# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_jcm016
_database_code_depnum_ccdc_archive 'CCDC 2046130'
loop_
_audit_author_name
_audit_author_address
'Kristof Van Hecke'
;Ghent University
Belgium
;
_audit_update_record             
;
2020-11-24 deposited with the CCDC.	2021-02-01 downloaded from the CCDC.
;
_audit_creation_date             2020-08-27
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H11 F3 N O2, Cl'
_chemical_formula_sum            'C10 H11 Cl F3 N O2'
_chemical_formula_weight         269.65
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H11 Cl F3 N O2'
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.6416(2)
_cell_length_b                   5.8788(2)
_cell_length_c                   18.0049(8)
_cell_angle_alpha                95.374(3)
_cell_angle_beta                 95.693(4)
_cell_angle_gamma                96.475(3)
_cell_volume                     587.08(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6177
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.5310
_cell_measurement_theta_min      4.9380
_shelx_estimated_absorpt_T_max   0.851
_shelx_estimated_absorpt_T_min   0.541
_exptl_absorpt_coefficient_mu    3.209
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.719
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             276
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 -1 1 0.0248
-4 1 -1 0.0263
-1 -4 2 0.1086
1 4 -2 0.0846
0 -1 12 0.0515
0 1 -12 0.0175
4 0 1 0.0281

_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.052
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.5728 -0.9717 0.9485 -0.0217 0.1213 -0.9924
-3.6029 0.7113 -0.8280 0.0089 -0.0526 0.9986
-0.6090 -3.6663 1.6718 -0.1812 0.9737 0.1381
0.6090 3.6663 -1.6718 0.1812 -0.9737 -0.1381
0.0213 -0.6123 11.6049 -0.9855 0.0254 -0.1681
-0.0213 0.6123 -11.6049 0.9855 -0.0254 0.1681
4.0006 0.0013 1.0008 -0.0106 -0.1523 -1.1088

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17106
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.328
_diffrn_reflns_theta_min         4.965
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    2.00    --  -41.68 -38.00  60.00   99
  2  ω   -116.00 -17.00   1.00    2.00    --  -41.68 -38.00 150.00   99
  3  ω     52.00 124.00   1.00    2.00    --   41.68-169.00  -0.00   72
  4  ω      7.00  33.00   1.00    2.00    --   41.68  84.00  32.23   26
  5  ω    -33.00  66.00   1.00    2.00    --   41.68 -38.00  30.00   99
  6  ω     14.00  42.00   1.00    2.00    --   46.00  76.00-119.46   28
  7  ω     16.00  42.00   1.00    2.00    --   50.00  81.00 -76.80   26
  8  ω     16.00  42.00   1.00    2.00    --   50.00  82.00 127.20   26
  9  ω     24.00 127.00   1.00    2.00    --   54.00  66.00 153.14  103
 10  ω     27.00 132.00   1.00    2.00    --   58.00  72.00 -61.61  105
 11  ω     30.00 137.00   1.00    2.00    --   62.00  73.00  73.57  107
 12  ω     31.00 136.00   1.00    2.00    --   62.00  72.00  -5.63  105
 13  ω     32.00 135.00   1.00    2.00    --   62.00  64.00-142.77  103
 14  ω     34.00 141.00   1.00    2.00    --   66.00  73.00  26.19  107
 15  ω     87.00 145.00   1.00    2.00    --   70.00  73.00-117.97   58
 16  ω     39.00 144.00   1.00    2.00    --   70.00  72.00 -36.07  105
 17  ω     42.00 142.00   1.00    2.00    --   70.00  55.00 173.30  100
 18  ω     54.00 154.00   1.00   12.00    --   82.00  55.00  21.42  100
 19  ω     50.00 157.00   1.00   12.00    --   82.00  74.00-162.36  107
 20  ω     63.00 168.00   1.00   12.00    --   94.00  71.00 140.39  105
 21  ω     87.00 167.00   1.00   12.00    --   94.00  69.00-110.46   80
 22  ω    103.00 167.00   1.00   12.00    --   94.00  66.00-154.40   64
 23  ω     23.00  83.00   1.00   12.00    --  106.01 -94.00   0.00   60
 24  ω     33.00  93.00   1.00   12.00    --  106.01-125.00 -60.00   60
 25  ω     77.00 178.00   1.00   12.00    --  106.01  61.00  90.00  101
 26  ω     30.00 100.00   1.00   12.00    --  106.01 -77.00  90.00   70
 27  ω     77.00 178.00   1.00   12.00    --  106.01  61.00 -90.00  101
 28  ω     33.00  93.00   1.00   12.00    --  106.01-125.00 -30.00   60
 29  ω     77.00 178.00   1.00   12.00    --  106.01  61.00 -30.00  101
 30  ω     77.00 178.00   1.00   12.00    --  106.01  61.00   0.00  101
 31  ω     33.00 112.00   1.00   12.00    --  106.01-125.00  90.00   79
 32  ω     77.00 178.00   1.00   12.00    --  106.01  61.00 120.00  101
 33  ω     77.00 178.00   1.00   12.00    --  106.01  61.00  30.00  101
 34  ω     77.00 178.00   1.00   12.00    --  106.01  61.00  60.00  101
 35  ω     77.00 178.00   1.00   12.00    --  106.01  61.00 -60.00  101
 36  ω     77.00 178.00   1.00   12.00    --  106.01  61.00-180.00  101
 37  ω     79.00 178.00   1.00   12.00    --  106.01  52.00-122.81   99
 38  ω    -46.00 130.00   1.00    2.00    --   41.68   0.00-150.00  176
 39  ω    -46.00 130.00   1.00    2.00    --   41.68   0.00 -60.00  176
 40  ω    -46.00 130.00   1.00    2.00    --   41.68   0.00 -90.00  176
 41  ω     27.00  98.00   1.00    2.00    --   41.68-125.00-180.00   71
 42  ω    -46.00 130.00   1.00    2.00    --   41.68   0.00 -30.00  176
 43  ω    -46.00 130.00   1.00    2.00    --   41.68   0.00-120.00  176
 44  ω    -46.00 130.00   1.00    2.00    --   41.68   0.00-180.00  176
 45  ω     61.00 160.00   1.00   12.00    --   86.00  40.00 178.35   99
 46  ω     80.00 178.00   1.00   12.00    --  106.01  45.00 120.00   98
 47  ω     18.00 153.00   1.00   12.00    --  106.01   0.00-180.00  135
 48  ω     77.00 178.00   1.00   12.00    --  106.01  61.00-150.00  101
 49  ω     34.00  84.00   1.00   12.00    --  106.01 -61.00-150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0184863000
_diffrn_orient_matrix_UB_12      0.0077966000
_diffrn_orient_matrix_UB_13      -0.0845396000
_diffrn_orient_matrix_UB_21      -0.0350475000
_diffrn_orient_matrix_UB_22      -0.2651110000
_diffrn_orient_matrix_UB_23      -0.0117361000
_diffrn_orient_matrix_UB_31      -0.2736768000
_diffrn_orient_matrix_UB_32      0.0014593000
_diffrn_orient_matrix_UB_33      -0.0139017000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1905
_reflns_number_total             2262
_reflns_odcompleteness_completeness 98.18
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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         0.808
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.098
_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     165
_refine_ls_number_reflns         2262
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0724
_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)+(0.0378P)²+4.2400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1829
_refine_ls_wR_factor_ref         0.1917
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9938(10)
 0.0062(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H,H) groups
3. Restrained distances
 O2-H2
 0.84 with sigma of 0.02
 N1-H1A = N1-H1B
 0.88 with sigma of 0.02
4.a Ternary CH refined with riding coordinates:
 C9(H9)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7)
4.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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
Cl1 Cl 0.2722(2) 0.0771(2) 0.59066(7) 0.0304(3) Uani 1 1 d . . . . .
F1 F 0.6917(7) 1.1009(7) 0.9450(2) 0.0612(12) Uani 1 1 d . . . . .
F2 F 0.7680(8) 0.7807(8) 0.9819(2) 0.0666(13) Uani 1 1 d . . . . .
F3 F 0.9265(6) 0.9057(7) 0.8884(2) 0.0514(10) Uani 1 1 d . . . . .
O1 O -0.1631(7) 0.2357(6) 0.7232(2) 0.0360(9) Uani 1 1 d . . . . .
O2 O -0.2516(7) 0.3587(6) 0.5088(2) 0.0333(8) Uani 1 1 d D . . . .
N1 N -0.2005(8) 0.2916(7) 0.5812(2) 0.0266(9) Uani 1 1 d D . . . .
C1 C 0.7240(10) 0.8840(10) 0.9208(3) 0.0367(13) Uani 1 1 d . . . . .
C2 C 0.5173(10) 0.7657(9) 0.8682(3) 0.0308(11) Uani 1 1 d . . . . .
C3 C 0.4000(11) 0.5549(9) 0.8818(3) 0.0353(12) Uani 1 1 d . . . . .
H3 H 0.447148 0.487113 0.925928 0.042 Uiso 1 1 calc R . . . .
C4 C 0.2147(10) 0.4453(9) 0.8306(3) 0.0340(12) Uani 1 1 d . . . . .
H4 H 0.133896 0.301766 0.839798 0.041 Uiso 1 1 calc R . . . .
C5 C 0.1445(9) 0.5428(8) 0.7653(3) 0.0292(11) Uani 1 1 d . . . . .
C6 C 0.2608(9) 0.7568(8) 0.7530(3) 0.0289(11) Uani 1 1 d . . . . .
H6 H 0.213488 0.825817 0.709161 0.035 Uiso 1 1 calc R . . . .
C7 C 0.4448(10) 0.8682(9) 0.8048(3) 0.0328(12) Uani 1 1 d . . . . .
H7 H 0.521482 1.015003 0.796960 0.039 Uiso 1 1 calc R . . . .
C8 C -0.0474(9) 0.4109(8) 0.7100(3) 0.0274(10) Uani 1 1 d . . . . .
C9 C -0.0994(9) 0.4971(8) 0.6333(3) 0.0254(10) Uani 1 1 d . . . . .
H9 H 0.054116 0.566038 0.616559 0.031 Uiso 1 1 calc R . . . .
C10 C -0.2765(10) 0.6739(9) 0.6340(3) 0.0354(12) Uani 1 1 d . . . . .
H10A H -0.293192 0.733648 0.584971 0.053 Uiso 1 1 calc GR . . . .
H10B H -0.217414 0.800856 0.672999 0.053 Uiso 1 1 calc GR . . . .
H10C H -0.432887 0.601154 0.644476 0.053 Uiso 1 1 calc GR . . . .
H2 H -0.253(13) 0.244(8) 0.477(3) 0.053 Uiso 1 1 d DR . . . .
H1A H -0.331(7) 0.212(10) 0.594(3) 0.043 Uiso 1 1 d DR . . . .
H1B H -0.087(8) 0.198(9) 0.584(4) 0.043 Uiso 1 1 d DR . . . .


