# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ocu_nosolvent
_database_code_depnum_ccdc_archive 'CCDC 2024768'
loop_
_audit_author_name
_audit_author_address
'Lina Zhou'
;Tianjin University
China
;
_audit_update_record             
;
2020-08-22 deposited with the CCDC.	2021-02-01 downloaded from the CCDC.
;
_audit_creation_date             2019-01-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        o-cresol_urea
_chemical_formula_moiety         'C H4 N2 O, C7 H8 O'
_chemical_formula_sum            'C8 H12 N2 O2'
_chemical_formula_weight         168.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   7.40010(10)
_cell_length_b                   26.1446(6)
_cell_length_c                   10.7253(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.9770(10)
_cell_angle_gamma                90
_cell_volume                     2070.06(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5457
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      76.1120
_cell_measurement_theta_min      3.3770
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.079
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20209
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.393
_diffrn_reflns_theta_min         3.381
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -119.00 -56.00   0.50    0.40    --  -46.50-159.00  47.00  126
  2  ω    -92.00 -16.00   0.50    0.40    --  -46.50 118.00 -73.00  152
  3  ω     50.00 120.00   0.50    0.40    --   46.50 159.00  79.00  140
  4  ω     10.00  92.00   0.50    0.40    --   46.50-118.00-159.00  164
  5  ω   -112.00 -27.00   0.50    1.60    -- -100.00 118.00 -73.00  170
  6  ω   -173.00 -84.00   0.50    1.60    -- -100.00-118.00-159.00  178
  7  ω     50.00 164.00   0.50    1.60    --  107.75 159.00  79.00  228
  8  ω     35.00 113.00   0.50    1.60    --  107.75-118.00-159.00  156
  9  ω     35.00 117.00   0.50    1.60    --  107.75-159.00  47.00  164
 10  ω    148.00 175.00   0.50    1.60    --  107.75 118.00 -73.00   54
 11  ω    -13.00  63.00   0.50    0.40    --   46.50 -57.00  60.00  152
 12  ω     31.00  64.00   0.50    0.40    --   46.50  57.00-150.00   66
 13  ω     89.00 117.00   0.50    0.40    --   46.50  57.00-150.00   56
 14  ω     73.00 120.00   0.50    0.40    --   46.50 125.00-120.00   94
 15  ω   -113.00 -52.00   0.50    1.60    -- -100.00  45.00 -30.00  122
 16  ω   -172.00 -87.00   0.50    1.60    -- -100.00 -45.00  30.00  170
 17  ω   -108.00 -49.00   0.50    1.60    -- -100.00  45.00 150.00  118
 18  ω     36.00  68.00   0.50    1.60    --  107.75 -61.00-180.00   64
 19  ω     36.00  89.00   0.50    1.60    --  107.75 -94.00 -30.00  106
 20  ω     68.00  94.00   0.50    1.60    --  107.75 -45.00 120.00   52
 21  ω     35.00  60.00   0.50    1.60    --  107.75 -45.00 120.00   50
 22  ω     98.00 172.00   0.50    1.60    --  107.75  30.00 -60.00  148
 23  ω     77.00 119.00   0.50    1.60    --  107.75 -61.00-180.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0219526000
_diffrn_orient_matrix_UB_12      -0.0260679000
_diffrn_orient_matrix_UB_13      0.1290636000
_diffrn_orient_matrix_UB_21      -0.0428507000
_diffrn_orient_matrix_UB_22      -0.0522090000
_diffrn_orient_matrix_UB_23      -0.0616910000
_diffrn_orient_matrix_UB_31      0.2029640000
_diffrn_orient_matrix_UB_32      -0.0082192000
_diffrn_orient_matrix_UB_33      -0.0167507000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2714
_reflns_number_total             4152
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.037
_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)+(0.1037P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1457
_refine_ls_wR_factor_ref         0.1652
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C10(H10), C8(H8), C11(H11), C9(H9), C5(H5), C3(H3), C4(H4A)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O2 O 0.39142(15) 0.78198(5) 0.49168(10) 0.0325(3) Uani 1 1 d . . . . .
