# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016
#######################################################################
#
# 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.
#
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data_cd1394a
_database_code_depnum_ccdc_archive 'CCDC 1457713'
_audit_update_record
;
2016-03-03 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;
_audit_creation_date 2015-12-08
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C24 H23 N'
_chemical_formula_sum 'C24 H23 N'
_chemical_formula_weight 325.43
_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'
_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 8.9502(6)
_cell_length_b 9.1881(5)
_cell_length_c 11.6731(8)
_cell_angle_alpha 83.963(6)
_cell_angle_beta 70.783(5)
_cell_angle_gamma 77.642(5)
_cell_volume 884.82(10)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 5885
_cell_measurement_temperature 98
_cell_measurement_theta_max 27.5
_cell_measurement_theta_min 3.0
_shelx_estimated_absorpt_T_max 0.993
_shelx_estimated_absorpt_T_min 0.966
_exptl_absorpt_coefficient_mu 0.070
_exptl_absorpt_correction_T_max 1.000
_exptl_absorpt_correction_T_min 0.829
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)'
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier .
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.221
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description plate
_exptl_crystal_F_000 348
_exptl_crystal_size_max 0.5
_exptl_crystal_size_mid 0.33
_exptl_crystal_size_min 0.1
_exptl_special_details
;
?
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0195
_diffrn_reflns_av_unetI/netI 0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_number 6971
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 27.485
_diffrn_reflns_theta_min 3.010
_diffrn_ambient_temperature 98
_diffrn_detector CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
scan:
Number of images: 246
Slice: -68.0000 - 55.0000
Image width: 0.5000
Exp time: 35.0000
Rotation axis: Omega
Omega: 0.0000
Kappa: 70.0000
Phi: 270.0000
XTD: 35.0000
2theta: -35.0000
scan:
Number of images: 180
Slice: -80.0000 - 10.0000
Image width: 0.5000
Exp time: 35.0000
Rotation axis: Omega
Omega: 0.0000
Kappa: 0.0000
Phi: 90.0000
XTD: 35.0000
2theta: -35.0000
scan:
Number of images: 122
Slice: -50.0000 - 11.0000
Image width: 0.5000
Exp time: 35.0000
Rotation axis: Omega
Omega: 0.0000
Kappa: 0.0000
Phi: 180.0000
XTD: 35.0000
2theta: -35.0000
scan:
Number of images: 84
Slice: -53.0000 - -11.0000
Image width: 0.5000
Exp time: 35.0000
Rotation axis: Omega
Omega: 0.0000
Kappa: 70.0000
Phi: 90.0000
XTD: 35.0000
2theta: -35.0000
scan:
Number of images: 50
Slice: -35.0000 - -10.0000
Image width: 0.5000
Exp time: 35.0000
Rotation axis: Omega
Omega: 0.0000
Kappa: 70.0000
Phi: 0.0000
XTD: 35.0000
2theta: -35.0000
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type d*Trek
_diffrn_orient_matrix_UB_11 -0.023966
_diffrn_orient_matrix_UB_12 0.053113
_diffrn_orient_matrix_UB_13 0.105065
_diffrn_orient_matrix_UB_21 0.109822
_diffrn_orient_matrix_UB_22 -0.009171
_diffrn_orient_matrix_UB_23 0.005477
_diffrn_orient_matrix_UB_31 0.004983
_diffrn_orient_matrix_UB_32 0.063749
_diffrn_orient_matrix_UB_33 -0.063792
_diffrn_radiation_monochromator 'Graphite Monochromator'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71075
_diffrn_source 'Sealed Tube'
_diffrn_source_current 40.0
_diffrn_source_power 2.0
_diffrn_source_voltage 50.0
_diffrn_special_details
;
?
;
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 3573
_reflns_number_total 4038
_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
;
CrystalClear-SM Auto 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Auto 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Auto 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2008)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.311
_refine_diff_density_min -0.200
_refine_diff_density_rms 0.040
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.039
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 228
_refine_ls_number_reflns 4038
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0462
_refine_ls_R_factor_gt 0.0410
_refine_ls_restrained_S_all 1.039
_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^)+(0.0550P)^2^+0.2930P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1063
_refine_ls_wR_factor_ref 0.1105
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
At 1.5 times of:
All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
C9(H9A,H9B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
C1(H1), C7(H7), C11(H11), C19(H19), C5(H5), C14(H14), C23(H23), C6(H6),
C20(H20), C12(H12), C22(H22), C21(H21), C13(H13)
2.c Idealised Me refined as rotating group:
C24(H24A,H24B,H24C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.53300(11) 0.60607(10) 0.59911(8) 0.0185(2) Uani 1 1 d . . . . .
C3 C 0.55606(12) 0.44664(11) 0.75620(9) 0.0173(2) Uani 1 1 d . . . . .
C2 C 0.39311(12) 0.53077(11) 0.78689(9) 0.0174(2) Uani 1 1 d . . . . .
C10 C 0.65456(12) 0.81456(11) 0.47596(9) 0.0171(2) Uani 1 1 d . . . . .
C18 C 0.09940(12) 0.61932(12) 0.88935(9) 0.0183(2) Uani 1 1 d . . . . .
C1 C 0.38672(13) 0.62485(12) 0.68913(10) 0.0186(2) Uani 1 1 d . . . . .
H1 H 0.2954 0.6926 0.6842 0.022 Uiso 1 1 calc R . . . .
C8 C 0.63935(13) 0.49787(11) 0.63816(10) 0.0180(2) Uani 1 1 d . . . . .
C7 C 0.80100(13) 0.43995(12) 0.57728(10) 0.0209(2) Uani 1 1 d . . . . .
H7 H 0.8533 0.4754 0.5000 0.025 Uiso 1 1 calc R . . . .
C11 C 0.68079(13) 0.85773(12) 0.57703(10) 0.0210(2) Uani 1 1 d . . . . .
H11 H 0.6421 0.8097 0.6520 0.025 Uiso 1 1 calc R . . . .
C4 C 0.63898(13) 0.33102(12) 0.81492(10) 0.0195(2) Uani 1 1 d . . . . .
C15 C 0.70923(13) 0.88978(12) 0.36382(10) 0.0200(2) Uani 1 1 d . . . . .
C19 C 0.01514(13) 0.57620(13) 0.82145(10) 0.0232(2) Uani 1 1 d . . . . .
H19 H 0.0510 0.4836 0.7863 0.028 Uiso 1 1 calc R . . . .
C9 C 0.56766(13) 0.68817(12) 0.48344(9) 0.0192(2) Uani 1 1 d . . . . .
H9A H 0.4669 0.7284 0.4671 0.023 Uiso 1 1 calc R . . . .
H9B H 0.6327 0.6193 0.4203 0.023 Uiso 1 1 calc R . . . .
C17 C 0.25251(12) 0.52070(12) 0.90063(9) 0.0185(2) Uani 1 1 d . . . . .
H17A H 0.2373 0.4182 0.9159 0.022 Uiso 1 1 calc R . . . .
H17B H 0.2761 0.5503 0.9692 0.022 Uiso 1 1 calc R . . . .
C5 C 0.79930(13) 0.27481(12) 0.75356(11) 0.0227(2) Uani 1 1 d . . . . .
H5 H 0.8560 0.1990 0.7911 0.027 Uiso 1 1 calc R . . . .
C14 C 0.79510(14) 1.00185(12) 0.35555(11) 0.0243(2) Uani 1 1 d . . . . .
H14 H 0.8346 1.0501 0.2809 0.029 Uiso 1 1 calc R . . . .
C24 C 0.55572(14) 0.26657(13) 0.93840(10) 0.0229(2) Uani 1 1 d . . . . .
H24A H 0.5080 0.3452 0.9949 0.034 Uiso 1 1 calc GR . . . .
H24B H 0.6331 0.1951 0.9660 0.034 Uiso 1 1 calc GR . . . .
H24C H 0.4732 0.2185 0.9328 0.034 Uiso 1 1 calc GR . . . .
C23 C 0.04177(14) 0.75736(12) 0.94210(10) 0.0229(2) Uani 1 1 d . . . . .
H23 H 0.0952 0.7876 0.9889 0.028 Uiso 1 1 calc R . . . .
C6 C 0.87944(13) 0.32792(12) 0.63691(11) 0.0231(2) Uani 1 1 d . . . . .
H6 H 0.9871 0.2868 0.5993 0.028 Uiso 1 1 calc R . . . .
C20 C -0.12099(14) 0.66879(15) 0.80542(11) 0.0287(3) Uani 1 1 d . . . . .
H20 H -0.1759 0.6382 0.7599 0.034 Uiso 1 1 calc R . . . .
C12 C 0.76424(15) 0.97198(13) 0.56742(11) 0.0267(3) Uani 1 1 d . . . . .
H12 H 0.7806 1.0006 0.6358 0.032 Uiso 1 1 calc R . . . .
C22 C -0.09461(15) 0.85095(13) 0.92599(11) 0.0276(3) Uani 1 1 d . . . . .
H22 H -0.1314 0.9432 0.9616 0.033 Uiso 1 1 calc R . . . .
C21 C -0.17566(14) 0.80742(14) 0.85727(11) 0.0296(3) Uani 1 1 d . . . . .
H21 H -0.2662 0.8705 0.8458 0.036 Uiso 1 1 calc R . . . .
C13 C 0.82296(14) 1.04302(13) 0.45612(12) 0.0271(3) Uani 1 1 d . . . . .
H13 H 0.8809 1.1181 0.4489 0.032 Uiso 1 1 calc R . . . .
C16 C 0.67514(17) 0.85199(14) 0.25384(10) 0.0305(3) Uani 1 1 d . . . . .
H16A H 0.7361 0.7551 0.2279 0.046 Uiso 1 1 calc GR . . . .
H16B H 0.7054 0.9249 0.1897 0.046 Uiso 1 1 calc GR . . . .
H16C H 0.5622 0.8518 0.2738 0.046 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
N1 0.0177(4) 0.0182(4) 0.0193(4) 0.0020(3) -0.0051(3) -0.0055(3)
C3 0.0172(5) 0.0176(5) 0.0191(5) -0.0016(4) -0.0063(4) -0.0062(4)
C2 0.0177(5) 0.0169(5) 0.0186(5) -0.0008(4) -0.0064(4) -0.0046(4)
C10 0.0147(5) 0.0156(5) 0.0192(5) 0.0002(4) -0.0037(4) -0.0019(4)
C18 0.0173(5) 0.0217(5) 0.0139(4) 0.0021(4) -0.0022(4) -0.0052(4)
C1 0.0175(5) 0.0178(5) 0.0202(5) 0.0001(4) -0.0045(4) -0.0053(4)
C8 0.0194(5) 0.0161(5) 0.0207(5) -0.0003(4) -0.0074(4) -0.0065(4)
C7 0.0190(5) 0.0214(5) 0.0224(5) -0.0016(4) -0.0045(4) -0.0071(4)
C11 0.0226(5) 0.0207(5) 0.0212(5) 0.0023(4) -0.0091(4) -0.0050(4)
C4 0.0208(5) 0.0186(5) 0.0223(5) 0.0002(4) -0.0098(4) -0.0065(4)
C15 0.0197(5) 0.0174(5) 0.0189(5) -0.0001(4) -0.0024(4) -0.0011(4)
C19 0.0225(5) 0.0269(6) 0.0204(5) -0.0017(4) -0.0066(4) -0.0048(4)
C9 0.0212(5) 0.0204(5) 0.0165(5) 0.0017(4) -0.0050(4) -0.0077(4)
C17 0.0183(5) 0.0210(5) 0.0163(5) 0.0004(4) -0.0053(4) -0.0046(4)
C5 0.0217(5) 0.0202(5) 0.0283(6) 0.0006(4) -0.0116(4) -0.0032(4)
C14 0.0232(5) 0.0178(5) 0.0265(6) 0.0046(4) -0.0023(4) -0.0039(4)
C24 0.0222(5) 0.0254(5) 0.0223(5) 0.0057(4) -0.0100(4) -0.0057(4)
C23 0.0247(5) 0.0233(5) 0.0190(5) -0.0005(4) -0.0037(4) -0.0062(4)
C6 0.0165(5) 0.0233(5) 0.0289(6) -0.0036(4) -0.0058(4) -0.0035(4)
C20 0.0236(6) 0.0404(7) 0.0234(6) 0.0026(5) -0.0101(5) -0.0066(5)
C12 0.0313(6) 0.0235(6) 0.0321(6) 0.0014(4) -0.0178(5) -0.0084(5)
C22 0.0291(6) 0.0215(5) 0.0229(5) 0.0018(4) 0.0004(5) -0.0005(4)
C21 0.0212(5) 0.0356(7) 0.0237(6) 0.0090(5) -0.0033(4) 0.0014(5)
C13 0.0255(6) 0.0185(5) 0.0403(7) 0.0040(5) -0.0135(5) -0.0083(4)
C16 0.0460(7) 0.0263(6) 0.0173(5) 0.0008(4) -0.0062(5) -0.0098(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
N1 C1 1.3725(13) . ?
N1 C8 1.3738(14) . ?
N1 C9 1.4486(13) . ?
C3 C2 1.4438(14) . ?
C3 C8 1.4190(14) . ?
C3 C4 1.4119(15) . ?
C2 C1 1.3664(15) . ?
C2 C17 1.5096(14) . ?
C10 C11 1.3874(15) . ?
C10 C15 1.4012(14) . ?
C10 C9 1.5106(14) . ?
C18 C19 1.3933(16) . ?
C18 C17 1.5095(14) . ?
C18 C23 1.3889(15) . ?
C1 H1 0.9300 . ?
C8 C7 1.3981(15) . ?
C7 H7 0.9300 . ?
C7 C6 1.3779(16) . ?
C11 H11 0.9300 . ?
C11 C12 1.3885(16) . ?
C4 C5 1.3866(15) . ?
C4 C24 1.5118(15) . ?
C15 C14 1.3889(16) . ?
C15 C16 1.5029(16) . ?
C19 H19 0.9300 . ?
C19 C20 1.3843(16) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C5 H5 0.9300 . ?
C5 C6 1.4050(16) . ?
C14 H14 0.9300 . ?
C14 C13 1.3820(18) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C23 H23 0.9300 . ?
C23 C22 1.3901(17) . ?
C6 H6 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.3887(19) . ?
C12 H12 0.9300 . ?
C12 C13 1.3818(17) . ?
C22 H22 0.9300 . ?
C22 C21 1.3800(19) . ?
C21 H21 0.9300 . ?
C13 H13 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C1 N1 C8 108.36(9) . . ?
C1 N1 C9 125.22(9) . . ?
C8 N1 C9 126.42(9) . . ?
C8 C3 C2 106.61(9) . . ?
C4 C3 C2 134.52(10) . . ?
C4 C3 C8 118.84(9) . . ?
C3 C2 C17 129.24(9) . . ?
C1 C2 C3 106.01(9) . . ?
C1 C2 C17 124.74(10) . . ?
C11 C10 C15 119.56(10) . . ?
C11 C10 C9 121.67(9) . . ?
C15 C10 C9 118.77(9) . . ?
C19 C18 C17 120.55(10) . . ?
C23 C18 C19 118.12(10) . . ?
C23 C18 C17 121.29(10) . . ?
N1 C1 H1 124.5 . . ?
C2 C1 N1 111.02(9) . . ?
C2 C1 H1 124.5 . . ?
N1 C8 C3 108.00(9) . . ?
N1 C8 C7 129.02(10) . . ?
C7 C8 C3 122.97(10) . . ?
C8 C7 H7 121.5 . . ?
C6 C7 C8 117.03(10) . . ?
C6 C7 H7 121.5 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.66(10) . . ?
C12 C11 H11 119.7 . . ?
C3 C4 C24 121.64(10) . . ?
C5 C4 C3 117.56(10) . . ?
C5 C4 C24 120.77(10) . . ?
C10 C15 C16 121.14(10) . . ?
C14 C15 C10 118.89(10) . . ?
C14 C15 C16 119.97(10) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.14(11) . . ?
C20 C19 H19 119.4 . . ?
N1 C9 C10 114.61(9) . . ?
N1 C9 H9A 108.6 . . ?
N1 C9 H9B 108.6 . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C2 C17 H17A 109.3 . . ?
C2 C17 H17B 109.3 . . ?
C18 C17 C2 111.42(9) . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C4 C5 H5 118.7 . . ?
C4 C5 C6 122.55(10) . . ?
C6 C5 H5 118.7 . . ?
C15 C14 H14 119.3 . . ?
C13 C14 C15 121.30(10) . . ?
C13 C14 H14 119.3 . . ?
C4 C24 H24A 109.5 . . ?
C4 C24 H24B 109.5 . . ?
C4 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C18 C23 H23 119.5 . . ?
C18 C23 C22 120.96(11) . . ?
C22 C23 H23 119.5 . . ?
C7 C6 C5 121.05(10) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.02(12) . . ?
C21 C20 H20 120.0 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.88(11) . . ?
C13 C12 H12 120.1 . . ?
C23 C22 H22 119.9 . . ?
C21 C22 C23 120.23(11) . . ?
C21 C22 H22 119.9 . . ?
C20 C21 H21 120.2 . . ?
C22 C21 C20 119.52(11) . . ?
C22 C21 H21 120.2 . . ?