_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
F1 C1 1.347(7) . ?
F2 C1 1.320(7) . ?
F3 C1 1.332(7) . ?
O1 C8 1.212(6) . ?
O2 N1 1.410(5) . ?
N1 C9 1.480(6) . ?
C1 C2 1.489(7) . ?
C2 C3 1.392(7) . ?
C2 C7 1.387(8) . ?
C3 C4 1.380(8) . ?
C4 C5 1.397(7) . ?
C5 C6 1.399(7) . ?
C5 C8 1.489(7) . ?
C6 C7 1.384(7) . ?
C8 C9 1.528(7) . ?
C9 C10 1.521(7) . ?

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
O2 N1 C9 109.1(4) . . ?
F1 C1 C2 112.2(5) . . ?
F2 C1 F1 105.9(5) . . ?
F2 C1 F3 107.1(5) . . ?
F2 C1 C2 114.1(5) . . ?
F3 C1 F1 104.8(5) . . ?
F3 C1 C2 112.1(5) . . ?
C3 C2 C1 120.7(5) . . ?
C7 C2 C1 118.8(5) . . ?
C7 C2 C3 120.5(5) . . ?
C4 C3 C2 119.4(5) . . ?
C3 C4 C5 120.8(5) . . ?
C4 C5 C6 119.1(5) . . ?
C4 C5 C8 118.5(4) . . ?
C6 C5 C8 122.3(5) . . ?
C7 C6 C5 120.1(5) . . ?
C6 C7 C2 120.0(5) . . ?
O1 C8 C5 122.4(5) . . ?
O1 C8 C9 118.5(5) . . ?
C5 C8 C9 119.0(4) . . ?
N1 C9 C8 106.0(4) . . ?
N1 C9 C10 109.9(4) . . ?
C10 C9 C8 112.5(4) . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a LithoLoop'
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.168
_oxdiff_exptl_absorpt_empirical_full_min 0.484
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9938(10)
2 0.0062(10)


####################################################################### 
# 
# 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_jcm017
_database_code_depnum_ccdc_archive 'CCDC 2046133'
loop_
_audit_author_name
_audit_author_address
'Kristof Van Hecke'
;Ghent University
Belgium
;
_audit_update_record             
;
2020-11-24 deposited with the CCDC.	2021-02-01 downloaded from the CCDC.
;
_audit_creation_date             2020-08-28
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H16 N O2, Cl'
_chemical_formula_sum            'C12 H16 Cl N O2'
_chemical_formula_weight         241.71
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H16 N O2, Cl'
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'
Cl Cl 0.1484 0.1585 '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'

_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                   6.09900(10)
_cell_length_b                   7.70410(10)
_cell_length_c                   25.2722(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.075(2)
_cell_angle_gamma                90
_cell_volume                     1184.47(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12930
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.5470
_cell_measurement_theta_min      3.2110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.250
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 3 -35 0.0968
0 -3 35 0.0968
6 -7 -10 0.0969
-6 7 10 0.0969
-5 -9 12 0.1033
5 9 -12 0.1033

_exptl_crystal_size_max          0.365
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.194
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.4282 2.6860 -34.5258 -0.8230 -0.5664 -0.0428
-0.4282 -2.6860 34.5258 0.8230 0.5664 0.0428
6.4421 -6.7668 -9.9217 -0.0491 -0.0322 -0.9983
-6.4421 6.7668 9.9217 0.0491 0.0322 0.9983
-4.7413 -8.5108 11.5495 0.9021 -0.4296 -0.0411
4.7413 8.5108 -11.5495 -0.9021 0.4296 0.0411

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            25529
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.648
_diffrn_reflns_theta_min         2.765
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  51.00   1.00   15.00    --   10.17 -99.00   0.00   66
  2  ω    -78.00  98.00   1.00   15.00    --   10.17   0.00  30.00  176
  3  ω    -31.00  90.00   1.00   15.00    --   10.17  19.00-150.00  121
  4  ω    -14.00  84.00   1.00   15.00    --   10.17  38.00  90.00   98
  5  ω    -44.00  21.00   1.00   15.00    --  -11.34  77.00 120.00   65
  6  ω    -15.00  30.00   1.00   15.00    --  -11.34 -99.00   0.00   45
  7  ω    -44.00  21.00   1.00   15.00    --  -11.34  77.00  30.00   65
  8  ω    -15.00  30.00   1.00   15.00    --  -11.34 -99.00-120.00   45
  9  ω    -44.00  21.00   1.00   15.00    --  -11.34  77.00-120.00   65
 10  ω    -15.00  17.00   1.00   15.00    --   10.17 -99.00-120.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0398580000
_diffrn_orient_matrix_UB_12      -0.0582628000
_diffrn_orient_matrix_UB_13      0.0188106000
_diffrn_orient_matrix_UB_21      0.0683952000
_diffrn_orient_matrix_UB_22      0.0400091000
_diffrn_orient_matrix_UB_23      0.0203663000
_diffrn_orient_matrix_UB_31      -0.0856403000
_diffrn_orient_matrix_UB_32      0.0590038000
_diffrn_orient_matrix_UB_33      0.0047676000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2758
_reflns_number_total             3178
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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         0.423
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3178
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0366P)²+0.5606P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0884
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H2A of C2, H5 of C5, H6 of C6, H3 of C3, All C(H,H,H)
  groups, All C(H,H,H,H) groups
 At 1.5 times of:
  H2 of C4
2. Restrained distances
 O2-H2
 0.84 with sigma of 0.02
 N1-H1A = N1-H1B
 0.88 with sigma of 0.02
3. Others
 Sof(H10C)=Sof(H10D)=Sof(H12D)=Sof(H12C)=Sof(C11B)=Sof(H11C)=Sof(H11D)=1-FVAR(1)
 Sof(H10A)=Sof(H10B)=Sof(H12B)=Sof(H12A)=Sof(C11A)=Sof(H11A)=Sof(H11B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10C,H10D), C10(H10A,H10B), C12(H12D,H12C), C12(H12B,H12A),
 C11A(H11A,H11B), C11B(H11C,H11D)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6)
;
_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
Cl1 Cl 0.27133(5) 0.39308(4) 0.54593(2) 0.02322(10) Uani 1 1 d . . . . .
O1 O 1.13884(15) 0.63023(14) 0.66228(4) 0.0262(2) Uani 1 1 d . . . . .
O2 O 0.72273(15) 0.41693(12) 0.59826(4) 0.0244(2) Uani 1 1 d D . . . .
N1 N 0.82971(17) 0.55931(14) 0.57574(4) 0.0194(2) Uani 1 1 d D . . . .
C1 C 0.83627(19) 0.66635(16) 0.71384(5) 0.0178(2) Uani 1 1 d . . . . .
C2 C 0.9576(2) 0.72814(17) 0.75910(5) 0.0231(3) Uani 1 1 d . . . . .
H2A H 1.101031 0.773763 0.756342 0.028 Uiso 1 1 calc R . . . .
C3 C 0.8678(3) 0.72253(18) 0.80790(5) 0.0281(3) Uani 1 1 d . . . . .
H3 H 0.948100 0.767221 0.838493 0.034 Uiso 1 1 calc R . . . .
C4 C 0.6609(3) 0.65179(19) 0.81212(5) 0.0287(3) Uani 1 1 d . . . . .
H4 H 0.600143 0.647694 0.845682 0.034 Uiso 1 1 calc R . . . .
H2 H 0.596(3) 0.410(2) 0.5811(7) 0.043 Uiso 1 1 d DR . . . .
H1A H 0.775(3) 0.577(2) 0.5412(6) 0.034 Uiso 1 1 d DR . . . .
H1B H 0.968(2) 0.523(2) 0.5718(7) 0.034 Uiso 1 1 d DR . . . .
C5 C 0.5421(2) 0.58691(18) 0.76762(5) 0.0245(3) Uani 1 1 d . . . . .
H5 H 0.401754 0.536198 0.770896 0.029 Uiso 1 1 calc R . . . .
C6 C 0.6282(2) 0.59603(16) 0.71832(5) 0.0194(2) Uani 1 1 d . . . . .
H6 H 0.545262 0.554365 0.687689 0.023 Uiso 1 1 calc R . . . .
C7 C 0.94558(19) 0.66693(16) 0.66304(5) 0.0182(2) Uani 1 1 d . . . . .
C8 C 0.82426(19) 0.71890(16) 0.60970(5) 0.0173(2) Uani 1 1 d . . . . .
C9 C 0.59014(19) 0.79066(17) 0.60938(5) 0.0193(2) Uani 1 1 d . . . . .
H9A H 0.480949 0.695442 0.606418 0.023 Uiso 1 1 calc R . . . .
H9B H 0.569779 0.857195 0.642185 0.023 Uiso 1 1 calc R . . . .
C10 C 0.5662(2) 0.90850(18) 0.56083(5) 0.0251(3) Uani 1 1 d . . . . .
H10C H 0.495884 0.843973 0.530289 0.030 Uiso 0.355(17) 1 calc R . P A 2
H10D H 0.472098 1.009146 0.568142 0.030 Uiso 0.355(17) 1 calc R . P A 2
H10A H 0.444699 0.992648 0.563276 0.030 Uiso 0.645(17) 1 calc R . P A 1
H10B H 0.542536 0.840872 0.527611 0.030 Uiso 0.645(17) 1 calc R . P A 1
C12 C 0.9577(2) 0.86014(19) 0.58220(6) 0.0256(3) Uani 1 1 d . . . . .
H12D H 1.038910 0.933772 0.609054 0.031 Uiso 0.355(17) 1 calc R . P A 2
H12C H 1.064782 0.805522 0.559703 0.031 Uiso 0.355(17) 1 calc R . P A 2
H12B H 1.074647 0.907787 0.607240 0.031 Uiso 0.645(17) 1 calc R . P A 1
H12A H 1.026523 0.810873 0.551226 0.031 Uiso 0.645(17) 1 calc R . P A 1
C11A C 0.7946(10) 1.0002(8) 0.5648(3) 0.0319(11) Uani 0.645(17) 1 d . . P A 1
H11A H 0.828211 1.048488 0.529970 0.038 Uiso 0.645(17) 1 calc R . P A 1
H11B H 0.797717 1.095589 0.591080 0.038 Uiso 0.645(17) 1 calc R . P A 1
C11B C 0.7904(19) 0.9705(15) 0.5479(4) 0.0255(16) Uani 0.355(17) 1 d . . P A 2
H11C H 0.808833 1.095227 0.556503 0.031 Uiso 0.355(17) 1 calc R . P A 2
H11D H 0.811051 0.953748 0.509721 0.031 Uiso 0.355(17) 1 calc R . 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 C7 1.2136(15) . ?
O2 N1 1.4161(14) . ?
N1 C8 1.5011(16) . ?
C1 C2 1.4009(17) . ?
C1 C6 1.3918(17) . ?
C1 C7 1.4882(16) . ?
C2 C3 1.3851(19) . ?
C3 C4 1.385(2) . ?
C4 C5 1.387(2) . ?
C5 C6 1.3878(18) . ?
C7 C8 1.5436(17) . ?
C8 C9 1.5307(16) . ?
C8 C12 1.5522(18) . ?
C9 C10 1.5249(17) . ?
C10 C11A 1.559(6) . ?
C10 C11B 1.506(12) . ?
C12 C11A 1.512(6) . ?
C12 C11B 1.546(11) . ?

