0303(4) 0.0311(2) Uani 0.121(2) 1 d D . P A 2
O3B O 0.1763(12) -0.194(3) 0.2593(7) 0.018(5) Uiso 0.0726(13) 1 d D . P A 2
O3D O 0.038(2) 0.313(4) 0.1325(14) 0.019(7) Uiso 0.0484(9) 1 d D . P A 2
C10B C 0.1106(8) 0.0580(19) 0.1982(5) 0.021(4) Uiso 0.121(2) 1 d D . P A 2
C11B C 0.1465(9) -0.121(2) 0.2024(6) 0.022(4) Uiso 0.121(2) 1 d D . P A 2
H11B H 0.168783 -0.175735 0.242555 0.027 Uiso 0.0484(9) 1 d R . P A 2
C12B C 0.1506(11) -0.223(3) 0.1497(7) 0.0168(6) Uani 0.121(2) 1 d D . P A 2
H12B H 0.175093 -0.346110 0.151355 0.020 Uiso 0.121(2) 1 calc R . P A 2
C13B C 0.1165(9) -0.133(2) 0.0942(6) 0.029(4) Uiso 0.121(2) 1 d D . P A 2
C14B C 0.0799(9) 0.046(2) 0.0879(7) 0.027(4) Uiso 0.121(2) 1 d D . P A 2
H14B H 0.057550 0.100051 0.048175 0.032 Uiso 0.121(2) 1 calc R . P A 2
C15B C 0.0771(9) 0.144(2) 0.1422(7) 0.027(5) Uiso 0.121(2) 1 d D . P A 2
H15B H 0.052643 0.269482 0.140587 0.033 Uiso 0.0726(13) 1 d R . P A 2
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
O1 0.0229(9) 0.0199(9) 0.0225(9) 0.0048(7) 0.0082(7) 0.0111(7)
O2 0.0198(8) 0.0100(8) 0.0207(8) -0.0019(6) 0.0067(6) 0.0024(6)
N1 0.0120(9) 0.0096(9) 0.0139(9) 0.0002(7) 0.0031(8) 0.0001(7)
C1 0.0192(11) 0.0251(13) 0.0161(11) 0.0043(10) 0.0026(9) -0.0004(10)
C2 0.0175(11) 0.0212(12) 0.0157(11) -0.0025(9) 0.0035(10) 0.0006(10)
C3 0.0135(9) 0.0135(14) 0.0154(9) -0.0001(9) 0.0028(7) -0.0012(9)
C4 0.0121(10) 0.0154(11) 0.0146(10) 0.0000(9) 0.0030(8) -0.0001(9)
C5 0.0113(10) 0.0075(10) 0.0153(10) -0.0016(8) -0.0003(8) -0.0028(8)
C6 0.0144(10) 0.0108(10) 0.0155(10) 0.0011(8) 0.0017(8) -0.0007(8)
C7 0.0164(12) 0.0186(14) 0.0169(12) 0.0039(11) 0.0006(9) 0.0030(12)
C8 0.0143(11) 0.0213(14) 0.0193(11) 0.0005(10) 0.0004(9) -0.0039(10)
C9 0.0224(13) 0.0199(14) 0.0193(12) -0.0054(12) 0.0021(10) -0.0048(11)
N1B 0.0120(9) 0.0096(9) 0.0139(9) 0.0002(7) 0.0031(8) 0.0001(7)
C6B 0.0135(9) 0.0135(14) 0.0154(9) -0.0001(9) 0.0028(7) -0.0012(9)
Cl1 0.0513(5) 0.0242(5) 0.0178(3) 0.0085(4) 0.0079(3) -0.0028(4)
O3A 0.0162(16) 0.0079(17) 0.0142(15) 0.0000(12) 0.0031(12) -0.0029(13)
O3C 0.033(2) 0.0163(19) 0.0178(17) -0.0034(14) 0.0055(15) -0.0134(17)
C10 0.0117(10) 0.0091(10) 0.0151(10) 0.0008(8) 0.0041(8) 0.0014(8)
C11 0.0121(10) 0.0106(10) 0.0157(10) -0.0018(8) 0.0027(8) 0.0010(8)
C12 0.0192(11) 0.0111(14) 0.0214(10) 0.0004(9) 0.0072(8) -0.0011(10)
C13 0.0219(12) 0.0159(11) 0.0155(11) 0.0041(9) 0.0073(9) 0.0022(9)
C14 0.0178(11) 0.0193(12) 0.0150(10) -0.0024(9) 0.0025(8) -0.0006(9)
C15 0.0137(11) 0.0131(11) 0.0193(11) -0.0029(9) 0.0054(9) -0.0020(9)
Cl1B 0.0513(5) 0.0242(5) 0.0178(3) 0.0085(4) 0.0079(3) -0.0028(4)
C12B 0.0192(11) 0.0111(14) 0.0214(10) 0.0004(9) 0.0072(8) -0.0011(10)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.212(3) . ?
O2 C5 1.211(3) . ?
N1 C4 1.390(3) . ?
N1 C5 1.392(3) . ?
N1 C10 1.431(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.540(4) . ?
C1 C7 1.550(4) . ?
C2 H2 1.0000 . ?
C2 C3 1.567(4) . ?
C2 C9 1.516(4) . ?
C3 H3 1.0000 . ?
C3 C4 1.502(4) . ?
C3 C6 1.539(4) . ?
C5 C6 1.506(3) . ?
C6 H6 1.0000 . ?
C6 C7 1.570(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.518(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.332(4) . ?
C9 H9 0.9500 . ?
O1B C4B 1.212(12) . ?
O2B C5B 1.198(12) . ?
N1B C4B 1.372(13) . ?
N1B C5B 1.386(12) . ?
N1B C10B 1.424(9) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
C1B C2B 1.552(14) . ?
C1B C7B 1.541(14) . ?
C2B H2B 1.0000 . ?
C2B C3B 1.559(14) . ?
C2B C9B 1.512(14) . ?
C3B H3BA 1.0000 . ?
