Electronic Supplementary Material for CrystEngComm This Journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 1350 _publ_requested_journal CrystEngComm loop_ _publ_author_name 'Joseph Michael' 'Andreas Lemmerer' _publ_contact_author_name 'Joseph Michae' _publ_contact_author_address ; School of Chemistry University of the Witwatersrand Johannesburg Wits 2050 SOUTH AFRICA ; _publ_contact_author_email 'JOSEPH.MICHAEL@WITS.AC.ZA ' _publ_section_title ;Hydrogen bonding patterns in a series of 1-arylcycloalkanecarboxamides ; _publ_requested_category FO # Attachment 'Lemmerer_and_Michael_carboxamides.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2007-01-15 at 15:07:12 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : 6a_jm12_a smart data_1 _database_code_depnum_ccdc_archive 'CCDC 649368' _audit_creation_date 2007-01-15T15:07:12-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 1-Phenylcyclopentanecarboxamide ; _chemical_formula_moiety 'C12 H15 N O' _chemical_formula_sum 'C12 H15 N O' _chemical_formula_weight 189.25 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.140(2) _cell_length_b 7.3843(11) _cell_length_c 10.2066(15) _cell_angle_alpha 90 _cell_angle_beta 109.291(10) _cell_angle_gamma 90 _cell_volume 1005.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1009 _cell_measurement_theta_min 3.053 _cell_measurement_theta_max 28.096 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.25 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.05 -1 0 0 0.05 -1 0 2 0.1 1 0 -2 0.1 4 3 -5 0.15 -1 -2 0 0.15 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 1999)' _exptl_absorpt_correction_T_min 0.2432 _exptl_absorpt_correction_T_max 0.5325 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 1999) ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_av_R_equivalents 0.0805 _diffrn_reflns_av_unetI/netI 0.0492 _diffrn_reflns_number 9869 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 2430 _reflns_number_gt 1963 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART-NT (Bruker, 1998)' _computing_cell_refinement 'Bruker SAINT+ (Bruker, 1999)' _computing_data_reduction 'Bruker SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997b)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0613P)^2^+0.1747P] 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_number_reflns 2430 _refine_ls_number_parameters 133 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0601 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1184 _refine_ls_wR_factor_gt 0.1102 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.002 _refine_diff_density_max 0.224 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.052 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1A C 0.32770(8) 0.61421(15) 0.39698(11) 0.0213(2) Uani 1 1 d . . . C2A C 0.31233(9) 0.51141(16) 0.52059(11) 0.0258(3) Uani 1 1 d . . . H2A1 H 0.3773 0.4867 0.5937 0.031 Uiso 1 1 calc R . . H2A2 H 0.2692 0.5813 0.5614 0.031 Uiso 1 1 calc R . . C3A C 0.26121(10) 0.33523(17) 0.45493(13) 0.0311(3) Uani 1 1 d . . . H3A1 H 0.1881 0.3534 0.411 0.037 Uiso 1 1 calc R . . H3A2 H 0.2727 0.2385 0.5256 0.037 Uiso 1 1 calc R . . C4A C 0.30998(11) 0.28569(17) 0.34519(14) 0.0321(3) Uani 1 1 d . . . H4A1 H 0.2585 0.246 0.258 0.038 Uiso 1 1 calc R . . H4A2 H 0.3592 0.1867 0.3793 0.038 Uiso 1 1 calc R . . C5A C 0.36261(9) 0.45966(16) 0.32068(12) 0.0253(3) Uani 1 1 d . . . H5A1 H 0.3433 0.4862 0.2202 0.03 Uiso 1 1 calc R . . H5A2 H 0.4363 0.4455 0.3586 0.03 Uiso 1 1 calc R . . C6A C 0.40635(8) 0.76469(15) 0.44616(11) 0.0220(2) Uani 1 1 d . . . C7A C 0.22917(9) 0.70401(16) 0.30962(12) 0.0239(3) Uani 1 1 d . . . C8A C 0.19924(10) 0.86402(19) 0.35633(15) 0.0361(3) Uani 1 1 d . . . H8A H 0.241 0.9164 0.4406 0.043 Uiso 1 1 calc R . . C9A C 0.10982(11) 0.9489(2) 0.28264(17) 0.0433(4) Uani 1 1 d . . . H9A H 0.091 1.0579 0.317 0.052 Uiso 1 1 calc R . . C10A C 0.04849(10) 0.8758(2) 0.16027(17) 0.0426(4) Uani 1 1 d . . . H10A H -0.0127 0.9336 0.1097 0.051 Uiso 1 1 calc R . . C11A C 0.07677(11) 0.7178(2) 0.11161(16) 0.0465(4) Uani 1 1 d . . . H11A H 0.0348 0.667 0.0268 0.056 Uiso 1 1 calc R . . C12A C 0.16639(10) 0.6316(2) 0.18568(14) 0.0355(3) Uani 1 1 d . . . H12A H 0.1846 0.5224 0.151 0.043 Uiso 1 1 calc R . . N1A N 0.45067(8) 0.82031(15) 0.35587(11) 0.0265(2) Uani 1 1 d . . . H1As H 0.4943(12) 0.916(2) 0.3790(15) 0.032 Uiso 1 1 d . . . H1Aa H 0.4320(11) 0.777(2) 0.2692(17) 0.032 Uiso 1 1 d . . . O1A O 0.42683(6) 0.83310(11) 0.56354(8) 0.0270(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1A 0.0249(6) 0.0213(5) 0.0186(5) -0.0006(4) 0.0084(4) 0.0001(4) C2A 0.0330(6) 0.0252(6) 0.0208(5) 0.0011(4) 0.0111(5) 0.0000(5) C3A 0.0429(7) 0.0260(6) 0.0277(6) 0.0004(5) 0.0161(6) -0.0046(5) C4A 0.0449(7) 0.0227(6) 0.0331(7) -0.0029(5) 0.0189(6) -0.0022(5) C5A 0.0306(6) 0.0236(6) 0.0243(6) -0.0015(4) 0.0124(5) 0.0014(5) C6A 0.0234(5) 0.0217(5) 0.0203(5) 0.0017(4) 0.0064(4) 0.0029(4) C7A 0.0243(6) 0.0255(6) 0.0233(6) 0.0031(4) 0.0095(4) -0.0013(4) C8A 0.0314(7) 0.0336(7) 0.0392(7) -0.0042(6) 0.0062(6) 0.0046(5) C9A 0.0349(7) 0.0351(8) 0.0588(9) 0.0035(7) 0.0141(7) 0.0084(6) C10A 0.0263(7) 0.0479(9) 0.0509(9) 0.0185(7) 0.0091(6) 0.0039(6) C11A 0.0324(7) 0.0591(10) 0.0380(8) 0.0020(7) -0.0019(6) -0.0019(7) C12A 0.0331(7) 0.0387(7) 0.0315(7) -0.0040(6) 0.0062(6) -0.0009(5) N1A 0.0303(5) 0.0287(6) 0.0221(5) -0.0022(4) 0.0106(4) -0.0057(4) O1A 0.0320(5) 0.0286(5) 0.0210(4) -0.0033(3) 0.0096(3) -0.0027(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1A C7A 1.5346(16) . ? C1A C6A 1.5345(16) . ? C1A C2A 1.5481(15) . ? C1A C5A 1.5514(16) . ? C2A C3A 1.5310(17) . ? C2A H2A1 0.99 . ? C2A H2A2 0.99 . ? C3A C4A 1.5409(17) . ? C3A H3A1 0.99 . ? C3A H3A2 0.99 . ? C4A C5A 1.5459(17) . ? C4A H4A1 0.99 . ? C4A H4A2 0.99 . ? C5A H5A1 0.99 . ? C5A H5A2 0.99 . ? C6A O1A 1.2431(14) . ? C6A N1A 1.3387(15) . ? C7A C8A 1.3913(18) . ? C7A C12A 1.3899(18) . ? C8A C9A 1.3888(19) . ? C8A H8A 0.95 . ? C9A C10A 1.374(2) . ? C9A H9A 0.95 . ? C10A C11A 1.378(2) . ? C10A H10A 0.95 . ? C11A C12A 1.396(2) . ? C11A H11A 0.95 . ? C12A H12A 0.95 . ? N1A H1As 0.914(17) . ? N1A H1Aa 0.894(16) . ? 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 C7A C1A C6A 107.33(9) . . ? C7A C1A C2A 109.91(9) . . ? C6A C1A C2A 111.73(9) . . ? C7A C1A C5A 113.86(9) . . ? C6A C1A C5A 112.36(9) . . ? C2A C1A C5A 101.66(9) . . ? C3A C2A C1A 103.47(9) . . ? C3A C2A H2A1 111.1 . . ? C1A C2A H2A1 111.1 . . ? C3A C2A H2A2 111.1 . . ? C1A C2A H2A2 111.1 . . ? H2A1 C2A H2A2 109 . . ? C2A C3A C4A 105.07(10) . . ? C2A C3A H3A1 110.7 . . ? C4A C3A H3A1 110.7 . . ? C2A C3A H3A2 110.7 . . ? C4A C3A H3A2 110.7 . . ? H3A1 C3A H3A2 108.8 . . ? C3A C4A C5A 105.98(10) . . ? C3A C4A H4A1 110.5 . . ? C5A C4A H4A1 110.5 . . ? C3A C4A H4A2 110.5 . . ? C5A C4A H4A2 110.5 . . ? H4A1 C4A H4A2 108.7 . . ? C4A C5A C1A 106.26(9) . . ? C4A C5A H5A1 110.5 . . ? C1A C5A H5A1 110.5 . . ? C4A C5A H5A2 110.5 . . ? C1A C5A H5A2 110.5 . . ? H5A1 C5A H5A2 108.7 . . ? O1A C6A N1A 121.72(11) . . ? O1A C6A C1A 121.50(10) . . ? N1A C6A C1A 116.78(10) . . ? C8A C7A C12A 117.60(11) . . ? C8A C7A C1A 119.23(10) . . ? C12A C7A C1A 123.16(11) . . ? C9A C8A C7A 121.55(13) . . ? C9A C8A H8A 119.2 . . ? C7A C8A H8A 119.2 . . ? C10A C9A C8A 120.22(14) . . ? C10A C9A H9A 119.9 . . ? C8A C9A H9A 119.9 . . ? C9A C10A C11A 119.27(13) . . ? C9A C10A H10A 120.4 . . ? C11A C10A H10A 120.4 . . ? C10A C11A C12A 120.68(14) . . ? C10A C11A H11A 119.7 . . ? C12A C11A H11A 119.7 . . ? C7A C12A C11A 120.67(14) . . ? C7A C12A H12A 119.7 . . ? C11A C12A H12A 119.7 . . ? C6A N1A H1As 119.2(9) . . ? C6A N1A H1Aa 121.3(10) . . ? H1As N1A H1Aa 118.8(13) . . ? 