C14 C13 H13 120.2 . . ?
C12 C13 C14 119.64(11) . . ?
C12 C13 H13 120.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 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
N1 C8 C7 C6 -178.26(10) . . . . ?
C3 C2 C1 N1 0.18(12) . . . . ?
C3 C2 C17 C18 -174.39(10) . . . . ?
C3 C8 C7 C6 0.17(16) . . . . ?
C3 C4 C5 C6 -0.37(16) . . . . ?
C2 C3 C8 N1 -0.37(11) . . . . ?
C2 C3 C8 C7 -179.09(9) . . . . ?
C2 C3 C4 C5 178.64(11) . . . . ?
C2 C3 C4 C24 0.61(18) . . . . ?
C10 C11 C12 C13 -0.46(17) . . . . ?
C10 C15 C14 C13 -1.98(16) . . . . ?
C18 C19 C20 C21 0.10(18) . . . . ?
C18 C23 C22 C21 0.28(17) . . . . ?
C1 N1 C8 C3 0.48(12) . . . . ?
C1 N1 C8 C7 179.10(10) . . . . ?
C1 N1 C9 C10 100.29(12) . . . . ?
C1 C2 C17 C18 4.48(15) . . . . ?
C8 N1 C1 C2 -0.42(12) . . . . ?
C8 N1 C9 C10 -79.21(13) . . . . ?
C8 C3 C2 C1 0.11(11) . . . . ?
C8 C3 C2 C17 179.14(10) . . . . ?
C8 C3 C4 C5 0.68(15) . . . . ?
C8 C3 C4 C24 -177.35(9) . . . . ?
C8 C7 C6 C5 0.16(16) . . . . ?
C11 C10 C15 C14 2.87(15) . . . . ?
C11 C10 C15 C16 -176.58(10) . . . . ?
C11 C10 C9 N1 -7.22(14) . . . . ?
C11 C12 C13 C14 1.39(18) . . . . ?
C4 C3 C2 C1 -178.02(11) . . . . ?
C4 C3 C2 C17 1.01(19) . . . . ?
C4 C3 C8 N1 178.12(9) . . . . ?
C4 C3 C8 C7 -0.60(15) . . . . ?
C4 C5 C6 C7 -0.06(17) . . . . ?
C15 C10 C11 C12 -1.69(16) . . . . ?
C15 C10 C9 N1 172.97(9) . . . . ?
C15 C14 C13 C12 -0.15(18) . . . . ?
C19 C18 C17 C2 76.82(12) . . . . ?
C19 C18 C23 C22 -1.03(16) . . . . ?
C19 C20 C21 C22 -0.87(18) . . . . ?
C9 N1 C1 C2 -179.99(9) . . . . ?
C9 N1 C8 C3 -179.95(9) . . . . ?
C9 N1 C8 C7 -1.33(18) . . . . ?
C9 C10 C11 C12 178.50(10) . . . . ?
C9 C10 C15 C14 -177.32(9) . . . . ?
C9 C10 C15 C16 3.24(15) . . . . ?
C17 C2 C1 N1 -178.90(9) . . . . ?
C17 C18 C19 C20 -176.79(10) . . . . ?
C17 C18 C23 C22 176.58(10) . . . . ?
C24 C4 C5 C6 177.67(10) . . . . ?
C23 C18 C19 C20 0.85(16) . . . . ?
C23 C18 C17 C2 -100.74(11) . . . . ?
C23 C22 C21 C20 0.69(17) . . . . ?
C16 C15 C14 C13 177.48(11) . . . . ?
_shelx_SHELXL_version_number 2014/7
_iucr_refine_instructions_details
;
cd1394a.res created by SHELXL-2014/7
TITL cd1394a_a.res in P-1
REM Old TITL cd1394a in P-1 #2
REM SHELXT solution in P-1
REM R1 0.125, Rweak 0.005, Alpha 0.045, Orientation as input
REM Formula found by SHELXT: C25
CELL 0.71075 8.9502 9.1881 11.6731 83.963 70.783 77.642
ZERR 2 0.0006 0.0005 0.0008 0.006 0.005 0.005
LATT 1
SFAC C H N
UNIT 48 46 2
L.S. 5
PLAN 5
SIZE 0.5 0.33 0.1
TEMP 98.15
BOND $H
LIST 4
ACTA
fmap 2 53
MORE -1
CONF
OMIT -3 55
REM
REM
REM
WGHT 0.055000 0.293000
FVAR 1.63073
N1 3 0.533000 0.606073 0.599114 11.00000 0.01773 0.01824 =
0.01929 0.00203 -0.00514 -0.00549
C3 1 0.556055 0.446641 0.756198 11.00000 0.01717 0.01761 =
0.01911 -0.00158 -0.00634 -0.00620
C2 1 0.393105 0.530772 0.786892 11.00000 0.01769 0.01695 =
0.01863 -0.00082 -0.00642 -0.00464
C10 1 0.654556 0.814559 0.475962 11.00000 0.01470 0.01562 =
0.01915 0.00018 -0.00370 -0.00185
C18 1 0.099400 0.619317 0.889350 11.00000 0.01725 0.02171 =
0.01394 0.00211 -0.00224 -0.00525
C1 1 0.386720 0.624848 0.689132 11.00000 0.01754 0.01784 =
0.02017 0.00014 -0.00453 -0.00528
AFIX 43
H1 2 0.295365 0.692619 0.684236 11.00000 -1.20000
AFIX 0
C8 1 0.639350 0.497874 0.638160 11.00000 0.01939 0.01609 =
0.02074 -0.00029 -0.00744 -0.00650
C7 1 0.801002 0.439949 0.577276 11.00000 0.01902 0.02139 =
0.02236 -0.00162 -0.00445 -0.00712
AFIX 43
H7 2 0.853259 0.475448 0.499977 11.00000 -1.20000
AFIX 0
C11 1 0.680791 0.857725 0.577028 11.00000 0.02261 0.02068 =
0.02118 0.00230 -0.00909 -0.00499
AFIX 43
H11 2 0.642099 0.809656 0.651961 11.00000 -1.20000
AFIX 0
C4 1 0.638978 0.331020 0.814924 11.00000 0.02084 0.01860 =
0.02234 0.00019 -0.00976 -0.00648
C15 1 0.709230 0.889780 0.363824 11.00000 0.01968 0.01736 =
0.01887 -0.00011 -0.00236 -0.00108
C19 1 0.015141 0.576203 0.821449 11.00000 0.02246 0.02686 =
0.02042 -0.00174 -0.00660 -0.00481
AFIX 43
H19 2 0.050976 0.483622 0.786291 11.00000 -1.20000
AFIX 0
C9 1 0.567656 0.688165 0.483440 11.00000 0.02119 0.02036 =
0.01647 0.00171 -0.00501 -0.00768
AFIX 23
H9A 2 0.466928 0.728366 0.467150 11.00000 -1.20000
H9B 2 0.632730 0.619314 0.420267 11.00000 -1.20000
AFIX 0
C17 1 0.252511 0.520697 0.900629 11.00000 0.01832 0.02102 =
0.01627 0.00042 -0.00528 -0.00463
AFIX 23
H17A 2 0.237298 0.418195 0.915904 11.00000 -1.20000
H17B 2 0.276128 0.550305 0.969187 11.00000 -1.20000
AFIX 0
C5 1 0.799296 0.274807 0.753564 11.00000 0.02172 0.02017 =
0.02826 0.00058 -0.01159 -0.00322
AFIX 43
H5 2 0.855968 0.199013 0.791079 11.00000 -1.20000
AFIX 0
C14 1 0.795100 1.001847 0.355547 11.00000 0.02321 0.01782 =
0.02647 0.00465 -0.00234 -0.00385
AFIX 43
H14 2 0.834627 1.050129 0.280855 11.00000 -1.20000
AFIX 0
C24 1 0.555722 0.266575 0.938400 11.00000 0.02219 0.02537 =
0.02226 0.00570 -0.00999 -0.00570
AFIX 137
H24A 2 0.508020 0.345192 0.994880 11.00000 -1.50000
H24B 2 0.633051 0.195061 0.965950 11.00000 -1.50000
H24C 2 0.473229 0.218550 0.932776 11.00000 -1.50000
AFIX 0
C23 1 0.041770 0.757358 0.942097 11.00000 0.02471 0.02330 =
0.01899 -0.00048 -0.00366 -0.00619
AFIX 43
H23 2 0.095197 0.787620 0.988876 11.00000 -1.20000
AFIX 0
C6 1 0.879439 0.327923 0.636907 11.00000 0.01648 0.02327 =
0.02895 -0.00361 -0.00582 -0.00345
AFIX 43
H6 2 0.987142 0.286814 0.599341 11.00000 -1.20000
AFIX 0
C20 1 -0.120990 0.668793 0.805417 11.00000 0.02356 0.04044 =
0.02341 0.00264 -0.01012 -0.00664
AFIX 43
H20 2 -0.175854 0.638154 0.759909 11.00000 -1.20000
AFIX 0
C12 1 0.764236 0.971976 0.567421 11.00000 0.03131 0.02347 =
0.03209 0.00139 -0.01785 -0.00836
AFIX 43
H12 2 0.780573 1.000633 0.635779 11.00000 -1.20000
AFIX 0
C22 1 -0.094607 0.850949 0.925988 11.00000 0.02912 0.02151 =
0.02291 0.00183 0.00039 -0.00049
AFIX 43
H22 2 -0.131352 0.943217 0.961647 11.00000 -1.20000
AFIX 0
C21 1 -0.175655 0.807418 0.857267 11.00000 0.02123 0.03558 =
0.02366 0.00905 -0.00335 0.00142
AFIX 43
H21 2 -0.266221 0.870458 0.845763 11.00000 -1.20000
AFIX 0
C13 1 0.822962 1.043019 0.456115 11.00000 0.02550 0.01848 =
0.04027 0.00402 -0.01345 -0.00831
AFIX 43
H13 2 0.880924 1.118136 0.448918 11.00000 -1.20000
AFIX 0
C16 1 0.675144 0.851992 0.253844 11.00000 0.04602 0.02628 =
0.01730 0.00079 -0.00623 -0.00980
AFIX 137
H16A 2 0.736073 0.755130 0.227857 11.00000 -1.50000
H16B 2 0.705378 0.924870 0.189654 11.00000 -1.50000
H16C 2 0.562208 0.851837 0.273770 11.00000 -1.50000
AFIX 0
HKLF 4
REM cd1394a_a.res in P-1
REM R1 = 0.0410 for 3573 Fo > 4sig(Fo) and 0.0462 for all 4038 data
REM 228 parameters refined using 0 restraints
END
WGHT 0.0550 0.2913
REM Highest difference peak 0.311, deepest hole -0.200, 1-sigma level 0.040
Q1 1 0.4749 0.4778 0.7824 11.00000 0.05 0.31
Q2 1 0.7163 0.3002 0.7787 11.00000 0.05 0.30
Q3 1 0.5991 0.4634 0.6944 11.00000 0.05 0.28
Q4 1 0.6244 0.7480 0.4813 11.00000 0.05 0.28
Q5 1 0.6872 0.8468 0.4213 11.00000 0.05 0.28
REM The information below was added by Olex2.
REM
REM R1 = 0.0410 for 3573 Fo > 4sig(Fo) and 0.0462 for all 6971 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.31, deepest hole -0.20
REM Mean Shift 0, Max Shift 0.000.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0462
REM R1_gt = 0.0410
REM wR_ref = 0.1105
REM GOOF = 1.039
REM Shift_max = 0.000
REM Shift_mean = 0
REM Reflections_all = 6971
REM Reflections_gt = 3573
REM Parameters = n/a
REM Hole = -0.20
REM Peak = 0.31
REM Flack = n/a
;
_olex2_exptl_crystal_mounting_method 'glass fiber'
_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_cd1399a
_database_code_depnum_ccdc_archive 'CCDC 1457714'
_audit_update_record
;
2016-03-03 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;
_audit_creation_date 2016-01-06
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C8 H8 Cl N O'
_chemical_formula_sum 'C8 H8 Cl N O'
_chemical_formula_weight 169.60
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0061 0.0033 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
_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 11.461(3)
_cell_length_b 18.171(5)
_cell_length_c 7.917(2)
_cell_angle_alpha 90
_cell_angle_beta 106.770(4)
_cell_angle_gamma 90
_cell_volume 1578.7(7)
_cell_formula_units_Z 8
_cell_measurement_reflns_used 7742
_cell_measurement_temperature 98
_cell_measurement_theta_max 40.2
_cell_measurement_theta_min 2.2
_shelx_estimated_absorpt_T_max 0.921
_shelx_estimated_absorpt_T_min 0.921
_exptl_absorpt_coefficient_mu 0.419
_exptl_absorpt_correction_T_max 1.000
_exptl_absorpt_correction_T_min 0.916
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)'
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier .
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.427
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 704
_exptl_crystal_recrystallization_method 'vapor diffusion of hexane into toluene'
_exptl_crystal_size_max 0.2
_exptl_crystal_size_mid 0.2
_exptl_crystal_size_min 0.2
_exptl_special_details
;
?
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0453
_diffrn_reflns_av_unetI/netI 0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_k_max 23
_diffrn_reflns_limit_k_min -23
_diffrn_reflns_limit_l_max 10
_diffrn_reflns_limit_l_min -10
_diffrn_reflns_number 12469
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 27.499
_diffrn_reflns_theta_min 1.856
_diffrn_ambient_temperature 98
_diffrn_detector CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
scan:
Number of images: 246
Slice: -68.0000 - 55.0000
Image width: 0.5000
Exp time: 25.0000
Rotation axis: Omega
Omega: 0.0000
Kappa: 70.0000
Phi: 270.0000
XTD: 34.4856
2theta: -34.7367
scan:
Number of images: 164
Slice: -49.0000 - 33.0000
Image width: 0.5000
Exp time: 25.0000
Rotation axis: Omega
Omega: 0.0000
Kappa: 70.0000
Phi: 90.0000
XTD: 34.4856
2theta: -34.7367
scan:
Number of images: 136
Slice: -88.0000 - -20.0000
Image width: 0.5000
Exp time: 25.0000
Rotation axis: Omega
Omega: 0.0000
Kappa: 0.0000
Phi: 270.0000
XTD: 34.4856
2theta: -34.7367
scan:
Number of images: 92
Slice: -61.0000 - -15.0000
Image width: 0.5000
Exp time: 25.0000
Rotation axis: Omega
Omega: 0.0000
Kappa: 70.0000
Phi: 0.0000
XTD: 34.4856
2theta: -34.7367
scan:
Number of images: 62
Slice: -115.0000 - -84.0000
Image width: 0.5000
Exp time: 25.0000
Rotation axis: Omega
Omega: 0.0000
Kappa: 0.0000
Phi: 180.0000
XTD: 34.4856
2theta: -34.7367
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type d*Trek
_diffrn_orient_matrix_UB_11 -0.103867
_diffrn_orient_matrix_UB_12 0.081254
_diffrn_orient_matrix_UB_13 0.003521
_diffrn_orient_matrix_UB_21 -0.020832
_diffrn_orient_matrix_UB_22 -0.024699
_diffrn_orient_matrix_UB_23 -0.044549
_diffrn_orient_matrix_UB_31 -0.063160
_diffrn_orient_matrix_UB_32 -0.040298
_diffrn_orient_matrix_UB_33 0.051877
_diffrn_radiation_monochromator 'Graphite Monochromator'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71075
_diffrn_source 'Sealed Tube'
_diffrn_source_current 40.0
_diffrn_source_power 2.0
_diffrn_source_voltage 50.0
_diffrn_special_details
;
?
;
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 3489
_reflns_number_total 3617
_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
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2008)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.345
_refine_diff_density_min -0.281
_refine_diff_density_rms 0.051
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.057
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 201
_refine_ls_number_reflns 3617
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0341
_refine_ls_R_factor_gt 0.0328
_refine_ls_restrained_S_all 1.057
_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^)+(0.0320P)^2^+0.7660P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0803
_refine_ls_wR_factor_ref 0.0816
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
C9(H9A,H9B), C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
C12(H12), C8(H8), C4(H4), C16(H16), C14(H14), C7(H7), C13(H13), C15(H15),
C6(H6), C5(H5)
2.c Idealised tetrahedral OH refined as rotating group:
O2(H2), O1(H1)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl -0.14083(3) 0.27016(2) 0.18326(4) 0.01962(9) Uani 1 1 d . . . . .
Cl1 Cl 0.64836(3) 0.35573(2) 0.77681(4) 0.02046(9) Uani 1 1 d . . . . .
O2 O 0.15720(8) 0.26890(5) 0.35810(13) 0.0198(2) Uani 1 1 d . . . . .
H2 H 0.2180 0.2567 0.4368 0.030 Uiso 1 1 calc GR . . . .
O1 O 0.34266(9) 0.36591(5) 0.65999(13) 0.0222(2) Uani 1 1 d . . . . .
H1 H 0.2794 0.3783 0.5862 0.033 Uiso 1 1 calc GR . . . .
N2 N 0.13657(9) 0.34458(5) 0.37085(14) 0.0162(2) Uani 1 1 d . . . . .
N1 N 0.35816(9) 0.28972(6) 0.65099(14) 0.0172(2) Uani 1 1 d . . . . .
