# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_1059
_database_code_depnum_ccdc_archive 'CCDC 1854338'
_audit_update_record             
;
2018-07-07 deposited with the CCDC.
2019-02-08 downloaded from the CCDC.
;
_chemical_formula_moiety         'C19 H21 Br O3'
_chemical_formula_sum            'C19 H21 Br O3'
_chemical_formula_weight         377.28
_chemical_absolute_configuration rm
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z

_cell_length_a                   9.6654(18)
_cell_length_b                   5.3717(12)
_cell_length_c                   17.065(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.420(18)
_cell_angle_gamma                90
_cell_volume                     882.0(3)
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4403
_cell_measurement_theta_max      69.9870
_cell_measurement_theta_min      3.4620
_cell_formula_units_Z            2
_exptl_absorpt_coefficient_mu    2.342
_exptl_crystal_density_diffrn    1.4205
_exptl_crystal_F_000             388.0
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4672
_diffrn_reflns_theta_full        28.9436
_diffrn_reflns_theta_max         28.94
_diffrn_reflns_theta_min         3.60
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 0.6863
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.466
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              6
_reflns_limit_k_min              -7
_reflns_limit_l_max              23
_reflns_limit_l_min              -22
_reflns_number_gt                1931
_reflns_number_total             4672
_reflns_threshold_expression     I>=2u(I)
_refine_diff_density_max         0.7902
_refine_diff_density_min         -0.6905
_refine_diff_density_rms         0.1387
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.07(2)
_refine_ls_d_res_high            0.7343
_refine_ls_d_res_low             5.6628
_refine_ls_goodness_of_fit_ref   1.0588
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1239
_refine_ls_R_factor_gt           0.0709
_refine_ls_restrained_S_all      1.0588
_refine_ls_shift/su_max          0.0549
_refine_ls_shift/su_mean         0.0017
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0967P)²+0.4416P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2044
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  H12 of C12, H6 of C6, {H15a,H15b} of C15, {H14a,H14b} of C14, H13 of C13,
  H7 of C7, H10 of C10, H5 of C5, H4 of C4, {H17a,H17b} of C17, H20 of C20,
  {H16a,H16b} of C16, H9 of C9, H2 of C2
 At 1.5 times of:
  {H18a,H18b,H18c} of C18
2.a Ternary CH refined with riding coordinates:
 C20(H20), C13(H13), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17a,H17b), C16(H16a,H16b), C14(H14a,H14b), C15(H15a,H15b)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c)
;
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_refinement_flags_posn
Br21 Br -1.07504(9) -0.73832(10) -0.22791(5) 0.1061(6) Uani 1.000000 .
O18 O -0.8167(4) -0.4134(9) -0.1529(3) 0.0506(12) Uani 1.000000 .
O11 O -0.6696(5) -0.6782(8) -0.2534(3) 0.0541(13) Uani 1.000000 .
O23 O -0.8304(5) -0.6929(12) -0.0568(3) 0.079(2) Uani 1.000000 .
C19 C -0.8841(7) -0.5656(14) -0.1094(4) 0.0460(17) Uani 1.000000 .
C20 C -1.0378(7) -0.5517(14) -0.1316(5) 0.057(2) Uani 1.000000 .
C17 C -0.4583(8) -0.4380(14) -0.2165(5) 0.0525(19) Uani 1.000000 .
C13 C -0.6643(7) -0.4164(13) -0.1430(4) 0.0428(16) Uani 1.000000 .
C12 C -0.6144(7) -0.4465(13) -0.2236(4) 0.0423(16) Uani 1.000000 .
C16 C -0.4064(7) -0.1973(16) -0.1791(4) 0.061(2) Uani 1.000000 .
C1 C -0.7035(7) -0.7043(13) -0.3332(4) 0.0458(16) Uani 1.000000 .
C8 C -0.7879(8) -0.8021(14) -0.4916(4) 0.057(2) Uani 1.000000 .
C9 C -0.8337(9) -0.9458(15) -0.4311(5) 0.062(2) Uani 1.000000 .
C3 C -0.6951(8) -0.5985(14) -0.4697(5) 0.0537(19) Uani 1.000000 .
C2 C -0.6580(8) -0.5556(15) -0.3886(4) 0.0555(19) Uani 1.000000 .
C7 C -0.8257(11) -0.8396(17) -0.5720(5) 0.080(3) Uani 1.000000 .
C6 C -0.7790(11) -0.694(2) -0.6270(5) 0.087(3) Uani 1.000000 .
C14 C -0.6153(7) -0.1739(13) -0.1048(4) 0.0480(17) Uani 1.000000 .
C15 C -0.4564(8) -0.1639(15) -0.0978(4) 0.060(2) Uani 1.000000 .
C4 C -0.6482(10) -0.4500(17) -0.5301(5) 0.073(2) Uani 1.000000 .
C5 C -0.6879(13) -0.501(2) -0.6059(5) 0.093(3) Uani 1.000000 .
C10 C -0.7911(8) -0.9031(14) -0.3536(5) 0.058(2) Uani 1.000000 .
C18 C -1.1274(5) -0.6939(17) -0.0713(3) 0.053(2) Uani 1.000000 .
H10 H -0.8206(8) -1.0067(14) -0.3148(5) 0.069(2) Uiso 1.000000 R
H9 H -0.8955(9) -1.0754(15) -0.4440(5) 0.074(3) Uiso 1.000000 R
H2 H -0.6008(8) -0.4216(15) -0.3733(4) 0.067(2) Uiso 1.000000 R
H4 H -0.5892(10) -0.3163(17) -0.5173(5) 0.087(3) Uiso 1.000000 R
H5 H -0.6537(13) -0.404(2) -0.6450(5) 0.112(4) Uiso 1.000000 R
H6 H -0.8076(11) -0.723(2) -0.6798(5) 0.104(4) Uiso 1.000000 R
H7 H -0.8854(11) -0.9701(17) -0.5875(5) 0.096(4) Uiso 1.000000 R
H20 H -1.0684(7) -0.3785(14) -0.1388(5) 0.068(2) Uiso 1.000000 R
H17a H -0.4215(8) -0.5770(14) -0.1847(5) 0.063(2) Uiso 1.000000 R
H17b H -0.4256(8) -0.4533(14) -0.2683(5) 0.063(2) Uiso 1.000000 R
H13 H -0.6318(7) -0.5565(13) -0.1094(4) 0.0514(19) Uiso 1.000000 R
H12 H -0.6515(7) -0.3108(13) -0.2578(4) 0.0508(19) Uiso 1.000000 R
H16a H -0.3057(7) -0.1958(16) -0.1747(4) 0.073(2) Uiso 1.000000 R
H16b H -0.4392(7) -0.0591(16) -0.2125(4) 0.073(2) Uiso 1.000000 R
H14a H -0.6531(7) -0.0350(13) -0.1362(4) 0.058(2) Uiso 1.000000 R
H14b H -0.6480(7) -0.1612(13) -0.0529(4) 0.058(2) Uiso 1.000000 R
H15a H -0.4185(8) -0.2948(15) -0.0630(4) 0.071(3) Uiso 1.000000 R
H15b H -0.4246(8) -0.0051(15) -0.0759(4) 0.071(3) Uiso 1.000000 R
H18a H -1.2244(6) -0.662(8) -0.0849(19) 0.080(3) Uiso 1.000000 GR
H18b H -1.110(4) -0.8696(19) -0.074(2) 0.080(3) Uiso 1.000000 GR
H18c H -1.101(4) -0.636(7) -0.0188(5) 0.080(3) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br21 C20 1.929(8) .
O18 C19 1.318(8) .
O18 C13 1.466(8) .
O11 C12 1.428(8) .
O11 C1 1.376(8) .
O23 C19 1.206(9) .
C19 C20 1.500(10) .
C20 C18 1.600(9) .
C17 C12 1.503(9) .
C17 C16 1.507(11) .
C13 C12 1.509(9) .
C13 C14 1.512(10) .
C16 C15 1.521(10) .
C1 C2 1.344(10) .
C1 C10 1.387(11) .
C8 C9 1.394(11) .
C8 C3 1.441(11) .
