#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/56/2225667.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_2225667
loop_
_publ_author_name
'Meskini, Ihssan'
'Daoudi, Maria'
'Daran, Jean-Claude'
'Zouihri, Hafid'
'Ben Hadda, Taibi'
_publ_section_title
;
 Diethyl
 2-[(N-benzyl-N-methylamino)(phenyl)methyl]propanedioate
;
_journal_coeditor_code           PV2262
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o746
_journal_paper_doi               10.1107/S1600536810007506
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C22 H27 N O4'
_chemical_formula_moiety         'C22 H27 N O4'
_chemical_formula_sum            'C22 H27 N O4'
_chemical_formula_weight         369.45
_chemical_melting_point_gt       380
_chemical_melting_point_lt       382
_chemical_name_systematic
;
Diethyl 2-[(N-benzyl-N-methylamino)(phenyl)methyl]propanedioate
;
_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_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                 92.9990(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3074(2)
_cell_length_b                   5.90770(10)
_cell_length_c                   37.0971(7)
_cell_measurement_pressure       101
_cell_measurement_reflns_used    3214
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      1.9
_cell_volume                     2037.00(7)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker X8 APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            25575
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.10
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.258
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.252
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4138
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.253
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0695
_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/[σ²(Fo²)+(0.0364P)²+1.9835P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1586
_reflns_number_gt                3411
_reflns_number_total             4138
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2262.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225667
_cod_database_fobs_code          2225667
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'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4969(3) 0.3979(4) 0.18855(6) 0.0302(5) Uani d . 1 . .
H H1A 0.5442 0.5408 0.1841 0.036 Uiso calc R 1 . .
H H1B 0.5646 0.3016 0.2021 0.036 Uiso calc R 1 . .
C C2 0.5612(3) 0.3238(4) 0.12647(6) 0.0290(5) Uani d . 1 . .
H H2 0.5900 0.4832 0.1279 0.035 Uiso calc R 1 . .
C C3 0.4123(3) 0.0546(4) 0.15968(7) 0.0391(6) Uani d . 1 . .
H H3A 0.3777 -0.0094 0.1371 0.059 Uiso calc R 1 . .
H H3B 0.3374 0.0494 0.1765 0.059 Uiso calc R 1 . .
H H3C 0.4938 -0.0305 0.1691 0.059 Uiso calc R 1 . .
C C4 0.4827(3) 0.2917(4) 0.08947(6) 0.0318(6) Uani d . 1 . .
H H4 0.4493 0.1349 0.0870 0.038 Uiso calc R 1 . .
C C5 0.5794(3) 0.3490(5) 0.05896(6) 0.0354(6) Uani d . 1 . .
C C6 0.3536(3) 0.4517(5) 0.08739(6) 0.0402(7) Uani d . 1 . .
C C11 0.3667(3) 0.4396(4) 0.21050(6) 0.0277(5) Uani d . 1 . .
C C12 0.3634(3) 0.3693(5) 0.24598(7) 0.0379(6) Uani d . 1 . .
H H12 0.4411 0.2903 0.2565 0.045 Uiso calc R 1 . .
C C13 0.2448(3) 0.4158(5) 0.26603(7) 0.0453(7) Uani d . 1 . .
H H13 0.2434 0.3673 0.2899 0.054 Uiso calc R 1 . .
C C14 0.1298(3) 0.5327(5) 0.25081(7) 0.0404(7) Uani d . 1 . .
H H14 0.0509 0.5649 0.2643 0.048 Uiso calc R 1 . .
C C15 0.1318(3) 0.6024(5) 0.21538(7) 0.0388(6) Uani d . 1 . .
H H15 0.0536 0.6805 0.2049 0.047 Uiso calc R 1 . .
C C16 0.2495(3) 0.5565(4) 0.19540(6) 0.0328(6) Uani d . 1 . .
H H16 0.2500 0.6046 0.1715 0.039 Uiso calc R 1 . .
C C21 0.6990(3) 0.1854(4) 0.13072(6) 0.0274(5) Uani d . 1 . .
C C22 0.7136(3) -0.0263(4) 0.11485(6) 0.0306(5) Uani d . 1 . .
H H22 0.6362 -0.0897 0.1015 0.037 Uiso calc R 1 . .
C C23 0.8421(3) -0.1431(5) 0.11870(7) 0.0380(6) Uani d . 1 . .
H H23 0.8507 -0.2839 0.1078 0.046 Uiso calc R 1 . .
C C24 0.9581(3) -0.0524(5) 0.13858(7) 0.0396(6) Uani d . 1 . .
H H24 1.0448 -0.1308 0.1408 0.048 Uiso calc R 1 . .
C C25 0.9443(3) 0.1542(5) 0.15501(7) 0.0403(7) Uani d . 1 . .
H H25 1.0213 0.2151 0.1688 0.048 Uiso calc R 1 . .
C C26 0.8162(3) 0.2716(5) 0.15109(6) 0.0352(6) Uani d . 1 . .
H H26 0.8082 0.4115 0.1623 0.042 Uiso calc R 1 . .
