# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_lc-0328
_audit_block_doi                 10.5517/ccdc.csd.cc1zqfgl
_database_code_depnum_ccdc_archive 'CCDC 1838810'
_audit_update_record             
;
2018-04-23 deposited with the CCDC.
2018-08-29 downloaded from the CCDC.
;
_audit_creation_date             2018-03-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H19 Cl O2'
_chemical_formula_sum            'C18 H19 Cl O2'
_chemical_formula_weight         302.78
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.9261(3)
_cell_length_b                   10.6284(3)
_cell_length_c                   12.9254(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.813(3)
_cell_angle_gamma                90
_cell_volume                     1500.84(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4076
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.7340
_cell_measurement_theta_min      5.3010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.260
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6356
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.182
_diffrn_reflns_theta_min         5.264
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  69.00   1.00    1.00    --   41.11 -57.00  60.00   93
  2  ω     67.00 132.00   1.00    1.00    --  106.95 -45.00   0.00   65
  3  ω     55.00  97.00   1.00    1.00    --   41.11-125.00-180.00   42
  4  ω     32.00  86.00   1.00    1.00    --  106.95 -95.00 -90.00   54
  5  ω    -75.00 -35.00   1.00    1.00    --  -41.11 -38.00-180.00   40
  6  ω    106.00 167.00   1.00    1.00    --  106.95 125.00 -90.00   61
  7  ω     99.00 167.00   1.00    1.00    --  106.95 125.00-180.00   68
  8  ω    137.00 164.00   1.00    1.00    --  106.95 125.00  90.00   27
  9  ω    -66.00 -17.00   1.00    1.00    --  -41.23 -38.00 -30.00   49
 10  ω   -114.00 -88.00   1.00    1.00    --  -41.23 -38.00 -30.00   26
 11  ω      3.00  46.00   1.00    1.00    --   41.23 -99.00-180.00   43
 12  ω     47.00  73.00   1.00    1.00    --   41.23 -99.00-180.00   26
 13  ω     95.00 121.00   1.00    1.00    --  106.95 125.00-150.00   26
 14  ω     35.00  61.00   1.00    1.00    --  106.95 -95.00-150.00   26
 15  ω     84.00 109.00   1.00    1.00    --  106.95 -95.00-120.00   25
 16  ω     54.00 132.00   1.00    1.00    --  106.95 -30.00  90.00   78
 17  ω     75.00 106.00   1.00    1.00    --  106.95 -95.00 -30.00   31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0981095000
_diffrn_orient_matrix_UB_12      -0.1033193000
_diffrn_orient_matrix_UB_13      -0.0118742000
_diffrn_orient_matrix_UB_21      0.0918134000
_diffrn_orient_matrix_UB_22      0.0994209000
_diffrn_orient_matrix_UB_23      -0.0376042000
_diffrn_orient_matrix_UB_31      0.0432019000
_diffrn_orient_matrix_UB_32      0.0219488000
_diffrn_orient_matrix_UB_33      0.1122781000
_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                2687
_reflns_number_total             2939
_reflns_odcompleteness_completeness 99.93
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2939
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0561
_refine_ls_restrained_S_all      1.042
_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)+(0.1090P)²+0.4885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1542
_refine_ls_wR_factor_ref         0.1588
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C14(H14), C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C13(H13A,H13B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C2(H2)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_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 0.78886(5) 0.18258(4) 0.50771(3) 0.0282(2) Uani 1 1 d . . . . .
O1 O 0.86973(13) 0.62081(14) 0.50814(11) 0.0284(3) Uani 1 1 d . . . . .
O2 O 0.95889(14) 0.57101(14) 0.65771(11) 0.0295(4) Uani 1 1 d . . . . .
C4 C 0.64908(17) 0.49993(18) 0.42306(14) 0.0208(4) Uani 1 1 d . . . . .
H4 H 0.634645 0.529903 0.489375 0.025 Uiso 1 1 calc R . . . .
C5 C 0.73150(16) 0.40090(18) 0.40930(14) 0.0207(4) Uani 1 1 d . . . . .
C3 C 0.58845(17) 0.55418(18) 0.33904(14) 0.0213(4) Uani 1 1 d . . . . .
C6 C 0.75077(17) 0.35380(18) 0.30995(15) 0.0223(4) Uani 1 1 d . . . . .