C11 C 0.01420(11) 0.44702(7) 0.24876(15) 0.0153(2) Uani 1 1 d . . . . .
C3 C 0.47853(11) 0.18596(7) 0.76733(15) 0.0151(2) Uani 1 1 d . . . . .
C2 C 0.45587(11) 0.26626(6) 0.76282(15) 0.0145(2) Uani 1 1 d . . . . .
C10 C 0.04508(11) 0.36799(6) 0.24645(16) 0.0143(2) Uani 1 1 d . . . . .
C12 C 0.10263(12) 0.49872(7) 0.33152(17) 0.0193(3) Uani 1 1 d . . . . .
H12 H 0.1826 0.4837 0.3828 0.023 Uiso 1 1 calc R . . . .
C8 C 0.59793(11) 0.15888(7) 0.82375(16) 0.0171(2) Uani 1 1 d . . . . .
H8 H 0.6630 0.1912 0.8631 0.020 Uiso 1 1 calc R . . . .
C9 C -0.02950(11) 0.31854(7) 0.10385(16) 0.0163(2) Uani 1 1 d . . . . .
H9A H 0.0233 0.2835 0.0696 0.020 Uiso 1 1 calc R . . . .
H9B H -0.0704 0.3476 0.0010 0.020 Uiso 1 1 calc R . . . .
C1 C 0.54506(11) 0.31641(7) 0.88645(15) 0.0163(2) Uani 1 1 d . . . . .
H1A H 0.5909 0.2889 0.9892 0.020 Uiso 1 1 calc R . . . .
H1B H 0.5014 0.3554 0.9259 0.020 Uiso 1 1 calc R . . . .
C4 C 0.38163(12) 0.13646(7) 0.71179(17) 0.0193(3) Uani 1 1 d . . . . .
H4 H 0.3020 0.1539 0.6738 0.023 Uiso 1 1 calc R . . . .
C16 C -0.10545(12) 0.47073(7) 0.17103(17) 0.0188(3) Uani 1 1 d . . . . .
H16 H -0.1648 0.4371 0.1133 0.023 Uiso 1 1 calc R . . . .
C14 C -0.04789(13) 0.59533(7) 0.26255(17) 0.0219(3) Uani 1 1 d . . . . .
H14 H -0.0685 0.6446 0.2680 0.026 Uiso 1 1 calc R . . . .
C7 C 0.61917(12) 0.08355(7) 0.82091(17) 0.0217(3) Uani 1 1 d . . . . .
H7 H 0.6987 0.0659 0.8554 0.026 Uiso 1 1 calc R . . . .
C13 C 0.07183(13) 0.57218(7) 0.33765(18) 0.0223(3) Uani 1 1 d . . . . .
H13 H 0.1314 0.6062 0.3922 0.027 Uiso 1 1 calc R . . . .
C15 C -0.13583(12) 0.54471(8) 0.17998(17) 0.0220(3) Uani 1 1 d . . . . .
H15 H -0.2158 0.5600 0.1300 0.026 Uiso 1 1 calc R . . . .
C6 C 0.52281(13) 0.03471(8) 0.76708(19) 0.0254(3) Uani 1 1 d . . . . .
H6 H 0.5375 -0.0156 0.7670 0.030 Uiso 1 1 calc R . . . .
C5 C 0.40381(13) 0.06121(7) 0.71311(19) 0.0239(3) Uani 1 1 d . . . . .
H5 H 0.3389 0.0285 0.6778 0.029 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
Cl2 0.01533(15) 0.01784(16) 0.02348(16) 0.00274(11) 0.00207(12) -0.00327(11)
Cl1 0.01860(16) 0.02040(16) 0.02247(16) 0.00028(11) 0.00605(12) -0.00301(11)
O2 0.0167(4) 0.0103(4) 0.0281(5) -0.0011(3) -0.0003(4) 0.0024(3)
O1 0.0197(4) 0.0123(4) 0.0284(5) -0.0012(3) -0.0028(4) 0.0029(4)
N2 0.0148(5) 0.0100(5) 0.0230(5) -0.0010(4) 0.0040(4) 0.0005(4)
N1 0.0164(5) 0.0121(5) 0.0216(5) -0.0006(4) 0.0028(4) 0.0007(4)
C11 0.0166(6) 0.0139(6) 0.0147(5) 0.0010(4) 0.0036(4) 0.0011(5)
C3 0.0171(5) 0.0159(6) 0.0125(5) 0.0015(4) 0.0044(4) 0.0022(5)
C2 0.0140(5) 0.0162(6) 0.0139(5) -0.0001(4) 0.0049(4) -0.0002(4)
C10 0.0133(5) 0.0137(5) 0.0164(5) -0.0005(4) 0.0049(4) -0.0015(4)
C12 0.0179(6) 0.0158(6) 0.0219(6) 0.0011(5) 0.0020(5) -0.0001(5)
C8 0.0163(6) 0.0200(6) 0.0135(5) 0.0011(4) 0.0022(4) 0.0014(5)
C9 0.0163(5) 0.0154(6) 0.0165(5) -0.0010(4) 0.0037(4) -0.0021(5)
C1 0.0158(5) 0.0183(6) 0.0143(5) -0.0006(4) 0.0037(4) -0.0004(5)
C4 0.0157(6) 0.0182(6) 0.0236(6) 0.0014(5) 0.0050(5) 0.0012(5)
C16 0.0173(6) 0.0181(6) 0.0186(6) 0.0002(5) 0.0014(5) 0.0007(5)
C14 0.0301(7) 0.0136(6) 0.0211(6) 0.0026(4) 0.0056(5) 0.0054(5)
C7 0.0203(6) 0.0223(6) 0.0197(6) 0.0024(5) 0.0011(5) 0.0073(5)
C13 0.0248(7) 0.0157(6) 0.0233(6) -0.0004(5) 0.0021(5) -0.0024(5)
C15 0.0203(6) 0.0211(6) 0.0223(6) 0.0030(5) 0.0024(5) 0.0078(5)
C6 0.0308(7) 0.0155(6) 0.0267(7) 0.0019(5) 0.0034(6) 0.0046(6)
C5 0.0236(7) 0.0170(6) 0.0290(7) 0.0010(5) 0.0042(5) -0.0024(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
Cl2 C9 1.8054(13) . ?
Cl1 C1 1.8052(13) . ?
O2 H2 0.8200 . ?
O2 N2 1.4040(13) . ?
O1 H1 0.8200 . ?
O1 N1 1.4001(13) . ?
N2 C10 1.2862(16) . ?
N1 C2 1.2835(16) . ?
C11 C10 1.4804(17) . ?
C11 C12 1.3985(17) . ?
C11 C16 1.3992(17) . ?
C3 C2 1.4807(17) . ?
C3 C8 1.4006(17) . ?
C3 C4 1.3978(18) . ?
C2 C1 1.5020(16) . ?
C10 C9 1.5019(16) . ?
C12 H12 0.9300 . ?
C12 C13 1.3852(18) . ?
C8 H8 0.9300 . ?
C8 C7 1.3916(18) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C4 H4 0.9300 . ?
C4 C5 1.3903(18) . ?
C16 H16 0.9300 . ?
C16 C15 1.3954(18) . ?
C14 H14 0.9300 . ?
C14 C13 1.3937(19) . ?
C14 C15 1.382(2) . ?
C7 H7 0.9300 . ?
C7 C6 1.385(2) . ?
C13 H13 0.9300 . ?
C15 H15 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.392(2) . ?
C5 H5 0.9300 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 O2 H2 109.5 . . ?
N1 O1 H1 109.5 . . ?
C10 N2 O2 112.70(10) . . ?
C2 N1 O1 113.05(10) . . ?
C12 C11 C10 120.92(11) . . ?
C12 C11 C16 119.01(11) . . ?
C16 C11 C10 120.05(11) . . ?
C8 C3 C2 120.16(11) . . ?
C4 C3 C2 120.57(11) . . ?
C4 C3 C8 119.26(11) . . ?
N1 C2 C3 117.13(11) . . ?
N1 C2 C1 122.83(11) . . ?
C3 C2 C1 120.04(10) . . ?
N2 C10 C11 117.15(11) . . ?
N2 C10 C9 122.63(11) . . ?
C11 C10 C9 120.22(10) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.41(12) . . ?
C13 C12 H12 119.8 . . ?
C3 C8 H8 120.0 . . ?
C7 C8 C3 119.99(12) . . ?
C7 C8 H8 120.0 . . ?
Cl2 C9 H9A 109.7 . . ?
Cl2 C9 H9B 109.7 . . ?
C10 C9 Cl2 109.61(9) . . ?
C10 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
Cl1 C1 H1A 109.6 . . ?
Cl1 C1 H1B 109.6 . . ?
C2 C1 Cl1 110.14(8) . . ?
C2 C1 H1A 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.24(12) . . ?
C5 C4 H4 119.9 . . ?
C11 C16 H16 119.9 . . ?
C15 C16 C11 120.10(12) . . ?
C15 C16 H16 119.9 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C15 C14 C13 119.66(12) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 C8 120.51(12) . . ?
C6 C7 H7 119.7 . . ?
C12 C13 C14 120.36(12) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C16 C15 H15 119.8 . . ?
C14 C15 C16 120.44(12) . . ?
C14 C15 H15 119.8 . . ?
C7 C6 H6 120.1 . . ?
C7 C6 C5 119.77(13) . . ?
C5 C6 H6 120.1 . . ?
C4 C5 C6 120.22(13) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
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 N2 C10 C11 179.19(10) . . . . ?
O2 N2 C10 C9 -0.41(17) . . . . ?
O1 N1 C2 C3 178.18(10) . . . . ?
O1 N1 C2 C1 -1.49(17) . . . . ?
N2 C10 C9 Cl2 82.27(13) . . . . ?
N1 C2 C1 Cl1 -83.66(13) . . . . ?
C11 C10 C9 Cl2 -97.32(12) . . . . ?
C11 C12 C13 C14 0.5(2) . . . . ?
C11 C16 C15 C14 1.2(2) . . . . ?
C3 C2 C1 Cl1 96.68(12) . . . . ?
C3 C8 C7 C6 -1.74(19) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
C2 C3 C8 C7 -177.35(11) . . . . ?
C2 C3 C4 C5 178.72(12) . . . . ?
C10 C11 C12 C13 -177.97(12) . . . . ?
C10 C11 C16 C15 177.14(12) . . . . ?
C12 C11 C10 N2 25.05(18) . . . . ?
C12 C11 C10 C9 -155.35(12) . . . . ?
C12 C11 C16 C15 -1.39(19) . . . . ?
C8 C3 C2 N1 152.94(12) . . . . ?
C8 C3 C2 C1 -27.37(17) . . . . ?
C8 C3 C4 C5 0.15(19) . . . . ?
C8 C7 C6 C5 0.9(2) . . . . ?
C4 C3 C2 N1 -25.61(17) . . . . ?
C4 C3 C2 C1 154.07(12) . . . . ?
C4 C3 C8 C7 1.22(18) . . . . ?
C16 C11 C10 N2 -153.46(12) . . . . ?
C16 C11 C10 C9 26.14(17) . . . . ?
C16 C11 C12 C13 0.56(19) . . . . ?
C7 C6 C5 C4 0.5(2) . . . . ?
C13 C14 C15 C16 -0.2(2) . . . . ?
C15 C14 C13 C12 -0.7(2) . . . . ?
_shelx_SHELXL_version_number 2014/7
_iucr_refine_instructions_details
;
cd1399a.res created by SHELXL-2014/7
TITL cd1399a_a.res in P2(1)/c
REM Old TITL cd1399a in P21/a #14
REM SHELXT solution in P2(1)/c
REM R1 0.091, Rweak 0.035, Alpha 0.016, Orientation a'=c, b'=-b, c'=a
REM Formula found by SHELXT: N2 Cl2 O2 C16
CELL 0.71075 11.461 18.1711 7.917 90 106.77 90
ZERR 8 0.0032 0.0046 0.0021 0 0.004 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC N Cl O C H
UNIT 8 8 8 64 64
L.S. 5
PLAN 10
SIZE 0.2 0.2 0.2
TEMP 98.15
BOND $H
LIST 4
ACTA
fmap 2 53
MORE -1
CONF
OMIT -3 55
REM
REM
REM
WGHT 0.032000 0.766000
FVAR 0.65685
CL2 2 -0.140829 0.270157 0.183261 11.00000 0.01533 0.01784 =
0.02348 0.00274 0.00207 -0.00327
CL1 2 0.648357 0.355731 0.776807 11.00000 0.01860 0.02040 =
0.02247 0.00028 0.00605 -0.00301
O2 3 0.157203 0.268899 0.358102 11.00000 0.01668 0.01033 =
0.02813 -0.00112 -0.00027 0.00242
AFIX 147
H2 5 0.218008 0.256730 0.436832 11.00000 -1.50000
AFIX 0
O1 3 0.342660 0.365906 0.659992 11.00000 0.01967 0.01231 =
0.02837 -0.00125 -0.00281 0.00288
AFIX 147
H1 5 0.279430 0.378254 0.586215 11.00000 -1.50000
AFIX 0
N2 1 0.136567 0.344582 0.370851 11.00000 0.01476 0.01003 =
0.02303 -0.00104 0.00403 0.00046
N1 1 0.358163 0.289722 0.650995 11.00000 0.01638 0.01206 =
0.02159 -0.00056 0.00275 0.00073
C11 4 0.014198 0.447018 0.248761 11.00000 0.01656 0.01394 =
0.01474 0.00096 0.00356 0.00110
C3 4 0.478528 0.185961 0.767325 11.00000 0.01709 0.01589 =
0.01249 0.00146 0.00441 0.00223
C2 4 0.455869 0.266259 0.762824 11.00000 0.01405 0.01616 =
0.01390 -0.00005 0.00490 -0.00023
C10 4 0.045079 0.367987 0.246452 11.00000 0.01325 0.01375 =
0.01642 -0.00046 0.00492 -0.00154
C12 4 0.102626 0.498717 0.331516 11.00000 0.01788 0.01582 =
0.02188 0.00113 0.00201 -0.00012
AFIX 43
H12 5 0.182608 0.483681 0.382750 11.00000 -1.20000
AFIX 0
C8 4 0.597934 0.158879 0.823748 11.00000 0.01633 0.02001 =
0.01350 0.00114 0.00219 0.00135
AFIX 43
H8 5 0.663013 0.191233 0.863098 11.00000 -1.20000
AFIX 0
C9 4 -0.029500 0.318544 0.103847 11.00000 0.01630 0.01544 =
0.01646 -0.00101 0.00369 -0.00208
AFIX 23
H9A 5 0.023288 0.283458 0.069567 11.00000 -1.20000
H9B 5 -0.070440 0.347591 0.001035 11.00000 -1.20000
AFIX 0
C1 4 0.545060 0.316411 0.886453 11.00000 0.01579 0.01834 =
0.01432 -0.00055 0.00369 -0.00035
AFIX 23
H1A 5 0.590868 0.288914 0.989234 11.00000 -1.20000
H1B 5 0.501399 0.355446 0.925852 11.00000 -1.20000
AFIX 0
C4 4 0.381630 0.136459 0.711793 11.00000 0.01574 0.01817 =
0.02361 0.00140 0.00502 0.00116
AFIX 43
H4 5 0.302041 0.153924 0.673828 11.00000 -1.20000
AFIX 0
C16 4 -0.105450 0.470734 0.171031 11.00000 0.01728 0.01812 =
0.01861 0.00020 0.00142 0.00069
AFIX 43
H16 5 -0.164819 0.437144 0.113314 11.00000 -1.20000
AFIX 0
C14 4 -0.047886 0.595335 0.262550 11.00000 0.03009 0.01358 =
0.02105 0.00262 0.00564 0.00544
AFIX 43
H14 5 -0.068476 0.644604 0.267979 11.00000 -1.20000
AFIX 0
C7 4 0.619169 0.083550 0.820913 11.00000 0.02028 0.02228 =
0.01968 0.00236 0.00108 0.00734
AFIX 43
H7 5 0.698697 0.065874 0.855443 11.00000 -1.20000
AFIX 0
C13 4 0.071831 0.572180 0.337652 11.00000 0.02480 0.01570 =
0.02333 -0.00041 0.00208 -0.00238
AFIX 43
H13 5 0.131365 0.606235 0.392182 11.00000 -1.20000
AFIX 0
C15 4 -0.135832 0.544705 0.179979 11.00000 0.02034 0.02105 =
0.02229 0.00301 0.00238 0.00784
AFIX 43
H15 5 -0.215806 0.560032 0.130036 11.00000 -1.20000
AFIX 0
C6 4 0.522810 0.034709 0.767081 11.00000 0.03079 0.01554 =
0.02668 0.00191 0.00335 0.00461
AFIX 43
H6 5 0.537531 -0.015620 0.766977 11.00000 -1.20000
AFIX 0
C5 4 0.403810 0.061209 0.713111 11.00000 0.02356 0.01701 =
0.02905 0.00103 0.00417 -0.00238
AFIX 43
H5 5 0.338941 0.028467 0.677826 11.00000 -1.20000
AFIX 0
HKLF 4
REM cd1399a_a.res in P2(1)/c
REM R1 = 0.0328 for 3489 Fo > 4sig(Fo) and 0.0341 for all 3617 data
REM 201 parameters refined using 0 restraints
END
WGHT 0.0317 0.7667
REM Highest difference peak 0.345, deepest hole -0.281, 1-sigma level 0.051
Q1 1 0.4347 0.1616 0.7395 11.00000 0.05 0.35
Q2 1 0.5329 0.1759 0.7800 11.00000 0.05 0.35
Q3 1 0.4650 0.2221 0.7611 11.00000 0.05 0.34
Q4 1 0.0598 0.4748 0.2854 11.00000 0.05 0.31
Q5 1 -0.0415 0.4607 0.2076 11.00000 0.05 0.30
Q6 1 0.0034 0.3421 0.1838 11.00000 0.05 0.29
Q7 1 0.6187 0.3595 0.8579 11.00000 0.05 0.28
Q8 1 0.4957 0.2867 0.8247 11.00000 0.05 0.27
Q9 1 0.0317 0.4072 0.2476 11.00000 0.05 0.26
Q10 1 0.0126 0.5798 0.2856 11.00000 0.05 0.26
REM The information below was added by Olex2.