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 C7A C1A C2A C3A 79.08(11) . . . . ? C6A C1A C2A C3A -161.88(10) . . . . ? C5A C1A C2A C3A -41.86(11) . . . . ? C1A C2A C3A C4A 36.63(12) . . . . ? C2A C3A C4A C5A -16.56(13) . . . . ? C3A C4A C5A C1A -9.69(13) . . . . ? C7A C1A C5A C4A -86.51(12) . . . . ? C6A C1A C5A C4A 151.19(10) . . . . ? C2A C1A C5A C4A 31.61(12) . . . . ? C7A C1A C6A O1A 97.52(12) . . . . ? C2A C1A C6A O1A -23.04(15) . . . . ? C5A C1A C6A O1A -136.56(11) . . . . ? C7A C1A C6A N1A -81.55(12) . . . . ? C2A C1A C6A N1A 157.89(10) . . . . ? C5A C1A C6A N1A 44.37(13) . . . . ? C6A C1A C7A C8A -43.63(14) . . . . ? C2A C1A C7A C8A 78.07(13) . . . . ? C5A C1A C7A C8A -168.65(11) . . . . ? C6A C1A C7A C12A 137.49(12) . . . . ? C2A C1A C7A C12A -100.80(13) . . . . ? C5A C1A C7A C12A 12.47(16) . . . . ? C12A C7A C8A C9A 0.2(2) . . . . ? C1A C7A C8A C9A -178.73(13) . . . . ? C7A C8A C9A C10A -0.2(2) . . . . ? C8A C9A C10A C11A -0.1(2) . . . . ? C9A C10A C11A C12A 0.3(2) . . . . ? C8A C7A C12A C11A 0.1(2) . . . . ? C1A C7A C12A C11A 178.96(12) . . . . ? C10A C11A C12A C7A -0.4(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1A H1As O1A 0.914(17) 2.145(17) 3.0471(14) 169.2(13) 3_676 N1A H1Aa O1A 0.894(16) 2.230(17) 3.1040(14) 165.6(13) 4_575 ### END data_2 _database_code_depnum_ccdc_archive 'CCDC 649369' _audit_creation_date 2007-01-15T15:29:52-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 1-Phenylcyclohexanecarboxamide ; _chemical_formula_moiety 'C13 H17 N O' _chemical_formula_sum 'C13 H17 N O' _chemical_formula_weight 203.28 _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pca2(1) _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 13.8232(19) _cell_length_b 6.1326(8) _cell_length_c 26.176(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2219.0(5) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1009 _cell_measurement_theta_min 3.322 _cell_measurement_theta_max 27.9 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.14 _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 3 0 0.07 0 0 -1 0.2 0 0 1 0.2 4 -3 0 0.08 -3 -2 1 0.05 1 0 1 0.18 -1 0 -1 0.18 1 0 -1 0.18 -1 0 1 0.18 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 1999)' _exptl_absorpt_correction_T_min 0.9764 _exptl_absorpt_correction_T_max 0.9917 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 1999) ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_av_R_equivalents 0.0691 _diffrn_reflns_av_unetI/netI 0.0346 _diffrn_reflns_number 21897 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 2731 _reflns_number_gt 2282 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART-NT (Bruker, 1998)' _computing_cell_refinement 'Bruker SAINT+ (Bruker, 1999)' _computing_data_reduction 'Bruker SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0655P)^2^+0.3177P] 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_number_reflns 2731 _refine_ls_number_parameters 287 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1126 _refine_ls_wR_factor_gt 0.1058 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881, 2392 Friedel Pairs' _refine_ls_abs_structure_Flack -10(10) _refine_diff_density_max 0.217 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.04 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1A C 0.77826(16) 0.3486(4) 0.36849(9) 0.0202(5) Uani 1 1 d . . . C1B C 0.48031(17) 0.1715(4) 0.14438(9) 0.0210(5) Uani 1 1 d . . . C2A C 0.83677(18) 0.1458(4) 0.38555(10) 0.0251(5) Uani 1 1 d . . . H2A1 H 0.8639 0.1731 0.42 0.03 Uiso 1 1 calc R . . H2A2 H 0.7924 0.0195 0.3881 0.03 Uiso 1 1 calc R . . C2B C 0.41948(18) 0.3717(4) 0.12862(10) 0.0253(6) Uani 1 1 d . . . H2B1 H 0.4624 0.5007 0.1266 0.03 Uiso 1 1 calc R . . H2B2 H 0.3925 0.3461 0.0941 0.03 Uiso 1 1 calc R . . C3A C 0.91943(18) 0.0882(5) 0.34903(11) 0.0282(6) Uani 1 1 d . . . H3A1 H 0.8921 0.0418 0.3158 0.034 Uiso 1 1 calc R . . H3A2 H 0.9567 -0.0356 0.3632 0.034 Uiso 1 1 calc R . . C3B C 0.33653(18) 0.4217(5) 0.16533(11) 0.0288(6) Uani 1 1 d . . . H3B1 H 0.3634 0.4661 0.1988 0.035 Uiso 1 1 calc R . . H3B2 H 0.2981 0.545 0.1518 0.035 Uiso 1 1 calc R . . C4A C 0.9314(2) 0.4812(5) 0.32268(14) 0.0319(7) Uani 1 1 d . . . H4A1 H 0.9027 0.4514 0.2887 0.038 Uiso 1 1 calc R . . H4A2 H 0.9761 0.6064 0.3192 0.038 Uiso 1 1 calc R . . C4B C 0.27082(19) 0.2248(5) 0.17266(12) 0.0346(6) Uani 1 1 d . . . H4B1 H 0.237 0.1921 0.1402 0.042 Uiso 1 1 calc R . . H4B2 H 0.2214 0.2585 0.1988 0.042 Uiso 1 1 calc R . . C5A C 0.85035(19) 0.5396(5) 0.36087(12) 0.0251(6) Uani 1 1 d . . . H5A1 H 0.8148 0.6689 0.3482 0.03 Uiso 1 1 calc R . . H5A2 H 0.8796 0.5781 0.3942 0.03 Uiso 1 1 calc R . . C5B C 0.3292(2) 0.0266(5) 0.18933(14) 0.0330(7) Uani 1 1 d . . . H5B1 H 0.2859 -0.1015 0.192 0.04 Uiso 1 1 calc R . . H5B2 H 0.3575 0.0539 0.2235 0.04 Uiso 1 1 calc R . . C6A C 0.98747(19) 0.2821(5) 0.34057(11) 0.0318(6) Uani 1 1 d . . . H6A1 H 1.0214 0.3166 0.3729 0.038 Uiso 1 1 calc R . . H6A2 H 1.0367 0.2431 0.3147 0.038 Uiso 1 1 calc R . . C6B C 0.41065(19) -0.0228(4) 0.15109(12) 0.0258(6) Uani 1 1 d . . . H6B1 H 0.3819 -0.0599 0.1176 0.031 Uiso 1 1 calc R . . H6B2 H 0.4477 -0.1511 0.1631 0.031 Uiso 1 1 calc R . . C7A C 0.72155(18) 0.2973(4) 0.31874(10) 0.0257(6) Uani 1 1 d . . . C7B C 0.53661(18) 0.2216(5) 0.19445(10) 0.0258(6) Uani 1 1 d . . . C8A C 0.69937(16) 0.3974(4) 0.40898(10) 0.0212(5) Uani 1 1 d . . . C8B C 0.55957(17) 0.1324(4) 0.10353(9) 0.0233(5) Uani 1 1 d . . . C9A C 0.62789(18) 0.2409(4) 0.41826(10) 0.0260(6) Uani 1 1 d . . . H9A H 0.6284 0.1083 0.3995 0.031 Uiso 1 1 calc R . . C9B C 0.62778(19) 0.2964(4) 0.09400(11) 0.0296(6) Uani 1 1 d . . . H9B H 0.6249 0.4288 0.1128 0.036 Uiso 1 1 calc R . . C10A C 0.55606(19) 0.2762(5) 0.45457(11) 0.0318(6) Uani 1 1 d . . . H10A H 0.5083 0.1677 0.4605 0.038 Uiso 1 1 calc R . . C10B C 0.7000(2) 0.2679(5) 0.05724(12) 0.0358(7) Uani 1 1 d . . . H10B H 0.7456 0.3808 0.0512 0.043 Uiso 1 1 calc R . . C11A C 0.5540(2) 0.4699(5) 0.48218(12) 0.0336(7) Uani 1 1 d . . . H11A H 0.5046 0.4949 0.5067 0.04 Uiso 1 1 calc R . . C11B C 0.7055(2) 0.0766(5) 0.02957(11) 0.0350(7) Uani 1 1 d . . . H11B H 0.7543 0.0579 0.0044 0.042 Uiso 1 1 calc R . . C12A C 0.6244(2) 0.6259(5) 0.47367(11) 0.0324(6) Uani 1 1 d . . . H12A H 0.6237 0.7581 0.4926 0.039 Uiso 1 1 calc R . . C12B C 0.6388(2) -0.0881(5) 0.03886(12) 0.0348(7) Uani 1 1 d . . . H12B H 0.6427 -0.2209 0.0203 0.042 Uiso 1 1 calc R . . C13A C 0.69691(18) 0.5895(5) 0.43714(11) 0.0271(6) Uani 1 1 d . . . H13A H 0.745 0.6976 0.4316 0.033 Uiso 1 1 calc R . . C13B C 0.5658(2) -0.0601(5) 0.07539(11) 0.0285(6) Uani 1 1 d . . . H13B H 0.5202 -0.1733 0.081 0.034 Uiso 1 1 calc R . . N1A N 0.69479(19) 0.4692(5) 0.29064(11) 0.0329(6) Uani 1 1 d . . . N1B N 0.56560(19) 0.0500(5) 0.22210(11) 0.0353(6) Uani 1 1 d . . . O1A O 0.70020(14) 0.1083(3) 0.30702(8) 0.0343(5) Uani 1 1 d . . . O1B O 0.55720(14) 0.4112(3) 0.20645(8) 0.0343(5) Uani 1 1 d . . . H1As H 0.655(3) 0.440(6) 0.2670(17) 0.050(10) Uiso 1 1 d . . . H1Aa H 0.707(2) 0.607(6) 0.2993(14) 0.042(10) Uiso 1 1 d . . . H1Bs H 0.605(3) 0.060(7) 0.2536(18) 0.066(12) Uiso 1 1 d . . . H1Ba H 0.553(2) -0.084(6) 0.2109(13) 0.029(8) 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 C1A 0.0194(11) 0.0218(12) 0.0193(12) -0.0005(9) -0.0016(9) -0.0012(9) C1B 0.0207(12) 0.0218(12) 0.0203(12) -0.0006(9) -0.0006(9) -0.0004(9) C2A 0.0231(12) 0.0249(13) 0.0271(13) 0.0024(11) -0.0013(10) 0.0007(10) C2B 0.0280(13) 0.0258(13) 0.0222(13) -0.0003(10) -0.0016(10) 0.0003(10) C3A 0.0240(13) 0.0272(14) 0.0335(15) -0.0023(12) -0.0013(11) 0.0033(10) C3B 0.0238(12) 0.0307(14) 0.0319(14) -0.0046(12) -0.0016(11) 0.0024(11) C4A 0.0259(14) 0.0320(15) 0.0377(19) 0.0002(12) 0.0092(12) -0.0071(11) C4B 0.0242(13) 0.0417(16) 0.0379(16) -0.0108(14) 0.0013(11) -0.0018(11) C5A 0.0244(12) 0.0230(13) 0.0278(15) 0.0013(11) 0.0005(10) -0.0042(10) C5B 0.0331(15) 0.0309(15) 0.0350(18) -0.0032(12) 0.0089(12) -0.0081(12) C6A 0.0209(13) 0.0354(15) 0.0392(17) -0.0072(13) 0.0035(11) -0.0033(11) C6B 0.0264(12) 0.0238(13) 0.0274(15) -0.0022(11) 0.0037(11) -0.0019(10) C7A 0.0185(12) 0.0381(15) 0.0205(12) 0.0004(11) 0.0015(9) 0.0003(10) C7B 0.0184(11) 0.0377(15) 0.0212(12) -0.0028(11) -0.0001(9) 0.0029(10) C8A 0.0187(11) 0.0258(13) 0.0190(12) 0.0030(10) -0.0022(9) -0.0001(9) C8B 0.0226(12) 0.0287(13) 0.0186(13) 0.0010(10) -0.0039(9) 0.0003(10) C9A 0.0258(13) 0.0274(13) 0.0248(13) -0.0008(10) -0.0010(10) -0.0023(10) C9B 0.0280(14) 0.0309(14) 0.0301(14) -0.0018(12) 0.0013(11) -0.0031(11) C10A 0.0234(13) 0.0422(17) 0.0297(15) 0.0060(13) 0.0037(10) -0.0055(11) C10B 0.0294(14) 0.0427(17) 0.0354(16) 0.0063(13) 0.0035(11) -0.0065(12) C11A 0.0300(14) 0.0454(17) 0.0255(16) -0.0008(12) 0.0042(12) 0.0035(13) C11B 0.0260(14) 0.0566(19) 0.0225(14) 0.0031(14) 0.0041(10) 0.0046(14) C12A 0.0384(15) 0.0347(15) 0.0241(13) -0.0053(11) 0.0024(11) 0.0011(12) C12B 0.0335(15) 0.0439(17) 0.0268(14) -0.0073(13) 0.0012(12) 0.0026(13) C13A 0.0267(13) 0.0304(15) 0.0243(14) -0.0013(11) 0.0000(10) -0.0043(11) C13B 0.0273(14) 0.0313(15) 0.0268(15) -0.0021(11) 0.0028(10) -0.0029(11) N1A 0.0320(13) 0.0406(15) 0.0262(15) 0.0013(11) -0.0101(11) 0.0043(11) N1B 0.0357(14) 0.0409(15) 0.0292(15) 0.0012(12) -0.0088(11) 0.0035(12) O1A 0.0348(11) 0.0387(12) 0.0293(11) -0.0061(9) -0.0070(8) -0.0063(9) O1B 0.0337(11) 0.0393(12) 0.0300(11) -0.0069(9) -0.0086(8) -0.0058(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1A C2A 1.549(3) . ? C1A C8A 1.550(3) . ? C1A C5A 1.551(4) . ? C1A C7A 1.552(3) . ? C1B C6B 1.542(4) . ? C1B C2B 1.544(3) . ? C1B C8B 1.550(3) . ? C1B C7B 1.555(3) . ? C2A C3A 1.531(4) . ? C2A H2A1 0.99 . ? C2A H2A2 0.99 . ? C2B C3B 1.527(4) . ? C2B H2B1 0.99 . ? C2B H2B2 0.99 . ? C3A C6A 1.532(4) . ? C3A H3A1 0.99 . ? C3A H3A2 0.99 . ? C3B C4B 1.523(4) . ? C3B H3B1 0.99 . ? C3B H3B2 0.99 . ? C4A C6A 1.520(4) . ? C4A C5A 1.544(4) . ? C4A H4A1 0.99 . ? C4A H4A2 0.99 . ? C4B C5B 1.523(4) . ? C4B H4B1 0.99 . ? C4B H4B2 0.99 . ? C5A H5A1 0.99 . ? C5A