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
O2 N1 C8 112.04(9) . . ?
C2 C1 C7 117.42(11) . . ?
C6 C1 C2 119.84(11) . . ?
C6 C1 C7 122.57(11) . . ?
C3 C2 C1 119.81(12) . . ?
C4 C3 C2 120.05(12) . . ?
C3 C4 C5 120.36(12) . . ?
C4 C5 C6 120.04(13) . . ?
C5 C6 C1 119.87(12) . . ?
O1 C7 C1 120.54(11) . . ?
O1 C7 C8 116.91(11) . . ?
C1 C7 C8 122.53(10) . . ?
N1 C8 C7 104.95(9) . . ?
N1 C8 C9 110.57(10) . . ?
N1 C8 C12 106.53(10) . . ?
C7 C8 C12 109.80(10) . . ?
C9 C8 C7 119.18(10) . . ?
C9 C8 C12 105.24(10) . . ?
C10 C9 C8 104.78(10) . . ?
C9 C10 C11A 100.6(3) . . ?
C11B C10 C9 109.1(4) . . ?
C11A C12 C8 106.0(3) . . ?
C11B C12 C8 106.9(4) . . ?
C12 C11A C10 105.2(3) . . ?
C10 C11B C12 106.1(6) . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a LithoLoop'
_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 1.317
_oxdiff_exptl_absorpt_empirical_full_min 0.801

####################################################################### 
# 
# 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_jcm012
_database_code_depnum_ccdc_archive 'CCDC 2046131'
loop_
_audit_author_name
_audit_author_address
'Kristof Van Hecke'
;Ghent University
Belgium
;
_audit_update_record             
;
2020-11-24 deposited with the CCDC.	2021-02-01 downloaded from the CCDC.
;
_audit_creation_date             2019-08-06
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H13 N O2'
_chemical_formula_sum            'C10 H13 N O2'
_chemical_formula_weight         179.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H13 N O2'
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                   5.7769(3)
_cell_length_b                   7.6286(5)
_cell_length_c                   21.5338(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.167(5)
_cell_angle_gamma                90
_cell_volume                     943.50(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3037
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      74.9950
_cell_measurement_theta_min      4.1050
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.716
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.708
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             384
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -14 0.0192
0 0 14 0.0617
2 -1 9 0.0748
-3 2 -3 0.1073
0 5 1 0.0457
0 -5 -1 0.0010
3 -2 -5 0.1049
-4 0 5 0.1291

_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.047
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0961 -0.2196 -13.9129 0.6847 -0.6483 0.3331
0.0867 0.1265 13.8494 -0.6963 0.6594 -0.2834
2.4496 -1.1266 9.0532 -0.6490 0.6158 0.4467
-3.3645 1.6678 -2.6416 0.4040 -0.3843 -0.8301
0.0366 4.9353 1.0731 0.6400 0.6748 -0.3676
-0.0366 -4.9353 -1.0731 -0.6400 -0.6748 0.3676
2.9520 -1.7206 -5.3681 0.0051 -0.0455 0.9099
-3.8926 -0.3758 5.4958 -0.2980 -0.3447 -0.9771

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9351
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.308
_diffrn_reflns_theta_min         4.130
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    6.00    --  -41.68 -38.00  90.00   99
  2  ω   -115.00 -14.00   1.00    6.00    --  -41.68 -57.00-120.00  101
  3  ω    -92.00  -2.00   1.00    6.00    --  -41.68 125.00  30.00   90
  4  ω   -116.00 -17.00   1.00    6.00    --  -41.68 -38.00   0.00   99
  5  ω    -34.00  74.00   1.00    6.00    --   41.68 -77.00 -60.00  108
  6  ω     27.00  87.00   1.00   30.00    --  109.13 -96.00 -12.00   60
  7  ω     94.00 178.00   1.00   30.00    --  109.13 125.00-120.00   84
  8  ω     36.00 117.00   1.00   30.00    --  109.13-125.00-150.00   81
  9  ω     87.00 178.00   1.00   30.00    --  109.13  45.00 150.00   91
 10  ω     36.00  81.00   1.00   30.00    --  109.13-125.00 120.00   45
 11  ω     81.00 178.00   1.00   30.00    --  109.13  30.00  30.00   97
 12  ω     33.00 137.00   1.00   30.00    --  109.13 -30.00  60.00  104
 13  ω     36.00  66.00   1.00   30.00    --  109.13-125.00 -30.00   30
 14  ω     81.00 178.00   1.00   30.00    --  109.13  30.00-150.00   97
 15  ω     33.00  53.00   1.00   30.00    --  109.13 -30.00-150.00   20
 16  ω     36.00  61.00   1.00   30.00    --  109.13 -45.00 -30.00   25
 17  ω   -115.00 -14.00   1.00    6.00    --  -41.68 -57.00 -30.00  101
 18  ω     68.00 118.00   1.00    6.00    --   41.68  77.00-180.00   50
 19  ω     98.00 118.00   1.00    6.00    --   41.68  77.00  90.00   20
 20  ω      1.00  71.00   1.00    6.00    --   41.68 -99.00-150.00   70
 21  ω     83.00 178.00   1.00   30.00    --  109.13  45.00  90.00   95
 22  ω    111.00 178.00   1.00   30.00    --  109.13  77.00  90.00   67
 23  ω     81.00 178.00   1.00   30.00    --  109.13  30.00 -60.00   97
 24  ω    111.00 178.00   1.00   30.00    --  109.13  77.00  30.00   67
 25  ω    107.00 178.00   1.00   30.00    --  109.13  45.00-120.00   71
 26  ω    129.00 178.00   1.00   30.00    --  109.13  61.00 -30.00   49
 27  ω    144.00 178.00   1.00   30.00    --  109.13  61.00 -60.00   34
 28  ω    126.00 178.00   1.00   30.00    --  109.13  77.00-180.00   52
 29  ω    129.00 178.00   1.00   30.00    --  109.13  61.00-120.00   49
 30  ω     36.00  81.00   1.00   30.00    --  109.13-125.00 -90.00   45
 31  ω     38.00  69.00   1.00    6.00    --   41.68  77.00   0.00   31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0097755000
_diffrn_orient_matrix_UB_12      0.1409510000
_diffrn_orient_matrix_UB_13      -0.0515029000
_diffrn_orient_matrix_UB_21      0.1407785000
_diffrn_orient_matrix_UB_22      0.1257671000
_diffrn_orient_matrix_UB_23      0.0455849000
_diffrn_orient_matrix_UB_31      0.2279319000
_diffrn_orient_matrix_UB_32      -0.0715472000
_diffrn_orient_matrix_UB_33      -0.0212359000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1435
_reflns_number_total             1859
_reflns_odcompleteness_completeness 98.58
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         0.206
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1859
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.056
_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)+(0.0640P)²+0.1570P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1245
_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, All C(H,H,H,H) groups
2. Restrained distances
 O2-H2
 0.84 with sigma of 0.01
 N1-H1
 0.88 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
3.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_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 0.6213(2) 0.66812(18) 0.62404(5) 0.0345(3) Uani 1 1 d . . . . .
O2 O 0.1382(2) 0.44694(16) 0.56637(5) 0.0301(3) Uani 1 1 d D . . . .
N1 N 0.0545(2) 0.6252(2) 0.55660(6) 0.0275(3) Uani 1 1 d D . . . .
C1 C 0.4154(3) 0.6891(2) 0.62874(7) 0.0229(4) Uani 1 1 d . . . . .
C2 C 0.3301(3) 0.6785(2) 0.69183(7) 0.0217(3) Uani 1 1 d . . . . .
C3 C 0.1246(3) 0.5977(2) 0.70468(7) 0.0232(3) Uani 1 1 d . . . . .
H3 H 0.027489 0.542524 0.672008 0.028 Uiso 1 1 calc R . . . .
C4 C 0.0608(3) 0.5975(2) 0.76510(7) 0.0260(4) Uani 1 1 d . . . . .
H4 H -0.079451 0.541844 0.773641 0.031 Uiso 1 1 calc R . . . .
C5 C 0.2018(3) 0.6785(2) 0.81300(7) 0.0281(4) Uani 1 1 d . . . . .
H5 H 0.156211 0.680239 0.854093 0.034 Uiso 1 1 calc R . . . .
C6 C 0.4082(3) 0.7566(2) 0.80100(7) 0.0288(4) Uani 1 1 d . . . . .
H6 H 0.505567 0.810184 0.833995 0.035 Uiso 1 1 calc R . . . .
C7 C 0.4735(3) 0.7569(2) 0.74095(7) 0.0256(4) Uani 1 1 d . . . . .
H7 H 0.615807 0.810294 0.732936 0.031 Uiso 1 1 calc R . . . .
C8 C 0.2508(3) 0.7465(2) 0.57065(7) 0.0241(4) Uani 1 1 d . . . . .
C9 C 0.3857(3) 0.7580(2) 0.51377(7) 0.0291(4) Uani 1 1 d . . . . .
H9A H 0.440749 0.640962 0.503638 0.044 Uiso 1 1 calc GR . . . .
H9B H 0.519313 0.836411 0.522927 0.044 Uiso 1 1 calc GR . . . .
H9C H 0.283741 0.803862 0.478160 0.044 Uiso 1 1 calc GR . . . .
C10 C 0.1468(4) 0.9239(2) 0.58546(8) 0.0367(5) Uani 1 1 d . . . . .
H10A H 0.039715 0.962827 0.549729 0.055 Uiso 1 1 calc GR . . . .
H10B H 0.272125 1.010084 0.593847 0.055 Uiso 1 1 calc GR . . . .
H10C H 0.061948 0.912698 0.622290 0.055 Uiso 1 1 calc GR . . . .
H2 H 0.094(4) 0.405(3) 0.5303(7) 0.055 Uiso 1 1 d DR . . . .
H1 H -0.053(3) 0.636(3) 0.5830(9) 0.044 Uiso 1 1 d DR . . . .


_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 C1 1.215(2) . ?
O2 N1 1.4510(19) . ?
N1 C8 1.470(2) . ?
C1 C2 1.496(2) . ?
C1 C8 1.5510(19) . ?
C2 C3 1.391(2) . ?
C2 C7 1.405(2) . ?
C3 C4 1.390(2) . ?
C4 C5 1.389(2) . ?
C5 C6 1.382(3) . ?
C6 C7 1.385(2) . ?
C8 C9 1.523(2) . ?
C8 C10 1.528(2) . ?

