# Electronic Supplementary Material (ESI) for Organic & Biomolecular 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_mo_gscbs5_265_2_0ma
_database_code_depnum_ccdc_archive 'CCDC 2077452'
loop_
_audit_author_name
_audit_author_address
'Ramana babu'
;Indian Institute of Technology Hyderabad
India
;
_audit_update_record             
;
2021-04-14 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;
_audit_creation_date             2020-12-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        GSCBS5_265
_chemical_formula_moiety         '2(C17 H18 O)'
_chemical_formula_sum            'C34 H36 O2'
_chemical_formula_weight         476.63
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   4.787(7)
_cell_length_b                   13.87(2)
_cell_length_c                   21.66(2)
_cell_angle_alpha                72.77(5)
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1373(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    194
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      17.32
_cell_measurement_theta_min      2.94
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5774
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1039 before and 0.0612 after correction.
The Ratio of minimum to maximum transmission is 0.7745.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_recrystallization_method 'DCM +Hexane'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2286
_diffrn_reflns_av_unetI/netI     0.8537
_diffrn_reflns_Laue_measured_fraction_full 0.936
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7877
_diffrn_reflns_point_group_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.860
_diffrn_reflns_theta_min         1.969
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.936
_diffrn_measured_fraction_theta_max 0.889
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                745
_reflns_number_total             5234
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.050(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.838
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         5234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.5151
_refine_ls_R_factor_gt           0.1342
_refine_ls_restrained_S_all      0.838
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2736
_refine_ls_wR_factor_ref         0.5038
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C3(H3), C4(H4), C23(H23), C6(H6), C26(H26), C9(H9), C25(H25),
 C21(H21), C8(H8), C32(H32), C15(H15), C12(H12), C29(H29), C30(H30), C13(H13),
 C14(H14), C31(H31)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C34(H34A,H34B,H34C), C33(H33A,H33B,H33C), C16(H16A,H16B,
 H16C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1)
;
_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
O2 O 0.1777(17) 0.7526(8) 0.5321(4) 0.076(3) Uani 1 1 d . . . . .
H2 H 0.058298 0.761677 0.503794 0.115 Uiso 1 1 calc R U . . .
O1 O 0.6755(17) 0.7474(7) 0.4677(4) 0.072(3) Uani 1 1 d . . . . .
H1 H 0.564858 0.733038 0.497973 0.107 Uiso 1 1 calc R U . . .
C1 C 0.585(3) 0.7072(11) 0.4208(6) 0.057(4) Uani 1 1 d . . . . .
C18 C 0.086(3) 0.7931(12) 0.5804(7) 0.057(4) Uani 1 1 d . . . . .
C20 C 0.107(3) 0.7937(13) 0.6857(7) 0.075(5) Uani 1 1 d . . . . .
H20 H 0.177194 0.767202 0.727415 0.090 Uiso 1 1 calc R U . . .
C3 C 0.604(3) 0.7049(11) 0.3126(6) 0.067(4) Uani 1 1 d . . . . .
H3 H 0.671527 0.730344 0.270647 0.080 Uiso 1 1 calc R U . . .
C4 C 0.410(3) 0.6266(11) 0.3266(7) 0.068(4) Uani 1 1 d . . . . .
H4 H 0.349716 0.601201 0.293732 0.081 Uiso 1 1 calc R U . . .
C2 C 0.697(2) 0.7458(12) 0.3605(6) 0.065(4) Uani 1 1 d . . . . .
C23 C -0.096(3) 0.8728(13) 0.5672(7) 0.067(5) Uani 1 1 d . . . . .
H23 H -0.157768 0.899975 0.524904 0.081 Uiso 1 1 calc R U . . .
C5 C 0.309(2) 0.5868(11) 0.3868(7) 0.064(4) Uani 1 1 d . . . . .
C6 C 0.400(2) 0.6264(11) 0.4355(6) 0.062(4) Uani 1 1 d . . . . .
H6 H 0.336277 0.598887 0.477688 0.074 Uiso 1 1 calc R U . . .
C19 C 0.204(3) 0.7533(12) 0.6389(7) 0.064(4) Uani 1 1 d . . . . .
C24 C 0.412(2) 0.6696(11) 0.6563(6) 0.064(4) Uani 1 1 d . . . . .
H24A H 0.596371 0.698777 0.655141 0.077 Uiso 1 1 calc R U . . .
H24B H 0.406320 0.635143 0.623282 0.077 Uiso 1 1 calc R U . . .
C22 C -0.189(3) 0.9140(12) 0.6129(8) 0.064(4) Uani 1 1 d . . . . .
C7 C 0.907(2) 0.8308(11) 0.3438(6) 0.069(4) Uani 1 1 d . . . . .