O3 O 0.89065(15) 0.78151(5) 0.45258(10) 0.0331(3) Uani 1 1 d . . . . .
O1 O 0.36611(17) 0.68177(6) 0.55660(11) 0.0371(3) Uani 1 1 d . . . . .
O4 O 0.91398(18) 0.68132(6) 0.38851(11) 0.0393(3) Uani 1 1 d . . . . .
N2 N 0.7502(2) 0.80035(7) 0.62769(15) 0.0413(4) Uani 1 1 d . . . . .
N1 N 1.0580(2) 0.80414(8) 0.62856(16) 0.0435(4) Uani 1 1 d . . . . .
N3 N 0.5318(2) 0.80166(8) 0.31693(15) 0.0431(4) Uani 1 1 d . . . . .
N4 N 0.2233(2) 0.80499(8) 0.31670(15) 0.0434(4) Uani 1 1 d . . . . .
C13 C 0.3790(2) 0.59452(7) 0.49939(15) 0.0307(4) Uani 1 1 d . . . . .
C12 C 0.3846(2) 0.64566(7) 0.46484(15) 0.0300(4) Uani 1 1 d . . . . .
C1 C 0.8932(2) 0.64539(7) 0.47938(16) 0.0324(4) Uani 1 1 d . . . . .
C16 C 0.8993(2) 0.79526(7) 0.56612(15) 0.0312(4) Uani 1 1 d . . . . .
C15 C 0.3820(2) 0.79583(7) 0.37868(15) 0.0298(4) Uani 1 1 d . . . . .
C2 C 0.8740(2) 0.65901(8) 0.60309(16) 0.0356(4) Uani 1 1 d . . . . .
H2 H 0.875052 0.693337 0.625847 0.043 Uiso 1 1 calc R . . . .
C10 C 0.4244(2) 0.62227(8) 0.25173(15) 0.0363(4) Uani 1 1 d . . . . .
H10 H 0.438316 0.631524 0.169214 0.044 Uiso 1 1 calc R . . . .
C8 C 0.3984(2) 0.55805(7) 0.40744(17) 0.0354(4) Uani 1 1 d . . . . .
H8 H 0.396142 0.523608 0.428927 0.043 Uiso 1 1 calc R . . . .
C6 C 0.8913(2) 0.59419(8) 0.44333(17) 0.0352(4) Uani 1 1 d . . . . .
C11 C 0.4070(2) 0.65985(8) 0.34171(15) 0.0350(4) Uani 1 1 d . . . . .
H11 H 0.410267 0.694241 0.319865 0.042 Uiso 1 1 calc R . . . .
C9 C 0.4212(2) 0.57140(8) 0.28439(16) 0.0384(4) Uani 1 1 d . . . . .
H9 H 0.434224 0.546199 0.224480 0.046 Uiso 1 1 calc R . . . .
C5 C 0.8674(2) 0.55759(8) 0.53476(19) 0.0405(4) Uani 1 1 d . . . . .
H5 H 0.864025 0.523226 0.512284 0.049 Uiso 1 1 calc R . . . .
C14 C 0.3528(3) 0.57966(8) 0.63251(16) 0.0395(4) Uani 1 1 d . . . . .
H14A H 0.447214 0.594597 0.686699 0.059 Uiso 1 1 calc GR . . . .
H14B H 0.357309 0.543097 0.640265 0.059 Uiso 1 1 calc GR . . . .
H14C H 0.237328 0.591818 0.655480 0.059 Uiso 1 1 calc GR . . . .
C3 C 0.8534(2) 0.62157(8) 0.69274(17) 0.0397(4) Uani 1 1 d . . . . .
H3 H 0.842822 0.630751 0.775690 0.048 Uiso 1 1 calc R . . . .
C4 C 0.8486(3) 0.57073(8) 0.65850(19) 0.0437(5) Uani 1 1 d . . . . .