C C31 0.0998(4) 0.4617(8) 0.07836(10) 0.0745(12) Uani d D 1 . .
H H31A 0.0644 0.4759 0.1024 0.089 Uiso calc PR 0.53 A 1
H H31B 0.1156 0.6124 0.0690 0.089 Uiso calc PR 0.53 A 1
H H31C 0.0277 0.3731 0.0900 0.089 Uiso d PR 0.47 A 2
H H31D 0.1145 0.5999 0.0922 0.089 Uiso d PR 0.47 A 2
C C32 0.0021(6) 0.3502(13) 0.05651(16) 0.0556(17) Uani d PD 0.53 B 1
H H32A -0.0853 0.4364 0.0542 0.083 Uiso calc PR 0.53 B 1
H H32B -0.0173 0.2047 0.0667 0.083 Uiso calc PR 0.53 B 1
H H32C 0.0398 0.3305 0.0331 0.083 Uiso calc PR 0.53 B 1
C C32B 0.0454(7) 0.5197(15) 0.04332(18) 0.059(2) Uani d PD 0.47 B 2
H H32D 0.0514 0.3908 0.0277 0.088 Uiso calc PR 0.47 B 2
H H32E 0.1010 0.6418 0.0342 0.088 Uiso calc PR 0.47 B 2
H H32F -0.0533 0.5659 0.0443 0.088 Uiso calc PR 0.47 B 2
C C41 0.6429(4) 0.2245(6) 0.00078(8) 0.0617(10) Uani d . 1 . .
H H41A 0.6915 0.3698 0.0009 0.074 Uiso calc R 1 . .
H H41B 0.5837 0.2120 -0.0214 0.074 Uiso calc R 1 . .
C C42 0.7512(5) 0.0371(8) 0.00302(11) 0.0870(13) Uani d . 1 . .
H H42A 0.8178 0.0623 0.0233 0.131 Uiso calc R 1 . .
H H42B 0.8025 0.0334 -0.0188 0.131 Uiso calc R 1 . .
H H42C 0.7029 -0.1047 0.0060 0.131 Uiso calc R 1 . .
N N1 0.4551(2) 0.2901(3) 0.15416(5) 0.0284(5) Uani d . 1 . .
O O1 0.3600(3) 0.6519(4) 0.09128(6) 0.0592(6) Uani d . 1 . .
O O2 0.2341(2) 0.3345(4) 0.07988(5) 0.0529(6) Uani d . 1 B .
O O3 0.6643(3) 0.5002(4) 0.05932(5) 0.0576(6) Uani d . 1 . .
O O4 0.5537(2) 0.2080(4) 0.03170(5) 0.0509(6) Uani d . 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C11 . . 110.89(19) ?
N1 C1 H1A . . 109.5 ?
C11 C1 H1A . . 109.5 ?
N1 C1 H1B . . 109.5 ?
C11 C1 H1B . . 109.5 ?
H1A C1 H1B . . 108.0 ?
N1 C2 C21 . . 116.50(19) ?
N1 C2 C4 . . 107.57(19) ?
C21 C2 C4 . . 112.69(19) ?
N1 C2 H2 . . 106.5 ?
C21 C2 H2 . . 106.5 ?
C4 C2 H2 . . 106.5 ?
N1 C3 H3A . . 109.5 ?
N1 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
N1 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
C5 C4 C6 . . 108.6(2) ?
C5 C4 C2 . . 111.5(2) ?
C6 C4 C2 . . 107.79(19) ?
C5 C4 H4 . . 109.6 ?
C6 C4 H4 . . 109.6 ?
C2 C4 H4 . . 109.6 ?
O3 C5 O4 . . 125.0(2) ?
O3 C5 C4 . . 125.2(2) ?
O4 C5 C4 . . 109.8(2) ?
O1 C6 O2 . . 125.4(3) ?
O1 C6 C4 . . 125.0(3) ?
O2 C6 C4 . . 109.6(2) ?
C12 C11 C16 . . 118.6(2) ?
C12 C11 C1 . . 121.4(2) ?
C16 C11 C1 . . 119.9(2) ?
C11 C12 C13 . . 120.6(2) ?
C11 C12 H12 . . 119.7 ?
C13 C12 H12 . . 119.7 ?
C14 C13 C12 . . 120.2(2) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C13 C14 C15 . . 119.6(2) ?
C13 C14 H14 . . 120.2 ?
C15 C14 H14 . . 120.2 ?
C14 C15 C16 . . 120.3(3) ?
C14 C15 H15 . . 119.9 ?
C16 C15 H15 . . 119.9 ?
C15 C16 C11 . . 120.7(2) ?
C15 C16 H16 . . 119.6 ?
C11 C16 H16 . . 119.6 ?
C26 C21 C22 . . 117.9(2) ?
C26 C21 C2 . . 119.5(2) ?
C22 C21 C2 . . 122.6(2) ?
C23 C22 C21 . . 120.5(2) ?
C23 C22 H22 . . 119.7 ?
C21 C22 H22 . . 119.7 ?
C22 C23 C24 . . 120.6(3) ?