H7A H 0.898489 0.865386 0.376729 0.083 Uiso 1 1 calc R U . . .
H7B H 1.092803 0.801975 0.345530 0.083 Uiso 1 1 calc R U . . .
C26 C 0.545(3) 0.5766(11) 0.7686(7) 0.071(5) Uani 1 1 d . . . . .
H26 H 0.700354 0.618666 0.762890 0.085 Uiso 1 1 calc R U . . .
C9 C 1.038(3) 0.9285(13) 0.2314(9) 0.083(5) Uani 1 1 d . . . . .
H9 H 1.200939 0.890489 0.238089 0.100 Uiso 1 1 calc R U . . .
C25 C 0.372(3) 0.5904(12) 0.7225(8) 0.081(5) Uani 1 1 d . . . . .
H25 H 0.212712 0.550347 0.729071 0.098 Uiso 1 1 calc R U . . .
C21 C -0.088(3) 0.8717(14) 0.6751(8) 0.084(5) Uani 1 1 d . . . . .
H21 H -0.149414 0.894808 0.708952 0.100 Uiso 1 1 calc R U . . .
C8 C 0.869(3) 0.9067(12) 0.2795(9) 0.083(5) Uani 1 1 d . . . . .
H8 H 0.702772 0.942845 0.273430 0.099 Uiso 1 1 calc R U . . .
C17 C 0.099(2) 0.5010(10) 0.4051(6) 0.076(5) Uani 1 1 d . . . . .
H17A H -0.084693 0.527895 0.406837 0.114 Uiso 1 1 calc R U . . .
H17B H 0.146294 0.455698 0.446661 0.114 Uiso 1 1 calc R U . . .
H17C H 0.102560 0.465231 0.373364 0.114 Uiso 1 1 calc R U . . .
C10 C 1.016(4) 1.0039(17) 0.1670(10) 0.089(6) Uani 1 1 d . . . . .
C34 C -0.399(3) 0.9997(12) 0.5975(7) 0.090(5) Uani 1 1 d . . . . .
H34A H -0.383555 1.037984 0.552760 0.135 Uiso 1 1 calc R U . . .
H34B H -0.362490 1.042776 0.624017 0.135 Uiso 1 1 calc R U . . .
H34C H -0.584606 0.972560 0.605950 0.135 Uiso 1 1 calc R U . . .
C27 C 0.514(3) 0.4989(13) 0.8298(7) 0.074(5) Uani 1 1 d . . . . .
C32 C 0.347(4) 0.4133(17) 0.8377(9) 0.107(6) Uani 1 1 d . . . . .
H32 H 0.260669 0.405882 0.800849 0.128 Uiso 1 1 calc R U . . .
C28 C 0.637(4) 0.5052(17) 0.8838(10) 0.108(7) Uani 1 1 d . . . . .
C11 C 1.153(4) 0.993(2) 0.1158(13) 0.120(7) Uani 1 1 d . . . . .
C15 C 0.838(5) 1.086(2) 0.1644(9) 0.119(8) Uani 1 1 d . . . . .
H15 H 0.753062 1.089742 0.202191 0.143 Uiso 1 1 calc R U . . .
C12 C 1.111(4) 1.073(2) 0.0554(11) 0.128(8) Uani 1 1 d . . . . .
H12 H 1.202091 1.072418 0.017598 0.153 Uiso 1 1 calc R U . . .
C29 C 0.616(5) 0.433(2) 0.9426(12) 0.152(10) Uani 1 1 d . . . . .
H29 H 0.716489 0.438324 0.978107 0.182 Uiso 1 1 calc R U . . .
C30 C 0.443(6) 0.350(2) 0.9478(11) 0.153(11) Uani 1 1 d . . . . .
H30 H 0.422486 0.300561 0.987343 0.184 Uiso 1 1 calc R U . . .
C13 C 0.932(6) 1.151(2) 0.0564(13) 0.150(9) Uani 1 1 d . . . . .
H13 H 0.908369 1.203162 0.018087 0.179 Uiso 1 1 calc R U . . .
C14 C 0.787(5) 1.158(2) 0.1087(14) 0.147(9) Uani 1 1 d . . . . .
H14 H 0.660685 1.209985 0.106265 0.176 Uiso 1 1 calc R U . . .
C31 C 0.298(4) 0.3408(19) 0.8935(13) 0.154(9) Uani 1 1 d . . . . .
H31 H 0.175780 0.287756 0.896010 0.185 Uiso 1 1 calc R U . . .
C33 C 0.830(3) 0.5919(16) 0.8846(8) 0.138(8) Uani 1 1 d . . . . .
H33A H 0.912693 0.619408 0.842590 0.206 Uiso 1 1 calc R U . . .