C8 C7 1.401(11) .
C9 C10 1.367(12) .
C3 C2 1.415(11) .
C3 C4 1.412(12) .
C7 C6 1.333(13) .
C6 C5 1.388(15) .
C14 C15 1.531(10) .
C4 C5 1.342(13) .

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
C13 O18 C19 118.2(5) . .
C1 O11 C12 119.1(5) . .
O23 C19 O18 124.7(6) . .
C20 C19 O18 111.0(6) . .
C20 C19 O23 124.2(7) . .
C19 C20 Br21 106.8(5) . .
C18 C20 Br21 103.4(5) . .
C18 C20 C19 113.4(6) . .
C16 C17 C12 110.6(6) . .
C12 C13 O18 107.4(5) . .
C14 C13 O18 108.1(6) . .
C14 C13 C12 111.8(6) . .
C17 C12 O11 113.2(6) . .
C13 C12 O11 106.1(5) . .
C13 C12 C17 109.1(6) . .
C15 C16 C17 111.4(6) . .
C2 C1 O11 124.9(7) . .
C10 C1 O11 114.2(7) . .
C10 C1 C2 120.9(7) . .
C3 C8 C9 117.5(7) . .
C7 C8 C9 125.0(8) . .
C7 C8 C3 117.5(8) . .
C10 C9 C8 122.4(8) . .
C2 C3 C8 118.1(7) . .
C4 C3 C8 118.3(7) . .
C4 C3 C2 123.5(8) . .
C3 C2 C1 121.5(8) . .
C6 C7 C8 122.1(9) . .
C5 C6 C7 120.4(8) . .
C15 C14 C13 109.5(6) . .
C14 C15 C16 109.1(6) . .
C5 C4 C3 120.5(9) . .
C4 C5 C6 121.2(10) . .
C9 C10 C1 119.6(8) . .

####################################################################### 
# 
# 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_1012
_database_code_depnum_ccdc_archive 'CCDC 1854340'
_audit_update_record             
;
2018-07-07 deposited with the CCDC.
2019-02-08 downloaded from the CCDC.
;
_chemical_formula_moiety         'C26 H26 O5'
_chemical_formula_sum            'C26 H26 O5'
_chemical_formula_weight         418.49
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_cell_length_a                   8.2235(6)
_cell_length_b                   15.8364(13)
_cell_length_c                   17.2177(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2242.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2163
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.9400
_cell_measurement_theta_min      4.2630
_exptl_absorpt_coefficient_mu    0.085
_exptl_crystal_density_diffrn    1.2396
_exptl_crystal_F_000             888.4921
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13939
_diffrn_reflns_theta_full        28.9593
_diffrn_reflns_theta_max         28.96
_diffrn_reflns_theta_min         3.50
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 0.8669
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_reflns_Friedel_coverage         0.821
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              19
_reflns_limit_k_min              -19
_reflns_limit_l_max              23
_reflns_limit_l_min              -22
_reflns_number_gt                3857
_reflns_number_total             5147
_reflns_threshold_expression     I>=2u(I)
_refine_diff_density_max         0.2894
_refine_diff_density_min         -0.3311
_refine_diff_density_rms         0.0821
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.1(11)
_refine_ls_d_res_high            0.7339
_refine_ls_d_res_low             5.8279
_refine_ls_goodness_of_fit_ref   1.0707
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    46
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0551
_refine_ls_restrained_S_all      1.0707
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0637P)²+0.0510P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1265
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  H29 of C29, H8 of C8, H30 of C30, H7 of C7, H6 of C6, {H15a,H15b} of C15,
  {H16a,H16b} of C16, H9 of C9, H27 of C27, H31 of C31, H2 of C2, H3 of C3, H28
  of C28, H4 of C4, H12 of C12, H13 of C13, H20 of C20, {H17a,H17b} of C17,
  {H14a,H14b} of C14
 At 1.5 times of:
  {H24a,H24b,H24c} of C24
2.a Ternary CH refined with riding coordinates:
 C12(H12), C13(H13), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17a,H17b), C14(H14a,H14b), C15(H15a,H15b), C16(H16a,H16b)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C27(H27), C31(H31), C2(H2), C3(H3), C28(H28), C4(H4), C29(H29),
 C8(H8), C30(H30), C7(H7), C6(H6)
2.d Idealised Me refined as rotating group:
 C24(H24a,H24b,H24c)
;
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_refinement_flags_posn
O11 O 0.26314(16) 0.08356(8) 0.04388(8) 0.0404(3) Uani 1.000000 .
O18 O 0.40510(15) 0.13027(9) 0.18552(7) 0.0370(3) Uani 1.000000 .
O21 O 0.75296(17) 0.00250(10) 0.22763(9) 0.0506(4) Uani 1.000000 .
C12 C 0.2016(2) 0.15514(12) 0.08615(10) 0.0326(4) Uani 1.000000 .
H12 H 0.1167(2) 0.13621(12) 0.12211(10) 0.0391(5) Uiso 1.000000 R
C13 C 0.3410(2) 0.19243(12) 0.13204(10) 0.0323(4) Uani 1.000000 .
H13 H 0.4270(2) 0.21107(12) 0.09655(10) 0.0388(5) Uiso 1.000000 R
C20 C 0.5905(2) 0.03468(14) 0.23640(11) 0.0398(5) Uani 1.000000 .
H20 H 0.5839(2) 0.06630(14) 0.28523(11) 0.0478(6) Uiso 1.000000 R
C1 C 0.1567(2) 0.02173(13) 0.02183(11) 0.0392(5) Uani 1.000000 .
O25 O 0.62798(18) 0.10511(12) 0.11294(9) 0.0639(5) Uani 1.000000 .
C17 C 0.1317(3) 0.22120(13) 0.03220(11) 0.0416(5) Uani 1.000000 .
H17a H 0.2147(3) 0.23931(13) -0.00420(11) 0.0499(6) Uiso 1.000000 R
H17b H 0.0427(3) 0.19695(13) 0.00274(11) 0.0499(6) Uiso 1.000000 R
C19 C 0.5479(2) 0.09384(13) 0.16942(11) 0.0381(5) Uani 1.000000 .
C26 C 0.4793(2) -0.03998(13) 0.24126(11) 0.0387(5) Uani 1.000000 .
C10 C 0.2314(3) -0.04829(13) -0.01605(11) 0.0441(5) Uani 1.000000 .
C14 C 0.2810(3) 0.26642(13) 0.17940(12) 0.0453(5) Uani 1.000000 .
H14a H 0.2002(3) 0.24707(13) 0.21641(12) 0.0544(6) Uiso 1.000000 R
H14b H 0.3709(3) 0.29058(13) 0.20828(12) 0.0544(6) Uiso 1.000000 R
C15 C 0.2065(3) 0.33368(14) 0.12722(13) 0.0524(6) Uani 1.000000 .
H15a H 0.1636(3) 0.37914(14) 0.15895(13) 0.0628(7) Uiso 1.000000 R
H15b H 0.2900(3) 0.35700(14) 0.09368(13) 0.0628(7) Uiso 1.000000 R
C16 C 0.0708(3) 0.29680(14) 0.07789(13) 0.0506(6) Uani 1.000000 .
H16a H 0.0307(3) 0.33949(14) 0.04231(13) 0.0608(7) Uiso 1.000000 R
H16b H -0.0186(3) 0.27963(14) 0.11111(13) 0.0608(7) Uiso 1.000000 R
C9 C 0.4005(3) -0.05150(15) -0.02979(12) 0.0520(6) Uani 1.000000 .
H9 H 0.4664(3) -0.00678(15) -0.01445(12) 0.0624(7) Uiso 1.000000 R
C27 C 0.4155(3) -0.06229(16) 0.31250(13) 0.0519(6) Uani 1.000000 .
H27 H 0.4398(3) -0.02998(16) 0.35608(13) 0.0623(7) Uiso 1.000000 R
C31 C 0.4419(3) -0.08714(17) 0.17673(14) 0.0597(6) Uani 1.000000 .
