# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
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data_zz
_audit_block_doi 10.5517/ccdc.csd.cc248w1c
_database_code_depnum_ccdc_archive 'CCDC 1974732'
_audit_update_record
;
2019-12-30 deposited with the CCDC. 2020-02-11 downloaded from the CCDC.
;
_audit_creation_date 2019-12-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2018/3
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C17 H16 Br N O2'
_chemical_formula_sum 'C17 H16 Br N O2'
_chemical_formula_weight 346.22
_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'
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'
_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 15.7754(7)
_cell_length_b 8.5582(4)
_cell_length_c 11.6197(5)
_cell_angle_alpha 90
_cell_angle_beta 107.1620(10)
_cell_angle_gamma 90
_cell_volume 1498.91(12)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 4434
_cell_measurement_temperature 170
_cell_measurement_theta_max 26.383
_cell_measurement_theta_min 2.703
_shelx_estimated_absorpt_T_max 0.898
_shelx_estimated_absorpt_T_min 0.810
_exptl_absorpt_coefficient_mu 2.746
_exptl_absorpt_correction_T_max 0.7454
_exptl_absorpt_correction_T_min 0.5006
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1178 before and 0.0610 after correction. The Ratio of minimum to maximum transmission is 0.6716. The \l/2 correction factor is Not present.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.534
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 704
_exptl_crystal_size_max 0.08
_exptl_crystal_size_mid 0.05
_exptl_crystal_size_min 0.04
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0590
_diffrn_reflns_av_unetI/netI 0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max 19
_diffrn_reflns_limit_h_min -17
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_number 15168
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.398
_diffrn_reflns_theta_min 2.703
_diffrn_ambient_temperature 170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type 'D8 VENTURE'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2379
_reflns_number_total 3036
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT V8.38A (?, 2016)'
_computing_data_collection ?
_computing_data_reduction 'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.335
_refine_diff_density_min -0.433
_refine_diff_density_rms 0.077
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.042
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 192
_refine_ls_number_reflns 3036
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0533
_refine_ls_R_factor_gt 0.0342
_refine_ls_restrained_S_all 1.042
_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^)+(0.0273P)^2^+1.1195P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0695
_refine_ls_wR_factor_ref 0.0784
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups, All N(H) groups
At 1.5 times of:
All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
C1(H1A,H1B), C3(H3A,H3B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
N1(H1), C16(H16), C14(H14), C13(H13), C9(H9), C6(H6)
2.c Idealised Me refined as rotating group:
C11(H11A,H11B,H11C)
2.d Idealised tetrahedral OH refined as rotating group:
O2(H2)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.54564(2) 0.76171(4) 0.33083(3) 0.03097(11) Uani 1 1 d . . . . .
O2 O 0.24076(13) 0.4707(2) 0.24474(16) 0.0255(5) Uani 1 1 d . . . . .
H2 H 0.248830 0.471586 0.176446 0.038 Uiso 1 1 calc GR . . . .
O1 O 0.26543(13) 0.0141(2) 0.52853(16) 0.0258(5) Uani 1 1 d . . . . .
N1 N 0.24527(15) 0.2323(2) 0.41060(19) 0.0199(5) Uani 1 1 d . . . . .
H1 H 0.250964 0.268954 0.342513 0.024 Uiso 1 1 calc R . . . .
C16 C 0.38062(18) 0.6046(3) 0.2911(2) 0.0194(6) Uani 1 1 d . . . . .
H16 H 0.380774 0.599280 0.209494 0.023 Uiso 1 1 calc R . . . .
C15 C 0.45000(18) 0.6740(3) 0.3774(2) 0.0199(6) Uani 1 1 d . . . . .
C14 C 0.45178(19) 0.6841(3) 0.4968(2) 0.0221(6) Uani 1 1 d . . . . .
H14 H 0.500474 0.730802 0.555201 0.027 Uiso 1 1 calc R . . . .
C17 C 0.31060(18) 0.5427(3) 0.3262(2) 0.0188(6) Uani 1 1 d . . . . .
C12 C 0.30880(18) 0.5520(3) 0.4459(2) 0.0191(6) Uani 1 1 d . . . . .
C10 C 0.27333(18) 0.0848(3) 0.4394(2) 0.0203(6) Uani 1 1 d . . . . .
C7 C 0.20729(18) 0.3357(3) 0.4783(2) 0.0183(6) Uani 1 1 d . . . . .
C13 C 0.38081(18) 0.6243(3) 0.5286(2) 0.0211(6) Uani 1 1 d . . . . .
H13 H 0.380799 0.632584 0.610087 0.025 Uiso 1 1 calc R . . . .
C9 C 0.19603(19) 0.5950(3) 0.5534(2) 0.0227(6) Uani 1 1 d . . . . .
H9 H 0.212066 0.702357 0.559763 0.027 Uiso 1 1 calc R . . . .
C8 C 0.23470(18) 0.4928(3) 0.4895(2) 0.0191(6) Uani 1 1 d . . . . .
C5 C 0.11006(18) 0.3844(3) 0.5986(2) 0.0236(6) Uani 1 1 d . . . . .
C6 C 0.14510(18) 0.2817(3) 0.5320(2) 0.0210(6) Uani 1 1 d . . . . .
H6 H 0.126688 0.175586 0.523283 0.025 Uiso 1 1 calc R . . . .
C4 C 0.13414(19) 0.5400(3) 0.6077(2) 0.0243(6) Uani 1 1 d . . . . .
C11 C 0.3190(2) 0.0106(3) 0.3571(2) 0.0274(7) Uani 1 1 d . . . . .
H11A H 0.383253 0.010531 0.395940 0.041 Uiso 1 1 calc GR . . . .
H11B H 0.305597 0.069925 0.281720 0.041 Uiso 1 1 calc GR . . . .
H11C H 0.298111 -0.097123 0.339847 0.041 Uiso 1 1 calc GR . . . .
C1 C 0.0450(2) 0.3493(3) 0.6673(3) 0.0295(7) Uani 1 1 d . . . . .
H1A H 0.067965 0.266255 0.727851 0.035 Uiso 1 1 calc R . . . .
H1B H -0.012770 0.315575 0.612187 0.035 Uiso 1 1 calc R . . . .
C3 C 0.0863(2) 0.6288(4) 0.6828(3) 0.0332(7) Uani 1 1 d . . . . .
H3A H 0.045036 0.706835 0.633253 0.040 Uiso 1 1 calc R . . . .
H3B H 0.129012 0.682881 0.750888 0.040 Uiso 1 1 calc R . . . .
C2 C 0.0359(3) 0.5031(4) 0.7279(4) 0.0522(11) Uani 1 1 d . . . . .
H2A H 0.060298 0.492423 0.816414 0.063 Uiso 1 1 calc R . . . .
H2B H -0.027493 0.532118 0.708732 0.063 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
Br1 0.02550(18) 0.04302(19) 0.02472(16) 0.00422(13) 0.00793(12) -0.00966(14)
O2 0.0293(12) 0.0319(11) 0.0151(9) -0.0015(8) 0.0063(9) -0.0105(9)
O1 0.0370(13) 0.0236(10) 0.0190(10) 0.0043(8) 0.0116(9) 0.0039(9)
N1 0.0255(13) 0.0180(11) 0.0180(11) 0.0011(9) 0.0095(10) 0.0013(9)
C16 0.0272(16) 0.0190(13) 0.0132(12) 0.0005(10) 0.0079(12) 0.0012(11)
C15 0.0213(15) 0.0187(13) 0.0218(13) 0.0023(11) 0.0094(12) 0.0006(11)
C14 0.0257(16) 0.0216(14) 0.0168(13) -0.0001(11) 0.0028(12) -0.0034(12)
C17 0.0237(15) 0.0157(13) 0.0155(12) -0.0006(10) 0.0031(12) 0.0000(11)
C12 0.0251(16) 0.0156(12) 0.0177(13) 0.0005(10) 0.0082(12) 0.0038(11)
C10 0.0215(16) 0.0202(14) 0.0182(13) -0.0020(10) 0.0045(12) 0.0009(11)
C7 0.0193(15) 0.0181(13) 0.0163(13) 0.0010(10) 0.0037(11) 0.0035(11)
C13 0.0287(17) 0.0185(13) 0.0158(13) -0.0013(10) 0.0060(12) 0.0019(11)
C9 0.0270(16) 0.0200(14) 0.0220(14) -0.0006(11) 0.0087(12) 0.0006(12)
C8 0.0195(15) 0.0206(13) 0.0157(13) 0.0007(10) 0.0029(11) 0.0007(11)
C5 0.0195(16) 0.0293(15) 0.0226(14) 0.0071(11) 0.0073(12) 0.0055(12)
C6 0.0194(15) 0.0196(14) 0.0247(14) 0.0027(10) 0.0077(12) 0.0021(11)
C4 0.0243(16) 0.0271(15) 0.0223(14) -0.0002(11) 0.0083(12) 0.0060(12)
C11 0.0338(18) 0.0239(15) 0.0272(15) -0.0018(12) 0.0131(14) 0.0037(13)
C1 0.0249(17) 0.0354(17) 0.0325(16) 0.0041(13) 0.0148(14) 0.0040(13)
C3 0.0319(19) 0.0375(18) 0.0351(17) -0.0061(13) 0.0173(15) 0.0064(14)
C2 0.073(3) 0.039(2) 0.066(3) 0.0080(17) 0.055(2) 0.0139(18)
_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 C15 1.901(3) . ?
O2 C17 1.369(3) . ?
O1 C10 1.237(3) . ?
N1 C10 1.346(3) . ?
N1 C7 1.428(3) . ?
C16 C15 1.382(4) . ?
C16 C17 1.390(4) . ?
C15 C14 1.382(4) . ?
C14 C13 1.376(4) . ?
C17 C12 1.402(3) . ?
C12 C13 1.397(4) . ?
C12 C8 1.493(4) . ?
C10 C11 1.498(4) . ?
C7 C8 1.406(4) . ?
C7 C6 1.388(4) . ?
C9 C8 1.399(4) . ?
C9 C4 1.391(4) . ?
C5 C6 1.389(4) . ?
C5 C4 1.380(4) . ?
C5 C1 1.504(4) . ?
C4 C3 1.515(4) . ?
C1 C2 1.520(4) . ?
C3 C2 1.520(4) . ?
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 N1 C7 127.2(2) . . ?
C15 C16 C17 118.6(2) . . ?
C16 C15 Br1 119.2(2) . . ?
C16 C15 C14 122.2(2) . . ?
C14 C15 Br1 118.6(2) . . ?
C13 C14 C15 117.9(3) . . ?
O2 C17 C16 121.1(2) . . ?
O2 C17 C12 117.6(2) . . ?
C16 C17 C12 121.3(2) . . ?
C17 C12 C8 124.4(2) . . ?
C13 C12 C17 117.2(2) . . ?