H33B H 0.975149 0.567473 0.915991 0.206 Uiso 1 1 calc R U . . .
H33C H 0.725589 0.643478 0.895574 0.206 Uiso 1 1 calc R U . . .
C16 C 1.336(4) 0.9094(16) 0.1162(8) 0.127(7) Uani 1 1 d . . . . .
H16A H 1.490892 0.908276 0.144394 0.190 Uiso 1 1 calc R U . . .
H16B H 1.402771 0.917564 0.073158 0.190 Uiso 1 1 calc R U . . .
H16C H 1.233903 0.847180 0.131145 0.190 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 H2 0.8200 . ?
O2 C18 1.398(14) . ?
O1 H1 0.8200 . ?
O1 C1 1.368(12) . ?
C1 C2 1.366(15) . ?
C1 C6 1.390(16) . ?
C18 C23 1.367(17) . ?
C18 C19 1.347(16) . ?
C20 H20 0.9300 . ?
C20 C19 1.378(17) . ?
C20 C21 1.398(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.389(16) . ?
C3 C2 1.395(16) . ?
C4 H4 0.9300 . ?
C4 C5 1.348(15) . ?
C2 C7 1.512(17) . ?
C23 H23 0.9300 . ?
C23 C22 1.357(18) . ?
C5 C6 1.395(16) . ?
C5 C17 1.517(17) . ?
C6 H6 0.9300 . ?
C19 C24 1.488(18) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.538(18) . ?
C22 C21 1.388(17) . ?
C22 C34 1.516(19) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.489(17) . ?
C26 H26 0.9300 . ?
C26 C25 1.268(14) . ?
C26 C27 1.446(19) . ?
C9 H9 0.9300 . ?
C9 C8 1.279(18) . ?
C9 C10 1.48(2) . ?
C25 H25 0.9300 . ?
C21 H21 0.9300 . ?
C8 H8 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C10 C11 1.34(2) . ?
C10 C15 1.41(3) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C27 C32 1.40(2) . ?
C27 C28 1.336(19) . ?
C32 H32 0.9300 . ?
C32 C31 1.34(2) . ?
C28 C29 1.37(3) . ?
C28 C33 1.52(2) . ?
C11 C12 1.46(3) . ?
C11 C16 1.45(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.34(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.39(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.39(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.40(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.35(3) . ?
C14 H14 0.9300 . ?
C31 H31 0.9300 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O2 H2 109.5 . . ?
C1 O1 H1 109.5 . . ?
O1 C1 C6 120.6(12) . . ?
C2 C1 O1 117.1(13) . . ?
C2 C1 C6 122.1(12) . . ?
C23 C18 O2 121.5(14) . . ?
C19 C18 O2 115.3(15) . . ?
C19 C18 C23 123.1(14) . . ?
C19 C20 H20 117.7 . . ?
C19 C20 C21 124.6(15) . . ?
C21 C20 H20 117.7 . . ?
C4 C3 H3 119.6 . . ?
C4 C3 C2 120.9(13) . . ?
C2 C3 H3 119.6 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.5(13) . . ?
C5 C4 H4 119.3 . . ?
C1 C2 C3 117.1(13) . . ?
C1 C2 C7 123.1(12) . . ?
C3 C2 C7 119.8(13) . . ?
C18 C23 H23 118.5 . . ?
C22 C23 C18 123.1(14) . . ?
C22 C23 H23 118.5 . . ?
C4 C5 C6 118.6(13) . . ?
C4 C5 C17 123.8(13) . . ?
C6 C5 C17 117.6(13) . . ?
C1 C6 C5 119.7(12) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C18 C19 C20 114.0(15) . . ?
C18 C19 C24 126.2(15) . . ?
C20 C19 C24 119.7(14) . . ?
C19 C24 H24A 108.2 . . ?
C19 C24 H24B 108.2 . . ?
C19 C24 C25 116.3(12) . . ?
H24A C24 H24B 107.4 . . ?
C25 C24 H24A 108.2 . . ?
C25 C24 H24B 108.2 . . ?
C23 C22 C21 116.4(16) . . ?
C23 C22 C34 122.1(15) . . ?
C21 C22 C34 121.5(17) . . ?
C2 C7 H7A 108.5 . . ?
C2 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C8 C7 C2 115.3(11) . . ?
C8 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
C25 C26 H26 118.3 . . ?
C25 C26 C27 123.5(15) . . ?
C27 C26 H26 118.3 . . ?
C8 C9 H9 114.6 . . ?
C8 C9 C10 130.8(18) . . ?
C10 C9 H9 114.6 . . ?
C24 C25 H25 118.2 . . ?