REM
REM R1 = 0.0328 for 3489 Fo > 4sig(Fo) and 0.0341 for all 26944 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.35, deepest hole -0.28
REM Mean Shift 0, Max Shift 0.001.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0341
REM R1_gt = 0.0328
REM wR_ref = 0.0816
REM GOOF = 1.057
REM Shift_max = 0.001
REM Shift_mean = 0
REM Reflections_all = 26944
REM Reflections_gt = 3489
REM Parameters = n/a
REM Hole = -0.28
REM Peak = 0.35
REM Flack = n/a
;
_olex2_exptl_crystal_mounting_method 'cryo loop'
_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_cd1400a
_database_code_depnum_ccdc_archive 'CCDC 1457715'
_audit_update_record
;
2016-03-03 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;
_audit_creation_date 2016-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C26 H26 N2 O'
_chemical_formula_sum 'C26 H26 N2 O'
_chemical_formula_weight 382.49
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
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'
_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 6.8190(12)
_cell_length_b 8.4731(15)
_cell_length_c 17.387(3)
_cell_angle_alpha 91.130(4)
_cell_angle_beta 90.978(5)
_cell_angle_gamma 96.993(4)
_cell_volume 996.8(3)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 4412
_cell_measurement_temperature 98
_cell_measurement_theta_max 40.2
_cell_measurement_theta_min 2.4
_shelx_estimated_absorpt_T_max 0.992
_shelx_estimated_absorpt_T_min 0.964
_exptl_absorpt_coefficient_mu 0.078
_exptl_absorpt_correction_T_max 1.000
_exptl_absorpt_correction_T_min 0.876
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)'
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier .
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.274
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description plate
_exptl_crystal_F_000 408
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max 0.47
_exptl_crystal_size_mid 0.3
_exptl_crystal_size_min 0.1
_exptl_special_details
;
?
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0260
_diffrn_reflns_av_unetI/netI 0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_limit_l_min -22
_diffrn_reflns_number 7900
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 27.494
_diffrn_reflns_theta_min 2.422
_diffrn_ambient_temperature 98
_diffrn_detector CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
scan:
Number of images: 246
Slice: -68.0000 - 55.0000
Image width: 0.5000
Exp time: 30.0000
Rotation axis: Omega
Omega: 0.0000
Kappa: 70.0000
Phi: 270.0000
XTD: 34.4933
2theta: -34.7450
scan:
Number of images: 150
Slice: -68.0000 - 7.0000
Image width: 0.5000
Exp time: 30.0000
Rotation axis: Omega
Omega: 0.0000
Kappa: 70.0000
Phi: 90.0000
XTD: 34.4933
2theta: -34.7450
scan:
Number of images: 128
Slice: -9.0000 - 55.0000
Image width: 0.5000
Exp time: 30.0000
Rotation axis: Omega
Omega: 0.0000
Kappa: 70.0000
Phi: 0.0000
XTD: 34.4933
2theta: -34.7450
scan:
Number of images: 106
Slice: -85.0000 - -32.0000
Image width: 0.5000
Exp time: 30.0000
Rotation axis: Omega
Omega: 0.0000
Kappa: 0.0000
Phi: 90.0000
XTD: 34.4933
2theta: -34.7450
scan:
Number of images: 62
Slice: -25.0000 - 6.0000
Image width: 0.5000
Exp time: 30.0000
Rotation axis: Omega
Omega: 0.0000
Kappa: 0.0000
Phi: 0.0000
XTD: 34.4933
2theta: -34.7450
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type d*Trek
_diffrn_orient_matrix_UB_11 -0.019987
_diffrn_orient_matrix_UB_12 0.077058
_diffrn_orient_matrix_UB_13 -0.124501
_diffrn_orient_matrix_UB_21 -0.107972
_diffrn_orient_matrix_UB_22 -0.042450
_diffrn_orient_matrix_UB_23 -0.026181
_diffrn_orient_matrix_UB_31 -0.025248
_diffrn_orient_matrix_UB_32 0.042702
_diffrn_orient_matrix_UB_33 0.029143
_diffrn_radiation_monochromator 'Graphite Monochromator'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71075
_diffrn_source 'Sealed Tube'
_diffrn_source_current 40.0
_diffrn_source_power 2.0
_diffrn_source_voltage 50.0
_diffrn_special_details
;
?
;
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 4124
_reflns_number_total 4525
_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
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2008)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.316
_refine_diff_density_min -0.213
_refine_diff_density_rms 0.044
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.029
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 265
_refine_ls_number_reflns 4525
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0489
_refine_ls_R_factor_gt 0.0448
_refine_ls_restrained_S_all 1.029
_refine_ls_shift/su_max 0.002
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0570P)^2^+0.3900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1127
_refine_ls_wR_factor_ref 0.1168
_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:
C10(H10)
2.b Secondary CH2 refined with riding coordinates:
C18(H18A,H18B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
C5(H5), C20(H20), C6(H6), C23(H23), C16(H16), C7(H7), C22(H22), C8(H8),
C12(H12), C15(H15), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
C26(H26A,H26B,H26C), C17(H17A,H17B,H17C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.64768(13) 0.90408(10) 0.79100(5) 0.0204(2) Uani 1 1 d . . . . .
N2 N 0.48170(15) 0.64328(12) 0.76364(6) 0.0190(2) Uani 1 1 d . . . . .
N1 N 0.64608(15) 0.96685(12) 0.71442(6) 0.0199(2) Uani 1 1 d . . . . .
C4 C 0.19393(17) 0.73055(13) 0.72280(7) 0.0162(2) Uani 1 1 d . . . . .
C24 C 0.71411(17) 0.30767(14) 0.85620(7) 0.0170(2) Uani 1 1 d . . . . .
C19 C 0.58172(17) 0.41875(13) 0.84072(7) 0.0161(2) Uani 1 1 d . . . . .
C3 C 0.27772(17) 0.84847(14) 0.78551(7) 0.0172(2) Uani 1 1 d . . . . .
C9 C 0.31874(17) 0.61164(14) 0.71469(7) 0.0167(2) Uani 1 1 d . . . . .
C5 C 0.02385(17) 0.72588(14) 0.67820(7) 0.0185(2) Uani 1 1 d . . . . .
H5 H -0.0580 0.8055 0.6831 0.022 Uiso 1 1 calc R . . . .
C20 C 0.41429(17) 0.42194(14) 0.88529(7) 0.0184(2) Uani 1 1 d . . . . .
H20 H 0.3268 0.4948 0.8741 0.022 Uiso 1 1 calc R . . . .
C11 C 0.47279(19) 1.10373(14) 0.62403(7) 0.0198(2) Uani 1 1 d . . . . .
C6 C -0.02357(18) 0.59914(15) 0.62539(7) 0.0207(3) Uani 1 1 d . . . . .
H6 H -0.1379 0.5941 0.5950 0.025 Uiso 1 1 calc R . . . .
C1 C 0.48558(18) 1.02654(13) 0.69929(7) 0.0180(2) Uani 1 1 d . . . . .
C18 C 0.62871(17) 0.53691(14) 0.77701(7) 0.0195(2) Uani 1 1 d . . . . .
H18A H 0.7539 0.6002 0.7895 0.023 Uiso 1 1 calc R . . . .
H18B H 0.6452 0.4781 0.7296 0.023 Uiso 1 1 calc R . . . .
C21 C 0.37397(18) 0.31916(15) 0.94624(7) 0.0198(2) Uani 1 1 d . . . . .
C23 C 0.67194(19) 0.20373(14) 0.91640(7) 0.0204(2) Uani 1 1 d . . . . .
H23 H 0.7569 0.1287 0.9271 0.024 Uiso 1 1 calc R . . . .
C16 C 0.2957(2) 1.08955(15) 0.58183(8) 0.0246(3) Uani 1 1 d . . . . .
H16 H 0.1828 1.0336 0.6018 0.029 Uiso 1 1 calc R . . . .
C26 C 0.89666(18) 0.30058(15) 0.80929(7) 0.0216(3) Uani 1 1 d . . . . .
H26A H 0.8589 0.2701 0.7571 0.032 Uiso 1 1 calc GR . . . .
H26B H 0.9736 0.2238 0.8306 0.032 Uiso 1 1 calc GR . . . .
H26C H 0.9738 0.4033 0.8102 0.032 Uiso 1 1 calc GR . . . .
C2 C 0.32020(17) 1.01826(14) 0.75560(7) 0.0182(2) Uani 1 1 d . . . . .
H2A H 0.2024 1.0485 0.7307 0.022 Uiso 1 1 calc R . . . .
H2B H 0.3565 1.0920 0.7983 0.022 Uiso 1 1 calc R . . . .
C7 C 0.10021(19) 0.48121(15) 0.61844(7) 0.0211(3) Uani 1 1 d . . . . .
H7 H 0.0669 0.3976 0.5834 0.025 Uiso 1 1 calc R . . . .
C22 C 0.50522(19) 0.20973(15) 0.96096(7) 0.0211(3) Uani 1 1 d . . . . .
H22 H 0.4814 0.1395 1.0011 0.025 Uiso 1 1 calc R . . . .
C8 C 0.27345(18) 0.48502(14) 0.66280(7) 0.0206(3) Uani 1 1 d . . . . .
H8 H 0.3556 0.4056 0.6578 0.025 Uiso 1 1 calc R . . . .
C10 C 0.47932(17) 0.78984(14) 0.80653(7) 0.0180(2) Uani 1 1 d . . . . .
H10 H 0.4809 0.7667 0.8615 0.022 Uiso 1 1 calc R . . . .
C17 C 0.14184(19) 0.84519(16) 0.85501(7) 0.0225(3) Uani 1 1 d . . . . .
H17A H 0.0166 0.8763 0.8395 0.034 Uiso 1 1 calc GR . . . .
H17B H 0.2014 0.9177 0.8943 0.034 Uiso 1 1 calc GR . . . .
H17C H 0.1225 0.7396 0.8748 0.034 Uiso 1 1 calc GR . . . .
C12 C 0.6404(2) 1.19111(16) 0.59419(8) 0.0245(3) Uani 1 1 d . . . . .
H12 H 0.7594 1.2015 0.6218 0.029 Uiso 1 1 calc R . . . .
C15 C 0.2868(2) 1.15831(16) 0.51022(8) 0.0294(3) Uani 1 1 d . . . . .
H15 H 0.1690 1.1458 0.4817 0.035 Uiso 1 1 calc R . . . .
C25 C 0.1958(2) 0.32953(18) 0.99541(8) 0.0271(3) Uani 1 1 d . . . . .
H25A H 0.2232 0.4165 1.0318 0.041 Uiso 1 1 calc GR . . . .
H25B H 0.1660 0.2321 1.0225 0.041 Uiso 1 1 calc GR . . . .
H25C H 0.0848 0.3466 0.9633 0.041 Uiso 1 1 calc GR . . . .
C13 C 0.6294(2) 1.26240(17) 0.52334(8) 0.0305(3) Uani 1 1 d . . . . .
H13 H 0.7408 1.3218 0.5040 0.037 Uiso 1 1 calc R . . . .
C14 C 0.4534(2) 1.24559(17) 0.48121(8) 0.0304(3) Uani 1 1 d . . . . .
H14 H 0.4471 1.2928 0.4335 0.036 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
O1 0.0169(4) 0.0201(4) 0.0239(4) 0.0024(3) -0.0016(3) 0.0006(3)
N2 0.0179(5) 0.0156(5) 0.0240(5) 0.0024(4) -0.0013(4) 0.0045(4)
N1 0.0197(5) 0.0165(5) 0.0233(5) 0.0023(4) 0.0032(4) 0.0012(4)
C4 0.0166(5) 0.0149(5) 0.0171(5) 0.0031(4) 0.0043(4) 0.0010(4)
C24 0.0157(5) 0.0157(5) 0.0195(5) -0.0021(4) -0.0014(4) 0.0022(4)
C19 0.0143(5) 0.0147(5) 0.0191(5) 0.0007(4) -0.0003(4) 0.0002(4)
C3 0.0153(5) 0.0186(6) 0.0180(5) 0.0011(4) 0.0022(4) 0.0031(4)
C9 0.0153(5) 0.0165(5) 0.0185(5) 0.0058(4) 0.0039(4) 0.0011(4)
C5 0.0155(5) 0.0191(6) 0.0212(6) 0.0041(4) 0.0039(4) 0.0027(4)
C20 0.0149(5) 0.0170(6) 0.0235(6) 0.0006(4) 0.0002(4) 0.0025(4)
C11 0.0255(6) 0.0127(5) 0.0218(6) -0.0007(4) 0.0039(5) 0.0040(4)
C6 0.0173(6) 0.0234(6) 0.0206(6) 0.0040(5) 0.0008(4) -0.0015(4)
C1 0.0195(6) 0.0117(5) 0.0224(6) -0.0017(4) 0.0018(4) 0.0002(4)
C18 0.0145(5) 0.0192(6) 0.0256(6) 0.0059(5) 0.0031(4) 0.0038(4)
C21 0.0182(6) 0.0213(6) 0.0188(5) -0.0015(4) 0.0019(4) -0.0016(4)
C23 0.0224(6) 0.0172(6) 0.0219(6) 0.0004(4) -0.0030(5) 0.0050(4)
C16 0.0286(7) 0.0174(6) 0.0270(6) 0.0014(5) -0.0011(5) 0.0000(5)
C26 0.0177(6) 0.0228(6) 0.0254(6) 0.0002(5) 0.0010(5) 0.0070(5)
C2 0.0171(5) 0.0165(6) 0.0215(6) -0.0009(4) 0.0011(4) 0.0038(4)
C7 0.0229(6) 0.0187(6) 0.0208(6) -0.0006(4) 0.0035(5) -0.0017(5)
C22 0.0259(6) 0.0189(6) 0.0180(5) 0.0026(4) -0.0002(5) -0.0002(5)
C8 0.0199(6) 0.0165(6) 0.0255(6) 0.0010(5) 0.0049(5) 0.0022(4)
C10 0.0167(6) 0.0183(6) 0.0191(5) 0.0028(4) 0.0006(4) 0.0020(4)
C17 0.0211(6) 0.0265(6) 0.0204(6) 0.0005(5) 0.0046(5) 0.0047(5)
C12 0.0243(6) 0.0240(6) 0.0257(6) 0.0011(5) 0.0067(5) 0.0041(5)
C15 0.0381(8) 0.0235(7) 0.0265(7) 0.0000(5) -0.0056(6) 0.0045(5)
C25 0.0216(6) 0.0353(7) 0.0237(6) 0.0013(5) 0.0059(5) 0.0004(5)
C13 0.0340(8) 0.0292(7) 0.0293(7) 0.0056(6) 0.0143(6) 0.0056(6)
C14 0.0462(9) 0.0263(7) 0.0209(6) 0.0036(5) 0.0065(6) 0.0116(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 N1 1.4438(13) . ?
O1 C10 1.4416(14) . ?
N2 C9 1.3846(16) . ?
N2 C18 1.4462(15) . ?
N2 C10 1.4378(15) . ?
N1 C1 1.2857(16) . ?
C4 C3 1.5200(16) . ?
C4 C9 1.4024(16) . ?
C4 C5 1.3802(17) . ?
C24 C19 1.4078(16) . ?
C24 C23 1.3924(17) . ?
C24 C26 1.5064(16) . ?
C19 C20 1.3934(16) . ?
C19 C18 1.5198(16) . ?
C3 C2 1.5354(17) . ?
C3 C10 1.5577(16) . ?
C3 C17 1.5339(16) . ?
C9 C8 1.3900(17) . ?
C5 H5 0.9300 . ?
C5 C6 1.4026(17) . ?
C20 H20 0.9300 . ?
C20 C21 1.3948(17) . ?
C11 C1 1.4803(17) . ?
C11 C16 1.3933(19) . ?
C11 C12 1.3975(18) . ?
C6 H6 0.9300 . ?
C6 C7 1.3891(18) . ?
C1 C2 1.5021(16) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C21 C22 1.3892(17) . ?
C21 C25 1.5076(17) . ?
C23 H23 0.9300 . ?
C23 C22 1.3921(18) . ?
C16 H16 0.9300 . ?
