#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/44/2214499.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_2214499
loop_
_publ_author_name
'Boulcina, Raouf'
'Bouacida, Sofiane'
'Roisnel, Thierry'
'Debache, Abdelmadjid'
_publ_section_title
;
 Diethyl
 4-(4-bromophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
;
_journal_coeditor_code           AT2352
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3635
_journal_page_last               o3636
_journal_paper_doi               10.1107/S160053680703646X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C19 H22 Br N O4'
_chemical_formula_moiety         'C19 H22 Br N O4'
_chemical_formula_structural     'C19 H22 Br N O4'
_chemical_formula_sum            'C19 H22 Br N O4'
_chemical_formula_weight         408.28
_chemical_name_systematic
;
Diethyl 4-(4-bromophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 98.126(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0597(5)
_cell_length_b                   7.4244(4)
_cell_length_c                   24.3726(13)
_cell_measurement_reflns_used    8206
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.32
_cell_volume                     1802.05(16)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'APEX2 (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt,
2001)
;
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2002 (Burla et al.,  2003)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method
'CCD rotation images, thin slices, φ scans, and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            19743
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    2.304
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.332
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4132
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0270
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0459P)²+0.9623P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0933
_reflns_number_gt                3460
_reflns_number_total             4132
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2352.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2214499
_cod_database_fobs_code          2214499
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_thermal_displace_type
_atom_site_occupancy
Br Br 0.53359(2) 0.25548(3) 0.271070(10) 0.02310(10) Uani 1.000
O O1 1.15604(14) -0.0716(2) 0.14212(6) 0.0248(5) Uani 1.000
O O2 1.07916(15) 0.2138(2) 0.13729(6) 0.0213(4) Uani 1.000
O O3 0.72372(13) 0.42820(18) 0.00338(6) 0.0180(4) Uani 1.000
O O4 0.57284(14) 0.24035(17) -0.04326(6) 0.0181(4) Uani 1.000
N N1 0.81110(17) -0.1926(2) 0.02334(7) 0.0158(4) Uani 1.000
C C1 1.0102(2) -0.3304(3) 0.07312(9) 0.0204(6) Uani 1.000
C C2 0.92482(18) -0.1649(3) 0.06168(8) 0.0151(5) Uani 1.000
C C3 0.95008(18) 0.0016(3) 0.08344(8) 0.0138(5) Uani 1.000
C C4 0.84771(18) 0.1524(3) 0.07128(7) 0.0133(5) Uani 1.000
C C5 0.75149(18) 0.1147(3) 0.01826(7) 0.0127(5) Uani 1.000
C C6 0.73320(18) -0.0549(3) -0.00198(7) 0.0136(5) Uani 1.000
C C7 0.63769(19) -0.1155(3) -0.05182(8) 0.0181(6) Uani 1.000
C C8 0.68440(19) 0.2753(2) -0.00735(8) 0.0130(5) Uani 1.000