C26 C25 C24 123.7(14) . . ?
C26 C25 H25 118.2 . . ?
C20 C21 H21 120.7 . . ?
C22 C21 C20 118.5(16) . . ?
C22 C21 H21 120.7 . . ?
C7 C8 H8 116.0 . . ?
C9 C8 C7 128.0(17) . . ?
C9 C8 H8 116.0 . . ?
C5 C17 H17A 109.5 . . ?
C5 C17 H17B 109.5 . . ?
C5 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C11 C10 C9 122(2) . . ?
C11 C10 C15 124(2) . . ?
C15 C10 C9 115(2) . . ?
C22 C34 H34A 109.5 . . ?
C22 C34 H34B 109.5 . . ?
C22 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C32 C27 C26 123.2(15) . . ?
C28 C27 C26 122.1(18) . . ?
C28 C27 C32 114.7(18) . . ?
C27 C32 H32 116.9 . . ?
C31 C32 C27 126(2) . . ?
C31 C32 H32 116.9 . . ?
C27 C28 C29 124(2) . . ?
C27 C28 C33 122.3(19) . . ?
C29 C28 C33 113(2) . . ?
C10 C11 C12 116(2) . . ?
C10 C11 C16 125(3) . . ?
C16 C11 C12 119(3) . . ?
C10 C15 H15 119.2 . . ?
C14 C15 C10 122(2) . . ?
C14 C15 H15 119.2 . . ?
C11 C12 H12 121.2 . . ?
C13 C12 C11 118(2) . . ?
C13 C12 H12 121.2 . . ?
C28 C29 H29 120.7 . . ?
C28 C29 C30 119(2) . . ?
C30 C29 H29 120.7 . . ?
C29 C30 H30 119.9 . . ?
C29 C30 C31 120(2) . . ?
C31 C30 H30 119.9 . . ?
C12 C13 H13 117.3 . . ?
C14 C13 C12 125(3) . . ?
C14 C13 H13 117.3 . . ?
C15 C14 C13 116(3) . . ?
C15 C14 H14 121.9 . . ?
C13 C14 H14 121.9 . . ?
C32 C31 C30 116(2) . . ?
C32 C31 H31 121.9 . . ?
C30 C31 H31 121.9 . . ?
C28 C33 H33A 109.5 . . ?
C28 C33 H33B 109.5 . . ?
C28 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C18 C23 C22 180.0(12) . . . . ?
O2 C18 C19 C20 -179.3(12) . . . . ?
O2 C18 C19 C24 -2(2) . . . . ?
O1 C1 C2 C3 -179.8(12) . . . . ?
O1 C1 C2 C7 -1.3(19) . . . . ?
O1 C1 C6 C5 179.7(12) . . . . ?
C1 C2 C7 C8 -140.3(14) . . . . ?
C18 C23 C22 C21 1(2) . . . . ?
C18 C23 C22 C34 -177.6(12) . . . . ?
C18 C19 C24 C25 -138.8(14) . . . . ?
C20 C19 C24 C25 38.1(19) . . . . ?
C3 C4 C5 C6 1(2) . . . . ?
C3 C4 C5 C17 -179.7(13) . . . . ?
C3 C2 C7 C8 38(2) . . . . ?
C4 C3 C2 C1 -2(2) . . . . ?
C4 C3 C2 C7 180.0(13) . . . . ?
C4 C5 C6 C1 2(2) . . . . ?
C2 C1 C6 C5 -4(2) . . . . ?
C2 C3 C4 C5 -1(2) . . . . ?
C2 C7 C8 C9 -117.5(17) . . . . ?
C23 C18 C19 C20 6(2) . . . . ?
C23 C18 C19 C24 -177.4(14) . . . . ?
C23 C22 C21 C20 2(2) . . . . ?
C6 C1 C2 C3 4.0(19) . . . . ?
C6 C1 C2 C7 -177.6(13) . . . . ?
C19 C18 C23 C22 -5(2) . . . . ?
C19 C20 C21 C22 -2(2) . . . . ?
C19 C24 C25 C26 -114.9(16) . . . . ?
C26 C27 C32 C31 -176.7(19) . . . . ?
C26 C27 C28 C29 -178.9(19) . . . . ?
C26 C27 C28 C33 -3(3) . . . . ?
C9 C10 C11 C12 -179.9(15) . . . . ?
C9 C10 C11 C16 0(3) . . . . ?
C9 C10 C15 C14 -177.2(16) . . . . ?
C25 C26 C27 C32 21(3) . . . . ?
C25 C26 C27 C28 -157.2(17) . . . . ?
C21 C20 C19 C18 -2(2) . . . . ?
C21 C20 C19 C24 -179.5(13) . . . . ?