H5A2 0.99 . ? C5B C6B 1.537(4) . ? C5B H5B1 0.99 . ? C5B H5B2 0.99 . ? C6A H6A1 0.99 . ? C6A H6A2 0.99 . ? C6B H6B1 0.99 . ? C6B H6B2 0.99 . ? C7A O1A 1.235(3) . ? C7A N1A 1.338(4) . ? C7B O1B 1.238(3) . ? C7B N1B 1.339(4) . ? C8A C13A 1.390(4) . ? C8A C9A 1.399(3) . ? C8B C13B 1.394(4) . ? C8B C9B 1.401(4) . ? C9A C10A 1.392(4) . ? C9A H9A 0.95 . ? C9B C10B 1.398(4) . ? C9B H9B 0.95 . ? C10A C11A 1.391(4) . ? C10A H10A 0.95 . ? C10B C11B 1.380(4) . ? C10B H10B 0.95 . ? C11A C12A 1.383(4) . ? C11A H11A 0.95 . ? C11B C12B 1.389(4) . ? C11B H11B 0.95 . ? C12A C13A 1.403(4) . ? C12A H12A 0.95 . ? C12B C13B 1.400(4) . ? C12B H12B 0.95 . ? C13A H13A 0.95 . ? C13B H13B 0.95 . ? N1A H1As 0.85(4) . ? N1A H1Aa 0.89(4) . ? N1B H1Bs 0.99(5) . ? N1B H1Ba 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 C2A C1A C8A 109.0(2) . . ? C2A C1A C5A 107.9(2) . . ? C8A C1A C5A 113.2(2) . . ? C2A C1A C7A 110.0(2) . . ? C8A C1A C7A 104.93(18) . . ? C5A C1A C7A 111.7(2) . . ? C6B C1B C2B 107.8(2) . . ? C6B C1B C8B 113.6(2) . . ? C2B C1B C8B 108.9(2) . . ? C6B C1B C7B 111.7(2) . . ? C2B C1B C7B 109.9(2) . . ? C8B C1B C7B 104.97(18) . . ? C3A C2A C1A 113.2(2) . . ? C3A C2A H2A1 108.9 . . ? C1A C2A H2A1 108.9 . . ? C3A C2A H2A2 108.9 . . ? C1A C2A H2A2 108.9 . . ? H2A1 C2A H2A2 107.7 . . ? C3B C2B C1B 113.6(2) . . ? C3B C2B H2B1 108.8 . . ? C1B C2B H2B1 108.8 . . ? C3B C2B H2B2 108.8 . . ? C1B C2B H2B2 108.8 . . ? H2B1 C2B H2B2 107.7 . . ? C2A C3A C6A 111.7(2) . . ? C2A C3A H3A1 109.3 . . ? C6A C3A H3A1 109.3 . . ? C2A C3A H3A2 109.3 . . ? C6A C3A H3A2 109.3 . . ? H3A1 C3A H3A2 107.9 . . ? C4B C3B C2B 111.6(2) . . ? C4B C3B H3B1 109.3 . . ? C2B C3B H3B1 109.3 . . ? C4B C3B H3B2 109.3 . . ? C2B C3B H3B2 109.3 . . ? H3B1 C3B H3B2 108 . . ? C6A C4A C5A 110.9(3) . . ? C6A C4A H4A1 109.5 . . ? C5A C4A H4A1 109.5 . . ? C6A C4A H4A2 109.5 . . ? C5A C4A H4A2 109.5 . . ? H4A1 C4A H4A2 108 . . ? C3B C4B C5B 110.7(2) . . ? C3B C4B H4B1 109.5 . . ? C5B C4B H4B1 109.5 . . ? C3B C4B H4B2 109.5 . . ? C5B C4B H4B2 109.5 . . ? H4B1 C4B H4B2 108.1 . . ? C4A C5A C1A 112.0(2) . . ? C4A C5A H5A1 109.2 . . ? C1A C5A H5A1 109.2 . . ? C4A C5A H5A2 109.2 . . ? C1A C5A H5A2 109.2 . . ? H5A1 C5A H5A2 107.9 . . ? C4B C5B C6B 111.0(3) . . ? C4B C5B H5B1 109.4 . . ? C6B C5B H5B1 109.4 . . ? C4B C5B H5B2 109.4 . . ? C6B C5B H5B2 109.4 . . ? H5B1 C5B H5B2 108 . . ? C4A C6A C3A 110.8(2) . . ? C4A C6A H6A1 109.5 . . ? C3A C6A H6A1 109.5 . . ? C4A C6A H6A2 109.5 . . ? C3A C6A H6A2 109.5 . . ? H6A1 C6A H6A2 108.1 . . ? C5B C6B C1B 112.3(2) . . ? C5B C6B H6B1 109.1 . . ? C1B C6B H6B1 109.1 . . ? C5B C6B H6B2 109.1 . . ? C1B C6B H6B2 109.1 . . ? H6B1 C6B H6B2 107.9 . . ? O1A C7A N1A 122.5(3) . . ? O1A C7A C1A 121.3(2) . . ? N1A C7A C1A 116.2(2) . . ? O1B C7B N1B 122.2(3) . . ? O1B C7B C1B 121.0(2) . . ? N1B C7B C1B 116.7(2) . . ? C13A C8A C9A 118.2(2) . . ? C13A C8A C1A 122.9(2) . . ? C9A C8A C1A 118.9(2) . . ? C13B C8B C9B 118.2(2) . . ? C13B C8B C1B 122.7(2) . . ? C9B C8B C1B 119.2(2) . . ? C10A C9A C8A 121.0(3) . . ? C10A C9A H9A 119.5 . . ? C8A C9A H9A 119.5 . . ? C10B C9B C8B 120.9(3) . . ? C10B C9B H9B 119.6 . . ? C8B C9B H9B 119.6 . . ? C11A C10A C9A 120.2(3) . . ? C11A C10A H10A 119.9 . . ? C9A C10A H10A 119.9 . . ? C11B C10B C9B 120.5(3) . . ? C11B C10B H10B 119.8 . . ? C9B C10B H10B 119.8 . . ? C12A C11A C10A 119.5(3) . . ? C12A C11A H11A 120.2 . . ? C10A C11A H11A 120.2 . . ? C10B C11B C12B 119.3(3) . . ? C10B C11B H11B 120.3 . . ? C12B C11B H11B 120.3 . . ? C11A C12A C13A 120.2(3) . . ? C11A C12A H12A 119.9 . . ? C13A C12A H12A 119.9 . . ? C11B C12B C13B 120.5(3) . . ? C11B C12B H12B 119.7 . . ? C13B C12B H12B 119.7 . . ? C8A C13A C12A 120.9(2) . . ? C8A C13A H13A 119.5 . . ? C12A C13A H13A 119.5 . . ? C8B C13B C12B 120.6(3) . . ? C8B C13B H13B 119.7 . . ? C12B C13B H13B 119.7 . . ? C7A N1A H1As 114(3) . . ? C7A N1A H1Aa 124(2) . . ? H1As N1A H1Aa 121(4) . . ? C7B N1B H1Bs 125(3) . . ? C7B N1B H1Ba 119(2) . . ? H1Bs N1B H1Ba 116(3) . . ? 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 C8A C1A C2A C3A -177.9(2) . . . . ? C5A C1A C2A C3A -54.5(3) . . . . ? C7A C1A C2A C3A 67.6(3) . . . . ? C6B C1B C2B C3B 54.5(3) . . . . ? C8B C1B C2B C3B 178.1(2) . . . . ? C7B C1B C2B C3B -67.4(3) . . . . ? C1A C2A C3A C6A 55.0(3) . . . . ? C1B C2B C3B C4B -55.2(3) . . . . ? C2B C3B C4B C5B 54.3(3) . . . . ? C6A C4A C5A C1A -58.5(3) . . . . ? C2A C1A C5A C4A 56.0(3) . . . . ? C8A C1A C5A C4A 176.7(2) . . . . ? C7A C1A C5A C4A -65.1(3) . . . . ? C3B C4B C5B C6B -55.9(3) . . . . ? C5A C4A C6A C3A 56.2(3) . . . . ? C2A C3A C6A C4A -54.5(3) . . . . ? C4B C5B C6B C1B 58.2(3) . . . . ? C2B C1B C6B C5B -55.7(3) . . . . ? C8B C1B C6B C5B -176.4(2) . . . . ? C7B C1B C6B C5B 65.2(3) . . . . ? C2A C1A C7A O1A 23.7(3) . . . . ? C8A C1A C7A O1A -93.4(3) . . . . ? C5A C1A C7A O1A 143.6(3) . . . . ? C2A C1A C7A N1A -158.5(2) . . . . ? C8A C1A C7A N1A 84.4(3) . . . . ? C5A C1A C7A N1A -38.6(3) . . . . ? C6B C1B C7B O1B -144.7(3) . . . . ? C2B C1B C7B O1B -25.2(3) . . . . ? C8B C1B C7B O1B 91.7(3) . . . . ? C6B C1B C7B N1B 38.6(3) . . . . ? C2B C1B C7B N1B 158.1(2) . . . . ? C8B C1B C7B N1B -84.9(3) . . . . ? C2A C1A C8A C13A 117.2(3) . . . . ? C5A C1A C8A C13A -2.9(3) . . . . ? C7A C1A C8A C13A -124.9(3) . . . . ? C2A C1A C8A C9A -62.0(3) . . . . ? C5A C1A C8A C9A 177.9(2) . . . . ? C7A C1A C8A C9A 55.9(3) . . . . ? C6B C1B C8B C13B 0.7(3) . . . . ? C2B C1B C8B C13B -119.4(3) . . . . ? C7B C1B C8B C13B 122.9(3) . . . . ? C6B C1B C8B C9B -179.7(2) . . . . ? C2B C1B C8B C9B 60.3(3) . . . . ? C7B C1B C8B C9B -57.4(3) . . . . ? C13A C8A C9A C10A 0.1(4) . . . . ? C1A C8A C9A C10A 179.4(2) . . . . ? C13B C8B C9B C10B 0.1(4) . . . . ? C1B C8B C9B C10B -179.6(2) . . . . ? C8A C9A C10A C11A 0.4(4) . . . . ? C8B C9B C10B C11B -0.1(4) . . . . ? C9A C10A C11A C12A -0.7(4) . . . . ? C9B C10B C11B C12B -0.4(4) . . . . ? C10A C11A C12A C13A 0.5(4) . . . . ? C10B C11B C12B C13B 0.9(4) . . . . ? C9A C8A C13A C12A -0.3(4) . . . . ? C1A C8A C13A C12A -179.6(2) . . . . ? C11A C12A C13A C8A 0.0(4) . . . . ? C9B C8B C13B C12B 0.3(4) . . . . ? C1B C8B C13B C12B -180.0(2) . . . . ? C11B C12B C13B C8B -0.8(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1B H1Bs O1A 0.99(5) 1.95(4) 2.921(3) 169(4) . N1A H1As O1B 0.85(4) 2.09(4) 2.933(3) 172(4) . ### END data_3 _database_code_depnum_ccdc_archive 'CCDC 649370' _audit_creation_date 2007-01-15T15:55:21-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 1-(2-Fluorophenyl)cyclohexanecarbocamide ; _chemical_formula_moiety 'C13 H16 F N O' _chemical_formula_sum 'C13 H16 F N O' _chemical_formula_weight 221.27 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.792(5) _cell_length_b 8.646(4) _cell_length_c 12.170(5) _cell_angle_alpha 90 _cell_angle_beta 111.510(7) _cell_angle_gamma 90 _cell_volume 1154.4(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 946 _cell_measurement_theta_min 2.965 _cell_measurement_theta_max 27.757 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 0 0 0.04 1 0 0 0.04 0 1 0 0.16 0 -1 0 0.16 -1 1 1 0.15 1 0 -3 0.2 -1 0 3 0.2 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 1999)' _exptl_absorpt_correction_T_min 0.9681 _exptl_absorpt_correction_T_max 0.9927 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 1999) ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SMART 1 K CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_av_R_equivalents 0.0803 _diffrn_reflns_av_unetI/netI 0.051 _diffrn_reflns_number 12323 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 2791 _reflns_number_gt 2003 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART-NT (Bruker, 1998)' _computing_cell_refinement 'Bruker SAINT+ (Bruker, 1999)' _computing_data_reduction 'Bruker SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0615P)^2^+0.0696P] 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_number_reflns 2791 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0654 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1186 _refine_ls_wR_factor_gt 0.109 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.301 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.043 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1A C 0.69295(11) 0.52657(14) 0.30698(11) 0.0229(3) Uani 1 1 d . . . C2A C 0.78067(12) 0.38573(14) 0.34220(11) 0.0273(3) Uani 1 1 d . . . H2A1 H 0.7331 0.2895 0.3147 0.033 Uiso 1 1 calc R . . H2A2 H 0.84 0.3938 0.3022 0.033 Uiso 1 1 calc R . . C3A C 0.84969(12) 0.37591(16) 0.47531(12) 0.0325(3) Uani 1 1 d . . . H3A1 H 0.906 0.2865 0.4935 0.039 Uiso 1 1 calc R . . H3A2 H 0.8989 0.4708 0.503 0.039 Uiso 1 1 calc R . . C4A C 0.76198(14) 0.35808(17) 0.53988(13) 0.0389(4) Uani 1 1 d . . . H4A1 H 0.8084 0.3544 0.6261 0.047 Uiso 1 1 calc R . . H4A2 H 0.7165 0.2597 0.5161 0.047 Uiso 1 1 calc R . . C5A C 0.67248(14) 