C13 C12 C8 118.4(2) . . ?
O1 C10 N1 124.1(2) . . ?
O1 C10 C11 120.9(2) . . ?
N1 C10 C11 115.0(2) . . ?
C8 C7 N1 118.5(2) . . ?
C6 C7 N1 120.5(2) . . ?
C6 C7 C8 121.0(2) . . ?
C14 C13 C12 122.8(2) . . ?
C4 C9 C8 120.2(2) . . ?
C7 C8 C12 122.9(2) . . ?
C9 C8 C12 118.4(2) . . ?
C9 C8 C7 118.5(2) . . ?
C6 C5 C1 127.9(3) . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 C1 111.6(2) . . ?
C7 C6 C5 119.4(2) . . ?
C9 C4 C3 128.8(3) . . ?
C5 C4 C9 120.4(2) . . ?
C5 C4 C3 110.8(2) . . ?
C5 C1 C2 104.2(2) . . ?
C4 C3 C2 104.1(2) . . ?
C1 C2 C3 108.8(2) . . ?
_iucr_refine_instructions_details
;
TITL zz_a.res in P2(1)/c
zz.res
created by SHELXL-2018/3 at 10:39:23 on 26-Dec-2019
REM Old TITL zz in P2(1)/c
REM SHELXT solution in P2(1)/c
REM R1 0.132, Rweak 0.005, Alpha 0.037, Orientation as input
REM Formula found by SHELXT: C17 N O2 Br
CELL 0.71073 15.7754 8.5582 11.6197 90 107.162 90
ZERR 4 0.0007 0.0004 0.0005 0 0.001 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Br N O
UNIT 68 64 4 4 8
L.S. 4 0 67
PLAN 20
SIZE 0.08 0.05 0.04
TEMP -103.15
list 4
fmap 2 53
ACTA
REM
REM
REM
WGHT 0.027300 1.119500
FVAR 0.57220
BR1 3 0.545638 0.761709 0.330830 11.00000 0.02550 0.04302 =
0.02472 0.00422 0.00793 -0.00966
O2 5 0.240762 0.470668 0.244740 11.00000 0.02928 0.03190 =
0.01511 -0.00154 0.00626 -0.01048
AFIX 147
H2 2 0.248830 0.471586 0.176446 11.00000 -1.50000
AFIX 0
O1 5 0.265426 0.014058 0.528529 11.00000 0.03697 0.02360 =
0.01902 0.00427 0.01165 0.00387
N1 4 0.245270 0.232284 0.410599 11.00000 0.02554 0.01801 =
0.01805 0.00106 0.00945 0.00132
AFIX 43
H1 2 0.250964 0.268954 0.342513 11.00000 -1.20000
AFIX 0
C16 1 0.380623 0.604589 0.291098 11.00000 0.02720 0.01904 =
0.01321 0.00053 0.00787 0.00122
AFIX 43
H16 2 0.380774 0.599280 0.209494 11.00000 -1.20000
AFIX 0
C15 1 0.449999 0.674017 0.377428 11.00000 0.02128 0.01867 =
0.02185 0.00227 0.00943 0.00063
C14 1 0.451777 0.684082 0.496835 11.00000 0.02573 0.02157 =
0.01683 -0.00007 0.00279 -0.00344
AFIX 43
H14 2 0.500474 0.730802 0.555201 11.00000 -1.20000
AFIX 0
C17 1 0.310597 0.542668 0.326156 11.00000 0.02370 0.01567 =
0.01545 -0.00058 0.00310 -0.00003
C12 1 0.308804 0.552029 0.445911 11.00000 0.02512 0.01558 =
0.01771 0.00045 0.00823 0.00384
C10 1 0.273333 0.084846 0.439422 11.00000 0.02155 0.02018 =
0.01819 -0.00199 0.00451 0.00086
C7 1 0.207294 0.335739 0.478251 11.00000 0.01933 0.01814 =
0.01634 0.00103 0.00373 0.00351
C13 1 0.380815 0.624325 0.528562 11.00000 0.02869 0.01852 =
0.01576 -0.00133 0.00605 0.00195
AFIX 43
H13 2 0.380799 0.632584 0.610087 11.00000 -1.20000
AFIX 0
C9 1 0.196027 0.595007 0.553415 11.00000 0.02697 0.01999 =
0.02198 -0.00061 0.00874 0.00060
AFIX 43
H9 2 0.212066 0.702357 0.559763 11.00000 -1.20000
AFIX 0
C8 1 0.234703 0.492796 0.489518 11.00000 0.01949 0.02063 =
0.01574 0.00070 0.00288 0.00073
C5 1 0.110061 0.384416 0.598621 11.00000 0.01951 0.02927 =
0.02265 0.00715 0.00733 0.00548
C6 1 0.145101 0.281732 0.531992 11.00000 0.01941 0.01963 =
0.02465 0.00271 0.00765 0.00210
AFIX 43
H6 2 0.126688 0.175586 0.523283 11.00000 -1.20000
AFIX 0
C4 1 0.134143 0.540038 0.607724 11.00000 0.02428 0.02713 =
0.02234 -0.00022 0.00825 0.00604
C11 1 0.319024 0.010628 0.357116 11.00000 0.03377 0.02389 =
0.02717 -0.00181 0.01315 0.00375
AFIX 137
H11A 2 0.383253 0.010531 0.395940 11.00000 -1.50000
H11B 2 0.305597 0.069925 0.281720 11.00000 -1.50000
H11C 2 0.298111 -0.097123 0.339847 11.00000 -1.50000
AFIX 0
C1 1 0.045028 0.349257 0.667315 11.00000 0.02485 0.03539 =
0.03247 0.00412 0.01483 0.00396
AFIX 23
H1A 2 0.067965 0.266255 0.727851 11.00000 -1.20000
H1B 2 -0.012770 0.315575 0.612187 11.00000 -1.20000
AFIX 0
C3 1 0.086290 0.628773 0.682787 11.00000 0.03191 0.03746 =
0.03508 -0.00610 0.01725 0.00643
AFIX 23
H3A 2 0.045036 0.706835 0.633253 11.00000 -1.20000
H3B 2 0.129012 0.682881 0.750888 11.00000 -1.20000
AFIX 0
C2 1 0.035900 0.503055 0.727925 11.00000 0.07326 0.03949 =
0.06602 0.00800 0.05473 0.01395
AFIX 23
H2A 2 0.060298 0.492423 0.816414 11.00000 -1.20000
H2B 2 -0.027493 0.532118 0.708732 11.00000 -1.20000
AFIX 0
HKLF 4
REM zz_a.res in P2(1)/c
REM wR2 = 0.0784, GooF = S = 1.042, Restrained GooF = 1.042 for all data
REM R1 = 0.0342 for 2379 Fo > 4sig(Fo) and 0.0533 for all 3036 data
REM 192 parameters refined using 0 restraints
END
WGHT 0.0254 1.1351
REM Highest difference peak 0.335, deepest hole -0.433, 1-sigma level 0.077
Q1 1 0.0008 0.5117 0.7836 11.00000 0.05 0.33
Q2 1 0.1429 0.5684 0.5581 11.00000 0.05 0.33
Q3 1 0.3422 0.5967 0.4786 11.00000 0.05 0.30
Q4 1 0.5005 0.4926 0.2467 11.00000 0.05 0.30
Q5 1 0.0191 0.2663 0.6743 11.00000 0.05 0.28
Q6 1 0.2054 0.2826 0.5358 11.00000 0.05 0.27
Q7 1 0.2750 0.5256 0.4621 11.00000 0.05 0.26
Q8 1 0.4428 -0.0385 0.4407 11.00000 0.05 0.26
Q9 1 0.4296 0.7078 0.4307 11.00000 0.05 0.25
Q10 1 0.4166 0.5872 0.3529 11.00000 0.05 0.25
Q11 1 0.0980 0.1638 0.4794 11.00000 0.05 0.25
Q12 1 0.2755 0.7592 0.5694 11.00000 0.05 0.25
Q13 1 0.2864 0.2654 0.3844 11.00000 0.05 0.24
Q14 1 0.2785 0.1725 0.4450 11.00000 0.05 0.24
Q15 1 0.0987 0.7691 0.7061 11.00000 0.05 0.24
Q16 1 0.4767 0.5065 0.3771 11.00000 0.05 0.24
Q17 1 0.1349 0.5801 0.6654 11.00000 0.05 0.24
Q18 1 0.3347 0.6192 0.3026 11.00000 0.05 0.24
Q19 1 0.3660 0.5622 0.1159 11.00000 0.05 0.23
Q20 1 0.3196 0.2526 0.5465 11.00000 0.05 0.23
REM The information below was added by Olex2.
REM
REM R1 = 0.0342 for 2379 Fo > 4sig(Fo) and 0.0533 for all 15602 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.33, deepest hole -0.43
REM Mean Shift 0, Max Shift 0.001.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0533
REM R1_gt = 0.0342
REM wR_ref = 0.0784
REM GOOF = 1.042
REM Shift_max = 0.001
REM Shift_mean = 0
REM Reflections_all = 15602
REM Reflections_gt = 2379
REM Parameters = n/a
REM Hole = -0.43
REM Peak = 0.33
REM Flack = n/a
;
_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_220191293lxj_0m
_audit_block_doi 10.5517/ccdc.csd.cc248w2d
_database_code_depnum_ccdc_archive 'CCDC 1974733'
_audit_update_record
;
2019-12-30 deposited with the CCDC. 2020-02-11 downloaded from the CCDC.
;
_audit_creation_date 2019-12-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2018/3
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C20 H14 Br N O3'
_chemical_formula_sum 'C20 H14 Br N O3'
_chemical_formula_weight 396.23
_chemical_absolute_configuration .
_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'
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'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system orthorhombic
_space_group_IT_number 19
_space_group_name_H-M_alt 'P 21 21 21'
_space_group_name_Hall 'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a 4.2743(5)
_cell_length_b 15.4368(16)
_cell_length_c 24.939(3)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 1645.5(3)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 2045
_cell_measurement_temperature 170
_cell_measurement_theta_max 24.512
_cell_measurement_theta_min 2.370
_shelx_estimated_absorpt_T_max 0.951
_shelx_estimated_absorpt_T_min 0.704
_exptl_absorpt_coefficient_mu 2.517
_exptl_absorpt_correction_T_max 0.7454
_exptl_absorpt_correction_T_min 0.4853
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1429 before and 0.0772 after correction. The Ratio of minimum to maximum transmission is 0.6511. The \l/2 correction factor is Not present.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.599
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description needle
_exptl_crystal_F_000 800
_exptl_crystal_size_max 0.15
_exptl_crystal_size_mid 0.03
_exptl_crystal_size_min 0.02
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0614
_diffrn_reflns_av_unetI/netI 0.1007
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max 5
_diffrn_reflns_limit_h_min -4
_diffrn_reflns_limit_k_max 19
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_l_max 30
_diffrn_reflns_limit_l_min -22
_diffrn_reflns_number 7712
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.506
_diffrn_reflns_theta_min 2.639
_diffrn_ambient_temperature 170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type 'D8 VENTURE'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.650
_reflns_Friedel_fraction_full 0.975
_reflns_Friedel_fraction_max 0.952
_reflns_number_gt 2289
_reflns_number_total 3328
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT V8.38A (?, 2016)'
_computing_data_collection ?