C8 C9 C10 C11 -155.2(19) . . . . ?
C8 C9 C10 C15 24(3) . . . . ?
C17 C5 C6 C1 -178.0(12) . . . . ?
C10 C9 C8 C7 -178.6(15) . . . . ?
C10 C11 C12 C13 -1(3) . . . . ?
C10 C15 C14 C13 -4(3) . . . . ?
C34 C22 C21 C20 -179.3(13) . . . . ?
C27 C26 C25 C24 -177.0(14) . . . . ?
C27 C32 C31 C30 -4(3) . . . . ?
C27 C28 C29 C30 -4(4) . . . . ?
C32 C27 C28 C29 3(3) . . . . ?
C32 C27 C28 C33 178.9(16) . . . . ?
C28 C27 C32 C31 1(3) . . . . ?
C28 C29 C30 C31 1(4) . . . . ?
C11 C10 C15 C14 2(3) . . . . ?
C11 C12 C13 C14 -1(4) . . . . ?
C15 C10 C11 C12 1(3) . . . . ?
C15 C10 C11 C16 -179.3(19) . . . . ?
C12 C13 C14 C15 4(4) . . . . ?
C29 C30 C31 C32 2(4) . . . . ?
C33 C28 C29 C30 179(2) . . . . ?
C16 C11 C12 C13 179(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'IN ACRYOLOOP WITH MINERAL OIL'
_olex2_submission_original_sample_id GSCBS5_265
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_c19h22o4_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2077542'
loop_
_audit_author_name
_audit_author_address
'Ramana babu'
;Indian Institute of Technology Hyderabad
India
;
_audit_update_record             
;
2021-04-14 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;
_audit_creation_date             2021-03-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H22 O4'
_chemical_formula_sum            'C19 H22 O4'
_chemical_formula_weight         314.36
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.4709(3)
_cell_length_b                   9.9830(3)
_cell_length_c                   11.1522(4)
_cell_angle_alpha                72.4800(10)
_cell_angle_beta                 75.8640(10)
_cell_angle_gamma                69.7340(10)
_cell_volume                     833.28(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4623
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.53
_cell_measurement_theta_min      2.59
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6965
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19020
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.139
_diffrn_reflns_theta_min         1.939
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2539
_reflns_number_total             3672
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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         0.194
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3672
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0454
_refine_ls_restrained_S_all      1.039
_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)+(0.0548P)²+0.1381P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1253
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00J(H00C,H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C00A(H00A), C00B(H00B), C00E(H00E), C00F(H00F), C00G(H00G),
 C00I(H00I)
2.c Idealised Me refined as rotating group:
 C00K(H00H,H00J,H00K), C00L(H00L,H00M,H00N), C00M(H00O,H00P,H00Q), C00N(H00R,
 H00S,H00T)
2.d Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_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
O001 O 0.00414(15) 0.68226(12) 0.13304(10) 0.0542(3) Uani 1 1 d . . . . .
O002 O 0.88136(14) 0.62258(13) 0.83869(12) 0.0576(3) Uani 1 1 d . . . . .
H002 H 0.906178 0.532608 0.856936 0.086 Uiso 1 1 calc GR . . . .
O003 O 0.25859(15) 0.78929(13) 0.11104(10) 0.0567(3) Uani 1 1 d . . . . .
O004 O -0.20935(16) 0.64015(14) 0.35178(12) 0.0641(4) Uani 1 1 d . . . . .
C005 C 0.1635(2) 0.76797(16) 0.22933(14) 0.0432(4) Uani 1 1 d . . . . .
C006 C 0.1928(2) 0.79423(16) 0.33562(14) 0.0432(4) Uani 1 1 d . . . . .
H006 H 0.283142 0.829876 0.329479 0.052 Uiso 1 1 calc R . . . .
C007 C 0.08735(19) 0.76740(16) 0.45201(14) 0.0431(4) Uani 1 1 d . . . . .
C008 C 0.0283(2) 0.71411(16) 0.23839(14) 0.0442(4) Uani 1 1 d . . . . .
C009 C 0.4452(2) 0.66303(16) 0.80189(14) 0.0435(4) Uani 1 1 d . . . . .
C00A C 0.2069(2) 0.86485(17) 0.58134(15) 0.0489(4) Uani 1 1 d . . . . .
H00A H 0.272943 0.904162 0.508533 0.059 Uiso 1 1 calc R . . . .
C00B C 0.6674(2) 0.83003(17) 0.75350(15) 0.0501(4) Uani 1 1 d . . . . .
H00B H 0.740943 0.886492 0.737049 0.060 Uiso 1 1 calc R . . . .
C00C C 0.3916(2) 0.81407(16) 0.74513(13) 0.0440(4) Uani 1 1 d . . . . .
