#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/41/2204194.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_2204194 loop_ _publ_author_name 'Efr\'en V. Garc\'ia-B\'aez' 'Beatriz A. L\'opez-Romero' 'Francisco J. Mart\'inez-Mart\'inez' 'Herbert H\"opfl' 'Itzia I. Padilla-Mart\'inez' _publ_section_title ; Dimethyl N,N'-(1,2-phenylene)dicarbamate ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1488 _journal_page_last o1490 _journal_paper_doi 10.1107/S1600536804018690 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C10 H12 N2 O4' _chemical_formula_moiety 'C10 H12 N2 O4' _chemical_formula_sum 'C10 H12 N2 O4' _chemical_formula_weight 224.22 _chemical_name_systematic ; Dimethyl N,N'-(1,2-phenylene)dicarbamate ; _space_group_IT_number 7 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P -2yac' _symmetry_space_group_name_H-M 'P 1 n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 100.181(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 9.3056(19) _cell_length_b 4.8400(10) _cell_length_c 11.843(2) _cell_measurement_reflns_used 600 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25 _cell_measurement_theta_min 20 _cell_volume 525.00(18) _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_collection 'SMART (Bruker, 2000)' _computing_data_reduction 'SAINT ' _computing_molecular_graphics 'SHELXTL (Bruker, 2000)' _computing_publication_material 'SHELXL97 and WinGX2003 (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS (Sheldrick, 1997)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device 'Bruker SMART Area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 4221 _diffrn_reflns_theta_full 27.51 _diffrn_reflns_theta_max 27.51 _diffrn_reflns_theta_min 2.57 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 236 _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.36 _refine_diff_density_max 0.253 _refine_diff_density_min -0.243 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 145 _refine_ls_number_reflns 1203 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.096 _refine_ls_R_factor_all 0.0316 _refine_ls_R_factor_gt 0.0307 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0548P)^2^+0.0358P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0804 _refine_ls_wR_factor_ref 0.0811 _reflns_number_gt 1168 _reflns_number_total 1203 _reflns_threshold_expression I>2\s(I) _cod_data_source_file lh6247.cif _cod_data_source_block I _cod_original_cell_volume 525.00(19) _cod_original_sg_symbol_H-M 'P n' _cod_database_code 2204194 _cod_database_fobs_code 2204194 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2+x,-y,1/2+z loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O8 0.0206(7) 0.0162(6) 0.0251(7) 0.0026(5) 0.0026(5) -0.0001(5) O9 0.0185(7) 0.0199(6) 0.0235(7) 0.0020(5) 0.0018(5) -0.0030(5) O12 0.0221(7) 0.0304(7) 0.0280(7) 0.0063(6) 0.0083(5) 0.0053(6) O13 0.0240(7) 0.0294(8) 0.0215(7) 0.0052(6) 0.0065(5) 0.0090(6) N7 0.0183(8) 0.0139(7) 0.0238(8) 0.0013(6) 0.0051(6) 0.0004(6) N11 0.0162(7) 0.0247(8) 0.0213(7) 0.0028(6) 0.0053(5) 0.0057(6) C1 0.0199(9) 0.0168(8) 0.0170(8) -0.0001(7) 0.0023(6) -0.0027(7) C2 0.0199(9) 0.0195(8) 0.0178(8) 0.0004(7) 0.0027(6) 0.0006(7) C3 0.0191(9) 0.0305(10) 0.0287(10) -0.0010(8) 0.0008(7) 0.0080(8) C4 0.0232(10) 