#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/42/2014220.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_2014220
loop_
_publ_author_name
'Belmar, Julio'
'Pérez, Fredy R.'
'Moreno, Yanko'
'Baggio, Ricardo'
_publ_section_title
;
 Two enamines derived from 1-n-alkyl-3-methylpyrazol-5-ones
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o705
_journal_page_last               o708
_journal_paper_doi               10.1107/S0108270104018736
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C19 H27 N3 O'
_chemical_formula_moiety         'C19 H27 N3 O'
_chemical_formula_sum            'C19 H27 N3 O'
_chemical_formula_weight         313.44
_chemical_name_systematic
;
1-(n-hexyl)-3-methyl-4-(1-phenylaminopropylidene)-2-pyrazolin-5-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                85.111(2)
_cell_angle_beta                 68.812(2)
_cell_angle_gamma                78.911(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0221(14)
_cell_length_b                   9.1427(14)
_cell_length_c                   11.9077(18)
_cell_measurement_reflns_used    2388
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      50.08
_cell_measurement_theta_min      4.54
_cell_volume                     898.6(2)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1994)'
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART 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  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5601
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.83
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prisms
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.278
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3132
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0865P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1330
_refine_ls_wR_factor_ref         0.1584
_reflns_number_gt                2155
_reflns_number_total             3132
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob1196.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' 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-1
_cod_database_code               2014220
_cod_database_fobs_code          2014220
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O1 0.33453(18) 0.88340(16) 0.28489(13) 0.0709(4) Uani d . 1 . . O
N1 0.20236(19) 1.12682(18) 0.28119(15) 0.0631(5) Uani d . 1 . . N
N2 0.11541(18) 1.24112(18) 0.36057(16) 0.0641(5) Uani d . 1 . . N
N3 0.31692(18) 0.80665(16) 0.51385(14) 0.0571(4) Uani d . 1 . . N
H3N 0.3499 0.7887 0.4382 0.068 Uiso calc R 1 . . H
C1 0.2555(2) 1.0027(2) 0.33617(18) 0.0561(5) Uani d . 1 . . C
C2 0.1989(2) 1.03999(19) 0.46136(17) 0.0502(5) Uani d . 1 . . C
C3 0.1115(2) 1.1902(2) 0.46784(18) 0.0557(5) Uani d . 1 . . C
C4 0.0217(3) 1.2879(2) 0.5722(2) 0.0735(6) Uani d . 1 . . C
H4A -0.0248 1.3814 0.5454 0.110 Uiso calc R 1 . . H
H4B 0.0940 1.3047 0.6104 0.110 Uiso calc R 1 . . H
H4C -0.0626 1.2409 0.6287 0.110 Uiso calc R 1 . . H
C5 0.2296(2) 0.94039(19) 0.54886(16) 0.0496(5) Uani d . 1 . . C
C6 0.1784(2) 0.9790(2) 0.67776(17) 0.0580(5) Uani d . 1 . . C
H6A 0.1634 0.8892 0.7272 0.070 Uiso calc R 1 . . H
H6B 0.0758 1.0467 0.7007 0.070 Uiso calc R 1 . . H
C7 0.3026(3) 1.0515(2) 0.7010(2) 0.0765(7) Uani d . 1 . . C
H7A 0.2678 1.0719 0.7853 0.115 Uiso calc R 1 . . H
H7B 0.3135 1.1431 0.6553 0.115 Uiso calc R 1 . . H
H7C 0.4047 0.9854 0.6771 0.115 Uiso calc R 1 . . H
C8 0.3616(2) 0.68928(19) 0.58946(16) 0.0515(5) Uani d . 1 . . C
C9 0.2538(2) 0.5986(2) 0.65451(18) 0.0618(5) Uani d . 1 . . C
H9A 0.1500 0.6150 0.6521 0.074 Uiso calc R 1 . . H
C10 0.3010(3) 0.4830(2) 0.72332(19) 0.0701(6) Uani d . 1 . . C
H10A 0.2284 0.4215 0.7677 0.084 Uiso calc R 1 . . H
C11 0.4541(3) 0.4578(2) 0.72692(19) 0.0701(6) Uani d . 1 . . C
H11A 0.4853 0.3796 0.7734 0.084 Uiso calc R 1 . . H
C12 0.5602(3) 0.5480(2) 0.6620(2) 0.0734(6) Uani d . 1 . . C
H12A 0.6643 0.5306 0.6638 0.088 Uiso calc R 1 . . H
