#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/49/2204921.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_2204921
loop_
_publ_author_name
'Howie, R. Alan'
'Kindness, Andrew'
'McKay, Michael G.'
'Maguire, Glenn E. M.'
_publ_section_title
;
 (Anthracen-9-ylmethyl)diethylamine at 100K
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o52
_journal_page_last               o54
_journal_paper_doi               10.1107/S1600536804031265
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C19 H21 N'
_chemical_formula_moiety         'C19 H21 N'
_chemical_formula_sum            'C19 H21 N'
_chemical_formula_weight         263.37
_chemical_melting_point          .36E-305
_chemical_name_systematic
;
(Anthracen-9-ylmethyl)diethylamine at 100K
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 93.388(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5230(10)
_cell_length_b                   22.678(5)
_cell_length_c                   7.769(2)
_cell_measurement_reflns_used    2017
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32
_cell_measurement_theta_min      4
_cell_volume                     1499.0(5)
_computing_cell_refinement       'CrysAlis CCD'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2003)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2003)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_device_type  'Xcalibur2 area-detector'
_diffrn_measurement_method       ω-2θ
_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  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14548
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         31.91
_diffrn_reflns_theta_min         4.32
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         4796
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0476
_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)+(0.0802P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1367
_reflns_number_gt                3585
_reflns_number_total             4796
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6328.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2204921
_cod_database_fobs_code          2204921
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_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_type_symbol
N1 0.28466(10) 0.45869(4) 0.77896(10) 0.01573(18) Uani d . 1 N
C1 0.32807(10) 0.36296(4) 0.63016(11) 0.01304(18) Uani d . 1 C
C2 0.25325(11) 0.34470(4) 0.47101(11) 0.01319(18) Uani d . 1 C
C3 0.09093(11) 0.35617(4) 0.42278(12) 0.0178(2) Uani d . 1 C
H3 0.0298 0.3783 0.4982 0.021 Uiso calc R 1 H
C4 0.02237(12) 0.33592(5) 0.27049(13) 0.0214(2) Uani d . 1 C
H4 -0.0858 0.3437 0.2431 0.026 Uiso calc R 1 H
C5 0.11017(12) 0.30347(5) 0.15230(13) 0.0209(2) Uani d . 1 C
H5 0.0606 0.2894 0.0475 0.025 Uiso calc R 1 H
C6 0.26519(12) 0.29265(4) 0.19013(12) 0.0177(2) Uani d . 1 C
H6 0.3240 0.2718 0.1096 0.021 Uiso calc R 1 H
C7 0.34132(11) 0.31209(4) 0.34929(11) 0.01392(18) Uani d . 1 C
C8 0.49882(11) 0.29836(4) 0.38961(12) 0.01495(19) Uani d . 1 C
H8 0.5561 0.2769 0.3091 0.018 Uiso calc R 1 H
C9 0.57381(10) 0.31564(4) 0.54650(11) 0.01381(18) Uani d . 1 C
C10 0.73430(11) 0.30030(4) 0.58820(12) 0.0170(2) Uani d . 1 C
H10 0.7900 0.2776 0.5092 0.020 Uiso calc R 1 H
C11 0.80842(11) 0.31788(4) 0.73983(13) 0.0195(2) Uani d . 1 C
H11 0.9150 0.3073 0.7660 0.023 Uiso calc R 1 H
C12 0.72597(12) 0.35206(4) 0.85905(13) 0.0206(2) Uani d . 1 C
H12 0.7789 0.3647 0.9637 0.025 Uiso calc R 1 H
C13 0.57198(11) 0.36699(4) 0.82513(12) 0.0176(2) Uani d . 1 C
H13 0.5193 0.3896 0.9070 0.021 Uiso calc R 1 H
C14 0.48826(11) 0.34909(4) 0.66770(11) 0.01342(18) Uani d . 1 C
C15 0.23994(11) 0.39603(4) 0.76462(12) 0.01584(19) Uani d . 1 C
H15A 0.1257 0.3933 0.7344 0.019 Uiso calc R 1 H
H15B 0.2607 0.3768 0.8781 0.019 Uiso calc R 1 H
C16 0.23523(12) 0.49040(4) 0.61903(13) 0.0197(2) Uani d . 1 C
H16A 0.1205 0.4975 0.6171 0.024 Uiso calc R 1 H
H16B 0.2560 0.4651 0.5190 0.024 Uiso calc R 1 H
C17 0.31859(14) 0.54901(5) 0.60020(14) 0.0264(2) Uani d . 1 C
H17A 0.2947 0.5750 0.6961 0.040 Uiso calc R 1 H
H17B 0.2826 0.5675 0.4909 0.040 Uiso calc R 1 H
H17C 0.4323 0.5424 0.6015 0.040 Uiso calc R 1 H
C18 0.21012(12) 0.48517(5) 0.92764(13) 0.0233(2) Uani d . 1 C
H18A 0.0989 0.4725 0.9252 0.028 Uiso calc R 1 H
H18B 0.2113 0.5286 0.9154 0.028 Uiso calc R 1 H
C19 0.28961(15) 0.46879(5) 1.10158(13) 0.0280(3) Uani d . 1 C
H19A 0.2835 0.4260 1.1181 0.042 Uiso calc R 1 H
H19B 0.2365 0.4888 1.1935 0.042 Uiso calc R 1 H
H19C 0.4001 0.4810 1.1052 0.042 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'
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
C15 N1 C16 110.27(7) y
C15 N1 C18 109.24(8) y
C16 N1 C18 110.22(8) y
C14 C1 C2 119.56(8) ?