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
O2 N1 C8 108.84(12) . . ?
O1 C1 C2 119.29(13) . . ?
O1 C1 C8 119.40(14) . . ?
C2 C1 C8 120.96(14) . . ?
C3 C2 C1 125.17(13) . . ?
C3 C2 C7 119.03(14) . . ?
C7 C2 C1 115.80(14) . . ?
C4 C3 C2 120.31(14) . . ?
C5 C4 C3 120.09(16) . . ?
C6 C5 C4 120.12(15) . . ?
C5 C6 C7 120.13(14) . . ?
C6 C7 C2 120.30(16) . . ?
N1 C8 C1 112.39(13) . . ?
N1 C8 C9 108.70(12) . . ?
N1 C8 C10 106.80(14) . . ?
C9 C8 C1 110.02(13) . . ?
C9 C8 C10 111.32(14) . . ?
C10 C8 C1 107.60(12) . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_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 2.254
_oxdiff_exptl_absorpt_empirical_full_min 0.210


####################################################################### 
# 
# 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_jcm003
_database_code_depnum_ccdc_archive 'CCDC 2046135'
loop_
_audit_author_name
_audit_author_address
'Kristof Van Hecke'
;Ghent University
Belgium
;
_audit_update_record             
;
2020-11-24 deposited with the CCDC.	2021-02-01 downloaded from the CCDC.
;
_audit_creation_date             2018-05-23
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5497)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C8 H8 N2 O2'
_chemical_formula_sum            'C8 H8 N2 O2'
_chemical_formula_weight         164.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H8 N2 O2'
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.9356(3)
_cell_length_b                   3.81317(10)
_cell_length_c                   21.6720(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.7022(19)
_cell_angle_gamma                90
_cell_volume                     1532.30(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    14698
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      74.6410
_cell_measurement_theta_min      4.1480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.876
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 2 -2 0.0745
7 -1 -13 0.1392
1 -2 1 0.1044
-7 1 12 0.0279
-10 1 -4 0.0565
-12 0 -1 0.0553
11 0 2 0.0180
10 -1 4 0.0339

_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.085
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0031 1.9998 -2.0010 0.3841 -0.3284 0.6561
7.0002 -1.0003 -12.9952 -0.8272 0.5683 0.4029
1.0028 -1.9998 1.0014 -0.4395 0.3205 -0.6099
-7.0005 1.0002 11.9955 0.7719 -0.5763 -0.3566
-10.0073 0.9994 -3.9986 -0.1778 -0.9410 0.3452
-12.0064 -0.0005 -0.9986 -0.3129 -0.9591 -0.1074
11.0062 0.0005 1.9983 0.3468 0.8878 0.0483
10.0073 -0.9994 3.9986 0.1778 0.9410 -0.3452

_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            38369
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.275
_diffrn_reflns_theta_min         4.166
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00-180.00  100
  2  ω    -74.00  34.00   1.00    1.00    --  -41.80  77.00  90.00  108
  3  ω   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00  90.00  100
  4  ω   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00 -30.00  100
  5  ω    -34.00  74.00   1.00    1.00    --   41.80 -77.00-180.00  108
  6  ω     23.00  98.00   1.00    1.00    --   41.80-125.00  60.00   75
  7  ω      5.00  32.00   1.00    1.00    --   42.00  90.00  98.07   27
  8  ω     11.00  38.00   1.00    1.00    --   46.00  84.00 176.00   27
  9  ω     12.00  40.00   1.00    1.00    --   46.00  83.00 -75.64   28
 10  ω     17.00  45.00   1.00    1.00    --   50.00  80.00-149.23   28
 11  ω     16.00  45.00   1.00    1.00    --   50.00  81.00 112.39   29
 12  ω     16.00  45.00   1.00    1.00    --   50.00  81.00   2.03   29
 13  ω     33.00 142.00   1.00    1.00    --   66.00  77.00  39.37  109
 14  ω     34.00 141.00   1.00    1.00    --   66.00  75.00 169.00  107
 15  ω     34.00 142.00   1.00    1.00    --   66.00  76.00 -85.20  108
 16  ω     34.00 142.00   1.00    1.00    --   66.00  76.00 -55.27  108
 17  ω     37.00 146.00   1.00    1.00    --   70.00  77.00-123.20  109
 18  ω     38.00 146.00   1.00    1.00    --   70.00  76.00  68.89  108
 19  ω     37.00 146.00   1.00    1.00    --   70.00  77.00 131.98  109
 20  ω     42.00 150.00   1.00    1.00    --   74.00  76.00-179.27  108
 21  ω     42.00 149.00   1.00    1.00    --   74.00  75.00 -57.94  107
 22  ω     41.00 150.00   1.00    1.00    --   74.00  77.00 -29.52  109
 23  ω     41.00 150.00   1.00    1.00    --   74.00  77.00   0.21  109
 24  ω     41.00 150.00   1.00    1.00    --   74.00  77.00-152.61  109
 25  ω     47.00 152.00   1.00    1.00    --   78.00  71.00  95.87  105
 26  ω     51.00 156.00   1.00    1.00    --   82.00  71.00  73.73  105
 27  ω     54.00 162.00   1.00    1.00    --   86.00  76.00-107.65  108
 28  ω     59.00 164.00   1.00    1.00    --   90.00  71.00 113.00  105
 29  ω     59.00 164.00   1.00    1.00    --   90.00  72.00   1.09  105
 30  ω     60.00 163.00   1.00    1.00    --   90.00  65.00-142.90  103
 31  ω     65.00 166.00   1.00    1.00    --   94.00  61.00 -17.07  101
 32  ω     67.00 172.00   1.00    1.00    --   98.00  70.00 168.73  105
 33  ω     36.00 117.00   1.00    1.00    --  109.13-125.00-120.00   81
 34  ω     77.00 178.00   1.00    1.00    --  109.13  77.00 120.00  101
 35  ω     80.00 178.00   1.00    1.00    --  109.13  61.00  90.00   98
 36  ω     26.00 110.00   1.00    1.00    --  109.13 -94.00 -30.00   84
 37  ω     33.00 142.00   1.00    1.00    --  109.13 -77.00  60.00  109
 38  ω     77.00 178.00   1.00    1.00    --  109.13  77.00  60.00  101
 39  ω     36.00 117.00   1.00    1.00    --  109.13-125.00 -60.00   81
 40  ω     77.00 178.00   1.00    1.00    --  109.13  77.00  30.00  101
 41  ω     80.00 178.00   1.00    1.00    --  109.13  61.00 -90.00   98
 42  ω     77.00 178.00   1.00    1.00    --  109.13  77.00-180.00  101
 43  ω     83.00 178.00   1.00    1.00    --  109.13  45.00 -30.00   95
 44  ω     77.00 178.00   1.00    1.00    --  109.13  77.00 -90.00  101
 45  ω     77.00 178.00   1.00    1.00    --  109.13  77.00-150.00  101
 46  ω     77.00 178.00   1.00    1.00    --  109.13  77.00   0.00  101
 47  ω     26.00 110.00   1.00    1.00    --  109.13 -94.00  30.00   84
 48  ω     82.00 178.00   1.00    1.00    --  110.00  55.00-107.29   96
 49  ω     17.00 116.00   1.00    1.00    --   41.80  38.00 120.00   99
 50  ω     16.00 115.00   1.00    1.00    --   41.80  43.00  25.80   99
 51  ω      1.00 122.00   1.00    1.00    --   41.80  19.00   0.00  121
 52  ω      7.00  36.00   1.00    1.00    --   42.00  85.00 -86.03   29
 53  ω     11.00  38.00   1.00    1.00    --   46.00  84.00-131.82   27
 54  ω     11.00  38.00   1.00    1.00    --   46.00  84.00  95.57   27
 55  ω     30.00 138.00   1.00    1.00    --   62.00  76.00  87.47  108
 56  ω     30.00 137.00   1.00    1.00    --   62.00  75.00  -3.45  107
 57  ω     29.00 138.00   1.00    1.00    --   62.00  77.00-162.14  109
 58  ω     35.00 140.00   1.00    1.00    --   66.00  72.00  29.25  105
 59  ω     34.00 141.00   1.00    1.00    --   66.00  75.00 107.96  107
 60  ω     38.00 146.00   1.00    1.00    --   70.00  76.00 -46.99  108
 61  ω     38.00 146.00   1.00    1.00    --   70.00  76.00-159.25  108
 62  ω     38.00 145.00   1.00    1.00    --   70.00  75.00 124.67  107
 63  ω     43.00 147.00   1.00    1.00    --   74.00  69.00 -74.31  104
 64  ω     51.00 150.00   1.00    1.00    --   78.00  52.00  69.38   99
 65  ω     48.00 151.00   1.00    1.00    --   78.00  67.00-141.95  103
 66  ω     52.00 155.00   1.00    1.00    --   82.00  65.00  72.36  103
 67  ω     21.00 178.00   1.00    1.00    --  109.13   0.00-150.00  157
 68  ω     21.00 178.00   1.00    1.00    --  109.13   0.00-180.00  157
 69  ω     80.00 178.00   1.00    1.00    --  109.13  61.00-150.00   98
 70  ω     36.00 117.00   1.00    1.00    --  109.13-125.00 -30.00   81
 71  ω     77.00 178.00   1.00    1.00    --  109.13  77.00  90.00  101
 72  ω     77.00 178.00   1.00    1.00    --  109.13  77.00-120.00  101
 73  ω     80.00 178.00   1.00    1.00    --  109.13  61.00  60.00   98
 74  ω     80.00 178.00   1.00    1.00    --  109.13  61.00 -30.00   98
 75  ω     83.00 178.00   1.00    1.00    --  109.13  45.00  30.00   95
 76  ω     36.00 117.00   1.00    1.00    --  109.13-125.00-150.00   81
 77  ω     21.00  94.00   1.00    1.00    --  109.13   0.00   0.00   73
 78  ω     80.00 178.00   1.00    1.00    --  109.13  61.00 150.00   98
 79  ω     21.00 178.00   1.00    1.00    --  109.13   0.00 -30.00  157
 80  ω     21.00 178.00   1.00    1.00    --  109.13   0.00 -60.00  157
 81  ω     80.00 178.00   1.00    1.00    --  109.13  61.00 120.00   98
 82  ω     21.00 178.00   1.00    1.00    --  109.13   0.00 -90.00  157
 83  ω     21.00 178.00   1.00    1.00    --  109.13   0.00-120.00  157
 84  ω     80.00 178.00   1.00    1.00    --  109.13  61.00  30.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0214467000
_diffrn_orient_matrix_UB_12      0.2582056000
_diffrn_orient_matrix_UB_13      0.0553363000
_diffrn_orient_matrix_UB_21      0.0792303000
_diffrn_orient_matrix_UB_22      -0.1165705000
_diffrn_orient_matrix_UB_23      0.0079177000
_diffrn_orient_matrix_UB_31      0.0127838000
_diffrn_orient_matrix_UB_32      0.2881895000
_diffrn_orient_matrix_UB_33      -0.0463009000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1386
_reflns_number_total             1577
_reflns_odcompleteness_completeness 99.94
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         1577
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.043
_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)+(0.0578P)²+1.2741P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1050
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.56583(4) 0.0283(3) 0.46114(4) 0.0272(3) Uani 1 1 d . . . . .
H1 H 0.5661 -0.0490 0.4975 0.041 Uiso 1 1 calc GR . . . .
O2 O 0.42177(5) 0.3972(3) 0.27929(4) 0.0340(3) Uani 1 1 d . . . . .
N1 N 0.49435(5) 0.1148(3) 0.43139(5) 0.0231(3) Uani 1 1 d . . . . .
N2 N 0.55296(6) 0.2971(4) 0.35094(6) 0.0306(3) Uani 1 1 d . . . . .
C1 C 0.49430(7) 0.2429(4) 0.37610(6) 0.0230(3) Uani 1 1 d . . . . .
C2 C 0.42287(7) 0.3303(4) 0.33458(6) 0.0236(3) Uani 1 1 d . . . . .
C3 C 0.35531(7) 0.3236(4) 0.35955(6) 0.0214(3) Uani 1 1 d . . . . .
C4 C 0.35172(7) 0.4496(4) 0.41914(6) 0.0230(3) Uani 1 1 d . . . . .
H4 H 0.3937 0.5386 0.4462 0.028 Uiso 1 1 calc R . . . .
C5 C 0.28664(7) 0.4443(4) 0.43879(6) 0.0265(3) Uani 1 1 d . . . . .
H5 H 0.2840 0.5311 0.4794 0.032 Uiso 1 1 calc R . . . .
C6 C 0.22506(7) 0.3131(4) 0.39961(7) 0.0289(3) Uani 1 1 d . . . . .
H6 H 0.1808 0.3061 0.4138 0.035 Uiso 1 1 calc R . . . .
H2A H 0.5468(9) 0.343(5) 0.3104(9) 0.035 Uiso 1 1 d R . . . .
H2B H 0.5933(9) 0.201(5) 0.3722(8) 0.035 Uiso 1 1 d R . . . .
C7 C 0.22813(7) 0.1920(4) 0.33980(7) 0.0282(3) Uani 1 1 d . . . . .
H7 H 0.1859 0.1040 0.3129 0.034 Uiso 1 1 calc R . . . .
C8 C 0.29297(7) 0.1999(4) 0.31956(6) 0.0240(3) Uani 1 1 d . . . . .
H8 H 0.2951 0.1209 0.2784 0.029 Uiso 1 1 calc R . . . .