H6 H 0.802600 0.285416 0.300818 0.027 Uiso 1 1 calc R . . . .
C7 C 0.79649(16) 0.34682(19) 0.50004(14) 0.0213(4) Uani 1 1 d . . . . .
C8 C 0.85810(17) 0.40585(19) 0.57549(14) 0.0219(4) Uani 1 1 d . . . . .
C2 C 0.61195(17) 0.50822(18) 0.24025(14) 0.0222(4) Uani 1 1 d . . . . .
H2 H 0.572737 0.544870 0.183474 0.027 Uiso 1 1 calc R . . . .
C9 C 0.89041(17) 0.54257(19) 0.57293(14) 0.0238(4) Uani 1 1 d . . . . .
C1 C 0.69279(18) 0.40865(18) 0.22439(14) 0.0227(4) Uani 1 1 d . . . . .
C10 C 0.91555(17) 0.34836(19) 0.67078(15) 0.0229(4) Uani 1 1 d . . . . .
H10 H 0.971398 0.279367 0.654057 0.027 Uiso 1 1 calc R . . . .
C18 C 0.49739(19) 0.6589(2) 0.35392(17) 0.0268(4) Uani 1 1 d . . . . .
H18A H 0.416417 0.624219 0.357440 0.040 Uiso 1 1 calc GR . . . .
H18B H 0.501468 0.716303 0.296743 0.040 Uiso 1 1 calc GR . . . .
H18C H 0.516270 0.702801 0.417048 0.040 Uiso 1 1 calc GR . . . .
C14 C 0.82292(19) 0.31081(18) 0.75484(15) 0.0242(4) Uani 1 1 d . . . . .
H14 H 0.753114 0.261018 0.729705 0.029 Uiso 1 1 calc R . . . .
C11 C 0.98359(19) 0.4618(2) 0.72155(15) 0.0267(4) Uani 1 1 d . . . . .
H11 H 1.071635 0.445764 0.728701 0.032 Uiso 1 1 calc R . . . .
C17 C 0.7188(2) 0.3636(2) 0.11684(16) 0.0302(5) Uani 1 1 d . . . . .
H17A H 0.786769 0.409714 0.089697 0.045 Uiso 1 1 calc GR . . . .
H17B H 0.647985 0.376722 0.073405 0.045 Uiso 1 1 calc GR . . . .
H17C H 0.738410 0.275571 0.118656 0.045 Uiso 1 1 calc GR . . . .
C15 C 0.8961(2) 0.2508(2) 0.84457(16) 0.0298(5) Uani 1 1 d . . . . .
H15A H 0.951899 0.187073 0.819502 0.036 Uiso 1 1 calc R . . . .
H15B H 0.842044 0.213146 0.894749 0.036 Uiso 1 1 calc R . . . .
C12 C 0.9230(2) 0.4754(2) 0.82734(16) 0.0299(5) Uani 1 1 d . . . . .
H12 H 0.933532 0.557636 0.860500 0.036 Uiso 1 1 calc R . . . .
C13 C 0.78939(19) 0.4389(2) 0.80149(15) 0.0275(4) Uani 1 1 d . . . . .
H13A H 0.739231 0.431449 0.862510 0.033 Uiso 1 1 calc R . . . .
H13B H 0.751005 0.495055 0.751595 0.033 Uiso 1 1 calc R . . . .
C16 C 0.9666(2) 0.3632(2) 0.89184(16) 0.0315(5) Uani 1 1 d . . . . .
H16A H 0.946760 0.374264 0.964169 0.038 Uiso 1 1 calc R . . . .
H16B H 1.054326 0.351479 0.885999 0.038 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
Cl1 C7 1.751(2) . ?
O1 C9 1.199(2) . ?
O2 C9 1.352(2) . ?
O2 C11 1.448(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.398(3) . ?
C4 C3 1.389(3) . ?
C5 C6 1.397(3) . ?
C5 C7 1.479(3) . ?
C3 C2 1.394(3) . ?
C3 C18 1.507(3) . ?
C6 H6 0.9300 . ?
C6 C1 1.394(3) . ?
C7 C8 1.334(3) . ?
C8 C9 1.496(3) . ?
C8 C10 1.504(3) . ?
C2 H2 0.9300 . ?
C2 C1 1.395(3) . ?
