#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2005211.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2005211 loop_ _publ_author_name 'Barrett, D. M. Y.' 'Kahwa, I. A.' 'Williams, D. J.' _publ_section_title ; Formylation versus Alkylation of Secondary Amines in DMF ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 2069 _journal_page_last 2071 _journal_volume 52 _journal_year 1996 _chemical_formula_sum 'C21 H17 N3 O5' _chemical_formula_weight 391.4 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_type_scat_source 'SHELXTL/PC (Sheldrick, 1991)' _cell_angle_alpha 90 _cell_angle_beta 102.63(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.062(4) _cell_length_b 12.046(2) _cell_length_c 11.697(2) _cell_measurement_reflns_used 18 _cell_measurement_temperature 291 _cell_measurement_theta_max 16.1 _cell_measurement_theta_min 3.2 _cell_volume 1933.4(7) _diffrn_measurement_device 'Siemens P4/RA' _diffrn_measurement_method '\w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 3187 _diffrn_reflns_theta_max 62 _diffrn_standards_decay_% insignificant _diffrn_standards_interval_count 100 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.815 _exptl_absorpt_correction_type none _exptl_crystal_colour brown _exptl_crystal_density_diffrn 1.345 _exptl_crystal_description plate _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.33 _refine_diff_density_max 0.21 _refine_diff_density_min -0.24 _refine_ls_extinction_coef '\c = 0.031(3)' _refine_ls_extinction_method 'F^*^ = F[1 + 0.002\cF^2^/sin(2\q)]^-1/4^' _refine_ls_goodness_of_fit_obs 2.47 _refine_ls_hydrogen_treatment noref _refine_ls_number_parameters 263 _refine_ls_number_reflns 2712 _refine_ls_R_factor_obs 0.0464 _refine_ls_shift/esd_max 0.026 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme ' 1/[\s^2^(F)+0.0005F^2^]' _refine_ls_wR_factor_obs 0.0539 _reflns_number_observed 2712 _reflns_number_total 3034 _reflns_observed_criterion F>4.0\s(F) _[local]_cod_data_source_file bk1124.cif _[local]_cod_data_source_block bk1124a _cod_database_code 2005211 loop_ _symmetry_equiv_pos_as_xyz x,y,z x,1/2-y,1/2+z -x,-y,-z -x,1/2+y,1/2-z loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv N(1) .64780(10) .73830(10) .10000(10) .0540(10) C(2) .60260(10) .6535(2) .0276(2) .0590(10) O(2) .61100(10) .55650(10) .0522(2) .0890(10) C(3) .54430(10) .7084(2) -.0787(2) .0560(10) C(4) .4861(2) .6645(2) -.1778(2) .0760(10) C(5) .4412(2) .7390(3) -.2637(2) .0880(10) C(6) .4547(2) .8517(3) -.2496(2) .0900(10) C(7) .5118(2) .8950(2) -.1484(2) .0750(10) C(8) .55730(10) .8217(2) -.0641(2) .0570(10) C(9) .62370(10) .8420(2) .0509(2) .0600(10) O(9) .65290(10) .92930(10) .0967(2) .0850(10) C(10) .71790(10) .7198(2) .2098(2) .0650(10) C(11) .81850(10) .6911(2) .1901(2) .0540(10) N(12) .85670(10) .77810(10) .12670(10) .0460(10) C(13) .89910(10) .87650(10) .1895(2) .0530(10) C(14) 1.00090(10) .8567(2) .2621(2) .0600(10) N(15) 1.06680(10) .81920(10) .18970(10) .0520(10) C(16) 1.11270(10) .89030(10) .1250(2) .0520(10) O(16) 1.10640(10) .98990(10) .12470(10) .0780(10) C(17) 1.16750(10) .81810(10) .0593(2) .0520(10) C(18) 1.2244(2) .8465(2) -.0184(2) .0700(10) C(19) 