C3B C4B 1.498(13) . ?
C3B C6B 1.540(14) . ?
C5B C6B 1.505(14) . ?
C6B H6B 1.0000 . ?
C6B C7B 1.571(15) . ?
C7B H7B 1.0000 . ?
C7B C8B 1.515(15) . ?
C8B H8B 0.9500 . ?
C8B C9B 1.327(14) . ?
C9B H9B 0.9500 . ?
Cl1 C13 1.744(2) . ?
O3A C11 1.357(3) . ?
O3A H11 0.4029 . ?
O3C C15 1.335(4) . ?
O3C H15 0.4006 . ?
C10 C11 1.393(3) . ?
C10 C15 1.395(3) . ?
C11 H11 0.9599 . ?
C11 C12 1.391(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(3) . ?
C13 C14 1.387(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.392(3) . ?
C15 H15 0.9600 . ?
Cl1B C13B 1.719(12) . ?
O3B C11B 1.343(13) . ?
O3B H11B 0.3849 . ?
O3D C15B 1.338(8) . ?
O3D H15B 0.4050 . ?
C10B C11B 1.378(13) . ?
C10B C15B 1.376(13) . ?
C11B H11B 0.9598 . ?
C11B C12B 1.377(13) . ?
C12B H12B 0.9500 . ?
C12B C13B 1.379(14) . ?
C13B C14B 1.381(13) . ?
C14B H14B 0.9500 . ?
C14B C15B 1.388(13) . ?
C15B H15B 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
C4 N1 C5 113.00(19) . . ?
C4 N1 C10 122.30(19) . . ?
C5 N1 C10 124.62(18) . . ?
H1A C1 H1B 110.3 . . ?
C2 C1 H1A 112.9 . . ?
C2 C1 H1B 112.9 . . ?
C2 C1 C7 94.1(2) . . ?
C7 C1 H1A 112.9 . . ?
C7 C1 H1B 112.9 . . ?
C1 C2 H2 116.2 . . ?
C1 C2 C3 98.7(2) . . ?
C3 C2 H2 116.2 . . ?
C9 C2 C1 100.5(2) . . ?
C9 C2 H2 116.2 . . ?
C9 C2 C3 106.7(2) . . ?
C2 C3 H3 110.9 . . ?
C4 C3 C2 114.9(2) . . ?
C4 C3 H3 110.9 . . ?
C4 C3 C6 105.1(2) . . ?
C6 C3 C2 103.7(2) . . ?
C6 C3 H3 110.9 . . ?
O1 C4 N1 123.4(2) . . ?
O1 C4 C3 128.1(2) . . ?
N1 C4 C3 108.6(2) . . ?
O2 C5 N1 123.6(2) . . ?
O2 C5 C6 128.1(2) . . ?
N1 C5 C6 108.31(19) . . ?
C3 C6 H6 111.0 . . ?
C3 C6 C7 102.9(2) . . ?
C5 C6 C3 105.0(2) . . ?
C5 C6 H6 111.0 . . ?
C5 C6 C7 115.4(2) . . ?
C7 C6 H6 111.0 . . ?
C1 C7 C6 98.58(19) . . ?
C1 C7 H7 116.3 . . ?
C6 C7 H7 116.3 . . ?
C8 C7 C1 100.0(2) . . ?
C8 C7 C6 106.8(2) . . ?
C8 C7 H7 116.3 . . ?
C7 C8 H8 125.9 . . ?
C9 C8 C7 108.2(2) . . ?
C9 C8 H8 125.9 . . ?
C2 C9 H9 126.3 . . ?
C8 C9 C2 107.5(2) . . ?
C8 C9 H9 126.3 . . ?
C4B N1B C5B 114.5(10) . . ?
C4B N1B C10B 125.8(11) . . ?
C5B N1B C10B 119.4(11) . . ?
H1BA C1B H1BB 110.1 . . ?
C2B C1B H1BA 112.6 . . ?
C2B C1B H1BB 112.6 . . ?
C7B C1B H1BA 112.6 . . ?
C7B C1B H1BB 112.6 . . ?
C7B C1B C2B 95.5(11) . . ?
C1B C2B H2B 117.2 . . ?
C1B C2B C3B 96.6(12) . . ?
C3B C2B H2B 117.2 . . ?
C9B C2B C1B 99.6(12) . . ?
C9B C2B H2B 117.2 . . ?
C9B C2B C3B 105.9(13) . . ?
C2B C3B H3BA 111.1 . . ?
C4B C3B C2B 113.8(14) . . ?
C4B C3B H3BA 111.1 . . ?
C4B C3B C6B 104.7(12) . . ?
C6B C3B C2B 104.7(12) . . ?
C6B C3B H3BA 111.1 . . ?
O1B C4B N1B 124.0(13) . . ?
O1B C4B C3B 127.7(13) . . ?
N1B C4B C3B 108.2(10) . . ?
O2B C5B N1B 125.4(14) . . ?
O2B C5B C6B 127.5(14) . . ?
N1B C5B C6B 107.1(11) . . ?
C3B C6B H6B 112.0 . . ?
C3B C6B C7B 103.1(13) . . ?
C5B C6B C3B 105.4(13) . . ?
C5B C6B H6B 112.0 . . ?
C5B C6B C7B 111.8(16) . . ?
C7B C6B H6B 112.0 . . ?
C1B C7B C6B 96.9(13) . . ?
C1B C7B H7B 116.5 . . ?
C6B C7B H7B 116.5 . . ?
C8B C7B C1B 100.3(14) . . ?
C8B C7B C6B 107.4(16) . . ?
C8B C7B H7B 116.5 . . ?
C7B C8B H8B 126.2 . . ?
C9B C8B C7B 107.6(14) . . ?
C9B C8B H8B 126.2 . . ?
C2B C9B H9B 125.2 . . ?
C8B C9B C2B 109.5(14) . . ?
C8B C9B H9B 125.2 . . ?
C11 C10 N1 118.9(2) . . ?
C11 C10 C15 120.9(2) . . ?