_computing_data_reduction 'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.405
_refine_diff_density_min -0.631
_refine_diff_density_rms 0.100
_refine_ls_abs_structure_details
;
Flack x determined using 668 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack 0.194(12)
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.997
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 228
_refine_ls_number_reflns 3328
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0980
_refine_ls_R_factor_gt 0.0513
_refine_ls_restrained_S_all 0.997
_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^)+(0.0487P)^2^+0.2479P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0967
_refine_ls_wR_factor_ref 0.1169
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All N(H) groups
At 1.5 times of:
All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
N1(H1A), C17(H17), C19(H19), C11(H11), C20(H20), C12(H12), C5(H5), C4(H4),
C3(H3), C2(H2)
2.b Idealised Me refined as rotating group:
C13(H13A,H13B,H13C)
2.c Idealised tetrahedral OH refined as rotating group:
O1(H1)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.5354(2) 0.01814(5) 0.67719(3) 0.0368(3) Uani 1 1 d . . . . .
O3 O 0.3930(13) 0.5933(3) 0.5734(2) 0.0266(13) Uani 1 1 d . . . . .
O1 O -0.0278(14) 0.2776(3) 0.5844(2) 0.0288(12) Uani 1 1 d . . . . .
H1 H -0.018341 0.242086 0.558901 0.043 Uiso 1 1 calc GR . . . .
O2 O 0.5291(15) 0.3403(3) 0.4927(2) 0.0365(14) Uani 1 1 d . . . . .
N1 N 0.4814(17) 0.4056(3) 0.5718(2) 0.0249(14) Uani 1 1 d . . . . .
H1A H 0.660143 0.382247 0.581692 0.030 Uiso 1 1 calc R . . . .
C18 C 0.4122(15) 0.1363(4) 0.6736(3) 0.0221(16) Uani 1 1 d . . . . .
C9 C 0.3098(18) 0.4499(5) 0.6120(3) 0.0228(18) Uani 1 1 d . . . . .
C17 C 0.2349(17) 0.1628(4) 0.6305(3) 0.0214(17) Uani 1 1 d . . . . .
H17 H 0.166324 0.122046 0.604465 0.026 Uiso 1 1 calc R . . . .
C8 C 0.2721(17) 0.5384(5) 0.6125(3) 0.0231(18) Uani 1 1 d . . . . .
C19 C 0.513(2) 0.1940(4) 0.7125(3) 0.0263(16) Uani 1 1 d . . . . .
H19 H 0.633311 0.174684 0.742169 0.032 Uiso 1 1 calc R . . . .
C11 C 0.036(2) 0.4497(4) 0.6978(3) 0.0261(18) Uani 1 1 d . . . . .
H11 H -0.039449 0.418590 0.728077 0.031 Uiso 1 1 calc R . . . .
C7 C 0.107(2) 0.5840(5) 0.6522(3) 0.026(2) Uani 1 1 d . . . . .
C20 C 0.4329(19) 0.2799(4) 0.7070(3) 0.0267(18) Uani 1 1 d . . . . .
H20 H 0.498349 0.319882 0.733734 0.032 Uiso 1 1 calc R . . . .
C16 C 0.1579(16) 0.2495(5) 0.6255(3) 0.0238(18) Uani 1 1 d . . . . .
C10 C 0.1940(17) 0.4044(4) 0.6573(3) 0.0221(19) Uani 1 1 d . . . . .
C15 C 0.2586(16) 0.3102(4) 0.6635(3) 0.0203(18) Uani 1 1 d . . . . .
C12 C -0.0143(19) 0.5384(4) 0.6952(3) 0.0261(17) Uani 1 1 d . . . . .
H12 H -0.129874 0.567274 0.722345 0.031 Uiso 1 1 calc R . . . .
C14 C 0.3974(18) 0.3956(5) 0.5196(3) 0.028(2) Uani 1 1 d . . . . .
C1 C 0.3048(19) 0.6757(5) 0.5897(3) 0.0287(19) Uani 1 1 d . . . . .
C5 C 0.023(2) 0.7523(5) 0.6582(3) 0.038(2) Uani 1 1 d . . . . .
H5 H -0.094467 0.752861 0.690498 0.045 Uiso 1 1 calc R . . . .
C6 C 0.1280(19) 0.6748(5) 0.6367(4) 0.034(2) Uani 1 1 d . . . . .
C4 C 0.091(2) 0.8282(5) 0.6320(4) 0.043(2) Uani 1 1 d . . . . .
H4 H 0.015921 0.881497 0.645990 0.051 Uiso 1 1 calc R . . . .
C3 C 0.271(2) 0.8283(6) 0.5846(4) 0.044(2) Uani 1 1 d . . . . .
H3 H 0.318841 0.881679 0.567509 0.052 Uiso 1 1 calc R . . . .
C2 C 0.380(2) 0.7512(5) 0.5624(4) 0.036(2) Uani 1 1 d . . . . .
H2 H 0.500240 0.750312 0.530357 0.043 Uiso 1 1 calc R . . . .
C13 C 0.163(2) 0.4555(5) 0.4959(3) 0.038(2) Uani 1 1 d . . . . .
H13A H 0.268637 0.508045 0.483243 0.057 Uiso 1 1 calc GR . . . .
H13B H 0.007509 0.470933 0.523081 0.057 Uiso 1 1 calc GR . . . .
H13C H 0.059091 0.426974 0.465643 0.057 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
Br1 0.0465(5) 0.0233(3) 0.0406(5) 0.0028(4) -0.0023(5) 0.0054(4)
O3 0.035(3) 0.020(3) 0.025(3) 0.001(2) 0.005(2) 0.003(2)
O1 0.037(3) 0.025(3) 0.024(3) -0.010(2) -0.010(3) 0.004(3)
O2 0.041(3) 0.037(3) 0.032(3) -0.016(2) 0.004(3) 0.005(3)
N1 0.029(4) 0.028(3) 0.018(4) -0.009(2) -0.003(4) -0.001(3)
C18 0.021(4) 0.022(3) 0.024(4) 0.005(3) 0.008(4) 0.004(3)
C9 0.027(4) 0.023(4) 0.019(5) -0.002(3) -0.002(3) -0.007(3)
C17 0.024(4) 0.022(4) 0.018(5) -0.002(3) 0.002(3) -0.001(3)
C8 0.026(4) 0.025(4) 0.018(5) -0.001(3) -0.001(3) 0.001(3)
C19 0.029(4) 0.028(4) 0.023(4) 0.005(3) -0.002(4) -0.002(4)
C11 0.035(4) 0.023(3) 0.020(4) -0.006(3) 0.008(4) -0.002(4)
C7 0.036(5) 0.024(4) 0.019(5) -0.005(3) -0.004(4) -0.001(4)
C20 0.033(4) 0.026(4) 0.020(4) -0.002(3) -0.003(4) -0.001(4)
C16 0.022(4) 0.028(4) 0.021(5) 0.002(4) -0.007(3) 0.003(3)
C10 0.024(4) 0.018(4) 0.024(5) 0.000(3) -0.001(3) 0.003(3)
C15 0.017(3) 0.017(4) 0.027(5) -0.001(3) 0.001(3) -0.005(3)
C12 0.028(4) 0.025(4) 0.026(4) -0.010(3) 0.007(4) 0.002(4)
C14 0.031(5) 0.031(4) 0.021(5) 0.000(4) 0.003(4) -0.005(4)
C1 0.033(4) 0.021(4) 0.032(5) -0.004(4) -0.007(4) 0.009(4)
C5 0.049(5) 0.028(4) 0.037(5) -0.007(3) 0.007(5) 0.001(5)
C6 0.040(5) 0.029(4) 0.032(6) -0.005(4) -0.001(4) 0.003(4)
C4 0.043(6) 0.026(4) 0.058(7) -0.004(4) -0.001(5) 0.004(4)
C3 0.049(6) 0.027(5) 0.054(7) 0.007(4) -0.013(5) -0.005(4)
C2 0.049(6) 0.022(4) 0.037(6) 0.004(4) -0.003(4) -0.001(4)
C13 0.041(5) 0.047(5) 0.026(5) -0.001(4) -0.007(4) -0.010(4)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C18 1.901(6) . ?
O3 C8 1.392(9) . ?
O3 C1 1.387(8) . ?
O1 H1 0.8400 . ?
O1 C16 1.368(8) . ?
O2 C14 1.223(9) . ?
N1 H1A 0.8800 . ?
N1 C9 1.417(9) . ?
N1 C14 1.360(9) . ?
C18 C17 1.377(10) . ?
C18 C19 1.385(10) . ?
C9 C8 1.376(10) . ?
C9 C10 1.419(11) . ?
C17 H17 0.9500 . ?
C17 C16 1.384(10) . ?
C8 C7 1.404(10) . ?
C19 H19 0.9500 . ?
C19 C20 1.377(9) . ?
C11 H11 0.9500 . ?
C11 C10 1.402(10) . ?
C11 C12 1.388(9) . ?
C7 C12 1.384(10) . ?
C7 C6 1.457(10) . ?
C20 H20 0.9500 . ?
C20 C15 1.398(10) . ?
C16 C15 1.400(10) . ?
C10 C15 1.488(9) . ?
C12 H12 0.9500 . ?
C14 C13 1.485(11) . ?
C1 C6 1.395(12) . ?
C1 C2 1.387(11) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(10) . ?
C5 C4 1.373(11) . ?
C4 H4 0.9500 . ?
C4 C3 1.411(13) . ?
C3 H3 0.9500 . ?
C3 C2 1.392(12) . ?
C2 H2 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O3 C8 104.6(6) . . ?
C16 O1 H1 109.5 . . ?
C9 N1 H1A 116.7 . . ?
C14 N1 H1A 116.7 . . ?
C14 N1 C9 126.5(7) . . ?
C17 C18 Br1 118.3(6) . . ?
C17 C18 C19 121.8(6) . . ?
C19 C18 Br1 119.8(6) . . ?
N1 C9 C10 120.3(6) . . ?
C8 C9 N1 123.1(7) . . ?
C8 C9 C10 116.3(7) . . ?
C18 C17 H17 120.4 . . ?
C18 C17 C16 119.2(7) . . ?
C16 C17 H17 120.4 . . ?
O3 C8 C7 112.0(6) . . ?
C9 C8 O3 123.7(7) . . ?
C9 C8 C7 124.3(7) . . ?
C18 C19 H19 120.9 . . ?