C22 C23 H23 . . 119.7 ?
C24 C23 H23 . . 119.7 ?
C25 C24 C23 . . 119.5(3) ?
C25 C24 H24 . . 120.2 ?
C23 C24 H24 . . 120.2 ?
C24 C25 C26 . . 120.0(2) ?
C24 C25 H25 . . 120.0 ?
C26 C25 H25 . . 120.0 ?
C25 C26 C21 . . 121.5(2) ?
C25 C26 H26 . . 119.3 ?
C21 C26 H26 . . 119.3 ?
C32 C31 C32B . . 51.0(4) ?
C32 C31 O2 . . 108.7(4) ?
C32B C31 O2 . . 115.3(4) ?
C32 C31 H31A . . 110.0 ?
C32B C31 H31A . . 134.6 ?
O2 C31 H31A . . 110.0 ?
C32 C31 H31B . . 110.0 ?
C32B C31 H31B . . 60.1 ?
O2 C31 H31B . . 110.0 ?
H31A C31 H31B . . 108.3 ?
C32 C31 H31C . . 63.0 ?
C32B C31 H31C . . 108.5 ?
O2 C31 H31C . . 108.5 ?
H31A C31 H31C . . 50.3 ?
H31B C31 H31C . . 140.9 ?
C32 C31 H31D . . 142.7 ?
C32B C31 H31D . . 108.4 ?
O2 C31 H31D . . 108.5 ?
H31A C31 H31D . . 59.1 ?
H31B C31 H31D . . 52.9 ?
H31C C31 H31D . . 107.5 ?
C31 C32 H31C . . 43.3 ?
C31 C32 H32A . . 109.5 ?
H31C C32 H32A . . 98.3 ?
C31 C32 H32B . . 109.5 ?
H31C C32 H32B . . 74.8 ?
C31 C32 H32C . . 109.5 ?
H31C C32 H32C . . 147.7 ?
C31 C32B H32D . . 109.5 ?
C31 C32B H32E . . 109.5 ?
H32D C32B H32E . . 109.5 ?
C31 C32B H32F . . 109.5 ?
H32D C32B H32F . . 109.5 ?
H32E C32B H32F . . 109.5 ?
O4 C41 C42 . . 108.5(3) ?
O4 C41 H41A . . 110.0 ?
C42 C41 H41A . . 110.0 ?
O4 C41 H41B . . 110.0 ?
C42 C41 H41B . . 110.0 ?
H41A C41 H41B . . 108.4 ?
C41 C42 H42A . . 109.5 ?
C41 C42 H42B . . 109.5 ?
H42A C42 H42B . . 109.5 ?
C41 C42 H42C . . 109.5 ?
H42A C42 H42C . . 109.5 ?
H42B C42 H42C . . 109.5 ?
C1 N1 C3 . . 110.74(19) ?
C1 N1 C2 . . 113.09(19) ?
C3 N1 C2 . . 114.98(19) ?
C6 O2 C31 . . 116.5(3) ?
C5 O4 C41 . . 118.2(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.460(3) ?
C1 C11 . 1.515(3) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 N1 . 1.475(3) ?
C2 C21 . 1.522(3) ?
C2 C4 . 1.533(3) ?
C2 H2 . 0.9800 ?
C3 N1 . 1.464(3) ?
C3 H3A . 0.9600 ?
C3 H3B . 0.9600 ?
C3 H3C . 0.9600 ?
C4 C5 . 1.521(4) ?
C4 C6 . 1.528(4) ?
C4 H4 . 0.9800 ?
C5 O3 . 1.192(3) ?
C5 O4 . 1.323(3) ?
C6 O1 . 1.192(3) ?
C6 O2 . 1.327(4) ?
C11 C12 . 1.382(3) ?
C11 C16 . 1.385(3) ?
C12 C13 . 1.390(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.370(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.378(4) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.381(4) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C21 C26 . 1.392(3) ?
C21 C22 . 1.392(3) ?
C22 C23 . 1.382(3) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.383(4) ?
C23 H23 . 0.9300 ?
C24 C25 . 1.373(4) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.380(4) ?
C25 H25 . 0.9300 ?
C26 H26 . 0.9300 ?
C31 C32 . 1.357(6) ?
C31 C32B . 1.412(7) ?
C31 O2 . 1.457(4) ?
C31 H31A . 0.9700 ?
C31 H31B . 0.9700 ?
C31 H31C . 0.9700 ?
C31 H31D . 0.9700 ?
C32 H31C . 1.2600 ?
C32 H32A . 0.9600 ?
C32 H32B . 0.9600 ?
C32 H32C . 0.9600 ?
C32B H32D . 0.9600 ?
C32B H32E . 0.9600 ?
C32B H32F . 0.9600 ?
C41 O4 . 1.454(3) ?
C41 C42 . 1.497(5) ?
C41 H41A . 0.9700 ?
C41 H41B . 0.9700 ?
C42 H42A . 0.9600 ?
C42 H42B . 0.9600 ?
C42 H42C . 0.9600 ?
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
C32 H32A O3 1_455 0.96 2.38 3.273(3) 155