C15 C10 N1 120.2(2) . . ?
O3A C11 C10 118.1(2) . . ?
O3A C11 C12 122.2(2) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.7(2) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 118.9(2) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 Cl1 118.52(19) . . ?
C12 C13 C14 122.2(2) . . ?
C14 C13 Cl1 119.29(19) . . ?
C13 C14 H14 120.5 . . ?
C13 C14 C15 118.9(2) . . ?
C15 C14 H14 120.5 . . ?
O3C C15 C10 127.0(3) . . ?
O3C C15 C14 113.5(2) . . ?
C10 C15 H15 120.3 . . ?
C14 C15 C10 119.4(2) . . ?
C14 C15 H15 120.3 . . ?
C11B C10B N1B 119.6(12) . . ?
C15B C10B N1B 117.8(12) . . ?
C15B C10B C11B 122.6(11) . . ?
O3B C11B C10B 118.0(15) . . ?
O3B C11B C12B 121.2(15) . . ?
C10B C11B H11B 119.5 . . ?
C12B C11B C10B 120.7(13) . . ?
C12B C11B H11B 119.7 . . ?
C11B C12B H12B 122.3 . . ?
C11B C12B C13B 115.4(15) . . ?
C13B C12B H12B 122.3 . . ?
C12B C13B Cl1B 113.0(11) . . ?
C12B C13B C14B 125.8(13) . . ?
C14B C13B Cl1B 121.2(11) . . ?
C13B C14B H14B 121.4 . . ?
C13B C14B C15B 117.1(13) . . ?
C15B C14B H14B 121.4 . . ?
O3D C15B C10B 127.8(17) . . ?
O3D C15B C14B 113.8(17) . . ?
C10B C15B C14B 118.4(13) . . ?
C10B C15B H15B 120.8 . . ?
C14B C15B H15B 120.8 . . ?
_shelx_res_file
;
TITL ECV1_125_A in I2/a #15
ecv1_125_a.res
created by SHELXL-2016/6 at 16:00:33 on 22-Feb-2017
REM reset to I2/a #15
CELL 0.71073 17.4699 6.8917 22.13692 90 103.57 90
ZERR 8 0.0012 0.0005 0.002 0 0.0016 0
LATT 2
SYMM 0.5-X,+Y,-Z
SFAC C H Cl N O
UNIT 120 96 8 8 24
SADI 0.01 N1B C10B N1 C10
SADI 0.01 O3A C11 O3C C15 O3D C15B O3C C11B
FLAT 0.01 C12B C13B C14B C15B C10B C11B
EADP C3 C6B
EADP C12 C12B
EADP Cl1 Cl1B
EADP N1 N1B
L.S. 7
PLAN 9
SIZE 0.06 0.22 0.28
TEMP -173.15
BOND $H
fmap 2
acta 55.45
REM
REM
REM
WGHT 0.027700 7.646500
EXTI 0.001266
FVAR 0.08778 0.87902
PART 1
O1 5 0.020644 0.554211 0.283153 21.00000 0.02290 0.01987 =
0.02253 0.00483 0.00824 0.01110
O2 5 0.185284 0.084824 0.243486 21.00000 0.01976 0.01000 =
0.02066 -0.00193 0.00672 0.00237
N1 4 0.106223 0.343535 0.253091 21.00000 0.01198 0.00963 =
0.01394 0.00021 0.00312 0.00013
C1 1 0.143431 0.151316 0.439948 21.00000 0.01918 0.02512 =
0.01614 0.00431 0.00260 -0.00045
AFIX 23
H1A 2 0.102908 0.050674 0.439649 21.00000 -1.20000
H1B 2 0.176506 0.168578 0.482505 21.00000 -1.20000
AFIX 0
C2 1 0.108567 0.343338 0.410083 21.00000 0.01748 0.02116 =
0.01574 -0.00250 0.00352 0.00059
AFIX 13
H2 2 0.074674 0.416855 0.432802 21.00000 -1.20000
AFIX 0
C3 1 0.066579 0.263957 0.344316 21.00000 0.01351 0.01346 =
0.01541 -0.00013 0.00282 -0.00124
AFIX 13
H3 2 0.014059 0.207173 0.344827 21.00000 -1.20000
AFIX 0
C4 1 0.059629 0.407035 0.292142 21.00000 0.01209 0.01535 =
0.01463 0.00001 0.00302 -0.00006
C5 1 0.144014 0.168429 0.272063 21.00000 0.01126 0.00753 =
0.01527 -0.00156 -0.00032 -0.00281
C6 1 0.123125 0.106496 0.331423 21.00000 0.01439 0.01077 =
0.01549 0.00112 0.00169 -0.00067
AFIX 13
H6 2 0.097192 -0.023777 0.326625 21.00000 -1.20000
AFIX 0
C7 1 0.192432 0.113655 0.391132 21.00000 0.01642 0.01861 =
0.01692 0.00386 0.00064 0.00300
AFIX 13
H7 2 0.228165 -0.001642 0.398626 21.00000 -1.20000
AFIX 0
C8 1 0.231831 0.309964 0.391215 21.00000 0.01433 0.02129 =
0.01930 0.00045 0.00037 -0.00391
AFIX 43
H8 2 0.282731 0.332377 0.384262 21.00000 -1.20000
AFIX 0
C9 1 0.182740 0.445401 0.402718 21.00000 0.02236 0.01993 =
0.01933 -0.00541 0.00209 -0.00482
AFIX 43
H9 2 0.192421 0.581109 0.405753 21.00000 -1.20000
AFIX 0
SAME 0.015 0.04 O1 > C9
PART 0
PART 2
O1B 5 0.183888 0.420623 0.245303 -21.00000 0.02644
O2B 5 0.020307 -0.056833 0.280639 -21.00000 0.02979
N1B 4 0.106624 0.159367 0.253453 -21.00000 0.01198 0.00963 =
0.01394 0.00021 0.00312 0.00013
C1B 1 0.140639 0.336940 0.437491 -21.00000 0.03661
AFIX 23
H1BA 2 0.173665 0.319392 0.480052 -21.00000 -1.20000
H1BB 2 0.098760 0.433549 0.437690 -21.00000 -1.20000
AFIX 0
C2B 1 0.189847 0.386038 0.389535 -21.00000 0.01652