0.0339(12) 0.0297(10) 0.0012(9) -0.0055(8) 0.0080(9) C5 0.0315(11) 0.0275(10) 0.0203(9) -0.0004(8) -0.0036(7) 0.0077(8) C6 0.0245(9) 0.0201(9) 0.0212(9) -0.0041(7) 0.0035(7) 0.0010(7) C8 0.0185(9) 0.0200(9) 0.0138(8) 0.0007(7) 0.0056(6) 0.0021(6) C10 0.0174(9) 0.0247(10) 0.0313(11) -0.0013(7) -0.0009(7) -0.0043(8) C12 0.0180(9) 0.0201(9) 0.0179(8) -0.0022(7) 0.0016(6) -0.0008(7) C14 0.0273(10) 0.0337(10) 0.0204(9) 0.0010(9) 0.0062(7) 0.0061(8) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_type_symbol O8 -0.19061(14) 0.1083(3) 0.10711(12) 0.0208(4) Uani 1.000 O O9 -0.35873(14) 0.4484(3) 0.09391(12) 0.0209(4) Uani 1.000 O O12 0.27835(16) 0.8008(3) -0.01981(13) 0.0264(4) Uani 1.000 O O13 0.09521(15) 1.1075(3) -0.06882(12) 0.0247(4) Uani 1.000 O N7 -0.12992(17) 0.5497(3) 0.16398(13) 0.0185(4) Uani 1.000 N N11 0.08810(17) 0.8377(3) 0.07911(14) 0.0205(4) Uani 1.000 N C1 0.0202(2) 0.4979(4) 0.20952(15) 0.0180(5) Uani 1.000 C C2 0.1292(2) 0.6385(4) 0.16561(16) 0.0191(5) Uani 1.000 C C3 0.2751(2) 0.5854(4) 0.21131(19) 0.0265(6) Uani 1.000 C C4 0.3108(2) 0.3919(5) 0.2986(2) 0.0302(6) Uani 1.000 C C5 0.2023(3) 0.2534(5) 0.34212(18) 0.0274(6) Uani 1.000 C C6 0.0572(2) 0.3093(4) 0.29873(16) 0.0220(5) Uani 1.000 C C8 -0.22298(19) 0.3497(4) 0.12072(14) 0.0171(5) Uani 1.000 C C10 -0.4680(2) 0.2582(4) 0.03770(18) 0.0251(6) Uani 1.000 C C12 0.1666(2) 0.9051(4) -0.00369(15) 0.0189(5) Uani 1.000 C C14 0.1645(2) 1.1978(5) -0.16184(17) 0.0269(6) Uani 1.000 C H3 0.34861 0.67944 0.18342 0.0318 Uiso 1.000 H H4 0.40834 0.35526 0.32795 0.0362 Uiso 1.000 H H5 0.22683 0.12353 0.40020 0.0329 Uiso 1.000 H H6 -0.01593 0.22064 0.32928 0.0264 Uiso 1.000 H H7 -0.16190 0.71632 0.16437 0.0222 Uiso 1.000 H H10A -0.56115 0.34899 0.02257 0.0377 Uiso 1.000 H H10B -0.47330 0.10144 0.08646 0.0377 Uiso 1.000 H H10C -0.44221 0.19776 -0.03330 0.0377 Uiso 1.000 H H11 0.00703 0.92341 0.07857 0.0246 Uiso 1.000 H H14A 0.10743 1.34220 -0.20354 0.0404 Uiso 1.000 H H14B 0.17174 1.04517 -0.21230 0.0404 Uiso 1.000 H H14C 0.26042 1.26619 -0.13172 0.0404 Uiso 1.000 H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C8 O9 C10 116.17(15) no C12 O13 C14 114.63(15) no C1 N7 C8 122.75(15) no C2 N11 C12 125.17(16) no C1 N7 H7 118.62 no C8 N7 H7 118.62 no C2 N11 H11 117.41 no C12 N11 H11 117.42 no N7 C1 C2 120.03(16) no N7 C1 C6 119.72(16) no C2 C1 C6 120.24(17) no C1 C2 C3 119.18(18) no N11 C2 C1 118.85(17) no N11 C2 C3 121.93(17) no C2 C3 C4 120.07(18) no C3 C4 C5 120.56(19) no C4 C5 C6 119.7(2) no C1 C6 C5 120.27(18) no O8 C8 O9 123.68(17) yes O8 C8 N7 125.65(17) yes O9 C8 N7 110.67(16) yes O12 C12 N11 127.11(18) yes O13 C12 N11 108.27(16) yes O12 C12 O13 124.59(17) yes C2 C3 H3 119.95 no C4 C3 H3 119.98 no C3 C4 H4 119.69 no C5 C4 H4 119.75 no C4 C5 H5 120.17 no C6 C5 H5 120.17 no C1 C6 H6 119.85 no C5 C6 H6 119.89 no O9 C10 H10A 109.46 no O9 C10 H10B 109.47 no O9 C10 H10C 109.47 no H10A C10 H10B 109.47 no H10A C10 H10C 109.47 no H10B C10 H10C 109.48 no O13 C14 H14A 109.44 no O13 C14 H14B 109.45 no O13 C14 H14C 109.47 no H14A C14 H14B 109.47 no H14A C14 H14C 109.49 no H14B C14 H14C 109.50 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O8 C8 1.224(2) yes O9 C8 1.335(2) yes O9 C10 1.444(2) yes O12 C12 1.201(2) yes O13 C12 1.347(2) yes O13 C14 