C16 C15 1.3886(19) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C7 H7 0.9300 . ?
C7 C8 1.3964(18) . ?
C22 H22 0.9300 . ?
C8 H8 0.9300 . ?
C10 H10 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C12 H12 0.9300 . ?
C12 C13 1.3875(19) . ?
C15 H15 0.9300 . ?
C15 C14 1.387(2) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C13 H13 0.9300 . ?
C13 C14 1.386(2) . ?
C14 H14 0.9300 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 N1 113.89(9) . . ?
C9 N2 C18 125.21(10) . . ?
C9 N2 C10 111.92(10) . . ?
C10 N2 C18 122.61(10) . . ?
C1 N1 O1 111.95(10) . . ?
C9 C4 C3 109.10(10) . . ?
C5 C4 C3 130.37(11) . . ?
C5 C4 C9 120.52(11) . . ?
C19 C24 C26 121.31(11) . . ?
C23 C24 C19 118.13(11) . . ?
C23 C24 C26 120.56(10) . . ?
C24 C19 C18 118.92(10) . . ?
C20 C19 C24 119.76(11) . . ?
C20 C19 C18 121.28(10) . . ?
C4 C3 C2 112.14(9) . . ?
C4 C3 C10 102.91(9) . . ?
C4 C3 C17 111.58(10) . . ?
C2 C3 C10 107.89(9) . . ?
C17 C3 C2 110.44(10) . . ?
C17 C3 C10 111.62(10) . . ?
N2 C9 C4 110.25(10) . . ?
N2 C9 C8 128.54(11) . . ?
C8 C9 C4 121.21(11) . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 118.94(11) . . ?
C6 C5 H5 120.5 . . ?
C19 C20 H20 119.0 . . ?
C19 C20 C21 121.96(11) . . ?
C21 C20 H20 119.0 . . ?
C16 C11 C1 120.93(11) . . ?
C16 C11 C12 119.18(12) . . ?
C12 C11 C1 119.89(12) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 119.99(11) . . ?
C7 C6 H6 120.0 . . ?
N1 C1 C11 116.68(11) . . ?
N1 C1 C2 121.33(11) . . ?
C11 C1 C2 121.98(10) . . ?
N2 C18 C19 115.10(10) . . ?
N2 C18 H18A 108.5 . . ?
N2 C18 H18B 108.5 . . ?
C19 C18 H18A 108.5 . . ?
C19 C18 H18B 108.5 . . ?
H18A C18 H18B 107.5 . . ?
C20 C21 C25 120.79(11) . . ?
C22 C21 C20 117.85(11) . . ?
C22 C21 C25 121.34(11) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 C24 121.39(11) . . ?
C22 C23 H23 119.3 . . ?
C11 C16 H16 119.8 . . ?
C15 C16 C11 120.48(13) . . ?
C15 C16 H16 119.8 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C3 C2 H2A 109.7 . . ?
C3 C2 H2B 109.7 . . ?
C1 C2 C3 109.78(9) . . ?
C1 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C6 C7 H7 119.2 . . ?
C6 C7 C8 121.68(12) . . ?
C8 C7 H7 119.2 . . ?
C21 C22 C23 120.90(11) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C9 C8 C7 117.65(11) . . ?
C9 C8 H8 121.2 . . ?
C7 C8 H8 121.2 . . ?
O1 C10 C3 113.51(9) . . ?
O1 C10 H10 108.5 . . ?
N2 C10 O1 112.35(10) . . ?
N2 C10 C3 105.40(9) . . ?
N2 C10 H10 108.5 . . ?
C3 C10 H10 108.5 . . ?
C3 C17 H17A 109.5 . . ?
C3 C17 H17B 109.5 . . ?
C3 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.05(13) . . ?
C13 C12 H12 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 C16 119.97(14) . . ?
C14 C15 H15 120.0 . . ?
C21 C25 H25A 109.5 . . ?
C21 C25 H25B 109.5 . . ?
C21 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.37(13) . . ?
C14 C13 H13 119.8 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 119.92(13) . . ?
C13 C14 H14 120.0 . . ?
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
O1 N1 C1 C11 176.25(9) . . . . ?
O1 N1 C1 C2 -3.58(15) . . . . ?
N2 C9 C8 C7 -178.81(11) . . . . ?
N1 O1 C10 N2 69.15(12) . . . . ?
N1 O1 C10 C3 -50.31(12) . . . . ?
N1 C1 C2 C3 -47.46(15) . . . . ?
C4 C3 C2 C1 -66.93(12) . . . . ?
C4 C3 C10 O1 117.10(10) . . . . ?
C4 C3 C10 N2 -6.26(11) . . . . ?
C4 C9 C8 C7 0.63(17) . . . . ?
C4 C5 C6 C7 -0.21(17) . . . . ?
C24 C19 C20 C21 0.94(18) . . . . ?
C24 C19 C18 N2 178.23(10) . . . . ?
C24 C23 C22 C21 0.62(19) . . . . ?
C19 C24 C23 C22 -0.76(18) . . . . ?
C19 C20 C21 C22 -1.08(18) . . . . ?
C19 C20 C21 C25 177.63(11) . . . . ?
C3 C4 C9 N2 -2.63(13) . . . . ?
C3 C4 C9 C8 177.83(10) . . . . ?
C3 C4 C5 C6 -177.81(11) . . . . ?
C9 N2 C18 C19 -87.94(14) . . . . ?
C9 N2 C10 O1 -118.89(11) . . . . ?
C9 N2 C10 C3 5.20(13) . . . . ?
C9 C4 C3 C2 121.18(10) . . . . ?
C9 C4 C3 C10 5.48(12) . . . . ?
C9 C4 C3 C17 -114.33(11) . . . . ?
C9 C4 C5 C6 0.87(17) . . . . ?
C5 C4 C3 C2 -60.02(16) . . . . ?
C5 C4 C3 C10 -175.72(12) . . . . ?
C5 C4 C3 C17 64.47(16) . . . . ?
C5 C4 C9 N2 178.43(10) . . . . ?
C5 C4 C9 C8 -1.10(17) . . . . ?
C5 C6 C7 C8 -0.24(18) . . . . ?
C20 C19 C18 N2 -3.83(17) . . . . ?
C20 C21 C22 C23 0.30(18) . . . . ?
C11 C1 C2 C3 132.72(11) . . . . ?
C11 C16 C15 C14 -1.8(2) . . . . ?
C11 C12 C13 C14 -1.0(2) . . . . ?
C6 C7 C8 C9 0.03(18) . . . . ?
C1 C11 C16 C15 -178.01(12) . . . . ?
C1 C11 C12 C13 179.40(11) . . . . ?
C18 N2 C9 C4 172.43(10) . . . . ?
C18 N2 C9 C8 -8.08(19) . . . . ?
C18 N2 C10 O1 66.74(14) . . . . ?
C18 N2 C10 C3 -169.17(10) . . . . ?
C18 C19 C20 C21 -176.97(11) . . . . ?
C23 C24 C19 C20 -0.01(17) . . . . ?
C23 C24 C19 C18 177.95(11) . . . . ?
C16 C11 C1 N1 142.27(12) . . . . ?
C16 C11 C1 C2 -37.89(16) . . . . ?
C16 C11 C12 C13 -0.05(18) . . . . ?
C16 C15 C14 C13 0.8(2) . . . . ?
C26 C24 C19 C20 180.00(11) . . . . ?
C26 C24 C19 C18 -2.04(17) . . . . ?
C26 C24 C23 C22 179.24(11) . . . . ?
C2 C3 C10 O1 -1.61(13) . . . . ?
C2 C3 C10 N2 -124.96(10) . . . . ?
C10 O1 N1 C1 54.60(13) . . . . ?
C10 N2 C9 C4 -1.77(14) . . . . ?
C10 N2 C9 C8 177.72(11) . . . . ?
C10 N2 C18 C19 85.67(14) . . . . ?
C10 C3 C2 C1 45.71(12) . . . . ?
C17 C3 C2 C1 167.95(10) . . . . ?
C17 C3 C10 O1 -123.12(11) . . . . ?
C17 C3 C10 N2 113.53(11) . . . . ?
C12 C11 C1 N1 -37.17(16) . . . . ?
C12 C11 C1 C2 142.67(12) . . . . ?
C12 C11 C16 C15 1.43(19) . . . . ?
C12 C13 C14 C15 0.6(2) . . . . ?
C25 C21 C22 C23 -178.40(12) . . . . ?
_shelx_SHELXL_version_number 2014/7
_iucr_refine_instructions_details
;
cd1400a.res created by SHELXL-2014/7
TITL cd1400a_a.res in P-1
REM Old TITL cd1400a in P-1 #2
REM SHELXT solution in P-1
REM R1 0.125, Rweak 0.005, Alpha 0.035, Orientation as input
REM Formula found by SHELXT: N2 O C26
CELL 0.71075 6.819 8.4731 17.3875 91.13 90.978 96.993
ZERR 2 0.0012 0.0015 0.003 0.004 0.005 0.004
LATT 1
SFAC N O C H
UNIT 4 2 52 52
L.S. 5
PLAN 10
SIZE 0.47 0.3 0.1
TEMP 98.15
BOND $H
LIST 4
ACTA
fmap 2 53
MORE -1
CONF
OMIT -3 55
REM
REM
REM
WGHT 0.057000 0.390000
FVAR 1.39757
O1 2 0.647679 0.904076 0.790998 11.00000 0.01690 0.02013 =
0.02388 0.00243 -0.00163 0.00062
N2 1 0.481704 0.643279 0.763635 11.00000 0.01788 0.01556 =
0.02404 0.00235 -0.00133 0.00446
N1 1 0.646085 0.966849 0.714424 11.00000 0.01970 0.01647 =
0.02331 0.00227 0.00322 0.00122
C4 3 0.193929 0.730551 0.722800 11.00000 0.01659 0.01487 =
0.01706 0.00312 0.00431 0.00097
C24 3 0.714110 0.307674 0.856204 11.00000 0.01568 0.01575 =
0.01946 -0.00213 -0.00142 0.00221
C19 3 0.581719 0.418745 0.840721 11.00000 0.01427 0.01466 =
0.01910 0.00071 -0.00030 0.00020
C3 3 0.277717 0.848468 0.785512 11.00000 0.01534 0.01863 =
0.01799 0.00107 0.00224 0.00312
C9 3 0.318738 0.611638 0.714691 11.00000 0.01530 0.01646 =
0.01854 0.00577 0.00388 0.00111
C5 3 0.023851 0.725877 0.678195 11.00000 0.01554 0.01910 =
0.02123 0.00406 0.00392 0.00270
AFIX 43
H5 4 -0.058004 0.805494 0.683077 11.00000 -1.20000
AFIX 0
C20 3 0.414293 0.421938 0.885289 11.00000 0.01493 0.01697 =
0.02346 0.00061 0.00024 0.00249
AFIX 43
H20 4 0.326838 0.494762 0.874057 11.00000 -1.20000
AFIX 0
C11 3 0.472790 1.103730 0.624033 11.00000 0.02545 0.01271 =
0.02180 -0.00072 0.00394 0.00401
C6 3 -0.023566 0.599139 0.625388 11.00000 0.01730 0.02343 =
0.02056 0.00396 0.00084 -0.00149
AFIX 43
H6 4 -0.137865 0.594059 0.595027 11.00000 -1.20000
AFIX 0
C1 3 0.485583 1.026543 0.699290 11.00000 0.01947 0.01174 =
0.02237 -0.00169 0.00177 0.00024
C18 3 0.628712 0.536909 0.777014 11.00000 0.01446 0.01916 =
0.02559 0.00592 0.00312 0.00379
AFIX 23
H18A 4 0.753875 0.600221 0.789493 11.00000 -1.20000
H18B 4 0.645248 0.478086 0.729619 11.00000 -1.20000
AFIX 0
C21 3 0.373968 0.319160 0.946244 11.00000 0.01822 0.02133 =
0.01882 -0.00148 0.00194 -0.00163
C23 3 0.671939 0.203731 0.916401 11.00000 0.02242 0.01724 =
0.02195 0.00042 -0.00304 0.00496
AFIX 43
H23 4 0.756939 0.128724 0.927062 11.00000 -1.20000
AFIX 0
C16 3 0.295745 1.089545 0.581831 11.00000 0.02861 0.01740 =
0.02695 0.00143 -0.00112 -0.00004
AFIX 43
H16 4 0.182770 1.033616 0.601766 11.00000 -1.20000
AFIX 0
C26 3 0.896656 0.300576 0.809293 11.00000 0.01767 0.02279 =
0.02540 0.00019 0.00096 0.00703
AFIX 137
H26A 4 0.858878 0.270112 0.757150 11.00000 -1.50000
H26B 4 0.973631 0.223833 0.830603 11.00000 -1.50000
H26C 4 0.973789 0.403258 0.810232 11.00000 -1.50000
AFIX 0
C2 3 0.320204 1.018258 0.755597 11.00000 0.01705 0.01649 =
0.02154 -0.00095 0.00112 0.00384
AFIX 23
H2A 4 0.202411 1.048452 0.730677 11.00000 -1.20000
H2B 4 0.356482 1.091971 0.798319 11.00000 -1.20000
AFIX 0
C7 3 0.100212 0.481208 0.618441 11.00000 0.02288 0.01870 =
0.02081 -0.00062 0.00351 -0.00172
AFIX 43
H7 4 0.066860 0.397587 0.583355 11.00000 -1.20000
AFIX 0
C22 3 0.505220 0.209725 0.960961 11.00000 0.02587 0.01886 =
0.01797 0.00263 -0.00024 -0.00025
AFIX 43
H22 4 0.481381 0.139512 1.001131 11.00000 -1.20000
AFIX 0
C8 3 0.273448 0.485016 0.662800 11.00000 0.01994 0.01651 =
0.02551 0.00103 0.00493 0.00222
AFIX 43
H8 4 0.355612 0.405641 0.657801 11.00000 -1.20000
AFIX 0
C10 3 0.479321 0.789838 0.806526 11.00000 0.01671 0.01829 =
0.01913 0.00280 0.00063 0.00202
AFIX 13
H10 4 0.480914 0.766653 0.861514 11.00000 -1.20000
AFIX 0
C17 3 0.141839 0.845194 0.855014 11.00000 0.02112 0.02648 =
0.02037 0.00052 0.00460 0.00469
AFIX 137
H17A 4 0.016586 0.876254 0.839454 11.00000 -1.50000
H17B 4 0.201354 0.917703 0.894281 11.00000 -1.50000
H17C 4 0.122540 0.739575 0.874803 11.00000 -1.50000
AFIX 0
C12 3 0.640398 1.191114 0.594191 11.00000 0.02425 0.02397 =
0.02573 0.00111 0.00669 0.00407
AFIX 43
H12 4 0.759389 1.201493 0.621842 11.00000 -1.20000
AFIX 0
C15 3 0.286759 1.158309 0.510224 11.00000 0.03809 0.02352 =
0.02649 0.00001 -0.00565 0.00450
AFIX 43
H15 4 0.169010 1.145829 0.481738 11.00000 -1.20000
AFIX 0
C25 3 0.195803 0.329529 0.995407 11.00000 0.02164 0.03531 =
0.02372 0.00126 0.00587 0.00043
AFIX 137
H25A 4 0.223183 0.416458 1.031786 11.00000 -1.50000
H25B 4 0.165995 0.232116 1.022461 11.00000 -1.50000
H25C 4 0.084783 0.346617 0.963278 11.00000 -1.50000
AFIX 0
C13 3 0.629417 1.262397 0.523343 11.00000 0.03404 0.02919 =
0.02930 0.00562 0.01425 0.00564
AFIX 43
H13 4 0.740753 1.321784 0.504013 11.00000 -1.20000
AFIX 0
C14 3 0.453413 1.245587 0.481212 11.00000 0.04618 0.02627 =
0.02088 0.00355 0.00649 0.01165
AFIX 43
H14 4 0.447122 1.292795 0.433541 11.00000 -1.20000
AFIX 0
HKLF 4
REM cd1400a_a.res in P-1
REM R1 = 0.0448 for 4124 Fo > 4sig(Fo) and 0.0489 for all 4525 data
REM 265 parameters refined using 0 restraints
END
WGHT 0.0568 0.3897
REM Highest difference peak 0.316, deepest hole -0.213, 1-sigma level 0.044
Q1 1 0.3723 0.8203 0.7985 11.00000 0.05 0.32
Q2 1 0.2400 0.6637 0.7197 11.00000 0.05 0.30
Q3 1 0.2222 0.7821 0.7576 11.00000 0.05 0.29
Q4 1 0.5951 0.4655 0.8051 11.00000 0.05 0.28
Q5 1 0.4181 0.2430 0.9436 11.00000 0.05 0.28
Q6 1 0.6354 0.3451 0.8409 11.00000 0.05 0.27
Q7 1 0.4784 1.0720 0.6604 11.00000 0.05 0.27
Q8 1 0.3016 0.9265 0.7649 11.00000 0.05 0.27
Q9 1 0.3934 1.0138 0.7238 11.00000 0.05 0.26
Q10 1 0.4045 0.3772 0.9233 11.00000 0.05 0.25
REM The information below was added by Olex2.