AFIX 13
H2B 2 0.224425 0.503316 0.397920 -21.00000 -1.20000
AFIX 0
C3B 1 0.119499 0.392062 0.331313 -21.00000 0.02347
AFIX 13
H3BA 2 0.092892 0.521487 0.327071 -21.00000 -1.20000
AFIX 0
C4B 1 0.141215 0.334816 0.272224 -21.00000 0.02061
C5B 1 0.059179 0.088052 0.290508 -21.00000 0.02274
C6B 1 0.063506 0.230682 0.342693 -21.00000 0.01351 0.01346 =
0.01541 -0.00013 0.00282 -0.00124
AFIX 13
H6B 2 0.010446 0.282521 0.343974 -21.00000 -1.20000
AFIX 0
C7B 1 0.107948 0.143660 0.406961 -21.00000 0.03582
AFIX 13
H7B 2 0.075664 0.064564 0.429635 -21.00000 -1.20000
AFIX 0
C8B 1 0.183109 0.051047 0.397851 -21.00000 0.03729
AFIX 43
H8B 2 0.194755 -0.083773 0.399565 -21.00000 -1.20000
AFIX 0
C9B 1 0.229706 0.192447 0.387046 -21.00000 0.02043
AFIX 43
H9B 2 0.280318 0.174760 0.378988 -21.00000 -1.20000
AFIX 0
PART 0
PART 1
CL1 3 0.113230 0.787860 0.025485 21.00000 0.05131 0.02422 =
0.01776 0.00849 0.00793 -0.00277
O3A 5 0.173702 0.701793 0.260641 20.50000 0.01616 0.00791 =
0.01419 0.00001 0.00310 -0.00293
O3C 5 0.038344 0.197584 0.128074 20.50000 0.03267 0.01632 =
0.01776 -0.00342 0.00554 -0.01340
C10 1 0.110445 0.445475 0.197658 21.00000 0.01172 0.00907 =
0.01506 0.00077 0.00414 0.00137
C11 1 0.145214 0.628501 0.202823 21.00000 0.01210 0.01058 =
0.01574 -0.00184 0.00270 0.00095
AFIX 3
H11 2 0.168194 0.681851 0.243043 20.50000 -1.20000
AFIX 0
C12 1 0.146491 0.733503 0.149423 21.00000 0.01921 0.01107 =
0.02143 0.00042 0.00717 -0.00113
AFIX 43
H12 2 0.169958 0.858543 0.152274 21.00000 -1.20000
AFIX 0
C13 1 0.113047 0.652918 0.092122 21.00000 0.02193 0.01588 =
0.01555 0.00408 0.00734 0.00222
C14 1 0.078438 0.470672 0.086125 21.00000 0.01780 0.01931 =
0.01501 -0.00240 0.00253 -0.00063
AFIX 43
H14 2 0.056261 0.418090 0.046182 21.00000 -1.20000
AFIX 0
C15 1 0.076714 0.366026 0.139565 21.00000 0.01375 0.01310 =
0.01928 -0.00291 0.00538 -0.00199
AFIX 3
H15 2 0.052454 0.240296 0.136475 20.50000 -1.20000
AFIX 0
SAME 0.015 0.04 Cl1 > C15
PART 0
PART 2
CL1B 3 0.124022 -0.266366 0.030334 -21.00000 0.05131 0.02422 =
0.01776 0.00849 0.00793 -0.00277
O3B 5 0.176325 -0.194266 0.259301 -20.60000 0.01823
O3D 5 0.038407 0.313211 0.132463 -20.40000 0.01861
C10B 1 0.110602 0.058023 0.198204 -21.00000 0.02078
C11B 1 0.146523 -0.121065 0.202395 -21.00000 0.02215
AFIX 3
H11B 2 0.168783 -0.175735 0.242555 -20.40000 -1.20000
AFIX 0
C12B 1 0.150553 -0.222574 0.149668 -21.00000 0.01921 0.01107 =
0.02143 0.00042 0.00717 -0.00113
AFIX 43
H12B 2 0.175093 -0.346110 0.151355 -21.00000 -1.20000
AFIX 0
C13B 1 0.116515 -0.132579 0.094233 -21.00000 0.02940
C14B 1 0.079890 0.046333 0.087925 -21.00000 0.02699
AFIX 43
H14B 2 0.057550 0.100051 0.048175 -21.00000 -1.20000
AFIX 0
C15B 1 0.077123 0.144292 0.142157 -21.00000 0.02749
AFIX 3
H15B 2 0.052643 0.269482 0.140587 -20.60000 -1.20000
AFIX 0
HKLF 4
REM ECV1_125_A in I2/a #15
REM R1 = 0.0524 for 2832 Fo > 4sig(Fo) and 0.0557 for all 3036 data
REM 272 parameters refined using 64 restraints
END
WGHT 0.0250 7.7187
REM Highest difference peak 0.350, deepest hole -0.291, 1-sigma level 0.062
Q1 1 0.0261 0.1530 0.1630 11.00000 0.05 0.35
Q2 1 0.1393 0.1445 0.3073 11.00000 0.05 0.34
Q3 1 0.1211 -0.2940 0.0618 11.00000 0.05 0.29
Q4 1 0.1399 0.3961 0.4049 11.00000 0.05 0.29
Q5 1 0.1090 0.5456 0.0904 11.00000 0.05 0.28
Q6 1 0.1586 0.1121 0.3579 11.00000 0.05 0.27
Q7 1 0.0878 0.3108 0.3794 11.00000 0.05 0.27
Q8 1 0.1207 0.5433 0.2005 11.00000 0.05 0.26
Q9 1 0.1206 -0.2797 -0.0017 11.00000 0.05 0.26
;
_shelx_res_checksum 37862
_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_ecv1_130
_database_code_depnum_ccdc_archive 'CCDC 2003346'
loop_
_audit_author_name
_audit_author_address
'Mark D. Smith'
;university of south carolina
United States of America
;
_audit_update_record
;
2020-05-11 deposited with the CCDC. 2020-07-02 downloaded from the CCDC.