C20 C19 C18 118.2(7) . . ?
C20 C19 H19 120.9 . . ?
C10 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C12 C11 C10 122.1(7) . . ?
C8 C7 C6 105.4(7) . . ?
C12 C7 C8 118.6(7) . . ?
C12 C7 C6 135.8(7) . . ?
C19 C20 H20 118.9 . . ?
C19 C20 C15 122.1(7) . . ?
C15 C20 H20 118.9 . . ?
O1 C16 C17 120.7(7) . . ?
O1 C16 C15 118.3(7) . . ?
C17 C16 C15 120.9(7) . . ?
C9 C10 C15 120.0(7) . . ?
C11 C10 C9 119.7(6) . . ?
C11 C10 C15 120.1(7) . . ?
C20 C15 C16 117.7(6) . . ?
C20 C15 C10 120.4(6) . . ?
C16 C15 C10 121.8(7) . . ?
C11 C12 H12 120.6 . . ?
C7 C12 C11 118.8(7) . . ?
C7 C12 H12 120.6 . . ?
O2 C14 N1 118.9(7) . . ?
O2 C14 C13 121.7(8) . . ?
N1 C14 C13 119.3(7) . . ?
O3 C1 C6 112.6(7) . . ?
O3 C1 C2 124.3(8) . . ?
C2 C1 C6 123.1(8) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.0(8) . . ?
C1 C6 C7 105.3(7) . . ?
C5 C6 C7 135.1(8) . . ?
C5 C6 C1 119.5(8) . . ?
C5 C4 H4 119.5 . . ?
C5 C4 C3 121.0(8) . . ?
C3 C4 H4 119.5 . . ?
C4 C3 H3 119.5 . . ?
C2 C3 C4 121.0(8) . . ?
C2 C3 H3 119.5 . . ?
C1 C2 C3 116.5(9) . . ?
C1 C2 H2 121.8 . . ?
C3 C2 H2 121.8 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
_iucr_refine_instructions_details
;
TITL 220191293lxj_0m_a.res in P2(1)2(1)2(1)
220191293lxj_0m.res
created by SHELXL-2018/3 at 12:59:02 on 27-Dec-2019
REM Old TITL 220191293LXJ_0m in P2(1)2(1)2(1)
REM SHELXT solution in P2(1)2(1)2(1)
REM R1 0.131, Rweak 0.028, Alpha 0.004, Orientation as input
REM Flack x = 0.205 ( 0.012 ) from Parsons' quotients
REM Formula found by SHELXT: C20 N O3 Br
CELL 0.71073 4.2743 15.4368 24.9392 90 90 90
ZERR 4 0.0005 0.0016 0.0031 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H Br N O
UNIT 80 56 4 4 12
L.S. 4
PLAN 20
SIZE 0.15 0.03 0.02
TEMP -103.15
BOND $H
list 4
fmap 2
ACTA
REM
REM
REM
WGHT 0.048700 0.247900
FVAR 0.56155
BR1 3 0.535438 0.018144 0.677188 11.00000 0.04651 0.02331 =
0.04061 0.00283 -0.00230 0.00541
O3 5 0.392996 0.593320 0.573392 11.00000 0.03452 0.01982 =
0.02533 0.00075 0.00521 0.00270
O1 5 -0.027757 0.277580 0.584380 11.00000 0.03707 0.02498 =
0.02424 -0.00982 -0.01027 0.00369
AFIX 147
H1 2 -0.018341 0.242086 0.558901 11.00000 -1.50000
AFIX 0
O2 5 0.529103 0.340338 0.492689 11.00000 0.04100 0.03677 =
0.03180 -0.01574 0.00376 0.00501
N1 4 0.481360 0.405616 0.571845 11.00000 0.02865 0.02822 =
0.01791 -0.00911 -0.00253 -0.00052
AFIX 43
H1A 2 0.660143 0.382247 0.581692 11.00000 -1.20000
AFIX 0
C18 1 0.412230 0.136313 0.673550 11.00000 0.02055 0.02205 =
0.02380 0.00531 0.00807 0.00448
C9 1 0.309755 0.449860 0.611988 11.00000 0.02661 0.02253 =
0.01937 -0.00210 -0.00212 -0.00682
C17 1 0.234927 0.162793 0.630478 11.00000 0.02368 0.02217 =
0.01828 -0.00169 0.00238 -0.00070
AFIX 43
H17 2 0.166324 0.122046 0.604465 11.00000 -1.20000
AFIX 0
C8 1 0.272129 0.538377 0.612512 11.00000 0.02568 0.02544 =
0.01833 -0.00149 -0.00113 0.00065
C19 1 0.512620 0.193956 0.712489 11.00000 0.02854 0.02781 =
0.02270 0.00548 -0.00155 -0.00155
AFIX 43
H19 2 0.633311 0.174684 0.742169 11.00000 -1.20000
AFIX 0
C11 1 0.035820 0.449658 0.697831 11.00000 0.03512 0.02285 =
0.02043 -0.00639 0.00777 -0.00197
AFIX 43
H11 2 -0.039449 0.418590 0.728077 11.00000 -1.20000
AFIX 0
C7 1 0.107165 0.583974 0.652161 11.00000 0.03592 0.02409 =
0.01941 -0.00465 -0.00361 -0.00116
C20 1 0.432866 0.279901 0.707038 11.00000 0.03327 0.02631 =
0.02049 -0.00165 -0.00348 -0.00141
AFIX 43
H20 2 0.498349 0.319882 0.733734 11.00000 -1.20000
AFIX 0
C16 1 0.157851 0.249516 0.625541 11.00000 0.02172 0.02849 =
0.02116 0.00212 -0.00746 0.00284
C10 1 0.194022 0.404403 0.657313 11.00000 0.02436 0.01772 =
0.02435 0.00014 -0.00105 0.00314
C15 1 0.258610 0.310232 0.663481 11.00000 0.01692 0.01728 =
0.02658 -0.00058 0.00113 -0.00510
C12 1 -0.014318 0.538382 0.695161 11.00000 0.02753 0.02459 =
0.02629 -0.01011 0.00674 0.00204
AFIX 43
H12 2 -0.129874 0.567274 0.722345 11.00000 -1.20000
AFIX 0
C14 1 0.397385 0.395647 0.519597 11.00000 0.03095 0.03128 =
0.02112 -0.00048 0.00309 -0.00493
C1 1 0.304800 0.675691 0.589686 11.00000 0.03327 0.02086 =
0.03209 -0.00413 -0.00662 0.00897
C5 1 0.022979 0.752274 0.658160 11.00000 0.04861 0.02806 =
0.03650 -0.00698 0.00687 0.00080
AFIX 43
H5 2 -0.094467 0.752861 0.690498 11.00000 -1.20000
AFIX 0
C6 1 0.128047 0.674843 0.636702 11.00000 0.03989 0.02929 =
0.03207 -0.00522 -0.00147 0.00341
C4 1 0.091164 0.828199 0.631977 11.00000 0.04324 0.02641 =
0.05828 -0.00406 -0.00112 0.00408
AFIX 43
H4 2 0.015921 0.881497 0.645990 11.00000 -1.20000
AFIX 0
C3 1 0.271291 0.828256 0.584572 11.00000 0.04931 0.02725 =
0.05405 0.00745 -0.01320 -0.00493
AFIX 43
H3 2 0.318841 0.881679 0.567509 11.00000 -1.20000
AFIX 0
C2 1 0.380384 0.751170 0.562431 11.00000 0.04903 0.02222 =
0.03694 0.00415 -0.00345 -0.00066
AFIX 43
H2 2 0.500240 0.750312 0.530357 11.00000 -1.20000
AFIX 0
C13 1 0.163254 0.455486 0.495875 11.00000 0.04061 0.04716 =
0.02619 -0.00091 -0.00710 -0.01047
AFIX 137
H13A 2 0.268637 0.508045 0.483243 11.00000 -1.50000
H13B 2 0.007509 0.470933 0.523081 11.00000 -1.50000
H13C 2 0.059091 0.426974 0.465643 11.00000 -1.50000
AFIX 0
HKLF 4
REM 220191293lxj_0m_a.res in P2(1)2(1)2(1)
REM wR2 = 0.1169, GooF = S = 0.997, Restrained GooF = 0.997 for all data
REM R1 = 0.0513 for 2289 Fo > 4sig(Fo) and 0.0980 for all 3328 data
REM 228 parameters refined using 0 restraints
END
WGHT 0.0328 0.8011
REM Highest difference peak 0.405, deepest hole -0.631, 1-sigma level 0.100
Q1 1 0.2586 0.0614 0.6679 11.00000 0.05 0.40
Q2 1 0.3478 -0.0190 0.7172 11.00000 0.05 0.39
Q3 1 -0.5360 0.5424 0.7191 11.00000 0.05 0.39
Q4 1 0.8284 0.0223 0.7110 11.00000 0.05 0.37
Q5 1 0.0414 0.9848 0.6321 11.00000 0.05 0.37
Q6 1 -0.2373 0.5742 0.6534 11.00000 0.05 0.37
Q7 1 0.0239 0.8988 0.6198 11.00000 0.05 0.36
Q8 1 0.2008 -0.0069 0.6602 11.00000 0.05 0.36
Q9 1 -0.1591 0.4985 0.7532 11.00000 0.05 0.35
Q10 1 0.4299 0.0343 0.7354 11.00000 0.05 0.33
Q11 1 0.6781 0.0321 0.7337 11.00000 0.05 0.33
Q12 1 0.4321 0.1962 0.7309 11.00000 0.05 0.33
Q13 1 0.5139 0.5796 0.5138 11.00000 0.05 0.32
Q14 1 0.8530 0.0253 0.6609 11.00000 0.05 0.32
Q15 1 0.2329 0.4675 0.4175 11.00000 0.05 0.32
Q16 1 0.5939 0.5031 0.6384 11.00000 0.05 0.32
Q17 1 -0.0020 0.7570 0.7495 11.00000 0.05 0.31
Q18 1 -0.4116 0.7833 0.6789 11.00000 0.05 0.31
Q19 1 -0.2753 0.5356 0.5115 11.00000 0.05 0.31
Q20 1 0.7224 0.3255 0.6189 11.00000 0.05 0.31
REM The information below was added by Olex2.
REM
REM R1 = 0.0513 for 2289 Fo > 4sig(Fo) and 0.0980 for all 7750 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.40, deepest hole -0.63
REM Mean Shift 0, Max Shift 0.000.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0980
REM R1_gt = 0.0513
REM wR_ref = 0.1169
REM GOOF = 0.997
REM Shift_max = 0.000
REM Shift_mean = 0
REM Reflections_all = 7750
REM Reflections_gt = 2289
REM Parameters = n/a
REM Hole = -0.63
REM Peak = 0.40
REM Flack = 0.194(12)
;
_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_zz_CCDC1
_audit_block_doi 10.5517/ccdc.csd.cc248w3f
_database_code_depnum_ccdc_archive 'CCDC 1974734'
_audit_update_record
;
2019-12-30 deposited with the CCDC. 2020-02-11 downloaded from the CCDC.