_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 N1 1.4151(13) . ?
O2 C2 1.2211(16) . ?
N1 C1 1.2937(17) . ?
N2 C1 1.3490(16) . ?
C1 C2 1.5021(17) . ?
C2 C3 1.4870(17) . ?
C3 C4 1.3923(18) . ?
C3 C8 1.3971(18) . ?
C4 C5 1.3831(18) . ?
C5 C6 1.389(2) . ?
C6 C7 1.388(2) . ?
C7 C8 1.3854(18) . ?

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
C1 N1 O1 109.33(10) . . ?
N1 C1 N2 125.89(12) . . ?
N1 C1 C2 118.04(11) . . ?
N2 C1 C2 116.04(11) . . ?
O2 C2 C1 117.92(11) . . ?
O2 C2 C3 121.07(11) . . ?
C3 C2 C1 120.98(11) . . ?
C4 C3 C2 122.62(12) . . ?
C4 C3 C8 119.85(12) . . ?
C8 C3 C2 117.46(11) . . ?
C5 C4 C3 119.65(12) . . ?
C4 C5 C6 120.45(12) . . ?
C7 C6 C5 120.12(12) . . ?
C8 C7 C6 119.73(12) . . ?
C7 C8 C3 120.17(12) . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_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 1.601
_oxdiff_exptl_absorpt_empirical_full_min 0.667

####################################################################### 
# 
# 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_jcm009
_database_code_depnum_ccdc_archive 'CCDC 2046134'
loop_
_audit_author_name
_audit_author_address
'Kristof Van Hecke'
;Ghent University
Belgium
;
_audit_update_record             
;
2020-11-24 deposited with the CCDC.	2021-02-01 downloaded from the CCDC.
;
_audit_creation_date             2019-05-24
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H14 Cl N O2'
_chemical_formula_sum            'C12 H14 Cl N O2'
_chemical_formula_weight         239.69
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H14 Cl N O2'
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'
Cl Cl 0.3639 0.7018 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.7548(3)
_cell_length_b                   10.5744(5)
_cell_length_c                   10.5916(6)
_cell_angle_alpha                110.243(5)
_cell_angle_beta                 102.912(5)
_cell_angle_gamma                100.879(5)
_cell_volume                     563.94(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5211
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      75.0080
_cell_measurement_theta_min      4.6240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.876
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             252
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -7 1 0.0803
0 7 -1 0.0653
-3 4 -1 0.0209
3 -4 1 0.1024
0 -1 6 0.0378
0 1 -6 0.0148
2 2 -7 0.0689
3 0 1 0.0990

_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.053
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0032 -6.5028 1.4981 -0.8860 0.1284 -0.4031
-0.0032 6.5028 -1.4981 0.8860 -0.1284 0.4031
-3.0006 4.0021 -0.9970 0.6987 -0.1309 -0.6013
3.0006 -4.0021 0.9970 -0.6987 0.1309 0.6013
-0.0031 -0.5064 6.4995 0.1393 0.9781 0.2920
0.0031 0.5064 -6.4995 -0.1393 -0.9781 -0.2920
2.0016 1.5064 -6.5004 -0.0995 -0.9360 0.3453
2.9975 0.4983 1.4983 -0.0354 0.2754 0.9582

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10603
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.488
_diffrn_reflns_theta_min         4.658
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00-180.00  100
  2  ω    -66.00  32.00   1.00    1.00    --  -41.80  38.00 -30.00   98
  3  ω      1.00  83.00   1.00    1.00    --   41.80 -99.00 -30.00   82
  4  ω    -34.00  74.00   1.00    1.00    --   41.80 -77.00  60.00  108
  5  ω     36.00 117.00   1.00    4.00    --  109.13-125.00 150.00   81
  6  ω     94.00 178.00   1.00    4.00    --  109.13 125.00  30.00   84
  7  ω     94.00 178.00   1.00    4.00    --  109.13 125.00  90.00   84
  8  ω     98.00 178.00   1.00    4.00    --  109.13  86.00-114.00   80
  9  ω     81.00 178.00   1.00    4.00    --  109.13  30.00 150.00   97
 10  ω     36.00 117.00   1.00    4.00    --  109.13-125.00 -30.00   81
 11  ω     83.00 178.00   1.00    4.00    --  109.13  45.00-150.00   95
 12  ω     37.00 138.00   1.00    4.00    --  109.13 -61.00 120.00  101
 13  ω     36.00 117.00   1.00    4.00    --  109.13-125.00  60.00   81
 14  ω     36.00 135.00   1.00    4.00    --  109.13 -45.00 -30.00   99
 15  ω   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00  90.00  100
 16  ω   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00   0.00  100
 17  ω   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00 -90.00  100
 18  ω    -32.00  66.00   1.00    1.00    --   41.80 -38.00 120.00   98
 19  ω     80.00 178.00   1.00    4.00    --  109.13  61.00 150.00   98
 20  ω     80.00 178.00   1.00    4.00    --  109.13  61.00 -90.00   98
 21  ω     83.00 178.00   1.00    4.00    --  109.13  45.00  60.00   95
 22  ω     83.00 178.00   1.00    4.00    --  109.13  45.00-120.00   95
 23  ω     81.00 178.00   1.00    4.00    --  109.13  30.00   0.00   97
 24  ω     77.00 178.00   1.00    4.00    --  109.13  77.00   0.00  101
 25  ω     80.00 178.00   1.00    4.00    --  109.13  61.00 -60.00   98
 26  ω     83.00 178.00   1.00    4.00    --  109.13  45.00  90.00   95
 27  ω   -118.00  -9.00   1.00    1.00    --  -41.80 -77.00-120.00  109
 28  ω   -118.00  -9.00   1.00    1.00    --  -41.80 -77.00  60.00  109
 29  ω   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00 -60.00  100
 30  ω     23.00  98.00   1.00    1.00    --   41.80-125.00-180.00   75
 31  ω     80.00 178.00   1.00    4.00    --  109.13  61.00-180.00   98
 32  ω     80.00 158.00   1.00    4.00    --  109.13  61.00-120.00   78
 33  ω     77.00 178.00   1.00    4.00    --  109.13  77.00 -30.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0520011000
_diffrn_orient_matrix_UB_12      0.1437265000
_diffrn_orient_matrix_UB_13      0.0325973000
_diffrn_orient_matrix_UB_21      0.0135280000
_diffrn_orient_matrix_UB_22      0.0152090000
_diffrn_orient_matrix_UB_23      0.1516758000
_diffrn_orient_matrix_UB_31      0.2819856000
_diffrn_orient_matrix_UB_32      0.0738384000
_diffrn_orient_matrix_UB_33      0.0508150000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2051
_reflns_number_total             2285
_reflns_odcompleteness_completeness 100.00
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0568P)²+0.1413P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1015
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C10A) = Uanis(C10B)
Uanis(C11A) = Uanis(C11B)
3. Others
 Sof(H9BC)=Sof(H9BD)=Sof(H12C)=Sof(H12D)=Sof(C10B)=Sof(H10C)=Sof(H10D)=
 Sof(C11B)=Sof(H11C)=Sof(H11D)=1-FVAR(1)
 Sof(H9AA)=Sof(H9AB)=Sof(H12A)=Sof(H12B)=Sof(C10A)=Sof(H10A)=Sof(H10B)=
 Sof(C11A)=Sof(H11A)=Sof(H11B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C9(H9AA,H9AB), C9(H9BC,H9BD), C12(H12A,H12B), C12(H12C,H12D), C10A(H10A,H10B),
  C11A(H11A,H11B), C10B(H10C,H10D), C11B(H11C,H11D)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Cl1 Cl 1.03025(8) 0.06878(4) 0.20181(4) 0.02295(14) Uani 1 1 d . . . . .
O1 O 1.1702(2) 0.33049(13) 0.48801(12) 0.0229(3) Uani 1 1 d . . . . .
O2 O 0.6095(3) 0.02563(12) 0.38117(12) 0.0244(3) Uani 1 1 d . . . . .
H2 H 0.562(5) -0.044(3) 0.408(3) 0.037 Uiso 1 1 d R . . . .
N1 N 0.5771(3) 0.14533(13) 0.48808(14) 0.0184(3) Uani 1 1 d . . . . .
C1 C 0.8280(3) 0.16978(16) 0.18759(16) 0.0181(3) Uani 1 1 d . . . . .
C2 C 0.6995(3) 0.15527(18) 0.05380(17) 0.0225(4) Uani 1 1 d . . . . .
H2A H 0.727786 0.094377 -0.027598 0.027 Uiso 1 1 calc R . . . .
C3 C 0.5293(3) 0.23029(19) 0.03951(17) 0.0239(4) Uani 1 1 d . . . . .
H3 H 0.443219 0.222334 -0.051843 0.029 Uiso 1 1 calc R . . . .
C4 C 0.4842(3) 0.31708(18) 0.15836(18) 0.0235(4) Uani 1 1 d . . . . .
H4 H 0.365480 0.367213 0.148116 0.028 Uiso 1 1 calc R . . . .
C5 C 0.6132(3) 0.33048(16) 0.29259(17) 0.0191(3) Uani 1 1 d . . . . .
H5 H 0.581306 0.389442 0.373638 0.023 Uiso 1 1 calc R . . . .
C6 C 0.7883(3) 0.25819(16) 0.30879(15) 0.0165(3) Uani 1 1 d . . . . .
C7 C 0.9453(3) 0.28258(15) 0.45419(15) 0.0159(3) Uani 1 1 d . . . . .
C8 C 0.8205(3) 0.25409(16) 0.55910(15) 0.0160(3) Uani 1 1 d . . . . .
C9 C 0.7748(3) 0.39048(16) 0.65554(16) 0.0177(3) Uani 1 1 d . . . . .
H9AA H 0.851359 0.472118 0.637798 0.021 Uiso 0.792(7) 1 calc R . P A 1
H9AB H 0.593967 0.379148 0.635943 0.021 Uiso 0.792(7) 1 calc R . P A 1
H9BC H 0.606384 0.396636 0.616124 0.021 Uiso 0.208(7) 1 calc R . P A 2
H9BD H 0.901500 0.476437 0.670651 0.021 Uiso 0.208(7) 1 calc R . P A 2
C12 C 0.9906(3) 0.21188(18) 0.66230(17) 0.0223(4) Uani 1 1 d . . . . .
H12A H 1.168617 0.255022 0.677966 0.027 Uiso 0.792(7) 1 calc R . P A 1
H12B H 0.956058 0.108260 0.626141 0.027 Uiso 0.792(7) 1 calc R . P A 1
H12C H 0.914420 0.113107 0.645772 0.027 Uiso 0.208(7) 1 calc R . P A 2
H12D H 1.154150 0.218726 0.645545 0.027 Uiso 0.208(7) 1 calc R . P A 2
C10A C 0.8946(7) 0.4132(4) 0.8088(3) 0.0290(7) Uani 0.792(7) 1 d . . P A 1
H10A H 1.059238 0.485222 0.850616 0.035 Uiso 0.792(7) 1 calc R . P A 1
H10B H 0.787013 0.444038 0.867222 0.035 Uiso 0.792(7) 1 calc R . P A 1
C11A C 0.9220(7) 0.2704(3) 0.8000(2) 0.0231(6) Uani 0.792(7) 1 d . . P A 1
H11A H 0.764037 0.208392 0.793929 0.028 Uiso 0.792(7) 1 calc R . P A 1
H11B H 1.055590 0.280572 0.883277 0.028 Uiso 0.792(7) 1 calc R . P A 1
C10B C 0.802(3) 0.3657(14) 0.7949(12) 0.0290(7) Uani 0.208(7) 1 d . . P A 2
H10C H 0.836965 0.455323 0.877481 0.035 Uiso 0.208(7) 1 calc R . P A 2
H10D H 0.649540 0.298318 0.787232 0.035 Uiso 0.208(7) 1 calc R . P A 2
C11B C 1.025(3) 0.3047(13) 0.8078(11) 0.0231(6) Uani 0.208(7) 1 d . . P A 2
H11C H 1.185252 0.380366 0.848057 0.028 Uiso 0.208(7) 1 calc R . P A 2
H11D H 1.021917 0.251418 0.868382 0.028 Uiso 0.208(7) 1 calc R . P A 2
H1 H 0.466(4) 0.174(2) 0.437(2) 0.028 Uiso 1 1 d R . . . .