;
_audit_creation_date 2017-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number 2017/1
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C16 H14 Cl N O3'
_chemical_formula_sum 'C16 H14 Cl N O3'
_chemical_formula_weight 303.73
_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 0.0033 0.0016 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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 9.8726(5)
_cell_length_b 10.9075(5)
_cell_length_c 12.7229(6)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 1370.07(11)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 9800
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 30.04
_cell_measurement_theta_min 2.46
_shelx_estimated_absorpt_T_max 0.918
_shelx_estimated_absorpt_T_min 0.874
_exptl_absorpt_coefficient_mu 0.288
_exptl_absorpt_correction_T_max 0.8622
_exptl_absorpt_correction_T_min 0.8275
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1279 before and 0.0557 after correction.
The Ratio of minimum to maximum transmission is 0.9598.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.473
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description irregular
_exptl_crystal_F_000 632
_exptl_crystal_size_max 0.48
_exptl_crystal_size_mid 0.42
_exptl_crystal_size_min 0.3
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0391
_diffrn_reflns_av_unetI/netI 0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_number 49019
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full 30.084
_diffrn_reflns_theta_max 30.084
_diffrn_reflns_theta_min 2.460
_diffrn_ambient_temperature 100(2)
_diffrn_detector 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type 'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device 'three-circle diffractometer'
_diffrn_measurement_device_type 'Bruker D8 QUEST'
_diffrn_measurement_method '\w and \f scans'
_diffrn_radiation_monochromator 'mirror optics'
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'microfocus sealed X-ray tube'
_diffrn_source_type 'Incoatec I\ms'
_diffrn_special_details ?
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.758
_reflns_Friedel_fraction_full 0.999
_reflns_Friedel_fraction_max 0.999
_reflns_number_gt 3781
_reflns_number_total 4021
_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 'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection 'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction 'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution 'XT (Sheldrick, 2015)'
_refine_diff_density_max 0.257
_refine_diff_density_min -0.204
_refine_diff_density_rms 0.044
_refine_ls_abs_structure_details
;
Flack x determined using 1569 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack 0.013(13)
_refine_ls_extinction_coef 0.0196(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method 'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref 1.029
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 192
_refine_ls_number_reflns 4021
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0309
_refine_ls_R_factor_gt 0.0272
_refine_ls_restrained_S_all 1.029
_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/[\s^2^(Fo^2^)+(0.0303P)^2^+0.4545P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0636
_refine_ls_wR_factor_ref 0.0655
_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 Ternary CH refined with riding coordinates:
C2(H2), C3(H3), C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
C8(H8), C9(H9), C12(H12), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
C16(H16A,H16B,H16C)
;
_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
Cl1 Cl 0.69350(4) 0.80289(4) 0.80188(3) 0.01829(10) Uani 1 1 d . . . . .
O1 O 0.21116(12) 0.49848(11) 0.52796(10) 0.0193(3) Uani 1 1 d . . . . .
O2 O 0.63149(13) 0.48062(12) 0.37982(11) 0.0220(3) Uani 1 1 d . . . . .
O3 O 0.41046(14) 0.74926(11) 0.46795(10) 0.0172(3) Uani 1 1 d . . . . .
N1 N 0.43246(14) 0.50518(12) 0.47118(11) 0.0136(3) Uani 1 1 d . . . . .
C1 C 0.28625(19) 0.24816(17) 0.24412(14) 0.0216(4) Uani 1 1 d . . . . .
H1A H 0.271536 0.160495 0.227520 0.026 Uiso 1 1 calc R . . . .
H1B H 0.255352 0.300300 0.185113 0.026 Uiso 1 1 calc R . . . .
C2 C 0.22447(18) 0.28632(16) 0.35078(14) 0.0185(3) Uani 1 1 d . . . . .
H2 H 0.124725 0.273254 0.358606 0.022 Uiso 1 1 calc R . . . .
C3 C 0.27342(17) 0.42265(15) 0.35316(13) 0.0160(3) Uani 1 1 d . . . . .
H3 H 0.212216 0.475391 0.309830 0.019 Uiso 1 1 calc R . . . .
C4 C 0.29462(17) 0.47866(14) 0.46059(13) 0.0144(3) Uani 1 1 d . . . . .
C5 C 0.51002(18) 0.46891(14) 0.38438(13) 0.0154(3) Uani 1 1 d . . . . .
C6 C 0.41551(17) 0.41606(14) 0.30326(14) 0.0158(3) Uani 1 1 d . . . . .
H6 H 0.418772 0.465423 0.237079 0.019 Uiso 1 1 calc R . . . .
C7 C 0.43299(18) 0.27626(15) 0.27848(13) 0.0169(3) Uani 1 1 d . . . . .
H7 H 0.505622 0.254649 0.226921 0.020 Uiso 1 1 calc R . . . .
C8 C 0.43752(18) 0.20927(15) 0.38315(13) 0.0173(3) Uani 1 1 d . . . . .
H8 H 0.514652 0.170673 0.413119 0.021 Uiso 1 1 calc R . . . .
C9 C 0.31412(19) 0.21424(14) 0.42550(13) 0.0176(3) Uani 1 1 d . . . . .
H9 H 0.287203 0.179099 0.490551 0.021 Uiso 1 1 calc R . . . .
C10 C 0.48858(17) 0.57467(15) 0.55574(13) 0.0134(3) Uani 1 1 d . . . . .
C11 C 0.47970(15) 0.70286(16) 0.55041(12) 0.0131(3) Uani 1 1 d . . . . .
C12 C 0.54222(16) 0.77338(14) 0.62806(13) 0.0136(3) Uani 1 1 d . . . . .