1.2659(2) .7603(3) -.0687(2) .0860(10) C(20) 1.2512(2) .6521(3) -.0427(2) .0910(10) C(21) 1.1938(2) .6227(2) .0355(2) .0770(10) C(22) 1.15260(10) .7089(2) .0865(2) .0570(10) C(23) 1.08740(10) .70800(10) .1715(2) .0570(10) O(23) 1.05690(10) .63050(10) .2176(2) .0820(10) C(24) .8583(2) .7631(2) .0137(2) .0580(10) O(24) .82840(10) .68120(10) -.04410(10) .0860(10) H(4A) .4764 .5859 -.1868 .091 H(5A) .4009 .7122 -.3354 .105 H(6A) .4232 .9013 -.3105 .108 H(7A) .5202 .9736 -.1365 .090 H(10A) .6948 .6610 .2521 .078 H(10B) .7232 .7858 .2567 .078 H(11A) .8630 .6784 .2638 .065 H(11B) .8136 .6236 .1455 .065 H(13A) .8572 .9025 .2385 .064 H(13B) .9031 .9337 .1336 .064 H(14A) 1.0258 .9234 .3028 .072 H(14B) .9973 .8006 .3192 .072 H(18A) 1.2343 .9229 -.0360 .085 H(19A) 1.3066 .7766 -.1227 .103 H(20A) 1.2801 .5939 -.0797 .109 H(21A) 1.1826 .5472 .0552 .091 H(24A) .8852 .8214 -.0253 .071 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C(2) N(1) C(9) 111.90(10) yes C(9) N(1) C(10) 124.2(2) yes N(1) C(2) C(3) 106.10(10) yes C(2) C(3) C(4) 130.8(2) yes C(4) C(3) C(8) 121.6(2) yes C(4) C(5) C(6) 121.4(2) yes C(6) C(7) C(8) 117.7(2) yes C(3) C(8) C(9) 108.4(2) yes N(1) C(9) C(8) 106.10(10) yes C(8) C(9) O(9) 129.1(2) yes C(10) C(11) N(12) 111.9(2) yes C(11) N(12) C(24) 119.60(10) yes N(12) C(13) C(14) 112.90(10) yes C(14) N(15) C(16) 123.70(10) yes C(16) N(15) C(23) 111.7(2) yes N(15) C(16) C(17) 106.10(10) yes C(16) C(17) C(18) 129.7(2) yes C(18) C(17) C(22) 121.8(2) yes C(18) C(19) C(20) 121.5(3) yes C(20) C(21) C(22) 116.7(2) yes C(17) C(22) C(23) 107.9(2) yes N(15) C(23) C(22) 105.8(2) yes C(22) C(23) O(23) 129.4(2) yes C(2) N(1) C(10) 123.8(2) yes N(1) C(2) O(2) 124.1(2) yes O(2) C(2) C(3) 129.8(2) yes C(2) C(3) C(8) 107.60(10) yes C(3) C(4) C(5) 117.0(2) yes C(5) C(6) C(7) 121.0(2) yes C(3) C(8) C(7) 121.2(2) yes C(7) C(8) C(9) 130.4(2) yes N(1) C(9) O(9) 124.8(2) yes N(1) C(10) C(11) 111.9(2) yes C(11) N(12) C(13) 119.20(10) yes C(13) N(12) C(24) 121.1(2) yes C(13) C(14) N(15) 111.50(10) yes C(14) N(15) C(23) 124.5(2) yes N(15) C(16) O(16) 125.0(2) yes O(16) C(16) C(17) 128.9(2) yes C(16) C(17) C(22) 108.5(2) yes C(17) C(18) C(19) 117.0(2) yes C(19) C(20) C(21) 121.9(3) yes C(17) C(22) C(21) 121.0(2) yes C(21) C(22) C(23) 131.1(2) yes N(15) C(23) O(23) 124.7(2) yes N(12) C(24) O(24) 125.5(2) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N(1) C(2) 1.390(2) yes N(1) C(10) 1.455(2) yes C(2) C(3) 1.487(3) yes C(3) C(8) 1.382(3) yes C(5) C(6) 1.376(5) yes C(7) C(8) 1.373(3) yes C(9) O(9) 1.210(2) yes C(11) N(12) 1.453(2) yes N(12) C(24) 1.339(2) yes C(14) N(15) 1.456(3) yes N(15) C(23) 1.397(2) yes C(16) C(17) 1.483(3) yes C(17) C(22) 1.380(3) yes C(19) C(20) 1.364(4) yes C(21) C(22) 1.386(3) yes C(23) O(23) 1.203(3) yes N(1) C(9) 1.385(2) yes C(2) O(2) 1.203(2) yes C(3) C(4) 1.370(3) yes C(4) C(5) 1.390(4) yes C(6) C(7) 1.379(3) yes C(8) C(9) 1.481(3) yes C(10) C(11) 1.523(3) yes N(12) C(13) 1.452(2) yes C(13) C(14) 1.515(2) yes N(15) C(16) 1.391(2) yes C(16) O(16) 1.203(2) yes C(17) C(18) 1.379(3) yes C(18) C(19) 1.383(4) yes C(20) C(21) 1.392(4) yes C(22) C(23) 1.492(3) yes C(24) O(24) 1.218(2) yes