0.49314(17) 0.51110(13) 0.0363(3) Uani 1 1 d . . . H5A1 H 0.7172 0.5891 0.5455 0.044 Uiso 1 1 calc R . . H5A2 H 0.6115 0.4746 0.5479 0.044 Uiso 1 1 calc R . . C6A C 0.60632(12) 0.51532(16) 0.37729(12) 0.0296(3) Uani 1 1 d . . . H6A1 H 0.5568 0.6109 0.3636 0.036 Uiso 1 1 calc R . . H6A2 H 0.5498 0.4275 0.3459 0.036 Uiso 1 1 calc R . . C7A C 0.60864(11) 0.51097(14) 0.17566(11) 0.0262(3) Uani 1 1 d . . . C8A C 0.76318(10) 0.68041(14) 0.32631(10) 0.0232(3) Uani 1 1 d . . . C9A C 0.84691(11) 0.71001(15) 0.27230(11) 0.0281(3) Uani 1 1 d . . . C10A C 0.91171(12) 0.84528(17) 0.28423(13) 0.0365(3) Uani 1 1 d . . . H10A H 0.9681 0.858 0.2457 0.044 Uiso 1 1 calc R . . C11A C 0.89327(15) 0.96230(18) 0.35319(14) 0.0416(4) Uani 1 1 d . . . H11A H 0.9378 1.0563 0.3637 0.05 Uiso 1 1 calc R . . C12A C 0.80971(16) 0.94126(18) 0.40651(13) 0.0446(4) Uani 1 1 d . . . H12A H 0.7959 1.0219 0.4531 0.054 Uiso 1 1 calc R . . C13A C 0.74518(13) 0.80314(16) 0.39289(12) 0.0351(3) Uani 1 1 d . . . H13A H 0.6873 0.792 0.4299 0.042 Uiso 1 1 calc R . . N1A N 0.56923(12) 0.64139(14) 0.11445(11) 0.0357(3) Uani 1 1 d . . . O1A O 0.57573(10) 0.38253(11) 0.13161(9) 0.0411(3) Uani 1 1 d . . . F1A F 0.86356(8) 0.60018(10) 0.19879(8) 0.0442(3) Uani 1 1 d . . . H1As H 0.5207(17) 0.636(2) 0.0402(18) 0.053 Uiso 1 1 d . . . H1Aa H 0.5975(16) 0.730(2) 0.1470(16) 0.053 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 C1A 0.0226(6) 0.0246(6) 0.0217(6) -0.0015(5) 0.0084(5) -0.0007(5) C2A 0.0277(6) 0.0259(7) 0.0278(6) 0.0015(5) 0.0097(5) 0.0027(5) C3A 0.0308(7) 0.0309(7) 0.0306(7) 0.0039(5) 0.0050(6) 0.0016(5) C4A 0.0482(9) 0.0398(8) 0.0273(7) 0.0049(6) 0.0122(6) -0.0050(7) C5A 0.0410(8) 0.0430(8) 0.0316(7) 0.0003(6) 0.0213(6) -0.0043(6) C6A 0.0263(6) 0.0320(7) 0.0342(7) -0.0010(5) 0.0154(6) -0.0036(5) C7A 0.0230(6) 0.0284(7) 0.0265(7) -0.0019(5) 0.0082(5) 0.0002(5) C8A 0.0220(6) 0.0255(6) 0.0206(6) 0.0014(5) 0.0063(5) 0.0003(5) C9A 0.0252(6) 0.0324(7) 0.0270(6) 0.0042(5) 0.0098(5) 0.0033(5) C10A 0.0261(7) 0.0434(8) 0.0384(8) 0.0125(6) 0.0098(6) -0.0043(6) C11A 0.0446(8) 0.0349(8) 0.0357(8) 0.0055(6) 0.0033(7) -0.0143(6) C12A 0.0667(11) 0.0301(8) 0.0367(8) -0.0065(6) 0.0185(8) -0.0099(7) C13A 0.0468(8) 0.0298(7) 0.0343(7) -0.0039(6) 0.0215(7) -0.0038(6) N1A 0.0383(7) 0.0269(6) 0.0295(6) -0.0022(5) -0.0021(5) 0.0017(5) O1A 0.0529(6) 0.0269(5) 0.0308(5) -0.0036(4) 0.0002(5) -0.0054(4) F1A 0.0537(5) 0.0436(5) 0.0515(5) -0.0001(4) 0.0383(5) 0.0045(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1A C8A 1.5386(17) . ? C1A C7A 1.5478(18) . ? C1A C2A 1.5529(17) . ? C1A C6A 1.5577(18) . ? C2A C3A 1.5255(19) . ? C2A H2A1 0.99 . ? C2A H2A2 0.99 . ? C3A C4A 1.519(2) . ? C3A H3A1 0.99 . ? C3A H3A2 0.99 . ? C4A C5A 1.526(2) . ? C4A H4A1 0.99 . ? C4A H4A2 0.99 . ? C5A C6A 1.538(2) . ? C5A H5A1 0.99 . ? C5A H5A2 0.99 . ? C6A H6A1 0.99 . ? C6A H6A2 0.99 . ? C7A O1A 1.2323(16) . ? C7A N1A 1.3374(18) . ? C8A C9A 1.3959(18) . ? C8A C13A 1.3977(19) . ? C9A F1A 1.3673(16) . ? C9A C10A 1.3752(19) . ? C10A C11A 1.382(2) . ? C10A H10A 0.95 . ? C11A C12A 1.376(2) . ? C11A H11A 0.95 . ? C12A C13A 1.393(2) . ? C12A H12A 0.95 . ? C13A H13A 0.95 . ? N1A H1As 0.88(2) . ? N1A H1Aa 0.872(19) . ? 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 C8A C1A C7A 109.83(10) . . ? C8A C1A C2A 111.65(10) . . ? C7A C1A C2A 109.11(10) . . ? C8A C1A C6A 113.25(10) . . ? C7A C1A C6A 105.04(10) . . ? C2A C1A C6A 107.70(10) . . ? C3A C2A C1A 112.26(10) . . ? C3A C2A H2A1 109.2 . . ? C1A C2A H2A1 109.2 . . ? C3A C2A H2A2 109.2 . . ? C1A C2A H2A2 109.2 . . ? H2A1 C2A H2A2 107.9 . . ? C4A C3A C2A 110.83(11) . . ? C4A C3A H3A1 109.5 . . ? C2A C3A H3A1 109.5 . . ? C4A C3A H3A2 109.5 . . ? C2A C3A H3A2 109.5 . . ? H3A1 C3A H3A2 108.1 . . ? C3A C4A C5A 110.39(12) . . ? C3A C4A H4A1 109.6 . . ? C5A C4A H4A1 109.6 . . ? C3A C4A H4A2 109.6 . . ? C5A C4A H4A2 109.6 . . ? H4A1 C4A H4A2 108.1 . . ? C4A C5A C6A 112.21(11) . . ? C4A C5A H5A1 109.2 . . ? C6A C5A H5A1 109.2 . . ? C4A C5A H5A2 109.2 . . ? C6A C5A H5A2 109.2 . . ? H5A1 C5A H5A2 107.9 . . ? C5A C6A C1A 114.15(11) . . ? C5A C6A H6A1 108.7 . . ? C1A C6A H6A1 108.7 . . ? C5A C6A H6A2 108.7 . . ? C1A C6A H6A2 108.7 . . ? H6A1 C6A H6A2 107.6 . . ? O1A C7A N1A 121.85(12) . . ? O1A C7A C1A 120.56(11) . . ? N1A C7A C1A 117.52(11) . . ? C9A C8A C13A 114.70(12) . . ? C9A C8A C1A 121.37(11) . . ? C13A C8A C1A 123.86(11) . . ? F1A C9A C10A 116.88(12) . . ? F1A C9A C8A 118.48(11) . . ? C10A C9A C8A 124.60(13) . . ? C9A C10A C11A 118.80(14) . . ? C9A C10A H10A 120.6 . . ? C11A C10A H10A 120.6 . . ? C12A C11A C10A 119.27(14) . . ? C12A C11A H11A 120.4 . . ? C10A C11A H11A 120.4 . . ? C11A C12A C13A 120.77(15) . . ? C11A C12A H12A 119.6 . . ? C13A C12A H12A 119.6 . . ? C12A C13A C8A 121.83(14) . . ? C12A C13A H13A 119.1 . . ? C8A C13A H13A 119.1 . . ? C7A N1A H1As 119.7(11) . . ? C7A N1A H1Aa 119.5(12) . . ? H1As N1A H1Aa 120.6(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8A C1A C2A C3A 69.47(13) . . . . ? C7A C1A C2A C3A -168.95(10) . . . . ? C6A C1A C2A C3A -55.45(13) . . . . ? C1A C2A C3A C4A 60.70(14) . . . . ? C2A C3A C4A C5A -57.94(15) . . . . ? C3A C4A C5A C6A 53.61(16) . . . . ? C4A C5A C6A C1A -52.13(15) . . . . ? C8A C1A C6A C5A -72.56(14) . . . . ? C7A C1A C6A C5A 167.60(11) . . . . ? C2A C1A C6A C5A 51.39(14) . . . . ? C8A C1A C7A O1A 155.82(12) . . . . ? C2A C1A C7A O1A 33.15(17) . . . . ? C6A C1A C7A O1A -82.08(15) . . . . ? C8A C1A C7A N1A -27.08(16) . . . . ? C2A C1A C7A N1A -149.76(12) . . . . ? C6A C1A C7A N1A 95.01(14) . . . . ? C7A C1A C8A C9A -64.22(14) . . . . ? C2A C1A C8A C9A 56.94(15) . . . . ? C6A C1A C8A C9A 178.71(11) . . . . ? C7A C1A C8A C13A 112.53(13) . . . . ? C2A C1A C8A C13A -126.31(13) . . . . ? C6A C1A C8A C13A -4.55(17) . . . . ? C13A C8A C9A F1A -175.47(11) . . . . ? C1A C8A C9A F1A 1.56(17) . . . . ? C13A C8A C9A C10A 2.10(18) . . . . ? C1A C8A C9A C10A 179.12(11) . . . . ? F1A C9A C10A C11A 176.95(12) . . . . ? C8A C9A C10A C11A -0.7(2) . . . . ? C9A C10A C11A C12A -0.9(2) . . . . ? C10A C11A C12A C13A 0.8(2) . . . . ? C11A C12A C13A C8A 0.7(2) . . . . ? C9A C8A C13A C12A -2.1(2) . . . . ? C1A C8A C13A C12A -179.03(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1A H1As O1A 0.88(2) 1.99(2) 2.8598(19) 174.5(17) 3_665 ### END data_4 _database_code_depnum_ccdc_archive 'CCDC 649371' _audit_creation_date 2007-01-15T16:09:53-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 1-(2-Chlorophenyl)cyclohexanecarboxamide ; _chemical_formula_moiety 'C13 H16 Cl N O' _chemical_formula_sum 'C13 H16 Cl N O' _chemical_formula_weight 237.72 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.314(2) _cell_length_b 9.3311(13) _cell_length_c 29.104(4) _cell_angle_alpha 90 _cell_angle_beta 90.109(10) _cell_angle_gamma 90 _cell_volume 3615.6(9) _cell_formula_units_Z 12 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 963 _cell_measurement_theta_min 2.593 _cell_measurement_theta_max 27.896 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.31 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1512 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 -1 0.1 0 0 1 0.1 -1 0 0 0.13 1 0 0 0.13 -1 -1 1 0.24 0 1 0 0.28 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.295 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 1999)' _exptl_absorpt_correction_T_min 0.8738 _exptl_absorpt_correction_T_max 0.9466 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 1999) ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_av_R_equivalents 0.0905 _diffrn_reflns_av_unetI/netI 0.0616 _diffrn_reflns_number 39540 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.4 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 8724 _reflns_number_gt 6264 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART-NT (Bruker, 1998)' _computing_cell_refinement 'Bruker SAINT+ (Bruker, 1999)' _computing_data_reduction 'Bruker SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.1494P)^2^+3.3154P] 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_number_reflns 8724 _refine_ls_number_parameters 451 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0737 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1576 _refine_ls_wR_factor_gt 0.1339 _refine_ls_goodness_of_fit_ref 0.662 _refine_ls_restrained_S_all 0.662 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.444 _refine_diff_density_min -0.42 _refine_diff_density_rms 0.053 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 C1A C 0.39554(14) 0.3932(2) 0.20037(7) 0.0235(4) Uani 1 1 d . . . C2A C 0.32725(16) 0.5176(2) 0.18354(8) 0.0312(5) Uani 1 1 d . . . H2A1 H 0.3631 0.6095 0.188 0.037 Uiso 1 1 calc R . . H2A2 H 0.3146 0.5058 0.1502 0.037 Uiso 1 1 calc R . . C3A C 0.22660(16) 0.5243(3) 0.20862(8) 0.0355(5) Uani 1 1 d . . . H3A1 H 0.1861 0.6042 0.196 0.043 Uiso 1 1 