H31 H 0.4832(3) -0.07207(17) 0.12839(14) 0.0716(8) Uiso 1.000000 R
C2 C -0.0081(3) 0.02364(16) 0.03373(14) 0.0535(6) Uani 1.000000 .
H2 H -0.0562(3) 0.06990(16) 0.05779(14) 0.0642(7) Uiso 1.000000 R
C5 C 0.1322(3) -0.11614(16) -0.04002(15) 0.0610(7) Uani 1.000000 .
C22 C 0.8759(3) 0.0562(2) 0.24410(18) 0.0676(8) Uani 1.000000 .
C3 C -0.1038(3) -0.04508(19) 0.00919(18) 0.0744(8) Uani 1.000000 .
H3 H -0.2155(3) -0.04398(19) 0.01758(18) 0.0893(10) Uiso 1.000000 R
C28 C 0.3176(3) -0.1310(2) 0.3196(2) 0.0737(8) Uani 1.000000 .
H28 H 0.2750(3) -0.1454(2) 0.3679(2) 0.0884(10) Uiso 1.000000 R
O23 O 0.8538(3) 0.12819(15) 0.25922(18) 0.1126(10) Uani 1.000000 .
C4 C -0.0364(4) -0.11241(19) -0.02623(18) 0.0812(9) Uani 1.000000 .
H4 H -0.1023(4) -0.15707(19) -0.04179(18) 0.0974(11) Uiso 1.000000 R
C29 C 0.2818(3) -0.17875(19) 0.2563(2) 0.0837(10) Uani 1.000000 .
H29 H 0.2160(3) -0.22617(19) 0.2617(2) 0.1004(12) Uiso 1.000000 R
C8 C 0.4675(4) -0.12007(19) -0.06554(16) 0.0737(8) Uani 1.000000 .
H8 H 0.5792(4) -0.12185(19) -0.07408(16) 0.0884(10) Uiso 1.000000 R
C30 C 0.3421(4) -0.1575(2) 0.1841(2) 0.0812(9) Uani 1.000000 .
H30 H 0.3163(4) -0.1900(2) 0.1408(2) 0.0975(11) Uiso 1.000000 R
C24 C 1.0349(3) 0.0114(2) 0.2430(2) 0.0900(12) Uani 1.000000 .
H24a H 1.0454(13) -0.0196(13) 0.1954(7) 0.1350(17) Uiso 1.000000 GR
H24b H 1.1215(3) 0.0518(3) 0.2469(14) 0.1350(17) Uiso 1.000000 GR
H24c H 1.0403(13) -0.0270(12) 0.2861(9) 0.1350(17) Uiso 1.000000 GR
C7 C 0.3709(5) -0.1874(2) -0.0894(2) 0.0900(10) Uani 1.000000 .
H7 H 0.4179(5) -0.2337(2) -0.1139(2) 0.1080(12) Uiso 1.000000 R
C6 C 0.2083(5) -0.18559(19) -0.07695(19) 0.0868(10) Uani 1.000000 .
H6 H 0.1452(5) -0.23106(19) -0.09304(19) 0.1042(12) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O11 C12 1.439(2) .
O11 C1 1.367(2) .
O18 C13 1.447(2) .
O18 C19 1.337(2) .
O21 C20 1.438(2) .
O21 C22 1.352(3) .
C12 C13 1.512(3) .
C12 C17 1.512(3) .
C13 C14 1.511(3) .
C20 C19 1.527(3) .
C20 C26 1.497(3) .
C1 C10 1.426(3) .
C1 C2 1.370(3) .
O25 C19 1.188(2) .
C17 C16 1.518(3) .
C26 C27 1.380(3) .
C26 C31 1.373(3) .
C10 C9 1.412(3) .
C10 C5 1.411(3) .
C14 C15 1.522(3) .
C15 C16 1.519(3) .
C9 C8 1.365(3) .
C27 C28 1.359(4) .
C31 C30 1.390(4) .
C2 C3 1.408(3) .
C5 C4 1.408(4) .
C5 C6 1.416(4) .
C22 O23 1.183(4) .
C22 C24 1.488(4) .
C3 C4 1.348(4) .
C28 C29 1.359(4) .
C29 C30 1.381(5) .
C8 C7 1.392(5) .
C7 C6 1.354(5) .

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
C1 O11 C12 118.65(15) . .
C19 O18 C13 118.77(14) . .
C22 O21 C20 116.74(19) . .
C13 C12 O11 107.77(15) . .
C17 C12 O11 111.59(15) . .
C17 C12 C13 109.80(16) . .
C12 C13 O18 110.05(15) . .
C14 C13 O18 107.65(14) . .
C14 C13 C12 109.71(16) . .
C19 C20 O21 110.57(16) . .
C26 C20 O21 107.08(17) . .
C26 C20 C19 112.75(16) . .
C10 C1 O11 114.10(17) . .
C2 C1 O11 125.1(2) . .
C2 C1 C10 120.8(2) . .
C16 C17 C12 110.66(15) . .
C20 C19 O18 108.04(15) . .
O25 C19 O18 126.28(18) . .
O25 C19 C20 125.68(18) . .
C27 C26 C20 118.95(19) . .
C31 C26 C20 121.39(19) . .
C31 C26 C27 119.6(2) . .
C9 C10 C1 122.0(2) . .
C5 C10 C1 118.5(2) . .
C5 C10 C9 119.6(2) . .
C15 C14 C13 110.84(16) . .
C16 C15 C14 110.89(19) . .
C15 C16 C17 110.51(19) . .
C8 C9 C10 120.2(2) . .
C28 C27 C26 120.7(3) . .
C30 C31 C26 119.6(3) . .
C3 C2 C1 119.4(2) . .
C4 C5 C10 119.2(2) . .
C6 C5 C10 117.8(3) . .
C6 C5 C4 122.9(3) . .
O23 C22 O21 122.5(2) . .
C24 C22 O21 110.7(3) . .
C24 C22 O23 126.7(3) . .
C4 C3 C2 121.2(3) . .
C29 C28 C27 120.1(3) . .
C3 C4 C5 121.0(3) . .
C30 C29 C28 120.6(3) . .
C7 C8 C9 120.8(3) . .
C29 C30 C31 119.3(3) . .
C6 C7 C8 120.1(3) . .
C7 C6 C5 121.6(3) . .

####################################################################### 
# 
# 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_1016
_database_code_depnum_ccdc_archive 'CCDC 1854341'
_audit_update_record             
;
2018-07-07 deposited with the CCDC.
2019-02-08 downloaded from the CCDC.
;
_chemical_formula_moiety         'C19 H21 Cl O3'
_chemical_formula_sum            'C19 H21 Cl O3'
_chemical_formula_weight         332.83
_chemical_absolute_configuration ad
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z

_cell_length_a                   9.3718(9)
_cell_length_b                   5.8521(4)
_cell_length_c                   16.3645(14)
_cell_angle_alpha                90
_cell_angle_beta                 106.047(9)
_cell_angle_gamma                90
_cell_volume                     862.54(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2163
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.9400
_cell_measurement_theta_min      4.2630
_exptl_absorpt_coefficient_mu    0.234
_exptl_crystal_density_diffrn    1.2814
_exptl_crystal_F_000             352.4639
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10572
_diffrn_reflns_theta_full        29.2402
_diffrn_reflns_theta_max         29.24
_diffrn_reflns_theta_min         3.71
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 0.8516
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_reflns_Friedel_coverage         0.785
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              7
_reflns_limit_k_min              -7
_reflns_limit_l_max              22
_reflns_limit_l_min              -21
_reflns_number_gt                3022
_reflns_number_total             3982
_reflns_threshold_expression     I>=2u(I)
_refine_diff_density_max         0.4185
_refine_diff_density_min         -0.4811
_refine_diff_density_rms         0.0647
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.00(14)
_refine_ls_d_res_high            0.7275
_refine_ls_d_res_low             5.4847
_refine_ls_goodness_of_fit_ref   1.0266
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3982
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0634
_refine_ls_restrained_S_all      1.0266
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0624P)²+0.2557P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1482
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  {H13a,H13b} of C13, {H15a,H15b} of C15, {H14a,H14b} of C14, H2 of C2, H12
  of C12, H3 of C3, H5 of C5, H10 of C10, H8 of C8, H6 of C6, H20 of C20, H17
  of C17, H7 of C7, {H16a,H16b} of C16
 At 1.5 times of:
  {H22a,H22b,H22c} of C22
2.a Ternary CH refined with riding coordinates:
 C12(H12), C20(H20), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16a,H16b), C13(H13a,H13b), C15(H15a,H15b), C14(H14a,H14b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C10(H10), C8(H8), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C22(H22a,H22b,H22c)
;
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_refinement_flags_posn
Cl21 Cl 1.24943(17) 0.0324(2) 0.24231(12) 0.1541(7) Uani 1.000000 .