C1 C17 1.501(3) . ?
C10 H10 0.9800 . ?
C10 C14 1.548(3) . ?
C10 C11 1.556(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C14 H14 0.9800 . ?
C14 C15 1.538(3) . ?
C14 C13 1.535(3) . ?
C11 H11 0.9800 . ?
C11 C12 1.534(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.543(3) . ?
C12 H12 0.9800 . ?
C12 C13 1.542(3) . ?
C12 C16 1.527(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

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
C9 O2 C11 112.28(15) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 120.92(17) . . ?
C4 C5 C7 119.64(17) . . ?
C6 C5 C4 119.50(17) . . ?
C6 C5 C7 120.86(17) . . ?
C4 C3 C2 118.58(17) . . ?
C4 C3 C18 121.00(17) . . ?
C2 C3 C18 120.40(17) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 C5 120.43(18) . . ?
C1 C6 H6 119.8 . . ?
C5 C7 Cl1 114.20(14) . . ?
C8 C7 Cl1 116.84(15) . . ?
C8 C7 C5 128.96(19) . . ?
C7 C8 C9 123.88(18) . . ?
C7 C8 C10 127.44(19) . . ?
C9 C8 C10 108.48(16) . . ?
C3 C2 H2 119.2 . . ?
C3 C2 C1 121.69(17) . . ?
C1 C2 H2 119.2 . . ?
O1 C9 O2 120.49(18) . . ?
O1 C9 C8 130.30(18) . . ?
O2 C9 C8 109.10(16) . . ?
C6 C1 C2 118.81(17) . . ?
C6 C1 C17 120.74(18) . . ?
C2 C1 C17 120.44(18) . . ?
C8 C10 H10 112.2 . . ?
C8 C10 C14 114.21(16) . . ?
C8 C10 C11 102.82(16) . . ?
C14 C10 H10 112.2 . . ?
C14 C10 C11 102.52(15) . . ?
C11 C10 H10 112.2 . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C14 H14 114.8 . . ?
C15 C14 C10 107.34(16) . . ?
C15 C14 H14 114.8 . . ?
C13 C14 C10 102.08(15) . . ?
C13 C14 H14 114.8 . . ?
C13 C14 C15 101.30(16) . . ?
O2 C11 C10 107.26(15) . . ?
O2 C11 H11 111.6 . . ?
O2 C11 C12 110.68(17) . . ?
C10 C11 H11 111.6 . . ?
C12 C11 C10 103.83(16) . . ?
C12 C11 H11 111.6 . . ?
C1 C17 H17A 109.5 . . ?
C1 C17 H17B 109.5 . . ?
C1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C15 H15A 111.1 . . ?
C14 C15 H15B 111.1 . . ?
C14 C15 C16 103.25(16) . . ?
H15A C15 H15B 109.1 . . ?
C16 C15 H15A 111.1 . . ?
C16 C15 H15B 111.1 . . ?
C11 C12 H12 115.1 . . ?
C11 C12 C13 101.67(15) . . ?
C13 C12 H12 115.1 . . ?
C16 C12 C11 106.11(18) . . ?
C16 C12 H12 115.1 . . ?
C16 C12 C13 102.07(17) . . ?
C14 C13 C12 94.45(16) . . ?
C14 C13 H13A 112.8 . . ?
C14 C13 H13B 112.8 . . ?
C12 C13 H13A 112.8 . . ?
C12 C13 H13B 112.8 . . ?
H13A C13 H13B 110.3 . . ?
C15 C16 H16A 111.0 . . ?
C15 C16 H16B 111.0 . . ?
C12 C16 C15 103.75(16) . . ?
C12 C16 H16A 111.0 . . ?
C12 C16 H16B 111.0 . . ?
H16A C16 H16B 109.0 . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.750
_oxdiff_exptl_absorpt_empirical_full_min 0.605
####################################################################### 
# 
# 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_exp_795
_database_code_depnum_ccdc_archive 'CCDC 1814490'
_audit_update_record             
;
2018-01-03 deposited with the CCDC.
2018-08-29 downloaded from the CCDC.