REM
REM R1 = 0.0448 for 4124 Fo > 4sig(Fo) and 0.0489 for all 16853 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.32, deepest hole -0.21
REM Mean Shift 0, Max Shift -0.002.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0489
REM R1_gt = 0.0448
REM wR_ref = 0.1168
REM GOOF = 1.029
REM Shift_max = -0.002
REM Shift_mean = 0
REM Reflections_all = 16853
REM Reflections_gt = 4124
REM Parameters = n/a
REM Hole = -0.21
REM Peak = 0.32
REM Flack = n/a
;
_olex2_exptl_crystal_mounting_method 'nylon loop'
_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_dptoi
_database_code_depnum_ccdc_archive 'CCDC 1457716'
_audit_update_record
;
2016-03-03 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
(4aR^*^,9aR^*^)-4a,9-diallyl-3-phenyl-4,4a,9,9a-tetrahydro-[1,2]oxazino
[6,5-b]indole
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C22 H22 N2 O'
_chemical_formula_sum 'C22 H22 N2 O'
_chemical_formula_weight 330.42
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'
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M P-1
_symmetry_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 9.059(2)
_cell_length_b 9.9601(19)
_cell_length_c 11.1789(18)
_cell_angle_alpha 114.934(8)
_cell_angle_beta 101.127(13)
_cell_angle_gamma 92.311(14)
_cell_volume 889.0(3)
_cell_formula_units_Z 2
_cell_measurement_temperature 98(2)
_cell_measurement_reflns_used 4051
_cell_measurement_theta_min 2.1
_cell_measurement_theta_max 40.2
_exptl_crystal_description needle
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.54
_exptl_crystal_size_mid 0.15
_exptl_crystal_size_min 0.06
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.234
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 352
_exptl_absorpt_coefficient_mu 0.076
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.891
_exptl_absorpt_correction_T_max 1.000
_exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)'
_exptl_special_details
;
;
_diffrn_ambient_temperature 98(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type
;
Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method \w
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number 0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% <1
_diffrn_reflns_number 6937
_diffrn_reflns_av_R_equivalents 0.0375
_diffrn_reflns_av_sigmaI/netI 0.0358
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_theta_min 2.28
_diffrn_reflns_theta_max 27.50
_diffrn_reflns_reduction_process 'Lp corrections applied'
_reflns_number_total 4043
_reflns_number_gt 3675
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material 'publCIF (Westrip, 2010)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0200P)^2^+0.5200P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 4043
_refine_ls_number_parameters 292
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0476
_refine_ls_R_factor_gt 0.0438
_refine_ls_wR_factor_ref 0.0931
_refine_ls_wR_factor_gt 0.0907
_refine_ls_goodness_of_fit_ref 1.019
_refine_ls_restrained_S_all 1.019
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.66318(9) 0.53230(9) 0.00644(8) 0.01676(19) Uani 1 1 d . . .
N1 N 0.79892(11) 0.32084(12) -0.07264(10) 0.0167(2) Uani 1 1 d . . .
N2 N 0.72589(11) 0.62271(11) -0.04765(10) 0.0163(2) Uani 1 1 d . . .
C10 C 0.83746(13) 0.27615(13) -0.19711(12) 0.0149(2) Uani 1 1 d . . .
C9 C 0.97545(14) 0.23886(13) -0.23072(12) 0.0164(2) Uani 1 1 d . . .
C4 C 0.57990(13) 0.32181(13) -0.22858(12) 0.0158(2) Uani 1 1 d . . .
C1 C 0.65229(13) 0.37208(13) -0.07605(12) 0.0152(2) Uani 1 1 d . . .
C5 C 0.71085(13) 0.26780(13) -0.29535(12) 0.0156(2) Uani 1 1 d . . .
C2 C 0.65764(13) 0.58786(13) -0.17082(12) 0.0165(2) Uani 1 1 d . . .
C11 C 0.71380(13) 0.68033(14) -0.23171(12) 0.0172(2) Uani 1 1 d . . .
C3 C 0.53099(13) 0.45957(14) -0.24616(12) 0.0169(2) Uani 1 1 d . . .
C6 C 0.71915(14) 0.21905(14) -0.42902(13) 0.0190(3) Uani 1 1 d . . .
C8 C 0.98192(14) 0.19022(14) -0.36659(13) 0.0191(3) Uani 1 1 d . . .
C20 C 0.90349(14) 0.35074(14) 0.05450(12) 0.0180(2) Uani 1 1 d . . .
C16 C 0.70958(15) 0.62123(15) -0.37020(13) 0.0207(3) Uani 1 1 d . . .
C17 C 0.44298(14) 0.19792(14) -0.28059(13) 0.0190(3) Uani 1 1 d . . .
C7 C 0.85624(15) 0.17853(14) -0.46543(13) 0.0207(3) Uani 1 1 d . . .
C12 C 0.77864(15) 0.82921(14) -0.14817(13) 0.0210(3) Uani 1 1 d . . .
C18 C 0.48176(15) 0.06805(14) -0.25171(13) 0.0217(3) Uani 1 1 d . . .
C13 C 0.83718(16) 0.91562(15) -0.20214(14) 0.0237(3) Uani 1 1 d . . .
C15 C 0.76947(15) 0.70872(15) -0.42360(13) 0.0227(3) Uani 1 1 d . . .
C14 C 0.83254(15) 0.85576(15) -0.34034(14) 0.0226(3) Uani 1 1 d . . .
C21 C 0.83381(16) 0.29400(17) 0.13865(14) 0.0250(3) Uani 1 1 d . . .
C22 C 0.8479(2) 0.3709(2) 0.27023(17) 0.0389(4) Uani 1 1 d . . .
C19 C 0.41395(19) 0.02023(18) -0.18008(16) 0.0322(3) Uani 1 1 d . . .
H3B H 0.442(2) 0.491(2) -0.2060(18) 0.039 Uiso 1 1 d . . .
H17A H 0.360(2) 0.242(2) -0.2376(18) 0.039 Uiso 1 1 d . . .
H1A H 0.590(2) 0.331(2) -0.0310(18) 0.039 Uiso 1 1 d . . .
H3A H 0.502(2) 0.437(2) -0.3444(18) 0.039 Uiso 1 1 d . . .
H20A H 0.942(2) 0.462(2) 0.1094(18) 0.039 Uiso 1 1 d . . .
H7A H 0.862(2) 0.144(2) -0.5613(18) 0.039 Uiso 1 1 d . . .
H17B H 0.408(2) 0.163(2) -0.3820(18) 0.039 Uiso 1 1 d . . .
H9A H 1.062(2) 0.248(2) -0.1645(18) 0.039 Uiso 1 1 d . . .
H8A H 1.077(2) 0.161(2) -0.3926(18) 0.039 Uiso 1 1 d . . .
H18A H 0.564(2) 0.017(2) -0.2901(18) 0.039 Uiso 1 1 d . . .
H14A H 0.871(2) 0.918(2) -0.3788(18) 0.039 Uiso 1 1 d . . .
H16A H 0.667(2) 0.516(2) -0.4292(18) 0.039 Uiso 1 1 d . . .
H20B H 0.993(2) 0.300(2) 0.0295(18) 0.039 Uiso 1 1 d . . .
H21A H 0.776(2) 0.192(2) 0.0890(18) 0.039 Uiso 1 1 d . . .
H12A H 0.780(2) 0.872(2) -0.0513(19) 0.039 Uiso 1 1 d . . .
H6A H 0.630(2) 0.211(2) -0.4973(18) 0.039 Uiso 1 1 d . . .
H13A H 0.885(2) 1.021(2) -0.1400(18) 0.039 Uiso 1 1 d . . .
H15A H 0.769(2) 0.665(2) -0.5209(18) 0.039 Uiso 1 1 d . . .
H19A H 0.443(2) -0.064(2) -0.1632(18) 0.039 Uiso 1 1 d . . .
H19B H 0.329(2) 0.072(2) -0.1391(18) 0.039 Uiso 1 1 d . . .
H22B H 0.909(2) 0.474(2) 0.3212(18) 0.039 Uiso 1 1 d . . .
H22A H 0.807(2) 0.330(2) 0.3242(18) 0.039 Uiso 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 0.0197(4) 0.0156(4) 0.0163(4) 0.0074(3) 0.0067(3) 0.0007(3)
N1 0.0155(5) 0.0211(5) 0.0146(5) 0.0082(4) 0.0046(4) 0.0041(4)
N2 0.0171(5) 0.0157(5) 0.0184(5) 0.0089(4) 0.0061(4) 0.0017(4)
C10 0.0179(6) 0.0112(5) 0.0157(5) 0.0060(4) 0.0040(4) -0.0006(4)
C9 0.0164(6) 0.0142(5) 0.0181(6) 0.0071(5) 0.0035(5) 0.0005(4)
C4 0.0144(5) 0.0163(6) 0.0153(5) 0.0062(5) 0.0027(4) 0.0002(4)
C1 0.0151(5) 0.0152(6) 0.0155(5) 0.0068(5) 0.0041(4) 0.0012(4)
C5 0.0158(5) 0.0132(5) 0.0169(6) 0.0056(5) 0.0043(4) 0.0003(4)
C2 0.0155(5) 0.0159(6) 0.0188(6) 0.0076(5) 0.0051(5) 0.0036(4)
C11 0.0164(5) 0.0180(6) 0.0198(6) 0.0105(5) 0.0043(5) 0.0035(4)
C3 0.0145(5) 0.0184(6) 0.0177(6) 0.0084(5) 0.0027(5) 0.0020(4)
C6 0.0204(6) 0.0188(6) 0.0169(6) 0.0077(5) 0.0029(5) 0.0012(5)
C8 0.0194(6) 0.0169(6) 0.0226(6) 0.0084(5) 0.0089(5) 0.0022(5)
C20 0.0180(6) 0.0193(6) 0.0156(6) 0.0074(5) 0.0022(5) 0.0017(5)
C16 0.0217(6) 0.0201(6) 0.0187(6) 0.0081(5) 0.0027(5) -0.0007(5)
C17 0.0156(6) 0.0193(6) 0.0190(6) 0.0064(5) 0.0025(5) -0.0014(5)
C7 0.0256(6) 0.0199(6) 0.0171(6) 0.0073(5) 0.0082(5) 0.0029(5)
C12 0.0265(6) 0.0177(6) 0.0198(6) 0.0082(5) 0.0078(5) 0.0044(5)
C18 0.0200(6) 0.0177(6) 0.0217(6) 0.0048(5) 0.0023(5) -0.0020(5)
C13 0.0306(7) 0.0173(6) 0.0243(7) 0.0095(5) 0.0079(5) 0.0031(5)
C15 0.0252(6) 0.0250(7) 0.0195(6) 0.0110(5) 0.0056(5) 0.0022(5)
C14 0.0250(6) 0.0232(7) 0.0257(7) 0.0152(6) 0.0084(5) 0.0044(5)
C21 0.0267(7) 0.0298(7) 0.0261(7) 0.0180(6) 0.0085(6) 0.0089(6)
C22 0.0472(10) 0.0545(11) 0.0292(8) 0.0263(8) 0.0185(7) 0.0225(8)
C19 0.0403(8) 0.0276(8) 0.0325(8) 0.0154(7) 0.0121(7) 0.0015(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 N2 1.4317(13) . ?
O1 C1 1.4554(14) . ?
N1 C10 1.3906(15) . ?
N1 C1 1.4415(15) . ?
N1 C20 1.4514(15) . ?
N2 C2 1.2844(16) . ?
C10 C9 1.3939(17) . ?
C10 C5 1.3991(17) . ?
C9 C8 1.4004(17) . ?
C9 H9A 0.939(18) . ?
C4 C5 1.5194(16) . ?
C4 C3 1.5363(17) . ?
C4 C17 1.5467(17) . ?
C4 C1 1.5525(16) . ?
C1 H1A 1.001(18) . ?
C5 C6 1.3817(17) . ?
C2 C11 1.4816(17) . ?
C2 C3 1.5033(17) . ?
C11 C16 1.3970(17) . ?
C11 C12 1.4022(18) . ?
C3 H3B 0.996(18) . ?
C3 H3A 1.001(18) . ?
C6 C7 1.4028(18) . ?
C6 H6A 0.975(18) . ?
C8 C7 1.3878(18) . ?
C8 H8A 0.979(18) . ?
C20 C21 1.5004(18) . ?
C20 H20A 1.019(18) . ?
C20 H20B 0.996(18) . ?
C16 C15 1.3913(18) . ?
C16 H16A 0.981(18) . ?
C17 C18 1.4987(18) . ?
C17 H17A 0.986(18) . ?
C17 H17B 1.012(18) . ?
C7 H7A 0.990(18) . ?
C12 C13 1.3822(18) . ?
C12 H12A 0.979(18) . ?
C18 C19 1.317(2) . ?
C18 H18A 0.980(18) . ?
C13 C14 1.3930(19) . ?
C13 H13A 1.002(18) . ?
C15 C14 1.3840(19) . ?
C15 H15A 0.986(18) . ?
C14 H14A 0.978(18) . ?
C21 C22 1.318(2) . ?
C21 H21A 0.990(18) . ?
C22 H22B 1.013(19) . ?
C22 H22A 0.977(19) . ?
C19 H19A 0.973(19) . ?
C19 H19B 1.015(18) . ?
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
N2 O1 C1 114.45(8) . . ?
C10 N1 C1 111.38(10) . . ?
C10 N1 C20 125.31(10) . . ?
C1 N1 C20 121.51(10) . . ?
C2 N2 O1 112.79(10) . . ?
N1 C10 C9 129.19(11) . . ?
N1 C10 C5 109.72(10) . . ?
C9 C10 C5 121.07(11) . . ?
C10 C9 C8 117.63(11) . . ?
C10 C9 H9A 121.4(11) . . ?
C8 C9 H9A 121.0(11) . . ?
C5 C4 C3 110.67(10) . . ?
C5 C4 C17 112.71(10) . . ?
C3 C4 C17 110.84(10) . . ?
C5 C4 C1 102.87(9) . . ?
C3 C4 C1 108.08(10) . . ?
C17 C4 C1 111.33(10) . . ?
N1 C1 O1 112.30(9) . . ?
N1 C1 C4 105.13(9) . . ?
O1 C1 C4 113.50(9) . . ?
N1 C1 H1A 111.0(10) . . ?
O1 C1 H1A 101.8(10) . . ?
C4 C1 H1A 113.4(10) . . ?
C6 C5 C10 120.50(11) . . ?
C6 C5 C4 130.09(11) . . ?
C10 C5 C4 109.40(10) . . ?
N2 C2 C11 115.59(11) . . ?
N2 C2 C3 120.99(11) . . ?
C11 C2 C3 123.41(11) . . ?
C16 C11 C12 118.78(12) . . ?
C16 C11 C2 121.61(11) . . ?
C12 C11 C2 119.56(11) . . ?
C2 C3 C4 109.56(10) . . ?
C2 C3 H3B 107.2(10) . . ?
C4 C3 H3B 110.0(10) . . ?
C2 C3 H3A 110.7(10) . . ?
C4 C3 H3A 110.9(10) . . ?
H3B C3 H3A 108.5(14) . . ?
C5 C6 C7 119.33(12) . . ?
C5 C6 H6A 120.1(10) . . ?
C7 C6 H6A 120.6(10) . . ?
C7 C8 C9 121.81(12) . . ?
C7 C8 H8A 119.4(10) . . ?
C9 C8 H8A 118.8(10) . . ?
N1 C20 C21 112.16(11) . . ?
N1 C20 H20A 111.5(10) . . ?
C21 C20 H20A 109.7(10) . . ?
N1 C20 H20B 105.9(10) . . ?
C21 C20 H20B 110.6(10) . . ?
H20A C20 H20B 106.8(14) . . ?
C15 C16 C11 120.38(12) . . ?
C15 C16 H16A 120.0(10) . . ?
C11 C16 H16A 119.6(10) . . ?
C18 C17 C4 112.66(10) . . ?
C18 C17 H17A 110.0(10) . . ?
C4 C17 H17A 108.3(10) . . ?
C18 C17 H17B 109.5(10) . . ?
C4 C17 H17B 107.4(10) . . ?
H17A C17 H17B 108.9(14) . . ?
C8 C7 C6 119.63(12) . . ?
C8 C7 H7A 121.3(10) . . ?
C6 C7 H7A 119.1(10) . . ?
C13 C12 C11 120.48(12) . . ?
C13 C12 H12A 120.4(11) . . ?
C11 C12 H12A 119.1(11) . . ?
C19 C18 C17 124.55(13) . . ?
C19 C18 H18A 119.6(11) . . ?
C17 C18 H18A 115.8(10) . . ?
C12 C13 C14 120.35(13) . . ?
C12 C13 H13A 118.9(10) . . ?
C14 C13 H13A 120.7(10) . . ?
C14 C15 C16 120.36(12) . . ?
C14 C15 H15A 119.9(10) . . ?
C16 C15 H15A 119.8(10) . . ?
C15 C14 C13 119.64(12) . . ?
C15 C14 H14A 120.1(10) . . ?
C13 C14 H14A 120.2(10) . . ?
C22 C21 C20 123.63(15) . . ?
C22 C21 H21A 120.8(10) . . ?
C20 C21 H21A 115.6(10) . . ?
C21 C22 H22B 120.7(10) . . ?
C21 C22 H22A 122.4(11) . . ?