O18 O 0.8944(2) 0.1147(3) 0.30233(11) 0.0500(5) Uani 1.000000 .
O11 O 0.7086(2) 0.4944(3) 0.27321(12) 0.0498(5) Uani 1.000000 .
O23 O 1.1236(3) 0.1118(4) 0.39182(16) 0.0818(8) Uani 1.000000 .
C19 C 1.0393(3) 0.0688(5) 0.32454(19) 0.0524(7) Uani 1.000000 .
C4 C 0.3986(3) 0.7762(4) 0.06289(16) 0.0375(6) Uani 1.000000 .
C1 C 0.5985(3) 0.5735(4) 0.20540(15) 0.0373(5) Uani 1.000000 .
C2 C 0.6327(3) 0.7830(4) 0.17226(16) 0.0423(6) Uani 1.000000 .
H2 H 0.7226(3) 0.8548(4) 0.19753(16) 0.0508(7) Uiso 1.000000 R
C9 C 0.3648(3) 0.5649(4) 0.09653(15) 0.0377(6) Uani 1.000000 .
C12 C 0.6803(3) 0.3015(5) 0.32109(17) 0.0443(6) Uani 1.000000 .
H12 H 0.6222(3) 0.1874(5) 0.28191(17) 0.0532(8) Uiso 1.000000 R
C3 C 0.5358(3) 0.8801(5) 0.10405(17) 0.0435(6) Uani 1.000000 .
H3 H 0.5602(3) 1.0190(5) 0.08372(17) 0.0522(7) Uiso 1.000000 R
C5 C 0.2965(3) 0.8711(5) -0.00949(18) 0.0485(7) Uani 1.000000 .
H5 H 0.3181(3) 1.0094(5) -0.03137(18) 0.0581(8) Uiso 1.000000 R
C10 C 0.4668(3) 0.4672(5) 0.16772(16) 0.0403(6) Uani 1.000000 .
H10 H 0.4443(3) 0.3290(5) 0.18934(16) 0.0484(7) Uiso 1.000000 R
C8 C 0.2274(3) 0.4594(5) 0.05525(18) 0.0507(7) Uani 1.000000 .
H8 H 0.2020(3) 0.3218(5) 0.07597(18) 0.0608(8) Uiso 1.000000 R
C6 C 0.1672(3) 0.7623(6) -0.0473(2) 0.0577(8) Uani 1.000000 .
H6 H 0.1019(3) 0.8253(6) -0.0954(2) 0.0693(10) Uiso 1.000000 R
C20 C 1.0780(3) -0.0596(6) 0.2529(2) 0.0597(9) Uani 1.000000 .
H20 H 1.0022(3) -0.0236(6) 0.1999(2) 0.0717(10) Uiso 1.000000 R
C17 C 0.8285(3) 0.2012(5) 0.36711(17) 0.0481(7) Uani 1.000000 .
H17 H 0.8922(3) 0.3203(5) 0.40051(17) 0.0577(8) Uiso 1.000000 R
C7 C 0.1317(3) 0.5575(6) -0.01464(19) 0.0574(8) Uani 1.000000 .
H7 H 0.0419(3) 0.4862(6) -0.04058(19) 0.0689(9) Uiso 1.000000 R
C16 C 0.8121(4) 0.0059(5) 0.42512(19) 0.0608(8) Uani 1.000000 .
H16a H 0.7593(4) -0.1196(5) 0.39114(19) 0.0730(10) Uiso 1.000000 R
H16b H 0.9096(4) -0.0487(5) 0.45649(19) 0.0730(10) Uiso 1.000000 R
C13 C 0.5953(4) 0.3747(5) 0.3830(2) 0.0612(9) Uani 1.000000 .
H13a H 0.6470(4) 0.5004(5) 0.4174(2) 0.0735(10) Uiso 1.000000 R
H13b H 0.4976(4) 0.4285(5) 0.3516(2) 0.0735(10) Uiso 1.000000 R
C15 C 0.7277(4) 0.0845(6) 0.4870(2) 0.0712(10) Uani 1.000000 .
H15a H 0.7147(4) -0.0434(6) 0.5220(2) 0.0854(12) Uiso 1.000000 R
H15b H 0.7848(4) 0.2010(6) 0.5242(2) 0.0854(12) Uiso 1.000000 R
C14 C 0.5789(5) 0.1793(6) 0.4407(2) 0.0752(11) Uani 1.000000 .
H14a H 0.5287(5) 0.2334(6) 0.4815(2) 0.0903(13) Uiso 1.000000 R
H14b H 0.5187(5) 0.0595(6) 0.4071(2) 0.0903(13) Uiso 1.000000 R
C22 C 1.0795(5) -0.3122(7) 0.2649(3) 0.0836(12) Uani 1.000000 .
H22a H 1.089(3) -0.3863(7) 0.2144(7) 0.1255(18) Uiso 1.000000 GR
H22b H 1.1618(19) -0.3538(8) 0.3121(12) 0.1255(18) Uiso 1.000000 GR
H22c H 0.9885(14) -0.3592(9) 0.2761(18) 0.1255(18) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl21 C20 1.747(3) .
O18 C19 1.332(3) .
O18 C17 1.457(4) .
O11 C1 1.370(3) .
O11 C12 1.440(3) .
O23 C19 1.191(3) .
C19 C20 1.519(5) .
C4 C9 1.424(3) .
C4 C3 1.414(4) .
C4 C5 1.415(4) .
C1 C2 1.413(4) .
C1 C10 1.368(3) .
C2 C3 1.354(4) .
C9 C10 1.408(3) .
C9 C8 1.420(4) .
C12 C17 1.504(4) .
C12 C13 1.514(4) .
C5 C6 1.357(4) .
C8 C7 1.369(4) .
C6 C7 1.390(5) .
C20 C22 1.491(5) .
C17 C16 1.521(4) .
C16 C15 1.519(5) .
C13 C14 1.518(4) .
C15 C14 1.498(5) .

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
C17 O18 C19 118.5(2) . .
C12 O11 C1 119.64(19) . .
O23 C19 O18 125.1(3) . .
C20 C19 O18 109.4(2) . .
C20 C19 O23 125.4(3) . .
C3 C4 C9 117.4(2) . .
C5 C4 C9 119.5(2) . .
C5 C4 C3 123.1(2) . .
C2 C1 O11 113.8(2) . .
C10 C1 O11 126.6(2) . .
C10 C1 C2 119.6(2) . .
C3 C2 C1 120.6(2) . .
C10 C9 C4 120.0(2) . .
C8 C9 C4 117.6(2) . .
C8 C9 C10 122.4(2) . .
C17 C12 O11 107.1(2) . .
C13 C12 O11 110.7(2) . .
C13 C12 C17 111.1(2) . .
C2 C3 C4 121.8(2) . .
C6 C5 C4 120.6(3) . .
C9 C10 C1 120.7(2) . .
C7 C8 C9 120.9(3) . .
C7 C6 C5 120.5(3) . .
C19 C20 Cl21 110.3(2) . .
C22 C20 Cl21 110.1(3) . .
C22 C20 C19 112.6(3) . .
C12 C17 O18 106.8(2) . .
C16 C17 O18 109.2(2) . .
C16 C17 C12 111.5(3) . .
C6 C7 C8 120.8(3) . .
C15 C16 C17 110.5(3) . .
C14 C13 C12 111.5(3) . .
C14 C15 C16 111.0(3) . .
C15 C14 C13 110.7(3) . .