;
_audit_creation_date             2017-08-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 Cl O2'
_chemical_formula_sum            'C16 H15 Cl O2'
_chemical_formula_weight         274.73
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   6.07129(17)
_cell_length_b                   18.3833(5)
_cell_length_c                   12.0370(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.880(3)
_cell_angle_gamma                90
_cell_volume                     1314.67(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3941
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4130
_cell_measurement_theta_min      4.4670
_shelx_estimated_absorpt_T_max   0.703
_shelx_estimated_absorpt_T_min   0.619
_exptl_absorpt_coefficient_mu    2.524
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4776
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.261
_diffrn_reflns_theta_min         4.458
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     21.00  53.00   1.00    1.00    --   40.98  57.00 120.00   32
  2  ω    104.00 178.00   1.00    1.00    --  106.95  84.00 -44.00   74
  3  ω     97.00 172.00   1.00    1.00    --  106.95 125.00-180.00   75
  4  ω     82.00 159.00   1.00    1.00    --  106.95  45.00 -60.00   77
  5  ω     64.00 136.00   1.00    1.00    --  106.95 -61.00-150.00   72
  6  ω     50.00  89.00   1.00    1.00    --  106.95 -61.00-180.00   39
  7  ω     35.00 121.00   1.00    1.00    --  106.95-125.00-180.00   86
  8  ω     29.00  69.00   1.00    1.00    --   40.98-125.00  60.00   40
  9  ω   -108.00 -22.00   1.00    1.00    --  -40.98 -37.00 120.00   86
 10  ω    -75.00  -2.00   1.00    1.00    --  -40.98 125.00-150.00   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2494561000
_diffrn_orient_matrix_UB_12      0.0187393000
_diffrn_orient_matrix_UB_13      -0.0463609000
_diffrn_orient_matrix_UB_21      0.0293337000
_diffrn_orient_matrix_UB_22      0.0714883000
_diffrn_orient_matrix_UB_23      0.0682168000
_diffrn_orient_matrix_UB_31      0.0645960000
_diffrn_orient_matrix_UB_32      0.0395143000
_diffrn_orient_matrix_UB_33      -0.1014952000
_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                2494
_reflns_number_total             2576
_reflns_odcompleteness_completeness 99.88
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.703
_refine_diff_density_min         -0.732
_refine_diff_density_rms         0.134
_refine_ls_extinction_coef       0.0052(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2576
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0815
_refine_ls_restrained_S_all      1.034
_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)+(0.1662P)²+1.6926P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2215
_refine_ls_wR_factor_ref         0.2230
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14), C10(H10), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16A,H16B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.74754(10) 0.56554(4) 0.47917(6) 0.0215(3) Uani 1 1 d . . . . .
O1 O 0.1234(4) 0.72072(11) 0.48421(17) 0.0231(5) Uani 1 1 d . . . . .
O2 O 0.0875(4) 0.70999(11) 0.29711(17) 0.0236(5) Uani 1 1 d . . . . .
C1 C 0.5170(4) 0.63521(14) 0.6176(2) 0.0134(6) Uani 1 1 d . . . . .
C2 C 0.3281(4) 0.61543(14) 0.6608(2) 0.0140(6) Uani 1 1 d . . . . .
H2 H 0.204336 0.594285 0.613386 0.017 Uiso 1 1 calc R . . . .
C3 C 0.3259(4) 0.62742(15) 0.7742(2) 0.0159(6) Uani 1 1 d . . . . .
H3 H 0.200461 0.614332 0.802767 0.019 Uiso 1 1 calc R . . . .
C8 C 0.3795(5) 0.64328(14) 0.4033(2) 0.0156(6) Uani 1 1 d . . . . .
C6 C 0.7018(4) 0.66681(16) 0.6892(2) 0.0176(6) Uani 1 1 d . . . . .
H6 H 0.828063 0.679832 0.661152 0.021 Uiso 1 1 calc R . . . .
C7 C 0.5205(4) 0.62061(14) 0.4971(2) 0.0137(6) Uani 1 1 d . . . . .
C4 C 0.5105(5) 0.65893(16) 0.8453(2) 0.0191(6) Uani 1 1 d . . . . .
H4 H 0.508824 0.666639 0.921463 0.023 Uiso 1 1 calc R . . . .
C9 C 0.1892(5) 0.69418(15) 0.4049(2) 0.0180(6) Uani 1 1 d . . . . .
C11 C 0.3891(5) 0.62791(14) 0.2821(2) 0.0168(6) Uani 1 1 d . . . . .
