#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/18/2201885.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_2201885
loop_
_publ_author_name
Ompraba
'A. Aysha'
'M. Yogavel'
'D. Velmurugan'
'S. Selvi'
'P. T. Perumal'
'S. Shanmuga Sundara Raj'
'H.-K. Fun'
'Z. A. Rafi'
_publ_section_title
;
 2-Cyano-3-dimethylamino-N-(2,5-dimethylphenyl)acrylamide
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o353
_journal_page_last               o355
_journal_paper_doi               10.1107/S1600536803002848
_journal_volume                  59
_journal_year                    2003
_chemical_formula_moiety         'C14 H17 N3 O'
_chemical_formula_sum            'C14 H17 N3 O'
_chemical_formula_weight         243.31
_chemical_name_systematic
;
2-cyano-3-dimethylamino-N-(2,5-methylphenyl)acrylamide
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.079(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9315(2)
_cell_length_b                   11.8940(4)
_cell_length_c                   11.3979(4)
_cell_measurement_reflns_used    3509
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.48
_cell_volume                     1336.12(8)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990)
;
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type
;
Siemens SMART CCD area-detector diffractometer
;
_diffrn_measurement_method       'ω scans'
_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  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0487
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9076
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.48
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.164
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3291
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0581
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w = 1/[σ²(Fo²)+(0.0822P)²+0.1140P] where P = (Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1677
_reflns_number_gt                2001
_reflns_number_total             3291
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6200.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2201885
_cod_database_fobs_code          2201885
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_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
_atom_site_type_symbol
C1 0.38358(17) 0.50888(14) 0.66130(15) 0.0450(4) Uani d . 1 . . C
C2 0.45239(19) 0.54894(16) 0.76825(16) 0.0535(5) Uani d . 1 . . C
C3 0.3961(2) 0.64001(18) 0.82077(19) 0.0685(6) Uani d . 1 . . C
H3 0.4393 0.6675 0.8920 0.082 Uiso calc R 1 . . H
C4 0.2782(3) 0.69105(18) 0.7708(2) 0.0705(6) Uani d . 1 . . C
H4 0.2439 0.7524 0.8082 0.085 Uiso calc R 1 . . H
C5 0.2106(2) 0.65193(17) 0.66578(19) 0.0606(5) Uani d . 1 . . C
C6 0.26400(19) 0.56044(15) 0.61184(16) 0.0518(5) Uani d . 1 . . C
H6 0.2190 0.5330 0.5412 0.062 Uiso calc R 1 . . H
N7 0.44063(14) 0.41613(12) 0.60818(12) 0.0474(4) Uani d . 1 . . N
H7 0.5174 0.3935 0.6435 0.057 Uiso calc R 1 . . H
C8 0.39277(17) 0.35672(14) 0.50932(15) 0.0454(4) Uani d . 1 . . C
O9 0.28856(15) 0.38084(14) 0.44681(13) 0.0780(5) Uani d . 1 . . O
C10 0.47713(16) 0.25864(14) 0.48407(15) 0.0435(4) Uani d . 1 . . C
C11 0.5921(2) 0.23470(15) 0.56674(17) 0.0527(5) Uani d . 1 . . C
N12 0.6826(2) 0.22280(18) 0.63869(19) 0.0839(6) Uani d . 1 . . N
C13 0.43875(17) 0.20134(14) 0.38065(16) 0.0460(4) Uani d . 1 . . C
H13 0.3627 0.2305 0.3350 0.055 Uiso calc R 1 . . H
N14 0.49174(15) 0.11173(13) 0.33516(13) 0.0530(4) Uani d . 1 . . N
C15 0.4362(2) 0.0697(2) 0.2195(2) 0.0771(7) Uani d . 1 . . C
H15A 0.3611 0.1159 0.1880 0.116 Uiso calc R 1 . . H
H15B 0.4058 -0.0063 0.2269 0.116 Uiso calc R 1 . . H
H15C 0.5051 0.0718 0.1674 0.116 Uiso calc R 1 . . H
C16 0.6128(2) 0.05418(19) 0.3892(2) 0.0690(6) Uani d . 1 . . C
H16A 0.6916 0.0974 0.3770 0.103 Uiso calc R 1 . . H
H16B 0.6182 -0.0186 0.3537 0.103 Uiso calc R 1 . . H
H16C 0.6086 0.0458 0.4724 0.103 Uiso calc R 1 . . H
C17 0.5851(2) 0.4988(2) 0.8222(2) 0.0729(6) Uani d . 1 . . C
H17A 0.6546 0.5165 0.7736 0.109 Uiso calc R 1 . . H
H17B 0.5759 0.4186 0.8273 0.109 Uiso calc R 1 . . H
H17C 0.6092 0.5292 0.8999 0.109 Uiso calc R 1 . . H
C18 0.0825(3) 0.7079(2) 0.6096(3) 0.0878(8) Uani d . 1 . . C
H18A 0.1053 0.7685 0.5600 0.132 Uiso calc R 1 . . H
H18B 0.0330 0.7369 0.6703 0.132 Uiso calc R 1 . . H
H18C 0.0276 0.6540 0.5628 0.132 Uiso calc R 1 . . 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
C6 C1 C2 120.08(17) ?