####################################################################### 
# 
# 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_1046
_database_code_depnum_ccdc_archive 'CCDC 1854344'
_audit_update_record             
;
2018-07-07 deposited with the CCDC.
2019-02-08 downloaded from the CCDC.
;
_chemical_formula_moiety         'C26 H26 O5'
_chemical_formula_sum            'C26 H26 O5'
_chemical_formula_weight         418.49
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_cell_length_a                   9.3173(7)
_cell_length_b                   10.8597(9)
_cell_length_c                   22.3122(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2257.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2364
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.9400
_cell_measurement_theta_min      4.2630
_exptl_absorpt_coefficient_mu    0.085
_exptl_crystal_density_diffrn    1.2311
_exptl_crystal_F_000             888.4921
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            6917
_diffrn_reflns_theta_full        28.8037
_diffrn_reflns_theta_max         28.80
_diffrn_reflns_theta_min         3.32
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 0.7909
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_reflns_Friedel_coverage         0.671
_reflns_limit_h_max              11
_reflns_limit_h_min              -12
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              30
_reflns_limit_l_min              -29
_reflns_number_gt                3619
_reflns_number_total             5890
_reflns_threshold_expression     I>=2u(I)
_refine_diff_density_max         0.2692
_refine_diff_density_min         -0.2297
_refine_diff_density_rms         0.0527
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.8(13)
_refine_ls_d_res_high            0.7376
_refine_ls_d_res_low             6.1363
_refine_ls_goodness_of_fit_ref   1.0772
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    46
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4667
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0484
_refine_ls_restrained_S_all      1.0772
_refine_ls_shift/su_max          0.0025
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0318P)²+0.1906P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0972
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  {H14a,H14b} of C14, H7 of C7, {H17a,H17b} of C17, {H16a,H16b} of C16, H6 of
  C6, H5 of C5, H27 of C27, {H15a,H15b} of C15, H28 of C28, H29 of C29, H31 of
  C31, H30 of C30, H20 of C20, H12 of C12, H10 of C10, H13 of C13, H2 of C2, H8
  of C8, H3 of C3
 At 1.5 times of:
  {H24a,H24b,H24c} of C24
2.a Ternary CH refined with riding coordinates:
 C20(H20), C12(H12), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b), C17(H17a,H17b), C16(H16a,H16b), C15(H15a,H15b)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C2(H2), C8(H8), C3(H3), C7(H7), C6(H6), C5(H5), C27(H27), C28(H28),
 C29(H29), C31(H31), C30(H30)
2.d Idealised Me refined as rotating group:
 C24(H24a,H24b,H24c)
;
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_refinement_flags_posn
O11 O 0.32080(14) 0.87772(14) 0.11511(6) 0.0466(4) Uani 1.000000 .
O18 O 0.38919(14) 0.63819(13) 0.14675(6) 0.0423(4) Uani 1.000000 .
O21 O 0.30626(16) 0.36689(14) 0.06452(7) 0.0468(4) Uani 1.000000 .
C1 C 0.2031(2) 0.9513(2) 0.12528(10) 0.0403(5) Uani 1.000000 .
C20 C 0.2776(2) 0.46547(19) 0.10567(10) 0.0397(5) Uani 1.000000 .
H20 H 0.2741(2) 0.43211(19) 0.14646(10) 0.0476(6) Uiso 1.000000 R
C9 C 0.0409(2) 1.07539(18) 0.18367(9) 0.0367(5) Uani 1.000000 .
C4 C -0.0459(2) 1.09452(19) 0.13291(10) 0.0419(5) Uani 1.000000 .
C12 C 0.4167(2) 0.85474(18) 0.16406(9) 0.0358(5) Uani 1.000000 .
H12 H 0.3611(2) 0.84457(18) 0.20100(9) 0.0430(6) Uiso 1.000000 R
C10 C 0.1668(2) 1.00330(19) 0.17867(9) 0.0392(5) Uani 1.000000 .
H10 H 0.2250(2) 0.99140(19) 0.21203(9) 0.0470(6) Uiso 1.000000 R
O25 O 0.48814(19) 0.56130(17) 0.06399(8) 0.0718(6) Uani 1.000000 .
C13 C 0.4955(2) 0.73625(17) 0.15038(9) 0.0361(5) Uani 1.000000 .
H13 H 0.5466(2) 0.74362(17) 0.11216(9) 0.0433(5) Uiso 1.000000 R
C19 C 0.3986(2) 0.55902(19) 0.10179(9) 0.0365(5) Uani 1.000000 .
C2 C 0.1158(2) 0.9698(2) 0.07467(10) 0.0512(6) Uani 1.000000 .
H2 H 0.1407(2) 0.9337(2) 0.03833(10) 0.0614(7) Uiso 1.000000 R
C8 C -0.0002(2) 1.1293(2) 0.23834(10) 0.0457(5) Uani 1.000000 .
H8 H 0.0551(2) 1.1156(2) 0.27242(10) 0.0549(6) Uiso 1.000000 R
C3 C -0.0047(3) 1.0400(2) 0.07840(10) 0.0530(6) Uani 1.000000 .
H3 H -0.0606(3) 1.0521(2) 0.04439(10) 0.0636(7) Uiso 1.000000 R
C14 C 0.5999(2) 0.7051(2) 0.19990(11) 0.0489(6) Uani 1.000000 .
H14a H 0.5470(2) 0.6869(2) 0.23626(11) 0.0587(7) Uiso 1.000000 R
H14b H 0.6536(2) 0.6320(2) 0.18887(11) 0.0587(7) Uiso 1.000000 R
C26 C 0.1326(2) 0.5185(2) 0.09016(9) 0.0401(5) Uani 1.000000 .
C7 C -0.1201(2) 1.2015(2) 0.24217(12) 0.0537(6) Uani 1.000000 .
H7 H -0.1448(2) 1.2375(2) 0.27855(12) 0.0644(8) Uiso 1.000000 R
C17 C 0.5241(2) 0.95823(19) 0.17230(10) 0.0454(5) Uani 1.000000 .
H17a H 0.5793(2) 0.96889(19) 0.13581(10) 0.0545(6) Uiso 1.000000 R
H17b H 0.4737(2) 1.03457(19) 0.18043(10) 0.0545(6) Uiso 1.000000 R
C16 C 0.6241(2) 0.9288(2) 0.22384(11) 0.0520(6) Uani 1.000000 .
H16a H 0.6924(2) 0.9953(2) 0.22892(11) 0.0624(7) Uiso 1.000000 R
H16b H 0.5691(2) 0.9212(2) 0.26058(11) 0.0624(7) Uiso 1.000000 R
C6 C -0.2051(2) 1.2212(2) 0.19207(12) 0.0549(7) Uani 1.000000 .
H6 H -0.2865(2) 1.2703(2) 0.19514(12) 0.0658(8) Uiso 1.000000 R
C5 C -0.1704(2) 1.1696(2) 0.13855(11) 0.0499(6) Uani 1.000000 .
H5 H -0.2285(2) 1.1834(2) 0.10532(11) 0.0598(7) Uiso 1.000000 R
O23 O 0.4710(2) 0.2952(2) 0.12765(10) 0.1039(8) Uani 1.000000 .
C22 C 0.4096(3) 0.2863(2) 0.08120(13) 0.0624(7) Uani 1.000000 .
C27 C 0.0122(2) 0.4643(2) 0.11324(12) 0.0557(6) Uani 1.000000 .
H27 H 0.0214(2) 0.3968(2) 0.13859(12) 0.0669(7) Uiso 1.000000 R
C15 C 0.7036(2) 0.8098(2) 0.21185(13) 0.0590(7) Uani 1.000000 .
H15a H 0.7630(2) 0.7896(2) 0.24620(13) 0.0708(8) Uiso 1.000000 R
H15b H 0.7661(2) 0.8204(2) 0.17747(13) 0.0708(8) Uiso 1.000000 R
C28 C -0.1230(3) 0.5083(3) 0.09949(14) 0.0701(8) Uani 1.000000 .
H28 H -0.2039(3) 0.4706(3) 0.11551(14) 0.0841(10) Uiso 1.000000 R
C29 C -0.1371(3) 0.6066(3) 0.06257(14) 0.0718(8) Uani 1.000000 .