calc R . . H3A2 H 0.1892 0.4341 0.2033 0.043 Uiso 1 1 calc R . . C4A C 0.24122(19) 0.5462(3) 0.25996(9) 0.0451(6) Uani 1 1 d . . . H4A1 H 0.1752 0.5478 0.2755 0.054 Uiso 1 1 calc R . . H4A2 H 0.275 0.6391 0.2657 0.054 Uiso 1 1 calc R . . C5A C 0.30492(19) 0.4246(3) 0.27901(8) 0.0455(6) Uani 1 1 d . . . H5A1 H 0.267 0.3337 0.2765 0.055 Uiso 1 1 calc R . . H5A2 H 0.3185 0.4424 0.312 0.055 Uiso 1 1 calc R . . C6A C 0.40542(16) 0.4093(3) 0.25334(8) 0.0350(5) Uani 1 1 d . . . H6A1 H 0.4413 0.3245 0.2656 0.042 Uiso 1 1 calc R . . H6A2 H 0.4472 0.4946 0.26 0.042 Uiso 1 1 calc R . . C7A C 0.50382(14) 0.4152(2) 0.18258(7) 0.0261(4) Uani 1 1 d . . . C8A C 0.35745(14) 0.2446(2) 0.18573(7) 0.0248(4) Uani 1 1 d . . . C9A C 0.34454(15) 0.2048(2) 0.13952(8) 0.0307(5) Uani 1 1 d . . . C10A C 0.31230(17) 0.0696(3) 0.12625(11) 0.0482(7) Uani 1 1 d . . . H10A H 0.3029 0.0486 0.0946 0.058 Uiso 1 1 calc R . . C11A C 0.29387(19) -0.0340(3) 0.15860(14) 0.0577(9) Uani 1 1 d . . . H11A H 0.2712 -0.1264 0.1496 0.069 Uiso 1 1 calc R . . C12A C 0.3087(2) -0.0019(3) 0.20417(13) 0.0570(9) Uani 1 1 d . . . H12A H 0.2976 -0.0734 0.2268 0.068 Uiso 1 1 calc R . . C13A C 0.33962(16) 0.1344(3) 0.21741(9) 0.0371(5) Uani 1 1 d . . . H13A H 0.3491 0.1535 0.2492 0.044 Uiso 1 1 calc R . . N1A N 0.56348(13) 0.2988(2) 0.18277(7) 0.0292(4) Uani 1 1 d . . . H1As H 0.624(2) 0.301(3) 0.1740(9) 0.035 Uiso 1 1 d . . . H1Aa H 0.538(2) 0.215(3) 0.1903(9) 0.035 Uiso 1 1 d . . . O1A O 0.53595(12) 0.53388(17) 0.17165(7) 0.0432(4) Uani 1 1 d . . . Cl1A Cl 0.37472(5) 0.32106(8) 0.094551(19) 0.04535(18) Uani 1 1 d . . . C1B C 0.91630(13) 0.45284(19) 0.12754(6) 0.0197(4) Uani 1 1 d . . . C2B C 0.97979(14) 0.3334(2) 0.15087(7) 0.0241(4) Uani 1 1 d . . . H2B1 H 0.9912 0.3595 0.1834 0.029 Uiso 1 1 calc R . . H2B2 H 0.9412 0.2427 0.1503 0.029 Uiso 1 1 calc R . . C3B C 1.08103(15) 0.3091(2) 0.12777(8) 0.0316(5) Uani 1 1 d . . . H3B1 H 1.1211 0.3983 0.1293 0.038 Uiso 1 1 calc R . . H3B2 H 1.1183 0.2333 0.1444 0.038 Uiso 1 1 calc R . . C4B C 1.06741(17) 0.2651(3) 0.07797(9) 0.0387(5) Uani 1 1 d . . . H4B1 H 1.1338 0.2478 0.0638 0.046 Uiso 1 1 calc R . . H4B2 H 1.0283 0.1749 0.0764 0.046 Uiso 1 1 calc R . . C5B C 1.01269(17) 0.3823(3) 0.05193(8) 0.0347(5) Uani 1 1 d . . . H5B1 H 0.9995 0.3497 0.0201 0.042 Uiso 1 1 calc R . . H5B2 H 1.056 0.4684 0.0503 0.042 Uiso 1 1 calc R . . C6B C 0.91265(15) 0.4224(2) 0.07488(7) 0.0270(4) Uani 1 1 d . . . H6B1 H 0.8644 0.3434 0.0694 0.032 Uiso 1 1 calc R . . H6B2 H 0.8858 0.5086 0.0593 0.032 Uiso 1 1 calc R . . C7B C 0.80463(13) 0.4383(2) 0.14175(7) 0.0210(4) Uani 1 1 d . . . C8B C 0.95688(13) 0.60177(19) 0.13995(6) 0.0186(4) Uani 1 1 d . . . C9B C 0.95356(14) 0.6565(2) 0.18476(7) 0.0225(4) Uani 1 1 d . . . C10B C 0.99058(16) 0.7904(2) 0.19645(7) 0.0286(4) Uani 1 1 d . . . H10B H 0.9866 0.8228 0.2273 0.034 Uiso 1 1 calc R . . C11B C 1.03345(16) 0.8770(2) 0.16317(8) 0.0307(5) Uani 1 1 d . . . H11B H 1.0598 0.9684 0.171 0.037 Uiso 1 1 calc R . . C12B C 1.03714(16) 0.8281(2) 0.11842(8) 0.0305(5) Uani 1 1 d . . . H12B H 1.0662 0.8862 0.0952 0.037 Uiso 1 1 calc R . . C13B C 0.99837(14) 0.6942(2) 0.10738(7) 0.0239(4) Uani 1 1 d . . . H13B H 1.0002 0.6641 0.0762 0.029 Uiso 1 1 calc R . . Cl1B Cl 0.89722(4) 0.56079(6) 0.229622(17) 0.03291(14) Uani 1 1 d . . . N1B N 0.74711(13) 0.55336(19) 0.13654(7) 0.0270(4) Uani 1 1 d . . . H1Bs H 0.683(2) 0.549(3) 0.1439(9) 0.032 Uiso 1 1 d . . . H1Ba H 0.7704(19) 0.630(3) 0.1269(9) 0.032 Uiso 1 1 d . . . O1B O 0.77017(10) 0.32123(15) 0.15456(5) 0.0285(3) Uani 1 1 d . . . C1C C 0.66648(13) -0.00815(19) 0.05945(6) 0.0189(4) Uani 1 1 d . . . C2C C 0.63178(15) -0.1112(2) 0.02077(7) 0.0249(4) Uani 1 1 d . . . H2C1 H 0.5808 -0.0613 0.0018 0.03 Uiso 1 1 calc R . . H2C2 H 0.69 -0.1319 0.0007 0.03 Uiso 1 1 calc R . . C3C C 0.58740(17) -0.2534(2) 0.03709(8) 0.0323(5) Uani 1 1 d . . . H3C1 H 0.5581 -0.3044 0.0104 0.039 Uiso 1 1 calc R . . H3C2 H 0.642 -0.3138 0.0497 0.039 Uiso 1 1 calc R . . C4C C 0.50691(18) -0.2348(3) 0.07353(9) 0.0400(6) Uani 1 1 d . . . H4C1 H 0.486 -0.3299 0.0852 0.048 Uiso 1 1 calc R . . H4C2 H 0.4473 -0.1876 0.0599 0.048 Uiso 1 1 calc R . . C5C C 0.54711(16) -0.1441(2) 0.11315(8) 0.0321(5) Uani 1 1 d . . . H5C1 H 0.6048 -0.1933 0.1277 0.039 Uiso 1 1 calc R . . H5C2 H 0.4941 -0.1315 0.1366 0.039 Uiso 1 1 calc R . . C6C C 0.58033(15) 0.0023(2) 0.09520(7) 0.0252(4) Uani 1 1 d . . . H6C1 H 0.6031 0.0618 0.1214 0.03 Uiso 1 1 calc R . . H6C2 H 0.522 0.0509 0.0809 0.03 Uiso 1 1 calc R . . C7C C 0.75895(14) -0.0673(2) 0.08536(7) 0.0209(4) Uani 1 1 d . . . C8C C 0.69013(14) 0.1375(2) 0.03751(7) 0.0217(4) Uani 1 1 d . . . C9C C 0.76742(17) 0.1583(2) 0.00562(7) 0.0280(4) Uani 1 1 d . . . C10C C 0.7792(2) 0.2861(3) -0.01832(8) 0.0384(6) Uani 1 1 d . . . H10C H 0.8309 0.2952 -0.0406 0.046 Uiso 1 1 calc R . . C11C C 0.7157(2) 0.3999(3) -0.00964(10) 0.0469(7) Uani 1 1 d . . . H11C H 0.7228 0.4872 -0.0261 0.056 Uiso 1 1 calc R . . C12C C 0.64210(19) 0.3855(2) 0.02302(10) 0.0430(6) Uani 1 1 d . . . H12C H 0.5995 0.4643 0.0298 0.052 Uiso 1 1 calc R . . C13C C 0.62966(16) 0.2572(2) 0.04605(8) 0.0300(5) Uani 1 1 d . . . H13C H 0.5782 0.2501 0.0685 0.036 Uiso 1 1 calc R . . Cl1C Cl 0.85743(5) 0.02547(7) -0.00458(2) 0.04028(16) Uani 1 1 d . . . N1C N 0.80482(14) 0.0249(2) 0.11389(6) 0.0263(4) Uani 1 1 d . . . H1Ca H 0.7832(19) 0.111(3) 0.1196(9) 0.032 Uiso 1 1 d . . . H1Cs H 0.855(2) -0.007(3) 0.1283(9) 0.032 Uiso 1 1 d . . . O1C O 0.78587(11) -0.19261(14) 0.08178(5) 0.0296(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1A 0.0154(8) 0.0318(10) 0.0234(9) -0.0014(8) 0.0002(7) 0.0018(7) C2A 0.0241(10) 0.0323(11) 0.0371(12) -0.0018(9) -0.0011(9) 0.0075(8) C3A 0.0218(10) 0.0475(13) 0.0371(12) -0.0119(10) -0.0039(9) 0.0091(9) C4A 0.0290(12) 0.0646(17) 0.0416(14) -0.0250(12) 0.0024(10) 0.0075(11) C5A 0.0358(13) 0.0782(19) 0.0223(11) -0.0144(11) 0.0010(10) 0.0086(12) C6A 0.0241(10) 0.0546(14) 0.0263(11) -0.0098(10) -0.0050(8) 0.0039(10) C7A 0.0154(9) 0.0303(10) 0.0325(11) 0.0003(8) -0.0008(8) 0.0010(7) C8A 0.0126(8) 0.0327(11) 0.0291(10) -0.0012(8) 0.0019(7) 0.0020(7) C9A 0.0147(9) 0.0425(12) 0.0350(12) -0.0089(9) -0.0023(8) 0.0067(8) C10A 0.0224(11) 0.0564(16) 0.0658(18) -0.0340(14) -0.0072(11) 0.0062(11) C11A 0.0258(12) 0.0417(15) 0.106(3) -0.0276(17) 0.0096(14) -0.0055(10) C12A 0.0332(13) 0.0351(13) 0.103(3) 0.0105(15) 0.0264(15) -0.0005(10) C13A 0.0256(11) 0.0390(12) 0.0466(14) 0.0047(10) 0.0108(10) 0.0024(9) N1A 0.0151(8) 0.0276(9) 0.0450(11) 0.0039(8) 0.0048(7) 0.0006(7) O1A 0.0259(8) 0.0302(8) 0.0736(13) 0.0101(8) 0.0108(8) 0.0006(6) Cl1A 0.0412(3) 0.0730(4) 0.0218(3) -0.0010(3) -0.0006(2) 0.0195(3) C1B 0.0157(8) 0.0214(9) 0.0220(9) 0.0012(7) -0.0022(7) -0.0009(7) C2B 0.0172(9) 0.0233(9) 0.0317(10) 0.0009(8) -0.0029(8) 0.0035(7) C3B 0.0196(10) 0.0328(11) 0.0423(13) -0.0079(9) -0.0030(9) 0.0066(8) C4B 0.0272(11) 0.0417(13) 0.0473(14) -0.0172(11) 0.0070(10) 0.0015(9) C5B 0.0333(11) 0.0425(13) 0.0283(11) -0.0123(9) 0.0058(9) -0.0074(10) C6B 0.0236(10) 0.0331(11) 0.0242(10) -0.0034(8) -0.0035(8) -0.0064(8) C7B 0.0146(8) 0.0241(9) 0.0244(9) 0.0041(7) -0.0016(7) -0.0008(7) C8B 0.0099(8) 0.0231(9) 0.0227(9) 0.0015(7) -0.0017(7) 0.0019(6) C9B 0.0172(8) 0.0284(10) 0.0220(9) 0.0016(7) -0.0010(7) 0.0019(7) C10B 0.0273(10) 0.0322(11) 0.0261(10) -0.0072(8) -0.0019(8) 0.0004(8) C11B 0.0239(10) 0.0263(10) 0.0418(12) -0.0067(9) -0.0016(9) -0.0051(8) C12B 0.0262(10) 0.0285(10) 0.0368(12) 0.0028(9) 0.0047(9) -0.0063(8) C13B 0.0207(9) 0.0290(10) 0.0219(9) 0.0015(7) 0.0005(7) -0.0022(7) Cl1B 0.0397(3) 0.0374(3) 0.0216(2) 0.0050(2) 0.0062(2) 0.0013(2) N1B 0.0146(8) 0.0233(9) 0.0431(11) 0.0099(7) 0.0005(7) 0.0012(6) O1B 0.0187(7) 0.0237(7) 0.0432(9) 0.0083(6) 0.0038(6) -0.0012(5) C1C 0.0180(8) 0.0175(8) 0.0212(9) -0.0005(7) -0.0036(7) 0.0020(6) C2C 0.0273(10) 0.0209(9) 0.0263(10) -0.0027(8) -0.0075(8) 0.0019(7) C3C 0.0373(12) 0.0208(10) 0.0389(12) -0.0006(8) -0.0179(10) -0.0027(8) C4C 0.0341(12) 0.0340(12) 0.0518(15) 0.0129(11) -0.0151(11) -0.0126(10) C5C 0.0219(10) 0.0389(12) 0.0355(12) 0.0085(9) 0.0013(9) -0.0028(8) C6C 0.0211(9) 0.0273(10) 0.0273(10) -0.0010(8) -0.0019(8) 0.0029(7) C7C 0.0183(9) 0.0215(9) 0.0229(9) 0.0051(7) 0.0006(7) 0.0000(7) C8C 0.0244(9) 0.0194(9) 0.0212(9) 0.0004(7) -0.0090(7) 0.0016(7) C9C 0.0353(11) 0.0257(10) 0.0229(10) 0.0025(8) -0.0058(8) -0.0037(8) C10C 0.0469(14) 0.0390(13) 0.0292(11) 0.0118(9) -0.0115(10) -0.0151(11) C11C 0.0538(16) 0.0259(12) 0.0608(16) 0.0202(11) -0.0315(13) -0.0134(11) C12C 0.0409(13) 0.0172(10) 0.0708(18) 0.0031(11) -0.0267(13) 0.0009(9) C13C 0.0279(10) 0.0204(10) 0.0417(12) -0.0018(8) -0.0107(9) 0.0037(8) Cl1C 0.0405(3) 0.0420(3) 0.0385(3) 0.0012(2) 0.0174(2) 0.0049(2) N1C 0.0231(9) 0.0287(9) 0.0270(9) 0.0015(7) -0.0075(7) 0.0008(7) O1C 0.0257(7) 0.0188(7) 0.0443(9) 