C6 C1 N7 122.57(16) y
C2 C1 N7 117.35(16) ?
C3 C2 C1 117.38(18) ?
C3 C2 C17 120.79(18) ?
C1 C2 C17 121.79(18) ?
C4 C3 C2 122.2(2) ?
C4 C3 H3 118.9 ?
C2 C3 H3 118.9 ?
C3 C4 C5 120.5(2) ?
C3 C4 H4 119.7 ?
C5 C4 H4 119.7 ?
C4 C5 C6 118.5(2) ?
C4 C5 C18 121.0(2) ?
C6 C5 C18 120.5(2) ?
C5 C6 C1 121.31(19) ?
C5 C6 H6 119.3 ?
C1 C6 H6 119.3 ?
C8 N7 C1 129.93(14) y
C8 N7 H7 115.0 ?
C1 N7 H7 115.0 ?
O9 C8 N7 123.11(16) y
O9 C8 C10 122.10(16) ?
N7 C8 C10 114.79(14) y
C13 C10 C11 125.91(16) y
C13 C10 C8 116.89(15) y
C11 C10 C8 117.17(15) ?
N12 C11 C10 174.5(2) ?
N14 C13 C10 130.86(16) y
N14 C13 H13 114.6 ?
C10 C13 H13 114.6 ?
C13 N14 C15 120.53(16) y
C13 N14 C16 124.21(16) y
C15 N14 C16 115.07(16) y
N14 C15 H15A 109.5 ?
N14 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
N14 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
N14 C16 H16A 109.5 ?
N14 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
N14 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
C2 C17 H17A 109.5 ?
C2 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C2 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
C5 C18 H18A 109.5 ?
C5 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
C5 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
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 C6 . 1.393(2) ?
C1 C2 . 1.405(2) ?
C1 N7 . 1.410(2) y
C2 C3 . 1.388(3) ?
C2 C17 . 1.507(3) ?
C3 C4 . 1.378(3) ?
C3 H3 . 0.93 ?
C4 C5 . 1.379(3) ?
C4 H4 . 0.93 ?
C5 C6 . 1.387(3) ?
C5 C18 . 1.507(3) ?
C6 H6 . 0.93 ?
N7 C8 . 1.365(2) y
N7 H7 . 0.86 ?
C8 O9 . 1.216(2) y
C8 C10 . 1.485(2) y
C10 C13 . 1.374(2) y
C10 C11 . 1.417(3) y
C11 N12 . 1.148(2) y
C13 N14 . 1.323(2) y
C13 H13 . 0.93 ?
N14 C15 . 1.453(2) y
N14 C16 . 1.453(2) y
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?
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
N7 H7 N12 . 0.86 2.62 3.313(2) 139
C6 H6 O9 . 0.93 2.26 2.876(2) 124
C13 H13 O9 . 0.93 2.37 2.762(2) 105
C15 H15A N12 4_565 0.96 2.63 3.566(3) 166
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
C6 C1 C2 C3 0.2(3) ?
N7 C1 C2 C3 -179.80(15) ?
C6 C1 C2 C17 -177.38(17) ?
N7 C1 C2 C17 2.6(3) ?
C1 C2 C3 C4 -0.7(3) ?
C17 C2 C3 C4 176.9(2) ?
C2 C3 C4 C5 0.6(3) ?
C3 C4 C5 C6 0.0(3) ?
C3 C4 C5 C18 -179.3(2) ?
C4 C5 C6 C1 -0.4(3) ?
C18 C5 C6 C1 178.84(18) ?
C2 C1 C6 C5 0.3(3) ?
N7 C1 C6 C5 -179.66(16) ?
C6 C1 N7 C8 -4.0(3) y
C2 C1 N7 C8 176.02(16) ?
C1 N7 C8 O9 3.1(3) ?
C1 N7 C8 C10 -176.25(15) y
O9 C8 C10 C13 5.5(3) ?
N7 C8 C10 C13 -175.17(15) y
O9 C8 C10 C11 -176.38(18) ?
N7 C8 C10 C11 2.9(2) ?
C11 C10 C13 N14 2.8(3) ?
C8 C10 C13 N14 -179.30(17) y
C10 C13 N14 C15 -176.65(19) ?
C10 C13 N14 C16 -1.9(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654686