H4A H 0.832827 0.545478 0.717833 0.052 Uiso 1 1 calc R . . . .
C7 C 0.9154(3) 0.57925(9) 0.31017(18) 0.0446(5) Uani 1 1 d . . . . .
H7A H 0.910215 0.542691 0.302504 0.067 Uiso 1 1 calc GR . . . .
H7B H 1.030818 0.591227 0.286479 0.067 Uiso 1 1 calc GR . . . .
H7C H 0.820728 0.594304 0.256491 0.067 Uiso 1 1 calc GR . . . .
H3A H 0.638(3) 0.7970(9) 0.363(2) 0.050(6) Uiso 1 1 d . . . . .
H4B H 0.226(3) 0.8159(9) 0.235(2) 0.047(6) Uiso 1 1 d . . . . .
H2A H 0.640(3) 0.7944(8) 0.590(2) 0.042(6) Uiso 1 1 d . . . . .
H1A H 1.060(3) 0.8133(9) 0.708(3) 0.052(7) Uiso 1 1 d . . . . .
H4C H 0.118(3) 0.8004(9) 0.355(2) 0.050(6) Uiso 1 1 d . . . . .
H1B H 1.158(4) 0.7981(9) 0.592(2) 0.052(7) Uiso 1 1 d . . . . .
H1 H 0.376(4) 0.7139(12) 0.530(3) 0.070(9) Uiso 1 1 d . . . . .
H2B H 0.757(3) 0.8099(9) 0.711(2) 0.047(6) Uiso 1 1 d . . . . .
H4 H 0.905(4) 0.7141(12) 0.412(3) 0.076(9) Uiso 1 1 d . . . . .
H3B H 0.522(3) 0.8100(10) 0.233(2) 0.054(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C15 1.2622(19) . ?
O3 C16 1.267(2) . ?
O1 C12 1.377(2) . ?
O1 H1 0.89(3) . ?
O4 C1 1.370(2) . ?
O4 H4 0.90(3) . ?
N2 C16 1.331(2) . ?
N2 H2A 0.90(2) . ?
N2 H2B 0.93(3) . ?
N1 C16 1.332(2) . ?
N1 H1A 0.88(3) . ?
N1 H1B 0.87(3) . ?
N3 C15 1.339(2) . ?
N3 H3A 0.91(2) . ?
N3 H3B 0.92(3) . ?
N4 C15 1.331(2) . ?
N4 H4B 0.92(2) . ?
N4 H4C 0.91(3) . ?
C13 C12 1.389(3) . ?
C13 C8 1.386(3) . ?
C13 C14 1.505(2) . ?
C12 C11 1.393(2) . ?
C1 C2 1.390(2) . ?
C1 C6 1.393(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.389(3) . ?
C10 C9 1.376(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.387(3) . ?
C6 C5 1.390(3) . ?
C6 C7 1.503(3) . ?
C11 H11 0.9300 . ?
C9 H9 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.387(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C3 H3 0.9300 . ?
C3 C4 1.379(3) . ?
C4 H4A 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

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
_geom_angle_publ_flag
C12 O1 H1 113.5(18) . . ?
C1 O4 H4 116(2) . . ?
C16 N2 H2A 121.4(14) . . ?
C16 N2 H2B 120.8(14) . . ?
H2A N2 H2B 118(2) . . ?
C16 N1 H1A 119.0(16) . . ?
C16 N1 H1B 119.3(16) . . ?
H1A N1 H1B 121(2) . . ?
C15 N3 H3A 115.7(15) . . ?
C15 N3 H3B 119.6(15) . . ?
H3A N3 H3B 125(2) . . ?
C15 N4 H4B 116.8(14) . . ?
C15 N4 H4C 120.3(15) . . ?
H4B N4 H4C 123(2) . . ?
C12 C13 C14 120.66(16) . . ?
C8 C13 C12 117.76(15) . . ?
C8 C13 C14 121.59(17) . . ?
O1 C12 C13 117.57(15) . . ?