C00D C 0.7198(2) 0.68152(16) 0.80896(14) 0.0436(4) Uani 1 1 d . . . . .
C00E C 0.6086(2) 0.59966(16) 0.83289(14) 0.0438(4) Uani 1 1 d . . . . .
H00E H 0.643896 0.499670 0.870674 0.053 Uiso 1 1 calc R . . . .
C00F C 0.1111(2) 0.79313(18) 0.56853(15) 0.0491(4) Uani 1 1 d . . . . .
H00F H 0.049533 0.752801 0.643626 0.059 Uiso 1 1 calc R . . . .
C00G C 0.5055(2) 0.89424(17) 0.72263(15) 0.0502(4) Uani 1 1 d . . . . .
H00G H 0.471358 0.994485 0.685529 0.060 Uiso 1 1 calc R . . . .
C00H C -0.0776(2) 0.68836(16) 0.35389(15) 0.0458(4) Uani 1 1 d . . . . .
C00I C -0.0465(2) 0.71289(17) 0.46021(14) 0.0470(4) Uani 1 1 d . . . . .
H00I H -0.115596 0.692768 0.538037 0.056 Uiso 1 1 calc R . . . .
C00J C 0.2171(2) 0.88792(18) 0.70633(16) 0.0536(4) Uani 1 1 d . . . . .
H00C H 0.134242 0.849803 0.772133 0.064 Uiso 1 1 calc R . . . .
H00D H 0.187192 0.992553 0.699880 0.064 Uiso 1 1 calc R . . . .
C00K C 0.3291(2) 0.56888(19) 0.83088(18) 0.0643(5) Uani 1 1 d . . . . .
H00H H 0.221925 0.614037 0.877128 0.096 Uiso 1 1 calc GR . . . .
H00J H 0.380317 0.473514 0.881324 0.096 Uiso 1 1 calc GR . . . .
H00K H 0.310985 0.558948 0.752709 0.096 Uiso 1 1 calc GR . . . .
C00L C 0.3988(2) 0.8428(2) 0.09440(18) 0.0651(5) Uani 1 1 d . . . . .
H00L H 0.458323 0.846892 0.008884 0.098 Uiso 1 1 calc GR . . . .
H00M H 0.474500 0.778362 0.153220 0.098 Uiso 1 1 calc GR . . . .
H00N H 0.358528 0.939575 0.109795 0.098 Uiso 1 1 calc GR . . . .
C00M C -0.1066(3) 0.8020(2) 0.05696(19) 0.0766(6) Uani 1 1 d . . . . .
H00O H -0.122869 0.770687 -0.011374 0.115 Uiso 1 1 calc GR . . . .
H00P H -0.056986 0.881401 0.022509 0.115 Uiso 1 1 calc GR . . . .
H00Q H -0.214547 0.834473 0.108466 0.115 Uiso 1 1 calc GR . . . .
C00N C -0.3274(2) 0.6202(2) 0.4657(2) 0.0709(5) Uani 1 1 d . . . . .
H00R H -0.415827 0.590499 0.450697 0.106 Uiso 1 1 calc GR . . . .
H00S H -0.376675 0.710950 0.492255 0.106 Uiso 1 1 calc GR . . . .
H00T H -0.269583 0.545687 0.531169 0.106 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
O001 C008 1.3823(17) . ?
O001 C00M 1.425(2) . ?
O002 C00D 1.3697(19) . ?
O003 C005 1.3656(18) . ?
O003 C00L 1.415(2) . ?
O004 C00H 1.3669(19) . ?
O004 C00N 1.421(2) . ?
C005 C006 1.383(2) . ?
C005 C008 1.396(2) . ?
C006 C007 1.395(2) . ?
C007 C00F 1.470(2) . ?
C007 C00I 1.391(2) . ?
C008 C00H 1.388(2) . ?
C009 C00C 1.404(2) . ?
C009 C00E 1.389(2) . ?
C009 C00K 1.502(2) . ?
C00A C00F 1.308(2) . ?
C00A C00J 1.506(2) . ?
C00B C00D 1.380(2) . ?
C00B C00G 1.378(2) . ?
C00C C00G 1.389(2) . ?
C00C C00J 1.510(2) . ?
C00D C00E 1.380(2) . ?
C00H C00I 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
C008 O001 C00M 113.89(12) . . ?
C005 O003 C00L 118.04(12) . . ?
C00H O004 C00N 117.69(13) . . ?
O003 C005 C006 125.31(14) . . ?
O003 C005 C008 114.67(13) . . ?
C006 C005 C008 120.01(14) . . ?
C005 C006 C007 120.18(14) . . ?