H12 H 0.538468 0.860372 0.625782 0.016 Uiso 1 1 calc R . . . .
C13 C 0.60987(16) 0.71358(14) 0.70854(13) 0.0135(3) Uani 1 1 d . . . . .
C14 C 0.61661(17) 0.58722(15) 0.71704(13) 0.0157(3) Uani 1 1 d . . . . .
H14 H 0.661377 0.549012 0.774448 0.019 Uiso 1 1 calc R . . . .
C15 C 0.55511(17) 0.51810(14) 0.63802(13) 0.0155(3) Uani 1 1 d . . . . .
H15 H 0.559048 0.431143 0.640847 0.019 Uiso 1 1 calc R . . . .
C16 C 0.39331(19) 0.87990(15) 0.46383(15) 0.0186(3) Uani 1 1 d . . . . .
H16A H 0.344665 0.902087 0.399439 0.028 Uiso 1 1 calc GR . . . .
H16B H 0.482324 0.919667 0.464123 0.028 Uiso 1 1 calc GR . . . .
H16C H 0.341242 0.907110 0.525121 0.028 Uiso 1 1 calc GR . . . .
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
Cl1 0.02119(19) 0.01818(17) 0.01550(17) -0.00260(15) -0.00530(16) -0.00008(16)
O1 0.0136(6) 0.0193(6) 0.0249(6) -0.0017(5) 0.0017(5) 0.0009(5)
O2 0.0163(6) 0.0241(7) 0.0255(7) -0.0056(5) 0.0052(5) -0.0042(5)
O3 0.0209(6) 0.0140(5) 0.0167(6) 0.0006(4) -0.0062(5) -0.0002(5)
N1 0.0118(6) 0.0119(6) 0.0172(6) -0.0031(5) 0.0008(5) -0.0017(5)
C1 0.0255(9) 0.0188(8) 0.0206(8) -0.0046(6) -0.0062(7) -0.0018(7)
C2 0.0166(8) 0.0162(8) 0.0227(8) -0.0032(6) -0.0047(6) -0.0032(6)
C3 0.0156(8) 0.0137(7) 0.0189(8) 0.0001(6) -0.0041(6) 0.0008(6)
C4 0.0127(7) 0.0102(6) 0.0204(7) 0.0007(5) -0.0020(6) 0.0008(6)
C5 0.0185(8) 0.0104(7) 0.0173(8) 0.0000(6) 0.0025(6) -0.0017(6)
C6 0.0194(8) 0.0136(7) 0.0144(7) 0.0014(6) -0.0007(7) -0.0013(6)
C7 0.0210(8) 0.0151(7) 0.0148(7) -0.0033(6) -0.0005(6) -0.0005(6)
C8 0.0225(8) 0.0111(7) 0.0182(7) -0.0010(6) -0.0036(6) 0.0020(6)
C9 0.0249(8) 0.0102(7) 0.0179(7) 0.0002(6) -0.0019(7) -0.0032(6)
C10 0.0110(7) 0.0131(7) 0.0161(8) -0.0030(6) 0.0014(6) -0.0014(6)
C11 0.0112(7) 0.0144(7) 0.0135(7) 0.0008(6) 0.0009(5) -0.0001(6)
C12 0.0133(7) 0.0120(7) 0.0154(7) 0.0001(5) -0.0001(6) -0.0004(5)
C13 0.0117(6) 0.0156(7) 0.0131(7) -0.0020(6) 0.0001(6) -0.0010(6)
C14 0.0146(8) 0.0160(7) 0.0166(8) 0.0016(6) -0.0009(6) 0.0015(6)
C15 0.0143(7) 0.0114(7) 0.0207(8) 0.0010(6) 0.0015(6) 0.0002(6)
C16 0.0199(8) 0.0129(7) 0.0230(8) 0.0017(6) -0.0060(7) 0.0020(6)
_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
Cl1 C13 1.7439(16) . ?
O1 C4 1.208(2) . ?
O2 C5 1.207(2) . ?
O3 C11 1.351(2) . ?
O3 C16 1.436(2) . ?
N1 C4 1.398(2) . ?
N1 C5 1.401(2) . ?
N1 C10 1.428(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.545(3) . ?
C1 C7 1.544(3) . ?
C2 H2 1.0000 . ?
C2 C3 1.564(2) . ?
C2 C9 1.518(2) . ?
C3 H3 1.0000 . ?
C3 C4 1.512(2) . ?
C3 C6 1.541(2) . ?
C5 C6 1.506(2) . ?
C6 H6 1.0000 . ?
C6 C7 1.567(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.520(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.333(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.403(2) . ?
C10 C15 1.381(2) . ?
C11 C12 1.396(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(2) . ?
C13 C14 1.384(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.396(2) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O3 C16 117.38(14) . . ?
C4 N1 C5 113.44(13) . . ?
C4 N1 C10 124.07(13) . . ?
C5 N1 C10 122.12(14) . . ?
H1A C1 H1B 110.4 . . ?
C2 C1 H1A 112.9 . . ?
C2 C1 H1B 112.9 . . ?
C7 C1 H1A 112.9 . . ?
C7 C1 H1B 112.9 . . ?
C7 C1 C2 93.92(13) . . ?
C1 C2 H2 116.0 . . ?
C1 C2 C3 98.70(14) . . ?
C3 C2 H2 116.0 . . ?
C9 C2 C1 100.39(14) . . ?
C9 C2 H2 116.0 . . ?
C9 C2 C3 107.46(13) . . ?
C2 C3 H3 110.5 . . ?
C4 C3 C2 116.40(14) . . ?
C4 C3 H3 110.5 . . ?
C4 C3 C6 105.38(14) . . ?
C6 C3 C2 103.23(13) . . ?
C6 C3 H3 110.5 . . ?
O1 C4 N1 123.95(15) . . ?
O1 C4 C3 128.26(15) . . ?
N1 C4 C3 107.79(14) . . ?
O2 C5 N1 123.43(16) . . ?
O2 C5 C6 128.53(16) . . ?
N1 C5 C6 108.04(14) . . ?