H11 H 0.535992 0.640533 0.265683 0.020 Uiso 1 1 calc R . . . .
C5 C 0.6968(5) 0.67882(17) 0.8029(3) 0.0212(7) Uani 1 1 d . . . . .
H5 H 0.819444 0.700364 0.850532 0.025 Uiso 1 1 calc R . . . .
C14 C 0.0371(5) 0.62299(17) 0.1422(2) 0.0221(7) Uani 1 1 d . . . . .
H14 H -0.115529 0.641441 0.113867 0.026 Uiso 1 1 calc R . . . .
C13 C 0.0525(6) 0.55634(17) 0.2205(3) 0.0236(7) Uani 1 1 d . . . . .
H13A H -0.024485 0.514071 0.182800 0.028 Uiso 1 1 calc R . . . .
H13B H 0.001215 0.566364 0.290147 0.028 Uiso 1 1 calc R . . . .
C10 C 0.1971(5) 0.67632(15) 0.2139(2) 0.0203(6) Uani 1 1 d . . . . .
H10 H 0.254509 0.712516 0.167224 0.024 Uiso 1 1 calc R . . . .
C12 C 0.3125(5) 0.55049(16) 0.2388(2) 0.0202(6) Uani 1 1 d . . . . .
H12 H 0.379825 0.510569 0.288271 0.024 Uiso 1 1 calc R . . . .
C16 C 0.3447(5) 0.54571(19) 0.1161(3) 0.0247(7) Uani 1 1 d . . . . .
H16A H 0.326425 0.496104 0.088253 0.030 Uiso 1 1 calc R . . . .
H16B H 0.492432 0.563159 0.109899 0.030 Uiso 1 1 calc R . . . .
C15 C 0.1580(5) 0.59529(17) 0.0503(2) 0.0239(7) Uani 1 1 d . . . . .
H15A H 0.221416 0.635303 0.014757 0.029 Uiso 1 1 calc R . . . .
H15B H 0.055893 0.568153 -0.007550 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
Cl1 C7 1.759(3) . ?
O1 C9 1.211(4) . ?
O2 C9 1.349(3) . ?
O2 C10 1.450(3) . ?
C1 C2 1.401(4) . ?
C1 C6 1.393(4) . ?
C1 C7 1.480(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.389(4) . ?
C8 C7 1.336(4) . ?
C8 C9 1.490(4) . ?
C8 C11 1.498(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.393(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(4) . ?
C11 H11 0.9800 . ?
C11 C10 1.559(4) . ?
C11 C12 1.554(4) . ?
C5 H5 0.9300 . ?
C14 H14 0.9800 . ?
C14 C13 1.537(4) . ?
C14 C10 1.518(4) . ?
C14 C15 1.534(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.552(5) . ?
C10 H10 0.9800 . ?
C12 H12 0.9800 . ?
C12 C16 1.531(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C15 1.540(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?

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
C9 O2 C10 112.8(2) . . ?
C2 C1 C7 119.6(2) . . ?
C6 C1 C2 119.7(3) . . ?
C6 C1 C7 120.6(2) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C7 C8 C9 123.2(2) . . ?
C7 C8 C11 128.2(3) . . ?
C9 C8 C11 108.5(2) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 H6 120.1 . . ?
C1 C7 Cl1 113.22(19) . . ?
C8 C7 Cl1 117.2(2) . . ?
C8 C7 C1 129.5(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
O1 C9 O2 120.8(3) . . ?
O1 C9 C8 130.2(3) . . ?
O2 C9 C8 109.0(2) . . ?
C8 C11 H11 111.8 . . ?
C8 C11 C10 103.3(2) . . ?
C8 C11 C12 115.5(2) . . ?
C10 C11 H11 111.8 . . ?
C12 C11 H11 111.8 . . ?
C12 C11 C10 101.9(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H5 119.8 . . ?
C13 C14 H14 115.0 . . ?
C10 C14 H14 115.0 . . ?
C10 C14 C13 102.4(2) . . ?
C10 C14 C15 106.2(3) . . ?
C15 C14 H14 115.0 . . ?
C15 C14 C13 101.5(2) . . ?
C14 C13 H13A 112.9 . . ?
C14 C13 H13B 112.9 . . ?
C14 C13 C12 94.2(2) . . ?