_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
Cl1 C1 1.7381(16) . ?
O1 C7 1.216(2) . ?
O2 N1 1.4527(16) . ?
N1 C8 1.474(2) . ?
C1 C2 1.384(2) . ?
C1 C6 1.398(2) . ?
C2 C3 1.386(2) . ?
C3 C4 1.390(2) . ?
C4 C5 1.394(2) . ?
C5 C6 1.390(2) . ?
C6 C7 1.507(2) . ?
C7 C8 1.532(2) . ?
C8 C9 1.5608(19) . ?
C8 C12 1.542(2) . ?
C9 C10A 1.528(3) . ?
C9 C10B 1.565(12) . ?
C12 C11A 1.547(3) . ?
C12 C11B 1.456(11) . ?
C10A C11A 1.521(4) . ?
C10B C11B 1.542(19) . ?

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
O2 N1 C8 107.65(12) . . ?
C2 C1 Cl1 118.48(12) . . ?
C2 C1 C6 121.24(15) . . ?
C6 C1 Cl1 120.21(12) . . ?
C1 C2 C3 119.49(15) . . ?
C2 C3 C4 120.23(14) . . ?
C3 C4 C5 119.91(15) . . ?
C6 C5 C4 120.49(14) . . ?
C1 C6 C7 120.54(14) . . ?
C5 C6 C1 118.62(14) . . ?
C5 C6 C7 120.69(13) . . ?
O1 C7 C6 118.79(14) . . ?
O1 C7 C8 121.10(13) . . ?
C6 C7 C8 120.04(13) . . ?
N1 C8 C7 112.70(12) . . ?
N1 C8 C9 107.12(13) . . ?
N1 C8 C12 109.54(13) . . ?
C7 C8 C9 110.84(12) . . ?
C7 C8 C12 111.33(13) . . ?
C12 C8 C9 104.93(12) . . ?
C8 C9 C10B 100.4(5) . . ?
C10A C9 C8 106.85(14) . . ?
C8 C12 C11A 103.40(15) . . ?
C11B C12 C8 109.8(4) . . ?
C11A C10A C9 104.9(2) . . ?
C10A C11A C12 103.3(2) . . ?
C11B C10B C9 103.7(9) . . ?
C12 C11B C10B 103.6(9) . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_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 3.218
_oxdiff_exptl_absorpt_empirical_full_min 0.449

####################################################################### 
# 
# 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_jcm010
_database_code_depnum_ccdc_archive 'CCDC 2046132'
loop_
_audit_author_name
_audit_author_address
'Kristof Van Hecke'
;Ghent University
Belgium
;
_audit_update_record             
;
2020-11-24 deposited with the CCDC.	2021-02-01 downloaded from the CCDC.
;
_audit_creation_date             2019-06-14
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H13 N O2'
_chemical_formula_sum            'C11 H13 N O2'
_chemical_formula_weight         191.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H13 N O2'
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                   9.0379(3)
_cell_length_b                   10.0440(3)
_cell_length_c                   11.0835(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.123(3)
_cell_angle_gamma                90
_cell_volume                     993.40(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4897
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      75.0820
_cell_measurement_theta_min      4.9080
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.716
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.857
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 -1 1 0.0311
-1 2 7 0.0470
0 3 -7 0.1201
-5 0 -3 0.0480
-6 -2 1 0.0267
0 -3 7 0.0464
5 1 2 0.0441
5 2 -3 0.0941
4 -3 -4 0.0446
-4 3 4 0.0446
4 3 4 0.0396
-4 -3 -4 0.0391
-2 6 0 0.0850
2 -6 0 0.0405

_exptl_crystal_size_max          0.191
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.079
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
5.0013 -0.9998 0.9999 0.3390 -0.0789 0.8399
-1.0052 2.0005 6.9922 -0.9034 0.1071 0.4612
-0.0006 3.0039 -6.9940 0.6480 0.6218 -0.6129
-4.9994 -0.0009 -2.9975 -0.0896 -0.0212 -1.0146
-5.9988 -2.0036 0.9991 -0.5323 -0.4383 -0.8148
0.0006 -3.0039 6.9940 -0.6480 -0.6218 0.6129
4.9986 1.0019 1.9982 0.1624 0.1955 0.9269
4.9995 2.0036 -2.9972 0.6648 0.4687 0.4894
4.0054 -3.0011 -3.9946 0.8629 -0.2736 0.2528
-4.0054 3.0011 3.9946 -0.8629 0.2736 -0.2528
3.9955 3.0032 3.9954 -0.2040 0.4262 0.9509
-3.9955 -3.0032 -3.9954 0.2040 -0.4262 -0.9509
-2.0070 6.0050 -0.0023 -0.3724 0.8593 -0.3024
2.0070 -6.0050 0.0023 0.3724 -0.8593 0.3024