;
_audit_creation_date 2019-12-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2018/3
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C18 H18 Br N O2'
_chemical_formula_sum 'C18 H18 Br N O2'
_chemical_formula_weight 360.24
_chemical_absolute_configuration .
_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'
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'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system orthorhombic
_space_group_IT_number 29
_space_group_name_H-M_alt 'P c a 21'
_space_group_name_Hall 'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
_cell_length_a 11.5591(3)
_cell_length_b 7.9650(2)
_cell_length_c 17.2106(5)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 1584.55(7)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 7062
_cell_measurement_temperature 170
_cell_measurement_theta_max 26.367
_cell_measurement_theta_min 2.557
_shelx_estimated_absorpt_T_max 0.819
_shelx_estimated_absorpt_T_min 0.638
_exptl_absorpt_coefficient_mu 2.601
_exptl_absorpt_correction_T_max 0.7454
_exptl_absorpt_correction_T_min 0.5488
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0955 before and 0.0747 after correction. The Ratio of minimum to maximum transmission is 0.7362. The \l/2 correction factor is Not present.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.510
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 736
_exptl_crystal_size_max 0.19
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_min 0.08
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0439
_diffrn_reflns_av_unetI/netI 0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.997
_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 9
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_limit_l_min -21
_diffrn_reflns_number 17118
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.385
_diffrn_reflns_theta_min 2.367
_diffrn_ambient_temperature 170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type 'D8 VENTURE '
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.801
_reflns_Friedel_fraction_full 0.874
_reflns_Friedel_fraction_max 0.858
_reflns_number_gt 2726
_reflns_number_total 3027
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT V8.38A (?, 2016)'
_computing_data_collection ?
_computing_data_reduction 'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.667
_refine_diff_density_min -0.516
_refine_diff_density_rms 0.060
_refine_ls_abs_structure_details
;
Flack x determined using 1070 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack 0.004(6)
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.047
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 201
_refine_ls_number_reflns 3027
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0382
_refine_ls_R_factor_gt 0.0314
_refine_ls_restrained_S_all 1.047
_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^)+(0.0250P)^2^+1.0224P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0688
_refine_ls_wR_factor_ref 0.0722
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups, All N(H) groups
At 1.5 times of:
All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
C13(H13A,H13B), C16(H16A,H16B), C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
N1(H1A), C8(H8), C9(H9), C2(H2), C6(H6), C5(H5)
2.c Idealised Me refined as rotating group:
C17(H17A,H17B,H17C)
2.d Idealised tetrahedral OH refined as rotating group:
O1(H1)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.84585(4) 0.05963(6) 0.22384(4) 0.03517(15) Uani 1 1 d . . . . .
O1 O 0.8247(2) 0.2675(4) 0.51115(19) 0.0252(7) Uani 1 1 d . . . . .
H1 H 0.895909 0.271128 0.501522 0.038 Uiso 1 1 calc GR . . . .
O2 O 0.5442(3) 0.7098(4) 0.4744(2) 0.0348(8) Uani 1 1 d . . . . .
N1 N 0.6654(3) 0.5148(4) 0.5258(2) 0.0206(7) Uani 1 1 d . . . . .
H1A H 0.738516 0.493305 0.536097 0.025 Uiso 1 1 calc R . . . .
C1 C 0.7644(4) 0.1061(5) 0.3174(3) 0.0245(10) Uani 1 1 d . . . . .
C18 C 0.6428(3) 0.6532(5) 0.4838(3) 0.0219(9) Uani 1 1 d . . . . .
C10 C 0.4279(4) 0.3304(6) 0.6446(3) 0.0262(10) Uani 1 1 d . . . . .
C12 C 0.5816(3) 0.3994(5) 0.5554(3) 0.0196(9) Uani 1 1 d . . . . .
C8 C 0.4948(4) 0.1270(6) 0.5513(3) 0.0231(9) Uani 1 1 d . . . . .
H8 H 0.489719 0.017313 0.529820 0.028 Uiso 1 1 calc R . . . .
C3 C 0.7671(3) 0.2090(5) 0.4478(2) 0.0201(9) Uani 1 1 d . . . . .
C9 C 0.4213(4) 0.1722(6) 0.6112(3) 0.0263(10) Uani 1 1 d . . . . .
H9 H 0.365648 0.094018 0.629658 0.032 Uiso 1 1 calc R . . . .
C2 C 0.8253(4) 0.1693(5) 0.3796(3) 0.0228(9) Uani 1 1 d . . . . .
H2 H 0.906570 0.185640 0.375910 0.027 Uiso 1 1 calc R . . . .
C6 C 0.6458(4) 0.0783(5) 0.3210(3) 0.0257(10) Uani 1 1 d . . . . .
H6 H 0.605161 0.030759 0.278332 0.031 Uiso 1 1 calc R . . . .
C11 C 0.5104(4) 0.4455(5) 0.6171(3) 0.0225(9) Uani 1 1 d . . . . .
C13 C 0.5233(4) 0.6091(6) 0.6606(3) 0.0297(11) Uani 1 1 d . . . . .
H13A H 0.459678 0.686454 0.646358 0.036 Uiso 1 1 calc R . . . .
H13B H 0.597606 0.663103 0.646795 0.036 Uiso 1 1 calc R . . . .
C7 C 0.5759(3) 0.2394(5) 0.5218(3) 0.0197(8) Uani 1 1 d . . . . .
C5 C 0.5893(4) 0.1221(5) 0.3885(3) 0.0230(9) Uani 1 1 d . . . . .
H5 H 0.508093 0.105249 0.391456 0.028 Uiso 1 1 calc R . . . .
C17 C 0.7456(4) 0.7350(6) 0.4467(3) 0.0310(11) Uani 1 1 d . . . . .
H17A H 0.738996 0.726750 0.390088 0.046 Uiso 1 1 calc GR . . . .
H17B H 0.816326 0.678215 0.463873 0.046 Uiso 1 1 calc GR . . . .
H17C H 0.748612 0.853416 0.461978 0.046 Uiso 1 1 calc GR . . . .
C4 C 0.6460(3) 0.1901(5) 0.4528(3) 0.0203(9) Uani 1 1 d . . . . .
C16 C 0.5198(5) 0.5732(7) 0.7473(3) 0.0422(15) Uani 1 1 d . . . . .
H16A H 0.588649 0.506186 0.761710 0.051 Uiso 1 1 calc R . . . .
H16B H 0.523681 0.680799 0.776013 0.051 Uiso 1 1 calc R . . . .
C14 C 0.3535(4) 0.3837(8) 0.7115(4) 0.0453(15) Uani 1 1 d . . . . .
H14A H 0.288991 0.452301 0.691001 0.054 Uiso 1 1 calc R . . . .
H14B H 0.319463 0.281931 0.735337 0.054 Uiso 1 1 calc R . . . .
C15 C 0.4118(7) 0.4791(11) 0.7720(5) 0.088(3) Uani 1 1 d . . . . .
H15A H 0.432964 0.401009 0.814441 0.105 Uiso 1 1 calc R . . . .
H15B H 0.356135 0.561271 0.793642 0.105 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
Br1 0.0283(2) 0.0474(3) 0.0297(2) -0.0098(3) 0.0076(3) -0.0065(2)
O1 0.0144(15) 0.0337(17) 0.0277(18) -0.0027(14) -0.0040(13) 0.0029(14)
O2 0.0189(17) 0.0365(18) 0.049(2) 0.0155(17) -0.0023(15) 0.0038(14)
N1 0.0123(17) 0.0219(16) 0.0276(19) 0.0020(16) -0.0023(15) 0.0000(13)
C1 0.025(2) 0.023(2) 0.025(3) -0.0017(18) 0.0050(19) -0.0001(18)
C18 0.019(2) 0.021(2) 0.025(2) 0.0045(18) -0.0009(18) -0.0010(17)
C10 0.024(2) 0.031(2) 0.024(2) 0.0007(18) 0.0017(19) -0.0050(19)
C12 0.014(2) 0.022(2) 0.023(2) 0.0039(17) -0.0018(16) -0.0006(16)
C8 0.024(2) 0.023(2) 0.023(2) 0.0016(18) -0.0022(18) -0.0046(18)
C3 0.016(2) 0.0178(19) 0.027(2) 0.0011(16) -0.0011(18) -0.0002(16)
C9 0.024(2) 0.033(2) 0.022(2) 0.0039(19) -0.0017(19) -0.0095(19)
C2 0.016(2) 0.022(2) 0.031(2) -0.0001(18) 0.0010(17) -0.0016(17)
C6 0.024(2) 0.027(2) 0.026(2) -0.0021(18) -0.0028(19) -0.0022(19)
C11 0.019(2) 0.025(2) 0.024(2) 0.0033(19) 0.0012(17) -0.0012(18)
C13 0.031(3) 0.025(2) 0.032(3) -0.003(2) -0.002(2) 0.0002(19)
C7 0.0145(19) 0.024(2) 0.021(2) 0.0029(17) -0.0032(17) 0.0003(16)
C5 0.017(2) 0.024(2) 0.028(2) 0.0022(18) 0.0004(18) -0.0023(17)
C17 0.025(2) 0.032(2) 0.036(3) 0.011(2) -0.001(2) -0.004(2)
C4 0.017(2) 0.018(2) 0.026(2) 0.0026(18) -0.0022(18) -0.0018(16)
C16 0.047(3) 0.050(3) 0.030(3) -0.015(2) 0.011(2) -0.014(3)
C14 0.044(3) 0.063(3) 0.029(4) -0.011(3) 0.017(3) -0.023(2)
C15 0.088(6) 0.105(6) 0.070(5) -0.049(5) 0.058(5) -0.054(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
Br1 C1 1.902(4) . ?
O1 H1 0.8400 . ?
O1 C3 1.361(5) . ?
O2 C18 1.237(5) . ?
N1 H1A 0.8800 . ?
N1 C18 1.344(6) . ?
N1 C12 1.429(5) . ?
C1 C2 1.377(6) . ?
C1 C6 1.389(6) . ?
C18 C17 1.497(6) . ?
C10 C9 1.388(6) . ?
C10 C11 1.405(6) . ?
C10 C14 1.497(7) . ?
C12 C11 1.393(6) . ?
C12 C7 1.401(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.384(6) . ?
C8 C7 1.392(6) . ?
C3 C2 1.389(6) . ?
C3 C4 1.410(6) . ?
C9 H9 0.9500 . ?
C2 H2 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.379(6) . ?
C11 C13 1.510(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C16 1.520(8) . ?
C7 C4 1.490(6) . ?
C5 H5 0.9500 . ?