H22B C22 H22A 116.8(15) . . ?
C18 C19 H19A 121.8(11) . . ?
C18 C19 H19B 120.9(10) . . ?
H19A C19 H19B 117.4(15) . . ?
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full 27.50
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max 0.310
_refine_diff_density_min -0.225
_refine_diff_density_rms 0.043
#######################################################################
#
# 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_cd0965a
_database_code_depnum_ccdc_archive 'CCDC 1481256'
_audit_update_record
;
2016-05-22 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;
_audit_creation_date 2016-04-01
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common ?
_chemical_name_systematic
(4aR,9aR)-6-bromo-4a-ethyl-9-(2-methylbenzyl)-3-phenyl-4,4a,9,9a-tetrahydro-[1,2]oxazino[6,5-b]indole
_chemical_formula_moiety 'C26 H25 Br N2 O'
_chemical_formula_sum 'C26 H25 Br N2 O'
_chemical_formula_weight 461.39
_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'
Br Br -0.2901 2.4595 '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'
H H 0.0000 0.0000 '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 9.1842(15)
_cell_length_b 10.542(2)
_cell_length_c 11.953(2)
_cell_angle_alpha 84.992(11)
_cell_angle_beta 72.078(11)
_cell_angle_gamma 74.256(11)
_cell_volume 1059.8(3)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 4684
_cell_measurement_temperature 98
_cell_measurement_theta_max 40.2
_cell_measurement_theta_min 2.8
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 1.960
_exptl_absorpt_correction_T_max 1.000
_exptl_absorpt_correction_T_min 0.364
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)'
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier .
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.446
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description plank
_exptl_crystal_F_000 476
_exptl_crystal_size_max 0.4
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_min 0.05
_exptl_special_details
;
?
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0392
_diffrn_reflns_av_unetI/netI 0.0511
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_number 7087
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 27.499
_diffrn_reflns_theta_min 2.412
_diffrn_ambient_temperature 98
_diffrn_detector CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
scan:
Number of images: 240
Slice: -125.0000 - -5.0000
Image width: 0.5000
Exp time: 30.0000
Rotation axis: Omega
Omega: 0.0000
Kappa: 0.0000
Phi: 270.0000
XTD: 34.8119
2theta: -35.1803
scan:
Number of images: 150
Slice: -106.0000 - -31.0000
Image width: 0.5000
Exp time: 30.0000
Rotation axis: Omega
Omega: 0.0000
Kappa: 0.0000
Phi: 0.0000
XTD: 34.8119
2theta: -35.1803
scan:
Number of images: 106
Slice: -65.0000 - -12.0000
Image width: 0.5000
Exp time: 30.0000
Rotation axis: Omega
Omega: 0.0000
Kappa: 70.0000
Phi: 180.0000
XTD: 34.8119
2theta: -35.1803
scan:
Number of images: 100
Slice: -65.0000 - -15.0000
Image width: 0.5000
Exp time: 30.0000
Rotation axis: Omega
Omega: 0.0000
Kappa: 70.0000
Phi: 0.0000
XTD: 34.8119
2theta: -35.1803
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type d*Trek
_diffrn_orient_matrix_UB_11 0.107699
_diffrn_orient_matrix_UB_12 -0.045291
_diffrn_orient_matrix_UB_13 0.019456
_diffrn_orient_matrix_UB_21 0.009597
_diffrn_orient_matrix_UB_22 0.054172
_diffrn_orient_matrix_UB_23 -0.081777
_diffrn_orient_matrix_UB_31 -0.006549
_diffrn_orient_matrix_UB_32 0.073252
_diffrn_orient_matrix_UB_33 0.048195
_diffrn_radiation_monochromator 'Graphite Monochromator'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'Sealed Tube'
_diffrn_source_current 40.0
_diffrn_source_power 2.0
_diffrn_source_voltage 50.0
_diffrn_special_details
;
?
;
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 4223
_reflns_number_total 4807
_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
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2008)'
_computing_structure_solution ?
_refine_diff_density_max 0.725
_refine_diff_density_min -0.770
_refine_diff_density_rms 0.076
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.021
_refine_ls_hydrogen_treatment refxyz
_refine_ls_matrix_type full
_refine_ls_number_parameters 346
_refine_ls_number_reflns 4807
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0416
_refine_ls_R_factor_gt 0.0377
_refine_ls_restrained_S_all 1.021
_refine_ls_shift/su_max 0.002
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.4500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0867
_refine_ls_wR_factor_ref 0.0885
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H,H,H,H,H,H,H,H,H,H,H,H,H,H,H,H,H) groups
At 1.5 times of:
All C(H,H,H,H,H,H) groups
;
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.69412(3) 1.35008(2) 0.51573(2) 0.02701(9) Uani 1 1 d . . . . .
O1 O -0.01590(17) 1.09542(15) 0.71568(13) 0.0178(3) Uani 1 1 d . . . . .
N1 N 0.2264(2) 1.03875(18) 0.76807(17) 0.0186(4) Uani 1 1 d . . . . .
N2 N 0.0541(2) 1.10375(18) 0.58982(16) 0.0175(4) Uani 1 1 d . . . . .
C1 C 0.3489(2) 1.0945(2) 0.70676(19) 0.0161(4) Uani 1 1 d . . . . .
C2 C 0.5100(3) 1.0339(2) 0.6650(2) 0.0199(5) Uani 1 1 d . . . . .
C3 C 0.6122(3) 1.1117(2) 0.6070(2) 0.0197(5) Uani 1 1 d . . . . .
C4 C 0.5517(3) 1.2458(2) 0.5939(2) 0.0178(4) Uani 1 1 d . . . . .
C5 C 0.3903(2) 1.3078(2) 0.63657(19) 0.0156(4) Uani 1 1 d . . . . .
C6 C 0.2895(2) 1.2306(2) 0.69244(18) 0.0140(4) Uani 1 1 d . . . . .
C7 C 0.1100(2) 1.2677(2) 0.74449(19) 0.0152(4) Uani 1 1 d . . . . .
C8 C 0.0277(2) 1.3247(2) 0.6499(2) 0.0159(4) Uani 1 1 d . . . . .
C9 C 0.0687(2) 1.2208(2) 0.55904(19) 0.0154(4) Uani 1 1 d . . . . .
C10 C 0.0736(2) 1.1318(2) 0.7825(2) 0.0162(4) Uani 1 1 d . . . . .
H10 H 0.007(3) 1.135(2) 0.860(2) 0.019 Uiso 1 1 d R . . . .
C11 C 0.2451(3) 0.8981(2) 0.7845(2) 0.0200(5) Uani 1 1 d . . . . .
C12 C 0.2939(2) 0.8426(2) 0.8935(2) 0.0170(4) Uani 1 1 d . . . . .
C13 C 0.3115(2) 0.7077(2) 0.9196(2) 0.0197(5) Uani 1 1 d . . . . .
C14 C 0.3541(3) 0.6580(2) 1.0208(2) 0.0238(5) Uani 1 1 d . . . . .
C15 C 0.3816(3) 0.7376(3) 1.0943(2) 0.0272(5) Uani 1 1 d . . . . .
C16 C 0.3662(3) 0.8702(3) 1.0671(2) 0.0248(5) Uani 1 1 d . . . . .
C17 C 0.3228(3) 0.9223(2) 0.9674(2) 0.0204(5) Uani 1 1 d . . . . .
C18 C 0.2853(3) 0.6179(2) 0.8400(3) 0.0266(5) Uani 1 1 d . . . . .
C19 C 0.0531(3) 1.3650(2) 0.8465(2) 0.0177(4) Uani 1 1 d . . . . .
C20 C 0.1244(3) 1.3155(2) 0.9474(2) 0.0225(5) Uani 1 1 d . . . . .
C21 C 0.1333(2) 1.2445(2) 0.43104(19) 0.0151(4) Uani 1 1 d . . . . .
C23 C 0.2259(3) 1.3340(2) 0.3905(2) 0.0183(4) Uani 1 1 d . . . . .
C24 C 0.2929(3) 1.3503(2) 0.2708(2) 0.0211(5) Uani 1 1 d . . . . .
C25 C 0.2669(3) 1.2784(2) 0.1900(2) 0.0223(5) Uani 1 1 d . . . . .
C26 C 0.1724(3) 1.1906(2) 0.2300(2) 0.0210(5) Uani 1 1 d . . . . .
C27 C 0.1047(2) 1.1740(2) 0.3495(2) 0.0175(4) Uani 1 1 d . . . . .
H8A H 0.057(3) 1.409(2) 0.611(2) 0.021 Uiso 1 1 d R . . . .
H27 H 0.047(3) 1.116(3) 0.374(2) 0.021 Uiso 1 1 d R . . . .
H3 H 0.722(3) 1.075(2) 0.578(2) 0.021 Uiso 1 1 d R . . . .
H2 H 0.550(3) 0.945(3) 0.673(2) 0.021 Uiso 1 1 d R . . . .
H5 H 0.351(3) 1.400(3) 0.626(2) 0.021 Uiso 1 1 d R . . . .
H23 H 0.241(3) 1.383(2) 0.447(2) 0.021 Uiso 1 1 d R . . . .
H11A H 0.147(3) 0.880(2) 0.789(2) 0.021 Uiso 1 1 d R . . . .
H19A H -0.062(3) 1.388(2) 0.875(2) 0.021 Uiso 1 1 d R . . . .
H18A H 0.367(3) 0.611(3) 0.757(2) 0.026 Uiso 1 1 d R . . . .
H26 H 0.148(3) 1.139(2) 0.176(2) 0.021 Uiso 1 1 d R . . . .
H20A H 0.082(3) 1.234(3) 0.990(2) 0.026 Uiso 1 1 d R . . . .
H11B H 0.320(3) 0.851(2) 0.714(2) 0.021 Uiso 1 1 d R . . . .
H19B H 0.082(3) 1.446(3) 0.813(2) 0.021 Uiso 1 1 d R . . . .
H20B H 0.092(3) 1.383(3) 1.006(2) 0.026 Uiso 1 1 d R . . . .
H15 H 0.408(3) 0.696(2) 1.169(2) 0.021 Uiso 1 1 d R . . . .
H25 H 0.318(3) 1.288(3) 0.108(2) 0.021 Uiso 1 1 d R . . . .
H24 H 0.360(3) 1.409(2) 0.243(2) 0.021 Uiso 1 1 d R . . . .
H20C H 0.244(3) 1.294(3) 0.918(2) 0.026 Uiso 1 1 d R . . . .
H16 H 0.396(3) 0.926(2) 1.115(2) 0.021 Uiso 1 1 d R . . . .
H17 H 0.311(3) 1.013(3) 0.948(2) 0.021 Uiso 1 1 d R . . . .
H14 H 0.370(3) 0.573(3) 1.035(2) 0.021 Uiso 1 1 d R . . . .
H8B H -0.085(3) 1.348(2) 0.685(2) 0.021 Uiso 1 1 d R . . . .
H18B H 0.302(3) 0.531(3) 0.871(2) 0.026 Uiso 1 1 d R . . . .
H18C H 0.181(3) 0.647(3) 0.836(2) 0.026 Uiso 1 1 d 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
Br1 0.01825(13) 0.02731(14) 0.03910(17) 0.01455(10) -0.01305(10) -0.01113(9)
O1 0.0201(8) 0.0243(8) 0.0150(8) 0.0029(6) -0.0087(6) -0.0121(6)
N1 0.0197(9) 0.0156(9) 0.0248(11) 0.0063(8) -0.0120(8) -0.0074(7)
N2 0.0176(9) 0.0236(9) 0.0154(9) 0.0030(8) -0.0081(7) -0.0090(7)
C1 0.0204(10) 0.0176(10) 0.0152(11) 0.0041(8) -0.0102(8) -0.0086(8)
C2 0.0223(11) 0.0145(10) 0.0251(13) 0.0041(9) -0.0124(9) -0.0035(8)
C3 0.0140(10) 0.0226(11) 0.0235(12) 0.0025(9) -0.0096(9) -0.0025(8)
C4 0.0197(10) 0.0199(10) 0.0188(11) 0.0045(9) -0.0103(8) -0.0092(8)
C5 0.0177(10) 0.0155(10) 0.0174(11) 0.0018(8) -0.0100(8) -0.0054(8)
C6 0.0163(10) 0.0159(10) 0.0127(10) 0.0016(8) -0.0092(8) -0.0037(8)
C7 0.0160(10) 0.0163(10) 0.0155(11) 0.0010(8) -0.0069(8) -0.0056(8)
C8 0.0153(10) 0.0163(10) 0.0175(11) 0.0010(8) -0.0082(8) -0.0027(8)
C9 0.0138(9) 0.0180(10) 0.0176(11) -0.0006(8) -0.0102(8) -0.0031(8)
C10 0.0175(10) 0.0204(10) 0.0158(11) 0.0017(9) -0.0085(8) -0.0095(8)
C11 0.0241(11) 0.0172(10) 0.0261(13) 0.0052(9) -0.0144(10) -0.0109(9)
C12 0.0160(10) 0.0184(10) 0.0188(11) 0.0051(9) -0.0065(8) -0.0078(8)
C13 0.0160(10) 0.0189(11) 0.0245(12) 0.0042(9) -0.0064(9) -0.0057(8)
C14 0.0198(11) 0.0203(11) 0.0285(14) 0.0110(10) -0.0066(9) -0.0045(9)
C15 0.0199(11) 0.0373(14) 0.0203(13) 0.0083(11) -0.0056(9) -0.0036(10)
C16 0.0229(11) 0.0320(13) 0.0201(12) -0.0022(10) -0.0085(9) -0.0049(10)
C17 0.0223(11) 0.0190(11) 0.0216(12) 0.0018(9) -0.0085(9) -0.0063(9)
C18 0.0270(13) 0.0179(11) 0.0380(16) 0.0029(11) -0.0124(11) -0.0087(9)
C19 0.0198(11) 0.0189(11) 0.0170(11) -0.0007(9) -0.0080(9) -0.0062(8)
C20 0.0295(13) 0.0256(12) 0.0169(12) -0.0017(10) -0.0124(9) -0.0075(10)
C21 0.0144(10) 0.0157(10) 0.0173(11) 0.0006(8) -0.0090(8) -0.0024(8)
C23 0.0207(11) 0.0185(10) 0.0193(12) 0.0003(9) -0.0117(9) -0.0046(8)
C24 0.0193(11) 0.0242(12) 0.0216(12) 0.0044(9) -0.0073(9) -0.0083(9)
C25 0.0217(11) 0.0298(12) 0.0153(12) 0.0037(10) -0.0079(9) -0.0050(9)
C26 0.0225(11) 0.0249(11) 0.0190(12) -0.0018(9) -0.0123(9) -0.0041(9)
C27 0.0175(10) 0.0186(10) 0.0197(12) 0.0012(9) -0.0097(8) -0.0054(8)
_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
Br1 C4 1.908(2) . ?
O1 N2 1.448(2) . ?
O1 C10 1.445(2) . ?
N1 C1 1.387(3) . ?
N1 C10 1.447(3) . ?
N1 C11 1.448(3) . ?
N2 C9 1.287(3) . ?
C1 C2 1.391(3) . ?
C1 C6 1.405(3) . ?
C2 C3 1.398(3) . ?
C2 H2 0.92(3) . ?
C3 C4 1.386(3) . ?
C3 H3 0.94(3) . ?
C4 C5 1.397(3) . ?
C5 C6 1.378(3) . ?
C5 H5 0.95(3) . ?
C6 C7 1.523(3) . ?
C7 C8 1.540(3) . ?
C7 C10 1.557(3) . ?
C7 C19 1.532(3) . ?
C8 C9 1.501(3) . ?
C8 H8A 1.03(3) . ?
C8 H8B 0.96(3) . ?
C9 C21 1.487(3) . ?
C10 H10 0.94(3) . ?
C11 C12 1.525(3) . ?
C11 H11A 0.96(3) . ?
C11 H11B 0.98(3) . ?
C12 C13 1.405(3) . ?
C12 C17 1.398(3) . ?
C13 C14 1.399(3) . ?
C13 C18 1.510(3) . ?
C14 C15 1.386(4) . ?
C14 H14 0.88(3) . ?
C15 C16 1.386(4) . ?
C15 H15 1.02(3) . ?
C16 C17 1.392(3) . ?
C16 H16 0.99(2) . ?
C17 H17 0.95(3) . ?
C18 H18A 1.04(3) . ?
C18 H18B 0.95(3) . ?
C18 H18C 0.94(3) . ?
C19 C20 1.531(3) . ?
C19 H19A 0.97(3) . ?
C19 H19B 0.98(3) . ?
C20 H20A 1.06(3) . ?
C20 H20B 0.96(3) . ?
C20 H20C 1.01(3) . ?
C21 C23 1.397(3) . ?
C21 C27 1.401(3) . ?
C23 C24 1.388(3) . ?
C23 H23 0.95(2) . ?
C24 C25 1.391(3) . ?
C24 H24 0.96(3) . ?
C25 C26 1.393(3) . ?
C25 H25 0.96(3) . ?
C26 C27 1.388(3) . ?
C26 H26 0.99(2) . ?
C27 H27 0.89(3) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 N2 113.09(15) . . ?
C1 N1 C10 111.36(17) . . ?