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18075
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.607
_diffrn_reflns_theta_min         4.956
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  32.00   1.00    2.00    --  -41.80  38.00   0.00   98
  2  ω    -66.00  32.00   1.00    2.00    --  -41.80  38.00 -90.00   98
  3  ω     23.00  98.00   1.00    2.00    --   41.80-125.00  90.00   75
  4  ω     14.00 115.00   1.00    2.00    --   41.80  57.00 -90.00  101
  5  ω      1.00  83.00   1.00    2.00    --   41.80 -99.00 -90.00   82
  6  ω    -30.00  70.00   1.00    2.00    --   41.80 -57.00  30.00  100
  7  ω     33.00 137.00   1.00    6.00    --  109.13 -30.00 120.00  104
  8  ω     36.00 117.00   1.00    6.00    --  109.13-125.00 120.00   81
  9  ω     36.00 135.00   1.00    6.00    --  109.13 -45.00-150.00   99
 10  ω     83.00 178.00   1.00    6.00    --  109.13  45.00  60.00   95
 11  ω     94.00 178.00   1.00    6.00    --  109.13 125.00 -90.00   84
 12  ω     36.00 135.00   1.00    6.00    --  109.13 -45.00  30.00   99
 13  ω     33.00 142.00   1.00    6.00    --  109.13 -77.00-120.00  109
 14  ω     33.00 142.00   1.00    6.00    --  109.13 -77.00   0.00  109
 15  ω     37.00 123.00   1.00    6.00    --  109.13-133.00-113.00   86
 16  ω     28.00 162.00   1.00    6.00    --  109.13 -15.00 -60.00  134
 17  ω     14.00 115.00   1.00    2.00    --   41.80  57.00 150.00  101
 18  ω     14.00 115.00   1.00    2.00    --   41.80  57.00-150.00  101
 19  ω     14.00 115.00   1.00    2.00    --   41.80  57.00  30.00  101
 20  ω      9.00 118.00   1.00    2.00    --   41.80  77.00 -60.00  109
 21  ω     77.00 178.00   1.00    6.00    --  109.13  77.00 150.00  101
 22  ω     56.00 178.00   1.00    6.00    --  109.13  15.00 -60.00  122
 23  ω     81.00 178.00   1.00    6.00    --  109.13  30.00   0.00   97
 24  ω     79.00 178.00   1.00    6.00    --  109.13  68.00  77.00   99
 25  ω     56.00 178.00   1.00    6.00    --  109.13  15.00-180.00  122
 26  ω     83.00 178.00   1.00    6.00    --  109.13  45.00 -60.00   95
 27  ω     83.00 178.00   1.00    6.00    --  109.13  45.00  30.00   95
 28  ω     77.00 178.00   1.00    6.00    --  109.13  77.00-180.00  101
 29  ω      1.00  83.00   1.00    2.00    --   41.80 -99.00-180.00   82
 30  ω      9.00 118.00   1.00    2.00    --   41.80  77.00-180.00  109
 31  ω      9.00 118.00   1.00    2.00    --   41.80  77.00  60.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0823683000
_diffrn_orient_matrix_UB_12      -0.0345238000
_diffrn_orient_matrix_UB_13      -0.1074844000
_diffrn_orient_matrix_UB_21      0.0190360000
_diffrn_orient_matrix_UB_22      0.1494519000
_diffrn_orient_matrix_UB_23      -0.0247110000
_diffrn_orient_matrix_UB_31      0.1504254000
_diffrn_orient_matrix_UB_32      -0.0000449000
_diffrn_orient_matrix_UB_33      0.0875947000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1589
_reflns_number_total             2033
_reflns_odcompleteness_completeness 100.00
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         2033
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.055
_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)+(0.0554P)²+0.2815P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1220
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H9 of C9, H11 of C11, H8 of C8, H10 of C10, H7 of C7,
  All C(H,H,H) groups
 At 1.5 times of:
  H1 of C3
2. Restrained distances
 O1-H1
 0.84 with sigma of 0.01
 N1-H1A
 0.88 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.35769(15) 0.02437(11) 0.89478(11) 0.0284(3) Uani 1 1 d D . . . .
O2 O 0.36491(14) 0.18212(11) 0.64694(10) 0.0289(3) Uani 1 1 d . . . . .
N1 N 0.44233(16) 0.13877(12) 0.94909(12) 0.0226(3) Uani 1 1 d D . . . .
C1 C 0.48999(18) 0.21623(14) 0.84940(14) 0.0202(3) Uani 1 1 d . . . . .
C2 C 0.63431(19) 0.15758(16) 0.81469(16) 0.0281(4) Uani 1 1 d . . . . .
H2A H 0.643879 0.170550 0.727718 0.034 Uiso 1 1 calc R . . . .
H2B H 0.651711 0.063378 0.839173 0.034 Uiso 1 1 calc R . . . .
C3 C 0.7267(2) 0.25739(17) 0.90193(18) 0.0320(4) Uani 1 1 d . . . . .
H3A H 0.770433 0.218522 0.981720 0.038 Uiso 1 1 calc R . . . .
H3B H 0.803525 0.305789 0.864685 0.038 Uiso 1 1 calc R . . . .
H1 H 0.409(2) -0.0402(18) 0.930(2) 0.048 Uiso 1 1 d DR . . . .
H1A H 0.375(2) 0.1860(19) 0.9820(18) 0.038 Uiso 1 1 d DR . . . .
C4 C 0.58260(19) 0.33849(15) 0.90573(15) 0.0249(4) Uani 1 1 d . . . . .
H4A H 0.572897 0.418030 0.852305 0.030 Uiso 1 1 calc R . . . .
H4B H 0.565657 0.361408 0.989335 0.030 Uiso 1 1 calc R . . . .
C5 C 0.36155(19) 0.23858(14) 0.74435(14) 0.0206(3) Uani 1 1 d . . . . .
C6 C 0.23408(18) 0.32870(14) 0.75797(14) 0.0210(3) Uani 1 1 d . . . . .
C7 C 0.22810(19) 0.40206(14) 0.86449(15) 0.0225(3) Uani 1 1 d . . . . .
H7 H 0.305258 0.392536 0.932888 0.027 Uiso 1 1 calc R . . . .
C8 C 0.1098(2) 0.48867(16) 0.87051(16) 0.0284(4) Uani 1 1 d . . . . .
H8 H 0.106010 0.538099 0.943041 0.034 Uiso 1 1 calc R . . . .
C9 C -0.0030(2) 0.50314(17) 0.77077(19) 0.0336(4) Uani 1 1 d . . . . .
H9 H -0.084130 0.562096 0.775228 0.040 Uiso 1 1 calc R . . . .
C10 C 0.0026(2) 0.43155(17) 0.66445(18) 0.0331(4) Uani 1 1 d . . . . .
H10 H -0.074253 0.442140 0.596010 0.040 Uiso 1 1 calc R . . . .
C11 C 0.1198(2) 0.34498(15) 0.65799(16) 0.0261(4) Uani 1 1 d . . . . .
H11 H 0.122912 0.296067 0.585061 0.031 Uiso 1 1 calc R . . . .


_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 N1 1.4566(17) . ?
O2 C5 1.2241(19) . ?
N1 C1 1.4706(18) . ?
C1 C2 1.535(2) . ?
C1 C4 1.560(2) . ?
C1 C5 1.525(2) . ?
C2 C3 1.543(2) . ?
C3 C4 1.542(2) . ?
C5 C6 1.491(2) . ?
C6 C7 1.400(2) . ?
C6 C11 1.399(2) . ?
C7 C8 1.388(2) . ?
C8 C9 1.387(3) . ?
C9 C10 1.388(3) . ?
C10 C11 1.381(2) . ?

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
O1 N1 C1 107.70(11) . . ?
N1 C1 C2 110.31(13) . . ?
N1 C1 C4 108.56(12) . . ?
N1 C1 C5 111.93(13) . . ?
C2 C1 C4 88.80(12) . . ?
C5 C1 C2 116.07(13) . . ?
C5 C1 C4 119.01(12) . . ?
C1 C2 C3 89.45(12) . . ?
C4 C3 C2 89.14(13) . . ?
C3 C4 C1 88.57(12) . . ?
O2 C5 C1 118.87(14) . . ?
O2 C5 C6 119.87(15) . . ?
C6 C5 C1 121.25(13) . . ?
C7 C6 C5 122.58(15) . . ?
C11 C6 C5 118.40(14) . . ?
C11 C6 C7 118.95(15) . . ?
C8 C7 C6 120.22(16) . . ?
C9 C8 C7 120.10(16) . . ?
C8 C9 C10 120.07(16) . . ?
C11 C10 C9 120.12(17) . . ?
C10 C11 C6 120.55(16) . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_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 2.148
_oxdiff_exptl_absorpt_empirical_full_min 0.471

####################################################################### 
# 
# 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_jcm008
_database_code_depnum_ccdc_archive 'CCDC 2046136'
loop_
_audit_author_name
_audit_author_address
'Kristof Van Hecke'
;Ghent University
Belgium
;
_audit_update_record             
;
2020-11-24 deposited with the CCDC.	2021-02-01 downloaded from the CCDC.
;
_audit_creation_date             2019-05-24
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H12 O6'
_chemical_formula_sum            'C7 H12 O6'
_chemical_formula_weight         192.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C7 H12 O6'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6334(2)
_cell_length_b                   8.7609(3)
_cell_length_c                   14.2366(3)
_cell_angle_alpha                81.705(2)
_cell_angle_beta                 88.677(2)
_cell_angle_gamma                73.562(3)
_cell_volume                     903.45(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14607
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      75.0890
_cell_measurement_theta_min      5.2870
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.090
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.643
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 1 -4 0.0148
0 -5 -2 0.1104
1 6 0 0.1705
0 0 -9 0.0649
0 0 9 0.0349
-4 -1 4 0.0724
-4 1 5 0.0846

_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.087
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.0010 0.9979 -3.9968 0.5177 -0.7468 -0.1732
0.0011 -4.9971 -1.9953 0.1091 -0.2475 0.8795
0.9988 5.9953 -0.0048 -0.0599 -0.0284 -1.0685
-0.0013 -0.0060 -9.0017 -0.4418 -0.8745 -0.0948
0.0013 0.0060 9.0017 0.4418 0.8745 0.0948
-4.0010 -0.9979 3.9968 -0.5177 0.7468 0.1732
-4.0014 1.0011 4.9950 -0.5515 0.8653 -0.1765

