#------------------------------------------------------------------------------
#$Date: 2019-11-24 07:01:33 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237044 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/42/1554235.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_1554235
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         'C2.98 H4 O4'
_chemical_formula_sum            'C3 H4 O4'
_chemical_formula_weight         104.06
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-03-24
_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                108.358(10)
_cell_angle_beta                 100.693(13)
_cell_angle_gamma                95.006(10)
_cell_formula_units_Z            2
_cell_length_a                   5.146(3)
_cell_length_b                   5.331(3)
_cell_length_c                   8.386(6)
_cell_measurement_reflns_used    52
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      7.5
_cell_volume                     211.9(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  bruker
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0119
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            1561
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.319
_diffrn_reflns_theta_min         2.627
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  0.9587
_exptl_absorpt_correction_T_min  0.9542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_description       block
_exptl_crystal_F_000             108
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1035
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0433
_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)+(0.0603P)²+0.0584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1166
_reflns_Friedel_coverage         0.000
_reflns_number_gt                918
_reflns_number_total             1035
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8qm00396c3.cif
_cod_data_source_block           MNA
_cod_database_code               1554235
_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. Restrained distances
 C3-O1
 1.3 with sigma of 0.01
 H2-O2
 0.929 with sigma of 0.01
3.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, -z'
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
C1 C 0.8022(3) 0.6529(2) 0.86257(16) 0.0293(4) Uani 0.985(7) 1 d .
C2 C 0.6291(3) 0.3938(3) 0.74653(19) 0.0368(3) Uani 1 1 d .
H2A H 0.5584 0.2991 0.8176 0.044 Uiso 1 1 calc R
H2B H 0.4751 0.4320 0.6725 0.044 Uiso 1 1 calc R
C3 C 0.7855(3) 0.2176(3) 0.63491(17) 0.0329(3) Uani 1 1 d D
O1 O 0.9143(3) 0.0648(3) 0.68435(17) 0.0593(4) Uani 1 1 d D
O2 O 0.7733(3) 0.2449(3) 0.48698(15) 0.0564(4) Uani 1 1 d D
O3 O 1.04392(19) 0.69165(19) 0.87263(14) 0.0388(3) Uani 1 1 d .
O4 O 0.6708(2) 0.8222(2) 0.94760(16) 0.0463(3) Uani 1 1 d .
H4 H 0.781(7) 0.976(7) 1.022(4) 0.103(10) Uiso 1 1 d .
H2 H 0.886(5) 0.144(5) 0.429(3) 0.096(9) Uiso 1 1 d 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'
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
O3 C1 C2 121.75(12)
O3 C1 O4 124.95(13)
O4 C1 C2 113.29(12)
C3 C2 C1 110.99(12)
O1 C3 C2 121.54(14)
O1 C3 O2 123.73(13)
O2 C3 C2 114.73(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.505(2)
C1 O3 1.2256(18)
C1 O4 1.2888(16)
C2 C3 1.5047(19)
C3 O1 1.2163(18)
C3 O2 1.284(2)
