# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_4-Chloro
_database_code_depnum_ccdc_archive 'CCDC 1045015'
_audit_update_record             
;
2015-01-22 deposited with the CCDC.
2015-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 Cl N2 O3'
_chemical_formula_weight         382.83

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.1999(5)
_cell_length_b                   13.2765(11)
_cell_length_c                   23.277(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1916.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             800.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.223
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11558
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.750
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             3390
_reflns_number_gt                2041
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.976

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0742P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 643 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3390
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1515
_refine_ls_wR_factor_gt          0.1235
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.5093(4) 0.74056(12) 0.40738(7) 0.1023(7) Uani 1 1 d . . . . .
O1 O 0.5511(6) 0.1896(2) 0.55731(13) 0.0541(9) Uani 1 1 d . . . . .
O2 O 0.6029(5) 0.2562(3) 0.47307(14) 0.0604(10) Uani 1 1 d . . . . .
O3 O 0.7383(6) 0.7389(3) 0.73270(17) 0.0767(12) Uani 1 1 d . . . . .
N2 N 0.5097(9) 0.1052(3) 0.64364(18) 0.0659(13) Uani 1 1 d . . . . .
C6 C 0.5903(8) 0.4776(4) 0.6421(2) 0.0454(12) Uani 1 1 d . . . . .
C1 C 0.5943(7) 0.2705(4) 0.5245(2) 0.0485(13) Uani 1 1 d . . . . .
C13 C 0.6135(9) 0.4605(4) 0.5134(2) 0.0491(13) Uani 1 1 d . . . . .
C2 C 0.6431(8) 0.3701(3) 0.5524(2) 0.0469(12) Uani 1 1 d . . . . .
H2 H 0.7973 0.3683 0.5616 0.056 Uiso 1 1 calc R U . . .
C3 C 0.5251(8) 0.3837(3) 0.61094(19) 0.0485(12) Uani 1 1 d . . . . .
H3 H 0.3701 0.3883 0.6030 0.058 Uiso 1 1 calc R U . . .
C9 C 0.7036(9) 0.6515(4) 0.7030(2) 0.0558(14) Uani 1 1 d . . . . .
C7 C 0.7902(9) 0.4902(4) 0.6662(2) 0.0622(15) Uani 1 1 d . . . . .
H7 H 0.8909 0.4389 0.6619 0.075 Uiso 1 1 calc R U . . .
C8 C 0.8500(9) 0.5748(4) 0.6964(2) 0.0591(14) Uani 1 1 d . . . . .
H8 H 0.9874 0.5800 0.7121 0.071 Uiso 1 1 calc R U . . .
C5 C 0.4679(9) 0.1993(4) 0.61559(19) 0.0561(13) Uani 1 1 d . . . . .
H5 H 0.3113 0.2086 0.6134 0.067 Uiso 1 1 calc R U . . .
C4 C 0.5627(9) 0.2886(4) 0.6462(2) 0.0552(13) Uani 1 1 d . . . . .
H4A H 0.7163 0.2784 0.6517 0.066 Uiso 1 1 calc R U . . .
H4B H 0.4961 0.2958 0.6836 0.066 Uiso 1 1 calc R U . . .
C19 C 0.6997(11) 0.0838(4) 0.6671(2) 0.0656(17) Uani 1 1 d . . . . .
H19 H 0.8208 0.1250 0.6687 0.079 Uiso 1 1 calc R U . . .
C18 C 0.7756(9) 0.5300(4) 0.5070(2) 0.0606(15) Uani 1 1 d . . . . .
H18 H 0.9090 0.5186 0.5241 0.073 Uiso 1 1 calc R U . . .
C14 C 0.4168(9) 0.4785(4) 0.4867(2) 0.0629(15) Uani 1 1 d . . . . .
H14 H 0.3052 0.4322 0.4908 0.075 Uiso 1 1 calc R U . . .
C16 C 0.5482(11) 0.6331(4) 0.4487(2) 0.0637(15) Uani 1 1 d . . . . .
C11 C 0.4482(9) 0.5563(4) 0.6479(2) 0.0656(16) Uani 1 1 d . . . . .
H11 H 0.3124 0.5518 0.6311 0.079 Uiso 1 1 calc R U . . .
C15 C 0.3847(11) 0.5648(5) 0.4540(2) 0.0702(16) Uani 1 1 d . . . . .
H15 H 0.2530 0.5760 0.4360 0.084 Uiso 1 1 calc R U . . .
C10 C 0.5030(10) 0.6424(4) 0.6782(3) 0.0734(17) Uani 1 1 d . . . . .
H10 H 0.4035 0.6944 0.6819 0.088 Uiso 1 1 calc R U . . .
C17 C 0.7420(11) 0.6180(5) 0.4751(2) 0.0702(16) Uani 1 1 d . . . . .
H17 H 0.8510 0.6658 0.4719 0.084 Uiso 1 1 calc R U . . .
N1 N 0.3660(13) 0.0277(5) 0.6483(3) 0.118(2) Uani 1 1 d . . . . .
C12 C 0.9441(11) 0.7525(5) 0.7578(3) 0.093(2) Uani 1 1 d . . . . .
H12A H 0.9687 0.7010 0.7859 0.139 Uiso 1 1 calc R U . . .
H12B H 0.9504 0.8174 0.7759 0.139 Uiso 1 1 calc R U . . .
H12C H 1.0529 0.7485 0.7285 0.139 Uiso 1 1 calc R U . . .
C21 C 0.478(2) -0.0458(6) 0.6768(3) 0.113(3) Uani 1 1 d . . . . .
H21 H 0.4277 -0.1093 0.6872 0.135 Uiso 1 1 calc R U . . .
C20 C 0.680(2) -0.0072(6) 0.6871(3) 0.115(3) Uani 1 1 d . . . . .
H20 H 0.7888 -0.0418 0.7061 0.138 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
Cl1 C16 1.737(5) . ?
O1 C1 1.345(6) . ?
O1 C5 1.457(6) . ?
O2 C1 1.213(5) . ?
O3 C9 1.368(6) . ?
O3 C12 1.415(7) . ?
N2 C19 1.328(7) . ?
N2 N1 1.364(7) . ?
N2 C5 1.434(6) . ?
C6 C7 1.370(7) . ?
C6 C11 1.374(7) . ?
C6 C3 1.499(6) . ?
C1 C2 1.504(7) . ?
C13 C18 1.372(7) . ?
C13 C14 1.389(7) . ?
C13 C2 1.516(6) . ?
C2 C3 1.558(6) . ?
C2 H2 0.9800 . ?
C3 C4 1.523(6) . ?
C3 H3 0.9800 . ?
C9 C8 1.372(7) . ?
C9 C10 1.375(7) . ?
C7 C8 1.376(7) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C5 C4 1.503(7) . ?
C5 H5 0.9800 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C19 C20 1.301(9) . ?
C19 H19 0.9300 . ?
C18 C17 1.400(8) . ?
C18 H18 0.9300 . ?
C14 C15 1.390(7) . ?
C14 H14 0.9300 . ?
C16 C17 1.365(8) . ?
C16 C15 1.366(8) . ?
C11 C10 1.386(7) . ?
C11 H11 0.9300 . ?
C15 H15 0.9300 . ?
C10 H10 0.9300 . ?
C17 H17 0.9300 . ?
N1 C21 1.371(10) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C21 C20 1.372(12) . ?
C21 H21 0.9300 . ?
C20 H20 0.9300 . ?