C5 C4 1.395(6) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C15 1.517(8) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.455(10) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
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
C3 O1 H1 109.5 . . ?
C18 N1 H1A 117.0 . . ?
C18 N1 C12 126.0(3) . . ?
C12 N1 H1A 117.0 . . ?
C2 C1 Br1 118.4(3) . . ?
C2 C1 C6 122.0(4) . . ?
C6 C1 Br1 119.6(3) . . ?
O2 C18 N1 123.3(4) . . ?
O2 C18 C17 121.1(4) . . ?
N1 C18 C17 115.6(4) . . ?
C9 C10 C11 119.3(4) . . ?
C9 C10 C14 123.0(4) . . ?
C11 C10 C14 117.7(4) . . ?
C11 C12 N1 120.2(4) . . ?
C11 C12 C7 121.8(4) . . ?
C7 C12 N1 118.0(4) . . ?
C9 C8 H8 119.4 . . ?
C9 C8 C7 121.2(4) . . ?
C7 C8 H8 119.4 . . ?
O1 C3 C2 121.2(4) . . ?
O1 C3 C4 118.2(4) . . ?
C2 C3 C4 120.6(4) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 C10 120.8(4) . . ?
C8 C9 H9 119.6 . . ?
C1 C2 C3 119.4(4) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C1 C6 H6 121.2 . . ?
C5 C6 C1 117.6(4) . . ?
C5 C6 H6 121.2 . . ?
C10 C11 C13 117.5(4) . . ?
C12 C11 C10 119.1(4) . . ?
C12 C11 C13 123.2(4) . . ?
C11 C13 H13A 109.9 . . ?
C11 C13 H13B 109.9 . . ?
C11 C13 C16 108.8(4) . . ?
H13A C13 H13B 108.3 . . ?
C16 C13 H13A 109.9 . . ?
C16 C13 H13B 109.9 . . ?
C12 C7 C4 122.9(4) . . ?
C8 C7 C12 117.8(4) . . ?
C8 C7 C4 119.1(4) . . ?
C6 C5 H5 118.5 . . ?
C6 C5 C4 123.0(4) . . ?
C4 C5 H5 118.5 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C3 C4 C7 124.1(4) . . ?
C5 C4 C3 117.3(4) . . ?
C5 C4 C7 118.7(4) . . ?
C13 C16 H16A 109.0 . . ?
C13 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C15 C16 C13 113.0(6) . . ?
C15 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
C10 C14 H14A 108.4 . . ?
C10 C14 H14B 108.4 . . ?
H14A C14 H14B 107.4 . . ?
C15 C14 C10 115.6(5) . . ?
C15 C14 H14A 108.4 . . ?
C15 C14 H14B 108.4 . . ?
C16 C15 H15A 108.3 . . ?
C16 C15 H15B 108.3 . . ?
C14 C15 C16 116.0(6) . . ?
C14 C15 H15A 108.3 . . ?
C14 C15 H15B 108.3 . . ?
H15A C15 H15B 107.4 . . ?
_iucr_refine_instructions_details
;
TITL zz_b.res in Pca2(1)
zz.res
created by SHELXL-2018/3 at 14:04:49 on 30-Dec-2019
REM Old TITL zz in Pca2(1)
REM SHELXT solution in Pca2(1)
REM R1 0.100, Rweak 0.010, Alpha 0.009, Orientation as input
REM Flack x = 0.017 ( 0.006 ) from Parsons' quotients
REM Formula found by SHELXT: C18 N O2 Br
CELL 0.71073 11.5591 7.965 17.2106 90 90 90
ZERR 4 0.0003 0.0002 0.0005 0 0 0
LATT -1
SYMM -X,-Y,0.5+Z
SYMM 0.5+X,-Y,+Z
SYMM 0.5-X,+Y,0.5+Z
SFAC C H Br N O
UNIT 72 72 4 4 8
L.S. 10
PLAN 20
SIZE 0.19 0.12 0.08
TEMP -103.15
BOND $H
LIST 6
fmap 2
ACTA
REM
REM
REM
WGHT 0.025000 1.022400
FVAR 0.76078
BR1 3 0.845851 0.059625 0.223838 11.00000 0.02834 0.04743 =
0.02975 -0.00981 0.00763 -0.00655
O1 5 0.824711 0.267519 0.511152 11.00000 0.01436 0.03367 =
0.02767 -0.00267 -0.00398 0.00293
AFIX 147
H1 2 0.895909 0.271128 0.501522 11.00000 -1.50000
AFIX 0
O2 5 0.544208 0.709824 0.474376 11.00000 0.01885 0.03651 =
0.04911 0.01546 -0.00227 0.00378
N1 4 0.665422 0.514808 0.525832 11.00000 0.01225 0.02191 =
0.02755 0.00198 -0.00227 0.00000
AFIX 43
H1A 2 0.738516 0.493305 0.536097 11.00000 -1.20000
AFIX 0
C1 1 0.764360 0.106139 0.317420 11.00000 0.02537 0.02290 =
0.02509 -0.00174 0.00498 -0.00010
C18 1 0.642841 0.653212 0.483776 11.00000 0.01936 0.02092 =
0.02537 0.00449 -0.00087 -0.00103
C10 1 0.427904 0.330441 0.644640 11.00000 0.02375 0.03076 =
0.02410 0.00069 0.00168 -0.00498
C12 1 0.581640 0.399417 0.555394 11.00000 0.01354 0.02174 =
0.02348 0.00393 -0.00176 -0.00059
C8 1 0.494762 0.126981 0.551255 11.00000 0.02362 0.02319 =
0.02253 0.00160 -0.00222 -0.00456
AFIX 43
H8 2 0.489719 0.017313 0.529820 11.00000 -1.20000
AFIX 0
C3 1 0.767056 0.208969 0.447759 11.00000 0.01574 0.01777 =
0.02691 0.00107 -0.00105 -0.00015
C9 1 0.421281 0.172219 0.611194 11.00000 0.02409 0.03320 =
0.02162 0.00395 -0.00173 -0.00952
AFIX 43
H9 2 0.365648 0.094018 0.629658 11.00000 -1.20000
AFIX 0
C2 1 0.825343 0.169308 0.379587 11.00000 0.01602 0.02169 =
0.03078 -0.00013 0.00097 -0.00159
AFIX 43
H2 2 0.906570 0.185640 0.375910 11.00000 -1.20000
AFIX 0
C6 1 0.645835 0.078294 0.320954 11.00000 0.02405 0.02712 =
0.02589 -0.00209 -0.00281 -0.00221
AFIX 43
H6 2 0.605161 0.030759 0.278332 11.00000 -1.20000
AFIX 0
C11 1 0.510418 0.445504 0.617101 11.00000 0.01860 0.02497 =
0.02386 0.00331 0.00115 -0.00115
C13 1 0.523264 0.609104 0.660627 11.00000 0.03134 0.02541 =
0.03221 -0.00261 -0.00207 0.00021
AFIX 23
H13A 2 0.459678 0.686454 0.646358 11.00000 -1.20000
H13B 2 0.597606 0.663103 0.646795 11.00000 -1.20000
AFIX 0
C7 1 0.575946 0.239363 0.521814 11.00000 0.01446 0.02377 =
0.02093 0.00293 -0.00324 0.00030
C5 1 0.589337 0.122118 0.388540 11.00000 0.01667 0.02389 =
0.02842 0.00220 0.00039 -0.00231
AFIX 43
H5 2 0.508093 0.105249 0.391456 11.00000 -1.20000
AFIX 0
C17 1 0.745559 0.734953 0.446732 11.00000 0.02519 0.03160 =
0.03613 0.01052 -0.00055 -0.00387
AFIX 137
H17A 2 0.738996 0.726750 0.390088 11.00000 -1.50000
H17B 2 0.816326 0.678215 0.463873 11.00000 -1.50000
H17C 2 0.748612 0.853416 0.461978 11.00000 -1.50000
AFIX 0
C4 1 0.645970 0.190073 0.452822 11.00000 0.01683 0.01835 =
0.02564 0.00258 -0.00222 -0.00176
C16 1 0.519770 0.573207 0.747331 11.00000 0.04668 0.05000 =
0.02985 -0.01469 0.01135 -0.01437
AFIX 23
H16A 2 0.588649 0.506186 0.761710 11.00000 -1.20000
H16B 2 0.523681 0.680799 0.776013 11.00000 -1.20000
AFIX 0
C14 1 0.353544 0.383660 0.711496 11.00000 0.04363 0.06337 =
0.02897 -0.01142 0.01709 -0.02286
AFIX 23
H14A 2 0.288991 0.452301 0.691001 11.00000 -1.20000
H14B 2 0.319463 0.281931 0.735337 11.00000 -1.20000
AFIX 0
C15 1 0.411789 0.479147 0.772027 11.00000 0.08787 0.10492 =
0.07012 -0.04905 0.05781 -0.05445
AFIX 23
H15A 2 0.432964 0.401009 0.814441 11.00000 -1.20000
H15B 2 0.356135 0.561271 0.793642 11.00000 -1.20000
AFIX 0
HKLF 4
REM zz_b.res in Pca2(1)
REM wR2 = 0.0722, GooF = S = 1.047, Restrained GooF = 1.047 for all data
REM R1 = 0.0314 for 2726 Fo > 4sig(Fo) and 0.0382 for all 3027 data
REM 201 parameters refined using 1 restraints
END
WGHT 0.0236 1.0671
REM Highest difference peak 0.667, deepest hole -0.516, 1-sigma level 0.060
Q1 1 0.3619 0.5383 0.7299 11.00000 0.05 0.67
Q2 1 0.2886 0.3227 0.7228 11.00000 0.05 0.39
Q3 1 0.7978 0.1272 0.2118 11.00000 0.05 0.34
Q4 1 0.4119 0.3306 0.7210 11.00000 0.05 0.30
Q5 1 0.3088 0.5925 0.7147 11.00000 0.05 0.28
Q6 1 0.3554 0.5372 0.8144 11.00000 0.05 0.24
Q7 1 0.4178 0.4367 0.6723 11.00000 0.05 0.23
Q8 1 0.7170 0.8155 0.4293 11.00000 0.05 0.22
Q9 1 0.5652 0.3177 0.5269 11.00000 0.05 0.21
Q10 1 0.8750 0.2130 0.2477 11.00000 0.05 0.20
Q11 1 0.5182 0.2080 0.5324 11.00000 0.05 0.19
Q12 1 0.9798 0.1413 0.2814 11.00000 0.05 0.19
Q13 1 0.7471 0.4528 0.5132 11.00000 0.05 0.19
Q14 1 0.4503 0.6652 0.4225 11.00000 0.05 0.19
Q15 1 0.6156 0.1965 0.4177 11.00000 0.05 0.19
Q16 1 0.2759 0.5392 0.6908 11.00000 0.05 0.19
Q17 1 0.7814 -0.0738 0.2184 11.00000 0.05 0.18
Q18 1 0.4075 0.2743 0.6210 11.00000 0.05 0.18
Q19 1 0.7979 0.1203 0.3488 11.00000 0.05 0.18
Q20 1 0.5367 -0.0374 0.2273 11.00000 0.05 0.18
REM The information below was added by Olex2.