C006 C007 C00F 122.98(14) . . ?
C00I C007 C006 119.36(13) . . ?
C00I C007 C00F 117.66(13) . . ?
O001 C008 C005 119.66(13) . . ?
O001 C008 C00H 120.39(14) . . ?
C00H C008 C005 119.92(13) . . ?
C00C C009 C00K 121.38(14) . . ?
C00E C009 C00C 119.28(14) . . ?
C00E C009 C00K 119.34(14) . . ?
C00F C00A C00J 124.27(16) . . ?
C00G C00B C00D 119.65(15) . . ?
C009 C00C C00J 121.52(14) . . ?
C00G C00C C009 118.05(14) . . ?
C00G C00C C00J 120.42(14) . . ?
O002 C00D C00B 117.64(14) . . ?
O002 C00D C00E 123.05(14) . . ?
C00B C00D C00E 119.31(15) . . ?
C00D C00E C009 121.59(14) . . ?
C00A C00F C007 129.03(15) . . ?
C00B C00G C00C 122.13(14) . . ?
O004 C00H C008 115.37(13) . . ?
O004 C00H C00I 124.78(14) . . ?
C00I C00H C008 119.85(14) . . ?
C00H C00I C007 120.66(14) . . ?
C00A C00J C00C 113.03(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_9978
_database_code_depnum_ccdc_archive 'CCDC 2077652'
loop_
_audit_author_name
_audit_author_address
'Ramana babu'
;Indian Institute of Technology Hyderabad
India
;
_audit_update_record             
;
2021-04-14 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;
_audit_creation_date             2021-04-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H17 Br O'
_chemical_formula_sum            'C17 H17 Br O'
_chemical_formula_weight         317.21
_chemical_absolute_configuration ?
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.2775(7)
_cell_length_b                   5.2464(5)
_cell_length_c                   17.4065(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.906(7)
_cell_angle_gamma                90
_cell_volume                     754.94(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    741
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.5700
_cell_measurement_theta_min      2.6660
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.913
_exptl_absorpt_coefficient_mu    2.712
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.034
_exptl_crystal_size_mid          0.029
_exptl_crystal_size_min          0.025
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3212
_diffrn_reflns_point_group_measured_fraction_full 0.751
_diffrn_reflns_point_group_measured_fraction_max 0.619
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.959
_diffrn_reflns_theta_min         2.343
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00 -62.00   1.00   25.98    --  -18.08 -77.00 -60.00   26
  2  ω    -10.00  88.00   1.00   25.98    --   19.64  77.00 -30.00   98
  3  ω    -39.00  47.00   1.00   25.98    --   19.64 -77.00-180.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.285
_reflns_Friedel_fraction_full    0.435
_reflns_Friedel_fraction_max     0.307
_reflns_number_gt                1179
_reflns_number_total             2481
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 252 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2481
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1220
_refine_ls_R_factor_gt           0.0554
_refine_ls_restrained_S_all      0.977
_refine_ls_shift/su_max          1.977
_refine_ls_shift/su_mean         0.087
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1538
_refine_ls_wR_factor_ref         0.2172
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C10(H10), C14(H14), C13(H13), C16(H16), C11(H11), C17(H17)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
Br1 Br 0.30950(19) 1.0240(4) 0.62717(7) 0.1631(10) Uani 1 1 d . . . . .
O1 O 0.0438(7) 0.2650(13) 0.0326(4) 0.0824(18) Uani 1 1 d . . . . .
H1 H 0.015668 0.139816 0.007068 0.124 Uiso 1 1 calc GR . . . .
C6 C 0.2415(10) 0.3657(15) 0.1315(4) 0.062(2) Uani 1 1 d . . . . .
C1 C 0.1963(9) 0.2235(18) 0.0666(4) 0.066(2) Uani 1 1 d . . . . .
C2 C 0.3005(9) 0.050(2) 0.0377(5) 0.080(2) Uani 1 1 d . . . . .
H2 H 0.269328 -0.044393 -0.005800 0.097 Uiso 1 1 calc R . . . .
C9 C 0.1260(10) 0.554(2) 0.1635(5) 0.080(2) Uani 1 1 d . . . . .
H9A H 0.016740 0.493710 0.152154 0.096 Uiso 1 1 calc R . . . .
H9B H 0.137340 0.714627 0.136440 0.096 Uiso 1 1 calc R . . . .
C15 C 0.2684(12) 0.941(2) 0.5224(6) 0.084(3) Uani 1 1 d . . . . .
C12 C 0.2143(12) 0.830(2) 0.3695(5) 0.086(3) Uani 1 1 d . . . . .
C3 C 0.4529(11) 0.014(3) 0.0734(6) 0.094(3) Uani 1 1 d . . . . .