H29 H -0.2280(3) 0.6365(3) 0.05340(14) 0.0862(10) Uiso 1.000000 R
C31 C 0.1170(3) 0.6168(3) 0.05251(13) 0.0749(9) Uani 1.000000 .
H31 H 0.1977(3) 0.6540(3) 0.03594(13) 0.0898(11) Uiso 1.000000 R
C30 C -0.0188(3) 0.6618(3) 0.03883(15) 0.0888(10) Uani 1.000000 .
H30 H -0.0289(3) 0.7293(3) 0.01355(15) 0.1065(12) Uiso 1.000000 R
C24 C 0.4313(4) 0.1900(3) 0.03506(13) 0.0822(9) Uani 1.000000 .
H24a H 0.3399(4) 0.1634(13) 0.0201(6) 0.1233(14) Uiso 1.000000 GR
H24b H 0.4874(18) 0.2230(6) 0.0027(4) 0.1233(14) Uiso 1.000000 GR
H24c H 0.481(2) 0.1212(8) 0.0525(3) 0.1233(14) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O11 C1 1.375(2) .
O11 C12 1.433(2) .
O18 C13 1.457(2) .
O18 C19 1.324(2) .
O21 C20 1.435(2) .
O21 C22 1.353(3) .
C1 C10 1.361(3) .
C1 C2 1.406(3) .
C20 C19 1.520(3) .
C20 C26 1.509(3) .
C9 C4 1.407(3) .
C9 C10 1.415(3) .
C9 C8 1.406(3) .
C4 C3 1.406(3) .
C4 C5 1.423(3) .
C12 C13 1.513(3) .
C12 C17 1.516(3) .
O25 C19 1.187(2) .
C13 C14 1.511(3) .
C2 C3 1.359(3) .
C8 C7 1.368(3) .
C14 C15 1.516(3) .
C26 C27 1.368(3) .
C26 C31 1.367(3) .
C7 C6 1.386(3) .
C17 C16 1.514(3) .
C16 C15 1.513(3) .
C6 C5 1.358(3) .
O23 C22 1.188(3) .
C22 C24 1.481(4) .
C27 C28 1.381(4) .
C28 C29 1.355(4) .
C29 C30 1.362(4) .
C31 C30 1.390(4) .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C12 O11 C1 118.20(16) . .
C19 O18 C13 118.15(16) . .
C22 O21 C20 116.03(17) . .
C10 C1 O11 125.71(18) . .
C2 C1 O11 114.30(19) . .
C2 C1 C10 119.98(19) . .
C19 C20 O21 108.91(16) . .
C26 C20 O21 107.72(16) . .
C26 C20 C19 113.33(17) . .
C10 C9 C4 119.66(19) . .
C8 C9 C4 118.72(18) . .
C8 C9 C10 121.62(19) . .
C3 C4 C9 118.48(18) . .
C5 C4 C9 118.8(2) . .
C5 C4 C3 122.7(2) . .
C13 C12 O11 107.28(16) . .
C17 C12 O11 112.02(17) . .
C17 C12 C13 109.57(15) . .
C9 C10 C1 120.31(18) . .
C12 C13 O18 107.64(15) . .
C14 C13 O18 108.34(16) . .
C14 C13 C12 110.83(17) . .
C20 C19 O18 109.99(17) . .
O25 C19 O18 124.84(19) . .
O25 C19 C20 125.17(19) . .
C3 C2 C1 120.6(2) . .
C7 C8 C9 121.0(2) . .
C2 C3 C4 121.0(2) . .
C15 C14 C13 111.77(19) . .
C27 C26 C20 119.0(2) . .
C31 C26 C20 122.3(2) . .
C31 C26 C27 118.7(2) . .
C6 C7 C8 120.3(2) . .
C16 C17 C12 109.97(17) . .
C15 C16 C17 110.3(2) . .
C5 C6 C7 120.6(2) . .
C6 C5 C4 120.5(2) . .
O23 C22 O21 122.0(2) . .
C24 C22 O21 111.3(2) . .
C24 C22 O23 126.7(3) . .
C28 C27 C26 121.0(2) . .
C16 C15 C14 111.06(18) . .
C29 C28 C27 119.8(3) . .
C30 C29 C28 120.3(3) . .
C30 C31 C26 120.4(3) . .
C31 C30 C29 119.8(3) . .

####################################################################### 
# 
# 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_1051
_database_code_depnum_ccdc_archive 'CCDC 1854342'
_audit_update_record             
;
2018-07-07 deposited with the CCDC.
2019-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H23 Br O3'
_chemical_formula_sum            'C24 H23 Br O3'
_chemical_formula_weight         439.33

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
_chemical_absolute_configuration rm

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   5.8561(5)
_cell_length_b                   8.9674(8)
_cell_length_c                   10.0618(9)
_cell_angle_alpha                94.232(7)
_cell_angle_beta                 97.739(7)
_cell_angle_gamma                98.721(7)
_cell_volume                     515.12(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2363
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.9400
_cell_measurement_theta_min      4.2630
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             226
_exptl_absorpt_coefficient_mu    2.017
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5809
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.23
_diffrn_reflns_theta_max         28.77
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_reflns_number_total             5368
_reflns_number_gt                2450
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0495P)²+0.1998P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.026(11)
_refine_ls_number_reflns         2980
_refine_ls_number_parameters     253
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1119
_refine_ls_wR_factor_gt          0.0997
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br21 Br 1.20971(8) 0.33695(6) 1.08841(6) 0.0771(3) Uani 1 1 d . . .
O18 O 0.8618(6) 0.3462(4) 0.7216(4) 0.0443(8) Uani 1 1 d . . .
O11 O 1.0001(5) 0.2756(4) 0.4778(4) 0.0477(9) Uani 1 1 d . . .
O22 O 1.1941(7) 0.4865(4) 0.8249(4) 0.0629(11) Uani 1 1 d . . .
C28 C 1.0407(10) -0.0226(6) 0.8729(6) 0.0491(13) Uani 1 1 d . . .
H28 H 0.9090 -0.0378 0.9157 0.059 Uiso 1 1 calc R . .
C19 C 1.0476(8) 0.3787(5) 0.8177(5) 0.0356(10) Uani 1 1 d . . .
C8 C 0.9862(8) -0.1318(6) 0.2451(5) 0.0411(11) Uani 1 1 d . . .
C13 C 0.8440(9) 0.4463(5) 0.6156(5) 0.0395(11) Uani 1 1 d . . .
H13 H 0.9906 0.5174 0.6226 0.047 Uiso 1 1 calc R . .
C24 C 1.3447(9) 0.1434(6) 0.7974(6) 0.0499(13) Uani 1 1 d . . .
H24 H 1.4192 0.2409 0.7894 0.060 Uiso 1 1 calc R . .
C27 C 1.1320(12) -0.1445(6) 0.8252(7) 0.0614(16) Uani 1 1 d . . .
H27 H 1.0614 -0.2424 0.8349 0.074 Uiso 1 1 calc R . .
C4 C 0.5986(9) -0.1226(6) 0.1246(5) 0.0448(12) Uani 1 1 d . . .
H4 H 0.4687 -0.0747 0.1087 0.054 Uiso 1 1 calc R . .
C6 C 0.7953(10) -0.3299(7) 0.0746(6) 0.0536(14) Uani 1 1 d . . .
H6 H 0.7958 -0.4216 0.0250 0.064 Uiso 1 1 calc R . .
C3 C 0.7888(8) -0.0555(6) 0.2233(5) 0.0397(11) Uani 1 1 d . . .
C23 C 1.1444(8) 0.1229(5) 0.8574(5) 0.0350(10) Uani 1 1 d . . .
C2 C 0.7875(8) 0.0815(6) 0.3014(5) 0.0399(11) Uani 1 1 d . . .
H2 H 0.6584 0.1306 0.2886 0.048 Uiso 1 1 calc R . .
C5 C 0.6033(10) -0.2571(6) 0.0522(6) 0.0507(13) Uani 1 1 d . . .