REM
REM R1 = 0.0314 for 2726 Fo > 4sig(Fo) and 0.0382 for all 18352 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.67, deepest hole -0.52
REM Mean Shift 0, Max Shift -0.001.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0382
REM R1_gt = 0.0314
REM wR_ref = 0.0722
REM GOOF = 1.047
REM Shift_max = -0.001
REM Shift_mean = 0
REM Reflections_all = 18352
REM Reflections_gt = 2726
REM Parameters = n/a
REM Hole = -0.52
REM Peak = 0.67
REM Flack = 0.004(6)
;
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_220191300_0m
_audit_block_doi 10.5517/ccdc.csd.cc248w4g
_database_code_depnum_ccdc_archive 'CCDC 1974735'
_audit_update_record
;
2019-12-30 deposited with the CCDC. 2020-02-11 downloaded from the CCDC.
;
_audit_creation_date 2019-12-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2018/3
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C18 H14 Br N O2'
_chemical_formula_sum 'C18 H14 Br N O2'
_chemical_formula_weight 356.21
_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'
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'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system orthorhombic
_space_group_IT_number 61
_space_group_name_H-M_alt 'P b c a'
_space_group_name_Hall '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
_cell_length_a 8.3242(3)
_cell_length_b 12.6129(3)
_cell_length_c 28.2407(8)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 2965.06(15)
_cell_formula_units_Z 8
_cell_measurement_reflns_used 6203
_cell_measurement_temperature 170
_cell_measurement_theta_max 26.055
_cell_measurement_theta_min 2.841
_shelx_estimated_absorpt_T_max 0.808
_shelx_estimated_absorpt_T_min 0.665
_exptl_absorpt_coefficient_mu 2.779
_exptl_absorpt_correction_T_max 0.7454
_exptl_absorpt_correction_T_min 0.5989
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0912 before and 0.0599 after correction. The Ratio of minimum to maximum transmission is 0.8035. The \l/2 correction factor is Not present.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.596
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 1440
_exptl_crystal_size_max 0.16
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_min 0.08
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0860
_diffrn_reflns_av_unetI/netI 0.0397
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 35
_diffrn_reflns_limit_l_min -35
_diffrn_reflns_number 32027
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.370
_diffrn_reflns_theta_min 2.841
_diffrn_ambient_temperature 170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type 'D8 VENTURE'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2230
_reflns_number_total 3030
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT V8.38A (?, 2016)'
_computing_data_collection ?
_computing_data_reduction 'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.383
_refine_diff_density_min -0.333
_refine_diff_density_rms 0.075
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.014
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 201
_refine_ls_number_reflns 3030
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0632
_refine_ls_R_factor_gt 0.0354
_refine_ls_restrained_S_all 1.014
_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^)+(0.0274P)^2^+4.1331P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0689
_refine_ls_wR_factor_ref 0.0810
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All N(H) groups
At 1.5 times of:
All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
N1(H1A), C16(H16), C13(H13), C15(H15), C9(H9), C10(H10), C5(H5), C2(H2),
C4(H4), C3(H3)
2.b Idealised Me refined as rotating group:
C18(H18A,H18B,H18C)
2.c Idealised tetrahedral OH refined as rotating group:
O1(H1)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.31984(4) 0.89019(2) 0.21217(2) 0.03085(11) Uani 1 1 d . . . . .
O1 O 0.5266(3) 0.79763(15) 0.38150(7) 0.0248(5) Uani 1 1 d . . . . .
H1 H 0.545500 0.862820 0.379090 0.037 Uiso 1 1 calc GR . . . .
O2 O 0.9285(3) 0.50916(15) 0.36668(8) 0.0282(5) Uani 1 1 d . . . . .
N1 N 0.7446(3) 0.63309(18) 0.38759(8) 0.0208(5) Uani 1 1 d . . . . .
H1A H 0.727571 0.701427 0.391363 0.025 Uiso 1 1 calc R . . . .
C7 C 0.6143(3) 0.5629(2) 0.39750(10) 0.0201(6) Uani 1 1 d . . . . .
C16 C 0.3748(3) 0.6161(2) 0.29155(10) 0.0228(6) Uani 1 1 d . . . . .
H16 H 0.356089 0.542389 0.287414 0.027 Uiso 1 1 calc R . . . .
C14 C 0.3625(3) 0.7917(2) 0.26175(11) 0.0239(7) Uani 1 1 d . . . . .
C12 C 0.4646(3) 0.7605(2) 0.33941(10) 0.0215(6) Uani 1 1 d . . . . .
C17 C 0.8914(4) 0.6029(2) 0.37295(10) 0.0209(6) Uani 1 1 d . . . . .
C11 C 0.4421(3) 0.6509(2) 0.33418(10) 0.0198(6) Uani 1 1 d . . . . .
C6 C 0.6321(3) 0.4870(2) 0.43442(10) 0.0218(6) Uani 1 1 d . . . . .
C8 C 0.4729(3) 0.5725(2) 0.37264(10) 0.0207(6) Uani 1 1 d . . . . .
C13 C 0.4254(3) 0.8305(2) 0.30329(10) 0.0226(7) Uani 1 1 d . . . . .
H13 H 0.441896 0.904498 0.307244 0.027 Uiso 1 1 calc R . . . .
C15 C 0.3343(4) 0.6844(2) 0.25520(11) 0.0254(7) Uani 1 1 d . . . . .
H15 H 0.288656 0.658569 0.226606 0.030 Uiso 1 1 calc R . . . .
C9 C 0.3454(4) 0.5007(2) 0.38334(11) 0.0244(7) Uani 1 1 d . . . . .
H9 H 0.248043 0.505155 0.365915 0.029 Uiso 1 1 calc R . . . .
C1 C 0.5022(4) 0.4176(2) 0.44487(11) 0.0237(7) Uani 1 1 d . . . . .
C10 C 0.3598(4) 0.4263(2) 0.41778(11) 0.0258(7) Uani 1 1 d . . . . .
H10 H 0.272930 0.379378 0.423796 0.031 Uiso 1 1 calc R . . . .
C18 C 1.0113(4) 0.6901(2) 0.36545(11) 0.0284(7) Uani 1 1 d . . . . .
H18A H 1.097004 0.684241 0.389105 0.043 Uiso 1 1 calc GR . . . .
H18B H 0.957825 0.758894 0.368696 0.043 Uiso 1 1 calc GR . . . .
H18C H 1.057510 0.683983 0.333646 0.043 Uiso 1 1 calc GR . . . .
C5 C 0.7723(4) 0.4800(2) 0.46318(11) 0.0279(7) Uani 1 1 d . . . . .
H5 H 0.860342 0.526073 0.457344 0.034 Uiso 1 1 calc R . . . .
C2 C 0.5166(4) 0.3442(2) 0.48225(12) 0.0295(7) Uani 1 1 d . . . . .
H2 H 0.429888 0.297630 0.488959 0.035 Uiso 1 1 calc R . . . .
C4 C 0.7813(4) 0.4075(3) 0.49911(12) 0.0325(8) Uani 1 1 d . . . . .
H4 H 0.876232 0.403465 0.517708 0.039 Uiso 1 1 calc R . . . .
C3 C 0.6526(4) 0.3390(2) 0.50894(12) 0.0329(8) Uani 1 1 d . . . . .
H3 H 0.660423 0.289216 0.534086 0.039 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
Br1 0.03624(19) 0.02802(17) 0.02831(18) 0.00464(14) -0.00588(15) 0.00076(15)
O1 0.0313(12) 0.0171(10) 0.0262(12) -0.0032(8) -0.0065(9) 0.0012(10)
O2 0.0296(12) 0.0172(10) 0.0378(13) -0.0043(9) 0.0048(10) 0.0029(9)
N1 0.0183(12) 0.0159(12) 0.0281(13) -0.0014(10) 0.0003(12) -0.0005(10)
C7 0.0181(15) 0.0165(13) 0.0257(16) -0.0028(12) 0.0027(12) -0.0004(12)
C16 0.0222(15) 0.0181(13) 0.0280(16) -0.0028(13) 0.0020(13) -0.0040(12)
C14 0.0182(15) 0.0272(15) 0.0264(17) 0.0040(13) 0.0001(13) 0.0018(13)
C12 0.0183(15) 0.0222(14) 0.0240(16) -0.0037(12) -0.0005(12) 0.0024(12)
C17 0.0199(15) 0.0229(15) 0.0199(15) 0.0006(12) -0.0010(12) -0.0014(13)
C11 0.0150(15) 0.0198(14) 0.0246(16) -0.0010(12) 0.0009(12) 0.0009(12)
C6 0.0193(15) 0.0213(14) 0.0247(16) -0.0027(12) 0.0005(13) 0.0030(12)
C8 0.0196(15) 0.0168(13) 0.0257(16) -0.0035(12) 0.0012(13) 0.0018(12)
C13 0.0227(16) 0.0189(15) 0.0263(16) -0.0022(12) 0.0003(13) -0.0008(13)
C15 0.0240(17) 0.0265(15) 0.0256(16) -0.0067(13) -0.0037(13) -0.0018(13)
C9 0.0195(16) 0.0238(15) 0.0300(17) -0.0024(13) -0.0044(13) -0.0009(13)
C1 0.0247(17) 0.0189(14) 0.0275(17) -0.0018(12) 0.0008(13) 0.0035(12)
C10 0.0205(16) 0.0190(14) 0.0380(19) -0.0007(13) 0.0005(14) -0.0039(12)
C18 0.0263(17) 0.0243(16) 0.0347(19) -0.0013(13) 0.0029(14) -0.0021(14)
C5 0.0249(17) 0.0275(16) 0.0314(18) -0.0005(14) 0.0001(14) -0.0008(14)
C2 0.0284(18) 0.0216(15) 0.039(2) 0.0022(14) 0.0005(15) 0.0012(14)
C4 0.030(2) 0.0353(18) 0.0320(19) 0.0033(14) -0.0036(14) 0.0063(15)
C3 0.037(2) 0.0266(16) 0.0353(19) 0.0089(14) 0.0033(16) 0.0067(15)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C14 1.905(3) . ?
O1 H1 0.8400 . ?
O1 C12 1.378(3) . ?
O2 C17 1.235(3) . ?
N1 H1A 0.8800 . ?
N1 C7 1.428(4) . ?
N1 C17 1.344(4) . ?
C7 C6 1.423(4) . ?
C7 C8 1.376(4) . ?
C16 H16 0.9500 . ?
C16 C11 1.399(4) . ?
C16 C15 1.381(4) . ?
C14 C13 1.375(4) . ?