C3 C6 H6 110.5 . . ?
C3 C6 C7 103.21(13) . . ?
C5 C6 C3 105.29(14) . . ?
C5 C6 H6 110.5 . . ?
C5 C6 C7 116.25(14) . . ?
C7 C6 H6 110.5 . . ?
C1 C7 C6 98.44(14) . . ?
C1 C7 H7 116.1 . . ?
C6 C7 H7 116.1 . . ?
C8 C7 C1 100.38(14) . . ?
C8 C7 C6 107.14(13) . . ?
C8 C7 H7 116.1 . . ?
C7 C8 H8 126.0 . . ?
C9 C8 C7 107.92(15) . . ?
C9 C8 H8 126.0 . . ?
C2 C9 H9 126.3 . . ?
C8 C9 C2 107.50(15) . . ?
C8 C9 H9 126.3 . . ?
C11 C10 N1 117.93(14) . . ?
C15 C10 N1 121.22(14) . . ?
C15 C10 C11 120.78(15) . . ?
O3 C11 C10 116.28(14) . . ?
O3 C11 C12 124.54(15) . . ?
C12 C11 C10 119.17(14) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 C11 118.47(14) . . ?
C13 C12 H12 120.8 . . ?
C12 C13 Cl1 117.93(12) . . ?
C14 C13 Cl1 118.70(13) . . ?
C14 C13 C12 123.35(15) . . ?
C13 C14 H14 121.3 . . ?
C13 C14 C15 117.43(15) . . ?
C15 C14 H14 121.3 . . ?
C10 C15 C14 120.76(15) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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
Cl1 C13 C14 C15 -176.52(12) . . . . ?
O2 C5 C6 C3 178.96(17) . . . . ?
O2 C5 C6 C7 65.4(2) . . . . ?
O3 C11 C12 C13 179.90(15) . . . . ?
N1 C5 C6 C3 -1.22(17) . . . . ?
N1 C5 C6 C7 -114.73(16) . . . . ?
N1 C10 C11 O3 4.1(2) . . . . ?
N1 C10 C11 C12 -175.41(14) . . . . ?
N1 C10 C15 C14 176.14(15) . . . . ?
C1 C2 C3 C4 -151.92(14) . . . . ?
C1 C2 C3 C6 -37.03(15) . . . . ?
C1 C2 C9 C8 33.65(17) . . . . ?
C1 C7 C8 C9 -32.37(17) . . . . ?
C2 C1 C7 C6 -60.06(15) . . . . ?
C2 C1 C7 C8 49.22(14) . . . . ?
C2 C3 C4 O1 -64.6(2) . . . . ?
C2 C3 C4 N1 115.24(15) . . . . ?
C2 C3 C6 C5 -122.78(14) . . . . ?
C2 C3 C6 C7 -0.42(16) . . . . ?
C3 C2 C9 C8 -69.00(17) . . . . ?
C3 C6 C7 C1 37.73(16) . . . . ?
C3 C6 C7 C8 -65.95(17) . . . . ?
C4 N1 C5 O2 -177.79(16) . . . . ?
C4 N1 C5 C6 2.38(18) . . . . ?
C4 N1 C10 C11 -80.4(2) . . . . ?
C4 N1 C10 C15 102.49(19) . . . . ?
C4 C3 C6 C5 -0.20(16) . . . . ?
C4 C3 C6 C7 122.15(14) . . . . ?
C5 N1 C4 O1 177.30(15) . . . . ?
C5 N1 C4 C3 -2.51(18) . . . . ?
C5 N1 C10 C11 92.18(19) . . . . ?
C5 N1 C10 C15 -84.9(2) . . . . ?
C5 C6 C7 C1 152.43(15) . . . . ?
C5 C6 C7 C8 48.75(19) . . . . ?
C6 C3 C4 O1 -178.23(16) . . . . ?
C6 C3 C4 N1 1.56(16) . . . . ?
C6 C7 C8 C9 69.91(17) . . . . ?
C7 C1 C2 C3 59.91(14) . . . . ?
C7 C1 C2 C9 -49.77(15) . . . . ?
C7 C8 C9 C2 -0.79(18) . . . . ?
C9 C2 C3 C4 -48.1(2) . . . . ?
C9 C2 C3 C6 66.83(17) . . . . ?
C10 N1 C4 O1 -9.5(2) . . . . ?
C10 N1 C4 C3 170.67(14) . . . . ?
C10 N1 C5 O2 8.9(3) . . . . ?
C10 N1 C5 C6 -170.95(14) . . . . ?
C10 C11 C12 C13 -0.7(2) . . . . ?
C11 C10 C15 C14 -0.9(2) . . . . ?
C11 C12 C13 Cl1 177.35(12) . . . . ?
C11 C12 C13 C14 -1.2(2) . . . . ?
C12 C13 C14 C15 2.0(3) . . . . ?
C13 C14 C15 C10 -1.0(2) . . . . ?
C15 C10 C11 O3 -178.83(15) . . . . ?
C15 C10 C11 C12 1.7(2) . . . . ?
C16 O3 C11 C10 176.56(15) . . . . ?
C16 O3 C11 C12 -4.0(2) . . . . ?