H5 H 0.4768 -0.2998 -0.0124 0.061 Uiso 1 1 calc R . .
C12 C 0.8008(8) 0.3499(6) 0.4803(5) 0.0401(11) Uani 1 1 d . . .
H12 H 0.6594 0.2742 0.4751 0.048 Uiso 1 1 calc R . .
C17 C 0.7718(9) 0.4514(6) 0.3686(5) 0.0478(12) Uani 1 1 d . . .
H17A H 0.7406 0.3902 0.2826 0.057 Uiso 1 1 calc R . .
H17B H 0.9161 0.5213 0.3708 0.057 Uiso 1 1 calc R . .
C9 C 1.1724(9) -0.0646(6) 0.3445(6) 0.0492(13) Uani 1 1 d . . .
H9 H 1.3020 -0.1128 0.3606 0.059 Uiso 1 1 calc R . .
C25 C 1.4333(11) 0.0210(8) 0.7500(7) 0.0646(17) Uani 1 1 d . . .
H25 H 1.5667 0.0354 0.7086 0.077 Uiso 1 1 calc R . .
C1 C 0.9746(8) 0.1423(6) 0.3957(5) 0.0399(11) Uani 1 1 d . . .
C16 C 0.5735(11) 0.5406(7) 0.3812(6) 0.0585(15) Uani 1 1 d . . .
H16A H 0.4267 0.4714 0.3717 0.070 Uiso 1 1 calc R . .
H16B H 0.5634 0.6073 0.3097 0.070 Uiso 1 1 calc R . .
C20 C 1.0419(9) 0.2540(5) 0.9103(5) 0.0407(11) Uani 1 1 d . . .
H20 H 0.8787 0.2178 0.9193 0.049 Uiso 1 1 calc R . .
C7 C 0.9826(10) -0.2699(6) 0.1675(6) 0.0512(14) Uani 1 1 d . . .
H7 H 1.1101 -0.3205 0.1803 0.061 Uiso 1 1 calc R . .
C14 C 0.6468(10) 0.5332(7) 0.6302(5) 0.0541(14) Uani 1 1 d . . .
H14A H 0.6795 0.5949 0.7160 0.065 Uiso 1 1 calc R . .
H14B H 0.5035 0.4626 0.6293 0.065 Uiso 1 1 calc R . .
C15 C 0.6149(13) 0.6339(8) 0.5173(6) 0.0667(17) Uani 1 1 d . . .
H15A H 0.7530 0.7102 0.5229 0.080 Uiso 1 1 calc R . .
H15B H 0.4827 0.6853 0.5266 0.080 Uiso 1 1 calc R . .
C10 C 1.1702(8) 0.0664(6) 0.4170(5) 0.0466(12) Uani 1 1 d . . .
H10 H 1.2973 0.1078 0.4816 0.056 Uiso 1 1 calc R . .
C26 C 1.3275(14) -0.1220(8) 0.7630(6) 0.0698(19) Uani 1 1 d . . .
H26 H 1.3879 -0.2049 0.7296 0.084 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
Br21 C20 1.959(5) . ?
O18 C19 1.335(6) . ?
O18 C13 1.446(6) . ?
O11 C1 1.379(6) . ?
O11 C12 1.431(5) . ?
O22 C19 1.182(6) . ?
C28 C27 1.371(8) . ?
C28 C23 1.382(7) . ?
C19 C20 1.507(7) . ?
C8 C9 1.404(8) . ?
C8 C7 1.411(7) . ?
C8 C3 1.430(6) . ?
C13 C14 1.504(7) . ?
C13 C12 1.527(6) . ?
C24 C25 1.366(8) . ?
C24 C23 1.384(7) . ?
C27 C26 1.373(10) . ?
C4 C5 1.368(7) . ?
C4 C3 1.414(7) . ?
C6 C7 1.355(8) . ?
C6 C5 1.385(8) . ?
C3 C2 1.410(7) . ?
C23 C20 1.495(6) . ?
C2 C1 1.364(7) . ?
C12 C17 1.506(7) . ?
C17 C16 1.521(7) . ?
C9 C10 1.339(7) . ?
C25 C26 1.361(10) . ?
C1 C10 1.419(7) . ?
C16 C15 1.521(8) . ?
C14 C15 1.512(8) . ?

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
C19 O18 C13 117.7(4) . . ?
C1 O11 C12 118.0(4) . . ?
C27 C28 C23 120.0(5) . . ?
O22 C19 O18 124.6(4) . . ?
O22 C19 C20 126.5(4) . . ?
O18 C19 C20 108.9(4) . . ?
C9 C8 C7 123.7(5) . . ?
C9 C8 C3 117.6(5) . . ?
C7 C8 C3 118.7(5) . . ?
O18 C13 C14 109.4(4) . . ?
O18 C13 C12 108.2(4) . . ?
C14 C13 C12 111.0(4) . . ?
C25 C24 C23 120.2(5) . . ?
C28 C27 C26 120.0(6) . . ?
C5 C4 C3 120.8(5) . . ?
C7 C6 C5 121.1(5) . . ?
C2 C3 C4 122.2(4) . . ?
C2 C3 C8 119.6(4) . . ?
C4 C3 C8 118.2(4) . . ?
C28 C23 C24 119.2(4) . . ?
C28 C23 C20 119.1(4) . . ?
C24 C23 C20 121.8(4) . . ?
C1 C2 C3 120.3(4) . . ?
C4 C5 C6 120.3(5) . . ?
O11 C12 C17 112.7(4) . . ?
O11 C12 C13 105.6(4) . . ?
C17 C12 C13 109.0(4) . . ?
C12 C17 C16 111.8(4) . . ?
C10 C9 C8 122.3(4) . . ?
C26 C25 C24 120.4(6) . . ?
C2 C1 O11 127.0(4) . . ?
C2 C1 C10 120.0(5) . . ?
O11 C1 C10 113.1(4) . . ?
C17 C16 C15 110.2(5) . . ?
C23 C20 C19 112.3(4) . . ?
C23 C20 Br21 110.4(3) . . ?
C19 C20 Br21 108.9(3) . . ?
C6 C7 C8 120.7(5) . . ?
C13 C14 C15 111.0(5) . . ?
C14 C15 C16 110.5(5) . . ?
C9 C10 C1 120.3(5) . . ?
C25 C26 C27 120.2(5) . . ?

_diffrn_measured_fraction_theta_max 0.865
_diffrn_reflns_theta_full        28.77
_diffrn_measured_fraction_theta_full 1.0
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_973
_database_code_depnum_ccdc_archive 'CCDC 1854339'
_audit_update_record             
;
2018-07-07 deposited with the CCDC.
2019-02-08 downloaded from the CCDC.
;
_chemical_formula_moiety         'C19 H21 Cl O3'
_chemical_formula_sum            'C19 H21 Cl O3'
_chemical_formula_weight         332.83
_chemical_absolute_configuration rm
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_cell_length_a                   8.8657(9)
_cell_length_b                   10.5557(9)
_cell_length_c                   18.970(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1775.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2163
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.9400
_cell_measurement_theta_min      4.2630
_exptl_absorpt_coefficient_mu    0.227
_exptl_crystal_density_diffrn    1.2452
_exptl_crystal_F_000             704.9279
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11056
_diffrn_reflns_theta_full        29.0891
_diffrn_reflns_theta_max         29.09
_diffrn_reflns_theta_min         3.19
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 0.8623
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_reflns_Friedel_coverage         0.811
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              24
_reflns_limit_l_min              -24
_reflns_number_gt                2615
_reflns_number_total             4101
_reflns_threshold_expression     I>=2u(I)
_refine_diff_density_max         0.5736
_refine_diff_density_min         -0.4648
_refine_diff_density_rms         0.0687
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.16(14)
_refine_ls_d_res_high            0.7309
_refine_ls_d_res_low             6.3919
_refine_ls_goodness_of_fit_ref   0.9575
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     212
_refine_ls_number_reflns         4101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.0699
_refine_ls_restrained_S_all      0.9575
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1033P)²+0.6623P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2009
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  H4 of C4, H10 of C10, H5 of C5, H12 of C12, H17 of C17, H9 of C9, {H13a,
  H13b} of C13, H6 of C6, {H16a,H16b} of C16, H20 of C20, H7 of C7, {H14a,H14b}
  of C14, {H15a,H15b} of C15
 At 1.5 times of:
  {H22a,H22b,H22c} of C22
2.a Ternary CH refined with riding coordinates:
 C12(H12), C17(H17), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b), C16(H16a,H16b), C14(H14a,H14b), C15(H15a,H15b)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C10(H10), C5(H5), C9(H9), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C22(H22a,H22b,H22c)
;
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_refinement_flags_posn
Cl21 Cl 0.8526(3) 0.80354(14) 0.42878(8) 0.1441(9) Uani 1.000000 .