0.0061(6) -0.0066(6) 0.0041(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1A C8A 1.536(3) . ? C1A C7A 1.546(3) . ? C1A C2A 1.553(3) . ? C1A C6A 1.554(3) . ? C2A C3A 1.528(3) . ? C2A H2A1 0.99 . ? C2A H2A2 0.99 . ? C3A C4A 1.520(3) . ? C3A H3A1 0.99 . ? C3A H3A2 0.99 . ? C4A C5A 1.521(4) . ? C4A H4A1 0.99 . ? C4A H4A2 0.99 . ? C5A C6A 1.540(3) . ? C5A H5A1 0.99 . ? C5A H5A2 0.99 . ? C6A H6A1 0.99 . ? C6A H6A2 0.99 . ? C7A O1A 1.229(3) . ? C7A N1A 1.346(3) . ? C8A C13A 1.402(3) . ? C8A C9A 1.406(3) . ? C9A C10A 1.387(3) . ? C9A Cl1A 1.747(2) . ? C10A C11A 1.372(5) . ? C10A H10A 0.95 . ? C11A C12A 1.373(5) . ? C11A H11A 0.95 . ? C12A C13A 1.391(4) . ? C12A H12A 0.95 . ? C13A H13A 0.95 . ? N1A H1As 0.85(3) . ? N1A H1Aa 0.88(3) . ? C1B C8B 1.534(3) . ? C1B C7B 1.550(3) . ? C1B C2B 1.554(3) . ? C1B C6B 1.559(3) . ? C2B C3B 1.524(3) . ? C2B H2B1 0.99 . ? C2B H2B2 0.99 . ? C3B C4B 1.517(3) . ? C3B H3B1 0.99 . ? C3B H3B2 0.99 . ? C4B C5B 1.517(4) . ? C4B H4B1 0.99 . ? C4B H4B2 0.99 . ? C5B C6B 1.537(3) . ? C5B H5B1 0.99 . ? C5B H5B2 0.99 . ? C6B H6B1 0.99 . ? C6B H6B2 0.99 . ? C7B O1B 1.242(2) . ? C7B N1B 1.328(2) . ? C8B C13B 1.396(3) . ? C8B C9B 1.401(3) . ? C9B C10B 1.385(3) . ? C9B Cl1B 1.752(2) . ? C10B C11B 1.385(3) . ? C10B H10B 0.95 . ? C11B C12B 1.381(3) . ? C11B H11B 0.95 . ? C12B C13B 1.390(3) . ? C12B H12B 0.95 . ? C13B H13B 0.95 . ? N1B H1Bs 0.88(3) . ? N1B H1Ba 0.83(3) . ? C1C C8C 1.534(3) . ? C1C C7C 1.545(2) . ? C1C C2C 1.550(3) . ? C1C C6C 1.553(3) . ? C2C C3C 1.529(3) . ? C2C H2C1 0.99 . ? C2C H2C2 0.99 . ? C3C C4C 1.519(4) . ? C3C H3C1 0.99 . ? C3C H3C2 0.99 . ? C4C C5C 1.527(3) . ? C4C H4C1 0.99 . ? C4C H4C2 0.99 . ? C5C C6C 1.528(3) . ? C5C H5C1 0.99 . ? C5C H5C2 0.99 . ? C6C H6C1 0.99 . ? C6C H6C2 0.99 . ? C7C O1C 1.227(2) . ? C7C N1C 1.342(3) . ? C8C C13C 1.400(3) . ? C8C C9C 1.401(3) . ? C9C C10C 1.390(3) . ? C9C Cl1C 1.750(2) . ? C10C C11C 1.381(4) . ? C10C H10C 0.95 . ? C11C C12C 1.373(4) . ? C11C H11C 0.95 . ? C12C C13C 1.382(3) . ? C12C H12C 0.95 . ? C13C H13C 0.95 . ? N1C H1Ca 0.87(3) . ? N1C H1Cs 0.84(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 C8A C1A C7A 109.54(16) . . ? C8A C1A C2A 113.21(16) . . ? C7A C1A C2A 109.94(17) . . ? C8A C1A C6A 112.91(18) . . ? C7A C1A C6A 104.01(16) . . ? C2A C1A C6A 106.81(17) . . ? C3A C2A C1A 113.17(19) . . ? C3A C2A H2A1 108.9 . . ? C1A C2A H2A1 108.9 . . ? C3A C2A H2A2 108.9 . . ? C1A C2A H2A2 108.9 . . ? H2A1 C2A H2A2 107.8 . . ? C4A C3A C2A 111.36(19) . . ? C4A C3A H3A1 109.4 . . ? C2A C3A H3A1 109.4 . . ? C4A C3A H3A2 109.4 . . ? C2A C3A H3A2 109.4 . . ? H3A1 C3A H3A2 108 . . ? C3A C4A C5A 109.17(19) . . ? C3A C4A H4A1 109.8 . . ? C5A C4A H4A1 109.8 . . ? C3A C4A H4A2 109.8 . . ? C5A C4A H4A2 109.8 . . ? H4A1 C4A H4A2 108.3 . . ? C4A C5A C6A 112.1(2) . . ? C4A C5A H5A1 109.2 . . ? C6A C5A H5A1 109.2 . . ? C4A C5A H5A2 109.2 . . ? C6A C5A H5A2 109.2 . . ? H5A1 C5A H5A2 107.9 . . ? C5A C6A C1A 114.71(18) . . ? C5A C6A H6A1 108.6 . . ? C1A C6A H6A1 108.6 . . ? C5A C6A H6A2 108.6 . . ? C1A C6A H6A2 108.6 . . ? H6A1 C6A H6A2 107.6 . . ? O1A C7A N1A 121.51(19) . . ? O1A C7A C1A 122.09(18) . . ? N1A C7A C1A 116.23(18) . . ? C13A C8A C9A 114.5(2) . . ? C13A C8A C1A 122.42(19) . . ? C9A C8A C1A 122.93(19) . . ? C10A C9A C8A 123.0(2) . . ? C10A C9A Cl1A 115.3(2) . . ? C8A C9A Cl1A 121.65(17) . . ? C11A C10A C9A 120.3(3) . . ? C11A C10A H10A 119.8 . . ? C9A C10A H10A 119.8 . . ? C10A C11A C12A 119.0(3) . . ? C10A C11A H11A 120.5 . . ? C12A C11A H11A 120.5 . . ? C11A C12A C13A 120.6(3) . . ? C11A C12A H12A 119.7 . . ? C13A C12A H12A 119.7 . . ? C12A C13A C8A 122.6(3) . . ? C12A C13A H13A 118.7 . . ? C8A C13A H13A 118.7 . . ? C7A N1A H1As 123.0(17) . . ? C7A N1A H1Aa 119.4(17) . . ? H1As N1A H1Aa 117(2) . . ? C8B C1B C7B 110.75(15) . . ? C8B C1B C2B 110.84(15) . . ? C7B C1B C2B 109.97(15) . . ? C8B C1B C6B 114.01(15) . . ? C7B C1B C6B 102.60(15) . . ? C2B C1B C6B 108.34(16) . . ? C3B C2B C1B 113.23(17) . . ? C3B C2B H2B1 108.9 . . ? C1B C2B H2B1 108.9 . . ? C3B C2B H2B2 108.9 . . ? C1B C2B H2B2 108.9 . . ? H2B1 C2B H2B2 107.7 . . ? C4B C3B C2B 110.95(18) . . ? C4B C3B H3B1 109.4 . . ? C2B C3B H3B1 109.4 . . ? C4B C3B H3B2 109.4 . . ? C2B C3B H3B2 109.4 . . ? H3B1 C3B H3B2 108 . . ? C5B C4B C3B 109.78(18) . . ? C5B C4B H4B1 109.7 . . ? C3B C4B H4B1 109.7 . . ? C5B C4B H4B2 109.7 . . ? C3B C4B H4B2 109.7 . . ? H4B1 C4B H4B2 108.2 . . ? C4B C5B C6B 111.96(19) . . ? C4B C5B H5B1 109.2 . . ? C6B C5B H5B1 109.2 . . ? C4B C5B H5B2 109.2 . . ? C6B C5B H5B2 109.2 . . ? H5B1 C5B H5B2 107.9 . . ? C5B C6B C1B 116.48(17) . . ? C5B C6B H6B1 108.2 . . ? C1B C6B H6B1 108.2 . . ? C5B C6B H6B2 108.2 . . ? C1B C6B H6B2 108.2 . . ? H6B1 C6B H6B2 107.3 . . ? O1B C7B N1B 122.16(17) . . ? O1B C7B C1B 120.82(16) . . ? N1B C7B C1B 116.86(16) . . ? C13B C8B C9B 114.84(17) . . ? C13B C8B C1B 122.63(17) . . ? C9B C8B C1B 122.52(16) . . ? C10B C9B C8B 123.05(18) . . ? C10B C9B Cl1B 115.42(15) . . ? C8B C9B Cl1B 121.48(15) . . ? C9B C10B C11B 120.08(19) . . ? C9B C10B H10B 120 . . ? C11B C10B H10B 120 . . ? C12B C11B C10B 118.84(19) . . ? C12B C11B H11B 120.6 . . ? C10B C11B H11B 120.6 . . ? C11B C12B C13B 120.1(2) . . ? C11B C12B H12B 120 . . ? C13B C12B H12B 120 . . ? C12B C13B C8B 123.08(19) . . ? C12B C13B H13B 118.5 . . ? C8B C13B H13B 118.5 . . ? C7B N1B H1Bs 119.6(16) . . ? C7B N1B H1Ba 121.3(18) . . ? H1Bs N1B H1Ba 119(2) . . ? C8C C1C C7C 110.85(15) . . ? C8C C1C C2C 107.95(15) . . ? C7C C1C C2C 111.65(15) . . ? C8C C1C C6C 112.05(15) . . ? C7C C1C C6C 106.52(15) . . ? C2C C1C C6C 107.82(15) . . ? C3C C2C C1C 115.32(17) . . ? C3C C2C H2C1 108.4 . . ? C1C C2C H2C1 108.4 . . ? C3C C2C H2C2 108.4 . . ? C1C C2C H2C2 108.4 . . ? H2C1 C2C H2C2 107.5 . . ? C4C C3C C2C 113.03(18) . . ? C4C C3C H3C1 109 . . ? C2C C3C H3C1 109 . . ? C4C C3C H3C2 109 . . ? C2C C3C H3C2 109 . . ? H3C1 C3C H3C2 107.8 . . ? C3C C4C C5C 110.11(18) . . ? C3C C4C H4C1 109.6 . . ? C5C C4C H4C1 109.6 . . ? C3C C4C H4C2 109.6 . . ? C5C C4C H4C2 109.6 . . ? H4C1 C4C H4C2 108.2 . . ? C4C C5C C6C 109.81(18) . . ? C4C C5C H5C1 109.7 . . ? C6C C5C H5C1 109.7 . . ? C4C C5C H5C2 109.7 . . ? C6C C5C H5C2 109.7 . . ? H5C1 C5C H5C2 108.2 . . ? C5C C6C C1C 112.78(17) . . ? C5C C6C H6C1 109 . . ? C1C C6C H6C1 109 . . ? C5C C6C H6C2 109 . . ? C1C C6C H6C2 109 . . ? H6C1 C6C H6C2 107.8 . . ? O1C C7C N1C 122.07(18) . . ? O1C C7C C1C 122.13(17) . . ? N1C C7C C1C 115.71(17) . . ? C13C C8C C9C 115.48(18) . . ? C13C C8C C1C 120.98(18) . . ? C9C C8C C1C 123.39(17) . . ? C10C C9C C8C 122.3(2) . . ? C10C C9C Cl1C 116.40(18) . . ? C8C C9C Cl1C 121.22(15) . . ? C11C C10C C9C 119.9(2) . . ? C11C C10C H10C 120.1 . . ? C9C C10C H10C 120.1 . . ? C12C C11C C10C 119.3(2) . . ? C12C C11C H11C 120.3 . . ? C10C C11C H11C 120.3 . . ? C11C C12C C13C 120.4(2) . . ? C11C C12C H12C 119.8 . . ? C13C C12C H12C 119.8 . . ? C12C C13C C8C 122.4(2) . . ? C12C C13C H13C 118.8 . . ? C8C C13C H13C 118.8 . . ? C7C N1C H1Ca 124.1(17) . . ? C7C N1C H1Cs 116.1(17) . . ? H1Ca N1C H1Cs 120(2) . . ? 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 C8A C1A C2A C3A 71.0(2) . . . . ? C7A C1A C2A C3A -166.12(18) . . . . ? C6A C1A C2A C3A -53.9(2) . . . . ? C1A C2A C3A C4A 60.1(3) . . . . ? C2A C3A C4A C5A -58.1(3) . . . . ? C3A C4A C5A C6A 54.9(3) . . . . ? C4A C5A C6A C1A -54.1(3) . . . . ? C8A C1A C6A C5A -73.9(3) . . . . ? C7A C1A C6A C5A 167.4(2) . . . . ? C2A C1A C6A C5A 51.1(3) . . . . ? C8A C1A C7A O1A 148.2(2) . . . . ? C2A C1A C7A O1A 23.2(3) . . . . ? C6A C1A C7A O1A -90.9(3) . . . . ? C8A C1A C7A N1A -36.4(2) . . . . ? C2A C1A C7A N1A -161.36(19) . . . . ? C6A C1A C7A N1A 84.6(2) . . . . ? C7A C1A C8A C13A 112.0(2) . . . . ? C2A C1A C8A C13A -125.0(2) . . . . ? C6A C1A C8A C13A -3.4(3) . . . . ? C7A C1A C8A C9A -63.4(2) . . . . ? C2A C1A C8A C9A 59.7(2) . . . . ? C6A C1A C8A C9A -178.75(18) . . . . ? C13A C8A C9A C10A 2.9(3) . . . . ? C1A C8A C9A C10A 178.51(18) . . . . ? C13A C8A C9A Cl1A -173.74(15) . . . . ? C1A C8A C9A Cl1A 1.9(3) . . . . ? C8A C9A C10A C11A -1.7(3) . . . . ? Cl1A C9A C10A C11A 175.06(19) . . . . ? C9A C10A C11A C12A -0.5(4) . . . . ? C10A C11A C12A C13A 1.5(4) . . . . ? C11A C12A C13A C8A -0.2(4) . . . . ? C9A C8A C13A C12A -1.9(3) . . . . ? C1A C8A C13A C12A -177.6(2) . . . . ? C8B C1B C2B C3B -75.6(2) . . . . ? C7B C1B C2B C3B 161.56(16) . . . . ? C6B C1B C2B C3B 50.2(2) . . . . ? C1B C2B C3B C4B -60.1(2) . . . . ? C2B C3B C4B C5B 60.5(2) . . . . ? C3B C4B C5B C6B -54.6(2) . . . . ? C4B C5B C6B C1B 49.4(2) . . . . ? C8B C1B C6B C5B 78.4(2) . . . . ? C7B C1B C6B C5B -161.76(18) . . . . ? C2B C1B C6B C5B -45.5(2) . . . . ? C8B C1B C7B O1B -147.13(18) . . . . ? C2B C1B C7B O1B -24.3(2) . . . . ? C6B C1B C7B O1B 90.8(2) . . . . ? C8B C1B C7B N1B 37.3(2) . . . . ? C2B C1B C7B N1B 160.19(18) . . . . ? C6B C1B C7B N1B -84.7(2) . . . . ? C7B C1B C8B C13B -122.69(18) . . . . ? C2B C1B C8B C13B 114.96(19) . . . . ? C6B C1B C8B C13B -7.6(2) . . . . ? C7B C1B C8B C9B 56.2(2) . . . . ? C2B C1B C8B C9B -66.2(2) . . . . ? C6B C1B C8B C9B 171.28(17) . . . . ? C13B C8B C9B C10B -1.5(3) . . . . ? C1B C8B C9B C10B 179.53(17) . . . . ? C13B C8B C9B Cl1B 176.05(14) . . . . ? C1B C8B C9B Cl1B -2.9(2) . . . . ? C8B C9B C10B C11B 0.0(3) . . . . ? Cl1B C9B C10B C11B -177.74(16) . . . . ? C9B C10B C11B C12B 0.9(3) . . . . ? C10B C11B C12B C13B -0.1(3) . . . . ? C11B C12B C13B C8B -1.7(3) . . . . ? C9B C8B C13B C12B 2.4(3) . . . . ? C1B C8B C13B C12B -178.68(18) . . . . ? C8C C1C C2C C3C -169.71(17) . . . . ? C7C C1C C2C C3C 68.2(2) . . . . ? C6C C1C C2C C3C -48.5(2) . . . . ? C1C C2C C3C C4C 49.9(2) . . . . ? C2C C3C C4C C5C -53.3(2) . . . . ? C3C C4C C5C C6C 58.8(2) . . . . ? C4C C5C C6C C1C -61.5(2) . . . . ? C8C C1C C6C C5C 173.07(16) . . . . ? C7C C1C C6C C5C -65.6(2) . . . . ? C2C C1C C6C C5C 54.4(2) . . . . ? C8C C1C C7C O1C -134.91(19) . . . . ? C2C C1C C7C O1C -14.5(3) . . . . ? C6C C1C C7C O1C 102.9(2) . . . . ? C8C C1C C7C N1C 48.4(2) . . . . ? C2C C1C C7C N1C 168.84(17) . . . . ? C6C C1C C7C N1C -73.7(2) . . . . ? C7C C1C C8C C13C -126.24(19) . . . . ? C2C C1C C8C C13C 111.2(2) . . . . ? C6C C1C C8C C13C -7.4(2) . . . . ? C7C C1C C8C C9C 58.4(2) . . . . ? C2C C1C C8C C9C -64.2(2) . . . . ? C6C C1C C8C C9C 177.28(17) . . . . ? C13C C8C C9C C10C -4.2(3) . . . . ? C1C C8C C9C C10C 171.32(19) . . . . ? C13C C8C C9C Cl1C 173.41(15) . . . . ? C1C C8C C9C Cl1C -11.0(3) . . . . ? C8C C9C C10C C11C 2.5(3) . . . . ? Cl1C C9C C10C C11C -175.22(18) . . . . ? C9C C10C C11C C12C 0.7(3) . . . . ? C10C C11C C12C C13C -1.9(4) . . . . ? C11C C12C C13C C8C 0.0(3) . . . . ? C9C C8C C13C C12C 3.0(3) . . . . ? C1C C8C C13C C12C -172.69(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1A H1As O1B 0.85(3) 2.03(3) 2.881(2) 176(2) . N1B H1Bs O1A 0.88(3) 2.13(3) 2.999(2) 172(2) . N1B H1Ba O1C 0.83(3) 2.13(3) 2.903(2) 157(2) 1_565 N1C H1Ca O1B 0.87(3) 2.22(3) 3.043(2) 159(2) . ### END data_5 _database_code_depnum_ccdc_archive 'CCDC 649372' _audit_creation_date 2007-01-15T16:42:08-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 1-(2-Bromophenyl)cyclohexanecarboxamide ; _chemical_formula_moiety 'C13 H16 Br N O' _chemical_formula_sum 'C13 H16 Br N O' _chemical_formula_weight 282.18 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _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 8.9257(13) _cell_length_b 10.8387(16) _cell_length_c 13.7825(19) _cell_angle_alpha 69.877(10) _cell_angle_beta 87.223(11) _cell_angle_gamma 82.095(11) _cell_volume 1240.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 965 _cell_measurement_theta_min 2.792 _cell_measurement_theta_max 28.34 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.16 _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.08 0 0 -1 0.08 0 -1 -1 0.16 0 1 1 0.16 1 0 0 0.19 -1 0 0 0.19 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.294 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 1999)' _exptl_absorpt_correction_T_min 0.3418 _exptl_absorpt_correction_T_max 0.6224 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 1999) ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_av_R_equivalents 0.0634 _diffrn_reflns_av_unetI/netI 0.0495 _diffrn_reflns_number 17480 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 5986 _reflns_number_gt 4856 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART-NT (Bruker, 1998)' _computing_cell_refinement 'Bruker SAINT+ (Bruker, 1999)' _computing_data_reduction 'Bruker SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0899P)^2^+1.0151P] 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_number_reflns 5986 _refine_ls_number_parameters 301 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0958 _refine_ls_wR_factor_gt 0.088 _refine_ls_goodness_of_fit_ref 0.668 _refine_ls_restrained_S_all 0.668 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.43 _refine_diff_density_min -1.028 _refine_diff_density_rms 0.078 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 Br1A Br 0.62120(3) -0.23076(2) 0.30802(2) 0.04268(9) Uani 1 1 d . . . C1A C 0.5291(2) 0.09224(18) 0.21876(13) 0.0214(3) Uani 1 1 d . . . C2A C 0.4049(2) 0.0476(2) 0.16795(15) 0.0292(4) Uani 1 1 d . . . H2A1 H 0.4292 -0.0484 0.1799 0.035 Uiso 1 1 calc R . . H2A2 H 0.3067 0.0613 0.2018 0.035 Uiso 1 1 calc R . . C3A C 0.3891(3) 0.1225(3) 0.05168(17) 0.0453(6) Uani 1 1 d . . . H3A1 H 0.4853 0.1055 0.0168 0.054 Uiso 1 1 calc R . . H3A2 H 0.3089 0.0896 0.0237 0.054 Uiso 1 1 calc R . . C4A C 0.3498(3) 0.2707(3) 0.02928(19) 0.0560(8) Uani 1 1 d . . . H4A1 H 0.2517 0.2883 0.0618 0.067 Uiso 1 1 calc R . . H4A2 H 0.3402 0.3171 -0.0462 0.067 Uiso 1 1 calc R . . C5A C 0.4726(3) 0.3226(3) 0.07151(19) 0.0496(7) Uani 1 1 d . . . H5A1 H 0.4419 0.4175 0.0613 0.06 Uiso 1 1 calc R . . H5A2 H 0.5673 0.3153 0.0322 0.06 Uiso 1 1 calc R . . C6A C 0.5027(3) 0.2465(2) 0.18676(16) 0.0325(5) Uani 1 1 d . . . H6A1 H 0.4156 0.2712 0.2266 0.039 Uiso 1 1 calc R . . H6A2 H 0.5928 0.2759 0.2071 0.039 Uiso 1 1 calc R . . C7A C 0.5086(2) 0.04765(18) 0.33785(13) 0.0214(3) Uani 1 1 d . . . C8A C 0.6872(2) 0.0366(2) 0.19212(14) 0.0243(4) Uani 1 1 d . . . C9A C 0.7397(2) -0.0993(2) 0.22188(16) 0.0300(4) Uani 1 1 d . . . C10A C 0.8825(3) -0.1497(3) 0.19628(19) 0.0434(6) Uani 1 1 d . . . H10A H 0.9122 -0.2426 0.2177 0.052 Uiso 1 1 calc R . . C11A C 0.9801(3) -0.0632(3) 0.13956(19) 0.0497(7) Uani 1 1 d . . . H11A H 1.0771 -0.0963 0.1206 0.06 Uiso 1 1 calc R . . C12A C 0.9362(3) 0.0709(3) 0.11068(18) 0.0435(6) Uani 1 1 d . . . H12A H 1.0039 0.1308 0.0728 0.052 Uiso 1 1 calc R . . C13A C 0.7924(2) 0.1199(2) 0.13668(15) 0.0320(4) Uani 1 1 d . . . H13A H 0.7649 0.2131 0.116 0.038 Uiso 1 1 calc R . . N1A N 0.6275(2) 0.05111(18) 0.39171(13) 0.0270(3) Uani 1 1 d . . . O1A O 0.38556(16) 0.01905(15) 0.37933(10) 0.0283(3) Uani 1 1 d . . . H1As H 0.623(3) 0.037(3) 0.458(2) 0.034 Uiso 1 1 d . . . H1Aa H 0.704(3) 0.088(3) 0.359(2) 0.034 Uiso 1 1 d . . . Br1B Br 0.95042(3) 0.51004(2) 0.140370(16) 0.04179(9) Uani 1 1 d . . . C1B C 1.0200(2) 0.33144(18) 0.38673(13) 0.0208(3) Uani 1 1 d . . . C2B C 0.8820(2) 0.4249(2) 0.40538(15) 0.0265(4) Uani 1 1 d . . . H2B1 H 0.9193 0.4889 0.4321 0.032 Uiso 1 1 calc R . . H2B2 H 0.8324 0.476 0.3382 0.032 Uiso 1 1 calc R . . C3B C 0.7623(2) 0.3548(2) 0.48112(17) 0.0343(5) Uani 1 1 d . . . H3B1 H 0.6877 0.4223 0.4963 0.041 Uiso 1 1 calc R . . H3B2 H 0.7078 0.3063 0.4479 0.041 Uiso 1 1 calc R . . C4B C 0.8317(3) 0.2578(3) 0.58241(17) 0.0384(5) Uani 1 1 d . . . H4B1 H 0.871 0.3075 0.6218 0.046 Uiso 1 1 calc R . . H4B2 H 0.753 0.2074 0.6248 0.046 Uiso 1 1 calc R . . C5B C 0.9598(3) 0.1622(2) 0.56114(16) 0.0336(5) Uani 1 1 d . . . H5B1 H 0.9193 0.1085 0.5256 0.04 Uiso 1 1 calc R . . H5B2 H 1.005 0.1012 0.6273 0.04 Uiso 1 1 calc R . . C6B C 1.0811(2) 0.23799(19) 0.49393(14) 0.0263(4) Uani 1 1 d . . . H6B1 H 1.1655 0.1739 0.4841 0.032 Uiso 1 1 calc R . . H6B2 H 1.1215 0.291 0.5301 0.032 Uiso 1 1 calc R . . C7B C 0.9726(2) 0.24211(19) 0.33057(14) 0.0233(4) Uani 1 1 d . . . C8B C 1.1419(2) 0.41437(18) 0.32411(14) 0.0228(4) Uani 1 1 d . . . C9B C 1.1228(2) 0.4991(2) 0.22071(15) 0.0291(4) Uani 1 1 d . . . C10B C 1.2302(3) 0.5798(2) 0.16854(18) 0.0404(5) Uani 1 1 d . . . H10B H 1.2118 0.6374 0.0994 0.048 Uiso 1 1 calc R . . C11B C 1.3636(3) 0.5767(3) 0.2166(2) 0.0433(6) Uani 1 1 d . . . H11B H 1.4365 0.6325 0.1813 0.052 Uiso 1 1 calc R . . C12B C 1.3895(3) 0.4914(3) 0.31664(19) 0.0384(5) Uani 1 1 d . . . H12B H 1.4821 0.4865 0.3498 0.046 Uiso 1 1 calc R . . C13B C 1.2805(2) 0.4127(2) 0.36904(16) 0.0294(4) Uani 1 1 d . . . H13B H 1.3005 0.3554 0.4381 0.035 Uiso 1 1 calc R . . N1B N 1.0856(2) 0.16525(18) 0.30260(15) 0.0298(4) Uani 1 1 d . . . O1B O 0.83958(17) 0.23931(16) 0.31300(12) 0.0330(3) Uani 1 1 d . . . H1Bs H 1.052(3) 0.114(3) 0.275(2) 0.04 Uiso 1 1 d . . . H1Ba H 1.173(4) 0.153(3) 0.325(2) 0.04 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 Br1A 0.04813(16) 0.02413(11) 0.05438(16) -0.01102(10) -0.01542(11) -0.00091(9) C1A 0.0227(9) 0.0230(8) 0.0174(8) -0.0064(6) -0.0007(6) -0.0006(7) C2A 0.0246(10) 0.0406(11) 0.0234(9) -0.0128(8) -0.0057(7) -0.0005(8) C3A 0.0326(12) 0.0781(19) 0.0233(10) -0.0193(11) -0.0085(9) 0.0076(12) C4A 0.0441(15) 0.0718(19) 0.0274(11) 0.0040(11) -0.0034(10) 0.0209(13) C5A 0.0535(15) 0.0380(12) 0.0339(12) 0.0093(10) 0.0125(11) 0.0114(11) C6A 0.0389(12) 0.0229(9) 0.0289(10) -0.0032(8) 0.0102(8) 0.0008(8) C7A 0.0245(9) 0.0208(8) 0.0188(8) -0.0061(6) -0.0007(6) -0.0037(7) C8A 0.0248(9) 0.0319(9) 0.0201(8) -0.0149(7) -0.0027(7) 0.0002(7) C9A 0.0310(11) 0.0348(10) 0.0284(9) -0.0177(8) -0.0086(8) 0.0028(8) C10A 0.0399(13) 0.0543(14) 0.0426(12) -0.0323(11) -0.0138(10) 