#------------------------------------------------------------------------------
#$Date: 2019-11-24 07:01:33 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237044 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/42/1554234.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1554234
loop_
_publ_author_name
'Fang, Manman'
'Yang, Jie'
'Xiang, Xueqin'
'Xie, Yujun'
'Dong, Yongqiang'
'Peng, Qian'
'Li, Qianqian'
'Li, Zhen'
_publ_section_title
;
 Unexpected room-temperature phosphorescence from a non-aromatic, low
 molecular weight, pure organic molecule through the intermolecular
 hydrogen bond
;
_journal_issue                   11
_journal_name_full               'Materials Chemistry Frontiers'
_journal_page_first              2124
_journal_paper_doi               10.1039/C8QM00396C
_journal_volume                  2
_journal_year                    2018
_chemical_formula_moiety         'C3 H2 N2'
_chemical_formula_sum            'C3 H2 N2 O0'
_chemical_formula_weight         66.07
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-03-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-03-26 deposited with the CCDC.
2018-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 124.18(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.094(5)
_cell_length_b                   7.560(6)
_cell_length_c                   9.327(6)
_cell_measurement_reflns_used    862
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      22.88
_cell_measurement_theta_min      3.36
_cell_volume                     355.5(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2251
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.010
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         3.773
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_description       block
_exptl_crystal_F_000             136
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.214
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     46
_refine_ls_number_reflns         619
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.214
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0655
_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)+(0.0780P)²+0.1470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1843
_refine_ls_wR_factor_ref         0.1913
_reflns_Friedel_coverage         0.000
_reflns_number_gt                512
_reflns_number_total             619
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8qm00396c3.cif
_cod_data_source_block           MNN
_cod_database_code               1554234
_shelx_shelxl_version_number     2014/7
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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
N1 N 0.4387(7) 0.0143(5) 0.6871(3) 0.0931(12) Uani 1 1 d .
N2 N -0.0772(6) 0.1713(4) 0.1570(3) 0.0843(11) Uani 1 1 d .
C1 C 0.3649(6) 0.1229(4) 0.5897(4) 0.0627(9) Uani 1 1 d .
C2 C 0.2743(6) 0.2654(4) 0.4669(3) 0.0622(9) Uani 1 1 d .
H2A H 0.4238 0.3129 0.4689 0.075 Uiso 1 1 calc R
H2B H 0.2046 0.3591 0.5015 0.075 Uiso 1 1 calc R
C3 C 0.0725(5) 0.2113(3) 0.2931(3) 0.0518(8) Uani 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'
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
N1 C1 C2 178.7(4)
C1 C2 H2A 109.0
C1 C2 H2B 109.0
C1 C2 C3 112.8(3)
H2A C2 H2B 107.8
C3 C2 H2A 109.0
C3 C2 H2B 109.0
N2 C3 C2 177.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.115(4)
N2 C3 1.111(3)
C1 C2 1.438(4)
C2 H2A 0.9700
C2 H2B 0.9700
C2 C3 1.438(4)