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 O1 C5 121.9(4) . . ?
C9 O3 C12 117.4(5) . . ?
C19 N2 N1 112.7(5) . . ?
C19 N2 C5 122.2(5) . . ?
N1 N2 C5 125.1(6) . . ?
C7 C6 C11 116.6(5) . . ?
C7 C6 C3 123.0(4) . . ?
C11 C6 C3 120.5(4) . . ?
O2 C1 O1 116.3(4) . . ?
O2 C1 C2 123.7(5) . . ?
O1 C1 C2 119.8(4) . . ?
C18 C13 C14 118.6(5) . . ?
C18 C13 C2 120.6(4) . . ?
C14 C13 C2 120.6(5) . . ?
C1 C2 C13 114.4(4) . . ?
C1 C2 C3 112.6(4) . . ?
C13 C2 C3 112.1(4) . . ?
C1 C2 H2 105.6 . . ?
C13 C2 H2 105.6 . . ?
C3 C2 H2 105.6 . . ?
C6 C3 C4 112.8(4) . . ?
C6 C3 C2 113.1(4) . . ?
C4 C3 C2 107.7(4) . . ?
C6 C3 H3 107.7 . . ?
C4 C3 H3 107.7 . . ?
C2 C3 H3 107.7 . . ?
O3 C9 C8 125.5(5) . . ?
O3 C9 C10 115.4(5) . . ?
C8 C9 C10 119.1(5) . . ?
C6 C7 C8 123.5(5) . . ?
C6 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C9 C8 C7 118.9(5) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
N2 C5 O1 106.5(4) . . ?
N2 C5 C4 113.7(4) . . ?
O1 C5 C4 111.8(4) . . ?
N2 C5 H5 108.2 . . ?
O1 C5 H5 108.2 . . ?
C4 C5 H5 108.2 . . ?
C5 C4 C3 109.8(4) . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C20 C19 N2 105.1(7) . . ?
C20 C19 H19 127.4 . . ?
N2 C19 H19 127.4 . . ?
C13 C18 C17 120.6(5) . . ?
C13 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C13 C14 C15 120.8(5) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C17 C16 C15 121.0(5) . . ?
C17 C16 Cl1 119.5(5) . . ?
C15 C16 Cl1 119.5(5) . . ?
C6 C11 C10 121.3(5) . . ?
C6 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C16 C15 C14 119.4(5) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C9 C10 C11 120.5(5) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C16 C17 C18 119.5(6) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
N2 N1 C21 104.1(7) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C21 C20 106.2(7) . . ?
N1 C21 H21 126.9 . . ?
C20 C21 H21 126.9 . . ?
C19 C20 C21 111.8(8) . . ?
C19 C20 H20 124.1 . . ?
C21 C20 H20 124.1 . . ?

_refine_diff_density_max         0.190
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.052

_shelxl_version_number           2014/6