O1 C12 C11 121.28(17) . . ?
C13 C12 C11 121.15(16) . . ?
O4 C1 C2 121.82(17) . . ?
O4 C1 C6 117.44(16) . . ?
C2 C1 C6 120.74(17) . . ?
O3 C16 N2 121.13(15) . . ?
O3 C16 N1 121.11(16) . . ?
N2 C16 N1 117.75(16) . . ?
O2 C15 N3 121.02(14) . . ?
O2 C15 N4 121.29(15) . . ?
N4 C15 N3 117.70(15) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.26(19) . . ?
C3 C2 H2 119.9 . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.17(16) . . ?
C13 C8 H8 119.0 . . ?
C13 C8 C9 121.96(18) . . ?
C9 C8 H8 119.0 . . ?
C1 C6 C7 120.91(18) . . ?
C5 C6 C1 117.71(17) . . ?
C5 C6 C7 121.38(19) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 C12 119.55(18) . . ?
C10 C11 H11 120.2 . . ?
C10 C9 C8 119.41(17) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C6 C5 H5 119.0 . . ?
C4 C5 C6 122.03(19) . . ?
C4 C5 H5 119.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.83(18) . . ?
C4 C3 H3 120.1 . . ?
C5 C4 H4A 120.3 . . ?
C3 C4 C5 119.42(19) . . ?
C3 C4 H4A 120.3 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

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
_geom_torsion_publ_flag
O1 C12 C11 C10 -179.73(15) . . . . ?
O4 C1 C2 C3 -179.94(16) . . . . ?
O4 C1 C6 C5 -179.03(15) . . . . ?
O4 C1 C6 C7 1.3(2) . . . . ?
C13 C12 C11 C10 -0.1(2) . . . . ?
C13 C8 C9 C10 -0.1(3) . . . . ?
C12 C13 C8 C9 -0.6(2) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C1 C6 C5 C4 -0.9(3) . . . . ?
C2 C1 C6 C5 0.8(2) . . . . ?
C2 C1 C6 C7 -178.84(16) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C8 C13 C12 O1 -179.69(14) . . . . ?
C8 C13 C12 C11 0.7(2) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
C6 C5 C4 C3 0.0(3) . . . . ?
C11 C10 C9 C8 0.7(3) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C14 C13 C12 O1 0.2(2) . . . . ?
C14 C13 C12 C11 -179.38(15) . . . . ?
C14 C13 C8 C9 179.51(16) . . . . ?
C7 C6 C5 C4 178.70(17) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.099 0.000 0.500 227.8 60.7 ?
2 -0.613 0.500 0.000 227.8 60.7 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.437
_oxdiff_exptl_absorpt_empirical_full_min 0.839
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_pc_oxa_frxl
_database_code_depnum_ccdc_archive 'CCDC 2024770'
loop_
_audit_author_name
_audit_author_address
'Lina Zhou'
;Tianjin University
China
;
_audit_update_record             
;
2020-08-22 deposited with the CCDC.	2021-02-01 downloaded from the CCDC.