C14 C1 C15 118.57(8) y
C2 C1 C15 121.86(8) y
C1 C2 C3 123.44(8) ?
C1 C2 C7 119.70(8) ?
C3 C2 C7 116.86(8) ?
C4 C3 C2 121.39(9) ?
C4 C3 H3 119.3 ?
C2 C3 H3 119.3 ?
C3 C4 C5 121.17(9) ?
C3 C4 H4 119.4 ?
C5 C4 H4 119.4 ?
C6 C5 C4 119.69(9) ?
C6 C5 H5 120.2 ?
C4 C5 H5 120.2 ?
C5 C6 C7 121.10(9) ?
C5 C6 H6 119.4 ?
C7 C6 H6 119.4 ?
C8 C7 C6 120.41(8) ?
C8 C7 C2 119.82(8) ?
C6 C7 C2 119.75(8) ?
C7 C8 C9 121.15(8) ?
C7 C8 H8 119.4 ?
C9 C8 H8 119.4 ?
C8 C9 C10 120.74(8) ?
C8 C9 C14 119.63(8) ?
C10 C9 C14 119.63(8) ?
C11 C10 C9 120.86(9) ?
C11 C10 H10 119.6 ?
C9 C10 H10 119.6 ?
C10 C11 C12 119.99(9) ?
C10 C11 H11 120.0 ?
C12 C11 H11 120.0 ?
C13 C12 C11 120.98(9) ?
C13 C12 H12 119.5 ?
C11 C12 H12 119.5 ?
C12 C13 C14 121.14(9) ?
C12 C13 H13 119.4 ?
C14 C13 H13 119.4 ?
C1 C14 C13 122.49(8) ?
C1 C14 C9 120.13(8) ?
C13 C14 C9 117.38(8) ?
N1 C15 C1 113.06(7) y
N1 C15 H15A 109.0 ?
C1 C15 H15A 109.0 ?
N1 C15 H15B 109.0 ?
C1 C15 H15B 109.0 ?
H15A C15 H15B 107.8 ?
N1 C16 C17 113.32(8) y
N1 C16 H16A 108.9 ?
C17 C16 H16A 108.9 ?
N1 C16 H16B 108.9 ?
C17 C16 H16B 108.9 ?
H16A C16 H16B 107.7 ?
C16 C17 H17A 109.5 ?
C16 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C16 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
N1 C18 C19 113.92(9) y
N1 C18 H18A 108.8 ?
C19 C18 H18A 108.8 ?
N1 C18 H18B 108.8 ?
C19 C18 H18B 108.8 ?
H18A C18 H18B 107.7 ?
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_distance
_geom_bond_publ_flag
N1 C15 1.4738(12) y
N1 C16 1.4753(13) y
N1 C18 1.4782(12) y
C1 C14 1.4146(13) ?
C1 C2 1.4191(12) ?
C1 C15 1.5201(13) y
C2 C3 1.4355(13) ?
C2 C7 1.4451(13) ?
C3 C4 1.3677(14) ?
C3 H3 0.9500 ?
C4 C5 1.4234(15) ?
C4 H4 0.9500 ?
C5 C6 1.3588(14) ?
C5 H5 0.9500 ?
C6 C7 1.4316(13) ?
C6 H6 0.9500 ?
C7 C8 1.3954(13) ?
C8 C9 1.3984(13) ?
C8 H8 0.9500 ?
C9 C10 1.4299(13) ?
C9 C14 1.4403(13) ?
C10 C11 1.3630(13) ?
C10 H10 0.9500 ?
C11 C12 1.4246(15) ?
C11 H11 0.9500 ?
C12 C13 1.3659(14) ?
C12 H12 0.9500 ?
C13 C14 1.4376(13) ?
C13 H13 0.9500 ?
C15 H15A 0.9900 ?
C15 H15B 0.9900 ?
C16 C17 1.5183(15) y
C16 H16A 0.9900 ?
C16 H16B 0.9900 ?
C17 H17A 0.9800 ?
C17 H17B 0.9800 ?
C17 H17C 0.9800 ?
C18 C19 1.5215(15) y
C18 H18A 0.9900 ?
C18 H18B 0.9900 ?
C19 H19A 0.9800 ?
C19 H19B 0.9800 ?
C19 H19C 0.9800 ?
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
C2 C1 C15 N1 -107.99(9) y
C14 C1 C15 N1 73.42(10) y
C1 C15 N1 C16 66.38(10) y
C1 C15 N1 C18 -172.35(8) y
C15 N1 C16 C17 -162.17(8) y
C15 N1 C18 C19 76.45(11) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13190270