C C9 0.51398(19) 0.3921(3) -0.07597(8) 0.0193(6) Uani 1.000
C C10 0.5891(2) 0.4244(3) -0.12397(9) 0.0303(7) Uani 1.000
C C11 1.07165(18) 0.0371(3) 0.12318(8) 0.0169(6) Uani 1.000
C C12 1.1835(2) 0.2660(3) 0.18190(10) 0.0264(7) Uani 1.000
C C13 1.1395(3) 0.2357(3) 0.23741(10) 0.0292(7) Uani 1.000
C C14 0.76975(18) 0.1802(3) 0.12001(7) 0.0137(5) Uani 1.000
C C15 0.6847(2) 0.0454(3) 0.13475(8) 0.0184(6) Uani 1.000
C C16 0.6134(2) 0.0666(3) 0.17933(8) 0.0201(6) Uani 1.000
C C17 0.6288(2) 0.2243(3) 0.20965(8) 0.0170(6) Uani 1.000
C C18 0.7117(2) 0.3610(3) 0.19590(8) 0.0208(6) Uani 1.000
C C19 0.7813(2) 0.3375(3) 0.15105(8) 0.0193(6) Uani 1.000
H H1 0.78782 -0.30168 0.01486 0.0190 Uiso 1.000
H H1A 1.09448 -0.31251 0.05973 0.0305 Uiso 1.000
H H1B 0.96477 -0.43187 0.05462 0.0305 Uiso 1.000
H H1C 1.02581 -0.35245 0.11231 0.0305 Uiso 1.000
H H4 0.89637 0.26388 0.06592 0.0159 Uiso 1.000
H H7A 0.54706 -0.10591 -0.04401 0.0271 Uiso 1.000
H H7B 0.65646 -0.23841 -0.06021 0.0271 Uiso 1.000
H H7C 0.64872 -0.04066 -0.08299 0.0271 Uiso 1.000
H H9A 0.51786 0.49911 -0.05295 0.0232 Uiso 1.000
H H9B 0.42047 0.36700 -0.08950 0.0232 Uiso 1.000
H H10A 0.68067 0.45441 -0.11041 0.0455 Uiso 1.000
H H10B 0.54807 0.52207 -0.14601 0.0455 Uiso 1.000
H H10C 0.58662 0.31751 -0.14624 0.0455 Uiso 1.000
H H12A 1.20504 0.39234 0.17800 0.0317 Uiso 1.000
H H12B 1.26403 0.19640 0.17941 0.0317 Uiso 1.000
H H13A 1.05396 0.29215 0.23823 0.0437 Uiso 1.000
H H13B 1.20446 0.28677 0.26579 0.0437 Uiso 1.000
H H13C 1.13192 0.10873 0.24375 0.0437 Uiso 1.000
H H15 0.67545 -0.06086 0.11435 0.0220 Uiso 1.000
H H16 0.55656 -0.02388 0.18853 0.0241 Uiso 1.000
H H18 0.72077 0.46701 0.21640 0.0249 Uiso 1.000
H H19 0.83673 0.42932 0.14163 0.0232 Uiso 1.000
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'
Cl Cl 0.1484 0.1585 '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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C11 O2 C12 117.15(16) no
C8 O4 C9 116.32(14) no
C2 N1 C6 123.64(17) no
C6 N1 H1 118.00 no
C2 N1 H1 118.00 no
N1 C2 C3 119.37(18) no
N1 C2 C1 113.54(18) no
C1 C2 C3 127.07(18) no
C4 C3 C11 118.21(18) no
C2 C3 C4 120.71(17) no
C2 C3 C11 120.87(19) no
C3 C4 C14 110.84(16) no
C3 C4 C5 111.13(17) no
C5 C4 C14 110.44(15) no
C4 C5 C8 114.20(18) no
C4 C5 C6 121.03(18) no
C6 C5 C8 124.76(16) no
N1 C6 C7 113.35(18) no
C5 C6 C7 127.52(18) no
N1 C6 C5 119.10(16) no
O4 C8 C5 114.28(14) no
O3 C8 O4 122.29(16) no
O3 C8 C5 123.41(18) no
O4 C9 C10 109.88(16) no
O2 C11 C3 110.57(17) no
O1 C11 C3 127.0(2) no
O1 C11 O2 122.40(18) no
O2 C12 C13 111.17(18) no
C15 C14 C19 118.05(17) no
C4 C14 C15 120.27(18) no
C4 C14 C19 121.69(18) no
C14 C15 C16 121.44(19) no
C15 C16 C17 118.8(2) no
Br C17 C18 119.27(16) no
Br C17 C16 119.56(16) no
C16 C17 C18 121.17(19) no
C17 C18 C19 119.1(2) no
C14 C19 C18 121.46(19) no
C2 C1 H1A 109.00 no
C2 C1 H1B 109.00 no
C2 C1 H1C 109.00 no
H1A C1 H1B 109.00 no
H1A C1 H1C 110.00 no
H1B C1 H1C 109.00 no
C3 C4 H4 108.00 no
C5 C4 H4 108.00 no
C14 C4 H4 108.00 no
C6 C7 H7A 109.00 no
C6 C7 H7B 109.00 no
C6 C7 H7C 109.00 no
H7A C7 H7B 109.00 no
H7A C7 H7C 109.00 no