C13 0.5143(2) 0.6649(2) 0.59368(19) 0.0639(6) Uani d . 1 . . C
H13A 0.5868 0.7270 0.5505 0.077 Uiso calc R 1 . . H
C14 0.2228(3) 1.1460(3) 0.15446(19) 0.0770(7) Uani d . 1 . . C
H14A 0.1190 1.1876 0.1476 0.092 Uiso calc R 1 . . H
H14B 0.2583 1.0490 0.1173 0.092 Uiso calc R 1 . . H
C15 0.3426(3) 1.2461(3) 0.0859(2) 0.0824(7) Uani d . 1 . . C
H15A 0.3467 1.2560 0.0032 0.099 Uiso calc R 1 . . H
H15B 0.3046 1.3444 0.1209 0.099 Uiso calc R 1 . . H
C16 0.5102(3) 1.1905(2) 0.0865(2) 0.0753(6) Uani d . 1 . . C
H16A 0.5436 1.0883 0.0593 0.090 Uiso calc R 1 . . H
H16B 0.5075 1.1900 0.1686 0.090 Uiso calc R 1 . . H
C17 0.6347(3) 1.2811(3) 0.0084(2) 0.0798(7) Uani d . 1 . . C
H17A 0.6440 1.2747 -0.0748 0.096 Uiso calc R 1 . . H
H17B 0.5972 1.3848 0.0312 0.096 Uiso calc R 1 . . H
C18 0.7992(3) 1.2321(3) 0.0173(2) 0.0925(8) Uani d . 1 . . C
H18A 0.7889 1.2358 0.1010 0.111 Uiso calc R 1 . . H
H18B 0.8374 1.1290 -0.0072 0.111 Uiso calc R 1 . . H
C19 0.9231(3) 1.3219(4) -0.0564(3) 0.1162(10) Uani d . 1 . . C
H19A 1.0230 1.2846 -0.0439 0.174 Uiso calc R 1 . . H
H19B 0.8872 1.4242 -0.0328 0.174 Uiso calc R 1 . . H
H19C 0.9389 1.3148 -0.1401 0.174 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
C1 N1 N2 112.89(16)
C1 N1 C14 127.03(19)
N2 N1 C14 120.04(16)
C3 N2 N1 106.42(15)
C5 N3 C8 126.59(16)
C5 N3 H3N 116.7
C8 N3 H3N 116.7
O1 C1 N1 125.42(19)
O1 C1 C2 129.71(17)
N1 C1 C2 104.86(17)
C5 C2 C1 122.63(16)
C5 C2 C3 132.34(18)
C1 C2 C3 105.03(15)
N2 C3 C2 110.79(18)
N2 C3 C4 118.51(18)
C2 C3 C4 130.70(18)
C3 C4 H4A 109.5
C3 C4 H4B 109.5
H4A C4 H4B 109.5
C3 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
N3 C5 C2 118.10(17)
N3 C5 C6 118.36(15)
C2 C5 C6 123.43(16)
C5 C6 C7 111.51(15)
C5 C6 H6A 109.3
C7 C6 H6A 109.3
C5 C6 H6B 109.3
C7 C6 H6B 109.3
H6A C6 H6B 108.0
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C13 C8 C9 120.04(17)
C13 C8 N3 119.64(17)
C9 C8 N3 120.29(16)
C8 C9 C10 119.42(19)
C8 C9 H9A 120.3
C10 C9 H9A 120.3
C11 C10 C9 120.6(2)
C11 C10 H10A 119.7
C9 C10 H10A 119.7
C12 C11 C10 119.61(18)
C12 C11 H11A 120.2
C10 C11 H11A 120.2
C11 C12 C13 120.49(19)
C11 C12 H12A 119.8
C13 C12 H12A 119.8
C8 C13 C12 119.86(18)
C8 C13 H13A 120.1
C12 C13 H13A 120.1
N1 C14 C15 113.81(18)
N1 C14 H14A 108.8
C15 C14 H14A 108.8
N1 C14 H14B 108.8
C15 C14 H14B 108.8
H14A C14 H14B 107.7
C16 C15 C14 113.80(18)
C16 C15 H15A 108.8
C14 C15 H15A 108.8
C16 C15 H15B 108.8
C14 C15 H15B 108.8
H15A C15 H15B 107.7
C15 C16 C17 114.42(18)
C15 C16 H16A 108.7
C17 C16 H16A 108.7
C15 C16 H16B 108.7
C17 C16 H16B 108.7
H16A C16 H16B 107.6
C18 C17 C16 114.03(19)
C18 C17 H17A 108.7
C16 C17 H17A 108.7
C18 C17 H17B 108.7
C16 C17 H17B 108.7
H17A C17 H17B 107.6
C19 C18 C17 115.1(2)
C19 C18 H18A 108.5
C17 C18 H18A 108.5
C19 C18 H18B 108.5
C17 C18 H18B 108.5
H18A C18 H18B 107.5
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 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
O1 C1 . 1.253(2) y
N1 C1 . 1.355(2) y
N1 N2 . 1.385(2) y
N1 C14 . 1.452(3) y
N2 C3 . 1.312(2) y
N3 C5 . 1.330(2) y
N3 C8 . 1.434(2) y
N3 H3N . 0.8600 ?
C1 C2 . 1.438(3) y
C2 C5 . 1.394(2) y
C2 C3 . 1.439(2) y
C3 C4 . 1.477(3) y
C4 H4A . 0.9600 ?
C4 H4B . 0.9600 ?
C4 H4C . 0.9600 ?
C5 C6 . 1.487(3) no
C6 C7 . 1.521(3) no
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 C13 . 1.372(3) no
C8 C9 . 1.375(2) no
C9 C10 . 1.379(3) no
C9 H9A . 0.9300 ?
C10 C11 . 1.372(3) no
C10 H10A . 0.9300 ?
C11 C12 . 1.361(3) no
C11 H11A . 0.9300 ?
C12 C13 . 1.378(3) no
C12 H12A . 0.9300 ?
C13 H13A . 0.9300 ?
C14 C15 . 1.512(3) no
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 C16 . 1.501(3) no
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 C17 . 1.512(3) no
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 C18 . 1.504(3) no
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 C19 . 1.488(3) no
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N3 H3N O1 0.86 1.99 2.712(2) 141
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652399
