#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/47/2234769.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_2234769
loop_
_publ_author_name
'Li, Yueqing'
'Zhang, Xu'
'Huo, Shiyong'
'Huang, Wei'
'Zhao, Weijie'
_publ_section_title
;
 1-(3,5-Dimethoxybenzyl)-1H-pyrrole
;
_journal_coeditor_code           RK2345
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1372
_journal_paper_doi               10.1107/S1600536812015024
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C13 H15 N O2'
_chemical_formula_moiety         'C13 H15 N O2'
_chemical_formula_sum            'C13 H15 N O2'
_chemical_formula_weight         217.26
_chemical_name_systematic
;
1-(3,5-Dimethoxybenzyl)-1H-pyrrole
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.720(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7569(11)
_cell_length_b                   12.2303(10)
_cell_length_c                   10.4181(10)
_cell_measurement_reflns_used    2351
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      2.8
_cell_volume                     1138.2(2)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and 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  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7643
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.175
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2230
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1402
_reflns_number_gt                1717
_reflns_number_total             2230
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rk2345.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2234769
_cod_database_fobs_code          2234769
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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
N N 0.14877(13) 0.21993(9) 0.87889(11) 0.0396(3) Uani d . 1 1
O O1 0.13871(14) 0.44438(8) 0.47582(11) 0.0572(4) Uani d . 1 1
O O2 0.08702(13) 0.07035(8) 0.30839(10) 0.0536(3) Uani d . 1 1
C C11 0.13905(15) 0.11206(11) 0.54195(14) 0.0397(4) Uani d . 1 1
H H11A 0.1407 0.0373 0.5591 0.048 Uiso calc R 1 1
C C7 0.16360(16) 0.29689(11) 0.62375(14) 0.0407(4) Uani d . 1 1
H H7A 0.1814 0.3469 0.6959 0.049 Uiso calc R 1 1
C C9 0.10819(16) 0.26083(11) 0.37960(14) 0.0384(4) Uani d . 1 1
H H9A 0.0884 0.2858 0.2895 0.046 Uiso calc R 1 1
C C5 0.19169(18) 0.14323(12) 0.79460(15) 0.0478(4) Uani d . 1 1
H H5A 0.1358 0.0759 0.7850 0.057 Uiso calc R 1 1
H H5B 0.2971 0.1261 0.8437 0.057 Uiso calc R 1 1
C C8 0.13589(16) 0.33349(11) 0.48959(14) 0.0394(4) Uani d . 1 1
C C10 0.11093(15) 0.14936(10) 0.40823(14) 0.0381(4) Uani d . 1 1
C C1 0.24214(17) 0.29419(12) 0.96984(15) 0.0455(4) Uani d . 1 1
H H1A 0.3453 0.2980 0.9977 0.055 Uiso calc R 1 1
C C6 0.16472(15) 0.18558(11) 0.65030(14) 0.0380(4) Uani d . 1 1
C C12 0.0972(2) 0.48874(13) 0.33928(16) 0.0573(5) Uani d . 1 1
H H12A 0.1015 0.5671 0.3448 0.086 Uiso calc R 1 1
H H12B -0.0028 0.4662 0.2808 0.086 Uiso calc R 1 1
H H12C 0.1650 0.4629 0.3000 0.086 Uiso calc R 1 1
C C4 0.00631(16) 0.24161(13) 0.86324(15) 0.0475(4) Uani d . 1 1
H H4A -0.0788 0.2035 0.8059 0.057 Uiso calc R 1 1
C C2 0.15797(19) 0.36182(13) 1.01276(16) 0.0514(4) Uani d . 1 1
H H2A 0.1932 0.4197 1.0754 0.062 Uiso calc R 1 1
C C3 0.00937(18) 0.32851(14) 0.94572(16) 0.0528(4) Uani d . 1 1
H H3A -0.0726 0.3599 0.9556 0.063 Uiso calc R 1 1
C C13 0.0520(2) 0.10539(13) 0.16790(15) 0.0537(4) Uani d . 1 1
H H13A 0.0360 0.0427 0.1082 0.081 Uiso calc R 1 1
H H13B 0.1336 0.1478 0.1651 0.081 Uiso calc R 1 1
H H13C -0.0370 0.1493 0.1359 0.081 Uiso calc R 1 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
C4 N C1 108.58(13)
C4 N C5 125.56(13)
C1 N C5 125.05(13)
C8 O1 C12 118.35(12)
C10 O2 C13 117.65(11)
C6 C11 C10 120.26(12)
C6 C11 H11A 119.9
C10 C11 H11A 119.9
C6 C7 C8 120.00(13)
C6 C7 H7A 120.0
C8 C7 H7A 120.0
C8 C9 C10 117.98(12)
C8 C9 H9A 121.0
C10 C9 H9A 121.0
N C5 C6 113.71(12)
N C5 H5A 108.8
C6 C5 H5A 108.8
N C5 H5B 108.8
C6 C5 H5B 108.8
H5A C5 H5B 107.7
O1 C8 C7 115.00(13)
O1 C8 C9 123.69(13)
C7 C8 C9 121.31(13)
O2 C10 C11 115.85(12)
O2 C10 C9 123.04(12)
C11 C10 C9 121.11(13)
C2 C1 N 108.07(14)
C2 C1 H1A 126.0
N C1 H1A 126.0
C11 C6 C7 119.33(13)
C11 C6 C5 119.39(12)
C7 C6 C5 121.27(13)
O1 C12 H12A 109.5
O1 C12 H12B 109.5
H12A C12 H12B 109.5
O1 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
N C4 C3 108.38(13)
N C4 H4A 125.8
C3 C4 H4A 125.8
C1 C2 C3 107.53(15)
C1 C2 H2A 126.2
C3 C2 H2A 126.2
C4 C3 C2 107.42(14)
C4 C3 H3A 126.3
C2 C3 H3A 126.3
O2 C13 H13A 109.5
O2 C13 H13B 109.5
H13A C13 H13B 109.5
O2 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N C4 1.3589(19)
N C1 1.3631(18)
N C5 1.4568(18)
O1 C8 1.3652(16)
O1 C12 1.4207(17)
O2 C10 1.3693(16)
O2 C13 1.4284(17)
C11 C6 1.3849(19)
C11 C10 1.3845(19)
C11 H11A 0.9300
C7 C6 1.3883(19)
C7 C8 1.3868(19)
C7 H7A 0.9300
C9 C8 1.3880(19)
C9 C10 1.3934(19)
C9 H9A 0.9300
C5 C6 1.5097(19)
C5 H5A 0.9700
C5 H5B 0.9700
C1 C2 1.362(2)
C1 H1A 0.9300
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C4 C3 1.359(2)
C4 H4A 0.9300
C2 C3 1.393(2)
C2 H2A 0.9300
C3 H3A 0.9300
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 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
C1 H1A Cg 4_666 0.9300 2.79 3.6935(19) 165
C2 H2A O2 2_556 0.9300 2.715 3.527(2) 146.3
C5 H5A O2 3_556 0.9700 2.678 3.609(2) 160.9
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657710