;
_audit_creation_date             2019-01-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'p-cresol_oxalic acid'
_chemical_formula_moiety         'C7 H8 O, C H O2'
_chemical_formula_sum            'C8 H9 O3'
_chemical_formula_weight         153.15
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   17.4483(6)
_cell_length_b                   6.0743(2)
_cell_length_c                   7.2533(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.229(3)
_cell_angle_gamma                90
_cell_volume                     764.21(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3567
_cell_measurement_temperature    160.00(10)
_cell_measurement_theta_max      74.5530
_cell_measurement_theta_min      2.5530
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.847
_exptl_absorpt_coefficient_mu    0.857
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6955
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.668
_diffrn_reflns_theta_min         2.547
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00  27.00   0.50    0.20    --  -45.62  75.00-119.00  190
  2  ω   -118.00 -23.00   0.50    0.20    --  -45.62 -75.00 113.00  190
  3  ω    -26.00  69.00   0.50    0.20    --   45.62 -75.00 113.00  190
  4  ω     23.00 119.00   0.50    0.20    --   45.62  75.00-119.00  192
  5  ω   -173.00 -77.00   0.50    0.80    -- -100.00 -75.00 113.00  192
  6  ω   -123.00 -27.00   0.50    0.80    -- -100.00  75.00-119.00  192
  7  ω     29.00 125.00   0.50    0.80    --  101.75 -75.00 113.00  192
  8  ω     79.00 175.00   0.50    0.80    --  101.75  75.00-119.00  192
  9  ω   -118.00 -73.00   0.50    0.20    --  -45.62-125.00 -90.00   90
 10  ω   -118.00 -73.00   0.50    0.20    --  -45.62-125.00-180.00   90
 11  ω   -175.00 -84.00   0.50    0.80    -- -100.00 -30.00  30.00  182
 12  ω   -172.00 -85.00   0.50    0.80    -- -100.00 -45.00 150.00  174
 13  ω   -118.00 -24.00   0.50    0.80    -- -100.00  15.00 -60.00  188
 14  ω     29.00 109.00   0.50    0.80    --  101.75 -94.00  30.00  160
 15  ω     29.00 109.00   0.50    0.80    --  101.75 -94.00 -30.00  160
 16  ω   -118.00 -29.00   0.50    0.20    --  -45.62 -57.00-180.00  178
 17  ω     22.00  59.00   0.50    0.20    --   45.62  77.00  30.00   74
 18  ω     30.00 119.00   0.50    0.20    --   45.62  57.00 -30.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0123867000
_diffrn_orient_matrix_UB_12      -0.2097433000
_diffrn_orient_matrix_UB_13      0.1189956000
_diffrn_orient_matrix_UB_21      -0.0846356000
_diffrn_orient_matrix_UB_22      0.0097980000
_diffrn_orient_matrix_UB_23      0.0418447000
_diffrn_orient_matrix_UB_31      -0.0239446000
_diffrn_orient_matrix_UB_32      -0.1421684000
_diffrn_orient_matrix_UB_33      -0.1724725000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1301
_reflns_number_total             1491
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0021(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1491
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0454
_refine_ls_restrained_S_all      1.054
_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)+(0.0444P)²+0.4207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1040
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H7BD)=Sof(H7BE)=Sof(H7BF)=1-FVAR(1)
 Sof(H7AA)=Sof(H7AB)=Sof(H7AC)=FVAR(1)
3.a Me refined with riding coordinates:
 C7(H7AA,H7AB,H7AC)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C1(H1A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O1 O 0.38740(6) 0.45083(17) 0.67107(15) 0.0250(3) Uani 1 1 d . . . . .
O2 O 0.47829(6) 0.72216(16) 0.51339(15) 0.0241(3) Uani 1 1 d . . . . .
O3 O 0.41990(6) 1.01541(16) 0.62478(15) 0.0243(3) Uani 1 1 d . . . . .
C8 C 0.46942(8) 0.9324(2) 0.54276(19) 0.0191(3) Uani 1 1 d . . . . .
C3 C 0.31067(8) 0.4722(2) 0.70246(19) 0.0206(3) Uani 1 1 d . . . . .
C2 C 0.25752(9) 0.3064(2) 0.6596(2) 0.0256(4) Uani 1 1 d . . . . .
H2 H 0.272372 0.175166 0.607886 0.031 Uiso 1 1 calc R . . . .
C4 C 0.28858(9) 0.6688(2) 0.7793(2) 0.0235(3) Uani 1 1 d . . . . .
H4 H 0.324433 0.780307 0.807637 0.028 Uiso 1 1 calc R . . . .
C6 C 0.15776(9) 0.5328(3) 0.7719(2) 0.0286(4) Uani 1 1 d . . . . .
C5 C 0.21255(9) 0.6968(3) 0.8131(2) 0.0258(4) Uani 1 1 d . . . . .
