# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_mx5492
_database_code_depnum_ccdc_archive 'CCDC 1887020'
loop_
_audit_author_name
_audit_author_address
'Qing Zhang'
;Institute of Chemistry Chinese Academy of Science
China
;
_audit_update_record             
;
2018-12-23 deposited with the CCDC.	2020-01-08 downloaded from the CCDC.
;
_audit_creation_date             2017-01-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        1,4-diethynyl-2,5-bis(hexyloxy)benzene
_chemical_formula_moiety         'C22 H30 O2'
_chemical_formula_sum            'C22 H30 O2'
_chemical_formula_weight         326.46
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.223(4)
_cell_length_b                   6.718(3)
_cell_length_c                   15.694(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.983(7)
_cell_angle_gamma                90
_cell_volume                     972.2(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2594
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.5
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.808
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.115
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.216
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.031
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7335
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.472
_diffrn_reflns_theta_min         2.543
_diffrn_ambient_temperature      173
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 44.9541
	          2theta: -19.7082
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 44.9541
	          2theta: -19.7082
;
_diffrn_measurement_device       
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
'MM007-HF CCD(Saturn 724+)'
;
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.057931
_diffrn_orient_matrix_UB_12      -0.063720
_diffrn_orient_matrix_UB_13      -0.065906
_diffrn_orient_matrix_UB_21      0.087573
_diffrn_orient_matrix_UB_22      0.115321
_diffrn_orient_matrix_UB_23      -0.034519
_diffrn_orient_matrix_UB_31      0.039265
_diffrn_orient_matrix_UB_32      -0.015531
_diffrn_orient_matrix_UB_33      0.047730
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1936
_reflns_number_total             2210
_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       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2014)'
_computing_structure_solution    'ShelXT (Sheldrick, 2014)'
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.251
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         2210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0788
_refine_ls_restrained_S_all      1.251
_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)+(0.0330P)²+0.4900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1393
_refine_ls_wR_factor_ref         0.1453
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
2.d :
 C1(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
O1 O 0.51393(16) 0.6567(2) 0.83679(8) 0.0366(4) Uani 1 1 d . . . . .
C1 C 0.2974(2) 0.2288(3) 0.80323(13) 0.0374(5) Uani 1 1 d . . . . .
H1 H 0.2487 0.1631 0.7591 0.045 Uiso 1 1 calc R . . . .
C2 C 0.3594(2) 0.3125(3) 0.85934(12) 0.0314(5) Uani 1 1 d . . . . .
C3 C 0.4316(2) 0.4087(3) 0.93012(11) 0.0288(4) Uani 1 1 d . . . . .
C4 C 0.5109(2) 0.5843(3) 0.91834(12) 0.0306(4) Uani 1 1 d . . . . .
C5 C 0.5788(2) 0.6736(3) 0.98806(12) 0.0308(5) Uani 1 1 d . . . . .
H5 H 0.6319 0.7898 0.9804 0.037 Uiso 1 1 calc R . . . .
C6 C 0.5929(2) 0.8385(3) 0.82323(12) 0.0347(5) Uani 1 1 d . . . . .
H6A H 0.6950 0.8192 0.8366 0.042 Uiso 1 1 calc R . . . .
H6B H 0.5562 0.9433 0.8595 0.042 Uiso 1 1 calc R . . . .
C7 C 0.5726(2) 0.8944(3) 0.73044(12) 0.0343(5) Uani 1 1 d . . . . .
H7A H 0.6135 1.0257 0.7217 0.041 Uiso 1 1 calc R . . . .
H7B H 0.4695 0.9026 0.7176 0.041 Uiso 1 1 calc R . . . .
C8 C 0.6410(2) 0.7510(3) 0.66797(12) 0.0362(5) Uani 1 1 d . . . . .
H8A H 0.6086 0.6169 0.6804 0.043 Uiso 1 1 calc R . . . .
H8B H 0.7455 0.7544 0.6759 0.043 Uiso 1 1 calc R . . . .
C9 C 0.6034(2) 0.7999(3) 0.57531(12) 0.0350(5) Uani 1 1 d . . . . .
H9A H 0.4991 0.7918 0.5672 0.042 Uiso 1 1 calc R . . . .
H9B H 0.6323 0.9359 0.5638 0.042 Uiso 1 1 calc R . . . .
C10 C 0.6752(2) 0.6632(3) 0.51154(13) 0.0390(5) Uani 1 1 d . . . . .
H10A H 0.6466 0.5271 0.5231 0.047 Uiso 1 1 calc R . . . .
H10B H 0.7796 0.6718 0.5193 0.047 Uiso 1 1 calc R . . . .
C11 C 0.6362(3) 0.7133(4) 0.41917(13) 0.0458(6) Uani 1 1 d . . . . .
H11A H 0.6845 0.6223 0.3820 0.069 Uiso 1 1 calc GR . . . .
H11B H 0.6664 0.8468 0.4068 0.069 Uiso 1 1 calc GR . . . .
H11C H 0.5333 0.7022 0.4106 0.069 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
O1 C4 1.370(2) . ?
O1 C6 1.440(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.184(3) . ?
C2 C3 1.439(3) . ?
C3 C4 1.401(3) . ?
C3 C5 1.403(3) 3_667 ?
C4 C5 1.388(3) . ?
C5 C3 1.403(3) 3_667 ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.512(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.519(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.525(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.518(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.525(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
C4 O1 C6 117.26(15) . . ?
C2 C1 H1 180.0 . . ?
C1 C2 C3 177.5(2) . . ?
C4 C3 C2 120.79(17) . . ?
C4 C3 C5 119.77(17) . 3_667 ?
C5 C3 C2 119.43(18) 3_667 . ?
O1 C4 C3 116.20(16) . . ?
O1 C4 C5 124.50(19) . . ?
C5 C4 C3 119.30(17) . . ?
C3 C5 H5 119.5 3_667 . ?
C4 C5 C3 120.93(19) . 3_667 ?
C4 C5 H5 119.5 . . ?
O1 C6 H6A 110.2 . . ?
O1 C6 H6B 110.2 . . ?
O1 C6 C7 107.33(16) . . ?
H6A C6 H6B 108.5 . . ?
C7 C6 H6A 110.2 . . ?
C7 C6 H6B 110.2 . . ?
C6 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
C6 C7 C8 114.70(17) . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C7 C8 C9 112.87(17) . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C8 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 C8 113.82(17) . . ?
C10 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C9 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
C9 C10 C11 113.27(18) . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