H7B C7 H7C 109.00 no
O4 C9 H9A 110.00 no
O4 C9 H9B 110.00 no
C10 C9 H9A 110.00 no
C10 C9 H9B 110.00 no
H9A C9 H9B 108.00 no
C9 C10 H10A 109.00 no
C9 C10 H10B 109.00 no
C9 C10 H10C 109.00 no
H10A C10 H10B 109.00 no
H10A C10 H10C 109.00 no
H10B C10 H10C 109.00 no
O2 C12 H12A 109.00 no
O2 C12 H12B 109.00 no
C13 C12 H12A 109.00 no
C13 C12 H12B 109.00 no
H12A C12 H12B 108.00 no
C12 C13 H13A 109.00 no
C12 C13 H13B 109.00 no
C12 C13 H13C 109.00 no
H13A C13 H13B 109.00 no
H13A C13 H13C 109.00 no
H13B C13 H13C 109.00 no
C14 C15 H15 119.00 no
C16 C15 H15 119.00 no
C15 C16 H16 121.00 no
C17 C16 H16 121.00 no
C17 C18 H18 120.00 no
C19 C18 H18 120.00 no
C14 C19 H19 119.00 no
C18 C19 H19 119.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br C17 1.902(2) no
O1 C11 1.214(2) no
O2 C11 1.356(3) no
O2 C12 1.453(3) no
O3 C8 1.218(2) no
O4 C8 1.347(2) no
O4 C9 1.457(3) no
N1 C2 1.386(3) no
N1 C6 1.380(3) no
N1 H1 0.8600 no
C1 C2 1.503(3) no
C2 C3 1.355(3) no
C3 C11 1.473(3) no
C3 C4 1.522(3) no
C4 C14 1.527(2) no
C4 C5 1.527(2) no
C5 C6 1.355(3) no
C5 C8 1.466(3) no
C6 C7 1.507(3) no
C9 C10 1.499(3) no
C12 C13 1.499(3) no
C14 C19 1.387(3) no
C14 C15 1.396(3) no
C15 C16 1.393(3) no
C16 C17 1.382(3) no
C17 C18 1.385(3) no
C18 C19 1.390(3) no
C1 H1A 0.9600 no
C1 H1B 0.9600 no
C1 H1C 0.9600 no
C4 H4 0.9800 no
C7 H7A 0.9600 no
C7 H7B 0.9600 no
C7 H7C 0.9600 no
C9 H9A 0.9700 no
C9 H9B 0.9700 no
C10 H10A 0.9600 no
C10 H10B 0.9600 no
C10 H10C 0.9600 no
C12 H12A 0.9700 no
C12 H12B 0.9700 no
C13 H13A 0.9600 no
C13 H13B 0.9600 no
C13 H13C 0.9600 no
C15 H15 0.9300 no
C16 H16 0.9300 no
C18 H18 0.9300 no
C19 H19 0.9300 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
N1 H1 O3 1_545 0.86 2.11 2.969(2) 173 yes
C4 H4 O3 . 0.98 2.47 2.811(2) 100 yes
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
C11 O2 C12 C13 -83.5(2) no
C12 O2 C11 O1 -7.9(3) no
C12 O2 C11 C3 171.77(16) no
C8 O4 C9 C10 80.4(2) no
C9 O4 C8 O3 10.3(3) no
C9 O4 C8 C5 -171.06(15) no
C6 N1 C2 C1 -166.26(17) no
C6 N1 C2 C3 12.1(3) no
C2 N1 C6 C5 -12.9(3) no
C2 N1 C6 C7 165.30(17) no
C1 C2 C3 C11 -0.3(3) no
N1 C2 C3 C4 6.9(3) no
N1 C2 C3 C11 -178.42(17) no
C1 C2 C3 C4 -174.97(18) no
C2 C3 C4 C14 101.3(2) no
C11 C3 C4 C5 163.28(17) no
C11 C3 C4 C14 -73.5(2) no
C2 C3 C11 O1 -3.2(3) no
C2 C3 C11 O2 177.10(17) no
C4 C3 C11 O1 171.59(19) no
C4 C3 C11 O2 -8.1(2) no
C2 C3 C4 C5 -21.9(2) no
C3 C4 C5 C6 21.2(2) no
C3 C4 C5 C8 -158.58(16) no
C14 C4 C5 C6 -102.3(2) no
C14 C4 C5 C8 78.0(2) no
C3 C4 C14 C15 -65.5(2) no
C3 C4 C14 C19 114.0(2) no
C5 C4 C14 C15 58.1(2) no
C5 C4 C14 C19 -122.3(2) no
C4 C5 C6 C7 176.77(17) no
C8 C5 C6 N1 174.40(17) no
C8 C5 C6 C7 -3.5(3) no
C4 C5 C8 O3 17.5(3) no
C4 C5 C8 O4 -161.12(16) no
C6 C5 C8 O3 -162.23(19) no
C6 C5 C8 O4 19.1(3) no
C4 C5 C6 N1 -5.4(3) no
C4 C14 C15 C16 179.40(18) no
C19 C14 C15 C16 -0.2(3) no
C4 C14 C19 C18 -178.99(18) no
C15 C14 C19 C18 0.6(3) no
C14 C15 C16 C17 -0.6(3) no
C15 C16 C17 Br -179.49(15) no
C15 C16 C17 C18 1.0(3) no
Br C17 C18 C19 179.87(15) no
C16 C17 C18 C19 -0.6(3) no
C17 C18 C19 C14 -0.2(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 856318