C14 C15 1.386(4) . ?
C12 C11 1.402(4) . ?
C12 C13 1.388(4) . ?
C17 C18 1.500(4) . ?
C11 C8 1.492(4) . ?
C6 C1 1.422(4) . ?
C6 C5 1.424(4) . ?
C8 C9 1.427(4) . ?
C13 H13 0.9500 . ?
C15 H15 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.357(4) . ?
C1 C10 1.415(4) . ?
C1 C2 1.409(4) . ?
C10 H10 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C5 H5 0.9500 . ?
C5 C4 1.368(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.362(5) . ?
C4 H4 0.9500 . ?
C4 C3 1.404(5) . ?
C3 H3 0.9500 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O1 H1 109.5 . . ?
C7 N1 H1A 117.4 . . ?
C17 N1 H1A 117.4 . . ?
C17 N1 C7 125.1(2) . . ?
C6 C7 N1 118.8(3) . . ?
C8 C7 N1 119.7(3) . . ?
C8 C7 C6 121.5(3) . . ?
C11 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
C15 C16 C11 122.8(3) . . ?
C13 C14 Br1 117.8(2) . . ?
C13 C14 C15 121.7(3) . . ?
C15 C14 Br1 120.5(2) . . ?
O1 C12 C11 118.4(3) . . ?
O1 C12 C13 120.3(2) . . ?
C13 C12 C11 121.2(3) . . ?
O2 C17 N1 122.8(3) . . ?
O2 C17 C18 121.0(3) . . ?
N1 C17 C18 116.2(2) . . ?
C16 C11 C12 117.0(3) . . ?
C16 C11 C8 119.2(2) . . ?
C12 C11 C8 123.7(3) . . ?
C7 C6 C5 123.0(3) . . ?
C1 C6 C7 119.1(3) . . ?
C1 C6 C5 117.8(3) . . ?
C7 C8 C11 125.3(3) . . ?
C7 C8 C9 118.2(3) . . ?
C9 C8 C11 116.6(3) . . ?
C14 C13 C12 119.3(3) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C16 C15 C14 117.9(3) . . ?
C16 C15 H15 121.0 . . ?
C14 C15 H15 121.0 . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.7(3) . . ?
C10 C9 H9 119.2 . . ?
C10 C1 C6 118.5(3) . . ?
C2 C1 C6 119.7(3) . . ?
C2 C1 C10 121.8(3) . . ?
C9 C10 C1 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
C1 C10 H10 119.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.2(3) . . ?
C3 C2 H2 119.4 . . ?
C5 C4 H4 119.5 . . ?
C5 C4 C3 121.1(3) . . ?
C3 C4 H4 119.5 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
_iucr_refine_instructions_details
;
TITL 220191300_0m_a.res in Pbca
220191300_0m.res
created by SHELXL-2018/3 at 14:33:02 on 30-Dec-2019
REM Old TITL 220191300_0m in Pbca
REM SHELXT solution in Pbca
REM R1 0.110, Rweak 0.004, Alpha 0.040, Orientation as input
REM Formula found by SHELXT: C18 N O2 Br
CELL 0.71073 8.3242 12.6129 28.2407 90 90 90
ZERR 8 0.0003 0.0003 0.0008 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H Br N O
UNIT 144 112 8 8 16
L.S. 4
PLAN 20
SIZE 0.16 0.12 0.08
TEMP -103.15
BOND $H
list 4
fmap 2
ACTA
REM
REM
REM
WGHT 0.027400 4.133100
FVAR 0.28466
BR1 3 0.319838 0.890186 0.212167 11.00000 0.03624 0.02802 =
0.02831 0.00464 -0.00588 0.00076
O1 5 0.526551 0.797630 0.381503 11.00000 0.03127 0.01708 =
0.02617 -0.00322 -0.00650 0.00119
AFIX 147
H1 2 0.545500 0.862820 0.379090 11.00000 -1.50000
AFIX 0
O2 5 0.928530 0.509155 0.366683 11.00000 0.02957 0.01719 =
0.03776 -0.00434 0.00483 0.00291
N1 4 0.744640 0.633092 0.387591 11.00000 0.01835 0.01589 =
0.02808 -0.00142 0.00029 -0.00047
AFIX 43
H1A 2 0.727571 0.701427 0.391363 11.00000 -1.20000
AFIX 0
C7 1 0.614316 0.562886 0.397499 11.00000 0.01806 0.01648 =
0.02568 -0.00281 0.00270 -0.00040
C16 1 0.374791 0.616112 0.291546 11.00000 0.02219 0.01812 =
0.02800 -0.00284 0.00196 -0.00404
AFIX 43
H16 2 0.356089 0.542389 0.287414 11.00000 -1.20000
AFIX 0
C14 1 0.362507 0.791675 0.261751 11.00000 0.01825 0.02722 =
0.02635 0.00396 0.00014 0.00180
C12 1 0.464624 0.760456 0.339407 11.00000 0.01829 0.02218 =
0.02399 -0.00368 -0.00051 0.00238
C17 1 0.891373 0.602943 0.372952 11.00000 0.01993 0.02290 =
0.01992 0.00060 -0.00103 -0.00139
C11 1 0.442121 0.650942 0.334181 11.00000 0.01504 0.01985 =
0.02457 -0.00104 0.00092 0.00089
C6 1 0.632134 0.487004 0.434420 11.00000 0.01931 0.02131 =
0.02474 -0.00266 0.00052 0.00302
C8 1 0.472950 0.572486 0.372638 11.00000 0.01957 0.01677 =
0.02566 -0.00352 0.00122 0.00175
C13 1 0.425421 0.830494 0.303294 11.00000 0.02272 0.01888 =
0.02627 -0.00223 0.00028 -0.00085
AFIX 43
H13 2 0.441896 0.904498 0.307244 11.00000 -1.20000
AFIX 0
C15 1 0.334343 0.684369 0.255198 11.00000 0.02405 0.02652 =
0.02558 -0.00671 -0.00370 -0.00175
AFIX 43
H15 2 0.288656 0.658569 0.226606 11.00000 -1.20000
AFIX 0
C9 1 0.345425 0.500715 0.383344 11.00000 0.01955 0.02376 =
0.03004 -0.00244 -0.00445 -0.00088
AFIX 43
H9 2 0.248043 0.505155 0.365915 11.00000 -1.20000
AFIX 0
C1 1 0.502201 0.417602 0.444874 11.00000 0.02467 0.01887 =
0.02755 -0.00176 0.00079 0.00349
C10 1 0.359796 0.426333 0.417778 11.00000 0.02054 0.01898 =
0.03797 -0.00073 0.00055 -0.00393
AFIX 43
H10 2 0.272930 0.379378 0.423796 11.00000 -1.20000
AFIX 0
C18 1 1.011320 0.690063 0.365450 11.00000 0.02625 0.02432 =
0.03465 -0.00128 0.00291 -0.00206
AFIX 137
H18A 2 1.097004 0.684241 0.389105 11.00000 -1.50000
H18B 2 0.957825 0.758894 0.368696 11.00000 -1.50000
H18C 2 1.057510 0.683983 0.333646 11.00000 -1.50000
AFIX 0
C5 1 0.772283 0.479975 0.463176 11.00000 0.02494 0.02748 =
0.03136 -0.00055 0.00007 -0.00077
AFIX 43
H5 2 0.860342 0.526073 0.457344 11.00000 -1.20000
AFIX 0
C2 1 0.516594 0.344246 0.482252 11.00000 0.02844 0.02157 =
0.03861 0.00218 0.00048 0.00118
AFIX 43
H2 2 0.429888 0.297630 0.488959 11.00000 -1.20000
AFIX 0
C4 1 0.781341 0.407508 0.499106 11.00000 0.03008 0.03534 =
0.03198 0.00330 -0.00363 0.00628
AFIX 43
H4 2 0.876232 0.403465 0.517708 11.00000 -1.20000
AFIX 0
C3 1 0.652640 0.338988 0.508942 11.00000 0.03675 0.02657 =
0.03527 0.00889 0.00325 0.00666
AFIX 43
H3 2 0.660423 0.289216 0.534086 11.00000 -1.20000
AFIX 0
HKLF 4
REM 220191300_0m_a.res in Pbca
REM wR2 = 0.0810, GooF = S = 1.014, Restrained GooF = 1.014 for all data
REM R1 = 0.0354 for 2230 Fo > 4sig(Fo) and 0.0632 for all 3030 data
REM 201 parameters refined using 0 restraints
END
WGHT 0.0211 3.7246
REM Highest difference peak 0.383, deepest hole -0.333, 1-sigma level 0.075
Q1 1 0.1869 0.8380 0.2111 11.00000 0.05 0.38
Q2 1 0.7021 0.4643 0.4397 11.00000 0.05 0.38
Q3 1 0.6348 0.5161 0.4123 11.00000 0.05 0.34
Q4 1 0.5385 0.9025 0.2883 11.00000 0.05 0.33
Q5 1 0.1850 0.3947 0.3616 11.00000 0.05 0.30
Q6 1 0.5808 0.4393 0.4320 11.00000 0.05 0.28
Q7 1 0.7922 0.4203 0.4695 11.00000 0.05 0.28
Q8 1 0.3455 0.6572 0.2799 11.00000 0.05 0.27
Q9 1 0.9773 0.4826 0.3893 11.00000 0.05 0.26
Q10 1 0.6725 0.5969 0.3940 11.00000 0.05 0.26
Q11 1 0.4521 0.8748 0.3096 11.00000 0.05 0.26
Q12 1 0.3187 0.7420 0.2615 11.00000 0.05 0.26
Q13 1 0.4750 0.7670 0.3607 11.00000 0.05 0.25
Q14 1 0.1397 0.4403 0.4289 11.00000 0.05 0.25
Q15 1 0.4251 0.7961 0.3268 11.00000 0.05 0.24
Q16 1 0.4258 0.8264 0.2135 11.00000 0.05 0.24
Q17 1 0.5690 0.4560 0.4417 11.00000 0.05 0.24
Q18 1 0.7463 0.6058 0.3303 11.00000 0.05 0.24
Q19 1 0.8274 0.4806 0.4517 11.00000 0.05 0.24
Q20 1 0.1097 0.3250 0.4276 11.00000 0.05 0.24
REM The information below was added by Olex2.
REM
REM R1 = 0.0354 for 2230 Fo > 4sig(Fo) and 0.0632 for all 34571 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.38, deepest hole -0.33
REM Mean Shift 0, Max Shift 0.002.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0632
REM R1_gt = 0.0354
REM wR_ref = 0.0810
REM GOOF = 1.014
REM Shift_max = 0.002
REM Shift_mean = 0
REM Reflections_all = 34571
REM Reflections_gt = 2230
REM Parameters = n/a
REM Hole = -0.33
REM Peak = 0.38
REM Flack = n/a
;
_olex2_submission_special_instructions 'No special instructions were received'