H5 H 0.197817 0.828302 0.864646 0.031 Uiso 1 1 calc R . . . .
C1 C 0.18173(9) 0.3382(3) 0.6946(2) 0.0298(4) Uani 1 1 d . . . . .
H1A H 0.145988 0.226462 0.665756 0.036 Uiso 1 1 calc R . . . .
C7 C 0.07529(11) 0.5648(4) 0.8116(3) 0.0449(5) Uani 1 1 d . . . . .
H7AA H 0.045848 0.435650 0.774481 0.067 Uiso 0.41(4) 1 calc R . P A 1
H7AB H 0.073938 0.589277 0.941966 0.067 Uiso 0.41(4) 1 calc R . P A 1
H7AC H 0.053655 0.689744 0.743588 0.067 Uiso 0.41(4) 1 calc R . P A 1
H1 H 0.3983(13) 0.312(4) 0.649(3) 0.053(7) Uiso 1 1 d . . . . .
H2A H 0.4404(13) 0.633(4) 0.564(3) 0.061(7) Uiso 1 1 d . . . . .
H7BD H 0.069(2) 0.719(7) 0.876(5) 0.051(12) Uiso 0.59(4) 1 d . . P A 2
H7BE H 0.058(2) 0.433(6) 0.885(5) 0.045(11) Uiso 0.59(4) 1 d . . P A 2
H7BF H 0.034(2) 0.554(6) 0.701(5) 0.044(11) Uiso 0.59(4) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.3881(17) . ?
O1 H1 0.88(3) . ?
O2 C8 1.3064(17) . ?
O2 H2A 0.96(3) . ?
O3 C8 1.2110(18) . ?
C8 C8 1.530(3) 3_676 ?
C3 C2 1.381(2) . ?
C3 C4 1.390(2) . ?
C2 H2 0.9300 . ?
C2 C1 1.387(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(2) . ?
C6 C5 1.390(2) . ?
C6 C1 1.392(2) . ?
C6 C7 1.510(2) . ?
C5 H5 0.9300 . ?
C1 H1A 0.9300 . ?
C7 H7AA 0.9600 . ?
C7 H7AB 0.9600 . ?
C7 H7AC 0.9600 . ?
C7 H7BD 1.06(4) . ?
C7 H7BE 1.03(4) . ?
C7 H7BF 1.02(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
_geom_angle_publ_flag
C3 O1 H1 110.4(15) . . ?
C8 O2 H2A 112.9(14) . . ?
O2 C8 C8 111.01(15) . 3_676 ?
O3 C8 O2 126.21(13) . . ?
O3 C8 C8 122.78(16) . 3_676 ?
O1 C3 C4 117.43(13) . . ?
C2 C3 O1 122.06(13) . . ?
C2 C3 C4 120.51(14) . . ?
C3 C2 H2 120.4 . . ?
C3 C2 C1 119.19(14) . . ?
C1 C2 H2 120.4 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.29(14) . . ?
C5 C4 H4 120.4 . . ?
C5 C6 C1 117.73(14) . . ?
C5 C6 C7 120.93(16) . . ?
C1 C6 C7 121.34(16) . . ?
C4 C5 C6 121.54(14) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C2 C1 C6 121.73(15) . . ?
C2 C1 H1A 119.1 . . ?
C6 C1 H1A 119.1 . . ?
C6 C7 H7AA 109.5 . . ?
C6 C7 H7AB 109.5 . . ?
C6 C7 H7AC 109.5 . . ?
C6 C7 H7BD 110(2) . . ?
C6 C7 H7BE 110.2(19) . . ?
C6 C7 H7BF 116.7(19) . . ?
H7AA C7 H7AB 109.5 . . ?
H7AA C7 H7AC 109.5 . . ?
H7AB C7 H7AC 109.5 . . ?
H7BD C7 H7BE 114(3) . . ?
H7BD C7 H7BF 108(3) . . ?
H7BE C7 H7BF 97(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.091
_oxdiff_exptl_absorpt_empirical_full_min 0.546