H3 H 0.522353 -0.108321 0.054606 0.113 Uiso 1 1 calc R . . . .
C10 C 0.1453(12) 0.606(2) 0.2482(6) 0.087(3) Uani 1 1 d . . . . .
H10 H 0.114080 0.471674 0.278798 0.105 Uiso 1 1 calc R . . . .
C5 C 0.3943(10) 0.330(2) 0.1656(6) 0.077(3) Uani 1 1 d . . . . .
H5 H 0.419(11) 0.427(18) 0.224(6) 0.092 Uiso 1 1 d R . . . .
C14 C 0.1761(14) 0.739(2) 0.5015(6) 0.096(3) Uani 1 1 d . . . . .
H14 H 0.130929 0.637776 0.538659 0.115 Uiso 1 1 calc R . . . .
C13 C 0.1488(13) 0.683(2) 0.4237(8) 0.104(4) Uani 1 1 d . . . . .
H13 H 0.085015 0.544227 0.408843 0.125 Uiso 1 1 calc R . . . .
C4 C 0.5011(12) 0.158(2) 0.1366(7) 0.106(4) Uani 1 1 d . . . . .
C16 C 0.3339(13) 1.088(2) 0.4690(7) 0.102(3) Uani 1 1 d . . . . .
H16 H 0.397268 1.227306 0.484290 0.122 Uiso 1 1 calc R . . . .
C11 C 0.1941(13) 0.792(2) 0.2844(8) 0.106(4) Uani 1 1 d . . . . .
H11 H 0.223306 0.930097 0.254703 0.127 Uiso 1 1 calc R . . . .
C17 C 0.3081(13) 1.035(3) 0.3920(7) 0.103(3) Uani 1 1 d . . . . .
H17 H 0.354156 1.136824 0.355377 0.124 Uiso 1 1 calc R . . . .
C7 C 0.6737(18) 0.150(4) 0.1744(11) 0.172(8) Uani 1 1 d . . . . .
H7A H 0.747555 0.216546 0.137858 0.206 Uiso 1 1 calc R . . . .
H7B H 0.677490 0.263970 0.218282 0.206 Uiso 1 1 calc R . . . .
C8 C 0.723(3) -0.053(5) 0.1957(17) 0.263(15) Uani 1 1 d . . . . .
H8A H 0.735990 -0.161259 0.152051 0.395 Uiso 1 1 calc GR . . . .
H8B H 0.647248 -0.128545 0.228891 0.395 Uiso 1 1 calc GR . . . .
H8C H 0.825434 -0.031646 0.223349 0.395 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
Br1 C15 1.890(9) . ?
O1 C1 1.384(9) . ?
C6 C1 1.389(11) . ?
C6 C9 1.503(12) . ?
C6 C5 1.383(11) . ?
C1 C2 1.368(13) . ?
C2 C3 1.390(11) . ?
C9 C10 1.500(13) . ?
C15 C14 1.346(16) . ?
C15 C16 1.342(15) . ?
C12 C13 1.352(16) . ?
C12 C11 1.497(16) . ?
C12 C17 1.369(17) . ?
C3 C4 1.379(15) . ?
C10 C11 1.216(14) . ?
C5 C4 1.376(14) . ?
C14 C13 1.393(16) . ?
C4 C7 1.543(15) . ?
C16 C17 1.376(15) . ?
C7 C8 1.19(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
C1 C6 C9 120.4(7) . . ?
C1 C6 C5 118.7(8) . . ?
C5 C6 C9 121.0(8) . . ?
C6 C1 O1 117.7(8) . . ?
C2 C1 O1 121.8(8) . . ?
C2 C1 C6 120.5(7) . . ?
C1 C2 C3 120.1(9) . . ?
C6 C9 C10 116.5(7) . . ?
C14 C15 Br1 120.9(10) . . ?
C16 C15 Br1 118.4(9) . . ?
C16 C15 C14 120.7(10) . . ?
C13 C12 C11 125.8(12) . . ?
C13 C12 C17 119.3(10) . . ?
C17 C12 C11 115.0(11) . . ?
C2 C3 C4 120.0(10) . . ?
C11 C10 C9 132.1(12) . . ?
C4 C5 C6 121.4(9) . . ?
C15 C14 C13 119.3(11) . . ?
C12 C13 C14 120.5(11) . . ?
C3 C4 C7 123.2(11) . . ?
C5 C4 C3 119.2(8) . . ?
C5 C4 C7 117.4(11) . . ?
C15 C16 C17 120.6(11) . . ?
C10 C11 C12 129.7(13) . . ?
C16 C17 C12 119.8(11) . . ?
C8 C7 C4 117(2) . . ?

_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
;