H13A C13 H13B 110.3 . . ?
C12 C13 H13A 112.9 . . ?
C12 C13 H13B 112.9 . . ?
O2 C10 C11 106.2(2) . . ?
O2 C10 C14 109.7(3) . . ?
O2 C10 H10 112.0 . . ?
C11 C10 H10 112.0 . . ?
C14 C10 C11 104.6(2) . . ?
C14 C10 H10 112.0 . . ?
C11 C12 H12 115.0 . . ?
C13 C12 C11 102.1(2) . . ?
C13 C12 H12 115.0 . . ?
C16 C12 C11 106.7(2) . . ?
C16 C12 C13 101.3(2) . . ?
C16 C12 H12 115.0 . . ?
C12 C16 H16A 111.0 . . ?
C12 C16 H16B 111.0 . . ?
C12 C16 C15 103.6(2) . . ?
H16A C16 H16B 109.0 . . ?
C15 C16 H16A 111.0 . . ?
C15 C16 H16B 111.0 . . ?
C14 C15 C16 103.7(2) . . ?
C14 C15 H15A 111.0 . . ?
C14 C15 H15B 111.0 . . ?
C16 C15 H15A 111.0 . . ?
C16 C15 H15B 111.0 . . ?
H15A C15 H15B 109.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.1(4) . . . . ?
C1 C6 C5 C4 0.6(5) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
C2 C1 C7 Cl1 -122.0(2) . . . . ?
C2 C1 C7 C8 58.4(4) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 C6 -0.7(5) . . . . ?
C8 C11 C10 O2 -3.8(3) . . . . ?
C8 C11 C10 C14 -119.8(2) . . . . ?
C8 C11 C12 C13 76.4(3) . . . . ?
C8 C11 C12 C16 -177.8(2) . . . . ?
C6 C1 C2 C3 0.0(4) . . . . ?
C6 C1 C7 Cl1 56.5(3) . . . . ?
C6 C1 C7 C8 -123.1(3) . . . . ?
C7 C1 C2 C3 178.5(2) . . . . ?
C7 C1 C6 C5 -178.8(3) . . . . ?
C7 C8 C9 O1 -3.1(5) . . . . ?
C7 C8 C9 O2 176.3(3) . . . . ?
C7 C8 C11 C10 -173.7(3) . . . . ?
C7 C8 C11 C12 76.0(4) . . . . ?
C9 O2 C10 C11 4.1(3) . . . . ?
C9 O2 C10 C14 116.7(3) . . . . ?
C9 C8 C7 Cl1 -175.7(2) . . . . ?
C9 C8 C7 C1 3.9(5) . . . . ?
C9 C8 C11 C10 2.4(3) . . . . ?
C9 C8 C11 C12 -107.9(3) . . . . ?
C11 C8 C7 Cl1 -0.1(4) . . . . ?
C11 C8 C7 C1 179.4(3) . . . . ?
C11 C8 C9 O1 -179.5(3) . . . . ?
C11 C8 C9 O2 -0.1(3) . . . . ?
C11 C12 C16 C15 -71.3(3) . . . . ?
C14 C13 C12 C11 54.7(2) . . . . ?
C14 C13 C12 C16 -55.3(3) . . . . ?
C13 C14 C10 O2 -78.9(3) . . . . ?
C13 C14 C10 C11 34.7(3) . . . . ?
C13 C14 C15 C16 -35.0(3) . . . . ?
C13 C12 C16 C15 35.2(3) . . . . ?
C10 O2 C9 O1 176.8(3) . . . . ?
C10 O2 C9 C8 -2.6(3) . . . . ?
C10 C11 C12 C13 -34.8(3) . . . . ?
C10 C11 C12 C16 71.1(3) . . . . ?
C10 C14 C13 C12 -54.6(3) . . . . ?
C10 C14 C15 C16 71.7(3) . . . . ?
C12 C11 C10 O2 116.3(2) . . . . ?
C12 C11 C10 C14 0.3(3) . . . . ?
C12 C16 C15 C14 -0.3(3) . . . . ?
C15 C14 C13 C12 55.1(3) . . . . ?
C15 C14 C10 O2 175.0(2) . . . . ?
C15 C14 C10 C11 -71.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.053
_oxdiff_exptl_absorpt_empirical_full_min 0.313