C19 C 0.7229(5) 0.5764(4) 0.4138(2) 0.0676(11) Uani 1.000000 .
O18 O 0.7625(2) 0.4605(2) 0.39864(14) 0.0606(7) Uani 1.000000 .
O11 O 0.6027(3) 0.2883(2) 0.47766(12) 0.0590(7) Uani 1.000000 .
O23 O 0.6051(4) 0.6223(3) 0.3990(3) 0.1331(18) Uani 1.000000 .
C1 C 0.7052(4) 0.0948(4) 0.5273(3) 0.0621(10) Uani 1.000000 .
C2 C 0.6411(4) 0.2128(3) 0.53287(18) 0.0515(8) Uani 1.000000 .
C3 C 0.6115(3) 0.2667(3) 0.60018(19) 0.0465(7) Uani 1.000000 .
C4 C 0.5526(4) 0.3899(3) 0.60805(19) 0.0524(8) Uani 1.000000 .
H4 H 0.5280(4) 0.4369(3) 0.56820(19) 0.0629(10) Uiso 1.000000 R
C10 C 0.7401(4) 0.0266(4) 0.5878(3) 0.0699(11) Uani 1.000000 .
H10 H 0.7841(4) -0.0530(4) 0.5836(3) 0.0839(13) Uiso 1.000000 R
C5 C 0.5312(5) 0.4410(4) 0.6730(2) 0.0659(10) Uani 1.000000 .
H5 H 0.4932(5) 0.5228(4) 0.6773(2) 0.0790(12) Uiso 1.000000 R
C12 C 0.6488(4) 0.2558(3) 0.40719(18) 0.0504(8) Uani 1.000000 .
H12 H 0.7503(4) 0.2191(3) 0.40827(18) 0.0605(10) Uiso 1.000000 R
C17 C 0.6512(4) 0.3770(3) 0.36603(17) 0.0473(8) Uani 1.000000 .
H17 H 0.5514(4) 0.4168(3) 0.36790(17) 0.0568(9) Uiso 1.000000 R
C9 C 0.7114(5) 0.0735(4) 0.6523(3) 0.0730(13) Uani 1.000000 .
H9 H 0.7334(5) 0.0247(4) 0.6918(3) 0.0876(15) Uiso 1.000000 R
C8 C 0.6486(4) 0.1957(4) 0.6614(2) 0.0582(9) Uani 1.000000 .
C13 C 0.5406(4) 0.1633(4) 0.3730(2) 0.0663(10) Uani 1.000000 .
H13a H 0.5414(4) 0.0841(4) 0.3989(2) 0.0795(12) Uiso 1.000000 R
H13b H 0.4391(4) 0.1975(4) 0.3747(2) 0.0795(12) Uiso 1.000000 R
C6 C 0.5659(5) 0.3714(5) 0.7333(2) 0.0739(12) Uani 1.000000 .
H6 H 0.5500(5) 0.4067(5) 0.7776(2) 0.0887(14) Uiso 1.000000 R
C16 C 0.6956(5) 0.3551(4) 0.2900(2) 0.0675(11) Uani 1.000000 .
H16a H 0.6932(5) 0.4349(4) 0.2647(2) 0.0810(13) Uiso 1.000000 R
H16b H 0.7977(5) 0.3224(4) 0.2881(2) 0.0810(13) Uiso 1.000000 R
C20 C 0.8505(5) 0.6413(4) 0.4538(3) 0.0771(12) Uani 1.000000 .
H20 H 0.9467(5) 0.6021(4) 0.4406(3) 0.0925(15) Uiso 1.000000 R
C7 C 0.6224(5) 0.2531(5) 0.7278(2) 0.0733(12) Uani 1.000000 .
H7 H 0.6447(5) 0.2081(5) 0.7686(2) 0.0880(15) Uiso 1.000000 R
C14 C 0.5851(5) 0.1388(5) 0.2965(3) 0.0850(14) Uani 1.000000 .
H14a H 0.6838(5) 0.0992(5) 0.2949(3) 0.1020(17) Uiso 1.000000 R
H14b H 0.5131(5) 0.0814(5) 0.2750(3) 0.1020(17) Uiso 1.000000 R
C15 C 0.5890(6) 0.2619(5) 0.2553(3) 0.0860(15) Uani 1.000000 .
H15a H 0.4884(6) 0.2979(5) 0.2533(3) 0.1032(18) Uiso 1.000000 R
H15b H 0.6220(6) 0.2454(5) 0.2074(3) 0.1032(18) Uiso 1.000000 R
C22 C 0.8311(7) 0.6331(6) 0.5319(3) 0.1080(19) Uani 1.000000 .
H22a H 0.919(2) 0.667(4) 0.5547(3) 0.162(3) Uiso 1.000000 GR
H22b H 0.744(3) 0.681(3) 0.5457(4) 0.162(3) Uiso 1.000000 GR
H22c H 0.818(5) 0.5461(7) 0.5453(4) 0.162(3) Uiso 1.000000 GR
H1 H 0.733(4) 0.062(3) 0.485(2) 0.050(10) Uiso 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl21 C20 1.777(5) .
C19 O18 1.306(4) .
C19 O23 1.185(5) .
C19 C20 1.523(6) .
O18 C17 1.461(4) .
O11 C2 1.359(4) .
O11 C12 1.439(4) .
C1 C2 1.373(5) .
C1 C10 1.389(6) .
C2 C3 1.422(5) .
C3 C4 1.409(5) .
C3 C8 1.420(5) .
C4 C5 1.359(5) .
C10 C9 1.344(6) .
C5 C6 1.394(6) .
C12 C17 1.499(5) .
C12 C13 1.514(5) .
C17 C16 1.512(5) .
C9 C8 1.415(6) .
C8 C7 1.417(6) .
C13 C14 1.527(7) .
C6 C7 1.350(7) .
C16 C15 1.515(6) .
C20 C22 1.494(7) .
C14 C15 1.516(8) .

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
O23 C19 O18 124.5(4) . .
C20 C19 O18 109.4(4) . .
C20 C19 O23 126.1(4) . .
C17 O18 C19 118.6(3) . .
C12 O11 C2 120.3(2) . .
C10 C1 C2 119.9(4) . .
C1 C2 O11 125.2(3) . .
C3 C2 O11 114.3(3) . .
C3 C2 C1 120.5(3) . .
C4 C3 C2 122.2(3) . .
C8 C3 C2 118.7(3) . .
C8 C3 C4 119.1(3) . .
C5 C4 C3 121.0(4) . .
C9 C10 C1 121.3(4) . .
C6 C5 C4 120.2(4) . .
C17 C12 O11 106.5(2) . .
C13 C12 O11 111.8(3) . .
C13 C12 C17 109.6(3) . .
C12 C17 O18 107.7(3) . .
C16 C17 O18 108.7(3) . .
C16 C17 C12 111.7(3) . .
C8 C9 C10 121.4(4) . .
C9 C8 C3 118.2(4) . .
C7 C8 C3 117.6(4) . .
C7 C8 C9 124.2(4) . .
C14 C13 C12 110.7(3) . .
C7 C6 C5 120.4(4) . .
C15 C16 C17 110.6(3) . .
C19 C20 Cl21 107.9(3) . .
C22 C20 Cl21 108.8(4) . .
C22 C20 C19 112.4(4) . .
C6 C7 C8 121.7(4) . .
C15 C14 C13 110.5(4) . .
C14 C15 C16 110.2(4) . .