0.0184(11) C11A 0.0295(12) 0.089(2) 0.0399(13) -0.0413(14) -0.0037(10) 0.0120(13) C12A 0.0296(12) 0.0790(19) 0.0290(10) -0.0273(12) 0.0067(9) -0.0100(12) C13A 0.0307(11) 0.0457(12) 0.0230(9) -0.0157(9) 0.0033(8) -0.0072(9) N1A 0.0249(8) 0.0401(9) 0.0189(7) -0.0114(7) 0.0001(6) -0.0101(7) O1A 0.0233(7) 0.0388(8) 0.0211(6) -0.0064(6) 0.0009(5) -0.0091(6) Br1B 0.04651(15) 0.04766(15) 0.02616(12) -0.00593(9) -0.01471(9) -0.00160(11) C1B 0.0201(8) 0.0212(8) 0.0213(8) -0.0075(7) -0.0039(6) -0.0018(7) C2B 0.0251(9) 0.0275(9) 0.0292(9) -0.0142(8) -0.0052(7) 0.0027(7) C3B 0.0262(11) 0.0455(12) 0.0383(11) -0.0244(10) 0.0040(8) -0.0035(9) C4B 0.0410(13) 0.0466(13) 0.0316(10) -0.0163(10) 0.0096(9) -0.0144(10) C5B 0.0434(13) 0.0302(10) 0.0254(9) -0.0051(8) 0.0010(8) -0.0106(9) C6B 0.0290(10) 0.0249(9) 0.0233(9) -0.0062(7) -0.0052(7) -0.0017(8) C7B 0.0238(9) 0.0246(8) 0.0231(8) -0.0093(7) -0.0001(7) -0.0053(7) C8B 0.0249(9) 0.0211(8) 0.0239(8) -0.0091(7) -0.0014(7) -0.0037(7) C9B 0.0336(11) 0.0282(9) 0.0252(9) -0.0088(8) -0.0035(8) -0.0030(8) C10B 0.0531(15) 0.0384(12) 0.0288(10) -0.0088(9) 0.0083(10) -0.0129(11) C11B 0.0480(15) 0.0464(13) 0.0423(13) -0.0193(11) 0.0171(11) -0.0245(12) C12B 0.0303(11) 0.0494(13) 0.0456(13) -0.0255(11) 0.0041(9) -0.0159(10) C13B 0.0290(10) 0.0325(10) 0.0299(9) -0.0138(8) -0.0038(8) -0.0053(8) N1B 0.0258(9) 0.0301(9) 0.0389(10) -0.0191(8) -0.0008(7) -0.0023(7) O1B 0.0242(7) 0.0450(9) 0.0399(8) -0.0255(7) -0.0016(6) -0.0090(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Br1A C9A 1.920(2) . ? C1A C8A 1.536(3) . ? C1A C2A 1.552(3) . ? C1A C7A 1.552(2) . ? C1A C6A 1.562(3) . ? C2A C3A 1.530(3) . ? C2A H2A1 0.99 . ? C2A H2A2 0.99 . ? C3A C4A 1.521(4) . ? C3A H3A1 0.99 . ? C3A H3A2 0.99 . ? C4A C5A 1.521(5) . ? C4A H4A1 0.99 . ? C4A H4A2 0.99 . ? C5A C6A 1.535(3) . ? C5A H5A1 0.99 . ? C5A H5A2 0.99 . ? C6A H6A1 0.99 . ? C6A H6A2 0.99 . ? C7A O1A 1.241(2) . ? C7A N1A 1.337(2) . ? C8A C13A 1.403(3) . ? C8A C9A 1.404(3) . ? C9A C10A 1.394(3) . ? C10A C11A 1.380(4) . ? C10A H10A 0.95 . ? C11A C12A 1.374(4) . ? C11A H11A 0.95 . ? C12A C13A 1.399(3) . ? C12A H12A 0.95 . ? C13A H13A 0.95 . ? N1A H1As 0.88(3) . ? N1A H1Aa 0.86(3) . ? Br1B C9B 1.906(2) . ? C1B C7B 1.541(3) . ? C1B C8B 1.543(3) . ? C1B C6B 1.550(2) . ? C1B C2B 1.554(3) . ? C2B C3B 1.542(3) . ? C2B H2B1 0.99 . ? C2B H2B2 0.99 . ? C3B C4B 1.527(3) . ? C3B H3B1 0.99 . ? C3B H3B2 0.99 . ? C4B C5B 1.522(3) . ? C4B H4B1 0.99 . ? C4B H4B2 0.99 . ? C5B C6B 1.526(3) . ? C5B H5B1 0.99 . ? C5B H5B2 0.99 . ? C6B H6B1 0.99 . ? C6B H6B2 0.99 . ? C7B O1B 1.229(2) . ? C7B N1B 1.346(3) . ? C8B C13B 1.405(3) . ? C8B C9B 1.408(3) . ? C9B C10B 1.390(3) . ? C10B C11B 1.381(4) . ? C10B H10B 0.95 . ? C11B C12B 1.379(4) . ? C11B H11B 0.95 . ? C12B C13B 1.390(3) . ? C12B H12B 0.95 . ? C13B H13B 0.95 . ? N1B H1Bs 0.86(3) . ? N1B H1Ba 0.84(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 C8A C1A C2A 110.62(15) . . ? C8A C1A C7A 109.91(15) . . ? C2A C1A C7A 111.05(15) . . ? C8A C1A C6A 114.12(16) . . ? C2A C1A C6A 108.66(17) . . ? C7A C1A C6A 102.21(15) . . ? C3A C2A C1A 113.13(19) . . ? C3A C2A H2A1 109 . . ? C1A C2A H2A1 109 . . ? C3A C2A H2A2 109 . . ? C1A C2A H2A2 109 . . ? H2A1 C2A H2A2 107.8 . . ? C4A C3A C2A 111.0(2) . . ? C4A C3A H3A1 109.4 . . ? C2A C3A H3A1 109.4 . . ? C4A C3A H3A2 109.4 . . ? C2A C3A H3A2 109.4 . . ? H3A1 C3A H3A2 108 . . ? C3A C4A C5A 110.0(2) . . ? C3A C4A H4A1 109.7 . . ? C5A C4A H4A1 109.7 . . ? C3A C4A H4A2 109.7 . . ? C5A C4A H4A2 109.7 . . ? H4A1 C4A H4A2 108.2 . . ? C4A C5A C6A 112.3(2) . . ? C4A C5A H5A1 109.1 . . ? C6A C5A H5A1 109.1 . . ? C4A C5A H5A2 109.1 . . ? C6A C5A H5A2 109.1 . . ? H5A1 C5A H5A2 107.9 . . ? C5A C6A C1A 115.71(19) . . ? C5A C6A H6A1 108.4 . . ? C1A C6A H6A1 108.4 . . ? C5A C6A H6A2 108.4 . . ? C1A C6A H6A2 108.4 . . ? H6A1 C6A H6A2 107.4 . . ? O1A C7A N1A 122.29(17) . . ? O1A C7A C1A 121.53(17) . . ? N1A C7A C1A 116.02(16) . . ? C13A C8A C9A 114.63(19) . . ? C13A C8A C1A 121.74(18) . . ? C9A C8A C1A 123.63(18) . . ? C10A C9A C8A 123.5(2) . . ? C10A C9A Br1A 114.68(18) . . ? C8A C9A Br1A 121.72(16) . . ? C11A C10A C9A 119.4(2) . . ? C11A C10A H10A 120.3 . . ? C9A C10A H10A 120.3 . . ? C12A C11A C10A 119.5(2) . . ? C12A C11A H11A 120.2 . . ? C10A C11A H11A 120.2 . . ? C11A C12A C13A 120.4(2) . . ? C11A C12A H12A 119.8 . . ? C13A C12A H12A 119.8 . . ? C12A C13A C8A 122.5(2) . . ? C12A C13A H13A 118.8 . . ? C8A C13A H13A 118.8 . . ? C7A N1A H1As 122.6(17) . . ? C7A N1A H1Aa 118.9(18) . . ? H1As N1A H1Aa 117(2) . . ? C7B C1B C8B 110.56(14) . . ? C7B C1B C6B 106.55(15) . . ? C8B C1B C6B 111.16(15) . . ? C7B C1B C2B 111.24(15) . . ? C8B C1B C2B 109.71(15) . . ? C6B C1B C2B 107.56(15) . . ? C3B C2B C1B 115.08(16) . . ? C3B C2B H2B1 108.5 . . ? C1B C2B H2B1 108.5 . . ? C3B C2B H2B2 108.5 . . ? C1B C2B H2B2 108.5 . . ? H2B1 C2B H2B2 107.5 . . ? C4B C3B C2B 112.49(18) . . ? C4B C3B H3B1 109.1 . . ? C2B C3B H3B1 109.1 . . ? C4B C3B H3B2 109.1 . . ? C2B C3B H3B2 109.1 . . ? H3B1 C3B H3B2 107.8 . . ? C5B C4B C3B 110.44(18) . . ? C5B C4B H4B1 109.6 . . ? C3B C4B H4B1 109.6 . . ? C5B C4B H4B2 109.6 . . ? C3B C4B H4B2 109.6 . . ? H4B1 C4B H4B2 108.1 . . ? C4B C5B C6B 110.50(18) . . ? C4B C5B H5B1 109.5 . . ? C6B C5B H5B1 109.5 . . ? C4B C5B H5B2 109.5 . . ? C6B C5B H5B2 109.5 . . ? H5B1 C5B H5B2 108.1 . . ? C5B C6B C1B 112.51(17) . . ? C5B C6B H6B1 109.1 . . ? C1B C6B H6B1 109.1 . . ? C5B C6B H6B2 109.1 . . ? C1B C6B H6B2 109.1 . . ? H6B1 C6B H6B2 107.8 . . ? O1B C7B N1B 121.43(18) . . ? O1B C7B C1B 122.48(17) . . ? N1B C7B C1B 116.09(17) . . ? C13B C8B C9B 115.09(18) . . ? C13B C8B C1B 121.21(16) . . ? C9B C8B C1B 123.68(17) . . ? C10B C9B C8B 122.4(2) . . ? C10B C9B Br1B 114.66(16) . . ? C8B C9B Br1B 122.93(16) . . ? C11B C10B C9B 120.4(2) . . ? C11B C10B H10B 119.8 . . ? C9B C10B H10B 119.8 . . ? C12B C11B C10B 119.1(2) . . ? C12B C11B H11B 120.4 . . ? C10B C11B H11B 120.4 . . ? C11B C12B C13B 120.2(2) . . ? C11B C12B H12B 119.9 . . ? C13B C12B H12B 119.9 . . ? C12B C13B C8B 122.7(2) . . ? C12B C13B H13B 118.6 . . ? C8B C13B H13B 118.6 . . ? C7B N1B H1Bs 112.1(19) . . ? C7B N1B H1Ba 122(2) . . ? H1Bs N1B H1Ba 123(3) . . ? 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 C8A C1A C2A C3A -75.2(2) . . . . ? C7A C1A C2A C3A 162.51(17) . . . . ? C6A C1A C2A C3A 50.8(2) . . . . ? C1A C2A C3A C4A -59.3(3) . . . . ? C2A C3A C4A C5A 59.3(3) . . . . ? C3A C4A C5A C6A -54.5(3) . . . . ? C4A C5A C6A C1A 50.1(3) . . . . ? C8A C1A C6A C5A 77.2(2) . . . . ? C2A C1A C6A C5A -46.7(2) . . . . ? C7A C1A C6A C5A -164.18(19) . . . . ? C8A C1A C7A O1A -143.24(18) . . . . ? C2A C1A C7A O1A -20.5(2) . . . . ? C6A C1A C7A O1A 95.2(2) . . . . ? C8A C1A C7A N1A 41.3(2) . . . . ? C2A C1A C7A N1A 164.06(17) . . . . ? C6A C1A C7A N1A -80.2(2) . . . . ? C2A C1A C8A C13A 118.24(19) . . . . ? C7A C1A C8A C13A -118.78(19) . . . . ? C6A C1A C8A C13A -4.7(3) . . . . ? C2A C1A C8A C9A -62.9(2) . . . . ? C7A C1A C8A C9A 60.1(2) . . . . ? C6A C1A C8A C9A 174.23(18) . . . . ? C13A C8A C9A C10A -2.0(3) . . . . ? C1A C8A C9A C10A 179.00(19) . . . . ? C13A C8A C9A Br1A 174.76(14) . . . . ? C1A C8A C9A Br1A -4.2(3) . . . . ? C8A C9A C10A C11A 0.7(3) . . . . ? Br1A C9A C10A C11A -176.35(17) . . . . ? C9A C10A C11A C12A 1.1(3) . . . . ? C10A C11A C12A C13A -1.3(3) . . . . ? C11A C12A C13A C8A -0.2(3) . . . . ? C9A C8A C13A C12A 1.8(3) . . . . ? C1A C8A C13A C12A -179.21(18) . . . . ? C7B C1B C2B C3B 66.4(2) . . . . ? C8B C1B C2B C3B -170.99(16) . . . . ? C6B C1B C2B C3B -50.0(2) . . . . ? C1B C2B C3B C4B 50.2(2) . . . . ? C2B C3B C4B C5B -52.3(2) . . . . ? C3B C4B C5B C6B 58.0(2) . . . . ? C4B C5B C6B C1B -61.7(2) . . . . ? C7B C1B C6B C5B -63.9(2) . . . . ? C8B C1B C6B C5B 175.60(16) . . . . ? C2B C1B C6B C5B 55.5(2) . . . . ? C8B C1B C7B O1B -128.48(19) . . . . ? C6B C1B C7B O1B 110.6(2) . . . . ? C2B C1B C7B O1B -6.3(2) . . . . ? C8B C1B C7B N1B 52.3(2) . . . . ? C6B C1B C7B N1B -68.6(2) . . . . ? C2B C1B C7B N1B 174.46(16) . . . . ? C7B C1B C8B C13B -125.85(19) . . . . ? C6B C1B C8B C13B -7.7(2) . . . . ? C2B C1B C8B C13B 111.10(19) . . . . ? C7B C1B C8B C9B 56.1(2) . . . . ? C6B C1B C8B C9B 174.24(18) . . . . ? C2B C1B C8B C9B -66.9(2) . . . . ? C13B C8B C9B C10B -2.8(3) . . . . ? C1B C8B C9B C10B 175.30(19) . . . . ? C13B C8B C9B Br1B 175.85(15) . . . . ? C1B C8B C9B Br1B -6.0(3) . . . . ? C8B C9B C10B C11B 1.7(4) . . . . ? Br1B C9B C10B C11B -177.06(19) . . . . ? C9B C10B C11B C12B 0.7(4) . . . . ? C10B C11B C12B C13B -1.9(4) . . . . ? C11B C12B C13B C8B 0.6(4) . . . . ? C9B C8B C13B C12B 1.7(3) . . . . ? C1B C8B C13B C12B -176.51(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1A H1As O1A 0.88(3) 2.11(3) 2.981(2) 174(2) 2_656 N1A H1Aa O1B 0.86(3) 2.08(3) 2.874(2) 153(2) . N1B H1Ba O1A 0.84(3) 2.21(3) 2.959(3) 149(3) 1_655 ### END