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#$Date: 2022-07-07 02:15:16 +0300 (Thu, 07 Jul 2022) $
#$Revision: 276715 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/72/1567248.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_1567248
loop_
_publ_author_name
'Morales-Collazo, Oscar'
'Lynch, Vincent M.'
'Brennecke, Joan F.'
_publ_section_title
;
 6,7-Dihydro-5H-pyrrolo[1,2-a]imidazole
;
_journal_coden_ASTM              IUCRBK
_journal_coeditor_code           WM4129
_journal_issue                   5
_journal_name_full               IUCrData
_journal_page_first              x200681
_journal_paper_doi               10.1107/s2414314620006811
_journal_volume                  5
_journal_year                    2020
_chemical_formula_iupac          'C6 H8 N2'
_chemical_formula_moiety         'C6 H8 N2'
_chemical_formula_sum            'C6 H8 N2'
_chemical_formula_weight         108.14
_chemical_name_systematic
;
6,7-Dihydro-5H-pyrrolo[1,2-a]imidazole
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2020-05-04 # Formatted by publCIF

2020-05-20 # Formatted by IUCr publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 104.91(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.908(7)
_cell_length_b                   7.441(8)
_cell_length_c                   9.880(9)
_cell_measurement_reflns_used    1451
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.66
_cell_volume                     561.8(9)
_computing_cell_refinement
;
CrystalClear (Rigaku, 2008)
;
_computing_data_collection
;
CrystalClear (Rigaku, 2008)
;
_computing_data_reduction
;
CrystalClear (Rigaku, 2008)
;
_computing_molecular_graphics
;
XP in SHELXTL/PC (Sheldrick, 2008) and MERCURY Macrae et al., 
2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku AFC-12 with Saturn 724+ CCD'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2575
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_min         2.955
_diffrn_source                   'sealed fine focus tube'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(ABSCOR; Higashi, 2001)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       prism
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     105
_refine_ls_number_reflns         1279
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0797P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1231
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1028
_reflns_number_total             1279
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm4129sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1567248
_publcif_datablock.id            {69de4aae-3b86-446c-ab32-2f5b6d445da7}
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.975
_shelx_estimated_absorpt_t_max   0.987
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
_publcif_funding_html
;
<span class="funder">
<span class="fundref-name" data-id="100000001">National Science
 Foundation</span>
<span class="fundref-subname" data-id=""></span> 
(<span class="fundref-grant-group"><span 
class="fundref-grant-type">grant</span> No. 
<span class="fundref-grant-id">0741973</span></span>).
</span>
;
loop_
_space_group_symop_operation_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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.35368(15) 0.73358(16) 0.04868(12) 0.0174(3) Uani 1 1 d . . . . .
C2 C 0.25317(16) 0.68855(17) -0.08171(12) 0.0197(3) Uani 1 1 d . . . . .
C3 C 0.20769(14) 0.96844(16) -0.05783(11) 0.0156(3) Uani 1 1 d . . . . .
C4 C 0.17443(17) 1.16552(17) -0.05457(13) 0.0209(3) Uani 1 1 d . . . . .
C5 C 0.26013(17) 1.21318(18) 0.10150(13) 0.0219(3) Uani 1 1 d . . . . .
C6 C 0.38632(16) 1.05792(16) 0.16201(12) 0.0183(3) Uani 1 1 d . . . . .
N1 N 0.32126(12) 0.91323(13) 0.06209(9) 0.0150(3) Uani 1 1 d . . . . .
N2 N 0.16179(13) 0.83657(14) -0.14934(10) 0.0194(3) Uani 1 1 d . . . . .
H1 H 0.4341(18) 0.6695(18) 0.1200(15) 0.024(4) Uiso 1 1 d . . . . .
H2 H 0.2433(17) 0.5700(17) -0.1276(14) 0.023(4) Uiso 1 1 d . . . . .
H4A H 0.2310(17) 1.2310(17) -0.1188(14) 0.023(4) Uiso 1 1 d . . . . .
H4B H 0.0496(19) 1.1952(19) -0.0828(15) 0.029(4) Uiso 1 1 d . . . . .
H5A H 0.3296(19) 1.333(2) 0.1160(16) 0.032(4) Uiso 1 1 d . . . . .
H5B H 0.167(2) 1.2194(19) 0.1527(15) 0.035(4) Uiso 1 1 d . . . . .
H6A H 0.5118(17) 1.0873(18) 0.1648(13) 0.022(3) Uiso 1 1 d . . . . .
H6B H 0.3805(18) 1.018(2) 0.2585(15) 0.036(4) Uiso 1 1 d . . . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 N1 104.54(10) . .
C2 C1 H1 133.8(8) . .
N1 C1 H1 121.6(8) . .
C1 C2 N2 111.23(12) . .
C1 C2 H2 127.5(8) . .
N2 C2 H2 121.2(8) . .
N2 C3 N1 112.18(12) . .
N2 C3 C4 136.59(11) . .
N1 C3 C4 111.13(10) . .
C3 C4 C5 102.18(10) . .
C3 C4 H4A 111.0(8) . .
C5 C4 H4A 111.6(8) . .
C3 C4 H4B 112.7(8) . .
C5 C4 H4B 112.4(8) . .
H4A C4 H4B 107.1(11) . .
C6 C5 C4 106.64(11) . .
C6 C5 H5A 108.9(8) . .
C4 C5 H5A 114.4(8) . .
C6 C5 H5B 109.0(8) . .
C4 C5 H5B 108.9(8) . .
H5A C5 H5B 108.9(12) . .
N1 C6 C5 102.10(11) . .
N1 C6 H6A 110.5(7) . .
C5 C6 H6A 112.4(8) . .
N1 C6 H6B 109.0(9) . .
C5 C6 H6B 113.8(9) . .
H6A C6 H6B 108.7(10) . .
C3 N1 C1 108.01(10) . .
C3 N1 C6 113.99(11) . .
C1 N1 C6 137.70(10) . .
C3 N2 C2 104.03(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3700(19) .
C1 N1 1.374(2) .
C1 H1 0.948(14) .
C2 N2 1.3905(18) .
C2 H2 0.986(13) .
C3 N2 1.3203(18) .
C3 N1 1.3533(17) .
C3 C4 1.492(2) .
C4 C5 1.557(2) .
C4 H4A 0.993(14) .
C4 H4B 0.980(15) .
C5 C6 1.543(2) .
C5 H5A 1.038(15) .
C5 H5B 0.994(15) .
C6 N1 1.4619(17) .
C6 H6A 1.010(13) .
C6 H6B 1.011(14) .
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
C1 H1 N2 0.95(1) 2.52(1) 3.73(3) 150(1)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N1 C3 C4 C5 -10.83(13) . . . .
C3 C4 C5 C6 18.49(13) . . . .
C4 C5 C6 N1 -19.28(13) . . . .
C4 C3 N1 C6 -1.63(13) . . . .
C5 C6 N1 C3 13.39(12) . . . .
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{69de4aae-3b86-446c-ab32-2f5b6d445da7} '_geom_hbond_atom_site_label_D'
{69de4aae-3b86-446c-ab32-2f5b6d445da7} '_publcif_info_datablock.publ_exptl'
loop_
_publcif_info_cif.paper_type
EX
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{69de4aae-3b86-446c-ab32-2f5b6d445da7} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

_cod_database_fobs_code 1567248