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32011
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.275
_diffrn_reflns_theta_min         3.138
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00-150.00  100
  2  ω   -116.00 -17.00   1.00    1.00    --  -41.80 -38.00  60.00   99
  3  ω   -116.00 -17.00   1.00    1.00    --  -41.80 -38.00 -30.00   99
  4  ω    -66.00  32.00   1.00    1.00    --  -41.80  38.00 150.00   98
  5  ω     23.00  98.00   1.00    1.00    --   41.80-125.00 -60.00   75
  6  ω    -30.00  70.00   1.00    1.00    --   41.80 -57.00   0.00  100
  7  ω     12.00  45.00   1.00    1.00    --   46.00  81.00  76.01   33
  8  ω     11.00  38.00   1.00    1.00    --   46.00  84.00 157.99   27
  9  ω     17.00  45.00   1.00    1.00    --   50.00  79.00-122.30   28
 10  ω     16.00  45.00   1.00    1.00    --   50.00  82.00 -42.95   29
 11  ω     17.00  45.00   1.00    1.00    --   50.00  79.00-101.05   28
 12  ω     25.00 134.00   1.00    1.00    --   58.00  77.00 148.34  109
 13  ω     30.00 138.00   1.00    1.00    --   62.00  76.00  31.62  108
 14  ω     30.00 137.00   1.00    1.00    --   62.00  73.00  -2.60  107
 15  ω     31.00 136.00   1.00    1.00    --   62.00  71.00 -44.30  105
 16  ω     31.00 136.00   1.00    1.00    --   62.00  71.00 179.34  105
 17  ω     36.00 139.00   1.00    1.00    --   66.00  68.00 -19.48  103
 18  ω     34.00 141.00   1.00    1.00    --   66.00  75.00  73.90  107
 19  ω     39.00 144.00   1.00    1.00    --   70.00  70.00  28.03  105
 20  ω     39.00 144.00   1.00    1.00    --   70.00  70.00 122.33  105
 21  ω     37.00 146.00   1.00    1.00    --   70.00  77.00-119.99  109
 22  ω     41.00 150.00   1.00    1.00    --   74.00  77.00-154.52  109
 23  ω     47.00 151.00   1.00    4.00    --   78.00  69.00 -95.74  104
 24  ω     47.00 151.00   1.00    4.00    --   78.00  69.00  42.82  104
 25  ω     60.00 163.00   1.00    4.00    --   90.00  64.00  36.40  103
 26  ω     59.00 163.00   1.00    4.00    --   90.00  69.00 -85.23  104
 27  ω     63.00 168.00   1.00    4.00    --   94.00  71.00 -57.62  105
 28  ω     62.00 169.00   1.00    4.00    --   94.00  75.00 174.78  107
 29  ω     80.00 178.00   1.00    4.00    --  109.13  61.00 -90.00   98
 30  ω     33.00 142.00   1.00    4.00    --  109.13 -77.00  60.00  109
 31  ω     36.00 117.00   1.00    4.00    --  109.13-125.00 -60.00   81
 32  ω     80.00 178.00   1.00    4.00    --  109.13  61.00 120.00   98
 33  ω     83.00 178.00   1.00    4.00    --  109.13  45.00 120.00   95
 34  ω     77.00 178.00   1.00    4.00    --  109.13  77.00  60.00  101
 35  ω     80.00 178.00   1.00    4.00    --  109.13  61.00 150.00   98
 36  ω     80.00 178.00   1.00    4.00    --  109.13  61.00  60.00   98
 37  ω     80.00 178.00   1.00    4.00    --  109.13  61.00  30.00   98
 38  ω     26.00 110.00   1.00    4.00    --  109.13 -94.00  30.00   84
 39  ω     36.00 135.00   1.00    4.00    --  109.13 -45.00 120.00   99
 40  ω     80.00 178.00   1.00    4.00    --  109.13  61.00-120.00   98
 41  ω     26.00 110.00   1.00    4.00    --  109.13 -94.00 150.00   84
 42  ω     79.00 178.00   1.00    4.00    --  109.13  68.00 -14.05   99
 43  ω     80.00 178.00   1.00    4.00    --  109.13  61.00 -30.00   98
 44  ω     36.00 117.00   1.00    4.00    --  109.13-125.00   0.00   81
 45  ω     77.00 178.00   1.00    4.00    --  109.13  77.00-180.00  101
 46  ω     78.00 178.00   1.00    4.00    --  109.13  70.00-142.96  100
 47  ω     77.00 178.00   1.00    4.00    --  109.13  77.00 120.00  101
 48  ω     17.00 116.00   1.00    1.00    --   41.80  38.00 -60.00   99
 49  ω     13.00  45.00   1.00    1.00    --   46.00  78.00-102.01   32
 50  ω     13.00  45.00   1.00    1.00    --   46.00  79.00 -64.92   32
 51  ω     12.00  45.00   1.00    1.00    --   46.00  82.00   9.61   33
 52  ω     22.00 129.00   1.00    1.00    --   54.00  75.00-154.43  107
 53  ω     25.00 134.00   1.00    1.00    --   58.00  77.00  86.82  109
 54  ω     26.00 111.00   1.00    1.00    --   58.00  76.00  35.18   85
 55  ω     30.00 137.00   1.00    1.00    --   62.00  75.00 110.96  107
 56  ω     34.00 141.00   1.00    1.00    --   66.00  73.00  49.09  107
 57  ω     42.00 142.00   1.00    1.00    --   70.00  54.00  39.28  100
 58  ω     37.00 146.00   1.00    1.00    --   70.00  77.00-103.14  109
 59  ω     39.00 143.00   1.00    1.00    --   70.00  69.00-166.49  104
 60  ω     42.00 150.00   1.00    1.00    --   74.00  76.00-145.42  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1887452000
_diffrn_orient_matrix_UB_12      -0.0413972000
_diffrn_orient_matrix_UB_13      0.0490855000
_diffrn_orient_matrix_UB_21      -0.0922787000
_diffrn_orient_matrix_UB_22      0.0107137000
_diffrn_orient_matrix_UB_23      0.0971594000
_diffrn_orient_matrix_UB_31      0.0123118000
_diffrn_orient_matrix_UB_32      -0.1802579000
_diffrn_orient_matrix_UB_33      0.0106484000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3246
_reflns_number_total             3680
_reflns_odcompleteness_completeness 100.00
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3680
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0419
_refine_ls_restrained_S_all      1.046
_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)+(0.0657P)²+0.3443P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1176
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C3(H3A,H3B), C10(H10A,H10B), C13(H13A,H13B)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C4(H4A,H4B,H4C)
2.c Idealised tetrahedral OH refined as rotating group:
 O7(H7), O8(H8), O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O5 O 0.46343(14) -0.00570(13) 0.68169(7) 0.0212(2) Uani 1 1 d . . . . .
O7 O 0.15937(13) 0.87647(13) 0.72083(7) 0.0196(2) Uani 1 1 d . . . . .
H7 H 0.244624 0.917375 0.704788 0.029 Uiso 1 1 calc GR . . . .
O11 O 0.06064(14) 0.55638(13) 0.82477(7) 0.0213(2) Uani 1 1 d . . . . .
O8 O 0.37266(13) 0.65441(13) 0.80172(7) 0.0190(2) Uani 1 1 d . . . . .
H8 H 0.371727 0.606388 0.754834 0.029 Uiso 1 1 calc GR . . . .
O4 O 0.25117(14) 0.37342(13) 0.53863(7) 0.0204(2) Uani 1 1 d . . . . .
O1 O 0.36524(14) 0.30807(14) 0.78562(7) 0.0205(2) Uani 1 1 d . . . . .
H1 H 0.284019 0.385772 0.802349 0.031 Uiso 1 1 calc GR . . . .
O9 O 0.22206(15) 1.00254(14) 0.87771(7) 0.0235(3) Uani 1 1 d . . . . .
O12 O -0.10298(13) 0.80695(13) 0.84487(7) 0.0200(2) Uani 1 1 d . . . . .
O3 O 0.30536(15) 0.54355(14) 0.63100(7) 0.0225(2) Uani 1 1 d . . . . .
O2 O 0.14782(13) 0.23197(13) 0.70629(7) 0.0203(2) Uani 1 1 d . . . . .
H2 H 0.152894 0.158612 0.752075 0.030 Uiso 1 1 calc GR . . . .
O10 O 0.24115(14) 0.76675(13) 0.96961(7) 0.0200(2) Uani 1 1 d . . . . .
O6 O 0.61385(13) 0.18156(13) 0.64786(7) 0.0196(2) Uani 1 1 d . . . . .
C2 C 0.28785(18) 0.41501(18) 0.62038(9) 0.0169(3) Uani 1 1 d . . . . .
C9 C 0.22525(18) 0.86326(18) 0.88793(10) 0.0171(3) Uani 1 1 d . . . . .
C12 C 0.04715(18) 0.69626(18) 0.82615(9) 0.0164(3) Uani 1 1 d . . . . .
C6 C 0.77543(19) 0.0612(2) 0.62053(11) 0.0224(3) Uani 1 1 d . . . . .
H6A H 0.792051 -0.041281 0.663675 0.027 Uiso 1 1 calc R . . . .
H6B H 0.885249 0.098285 0.626429 0.027 Uiso 1 1 calc R . . . .
C5 C 0.47061(18) 0.13058(18) 0.67588(9) 0.0166(3) Uani 1 1 d . . . . .
C3 C 0.2329(2) 0.49604(19) 0.45488(10) 0.0221(3) Uani 1 1 d . . . . .
H3A H 0.340992 0.537829 0.449715 0.027 Uiso 1 1 calc R . . . .
H3B H 0.122496 0.586860 0.459278 0.027 Uiso 1 1 calc R . . . .
C10 C 0.2487(2) 0.8385(2) 1.05575(10) 0.0216(3) Uani 1 1 d . . . . .
H10A H 0.150597 0.940871 1.054051 0.026 Uiso 1 1 calc R . . . .
H10B H 0.368017 0.860371 1.061603 0.026 Uiso 1 1 calc R . . . .
C1 C 0.31196(18) 0.27165(18) 0.70107(10) 0.0173(3) Uani 1 1 d . . . . .
C8 C 0.20714(18) 0.77186(18) 0.80501(10) 0.0168(3) Uani 1 1 d . . . . .
C13 C -0.26614(19) 0.7524(2) 0.86846(10) 0.0222(3) Uani 1 1 d . . . . .
H13A H -0.272210 0.670764 0.828213 0.027 Uiso 1 1 calc R . . . .
H13B H -0.377045 0.844469 0.855159 0.027 Uiso 1 1 calc R . . . .
C11 C 0.2233(2) 0.7181(2) 1.13757(10) 0.0275(4) Uani 1 1 d . . . . .
H11A H 0.107438 0.693854 1.129142 0.041 Uiso 1 1 calc GR . . . .
H11B H 0.221626 0.762710 1.196983 0.041 Uiso 1 1 calc GR . . . .
H11C H 0.324277 0.619245 1.139936 0.041 Uiso 1 1 calc GR . . . .
C7 C 0.7543(2) 0.0346(3) 0.51990(12) 0.0323(4) Uani 1 1 d . . . . .
H7A H 0.741378 0.135492 0.477125 0.048 Uiso 1 1 calc GR . . . .
H7B H 0.645423 -0.001877 0.514185 0.048 Uiso 1 1 calc GR . . . .
H7C H 0.862404 -0.047298 0.502818 0.048 Uiso 1 1 calc GR . . . .
C14 C -0.2609(2) 0.6812(2) 0.97137(11) 0.0275(4) Uani 1 1 d . . . . .
H14A H -0.152351 0.588755 0.984197 0.041 Uiso 1 1 calc GR . . . .
H14B H -0.370805 0.646186 0.985780 0.041 Uiso 1 1 calc GR . . . .
H14C H -0.255998 0.762395 1.011178 0.041 Uiso 1 1 calc GR . . . .
C4 C 0.2180(3) 0.4157(2) 0.37024(11) 0.0310(4) Uani 1 1 d . . . . .
H4A H 0.199143 0.495001 0.312633 0.046 Uiso 1 1 calc GR . . . .
H4B H 0.114331 0.370055 0.377924 0.046 Uiso 1 1 calc GR . . . .
H4C H 0.330694 0.329683 0.364956 0.046 Uiso 1 1 calc GR . . . .


_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
O5 C5 1.2015(19) . ?
O7 C8 1.3869(17) . ?
O11 C12 1.2034(19) . ?
O8 C8 1.3902(17) . ?
O4 C2 1.3270(17) . ?
O4 C3 1.4657(17) . ?
O1 C1 1.3867(17) . ?
O9 C9 1.2012(19) . ?
O12 C12 1.3253(18) . ?
O12 C13 1.4710(16) . ?
O3 C2 1.2017(19) . ?
O2 C1 1.3896(17) . ?
O10 C9 1.3216(17) . ?
O10 C10 1.4659(17) . ?
O6 C6 1.4643(17) . ?
O6 C5 1.3263(17) . ?
C2 C1 1.547(2) . ?
C9 C8 1.5482(19) . ?
C12 C8 1.5505(19) . ?
C6 C7 1.504(2) . ?
C5 C1 1.544(2) . ?
C3 C4 1.502(2) . ?
C10 C11 1.503(2) . ?
C13 C14 1.504(2) . ?

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
C2 O4 C3 116.18(12) . . ?
C12 O12 C13 116.78(12) . . ?
C9 O10 C10 116.69(12) . . ?
C5 O6 C6 116.85(12) . . ?
O4 C2 C1 110.30(12) . . ?
O3 C2 O4 125.60(13) . . ?
O3 C2 C1 124.07(13) . . ?
O9 C9 O10 126.07(13) . . ?
O9 C9 C8 123.78(13) . . ?
O10 C9 C8 110.13(12) . . ?
O11 C12 O12 125.89(13) . . ?
O11 C12 C8 123.66(13) . . ?
O12 C12 C8 110.46(12) . . ?
O6 C6 C7 110.27(12) . . ?
O5 C5 O6 125.52(13) . . ?
O5 C5 C1 124.08(12) . . ?
O6 C5 C1 110.40(12) . . ?
O4 C3 C4 106.65(13) . . ?
O10 C10 C11 106.29(12) . . ?
O1 C1 O2 113.72(11) . . ?
O1 C1 C2 111.31(12) . . ?
O1 C1 C5 105.36(11) . . ?
O2 C1 C2 106.61(11) . . ?
O2 C1 C5 111.26(12) . . ?
C5 C1 C2 108.53(11) . . ?
O7 C8 O8 113.75(11) . . ?
O7 C8 C9 111.14(12) . . ?
O7 C8 C12 105.79(11) . . ?
O8 C8 C9 106.32(11) . . ?
O8 C8 C12 111.41(12) . . ?
C9 C8 C12 108.38(10) . . ?
O12 C13 C14 110.67(12) . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_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 3.770
_oxdiff_exptl_absorpt_empirical_full_min 0.575