1.439(2) yes N7 C1 1.428(2) yes N7 C8 1.339(2) yes N11 C2 1.410(2) yes N11 C12 1.362(2) yes N7 H7 0.8599 no N11 H11 0.8600 no C1 C6 1.393(3) no C1 C2 1.396(3) no C2 C3 1.394(3) no C3 C4 1.391(3) no C4 C5 1.385(3) no C5 C6 1.384(3) no C3 H3 0.9296 no C4 H4 0.9298 no C5 H5 0.9300 no C6 H6 0.9302 no C10 H10A 0.9600 no C10 H10B 0.9600 no C10 H10C 0.9600 no C14 H14A 0.9600 no C14 H14B 0.9600 no C14 H14C 0.9597 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag O8 N7 2.819(2) 1_545 no O8 N11 2.976(2) 1_545 no O8 C6 3.093(2) . no O9 C14 3.335(3) 2_475 no O12 C3 2.934(3) . no O12 C10 3.220(3) 1_665 no O8 H7 2.0166 1_545 no O8 H11 2.1254 1_545 no O8 H5 2.6811 2_454 no O8 H14B 2.7812 2_465 no O8 H6 2.8894 . no O8 H10B 2.5988 . no O8 H10C 2.6567 . no O9 H14A 2.6735 2_475 no O12 H3 2.4514 . no O12 H10A 2.6457 1_655 no O12 H10B 2.8309 1_665 no O12 H14B 2.6039 . no O12 H14C 2.8985 1_545 no O12 H14C 2.6038 . no O12 H6 2.8424 2_564 no N7 O8 2.819(2) 1_565 no N7 N11 2.791(2) . no N7 C14 3.287(3) 2_475 no N11 O8 2.976(2) 1_565 no N11 N7 2.791(2) . no N7 H14C 2.9261 2_475 no N7 H11 2.5248 . no N11 H7 2.7581 . no C3 O12 2.934(3) . no C6 O8 3.093(2) . no C6 C10 3.561(3) 2_565 no C10 O12 3.220(3) 1_445 no C10 C6 3.561(3) 2_464 no C14 O9 3.335(3) 2_574 no C14 N7 3.287(3) 2_574 no C3 H14A 3.0985 2_575 no C4 H14A 3.0498 2_575 no C5 H10C 3.0749 2_555 no C8 H6 2.9191 . no C8 H14B 3.0345 2_465 no C8 H11 3.0765 1_545 no C10 H14C 2.9362 1_445 no C12 H3 2.7650 . no C14 H7 2.8625 2_574 no H3 O12 2.4514 . no H3 C12 2.7650 . no H3 H14A 2.5425 2_575 no H4 H14A 2.4413 2_575 no H5 O8 2.6811 2_555 no H5 H10C 2.4394 2_555 no H6 O8 2.8894 . no H6 C8 2.9191 . no H6 O12 2.8424 2_465 no H7 O8 2.0166 1_565 no H7 N11 2.7581 . no H7 H11 2.2523 . no H7 C14 2.8625 2_475 no H7 H14B 2.5811 2_475 no H10A O12 2.6457 1_455 no H10A H14C 2.2768 1_445 no H10B O8 2.5988 . no H10B O12 2.8309 1_445 no H10C O8 2.6567 . no H10C C5 3.0749 2_454 no H10C H5 2.4394 2_454 no H11 O8 2.1254 1_565 no H11 N7 2.5248 . no H11 C8 3.0765 1_565 no H11 H7 2.2523 . no H14A O9 2.6735 2_574 no H14A C3 3.0985 2_474 no H14A C4 3.0498 2_474 no H14A H3 2.5425 2_474 no H14A H4 2.4413 2_474 no H14B O12 2.6039 . no H14B O8 2.7812 2_564 no H14B C8 3.0345 2_564 no H14B H7 2.5811 2_574 no H14C O12 2.6038 . no H14C O12 2.8985 1_565 no H14C C10 2.9362 1_665 no H14C H10A 2.2768 1_665 no H14C N7 2.9261 2_574 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N7 H7 O8 1_565 0.86 2.02 2.819(2) 155 yes N11 H11 O8 1_565 0.86 2.13 2.976(2) 170 yes C3 H3 O12 . 0.93 2.45 2.934(3) 112 no 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_publ_flag C10 O9 C8 O8 -5.0(3) no C10 O9 C8 N7 175.17(15) yes C14 O13 C12 O12 -0.8(3) no C14 O13 C12 N11 -179.04(16) yes C1 N7 C8 O9 174.24(15) no C8 N7 C1 C2 123.6(2) no C8 N7 C1 C6 -57.2(2) yes C1 N7 C8 O8 -5.6(3) no C12 N11 C2 C3 31.7(3) yes C2 N11 C12 O12 3.4(3) no C12 N11 C2 C1 -150.73(18) no C2 N11 C12 O13 -178.46(16) no C6 C1 C2 N11 -176.99(17) no N7 C1 C2 N11 2.2(3) no N7 C1 C2 C3 179.91(17) no C2 C1 C6 C5 -2.0(3) no C6 C1 C2 C3 0.7(3) no N7 C1 C6 C5 178.76(18) no N11 C2 C3 C4 178.40(19) no C1 C2 C3 C4 0.8(3) no C2 C3 C4 C5 -1.0(3) no C3 C4 C5 C6 -0.3(3) no C4 C5 C6 C1 1.8(3) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 224386 2 PubChem 255880