_shelx_res_file
;
TITL ecv1_130_a.res in P2(1)2(1)2(1)
ecv1_130.res
created by SHELXL-2017/1 at 12:55:44 on 22-Nov-2017
REM Old TITL ECV1_130 in P2(1)2(1)2(1)
REM SHELXT solution in P2(1)2(1)2(1)
REM R1 0.071, Rweak 0.019, Alpha 0.001, Orientation as input
REM Flack x = 0.028 ( 0.012 ) from Parsons' quotients
REM Formula found by SHELXT: C16 N O3 Cl
CELL 0.71073 9.8726 10.9075 12.7229 90 90 90
ZERR 4 0.0005 0.0005 0.0006 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 Cl N O
UNIT 64 56 4 4 12
L.S. 7
PLAN 9
SIZE 0.3 0.42 0.48
TEMP -173(2)
BOND $H
CONF
list 4
fmap 2
acta 60.17
OMIT 0 6 0
REM
REM
REM
WGHT 0.030300 0.454500
EXTI 0.019639
FVAR 0.99921
CL1 3 0.693503 0.802890 0.801882 11.00000 0.02119 0.01818 =
0.01550 -0.00260 -0.00530 -0.00008
O1 5 0.211156 0.498475 0.527961 11.00000 0.01363 0.01928 =
0.02491 -0.00169 0.00174 0.00088
O2 5 0.631488 0.480622 0.379819 11.00000 0.01635 0.02413 =
0.02550 -0.00561 0.00524 -0.00424
O3 5 0.410462 0.749263 0.467950 11.00000 0.02094 0.01397 =
0.01665 0.00061 -0.00620 -0.00017
N1 4 0.432457 0.505183 0.471181 11.00000 0.01181 0.01195 =
0.01717 -0.00314 0.00078 -0.00166
C1 1 0.286245 0.248163 0.244123 11.00000 0.02551 0.01885 =
0.02056 -0.00455 -0.00625 -0.00179
AFIX 23
H1A 2 0.271536 0.160495 0.227520 11.00000 -1.20000
H1B 2 0.255352 0.300300 0.185113 11.00000 -1.20000
AFIX 0
C2 1 0.224472 0.286321 0.350776 11.00000 0.01656 0.01621 =
0.02270 -0.00316 -0.00472 -0.00319
AFIX 13
H2 2 0.124725 0.273254 0.358606 11.00000 -1.20000
AFIX 0
C3 1 0.273417 0.422648 0.353164 11.00000 0.01556 0.01368 =
0.01886 0.00011 -0.00408 0.00085
AFIX 13
H3 2 0.212216 0.475391 0.309830 11.00000 -1.20000
AFIX 0
C4 1 0.294616 0.478664 0.460593 11.00000 0.01274 0.01017 =
0.02039 0.00071 -0.00200 0.00077
C5 1 0.510024 0.468911 0.384379 11.00000 0.01848 0.01042 =
0.01728 0.00001 0.00250 -0.00172
C6 1 0.415511 0.416061 0.303263 11.00000 0.01938 0.01356 =
0.01445 0.00138 -0.00066 -0.00134
AFIX 13
H6 2 0.418772 0.465423 0.237079 11.00000 -1.20000
AFIX 0
C7 1 0.432988 0.276257 0.278476 11.00000 0.02096 0.01505 =
0.01482 -0.00330 -0.00053 -0.00049
AFIX 13
H7 2 0.505622 0.254649 0.226921 11.00000 -1.20000
AFIX 0
C8 1 0.437517 0.209270 0.383154 11.00000 0.02248 0.01107 =
0.01820 -0.00100 -0.00358 0.00196
AFIX 43
H8 2 0.514652 0.170673 0.413119 11.00000 -1.20000
AFIX 0
C9 1 0.314124 0.214239 0.425502 11.00000 0.02487 0.01020 =
0.01787 0.00021 -0.00193 -0.00322
AFIX 43
H9 2 0.287203 0.179099 0.490551 11.00000 -1.20000
AFIX 0
C10 1 0.488579 0.574674 0.555741 11.00000 0.01105 0.01308 =
0.01610 -0.00296 0.00143 -0.00135
C11 1 0.479703 0.702858 0.550407 11.00000 0.01123 0.01441 =
0.01352 0.00081 0.00086 -0.00014
C12 1 0.542220 0.773383 0.628060 11.00000 0.01330 0.01197 =
0.01544 0.00006 -0.00006 -0.00045
AFIX 43
H12 2 0.538468 0.860372 0.625782 11.00000 -1.20000
AFIX 0
C13 1 0.609873 0.713576 0.708537 11.00000 0.01167 0.01560 =
0.01315 -0.00200 0.00007 -0.00097
C14 1 0.616614 0.587220 0.717039 11.00000 0.01464 0.01595 =
0.01658 0.00158 -0.00086 0.00154
AFIX 43
H14 2 0.661377 0.549012 0.774448 11.00000 -1.20000
AFIX 0
C15 1 0.555110 0.518103 0.638017 11.00000 0.01431 0.01136 =
0.02074 0.00102 0.00151 0.00022
AFIX 43
H15 2 0.559048 0.431143 0.640847 11.00000 -1.20000
AFIX 0
C16 1 0.393312 0.879902 0.463832 11.00000 0.01987 0.01292 =
0.02303 0.00167 -0.00604 0.00203
AFIX 137
H16A 2 0.344665 0.902087 0.399439 11.00000 -1.50000
H16B 2 0.482324 0.919667 0.464123 11.00000 -1.50000
H16C 2 0.341242 0.907110 0.525121 11.00000 -1.50000
AFIX 0
HKLF 4
REM ecv1_130_a.res in P2(1)2(1)2(1)
REM R1 = 0.0272 for 3781 Fo > 4sig(Fo) and 0.0309 for all 4021 data
REM 192 parameters refined using 0 restraints
END
WGHT 0.0306 0.4533
REM Highest difference peak 0.257, deepest hole -0.204, 1-sigma level 0.044
Q1 1 0.5893 0.7405 0.6632 11.00000 0.05 0.26
Q2 1 0.4582 0.4377 0.3446 11.00000 0.05 0.25
Q3 1 0.4431 0.2502 0.3358 11.00000 0.05 0.24
Q4 1 0.4308 0.3533 0.2997 11.00000 0.05 0.24
Q5 1 0.5346 0.7374 0.5818 11.00000 0.05 0.24
Q6 1 0.3491 0.4154 0.3385 11.00000 0.05 0.23
Q7 1 0.6020 0.6532 0.7169 11.00000 0.05 0.22
Q8 1 0.2541 0.2567 0.3965 11.00000 0.05 0.22
Q9 1 0.2746 0.4574 0.4022 11.00000 0.05 0.20
;
_shelx_res_checksum 36078
_olex2_submission_special_instructions 'No special instructions were received'