C1 N1 C11 123.63(19) . . ?
C10 N1 C11 122.70(17) . . ?
C9 N2 O1 110.97(17) . . ?
N1 C1 C2 128.6(2) . . ?
N1 C1 C6 110.07(18) . . ?
C2 C1 C6 121.3(2) . . ?
C1 C2 C3 118.2(2) . . ?
C1 C2 H2 122.2(16) . . ?
C3 C2 H2 119.6(16) . . ?
C2 C3 H3 121.0(16) . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 119.3(16) . . ?
C3 C4 Br1 118.83(16) . . ?
C3 C4 C5 122.5(2) . . ?
C5 C4 Br1 118.71(16) . . ?
C4 C5 H5 121.0(15) . . ?
C6 C5 C4 117.73(19) . . ?
C6 C5 H5 121.3(15) . . ?
C1 C6 C7 109.36(18) . . ?
C5 C6 C1 120.57(19) . . ?
C5 C6 C7 130.06(19) . . ?
C6 C7 C8 111.29(18) . . ?
C6 C7 C10 102.71(16) . . ?
C6 C7 C19 112.33(16) . . ?
C8 C7 C10 107.14(16) . . ?
C19 C7 C8 109.88(17) . . ?
C19 C7 C10 113.21(18) . . ?
C7 C8 H8A 113.3(14) . . ?
C7 C8 H8B 109.7(15) . . ?
C9 C8 C7 108.75(17) . . ?
C9 C8 H8A 110.4(14) . . ?
C9 C8 H8B 107.9(15) . . ?
H8A C8 H8B 106.6(19) . . ?
N2 C9 C8 120.7(2) . . ?
N2 C9 C21 116.58(19) . . ?
C21 C9 C8 122.71(19) . . ?
O1 C10 N1 112.29(17) . . ?
O1 C10 C7 112.67(17) . . ?
O1 C10 H10 103.2(15) . . ?
N1 C10 C7 105.36(16) . . ?
N1 C10 H10 112.6(15) . . ?
C7 C10 H10 110.9(15) . . ?
N1 C11 C12 114.36(18) . . ?
N1 C11 H11A 108.4(15) . . ?
N1 C11 H11B 109.9(15) . . ?
C12 C11 H11A 109.2(16) . . ?
C12 C11 H11B 110.3(15) . . ?
H11A C11 H11B 104(2) . . ?
C13 C12 C11 119.17(19) . . ?
C17 C12 C11 121.6(2) . . ?
C17 C12 C13 119.2(2) . . ?
C12 C13 C18 120.7(2) . . ?
C14 C13 C12 118.8(2) . . ?
C14 C13 C18 120.5(2) . . ?
C13 C14 H14 118.6(17) . . ?
C15 C14 C13 121.8(2) . . ?
C15 C14 H14 119.4(17) . . ?
C14 C15 C16 119.1(2) . . ?
C14 C15 H15 117.8(14) . . ?
C16 C15 H15 123.0(14) . . ?
C15 C16 C17 120.2(2) . . ?
C15 C16 H16 119.6(15) . . ?
C17 C16 H16 120.0(15) . . ?
C12 C17 H17 117.8(15) . . ?
C16 C17 C12 120.9(2) . . ?
C16 C17 H17 121.3(15) . . ?
C13 C18 H18A 112.0(14) . . ?
C13 C18 H18B 109.3(16) . . ?
C13 C18 H18C 109.6(16) . . ?
H18A C18 H18B 105(2) . . ?
H18A C18 H18C 111(2) . . ?
H18B C18 H18C 109(2) . . ?
C7 C19 H19A 109.6(15) . . ?
C7 C19 H19B 106.4(15) . . ?
C20 C19 C7 113.96(19) . . ?
C20 C19 H19A 110.8(15) . . ?
C20 C19 H19B 109.8(15) . . ?
H19A C19 H19B 106(2) . . ?
C19 C20 H20A 109.7(14) . . ?
C19 C20 H20B 110.7(16) . . ?
C19 C20 H20C 110.5(15) . . ?
H20A C20 H20B 106(2) . . ?
H20A C20 H20C 113(2) . . ?
H20B C20 H20C 106(2) . . ?
C23 C21 C9 120.87(18) . . ?
C23 C21 C27 119.3(2) . . ?
C27 C21 C9 119.84(19) . . ?
C21 C23 H23 118.0(16) . . ?
C24 C23 C21 120.5(2) . . ?
C24 C23 H23 121.5(16) . . ?
C23 C24 C25 120.2(2) . . ?
C23 C24 H24 120.4(15) . . ?
C25 C24 H24 119.4(15) . . ?
C24 C25 C26 119.5(2) . . ?
C24 C25 H25 118.9(15) . . ?
C26 C25 H25 121.5(15) . . ?
C25 C26 H26 122.6(15) . . ?
C27 C26 C25 120.7(2) . . ?
C27 C26 H26 116.7(15) . . ?
C21 C27 H27 120.0(17) . . ?
C26 C27 C21 119.9(2) . . ?
C26 C27 H27 120.0(17) . . ?
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
Br1 C4 C5 C6 179.85(15) . . . . ?
O1 N2 C9 C8 4.6(2) . . . . ?
O1 N2 C9 C21 -177.61(15) . . . . ?
N1 C1 C2 C3 -178.8(2) . . . . ?
N1 C1 C6 C5 178.31(18) . . . . ?
N1 C1 C6 C7 -2.6(2) . . . . ?
N1 C11 C12 C13 178.39(19) . . . . ?
N1 C11 C12 C17 -2.2(3) . . . . ?
N2 O1 C10 N1 -67.1(2) . . . . ?
N2 O1 C10 C7 51.7(2) . . . . ?
N2 C9 C21 C23 -147.59(19) . . . . ?
N2 C9 C21 C27 30.8(3) . . . . ?
C1 N1 C10 O1 111.85(19) . . . . ?
C1 N1 C10 C7 -11.1(2) . . . . ?
C1 N1 C11 C12 88.7(3) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C1 C6 C7 C8 -118.34(19) . . . . ?
C1 C6 C7 C10 -4.0(2) . . . . ?
C1 C6 C7 C19 118.0(2) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
C2 C1 C6 C7 178.88(19) . . . . ?
C2 C3 C4 Br1 179.37(16) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
C4 C5 C6 C7 -178.0(2) . . . . ?
C5 C6 C7 C8 60.6(3) . . . . ?
C5 C6 C7 C10 175.0(2) . . . . ?
C5 C6 C7 C19 -63.1(3) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
C6 C7 C8 C9 62.4(2) . . . . ?
C6 C7 C10 O1 -113.96(18) . . . . ?
C6 C7 C10 N1 8.8(2) . . . . ?
C6 C7 C19 C20 -57.3(3) . . . . ?
C7 C8 C9 N2 49.6(3) . . . . ?
C7 C8 C9 C21 -128.1(2) . . . . ?
C8 C7 C10 O1 3.4(2) . . . . ?
C8 C7 C10 N1 126.12(18) . . . . ?
C8 C7 C19 C20 178.19(18) . . . . ?
C8 C9 C21 C23 30.1(3) . . . . ?
C8 C9 C21 C27 -151.54(19) . . . . ?
C9 C21 C23 C24 176.4(2) . . . . ?
C9 C21 C27 C26 -176.32(19) . . . . ?
C10 O1 N2 C9 -57.7(2) . . . . ?
C10 N1 C1 C2 -172.7(2) . . . . ?
C10 N1 C1 C6 8.9(2) . . . . ?
C10 N1 C11 C12 -110.0(2) . . . . ?
C10 C7 C8 C9 -49.2(2) . . . . ?
C10 C7 C19 C20 58.4(2) . . . . ?
C11 N1 C1 C2 -9.6(3) . . . . ?
C11 N1 C1 C6 172.02(19) . . . . ?
C11 N1 C10 O1 -51.4(3) . . . . ?
C11 N1 C10 C7 -174.41(19) . . . . ?
C11 C12 C13 C14 -179.1(2) . . . . ?
C11 C12 C13 C18 1.0(3) . . . . ?
C11 C12 C17 C16 179.5(2) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
C13 C12 C17 C16 -1.0(3) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C15 C16 C17 C12 0.1(4) . . . . ?
C17 C12 C13 C14 1.5(3) . . . . ?
C17 C12 C13 C18 -178.4(2) . . . . ?
C18 C13 C14 C15 178.8(2) . . . . ?
C19 C7 C8 C9 -172.57(17) . . . . ?
C19 C7 C10 O1 124.67(19) . . . . ?
C19 C7 C10 N1 -112.58(19) . . . . ?
C21 C23 C24 C25 0.7(3) . . . . ?
C23 C21 C27 C26 2.1(3) . . . . ?
C23 C24 C25 C26 0.3(3) . . . . ?
C24 C25 C26 C27 -0.2(3) . . . . ?
C25 C26 C27 C21 -1.0(3) . . . . ?
C27 C21 C23 C24 -1.9(3) . . . . ?
_shelx_SHELXL_version_number 2014/7
_iucr_refine_instructions_details
;
cd0965a.res created by SHELXL-2014/7
TITL cd0965a R = New: P-1
CELL 0.71073 9.1842 10.542 11.953 84.992 72.078 74.256
ZERR 2 0.0015 0.002 0.002 0.011 0.011 0.011
LATT 1
SFAC C Br N O H
UNIT 52 2 4 2 50
L.S. 5
PLAN 5
List 4
BOND
BOND $H
fmap 2
acta
MORE -1
CONF
OMIT -3 55
OMIT 1 -1 5
REM
REM
REM
WGHT 0.040000 0.450000
FVAR 1.07387
BR1 2 0.694115 1.350079 0.515730 11.00000 0.01825 0.02731 =
0.03910 0.01455 -0.01305 -0.01113
O1 4 -0.015902 1.095416 0.715680 11.00000 0.02013 0.02425 =
0.01497 0.00287 -0.00875 -0.01209
N1 3 0.226352 1.038750 0.768071 11.00000 0.01975 0.01558 =
0.02480 0.00629 -0.01196 -0.00741
N2 3 0.054064 1.103747 0.589823 11.00000 0.01756 0.02356 =
0.01539 0.00304 -0.00807 -0.00895
C1 1 0.348876 1.094499 0.706763 11.00000 0.02043 0.01756 =
0.01516 0.00413 -0.01022 -0.00864
C2 1 0.510023 1.033851 0.664989 11.00000 0.02231 0.01452 =
0.02511 0.00411 -0.01238 -0.00348
C3 1 0.612203 1.111719 0.607006 11.00000 0.01404 0.02255 =
0.02347 0.00250 -0.00956 -0.00254
C4 1 0.551654 1.245821 0.593858 11.00000 0.01966 0.01988 =
0.01879 0.00447 -0.01029 -0.00919
C5 1 0.390285 1.307803 0.636567 11.00000 0.01774 0.01548 =
0.01736 0.00184 -0.01004 -0.00540
C6 1 0.289508 1.230554 0.692444 11.00000 0.01633 0.01590 =
0.01273 0.00162 -0.00918 -0.00372
C7 1 0.110036 1.267712 0.744486 11.00000 0.01597 0.01632 =
0.01550 0.00103 -0.00694 -0.00562
C8 1 0.027740 1.324726 0.649851 11.00000 0.01530 0.01628 =
0.01749 0.00100 -0.00819 -0.00274
C9 1 0.068736 1.220755 0.559044 11.00000 0.01383 0.01800 =
0.01760 -0.00062 -0.01018 -0.00309
C10 1 0.073568 1.131770 0.782535 11.00000 0.01746 0.02040 =
0.01576 0.00171 -0.00852 -0.00949
H10 5 0.006917 1.134690 0.860056 11.00000 -1.20000
C11 1 0.245079 0.898125 0.784498 11.00000 0.02413 0.01719 =
0.02610 0.00516 -0.01438 -0.01090
C12 1 0.293855 0.842576 0.893501 11.00000 0.01596 0.01843 =
0.01876 0.00514 -0.00647 -0.00783
C13 1 0.311477 0.707738 0.919643 11.00000 0.01603 0.01885 =
0.02446 0.00423 -0.00640 -0.00567
C14 1 0.354109 0.658009 1.020750 11.00000 0.01978 0.02026 =
0.02846 0.01096 -0.00659 -0.00451
C15 1 0.381605 0.737578 1.094292 11.00000 0.01987 0.03727 =
0.02027 0.00826 -0.00563 -0.00364
C16 1 0.366192 0.870208 1.067069 11.00000 0.02289 0.03199 =
0.02011 -0.00218 -0.00850 -0.00492
C17 1 0.322826 0.922296 0.967411 11.00000 0.02231 0.01902 =
0.02165 0.00181 -0.00848 -0.00632
C18 1 0.285330 0.617890 0.840050 11.00000 0.02698 0.01787 =
0.03799 0.00292 -0.01236 -0.00872
C19 1 0.053116 1.365005 0.846535 11.00000 0.01983 0.01888 =
0.01703 -0.00075 -0.00804 -0.00615
C20 1 0.124363 1.315470 0.947365 11.00000 0.02949 0.02556 =
0.01692 -0.00166 -0.01237 -0.00753
C21 1 0.133293 1.244503 0.431036 11.00000 0.01442 0.01572 =
0.01727 0.00065 -0.00904 -0.00243
C23 1 0.225911 1.334030 0.390518 11.00000 0.02073 0.01852 =
0.01930 0.00031 -0.01169 -0.00457
C24 1 0.292950 1.350288 0.270846 11.00000 0.01934 0.02416 =
0.02160 0.00438 -0.00731 -0.00830
C25 1 0.266875 1.278381 0.189981 11.00000 0.02171 0.02976 =
0.01532 0.00367 -0.00786 -0.00496
C26 1 0.172399 1.190574 0.229971 11.00000 0.02253 0.02494 =
0.01896 -0.00183 -0.01227 -0.00410
C27 1 0.104678 1.174003 0.349469 11.00000 0.01753 0.01855 =
0.01970 0.00118 -0.00971 -0.00539
H8A 5 0.056589 1.408804 0.610965 11.00000 -1.20000
H27 5 0.046827 1.116140 0.374239 11.00000 -1.20000
H3 5 0.721515 1.075045 0.578130 11.00000 -1.20000
H2 5 0.550185 0.945000 0.672917 11.00000 -1.20000
H5 5 0.351221 1.399946 0.625700 11.00000 -1.20000
H23 5 0.240833 1.382929 0.446883 11.00000 -1.20000
H11A 5 0.147284 0.879575 0.788859 11.00000 -1.20000
H19A 5 -0.061566 1.388492 0.874969 11.00000 -1.20000
H18A 5 0.366953 0.610770 0.757323 11.00000 -1.50000
H26 5 0.148022 1.138951 0.175974 11.00000 -1.20000
H20A 5 0.081737 1.234467 0.989690 11.00000 -1.50000
H11B 5 0.320183 0.851251 0.714218 11.00000 -1.20000
H19B 5 0.082305 1.445953 0.813312 11.00000 -1.20000
H20B 5 0.091606 1.382698 1.006272 11.00000 -1.50000
H15 5 0.407535 0.695844 1.168754 11.00000 -1.20000
H25 5 0.317981 1.288072 0.107812 11.00000 -1.20000
H24 5 0.360492 1.408537 0.243344 11.00000 -1.20000
H20C 5 0.244014 1.294306 0.917793 11.00000 -1.50000
H16 5 0.396106 0.925955 1.114593 11.00000 -1.20000
H17 5 0.311083 1.013067 0.947643 11.00000 -1.20000
H14 5 0.369543 0.573315 1.035069 11.00000 -1.20000
H8B 5 -0.085277 1.347674 0.684857 11.00000 -1.20000
H18B 5 0.301998 0.531075 0.870923 11.00000 -1.50000
H18C 5 0.181121 0.646976 0.835875 11.00000 -1.50000
HKLF 4
REM cd0965a R = New: P-1
REM R1 = 0.0377 for 4223 Fo > 4sig(Fo) and 0.0416 for all 4807 data
REM 346 parameters refined using 0 restraints
END
WGHT 0.0543 0.0000
REM Highest difference peak 0.725, deepest hole -0.770, 1-sigma level 0.076
Q1 1 0.6014 1.3765 0.5730 11.00000 0.05 0.72
Q2 1 0.7998 1.3170 0.4570 11.00000 0.05 0.65
Q3 1 0.0930 1.0432 0.5421 11.00000 0.05 0.48
Q4 1 0.5960 1.2974 0.5672 11.00000 0.05 0.45
Q5 1 0.7409 1.2473 0.4577 11.00000 0.05 0.43
REM The information below was added by Olex2.
REM
REM R1 = 0.0377 for 4223 Fo > 4sig(Fo) and 0.0416 for all 15128 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.72, deepest hole -0.77
REM Mean Shift 0, Max Shift 0.002.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0416
REM R1_gt = 0.0377
REM wR_ref = 0.0885
REM GOOF = 1.021
REM Shift_max = 0.002
REM Shift_mean = 0
REM Reflections_all = 15128
REM Reflections_gt = 4223
REM Parameters = n/a
REM Hole = -0.77
REM Peak = 0.72
REM Flack = n/a
;
_olex2_exptl_crystal_mounting_method 'glass fiber'
_olex2_submission_special_instructions 'No special instructions were received'